Additional Hydroxy Or Nitrogen, Other Than As Nitro, Nitroso Or Azo, Bonded Directly To The Bicyclo Ring System Patents (Class 534/836)
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Publication number: 20150141629Abstract: The present invention relates to a water-resistant organic thin film obtained by crosslinking, with organic nitrogen compounds, an organic thin film comprising an organic dye having an anionic group, wherein the organic nitrogen compounds are first, second, and third acyclic organic nitrogen compounds each having two or more nitrogen atoms per molecule, wherein the nitrogen atoms of each of the first, second, and third organic nitrogen compounds are each in a cationic group, and the relation A?0.4 nm<B<C is satisfied, wherein A represents a distance (nm) between adjacent nitrogen atoms in the first organic nitrogen compound, B represents a distance (nm) between adjacent nitrogen atoms in the second organic nitrogen compound, and C represents a distance (nm) between adjacent nitrogen atoms in the third organic nitrogen compound.Type: ApplicationFiled: June 10, 2013Publication date: May 21, 2015Applicant: NITTO DENKO CORPORATIONInventors: Hiroshi Tomohisa, Toru Umemoto, Shoichi Matsuda, Tadayuki Kameyama
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Publication number: 20150126717Abstract: This invention relates to bis-azo colorants for use as bluing agents, laundry care compositions comprising bis-azo colorants that may serve as bluing agents, processes for making such bluing agents and laundry care compositions and methods of using the same. The bluing agents are generally comprised of at least two components: at least one chromophore component and at least one polymeric component. These bluing agents are advantageous in providing a whitening effect to fabrics, while not building up over time and causing undesirable blue discoloration to the treated fabrics.Type: ApplicationFiled: January 8, 2015Publication date: May 7, 2015Inventors: Robert L. Mahaffey, JR., Xiaoyong Michael Hong, Eduardo Torres, Dominick J. Valenti, Gregory Scot Miracle
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Patent number: 8962815Abstract: This invention relates to bis-azo colorants for use as bluing agents, laundry care compositions comprising bis-azo colorants that may serve as bluing agents, processes for making such bluing agents and laundry care compositions and methods of using the same. The bluing agents are generally comprised of at least two components: at least one chromophore component and at least one polymeric component. These bluing agents are advantageous in providing a whitening effect to fabrics, while not building up over time and causing undesirable blue discoloration to the treated fabrics.Type: GrantFiled: January 24, 2013Date of Patent: February 24, 2015Assignee: Milliken & CompanyInventors: Robert L Mahaffey, Jr., Xiaoyong Michael Hong, Eduardo Torres, Dominick J Valenti, Gregory Scot Miracle
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Patent number: 8785607Abstract: The present invention relates to a method for manufacturing a water resistant optically anisotropic film comprising: a water resistant treatment step of bringing an optically anisotropic film containing an organic dye having an anionic group into contact with a water resistant treatment liquid containing a multivalent metal salt or a compound having two or more nitrogen atoms in a molecule thereof; and a cleaning step of cleaning the optically anisotropic film after the water resistant treatment, using a cleaning liquid containing a hydrophilic organic compound.Type: GrantFiled: August 12, 2011Date of Patent: July 22, 2014Assignee: Nitto Denko CorporationInventors: Toru Umemoto, Tadayuki Kameyama
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Publication number: 20130227797Abstract: The invention relates to the dyeing of human keratinous fibres, in particular the hair, using anionic direct dyes or acid dyes having a tetraalkylammonium counterion of formula (I) with Col(?)m. R1, R2, R3, R4, m, and n as defined in the description. A subject-matter of the invention is a dyeing composition comprising an anionic dye of formula (I) and a method for dyeing keratinous fibres, such as the hair, employing the said composition. A subject-matter of the invention is likewise novel dyes of formula (I) and their uses for the colouring of keratinous fibres. This composition makes it possible to obtain a chromatic, powerful and particularly persistent colouring on keratinous fibres.Type: ApplicationFiled: November 16, 2011Publication date: September 5, 2013Applicant: L'OREALInventor: Andrew Greaves
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Publication number: 20130211058Abstract: This invention relates to bis-azo colorants for use as bluing agents, laundry care compositions comprising bis-azo colorants that may serve as bluing agents, processes for making such bluing agents and laundry care compositions and methods of using the same. The bluing agents are generally comprised of at least two components: at least one chromophore component and at least one polymeric component. These bluing agents are advantageous in providing a whitening effect to fabrics, while not building up over time and causing undesirable blue discoloration to the treated fabrics.Type: ApplicationFiled: January 24, 2013Publication date: August 15, 2013Applicant: MILLIKEN & COMPANYInventor: Milliken & Company
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Patent number: 8477268Abstract: Azo compounds represented by formula (1) (In the formula, R1 represents a lower alkoxy group with a sulfone group. R2-R5 each independently represents a hydrogen atom, lower alkyl group or lower alkoxy group. X is an optionally substituted amino group, optionally substituted benzoylamino group, optionally substituted phenylamino group, optionally substituted phenyl azo group or optionally substituted naphthotriazole group. m represents 1 or 2 and n represents 0 or 1.) and salts thereof.Type: GrantFiled: May 19, 2009Date of Patent: July 2, 2013Assignees: Nippon Kayaku Kabushiki Kaisha, Polatechno Co., Ltd.Inventors: Takuto Nishiguchi, Hiroaki Ohno, Takahiro Higeta, Yuichi Sadamitsu
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Publication number: 20120101265Abstract: This invention relates to bis-azo colorants for use as bluing agents, laundry care compositions comprising bis-azo colorants that may serve as bluing agents, processes for making such bluing agents and laundry care compositions and methods of using the same. The bluing agents are generally comprised of at least two components: at least one chromophore component and at least one polymeric component. These bluing agents are advantageous in providing a whitening effect to fabrics, while not building up over time and causing undesirable blue discoloration to the treated fabrics.Type: ApplicationFiled: October 22, 2010Publication date: April 26, 2012Inventors: Robert L. Mahaffey, JR., Xiaoyong Michael Hong, Eduardo Torres, Dominick J. Valenti, Gregory S. Miracle
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Publication number: 20120059157Abstract: The present invention relates to a method for manufacturing a water resistant optically anisotropic film comprising: a water resistant treatment step of bringing an optically anisotropic film containing an organic dye having an anionic group into contact with a water resistant treatment liquid containing a multivalent metal salt or a compound having two or more nitrogen atoms in a molecule thereof; and a cleaning step of cleaning the optically anisotropic film after the water resistant treatment, using a cleaning liquid containing a hydrophilic organic compound.Type: ApplicationFiled: August 12, 2011Publication date: March 8, 2012Applicant: NITTO DENKO CORPORATIONInventors: Toru Umemoto, Tadayuki Kameyama
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Publication number: 20110164208Abstract: Azo compounds represented by formula (1) (In the formula, R1 represents a lower alkoxy group with a sulfone group. R2-R5 each independently represents a hydrogen atom, lower alkyl group or lower alkoxy group. X is an optionally substituted amino group, optionally substituted benzoylamino group, optionally substituted phenylamino group, optionally substituted phenyl azo group or optionally substituted naphthotriazole group. m represents 1 or 2 and n represents 0 or 1.) and salts thereof.Type: ApplicationFiled: May 19, 2009Publication date: July 7, 2011Applicants: NIPPON KAYAKU KABUSHIKI KAISHA, POLATECHNO CO., LTD.Inventors: Takuto Nishiguchi, Hiroaki Ohno, Takahiro Higeta, Yuichi Sadamitsu
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Publication number: 20100257678Abstract: Disclosed is an azo compound represented by the formula (1) below, a salt thereof, or a copper complex salt compound thereof. (In the formula, R1 and R2 independently represent a hydrogen atom, a sulfonic acid group, a lower alkyl group or a lower alkoxyl group; R3-R6 independently represent a hydrogen atom, a lower alkyl group or a lower alkoxyl group; R7 represents a lower alkyl group or a lower alkoxyl group; and n represents 0 or 1.Type: ApplicationFiled: June 21, 2007Publication date: October 14, 2010Inventors: Yuichi Sadamitsu, Takahiro Higeta
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Publication number: 20100233443Abstract: Compounds of the general formula (I) a process for their preparation and their use for dyeing and/or printing organic substrates.Type: ApplicationFiled: June 21, 2007Publication date: September 16, 2010Applicant: CLARIANT FINANCE (BVI) LIMITEDInventor: Rainer Nusser
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Patent number: 7638611Abstract: A polarizer of the present invention comprises an azo compound which is represented by the following general formula (I). In the general formula (I), Q1 represents an optionally substituted aryl group, Q2 represents an optionally substituted arylene group, M represents a counter ion, l represents an integer of from 1 to 6, and m represents an integer of from 0 to 5 (l+m?6).Type: GrantFiled: January 9, 2009Date of Patent: December 29, 2009Assignee: Nitto Denko CorporationInventors: Shoichi Matsuda, Kyoko Nishiguchi, Tadayuki Kameyama
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Publication number: 20090083913Abstract: The invention relates to novel dyes of the formula (1) in which D represents a phenyl or naphthalene residue which is substituted by one or two sulphonic Acid or carboxylic acid groups and, optionally, by one or two groups selected from C1-C4alkyl, hydroxyl and nitro, each R1 and R2, independently, represent hydrogen or, a C1-C4alkyl group, R?1 represents hydrogen, hydroxyl, C1-C4alkyl or C1-C4hydroxyalkyl, R3 represents hydrogen, C1-C4alkyl or phenyl, which is unsubstituted or substituted by one or two groups selected from C1-C4alkyl, C1-C4alkoxy, halogen, hydroxyl, —NH2, nitro, —SO3M and —CO2M and M represents hydrogen, an alkaline or alkaline earth metal, ammonium or ammonium that is mono-, di-, tri- or tetrasubstituted by C1-C4alkyl or C2-C4hydroxyalkyl or a polyglycolammonium cation and also known dyes of formula (5), in which D? represents a phenyl or naphthalene residue which is substituted by one or two sulphonic acid or carboxylic acid groups and, optionally, by one or two groups selected from C1-C4aType: ApplicationFiled: June 26, 2006Publication date: April 2, 2009Inventors: Adolf Kaser, Wolfgang Schlenker
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Patent number: 6712893Abstract: A compound of Formula (1) and salts thereof: In the formula, m is 1, 2 or 3; X is H or SO3H; R1 and R2 are each independently selected from optionally substituted alkyl and optionally substituted alkoxy; and R4 and R5 are each independently H, optionally substituted alkyl or optionally substituted aryl. When (i) at least one of R1 and R2 carries an —OH group; and (ii) when X is H at least one of R1 and R2 is optionally substituted alkyl. The compounds are useful as dyes for ink jet printing inks.Type: GrantFiled: June 28, 2001Date of Patent: March 30, 2004Assignee: Avecia LimitedInventors: Prahalad Manibhai Mistry, Roy Bradbury
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Patent number: 6695899Abstract: A compound of Formula (1) and salts thereof: wherein: A is a substituted phenyl group carrying a group of the formula —NR3R4 and an ortho carboxy group; n is 0 or 1; L1 and L2 are each independently H, optionally substituted alkyl, optionally substituted cycloalkyl or optionally substituted aryl, or L1 and L2 together with the N atom to which they are attached form an optionally substituted 5- or 6-membered ring; R1 and R2 are each independently optionally substituted alkyl or optionally substituted alkoxy; and R3 and R4 are each independently H, optionally substituted alkyl, optionally substituted cycloalkyl or optionally substituted aryl, or R3 and R4 together with the N atom to which they are attached form an optionally substituted 5- or 6-membered ring; or R3 is H, optionally substituted alkyl, optionally substituted cycloalkyl or optionally substituted aryl; and R4 is an acyl group.Type: GrantFiled: March 26, 2002Date of Patent: February 24, 2004Assignee: Avecia LimitedInventor: Prahalad Manibhai Mistry
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Patent number: 6689201Abstract: A compound of Formula (1) and salts thereof are useful as dyes for ink jet printing inks. In the formula (1), A is optionally substituted phenyl (other than carboxyl substituted); R1 and R2 are each independently optionally substituted alkyl or optionally substituted alkoxy; and R4 and R5 are each independently H, alkyl or optionally substituted aryl. In formula (1) at least one of R1 and R2 carries an —OH group.Type: GrantFiled: June 28, 2001Date of Patent: February 10, 2004Assignee: Avecia LimitedInventors: Prahalad Manibhai Mistry, Roy Bradbury
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Patent number: 6559292Abstract: Compounds of Formula (1) and salts thereof: wherein: A is optionally substituted phenyl; R1 and R2 are each independently optionally substituted alkyl or optionally substituted alkoxy; and R4 and R5 are each independently H, optionally substituted alkyl or optionally substituted aryl; provided that (i) at least one of R1 and R2 carries an —OH group; and (ii) A is not of the formula: wherein m is 1, 2 or 3. The compounds are useful as dyes for ink jet printing inks.Type: GrantFiled: June 28, 2001Date of Patent: May 6, 2003Assignee: Avecia LimitedInventors: Prahalad Manibhai Mistry, Roy Bradbury
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Patent number: 6451989Abstract: Provided are novel black azo dyes which are useful in ink compositions, especially ink jet ink compositions. The dyes and ink compositions of the present invention exhibit a good balance of optical density, print reliability, water fastness and light fastness.Type: GrantFiled: June 18, 2001Date of Patent: September 17, 2002Assignee: Lexmark International, Inc.Inventors: Bradley Leonard Beach, Ann P Holloway, James F Feeman
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Patent number: 6288217Abstract: Provided are novel black azo dyes which are useful in ink compositions, especially ink jet ink compositions. The dyes and ink compositions of the present invention exhibit a good balance of optical density, print reliability, water fastness and light fastness.Type: GrantFiled: August 18, 2000Date of Patent: September 11, 2001Assignee: Lexmark International, Inc.Inventors: Bradley Leonard Beach, Ann P Holloway, James F Feeman
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Patent number: 6084078Abstract: The novel disazo dyestuffs of the formula (I) in which the substituents and indices have the meanings given in the description, are outstandingly suitable for dyeing cellulosic materials in red-violet to blue brilliant color shades.Type: GrantFiled: December 17, 1997Date of Patent: July 4, 2000Assignee: Bayer AktiengesellschaftInventor: Winfried Mennicke
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Patent number: 5969115Abstract: Bisazo dyes of formula (IX) ##STR1## and of formula (X) ##STR2## wherein A, R.sub.4, M and n are as defined in the specification, are excellent dyes for dyeing and printing of cellulose containing materials and especially for the preparation of inks for ink jet printing.Type: GrantFiled: October 1, 1998Date of Patent: October 19, 1999Assignee: Ilford Imaging Switzerland GMBHInventor: Heinz Peter
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Patent number: 5891230Abstract: A bisazo dye of Formula (1) and salts thereof: ##STR1## in which R is H;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 and R.sub.4 are each independently --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 ink jet printing.Type: GrantFiled: October 9, 1997Date of Patent: April 6, 1999Assignee: Zeneca LimitedInventors: Peter Gregory, Prahalad Manibhai Mistry, Roy Bradbury, Paul Wight
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Patent number: 5888286Abstract: A bisazo dye of Formula (1) and salts thereof: ##STR1## wherein: 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 --NH.sub.2 ;R.sub.4 is OC.sub.1-4 -alkyl;each R.sub.5 independently is --COOH or --SO.sub.3 H; andn is 1,2, or 3.Also claimed are inks containing the dye, a process of ink jet printing using the inks and substrates coloured by the inks.Type: GrantFiled: October 9, 1997Date of Patent: March 30, 1999Assignee: Zeneca LimitedInventors: Peter Gregory, Prahalad Manibhai Mistry, Roy Bradbury, Paul Wight
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Patent number: 5795970Abstract: A disazo dye composition comprising at least a disazo dye represented by the formula (I) and a disazo dye represented by the formula (II): ##STR1## (wherein X and Y indicate an alkoxy group having 1 to 4 carbon atoms, and M indicates hydrogen or a cation selected from the group consisting of, alkaline metal, NH.sub.4, alkyl-substituted ammonium, alkanolammonium, morpholinium and piperidinium), wherein, when the disazo dye composition is analyzed by liquid chromatography, the area ratio of the peak area (Sp) of the disazo dye represented by the formula (I) to the peak area (Sc) of the disazo dye represented by the formula (II), that is Sp:Sc is from 1:0.4 to 1:2.4. This disazo dye composition provides a high quality image, rapid ink fixing and the like even on the plain paper.Type: GrantFiled: August 22, 1996Date of Patent: August 18, 1998Assignees: Orient Chemical Industries, Ltd., Seiko Epson CorporationInventors: Takashi Ono, Tatsuya Yagyu, Yoshihiro Sawatari, Masaki Sasaki, Miharu Kanaya, Hiroko Hayashi, Akio Owatari, Yasuhiro Ouki
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Patent number: 5744591Abstract: A dyestuff of the general formula (1), ##STR1## wherein R.sub.1 is H or C.sub.1 -C.sub.4 alkyl; R.sub.2 is a phenyl or naphthyl group, which is unsubstituted or substituted by --Cl, --Br, --I, --CH.sub.3, --C.sub.2 H.sub.5, --C.sub.3 H.sub.7, --C.sub.4 H.sub.9, --OH, --OCH.sub.3, --OC.sub.2 H.sub.5, --NO.sub.2, --NHCOCH.sub.3 or --COOH. The dyestuff of the present invention is suitable for dyeing and printing of materials containing hydroxyl group or amide group, in particular animal fibrous material, synthetic polyamide and polyurethane fibers.Type: GrantFiled: May 27, 1997Date of Patent: April 28, 1998Assignee: Everlight USA, Inc.Inventor: Min-Mey Yei
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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: 5281263Abstract: According to the present invention there is provided a compound which, in the free acid form, is of the Formula (1): ##STR1## wherein A is an optionally substituted phenyl or naphthyl group;Z is H, CO.sub.2 H, SO.sub.3 H or SO.sub.2 NH.sub.2 ;T is H or SO.sub.3 H;R.sup.1 is H or optionally substituted alkyl;V is H, CO.sub.2 H, SO.sub.3 H, CH.sub.3 or Cl; provided that the compound of Formula (1) has at least as many CO.sub.2 H groups as SO.sub.3 H groups.The compound is useful as a colorant for inks used in ink jet printing.Type: GrantFiled: January 21, 1992Date of Patent: January 25, 1994Assignee: Imperial Chemical Industries PLCInventors: Peter Gregory, Prahalad M. Mistry
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Patent number: 5250107Abstract: A water-fast ink composition and method for making the same. A selected chemical dye having at least one functional group with an extractable hydrogen atom thereon (e.g. --COOH, --NH.sub.2, or --OH) is combined with an ammonium zirconium polymer salt (e.g. ammonium zirconium carbonate, ammonium zirconium acetate, ammonium zirconium sulfate, ammonium zirconium phosphate, and ammonium zirconium oxalate). The resulting mixture preferably contains about 0.01-5.0% by weight ammonium zirconium polymer salt and about 0.5-5.0% by weight chemical dye. Upon dehydration of the mixture, the ammonium zirconium polymer salt and chemical dye form a cross-linked dye complex which is stable and water-fast. The mixture may be dispensed onto a variety of substrates (e.g. paper) using thermal inkjet or other printing systems.Type: GrantFiled: July 31, 1991Date of Patent: October 5, 1993Assignee: Hewlett-Packard CompanyInventor: Steven J. Bares
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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: 5149366Abstract: A disazo compound of the formula (I) in the free acid form, ##STR1## and an ink jet recording ink composition containing the same are provided, and the composition is superior in stability during storage or use, heat resistance, image clearness, water resistance and light fastness, and has a desirable tint as a red color.Type: GrantFiled: October 9, 1991Date of Patent: September 22, 1992Assignees: Sumitomo Chemical Company, Limited, Taoka Chemical CompanyInventors: Hideo Kawashita, Mituhiro Ohta, Kazuya Ogino
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Patent number: 5118737Abstract: 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;M is H, ammonium, or a monovalent metal;X (i) NR.sup.1 R.sup.2, (ii) NR.sup.3 R.sup.4, in which R.sup.3 and R.sup.Type: GrantFiled: June 22, 1990Date of Patent: June 2, 1992Assignee: Canon Kabushiki KaishaInventors: Anthony G. W. Baxter, Stephen B. Bostock, David Greenwood
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Patent number: 5075428Abstract: A dyestuff of the formula ##STR1## in which R is H or Ch.sub.3 ##STR2## in which R.sub.1 is H, substituted or unsubstituted C.sub.1 -C.sub.4 -alkyl or --X--YX is a divalent aliphatic, cycloaliphatic, aliphaticcycloaliphatic radical or an araliphatic radicalY is COOH, SO.sub.3 H, OSO.sub.3 H or SO.sub.2 G, in whichG is CH.dbd.CH.sub.2 or --CH.sub.2 --CH.sub.2 --Z, in which Z denotes a group which can be eliminated under alkaline conditions,R.sub.2 is H or C.sub.1 -C.sub.4 -alkyl, and the benzene radical D and the benzene or naphthalene radical L can contain customary substituents,is suitable for the dyeing and printing of OH- and NH-containing materials. They produce lightfast and wetfast brilliant dyeings and prints.Type: GrantFiled: July 11, 1989Date of Patent: December 24, 1991Assignee: Bayer AktiengesellschaftInventor: Horst Jager
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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: 5055566Abstract: A compound of the Formula (1): ##STR1## wherein R is H, SO.sub.3 A, C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy, NO.sub.2, OH or halogen;W, X, Y and Z are independently H or SO.sub.3 A; andA is NQ.sub.4 wherein at least one Q is a branched chain fatty C.sub.6-20 -aliph atic group.Type: GrantFiled: June 19, 1990Date of Patent: October 8, 1991Assignee: Imperial Chemical Industries PLCInventors: Peter Gregory, Ronald W. Kenyon
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Patent number: 5053495Abstract: 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: August 24, 1989Date of Patent: October 1, 1991Assignee: Imperial Chemical Industries PLCInventors: David Greenwood, Nigel Hughes, Ronald W. Kenyon, Suraj L. Hindagolla
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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: 4918169Abstract: Reactive dyes suitable for dyeing and printing cellulosic fiber materials by the cold pad-batch process having the formula ##STR1## wherein Fa is a monoazo or polyazo, metal complex azo, anthraquinone, phthalocyanine, formazane, azomethine, dioxazine, phenazine, stilbene, triphenylmethane, xanthene, thioxanthone, nitroaryl, napthoquinone, pyrenequinone or perylene-tetracarbimide dye radical, X is halogen, C.sub.1 -C.sub.4 -alkylsulfonyl, phenylsulfonyl, a sulfonic acid or phosphonic acid group or a quaternized ammonium group, r is 1 or 2, R is hydrogen or C.sub.1 -C.sub.4 alkyl which is unsubstituted or substituted by halogen, hydroxyl, cyano, carboxyl, sulfo, sulfato, C.sub.1 -C.sub.4 -alkoxycarbonyl, C.sub.1 -C.sub.4 -alkoxy or phenyl, and A is a radical of the formula ##STR2## wherein R' is hydrogen, C.sub.1 -C.sub.4 alkyl which is unsubstituted or substituted by halogen, hydroxyl, cyano, carboxyl, sulfo, sulfato, C.sub.1 -C.sub.4 -alkoxycarbonyl, C.sub.1 -C.sub.4 -alkoxy or phenyl, C.sub.5 -C.sub.Type: GrantFiled: August 19, 1988Date of Patent: April 17, 1990Assignee: Ciba-Geigy CorporationInventor: Karl Hoegerle
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Patent number: 4867789Abstract: A method for purifying a dye solution is provided. The method comprises the steps of dissolving an impure dye in a solvent. A flocculant is then added to the dye solution in order to flocculate the imprity so that the impurity may then be removed from the solution. A method for producing on ink utilizing the purification procedure is also provided.Type: GrantFiled: October 9, 1987Date of Patent: September 19, 1989Assignee: Canon Kabushiki KaishaInventors: Tsuyoshi Eida, Makoto Shioya, Masatsune Kobayashi
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Patent number: 4703113Abstract: 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 & R.sup.2 together with the nitrogen atom form a morpholine ringa & b are different and from 1 to 8m is from 1 to 10;n is from 0 to 9;M is H, ammonium, or a monovalent metal;X (i) NR.sup.1 R.sup.2, (ii) NR.sup.3 R.sup.4, in which R.sup.3 and R.sup.Type: GrantFiled: August 12, 1985Date of Patent: October 27, 1987Assignee: Imperial Chemical Industries PLCInventors: Anthony G. W. Baxter, Stephen B. Bostock, David Greenwood
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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