Hydroxyl Or Carbonyl Group Containing As Sole Functional Groups Patents (Class 430/918)
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Patent number: 8178277Abstract: The present invention provides coating compositions comprising (i) a) a compound containing a free carbonyl group and b) a nucleophile or (ii) a compound containing a free carbonyl group, which compound is substituted with one or more nucleophilic groups. The present invention also provides a process for the preparation of these compositions, substrates coated with these compositions and a process for their preparation, a process for preparing marked substrates using these compositions, and marked substrates obtainable by the latter process.Type: GrantFiled: December 21, 2007Date of Patent: May 15, 2012Assignee: Datalase Ltd.Inventors: Jonathan Campbell, Adolf Käser
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Patent number: 7550253Abstract: A resist film made of a chemically amplified resist is formed on a substrate. Subsequently, a barrier film for preventing a component of the resist film from eluting into an immersion liquid or preventing the immersion liquid from permeating into the resist film is formed on the resist film. Thereafter, with an immersion liquid provided on the barrier film, pattern exposure is carried out by selectively irradiating the resist film with exposing light through the barrier film. Then, after removing the barrier film, the resist film having been subjected to the pattern exposure is developed, so as to form a resist pattern made of the resist film.Type: GrantFiled: February 16, 2005Date of Patent: June 23, 2009Assignee: Panasonic CorporationInventors: Masayuki Endo, Masaru Sasago
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Patent number: 7482111Abstract: It is an object of the present invention to provide a process capable of precisely producing a plated shaped article of a large thickness such as a bump or a wiring, a negative radiation-sensitive resin composition which is preferably used for the process and has excellent sensitivity and resolution, and a transfer film using the composition. The above object is achieved by a negative radiation-sensitive resin composition comprising (A) a polymer containing structural units represented by the following formula (1) and/or the following formula (2), (B) a compound having at least one ethylenically unsaturated double bond and (C) a radiation-sensitive radical polymerization initiator, and by forming a negative radiation-sensitive resin film using the composition.Type: GrantFiled: March 24, 2005Date of Patent: January 27, 2009Assignee: JSR CorporationInventors: Kouji Nishikawa, Tooru Kimura, Shin-ichiro Iwanaga
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Patent number: 7235349Abstract: A process of forming ultra fine patterns using bottom anti-reflective coating containing acid generator. More particularly, a process of forming vertical patterns using an organic bottom anti-reflective coating containing excessive amount of acid generator, in order to prevent formation of sloping patterns due to photoresist resins absorbing wavelength of light used as light sources during lithography process using light sources such as KrF, ArF, VUV, EUV, E-beam and ion beam, even when photoresist resins having high absorbance to light source are used.Type: GrantFiled: December 29, 2005Date of Patent: June 26, 2007Assignee: Hynix Semiconductor Inc.Inventors: Sung Koo Lee, Jae Chang Jung, Geun Su Lee, Ki-Soo Shin
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Patent number: 7229739Abstract: The invention generally relates to positive-working coating compositions and to a substrate formed with a coating of that composition. Advantageous versions of the invention provide an infrared imageable, positive lithographic printing plate having a coating comprising a hydroxy substituted polymer, a diphenylcarbinol solubility suppressing compound and an infrared radiation absorbing compound.Type: GrantFiled: May 25, 2005Date of Patent: June 12, 2007Assignee: Anocoil CorporationInventors: Paul A. Perron, Brian L. Anderson, William J. Ryan
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Patent number: 6864040Abstract: The present invention relates to IR-sensitive compositions containing an initator system comprising: (a) at least one compound capable of absorbing IR radiation selected from triarylamine dyes, thiazolium dyes, indolium dyes, oxazolium dyes, cyanine dyes, polyaniline dyes, polypyrrole dyes, polythiophene dyes and phthalocyanine pigments (b) at least one compound capable of producing radicals selected from polyhaloalkyl-substituted compounds (c) at least one polycarboxylic acid represented by the following formula I wherein Y is selected from the group consisting of O, S and NR7, each of R4, R5 and R6 is independently selected from the group consisting of hydrogen, C1-C4 alkyl, aryl which is optionally substituted, —COOH and NR8CH2COOH, R7 is selected from the group consisting of hydrogen, C1-C6 alkyl, —CH2CH2OH, and C1-C5 alkyl substituted with -COOH, R8 is selected from the group consisting of —CH2COOH, —CH2OH and —(CH2)2N(CH2COOH)2 and r is 0, 1, 2 or 3 with the proviso that at least one of R4, R5, RType: GrantFiled: April 11, 2001Date of Patent: March 8, 2005Assignee: Kodak Polychrome Graphics LLCInventors: Ursula Müller, Tobias Wittig, Hans-Joachim Timpe
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Patent number: 6838222Abstract: A photopolymerizable composition that is cured with visible light or an infrared laser and is used as a recording layer in a negative planographic printing plate precursor. The photopolymerizable composition is cured by exposure and includes (A) a polymerizable compound that is solid at 25° C. and has at least one radical-polymerizable ethylenically unsaturated double bond in a molecule, (B) a radical polymerization initiator, (C) a binder polymer and, as required, (D) a compound generating heat by infrared exposure.Type: GrantFiled: February 14, 2002Date of Patent: January 4, 2005Assignee: Fuji Photo Film Co., Ltd.Inventors: Keitaro Aoshima, Kazuhiro Fujimaki
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Patent number: 6686121Abstract: A resist composition is prepared by reacting an alkali-soluble polymer having a phenolic hydroxyl or carboxyl groups with a vinyl ether compound in an aprotic solvent, such as propylene glycol monomethyl ether acetate, in the presence of an acid catalyst, suspending the reaction by the addition of a base, and directly adding a photoacid generator to the reaction solution. When a dialkyl dicarbonate is used in stead of the vinyl ether compound, a resist composition is prepared by carrying out the reaction in the presence of a basic catalyst and adding a photoacid generator directly to the reaction. Thus resist compositions can be prepared without isolating or purifying an alkali-soluble polymer which has been substituted by a catalytic reaction.Type: GrantFiled: April 2, 2001Date of Patent: February 3, 2004Assignee: Clariant Finance (BVI) LimitedInventors: Hiroshi Okazaki, Georg Pawlowski, Satoru Funato, Yoshiaki Kinoshita, Yuko Yamaguchi
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Publication number: 20030118939Abstract: The present invention provides an IR-sensitive composition, which includes: a polymeric binder; and a free radical polymerizable system consisting of: at least one component selected from unsaturated free radical polymerizable monomers, oligomers which are free radical polymerizable and polymers containing C═C bonds in the backbone and/or in the side chain groups; and an initiator system, which includes: (a) at least one compound capable of absorbing IR radiation; (b) at least one compound capable of producing radicals; and (c) at least one carboxylic co-initiator, provided that the total acid number of the polymeric binder is 70 mg KOH/g or less. The present invention further provides a printing plate precursor, a process for preparing the printing plate and a method of producing an image.Type: ApplicationFiled: November 9, 2001Publication date: June 26, 2003Applicant: KODAK POLYCHROME GRAPHICS, L.L.C.Inventors: Heidi Munnelly, Paul West
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Patent number: 6284427Abstract: A resist composition is prepared by reacting an alkali-soluble polymer having a phenolic hydroxyl or carboxyl groups with a vinyl ether compound in an aprotic solvent, such as propylene glycol monomethyl ether acetate, in the presence of an acid catalyst, suspending the reaction by the addition of a base, and directly adding a photoacid generator to the reaction solution. When a dialkyl dicarbonate is used in stead of the vinyl ether compound, a resist composition is prepared by carrying out the reaction in the presence of a basic catalyst and adding a photoacid generator directly to the reaction. Thus resist compositions can be prepared without isolating or purifying an alkali-soluble polymer which has been substituted by a catalytic reaction.Type: GrantFiled: August 5, 1999Date of Patent: September 4, 2001Assignee: Clariant Finance (BVI) LimitedInventors: Hiroshi Okazaki, Georg Pawlowski, Satoru Funato, Yoshiaki Kinoshita, Yuko Yamaguchi
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Patent number: 6255034Abstract: A radiation sensitive composition contains (A) a colorant, (B) a binder polymer, (C) a polyfunctional monomer and (D) a carboxyl group-containing monofunctional monomer, an amide group-containing monoethylenically unsaturated monomer, a monoethylenically unsaturated monomer having a cyclic amide group or cyclic imide group or a phenyl group-containing (meth)acrylate, and (E) a photopolymerization initiator. The composition is useful for producing a color filter for use in color liquid crystal display device, color image pick-up elements etc.Type: GrantFiled: September 8, 1998Date of Patent: July 3, 2001Assignee: JSR CorporationInventors: Satoshi Shimada, Tomio Nagatsuka, Hiroaki Nemoto, Atsushi Kumano
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Patent number: 5773194Abstract: A light sensitive composition comprising (a) a vinyl type polymer having a unit represented by the following Formula (1) and a carboxyl group, (b) a monomer, oligomer or polymer containing at least one polymerizable double bond in its molecule, (c) a photopolymerization initiator and (d) a polymerization inhibitor capable of trapping a radical, ##STR1##Type: GrantFiled: August 29, 1996Date of Patent: June 30, 1998Assignee: Konica CorporationInventors: Ryoji Hattori, Tatsuichi Maehashi, Takaaki Kuroki, Sota Kawakami
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Patent number: 5698373Abstract: The present invention relates to a photosensitive relief or intaglio printing plate comprising a base and a photocurable photosensitive layer formed on the base, the photocurable photosensitive layer containing a dye precursor which forms a dye upon irradiation of actinic light. A relief (convex) pattern or a concave pattern can be recognized by coloring, thereby facilitating the printing plate inspecting work. The developing solution used is not colored or contaminated.Type: GrantFiled: August 2, 1994Date of Patent: December 16, 1997Assignee: Toray Industries, IncorporatedInventors: Junichi Fujikawa, Takao Kinashi, Shigetora Kashio, Yasuko Yokoyama
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Patent number: 5543262Abstract: A light sensitive composition which is capable of photopolymerization which includes a photopolymerizable compound a free radical generating component and a benzanthrone or substituted benzanthrone which substantially prevents photopolymerization when the light sensitive composition is exposed to actinic radiation below a threshold amount but permits photopolymerization when the light sensitive composition is exposed to actinic radiation above a threshold amount. This achieves a gate effect which eliminates or decreases unwanted partial exposure in the nonimage areas and hence improves reproduction quality.Type: GrantFiled: February 24, 1995Date of Patent: August 6, 1996Assignee: International Paper CompanyInventors: Maria T. Sypek, John R. Delude, Paul A. Perron
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Patent number: 5512417Abstract: A positive resist composition comprising a poly(p-hydroxystyrene) as matrix resin which is synthesized by an anionic polymerization method and has a weight average molecular weight of from 8,000 to 20,000, bis(p-t-butoxycarbonylmethyl)thymolphthalein as dissolution inhibitor, bis(p-t-butylphenyl)iodonium triflate as acid generator; a compound which contains one amino group and one carboxyl group to function as acid deactivator and propylene glycol monomethyl ether acetate as organic solvent.Type: GrantFiled: February 14, 1995Date of Patent: April 30, 1996Assignees: Shin-Etsu Chemical Co., Ltd., Nippon Telegraph and Telephone Corp.Inventors: Hiroshi Ban, Akinobu Tanaka, Fujio Yagihasi, Jun Watanabe, Minoru Takamizawa
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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: 5262278Abstract: Storage-stable solutions of film forming carboxyl-containing copolymers, from 5 to 80% of whose carboxyl groups have been reacted with glycidyl (meth)acrylate, in an inert organic solvent or solvent mixture additionally contain a phosphoric ester of a hydroxyalkyl (meth)acrylate and, if required, orthophosphoric acid, and photosensitive coatings which contain a photoinitiator, ethylenically unsaturated organic monomeric compounds which can be subjected to free radical polymerization and, if required, plasticizers, dyes, dye precursors and thermal polymerization inhibitors are produced in such storage-stable solutions.They are particularly suitable for the production of offset printing plates.Type: GrantFiled: January 17, 1992Date of Patent: November 16, 1993Assignee: BASF AktiengesellschaftInventors: Harald Lauke, Thomas Loerzer, Axel Sanner, Joachim Roser
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Patent number: 5254437Abstract: Disclosed is a photosensitive resin plate which effectively prevents dot gain by covering the photosensitive resin layer with a specific matte layer. The photosensitive resin plate comprises a substrate, a photosensitive resin layer formed on the substrate and a resin matte layer formed on the photosensitive resin layer, wherein the resin matte layer contains a polymerization inhibiting material.Type: GrantFiled: February 8, 1993Date of Patent: October 19, 1993Assignee: Nippon Paint Co., Ltd.Inventors: Koichi Ueda, Katsuji Konishi, Kazunori Kanda
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Patent number: 5230981Abstract: An image recording process is disclosed. The process comprises the steps of: imagewise exposing silver halide to light to form a latent image of the silver halide; developing the formed latent image of the silver halide with a reducing agent; and conducting substantially uniform light exposure in the presence of a photopolymerization initiator and an ethylenically unsaturated polymerizable compound to form a polymer image. According to the present invention, the reducing agent forms an oxidation product having a function as a polymerization inhibitor after the development. Thus a polymer image is formed within the area where the oxidation product of the reducing agent has not been formed. The reducing agent has the following formula [I]: ##STR1## in which R.sup.1 is an alkyl group, an aryl group or a heterocyclic group; R.sup.2 is an organic group which is attached to the benzene ring by a hetero-atom having a lone pair of electrons; R.sup.Type: GrantFiled: February 21, 1990Date of Patent: July 27, 1993Assignee: Fuji Photo Film Co., Ltd.Inventors: Naoki Saito, Makoto Yamada
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Patent number: 5164278Abstract: Acid sensitized photoresists with enhanced photospeed are provided. The photoresist compositions include a polymer binder and/or a polymerizable compound and an acid sensitive group which enables patterning of the resist composition, and acid generating photoinitiator, and an hydroxy aromatic compound which enhances the speed of the resist composition under imaging radiation.Type: GrantFiled: March 1, 1990Date of Patent: November 17, 1992Assignee: International Business Machines CorporationInventors: William R. Brunsvold, Christopher J. Knors, Melvin W. Montgomery, Wayne M. Moreau, Kevin M. Welsh
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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: 5091283Abstract: A photo curable diallyl phthalate resin composition characterized by containing 0.1 to 10 parts by weight of an agent for preventing back side undesirable curing and 20 to 100 parts by weight of a filler per 100 parts by weight of a diallyl phthalate prepolymer is particularly suitable for a partly additive process for forming a solder resist effective for preventing back side undesirable curing by ultraviolet light and having resistance to release of substances from the solder resist for deteriorating properties of plated copper film as well as for giving good mechanical properties.Type: GrantFiled: March 27, 1990Date of Patent: February 25, 1992Assignee: Hitachi, Ltd.Inventors: Isamu Tanaka, Hitoshi Oka, Makio Watanabe, Hiroshi Kikuchi, Shinichiro Imabayashi, Yukihiro Taniguti
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Patent number: 5026626Abstract: A photopolymeriziable composition which comprises poly butane diol diacrylate, a photoinitiator and a binding resin. Upon coating the composition onto a substrate a photographic element is formed which does not require the presence of an oxygen barrier layer.Type: GrantFiled: June 14, 1990Date of Patent: June 25, 1991Inventors: Oliver A. Barton, James D. Wright
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Patent number: 5011762Abstract: A photosensitive composition which is suitable for free radical polymerization systems initiated by ultraviolet light, particularly useful in UV-curing coating and image transfer systems such as printing plates and photoresists. Among the above mentioned applications, systems in which the photosensitive layer has no protective film to insulate it from the air shows the greatest improvement in photosensitivity.Type: GrantFiled: August 14, 1990Date of Patent: April 30, 1991Assignee: Industrial Technology Research InstituteInventors: Rong-Jer Lee, Chein-Dhau Lee, Wen-Shin Shen
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Patent number: 4952482Abstract: A photopolymerizable composition which comprises poly butane diol diacrylate, a photoinitiator and a binding resin. Upon coating the composition onto a substrate a photographic element is formed which does not require the presence of an oxygen barrier layer.Type: GrantFiled: July 5, 1989Date of Patent: August 28, 1990Assignee: Hoechst Calanese CorporationInventors: Oliver A. Barton, James D. Wright
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Patent number: 4902603Abstract: A light-sensitive mixture useful as a negative-working photoresist composition comprising:(a) at least one novolak resin; and(b) at least one 6-acetoxy cyclohexadienone compound of the formula (I) below: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are individually selected from hydrogen and lower alkyl groups having from 1 to 4 carbon atoms with the proviso that at least three of the R.sub.1 to R.sub.5 groups are lower alkyl groups.Type: GrantFiled: October 5, 1987Date of Patent: February 20, 1990Assignee: Olin CorporationInventors: Sydney G. Slater, Stanley A. Ficner
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Patent number: 4894314Abstract: Photoinitiator compositions are disclosed which contain 3,3'-carbonyl bis(7-diethylaminocoumarin); an alkyl ester of a p-dialkylamino benzoic acid; and either camphorquinone or a 2,4,5-triphenylimidazolyl dimer. Photoinitiators are also provided which contain 3,3'-carbonyl bis(7-diethylaminocoumarin); an alkyl ester of a p-dialkylamino benzoic acid; camphorquinone and a 2,4,5-triphenylimidazolyl dimer. These latter photoinitiators are particularly useful in photopolymerizable compositions which are polymerized by exposure to visible laser light.Type: GrantFiled: November 16, 1988Date of Patent: January 16, 1990Assignee: Morton Thiokol, Inc.Inventors: Robert Barr, Leo Roos, Lawrence Crane
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Patent number: 4882259Abstract: An imaging material of the type in which a radiation sensitive composition is encapsulated in a plurality of microcapsules and exposure controls the release of the internal phase from the microcapsules wherein the internal phase of the microcapsules includes a solid diluent.Type: GrantFiled: April 22, 1986Date of Patent: November 21, 1989Assignee: The Mead CorporationInventors: Joseph G. O'Connor, Paul C. Adair
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Patent number: 4707431Abstract: This invention relates to an optical information recording medium comprising a substrate provided at least with an underlayer and a recording layer thereon, said underlayer being prepared by curing a light-curable composition containing a reducing agent, a photo-polymerization initiator and acrylate monomer and/or methacrylate monomer and/or their corresponding oligomer.Type: GrantFiled: October 25, 1985Date of Patent: November 17, 1987Assignee: Ricoh Co., Ltd.Inventor: Masaakira Umehara
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Patent number: 4699859Abstract: A reducible image-containing element which comprises a support material and a photopolymerized layer provided thereon, said photopolymerized layer having an image area which is cured at the upper part and not cured at the lower part, said non-cured lower part containing at least one of polyvalent phenols and their derivatives in an amount effective in preventing said non-cured lower part from curing.Type: GrantFiled: September 7, 1984Date of Patent: October 13, 1987Assignee: Toyo Boseki Kabushiki KaishaInventors: Toshiaki Fujimura, Yoshio Katoh, Satoshi Imahashi, Koichi Seto, Shinichi Tanaka
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Patent number: 4693960Abstract: A composition containing a polysiloxane having a polymerizable ethylenically unsaturated group, and 2,2-dimethoxy-2-phenyl acetophenone as an ultraviolet light sensitizer; and use thereof in lithography.Type: GrantFiled: November 7, 1986Date of Patent: September 15, 1987Assignee: International Business Machines CorporationInventors: Edward D. Babich, Michael Hatzakis, John J. Liutkis, Juri R. Parasczak, Jane M. Shaw
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Patent number: 4680251Abstract: The invention relates to a process for the ozone protection of an imagewise exposed and developed photopolymer flexographic printing plate, having an elastomeric, thermoplastic polymeric binder, which comprises applying to the exposed and developed surface of the flexographic printing plate at least one known liquid polyether of the formulas: ##STR1## wherein R.sub.1 =H, or methylR.sub.2 =H, alkyl or alkylene with C.sub.12 -C.sub.18, and saturated and unsaturated fatty acid radicals with C.sub.12 -C.sub.18.p=1-4and wherein n, m and m.sub.1-4 and x, y, and z are so selected that the molecular weight (M.sub.n) of the molecule is about 500 to 5000.Type: GrantFiled: April 18, 1985Date of Patent: July 14, 1987Assignee: E. I. Du Pont de Nemours and CompanyInventor: Manfred Schober
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Patent number: 4517278Abstract: A photosensitive resin composition useful for preparation of flexographic printing plates, which comprises syndiotactic 1,2-polybutadiene, an ethylenically unsaturated monomer and a photo-polymerization initiator, the syndiotactic 1,2-polybutadiene having an average molecular weight of from about 10,000 to 300,000, a 1,2-unit content of at least about 80 percent and a crystallinity of about 10 to 30 percent, said ethylenically unsaturated monomer being an ester of acrylic or methacrylic acid with an alkanol having from 4 to 20 carbon atoms, and the photo-polymerization initiator being benzoin or an alkyl ether thereof. The photosensitive resin composition, when formed into sheets, exhibits satisfactory resistance to liquids used for washing out the uncured areas and at also to aqueous or alcoholic printing inks, thereby producing patterns in relief that give excellent overall sharpness. It also possesses desired hardness and elasticity for flexographic printing plates.Type: GrantFiled: August 13, 1982Date of Patent: May 14, 1985Assignee: Nippon Paint Co., Ltd.Inventor: Kiyomi Sakurai
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Patent number: 4288527Abstract: This invention is directed to dual UV and heat activated compositions comprising(1) a liquid, ethylenically unsaturated monomer, oligomer or prepolymer of the formula: ##STR1## wherein R is H or CH.sub.3, R.sub.1 is an organic moiety and n is 2 to 4, hereinafter referred to as the ethylenically unsaturated compound,(2) a photoinitiator, and(3) a substituted or unsubstituted pinacolThe exposure to UV radiation and heat in seriatim or simultaneously results in a cured solid product which can be utilized as coatings, gaskets, sealants, resists and the like.Type: GrantFiled: August 13, 1980Date of Patent: September 8, 1981Assignee: W. R. Grace & Co.Inventor: Charles R. Morgan
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Patent number: 4243740Abstract: A sensitive composition comprising polymethyl isopropenyl ketone of limited molecular weight and a compound of a given general formula. The formation of a pattern of less than 1 .mu.m is made possible by employing ultraviolet rays of wave lengths of 100-350 nm in place of those of 350-450 nm utilized in conventional processes. The sensitive composition is highly sensitive to ultraviolet rays in said wave range and reproduces a fine pattern precisely.Type: GrantFiled: March 16, 1979Date of Patent: January 6, 1981Assignee: Tokyo Ohka Kogyo Kabushiki KaishaInventors: Minoru Tsuda, Yoichi Nakamura, Hideo Nagata, Hisashi Nakane
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Patent number: 4202742Abstract: An initiator-free composition is prepared of an ethylenically unsaturated monomer and the inhibitor parabenzoquinone or hydroquinone. The composition is irradiated with light having a wavelength within the absorption spectrum of the inhibitor, other than ultraviolet. The light causes the inhibitor to produce a reactive species which initiates polymerization.Type: GrantFiled: April 30, 1979Date of Patent: May 13, 1980Assignee: Westinghouse Electric Corp.Inventor: Peter M. Castle