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 3-Trifluoromethyl-4-phenyl-pyrazolium azo dyestuffs

Details
Inventors: Coispeau, Gerard Emile Edgard;
Assignee: Produits Chimiques Ugine Kuhlmann (Paris, FR)
Primary Examiner: Higel; Floyd D.
Assistant Examiner:
Attorney, Agent or Firm: Beveridge, Degrandi, Kline & Lunsford

Azopyrazolium dyes of the formula: ##STR1## in which R.sub.1 represents an alkyl group or a phenyl group which may be substituted with a halogen atom or with a nitro, alkoxy or alkyl group, R.sub.2 represents an alkyl group; R.sub.3 represents an atom of hydrogen or halogen; R.sub.4 represents the residue of a coupler R.sub.4 H free of a sulfonic or carboxylic group; and X.sup.- represents a monovalent anion, and 3-trifluoromethyl-4-aryl-5-amino pyrazoles of the formula in which R.sub.3 and R.sub.4 have the same meanings as above and R'.sub.1 represents a hydrogen atom, an alkyl group, or a phenyl group which may be substituted with a halogen atom or with a nitro, alkoxy or alkyl group, are disclosed; methods are disclosed for making these compounds and using them for the dyeing of fibers based on polymers and copolymers of acrylonitrile or on acid-modified polyesters or polyamides to pure and brilliant shades having good fastness, especially fastness to light, e.g., for using the pyrazoles to form the dyes. AZOPYRAZOLIUM DYES, PYRAZOLE COMPOUNDS AND METHODS

DETAILED DESCRIPTION I claim: 1.
A dyestuff of the formula: ##STR8## in which R.
sub.
1 is alkyl containing 1 to 4 carbon atoms, phenyl, chlorophenyl, bromophenyl, nitrophenyl, alkoxy (C.
sub.
1 -C.
sub.
2)-phenyl or alkyl (C.
sub.
1 -C.
sub.
4)-phenyl; R.
sub.
2 is alkyl containing 1 to 4 carbon atoms; R.
sub.
3 is hydrogen, chlorine or bromine; R.
sub.
4 is a radical of the formula: ##STR9## ##STR10## Y.
sub.
1 is hydrogen, methyl, ethyl, cyanoethyl or 2-hydroxypropyl; Y.
sub.
2 is hydrogen, methyl, isopropyl or phenyl; Y.
sub.
3 is hydrogen, phenyl, tolyl, nitrophenyl, chlorophenyl or methoxyphenyl; Z.
sub.
1 is hydrogen, chlorine, methyl, methoxy, ethoxy or acetylamino; Z.
sub.
2 is hydrogen, methyl or ethoxy; Z.
sub.
3 is methyl or ethyl; Z.
sub.
4 is methyl, ethyl, cyanoethyl, trifluoroethyl, diethylaminoethyl, succinimidoethyl or phenyl; and X.
sup.
.
crclbar.
is a monovalent anion.
2.
A dyestuff of the formula: ##STR11## in which R.
sub.
1 is alkyl containing 1 to 4 carbon atoms, phenyl, chlorophenyl, bromophenyl, nitrophenyl, alkoxy (C.
sub.
1 -C.
sub.
2)-phenyl or alkyl (C.
sub.
1 -C.
sub.
4)-phenyl; R.
sub.
2 is alkyl containing 1 to 4 carbon atoms; R.
sub.
3 is hydrogen, chlorine or bromine; R.
sub.
4 is 4-diemethylamino-phenyl, 4-diethylamino-2-methyl-phenyl, 4-diethylamino-2-methoxy-phenyl, 4-(N-ethyl-N-cyanoethylamino)-phenyl, 2-acetylamino-4-diethylamino-phenyl, 2,5-diethoxy-4-diethylamino-phenyl, 2,5-dimethyl-4-dimethylamino-phenyl, 4-[N-2-diethylaminoethyl)-N-ethylamino]-2-methyl-phenyl, 2-methyl-4-(N-trifluoroethyl-N-ethylamino)-phenyl, 2-methyl-4-(N-ethyl-N-succinimidoethylamino)-phenyl, 2-chloro-4-diethylamino-phenyl, 4-(N-ethyl-N-cyanoethylamino)-2-methyl-phenyl, 4-morpholino-phenyl, 4-(N-methyl-N-phenylamino)-phenyl, 4-(4-methoxy-anilino)-1-naphtyl, 3-indolyl, 2-methyl-3-indolyl, 2-phenyl-3-indolyl, 1-methyl-2-phenyl-3-indolyl, 1-ethyl-2-methyl-3-indolyl, 1-cyanoethyl-2-methyl-3-indolyl, 1-cyanoethyl-2-phenyl-3-indolyl, 2-isopropyl-3-indolyl, 1-(2-hydroxypropyl)-2-phenyl-3-indolyl, 3-methyl-5-hydroxy-4-pyrazolyl, 1-phenyl-3-methyl-5-hydroxy-4-pyrazolyl, 1-p-tolyl-3-methyl-5-hydroxy-4-pyrazolyl, 1-m-nitrophenyl-3-methyl-5-hydroxy-4-pyrazolyl, 1-p-chlorophenyl-3-methyl-5-hydroxy-4-pyrazolyl, or 1-p-methoxyphenyl-3-methyl-5-hydroxy-4-pyrazolyl, and X



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