US 4,785,099 A · Water-soluble triphendioxazine compounds

Abstract

Water-soluble triphendioxazine compounds having fiber-reactive dye properties and the general formula (1) ##STR1## in which the meanings are: T is a substituted or unsubstituted alkyl of 1 to 6 carbon atoms, except an ethyl which is substituted in the .beta.-position by an alkalinically eliminatable substituent, which alkyl can be interrupted by --O--, --S--, --NH-- and --N(R')-- where R' is equal to substituted or unsubstituted alkyl of 1 to 6 carbon atoms, or is substituted or unsubstituted aryl, B is --O--, --S--, --NH-- or --N(R")-- where R" is equal to substituted or unsubstituted alkyl, W is a bridge member or W and B together form a direct bond, R is hydrogen or a substituent, R* is hydrogen or a substituent or R* and W, if W contains an amino group, or a portion of W form together with the nitrogen atoms the radical of a heterocycle, A is a non-heterocyclic fiber-reactive group or a 2-halogeno-s-triazin-6-yl radical which is substituted in the 4-position by halogen or a substituted or unsubstituted amino group which can also contain a fiber-reactive group, or by a heterocyclic radical or by a further such halogenotriazinyl radical bonded via an amino radical as bridge member, X.sup.1 and X.sup.2 are each hydrogen, halogen, cycloalkyl, aralkoxy, alkoxy, aryloxy, alkyl, aryl, aralkyl, cyano, carboxy, carbalkoxy, arylamino, carbamoyl and alkylmono- or -disubstituted carbamoyl or arylcarbamoyl, alkanoylamino or aroylamino, which aryl radicals can in each case be substituted; of the sulfo and sulfate groups the molecule mandatorily contains at least one of these groups, furthermore precursors of the formulae ##STR2## with B* equal to --NH-- or --N(R")-- and R, R*, W and T of the abovementioned meanings. The triphendioxazine compounds serve for dyeing chiefly wool and synthetic polyamide fibers and in particular cellulose fibers by means of application and fixing methods which are customary for fiber-reactive dyes.

A water-soluble triphendioxazine compound of the formula ##STR94## in which:

T is alkyl of 1 to 6 C-atoms unsubstituted by 1 or 2 substitutuents selected from the group consisting of chlorine, alkoxy of 1 to 4 C-atoms, alkanoylamino of 2 to 5 C-atoms, cyano, sulfato, phosphato, acetyloxy, sulfo, carboxy, phenyl and naphthyl, the phenyl and naphthyl each being unsubstituted or substituted by substituents selected from the group consisting of alkyl of 1 to 4 C-atoms, alkoxy of 1 to 4 C-atoms, halogen, sulfo, carboxy, sulfamoyl, carboamoyl, carboamoyl mono- or disubstituted by substituents selected from the group consisting of phenyl, alkyl of 1 to 4 C-atoms, phenylakyl with alkyl of 1 to 4 C-atoms and cycloalkyl of 5 to 8 C-atoms, sulfamoyl mono- or disubstituted by substituents selected from the group consisting of phenyl, alkyl of 1 to 4 C-atoms, phenylalkyl with alkyl of 1 to 4 C-atoms and cycloalkyl of 5 to 8 C-atoms, trifluoromethyl, alkanoylamino of 2 to 5 C-atoms, nitro, amino and amino mono- or disubstituted by substituents selected from the group consisting of alkyl of 1 to 6 C-atoms, phenyl, naphthyl and cycloalkyl of 5 to 8 C-atoms, and the alkyl group T is interrupted or is not interrupted by hetero groups selected from groups consisting of --O--, --S--, --NH--and --N(R')--in which R' is alkyl of 1 to 6 C-atoms unsubstituted or substituted by one or two substituents selected from the group consisting of chlorine, alkoxy of 1 to 4 C-atoms, alkanoylamino of 2 to 5 C-atoms, cyano, sulfato, phosphato, acetyloxy, sulfo, carboxy, phenyl and naphthyl,
with the proviso that T, as a substituted alkyl, is not an ethyl group which is substituted in the .beta.-position by a substituent which is eliminated by an alkali, or
T is phenyl or naphthyl, or phenyl or naphthyl each substituted by substituents selected from the group consisting of alkyl or 1 to 4 C-atoms, alkoxy of 1 to 4 C-atoms, halogen, sulfo, carboxy, sulfamoyl, carbamoyl, carboamoyl mono- or disubstituted by substituents selected from the group consisting of phenyl, alkyl of 1 to 4 C-atoms, phenylalkyl with alkyl of 1 to 4 C-atoms and cycloalkyl of 5 to 8 C-atoms, sulfamoyl mono- or disubstituted by substituents selected from the group consisting of phenyl, alkyl of 1 to 4 C-atoms, phenylalkyl with alkyl of 1 to 4 C-atoms and cycloalkyl of 5 to 8 C-atoms, trifluoromethyl, alkanoylamino of 2 to 5 C-atoms, nitro, amino and amino mono- or disubstituted by substituents selected from the group consisting of alkyl of 1 to 6 C-atoms, phenyl, naphthyl and cycloalkyl of 5 to 8 C-atoms;
B is oxygen or sulfur or a group of the formula --NH-- or --N(R")-- in which R" is alkyl of 1 to 6 C-atoms unsubstituted or substituted by 1 or 2 substituents selected from the group consisting of chlorine, alkoxy of 1 to 4 C-atoms, alkanoylamino of 2 to 5 C-atoms, cyano, sulfato, phosphato, acetyloxy, sulfo, carboxy, aryl unsubstituted or substituted by carboxy or sulfo, and cycloalkyl of 5 to 8 C-atoms, or
B forms together with W a direct covalent bond;
W forms together with B a direct covalent bond or
W is phenylene or naphthylene, or phenylene or naphthylene substituted by substituents selected from the group consisting of alkyl of 1 to 4 C-atoms, alkoxy of 1 to 4 C-atoms, halogen, sulfo, carboxy, sulfamoyl, carboamoyl, carbamoyl mono- or disubstituted by substitutents selected from phenyl, alkyl of 1 to 4 C-atoms, phenylakyl having an alkyl of 1 to 4 C-atoms and cycloalkyl of 5 to 8 C-atoms, sulfamoyl mono- or disubsitituted by phenyl, alkyl of 1 to 4 C-atoms, phenylakyl having an alkyl of 1 to 4 C-atoms and cycloakyl of 5 to 8 C-atoms, trifluoromethyl, alkanoylamino of 2 to 5 C-atoms and nitro;
R is hydrogen or alkyl of 1 to 4 C-atoms or alkoxy of 1 to 4 C-atoms or halogen;
R* is hydrogen or alkyl of 1 to 4 C-atoms unsubstituted or substituted by 1 or 2 substitutents selected from the group consisting of chlorine, alkoxy of 1 to 4 C-atoms, alkanoylamino of 2 to 5 C-atoms, cyano, sulfato, phosphato, acetyloxy, sulfo, carboxy, aryl unsubstituted or substituted by carboxy or sulfo, and cycloalkyl of 5 to 8 C-atoms, or is cycloalkyl of 5 to 8 C-atoms, or
R* and R.sup.o form together with both nitrogen atoms and with W or a part of W a 5- or 6-membered saturated heterocyclic ring;
A is a non-heterocyclic fiber-reactive group selected from .beta.-chloropropionyl, 3-(.beta.-chloroethylsulfonyl)-benzoyl and 2-fluoro-2-chloro-3,3-difluoro-cyclobutane-1-carbonyl, or
A is a group of the general formula ##STR95## in which Z is chlorine and
Y is an amino group of the formula ##STR96## in which R.sup.1 is hydrogen or alkyl or 1 to 4 C-atoms unsubstituted or substituted by 1 or 2 substituents selected from the group consisting of:
alkoxy of 1 to 4 C-atoms;
chlorine;
cyano;
carboxy;
sulfo;
sulfato;
phosphato;
hydroxy;
phenyl unsubstituted or substituted by 1, 2 or 3 substitutents selected from the set of groups consisting of 3 alkyl groups of 1 to 4 C-atoms, 2 alkoxy groups of 1 to 4 C-atoms, 1 bromine atom, 2 chlorine atoms, 2 sulfo groups and 1 carboxy group;
naphthyl unsubstituted or substituted by 1, 2 or 3 sulfo groups;
and 1 group of the formula (4a), (4b), (5a) or (5b) ##STR97## in which E is a substituent which is eliminated by means of an alkali, and
Alk is hydrogen or alkyl of 1 to 4 C-atoms,
or R.sup.1 is cycloalkyl of 5 to 8 C-atoms, and
R.sup.2 is hydrogen or alkyl of 1 to 4 C-atoms unsubstituted or substituted by 1 or 2 substituents selected from the group consisting of:
alkoxy of 1 to 4 C-atoms;
chlorine;
cyano;
carboxy;
sulfo;
sulfato;
phosphato;
hydroxy;
phenyl unsubstituted or substituted by 1, 2 or 3 substitutents selected from the set of groups consisting of 3 alkyl groups of 1 to 4 C-atoms, 2 alkoxy groups of 1 to 4 C-atoms, 1 bromine atom, 2 chlorine atoms, 2 sulfo groups and 1 carboxy group;
naphthyl unsubstituted or substituted by 1, 2 or 3 sulfo groups;
and 1 group of the formula (4a), (4b), (5a) or (5b) defined above, or
R.sup.2 is cycloalkyl of 5 to 8 C-atoms, or is phenyl unsubstituted or substituted by 1 , 2 or 3 substituents selected from the set consisting of 3 alkyl groups of 1 to 4 C-atoms, 2 alkoxy groups of 1 to 4 C-atoms, 1 bromine atom, 2 chlorine atoms, 2 sulfo groups, 1 carboxy group and 1 group of the formula (4a), (4b), (5a) or (5b) mentioned and defined bove, or is naphthyl unsubstituted or substituted by 1, 2 or 3 substituents selected from the set consisting of 2 sulfo groupos and 1 groups and 1 group fo the formula (4a), (4b), (5a) or (5b) mentioned nad defined above,
at least one of those substituents in R.sup.1 and R.sup.2 is mandatorily a group of the above-mentioned formulae (4a), (4b), (5a) and (5b),
or R.sup.1 and R.sup.2 form together with the N-atom the group piperidino, morpholino or piperazino;
X.sup.1 is hydrogen, halogen, cycloalkyl of 5 to 8 C-atoms, aralkoxy, alkoxy of 1 to 4 C-atoms, aryloxy, alkyl of 1 to 4 C-atoms, aryl, aralkyl, cyano, carboxy, carbalkoxy of 2 to 5 C-atoms, arylamino, carboamoyl, N-alkyl-carbamoyl with alkyl of 1 to 4 C-atoms, N,N-dialkyl-carboamoyl with alkyl each of 1 to 4 C-atoms, N-aryl-carbamoyl, alkanoylamino of 2 to 5 C-atoms or arylamino, the mentioned aryls in the mentioned groups being unsubstituted or substittued by 1 or 2 substituents selected from the group consisting of halogen, nitro, alkyl of 1 to 4 C-atoms, alkoxy of 1 to 4 C-atoms, carboxy and sulfo;
X.sup.2 is identical to or different from X.sup.1 and has one of the meanings indicated for X.sup.1 ;
at least one of the groups selected from sulfo and sulfato, which may be present according to the above definitions, is mandatorily present in the triphenodioxazine compound.

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Water-soluble triphendioxazine compounds

Life of this patent

Water-soluble triphendioxazine compounds

Life of this patent

Abstract

Claims6