Fiber- Or Substrate-reactive Azo Compound Patents (Class 534/617)
  • Patent number: 4731441
    Abstract: Water-soluble monoazo and disazo compounds having fiber-reactive dye properties which are suitable for dyeing carbamoyl- and hydroxyl-containing materials, in particular cellulose fiber materials, and containing as diazo components an optionally substituted phenyl radical or naphthyl radical or a phenylazophenyl, phenylazonaphthyl, naphthylazophenyl or naphthylazonaphthyl radical, one of these radicals containing bonded in the diazo component a vinylsulfonyl, .beta.-thiosulfatoethylsulfonyl, .beta.-phosphatoethylsulfonyl, .beta.-chloroethylsulfonyl or .beta.-sulfatoethylsulfonyl group, and as coupling component that of a naphthol, aminonaphthaline or aminobenzene having a fiber-reactive grouping of the general formula ##STR1## in which the two R.sup.1 s, identical to or different from each other, denote a hydrogen atom or an optionally substituted alkyl group of 1 to 4 carbon atoms, R is a hydrogen atom or a sulfo group and Y represents the vinyl group, a .beta.-thiosulfatoethyl, .beta.-phosphatoethyl, .beta.
    Type: Grant
    Filed: March 19, 1986
    Date of Patent: March 15, 1988
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Marcos Segal, Michael Kunze
  • Patent number: 4730038
    Abstract: Water-soluble disazo compounds having fiber-reactive dyestuff properties of the general formula (1) ##STR1## in which D.sub.1 and D.sub.2 are identical or different and each represents a phenyl radical or a naphthyl radical, both of which are substituted by a group of the formula moiety Y or formula moiety Z defined below and can additionally be substituted by one or two substituents from the group comprising sulfo, chlorine, bromine, lower alkyl and lower alkoxy, Z is a group of the formula (2a), (2b), (2c), (2d), (2e) or (2f) ##STR2## in which R denotes an alkyl group having 1 to 4 C atoms and X denotes a chlorine atom, the acetoxy group, the thiosulfate group, the phosphate group or the sulfato group; Y is a radical of the formula (3) ##STR3## in which R.sup.1 and R.sup.
    Type: Grant
    Filed: December 16, 1985
    Date of Patent: March 8, 1988
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Fritz Meininger, Ernst Hoyer, Rudolf Fass
  • Patent number: 4725674
    Abstract: Water-soluble monoazo and disazo compounds which have fiber-reactive dyestuff properties and containing as diazo component an optionally substituted phenyl radical or naphthyl radical or an optionally substituted phenylazophenyl, phenylazonaphthyl, naphthylazophenyl or naphthylazonaphthyl radical, and as coupling component that of a naphthol, aminonaphthaline or aminobenzene and as fiber-reactive group a group of the formula ##STR1## in which both R.sup.1 s, identical to or different from one another, denote a hydrogen atom or an optionally substituted alkyl group of 1 to 4 carbon atoms, R is a hydrogen atom or a sulfo group and Y represents a vinyl group or a .beta.-thiosulfatoethyl, .beta.-phosphatoethyl, .beta.-chloroethyl or .beta.-sulfatoethyl group, this fiber-reactive grouping being bonded to the radical of the coupling component.
    Type: Grant
    Filed: March 19, 1986
    Date of Patent: February 16, 1988
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Marcos Segal, Michael Kunze
  • Patent number: 4725675
    Abstract: Water-soluble azo compounds of the formula (1) ##STR1## in which R is hydrogen or alkyl of 1 to 4 carbon atoms, X is alkyl of 1 to 6 carbon atoms substituted by carboxy or sulfo, or is phenyl substituted by 1 or 2 sulfo or carboxy or both, and Z is vinyl, .beta.-thiosulfatoethyl or .beta.-sulfatoethyl and M is hydrogen or the equivalent of a metal, and in which the second sulfo group in the naphthalene is bonded in the m-position or p-position relative to the acylated amino group. The new azo compounds are very valuable dyestuffs having fiber-reactive properties, and give color-fast and deep dyeings and prints on fiber materials made of cellulose or synthetic or natural polyamide fibers.
    Type: Grant
    Filed: December 5, 1983
    Date of Patent: February 16, 1988
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Fritz Meininger, Joachim Otten
  • Patent number: 4709018
    Abstract: Reactive dyes of the formula ##STR1## in which D is the radical of an organic dye of the monoazo, polyazo, metal complex azo, anthraquinone, phthalocyanine, formazan, azomethine, dioxazine, phenazine, stilbene, triphenylmethane, xanthene, thioxanthone, nitroaryl, naphthoquinone, pyrenequinone or perylenetetracarbimide series, R is hydrogen or substituted or unsubstituted C.sub.1-4 -alkyl, X is a substituent which is detatchable in the form of an anion, A is arylene or C.sub.2-6 -alkylene, Y is a --CH.dbd.CH.sub.2 or --CH.sub.2 CH.sub.2 --Z radical, Z is an inorganic or organic radical which is detachable under alkaline conditions, B is hydrogen or the radical of a substituted or unsubstituted hydrocarbon, T is a negative substituent, and n is 1 or 2, are suitable for dyeing or printing cellulose-containing and nitrogen-containing materials and produce, in high colouristic yields, dyeings and prints having good fastness properties.
    Type: Grant
    Filed: August 30, 1984
    Date of Patent: November 24, 1987
    Assignee: Ciba-Geigy Corporation
    Inventor: Karl Seitz
  • Patent number: 4707545
    Abstract: Lithium salts of anionic dyes are prepared by first converting another salt of this anionic dye in aqueous solution or suspension by means of a compound which releases calcium ions into the water-insoluble or sparingly water-soluble calcium salt of the dye, which is separated from the aqueous medium and is then converted to an aqueous suspension by treatment with lithium sulfate or lithium hydrogensulfate or a mixture thereof in an equivalent amount of each or in an excess of up to 10% into its lithium salt.
    Type: Grant
    Filed: November 26, 1985
    Date of Patent: November 17, 1987
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Fritz Meininger, Ludwig Schlafer
  • Patent number: 4701524
    Abstract: 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.
    Type: Grant
    Filed: November 5, 1985
    Date of Patent: October 20, 1987
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yutaka Kayane, Hirokazu Sawamoto, Takashi Omura, Naoki Harada, Akira Takeshita
  • Patent number: 4701523
    Abstract: Water-soluble disazo compounds which have fiber-reactive dye properties, which are suitable for dyeing carboxamido- and/or hydroxy- containing materials, in particular cellulose fiber materials, and which contain as bivalent coupling component 1-amino-8-naphthol-3,6- or -4,6-disulfonic acid and as diazo components an optionally substituted phenyl radical or naphthyl radical, one or both of the diazo components possessing a fiber-reactive group of the general formula ##STR1## in which the two R.sup.1, identical to or different from each other, denote a hydrogen atom or an optionally substituted alkyl group of 1 to 4 carbon atoms, R is a hydrogen atom of a sulfo group and Y represents the vinyl group or a .beta.-thiosulfatoethyl, .beta.-phosphatoethyl, .beta.-chloroethyl or .beta.-sulfatoethyl group, and it being possible for one of these diazo components also to contain, as substituent in place of this fiber-reactive grouping, a fiber-reactive group of the formula --SO.sub.
    Type: Grant
    Filed: May 13, 1986
    Date of Patent: October 20, 1987
    Inventors: Marcos Segal, Michael Kunze
  • Patent number: 4698421
    Abstract: A compound, or a salt thereof, represented by the following formula, ##STR1## wherein A is a substituted or unsubstituted phenylene or naphthylene group, B is ##STR2## in which R.sub.3 is a hydrogen atom or a lower alkyl, lower alkoxy, acylamino or ureido group, and R.sub.4 is a hydrogen atom or a lower alkyl or lower alkoxy group, R.sub.1 and R.sub.3 are independently a hydrogen atom or a substituted or unsubstituted lower alkyl group, X is a substituted or unsubstituted amino, lower alkoxy, substituted phenoxy or sulfo 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 m is 2 or 3, which is useful for dyeing hydroxyl group- or amide group-containing fiber materials to give dyed products of a brown color having excellent fastness properties with good build-up property.
    Type: Grant
    Filed: June 7, 1985
    Date of Patent: October 6, 1987
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yutaka Kayane, Hirokazu Sawamoto, Takashi Omura, Naoki Harada
  • Patent number: 4686286
    Abstract: A disazo reaction dyestuff for cellulose fibers which is of the formula: ##STR1## wherein D is a residue of a monoazo dye, R.sup.1 is hydrogen or lower alkyl, and X is a group: ##STR2## wherein R.sup.2 and R.sup.3 are each hydrogen, methyl, methoxy or --SO.sub.3 M, Y is an aromatic or aliphatic divalent residue and M is hydrogen or an alkali metal.
    Type: Grant
    Filed: May 17, 1985
    Date of Patent: August 11, 1987
    Assignee: Mitsubishi Chemical Industries Limited
    Inventors: Toshio Niwa, Yoshiaki Katoh
  • Patent number: 4677199
    Abstract: Compounds of the general formula I ##STR1## wherein R.sup.1 is hydrogen, fluorine, chlorine or bromine, R.sup.2 is hydrogen, fluorine, chlorine, bromine, or nitro, B is aliphatic or a sulfo-substituted phenylene radical, and X is a dye radical, are useful for dyeing hydroxyl-containing textile material, in particular cotton.
    Type: Grant
    Filed: September 19, 1985
    Date of Patent: June 30, 1987
    Assignee: BASF Aktiengesellschaft
    Inventors: Dietmar Augart, Heinz Eilingsfeld, Heinz Krueger, Hartmut Lardon, Ortwin Schaffer, Guenther Seybold
  • Patent number: 4667057
    Abstract: Compounds of the formula ##STR1## in which X is a radical of the formula --CHCl--CH.sub.2 Cl, --CHBr--CH.sub.2 Br, --CCl.dbd.CH.sub.2 or --CBr.dbd.CH.sub.2,are prepared by halogenation of acryloylamidoglycolic acid and optionally elimination of hydrogen halide from the dihalogeno compounds by the action of alkali. The compounds are suitable as intermediates for reactive dyes.
    Type: Grant
    Filed: September 28, 1982
    Date of Patent: May 19, 1987
    Assignee: Ciba-Geigy Corporation
    Inventors: Jean-Marie Adam, Arthur Buhler
  • Patent number: 4667022
    Abstract: A red reactive dye represented by a free acid of the formula, ##STR1## wherein X is a hydrogen atom, a methyl, methoxy or sulfonic acid group, Y is --CH.dbd.CH.sub.2, --CH.sub.2 CH.sub.2 Y.sub.1 or --CH.sub.2 CH.sub.2 OY.sub.2 (in which Y.sub.1 is a halogen atom, and Y.sub.2 is the residue of polybasic acids), R is a C.sub.1 -C.sub.4 alkyl group, R.sub.1 and R.sub.2 are each a hydrogen atom, a methyl or ethyl group, and the azo group is located on a meta-or para-position of the benzene ring A with respect to the --NR.sub.2 -- group and the sulfonic acid group on the benzene ring A is adjacent to the azo group. This dye is suitable for dyeingcellulose fibers red to afford dyeings superior in fastnesses, acid stability, build-up property, level dyeing property and white dischargeability.
    Type: Grant
    Filed: February 13, 1981
    Date of Patent: May 19, 1987
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Toshio Nakamatsu, Yoshikazu Matsuo, Yasuo Tezuka
  • Patent number: 4663440
    Abstract: A brown reactive dye represented by a free acid of the formula, ##STR1## wherein R is a hydrogen atom or a C.sub.1 to C.sub.4 alkyl group, X is --SO.sub.2 CH.sub.2 CH.sub.2 Cl, --SO.sub.2 CH.dbd.CH.sub.2, --SO.sub.2 CH.sub.2 CH.sub.2 OSO.sub.3 H or --SO.sub.2 CH.sub.2 CH.sub.2 OPO.sub.3 H.sub.2, rings A, B and C are each a benzene or naphthalene ring which may have other substituent, m is 0 to 3 and n is 0 to 1.This dye is suitable for dyeing cellulose fibers brown to afford dyeings superior in fastnesses, acid stability, build-up property and level dyeing property.
    Type: Grant
    Filed: May 26, 1981
    Date of Patent: May 5, 1987
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Takashi Omura, Masaki Sunami, Yasuo Tezuka
  • Patent number: 4659806
    Abstract: Copper complexes of disazo dyestuffs of the formula ##STR1## wherein R, Z, K and A have the meaning given in the description, and their use for dyeing and printing materials containing hydroxyl groups or amide groups, such as textile fibres, filaments and fabrics of wool, silk or synthetic polyamide or polyurethane fibres, and for dyeing and printing natural or regenerated cellulose in shades which are fast to washing.
    Type: Grant
    Filed: June 11, 1980
    Date of Patent: April 21, 1987
    Assignee: Bayer Aktiengesellschaft
    Inventor: Horst Jager
  • Patent number: 4649193
    Abstract: Water-soluble fibre-reactive dyestuffs containing one or two fibre-reactive groups of the vinylsulfone series and one or two fibre-reactive groups of the fluoro-s-triazinyl-amino series. These dyestuffs can be applied on fibre materials containing hydroxy and/or carbonamide groups by known application and fixation techniques for fibre-reactive dyes to yield deep and fast dyeings on these materials.
    Type: Grant
    Filed: August 1, 1983
    Date of Patent: March 10, 1987
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Fritz Meininger, Joachim W. Otten, deceased, by Ursula Otten, heir, by Anna G. Rudolph nee Otten, heir
  • Patent number: 4647286
    Abstract: Reactive dyes of the formula ##STR1## in which M is twice-coupled 1-amino-8-hydroxynaphthalene-3,6-disulfonic acid, 1-amino-8-hydroxynaphthalene-4,6-disulfonic acid, 1-amino-8-hydroxynaphthalene-4-sulfonic acid or 2-amino-5-hydroxynaphthalene-7-sulfonic acid, A and B, independently of each other, are each sulfophenylene or sulfonaphthylene which can be further substituted, and X.sub.1 and X.sub.2 are each a 2,4-difluoro-5-chloropyrimid-6-yl radical, subject to the condition that A and B together contain at least 3 sulfo groups, are particularly suitable for dyeing and printing cellulose-containing fibre materials and produce, in high dyeing yield, dyeings and prints having good fastness properties.
    Type: Grant
    Filed: August 20, 1985
    Date of Patent: March 3, 1987
    Assignee: Ciba-Geigy Corporation
    Inventor: Karl Seitz
  • Patent number: 4645832
    Abstract: Reactive azo dyes represented by the general formula (I) or (II): ##STR1## wherein M is a hydrogen atom or an alkali metal, R.sup.1 is a hydrogen atom, a chlorine atom, a lower alkyl group, a lower alkoxy group, a nitro group or a carboxyl group, R.sup.2 and R.sup.8 are a lower alkyl group, a lower alkoxy group or a sulfonic acid group, R.sup.3, R.sup.7 and R.sup.9 are a hydrogen atom, a lower alkyl group, a lower alkoxy group, an acetylamino group or a sulfonic acid group, R.sup.4 and R.sup.5 are a hydrogen atom, a methyl group, a methoxy group or a sulfonic acid group, R.sup.6 is a hydrogen atom, a lower alkyl group, a lower alkoxy group or a sulfonic acid group, Z.sup.1 is a chlorine atom, a fluorine atom, an aliphatic or an aromatic amino residual group, a methoxy group or a phenoxy group, Z.sup.2 is the same one as Z.sup.1 when Z.sup.3 is ##STR2## Z.sup.2 is a chlorine atom or a fluorine atom when Z.sup.
    Type: Grant
    Filed: April 9, 1985
    Date of Patent: February 24, 1987
    Assignee: Mitsubishi Chemical Industries Limited
    Inventors: Toshio Niwa, Yoshiaki Kato
  • Patent number: 4644058
    Abstract: A monoazo compound represented by a free acid of the formula: ##STR1## wherein R.sub.1 and R.sub.2 independently represent a hydrogen atom, or an alkyl, aralkyl or cyclohexyl group; R.sub.3 represents a hydrogen atom or a methyl or sulfonic acid group; R.sub.4 represents a hydrogen atom or an alkyl group; A represents an oxygen atom or --NH--; X.sub.1 and X.sub.2 independently represent a hydrogen or chlorine atom, or a methyl, methoxy, carboxyl or sulfonic acid group; and Y represents --CH.dbd.CH.sub.2 or --CH.sub.2 CH.sub.2 Z in which Z represents a halogen atom, --OSO.sub.3 H or --OPO.sub.3 H.sub.2. This compound is used for dyeing cellulose fibers to give dyed products of yellow to reddish yellow having excellent fastnesses, particularly chlorine fastness.
    Type: Grant
    Filed: November 18, 1982
    Date of Patent: February 17, 1987
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yasutaka Shimidzu, Naoki Harada, Yasuo Tezuka
  • Patent number: 4626589
    Abstract: 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.
    Type: Grant
    Filed: February 7, 1985
    Date of Patent: December 2, 1986
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Takashi Omura, Yutaka Kayane, Mikoto Takahashi, Tetsuya Miyamoto, Akira Takeshita, Naoki Harada, Katsumasa Otake
  • Patent number: 4622390
    Abstract: Water-soluble disazo dyestuffs of the formula ##STR1## which contain a 1-amino-8-naphthol-3,6- or -4,6-disulfonic acid moiety as a bivalent coupling component and which contain diazo components with fibre-reactive groups characterized by the inclusion of one or two chloro-triazinyl groups and one or two of the six groups defined by the substituent Z, namely, ##STR2## each of which are connected to the benzene moiety of the diazo component; the chloro-triazinyl group is further substituted by a substituted or unsubstituted phenylamino or substituted or unsubstituted naphthylamino group, a substitutent of which may be one of the six groups defined by the Z substituent; if there is only one chloro-triazinyl group in the compound, then the diazo component is also substituted by one of the Z substituents; these compounds are dyestuffs which exhibit a good fixation degree of the dyestuffs in fabrics.
    Type: Grant
    Filed: September 9, 1985
    Date of Patent: November 11, 1986
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Fritz Meininger, Ernst Hoyer, Joachim W. Otten, deceased, by Ursula Otten, heir, by Anna G. Rudolph nee Otten, heir, Rudolf Fass
  • Patent number: 4618671
    Abstract: 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.
    Type: Grant
    Filed: December 17, 1984
    Date of Patent: October 21, 1986
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yutaka Kayane, Tetsuya Miyamoto, Takashi Omura, Hirokazu Sawamoto, Naoki Harada, Akira Takeshita
  • Patent number: 4558040
    Abstract: Certain miticidal (2-alkyl-3,4-dihydro-2H-1-benzopyran-8-yl)diazenecarboxylic acid esters.
    Type: Grant
    Filed: December 3, 1984
    Date of Patent: December 10, 1985
    Assignee: Shell Oil Company
    Inventors: Kurt H. Pilgram, Richard D. Skiles
  • Patent number: 4544738
    Abstract: A dye of the formula ##STR1## wherein R.sup.1 is is fluorine, chlorine, bromine, methyl, ethyl, cyano, carboxyl, nitro, tribfluoromethyl, methylsulfonyl, phenylsulfonyl, acetyl, C.sub.1 -C.sub.4 alkoxy, phenoxy, chlorophenoxy or benzoyl; R.sup.2 is hydrogen, chlorine, bromine, methyl, ethyl, C.sub.1 -C.sub.4 alkoxy, benzthiazol-2-yl, 6-methylbenzthiazol-2-yl, acetylamino, carboxyl aminosulfonyl, or aminocarbonyl; R.sup.3 is hydrogen chlorine, bromine or methyl; R.sup.5 is hydrogen, methyl, methoxy or ethoxy; and X is fluorohydroxyphosphonyl or dihydroxyphosphonyl. The dye of the present invention is useful in the dyeing of cellulose-containing material, polyamides and leather. The high tinctorial strength of the dyes and the very good lightfastness and wetfastness properties of the dyeings are particularly noteworthy.
    Type: Grant
    Filed: September 24, 1980
    Date of Patent: October 1, 1985
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans Baumann, Hermann Kaack
  • Patent number: 4530996
    Abstract: A compound represented by a free acid of the formula: ##STR1## wherein D is ##STR2## (R.sub.1 and R.sub.2 independently represent hydrogen, methyl or methoxy) or ##STR3## (n is 0 or 1, the mark * signifies the position of linkage to --N.dbd.N-- and the mark # signifies the position of linkage to Q mentioned below); Q is --SO.sub.2 CH.dbd.CH.sub.2 or --SO.sub.2 CH.sub.2 CH.sub.2 R (R is a group capable of being split off by the action of alkali); one of X.sub.1 and X.sub.2 is hydrogen and the other is a sulfonic acid group; and m is 0 or 1, which is useful for dyeing cellulose fibers a blue-black color with good dyeability and excellent fastnesses, particularly chlorine fastness.
    Type: Grant
    Filed: June 4, 1982
    Date of Patent: July 23, 1985
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Takashi Omura, Naoki Harada, Yasuo Tezuka