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US 4,244,691 AGranted
Novel water-soluble anthraquinone dyes
AssigneeCiba-Geigy Corporation
InventorJean-Marie Adam
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AssigneeCiba-Geigy Corporation
InventorJean-Marie Adam
Estimating the term…
The invention relates to novel, water-soluble anthraquinone dyes which, in the form of the free acid, have the formula I ##STR1## in which X is halogen, R.sub.1 is an unbranched or branched alkyl radical having 4 to 8 carbon atoms, R.sub.2 and R.sub.3 independently of one another are an unbranched or branched alkyl radical having 1 to 4 carbon atoms, R.sub.4 is hydrogen, an unbranched or branched alkyl radical having 1 to 4 carbon atoms, a free or acylated amino group or a fibre-reactive radical bonded via an amino group, R.sub.5 is hydrogen or an unbranched or branched alkyl radical having 1 to 4 carbon atoms and R.sub.6 and R.sub.7 independently of one another are hydrogen, an unbranched or branched alkyl radical having 1-4 carbon atoms, a --SO.sub.3 H group, halogen or a radical of the formula --CH.sub.2 --NH--CO--Y, in which Y is an alkyl or alkenyl radical having 1 to 4 carbon atoms which is unsubstituted or substituted by one or two halogen atoms, or is a substituted or unsubstituted phenyl radical, with the proviso that at least one of the radicals R.sub.6 or R.sub.7 is a --SO.sub.3 H group.
A novel water-soluble anthraquinone dye, or a mixture of such dyes, which, in the form of the free acid, has or have the formula I ##STR39## in which X is halogen, R.sub.1 is an unbranched or branched alkyl radical having 4 to 8 carbon atoms, R.sub.2 and R.sub.3 independently of one another are an unbranched or branched alkyl radical having 1 to 4 carbon atoms, R.sub.4 is hydrogen, an unbranched or branched alkyl radical having 1 to 4 carbon atoms, a free or acylated amino group or a fibre-reactive radical bonded via an amino group, R.sub.5 is hydrogen or an unbranched or branched alkyl radical having 1 to 4 carbon atoms and R.sub.6 and R.sub.7 independently of one another are hydrogen, an unbranched or branched alkyl radical having 1-4 carbon atoms, a --SO.sub.3 H group, halogen or a radical of the formula --CH.sub.2 --NH--CO--Y, in which Y is an alkyl or alkenyl radical having 1 to 4 carbon atoms which is unsubstituted or substituted by one or two halogen atoms, or is a substituted or unsubstituted phenyl radical, with the proviso that at least one of the radicals R.sub.6 or R.sub.7 is a --SO.sub.3 H group.
A process for the preparation of a novel, water-soluble anthraquinone dye which, in the form of the free acid, has the formula II ##STR42## in which X is halogen, R.sub.1 is an unbranched or branched alkyl radical having 4 to 8 carbon atoms, R.sub.2 and R.sub.3 independently of one another are an unbranched or branched alkyl radical having 1 to 4 carbon atoms, R.sub.4 is hydrogen, an unbranched or branched alkyl radical having 1 to 4 carbon atoms, a free or acylated amino group or a fibre-reactive radical bonded via an amino group, R.sub.5 is hydrogen or an unbranched or branched alkyl radical having 1 to 4 carbon atoms and R.sub.7 ' is hydrogen, an unbranched or branched alkyl radical having 1 to 4 carbon atoms, halogen or a radical of the formula --CH.sub.2 --NH--CO--Y, in which Y is an alkyl or alkenyl radical having 1-4 carbon atoms, which is unsubstituted or substituted by one or two halogen atoms, or is a substituted or unsubstituted phenyl radical, which comprises selectively monosulfonating an anthraquinone compound of the formula V ##STR43## in which X, R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are as defined above, and, if desired, subsequently halogenating the reaction product in the phenol ring or reacting it with a compound of the formula HOCH.sub.2 --NH--CO--Y, in which Y is as defined above.
A process for the preparation of a novel, water-soluble anthraquinone dye which, in the form of the free acid, has the formula III ##STR46## in which X is halogen, R.sub.1 is an unbranched or branched alkyl radical having 4 to 8 carbon atoms, R.sub.2 and R.sub.3 independently of one another are an unbranched or branched alkyl radical having 1 to 4 carbon atoms, R.sub.4 is hydrogen, an unbranched or branched alkyl radical having 1 to 4 carbon atoms, a free or acylated amino group or a fibre-reactive radical bonded via an amino group, R.sub.5 is hydrogen or an unbranched or branched alkyl radical having 1 to 4 carbon atoms and R.sub.6 ' is hydrogen, an unbranched or branched alkyl radical having 1 to 4 carbon atoms, halogen or a radical of the formula --CH.sub.2 --NH--CO--Y, in which Y is an alkyl or alkenyl radical having 1-4 carbon atoms, which is unsubstituted or substituted by one or two halogen atoms, or is a substituted or unsubstituted phenyl radical, which comprises effecting selective desulfonation in the aniline ring of an anthraquinone compound of the formula IV ##STR47## in which X, R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are as defined above, and, if desired, subsequently replacing a hydrogen atom in the aniline ring of the resulting product by halogen or a group of the formula --CH.sub.2 --NH--CO--Y, in which Y is as defined above.
A process for the preparation of a novel, water-soluble anthraquinone dye which, in the form of the free acid, has the formula IV ##STR48## in which X is halogen, R.sub.1 is an unbranched or branched alkyl radical having 4 to 8 carbon atoms, R.sub.2 and R.sub.3 independently of one another are an unbranched or branched alkyl radical having 1 to 4 to carbon atoms, R.sub.4 is hydrogen, an unbranched or branched alkyl radical having 1 to 4 carbon atoms, a free or acylated amino group or a fibre-reactive radical bonded via an amino group and R.sub.5 is hydrogen or an unbranched or branched alkyl radical having 1 to 4 carbon atoms, which comprises sulfonating an anthraquinone compound of the formula V ##STR49## in which X, R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are as defined above, so that two sulfonic acid groups are introduced.
An intermediate of the formula VI ##STR50## in which X is halogen, R.sub.2 and R.sub.3 independently of one another are an unbranched or branched alkyl radical having 1 to 4 carbon atoms, R.sub.4 is hydrogen, an unbranched or branched alkyl radical having 1 to 4 carbon atoms, a free or acylated amino group or a fibre-reactive radical bonded via an amino group, R.sub.5 is hydrogen or an unbranched or branched alkyl radical having 1 to 4 carbon atoms and W is halogen or a --SO.sub.3 H group.
An intermediate of the formula V ##STR51## in which X is halogen, R.sub.1 is an unbranched or branched alkyl radical having 4 to 8 carbon atoms, R.sub.2 and R.sub.3 independently of one another are an unbranched or branched alkyl radical having 1 to 4 carbon atoms, R.sub.4 is hydrogen, an unbranched or branched alkyl radical having 1 to 4 carbon atoms, a free or acylated amino group or a fibre-reactive radical bonded via an amino group and R.sub.5 is hydrogen or an unbranched or branched alkyl radical having 1 to 4 carbon atoms.
An intermediate of the formula IX ##STR55## in which X, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are as defined above and W' is halogen.
Dependencies are inferred from the claim text.