Hetero Ring Or Polycyclo Ring System Which Contains A Hetero Ring As One Of The Cyclos Bonded Directly To An Azo Group Patents (Class 534/740)
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Publication number: 20100199443Abstract: The present invention relates to novel yellow anionic dyes, a process for their preparation, certain novel intermediates necessary for their preparation and the use of these dyes for dyeing natural or synthetic materials, in particular, paper. The dyes are of formula (14), (15) or (16) in which R1 represents hydrogen, C1-C4alkyl, C1-C4alkoxy or SO3H, R2 represents SO3H or CO2H, R3 represents hydrogen, C1-C4alkyl, halogen, hydroxy, C1-C4alkoxy, carboxy, NH2 or NHC1-C4alkyl, R3a represents hydrogen or NH2 and A1 and A2, independently of the other, is selected from the group consisting of an acetoacetylated amine, a derivative of barbituric acid, a 2,4,6-triaminopyrimidine derivative, a pyridone derivative, an aminopyrazole or a pyrazolone derivative and a benzoic acid derivative, or A1 and A2, each one independently of the other, represent a certain phenol residue.Type: ApplicationFiled: March 29, 2010Publication date: August 12, 2010Inventors: Michael Lennartz, Adolf Kåser, Sandra Weiss
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Patent number: 7341607Abstract: The present invention relates to novel yellow anionic dyes, a process for their preparation, certain novel intermediates for their preparation and the use of these dyes for dyeing natural or synthetic materials, in particular, paper.Type: GrantFiled: May 27, 2003Date of Patent: March 11, 2008Assignee: Ciba Specialty Chemicals Corp.Inventors: Michael Lennartz, Adolf Käser, Sandra Weiss
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Patent number: 7262284Abstract: A method for the production of a diazo pigment, or a mixture of diazo pigments, according to formula (I) of the specification by azo coupling, wherein the azo coupling product is subjected to a finish in an organic solvent or in an agueous organic solvent with a neutral or alkaline pH.Type: GrantFiled: May 27, 2003Date of Patent: August 28, 2007Assignee: Clariant Produkte (Deutschland) GmbHInventors: Olaf Schupp, Felix W. Grimm, Manfred Opravil, Joachim Weber
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Patent number: 7144993Abstract: The present invention relates to a process for the preparation of a compound of the general formula (I), which comprises converting a compound of the general formula (II), in an aprotic organic solvent in the presence of a catalytically active amount of a strong acid (catalyst) or of an agent that liberates a strong acid or of an ammonium salt of a strong acid, it also being possible for the catalyst to be part of the starting material/product, into a compound of formula I, wherein R5, R6 and R8 are each independently of the others a hydrogen atom, a nitro group, a sulfo group, a halogen atom, a pseudohalogen, a group COOR1 or CONHR2 or a C1-8 alkyl, C1-8 alkoxy or aryloxy radical, an amide group, a thioalkyl or thioaryl radical, an alkyl- or aryl-sulfonyl radical, an alkyl- or aryl-sulfinyl radical, a trifluoromethyl group or a phosphono group, R1 and R2 being a hydrogen atom or a C1-8 alkyl radical or an aryl or aralkyl radical, R10 is a group —C(O)CH2C(O)CH3 and R11 is a hydrogen atom or an acyl radical, oType: GrantFiled: December 3, 2002Date of Patent: December 5, 2006Assignee: Ciba Specialty Chemicals Corp.Inventors: Johannes Benkhoff, Bernd Lamatsch
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Patent number: 6756487Abstract: Monoazoquilolone pigments which, in one of the tautomeric forms thereof, correspond to formula (1), wherein Ar is a radical of formula (2a), (2b), (2c), (2d), 2(e) or (2f) wherein R1 is C1-C4alkyl, R2 and R3 are each independently of the other hydrogen, halogen, C1-C4alkyl, carboxy, sulfo, cyano, C1-C4alkoxycarbonal, C1-C4alkylcarbonyl, C1-C4alkanoylamino, benzoylamino that is unsubstituted or substituted in the phenyl ring by halogen, nitro, C1-C4alkyl or by C1 -C4alkoxy; carbamoyl, N-C1-C4alkylaminocarbonyl, N-arylaminocarbonyl that is unsubstituted or substituted in the aryl moiety by halogen, nitro, C1-C4alkyl or by C1-C4alkoxy; N,N-di-C1-C4alkylaminocarbonyl, C1-C4alkoxysulfonyl, C1-C4alkylsulfonyl, sulfamoyl, N-C1-C4alkylaminosulfonyl, N-arylaminosulfonyl that is unsubstituted or substituted in the aryl moiety by halogen, nitro, C1-C4alkyl or by C1-C4alkoxy; or N,N-di-C1-C4alkylaminosulfonyl, wherein carboxy and sulfo are in the form of the free acid or in salt form, R8and R9are each independently of thType: GrantFiled: September 2, 2003Date of Patent: June 29, 2004Assignee: Ciba Specialty Chemicals CorporationInventors: Johannes Benkhoff, Olof Wallquist, Tetsuo Hyuga, Gerardus De Keyzer
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Patent number: 5559216Abstract: An ecologically and economically advantageous process for preparing a disazo pigment of the formula (I) or a mixture of said disazo pigments ##STR1## where D.sup.1 and D.sup.2 are identical or different and each is unsubstituted phenyl, phenyl with from 1 to 5 substituents, unsubstituted naphthyl, naphthyl with from 1 to 3 substituents, unsubstituted anthraquinonyl, anthraquinonyl with from 1 to 3 substituents, or a radical of a fused aromatic heterocycle which contains from 1 to 3 identical or different heteroatoms from nitrogen or oxygen and sulfur and is unsubstituted or has from 1 to 3 substituents,R.sup.1 and R.sup.2 are identical or different and each is hydrogen, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.Type: GrantFiled: September 1, 1993Date of Patent: September 24, 1996Assignee: Hoechst AGInventors: Ruediger Jung, Joachim Weide, Hans J. Metz
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Patent number: 5554736Abstract: The invention provides a process for the production of azodyes and their derivatives by diazotization and coupling reactions and optionally further modification reactions, wherein a compound of formula ##STR1## in which E signifies an aromatic bivalent radical,X.sub.1 signifies hydroxy or a primary amino group,Y.sub.1 signifies hydroxy or a primary amino groupand in which the aminogroup linked to the --SO.sub.2 -bound phenyl radical may optionally be acylated,or a mixture of compounds of formula (I), is employed as a coupling component or/and--in the non-acylated form--as a diazo component,the invention in particular relates also to the novel dyes and their use and to the novel intermediates.Type: GrantFiled: June 6, 1995Date of Patent: September 10, 1996Inventors: Jordi B. Barra, Jose R. Sorolla
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Patent number: 5037966Abstract: Dyes of the formula ##STR1## where R and R.sub.1 are independently of the other hydrogen, halogen, nitro, alkyl or alkoxy and KK is the radical of a coupling component, which are particularly suitable for dyeing polyester fibers if no water-solubilizing group is present, and which are particularly suitable for dyeing and printing textile materials made of polyamide fibers when at least one sulfo group is present in the dye.Type: GrantFiled: February 28, 1990Date of Patent: August 6, 1991Assignee: Ciba-Geigy CorporationInventor: Rudolf Naef
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Patent number: 4997920Abstract: Compounds of the formulae I and II ##STR1## in which A is a radical of the formulae III, IV or V ##STR2## R.sub.1 and R.sub.4 are --H or --Cl, R.sub.2 and R.sub.5 are --H, halogen, --NO.sub.2, --CN, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 alkoxy, --CF.sub.3 or phenyloxy which is unsubstituted or substituted by one or two chlorine atoms and/or one or two methyl or methoxy groups, and R.sub.3 is alkyl having at least 10 C atoms, X is a radical of the formulae --NH--, --O--, ##STR3## n is the number 1 or 2, Y is the radical of the formulae --COO--, --OOC--, --CONH-- or --NHCO-- or a radical of the formulae ##STR4## in which R.sub.1 and R.sub.2 are as defined above, D is an aromatic heterocyclic 5- or 6-membered ring, in which the ring contains 1 or 2 N atoms and may additionally contain an O atom or S atom, Z is --H, --Br, --OCH.sub.3, --CN or --NO.sub.2 and X.sub.1 and X.sub.2, independently of one another, are --H, halogen, --CH.sub.3, --OCH.sub.3, --OC.sub.2 H.sub.5 or --NO.sub.2 and X.sub.Type: GrantFiled: September 11, 1989Date of Patent: March 5, 1991Assignee: Ciba-Geigy CorporationInventors: Stefan Hari, Olof Wallquist, Jost von der Crone
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Patent number: 4981489Abstract: 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 or 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 subtsituted 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: GrantFiled: October 23, 1989Date of Patent: January 1, 1991Assignee: BASF Lacke & Farben AktiengesellschaftInventors: Wolfgang Ruff, Egon Liedek, Gerhard Berger, Hans W. Sonneborn
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Patent number: 4968352Abstract: Diaryl pigments having excellent dried ink transparency and improved process heat stability are prepared by carrying out the coupling of a bisdiazotized substituted 4,4' diaminobiphenyl with acetoacetanilides and/or pyrazolinones in the presence of an added quantity of one or more substituted aromatic amines containing at least one sulfonic or carboxylic acid substituent, or their salts. The pigments exhibit improved tolerance to variations in drying temperatures and to high drying temperatures, and have improved transparency when present in dried ink formulations.Type: GrantFiled: April 28, 1988Date of Patent: November 6, 1990Assignee: Hoechst Celanese CorporationInventors: Boyd A. Keys, John T. Ouderkirk
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Patent number: 4952681Abstract: 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: GrantFiled: July 27, 1988Date of Patent: August 28, 1990Assignee: Sandoz AGInventors: Guenter Hansen, Ernst Schefczik, Karl-Heinz Etzbach, Helmut Reichelt, Hermann Loeffler
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Patent number: 4946508Abstract: Disazo pyrazolone pigments are provided which have improved properties achieved by incorporating certain azomethine compounds. The pigment is prepared by reacting a primary amine terminated alkylene oxide polymer and acetoacetanilide or substituted acetoacetanilide to form an azomethine coupler, and subsequently co-reacting the azomethine coupler and a pyrazolone coupler with tetrazotized 3,3'-dichlorobenzidine or tetrazotized o-dianisidine. The pigment is useful in printing ink, plastics and paints.Type: GrantFiled: May 23, 1989Date of Patent: August 7, 1990Assignee: Sun Chemical CorporationInventors: Russell J. Schwartz, Manuel Z. Gregorio
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Patent number: 4946509Abstract: Diarylide pigments modified with alkylene oxide polymers. The modified pigments are useful in both water-based and solvent-based coating and ink compositions.Type: GrantFiled: May 23, 1989Date of Patent: August 7, 1990Assignee: Sun Chemical CorporationInventors: Russell J. Schwartz, Manuel Z. Gregorio, Anthony C. Zwirgzdas
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Patent number: 4906740Abstract: The present invention relates to monoazo dyes which dye polyamide material with good light- and wet-fastness and which have the formula ##STR1## in which K is the radical of an amino- or alkoxy-benzene, amino- or alkoxy-naphthalene, naphthol, aminonaphthol, pyrazolone, aminopyrazole, indole, naphthimidazole, diphenylamine, tetrahydroquinoline or acetoacetamide and can be further substituted, R is hydrogen, halogen, C.sub.1-6 -alkyl, trifluoromethyl, carboxyl or a --SO.sub.2 --C.sub.1-6 --alkyl, --SO.sub.2 --R.sub.1, ##STR2## --CO--R.sub.4 group, in which R.sub.1 is a substituted or unsubstituted phenyl- or naphthyl-C.sub.1-4 -alkyl radical, R.sub.2 and R.sub.3 independently of one another are hydrogen or a substituted or unsubstituted C.sub.1-6 -alkyl or C.sub.5-7 -cycloalkyl radical and R.sub.4 is a substituted or unsubstituted phenyl radical, and X is hydrogen, C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy or halogen, and in which R in formula (1) may not be hydrogen or chlorine if the radical --N.dbd.Type: GrantFiled: July 15, 1986Date of Patent: March 6, 1990Assignee: Ciba-Geigy CorporationInventor: Rudolf Hurter
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Patent number: 4780533Abstract: A disazo pigment is prepared by coupling the tetrazo compound of 3,3'-dichlorobenzidine with an acetoacetanilide compound which is other than those represented by the below-described general formula (I) and is free of water-soluble groups. In the present invention, about 0.5-50 mole % of the acetoacetanilide compound is replaced by a compound represented by the following general formula (I): ##STR1## wherein R means a methyl, ethyl, propyl or butyl group or a substituted or unsubstituted phenyl group.Type: GrantFiled: February 9, 1987Date of Patent: October 25, 1988Assignee: Dainichiseika Color & Chemicals Mfg. Co., Ltd.Inventors: Naonori Takami, Tetsuo Fukuda, Takeshi Uehara
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Patent number: 4764599Abstract: 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: GrantFiled: September 30, 1986Date of Patent: August 16, 1988Assignee: BASF AktiengesellschaftInventors: Horst Colberg, Erwin Hahn
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Patent number: 4685934Abstract: Monoazo compounds of formula ##STR1## wherein R.sub.1 is a coupling component radical,R.sub.1 is C.sub.1-6 alkyl; C.sub.1-6 alkyl substituted by 1 or 2 substituents selected from chloro, cyano, hydroxy, C.sub.1-4 alkoxy, phenyl and phenyl substituted by 1 or 2 substituents selected from chloro, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, carboxy, sulfo, sulfamoyl and acetamido; C.sub.5-7 cycloalkyl; C.sub.5-7 cycloalkyl substituted by 1 to 3 C.sub.1-4 alkyl groups; phenyl; phenyl substituted by 1 to 3 substituents selected from chloro, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, acetamido (maximum of 1), carboxy (maximum of 1), sulfo (maximum of 1) and --SO.sub.2 NR.sub.7 R.sub.8 (maximum of 1); 1- or 2-naphthyl or 1- or 2-naphthyl substituted by sulfo,whereineach of R.sub.7 and R.sub.8 is independently hydrogen; C.sub.1-4 alkyl; C.sub.1-4 alkyl monosubstituted by hydroxy or phenyl; cyclohexyl; phenyl or phenyl monosubstituted by chloro, methyl or methoxy, or--NR.sub.7 R.sub.Type: GrantFiled: July 12, 1985Date of Patent: August 11, 1987Assignee: Sandoz Ltd.Inventors: Francois Benguerel, Roland Mislin
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Patent number: 4686285Abstract: (i) Metal-free compounds of the formula ##STR1## (ii) tautomers thereof, (iii) 1:1 and 1:2 metal complexes of (i) and (ii),(iv) salts of (i), (ii), and (iii), and(v) mixtures of (i), (ii), (iii), and (iv),wherein the symbols are as defined in the Specification, are useful as dyes for, for example, polymers and copolymers of acrylonitrile, polyesters modified to contain acid groups, polyamides such as wool, leather, cotton, bast fibers such as hemp, flax, sisal jute, coir and straw, regenerated cellulose, glass fibers and paper (those wherein R.sub.o is other than hydrogen) or as intermediates for the synthesis of dyes.Type: GrantFiled: February 8, 1985Date of Patent: August 11, 1987Assignee: Sandoz Ltd.Inventor: Reinhard Pedrazzi
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Patent number: 4634764Abstract: Compounds of the formula ##STR1## wherein each R is independently --N(R.sub.1).sub.2, --N.sup..sym. (R.sub.2).sub.3 A.sup..crclbar. or hydroxy, whereineach R.sub.1 is independently hydrogen, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl or aryl orboth R.sub.1 's taken together and with the nitrogen atom to which they are attached form a 5- or 6-membered saturated heterocyclic ring,each R.sub.2 is independently alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl or aryl ortwo R.sub.2 's taken together and with the nitrogen atom to which they are attached form a 5- or 6-membered saturated heterocyclic ring orall three R.sub.2 's taken together and with the nitrogen atom to which they are attached form a 5- or 6-membered unsaturated heterocyclic ring, andA.sup..crclbar. is a non-chromophoric anion,each T is independently a bridging radical, andZ is hydrogen or --N.dbd.Type: GrantFiled: November 10, 1983Date of Patent: January 6, 1987Assignee: Sandoz Ltd.Inventor: Manfred Greve
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Patent number: 4623720Abstract: 1:1 and 1:2 metal complexes comprising the unit of the formula ##STR1## wherein A and B, independently, are radicals of diazo or coupling components, with the proviso that when one of A and B is a radical of a diazo component, the other is a radical of a coupling component,T is --SO.sub.2 N(R.sub.1)-- or --N(R.sub.1)SO.sub.2 --, wherein R.sub.1 is hydrogen, C.sub.1-4 alkyl, C.sub.1-4 alkyl substituted by phenyl or carboxy or C.sub.2-4 alkyl substituted in the .beta.--, .gamma.-- or .delta.--position by phenoxy, C.sub.1-4 alkyl, chloro or hydroxy, with the proviso that T is --N(R.sub.1)SO.sub.2 -- when A is the radical of a diazo component and T is --SO.sub.2 N(R.sub.Type: GrantFiled: June 4, 1981Date of Patent: November 18, 1986Assignee: Sandoz Ltd.Inventor: Herbert Holliger
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Patent number: 4600674Abstract: Disclosed is an electrophotographic photoconductive material excellent in sensitivity and durability which comprises an electroconductive substrate and, provided thereon, a photosensitive layer containing a trisazo pigment represented by the general formula ##STR1## wherein R's, which may be the same or different, represent each a hydrogen atom, halogen atom, substituted or unsubstituted alkyl group, alkoxyl group, or nitrile group; n is an integer of 1 or 2; and A represents ##STR2## wherein Z represents a group of atoms necessary to complete a substituted or unsubstituted aromatic carbon ring or a substituted or unsubstituted aromatic hetero-ring; X represents a hydrogen atom, an alkyl group, or a group of atoms necessary to complete a substituted or unsubstituted aromatic carbon ring, a substituted or unsubstituted aromatic hetero ring, or a substituted or unsubstituted hetero ring; m is 0 or 1; B represents a group of atoms necessary to complete a substituted or unsubstituted aromatic carbon ring, a substType: GrantFiled: June 24, 1985Date of Patent: July 15, 1986Assignee: Mitsubishi Paper Mills, Ltd.Inventors: Kazuhiro Emoto, Akira Itoh
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Patent number: 4579939Abstract: Yellow dyes from substituted 2-aminothiophene and acyclic active methylene coupling components are of particular interest for dyeing polyester fibers. The dyes have the formula: ##STR1## wherein: X is a group such as alkyl, allyloxy, alkoxy, aryl or the like; Y is hydrogen, alkyl, or aryl; Z is alkyl, aryl, alkylsulfonyl, cyano or COX where X is defined above; R is cyano, carbamyl, alkanoyl, aroyl, or the like; R.sub.1 is selected from the R groups and ##STR2## wherein R.sub.2 represents the atoms necessary to complete an azole radial selected from benzothiazole, benzimidazole, benzoxazole, 1,3,4-oxadiazole, 1,3,4-thiadiazole, and pyrazole; and wherein the hydrocarbon moieties of each of the above radicals or groups may be substituted with up to three of --OH, alkoxy, hydroxyalkoxy, alkylcarbamyl, or the like.Type: GrantFiled: March 16, 1984Date of Patent: April 1, 1986Assignee: Eastman Kodak CompanyInventors: Max A. Weaver, Clarence A. Coates, Jr.
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Patent number: 4568738Abstract: Thiophen-2-ylazopyrazole dyes useful for dyeing polyesters, cellulose acetate esters, and polyamides in fast yellow shades have the general formula: ##STR1## wherein: X is alkyl, allyloxy, alkoxy, aryl, aryloxy, amino, alkylamino, arylamino, cyclohexyloxy,, thienyl, cycloalkylamino, N,N-dialkylamino, or N-alkyl-N-arylamino; Y is hydrogen, alkyl, or aryl; Z is alkyl, aryl, alkylsulfonyl, 2-benzothiazolyl, cyano or COX; R and R.sub.1 are alkyl or aryl; R.sub.2 is hydrogen, alkyl, aryl, acyl, benzothiazolyl, pyridyl, sulfolanyl, quinolyl, thiocarbamyl, carbamyl, alkoxycarbonyl, aroyl, aryl-carbamyl and alkanoyl; and wherein the hydrocarbon moieties of the above radicals may be substituted with up to three of --OH, alkoxy, hydroxyalkoxy, carbamyl, and similar groups conventionally used in the azo dye art.Type: GrantFiled: March 19, 1984Date of Patent: February 4, 1986Assignee: Eastman Kodak CompanyInventors: Max A. Weaver, Clarence A. Coates, Jr.
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Patent number: 4562247Abstract: There are described azo compounds of the formula ##STR1## wherein D.sub.1 and D.sub.2 are each the radical of a diazo component, R is C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 alkyl substituted by C.sub.1 -C.sub.4 -alkoxy or halogen or is phenyl or phenyl substituted by C.sub.1 -C.sub.4 -alkyl, halogen or C.sub.1 -C.sub.4 alkoxy, and Y is a basic or cationic group. These azo compounds can be used as dyes for dyeing and printing natural and synthetic, cationically dyeing substrates, particularly textile materials and paper.Type: GrantFiled: May 29, 1984Date of Patent: December 31, 1985Assignee: Ciba Geigy CorporationInventor: Visvanathan Ramanathan