Monoazo dyes which are free from water-solubilizing groups and which contain a fluorosulphonyl group and process for colouring polyamides and polyester materials therewith

A dispersion comprising a compound which is free from water solubilising groups of Formula (1):

• A--N.dbd.N--D Formula (1)
• wherein
• A and D each independently is an substituted or unsubstituted heterocyclic or carbocyclic group and
• at least one of A or D carries directly at least one --SO.sub.2 F group or carries a substituent to which at least one --SO.sub.2 F group is attached provided that when A.sup.1 --N.dbd.N-- is a p-fluorosulphonylphenylazo group, that at least one of the positions ortho or meta to the azo group is substituted, that when A.sup.1 --N.dbd.N-- is a m-fluorosulphonylphenylazo group, that at least 2 of the positions ortho or para to the azo group, or meta to both the fluorosulphonyl group are substituted, that when either A.sup.1 or D.sup.1 is a phenylene group substituted ortho to the azo group by an --SO.sub.2 F group, neither A.sup.1 or D.sup.1 are substituted at the position para to the azo group by an NO.sub.2 group, and also provided that one of A or D is not 3,5-difluorosulphonylthien-2-yl, 4-fluorosulphonylnaphth-1-yl, substituted or unsubstituted 1-phenyl-pyrazol-4-yl-5-one or ##STR49## or that one of A or D does not carry an --NCH.sub.2 CH(OH)CH.sub.2 Cl, --NCOCH.sub.2 Cl or --NCH.sub.3 CH.sub.2 SO.sub.2 F substituent and water.

A process for colouring polyamide and aromatic polyester textile material or fibre blends thereof which comprises applying to the synthetic textile material a compound, which is free from water solubilising groups, or a mixture of such compounds, of Formula (1):

• A--N.dbd.N--D Formula (1)
• wherein
• A and D each independently is a heterocyclic or carbocyclic group, which is unsubstituted or is substituted by one or more substituents selected from the group consisting of cyano, hydroxy, nitro, fluoro, chloro, bromo, iodo, fluorosulphonyl, trifluoromethyl, alkyl, alkoxy, aryl, aryloxy, fluorosulphonylaryl, fluorosulphonylaryloxy, --COalkyl, --COOalkyl,--OCOalkyl, --COaryl, --COOaryl, --OCOaryl, --NHCOalkyl, --NHCOaryl, --NHSO.sub.2 alkyl, --NHSO.sub.2 aryl, --Salkyl, --Saryl, --SO.sub.2 alkyl, --SO.sub.2 aryl, --SCN, --NR.sup.1 R.sup.2 in which R.sup.1 and R.sup.2 each independently is --H, alkyl, aryl or cycloalkyl, and groups of Formula R.sup.19 N--Y--X--W in which Y is a direct link or C.dbd.O, X is a direct link, alkyl, alkenyl, aryl, heterocyclic, alkylOalkyl, alkylNHalkyl or --NR.sup.20 --Z-- or --O--Z-- in which Z is alkyl, alkenyl, aryl, heterocyclic, alkylOalkyl, alkylNHalkyl or a direct link and R.sup.20 is --H, alkyl, aryl or alkylaryl, W is --CO.sub.2 R.sup.21, --OCOR.sup.21, --OH or --CN in which R.sup.21 is alkyl, aryl, alkylaryl, alkylOalkyl or alkylOH, and R.sup.19 is --H or substituted or unsubstituted alkyl, each of the alkyl, alkoxy, aryl, aryloxy parts of the above substituents for A, D, R.sup.1 and R.sup.2 being unsubstituted or substituted by one or more of --OH, --CN, --F, --Cl, --Br, --I, --SO.sub.2 F, alkoxy, alkenyl, phenyl, phenylSO.sub.2 F, aryloxy, aryloxySO.sub.2 F, --N(alkyl).sub.2, --OCOalkyl, --OCOalkylCl, --COOalkyl, --COOalkylOH, --COOalkylCN, --COOalkylCOalkyl, --COOalkylphenyl, --OCOphenyl, --COphenylSO.sub.2 F, --OCOphenylNO.sub.2, --OCOphenylalkyl, --OCOphenylalkoxy, --COOphenyl, --OCO(fluorosulphonylphenyl), --OalkylCN, --COOalkyCOalkyl, --COOalkyCOphenyl, --OCOalkylOphenyl, --COOalkylOalkylOalkyl, --OCOalkylCOOalkyl, --OalkylCOOalkyl, --OalkylCOOalkylOalkyl, --OalkylCOOalkylCOOalkyl, --OalkylOCOalkyCOalkyl, --COOalkylOCOalkyl or --COOalkylCOOalkyl, ##STR50## in which L is --H or alkyl, and at least one of A or D is substituted by at least one --SO.sub.2 F group or is substituted by at least one substituent which is itself substituted by at least one --SO.sub.2 F group, except for 4-(4-fluorosulphonylphenylazo)-N,N-dimethylaniline, provided that one of A or D is not 3,5-difluorosulphonylthien-2-yl, substituted or unsubstituted 1-phenyl-pyrazol-4-yl-5-one, 4-fluorosulphonylnaphth-1-yl or ##STR51## or that one of A or D does not carry an --NCH.sub.2 CH(OH)CH.sub.2 Cl, --NCOCH.sub.2 Cl or --NCH.sub.2 CH.sub.2 SO.sub.2 F substituent.

A process for colouring a synthetic textile material or fibre blend thereof which comprises applying to the synthetic textile material a compound, which is free from water solubilising groups, or a mixture of such compounds, of Formula (1):

• A--N.dbd.N--D FORMULA (1)
• wherein
• A and D each independently is a heterocyclic or carbocyclic group, which is unsubstituted or is substituted by one or more substituents selected from the group consisting of cyano, hydroxy, nitro, fluoro, chloro, bromo, iodo, fluorosulphonyl, trifluoromethyl, alkyl, alkoxy, aryl, aryloxy, fluorosulphonylaryl, fluorosulphonylaryloxy, --COalkyl, --COOalkyl, --OCOalkyl, --COaryl, --COOaryl, --OCOaryl, --NHCOalkyl, --NHCOaryl, --NHSO.sub.2 alkyl, --NHSO.sub.2 aryl, --Salkyl, --Saryl, --SO.sub.2 alkyl, --SO.sub.2 aryl, --SCN, --NR.sup.1 R.sup.2 in which R.sup.1 and R.sup.2 each independently is --H, alkyl, aryl or cycloalkyl, and groups of Formula R.sup.19 --N--Y--X--W in which Y is a direct link or C.dbd.O, X is a direct link, alkyl, alkenyl, aryl, heterocyclic, alkyCOalkyl, alkylNHalkyl or --NR.sup.20 --Z-- or --O--Z-- in which Z is alkyl, alkenyl, aryl, heterocyclic, alkylOalkyl, alkylNHalkyl or a direct link and R.sup.20 is --H, alkyl, aryl or alkylaryl, W is --CO.sub.2 R.sup.21, --OCOR.sup.21, --OH or --CN in which R.sup.21 is alkyl, aryl, alkylaryl, alkylOalkyl or alkylOH, and R.sup.19 is --H or substituted or unsubstituted alkyl, each of the alkyl, alkoxy, aryl, aryloxy parts of the above substituents for A, D, R.sup.1 and R.sup.2 being unsubstituted or substituted by one or more of --OH, --CN, --F, --Cl, --Br, --I, --SO.sub.2 F, alkoxy, alkenyl, phenyl, phenylSO.sub.2 F, aryloxy, aryloxySO.sub.2 F, --N(alkyl).sub.2, --OCOalkyl, --OCOalkylCl, --COOalkyl, --COOalkylOH, --COOalkylCN, --COOalkylCOalkyl, --COOalkylphenyl, --OCOphenyl, --COphenylSO.sub.2 F, --OCOphenylNO.sub.2, --OCOphenylalkyl, --OCOphenylalkoxy, --COOphenyl, --OCO(fluorosulphonylphenyl), --OalkylCN, --COOalkylOalkyl, --COOalkylOphenyl, --OCOalkylOphenyl, --COOalkylOalkylOalkyl, --OCOalkylCOOalkyl, --OalkylCOOalkyl, --OalkylCOOalkylOalkyl, --OalkylCOOalkylCOOalkyl, --OalkylOCOalkylOalkyl, --COOalkylOCOalkyl or --COOalkylCOOalkyl, ##STR52## in which L is --H or alkyl, at least one of A or D being substituted by at least one --SO.sub.2 F group or is substituted by at least one substituent which is itself substituted by at least one --SO.sub.2 F group, and
• at least one of A or D is substituted by at least one ester group or is substituted by at least one substituent which is itself substituted by at least one ester group, provided that one of A or D is not ##STR53##

A process for colouring a polyester textile material or fibre blend thereof which comprises applying to the polyester textile material a compound or mixture thereof, which is free from water solubilising groups, of Formula (1):

• A--N.dbd.N--D FORMULA (1)
• wherein
• A and D each independently is a heterocyclic or carbocyclic group, which is unsubstituted or is substituted by one or more substituents selected from the group consisting of cyano, hydroxy, nitro, fluoro, chloro, bromo, iodo, fluorosulphonyl, trifluoromethyl, alkyl, alkoxy, aryl, aryloxy, fluorosulphonylaryl, fluorosulphonylaryloxy, --COalkyl, --COOalkyl,--OCOalkyl, --COaryl, --COOaryl, --OCOaryl, --NHCOalkyl, --NHCOaryl, --NHSO.sub.2 alkyl, --NHSO.sub.2 aryl, --Salkyl, --Saryl, --SO.sub.2 alkyl, --SO.sub.2 aryl, --SCN, --NR.sup.1 R.sup.2 in which R.sup.1 and R.sup.2 each independently is --H, alkyl, aryl or cycloalkyl, and groups of Formula R.sup.19 --N--Y--X--W in which Y is a direct link or C.dbd.O, X is a direct link, alkyl, alkenyl, aryl, heterocyclic, alkylOalkyl, alkylNHalkyl or --NR.sup.20 --Z-- or --O--Z-- in which Z is alkyl, alkenyl, aryl, heterocyclic, alkylOalkyl, alkylNHalkyl or a direct link and R.sup.20 is --H, alkyl, aryl or alkylaryl, W is --CO.sub.2 R.sup.21, --OCO R.sup.21, --OH or --CN in which R.sup.21 is alkyl, aryl, alkylaryl, alkylOalkyl or alkylOH, and R.sup.19 is --H or substituted or unsubstituted alkyl, each of the alkyl, alkoxy, aryl, aryloxy parts of the above substituents for A, D, R.sup.1 and R.sup.2 being unsubstituted or substituted by one or more of --OH, --CN, --F, --Cl, --Br, --I, --SO.sub.2 F, alkoxy, alkenyl, phenyl, phenylSO.sub.2 F, aryloxy, aryloxySO.sub.2 F, --N(alkyl).sub.2, --OCOalkyl, --OCOalkylCl, --COOalkyl, --COOalkylOH, --COOalkylCN, --COOalkylCOalkyl, --COOalkylphenyl, --OCOphenyl, --COphenylSO.sub.2 F, --OCOphenylNO.sub.2, --OCOphenylalkyl, --OCOphenylalkoxy, --COOphenyl, --OCO(fluorosulphonylphenyl), --OalkylCN, --COOalkylOalkyl, --COOalkylOphenyl, --OCOalkylOphenyl, --COOalkylOalkylOalkyl, --OCOalkylCOOalkyl, --OalkylCOOalkyl, --OalkylCOOalkylOalkyl, --OalkylCOOalkylCOOalkyl, --OalkylOCOalkylOalkyl, --COOalkylOCOalkyl or --COOalkylCOOalkyl, ##STR54## in which L is --H or alkyl, except for 4-(4-fluorosulphonylphenylazo)-N,N-dimethylaniline, provided that one of A or D is not 3,5-difluorosulphonylthien-2-yl, substituted or unsubstituted 1-phenylpyrazol-4-yl-5one, 4-fluorosulphonylnaphth-1-yl or 4-nitro-2-fluorosulphonylphenyl or that one of A or D does not carry an --NCH.sub.2 CH.sub.2 SO.sub.2 F substitutent.

A compound, which is free from water solubilising groups, of Formula (2):

• A.sup.1 --N.dbd.N--D.sup.1 Formula ( 2)
• in which
• A.sup.1 --N.dbd.N-- is a substituted or unsubstituted heterocyclic or carbocyclic azo group and D.sup.1 is a coupler, each of A.sup.1 and D.sup.1 independently being selected from thienyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, pyridyl, 1,2,4- and 1,3,4-thiadiazolyl, furanyl, pyrrolyl, pyridazyl, pyridonyl, pyrimidyl, pyrazinyl, benzothiazolyl, benzoisothiazolyl, quinolinyl, isoquinolinyl, indolyl, pyridothiazolyl, pyridoisothiazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, phenyl and naphthyl, and at least one of A.sup.1 or D.sup.1 carries directly at least one --SO.sub.2 F group or carries a substituent to which at least one --SO.sub.2 F group is attached, provided that when A.sup.1 --N.dbd.N-- is a p-fluorosulphonylphenylazo group, that at least one of the positions ortho or meta to the azo group is substituted, that when A.sup.1 --N.dbd.N-- is a m-fluorosulphonylphenylazo group, that at least 2 of the positions ortho or para to the azo group, or meta to both the fluorosulphonyl group are substituted, that when either A.sup.1 or D.sup.1 is a phenylene group substituted ortho to the azo group by an --SO.sub.2 F group, neither A.sup.1 or D.sup.1 are substituted at the position para to the azo group by an NO.sub.2 group, the substituents for A.sup.1 and D.sup.1 being selected from the group consisting of cyano, hydroxy, nitro, fluoro, chloro, bromo, iodo, fluorosulphonyl, trifluoromethyl, alkyl, alkoxy, aryl, aryloxy, fluorosulphonylaryl, fluorosulphonylaryloxy, --COalkyl, --COOalkyl, --OCOalkyl, --COaryl, --COOaryl, --OCOaryl, --NHCOalkyl, --NHSO.sub.2 alkyl, --NHSO.sub.2 aryl, --Salkyl, --Saryl, --SO.sub.2 alkyl, --SO.sub.2 aryl, --SCN, --NR.sup.1 R.sup.2 in which R.sup.1 and R.sup.2 each independently is --H, alkyl, aryl or cycloalkyl, and groups of Formula R.sup.19 --N--Y--X--W in which Y is a direct link or C.dbd.O, X is a direct link, alkyl, alkenyl, aryl, heterocyclic, alkylOalkyl, alkylNHalkyl or --NR.sup.20 --Z-- or --O--Z-- in which Z is alkyl, alkenyl, aryl, heterocyclic, alkylOalkyl, alkylNHalkyl or a direct link and R.sup.20 is --H, alkyl, aryl or alkylaryl, W is --CO.sub.2 R.sup.21, --OCOR.sup.21, --OH or --CN in which R.sup.21 is alkyl, aryl, alkylaryl, alkylOalkyl or alkylOH, and R.sup.19 is --H or substituted or unsubstituted alkyl, each of the alkyl, alkoxy, aryl, aryloxy parts of the above substituents for A, D, R.sup.1 and R.sup.2 being unsubstituted or substituted by one or more of --OH, --CN, --F, --Cl, --Br, --I, --SO.sub.2 F, alkoxy, alkenyl, phenyl, phenylSO.sub.2 F, aryloxy, aryloxySO.sub.2 F, --N(alkyl).sub.2 --OCOalkyl, --OCOalkylCl, --COOalkyl, --COOalkylOH, --COOalkylCN, --COOalkylCOalkyl, --COOalkylphenyl, --OCOphenyl, --COphenylSO.sub.2 F, --OCOphenylNO.sub.2, --OCOphenylalkyl, --OCOphenylalkoxy, --COOphenyl, --OCO(fluorosulphonylphenyl), --OalkylCN, --COOalkylOalkyl, --COOalkylOphenyl, --OCOalkylOphenyl, --COOalkylOalkylOalkyl, --OCOalkylCOOalkyl, --OalkylCOOalkyl, --OalkylCOOalkylOalkyl, --OalkylCOOalkylCOOalkyl, --OalkylOCOalkylOalkyl, --COOalkylOCOalkyl or --COOalkylCOOalkyl, ##STR59## in which L is --H or alkyl, provided that A.sup.1 is not 3,5-difluorosulphonylthien-2-yl, that one of A.sup.1 or D.sup.1 is not 4-fluorosulphonylnaphth-1-yl or substituted 4-hydroxynaphth-1-yl, that one of A.sup.1 or D.sup.1 does not carry a --NCH.sub.2 CH.sub.2 SO.sub.2 F substituent.