Patents by Inventor Toshio Hihara
Toshio Hihara has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).
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Patent number: 5332404Abstract: 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.Type: GrantFiled: December 10, 1992Date of Patent: July 26, 1994Assignee: Hoechst Mitsubishi Kasei Co., Ltd.Inventors: Kiyoshi Himeno, Toshio Hihara, Hirotsugu Tsumura, Yoshiharu Hamano
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Patent number: 5290931Abstract: 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.Type: GrantFiled: September 4, 1992Date of Patent: March 1, 1994Assignee: Hoechst Mitsubishi Kasei Co., Ltd.Inventors: Kiyoshi Himeno, Toshio Hihara
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Patent number: 4988801Abstract: A water-soluble monoazo colorant represented by formula (I) in a form of a free acid: ##STR1## wherein D represents ##STR2## (wherein W.sup.2 represents lower alkoxy; U represents lower alkyl or lower alkoxy; Z represents --CH.dbd.CH.sub.2 or --CH.sub.2 CH.sub.2 OSO.sub.3 H and p and q represent each 0 or 1);W.sup.1 represents lower alkoxy; andV represents ##STR3## (wherein X represents halogen; Y represents halogen, sulfo, --OR.sup.1 wherein R.sup.1 represents lower alkyl or lower alkyl substituted by hydroxy, carboxy or sulfo, --O--R.sup.2 O).sub.m R.sup.3 alkyl and m is an integer of 1 to 6, or aliphatic or aromatic amino each substituted by one or two sulfo or carboxy groups);as well as a dyeing process by using the same. These colorants are useful in the dyeing of fibers. These colorants are useful in the dyeing of fibers.Type: GrantFiled: December 20, 1989Date of Patent: January 29, 1991Assignee: Mitsubishi Kasei CorporationInventors: Toshio Hihara, Kanzi Shimizu, Yukiharu Shimizu
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Patent number: 4985545Abstract: A water-soluble formazan colorant, which is represented by the following general formula (I) in the form of free acid: ##STR1## (where: R represents a hydrogen atom or a lower alkyl group which may be substituted; X denotes a phenylene group or a naphthylene group which may be substituted; Y indicates --SO.sub.2 CH.dbd.CH.sub.2 group or --SO.sub.2 C.sub.2 H.sub.4 W group wherein W represents a group to be eliminated by the action of alkali; and Z designates a lower alkylamino group, a phenylamino group or a naphthylamino group, having one or two water-soluble groups selected from the group consisting of hydroxyl group, sulfonic acid group and carboxylic acid group); and a method of dyeing by use of the colorant. The colorant is used to dye cellulosic and nitrogen-containing fibers in blue shades with excellent reactive fixing properties.Type: GrantFiled: August 15, 1988Date of Patent: January 15, 1991Assignee: Mitsubishi Kasei CorporationInventors: Kiyoshi Himeno, Toshio Hihara, Kanzi Shimizu, Yukiharu Shimizu
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Patent number: 4960871Abstract: Monoazo colorants represented by the general formula (I): ##STR1## wherein: D represents ##STR2## (wherein X represents a hydrogen atom or a halogen atom, and Y represents a nitro group, a lower alkylsulfonyl group, a thiocyanic acid group or a halogen atom), or ##STR3## (wherein P represents a nitro group or a lower alkylsulfonyl group, and Q and T each represents a hydrogen atom, a halogen atom or a cyano group);R.sup.1 and R.sup.2 each represents an ethylene group or a propylene group;R.sup.3 and R.sup.4 each represents a hydrogen atom or an alkyl group which may be substituted by a lower alkoxy group or a lower alkoxyalkoxy group; andZ represents a halogen atom.This monoazo colorants include a reactive type pyridine-based monoazo dye suitable for use in dyeing of cellulose or cellulose/polyester mixed fibers in red to orange.Type: GrantFiled: February 17, 1989Date of Patent: October 2, 1990Assignee: Mitsubishi Chemical Industries Inc.Inventors: Toshio Hihara, Yukiharu Shimizu
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Patent number: 4888028Abstract: A water-soluble dye mixture comprising a blue anthraquinone reactive dye represented in its free acid form by the formula: ##STR1## wherein X is --CH.dbd.CH.sub.2 or --C.sub.2 H.sub.4 W wherein W is a group removable by action of alkali and from 0.2 to 5 times by weight to said anthraquinone reactive dye of a blue formazan reactive dye represented in its free acid form by the formula: ##STR2## wherein R is a hydrogen atom or a C.sub.1 -C.sub.4 alkyl group, Y is a halogen atom, --NHC.sub.2 H.sub.4 SO.sub.3 H or ##STR3## and X is --CH.dbd.CH.sub.2 or --C.sub.2 H.sub.4 W wherein W is a group removable by action of alkali.Type: GrantFiled: June 15, 1988Date of Patent: December 19, 1989Assignee: Mitsubishi Kasei CorporationInventors: Toshio Hihara, Riyouichi Sekioka
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Patent number: 4872881Abstract: A dye mixture and a method of dyeing cellulosic fibers by use of the dye mixture, the dye mixture being capable of dyeing the cellulosic fibers favorably even in the presence of a small amount of an inorganic salt at dyeing, and being composed of a blend of a red water-soluble reactive dye to be represented by the following general formula (I) in the form of free acid, and a specific yellow and/or blue water-soluble reactive dye: ##STR1## (where: each of R.sup.1 and R.sup.2 denotes a hydrogen atom or a lower alkyl group which may contain therein a substituent; R.sup.3 represents a hydrogen atom, a lower alkyl group or a halogen atom and X designates --CH.dbd.CH.sub.2 or --C.sub.2 H.sub.4 OSO.sub.3 H).Type: GrantFiled: October 31, 1988Date of Patent: October 10, 1989Assignee: Mitsubishi Kasei CorporationInventors: Takashi Fujita, Toshio Hihara, Yoshio Kogure, Riyouichi Sekioka, Noboru Nakamura
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Patent number: 4843150Abstract: A water soluble disazo colorant represented by formula (I) in the form of free acid: ##STR1## wherein K represents ##STR2## [wherein A represents a methyl group or a carboxylic group; R.sup.2 represents a hydrogen atom, an alkyl group of 1 to 8 carbon atoms, a sulfoalkyl grouop of 1 to 4 carbon atoms, or an alkyl group of 1 to 4 carbon atoms which is substituted by an alkoxy group of 1 to 4 carbon atoms;R.sup.3 represents a hydrogen atom, a halogen atom, a cyano group, a --CONH.sub.2 group, a carboxyl group, a sulfonic group, or a sulfomethyl group, p represents an integer of 1 or 2];Z represents a fluorine atom or ##STR3## [wherein R.sup.4 represents a hydrogen atom or an alkyl group of 1 to 4 carbon atoms;R.sup.5 and R.sup.6 each represents independently a hydrogen atom, an alkyl group of 1 to 4 carbon atoms, an alkoxy group of 1 to 4 carbon atoms, a sulfonic group, or a halogen atom; Y represents --SO.sub.2 CH.dbd.CH.sub.2 or --SO.sub.2 CH.sub.2 CH.sub.Type: GrantFiled: July 9, 1987Date of Patent: June 27, 1989Assignee: Mitsubushi Chemical Industries LimitedInventors: Toshio Hihara, Yukiharu Shimizu, Kanzi Shimizu
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Patent number: 4841029Abstract: A disazo color having three triazine rings, one of which is substituted with a reactive group of --NR.sup.1 --A--SO.sub.2 C.sub.2 H.sub.4 OSO.sub.3 M, wherein R.sup.1 represents a hydrogen atom or a lower alkyl group; A represents a substituted or unsubstituted phenylene or naphthylene group; and M represents a hydrogen atom or an alkali metal. The disazo color is capable of dyeing cellulose-containing fibers under conditions conventionally employed for dyeing polyester fibers with a disperse dye, making it possible to dye mixed fibers of cellulose fiber and polyester fiber in a single-bath through one step.Type: GrantFiled: April 19, 1988Date of Patent: June 20, 1989Assignee: Mitsubishi Chemical Industries LimitedInventors: Yoshiaki Kato, Toshio Hihara
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Patent number: 4837309Abstract: A monoazo dyestuff of the formula: ##STR1## wherein D represents substituted or unsubstituted phenyl, imidazolyl, pyridyl, thiazolyl, thiadiazolyl, thienyl, benzoisothiazolyl, pyridinoisothiazolyl, thienoisothiazolyl, thienothiazolyl or benzothiazolyl, R.sup.1 represents substituted or unsubstituted alkyl, cyclohexyl, alkenyl, aralkyl or aryl, R.sup.2 and R.sup.3 each represents hydrogen, alkyl optionally substituted by cyano, hydroxy, alkoxy or alkoxyalkoxy, alkenyl, cyclohexyl, aryl or aralkyl, or together represent a 5- or 6-membered nitrogen-containing heterocyclic ring formed by combining R.sup.2 and R.sup.3, A represents ##STR2## X represents fluorine or chlorine, and Y.sup.1 represents hydrogen, chlorine, methyl or acylamino. The monoazo dyestuff is especially useful in the dyeing of cellulose-containing fibers and exhibits good fastness properties including good wet color fastness and good light fastness.Type: GrantFiled: February 24, 1984Date of Patent: June 6, 1989Assignee: Mitsubishi Chemical Industries LimitedInventors: Toshio Niwa, Kiyoshi Himeno, Toshio Hihara, Yutaka Kurose, Yukiharu Shimizu
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Patent number: 4801696Abstract: Disazo dyes for dyeing cellulose-containing fibers represented by the following general formula: ##STR1## wherein R.sup.1 and R.sup.2 each represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, a thiocyanato group, a trifluoromethyl group, a formyl group, a lower alkoxycarbonyl group, a lower alkylsulfonyl group, a sulfamoyl group, an N-lower alkylsulfamoyl group or an N,N-di-lower alkylsulfamoyl group, R.sup.3 represents a hydrogen atom, a methyl group, a chlorine atom, a lower alkoxy group or an acylamino group, R.sup.4 represents a hydrogen atom, a methyl group, a chlorine atom or a lower alkoxy group, R.sup.5 represents a hydrogen atom, a lower alkyl group or a halogen atom, --X-- represents ##STR2## --SO.sub.2 -- or --CH.sub.2 --, and n represents 0 or 1. These dyes are capable of dyeing cellulose-containing fibers, particularly fiber blends composed of cellulose fibers and polyester fibers, blue to bluish green with good fastness properties.Type: GrantFiled: June 22, 1987Date of Patent: January 31, 1989Assignee: Mitsubishi Chemical Industries LimitedInventors: Toshio Niwa, Kiyoshi Himeno, Toshio Hihara, Shuichi Maeda
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Patent number: 4743684Abstract: A reactive phthalocyanine dye having a specific substituent capable of dyeing cellulose fibers or a mixed fibers of polyester fibers and cellulose fibers to provide Turkish blue-dyed fibers excellent in color fastness to light and color fastness to washing is disclosed, which is represented by general formula [I] ##STR1##Type: GrantFiled: August 16, 1985Date of Patent: May 10, 1988Assignee: Mitsubishi Chemical IndustriesInventors: Toshio Niwa, Kiyoshi Himeno, Toshio Hihara, Kanzi Shimizu
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Patent number: 4707546Abstract: A reactive monoazo dyestuff of the general formula [I]: ##STR1## wherein R.sup.1 and R.sup.2 each represents substituted or unsubstituted alkyl, cyclohexyl, aralkyl or substituted or unsubstituted aryl, Z represents hydrogen, chlorine, methyl or acylamino, (A) represents substituted or unsubstituted alkylene, (B) represents oxygen or --NH--, X represents fluorine or chlorine, and Y represents --NR.sup.4 R.sup.5 or --OR.sup.6 wherein R.sup.4, R.sup.5 and R.sup.6 each represents hydrogen, substituted or unsubstituted alkyl, alkenyl, cyclohexyl, aryl or aralkyl, or --NR.sup.4 R.sup.5 represents a 5- or 6-membered nitrogen-containing heterocyclic ring formed by combining R.sup.4 and R.sup.5.Type: GrantFiled: January 23, 1986Date of Patent: November 17, 1987Assignee: Mitsubishi Chemical Industries LimitedInventors: Toshio Niwa, Kiyoshi Himeno, Toshio Hihara
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Patent number: 4626590Abstract: Reactive pyridone azo dyestuffs of the general formula [I]: ##STR1## wherein D represents ##STR2## represents phenylene optionally substituted by lower alkyl, lower alkoxy, trifluoromethyl or halogen, ##STR3## represents phenylene optionally substituted by lower alkyl, lower alkoxy, halogen or acetylamino,--A--represents --CH.sub.2 --, --C.sub.2 H.sub.4 --, --OC.sub.2 H.sub.4 --, ##STR4## --SO.sub.2 NHC.sub.2 H.sub.4 --or --SO.sub.2 C.sub.2 H.sub.4 --, --X represents hydrogen, lower alkyl, lower alkoxy, nitro, trifluoromethyl or halogen,--Y represents alkyl, aryl or aralkyl optionally substituted by lower alkoxy or phenoxy,--Z--represents a connecting group of --O--or --S--,--V represents --CN or --CONH.sub.2,--W represents a 6-membered nitrogen-containing heterocyclic ring having at least one active halogen atom, andn represents 0 or 1.These reactive pyridone azo distuffs give dyeings which are yellowish to reddish orange in color which have excellent light fastness.Type: GrantFiled: November 6, 1984Date of Patent: December 2, 1986Assignee: Mitsubishi Chemical Industries LimitedInventors: Toshio Niwa, Kiyoshi Himeno, Toshio Hihara, Yukiharu Shimizu
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Patent number: 4623719Abstract: This invention relates to disazo dyestuffs for cellulose or cellulose-containing fibers represented by the formula: ##STR1## wherein R.sup.1 represents a hydrogen atom, a nitro group, a halogen atom, an alkyl group of 1 or 2 carbon atoms or an acetylamino group; R.sup.2 and R.sup.3 each represents a hydrogen atom, an alkyl group of 1 or 2 carbon atoms, and alkoxy group or an acetylamino group; Y.sup.1 and Y.sup.2 each represents a hydrogen atom or an alkyl group, and alkenyl group, a cyclohexyl group, an aryl group or an aralkyl group which group ma optionally be substituted by cyano, hydroxyl, lower alkoxy or dialkylamino, or NY.sup.1 Y.sup.2 represents a 5-membered or 6-membered nitrogen-containing heretocyclic ring formed by combination of Y.sup.1 and Y.sup.2, and the total carbon atoms in Y.sup.1 and Y.sup.2 is 18 or less.Type: GrantFiled: March 24, 1986Date of Patent: November 18, 1986Assignee: Mitsubishi Chemical Industries LimitedInventors: Toshio Niwa, Kiyoshi Himeno, Toshio Hihara
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Patent number: 4515716Abstract: Diaminopyridine-based azo dyes for cellulose-containing fibers, represented by the following formula: ##STR1## and the other is hydrogen, phenyl, benzyl, allyl, or alkyl which are unsubstituted or substituted by hydroxyl or lower alkoxy(whereinA is methylene, ethylene, propylene, or 1,3-butylene;n is 0 or 1;Y.sup.1 and Y.sup.2, which are the same or different, are hydrogen, alkyl, alkenyl, cyclohexyl, aryl, or aralkyl which are unsubstituted or substituted by cyano, hydroxy, lower alkoxy, or dialkylamino, or Y.sup.1 and Y.sup.2 together form a 5- or 6-membered heterocyclic ring (NY.sup.1 Y.sup.2) containing one nitrogen, the total number of carbon atoms of Y.sup.1 and Y.sup.2 being 18 or less;R.sup.1 is nitro, cyano, methylsulfonyl, phenylsulfonyl, mono-lower alkylaminosulfonyl, di-lower alkylaminosulfonyl, acetyl, or benzoyl;R.sup.2 and R.sup.3, which are the same or different, are hydrogen, trifluoromethyl, halogen, or cyano;R.sup.Type: GrantFiled: September 3, 1982Date of Patent: May 7, 1985Assignee: Mitsubishi Chemical Industries LimitedInventors: Toshio Niwa, Toshio Hihara
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Patent number: 4507476Abstract: This invention relates to an anthraquinone dyestuff for cellulose containing fibers represented by the formula: ##STR1## wherein R.sup.1 represents amino or hydroxyl, R.sup.2 represents hydrogen, chlorine, bromine, cyano or --SO.sub.2 R wherein R represents methyl, ethyl or phenyl, R.sup.3 and R.sup.4 each represents hydrogen, amino, hydroxyl, nitro, chlorine or bromine, Y represents a connecting group consisting of --O-- or --S--, one of X.sup.1 and X.sup.2 is hydrogen and the other is a group of the formula: ##STR2## wherein --Z-- represents a connecting group consisting of --O-- or --S--, --W.sup.1 represents phenyl or --NR.sup.6 R.sup.7, R.sup.5 represents hydrogen, methyl, ethyl, methoxy, ethoxy, chlorine or bromine, R.sup.6 and R.sup.7 each represents hydrogen or alkyl, alkenyl, cyclohexyl, aryl or aralkyl which may optionally be substituted by lower alkoxy, or NR.sup.6 R.sup.7 represents a 5-membered or 6-membered nitrogen-containing heterocyclic ring formed by combination of R.sup.6 and R.sup.Type: GrantFiled: January 5, 1984Date of Patent: March 26, 1985Assignee: Mitsubishi Chemical Industries LimitedInventors: Toshio Niwa, Kiyoshi Himeno, Toshio Hihara
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Patent number: 4500710Abstract: Quinophthalone dyes for cellulose-containing fibers represented by the following general formula: ##STR1## wherein X represents a hydrogen atom, a chlorine atom or a bromine atom, --A-- represents a methylene group, an ethylene group, a propylene group or a 1,3-butylene group, n represents 0 or 1, --Y-- represents a linkage group of --O-- or --S--, R.sup.1 and R.sup.2 each represents a hydrogen atom, an alkyl or alkenyl group which may optionally be substituted with a cyano group, a hydroxy group, a lower alkoxy group or by a dialkylamino group, or R.sup.1 and R.sup.2 may be combined together with the adjacent nitrogen atom to form a 5- or 6-membered, nitrogen-containing heterocyclic ring having the total carbon atom number in R.sup.1 and R.sup.2 of up to 18.Type: GrantFiled: June 16, 1983Date of Patent: February 19, 1985Assignee: Mitsubishi Chemical Industries, LimitedInventors: Toshio Niwa, Toshio Hihara
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Patent number: 4500455Abstract: Diaminopyridine dyes for dyeing cellulose-containing fibers, particularly cellulose fibers and polyester-cellulose fibers in from orange to bluish red, with excellent fastness to light. The dyes are represented by the formula (I): ##STR1## X is a hydrogen atom, or a halogen atom; Y is an alkoxy group containing from 1 to 5 carbon atoms, --O--R.sup.10 --O--R.sup.11, or a phenoxy group; andn is 2 or 3, and wherein R.sup.1 is a nitro group, a cyano group, a methylsulfonyl group, a phenylsulfonyl group, a mono- or di-lower alkylaminosulfonyl group, an acetyl group, or a benzoyl group; R.sup.2 and R.sup.3 are each a hydrogen atom, a trifluoromethyl group, a halogen atom, or a cyano group; R.sup.4 is a hydrogen atom, a lower alkyl group, a mono- or di-lower alkylaminosulfonyl group, a mono- or di-lower alkylcarbamoyl group, or an acetylamino group; R.sup.5 and R.sup.6 are each a hydrogen atom, a halogen atom, or a lower alkyl group; R.sup.7 is a lower alkyl group; R.sup.8 is a hydrogen atom or a halogen atom; R.Type: GrantFiled: July 21, 1982Date of Patent: February 19, 1985Assignee: Mitsubishi Chemical Industries, LimitedInventors: Toshio Niwa, Toshio Hihara, Yukiharu Shimizu
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Patent number: 4473499Abstract: Reactive disazo dyes for dyeing cellulose-containing fibers, represented by the general formula (I): ##STR1## wherein ##STR2## is a phenyl group which may be substituted; Y.sup.1 is a phenyl group which may be substituted; Y.sup.2 is an allyl group, a benzyl group, or an alkyl group which may be substituted; ##STR3## is a phenyl group which may be substituted; and ##STR4## is a phenyl group which may be substituted, ##STR5## is a naphthylene group, or a phenylene group which may be substituted, ##STR6## is a phenylene group which may be substituted, and R.sup.1 and R.sup.2 are each a hydrogen atom, an alkyl group which may be substituted by a cyano group, a hydroxy group, a lower alkoxy group, or a dialkylamino group, or may combine together in combination with N to form a 5- or 6- membered nitrogen-containing heterocyclic ring, the total number of carbon atoms of R.sup.1 and R.sup.2 being 18 or less.Type: GrantFiled: July 20, 1982Date of Patent: September 25, 1984Assignee: Mitsubishi Chemical Industries LimitedInventors: Toshio Niwa, Toshio Hihara