Reactive aluminum phthalocyanine dyestuffs, processes for their preparation and their use
AssigneeDyStar Textilfarben GmbH & Co. Deutschland KG
InventorsKarl-Josef Herd, Klaus Saitmacher
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Abstract
Novel aluminum phthalocyanine reactive dyestuffs of the formula (1) ##STR1## in which x is Cl or OH; Z is vinyl or a group of the formula --CH.sub.2 CH.sub.2 --Y, in which Y is a substituent which can be eliminated under alkaline conditions, c is a number from 0.5 to 4; M is a hydrogen, an alkali metal or a substituted or unsubstituted ammonium ion; and R.sup.1 and R.sup.2 independently of one another are hydrogen, substituted or unsubstituted C.sub.1 -C.sub.6 alkyl, a C.sub.1 -C.sub.6 -alkyl which is substituted by one or two radicals of the formulae OH, SO.sub.3 M or OSO.sub.3 M, a substituted or unsubstituted phenyl or a radical of the formulae (2), (3) or (4) ##STR2##
Claims14
An aluminum phthalocyanine of the formula (1) ##STR27## in which X is Cl or OH;
- Z is vinyl or a group of the formula --CH.sub.2 CH.sub.2 --Y, in which Y is a substituent which can be eliminated under alkaline conditions;
- a is a number from 0 to 3;
- b is a number from 0 to 4;
- c is a number from 0.5 to 4;
- M is hydrogen, an alkali metal or a substituted or unsubstituted ammonium ion;
- and
- R.sup.1 and R.sup.2 independently of one another are hydrogen, C.sub.1 -C.sub.6 -alkyl, a C.sub.1 -C.sub.6 -alkyl which is substituted by one or two radicals of the formulae OH, SO.sub.3 M or OSO.sub.3 M, phenyl, a phenyl which is substituted by one to three radicals of the fomulae OH, SO.sub.3 M or COOM or a radical of the formulae (2), (3) or (4) ##STR28## in which n is a number from 0 to 3,
- m is the number 0 or 1,
- where the sum n+m is 1, 2, 3 or 4,
- x is an integer from 2 to 6,
- y is a number from 0 to 3,
- W is C.sub.1 -C.sub.6 -alkylene, --(CH.sub.2).sub.2 --O--(CH.sub.2).sub.2 -- or a chemical bond and
- Y.sup.1 is --CH.dbd.CH.sub.2, --CH.sub.2 CH.sub.2 Cl, --CH.sub.2 CH.sub.2 OH or --CH.sub.2 CH.sub.2 OSO.sub.3 M;
- or R.sup.1 and R.sup.2, together with the adjacent nitrogen atom, form a 5 to 7-membered saturated or unsaturated N-heterocyclic radical, or, with a further hetero group selected from the group consisting of --O--, --S--, --SO.sub.2 --, --N.dbd. and .dbd.NR.sup.3, in which R.sup.3 is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -hydroxyalkyl, C.sub.1 -C.sub.4 -hydroxyalkyl, C.sub.1 -C.sub.4 -chloroalkyl or C.sub.1 -C.sub.4 -sulfatoalkyl, form a 5- to 8-membered saturated or unsaturated heterocyclic radical.
A process for the preparation of a compound of the formula (1b) ##STR41## in which a is a number from 0 to 3.0;
- c is a number from 0.5 to 4.0;
- d is a number from 0.5 to 2.0;
- x is a number from 2 to 6;
- Z.sup.2 is vinyl or .beta.-sulfatoethyl and
- M is hydrogen, an alkali metal or a substituted or unsubstituted ammonium ion, which comprises reacting a compound of the formula (7a) ##STR42## with a stoichiometric amount, corresponding to the desired number d, of an alkylaminosulfonic acid of the formula H.sub.2 N--(CH.sub.2).sub.x --SO.sub.3 M under alkaline conditions to give a compound of the formula (8), ##STR43## the SO.sub.2 Cl groups corresponding to the number c being hydrolyzed, reacting the compound of the formula (8) with chlorosulfonic acid and thionyl chloride, the sulfo groups of the sulfonamidoalkyl radical and some of the sulfo groups bonded directly to the phthalocyanine chromophore being converted into SO.sub.2 Cl groups;
- reducing the resulting reaction product with a reducing agent, sulfinic acid groups being formed from the SO.sub.2 Cl groups;
- ethoxylating the resulting reaction product, the sulfinic acid radicals being converted into hydroxyethylsulfonyl radicals;
- and subsequently sulfating the product, a compound of the formula (1 b) where Z.sup.2 is (.beta.-sulfatoethyl being formed, which, optionally, is subjected to an elimination reaction to give a compound of the formula (1b) where Z.sup.2 is vinyl.
Dependencies are inferred from the claim text.