US 4,302,387 A · Azo dyes from 1,3,4-thiadiazol-2-yl and 1,2,4-thiadiazol-5-yl moieties bearing sulfated hydroxyalkoxycarbonyl or N-(hydroxyalkyl)carbamoyl groups on their rings

Abstract

This invention relates to azo dyes in which the diazotized amino component bears sulfated hydroxyalkoxycarbonyl or N-(hydroxyalkyl)carbamoyl groups on its ring. These dyes have excellent dyeing properties on polyamide fibers and also impart color to cellulose acetate fibers and wool. The dyes correspond to the general formulae: ##STR1## wherein X' is O, NH, N(alkyl)-- or N(aryl)--; Z is selected from straight- or branched-chain alkylene which may be substituted, for example, with phenyl, halogen, OSO.sub.3 M, alkoxy, aryloxy and the like; M is H, Na, K or NH.sub.4 ; and the coupler C is selected from those of the formulae ##STR2## wherein the R substituents are selected from a wide variety of groups known to the art.

A dye of the formula:

##STR44## and wherein C is a coupler selected from ##STR45## wherein R.sup.2 and R.sup.14 each represents up to three groups selected from hydrogen, fluorine, chlorine, bromine, alkyl, cycloalkyl, alkoxy, phenoxy, alkylthio, arylthio, and radicals having the formula --NH--X--R.sup.3 in which X is --CO--, --COO--, or --SO.sub.2 -- and R.sup.3 is selected from alkyl and alkyl substituted with halogen, hydroxy, phenoxy, aryl, cyano, cycloalkyl, alkylsulfonyl, alkylthio, alkanoyloxy, and alkoxy, and when X is --CO--, R.sup.3 also is selected from hydrogen, amino, alkylamino, dialkylamino, arylamino, aryl, and furyl;
R.sup.4 and R.sup.5 are each selected from hydrogen, alkyl, aryl, cycloalkyl, and alkyl substituted with halogen, CN, OH, alkoxy, aryloxy, alkoxyalkoxy, alkanoyl, alkanoyloxy, carbamoyl, alkylcarbamoyl, sulfamoyl, alkylsulfamoyl, alkoxyalkanoyloxy, and cycloalkyl, and R.sup.4 and R.sup.5 together represent a single, combined group --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 --S--CH.sub.2 CH.sub.2 --, or --CH.sub.2 CH.sub.2 --SO.sub.2 --CH.sub.2 CH.sub.2 --;
R.sup.8 represents one or two groups each selected from hydrogen, alkyl and alkyl substituted with --CN, alkoxy, alkoxycarbonyl, alkoxycarbonyloxy, phenyl, cyclohexoxy, --OH, --Cl and Br;
R.sup.9, R.sup.10 and R.sup.11 are each selected from hydrogen, alkyl, phenyl, or phenyl substituted with 1-3 groups selected from Cl, Br, alkyl or alkoxy, alkylthio, benzylthio, cyclohexylthio and phenylthio;
Q and Q' are each selected from --CO--, --SO.sub.2 --, or --CN;
R.sup.12 and R.sup.13 are each selected from alkyl, hydroxyalkyl, alkoxy, alkoxycarbonylamino, trifluoromethyl, phenyl or phenyl substituted with 1-3 groups selected from Cl, Br, alkyl or alkoxy, alkoxycarbonylalkyl, cyanoalkyl, amino, haloalkyl, alkylamino, alkylthio, benzylthio, cyclohexylthio and phenylthio;
and R.sup.12 and R.sup.13 together comprise --CH.sub.2 C(CH.sub.3).sub.2 CH.sub.2 --, or 1,2--C.sub.6 H.sub.4 -- connecting Q and Q';
R.sup.16 and R.sup.17 are selected from hydrogen, cycloalkyl, aryl, alkyl, and alkyl substituted with alkoxy, hydroxy, alkoxyalkoxy, hydroxyalkoxy, carbamoyl, sulfamoyl, alkanoylamino, or alkenylsulfonyl, and aryl substituted with hydroxyalkyl;
e is 1 or 2;
t and t' are each 1 or zero;
X' is O, NH, N(alkyl)--, or N(aryl)--;
Z is selected from straight- or branched-chain alkylene, and such alkylene substituted with phenyl, halogen, OSO.sub.3 M, alkoxy or aryloxy groups, --CH.sub.2 (CH.sub.2).sub.m V--CH.sub.2 (CH.sub.2).sub.p --, where m is 1, 2 or 3, p is 0, 1, 2 or 3, and V is O, S, SO.sub.2, --SO.sub.2 NH--, --SO.sub.2 N(alkyl)--, --SO.sub.2 N(aryl), --N(SO.sub.2 aryl)--, --NH, --NHCO--, -- NHCONH, --N(SO.sub.2 alkyl), or --CON(alkyl);
M is H, Na, K or NH.sub.4 ;
n is 1 or 2;
and wherein each of the above alkyl and alkoxy groups contain from 0 to three of the following:
hydroxy;
halogen;
cyano;
succinimido;
glutarimido;
phthalimido;
2-pyrrolidino;
cyclohexyl;
phenyl or phenyl substituted with alkyl, alkoxy, halogen, alkanoylamino, cyano or alkoxycarbonyl;
alkanoylamino;
sulfamoyl;
alkylsulfamoyl;
vinylsulfonyl;
acrylamido;
phthalimidinyl;
benzoylsulfonicimidyl;
alkylsulfonamido;
phenylsulfonamido;
alkoxycarbonylamino;
alkylcarbamoyloxy;
alkoxycarbonyl;
alkoxycarbonyloxy;
##STR46## wherein Y is --NH--, --NH--alkyl--, --O--, --S--, or --CH.sub.2 O--;
--S--R.sup.6, wherein R.sup.6 is alkyl, phenyl, phenyl substituted with halogen, alkyl, alkoxy, alkanoylamino, cyano, or alkoxycarbonyl, pyridyl, pyrimidinyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, or ##STR47## --SO.sub.2 R.sup.3 ;
--COOR.sup.3 ;
--OXR.sup.3 ;
--NH--X--R.sup.3 ;
--X--R.sup.3 ;
--SO.sub.2 NR.sup.7 R.sup.7 ;
wherein R.sup.3 and X are as defined above and each R.sup.7 is selected from H and R.sup.3 ;
alkoxy;
alkoxy substituted with hydroxy, cyano, alkanoyloxy, or alkoxy;
phenoxy;
or phenoxy substituted with one or more of alkyl, alkoxy or halogen.

46 more elements

Azo dyes from 1,3,4-thiadiazol-2-yl and 1,2,4-thiadiazol-5-yl moieties bearing sulfated hydroxyalkoxycarbonyl or N-(hydroxyalkyl)carbamoyl groups on their rings

Life of this patent

Azo dyes from 1,3,4-thiadiazol-2-yl and 1,2,4-thiadiazol-5-yl moieties bearing sulfated hydroxyalkoxycarbonyl or N-(hydroxyalkyl)carbamoyl groups on their rings

Life of this patent

Abstract

Claims4