Processes Involving An Ethylenically Unsaturated Material Derived From Poly 1,2-epoxide As Reactant Or A Solid Polymer; Or Compositions Thereof Patents (Class 522/100)
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Patent number: 5218009Abstract: Compounds of the formula I ##STR1## in which at least one of the radicals R.sub.1, R.sub.2 and R.sub.3 is a substituted alkyl radical or cycloalkyl radical, or R.sub.1 and R.sub.2 together with the phosphorus atom form a monocyclic or tricyclic ring, are effective photoinitiators for the photopolymerization of ethylenically unsaturated compounds.Type: GrantFiled: August 28, 1991Date of Patent: June 8, 1993Assignee: Ciba-Geigy CorporationInventors: Werner Rutsch, Kurt Dietliker, Roger G. Hall
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Patent number: 5204378Abstract: The fluorine-containing epoxy(meth)acrylate resin of the invention is represented by the following general formula (I). ##STR1## wherein R.sub.f is selected from the group consisting of --.phi.--C(CF.sub.3).sub.2 --.phi.--(where .phi. stands for ##STR2## --C(CF.sub.3).sub.2 --.phi.'--C(CF.sub.3).sub.2 --(where .phi.' stands for and --CH.sub.2 (CF.sub.2).sub.6 CH.sub.2 --; n is zero or a positive interger; and X is hydrogen or methyl group. The resin of the invention may be prepared by reacting a diglycidyl ether of a fluorine-containing hydrocarbon (R.sub.f) with acrylic acid or methacrylic acid. Further provided is an adhesive composition comprising the aforementioned fluorine-containing epoxy(meth)acrylate resin and a photo-polymerization initiator, which can be cured at room temperature within a short time by irradiation with UV rays to form a cured product having a refractive index N.sub.D.sup.20 ranging from 1.434 to 1.532.Type: GrantFiled: March 18, 1991Date of Patent: April 20, 1993Assignee: Nippon Telegraph and Telephone CorporationInventors: Tohru Maruno, Shigeki Ishibashi, Kouzaburou Nakamura
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Patent number: 5202360Abstract: An adhesive composition comprising a photopolymerization initiator or curing agent and the compound represented by the formula (I) ##STR1## wherein M is a divalent organic group comprising at least one substituted or unsubstituted alicyclic hydrocarbon group or a divalent organic group comprising at least two substituted or unsubstituted aromatic hydrocarbon groups, the alicyclic hydrocarbon group or aromatic hydrocarbon group may be linked by O, S or CH.sub.2 or may form a condensed ring, n is zero or a positive number.Type: GrantFiled: July 29, 1991Date of Patent: April 13, 1993Assignees: Daiken Industries, Ltd., Nippon Telegraph & Telephone Corp.Inventors: Akira Ohmori, Yoshiki Shimizu, Motonobu Kubo, Kouzaburou Nakamura, Tohru Maruno, Norio Murata, Hideo Kobayashi
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Patent number: 5200436Abstract: The present invention provides novel siloxane iniferter compounds, block copolymers made therewith, and a method of making the block copolymers. The siloxane iniferter compounds can be represented by the formula ##STR1## wherein T and X are organic groups selected so that the T-X bond is capable of dissociating upon being subjected to an appropriate energy source to form a terminator free radical of the formula T.multidot. and an initiator free radical;R.sub.1, R.sub.2, R.sub.5 and R.sub.6 are monovalent moieties selected from the group consisting of hydrogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy and aryl which can be the same or are different;R.sub.3 and R.sub.4 are monovalent moieties which can be the same or different selected from the group consisting of hydrogen, C.sub.1-4 alkyl, C.sub.Type: GrantFiled: July 25, 1991Date of Patent: April 6, 1993Assignee: Minnesota Mining and Manufacture CompanyInventors: Ramesh C. Kumar, Milton H. Andrus, Jr., Miecyzslaw H. Mazurek
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Patent number: 5200437Abstract: This invention relates to coating compositions containing the alk-1-enyl ether reaction product of a hydroxylated compound, an alk-1-enyloxy oxirane and from 0 to 95% of an alkyl epoxide.Type: GrantFiled: January 6, 1992Date of Patent: April 6, 1993Assignee: ISP Investments Inc.Inventors: James A. Dougherty, Fulvio J. Vara, Jeffrey S. Plotkin, Paul D. Taylor, Kolazi S. Narayanan
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Patent number: 5196296Abstract: Epoxy acrylate resins of this invention having a structure of the general formula (I) ##STR1## in which R is hydrogen or a lower alkyl group, R' is hydrogen or methyl group, and n is an integer from 0 to 20 are heat-resistant, solvent-soluble, and photosensitive and photosensitive resin compositions containing said epoxy acrylate resins as main component exhibit high photosensitivity in addition to strong adhesion to substrates, good resistance to heat and chemicals, and good mechanical and electrical properties and are useful as materials for forming insulation films for multilayer devices and protective films for image sensors and as protective films for solder resists, plating resists, and color filters.Type: GrantFiled: July 26, 1990Date of Patent: March 23, 1993Assignees: Nippon Steel Corporation, Nippon Steel Chemical Co., Ltd.Inventors: Kazuhiro Watanabe, Takero Teramoto
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Patent number: 5196487Abstract: A corrosion preventive resin having in the molecule at least one chelate forming group selected from among groups represented by the formula ##STR1## wherein R.sup.1 and R.sup.2 are the same or different and are each a hydrogen atom or alkyl having 1 to 8 carbon atoms, and groups represented by teh general formula ##STR2## wherein R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are the same or different and are each a hydrogen atom, alkyl having 1 to 8 carbon atoms or a group forming a bivalent o-phenylene group along with two carbon atoms attached thereto. A photopolymerizable composition which includes (a) a resin having in the molecule at least one mole of polymerizable double bond per 1000 g of the resin and having per molecule at least one chelate forming group selected from among the groups represented by formula (II) and formula (III), and (b) a photopolymerization initiator is also disclosed.Type: GrantFiled: June 10, 1991Date of Patent: March 23, 1993Assignee: Kansai Paint Company, LimitedInventors: Hideo Kogure, Heihachi Murase, Naozumi Iwasawa
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Patent number: 5194516Abstract: The viscosity of copolymers of a) ethylene and C.sub.1 -C.sub.8 acrylate or methacrylates or b) ethylene, vinyl esters of C.sub.1 -C.sub.4 carboxylic acids, and another comonomer selected from the group consisting of carbon monoxide, acrylic acid, methacrylic acid, or a glycidyl ester of acrylic or methacrylic acid is increased, while maintaining gel content at a level of less than 3%, by treatment with a free radical generating agent.Type: GrantFiled: October 1, 1991Date of Patent: March 16, 1993Assignee: E. I. Du Pont de Nemours and CompanyInventors: John R. Fisher, Jerald R. Harrell, Wolfgang Honsberg, John W. Paul
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Patent number: 5191039Abstract: The fluorine-containing epoxy(meth)acrylate resin of the invention is represented by the following general formula (I). ##STR1## wherein R.sub.f is selected from the group consisting of --.phi.--C(CF.sub.3).sub.2 --.phi.-- (where .phi. stands for ##STR2## --C(CF.sub.3).sub.2 --.phi.'--C(CF.sub.3).sub.2 -- (where .phi.' stands for ##STR3## and --CH.sub.2 (CF.sub.2).sub.6 CH.sub.2 --; n is zero or a positive integer; and X is hydrogen or methyl group. The resin of the invention may be prepared by reacting a diglycidyl ether of a fluorine-containing hydrocarbon (R.sub.f) with acrylic acid or methacrylic acid. Further provided is an adhesive composition comprising the aforementioned fluorine-containing epoxy(meth)acrylate resin and a photo polymerization initiator, which can be cured at room temperature within a short time by irradiation with an UV ray to form a cured product having a refractive index n.sub.D.sup.20 ranging from 1.434 to 1.532.Type: GrantFiled: May 2, 1991Date of Patent: March 2, 1993Assignee: Nippon Telegraph and Telephone CorporationInventors: Tohru Maruno, Shigeki Ishibashi, Kouzaburou Nakamura
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Patent number: 5182316Abstract: A curable composition, the cure of which can be monitored optically, comprises at least one of a hydride curable silicone, an ethylenically unsaturated compound, and a cationically polymerizable monomer, and as cure monitor dibenzofulvene or derivative thereof. The cure monitor is a latent fluorophore which reacts under the cure conditions to form a UV-detectable fluorophore.The invention also provides a method for measuring degree of cure of a polymeric material which can be a coating or an article.Type: GrantFiled: November 26, 1991Date of Patent: January 26, 1993Assignee: Minnesota Mining and Manufacturing CompanyInventors: Robert J. DeVoe, Katherine A. Brown-Wensley, George V. D. Tiers
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Patent number: 5147727Abstract: This invention relates to aryloxy polyvinyl ethers having the formula ##STR1## wherein R is a radical having from 2 to 20 carbon atoms and is selected from the group of alkylene, alkyleneoxy alkylene, polyalkyleneoxy alkylene, arylene, alkarylene, alkarylalkylene and aralkylene; X is oxygen or sulfur; A is branched or linear alkylene having from 1 to 20 carbon atoms; B is halo or lower alkyl; n has a value of from 1 to 6 and p has a value of from 0 to 4. The invention also relates to the preparation and use of said aryloxy divinyl ethers.Type: GrantFiled: October 7, 1991Date of Patent: September 15, 1992Assignee: ISP Investments Inc.Inventors: Kou-Chang Liu, Fulvio J. Vara, James A. Dougherty
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Patent number: 5105014Abstract: The present invention relates to an improved method of forming vicinal diamines. The method according to the present invention has the advantage of being highly stereoselective, capable of forming a wide variety of diamines including racemic and enantiomeric forms, and employing readily available starting and reaction materials.In particular the present invention relates to a method of forming vicinal diamines from a bis-imine precursor using nucleophilic additions of organometallic reagents.Type: GrantFiled: August 6, 1991Date of Patent: April 14, 1992Assignee: Mallinckrodt Medical, Inc.Inventor: William L. Neumann
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Patent number: 5100767Abstract: The present invention provides a photopolymerizable composition useful as a liquid photoimageable solder mask comprising (a) a reaction product obtained by reacting epoxy resin A containing at least two terminated epoxy groups with 0.8 to 1.2 mol, per 1 epoxy equivalent of epoxy resin A, of an .alpha.,.beta.-unsaturated carboxylic acid and then reacting same with 0.2 to 1.0 mol, per 1 epoxy equivalent of epoxy resin A, of polybasic acid anhydride, (b) diluent, (c) sensitizer, (d) epoxy resin B consisting of tris (2,3-epoxypropyl) isocyanurate whose melting point is 130.degree. C. or less, and (e) an epoxy resin curing agent represented by the general formula [I:] ##STR1## wherein R is --H, halogen, --NH.sub.2, --SH, aromatic hydrocarbon, a C.sub.1 -C.sub.4 alkyl group or NHR' (R' is a C.sub.1 -C.sub.4 alkyl group having --CN or NH.sub.2 C.dbd.NH).Type: GrantFiled: December 19, 1989Date of Patent: March 31, 1992Assignee: Tamura Kaken Co., Ltd.Inventors: Makoto Yanagawa, Shinji Santo
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Patent number: 5096938Abstract: Radiation-curable catalysts are obtainable by reactingA) 1 equivalent of a dihydric to hexahydric oxyalkylated C.sub.2 -C.sub.10 -alcohol withB) from 0.05 to 1 equivalent of a dibasic to tetrabasic C.sub.3 -C.sub.36 -carboxylic acid or its anhydride andC) from 0.1 to 1.5 equivalents of acrylic acid and/or methacrylic acidand reacting the excess carboxyl groups with an equivalent amount of epoxide compound, and are used in radiation-curable coating materials.Type: GrantFiled: April 3, 1990Date of Patent: March 17, 1992Assignee: BASF AktiengesellschaftInventors: Erich Beck, Wolfram Weiss, Horst Schmidt
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Patent number: 5086088Abstract: The invention relates to a pressure-sensitive thermosetting adhesive comprising from about 30% to about 80% by weight of a photopolymerizable prepolymeric or monomeric syrup containing an acrylic ester and a polar copolymerizable monomer, from about 20% to about 60% by weight of an epoxy resin or a mixture of epoxy resins containing no photopolymerizable groups, from about 0.5% to about 10% by weight of a heat-activatable hardener for the epoxy resin, from about 0.01% to about 5% of a photoinitiator, and from 0% to about 5% of a photocrosslinking agent. In a preferred embodiment, imidazoles and thermally expandable thermoplastic microspheres are utilized in the inventive adhesive formulation.Type: GrantFiled: December 21, 1990Date of Patent: February 4, 1992Assignee: Minnesota Mining and Manufacturing CompanyInventors: Shuichi Kitano, Kiyoshi Ogata, Shinobu Sato
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Patent number: 5082874Abstract: This invention relates to aryloxy polyvinyl ethers having the formula ##STR1## wherein R is a radical having from 2 to 20 carbon atoms and is selected from the group of alkylene, alkyleneoxy alkylene, polyalkyleneoxy alkylene, arylene, alkarylene, alkarylalkylene and aralkylene; X is oxygen or sulfur; A is branched or linear alkylene having from 1 to 20 carbon atoms; B is halo or lower alkyl; n has a value of from 1 to 6 and p has a value of from 0 to 4. The invention also relates to the preparation and use of said aryloxy divinyl ethers.Type: GrantFiled: February 6, 1990Date of Patent: January 21, 1992Assignee: ISP Investments Inc.Inventors: Kou-Chang Liu, Fulvio J. Vara, James A. Dougherty
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Patent number: 5073476Abstract: Iron (II)-aromatic compound complexes mixed with electron acceptors as an oxidizing agent are suitable initiators for the polymerization by irradiation of organic material which can be polymerized by cations and/or free radicals. The composition composed of the polymerizable material and of the initiator mixture is suitable for the production of protective coatings and can be used as a photographic recording material.Type: GrantFiled: May 10, 1984Date of Patent: December 17, 1991Assignee: Ciba-Geigy CorporationInventors: Kurt Meier, Giuliano Eugster, Franz Schwarzenbach, Hans Zweifel
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Patent number: 5068261Abstract: The fluorine-containing epoxy(meth)acrylate resin of the invention is represented by the following general formula (I). ##STR1## wherein R.sub.f is selected from the group consisting of --.phi.--C(CF.sub.3).sub.2 --.phi.-- ##STR2## --C(CF.sub.3).sub.2 --.phi.'--C(CF.sub.3).sub.2 -- ##STR3## and --CH.sub.2 (CF.sub.2).sub.6 CH.sub.2 --; n is zero or a positive integer; and X is hydrogen or methyl group.The resin of the invention may be prepared by reacting a diglycidyl ether of a fluorine-containing hydrocarbon (R.sub.f) with acrylic acid or methacrylic acid. Further provided is an adhesive composition comprising the aforementioned fluorine-containing epoxy(meth)acrylate resin and a photo polymerization initiator, which can be cured at room temperature within a short time by irradiation with an UV ray to form a cured product having a refractive index n.sub.d.sup.20 ranging from 1.434 to 1.532.Type: GrantFiled: April 3, 1989Date of Patent: November 26, 1991Assignee: Nippon Telegraph and Telephone CorporationInventors: Tohru Maruno, Shigeki Ishibashi, Kouzaburou Nakamura
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Patent number: 5055357Abstract: This invention realtes to a radiation curable cross linkable composition containing (a) from about 0.1 to about 5 wt. % of an initiator containing at least 25% cationic initiator, (b) from about 0 to about 60 wt. % of a polymerizable vinyl ether, expoxide, vinyloxy alkyl urethane or acrylate and (c) from about 35 to about 99.9 wt. % of a polyfunctional alkenyl ether having the formulaA[(CH.sub.2 O).sub.m (Z).sub.r CH.dbd.CHR].sub.nwherein A is a carbon atom, --OCH.dbd.CHR or [C.sub.1 to C.sub.10 alkyl].sub.4-n ; R is C.sub.1 to C.sub.6 alkyl; Z is C.sub.2 to C.sub.8 alkyleneoxy; r has a value of from 0 to 6; m has a value of from 0 to 1 and at least one of r and m has a positive value; n has a value of from 1 to 4, with the proviso that m is 0 and n is one when A is --OCH.dbd.CHR, n has a value of 2 or 3 when A is [C.sub.1 to C.sub.10 alkyl].sub.4-n and n has a value of 4 when A is carbon.Type: GrantFiled: March 18, 1991Date of Patent: October 8, 1991Assignee: Isp Investments Inc.Inventors: Jeffrey S. Plotkin, James A. Dougherty, Fulvio J. Vara, Paul D. Taylor
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Patent number: 5055378Abstract: A solder resist composition contains a specified partially acrylated and/or methacrylated bisphenol A novolak epoxy resin component, and a specified partially acrylated and/or methacrylated cresol novolak and/or phenol novolak epoxy resin component. The composition further contain a photopolymerization initiator, a thermosetting agent, an inorganic filler, and an organic solvent. The composition may further include a silane or titanate coupling agent.Type: GrantFiled: November 10, 1988Date of Patent: October 8, 1991Assignee: Kabushiki Kaisha ToshibaInventors: Masataka Miyamura, Yusuke Wada, Toshiharu Nakagawa, Yuji Nakaizumi, Kazuhiro Takeda
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Patent number: 5047444Abstract: A curable composition, the cure of which can be monitored optically, comprises at least one of a hydride curable silicone, an ethylenically unsaturated compound, and a cationically polymerizable monomer, and as cure monitor dibenzofulvene or derivatives thereof. The cure monitor is a latent fluorophore which reacts under the cure conditions to form a UV-detectable fluorophore.The invention also provides a method for measuring degree of cure of a polymeric material which can be a coating or an article.Type: GrantFiled: May 31, 1989Date of Patent: September 10, 1991Assignee: Minnesota Mining and Manufacturing CompanyInventors: Robert J. DeVoe, Katherine A. Brown-Wensley, George V. D. Tiers
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Patent number: 5021544Abstract: A water dispersible polyester polymer is described having one or more polyester chains and one or more non-ionic polyoxyalkylene chains in which at least 40% of the repeating oxyalkylene units are oxyethylene units. The polyester polymer has a structure in which one or more of the polyoxyalkylene chains are pendent to at least one of the polyester chains. The poloxyalkylene chains provide the polyester with non-ionic stabilization enabling the polyester to form aqueous dispersions which possess good colloid stability.Type: GrantFiled: November 6, 1989Date of Patent: June 4, 1991Assignee: Imperial Chemical Industries PLCInventors: John C. Padget, David A. Pears
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Patent number: 5015709Abstract: The invention provides a radiation-curable liquid resin for use as a secondary coating of lightwave guides which is a reaction product of (meth)acrylic acid or -acid chloride or isocyanatoalkyl-(meth)acrylate with a 1:2 addition compound of a diepoxide with a mean molecular weight.ltoreq.1000 and a short-chain .alpha.,.omega. -diol with a mean molecular weight.ltoreq.700 or with a 1:2 addition compound of a diepoxide with a mean molecular weight.ltoreq.400 and a monovalent aliphatic alcohol with a mean molecular weight.ltoreq.200, where the diepoxide is an aliphatic-aromatic or aromatic diglycidylether, an aliphatic or cycloaliphatic diepoxide or a silicon-organodiepoxide, and where the short-chain .alpha.,.omega. -diol is an .alpha..omega. -hydroxy-terminated polyoxyalkylene, an .alpha.,.omega. -hydroxy-terminated polyester, an .alpha.,.omega. -hydroxy-terminated polybutadiene, an .alpha.,.omega. -hydroxyterminated organo-functional polysiloxane or an .alpha.,.omega. -alkanediol with a mean molecular weight.Type: GrantFiled: December 19, 1988Date of Patent: May 14, 1991Assignee: Siemens AktiengesellschaftInventors: Siegfried Birkle, Hans-Dieter Feucht, Rainer Kamps, Eva Rissel
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Patent number: 5009982Abstract: A photosetting liquid ink composition developable with a dilute alkaline aqueous solution and comprising (A) a resin curable with an activated energy ray, obtained by the reaction of a saturated or unsaturated polybasic acid anhydride with a product of the reaction of a novolak type epoxy compound and an unsaturated monocarboxylic acid, (B) a photopolymerization initiator, and (C) a diluent can be used for the production of an etching resist or a solder resist in the manufacture of a printed circuit. This composition, when combined with a thermosetting component, produces a photosetting and thermosetting liquid ink composition.Type: GrantFiled: June 6, 1988Date of Patent: April 23, 1991Assignee: Taiyo Ink Manufacturing Co., Ltd.Inventors: Yuichi Kamayachi, Syoji Inagaki
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Patent number: 4994348Abstract: A light-sensitive recording material for the production of intaglio printing plates comprises a photopolymerizable and/or photocrosslinkable material which is soluble or dispersible in a developer liquid and on exposure to actinic light is rendered insoluble or no longer dispersible in this developer liquid and which, at least in a surface zone of the surface of the layer which forms the later surface of the printing plate, contains finely divided abrasive particles whose average particle size is within the range from 0.1 to 6 .mu.m, which have a hardness of >4.0 on the Mohs hardness scale, the surface of the layer which forms the later surface of the printing plate has a peak-to-valley height of <2 .mu.m, and the photocrosslinkable and/or photopolymerizable material contains a reaction product of a cycloaliphatic epoxy with acrylic acid or methacrylic acid.Type: GrantFiled: February 24, 1989Date of Patent: February 19, 1991Assignee: BASF AktiengesellschaftInventors: Eleonore Raabe, Erich Beck
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Patent number: 4987053Abstract: Compounds of the general formula I ##STR1## are described in which Q denotes ##STR2## R denotes alkyl, hydroxyalkyl or aryl, R.sup.1 and R.sup.2 denote H, alkyl or alkoxyalkyl,R.sup.3 denotes H, methyl or ethyl,D.sup.1 and D.sup.2 denote saturated hydrocarbon groups,E denotes alkylene, cycloalkylene, arylene, saturated or unsaturated heteroyls or a group of the formula II ##STR3## a and b denote integers from 1 to 4. c denotes an integer from 1 to 3,m denotes 2, 3 or 4, depending on the valency of Q, andn denotes an integer from 1 to m, where all radicals of the same definition may be identical to or different from one another.The compounds are suitable as polymerizable compounds for photopolymerizable mixtures and are distinguished by ready polymerizability in combination with photoinitiators and long shelf lives in the layer.Type: GrantFiled: November 14, 1988Date of Patent: January 22, 1991Assignee: Hoechst AktiengesellschaftInventors: Joachim Gersdorf, Klaus Rose
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Patent number: 4980428Abstract: This invention relates to epoxy vinyl ethers having the formula: ##STR1## wherein R is a polyvalent linear, branched or cyclic hydrocarbon radical having from 2 to 20 carbon atoms, optionally substituted with alkylenoxy; n has a value of from 1 to 20; p has a value of from 1 to 6; and at least one of Y and Y' is ##STR2## which any remaining Y and Y' can be ##STR3## The invention also relates to the synthesis and uses of the above polyphenyl vinyl ethers.Type: GrantFiled: February 16, 1990Date of Patent: December 25, 1990Assignee: GAF Chemicals CorporationInventors: Kou-Chang Liu, Fulvio J. Vara, James A. Dougherty
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Patent number: 4980430Abstract: This invention relates to epoxy vinyl ethers having the formula: ##STR1## where R is a polyvalent linear, branched or cyclic hydrocarbon radical having from 2 to 20 carbon atoms, optionally substituted with alkyleneoxy; A is branched or linear C.sub.1 to C.sub.4 alkylene; B is halogen or lower alkyl; m has a value of from 0 to 4; n has a value of from 0 to 20; p has a value of from 1 to 5; and T is ##STR2## when p is one, and is ##STR3## or a mixture of ##STR4## and ##STR5## when p is greater than one.Type: GrantFiled: February 16, 1990Date of Patent: December 25, 1990Assignee: GAF Chemicals CorporationInventors: Kou-Chang Liu, Fulvio J. Vara, James A. Dougherty
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Patent number: 4975471Abstract: A photo-curable epoxy resin type composition which comprises (a) an epoxy resin, (b) at least one compound selected from the group consisting of (i) a compound having a group, other than an imido group, which is represented by the formula --CONH and (ii) an aromatic amine, (c) an organic metal compound, where said metal is selected from the group consisting of titanium, vanadium, chromium, manganese, iron, cobalt, nickel, copper, zinc, aluminum and zirconium; and (d) an organic silicon compound having at least one group selected from the group consisting of a peroxysilyl group and an o-nitrobenzyloxy group capable of forming a silanol group by irradiation with light. The photo-curable epoxy resin type composition according to this invention is capable of readily curing by light (ultraviolet ray in particular) and also capable of heat curing at a temperature of 150.degree. C.Type: GrantFiled: August 29, 1988Date of Patent: December 4, 1990Assignee: Kabushiki Kaisha ToshibaInventors: Shuzi Hayase, Shuichi Suzuki, Moriyasu Wada
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Patent number: 4970135Abstract: Disclosed is a flame-retardant liquid photosensitive resin composition consisting essentially of(a) a (meth)acrylate obtained by the reaction of a compound having two or more epoxy groups in the molecule with (meth)acryalic acid and a dibasic acid or its anhydride, the (meth)acrylate having an average acid value of 4 to 150 and a number average molecular weight of 300 to 5,000;(b) a monomer having at least one (meth)acryloxyloxy group and containing not less than 20% by weight of bromine;(c) a monomer having two or more (meth)acryloxyloxy groups in the molecule;(d) a monomer having one (meth)acryloyloxy group in the molecule;(e) at least one inorganic filler; and(f) at least one photopolymerization catalyst selected from the group consisting of photo-initiators and photosensitizers,wherein the content of bromine in the total composition is in the range of 0.5 to 28% by weight.Type: GrantFiled: September 25, 1989Date of Patent: November 13, 1990Assignee: Mitsubishi Rayon Co., Ltd.Inventors: Kenji Kushi, Ken-ichi Inukai
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Patent number: 4942112Abstract: Solid photopolymerizable compositions and photosensitive elements are provided that are useful in preparing optical elements, and especially holograms. The composition contains a polymeric binder, a liquid ethylenically unsaturated monomer, and a photoinitiator system. Typical compositions have a refractive index modulation of at least 0.005 when measured per the specified test.Type: GrantFiled: January 15, 1988Date of Patent: July 17, 1990Assignee: E. I. Du Pont de Nemours and CompanyInventors: Bruce M. Monroe, William K. Smothers
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Patent number: 4933259Abstract: A composition useful as an alkaline developable liquid photoimageable solder resist ink comprising a photocurable resin, a photopolymerization initiator, a reactive diluent, a solvent and optionally, a thermosetting material as main components wherein the photocurable resin comprises a reaction product of: (A) an epoxy vinyl ester resin obtained by reacting a cresol novolak epoxy resin and an unsaturated monobasic acid, (B) a polybasic acid anhydride and (C) an alkyl ketene dimer, wherein the hydroxyl value of the photocurable resin is not more than 10 carbons. Coating films formed from the subject composition have excellent adhesion, heat resistance, moisture insulation resistance and alkaline developable properties.Type: GrantFiled: August 24, 1988Date of Patent: June 12, 1990Assignee: Arakawa Chemical Industries, Ltd.Inventors: Machio Chihara, Mitsukazu Funahashi
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Patent number: 4925773Abstract: A solder resist ink composition is disclosed which contains a photo-curable resin obtained by causing an unsaturated monocarboxylic acid to react with a cresolnovolak- or phenolnovolak-type epoxy resin, and causing a polybasic carboxylic anhydride to react with the resultant reaction product, a photo-curable resin obtained by causing an unsaturated monocarboxylic acid to react with a bisphenol A novolak- or cycloaliphatic oxirane novolak-type opoxy resin, and causing a polybasic carboxylic anhydride to react with the resultant reaction product, at least one photo-polymerizable compound selected from photo-polymerizable monomers, a photo-polymerization initiator, an organic solvent, and an inorganic filler. Also disclosed are two other solder resist ink compositions each having a different photo-curable component.Type: GrantFiled: December 18, 1987Date of Patent: May 15, 1990Assignee: Kabushiki Kaisha ToshibaInventors: Masataka Miyamura, Yuusuke Wada, Kazuhiro Takeda, Yuji Nakaizumi, Teiji Kohara
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Patent number: 4902726Abstract: There is disclosed a photosensitive resin composition solution for formation of a printed wiring board permanent mask to be coated on a substrate to be coated according to the curtain flow coating method or the roll coating method, which comprises (A) an oligomer having at least one epoxy group and at least one polymerizable vinyl group in the side chain, (B) a photopolymerization initiator, (C) an epoxy resin curing agent, (D) a filler and (E) a solvent, characterized in that (1) the solvent (E) contains 10 to 20% by weight of at least one low boiling point solvent selected from the group consisting of methanol, ethanol, methyl ethyl ketone, acetone and ethyl acetate based on the total amount of the solvent, and (2) the composition solution has a viscosity at 25.degree. C. of 100 mPas or more and 200 mPas or less.Type: GrantFiled: May 11, 1988Date of Patent: February 20, 1990Assignees: Hitachi Chemical Company, Ltd., Ibiden Co., Ltd.Inventors: Nobuyuki Hayashi, Katsushige Tsukada, Tadashi Fujii, Katsunori Tsuchiya
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Patent number: 4888269Abstract: A resin composition for use in a solder resist ink, said composition comprising as essential ingredients(A) an epoxy vinyl ester resin solution obtained by dissolving (A-a) an epoxy vinyl ester resin obtained by reacting a phenol novolak-type epoxy resin and/or a cresol novolak-type epoxy resin with 0.40 to 0.85 mol, per epoxy group of the epoxy resin, of an unsaturated monobasic acid in (A-b) an organic and/or (A-c) at least one photopolymerizable polyfunctional vinyl monomer selected from the group consisting trifunctional or higher polyoxyalkylene glycol poly(meth)acrylates, poly(meth)acrylates of polyoxyalkyl isocyanurates and poly(meth)acrylates of acetal compounds,(B) a photopolymerization initiator, and(C) a curing agent of an amino group and/or imino group-containing epoxy resin.Type: GrantFiled: August 11, 1988Date of Patent: December 19, 1989Assignees: Dainippon Ink & Chemicals, Inc., Asahi Chemical Research Laboratory, Ltd.Inventors: Yoneji Sato, Masato Hoshino, Seiichi Kitazawa, Tadashi Yasuda
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Patent number: 4876322Abstract: Linear fluorooligomers having at least two reactive end groups per polymer molecule are incorporated into radiation sensitive polymer systems which have improved continuous temperature resistance and low dielectric constant. The polymer systems can be applied as lacquers. Preferably perfluorated poly-ethers and perfluorated alkanes are used as starting compounds. The polymeric product is usable as a coating for the production of printed multi-layer wirings and economises on through-bores and additional copper intermediate layers. A further field of application exists in the field of integrated semiconductor circuits in VLSI-technology for the production of negative photo-resists.Type: GrantFiled: September 4, 1987Date of Patent: October 24, 1989Assignee: Siemens AktiengesselschaftInventors: Klaus Budde, Friedrich Koch, Ferdinand Quella
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Patent number: 4869995Abstract: A positive type photosensitive resinous composition which is specifically useful in a photoresist for printed circuit board, integrated circuit board and the like and in a lithographic plate is provided.The resinous composition is characterized by comprising a resin having in its side chains or at the end portions of main chain at least one iminosulfonate group of the formula: ##STR1## in which R.sub.1 and R.sub.2 each is selected from hydrogen atom, an alkyl, an acyl, a phenyl, a naphthyl, an anthryl and a benzyl group, or R.sub.1 and R.sub.2 may, taken together, form an alicyclic ring, the iminosulfonate content being 1.5.times.10.sup.-4 to 2.5.times.10.sup.-3 equivalent/g and the resin being free from glycidyl group or the like which may cause polymerization in the presence of sulfonic acid.Type: GrantFiled: May 27, 1988Date of Patent: September 26, 1989Assignee: Nippon Paint Co., Ltd.Inventors: Masamitsu Shirai, Masahiro Tsunooka, Makoto Tanaka, Kanji Nishijima, Katsukiyo Ishikawa
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Patent number: 4855333Abstract: A high density dimensionally stable encapsulated wire circuit board and a method of making such a board is described. A photo-curable adhesive having a unique combination of rheological properties is utilized to bond insulated wires to a substrate. The unique combination of rheological properties of the adhesive used in the encapsulated wire circuit boards of this invention include a specified range of values for the Storage Shear Modulus and specified range of values for the Loss Angle ratio.A new photo-curable adhesive having these properties and a method of obtaining such an adhesive are also described.Type: GrantFiled: April 6, 1987Date of Patent: August 8, 1989Assignee: International Business Machines Corp.Inventors: William J. Rudik, George P. Schmitt, John F. Shipley
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Patent number: 4849320Abstract: The invention provides a process for the production of an image which comprises(i) applying to a substrate a layer of a liquid composition comprising(A) a cationically polymerizable residue(B) a radiation-activated polymerization initator for (A)(C) a radiation-curable residue that is different from (A) and optionally(D) a radiation activated initiator for the cure of (C),(ii) subjecting the composition to actinic radiation having a wavelength at which initiator (B) is activated but at which the residue (C) and/or initiator (D) is not substantially activated, followed by heating, if necessary, so that (A) is polymerized and the layer of liquid composition is solidified, but remains curable,(iii) subjecting the solidified layer in a predetermined pattern to actinic radiation having a wavelength that is different from that of the radiation used in stage (ii) and at which the radiation-curable residue (C) and/or the initiator (D) is activated, such that in the exposed areas (C) is substantially cured, and(iv) reType: GrantFiled: April 30, 1987Date of Patent: July 18, 1989Assignee: Ciba-Geigy CorporationInventors: Edward Irving, Christopher P. Banks
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Patent number: 4831063Abstract: A photocurable composition comprising (1) an epoxy compound having at least one epoxy group and at least one unsaturated double bond in the same molecule; (2) a metal compound present in an amount ranging from 0.001 to 10 wt. %, based on the epoxy compound; and (3) a silicon compound which is capable of forming a silanol group when irradiated with light and which is present in an amount ranging from 0.1 to 20 wt. %, based on the epoxy compound, is characterized by a particularly rapid curing rate.Type: GrantFiled: February 24, 1987Date of Patent: May 16, 1989Assignee: Kabushiki Kaisha ToshibaInventors: Shuichi Suzuki, Moriyasu Wada, Shuzi Hayase
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Patent number: 4816496Abstract: Disclosed are photocurable compositions which comprise(A) a compound having at least one epoxy group and at least one photocurable unsaturated ethylenic double bond within the same molecule;(B) an organometallic compound and(C) a silicon compound capable of generating silanol group by irradiation of light, or comprise(A) a compound having at least one epoxy group and at least one photocurable unsaturated ethylenic double bond within the same molecule;(E) an epoxy compound;(F) an organic phosphorus compound; and(G) a photosensitizer.The compositions of the present invention have excellent film characteristics such as good adhesion property, light resistance, heat resistance and weathering resistance.Type: GrantFiled: May 30, 1985Date of Patent: March 28, 1989Assignee: Kabushiki Kaisha ToshibaInventors: Moriyasu Wada, Shuichi Suzuki, Yuusuke Wada, Shuzi Hayase, Yukihiro Mikogami
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Patent number: 4776992Abstract: Coated, reinforced composites are prepared by a process in which(i) a liquid composition comprising a photocurable residue and a residue having at least one epoxide group or phenolic hydroxyl group is applied to the surface of a mould,(ii) the composition is exposed to actinic radiation until it solidifies,(iii) reinforcement and a thermosettable composition are applied to the solidified layer, this composition containing an epoxide resin or a phenolic resin,(iv) the assembly is heated to form a cured moulding, and(v) the moulding is removed from the mould.Type: GrantFiled: July 25, 1986Date of Patent: October 11, 1988Assignee: Ciba-Geigy CorporationInventors: Edward Irving, Terence J. Smith
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Patent number: 4774267Abstract: Dental restorative compositions comprising a polymerizable polyfunctional prepolymer type methacrylate having the following chemical formulas: ##STR1## and a filler material, are disclosed. The prepolymer monomers and polymer formed are also taught.Type: GrantFiled: August 4, 1987Date of Patent: September 27, 1988Assignee: IPCO Corp.Inventor: Yuri Weintraub
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Patent number: 4758608Abstract: Ultraviolet curable terpolymers of trioxane, from at least 65 weight percent to about 75 weight percent of 1,3-dioxolane and from about 2 weight percent to about 20 weight percent of a monoethylenically unsaturated aliphatic diol formal having at least 4 carbon atoms in its main chain, e.g., 4,7-dehydro- 1,3-dioxepin, which are non-crystalline at room temperature or above are disclosed. These terpolymers, when admixed with a multifunctional crosslinking monomer, e.g., a multifunctional acrylate such as 1,6-hexanediol diacrylate, and a photosensitizer, e.g., a benzoin compound such as benzoin isobutyl ether, can be cured to an insoluble, non-tacky, rubbery state using UV radiation. The thus-cured polymeric materials form useful crosslinked films, and when cryogenically ground to a suitable small particle size can be blended with conventionally prepared crystalline oxymethylene homo-, co- and terpolymers to improve the latters' impact properties.Type: GrantFiled: September 14, 1987Date of Patent: July 19, 1988Assignee: Hoechst Celanese CorporationInventors: George L. Collins, Paul Zema, William M. Pleban
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Thermally stable, irradiation cross-linkable polymer systems based on bisphenols and epichlorohydrin
Patent number: 4735891Abstract: For shortening the exposure time of radiation-sensitive epoxy resin lacquers based on condensates of bisphenols and epichlorohydrin and for increasing their thermal stability, the number of reactive groups in each polymer repeating unit is increased by incorporating there into at least two hydroxyl groups and preferably five hydroxymethylene groups. When a composition of such a polyhydroxylated condensate is reacted with cinnamic acid chloride or the like, the resulting light sensitive condensate is utilizable as a coating in the manufacture of printed multilayer wirings. Intermediate tempering, drilling and additional protective films are eliminated. Such a condensate can also be employed in the field of integrated semiconductor circuits in VLSI technology where lacquer structures are produced.Type: GrantFiled: June 27, 1985Date of Patent: April 5, 1988Assignee: Siemens AktiengesellschaftInventors: Klaus Budde, Oskar Nuyken -
Patent number: 4732843Abstract: Linear fluorooligomers having at least two reactive end groups per polymer molecule are incorporated into radiation sensitive polymer systems which have improved continuous temperature resistance and low dielectric constant. The polymer systems can be applied as lacquers. Preferably perfluorated poly-ethers and perfluorated alkanes are used as starting compounds. The polymeric product is usable as a coating for the production of printed multi-layer wirings and economises on through-bores and additional copper intermeidate layers. A further field of application exists in the field of integrated semiconductor ciruits in VLSI-technology for the production of negative photo-resists.Type: GrantFiled: August 5, 1985Date of Patent: March 22, 1988Assignee: Siemens AktiengesellschaftInventors: Klaus Budde, Friedrich Koch, Ferdinand Quella
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Patent number: 4725524Abstract: In dry film resists possessing a solid photopolymerizable resist layer, which is applied on a temporary base and can be developed with aqueous, in particular aqueous alkaline, media, and, if required, a cover sheet on the resist layer, the said resist layer is built from a homogeneous mixture of (a) not less than 40% by weight of one or more oligomers which contain free carboxyl groups and more than two acryloyl and/or methacryloyl groups and are soluble or dispersible in aqueous alkaline solutions, (b) from 1 to 35% by weight of one or more film-forming compatible polymers which are soluble in aqueous media, (c) from 1 to 30% by weight of one or more compatible photopolymerizable monomers, (d) from 0.001 to 10% by weight of one or more photoinitiators and (e) from 0 to 30% by weight of further additives and/or assistants. Resist images are produced on a substrate by a process employing photopolymerizable resist layers of the type stated above.Type: GrantFiled: December 18, 1985Date of Patent: February 16, 1988Assignee: BASF AktiengesellschaftInventors: Albert Elzer, Gunnar Schornick, Axel Sanner
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Patent number: 4714751Abstract: Oligomeric resins are crosslinkable by polymerization, soluble or dispersible in aqueous alkaline solutions, preferably contain more than 2 (meth)acryloyl groups and free carboxyl groups and are prepared by a special process. Photosensitive, photopolymerizable and crosslinkable recording materials for optical information fixing are based on these oligomeric resins, and lithographic printing plates are produced by a process in which the novel photosensitive recording materials are used.Type: GrantFiled: December 18, 1985Date of Patent: December 22, 1987Assignee: BASF AktiengesellschaftInventors: Gunnar Schornick, Albert Elzer, Reiner Hofmann
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Patent number: 4687806Abstract: This invention relates to the addition of lithium bromide to a polymeric material to reduce the viscosity of the polymeric material. This invention finds particular use in the reduction of the viscosity of radiation curable compositions, such as polyacrylates.Type: GrantFiled: November 15, 1985Date of Patent: August 18, 1987Assignee: Interez, Inc.Inventors: William J. Morris, deceased, Richard R. Kemmerer, Byron K. Christmas
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Patent number: 4657983Abstract: Radiation curable copolymers useful in coating compositions are prepared by reacting part of the glycidyl groups of a glycidyl acrylate copolymer with acrylic or methacrylic acid followed by esterifying the remaining glycidyl groups with phosphoric acid.Type: GrantFiled: December 5, 1984Date of Patent: April 14, 1987Assignee: Interez, Inc.Inventor: Ronald J. Skiscim