Mitsubishi Chemical Industries Limited

Dystar Japan Ltd.

Mitsubishi Kasei Corporation

Hoechst Mitsubishi Kasei Co., Ltd.

Hoechst Mitsubhishi Kasei Co., Ltd.

Hoeshst Mitsubishi Kasei Co., Ltd.

Toshio Hihara

Kiyoshi Himeno

Toshio Niwa

Yukiharu Shimizu

Kanzi Shimizu

Yousuke Takahashi

Ryouichi Sekioka

Riyouichi Sekioka

Yoshiharu Hamano

Yoshiaki Kato

Shuichi Maeda

Seiichi Imahori

Takao Hirota

Yutaka Kurose

Takashi Fujita

Tomio Yomeyama

Hirotsugu Tsumura

Noboru Nakamura

Wataru Shimizu

Yoshio Kogure

Shinji Kubo

Ryouchi Sekioka

A red reactive dye having the following formula (I) in its free acid form: ##STR1## wherein X is --CH.dbd.CH.sub.2 or --C.sub.2 H.sub.4 W (wherein W is a group splittable by alkali), A is a C.sub.2-3 alkylene group or a C.sub.2-3 alkylenoxy C.sub.2-3 alkylene group, E is a hydrogen atom, a C.sub.1-3 alkyl group or --A--SO.sub.2 X (wherein A and X are as defined above), n is 0 or 1, l is 1 or 2, m is 0 or 1, and R is a hydrogen atom, --OH, --CN, --CH.sub.3, --CF.sub.3, --SO.sub.3 H, --COOH, --CH.sub.2 SO.sub.3 H or --CH.sub.2 SO.sub.2 X (wherein X is as defined above), provided that a compound of the formula (I) wherein R is a hydrogen atom, each of m and n is 0, l is 1, and --SO.sub.2 X is --SO.sub.2 CH.dbd.CH.sub.2 which is bonded at the ortho position to the azo group, is excluded.

Red reactive dyes, their compositions and dyeing method employing them

A blue type disperse dye mixture comprising 1.0 part by weight of at least one dye of the formula (1), from 0 to 0.2 part by weight of at least one dye of the formula (2), from 0.05 to 1.0 part by weight of at least one dye of the formula (3) and from 0.05 to 1.0 part by weight of at least one dye of the formula (4): ##STR1## wherein X is a chlorine atom or a bromine atom, R.sup.1 is a C.sub.1-5 alkyl group, R.sup.2 is a C.sub.1-4 alkyl group, and R.sup.3 is a C.sub.1-5 alkyl group or an allyl group, provided that R.sup.1, R.sup.2 and R.sup.3 may, respectively, be the same or different among the formulae (1) to (4).

Blue type disperse dye mixture and process for its preparation

A blue type disperse dye mixture comprising a monoazo dye of the formula (1) in an amount of 1.0 part by weight and at least one of anthraquinone dyes of the formulae (2) to (4) in a total amount of from 0.2 to 3.0 parts by weight: ##STR1##

Blue type disperse dye mixture

A monoazo dye of the following formula (I): ##STR1## wherein R is phenyl, phenoxy or benzyl, and D is a group of the formula (D1), (D2), (D3) or (D4): ##STR2## wherein each of X.sup.1, X.sup.2 and X.sup.3, which are independent of one another, is hydrogen or chlorine, X.sup.4 is hydrogen, chlorine, methyl or --NHCOR.sup.1, wherein R.sup.1 is C.sub.1-4 alkyl or phenyl; ##STR3## wherein X.sup.4 is as defined above, Y.sup.1 is hydrogen, chlorine or C.sub.1-4 alkoxy; ##STR4## wherein X.sup.5 is hydrogen, halogen, methyl or --NHZ, wherein Z is C.sub.1-4 alkylsurfonyl, C.sub.1-4 alkylcarbonyl, phenylsulfonyl, phenylcarbonyl, C.sub.1-2 alkoxy C.sub.1-2 alkylcarbonyl or aminocarbonyl, Y.sup.2 is hydrogen, methyl or C.sub.1-2 alkoxy, and Q.sup.1 is cyano or C.sub.1-4 alkylcarbonyl; ##STR5## wherein P is formyl, nitro or cyano, Q.sup.2 is cyano or nitro, T is halogen, methyl, phenyl or methylsulfonyl, X.sup.5 is as defined above, and Y.sup.3 is hydrogen or C.sub.1-2 alkoxy.

Benzothiazolemonoazo dyes

A blue disperse dye mixture comprising a monoazo dye of the following formula (1) and at least one azo dye selected from the group consisting of dyes of the following formulas (2), (3), (4) and (5): ##STR1## wherein each of the variables is defined in the specification.

Blue disperse dye mixture

A dye composition containing at least one turquoise blue monoazo dye of the formula (I): ##STR1## and at least one additional dye which is at least one yellow monoazo dye of the formula (II): ##STR2## or at least one blue anthraquinone dye of the formula (III): ##STR3## or at least one navy blue dye of the formula (IV): ##STR4##

Disperse dye compositions

A process for producing a monoazodye of the following formula (III): ##STR1## wherein X.sup.1 is nitro or halogen, X.sup.2 is halogen, R.sup.1 is lower alkoxy, R.sup.2 is lower alkyl, each of R.sup.3 and R.sup.4, which are independent of each other, is alkyl, cyanoalkyl or alkylcarbonyloxyalkyl, and each of m and n, which are independent of each other, is 0 or 1, which comprises diazotizing an aniline derivative of the following formula (I): ##STR2## wherein X.sup.1 and X.sup.2 are as defined above, followed by coupling with an aniline derivative of the following formula (II): ##STR3## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, m and n are as defined above, wherein a reaction mixture obtained by the coupling reaction is heat-treated in the presence of a polyoxyethylene higher fatty acid ester type nonionic surfactant, followed by filtration to obtain said monoazo compound in the form of a cake.

Process for producing a monoazodye by diazo-coupling of a p-nitroanaline

A monoazo dye of the following formula (I): ##STR1## wherein R is phenyl, phenoxy or benzyl, and D is a group of the formula (D1), (D2), (D3) or (D4): ##STR2## wherein each of X.sup.1, X.sup.2 and X.sup.3, which are independent of one another, is hydrogen or chlorine, X.sup.4 is hydrogen, chlorine, methyl or --NHCOR.sup.1, wherein R.sup.1 is C.sub.1-4 alkyl or phenyl; ##STR3## wherein X.sup.4 is as defined above, Y.sup.1 is hydrogen, chlorine or C.sub.1-4 alkoxy; ##STR4## wherein X.sup.5 is hydrogen, halogen, methyl or --NHZ, wherein Z is C.sub.1-4 alkylsulfonyl, C.sub.1-4 alkylcarbonyl, phenylsulfonyl, phenylcarbonyl, C.sub.1-2 alkoxy C.sub.1-2 alkylcarbonyl or aminocarbonyl, Y.sup.2 is hydrogen, methyl or C.sub.1-2 alkoxy, and Q.sup.1 is cyano or C.sub.1-4 alkylcarbonyl; ##STR5## wherein P is formyl, nitro or cyano, Q.sup.2 is cyano or nitro, T is halogen, methyl, phenyl or methylsulfonyl, X.sup.5 is as defined above, and Y.sup.3 is hydrogen or C.sub.1-2 alkoxy. The dyes of the formula (I) are useful for dyeing polyester fibers, particularly fine denier polyester fibers.

Thiophene-type monoazo dyes

A disperse dye mixture comprising dye (I) and dye (II) blended at a ratio of from 0.1 to 10 times by weight of dye (II) to dye (I): ##STR1## wherein X is halogen, nitro, cyano, thiocyanate, methylsulfonyl, C.sub.1 or C.sub.2 alkylcarbonyl, C.sub.1 -C.sub.4 alkoxycarbonyl or vinylsulfonyl, Y is hydrogen, halogen, cyano, trifluoromethyl or methylsulfonyl, W is hydrogen, halogen, C.sub.1 or C.sub.2 alkyl or C.sub.1 or C.sub.2 alkoxy, and each of R.sup.1 and R.sup.2 which are independent of each other, is hydrogen, C.sub.1 --C.sub.8 alkyl, or C.sub.2 -C.sub.4 alkyl substituted by halogen, hydroxyl, cyano, alkoxy, alkoxyalkoxy, a hydroxyalkoxy, hydroxyalkoxyalkoxy, acyloxyalkoxy or acyloxyalkoxyalkoxy, provided that each alkoxy has from 1 to 4 carbon atoms.

Disperse dye mixture

A monoazo disperse dye for dyeing polyester fibers of the following formula (I): ##STR1## wherein one of R.sup.1 and R.sup.2 is ##STR2## wherein W is hydrogen, halogen, C.sub.1 -C.sub.2 alkyl or alkoxy, the other of R.sup.1 and R.sup.2 is C.sub.1 -C.sub.4 alkyl, or C.sub.2 -C.sub.4 alkyl substituted by cyano, halogen, hydroxy, hydroxyalkoxy, C.sub.1 -C.sub.4 alkoxy, hydroxyalkoxyalkoxy, acetoxalkoxy, acyloxyalkoxyalkoxy alkoxyalkoxy, alkoxycarbonyloxy or acetoxy, and Y is hydrogen or halogen.

3-cyano-5-nitrothiophene type monoazo dyes and mixtures thereof

A water-soluble monoazodye having the following formula (I) in its free acid form: ##STR1## wherein X is --CH.dbd.CH.sub.2 or --CH.sub.2 CH.sub.2 W wherein W is a leaving group removable by alkali; R.sup.1 is methyl, --NHCONH.sub.2 or --NHCOT.sup.1 wherein T.sup.1 is methyl, ethyl, --CH.sub.2 CH.sub.2 COOH or --CH.dbd.CHCOOH; R.sup.2 is hydrogen, lower alkyl or lower alkoxy; and Z is ##STR2## wherein P is cyano or halogen, each of Q and U which are independent of each other, is halogen, V is halogen or ##STR3## and Y is halogen or a group of the following formula (1) or (2): ##STR4## wherein R.sup.3, A, R.sup.4 and E are as defined in the disclosure and G is as defined above, has a moderate yellow to orange color and is particularly suitable for dyeing cellulose fibers or nitrogen-containing fibers.

Water-soluble monoazodye containing a triazinyl or pyrimidinyl group and

Water-insoluble naphthalic acid imide dyestuffs of the following formula: ##STR1## wherein D is ##STR2## wherein R.sup.1 is C.sub.1 -C.sub.8 alkyl which may be substituted, R.sup.2 is hydrogen, halogen, lower alkyl, lower alkoxy or cyano, X is oxygen or sulfur, and m is 0 or 1; A is phenylene, alkylene, aralkylene or --C.sub.2 H.sub.4 OC.sub.2 H.sub.4 --; B is oxygen, sulfur or ##STR3## wherein R.sup.3 is hydrogen or lower alkyl; Y is a 6-membered nitrogen-containing heterocyclic ring having at least one active halogen atom; and n is 0 or 1.

Method of dyeing a fiber mixture with water-insoluble naphthalic acid

A disperse dye mixture comprising a monoazo dye of the following formula (1) and a monoazo dye of the following formula (2) blended thereto in an amount of from 0.1 to 10 times by weight of the dye of the formula (1): ##STR1## wherein each of X.sup.1 and X.sup.2 which are independent of each other, is nitro, cyano, sulfomethyl or halogen, each of Y.sup.1, Y.sup.2, Z.sup.1 and Z.sup.2 which are independent of one another, is hydrogen, cyano, nitro, trifluoromethyl, halogen or sulfomethyl, each of W.sup.1 and W.sup.2 which are independent of each other, is hydrogen, halogen, C.sub.1 -C.sub.2 alkyl or alkoxy, and each of R.sup.1 and R.sup.2 which are independent of each other, is C.sub.1 -C.sub.4 alkyl, or C.sub.2 -C.sub.4 alkyl which is substituted by cyano, halogen, hydroxy, hydroxyalkoxy, C.sub.1 -C.sub.4 alkyl, hydroxyalkoxyalkoxy, acyloxyalkoxy, acyloxyalkoxyalkoxy or alkoxyalkoxy.

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Kitakyushu, Japan

Toshio Hihara