Sulfur Containing Patents (Class 522/180)
  • Patent number: 5518789
    Abstract: 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: Grant
    Filed: May 17, 1994
    Date of Patent: May 21, 1996
    Assignee: Eastman Kodak Company
    Inventors: Elizabeth G. Burns, Susan A. Visser, Jeffrey F. Taylor
  • Patent number: 5516455
    Abstract: 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: Grant
    Filed: February 17, 1995
    Date of Patent: May 14, 1996
    Assignee: Loctite Corporation
    Inventors: Anthony F. Jacobine, John G. Woods, Margaret A. Rakas
  • Patent number: 5459173
    Abstract: 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: Grant
    Filed: June 22, 1993
    Date of Patent: October 17, 1995
    Assignee: Loctite Corporation
    Inventors: David M. Glaser, Anthony F. Jacobine, Paul J. Grabek
  • Patent number: 5459175
    Abstract: 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: Grant
    Filed: June 22, 1993
    Date of Patent: October 17, 1995
    Assignee: Loctite Corporation
    Inventors: John G. Woods, Margaret A. Rakas, Anthony F. Jacobine, Louis M. Alberino, Philip L. Kropp, Donna M. Sutkaitis, David M. Glaser, Steven T. Nakos
  • Patent number: 5442022
    Abstract: 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: Grant
    Filed: December 21, 1993
    Date of Patent: August 15, 1995
    Assignee: Essilor International-Compagnie General D'Optique
    Inventors: Gabriel Keita, Joel Renaudineau
  • Patent number: 5387445
    Abstract: 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: Grant
    Filed: March 9, 1992
    Date of Patent: February 7, 1995
    Assignee: Zeneca Limited
    Inventors: Shin Horiuchi, Sumio Wakabayashi, Takahisa Doba
  • Patent number: 5371181
    Abstract: 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: Grant
    Filed: June 22, 1993
    Date of Patent: December 6, 1994
    Assignee: Loctite Corporation
    Inventors: David M. Glaser, Anthony F. Jacobine, Paul J. Grabek
  • Patent number: 5360873
    Abstract: 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: Grant
    Filed: August 20, 1993
    Date of Patent: November 1, 1994
    Assignee: Asahi Denka Kogyo K.K.
    Inventors: Kazuo Ohkawa, Seiichi Saito
  • Patent number: 5358976
    Abstract: Curable norbornene-thiol compositions are stabilized by addition of a non-acidic Nitroso compound.
    Type: Grant
    Filed: December 23, 1992
    Date of Patent: October 25, 1994
    Assignee: Loctite (Ireland) Limited
    Inventors: Joseph P. Dowling, Sarah C. Richardson, Killian Quigley
  • Patent number: 5278199
    Abstract: 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: Grant
    Filed: December 21, 1990
    Date of Patent: January 11, 1994
    Assignee: Asahi Denka Kogyo K.K.
    Inventors: Kazuo Ohkawa, Seiichi Saito
  • Patent number: 5236967
    Abstract: 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: Grant
    Filed: February 18, 1992
    Date of Patent: August 17, 1993
    Assignee: Asahi Denka Kogyo K.K.
    Inventors: Kazuo Ohkawa, Seiichi Saito
  • Patent number: 5190992
    Abstract: 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: Grant
    Filed: October 1, 1991
    Date of Patent: March 2, 1993
    Assignee: Denki Kagaku Kogyo Kabushiki Kaisha
    Inventors: Toshiyuki Kato, Syunzi Ito, Tsunehiko Shimizui
  • Patent number: 5167882
    Abstract: 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: Grant
    Filed: February 5, 1991
    Date of Patent: December 1, 1992
    Assignee: Loctite Corporation
    Inventors: Anthony F. Jacobine, Margaret A. Rakas, David M. Glaser
  • Patent number: 5130392
    Abstract: 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: Grant
    Filed: January 9, 1990
    Date of Patent: July 14, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Reinhold Schwalm, Andreas Boettcher
  • Patent number: 5100929
    Abstract: 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: Grant
    Filed: October 30, 1989
    Date of Patent: March 31, 1992
    Assignee: Espe Stiftung & Co. Produktion- und Vertriebs KG
    Inventors: Peter Jochum, Oswald Gasser, Erich Wanek, Rainer Guggenberger, Klaus Ellrich
  • Patent number: 5089601
    Abstract: 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: Grant
    Filed: September 7, 1990
    Date of Patent: February 18, 1992
    Assignee: Tosoh Corporation
    Inventors: Shinji Ozoe, Hiroshi Yamakawa
  • Patent number: 4929403
    Abstract: 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: Grant
    Filed: July 25, 1989
    Date of Patent: May 29, 1990
    Inventor: Edwin F. Audsley
  • Patent number: 4808638
    Abstract: 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: Grant
    Filed: September 21, 1987
    Date of Patent: February 28, 1989
    Assignee: Loctite Corporation
    Inventors: Walter J. Steinkraus, John Woods, John M. Rooney, Anthony F. Jacobine, David M. Glaser
  • Patent number: 4604411
    Abstract: 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: Grant
    Filed: January 4, 1985
    Date of Patent: August 5, 1986
    Assignee: Dai-Ichi Kogyo Seiyaku Co., Ltd.
    Inventors: Akira Yada, Shusaku Matsumoto, Yoshihiro Kawamori, Takao Saito, Tadashi Nishiyama, Yoshitugu Adachi