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: 7824451Abstract: The present invention provides a blue dye mixture which contains the pigments represented by formulae [1], [2], [3], and [4] The present invention also relates to dye mixtures in which there are compounded therewith a yellow dye mixture and/or a red dye mixture. The invention further relates to a method of dyeing polyester-based fibers and dyed polyester-based fibers and dyed polyester-based fiber materials.Type: GrantFiled: June 29, 2004Date of Patent: November 2, 2010Assignee: DyStar Textilfarben GmbH & Co. Deutschland KGInventors: Toshio Hihara, Wataru Seto, Koichi Fujisaki, Daisuke Hosoda, Hiroshi Inoue
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Publication number: 20070271710Abstract: The present invention relates to the use of a yellow and/or a red and/or a blue component of disperse dyes for dyeing poly(lactic acid) fibers or poly(lactic acid) based fibers.Type: ApplicationFiled: June 17, 2005Publication date: November 29, 2007Applicant: DyStar Textifarben GmbH & Co. Deutschland KGInventors: Daisuke Hosoda, Koichi Fujisaki, Toshio Hihara
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Publication number: 20060230549Abstract: The present invention provides a blue dye mixture which contains the pigments represented by formulae [1], [2], [3], and [4] The present invention also relates to dye mixtures in which there are compounded therewith a yellow dye mixture and/or a red dye mixture. The invention further relates to a method of dyeing polyester-based fibers and dyed polyester-based fibers and dyed polyester-based fiber materials.Type: ApplicationFiled: June 29, 2004Publication date: October 19, 2006Applicant: DyStar Textilfarben GmbH & Co. Deutschland KGInventors: Toshio Hihara, Wataru Seto, Koichi Fujisaki, Daisuke Hosoda, Hiroshi Inoue
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Patent number: 7097670Abstract: The present inventions refers to a dye mixture comprising from 25 to 80% by weight with respect to the total dyestuff fraction of the yellow dyestuff represented by the structural formula [1] and from 75 to 20% by weight with respect to the total dyestuff fraction of a yellow dyestuff represented by the structural formula [2] wherein R denotes a C1 to C4 hydroxyalkyl group.Type: GrantFiled: August 2, 2003Date of Patent: August 29, 2006Assignee: DyStar Textilfarben GmbH & Co. Deutschland KGInventors: Toshio Hihara, Hiroshi Inoue, Wataru Seto
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Publication number: 20050272920Abstract: The present inventions refers to a dye mixture comprising from 25 to 80% by weight with respect to the total dyestuff fraction of the yellow dyestuff represented by the structural formula [1] and from 75 to 20% by weight with respect to the total dyestuff fraction of a yellow dyestuff represented by the structural formula [2] wherein R denotes a C1 to C4 hydroxyalkyl group.Type: ApplicationFiled: August 2, 2003Publication date: December 8, 2005Applicant: DYSTAR TEXITILFARBEN GMBH & CO.Inventors: Toshio Hihara, Hiroshi Inoue, Wataru Seto
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Patent number: 6388057Abstract: A water-insoluble monoazo dye represented by the following structural formula [I] having a crystal modification characterized by an X-ray diffraction pattern (CuK&agr;) showing one strong peak at a diffraction angle (2&thgr;) of 11.1±0.1° and also four intermediate peaks at 8.1±0.1°, 21.8±0.1°, 23.1±0.1° and 25.2±0.1°.Type: GrantFiled: August 31, 2001Date of Patent: May 14, 2002Assignee: DyStar Textilfarben GmbH & Co. Deutschland KGInventors: Toshio Hihara, Hiroshi Inoue, Yousuke Takahashi
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Patent number: 5756690Abstract: 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.Type: GrantFiled: April 25, 1996Date of Patent: May 26, 1998Assignee: DyStar Japan Ltd.Inventors: Toshio Hihara, Yousuke Takahashi
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Patent number: 5744588Abstract: 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).Type: GrantFiled: October 9, 1996Date of Patent: April 28, 1998Assignee: DyStar Japan Ltd.Inventors: Kiyoshi Himeno, Toshio Hihara, Yousuke Takahashi
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Patent number: 5734028Abstract: 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.Type: GrantFiled: October 18, 1996Date of Patent: March 31, 1998Assignee: DyStar Japan Ltd.Inventors: Kiyoshi Himeno, Toshio Hihara, Ryouchi Sekioka
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Patent number: 5608042Abstract: 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.Type: GrantFiled: January 31, 1996Date of Patent: March 4, 1997Assignee: Dystar Japan Ltd.Inventors: Kiyoshi Himeno, Toshio Hihara, Ryouichi Sekioka
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Patent number: 5595575Abstract: 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.Type: GrantFiled: November 8, 1995Date of Patent: January 21, 1997Assignee: DyStar Japan Ltd.Inventors: Kiyoshi Himeno, Toshio Hihara, Ryouichi Sekioka
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Patent number: 5569309Abstract: 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##Type: GrantFiled: May 19, 1995Date of Patent: October 29, 1996Assignee: Dystar Japan Ltd.Inventors: Toshio Hihara, Kiyoshi Himeno
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Patent number: 5545236Abstract: 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.Type: GrantFiled: March 9, 1995Date of Patent: August 13, 1996Assignee: DyStar Japan Ltd.Inventors: Toshio Hihara, Yousuke Takahashi
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Patent number: 5532344Abstract: 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.Type: GrantFiled: March 29, 1993Date of Patent: July 2, 1996Assignee: Dystar Japan Ltd.Inventors: Kiyoshi Himeno, Toshio Hihara, Yoshiharu Hamano, Shinji Kubo
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Patent number: 5527888Abstract: 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.Type: GrantFiled: March 7, 1995Date of Patent: June 18, 1996Assignee: Dystar Japan Ltd.Inventors: Kiyoshi Himeno, Toshio Hihara, Ryouichi Sekioka
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Patent number: 5494493Abstract: 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.Type: GrantFiled: November 22, 1994Date of Patent: February 27, 1996Assignee: Dystar Japan Ltd.Inventors: Kiyoshi Himeno, Toshio Hihara
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Patent number: 5440024Abstract: 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.Type: GrantFiled: July 13, 1993Date of Patent: August 8, 1995Assignee: Hoechst Mitsubishi Kasei Co., Ltd.Inventors: Kiyoshi Himeno, Toshio Hihara, Wataru Shimizu
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Patent number: 5380827Abstract: 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.Type: GrantFiled: April 20, 1993Date of Patent: January 10, 1995Assignee: Hoeshst Mitsubishi Kasei Co., Ltd.Inventors: Yousuke Takahashi, Yukiharu Shimizu, Toshio Hihara, Kiyoshi Himeno
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Patent number: 5368612Abstract: 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: August 2, 1993Date of Patent: November 29, 1994Assignee: Hoechst Mitsubhishi Kasei Co., Ltd.Inventors: Kiyoshi Himeno, Toshio Hihara
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Patent number: RE37004Abstract: 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.Type: GrantFiled: August 22, 1997Date of Patent: December 26, 2000Assignee: Dystar Japan Ltd.Inventors: Yousuke Takahashi, Yukihara Shimizu, Toshio Hihara, Kiyoshi Himeno