Two Azo Groups Attached Indirectly To Each Other By Nonionic Bonding Patents (Class 534/797)
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Patent number: 5616694Abstract: A compound of Formula (1) and salts thereof wherein the variables are as defined in the specification:Ar.sup.1 N.dbd.N-J-X-L-X-J-N.dbd.NAr.sup.2 (1)A compound of Formula (1) is suitable for use in the coloration of cellulosic substrates, such as paper, to give bright prints with good light and water fastness. It is especially suitable for use in the printing of paper by non-impact printing techniques, such as ink jet printing, especially thermal ink jet printing.Type: GrantFiled: July 12, 1995Date of Patent: April 1, 1997Assignee: Zeneca LimitedInventors: Ronald W. Kenyon, Prahalad M. Mistry
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Patent number: 5609673Abstract: A recording liquid comprising an aqueous medium and at least one dye selected from dyes, the free acid forms of which are represented by formula (I): ##STR1## All the symbols in formula (I) are defined in the description.Type: GrantFiled: December 12, 1995Date of Patent: March 11, 1997Assignee: Mitsubishi Chemical CorporationInventors: Hiroshi Takimoto, Hideo Sano, Masahiro Yamada
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Patent number: 5571940Abstract: In this method, one attaches one or more chelatant molecules to a mono- or polyamino intermediate compound I which is temporarily immobilized on a solid phase by a splittable bond. Thereafter, said bond is split to release the desired conjugate moiety, whereby a reactive site is generated at the splitting site. The conjugate can be coupled to a protein homing factor using said reactive site; the latter being single per chelatant molecule, undesirable cross-linking during conjugation is substantially avoided.Type: GrantFiled: February 3, 1995Date of Patent: November 5, 1996Assignee: Bracco International B.V.Inventor: Paul Palacios
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Patent number: 5571898Abstract: There are described dyes of the formula ##STR1## where the ring A may be benzofused, R.sup.1 is substituted or unsubstituted C.sub.1 -C.sub.13 -alkyl, substituted or unsubstituted phenyl, C.sub.1 -C.sub.8 -alkanoyl, substituted or unsubstituted benzoyl, substituted C.sub.2 -C.sub.4 -alkanoyl, or substituted diaminotriazinyl,R.sup.2 is hydrogen or C.sub.1 -C.sub.4 -alkyl or R.sup.1 and R.sup.2 together with the nitrogen atom joining them together are a heterocyclic radical,R.sup.3 and R.sup.4 are each substituted or unsubstituted C.sub.1 -C.sub.13 -alkyl, substituted or unsubstituted C.sub.5 -C.sub.7 -cycloalkyl or substituted or unsubstituted piperidinyl and R.sup.3 may also be hydrogen,R.sup.5 is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.2 -C.sub.5 -alkanoylamino, halogen, nitro, cyano, substituted or unsubstituted phenylazo, C.sub.2 -C.sub.4 -alkanoylamino substituted by a quaternizable or quaternary group, or C.sub.2 -C.sub.4 -alkoxy, C.sub.2 -C.sub.4 -alkoxycarbonyl or C.sub.2 -C.Type: GrantFiled: July 11, 1995Date of Patent: November 5, 1996Assignee: BASF AktiengesellschaftInventors: Ulrike Schloesser, Udo Mayer
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Patent number: 5569749Abstract: An organic photoconductive material is represented by the following general formula [1]:A.sub.1 --N.dbd.N--B--N.dbd.N--A.sub.2 [1],wherein B is a divalent organic group bonded to nitrogen atoms forming azo groups, A.sub.1 and A.sub.2 are groups different from each other, A.sub.1 is represented by the following general formula [A1]: ##STR1## wherein X is an atomic group which is necessary for forming an aromatic hydrocarbon ring or an aromatic hetero-ring by condensation with the benzene ring, Y is a hydrogen atom, an alkyl group, an alkoxy group or a halogen atom, m is an integer of 1 to 4, R is an aromatic hydrocarbon ring group or an aromatic hetero-ring group and n is 1 or 2, and A.sub.2 is a group represented by one of the following general formulae [A2] and [A3]: ##STR2## wherein a.sub.1 is a group selected from R, --N.dbd.CH--R and ##STR3## R, X, Y, m and n are the same as those in the general formula [A1] and p is 0 or 1.Type: GrantFiled: January 18, 1996Date of Patent: October 29, 1996Assignee: Dainichiseika Color & Chemicals Mfg. Co., Ltd.Inventors: Hisao Kouno, Shyouichi Takahashi, Kazuhiro Higashide, Nakaji Komiyama, Osamu Suda, Masaru Hasegawa
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Patent number: 5554738Abstract: Anionic disazo dyes useful for dyeing and printing textile materials, paper and leather and for the preparation of inks of the formula ##STR1## wherein D, R.sup.3, R.sup.4, M, R.sup.5 and R.sup.7 are defined as in the specification.Type: GrantFiled: October 18, 1991Date of Patent: September 10, 1996Assignee: Ciba-Geigy CorporationInventors: Jean-Marie Adam, Adolf K aser
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Patent number: 5519121Abstract: Novel dyestuffs of the formula (I) ##STR1## in which DK denotes a radical of the formula ##STR2## where m is 1 or 2 and DK' denotes a radical of the formula ##STR3## where n is 1 or 2 R.sub.1 represents hydrogen or substituted or unsubstituted C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkyl,R.sub.2 represents hydrogen, substituted or unsubstituted C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy,R.sub.3 represents substituted or unsubstituted C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -acylamino andR.sub.4 represents substituted or unsubstituted C.sub.1 -C.sub.4 -alkyl.have now been found.The invention also relates to a process for their preparation and to their use for dyeing/coloring and printing textiles and paper, in particular in printing inks containing these dyestuffs.Type: GrantFiled: February 24, 1995Date of Patent: May 21, 1996Assignee: Bayer AktiengesellschaftInventors: Gerd-Friedrich Renner, Peter Wild, Karin Hassenruck
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Patent number: 5506346Abstract: An organic photoconductive material is represented by the following general formula [1]:A.sub.1 -N.dbd.N-B-N.dbd.N-A.sub.2 [1],wherein B is a divalent organic group bonded to nitrogen atoms forming azo groups, A.sub.1 and A.sub.2 are groups different from each other, A.sub.1 is represented by the following general formula [A1]: ##STR1## wherein X is an atomic group which is necessary for forming an aromatic hydrocarbon ring or an aromatic hetero-ring by condensation with the benzene ring, Y is a hydrogen atom, an alkyl group, an alkoxy group or a halogen atom, m is an integer of 1 to 4, R is an aromatic hydrocarbon ring group or an aromatic hetero-ring group and n is 1 or 2, and A.sub.2 is a group represented by one of the following general formulae [A2] and [A3]: ##STR2## wherein a.sub.1 is a group selected from R, -N.dbd.CH-R and ##STR3## R, X, Y, m and n are the same as those in the general formula [A1] and p is 0 or 1.Type: GrantFiled: February 28, 1994Date of Patent: April 9, 1996Assignee: Dainichiseika Color & Chemicals Mfg. Co., Ltd.Inventors: Hisao Kouno, Shyouichi Takahashi, Kazuhiro Higashide, Nakaji Komiyama, Osamu Suda, Masaru Hasegawa
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Patent number: 5498701Abstract: Basic sulpho group-containing disazo compounds which are metal-free, correspond to the formula ##STR1## in which the symbols are as defined in claim 1. These compounds, in form of their water-soluble salts, and preparations thereof are used for dyeing or printing cationically dyeable materials such as hydroxy group- or nitrogen-containing organic substrates of which textile material comprising natural or synthetic polyamide or natural or regenerated cellulose and especially cotton, leather and paper are preferred. Furthermore, they can be used for the preparation of inks in a conventional manner.Type: GrantFiled: December 22, 1994Date of Patent: March 12, 1996Assignee: Sandoz Ltd.Inventor: Reinhard Pedrazzi
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Patent number: 5493011Abstract: Water-insoluble azo colorants, their preparation and use The invention relates to monoazo and disazo compounds of the formula (I) ##STR1## in which D is the radical of a carbocyclic or heterocyclic diazo or bisdiazo component, R.sup.1 and R.sup.2, independently of one another, are each a substituted or unsubstituted aryl or heteroaryl radical, X.sup.1 and X.sup.2, independently of one another, are each ring-forming ether oxygen or a substituted or unsubstituted imide grouping and n has the value 0 or 1, in which rings A and B, independently of one another, can each be additionally substituted and/or carry substituted or unsubstituted fused rings.These new compounds of the formula (I) are obtained by coupling diazotized amines or diamines of the type D--NH.sub.2 or H.sub.2 N--D--NH.sub.2 with (benzoxazol-2-yl)- or (benzimidazol-2-yl)-arylacetamides.Depending on the presence and length of alkyl chains, the compounds of the formula (I) are suitable for use as pigments, disperse dyes or oil-soluble dyes.Type: GrantFiled: November 6, 1992Date of Patent: February 20, 1996Assignee: Hoechst AGInventors: Rudiger Jung, Reinhold Deubel
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Patent number: 5484899Abstract: The invention relates to compounds of the formula ##STR1## in which the variables are as defined in the claims. The compounds are suitable as dyes, in particular for dyeing and printing cellulosic fibre materials, and produce dyeings and prints with good all-round fastness properties.Type: GrantFiled: May 3, 1994Date of Patent: January 16, 1996Assignee: Ciba-Geigy CorporationInventors: Rolf Deitz, Athanassios Tzikas
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Patent number: 5484898Abstract: The invention relates to compounds of formula ##STR1## wherein the variables are as defined in the claims. The compounds are suitable for use as dyes, especially for dyeing and printing cellulosic fibre materials, and give dyeings and prints of good fastness properties.Type: GrantFiled: May 10, 1994Date of Patent: January 16, 1996Assignee: Ciba-Geigy CorporationInventors: Rolf Deitz, Athanassios Tzikas
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Patent number: 5473053Abstract: A compound of Formula (1) and salts thereof:Ar.sup.1 N.dbd.N--J--X--L--X--J--N.dbd.NAr.sup.2 (1)wherein: ##STR1## Ar.sup.1 and Ar.sup.2 are each independently aryl containing at least two carboxy groups; andL is a group of the Formula (3a) or (3b): ##STR2## in which T.sup.1 and T.sup.2 each independently is C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy or C.sub.3-4 -alkenyl;T.sup.3 and T.sup.4 each independently is H, C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy or C.sub.3-4 -alkenyl provided that T.sup.3 and T.sup.4 are not both H;each X independently is a group of the Formula (4), (5) or (6): ##STR3## each Z independently is H, halogen, alkyl, NR.sup.1 R.sup.2, SR.sup.3 or 0R.sup.3 ;each Y independently is Z, SR.sup.4 or OR.sup.4 ;each E independently is Cl or CN; andR.sup.1, R.sup.2, R.sup.3 and R.sup.4 are each as defined in the specification.A compound of Formula (1) is suitable for use in the coloration of cellulosic substrates, such as paper, to give bright prints with good light and water fastness.Type: GrantFiled: January 7, 1994Date of Patent: December 5, 1995Assignee: Zeneca LimitedInventors: Ronald W. Kenyon, Prahalad M. Mistry
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Patent number: 5466282Abstract: Disclosed herein is a monoazo dye compound having a structural unit represented by the following formula in its molecule:--X--Y--(R.sub.1)(R.sub.2)(R.sub.3).sub.k [I]wherein Y is a 6-membered ring containing 2 or 3 nitrogen atoms, X is a linking group for bonding a main body of the dye molecule to Y, R.sub.1 is the first amino acid residue, R.sub.2 is an atomic group selected from the following group A, R.sub.3 is another atomic group selected from the following group BB, and k is a number of 0 or 1:Group A: H, OH, NH.sub.2, CN, .dbd.O and the second amino acid residue;Group BB: H, OH, NH.sub.2, CN and .dbd.O,the first and second amino acid residues being identical with or different from each other.Type: GrantFiled: May 12, 1994Date of Patent: November 14, 1995Assignee: Canon Kabushiki KaishaInventors: Tsuyoshi Eida, Osamu Nishiwaki, Takao Yamamoto, Kumiko Mafune
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Patent number: 5464941Abstract: The present invention provides novel substituted biphenyl pyrazines or pyrazine derivatives ("BPD") which are functional and have useful application as a monomer for a variety of high performance polymers such as polyester, polyarylate, polycarbonate, polyetherketones, epoxides, polyimides, polyamides, and polyamides-imides; and as pigments for coating compositions such as paints.Type: GrantFiled: October 19, 1994Date of Patent: November 7, 1995Assignee: Hoechst Celanese CorporationInventors: Richard Vicari, George Kvakovszky, Olan S. Fruchey, Hans J. Metz
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Patent number: 5453495Abstract: A compound of Formula (1) and salts thereof: ##STR1## wherein: L is optionally substituted piperazinyl;D is optionally substituted phenylene or naphthylene;E is optionally substituted phenylene, naphthylene or quinoline;R is H or C.sub.1-4 -alkyl;Z is optionally substituted carboxyaryl; andn has a value of 0 or 1.A compound of Formula (1) is useful as a colorant for black inks suitable for ink jet printing.Type: GrantFiled: December 22, 1994Date of Patent: September 26, 1995Assignee: Zeneca LimitedInventors: Peter Gregory, Ronald W. Kenyon, Prahalad M. Mistry
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Patent number: 5420258Abstract: Azo dyes of formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, X, Y and n are as defined in claim 1, give dyeings of good fastness properties on nitrogen-containing or hydroxyl group containing fibre materials.Type: GrantFiled: August 23, 1993Date of Patent: May 30, 1995Assignee: Ciba-Geigy CorporationInventors: Jurgen Schaetzer, James C. Posey
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Patent number: 5383960Abstract: An ink containing less than 5% inorganic compounds which comprises a liquid medium and a dye of the Formula (1): ##STR1## wherein: D.sup.1 and D.sup.2 are each independently a chromophore of the azo series;R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are each independently H or optionally substituted alkyl;B is a labile atom or group, hydroxy, amino or an ether, thioether or amine group; andX.sup.1 and X.sup.2 are each independently H, halo, alkyl, alkoxy, acylamino, ureido, nitro, carboxy or sulpho.The inks may be used in ink jet printing either alone or with specified xanthene dyes.Type: GrantFiled: January 26, 1993Date of Patent: January 24, 1995Assignee: Zeneca LimitedInventors: Peter Gregory, Ronald W. Kenyon, Prahalad M. Mistry, John A. Taylor
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Patent number: 5374301Abstract: An ink comprising a liquid medium and a compound of Formula (1) or salt thereof: ##STR1## provided (i) if the compound of Formula (1) has no --SO.sub.3 H groups then it has at least two groups selected from --COOH and --COSH; and (ii) the compound of Formula (1) has at least as many groups selected from --COOH and --COSH as --SO.sub.3 H groups. The inks are useful for ink-jet printing.Type: GrantFiled: November 30, 1992Date of Patent: December 20, 1994Assignee: Zeneca LimitedInventors: Peter Gregory, Ronald W. Kenyon
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Patent number: 5354849Abstract: Anionic disazo compounds of the formula ##STR1## and salts thereof each cation of which is independently a non-chromophoric cation, and mixtures of such compounds or salts, wherein D is whereinR.sub.4 is hydrogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy or halo,R.sub.1 is hydrogen, C.sub.1-4 alkyl or C.sub.2-4 hydroxyalkyl,R.sub.2 is hydrogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, (C.sub.1-4 alkyl)carbonylamino, (C.sub.1-4 alkoxy)carbonylamino or --NHCONH.sub.2,R.sub.3 is hydrogen, halo, C.sub.1-4 alkyl or C.sub.1-4 alkoxy, and ##STR2## wherein R.sub.5 is chloro, hydroxy or --NHCN,R.sub.6 is hydrogen, chloro or cyano, andR.sub.7 and R.sub.8 are as defined in the specification, with the proviso that R.sub.7 and R.sub.8 together contain at least 8 carbon atoms,useful for dyeing or printing anionically dyeable organic substrates such as nitrogen-containing substrates, particularly fiber material comprising natural or synthetic polyamide.Type: GrantFiled: June 4, 1993Date of Patent: October 11, 1994Assignee: Sandoz Ltd.Inventor: Georg Schoefberger
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Patent number: 5328995Abstract: The compounds of the formula ##STR1## where the substituents are as defined in claim 1, are direct dyes for various substrates, in particular cellulosic fibre materials. They are high temperature resistant and therefore are particularly highly suitable for the one-bath, single-stage dyeing of polyester/cotton blend fabrics with a disperse dye for the polyester fibres under the dyeing conditions for polyester fibres.Type: GrantFiled: January 27, 1993Date of Patent: July 12, 1994Assignee: Ciba-Geigy CorporationInventors: Rudolf Schaulin, Urs Lauk
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Patent number: 5268459Abstract: Anionic azo compounds which, in the free acid form, have the Formula (1): ##STR1## wherein: Ar and Ar.sup.1 are each independently aryl or substituted aryl providing at least one of Ar and Ar.sup.1 has at least one substituent selected from COOH and COSH;J and J.sup.1 are each independently of formula (2), (3) or (4): ##STR2## each R.sup.5 is independently selected from H, alkyl, substituted alkyl, alkoxy, halogen, CN, ureido and NHCOR.sup.6 ;R.sup.6 is H, alkyl, substituted alkyl, aryl, substituted aryl, aralkyl or substituted aralkyl;each T is independently alkyl;each W is independently selected from H, CN, CONR.sup.10 R.sup.11, pyridinium and COOH;each m is an alkylene chain having 2 to 8 carbon atoms;B is H, alkyl or COOH;R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.10 and R.sup.11 are each independently H, alkyl or substituted alkyl;L is a divalent organic linking group;n is 0 or 1;each X is independently carbonyl or a group of the Formula (5), (6) or (7): ##STR3## Z is OR.sup.7, SR.sup.7 or NR.sup.8 R.sup.Type: GrantFiled: June 28, 1991Date of Patent: December 7, 1993Assignee: Imperial Chemical Industries plcInventors: Peter Gregory, Ronald W. Kenyon
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Patent number: 5262527Abstract: Anionic azo compounds which, in the free acid form, have the Formula (1): ##STR1## Ar.sup.1 and Ar.sup.2 are each independently aryl or substituted aryl providing at least one of Ar.sup.1 and Ar.sup.2 has at least one substituent selected from COOH and COSH;each R.sup.1 and R.sup.2 is independently H, alkyl, substituted alkyl, alkenyl or substituted alkenyl;L is a divalent organic linking group;n is 0 or 1;each X independently is carbonyl or a group of the formula (2), (3) or (4): ##STR2## each Z independently is NR.sup.3 R.sup.4, SR.sup.5 or OR.sup.5 ; each Y independently is H, Cl, Z, SR.sup.6 or OR.sup.6 ;each E independently is Cl or CN;R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are each independently H, alkyl, substituted alkyl, alkenyl, substituted alkenyl, aryl, substituted aryl, aralkyl, substituted aralkyl or R.sup.3 and R.sup.Type: GrantFiled: June 28, 1991Date of Patent: November 16, 1993Assignee: Imperial Chemical Industries PLCInventors: Peter Gregory, Ronald W. Kenyon, Prahalad M. Mistry
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Patent number: 5225545Abstract: The compounds of the formula (1) indicated in claim 1 are suitable for use as direct dyes for dyeing and printing a wide range of materials, in particular cellulose-containing fibre materials, producing dyeings and prints having good fastness properties.Type: GrantFiled: May 12, 1992Date of Patent: July 6, 1993Assignee: Ciba-Geigy CorporationInventor: Urs Lauk
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Patent number: 5183501Abstract: An ink composition for ink jet recording, which contains a water-soluble dye, an organic solvent and water, in which the dye is represented by the formula (1) as shown in the state of free acid:D--(SO.sub.2 CH.sub.2 CH.sub.2 SO.sub.3 H).sub.m (1)wherein D represents a dye residue selected from the group of monoazo and polyazo dyes, their complexes with Cr, Fe, Co and Cu, copper and nickel phthalocyanine dyes, anthraquinone dyes, dioxazine dyes, and formazane complex dyes, and m represents an integer of 1, 2, 3 or 4, and which is superior in its stability during preservation and while being used, thermal stability, image clearness, water resistivity, light fastness, etc.Type: GrantFiled: October 11, 1991Date of Patent: February 2, 1993Assignees: Sumitomo Chemical Company, Limited, Taoka Chemical Co. Ltd.Inventors: Hideo Kawashita, Mituhiro Ohta, Kazuya Ogino
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Patent number: 5019165Abstract: A recording fluid for the ink jet process contains a water-miscible organic solvent and a dye of the formula ##STR1## where R.sup.1 and R.sup.2 are each independently of the other hydrogen, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy,A.sup..crclbar. is an anion andX is a bridge member of the formula ##STR2## where R.sup.3 is chlorine, hydroxy, C.sub.1 -C.sub.6 -alkoxy, amino, C.sub.1 -C.sub.4 -monoalkyl- or dialkyl-amino, anilino, N-(C.sub.1 -C.sub.4 -alkyl)anilino, pyrrolidino, piperidino, morpholino, piperazino or N-(C.sub.1 -C.sub.4 -alkyl)piperazino.Type: GrantFiled: December 30, 1988Date of Patent: May 28, 1991Assignee: BASF AktiengesellschaftInventors: Horst Bruder, Udo Mayer
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Patent number: 5006128Abstract: Compounds of the formula ##STR1## and salts thereof, whereinR.sub.1 is hydrogen or methyl,R.sub.2 is hydrogen, methyl or acetamido,R.sub.3 is hydrogen, methyl or methoxy,R.sub.4 is hydrogen, C.sub.1-4 alkyl or hydroxy(C.sub.2-4 alkyl),R.sub.5 is hydroxy(C.sub.2-4 alkyl) or hydroxy(C.sub.2-4 alkoxy)C.sub.2-4 alkyl, or--NR.sub.4 R.sub.5 is a 5- or 6-membered ring containing 1 to 3 hetero atoms which ring is unsubstituted or substituted by 1 to 3 substituents selected from C.sub.1-4 alkyl and C.sub.2-4 alkyl monosubstituted by hydroxy or amino, andthe two naphthyl-2 groups are identically substituted, with the proviso that when R.sub.3 is methoxy, R.sub.1 and R.sub.2 are different, solid and aqueous liquid dye compositions and printing inks comprising such compounds and salts and the use of such compounds and salts for dyeing and printing substrates, especially hydroxy group- and nitrogen-containing organic substrates.Type: GrantFiled: August 25, 1989Date of Patent: April 9, 1991Assignee: Sandoz Ltd.Inventor: Reinhard Pedrazzi
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Patent number: 4997919Abstract: This invention relates to direct dyes for various substrates, in particular cellulosic fiber materials. The inventive dyes are high-temperature-resistant and highly suitable for the single bath, one step dyeing of polyester/cotton mixed fabrics with a disperse dye for the polyester fibers under the dyeing conditions for polyester fibers.The inventive dyes are of the formula ##STR1## in which A is a radical of the formula ##STR2## A' has the meaning of A or is a mono- or polyazo dye radical which is different from A, R and R', independently of one another, are hydrogen or C.sub.1 -C.sub.4 alkyl which is unsubstituted or substituted by chlorine, hydroxyl, cyano, carboxyl, sulfo, sulfato, methoxy, ethoxy, methoxycarbonyl or ethoxycarbonyl, R.sub.1 is hydroxyl, C.sub.1 -C.sub.4 alkoxy, halogen, C.sub.1 -C.sub.4 alkylthio, amino, N-mono- or N,N-di-C.sub.1 -C.sub.4 alkylamino which is unsubstituted or substituted in the alkyl moiety by hydroxyl, carboxyl or C.sub.1 -C.sub.Type: GrantFiled: June 19, 1989Date of Patent: March 5, 1991Assignee: Ciba-Geigy CorporationInventor: Rudolf Schaulin
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Patent number: 4975118Abstract: A recording fluid for the ink jet process contains a water-miscible organic solvent and a dye of the formula ##STR1## where m is 0 or 1,D.sup.1 and D.sup.2 are each independently of the other the radical of a diazocomponent of the aniline series,R.sup.1 is hydrogen or C.sub.1 -C.sub.4 -alkyl andR.sup.2 and R.sup.3 are each independently of the other a radical having an external basic group.Type: GrantFiled: January 27, 1989Date of Patent: December 4, 1990Assignee: BASF AktiengesellschaftInventors: Udo Mayer, Rainer Dyllick-Brenzinger, Horst Bruder, Steven J. Bares
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Patent number: 4968784Abstract: Disazo compounds represented by the following formula (I): ##STR1## in which R.sub.1 and R.sub.2 are hydrogen, C.sub.1-3 alkyl, C.sub.1-4 alkoxy C.sub.1-3 alkyl, phenyl C.sub.1-3 alkyl, phenoxy C.sub.1-3 alkyl, hydroxy C.sub.1-3 alkyl, cyano C.sub.1-3 alkyl, C.sub.1-4 alkoxyhydroxy C.sub.1-3 alkyl or hydroxyphenoxy C.sub.1-3 alkyl,R.sub.3 is C.sub.1-4 alkyl,R.sub.4 is methyl or ethyl,R.sub.5 is hydrogen, chlorine, methyl or methoxy,n is 2 or 3 respectivelyin the form of the free acid is disclosed and these present compounds are used for dyeing of various fibre materials, leather, wood, pulp and paper etc. in black shade and preparing of black ink for ink-jet, felt-pen and signpen etc. The present compounds have high color value, high affinity and high dyeing velocity on paper and excellent fastnesses.Type: GrantFiled: May 31, 1989Date of Patent: November 6, 1990Assignee: Nippon Kayaku Kabushiki KaishaInventors: Hidenori Imai, Masahiro Hiraki, Yoshiaki Shimizu
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Patent number: 4956457Abstract: The new azo compounds are represented by the following general formula I ##STR1## Wherein R and R.sup.1 are hydrogen, --COCR.sub.3.sup.4 --COCHR.sub.2.sup.4, --SO.sub.2 CH.sub.3, --CO.sub.2 C.sub.2 H.sub.5, --CH.sub.2 CH.sub.2 R.sup.4, --( CH.sub.2 CH.sub.2 R.sup.4).sub.2, --CH.sub.2 CH.sub.2 OH, --CONHCH.sub.2 CH.sub.2 R.sup.4 or --CH.sub.2 CH.sub.2 OCONH.sub.2 and R.sup.4 is Cl or a group of the formula ##STR2## --NHCO.sub.2 CH.sub.3 CH.sub.2 OH, --NHCO.sub.2 C.sub.2 H.sub.5, --NHOH, --NHCONHOH, or --NHCH.sub.3, whereby R.sup.1 and R.sup.2 are similar or dissimilar.Type: GrantFiled: August 10, 1989Date of Patent: September 11, 1990Inventor: Takeo Takayanagi
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Patent number: 4917981Abstract: A photosensitive member for electrophotography which comprises a photosensitive layer containing at least one member of the group consisting of thiophene structure-containing azo compounds having one of the general formulae (I) to (X): ##STR1## wherein all the symbols are defined in the specification.Type: GrantFiled: December 28, 1987Date of Patent: April 17, 1990Assignee: Fuji Electric Co., Ltd.Inventors: Yoichi Nakamura, Masami Kuroda, Noboru Furusho
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Patent number: 4908062Abstract: A water-soluble dye, free from cellulose reactive groups, of the formula: ##STR1## wherein each of Ar.sup.1 and Ar.sup.2, independently, represents an optionally substituted phenyl or naphthyl radical,each of R.sup.1 and R.sup.4, independently, represents --OR.sup.5 or --NR.sup.6 R.sup.7,R.sup.5 represents hydrogen or alkyl,R.sup.6 represents hydrogen, alkyl, aryl or a radical of the formula --(C.sub.a H.sub.2a O).sub.m (C.sub.b H.sub.2b O).sub.n H,R.sup.7 represents hydrogen, alkyl, aryl, a radical fo the formula --(C.sub.a H.sub.2a O).sub.m (C.sub.b H.sub.2b O).sub.n H or a radical of a mono- or disazo dye, orR.sup.6 and R.sup.7 together form a morpholine ring,a and b are different integers from 1 to 8,m is an integer from 1 to 10,n is an integer from 0 to 9,each of R.sup.2 and R.sup.3, independently, represents hydrogen or alkyl,M represents hydrogen, ammonium or a monovalent metal, and each of p and q, independently is an integer from 1 to 3.The dyes are suitable for use in ink jet printing.Type: GrantFiled: January 9, 1989Date of Patent: March 13, 1990Assignee: Imperial Chemical Industries PLCInventors: Brian Balmforth, Nigel Hughes
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Patent number: 4866163Abstract: Compounds of the formula ##STR1## wherein each R.sub.1 is independently hydrogen, halo, C.sub.1-4 alkyl, C.sub.1-4 alkoxy or --NHCOC.sub.1-4 alkyl, each R.sub.2 is H, halo, C.sub.1-4 alkyl or C.sub.1-4 alkoxy, each R.sub.3 is independently halo, hydroxy, C.sub.1-4 alkoxy, --NHOH, amino or an aliphatic, aromatic cycloaliphatic or saturated heterocyclic amino radical, and is divalent aliphatic or aromatic group or, together with the NH radicals to which it is attached, forms a piperazine ring, and the use thereof for dyeing or printing hydroxy group- or nitrogen-containing organic substrates after which the dyed or printed substrate is optionally treated with a cationic fixing agent.Type: GrantFiled: May 2, 1984Date of Patent: September 12, 1989Assignee: Sandoz, Ltd.Inventor: Werner Koch
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Patent number: 4841034Abstract: Water-soluble metallized disazo compounds which, in the free acid form, are represented by the following formula: ##STR1## wherein R.sub.1 and R.sub.2 stand independently for chlorine or nitro, and X stands for phenyl which may be substituted with chlorine, methyl, lower alkoxy, hydroxyl or carboxyl, for use in dyeing.Type: GrantFiled: November 15, 1984Date of Patent: June 20, 1989Assignee: Nippon Kayaku Kabushiki KaishaInventors: Satoshi Ototake, Ryozo Matsunaga, Masao Furusawa
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Patent number: 4839468Abstract: Triazine compounds which in their betaine form correspond to the formula ##STR1## wherein Y denotes hydrogen or the radical of an azo dye-stuff,R denotes hydrogen or alkyl,Ar denotes arylene,Z denotes halogen, hydroxyl, alkoxy, alkyl, aryl or an amino group which may be monosubstituted or disubstituted,m denotes 0 or 1 andX.sup.(+) denotes an ammonium groupamd whereimthe cyclic and acyclic radicals can carry further substituents,are used for dyeing/coloring natural and synthetic substrates and compositions, in particular paper.Type: GrantFiled: November 13, 1984Date of Patent: June 13, 1989Assignee: Bayer AktiengesellschaftInventors: Horst Nickel, Peter Wild, Frank-Michael Stohr
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Patent number: 4799960Abstract: A water-soluble dye, free from cellulose reactive groups, of the formula: ##STR1## wherein R.sup.1 is --(C.sub.a H.sub.2a O).sub.m (C.sub.b H.sub.2b O) .sub.n H,R.sup.2 is H or --(C.sub.a H.sub.2a O).sub.m (C.sub.b H.sub.2b O).sub.n H, orR.sup.1 and R.sup.2 together with the nitrogen atom form a morpholine ringa and b are different and from 1 to 8m is from 1 to 10;n is from 0 to 9;q is 1/2 or 1p is 1 or 2L is a transition metal capable of complexing with a dyeM is H, ammonium, or a monovalent metal;Q is H or SO.sub.3 MT is H or C.sub.1-4 -alkyl;D is a substituted azo group;B, E and F are H or substituents;X is NR.sup.1 R.sup.2, NR.sup.3 R.sup.4, --NR.sup.3 --Z--NR.sup.4 --, OR.sup.3, or the residue of a mono- or bis-azo chromophore comprising benzene, naphthalene or mono- or bi- cyclic heteroaryl diazo and coupling components, linked to the triazine nucleus through a primary or secondary amine linking group, wherein R.sup.3 & R.sup.Type: GrantFiled: November 10, 1986Date of Patent: January 24, 1989Assignee: Canon Kabushiki KaishaInventors: Anthony G. W. Baxter, Stephen B. Bostock, David Greenwood
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Patent number: 4780532Abstract: 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;q is 1/2 or 1p is 1 or 2L is a transition metal capable of complexing with a dyeM is H, ammonium, or a monovalent metal;B, D, F & E are H or substituents;X is NR.sup.1 R.sup.2, NR.sup.3 R.sup.4, --NR.sup.3 --Z--NR.sup.4 --, OR.sup.3, or the residue of a mono- or dis-azo chromophore comprising benzene, naphthalene or hetero-mono- or bi-cyclic diazo and coupling components, linked to the triazine nucleus through a primary or secondary amino linking group in which R.sup.3 and R.sup.Type: GrantFiled: August 12, 1985Date of Patent: October 25, 1988Assignee: Imperial Chemical Industries PLCInventors: Anthony G. W. Baxter, Stephen B. Bostock, David Greenwood
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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: 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: 4746733Abstract: 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 ring;a & b are different and from 1 to 8;m is from 1 to 10;n is from 0 to 9;Y is a triphendioxazinylene (TPD) group;M is H, ammonium, or a metal;X is NR.sup.1 R.sup.2, alkoxy, NR.sup.3 R.sup.4 in which R.sup.3 and R.sup.4 are each independently selected from H, alkyl, aryl and heteroaryl, or the residue of a mono- or dis-azo chromophore comprising benzene, naphthalene or mono- or bi-cyclic heteroaryl diazo and coupling components, linked to the triazine nucleus through a primary or secondary amine linking group;andZ is an alkylene, arylene or aralkylene group,suitable for the preparation of a printing ink, especially for ink jet printing.Type: GrantFiled: August 12, 1985Date of Patent: May 24, 1988Assignee: Imperial Chemical Industries PLCInventors: Anthony G. W. Baxter, Stephen B. Bostock, David Greenwood
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Patent number: 4742160Abstract: Metal-free compounds of the formula ##STR1## and 1:1 and 1:2 metal complexes thereof, and salts of the metal-free compounds and 1:1 and 1:2 metal complexes, whereR is hydrogen, --SO.sub.3 H or --NR.sub.5 R.sub.6 ;R.sub.a is hydrogen or --NR.sub.5 R.sub.6 ;R.sub.1 is hydrogen, halogen, --OH, C.sub.1-4 alkyl, C.sub.1-4 alkoxy or --SO.sub.3 H;R.sub.3 is hydrogen or C.sub.1-4 alkyl;R.sub.4 is halogen, --OH, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, phenyl, --NH.sub.2, an aliphatic, cycloaliphatic or aromatic amino group, a heterocyclic amino group containing 1 to 3 hereto atoms or a hydrazino group,R.sub.5 is hydrogen or C.sub.1-4 alkyl; andR.sub.6 is an organic radical, are useful as cationic dyes for dyeing and printing fibers, threads and textile materials comprising, for example, a natural or regenerated cellulosic material such as cotton, a modified synthetic polyamide or polyester, and a homo- or co-polymer of acrylonitrile or 1,1-dicyanoethylene, bast fibers such as hemp and particularly paper and leather.Type: GrantFiled: February 28, 1986Date of Patent: May 3, 1988Assignee: Sandoz Ltd.Inventors: Jacky Dore, Reinhard Pedrazzi
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Patent number: 4734218Abstract: Provided are novel dichroic azo dyestuffs, which contain skeletons represented by the following general formula: ##STR1## at one terminals of the long axes of the molecules of the azo dyestuffs, and liquid crystal compositions containing the dichroic azo dyestuffs in forms dissolved in liquid crystals. These dichroic azo dyestuffs have large dichroic ratios and high durability, and their compositions are employed as useful display devices.Type: GrantFiled: July 18, 1986Date of Patent: March 29, 1988Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Keisuke Takuma, Kimitoshi Kato, Hiroshi Aiga, Yasuyuki Yamada, Tsutomu Nishizawa
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Patent number: 4705528Abstract: 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;q is 1/2 or 1p is 1 or 2L is a transition metal capable of complexing with a dyeM is H, ammonium, or a monovalent metal;Q is H or SO.sub.3 MT is H or C.sub.1-4 -alkyl;D is a substituted azo group;B, E & F are H or substituents;X is NR.sup.1 R.sup.2, NR.sup.3 R.sup.4, --NR.sup.3 --Z--NR.sup.4 --, Or.sup.3, or the residue of a mono- or bis-azo chromophore comprising benzene, naphthalene or mono- or bi- cyclic heteroaryl diazo and coupling components, linked to the triazine nucleus through a primary or secondary amine linking group, wherein R.sup.3 & R.sup.Type: GrantFiled: August 12, 1985Date of Patent: November 10, 1987Assignee: Imperial Chemical Industries PLCInventors: Anthony G. W. Baxter, Stephen B. Bostock, David Greenwood
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Patent number: 4678497Abstract: Triazine-substituted azobenzenesulfonamides useful as preemergent and postemergent herbicides, selected from compounds of Formulae I or II ##STR1## or agriculturally suitable salts thereof, wherein R, R.sub.1, R.sub.2, R.sub.3 and A are as defined herein.Type: GrantFiled: January 13, 1986Date of Patent: July 7, 1987Assignee: E. I. Du Pont de Nemours and CompanyInventor: Wallace C. Petersen
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Patent number: 4667019Abstract: Compounds of the general formula I ##STR1## where n is 0, 1 or 2, R.sup.1 and R.sup.2 are each hydrogen, unsubstituted or substituted alkyl, cycloalkyl, aralkyl, aryl, acyl, alkoxycarbonyl or aryloxycarbonyl, or together form alkylene or an unsubstituted or substituted benzo ring and Y is a radical of the formula ##STR2## where the rings A, B and C can be further substituted or benzo-fused, R.sup.3 and R.sup.4 are each hydrogen or unsubstituted or substituted alkyl, aralkyl or cycloalkyl, or, together with the nitrogen, form piperidino, pyrrolidino or morpholino, R.sup.5 is hydrogen, unsubstituted or substituted alkyl, cycloalkyl, aralkyl, acyl, alkoxycarbonyl, aryloxycarbonyl, alkylsulfonyl, or arylsulfonyl and R.sup.6 is hydrogen, alkyl or cycloalkyl. These compounds are useful as pleochroic dyes and have a good degree of order coupled with high solubility and good stability in the liquid crystal matrix.Type: GrantFiled: January 13, 1986Date of Patent: May 19, 1987Assignee: Kernforschungszentrum Karlsruhe GmbHInventors: Karl-Heinz Etzbach, Peter Neumann
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Patent number: 4667020Abstract: Compounds of the formula ##STR1## where X is a 5-membered heterocyclic structure from the oxazole, oxadiazole, thiazole, thiadiazole, imidazole or triazole series, Y is a radical of the formula ##STR2## the rings A, B and C can be further substituted and can be fused to a benzene ring, R.sup.1 and R.sup.2 are each hydrogen or unsubstituted or substituted alkyl, aralkyl or cycloalkyl, or R.sup.1 and R.sup.2 together with the nitrogen are piperidino, pyrrolidino or morpholino, R.sup.3 is hydrogen or unsubstituted or substituted alkyl, cycloalkyl, aralkyl, acyl, alkoxycarbonyl, aryloxycarbonyl or arylsulfonyl, and R.sup.4 is hydrogen, alkyl or cycloalkyl, are particularly useful as dyes in liquid-crystalline media.Type: GrantFiled: February 20, 1985Date of Patent: May 19, 1987Assignee: BASF AktiengesellschaftInventors: Karl-Heinz Etzbach, Christos Vamvakaris
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Patent number: 4666805Abstract: The present invention relates to a novel disazo compound having the following general formula (I), ##STR1## wherein A represents ##STR2## (wherein R represents an alkyl, alkoxy, nitro, halogen, cyano or halomethyl group; n represents an integer of 0, 1, 2 or 3; and R may be the same or different when n is an integer of 2 or 3), and a method for preparing the same.The present invention further relates to a photosensitive material for use in electrophotography, characterized by providing a photosensitive layer containing a disazo pigment having the following general formula (VII), ##STR3## wherein A.sub.1 represents a coupler residue and R' represents hydrogen or a lower alkyl group.Type: GrantFiled: June 11, 1985Date of Patent: May 19, 1987Assignee: Ricoh Co., Ltd.Inventor: Mitsuru Hashimoto
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Patent number: 4663442Abstract: A disazo compound, having the general formula, ##STR1## wherein Y represents a substituted or non-substituted cyclic hydrocarbon or substituted or non-substituted heterocycle; R represents hydrogen, substituted or non-substituted alkyl group, or substituted or non-substituted phenyl group; andZ represents a substituted or non-substituted cyclic hydrocarbon or heterocycle fused with phenyl nucleus.Type: GrantFiled: July 18, 1985Date of Patent: May 5, 1987Assignee: Ricoh Co., Ltd.Inventor: Masafumi Ohta
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Patent number: 4654384Abstract: Novel water-soluble triazine compounds of the formula ##STR1## in which D and D.sub.1 independently of one another are radicals of diazo components, R and R.sub.1 independently of one another are hydrogen or C.sub.1 -C.sub.4 -aklyl, X is a monosubstituted or disubstituted amino group, a C.sub.1 -C.sub.4 -alkoxy group or an aryloxy group, the symbols Y are basic or cationic groups, which can be identical or different, l is 2, 3, 4, 5 or 6 and n is 0 or 1, and the number of basic and/or cationic groups Y in the molecule must be equal to or greater than the number of SO.sub.3 H groups are useful as dyes for dyeing and printing textile materials, leather and in particular, paper. The dyeings have good general fastness properties and the effluents remain colorless.Type: GrantFiled: January 12, 1984Date of Patent: March 31, 1987Assignee: Ciba-Geigy CorporationInventors: Visvanathan Ramanathan, Peter Mockli