Specified Rate-affecting Material Is An Amide Or Tertiary Amine Patents (Class 522/14)
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Patent number: 5378579Abstract: A photopolymerizable composition comprising(A) an addition-polymerizable compound having an ethylenically unsaturated double bond,(B) a compound of the formula: ##STR1## [wherein R.sup.1 is a substituted or nonsubstituted phenyl group, R.sup.2 and R.sup.3 are the same or different and indicate a hydrogen atom or a C.sub.1-4 alkyl group, R.sup.4 in an alkylene group which may have at least one substituent selected from alkyl, hydroxyl and oxo (.dbd.O) on a main chain, or which may contain at least one member selected from an oxygen atom and a cycloalkylene group in a main chain, R.sup.5 is a hydrogen atom or a methyl group, and a and b are independently 0 or 1],(C) a light absorbing compound, and(D) a film-forming polymer having alkaline solubility or alkaline swelling characteristic is disclosed. There is also disclosed a photosensitive lithographic printing plate comprising the photopolymerizable composition.Type: GrantFiled: July 8, 1992Date of Patent: January 3, 1995Assignee: Nippon Paint Co., Ltd.Inventors: Seiji Arimatsu, Takakazu Hase, Yoshifumi Ichinose
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Patent number: 5376691Abstract: The invention describes a material for making temporary crowns and bridges that comprises two pastes and can be mixed in a static mixer/application in one cycle without the incorporation of bubbles, and can be easily pressed out. The polymers produced from this are aesthetically pleasing and remarkably break-resistant. Their polymerization-related shrinkage proves to be extremely low. Their radiopaqueness meets clinical requirements.Type: GrantFiled: March 1, 1993Date of Patent: December 27, 1994Assignee: Ernst Muhlbaner KGInventors: Ulrich May, Jurgen Engelbrecht, Ernst Muhlbauer, Edgar Lein
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Patent number: 5362769Abstract: The present invention is directed to orthodontic adhesive formulations, both light curable in the visible wavelength range, and self-curing, for use in the adherence of orthodontic appliances to the surface of etched human teeth. These formulations exhibit a high degree of surface wetting, an available source of leachable fluoride, low polymerization shrinkage, high physical properties and adhesion, and in the light curable embodiment, a post-curing capability.Type: GrantFiled: May 7, 1992Date of Patent: November 8, 1994Assignees: Ormco Corporation, Kerr Manufacturing Co.Inventors: Duncan E. Waller, Raymond F. Wong
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Patent number: 5358976Abstract: Curable norbornene-thiol compositions are stabilized by addition of a non-acidic Nitroso compound.Type: GrantFiled: December 23, 1992Date of Patent: October 25, 1994Assignee: Loctite (Ireland) LimitedInventors: Joseph P. Dowling, Sarah C. Richardson, Killian Quigley
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Patent number: 5326792Abstract: A photosensitive cover coating agent forming an insulating, protective coating having superior compatibility, sensitivity, heat resistance, adhesion, electrical properties and flexibility is provided,which coating agent is obtained by mixing a polymer (A) of repetition units of the formula ##STR1## wherein R.sup.1 is ##STR2## R.sup.2 is a divalent organic group, a compound (B) containing two or more (meth)acryloyl groups in one molecule,a compound (C) of the formula ##STR3## wherein Z is a divalent aliphatic or alicyclic group, R.sup.3 is H, monovalent organic group or characteristic group and R.sup.4 is H or --Z--R.sup.3, in 0.01 to 0.80 mol equivalent based on compound (B), the total quantity of (B) and (C) being 20 to 200 wt. parts per 100 wt. parts of (A), anda photopolymerization initiator or a sensitizing agent (D), in 0.5 to 20 wt. parts per 100 wt. parts of (A).Type: GrantFiled: November 23, 1992Date of Patent: July 5, 1994Assignee: Chisso CorporationInventors: Yoshinori Masaki, Kouichi Kunimune, Hirotoshi Maeda
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Patent number: 5321053Abstract: A dental composition comprising a vinyl monomer containing at least one acidic group in the molecule thereof and an initiator capable of photopolymerizing said monomer by visible light, characterized in that said initiator consisting essentially of:(a) a photosensitizer selected from an .alpha.-diketone, a quinone and a derivative thereof, and,(b) an accelerator selected from a compound containing at least one mercapto group in the molecule thereof is provided by the present invention.Type: GrantFiled: February 6, 1990Date of Patent: June 14, 1994Assignee: Kuraray Co., Ltd.Inventors: Kenichi Hino, Junichi Yamauchi, Koji Nishida
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Patent number: 5268255Abstract: A printed circuit board has a resist layer made from a photo-setting resist composition containing:(A) a polyfunctional unsaturated compound which is solid at room temperature,(B) a polyfunctional unsaturated compound which is liquid at room temperature,(C) a photopolymerization initiator,(D) an epoxy resin,(E) at least one member selected from the group consisting of:(i) a curing agent for the epoxy resin and either melamine or the derivative thereof, and(ii) a compound having a 2,4-diamino-s-triazine ring and an imidazole ring in the molecule.Type: GrantFiled: September 30, 1991Date of Patent: December 7, 1993Assignee: Hitachi, Ltd.Inventors: Hiroshi Kikuchi, Makio Watanabe, Shinichiro Imabayashi, Reiko Yano, Isamu Tanaka, Hitoshi Oka, Yukihiro Taniguchi, Shigeru Fujita
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Patent number: 5254602Abstract: A photocurable compound prepared as a starting material by incorporation therein of a composition comprising a fluorescein compound photoreducing dye, tribenzylamine, and at least one specific peroxide permits production of a shaped article which, on exposure to visible light, exhibits high curability and acquires hardness virtually indiscriminately on the obverse and reverse sides of the article. A mixture comprising both or either of an unsaturated polyester resin and an epoxy acrylate resin which are photocurable compounds, glass fibers, and a specific peroxide, is convenient for the production of specific cured shaped articles particularly by the filament winding technique or the drawing technique.Type: GrantFiled: February 21, 1992Date of Patent: October 19, 1993Assignee: Nippon Oil & Fats Co., Ltd.Inventors: Yoshihiro Tomura, Shigeki Banno
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Patent number: 5248805Abstract: Radiation-sensitive, ethylenically unsaturated compounds and a process for their preparation. The ethylenically unsaturated organic compounds are of the general formula ##STR1## where R is alkyl, aryl or a radical R.sup.1 andR.sup.1 is a radical ##STR2## where R.sup.2 to R.sup.6 are each H, alkyl, OH, OAlkyl, SH, SAlkyl, halogen, N (Alkyl).sub.2 or N (Alkyl) (Aryl) and at least one but not more than three of the radicals R.sup.2 to R.sup.6 is or are a radical ##STR3## where X is alkylene, cycloalkylene, oxaalkylene or arylene, Y is H or CH.sub.3 -- and Z is O or NY.The novel radiation-sensitive ethylenically unsaturated compounds are suitable for the preparation of polymeric radiation-sensitive compounds.Type: GrantFiled: March 2, 1992Date of Patent: September 28, 1993Assignee: BASF AktiengesellschaftInventors: Andreas Boettcher, Gerd Rehmer
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Patent number: 5236967Abstract: An optical molding composition is used for casting and does not cause irritation to the skin or possess a bad smell. This composition comprises1. an actinic radiation-curable, radical-polymerizable organic compound comprising(1) one or more polythiol compounds and(2) one or more polyene compounds each having at least two actinic radiation-reactive carbon-to-carbon double bonds in the molecule, and2. an actinic radiation-sensitive radical polymerization initiator.Type: GrantFiled: February 18, 1992Date of Patent: August 17, 1993Assignee: Asahi Denka Kogyo K.K.Inventors: Kazuo Ohkawa, Seiichi Saito
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Patent number: 5236808Abstract: Photopolymerizable compositions containing photoinitiator systems that absorb in the visible are disclosed. The photoinitiator system comprises a sensitizer which is a compound of the structure I: ##STR1## wherein R.sub.2 and R.sub.Type: GrantFiled: April 13, 1992Date of Patent: August 17, 1993Assignee: E. I. Du Pont de Nemours and CompanyInventor: William K. Smothers
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Patent number: 5235015Abstract: Novel photosensitive compositions based on azlactone derived polymers are described. The polymers have a hydrocarbyl backbone and pendant peptide groups with free-radically polymerizable functionality attached thereto, said polymer further comprising at least one oxyacid group or salt thereof, and optionally quaternary ammonium salt groups. A high speed durable printing plate having a mild pH aqueous developability is disclosed which incorporates these polymers in combination with a photoinitiator. The polymers are also useful as proofing films in graphic arts applications.Type: GrantFiled: February 21, 1991Date of Patent: August 10, 1993Assignee: Minnesota Mining and Manufacturing CompanyInventors: M. Zaki Ali, Mahfuza B. Ali, Dean M. Moren
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Patent number: 5212046Abstract: A photoacid-generating photoresist composition sensitized with an aromatic, multi-ring, heterocylcic nitrogen containing sensitizer, preferably a ring extended phenothiazine derivative. The use of the sensitizer permits exposure of photoresists to near UV irradiation where such photoresists have heretofore been exposed to deep UV irradiation. The invention is especially useful for acid hardening photoresist systems.Type: GrantFiled: June 28, 1991Date of Patent: May 18, 1993Assignee: Shipley Company Inc.Inventors: Angelo A. Lamola, Gary Calabrese, Roger Sinta
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Patent number: 5212271Abstract: A process for texturing a coating via exposing a photocurable composition comprising a multifunctional urea compound, an ethylenically unsaturated compound, and an aromatic ketone photosensitizer that functions through a hydrogen abstraction mechanism when exposed to ultraviolet light.Type: GrantFiled: December 22, 1989Date of Patent: May 18, 1993Assignee: Texaco Chemical CompanyInventors: Alison D. Beckett, Joseph V. Koleske, Richard M. Gerkin
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Patent number: 5210109Abstract: This invention provides hardenable compositions useful as construction media for a wide range of applications. Particular utility is found in the dental and medical arts where such compositions are highly suitable for the formation and construction of denture base, denture baseplates, denture liners, denture repair, custom trays, veneering for crowns and bridgework, artificial teeth, veneers and repair for natural teeth, and tooth restorative fillings. Such materials having improved impact strengths and elastic moduli when hardened are disclosed which include rubber-modified polymer.Type: GrantFiled: September 21, 1992Date of Patent: May 11, 1993Assignee: Dentsply Research & Development Corp.Inventors: Louis H. Tateosian, W. Donald Wilson
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Patent number: 5207577Abstract: A dental adhesive comprising a (meth)acryloylaminoalkyl carboxylate of the formula ##STR1## in which R.sup.1 represents hydrogen or methyl;R.sup.2 represents methylene or ethylene; andR.sup.3 represents hydrogen, methyl, or ethyl;and at least one of an initiator, a non-toxic solvent, and a filler. The dental adhesive is useful to effect a strong adhesive bonding of dental materials to collagen-containing materials.Type: GrantFiled: January 25, 1991Date of Patent: May 4, 1993Assignee: Bayer AktiengesellschaftInventors: Michael Muller, Wolfgang Podszun
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Patent number: 5202221Abstract: The present invention relates to a light-sensitive composition comprising (a) a photo-crosslinkable polymer having a maleimido group at a side chain and (b) a sensitizer such as the following compounds: ##STR1## The present invention provides a light-sensitive composition having very high sensitivity; providing excellent images during only a short exposure time; and being sensitive to light of long wave length.Type: GrantFiled: November 9, 1989Date of Patent: April 13, 1993Assignee: Fuji Photo Film Co., Ltd.Inventors: Masanori Imai, Noriaki Watanabe, Kouichi Kawamura
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Patent number: 5196457Abstract: Resin composition, that can be used for manufacturing a prepreg, comprising a liquid epoxy resin, a monomer reactive with the epoxy resin and a hardening catalyst for the epoxy resin, an unsaturated polyester, a monomer reactive with the unsaturated polyester and a hardening catalyst for the unsaturated polyester, whereby the catalyst for the unsaturated polyester is a first catalyst that has a working range below 40.degree. C. and the catalyst for the epoxy resin is a second catalyst that has a working range above 40.degree. C.Type: GrantFiled: June 28, 1990Date of Patent: March 23, 1993Assignee: DSM N.V.Inventors: Paul Wilkinson, Arno Montorfano
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Patent number: 5169879Abstract: Compositions which cure by UV radiation in less than one second are obtained by mixing an alkenyl containing polydiorganosiloxane, a mercapto functional crosslinker of the mercapto functional polyorganosiloxane or mercapto organic compounds, a photosensitizer, a viscosity stabilizer, and optionally a reinforcing agent. These compositions can be packaged in one container and can be used as the primary coating for optical fibers.Type: GrantFiled: April 19, 1990Date of Patent: December 8, 1992Assignee: Dow Corning CorporationInventors: Chi-long Lee, Michael A. Lutz
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Patent number: 5153236Abstract: A photopolymerizable composition comprising an addition polymerizable compound, an N-aryl-.alpha.-amino acid and a photosensitizer capable of absorbing a light having a wavelength of 300 nm or more such as thioxanthones, isoalloxazines, coumarines, and the like is excellent in sensitivity to irradiated light and is suitable for preparing relief images, photoresists, etc.Type: GrantFiled: June 13, 1991Date of Patent: October 6, 1992Assignee: Hitachi Chemical Co., Ltd.Inventors: Makoto Kaji, Futami Kaneko, Nobuyuki Hayashi
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Patent number: 5153100Abstract: Photopolymerizable compositions in which the photoinitiator system contains a hexaarylbisimidazole and/or a p-dialkyaminophenyl carbonyl compound in combination with a borate anion coinitiator are disclosed.Type: GrantFiled: August 27, 1990Date of Patent: October 6, 1992Assignee: E. I. du Pont de Nemours and CompanyInventors: Gregory C. Weed, Dietrich Fabricius
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Patent number: 5151453Abstract: Two-part dental cement systems based on glass ionomers which are curable on exposure to light. The dental cement systems comprise a two-part blend of sodium N(p-tolyl)glycine-glycidyl methacrylate (Na NTG-GMA) and pyromellitic dianhydride-methyl methacrylate (PMDM) resins and glass ionomers.Type: GrantFiled: August 1, 1990Date of Patent: September 29, 1992Assignee: Den-Mat CorporationInventors: Robert L. Ibsen, Donald R. Pacropis, William R. Glace
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Patent number: 5145884Abstract: An ultraviolet-hardenable adhesive for bonding a non-water swellable, ophthalmic-lens to a support member, in producing a non-water swellable ophthalmic lens, the adhesive containing at least one photopolymerizing monomer, and at least one photoinitiator, the at least one photopolymerizing monomer being selected from the group consisting of acrylates or methacrylates represented by following general formulas (I) and (II): ##STR1## wherein R.sub.1 is hydrogen or methyl,R.sub.2 is hydrogen or methyl,R.sub.3 is hydrogen or methyl,m is a positive integer from 2 to 20, andn is a positive integer from 1 to 5.A method of bonding a lens blank to a support member with an adhesive, and a processing of manufacturing a lens using an adhesive, are also disclosed.Type: GrantFiled: August 16, 1990Date of Patent: September 8, 1992Assignee: Menicon Co., Ltd.Inventors: Yasuyoshi Yamamoto, Yuzo Kaga, Toshiharu Yoshikawa, Akira Moribe
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Patent number: 5143947Abstract: Radiation curable compositions useful as coatings for wood, metal, glass, fabric, paper, fiber and plastics are made from copolymers of 4-hydroxystyrene and an alkadiene or an allyl ester of an ethylenically unsaturated acid blended wit ethylenically unsaturated compounds.Type: GrantFiled: November 13, 1989Date of Patent: September 1, 1992Assignee: Hoechst Celanese CorporationInventor: Balaram Gupta
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Patent number: 5141990Abstract: In-situ development of an ultraviolet absorber is provided by a compound such as a hydroxy-phenyl-triazole containing a group which protects the absorber during actinically activated polymerization by light at first frequency. After polymerization the protective group is removed by actinic reaction at a second frequency lower than the first frequency. The protective group is formed by replacing the hydrogen of the hydroxyl group with an acyl group containing 1 to 3 carbon atoms or an acryloxy group of the formula: ##STR1## where R.sup.1 is either an alkyl containing 1 to 6 carbon atoms or --CH.dbd.CH.sub.2.Type: GrantFiled: October 25, 1989Date of Patent: August 25, 1992Assignee: California Institute of TechnologyInventors: Vincent B. McKoy, Amitava Gupta
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Patent number: 5137800Abstract: A polymerizable composition and a method are disclosed. The composition includes a photopolymerizable monomer and a photoinitiator system for the monomer. The system, in one embodiment, is one wherein a ray of activating radiation which enters a body of the composition through a surface thereof activates the photoinitiator system and causes polymerization at each of a succession of points, the first such point being immediately adjacent the surface and subsequent points being successively farther from the surface in the direction of travel of the ray of activating radiation, the distance from the surface to the point of the succession farthest therefrom varying as a function of at least one of(a) the intensity of the activating radiation and(b) the time during which the activating radiation enters the body through the surface.Type: GrantFiled: June 14, 1990Date of Patent: August 11, 1992Assignee: StereoGraphics Limited PartnershipInventors: Douglas C. Neckers, Oscar Valdes-Aguilera, Krishan S. Raghuveer, Darrell G. Watson
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Patent number: 5112723Abstract: In a photosensitive recording element which contains at least one photopolymerizable recording layer (B) consisting ofb.sub.1) at least one partially of virtually completely hydrolyzed poly(vinyl alkanecarboxylate) and/or at least one partially or virtually completely hydrolyzed vinyl alkanecarboxylate/alkylene oxide graft copolymer as a binder,b.sub.2) at least one photopolymerization initiator,b.sub.3) at least one photopolymerizable olefinically unsaturated compound (monomer) which is compatible with the binder (b.sub.1), and/or photopolymerizable olefinically unsaturated radicals which are bonded as side radicals and/or terminal radicals to the binder (b.sub.1), andb.sub.4) at least two assistants, at least one of the said assistants (b.sub.4) has been selected from the group consisting ofb.sub.41) the isoalloxazines and the alloxazines, and at least one of the other assistants has been selected from the group consisting ofb.sub.Type: GrantFiled: February 8, 1990Date of Patent: May 12, 1992Assignee: BASF AktiengesellschaftInventors: Wolfgang Huemmer, Walter Dobler, Dieter Littmann
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Patent number: 5112721Abstract: Combinations of selected photosensitizers produce unexpected increases in the both the photospeed of, and the resolution obtainable from, photopolymerizable compositions. The combinations contain one photosensitizer, known as the sensitizer, and a second photosensitizer, known as the co-sensitizer. The co-sensitizer has an absorbance maximum at a longer wavelength than the sensitizer and is generally present a much lower concentration than the sensitizer.Type: GrantFiled: July 19, 1991Date of Patent: May 12, 1992Assignee: E. I. Du Pont de Nemours and CompanyInventor: August D. Kuchta
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Patent number: 5112880Abstract: A light-curable orthodontic bracket adhesive composition is provided for bonding an orthodontic bracket to the surface of a human tooth. The composition contains a particulate filler material, an acrylate-based resin, and a photoinitiator composition effective to catalyze polymerization upon irradiation. A method of using the composition is also provided.Type: GrantFiled: March 9, 1990Date of Patent: May 12, 1992Assignees: Gingi-Pak, Sankin Kogyo K.K. Industry Ltd.Inventors: Masayoshi Tsunekawa, Raymond L. Ramirez
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Patent number: 5102773Abstract: A photosensitive recording material contains a mixture of carboxyl-containing polymers having ethylenically unsaturated side groups, one or more ethylenically unsaturated monomeric compounds, a photoinitiator and a .beta.-aminoalcohol.It is suitable for the production of printing plates.Type: GrantFiled: October 20, 1989Date of Patent: April 7, 1992Assignee: BASF AktiengesellschaftInventors: Dieter Littmann, Thomas Telser, Horst Koch, Wolfgang Huemmer, Martin Meister
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Patent number: 5098806Abstract: Rapid changes in absorption are made within the volume of a photosensitive transparent member that absorbs incident radiation to prevent the photocopy of a document, the original transparency being restored after discontinuance of the incident radiation.Type: GrantFiled: September 22, 1989Date of Patent: March 24, 1992Assignee: Board of Regents, The University of Texas SystemInventor: Jean J. Robillard
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Patent number: 5096935Abstract: The invention relates 6-acyl-(6H)-dibenz[c,e][1,2]oxaphosphorine-6-oxides of the formula ##STR1## wherein each of R.sup.1, R.sup.2 and R.sup.3 may be present one or more times and R.sup.1, R.sup.2 and R.sup.3 represent halogen having an atomic number of from 9 to 35, alkyl or alkoxy each having from 1 to 6 carbon atoms and wherein Ar represents an aromatic hydrocarbon group having from 6 to 10 carbon atoms.The invention further relates to a process for the preparation of the afore-mentioned compounds and polymerizable compositions containing them as an essential ingredient as a photo-initiator. Finally the invention relates to 6-alkoxy-(6H)-dibenz[c,e][1,2]oxaphosphorin of the formula II ##STR2## wherein each of R.sup.1 and R.sup.2 may be present once or more times and R.sup.1 and R.sup.2 represent halogen having an atomic number of from 9 to 35, alkyl or alkoxy each having from 1 to 6 carbom atoms, at least one R.sup.1 being, however, halogen, and wherein R.sup.Type: GrantFiled: October 16, 1990Date of Patent: March 17, 1992Assignee: Hoechst AGInventors: Hans-Jerg Kleiner, Joachim Gersdorf, Udo Bastian
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Patent number: 5079126Abstract: A photohardenable composition comprising an addition polymerizable or crosslinkable material, a photoinitiator composition capable of initiating polymerization or crosslinking of said polymerizable or crosslinkable material, and a compound of the formula ##STR1## wherein Q represents --C.dbd.O or --C--OH; X represents S or N which is unsubstituted or substituted with alkyl or aryl groups;R.sub.1 represents H, alkyl, aryl, alkoxy, bezoyl, arloxy, acyl or monosubstituted amino groups; andR.sub.2 represents H, alkyl or aryl groups is disclosed. The composition is preferably contained in microcapsules and is used in photosensitive imaging systems. The five member aromatic group containing the imine moiety functions to reduce the likelihood of short time scale reciprocity failure of the composition and enable imaging using high intensity radiation sources. An imaging method using the inventive composition is also disclosed.Type: GrantFiled: August 27, 1990Date of Patent: January 7, 1992Assignee: The Mead CorporationInventors: Jesse Hipps, Sr., Claire M. Plageman
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Patent number: 5073477Abstract: Disclosed is a photosensitive resin composition for flexographic printing which has high water developability and good mechanical strength. The resin composition comprises (A) a partially crosslinked copolymer prepared by a radical emulsion polymerization of a specific monomer mixture (B) a linear polymer having a molecular weight of at least 5,000, which has at least 30 mol % of a conjugated diene unit, (C) a basic nitrogen atom-containing compound, (D) a photopolymerizable ethylenically unsaturated monomer, and (E) a photopolymerization inhitiator. The present invention also provides a resin plate for flexographic printing obtained from the above mentioned resin composition and a process for preparing it. The present invention further provides a printing plate obtained from the resin plate and a process for preparing it.Type: GrantFiled: December 4, 1990Date of Patent: December 17, 1991Assignee: Nippon Paint Co., Ltd.Inventors: Hidefumi Kusuda, Katsuji Konishi, Koichi Ueda
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Patent number: 5063257Abstract: A dental glass ionomer cement composition comprises:(a) 5 to 100 parts by weight of a polymer of an .alpha.-.beta. unsaturated carboxylic acid having a weight average molecular weight of 5,000 to 40,000,(b) 5 to 100 parts by weight of a fluoroaluminosilicate glass powder having an average particle size of 0.02 to 10 .mu.m and a specific gravity of 2.4 to 4.0 and capable of reacting with said "polymer of an .alpha.-.beta. unsaturated carboxylic acid having a weight average molecular weight of 5,000 to 40,000",(c) 5 to 100 parts by weight of a polymerizable unsaturated organic compound having at least one CH.sub.2 .dbd.C(R1)--COO--group wherein R1=H or CH.sub.3,(d) 0.01 to 5 parts by weight of a polymerization catalyst,(e) 2 to 50 parts by weight of water,(f) 0.01 to 20 parts by weight of a surface active agent, and(g) 0.01 to 5 parts by weight of a reducing agent, and optionally h. 0 to 50 parts by weight of an inorganic filler having an average particle size of 0.02 to 10 .mu.Type: GrantFiled: December 11, 1989Date of Patent: November 5, 1991Assignee: G-C Dental Industrial Corp.Inventors: Shoji Akahane, Satoshi Tosaki, Yukiharu Kusayanagi, Shigenobu Kusakai, Kazuo Hirota, Kentaro Tomioka
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Patent number: 5057398Abstract: A photopolymerizable composition that contains a polymeric binder, a polymerizable compound and photoinitiator combination comprising an N-heterocyclic compound and a halogen compound corresponding to one of the folowing formulas I and II ##STR1## in which X.sup.1 stands for chlorine or bromine,X.sup.2 and X.sup.3 are identical or different and denote X.sup.1, hydrogen or alkyl groups,Y and Z are identical or different and denote X.sup.1, hydrogen, CN or (A).sub.n --(B).sub.n --D,A is a phenylene group,n is 0 or 1,B is CO or SO.sub.2,D is R, OR, NHR, NH.sub.2, NR.sub.2 or CX.sup.1 X.sup.2 X.sup.3,R is an alkyl, cycloalkyl, aryl or heteroyl radical,W is a five or six-membered heterocyclic ring having from 1 to 3 heteroatoms, which optionally carries substituents and optionally a fused aromatic ring, andm is 1 or 2,is distinguished by an improved light sensitivity.Type: GrantFiled: April 26, 1990Date of Patent: October 15, 1991Assignee: Hoechst AktiengesellschaftInventors: Hans-Dieter Frommeld, Hansjoerg Vollmann
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Patent number: 5055372Abstract: A photohardenable composition comprising a free radical addition polymerizable or crosslinkable compound and an aromatic ketone and a borate salt; and photosensitive materials employing the composition where in one embodiment the composition is microencapsulated.Type: GrantFiled: April 23, 1990Date of Patent: October 8, 1991Assignee: The Mead CorporationInventors: Michael S. Shanklin, Peter Gottschalk, Paul C. Adair
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Patent number: 5051312Abstract: This invention concerns a process for modifying polymer surfaces by contacting the surface with a selected organic modifying agent while irradiating the surface with ultraviolet and/or visible light that can be absorbed by the modifier. Patterns of modified and unmodified surfaces can be produced. Polymers with modified surfaces are useful for absorbing biologically active molecules, composites, printing plates and electronics.Type: GrantFiled: March 29, 1990Date of Patent: September 24, 1991Assignee: E. I. Du Pont de Nemours and CompanyInventor: Klas G. M. Allmer
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Patent number: 5049481Abstract: A photopolymerizable composition comprising (i) a polymerizable compound having an addition polymerizable unsaturated bond, (ii) a compound represented by formula (Ia): ##STR1## a compound represented by formula (Ib): ##STR2## or a compound represented by formula (Ic): ##STR3## wherein A represents an oxygen atom, a sulfur atom, a selenium atom, a tellurium atom, an alkyl- or aryl-substituted nitrogen atom, or a dialkyl-substituted carbon atom; Y.sup.1 represents a hydrogen atom, an alkyl group, a substituted alkyl group, an aryl group, a substituted aryl group, an aralkyl group, an acyl group, an alkoxycarbonyl group, or a substituted alkoxycarbonyl group; R.sup.1 and R.sup.2 each represents a hydrogen atom, an alkyl group having from 1 to 18 carbon atoms, or an alkyl group having from 1 to 18 carbon atoms which is substituted with R.sup.3 O--, ##STR4## or a halogen atom (i.e., F, Cl, Br, and I), wherein R.sup.Type: GrantFiled: December 26, 1989Date of Patent: September 17, 1991Assignee: Fuji Photo Film Co., Ltd.Inventors: Yasuo Okamoto, Tadahiro Sorori
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Patent number: 5045573Abstract: Compounds of the general formula I ##STR1## wherein Z is CR.sup.1 R.sup.2 (OR.sup.3) or phenyl,R.sup.1 being H, C.sub.1-6 -alkyl or phenyl,R.sup.2 being H, C.sub.1-6 -alkyl or C.sub.1-6 -alkoxy andR.sup.3 being H, C.sub.1-6 -alkyl or C.sub.1-6 -alkanoyl andZ' is Y-[(CH.sub.2).sub.m -X].sub.n -,X being CH.sub.2 or 0,Y being OH; COOH or SO.sub.3 H including the alkali metal, alkaline earth metal or ammonium salts thereof and also the salts thereof with organic nitrogen bases; or NRR' in which R and R' are in each case H, C.sub.1-20 -alkyl or C.sub.1-4 -hydroxyalkyl, if appropriate quaternized or in the form of the acid addition salts, andn and m each being the numbers 1-4, are excellently suitable as photoinitiators for the photopolymerization of ethylenically unsaturated compounds, in particular in aqueous systems.Type: GrantFiled: April 13, 1989Date of Patent: September 3, 1991Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Manfred Kohler, Jorg Ohngemach, Gregor Wehner, Jurgen Gehlhaus
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Patent number: 5045434Abstract: A visible radiation sensitive composition comprising:(A) a photosetting resin containing a photosensitive group capable of crosslinking or polymerizing by photoirradiation,(B) a sensitizer represented by the formula (i): ##STR1## wherein R.sub.1 and R.sub.2 are the same or different lower alkyl, and R.sub.3 is a hydrogen atom, lower alkyl group, alkoxyalkyl group, hydroxyalkoxyalkyl group or alkoxycarbonylalkyl group, and(C) a polymerization initiator.Type: GrantFiled: December 18, 1990Date of Patent: September 3, 1991Assignee: Kansai Paint Co., Ltd.Inventors: Ichiro Yoshihara, Motoko Okuhara, Takao Yamamoto, Naozumi Iwasawa, Yasuo Doi, Tsukasa Ohyama, Kazuhiko Murayama, Yoriaki Matsuzaki, Susumu Kasamatsu, Keisuke Takuma, Kimitoshi Kato
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Patent number: 5043362Abstract: Water-processable screenprinting stencils and resists are based upon photopolymerizable systems in which the hydrogen donor compound is a modified polyvinylalcohol having pendant dialkylamino groups.Type: GrantFiled: June 28, 1988Date of Patent: August 27, 1991Assignee: Autotype International LimitedInventors: Ross A. Balfour, John A. Sperry
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Patent number: 5034429Abstract: A photopolymerizable composition comprising (a) an addition polymerizable compound having a boiling point of 100.degree. C. or high under an atmospheric pressure, (b) a photoinitiator, and (c) a benzene derivative can provide a cured film having high strength suitable for producing, e.g. printed circuit boards.Type: GrantFiled: June 2, 1988Date of Patent: July 23, 1991Assignee: Hitachi Chemical Co., Ltd.Inventors: Makoto Kaji, Nobuyuki Hayashi, Futami Kaneko
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Patent number: 5028638Abstract: In a dental composite containing a polymerizable (meth)acrylic compound, photoinitiator, accelerator, inorganic filler and conventional auxiliaries, the improvement wherein the composite by weight comprises about(a) 10-50% of at least one monomer which contains at least 2 polymerizable (meth)acrylic acid groups,(b) 5-80% of a glass or a glass ceramic which has an average particle size of between about 0.1 and 10 .mu.m and has been post-treated with .gamma.-methacryloxypropyltrimethoxysilane up to a carbon content of between about 0.5 and 2.5% by weight,(c) 2-10% of a surface-treated microfiller and(d) 0.1-5% of a photoactivator consisting of a mixture of camphorquinone and p-dialkylaminobenzenesulphonamide. The composition has a long pot life and good surface color when cured.Type: GrantFiled: January 22, 1990Date of Patent: July 2, 1991Assignee: Bayer AktiengesellschaftInventors: Renate Heid, Jens Winkel, Heiko Herold, Peter Schwabe, Werner Finger, Wolfgang Podszun
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Patent number: 5026625Abstract: Titanocenes containing two 5-membered cyclodienyl gropus, for example cyclopentadienyl, and one or two 6-membered carbocyclic or 5- or 6-membered heterocyclic aromatic rings which are substituted by a fluorine atom in at least one of the two ortho-positions to the titanium-carbon bond and contain, as further substituents, a substituted amino radical, are suitable as photoinitiators for radiation-induced polymerization of ethylenically unsaturated compounds.Type: GrantFiled: November 21, 1988Date of Patent: June 25, 1991Assignee: Ciba-Geigy CorporationInventors: Martin Riediker, Eginhard Steiner, Harry Beyeler, Franciszek Sitek, Rinaldo Husler
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Patent number: 5026740Abstract: The invention relates to the use of a new class of sulphurated derivatives of aromatic-aliphatic or aliphatic ketones as a) polymerization or crosslinking photoinitiators for transparent or pigmented mixtures containing ethylenically unsaturated photopolymerizable compounds, in particular for obtaining polyacrylates, b) photochemically releasable latent acid catalysts, useful for crosslinking systems polycondensable by acid catalysis, of the type comprising etherified aminoplasts together with compounds containing hydroxyl, carboxyl, amido, amino and other functionalities.Said sulphurated derivatives enable manufactured articles to be obtained with exceptionally clear color while maintaining photochemical reactivity at high levels.Type: GrantFiled: July 15, 1988Date of Patent: June 25, 1991Assignee: Fratelli Lamberti S.p.A.Inventors: Giuseppe Li Bassi, Luciano Cadona, Carlo Nicora
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Patent number: 5019482Abstract: A photosensitive composition comprising:(a) a polymer(b) 1 to 20% by weight, based on the weight of polymer (a), of a compound having a terminal ethylenically unsaturated group;(c) 0.1 to 20% by weight, based on the weight of polymer (a), of an oxime ester compound(d) 0.01 to 10% by weight, based on the weight of polymer (a), of a coumarin compound having a wave length of the absorption peak of 330 to 550 nm; has high photosensitivity to an actinic light of a wave length of 400 to 500 nm and is capable of forming heat-resistant images, patterns or films.Type: GrantFiled: August 5, 1988Date of Patent: May 28, 1991Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Hideo Ai, Nobuhiko Suga, Satoshi Ogitani, Hideaki Takahashi, Akihiko Ikeda
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Patent number: 5019481Abstract: An aqueous base developable negative resist composition comprising a phenolic resin, a radio-chemical acid generator and a small molecule which upon irradication and postbake reacts with the phenolic resin to decrease its rate of dissolution.Type: GrantFiled: September 25, 1989Date of Patent: May 28, 1991Assignee: International Business Machines CorporationInventor: Hiroshi Ito
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Patent number: 5017626Abstract: A visible light-curing polyester resin composition comprises an unsaturated polyester resin and a photocuring agent composed of an .alpha.-diketone, a benzyidimethyl ketal, and at least one member selected from the group consisting of (1) 2-(dimethylamino)-ethyl benzoate, (2) 2-(dimethylamino)-ethyl benzoate plus a peroxy ketal, and (3) a peroxy ketal plus a tertiaryamine.Type: GrantFiled: September 30, 1988Date of Patent: May 21, 1991Assignee: Nippon Oil & Fats Co., Ltd.Inventors: Yoshihiro Tomura, Shigeki Banno
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Patent number: 5011560Abstract: A method of adhesion which comprises applying a two-step reactive type tacky adhesive agent comprising (1) a non-photopolymerizable epoxy resin or isocyanate compound, (2) a curing agent therefor and (3) a compound having at least one photopolymerizable vinyl group in one molecule onto a substrate, irradiating the whole applied surface with light to develop the tackiness, and sticking the substrate together to a material to be bonded, while the tackiness is retained, followed by curing.The method provides excellent green bonding strength and can permit the satisfactory adhesion without clamping, and can be particularly suitably utilized in the adhesion of materials to be bonded which have a curved surface difficult to be clumped.Type: GrantFiled: August 19, 1988Date of Patent: April 30, 1991Assignee: Takeda Chemical Industries, Ltd.Inventors: Yoshikazu Nakai, Tsutomu Kubota