US 5,453,501 AGranted

Phthalocyanine reactive dyestuffs

AssigneeBayer Aktiengesellschaft

InventorHorst Jager

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Abstract

Phthalocyanine reactive dyestuffs which, in the form of the free acid, have the formula (1) ##STR1## in which the variable radicals have the meaning given in the description, are prepared by condensation of the corresponding amines with cyanuric fluoride or cyanuric chloride in any desired order. The reactive dyestuffs according to the invention exhibit good wet and light fastness properties and are used for the dyeing and printing of cotton.

Claims10

Dependent claims

A phthalocyanine reactive dyestuff which, in the form of the free acid, has the formula ##STR37## in which Pc denotes a metal-free or metal containing phthalocyanine,

R.sup.1 and R.sup.2 independently of one another, represent hydrogen, or C.sub.1 -C.sub.6 -alkyl unsubstituted or substituted by OCH.sub.3, OH, COOH, SO.sub.3 H or phenyl,
B denotes a radical selected from the group consisting of ##STR38## an araliphatic radical of the formula ##STR39## an aromatic radical selected from the group consisting of ##STR40## wherein the phenylene or naphthylene rings are unsubstituted or substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, halogen or acid groups,
X represents chlorine or fluorine,
Y represents SO.sub.2 CH.dbd.CH.sub.2, SO.sub.2 CH.sub.2 CH.sub.2 OSO.sub.3 H, SO.sub.2 CH.sub.2 CH.sub.2 Cl, SO.sub.2 CH.sub.2 CH.sub.2 S.sub.2 O.sub.3 H, SO.sub.2 CH.sub.2 CH.sub.2 OPO.sub.3 H.sub.2, or SO.sub.2 CH.sub.2 CH.sub.2 OOCCH.sub.3,
R.sup.5 represents hydrogen, C.sub.1 -C.sub.6 -alkyl which is optionally interrupted by O, S, SO.sub.2, NR.sup.7 CO or NR.sup.7, NR.sup.7 SO.sub.2, a 5 or 6 membered cycloaliphatic radical, or a radical of the formula ##STR41## in which k is 1 to 4 and the ring D is unsubstituted or is substituted by Cl, NO.sub.2, COOH, SO.sub.3 H, CH.sub.3, OCH.sub.3, SO.sub.2 CH.sub.2 CH.sub.2 OSO.sub.3 H, SO.sub.2 CH.dbd.CH.sub.2 or CH.sub.2 SO.sub.2 CH.sub.2 CH.sub.2 OSO.sub.3 H,
R.sup.6 has the meaning given for R.sup.5 or represents a phenyl or naphthyl radical which is optionally substituted by OCH.sub.3, OC.sub.2 H.sub.5, OCH.sub.2 CH.sub.2 OH, CH.sub.3, C.sub.2 H.sub.5, --CH(CH.sub.3).sub.2, F, Cl, Br, COOH, SO.sub.3 H, NO.sub.2, SO.sub.2 CH.sub.2 CH.sub.2 OSO.sub.3 H, CH.sub.2 SO.sub.2 CH.sub.2 CH.sub.2 OSO.sub.3 H, CH.sub.2 SO.sub.2 CH.dbd.CH.sub.2 or SO.sub.2 CH.dbd.CH.sub.2, or the radicals R.sup.5 and R.sup.6, together with the nitrogen atom, form a ring optionally containing as an additional ring hetero moiety O, NH, NCH.sub.3, NCOCH.sub.3, N--C.sub.2 H.sub.4 SO.sub.2 CH.sub.2 .dbd.CH, S, SO or SO.sub.2,
R.sup.7 represents hydrogen or C.sub.1 -C.sub.4 -alkyl;
which is optionally substituted by OH, Cl, F, COOH, SO.sub.3 H, CH.sub.2, OSO.sub.3 H, SO.sub.2 CH.dbd.CH.sub.2, CN, OCH.sub.3, SO.sub.2 CH.sub.2 CH.sub.2 Cl or SO.sub.2 CH.sub.2 CH.sub.2 OSO.sub.3 H,
a is 0 to 3,
b is 0 to 3,
c is 1 to 3,
a+b+c being at most 4, and
R.sup.8 and R.sup.9 independently of one another, represent hydrogen or C.sub.1 -C.sub.6 -alkyl which is unsubstituted or substituted by OCH.sub.3, OH, COOH, SO.sub.3 H or phenyl.

10 more elements

Dependencies are inferred from the claim text.

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Abstract

A phthalocyanine reactive dyestuff which, in the form of the free acid, has the formula ##STR37## in which Pc denotes a metal-free or metal containing phthalocyanine,

R.sup.1 and R.sup.2 independently of one another, represent hydrogen, or C.sub.1 -C.sub.6 -alkyl unsubstituted or substituted by OCH.sub.3, OH, COOH, SO.sub.3 H or phenyl,
B denotes a radical selected from the group consisting of ##STR38## an araliphatic radical of the formula ##STR39## an aromatic radical selected from the group consisting of ##STR40## wherein the phenylene or naphthylene rings are unsubstituted or substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, halogen or acid groups,
X represents chlorine or fluorine,
Y represents SO.sub.2 CH.dbd.CH.sub.2, SO.sub.2 CH.sub.2 CH.sub.2 OSO.sub.3 H, SO.sub.2 CH.sub.2 CH.sub.2 Cl, SO.sub.2 CH.sub.2 CH.sub.2 S.sub.2 O.sub.3 H, SO.sub.2 CH.sub.2 CH.sub.2 OPO.sub.3 H.sub.2, or SO.sub.2 CH.sub.2 CH.sub.2 OOCCH.sub.3,
R.sup.5 represents hydrogen, C.sub.1 -C.sub.6 -alkyl which is optionally interrupted by O, S, SO.sub.2, NR.sup.7 CO or NR.sup.7, NR.sup.7 SO.sub.2, a 5 or 6 membered cycloaliphatic radical, or a radical of the formula ##STR41## in which k is 1 to 4 and the ring D is unsubstituted or is substituted by Cl, NO.sub.2, COOH, SO.sub.3 H, CH.sub.3, OCH.sub.3, SO.sub.2 CH.sub.2 CH.sub.2 OSO.sub.3 H, SO.sub.2 CH.dbd.CH.sub.2 or CH.sub.2 SO.sub.2 CH.sub.2 CH.sub.2 OSO.sub.3 H,
R.sup.6 has the meaning given for R.sup.5 or represents a phenyl or naphthyl radical which is optionally substituted by OCH.sub.3, OC.sub.2 H.sub.5, OCH.sub.2 CH.sub.2 OH, CH.sub.3, C.sub.2 H.sub.5, --CH(CH.sub.3).sub.2, F, Cl, Br, COOH, SO.sub.3 H, NO.sub.2, SO.sub.2 CH.sub.2 CH.sub.2 OSO.sub.3 H, CH.sub.2 SO.sub.2 CH.sub.2 CH.sub.2 OSO.sub.3 H, CH.sub.2 SO.sub.2 CH.dbd.CH.sub.2 or SO.sub.2 CH.dbd.CH.sub.2, or the radicals R.sup.5 and R.sup.6, together with the nitrogen atom, form a ring optionally containing as an additional ring hetero moiety O, NH, NCH.sub.3, NCOCH.sub.3, N--C.sub.2 H.sub.4 SO.sub.2 CH.sub.2 .dbd.CH, S, SO or SO.sub.2,
R.sup.7 represents hydrogen or C.sub.1 -C.sub.4 -alkyl;
which is optionally substituted by OH, Cl, F, COOH, SO.sub.3 H, CH.sub.2, OSO.sub.3 H, SO.sub.2 CH.dbd.CH.sub.2, CN, OCH.sub.3, SO.sub.2 CH.sub.2 CH.sub.2 Cl or SO.sub.2 CH.sub.2 CH.sub.2 OSO.sub.3 H,
a is 0 to 3,
b is 0 to 3,
c is 1 to 3,
a+b+c being at most 4, and
R.sup.8 and R.sup.9 independently of one another, represent hydrogen or C.sub.1 -C.sub.6 -alkyl which is unsubstituted or substituted by OCH.sub.3, OH, COOH, SO.sub.3 H or phenyl.

10 more elements