Abstract:
Water-soluble monoazo compounds of the general formula (1) which dye in fast, mainly red shades materials which contain carboxamide and/or hydroxy groups, preferably in the form of fibers, in particular cellulose fiber materials. ##STR1## in which: Y is .beta.-thiosulfatoethyl, .beta.-phosphatoethyl, .beta.-chloroethyl, vinyl or .beta.-sulfatoethyl,M is hydrogen, an alkali metal or an alkaline-earth metal,D is naphthyl which is substituted by sulfo and/or a group of the formula Y--SO.sub.2 --,or is one of the radicals ##STR2## in which M and Y have one of the above meanings, m is the number zero or 1, R.sup.1 is hydrogen, lower alkyl, lower alkoxy or carboxy, and R.sup.2 is hydrogen, lower alkyl, lower alkoxy, sulfo, carboxy, optionally substituted aryl, hydroxy, nitro or halogen,n is the number zero or 1,R is hydrogen or optionally substituted lower alkyl,R* is hydrogen or optionally substituted lower alkyl,X is fluorine or chlorine,B is a group of the formula ##STR3## in which R.sup.3 is hydrogen or optionally substituted lower alkyl or aryl, R.sup.4 is hydrogen, optionally substituted alkyl having 1 to 8 carbon atoms or cycloalkyl having 5 to 8 carbon atoms and optionally having 1 to 3 methyl groups and/or one amino, lower alkanoylamino or benzoylamino group as substituents, or is the phenyl radical which may be substituted by sulfo, carboxy, halogen, lower alkyl, lower alkoxy, nitro, a group of the formula --SO.sub.2 --Y' (where Y' has one of the meanings of Y or is .beta.-hydroxyethyl), lower alkylamino, lower dialkylamino, lower alkanoylamino and/or benzoylamino, or is naphthyl radical, which may be substituted by sulfo and/or a group of the formula --SO.sub.2 --Y', and R.sup.5 has one of the meanings specified for R.sup.4, or R.sup.4 and R.sup.5, together with the nitrogen atom and one, two or three lower alkylene radicals and, if appropriate, one or two further heteroatoms, form a lower heterocyclic radical.
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.
Abstract:
Water-soluble compounds having fiber-reactive dye properties of the general formula ##STR1## in which A is an alkylene of 2 to 6 carbon atoms or a phenylene which can be substituted by 1 or 2 substituents, or is a radical of the formula ##STR2## in which W is a direct bond or a bridge member and the R' and R* each denote hydrogen, chlorine, methyl, methoxy, ethoxy, carboxy or sulfo;B is chlorine or fluorine;R is hydrogen, chlorine, an alkyl of 1 to 4 carbon atoms or an alkoxy of 1 to 4 carbon atoms;M is hydrogen or an alkali metal;n stands for the number zero, 1 or 2,K is a radical of the formula ##STR3## in which D is phenylene which can be substituted by chlorine, bromine, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, carboxy or sulfo, or is naphthalene with optionally 1 or 2 sulfo groups,R.sup.1 denotes hydrogen, chlorine, alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms,R.sup.2 is hydrogen or alkyl of 1 to 4 carbon atoms,G is carboxy, methyl or carbalkoxy of 2 to 5 carbon atoms,Y denotes vinyl, .beta.-sulfatoethyl, .beta.-phosphatoethyl, .beta.-thiosulfatoethyl or .beta.-chloroethyl,Z is the .alpha.- or .beta.-bromoacryloyl or .beta.-chloropropionyl or a radical of the formula ##STR4## with B, D and Y of the abovementioned meanings. The novel dyes are suitable for dyeing hydroxyl- and/or carbamoyl-containing material; on hydroxyl-containing material, such as cellulose fibers, they become fixed not only in the alkaline but also in the weakly acid to neutral range, so that they can be used together with disperse dyes for dyeing blend material composed of cellulose and polyester fibers by the dyeing methods for disperse dyes.
Abstract:
Triphendioxazine compounds, which are suitable as fiber-reactive dyestuffs, of the general formula (1) ##STR1## in which R.sup.1 and R.sup.2 are each a hydrogen atom, an optionally substituted alkyl group with 1 to 8 carbon atoms, the substituents being, for example, sulfo, sulfato, carboxy and optionally substituted alkylamino and dialkylamino groups, or a cycloalkyl group which can optionally be substituted by methyl and/or amino, alkanoylamino or benzoylamino, or an optionally substituted phenyl radical, the substituents of which are, for example, sulfo, carboxy, halogen, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, nitro and .beta.-sulfatoethylsulfonyl, or a naphthyl radical which can be substituted by 1, 2 or 3 sulfo groups and/or a fiber-reactive group of the vinylsulfone series, or in which R.sup.1 and R.sup.2, together with the nitrogen atom, can form a heterocyclic radical, and in which the benzene nuclei A can be substituted by 1 or 2 substituents from the group comprising alkyl with 1 to 6 carbon atoms, alkoxy with 1 to 5 carbon atoms, halogen, carboxyl and sulfo, the two radicals X.sup.1 and X.sup.2 are identical to one another or different from one another and are a hydrogen atom, a halogen atom, a cycloalkyl group, an aralkoxy group, an alkoxy group, an aryloxy group, an alkyl group, an aryl group, an aralkyl group or a cyano, carboxy, carbalkoxy, mono- or di-alkylcarbamoyl, arylarylcarbamoyl, alkanoylamino or aroylamino group, and Y represents the vinyl group or ethyl group which contains, in the .beta.-position, a substituent which can be eliminated by an alkali, or is the .beta.-hydroxyethyl group, and M represents a hydrogen atom or an alkali metal or the equivalent of an alkaline earth metal, and the compound (1) contains at least one sulfo or sulfato group.The compounds (1) are used for dyeing material containing hydroxy and/or carboxamide groups, in particular fiber material, such as cellulose fiber material and wool, on which they give deep blue dyeings.
Abstract:
Water-soluble compounds having fiber-reactive dye properties of the general formula ##STR1## in which A is an alkylene of 2 to 6 carbon atoms or a phenylene which can be substituted by 1 or 2 substituents, or is a radical of the formula ##STR2## in which W is a direct bond or a bridge member and the R' and R* each denote hydrogen, chlorine, methyl, methoxy, ethoxy, carboxy or sulfo;B is chlorine or fluorine;R is hydrogen, chlorine, an alkyl of 1 to 4 carbon atoms or an alkoxy of 1 to 4 carbon atoms;M is hydrogen or an alkali metal;n stands for the number zero, 1 or 2,K is a radical of the formula ##STR3## in which D is phenylene which can be substituted by chlorine, bromine, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, carboxy or sulfo, or is naphthalene with optionally 1 or 2 sulfo groups,R.sup.1 denotes hydrogen, chlorine, alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms,R.sup.2 is hydrogen or alkyl of 1 to 4 carbon atoms,G is carboxy, methyl or carbalkoxy of 2 to 5 carbon atoms,Y denotes vinyl, .beta.-sulfatoethyl, .beta.-phosphatoethyl, .beta.-thiosulfatoethyl or .beta.-chloroethyl,Z is the .alpha.- or .beta.-bromoacryloyl or .beta.-chloropropionyl or a radical of the formula ##STR4## with B, D and Y of the abovementioned meanings. The novel dyes are suitable for dyeing hydroxyl- and/or carbamoyl-containing material; on hydroxyl-containing material, such as cellulose fibers, they become fixed not only in the alkaline but also in the weakly acid to neutral range, so that they can be used together with disperse dyes for dyeing blend material composed of cellullose and polyester fibers by the dyeing methods for disperse dyes.
Abstract:
Water-soluble phthalocyanine dyestuffs having vinylsulfonyl or .beta.-substituted ethylsulfonyl groups are prepared by reaction of phthalocyanine sulfonyl chlorides, which may contain sulfo groups, with a primary or secondary amine having vinylsulfonyl or .beta.-substituted ethylsulfonyl groups and, if appropriate, with a second primary or secondary amine of the aliphatic, heterocyclic or aromatic series, in the presence of a pyridinesulfonamide or pyridinecarboxamide.
Abstract:
Water-soluble phthalocyanine compounds of the formula ##STR1## and their salts, wherein Pc is the radical of the metal-free phthalocyanine or of a phthalocyanine containing metals, X means a hydrogen atom, R.sup.1 and R.sup.2 are a hydrogen atom each or a lower, optionally substituted alkyl group, R.sup.1 and R.sup.2 being identical or different from one another, or R.sup.1 and R.sup.2 together with nitrogen atom and an alkylene radical or another heteroatom and two lower alkylene radicals form a heterocyclic ring, a stands for an integer or fractional number of from 1 to 4, b stands for an integer or fractional number from 0 to 3 and c stands for an integer or fractional number from 0 to 3, with a, b and c being identical or different from one another, their sum, however, being from 1 to 4. The novel phthalocyanines can be prepared by reaction of phthalocyanine sulfochlorides optionally containing sulfo-groups with cyanamide or the salts thereof, optionally with another amine of the formula HNR.sup.1 R.sup.2 with R.sup.1 and R.sup.2 having the above-mentioned meaning, in an aqueous medium, an organic solvent or a mixture thereof, and in the presence of an acid-binding agent, optionally under simultaneous or subsequent partial hydrolysis of sulfochloride groups to sulfo groups. The new phthalocyanine compounds are suitable as water-soluble dyestuffs for dyeing and printing fiber materials of wool, silk, linear polyamides, leather and materials containing hydroxy groups: they may generally be applied to these materials in a neutral or acidic aqueous medium, and are subsequently, optionally after an intermediate drying, fixed under heat.
Abstract:
A process for the preparation of water-soluble phthalocyanine dyestuffs containing a fiber-reactive group of the vinylsulfone series, by reacting phthalocyanine sulfochlorides, optionally containing sulfo groups, with a primary or secondary amine which contains a fiber-reactive group of the vinylsulfone series, and optionally with a further primary or secondary amine in common manner, wherein according to the invention a pyridine-sulfonic acid or a pyridine-carboxylic acid is used as catalyst instead of the pyridine, as used previously. The use of pyridine-sulfonic acids or pyridine-carboxylic acids--which results in the same good reaction rate and yield as the use of pyridine in the preparation of phthalocyanine dyestuffs--avoids the considerable drawbacks occurring in the preparation on an industrial scale, which drawbacks are caused by the toxic properties and the unpleasant smell of the pyridine.