Azo Patents (Class 534/573)
  • Patent number: 4952681
    Abstract: Compounds of the formula I ##STR1## where X is fluorine, chlorine, bromine, SO.sub.2 E or unsubstituted or substituted hydroxyl or mercapto, E is alkyl, alkenyl, cycloalkyl, aralkyl, aryl, chlorine or unsubstituted or substituted hydroxyl or amino, Y is cyano, nitro, alkanoyl, aroyl, alkylsulfonyl, arylsulfonyl, carboxyl, a carboxylic ester group or unsubstituted or substituted carbamyl, T is hydrogen, C.sub.1 -C.sub.4 -alkyl, a radical which can be introduced by electrophilic substitution or a radical of the formula --CH.dbd.B, in which B is a radical of a methylene-active compound or of an amine, and K is a radical of a coupling component, are disclosed. They are useful for dyeing synthetic fibers or plastics.
    Type: Grant
    Filed: July 27, 1988
    Date of Patent: August 28, 1990
    Assignee: Sandoz AG
    Inventors: Guenter Hansen, Ernst Schefczik, Karl-Heinz Etzbach, Helmut Reichelt, Hermann Loeffler
  • Patent number: 4952677
    Abstract: Reddish-brown to yellow shade colorants suitable for ribbon and ball point inks are produced from the glassy waste by-product of pararosaniline manufacture by slurrying the residue in mineral acid, diazotizing, and coupling. the resulting colorants are useful in preparing inks.
    Type: Grant
    Filed: September 15, 1988
    Date of Patent: August 28, 1990
    Assignee: BASF Corporation
    Inventors: Floyd G. Spence, Louis R. de Alvare, Robert J. Allen
  • Patent number: 4941997
    Abstract: The invention relates to compounds of formula I ##STR1## wherein R.sup.1 is C.sub.12 -C.sub.30 alkyl, R.sup.2 is hydrogen or C.sub.1 -C.sub.30 alkyl, R.sup.3 is C.sub.1 14 Calkyl or C.sub.1 -C.sub.3 alkoxy, R.sup.4 may have one of the meanings of R.sup.3 or is halogen, k and n are each independently of the other 0, 1 or 2, and R.sup.5 and R.sup.6 are each independently of the other C.sub.1 -C.sub.4 alkyl, any of which alkyl groups as defined herein may also be partly fluorinated or perfluorinated, with the proviso that R.sup.1 is alkyl of not less than 18 carbon atoms if R.sup.2 is hydrogen or alkyl of less than 12 carbon atoms.From these compounds it is possible to prepare molecular aggregates, especially LB layer systems, which have reversible thermochromic and solvatochromic properties. The invention also relates to intermediates of formula II ##STR2## wherein R.sup.1, R.sup.2, R.sup.3 and n are as defined above.
    Type: Grant
    Filed: July 6, 1988
    Date of Patent: July 17, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Gero Decher, Bernd Tieke
  • Patent number: 4940492
    Abstract: Colorant mixtures for use in printing inks contain isoquinoline-azo pigments of the formula I ##STR1## where X is chlorine, bromine, C.sub.1 -C.sub.4 -alkoxy or nitro,n is 1, 2 or 3, and the ring A can be substituted, and an isoquinoline-azo dye of the formula II ##STR2## where Y is C.sub.6 -C.sub.20 -alkoxy which may be interrupted by one or more oxygen atoms, and the ring B can be substituted.
    Type: Grant
    Filed: June 22, 1988
    Date of Patent: July 10, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Heinrich Kowarsch, Johannes P. Dix
  • Patent number: 4937325
    Abstract: A monoazo dyestuff composition comprising at least two different individual compounds of the formula ##STR1## wherein R.sup.1 and R.sup.2, independently of each other, are linear or branched alkyl having 1 to 4 carbon atoms and R is linear or branched alkyl having 1 to 5 carbon atoms, and where said individual compounds differ from each other in at least the R moiety. The monoazo dyestuff mixtures are used for the dyeing and printing of hydrophobic fibers such as high molecular weight polyesters of their mixtures with natural fiber material.
    Type: Grant
    Filed: December 12, 1988
    Date of Patent: June 26, 1990
    Assignees: Cassella Aktiengesellschaft, Tokico Ltd.
    Inventors: Ulrich Buhler, Klaus Hofmann, Hiroshi Mitsuhashi, Harutsugu Ushiota, Akiharu Odagiri, Gen Kano, Susumu Sakamoto
  • Patent number: 4935502
    Abstract: When a diamine of the formula ##STR1## in which n is 1 to 4, is bis-diazotized and the resulting bis-diazo compound is coupled with 2 moles of one or more coupling components of the formula ##STR2## in which R.sup.1 is hydrogen, chlorine, bromine, methyl or methoxy and R.sup.2 is hydrogen or, if R.sup.1 is hydrogen, also methyl or ethyl, disazo compounds are obtained which are colorants. Due to their high fastness to light and to migration and their heat stability and dispersibility, these compounds are useful for pigmenting high molecular weight materials, especially polyolefins.
    Type: Grant
    Filed: August 22, 1989
    Date of Patent: June 19, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Rudolf Kuhne, Heinrich Hamal
  • Patent number: 4931550
    Abstract: The dye of the formula: ##STR1## which is suitable for use in aqueous inks, especially for ink jet printing.
    Type: Grant
    Filed: May 5, 1987
    Date of Patent: June 5, 1990
    Assignee: Imperial Chemical Industries PLC
    Inventors: Arthur Quayle, Cecil V. Stead
  • Patent number: 4929720
    Abstract: Isothiazole dyes of the formula ##STR1## where X is substituted or unsubstituted C.sub.1 -C.sub.8 -alkyl or substituted or unsubstituted phenyl,Y is hydrogen, cyano, chlorine or bromine,R.sup.1 is hydrogen, C.sub.1 -C.sub.4 -alkyl or phenyl,R.sup.2 is hydrogen, cyano, carbamoyl, C.sub.1 -C.sub.4 -monoalkyl- or -dialkyl-carbamoyl, C.sub.1 -C.sub.6 -alkanoyl, C.sub.1 -C.sub.6 -alkoxycarbonyl or 2-(C.sub.1 -C.sub.4 -alkoxy)-ethoxycarbonyl andR.sup.3 is hydrogen, C.sub.1 -C.sub.8 -alkyl which may be substituted and/or interrupted by one or two oxygen atoms, or is C.sub.5 -C.sub.7 -cycloalkyl, C.sub.3 -C.sub.6 -alkenyl or phenyl, are useful for dyeing synthetic fibers.
    Type: Grant
    Filed: November 10, 1988
    Date of Patent: May 29, 1990
    Assignee: Basf Aktiengesellschaft
    Inventors: Guenter Hansen, Ernst Schefczik, Helmut Reichelt
  • Patent number: 4923973
    Abstract: 1:2 Cobalt complex dyes of the general formula I ##STR1## in which X.sub.1 is nitro or hydrogen, X.sub.2 is nitro, hydrogen, chlorine or methyl, Y.sub.1 is nitro or hydrogen, Y.sub.2 is nitro, hydrogen, chlorine or methyl, m and n, independently of each other, are each 1, 2 or 3, and Ka.sup.+ is a cation, and one of each pair of substituents X.sub.1 or X.sub.2 and Y.sub.1 or Y.sub.2 is nitro and the other is as defined but not nitro are especially suitable for dyeing wool or polyamide and, in particular, leather.
    Type: Grant
    Filed: July 17, 1989
    Date of Patent: May 8, 1990
    Assignee: Ciba-Geigy Corporation
    Inventor: Alois Puntener
  • Patent number: 4923972
    Abstract: Liquid formulations of basic azo dyes are prepared from unsubstituted or C.sub.1 -C.sub.4 -alkyl- or C.sub.1 -C.sub.4 -alkoxy-substituted m-phenylenediamine by diazotizing and coupling in carboxylic acid solution, which comprises performing the reaction with 0.76 to 0.95 mole of nitrile, calculated as nitrous acid and based on 1 mole of m-phenylenediamine, and then heating the resulting reaction mixture at from 60.degree. C. to the boiling point of the reaction mixture.
    Type: Grant
    Filed: April 14, 1988
    Date of Patent: May 8, 1990
    Assignee: BASF Aktiengesellschaft
    Inventor: Karl Schmeidl
  • Patent number: 4910299
    Abstract: Disperse dyes suitable for dyeing textile material composed of polyester dyes of the formula ##STR1## in which D is the radical of a substituted or unsubstituted, homocyclic or heterocyclic diazo component belonging to the series comprising thienyl, thiazolyl, isothiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, benzothiazolyl, benzoisothiazolyl, pyrazolyl, imidazolyl or phenyl,X is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, acylamino, halogen or a group of the formula -NH-CO-NHQ in which Q is hydrogen, C.sub.1 -C.sub.4 -alkyl or phenyl,Y is hydrogen, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.4 -alkoxy,R is hydrogen, C.sub.1 -C.sub.12 -alkyl, C.sub.2 -C.sub.12 -alkenyl or phenyl, or Y and R, together with the nitrogen atom and the two C atoms linking them, form a 5-membered ring or 6-membered ring,B is a l inear or branched C.sub.2 -C.sub.6 -alkylene radical,W is halogen, C.sub.
    Type: Grant
    Filed: December 2, 1987
    Date of Patent: March 20, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Angelo D. Casa, Peter Liechti, Max Dempfle
  • Patent number: 4904765
    Abstract: Dye mixtures contain an oil-soluble dye and a dye of the formula ##STR1## where D is phenyl which is unsubstituted or substituted by methyl or methoxy, R is hydrogen or methyl, R.sup.1 is hydrogen or C.sub.1 -C.sub.4 -alkyl and R.sup.2 is C.sub.3 - or C.sub.4 -alkyl.The mixtures according to the invention are preferably used for coloring and marking mineral oil products.
    Type: Grant
    Filed: July 14, 1987
    Date of Patent: February 27, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernd Derber, Rudolf Denninger
  • Patent number: 4900812
    Abstract: Compounds of the formula ##STR1## and water-soluble salts thereof each cation of which is independently a non-chromophoric cation, whereinMe is cobalt, copper or nickel,Pc is the phthalocyanine radical,each R.sub.1 and R.sub.2 is independently hydrogen or C.sub.1-6 alkyl,each R.sub.4 is independently hydrogen, halo, hydroxy, C.sub.1-4 alkoxy, C.sub.1-4 alkyl, carboxy or sulfo,each R.sub.6 is hydrogen, cyano, carbamoyl or ##STR2## wherein An .crclbar. is a non-chromophoric anion,each R.sub.7 is hydrogen, C.sub.1-4 alkyl, C.sub.5-6 cycloalkyl, phenyl, benzyl, phenylethyl or carboxy,each W is linear or branched C.sub.2-6 alkylene; linear or branched C.sub.3-6 alkylene monosubstituted by hydroxy; linear or branched C.sub.2-6 alkylene interrupted by ##STR3## wherein R.sub.11 is linear or branched C.sub.
    Type: Grant
    Filed: January 29, 1988
    Date of Patent: February 13, 1990
    Assignee: Sandoz Ltd.
    Inventors: Helmut A. Moser, Roland Wald
  • Patent number: 4894094
    Abstract: Disazo compounds based on 4,4'-diaminodiphenyl compounds contain not less than 50% by weight of a disazo compound of the general formulaA--N.dbd.N--Z--N.dbd.N--B (I)where Z is a radical of an unsubstituted of symmetrically substituted diphenylene, A is a radical of a coupling component of a 1-phenylpyrazolone or of an acetoacetarylide, where the phenyl and the aryl radical is substituted by sulfo or carboxyl groups, and B is a radical of a coupling component based on 1-phenylpyrazolone or acetoacetarylide, which are free of sulfo and/or carboxyl groups.The disazo compounds can be obtained by coupling the tetrazotized diamine H.sub.2 N--Z--NH.sub.2 to the coupling component AH containing an acidic group in a medium containing a mineral acid, and then coupling the product to BH in a buffered medium (pH about 4).The novel disazo compounds are suitable as additives to pigments, in particular azo and disazo pigments, for improving the transparency and heat stability of the pigment particles, and the flow behavior.
    Type: Grant
    Filed: August 19, 1987
    Date of Patent: January 16, 1990
    Assignee: Basf Lacke & Farben Aktiengesellschaft
    Inventors: Wolfgang Ruff, Egon Liedek, Gerhard Berger, Hans W. Sonneborn
  • Patent number: 4894447
    Abstract: Azo dyes of the formula ##STR1## or tautomeric forms thereof, in which: Z is N or CH,X is O, NR.sub.1 or N,W is N or C,K is a coupling component,R is hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.4 -alkoxy, halogen, nitro, --CN, --NHR.sub.1, --NH-acyl, phenoxy, --COOH, COOR.sub.1, --CONHR.sub.1 or substituted or unsubstituted phenyl, R.sub.1 being hydrogen, substituted or unsubstituted C.sub.1 -C.sub.6 -alkyl or substituted or unsubstituted phenyl,M is H.sup..sym., Li.sup..sym., Na.sup..sym., K.sup..sym., NH.sub.4.sup..sym. or the protonated form of a C.sub.4 -C.sub.12 -trialkylamine, of a C.sub.4 -C.sub.12 -diamine or of a C.sub.2 -C.sub.12 -alkanolamine,A is a carbocyclic or nitrogen-containing aromatic radical which can be further substituted, andB is a 1,4-phenylene radical which can be further substituted.
    Type: Grant
    Filed: April 9, 1987
    Date of Patent: January 16, 1990
    Assignee: Ciba-Geigy Corporation
    Inventor: Jean-Marie Adam
  • Patent number: 4889535
    Abstract: Compounds of the formula ##STR1## and mixtures thereof, wherien p1 R.sub.1 is hydrogen, chloro or bromo, p1 R.sub.2 is hydrogen, chloro, bromo or nitro, p1 R.sub.3 is hydrogen, chloro, bromo, nitro or --SCN, p1 R.sub.4 is hydrogen, chloro or bromo, p1 R.sub.5 is hydrogen or C.sub.1-4 alkyl, and p1 R.sub.5 is C.sub.8-14 alkyl,with the provisos that (i) at least one of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is other than hydrogen, (ii) when R.sub.3 is nitro or --SCN, R.sub.2 is other than nitro, and (iii) when two or more of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are halo, then R.sub.3 is one of those halos, are useful as disperse dyes for dyeing substrates such as synthetic and semi-synthetic, hydrophobic, high molecular weight organic materials.
    Type: Grant
    Filed: March 13, 1987
    Date of Patent: December 26, 1989
    Assignee: Sandoz Ltd.
    Inventor: Beat Henzi
  • Patent number: 4888432
    Abstract: 2-Aminothiophenes of the formula ##STR1## wherein R=substituent and n=0-4, are prepared by dehydrogenating ring closure of thioamides of the formula ##STR2## The 2-aminothiophenes are useful for preparing useful azo dyestuffs. A process for preparing a compound of the formula ##STR3## comprising reacting a compound of the formula ##STR4## in which R and n have the abovementioned meanings with a compound of the formula ##STR5## in which T denotes NH.sub.2, aryl or alkyl, in the presence of an acid. An azo dyestuff of the formula ##STR6## in which V denotes Cl, Br or CF.sub.3,W denotes Cl, Br or NO.sub.2,R.sub.1 denotes hydrogen, halogen, alkyl, alkoxy, alkoxyalkyl or aryloxy,R.sub.2 denotes alkenyl or OH-, halogen-, CN-, CO.sub.2 -alkyl-, aryl-, cycloalkyl-, alkoxy-, aryloxy-, OCO-alkyl-, OCO-aryl-, OCONH-alkyl- or OCO.sub.2 -alkyl-substituted alkyl,R.sub.3 denotes hydrogen or identical or different R.sub.2 andR.sub.2 denotes hydrogen, alkyl, alkenyl, cycloalkyl, aralkyl, alkoxy, halogen, CF.sub.
    Type: Grant
    Filed: October 15, 1987
    Date of Patent: December 19, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventor: Rainer Hamprecht
  • Patent number: 4881943
    Abstract: A disperse monoazo dye of the formula: ##STR1## wherein each of R and R.sup.3 represents a lower alkyl radical, R.sup.1 represents a lower alkyl or C.sub.3 -C.sub.6 alkenyl radical andR.sup.2 represents a C.sub.2 -C.sub.6 alkyl radical carrying a hydroxy or acyloxy substituent.
    Type: Grant
    Filed: June 28, 1988
    Date of Patent: November 21, 1989
    Assignee: Imperial Chemical Industries PLC
    Inventors: David Brierley, Ronald W. Kenyon, Denis R. A. Ridyard
  • Patent number: 4873319
    Abstract: Disazo dyes which are suitable for dyeing and printing, especially of paper of all kinds. The dyes correspond to the formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are each an alkyl radical, A is an alkylene radical, n is 1 or 2, V, X, Y and Z are nonionic substituents customarily in azo dyes, K is a pyrimidine coupling and An is an anion.
    Type: Grant
    Filed: September 25, 1987
    Date of Patent: October 10, 1989
    Assignee: Ciba-Geigy Corporation
    Inventor: Willy Stingelin
  • Patent number: 4870164
    Abstract: Symmetrical and asymmetrical disazo compounds of the formula: ##STR1## wherein: the R.sup.1 's are identical or different and are hydrogen, chlorine, bromine, methyl or methoxy;the R.sup.2 's are hydrogen, or, if the R.sup.1 's are hydrogen, the R.sup.2 's are hydrogen, methyl or ethyl, the two R.sup.2 radicals being identical or different; andn is 1 to 4and mixtures of such compounds as colorants, especially for pigmenting high molecular weight organic material.
    Type: Grant
    Filed: January 28, 1985
    Date of Patent: September 26, 1989
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Rudolf Kuhne, Heinrich Hamal
  • Patent number: 4861869
    Abstract: This invention relates to bifunctional coupling agents useful in forming conjugates with biologically useful molecules, such as antibodies. These conjugates can be complexed with radionuclide metal ions to provide materials useful for in vivo diagnostic and therapeutic applications.
    Type: Grant
    Filed: May 29, 1986
    Date of Patent: August 29, 1989
    Assignee: Mallinckrodt, Inc.
    Inventors: Robert A. Nicolotti, Richard T. Dean
  • Patent number: 4855412
    Abstract: Compounds of the general formula ##STR1## where D is a radical of the formula ##STR2## and one of the two radicals L.sup.1 and L.sup.2 is unsubstituted amino and the other the radical ##STR3## where R.sup.1 is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy-C.sub.2 -C.sub.4 -alkyl or C.sub.1 -C.sub.8 -acyloxy-C.sub.2 -C.sub.4 -alkyl,R.sup.2 is C.sub.2 -C.sub.10 -alkylene or C.sub.2 -C.sub.10 -alkylene is interrupted by oxygen,T is C.sub.1 -C.sub.8 -alkanoyl which is unsubstituted or is substituted by chlorine or methoxy,B.sup.1 is C.sub.1 -C.sub.4 -alkyl or benzyl or phenyl, which are each unsubstituted or are each substituted by methyl, methoxy or chlorine,B.sup.2 is B.sup.1, hydrogen, halogen, cyano or C.sub.1 -C.sub.5 -alkoxycarbonyl,X.sup.1 is hydrogen, nitro, cyano, C.sub.1 -C.sub.9 -alkoxycarbonyl, C.sub.1 -C.sub.9 -mono- or -dialkylaminocarbonyl, trifluoromethyl, methylsulfonyl or ethylsulfonyl,X.sup.2 is nitro or C.sub.1 -C.sub.5 -alkoxycarbonyl,X.sup.3 is X.sup.
    Type: Grant
    Filed: April 24, 1987
    Date of Patent: August 8, 1989
    Assignee: BASF Aktiengesellschaft
    Inventors: Johannes Dehnert, Gunther Lamm, Hermann Loeffler
  • Patent number: 4855413
    Abstract: The novel dyes of the general formula I ##STR1## where X is hydrogen or C.sub.1 14 C.sub.4 -alkyl or is phenyl which is unsubstituted or substituted by fluorine, chlorine, bromine, methyl, methoxy or nitro, Y is cyano, a carboxylic ester group or nitro, Z is cyano, acetyl, benzoyl or unsubstituted or substituted carbamyl, or X and Z or Y and Z may simultaneously be a carboxylic ester group, and R.sup.1 and R.sup.2 independently of one another are each hydrogen or unsubstituted or substituted alkyl or aryl, are very useful for dyeing polyesters, polyester/cellulose blends or thermoplastics.
    Type: Grant
    Filed: April 28, 1988
    Date of Patent: August 8, 1989
    Assignee: BASF Aktiengesellschaft
    Inventors: Johannes Dehnert, Gunther Lamm, Hermann Loeffler
  • Patent number: 4843149
    Abstract: A monoazo compound, or a salt thereof, represented by the formula, ##STR1## wherein D is a sulfophenyl group substituted with a methyl, ethyl, methoxy, ethoxy, phenoxy, acetylamino, pripionylamino, benzoylamino, carboxybenzoylamino, maleinylamino or succinylamino group, a naphthyl group substituted with two or three sulfo groups of a group of the formula ##STR2## any one of X.sub.1 or X.sub.2 is a sulfo group and the other is a methoxy or ethoxy group, Y is a fluorine or chlorine atom or an arylamino group substituted with one or two sulfo groups, R is a hydrogen atom or an unsubstituted or substituted lower alkyl group, A is an unsubstituted or substitued phenylene or naphthylene group, and Z is --SO.sub.2 CH.dbd.CH.sub.2 or --SO.sub.2 CH.sub..sub.2 CH.sub.2 Z.sub.1 in which Z.sub.1 is a group capable of being split by the action of an alkali, which is useful as a fiber-reactive dye for dyeing materials in a greenish yellow color excellent in various fastness properties.
    Type: Grant
    Filed: November 13, 1985
    Date of Patent: June 27, 1989
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yutaka Kayane, Hirokazu Sawamoto, Takashi Omura, Naoki Harada, Akira Takeshita
  • Patent number: 4835261
    Abstract: Azo compounds of the formula I ##STR1## where D=diazo componentR.sub.1 and R.sub.2 =alkyl or aralkylX=H, hydrocarbon radical or acylare useful dyestuffs or dyestuff intermediates.
    Type: Grant
    Filed: March 12, 1987
    Date of Patent: May 30, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventor: Klaus Leverenz
  • Patent number: 4831096
    Abstract: Mixtures of azolakanes of varying thermal stabilities at least one of which is an unsymmetrical azoalkane (R--N.dbd.N--R'), are prepared by reacting 4 equivalents of a mixture of two or more primary alkyl, cycloalkyl or aralkylamines with 1 equivalent of sulfuryl chloride in an inert solvent and oxidizing the resulting mixture of sulfamide products with basic bleach. The unsymmetrical azoalkanes can be separated from the symmetrical azoalkanes by a variety of conventional techniques. The azoalkane mixtures are excellent polymerization initiators for vinyl monomers and curing agents for unsaturated polyester resins.
    Type: Grant
    Filed: January 21, 1988
    Date of Patent: May 16, 1989
    Assignee: Pennwalt Corporation
    Inventor: Ronald E. MacLeay
  • Patent number: 4826959
    Abstract: A mixture of an isomer of 2,2'-azobis(2,4-dimethylvaleronitrile) having a low melting point in an amount of about 70% by weight or more and an isomer of 2,2'-azobis(2,4-dimethylvaleronitrile) having a high melting point in an amount of about 30% by weight or less shows excellent solvent solubility, which is higher than that of the isomer having a low melting point. The mixture is useful as a polymerization initiator, and also as a blowing agent.
    Type: Grant
    Filed: January 29, 1988
    Date of Patent: May 2, 1989
    Assignee: Wako Pure Chemical Industries, Ltd.
    Inventors: Motoaki Tanaka, Tsutomu Miyagawa, Hideo Takeuchi
  • Patent number: 4810783
    Abstract: An azo dyestuff of the formula ##STR1## wherein D=a diazo component,R.sub.1 and R.sub.2 =alkyl or aralkyl,R.sub.3 =H, R or OR.sub.1 andR.sub.4 =a hydrocarbon radical or acyl,which are prepared in a simple manner by aminolysis with ammonia or an amine of the formula ##STR2## of an azo compound of the formula ##STR3## these dyestuffs dye polyester fibres in blue-green to green shades with good fastness to light.
    Type: Grant
    Filed: March 3, 1987
    Date of Patent: March 7, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventor: Klaus Leverenz
  • Patent number: 4804747
    Abstract: (i) A compound of the formula: ##STR1## wherein R is H, a metal or a group containing a tetravalent N atom;X is S, O, ##STR2## R.sup.1 is NO.sub.2, CN or COOY; Y is H, C.sub.1-4 -alkyl, a metal or a group containing a tetravalent N atom;R.sup.2 and R.sup.3 are each independently H or a non-hydrophilic aliphatic or cycloaliphatic group containing up to 30 carbon atoms;R.sup.4 and R.sup.5 are each independently H or a non-hydrophilic aliphatic or cycloaliphatic group containing up to 30 carbon atoms; andR.sup.6 and R.sup.7 are each independently H or a non-hydrophilic group containing up to 4 carbon atoms; orR.sup.4 and R.sup.6 together comprise ring fused to Ring A and R.sup.5 and R.sup.7 are as hereinbefore defined; orR.sup.5 and R.sup.7 together comprise ring fused to Ring A and R.sup.4 and R.sup.6 are as hereinbefore defined; orR.sup.2 and R.sup.4 together with the N atom to which R.sup.2 is attached form a ring fused to Ring A and R.sup.3 and R.sup.5 are as hereinbefore defined; orR.sup.3 and R.sup.
    Type: Grant
    Filed: October 16, 1986
    Date of Patent: February 14, 1989
    Assignee: Imperial Chemical Industries PLC
    Inventors: Simon Allen, Paul F. Gordon, Richard A. Hann
  • Patent number: 4799960
    Abstract: A water-soluble dye, free from cellulose reactive groups, of the formula: ##STR1## wherein R.sup.1 is --(C.sub.a H.sub.2a O).sub.m (C.sub.b H.sub.2b O) .sub.n H,R.sup.2 is H or --(C.sub.a H.sub.2a O).sub.m (C.sub.b H.sub.2b O).sub.n H, orR.sup.1 and R.sup.2 together with the nitrogen atom form a morpholine ringa and b are different and from 1 to 8m is from 1 to 10;n is from 0 to 9;q is 1/2 or 1p is 1 or 2L is a transition metal capable of complexing with a dyeM is H, ammonium, or a monovalent metal;Q is H or SO.sub.3 MT is H or C.sub.1-4 -alkyl;D is a substituted azo group;B, E and F are H or substituents;X is NR.sup.1 R.sup.2, NR.sup.3 R.sup.4, --NR.sup.3 --Z--NR.sup.4 --, OR.sup.3, or the residue of a mono- or bis-azo chromophore comprising benzene, naphthalene or mono- or bi- cyclic heteroaryl diazo and coupling components, linked to the triazine nucleus through a primary or secondary amine linking group, wherein R.sup.3 & R.sup.
    Type: Grant
    Filed: November 10, 1986
    Date of Patent: January 24, 1989
    Assignee: Canon Kabushiki Kaisha
    Inventors: Anthony G. W. Baxter, Stephen B. Bostock, David Greenwood
  • Patent number: 4800043
    Abstract: Reddish-brown to yellow shade colorants suitable for ribbon and ball point inks are produced from the glassy waste by-product of pararosaniline manufacture.
    Type: Grant
    Filed: February 24, 1987
    Date of Patent: January 24, 1989
    Assignee: BASF Corporation
    Inventors: Robert J. Allen, Louis Rolando de Alvare, Floyd G. Spence
  • Patent number: 4791194
    Abstract: An azo compound with the following general formula (I): ##STR1## wherein X is selected from the group consisting of hydrogen atom, lower alkyl group, lower alkoxy group, halogen atom and cyano group;Y is phenylene or naphthylene group;Z.sub.1 and Z.sub.2 are independently the divalent group represented by the following formula: ##STR2## wherein A is a divalent group derived from the aromatic hydrocarbon or heterocyclic compound including one or more nitrogen atoms in the ring; andn is 1 or 2,is disclosed. Such compounds are useful in forming a photosensitive layer of an electrophotographic photoreceptor.
    Type: Grant
    Filed: July 25, 1986
    Date of Patent: December 13, 1988
    Assignee: Mitsubishi Chemical Industries, Ltd.
    Inventors: Tetsumi Suzuki, Tetsuo Murayama, Hitoshi Ono, Shinji Aramaki, Michiyo Yokoyama
  • Patent number: 4785083
    Abstract: Mixtures comprising at least two dyes of formula I ##STR1## where R is unsubstituted linear C.sub.3-7 alkyl, with the proviso that at least two different dyes of formula I are each present to the extent of at least 10 mole %, based on the total molar quantity of dyes present, which are useful for dyeing and printing synthetic and semi-synthetic high molecular weight, hydrophobic organic substrates, particularly for rapid dyeing.
    Type: Grant
    Filed: December 27, 1982
    Date of Patent: November 15, 1988
    Assignee: Sandoz Ltd.
    Inventor: Ulrich Zirngibl
  • Patent number: 4776886
    Abstract: A halftone gravure printing ink(A) about 2 to about 20% by weight of colorant,(B) about 10 to about 40% by weight of resin and(C) about 80 to about 50% by weight of solventwherein said colorant comprises azo dyestuff of the formula ##STR1## in which A.sub.1, A.sub.2 and A.sub.3 denote hydrogen, halogen, --CN, --NO.sub.2, C.sub.1 -C.sub.6 -alkyl, cycloalkyl, C.sub.1 -C.sub.18 -alkoxy, optionally substituted phenoxy, optionally substituted C.sub.1 -C.sub.18 -alkylsulphonyl, optionally substituted phenylsulphonyl, optionally substituted sulphamoyl, optionally substituted carbamoyl, optionally substituted phenylazo, C.sub.1 -C.sub.18 -alkoxycarbonyl, --CF.sub.3, --SCN, C.sub.1 -C.sub.12 -alkylmercapto, C.sub.1 -C.sub.6 -alkylcarbonyl, optionally substituted phenylcarbonyl or --OH,A.sub.4 and A.sub.5 denote hydrogen, halogen, optionally substituted C.sub.1 -C.sub.6 -alkyl, optionally substituted C.sub.1 -C.sub.6 -alkoxy, --NH--CO--CH.sub.2 CH.sub.2 OA.sub.8, --NH--CO--A.sub.8, --NH--SO.sub.2 --A.sub.
    Type: Grant
    Filed: August 4, 1986
    Date of Patent: October 11, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Manfred Lorenz, Rainer Hamprecht, Artur Haus
  • Patent number: 4775223
    Abstract: An optically active lactic acid derivative represented by the following formula (I): ##STR1## wherein R is a saturated or unsaturated hydrocarbon group of a linear, branched or cyclic structure having 4 to 20 carbon atoms; Ra is --CO--Rb or --CH.sub.2 --Rc wherein Rb is a releasable chemically active group, and Rc is a releasable chemically active group; and C with * represents an asymmetric carbon atom.
    Type: Grant
    Filed: September 17, 1985
    Date of Patent: October 4, 1988
    Assignee: Canon Kabushiki Kaisha
    Inventors: Kazuo Yoshinaga, Kazuharu Katagiri
  • Patent number: 4771129
    Abstract: An azo compound of the formula: ##STR1## wherein M.sub.1, M.sub.2 and M.sub.3 are, the same or different, each a hydrogen atom, an alkali metal atom, an ammonium group or an organic ammonium group; R.sub.1 and R.sub.2 are, the same or different, each a C.sub.1 -C.sub.3 alkyl group, a C.sub.1 -C.sub.3 alkoxy group, a halogen atom or a hydrogen atom; m is 1 or 2; and X and Y are, the same or different, each a C.sub.6 -C.sub.18 alkylamine, alkoxyalkylamine, arylamine, aralkylamine, alkanolamine or alkarylamine residue, which is useful as a magenta color dyestuff for an aqueous ink composition, particularly for ink jet recording.
    Type: Grant
    Filed: March 13, 1986
    Date of Patent: September 13, 1988
    Assignees: Taoka Chemical Company, Limited, Sumitomo Chemical Company, Limited
    Inventors: Hideo Kawashita, Mitsuhiro Ota
  • Patent number: 4769449
    Abstract: Azo dyes of the formula ##STR1## wherein R.sup.1 is alkyl having 1 to 4 carbon atoms; R.sup.2 is alkyl having 1 to 3 carbon atoms; R.sup.3 is alkylcarbonyloxyethyl having 1 to 3 carbon atoms in the alkyl moiety, alkoxycarbonyloxyethyl having 1 to 4 carbon atoms in the alkoxy moiety, methoxyethoxycarbonyloxyethyl or ethoxyethoxycarbonyloxyethyl; and R.sup.4 is one of the definitions of R.sup.3 or cyanoethyl; or mixtures of at least two species of said formula are used for dyeing and printing hydrophobic fiber materials.
    Type: Grant
    Filed: February 5, 1987
    Date of Patent: September 6, 1988
    Assignee: Cassella Aktiengesellschaft
    Inventors: Ulrich Buhler, Manfred Hahnke, Michael Kunze, Albert Bode
  • Patent number: 4767844
    Abstract: An azo lake pigment is obtained by coupling an aromatic diazo component having a sulfonic acid group with a mixture of 2-hydroxy-3-naphthoic acid and a 2-hydroxy-3-naphthoic acid derivative represented by formula [I] ##STR1## wherein R represents a hydrogen atom, a naphthalene residue, a cyclohexyl group, or a group of the formula ##STR2## in which each of X, Y and Z represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom, an acetylamino group, a benzoylamino group, a carbomoyl group or a phenylcarbamoyl group, and X and Y together may form a cyclized benzimidazolone, benzthiazole or benzoxazole group,and laking the resulting dye with an alkaline earth metal salt or a manganese salt.
    Type: Grant
    Filed: August 21, 1987
    Date of Patent: August 30, 1988
    Assignee: Dainippon Ink and Chemicals, Inc.
    Inventors: Hirohito Ando, Zenji Takada, Shigeto Aoki, Yuko Shigeta
  • Patent number: 4764599
    Abstract: Sulfo-free compounds of the formula ##STR1## where R is hydrogen or C.sub.1 -C.sub.4 -alkyl andK.sup.1 and K.sup.2 independently of one another are a radical of a coupling component, and the rings A and B may furthermore be monosubstituted or polysubstituted by fluorine, chlorine, bromine, nitro, methyl, trifluoromethyl, ethyl, acetyl, benzoyl, a carboxylic ester group, unsubstituted or substituted carbamyl or sulfamyl, an aryl sulfonate group, C.sub.1 -C.sub.4 -alkylsulfonyl, unsubstituted or substituted phenylsulfonyl, cyano or acylamino or a fused ring, are very useful as pigments for coloring printing inks, surface coatings or plastics.
    Type: Grant
    Filed: September 30, 1986
    Date of Patent: August 16, 1988
    Assignee: BASF Aktiengesellschaft
    Inventors: Horst Colberg, Erwin Hahn
  • Patent number: 4758659
    Abstract: A hexakisazo dye suitable for dyeing cellulose, natural or synthetic polyamide meterials, leather, represented by the formula ##STR1## wherein X is --CH.dbd.CH--, --CONH--, --CRH-- (wherein R is phenyl which is unsubstituted or substituted by H or a sulfonic acid group), -SO.sub.2 -- or --O--; Y is H, CH.sub.3 OCH.sub.3, Cl or SO.sub.3 M; A.sub.1 and A.sub.2 are each ##STR2## (wherein Z.sub.1 is H, Cl, CH.sub.3, OH, OCH.sub.3, OC.sub.2 H.sub.5 or SO.sub.3 M, and Z.sub.2 is H, CH.sub.3, NO.sub.2 or COOM); B.sub.1 and B.sub.2 are each ##STR3## (wherein Z.sub.3 is H, OH, NH.sub.2 Cl or COOM, Z.sub.4 is H, Cl, CH.sub.3, OH OCH.sub.3, NH.sub.2, COOM or SO.sub.3 M, and Z.sub.5 is H, C.sub.1 -C.sub.4 alkyl or OH); M is H, Na, K, Li or NH.sub.4 ; f is 0 or 1; m is 0, 1 or 2; and n is 0, 1 or 2.
    Type: Grant
    Filed: July 29, 1986
    Date of Patent: July 19, 1988
    Assignee: Orient Chemical Industries, Ltd.
    Inventors: Hisashi Senshu, Sadahiko Matsubara, Tamotsu Naito
  • Patent number: 4754024
    Abstract: The invention relates to reactive dyes of the formula ##STR1## wherein D is the radical of a diazo component, R.sub.1 and R.sub.2 are each independently an unsubstituted or substituted alkyl or alkenyl group, Y is a --CH.dbd.CH.sub.2 or --CH.sub.2 CH.sub.2 --X radical in which X is a fibre-reactive radical, and the benzene ring A may be further substituted. These dyes are suitable for dyeing and printing textile fibre material and yield dyeings and prints of good fastness properties.
    Type: Grant
    Filed: August 25, 1986
    Date of Patent: June 28, 1988
    Inventor: Hansrudolf Schwander
  • Patent number: 4751288
    Abstract: The compounds of the formula I ##STR1## where R is unsubstituted or substituted phenyl or naphthyl, R.sup.1 and R.sup.2 are each unsubstituted or substituted alkyl, alkenyl or cycloalkyl, and one of the radicals may furthermore be hydrogen, R.sup.3 is hydrogen, methyl, methoxy, ethoxy or chlorine, and R.sup.4 is acylamino, are particularly useful for dyeing polyesters.
    Type: Grant
    Filed: March 24, 1986
    Date of Patent: June 14, 1988
    Assignee: BASF Aktiengesellschaft
    Inventors: Udo Bergmann, Erwin Hahn, Guenter Hansen, Helmut Reichelt
  • Patent number: 4739042
    Abstract: Halftone gravure printing inks containing pyridone azo dyestuffs wherein the dyestuffs are obtained by reacting a pyridone dyestuff of the formula ##STR1## with a dicarboxylic or polycarboxylic acid or a pyridone azo dyestuff of the formula ##STR2## with a dihydroxy or polyhydroxy compound.
    Type: Grant
    Filed: August 4, 1986
    Date of Patent: April 19, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Manfred Lorenz, Artur Haus
  • Patent number: 4737240
    Abstract: Black trisazo dyes for cellulosic textiles, leather and especially paper having the structure ##STR1## where A is ##STR2## one of B.sub.1 and B.sub.2 is hydrogen and the other is --SO.sub.3 M or a mixture thereof, and M is hydrogen, sodium, potassium, lithium or --HNR.sub.1 R.sub.2 R.sub.3 wherein R.sub.1, R.sub.2 and R.sub.3 represent the same or different substituents selected from hydrogen, lower alkyl and lower hydroxyalkyl, and stable liquid concentrates of these dyes are described.
    Type: Grant
    Filed: June 27, 1986
    Date of Patent: April 12, 1988
    Assignee: Ciba-Geigy Corporation
    Inventors: Herbert S. Davis, Roy E. Smith, Mortimer Weiser
  • Patent number: 4721779
    Abstract: Trisazo compounds of the formula ##STR1## where Z is ##STR2## X and Y independently of one another are each C.sub.1 -C.sub.24 -alkoxy, benzyloxy, phenylethoxy, mono-C.sub.1 -C.sub.24 -alkylamino, monobenzylamino, monophenylethylamino, monophenylamino, bis-C.sub.1 -C.sub.24 -alkylamino, N-C.sub.1 -C.sub.12 -alkyl-N-benzylamino, N-C.sub.1 -C.sub.12 -alkyl-N-phenylethylamino or N-C.sub.1 -C.sub.12 -alkyl-N-phenylamino, where the benzene rings are unsubstituted or substituted by C.sub.1 -C.sub.12 -alkyl, cyclohexyl, 4-C.sub.1 -C.sub.12 -alkylcyclohexyl, C.sub.1 -C.sub.24 -alkoxy, phenoxy or C.sub.1 -C.sub.24 -alkanoyloxy, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 independently of one another are each hydrogen, methyl, methoxy, or chlorine and R.sup.7 is hydrogen or methyl, and the ring A or B may furthermore carry a fused benzene ring, are very useful as dyes in liquid crystal media, for example for electrooptical displays.
    Type: Grant
    Filed: August 5, 1986
    Date of Patent: January 26, 1988
    Assignee: BASF Aktiengesellschaft
    Inventor: Karl-Heinz Etzbach
  • Patent number: 4704452
    Abstract: Monoazo compounds of the formula ##STR1## in which one of the two substituents R.sub.1 or R.sub.2 or both substituents are C.sub.3 -C.sub.8 -alkyl or a group of the formula ##STR2## in which R.sub.3 and R.sub.4 are independently of each other hydrogen or C.sub.1 -C.sub.4 -alkyl and R.sub.5 is hydrogen, halogen or C.sub.1 -C.sub.4 -alkyl and the other of the two substitutents R.sub.1 or R.sub.2, when the two are not C.sub.3 -C.sub.8 -alkyl or a group of the formula (1a), is hydrogen, halogen or C.sub.1 -C.sub.4 -alkyl, and KK is the radical of a coupling component which is free of water-solubilizing groups the two described. These compounds can be used as dyes for dyeing or printing for example polyester fibre materials.
    Type: Grant
    Filed: December 19, 1985
    Date of Patent: November 3, 1987
    Assignee: Ciba-Geigy Corporation
    Inventor: Peter Liechti
  • Patent number: 4701525
    Abstract: Compounds of the formula(B--L.sub.m --A--L'--B'.sub.n, (1)in which A is the radical of a bisazo or trisazo dye, L and L' are organic radicals and B and B' are cyclic organic radicals and at least one of the radicals B and B' has spectral absorption in the UV region and one of the radicals B and B' is different from 2,4-dihydroxyphenyl, m is 1 or 2 and n is 0, 1 or 2.The compounds are suitable for use as image dyes in photographic silver dye bleach materials.
    Type: Grant
    Filed: June 2, 1986
    Date of Patent: October 20, 1987
    Assignee: Ciba-Geigy AG
    Inventors: Thomas-Markus Rohr, Jakob Kuhn
  • Patent number: 4687842
    Abstract: Compounds of the formula ##STR1## wherein each of R and R.sub.1 is independently hydrogen, C.sub.1-4 alkyl, phenyl or phenyl substituted by 1 to 3 C.sub.1-4 alkyl, C.sub.1-4 alkoxy or halo substitutents orR and R.sub.1 taken together are trimethylene or tetramethylene,each of R.sub.2 and R.sub.3 is independently allyl, C.sub.1-4 alkyl, phenyl (C.sub.1-4 alkyl) or C.sub.2-4 alkyl monosubstituted by hydroxy, cyano or carbamoyl, ##STR2## wherein R.sub.5, R.sub.6, R.sub.7 and R.sub.8 are as defined in the specification, andA.sup..crclbar. is an anion, and mixtures thereof with cationic 5-hydroxypyrazole dyes, are useful for dyeing and printing materials dyeable with basic dyes, e.g., homopolymers and copolymers of acrylonitrile and asymmetrical dicyanoethylene, polyamides and polyesters modified to contain acidic groups, leather and paper.
    Type: Grant
    Filed: January 14, 1980
    Date of Patent: August 18, 1987
    Assignee: Sandoz Ltd.
    Inventor: Beat Henzi
  • Patent number: 4677200
    Abstract: The invention relates to aminoazo compounds of the formula I ##STR1## in which X and Y are identical or different and denote hydrogen, chlorine, bromine, methyl, methoxy, ethoxy, nitro, trifluoromethyl, carbomethoxy or carboethoxy, A represents hydrogen, methyl or ethyl, and Z in the 6- or 7-position of the heteroaromatic ring system is hydrogen, chlorine or bromine, methyl, methoxy, ethoxy, carbomethoxy, carboethoxy or nitro.The compounds of the formula I are prepared by coupling a monodiazotized p-diaminobenzene substituted by X and Y analogously to the formula I with a 5-acetoacetylaminobenzimidazolone which carries the radicals A and Z analogously to the formula I. In the case where X, Y or Z does not denote a nitro group, it is possible to use in place of the p-diaminobenzene derivative a p-aminonitrobenzene derivative which is disubstituted by X and Y in the 2- and 5-positions.
    Type: Grant
    Filed: April 3, 1985
    Date of Patent: June 30, 1987
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Klaus Hunger
  • Patent number: 4668774
    Abstract: Novel dye salts of anionic dyes of the general formula I ##STR1## where F is a radical of an anionic dye, n is 1, 2, 3 or 4, and B.sup.1 and B.sup.2 independently of one another are each unsubstituted or substituted branched alkyl or alkyl-substituted cycloalkyl having a total of 10 to 36 carbon atoms, are very useful for dyeing solvents, printing inks or polymeric film-forming materials.
    Type: Grant
    Filed: April 23, 1985
    Date of Patent: May 26, 1987
    Assignee: BASF Aktiengesellschaft
    Inventors: Hermann Loeffler, Rainer Dyllick-Brenzinger