Oligomer azo colorants

Details Oligomer azo colorants Oligomer azo colorants

1999-11-01

2000-11-28

Powers, Fiona T.

Organic compounds -- part of the class 532-570 series

Organic compounds

Azo

534685, 534582, 8437, 8919, C09B 3564, C09B 6910, C09B 6722, D06P 332, C09D 1102

Patent

active

061537349

DESCRIPTION:

BRIEF SUMMARY
DESCRIPTION

The present invention relates to oligomeric azo dyes having an alternating construction made up of tetrazo components and coupling components, containing in the molecule at least 2 units of the structure I ##STR1## where n is 1 or 2, --NHCO--, --NHCONH--, --CO--, --NHSO.sub.2 --, --SO.sub.2 NHSO.sub.2 --, --SO.sub.2 --, --SO.sub.2 --NH--A--NH--SO.sub.2 --, --NAlk--CO--, --NAlk--CO--NAlk--, --NAlk--CO--NH--, --NAlk--SO.sub.2 --, --SO.sub.2 --NAlk--SO.sub.2 --, --SO.sub.2 --NAlk--A--NAlk--SO.sub.2 --, --SO.sub.2 --NAlk--A--NH--SO.sub.2 --, --CH.dbd.CH--, --CH.sub.2 CH.sub.2 --, --C(CH.sub.3).sub.2 --, --CH.sub.2 -- or --NH--, -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkanoyl, cyano, carboxyl, hydroxysulfonyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, hydroxyl, carbamoyl, mono- or di-C.sub.1 -C.sub.4 -alkylcarbamoyl, sulfamoyl, mono- or di-C.sub.1 -C.sub.4 -alkylsulfamoyl, fluorine, chlorine, bromine, nitro or trifluoromethyl, hydroxysulfonyl or carboxyl, hydroxyl, di-C.sub.1 -C.sub.4 -alkylamino, amino, carboxyl, hydroxysulfonyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, carbamoyl, mono- or di-C.sub.1 -C.sub.4 -alkylcarbamoyl, sulfamoyl, mono- or di-C.sub.1 -C.sub.4 -alkylsulfamoyl or morpholinylcarbonyl substitution and with or without interruption by 1 oxygen atom, and ##STR2## where R.sup.7 and R.sup.8 are each independently of the other hydroxyl, amino, morpholino, --NHAlk or --N(Alk).sub.2, and -alkoxycarbonyl, carbamoyl, mono- or di-C.sub.1 -C.sub.4 -alkylcarbamoyl, sulfamoyl, mono- or di-C.sub.1 -C.sub.4 -alkylsulfamoyl, --Alk, --OAlk, --NHAlk or --N(Alk).sub.2, natural or synthetic substrates and also to mixtures comprising the novel dyes.
DD-A-244 349 describes black pentakisazo dyes obtained by coupling of tetrazotized 4,4'-diaminophenylamine-2-sulfonic acid onto 2-amino-8-hydroxynaphthalene-6-sulfonic acid, renewed tetrazotization, simple coupling onto 1,3-diaminobenzene-4-sulfonic acid and two successive coupling steps.
DE-A-44 41 232 teaches the coupling of one equivalent of tetrazotized 4,4'-diaminodiphenylamine-2-sulfonic acid onto 2 equivalents of 2-amino-8-hydroxynaphthalene-6-sulfonic acid, subsequent tetrazotization and renewed coupling onto 2 equivalents of 3-hydroxyphenyliminodiacetic acid to form tetrakisazo dyes.
A common feature of these dyes is their unsatisfactory fastness. The wet and perspiration fastnesses are inadequate on leather especially.
It is an object of the present invention to provide novel azo dyes having advantageous application properties, especially good wet and perspiration fastness properties.
We have found that this object is achieved by the oligomeric azo dyes defined at the beginning.
Since the oligomeric azo dyes contain a plurality of hydroxysulfonyl groups and also, optionally, carboxyl groups, their salts are comprehended by the invention, too.
Suitable salts are metal or ammonium salts. Metal salts are especially the lithium, sodium or potassium salts. Ammonium salts for the purposes of the invention are salts having either unsubstituted or substituted ammonium cations. Examples of substituted ammonium cations are monoalkyl-, dialkyl-, trialkyl-, tetraalkyl- or benzyltrialkyl-ammonium cations or cations derived from nitrogenous five- or six-membered saturated heterocycles, such as pyrrolidinium, piperidinium, morpholinium or piperazinium cations or their N-monoalkyl- or N,N-dialkyl-substituted products. Alkyl here is generally to be understood as meaning straight-chain or branched C.sub.1 -C.sub.20 -alkyl with or without substitution by from 1 to 3 hydroxyl groups and with or without interruption by from 1 to 4 oxygen atoms in ether function.
Any substituted alkyl appearing in the abovementioned formulae generally has 1 or 2 substituents, especially one substituent.
The phenylene group A is preferably 1,3- or 1,4-phenylene. If substituted, it generally bears 1 or 2, preferably one, hydroxysulfonyl radical.
R.sup.1, R.sup.2, R.sup.9 and Alk are each for example methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl or tert-butyl.
R.su

REFERENCES:
patent: 5597387 (1997-01-01), Bauer et al.
Patent Abstracts of Japan, vol. 005, No. 024 (C-043), Feb. 13, 1981.

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