Kuhlthau, Hans-Peter; Beecken, Hermann;

Cationic dyestuffs

Cationic dyestuffs of the formula ##STR1## wherein R represents alkyl, alkenyl, cycloalkyl or aralkyl, R.sub.1 represents hydrogen, alkyl, alkenyl, cycloalkyl or aralkyl, R.sub.2 represents alkylene, Y represents oxygen or sulphur, R.sub.3 represents a direct bond or -CO-, A represents a carbocyclic six-membered ring or a heterocyclic ring, X.sup.- represents an anion and m represents the numbers 0 or 1, With the proviso that m can only be 1 if R.sub.3 denotes an alkylene group, are suitable for dyeing and printing of natural and synthetic materials.

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We claim:

1. Dyestuff of the formula: ##STR25## wherein R' represents C.sub.1 -C.sub.6 -alkyl, halo-C.sub.1 -C.sub.6 -alkyl, hydroxy-C.sub.1 -C.sub.6 -alkyl, cyano-C.sub.1 -C.sub.6 -alkyl, acetoxy-C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.4 -alkoxycarbonyl-C.sub.1 -C.sub.6 -alkyl, carbonyl-C.sub.1 -C.sub.6 -alkyl, aminocarbonyl-C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.7 -alkenyl, benzyl, phenylethyl, or ##STR26## wherein R.sub.17 denotes hydrogen or methyl and

R.sub.18 denotes methyl, ethyl, chloromethyl, methoxymethyl, ethoxymethyl, propoxymethyl, butoxymethyl, allyloxymethyl, phenoxymethyl, or phenyl;

R.sub.1 ' represents C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.7 -alkenyl, cyclopentyl, cyclohexyl, benzyl, .beta.-phenylethyl, C.sub.1 -C.sub.6 -alkylcyclopentyl, C.sub.1 -C.sub.6 -alkylcyclohexyl, C.sub.1 -C.sub.6 -alkylbenzyl, C.sub.1 -C.sub.6 -alkyl-.beta.-phenylethyl or C.sub.1 -C.sub.6 -alkyl substituted by halogen, hydroxyl, C.sub.1 -C.sub.4 -alkoxy, phenoxy, cyano, acetoxy, hydroxycarbonyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, C.sub.1 -C.sub.4 -alkoxycarbonyloxy, aminocarbonyl, C.sub.1 -C.sub.4 -alkylsulphonylamino, or C.sub.1 -C.sub.4 -alkylsulphonyl-C.sub.1 -C.sub.4 -alkylamino;

R.sub.2 represents ##STR27## R.sub.6 denotes hydrogen, methyl, ethyl, methoxymethyl, ethoxymethyl, propoxymethyl, butoxymethyl, allyloxymethyl, phenyl, or phenoxymethyl;

R.sub.7 denotes hydrogen, methyl, ethyl, butoxymethyl, methoxymethyl, ethoxymethyl, propoxymethyl, allyloxymethyl, phenyl, phenoxymethyl, or --Y--A';

R.sub.8 denotes hydrogen or methyl;

p denotes the numbers 1 - 6;

Y represents oxygen or sulphur;

R.sub.4 represents hydrogen, halogen, C.sub.1 -C.sub.6 -alkyl, halo-C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylcarbonylamino, C.sub.1 -C.sub.4 -alkylsulphonylamino, phenylcarbonylamino, phenylsulphonylamino, C.sub.1 -C.sub.4 -alkylcarbonyloxy, phenylcarbonyloxy, benzyloxy, .beta.-phenylethyloxy, or either of the last two mentioned radicals substituted in the phenyl ring by C.sub.1 -C.sub.6 -alkyl, cyano, phenyloxy, naphthyloxy, C.sub.1 -C.sub.6 -alkylphenyloxy, C.sub.1 -C.sub.6 -alkylnaphthyloxy, halophenyloxy, or halonaphthyloxy;

R.sub.4, in addition, when joined together with B represents a fused naphthalene ring or a fused tetralin ring;

R.sub.5 represents hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylcarbonylamino or C.sub.1 -C.sub.4 -alkylsulphonylamino, phenylcarbonylamino, phenylsulphonylamino, C.sub.1 -C.sub.4 -alkylcarbonyloxy, phenylcarbonyloxy, benzyloxy, .beta.-phenylethyloxy, or either of the last two mentioned radicals substituted in the phenyl ring by C.sub.1 -C.sub.6 -alkyl, phenyloxy, naphthyloxy, C.sub.1 -C.sub.6 -alkylphenyloxy, C.sub.1 -C.sub.6 -alkylnaphthyloxy, halophenoxy, or halonaphthyloxy;

R.sub.5, in addition, when joined together with B represent a fused naphthalene ring or a fused tetralin ring;

R.sub.13 ' represents hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.4 -alkoxy, cyclopentyl, cyclohexyl, benzyl, .beta.-phenylethyl, C.sub.1 -C.sub.6 -alkylcyclopentyl, C.sub.1 -C.sub.6 -alkylcyclohexyl, C.sub.1 -C.sub.6 -alkylbenzyl, C.sub.1 -C.sub.6 -alkyl-.beta.-phenylethyl, phenyloxy, naphthyloxy, C.sub.1 -C.sub.6 -alkylphenyloxy, C.sub.1 -C.sub.6 -alkylnaphthyloxy, halophenyloxy, halonapthyloxy, benzyloxy, .beta.-phenylethyl, C.sub.1 -C.sub.4 -alkylcarbonylamino, C.sub.1 -C.sub.4 -alkylsulphonylamino, phenylcarbonylamino, phenylsulphonylamino, a fused benzene ring, or a fused tetrahydrobenzene ring, either of which is fused in the 4,5-position or 5,6-position of D;

R.sub.14 represents C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.4 -alkoxy, phenoxy, benzyloxy, benzyl, trifluoromethyl, halogen, C.sub.1 -C.sub.4 -alkylcarbonylamino, C.sub.1 -C.sub.4 -alkylsulphonylamino, phenylcarbonylamino, phenylsulphonylamino, a fused benzene ring or a fused tetrahydrobenzene ring either of which is fused in the 6,7-position of D;

A' is a member of a group consisting of cyclohexyl, naphthyl, phenyl, or phenyl substituted by chloro, methyl, ethyl, isopropyl, sec. butyl, tert. butyl, tetramethylbutyl, nonyl, dodecyl, phenyl, benzyl, cyclohexyl, phenyl-isopropyl, methoxy, ethoxy, isopropoxy, phenylsulfonyl or methylthio;

n represents the numbers 0, 1, 2, or 3; and

X.sup.(-) represents an anion.

2. Dyestuff of the formula ##STR28## wherein R', R.sub.1 ', R.sub.4, R.sub.5, R.sub.6, R.sub.8, R.sub.13 ', R.sub.14, n, p, and X.sup.- have the same meaning as in claim 1;

R.sub.2 " represents ##STR29## R.sub.9 represents hydrogen, methyl, ethyl, methoxymethyl, ethoxymethyl, propoxymethyl, butoxymethyl, allyloxymethyl, phenyl, phenoxymethyl, or --O--(CH.sub.2).sub.q --(O).sub.m --A';

q represents the numbers 1-4;

m represents the numbers 0 or 1; and

A' represents phenyl or phenyl substituted by chloro or methyl.

3. Dyestuff according to claim 1, in which

R.sub.13 ' represents C.sub.1 -C.sub.4 -alkoxy and

R.sub.14 represents methyl, ethyl, methoxy, ethoxy, chlorine, bromine, fluorine, trifluoromethyl, phenoxy or benzyloxy.

4. Dyestuff according to claim 1 in which R.sub.13 ' represents methoxy or ethoxy,

R' represents methyl or ethyl,

R.sub.5 represents hydrogen,

R.sub.4 represents hydrogen, methoxy, chlorine or methyl,

p represents the number 2,

n represents the number 0,

y represents oxygen.

5. Dyestuff according to claim 2, in which

R.sub.13 ' represents C.sub.1 -C.sub.4 -alkoxy and

R.sub.14 represents methyl, ethyl, methoxy, ethoxy, chlorine, bromine, fluorine, trifluoromethyl, phenoxy or benzyloxy.

6. Dyestuff according to claim 2 in which

R.sub.13 ' represents methoxy or ethoxy,

R' represents methyl or ethyl,

R.sub.5 represents hydrogen,

R.sub.4 represents hydrogen, methoxy, chlorine or methyl,

q represents the numbers from 1-3,

n represents the number 0,

p represents the number 2,

m represents the number 0.

7. Dyestuff according to claim 2 in which

R.sub.13 ' represents methoxy or ethoxy,

R' represents methyl or ethyl,

R.sub.5 represents hydrogen,

R.sub.4 represents hydrogen, methoxy, chlorine or methyl,

q represents the number 2,

m represents the number 1.