With Solid Polymer Derived Solely From Ethylenic Monomers Patents (Class 522/95)
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Patent number: 4761435Abstract: Ultraviolet-curable ethylenically unsaturated liquid coating composition are disclosed which consist essentially of:1--polyethylenically unsaturated material in which the ethylenically unsaturated groups are polymerizable groups which are not (meth)acrylate groups;2--a polyamine resin, preferably a polytertiary amine resin; and3--an aryl ketone photosensitizer.Type: GrantFiled: October 3, 1986Date of Patent: August 2, 1988Assignee: DeSoto, Inc.Inventors: Edward J. Murphy, Ronald S. Conti
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Patent number: 4761136Abstract: A dental impression material which comprises a pre-polymer formed by reacting a polyol or combination polyester polyol with a diisocyanate, and then with a hydroxyacrylate or hydroxymethacrylate; along with a metal catalyst, plasticizer, photosensitizer, reducing agent, filler and other additives. The essential characteristics of the polymer portion that makes the system work are that it is a long-chain aliphatic polyester-polyurethane molecule, which when endcapped with hydroxy arcylate moieties, is photo-polymerizable to yield a tear-resistant, highly flexible, medium-durometer elastomer, suitable for use as a dental impression material.Type: GrantFiled: August 6, 1987Date of Patent: August 2, 1988Assignee: Kerr Manufacturing CompanyInventors: Narayanan Madhavan, Carole L. Groh, Robert L. Probst
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Patent number: 4740532Abstract: A dielectric coating composition that is screen printable and radiation curable is disclosed. The composition is composed of from about 10 percent to about 50 percent of an unsaturated thiolene prepolymer system, from about 0 percent to about 35 percent of an acrylated prepolymer system, from about 10 percent to about 40 percent of at least one crosslinking diluent monomer, from about 4 percent to about 18 percent of at least one plasticizer and from about 3 percent to about 12 percent of at least one nonshrinking monomer. The cured coating is sufficiently compliant at normal temperatures to avoid cracking upon flexure of thermal expansion of the substrate.Type: GrantFiled: December 9, 1986Date of Patent: April 26, 1988Assignee: AMP IncorporatedInventors: Clifton C. May, Jr., Steven G. Wentink
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Patent number: 4705740Abstract: A layer comprised of a radiation-polymerizable mixture containing (a) a first compound capable of undergoing free radical polymerization, the first compound containing at least two terminal ethylenically unsaturated groups and having a boiling point above 100.degree. C. under atmospheric pressure, (b) a second compound capable of initiating the polymerization of the first compound when exposed to actinic radiation, and (c) a water-insoluble copolymer which is soluble in aqueous alkaline solutions and which comprises (c1) an .alpha..beta.-unsaturated aliphatic carboxylic acid and (c2) an alkyl methacrylate having at least 4 carbon atoms in the alkyl group, wherein the copolymer has a mean molecular weight in the range from about 50,000 to 200,000 possesses high flexiblity and resilience in both unexposed and exposed states. The mixture is particularly suitable for use as dry resist material for the tenting technique in printed circuit board production.Type: GrantFiled: July 11, 1985Date of Patent: November 10, 1987Assignee: Hoechst AktiengesellschaftInventors: Ulrich Geissler, Klaus Albrecht
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Patent number: 4702997Abstract: A photopolymerizable laminate comprising a photopolymerizable layer and a support layer, said photopolymerizable layer containing;(1) 5 to 95% by weight, based on the total weight of the photopolymerizable layer, of a binder comprising a vinyl polymer or a vinyl copolymer,(2) 95 to 5% by weight, based on the total weight of the photopolymerizable layer, of a monomeric component containing at least 50% by weight of at least one compound selected from the group consisting of the photopolymerizable unsaturated compounds represented by the formulae (A), (B) and (C) shown below and having a value of molecular weight/number of double bonds contained of 1000 or less, and(3) 0.01 to 30% by weight, based on the total weight of the photopolymerizable layer, of a photopolymerization initiator.Type: GrantFiled: February 6, 1986Date of Patent: October 27, 1987Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Hideo Ai, Akihiko Ideda, Jiro Sato
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Patent number: 4698373Abstract: Compositions hardenable by exposure to heat or electromagnetic radiation are provided by dissolving together to form a blend from about 0% to about 50% by weight of an uncrosslinked polymer, from about 2% to about 30% of a polymerizable monomer, from about 10% to about 70% of a crosslinked polymer in the form of discrete particles having average diameters of from 0.001 micron to about 500 microns and being swollen in said solution and from about 20% to about 70% of a crosslinking agent for said monomer. Such compositions exhibit superior chemical and physical characteristics when hardened and are suitable in a wide variety of applications as construction media. Such compositions are especially suitable in the production of prosthetic dental appliances, such as, for example, prosthetic teeth. It is believed that the hardening of such compositions as, for example, during the preparation of dental appliances forms a polymer system known as an interpenetrating polymer network.Type: GrantFiled: April 30, 1984Date of Patent: October 6, 1987Assignee: Dentsply Research & Development Corp.Inventors: Louis Tateosian, Frederick D. Roemer
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Patent number: 4692396Abstract: A photopolymerizable resin composition for aqueous-developing type dry film resists which comprises(A) 40 to 85% by weight of a binder resin comprising a copolymer of methyl methacrylate, methyl acrylate and methacrylic acid,(B) 15 to 60% by weight of a crosslinkable monomer having at least two ethylenically unsaturated groups in the molecule, and(C) 0.5 to 10% by weight, based on the total amount of the above components (A) and (B), of a photoinitiator.Type: GrantFiled: April 3, 1985Date of Patent: September 8, 1987Inventor: Hiroyuki Uchida
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Patent number: 4691045Abstract: A hydroxyl group-containing (meth)acrylate oligomer represented by the general formula I: ##STR1## wherein two R.sup.1 's independently stand for hydrogen atom or methyl group, two Z's independently stand for a divalent organic group of 2 to 20 carbon atoms, and p stands for an integer of the value of 1 to 100, and urethane, carboxyl and hydroxyl modified prepolymer thereof.Type: GrantFiled: December 5, 1985Date of Patent: September 1, 1987Assignee: Nippon Shokubai Kagaku Co., Ltd.Inventors: Shuzo Fukuchi, Shigeru Yamaguchi
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Patent number: 4688053Abstract: A liquid jet recording head having a liquid passage communicated to a liquid discharging outlet provided on a substrate surface is obtained, said passage being formed by subjecting a layer of a resin composition curable with an active energy ray to a predetermined pattern exposure with the use of said active energy ray to thereby form a cured region of said resin composition and removing the uncured region from said layer, said resin composition comprising:(i) a linear polymer having a glass transition temperature of 50.degree. C. or higher and a weight average molecular weight of about 3.0.times.10.sup.4 or higher;(ii) a monomer having an ethylenically unsaturated bond;(iii) an epoxy resin comprising at least one compound having one or more epoxy groups in the molecule; and(iv) a polymerization initiator capable of generating a Lewis acid by irradiation with an active energy ray.Type: GrantFiled: July 8, 1986Date of Patent: August 18, 1987Assignee: Canon Kabushiki KaishaInventors: Hiromichi Noguchi, Tadayoshi Inamoto, Megumi Munakata
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Patent number: 4688055Abstract: A liquid jet recording head has a liquid passage communicated to the discharging outlet of the liquid which is formed with a resin composition cured with an active energy ray. The resin composition to be cured comprises (i) a heat-crosslinkable linear copolymer containing 5-30 mol % of a monomer of formula I and 5-50 mol % of a monomer of formula II ##STR1## and (ii) a monomer having an ethylenically unsaturated bond.Type: GrantFiled: July 3, 1986Date of Patent: August 18, 1987Assignee: Canon Kabushiki KaishaInventors: Hiromichi Noguchi, Tadayoshi Inamoto, Megumi Munakata
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Patent number: 4686171Abstract: Disclosed is an aqueous developable, photopolymerizable composition having increased flexibility and reduced cold flow comprising a unique mixture of a siliceous material and a plasticizer in combination with known photopolymerizable monomers, polymeric binders, thermal polymerization inhibitors, and photoinitiators.Type: GrantFiled: February 14, 1986Date of Patent: August 11, 1987Assignee: Hercules IncorporatedInventors: Charles C. Fifield, Richard T. Mayes, Marilyn Tate, Daniel F. Varnell
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Patent number: 4654233Abstract: A coating composition is provided. The coating composition is a curable blend of ethylenically unsaturated polyester and ethylenically unsaturated thermoplastic polymers. The composition is capable of providing a thermoplastic, soluble, sandable, intermediate-stage coating and, when cured, a final stage coating which is unaffected by acetone placed on the final stage coating for two hours at 22.degree. C., has a percent haze value of 15% or less, and is unaffected when subjected to a Wet Print Test.Type: GrantFiled: November 21, 1984Date of Patent: March 31, 1987Assignee: Minnesota Mining and Manufacturing CompanyInventors: Richard J. Grant, Gilbert C. Johnson, Heather V. Landin
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Patent number: 4652604Abstract: This invention relates to a radiation polymerizable composition for use in a photographic element such as a lithographic printing plate comprising in admixture(a) a binder resin having the general formula--A--B--C--wherein a plurality of each of components A, B and C occur in ordered or random sequence in the resin and wherein A is present in said resin at about 5% to about 20% by weight and comprises groups of the formula ##STR1## B is present in said resin at about 4% to about 30% by weight and comprises groups of the formula ##STR2## and C is present in said resin at about 50% to about 91% by weight and comprises acetal groups consisting of groups of the formulae ##STR3## where R is lower alkyl or hydrogen, and wherein said group I is present in component C from about 75% to about 85%, group II is present in component C from about 3% to about 5%; and group III is present in component C from about 10% to about 22%.Type: GrantFiled: August 2, 1985Date of Patent: March 24, 1987Assignee: American Hoechst CorporationInventors: John E. Walls, Carlos Tellechea, Major S. Dhillon
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Patent number: 4649062Abstract: Vehicles for ultraviolet radiation-curable ceramic enamels comprise (a) acrylate- or methacrylate-modified oligomers; (b) acrylate or methacrylate monomers, the functionality of (a) and (b) being selected to provide desired film and firing characteristics; (c) a combination of photoinitiators to provide a balance of surface and through cure; and an inhibitor to enhance shelf life. Printing media comprising pigmented frits and the vehicles are described, as are methods for their application to heat-resistant substrates, especially glass.Type: GrantFiled: April 25, 1985Date of Patent: March 10, 1987Assignee: Ciba-Geigy CorporationInventors: Raymond S. Kosiorek, Leslie R. Gatechair
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Patent number: 4643963Abstract: For the production of printing plates, in particular lithographic printing plates by exposing a photopolymerizable recording material imagewise to actinic light and then effecting development with an aqueous alkaline developer, it is proposed to use photopolymerizable recording materials possessing a photopolymerizable copying layer (L) applied on a dimensionally stable base, where, in addition to containing ethylenically unsaturated photopolymerizable low molecular weight compounds, one or more photoinitiators, dyes and/or pigments, and, if required, further additives and/or assistants, the said copying layer (L) also contains, as a binder, one or more oligomeric and/or relatively high molecular weight copolymers which are soluble or dispersible in aqueous alkaline media and are based on cyclic dienes, in particular unsubstituted or substituted cyclopentadiene or unsubstituted or substituted di- or tricyclopentadiene.Type: GrantFiled: October 31, 1984Date of Patent: February 17, 1987Assignee: BASF AktiengesellschaftInventors: Heinrich Hartmann, Gerhard Hoffmann, Hellmut Buensch, Reiner Hofmann
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Patent number: 4634562Abstract: A shapable and photogellable liquid or fluid polyvinyl chloride composition comprising a blend of polyvinyl chloride with sufficient plasticizer and about 13 to 50 parts per hundred of a photopolymerizable polymer to give a liquid or fluid composition. Preferably said composition may contain a photoinitiator and a polyvinyl chloride stabilizer.Type: GrantFiled: September 8, 1981Date of Patent: January 6, 1987Assignee: The Goodyear Tire & Rubber CompanyInventor: Raymond E. Downey
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Patent number: 4629679Abstract: A photopolymerizable resin composition is described which comprises, (a) 40 to 85 wt. %, based on the composition, of a thermoplastic polymer binder, (b) 15 to 60 wt. %, based on the composition, of a cross-linkable monomer having at least one ethylenically unsaturation, (c) 0.5 to 10 wt. %, based on the total of the binder (a) and the monomer (b), of a photopolymerization initiator, and (d) 0.005 to 1 wt. %, based on the total of the binder (a) and the monomer (b), of a tetrazole compound of the formula: ##STR1## wherein R.sub.1 is H, halogen, methyl, ethyl, phenyl, carboxyl, amino, dimethylamino, diethylamino, methoxy, ethoxy, mercapto or sulfonic acid; and R.sub.2 is H, methyl, ethyl, phenyl, amino or mercapto. The photopolymerization resin composition exhibits an enhanced adhesion to a metal surface, and is useful as a photoresist for fabrication of a printed circuit board.Type: GrantFiled: February 25, 1986Date of Patent: December 16, 1986Assignee: Mitsubishi Rayon Company Ltd.Inventors: Hiroyuki Uchida, Jun Nakauchi
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Patent number: 4629680Abstract: A photopolymerizable composition is described, comprising an addition polymerizable unsaturated compound having at least two ethylenically unsaturated double bonds in the molecule, a photopolymerzation initiator, and a binder, said binder being a copolymer composed of at least one recurring unit of group (A), at least one recurring unit of group (B), and at least can recurring unit of group (C), and having a weight average molecular weight of 5,000 to 5,000,000, wherein(A) is a methacrylate or benzyl methacrylate unit having a glass transition point of the homopolymer of higher than 50.degree. C. and having an alkyl group having from 3 to 10 carbon atoms,(B) is an acrylate unit having a glass transition point of the homopolymer of lower than 110.degree. C. and having an alkyl group having from 1 to 6 carbon atoms, and(C) is an .alpha.,.beta.Type: GrantFiled: January 28, 1985Date of Patent: December 16, 1986Assignee: Fuji Photo Film Co., Ltd.Inventors: Masayuki Iwasaki, Minoru Maeda, Fumiaki Shinozaki, Kazuo Maemoto
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Patent number: 4600649Abstract: Ultraviolet-curable, liquid coating compositions are disclosed which are resistant to abrasion and which are strongly adherent to basic plastic surfaces. These compositions comprise one or more polyacrylates or polymethacrylates, preferably including from 70% to 85% of trimethylol propane triacrylate, from 5% to 15% of a carboxylic acid which contains acrylic or methacrylic unsaturation, preferably acrylic acid itself, and photoinitiators (which are preferably ketonic and which desirably comprise a substituted acetophenone and benzophenone) are used to render the composition sensitive to ultraviolet light. The polyacrylate component preferably includes from 1% to 12% of a diacrylate or dimethacrylate of a diglycidyl ether of a bisphenol in which the molecular weight of the diglycidyl ether is less than about 600. The above proportions are based on the total weight of polymerizable material. The composition preferably also includes 0.5% to 2.Type: GrantFiled: October 22, 1984Date of Patent: July 15, 1986Assignee: DeSoto, Inc.Inventor: A. Frank Leo
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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: 4576976Abstract: Disclosed is a process for the photopolymerization of vinyl compounds and of photopolymerizable materials containing vinyl compounds and products produced thereby which are especially useful for dental materials. The process utilizes at least one photosensitizer of the formula ##STR1## wherein X is selected from the group consisting of CO, C(R.sup.1)(R.sup.2) and C(R.sup.3)(OR.sup.4); wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4 are each selected from the group consisting of hydrogen and a hydrocarbon radical;n is 0 or 1; andA is selected from hydrocarbon radicals which may be substituted and which may be bonded together with the proviso that when n is 1 and X is C(R.sup.1)(R.sup.2), and when n is 0, A is an aromatic radical; andat least one reducing agent of formula (I) or (II) ##STR2## wherein Y is selected from oxygen, sulfur or the group NR.sup.1 where R.sup.Type: GrantFiled: March 7, 1984Date of Patent: March 18, 1986Assignee: Kulzer & Co., GmbHInventor: Roland Schaefer