TREA

Heterocyclic azo dyes containing cyanothiophene derivatives as diazo components and diaminopyridines as coupling components

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Information

  • Patent Grant
  • 4965346
  • Patent Number
    4,965,346
  • Date Filed
    Thursday, March 16, 1989
    35 years ago
  • Date Issued
    Tuesday, October 23, 1990
    33 years ago
Information
Abstract
The novel dyes of the general formula I ##STR1## where X is hydrogen or C.sub.1-C.sub.4 -alkyl or is phenyl which is unsubstituted or substituted by fluorine, chlorine, bromine, methyl, methoxy or nitro, Y is cyano, a carboxylic ester group or nitro, Z is cyano, acetyl, benzoyl or unsubstituted or substituted carbamyl, or X and Z or Y and Z may simultaneously be a carboxylic ester group, and R.sup.1 and R.sup.2 independently of one another are each hydrogen or unsubstituted or substituted alkyl or aryl, are very useful for dyeing polyesters, polyester/cellulose blends or thermoplastics.
Description
Claims
  • 1. A compound of formula I ##STR47## where X.sub.1 is hydrogen or methyl; Y.sub.1 is COOCH.sub.3, COOC.sub.2 H.sub.5, COOC.sub.3 H.sub.7, COOC.sub.4 H.sub.9 or COOC.sub.2 H.sub.4 OCH.sub.3 and
  • B.sup.1 and B.sup.2 independently of one another are each hydrogen or
  • (i) C.sub.2 -C.sub.8 -alkyl which is unsubstituted;
  • (ii) C.sub.2 -C.sub.8 -alkyl which is substituted by hydroxyl, C.sub.1 -C.sub.8 -alkanoyloxy, C.sub.1 -C.sub.4 -alkoxy, benzyloxy, or phenoxy;
  • (iii) C.sub.2 -C.sub.8 -alkyl which is interrupted by oxygen, exclusive of (ii); or
  • (iv) C.sub.2 -C.sub.8 -alkyl which is interrupted by oxygen and substituted by hydroxy, C.sub.1 -C.sub.8 -alkanoyloxy, C.sub.1 -C.sub.4 -alkoxy, benzyloxy or phenoxy, exclusive of (ii) and (iii).
  • 2. The compound of claim 1, where X is methyl.
  • 3. The compound of claim 1, where one of the radicals B.sup.1 and B.sup.2 is hydrogen and the other is C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OCOCH.sub.3, C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OCOC.sub.2 H.sub.5, C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH, C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OCOCH.sub.3, C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OCOC.sub.2 H.sub.5, C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OCH.sub.3, C.sub.2 H.sub.4 OC.sub.2 H.sub.5, C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OC.sub.4 H.sub.9, C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OC.sub.2 H.sub.5, C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OC.sub.4 H.sub.9, C.sub.3 H.sub.6 OCH.sub.2 C.sub.6 H.sub.5, C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OC.sub.6 H.sub.5 or C.sub.3 H.sub.6 OCH.sub.2 -CH(C.sub.2 H.sub.5)C.sub.4 H.sub.9, or where one of the radicals B.sup.1 and B.sup.2 is C.sub.2 H.sub.4 OH, C.sub.3 H.sub.6 OH, C.sub.2 H.sub.4 OCOCH.sub.3, C.sub.2 H.sub.4 OCOC.sub.2 H.sub.5, C.sub.2 H.sub.4 OCH.sub.3, C.sub.3 H.sub.6 OCH.sub.3, CH(CH.sub.3).sub.2 or C.sub.4 H.sub.9 and the other is C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OCOCH.sub.3, C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH, C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OCHO, C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OCOCH.sub.3, C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OCOC.sub.2 H.sub.5, C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OC.sub.4 H.sub.9, C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OC.sub.2 H.sub.5, C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OC.sub.4 H.sub.9, or where one of the radicals B.sup.1 and B.sup.2 C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OC.sub.6 H.sub.5 is C.sub.2 H.sub.4 OH, C.sub.3 H.sub.6 OH, C.sub.2 H.sub.4 OCOCH.sub.3, C.sub.2 H.sub.4 OCOC.sub.2 H.sub.5, C.sub.3 H.sub.6 OCOCH.sub.3 or C.sub.3 H.sub.6 OCOC.sub.2 H.sub.5 and the other is C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OCH.sub.3, C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OC.sub.2 H.sub.5, C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OC.sub.4 H.sub.9, C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OC.sub.2 H.sub.5, or C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OC.sub.4 H.sub.9.
  • 4. The compound of claim 1, where one of the radicals B.sup.1 and B.sup.2 is hydrogen and the other is C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OCOCH.sub.3, C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OCOC.sub.2 H.sub.5, C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH, C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OCOCH.sub.3, C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OCOC.sub.2 H.sub.5, C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OCH.sub.3, C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OC.sub.2 H.sub.5, C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OC.sub.4 H.sub.9, C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OC.sub.2 H.sub.5, C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OC.sub.4 H.sub.9, C.sub.3 H.sub.6 OCH.sub.2 C.sub.6 H.sub.5, C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OC.sub.6 H.sub.5 or C.sub.3 H.sub.6 OCH.sub.2 -CH(C.sub.2 H.sub.5)C.sub.4 H.sub.9.
  • 5. The compound of claim 1, where one of the radicals B.sup.1 and B.sup.2 is C.sub.2 H.sub.5, C.sub.2 H.sub.4 OCH.sub.3, C.sub.3 H.sub.6 OCH.sub.3, CH(CH.sub.3).sub.2 or C.sub.4 H.sub.9 and the other is C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OCOCH.sub.3, C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH, C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OCHO, C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OCOCH.sub.3, C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OCOC.sub.2 H.sub.5, C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OC.sub.4 H.sub.9, C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OC.sub.2 H.sub.5, C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OC.sub.4 H.sub.9 or C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OC.sub.6 H.sub.5.
  • 6. The compound of claim 1, where one of the radicals B.sup.1 and B.sup.2 is C.sub.2 H.sub.4 OH, C.sub.3 H.sub.6 OH, C.sub.2 H.sub.4 OCOCH.sub.3, C.sub.2 H.sub.4 OCOC.sub.2 H.sub.5, C.sub.3 H.sub.6 OCOCH.sub.3 or C.sub.3 H.sub.6 OCOC.sub.2 H.sub.5 and the other is C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OCH.sub.3, C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OC.sub.2 H.sub.5, C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OC.sub.4 H.sub.9, C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OC.sub.2 H.sub.5, or C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OC.sub.4 H.sub.9.
Priority Claims (1)
Number Date Country Kind
3528759 Aug 1985 DEX
Parent Case Info

This application, Ser. No. 07/324,558 is a divisional application of Ser. No. 07/188,075, filed Apr. 28, 1988, now U.S. Pat. No. 4,855,413, which in turn is a continuation of Ser. No. 07/888,956, filed July 24, 1986 and now abandoned. The present invention relates to compounds of the general formula I ##STR2## where X is hydrogen or C.sub.1 -C.sub.4 -alkyl or is phenyl which is unsubstituted or substituted by fluorine, chlorine, bromine, methyl, methoxy or nitro, Y is cyano, a carboxylic ester group or nitro, Z is cyano, acetyl, benzoyl or unsubstituted or substituted carbamyl, or X and Z or Y and Z may simultaneously be a carboxylic ester group, and R.sup.1 and R.sup.2 independently of one another are each hydrogen or unsubstituted or substituted alkyl or aryl. Examples of substituted carbamyl radicals Z are CONHR.sup.3 or ##STR3## where R.sup.3 is unsubstituted or substituted alkyl or phenyl or cyclohexyl, R.sup.4 is unsubstituted or substituted alkyl and R.sup.3 and R.sup.4 together with the nitrogen may form a heterocyclic ring. Specific examples are CONHCH.sub.3, CONHC.sub.2 H.sub.5, CONH-n-C.sub.3 H.sub.7, CONH-n-C.sub.4 H.sub.9, CONHCH.sub.2 CH(CH.sub.3).sub.2, CONHC.sub.2 H.sub.4 OCH.sub.3, CONHC.sub.3 H.sub.6 OCH.sub.3, CONHC.sub.2 H.sub.4 OH, CONHC.sub.3 H.sub.6 OH, CONHC.sub.6 H.sub.5, CONHC.sub.6 H.sub.4 CH.sub.3, CONHC.sub.6 H.sub.4 OCH.sub.3, CON(CH.sub.3).sub.2, CON(C.sub.2 H.sub.5).sub.2, CON(C.sub.2 H.sub.4 OCH.sub.3).sub.2 and CON(CH.sub.3)C.sub.6 H.sub.5. Preferred carboxylic ester groups Y and, where relevant, X and Z are COOCH.sub.3, COOC.sub.2 H.sub.5, COOC.sub.3 H.sub.7, COOC.sub.4 H.sub.9 and COOC.sub.2 H.sub.4 OCH.sub.3. Examples of radicals R.sup.1 and R.sup.2 in addition to hydrogen are: 1. Unsubstituted or substituted alkyl, such as CH.sub.3, C.sub.2 H.sub.5, n-C.sub.3 H.sub.7, CH(CH.sub.3).sub.2, n-C.sub.4 H.sub.9, CH.sub.2 -CH(CH.sub.3).sub.2, ##STR4## C.sub.2 H.sub.4 OCH.sub.3, C.sub.2 H.sub.4 OC.sub.2 H.sub.5, C.sub.2 H.sub.4 OC.sub.3 H.sub.7, C.sub.2 H.sub.4 OC.sub.4 H.sub.9, C.sub.2 H.sub.4 OC.sub.6 H.sub.5, C.sub.2 H.sub.4 OC.sub.6 H.sub.11, C.sub.2 H.sub.4 CN, C.sub.5 H.sub.10 CN, C.sub.6 H.sub.12 CN, C.sub.2 H.sub.4 OC.sub.2 H.sub.4 CN, C.sub.3 H.sub.6 OC.sub.2 H.sub.4 CN, C.sub.3 H.sub.6 OCH.sub.3, C.sub.3 H.sub.6 OC.sub.2 H.sub.5, C.sub.3 H.sub.6 OC.sub.3 H.sub.7, C.sub.3 H.sub.6 OC.sub.4 H.sub.9, ##STR5## C.sub.3 H.sub.6 OC.sub.6 H.sub.11, C.sub.3 H.sub.6 OC.sub.8 H.sub.17, C.sub.3 H.sub.6 OCH.sub.2 C.sub.6 H.sub.5, C.sub.3 H.sub.6 OC.sub.2 H.sub.4 C.sub.6 H.sub.5, C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OC.sub.6 H.sub.5, C.sub.3 H.sub.6 OC.sub.6 H.sub.5, C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OH, C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH, C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OCH.sub.3, C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OC.sub.2 H.sub.5, C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OCH(CH.sub.3).sub.2, C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OC.sub.4 H.sub.9, C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OCH.sub.2 C.sub.6 H.sub.5, C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OC.sub.6 H.sub.5, C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OCH.sub.3, ##STR6## corresponding radicals which contain two C.sub.2 H.sub.4 O, C.sub.3 H.sub.6 O, ##STR7## groups; and ##STR8## 2. Unsubstituted or substituted cycloalkyl: ##STR9## 3. Unsubstituted or substituted aralkyl: ##STR10## and corresponding groups containing C.sub.6 H.sub.4 CH.sub.3 or C.sub.6 H.sub.4 OCH.sub.3 instead of C.sub.6 H.sub.5. 4. Unsubstituted or substituted phenyl: C.sub.6 H.sub.5, C.sub.6 H.sub.4 CH.sub.3, C.sub.6 H.sub.3 (CH.sub.3).sub.2, C.sub.6 H.sub.4 OCH.sub.3, C.sub.6 H.sub.3 (OCH.sub.3).sub.2, C.sub.6 H.sub.4 Cl and C.sub.6 H.sub.2 (OCH.sub.3).sub.2 Cl. 5. The radicals: CH.sub.2 CH.dbd.CH.sub.2, CH.sub.2 COOCH.sub.3, (CH.sub.2).sub.5 COOCH.sub.3, (CH.sub.2).sub.5 COOC.sub.2 H.sub.5, ##STR11## where n=2, 3, 4 or 6. 6. Acyloxy radicals: (CH.sub.2).sub.2 OCHO, (CH.sub.2).sub.2 OCO(CH.sub.2).sub.n CH.sub.3, (C.sub.2 H.sub.4 O).sub.2 CHO, (C.sub.2 H.sub.4 O).sub.2 CO(CH.sub.2).sub.n CH.sub.3, (CH.sub.2).sub.3 O(CH.sub.2).sub.2 OCHO, (CH.sub.2).sub.3 O(CH.sub.2).sub.2 OCO(CH.sub.2).sub.n CH.sub.3, (CH.sub.2).sub.2 O(CH.sub.2).sub.4 OCHO, and (CH.sub.2).sub.2 O(CH.sub.2).sub.4 OCO(CH.sub.2).sub.n CH.sub.3, where n is from 0 to 7, and ##STR12## (CH.sub.2).sub.2 OCOC.sub.6 H.sub.5, (CH.sub.2).sub.2 OCOC.sub.6 H.sub.4 CH.sub.3, (CH.sub.2).sub.2 OCOC.sub.6 H.sub.4 Cl, (CH.sub.2).sub.2 OCONHCH.sub.3, (CH.sub.2).sub.2 OCONHC.sub.4 H.sub.9, ##STR13## and (CH.sub.2).sub.2 OCONHC.sub.6 H.sub.5, and the corresponding radicals containing (CH.sub.2).sub.3 or (CH.sub.2).sub.4 instead of (CH.sub.2).sub.2. 7. Acyl radicals: CHO, CH.sub.3 (CH.sub.2).sub.n CO, where n is from 0 to 7, C.sub.6 H.sub.5 CO, CH.sub.3 C.sub.6 H.sub.4 CO, C.sub.6 H.sub.5 CH.sub.2 CO, C.sub.6 H.sub.5 OCH.sub.2 CO, CH.sub.3 SO.sub.2, C.sub.2 H.sub.5 SO.sub.2, C.sub.6 H.sub.5 SO.sub.2 and CH.sub.3 C.sub.6 H.sub.4 SO.sub.2. The compounds of the formula I can be prepared by reacting a diazonium compound of an amine of the formula ##STR14## with a coupling component of the formula ##STR15## in a conventional manner. The Examples which follow illustrate the preparation, parts and percentages stated in the Examples being by weight, unless stated otherwise. The .lambda. max values were determined in a mixture of dimethylformamide and glacial acetic acid in a ratio of 9:1. The compounds of the formula I give deep, brilliant and very lightfast dyeings, in particular on polyester. They are also very useful for dyeing thermoplastics, such as polystyrene, polymethacrylate, polycarbonate, nylon and styrene/acrylic acid/butadiene copolymers, since they possess high color strength, lightfastness and thermal stability. Many novel dyes are also useful for dyeing and/or printing polyester/cotton blends in hues which are very lightfast and fast to laundering, by the method described in German Patent 1,811,796. Of particular importance are dyes of the general formula Ia ##STR16## where X.sup.1 is hydrogen, methyl or phenyl, Y.sup.1 is cyano or a carboxylic ester group and B.sup.1 and B.sup.2 independently of one another are each (i) C.sub.2 -C.sub.8 -alkyl which is unsubstituted; (ii) C.sub.2 -C.sub.8 -alkyl which is substituted by hydroxyl, C.sub.1 -C.sub.8 -alkanoyloxy, C.sub.1 -C.sub.4 -alkoxy, benzyloxy, or phenoxy; (iii) C.sub.2 -C.sub.8 -alkyl which is interrupted by oxygen, exclusive of (ii); or (iv) C.sub.2 -C.sub.8 -alkyl which is interrupted by oxygen and substituted by hydroxy, C.sub.1 -C.sub.8 -alkanoyloxy, C.sub.1 -C.sub.4 -alkoxy, benzyloxy, or phenoxy, exclusive of (ii) and (iii); (v) phenyl which is unsubstituted; or (vi) phenyl which is substituted by methyl or methoxyl. Preferred carboxylic ester groups are COOCH.sub.3 and COOC.sub.2 H.sub.5. Examples of particularly preferred radicals B.sup.1 and B.sup.2 are hydrogen and the radicals C.sub.2 H.sub.5, C.sub.3 H.sub.7, C.sub.4 H.sub.9, ##STR17## C.sub.6 H.sub.11, C.sub.6 H.sub.5, C.sub.6 H.sub.4 CH.sub.3, C.sub.6 H.sub.4 OCH.sub.3, C.sub.2 H.sub.4 OH, C.sub.3 H.sub.6 OH, C.sub.2 H.sub.4 OCH.sub.3, C.sub.3 H.sub.6 OCH.sub.3, C.sub.2 H.sub.4 OC.sub.2 H.sub.5, C.sub.2 H.sub.4 OC.sub.4 H.sub.9, C.sub.3 H.sub.6 OC.sub.2 H.sub.5, C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH, C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OH, C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH, C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OCH.sub.3, C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OC.sub.2 H.sub.5, C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OC.sub.4 H.sub.9, C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OC.sub.2 H.sub.5, C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OC.sub.4 H.sub.9, C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OCO(CH.sub.2).sub.m CH.sub.3, C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OCO(CH.sub.2).sub.m CH.sub.3, C.sub. 3 H.sub.6 OC.sub.4 H.sub.8 OCO(CH.sub.2).sub.m CH.sub.3, C.sub.2 H.sub.4 OCO(CH.sub.2).sub.m CH.sub.3, C.sub.3 H.sub.6 OCO(CH.sub.2).sub.m CH.sub.3, C.sub.3 H.sub.6 OCH.sub.2 C.sub.6 H.sub.5 and C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OC.sub.6 H.sub.5, where m is from 1 to 4. Examples of particularly preferred combinations of B.sup.1 and B.sup.2 are hydrogen and C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OCOCH.sub.3, C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OCOC.sub.2 H.sub.5, C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH, C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OCOCH.sub.3, C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OCOC.sub.2 H.sub.5, C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OCH.sub.3, C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OC.sub.2 H.sub.5, C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OC.sub.4 H.sub.9, C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OC.sub.2 H.sub.5, C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OC.sub.4 H.sub.9, C.sub.3 H.sub.6 OCH.sub.2 C.sub.6 H.sub.5, C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OC.sub.6 H.sub.5 or C.sub.3 H.sub.6 OCH.sub.2 --CH(C.sub.2 H.sub.5)C.sub.4 H.sub.9 and C.sub.2 H.sub.5, C.sub.2 H.sub.4 OCH.sub.3, C.sub.3 H.sub.6 OCH.sub.3, CH(CH.sub.3).sub.2 or C.sub.4 H.sub.9 in combination with C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OCOCH.sub.3, C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH, C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OCHO, C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OCOCH.sub.3, C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OCOC.sub.2 H.sub.5, C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OC.sub.4 H.sub.9, C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OC.sub.2 H.sub.5, C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OC.sub.4 H.sub.9 or C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OC.sub.6 H.sub.5 and C.sub.2 H.sub.4 OH, C.sub.3 H.sub.6 OH, C.sub.2 H.sub.4 OCOCH.sub.3, C.sub.2 H.sub.4 OCOC.sub.2 H.sub.5, C.sub.3 H.sub.6 OCOCH.sub.3 or C.sub.3 H.sub.6 OCOC.sub.2 H.sub. 5 combined with C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OCH.sub.3, C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OC.sub.2 H.sub.5, C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OC.sub.4 H.sub.9, C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OC.sub.2 H.sub.5, C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OC.sub.4 H.sub.9, C.sub.6 H.sub.4 OCH.sub.3 or C.sub.6 H.sub.5. The process for the preparation of the 2,6-diaminopyridines which are substituted by acyloxyalkyl or acyloxyalkoxyalkyl and are free of by-products is also particularly important. To date, azo dyes possessing such coupling components have had to be prepared by subsequent acylation of the corresponding hydroxyl-containing dyes in an anhydrous organic solvent with an acyl halide or an anhydride, since the coupling components themselves preferentially undergo N-acylation under these conditions; the N-acyl-2,6-diaminopyridines, however, are not capable of coupling. According to the invention, the coupling components are prepared by adding not less than an equivalent amount of sulfuric acid to a solution or suspension of the hydroxyl-containing substituted pyridine in the desired organic acid and stirring at from 20.degree. to 100.degree. C., preferably from 20.degree. to 50.degree. C. The degree of acylation depends on the water content and reaches 100% in an anhydrous medium. However, the absence of water and 100% conversion are not necessary in every case in order to achieve optimum tinctorial properties. In most cases, a conversion of from 70 to 90% is sufficient; this conversion does not require anhydrous conditions and advantageously permits the acylation to be combined with the preparation of the hydroxyalkylaminopyridine. The coupling components are, as a rule, isomer mixtures in which the substituents in the 2,6-positions are interchanged; however, different amounts of the isomers are present, depending on the preparation.

US Referenced Citations (2)
Number Name Date Kind
3998802 Dehnert et al. Dec 1976
4042578 Dehnert et al. Aug 1977
Foreign Referenced Citations (3)
Number Date Country
201896 Nov 1986 EPX
3528759 Feb 1987 DEX
3615093 Nov 1987 DEX
Divisions (1)
Number Date Country
Parent 188075 Apr 1988
Continuations (1)
Number Date Country
Parent 888956 Jul 1986