Patent Publication Number: US-4096145-A

Title: Naphtholactam derivatives

Description:
The present invention relates to compounds of the formula I ##STR2## where A is a radical of the formula ##STR3## n is 2 or 3, R is hydrogen or unsubstituted or substituted alkyl, cycloalkyl, aralkyl or aryl, R 1  is hydrogen, chlorine, bromine, alkyl, alkoxy, NO 2  or arylmercapto, R 2  is hydrogen or chlorine, R 3  is hydrogen, chlorine, bromine, alkyl, alkoxy, nitro, acylamino, alkylsulfonylamino, arylsulfonylamino, alkylmercapto, arylmercapto, arylsulfonyl, alkylsulfonyl, unsubstituted or N-substituted sulfamide, alkanoyl or aroyl, R 4  is hydrogen, chlorine, alkoxy, arylmercapto or alkylmercapto, or R 3  and R 4  together are a radical of the formula ##STR4## R 5  is hydrogen, chlorine or alkoxy, B is hydrogen, methyl, methoxy or chlorine, X is cyano or unsubstituted or substituted carbamoyl, Y is hydrogen, hydroxyl, alkyl of 1 to 4 carbon atoms, chlorine, bromine, C 1  to C 4  alkoxycarbonyl or unsubstituted or N-substituted carbamoyl, or X and Y together are a radical of the formula ##STR5## 
     More particularly, R is alkyl of 1 to 8 carbon atoms, hydroxyalkyl of 2 or 3 carbon atoms, alkoxyalkyl of 3 to 8 carbon atoms, β-chloroethyl, β-cyanoethyl, alkoxycarbonylethyl, where alkoxy is of 1 to 4 carbon atoms, carbamoylethyl, N-monosubstituted or N,N-disubstituted alkylcarbamoylethyl, where alkyl is of 1 to 4 carbon atoms, cyclohexyl, benzyl, phenylethyl or phenyl. 
     Specific examples of R are propyl, butyl, hexyl, β-ethylhexyl, β-hydroxyethyl or β-hydroxypropyl, methoxyethyl, ethoxyethyl, methoxypropyl, ethoxypropyl, butoxypropyl, amyloxypropyl, methoxycarbonylethyl, ethoxycarbonylethyl or butoxycarbonylethyl and preferably methyl, ethyl or β-cyanoethyl. 
     Examples of alkyl, alkoxy and arylmercapto groups R 1  are methyl, ethyl, methoxy, ethoxy and phenylmercapto which is unsubstituted or substituted by chlorine, methyl, methoxy, phenyl, phenoxy or methoxycarbonyl. 
     Examples of R 3  are the same radicals as those mentioned for R 1 , as well as naphthylmercapto, acylaminophenylmercapto, diacylaminophenylmercapto, acetylamino, propionylamino, benzoylamino which is unsubstituted by chlorine, methyl or methoxy, methylsulfonylamino, ethylsulfonylamino, phenylsulfonylamino, tolylsulfonylamino, methylmercapto, ethylmercapto, β-hydroxyethylmercapto, β-hydroxypropylmercapto, butylmercapto, methylsulfonyl, ethylsulfonyl, phenylsulfonyl, tolylsulfonyl, chlorophenylsulfonyl, acetyl, chloroacetyl, propionyl, butyryl, benzoyl which is unsubstituted or substituted by methyl, methoxy, chlorine or bromine, sulfamoyl, N-methyl-, N-ethyl-, N-butyl-, N-phenyl-, N-chlorophenyl, N-methylphenyl-, N-methoxyphenyl-, N-trifluoromethylphenyl-, N-methyl-N-phenyl-, N,N-dimethyl-, N,N-diethyl-, N,N-dipropyl- and N,N-dibutyl-sulfamoyl, pyrrolidinosulfonyl, piperidinosulfonyl or morpholinosulfonyl. R 3  may also be a radical of the formula NHCONH 2 , NHCONHCH 3  or NHCONHC 6  H 5 . 
     R 4  may be hydrogen, chlorine, or one of the alkoxy, alkylmercapto and arylmercapto radicals mentioned for R 1 . 
     Examples of alkoxy radicals R 5  are methoxy and ethoxy. Examples of N-substituted carbamoyl radicals Y are CONHCH 3 , CONHC 2  H 5 , CONHC 4  H 9 , CONHC 2  H 4  OH, CON(CH 3 ) 2 , CON(C 3  H 7 ) 2 , CON(C 4  H 9 ) 2  and ##STR6## 
     The compounds of the formula I may be manufactured by reacting compounds of the formula II ##STR7## where X 1  is oxygen or sulfur and A.sup.⊖ is an anion, and alkyl is of 1 to 4 carbon atoms, with compounds of the formula A--H 2 . 
     If X 1  is 0, a condensing agent must be present, whilst if X 1  is S or the compounds containing the S-alkyl groups are used, this is not necessary. 
     Suitable condensing agents are phosphorus halides, eg. phosphorus pentachloride, phosphorus trichloride, phosphorus oxytribromide and especially phosphorus oxytrichloride. 
     The reaction may be carried out in an inert solvent, eg. a glycol diether or polyglycol diether, butyrolactone, toluene, chlorobenzene, dichlorobenzene, nitrobenzene or dioxane, or in an excess of the condensing agent. 
     If the reaction of the naphtholactam derivatives is carried out without a condensing agent, the above solvents may again be used; additional examples of suitable solvents are pyridine, glacial acetic acid, dimethylformamide or N-methylpyrrolidone. 
     The compounds of the formula ##STR8## where T is oxygen and R and Y have the stated meanings, or the R bound to the ring nitrogen and T together are a radical of the formula ##STR9## and B, the other R and Y have the stated meanings, may be manufactured by reacting compounds of the formula 
     
         Y--COCH.sub.2 COO--alkyl 
    
     with compounds of the formula ##STR10## Suitable reaction conditions are similar to those for the manufacture of, for example, 2-hydroxy-3-cyano-6-pyridones. 
     The reactions are known in principle. Details may be found in the Examples, in which parts and percentages are by weight. 
     The invention in particular relates to compounds of the formula I, where A is a radical of the formula ##STR11## n is 2 or 3, R is hydrogen, alkyl of 1 to 12 carbon atoms, hydroxyalkyl of 2 or 3 carbon atoms, alkoxyalkyl of 3 to 8 carbon atoms, β-chloroethyl, β-cyanoethyl, alkoxycarbonylethyl, where alkoxy is of 1 to 4 carbon atoms, carbamoylethyl, N-mono- or N-di-alkylcarbamoylethyl, where alkyl is of 1 to 4 carbon atoms, cyclohexyl, benzyl, phenylethyl or phenyl, R 1  is hydrogen, chlorine, bromine, methyl, ethyl, methoxy, ethoxy, nitro, phenylmercapto or phenylmercapto substituted by chlorine, methyl or methoxy, R 2  is hydrogen or chlorine, R 3  is hydrogen, chlorine, bromine, methyl, ethyl, methoxy, ethoxy, phenoxy and nitro, alkanoylamino of 1 to 4 carbon atoms, benzoylamino, alkylsulfonylamino of 1 to 4 carbon atoms, phenylsulfonylamino, tolylsulfonylamino, alkylmercapto of 1 to 4 carbon atoms, phenylmercapto which is unsubstituted or substituted by chlorine, methyl or methoxy, alkylsulfonyl of 1 to 4 carbon atoms, phenylsulfonyl, tolylsulfonyl, sulfamoyl which is unsubstituted or is monosubstituted or disubstituted by alkyl of 1 to 8 carbon atoms, hydroxyalkyl of 2 or 3 carbon atoms, alkoxyalkyl of a total of 3 to 11 carbon atoms, β-cyanoethyl, β-chloroethyl, cyclohexyl, phenylalkyl (where alkyl is of 1 to 4 carbon atoms) or phenyl, sulfopiperidide, sulfopyrrolidide, sulfomorpholide, alkanoyl of 1 to 4 carbon atoms, chloroacetyl, β-chloropropionyl, or benzoyl which is unsubstituted or substituted by chlorine, methyl or methoxy, R 4  is hydrogen, chlorine, methoxy, ethoxy, alkylmercapto of 1 to 4 carbon atoms or phenylmercapto which is unsubstituted or substituted by chlorine, methyl or methoxy, R 3  and R 4  together are a radical of the formula ##STR12## R 5  is hydrogen, chlorine, methoxy or ethoxy, B is hydrogen, methyl, methoxy or chlorine, X is cyano, carbamoyl or CONHR, Y is hydrogen, hydroxyl, alkyl of 1 to 4 carbon atoms, chlorine, bromine, alkoxycarbonyl (where alkoxy is of 1 to 4 carbon atoms) or CONHR, or X and Y together are a radical of the formula ##STR13## 
     Dyes which are industrially particularly important are those of the formula I a ##STR14## where B 1  is hydrogen, alkylsulfonyl of 1 to 4 carbon atoms, allylsulfonyl, propargylsulfonyl, alkanoyl of 2 to 8 carbon atoms, benzoyl, alkylmercapto of 1 to 4 atoms or phenylmercapto, A 1  is a radical of the formula ##STR15## B 2  is hydrogen or methyl, and R and X have the stated meanings. 
     Specific examples of radicals B 1 , in addition to those already mentioned, are methylsulfonyl, ethylsulfonyl, propylsulfonyl and butylsulfonyl, acetyl, propionyl, butyryl, hexanoyl, β-ethylhexanoyl and methylmercapto, ethylmercapto, propylmercapto and butylmercapto. 
     X is preferably cyano. 
     Examples of preferred radicals R are methyl, ethyl, n-propyl and i-propyl, n-butyl and i-butyl, ω-hydroxyethyl and ω-hydroxypropyl, and ω-alkoxyethyl and ω-alkoxypropyl, where alkoxy is of 1 to 4 carbon atoms. 
     The compounds of the formula I may be used as dyes for textile material, especially made of polyesters, and for coloring plastics, eg. polystyrene, polycarbonate, polyolefins, polyesters, polyacrylonitrile and nylons, so as to retain their transparency. 
     The new dyes give brilliant hues ranging from orange to blue, which have excellent fastness to light, thermofixation and wet treatments. The fact that some of the dyes are of very high tinctorial strength should also be singled out. 
    
    
     EXAMPLE 1 
     180 parts of phosphorus oxychloride are added dropwise, at 80° C, to a mixture of 1,500 parts of ethylene glycol dimethyl ether, 169 parts of naphtholactam and 170 parts of 1-ethyl-3-cyano-6-hydroxypyrid-2-one. After a short time, a red solution forms, from which red crystals begin to separate out. The mixture is stirred for 4 hours at 80° C and 1,000 parts of methanol are added whilst the mixture is cooling. After it has cooled, the product is filtered off, washed with methanol and dried. 267 parts of a dye of the structure ##STR16## are obtained in the form of dark red crystals. When used to dye polyesters from an aqueous bath, the dye gives brilliant yellowish red hues having very good fastness properties. 
     Dyes with very similar hues are obtained if 1-ethyl-3-cyano-6-hydroxypyrid-2-one is replaced by the corresponding 1-propyl-, 1-butyl-, 1-(3-methoxypropyl)- or 1-(2-ethyl-hexyl)-compounds. 
     When 6-ethoxy-1,8-naphtholactam is condensed by a similar method with N-substituted 3-cyano-6-hydroxypyrid-2-ones, dyes which dye polyesters in neutral red hues are obtained; the dyeings are outstandingly fast. 
     EXAMPLE 2 
     276 parts of N-ethyl-4-bromonaphtholactam and 226 parts of 1-phenyl-3-cyano-4-methyl-6-hydroxypyrid-2-one are introduced into 1,000 parts of toluene and the mixture is stirred at 90° C. 165 parts of phosphorus oxychloride are added dropwise in the course of an hour and the mixture is stirred for a further 2 hours at 90° C. An equal volume of methanol is then added and the mixture is allowed to cool whilst stirring. After filtering off, washing with methanol and drying, 311 parts of a dye of the structure ##STR17## are obtained in the form of a dark crystal powder. 
     The dye may be used for mass-coloring polystyrene to give brilliant blue hues of good lightfastness and good heat stability. 
     Dyes having similar blue hues are obtained when N-ethyl-4-bromonaphtholactam is replaced by the corresponding N-butyl, N-methoxyethyl or N-cyclohexyl compounds. 
     EXAMPLE 3 
     The &#34;naphthostyrol-imide chloride&#34; obtained from 169 parts of naphtholactam by the method described in German Laid-Open Application DOS 1,445,624, and 209 parts of the benzimidazopyridone of the formula (B ═ H, Y ═ H) ##STR18## are introduced into 1,000 parts of nitrobenzene and the mixture is stirred at 85° C until the elimination of hydrogen chloride has ceased. After the mixture has cooled, the suspended crystals are filtered off, washed with ethanol and dried. 301 parts of a dye of the structure ##STR19## are obtained in the form of dark crystals. When used to dye polyesters from an aqueous bath, the dye gives violet dyeings which are outstandingly fast. Dyes with similar tinctorial properties are obtained if benzimidazopyridones substituted in the benz-nucleus (B ═ --CH 3 , --OCH 3 , --Cl, Y ═ H) are employed as the starting material. The analogous dye with Y ═ CH 3  and B ═ H is blue and may be used to color thermoplastics, giving fast blue hues. 
     EXAMPLE 4 
     385 parts of 2,4-bis-(phenylmercapto)-naphtholactam and 185 parts of 1-methyl-3-cyano-4-ethyl-6-hydroxypyrid-2-one are introduced into 1,000 parts of chlorobenzene and the mixture is stirred at 90° C. 165 parts of phosphorus oxychloride are added dropwise and stirring is continued for 1 hour at 90° C. 1,200 parts of methanol are now added to the reaction mixture, which is then left to stand for 24 hours. The product is then filtered off, washed with methanol and dried. 339 parts of a dye of the structure ##STR20## are obtained, which may be used for dyeing polyesters from an aqueous bath, and for mass-coloring polystyrene, giving pure reddish blue hues. 
     If 2,4-bis-(phenylmercapto)-naphtholactam is replaced by the corresponding 2,4-bis-(p-tolyl)- or 2,4-bis-(4-methoxyphenyl)- compounds, dyes giving neutral blue hues are obtained. 
     EXAMPLE 5 
     183 parts of naphtholactam-o-methyl ether and 250 parts of 1-(3-ethoxypropyl)-3-cyano-4,6-dihydroxypyrid-6-one are stirred into 1,200 parts of ethylene glycol and the mixture is heated to 125° C. It is then stirred for 8 hours at 125° - 130° C and the methanol formed is distilled off through a descending condenser. After the reaction mixture has cooled, it is filtered and the product is washed with ethanol and dried. 281 parts of a dye of the structure ##STR21## are obtained in the form of reddish brown crystals. The dye may be used for dyeing polyesters in orange red hues exhibiting a high level of fastness. 
     EXAMPLE 6 
     A mixture of 600 parts of butyrolactone, 277 parts of 4-phenylmercaptonaphtholactam and 155 parts of 1-methyl-3-cyano-6-hydroxypyrid-2-one is stirred at 80° C. 170 parts of phosphorus oxychloride are added dropwise and stirring is continued for 2 hours at 80° C. 1,000 parts of methanol are then added to the reaction mixture and the product is filtered off and rinsed with methanol. After drying, 299 parts of a dye of the structure ##STR22## are obtained in the form of brown crystals. The dye may be used for dyeing polyesters from an aqueous bath, giving vivid violet hues; the dyeings have outstanding light fastness and fastness to thermofixation. Dyes of a similar hue are obtained if the phenylmercapto-naphtholactam is replaced by the corresponding 4-tolylmercapto-, 4-methoxyphenylmercapto-, 4-chlorophenylmercapto- or 4-carbomethoxyphenylmercapto-naphtholactam. 
     EXAMPLE 7 
     271 parts of 4,5-benzoylene-naphtholactam (prepared as described in CA 53, 9183 g) and 239 parts of benzimidazopyridone of the formula ##STR23## are introduced into 1,200 parts of butyrolactone and the mixture is stirred at 120° C. 200 parts of phosphorus oxychloride are added dropwise and stirring is continued for 6 hours at 120° C. The product is filtered off at 80° C and is rinsed with warm ethanol. After drying, 399 parts of the dye of the structure ##STR24## are obtained in the form of red crystals. When worked into thermoplastics, the dye gives brilliant red hues having very good lightfastness. 
     EXAMPLE 8 
     328 parts of N-benzyl-4,5-dichloro-1,8-naphtholactam and 150 parts of 1-methyl-3-cyano-6-hydroxyoyrid-2-one are introduced into 1,200 parts of butyrolactone and the mixture is stirred at 90° C. 190 parts of phosphorus oxychloride are then added dropwise whilst stirring and the mixture is kept at 90° C for 12 hours. It is diluted with 800 parts of ethanol and the product is filtered off and washed with ethanol. After drying, 413 parts of the dye of the structure ##STR25## are obtained in the form of a dark crystal powder. The dye colors polystyrene in violet hues distinguished by very good lightfastness and heat stability. If 178 parts of 1-ethyl-3-cyano-4-methyl-6-hydroxypyrid-2-one are employed as the pyridone component, an analogous dye which may be used to color thermoplastics in blue hues is obtained. 
     EXAMPLE 9 
     307 parts of 3,4,5,6-tetrachloro-1,8-naphtholactam and 212 parts of 1-phenyl-3-cyano-6-hydroxypyrid-2-one are introduced into 1,500 parts of dehydrated nitrobenzene and the mixture is heated to 100° C. 300 parts of phosphorus oxychloride are added dropwise in the course of one hour and stirring is continued for 16 hours at 100° C. 500 parts of methanol are then added dropwise and the mixture is boiled for one hour under reflux. After filtering off, washing with methanol and drying, 443 parts of a dye of the structure ##STR26## are obtained in the form of a dark red crystal powder. When worked into thermoplastics, the dye gives red hues having excellent lightfastness. 
     If N-ethyl-3,4,5,6-tetrachloro-1,8-naphtholactam is used as the naphtholactam component, an analogous dye which colors thermoplastics in fast violet hues is obtained. 
     EXAMPLE 10 
     275 parts of the compound ##STR27## and 208 parts of 1-ethoxyethyl-3-cyano-6-hydroxypyrid-2-one are introduced into 2,000 parts of dichlorobenzene. The mixture is stirred at 90° C and 250 parts of phosphorus oxychloride are added in the course of 2 hours. Stirring is continued for 12 hours at 90° C and 1,000 parts of ethanol are then added carefully. The reaction mixture is boiled up briefly and is filtered warm. After washing the product with ethanol, and drying it, 398 parts of a dye of the structure ##STR28## are obtained in the form of dark crystals having a metallic gloss. When worked into polystyrene, the dye gives fast greenish blue colorations. 
     The further dyes shown in the Table were obtained by the processes of Examples 1 - 10. 
     
                                           TABLE 1                                 
__________________________________________________________________________
Dyes                                                                      
 ##STR29##                                                                
Ex-                                                                       
ample                                                                     
    R           R.sup.3      Y       Hue                                  
__________________________________________________________________________
11  (CH.sub.2).sub.3 OC.sub.5 H.sub.11                                    
                Cl           CH.sub.3                                     
                                     violet                               
12  (CH.sub.2).sub.2 COOC.sub.3 H.sub.7                                   
                H            CH.sub.3                                     
                                     reddish violet                       
13                                                                        
     ##STR30##  OC.sub.2 H.sub.5                                          
                             CH.sub.3                                     
                                     violet                               
14  CH.sub.2 C.sub.6 H.sub.5                                              
                NHCOC.sub.2 H.sub.5                                       
                             CH.sub.3                                     
                                     violet                               
15  CH.sub.3    SC.sub.6 H.sub.5                                          
                             C.sub.2 H.sub.5                              
                                     bluish violet                        
16  CH.sub.2 CH.sub.2 OH                                                  
                H            C.sub.4 H.sub.9                              
                                     violet                               
17  C.sub.6 H.sub.5                                                       
                SC.sub.4 H.sub.9                                          
                             C.sub.4 H.sub.9                              
                                     bluish violet                        
18  H           CH.sub. 3    Br      reddish violet                       
19  CH.sub.3    H            H       yellowish red                        
20  C.sub.2 H.sub.5                                                       
                Br           H       red                                  
21  C.sub.2 H.sub.5                                                       
                NO.sub.2     H       reddish violet                       
22  C.sub.2 H.sub.5                                                       
                OCH.sub.3    H       &#34;                                    
23  &#34;           NHCONHCH.sub.3                                            
                             H       &#34;                                    
24  &#34;           NHSO.sub.2 C.sub.2 H.sub.5                                
                             H       &#34;                                    
25  &#34;           SCH.sub.3    H       bluish violet                        
26  &#34;           SCH.sub.2 CHOHCH.sub.3                                    
                             H       &#34;                                    
27  &#34;           SO.sub.2 CH.sub.3                                         
                             H       bluish red                           
28  &#34;           SO.sub.2 C.sub.6 H.sub.4 CH.sub.3 (4)                     
                             H       &#34;                                    
29  &#34;           COCH.sub.3   H       red                                  
30  &#34;           COCH.sub.2 Cl                                             
                             H       &#34;                                    
31  &#34;           COC.sub.6 H.sub.5                                         
                             H       &#34;                                    
32  &#34;           SO.sub.2 N(C.sub.4 H.sub.9).sub.2                         
                             H       &#34;                                    
33  C.sub.3 H.sub.7 (n)                                                   
                H            H       yellowish red                        
34  &#34;           CH.sub.3     H       &#34;                                    
35  C.sub.3 H.sub.7 (iso)                                                 
                NHCOCH.sub.3 H       reddish violet                       
36  C.sub.4 H.sub.9 (n)                                                   
                 NHSO.sub.2 C.sub.6 H.sub.4 CH.sub.3 (4)                  
                             H       &#34;                                    
37  C.sub.4 H.sub.9 (n)                                                   
                SC.sub.2 H.sub.5                                          
                             H       bluish violet                        
38  &#34;           COC.sub.6 H.sub.4 CH.sub.3 (4)                            
                             H       red                                  
39  Ch.sub.2 CH.sub.2 OCH.sub.3                                           
                H            H       yellowish red                        
40  CH.sub.2 CH.sub.2 OCH.sub.3                                           
                SC.sub.6 H.sub.4 CH.sub.3 (4)                             
                             H       bluish violet                        
41  (CH.sub.2).sub.3 OC.sub.2 H.sub.5                                     
                SO.sub.2 N(CH.sub.3).sub.2                                
                             H       red                                  
42  (CH.sub.2).sub.3 OC.sub.4 H.sub.9                                     
                NHCOC.sub.6 H.sub.5                                       
                             H       reddish violet                       
43  (CH.sub.2).sub.3 OC.sub.4 H.sub.9                                     
                NHCOC.sub.6 H.sub.4 OCH.sub.3 (4)                         
                             H       &#34;                                    
44  CH.sub.2 CH(C.sub.2 H.sub.5)C.sub.4 H.sub.9                           
                Br           H       red                                  
45  CH.sub.2 CH.sub.2 CN                                                  
                 ##STR31##   H       bluish violet                        
46  CH.sub.2 CH.sub.2 COOCH.sub.3                                         
                NHCOC.sub.6 H.sub.4 OCH.sub.3 (4)                         
                             H       reddish violet                       
47  CH.sub.2 CH.sub.2 COOC.sub.4 H.sub.9                                  
                H            H       yellowish red                        
48  CH.sub.2 CH.sub.2 CONHC.sub.2 H.sub.5                                 
                SO.sub.2 C.sub.2 H.sub.5                                  
                             H       bluish red                           
49  CH.sub.2 CH.sub.2 CON(CH.sub.3).sub.2                                 
                SO.sub.2 C.sub.6 H.sub.4 Cl(4)                            
                             H       &#34;                                    
50  CH.sub.2 CH.sub.2 CON(C.sub.4 H.sub.9).sub.2                          
                H            H       yellowish red                        
51  CH.sub.2 CH.sub.2 C.sub.6 H.sub.5                                     
                H            H       &#34;                                    
52  &#34;                                                                     
                 ##STR32##   H       red                                  
53  C.sub.6 H.sub.5                                                       
                SCH.sub.2 CH.sub.2 OH                                     
                             H       bluish violet                        
54  &#34;           SC.sub.6 H.sub.4 OCH.sub.3 (4)                            
                             H       &#34;                                    
55  &#34;           SC.sub.6 H.sub.4 Cl(4)                                    
                             H       &#34;                                    
56  &#34;           SO.sub.2 NHC.sub.4 H.sub.9                                
                             H       red                                  
57  C.sub.6 H.sub.5                                                       
                 ##STR33##   H       &#34;                                    
58  CH.sub.3    SC.sub.6 H.sub.5                                          
                             OH      bluish red                           
59  C.sub.2 H.sub.5                                                       
                COC.sub.2 H.sub.5                                         
                             OH      reddish brown                        
60  &#34;           SO.sub.2 CH.sub.3                                         
                             OH      red                                  
61  &#34;           OC.sub.2 H.sub.5                                          
                             OH      reddish brown                        
62  &#34;           NHSO.sub.2 CH.sub.3                                       
                             OH      &#34;                                    
63  &#34;           SO.sub.2 N(C.sub.3 H.sub.7).sub.2                         
                             OH      red                                  
64  CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                                    
                COC.sub.6 H.sub.5                                         
                             OH      reddish brown                        
65  (CH.sub.2).sub.3 OCH.sub.3                                            
                H            OH      orange                               
66  (CH.sub.2).sub.3 OCH.sub.3                                            
                SC.sub.6 H.sub.4 OC.sub.6 H.sub.5                         
                             OH      bluish red                           
67  C.sub.3 H.sub.7                                                       
                H            OH      orange                               
68  &#34;           SO.sub.2 CH.sub.3                                         
                             OH      red                                  
69  &#34;           SO.sub.2 C.sub.6 H.sub.5                                  
                             OH      &#34;                                    
70  CH.sub.3    H            COOCH.sub.3                                  
                                     violet                               
71  &#34;           NHCONHC.sub.6 H.sub.5                                     
                             COOC.sub.2 H.sub.5                           
                                     bluish violet                        
72  &#34;           COC.sub.4 H.sub.9                                         
                             COOC.sub.2 H.sub.5                           
                                     violet                               
73  &#34;           NHSO.sub.2 CH.sub.3                                       
                             COOC.sub.2 H.sub.5                           
                                     &#34;                                    
74  &#34;           SO.sub.2 NHCH.sub.3                                       
                             COOC.sub.4 H.sub.9                           
                                     bluish violet                        
75  &#34;           SO.sub.2 NHC.sub.6 H.sub.4 CH.sub.3 (2)                   
                             COOC.sub.4 H.sub.9                           
                                     &#34;                                    
76  &#34;            SO.sub.2 N(C.sub.2 H.sub.5).sub.2                        
                             CONHC.sub.2 H.sub.5                          
                                     &#34;                                    
77  C.sub.2 H.sub.5                                                       
                H            CONHC.sub.2 H.sub.5                          
                                     violet                               
78  CH.sub.3    Cl           CON(CH.sub.3).sub.2                          
                                     &#34;                                    
79  C.sub.4 H.sub.9                                                       
                H            CON(CH.sub.3).sub.2                          
                                     &#34;                                    
80  CH.sub.3    SC.sub.6 H.sub.5                                          
                             CON(C.sub.2 H.sub.5).sub.2                   
                                     blue                                 
81  &#34;           COC.sub.6 H.sub.5                                         
                             CON(C.sub.3 H.sub.7).sub.2                   
                                     violet                               
__________________________________________________________________________
 
    
     
                       TABLE 2                                                     
______________________________________                                    
Dyes                                                                      
 ##STR34##                                                                
Ex.  R               R.sup.3      Y    Hue                                
______________________________________                                    
82   CH.sub.3        H            H    violet                             
83   CH.sub.3        SO.sub.2 CH.sub.3                                    
                                  H    bluish                             
                                       violet                             
84   CH.sub.3        SC.sub.6 H.sub.5                                     
                                  H    blue                               
85   CH.sub.2 CH.sub.2 COOC.sub.2 H.sub.5                                 
                     Cl           H    violet                             
86   CH.sub.2 CH.sub.2 CN                                                 
                     Br           H    &#34;                                  
87   CH.sub.2 CH.sub.2 CON(CH.sub.3).sub.2                                
                     H            H    &#34;                                  
88   CH.sub.2 C.sub.6 H.sub.5                                             
                     SC.sub.6 H.sub.3 Cl.sub.2 (2,5)                      
                                  H    blue                               
89   C.sub.6 H.sub.5 SCH.sub.3    H    &#34;                                  
90   CH.sub.3        H            OH   violet                             
91   CH.sub.3        H            CH.sub.3                                
                                       blue                               
92   CH.sub.3        Br           CH.sub.3                                
                                       blue                               
93   &#34;               SC.sub.6 H.sub.5                                     
                                  &#34;    green-                             
                                       ish                                
                                       blue                               
94   &#34;               SO.sub.2 C.sub.6 H.sub.5                             
                                  &#34;    blue                               
95   C.sub.2 H.sub.5 SCH.sub.3    &#34;    tur-                               
                                       quoise                             
96   &#34;               SO.sub.2 CH.sub.3                                    
                                  &#34;    blue                               
97   CH.sub.2 CH.sub.2 C.sub.6 H.sub.5                                    
                     COC.sub.6 H.sub.5                                    
                                  C.sub.2 H.sub.5                         
                                       &#34;                                  
98   CH.sub.2 CH.sub.2 COOCH.sub.3                                        
                     H            C.sub.2 H.sub.5                         
                                       &#34;                                  
99   &#34;               Br           &#34;    &#34;                                  
______________________________________                                    
 
    
     
                                           TABLE 3                                 
__________________________________________________________________________
Dyes                                                                      
 ##STR35##                                                                
Ex. R      R.sup.1  R.sup.3  Y    Hue                                     
__________________________________________________________________________
100 CH.sub.3                                                              
           SC.sub.2 H.sub.5                                               
                    SC.sub.2 H.sub.5                                      
                             CH.sub.3                                     
                                  blue                                    
101 &#34;      SC.sub.6 H.sub.4 CH.sub.3 (4)                                  
                    SC.sub.6 H.sub.4 CH.sub.3 (4)                         
                             CH.sub.3                                     
                                  &#34;                                       
102 &#34;      Cl       Cl       C.sub.2 H.sub.5                              
                                  reddish                                 
                                  violet                                  
103 &#34;      Br       NO.sub.2 &#34;    violet                                  
104 &#34;      SC.sub.6 H.sub.4 Cl(4)                                         
                    SC.sub.6 H.sub.4 Cl(4)                                
                             &#34;    blue                                    
105 C.sub.2 H.sub.5                                                       
           Br       Br       CH.sub.3                                     
                                  reddish                                 
                                  violet                                  
106 &#34;      SC.sub.6 H.sub.5                                               
                    SC.sub.6 H.sub.5                                      
                             &#34;    reddish                                 
                                  blue                                    
107 CH.sub.3                                                              
           Br       Br       H    red                                     
108 &#34;      SCH.sub.3                                                      
                    SCH.sub.3                                             
                             H    bluish                                  
                                  violet                                  
109 C.sub.2 H.sub.5                                                       
           Br       NO.sub.2 H    bluish red                              
110 C.sub.2 H.sub.5                                                       
           SC.sub.4 H.sub.9                                               
                    SC.sub.4 H.sub.9                                      
                             H    bluish                                  
                                  violet                                  
111 &#34;      SC.sub.6 H.sub.5                                               
                    SC.sub.6 H.sub.5                                      
                             H    bluish                                  
                                  violet                                  
112 &#34;      SC.sub.6 H.sub.4 CH.sub.3 (4)                                  
                    NO.sub.2 H    &#34;                                       
113 C.sub.3 H.sub.7                                                       
           Cl       Cl       H    red                                     
114 C.sub.4 H.sub.9                                                       
           SCH.sub.2 CH.sub.2 OH                                          
                    SCH.sub.2 CH.sub.2 OH                                 
                             H    bluish                                  
                                  violet                                  
115 C.sub.4 H.sub.9                                                       
           SC.sub.6 H.sub.4 OCH.sub.3 (4)                                 
                    SC.sub.6 H.sub.4 OCH.sub.3 (4)                        
                             H    &#34;                                       
116 CH.sub.2 C.sub.6 H.sub.5                                              
           Cl       Cl       H    red                                     
117 CH.sub.2 C.sub.6 H.sub.5                                              
           SC.sub.6 H.sub.4 Cl(4)                                         
                    SC.sub.6 H.sub.4 Cl(4)                                
                             H    bluish                                  
                                  violet                                  
118 C.sub.6 H.sub.5                                                       
           SC.sub.3 H.sub.7                                               
                    SC.sub.3 H.sub.7                                      
                             H    &#34;                                       
119 C.sub.6 H.sub.5                                                       
            SC.sub.6 H.sub.5                                              
                    SC.sub.6 H.sub.5                                      
                             H    &#34;                                       
120 &#34;      SC.sub.6 H.sub.3 Cl.sub.2 (2,5)                                
                    SC.sub.6 H.sub.3 Cl.sub.2 (2,5)                       
                             H    &#34;                                       
121 &#34;      C.sub.2 H.sub.5                                                
                    H        CH.sub.3                                     
                                  reddish                                 
                                  violet                                  
122 &#34;      NO.sub.2 Br       CH.sub.3                                     
                                  violet                                  
__________________________________________________________________________
 
    
     
                       TABLE 4                                                     
______________________________________                                    
Dyes                                                                      
 ##STR36##                                                                
Ex.  R               R.sup.1 = R.sup.3                                    
                              Y        Hue                                
______________________________________                                    
123  CH.sub.3        Cl       CH.sub.3 bluish                             
                                       violet                             
124  &#34;               SC.sub.6 H.sub.5                                     
                              &#34;        tur-                               
                                       quoise                             
125  CH.sub.2 CH.sub.2 CON(C.sub.2 H.sub.5).sub.2                         
                     Br       &#34;        bluish                             
                                       violet                             
126  C.sub.2 H.sub.5 Cl       OH       violet                             
127  CH.sub.2 CH.sub.2 C.sub.6 H.sub.5                                    
                     Cl       COOCH.sub.3                                 
                                       blue                               
128  CH.sub.2 CH.sub.2 C.sub.6 H.sub.5                                    
                     Br       &#34;        &#34;                                  
129  CH.sub.3        Cl       H        violet                             
130  C.sub.2 H.sub.5 SC.sub.2 H.sub.5                                     
                              H        blue                               
131  C.sub.2 H.sub.5 SC.sub.4 H.sub.9                                     
                              H        &#34;                                  
132  C.sub.2 H.sub.5 SC.sub.6 H.sub.5                                     
                              H        &#34;                                  
133  CH.sub.2 CH.sub.2 OH                                                 
                     Br       H        violet                             
134  (CH.sub.2).sub.3 OCH.sub.3                                           
                     SCH.sub.3                                            
                              H        blue                               
135  CH.sub.2 CH.sub.2 CN                                                 
                     &#34;        H        &#34;                                  
136  CH.sub.2 CH.sub.2 COOC.sub.3 H.sub.7                                 
                     SC.sub.6 H.sub.5                                     
                              H        &#34;                                  
137  CH.sub.2 CH.sub.2 CONHCH.sub.3                                       
                     Cl       H        violet                             
138  CH.sub.2 CH.sub.2 CON(C.sub.3 H.sub.7).sub.2                         
                     Br       H        &#34;                                  
139  CH.sub.2 CH.sub.2 C.sub.6 H.sub.5                                    
                     SC.sub.3 H.sub.7                                     
                              H        blue                               
______________________________________                                    
 
    
     
                                           TABLE 5                                 
__________________________________________________________________________
Dyes                                                                      
 ##STR37##                                                                
Ex-                                                                       
ample                                                                     
    R       R.sup.3  R.sup.4  Y   Hue                                     
__________________________________________________________________________
140 H       Cl       Cl       H   red                                     
141 H       SCH.sub.3                                                     
                     SCH.sub.3                                            
                              H   bluish violet                           
142 CH.sub.3                                                              
            Cl       Cl       H   red                                     
143 C.sub.2 H.sub.5                                                       
            Cl       SC.sub.6 H.sub.5                                     
                              H   violet                                  
144 &#34;       Cl       SC.sub.6 H.sub.4 OCH.sub.3 (4)                       
                              H   &#34;                                       
145 &#34;       Cl       SC.sub.6 H.sub.4 Cl(4)                               
                              H   &#34;                                       
146 &#34;       SC.sub.2 H.sub.5                                              
                     SC.sub.2 H.sub.5                                     
                              H   bluish violet                           
147 &#34;       SC.sub.6 H.sub.5                                              
                     H        &#34;                                           
148 CH.sub.2 CH.sub.2 OH                                                  
            Cl       Cl       H   red                                     
149 CH.sub.3                                                              
            Cl       Cl       CH.sub.3                                    
                                  reddish violet                          
150 CH.sub.3                                                              
            SCH.sub.2 CH.sub.2 OH                                         
                     SCH.sub.2 CH.sub.2 OH                                
                              &#34;   blue                                    
151 CH.sub.3                                                              
            Cl       SC.sub.6 H.sub.5                                     
                              &#34;   &#34;                                       
152 CH.sub.3                                                              
            H        OCH.sub.3                                            
                              CH.sub.3                                    
                                  reddish violet                          
__________________________________________________________________________
 
    
     EXAMPLE 153 
     160 parts of phosphorus oxychloride are added dropwise at 70° C to a mixture of 800 parts of butyrolactone, 169 parts of naphtholactam and 188 parts of 1-ethyl-2-hydroxypyrid-6-one-3-carboxamide. 
     The mixture is stirred for 8 hours at 70° C, 400 parts of methanol and 400 parts of water are added successively and the whole is allowed to cool. After filtering off, washing and drying the product, 276 parts of the dye ##STR38## are obtained. 
     If the condensation is carried out at 70° C or with a substantial excess of phosphorus oxychloride, the reaction product contains substantial amounts of the dye described in Example 1. The dye of Example 153 is also obtained by hydrolyzing the dye 1, for example with 91% strength sulfuric acid at 85° C (more concentrated sulfuric acid leads to sulfonation of the naphthalene ring). The dye has very similar tinctorial properties to those of the dye described in Example 1. 
     
                                           TABLE 6                                 
__________________________________________________________________________
Dyes                                                                      
 ##STR39##                                                                
Ex-                                                                       
ample                                                                     
    R.sup.1     R.sup.2                                                   
                  R.sup.3     R.sup.4                                     
                                   R.sup.5                                
                                     R       Hue                          
__________________________________________________________________________
154 H           H H           H    H CH.sub.3                             
                                             yellowish red                
155 H           H H           H    H (CH.sub.2).sub.3 OCH.sub.3           
                                             yellowish red                
156 H           H Cl          H    H C.sub.4 H.sub.9                      
                                             red                          
157 H           H Br          H    H C.sub.2 H.sub.5                      
                                             red                          
158 Br          H Br          H    H C.sub.2 H.sub.5                      
                                             red                          
159 H           Cl                                                        
                  Cl          Cl   Cl                                     
                                     C.sub.2 H.sub.5                      
                                             red                          
160 H           H SC.sub.6 H.sub.5                                        
                              H    H C.sub.2 H.sub.5                      
                                             violet                       
161 H           H SC.sub.6 H.sub.5                                        
                              SC.sub.6 H.sub.5                            
                                   H C.sub.2 H.sub.5                      
                                             violet                       
162 H           H COC.sub.6 H.sub.5                                       
                              H    H C.sub.2 H.sub.5                      
                                             red                          
163 H           H COCH.sub.2 CH.sub.2 Cl                                  
                              H    H CH.sub.3                             
                                             red                          
164 H           H SO.sub.2 CH.sub.3                                       
                              H    H C.sub.2 H.sub.5                      
                                             bluish red                   
165 H           H NO.sub.2    H    H C.sub.2 H.sub.5                      
                                             reddishviolet                
166 H           H                                                         
                   ##STR40##  H    H C.sub.2 H.sub.5                      
                                             red                          
167 H           H SO.sub.2 N(CH.sub.3).sub.2                              
                              H    H C.sub.2 H.sub.5                      
                                             red                          
168 SC.sub.6 H.sub.5                                                      
                H SC.sub.6 H.sub.5                                        
                              H    H C.sub.2 H.sub.5                      
                                             bluish violet                
169                                                                       
     ##STR41##  H                                                         
                   ##STR42##  H    H C.sub.2 H.sub.5                      
                                             bluish violet                
170 H           H SO.sub.2 N(C.sub.3 H.sub.7).sub.2                       
                              H    H C.sub.2 H.sub.5                      
                                             red                          
171 H           H                                                         
                   ##STR43##  H    H C.sub.2 H.sub.5                      
                                             red                          
172 H           H                                                         
                   ##STR44##  H    H C.sub.2 H.sub.5                      
                                             red                          
173 H           H SO.sub.2 NHC.sub.6 H.sub.5                              
                              H    H C.sub.2 H.sub.5                      
                                             red                          
174 H           H                                                         
                   ##STR45##  H    H C.sub.2 H.sub.5                      
                                             red                          
__________________________________________________________________________
 
    
     EXAMPLE 175 
     200 parts of phosphorus oxychloride are added dropwise, at 80° C, to a mixture of 1,200 parts of ethylene glycol dimethyl ether, 247 parts of 4-methylsulfonyl-naphtholactam and 264 parts of N,N&#39;-dipropyl-2-hydroxypyrid-6-one-3,4-dicarboximide. Dark crystals separate out from the solution. The mixture is boiled for 2 hours under reflux and 800 parts of methanol are added whilst it is cooling. After it has cooled, the product is filtered off, washed with methanol and dried. 401 parts of the dye having the structure ##STR46## are obtained in the form of dark crystals having a metallic gloss. The dye may be used to dye polyesters, from an aqueous bath, in brilliant neutral blue hues having good fastness properties. 
     
                                           TABLE 7                                 
__________________________________________________________________________
 ##STR47##                                                                
Example                                                                   
     R.sup.1                                                              
        R.sup.2                                                           
           R.sup.3      R.sup.4                                           
                           R.sup.5                                        
                              R        Hue                                
__________________________________________________________________________
176  H  H  H            H  H                                              
                               ##STR48##                                  
                                       violet                             
177  H  H  H            H  H  CH.sub.2 CH.sub.2 C.sub.6 H.sub.5           
                                       bluish violet                      
178  Cl H  Cl           H  H  C.sub.4 H.sub.9 (iso)                       
                                       reddish blue                       
179  Cl H  Cl           Cl Cl CH.sub.2 CH.sub.2 CN                        
                                       reddish blue                       
180  H  H  Br           H  H  (CH.sub.2).sub.3 OCH.sub.3                  
                                       bluish violet                      
181  H  H  Br           H  H                                              
                               ##STR49##                                  
                                       bluish violet                      
182  H  H  H            H  H  C.sub.6 H.sub.5                             
                                       reddish blue                       
182  H  H  C.sub.2 H.sub.5 SO.sub.2                                       
                        H  H  C.sub.2 H.sub.5                             
                                       blue                               
183  H  H  CH.sub.3 C.sub.6 H.sub.4 SO.sub.2                              
                        H  H  C.sub.4 H.sub.9                             
                                       blue                               
184  H  H  CH.sub.3 CO  H  H  C.sub.5 H.sub.11                            
                                       reddish blue                       
185  H  H  ClCH.sub.2 CO                                                  
                        H  H  C.sub.3 H.sub.7 (iso)                       
                                       reddish blue                       
186  H  H  C.sub.2 H.sub.5 CO                                             
                        H  H  C.sub.2 H.sub.5                             
                                       reddish blue                       
187  H  H                                                                 
            ##STR50##   H  H  C.sub.2 H.sub.5                             
                                       reddish blue                       
188  H  H                                                                 
            ##STR51##   H  H  C.sub.2 H.sub.5                             
                                       reddish blue                       
189  H  H                                                                 
            ##STR52##   H  H  C.sub.2 H.sub.5                             
                                       reddish blue                       
190  H  H                                                                 
            ##STR53##   H  H  C.sub.2 H.sub.4                             
                                       bluish violet                      
192  H  H                                                                 
            ##STR54##   H  H  C.sub.2 H.sub.5                             
                                       bluish violet                      
193  H  H                                                                 
            ##STR55##   H  H  C.sub.2 H.sub.5                             
                                       bluish violet                      
194  H  H                                                                 
            ##STR56##   H  H  C.sub.2 H.sub.5                             
                                       bluish violet                      
195  H  H  CH.sub.3 NHCONH                                                
                        H  H  C.sub.2 H.sub.5                             
                                       bluish violet                      
196  H  H  NO.sub.2     H  H  C.sub.3 H.sub.7                             
                                       blue                               
__________________________________________________________________________
 
    
     EXAMPLE 197 
     169 parts of naphtholactam and 227 parts of ##STR57## are introduced into 1,200 parts of dimethyl glycol and the mixture is stirred at 70° C. 165 parts of phosphorus oxychloride are added dropwise in the course of one hour and stirring is continued for 8 hours. After the mixture has cooled, it is filtered and the filter cake is dispersed in dilute ammonia. After again filtering off, and washing the product with water and drying it, 287 parts of the dye having the structure. ##STR58## are obtained; it may be used to dye polyesters, from an aqueous bath, in light-fast violet hues. Dyes with B ═ CH 3  or OCH 3 , which have been prepared similarly, exhibit a hue somewhat shifted toward blue. 
     
                       TABLE 8                                                     
______________________________________                                    
 ##STR59##                                                                
Ex.  R              R.sup.3       B     Hue                               
______________________________________                                    
198  H              Br            H     vio-                              
                                        let                               
199  H              OCH.sub.3     H     blu-                              
                                        ish                               
                                        vio-                              
                                        let                               
200  H              CH.sub.3      H     vio-                              
                                        let                               
201  H              NO.sub.2      H     blu-                              
                                        ish                               
                                        vio-                              
                                        let                               
202  H              SC.sub.6 H.sub.5                                      
                                  H     blue                              
203  H              SC.sub.6 H.sub.4 CH.sub.3 (4&#39;)                        
                                  H     blue                              
204  H              SC.sub.6 H.sub.4 OCH.sub.3 (4&#39;)                       
                                  H     blue                              
205  CH.sub.3       H             H     blue                              
206  CH.sub.2 CH.sub.2 CN                                                 
                    H             H     blue                              
207  CH.sub.2 CH.sub.2 COOC.sub.2 H.sub.5                                 
                    H             H     blue                              
208  H              C1            OCH.sub.3                               
                                        blue                              
209  H              H             C1    vio-                              
                                        let                               
______________________________________                                    
 
    
     EXAMPLE 210 
     169 parts of naphtholactam and 309 parts of a compound having the structure. ##STR60## are introduced into 1,500 parts of ethylene glycol dimethyl ether, and 185 parts of phosphorus oxychloride are added at 75° C. After boiling the mixture for 4 hours, 500 parts of ethanol are added dropwise and the batch is allowed to cool. 500 parts of water are then added dropwise and the product is filtered off and washed with dilute ammonia solution and with water. After drying, 344 parts of the dye having the structure ##STR61## are obtained. This dye may be used to dye polyesters from an aqueous bath, giving slightly greenish blue dyeings with good fastness properties. Dyes of the same hue are obtained if the butyl group is replaced by other alkyl radicals, including substituted or branched radicals. Dues with B = CH 3  or OCH 3  exhibit a hue shifted somewhat more toward green. 
     The following are further dyes which have been prepared in accordance with the methods of Examples 1 - 10: ##STR62## 
     EXAMPLE 219 
     169 parts of naphtholactam and 210 parts of N,N&#39;-diethyl2-hydroxypyrid-6-one-3-carboxamide are introduced into 750 parts of butyrolactone and the mixture is stirred at 70° C. 175 parts of phosphorus oxychloride are added dropwise, whereupon the reaction mixture assumes a deep red color. The mixture is stirred for a further 6 hours at 70° C, after which 250 parts of methanol and 250 parts of water are successively added dropwise. After the mixture was cooled, the crystals are filtered off and washed with 50% strength methanol. After drying, 309 parts of the dye having the structure ##STR63## are obtained in the form of a red crystal powder. The dye may be used to dye polyester fibers and fabrics, from an aqueous bath, in brilliant red hues having very good fastness properties, especially excellent light fastness. 
     EXAMPLE 220 
     277 parts of 4-phenylmercaptonaphtholactam and 182 parts of N,N&#39;-dimethyl-2-hydroxypyrid-6-one-3-carboxamide are introduced into 1,000 parts of dehydrated chlorobenzene. 180 parts of phosphorus oxychloride are added dropwise at 80° C, whilst stirring, and the mixture is then kept for 4 hours at 80° C. The heating bath is then temporarily removed and 1,000 parts of methanol are carefully added to the reaction mixture. The batch is then boiled for half an hour under reflux and is allowed to cool, and the product is filtered off. 
     After drying, 336 parts of the dye having the structure ##STR64## are obtained in the form of a dark crystal powder. The dye may be used to dye polyesters from an aqueous bath, giving light-fast violet hues. 
     The pyridone derivative is obtained as follows: 
     72 parts of sodium methylate are introduced into a mixture of 75 parts of ethyl formate and 120 parts of ethyl acetate at -10° to 0° C, whilst stirring. The mixture is left to stand overnight at room temperature, the colorless crystal slurry is then dissolved by pouring 750 parts by volume of absolute ethanol over it, and 130 parts of malonic acid bis-methylamide are introduced. The reaction mixture is now boiled for 8 hours under reflux, in the course of which it gradually solidfies to a crystal slurry. Excess 10% strength hydrochloric acid is then added and ethanol/water is distilled off until the internal temperature has reached 100° C. On cooling, colorless crystals separate out from the clear solution; they are filtered off and dried. Yield: 123 parts of 1-methyl-2-hydroxypyrid6-one-3-carboxylic acid methylamide of melting point 206° - 208° C. 
     Analysis: C 8  H 10  N 2  O 3  (182) calculated C 52.8; H 5.5; N 15.4; O 26.4; found 52.8; 5.5; 15.5; 26.4. 
     
                                           TABLE 9                                 
__________________________________________________________________________
 ##STR65##                                                                
Example                                                                   
     R.sup.3           A.sup.1   Hue                                      
__________________________________________________________________________
221  H               CH.sub.3    red                                      
222  H               C.sub.3 H.sub.7 (n)                                  
                                 red                                      
223  H               C.sub.3 H.sub.7 (iso)                                
                                 red                                      
224  H               C.sub.4 H.sub.9 (n)                                  
                                 red                                      
225  H               C.sub.4 H.sub.9 (sec)                                
                                 red                                      
226  H                                                                    
                      ##STR66##  red                                      
227  H               CH.sub.2 CH.sub.2 OH                                 
                                 red                                      
228  H               CH.sub.2 CH.sub.2 OCOCH.sub.3                        
                                 red                                      
229  H               CH.sub.2 CH.sub.2 OCOC.sub.6 H.sub.5                 
                                 red                                      
230  H               CH.sub.2 CH.sub.2 CN                                 
                                 red                                      
231  H               CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                 
                                 red                                      
232  H               CH.sub.2 CH.sub.2 CH.sub.2 OC.sub.3 H.sub.7          
                                 red                                      
233  H               CH.sub.2 C.sub.6 H.sub.5                             
                                 red                                      
234  H               CH.sub.2 CH.sub.2 C.sub.6 H.sub.5                    
                                 red                                      
235  H               CH.sub.2 CH.sub.2 CH.sub.2 OC.sub.6 H.sub.5          
                                 red                                      
236  H                                                                    
                      ##STR67##  red                                      
237  H               CH.sub.2 CH(C.sub.6 H.sub.5)CH.sub.3                 
                                 red                                      
238  H               C.sub.6 H.sub.5                                      
                                 red                                      
239  H                                                                    
                      ##STR68##  red                                      
240  H                                                                    
                      ##STR69##  red                                      
241  H                                                                    
                      ##STR70##  bluish red                               
242  Cl              C.sub.2 H.sub.5                                      
                                 red                                      
243  Br              C.sub.2 H.sub.5                                      
                                 bluish red                               
244  Br              C.sub.3 H.sub.7 (iso)                                
                                 bluish red                               
245  Br              C.sub.4 H.sub.9 (n)                                  
                                 bluish red                               
246  CH.sub.3        CH.sub.3    red                                      
247  OC.sub.2 H.sub.5                                                     
                     CH.sub.3    bluish red                               
248  COCH.sub.3      C.sub.2 H.sub.5                                      
                                 red                                      
249  COCH.sub.3      C.sub.3 H.sub.7                                      
                                 red                                      
250  COC.sub.2 H.sub.5                                                    
                     C.sub.2 H.sub.5                                      
                                 red                                      
251  COCH.sub.2 Cl   C.sub.2 H.sub.5                                      
                                 red                                      
252  COCH.sub.2 CH.sub.2 Cl                                               
                     C.sub.2 H.sub.5                                      
                                 red                                      
253  COC.sub.6 H.sub.5                                                    
                     CH.sub.3    red                                      
254  COC.sub.6 H.sub.5                                                    
                     C.sub.3 H.sub.7                                      
                                 red                                      
255   COC.sub.6 H.sub.5                                                   
                     C.sub.4 H.sub.9 (sec)                                
                                 red                                      
256                                                                       
      ##STR71##      CH.sub.3    red                                      
257                                                                       
      ##STR72##      CH.sub.3    red                                      
258                                                                       
      ##STR73##      CH.sub.3    red                                      
259                                                                       
      ##STR74##      CH.sub.3    red                                      
260                                                                       
      ##STR75##      CH.sub.3    red                                      
261  SO.sub.2 CH.sub.3                                                    
                      CH.sub.3   bluish red                               
262  SO.sub.2 C.sub.2 H.sub.5                                             
                     CH.sub.3    bluish red                               
263  SO.sub.2 CH.sub.2 CHCH.sub.2                                         
                     CH.sub.3    bluish red                               
264  SO.sub.2 NHC.sub.2 H.sub.5                                           
                     CH.sub.3    red                                      
265  SO.sub.2 NH(CH.sub.2).sub.3 OC.sub.2 H.sub.5                         
                     CH.sub.3    red                                      
266                                                                       
      ##STR76##      CH.sub.3    red                                      
267  SO.sub.2 NH(CH.sub.2).sub.3 OC.sub.4 H.sub.9                         
                     C.sub.2 H.sub.5                                      
                                 red                                      
268  SO.sub.2 N(CH.sub.3).sub.2                                           
                     C.sub.4 H.sub.9 (n)                                  
                                 red                                      
269                                                                       
      ##STR77##      CH.sub.3    red                                      
270  SO.sub.2 N(C.sub.4 H.sub.9).sub.2                                    
                     C.sub.2 H.sub.5                                      
                                 red                                      
271  SO.sub.2 NHCl.sub.6 H.sub.5                                          
                     C.sub.2 H.sub.5                                      
                                 red                                      
272                                                                       
      ##STR78##      CH.sub.3    red                                      
273                                                                       
      ##STR79##      C.sub.2 H.sub.5                                      
                                 red                                      
274                                                                       
      ##STR80##      C.sub.3 H.sub.7 (iso)                                
                                 red                                      
275  SO.sub.2 NHCH.sub.2 C.sub.6 H.sub.5                                  
                     C.sub.2 H.sub.5                                      
                                 red                                      
276  SO.sub.2 NH(CH.sub.2).sub.3 O(CH.sub.2).sub.4 OH                     
                     CH.sub.3    red                                      
277  SO.sub.2 NH(CH.sub.2).sub.3 O(CH.sub.3).sub.2 OC.sub.6 H.sub.5       
                      CH.sub.3   red                                      
278                                                                       
      ##STR81##      C.sub.4 H.sub.9                                      
                                 red                                      
279                                                                       
      ##STR82##      C.sub.4 H.sub.9 (tertiary)                           
                                 red                                      
280                                                                       
      ##STR83##      C.sub.3 H.sub.7 (n)                                  
                                 red                                      
281                                                                       
      ##STR84##      C.sub.2 H.sub.5                                      
                                 red                                      
282  SC.sub.2 H.sub.5                                                     
                     CH.sub.3    violet                                   
283  SCH.sub.2 CH.sub.2 OH                                                
                     CH.sub.3    violet                                   
284  SC.sub.4 H.sub.9                                                     
                     C.sub.2 H.sub.5                                      
                                 violet                                   
285  SC.sub.6 H.sub.5                                                     
                     C.sub.2 H.sub.5                                      
                                 violet                                   
286  SC.sub.6 H.sub.5                                                     
                     C.sub.3 H.sub.7 (iso)                                
                                 violet                                   
287                                                                       
      ##STR85##      CH.sub.3    violet                                   
288                                                                       
      ##STR86##      CH.sub.3    violet                                   
289                                                                       
      ##STR87##      CH.sub.3    violet                                   
290                                                                       
      ##STR88##      CH.sub.3    violet                                   
291                                                                       
      ##STR89##      CH.sub.3    violet                                   
292                                                                       
      ##STR90##      C.sub.2 H.sub.5                                      
                                 violet                                   
293                                                                       
      ##STR91##      CH.sub.3    violet                                   
294                                                                       
      ##STR92##      CH.sub.3    violet                                   
295  SO.sub.2 C.sub.6 H.sub.5                                             
                     C.sub.2 H.sub.5                                      
                                 bluish red                               
296                                                                       
      ##STR93##      C.sub.2 H.sub.5                                      
                                 bluish red                               
297  NO.sub.2        CH.sub.3    bluish red                               
298  NO.sub.2        C.sub.2 H.sub.5                                      
                                 bluish red                               
299  NO.sub.2        C.sub.3 H.sub.7                                      
                                 bluish red                               
300  NO.sub.2        C.sub.3 H.sub.7 (iso)                                
                                 bluish red                               
301  NHCOCH.sub.3    C.sub.2 H.sub.5                                      
                                 reddish violet                           
302  NHCOC.sub.2 H.sub.5                                                  
                     C.sub.2 H.sub.5                                      
                                 reddish violet                           
303  NHCONH.sub.2    C.sub.2 H.sub.5                                      
                                 reddish violet                           
304  NHCOC.sub.6 H.sub.5                                                  
                     C.sub.3 H.sub.7                                      
                                 reddish violet                           
305  NHSO.sub.2 CH.sub.3                                                  
                     C.sub.2 H.sub. 5                                     
                                 reddish violet                           
306  NHSO.sub.2 C.sub.4 H.sub.9                                           
                     CH.sub.3    reddish violet                           
307                                                                       
      ##STR94##      C.sub.2 H.sub.5                                      
                                 reddish violet                           
308                                                                       
      ##STR95##      C.sub.2 H.sub.5                                      
                                 reddish violet                           
__________________________________________________________________________
 
    
     EXAMPLE 309 
     190 parts of phosphorus oxychloride are added in the course of one hour to a mixture of 1,200 parts of butyrolactone, 259 parts of N-benzyl-naphtholactam and 266 parts of N,N&#39;-dibutyl-2-hydroxypyrid6-one-3-carboxamide at 100° C and the batch is kept at this temperature for 2 hours. The heating is then discontinued and 800 parts of methanol are added dropwise at a rate such that the reaction mixture comes to the boil. In the course thereof, the dark melt turns to a crystal suspension, which is filtered after it has cooled. After washing the product with methanol and drying, 355 parts of the dye having the structure ##STR96## are obtained. When worked into thermoplastics, the dye gives violet hues having very good lightfastness. Tinctorially equivalent dyes are obtained with N-phenylnaphtholactam and N-phenylethylnaphtholactam. 
     
                                           TABLE 10                                
__________________________________________________________________________
Dyes                                                                      
 ##STR97##                                                                
Example                                                                   
      R           R.sup.3  A   A.sup.1                                    
                                    Hue                                   
__________________________________________________________________________
310   CH.sub.3    H        H   C.sub.2 H.sub.5                            
                                    violet                                
311   CH.sub.3    H        CH.sub.3                                       
                               CH.sub.3                                   
                                    blue                                  
312   C.sub.2 H.sub.5                                                     
                  Br       H   CH.sub.3                                   
                                    violet                                
313   CH.sub.3    H        C.sub.4 H.sub.9                                
                               CH.sub.3                                   
                                    blue                                  
314   H           COC.sub.6 H.sub.5                                       
                           CH.sub.3                                       
                               CH.sub.3                                   
                                    reddish violet                        
315   H           H        OH  C.sub.2 H.sub.5                            
                                    orange                                
316   H           SO.sub.2 CH.sub.3                                       
                           OH  C.sub.3 H.sub.7                            
                                    yellowish red                         
317   H           SC.sub.6 H.sub.5                                        
                           OH  CH.sub.3                                   
                                    dull bluish                           
                                    red                                   
318   H           SO.sub.2 N(C.sub.2 H.sub.5).sub.2                       
                           OH  C.sub.2 H.sub.5                            
                                    yellowish red                         
319   CH.sub.2 CH.sub.2 CN                                                
                  H        OH  CH.sub.3                                   
                                    violet                                
320   C.sub.4 H.sub.9                                                     
                  COC.sub.6 H.sub.5                                       
                           OH  C.sub.2 H.sub.5                            
                                    violet                                
321   C.sub.2 H.sub.5                                                     
                  SC.sub.6 H.sub.5                                        
                           OH  CH.sub.3                                   
                                    reddish blue                          
322   CH.sub.2 C.sub.6 H.sub.5                                            
                  H        OH  C.sub.4 H.sub.9                            
                                    violet                                
323   (CH.sub.2).sub.2 COOCH.sub.3                                        
                  Cl       H   C.sub.2 H.sub.5                            
                                    violet                                
324   (CH.sub.2).sub.2 CON(CH.sub.3).sub.2                                
                  H        H   CH.sub.3                                   
                                    violet                                
325   CH.sub.3    SC.sub.6 H.sub.5                                        
                           H   CH.sub.3                                   
                                    reddish blue                          
326   (CH.sub.2).sub.3 OCH.sub.3                                          
                  Br       H   CH.sub.3                                   
                                    violet                                
__________________________________________________________________________
 
    
     
                                           TABLE 11                                
__________________________________________________________________________
Dyes                                                                      
 ##STR98##                                                                
Example                                                                   
      R.sup.1     R.sup.3   A   A.sup.1                                   
                                     Hue                                  
__________________________________________________________________________
327   Cl          Cl        H   C.sub.2 H.sub.5                           
                                     red                                  
328   Cl          NO.sub.2  H   C.sub.2 H.sub.5                           
                                     red                                  
329   Br          Br        H   C.sub.3 H.sub.7                           
                                     bluish red                           
330   Br          NO.sub.2  H   CH.sub.3                                  
                                     bluish red                           
331   NO.sub.2    Br        H   C.sub.2 H.sub.5                           
                                     red                                  
332   SCH.sub.3   SCH.sub.3 H   C.sub.2 H.sub.5                           
                                     bluish violet                        
333   SCH.sub.2 CH.sub.2 OH                                               
                  SCH.sub.2 CH.sub.2 OH                                   
                            H   CH.sub.3                                  
                                     bluish violet                        
334   SC.sub.6 H.sub.5                                                    
                  SC.sub.6 H.sub.5                                        
                            H   C.sub.2 H.sub.5                           
                                     bluish violet                        
335                                                                       
       ##STR99##                                                          
                   ##STR100##                                             
                            H   CH.sub.3                                  
                                     violet                               
336                                                                       
       ##STR101##                                                         
                   ##STR102##                                             
                            H   C.sub.2 H.sub.5                           
                                     bluish violet                        
337   Br          Br        OH  C.sub.2 H.sub.5                           
                                     reddish orange                       
338   SC.sub.6 H.sub.5                                                    
                  SC.sub.6 H.sub.5                                        
                            OH  CH.sub.3                                  
                                     violet                               
339                                                                       
       ##STR103##                                                         
                   ##STR104##                                             
                            OH  C.sub.2 H.sub.5                           
                                     violet                               
340   Cl          Cl        CH.sub.3                                      
                                CH.sub.3                                  
                                     reddish violet                       
341   SC.sub.6 H.sub.5                                                    
                  SC.sub.6 H.sub.5                                        
                            CH.sub.3                                      
                                CH.sub.3                                  
                                     blue                                 
__________________________________________________________________________
 
    
     
                                           TABLE 12                                
__________________________________________________________________________
Dyes                                                                      
 ##STR105##                                                               
Example                                                                   
      R.sup.3     R.sup.4   A   A.sup.1                                   
                                     Hue                                  
__________________________________________________________________________
342    Cl         Cl        H   C.sub.2 H.sub.5                           
                                     red                                  
343   Cl          Cl        H   C.sub.3 H.sub.7                           
                                (iso)                                     
                                     red                                  
344   SC.sub.2 H.sub.5                                                    
                  SC.sub.2 H.sub.5                                        
                            H   CH.sub.3                                  
                                     bluish violet                        
345   Cl          SC.sub.6 H.sub.5                                        
                            H   C.sub.2 H.sub.5                           
                                     reddish violet                       
346   Cl          SC.sub.6 H.sub.5                                        
                            H   C.sub.4 H.sub.9                           
                                     reddish violet                       
347   Cl                                                                  
                   ##STR106##                                             
                            H   C.sub.2 H.sub.5                           
                                     reddish violet                       
348   Cl                                                                  
                   ##STR107##                                             
                            H   C.sub.2 H.sub.5                           
                                     reddish violet                       
349   H            OCH.sub.3                                              
                            H   CH.sub.3                                  
                                     red                                  
350   Cl          Cl        OH  C.sub.2 H.sub.5                           
                                     orange                               
351   Cl                                                                  
                   ##STR108##                                             
                            OH  C.sub.2 H.sub.5                           
                                     red                                  
352   SC.sub.6 H.sub.5                                                    
                  SC.sub.6 H.sub.5                                        
                            OH  C.sub.2 H.sub.5                           
                                     reddish violet                       
353   Cl          Cl        CH.sub.3                                      
                                CH.sub.3                                  
                                     reddish violet                       
354   SCH.sub.3   SCH.sub.3 CH.sub.3                                      
                                C.sub.2 H.sub.5                           
                                     blue                                 
355                                                                       
       ##STR109##                                                         
                   ##STR110##                                             
                            CH.sub.3                                      
                                CH.sub.3                                  
                                     blue                                 
__________________________________________________________________________
 
    
     EXAMPLE 356 
     307 parts of 3,4,5,6-tetrachloronaphtholactam and 250 parts of N,N&#39;-diisopropyl-2-hydroxypyrid-6-one are introduced into 1,300 parts of dehydrated nitrobenzene and the mixture is stirred at 90° C. 195 parts of phosphorus oxychloride are added dropwise and stirring is continued for 4 hours at 99° - 100° C. The excess phosphorus oxychloride is then decomposed by adding 700 parts of ethanol and the mixture is boiled up briefly and allowed to cool. After filtering off, washing the product with ethanol and drying it, 411 parts of the dye having the structure ##STR111## are obtained. In polystyrene, this dye gives heat-stable and very light-fast brilliant red colorations. The dye with R ═ H and A ═ OH, prepared similarly, colors polystyrene reddish orange whilst the dye with R ═ --CH 3  and A ═ H colors polystyrene violet. 
     EXAMPLE 357 
     271 parts of 4,5-benzoylenenaphtholactam (prepared as described in C.A. 53, 9183 g) and 300 parts of N,N&#39;-bis-methoxypropyl-2-hydroxypyrid-6-one-3-carboxamide are introduced into 1,200 parts of dehydrated dichlorobenzene and the mixture is stirred at 100° C. 200 parts of phosphorus oxychloride was added dropwise and stirring is continued for 4 hours at 110° C. When the mixture has cooled, 800 parts of methanol are added and the product is filtered off and washed with methanol. After it has been dried, 443 parts of the dye of the formula ##STR112## are obtained. When worked into thermoplastics, the dye gives reddish violet colorations distinguished by very good lightfastness. 
     EXAMPLE 358 
     275 parts of the compound ##STR113## and 266 parts of N,N&#39;-bis-isobutyl-2-hydroxypyrid-6-one-3-carboxamide are introduced into 1,500 parts of butyrolactone. The mixture is stirred at 90° C and 200 parts of phosphorus oxychloride are added in the course of 2 hours. Stirring is continued for 10 hours at 90° C and 1,000 parts of methanol are then added dropwise, whilst discontinuing the heating. After filtering off, washing the product with methanol and drying it, 336 parts of the dye having the structure ##STR114## are obtained. This dye, worked into polystyrene or other thermoplastics, gives light-fast greenish blue colorations. 
     EXAMPLE 359 
     250 parts of phosphorus oxychloride are added in the course of 2 hours to a mixture of 1,400 parts of ethylene glycol dimethyl ether, 169 parts of naphtholactam and 299 parts of the compound ##STR115## whilst stirring at 70° C. The mixture is then stirred for a further 6 hours at 70° C, after which 1,000 parts of methanol are added. When the mixture has cooled, it is filtered and the filter residue is dispersed in dilute ammonia. After again filtering off, washing the product with water and drying it, 297 parts of the dye ##STR116## are obtained. This dye may be used to dye polyester fibers and fabrics from an aqueous bath, giving strong brilliant violet dyeings distinguished by good lightfastness and fastness to thermofixation. Dyes with equivalent tinctorial properties are obtained by varying A 1  from methyl to 2-ethylhexyl, the optimum affinity being found with a total of from 4 to 5 carbon atoms. 
     The condensation products may be prepared by, for example, the following method: 
     77 parts of sodium methylate are introduced into a mixture of 80 parts of ethyl formate and 140 parts of ethyl acetate whilst cooling at from -20° to 0° C. After being left to stand overnight, the colorless slurry of the sodium salt of formylethyl acetate is dissolved by adding 400 parts by volume of ethylene glycol monomethyl ether, and 189 parts of benzimidazolyl-2-aceto-N-methylamide are added to the solution. The mixture is boiled for 4 hours under reflux, 600 parts by volume of water are added and the batch is acidified with concentrated hydrochloric acid. The reaction mixture is boiled for 1/2 hour, sodium acetate is added until the mixture reacts neutral, and the product is filtered off. After washing the product with warm water and drying it, 208 parts of the compound of the formula ##STR117## are obtained. The melting point of a sample recrystallized from dimethylformamide is 321° C (with decomposition). 
     Analysis: C 13  H 11  N 3  O 2  (241); calculated C 64.8 H 4.6 N 17.4 O 13.3; found 64.5 4.9 17.3 13.7. 
     
                                           TABLE 13                                
__________________________________________________________________________
Dyes                                                                      
 ##STR118##                                                               
Example                                                                   
     R       R.sup.3     A     A.sup.1 Y        Hue                       
__________________________________________________________________________
360  C.sub.2 H.sub.5                                                      
             H           H     C.sub.4 H.sub.9                            
                                       H        blue                      
361  H       Br          H     C.sub.2 H.sub.5                            
                                       H        violet                    
362  H       SO.sub.2 CH.sub.3                                            
                         H     (CH.sub.2).sub.3 OC.sub.2 H.sub.5          
                                       H        bluish                    
                                                violet                    
363  H       H           H     C.sub.3 H.sub.7                            
                                       Cl       violet                    
364  H       H           H     C.sub.3 H.sub.7                            
                                       CH.sub.3 violet                    
365  H       Cl          H     (CH.sub.2).sub.3 OCH.sub.3                 
                                       OCH.sub.3                          
                                                bluish                    
                                                violet                    
366  H       NO.sub.2    H     (CH.sub.2).sub.3 OCH.sub.3                 
                                       H        blue                      
367  H       SC.sub.6 H.sub.5                                             
                         H     C.sub.4 H.sub.9                            
                                       H        blue                      
368  H       SO.sub.2 N(C.sub.4 H.sub.9).sub.2                            
                         H     CH.sub.3                                   
                                       H        bluish                    
                                                violet                    
369  H                                                                    
              ##STR119## H     C.sub.2 H.sub.5                            
                                       H        bluish violet             
370  H       COC.sub.2 H.sub.5                                            
                         H     C.sub.4 H.sub.9                            
                                       H        bluish                    
                                                violet                    
371  H       H           CH.sub.3                                         
                               CH.sub.3                                   
                                       H        blue                      
372  H       Br          CH.sub.3                                         
                               CH.sub.3                                   
                                       H        blue                      
373  H       H           OH    C.sub.2 H.sub.5                            
                                       H        reddish                   
                                                violet                    
374  CH.sub.3                                                             
             H           OH    CH.sub.3                                   
                                       H        bluish                    
                                                violet                    
375  CH.sub.2 CH.sub.2 CN                                                 
             Br          H     CH.sub.3                                   
                                       H        blue                      
376  CH.sub.2 C.sub.6 H.sub.5                                             
             H           H     CH.sub.3                                   
                                       H        blue                      
377  H       H           H     C.sub.3 H.sub.7                            
                                       CON(CH.sub.3).sub.2                
                                                bluish                    
                                                violet                    
378  H       Cl          H     C.sub.2 H.sub.5                            
                                       CON(C.sub.4 H.sub.9).sub.2         
                                                bluish                    
                                                violet                    
379  H       H           H     C.sub.2 H.sub.5                            
                                       COOCH.sub. 3                       
                                                bluish                    
                                                violet                    
__________________________________________________________________________