Oligomeric azo dyes

Details Oligomeric azo dyes Oligomeric azo dyes

1999-09-17

2000-09-05

Powers, Fiona T.

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

Organic compounds

Azo

534689, 534805, 534DIG3, C09B 3564, C09B 6722, C09B 6910, D06P 332

Patent

active

061145122

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to oligomeric azo dyes having an alternating construction made up of diazo components and coupling components, containing in the molecule at least 3 units of the structure I ##STR2## where x is a direct bond, oxygen, sulfur or a bridge member of the formula --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)-alkyl-carbamoyl, sulfamoyl, mono- or di-(C.sub.1 -C.sub.4)-alkyl-sulfamoyl, fluorine, chlorine, bromine, nitro or trifluoromethyl, hydroxysulfonyl or carboxyl, Alk is C.sub.1 -C.sub.4 -alkyl with or without hydroxyl, cyano, mono- or di-(C.sub.1 -C.sub.4)-alkylamino, amino, carboxyl or hydroxysulfonyl substitution and with or without interruption by 1 oxygen atom, and ##STR3## where R.sup.5 is hydrogen, C.sub.1 -C.sub.4 -alkyl with or without hydroxyl, cyano, carboxyl, hydroxysulfonyl, methoxycarbonyl, ethoxycarbonyl or acetoxy substitution, and coupling component of the formula IV ##STR4## where R.sup.6 and R.sup.7 are each independently of the other hydroxyl, amino, morpholino, NHAlk or N(Alk).sub.2, and C.sub.1 -C.sub.4 -alkoxy, 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, --NHAlk or --N(Alk).sub.2, natural or synthetic substrates and also to mixtures comprising the novel dyes.
DE-A 41 24 437 discloses black azo dyes obtained by three successive couplings of 4,4'-diaminodiphenylamine-2-sulfonic acid, resorcinol and aniline onto 1-amino-8-hydroxynaphthalene-3,6-disulfonic acid or the respective coupling product. The stoichiometry chosen in this reference relates to a mixture of different trisazo dyes.
DE-A 27 33 107 describes symmetrical hexakisazo compounds obtained stepwise by coupling of tetrazotized 4,4'-diaminostilbene-2,2'-disulfonic acid with the monoazo dye obtained by coupling o f 1-amino-5-nitrobenzene-2-sulfonic acid and 1-amino-8-hydroxynaphthalene-3,6-disulfonic acid and after reduction of the nitro group of the reaction product and a subsequent diazotization in a third coupling step with resorcinol.
A common feature of these dyes is their unsatisfactory fastness. The wet and perspiration fastnesses are inadequate especially when used as leather dyes.
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

Affiliated with

Also associated with

Rating

Oligomeric azo dyes does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Oligomeric azo dyes, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Oligomeric azo dyes will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2213428