Abstract:
A compound having the formula: ##STR1## where X is hydrogen, chlorine or bromine, B is hydrogen, methyl, ethyl or propyl, and one of the radicals R 1  or R 2  is phenyl which is unsubtituted or mono- or poly-substituted by chlorine, methyl, ethyl, t-butyl, phenoxy, methoxy, ethoxy, propoxy or butoxy, and the other is C 2  -C 8  -alkyl which is unsubstituted or substituted by C 1  -C 8  -alkoxy or phenyl, or is allyl, cyclopentyl, cyclohexyl, methylcyclohexyl, ##STR2## The compounds of formula (I) are used as dyes, preferably for cellulose and cellulose-containing fabrics.

Description:
This application is a continuation of application Ser. No. 454,246, filed Dec. 29, 1982, now abandoned. 
    
    
     SUMMARY OF THE INVENTION 
     Azo dye having either 2-arylamino-5-cyano-6-alkylamino- or 2-alkylamino-5-cyano-6-arylamino-pyridine as coupling component general formula I ##STR3## where X is hydrogen, chlorine or bromine, B is hydrogen, methyl, ethyl or propyl, and one of the radicals R 1  or R 2  is phenyl which is unsubstituted or mono- or poly-substituted by chlorine, methyl, ethyl, t-butyl, phenoxy, methoxy, ethoxy, propoxy or butoxy, and the other is C 2  -C 8  -alkyl which is unsubstituted or substituted by C 1  -C 8  -alkoxy or phenyl, or is allyl, cyclopentyl, cyclohexyl, methylcyclohexyl, ##STR4## 
     DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS 
     Specific examples of alkyl radicals R 1  and R 2  are C 2  H 5 , n--C 3  H 7 , i--C 3  H 7 , n-- or i--C 4  H 9 , n-- or i--C 5  H 11 , n-- or i--C 6  H 13 , n-- or i--C 7  H 15 , n-- or i--C 8  H 17 , C 2  H 4  OCH 3 , C 2  H 4  OC 2  H 5 , C 2  H 4  OC 3  H 7 , C 2  H 4  OC 4  H 9 , (CH 2 ) 3  OCH 3 , C 2  H 4  OCH(CH 3 ) 2 , (CH 2 ) 3  OC 2  H 5 , (CH 2 ) 3  OC 3  H 7 , (CH 2 ) 3  OC 4  H 9 , (CH 2 ) 3  OC 6  H 13 , (CH 2 ) 3  OC 8  H 17 , ##STR5## 
     The compounds of the formula I can be prepared by reacting a diazo compound of an amine of the formula ##STR6## with a coupling component of the formula ##STR7## in a conventional manner. Details may be found in the Examples, in which parts and percentages, unless indicated otherwise, are by weight. 
     The compounds of the formula I are preferably used for fixative printing (known under the tradename DYBLN, cf. eg. German Pat. No. 1,811,796 or U.S. Pat. No. 3,706,525), in which tone-on-tone dyeings can be produced on mixtures of cellulose fibers and polyester. Blue to black dyeings with very good fastness characteristics in comparison with conventional dyes, in particular lightfastness and wetfastness, and also a high stability to live steam, are obtained. 
     Particularly important compounds are those of the formula I a ##STR8## where R 1  and R 2  have the above meanings, but R 2  is preferably ##STR9## and R 1  is preferably ##STR10## always in combination with an unsubstituted or substituted alkyl radical of the type defined, and alkyl is methyl, ethyl or t-butyl. 
     Examples of preferred unsubstituted or substituted radicals R 1  and R 2  are --CH(CH 3 ) 2 , ##STR11## 
     Combinations where R 1  is C 6  H 5  and R 2  is ##STR12## are also preferred. 
    
    
     EXAMPLE 1 
     19.6 parts of the diazo component of the formula ##STR13## are prepared and diazotized with nitrosylsulfuric acid, by the process described in German Pat. No. 2,412,975. The finished diazonium salt solution is then run into a suspension of 31.1 parts of the coupling component of the formula ##STR14## in a mixture of 400 parts of water and 900 parts of ice. About 30% strength sodium formate solution is added to the coupling mixture, until the pH of the suspension has risen to 0.3-0.7, during which time the temperature is kept at below +5° C. by addition of ice. The coupling has ended after about 30 minutes, and the precipitated dye is isolated, washed salt-free and dried, in a conventional manner. 49 parts of a bluish black powder of the formula ##STR15## are obtained. The dye melts at from 225° C. to 230° C. and dyes cotton, polyester and polyester/cotton union fabric in lightfast reddish blue to navy shades. 
     If, instead of the above coupling component, the coupling component mixture formed when 2,6-dichloro-3-cyano-4-methylpyridine is reacted first with 2-methoxyethylamine and then with 2-methoxyaniline, as described in German Pat. No. 2,260,827, is used, the corresponding amount of a dye mixture is obtained which, in addition to the above dye, contains a minor amount of the dye of the formula ##STR16## The mixture melts at from 185° to 229° C., 
     The absorption maximum of a solution of the dye in dimethylformamide (about 10 mg/l) is 589.5 nm. 
     The dye mixture dyes or prints cotton, polyester and polyester/cotton union fabric in highly lightfast clear blue to navy hues at a slightly lower temperature than the pure dyes. The dyeings or prints have good wetfastness, even when the hues are deep, and they are also stable to hot steam. 
     An example of a suitable dyeing method is the procedure described in European Pat. No. 0,012,935, and an example of a suitable printing method is that of German Pat. No. 1,811,796. 
     EXAMPLE 2 
     27.5 parts of the diazo component of the formula ##STR17## are stirred into 200 parts of 96-98% strength sulfuric acid at from 10° to 15° C. The mixture is then cooled to 0°-10° C., and a mixture of 100 parts by volume of glacial acetic acid and 17 parts of propionic acid is added dropwise at this temperature. 33 parts of 42-44% strength nitrosylsulfuric acid solution is then added dropwise at 0°-4° C. in the course of from 20 to 30 minutes, with cooling. The diazotization mixture is subsequently stirred at from 0° to 4° C. for from 31/2 to 4 hours, and is then run, with stirring, into a suspension of 31.1 parts of the mixture of coupling components of the formulae ##STR18## which is described in Example 1, in a mixture of 400 parts of water and 900 parts of ice. 
     After the diazonium salt solution has been added, the pH of the coupling mixture is increased to 0.5-10 with approximately 30% strength sodium formate solution, during which the temperature is kept at from -3° to +5° C. by addition of ice. 
     The reacted coupling mixture is heated to 85° C. with steam and is kept at from 85° to 95° C. for 15-30 minutes, and the precipitated dye is washed salt-free in a conventional manner and dried to give 57 parts of a black powder of the formulae ##STR19## The mixing ratio of the dyes is the same as that of the coupling components used. 
     The dye mixture is soluble in dimethylformamide, giving a blue solution, and dyes or prints cotton, polyester or polyester/cotton union fabric in blue to navy hues. The resulting dyeings or prints have good lightfastness and wetfastness. 
     EXAMPLE 3 
     19.6 parts of the diazo component of the formula ##STR20## are prepared and diazotized by the process described in German Pat. No. 2,412,975. The diazonium salt solution is then run into a suspension of a mixture of 20.6 parts of the coupling component of the formula ##STR21## and 9.8 parts of the coupling component of the formula ##STR22## (which, because of the method of synthesis, each contain a relatively small amount of the 2,6-isomeric coupling component) in a mixture of 400 parts of water and 900 parts of ice. The individual coupling components are prepared from 2,6-dichloro-3-cyano-4-methylpyridine by a method similar to that described in German Pat. No. 2,260,827, by reacting the heterocyclic compound first with the aliphatic amine and then, in a second step, with the aromatic amine. 
     The coupling is brought to completion by a procedure similar to that described in Example 1, and the dye is worked up in a conventional manner. 47.5 parts of dye powder are isolated. A dye mixture is obtained, containing individual components of the formulae ##STR23## and relatively small amounts of ##STR24## 
     The dye mixture melts in the range from 185° to 198° C. and its powder is bluish black and dissolves in dimethylformamide giving a blue solution. 
     Pale dyeings or prints on polyester, cotton or polyester/cotton union fabrics are reddish blue, whilst deeper dyeings are clear navy. 
     The dye mixture dyes polyester and cotton with a good matching of hue. The dyeings have good fastness characteristics in use. 
     The dyes listed in the Tables can be prepared by a procedure similar to that described in the Examples. Where two hues are given for dyeings or prints, the first refers to a lighter dyeing (or print) using about 0.2-0.4% of dye, and the second refers to a dyeing (or print) using not less than 0.8% of dye. 
     
                                           TABLE 1__________________________________________________________________________ ##STR25##No. R.sup.1       R.sup.2        R.sup.3                                Hue__________________________________________________________________________ 4##STR26##    C.sub.6 H.sub.5                            CH.sub.3                                reddish blue navy 5##STR27##    &#34;              &#34;   &#34; 6##STR28##    &#34;              &#34;   &#34; 7##STR29##    &#34;              &#34;   &#34; 8  C.sub.2 H.sub.4 OC.sub.2 H.sub.5             &#34;              &#34;   &#34; 9##STR30##    &#34;              &#34;   &#34;10  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 (n)             &#34;              &#34;   &#34;11  C.sub.2 H.sub.4 OC.sub.4 H.sub.9 (n)             &#34;              &#34;   &#34;12##STR31##    &#34;              &#34;   &#34;13  C.sub.3 H.sub.6 OCH.sub.3             &#34;              &#34;   &#34;14  C.sub.3 H.sub.6 OC.sub.2 H.sub.5             &#34;              &#34;   &#34;15##STR32##    &#34;              &#34;   &#34;16##STR33##    &#34;              &#34;   &#34;17##STR34##    &#34;              &#34;   &#34;18##STR35##              ##STR36##     &#34;   &#34;19##STR37##    &#34;              &#34;   &#34;20##STR38##    &#34;              &#34;   &#34;21##STR39##    &#34;              &#34;   &#34;22  C.sub.2 H.sub.4 OC.sub.2 H.sub.5             &#34;              &#34;   &#34;23  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 (n)             &#34;              &#34;   &#34;24  C.sub.2 H.sub.4 OC.sub.4 H.sub.9 (n)             &#34;              &#34;   &#34;25##STR40##    &#34;              &#34;   &#34;26  C.sub.3 H.sub.6 OCH.sub.3             &#34;              &#34;   blue navy27  C.sub.3 H.sub.6 OC.sub.2 H.sub.5             &#34;              &#34;   &#34;28##STR41##    &#34;              &#34;   &#34;29##STR42##              ##STR43##     &#34;   &#34;30  C.sub.2 H.sub.4 OCH.sub.3             &#34;              &#34;   &#34;31  C.sub.3 H.sub.6 OCH.sub.3             &#34;              &#34;   &#34;32##STR44##    CH.sub.2 CHCH.sub.2                            &#34;   &#34;33##STR45##              ##STR46##     &#34;   &#34;34##STR47##35##STR48##    &#34;              &#34;   &#34;36##STR49##    &#34;              &#34;   &#34;37  C.sub.2 H.sub.4 OC.sub.2 H.sub.5             &#34;              &#34;   &#34;38  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 (n)             &#34;              &#34;   &#34;39  C.sub.2 H.sub.4 OC.sub.4 H.sub.9 (n)             &#34;              &#34;   &#34;40  C.sub.3 H.sub.6 OCH.sub.3             &#34;              &#34;   &#34;41  C.sub.3 H.sub.6 OC.sub.2 H.sub.5             &#34;              &#34;   &#34;42##STR50##    &#34;              &#34;   &#34;43  C.sub.3 H.sub.6 OCH.sub.3              ##STR51##     &#34;   dull blue bluish black44##STR52##    &#34;              &#34;   &#34;45##STR53##    &#34;              &#34;   &#34;46##STR54##              ##STR55##     &#34;   greenish blue bluish black47##STR56##    &#34;              &#34;   &#34;48##STR57##    &#34;              &#34;   &#34;49##STR58##    &#34;              &#34;   &#34;50  C.sub.2 H.sub.4 OC.sub.2 H.sub.5             &#34;              &#34;   &#34;51##STR59##    &#34;              &#34;   &#34;52  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 (n)             &#34;              &#34;   &#34;53  C.sub.2 H.sub.4 OC.sub.4 H.sub.9 (n)             &#34;              &#34;   &#34;54##STR60##    &#34;              &#34;   &#34;55  C.sub.3 H.sub.6 OCH.sub.3             &#34;              &#34;   &#34;56  C.sub.3 H.sub.6 OC.sub.2 H.sub.5             &#34;              &#34;   &#34;57  CH.sub.2 CH.sub.2 OCH.sub.3             &#34;              &#34;   dull blue bluish black58  C.sub.3 H.sub.6 OCH.sub.3             &#34;              H   &#34;59##STR61##              ##STR62##     CH.sub.3                                &#34;60##STR63##    &#34;              &#34;   &#34;61##STR64##    &#34;              &#34;   &#34;62##STR65##    &#34;              &#34;   &#34;63  C.sub.2 H.sub.4 OC.sub.2 H.sub.5             &#34;              &#34;   &#34;64  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 (n)             &#34;              &#34;   &#34;65  C.sub.2 H.sub.4 OC.sub.4 H.sub.9 (n)             &#34;              &#34;   &#34;66##STR66##    &#34;              &#34;   &#34;67  C.sub.3 H.sub.6 OCH.sub.3             &#34;              &#34;   &#34;68  C.sub.3 H.sub.6 OC.sub.2 H.sub.5             &#34;              &#34;   &#34;69  C.sub.2 H.sub.4 OCH.sub.3             &#34;              &#34;   &#34;70  C.sub.3 H.sub.6 OCH.sub.3             &#34;              H   &#34;71  &#34;             &#34;              C.sub.2 H.sub.5                                &#34;72  C.sub.4 H.sub.9 (n)             &#34;              CH.sub.3                                &#34;73  C.sub.3 H.sub.6 OCH.sub. 3              ##STR67##     &#34;   &#34;74##STR68##              ##STR69##     &#34;   bluish grey coal black75##STR70##    &#34;              &#34;   &#34;76##STR71##    &#34;              &#34;   &#34;77##STR72##    &#34;              &#34;   &#34;78  C.sub.2 H.sub.4 OC.sub.2 H.sub.5             &#34;              &#34;   &#34;79  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 (n)             &#34;              &#34;   &#34;80  C.sub.2 H.sub.4 OC.sub.4 H.sub.9 (n)             &#34;              &#34;   &#34;81##STR73##    &#34;              &#34;   &#34;82  C.sub.3 H.sub.6 OCH.sub.3             &#34;              &#34;   &#34;83  C.sub.3 H.sub.6 OC.sub.2 H.sub.5             &#34;              &#34;   &#34;84##STR74##85##STR75##    &#34;              &#34;   &#34;86##STR76##    &#34;              &#34;   &#34;87  C.sub.2 H.sub.4 OCH.sub.3             &#34;              &#34;   &#34;88  C.sub.3 H.sub.6 OCH(CH.sub.3).sub.2             &#34;              &#34;   &#34;89  C.sub.3 H.sub.6 OC.sub.8 H.sub.17 (i)             &#34;              &#34;   &#34;90  C.sub.3 H.sub.6 OCH.sub.3             &#34;              H   &#34;91  &#34;             &#34;              C.sub.2 H.sub.5                                &#34;92  C.sub.3 H.sub.6 OC.sub.2 H.sub.5             &#34;              H   &#34;93##STR77##              ##STR78##     CH.sub.3                                dull blue coal black94##STR79##    &#34;              &#34;   &#34;95##STR80##    &#34;              &#34;   &#34;96##STR81##    &#34;              &#34;   &#34;97  C.sub.2 H.sub.4 OC.sub.2 H.sub.5             &#34;              &#34;   &#34;98##STR82##    &#34;              &#34;   &#34;99  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 (n)             &#34;              &#34;   &#34;100 C.sub.2 H.sub.4 OC.sub.4 H.sub.9 (n)             &#34;              &#34;   &#34;101##STR83##    &#34;              &#34;   &#34;102 C.sub.3 H.sub.6 OCH.sub.3             &#34;              &#34;   &#34;103 C.sub.3 H.sub.6 OC.sub.2 H.sub.5             &#34;              &#34;   &#34;104##STR84##    &#34;              &#34;   &#34;105##STR85##    &#34;              &#34;   &#34;106##STR86##    &#34;              &#34;   &#34;107 C.sub.2 H.sub.4 OCH.sub.3             &#34;              &#34;   &#34;108 C.sub.3 H.sub.6 OCH.sub.3              ##STR87##     &#34;   bluish grey coal black__________________________________________________________________________ 
    
     
                       TABLE 2______________________________________ ##STR88##No.  R.sup.1        R.sup.2       R.sup.3                                 Hue______________________________________109 ##STR89##                ##STR90##    H   blue navy110 ##STR91##     &#34;             &#34;   blue navy111 ##STR92##     &#34;             &#34;   blue navy112 ##STR93##     &#34;             &#34;   blue navy113  C.sub.2 H.sub.4 OC.sub.2 H.sub.5               &#34;             &#34;   blue                                 navy114 ##STR94##     &#34;             &#34;   blue navy115  CH.sub.2 CH.sub.2C.sub.6 H.sub.5               &#34;             &#34;   blue                                 navy116 ##STR95##     &#34;             &#34;   blue navy117  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 (n)               &#34;             &#34;   blue                                 navy118  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 (i)                ##STR96##    H   blue navy119  C.sub.2 H.sub.4 OC.sub.4 H.sub.9 (n)               &#34;             &#34;   blue                                 navy120  C.sub.3 H.sub.6 OCH.sub.3               &#34;             &#34;   blue                                 navy121  C.sub.3 H.sub.6 OC.sub.2 H.sub.5               &#34;             &#34;   blue                                 navy122  C.sub.3 H.sub.6 OC.sub.3 H.sub.7 (n)               &#34;             &#34;   blue                                 navy123  C.sub.3 H.sub.6 OC.sub.8 H.sub.17 (i)               &#34;             &#34;   blue                                 navy124 ##STR97##     &#34;             &#34;   blue navy125 ##STR98##     &#34;             Cl  blue navy126 ##STR99##                ##STR100##   H   blue navy127 ##STR101##    &#34;             Cl  blue128 ##STR102##    &#34;             &#34;    &#34;129 ##STR103##    &#34;             &#34;    &#34;130  C.sub.2 H.sub.4 OC.sub.2 H.sub.5                ##STR104##   H   blue navy131  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 (n)               &#34;             &#34;   blue                                 navy132  C.sub.2 H.sub.4 OC.sub.2 H.sub.7 (i)               &#34;             &#34;   blue                                 navy133  C.sub.2 H.sub.4 OC.sub.4 H.sub.9 (n)               &#34;             &#34;   blue                                 navy134  C.sub.3 H.sub.6 OCH.sub.3               &#34;             &#34;   blue                                 navy135  C.sub.3 H.sub.6 OC.sub.2 H.sub.5               &#34;             &#34;   blue                                 navy136  C.sub.3 H.sub.6 OC.sub.3 H.sub.7 (n)               &#34;             &#34;   blue                                 navy137  C.sub.3 H.sub.6 OC.sub.8 H.sub.17 (i)               &#34;             &#34;   blue                                 navy138 ##STR105##                ##STR106##   &#34;   navy bluish black139 ##STR107##    &#34;             &#34;   navy  bluish black140 ##STR108##    &#34;             &#34;   navy bluish black141 ##STR109##    &#34;             &#34;   navy bluish black142  C.sub.2 H.sub.4 OC.sub.2 H.sub.5               &#34;             &#34;   navy                                 bluish                                 black143  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 (n)                ##STR110##   H   navy bluish black144  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 (i)               &#34;             &#34;   navy                                 bluish                                 black145  C.sub.2 H.sub.4 OC.sub.4 H.sub.9 (n)               &#34;             &#34;   navy                                 bluish                                 black146  C.sub.3 H.sub.6 OCH.sub.3               &#34;             &#34;   navy                                 bluish                                 black147  C.sub.3 H.sub.6 OC.sub.2 H.sub.5               &#34;             &#34;   navy                                 bluish                                 black148  C.sub.3 H.sub.6 OC.sub.3 H.sub.7 (n)               &#34;             &#34;   navy                                 bluish                                 black149  CH(CH.sub.3).sub.2               &#34;             &#34;   blue                                 navy150 ##STR111##                ##STR112##   H   blue navy151 ##STR113##    &#34;             &#34;   blue navy152 ##STR114##    &#34;             &#34;   blue navy153 ##STR115##    &#34;             &#34;   blue navy154  C.sub.2 H.sub.4 OC.sub.2 H.sub.5               &#34;             &#34;   blue                                 navy155  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 (n)               &#34;             &#34;   blue                                 navy156  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 (i)                ##STR116##   H   blue navy157  C.sub.2 H.sub.4 OC.sub.4 H.sub.9 (n)               &#34;             &#34;   blue                                 navy158  C.sub.3 H.sub.6 OCH.sub.3               &#34;             &#34;   blue                                 navy159  C.sub.3 H.sub.6 OC.sub.2 H.sub.5               &#34;             &#34;   blue                                 navy160  C.sub.3 H.sub.6 OC.sub.3 H.sub.7 (n)               &#34;             &#34;   blue                                 navy161  C.sub.3 H.sub.6 OC.sub.8 H.sub.17 (i)               &#34;             &#34;   blue                                 navy162 ##STR117##                ##STR118##   &#34;   navy163 ##STR119##    &#34;             &#34;    &#34;164 ##STR120##                ##STR121##   &#34;   greenish  blue navy165 ##STR122##    &#34;             &#34;   greenish blue navy166 ##STR123##    &#34;             &#34;   greenish blue navy167 ##STR124##    &#34;             &#34;   greenish blue navy168  C.sub.2 H.sub.4 OC.sub.2 H.sub.5               &#34;             &#34;   greenish                                 blue                                 navy169 ##STR125##                ##STR126##   H   greenish blue navy170  CH.sub.2 CH.sub.2C.sub.6 H.sub.5               &#34;             &#34;   greenish                                 blue                                 navy171 ##STR127##    &#34;             &#34;   greenish blue navy172  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 (n)               &#34;             &#34;   greenish                                 blue                                 navy173  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 (i)               &#34;             &#34;   greenish                                 blue                                 navy174  C.sub.2 H.sub.4 OC.sub.4 H.sub.9 (n)               &#34;             &#34;   greenish                                 blue                                 navy175  C.sub.3 H.sub.6 OCH.sub.3               &#34;             &#34;   greenish                                 blue                                 navy176  C.sub.3 H.sub.6 OC.sub.2 H.sub.5               &#34;             &#34;   greenish                                 blue                                 navy177  C.sub.3 H.sub.6 OC.sub.3 H.sub.7 (n)               &#34;             &#34;   greenish                                 blue                                 navy178  C.sub.3 H.sub.6 OC.sub.8 H.sub.17 (i)               &#34;             &#34;   greenish                                 blue                                 navy179 ##STR128##    &#34;             &#34;   greenish blue navy180  C.sub.2 H.sub.4 OCH.sub.3               &#34;             &#34;   greenish                                 blue                                 navy181 ##STR129##                ##STR130##   &#34;   blue navy182 ##STR131##    &#34;             &#34;   blue navy183 ##STR132##                ##STR133##   H   blue navy184 ##STR134##    &#34;             &#34;   blue navy185  C.sub.2 H.sub.4 OC.sub.2 H.sub.5               &#34;             &#34;   blue                                 navy186  CH.sub.2 CH.sub.2C.sub.6 H.sub.5               &#34;             &#34;   blue                                 navy187 ##STR135##    &#34;             &#34;   blue navy188  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 (n)               &#34;             &#34;   blue                                 navy189  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 (i)               &#34;             &#34;   blue                                 navy190  C.sub.2 H.sub.4 OC.sub.4 H.sub.9 (n)               &#34;             &#34;   blue                                 navy191  C.sub.3 H.sub.6 OCH.sub.3               &#34;             &#34;   blue                                 navy192  C.sub.3 H.sub.6 OC.sub.2 H.sub.5               &#34;             &#34;   blue                                 navy193  C.sub.3 H.sub.6 OC.sub.3 H.sub.7 (n)               &#34;             &#34;   blue                                 navy194  C.sub.3 H.sub.6 OC.sub.8 H.sub.17 (i)               &#34;             &#34;   blue                                 navy195 ##STR136##    &#34;             &#34;   blue navy196  C.sub.2 H.sub.4 OCH.sub.3               &#34;             &#34;   blue                                 navy197 ##STR137##                ##STR138##   H   blue navy198 ##STR139##                ##STR140##   &#34;   blue navy199 ##STR141##    &#34;             &#34;   blue navy200 ##STR142##    &#34;             &#34;   blue navy201 ##STR143##    &#34;             &#34;   blue navy202  C.sub.2 H.sub.4 OC.sub.2 H.sub.5               &#34;             &#34;   blue                                 navy203  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 (n)               &#34;             &#34;   blue                                 navy204  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 (i)               &#34;             &#34;   blue                                 navy205  C.sub.2 H.sub.4 OC.sub.4 H.sub.9 (n)               &#34;             &#34;   blue                                 navy206  C.sub.3 H.sub.6 OCH.sub.3               &#34;             &#34;   blue                                 navy207  C.sub.3 H.sub.6 OC.sub.2 H.sub.5               &#34;             &#34;   blue                                 navy208  C.sub.3 H.sub.6 OC.sub.3 H.sub.7 (n)               &#34;             &#34;   blue                                 navy209  C.sub.3 H.sub.6 OC.sub.8 H.sub.17 (i)               &#34;             &#34;   blue                                 navy210 ##STR144##                ##STR145##   H   navy211  &#34;              C.sub.3 H.sub.6 OCH.sub.3                             &#34;    &#34;212 ##STR146##                ##STR147##   &#34;   blue navy213 ##STR148##    &#34; 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