At Least Two Specified Rate-affecting Materials Containing Keto Group Not Part Of A Ring; Or Contains A Nonspecified Photoinitiator Or Photosensitizer And Specified Ketone Containing Material Wherein The Keto Group Is Not Part Of A Ring Patents (Class 522/8)
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Patent number: 5300536Abstract: The present invention relates to a catalytic composition for photopolymerization, which comprises an alpha-diketone and a hydrazone or a silane compound which has a silicon atom carrying a hydrogen, and also relates to a photopolymerizable composition which comprises a vinyl compound capable of radical polymerization and the above catalytic composition. The catalytic composition is markedly improved in photopolymerization activity and the photopolymerizable composition uniformly cures.Type: GrantFiled: September 28, 1992Date of Patent: April 5, 1994Assignee: Toagosei Chemical Industry Co., Ltd.Inventors: Shin Takahashi, Yoshiaki Fujimoto
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Composition of ultraviolet curing antifogging agent and process for forming antifogging coating film
Patent number: 5244935Abstract: An ultraviolet curing antifogging agent is disclosed. The composition includes block copolymer (a) having a hydrophilic polymer segment (a1) and a hydrophobic polymer segment (a2). A polar solvent (c) is provided in which the hydrophilic polymer segment (a1) can easily be dissolved while the hydrophobic polymer segment (a2) can not. It further includes a photopolymerizable compound (b), and a photopolymerization initiator (d). The block copolymer (a) contains at least one hydrophilic monomer selected from the group of: a (meth) acrylamide compound represented by the general formula: CH.sub.2 .dbd.CR.sub.1 CONR.sub.2 R.sub.3 ; a cyclic (meth)acrylamide compound represented by the general formula ##STR1## and a hydroxyalkyl (meth)acrylate. Further, the hydrophilic polymer segment (a1) is formed by a radically polymerizable monomer having a functional group such as glycidyl group.Type: GrantFiled: July 31, 1992Date of Patent: September 14, 1993Assignee: Nippon Oil and Fats Co., Ltd.Inventors: Yoshihiro Oshibe, Yasuhiro Yamamoto, Hiroshi Ohmura, Keiji Kumazawa -
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: 5180756Abstract: Agents which are curable by ultraviolet radiation are based on a binder formulation of (1) from 99.0 to 20% by weight of a copolymer, (2) from 1.0 to 80% by weight of monoolefinically unsaturated compounds and (3) from 0.0 to 20% by weight of polyolefinically unsaturated compounds. The agents contain copolymers (1) which are obtainable by subjecting a mixture of (A) from 80 to 99.9% by weight of olefinically unsaturated monomers, (B) from 0 to 10% by weight of a copolymerizable olefinically unsaturated photoinitiator and (C) from 0 to 10% by weight of a polymerization-regulating photoinitiator to free radical polymerization, the sum of (B) and (C) being not less than 0.1% by weight and the stated percentages by weight being based on the sum of the weights of (A)+(B)+(C).Type: GrantFiled: April 6, 1990Date of Patent: January 19, 1993Assignee: BASF AktiengesellschaftInventors: Gerd Rehmer, Andreas Boettcher
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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: 5071888Abstract: Photopolymerizable prepolymer compositions are provided comprising an unsaturated compound having at least one ethylenic double bond that is photopolymerizable to form a polymer, and a photoinitiator having one of the formulae: ##STR1##Type: GrantFiled: July 8, 1985Date of Patent: December 10, 1991Assignee: Asahi Denka Kogyo K.K.Inventor: Naohiro Kubota
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Patent number: 5043361Abstract: A combined chemical-/light-polymerization type composition for dental restoration consists of a formulation A composed main of a. an ethylenically polymerizable unsaturated compound, b. a photo-polymerization initiator and c. a reducing agent, and a formulation B composed mainly of d. a filler and e. an organic peroxide. The formulations A and B are separately packaged and designed to be mixed for use.Type: GrantFiled: June 7, 1990Date of Patent: August 27, 1991Assignee: G-C Dental Industrial CorporationInventors: Takao Kubota, Tetsuro Sakuma, Ryoji Nakazato
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Patent number: 5008300Abstract: A visible light ray-curable monomeric composition for fastening loose teeth, comprising: a filler component consisting of fine, solid particles having an average size of 0.01 to 100 .mu.m and in an amount of 40% to 85% based on the weight of the total weight of the composition; a polyfunctional monomer component consisting of a radical-polymerizable, polyfunctional monomer; a monofunctional monomer consisting of a radical-polymerizable, monofunctional monomer; and a photopolymerization initiator; having a viscosity of 1,000 to 500,000 cps at a temperature of 25.degree. C., and contained in a light-shielded container.Type: GrantFiled: September 11, 1989Date of Patent: April 16, 1991Assignee: Mitsubishi Rayon Company Ltd.Inventors: Takayuki Makino, Nobuhiro Mukai, Hitoshi Ige
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Patent number: 4992547Abstract: The photopolymerizable mixture described contains(A) at least one ethylenically unsaturated photopolymerisable compound,(B) a photoinitiator of the formula I ##STR1## and (C) a photosensitiser from the group of aromatic carbonyl compounds having a triplet energy of 225-310 kJ/mol, for example xanthones, thioxianthones, coumarins, phthalimides, phenones and the like.Ar is phenyl substituted in the 4-position by a substituted amino group, R.sup.1 and R.sup.2 are alkyl, R.sup.3 and R.sup.4 are alkyl or alkoxyalkyl, or R.sup.3 and R.sup.4 together are 3-oxapentamethylene. Said sensitisers (C) raise the activity of said photoinitiators (B) without shortening the shelf life of the mixtures. The photocurable mixtures are used especially as binders for printing inks or paints.Type: GrantFiled: June 14, 1988Date of Patent: February 12, 1991Assignee: Ciba-Geigy CorporationInventors: Godwin Berner, Kurt Meier, Kurt Dietliker, Rinaldo Husler
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Patent number: 4923905Abstract: A light curable dental composition is provided. The composition comprises an ethylenic unsaturated compound and a light polymerization initiator. The light polymerization initiator is a combination of an .alpha.-diketone and a polyperoxy ester containing a benzophenone group and represented by the general formula (I) of: ##STR1## wherein R.sub.1 and R.sub.1 ' represent a tertiary alkyl group or a tertiary aralkyl group and R.sub.2 and R.sub.2 ' represent a hydrogen atom, a tertiary alkoxy group or a tertiary aralkyloxy group.Type: GrantFiled: February 26, 1988Date of Patent: May 8, 1990Assignee: Nippon Oil and Fats Co., Ltd.Inventors: Eiichi Masuhara, Yoshinori Kadoma, Takeo Matsumoto, Takeshi Komai, Eiichi Yamada, Osamu Nakachi, Godo Irukayama
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Patent number: 4916045Abstract: The invention provides a novel photosensitive recording material in the shape of a multilayer element comprising(i) a photopolymerizable or photocrosslinkable relief-forming layer (RL) of a thickness from 0.1 to 6000 .mu.m and(ii) a dimensionally stable support layer.The said relief-forming layer (RL) consists essentially of an ionic polymer, of one or more photoinitiators and, if desired, of one or more photopolymerizable monomers.The said ionic polymer contains(A) from about 45 to 90% by weight, based on the ionic polymer, of a polymer main chain formed from an alkadiene polymer A',(B) from about 6 to about 45% by weight, based on the ionic polymer, of one or mored olefinically unsaturated side radicals having the structure (I), ##STR1## where R.sup.1 and R.sup.2 are different and are each H or a carbon atom of A',R.sup.3 is a polyvalent, straight-chain or branched C.sub.1 -C.sub.Type: GrantFiled: March 30, 1989Date of Patent: April 10, 1990Assignee: BASF AktiengesellschaftInventors: Horst Koch, Wolfgang F. Mueller, Reiner Hofmann, Peter Richter
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Patent number: 4879318Abstract: A method for making a plastic lens and a plastic lens made thereby. The method comprises disposing a liquid monomer or a monomer mixture and a photosensitive initiator into a mold cavity and directing ultraviolet light to act on the lens forming material in the cavity to produce a lens therefrom. The liquid monomer mixture may include one or more of diethylene glycol bis(allyl)-carbonate, bisphenol A diallyl carbonate, 1,6 hexanedioldimethacrylate, trimethylol propane triacrylate, tetraethylene glycol diacrylate, tripropylene glycol diacrylate, tetrahydrofurfurylmethacrylate, tetrahydrofurfuryl acrylate and styrene. The photosensitive initiator may be selected from the group of 2-hydroxy-2-methyl-1- phenyl-propan-1-one and 1-hydroxycyclohexyl phenyl ketone.Type: GrantFiled: November 18, 1988Date of Patent: November 7, 1989Assignee: Ophthalmic Research Group International, Inc.Inventors: N. Thornton Lipscomb, Omar M. Buazza
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Patent number: 4877922Abstract: Disclosed is an easily-dyeable resin composition used in a sublimation type heat-sensitive transfer process. The composition comprises 100 parts by weight of a mixture composed of 40 to 95% by weight of a polyester resin and 5 to 60% of a crosslinking agent curable with active energy rays, and 0.01 to 12 parts by weight of a surface active agent selected from silicon-containing surface active agents and fluorine-containing surface active agents.Type: GrantFiled: March 27, 1989Date of Patent: October 31, 1989Assignee: Mitsubishi Rayon Company, Ltd.Inventors: Isao Sasaki, Kenji Kushi, Nobuyoshi Taguchi
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Patent number: 4835193Abstract: A photopolymerizable epoxy resin composition comprising (a) an epoxy resin and (b) a heteropoly-acid aromatic sulfonium salt or a heteropoly-acid aromatic iodonium salt as a photocuring catalyst exhibits rapid photopolymerization, with the cured product being great in hardness, the corrosive action being weak, and the electrical properties being excellent. The industrial utility of the composition is therefore substantial.Type: GrantFiled: May 7, 1987Date of Patent: May 30, 1989Assignee: Kabushiki Kaisha ToshibaInventors: Shuzi Hayase, Yasunobu Onishi, Shuichi Suzuki, Moriyasu Wada
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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: 4780487Abstract: Radiation curable coating compositions of reduced gloss are obtained by an admixture of (A) about 10 to 90% by weight of a polydiene-based acrylourethane oligomer comprised of the reaction product of a curable lactone modified acrylate or methacrylate and an isocyanate functional urethane and (B) about 10 to 90% by weight of a standard acrylourethane oligomer.Type: GrantFiled: October 22, 1986Date of Patent: October 25, 1988Inventors: Thomas Kurpiewski, Richard E. Heinze
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Patent number: 4771084Abstract: A novel light curing composition for dental restoration comprises (a) a polymerizable compound containing at least one ethylenically unsaturated double-bond, (b) at least one photo-polymerization initiator selected from ketal base compounds defined hereinafter, (c) at least one photo-polymerization initiator selected from benzoin alkyl ether base compounds defined hereinafter, (d) a reducing agent and (e) a filler.Type: GrantFiled: September 11, 1986Date of Patent: September 13, 1988Assignee: G-C Dental Industrial Corp.Inventors: Takao Kubota, Tetsuro Sakuma, Ryoji Nakazato
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Patent number: 4767797Abstract: A linear polymer having a recurring unit represented by the formula (I): ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 each independently is a hydrogen atom, a C.sub.1-10 alkyl group, a C.sub.6-10 cycloalkyl group, an aryl group, or a halogen atom and the ethynyl group is in either meta position or para position to the main polymer chain;and a weight-average molecular weight of 1,000 to 1,000,000. A resin composition consisting essentially of (i) a polymer having a recurring unit represented by the formula (I) or a polymer having a recurring unit represented by the formula (I) and a recurring unit represented by the formula (II): ##STR2## wherein X and Y each independently is a C.sub.6-20 aryl group, a C.sub.1-10 alkyl group, a C.sub.6-10 cycloalkyl group, a silyl group having a C.sub.1-10 alkyl group or a C.sub.Type: GrantFiled: August 25, 1986Date of Patent: August 30, 1988Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Hideo Ai, Yohsuke Koizumi, Naohiro Tsuruta
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Patent number: 4755450Abstract: Spectral sensitizing dyes which sensitize photoinitiators and disperse in aqueous solutions are desirable in photosensitive systems where precise color rendition is important.Type: GrantFiled: April 22, 1986Date of Patent: July 5, 1988Assignee: Minnesota Mining and Manufacturing CompanyInventors: James F. Sanders, David B. Olson
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Patent number: 4755541Abstract: As initiators for the photopolymerisation of ethylenically unsaturated compounds, the use of systems consisting of compounds of benzophenone type of formula I ##STR1## in which R, R' and R.sup.2 are preferably alkyls of 1-4 carbon atoms, R.sup.3 and R.sup.4 are preferably hydrogen and Ar is preferably phenyl, in combination with donors of hydrogen or substances which determine the formation of labile photochemical complexes, such as alcohols, ethers and tertiary amines with hydrogen in the alpha position, and the use for the same purpose of mixtures of 2,4,6-trialkylbenzophenones and benzophenone and particularly of a mixture of 2,4,6-trimethylbenzophenone and benzophenone in a molar ratio of 1.155, which has the advantage of being liquid at temperatures exceeding 10.degree. C. and of possessing photochemical activity superior to that of benzophenone.Type: GrantFiled: July 18, 1986Date of Patent: July 5, 1988Assignee: Fratelli Lamberti SpAInventors: Giuseppe Li Bassi, Luciano Cadona, Carlo Nicora
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Patent number: 4746685Abstract: A light curable dental composition is provided. The composition comprises an ethylenic unsaturated compound and a light polymerization initiator. The light polymerization initiator is selected from a combination of an organic peroxide and a pyrylium salt compound of: ##STR1## Wherein R.sub.1, R.sub.2, and R.sub.3 each represents a hydrogen atom, an alkyl group and the like, X stands for an oxygen or sulfur atom and Y for an anionic functional group; a polyperoxy ester containing a benzophenone group; and a combination the polyperoxy ester and an .alpha.-diketone.Type: GrantFiled: August 23, 1985Date of Patent: May 24, 1988Assignee: Nippon Oil and Fats Co., Ltd.Inventors: Eiichi Masuhara, Yoshinori Kadoma, Takeo Matsumoto, Takeshi Komai, Eiichi Yamada, Osamu Nakachi, Godo Irukayama
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Patent number: 4721734Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is hydrogen, chlorine, phenyl, dialkylamino of 2-4 carbon atoms or alkyl or alkoxy each of up to 18 carbon atoms; R.sub.2 is hydrogen, chlorine, bromine or alkyl or alkoxy each of up to 4 carbon atoms; R.sub.3 and R.sub.4, which can be the same or different, each is hydrogen or alkyl of up to 6 carbon atoms; R.sub.5 is hydrogen or alkyl or alkanoyl each of up to 4 carbon atoms; and R.sub.6 is hydrogen or methyl, with the proviso that not all of R.sub.1 to R.sub.6 simultaneously are hydrogen, are effective photosensitizers, especially for photopolymerization of unsaturated compounds and for hardening of printing dyes.Type: GrantFiled: August 31, 1984Date of Patent: January 26, 1988Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Juergen Gehlhaus, Manfred Kieser
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Patent number: 4694029Abstract: A photopolymerizable composition comprises a polymerizable epoxy-containing material, a polymerizable monomer or monomers containing one or more ##STR1## groups wherein R is H or CH.sub.3, a cationic photoinitiator, a radical-type photoinitiator and an alcohol accelerator.Type: GrantFiled: April 9, 1985Date of Patent: September 15, 1987Assignee: Cook Paint and Varnish CompanyInventor: John M. Land
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Patent number: 4666951Abstract: There is disclosed a photo-curable epoxy resin type composition comprising an epoxy resin, an aluminum compound, a silicon compound having a peroxysilyl group and a photosensitizer.The compositions of the present invention can suitably be used for wide varieties of electrical applications.Type: GrantFiled: March 19, 1984Date of Patent: May 19, 1987Assignee: Tokyo Shibaura Denki Kabushiki KaishaInventors: Yasunobu Onishi, Shuzi Havase, Shuichi Suzuki, Moriyasu Wada
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Patent number: 4661434Abstract: A photopolymerizable composition comprising (A) an addition-polymerizable unsaturated compound having two or more ethylenically unsaturated double bonds and (B) a ternary photopolymerization initiator system, comprising a combination of a 4,4'-bis(dialkylamino)benzophenone represented by the following general formula (I), a carbonyl compound represented by the following general formula (IIa) or (IIb), and a compound having a group represented by the following general formula (III): ##STR1## wherein each R, which may be the same or different, represents an alkyl group, a cycloalkyl group or a hydroxyalkyl group, or may be bonded to another R substituent of the same nitrogen atom to form a tetramethylene group, a pentamethylene group or an oxybisethylene group; ##STR2## wherein X represents a single bond, an oxygen atom, a sulfur atom, a substituted or unsubstituted nitrogen atom or a carbonyl group, R.sup.1 and R.sup.Type: GrantFiled: August 16, 1984Date of Patent: April 28, 1987Assignee: Fuji Photo Film Co., Ltd.Inventors: Masayuki Iwasaki, Minoru Maeda, Fumiaki Shinozaki
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Patent number: 4649082Abstract: Disclosed is an ungelled radiation curable resin which is a reaction product of (a) a polyfunctional hydroxyl-containing carboxylic acid having a molecular weight less than or equal to 1,000 and having a total functionality of equal to or greater than 3; (b) an organic hydroxyl-functional compound; and (c) an alpha, beta-ethylenically unsaturated carboxylic acid. Also disclosed is a radiation curable composition containing the radiation curable resin in combination with a polymer having a glass transition temperature equal to or higher than minus 17 degrees Celsius selected from an acrylic polymer and a polyester polymer.The radiation curable resins are particularly useful for coatings over non-metallic substrates such as ABS plastics, etc., having an adherent, thin film of metal deposited by vacuum metallizing, sputtering, electroless deposition, electroplating, and the like.Type: GrantFiled: March 7, 1985Date of Patent: March 10, 1987Assignee: PPG Industries, Inc.Inventor: Charles B. Friedlander
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Patent number: 4623676Abstract: A radiation-curable composition suitable for use as a protective coating for a photographic element comprises a polymerizable acrylic compound, a polymerizable epoxy-functional silane compound, a free-radical photoinitiator capable of initiating polymerization of said acrylic compound, and 0 to 2 percent of the total composition on a weight basis of a cationic photoinitiator capable of initiating polymerization of said epoxy-functional silane compound, said composition containing epoxy functionality only in a silane compound.Type: GrantFiled: January 18, 1985Date of Patent: November 18, 1986Assignee: Minnesota Mining and Manufacturing CompanyInventor: John F. Kistner
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Patent number: 4609612Abstract: There are obtained by mixing together approximately equal parts of 1-benzoylcyclohexanol and benzophenone or a benzophenone derivative liquid mixtures which possess a high activity as photoinitiators for the polymerization of ethylenically unsaturated compounds. The level of activity is higher than that of the individual components taken separately.Type: GrantFiled: October 4, 1985Date of Patent: September 2, 1986Assignee: Ciba Geigy CorporationInventors: Godwin Berner, Aloysius H. Manse
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Patent number: 4599155Abstract: There is disclosed a resin composition comprising(A) a spiro ortho ester compound and/or a spiro ortho carbonate compound;(B) an aluminum compound; and(C) a silanol compound or a silicon compound which is capable of generating a silanol group;the amounts of components (B) and (C) being within the range of 0.001 to 10% by weight and 0.1 to 20% by weiht, based on the amount of component (A), respectively.The resin composition of this invention is excellent in volumetric shrinkage performance at curing operation and is good in storability. Therefore, the cured product can be used for a wide variety of industrially valuable applications, such as an ink, a coating, an adhesive, a surface coating, an encapsulation and an electrical insulating material.Type: GrantFiled: September 21, 1984Date of Patent: July 8, 1986Assignee: Kabushiki Kaisha ToshibaInventors: Shuichi Suzuki, Moriyasu Wada, Shuzi Hayase
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Patent number: 4576975Abstract: Michler's ketone analogs and salts thereof, which are photosensitizers in water-soluble photoinitiator systems used to induce polymerization in free-radically-curable, ethylenically-unsaturated materials, are disclosed. The Michler's ketone analogs have the formula: ##STR1## wherein each R is an alkyl group of 1 to 8 carbon atoms,R.sup.1 is an alkylene group having 1 to 8 carbon atoms,Z is R.sup.1 COOH or R.sup.1 H, andn is an integer having a value of 1 or 2.The photoinitiator systems are useful in imaging systems, and additionally contain a free radical initiator compound selected from iodonium salts, biimidazoles, trialkylphosphites, alkyl peroxides, benzyl halides, alkyl nitrates, and the benzophenones other than (a).Type: GrantFiled: December 18, 1984Date of Patent: March 18, 1986Assignee: Minnesota Mining and Manufacturing CompanyInventor: Laurence W. Reilly, Jr.
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Patent number: 4571377Abstract: Disclosed is a photopolymerizable vehicle and method for the selective photopolymerization of said vehicle by the application of a plurality of different selected wavelengths of energy wherein any single wavelength of energy is inadequate for effecting said photopolymerization. The method comprises sequentially applying a plurality of different selected wavelengths of energy to said vehicle whereby polymerization is effected at the intersection of said wavelengths of energy.Type: GrantFiled: January 23, 1984Date of Patent: February 18, 1986Assignee: Battelle Memorial InstituteInventors: Vincent D. McGinniss, Robert E. Schwerzel