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EP0033583A1 Expired / Lapsed EP ⏱️ 0.0 years remaining

Dyestuffs comprising two 5-membered heterocyclic nuclei fused to a central cyclohexadiene nucleus, processes for their preparation and their use for colouring synthetic textile materials

Assignee: Imperial Chemical Industries Ltd
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Filing: 1981-01-08
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Granted: —
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Expires: 2001-01-08
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Abstract

Abstract Dyestuffs of the general formula: wherein Z' and Z 2 are oxygen, sulphur or -NY' in which Y' is an optionally substituted hydrocarbon radical or an acyl radical; R 3 and R 4 each respresent a naphthyl radical or an optionally substituted phenyl radical; X 3 and X 4 each independently represent a hydrogen atom, chlorine, bromine, cyano, lower alkyl, lower alkoxy, optionally substituted aryl, optionally substituted carbamoyl, optionally substituted sulphamoyl, carboxylic acid or carboxylic acid ester group, provided that Z' and Z 2 may be the same or different when R 3 and R 4 are different, and Z' and Z 2 are different when R 3 and R 4 are the same. These dyestuffs are prepared by various processes and are useful in colouring synthetic textile materials.

Inventors

  • 👤 Colin William Greenhalgh
  • 👤 Nigel Hall
  • 👤 David Francis Newton

Bibliographic Details

Application Number —
Jurisdiction EP
Data Source google_patents
Last Synchronized 2026-11-07 22:38
CPC Classifications
C; C09; C09B; C09B57/00

Claims Analysis

Total Claims: 10
Claim 1
Independent Claim 213 words
Dyestuffs of the general formula (I): wherein Z 1 and Z 2 are oxygen, sulphur or Y 1 in which Y 1 is an optionally substituted hydrocarbon radical or an acyl radical; radical; R 3 and R 4 each represent a naphthyl radical, an unsubstituted phenyl radical or a phenyl radical substituted by at least one of the following:- nitro, halogen, lower alkyl, lower alkoxy, phenyl, hydroxy, lower alkoxyphenyl, phenoxy, cyano, carboxylic acid, carboxylic acid ester, optionally substituted carbamoyl, sulphonic acid, sulphonyl chloride, sulphonic acid ester, optionally substituted sulphamoyl, mercapto, lower alkylthio, phenylthio, primary, secondary, tertiary or quaternary amino, acylamino, phosphonic acid, phosphonic acid ester, lower alkylsulphonyl, phenylsulphonyl, aldehyde, azo, and acyloxy groups of the formula O.CO.T in which T 1 is an alkyl group containing at least two carbon atoms, a substituted phenyl group, a lower alkoxy group or a phenoxy group; X 3 and X each independently represent a hydrogen aton, chlorine, bromine, cyano, lower alkyl, lower alkoxy, optionally subotituted aryl, optionally substituted carbamcyl, optionally substituted sulphamoyl, carboxylic acid or carboxylic acid ester group, provided that Z 1 and Z 2 may be the same or different when R 3 and R 4 are different, and Z and Z 2 are different when R 3 and R 4 are the sane.
Claim 2
Dependent Claim 213 words
Dyestuffs of the general formula (I): wherein Z 1 and Z 2 are oxygen, sulphur or Y 1 in which Y 1 is an optionally substituted hydrocarbon radical or an acyl radical; radical; R 3 and R 4 each represent a naphthyl radical, an unsubstituted phenyl radical or a phenyl radical substituted by at least one of the following:- nitro, halogen, lower alkyl, lower alkoxy, phenyl, hydroxy, lower alkoxyphenyl, phenoxy, cyano, carboxylic acid, carboxylic acid ester, optionally substituted carbamoyl, sulphonic acid, sulphonyl chloride, sulphonic acid ester, optionally substituted sulphamoyl, mercapto, lower alkylthio, phenylthio, primary, secondary, tertiary or quaternary amino, acylamino, phosphonic acid, phosphonic acid ester, lower alkylsulphonyl, phenylsulphonyl, aldehyde, azo, and acyloxy groups of the formula O.CO.T in which T 1 is an alkyl group containing at least two carbon atoms, a substituted phenyl group, a lower alkoxy group or a phenoxy group; X 3 and X each independently represent a hydrogen aton, chlorine, bromine, cyano, lower alkyl, lower alkoxy, optionally subotituted aryl, optionally substituted carbamcyl, optionally substituted sulphamoyl, carboxylic acid or carboxylic acid ester group, provided that Z 1 and Z 2 may be the same or different when R 3 and R 4 are different, and Z and Z 2 are different when R 3 and R 4 are the sane.
Claim 3
Dependent Claim 27 words
Dyestuffs as claimed in claim 1 wherein the optionally substituted hydrocarbon radicals represented by Y 1 are optionally substituted lower alkyl radicals or optionally substitute phenyl radicals.
Claim 4
Dependent Claim 64 words
Dyestuffs as claimed in claim 1 or claim 2 wherein the.optionally substituted carbamoyl and sulphamoyl groups which may be present as substituents on the phenyl radicals represented by R 3 and R 4 , and which are represented by X 3 and X 4 , are of the formula: respectioly, in which L and L 2 are each independently hydrogen, lower alkyl or phenyl.
Claim 5
Dependent Claim 64 words
Dyestuffs as claimed in any one of claims 1 to 3 wherein the carboxylic acid ester groups which may be present as substituents on the phenyl radicals represented by R 3 and R 4 , and which are represented by X 3 and X 4 , are of the formula -COOL 3 wherein L 3 is an optionally substituted lower alkyl or phenyl radical.
Claim 6
Dependent Claim 108 words
A process for the preparation of the dyestuffs claimed in claim 1 which comprises reacting 1 mol proportion of a compound of formula (II): wherein X 3 , X 4 , Z 1 ' and Z 2 have the meanings defined in claim 1, with at least 2 mol proportions of a compound of formula (III): wherein B is hydrogen, lower alkyl or aryl, A is hydroxyl, 0-acyl or halogen, and R 3 has the meaning defined in claim 1, either as a melt or in a high-boiling inert solvent, to give the intermediate of formula (IV): which is subsequently oxidised to give the dyestuff of formula (I).
Claim 7
Dependent Claim 129 words
A process for the preparation of the dyestuffs claimed in claim 1 which comprises reacting substantially equimolar proportions of the compound of formula (II): wherein X 3 , X 4 , Z 1 and Z 2 have the meanings defined in claim 1, and the compound of formula (III): wherein A and B have the meanings defined in claim 5 and R 3 has the meaning defined in claim 1,to give the intermediate of formula (V): which is subsequently reacted with 1 mol proportion of the compound of formula (VI): wherein A and B have the meanings defined in claim 5 and R 4 has the meaning defined in claim 1, to give the intermediate of formula (VII): which is subsequently oxidised to give the dyestuff of formula (I).
Claim 8
Dependent Claim 161 words
A process for the preparation of the dyestuffs claimed in claim 1 wherein Z 1 and Z 2 are both oxygen which comprises reacting a quinone of formula (VIII): with a compound of the formula (IX): in which R 3 , X 3 and X 4 have the meanings defined in claim 1, B has the meaning defined in claim 5, X 5 and X 6 are hydrogen, chlorine or bromine, and Q is hydrogen, hydroxyl or 0-acyl, provided that when Q is hydrogen, at least X 3 and X 4 , or X 5 and X 6 must be chlorine or bromine, to give a compound of formula (X): which is then further reacted with a compound of formula (XI): wherein B and Q have the meanings defined above and R 4 has the meaning defined in claim 1, to give a compound of the formula (XII): which then cyclises with bond rearrangement to give a dyestuff of formula (I).
Claim 9
Dependent Claim 33 words
A process for colouring synthetic textile materials which comprises applying to the synthetic textile- material by a dyeing, padding or printing process an aqueous dispersion of a dyestuff as claimed in claim 1.
Claim 10
Dependent Claim 18 words
A process as claimed in claim 8 wherein the synthetic textile material is an arcmatic polyester textile material.

References Cited (Backward Citations)

FR2343785A1 Cited

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