Amine Salt Patents (Class 534/693)
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Publication number: 20100119764Abstract: To provide an optical recording medium on which recording/retrieving of high density optical information is possible by a short wavelength light such as a blue laser. An optical recording medium comprising a substrate and a recording layer capable of recording or retrieving information by irradiation with light, formed on the substrate, wherein the recording layer contains the cyanine dye represented by the following formula (I): wherein each of A1 and B1 which are independent of each other, is an aromatic ring which may have a substituent, provided that at least one aromatic ring of A1 and B1 contains a nitrogen atom; each of R1 and R2 which are independent of each other, is a substituent, provided that R1 and/or R2 may be bonded to other cation; each of X1, X2, X3 and X4 which are independent of one another, is an organic group, provided that a pair of X1 and X2, and/or a pair of X3 and X4, may be mutually bonded to form a cyclic structure; Y1 is a hydrogen atom or an organic group; and Z is an anion.Type: ApplicationFiled: February 13, 2008Publication date: May 13, 2010Applicants: Mitsubishi Kagaku Media Co., Ltd., KAB. KAISHA HAYASHIBARA SEIBUTSU KAGAKU KENKYUJOInventors: Hisashi Shoda, Naoyuki Uchida, Shigeyuki Furomoto, Yasushi Aizawa, Yasufumi Dan-OH, Masahiko Toki
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Patent number: 7638610Abstract: A self-dispersible metal complex colorant is represented by formula 1, which has improved storage stability, may embody various colors and has improved fastness, such as light resistance, water resistance and the like: wherein each of A1 and A2 is independently a moiety which includes a substituted or unsubstituted C2-C30 alkenylene group having at least one double bond and is conjugated with an azo group; each of X1 and X2 is selected from the group consisting of a hydroxy group, a C1-C4 alkoxy group, a carboxyl group, and a substituted or unsubstituted amino group; M is a polyvalent transition metal; L is a neutral or anionic ligand; T is a mono- or poly-substituted hydrophilic functional group; n is an integer between 1 and 3; and J is a linker. The self-dispersible metal complex colorant may be used in various fields employing colors, such as fibers, foods, drugs, cosmetics, coatings, inks or ceramics.Type: GrantFiled: August 6, 2004Date of Patent: December 29, 2009Assignee: Samsung Electronics Co., Ltd.Inventors: Kyung-hoon Lee, Seung-min Ryu, Yeon-kyoung Jung
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Patent number: 7364597Abstract: A metal complex colorant represented by formula 1 may embody various colors and has improved fastness, such as light resistance, water resistance and the like: wherein each of A1 and A2 is independently a moiety which includes a substituted or unsubstituted C2-C30 alkenylene group having at least one double bond and is conjugated with an azo group; each of X1 and X2 is selected from the group consisting of a hydroxy group, a C1-C4 alkoxy group, a carboxyl group, and a substituted or unsubstituted amino group; M is a polyvalent transition metal; L is a neutral or anionic ligand; n is an integer from 1 to 3; and J is a linker. The metal complex colorant may be used in various fields employing colors, such as fibers, foods, drugs, cosmetics, coatings, inks or ceramics.Type: GrantFiled: August 6, 2004Date of Patent: April 29, 2008Assignee: Samsung Electronics Co., Ltd.Inventors: Yeon-kyoung Jung, Seung-min Ryu, Kyung-hoon Lee
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Patent number: 7157563Abstract: The present invention relates to organic solvent soluble dyes. In particular, the invention relates to an organic solvent soluble metal complex azo dyes containing chelated metal atoms.Type: GrantFiled: September 23, 2004Date of Patent: January 2, 2007Assignee: United Color Manufacturing, Inc.Inventor: Michael J. Smith
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Patent number: 7132516Abstract: This invention relates to coppered azo dyestuffs containing an alkyl-, aryl or alkoxyalkyl sulfamyl group on one moiety of the molecule and an alkyl-, aryl or alkoxyalkyl ammonium sulfonate or carboxylate group on the other moiety. The invention also relates to various intermediates, to compositions and to processes for preparing the metalized dyestuffs. The compounds are particularly suited for the application in laquers, ink-jet inks and electrographic toners.Type: GrantFiled: January 29, 2003Date of Patent: November 7, 2006Assignee: Clariant Finance (BVI) LimitedInventor: Dominique Pflieger
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Patent number: 6827770Abstract: A metal chelated dyestuff for inkjet recording comprising a water soluble azo metal chelated compound formed by an azo-based compound represented by the following general formula (1) having one or more hydrophilic group per molecule and a metal element; an aqueous inkjet recording liquid comprising an aqueous medium and the aforementioned metal chelated dyestuff; and an inkjet recording method using the aforementioned recording liquid are described, wherein the heterocyclic ring containing X1 is a triazole ring or the like; and Ar1 represents naphthyl group having a chelated group.Type: GrantFiled: June 18, 2002Date of Patent: December 7, 2004Assignee: Mitsubishi Chemical CorporationInventors: Tomohiro Chino, Masahiro Yamada, Hideo Sano, Wataru Shimizu, Yuukichi Murata
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Patent number: 6755903Abstract: A metal chelated dyestuff for inkjet recording is described, which is a water soluble azo metal chelated compound formed from an azo compound represented by the following general formula (1) and a metal element and is good at the clearness of color tone, light resistance, indoor discoloring and fading property, solubility, storage stability, and the like.Type: GrantFiled: June 24, 2002Date of Patent: June 29, 2004Assignee: Mitsubishi Chemical CorporationInventors: Masahiro Yamada, Tomio Yoneyama, Tomohiro Chino
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Patent number: 6521032Abstract: Inks comprising a dye of formula (1) wherein X is hydroxy, unsubstituted or hydroxy-substituted C1-C4alkyl, vinyl or a radical —CH2—CH2—Z, wherein Z is a group removable under alkaline conditions or is C1-C24alkoxy unsubstituted or substituted in the alkyl moiety, which may further be interrupted in the alkyl moiety by oxygen; phenoxy unsubstituted or substituted in the phenyl ring; C1-C4alkylthio unsubstituted or substituted in the alkyl moiety; phenylthio unsubstituted or substituted in the phenyl ring; amino; N-mono- or N,N-di-C1-C24alkylamino unsubstituted or substituted in the alkyl moiety, which may further be interrupted in the alkyl moiety by oxygen or by a radical —NR1— in which R1 is hydrogen or unsubstituted or further substituted C1-C4alkyl; C10-C20terpeneamino; C5-C7cycloalkylamino unsubstituted or substituted in the cycloalkyl ring; phenyl- or naphthyl-amino or N—C1-C4alkyl-N-phenyl- or N—C1-C4alkyl-N-naphthyl-amino unsubstituted or suType: GrantFiled: September 25, 2000Date of Patent: February 18, 2003Assignee: Ciba Specialty Chemicals CorporationInventors: Urs Lehmann, Marcel Frick
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Publication number: 20020178517Abstract: The object of the present invention is to provide organic dye compounds which exert satisfactory optical absorption properties and thermal resistance when used in high density optical recording media. The above object is solved by specific trimethine cyanine dyes, light absorbents and optical recording media which comprise the cyanine dyes, and preparations for the cyanine dyes comprising either reacting a benzoindolium compound having a compatible leaving group with a pyrazinoimidazolium compound having a reactive methyl group; or reacting a benzoindolium compound having a reactive methyl group with a pyrazinoimidazolium compound having a compatible leaving group.Type: ApplicationFiled: October 23, 2001Publication date: December 5, 2002Inventors: Chiaki Kasada, Katsumi Orita, Kentaro Yano, Toshio Kawata, Shigeo Yasui
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Patent number: 6447981Abstract: Metallized azo thioether dyes having an azo group linking a substituted 3-hydroxypyridine nucleus to a phenyl nucleus are disclosed. The phenyl nucleus has an thioether substituent ortho to the azo group but does not have electron withdrawing substituents on the phenyl nucleus. The dyes are useful in optical recording elements.Type: GrantFiled: May 26, 1998Date of Patent: September 10, 2002Assignee: Eastman Kodak CompanyInventors: Derek D. Chapman, Csaba A. Kovacs
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Publication number: 20020028918Abstract: Disclosed are novel styryl dyes, and light absorbents, light-resistant improvers, and optical recording media, which comprise the styryl dyes. The styryl dyes exert satisfactory solubilities and relatively-high light resistance when used in high-density optical recording media.Type: ApplicationFiled: July 5, 2001Publication date: March 7, 2002Applicant: KABUSHIKI KAISHA HAYASHIBARA SEIBUTSU KAGAKU KENKYUJOInventors: Chiaki Kasada, Yoshinori Koyama, Toshio Kawata, Shigeo Yasui
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Patent number: 6132894Abstract: A compound of formula (I) or a mixture thereof ##STR1## The compounds are useful as solvent dyestuffs and exhibit high solubility in alcoholic solvents, e.g. ethanol.Type: GrantFiled: February 3, 1999Date of Patent: October 17, 2000Assignee: Clariant Finance (BVI) LimitedInventors: Bansi Lal Kaul, Dominique Pflieger
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Patent number: 5731422Abstract: Complexes of formulae I and II ##STR1## wherein the variables are as defined in the specification are useful as dyes for, for example, the mass dyeing of plastics and for lacquers.Type: GrantFiled: June 6, 1995Date of Patent: March 24, 1998Assignee: Clariant Finance (BVI) LimitedInventors: Bansi Lal Kaul, Dominique Pflieger
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Patent number: 5698683Abstract: A process for preparing a mixed aluminium-heavy metal dyestuff complex, in which the amount of heavy metal present is 10-98% and that of aluminium is 2 to 90% comprisingi) reacting the metal free dyestuff with less than a stoichiometric amount of a heavy metal compound followed byii) reacting the product with an aluminium compound in an amount to produce a stoichiometric excess of metal (calculated on all the metal present) to form a mixed aluminium-heavy metal complex.Type: GrantFiled: May 12, 1995Date of Patent: December 16, 1997Assignee: Clariant Finance (BVI) LimitedInventors: Bansi Lal Kaul, Dominique Pflieger
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Patent number: 5532342Abstract: An azo metal chelate compound of an azo compound of the formula (I) with a metal: ##STR1## wherein A is a residue forming a heterocyclic ring together with the carbon atom and the nitrogen atom to which it is bonded, X is a residue forming an aromatic group together with the two carbon atoms to which it is bonded, R.sup.1 is an alkyl group which may be substituted, an aryl group which may be substituted, an alkenyl group which may be substituted, or a cycloalkyl group which may be substituted, Y is a hydrogen atom or a cation, and n is an integer of from 1 to 3.Type: GrantFiled: April 17, 1995Date of Patent: July 2, 1996Assignee: Mitsubishi Chemical CorporationInventors: Tameichi Ochiai, Yutaka Kurose, Takumi Nagao, Takako Tsukahara, Satoru Imamura
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Patent number: 5330542Abstract: A dye-incorporated composition which comprises a cyanine type dye and an azo metal chelate compound comprising an azo type compound of the following formula (I): ##STR1## (wherein A is a residue forming a hetero ring together with the carbon atom and the nitrogen atom to which it is bonded, B is a residue forming an aromatic ring or a hetero ring together with the two carbon atoms to which it is bonded, and X is a group having an active hydrogen), and a metal, and an optical recording medium comprising a recording layer which contains the dye-incorporated composition.Type: GrantFiled: January 24, 1992Date of Patent: July 19, 1994Assignee: Mitsubishi Kasei CorporationInventors: Shuichi Maeda, Satoru Imamura, Kazuo Mitsuhashi, Takako Tsukahara
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Patent number: 5298608Abstract: A metal chelate compound comprising a monoazo compound of the following formula (I): ##STR1## (wherein A is a residue forming a hetero ring together with the carbon atom and the nitrogen atom to which it is bonded, B is a residue forming an aromatic group together with the two carbon atoms to which it is bonded, and X is a hydrogen atom or a cation), and a metal, and an optical recording medium comprising a substrate and a recording layer formed thereon for information to be written in and/or read out by laser, wherein said recording layer contains the metal chelate compound comprising a monoazo compound of the above formula (I) and a metal.Type: GrantFiled: January 16, 1992Date of Patent: March 29, 1994Assignee: Mitsubishi Kasei CorporationInventors: Tetsuo Murayama, Shuichi Maeda, Chiyoko Fukabori, Takumi Nagao
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Patent number: 5204453Abstract: The invention relates to a process for the preparation of 1:2 chromium, 1:2 cobalt, 1:2 nickel or 1:2 iron complex azo dyes diazotisation, coupling and metallizing, without isolation of the coupling product, which process comprises diazotizing at least one amine of the benzene or naphthalene series in aqueous solution and coupling the diazonium compound so obtained to at least one coupling component of the benzene or naphthalene series or of the heterocyclic series, such that the azo dye obtained as intermediate contains groups suitable for metal complex formation, and carrying out the diazotization or coupling in the presence of a chromium, cobalt, nickel or iron donor.The dyes obtained by the process of the invention are suitable for dyeing in particular wool or synthetic textile polyamide fibre materials as well as leather, and for use as wood mordant dyes.Type: GrantFiled: December 30, 1991Date of Patent: April 20, 1993Assignee: Ciba-Geigy CorporationInventors: Bernard Chambon, Horst H. Jager, Rudiger Oxenius, Alois Puntener
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Patent number: 5095100Abstract: Metal complex dyes comprising a metalizable azo compound represented by one of Formulas [I] through [IV]: ##STR1## In Formulas [I] through [IV], Ps represents a phosphono group in the form of a free acid or a salt; Sf represents a sulfo group in the form of a free acid or a salt; m is 0, 1 or 2. R.sup.1 represents a hydrogen atom or an amino group; X represents a hydroxyl group, an alkoxy group having a carbon number of 1 or 2 or a carboxyl group. Y represents a hydroxyl group, an alkoxy group having a carbon number of 1 or 2, a carboxyl group or a methyl group; R.sup.2 represents a hydrogen atom or a hydroxyl group; A represents a phenyl group or naphthyl group selected from the group comprising the following 1 through 4: ##STR2## In the above formulas 1 through 4, Sf has the same definition as above; n is 0, 1 or 2. R.sup.3 represents a hydroxyl group or a carboxyl group; R.sup.4 represents a hydroxyl group, a carboxyl group or an amino group; R.sup.5 and R.sup.Type: GrantFiled: June 12, 1990Date of Patent: March 10, 1992Assignee: Orient Chemical Industries, Ltd.Inventors: Takashi Ono, Tatsuya Yagyu, Katsumi Fukuda, Minako Terasaki
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Patent number: 5008379Abstract: Water-soluble, anionic, chromium complexes of disazo compounds, at least one of the complex-forming disazo compounds being of the formula, ##STR1## in which ##STR2## is the radical of a carboxy group-containing diazo component of the benzene or naphthalene series, the carboxy group being ortho to the azo group and the diazo component being free from other metallizable groups, andB-- is the radical of a diazo component of the benzene or naphthalene series free from metallizable substituents,which complexes contain at least one water-solubilizing group, are in free acid or salt form and are useful for dyeing and printing substrates such as natural and synthetic polyamides, polyurethanes and anodized aluminum, particularly fur-lined leather.Type: GrantFiled: October 29, 1987Date of Patent: April 16, 1991Assignee: Sandoz Ltd.Inventor: Herbert Holliger
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Patent number: 4988805Abstract: The dyestuffs of the general formulae ##STR1## and salts thereof whereinX denotes hydrogen, alkoxy or NHR.sub.3,R denotes hydrogen, alkyl or alkoxy,R.sub.1 denotes alkyl,R.sub.2 and R.sub.3 denote hydrogen, alkyl, alkylcarbonyl, alkylsulphonyl, aryl, arylcar=bonyl, arylsulphonyl, aralkyl, aralkylcarbonyl or aminocarbonyl andm and n denote 1 or 2, andwherein the substituents mentioned can, in turn, be substituted by nonionic radicals or carboxylic or sulphonic acid groups customary in dyestuffs chemistry, are used for dyeing cellulose-containing materials and leather.Type: GrantFiled: July 14, 1988Date of Patent: January 29, 1991Assignee: Bayer AktiengesellschaftInventor: Klaus Kunde
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Patent number: 4874849Abstract: Dyes suitable for dyeing wool, polyamide and leather in orange, brown or olive-brown shades are disclosed, the dyes having the formula ##STR1## wherein A and D are each independently of the other a benzene or napththalene radical of a diazo component, which component carries the hydroxyl or carboxyl group in the ortho-position to the azo group;B is the radical of a coupling component which carries the group X adjacent to the azo group;X is oxygen or a radical of the formula --R--, in which R is hydrogen or C.sub.1 -C.sub.4 alkyl;Y is a radical of the formula ##STR2## in which formulae R.sup.1 and R.sup.5 are each independently of the other hydrogen or sulfo, R.sup.4 is hydrogen or nitro, R.sup.6 is hydrogen, methyl, methoxy or chlorine and R.sup.2 and R.sup.3 are each independently of the other hydrogen, halogen, nitro or sulfo;Ar.sup.1 is a benzene or napththalene radical which is unsubstituted or substituted by halogen, nitro, sulfo, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.Type: GrantFiled: December 19, 1986Date of Patent: October 17, 1989Assignee: Ciba-Geigy CorporationInventors: Gerhard Back, Fabic Beffa, Ulrich Schlesinger, Alois Puntener
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Patent number: 4853466Abstract: This invention relates to disazo dyes, and their metal complexes, which are useful for dyeing cellulosic fibers in lightfast and washfast hues. In addition, these dyes have high water solubility, a high degree of fixation, acceptable migration and high water solubility with reasonable cost.The disazo dyes have the structure: ##STR1## Wherein: R is selected from ##STR2## Wherein the azo bonds are ortho to the --OH or NH.sub.2 groups;R.sub.1 is H, lower alkyl, lower alkoxy, or --CO.sub.2 M;R.sub.2 is H, lower alkyl, lower alkoxy, Cl;R.sub.3 is lower alkylene;R.sub.4 is H, --lower alkyl;R.sub.5 is H, lower alkyl, --CO.sub.2 M;R.sub.6 is OH or --NH.sub.2 ;R.sub.7 is H, --CH.sub.2 SO.sub.3 M;M is H, Na, Li, K, Mg, Ca, NH.sub.4 ; ##STR3## and n is 0, 1, 2.Type: GrantFiled: November 20, 1987Date of Patent: August 1, 1989Assignee: Crompton & Knowles CorporationInventor: James F. Feeman
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Patent number: 4843152Abstract: Complexes of the formula ##STR1## and salts thereof, whereineach of X.sub.1 and X.sub.2 is independently --NR.sub.1 R.sub.2,whereinR.sub.1 is hydrogen, C.sub.1-4 alkyl or C.sub.2-4 alkyl monosubstituted by hydroxy or C.sub.1-4 -alkoxy, andR.sub.2 is hydrogen; C.sub.1-10 alkyl; C.sub.2-8 hydroxyalkyl; C.sub.2-8 dihydroxyalkyl the hydroxy groups of which are attached to different carbon atoms; C.sub.1-6 alkyl monosubstituted by halo, cyano, --OR.sub.3, (C.sub.1-4 alkyl)carbonyl, (C.sub.1-4 -alkoxy)carbonyl, sulfo or sulfato; phenyl; phenyl substituted by 1 or 2 substituents selected from halo, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, acetamido and --SO.sub.2 --R.sub.4 ; phenyl(C.sub.1-4 alkyl); phenyl(C.sub.1-4 alkyl) the phenyl group of which is substituted by 1 or 2 substituents selected from halo, C.sub.1-4 -alkyl, C.sub.1-4 alkoxy, acetamido and --SO.sub.2 --R.sub.4 ; C.sub.5-6 cycloalkyl or C.sub.5-6 cycloalkyl substituted by 1 to 3 C.sub.1-4 alkyl groups,whereinR.sub.3 is C.sub.1-4 alkyl, C.sub.Type: GrantFiled: April 10, 1987Date of Patent: June 27, 1989Assignee: Sandoz Ltd.Inventors: Paul Doswald, Hans-Rudolf von Tobel
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Patent number: 4804747Abstract: (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: GrantFiled: October 16, 1986Date of Patent: February 14, 1989Assignee: Imperial Chemical Industries PLCInventors: Simon Allen, Paul F. Gordon, Richard A. Hann
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Patent number: 4764175Abstract: Metal-free compounds of the formula, ##STR1## and 1:1 copper complexes of metallizable metal-free compounds of said formula and internal and external salts of metal-free compounds of said formula and of 1:1 copper complexes of metallizable metal-free compounds of said formula, whereineach Q is independently linear or branched C.sub.2-6 alkylene; linear or branched C.sub.2-6 alkylene interrupted by --O--, --S-- or --NR.sub.4 --; linear or branched C.sub.3-6 alkylene monosubstituted or disubstituted by hydroxy or --*NHCO--CH.sub.2 --, wherein the * denotes the atom attached to the --NR.sub.4 -- radical,each R.sub.1 is independently hydrogen, halo, nitro, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, (C.sub.1-4 alkyl)carbonylamino, --SO.sub.2 NR.sub.3 R.sub.4, --CONR.sub.4 --C.sub.6 H.sub.5 or benzamido,R.sub.2 is hydrogen, hydroxy, halo, nitro, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, (C.sub.1-4 alkyl)carbonylamino or --NHCONR.sub.3 R.sub.4,X is --NR.sub.5 R.sub.6 or --N.sup..sym. R.sub.7 R.sub.8 R.sub.9 An.sup..crclbar.Type: GrantFiled: August 15, 1986Date of Patent: August 16, 1988Assignee: Sandoz Ltd.Inventors: Jacky Dore, Reinhard Pedrazzi
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Patent number: 4750936Abstract: Stabilized, aqueous dispersions of multivalent metal humates are disclosed as a compatible and functional component in printing ink formulations.Type: GrantFiled: January 27, 1987Date of Patent: June 14, 1988Assignee: Union Camp CorporationInventors: James C. West, William C. Firth, Jr.
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Patent number: 4668774Abstract: 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: GrantFiled: April 23, 1985Date of Patent: May 26, 1987Assignee: BASF AktiengesellschaftInventors: Hermann Loeffler, Rainer Dyllick-Brenzinger
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Patent number: 4663441Abstract: Compounds of the formula I ##STR1## where K.sup..sym. is a cation, R is methyl or is phenyl which is unsubstituted or substituted by chlorine, bromine, methyl, methoxy or ethoxy, R.sup.1 is hydrogen, chlorine, bromine or nitro, R.sup.2 is hydrogen, chlorine, bromine, nitro, sulfamyl or hydroxysulfonyl, X and Y are each --O-- or --COO--, Z is --O-- or --NH--, D is a radical of a diazo component of the aniline or naphthylamine series and K is a radical of a coupling component, are very useful for dyeing natural and synthetic polyamide textile fibers and leather.Type: GrantFiled: September 16, 1985Date of Patent: May 5, 1987Assignee: BASF AktiengesellschaftInventor: Klaus Grychtol
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Patent number: 4652632Abstract: Naphtholazo benzoylalkylene amines and salts thereof which are useful as dyes for acid-modified fibers, leather and paper, and which are represented by the formula ##STR1## wherein n is 0 or 1,A is an anion,R is C.sub.2 - to C.sub.4 -alkyleneR.sup.1 and R.sup.2 independently of one another are C.sub.1 - to C.sub.4 -alkyl, methoxyethyl, cyclohexyl, and R.sup.1 and R.sup.2 together are ##STR2## and R.sup.3 is methyl, ethyl or hydroxyethyl.Type: GrantFiled: April 1, 1985Date of Patent: March 24, 1987Assignee: BASF AktiengesellschaftInventor: Horst Colberg
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Patent number: 4649194Abstract: 1:2 Metal complexes of the formula ##STR1## wherein X.sub.1 is --O-- or ##STR2## and X.sub.2 is --O-- or ##STR3## the starred atom being attached A.sub.1 or A.sub.2, respectively, A.sub.1 is a diazo component radical of the benzene series,A.sub.2 is a diazo component radical of the benzene or naphthalene series,W is --CH.sub.3 or --COOH,R is hydrogen or --SO.sub.3 H,each of B.sub.1 and B.sub.2 is independently a coupling component radical or a phenolic hydroxy group-containing coupling component radical at least one phenolic hydroxy group of which is etherified or acylated,M is iron, cobalt or chromium, andn is 1 or 2,which complexes are useful as anionic dyestuffs having olive to brown colors for substrates such as natural and regenerated cellulose, natural and synthetic polyamides, polyurethane and anodized aluminum, especially leather.Type: GrantFiled: July 27, 1983Date of Patent: March 10, 1987Assignee: Sandoz Ltd.Inventor: Heinz Wicki
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Patent number: 4628082Abstract: Azobarbituric acid derivatives characterized in that in their free acid form they have the following tautomeric structure are disclosed: ##STR1## The azobarbituric acid derivatives are characterized in that X and Y rings can each carry one or two substituents from the series comprising .dbd.O, .dbd.S, .dbd.NR.sub.7, --NR.sub.6 R.sub.7, --OR.sub.6, --SR.sub.6, --COOR.sub.6, --CN, --CONR.sub.6 R.sub.7, --SO.sub.2 R.sub.8, ##STR2## alkyl, cycloalkyl, aryl and aralkyl, the total number of the endocyclic and exocyclic double bonds for each of the rings X and Y being three.The new azobarbituric acid derivatives are other than those of azobarbituric acid, azouracil and uracil-5-azobarbituric acid and their salts. The compounds are useful as pigments which pigments are useful for pigmented paints, in printing inks, distempers or emulsion paints, inter alia.Type: GrantFiled: May 14, 1985Date of Patent: December 9, 1986Assignee: Bayer AktiengesellschaftInventors: Manfred Lorenz, Karl H. Schundehutte
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Patent number: 4624907Abstract: An electrophotographic toner capable of being electrified negatively comprising:(a) a binder resin; and(b) a charge-controlling and coloring agent comprising at least one 2:1 type metal complex of the formula (I): ##STR1## where each of X.sub.1 and X.sub.2, which may be the same or different, is a hydrogen atom, a C.sub.1 -C.sub.5 alkyl group, a C.sub.1 -C.sub.5 alkoxy group, a nitro group or a halogen atom, each of m and m' is an integer of 1 to 3, each of R.sub.1 and R.sub.2, which may be the same or different, is a hydrogen atom, a C.sub.1 -C.sub.5 alkyl group, a C.sub.1 -C.sub.5 alkoxy group, a halgen atom, a nitro group, a sulfonamide group, a methylsulfonyl group, an ethylsulfonyl group, an acetyl amino group or a benzoyl amino group, each of n and n' is an integer of 1 to 3, Y.sup..sym. is an ammonium ion, an aliphatic ammonium ion, an alicyclic ammonium ion or a heterocyclic ammonium ion, and M is a chromium atom, a cobalt atom or an iron atom.Type: GrantFiled: November 8, 1984Date of Patent: November 25, 1986Assignee: Hodogaya Chemical Co., Ltd.Inventors: Isao Niimura, Katsuichi Motohashi, Hiroyoshi Yamaga, Noboru Akuzawa
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Patent number: 4618673Abstract: Asymmetric 1:2 chromium complexes of the formula, ##STR1## in which A is a group of the formula ##STR2## in which X is halogen, nitro or methyl,Y is hydrogen or nitro,* designates the carbon atom bound to the azo group,each Z is halogen or nitro, both substituents being the same,each of R.sub.1 and R.sub.2, independently, is phenyl or phenyl substituted by a total of up to three substituents selected from halogen, C.sub.1-6 alkyl, C.sub.1-6 alkoxy, nitro and cyano (maximum of two nitro and/or cyano), andM.sup..sym. is hydrogen or an equivalent of a non-chromophoric cation,with the proviso that the sulpho group is in salt form, and mixtures of two or more of such 1:2 asymmetric complexes, which complexes and mixtures are useful for dyeing nitrogen-containing organic substrates e.g., natural and synthetic polyamides such as wool, silk and nylon, polyurethanes and leather.Type: GrantFiled: September 22, 1981Date of Patent: October 21, 1986Assignee: Sandoz Ltd.Inventor: Jacky Dore
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Patent number: 4617382Abstract: The present invention relates to novel chromium complex dyes of the formula ##STR1## wherein Z is hydrogen, chloro, bromo, nitro, lower alkyl or acylamino;L is H.sub.Type: GrantFiled: April 13, 1983Date of Patent: October 14, 1986Assignee: Ciba-Geigy CorporationInventors: Gerhard Back, Fabio Beffa, Arthur Buhler
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Patent number: 4594410Abstract: Azo dyes of the formula ##STR1## and external salts thereof, wherein F is the residue of a monoazo or disazo compound in 1:1 metal complex form or of a trisazo, disazoazoxy or tetrakisazo compound in metal-free or 1:1 metal complex form,each X is independently --NR.sub.2 --Q--NR.sub.3 R.sub.4 or --NR.sub.2 --Q--N.sup..sym. R.sub.5 R.sub.6 R.sub.7,whereinQ is linear or branched C.sub.2-6 alkylene or --NH--CO--CH.sub.2 --,R.sub.2 is hydrogen or C.sub.1-4 alkyl,each of R.sub.3 and R.sub.4 is independently hydrogen; C.sub.1-6 alkyl; C.sub.2-6 alkyl monosubstituted by cyano or hydroxy in the 2-, 3-, 4-, 5- or 6-position; phenyl(C.sub.1-3 alkyl); phenyl(C.sub.1-3 alkyl) having, on the phenyl ring, 1, 2 or 3 substituents selected from chloro, C.sub.1-4 alkyl and C.sub.1-4 alkoxy; C.sub.5-6 cycloalkyl or C.sub.5-6 cycloalkyl substituted by 1, 2 or 3 C.sub.1-4 alkyl groups or --NR.sub.3 R.sub.Type: GrantFiled: August 18, 1982Date of Patent: June 10, 1986Assignee: Sandoz Ltd.Inventor: Reinhard Pedrazzi
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Patent number: 4581445Abstract: There are described novel cationic benzothiazole disazo compounds of the formula ##STR1## K independently of one another are each a coupling component, R independently of one another are each an unsubstituted or substituted C.sub.1 -C.sub.4 -alkyl group,R.sub.1 independently of one another are each hydrogen, unsubstituted or substituted C.sub.1 -C.sub.4 -alkyl, unsubstituted or substituted C.sub.1 -C.sub.4 -alkoxy, or halogen,X is the direct bond, --(CH.sub.2).sub.y wherein y is a number from 1 to 4, --CH.dbd.CH--, a phenylene group, a naphthylene group, a heterocyclic radical, an --NH-alkylene-(C.sub.1 -C.sub.6)--NH-- radical or an --NH-arylene-NH-- radical, andAn is an anion, with the proviso that when the coupling component K is a dimethylaminophenyl radical, the divalent bridge member X is not the --(CH.sub.2).sub.2 -- group are useful for dyeing and printing textile materials, leather and in particular paper. The dyeings obtained have good fastness properties, especially good fastness on paper to light.Type: GrantFiled: September 16, 1983Date of Patent: April 8, 1986Assignee: Ciba-Geigy CorporationInventor: Visvanathan Ramanathan
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Patent number: 4560747Abstract: A process for producing granulates of water-soluble dyes by means of fluidized bed granulation, wherein there is added a granulating auxiliary having a softening point or softening range between 30.degree. and 150.degree. C. and consisting of(a) at least one compound of the formula IA--(CH.sub.2 CH.sub.2 O).sub.n --H (I)in which A is the group R--O-- or ##STR1## wherein R is an aliphatic or alicyclic hydrocarbon radical having 8 to 22 carbon atoms, R' is an aliphatic hydrocarbon radical having 8 to 22 carbon atoms, and n is 10 to 200, preferably 20 to 150, or(b) a mixture of a compound of the formula II ##STR2## in which m is 50 to 500, and x is 3 to 5, with a compound of the formula IIIR.sub.1 --NH--CO--NH--R.sub.1 (III),in which each R.sub.1 independently of the other is hydrogen or methyl, or(c) a mixture of a compound of the formula I with at least one compound of the formula II or III.Type: GrantFiled: October 20, 1980Date of Patent: December 24, 1985Assignee: Ciba Geigy CorporationInventors: Beat Bruttel, Hansjorg Schneider, Werner H. Dorfel
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Patent number: 4483796Abstract: Disazo and polyazo compounds of the formula ##STR1## wherein each A is independently ##STR2## and each R.sub.3 is independently C.sub.1-4 alkyl, oreach A, R.sub.3 and the ##STR3## radical to which they are attached, taken together, independently, are ##STR4## wherein each R.sub.21 is independently halo, C.sub.1-4 alkyl or C.sub.1-4 alkoxy,p is 0, 1 or 2,the * denotes the carbon atom attached to the --N.dbd.N-- radical, andthe ** denotes the carbon atom attached to X,each R.sub.1 and the ##STR5## radical to which it is attached taken together, independently, are the radical of an aromatic or heterocyclic coupling component,each A.sub.1 and A.sub.2 taken together are --O--Me--O--, wherein Me is copper, cobalt, iron, nickel, manganese or zinc, oreach A.sub.1 is hydroxy, andeach A.sub.2 is independently hydrogen, hydroxy or C.sub.1-4 alkoxy,X is a direct bond or a bridging radical,each Y is independently a direct bond, C.sub.1-4 alkylene, --CO--NH--(CH.sub.2).sub.m --, --NH--CO--(CH.sub.2).sub.m -- or --SO.sub.Type: GrantFiled: August 18, 1982Date of Patent: November 20, 1984Assignee: Sandoz Ltd.Inventors: Paul Doswald, Emil Moriconi, Helmut Moser, Horst Schmid