Polymer Mixed With Unsaturated Reactant Containing Aryl Ring Patents (Class 525/40)
  • Patent number: 11013231
    Abstract: Stabilized liquid cyclopropane compositions are provided which compromise flowable, non-aqueous dispersion concentrates comprising a) a continuous substantially water-immiscible liquid phase and b) a dispersed solid phase comprising cured polymer particles prepared from a polymerizable thermoset resin which particles contain at least one cylcopropene complex, optionally a non-porous particulate mineral, and optionally a non-cross-linkable mobile chemical distributed therein, and wherein the outside surfaces of the particles comprise a colloidal solid material. The compositions of the invention can be used directly or with dilution to combat pests or as plant growth regulators.
    Type: Grant
    Filed: January 31, 2019
    Date of Patent: May 25, 2021
    Assignee: SYNGENTA PARTICIPATIONS AG
    Inventors: Jeffrey David Fowler, Sejong Kim
  • Patent number: 10259201
    Abstract: The invention relates to a composite comprising (i) a plastics component or (ii) a semifinished plastics product with a protective layer system, where the protective layer system comprises a plastics film and an organosilicon plasma polymer layer, the organosilicon plasma polymer layer is arranged between the (i) plastics component or the (ii) semifinished plastics product and the plastics film and, after the hardening of the (i) plastics component or of the (ii) semifinished plastics product, the organosilicon plasma polymer layer adheres more securely to the plastics film than to the (i) plastics component or the (ii) semifinished plastics product.
    Type: Grant
    Filed: April 26, 2013
    Date of Patent: April 16, 2019
    Assignee: Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V.
    Inventors: Klaus-Dieter Vissing, Matthias Ott, Gregor Grassl
  • Patent number: 8790762
    Abstract: The present invention relates to an unsaturated polyester resin comprising itaconate esters as reactive unsaturations, wherein the acid value of the resin is in the range of from 25 to 125 and the molar ratio of hydroxyl end groups and carboxylic acid end groups is in the range of from 0.33 to 3. In one embodiment, the molar ratio of hydroxyl end groups and carboxylic acid end groups is in the range of from 0.33 to 0.9. In another embodiment, the molar ratio of hydroxyl end groups and carboxylic acid end groups is in the range of from 1.1 to 3.
    Type: Grant
    Filed: March 24, 2010
    Date of Patent: July 29, 2014
    Assignee: DSM IP Assets B.V.
    Inventors: Marian Henryk Szkudlarek, Johan Franz Gradus Antonius Jansen, Silvana Rensina Antonnietta Di Silvestre, Stefanus Jacobus Duyvestijn
  • Patent number: 8263303
    Abstract: A method for producing a colored resin particle dispersion liquid comprises: polycondensing a polyester-forming monomer in a nonaqueous solvent to produce an unsaturated polyester; graft-polymerizing an ethylenic unsaturated monomer to the unsaturated polyester in a nonaqueous solvent to produce a modified polyester resin; and dispersing a colorant and the modified polyester resin to produce a colored resin particle dispersion liquid, the polycondensing and the graft-polymerizing being carried out at a temperature of 150° C. or less.
    Type: Grant
    Filed: August 10, 2006
    Date of Patent: September 11, 2012
    Assignee: Fuji Xerox Co., Ltd.
    Inventors: Hirotaka Matsuoka, Yuki Sasaki, Satoshi Hiraoka, Fumiaki Mera, Yasuo Matsumura
  • Publication number: 20120121841
    Abstract: The present invention relates to an unsaturated polyester resin comprising itaconate esters as reactive unsaturations, wherein the acid value of the resin is in the range of from 25 to 125 and the molar ratio of hydroxyl end groups and carboxylic acid end groups is in the range of from 0.33 to 3. In one embodiment, the molar ratio of hydroxyl end groups and carboxylic acid end groups is in the range of from 0.33 to 0.9. In another embodiment, the molar ratio of hydroxyl end groups and carboxylic acid end groups is in the range of from 1.1 to 3.
    Type: Application
    Filed: March 24, 2010
    Publication date: May 17, 2012
    Applicant: DSM IP Assets B.V.
    Inventors: Marian Henryk Szkudlarek, Johan Franz Gradus Antonius Jansen, Silvana Rensina Antonnietta Di Silvestre, Stefanus Jacobus Duyvestijn
  • Patent number: 7803415
    Abstract: A composition for coating food cans is disclosed. The composition comprises a polyester, an acrylic copolymer and a crosslinker; the polyester and acrylic copolymer have been compatibilized in some way, such as through graft copolymerization. Methods for compatibilizing acrylics and polyesters are also disclosed as are methods for coating cans using compositions comprising acrylic and polyesters.
    Type: Grant
    Filed: September 27, 2007
    Date of Patent: September 28, 2010
    Assignee: PPG Industries Ohio, Inc.
    Inventors: Laura Kiefer-Liptak, John M. Dudik, Ronald R. Ambrose, Kevin C. Olson, Padmanabhan Sundararaman
  • Patent number: 7745508
    Abstract: A composition for coating food cans is disclosed. The composition comprises a polyester, an acrylic copolymer and a crosslinker; the polyester and acrylic copolymer have been compatibilized in some way, such as through graft copolymerization. Methods for compatibilizing acrylics and polyesters are also disclosed as are methods for coating cans using compositions comprising acrylic and polyesters.
    Type: Grant
    Filed: August 30, 2002
    Date of Patent: June 29, 2010
    Assignee: PPG Industries Ohio, Inc.
    Inventors: Laura Kiefer-Liptak, John M. Dudik, Ronald R. Ambrose, Kevin C. Olson, Padmanabhan Sundararaman
  • Patent number: 7112627
    Abstract: A curing low dielectric loss tangent film using a low dielectric loss tangent composition containing a polyfunctional styrene compound having excellent dielectric characteristics, and a wiring film using the same as an insulating layer are provided. The low dielectric loss tangent film contains a high molecular weight material and a crosslinking ingredient with a weight average molecular weight of 1000 or less having a plurality of styrene groups shown by the following general formula: (where R represents a hydrocarbon skeleton, R1, which may be identical or different with each other, represents a hydrogen atom or a hydrocarbon group of 1 to 20 carbon atoms, R2, R3 and R4, which may be identical or different with each other, each represents a hydrogen atom or an alkyl group of 1 to 6 carbon atoms, m represents an integer of 1 to 4, and n represents an integer of 2 or greater).
    Type: Grant
    Filed: March 12, 2003
    Date of Patent: September 26, 2006
    Assignee: Hitachi, Ltd.
    Inventors: Satoru Amou, Shinji Yamada, Takao Ishikawa, Akira Nagai, Masatoshi Sugimasa
  • Patent number: 6617395
    Abstract: A low tack, low VOC gel coat is disclosed comprising a unsaturated polyester resin derived from maleic anhydride and up to about 30% of an organic solvent. The resin is characterized by: a viscosity of less than or equal to about 1750 cp at 70% NVM in styrene; a glass transition temperature greater than or equal to about 11° C.; and a weight average molecular weight less than or equal to about 6,050. A process for making such a gel coat is also disclosed.
    Type: Grant
    Filed: April 8, 2002
    Date of Patent: September 9, 2003
    Assignee: Cook Composites & Polymers Co.
    Inventors: Ming Yang Zhao, L. Scott Crump, Chih-Pin Hsu, Erwoan Pezron
  • Patent number: 6521703
    Abstract: A curable resin composition includes an unsaturated polyester, an alkenyl aromatic compound, and a capped poly(arylene ether). The composition is suitable for low temperature curing and exhibits reduced curing shrinkage and reduced brittleness.
    Type: Grant
    Filed: January 17, 2001
    Date of Patent: February 18, 2003
    Assignee: General Electric Company
    Inventors: Kenneth Paul Zarnoch, Hua Guo, Herbert Shin-I Chao
  • Patent number: 6235851
    Abstract: A compound shown by the following formula: wherein each of R1a, R2a, R3a and R4a represents a substituent selected from a non-reactive atom, a non-reactive group, a hydroxyl group and an amino group, and at least two members selected from R1a, R2a, R3a and R4a are a hydroxyl group, a carboxyl group or an amino group; is subjected to an esterification reaction or an amidation reaction with a polymerizable unsaturated compound (e.g., an alcohol, a carboxylic acid, an amine) in the presence of a catalyst comprising an element selected from the Group 3 elements, such as a samarium compound, to obtain a polymerizable adamantane derivative having at least one polymerizable unsaturated group in high yield.
    Type: Grant
    Filed: January 11, 1999
    Date of Patent: May 22, 2001
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Yasutaka Ishii, Tatsuya Nakano, Naruhisa Hirai
  • Patent number: 5973020
    Abstract: The present invention relates to a photoinitiator composition that can be used to initiate polymerization upon exposure to radiation. The said composition includes both a composition which yields cations upon exposure to actinic radiation, such as an iodonium borate initiator and a stabilizing amino agent. The amino agent is a secondary or tertiary amine having the general formula (VIII), a sterically arranged cyclic amine having the general formula (IX), or an amine consisting of groups that have the general formulas (VIII) and (IX) and that are interconnected. ##STR1## The compositions are particularly useful when used in conjunction with polyorganosiloxane monomers and when exposed to ultraviolet radiation.
    Type: Grant
    Filed: January 6, 1998
    Date of Patent: October 26, 1999
    Assignee: Rhodia Inc.
    Inventors: Stuart R. Kerr, III, Reeshemah L. Beaty
  • Patent number: 5599875
    Abstract: Coating compositions and processes for coating wood and wood materials are described. The compositions comprise a first component comprising at least one reactive thinner and at least one unsaturated polyester, and a second component comprising a curing catalyst. The unsaturated polyester of the first component is the reaction product of: (a) a mixture of at least one saturated aliphatic dicarboxylic acid with 6 to 10 carbon atoms and at least one ethylenically unsaturated aliphatic dicarboxylic acid selected from maleic acid, fumaric acid, itaconic acid, citraconic acid, and mixtures thereof; (b) a diol component consisting of at least one of 1,4-dimethylolcyclohexane and substituted dimethylolcyclohexanes, with up to 50 mol % monomeric or oligomeric glycol, based on total moles of the diol component; and (c) up to 10 mol % of a polyol, based on total moles of polyester reactants. The compositions and processes of the invention result in coatings with improved hardness and aged cold crack resistance.
    Type: Grant
    Filed: August 28, 1995
    Date of Patent: February 4, 1997
    Assignee: BASF Lacke + Farben, AG
    Inventors: Karl-Dieter Depping, Horst Hintze-Bruning
  • Patent number: 5567767
    Abstract: A laminating resin is made from (1) an unsaturated polyester resin, (2) a diacrylate or dimethacrylate of alkoxylated bisphenol-A, and (3) vinyl toluene. The resin requires no styrene to achieve excellent laminating resin properties, and is significantly inhibited from emitting volatiles during use.
    Type: Grant
    Filed: December 11, 1995
    Date of Patent: October 22, 1996
    Assignee: Aristech Chemical Corporation
    Inventors: Thomas W. Smeal, George L. Brownell
  • Patent number: 5567766
    Abstract: A laminating resin is made from (1) an unsaturated polyester resin, (2) a diacrylate or dimethacrylate of alkoxylated bisphenol-A, and (3) styrene, divinyl benzene or a combination thereof. The resin achieves excellent laminating resin properties, and is significantly inhibited from emitting volatiles during use.
    Type: Grant
    Filed: December 11, 1995
    Date of Patent: October 22, 1996
    Assignee: Aristech Chemical Corporation
    Inventors: Thomas W. Smeal, George L. Brownell
  • Patent number: 5428080
    Abstract: A heat reservoir device for maintaining a comestible at a desired consumption temperature consisting essentially of a shaped reinforced thermoset polyester resin, preferably one made by reacting isophthalic acid, propylene glycol, and fumaric acid to form the unsaturated polyester and then forming a solution thereof in a vinyl monomer. The invention also include the method of maintaining a comestible at a desired temperature using such device.
    Type: Grant
    Filed: March 11, 1994
    Date of Patent: June 27, 1995
    Assignee: Plastics Manufacturing Company
    Inventor: Michael L. Miller
  • Patent number: 5410000
    Abstract: Copolyester compositions are provided which comprise the reaction product of at least one straight chain, branched, or cycloaliphatic C.sub.2 -C.sub.10 alkane diol or a chemical equivalent thereof, a mixture of at least two cycloaliphatic diacids or chemical equivalents thereof, the mixture comprising predominantly a trans-enantiomer, and at least one aromatic diacid or a chemical equivalent thereof. These copolyesters have superior ductility to the homopolymers of the diol component and either of the diacid components.
    Type: Grant
    Filed: August 18, 1994
    Date of Patent: April 25, 1995
    Assignee: General Electric Company
    Inventor: Willem F. H. Borman
  • Patent number: 5380793
    Abstract: This invention is a low cost styrene-soluble unsaturated polyester resin made using recycled or virgin polyethylene terephthalate. The PET is first glycolyzed using inexpensive glycols and then reacted with maleic anhydride and dicyclopentadiene, forming polyesters containing cyclopentadiene added by Diels-Alder reaction and/or norbornyl-terminated polyesters.
    Type: Grant
    Filed: July 13, 1993
    Date of Patent: January 10, 1995
    Assignee: Ashland Oil, Inc.
    Inventor: Timothy P. Pepper
  • Patent number: 5254642
    Abstract: The present invention is based on the unexpected discovery that the low profile additives (LPA) disclosed in U.S. Pat. No. 5,116,917 provide effective shrinkage control when used with various blends of vinyl ester and polyester resin systems. This LPA is unique in that its low profile efficiency is not affected by the different reactivities displayed by blends of vinyl ester resin and polyester resin at different blend ratios. This LPA is equally effective in formulations of all vinyl ester resin, all polyester resin, or any combination of such two resins. The present invention, then, is directed to a thermosettable resinous composition of between about 0 and 95 wt-% of a thermosettable vinyl ester resin; between about 5 and 100 wt-% of a thermosettable polyester resin; and between about 5 and 40 wt-% of a low profile additive comprising a non-gelling, saturated polyester formed from dibasic acid and an EO/PO block copolymer having an EO/PO molar ratio ranging from about 0.1 to 0.
    Type: Grant
    Filed: September 12, 1992
    Date of Patent: October 19, 1993
    Assignee: Ashland Oil, Inc.
    Inventors: Ken K. Chang, Timothy A. Tufts
  • Patent number: 5171784
    Abstract: Novel phosphorylated compositions of a vinyl chloride copolymer or terpolymer, a phenoxy resin, a hydroxyalkyl acrylate or methacrylatelactone adduct or a reaction product of a normally solid pendant-hydroxyl-containing thermoplastic polymer having at least 8 hydroxyl groups per molecular chain and an adduct which is the product of either a hydroxylalkyl acrylate or methacrylate or a lactone-acrylate adduct and an organic diisocyanate having improved dispersion characteristics suitable for use in applications such as magnetic recording media.
    Type: Grant
    Filed: January 17, 1992
    Date of Patent: December 15, 1992
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Ismael Colon, Charles B. Mallon, Robert N. Johnson
  • Patent number: 5028456
    Abstract: A curable polyester composition having improved properties is described, and the curable polyester composition comprises:(A) at least one unsaturated polyester resin;(B) at least one hydrocarbon monomer copolymerizable with the polyester; and(C) at least one aryl sulfonamide-aldehyde resin.When the curable polyester composition is to be used as a plastic body filler, the curable polyester composition generally will be modified to include (D) at least one inorganic filler which may comprise a mixture of an inorganic powder and inorganic hollow microspheres.The curable polyester resin compositions of the invention are useful as plastic body fillers for repairing metal surfaces, and the curable compositions have been found to be particularly useful and advantageous as plastic body fillers for galvanized steel.
    Type: Grant
    Filed: September 28, 1990
    Date of Patent: July 2, 1991
    Assignee: Oatey Company
    Inventor: Paul E. Naton
  • Patent number: 5002983
    Abstract: A polyarylene sulfide resin composition comprising a composition obtainable by a reaction of a polymer composition comprising(A) 100 parts by weight of a polyarylene sulfide resin,(B) 0.1 to 40 parts by weight of a monomer having one or more ethylenic unsaturated bonds and(C) 0 to 40 parts by weight of an unsaturated polyester. In the polyarylene sulfide resin composition of the present invention, a polymer produced by polymerization of the monomer or the monomer and unsaturated polyester, as compared with a resin composition wherein said polymer is simply blended, is in a state wherein it is uniformly mixed with the polyarylene sulfide resin and if necessary a filler. In other words, said polymer is uniformly dispersed in and mixed with the polyarylene sulfide resin to such a degree that the composition shows no phase separation even if it is passed through molding processes such as extrusion molding, injection molding, etc. carried out under normal conditions.
    Type: Grant
    Filed: February 7, 1990
    Date of Patent: March 26, 1991
    Assignee: Mitsubishi Rayon Co., Ltd.
    Inventors: Akira Nakata, Naoki Yamamoto, Hiroshi Mori, Takuya Ueno
  • Patent number: 4997866
    Abstract: A polyarylene sulfide resin composition comprising a resin composition obtainable by polymerizing 40 to 0.1 part by weight of an unsaturated polyester and 0.01 to 30 parts by weight of a monomer having one or more ethylenic unsaturated bonds in the presence of 100 parts by weight of a composition comprising 1 to 99 wt. % of a polyarylene sulfide resin and 99 to 1 wt. % of a thermoplastic polyester. Since the polyarylene sulfide resin composition of the present invention is in a state wherein the polyarylene sulfide resin and thermoplastic polyester are uniformly mixed, the constituent components are uniformly dispersed and mixed to such a degree that the composition shows no phase separation even if it is passed through molding processes such as extrusion molding, injection molding, etc. carried out under normal conditions.
    Type: Grant
    Filed: February 16, 1990
    Date of Patent: March 5, 1991
    Assignee: Mitsubishi Rayon Co., Ltd.
    Inventors: Akira Nakata, Naoki Yamamoto, Hiroshi Mori, Takuya Ueno
  • Patent number: 4983668
    Abstract: Particle size, swelling, and other characteristics of unsaturated polyester beads are controlled in a suspension polymerization system to make beads suitable for use as fillers in molding and forming. Process steps include degassing prior to polymerization, positive pressure during polymerization, and washing to remove suspending agent.
    Type: Grant
    Filed: November 25, 1987
    Date of Patent: January 8, 1991
    Assignee: Aristech Chemical Corporation
    Inventors: Louis A. Cutter, Richard A. Ganger, John J. Godfrey
  • Patent number: 4977240
    Abstract: A peroxide curing agent composition containing 20-90% of an unsaturated alkyd diluent which is fluid at room temperature, is disclosed. The curing agent is useful for the curing of unsaturated polyesters and eliminates the problem of the bleeding of harmful phthalate diluents from such cured polyesters, while providing excellent stability of the diluted peroxide.
    Type: Grant
    Filed: November 7, 1989
    Date of Patent: December 11, 1990
    Assignee: Kayaku Akzo Corporation
    Inventor: Akio Ishiwatari
  • Patent number: 4921883
    Abstract: Unsaturated polyester resins having an acid number of from 0 to 50 and a hydroxyl number of from 10 to 150 which are composed of 0.6 to 0.8 moles of groups derived from maleic and/or fumaric acid, 0.2 to 0.4 moles of groups derived from norbornene dicarboxylic acid, 0.6 to 0.8 moles of groups derived from ethylene and/or propylene glycol, 0.2 to 0.4 moles of groups derived from diethylene glycol, 0.1 to 0.2 moles of groups derived from benzylalcohol and/or benzoic acid and 0 to 0.2 moles of groups derived from other alcohols, a process for their manufacture by a solvent-free or azeotropic esterification of said monomers and compositions which can be cured under influence of UV radiation, containing from 40 to 80 parts by weight of said polyester resins, from 20 to 60 parts by weight of styrene from 0.5 to 5 parts by weight of at least one photoinitiator and optionally known auxiliary agents and additives.
    Type: Grant
    Filed: March 18, 1988
    Date of Patent: May 1, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Jurgen Meixner, Wolfgang Kremer, Manfred Muller
  • Patent number: 4837270
    Abstract: Thermosetting and cold-setting unsaturated polyester resin molding compounds which contain only one saturated polyester as LP additive and which do not show LP drift under usual storage conditions, are provided. Molded articles molded therefrom exhibit low shrinking and a perfect surface.
    Type: Grant
    Filed: June 12, 1987
    Date of Patent: June 6, 1989
    Assignee: Huels Aktiengesellschaft
    Inventors: Horst Kraemer, Hartmut Rohmer, Johannes Stawowy
  • Patent number: 4835213
    Abstract: A process for producing a lactone polymer which comprises reacting an ester compound synthesized from an alcohol and an acid or acid anhydride thereof with a lactone and a ring-opening polymerization initiator without being accompanied by condensation. The thus produced lactone polymer is effective for preventing shrinkage of thermosetting resins, particularly unsaturated polyester resins.
    Type: Grant
    Filed: February 26, 1987
    Date of Patent: May 30, 1989
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Takaaki Murai, Shoji Watanabe, Kimio Inoue, Tomohisa Isobe, Naoki Nakashima, Takuya Miho, Yoshiyuki Ikemoto
  • Patent number: 4698411
    Abstract: An unsaturated polyester resin syrup containing styrene monomer in which styrene volatilization is suppressed using a substituted succinic acid or substituted succinic anhydride.
    Type: Grant
    Filed: April 30, 1986
    Date of Patent: October 6, 1987
    Assignee: Phillips Petroleum Company
    Inventors: H. Wayne Hill, Jr., Michael D. Cliffton
  • Patent number: 4656224
    Abstract: Compositions consisting essentially of thermoset polymers prepared by copolymerizing a solution of an iodine containing, crosslinkable, unsaturated polyester resin dissolved in a vinyl monomer are disclosed. These compositions have been found to be useful as radiopaque agents and in the manufacture of radiopaque, flame retardant articles.
    Type: Grant
    Filed: June 23, 1986
    Date of Patent: April 7, 1987
    Assignee: The Dow Chemical Company
    Inventor: Eric R. Larsen
  • Patent number: 4595725
    Abstract: Certain unsaturated polyester resins, so-called soft resins, having certain parameters are suitable for the production of hardened moldings of high elasticity.
    Type: Grant
    Filed: March 15, 1985
    Date of Patent: June 17, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Bernhard Hess, Bert Brassat, Bernhard Peltzer
  • Patent number: 4524177
    Abstract: 1,4-Dihydroxynaphthalene, iron compounds and optionally tertiary arylamines prove to be a highly active accelerator/stabilizer system for peroxide-catalyzed ethylenically unsaturated hardenable compounds.
    Type: Grant
    Filed: November 23, 1983
    Date of Patent: June 18, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Werner Kloker, Klaus Kraft
  • Patent number: 4507432
    Abstract: In curing an unsaturated polyester resin in the presence of an organic peroxide added thereto, 4-methyl-2,4-diphenyl-pentene-1 is added to the mixture of the unsaturated polyester resin with the organic peroxide to enhance the curing properties.
    Type: Grant
    Filed: October 24, 1983
    Date of Patent: March 26, 1985
    Assignee: Nippon Oil & Fats Co., Ltd.
    Inventors: Shigeki Banno, Takeshi Komai
  • Patent number: 4420587
    Abstract: Phosphonopolyester oligomers are prepared from hydroxyalkylated 2,2',-bis(3-allylphenyl-4-hydroxy) alkanes and phosphonyl dihalides. The oligomers are useful in the preparation of polyester resins, epoxy resins, and polyurethanes.
    Type: Grant
    Filed: September 27, 1982
    Date of Patent: December 13, 1983
    Assignee: The Dow Chemical Company
    Inventor: Robert E. Hefner, Jr.
  • Patent number: 4419487
    Abstract: Unsaturated polyester resins are rendered less brittle without significantly deteriorating other physical properties by reacting therewith 0.1 to 25 parts of a carboxyl terminated reactive liquid polymer, preferably poly(butadiene-acrylonitrile), per 100 parts of the polyester resin.
    Type: Grant
    Filed: April 22, 1982
    Date of Patent: December 6, 1983
    Assignee: The B. F. Goodrich Company
    Inventor: Eugene H. Rowe
  • Patent number: 4370447
    Abstract: An unsaturated polyester was obtained by reacting a polyhydric alcohol with a mixture of an unsaturated polybasic acid and a specific saturated dibasic acid represented by the formula: ##STR1## or the formula: ##STR2## wherein, R.sub.1 to R.sub.10 are each hydrogen or alkyl, R' to R"" are the same or different and each represent hydrogen or ester-exchangeable alkyl, m is 1 or 2, and n is zero or 1. The compositions comprising this polyester and an aromatic vinyl monomer, when hardened in the presence of a catalyst, exhibit a lower shrinkage during the hardening and give molded products with improved resistance to alkalis and to boiling water.
    Type: Grant
    Filed: March 11, 1981
    Date of Patent: January 25, 1983
    Assignee: Japan Synthetic Rubber Co., Ltd.
    Inventors: Katuhiro Ishikawa, Ryotaro Ohno, Masatoshi Arakawa
  • Patent number: 4343932
    Abstract: The invention provides unsaturated polyester compositions which can be cured to form flexible objects, which compositions comprise terminal 1,2-alkene dicarboxylic acid in an amount of 1-25, preferably 3-15 mol-percent, calculated on the total amount of dicarboxylic acid, and 1-8, preferably 2.5-6 mol-percent of the dicarboxylic acids in the chain of the polyester consists of trans-1,2-alkene dicarboxylic acid.
    Type: Grant
    Filed: December 10, 1980
    Date of Patent: August 10, 1982
    Assignee: Internationale Octrooi Maatschappij "Octropa" BV
    Inventors: Jacob J. Prooi, Waltherus J. Sep, Wilhelmina Westerhof
  • Patent number: 4334035
    Abstract: An unsaturated polyester resin composition comprising (A) an unsaturated polyester alkyd prepared by condensing all or at least 30 mol% of 1,2-butanediol as a polyhydric alcohol component, all or part of phthalic anhydride as a saturated polybasic acid component, and an unsaturated polybasic acid component, and (B) an unsaturated monomer copolymerizable with component (A), the amount of component (B) being 20 to 55 parts by weight based on 100 parts by weight of component (A) is disclosed. The thus-formed unsaturated polyester resin composition is of low viscosity and is easy in filling with glass fibers, pigments, inorganic fillers, etc. Further, it has such advantages that the smell of the unsaturated monomer is low and that the influence against human beings due to evaporation of the unsaturated monomer can be reduced.
    Type: Grant
    Filed: March 19, 1981
    Date of Patent: June 8, 1982
    Assignee: Mitsubishi Petrochemical Co., Ltd.
    Inventors: Taketoshi Fujita, Yasuyuki Ohgi, Yousui Nemoto
  • Patent number: 4298711
    Abstract: A low shrink unsaturated polyester based upon propylene glycol terephthalate reacted with a dibasic acid or anhydrides thereof and glycols.
    Type: Grant
    Filed: April 9, 1980
    Date of Patent: November 3, 1981
    Assignee: Cargill Incorporated
    Inventors: Thomas J. Moulson, John E. Greenzweig
  • Patent number: 4294751
    Abstract: This invention involves a curable molding composition comprising a mixture of (a) a polyester of the following formula: ##STR1## wherein n has an average value between about 1.
    Type: Grant
    Filed: April 14, 1980
    Date of Patent: October 13, 1981
    Assignee: Union Carbide Corporation
    Inventor: Hugh C. Gardner
  • Patent number: 4293686
    Abstract: This invention comprises a polymerizable composition of a liquid mixture of (a) an unsaturated polyester, (b) a half ester characterized by the following empirical formula: ##STR1## wherein n is a number having an average value of about 1.5 to less than about 4, m is equal to the free valence of A less the average value of n, A is the hydroxyl-free residue of an organic polyol which contained from 2 to 4, inclusive, hydroxyl groups, OH, in formula (I), (c) maleic anhydride and (d) an ethylenically unsaturated monomer. This composition is suitable for use in the manufacture of fiber reinforced plastic compositions.
    Type: Grant
    Filed: April 18, 1980
    Date of Patent: October 6, 1981
    Assignee: Union Carbide Corporation
    Inventor: Hugh C. Gardner
  • Patent number: 4290938
    Abstract: A thermosetting injection molding compound comprising a specific crystalline unsaturated polyester comprising (A) a crystalline unsaturated polyester of terephthalic acid/fumaric acid=5/5-1/9 by mol (acid component) and 1,4-butanediol/other glycol=7/3-10/0 (glycol component) and (B) a styrene type monomer and/or allyl type monomer, and having specific ranges of a viscosity, a melting point and an acid value, said crystalline unsaturated polyester resin being admixed with (C) a glass fiber and (D) other additives in a specific ratio.
    Type: Grant
    Filed: January 4, 1980
    Date of Patent: September 22, 1981
    Assignee: Toyo Boseki Kabushiki Kaisha Co., Ltd.
    Inventors: Hideo Miyake, Junichi Sakamoto, Masakazu Sawaki, Mamoru Hara
  • Patent number: 4281074
    Abstract: In the first stage a mixture of a crude diene adduct of 2-naphthol with maleic anhydride is polycondensed at a temperature within the range from 180.degree. to 200.degree. C. with excess glycol or with a dihydric aromatic alcohol, from 0.1 to 3 moles of the alcohol being used per 1 mole of the adduct. In the second stage, the thus obtained product is condensed at a temperature within the range from 160.degree. to 210.degree. C. with an unsaturated acid or the anhydride thereof and with the addition of an equimolar quantity (with respect to the acid or its anhydride) of glycol and/or a dihydric aromatic alcohol. The resulting product is then dissolved in styrene and copolymerized to obtain a cured polyester resin. Propylene glycol, diethylene glycol, dipropylene glycol or butylene glycol may be used as the glycol. The C.sub.2 or C.sub.
    Type: Grant
    Filed: February 26, 1980
    Date of Patent: July 28, 1981
    Assignee: Polska Akademia Nauk, Zaklad Polimerow
    Inventors: Zbigniew Jedlinski, Antoni Kotas, Boleslaw Ryndak, Stanislaw Mazur, Jan Czarnecki, Mieczyslaw Walkowicz, Stanislaw Jedlinski
  • Patent number: 4269745
    Abstract: An unsaturated polyester resin composition includes small quantities of hydrocarbon wax and small quantities of an unsaturated alkyd resin formed from the reaction of linseed oil fatty acids, alpha, beta-ethylenically unsaturated dicarboxylic acid and glycol. Styrene volatilization from the resulting system is reduced. The secondary bonding properties of the resulting resin composition are not adversely affected.
    Type: Grant
    Filed: April 4, 1980
    Date of Patent: May 26, 1981
    Assignee: Freeman Chemical Corporation
    Inventor: Dennis J. Neumann
  • Patent number: 4268431
    Abstract: A colorant-thickener dispersion for unsaturated polyester resin compositions comprises(a) 20% to 50% by weight of a thickener comprising a Group II-A metal oxide or hydroxide,(b) 5% to 20% by weight of a pigment component, and(c) 30% to 75% by weight of an unsaturated polyester vehicle that comprises(1) 50% to 100% by weight of at least one unsaturated polyester that is the product of the reaction of a dicarboxylic acid component containing 80 to 90 mole % of at least one unsaturated aliphatic dicarboxylic acid having 4 to 8 carbon atoms and 10 to 20 mole % of at least one saturated aromatic dicarboxylic acid with an alcohol component containing 40 to 60 mole % of at least one glycol having 2 to 6 carbon atoms and 40 to 60 mole % of at least one monohydric alcohol having 6 to 12 carbon atoms, in the amount of 0.4 mole to 0.
    Type: Grant
    Filed: June 1, 1979
    Date of Patent: May 19, 1981
    Assignee: Tenneco Chemicals, Inc.
    Inventors: Martin L. Feldman, James T. De Groff
  • Patent number: 4246367
    Abstract: The invention disclosed is for a method of preparing unsaturated polyester resins containing high amounts of dicyclopentadiene. These polyester resins are useful in curable liquid compositions containing them together with a monomeric copolymerizable component. Such compositions may be used at ambient or elevated temperature, in casting, laminating or molding techniques known to the polyester resin art.
    Type: Grant
    Filed: September 24, 1979
    Date of Patent: January 20, 1981
    Assignee: United States Steel Corporation
    Inventor: Omer E. Curtis, Jr.
  • Patent number: 4243763
    Abstract: Tertiary aromatic amines derived from aminoglutethimide or para-aminophenylacetic acid act as accelerators for the peroxide catalyzed polymerization of acrylic resins, especially methacrylates, acrylates and unsaturated polyesters. The amines are characterized by good hardening, strength, color and toxicity characteristics, and are thereby particularly suited for use in the filling and restoration of human teeth and the cementing of bone.
    Type: Grant
    Filed: March 10, 1978
    Date of Patent: January 6, 1981
    Assignee: American Dental Association Health Foundation
    Inventor: Harold Argentar
  • Patent number: 4233413
    Abstract: A resin composition comprising (A) 25 to 45 parts by weight of an unsaturated polyester having special structure, (B) 40 to 60 parts by weight of polymerizable monomer such as styrene, and (C) 4.5 to 15 parts by weight of a polystyrene, has low shrink properties and excellent electrical properties when molded, particularly by casting.
    Type: Grant
    Filed: November 28, 1978
    Date of Patent: November 11, 1980
    Assignee: Hitachi Chemical Company, Ltd.
    Inventors: Noboru Monma, Iwao Maekawa, Tutomu Sarudate, Hidetaka Sato, Isao Uchigasaki
  • Patent number: 4228251
    Abstract: A resin composition which comprises (A) 50 to 90 parts by weight of an unsaturated ester oligomer produced by reacting a glycol, hydroxylated dicyclopentadiene, and at least one unsaturated dibasic acid or anhydride thereof until an acid value of less than 40, (B) 50 to 10 parts by weight of one or more polymerizable monomers, and (C) 3 to 15 parts by weight of polystyrene based on 100 parts by weight of the total of the components (A) and (B), can give molded articles having low shrink properties and improved color shading, cracks, etc.
    Type: Grant
    Filed: November 30, 1978
    Date of Patent: October 14, 1980
    Assignee: Hitachi Chemical Company, Ltd.
    Inventors: Iwao Maekawa, Isao Uchigasaki, Noboru Monma
  • Patent number: 4161471
    Abstract: Filled unsaturated ester bulk molding, sheet molding, premix or mat molding compositions are modified with elastomer to give finished products with both improved impact strength and improved surface characteristics. The elastomeric modifier is selected from the group consisting of chloroprene polymers and hydrocarbon polymers such as ethylene/propylene di-, ter-, or tetrapolymers.
    Type: Grant
    Filed: April 13, 1978
    Date of Patent: July 17, 1979
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Robert J. Kassal