Patents Assigned to Dystar Japan Ltd.
  • Patent number: 5922089
    Abstract: A process for dyeing a polyester or polyester-containing textile material at pH 8 to pH 11, which is characterized by applying one or more monoazo dyes of the formula I ##STR1## in which X is (C.sub.1 -C.sub.3)-alkyl,R is (C.sub.1 -C.sub.6)-alkyl andR.sup.1 and R.sup.2, independently of one another, are linear (C.sub.2 -C.sub.4) -alkyl, R.sup.1 and R.sup.2, independently of one another, being (C.sub.3 -C.sub.4)-alkyl if R is methyl.
    Type: Grant
    Filed: December 18, 1997
    Date of Patent: July 13, 1999
    Assignee: Dystar Japan Ltd.
    Inventor: Ulrich Buhler
  • Patent number: 5917121
    Abstract: The present invention relates to the .beta. and .gamma. modifications of the dye of the formula (I) ##STR1## as well as to a process for their preparation and their use for dyeing and printing textile materials of polyester and/or cellulose esters or blended fabrics of these materials and wool or cellulose.
    Type: Grant
    Filed: September 5, 1997
    Date of Patent: June 29, 1999
    Assignees: Dystar Textilfarben GmbH & Co. Deutschland KG, Dystar Japan Ltd.
    Inventors: Ulrich Buhler, Hubert Kruse, Heinz G. Zorn, Klaus-Wilfried Wanken
  • Patent number: 5902356
    Abstract: The present invention relates to liquid or pulverulent textile dye preparations including one or more dispersants based on an alkoxylated and carboxylic-esterified castor oil of the general formula I ##STR1## where A, X.sup.1, X.sup.2, Z.sup.1, Z.sup.2, Z.sup.3, n.sup.1 and n.sup.2 are each as defined in Claim 1.
    Type: Grant
    Filed: July 3, 1997
    Date of Patent: May 11, 1999
    Assignee: DyStar Japan Ltd.
    Inventors: Ulrich Buhler, Hubert Kruse, Rainer Az
  • Patent number: 5824117
    Abstract: The present invention relates to the dyestuff of the formula I ##STR1## modifications of this dyestuff which are stable during dyeing, processes for the preparation thereof and their use for dyeing and printing synthetic fiber materials.
    Type: Grant
    Filed: June 28, 1996
    Date of Patent: October 20, 1998
    Assignee: Dystar Japan Ltd.
    Inventors: Ulrich Buhler, Jurgen Kuhlwein, Hubert Kruse
  • Patent number: 5760197
    Abstract: Hydroxyquinolone monoazo dyestuffs of the formula I ##STR1## in which D is an organic radical such as one of the disclosed aromatic radicals, and R is substituted or unsubstituted alkyl, benzyl, phenyl, phenoxy, or alkoxy (most preferably C.sub.1 -C.sub.6 -alkyl) are especially well suited to dyeing and printing of hydrophobic materials and other dyeing or printing applications. The dyestuffs are prepared by diazotizing an amine (D--NH.sub.2) and coupling the diazotization product to a hydroxyquinolone compound.
    Type: Grant
    Filed: July 3, 1996
    Date of Patent: June 2, 1998
    Assignee: Dystar Japan Ltd.
    Inventor: Ulrich Buhler
  • 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: 5639282
    Abstract: The present invention relates to a process for dyeing polyester or polyester-containing textile materials at pH 8 to pH 11, characterized in that one or more monoazo dyestuffs of the general formula I ##STR1## wherein D is a substituted phenyl radical of the general formula II ##STR2## or 5,6-dichlorobenzothiazol-2-yl6,7-dichlorobenzothiazol-2-yl6-chlorobenzothiazol-2-yl5-nitrobenzothiazol-2-yl6-nitrobenzothiazol-2-yl6-methylsulphonylbenzothiazol-2-yl or5-nitrobenzoisothiazol-3-ylandx.sup.1, x.sup.2, x.sup.3, x.sup.4, y.sup.1, y.sup.2, y.sup.3, r.sup.1, r.sup.2 and r.sup.3 are as defined in claim 1, are employed.
    Type: Grant
    Filed: December 14, 1995
    Date of Patent: June 17, 1997
    Assignee: Dystar Japan, Ltd.
    Inventor: Ulrich Buhler
  • 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: 5505742
    Abstract: A method for dyeing hydrophobic fibers black, wherein a mixed black dye is used which comprises a blue color component containing at least 70 wt % of a disperse dye of the following formula (I): ##STR1## wherein X is a chlorine atom or a bromine atom, and R is a methyl group or an ethyl group.
    Type: Grant
    Filed: December 20, 1994
    Date of Patent: April 9, 1996
    Assignee: Dystar Japan Ltd.
    Inventors: Kiyoshi Himeno, Kazuhisa Konishi, Ryouichi Sekioka
  • Patent number: 5496380
    Abstract: A dispersed dye composition which is (A) a combination of blue dye composition (1) and red dye composition (2); (B) a combination of blue dye composition (1) and yellow dye composition (3); or (C) a combination of blue dye composition (1), red dye composition (2) and yellow dye composition (3); wherein blue dye composition (1) consists of from 35 to 55 weight percent of a compound of Formula (I), from 35 to 55 weight percent of a compound of Formula (II) and from 2 to 20 weight percent of a compound of Formula (III); red dye composition (2) consists of at least one red dye selected from the group of compounds of Formulas (IV-1) and (IV-2); and yellow dye composition (3) consists of at least one dye within the scope of the compound of Formula (V).
    Type: Grant
    Filed: May 18, 1995
    Date of Patent: March 5, 1996
    Assignee: Dystar Japan Ltd.
    Inventors: Hideaki Imafuku, Takashi Fujita, Toshikazu Tamiya, Kuniko Kira
  • 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: 5494492
    Abstract: A disperse dye composition comprising compounds of the formulae (I) and (II): ##STR1## wherein each of R.sup.1 and R.sup.5 is a methyl group or an ethyl group, and each of R.sup.2, R.sup.3 and R.sup.4 is a C.sub.1-5 alkyl group, wherein the weight ratio of the compound of the formula (I) to the compound of the formula (II) is within a range of from 95:5 to 5:95.
    Type: Grant
    Filed: October 6, 1994
    Date of Patent: February 27, 1996
    Assignee: Dystar Japan Ltd.
    Inventors: Kiyoshi Himeno, Kazuhisa Konishi, Ryouichi Sekioka
  • 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