Organic compounds -- part of the class 532-570 series – Organic compounds – Azo
Patent
1998-07-06
2000-01-04
Powers, Fiona T.
Organic compounds -- part of the class 532-570 series
Organic compounds
Azo
534642, 562 43, 562 44, 8549, C09B 6208, C09B 62507, D06P 138
Patent
active
060111402
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to novel reactive dyes of the formula I ##STR2## where n is 1 or 2, ##STR3## R.sup.1 is hydrogen or hydroxysulfonylmethyl, R.sup.2 is hydrogen or hydroxyfonlymethyl, and ##STR4## or, when n is 2, a radical of the formula ##STR5## where the ring A may be benzofused, R.sup.3, R.sup.4 and R.sup.5 are each independently of the others hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, halogen or hydroxysulfonyl, E is hydrogen, a heterocyclic anchor radical or a anchor radical of the aliphatic series, Y is vinyl or a radical of the formula C.sub.2 H.sub.4 --Q, where Q is an alkali-detachable group, and T is a bridge member, present in the molecule and that dyes of the formula ##STR6## where n, D and G.sup.2 are each as defined above, shall be excluded, to their use for dyeing or printing hydroxyl-containing or nitrogenous organic substrates and to naphthylamines as intermediates therefor.
The above-excluded dyes and intermediates are known from prior patent application WO 9610610.
It is an object of the present invention to provide novel reactive dyes derived from phenyl- or naphthalene-azo-naphthalene dyes. The novel dyes shall have an advantageous application property profile.
We have found that this object is achieved by the reactive dyes of the formula I defined at the beginning.
The novel reactive dyes of the formula I are each indicated in the form of the free acid, but salts thereof are also encompassed by the claims, of course.
Suitable cations are derived from metal or ammonium ions. Metal ions are in particular the lithium, sodium or potassium ions. Ammonium ions for the purposes of the present invention are substituted or unsubstituted ammonium cations. Substituted ammonium cations include for example 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 is generally to be understood as meaning straight-chain or branched C.sub.1 -C.sub.20 -alkyl which may be substituted by 1 or 2 hydroxyl groups and/or interrupted by from 1 to 4 oxygen atoms in ether function.
Any alkyl or alkylene herein can be straight-chain or branched.
Any substituted alkyl herein generally contains 1 or 2 substituents.
Any substituted phenylene herein contains for example, unless otherwise stated, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, halogen, hydroxysulfonyl, sulfamoyl or mono- or di-C.sub.1 -C.sub.4 -alkylsulfamoyl as substituents. Substituted phenylene then generally contains from 1 to 3, preferably 1 or 2, substituents.
R.sup.3, R.sup.4 and R.sup.5 are each for example methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, fluorine, chlorine or bromine.
Q is an alkali-detachable group. Such groups include for example chlorine, bromine, C.sub.l -C.sub.4 -alkylsulfonyl, phenylsulfonyl, OSO.sub.3 H, SSO.sub.3 H, OP(O) (OH).sub.2, C.sub.1 -C.sub.4 -alkylsulfonyloxy, substituted or unsubstituted phenylsulfonyloxy, C.sub.1 -C.sub.4 -alkanoyloxy, C.sub.1 -C.sub.4 -dialkylamino or a radical of the formula ##STR7## where L.sup.1, L.sup.2 and L.sup.3 are each independently of the others C.sub.1 -C.sub.4 -alkyl or benzyl and An.sup..THETA. is in each case one equivalent of an anion. Suitable anions include for example fluoride, chloride, bromide, iodide, mono-, di- or trichloroacetate, methanesulfonate, benzenesulfonate or 2- or 4-methylbenzenesulfonate.
Anchor radical E undergo substitutive or additive reactions with the hydroxyl or nitrogenous groups of the substrates to be treated.
The fact that the anchor radical reacts substitutively with the relevant groups in the substrates, for example with the hydroxyl groups of cellulose, means that the leaving groups or atoms (eg. fluorine or chlorine) in the anchor radical are replaced by the hydroxyl groups of
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Loffler Hermann
Patsch Manfred
Zamponi Andrea
BASF - Aktiengesellschaft
Powers Fiona T.
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