Patent Publication Number: US-4652633-A

Title: Sulfo-containing halophenylazodiamino, cyano pyridine compounds

Description:
The present invention relates to compounds which, in the form of the free acids, are of the general formula I ##STR3## where X is fluorine, chlorine, bromine, methyl, trifluoromethyl, C 1  -C 4  -alkylsulfonyl, arylsulfonyl, acetyl or benzoyl, Y is hydrogen, fluorine, chlorine, bromine, sulfamyl, C 1  -C 4  -mono- or -dialkylsulfamyl, C 1  -C 4  -alkylsulfonyl, methyl or trifluoromethyl, Y 1  is hydrogen, hydroxysulfonyl, methyl or chlorine, Y 2  is hydrogen or hydroxysulfonyl and K is a radical of the formula ##STR4## either Y 1  or Y 2  being hydroxysulfonyl, and T is cyano or methylsulfonyl, R is hydrogen or C 1  -C 3  -alkyl, R 1  is hydrogen or alkyl or is benzyl, sulfobenzyl, phenylethyl, sulfophenylethyl, sulfophenylpropyl or C 1  -C 10  -alkyl which is unsubstituted or substituted by hydroxyl, cyano, C 1  -C 4  -alkanoyloxy or C 1  -C 8  -alkoxy, or is a radical of the formula ##STR5## R 2  is hydrogen or C 1  -C 8  -alkyl, R 3  is hydrogen or allyl, or is C 1  -C 10  -alkyl which may or may not be interrupted by oxygen and is unsubstituted or substituted by hydroxyl, cyano, C 1  -C 4  -alkanoyloxy, C 1  -C 8  -alkoxy, cyclohexyloxy, phenyl, phenoxy, sulfophenoxy, sulfophenyl or hydroxysulfonyloxy, or is cyclopentyl, or is cyclohexyl which is unsubstituted or substituted by hydroxyl, hydroxyethoxy or methyl, or is pyrrolidonylalkyl, phenyl, methoxyphenyl, sulfophenyl, C 1  -C 4  -alkoxysulfophenyl or a radical of the formula ##STR6## or R 2  and R 3 , together with the nitrogen, form a saturated 5-membered or 6-membered ring, Z is phenyl which is unsubstituted or substituted by chlorine, methyl, methoxy or acetylamino, and A is a C 2  -C 10  -alkyl radical which may or may not be interrupted by oxygen. 
     Radicals R are, in addition to hydrogen, ethyl, propyl or, preferably, methyl. In addition to those already mentioned, specific examples of radicals R 1 , R 2  and R 3  (where these fall under the general definition) are: 
     1. Unsubstituted or substituted alkyl radicals: ##STR7## 
     2. unsubstituted or substituted cycloalkyl radicals ##STR8## 
     3. Aralkyl radicals: ##STR9## and those containing C 6  H 4  CH 3  instead of C 6  H 5 . 
     4. Sulfophenyl radicals: ##STR10## 
     5. ##STR11## where n is 2, 3, 4 or 6, C 2  H 4  OCHO, C 2  H 4  OCOC 2  H 5 , C 2  H 4  OCOCH 3 , (C 2  H 4  O) 2  COCH 3 , (C 2  H 4  O) 2  CHO, (CH 2 ) 3  OCOCH 3 , C 3  H 6  OCOC 2  H 5  and (CH 2 ) 3  OCHO. 
     Examples of preferred substituents R 1  and R 3  are: ##STR12## 
     Within the scope of the general definitions, specific examples of radicals X and Y, in addition to those stated above, are methyl, ethyl, butyl, phenyl, tolylsulfonyl and the radicals of the formulae SO 2  NHCH 3 , SO 2  NHC 2  H 5 , SO 2  NHC 3  H 7 , SO 2  NHC 4  H 9 , SO 2  N(CH 3 ) 2 , SO 2  N(C 2  H 5 ) 2 , SO 2  N(C 3  H 7 ) 2  or SO 2  N(C 4  H 9 ) 2 . 
     The dyes according to the invention can be prepared by diazotizing a diazo component of an amine of the formula ##STR13## by a conventional method, and reacting the resulting diazonium salt with a coupling component of the formula H--K. 
     Of particular importance are compounds of formula Ia ##STR14## where X 1  is chlorine, bromine, methyl or trifluoromethyl, and K 1  is a radical of the formula ##STR15## where R 3  has the stated meanings. 
     Other useful compounds are those of the formula Ib ##STR16## where K 1 , X 1  and Y 3  have the meanings given in the case of formula Ia. 
     Dyes of the formula Ia which possess only one sulfo group are particularly suitable for producing level dyeings on nylon. Because of their fast rate of dyeing, they are particularly suitable for trichromatic dyeing. 
     The good lightfastness on wool, the advantageous phototropic behavior and the very good levelness are also noteworthy. 
     Some compounds according to the invention are also useful for dyeing leather. 
     In the Examples which follow, parts and percentages are by weight, unless stated otherwise. 
     PREPARATION OF THE INTERMEDIATES 
     (A) 2,4-Dichloroacetanilide 
     396 parts by volume of sulfuryl chloride are added to 270 parts of acetanilide in 1000 parts by volume of nitrobenzene in the course of 3 hours at from 50° to 70° C. (the chlorination is begun at a low temperature, which is then increased in order to suppress the precipitation of 2,4-dichloroacetanilide). When the addition of sulfuryl chloride is complete, stirring is continued for 1 hour from 70° to 75° C., after which dissolved hydrogen chloride is blown out with nitrogen. The mixture is then left to cool, whereupon 2,4-dichloroacetanilide is precipitated, and is isolated by being filtered off. 
     The product can be washed with water and dried to give 330 parts of 2,4-dichloroacetanilide, which contains about 5% of 2,4,6-trichloroacetanilide. If the nitrobenzene which is recovered as a filtrate, and in which some 2,4-dichloroacetanilide is still dissolved, is employed in a second experiment, the yield increases to 396 parts. 
     (B) 2,4-Dichloroaniline-6-sulfonic acid 
     204 parts of the crude 2,4-dichloroacetanilide are added to 300 parts of 100% strength sulfuric acid, while stirring. Thereafter, the mixture is heated further to 130° C., and 235 parts of chlorosulfonic acid are added dropwise at this temperature in such a manner that the hydrogen chloride gas liberated can readily be removed. Stirring is then continued at from 135° to 140° C. until the sulfonation is complete, this taking about 1 hour. The mixture is then left to cool to 50°-80° C., and is poured into 1300 parts by volume of water. After steam distillation for a short time, 10 parts of pure 2,4,6-trichloroaniline are obtained, as a by-product, in the distillate. The reaction mixture is then cooled to room temperature, and precipitated 2,4-dichloroaniline-6-sulfonic acid is filtered off and washed with dilute hydrochloric acid. 204 parts of 2,4-dichloroaniline-6-sulfonic acid (calculated as 100% pure) are obtained as a colorless aqueous paste, which can be used in moist form for diazotizations. H-NMR in D 2  O: 7.3 ppm, 7.6 ppm, J: 3 Hz (as the ammonium salt). 
     (C) 2,4-Dichloroaniline-5-sulfonic acid 
     204 parts of crude 2,4-dichloroacetanilide are carefully added to 600 parts of 23% strength oleum, and the mixture is heated to 140° C. and stirred at this temperature for 1 hour. It is then left to cool to 50°-80° C. and is poured into 1000 parts of water. 10 parts of 2,4,6-trichloroaniline are isolated by steam distillation, and the remaining mixture is filtered after it has cooled. The gray product isolated is stirred with about 5000 parts of water and neutralized with sodium hydroxide solution. A little active carbon is added, after which the mixture is heated to about 95° C. and filtered, and the resulting 2,4-dichloroaniline-5-sulfonic acid is precipitated from the filtrate by acidification and is isolated in a conventional manner after the mixture has cooled. The product still contains a small amount of 2,4-dichloroaniline-6-sulfonic acid, which can be removed by recrystallization from water. 2,4-Dichloroaniline-5-sulfonic acid is obtained as a colorless powder. Yield: about 140 parts. H-NMR in D 2  O: 7.45 ppm (as the ammonium salt). 
    
    
     EXAMPLE 1 
     19.5 parts of 2,4-dichloroaniline-6-sulfonic acid are dissolved in 200 parts by volume of hot water at pH 7.5-10, using sodium hydroxide solution. A wetting agent which is effective under acidic conditions and 27 parts by volume of a 23% strength aqueous sodium nitrite solution are added, and the mixture is cooled to 0°-5° C. 60 parts of ice are added, after which 55 parts of a 15-18% strength hydrochloric acid solution are introduced all at once, and the mixture is stirred for a further 3 hours at from 0° to 5° C. Thereafter, a solution or suspension of 21.2 parts of 2,6-bis-(3-hydroxypropylamino)-3-cyano-4-methylpyridine in 120 parts by volume of water and 7 parts by volume of concentrated hydrochloric acid is run in, stirring is continued for from 15 to 30 minutes, and the pH of the mixture is then slowly increased to 2-2.5 by adding sodium hydroxide solution or sodium formate. The acid formed as a result of the coupling reaction is then bound continuously by adding appropriate amounts of sodium hydroxide solution or sodium formate. When the reaction has been maintained at pH 2-2.5 for about 30-60 minutes, the pH of the mixture is increased to 3-3.5 by adding dilute sodium hydroxide solution or sodium acetate, and stirring is continued at this pH until the coupling is substantially complete. The pH of the mixture is then increased to 4.3-4.7 by adding dilute sodium hydroxide solution, after which the coupling reaction quickly ends. The resulting dye of the formula ##STR17## is precipitated virtually quantitatively by adding 80 parts of sodium chloride, and is then isolated by filtration. It is dried to give 42 parts of a reddish brown powder which still contains about 1 part of water-soluble salts in addition to 41 parts of the dye. 
     The dye dissolves in water to give a yellow solution and dyes nylon and wool in intense, lightfast, golden yellow hues. The absorption maximum of a solution of about 0.020 part of dye in 900 parts by volume of dimethylformamide and 150 parts by volume of glacial acetic acid is 427.5 nm. 
     The particular advantage of this dye is the high migrating power and the ability to dye nylon simultaneously with red and blue dyes. For example, a dye mixture of about 4 parts of this dye with about 4 parts of Acid Red 57 and 3 parts of Acid Blue 72 gives a (dark) brown. All three dyes dye nylon fabric at the same rate in the temperature range from 60° to 100° C., so that the dyeing always remains brown. The dye is also suitable for combination dyeing to achieve beige hues which are very light-fast and in particular are non-phototropic to light from incandescent lamps (no reversible change to a greener hue). 
     EXAMPLE 2 
     19.5 parts of 2,4-dichloroaniline-6-sulfonic acid are diazotized by a procedure similar to that described in Example 1. Excess nitrous acid is then destroyed in a conventional manner, and the diazonium salt mixture is buffered to pH 2-4 with sodium acetate. A solution of 16.7 parts of 1-(2-methoxyethyl)-6-hydroxy-3-cyano-4-methylpyrid-2-one in 200 parts by volume of water, 10 parts of 50% strength sodium hydroxide solution and 0.3 part of a dispersant which is effective under acidic conditions is then run in. The coupling mixture is stirred for a further 60-80 minutes, after which it is acidified to pH 0.3-0.5 with concentrated hydrochloric acid, and the precipitated dye of the formula ##STR18## is filtered off under suction, washed salt-free with a little water and dried to give 36 parts of a yellow powder. 20 parts of this powder are suspended in a mixture of 20 parts of butyldiglycol and 60 parts of 2- or 3-methoxypropanol, and the suspension is neutralized with lithium hydroxide. Clear filtration gives a honey yellow solution. This dye solution is very useful for dyeing leather lemon yellow by a conventional spray-dyeing method. The absorption maximum of the dye in a 9:1 dimethylformamide/glacial acetic acid mixture is determined as 412 nm. 
     EXAMPLE 3 
     22.1 parts of 2-trifluoromethyl-4-chloroaniline-6-sulfonic acid are diazotized by a procedure similar to that described in Example 1. 31 parts of the coupling component of the formula ##STR19## in the form of a roughly 50% strength water-moist paste, are then introduced into the diazonium salt mixture, after which the pH of the coupling mixture is brought to 4.5-5 with 25% strength sodium hydroxide solution. When coupling is complete, the mixture is neutralized with further sodium hydroxide solution and is then spray dried. 
     73 parts of a red powder are obtained. The resulting dye is of the formula ##STR20## and has an absorption maximum of 430 nm in a 9:1 dimethylformamide/glacial acetic acid mixture. It dyes wool and nylon in fast intense golden yellow hues. 
     EXAMPLE 4 
     19.5 parts of 2,4-dichloroaniline-6-sulfonic acid are diazotized by a procedure similar to that described in Example 1. When excess nitrous acid has been destroyed, 24.2 parts of 2-phenyl-4,6-bis-(3-hydroxypropylamino)-pyrimidine are added, and stirring is continued until the coupling component has dissolved. Thereafter, a dispersant which is highly effective at pH 7-10 is added and the pH of the coupling mixture is brought to 8.5-9.2 with sodium hydroxide solution and then with a little sodium carbonate solution (as a buffer). Stirring is continued overnight, and the resulting dye of the formula ##STR21## (λmax: 431.5 nm (CH 3 ) 2  NCHO/CH 3  CO 2  H=9:1) is then precipitated by adding about 30 parts of sodium chloride and acidifying the mixture to pH 4-4.5, and is isolated in a conventional manner to give about 50 parts of a reddish brown powder which dissolves in water to give a yellow solution and dyes nylon fabric and wool in very fast golden yellow hues. The dye has great migrating power. 
     
                                           TABLE 1                                 
__________________________________________________________________________
 ##STR22##                                                                
                                      λmax                         
No.                                                                       
   R  R.sup.1   R.sup.2    R.sup.3                                        
                              Hue     (nm)                                
__________________________________________________________________________
 1 Cl H         C.sub.3 H.sub.6 OCH.sub.3                                 
                           C.sub.3 H.sub.7                                
                              yellow  413                                 
 2 Cl H         C.sub.3 H.sub.6 OH                                        
                           C.sub.3 H.sub.7                                
                              yellow  413                                 
 3 Cl H         C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH                       
                           CH.sub.3                                       
                              yellow  411                                 
 4 Cl H         C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH                       
                           H  yellow  412                                 
 5 Cl H         C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH                       
                           CH.sub.3                                       
                              yellow  409                                 
 6 Cl H         C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OCH.sub.3                
                           CH.sub.3                                       
                              yellow  409                                 
 7 Cl H         C.sub.2 H.sub.4 OC.sub.4 H.sub.9 (n)                      
                           CH.sub.3                                       
                              yellow  409                                 
 8 Cl H         C.sub.3 H.sub.6 OCH.sub.3                                 
                           CH.sub.3                                       
                              yellow  410                                 
 9 Cl H         C.sub.3 H.sub.6 OC.sub.2 H.sub.5                          
                           CH.sub.3                                       
                              yellow  410                                 
10 Cl C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH                                 
                H          CH.sub.3                                       
                              yellow  412                                 
11 Cl C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OC.sub.2 H.sub.5                   
                H          CH.sub.3                                       
                              yellow  411                                 
12 Cl C.sub.2 H.sub.5                                                     
                C.sub.2 H.sub.4 OH                                        
                           CH.sub.3                                       
                              golden yellow                               
                                      422                                 
13 Cl CH.sub.3  C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH                       
                           CH.sub.3                                       
                              golden yellow                               
                                      420                                 
14 Cl C.sub.2 H.sub.5                                                     
                C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH                       
                           CH.sub.3                                       
                              golden yellow                               
                                      422                                 
15 Cl C.sub.2 H.sub.5                                                     
                C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH                       
                           CH.sub.3                                       
                              golden yellow                               
                                      421                                 
16 Cl CH.sub.2 CHCH.sub.2                                                 
                C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH                       
                           CH.sub.3                                       
                              golden yellow                               
                                      422                                 
17 Cl CH(CH.sub.3).sub.2                                                  
                C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH                       
                           CH.sub.3                                       
                              golden yellow                               
                                      420                                 
18 Cl CH.sub.2 CH.sub.2 OCH.sub.3                                         
                CH.sub.2 CH.sub.2 OCH.sub.3                               
                           CH.sub. 3                                      
                              golden yellow                               
                                      419                                 
19 Cl (CH.sub.2).sub.3 OCH.sub.3                                          
                CH.sub.2 CH.sub.2 OCH.sub.3                               
                           CH.sub.3                                       
                              golden yellow                               
                                      421                                 
20 Cl (CH.sub.2).sub.3 OCH.sub.3                                          
                (CH.sub.2).sub.3 OCH.sub.3                                
                           CH.sub.3                                       
                              golden yellow                               
                                      427                                 
21 Cl                                                                     
       ##STR23##                                                          
                C.sub.2 H.sub.4 OCH.sub.3                                 
                           CH.sub.3                                       
                              golden yellow                               
                                      422                                 
22 Cl CH.sub.2 CH.sub.2 OCH.sub.3                                         
                (CH.sub.2).sub.3 OCH.sub.3                                
                           CH.sub.3                                       
                              golden yellow                               
                                      423                                 
23 Cl CH.sub.2 CH.sub.2 OCH.sub.3                                         
                CH.sub.2 CH.sub.2 OH                                      
                           CH.sub.3                                       
                              golden yellow                               
                                      423                                 
24 Cl CH.sub.2 CH.sub.2 OCH.sub.3                                         
                 ##STR24## CH.sub.3                                       
                              golden yellow                               
                                      423                                 
25 Cl CH.sub.2 CH.sub.2 OCH.sub.3                                         
                CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                        
                           CH.sub.3                                       
                              golden yellow                               
                                      421                                 
26 Cl CH.sub.2 CH.sub.2 OCH.sub.3                                         
                (CH.sub.2).sub.3 OCH(CH.sub.3).sub.2                      
                           CH.sub.3                                       
                              golden yellow                               
                                      423                                 
27 Cl CH.sub.2 CH.sub.2 OCH.sub.3                                         
                (CH.sub.2).sub.3 O(CH.sub.2).sub.4 OH                     
                           CH.sub.3                                       
                              golden yellow                               
                                      423                                 
28 Cl CH.sub.2 CH.sub.2 OCH.sub. 3                                        
                (CH.sub.2).sub.3 OH                                       
                           CH.sub.3                                       
                              golden yellow                               
                                      424                                 
29 Cl                                                                     
       ##STR25##                                                          
                CH.sub.2 CH.sub.2 OCH.sub.3                               
                           CH.sub.3                                       
                              golden yellow                               
                                      423                                 
30 Cl                                                                     
       ##STR26##                                                          
                (CH.sub.2).sub.3 OCH.sub.3                                
                           CH.sub.3                                       
                              orange  423                                 
31 Cl                                                                     
       ##STR27##                                                          
                (CH.sub.2).sub.2 OH                                       
                           CH.sub.3                                       
                              golden yellow                               
                                      422                                 
32 Cl                                                                     
       ##STR28##                                                          
                (CH.sub.2).sub.3 OH                                       
                           CH.sub.3                                       
                              orange  424                                 
33 Cl                                                                     
       ##STR29##                                                          
                (CH.sub.2).sub.3 OC.sub.2 H.sub.5                         
                           CH.sub.3                                       
                              orange  424                                 
34 Cl                                                                     
       ##STR30##                                                          
                 ##STR31## CH.sub.3                                       
                              orange  424                                 
35 Cl (CH.sub.2).sub.3 OH                                                 
                (CH.sub.2).sub.2 OH                                       
                           CH.sub.3                                       
                              golden yellow                               
                                      425                                 
36 Cl (CH.sub.2).sub.3 OH                                                 
                 ##STR32## CH.sub.3                                       
                              golden yellow                               
                                      426                                 
37 Cl (CH.sub.2).sub.3 OH                                                 
                (CH.sub.2).sub.2 OCH.sub.3                                
                           CH.sub.3                                       
                              golden yellow                               
                                      426                                 
38 Cl (CH.sub.2).sub.3 OH                                                 
                (CH.sub.2).sub.3 OCH.sub.3                                
                           CH.sub.3                                       
                              golden yellow                               
                                      427                                 
39 Cl (CH.sub.2).sub.3 OH                                                 
                (CH.sub.2).sub.3 OC.sub.2 H.sub.5                         
                           CH.sub.3                                       
                              golden yellow                               
                                      426                                 
40 Cl (CH.sub.2).sub.2 OH                                                 
                (CH.sub.2).sub.2 OH                                       
                           CH.sub.3                                       
                              golden yellow                               
                                      420                                 
41 Cl (CH.sub.2).sub.2 OH                                                 
                (CH.sub.2).sub.3 OH                                       
                           CH.sub.3                                       
                              golden yellow                               
                                      423                                 
42 Cl (CH.sub.2).sub.2 OH                                                 
                 ##STR33## CH.sub.3                                       
                              golden yellow                               
                                      423                                 
43 Cl (CH.sub.2).sub.2 OH                                                 
                (CH.sub.2).sub.2 OCH.sub.3                                
                           CH.sub.3                                       
                              golden yellow                               
                                      421                                 
44 Cl (CH.sub.2).sub.2 OH                                                 
                (CH.sub.2).sub.3 OCH.sub.3                                
                           CH.sub.3                                       
                              golden yellow                               
                                      423                                 
45 Cl (CH.sub.2).sub.2 OH                                                 
                (CH.sub.2).sub.3 OC.sub.2 H.sub.5                         
                           CH.sub.3                                       
                              golden yellow                               
                                      423                                 
46 Cl (CH.sub.2).sub.2 OH                                                 
                C.sub.4 H.sub.9 (n)                                       
                           CH.sub.3                                       
                              golden yellow                               
                                      427                                 
47 Cl (CH.sub.2).sub.2 OH                                                 
                (CH.sub.2).sub.3 OCH.sub.2 C.sub.6 H.sub.5                
                           CH.sub.3                                       
                              golden yellow                               
                                      425                                 
48 Cl (CH.sub.2).sub.2 OH                                                 
                (CH.sub.2).sub.2 C.sub.6 H.sub.5                          
                           CH.sub.3                                       
                              golden yellow                               
                                      422                                 
49 Cl (CH.sub.2).sub.2 OH                                                 
                 ##STR34## CH.sub.3                                       
                              golden yellow                               
                                      422                                 
50 Cl (CH.sub.2).sub.2 OH                                                 
                 ##STR35## CH.sub.3                                       
                              golden yellow                               
                                      423                                 
51 Cl C.sub.2 H.sub.5                                                     
                 ##STR36## CH.sub.3                                       
                              golden yellow                               
                                      422                                 
52 Cl C.sub.2 H.sub.5                                                     
                C.sub.2 H.sub.5                                           
                           CH.sub.3                                       
                              golden yellow                               
                                      420                                 
53 Cl (CH.sub.2).sub.2 CN                                                 
                (CH.sub.2).sub.3 OH                                       
                           CH.sub.3                                       
                              golden yellow                               
                                      422                                 
54 Cl (CH.sub.2).sub.5 CN                                                 
                (CH.sub.2).sub.3 OH                                       
                           CH.sub.3                                       
                              golden yellow                               
                                      423                                 
55 Cl (CH.sub.2).sub.2 C.sub.6 H.sub.5                                    
                (CH.sub.2).sub.2 OH                                       
                           CH.sub.3                                       
                              golden yellow                               
                                      421                                 
56 Cl                                                                     
       ##STR37##                                                          
                C.sub.4 H.sub.9 (n)                                       
                           CH.sub.3                                       
                              golden yellow                               
                                      423                                 
57 Cl CH.sub.2 CHCH.sub.2                                                 
                (CH.sub.2).sub.2 OH                                       
                           CH.sub.3                                       
                              golden yellow                               
                                      422                                 
58 Cl CH.sub.2 CHCH.sub.2                                                 
                (CH.sub.2).sub.3 OH                                       
                           CH.sub.3                                       
                              golden yellow                               
                                      423                                 
59 Br (CH.sub.2).sub.3 OH                                                 
                (CH.sub.2).sub.3 OH                                       
                           CH.sub.3                                       
                              golden yellow                               
                                      429                                 
60 CF.sub.3                                                               
      (CH.sub.2).sub.3 OH                                                 
                (CH.sub.2).sub.3 OH                                       
                           CH.sub.3                                       
                              golden yellow                               
                                      430                                 
61 CF.sub.3                                                               
      (CH.sub.2).sub.2 OCH.sub.3                                          
                (CH.sub.2).sub.2 OH                                       
                           CH.sub.3                                       
                              golden yellow                               
                                      428                                 
62 Cl                                                                     
       ##STR38##                                                          
                (CH.sub.2).sub.2 OH                                       
                           CH.sub.3                                       
                              golden yellow                               
                                      425                                 
63 Cl                                                                     
       ##STR39##                                                          
                (CH.sub.2).sub.3 OH                                       
                           CH.sub.3                                       
                              golden yellow                               
                                      426                                 
64 Cl                                                                     
       ##STR40##                                                          
                (CH.sub.2).sub.3 OH                                       
                           CH.sub.3                                       
                              golden yellow                               
                                      426                                 
65 Cl                                                                     
       ##STR41##                                                          
                (CH.sub.2).sub.2 OH                                       
                           CH.sub.3                                       
                              golden yellow                               
                                      424                                 
66 Cl (CH.sub.2 ).sub.2 OCOCH.sub.3                                       
                (CH.sub.2).sub.2 OCOCH.sub.3                              
                           CH.sub.3                                       
                              golden yellow                               
                                      420                                 
67 Cl (CH.sub.2).sub.3 OCHO                                               
                (CH.sub.2).sub.3 OCHO                                     
                           CH.sub.3                                       
                              golden yellow                               
                                      421                                 
68 Cl (CH.sub.2).sub.2 OCH.sub.3                                          
                (CH.sub.2).sub.3 OCHO                                     
                           CH.sub.3                                       
                              golden yellow                               
                                      421                                 
69 Cl (CH.sub.2).sub.3 OCHO                                               
                (CH.sub.2).sub.2 OCH.sub.3                                
                           CH.sub.3                                       
                              golden yellow                               
                                      421                                 
70 Cl (CH.sub.2).sub.4 OH                                                 
                (CH.sub.2).sub.4 OH                                       
                           CH.sub.3                                       
                              golden yellow                               
                                      430                                 
71 Cl (CH.sub.2).sub.4 OH                                                 
                (CH.sub.2).sub.3 OH                                       
                           CH.sub.3                                       
                              golden yellow                               
                                      429                                 
72 Cl (CH.sub.2).sub.4 OH                                                 
                (CH.sub.2).sub.2 OH                                       
                           CH.sub.3                                       
                              golden yellow                               
                                      429                                 
73 Cl (CH.sub.2).sub.4 OH                                                 
                (CH.sub.2).sub.2 OCH.sub.3                                
                           CH.sub.3                                       
                              golden yellow                               
                                      428                                 
__________________________________________________________________________
 
    
     
                                           TABLE 2                                 
__________________________________________________________________________
 ##STR42##                                                                
No.                                                                       
   R.sup.1        R.sup.2  R.sup.3                                        
                                Hue                                       
__________________________________________________________________________
    ##STR43##     C.sub.2 H.sub.5                                         
                           H    golden yellow                             
2                                                                         
    ##STR44##     C.sub.2 H.sub.5                                         
                           C.sub.2 H.sub.5                                
                                orange                                    
3                                                                         
    ##STR45##     C.sub.4 H.sub.9 (n)                                     
                           H    golden yellow                             
4                                                                         
    ##STR46##     C.sub.3 H.sub.6 OCH.sub.3                               
                           H    golden yellow                             
5                                                                         
    ##STR47##     C.sub.2 H.sub.4 OCH.sub.3                               
                           H    golden yellow                             
6                                                                         
    ##STR48##     C.sub.3 H.sub.6 OC.sub.2 H.sub.5                        
                           H    golden yellow                             
7                                                                         
    ##STR49##     C.sub.3 H.sub.6 OH                                      
                           H    golden yellow                             
8                                                                         
    ##STR50##     C.sub.4 H.sub.8 OH                                      
                           H    golden yellow                             
9                                                                         
    ##STR51##     C.sub.4 H.sub.9 (n)                                     
                           C.sub.4 H.sub.9 (n)                            
                                orange                                    
10                                                                        
    ##STR52##                                                             
                   ##STR53##                                              
                           H    golden yellow                             
11                                                                        
    ##STR54##     C.sub.2 H.sub.4 OH                                      
                           H    golden yellow                             
12                                                                        
    ##STR55##     C.sub.3 H.sub.6 OH                                      
                           H    golden yellow                             
13                                                                        
    ##STR56##     C.sub.4 H.sub.9 (n)                                     
                           H    golden yellow                             
14                                                                        
    ##STR57##     C.sub.3 H.sub.6 OCH.sub.3                               
                           H    golden yellow                             
15                                                                        
    ##STR58##     C.sub.2 H.sub.4 OCH.sub.3                               
                           H    golden yellow                             
16                                                                        
    ##STR59##                                                             
                   ##STR60##                                              
                           H    golden yellow                             
17 C.sub.4 H.sub.8 OH                                                     
                   ##STR61##                                              
                           H    golden yellow                             
18 C.sub.3 H.sub.6 OH                                                     
                   ##STR62##    orange                                    
19 C.sub.2 H.sub.4 OCH.sub.3                                              
                   ##STR63##    orange                                    
20 C.sub.3 H.sub.6 OCH.sub.3                                              
                   ##STR64##    orange                                    
21 C.sub.3 H.sub.6 OH                                                     
                   ##STR65##    orange                                    
__________________________________________________________________________
 
    
     
                                           TABLE 3                                 
__________________________________________________________________________
 ##STR66##                                                                
                                               λmax                
No.                                                                       
   R  R.sup.1      R.sup.2   R.sup.3   Hue     (nm)                       
__________________________________________________________________________
1  Cl C.sub.3 H.sub.6 OH                                                  
                   C.sub.6 H.sub.5                                        
                             C.sub.2 H.sub.4 OH                           
                                       golden yellow                      
                                               429                        
2  Cl C.sub.3 H.sub.6 OH                                                  
                   C.sub.6 H.sub.5                                        
                             C.sub.2 H.sub.4 OCH.sub.3                    
                                       golden yellow                      
                                               428                        
3  Cl C.sub.3 H.sub.6 OH                                                  
                   C.sub.6 H.sub.5                                        
                             C.sub.3 H.sub.6 OCH.sub.3                    
                                       golden yellow                      
                                               430                        
4  Cl C.sub.3 H.sub.6 OH                                                  
                   C.sub.6 H.sub.5                                        
                             C.sub.2 H.sub.4 OC.sub.2 H.sub.5             
                                       golden yellow                      
                                               428                        
5  Cl C.sub.3 H.sub.6 OH                                                  
                   C.sub.6 H.sub.5                                        
                             C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH          
                                       yellow  427                        
6  Cl C.sub.3 H.sub.6 OH                                                  
                   C.sub.6 H.sub.5                                        
                             C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OCH.sub.3   
                                       yellow  427                        
7  Cl C.sub.3 H.sub.6 OH                                                  
                   C.sub.6 H.sub.5                                        
                             C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OH          
                                       golden yellow                      
                                               430                        
8  Cl C.sub.3 H.sub.6 OH                                                  
                   C.sub.6 H.sub.5                                        
                             C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH          
                                       golden yellow                      
                                               430                        
9  Cl C.sub.2 H.sub.4 OH                                                  
                   C.sub.6 H.sub.5                                        
                             C.sub.2 H.sub.4 OCH.sub.3                    
                                       yellow  426                        
10 Cl C.sub.2 H.sub.4 OH                                                  
                   C.sub.6 H.sub.5                                        
                             C.sub.3 H.sub.6 OCH.sub.3                    
                                       yellow  427                        
11 Cl C.sub.2 H.sub.4 OH                                                  
                   C.sub.6 H.sub.5                                        
                             C.sub.3 H.sub.6 OC.sub.3 H.sub.7             
                                       yellow  428                        
12 Cl C.sub.2 H.sub.4 OCH.sub.3                                           
                   C.sub.6 H.sub.5                                        
                             C.sub.2 H.sub.4 OCH.sub.3                    
                                       yellow  426                        
13 Cl C.sub.2 H.sub.4 OCH.sub.3                                           
                   C.sub.6 H.sub.5                                        
                             C.sub.3 H.sub.6 OCH.sub.3                    
                                       yellow  428                        
14 Cl C.sub.3 H.sub.6 OCH.sub.3                                           
                   C.sub.6 H.sub.5                                        
                             C.sub.3 H.sub.6 OCH.sub.3                    
                                       golden yellow                      
                                               429                        
15 Cl                                                                     
       ##STR67##   C.sub.6 H.sub.5                                        
                             C.sub.3 H.sub.6 OCH.sub.3                    
                                       golden yellow                      
                                               430                        
16 Cl                                                                     
       ##STR68##   C.sub.6 H.sub.5                                        
                              ##STR69##                                   
                                       golden yellow                      
                                               431                        
17 Br                                                                     
       ##STR70##   C.sub.6 H.sub.5                                        
                              ##STR71##                                   
                                       golden yellow                      
                                               431                        
18 Br C.sub.3 H.sub.6 OH                                                  
                   C.sub.3 H.sub.6                                        
                             C.sub.3 H.sub.6 OH                           
                                       golden yellow                      
                                               432                        
19 Cl C.sub.3 H.sub.6 OH                                                  
                    ##STR72##                                             
                             C.sub.3 H.sub.6 OH                           
                                       golden yellow                      
                                               432                        
20 Cl C.sub.3 H.sub.6 OH                                                  
                    ##STR73##                                             
                             C.sub.3 H.sub.6 OH                           
                                       golden yellow                      
                                               432                        
21 Cl C.sub.4 H.sub.8 OH                                                  
                   C.sub.6 H.sub.5                                        
                             C.sub.4 H.sub.8 OH                           
                                       golden yellow                      
                                               433                        
22 Cl C.sub.2 H.sub.4 OH                                                  
                    ##STR74##                                             
                             C.sub.2 H.sub.4 OH                           
                                       golden yellow                      
                                               431                        
23 Cl                                                                     
       ##STR75##                                                          
                    ##STR76##                                             
                             C.sub.2 H.sub.4 OH                           
                                       yellow  428                        
24 CF.sub.3                                                               
      C.sub.3 H.sub.6 OH                                                  
                   C.sub.6 H.sub.6                                        
                             C.sub.3 H.sub.6 OH                           
                                       golden yellow                      
                                               434                        
25 CF.sub.3                                                               
      C.sub.3 H.sub.6 OH                                                  
                   C.sub.6 H.sub.5                                        
                             C.sub.2 H.sub.4 OH                           
                                       golden yellow                      
                                               433                        
26 CF.sub.3                                                               
       ##STR77##   C.sub.6 H.sub.5                                        
                             C.sub.2 H.sub.4 OH                           
                                       golden yellow                      
                                               433                        
27 CF.sub.3                                                               
       ##STR78##   C.sub.6 H.sub.5                                        
                              ##STR79##                                   
                                       golden yellow                      
                                               435                        
28 CF.sub.3                                                               
      C.sub.2 H.sub.4 OCH.sub.3                                           
                   C.sub.6 H.sub.5                                        
                              ##STR80##                                   
                                       golden yellow                      
                                               432                        
29 CF.sub.3                                                               
      C.sub.2 H.sub.4 OCH.sub.3                                           
                   C.sub.6 H.sub.5                                        
                             C.sub.2 H.sub.4 OH                           
                                       golden yellow                      
                                               432                        
30 CF.sub.3                                                               
      C.sub.2 H.sub.4 OCH.sub.3                                           
                   C.sub.6 H.sub.5                                        
                             C.sub.3 H.sub.6 OH                           
                                       golden yellow                      
                                               432                        
31 CF.sub.3                                                               
      C.sub. 3 H.sub.6 OCH.sub.3                                          
                   C.sub.6 H.sub.5                                        
                             C.sub.3 H.sub.6 OH                           
                                       golden yellow                      
                                               435                        
32 CF.sub.3                                                               
       ##STR81##                                                          
                    ##STR82##                                             
                             C.sub.2 H.sub.4 OH                           
                                       golden yellow                      
                                               433                        
33 Cl                                                                     
       ##STR83##   C.sub.6 H.sub.5                                        
                              ##STR84##                                   
                                       golden yellow                      
                                               434                        
34 CH.sub.3                                                               
      C.sub.2 H.sub.4 OH                                                  
                   C.sub.6 H.sub.5                                        
                             C.sub.2 H.sub.4 OH                           
                                       golden yellow                      
                                               432                        
__________________________________________________________________________
 
    
     
                       TABLE 4                                                     
______________________________________                                    
 ##STR85##                                                                
                                         λmax                      
No. R  R.sup.1  R.sup.2       R.sup.3                                     
                                   Hue   (nm)                             
______________________________________                                    
 1Cl   Cl       C.sub.2 H.sub.4 OH                                        
                              H    green-                                 
                                         412                              
                                   ish                                    
                                   yellow                                 
 2Cl   Cl       C.sub.2 H.sub.4 OH                                        
                              CH.sub.3                                    
                                   green-                                 
                                         412                              
                                   ish                                    
                                   yellow                                 
 3Cl   Cl       C.sub.2 H.sub.4 OH                                        
                              C.sub.2 H.sub.5                             
                                   green-                                 
                                         411                              
                                   ish                                    
                                   yellow                                 
 4Cl   Cl       C.sub.2 H.sub.4 OH                                        
                              C.sub.3 H.sub.7                             
                                   green-                                 
                                         410                              
                              (n)  ish                                    
                                   yellow                                 
 5Cl   Cl       C.sub.3 H.sub.6 OH                                        
                              CH.sub.3                                    
                                   green-                                 
                                         412                              
                                   ish                                    
                                   yellow                                 
 6Cl   Cl       C.sub.3 H.sub.6 OH                                        
                              CH.sub.3                                    
                                   green-                                 
                                         412                              
                                   ish                                    
                                   yellow                                 
 7Cl   Cl       C.sub.3 H.sub.6 OH                                        
                              C.sub.3 H.sub.7                             
                                   green-                                 
                                         411                              
                              (n)  ish                                    
                                   yellow                                 
 8Cl   Cl       C.sub.3 H.sub.6 OCOCH.sub.3                               
                              CH.sub.3                                    
                                   green-                                 
                                         413                              
                                   ish                                    
                                   yellow                                 
 9Cl   Cl       C.sub.3 H.sub.6 OCH.sub.3                                 
                              C.sub.3 H.sub.7                             
                                   green-                                 
                                         412                              
                              (n)  ish                                    
                                   yellow                                 
10Cl   Cl       C.sub.3 H.sub.6 OCH.sub.3                                 
                              CH.sub.3                                    
                                   green-                                 
                                         412                              
                                   ish                                    
                                   yellow                                 
11Br   Cl       C.sub.3 H.sub.6 OCH.sub.3                                 
                              CH.sub.3                                    
                                   green-                                 
                                         413                              
                                   ish                                    
                                   yellow                                 
12Cl   Cl       C.sub.3 H.sub.6 OCH.sub.3                                 
                              H    green-                                 
                                         412                              
                                   ish                                    
                                   yellow                                 
13Cl   Cl       C.sub.6 H.sub.13 (n)                                      
                              CH.sub.3                                    
                                   green-                                 
                                         413                              
                                   ish                                    
                                   yellow                                 
14Cl   Cl       C.sub.3 H.sub.6 OC.sub.2 H.sub.5                          
                              CH.sub.3                                    
                                   green-                                 
                                         413                              
                                   ish                                    
                                   yellow                                 
15Cl   Cl       C.sub.3 H.sub.6 OC.sub.3 H.sub.7                          
                              CH.sub.3                                    
                                   green-                                 
                                         412                              
                                   ish                                    
                                   yellow                                 
16Cl   Cl       C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH                       
                              CH.sub.3                                    
                                   green-                                 
                                         412                              
                                   ish                                    
                                   yellow                                 
17Cl   CF.sub.3 C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH                       
                              CH.sub.3                                    
                                   green-                                 
                                         407                              
                                   ish                                    
                                   yellow                                 
18Cl   CF.sub.3 C.sub.6 H.sub.12 OH                                       
                              CH.sub.3                                    
                                   green-                                 
                                         408                              
                                   ish                                    
                                   yellow                                 
19Cl   Cl       C.sub.6 H.sub.12 OH                                       
                              CH.sub.3                                    
                                   green-                                 
                                         413                              
                                   ish                                    
                                   yellow                                 
20Cl   CF.sub.3 C.sub.3 H.sub.6 OCH.sub.3                                 
                              CH.sub.3                                    
                                   green-                                 
                                         407                              
                                   ish                                    
                                   yellow                                 
21Cl   CF.sub.3 CH.sub.2 CH.sub.2C.sub.6 H.sub.5                          
                              CH.sub.3                                    
                                   green-                                 
                                         407                              
                                   ish                                    
                                   yellow                                 
22Cl   CF.sub.3 CH.sub.2 CHCH.sub.2                                       
                              CH.sub.3                                    
                                   green-                                 
                                         407                              
                                   ish                                    
                                   yellow                                 
23Cl   CF.sub.3 C.sub.6 H.sub.13 (n)                                      
                              CH.sub.3                                    
                                   green-                                 
                                         408                              
                                   ish                                    
                                   yellow                                 
24Cl   CF.sub.3                                                           
                 ##STR86##    CH.sub.3                                    
                                   green- ish yellow                      
                                         407                              
25Cl   Cl                                                                 
                 ##STR87##    CH.sub.3                                    
                                   green- ish yellow                      
                                         412                              
26Cl   Cl                                                                 
                 ##STR88##    CH.sub.3                                    
                                   green- ish yellow                      
                                         413                              
27Cl   Cl       C.sub.4 H.sub.8 OH                                        
                              CH.sub.3                                    
                                   green-                                 
                                         413                              
                                   ish                                    
                                   yellow                                 
28Cl   Cl       C.sub.6 H.sub.12 OH                                       
                              CH.sub.3                                    
                                   green-                                 
                                         413                              
                                   ish                                    
                                   yellow                                 
29H    SO.sub.2 C.sub.6 H.sub.5                                           
                C.sub.4 H.sub.8 OH                                        
                              CH.sub.3                                    
                                   green-                                 
                                   ish                                    
                                   yellow                                 
30H    SO.sub.2 C.sub.6 H.sub.5                                           
                C.sub.3 H.sub.6 OH                                        
                              CH.sub.3                                    
                                   green-                                 
                                   ish                                    
                                   yellow                                 
31Cl   CH.sub.3 C.sub.3 H.sub.6 OH                                        
                              CH.sub.3                                    
                                   green-                                 
                                         411                              
                                   ish                                    
                                   yellow                                 
32Cl   CH.sub.3 C.sub.2 H.sub.4 OH                                        
                              CH.sub.3                                    
                                   green-                                 
                                         412                              
                                   ish                                    
                                   yellow                                 
33Cl   CH.sub.3 C.sub.3 H.sub.6 OCH.sub.3                                 
                              CH.sub.3                                    
                                   green-                                 
                                         411                              
                                   ish                                    
                                   yellow                                 
34Cl   Br       C.sub.3 H.sub.6 OCH.sub.3                                 
                              CH.sub.3                                    
                                   green-                                 
                                         413                              
                                   ish                                    
                                   yellow                                 
35Cl   Br       C.sub.3 H.sub.6 OH                                        
                              CH.sub.3                                    
                                   green-                                 
                                         413                              
                                   ish                                    
                                   yellow                                 
36Cl   Br       C.sub.4 H.sub.8 OH                                        
                              CH.sub.3                                    
                                   green-                                 
                                         413                              
                                   ish                                    
                                   yellow                                 
37CH.sub.3                                                                
       Br       C.sub.4 H.sub.8 OH                                        
                              CH.sub.3                                    
                                   green-                                 
                                         414                              
                                   ish                                    
                                   yellow                                 
38CH.sub.3                                                                
       Br       C.sub.3 H.sub.6 OH                                        
                              CH.sub.3                                    
                                   green-                                 
                                         414                              
                                   ish                                    
                                   yellow                                 
39CH.sub.3                                                                
       Br       C.sub.3 H.sub.6 OCH.sub. 3                                
                              CH.sub.3                                    
                                   green-                                 
                                         414                              
                                   ish                                    
                                   yellow                                 
40CH.sub.3                                                                
       Br       C.sub.2 H.sub.4 OCH.sub.3                                 
                              CH.sub.3                                    
                                   green-                                 
                                         414                              
                                   ish                                    
                                   yellow                                 
______________________________________                                    
 
    
     
                       TABLE 5                                                     
______________________________________                                    
 ##STR89##                                                                
                                       λmax                        
No.  R      A                  Hue     (nm)                               
______________________________________                                    
1    Cl     C.sub.2 H.sub.4    greenish                                   
                                       413                                
                               yellow                                     
2    Cl     C.sub.3 H.sub.6    greenish                                   
                                       413                                
                               yellow                                     
3    Cl                                                                   
             ##STR90##         greenish yellow                            
                                       413                                
4    Cl     (CH.sub.2).sub.6   greenish                                   
                                       412                                
                               yellow                                     
5    Cl     (CH.sub.2).sub.3 O(CH.sub.2).sub.3                            
                               greenish                                   
                                       413                                
                               yellow                                     
6    Br     (CH.sub.2).sub.3 O(CH.sub.2).sub.2 O(CH.sub.2).sub.3          
                               greenish                                   
                                       413                                
                               yellow                                     
7    Br     C.sub.3 H.sub.6    greenish                                   
                                       413                                
                               yellow                                     
8    CF.sub.3                                                             
            C.sub.2 H.sub.4    greenish                                   
                                       417                                
                               yellow                                     
9    CF.sub.3                                                             
            C.sub.3 H.sub.6    greenish                                   
                                       408                                
                               yellow                                     
10   CF.sub.3                                                             
             ##STR91##         greenish yellow                            
                                       408                                
11   CF.sub.3                                                             
            (CH.sub.2).sub.6   greenish                                   
                                       408                                
                               yellow                                     
12   CF.sub.3                                                             
            (CH.sub.2).sub.3 O(CH.sub.2).sub.3                            
                               greenish                                   
                                       408                                
                               yellow                                     
13   Cl     (CH.sub.2).sub.3 O(CH.sub.2).sub.2 O(CH.sub.2).sub.3          
                               greenish                                   
                                       412                                
                               yellow                                     
14   Cl     (CH.sub.2).sub.3 O(CH.sub.2).sub.4 O(CH.sub.2).sub.3          
                               greenish                                   
                                       413                                
                               yellow                                     
15   Cl     CH.sub.2(CH.sub.3).sub.2CH.sub.2                              
                               greenish                                   
                                       413                                
                               yellow                                     
______________________________________                                    
 
    
     
                       TABLE 6                                                     
______________________________________                                    
 ##STR92##                                                                
No.  A                R.sup.1                                             
                             R.sup.2   Hue                                
______________________________________                                    
 1   CH.sub.2 CH.sub.2                                                    
                      Cl     C.sub.2 H.sub.4 OH                           
                                       golden                             
                                       yellow                             
 2   (CH.sub.2).sub.3 Cl     C.sub.2 H.sub.4 OH                           
                                       golden                             
                                       yellow                             
 3   (CH.sub.2).sub.3 Cl     C.sub.3 H.sub.6 OH                           
                                       golden                             
                                       yellow                             
 4   (CH.sub.2).sub.3 Cl     C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH          
                                       golden                             
                                       yellow                             
 5   (CH.sub.2).sub.3 Cl     C.sub.2 H.sub.4 OCH.sub.3                    
                                       golden                             
                                       yellow                             
 6   (CH.sub.2).sub.3 Cl     C.sub.3 H.sub.6 OCH.sub.3                    
                                       golden                             
                                       yellow                             
 7   (CH.sub.2).sub.4 Cl     C.sub.2 H.sub.4 OH                           
                                       golden                             
                                       yellow                             
 8   (CH.sub.2).sub.4 Cl     C.sub.3 H.sub.6 OH                           
                                       golden                             
                                       yellow                             
 9   (CH.sub.2).sub.3 O(CH.sub.2).sub.2 O(CH.sub.2).sub.3                 
                      Cl     C.sub.2 H.sub.4 OH                           
                                       golden                             
                                       yellow                             
10   (CH.sub.2).sub.3 O(CH.sub.2).sub.2 O(CH.sub.2).sub.3                 
                      Cl     C.sub.3 H.sub.6 OH                           
                                       golden                             
                                       yellow                             
11   (CH.sub.2).sub.3 O(CH.sub.2).sub.4 O(CH.sub.2).sub.3                 
                      Cl     C.sub.3 H.sub.6 OH                           
                                       golden                             
                                       yellow                             
12   (CH.sub.2).sub.3 O(CH.sub.2).sub.4 O(CH.sub.2).sub.3                 
                      Cl     C.sub.2 H.sub.4 OCH.sub.3                    
                                       golden                             
                                       yellow                             
13   (CH.sub.2).sub. 3 O(CH.sub.2).sub.4 O(CH.sub.2).sub.3                
                      Cl     C.sub.3 H.sub.6 OCH.sub.3                    
                                       golden                             
                                       yellow                             
14   (CH.sub.2).sub.3 O(CH.sub.2).sub.4 O(CH.sub.2).sub.3                 
                      CF.sub.3                                            
                             C.sub.3 H.sub.6 OCH.sub.3                    
                                       golden                             
                                       yellow                             
15   (CH.sub.2).sub.3 CF.sub.3                                            
                             C.sub.3 H.sub.6 OCH.sub.3                    
                                       golden                             
                                       yellow                             
16   (CH.sub.2).sub.6 Cl     C.sub.2 H.sub.4 OCH.sub.3                    
                                       golden                             
                                       yellow                             
17                                                                        
      ##STR93##       Cl     C.sub.2 H.sub.4 OH                           
                                       golden  yellow                     
18                                                                        
      ##STR94##       Cl     C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH          
                                       golden  yellow                     
19   (CH.sub.2).sub.3 Cl     C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH          
                                       golden                             
                                       yellow                             
20   (CH.sub.2).sub.3 Cl     C.sub.4 H.sub.8 OH                           
                                       golden                             
                                       yellow                             
21   (CH.sub.2).sub.3 CH.sub.3                                            
                             C.sub.2 H.sub. 4 OH                          
                                       golden                             
                                       yellow                             
______________________________________                                    
 
    
     
                                           TABLE 7                                 
__________________________________________________________________________
 ##STR95##                                                                
                                     λmax                          
No.                                                                       
   R    R.sup.1                                                           
          R.sup.2                                                         
               K                 Hue (nm)                                 
__________________________________________________________________________
 1 H CH.sub.3 Cl                                                          
        H H Cl                                                            
          SO.sub.2 C.sub.6 H.sub.5 SO.sub.2 C.sub.6 H.sub.5 Cl            
                ##STR96##        orange orange orange                     
 4 H CH.sub.3                                                             
        Cl Cl                                                             
          SO.sub.2 C.sub.6 H.sub.5 SO.sub.2 C.sub.6 H.sub.5               
                ##STR97##        orange orange                            
 6 Cl Cl                                                                  
        Cl H                                                              
          Cl SO.sub.2 C.sub.6 H.sub.5                                     
                ##STR98##        orange orange                            
 8 H H H                                                                  
        H H H                                                             
          COCH.sub.3 CF.sub.3 COC.sub.6 H.sub.5                           
                ##STR99##        orange orange orange                     
11 12 13                                                                  
   H H F                                                                  
        H H H                                                             
          COC.sub.6 H.sub.5 COCH.sub.3 Br                                 
                ##STR100##       orange orange orange                     
14 15                                                                     
   Br Cl                                                                  
        H H                                                               
          F F                                                             
                ##STR101##       orange orange                            
16 17 18 19                                                               
   H Cl SO.sub.2 C.sub.4 H.sub.9 Cl                                       
        Cl H H Cl                                                         
          Cl SO.sub.2 C.sub.4 H.sub.9 Cl Cl                               
                ##STR102##       orange orange orange orange              
                                     425                                  
20 21                                                                     
   Cl Cl                                                                  
        Cl H                                                              
          Cl CH.sub.3                                                     
                ##STR103##       orange orange                            
                                     425                                  
__________________________________________________________________________
 
    
     
                       TABLE 8                                                     
______________________________________                                    
 ##STR104##                                                               
                                    λmax                           
No.  R.sup.1           R.sup.2      (nm)                                  
______________________________________                                    
      ##STR105##       C.sub.6 H.sub.5                                    
                                    432                                   
2                                                                         
      ##STR106##                                                          
                        ##STR107##  433                                   
3                                                                         
      ##STR108##                                                          
                        ##STR109##  432                                   
4                                                                         
      ##STR110##                                                          
                        ##STR111##  435                                   
5                                                                         
      ##STR112##                                                          
                        ##STR113##  435                                   
6                                                                         
      ##STR114##                                                          
                        ##STR115##  434                                   
7                                                                         
      ##STR116##       C.sub.6 H.sub.5                                    
                                    430                                   
8                                                                         
      ##STR117##                                                          
                        ##STR118##  432                                   
9                                                                         
      ##STR119##                                                          
                        ##STR120##  430                                   
10                                                                        
      ##STR121##                                                          
                        ##STR122##  430                                   
11                                                                        
      ##STR123##       C.sub.6 H.sub.5                                    
                                    430                                   
12                                                                        
      ##STR124##                                                          
                        ##STR125##  435                                   
13                                                                        
      ##STR126##                                                          
                        ##STR127##  431                                   
______________________________________                                    
 
    
     EXAMPLE 5 
     19.5 parts of 2,4-dichloroaniline-5-sulfonic acid are stirred overnight with 50 parts of 15% strength hydrochloric acid in the presence of a wetting agent which is effective under acidic conditions. Thereafter, the mixture is cooled with ice to 0° C., 27 parts by volume of a 23% strength sodium nitrite solution are added in the course of from 5 to 20 minutes, and the suspension is stirred for a further 3 hours at from 0° to 5° C. A solution or suspension of 21.2 parts of 2,6-bis-(3-hydroxypropylamino)-3-cyano-4-methylpyridine in 120 parts by volume of water and 7 parts by volume of concentrated hydrochloric acid is then run in. Stirring is continued for from 15 to 30 minutes, and the pH of the mixture is then slowly increased to 1-1.5 by adding sodium hydroxide solution or sodium formate. The acid formed as a result of the coupling reaction is then bound continuously by adding appropriate amounts of sodium hydroxide solution or sodium formate. When the mixture has been kept at pH 1-1.5 for about 30-60 minutes, the pH is increased to 3-3.5 by adding dilute sodium hydroxide solution or sodium acetate. The coupling reaction quickly comes to an end. The resulting dye of the formula ##STR128## is precipitated virtually quantitatively by adding 40 parts of sodium chloride and is then isolated by filtration. After drying, 44 parts of a brown powder are obtained. 
     The dye dissolves in water to give a yellow solution and dyes nylon and wool in intense, lightfast, golden yellow hues. 
     The absorption maximum of a solution of about 0.020 part of the dye in 900 parts by volume of dimethylformamide and 150 parts by volume of glacial acetic acid is 457 nm (water: 435 nm). 
     
                       TABLE 9                                                     
______________________________________                                    
 ##STR129##                                                               
No.  R.sup.1          R.sup.2      λmax (nm)                       
______________________________________                                    
      ##STR130##      C.sub.6 H.sub.5                                     
                                   459                                    
2                                                                         
      ##STR131##                                                          
                       ##STR132##  459                                    
3                                                                         
      ##STR133##                                                          
                       ##STR134##  459                                    
4                                                                         
      ##STR135##                                                          
                       ##STR136##  460                                    
5                                                                         
      ##STR137##                                                          
                       ##STR138##  460                                    
6                                                                         
      ##STR139##                                                          
                       ##STR140##  460                                    
7                                                                         
      ##STR141##      C.sub.6 H.sub.5                                     
                                   456                                    
8                                                                         
      ##STR142##                                                          
                       ##STR143##  459                                    
9                                                                         
      ##STR144##                                                          
                       ##STR145##  457                                    
10                                                                        
      ##STR146##                                                          
                       ##STR147##  457                                    
11                                                                        
      ##STR148##      C.sub.6 H.sub.5                                     
                                   458                                    
12                                                                        
      ##STR149##                                                          
                       ##STR150##  460                                    
13                                                                        
      ##STR151##                                                          
                       ##STR152##  458                                    
______________________________________                                    
 
    
     
                                           TABLE 10                                
__________________________________________________________________________
 ##STR153##                                                               
No.                                                                       
   R  R.sup.1    R.sup.2    R.sup.3                                       
                               Hue     λmax (nm)                   
__________________________________________________________________________
 1 Cl H          C.sub.3 H.sub.6 OCH.sub.3                                
                            C.sub.3 H.sub.7                               
                               yellow  446                                
 2 Cl H          C.sub.3 H.sub.6 OH                                       
                            C.sub.3 H.sub.7                               
                               yellow  446                                
 3 Cl H          C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH                      
                            CH.sub.3                                      
                               yellow  441                                
 4 Cl H          C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH                      
                            H  yellow  443                                
 5 Cl H          C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH                      
                            CH.sub.3                                      
                               yellow  443                                
 6 Cl H          C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OCH.sub.3               
                            CH.sub.3                                      
                               yellow  444                                
 7 Cl H          C.sub.2 H.sub.4 OC.sub.4 H.sub.9 (n)                     
                            CH.sub.3                                      
                               yellow  446                                
  8                                                                       
   Cl H          C.sub.3 H.sub.6 OCH.sub.3                                
                            CH.sub.3                                      
                               yellow  446                                
 9 Cl H          C.sub.3 H.sub.6 OC.sub.2 H.sub.5                         
                            CH.sub.3                                      
                               yellow  446                                
10 Cl C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH                                 
                 H          CH.sub.3                                      
                               yellow  448                                
11 Cl C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OC.sub.2 H.sub.5                   
                 H          CH.sub.3                                      
                               yellow  449                                
12 Cl C.sub.2 H.sub.5                                                     
                 C.sub.2 H.sub.4 OH                                       
                            CH.sub.3                                      
                               golden yellow                              
                                       455                                
13 Cl CH.sub.3   C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH                      
                            CH.sub.3                                      
                               golden yellow                              
                                       454                                
14 Cl C.sub.2 H.sub.5                                                     
                 C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH                      
                            CH.sub.3                                      
                               golden yellow                              
                                       455                                
15 Cl C.sub.2 H.sub.5                                                     
                 C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH                      
                            CH.sub.3                                      
                               golden yellow                              
                                       453                                
16 Cl CH.sub.2 CHCH.sub.2                                                 
                 C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH                      
                            CH.sub.3                                      
                               golden yellow                              
                                       454                                
17 Cl CH(CH.sub.3).sub.2                                                  
                 C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH                      
                            CH.sub.3                                      
                               golden yellow                              
                                       453                                
18 Cl CH.sub.2 CH.sub.2 OCH.sub.3                                         
                 CH.sub.2 CH.sub.2 OCH.sub.3                              
                            CH.sub.3                                      
                               golden yellow                              
                                       454                                
19 Cl (CH.sub.2).sub.3 OCH.sub.3                                          
                 CH.sub.2 CH.sub.2 OCH.sub.3                              
                            CH.sub.3                                      
                               golden yellow                              
                                       455                                
20 Cl (CH.sub.2).sub.3 OCH.sub.3                                          
                 (CH.sub.2).sub.3 OCH.sub.3                               
                            CH.sub.3                                      
                               golden yellow                              
                                       456                                
21 Cl                                                                     
       ##STR154##                                                         
                 C.sub.2 H.sub.4 OCH.sub.3                                
                            CH.sub.3                                      
                               golden yellow                              
                                       455                                
22 Cl CH.sub.2 CH.sub.2 OCH.sub.3                                         
                 (CH.sub.2).sub.3 OCH.sub.3                               
                            CH.sub.3                                      
                               golden yellow                              
                                       455                                
23 Cl CH.sub.2 CH.sub.2 OCH.sub.3                                         
                 CH.sub.2 CH.sub.2 OH                                     
                            CH.sub.3                                      
                               golden yellow                              
                                       453                                
24 Cl CH.sub.2 CH.sub.2 OCH.sub.3                                         
                  ##STR155##                                              
                            CH.sub.3                                      
                               golden yellow                              
                                       453                                
25 Cl CH.sub.2 CH.sub.2 OCH.sub.3                                         
                 CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                       
                            CH.sub.3                                      
                               golden yellow                              
                                       452                                
26 Cl CH.sub.2 CH.sub.2 OCH.sub.3                                         
                 (CH.sub.2).sub.3 OCH(CH.sub.3).sub.2                     
                            CH.sub.3                                      
                               golden yellow                              
                                       454                                
27 Cl CH.sub.2 CH.sub.2 OCH.sub.3                                         
                 (CH.sub.2).sub.3 O(CH.sub.2).sub.4 OH                    
                            CH.sub.3                                      
                               golden yellow                              
                                       454                                
28 Cl CH.sub.2 CH.sub.2 OCH.sub.3                                         
                 (CH.sub.2).sub.3 OH                                      
                            CH.sub.3                                      
                               golden yellow                              
                                       454                                
29 Cl                                                                     
       ##STR156##                                                         
                 CH.sub.2 CH.sub.2 OCH.sub.3                              
                            CH.sub.3                                      
                               golden yellow                              
                                       452                                
30 Cl                                                                     
       ##STR157##                                                         
                 (CH.sub.2).sub.3 OCH.sub.3                               
                            CH.sub.3                                      
                               orange  453                                
31 Cl                                                                     
       ##STR158##                                                         
                 (CH.sub.2).sub.2 OH                                      
                            CH.sub.3                                      
                               golden yellow                              
                                       452                                
32 Cl                                                                     
       ##STR159##                                                         
                 (CH.sub.2).sub.3 OH                                      
                            CH.sub.3                                      
                               orange  453                                
33 Cl                                                                     
       ##STR160##                                                         
                 (CH.sub.2).sub.3 OC.sub.2 H.sub.5                        
                            CH.sub.3                                      
                               orange  453                                
34 Cl                                                                     
       ##STR161##                                                         
                  ##STR162##                                              
                            CH.sub.3                                      
                               orange  453                                
35 Cl (CH.sub.2).sub.3 OH                                                 
                 (CH.sub.2).sub.2 OH                                      
                            CH.sub.3                                      
                               golden yellow                              
                                       452                                
36 Cl (CH.sub.2).sub.3 OH                                                 
                  ##STR163##                                              
                            CH.sub.3                                      
                               golden yellow                              
                                       455                                
37 Cl (CH.sub.2).sub.3 OH                                                 
                 (CH.sub.2).sub.2 OCH.sub.3                               
                            CH.sub.3                                      
                               golden yellow                              
                                       453                                
38 Cl (CH.sub. 2).sub.3 OH                                                
                 (CH.sub.2).sub.3 OCH.sub.3                               
                            CH.sub.3                                      
                               golden yellow                              
                                       456                                
39 Cl (CH.sub.2).sub.3 OH                                                 
                 (CH.sub.2).sub.3 OC.sub.2 H.sub.5                        
                            CH.sub.3                                      
                               golden yellow                              
                                       456                                
40 Cl (CH.sub.2).sub.2 OH                                                 
                 (CH.sub.2).sub.2 OH                                      
                            CH.sub.3                                      
                               golden yellow                              
                                       452                                
41 Cl (CH.sub.2).sub.2 OH                                                 
                 (CH.sub.2).sub.3 OH                                      
                            CH.sub.3                                      
                               golden yellow                              
                                       453                                
42 Cl (CH.sub.2).sub.2 OH                                                 
                  ##STR164##                                              
                            CH.sub.3                                      
                               golden yellow                              
                                       453                                
43 Cl (CH.sub.2).sub.2 OH                                                 
                 (CH.sub.2).sub.2 OCH.sub.3                               
                            CH.sub.3                                      
                               golden yellow                              
                                       451                                
44 Cl (CH.sub.2).sub.2 OH                                                 
                 (CH.sub.2).sub.2 OCH.sub.3                               
                            CH.sub.3                                      
                               golden yellow                              
                                       453                                
45 Cl (CH.sub.2).sub.2 OH                                                 
                 (CH.sub.2).sub.3 OC.sub.2 H.sub.5                        
                            CH.sub.3                                      
                               golden yellow                              
                                       453                                
46 Cl (CH.sub.2).sub.2 OH                                                 
                 C.sub.4 H.sub.9 (n)                                      
                            CH.sub.3                                      
                               golden yellow                              
                                       456                                
47 Cl (CH.sub.2).sub.2 OH                                                 
                 (CH.sub.2).sub.3 OCH.sub.2 C.sub.6 H.sub.5               
                            CH.sub.3                                      
                               golden yellow                              
                                       455                                
48 Cl (CH.sub.2).sub.2 OH                                                 
                 (CH.sub.2).sub.2 C.sub.6 H.sub. 5                        
                            Ch.sub.3                                      
                               golden yellow                              
                                       450                                
49 Cl (CH.sub.2).sub.2 OH                                                 
                  ##STR165##                                              
                            CH.sub.3                                      
                               golden yellow                              
                                       455                                
50 Cl (CH.sub.2).sub.2 OH                                                 
                  ##STR166##                                              
                            CH.sub.3                                      
                               golden yellow                              
                                       454                                
51 Cl C.sub.2 H.sub.5                                                     
                  ##STR167##                                              
                            CH.sub.3                                      
                               golden yellow                              
                                       451                                
52 Cl C.sub.2 H.sub.5                                                     
                 C.sub.2 H.sub.5                                          
                            CH.sub.3                                      
                               golden yellow                              
                                       449                                
53 Cl (CH.sub.2).sub.2 CN                                                 
                 (CH.sub.2).sub.3 OH                                      
                            CH.sub.3                                      
                               golden yellow                              
                                       450                                
54 Cl (CH.sub.2).sub.5 CN                                                 
                 (CH.sub.2).sub.3 OH                                      
                            CH.sub.3                                      
                               golden yellow                              
                                       457                                
55 Cl (CH.sub.2).sub.2 C.sub.6 H.sub.5                                    
                 (CH.sub.2).sub.2 OH                                      
                            CH.sub.3                                      
                               golden yellow                              
                                       448                                
56 Cl                                                                     
       ##STR168##                                                         
                 C.sub.4 H.sub.9 (n)                                      
                            CH.sub.3                                      
                               golden yellow                              
                                       450                                
57 Cl CH.sub.2 CHCH.sub. 2                                                
                 (CH.sub.2).sub.2 OH                                      
                            CH.sub.3                                      
                               golden yellow                              
                                       452                                
58 Cl CH.sub.2 CHCH.sub.2                                                 
                 (CH.sub.2).sub.3 OH                                      
                            CH.sub.3                                      
                               golden yellow                              
                                       454                                
59 Br (CH.sub.2).sub.3 OH                                                 
                 (CH.sub.2).sub.3 OH                                      
                            CH.sub.3                                      
                               golden yellow                              
                                       457                                
60 CF.sub.3                                                               
      (CH.sub.2).sub.3 OH                                                 
                 (CH.sub.2).sub.3 OH                                      
                            CH.sub.3                                      
                               golden yellow                              
                                       458                                
61 CF.sub.3                                                               
      (CH.sub.2).sub.2 OCH.sub.3                                          
                 (CH.sub.2).sub.2 OH                                      
                            CH.sub.3                                      
                               golden yellow                              
                                       456                                
62 Cl                                                                     
       ##STR169##                                                         
                 (CH.sub.2).sub.2 OH                                      
                            CH.sub.3                                      
                               golden yellow                              
                                       453                                
63 Cl                                                                     
       ##STR170##                                                         
                 (CH.sub.2).sub.3 OH                                      
                            CH.sub.3                                      
                               golden yellow                              
                                       454                                
64 Cl                                                                     
       ##STR171##                                                         
                 (CH.sub.2).sub.3 OH                                      
                            CH.sub.3                                      
                               golden yellow                              
                                       455                                
65 Cl                                                                     
       ##STR172##                                                         
                 (CH.sub.2).sub.2 OH                                      
                            CH.sub.3                                      
                               golden yellow                              
                                       454                                
66 Cl (CH.sub.2).sub.2 OCOCH.sub.3                                        
                 (CH.sub.2).sub.2 OCOCH.sub.3                             
                            CH.sub.3                                      
                               golden yellow                              
                                       450                                
67 Cl (CH.sub.2).sub.3 OCHO                                               
                 (CH.sub.2).sub.3 OCHO                                    
                            CH.sub.3                                      
                               golden yellow                              
                                       454                                
68 Cl (CH.sub.2).sub.2 OCH.sub.3                                          
                 (CH.sub.2).sub.3 OCHO                                    
                            CH.sub.3                                      
                               golden yellow                              
                                       453                                
69 Cl (CH.sub.2).sub.3 OCHO                                               
                 (CH.sub.2).sub.2 OCH.sub.3                               
                            CH.sub.3                                      
                               golden yellow                              
                                       453                                
70 Cl (CH.sub.2).sub.4 OH                                                 
                 (CH.sub.2).sub.4 OH                                      
                            CH.sub.3                                      
                               golden yellow                              
                                       457                                
71 Cl (CH.sub.2).sub.4 OH                                                 
                 (CH.sub.2).sub.3 OH                                      
                            CH.sub.3                                      
                               golden yellow                              
                                       457                                
72 Cl (CH.sub.2).sub.4 OH                                                 
                 (CH.sub.2).sub.2 OH                                      
                            CH.sub.3                                      
                               golden yellow                              
                                       456                                
73 Cl (CH.sub.2).sub.4 OH                                                 
                 (CH.sub.2).sub.2 OCH.sub.3                               
                            CH.sub.3                                      
                               golden yellow                              
                                       456                                
74 Cl C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OCH.sub.3                          
                  ##STR173##                                              
                            CH.sub.3                                      
                               orange  459                                
75 Cl C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OCH.sub.3                          
                 C.sub.6 H.sub.5                                          
                            CH.sub.3                                      
                               orange  458                                
76 Cl C.sub.3 H.sub.5 (OC.sub.2 H.sub.4).sub.2 OCH.sub.3                  
                 C.sub.6 H.sub.5                                          
                            CH.sub.3                                      
                               orange  458                                
77 Cl C.sub.3 H.sub.6 (OC.sub.2 H.sub.4).sub.2 OCH.sub.3                  
                  ##STR174##                                              
                            CH.sub.3                                      
                               orange  460                                
78 Cl C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH                                 
                  ##STR175##                                              
                            CH.sub.3                                      
                               orange  458                                
79 Cl C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH                                 
                 C.sub.6 H.sub.5                                          
                            CH.sub.3                                      
                               orange  457                                
80 Cl C.sub.6 H.sub.5                                                     
                 C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH                      
                            CH.sub.3                                      
                               orange  456                                
81 Cl                                                                     
       ##STR176##                                                         
                 C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH                      
                            CH.sub.3                                      
                               orange  458                                
82 Cl                                                                     
       ##STR177##                                                         
                 C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH                      
                            CH.sub.3                                      
                               orange  458                                
83 Cl                                                                     
       ##STR178##                                                         
                 C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH                      
                            CH.sub.3                                      
                               orange  458                                
__________________________________________________________________________
 
    
     
                                           TABLE 11                                
__________________________________________________________________________
 ##STR179##                                                               
                                               λmax                
No.                                                                       
   R  R.sup.1      R.sup.2   R.sup.3   Hue     (nm)                       
__________________________________________________________________________
 1 Cl C.sub.3 H.sub.6 OH                                                  
                   C.sub.6 H.sub.5                                        
                             C.sub.2 H.sub.4 OH                           
                                       golden yellow                      
                                               435                        
 2 Cl C.sub.3 H.sub.6 OH                                                  
                   C.sub.6 H.sub.5                                        
                             C.sub.2 H.sub.4 OCH.sub.3                    
                                       golden yellow                      
                                               433                        
 3 Cl C.sub.3 H.sub.6 OH                                                  
                   C.sub.6 H.sub.5                                        
                             C.sub.3 H.sub.6 OCH.sub.3                    
                                       golden yellow                      
                                               436                        
 4 Cl C.sub.3 H.sub.6 OH                                                  
                   C.sub.6 H.sub.5                                        
                             C.sub.2 H.sub.4 OC.sub.2 H.sub.5             
                                       golden yellow                      
                                               434                        
 5 Cl C.sub.3 H.sub.6 OH                                                  
                   C.sub.6 H.sub.5                                        
                             C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH          
                                       yellow  433                        
  6                                                                       
   Cl C.sub.3 H.sub.6 OH                                                  
                   C.sub.6 H.sub.5                                        
                             C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OCH.sub.3   
                                       yellow  433                        
 7 Cl C.sub.3 H.sub.6 OH                                                  
                   C.sub.6 H.sub.5                                        
                             C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OH          
                                       golden yellow                      
                                               435                        
 8 Cl C.sub.3 H.sub.6 OH                                                  
                   C.sub.6 H.sub.5                                        
                             C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH          
                                       golden yellow                      
                                               436                        
 9 Cl C.sub.2 H.sub.4 OH                                                  
                   C.sub.6 H.sub.5                                        
                             C.sub.2 H.sub.4 OCH.sub.3                    
                                       yellow  431                        
10 Cl C.sub.2 H.sub.4 OH                                                  
                   C.sub.6 H.sub.5                                        
                             C.sub.3 H.sub.6 OCH.sub.3                    
                                       yellow  432                        
11 Cl C.sub.2 H.sub.4 OH                                                  
                   C.sub.6 H.sub.5                                        
                             C.sub.3 H.sub.6 OC.sub.3 H.sub.7             
                                       yellow  433                        
12 Cl C.sub.2 H.sub.4 OCH.sub.3                                           
                   C.sub.6 H.sub.5                                        
                             C.sub.2 H.sub.4 OCH.sub.3                    
                                       yellow  431                        
13 Cl C.sub.2 H.sub.4 OCH.sub.3                                           
                   C.sub.6 H.sub.5                                        
                             C.sub.3 H.sub.6 OCH.sub.3                    
                                       yellow  433                        
14 Cl C.sub.3 H.sub.6 OCH.sub.3                                           
                   C.sub.6 H.sub.5                                        
                             C.sub.3 H.sub.6 OCH.sub.3                    
                                       golden yellow                      
                                               434                        
15 Cl                                                                     
       ##STR180##  C.sub.6 H.sub.5                                        
                             C.sub.3 H.sub.4 OCH.sub.3                    
                                       golden yellow                      
                                               435                        
16 Cl                                                                     
       ##STR181##  C.sub.6 H.sub.5                                        
                              ##STR182##                                  
                                       golden yellow                      
                                               436                        
17 Br                                                                     
       ##STR183##  C.sub.6 H.sub.5                                        
                              ##STR184##                                  
                                       golden yellow                      
                                               436                        
18 Br C.sub.3 H.sub.6 OH                                                  
                   C.sub.6 H.sub.6                                        
                             C.sub.3 H.sub.6 OH                           
                                       golden yellow                      
                                               437                        
19 Cl C.sub.3 H.sub.6 OH                                                  
                    ##STR185##                                            
                             C.sub.3 H.sub.6 OH                           
                                       golden yellow                      
                                               436                        
20 Cl C.sub.3 H.sub.6 OH                                                  
                    ##STR186##                                            
                             C.sub.3 H.sub.6 OH                           
                                       golden yellow                      
                                               437                        
21 Cl C.sub.4 H.sub.8 OH                                                  
                   C.sub.6 H.sub.5                                        
                             C.sub.4 H.sub.8 OH                           
                                       golden yellow                      
                                               438                        
22 Cl C.sub.2 H.sub.4 OH                                                  
                    ##STR187##                                            
                             C.sub.2 H.sub.4 OH                           
                                       golden yellow                      
                                               436                        
23 Cl                                                                     
       ##STR188##                                                         
                    ##STR189##                                            
                             C.sub.2 H.sub.4 OH                           
                                       yellow  434                        
24 CF.sub.3                                                               
      C.sub.3 H.sub.6 OH                                                  
                   C.sub.6 H.sub.5                                        
                             C.sub.3 H.sub.6 OH                           
                                       golden yellow                      
                                               439                        
25 CF.sub.3                                                               
      C.sub.3 H.sub.6 OH                                                  
                   C.sub.6 H.sub.5                                        
                             C.sub.2 H.sub.4 OH                           
                                       golden yellow                      
                                               439                        
26 CF.sub.3                                                               
       ##STR190##  C.sub.6 H.sub.5                                        
                             C.sub.2 H.sub.4 OH                           
                                       golden yellow                      
                                               439                        
__________________________________________________________________________
 
    
     
                                           TABLE 12                                
__________________________________________________________________________
 ##STR191##                                                               
No.                                                                       
   A            R.sup.1                                                   
                   R.sup.2 Hue     λmax (nm)                       
__________________________________________________________________________
1  CH.sub.2 CH.sub.2                                                      
                Cl C.sub.2 H.sub.4 OH                                     
                           golden yellow                                  
                                   451                                    
2  (CH.sub.2).sub.3                                                       
                Cl C.sub.2 H.sub.4 OH                                     
                           golden yellow                                  
                                   453                                    
3  (CH.sub.2).sub.3                                                       
                Br C.sub.3 H.sub.6 OH                                     
                           golden yellow                                  
                                   455                                    
4  (CH.sub.2).sub.3                                                       
                Cl C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH                    
                           golden yellow                                  
                                   455                                    
5  (CH.sub.2).sub.3                                                       
                Cl C.sub.2 H.sub.4 OCH.sub.3                              
                           golden yellow                                  
                                   455                                    
6  (CH.sub.2).sub.3                                                       
                Cl C.sub.3 H.sub.6 OCH.sub.3                              
                           golden yellow                                  
                                   456                                    
7  (CH.sub.2).sub.4                                                       
                Cl C.sub.2 H.sub.4 OH                                     
                           golden yellow                                  
                                   453                                    
8  (CH.sub.2).sub.4                                                       
                Cl C.sub.3 H.sub.6 OH                                     
                           golden yellow                                  
                                   456                                    
9  (CH.sub.2).sub.3 O(CH.sub.2).sub.2 O(CH.sub.2).sub.3                   
                Cl C.sub.2 H.sub.4 OH                                     
                           golden yellow                                  
                                   452                                    
10 (CH.sub.2).sub.3 O(CH.sub.2).sub.2 O(CH.sub.2).sub.3                   
                Cl C.sub.3 H.sub.6 OH                                     
                           golden yellow                                  
                                   453                                    
11 (CH.sub.2).sub.3 O(CH.sub.2).sub.4 O(CH.sub.2).sub.3                   
                Cl C.sub.3 H.sub.6 OH                                     
                           golden yellow                                  
                                   453                                    
12 (CH.sub.2).sub.3 O(CH.sub.2).sub.4 O(CH.sub.2).sub.3                   
                Cl C.sub.2 H.sub.4 OCH.sub.3                              
                           golden yellow                                  
                                   452                                    
13 (CH.sub.2).sub.3 O(CH.sub.2).sub.4 O(CH.sub.2).sub.3                   
                Br C.sub.3 H.sub.6 OCH.sub.3                              
                           golden yellow                                  
                                   454                                    
__________________________________________________________________________
 
    
     
                                           TABLE 13                                
__________________________________________________________________________
 ##STR192##                                                               
                                     λmax                          
No.                                                                       
   R.sup.1                                                                
         R.sup.2                                                          
           R.sup.3                                                        
             R.sup.4      R.sup.5                                         
                                 Hue (nm)                                 
__________________________________________________________________________
 1 N(CH.sub.3).sub.2                                                      
         H H CH.sub.2 CH.sub.2 OH                                         
                          CH.sub.2 CH.sub.2 OH                            
                                 orange                                   
 2 N(CH.sub.3).sub.2                                                      
         H Cl                                                             
             CH.sub.2 CH.sub.2 OH                                         
                          CH.sub.2 CH.sub.2 OH                            
                                 orange                                   
                                     430                                  
 3 N(CH.sub.3).sub.2                                                      
         Cl                                                               
           Cl                                                             
             CH.sub.2 CH.sub.2 OH                                         
                          CH.sub.2 CH.sub.2 OH                            
                                 orange                                   
                                     463                                  
 4 N(C.sub.2 H.sub.5).sub.2                                               
         Cl                                                               
           Cl                                                             
             CH.sub.2 CH.sub.2 OH                                         
                          CH.sub.2 CH.sub.2 OH                            
                                 orange                                   
                                     463                                  
 5 N(C.sub.2 H.sub.5).sub.2                                               
         H Cl                                                             
             CH.sub.2 CH.sub.2 OH                                         
                          CH.sub.2 CH.sub.2 OH                            
                                 orange                                   
                                     461                                  
 6 N(C.sub.2 H.sub.5).sub.2                                               
         H Cl                                                             
             C.sub.3 H.sub.6 OH                                           
                          C.sub.3 H.sub.6 OH                              
                                 orange                                   
                                     432                                  
 7 N(CH.sub.3).sub.2                                                      
         Cl                                                               
           Cl                                                             
             C.sub.2 H.sub.4 OCH.sub.3                                    
                          C.sub.3 H.sub.6 OH                              
                                 orange                                   
                                     463                                  
 8 N(CH.sub.3).sub.2                                                      
         Cl                                                               
           Cl                                                             
             C.sub.2 H.sub.4 OCH.sub.3                                    
                          C.sub.2 H.sub.4 OCH.sub.3                       
                                 orange                                   
                                     462                                  
 9 N(CH.sub.3).sub.2                                                      
         Cl                                                               
           Cl                                                             
             C.sub.3 H.sub.6 OCH.sub.3                                    
                          C.sub.3 H.sub.6 OCH.sub.3                       
                                 orange                                   
                                     465                                  
10 N(CH.sub.3).sub.2                                                      
         Cl                                                               
           Cl                                                             
              ##STR193##  C.sub.3 H.sub.6 OCH.sub.3                       
                                 orange                                   
                                     462                                  
11 N(CH.sub.3).sub.2                                                      
         Cl                                                               
           Cl                                                             
              ##STR194##  C.sub.2 H.sub.4 OH                              
                                 orange                                   
                                     461                                  
12 N(CH.sub.3).sub.2                                                      
         Cl                                                               
           Cl                                                             
              ##STR195##  C.sub.2 H.sub.5                                 
                                 orange                                   
                                     466                                  
13 N(CH.sub.3).sub.2                                                      
         Cl                                                               
           Cl                                                             
              ##STR196##                                                  
                           ##STR197##                                     
                                 orange                                   
                                     467                                  
14 N(C.sub.2 H.sub.5).sub.2                                               
         Cl                                                               
           Cl                                                             
              ##STR198##                                                  
                           ##STR199##                                     
                                 orange                                   
                                     467                                  
15 N(C.sub.2 H.sub.5).sub.2                                               
         H H                                                              
              ##STR200##                                                  
                           ##STR201##                                     
                                 orange                                   
                                     453                                  
16 N(C.sub.2 H.sub.5).sub.2                                               
         H H                                                              
              ##STR202##  C.sub.6 H.sub.5                                 
                                 orange                                   
                                     452                                  
17 N(C.sub.2 H.sub.5).sub.2                                               
         H H C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH                          
                          C.sub.6 H.sub.5                                 
                                 orange                                   
                                     452                                  
18 N(CH.sub.3).sub.2                                                      
         H H C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH                          
                          C.sub.6 H.sub.5                                 
                                 orange                                   
                                     452                                  
19 CH.sub.3                                                               
         H Cl                                                             
              ##STR203##  C.sub.6 H.sub.5                                 
                                 orange                                   
                                     444                                  
20 CH.sub.3                                                               
         H Cl                                                             
              ##STR204##                                                  
                           ##STR205##                                     
                                 orange                                   
                                     445                                  
21 N(CH.sub.3).sub.2                                                      
         Cl                                                               
           Cl                                                             
             C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OCH.sub.3                   
                          C.sub.3 H.sub.6 OCH.sub.3                       
                                 orange                                   
                                     465                                  
22 NHC.sub.4 H.sub.9                                                      
         Cl                                                               
           Cl                                                             
              ##STR206##  C.sub.6 H.sub.5                                 
                                 orange                                   
                                     463                                  
__________________________________________________________________________
 
    
     
                       TABLE 14                                                    
______________________________________                                    
 ##STR207##                                                               
                                     λmax                          
No.     R.sup.1 R.sup.2        Hue   (nm)                                 
______________________________________                                    
1       Cl      C.sub.2 H.sub.4 OC.sub.4 H.sub.9                          
                               yellow                                     
                                     426                                  
2       Cl      C.sub.3 H.sub.6 OC.sub.4 H.sub.9                          
                               yellow                                     
                                     427                                  
3       Cl      C.sub.4 H.sub.9 (n)                                       
                               yellow                                     
                                     428                                  
4       Cl      C.sub.3 H.sub.6 OC.sub.2 H.sub.5                          
                               yellow                                     
                                     426                                  
5       Cl      C.sub.3 H.sub.6 OCH.sub.3                                 
                               yellow                                     
                                     427                                  
6       Cl      C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OCH.sub.3                
                               yellow                                     
                                     427                                  
7       CH.sub.3                                                          
                C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OCH.sub.3                
                               yellow                                     
                                     427                                  
8       CH.sub.3                                                          
                C.sub.3 H.sub.6 OCH.sub.3                                 
                               yellow                                     
                                     427                                  
9       CH.sub.3                                                          
                C.sub.3 H.sub.6 OC.sub.2 H.sub.5                          
                               yellow                                     
                                     427                                  
10      CH.sub.3                                                          
                C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OH                       
                               yellow                                     
                                     427                                  
11      Cl      C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH                       
                               yellow                                     
                                     427                                  
12      CH.sub.3                                                          
                C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH                       
                               yellow                                     
                                     427                                  
______________________________________                                    
 
    
     
                       TABLE 15                                                    
______________________________________                                    
 ##STR208##                                                               
                                       λmax                        
No. R.sup.1    R.sup.2  R.sup.3  Hue   (nm)                               
______________________________________                                    
 1 C.sub.2 H.sub.4 OCH.sub.3                                              
               CH.sub.3 CH.sub.3 yellow                                   
                                       418                                
 2 C.sub.2 H.sub.4 OCH.sub.3                                              
               C.sub.2 H.sub.5                                            
                        C.sub.2 H.sub.5                                   
                                 yellow                                   
                                       419                                
 3 C.sub.3 H.sub.6 OCH.sub.3                                              
               C.sub.2 H.sub.5                                            
                        C.sub.2 H.sub.5                                   
                                 yellow                                   
                                       420                                
 4 C.sub.3 H.sub.6 OCH.sub.3                                              
               CH.sub.3 CH.sub.3 yellow                                   
                                       418                                
 5 C.sub.3 H.sub.6 OC.sub.2 H.sub.5                                       
               CH.sub.3 CH.sub.3 yellow                                   
                                       418                                
 6 C.sub.3 H.sub.6 OC.sub.2 H.sub.5                                       
               C.sub.2 H.sub.5                                            
                        C.sub.2 H.sub.5                                   
                                 yellow                                   
                                       420                                
 ##STR209##    C.sub.2 H.sub.5                                            
                        C.sub.2 H.sub.5                                   
                                 yellow                                   
                                       419                                
 ##STR210##    C.sub.2 H.sub.5                                            
                        C.sub.2 H.sub.5                                   
                                 yellow                                   
                                       420                                
 ##STR211##    C.sub.4 H.sub.9 (n)                                        
                        C.sub.4 H.sub.9 (n)                               
                                 yellow                                   
                                       422                                
______________________________________