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).

  • Patent number: 7824451
    Abstract: 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: Grant
    Filed: June 29, 2004
    Date of Patent: November 2, 2010
    Assignee: DyStar Textilfarben GmbH & Co. Deutschland KG
    Inventors: Toshio Hihara, Wataru Seto, Koichi Fujisaki, Daisuke Hosoda, Hiroshi Inoue
  • Publication number: 20070271710
    Abstract: 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: Application
    Filed: June 17, 2005
    Publication date: November 29, 2007
    Applicant: DyStar Textifarben GmbH & Co. Deutschland KG
    Inventors: Daisuke Hosoda, Koichi Fujisaki, Toshio Hihara
  • Publication number: 20060230549
    Abstract: 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: Application
    Filed: June 29, 2004
    Publication date: October 19, 2006
    Applicant: DyStar Textilfarben GmbH & Co. Deutschland KG
    Inventors: Toshio Hihara, Wataru Seto, Koichi Fujisaki, Daisuke Hosoda, Hiroshi Inoue
  • Patent number: 7097670
    Abstract: 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: Grant
    Filed: August 2, 2003
    Date of Patent: August 29, 2006
    Assignee: DyStar Textilfarben GmbH & Co. Deutschland KG
    Inventors: Toshio Hihara, Hiroshi Inoue, Wataru Seto
  • Publication number: 20050272920
    Abstract: 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: Application
    Filed: August 2, 2003
    Publication date: December 8, 2005
    Applicant: DYSTAR TEXITILFARBEN GMBH & CO.
    Inventors: Toshio Hihara, Hiroshi Inoue, Wataru Seto
  • Patent number: 6388057
    Abstract: 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: Grant
    Filed: August 31, 2001
    Date of Patent: May 14, 2002
    Assignee: DyStar Textilfarben GmbH & Co. Deutschland KG
    Inventors: Toshio Hihara, Hiroshi Inoue, Yousuke Takahashi
  • Patent number: 5756690
    Abstract: 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: Grant
    Filed: April 25, 1996
    Date of Patent: May 26, 1998
    Assignee: DyStar Japan Ltd.
    Inventors: Toshio Hihara, Yousuke Takahashi
  • Patent number: 5744588
    Abstract: 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: Grant
    Filed: October 9, 1996
    Date of Patent: April 28, 1998
    Assignee: DyStar Japan Ltd.
    Inventors: Kiyoshi Himeno, Toshio Hihara, Yousuke Takahashi
  • Patent number: 5734028
    Abstract: 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: Grant
    Filed: October 18, 1996
    Date of Patent: March 31, 1998
    Assignee: DyStar Japan Ltd.
    Inventors: Kiyoshi Himeno, Toshio Hihara, Ryouchi Sekioka
  • Patent number: 5608042
    Abstract: 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: Grant
    Filed: January 31, 1996
    Date of Patent: March 4, 1997
    Assignee: Dystar Japan Ltd.
    Inventors: Kiyoshi Himeno, Toshio Hihara, Ryouichi Sekioka
  • Patent number: 5595575
    Abstract: 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: Grant
    Filed: November 8, 1995
    Date of Patent: January 21, 1997
    Assignee: DyStar Japan Ltd.
    Inventors: Kiyoshi Himeno, Toshio Hihara, Ryouichi Sekioka
  • Patent number: 5569309
    Abstract: 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: Grant
    Filed: May 19, 1995
    Date of Patent: October 29, 1996
    Assignee: Dystar Japan Ltd.
    Inventors: Toshio Hihara, Kiyoshi Himeno
  • Patent number: 5545236
    Abstract: 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: Grant
    Filed: March 9, 1995
    Date of Patent: August 13, 1996
    Assignee: DyStar Japan Ltd.
    Inventors: Toshio Hihara, Yousuke Takahashi
  • Patent number: 5532344
    Abstract: 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: Grant
    Filed: March 29, 1993
    Date of Patent: July 2, 1996
    Assignee: Dystar Japan Ltd.
    Inventors: Kiyoshi Himeno, Toshio Hihara, Yoshiharu Hamano, Shinji Kubo
  • Patent number: 5527888
    Abstract: 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: Grant
    Filed: March 7, 1995
    Date of Patent: June 18, 1996
    Assignee: Dystar Japan Ltd.
    Inventors: Kiyoshi Himeno, Toshio Hihara, Ryouichi Sekioka
  • Patent number: 5494493
    Abstract: 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: Grant
    Filed: November 22, 1994
    Date of Patent: February 27, 1996
    Assignee: Dystar Japan Ltd.
    Inventors: Kiyoshi Himeno, Toshio Hihara
  • Patent number: 5440024
    Abstract: 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: Grant
    Filed: July 13, 1993
    Date of Patent: August 8, 1995
    Assignee: Hoechst Mitsubishi Kasei Co., Ltd.
    Inventors: Kiyoshi Himeno, Toshio Hihara, Wataru Shimizu
  • Patent number: 5380827
    Abstract: 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: Grant
    Filed: April 20, 1993
    Date of Patent: January 10, 1995
    Assignee: Hoeshst Mitsubishi Kasei Co., Ltd.
    Inventors: Yousuke Takahashi, Yukiharu Shimizu, Toshio Hihara, Kiyoshi Himeno
  • Patent number: 5368612
    Abstract: 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: Grant
    Filed: August 2, 1993
    Date of Patent: November 29, 1994
    Assignee: Hoechst Mitsubhishi Kasei Co., Ltd.
    Inventors: Kiyoshi Himeno, Toshio Hihara
  • Patent number: RE37004
    Abstract: 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: Grant
    Filed: August 22, 1997
    Date of Patent: December 26, 2000
    Assignee: Dystar Japan Ltd.
    Inventors: Yousuke Takahashi, Yukihara Shimizu, Toshio Hihara, Kiyoshi Himeno