Sumitomo Chemical Company, Limited

Research Association of Dyestuff Manufacturers

Akira Takeshita

Takashi Omura

Naoki Harada

Yutaka Kayane

Tetsuya Miyamoto

Hirokazu Sawamoto

Katsumasa Otake

Makoto Hattori

Shinzaburo Masaki

Masao Nishikuri

Akihiro Taguma

Mikoto Takahashi

Toshihiko Morimitsu

Hirohito Kenmochi

Kiyoteru Kojima

Takeo Fujii

Tooru Tokumaru

Kaneo Yokoyama

Akira Murakami

Osamu Maruyama

Kiyoyasu Hashimoto

Akira Murata

Toshio Nakamatzu

Method of treating a hydroperoxide mixture containing both a primary and tertiary aromatic hydroperoxide, by treating the mixture with an alkali and an organic quaternary ammonium salt. This treatment selectively reduces the content of the primary hydroperoxide in the mixture.

Treatment of hydroperoxide mixture

Process for producing hydroxy-containing alkylated aromatic compounds by the liquid phase reaction of an aromatic compound having at least one hydroxyl group with an alkylating agent in the presence of a heteropoly acid and water.

Method for producing hydroxy-containing alkylated aromatic compounds

A monoazo compound, or a salt thereof, represented by the formula, ##STR1## wherein D is a sulfophenyl group substituted with a methyl, ethyl, methoxy, ethoxy, phenoxy, acetylamino, pripionylamino, benzoylamino, carboxybenzoylamino, maleinylamino or succinylamino group, a naphthyl group substituted with two or three sulfo groups of a group of the formula ##STR2## any one of X.sub.1 or X.sub.2 is a sulfo group and the other is a methoxy or ethoxy group, Y is a fluorine or chlorine atom or an arylamino group substituted with one or two sulfo groups, R is a hydrogen atom or an unsubstituted or substituted lower alkyl group, A is an unsubstituted or substitued phenylene or naphthylene group, and Z is --SO.sub.2 CH.dbd.CH.sub.2 or --SO.sub.2 CH.sub..sub.2 CH.sub.2 Z.sub.1 in which Z.sub.1 is a group capable of being split by the action of an alkali, which is useful as a fiber-reactive dye for dyeing materials in a greenish yellow color excellent in various fastness properties.

Fiber reactive yellow dye of acetoacetonilide having vinyl sulfone-type

A monoazo compound, or a salt thereof, of the formula, ##STR1## wherein W is a hydrogen atom or a carbamoyl group, R.sub.1 is a lower alkyl group, R.sub.2 and R.sub.3 are independently a hydrogen atom or a lower alkyl group, A is an unsubstituted or substituted phenylene or naphthylene group, Y is --SO.sub.2 CH.dbd.CH.sub.2 or --SO.sub.2 CH.sub.2 CH.sub.2 Z, in which Z is a group capable of being split by the action of an alkali, and X is an aromatic or aliphatic group substituted with one or two members selected from sulfonic acid group and carboxylic acid group, which is useful for dyeing fiber materials to give dyed products of a characteristic yellow color excellent in various fastness properties.

Pyridone monoazo compound having vinylsulfone type fiber-reactive group

A phthalocyanine compound represented by the following formula, ##STR1## wherein Pc is a metal-containing or metal-free phthalocyanine residue, R.sup.1 is a hydrogen atom or substituted or unsubstituted lower alkyl group, A is a substituted or unsubstituted phenylene or naphthylene group, Y is --SO.sub.2 CH.dbd.CH.sub.2 or --SO.sub.2 CH.sub.2 CH.sub.2 Z, in which Z is a splittable group by the action of an alkali, W is a bridging group of the following formula, ##STR2## in which R.sup.2 and R.sup.3 are independently a hydrogen atom or a methyl or ethyl group, and n is an integer of from 2 through 6, X is a halogen atom, a is 0 or a number of not more than 2 (0.ltoreq.a.ltoreq.2), and b and c are independently a number of 1 through 3 (1.ltoreq.b.ltoreq.3, 1.ltoreq.c.ltoreq.3), provided that the total of a, b and c is not more than 4 (a+b+c.ltoreq.4), which is useful for dyeing or printing materials, particularly cellulose fiber materials, in a brilliant turquoise blue color excellent in various fastness properties.

Fiber-reactive phthalocyanine compound having both vinylsulfone type and

A compound, or a salt thereof, represented by the formula, ##STR1## wherein X is a halogen atom, Y is a group of --SO.sub.2 CH.dbd.CH.sub.2 or --SO.sub.2 CH.sub.2 CH.sub.2 Z (in which Z is a group capable of being split by the action of an alkali), A is an unsubstituted or substituted phenylene or naphthylene group, B is a cycloalkylene group of the formula, ##STR2## an arylene group of the formula, ##STR3## or an alkylene of the formula --(CH.sub.2).sub.1 --, (in which R.sub.3 and R.sub.4 are independently a hydrogen atom or a methyl, ethyl or methoxy group, n is 0, 1 or 2 and 1 is an integer of 2 to 6), R.sub.1 and R.sub.2 are independently a hydrogen atom or an unsubstituted or substituted lower alkyl group, and m is 0, 1 or 2, provided that the group Y is located at m- or p-position to the group ##STR4## when B is the arylene group, which is useful for dyeing fiber materials, particularly cellulose fiber materials, in a blue color having excellent fastness, with excellent build-up and level-dyeing properties.

Anthraquinone compound having both monohalogenotriazinyl and

A compound of the formula, ##STR1## wherein D is an organic dye moiety, R.sub.1 and R.sub.2 are independently hydrogen or a substituted or unsubstituted lower alkyl group, R.sub.3 is hydrogen or a substituted or unsubstituted lower alkyl, phenyl or naphthyl group, X.sub.1 and X.sub.2 are independently hydrogen, halogen or a lower alkyl, cyano, carbamoyl, vinyl, .beta.-hydroxyethyl, .beta.-sulfoethyl, .beta.-sulfatoethyl, carboxyl, carboxylic acid ester or sulfonic acid group, and Z is appended to the above-defined D or R.sub.3 and stands for --SO.sub.2 CH.dbd.CH.sub.2 or --SO.sub.2 CH.sub.2 CH.sub.2 Y, in which Y is a group capable of being split by the action of an alkali, which is useful for dyeing hydroxyl or amido group-containing fiber materials with excellent build-up properties, thereby giving dyed products having excellent various fastness properties.

Organic dye compound having both pyridiniotriazinyl and vinylsulfone

A pyridone compound of the following formula, or a salt thereof, ##STR1## wherein R.sub.1 and R.sub.2 are independently a hydrogen atom or a lower alkyl group having up to 4 carbon atoms, X is a hydrogen atom or a methyl or sulfo group, A is an unsubstituted or substituted phenylene or naphthylene group, and Y is --SO.sub.2 CH.dbd.CH.sub.2 or --SO.sub.2 CH.sub.2 CH.sub.2 Z, in which Z is a group capable of being split by the action of an alkali. The compound is useful for dyeing or printing fiber materials to give a dyed product of a brilliant yellow color excellent in various fastness properties with good reproducibility.

4-methyl-pyridone monoazo compound having both monochlorotriazinyl and

A compound which is represented by a free acid of the following formula, ##STR1## wherein X is hydrogen, halogen, alkyl or cyano, R.sub.1, R.sub.2 and R.sub.3 are independently hydrogen or alkyl, R.sub.4 is alkyl, W is alkylene, cycloalkylene or arylene, Q is --SO.sub.2 CH.dbd.CH.sub.2 or --SO.sub.2 CH.sub.2 CH.sub.2 L in which L is a group capable of being splitted by the action of an alkali, D is a benzene or naphthalene ring, l and m are independently a number of not less than 0 but not more than 3, and n is a number of more than 0 but not more than 3, provided that l, m and n satisfy 0&lt;l+m+n.ltoreq.4, and which is useful for dyeing fiber materials a blue color with a good build-up property to give a dyed product having excellent fastness properties.

Dioxazine fiber reactive compound

A monoazo compound of the formula, ##STR1## wherein X is hydrogen atom or lower alkyl group; Z is hydrogen atom, halogen atom, alkyl group, acylamino group, benzoylamino group or alkylsulfonylamino group; R.sub.1, R.sub.2, R.sub.3 and R.sub.4 independently are hydrogen atom or alkyl group, provided that R.sub.1, R.sub.2, R.sub.3 and R.sub.4 cannot simultaneously be hydrogen atoms; and R.sub.5 is hydrogen atom, alkyl group, substituted alkyl group, alkenyl group, cycloalkyl group, aralkyl group or phenyl group.

Nitrothiazolyl-monoazo-2,2,4-trimethyl-1,2,3,4-tetrahydroquinoline

A process for producing 1,4-diaminoanthraquinone-2,3-disulfonic acid or a salt thereof which comprises reacting a 1,4-diamino-2,3-dihalogenoanthraquinone with a sulfonating agent in an aqueous medium in the presence of at least one of a quaternary ammonium compound and a quaternary phosphonium compound and optionally, in the presence of an inert organic solvent is disclosed. A process for producing 1,4-diamino-2,3-dicyanoanthraquinone which comprises further reacting the thus obtained 1,4-diaminoanthraquinone-2,3-disulfonic acid or salt thereof with a cyanogenation agent is also disclosed.

Process for producing anthraquinone compounds

A monoazo compound which is useful for dyeing or printing fiber materials, particularly cellulose fiber materials in red color, and which is represented by a free acid of the formula, ##STR1## wherein D is a phenyl group substituted with one to three substituents selected from the group consisting of halogen atoms and methyl, ethyl, methoxy, ethoxy, acetylamino, propionylamino, sulfo and carboxyl groups, R is a C.sub.1 to C.sub.4 alkyl group unsubstituted or substituted with a halogen atom or a hydroxyl, cyano, alkyl, alkoxy, carboxyl, carbamoyl, alkoxycarbonyl or sulfo group, A is a phenylene group unsubstituted or substituted with one or two substituents selected from the group consisting of methyl, ethyl, methoxy, ethoxy and sulfo groups and chlorine and bromine atoms, or a naphthylene group unsubstituted or substituted with one sulfo group, and X is --SO.sub.2 CH.dbd.CH.sub.2 or --SO.sub.2 CH.sub.2 CH.sub.2 Y in which Y is a group capable of being split by the action of an alkali.

Monoazo compound having both monochlorotriazinyl and vinylsulfone type

A process for the production of 1,4-diaminoanthraquinone-2-sulfonic acid or a salt thereof is disclosed, comprising reacting 1-amino-4-bromoanthraquinone-2-sulfonic acid or its salt with liquid ammonia in the presence of a copper catalyst wherein the reaction is carried out in the presence of an inert organic solvent, e.g., n-heptane and cyclohexane. In this process, crystals of the desired product do not substantially deposit on reactor walls, and distillation recovery of ammonia can be performed easily without causing deterioration of the desired product. 1,4-Diaminoanthraquinone-2-sulfonic acid or salt thereof is a useful intermediate for the preparation of, e.g., anthraquinone dyes.

Process for producing 1,4-diaminoanthraquinone-2-sulfonic acid

A phthalocyanine compound which is represented by a free acid of the following formula, ##STR1## wherein Pc is a metal-free or metal-containing phthalocyanine residue, W is a group of ##STR2## in which R' and R' are independently a hydrogen atom or a methyl or ethyl group, and n is an integer of from 2 to 6, R is an unsubstituted or substituted lower alkyl group, A is an unsubstituted or substituted phenylene or naphthylene group, Y is a group of --SO.sub.2 CH.dbd.CH.sub.2 or --SO.sub.2 CH.sub.2 CH.sub.2 Z in which Z is a group capable of being split by the action of an alkali, a is a positive number of from 1 to 3, and b and c are independently a positive number of from 0 to 3, provided that a, b and c statisfy 0&lt;a+b+c.ltoreq.4, and which is useful for dyeing or printing fiber materials, particularly cellulose fiber materials, to give a dyed or printed product of a brilliant turquoise blue color excellent in various fastness, particularly light fastness and wet fastness.

Phthalocyanine fiber reactive compound

In a process for producing an anthraquinone dye intermediate, 1,4-diamino-2,3-dicyanoanthraquinone, by reacting 1,4-diaminoanthraquinone-2-sulfonic acid, a salt thereof, 1,4-diaminoanthraquinone-2-cyanoanthraquinone, 1,4-diamino-2,3-disulfonic acid, or a salt thereof with a cyanogenating agent in an aqueous medium, the yield and quality of the product can be improved markedly by carrying out the reaction in the presence of a quaternary ammonium compound, and further, depending upon the starting material used, in the presence or absence of a dehydrogenating agent.

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Toyonaka, Japan

Akira Takeshita