Sulfur Containing Patents (Class 522/180)
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Patent number: 5518789Abstract: A photopolymerizable composition comprising a crosslinking agent, a UV sensitive photopolymerization initiator and a thioether compound having a vinyl ester or vinyl amide component; wherein the crosslinking agent and the thioether may be the same compound.Type: GrantFiled: May 17, 1994Date of Patent: May 21, 1996Assignee: Eastman Kodak CompanyInventors: Elizabeth G. Burns, Susan A. Visser, Jeffrey F. Taylor
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Patent number: 5516455Abstract: A polymer dispersed liquid crystal composite prepared from: (1) at least one multifunctional electron-rich alkene that does not undergo appreciable homopolymerization and is selected from the group consisting of (a) vinyl ethers and vinyl sulfides; (b) keteneacetals, ketenethioacetals and methylene oxathiolanes, wherein the carbon of the carbon-carbon double bond not bearing the electron donating group has bonded to it H or a combination of H and a C1 to C.sub.6 alkyl, preferably a methyl group; (c) ortho or para vinyl phenyl ethers or thioethers (also known as styryloxy or styrylthio ether monomers); or (d) bicylic alkenes which have, as a result of their stereoelectronic configuration, unequal .pi.-electron density above and below the plane of the carbon-carbon double bond axis; (2) a multifunctional thiol; (3) a photoinitiator; and (4) liquid crystal material.Type: GrantFiled: February 17, 1995Date of Patent: May 14, 1996Assignee: Loctite CorporationInventors: Anthony F. Jacobine, John G. Woods, Margaret A. Rakas
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Patent number: 5459173Abstract: Stable thiol-ene compositions are provided which comprise a polythiol, a polyene and a stabilizer system comprising an alkenyl substituted phenolic compound having a formula: ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are independently selected from the group consisting of H, OR, a C.sub.1 -C.sub.8 alkyl, substituted alkyl, alkenyl or substituted alkenyl, a C.sub.6 -C.sub.20 aryl or substituted aryl, or a cyano group; R.sup.4 is H, R, OR, halogen, COR, COOR, or SR; R.sup.5 is OH, OR, OCOR, OCOOR, OCONHR, or OTMS; R is a C.sub.1 -C.sub.6 alkyl, a cycloalkyl, or a C.sub.6 -C.sub.20 caryl or substituted aryl; x and y are 1, 2, or 3; z is 0, 1, or 2; and x+y+z=2, 3, or 4; or a formula: ##STR2## where x, y, z, w, R.sup.1 R.sup.2 R.sup.3, R.sup.4 and R.sup.5 are defined as above, except that x+y+z=2-6, and R.sup.6 is CH.sub.2, C(CH.sub.3).sub.2, O, S, or SO.sub.Type: GrantFiled: June 22, 1993Date of Patent: October 17, 1995Assignee: Loctite CorporationInventors: David M. Glaser, Anthony F. Jacobine, Paul J. Grabek
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Patent number: 5459175Abstract: A curable thiol-ene composition specially adapted for use as a primary coating on optical fibers comprises a polythiol and a compound having a plurality of norbornene groups thereon, are characterized in that one of either the compound having the plurality of norbornene groups or the polythiol has a backbone of a poly(tetramethylene oxide), or is an oligomer thereof, and the poly(tetramethylene oxide) has a molecular weight of between 250 and 5,000. The formulations are relatively low viscosity liquids at practical application temperatures and cure substantially completely with very low irradiation fluence. The formulations cure in ambient air. There is no need to exclude oxygen or to control humidity. The formulations of the invention can be cured using low intensity UV lamps which do not generate significant amounts of heat. The cured products have excellent low temperature flexibility, good humidity and water absorbtion resistance and good thermal oxidative stability.Type: GrantFiled: June 22, 1993Date of Patent: October 17, 1995Assignee: Loctite CorporationInventors: John G. Woods, Margaret A. Rakas, Anthony F. Jacobine, Louis M. Alberino, Philip L. Kropp, Donna M. Sutkaitis, David M. Glaser, Steven T. Nakos
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Low yellow index polymer compositions, polymerisable compositions and lenses using said compositions
Patent number: 5442022Abstract: A polymer composition obtained by polymerisation of a polymerisable composition comprising: at least 50% by weight of a monomer or mixture of monomers having formula I ##STR1## wherein R.sub.1 and R.sub.2, which may be identical or different, represent hydrogen or C.sub.1 -C.sub.6 alkyl, X represents ##STR2## and wherein m+n is between 0 and 10, 0 to 50% by weight of one or more mono- or polyfunctional vinyl, acrylic or methacrylic comonomers (II); 0.5 to 15% by weight with respect to the weight of components (I) and (II) of a compound having formula (III) ##STR3## where R.sub.3 and R.sub.4 represent hydrogen or one of radicals R.sub.3 and R.sub.4 represents a hydrogen atom while the other forms a ring with R.sub.7 ; R.sub.5, R.sub.6 and R.sub.7 are hydrogen or an alkyl group which may be substituted by OH and/or interrupted.Type: GrantFiled: December 21, 1993Date of Patent: August 15, 1995Assignee: Essilor International-Compagnie General D'OptiqueInventors: Gabriel Keita, Joel Renaudineau -
Patent number: 5387445Abstract: A liquid crystal display device including two electrically insulating substrates, electrodes on the inner surfaces of the substrates, a film of liquid crystal material contained between the electrodes and a resinous material as sealant and/or encapsulant and/or inner structural component characterised in that the resinous material is the product of light-curing a light-curable resin composition comprising at least one compound having two or more non-aromatic carbon-carbon unsaturated bonds per molecule, at least one compound having two or more mercapto groups per molecule and a photoinitiator.Type: GrantFiled: March 9, 1992Date of Patent: February 7, 1995Assignee: Zeneca LimitedInventors: Shin Horiuchi, Sumio Wakabayashi, Takahisa Doba
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Patent number: 5371181Abstract: A treatment method for polythiol compounds used in thiol-ene formulations, especially formulations employing norbornene resins, significantly improves cure speed retention on aging of thiol-ene formulations which include hydroxylamine salts, such as N-nitrosoarylhydroxylamine aluminum salts, as shelf-life stabilizers. The treatment comprises contacting the polythiol with an amphoteric treating agent selected from the group consisting of silicated magnesium oxide, magnesium oxide, magnesium hydroxide, calcium oxide, calcium hydroxide, barium oxide, and barium hydroxide, and then separating the resin from the treating agent prior to mixture with a polyene to form a thiol-ene composition. In formulations employing phenolic compounds having an alkenyl group in conjugation with the phenyl group thereof as shelf-life co-stabilizers the treatment method also significantly enhances the shelf-life stability of the formulation compared to formulations made from untreated polythiol.Type: GrantFiled: June 22, 1993Date of Patent: December 6, 1994Assignee: Loctite CorporationInventors: David M. Glaser, Anthony F. Jacobine, Paul J. Grabek
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Patent number: 5360873Abstract: An actinic radiation-reactive pressure-sensitive adhesive composition which can be cured in air at a high speed, without irritation and bad smell, comprises1 a pressure-sensitive adhesive compound comprising an acrylate copolymer and2 an actinic radiation-curable resin comprising (1) one or more polythiol compounds and (2) one or more polyene compounds each having an least two actinic radiation-reactive acrylate carbon-to-carbon double bonds in the molecule.Type: GrantFiled: August 20, 1993Date of Patent: November 1, 1994Assignee: Asahi Denka Kogyo K.K.Inventors: Kazuo Ohkawa, Seiichi Saito
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Patent number: 5358976Abstract: Curable norbornene-thiol compositions are stabilized by addition of a non-acidic Nitroso compound.Type: GrantFiled: December 23, 1992Date of Patent: October 25, 1994Assignee: Loctite (Ireland) LimitedInventors: Joseph P. Dowling, Sarah C. Richardson, Killian Quigley
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Patent number: 5278199Abstract: An actinic radiation-reactive pressure-sensitive adhesive composition can be cured in air at a high speed, without irritation and bad smell, and comprises1 a pressure-sensitive adhesive organic compound, and2 an actinic radiation-curable resin comprising (1) one or more polythiol compounds and (2) one or more polyene compounds each having at least two actinic radiation-reactive carbon-to-carbon double bonds in the molecule.Type: GrantFiled: December 21, 1990Date of Patent: January 11, 1994Assignee: Asahi Denka Kogyo K.K.Inventors: Kazuo Ohkawa, Seiichi Saito
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Patent number: 5236967Abstract: An optical molding composition is used for casting and does not cause irritation to the skin or possess a bad smell. This composition comprises1. an actinic radiation-curable, radical-polymerizable organic compound comprising(1) one or more polythiol compounds and(2) one or more polyene compounds each having at least two actinic radiation-reactive carbon-to-carbon double bonds in the molecule, and2. an actinic radiation-sensitive radical polymerization initiator.Type: GrantFiled: February 18, 1992Date of Patent: August 17, 1993Assignee: Asahi Denka Kogyo K.K.Inventors: Kazuo Ohkawa, Seiichi Saito
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Patent number: 5190992Abstract: A photocurable resin composition for glass lamination, consisting essentially of a radical polymerizable monomer having at least one repeating units of ethylene oxide in its molecule and terminated with allyl, acrylate or methacrylate groups, and a photopolymerization initiator, a cured product of which has a volume resistivity of less than 5.times.10.sup.9 .OMEGA..multidot.cm. Addition of a polythiol provides an ene/thiol cure.Type: GrantFiled: October 1, 1991Date of Patent: March 2, 1993Assignee: Denki Kagaku Kogyo Kabushiki KaishaInventors: Toshiyuki Kato, Syunzi Ito, Tsunehiko Shimizui
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Patent number: 5167882Abstract: An improved stereolithography method for building a three-dimensional article including the steps of patternwise curing successive layers of a bath of curable liquid resin formulation until the article has been completely built up, removing the article from the liquid resin bath and then post-curing the article, wherein the liquid resin is a "thiol/nene" formulation including:(a) a first compound having a plurality of norbornene groups thereon;(b) a second compound having a plurality of thiol groups therein; and(c) a free radical photoinitiator,the total functionality of the formulation being greater than 4.Type: GrantFiled: February 5, 1991Date of Patent: December 1, 1992Assignee: Loctite CorporationInventors: Anthony F. Jacobine, Margaret A. Rakas, David M. Glaser
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Patent number: 5130392Abstract: Radiation-sensitive polymers suitable for use in positive- and negative-working recording elements contain not only acid-labile groups but also onium salt groups having nonnucleophilic counterions in one and the same molecule.Type: GrantFiled: January 9, 1990Date of Patent: July 14, 1992Assignee: BASF AktiengesellschaftInventors: Reinhold Schwalm, Andreas Boettcher
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Patent number: 5100929Abstract: Photopolymerizable dental compositions are proposed which are curable with visible light and which apart from usual auxiliary substances and additives contain polymerizable monomers of the group of the poly-thiol compounds and of the group of the poly-ene compounds and a photoinitiator and which, in order to obtain a curing free from any smeary layer, contain at least 10% by weight poly-thiol compound(s), at least 10% by weight poly-ene compound(s) and 0.01 to 5% by weight of at least one acyl phosphine compound as photoinitiator. The compositions can advantageously be used as dental impression compositions.Type: GrantFiled: October 30, 1989Date of Patent: March 31, 1992Assignee: Espe Stiftung & Co. Produktion- und Vertriebs KGInventors: Peter Jochum, Oswald Gasser, Erich Wanek, Rainer Guggenberger, Klaus Ellrich
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Patent number: 5089601Abstract: A chloroprene polymer having dithiocarbamate groups at both terminals, represented by the following formula (I): ##STR1## wherein M.sub.1 is a chloroprene monomer residue; X is a group represented by the following formula (II): ##STR2## wherein R.sub.1 is a C.sub.1 -C.sub.8 alkyl group, R.sub.2 is a C.sub.1 -C.sub.8 alkyl group or a hydrogen atom, R.sub.1 and R.sub.2 may be the same or different, or R.sub.1 and R.sub.2 together form a C.sub.3 -C.sub.8 methylene group so that they form a cyclic group together with the adjacent nitrogen atom, or a group represented by the following formula (III): ##STR3## wherein R.sub.1 is a C.sub.1 -C.sub.8 alkyl group, and R.sub.2 is a C.sub.1 -C.sub.8 alkyl group or a hydrogen atom; and n is a natural number of from 10 to 5,000 when X is the group of the formula (II) or a natural number of form 5 to 100 when X is the group of the formula (III).Type: GrantFiled: September 7, 1990Date of Patent: February 18, 1992Assignee: Tosoh CorporationInventors: Shinji Ozoe, Hiroshi Yamakawa
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Patent number: 4929403Abstract: A process for rapidly forming a flexible mold for finely detailed objects from a radiatively curable molding composition includes coating at least a portion of the surface of a three-dimensional object with a fluid molding composition. The coating is cured by exposing the fluid coating to radiative energy to form an elastic, flexible layer of cured molding composition on the object. The coating and curing steps can be repeated to build up the flexible mold until a predetermined minimum has been attained. The cured molding composition is removed from the object, and is suitable for immediate use as a mold to cast duplicate reproductions of the object.Type: GrantFiled: July 25, 1989Date of Patent: May 29, 1990Inventor: Edwin F. Audsley
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Patent number: 4808638Abstract: A curable thiol-ene formulation comprising(a) a polythiol(b) a 'ene compound having a plurality of groups of the formula: ##STR1## where Q is CH.sub.2, CHCH.sub.3, C(Ch.sub.3).sub.2, O, S, NR.sup.1 or SO.sub.2 R.sup.1 is H or alkyl, and m is 0-10, and(c) an effective amount of a free radical initiator.Type: GrantFiled: September 21, 1987Date of Patent: February 28, 1989Assignee: Loctite CorporationInventors: Walter J. Steinkraus, John Woods, John M. Rooney, Anthony F. Jacobine, David M. Glaser
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Patent number: 4604411Abstract: An improved process for preparing a sticky water-soluble polymer, e.g. acrylamide polymers and acrylic acid polymers, which comprises polymerizing an aqueous solution of a monomer in a polymerization vessel of which the surface contacting the aqueous monomer solution is covered with a tetrafluoroethylene-ethylene copolymer film, whereby the stickiness of the produced polymer to the vessel is remarkably decreased, namely the peelability of the polymer from the vessel is remarkably improved, and moreover the polymerization conversion is remarkably improved. Also, the use of a metal deposited tetrafluoroethylene-ethylene copolymer film as a covering material improves the efficiency of a photopolymerization and enables to use a polymerization vessel made of an inexpensive material.Type: GrantFiled: January 4, 1985Date of Patent: August 5, 1986Assignee: Dai-Ichi Kogyo Seiyaku Co., Ltd.Inventors: Akira Yada, Shusaku Matsumoto, Yoshihiro Kawamori, Takao Saito, Tadashi Nishiyama, Yoshitugu Adachi