Abstract:
Water-soluble triphendioxazine compounds of the formula ##STR1## having at least one sulfato or sulfo group, in which R is a hydrogen atom, a water-solubilizing group, an alkyl group having 1 to 6 carbon atoms which is substituted by an acidic group, or an optionally substituted sulfonamide group,B is an oxygen or sulfur atom or a group of the formula --NH--or --N(R')--, where R' equals optionally substituted alkyl, cycloalkyl which is optionally substituted by certain substituents, or optionally substituted phenyl, or naphthyl which is optionally substituted by sulfo and/or a --SO.sub.2 --Y' group,B.sup.1 has one of the meanings stated for B and is identical to B or different from B,W is a bivalent aliphatic, araliphatic or aromatic radical which may be interrupted by 1 or 2 hetero groups from the series comprising groups of the formulae --O--, --NH--and --N(R')--, where R' has the above meaning,W.sup.1 has one of the meanings stated for W and is identical to W or different from W,T is a hydrogen atom or sulfo, sulfato, phosphato or carboxy,T.sup.1 has one of the meanings stated for T and is identical to T or different from T and T.sup.1 is necessarily a water-solubilizing group when R denotes hydrogen,R.sup.3 R.sup.4, identical or different, are each hydrogen, alkyl, alkoxy, halogen, carboxy or sulfo,X.sup.1 is hydrogen, halogen, cycloalkyl, arylkyloxy, alkoxy, aryloxy, alkyl, aryl, aralkyl, cyano, carboxyl, carbalkoxy, N-alkyl-substituted carbamoyl or N-aryl-substituted carbamoyl, alkanoylamino or optionally substituted aroylamino,X.sup.2 has one of the meanings stated for X.sup.1 and is identical to X.sup.1 or different from X.sup.1,Y is vinyl or ethyl which is substituted in the .beta. position by a substituent which can be eliminated by means of an alkali,Y' has one of the meanings stated for Y and is identical to Y or different from Y.These new compounds have fiber-reactive dyestuff properties and are particularly suitable for dyeing cellulose fiber materials so that they are fast.
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 orW 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.
Abstract:
Water-soluble triphendioxazine compounds which have fiber-reactive properties as dyestuffs, which afford deep and fast dyeings on fiber materials, such as wool and, in particular, cellulose, and which correspond to the formula (1) ##STR1## in which: n is the number 0 or 1;Y is the vinyl group or an ethyl group containing, in .beta.-position, a substituent which can be eliminated by means of an alkali;Q.sup.1 and Q.sup.2 both represent a benzotriazole radical which can also be additionally substituted in the benzene nucleus by alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, halogen, carboxy or sulfo;B is --O--, --S--, --NH--or --N(R')--wherein R' is optionally substituted alkyl having 1 to 6 carbon atoms;W.sup.1 and W.sup.2 both represent a divalent, optionally substituted aliphatic, cycloaliphatic, aliphatic-cycloaliphatic, araliphatic or aromatic-carbocyclic radical, it being possible for the aliphatic radicals to be interrupted by hetero groups --O--, --S--, --SO.sub.2 --, --CO--, 1,4-piperidino, --NH--and/or --N(R.sup.o)--in which R.sup.o is optionally substituted alkyl having 1 to 6 carbon atoms or alkanoyl having 2 to 5 carbon atoms, and/or for aliphatic and aryl radicals to be attached to one another through such a hetero group;R is hydrogen, alkyl having 1 to 6 carbon atoms, alkoxy having 1 to 6 carbon atoms, halogen, carboxyl or sulfo;E is hydrogen, sulfo, carboxyl, a group --SO.sub.2 --Y as defined above or an optionally substituted sulfonamide group; andX.sup.1 and X.sup.2 are both hydrogen, cycloalkyl, alkoxy, aryloxy, aryl or another substituent;and at least one carboxy, sulfo or sulfato group is present in the molecule (1),and pre-products of those triphendioxazine compounds, of the general formula ##STR2## in which K is an amino or nitro group, Y' is .beta.-hydroxyethyl or defined as for Y, W has one of the meanings of W.sup.1, and E' is hydrogen, sulfo, carboxy or a group of the formula --SO.sub.2 --Y' defined above, or an optionally substituted sulfonamide group, and R, B and R* have the above meanings.
Abstract:
N.sub.1 -substituted 1H-benzotriazole hydroxyethyl sulfone compounds, a process for their preparation and their use for the preparation of dyestuffs. Compounds of the general formula ##STR1## in which R is hydrogen or alkyl which has 1 to 6 carbon atoms and can be substituted by hydroxy, sulfo, carboxy, phosphono and/or cyano, W denotes a divalent, optionally substituted aliphatic radical, (C.sub.5 -C.sub.10)-cycloaliphatic radical which is optionally substituted by alkyl, aliphatic-(C.sub.5 -C.sub.8)-cycloaliphatic radical which is optionally substituted by alkyl, optionally substituted araliphatic radical or optionally substituted aromatic carbocyclic radical, it being possible for the aliphatic radicals in W to be interrupted by hetero groups of the formulae --O--, --S--, --SO.sub.2 --, --CO--, 1,4-piperidino, --NH-- and --N(R')-- in which R' is an alkyl group which has 1 to 6 carbon atoms and can be substituted, or is an alkanoyl group having 2 to 5 C atoms, and/or for the aliphatic radicals and aryl radicals to be attached to one another through such a hetero group, and R* denotes hydrogen, alkyl having 1 to 6 carbon atoms, alkoxy having 1 to 5 carbon atoms, halogen, carboxy or sulfo.They are used as intermediates for the preparation of dyestuffs, such as fiber-reactive triphendioxazine dyestuffs, and can be prepared by reducing the nitro group in a compound of the general formula ##STR2## in which R, R* and W have the abovementioned meaning and A is a hydrogen atom or an acyl radical, to the amino group and diazotizing this amino group, whereupon cyclization takes place to give the benzotriazole, and, if necessary, subsequently eliminating the acyl radical by hydrolysis.
Abstract:
Triphendioxazine compounds with properties of fiber-reactive dyestuffs corresponding to the general formula ##STR1## in which T is an optionally substituted alkyl group with 1 to 6 carbon atoms, excluding a radical of the group Y defined below, it also being possible for the alkyl group to be interrupted by hetero atoms, or is an optionally substituted aryl group,B is an oxygen or sulfur atom or an amino group,W is a divalent, optionally substituted aliphatic, cycloaliphatic, araliphatic or aromatic-carbocyclic radical or a benzotriazole radical combined with one of these radicals, it being possible for the aliphatic radicals to be interrupted by hetero groups and/or for aliphatic and aryl radicals to be bonded to one another by a hetero group,R is hydrogen, alkyl with 1 to 6 carbon atoms, alkoxy with 1 to 5 carbon atoms, halogen, carboxy or sulfo,X.sup.1 is hydrogen, halogen, cycloalkyl, aralkyloxy, alkoxy, aryloxy, alkyl, aryl, aralkyl, cyano, carboxy, carbalkoxy, arylamino, carbamoyl, which is optionally substituted, alkanoylamino or aroylamino,X.sup.2 can have the meaning of X.sup.1,n represents the number 1 or 2,Y is the vinyl group or an ethyl group which is substituted in the .beta.-position by a substituent which can be eliminated with an alkaliand the molecule (1) contains at least one sulfo or sulfato group.
Abstract:
Water-soluble triphendioxazine compounds which have valuable fiber-reactive dyestuff properties and correspond to the general formula (1) and dye materials, in particular cellulose fiber materials, containing carboxamide and/or hydroxy groups in fast shades. ##STR1## in which: B is a group --O--, --S--, --NH-- or --N(R')-- in which R' is alkyl having 1 to 6 carbon atoms;R* is hydrogen or optionally substituted lower alkyl or optionally substituted aryl;W and W.sup.1 independently of one another are each a divalent aliphatic radical or a cycloaliphatic radical which is optionally substituted by lower alkyl or an aliphatic-cycloaliphatic radical which is optionally substituted by lower alkyl, it being possible for the aliphatic radicals to be interrupted by one or more groups --O--, --S--, --SO.sub.2 --, --CO--, 1,4-piperidino, --NH-- and --N(R.sup.o)-- in which R.sup.o has the meaning of R' or is lower alkanoyl;the groupings --B--W.sup.1 --N(R*)-- and --N(R*)--W--B 13 independently of one another each represent the divalent radical of a five-membered or six-membered, saturated heterocyclic structure containing two N atoms, or the groupings --B--W.sup.1 -- and --W--B-- independently of one another each represent the divalent radical of a five-membered or six-membered, saturated heterocyclic structure which contains two N atoms and which is attached by means of one of the two N atoms, via a C.sub.2 -C.sub.4 -alkylene, to the groupings --N(R*)--A or A--N(R*)--, respectively;is benzoyl, naphthoyl, N-phenylcarbamoyl or N-naphthylcarbamoyl in which the phenyl and naphthyl radicals can be substituted, at least one of these being a group which imparts solubility in water;X.sup.1 and X.sup.2 independently of one another are each hydrogen, halogen, lower alkyl, lower alkoxy or optionally substituted aryl;Y is vinyl or a .beta.-substituted ethyl;and the compounds necessarily contain at least two sulfo groups.
Abstract:
Copper complex formazan compounds which have fiber-reactive properties and are very highly suitable for use as dyes for dyeing carboxamido-containing and/or hydroxy-containing material, such as fiber material, for example wool and cellulose fiber materials, have the general formula (1) ##STR1## where A is a benzene or naphthylene ring which may be substituted by substituents customary in dyes, such as halogen, nitro, alkyl and alkoxy,B is alkylene of 1 to 8 carbon atoms or alkenylene of 2 to 8 carbon atoms which may each be substituted by phenyl which in turn may contain the substituents customary in dyes, or is alkylene-phenylene or alkenylene-phenylene having lower alkylene and alkenylene radicals, while the phenylene radicals may in turn contain the substituents customary in dyes, or is a phenylene or naphthylene radical which may contain substituents customary in dyes, or is the bivalent radical of a heterocycle, such as furan, thiophene or benzimidazole, or--B--Z together is hydrogen,Z is a water-solubilizing group, such as sulfo,k is 1 or 2,m is 0, 1 or 2,n is 0, 1 or 2, the sum (m+n) is 1 to 4;X is oxygen or carbonyloxy,R is hydrogen or substituted or unsubstituted lower alkyl,D is substituted or unsubstituted phenylene or naphthylene,Y is vinyl or an ethyl group which contains in the .beta.-position a substituent which is eliminatable under alkaline conditions, andM is hydrogen, an alkali metal or an alkaline earth metal.
Abstract:
Water-soluble copper complex formazan compounds which conform to the general formula (1) below and have useful fiber-reactive dye properties and dye carboxamido- and/or hydroxy-containing material, in particular cellulose fibers, in fast blue shades. ##STR1## in which: M is hydrogen or a salt-forming metal atom,k, m and n each denote the number zero, 1 or 2, the sum (k+m+n) being equal to 1 to 4,A is a benzene or napththalene ring which additionally can contain the fiber-reactive group --NH--Q and further substituents,B is a benzene or naphthalene ring which additionally contains the fiber-reactive group --NH--Q and further substituents,D is substituted or unsubstituted alkylene of 1 to 8 carbon atoms or is a benzene or naphthalene ring having optionally additional substituents or is a heterocyclic radical,X is a sulfo group or an oxy or carbonyloxy group,r is the number 1 or 2,Q is a radical of the formula (2) ##STR2## in which Y is halogen, Z is vinyl or a .beta.-substituted ethyl,G is the thio or an amino group --N(R)-- where R is equal to hydrogen or to low, substituted or unsubstituted alkyl or a group --K--W.sub.p defined hereinafter, K is alkylene or arylene or arylene-alkylene or alkylene-arylene whose arylene and alkylene radicals can be substituted and/or interrupted by a hetero group, W is a water-solubilizing group and p is the number 1, 2 or 3,the group --NH--Q is bonded to an aromatic carbon atom of A or B or D or to an aliphatic carbon atom of D or of a substituent on A or B, in the case of r=2, however, not simultaneously to A, B or D.
Abstract:
Precursors for the preparation of fiber-reactive triphendioxazine dyestuffs correspond to the general formulas: ##STR1## in which Y' is a vinyl, a beta-hydroxyethyl or an ethyl group which contains in the beta-position a substituent which can be eliminated by an alkali;T is an optionally substituted alkyl (e.g. substituted with hydroxy) with 1-6 carbon atoms, preferably 1 to 4 carbon atoms, excluding a radical of the group Y' defined above, it also being possible for the alkyl group to be interrupted by hetero groups, preferably 1 to 2 hetero groups, selected from groups of the formulae --O--, --S--, --NH-- and --N(R')--, where R' has the meaning given below, or T is an optionally substituted aryl group;B is an oxygen or sulfur atom or an amino group of the formula --NH-- or --N(R')--, in whichR' is an alkyl group with 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, such as, in particular, the methyl or ethyl group, which can be substituted;W is a divalent, optionally substituted aliphatic, optionally alkyl-substituted (C.sub.5 -C.sub.10)-cycloaliphatic, optionally alkyl-substituted aliphatic-(C.sub.5 -C.sub.8)-cycloaliphatic, optionally substituted araliphatic or optionally substituted aromatic-carbocyclic radical or a benzotriazole radical combined with one of these radicals, it being possible for the aliphatic radicals in W to be interrupted by hetero groups, preferably 1 to 2 hetero groups, selected from the groups --O--, --S--, --SO.sub.2 --, --CO--, 1,4-piperidino, --NH-- and --N(R.sup.o)--, in which R.sup.o has one of the meanings of R' or is an alkanoyl group with 2 to 5 carbon atoms, such as an acetyl group, and/or it being possible for aliphatic and aryl radicals to be linked to one another by such a hetero group;R' is a hydrogen atom or alkyl with 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, such as, in particular, methyl and ethyl of these, alkoxy with 1 to 5 carbon atoms, preferably 1 to 4 carbon atoms, such as, in particular, methoxy and ethoxy of these, halogen, such as fluorine or bromine or, in particular, chlorine, carboxy or sulfo;n is the number 1 to 2, but is preferably 1.
Abstract:
Water-soluble triphendioxazine compounds having fiber-reactive dye properties conforming to the general formula ##STR1## where: B is --O-- or --S-- or --NH-- or (C.sub.1 -C.sub.6)-alkylamino;R* is hydrogen or optionally substituted alkyl or aryl;W and W.sup.1 are each a bivalent, aliphatic or optionally alkyl-substituted cycloaliphatic or aliphatic-cycloaliphatic radical, which aliphatic radicals can be interrupted by --O--, --S--, sulfonyl, carbonyl, 1,4-piperidino, amino, alkylamino and/or alkanoylamino groups, orthe grouping --B--W.sup.1 --N(R*) and/or --N(R*)--W--B-- each represent the bivalent radical of a five- or six-membered saturated heterocycle which contains two nitrogen atoms, orthe grouping --B--W.sup.1 -- and/or --W--B-- each represent the bivalent radical of a five- or six=-membered saturated heterocycle which contains two nitrogen atoms and which is bonded by one of the two nitrogen atoms via an alkylene group of 2 to 4 carbon atoms to the grouping --N(R*)--CO--G.sup.1 -- or --G--CO--A--N(R*);G and G.sup.1 are each a direct bond or a (C.sub.1 -C.sub.8)-alkylene or aliphatic-cycloaliphatic or cycloaliphatic radical;M is hydrogen, alkali metal or alkaline earth metal;X.sup.1 and X.sup.2 are each hydrogen, halogen, alkyl, alkoxy, aryloxy or optionally substituted aryl;Y is vinyl or ethyl having an alkali-eliminable substituent in the .beta.-position,and also precursors thereof, conforming to the general formula ##STR2## where Q is the nitro or amino group, B, R* and M have the above meanings, Y' has a meaning of Y or is equal to .beta.-hydroxyethyl and K has the above meaning of G or, if Q is equal to NO.sub.2, is also equal to alkenylene of 2 to 8 carbon atoms or alkdienylene of 4 to 8 carbon atoms.The triphendioxazine compounds serve as dyes for dyeing carboxamido-containing fiber materials, in particular hydroxyl-containing fiber materials, such as cellulose; they produce strong, fast, blue dyeings.