With Solid Polymer Derived Solely From Ethylencally Unsaturated Monomers Patents (Class 522/102)
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Patent number: 6426373Abstract: Among other things, a photopolymerizing one-component dental material is prepared, containing: 1) 80-10 weight-% of at least one polyfunctional urethane methacrylate and/or at least one polyfunctional urethane acrylate, 2) 10-30 weight-% of at least one polyfunctional acrylate resin, 3) 10-30 weight-% of at least one reactive thinner, 4) 0-20 weight-% of bis-GMA and/or at least one ethoxylated bisphenol-A-dimethacrylate, 5) 0-10 weight-% of at least one filler, 6) 0-1 weight-% of at least one photoinitiator, and. 7) 0-1 weight-% of at least one color pigment.Type: GrantFiled: August 12, 1999Date of Patent: July 30, 2002Assignee: Heraeus Kulzer GmbH & Co. KGInventors: Frank Stange, Albert Erdrich, Novica Savic, Teresa Puchalska
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Patent number: 6350791Abstract: The invention relates to a thermosettable adhesive comprising a thermosettable polymer component, a thermoformable polymer component, an effective amount of a heat-activatable and/or photoactivatable curing system for curing the thermosettable polymer component, and from 0.5-20 wt. % with respect to the mass of the thermosettable adhesive of one or more hydroxides and/or hydroxyoxides of Al, Mg and/or Zr.Type: GrantFiled: June 27, 2000Date of Patent: February 26, 2002Assignee: 3M Innovative Properties CompanyInventors: Georg Feichtmeier, Peggy S. Willett
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Patent number: 6350403Abstract: The present invention relates to a process for the production of three-dimensional articles by stereolithography using a radiation-curable composition comprising a mixture of at least one cationically polymerizable compound and/or at least one free radical polymerizable compound, at least one filler material and at least one photoinitiator for cationic and/or radical polymerization. An organic viscosity stabilizer material may be brought into contact with the composition to substantially delay or prevent undesirable viscosity increase and subsequently premature polymerization. A filler material is optionally added to the composition in an effective amount to at least delay or prevent a significant increase in viscosity and polymerization. The process is particularly suitable for stabilizing resins in stereolithography baths.Type: GrantFiled: May 31, 2000Date of Patent: February 26, 2002Assignee: Vantico Inc.Inventors: Anastasios P. Melisaris, Stephen D. Hanna, Thomas H. Pang
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Patent number: 6348517Abstract: A method of preparing a sterile article is disclosed. A polymer having a halogen-containing repeating unit is prepared that contains about 0.Type: GrantFiled: September 1, 2000Date of Patent: February 19, 2002Assignee: Oxy Services, Inc.Inventors: Qi Wang, Sandor Nagy
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Patent number: 6332291Abstract: This invention relates to radiation-curable coating compositions which contain A) compounds having one or more free-radically polymerisable double bonds which additionally contain at least one further functional group reactive for the purposes of an addition and/or condensation reaction, B) compounds having one or more free-radically polymerisable double bonds, which additionally contain at least one further functional group reactive for the purposes of an addition and/or condensation reaction, wherein the additional reactive functional group is complementary to or reactive towards the additional reactive functional groups of component A), C) optionally at least one monomeric, oligomeric and/or polymeric compound having at least one functional group reactive towards the functional groups from component A) or component B) D) one or more photoinitiators as well as E) optionally solvents, water, pigments and/or extenders as well as conventional lacquer additives, wherein component A) and component B) diffeType: GrantFiled: December 17, 1999Date of Patent: December 25, 2001Assignee: Herberts GmbH & Co. KGInventors: Carmen Flosbach, Helmut Löffler, Karin Maag
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Publication number: 20010053437Abstract: A photo curable resin composition, which comprises (A) an acid-modified, vinyl group-containing epoxy resin, (B) an elastomer, (C) a photopolymerization initiator, (D) a diluent and (E) a curing agent, can give a high performance cured film having distinguished heat resistance, humidity-heat resistance, adhesibility, mechanical characteristics and electrical characteristics, and a photosensitive element, which comprises a support and a layer of the photo curable resin composition laid on the support, has distinguished heat resistance, humidity-heat resistance, adhesibility, mechanical characteristics and electrical characteristics.Type: ApplicationFiled: July 3, 2001Publication date: December 20, 2001Inventors: Kuniaki Sato, Hiroaki Hirakura, Toshihiko Ito, Takao Hirayama, Toshizumi Yoshino
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Patent number: 6329442Abstract: A curable composite material composition comprising (A) a polymerizable unsaturated compound, (B) a fiber reinforcing material and/or fiber, and (C) a polymerization initiator comprising an organic boron compound represented by the general formula (1) wherein R1, R2, R3 and R4 each independently represent an alkyl, aryl, allyl, aralkyl, alkenyl, alkynyl, silyl or heterocyclic group, a halogen atom, or a substituted alkyl, substituted aryl, substituted allyl, substituted aralkyl, substituted alkenyl, substituted alkynyl or substituted silyl group, and Z+ represents a cation, and an acidic compound, as well as a curing process for the curable composite material composition which includes irradiating and/or heating the curable composite material composition.Type: GrantFiled: November 9, 2000Date of Patent: December 11, 2001Assignees: Showa Denko K.K., Showa Highpolymer Co., Ltd.Inventors: Shuichi Sugita, Hirotoshi Kamata, Tomio Yamamoto, Kazuo Ohtani, Hidetake Sendai
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Patent number: 6274643Abstract: A curable composition comprising a) a curable epoxy resin, a thermoplastic ethylene-vinyl acetate copolymer resin, and an effective amount of a photocatalyst for the curable epoxy resin, wherein the composition is free from hydrocarbon polyolefins and wherein the sum of a) and b) is 100 weight percent.Type: GrantFiled: July 26, 2000Date of Patent: August 14, 2001Assignee: 3M Innovative Properties CompanyInventors: Naimul Karim, Clayton A. George, Christopher M. Meyer
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Patent number: 6211262Abstract: A corrosion resistant coating for metal surfaces curable with actinic radiation. The blend uses acrylate resin, photoinitiator and a corrosion preventing agent such as a metal surface passivator, overbased calcium sulfonate/calcium carbonate, a barrier pigment, or a combination of two or more of these agents.Type: GrantFiled: April 20, 1999Date of Patent: April 3, 2001Assignee: Spectra Group Limited, Inc.Inventors: Alexandre Mejiritski, Thomas Marino, Violeta Lungu, Dustin Martin, Douglas Neckers
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Patent number: 6207726Abstract: A photocurable prepreg composition which is characterized by easy control of a B stage state of a thermosetting resin such as an unsaturated polyester resin or an epoxy acrylate resin, excellent storage stability, and remarkable curability after being shaped; as well as a production method therefor. A photocurable prepreg composition which contains an unsaturated polyester resin and/or an epoxy acrylate resin; at least two photopolymerization initiators with photosensitivity in different wavelength ranges; and an inorganic or an organic fiber-reinforcing material and/or filler, and which composition is treated with light of a specific wavelength such that at least one photopolymerization initiator and radical-polymerizable unsaturated groups remain partially in said resin; a production method therefor; and formed articles produced therefrom.Type: GrantFiled: February 11, 1999Date of Patent: March 27, 2001Assignees: Showa Denko Kabushiki Kaisha, Showa Highpolymer Co., Ltd.Inventors: Kazuo Ohtani, Tomio Yamamoto, Hidetake Sendai, Shuichi Sugita, Hirotoshi Kamata, Takeo Watanabe
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Patent number: 6194480Abstract: A colored photosensitive composition is composed of a pigment composition, a binder polymer having an acidic group, a multi-functional monomer having at least two ethylenic unsaturated double bonds, and a photopolymerization initiator. The pigment composition is composed of an organic pigment, a dispersant, and an organic solvent. The dispersant is a copolymer of a polymerizable oligomer having an ethylenic unsaturated double bond in its terminal position and one or more monomers at least one of which has a nitrogen-containing group and an ethylenic unsaturated double bond.Type: GrantFiled: April 10, 1998Date of Patent: February 27, 2001Assignee: Fuji Photo Film Co., Ltd.Inventors: Akihiko Takeda, Shinichiro Morimoto, Kousaku Yoshimura
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Patent number: 6194482Abstract: UV-hardenable and thermally hardenable epoxy resins for the underfilling process in electrical and electronic components are provided. A new casting resin component has an increased storage stability at room temperature of at least 6 months and improved characteristics for the underfilling process including faster hardening and lower viscosity. Filler material with a maximum grain size of 20 &mgr;m and a siloxane component are provided in addition to the casting resin formulation.Type: GrantFiled: November 22, 1999Date of Patent: February 27, 2001Assignee: Siemens AktiengesellschaftInventors: Barbara Lehner, Recai Sezi
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Patent number: 6180317Abstract: An improved photoimagable cationically polymerizable epoxy based coating material is provided, that is suitable for use on a variety of substrates including epoxy-glass laminate boards cured with dicyandiamide. The material includes an epoxy resin system consisting essentially of between about 10% and about 80% by weight of a polyol resin which is a condensation product of epichlorohydrin and bisphenol A having a molecular weight of between about 40,000 and 130,000; and between about 35% and 72% by weight of an epoxidized glycidyl ether of a brominated bisphenol A having a softening point of between about 60° C. and about 110° C. and a molecular weight of between about 600 and 2,500. Optionally, a third resin may be added to the resin system. To this resin system is added about 0.Type: GrantFiled: November 18, 1991Date of Patent: January 30, 2001Assignee: International Business Machines CorporationInventors: Robert David Allen, Richard Allen Day, Donald Herman Glatzel, William Dinan Hinsberg, John Richard Mertz, David John Russell, Gregory Michael Wallraff
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Patent number: 6180187Abstract: A method is disclosed for preparing an electronic assembly using a reworkable underfill encapsulant in which the encapsulant is cured in situ from a curable composition comprising one or more mono-functional maleimide compounds, or one or more mono-functional vinyl compounds other than maleimide compounds, or a combination of maleimide and vinyl compounds, a curing initiator and optionally, one or more fillers or adhesion promoters.Type: GrantFiled: December 22, 1999Date of Patent: January 30, 2001Assignee: National Starch and Chemical Investment Holding CorporationInventors: Bodan Ma, Quinn K. Tong, Chaodong Xiao
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Patent number: 6174932Abstract: A UV curable, flexible, paintable composition is disclosed. The disclosed composition has enhanced durability, thick and thin film adhesion, resistance to mold growth and dimensional changes while reducing solvent emissions. The disclosed composition reduces, if not eliminates, runs and drips during the thermal bake cycles which are associated with using conventional compositions in automotive applications.Type: GrantFiled: May 20, 1998Date of Patent: January 16, 2001Assignee: DenoVus LLCInventors: Jeffrey T. Pachl, Donald Taylor, Todd W. Scrivens
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Patent number: 6162842Abstract: This invention discloses a radiation curable coating composition which is comprised of (1) a crosslinked polymeric resin which is comprised of repeat units which are derived from (a) at least one member selected from the group consisting of acrylate monomers and vinyl aromatic monomers and (b) a crosslinking monomer; (2) an acrylate diluting monomer; and (3) a photocatalyst.Type: GrantFiled: May 18, 1999Date of Patent: December 19, 2000Assignee: The Goodyear Tire & Rubber CompanyInventors: Patrick Andre Roger Freche, Franck Constant Emile Duval
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Patent number: 6153302Abstract: A curable composition comprising a) a curable epoxy resin, a thermoplastic ethylene-vinyl acetate copolymer resin, and an effective amount of a photocatalyst for the curable epoxy resin, wherein the composition is free from hydrocarbon polyolefins and wherein the sum of a) and b) is 100 weight percent.Type: GrantFiled: February 29, 2000Date of Patent: November 28, 2000Assignee: 3M Innovative Properties CompanyInventors: Naimul Karim, Clayton A. George, Christopher M. Meyer
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Patent number: 6136384Abstract: A curable composition comprising a) a curable epoxy resin, a thermoplastic ethylene-vinyl acetate copolymer resin, and an effective amount of a photocatalyst for the curable epoxy resin, wherein the composition is free from hydrocarbon polyolefins and wherein the sum of a) and b) is 100 weight percent.Type: GrantFiled: February 29, 2000Date of Patent: October 24, 2000Assignee: 3M Innovative Properties CompanyInventors: Naimul Karim, Clayton A. George, Christopher M. Meyer
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Patent number: 6114405Abstract: A method for preparing a film suitable for use as the light-modulating unit of an SPD light valve, which film comprises a cross-linked polymer matrix having droplets of a liquid light valve suspension distributed in the cross-linked polymer matrix. The light valve suspension comprises particles suspended in a liquid suspending medium. The method comprises admixing a UV cross-linkable liquid oligomer or polymer and the liquid light valve suspension, emulsifying the resulting admixture to form an emulsion of the liquid light valve suspension in the UV cross-linkable liquid oligomer or polymer, and cross-linking the UV cross-linkable liquid oligomer or polymer while the mixture is in the form of a thin layer of the emulsion by exposing the layer to UV radiation or to an electron beam, such that the film is not damaged due to such exposing. The oligomer or polymer and the particles are free of deleterious effects on one another.Type: GrantFiled: October 9, 1997Date of Patent: September 5, 2000Assignee: Research Frontiers IncorporatedInventors: Huifang Zhuang, Steven M. Slovak, Robert L. Saxe
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Patent number: 6114404Abstract: The present invention relates to a radiation curable ink formulation which has a tan .delta. of from about 0.5 to about 1.5. The radiation curable ink formulation includes a pigment, a radiation cross-linkable monomer or oligomer, and a rheology modifier. Flat panel color filters which contain a black radiation curable ink formulation and one or more colored radiation curable ink formulations are also disclosed. At least one of the black and colored radiation curable ink formulations has a tan .delta. of from about 0.5 to about 1.5 and includes a pigment, a radiation cross-linkable monomer or oligomer, and a rheology modifier. Methods for manufacturing these flat panel color filters are also disclosed. The radiation curable ink formulations of the present invention have the advantage of permitting clean doctoring.Type: GrantFiled: March 22, 1999Date of Patent: September 5, 2000Assignee: Corning IncorporatedInventors: John S. Deeken, Ronald E. Johnson, Lung-Ming Wu, Khalil M. Moussa
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Patent number: 6107364Abstract: Described are a polymerizable composition comprising methyl styrene monomer, polymers comprising monomeric units derived from methyl styrene monomers, and optical products comprising these polymers.Type: GrantFiled: May 9, 1997Date of Patent: August 22, 2000Assignee: 3M Innovative Properties CompanyInventors: Bettie C. Fong, David B. Olson
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Patent number: 6057382Abstract: A curable composition comprising a) a curable epoxy resin, a thermoplastic ethylene-vinyl acetate copolymer resin, and an effective amount of a photocatalyst for the curable epoxy resin, wherein the composition is free from hydrocarbon polyolefins and wherein the sum of a) and b) is 100 weight percent.Type: GrantFiled: May 1, 1998Date of Patent: May 2, 2000Assignee: 3M Innovative Properties CompanyInventors: Naimul Karim, Clayton A. George, Christopher M. Meyer
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Patent number: 6051652Abstract: A composition for preparing a reactive hot melt composition comprises (a) a thermoplastic polymer which comprises a polyolefin having an epoxy group, and (b) a radiation polymerizable component containing (b-1) an aliphatic alkyl (meth)acrylate and (b-2) an acrylic compound having a functional group reactive with an epoxy group. A reactive hot melt composition is obtained by polymerizing this composition so as to polymerize the radiation polymerizable component.The reactive hot melt composition which can be easily hot melt coated, crosslinked quickly in the absence of radiation or moisture after bonding adherends, does not form moisture during crosslinking, and has high flowability during hot melting.Type: GrantFiled: April 30, 1998Date of Patent: April 18, 2000Assignee: 3M Innovative Properties CompanyInventors: Kohichiro Kawate, Shigeyoshi Ishii
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Patent number: 6042943Abstract: The invention relates to a radiation curable primary coating composition for coating an optical fiber, composed of a component having a first end and a second end, a saturated aliphatic backbone, and at least one epoxide group at the first end of the component, and at least one reactive functional group at the second end; a mixture of acrylate monomers, composed of a first monomer having one acrylate group, and a second monomer having at least two acrylate groups; and a photoinitiator. The invention further relates to a radiation curable primary coating composition for coating an optical fiber, composed of a component having a first end and a second end, a saturated aliphatic backbone, and at least one epoxide group at the first end of the component, and at least one reactive functional group at the second end; a mixture of acrylate monomers, composed of a first monomer having one vinyl ether group, and a second monomer having at least two vinyl ether groups; and a photoinitiator.Type: GrantFiled: August 6, 1999Date of Patent: March 28, 2000Assignees: Alvin C. Levy & Associates, Inc., Master Adhesives, Inc.Inventor: Alvin C. Levy
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Patent number: 6017640Abstract: Opaquely pigmented or thick filmed powder coatings for heat sensitive substrates, such as wood, wood composites, for example, medium density fiber board, and plastics, that can be fully cured, especially near the substrate, through the incorporation of a dual cure system in the powder comprising a thermal initiator, such as a peroxide, along with a UV initiator. The UV initiator cures the surface, while the thermal initiator cures at the substrate. Surprisingly, virtually no pregelation occurs during the heated melt and flow out step prior to UV curing. Consequently, the hardened film finish formed on the surface exhibits exceptional smoothness which is comparable to that of traditional UV curable powders. The hardened film finish is also fully cured throughout and exhibits exceptional adhesion to the substrate which cannot be achieved with traditional UV curable powders that have been pigmented.Type: GrantFiled: April 23, 1999Date of Patent: January 25, 2000Assignee: Morton International, Inc.Inventors: Jeno Muthiah, Andrew T. Daly, Richard P. Haley, Joseph J. Kozlowski
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Patent number: 5985952Abstract: The invention relates to a radiation curable primary coating composition for coating an optical fiber, composed of a component having a first end and a second end, a saturated aliphatic backbone, and at least one epoxide group at the first end of the component, and at least one reactive functional group at the second end; a mixture of acrylate monomers, composed of a first monomer having one acrylate group, and a second monomer having at least two acrylate groups; and a photoinitiator. The invention further relates to a radiation curable primary coating composition for coating an optical fiber, composed of a component having a first end and a second end, a saturated aliphatic backbone, and at least one epoxide group at the first end of the component, and at least one reactive functional group at the second end; a mixture of acrylate monomers, composed of a first monomer having one vinyl ether group, and a second monomer having at least two vinyl ether groups; and a photoinitiator.Type: GrantFiled: March 23, 1998Date of Patent: November 16, 1999Assignees: Alvin C. Levy & Associates, Inc., Master Adhesives, Inc.Inventor: Alvin C. Levy
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Patent number: 5932626Abstract: Described are optical products comprising a base and an optical layer. The optical layer is prepared from a polymerizable composition comprising an alkyl-substituted brominated phenolic ester(meth)acrylate monomer.Type: GrantFiled: May 9, 1997Date of Patent: August 3, 1999Assignee: Minnesota Mining and Manufacturing CompanyInventors: Bettie C. Fong, David B. Olson
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Patent number: 5919834Abstract: Disclosed are UV-cured heat transfer labels prepared from a mixture containing at least one thermoplastic resin, at least one material for solvating the thermoplastic resin, the solvating material being either a solvent or liquid monomer, and at least one photo-initiable material which initiates curing of the composition.Type: GrantFiled: September 29, 1997Date of Patent: July 6, 1999Assignee: Illinois Tool Works Inc.Inventors: Myron H. Downs, James D. Singelyn, Bruce W. Downs
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Patent number: 5852067Abstract: A near infrared rays-curing putty composition containing (A) a polymerizable ethylenically unsaturated group-containing resin, (B) a polymerizable ethylenically unsaturated compound and (C) a near infrared rays polymerization initiator, said near infrared rays polymerization initiator (C) being a near infrared rays-absorbing cationic dye and a resin powder consisting of gelation polymer fine particles.Type: GrantFiled: November 15, 1996Date of Patent: December 22, 1998Assignees: Showa Denko K. K., Kansai Paint Co., Ltd.Inventors: Hajime Sukejima, Shinji Tomita, Shuichi Sugita, Kazuhiko Ooga
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Patent number: 5849460Abstract: A photosensitive resin composition for use in manufacture of multi-layer circuit boards with connecting holes between layers is disclosed. The resin composition has excellent adhesion with a plating metal, resolution, photo-curing, thermosetting, thermal resistance, and is capable of being developed using an alkaline solution or an aqueous solution containing a non-halogen based organic solvent as the developing solution. The resin composition comprises a photosensitive epoxy resin, a thermosetting epoxy resin, a reactant of a carboxylic acid added to an acrylonitrile-butadiene rubber and an epoxy resin, a photo-polymerization initiator and a thermosetting agent. This reactant facilitates a high density pattern of connecting holes for circuit boards of the layered type.Type: GrantFiled: July 16, 1997Date of Patent: December 15, 1998Assignee: Hitachi, Ltd.Inventors: Yoshinori Kawai, Mineo Kawamoto, Junichi Katagiri, Masanori Nemoto, Akio Takahashi
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Patent number: 5821277Abstract: A thermosetting composition containing a carbonaceous material (1-1) and a thermosetting resin (1-2), the carbonaceous material (1-1) being obtained by reacting by contacting a carbon material (a) with a polymer (b) having in the molecule thereof at least one particular reactive group such as aziridine group, oxazoline group, N-hydroxyalkylamido group, epoxy group, or hydroxyl group, and an alkoxycarbonyl group represented by the formulaR.sup.1 R.sup.2 R.sup.3 C--O--CO-- (1)wherein each of R.sup.1, R.sup.2, and R.sup.3 stands for a hydrogen atom or an organic residue selected from an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 5 to 8 carbon atoms, an alkylcycloalkyl group having 6 to 16 carbon atoms, or an aryl group having 6 to 16 carbon atoms, wherein at least two of R.sup.1, R.sup.2, and R.sup.Type: GrantFiled: November 1, 1996Date of Patent: October 13, 1998Assignees: Nippon Oil Co., Ltd., Dai Nippon Printing Co., Ltd.Inventors: Takayuki Hirayama, Haruyoshi Sato, Yutaka Otsuki, Masayuki Ando
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Patent number: 5800965Abstract: A photopolymerizable composition for a photosensitive lithographic printing plate, comprising (A) addition-polymerizable ethylenically unsaturated bond-containing monomers, (B) a photopolymerization initiator system and (C) a polymer binder having carboxyl groups in its molecule, wherein the addition-polymerizable ethylenically unsaturated bond-containing monomers (A) contain a specific monomer which is a phosphoric acid ester compound (A-1) having at least one (meth)acryloyl group and/or a compound (A-2) of the following formula ##STR1## wherein R.sup.1 is a hydrogen atom or a methyl group, X is a C.sub.1-6 alkylene group which may be branched and may be substituted by halogen, and m is an integer of at least 2, and the polymer binder (C) having carboxyl groups in its molecule, is a compound having at least a part of the carboxyl groups reacted with an alicyclic epoxy group-containing unsaturated compound.Type: GrantFiled: December 26, 1996Date of Patent: September 1, 1998Assignee: Mitsubishi Chemical CorporationInventors: Shigeo Tsuji, Hideaki Okamoto
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Patent number: 5770659Abstract: Processes for making storage-stable epoxy-capped polyetherester resins are disclosed. In one process, a polyetherester resin is first made by inserting a carboxylic acid derivative into a polyether. Reacting the resin with a capping agent gives an intermediate resin with a reduced content of free carboxylic acid groups. Finally, the intermediate resin reacts with an epoxy compound in the presence of a finishing catalyst under conditions effective to give an epoxy-capped resin. The resins have low weight average molecular weights (less than about 8000), narrow molecular weight distributions (less than 6), and low viscosities, making them an excellent choice for low-VOC formulations. The finishing catalyst helps to minimize resin viscosity drift and improves shelf stability. Curing the resins with a vinyl monomer gives thermosets with an excellent balance of physical properties, including excellent water resistance.Type: GrantFiled: November 10, 1997Date of Patent: June 23, 1998Assignee: Arco Chemical Technology, L.P.Inventors: Gangfeng Cai, Daniel M. Trauth, Lau S. Yang
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Patent number: 5696177Abstract: An active energy ray-curable resin composition comprises:(i) a linear polymer having a glass transition temperature at least equal to 50.degree. C. and a weight-average molecular weight of at least about 3.0.times.10.sup.4 ; and(ii) a resin obtained by esterifying, with an unsaturated carboxylic acid, a part of epoxy groups present in an epoxy resin comprising at least one compound having at least two epoxy groups in a molecule.Type: GrantFiled: May 10, 1994Date of Patent: December 9, 1997Assignee: Canon Kabushiki KaishaInventors: Hiromichi Noguchi, Tadayoshi Inamoto, Megumi Munakata
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Patent number: 5658964Abstract: A printing ink for the printing of security documents by the method of engraved steel die printing, having a viscosity of at least 1 Pa.multidot.s at 40.degree. C. under a shear of about 1000 sec.sup.-1, containing a binder matrix, a polymerization initiator for polymerizable matrix components, fillers and pigments, and the usual additives. The binder matrix contains at least one cationically polymerizable compound, modified to bring about the desired rheology of the ink, and the photoinitiator, activable by UV, heat and EB, is an onium salt capable of releasing a Lewis or Bronsted acid.This ink has best and very rapid drying characteristics.Type: GrantFiled: June 6, 1995Date of Patent: August 19, 1997Assignee: SICPA Holding S.A.Inventors: Philippe Amon, Haim Bretler, Anton Bleikolm, Olivier Rozumek, Pierre Degott
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Patent number: 5644004Abstract: A novel and safe ethylenically unsaturated peroxyester composition derived from an ethylenically unsaturated dicarboxylic acid is provided, as well as processes for making and using the composition. The peroxyester composition comprises about 0.04 to about 0.70 mole fraction of a first component compound having a formula I: ##STR1## about 0.32 to about 0.50 mole fraction of a second component compound having a formula II: ##STR2## about 0.04 to about 0.70 mole fraction of a third component compound having a formula III: ##STR3## wherein Q is an unsaturated ethylene divalent radical and R.sup.1 and R.sup.2 are organic substituents. Polymeric-peroxides are prepared via polymerizing the peroxyester compositions. The peroxyester compositions are also used for curing unsaturated polyester resins and for initiating polymerization of ethylenically unsaturated monomers.Type: GrantFiled: January 25, 1995Date of Patent: July 1, 1997Assignee: Elf Atochem North America, Inc.Inventor: Jose Sanchez
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Patent number: 5612444Abstract: A two-step process for making polyetherester resins is disclosed. A low molecular weight polyol reacts with an aromatic dicarboxylic acid in step one to produce a polyester intermediate. In step two, the polyester intermediate reacts with an anhydride or an aliphatic dicarboxylic acid in the presence of an insertion catalyst to produce a polyetherester resin that contains greater than about 10 wt. % of recurring units derived from the aromatic dicarboxylic acid. The polyetheresters are useful for making thermoset resins with excellent mechanical properties and chemical resistance.Type: GrantFiled: March 28, 1995Date of Patent: March 18, 1997Assignee: ARCO Chemical Technology, L.P.Inventors: Gangfeng Cai, Lau S. Yang, Jeffrey A. Klang
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Patent number: 5610205Abstract: A process for making polyetheresters is disclosed. A polyether is reacted with a carboxylic acid in the presence of a strong protic acid or a metal salt of a strong protic acid to promote insertion of the carboxylic acid into polyether carbon-oxygen bonds to produce a polyetherester. The polyetheresters are useful for various applications in the polyurethane and unsaturated polyester industries.Type: GrantFiled: May 14, 1996Date of Patent: March 11, 1997Assignee: ARCO Chemical Technology, L.P.Inventors: Lau S. Yang, Jeffrey A. Klang
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Patent number: 5585221Abstract: An active energy ray-curing resin composition comprises a graft copolymerized polymer and at least one of a monomer having an ethylenically unsaturated bond and a partially esterified epoxy resin.Type: GrantFiled: March 2, 1994Date of Patent: December 17, 1996Assignee: Canon Kabushiki KaishaInventors: Hiromichi Noguchi, Tadayoshi Inamoto, Megumi Munakata
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Patent number: 5578417Abstract: A process is disclosed for producing a liquid jet recording head comprising applying an active energy-curing resin composition onto at least a part of a surface of a first member for forming a wall of the liquid path; exposing the applied active energy-ray-curing resin to an active energy ray selected from the group consisting of an ultraviolet-ray having an intensity of 1 mW/cm.sup.2 to 100 mW/cm.sup.2 and an electron beam having an intensity of 0.5M Rad to 20M Rad; and providing a second member on the exposed active energy-ray-curing resin composition.Type: GrantFiled: March 20, 1995Date of Patent: November 26, 1996Assignee: Canon Kabushiki KaishaInventors: Hiromichi Noguchi, Tadayoshi Inamoto, Megumi Saito
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Patent number: 5578418Abstract: A process is disclosed for producing a liquid jet recording head comprising applying an active energy-curing resin composition onto at least a part of a surface of a first member for forming a wall of the liquid path; exposing the applied active energy-ray-curing resin to an active energy ray selected from the group consisting of an ultraviolet-ray having an intensity of 1 mW/cm.sup.2 to 100 mW/cm.sup.2 and an electron beam having an intensity of 0.5M Rad to 20M Rad; and providing a second member on the exposed active energy-ray-curing resin composition.Type: GrantFiled: March 20, 1995Date of Patent: November 26, 1996Assignee: Canon Kabushiki KaishaInventors: Hiromichi Noguchi, Tadayoshi Inamoto, Megumi Saito
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Patent number: 5569737Abstract: A process for making polyetheresters is disclosed. A polyether is reacted with a carboxylic acid in the presence of a strong protic acid or a metal salt of a strong protic acid to promote insertion of the carboxylic acid into polyether carbon-oxygen bonds to produce a polyetherester. The polyetheresters are useful for various applications in the polyurethane and unsaturated polyester industries.Type: GrantFiled: April 10, 1995Date of Patent: October 29, 1996Assignee: Arco Chemical Technology, L.P.Inventors: Lau S. Yang, Jeffrey A. Klang
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Patent number: 5558975Abstract: A process is disclosed for producing a liquid jet recording head comprising applying an active energy-curing resin composition onto at least a part of a surface of a first member for forming a wall of the liquid path; exposing the applied active energy-ray-curing resin to an active energy ray selected from the group consisting of an ultraviolet-ray having an intensity of 1 mW/cm.sup.2 to 100 mW/cm.sup.2 and an electron beam having an intensity of 0.5M Rad to 20M Rad; and providing a second member on the exposed active energy-ray-curing resin composition.Type: GrantFiled: March 13, 1995Date of Patent: September 24, 1996Assignee: Canon Kabushiki KaishaInventors: Hiromichi Noguchi, Tadayoshi Inamoto, Megumi Saito
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Patent number: 5543266Abstract: An active energy ray-curing resin composition comprises (i) a graft copolymerized polymer, (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 of an active energy ray.Type: GrantFiled: March 13, 1995Date of Patent: August 6, 1996Assignee: Canon Kabushiki KaishaInventors: Hiromichi Noguchi, Tadayoshi Inamoto, Megumi Munakata
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Patent number: 5539064Abstract: A resist ink composition developable with a diluted, alkaline solution, which exhibits high dispersion stability itself, can form a pattern with excellent resolution, even in the case of a low exposure amount, and can produce a cured resist film excellent in solvent resistance for high-performance printed circuits and which comprises an ultraviolet-curable resin obtained by copolymerizing (a) from 5 to 50% by weight of an ethylenically unsaturated monomer of a general formula: ##STR1## wherein R.sub.1 represents a hydrogen atom or a methyl group; R.sub.2 represents a hydrogen atom or an alkyl group; n represent an integer of from 1 to 4, and/or glycerol mono(meth)acrylate, (b) from 10 to 90% by weight or glycidyl (meth)acrylate and (c) from 0 to 80% by weight of other ethylenically unsaturated monomers capable of copolymerizing with these (a) and (b), followed by reacting the resulting copolymer with from 0.7 to 1.Type: GrantFiled: September 12, 1995Date of Patent: July 23, 1996Assignee: Goo Chemical Industries Co., Ltd.Inventors: Soichi Hashimoto, Satoshi Miyayama, Toshiaki Nishimura, Toshikazu Oda
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Patent number: 5484823Abstract: A photopolymerizable adhesive comprises (A) an acrylic resin having groups represented by the formulae: --COOH, --OH and --NHCH.sub.2 OR (wherein R represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms), a number average molecular weight of from 3,000 to 200,000 and a glass transition temperature of at least 70.degree. C., (B) a photopolymerizable oligomer containing at least one member selected from the group consisting of (a) an acrylate or a methacrylate of a novolak epoxy resin, (b) an acrylate or a methacrylate of a bisphenol epoxy resin and (c) an urethane acrylate of aromatic alcohol or cycloaliphatic alcohol, and (C) a photoinitiator capable of discharging radicals with the action of activation energy.Type: GrantFiled: August 29, 1994Date of Patent: January 16, 1996Assignee: Canon Kabushiki KaishaInventors: Hiromichi Noguchi, Naohito Asai, Yuko Suga
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Patent number: 5476752Abstract: An active energy ray-curing resin composition comprises:(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: April 3, 1995Date of Patent: December 19, 1995Assignee: Canon Kabushiki KaishaInventors: Hiromichi Noguchi, Tadayoshi Inamoto, Megumi Munakata
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Patent number: 5436314Abstract: A process for making polyetheresters is disclosed. A polyether is reacted with a carboxylic acid in the presence of a strong protic acid or a metal salt of a strong protic acid to promote insertion of the carboxylic acid into polyether carbon-oxygen bonds to produce a polyetherester. The polyetheresters are useful for various applications in the polyurethane and unsaturated polyester industries.Type: GrantFiled: April 18, 1994Date of Patent: July 25, 1995Assignee: ARCO Chemical Technology, L.P.Inventors: Lau S. Yang, Jeffrey A. Klang
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Patent number: 5436313Abstract: An improved process for making polyetheresters is disclosed. A polyether is reacted with an anhydride in the presence of a strong protic acid or a metal salt of a strong protic acid in an amount effective to promote insertion of the anhydride into carbon-oxygen bonds of the polyether to produce the polyetherester. Polyetheresters made by the process of the invention are useful in a wide variety of applications, particularly in the polyurethane and unsaturated polyester industries.Type: GrantFiled: March 30, 1994Date of Patent: July 25, 1995Assignee: ARCO Chemical Technology, L.P.Inventors: Jeffrey A. Klang, Lau S. Yang
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Patent number: 5420173Abstract: A novel and safe ethylenically unsaturated peroxyester composition derived from an ethylenically unsaturated dicarboxylic acid is provided, as well as processes for making and using the composition. The peroxyester composition comprises about 0.04 to about 0.70 mole fraction of a first component compound having a formula I: ##STR1## about 0.32 to about 0.50 mole fraction of a second component compound having a formula II: ##STR2## about 0.04 to about 0.70 mole fraction of a third component compound having a formula III: ##STR3## wherein Q is an unsaturated ethylene divalent radical and R.sup.1 and R.sup.2 are organic substituents. Polymeric-peroxides are prepared via polymerizing the peroxyester compositions. The peroxyester compositions are also used for curing unsaturated polyester resins and for initiating polymerization of ethylenically unsaturated monomers.Type: GrantFiled: March 30, 1994Date of Patent: May 30, 1995Inventor: Jose Sanchez