Sulfonic Acid Group Bonded Directly To The Bicyclo Ring System (-(o=)s(=o) Oh, Wherein H Of The -oh May Be Replaced By The Ammonium Ion Or A Group Ia Or Iia Light Metal) Patents (Class 534/837)
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Patent number: 7446184Abstract: A compound of Formula (1) and salts thereof: wherein: Q is an optionally substituted aryl ring; Y is CO2H, SO3H or PO3H2; R and X are substituents; m is 0 to 3; n is 0 to 6; and q is 0 to 6. Also compositions comprising these compounds, ink-jet inks, an ink jet process and an ink-jet cartridge.Type: GrantFiled: December 6, 2004Date of Patent: November 4, 2008Assignee: Fujifilm Imaging Colorants LimitedInventors: Clive Edwin Foster, David Schofield, Julie Ann Downey, Neil Burnham, Philip John Double, Roy Bradbury
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Patent number: 6143062Abstract: Are disclosed disazo compounds represented by the general formula (1): ##STR1## wherein A represents a phenylene or naphthylene group which may be optionally substituted; each of R.sup.1 and R.sup.2 represent independently a hydrogen atom, an alkyl group or a phenyl group which may be optionally substituted; and m is 1 or 2. The compounds are highly water-soluble and are stable to long term storage. Ink compositions comprising the compounds of the invention can produce a printed image with full depth of shade and are excellent in resistance to water.Type: GrantFiled: December 21, 1998Date of Patent: November 7, 2000Assignee: Nippon Kayaku Kabushiki KaishaInventors: Takashi Miyazawa, Toru Tabei, Isao Yamaguchi, Yasuo Shirasaki, Junko Yoshioka
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Patent number: 5989326Abstract: Disazo dyes formula (VIII) ##STR1## or of formula (IX) ##STR2## Where A, R.sub.1, R.sub.2, n and M are as defined in the specification are excellent dyes for ink jet printing.Type: GrantFiled: February 3, 1998Date of Patent: November 23, 1999Assignee: Ilford Imaging Switzerland GmbHInventor: Heinz Peter
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Patent number: 5882392Abstract: A dye of Formula (1) and salts thereof: ##STR1## in which R is H, --NHC.sub.1-4 -alkylN(C.sub.1-4 -alkyl).sub.2 or ##STR2## R.sub.1 and R.sub.2 each independently is H, optionally substituted C.sub.1-4 -alkyl or optionally substituted aryl;R.sub.3 is C.sub.1-4 -alkyl;R.sub.4 is C.sub.1-4 -alkyl or OC.sub.1-4 -alkyl;R.sub.5 is H;R.sub.6 is COOH; andn is 1, 2 or 3.The dyes are useful for preparing ink jet printer inks.Type: GrantFiled: October 9, 1997Date of Patent: March 16, 1999Assignee: Zeneca LimitedInventors: Peter Gregory, Prahalad Manibhai Mistry, Roy Bradbury, Paul Wight
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Patent number: 5663309Abstract: Azo dyes of the formula ##STR1## in which R.sub.1 is hydrogen or substituted or unsubstituted phenylamino,R.sub.2 is hydrogen, amino or N-mono- or N,N-di-C.sub.1 -C.sub.4 alkylamino,R.sub.3 is hydrogen or hydroxyl,R.sub.4 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.2 -C.sub.4 alkanoylamino, ureido or halogen andK is as defined in claim 1,the azo dyes of the formula (1) comprising at least one and not more than two sulfo groups,are particularly suitable for dyeing or printing cellulosic fibre materials or naturally occurring or synthetic polyamide fibre materials with a high dyeing yield, and give dyeings and prints with good fastness properties.Type: GrantFiled: December 5, 1995Date of Patent: September 2, 1997Assignee: Ciba-Geigy CorporationInventor: Rudolf Hurter
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Patent number: 5647897Abstract: An ink composition for ink jet recording is provided which can satisfy property requirements of quality of print, drying property of print, clogging resistance, water resistance, storage stability, and nonattacking on members constituting an ink passage, such as a printing head. The ink composition for ink jet recording comprises a dye represented by the following formula (I), glycerin, pyrrolidone, a monohydric lower alcohol, a tri(hydroxyalkyl)amine, and water: ##STR1## wherein R.sup.1 represents phenyl or naphthyl substituted by a group selected from hydroxyl, --NH.sub.2, --SO.sub.3 M and --COOM, R.sup.2 represents carboxyalkyl, alkoxyalkyl, phenyl, or alkanoyl, R.sup.3, R.sup.4, and R.sup.5 represent hydrogen or --SO.sub.3 M.Type: GrantFiled: October 31, 1995Date of Patent: July 15, 1997Assignee: Seiko Epson CorporationInventors: Yasuhiro Ouki, Miharu Kanaya, Hiroko Hayashi, Kiyohiko Takemoto, Masaaki Itano
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Patent number: 5510468Abstract: There are described benzophenoneazo dyes of the formula ##STR1## where the ring A can be benzofused and a benzofused ring A can be overbridges,m is 1 or 2,K is the radical of a coupling component,Y is hydrogen or arylazo,one of the two radicals X.sup.1 and X.sup.2 is hydrogen and the other is hydroxysulfonyl,R.sup.1, R.sup.2 and R.sup.3 are independently of the others hydrogen, halogen, C.sub.1 -C.sub.12 -alkyl, cyclohexyl, phenyl, 2-hydroxy-ethylsulfonyl or C.sub.1 -C.sub.4 -alkoxy or, when m is 1 and Y is hydrogen, one of these substituents can also be the radical of the formula ##STR2## where L.sup.1 is a chemical bond or a bridge member, and X.sup.1, X.sup.2, R.sup.4, K and the ring A are each as defined above, andR.sup.4 is hydrogen, halogen or C.sub.1 -C.sub.Type: GrantFiled: July 27, 1994Date of Patent: April 23, 1996Assignee: BASF AktiengesellschaftInventors: Gunther Lamm, Helmut Reichelt, Ortwin Schaffer
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Patent number: 5380859Abstract: There are described benzophenoneazo dyes of the formula ##STR1## where the ring A can be benzofused and a benzofused ring A can be overbridged,m is 1 or 2,K is the radical of a coupling component,Y is hydrogen or arylazo,one of the two radicals X.sup.1 and X.sup.2 is hydrogen and the other is hydroxysulfonyl,R.sup.1, R.sup.2 and R.sup.3 are independently of the others hydrogen, halogen, C.sub.1 -C.sub.12 -alkyl, cyclohexyl, phenyl, 2-hydroxyethylsulfonyl or C.sub.1 -C.sub.4 -alkoxy or, when m is 1 and Y is hydrogen, one of these substituents can also be the radical of the formula ##STR2## where L.sup.1 is a chemical bond or a bridge member, andX.sup.1, X.sup.2, R.sup.4, K and the ring A are each as defined above, andR.sup.4 is hydrogen, halogen or C.sub.1 -C.sub.Type: GrantFiled: July 16, 1993Date of Patent: January 10, 1995Assignee: Basf AktiengesellschaftInventors: Gunther Lamm, Helmut Beichelt, Ortwin Schaffer
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Patent number: 5366543Abstract: The present invention provides a disazo salt-forming dye having excellent solubility with organic solvents, especially alcohols and glycols.The present invention thus provides a disazo salt-forming dye represented by the Formula (I): ##STR1## or the Formula (II): ##STR2## wherein Ka.sup.+ represents a cation of an amine which is substituted with at least one linear or cyclic alkyl group or aralkyl group having 6-12 carbon atoms which may be branched or interrupted by oxygen.Type: GrantFiled: June 9, 1993Date of Patent: November 22, 1994Assignee: Orient Chemical Industries, Ltd.Inventors: Takashi Ono, Tatsuya Yagyu, Tetsui Akase
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Patent number: 5332806Abstract: Azo dyes of the formula ##STR1## where A and B are each independently of the other substituted or unsubstituted phenyl or naphthyl and X is --N(R.sub.1)--SO.sub.2 --, --O--SO.sub.2 -- or --SO.sub.2 --N(R.sub.1)--, where R.sub.1 is hydrogen or C.sub.1 -C.sub.8 alkyl, produce very fast dyeings on nitrogen-containing or hydroxyl-containing fibre materials, paper or leather.Type: GrantFiled: December 10, 1992Date of Patent: July 26, 1994Assignee: Ciba-Geigy CorporationInventor: Rudolf Hurter
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Patent number: 5258505Abstract: Disclosed herein is an azo compound represented by the formula ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 each are a group or atom selected from the group consisting of a hydrogen atom, alkyl groups having 1 to 4 carbon atoms, a methoxy group, halogen atoms, COOM and COOR.sub.4 in which R.sub.4 is an alkyl group having 1 to 4 carbon atoms, and M denotes an alkali metal atom, or an ammonium or organic ammonium ion. An ink containing this compound is suitable for use in an ink-jet recording.Type: GrantFiled: March 27, 1992Date of Patent: November 2, 1993Assignee: Canon Kabushiki KaishaInventors: Tsuyoshi Eida, Mayumi Yamamoto, Takao Yamamoto
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Patent number: 5203912Abstract: A dye which, in the free acid form, has the formula ##STR1## wherein W is COOHX is selected from H, COOH, SO.sub.3 H, halo, hydroxy, nitro, cyano, C.sub.1-6 -alkyl, C.sub.1-6 -alkoxy and C.sub.1-6 -acylamino;Y is H, COOH or SO.sub.3 H;Z is H, COOH or SO.sub.3 H;R & R.sup.1 are each independently H or C.sub.1-6 -alkyl substituted by 0, 1 or 2 --COOR.sup.2 groups; andR.sup.2 is H or C.sub.1-6 -alkyl;provided that there are at least two COOH groups and that the number of COOH groups is equal to or greater than the number of SO.sub.3 H groups.The dye is adapted for the preparation of inks for use in ink jet printing in which it displays high water-fastness on paper.Type: GrantFiled: June 24, 1991Date of Patent: April 20, 1993Assignee: Imperial Chemical Industries PLCInventors: David Greenwood, Nigel Hughes, Ronald W. Kenyon, Suraj L. Hindagolla
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Patent number: 5198022Abstract: A alkali-soluble dye for a waterfast ink having structural formula as follows: ##STR1## and an ink containing the dye dissolved in water. Printing from the ink is insoluble below pH 6.0; is an intense black at low concentration; and remains black on acid papers. The aqueous inks are stable and exhibit good printhead nozzle maintenance.Type: GrantFiled: January 17, 1992Date of Patent: March 30, 1993Assignee: Lexmark International, Inc.Inventors: Rodney O. Aulick, Bradley L. Beach, Donald L. Elbert, Terence E. Franey, James F. Feeman, John M. Olson, Allen C. Sanders, Robert L. Vollmer
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Patent number: 5175260Abstract: Disazo dyes suitable for preparing inks have the formula ##STR1## where m is 1 or 2,n is 0 or 1,Z.sup.1 is hydrogen or substituted or unsubstituted C.sub.1 -C.sub.4 -alkyl,Z.sup.2 is hydrogen, substituted or unsubstituted C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkanoyl, substituted or unsubstituted benzoyl, C.sub.1 -C.sub.4 -alkylsulfonyl, substituted or unsubstituted phenylsulfonyl or a derivatized 1,3,5-triazinyl radical, andD is the radical of a diazo component of the class of the thiazole, thiophene, aminobenzoic acid or phenylenediamine compounds.Type: GrantFiled: August 8, 1991Date of Patent: December 29, 1992Assignee: BASF AktiengesellschaftInventors: Gunter-Rudolf Schroeder, Udo Mayer
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Patent number: 5062893Abstract: Inks are provided comprising (a) at least two dyes corresponding to the formula ##STR1## wherein W is COOH,X is H, or COOH,Y is H, COOH, or SO.sub.3 H,Z is H, COOH, or SO.sub.3 H, andR is H, CH.sub.2 COOH, or CH.sub.2 CH.sub.2 COOH;with the proviso that there are at least two COOH groups and that the number of COOH groups is equal to or greater than the number of SO.sub.3 H groups, and (b) a solvent which may be water or a mixture of water and a water-soluble organic solvent provide excellent waterfast prints on paper. The inks preferably have a pH from about 7 to about 9.5. Also preferably, a phosphate is added to reduce kogation and a metal chelating agent is added to further reduce nozzle clogging.Type: GrantFiled: June 22, 1990Date of Patent: November 5, 1991Assignee: Hewlett-Packard CompanyInventors: Raymond J. Adamic, Palitha Wickramanayake, Suraj L. Hindagolla, Garold E. Radke, David J. Halko
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Patent number: 4963189Abstract: Inks are provided comprising (a) a dye corresponding to the formula ##STR1## wherein W is COOH,X is H, or COOH,Y is H, COOH, or SO.sub.3 H,Z is H, COOH, or SO.sub.3 H, andR is H, CH.sub.2 COOH, or CH.sub.2 CH.sub.2 COOH;with the proviso that there are at least two COOH groups and that the number of COOH groups is equal to or greater than the number of SO.sub.3 groups, and (b) a solvent which may be water or a mixture of water and a water-soluble organic solvent provide excellent waterfast prints on paper. The inks preferably have a pH from about 7 to about 9.5.Type: GrantFiled: August 24, 1989Date of Patent: October 16, 1990Assignee: Hewlett-Packard CompanyInventor: Suraj L. Hindagolla
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Patent number: 4841037Abstract: A naphthalene trisazo compound represented by the general formula (I) or (II): ##STR1## wherein A and B each represents a substituted or unsubstituted benzene or naphthalene ring; m represents zero or 1; and M represents an alkali metal atom, ammonium or H.Am (wherein Am represents an amine); or ##STR2## wherein X represents a hydrogen atom, a lower alkyl group, a phenyl group or a phenyl group substituted by --SO.sub.3 M; m represents zero or 1; M represents an alkali metal atom, ammonium or H.Am (wherein Am represents an amine); A, B and C each represents a substituted or an unsubstituted benzene or naphthalene ring, provided that B and C do not represent a naphthalene ring at the same time. A recording liquid containing these compounds is suitable for use in an ink-jet recording system.Type: GrantFiled: June 10, 1986Date of Patent: June 20, 1989Assignees: Canon Kabushiki Kaisha, Mitsubishi Chemical Industries LimitedInventors: Tokuya Ohta, Masatsune Kobayashi, Yuko Suga, Konoe Miura, Hiroshi Takimoto, Tomio Yoneyama
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Patent number: 4772687Abstract: Metal complex dyestuffs which in the form of the free acid correspond to the formula ##STR1## in which the substituents have the meaning given in the description are, depending on the meanings of the substituents, suitable for use as reactive dyestuffs for cotton, wool or polyamide, as direct dyestuffs for cotton or as pigment dyestuffs. Dyeings are obtained which have good fastness properties, in particular good wet-, light- and chlorine fastness.Type: GrantFiled: May 1, 1986Date of Patent: September 20, 1988Assignee: Bayer AktiengesellschaftInventor: Hermann Henk
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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: 4544739Abstract: Chromium complex dyes which, in the form of the free acid, have the formula ##STR1## wherein Z is hydrogen, nitro, chlorine or naphthylazo or phenylazo, wherein naphthyl or phenyl is unsubstituted or substituted by nitro, chlorine, bromine, C.sub.1-5 -alkyl or C.sub.1-5 -alkoxy, A is naphthyl or phenyl containing the oxygen atom in o-position to the azomethine and wherein naphthyl or phenyl is unsubstituted or substituted by C.sub.1-5 -alkyl, halogen or naphthylazo or phenylazo wherein naphthyl or phenyl is unsubstituted or substituted by nitro, chlorine, bromine, C.sub.1-5 -alkyl or C.sub.1-5 -alkoxy, D is sulfophenyl which is unsubstituted or substituted by nitro or chlorine, or sulfonaphthyl which is unsubstituted or substituted by nitro, and is bonded to the azo group in the ortho-position to the oxygen atom and R is chloroacetyl, bromoacetyl, .alpha.-chloroacryloyl, .alpha.-bromoacryloyl, .alpha.,.beta.-dichloropropionyl, .alpha.,.beta.Type: GrantFiled: September 28, 1982Date of Patent: October 1, 1985Assignee: Ciba-Geigy CorporationInventors: Hans U. Schutz, Arthur Buhler