Polyurethane Has An Oxygen Other Than As Part Of A Urethane Or Carboxylic Acid Ester Group Patents (Class 522/97)
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Patent number: 6465539Abstract: The invention relates to an elastic coating system with which dry surfaces can be formed by UV curing of constituents containing (meth)acryloyl groups and by subsequent crosslinking of constituents containing NCO groups with constituents containing active hydrogen. The invention also relates to their use of this coating, system for coating, inter alia, components of plastic.Type: GrantFiled: September 11, 2000Date of Patent: October 15, 2002Assignee: Bayer AktiengesellschaftInventors: Jan Weikard, Wolfgang Fischer, Claus Kobusch, Wolfram Küttner
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Publication number: 20020147248Abstract: A radiation-curable coating composition for an optical fiber comprising a reactive functionality-terminated urethane oligomer, wherein said oligomer comprises the reaction product of (i) a semi-crystalline polyol, and (ii) a non-crystalline polyol in the mole ratio of semi-crystalline polyol to non-crystalline polyol of at least about 1:1, (iii) at least one isocyanate, and (iv) an endcapping compound capable of supplying the functionality terminus.Type: ApplicationFiled: December 6, 2001Publication date: October 10, 2002Applicant: DSM N.V.Inventors: Eva I. Montgomery, Jeanette J. Ward, Michael R. Clark
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Patent number: 6458866Abstract: The invention concerns a polyurethane elastomer containing structural units of type (a), in which: the group —O—R1—O—is a macrodiol group with a molecular weight of approximately 500 to 10000, R2 is a bivalent aliphatic, cycloaliphatic and/or aliphatic-cycloaliphatic group; and X is a short-chain olefinically unsaturated group, Y is NH or O, n is an integer from 1 to 10 and m is an integer of at least 4. The invention also concerns a method of preparing this polyurethane elastomer which can be melt-spun to form fibres or melt-extruded to form foils. The fibres or foils can be exposed to energy-rich radiation such that crosslinking of the polyurethane occurs. Fibres according to the invention display superior properties in terms of textile-mechanical properties, in particular good tensile strength, elongation at tear, residual elongation and heat distortion temperature.Type: GrantFiled: May 15, 1998Date of Patent: October 1, 2002Assignee: Rhodia S.A.Inventors: Wilhelm Oppermann, Frank Hermanutz, Peter Hirt, Michael Schweizer, Oliver Oess
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Patent number: 6455607Abstract: A one-part, cured, radiation-curable liquid matrix composition for affixing coated and inked optical fibers in a ribbon configuration which is peelable from the coated and inked fibers without damage to the integrity of itself or the fibers is disclosed. The composition comprises an aliphatic urethane acrylate oligomer; a reactive monomer having one or more acrylate or methacrylate moieties; a release agent; and an optional photoinitiator. Also disclosed are an optical fiber ribbon array prepared therefrom; a process for removing such matrix composition from inked and coated fibers; a process for preparing such ribbon array; and a radiation-curable coating composition generally applicable for coating a substrate.Type: GrantFiled: March 2, 1999Date of Patent: September 24, 2002Assignee: Borden Chemical, Inc.Inventor: Paul J. Shustack
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Patent number: 6440519Abstract: A photocurable resin composition which comprises (A) a urethane (meth)acrylate oligomer obtained by the reaction of (a) at least one polyol compound preferably selected from the group consisting of polyester polyols and polycarbonate polyols, (b) a polyisocyanate compound, and (c) a hydroxyl group-containing (meth)acrylate compound; (B) a (meth)acrylolylphosphate; (C) a multifunctional (meth)acrylate compound; and (D) a photopolymerization initiator and, optionally, (E) an organosilyl-containing mercapto compound. The composition exhibits a fast cure speed, and the cured products obtained from the composition exhibit superior adhesion under high temperature-high humidity conditions and metal corrosion properties.Type: GrantFiled: September 25, 1998Date of Patent: August 27, 2002Assignees: DSM N.V., JSR Corporation, Japan Fine Coatings Co., Ltd.Inventors: Hideaki Takase, Ryoji Furuta, Toshihiko Takahashi, Takashi Ukachi, Yuichi Takehana
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Patent number: 6423809Abstract: The invention provides a polyurethane type polymeric material for coating optical fibers, based on a fluorinated diol with formula I: CnF2n+1—A—CH2OCH2—C (CH2OH)2—R where n is 2 to 20, and A signifies —CH═CH or —CH2CH2—, and R is an alkyl group containing 1 to 4 carbon atoms. The invention also provides a fiber coated with this polymer which has been light-cured, and a fiber drawing method comprising a step of coating the fiber with a material of the invention.Type: GrantFiled: February 12, 2001Date of Patent: July 23, 2002Assignee: AlcatelInventors: Sophie Vanpoulle, Gérard Orcel, Bob J. Overton, Marie-José Lina, Eric Lacroix
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Patent number: 6423472Abstract: Butadiene-polyether prepolymers which can be used in photopolymer resins are prepared by reacting butadiene homopolymer with a stoichiometric excess of isocyanate and then reacting the product with polyether diol. Thereafter the composition is reacted with hydroxyalkyl(meth)acrylate and alkyldialkanolamine. Flexographic printing plates may be prepared using photopolymer resin comprising butadiene-polyether prepolymers.Type: GrantFiled: March 24, 2000Date of Patent: July 23, 2002Assignee: MacDermid Graphic Arts, Inc.Inventors: Ronald James Kumpfmiller, Martin Lewis Carter
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Patent number: 6413698Abstract: A photohardenable resin composition comprising (A) a urethanated acrylic compound represented by formula (I): (A)a—C—(R)4−a wherein R is H or alkyl; a is 3 or 4; and A represents a group of formula (II): wherein D represents —CH2CH2O—, —CH2CH(CH3)O—, —CH2CH2COO— or —(CH2)6COO—; E represents —CH2CH2O—, —CH2CH(CH3)O—, —COCH2CH2O— or —CO(CH2)6O—; G represents a diol or triol residual group; J represents a divalent or trivalent and substituted or unsubstituted hydrocarbon group; L represents —(CH2CH2O)h— (h: integer of 1 to 4), —(CH2CH(CH3)O)j— (j: integer of 1 to 4), or —(CH2CH2O)k—(CH2CH(CH3)O)m— (k, m: integer of 1 to 3 (k+m=2, 3 or 4); b, c, and d are each 0 or 1 (b+c+d=1, 2 or 3); e is 0, 1 or 2; f is 0 or 1 (e+f=1 or 2); and g is 1 or 2, and (B) a radical polymerizable compound at a (A) : (B) rType: GrantFiled: January 6, 2000Date of Patent: July 2, 2002Assignees: Teijin Seiki Co., Ltd., Takemoto Yushi Kabushiki Kaisha, Shin-Nakamura Chemical Co., Ltd.Inventors: Yorikazu Tamura, Tsuneo Hagiwara, Makoto Ohtake, Minoru Shinoda, Toshiharu Suzuki, Tatsuhiko Ozaki, Yasushi Ishihama, Takayuki Nakamura
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Patent number: 6376609Abstract: The present invention relates to a novel photosensitive resin which can be developed in water and which can be used as a photosensitive resin composition. More specifically, the present invention relates to a composition which is useful as a photosensitive soldering resist for printed circuit board.Type: GrantFiled: February 14, 2001Date of Patent: April 23, 2002Assignee: Ajinomoto Co., Inc.Inventors: Shigeo Nakamura, Tadahiko Yokota
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Patent number: 6376571Abstract: A fast curing radiation-curable composition useful as coating compositions for inner and outer primary coatings, inks, ribbons other matrix material coating layers for coating and surrounding optical fibers. The improved radiation-curable compositions, having a propoxylated monomer or oligomer component, demonstrate unexpectedly fast cure speeds while providing strong adhesion characteristics to a variety of substrates and can also be used as a general radiation-curable adhesive or can be adapted for use in the specialized process of digital versatile disk (DVD) production.Type: GrantFiled: March 6, 1998Date of Patent: April 23, 2002Assignee: DSM N.V.Inventors: Chander P. Chawla, Gerry K. Noren
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Patent number: 6350790Abstract: The process of the present invention involves forming a series of radiation-curable compositions having uniformly consistent properties. The process involves forming a pre-composition, measuring an in-situ sample of said pre-composition to determine a property of the cured pre-composition and adding at least one adjusting agent to form a radiation-curable composition and repeating this process to form at least one further radiation-curable composition wherein said property value for each of said radiation-curable composition and said at least one further radiation-curable composition are each within a target value range for said property.Type: GrantFiled: May 12, 2000Date of Patent: February 26, 2002Assignee: DSM N.V.Inventors: Timothy E. Bishop, Paul E. Snowwhite, James R. Petisce, John M. Zimmerman, James R. Turner
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Patent number: 6344495Abstract: There is provided a photo-curable resin composition comprising a urethane-modified acrylic resin represented by structural formula (I) or (II) and a release agent as indispensable components: wherein five R1's each independently represent a hydrogen atom or a methyl group, R2 represents a C1-C16 hydrocarbon group, X and Y each represent a straight-chain or branched alkylene group, and, with the sum of l, m, n, and o being 100, l is an integer of 20 to 90, m is an integer of 0 to 50, n is an integer of 10 to 80, and o is an integer of 0 to 20; and wherein Z represents a group having a bulky cyclic structure, six R1's each independently represent a hydrogen atom or a methyl group, R2 represents a C1-C16 hydrocarbon group, X and Y each represent a straight-chain or branched alkylene group, and, with the sum of l, m, n, o, and p being 100, l is an integer of 20 to 90, m is an integer of 5 to 80, n is an integer of 0 to 50, o+p is an integer of 10 to 80, and p isType: GrantFiled: July 29, 1999Date of Patent: February 5, 2002Assignee: Dai Nippon Printing Co., Ltd.Inventors: Kenji Ueda, Satoshi Shioda, Mikiko Hojo
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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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Patent number: 6329123Abstract: A negative-acting photoimageable composition useful as a primary imaging resist in the manufacture of printed circuit boards comprises an acid-functional binder polymer, a photopolymerizable component, and a photoinitiator chemical system, in which all or a portion of the photopolymerizable component comprises a (meth)acrylate functional urethane oligomer, wherein the (meth)acrylate functionality is separated from the urethane linkage by at least two alkylene oxide groups and at least one ring-opened lactone group for improved flexibility, tenting strength, fine line adhesion, developer scumming, coupled with unexpectedly improved resistance to processing chemicals, such as alkaline developing solutions, acid etching solutions, and acid plating baths, and stripping ability in strong alkaline aqueous stripping solutions.Type: GrantFiled: July 30, 1999Date of Patent: December 11, 2001Assignee: Morton International Inc.Inventors: Daniel E. Lundy, Robert K. Barr, Edward J. Reardon
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Patent number: 6322951Abstract: A negative-acting photoimageable composition useful as a primary imaging resist in the manufacture of printed circuit boards comprises an acid-functional binder polymer, a photopolymerizable component, and a photoinitiator chemical system, in which all or a portion of the photopolymerizable component comprises a (meth)acrylate functional urethane oligomer, wherein the (meth)acrylate functionality is separated from the urethane linkage by at least two alkylene oxide groups and at least one ring-opened lactone group for improved flexibility, tenting strength, fine line adhesion, developer scumming, coupled with unexpectedly improved resistance to processing chemicals, such as alkaline developing solutions, acid etching solutions, and acid plating baths, and stripping ability in strong alkaline aqueous stripping solutions.Type: GrantFiled: December 11, 1998Date of Patent: November 27, 2001Assignee: Norton International, Inc.Inventors: Daniel E. Lundy, Robert K. Barr, Edward J. Reardon
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Patent number: 6323254Abstract: The present invention relates to binders, which can be cured by free-radical polymerization initiated by UV light, and contain a) 10 to 90 parts by wt. of a polymer which contains, in chemically bound form, both ethylenically unsaturated groups and the reaction product of a resin containing abietic acid with not more than 50% of the OH groups of a polyfunctional alcohol having a molecular weight of less than 500, b) 10 to 90 parts by wt. of one or more mono- di-or oligoesters of (meth)acrylic acid having a molecular weight of less than 800 and c) optionally 0.1 to 10 parts by wt. of a photoinitiator component for the free-radical polymerization wherein the weights of a) and b) add up to 100. The present invention also relates to coating compositions containing these binders which are suitable for the production high-gloss coatings.Type: GrantFiled: January 10, 2000Date of Patent: November 27, 2001Assignee: Bayer AktiengesellschaftInventors: Jan Weikard, Wolfgang Fischer, Manfred Müller
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Patent number: 6319653Abstract: A negative-acting photoimageable composition useful as a primary imaging resist in the manufacture of printed circuit boards comprises an acid-functional binder polymer, a photopolymerizable component, and a photoinitiator chemical system, in which all or a portion of the photopolymerizable component comprises a (meth)acrylate functional urethane oligomer, wherein the (meth)acrylate functionality is separated from the urethane linkage by at least two alkylene oxide groups and at least one ring-opened lactone group for improved flexibility, tenting strength, fine line adhesion, developer scumming, coupled with unexpectedly improved resistance to processing chemicals, such as alkaline developing solutions, acid etching solutions, and acid plating baths, and stripping ability in strong alkaline aqueous stripping solutions. The acid-functional binder polymer has a low molecular weight and does not contain styrene, contributing to stripping ability and improved resolution.Type: GrantFiled: August 18, 1999Date of Patent: November 20, 2001Assignee: Morton International Inc.Inventor: Robert Barr
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Patent number: 6316516Abstract: The present invention relates to a composition for coating optical fibers which contains an oligomer capable of being polymerized, a monomer suitable to control the viscosity of the composition, and an adhesion promoter which includes a compound containing a cyclic structure interposed between at least two reactive silanes which are independently an alkoxysilane or a halosilane. Another composition of the present invention includes an oligomer capable of being polymerized, a monomer suitable to control the viscosity of the composition, an adhesion promoter which includes a compound containing a reactive silane group, and a carrier. The present invention also relates to optical fibers and methods of making such optical fibers using the compositions of the present invention.Type: GrantFiled: April 29, 1999Date of Patent: November 13, 2001Assignee: Corning IncorporatedInventors: Ching Kee Chien, Edward J. Fewkes, Eric H. Urruti, Michael J. Winningham
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Publication number: 20010033981Abstract: The present invention provides a photosensitive resin composition which comprises an urethane resin obtained by reacting (A) a carboxyl group-containing polymer having an acid value of 30 mg KOH/g or more and a glass transition temperature of 30° C. or more, (B) a compound having two isocyanate groups in one molecule, (C) a compound having two hydroxyl groups in one molecule and (D) a photopolymerizable unsaturated monomer having one hydroxyl group in one molecule, and a photopolymerization initiator, and a resin plate for flexography using the photosensitive resin composition, whereby the photosensitive resin composition having water developing properties, high in sensitivity and impact resilience, and excellent in water resistance, ink resistance and press life of a hardened portion forming a line pattern area of a printing plate material and the resin plate for flexography prepared by the use of the photosensitive resin composition can be provided.Type: ApplicationFiled: June 5, 2001Publication date: October 25, 2001Applicant: Tokyo Ohka Kogyo Co., Ltd.Inventors: Toshiya Takagi, Koji Kahara, Toshimi Aoyama, Nobuhiro Kobayashi, Masatoshi Yoshida
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Patent number: 6291133Abstract: The present invention provides a photosensitive resin composition which comprises an urethane resin obtained by reacting (A) a carboxyl group-containing polymer having an acid value of 30 mg KOH/g or more and a glass transition temperature of 30° C. or more, (B) a compound having two isocyanate groups in one molecule, (C) a compound having two hydroxyl groups in one molecule and (D) a photopolymerizable unsaturated monomer having one hydroxyl group in one molecule, and a photopolymerization initiator, and a resin plate for flexography using the photosensitive resin composition, whereby the photosensitive resin composition having water developing properties, high in sensitivity and impact resilience, and excellent in water resistance, ink resistance and press life of a hardened portion forming a line pattern area of a printing plate material and the resin plate for flexography prepared by the use of the photosensitive resin composition can be provided.Type: GrantFiled: May 25, 1999Date of Patent: September 18, 2001Assignees: Tokyo Ohka Kogyo Co. Ltd., Nippon Shokubai Co. Ltd.Inventors: Toshiya Takagi, Toshimi Aoyama, Koji Kahara, Nobuhiro Kobayashi, Masatoshi Yoshida
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Publication number: 20010021727Abstract: Radiation-curable compositions are disclosed which, after cure, are substantially non-yellowing. The compositions are particularly tailored for coating and bundling of optical fibers. A first preferred composition is based on a polyether-type of oligomer diluted with reactive diluents. Isocyanurate structures are included in the composition to raise Tg. A second preferred composition is based on fatty oil comprising (meth)acrylate groups and bisphenol A derivatives comprising (meth)acrylate groups. Photoinitiators can be included to increase cure speed. The formulations do not include material amounts of ingredients which tend to cause yellowing or, in theory, extended conjugation in the cured compositions.Type: ApplicationFiled: March 16, 2001Publication date: September 13, 2001Applicant: DSM N.V.Inventor: David Szum
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Patent number: 6268112Abstract: A photosensitive resin composition including a particular acrylic-urethane resin containing a carboxyl group and an acrylic-urethane resin having a particular segment in a combined manner and containing a photo-polymerization initiator achieves superior sensitivity, resolution, chemical resistance to developer, sandblasting resistance, and stability.Type: GrantFiled: December 16, 1998Date of Patent: July 31, 2001Assignee: The Nippon Synthetic Chemical Industry Co., Ltd.Inventor: Hiroaki Satou
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Patent number: 6268111Abstract: An oligomer is provided having tetraacrylate functionality as well as carboxylic acid functionality. The oligomer is useful as a photopolymerizable binder in photoresists for forming printed circuitry. Particular advantages of the oligomer are found in solder mask-forming compositions which must withstand the conditions of nickel/gold plating.Type: GrantFiled: October 20, 1999Date of Patent: July 31, 2001Assignee: Rohm and Haas CompanyInventors: Lincoln Eramo, Jr., Mitchell G. Male, Robert K. Barr, Daniel E. Lundy
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Patent number: 6265476Abstract: Radiation-curable compositions, having high elongation at break and toughness after cure can include the following pre-mixture components: a) a polymer, oligomer or monomer having at least one (meth)acrylate functional group; b) an oligomer or monomer, exclusive of (meth)acrylate functional groups, having an ethylenically unsaturated functional group; and c) an elongation promoter; wherein the composition, after radiation-cure, has an elongation at break of at least about 200%. Glass substrates and optical fibers are coated with the radiation-curable composition. Monofilament fiber or a plurality of fiber filaments, such as sewing thread, are coated with the radiation-curable binder composition, which after cure, demonstrates high elongation at break.Type: GrantFiled: October 4, 1999Date of Patent: July 24, 2001Assignee: DSM N.V.Inventors: Vadim V. Krongauz, Michael G. Sullivan, Stephen C. Lapin, Edward J. Murphy
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Publication number: 20010003031Abstract: There is provided a photocurable resin composition comprising (A) an urethane acrylate having three or four acrylate groups in the molecule, (B) a radical polymerizable compound different from the above urethane acrylate; and (C) a photopolymerization initiator, the weight ratio of the urethane acrylate (A) to the radical polymerizable compound (B) being 80:20 to 10:90; and a production process thereof. The said photocurable resin composition can provide moldings and stereolithographed objects having excellent dimensional accuracy with a small volume shrinkage factor at the time of photo-curing and excellent heat resistance with a high thermal deformation temperature as well as excellent transparency and mechanical properties such as tensile strength.Type: ApplicationFiled: December 15, 2000Publication date: June 7, 2001Applicant: TEIJIN SEIKI CO., LTDInventors: Yorikazu Tamura, Tsuneo Hagiwara
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Publication number: 20010002409Abstract: Described are preferred UV curable coating compositions which are suitable for use as basecoats in the production of lamp reflectors. Also described are reflector devices and methods for making them.Type: ApplicationFiled: November 30, 1998Publication date: May 31, 2001Inventor: RANDALL T. LAKE
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Patent number: 6240230Abstract: Radiation-curable compositions are disclosed which, after cure, are substantially non-yellowing. The compositions are particularly tailored for coating and bundling of optical fibers. A first preferred composition is based on a polyether-type of oligomer diluted with reactive diluents. Isocyanurate structures are included in the composition to raise Tg. A second preferred composition is based on fatty oil comprising (meth)acrylate groups and bisphenol A derivatives comprising (meth)acrylate groups. Photoinitiators can be included to increase cure speed. The formulations do not include material amounts of ingredients which tend to cause yellowing or, in theory, extended conjugation in the cured compositions.Type: GrantFiled: March 6, 1997Date of Patent: May 29, 2001Assignee: DSM N.V.Inventor: David Szum
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Patent number: 6235397Abstract: A printing sheet having a high gloss and an enhanced ink-setting property has an outermost surface coating layer formed on a substrate sheet from an electron beam-cured resin produced from at least one electron beam-curable unsaturated organic compound selected from (A) unsaturated reaction products obtained by first reacting a long chain alkylene (C15 or more) diol compound having a number average molecular weight of 300 to 10,000, with an aromatic, cycloaliphatic or aliphatic polyisocyanate compound and secondly reacting the first reaction product with a (meth)acrylate of a hydroxyl compound.Type: GrantFiled: April 22, 1999Date of Patent: May 22, 2001Assignee: Oji Paper Co., Ltd.Inventors: Yasufumi Nakayama, Masahiro Kamiya, Shinichi Nagasaki
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Patent number: 6221303Abstract: The invention relates to ophthalmic mouldings, especially contact lenses, obtainable by cross-linking a prepolymer that corresponds essentially to formula (1) wherein the variables are as defined in the claims, in the absence or presence of an additional vinyl comonomer.Type: GrantFiled: August 12, 1999Date of Patent: April 24, 2001Assignee: Novartis AGInventor: Bettina Steinmann
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Patent number: 6214522Abstract: A photosensitive resin, process for its use, and printing plates formed thereby are disclosed wherein the photosensitive resin comprises (i) a polyurethane prepolymer which is the reaction product of at least one polyether diol having olefin unsaturation equal to or less than 0.01 meq/gm, at least one diisocyanate, and a hydroxy-functionalized (meth)acrylate, (ii) at least one monomer and (iii) at least one photoinitiator.Type: GrantFiled: August 28, 1998Date of Patent: April 10, 2001Assignee: MacDermid, IncorporatedInventor: Douglas Leach
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Patent number: 6210796Abstract: Adhesive coating film consisting of a) a radiation-cured coat which comprises from 40 to 90% by weight, preferably from 50 to 60% by weight, of urethane acrylate, from 0 to 20% by weight, preferably from 10 to 15% by weight, of polyether acrylate, from 10 to 50% by weight, preferably from 25 to 40% by weight, of reactive diluent, from 0 to 30% by weight of pigments from 0 to 10% by weight, preferably from 2 to 5% by weight, of a carboxy-functional (meth)acrylic esther [sic], from 0 to 10% by weight of other customary coatings fillers, and in the case of curing with UV radiation, from 0 to 10% by weight, preferably from 3 to 6% by weight, of photoinitiator, and b) which carries on one side an adhesive composition which has free NCO groups in the freshly applied adhesive composition, can be plastified thermally, especially under the intended processing conditions, and has a markedly weak surface tack.Type: GrantFiled: May 1, 1998Date of Patent: April 3, 2001Assignee: BASF Coatings AGInventors: Martin Lobert, Wolfgang Kranig, Werner Kluge-Paletta, Michael Kreitz, Stephan Zöllner, Christian Harder, Bodo Szonn
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Patent number: 6200732Abstract: There is provided a photocurable resin composition comprising (A) an urethane acrylate having three or four acrylate groups in the molecule, (B) a radical polymerizable compound different from the above urethane acrylate; and (C) a photopolymerization initiator, the weight ratio of the urethane acrylate (A) to the radical polymerizable compound (B) being 80:20 to 10:90; and a production process thereof. The said photocurable resin composition can provide moldings and stereolithographed objects having excellent dimensional accuracy with a small volume shrinkage factor at the time of photo-curing and excellent heat resistance with a high thermal deformation temperature as well as excellent transparency and mechanical properties such as tensile strength.Type: GrantFiled: April 14, 1997Date of Patent: March 13, 2001Assignee: Teijin Seikei Co., Ltd.Inventors: Yorikazu Tamura, Tsuneo Hagiwara
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Patent number: 6197459Abstract: A photosensitive resin, process for its use, and printing plates formed thereby are disclosed wherein the photosensitive resin comprises (i) a polyurethane prepolymer which is the reaction product of at least one polyether diol having olefin unsaturation equal to or less than 0.01 meq/gm, at least one diisocyanate, and a hydroxy-functionalized (meth) acrylate, (ii) at least one monomer and (iii) at least one photoinitiator.Type: GrantFiled: July 21, 2000Date of Patent: March 6, 2001Assignee: MacDermid, IncorporatedInventor: Douglas Leach
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Patent number: 6191187Abstract: An optical glass fiber coating composition comprising: (A) a urethane (meth)acrylate polymer, (B) a (meth)acrylate compound represented by the following formula (1), go wherein R1 is a hydrogen or a methyl group (C) a reaction diluent, and (D) a polymerization initiator. The composition has superior storage stability over a long period of time and, at a cured state, exhibits excellent UV resistance, heat resistance, yellowing resistance, and oil resistance.Type: GrantFiled: April 11, 1997Date of Patent: February 20, 2001Assignees: DSM N.V., JSR CorporationInventors: Tetsuya Yamamura, Masakatsu Ukon, Zen Komiya, Takashi Ukachi
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Patent number: 6180741Abstract: A liquid curable resin composition exhibiting superior storing stability and suitable for use as a material for optical fiber ribbon matrix, a bundling material, and a material for up-jacketing fibers. The composition contains a first polydimethylsiloxane compound which contains (i) at least two urethane bonds, (ii) an unreactive organic group attached to at least one end of the first polydimethyl-siloxane, and (iii) a (meth)acrylol group attached to at least one end of the first polydimethylsiloxane, and a second polydimethylsiloxane compound which contains (i) at least two urethane bonds and (ii) an unreactive organic group attached to at least one end of the second polydimethylsiloxane, and optionally a third polysiloxane compound which does not contain urethane bonds.Type: GrantFiled: October 7, 1999Date of Patent: January 30, 2001Assignees: DSM N.V., JSR CorporationInventors: Yoshikazu Yamaguchi, Zen Komiya, Takashi Ukachi
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Patent number: 6165408Abstract: The invention relates to moulded ophthalmic articles, especially contact lenses, which are obtainable by cross-linking a prepolymer which is the copolymerization product of (a) at least one polyalkylene glycol of the formula (1): HO--(CH.sub.2 --CH.sub.2 --O).sub.n --(CHY.sub.1 --CHY.sub.2 --O).sub.m --(CHY.sub.3 --CHY.sub.4 --O).sub.p --H or (1'): HO--[(CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.2 --O--)].sub.q --H, (b) at least one polyhydroxy compound selected from the group consisting of (I) a linear or branched aliphatic polyhydroxy compound of the formula (2): R.sub.1 --(OH--).sub.x or a polyether polyol or polyester polyol derived therefrom, and (ii) a cycloaliphatic polyol selected from the group polyhydroxy-C.sub.5 -C.sub.8 -cycloalkane and unsubstituted mono- or disaccharide, (c) at least one di- or polyisocyanate of the formula (3): R.sub.2 --(NCO).sub.Type: GrantFiled: August 4, 1999Date of Patent: December 26, 2000Assignee: Novartis AGInventor: Bettina Steinmann
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Patent number: 6096796Abstract: A photo-curable resin composition capable of providing a three-dimensional object having excellent mechanical strength and high dimensional accuracy when used in a photo-fabrication process. The resin composition is also capable of providing a three-dimensional object with excellent stability in shape and properties in a photo-fabrication process. The photo-curable composition includes:(A) a compound represented by the formula (1) ##STR1## wherein R.sup.1 and R.sup.2 independently represent a hydrogen atom or a methyl group;(B) a compound having a cyclohexene oxide structure;(C) a cationic photo-initiator;(D) an ethylenically unsaturated monomer;(E) a radical photo-initiator; and(F) a polyol having three or more hydroxyl groups.Type: GrantFiled: December 10, 1997Date of Patent: August 1, 2000Assignees: DSM N.V., JSR Corporation, Japan Fine Coatings Co., Ltd.Inventors: Tsuyoshi Watanabe, Tetsuya Yamamura, Akira Takeuchi, Takashi Ukachi
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Patent number: 6087413Abstract: An ultraviolet curable clearcoat composition comprising (exclusive of any solvent present): (a) about 30% to about 90% by weight of an acrylated aliphatic urethane having a molecular weight of about 1200 to 2600 and formed by the reaction of a multifunctional acrylate with a molecular weight of between about 110 and about 500 with an aliphatic urethane based on a polyether and having a molecular weight of about 800 to about 2200; (b) about 15% to about 70% by weight of a multifunctional acrylate having a molecular weight of about 170 to about 1000 and containing at least two polymerizable unsaturated groups per molecule; and (c) a photopolymerization initiator and/or sensitizer. Also described are preferred processes and clearcoated articles involving preferred clearcoat compositions.Type: GrantFiled: April 20, 1995Date of Patent: July 11, 2000Assignee: Red Spot Paint and Varnish Co., Inc.Inventor: Randall T. Lake
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Patent number: 6080483Abstract: Provided is a radiation-curable, glass optical fiber coating composition which when suitably cured exhibits resistance to attack from hydrocarbon gel cable filing material. The composition containsabout 10 to about 90% by weight of a first radiation-curable oligomer;from 0 to about 40% by weight of a reactive diluent;from 0 to about 40% by weight of a photoinitiator;from 0 to about 10% by weight of a pigment; andabout 10 to about 90% by weight of a second radiation-curable oligomer according to the following formula:R.sup.1 -L.sup.1 -C.sup.1 -L.sup.2 -R.sup.2 (1)where:R.sup.1 and R.sup.2, independently, each represent a radiation-curable functional group;L.sup.1 and L.sup.2, independently, each represent an alkyleneoxy chain having from about 2 to about 40 carbon atoms, wherein L.sup.1 and L.sup.2 are linked to C.sup.1 through an oxygen atomC.sup.1 comprises a hydrocarbon having from about 5 to about 40 carbon atoms and containing at least one cyclic group.Type: GrantFiled: July 10, 1997Date of Patent: June 27, 2000Assignee: DSM N.V.Inventors: David M. Szum, Timothy E. Bishop, Steven R. Schmid
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Patent number: 6066436Abstract: Butadiene-polyether prepolymers which can be used in photopolymer resins are prepared by reacting butadiene homopolymer with a stoichiometric excess of isocyanate and then reacting the product with polyether diol. Thereafter the composition is reacted with hydroxyalkyl(meth)acrylate and alkyldialkanolamine. Flexographic printing plates may be prepared using photopolymer resin comprising butadiene-polyether prepolymers.Type: GrantFiled: September 9, 1996Date of Patent: May 23, 2000Assignee: Polyfibron Technologies, Inc.Inventors: Ronald James Kumpfmiller, Martin Lewis Carter
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Patent number: 6057034Abstract: In the coating composition for a optical fiber of the present invention, a polyurethane (meth)acrylate oligomer (A), which is based on a urethane prepolymer having an equivalent ratio of NCO group in a polyisocyanate (a) to OH group in a polyol (b) of more than 3.0, is used and the oligomer (A) has a mixing weight ratio of an oligomer (d) having a number average molecular weight of 800 or less to an oligomer (e) having a number average molecular weight of 1,000 or more of 30/70-70/30.The coating composition of this invention has a low viscosity, and therefore, is suitable for a rapid fiber-drawing in a production of an optical fiber. Further, a cured material obtained from the coating composition of the present invention has both a high elastic modulus and a high elongation, which properties are required for a hard material, and has a slight change of elastic modulus with a change of temperature to improve a long-term reliability of an optical fiber.Type: GrantFiled: April 24, 1998Date of Patent: May 2, 2000Assignees: Takeda Chemical Industries, Ltd., Shin-Etsu Chemical Co., Ltd.Inventors: Kyuya Yamazaki, Mitsuhiro Nishimura, Takashi Uemura, Akira Yamamoto, Shouhei Kozakai, Masatoshi Asano
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Patent number: 6031044Abstract: A polyurethane which is substantially self-dispersible in water and is obtainable by reactinga) at least one polyisocyanate withb) at least one polyol andc) at least one photoinitiator of the general formula I ##STR1## where R is a radical of the formula II ##STR2## or is --CR.sup.7 R.sup.8 R.sup.9, P(.dbd.O)(R.sup.10).sub.2 or SO.sub.2 R.sup.11,the number-average molecular weight M.sub.n of the polyurethane being greater than 2700, and its use. The invention also relates to aqueous polyurethane resin dispersions and coating compositions comprising the novel polyurethanes, and to their use.Type: GrantFiled: December 18, 1997Date of Patent: February 29, 2000Assignee: BASF AktiengesellschaftInventors: Nicolas Kokel, Harald Larbig, Klaus Menzel, Erich Beck, Wolfgang Reich, Guido Voit
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Patent number: 6023547Abstract: A radiation curable composition comprising a urethane oligomer with a polyester backbone which composition, when cured, has improved hydrolytic stability. The composition comprises a urethane oligomer, having a polyester backbone with a number average molecular weight of less than about 1000, wherein the polyester backbone is at least in part based on a diol component wherein at least one carbon at the .beta.-position with respect to a hydroxyl group bears two carbon-containing substituents having a total of at least three carbon atoms. Alternatively, when the composition comprises a urethane oligomer with a number average molecular weight of less than about 2000, having a polyester polyol backbone with a number average molecular weight of less than about 1000, the polyester backbone is at least in part based on a diol component wherein at least one carbon at the .beta.-position with respect to a hydroxyl group bears at least one carbon-containing substituent.Type: GrantFiled: June 9, 1997Date of Patent: February 8, 2000Assignee: DSM N.V.Inventor: Anthony J. Tortorello
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Patent number: 6017603Abstract: An ultraviolet-curable adhesive composition which comprises (A) a bisphenol type epoxy (meth)acrylate having a molecular weight of 450 to 3,000, (B) a urethane (meth)acrylate having a molecular weight of 400 to 10,000, (E) a (meth)acrylate monomer other than (A) and (B), and (F) a photopolymerization initiator, and an article having a cured layer of the above adhesive composition.Type: GrantFiled: December 22, 1997Date of Patent: January 25, 2000Assignee: Nippon Kayaku Kabushiki KaishaInventors: Kiyohisa Tokuda, Kenji Yoshida, Kazuhiko Ishii, Minoru Yokoshima
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Patent number: 6017973Abstract: A photocurable resin composition comprising (A) at least one urethane di- or triacrylate, which is a novel compound, (B) a radical polymeriable compound, and (C) a photopolymerization initiator, the weight ratio of the urethane acrylate (A) to the radical polymerizable compound (B) being 65/35 to 25/75; a method of producing a photo-cured object by photo-curing the above composition; a vacuum casting mold obtained by the above method; and a vacuum casting method using the above mold.Type: GrantFiled: May 16, 1997Date of Patent: January 25, 2000Assignee: Teijin Seiki Company, Ltd.Inventors: Yorikazu Tamura, Tsuneo Hagiwara, Yasushi Ishihama, Minoru Kayanoki, Takakuni Ueno
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Patent number: 5993960Abstract: A printing sheet having a high gloss and an enhanced ink-setting property has an outermost surface coating layer formed on a substrate sheet from an electron beam-cured resin produced from at least one electron beam-curable unsaturated organic compound having a dimer acid structure derived from unsaturated higher fatty acid.Type: GrantFiled: October 31, 1997Date of Patent: November 30, 1999Assignee: New Oji Paper Co., Ltd.Inventors: Yasufumi Nakayama, Masahiro Kamiya, Shinichi Nagasaki, Yoshihide Kawano, Toshifumi Fujii
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Patent number: 5990190Abstract: A photosensitive resin composition for cast molding, which has an ultraviolet transmittance of 0.05-5% as measured at a 1-mm thickness.Type: GrantFiled: July 15, 1997Date of Patent: November 23, 1999Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Shohei Nakamura, Kousi Anai
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Patent number: 5990192Abstract: Radiation-curable water-dilutable urethane resins obtainable by reacting cycloaliphatic and/or aromatic diisocyanates with a mixture of a (meth)acryloyl-containing dihydroxy compound in an amount such that the amount of reactive hydroxyl groups present therein is from 0.2 to 0.6 mol, and with a tri or tetrahydric polyol which has been partly esterified with (meth)acrylic acid and has a residual average hydroxyl functionality of from 1.0 to 1.4 in the molecule, in an amount such that the amount of the reactive hydroxyl groups is from 0.4 to 0.8 mol, the sum of the amounts of the reactive hydroxyl groups always being 1.0 mol, and from 40 to 60% of the isocyanate groups being converted into urethane groups, and reacting the resulting intermediate with an aliphatic saturated monocarboxylic acid having at least two hydroxyl groups in an amount such that the amount of the reactive hydroxyl groups is from 0.Type: GrantFiled: April 9, 1998Date of Patent: November 23, 1999Assignee: Vianova Resins AGInventors: Martin Gerlitz, Rami-Raimund Awad, Ulrike Kuttler, Thomas Fraydl, Martin Leitner, Andreas Kocsar
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Patent number: 5977200Abstract: An ultraviolet curable clearcoat composition comprising (exclusive of any solvent present): (a) about 30% to about 90% by weight of an acrylated aliphatic urethane having a molecular weight of about 1200 to 2600 and formed by the reaction of a multifunctional acrylate with a molecular weight of between about 110 and about 500 with an aliphatic urethane based on a polyether and having a molecular weight of about 800 to about 2200; (b) about 15% to about 70% by weight of a multifunctional acrylate having a molecular weight of about 170 to about 1000 and containing at least two polymerizable unsaturated groups per molecule; and (c) a photopolymerization initiator and/or sensitizer. Also described are preferred processes and clearcoated articles involving preferred clearcoat compositions.Type: GrantFiled: June 7, 1995Date of Patent: November 2, 1999Assignee: Red Spot Paint & Varnish Co., Inc.Inventor: Randall T. Lake
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Patent number: 5962547Abstract: Radiation- or thermally-initiated cationically-curable styrene oxides of the structure ##STR1## are suitable for use in cationically curable adhesive and coating compositions.Type: GrantFiled: May 14, 1998Date of Patent: October 5, 1999Inventors: Nikola A. Nikolic, Rose Ann Schultz