With Ethylenically Unsaturated Reactant Patents (Class 528/376)
  • Patent number: 5998564
    Abstract: 2.2'-bis(3-mercaptophenyl)hexafluoropropane [bisthio-phenol AF] is obtained in good yield by chlorosulfonating 2.2'-bisphenylhexafluoropropane and reducing the thus quantitatively obtained 2,2'-bis(3-chlorosulfonylphenyl)-hexafluoropropane with zinc under acidic conditions and is effectively used as a cross-linking agent for a fluorine-containing elastomer having halogenophenyl groups as cross-linkable groups.
    Type: Grant
    Filed: January 22, 1999
    Date of Patent: December 7, 1999
    Assignee: Nippon Mektron, Limited
    Inventors: Takehiro Sonoi, Haruyoshi Tatsu, Satoru Saito, Sergei Rafailovich Sterlin, Victor Filippovich Cherstokov, Nina Ivanovna Delyagina
  • Patent number: 5994496
    Abstract: A conjugated polymer in an oxidized state has a doping level of 0.4 or higher. In said oxidized state the polymer is electroconductive, transparent to visible light and preferably colorless. A method of preparing such a polymer comprises the step of bringing the polymer into contact with a strong oxidative agent such as thianthrenium perchlorate. Layers of such polymers may be used as a transparent coating on a display device or as an electrode layer in an electroluminescent device.
    Type: Grant
    Filed: November 5, 1998
    Date of Patent: November 30, 1999
    Assignee: U.S. Philips Corporation
    Inventors: Johannes A. E. H. Van Haare, Rene A. J. Janssen, Dagobert M. De Leeuw
  • Patent number: 5976422
    Abstract: Describes a polymerizable organic composition comprising at least one polymerizable monomer having at least two ethylenically unsaturated groups, e.g., divinyl benzene, and a polythiol monomer represented by the following general formula, ##STR1## wherein R.sub.1 and R.sub.2 are each selected from the group consisting of straight or branched chain alkylene, e.g., methylene or ethylene, cyclic alkylene, phenylene and C.sub.1 -C.sub.9 alkyl substituted phenylene. Optionally, a monoethylenically unsaturated monomer, e.g., phenoxyethyl methacrylate, and/or an anhydride monomer, e.g., methacrylic anhydride, may also be present. Polymerizates prepared from polymerizable organic compositions of the present invention have a refractive index of at least 1.57, an Abbe number of at least 33 and an initial Barcol hardness of at least 1. Also described are photochromic articles prepared from such compositions.
    Type: Grant
    Filed: March 9, 1998
    Date of Patent: November 2, 1999
    Assignee: PPG Industries Ohio, Inc.
    Inventors: Michael O. Okoroafor, Robert D. Herold, Robert A. Smith
  • Patent number: 5959071
    Abstract: A polythioether has the formulaR.sup.1 --?--R.sup.2 --S--CH(CH.sub.3)--S--!.sub.n --R.sup.2 --R.sup.1whereinR.sup.1 denotes a thiol group, a hydroxyl group, an unsubstituted amine group, a monoalkyl-substituted amine group, a monovalent radical substituted with at least one hydroxyl group, unsubstituted amine group or monoalkyl-substituted amine group, or a group that is non-reactive in the presence of an acid catalyst,R.sup.2 denotes a divalent radical, andn is an integer from 1 to 60.The polythioether is a liquid at room temperature and pressure.
    Type: Grant
    Filed: March 31, 1998
    Date of Patent: September 28, 1999
    Assignee: Courtaulds Aerospace, Inc.
    Inventors: Suzanna Elaine DeMoss, Jonathan Doherty Zook
  • Patent number: 5955206
    Abstract: A composition for polysulfide-based resin comprising a polythiol having 4 or more functional groups and a compound having a reactive unsaturated bond(s) and/or b epoxy group(s) and/or c iso(thio)cyanato group(s) in one molecule (however, a+b+c.gtoreq.2, and a and b are not simultaneously 0). A polysulfide-based resin obtained by curing the composition, an optical material comprising the resin, a lens consisting of the optical material and a method for producing the polysulfide-based resin are also set forth.
    Type: Grant
    Filed: April 30, 1996
    Date of Patent: September 21, 1999
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Koju Okazaki, Chitoshi Shimakawa, Mamoru Tanaka, Yoshinobu Kanemura, Teruyuki Nagata, Yoshihiro Irizato, Shinichi Umeda
  • Patent number: 5945464
    Abstract: The ultraviolet-curable, resin-forming composition which comprises a polycarbonic acid ester such as diethylene glycol bis(allyl carbonate), a polythiol such as pentaerythritol tetrakis(3-mercaptopropionate) and an ultraviolet curing agent. The resin-forming composition can be photopolymerized in an atmospheric condition, and the thus produced resin has an elongated durability as well as excellent properties with regard to a transparency, heat resistance, adhesion property, resistance to shock, dyeing property and others.
    Type: Grant
    Filed: August 13, 1997
    Date of Patent: August 31, 1999
    Assignee: Asahi Kogaku Kogyo Kabushiki Kaisha
    Inventors: Hidenori Takushima, Kouji Futaki
  • Patent number: 5942555
    Abstract: A photoactivatable reagent useful as a chain transfer reagent for providing a semitelechelic polymer having one or more terminal photoactivatable groups. The reagent provides one or more photoactivatable groups and one or more sulfhydryl (or other chain transfer) groups, the photoactivatable and chain transfer groups optionally being joined together by a spacer group. The reagent can be used to prepare a polymer by serving to initiate the polymerization of ethylenically unsaturated monomers. The reagent itself becomes an integral part of the resultant polymer, thereby providing the polymer with a terminal photoactivatable nature. The method provides a number of benefits, including the ability to provide homogeneous photoactivatable polymer compositions, e.g., in terms of the uniform location of the photogroup(s) on the terminal portion of each polymer molecule and the ability to build a desired nonpolar quality, and in turn improved surfactancy, into otherwise polar polymers.
    Type: Grant
    Filed: March 21, 1996
    Date of Patent: August 24, 1999
    Assignee: SurModics, Inc.
    Inventors: Melvin J. Swanson, Richard A. Amos, Dale G. Swan, Gary W. Opperman
  • Patent number: 5916956
    Abstract: In a multi-stage process for producing a substantially unvulcanized elastomer composition, a masterbatch is produced by thermomechanical working in a first or other early stage of the multi-stage process. The masterbatch comprises sulfur crosslinkable hydrocarbon elastomer in which is substantially dispersed, particulate fillers, for example carbon black or silicon-treated carbon black, modified carbon black and/or silica and sulfur crosslinking agent effective to crosslink the hydrocarbon elastomer and selected from sulfur donors and sulfur. The filler and sulfur crosslinking agent can be mixed together as a pre-blend prior to being added to the elastomer. The substantially unvulcanized elastomer is then produced in one or more later stages of the multi-stage process, involving further theromechanical working of the masterbatch. A curative additive comprising accelerator, and optionally additional sulfur crosslinking agent, is added and dispersed in the elastomer in the last stage of the multistage process.
    Type: Grant
    Filed: January 16, 1997
    Date of Patent: June 29, 1999
    Assignee: Cabot Corporation
    Inventors: Meng-Jiao Wang, Trevor Alan Brown, Ralph E. Dickinson
  • Patent number: 5869598
    Abstract: An inexpensive block polymer which is effectively available in various uses with regard to hot-melt resin compositions, pressure sensitive adhesives, carriers for pressure sensitive adhesives, and the like. This block polymer has a structure including a polyvalent mercaptan segment at its center from which two or more polymer segments are radially extended. The number-average molecular weight of this polymer is in a range of 2,000 to 1,000,000, and the two or more polymer segments have two or more different compositions. This block polymer is obtainable by a process including two or more steps of radical polymerization of polymerizable monomer components having different compositions using a polyvalent mercaptan as a polymerization initiator.
    Type: Grant
    Filed: June 10, 1997
    Date of Patent: February 9, 1999
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Masatoshi Yoshida, Nobuhiro Kobayashi, Hiroaki Hasegawa
  • Patent number: 5840823
    Abstract: Aqueous polyurethane dispersions having latent crosslinking properties containI) a disperse phase (P.I), containingIa) a polyurethane (PUR.Ia) which, in addition to groups which impart water dispersibility to the polyurethane, carries groups which have a C--C double bond and in which the double bond is activated by a carbonyl group bonded directly therewith, orIb) a mixture ofa polyurethane (PUR.Ib) which carries groups which impart water dispersibility to the polyurethane but not groups which have a C--C double bond and in which the double bond is activated by a carbonyl group bonded directly therewith anda compound (V.I) which differs from the polyurethanes PUR.Ia and PUR.Ib, and which carries groups which have a C--C double bond and in which the double bond is activated by a carbonyl group bonded directly therewith andII) a disperse phase (P.II) containing a compound which differs from the compounds (PUR.Ia), (PUR.Ib) and (V.
    Type: Grant
    Filed: February 25, 1997
    Date of Patent: November 24, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Ulrike Licht, Nicolas Kokel, Karl Haberle, Renate Wustefeld
  • Patent number: 5760142
    Abstract: Epoxide-amine dendrimers synthesized by a repetitive and step-wise addition reaction of epoxides comprising functional moieties which are available for conversion into amino groups followed by a reaction of these groups to primary amino moieties. The amino terminated dendrimers are reacted with (2,3-epoxypropoxy) methacrylate, a monoepoxide and/or a monoisocyante. The methacrylate terminated dendrimers are polymerizable using redox initiators and/or photoinitiators. The resulting dendrimers show a very low volume shrinkage from that of the starting materials, on the order of less than about 5 percent by volume.
    Type: Grant
    Filed: December 4, 1996
    Date of Patent: June 2, 1998
    Assignee: Dentsply DeTrey G.m.b.H.
    Inventor: Joachim E. Klee
  • Patent number: 5741884
    Abstract: Processes for making poly(thioether ether)s and hydroxy-terminated poly(thioether ether)s are disclosed. The poly(thioether ether)s are made by bulk free-radical polymerization of diallyl ether and an aliphatic C.sub.2 -C.sub.10 dithiol. Liquid polymers are obtained when mixtures of two or more dithiols are used. Hydroxy-terminated products are obtained by reacting the poly(thioether ether)s with allyl alcohol under free-radical conditions.
    Type: Grant
    Filed: June 2, 1995
    Date of Patent: April 21, 1998
    Assignee: Arco Chemical Technology, L.P.
    Inventors: Gangfeng Cai, Robert G. Gastinger
  • Patent number: 5728749
    Abstract: This photopolymerizable composition includes an grafted reactive telomer containing trifluoroethyl methacrylate units, a reactive diluent and a photopolymerization initiator. It gives hydrophobic transparent coatings.
    Type: Grant
    Filed: November 30, 1995
    Date of Patent: March 17, 1998
    Assignee: Elf Atochem S.A.
    Inventors: Didier Vanhoye, Elsa Ballot, Robert Legros, Olivier Loubet, Bernard Boutevin, Bruno Ameduri
  • Patent number: 5679762
    Abstract: An inexpensive block polymer which is effectively available in various uses with regard to hot-melt resin compositions, pressure sensitive adhesives, carriers for pressure sensitive adhesives, and the like. This block polymer has a structure including a polyvalent mercaptan segment at its center from which two or more polymer segments are radially extended. The number-average molecular weight of this polymer is in a range of 2,000 to 1,000,000, and the two or more polymer segments have two or more different compositions. This block polymer is obtainable by a process including two or more steps of radical polymerization of polymerizable monomer components having different compositions using a polyvalent mercaptan as a polymerization initiator.
    Type: Grant
    Filed: August 18, 1995
    Date of Patent: October 21, 1997
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Masatoshi Yoshida, Nobuhiro Kobayashi, Hiroaki Hasegawa
  • Patent number: 5679763
    Abstract: A composition exhibiting a second order nonlinear optical properties containing a non-centrosymmetric aromatic nonlinear optical compound possessing a delocalized resonance configuration as a guest in a host polyquinoline polymer matrix.
    Type: Grant
    Filed: February 24, 1995
    Date of Patent: October 21, 1997
    Assignee: Enichem S.p.A.
    Inventors: Kwan-Yue Alex Jen, Yongming Cai
  • Patent number: 5659047
    Abstract: The invention relates to compounds of formula: ##STR1## in which: w is 0, 1 or 2;x is between 2 and 10;y is between 0 and 5;R denotes a methyl, ethyl, hydroxyethyl or benzyl radical;X.sup..crclbar. denotes an inorganic or organic anion; andn is an integer or decimal number between 1 and 15;the [C.sub.5 H.sub.6 N.sub.2 R.sup.+ ] group representing the following structures, taken as a mixture or individually: ##STR2## as well as their use as a biocidal agent or preservative.
    Type: Grant
    Filed: September 13, 1995
    Date of Patent: August 19, 1997
    Assignee: L'Oreal
    Inventors: Guy Vanlerberghe, Eric Bollens, Claude Mahieu, Henri Sebag
  • Patent number: 5643998
    Abstract: A recyclable polymer is formed of a plurality of oligomer units obtained by polymerizing a fixed number of monomers, and linkage units for linking the oligomer units through a chemical bond which is different from a bond between monomers constituting the oligomer units, thereby allowing repetitive scission and re-bonding of the linkage units by a predetermined treatment not cleaving the bond between monomers. The recyclable polymer is decomposable into oligomers and the oligomers can be linked again into the original polymer without degrading the quality of the polymer. A process for producing the recyclable polymer, a method for recovering the recyclable polymer, and a method for regenerating the recyclable polymer are also provided.
    Type: Grant
    Filed: March 8, 1995
    Date of Patent: July 1, 1997
    Assignee: Kabushiki Kaisha Toyota Chuo Kenkyusho
    Inventors: Mitsuru Nakano, Arimitsu Usuki, Akane Okada, Osami Kamigaito
  • Patent number: 5612402
    Abstract: The invention relates to a curable polysulfide composition, which has an application in making a preserving coating, and an insulator in the field of road construction, house building, etc. The target of the invention is to obtain a stable polysulfide curable composition for which the cure rate and the cure velocity are independent of the surrounds, to allow the obtaining of vulcanized material with high grade of technical and ecological parameters, avoiding the typical unpleasant smell of mercaptane polysulfides and the toxicity of the curing agents, additives and fillers. The problems is solved using the following curable polysulfide composition: polysulfide polymer and/or copolymer containing up to 1 mol/kg SH groups, with molecular weight from 2,000 to 200,000, polysulfide degree from 2.2 to 4.0, ramification rate up to 4 mol percent and degree of polymerization of 20 to 500 in an amount of 90 to 110 pbw; modifier up to 75 pbw; curing agent from 0.
    Type: Grant
    Filed: January 23, 1995
    Date of Patent: March 18, 1997
    Inventors: Liliana S. Orecharova, Emil S. Vassev, Rossislav L. Orecharov, Petko L. Orecharov
  • Patent number: 5594090
    Abstract: A first prepolymer contains a structural unit represented by the formula ##STR1## where m denotes a positive number of from 2 to 20 with a polymerization degree of 2 to 1000. A second prepolymer contains a structural unit represented by the formula ##STR2## where X denotes a hydrogen atom or a halogen atom, m.sup.1 and m.sup.2 denote positive numbers of from 2 to 20 and n.sup.1 +n.sup.2 denote positive numbers of from 2 to 1000, with n.sup.1 and n.sup.2 being not equal to 0, the prepolymer having a polymerization degree of 2 to 1000. An optical material with a high refractive index is obtained by polymerizing and curing a polymerizable composition containing the first or second prepolymer.
    Type: Grant
    Filed: April 4, 1995
    Date of Patent: January 14, 1997
    Assignee: NOF Corporation
    Inventors: Tsuyoshi Miyazaki, Hiromitsu Nakajima, Shuji Ichikawa, Yasumi Koinuma, Kazuo Matsuyama, Koji Kamenosono, Yoshihiro Minoshima
  • Patent number: 5558937
    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: May 3, 1995
    Date of Patent: September 24, 1996
    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: 5543482
    Abstract: The present invention provides a composition comprising a vinylbenzylthio compound represented by the following general formula ##STR1## in which m is an integer of 2-3, n is an integer of 1 and R is a hydrocarbon group of 3-6 carbon atoms or a hydrocarbon group of 3-6 carbon atoms containing a bivalent sulfur atom, and a monomer radical-copolymerizable with said vinylbenzylthio compound.Said composition is useful for producing a plastic lens having a high refractive index, a small specific gravity, excellent heat resistance and excellent processability.
    Type: Grant
    Filed: March 13, 1995
    Date of Patent: August 6, 1996
    Assignee: Mitsubishi Gas Chemical Co., Inc.
    Inventors: Masanori Shimuta, Toru Takahashi, Hisato Abe, Kenichi Takahashi, Akira Kurata, Osamu Aoki
  • 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: 5502139
    Abstract: A cross-linkable polymeric casting composition includinga fluorene diacrylate or dimethacrylate monomer; anda comonomer including a polymerisable double bond.
    Type: Grant
    Filed: April 20, 1995
    Date of Patent: March 26, 1996
    Assignee: Sola International Holdings Ltd.
    Inventors: Huan K. Toh, Chong M. Kok
  • Patent number: 5493000
    Abstract: This invention relates to a branched fractal three dimensional porous polymer species which comprises rigid aromatic recurring units having electrophilic or nucleophilic reactive moieties on the exterior thereof. Another aspect of this invention relates to a star polymer comprising a polymeric core formed of the fractal polymers (FPS) of this invention having linear polymeric moieties grafted to the exterior thereof by way of residues formed by reaction between the reactive moieties on the exterior of the fractal polymer (FP) and complimentary reactive moieties on a linear polymer. Yet another aspect of this invention relates to polymeric composites comprising a polymer matrix having dispersed therein the star polymers of this invention.
    Type: Grant
    Filed: August 23, 1993
    Date of Patent: February 20, 1996
    Assignee: AlliedSignal Inc.
    Inventor: Shaul M. Aharoni
  • Patent number: 5473048
    Abstract: The invention provides a co-polymer having a hub portion from which radiate from 3 to 8 arms where the hub portion is the residue of a tri-functional to octa-functional thiol and each arm is an addition polymer comprising structural units and functional units that are mutually compatible, the functional units including crosslinking substituents capable of undergoing a crosslinking reaction with a crosslinking agent or crosslinking substituent in functional units in another molecule of the same polymer and optionally compatible auxiliary functional units that contain wetting groups.
    Type: Grant
    Filed: February 28, 1991
    Date of Patent: December 5, 1995
    Assignee: Imperial Chemical Industries, PLC
    Inventor: Manish Sarkar
  • 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: 5422422
    Abstract: The invention relates to a high refractive index plastic produced by reaction of an alkylthiol with a multiply unsaturated monomer, wherein said alkylthiol (A) has at least 2, and up to 20 carbon atoms in the alkyl group, and contains at least 2 thiol groups in the molecule, is reacted with an alkylpolythiol ester (B) having at least 2, and up to 24, preferably up to 12, carbon atoms in the alkyl group, which ester contains at least 2 thiol groups esterified with (meth)acrylic acid in the molecule, said reaction being under conditions of radical polymerization, with the limitation that the numerical ratio of the mercapto groups to the available double bonds is .ltoreq.1, preferably <0.5.
    Type: Grant
    Filed: October 12, 1993
    Date of Patent: June 6, 1995
    Assignee: Roehm GmbH Chemische Fabrik Patentabteilung
    Inventors: Martina Bader, Volker Kerscher
  • 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: 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: 5352757
    Abstract: The present invention relates to new sulfur compounds which are polyol esters of mercaptocarboxylic acids. It also relates to the use of these sulfur esters for preparing polymers exhibiting a refractive index higher than 1.50. The manufacture of optical discs and of waveguides may be mentioned among the optical applications of these polymers.
    Type: Grant
    Filed: September 16, 1992
    Date of Patent: October 4, 1994
    Assignee: Rhone-Poulenc Chimie
    Inventors: Sylvie Lavault, Gerard Velleret
  • Patent number: 5288844
    Abstract: Disclosed herein is a high-refractive index plastic optical material comprising a copolymer obtained by subjecting a mixture composed of a component A consisting of a dithiol compound represented by the formula I: ##STR1## wherein n stands for an integer of 1-3, and a component B consisting of divinylbenzene, said mixture containing both components in such a manner that the proportion of the component A to the component B is 0.25-3.5 in terms of weight ratio, to addition polymerization and having a refractive index of at least 1.63 and an Abbe's number of at least 27. The optical material has excellent optical properties that the refractive index is high and the dispersion is low, and moreover possesses good physical properties.
    Type: Grant
    Filed: July 2, 1992
    Date of Patent: February 22, 1994
    Inventor: Teruo Sakagami
  • Patent number: 5260411
    Abstract: A method for the preparation of a polyimide containing reversible crosslinks comprising the step of curing a monomer having the formula ##STR1## wherein R and R' may be the same or different and each is H or lower alkyl having 1-5 carbon atoms under conditions conducive to the formation of a polyimide and thereby forming a polyimide having the formula ##STR2## R and R' are as defined above and n is an integer from 10 to 100. The polyimide may be converted to a soluble polymer by cleaving the disulfide bond in the presence of a solvent and a reducing agent. The reduced polymer may be reformed into the polymer in an oxidation step or into a modified polyimide in other reaction steps. Copolymerization processes are also disclosed.
    Type: Grant
    Filed: April 20, 1988
    Date of Patent: November 9, 1993
    Assignee: Polytechnic University
    Inventors: Giuliana C. Tesoro, Vinod R. Sastri
  • 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: 5227463
    Abstract: A process is provided for the production of functional group containing resins wherein an alkyl-dithiol is added to the polymerizing mixture of styrene and divinyl benzene part way through the polymerization. On completion of the polymerization, the product is a thiol functionalized styrene-divinyl benzene resin.
    Type: Grant
    Filed: June 12, 1992
    Date of Patent: July 13, 1993
    Assignee: Polysar Rubber Corporation
    Inventor: Gilles J. Arsenault
  • 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: 5191061
    Abstract: A cured resin for high-fraction lenses is disclosed, which is obtained by polymerizing a composition comprising (A) from 70 to 99 parts by weight of a sulfur-containing aromatic (meth)acrylate represented by formula (I): ##STR1## wherein R.sup.1 represents a hydrogen atom or a methyl group; R.sup.2 represents an alkylene group; Ar represents an arylene group, an arylene group substituted with a halogen atom except a fluorine atom, an aralkylene group, or an aralkylene group substituted with a halogen atom except a fluorine atom; X represents --O-- or --S--; Y represents --S-- or --SO.sub.2 -- when X is --O--, or Y represents --S--, --SO.sub.
    Type: Grant
    Filed: October 18, 1991
    Date of Patent: March 2, 1993
    Assignee: Misubishi Petrochemical Co., Ltd.
    Inventors: Yukihito Zanka, Seiichiro Hayakawa, Tsutomu Isaka, Fumie Watari
  • Patent number: 5182360
    Abstract: Tris(norbornenyl) isocyanurate compounds of the formula: ##STR1## wherein R.sup.1 is either H or methyl group, are prepared from the base-catalyzed trimerization of norbornenyl isocyanate. Tris(norbornenyl) isocyanurate is suitable for use as a crosslinker in thiol-ene formulations containing a difunctional thiol oligomer or in systems containing norbornene-difunctional oligomers and polyfunctional thiols, producing improved high temperature properties for the cured compositions.
    Type: Grant
    Filed: October 17, 1991
    Date of Patent: January 26, 1993
    Assignee: Loctite Corporation
    Inventors: Anthony F. Jacobine, Steven T. Nakos
  • 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: 5112937
    Abstract: Disclosed are polymers of average molecular weight ranging from 400 to 20,000 comprising thiosubstituted groups per molecule and resulting from the reaction, in the presence of an addition catalyst, of at least one compound with a thiol function, having 1 to 60 carbon atoms per molecule, with an unsaturated polyester resulting from the condensation of an aliphatic epoxide with an unsaturated aliphatic dicarboxylic compound comprising at least one ethylenic unsaturation in the alpha position of one of the carboxyl groups. Also disclosed are middle distillate compositions having a distillation range from 150.degree. to 450.degree. C. and comprising a minor proportion, preferably from 0.001 to 2% by weight, of at least one of the polymers defined hereinabove.
    Type: Grant
    Filed: May 10, 1991
    Date of Patent: May 12, 1992
    Assignees: Institut Francais du Petrole, Elf France
    Inventors: Jacques Garapon, Remi Touet, Bernard Damin, Beatrice Debled
  • Patent number: 5087758
    Abstract: The present invention relates to a mercapto compound, a process for preparing the mercapto compound, a process for preparing a polythiourethane base resin containing the mercapto compound, and a process for preparing plastic lenses containing the resin.
    Type: Grant
    Filed: August 29, 1989
    Date of Patent: February 11, 1992
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Yoshinobu Kanemura, Katsuyoshi Sasagawa, Masao Imai, Toshiyuki Suzuki
  • Patent number: 5037945
    Abstract: Disclosed are polymers of average molecular weight ranging from 400 to 20,000 comprising thiosubstituted groups per molecule and resulting from the reaction, in the presence of an addition catalyst, of at least one compound with a thiol function, having 1 to 60 carbon atoms per molecule, with an unsaturated polyester resulting from the condensation of an aliphatic epoxide with an unsaturated aliphatic dicarboxylic compound comprising at least one ethylenic unsaturation in the alpha position of one of the carboxyl groups. Also disclosed are middle distillate compositions having a distillation range from 150.degree. to 450.degree. C. and comprising a minor proportion, preferably from 0.001 to 2% by weight, of at least one of the polymers defined hereinabove.
    Type: Grant
    Filed: February 6, 1989
    Date of Patent: August 6, 1991
    Assignees: Institut Francais du Petrole, Elf France
    Inventors: Jacques Garapon, Remi Touet, Bernard Damin, Beatrice Debled
  • Patent number: 5032489
    Abstract: An optically functional element comprising an aromatic vinylene sulfide polymer as an optically changing element is disclosed. The optically functional element undergoes optical changes with low energy at a high rate to provide high contrast before and after the optical changes.
    Type: Grant
    Filed: February 26, 1990
    Date of Patent: July 16, 1991
    Assignees: Eiichi Kobayashi, Mitsubishi Petrochemical Co., Ltd.
    Inventors: Eiichi Kobayashi, Toyoshi Ohashi, Mitsutaka Miyabayashi
  • Patent number: 5013821
    Abstract: Biodegradable ortho ester polymers based on mono- and poly-thiols are provided that are useful for making biodegradable sustained release agent dispensers and which contain at least one of the mer units (I), (II), (III) or (IV) ##STR1## wherein X is a quadrivalent organic grouping, A and B are independently selected from the group consisting of hydrogen and lower alkyl, and R is hydrocarbyl or oxyhydrocarbyl of 1 to 14 carbon atoms, if oxyhydrocarbyl, containing 1 to 4 oxy groups, and may be either aliphatic or aryl, unsubstituted or substituted with one or more lower alkyl, amino, nitro or halogen moieties.
    Type: Grant
    Filed: June 15, 1989
    Date of Patent: May 7, 1991
    Assignee: Pharmaceutical Delivery Systems, Inc.
    Inventors: Jorge Heller, Steve Y. W. Ng, Donald W. H. Penhale
  • Patent number: 4918159
    Abstract: Novel styrene-based polymers and a process for efficient production thereof are disclosed. The styrene-based polymers have a branching nucleus represented by the general formula: R(S).sub.k or R(A-S).sub.k (wherein all the symbols are as defined in the appended claims), and have a sulfur content of 6 to 550 ppm, a weight average molecular weight of 450,000 to 1,300,000, and a weight average molecular weight/number average molecular weight (Mw/Mn) ratio of 2:1 to 15:1. The styrene-based polymers are greatly improved in impact resistance while maintaining sufficiently high fluidity and moldability and thus when injection or extrusion molded, can provide moldings having an excellent mechanical strength.
    Type: Grant
    Filed: August 29, 1988
    Date of Patent: April 17, 1990
    Assignee: Idemitsu Petrochemical Co., Ltd.
    Inventors: Shinichi Nakamura, Hideo Teshima, Eiichi Terada
  • Patent number: 4835249
    Abstract: A process for making certain polyimides involves dissolving substantially equimolar amounts of an aromatic dianhydride and an organic diamine in a high-boiling, aprotic solvent, heating the reaction solution to form an insoluble polyimide prepolymer and to distill out water of reaction, separating the solid polyimide prepolymer and melt polymerizing the polyimide prepolymer to form the desired polyimide.
    Type: Grant
    Filed: December 31, 1986
    Date of Patent: May 30, 1989
    Assignee: General Electric Company
    Inventors: Patrick E. Gallagher, Ronald A. Greenberg
  • Patent number: 4818804
    Abstract: A novel polycondensable macaronmonomer of the formula: ##STR1## wherein R is OH or COOH, R.sup.1, R.sup.2 and R.sup.3 are the same or different and are each a single bond or an alkylene having 1 to 4 carbon atoms, R.sup.4 is hydrogen atom or an alkyl having 1 to 4 carbon atoms, R.sup.5 is hydrogen atom or methyl, X is an alkyloxycarbonyl having 2 to 15 carbon atoms, a sustituted alkyloxycarbonyl having 2 to 15 carbon atoms in the alkyloxycarbonyl moiety, a cycloalkyloxycarbonyl having 3 to 7 carbon atoms in the cycloalkyl moiety, or phenyl, and n is an integer of from 1 to 1.times.10.sup.4, which is useful as an intermediate for the prodcution of a polymer having comb-shape structure useful as an adhesive, adhesion improver, caompatibilizing agent, surfactant, etc.
    Type: Grant
    Filed: August 28, 1987
    Date of Patent: April 4, 1989
    Assignee: Sunstar Giken Kabushiki Kaisha
    Inventors: Akira Kuriyama, Mikiko Yamaguchi
  • 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: 4766195
    Abstract: Polymer or copolymer having a chain carrying terminal and/or side-chain groups: ##STR1## in which R is an H or a C.sub.2 to C.sub.12 alkyl, m is 0 to 6, n is 1 to 10 and p is 1 to 10, one, some or all of the p double bonds being saturatable by an active group.
    Type: Grant
    Filed: December 15, 1986
    Date of Patent: August 23, 1988
    Assignee: Societe Nationale Elf Aquitaine
    Inventor: Yves Labat
  • Patent number: RE33377
    Abstract: Sulfur-modified polychloroprene in alkaline aqueous emulsion is prepared by incorporating one or more organic polysulfides which act as peptizing agents during the polymerization of the chloroprene. The sulfur-modified polychloroprenes obtained have stable viscosities.
    Type: Grant
    Filed: October 20, 1988
    Date of Patent: October 9, 1990
    Assignee: Distugil
    Inventors: Paul Branlard, Jean-Pierre Merle