Patent Publication Number: US-5633355-A

Title: Monoazo disperse dyes from selected (aromatic amino)propionates or selected (aromatic amino)butyrates

Description:
This is a continuation of application Ser. No. 08/373,171, filed Jan. 17, 1995, now abandoned. 
    
    
     The invention relates to the disperse dyes of the general formula I ##STR2## wherein D signifies a diazo component which is usual with disperse dyes, 
     K signifies an aromatic radical of formula ##STR3## R 1  signifies hydrogen, chlorine, C 1-2  -alkyl, C 1-2  -alkoxy or acylamino, 
     R 2  signifies hydrogen, C 1-4  -alkoxy, C 1-2  -alkoxyethoxy, chlorine, bromine, or together with R 3  signifies a group of formula --*CH(CH 3 )CH 2  C(CH 3 ) 2  -- (*bonded to the nucleus), 
     R 3  signifies hydrogen, C 1-6  -alkyl, C 3-4  -alkenyl, chloro- or bromo-C 3-4  -alkenyl, C 3-4  -alkinyl, phenyl-C 1-3  -alkyl, C 1-4  -alkoxycarbonyl-C 1-3  -alkyl, C 3-4  -alkenyloxycarbonyl-C 1-3  -alkyl, C 3-4  -alkinyloxycarbonyl-C 1-3  -alkyl, phenoxy-C 2-4  -alkyl; C 2-4  -alkyl substituted by halogen, cyano, C 1-4  -alkoxy, C 1-4  -alkylcarbonyloxy or C 1-4  -alkoxycarbonyloxy; or a group of formula --CH 2  --CH(R 8 )CH 2  --R 9 , 
     R 4  signifies hydrogen, phenyl or C 1-2  -alkyl, 
     R 5  signifies a radical of formula ##STR4## R 6  signifies hydrogen or hydroxyl, R 7  signifies hydrogen or C 1-4  -alkyl, 
     R 8  signifies hydroxyl, C 1-4  -alkylcarbonyloxy or C 1-4  -alkoxycarbonyloxy, 
     R 9  signifies chlorine, C 1-4  -alkoxy, phenoxy, allyloxy or C 1-4  -alkylcarbonyloxy, 
     R 10  signifies hydrogen or C 1-4  -alkyl, 
     Y signifies C 2-3  -alkylene, 
     m and z independently signify zero or 1 and 
     n signifies a number from 1 to 5, with the proviso that, if K is a radical of formula b or c, R 3  only signifies hydrogen 
     One group of preferred dyestuffs of formula I corresponds to the general formula Ia ##STR5## wherein D 1  is 3-phenyl-1,2,4-thiadiazolyl or corresponds to one of the following formulae: ##STR6## wherein a signifies hydrogen, chlorine, bromine, cyano, nitro-, C 1-4  -alkoxycarbonyl, C 1-3  -alkylsulphonyl, preferably hydrogen, chlorine, cyano or nitro, 
     b signifies chlorine, bromine, nitro, methyl, C 1-2  -alkylsulphonyl, C 1-4  -alkylcarbonyl, aminosulphonyl, mono- or di-C 1-4  -alkylaminosulphonyl, phenylaminosulphonyl, C 1-4  -alkoxycarbonyl, aminocarbonyl, mono- or di-C 1-4  -alkylaminocarbonyl, phenylaminocarbonyl, phenylazo, benzyloxycarbonyl, tetrahydrofurfuryl-2-oxycarbonyl, C 3-4  -alkenyloxycarbonyl, C 3-4  -alkinyloxycarbonyl or phenoxycarbonyl, 
     c signifies hydrogen or chlorine, or if d is hydrogen, also thiocyano, 
     d signifies hydrogen, chlorine, bromine or cyano, 
     e signifies nitro, C 1-4  -alkylcarbonyl, C 1-4  -alkoxycarbonyl, cyano, aminocarbonyl, mono- or di-C 1-4  -alkylaminocarbonyl, 
     f signifies hydrogen, chlorine, bromine, C 1-2  -alkyl or phenyl, 
     g signifies nitro, cyano, formyl, dicyanovinyl or a group of formula --CH═CH--NO 2 , --CH═C(CN)CO--OC 1-4  -alkyl, H 5  C 6  --N═N-- or 3- or 4-NO 2  --C 6  H 4  --N═N--, 
     h signifies cyano or C 1-4  -alkoxycarbonyl, 
     i signifies C 1-4  -alkyl or phenyl, 
     j signifies --CN, --CH═CH 2  or phenyl, 
     k signifies C 1-4  -alkyl, 
     l signifies hydrogen, chlorine, bromine, cyano, thiocyano, nitro, C 1-4  -alkoxycarbonyl or di-C 1-4  -alkylaminosulphonyl, 
     p signifies hydrogen, chlorine or bromine and 
     q signifies C 1-4  -alkyl, C 1-4  -alkoxycarbonyl-C 1-4  -alkylene or C 1-4  -alkylene-COOCH 2  CF 3 , 
     whereby the phenyl nuclei of these substituents may bear one or two substituents from the series chlorine, bromine, methyl or C 1-2  -alkoxy, 
     R 1  &#39; signifies hydrogen, C 1-2  -akyl, chlorine or acylamino, 
     R 2  &#39; signifies hydrogen, chlorine, C 1-2  -alkoxy, C 1-2  -alkoxyethoxy, or with R 3 , a group of formula --CH(CH 3 )CH 2  C(CH 3 ) 2  --, 
     R 3  and R 5  have the significances given above, 
     R 4  &#39; and R 10  &#39; independently signify hydrogen or C 1-2  -alkyl and 
     Y 1  signifies a group of formula --CH 2  CH 2  -- or --CH(CH 3 )CH 2  -- 
     m and z independently signify zero or 1 and 
     n signifies a number from 1 to 5. 
     Particularly preferred disperse dyes correspond to formula Ib ##STR7## wherein D 2  signifies the radical of a diazo component from the series 2,6-dicyano-4-chloro-, -4-bromo-, -4-methyl- or -4-nitrophenyl, 2,4-dinitro-6-chloro-, -6-bromo- or -6-cyanophenyl, 2-chloro- or 2-bromo-4-nitro-6-cyanophenyl, 2,4-dinitrophenyl, 2,6-dichloro- or 2,6-dibromo-4-nitrophenyl, 2-chloro-4-nitro-6-bromophenyl, 2-chloro-, 2-bromo- or 2-cyano-4-nitrophenyl, 2,4-dinitro-5-chlorophenyl or -5-thiocyanophenyl, 2,4-dinitro-5,6-dichlorophenyl, 2,5-dichloro-4-nitrophenyl, 4-nitrophenyl, 4-phenylazophenyl, 4-C 3-4  -alkenyloxycarbonylphenyl, 4-C 3-4  -alkinyloxycarbonylphenyl, 4-C 1-4  -alkoxycarbonylphenyl, 2-C 1-4  -alkoxycarbonyl-4-nitrophenyl, 4-phenoxycarbonylphenyl, 4-benzyloxycarbonylphenyl, 4-(tetrahydrofurfuryl-2&#39;-oxycarbonyl)-phenyl, 3,5-dicyano-4-chloro-thienyl-2, 3,5-dicyano-thienyl-2, 3-cyano-5-nitro-thienyl-2, 3-acetyl-5-nitro-thienyl-2, 3,5-dinitro-thienyl-2, 3-(C 1-4  -alkoxycarbonyl)-5-nitro-thienyl-2, 5-phenylazo-3-cyanothienyl-2, 5-phenylazo-3-cyano-4-methyl-thienyl-2, 5-nitro-thiazolyl-2, 5-nitrobenzisothiazolyl-3, 3-methyl-4-cyano-isothiazolyl-5, 3-phenyl-1,2,4-thiadiazolyl-2, 5-(C 1-2  -alkylmercapto)-1,3,4-thiadiazolyl-2, 3-C 1-2  -alkoxycarbonylethylmercapto-1,2,4-thiadiazolyl-5, 1-cyanomethyl-4,5-dicyano-imidazolyl-2, 6-nitrobenzothiazolyl-2, 5-nitrobenzothiazolyl-2, 6-thiocyanobenzothiazolyl-2, 6-chlorobenzothiazolyl-2, (5),6,(7)-dichlorobenzothiazolyl-2, phthalidyl-5 or of formula ##STR8## in which B signifies oxygen or a group of formula ##STR9## and the symbols R 1  &#39;, R 2  &#39;, R 3 , R 4  &#39;, R 5 , R 10  &#39;, m, n and Y 1  are defined as above. 
     Furthermore, particular preference is given to the disperse dyes of formula Ib, wherein 
     D 2  signifies the radical of a diazo component from the series 2,6-dicyano-4-chloro, -4-bromo, -4-methyl or -4-nitro-phenyl, 2,4-dinitro-6-chloro-, -6-bromo- or -6-cyanophenyl, 2-chloro- or 2-bromo-4-nitro-6-cyanophenyl, 2,4-dinitrophenyl, 2,6-dichloro- or 2,6-dibromo-4-nitrophenyl, 2-chloro-4-nitro-6-bromophenyl, 2-chloro-, 2-bromo- or 2-cyano-4-nitrophenyl, 2,4-dinitro-5-chlorophenyl or -5-thiocyanophenyl, 2,4-dinitro-5,6-dichlorophenyl, 2,5-dichloro-4-nitrophenyl, 4-nitrophenyl, phthalidyl-5, or of formula ##STR10## in which B signifies oxygen or a group of formula ##STR11## and the symbols R 1  &#39;, R 2  &#39;, R 3 , R 4  &#39;, R 5 , R 10  &#39;, m, n and Y 1  are defined as above. 
     Furthermore, particular preference is given to the disperse dyes of formula Ib, wherein 
     D 2  signifies a diazo component from the series 2,4-dinitro-6-chloro-, -6-bromo- or -6-cyanophenyl, 2,4-dinitro-5-chloro- or -5-thiocyanophenyl or 2,4-dinitro-5,6-dichlorophenyl, 
     R 1  &#39; signifies C 1-2  -alkylcarbonylamino, 
     R 2  &#39; signifies C 1-2  -alkoxy or C 1-2  -alkoxyethoxy, 
     R 3  signifies hydrogen, C 1-4  -alkyl, cyanoethyl, C 1-2  -alkoxyethyl, C 3-4  -alkenyl, chlorallyl, C 3-4  -alkinyl, C 1-2  -alkoxycarbonylmethyl, allyloxycarbonylmethyl or propargyloxycarbonylmethyl, 
     R 4  &#39; signifies hydrogen or methyl, 
     R 5  signifies a radical of formula ##STR12## R 10  &#39; signifies hydrogen or methyl, Y 1  signifies a group of formula --CH 2  CH 2  -- or --CH(CH 3 )CH 2  -- 
     m signifies nill or 1, and 
     n signifies a number from 1 to 5. 
     Also preferred are the disperse dyes of formula Ib, wherein 
     D 2  signifies 2,4-dinitro-6-chloro- or -6-bromophenyl, 
     R 1  &#39; signifies C 1-2  -alkylcarbonylamino, 
     R 2  &#39; signifies methoxy or ethoxy, 
     R 3  signifies hydrogen, allyl, chlorallyl or propargyl, 
     R 5  signifies a radical of formula ##STR13## R 10  &#39; signifies hydrogen or methyl, Y 1  signifies 1,2-ethylene, 
     m signifies zero or 1, and 
     n signifies a number from 1 to 5. 
     Further preference is also given to the disperse dyes of formula I, wherein 
     D signifies a diazo component from the series 4-nitrophenyl, 4-nitro-2-ethylsulphonylphenyl, 4-nitro-2-methylsulphonylphenyl, 4-methoxycarbonylphenyl, phthalidyl-5, 4-ethoxycarbonylphenyl, 2-chloro-4-nitrophenyl, 2,6-dichloro-4-nitrophenyl, 2-bromo-4-nitro-6-chlorophenyl or 2-cyano-4-nitrophenyl, 
     K signifies a radical of formula a 
     R 1  signifies hydrogen, methyl, acylamino or chlorine, 
     R 2  signifies hydrogen, 
     R 3  signifies C 1-4  -alkyl, C 3-4  -alkenyl, chlorallyl, benzyl, cyanoethyl, C 1-2  -alkoxyethyl, C 1-4  -alkylcarbonyloxyethyl, C 1-2  -alkoxycarbonylethyl or C 1-4  -alkoxycarbonyloxyethyl, 
     R 4  and R 10  independently signify hydrogen or C 1-2  -alkyl, 
     R 5  signifies a radical of formula ##STR14## Y signifies a group of formula --CH 2  CH 2  -- or --CH(CH 3 )CH 2  -- 
     m and z independently signify zero or 1, and 
     n signifies a number from 1 to 5. 
     One further group of especially preferred disperse dyes corresponds to formula Ib, wherein 
     D 2  signifies a diazo component from the series 4-nitrophenyl, 2-chloro-4-nitrophenyl, 2-bromo-4-nitrophenyl, 2,6-dichloro-4-nitrophenyl, 2-chloro-4-nitro-6-bromophenyl, 2-cyano-4-nitrophenyl, 
     R 1  &#39; signifies hydrogen or methyl, 
     R 2  &#39; signifies hydrogen, 
     R 3  signifies C 1-4  -alkyl, 
     R 4  &#39; signifies hydrogen or methyl, 
     R 5  signifies a radical of formula ##STR15## R 10  &#39; signifies hydrogen, Y 1  signifies 1,2-ethylene, 
     m signifies zero or 1, and 
     n signifies the number 1. 
     The diazo components may be all mono- to bi-nuclear, carbocyclic or heterocyclic organic radicals of aromatic character, which may bear substituents that are conventional in the case of disperse dyes. Water-solubilizing substituents are excluded in particular, that is especially sulphonic acid groups. The diazo components may also be radicals of monoazo compounds. Examples of diazo components are: phenyl, thienyl, thiazolyl, isothiazolyl, thiadiazolyl, pyrazolyl, imidazolyl, triazolyl, benzothiazolyl or benzisothiazolyl radicals, which preferably bear substituents. 
     The substituents on these nuclei may be in particular halogen atoms, especially chlorine, bromine or iodine atoms, nitro, cyano, thiocyano, hydroxyl, alkyl, alkoxy, phenyl, phenoxy and acyl groups, as well as especially also on the thienyl or thiazolyl diazo components, formyl and radicals of formulae --CH═CH--NO 2 , --CH═C(CN) 2  and --CH═C(CN)acyl. 
     Preferred acyl groups correspond to formula E--Y-- or E&#39;--Z--, in which 
     E signifies a hydrocarbon radical which may bear the above-mentioned substituents and/or may contain hetero atoms, preferably an optionally substituted alkyl or phenyl radical, 
     Y signifies a radical --O--CO--, --SO 2  -- or --O--SO 2  --, 
     E&#39; signifies a hydrogen atom or E, 
     Z signifies --CO--, --NE&#34;--CO-- or --NE&#34;--SO 2  -- (E&#34; is only bonded to the nitrogen atom), and 
     E&#34; signifies hydrogen or E. 
     If not otherwise stated, all the said alkyl and alkoxy groups contain 1 to 8, especially 1 to 4 carbon atoms. They may be straight-chain or branched, and bear as substituents e.g. halogen atoms, preferably fluorine or chlorine atoms, hydroxy, alkoxy, phenyl, phenoxy, cyano, thiocyano, acyl, acyloxy or acylamino groups. The intermediate element Y is preferably a group of formula ##STR16## especially --CH 2  CH 2  --. 
     All the said phenyl radicals (also phenoxy and phenylazo radicals) may be further substituted, e.g. by halogen atoms (preferably chlorine or bromine atoms), alkyl, alkoxy, nitro, cyano, thiocyano, acyl, acyloxy or acylamino groups. 
     If not indicated to the contrary, all alkyl, alkylene and alkenyl radicals are straight-chain. 
     Production of the new dyestuffs of formula I is characterized in that a diazotised amine of formula II 
     
         D--NH.sub.2                                                (II) 
    
     is coupled with a compound of formula III ##STR17## 
     Diazotisation and coupling are effected according to generally known methods. 
     The compounds of formulae II and III are known, or may be easily produced from known compounds according to methods known to a person skilled in the art. 
     Dyestuffs of formula I in which D corresponds to the formula ##STR18## where a and/or d are a cyano radical, can also be prepared by cyano-exchange from the corresponding halogen substituted dyestuffs, such a method is known to the skilled person. 
     From an aqueous suspension, the new dyestuffs of formula I are absorbed in an excellent manner on textile material consisting of fully synthetic or semi-synthetic, hydrophobic, high molecular weight organic matter. They are especially suitable for dyeing or printing textile material consisting of linear, aromatic polyesters, as well as cellulose-21/2-acetate and cellulose triacetate. 
     Dyeing or printing are effected in accordance with known processes, e.g. those described in French Patent Specification no. 1.445.371. 
     The dyeings obtained have good all-round fastnesses; apart from the good fastness to thermomigration, also notable are the light fastness, thermofixation fastness and pleating fastness, as well as the excellent wet fastness, following thermal fixation (especially the M&amp;S C4A Co domestic wash). 
     They are also especially suitable for thermo transfer printing processes. 
     In the following examples, the parts and percentages are by weight. The temperatures are given in degrees celsius. 
    
    
     EXAMPLE 1 
     16.3 parts of 2-amino-5-nitrobenzonitrile are stirred into 100 parts of cold sulphuric acid (93%) and mixed at 0° to 5° over the course of 30 minutes with 32 parts of nitrosylsulphuric acid (40%). Stirring continues for 3 to 4 hours at 0° to 5° and then the diazonium salt solution obtained is poured whilst stirring into a mixture of 35.2 parts of 3-(N-methyl-N-phenylamino)-propionic acid-2&#39;-N-phthalimidoethylester, 100 parts of glacial acetic acid, 2 parts of amidosulphonic acid, 200 parts of water and 500 parts of ice. The precipitated dyestuff is filtered off, washed with water until free from acid and dried in a vacuum at 60°. The resultant dyestuff corresponds to formula ##STR19## 
     It dyes polyester fibre material in ruby-red shades with excellent fastness, in particular very good wet fastness after thermal fixing, and is eminently suitable for the modern rapid-dyeing processes, for example the  R  Foron-RD process. 
     λ max . =533 nm (DMF). 
     EXAMPLE 2 
     The process is as described in example 1, but the 35.2 parts of 3-(N-methyl-N-phenylamino)-propionic acid-2&#39;-N-phthalimidoethylester are replaced by 42.4 parts of 3-(N-ethyl-N-phenylamino)-propionic acid-(2&#39;-N-phthalimidoethoxycarbonyl)methylester. The resultant dyestuff corresponds to formula ##STR20## 
     It dyes polyester fibre materials in ruby-red shades with excellent fastnesses, in particular very good wet fastness, after thermal fixing. 
     λ max . =537 nm (DMF). 
     EXAMPLE 3 
     The process is as described in example 1, but the 35.2 parts of 3-(N-methyl-N-phenylamino)-propionic acid-2&#39;-N-phthalimidoethylester are replaced by 38.8 parts of 3-(N-methyl-N-phenylamino)-propionic acid-2&#39;-N-o-sulphobenzimidoethylester. The resultant dyestuff corresponds to formula ##STR21## 
     It dyes polyester fibre materials in ruby-red shades with excellent fastness, in particular very good wet fastness, after thermal fixing, and is eminently suitable for the modern rapid-dyeing processes, for example the  R  Foron-RD process. 
     λ max . =534 nm (DMF). 
     EXAMPLE 4 
     20.7 parts of 1-amino-2,6-dichloro-4-nitrobenzene are stirred into 100 parts of sulphuric acid (93%) and mixed at 30° over the course of one hour with 32 parts of nitrosylsulphuric acid (40%). Stirring is effected for 2-3 hours at 30°-32°, and then the diazonium salt solution obtained is added in drops whilst stirring to a mixture of 35.2 parts of 3-(N-methyl-N-phenylamino)-propionic acid-2&#39;-N-phthalimidoethylester, 100 parts of glacial acetic acid, 2 parts of amidosulphonic acid, 200 parts of water and 500 parts of ice. The precipitated dyestuff is filtered off, washed with water until free from acid, and dried in a vacuum at 60°. It corresponds to formula ##STR22## and dyes polyester fibre material in yellow-brown shades with excellent fastness, in particular very good wet fastness, after thermal fixing. 
     λ max . (DMF)=439 nm. 
     EXAMPLE 5 
     21.8 parts of 2-chloro-4,6-dinitroaniline are stirred into 150 parts of 93% sulphuric acid at 15°-20°, and mixed over the course of 30 minutes with 32 parts of 40% nitrosylsulphuric acid. The mixture is stirred for 2-3 hours in an ice bath, and the diazonium salt solution is continuously poured into a mixture of 46.1 parts of 3-N-(5&#34;-acetylamino-2&#34;-methoxyphenylamino)-propionic acid-2&#39;-N-o-sulphobenzimidoethylester, 100 parts of glacial acetic acid and 300 parts of ice/water. The precipitated dyestuff is filtered off, washed with water until free from acid, and dried in a vacuum at 60°. The dyestuff obtained, with λ max . =598 nm (DMF), corresponds to formula ##STR23## and dyes polyester materials, resp. polyester/cotton mixed fabric, in marine-blue shades with excellent fastness, in particular very good wet fastness, after thermal fixing. 
     EXAMPLE 6 
     20.8 parts of 2-cyano-4,6-dinitroaniline are stirred into 150 parts of sulphuric acid (93%) at 0° to 5° and mixed over the course of 30 minutes with 32 parts of nitrosylsulphuric acid (40%). Stirring continues for 2 to 3 hours at 0° to 5° and then the diazonium salt solution obtained is poured whilst stirring into a mixture of 39.6 parts of 3-[N-methyl-N-(5&#34;-methyl-2&#34;-methoxyphenyl)amino]-propionic acid-2&#39;-N-phthalimidoethylester, 100 parts of glacial acetic acid and 300 parts of ice/water. The precipitated dyestuff is filtered off, washed with water until free from acid and dried in a vacuum at 60°. The resultant dyestuff having a λ max  =613 nm (DMF) corresponds to formula ##STR24## 
     It dyes polyester fibre material in blue shades with excellent fastness, in particular very good wet fastness after thermal fixing, and is eminently suitable for the modern rapid-dyeing processes, for example the  R  Foron-RD process. 
     EXAMPLE 7 
     20.8 parts of 2-cyano4,6-dinitroaniline are stirred into 150 parts of sulphuric acid (93%) at 0° to 5° and mixed over the course of 30 minutes with 32 parts of nitrosylsulphuric acid (40%). Stirring continues for 2 to 3 hours at 0° to 5° and then the diazonium salt solution obtained is poured whilst stirring into a mixture of 45.2 parts of 3-[N-ethyl-N-(3&#39;-methylphenyl)amino]-propionic acid-(3&#34;-N-phthalimido-n-propoxycarbonyl)-methylester, 100 parts of glacial acetic acid, and 300 parts of ice/water. The precipitated dyestuff is filtered off, washed with water until free from acid and dried in a vacuum at 60°. The resultant dyestuff having a λ max  =590 nm (DMF) corresponds to formula ##STR25## 
     It dyes polyester fibre material in ruby-red shades with excellent fastness, in particular very good wet fastness after thermal fixing, and is eminently suitable for the modern rapid-dyeing processes, for example the  R  Foron-RD process. 
     Analogously to the method of Example 1 by using the corresponding starting materials further compounds of formula I may be obtained. 
     These compounds correspond to the formulae given hereinbelow, for which the particular variants are listed in the following tables. They dye polyester fibers in the indicated shades with excellent fastnesses, in particular very good wet fastness after thermal fixing. In the following tables &#34;do.&#34; signifies ditto, i.e. same as the previous entry, PES stands for polyester fibres and DK stands for diazo component radical. 
     The dyestuffs of the following Table I correspond to formula ##STR26## 
     
                                           TABLE 1                                 
__________________________________________________________________________
exp.                                                 Shade                
no.                                                                       
   DK                   R.sub.1 R.sub.2                                   
                                     R.sub.3         on                   
__________________________________________________________________________
                                                     PES                  
 8                                                                        
                        H       H    C.sub.2 H.sub.5 ruby                 
 9 &#34;                    H       H    CH.sub.3        &#34;                    
10 &#34;                    H       H    CH.sub.2 CH.sub.2 CN                 
                                                     red                  
11                                                                        
    ##STR27##           H       H    CH.sub.3        &#34;                    
12                                                                        
    ##STR28##           H       H    C.sub.2 H.sub.4 CN                   
                                                     scarlet              
13                                                                        
    ##STR29##           H       H    &#34;               &#34;                    
14                                                                        
    ##STR30##           NHCOCH.sub.3                                      
                                H    &#34;               red                  
15 &#34;                    &#34;       Cl   H               scarlet              
16                                                                        
    ##STR31##           &#34;       &#34;    H               ruby                 
17                                                                        
    ##STR32##           H       H    CH.sub.3        &#34;                    
18                                                                        
    ##STR33##           H       H    CH.sub.2 CHCH.sub.2                  
                                                     yellow-brown         
19                                                                        
    ##STR34##           H       H    C.sub.4 H.sub.9 &#34;                    
20                                                                        
    ##STR35##           H       H    CH.sub.2 CHCH.sub.2                  
                                                     yellow-brown         
21                                                                        
    ##STR36##           H       H    &#34;               &#34;                    
22                                                                        
    ##STR37##           NHCOCH.sub.3                                      
                                H    C.sub.2 H.sub.5 bluish-violet        
23                                                                        
    ##STR38##           CH.sub.3                                          
                                H    C.sub.4 H.sub.9 reddish blue         
24 &#34;                    NHCOCH.sub.3                                      
                                H    C.sub.3 H.sub.7 blue                 
25 &#34;                    NHCOC.sub.2 H.sub.5                               
                                H    &#34;               &#34;                    
26 &#34;                    NHCOCH.sub.3                                      
                                H    C.sub.2 H.sub.5 /C.sub.3 H.sub.7     
                                     (1:1)           &#34;                    
27                                                                        
    ##STR39##           CH.sub.3                                          
                                H    C.sub.2 H.sub.5 scarlet              
28                                                                        
    ##STR40##           NHCOC.sub.2 H.sub.5                               
                                H    C.sub.2 H.sub.5 bluish red           
29 &#34;                    NHSO.sub.2 CH.sub.3                               
                                H    C.sub.2 H.sub.5 /C.sub.3 H.sub.7     
                                     (1:1)           red                  
30                                                                        
    ##STR41##           NHCOC.sub.2 H.sub.5                               
                                H    &#34;               ruby                 
31                                                                        
    ##STR42##           CH.sub.3                                          
                                H    C.sub.4 H.sub.9 bluish violet        
32                                                                        
    ##STR43##           H       H    CH.sub.3        bluish red           
33 &#34;                    CH.sub.3                                          
                                H    C.sub.2 H.sub.5 violet               
34                                                                        
    ##STR44##           NHCOCH.sub.3                                      
                                H    C.sub.2 H.sub.4 CN                   
                                                     bluish red           
35                                                                        
    ##STR45##           CH.sub.3                                          
                                H    C.sub.2 H.sub.5 scarlet              
36 &#34;                    NHCOC.sub.2 H.sub.5                               
                                H    &#34;               red                  
37                                                                        
    ##STR46##           H       H    C.sub.2 H.sub.5 scarlet              
38 &#34;                    CH.sub.3                                          
                                H    &#34;               red                  
39 &#34;                    NHCOCH.sub.3                                      
                                H    &#34;               ruby                 
40 &#34;                    &#34;       H    C.sub.2 H.sub.4 CN                   
                                                     red                  
41                                                                        
    ##STR47##           CH.sub.3                                          
                                H    C.sub.4 H.sub.9 bluish red           
42                                                                        
    ##STR48##           &#34;       H    C.sub.2 H.sub.5 dark blue            
43                                                                        
    ##STR49##           NHCOCH.sub.3                                      
                                H    C.sub.2 H.sub.5 /C.sub.3 H.sub.7     
                                     (1:1)           greenish blue        
44                                                                        
    ##STR50##           H       H    C.sub.2 H.sub.5 blue                 
45 &#34;                    CH.sub.3                                          
                                H    &#34;               greenish blue        
46 &#34;                    H       H    C.sub.2 H.sub.4 OCOCH.sub.3          
                                                     reddish blue         
47 &#34;                    NHCOCH.sub.3                                      
                                H    C.sub.2 H.sub.5 bluish green         
48                                                                        
    ##STR51##           CH.sub.3                                          
                                H    C.sub.4 H.sub.9 reddish blue         
49                                                                        
    ##STR52##           &#34;       H    C.sub.2 H.sub.5 reddish navy blue    
50                                                                        
    ##STR53##           H       H    &#34;               dark blue            
51                                                                        
    ##STR54##           H       H    C.sub.2 H.sub.5 dark blue            
52                                                                        
    ##STR55##           H       H    C.sub.2 H.sub.5 greenish navy blue   
53                                                                        
    ##STR56##           NHCOCH.sub.3                                      
                                H                                         
                                      ##STR57##      red                  
54 &#34;                    &#34;       H    C.sub.2 H.sub.5 bluish red           
55                                                                        
    ##STR58##           H       H    C.sub.2 H.sub.5 violet               
56                                                                        
    ##STR59##           H       H    C.sub.2 H.sub.4 CN                   
                                                     red                  
57                                                                        
    ##STR60##           CH.sub.3                                          
                                H    C.sub.2 H.sub.5 violet               
58                                                                        
    ##STR61##           &#34;       H    CH.sub.3        violet               
59                                                                        
    ##STR62##           CH.sub.3                                          
                                H    &#34;               ruby                 
60 &#34;                    H       H    C.sub.2 H.sub.5 red                  
61                                                                        
    ##STR63##           NHCOC.sub.2 H.sub.5                               
                                H    &#34;               blue                 
62 &#34;                    NHCOCH.sub.3                                      
                                H    &#34;               &#34;                    
63 &#34;                    &#34;       H    C.sub.2 H.sub.5 /C.sub.3 H.sub.7     
                                     (1:1)           &#34;                    
64                                                                        
    ##STR64##           CH.sub.3                                          
                                OCH.sub.3                                 
                                     CH.sub.3        bluish violet        
65                                                                        
    ##STR65##           NHCOCH.sub.3                                      
                                H    C.sub.2 H.sub.5 &#34;                    
66                                                                        
    ##STR66##           NHCOCH.sub.3                                      
                                H    C.sub.2 H.sub.5 red                  
67                                                                        
    ##STR67##           H       H    CH.sub.3        yellow               
68 &#34;                    H       H    C.sub.2 H.sub.5 &#34;                    
69                                                                        
    ##STR68##           H       H    CH.sub.3        &#34;                    
70 &#34;                    CH.sub.3                                          
                                H    &#34;               &#34;                    
71                                                                        
    ##STR69##           &#34;       H    &#34;               &#34;                    
72 &#34;                    H       H    &#34;               &#34;                    
73                                                                        
    ##STR70##           H       H    &#34;               orange               
74 &#34;                    H       H    C.sub.2 H.sub.5 &#34;                    
75                                                                        
    ##STR71##           H       H    CH.sub.2 CH.sub.2 OCOOCH.sub.3       
                                                     orange               
76 &#34;                    CH.sub.3                                          
                                H    CH.sub.3        red                  
77                                                                        
    ##STR72##           H       H    &#34;               &#34;                    
78                                                                        
    ##STR73##           H       H    CH.sub.2 CHCH.sub.2                  
                                                     &#34;                    
79                                                                        
    ##STR74##           H       H    CH.sub.2 CH.sub.2 OCOCH.sub.3        
                                                     ruby                 
80 &#34;                    H       H    CH.sub.2 CH.sub.2 OCOOCH.sub.3       
                                                     &#34;                    
81                                                                        
    ##STR75##           H       H    C.sub.2 H.sub.5 &#34;                    
82                                                                        
    ##STR76##           H       H    C.sub.2 H.sub.5 ruby                 
83                                                                        
    ##STR77##           H       H    &#34;               yellow-brown         
__________________________________________________________________________
 
    
     The dyestuffs of the following Table 2 correspond to the formula 
     
                                           TABLE 2                                 
__________________________________________________________________________
 ##STR78##                                                                
                                                    Shade                 
exp. no.                                                                  
     DK                   R.sub.1 R.sub.2                                 
                                     R.sub.3        on PES                
__________________________________________________________________________
84                                                                        
      ##STR79##           H       H  C.sub.2 H.sub.5                      
                                                    ruby                  
85                                                                        
      ##STR80##           H       H  C.sub.4 H.sub.9                      
                                                    &#34;                     
86   &#34;                    H       H  CH.sub.2 CH.sub.2 CN                 
                                                    red                   
87                                                                        
      ##STR81##           H       H  CH.sub.3       &#34;                     
88                                                                        
      ##STR82##           H       H  C.sub.2 H.sub.4 CN                   
                                                    scarlet               
89                                                                        
      ##STR83##           H       H  C.sub.2 H.sub.4 CN                   
                                                    scarlet               
90                                                                        
      ##STR84##           NHCOCH.sub.3                                    
                                  H  &#34;              red                   
91   &#34;                    &#34;       Cl H              scarlet               
92                                                                        
      ##STR85##           &#34;       &#34;  H              ruby                  
93                                                                        
      ##STR86##           H       H  C.sub.2 H.sub.5                      
                                                    &#34;                     
94                                                                        
      ##STR87##           H       H  CH.sub.2 CHCH.sub.2                  
                                                    yellow-brown          
95                                                                        
      ##STR88##           H       H  C.sub.4 H.sub.9                      
                                                    yellow-brown          
96                                                                        
      ##STR89##           H       H  CH.sub.2 CHCH.sub.2                  
                                                    &#34;                     
97                                                                        
      ##STR90##           H       H  &#34;              &#34;                     
98                                                                        
      ##STR91##           NHCOCH.sub.3                                    
                                  H  C.sub.2 H.sub.5                      
                                                    bluish violet         
99                                                                        
      ##STR92##           CH.sub.3                                        
                                  H  C.sub.4 H.sub.9                      
                                                    reddish blue          
100                                                                       
      ##STR93##           NHCOCH.sub.3                                    
                                  H  C.sub.3 H.sub.7                      
                                                    blue                  
101  &#34;                    NHCOC.sub.2 H.sub.5                             
                                  &#34;  &#34;                                    
102  &#34;                    NHCOCH.sub.3                                    
                                  H  C.sub.2 H.sub.5 /C.sub.3 H.sub.7     
                                     (1:1)          &#34;                     
103                                                                       
      ##STR94##           CH.sub.3                                        
                                  H  C.sub.2 H.sub.5                      
                                                    scarlet               
104                                                                       
      ##STR95##           NHCOC.sub.2 H.sub.5                             
                                  H  C.sub.2 H.sub.5                      
                                                    bluish red            
105  &#34;                    NHSO.sub.2 CH.sub.3                             
                                  H  C.sub.2 H.sub.5 /C.sub.3 H.sub.7     
                                     (1:1)          red                   
106                                                                       
      ##STR96##           NHCOC.sub.2 H.sub.5                             
                                  H  &#34;              ruby                  
107                                                                       
      ##STR97##           CH.sub.3                                        
                                  H  C.sub.4 H.sub.9                      
                                                    bluish violet         
108                                                                       
      ##STR98##           H       H  CH.sub.3       bluish red            
109  &#34;                    CH.sub.3                                        
                                  H  C.sub.2 H.sub.5                      
                                                    violet                
110  &#34;                    NHCOCH.sub.3                                    
                                  H  C.sub.2 H.sub.4 CN                   
                                                    bluish red            
111                                                                       
      ##STR99##           CH.sub.3                                        
                                  H  C.sub.2 H.sub.5                      
                                                    scarlet               
112  &#34;                    NHCOC.sub.2 H.sub.5                             
                                  H  &#34;              red                   
113                                                                       
      ##STR100##          H       H  C.sub.2 H.sub.5                      
                                                    scarlet               
114  &#34;                    CH.sub.3                                        
                                  H  &#34;              red                   
115  &#34;                    NHCOCH.sub.3                                    
                                  H  &#34;              ruby                  
116  &#34;                    &#34;       H  C.sub.2 H.sub.4 CN                   
                                                    red                   
117                                                                       
      ##STR101##          CH.sub.3                                        
                                  H  C.sub.4 H.sub.9                      
                                                    bluish red            
118                                                                       
      ##STR102##          CH.sub.3                                        
                                  H  C.sub.2 H.sub.5                      
                                                    dark blue             
119  &#34;                    NHCOCH.sub.3                                    
                                  H  C.sub.2 H.sub.5 /C.sub.3 H.sub.7     
                                     (1:1)          greenish blue         
120                                                                       
      ##STR103##          H       H  C.sub.2 H.sub.5                      
                                                    blue                  
121  &#34;                    CH.sub.3                                        
                                  H  &#34;              greenish blue         
122  &#34;                    H       H  C.sub.2 H.sub.4 OCOCH.sub.3          
                                                    reddish blue          
123  &#34;                    NHCOCH.sub.3                                    
                                  H  C.sub.2 H.sub.5                      
                                                    bluish green          
124                                                                       
      ##STR104##          CH.sub.3                                        
                                  H  C.sub.4 H.sub.9                      
                                                    reddish blue          
125                                                                       
      ##STR105##          &#34;       H  C.sub.2 H.sub.5                      
                                                    reddish navy blue     
126                                                                       
      ##STR106##          H       H  &#34;              dark blue             
127                                                                       
      ##STR107##          H       H  C.sub.2 H.sub.5                      
                                                    dark blue             
128                                                                       
      ##STR108##          H       H  C.sub.2 H.sub.5                      
                                                    greenish navy blue    
129                                                                       
      ##STR109##          NHCOCH.sub.3                                    
                                  H                                       
                                      ##STR110##    red                   
130  &#34;                    &#34;       H  C.sub.2 H.sub.5                      
                                                    bluish red            
131                                                                       
      ##STR111##          H       H  C.sub.2 H.sub.5                      
                                                    violet                
132                                                                       
      ##STR112##          H       H  C.sub.2 H.sub.4 CN                   
                                                    red                   
133                                                                       
      ##STR113##          CH.sub.3                                        
                                  H  C.sub.2 H.sub.5                      
                                                    violet                
134                                                                       
      ##STR114##          CH.sub.3                                        
                                  H  CH.sub.3       violet                
135                                                                       
      ##STR115##          CH      H  &#34;              ruby                  
136  &#34;                    H       H  C.sub.2 H.sub.5                      
                                                    red                   
137                                                                       
      ##STR116##          NHCOC.sub.2 H.sub.5                             
                                  H  &#34;              blue                  
138                                                                       
      ##STR117##          NHCOCH.sub.3                                    
                                  H  &#34;              &#34;                     
139  &#34;                    &#34;       H  C.sub.2 H.sub.5 /C.sub.3 H.sub.7     
                                     (1:1)          &#34;                     
140                                                                       
      ##STR118##          &#34;       H  &#34;              bluish violet         
141                                                                       
      ##STR119##          NHCOCH.sub.3                                    
                                  H  C.sub.2 H.sub.5                      
                                                    bluish violet         
142                                                                       
      ##STR120##          &#34;       H  &#34;              red                   
143                                                                       
      ##STR121##          H       H  CH.sub.3       yellow                
144  &#34;                    H       H  C.sub.2 H.sub.5                      
                                                    &#34;                     
145                                                                       
      ##STR122##          H       H  CH.sub.3       &#34;                     
146  &#34;                    CH.sub.3                                        
                                  H  &#34;              &#34;                     
147                                                                       
      ##STR123##          H       H  &#34;              &#34;                     
148  &#34;                    H       H  &#34;              &#34;                     
149                                                                       
      ##STR124##          H       H  CH.sub.3       orange                
150  &#34;                    H       H  C.sub.2 H.sub.5                      
                                                    &#34;                     
151  &#34;                    H       H  CH.sub.2 CH.sub.2 OCOOCH.sub.3       
                                                    &#34;                     
152  &#34;                    CH.sub.3                                        
                                  H  CH.sub.3       red                   
153                                                                       
      ##STR125##          H       H  &#34;              &#34;                     
154                                                                       
      ##STR126##          H       H  CH.sub.2 CHCH.sub.2                  
                                                    &#34;                     
155                                                                       
      ##STR127##          H       H  CH.sub.2 CH.sub.2 OCOCH.sub.3        
                                                    ruby                  
156  &#34;                    H       H  CH.sub.2 CH.sub.2 OCOOCH.sub.3       
                                                    &#34;                     
157                                                                       
      ##STR128##          H       H  CH.sub.3       ruby                  
158                                                                       
      ##STR129##          H       H  &#34;              &#34;                     
159                                                                       
      ##STR130##          H       H  &#34;              yellow brown          
160  &#34;                    H       H  CH.sub.3       &#34;                     
__________________________________________________________________________
 
    
     The dyestuffs of the following Table 3 correspond to formula 
     
                                           TABLE 3                                 
__________________________________________________________________________
 ##STR131##                                                               
exp.                                                Shade                 
no.                                                                       
   DK                   R.sub.1  R.sub.2                                  
                                     R.sub.3        on PES                
__________________________________________________________________________
161                                                                       
    ##STR132##          H        H   CH.sub.3       ruby                  
162                                                                       
    ##STR133##          H        H   C.sub.4 H.sub.9                      
                                                    &#34;                     
163                                                                       
   &#34;                    H        H   CH.sub.2 CH.sub.2 CN                 
                                                    red                   
164                                                                       
    ##STR134##          H        H   CH.sub.3       &#34;                     
165                                                                       
    ##STR135##          H        H   C.sub.2 H.sub.4 CN                   
                                                    scarlet               
166                                                                       
    ##STR136##          H        H   C.sub.2 H.sub.4 CN                   
                                                    scarlet               
167                                                                       
    ##STR137##          NHCOCH.sub.3                                      
                                 H   &#34;              red                   
168                                                                       
   &#34;                    &#34;        Cl  H              scarlet               
169                                                                       
    ##STR138##          &#34;        &#34;   H              ruby                  
170                                                                       
    ##STR139##          H        H   CH.sub.3       &#34;                     
171                                                                       
    ##STR140##          H        H   CH.sub.2 CHCH.sub.2                  
                                                    yellow-brown          
172                                                                       
    ##STR141##          H        H   C.sub.4 H.sub.9                      
                                                    yellow-brown          
173                                                                       
    ##STR142##          H        H   CH.sub.2 CHCH.sub.2                  
                                                    &#34;                     
174                                                                       
    ##STR143##          H        H   &#34;              &#34;                     
175                                                                       
    ##STR144##          NHCOCH.sub.3                                      
                                 H   C.sub.2 H.sub.5                      
                                                    bluish violet         
176                                                                       
    ##STR145##          CH.sub.3 H   C.sub.4 H.sub.9                      
                                                    reddish blue          
177                                                                       
    ##STR146##          NHCOCH.sub.3                                      
                                 H   C.sub.3 H.sub.7                      
                                                    blue                  
178                                                                       
   &#34;                    NHCOC.sub.2 H.sub.5                               
                                 H   &#34;              &#34;                     
179                                                                       
   &#34;                    NHCOCH.sub.3                                      
                                 H   C.sub.2 H.sub.5 /C.sub.3 H.sub.7     
                                     (1:1)          &#34;                     
180                                                                       
    ##STR147##          CH.sub.3 H   C.sub.2 H.sub.5                      
                                                    scarlet               
181                                                                       
   &#34;                    NHCOC.sub.2 H.sub.5                               
                                 H   &#34;              bluish red            
182                                                                       
   &#34;                    NHSO.sub.2 CH.sub.3                               
                                 H   C.sub.2 H.sub.5 /C.sub.3 H.sub.7     
                                     (1:1)          red                   
183                                                                       
    ##STR148##          NHCOC.sub.2 H.sub.5                               
                                 H   &#34;              ruby                  
184                                                                       
    ##STR149##          CH.sub.3 H   C.sub.4 H.sub.9                      
                                                    bluish violet         
185                                                                       
    ##STR150##          H        H   CH.sub.3       bluish red            
186                                                                       
   &#34;                    CH.sub.3 H   C.sub.2 H.sub.5                      
                                                    violet                
187                                                                       
   &#34;                    NHCOCH.sub.3                                      
                                 H   C.sub.2 H.sub.4 CN                   
                                                    bluish red            
188                                                                       
    ##STR151##          CH.sub.3 H   C.sub.2 H.sub.5                      
                                                    scarlet               
189                                                                       
   &#34;                    NHCOC.sub.2 H.sub.5                               
                                 H   &#34;              red                   
190                                                                       
    ##STR152##          H        H   C.sub.2 H.sub.5                      
                                                    scarlet               
191                                                                       
   &#34;                    CH.sub.3 H   &#34;              red                   
192                                                                       
   &#34;                    NHCOCH.sub.3                                      
                                 H   &#34;              ruby                  
193                                                                       
   &#34;                    &#34;        H   C.sub.2 H.sub.4 CN                   
                                                    red                   
194                                                                       
    ##STR153##          CH.sub.3 H   C.sub.4 H.sub.9                      
                                                    bluish red            
195                                                                       
    ##STR154##          CH.sub.3 H   C.sub.2 H.sub.5                      
                                                    dark blue             
196                                                                       
   &#34;                    NHCOCH.sub.3                                      
                                 H   C.sub.2 H.sub.5 /C.sub.3 H.sub.7     
                                     (1:1)          greenish blue         
197                                                                       
    ##STR155##          H        H   C.sub.2 H.sub.5                      
                                                    blue                  
198                                                                       
   &#34;                    CH.sub.3 H   &#34;              greenish blue         
199                                                                       
   &#34;                    H        H   C.sub.2 H.sub.4 OCOCH.sub.3          
                                                    reddish blue          
200                                                                       
   &#34;                    NHCOCH.sub.3                                      
                                 H   C.sub.2 H.sub.5                      
                                                    bluish green          
201                                                                       
    ##STR156##          CH.sub.3 H   C.sub.4 H.sub.9                      
                                                    reddish blue          
202                                                                       
    ##STR157##          &#34;        H   C.sub.2 H.sub.5                      
                                                    reddish navy blue     
203                                                                       
    ##STR158##          H        H   &#34;              dark blue             
204                                                                       
    ##STR159##          H        H   C.sub.2 H.sub.5                      
                                                    dark blue             
205                                                                       
    ##STR160##          H        H   C.sub.2 H.sub.5                      
                                                    greenish navy blue    
206                                                                       
    ##STR161##          NHCOCH.sub.3                                      
                                 H                                        
                                      ##STR162##    red                   
207                                                                       
   &#34;                    &#34;        H   C.sub.2 H.sub.5                      
                                                    bluish red            
208                                                                       
    ##STR163##          H        H   C.sub.2 H.sub.5                      
                                                    violet                
209                                                                       
    ##STR164##          H        H   C.sub.2 H.sub.4 CN                   
                                                    red                   
210                                                                       
    ##STR165##          CH.sub.3 H   C.sub.2 H.sub.5                      
                                                    violet                
211                                                                       
    ##STR166##          CH.sub.3 H   CH.sub.3       violet                
212                                                                       
    ##STR167##          CH.sub.3 H   &#34;              ruby                  
213                                                                       
   &#34;                    H        H   C.sub.2 H.sub.5                      
                                                    red                   
214                                                                       
    ##STR168##          NHCOC.sub.2 H.sub.5                               
                                 H   &#34;              blue                  
215                                                                       
   &#34;                    NHCOCH.sub.3                                      
                                 H   &#34;              &#34;                     
216                                                                       
   &#34;                    &#34;        H   C.sub.2 H.sub.5 /C.sub.3 H.sub.7     
                                     (1:1)          &#34;                     
217                                                                       
    ##STR169##          &#34;        H   &#34;              bluish violet         
218                                                                       
    ##STR170##          NHCOCH.sub.3                                      
                                 H   C.sub.2 H.sub.5                      
                                                    bluish violet         
219                                                                       
    ##STR171##          &#34;        H   &#34;              red                   
220                                                                       
    ##STR172##          H        H   CH.sub.3       yellow                
221                                                                       
   &#34;                    H        H   C.sub.2 H.sub.5                      
                                                    &#34;                     
222                                                                       
    ##STR173##          H        H   CH.sub.3       &#34;                     
223                                                                       
   &#34;                    CH.sub.3 H   &#34;              &#34;                     
224                                                                       
    ##STR174##          &#34;        H   &#34;              &#34;                     
225                                                                       
   &#34;                    H        H   &#34;              &#34;                     
226                                                                       
    ##STR175##          H        H   &#34;              orange                
227                                                                       
   &#34;                    H        H   C.sub.2 H.sub.5                      
                                                    &#34;                     
228                                                                       
   &#34;                    H        H   CH.sub.2 CH.sub.2 OCOOCH.sub.3       
                                                    &#34;                     
229                                                                       
   &#34;                    CH.sub.3 H   CH.sub.3       red                   
230                                                                       
    ##STR176##          H        H   &#34;              &#34;                     
231                                                                       
    ##STR177##          H        H   CH.sub.2 CHCH.sub.2                  
                                                    &#34;                     
232                                                                       
    ##STR178##          H        H   CH.sub.2 CH.sub.2 OCOCH.sub.3        
                                                    ruby                  
233                                                                       
   &#34;                    H        H   CH.sub.2 CH.sub.2 OCOOCH.sub.3       
                                                    &#34;                     
234                                                                       
    ##STR179##          H        H   C.sub.2 H.sub.5                      
                                                    ruby                  
235                                                                       
    ##STR180##          H        H   C.sub.3 H.sub.7                      
                                                    &#34;                     
236                                                                       
    ##STR181##          H        H   &#34;              yellow-brown          
237                                                                       
   &#34;                    H        H   CH.sub.3       &#34;                     
__________________________________________________________________________
 
    
     The dyestuffs of the following Table 4 correspond to formula 
     
                                           TABLE 4                                 
__________________________________________________________________________
 ##STR182##                                                               
exp.                                                Shade                 
no.                                                                       
   DK                   R.sub.1 R.sub.2                                   
                                     R.sub.3        on PES                
__________________________________________________________________________
238                                                                       
    ##STR183##          H       H    C.sub.2 H.sub.5                      
                                                    ruby                  
239                                                                       
    ##STR184##          H       H    CH.sub.3       &#34;                     
240                                                                       
   &#34;                    H       H    CH.sub.2 CH.sub.2 CN                 
                                                    red                   
241                                                                       
    ##STR185##          H       H    CH.sub.3       &#34;                     
242                                                                       
    ##STR186##          H       H    C.sub.2 H.sub.4 CN                   
                                                    scarlet               
243                                                                       
    ##STR187##          H       H    C.sub.2 H.sub.4 CN                   
                                                    scarlet               
244                                                                       
    ##STR188##          NHCOCH.sub.3                                      
                                H    &#34;              red                   
245                                                                       
   &#34;                    &#34;       Cl   H              scarlet               
246                                                                       
    ##STR189##          &#34;       &#34;    H              ruby                  
247                                                                       
    ##STR190##          H       H    CH.sub.3       &#34;                     
248                                                                       
    ##STR191##          H       H    CH.sub.2 CHCH.sub.2                  
                                                    yellow-brown          
249                                                                       
    ##STR192##          H       H    C.sub.4 H.sub.9                      
                                                    yellow-brown          
250                                                                       
    ##STR193##          H       H    CH.sub.2 CHCH.sub.2                  
                                                    &#34;                     
251                                                                       
    ##STR194##          H       H    &#34;              &#34;                     
252                                                                       
    ##STR195##          NHCOCH.sub.3                                      
                                H    C.sub.2 H.sub.5                      
                                                    bluish violet         
253                                                                       
    ##STR196##          CH.sub.3                                          
                                H    C.sub.4 H.sub.9                      
                                                    reddish blue          
254                                                                       
    ##STR197##          NHCOCH.sub.3                                      
                                H    C.sub.3 H.sub.7                      
                                                    blue                  
255                                                                       
   &#34;                    NHCOC.sub.2 H.sub.5                               
                                H    &#34;              &#34;                     
256                                                                       
   &#34;                    NHCOCH.sub.3                                      
                                H    C.sub.2 H.sub.5 /C.sub.3 H.sub.7     
                                     (1:1)          &#34;                     
257                                                                       
    ##STR198##          CH.sub.3                                          
                                H    C.sub.2 H.sub.5                      
                                                    scarlet               
258                                                                       
   &#34;                    NHCOC.sub.2 H.sub.5                               
                                H    &#34;              bluish red            
259                                                                       
   &#34;                    NHSO.sub.2 CH.sub.3                               
                                H    C.sub.2 H.sub.5 /C.sub.3 H.sub.7     
                                     (1:1)          red                   
260                                                                       
    ##STR199##          NHCOC.sub.2 H.sub.5                               
                                H    &#34;              ruby                  
261                                                                       
    ##STR200##          CH.sub.3                                          
                                H    C.sub.4 H.sub.9                      
                                                    bluish violet         
262                                                                       
    ##STR201##          H       H    CH.sub.3       bluish red            
263                                                                       
   &#34;                    CH.sub.3                                          
                                H    C.sub.2 H.sub.5                      
                                                    violet                
264                                                                       
   &#34;                    NHCOCH.sub.3                                      
                                H    C.sub.2 H.sub.4 CN                   
                                                    bluish red            
265                                                                       
    ##STR202##          CH.sub.3                                          
                                H    C.sub.2 H.sub.5                      
                                                    scarlet               
266                                                                       
   &#34;                    NHCOC.sub.2 H.sub.5                               
                                H    &#34;              red                   
267                                                                       
    ##STR203##          H       H    C.sub.2 H.sub.5                      
                                                    scarlet               
268                                                                       
   &#34;                    CH.sub.3                                          
                                H    &#34;              red                   
269                                                                       
   &#34;                    NHCOCH.sub.3                                      
                                H    &#34;              ruby                  
270                                                                       
   &#34;                    &#34;       H    C.sub.2 H.sub.4 CN                   
                                                    red                   
271                                                                       
    ##STR204##          CH.sub.3                                          
                                H    C.sub.4 H.sub.9                      
                                                    bluish red            
272                                                                       
    ##STR205##          &#34;       H    C.sub.2 H.sub.5                      
                                                    dark blue             
273                                                                       
   &#34;                    NHCOCH.sub.3                                      
                                H    C.sub.2 H.sub.5 /C.sub.3 H.sub.7     
                                     (1:1)          greenish blue         
274                                                                       
    ##STR206##          H       H    C.sub.2 H.sub.5                      
                                                    blue                  
275                                                                       
   &#34;                    CH.sub.3                                          
                                H    &#34;              greenish blue         
276                                                                       
   &#34;                    H       H    C.sub.2 H.sub.4 OCOCH.sub.3          
                                                    reddish blue          
277                                                                       
   &#34;                    NHCOCH.sub.3                                      
                                H    C.sub.2 H.sub.5                      
                                                    bluish green          
278                                                                       
    ##STR207##          CH.sub.3                                          
                                H    C.sub.4 H.sub.9                      
                                                    reddish blue          
279                                                                       
    ##STR208##          CH.sub.3                                          
                                H    C.sub.2 H.sub.5                      
                                                    reddish navy blue     
280                                                                       
    ##STR209##          H       H    &#34;              dark blue             
281                                                                       
    ##STR210##          H       H    &#34;              &#34;                     
282                                                                       
    ##STR211##          H       H    C.sub.2 H.sub.5                      
                                                    greenish navy blue    
283                                                                       
    ##STR212##          NHCOCH.sub.3                                      
                                H                                         
                                      ##STR213##    red                   
284                                                                       
   &#34;                    &#34;       H    C.sub.2 H.sub.5                      
                                                    bluish red            
285                                                                       
    ##STR214##          H       H    C.sub.2 H.sub.5                      
                                                    violet                
286                                                                       
    ##STR215##          H       H    C.sub.2 H.sub.4 CN                   
                                                    red                   
287                                                                       
    ##STR216##          CH.sub.3                                          
                                H    C.sub.2 H.sub.5                      
                                                    violet                
288                                                                       
   &#34;                    &#34;       H    CH.sub.3       violet                
289                                                                       
    ##STR217##          CH.sub.3                                          
                                H    &#34;              ruby                  
290                                                                       
   &#34;                    H       H    C.sub.2 H.sub.5                      
                                                    red                   
291                                                                       
    ##STR218##          CH.sub.3                                          
                                OCH.sub.3                                 
                                     CH.sub.3       blue                  
292                                                                       
   &#34;                    NHCOCH.sub.3                                      
                                H    &#34;              &#34;                     
293                                                                       
   &#34;                    &#34;       H    C.sub.2 H.sub.5 /C.sub.3 H.sub.7     
                                     (1:1)          &#34;                     
294                                                                       
    ##STR219##          NHCOCH.sub.3                                      
                                H    C.sub.2 H.sub.5 /C.sub.3 H.sub.7     
                                     (1:1)          bluish violet         
295                                                                       
    ##STR220##          &#34;       H    C.sub.2 H.sub.5                      
                                                    &#34;                     
296                                                                       
    ##STR221##          &#34;       H    &#34;              red                   
297                                                                       
    ##STR222##          H       H    CH.sub.3       yellow                
298                                                                       
   &#34;                    H       H    C.sub.2 H.sub.5                      
                                                    &#34;                     
299                                                                       
    ##STR223##          H       H    CH.sub.3       &#34;                     
300                                                                       
   &#34;                    CH.sub.3                                          
                                H    &#34;              &#34;                     
301                                                                       
    ##STR224##          CH.sub.3                                          
                                H    CH.sub.3       yellow                
302                                                                       
   &#34;                    H       H    &#34;              &#34;                     
303                                                                       
    ##STR225##          H       H    &#34;              orange                
304                                                                       
   &#34;                    H       H    C.sub.2 H.sub.5                      
                                                    &#34;                     
305                                                                       
   &#34;                    H       H    CH.sub.2 CH.sub.2 OCOOCH.sub.3       
                                                    &#34;                     
306                                                                       
   &#34;                    CH.sub.3                                          
                                H    CH.sub.3       red                   
307                                                                       
    ##STR226##          H       H    &#34;              &#34;                     
308                                                                       
    ##STR227##          H       H    CH.sub.2 CHCH.sub.2                  
                                                    &#34;                     
309                                                                       
    ##STR228##          H       H    CH.sub.2 CH.sub.2 OCOCH.sub.3        
                                                    ruby                  
310                                                                       
    ##STR229##          H       H    CH.sub.2 CH.sub.2 OCOOCH.sub.3       
                                                    ruby                  
311                                                                       
    ##STR230##          H       H    C.sub.2 H.sub.5                      
                                                    &#34;                     
312                                                                       
    ##STR231##          H       H    &#34;              &#34;                     
313                                                                       
    ##STR232##          H       H    &#34;              yellow-brown          
314                                                                       
   &#34;                    H       H    CH.sub.3       &#34;                     
__________________________________________________________________________
 
    
     
                                           TABLE 5                                 
__________________________________________________________________________
The dyestuffs of the following Table 5 correspond to the formula          
 ##STR233##                                                               
exp. no.                                                                  
      R.sub.11                                                            
           R.sub.12                                                       
               R.sub.3        R.sub.4                                     
                                    R.sub.10                              
                                         Shade on PES                     
__________________________________________________________________________
315   Cl   Cl  CH.sub.3       H     CH.sub.3                              
                                         yellow-brown                     
316   Cl   Cl  &#34;              CH.sub.3                                    
                                    H    &#34;                                
317   Br   Br  &#34;              H     CH.sub.3                              
                                         &#34;                                
318   CN   H   CH.sub.2 C.sub.6 H.sub.5                                   
                              CH.sub.3                                    
                                    H    ruby-red                         
319   &#34;    H   CH.sub.2 CH.sub.2 C.sub.6 H.sub.5                          
                              H     CH.sub.3                              
                                         &#34;                                
320   &#34;    H   CH.sub.2 CH.sub.2 OC.sub.6 H.sub.5                         
                              CH.sub.3                                    
                                    H    &#34;                                
321   &#34;    H   CH.sub.2 CH.sub.2 OCOOCH.sub.3                             
                              H     CH.sub.3                              
                                         bluish red                       
322   &#34;    H   CH.sub.2 CHCH.sub.2                                        
                              H     &#34;    &#34;                                
323   Cl   Cl  CH.sub.2 CH.sub.3                                          
                              H     &#34;    yellow-brown                     
324   CN   H                                                              
                ##STR234##    CH.sub.3                                    
                                    H    ruby-red                         
325   &#34;    H   CH.sub.3       H     CH.sub.3                              
                                         &#34;                                
326   &#34;    H   CH.sub.2 CH.sub.2 OCOOC.sub.2 H.sub.5                      
                              H     &#34;    &#34;                                
327   Br   Cl  CH.sub.3       H     &#34;    yellow-brown                     
__________________________________________________________________________
 
    
     
                                           TABLE 6                                 
__________________________________________________________________________
The dyestuffs of the following Table 6 correspond to the formula          
 ##STR235##                                                               
exp. no.                                                                  
      R.sub.11                                                            
           R.sub.12                                                       
               R.sub.3        R.sub.4                                     
                                    R.sub.10                              
                                         Shade on PES                     
__________________________________________________________________________
328   Cl   Cl  CH.sub.3       H     CH.sub.3                              
                                         yellow-brown                     
329   Cl   Cl  &#34;              CH.sub.3                                    
                                    H    &#34;                                
330   Br   Br  &#34;              H     CH.sub.3                              
                                         &#34;                                
331   CN   H   CH.sub.2 C.sub.6 H.sub.5                                   
                              CH.sub.3                                    
                                    H    ruby-red                         
332   &#34;    H   CH.sub.2 CH.sub.2 C.sub.6 H.sub.5                          
                              H     CH.sub.3                              
                                         &#34;                                
333   &#34;    H   CH.sub.2 CH.sub.2 OC.sub.6 H.sub.5                         
                              CH.sub.3                                    
                                    H    &#34;                                
334   &#34;    H   CH.sub.2 CH.sub.2 OCOOCH.sub.3                             
                              H     CH.sub.3                              
                                         bluish red                       
335   &#34;    H   CH.sub.2 CHCH.sub.2                                        
                              H     &#34;    &#34;                                
336   Cl   Cl  CH.sub.2 CH.sub.3                                          
                              H     &#34;    yellow-brown                     
337   CN   H                                                              
                ##STR236##    CH.sub.3                                    
                                    H    ruby-red                         
338   &#34;    H   CH.sub.3       H     CH.sub.3                              
                                         &#34;                                
339   &#34;    H   CH.sub.2 CH.sub.2 OCOOC.sub.2 H.sub.5                      
                              H     &#34;    &#34;                                
340   Br   Cl  CH.sub.3       H     &#34;    yellow-brown                     
__________________________________________________________________________
 
    
     
                                           TABLE 7                                 
__________________________________________________________________________
The dyestuffs of the following Table 7 correspond to the formula          
 ##STR237##                                                               
exp.                                         Shade on                     
no.                                                                       
   DK             R.sub.1 R.sub.2                                         
                               Y        R.sub.3                           
                                             PES                          
__________________________________________________________________________
341                                                                       
    ##STR238##    H       H    CH.sub.2 CH.sub.2 CH.sub.2                 
                                        CH.sub.3                          
                                             ruby                         
342                                                                       
    ##STR239##    H       H    &#34;        &#34;    &#34;                            
343                                                                       
    ##STR240##    NHCOCH.sub.3                                            
                          OCH.sub.3                                       
                               &#34;        H    navy blue                    
344                                                                       
    ##STR241##    &#34;       OC.sub.2 H.sub.5                                
                               &#34;        H    &#34;                            
345                                                                       
    ##STR242##    CH.sub.3                                                
                          H    CH.sub.2 CH.sub.2 CH.sub.2                 
                                        C.sub.2 H.sub.5                   
                                             scarlet-red                  
__________________________________________________________________________
 
    
     
                                           TABLE 8                                 
__________________________________________________________________________
exp. no. 346                                                              
       ##STR243##                                navy blue                
exp. no. 347                                                              
       ##STR244##                                &#34;                        
__________________________________________________________________________
 
    
     
                                           TABLE 9                                 
__________________________________________________________________________
The dyestuffs of the following Table 9 correspond to the formula          
 ##STR245##                                                               
exp.                                         Shade on                     
no.                                                                       
   DK             R.sub.1 R.sub.2                                         
                               Y        R.sub.3                           
                                             PES                          
__________________________________________________________________________
348                                                                       
    ##STR246##    H       H    CH.sub.2 CH.sub.2 CH.sub.2                 
                                        CH.sub.3                          
                                             ruby                         
349                                                                       
    ##STR247##    H       H    &#34;        &#34;    &#34;                            
350                                                                       
    ##STR248##    NHCOCH.sub.3                                            
                          OCH.sub.3                                       
                               &#34;        H    navy blue                    
351                                                                       
    ##STR249##    &#34;       OC.sub.2 H.sub.5                                
                               &#34;        H    &#34;                            
352                                                                       
    ##STR250##    CH.sub.3                                                
                          H    &#34;        C.sub.2 H.sub.5                   
                                             scarlet-red                  
__________________________________________________________________________
 
    
     
                                           TABLE 10                                
__________________________________________________________________________
exp. no. 353                                                              
       ##STR251##                                navy blue                
exp. no. 354                                                              
       ##STR252##                                navy blue                
__________________________________________________________________________
 
    
     
                                           TABLE 11                                
__________________________________________________________________________
The dyestuffs of the following Table 11 correspond to formula             
 ##STR253##                                                               
exp.                                                                      
no.                                                                       
   DK             R.sub.1 R.sub.2                                         
                               Y        R.sub.3                           
                                             Shade on PES                 
__________________________________________________________________________
355                                                                       
    ##STR254##    H       H    CH.sub.2 CH.sub.2 CH.sub.2                 
                                        CH.sub.3                          
                                             ruby                         
356                                                                       
    ##STR255##    H       H                                               
                                ##STR256##                                
                                        CH.sub.3                          
                                             ruby                         
357                                                                       
    ##STR257##    NHCOCH.sub.3                                            
                          OCH.sub.3                                       
                               C.sub.3 H.sub.6                            
                                        H    navy blue                    
358                                                                       
    ##STR258##    &#34;       OC.sub.2 H.sub.5                                
                               &#34;        H    &#34;                            
359                                                                       
    ##STR259##    CH.sub.3                                                
                          H    &#34;        C.sub.2 H.sub.5                   
                                             scarlet-red                  
__________________________________________________________________________
 
    
     
                                           TABLE 12                                
__________________________________________________________________________
exp. no. 360                                                              
       ##STR260##                                        navy blue        
exp. no. 361                                                              
       ##STR261##                                        navy             
__________________________________________________________________________
                                                         blue             
 
    
     
                                           TABLE 13                                
__________________________________________________________________________
The dyestuffs of Table 13 correspond to formula                           
 ##STR262##                                                               
exp.                                                                      
no.                                                                       
   DK             R.sub.1 R.sub.2                                         
                               Y        R.sub.3                           
                                             Shade on PES                 
__________________________________________________________________________
362                                                                       
    ##STR263##    H       H    CH.sub.2 CH.sub.2 CH.sub.2                 
                                        CH.sub.3                          
                                             ruby                         
363                                                                       
   &#34;              H       H                                               
                                ##STR264##                                
                                        &#34;    &#34;                            
364                                                                       
    ##STR265##    NHCOCH.sub.3                                            
                          OCH.sub.3                                       
                               C.sub.3 H.sub.6                            
                                        H    navy blue                    
365                                                                       
    ##STR266##    NHCOCH.sub.3                                            
                          OC.sub.2 H.sub.5                                
                               C.sub.3 H.sub.6                            
                                        H    navy blue                    
366                                                                       
    ##STR267##    CH.sub.3                                                
                          H    &#34;        C.sub.2 H.sub.5                   
                                             scarlet-red                  
__________________________________________________________________________
 
    
     
                                           TABLE 14                                
__________________________________________________________________________
exp. no. 367                                                              
       ##STR268##                                         navy blue       
exp. no. 368                                                              
       ##STR269##                                         navy blue       
__________________________________________________________________________
 
    
     
                                           TABLE 15                                
__________________________________________________________________________
The dyestuffs of following Table 15 correspond to formula                 
 ##STR270##                                                               
exp.                                                                      
no.                                                                       
   M  R.sub.12                                                            
          R.sub.8 R.sub.3      Shade on PES                               
__________________________________________________________________________
369                                                                       
   H  Br  CH.sub.3                                                        
                  H            navy blue                                  
370                                                                       
   H  &#34;   C.sub.2 H.sub.5                                                 
                  H            &#34;                                          
371                                                                       
   H  &#34;   C.sub.2 H.sub.4 OCH.sub.3                                       
                  H            &#34;                                          
372                                                                       
   Cl Cl  &#34;       H            &#34;                                          
373                                                                       
   H  &#34;   C.sub.2 H.sub.4 OCH.sub.3                                       
                  H            &#34;                                          
374                                                                       
   H  &#34;   C.sub.2 H.sub.5                                                 
                  H            &#34;                                          
375                                                                       
   H  &#34;   CH.sub.3                                                        
                  C.sub.2 H.sub.5                                         
                               greenish navy blue                         
376                                                                       
   H  &#34;   &#34;       CH.sub.2 CHCH.sub.2                                     
                               navy blue                                  
377                                                                       
   H  Br  &#34;       CH.sub.2 CHCHCl                                         
                               reddish navy blue                          
378                                                                       
   H  Cl  &#34;                                                               
                   ##STR271##  &#34;                                          
379                                                                       
   H  &#34;   &#34;       CH.sub.2 C.sub.6 H.sub.5                                
                               navy blue                                  
380                                                                       
   H  &#34;   C.sub.2 H.sub.5                                                 
                  CH.sub.2 CHCH.sub.2                                     
                               &#34;                                          
381                                                                       
   H  &#34;   &#34;       CH.sub.2 CHCHCl                                         
                               &#34;                                          
382                                                                       
   H  &#34;   &#34;                                                               
                   ##STR272##  reddish navy blue                          
383                                                                       
   H  Cl  CH.sub.3                                                        
                  C.sub.2 H.sub.4 C.sub.6 H.sub.5                         
                               greenish navy blue                         
384                                                                       
   H  &#34;   &#34;       C.sub.3 H.sub.6 OC.sub.6 H.sub.5                        
                               &#34;                                          
385                                                                       
   H  H   &#34;       CHCHCHCl     reddish navy blue                          
386                                                                       
   H                                                                      
J  &#34;  CH.sub.2 CHCH.sub.2                                                 
          &#34;                                                               
387                                                                       
   H  CN  &#34;       &#34;            greenish blue                              
388                                                                       
   H  &#34;   &#34;       C.sub.2 H.sub.5                                         
                               bluish green                               
__________________________________________________________________________
 
    
     
                                           TABLE 16                                
__________________________________________________________________________
The dyestuffs of following Table 16 correspond to formula                 
 ##STR273##                                                               
exp.                                                                      
no.                                                                       
   M  R.sub.12                                                            
          R.sub.8 R.sub.3      Shade on PES                               
__________________________________________________________________________
389                                                                       
   H  Br  CH.sub.3                                                        
                  H            navy blue                                  
390                                                                       
   H  &#34;   C.sub.2 H.sub.5                                                 
                  H            &#34;                                          
391                                                                       
   H  &#34;   C.sub.2 H.sub.4 OCH.sub.3                                       
                  H            &#34;                                          
392                                                                       
   H  Cl  CH.sub.3                                                        
                  H            &#34;                                          
393                                                                       
   Cl Cl  &#34;       H            &#34;                                          
394                                                                       
   H  &#34;   C.sub.2 H.sub.4 OCH.sub.3                                       
                  H            &#34;                                          
395                                                                       
   H  &#34;   C.sub.2 H.sub.5                                                 
                  H            &#34;                                          
396                                                                       
   H  &#34;   CH.sub.3                                                        
                  C.sub.2 H.sub.5                                         
                               greenish navy blue                         
397                                                                       
   H  &#34;   &#34;       CH.sub.2 CHCH.sub.2                                     
                               navy blue                                  
398                                                                       
   H  Br  &#34;       CH.sub.2 CHCHCl                                         
                               reddish navy blue                          
399                                                                       
   H  Cl  &#34;                                                               
                   ##STR274##  &#34;                                          
400                                                                       
   H  &#34;   &#34;       CH.sub.2 C.sub.6 H.sub.5                                
                               navy blue                                  
401                                                                       
   H  &#34;   C.sub.2 H.sub.5                                                 
                  CH.sub.2 CHCH.sub.2                                     
                               &#34;                                          
402                                                                       
   H  &#34;   &#34;       CH.sub.2 CHCHCl                                         
                               &#34;                                          
403                                                                       
   H  &#34;   &#34;                                                               
                   ##STR275##  reddish navy blue                          
404                                                                       
   H  Cl  CH.sub.3                                                        
                  C.sub.2 H.sub.4 C.sub.6 H.sub.5                         
                               greenish navy blue                         
405                                                                       
   H  &#34;   &#34;       C.sub.3 H.sub.6 OC.sub.6 H.sub.5                        
                               &#34;                                          
406                                                                       
   H  H   &#34;       CHCHCHCl     reddish navy blue                          
407                                                                       
   H                                                                      
J  &#34;  CH.sub.2 CHCH.sub.2                                                 
          &#34;                                                               
408                                                                       
   H  CN  &#34;       &#34;            greenish blue                              
409                                                                       
   H  &#34;   &#34;       C.sub.2 H.sub.5                                         
                               bluish green                               
__________________________________________________________________________
 
    
     
                                           TABLE 17                                
__________________________________________________________________________
The dyestuffs of following Table 17 correspond to formula                 
 ##STR276##                                                               
exp.                                                                      
no. M   R.sub.12                                                          
             R.sub.8  R.sub.3       Shade on PES                          
__________________________________________________________________________
410 H   Br   CH.sub.3 H             navy blue                             
411 H   &#34;    C.sub.2 H.sub.5                                              
                      H             &#34;                                     
412 H   &#34;    C.sub.2 H.sub.4 OCH.sub.3                                    
                      H             &#34;                                     
413 H   Cl   CH.sub.3 H             &#34;                                     
414 Cl  Cl   &#34;        H             &#34;                                     
415 H   &#34;    C.sub.2 H.sub.4 OCH.sub.3                                    
                      H             &#34;                                     
416 H   &#34;    C.sub.2 H.sub.5                                              
                      H             &#34;                                     
417 H   &#34;    CH.sub.3 C.sub.2 H.sub.5                                     
                                    greenish navy blue                    
418 H   &#34;    &#34;        CH.sub.2 CHCH.sub.2                                 
                                    navy blue                             
419 H   Br   &#34;        CH.sub.2 CHCHCl                                     
                                    reddish navy blue                     
420 H   Cl   &#34;                                                            
                       ##STR277##   &#34;                                     
421 H   &#34;    &#34;        CH.sub.2 C.sub.6 H.sub.5                            
                                    navy blue                             
422 H   &#34;    C.sub.2 H.sub.5                                              
                      CH.sub.2 CHCH.sub.2                                 
                                    &#34;                                     
423 H   &#34;    &#34;        CH.sub.2 CHCHCl                                     
                                    &#34;                                     
424 H   &#34;    &#34;                                                            
                       ##STR278##   reddish navy blue                     
425 H   Cl   CH.sub.3 C.sub.2 H.sub.4 C.sub.6 H.sub.5                     
                                    greenish navy blue                    
426 H   &#34;    &#34;        C.sub.3 H.sub.6 OC.sub.6 H.sub.5                    
                                    &#34;                                     
427 H   H    &#34;        CHCHCHCl      reddish navy blue                     
428 H                                                                     
J   &#34;   CH.sub.2 CHCH.sub.2                                               
             &#34;                                                            
429 H   CN   &#34;        &#34;             greenish blue                         
430 H   &#34;    &#34;        C.sub.2 H.sub.5                                     
                                    bluish green                          
__________________________________________________________________________
 
    
     
                                           TABLE 18                                
__________________________________________________________________________
The dyestuffs of following Table 18 correspond to formula                 
 ##STR279##                                                               
exp.                                                                      
no.                                                                       
   M    R.sub.12                                                          
             R.sub.8  R.sub.3       Shade on PES                          
__________________________________________________________________________
431                                                                       
   H    Br   CH.sub.3 H             navy blue                             
432                                                                       
   H    &#34;    C.sub.2 H.sub.5                                              
                      H             &#34;                                     
433                                                                       
   H    &#34;    C.sub.2 H.sub.4 OCH.sub.3                                    
                      H             &#34;                                     
434                                                                       
   H    Cl   CH.sub.3 H             &#34;                                     
435                                                                       
   Cl   Cl   &#34;        H             &#34;                                     
436                                                                       
   H    &#34;    C.sub.2 H.sub.4 OCH.sub.3                                    
                      H             &#34;                                     
437                                                                       
   H    &#34;    C.sub.2 H.sub.5                                              
                      H             &#34;                                     
438                                                                       
   H    &#34;    CH.sub.3 C.sub.2 H.sub.5                                     
                                    greenish navy blue                    
439                                                                       
   H    &#34;    &#34;        CH.sub.2 CHCH.sub.2                                 
                                    navy blue                             
440                                                                       
   H    Br   &#34;        CH.sub.2 CHCHCl                                     
                                    reddish navy blue                     
441                                                                       
   H    Cl   &#34;                                                            
                       ##STR280##   &#34;                                     
442                                                                       
   H    &#34;    &#34;        CH.sub.2 C.sub.6 H.sub.5                            
                                    navy blue                             
443                                                                       
   H    &#34;    C.sub.2 H.sub.5                                              
                      CH.sub.2 CHCH.sub.2                                 
                                    &#34;                                     
444                                                                       
   H    &#34;    &#34;        CH.sub.2 CHCHCl                                     
                                    &#34;                                     
445                                                                       
   H    &#34;    &#34;                                                            
                       ##STR281##   reddish navy blue                     
446                                                                       
   H    Cl   CH.sub.3 C.sub.2 H.sub.4 C.sub.6 H.sub.5                     
                                    greenish navy blue                    
447                                                                       
   H    &#34;    &#34;        C.sub.3 H.sub.6 OC.sub.6 H.sub.5                    
                                    &#34;                                     
448                                                                       
   H    H    &#34;        CHCHCHCl      reddish navy blue                     
449                                                                       
   H                                                                      
J  &#34;    CH.sub.2 CHCH.sub.2                                               
             &#34;                                                            
450                                                                       
   H    CN   &#34;        &#34;             greenish blue                         
451                                                                       
   H    &#34;    &#34;        C.sub.2 H.sub.5                                     
                                    bluish green                          
__________________________________________________________________________
 
    
     
                                           TABLE 19                                
__________________________________________________________________________
The dyestuffs of the following Table 19 correspond to formula             
 ##STR282##                                                               
exp.                                                                      
no. B        Z     R.sub.1 R.sub.2 R.sub.3     Shade on                   
__________________________________________________________________________
                                               PES                        
452 O                                                                     
              ##STR283##                                                  
                   CH.sub.3                                               
                           H       C.sub.2 H.sub.5                        
                                               blue                       
453 O        &#34;     &#34;       H       C.sub.4 H.sub.9                        
                                               &#34;                          
454 CHNO.sub.2                                                            
             &#34;     &#34;       H       C.sub.2 H.sub.5                        
                                               greenish blue              
455                                                                       
     ##STR284##                                                           
             &#34;     &#34;       H       &#34;           &#34;                          
456 O        &#34;     NHCOCH.sub.3                                           
                           H       &#34;           reddish blue               
457 O        N     CH.sub.3                                               
                           H       &#34;           violet                     
458 O        &#34;     NHCOCH.sub.3                                           
                           OCH.sub.3                                      
                                   H           navy blue                  
459 O        &#34;     &#34;       &#34;       CH.sub.2 CHCH.sub.2                    
                                               &#34;                          
460 O        &#34;     &#34;       &#34;       CH.sub.2 HCCHCl                        
                                               &#34;                          
461 O        &#34;     &#34;       OC.sub.2 H.sub.5                               
                                   &#34;           &#34;                          
462 O        &#34;     &#34;       &#34;       CH.sub.2 CHCH.sub.2                    
                                               &#34;                          
463 O        &#34;     &#34;       OC.sub.2 H.sub.4 OCH.sub.3                     
                                   &#34;           &#34;                          
464 O        &#34;     &#34;       OC.sub.2 H.sub.5                               
                                   H           &#34;                          
465 O.sub.2 NCH                                                           
             &#34;     CH.sub.3                                               
                           H       C.sub.2 H.sub.5                        
                                               blue                       
466                                                                       
     ##STR285##                                                           
             &#34;     &#34;       OCH.sub.3                                      
                                   &#34;           &#34;                          
__________________________________________________________________________
 
    
     
                                           TABLE 20                                
__________________________________________________________________________
The dyestuffs of the following Table 20 correspond to formula             
 ##STR286##                                                               
exp.                                                                      
no.                                                                       
   B         Z     R.sub.1 R.sub.2 R.sub.3     Shade on                   
__________________________________________________________________________
                                               PES                        
467                                                                       
   O                                                                      
              ##STR287##                                                  
                   CH.sub.3                                               
                           H       C.sub.2 H.sub.5                        
                                               blue                       
468                                                                       
   O         &#34;     &#34;       H       C.sub.4 H.sub.9                        
                                               &#34;                          
469                                                                       
   CHNO.sub.2                                                             
             &#34;     &#34;       H       C.sub.2 H.sub.5                        
                                               greenish blue              
470                                                                       
    ##STR288##                                                            
             &#34;     &#34;       H       &#34;           &#34;                          
471                                                                       
   O         &#34;     NHCOCH.sub.3                                           
                           H       &#34;           reddish blue               
472                                                                       
   O         N     CH.sub.3                                               
                           H       &#34;           violet                     
473                                                                       
   O         &#34;     NHCOCH.sub.3                                           
                           OCH.sub.3                                      
                                   H           navy blue                  
474                                                                       
   O         &#34;     &#34;       &#34;       CH.sub.2 CHCH.sub.2                    
                                               &#34;                          
475                                                                       
   O         &#34;     &#34;       &#34;       CH.sub.2 HCCHCl                        
                                               &#34;                          
476                                                                       
   O         &#34;     &#34;       OC.sub.2 H.sub.5                               
                                   &#34;           &#34;                          
477                                                                       
   O         &#34;     &#34;       &#34;       CH.sub.2 CHCH.sub.2                    
                                               &#34;                          
478                                                                       
   O         &#34;     &#34;       OC.sub.2 H.sub.4 OCH.sub.3                     
                                   &#34;           &#34;                          
479                                                                       
   O         &#34;     &#34;       OC.sub.2 H.sub.5                               
                                   H           &#34;                          
480                                                                       
   O.sub.2 NCH                                                            
             &#34;     CH.sub.3                                               
                           H       C.sub.2 H.sub.5                        
                                               blue                       
481                                                                       
    ##STR289##                                                            
             &#34;     &#34;       OCH.sub.3                                      
                                   &#34;           &#34;                          
__________________________________________________________________________
 
    
     
                                           TABLE 21                                
__________________________________________________________________________
The dyestuffs of the following Table 21 correspond to formula             
 ##STR290##                                                               
exp.                                                                      
no.                                                                       
   B         Z     R.sub.1 R.sub.2 R.sub.3     Shade on                   
__________________________________________________________________________
                                               PES                        
482                                                                       
   O                                                                      
              ##STR291##                                                  
                   CH.sub.3                                               
                           H       C.sub.2 H.sub.5                        
                                               blue                       
483                                                                       
   O         &#34;     &#34;       H       C.sub.4 H.sub.9                        
                                               &#34;                          
484                                                                       
   CHNO.sub.2                                                             
             &#34;     &#34;       H       C.sub.2 H.sub.5                        
                                               greenish blue              
485                                                                       
    ##STR292##                                                            
             &#34;     &#34;       H       &#34;           &#34;                          
486                                                                       
   O         &#34;     NHCOCH.sub.3                                           
                           H       &#34;           reddish blue               
487                                                                       
   O         N     CH.sub.3                                               
                           H       &#34;           violet                     
488                                                                       
   O         &#34;     NHCOCH.sub.3                                           
                           OCH.sub.3                                      
                                   H           navy blue                  
489                                                                       
   O         &#34;     &#34;       &#34;       CH.sub.2 CHCH.sub.2                    
                                               &#34;                          
490                                                                       
   O         &#34;     &#34;       &#34;       CH.sub.2 HCCHCl                        
                                               &#34;                          
491                                                                       
   O         &#34;     &#34;       OC.sub.2 H.sub.5                               
                                   &#34;           &#34;                          
492                                                                       
   O         &#34;     &#34;       &#34;       CH.sub.2 CHCH.sub.2                    
                                               &#34;                          
493                                                                       
   O         &#34;     &#34;       OC.sub.2 H.sub.4 OCH.sub.3                     
                                   &#34;           &#34;                          
494                                                                       
   O         &#34;     &#34;       OC.sub.2 H.sub.5                               
                                   H           &#34;                          
495                                                                       
   O.sub.2 NCH                                                            
             &#34;     CH.sub.3                                               
                           H       C.sub.2 H.sub.5                        
                                               blue                       
497                                                                       
    ##STR293##                                                            
             &#34;     &#34;       OCH.sub.3                                      
                                   &#34;           &#34;                          
__________________________________________________________________________
 
    
     
                                           TABLE 22                                
__________________________________________________________________________
The dyestuffs of the following Table 22 correspond to formula             
 ##STR294##                                                               
exp.                                                                      
no.                                                                       
   B         Z     R.sub.1 R.sub.2 R.sub.3     Shade on                   
__________________________________________________________________________
                                               PES                        
498                                                                       
   O                                                                      
              ##STR295##                                                  
                   CH.sub.3                                               
                           H       C.sub.2 H.sub.5                        
                                               blue                       
499                                                                       
   O         &#34;     &#34;       H       C.sub.4 H.sub.9                        
                                               &#34;                          
500                                                                       
   CHNO.sub.2                                                             
             &#34;     &#34;       H       C.sub.2 H.sub.5                        
                                               greenish blue              
501                                                                       
    ##STR296##                                                            
             &#34;     &#34;       H       &#34;           &#34;                          
502                                                                       
   O         &#34;     NHCOCH.sub.3                                           
                           H       &#34;           reddish blue               
503                                                                       
   O         N     CH.sub.3                                               
                           H       &#34;           violet                     
504                                                                       
   O         &#34;     NHCOCH.sub.3                                           
                           OCH.sub.3                                      
                                   H           navy blue                  
505                                                                       
   O         &#34;     &#34;       &#34;       CH.sub.2 CHCH.sub.2                    
                                               &#34;                          
506                                                                       
   O         &#34;     &#34;       &#34;       CH.sub.2 HCCHCl                        
                                               &#34;                          
507                                                                       
   O         &#34;     &#34;       OC.sub.2 H.sub.5                               
                                   &#34;           &#34;                          
508                                                                       
   O         &#34;     &#34;       &#34;       CH.sub.2 CHCH.sub.2                    
                                               &#34;                          
509                                                                       
   O         &#34;     &#34;       OC.sub.2 H.sub.4 OCH.sub.3                     
                                   &#34;           &#34;                          
510                                                                       
   O         &#34;     &#34;       OC.sub.2 H.sub.5                               
                                   H           &#34;                          
511                                                                       
   O.sub.2 NCH                                                            
             &#34;     CH.sub.3                                               
                           H       C.sub.2 H.sub.5                        
                                               blue                       
512                                                                       
    ##STR297##                                                            
             &#34;     &#34;       OCH.sub.3                                      
                                   &#34;           &#34;                          
__________________________________________________________________________
 
    
     
                                           TABLE 23                                
__________________________________________________________________________
The dyestuffs of the following Table 23 correspond to formula             
 ##STR298##                                                               
exp.                                                                      
no.                                                                       
   R.sub.11                                                               
       R.sub.12                                                           
           R.sub.13                                                       
               R.sub.1 R.sub.2                                            
                            R.sub.3  R.sub.10                             
                                         Shade on PES                     
__________________________________________________________________________
513                                                                       
   CN  H   NO.sub.2                                                       
               H       H    CH.sub.3 CH.sub.3                             
                                         1 ruby                           
514                                                                       
   &#34;   H   &#34;   H       H    &#34;        H   2 ruby                           
515                                                                       
   &#34;   H   &#34;   H       H    &#34;        H   3 ruby                           
516                                                                       
   &#34;   H   &#34;   H       H    &#34;        H   4 ruby                           
517                                                                       
   &#34;   H   &#34;   H       H    &#34;        H   5 ruby                           
518                                                                       
   Cl  Cl  &#34;   H       H    &#34;        CH.sub.3                             
                                         1 yellow-brown                   
519                                                                       
   Cl  Cl  &#34;   H       H    &#34;        H   2 yellow-brown                   
520                                                                       
   NO.sub.2                                                               
       Cl  &#34;   NHCOCH.sub.3                                               
                       OCH.sub.3                                          
                            H        CH.sub.3                             
                                         1 navy blue                      
521                                                                       
   &#34;   Cl  &#34;   &#34;       &#34;    H        H   2 navy blue                      
522                                                                       
   &#34;   Cl  &#34;   &#34;       &#34;    CH.sub.2 CHCH.sub.2                           
                                     H   2 navy blue                      
523                                                                       
   &#34;   CN  &#34;   CH.sub.3                                                   
                       &#34;    CH.sub.3 H   2 blue                           
524                                                                       
   &#34;   CN  &#34;   &#34;       H    &#34;        H   2 reddish blue                   
__________________________________________________________________________
 
    
     
                                           TABLE 24                                
__________________________________________________________________________
The dyestuffs of the following Table 25 correspond to formula             
 ##STR299##                                                               
exp.                                                                      
no.                                                                       
   R.sub.11                                                               
       R.sub.12                                                           
           R.sub.13                                                       
               R.sub.1 R.sub.2                                            
                            R.sub.3    R.sub.10                           
                                           n Shade on PES                 
__________________________________________________________________________
525                                                                       
   CN  H   NO.sub.2                                                       
               H       H    CH.sub.3   CH.sub.3                           
                                           1 ruby                         
526                                                                       
   &#34;   H   &#34;   H       H    &#34;          H   2 &#34;                            
527                                                                       
   Cl  Cl  &#34;   H       H    &#34;          H   2 yellow-brown                 
528                                                                       
   NO.sub.2                                                               
       Cl  &#34;   NHCOCH.sub.3                                               
                       OCH.sub.3                                          
                            H          H   2 navy blue                    
529                                                                       
   &#34;   Br  &#34;   &#34;       &#34;    H          CH.sub.3                           
                                           1 &#34;                            
530                                                                       
   &#34;   CN  &#34;   CH.sub.3                                                   
                       &#34;    CH.sub.3   H   2 blue                         
531                                                                       
   &#34;   &#34;   &#34;   &#34;       H    C.sub.2 H.sub.5                               
                                       H   2 reddish blue                 
532                                                                       
   &#34;   &#34;   &#34;   CH.sub.3                                                   
                       OCH.sub.3                                          
                            CH.sub.3   H   1 blue                         
533                                                                       
   &#34;   &#34;   &#34;   CH.sub.3                                                   
                       &#34;    C.sub.2 H.sub.5                               
                                       H   1 &#34;                            
534                                                                       
   Cl  H   NO.sub.2                                                       
               H       H    CH.sub.2 CH.sub.2 OCOCH.sub.3                 
                                       H   2 scarlet                      
535                                                                       
   CN  CN  &#34;   CH.sub.3                                                   
                       H    C.sub.2 H.sub.5                               
                                       H   2 blue                         
__________________________________________________________________________
 
    
     
                                           TABLE 25                                
__________________________________________________________________________
The dyestuffs of following Table 25 correspond to formula                 
 ##STR300##                                                               
exp.                                                                      
no.                                                                       
   R.sub.11                                                               
       R.sub.12                                                           
           R.sub.1 R.sub.2                                                
                        R.sub.3  m n Q      Shade on PES                  
__________________________________________________________________________
536                                                                       
   NO.sub.2                                                               
       CN  CH.sub.3                                                       
                   OCH.sub.3                                              
                        CH.sub.3 1 3                                      
                                      ##STR301##                          
                                            blue                          
537                                                                       
   &#34;   &#34;   &#34;       H    &#34;        1 3 &#34;      reddish blue                  
538                                                                       
   &#34;   Br  &#34;       H    C.sub.2 H.sub.5                                   
                                 1 3 &#39;      violet                        
539                                                                       
   &#34;   Cl  NHCOCH.sub.3                                                   
                   OCH.sub.3                                              
                        CH.sub.2 CHCH.sub.2                               
                                 0 3 &#34;      navy blue                     
540                                                                       
   CN  H   H       H    CH.sub.3 1 3 &#34;      ruby                          
541                                                                       
   Cl  Cl  H       H    &#34;        1 3 &#34;      yellow-brown                  
542                                                                       
   NO.sub.2                                                               
       CN  CH.sub.3                                                       
                   H    &#34;        0 2 &#34;      reddish blue                  
543                                                                       
   &#34;   &#34;   &#34;       H    C.sub.2 H.sub.5                                   
                                 0 2 &#34;      &#34;                             
544                                                                       
   &#34;   &#34;   &#34;       OCH.sub.3                                              
                        CH.sub.3 0 3                                      
                                      ##STR302##                          
                                            blue                          
545                                                                       
   &#34;   &#34;   &#34;       H    C.sub.2 H.sub.5                                   
                                 1 3 &#34;      reddish blue                  
546                                                                       
   &#34;   &#34;   &#34;       H    CH.sub.3 1 3 &#34;      &#34;                             
547                                                                       
   CN  H   H       H    &#34;        1 3 &#34;      ruby                          
548                                                                       
   NO.sub.2                                                               
       Cl  NHCOCH.sub.3                                                   
                   OCH.sub.3                                              
                        H        1 3 &#34;      navy blue                     
__________________________________________________________________________
 
    
     APPLICATION EXAMPLE 
     The dyestuff obtained according to example 1 is converted by means of sand-grinding in the presence of dispersing agents, e.g. commercial lignin sulphonate, with subsequent fine disintegration, into an ultra-disperse dye preparation having an average particle size of 1 μm and a dilution ratio of 3.5:10. 
     12 parts of this preparation are made into a dispersion with 1000 parts of water, and added to the circulating liquor (13,000 parts, containing 30 parts of ammonium sulphate and 0.3 parts of formic acid as a buffer and optionally a carrier/levelling agent combination) at 60°. The pre-cleaned, compressed, cross-wound spool (1000 parts of polyester yarn on a plastic sleeve) is introduced, the dyeing autoclave closed, and heated in 35 minutes to 130°. After 90 minutes, cooling is effected to 80°, the exhausted liquor is drained, and the substrate thus dyed is washed thoroughly with cold water, and purified by reduction in the usual manner. It is then centrifuged and dried. A level, pure, deep ruby-red dyeing is obtained. 
     Dyeing of polyester yarn can be carried out analogously with examples 2-548, whereby yielding a level, deep dyeing. 
     The following table gives the λ max  -values of the above examples measured in dimethylformamide (DMF). 
     
         ______________________________________                                    
exp. no. λ.sub.max nm                                              
                       exp. no. λ.sub.max nm                       
______________________________________                                    
 8       532            26      614                                       
 9       527            27      511                                       
 10      508            28      530                                       
 11      494            29      517                                       
 12      490            30      542                                       
 13      489            31      600                                       
 14      520            32      541                                       
 15      510            33      545                                       
 16      530            35      517                                       
 17      527            36      537                                       
 18      435            37      524                                       
 19      443            38      534                                       
 20      433            39      544                                       
 21      432            42      604                                       
 22      583            44      645                                       
 23      604            45      660                                       
 24      615            46      630                                       
 25      616            48      625                                       
 49      622            70      456                                       
 50      625            71      459                                       
 51      626            72      446                                       
 52      661            73      487                                       
 53      529            74      492                                       
 54      550            75      488                                       
 55      556            76      497                                       
 56      510            77      509                                       
 57      587            78      502                                       
 58      584            79      526                                       
 59      558            80      524                                       
 60      549            81      532                                       
 61      605            82      536                                       
 62      605            83      443                                       
 63      606            84      532                                       
 64      572            85      538                                       
 65      561            86      515                                       
 66      525            87      495                                       
 67      451            88      490                                       
 68      457            89      489                                       
 69      449            90      521                                       
 91      511           113      525                                       
 92      531           114      534                                       
 93      532           115      544                                       
 94      435           118      605                                       
 95      443           120      646                                       
 96      433           121      661                                       
 97      432           122      631                                       
 98      584           124      625                                       
 99      605           125      622                                       
100      616           126      626                                       
101      617           127      626                                       
102      615           128      661                                       
103      512           129      530                                       
104      531           130      551                                       
105      518           131      557                                       
106      543           132      511                                       
107      601           133      588                                       
108      542           134      585                                       
109      545           135      559                                       
111      518           136      550                                       
112      538           137      606                                       
138      606           159      443                                       
139      607           160      440                                       
140      560           161      527                                       
141      562           162      539                                       
142      526           163      513                                       
143      452           164      493                                       
144      458           165      489                                       
145      449           166      488                                       
146      456           167      519                                       
147      459           168      509                                       
148      446           169      529                                       
149      487           170      526                                       
150      492           171      435                                       
151      489           172      443                                       
152      498           173      433                                       
153      509           174      432                                       
154      503           175      582                                       
155      527           176      603                                       
156      525           177      614                                       
157      527           178      615                                       
158      538           179      613                                       
180      510           206      528                                       
181      529           207      549                                       
182      516           208      555                                       
183      514           209      509                                       
184      599           210      586                                       
185      540           211      583                                       
186      544           212      557                                       
188      516           213      548                                       
189      536           214      604                                       
190      523           215      604                                       
191      533           216      605                                       
192      543           217      558                                       
195      603           218      560                                       
197      644           219      524                                       
198      659           220      450                                       
199      629           221      456                                       
201      624           222      448                                       
202      621           223      455                                       
203      624           224      458                                       
204      624           225      445                                       
205      660           226      486                                       
227      491           248      435                                       
228      487           249      441                                       
229      496           250      432                                       
230      508           251      431                                       
231      501           252      582                                       
232      525           253      603                                       
233      523           254      614                                       
234      531           255      615                                       
235      540           256      613                                       
236      442           257      510                                       
237      439           258      529                                       
238      530           259      516                                       
239      532           260      542                                       
240      513           261      599                                       
241      493           262      540                                       
242      487           263      544                                       
243      487           265      516                                       
244      519           266      536                                       
245      509           267      523                                       
246      529           268      533                                       
247      527           269      544                                       
272      603           295      560                                       
274      644           296      524                                       
275      659           297      445                                       
276      629           298      451                                       
278      624           299      448                                       
279      621           300      455                                       
280      624           301      458                                       
281      625           302      445                                       
282      660           303      486                                       
283      528           304      491                                       
284      549           305      487                                       
285      555           306      496                                       
286      509           307      508                                       
287      586           308      502                                       
288      583           309      525                                       
289      557           310      523                                       
290      548           311      530                                       
291      604           312      536                                       
292      604           313      442                                       
293      605           314      439                                       
294      558           315      440                                       
316      441           337      516                                       
317      437           338      533                                       
318      530           339      524                                       
319      534           340      439                                       
320      530           341      542                                       
321      524           342      537                                       
322      530           343      607                                       
323      443           344      610                                       
324      516           346      583                                       
325      533           347      622                                       
326      524           348      543                                       
327      439           349      537                                       
328      440           350      607                                       
329      441           351      609                                       
330      530           354      621                                       
331      530           354      621                                       
332      534           355      541                                       
333      530           356      540                                       
334      524           357      605                                       
335      530           358      607                                       
336      443           360      602                                       
361      628           386      599                                       
362      541           387      634                                       
363      539           388      637                                       
364      605           389      597                                       
365      607           390      597                                       
367      602           391      594                                       
368      629           392      598                                       
369      597           393      585                                       
370      597           394      593                                       
371      594           395      599                                       
372      581           396      603                                       
373      593           397      599                                       
374      600           398      589                                       
375      604           399      574                                       
376      599           401      600                                       
377      589           402      591                                       
378      573           403      575                                       
380      601           406      564                                       
381      592           407      598                                       
382      576           408      633                                       
385      565           409      635                                       
410      596           434      596                                       
411      596           435      583                                       
412      593           436      592                                       
413      597           437      598                                       
414      584           438      602                                       
415      592           439      598                                       
416      598           440      588                                       
417      602           441      571                                       
418      598           443      600                                       
419      588           444      590                                       
420      574           445      574                                       
422      598           448      564                                       
423      590           449      598                                       
424      574           450      633                                       
427      563           451      636                                       
428      596           452      611                                       
429      632           453      613                                       
430      635           455      638                                       
431      595           457      587                                       
432      596           458      610                                       
433      593           459      624                                       
460      613           487      586                                       
461      615           488      609                                       
462      626           489      623                                       
463      625           490      612                                       
464      610           491      614                                       
466      680           492      625                                       
467      612           493      624                                       
468      613           494      609                                       
470      639           497      679                                       
472      587           498      610                                       
473      611           499      612                                       
474      624           501      637                                       
475      613           503      586                                       
476      615           504      609                                       
477      627           505      623                                       
478      626           506      612                                       
479      611           507      614                                       
481      681           508      625                                       
482      610           509      624                                       
483      612           510      609                                       
485      637           512      679                                       
513      534           531      601                                       
514      535           532      614                                       
515      535           533      619                                       
516      536           534      511                                       
517      536           535      619                                       
518      440           536      613                                       
519      440           537      588                                       
520      597           538      557                                       
521      597           539      599                                       
522      599           540      533                                       
523      613           541      439                                       
524      587           542      587                                       
525      535           543      593                                       
526      536           544      613                                       
527      441           545      590                                       
528      598           546      587                                       
529      598           547      534                                       
530      595           548      598                                       
______________________________________                                    
 λ.sub.max -values