Plural Diazo Or Diazonium Groups Patents (Class 534/561)
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Patent number: 10669425Abstract: A one-pot synthesis for preparing an aqueous reactive black mixture includes a) dissolving 2-[(4-aminophenyl)sulfonyl]ethanesulfonic acid (vinyl sulphone parabase ester) in water; b) diazotizing the dissolved vinyl sulphone parabase ester using excess nitrous acid or using excess nitrite and an acid, resulting in a diazonium salt and remaining nitrous acid; c) quenching the remaining nitrous acid with sulfamic acid; d) coupling the diazonium salt of step c) with 4-amino-5-hydroxy-2,7-naphthalenedisulfonic acid (H-acid) until the reaction is complete, resulting in Reactive Black 5 (RB 5) and remaining diazonium salt, e) coupling the remaining diazonium salt with 7-acetamido-4-hydroxy-2-naphthalenesulfonic acid (acetyl-J-acid) until the reaction is complete resulting in Reactive Orange 78 (RO 78); and f) obtaining the aqueous reactive black mixture.Type: GrantFiled: May 1, 2018Date of Patent: June 2, 2020Assignee: SPGPrints B.V.Inventors: Dennis Manuel Vriezema, Sigrid Elisabeth Kleine, Martin Jan Smallegange
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Patent number: 10319523Abstract: A composite polymeric material includes one or more repeating backbone units; one or more polarizable units incorporated into or connected to one or more of the one or more repeating backbone units; and one or more resistive tails connected to one or more of the repeating backbone units or to the one or more polarizable units as a side chain on the polarizable unit, on a hydrocarbon chain linking a polarizable unit to a backbone unit, or directly attached to a backbone unit. The composite polymeric material may be used to form a metadielectric, which may be sandwiched between to electrodes to form a metacapacitor.Type: GrantFiled: September 20, 2017Date of Patent: June 11, 2019Assignee: CAPACITOR SCIENCES INCORPORATEDInventors: Yan Li, Pavel Ivan Lazarev, Paul T. Furuta, Barry K. Sharp, Samuel Hein
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Publication number: 20150015931Abstract: This invention relates to electrowetting fluids, the use of these fluids for the preparation of an electrowetting displays devices, and electrowetting display devices comprising such fluids.Type: ApplicationFiled: February 12, 2013Publication date: January 15, 2015Applicant: Merck Patent GmbHInventors: Louise Diane Farrand, Nathan Smith, Roshan Kumar, Anthony Lawrence
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Publication number: 20130323640Abstract: Embodiments in accordance with the present invention provide for norbornane-type ballast materials, norbornane-type photoactive compounds derived from such ballast materials and alkali-soluble positive-tone polymer compositions that encompass such norbornane-type photoactive compounds and one of a PBO or PNB resin.Type: ApplicationFiled: August 9, 2013Publication date: December 5, 2013Applicants: Sumitomo Bakelite Co., Ltd., Promerus, LLCInventors: Andrew Bell, Keitaro Seto, Hiroaki Makabe
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Publication number: 20130189574Abstract: The invention relates to a diazonium aryl salt devoid of hydroxyl functions of the following general formula (1): X?+N?N-A-R1—(OR2)n—O—R4-A?-N?N+X???(1) in which: n is an integer comprised between 1 and 10, preferably between 1 and 4, X— represents a counter-ion of the diazonium cation chosen from the halogenides, BF4-, NO3-, HSO4-, PF6-, CH3COO—, N(SO2CF3)2-, CF3SO3-, CH3SO3-, CF3COO—, (CH3O)(H)PO2-, N(CN)2-, R1, R2 and R4 are identical or different and chosen independently from the group formed by —CH2-, a cyclic or acyclic, linear or branched alkyl chain and, A? and A? are identical or different and independently represent a mono or polycyclic, aromatic hydrocarbonated group chosen from the group formed by phenyl, aryl groups, condensed polyaromatic groups, which may be substituted.Type: ApplicationFiled: September 19, 2011Publication date: July 25, 2013Applicants: COMMISSARIAT A L' ENERGIE ATOMIQUE ET AUX ENERGIES ALTERNATIVES, UNIVERSITE JOSEPH FOURIER, CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUEInventors: Laureline Crepel, Fannie Alloin, Jean-Claude Lepretre, Sebastien Martinet
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Patent number: 8410255Abstract: The present invention provides a family of dark quenchers, termed Black Hole Quenchers (“BHQs”), that are efficient quenchers of excited state energy but which are themselves substantially non-fluorescent. Also provided are methods of using the BHQs, probes incorporating the BHQs and methods of using the probes.Type: GrantFiled: August 6, 2010Date of Patent: April 2, 2013Assignee: Biosearch Technologies, Inc.Inventors: Ronald M. Cook, Matt Lyttle, Daren Dick
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Patent number: 8034174Abstract: A diarylide yellow pigment formed by a coupling reaction of a benzidine and a mixture comprising 4-chloro-2,5-dimethoxy-acetoacetanilide and 2,4-dimethyl-acetoacetanilide. The diarylide yellow pigment has a desirable reddish shade than C.I. Pigment Yellow 83, exists in a solid solution, and contains fewer aromatic amine impurities.Type: GrantFiled: April 17, 2009Date of Patent: October 11, 2011Assignee: Sun Chemical CorporationInventors: Russell Schwartz, Ulrik Cassias, Palle Chris Nielsen
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Publication number: 20110245462Abstract: Bis-diazo, triaryl and aryldiazo-N-arylphenazonium quencher moieties, substituted with electron-withdrawing and electron-donating substituents which induce polarity in the delocalized aryl/diazo ring systems, are useful as labels when attached to biomolecules such as polynucleotides, nucleosides, nucleotides and polypeptides. The quencher moieties are non-fluorescent and accept energy transfer from fluorescent reporter labels by any energy-transfer mechanism, such as FRET. Fluorescence quencher compositions are useful in preparing quencher labeled biomolecules for various molecular biology assays based on fluorescence detection.Type: ApplicationFiled: December 16, 2010Publication date: October 6, 2011Applicant: LIFE TECHNOLOGIES CORPORATIONInventors: Gregory J. Ewing, Deborah Kay Fieri, Khairuzzaman Bashar Mullah, Ronald J. Graham
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Publication number: 20110204303Abstract: Disclosed herein are a near-infrared absorbing and color compensation film composition and a film using the film composition. The film composition comprises i) at least one colorant selected from the group consisting of an ionic compound of a near-infrared absorbing cyanine colorant cation having a maximum absorption wavelength in the range of 820 nm to 950 nm and a metal complex colorant anion, an ionic compound of a near-infrared absorbing diimmonium colorant cation having a maximum absorption wavelength in the range of 950 nm to 1,100 nm and a metal complex colorant anion, and an ionic compound of a selective visible light absorbing cyanine colorant cation having a maximum absorption wavelength in the range of 580 nm to 600 nm and a metal complex colorant anion, and ii) an adhesive; and a film using the film composition. When the film composition is used to produce an adhesive film or an antireflective composite film, the price of raw materials used and the number of production steps can be reduced.Type: ApplicationFiled: April 29, 2011Publication date: August 25, 2011Applicant: CHEIL INDUSTRIES, INC.Inventors: Hwi Min SEO, Soo Jeong Lee
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Patent number: 7927384Abstract: Compounds of the general formula (I) a process for their preparation and their use for dyeing and/or printing organic substrates are described.Type: GrantFiled: June 21, 2007Date of Patent: April 19, 2011Assignee: Clariant Finance (BVI) LimitedInventor: Rainer Nusser
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Patent number: 6783539Abstract: A phototriggerable composition and method for use in crosslinking protein such as collagen comprising application of a tethered diazopyruvate composition followed by irradiation, whereby the composition results in the sutureless wound closure of, for example, a tendon or cornea.Type: GrantFiled: March 29, 2002Date of Patent: August 31, 2004Assignee: University of Kansas Medical CenterInventors: George T. Timberlake, Richard S. Givens, Peter G. Conrad, II
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Patent number: 6504045Abstract: The invention relates to six new crystal polymorphs, &agr; (alpha), &bgr; (beta), &ggr; (gamma), &dgr; (delta), &zgr; (zeta), and &eegr; (eta), of the disazo colorant of the formula I, having characteristic reflections in the X-ray diffraction spectrum. The novel crystal polymorphs are prepared by treatment in organic solvents.Type: GrantFiled: September 13, 2001Date of Patent: January 7, 2003Assignee: Clariant GmbHInventors: Ruediger Jung, Hans-Joachim Metz, Joachim Weber, Martin U. Schmidt, Olaf Schupp, Andreas Wacker
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Patent number: 6448384Abstract: An electrophotographic photoconductor has an electroconductive support, and a photoconductive layer formed thereon which contains at least one bisazo compound of formula (I): wherein Cp1 and Cp2 are each a coupler radical which may be the same or different. Further, these are disclosed a bisazo compound of formula (II), and raw materials thereof, that is, 1,4-bis[4-(4-nitrophenyl)-1,3-butadienyl]benzene of formula (V), 1,4-bis[4-(4-aminophenyl)-1,3-butadienyl]benzene of formula (VI) and a bis(diazonium salt) compound of formula (III).Type: GrantFiled: September 4, 2001Date of Patent: September 10, 2002Assignee: Ricoh Company, Ltd.Inventor: Tomoyuki Shimada
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Patent number: 6153733Abstract: Disclosed is a poly(disulfonyl diazomethane) compound as a class of novel compounds represented by the general formula ##STR1## in which the subscript n is 1 to 5, each R is a monovalent hydrocarbon group and Z is a divalent hydrocarbon group. The invention also discloses a chemical-amplification positive-working photoresist composition which comprises the above mentioned poly(disulfonyl diazomethane) compound as the radiation-sensitive acid-generating agent in combination with a film-forming resin capable of being imparted with increased solubility in an aqueous alkaline solution by the interaction with an acid, such as a polyhydroxystyrene resin of which a part of the hydroxyl groups are substituted by acid-dissociable solubility-reducing groups, e.g., tert-butoxycarbonyl groups.Type: GrantFiled: May 13, 1999Date of Patent: November 28, 2000Assignees: Tokyo Ohka Kogyo Co., Ltd., Daito Chemix CorporationInventors: Hiroto Yukawa, Waki Ohkubo, Kouki Tamura, Toshiharu Shimamaki, Kei Mori
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Patent number: 6107491Abstract: Diketopyrrolopyrroles of formula I ##STR1## wherein R.sub.1 is a radical of formula II--Y--X--Z--Q (II),whereinY is --CR.sub.3 R.sub.4, --SO.sub.2 --, --CO--, --Si(Hal).sub.2 --, --POHal--, wherein R.sub.3 and R.sub.4 are each independently of the other hydrogen or C.sub.1 -C.sub.4 alkyl, and Hal is halogen,X is an unsubstituted or substituted carbocylic or heterocyclic arylene group,Z is a single bond, uninterrupted linear or branched C.sub.1 -C.sub.30 alkylene, or linear or branched C.sub.2 -C.sub.30 alkylene which is interrupted once or more than once by a hetero atom, --CH.dbd.CH--,--C.tbd.C--, --N.dbd.CH--, --CH.dbd.N-- or --NH--, or is C.sub.5 -C.sub.12 cycloalkylene,Q is a polyreactive functional group, andR.sub.2 is C.sub.1 -C.sub.6 alkyl, ##STR2## or R.sub.1, and R.sub.7 is hydrogen or C.sub.1 -C.sub.Type: GrantFiled: January 26, 1999Date of Patent: August 22, 2000Assignee: Ciba Specialty Chemicals CorporationInventor: Sameer Eldin
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Patent number: 5919944Abstract: Diketopyrrolopyrroles of formula I ##STR1## wherein R.sub.1 is a radical of formula II--Y--X--Z--Q (II),whereinY is --CR.sub.3 R.sub.4, --SO.sub.2 --, --CO--, --Si(Hal).sub.2 --, --POHal--, wherein R.sub.3 and R.sub.4 are each independently of the other hydrogen or C.sub.1 -C.sub.4 alkyl, and Hal is halogen,X is an unsubstituted or substituted carbocylic or heterocyclic arylene group, Z is a single bond, uninterrupted linear or branched C.sub.1 -C.sub.30 alkylene, or linear or branched C.sub.2 -C.sub.30 alkylene which is interrupted once or more than once by a hetero atom, --CH.dbd.CH--, --C.tbd.C--, --N.dbd.CH--, --CH.dbd.N-- or --NH--, or is C.sub.5 -C.sub.12 cycloalkylene,Q is a polyreactive functional group, andR.sub.2 is C.sub.1 -C.sub.6 alkyl, ##STR2## or R.sub.1, and R.sub.7 is hydrogen or C.sub.1 -C.sub.Type: GrantFiled: July 20, 1998Date of Patent: July 6, 1999Assignee: Ciba Specialty Chemicals CorporationInventor: Sameer Eldin
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Patent number: 5866295Abstract: The present invention relates to novel photosensitive quinolone compounds, specifically novel 3-diazo 2,4-quinolinedione compounds, that may be used in a variety of applications, such as, photosensitive coating compositions, pharmaceuticals, agricultural, amongst others. The invention further relates to a process for making the novel photosensitive 3-diazo 2,4-quinolinedione compounds. These compounds are particularity useful as a photoactive component in a positive working photoresist composition, particularity for use as a deep ultraviolet (UV) photoresist.Type: GrantFiled: March 7, 1997Date of Patent: February 2, 1999Assignee: Clariant Finance (BVI) LimitedInventors: Joseph E. Oberlander, Dana L. Durham, Dinesh N. Khanna
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Patent number: 5821373Abstract: Solid solutions consisting of 3,6-bis(biphenyl-4-yl)- 2,5-dihydropyrrolo?3,4-c!pyrrole-1,4-dione and either a) a second 1,4-diketopyrrolopyrrole or b) a quinacridone, which are further defined herein, are outstandingly suited to pigmenting high molecular weight organic material.Type: GrantFiled: September 12, 1996Date of Patent: October 13, 1998Assignee: Ciba Specialty Chemicals CorporationInventors: Zhimin Hao, Olof Wallquist
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Patent number: 5811529Abstract: A fiber reactive dye having the formula ##STR1## wherein R.sub.1 and R.sub.3 are independently selected from the group consisting of; hydrogen; an alkyl group having from one to four carbon atoms; the foregoing alkyl group further substituted with one or more groups selected from hydroxy; amino; sulfo; halogen; an aryl radical; a heterocyclic radical or combination thereof; where for R.sub.3 said amino group maybe further substituted by a nitrogen heterocyclic fiber reactive group of the series: 1, 3, 5 mono or dichloro triazinyl; 1, 3, 5 mono or difluoro triazinyl; trichloropyrimidinyl; difluoropyrimidinyl; or monochlorodifluoro pyrimidinyl; where the nitrogen heterocycle may be further substituted by an: alkyl; or aryl amino group;wherein B is selected from the group consisting of a C.sub.2 to C.sub.4 alkyl chain; a substituted aryl or a heterocyclic radical;wherein X is selected from the group consisting of SO.sub.3 H; SO.sub.3 Na or a hydroxy group; and wherein Q.sub.1 and Q.sub.Type: GrantFiled: March 7, 1997Date of Patent: September 22, 1998Assignee: Dystar, L.P.Inventors: Danette R. Vines, Ronald P. Pedemonte
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Patent number: 5756689Abstract: The invention relates to a method of increasing the sensitivity of laser induced thermal imaging by using certain diazo compounds. The diazo compounds contain functional groups adjacent the diazo substituent capable of stabilizing these compounds. The invention is useful in the field of thermal transfer imaging for the production of various graphic arts media.Type: GrantFiled: May 19, 1997Date of Patent: May 26, 1998Assignee: Minnesota Mining and Manufacturing CompanyInventors: Stanley C. Busman, Gregory D. Cuny, Krzysztof A. Zaklika, Richard J. Ellis
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Patent number: 5688627Abstract: A water soluble diazonium salt composition made by the condensation of diazoaryl amines and aldehydes and precipitated to form a polymeric anionic species having both ZnCl.sub.4.sup.= and HSO.sub.4.sup.- moieties. These composition are blended with suitable binders, colorants and other optional components to produce light sensitive coating compositions. When applied to aluminum substrates, these light sensitive coating compositions form lithographic printing plates that are especially stable under high humidity conditions. Such plates may be developed by either water alone or by water which contains surfactants and/or a small amount of an organic solvent.Type: GrantFiled: July 2, 1996Date of Patent: November 18, 1997Assignee: Precision Lithograining Corp.Inventor: Albert S. Deutsch
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Patent number: 5534623Abstract: Polyunsaturated diazonium compounds suitable for use in negative working radiation sensitive compositions are provided. They may be produced by reacting an aromatic diazonium compound of the formula(A.sup.- N.sub.2.sup.+).sub.p --Ar--(R).sub.q --(XH).sub.rwith a polyethylenically unsaturated monoisocyanate compound of the general formula ##STR1## where p and q are integers ranging from 1 to 5, r is an integer ranging from 1 to 10; Ar represents a substituted or unsubstituted divalent or polyvalent radical derived from an aromatic or heteroaromatic compound; X represents O, S or a secondary or tertiary amino group; R represents a single bond or a substituted or unsubstituted divalent or other polyvalent radical and may be the same or different when q is greater than 1; A.sup.- represents an anion; Z represents the residue of a polyisocyanate OCN--Z--(NCO).sub.Type: GrantFiled: May 30, 1995Date of Patent: July 9, 1996Assignee: Du Pont (UK) LimitedInventors: John R. Wade, Michael J. Pratt, Jianrong Ren
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Patent number: 5466789Abstract: Polyunsaturated diazonium compounds suitable for use in negative working radiation sensitive compositions are provided. They may be produced by reacting an aromatic diazonium compound of the formula(A.sup.- N.sub.2.sup.+)p--Ar--(R)q--(XH)rwith a polyethlenically unsaturated monoisocyanate compound of the general formula ##STR1## where p and q are integers ranging from 1 to 5, r is an integer ranging from 1 to 10; Ar represents a substituted or unsubstituted divaient or polyvalent radical derived from an aromatic or heteroaromatic compound; X represents O, S or a secondary or tertiary amino group; R represents a single bond or a substituted or unsubstituted divalent or other polyvalent radical and may be the same or different when q is greater than 1; A.sup.- represents an anion; Z represents the residue of a polyisocyanate OCN--Z--(NCO)n where n is 1 or 2; and Y is the residue of a monohydroxy compound of the formula YOH where Y contains at least two ethylenically unsaturated double bonds.Type: GrantFiled: January 21, 1993Date of Patent: November 14, 1995Assignee: Du Pont (UK) LimitedInventors: John R. Wade, Michael J. Pratt, Jianrong Ren
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Patent number: 5459247Abstract: Bisazo compounds useful as charge generating materials having formula (I) are disclosed: ##STR1## wherein R represents hydrogen, an alkyl group having 1 to 4 carbon atoms, an alkoxyl group having 1 to 4 carbon atoms or a nitro group.Type: GrantFiled: February 25, 1994Date of Patent: October 17, 1995Assignee: Ricoh Company, Ltd.Inventor: Mitsuru Hashimoto
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Patent number: 5430130Abstract: An photosensitive polyfunctional aromatic diazo compound having at least two groups of Formula (uD) in the molecule, and a photosensitive composition using the same. The diazo compound can be handled under visible light free from ultraviolet, is highly photosensitive, has good shelf life, and is adequate as a photosensitive agent for lithographic printing plates and screen printing plates: ##STR1## wherein G.sup.1 is a substituent derived from alcoholic hydroxyl group; R.sup.1 and R.sup.2 are hydrogen, or alkyl or alkyloxy of 1 to 8 carbon atoms;R.sup.3 is alkyl or substituted alkyl of 1 to 8 carbon atoms, aralkyl or substituted aralkyl of 7 to 14 carbon atoms, or --CH.sub.2 CHG.sup.2 --CH.sub.2 --;X.sup.- is an anion based on protonic acid from which a proton is removed.Type: GrantFiled: July 21, 1993Date of Patent: July 4, 1995Assignee: Toyo Gosei Kogyo Co., Ltd.Inventors: Hirotada Iida, Noriaki Tochizawa, Yasuo Kuniyoshi, Masaharu Watanabe, Katsuyo Tokuda, Ichiro Hozumi
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Patent number: 5317093Abstract: Bisazo compounds, useful as organic photoconductive materials, having formula (I) or (II) are disclosed: ##STR1## wherein R represents hydrogen, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms or a nitro group; ##STR2## wherein A and B independently represent hydrogen or chloride provided that either A or B represents chloride.Type: GrantFiled: September 19, 1991Date of Patent: May 31, 1994Assignee: Ricoh Company, Ltd.Inventor: Mitsuru Hashimoto
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Patent number: 5312906Abstract: Bisazo compounds of formula (I), an intermediate for producing the bisazo compound of formula (I), and trisazo compounds of formula (II) for use in optical information recording media, and methods of producing these compounds are disclosed: ##STR1## wherein R represents hydrogen, an alkyl group having 1 to 20 carbon atoms; an aryl group selected from the group consisting of phenyl group, naphthyl group, mesityl group, and tri-t-butyl phenyl group; an alkoxyl group having 1 to 4 carbon atoms; a nitro group; a cyano group; chlorine; or bromine; n is an integer of 1, 2, or 3; and C.sub.p represents a coupler residue.Type: GrantFiled: July 24, 1992Date of Patent: May 17, 1994Assignee: Ricoh Company, Ltd.Inventor: Masakatsu Shimoda
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Patent number: 5310618Abstract: A light-sensitive composition comprising either an alkali-soluble resin or radical-polymerizable, unsaturated compound, and a diazonium compound represented by general formula (I) or (II):(S).sub.1 --(L.sup.1).sub.m --(D).sub.n (I)--(L.sup.2 (S)).sub.o --(L.sup.3 (D)).sub.P -- (II)wherein D is a diazonium salt group, S is a light absorbing group, L.sup.1, L.sup.2 and L.sup.3 are connecting groups connecting S and D, provided that S and D are not conjugated by L.sup.1, L.sup.2 and L.sup.3 ; l, m, n, o and p are integers.Type: GrantFiled: May 24, 1991Date of Patent: May 10, 1994Assignee: Fuji Photo Film Co., Ltd.Inventor: Kouichi Kawamura
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Patent number: 5308735Abstract: Disclosed is a photosensitive diazo resin for lithographic printing represented by the formula: ##STR1## wherein X.sup.- is a counter anion, Y is a divalent bonding group selected from the group consisting of --NH--, --S-- and --O--, R.sub.1, R.sub.2 and R.sub.3 are groups which are independently selected from the group consisting of hydrogen, an alkyl group and an alkoxy group, R.sub.4 and R.sub.5 are groups which are independently selected from the group consisting of hydrogen, an alkyl group and a phenyl group, 1 and m are integers which satisfy the relation:1+m=2 to 100, 1/m=30 to 99/1 to 70and A is a quaternary ammonium salt-containing group represented by the formula: ##STR2## (wherein B is a straight or branched divalent C.sub.1-10 alkyl group which bonds to an aromatic ring by a group selected from the group consisting of --CH.sub.2 --, --CO--, --O--, --S-- and --N--, and R.sub.6, R.sub.7 and R.sub.8 are groups which are independently selected from the group consisting of hydrogen and a C.sub.Type: GrantFiled: October 29, 1992Date of Patent: May 3, 1994Assignee: Nippon Paint Co., Ltd.Inventors: Kazunori Kanda, Edward Lam, Osamu Nanba
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Patent number: 5262526Abstract: A fluorescent compound, which is readily capable of forming a stable complex with a rare-earth metal ion having fluorescence with satisfactory intensity even in an aqueous system and long fluorescence lifetime when formed a complex with the rare-earth metal ion, a complex of the fluorescent compound and the rare-earth metal ion, and a labelled reagent made therefrom, together with a specific binding assay using said labelling agent.A fluorescent compound expressed by the following formula A, typically exemplified by 2,15-diaza[3,3](2,9)-1,10-phenanthrolinophane-N.sup.2,N.sup.15 -diacetic acid.Type: GrantFiled: December 20, 1991Date of Patent: November 16, 1993Assignees: Dojindo Laboratories, Mochida Pharmaceutical Co., Ltd.Inventors: Kazumi Sasamoto, Daikichi Horiguchi, Masahiro Nobuhara, Hiroshi Mochizuki
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Patent number: 5256517Abstract: A positive-working radiation-sensitive mixture is described which essentially contains a photoactive component and a water-insoluble binder which is soluble, or at least swellable, in aqueous alkaline solution, wherein a compound is used, as photoactive component, which contains .alpha.-diazo-.beta.-keto ester units and sulfonate units of the formula I ##STR1## in which R.sup.1 and R.sup.2, independently of one another, are an unsubstituted or substituted aliphatic, cycloaliphatic, araliphatic or aromatic radical having 4 to 20 carbon atoms, it being possible for individual CH.sub.2 groups to be replaced by oxygen or sulfur atoms or by N or NH groups and/or contain keto groups,X is an unsubstituted or substituted aliphatic, cycloaliphatic, carbocyclic, heterocyclic or araliphatic radical having 2 to 22 carbon atoms, it being possible for individual CH.sub.2 groups to be replaced by oxygen or sulfur atoms or by the groups --NR.sup.3 --, --C(O)--0--, --C(O)--NR.sup.3 --, ##STR2## --NR.sup.3 --C(O)--NR.sup.Type: GrantFiled: May 1, 1991Date of Patent: October 26, 1993Assignee: Hoechst AktiengesellschaftInventors: Horst Roeschert, Georg Pawlowski, Hans-Joachim Merrem, Ralph Dammel, Walter Spiess
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Patent number: 5206349Abstract: An aromatic diazo compound having at least two groups of Formula (I) in the molecule.This aromatic diazo compound can be handled under visible light free from ultraviolet, is high in photosensitivity, and can be produced by a simple synthesis method.The diazo compound has a high solubility in organic solvents, appropriate for use as a photosensitive material for a lithographic printing plate, can be easily developed by an alkaline developing solution mainly based on an alkaline aqueous solution, and has a water solubility appropriate for use in a screen printing plate. ##STR1## wherein Z.sup.1 indicates ##STR2## wherein .phi..sup.1 is arylene or substituted arylene; and -.phi..sup.2 is >C.dbd.O, lower alkyl, lower alkylene, or aryl or substituted aryl.R.sup.1 and R.sup.2 are H, alkyl of C.sub.1 to C.sub.8, or alkyloxy of C.sub.1 to C.sub.8 ; X.sup.- is anion; and R.sup.Type: GrantFiled: August 5, 1991Date of Patent: April 27, 1993Assignee: Toyo Gosei Kogy Co., Ltd.Inventors: Hirotada Iida, Hajime Arai, Hitoshi Sugiura, Katsuhiko Sugou, Kieko Harada
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Patent number: 5200291Abstract: A polymeric compound having the formula ##STR1## wherein x ranges from about 0.05 to about 0.5y ranges from about 0.80 to about 0.35z ranges from about 0.10 to about 0.25n ranges from about 50 to about 1500R is selected from the group consisting of phenyl and C.sub.1 to C.sub.4 alkyl substituted phenyl;K is selected from the group consisting of ##STR2## --S--, --O--, and --CH.sub.2 --, or is absent; P and P.sub.1 are selected from the group consisting of C.sub.1 to C.sub.4 alkyl, methoxy, ethoxy, butoxy, and H; andP.sub.1 may be the same as P or different.Type: GrantFiled: April 11, 1991Date of Patent: April 6, 1993Assignee: Hoechst Celanese CorporationInventor: Stanley F. Wanat
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Patent number: 5191069Abstract: Polyfunctional compounds containing .alpha.-diazo-.beta.-keto ester units and sulfonate units are disclosed. The polyfunctional compounds have high sensitivity in the deep UV and high thermal stability. Processes for producing the compounds are disclosed. A preferred process first synthesizes .beta.-ketoester/sulfonate precursors and then uses diazo transfer to convert the precursors into the novel compounds. Radiation-sensitive mixtures containing the compounds are also disclosed.Type: GrantFiled: May 1, 1991Date of Patent: March 2, 1993Assignee: Hoechst AktiengesellschaftInventors: Horst Roeschert, Georg Pawlowski, Hans-Joachim Merrem, Ralph Dammel
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Patent number: 5175258Abstract: A process for the preparation of photogenerating pigments which comprises the reaction of a diaminofluorenone with an alkali nitrite, an acid, and a tetrafluoroborate; thereafter reacting the resulting product with an anilide coupler; and subsequently annealing the product obtained.Type: GrantFiled: December 14, 1990Date of Patent: December 29, 1992Assignee: Xerox CorporationInventors: Kock-Yee Law, Ihor W. Tarnawskyj
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Patent number: 5145997Abstract: Poly (alkylene oxide) substituted acetoacetanilides of the formula: ##STR1## wherein B comprises a divalent bridging moiety selected from the group consisting of C.sub.1 -C.sub.6 alkylene, --NHSO.sub.2 --, --O--, --CO--, --COO--, and --NCHO--; X comprises a poly (alkylene oxide) having a number average molecular weight of about 200 to 10,000; R comprises 0 to 4 moieties independently selected from the group consisting of C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy and halogen; and d is an integer of 1 to 3. The poly (alkylene oxide) substituted acetoacetanilides are prepared by reacting a poly (alkylene oxide) monoamine, diamine or triamine with isatoic anhydride followed by acetoacetylation of the resultant aminobenzamide. The substituted acetoacetanilides are useful for preparing improved diarylide pigment compositions which in turn are useful for preparing storage stable printing inks (especially of the publication gravure type).Type: GrantFiled: February 12, 1991Date of Patent: September 8, 1992Assignee: Sun Chemical CorporationInventors: Russell J. Schwartz, Anthony C. Zwirgzdas, Terence R. Chamberlain
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Patent number: 5097022Abstract: An electrophotographic photoconductor comprises an electroconductive support and a photoconductive layer formed thereon comprising a bisazo compound having the formula (I) serving as a charge generating material: ##STR1## wherein Y represents a halogen, an alkyl group which may have a substituent, an alkoxyl group, an acyl group, a substituted amino group, a cyano group or a nitro group; R represents hydrogen, or an alkyl group which may have a substitutent; and Ar represents an aryl group which may have a substituent.Type: GrantFiled: November 3, 1989Date of Patent: March 17, 1992Assignee: Ricoh Company, Ltd.Inventors: Masaomi Sasaki, Tomoyuki Shimada, Mitsuru Hashimoto
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Patent number: 5081233Abstract: A bisazo compound of the general formula: ##STR1## where Ar is selected from the group consisting of substituents (a) .about. (i), a dinitro compound, a diamino compound, and a tetrazonium salt, which respectively serve as a starting material, a first intermediate and a second intermediate for producing the above bisazo compound are prepared, and an electrophotographic photoconductor comprising an electroconductive support having thereon a photoconductive layer containing any of the above bisazo compounds is disclosed.Type: GrantFiled: October 24, 1988Date of Patent: January 14, 1992Assignee: Ricoh Company, Ltd.Inventors: Masaomi Sasaki, Tomoyuki Shimada
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Patent number: 5075427Abstract: The present invention is directed to aqueous compositions of organic diazo compounds which are capable of being readily handled in commercial applications and to the surface modification of polymeric substrates utilizing the subject diazo composition.Type: GrantFiled: November 19, 1990Date of Patent: December 24, 1991Assignee: W. R. Grace & Co.-Conn.Inventors: Uan G. Kang, Joseph W. Raksis, Clifton L. Kehr, Clifford A. Ferrin, Jr.
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Patent number: 5062894Abstract: Diarylide pigment compositions useful for preparing storage stable printing inks (especially of the publication gravure type) are prepared using a poly (alkylene oxide) substituted acetoacetanilide together with a typical acetoacetanilide and coupling the mixture of acetoacetanilides with tetrazotized dichlorobenzidine.Type: GrantFiled: June 25, 1991Date of Patent: November 5, 1991Assignee: Sun Chemical CorporationInventors: Russell J. Schwartz, Anthony C. Zwirgzdas, Terence R. Chamberlain
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Patent number: 5055367Abstract: Disclosed is an imaging member which comprises a conductive substrate and a photogenerating layer containing a compound selected from the group consisting of: ##STR1## and mixtures thereof, wherein Cp represents a coupler group.Type: GrantFiled: May 31, 1990Date of Patent: October 8, 1991Assignee: Xerox CorporationInventor: Kock-Yee Law
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Patent number: 4996301Abstract: Polyfunctional .alpha.-diazo-.beta.-keto esters of the general formula I are described ##STR1## in which R.sup.1 denotes an aliphatic, cycloaliphatic or araliphatic or aromatic radical having 4 to 20 carbon atoms, in which individual CH.sub.2 groups can be replaced by oxygen or sulfur atoms or by N-- or NH groups and/or contain keto groups,X denotes an aliphatic, cycloaliphatic, carbocyclic, heterocyclic or araliphatic radical having 2 to 22 carbon atoms, in which individual CH.sub.2 groups can be replaced by oxygen or sulfur atoms or by the groups ##STR2## in which R.sup.2 and R.sup.3 independently of one another represent hydrogen or an aliphatic, carbocyclic or araliphatic radical,m denotes an integer from 2 to 10 andn denotes an integer from 0 to 2,whereinm-n is .gtoreq.2.The compounds mentioned are used as photoactive components in radiation-sensitive mixtures.Type: GrantFiled: January 12, 1990Date of Patent: February 26, 1991Assignee: Hoechst AktiengesellschaftInventors: Peter Wilharm, Hans-Joachim Merrem, Georg Pawlowski
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Patent number: 4987221Abstract: Bisdiazonium salts of the formula (1) ##STR1## in which R denotes a linear or branched alkyl or alkoxyalkyl radical having 3-5 carbon atoms and X.sup.- represents the radical of a strong acid or of a zinc chloride double salt, and a process for their preparation by diazotizing a 4,4'-diamino-3,3'-dialkoxybiphenyl of the formula (2) ##STR2## in which R has the meaning mentioned, in an aqueous, strong, non-oxidizing inorganic or organic acid at temperatures from about -10.degree. C. to about +40.degree. C. by means of an alkali metal nitrite, and precipitating the resulting bisdiazonium salts by adding an alkali metal chloride, bisulfate, monosulfonate of 1,5-naphthalenedisulfonic acid or tetrafluoroborate or zinc chloride.These salts are useful in dyeing and printing textile fiber materials by the methods of the ice color technique, using suitable coupling components; they are also useful for preparing photographic tracings by the methods of reprography.Type: GrantFiled: March 27, 1986Date of Patent: January 22, 1991Assignee: Hoechst AktiengesellschaftInventors: Hasso Hertel, Klaus Hunger, Heinrich Frolich
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Patent number: 4987258Abstract: The invention relates to 4,4'-diaminodiphenyl compounds of the formula I ##STR1## in which X denotes the n-propyl, isopropyl, n-butyl, isobutyl, 1-methylpropyl, n-propoxy, isopropoxy, isobutoxy, 1-methylpropoxy or 2-methoxyethoxy radical and A is 0 or the equivalent of an inorganic acid.The preparation is effected by reducing ortho-X-substituted nitrobenzene and benzidine rearrangement of the resulting hydrazobenzene derivative. The compounds of the formula (I) are suitable for use as components in the preparation of dyes and pigments.Type: GrantFiled: February 20, 1987Date of Patent: January 22, 1991Assignee: Hoechst AktiengesellschaftInventors: Klaus Hunger, Heinrich Frolich, Kurt C. Habig
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Patent number: 4973672Abstract: Coloring natural or synthetic fiber material containing hydroxyls or nitrogen is achieved by printing or dyeing the fiber material with a water-soluble disazo dyestuff of the formula ##STR1## wherein R.sup.1 is alkyl, alkoxy or alkoxyethoxy, each having 3-6 carbon atoms, B.sup.1 is the radical of a 1-amino-8-hydroxynaphthalene monosulphonic or disulphonic acid and B.sup.2 is the same as B.sup.1 or another napthyl moiety.Type: GrantFiled: March 27, 1989Date of Patent: November 27, 1990Assignee: Cassella AktiengesellschaftInventors: Wolfgang Bauer, Klaus Hunger
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Patent number: 4946508Abstract: Disazo pyrazolone pigments are provided which have improved properties achieved by incorporating certain azomethine compounds. The pigment is prepared by reacting a primary amine terminated alkylene oxide polymer and acetoacetanilide or substituted acetoacetanilide to form an azomethine coupler, and subsequently co-reacting the azomethine coupler and a pyrazolone coupler with tetrazotized 3,3'-dichlorobenzidine or tetrazotized o-dianisidine. The pigment is useful in printing ink, plastics and paints.Type: GrantFiled: May 23, 1989Date of Patent: August 7, 1990Assignee: Sun Chemical CorporationInventors: Russell J. Schwartz, Manuel Z. Gregorio
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Patent number: 4946509Abstract: Diarylide pigments modified with alkylene oxide polymers. The modified pigments are useful in both water-based and solvent-based coating and ink compositions.Type: GrantFiled: May 23, 1989Date of Patent: August 7, 1990Assignee: Sun Chemical CorporationInventors: Russell J. Schwartz, Manuel Z. Gregorio, Anthony C. Zwirgzdas
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Patent number: 4914000Abstract: A light-sensitive compound having the formula: ##STR1## wherein R.sub.3 is selected from the group consisting of phenyl and C.sub.1 to C.sub.4 alklyl substituted phenyl.--K-- is selected from the group consisting of ##STR2## --S--, --O--, and --CH.sub.2 --, or is absent; R.sub.1 and R.sub.2 are independently selected from the group consisting of C.sub.1 to C.sub.4 alkyl, methoxy, ethoxy, butoxy, and H;X-- is an anion; andR denotes a hydrogen atom or a C.sub.1 to C.sub.4 alkyl group.Type: GrantFiled: February 3, 1988Date of Patent: April 3, 1990Assignee: Hoechst Celanese CorporationInventor: Major S. Dhillon
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Patent number: 4902601Abstract: Radiation sensitive material suitable for the production of radiation sensitive plates for lithographic printing plate manufacture is based on a polymer including a plurality of structural units represented by the formula: ##STR1## in which, R represents H or CH.sub.3 ; each R.sub.1, which may be the same or different represents H or alkyl; R.sub.2 represents a single bond or a substituted or unsubstituted divalent radical; Ar represents a substituted or unsubstituted divalent radical derived from an aromatic or heteroaromatic compound; X represents O, S or NH; A represents an anion; Y represents a carbonyl oxy or aromatic radical; and n is an integer equal to or greater than 1.Type: GrantFiled: January 19, 1989Date of Patent: February 20, 1990Assignee: Vickers PLCInventors: Rodney M. Potts, Michael J. Pratt, Keith M. Fletcher
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Patent number: 4889924Abstract: A bisazo compound having good electrophotographic properties is disclosed, which is represented by formula (I) ##STR1## wherein X represents a hydrogen atom, a chlorine atom or a nitro group. A process for producing the bisazo compound is also disclosed.Type: GrantFiled: October 2, 1987Date of Patent: December 26, 1989Assignee: Fuji Xerox Co., Ltd.Inventors: Yutaka Akasaki, Akihiko Tokita, Kaoru Torikoshi, Akira Imai, Touru Ishii