US 4,051,084 A · Cationic dyestuffs

Abstract

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.

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.

15 more elements

Description6,123 words

Summary3,609 words

#The invention relates to new cationic dyestuffs of the general formula ##STR2## wherein R represents an alkyl, alkenyl, cycloalkyl or aralkyl radical,

#R.sub.1 represents hydrogen or an alkyl, alkenyl, cycloalkyl or aralkyl radical,

#R.sub.2 represents an alkylene group,

Detailed description2,514 words

#18 g of 2-amino-6-methoxybenzthiazole are dissolved in a mixture of 120 ml of glacial acetic acid and 60 ml of water. 29 ml of 48% strength sulphuric acid are then added and the amount of nitrosylsulphuric acid corresponding to 7 g of sodium nitrite is then added dropwise at -5.degree. C. After stirring for a further hour at this temperature, 1 g of amidosulphonic acid is added, the mixture is stirred for a further 10 minutes and a solution of 28.5 g of N-ethyl-N-.beta.-(.beta.-phenoxyethyloxy)-ethyl-aniline in a mixture of 100 ml of propionic acid, 50 ml of glacial acetic acid and 10 g of 78% strength sulphuric acid is then introduced at -5.degree. C. The mixture is stirred for a further hour at -10.degree. C and diluted with water to approx. 600 ml and the product is filtered off. The azo dyestuff is suspended in water and the suspension is neutralised with sodium hydroxide solution. The product is then again filtered off, washed with water and dried in vacuo. The resulting black-violet powder is stirred into 150 ml of chloroform and 25 g of dimethyl sulphate are added dropwise at the boiling point of the chloroform. The mixture is then stirred for a further 90 minutes under reflux cooling and 900 ml of boiling water are then introduced. Hereupon, the chloroform distils off.

#40 g of sodium chloride are added to the resulting solution at 50.degree. C, the mixture is cooled and the dyestuff which has crystallised out is filtered off and dried in vacuo. It has the formula ##STR17## and dyes polyacrylonitrile fibres in a blue colour shade of outstanding fastness properties.

#The dyestuff can also be prepared by carrying out the quaternisation with p-toluenesulphonic acid methyl ester or with methyl idodide instead of with dimethyl sulphate.

Facts

Application

05/539,778Filed 9 Jan 1975

Priority

DT 240124611 Jan 1974

Granted

27 Sep 1977

Term ended

27 Sep 1994

Estimated · how

Pre-1995 term; greater of 17 years from grant or 20 years from filing when eligible. Maintenance-fee lapses, terminal disclaimers and statutory extensions have not been checked. The continuity chain may be incomplete; this is not an enforceability determination.

Classification3 codes

C09B 44/20
Containing cyclammonium groups attached to an azo group by a carbon atom of the ring system: thiazoles or hydrogenated thiazoles
C09B 44/04
Containing ammonium groups not directly attached to an azo group: from coupling components containing amino as the only directing group
C09B
Organic dyes or closely-related compounds for producing dyes

Cationic dyestuffs

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Cationic dyestuffs

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Abstract

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Claims7

Description6,123 words

Drawings

Classification3 codes

Life of this patent

Description6,123 words