Wherein Unsaturated Reactant Contains Only One Free Carboxyl Group Patents (Class 525/531)
  • Patent number: 5434225
    Abstract: An epoxy resin adhesive, sealing or coating composition containing as a curing agent an addition product of A) at least one member of the group consisting of primary amines and secondary amines and B) at least one ester having a formula selected from the group consisting of ##STR1## wherein m is 0 or 1, n is an integer from 3 to 25, 0 is an integer from 1 to 20, p is an integer from 1 to 10, R.sub.1 is selected from the group consisting of furyl, phenyl and hydrogen, R.sub.2 is hydrogen or methyl R.sub.3 is ##STR2## R.sub.5 is methylene or --CH.sub.2 --CH--CH.sub.2 --R.sub.6 --CH.sub.2 --. R.sub.6 is selected from the group consisting of ##STR3## R.sub.7 is selected from the group consisting of methylene, ##STR4## and R.sub.8 and R.sub.9 are individually ethylene or propylene.
    Type: Grant
    Filed: December 6, 1994
    Date of Patent: July 18, 1995
    Assignee: Rutgerswerke AG
    Inventors: Alfred Mathes, Ulrich Grundke, Bert Meier, Jurgen Zehrfeld
  • Patent number: 5426150
    Abstract: A storage-stable suspension of an epoxy resin hardener and a toughener useful as a molding composition is prepared via a) the addition of an organic solvent to an aqueous emulsion of the toughener when using a water-sensitive hardener, such as a polycarboxylic anhydride, removing the water as an azeotrope by vacuum distillation, then adding the epoxy resin hardener and removing the residual solvent by vacuum distillation, or b) the addition of an aqueous emulsion of the toughener with or without an organic solvent to the epoxy resin hardener when using a water-insensitive hardener such as a polyamine, and removing the water and any organic solvent by vacuum distillation.
    Type: Grant
    Filed: May 10, 1994
    Date of Patent: June 20, 1995
    Assignee: Ciba-Geigy Corporation
    Inventors: Sameer H. Eldin, Robert P. Peyer, Frans Setiabudi
  • Patent number: 5426140
    Abstract: Resurfacing surfaces of highways, roads, etc. to provide skid-resistant surface by preparing polymer concrete composition containing a curable polymer composition containing ethylenically unsaturated polymer having carbon-bonded carboxyl groups and/or hydroxyl groups and at least one reactive thickener comprising Group IIA metal oxide or hydroxide or a polyisocyanate; mixing the resulting mixture with aggregate; coating said surface with the resulting composition; compacting and shaping the resulting composition and curing the compacted, shaped composition on said surface.
    Type: Grant
    Filed: July 14, 1993
    Date of Patent: June 20, 1995
    Assignee: Frank Fekete
    Inventors: Frank Fekete, David J. Thrash
  • Patent number: 5420172
    Abstract: Cross-linked epoxy resins having nonlinear optical properties may be used in nonlinear optical media. These cross-linked epoxy resins may have the following structure: ##STR1## Z.sup.1 and Z.sup.2 being NLO-chromophores.
    Type: Grant
    Filed: August 23, 1993
    Date of Patent: May 30, 1995
    Assignee: Siemens Aktiengesellschaft
    Inventors: Jens Nordmann, Rainer Puehl
  • Patent number: 5415894
    Abstract: A method for enhancing the surface appearance of thermoset FRP wherein a thin rubbery coating is applied to a sheet molded compound (SMC). This coating, when applied to FRP inhibits propagation of micro cracks to the surface of compliant rubbery coating of the parts, while not sacrificing the physical properties of the molded parts. The coating also supplies a suitable smooth surface for automotive body panel applications that serves as a substrate for further paint applications.
    Type: Grant
    Filed: June 1, 1994
    Date of Patent: May 16, 1995
    Assignee: GenCorp Inc.
    Inventor: Frederick J. McGarry
  • Patent number: 5416173
    Abstract: An amine reacted acrylated epoxy resin blend that is particularly suitable for impregnating a fiber material and at least initial curing by exposure to ionizing radiation. These epoxy resins are basically produced by combining epoxy resins, including esterified epoxy resins, with stoichiometric quantities of aliphatic or cyclo aliphatic polyamines. The resins can be used to impregnate fibers which are exposed to ionizing radiation such as an electron beam or ultraviolet light and immediately formed into a structure, such as by filament winding. A short exposure to the ionizing radiation produces a stress-free, self supporting structure that can be fully cured through simple heating without elaborate tooling, vacuum bagging, autoclaves or the like.
    Type: Grant
    Filed: July 15, 1994
    Date of Patent: May 16, 1995
    Assignee: Martin Marietta Corporation
    Inventors: John Gagliani, Ronald K. Giesy
  • Patent number: 5395900
    Abstract: An acrylated epoxy resin based on bisphenol-S having a formula as follows ##STR1## wherein ph is phenylene or halophenylene; R.sub.1 is C.sub.2 -C.sub.4 alkylene;R.sub.2 is --CH.sub.2 CH(OH)CH.sub.2 --;R.sub.3 is acryloyl or methacryloyl;m is 0-4 integer, n is 0-4 integer and k is 0-5 integer.
    Type: Grant
    Filed: September 27, 1993
    Date of Patent: March 7, 1995
    Assignee: National Science Council
    Inventors: Der-Jan Liaw, Wen-Chang Shen
  • Patent number: 5393850
    Abstract: Vinyl ester resins of the type already having reactive liquid polymers reacted into the backbone of the resins, are cured in the presence of a reactive liquid polymer additive admixed with the prereacted vinyl ester resin. Heating of the system during cure causes the reactive liquid polymer additive to miscibilize with the vinyl ester base resin. The vinyl ester resin modified in the manner described above shows a significant enhancement in toughness as measured by fracture energy over unmodified counterparts or counterparts modified by known methods of adduction or admixing alone.
    Type: Grant
    Filed: January 6, 1993
    Date of Patent: February 28, 1995
    Assignee: The B. F. Goodrich Company
    Inventors: Alan R. Siebert, C. Dale Guiley
  • Patent number: 5391399
    Abstract: A fiber glass reinforced plastic can be in-mold coated utilizing a free radical peroxide initiated thermosetting composition of at least one polymerizable epoxy based oligomer having at least two acrylate groups, at least one copolymerizable ethylenically unsaturated monomer, at least one copolymerizable monoethylenically unsaturated compound having a --CO-- group and a --NH.sub.2, --NH-- and/or --OH group, and other conventional components such as at least one zinc salt of a fatty acid, at least one accelerator, at least one filler, and the like. The thermosetting compositions of the present invention utilize a very low or nil amount of an adhesion agent such as a polyvinyl acetate and unexpectedly achieves better flow and good coverage at reduced coating weights.
    Type: Grant
    Filed: June 9, 1994
    Date of Patent: February 21, 1995
    Assignee: GenCorp Inc.
    Inventors: David S. Cobbledick, Donald F. Reichenbach, Brian Sullivan, Robert L. Spencer
  • Patent number: 5385963
    Abstract: ABA block copolymers having saturated polyester midblocks "B" and unsaturated polyester condensation end blocks A of molecular weight from about 100 to 500 or 600 are described which increase the flexural strain to failure of unsaturated polyester or vinyl ester resins. These ABA block copolymers are generally compatible with unsaturated polyester resins and increase flexural strain by a different mechanism than used by incompatible rubbery polymers. These ABA block copolymers are compatible with the unsaturated polyester compositions and do not phase separate.
    Type: Grant
    Filed: January 7, 1993
    Date of Patent: January 31, 1995
    Assignee: GenCorp Inc.
    Inventors: Douglas S. McBain, Earl G. Melby, Kevin P. LaJudice
  • Patent number: 5371117
    Abstract: A sprayable, high solids, low-volatiles filler composition is provided which may be used as a coating on a variety of substrates. The sprayable filler composition comprises a first filler/glazing component formed from a mixture of a resin, a filler, a mixture of thixotropic clays, activated fumed silica, hollow glass microspheres, and a ketone solvent. The sprayable filler composition has a second catalyst component. The glazing/filler component is blended with the catalyst component, preferably either internally or externally of the spray nozzle, and the resultant sprayable filler composition is sprayed onto a substrate. The resulting cured coating provides a sandable surface which is corrosion resistant.
    Type: Grant
    Filed: November 30, 1993
    Date of Patent: December 6, 1994
    Assignee: Fibre Glass-Evercoat Company, Inc.
    Inventors: David M. Parish, Kenneth E. Lewis
  • Patent number: 5362799
    Abstract: An unsaturated polyester resin composition is described that contains an amine-terminated flexible polymer that can react with the unsaturation in the polyester. A compatible system results that has higher fracture toughness. The preferred amine-terminated flexible polymer is an amine-terminated poly(butadiene-co-acrylonitrile). The resin composition can be extended with fillers and reinforced with fibers. In these applications, the resin is known as a matrix resin.
    Type: Grant
    Filed: September 13, 1993
    Date of Patent: November 8, 1994
    Assignee: GenCorp Inc.
    Inventors: Frederick J. McGarry, Ramnath Subramaniam
  • Patent number: 5362819
    Abstract: A block copolymer of generally an AB, ABA, or A(BA).sub.n structure, or mixtures thereof where the A block is an unsaturated polyester, the B block is a flexible polymer having a Tg of 0.degree. C. or lower, and n is 2 to 5. The various block components are generally first separately prepared as polymers with the flexible polymer generally having 1 or 2 functional end groups such as an amine group, a carboxyl group, or a hydroxyl group with the later being preferred. Alternatively, for low molecular weight unsaturated polyester blocks, the block can be made in situ. The preferred reaction route is to react a mono or dihydroxy terminated flexible polymer with a diisocyanate which subsequently can be readily reacted with the polyester. The block copolymers can be utilized as toughening agents.
    Type: Grant
    Filed: January 30, 1992
    Date of Patent: November 8, 1994
    Assignee: GenCorp Inc.
    Inventors: Douglas S. McBain, Andrew L. Ratermann, I. Glen Hargis, Earl G. Melby, Kevin P. LaJudice
  • Patent number: 5359002
    Abstract: A fiber glass reinforced plastic can be in-mold coated utilizing a free radical peroxide initiated thermosetting composition of at least one polymerizable epoxy based oligomer having at least two acrylate groups, at least one copolymerizable ethylenically unsaturated monomer, at least one copolymerizable monoethylenically unsaturated compound having a --CO-- group and a --NH.sub.2, --NH-- and/or --OH group, and other conventional components such as at least one zinc salt of a fatty acid, at least one accelerator, at least one filler, and the like. The thermosetting compositions of the present invention utilize a very low or nil amount of an adhesion agent such as a polyvinyl acetate and unexpectedly achieves better flow and good coverage at reduced coating weights.
    Type: Grant
    Filed: September 13, 1993
    Date of Patent: October 25, 1994
    Assignee: GenCorp Inc.
    Inventors: David S. Cobbledick, Donald F. Reichenbach, Brian Sullivan, Robert L. Spencer
  • Patent number: 5350814
    Abstract: A unsaturated polyester resin composition is described that contains an epoxy resin reacted with an amine-terminated flexible polymer while dissolved in the unsaturated polyester resin and its ethylenically unsaturated crosslinking monomer. A compatible system results from the reaction which has a controllable modulus based on the amount of flexible polymer included in the resin. The resin is generally transparent if unfilled and has a higher calculated fracture energy than similar unsaturated polyester resin without modification. The unsaturated polyester resin can be filled with particulate filler or reinforced with fibrous fillers.
    Type: Grant
    Filed: August 6, 1993
    Date of Patent: September 27, 1994
    Assignee: GenCorp Inc.
    Inventors: Frederick J. McGarry, Ramnath Subramaniam
  • Patent number: 5344897
    Abstract: Liquid coating agent based on a polymer containing acetoacetate groups and a polyamine in the form of the corresponding aldimine or ketimine, the polymer containing acetoacetate groups being obtained by reaction of a polyepoxide with water, an amine or a hydroxycarboxylic acid and subsequent esterification or transesterification with acetoacetic acid. These liquid coating agents are particularly suitable as binders in two-component automobile repair fillers or as two-component primers.
    Type: Grant
    Filed: October 29, 1993
    Date of Patent: September 6, 1994
    Assignee: Hoechst AG
    Inventors: Gerhard Brindoepke, Uwe Kubillus, Helmut Plum
  • Patent number: 5336735
    Abstract: A flame-retardant thermoplastic resin composition is disclosed, comprising (A) a thermoplastic resin and (B-1) a halogenated epoxy resin whose epoxy groups are blocked by a long chain aliphatic carboxylic acid or (B-2) a mixture prepared by melt mixing (b1) a halogenated epoxy resin or (b2) a halogenated epoxy resin whose epoxy groups are blocked with (b3) a long chain aliphatic carboxylic acid. The composition has easy release from mold and satisfactory thermal stability during molding.
    Type: Grant
    Filed: September 14, 1992
    Date of Patent: August 9, 1994
    Assignee: Dainippon Ink and Chemicals, Inc.
    Inventors: Katsuji Takahashi, Yuji Sath, Takehisa Mizuno
  • Patent number: 5332785
    Abstract: A liquid coating composition based on a polymer containing acetoacetate groups and a polyamine in the form of the corresponding aldimine or ketimine, the polymer containing acetoacetate groups being obtained by reacting a polyepoxide containing hydroxyl groups, or a polyepoxide which is partially or completely reacted with monocarboxylic acids, with acetoacetic acid derivatives. These liquid coating compositions are suitable in particular as binders in two-component fillers for automotive refinishing or as two-component primers.
    Type: Grant
    Filed: March 29, 1993
    Date of Patent: July 26, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Gerhard Brindoepke
  • Patent number: 5332781
    Abstract: Storage-stable suspension comprised of a solid or liquid epoxy resin hardener and a solid or liquid toughener suspended therein is distinguished by excellent homogeneous dispersion of the toughener in the epoxy resin hardener and are suitable for preparing suspensions of curable epoxy resin compositions.
    Type: Grant
    Filed: June 22, 1993
    Date of Patent: July 26, 1994
    Assignee: Ciba-Geigy Corporation
    Inventors: Sameer H. Eldin, Robert P. Peyer, Frans Setiabudi
  • Patent number: 5331080
    Abstract: Acid functional compounds which are the reaction products of monoepoxides, phosphorus-containing acids and cyclic anhydrides are disclosed. The reaction products promote adhesion and prevent yellowing when added to curable film-forming compositions.
    Type: Grant
    Filed: September 2, 1993
    Date of Patent: July 19, 1994
    Assignee: PPG Industries, Inc.
    Inventors: Shanti Swarup, Gregory J. McCollum, Paul J. Prucnal, Debra L. Singer
  • Patent number: 5326795
    Abstract: Storage stable thermosettable ethylenically unsaturated resins containing at least one 1,4-naphthoquinone substituted on the 2 or 3 or both the 2 and 3 positions. The reactivity of these storage stable resins with curing agents is not unacceptably reduced by the presence of the stabilizer. The compositions are useful in the preparation of laminates or composites and in filament winding pultrusion, braiding and resin transfer molding applications.
    Type: Grant
    Filed: October 20, 1993
    Date of Patent: July 5, 1994
    Assignee: The Dow Chemical Company
    Inventor: Paul L. Wykowski
  • Patent number: 5319060
    Abstract: A method of preparing an unsaturated ester resin having improved storage stability is disclosed. An epoxy compound and polymerizable unsaturated monocarboxylic acid are reacted in the presence of a trivalent organic phosphorous catalyst. The catalyst is subsequently deactivated by oxidation. The resin may then be reacted with an acid anhydride.
    Type: Grant
    Filed: June 22, 1993
    Date of Patent: June 7, 1994
    Assignee: W. R. Grace & Co.-Conn.
    Inventors: Katsue Nishikawa, Yoshichi Hagiwara
  • Patent number: 5318719
    Abstract: This invention relates to a novel class of biodegradable water-soluble graft copolymers having building, anti-filming, dispersing and threshold crystal inhibiting properties comprising (a) an acid functional monomer and optionally (b) other water-soluble, monoethylenically unsaturated monomers copolymerizable with (a) grafted to a biodegradable substrate comprising polyalkylene oxides and/or polyalkoxylated materials.
    Type: Grant
    Filed: November 12, 1991
    Date of Patent: June 7, 1994
    Assignee: Rohm and Haas Company
    Inventors: Kathleen A. Hughes, Graham Swift
  • Patent number: 5310826
    Abstract: Accelerator compositions for the free radical polymerization of unsaturated polyesters and for the curing of unsaturated polyesters and polyurethanes are disclosed. More particularly, use is made of complexes of thiolic compounds with metal salts as the accelerators. In more preferred embodiments, the accelerators also include oxygen-containing compounds or phosphorus-containing compounds. Also disclosed are curable resin compositions comprising these accelerators and polymerization and curing processes employing these accelerators.
    Type: Grant
    Filed: October 21, 1991
    Date of Patent: May 10, 1994
    Assignees: Akzo N.V., Saint Peter S.r.l.
    Inventor: Gualtiero Giovando
  • Patent number: 5302669
    Abstract: A curable resin comprising units of at least one prepolymer selected from the group consisting of a prepolymer (C) and a prepolymer (F); the prepolymer (C) having the formula (I): ##STR1## and the prepolymer (F) having the formula (III): ##STR2## The curable resin has the excellent flexibility, solvent resistance and adhesion to organic materials and the properties thereof can be controlled accordingly to desire, in addition to the excellent curability at ordinary temperature, adhesion to inorganic materials and weatherability.
    Type: Grant
    Filed: September 21, 1992
    Date of Patent: April 12, 1994
    Assignee: Kanegafuchi Kagaku Kogyo Kabushiki Kaisha
    Inventors: Hisao Furukawa, Naotami Ando, Yasushi Kato
  • Patent number: 5298543
    Abstract: Curable compositions from storage stable thermosettable ethylenically unsaturated resins containing at least one 1,4-naphthoquinone substituted on the 2 or 3 or both the 2 and 3 positions. The reactivity of these storage stable resins with curing agents is not unacceptably reduced by the presence of the stabilizer. The curable compositions are useful in the preparation of laminates or composites and in filament winding pultrusion, braiding and resin transfer molding applications.
    Type: Grant
    Filed: July 28, 1993
    Date of Patent: March 29, 1994
    Assignee: The Dow Chemical Company
    Inventor: Paul L. Wykowski
  • Patent number: 5292833
    Abstract: The invention relates to a thermosetting reactive resin mixture ofa) at least one organic compound, which possesses at least two epoxide groups,b) at least one carbamate compound of the formulae I, II, III or IV, such as can be quoted from the claim petitions,c) at least one basic catalyst,and with or withoutd) other processing aids and/or additives.The thermosetting reactive resin mixture according to the present invention are used for chemically resistant coatings, as cross-linked, no longer soluble and infusible moulded articles, for the production of cathodically precipitable electrophoretic enamels, and for the production of coating powders and automobile paints.
    Type: Grant
    Filed: December 30, 1991
    Date of Patent: March 8, 1994
    Assignee: Dainippon Ink and Chemicals, Inc.
    Inventors: Gerwald F. Grahe, Arthur Lachowicz, Roland Fromme
  • Patent number: 5288360
    Abstract: An adhesive resin composition comprising a polymer of a radically polymerizable epoxy resin (I) and a monomer (c), the radically polymerizable epoxy resin (I) being a reaction product between an epoxy resin (a) and a radically polymerizable monomer (b) having a function group reactive to epoxy group or hydroxyl group in said epoxy resin (a), having an equivalent ratio (b)/(a)=0.01.about.0.9 and said monomer (c) being copolymerizable with said radically polymerizable epoxy resin (I) and containing alkyl (meth)acrylate and/or a fluorine-containing unsaturated monomer serving as an indispensable component. The adhesive resin composition has an excellent adhesion between fluorine-contained resins and metal substrates.
    Type: Grant
    Filed: October 9, 1992
    Date of Patent: February 22, 1994
    Assignee: Mitsubishi Petrochemical Company, Ltd.
    Inventors: Kazuhide Hayama, Kazuyuki Hata, Keizo Abe, Takahiro Ozu
  • Patent number: 5288802
    Abstract: Curable coating compositions are provided containing an amine group containing polyepoxide resin, an acetoacetate containing polyester having a weight average molecular weight of at least 1000, and a polyacrylate containing material. The amine group containing polyepoxide can be modified with a ketone and/or an aldehyde to form a ketimine and/or an aldimine containing polyepoxide. The compositions are useful as coatings, particularly as ambient or low temperature curable automotive refinish primer coatings having good corrosion resistance, adhesion to both substrate and other organic coatings, sandability and pot-life.
    Type: Grant
    Filed: January 25, 1993
    Date of Patent: February 22, 1994
    Assignee: PPG Industries, Inc.
    Inventors: David N. Walters, Cathy A. Kreutzer, Padmanabhan Sundararaman
  • Patent number: 5283299
    Abstract: Aqueous-based crosslinkable coating composition comprising an aqueous dispersion of at least one polymer having epoxy-reactive functional groups, at least one polyepoxide compound, and at least one metal chelate complex epoxy-cure catalyst.
    Type: Grant
    Filed: May 7, 1992
    Date of Patent: February 1, 1994
    Assignee: ICI Americas, Inc.
    Inventors: Valentino J. Tramontano, Milton Lapkin, Scott D. Rothenberger
  • Patent number: 5281678
    Abstract: A method of preparing an unsaturated ester resin having improved storage stability is disclosed. An epoxy compound and polymerizable unsaturated monocarboxylic acid are reacted in the presence of a trivalent organic phosphorous catalyst. The catalyst is subsequently deactivated by oxidation. The resin may then be reacted with an acid anhydride.
    Type: Grant
    Filed: November 19, 1991
    Date of Patent: January 25, 1994
    Assignee: W. R. Grace & Co.
    Inventors: Katsue Nishikawa, Yoshichi Hagiwara
  • Patent number: 5276097
    Abstract: The present invention relates to coating agents containingA) one or more polymers containing carboxyl groups and having a number-average molecular weight of 500 to 8,000 and an acid number of 15 to 200 mg of KOH/g as the essential binder component andB) one or more compounds containing epoxide groups as crosslinking agents,wherein the compound B containing epoxide groups is a copolymer containing epoxide groups, has a number-average molecular weight M.sub.n of 300 to 5,000, preferably 500 to 3,500, and a heterogeneity (M.sub.w /M.sub.n), measured by gel permeation chromatography, of .ltoreq.3, preferably of .ltoreq.2, and has been prepared by continuous bulk polymerization at temperatures between 130.degree. and 350.degree. C. and pressures above 1 bar.The invention also relates to processes for the preparation of the coating agent and the use of the coating agents in automobile refinishing.
    Type: Grant
    Filed: January 24, 1992
    Date of Patent: January 4, 1994
    Assignees: BASF Lacke, Farben Aktiengesellschaft
    Inventors: Peter Hoffmann, Werner Alfons Jung, Elisabeth Kappes, Manfred Niessner
  • Patent number: 5274028
    Abstract: In an improved method for producing a surface graft of a hydrophilic polymer upon a preformed solid or semi-solid polymer substrate having hydroperoxide groups along its surface, n-vinyl pyrrolidone is utilized as the surface-grafting monomer, the substrate is selected to be insoluble in n-vinyl pyrrolidone, and the polymerization is carried out in aqueous alkaline conditions utilizing a combination of metal salts to provide a variable valence metal ion in a reduced state capable of oxidizing to suppress homopolymerization of the monomer in the solution.When the substrate is at least partially soluble in the n-vinyl pyrrolidone, an ethylenically unsaturated monomer having a higher reactivity with the substrate than n-vinyl pyrrolidone is added to the alkaline polymerization solution as a "seeding" monomer. Addition of the "seeding" monomer results in a surface-grafted copolymer effectively externalized from the substrate.
    Type: Grant
    Filed: December 6, 1990
    Date of Patent: December 28, 1993
    Assignee: Baxter International Inc.
    Inventors: William J. Bertrand, Stephen L. Coulter, Cary Reich, Paul DeAntonio
  • Patent number: 5272197
    Abstract: Thermosettable ethylenically unsaturated resins are rendered storage stable by the addition of at least one 1,4-naphthoquinone substituted on the 2 or 3 or both the 2 and 3 positions. The reactivity of these storage stable resins with curing agents is not unacceptably reduced by the presence of the stabilizer.
    Type: Grant
    Filed: April 1, 1992
    Date of Patent: December 21, 1993
    Assignee: The Dow Chemical Company
    Inventor: Paul L. Wykowski
  • Patent number: 5268435
    Abstract: A polyol resin substantially free of epoxy groups is useful as a coating material and is prepared by(i) reacting a bisphenol epoxy resin with a compound having one active hydrogen per molecule and optionally a bisphenol to form a polyol resin having secondary hydroxyl groups, and(ii) esterifying part of the secondary hydroxyl groups with a lactone or a monocarboxylic acid (ester) to form a polyol resin with graft-polymerized polyester moieties.
    Type: Grant
    Filed: June 12, 1991
    Date of Patent: December 7, 1993
    Assignees: Mitsui Petrochemical Industries, Ltd., Ricoh Company, Ltd.
    Inventors: Hideo Nakamura, Masaru Wakizaka, Yohzoh Yamamoto
  • Patent number: 5264503
    Abstract: An elastomer-modified phenolic composition is provided which is an reaction product of a phenolic compound and about 5 to about 35 weight percent, based on the total weight of the elastomer-modified phenolic compound, of a functionalized elastomer. Further, there is provided a composition comprising an epoxy resin and a curing agent for the epoxy resin comprising the elastomer-modified phenolic composition. The use of the elastomer-modified phenolic curing agent permits the preparation of low-viscosity powder coating formulations for impact-resistant coatings.
    Type: Grant
    Filed: January 29, 1990
    Date of Patent: November 23, 1993
    Assignee: Shell Oil Company
    Inventor: Edward J. Marx
  • Patent number: 5262456
    Abstract: A halogen free casting resin suitable for covering electron devices with a fire retardant material contains an acidic ester of an hydroxy-functional phosphor compound and an organic anhydride. A stable mixture can be generated from the acidic ester and the hardener component of the casting resin, and further used for the hardening of epoxides resins. The acidic ester is chemically integrated in the epoxide resin matrix in a stable mixture, thereby improving the long term fire-retardancy of the casting resin molding compound without increasing the volatility of the mixture.
    Type: Grant
    Filed: November 5, 1992
    Date of Patent: November 16, 1993
    Assignee: Siemens Aktiengesellschaft
    Inventors: Ernst Wipfelder, Winfried Plundrich
  • Patent number: 5248742
    Abstract: A unsaturated polyester resin composition is described that contains an epoxy resin reacted with an amine-terminated flexible polymer while dissolved in the unsaturated polyester resin and its ethylenically unsaturated crosslinking monomer. A compatible system results from the reaction which has a controllable modulus based on the amount of flexible polymer included in the resin. The resin is generally transparent if unfilled and has a higher calculated fracture energy than similar unsaturated polyester resin without modification. The unsaturated polyester resin can be filled with particulate filler or reinforced with fibrous fillers.
    Type: Grant
    Filed: April 27, 1992
    Date of Patent: September 28, 1993
    Assignee: GenCorp Inc.
    Inventors: Frederick J. McGarry, Ramnath Subramaniam
  • Patent number: 5242708
    Abstract: Resurfacing surfaces of highways, roads, etc. to provide skid-resistant surface by preparing polymer concrete composition containing a curable polymer composition containing ethylenically unsaturated polymer having carbon-bonded carboxyl groups and/or hydroxyl groups and at least one reactive thickener comprising Group IIA metal oxide or hydroxide or a polyisocyanate; mixing the resulting mixture with aggregate; coating said surface with the resulting composition; compacting and shaping the resulting composition and curing the compacted, shaped composition on said surface.
    Type: Grant
    Filed: May 11, 1992
    Date of Patent: September 7, 1993
    Assignee: Frank Fekete
    Inventors: Frank Fekete, David T. Thrash
  • Patent number: 5218063
    Abstract: An epoxy composition suitable for adhesives, coatings and sealants is prepared from (a) at least one reaction product of an epoxy and amine-capped oligomer, (b) an epoxy adduct of dimer acid, (c) dicyandiamide and (d) a catalyst which yields a dimethyl amine radical upon being heated. When the epoxy composition is cured, it exhibits two glass transition temperatures and good adhesion properties at and below room temperature. The epoxy is particularly suitable for adhesives used in the manufacturing of automobiles.
    Type: Grant
    Filed: June 26, 1991
    Date of Patent: June 8, 1993
    Assignee: W. R. Grace & Co.-Conn.
    Inventor: Michael E. Kimball, deceased
  • Patent number: 5212241
    Abstract: A protective paint coating containing a polymeric binder having both hydrophobic and hydrophilic moieties in the polymeric structure comprises an acrylic-graft terpolymer. The terpolymer comprises aliphatic-modified glycidyl acrylate and epoxy resin coreacted with diphenol to form the terpolymer. Ethylenically unsaturated monomers, including carboxyl monomers, are in-situ copolymerized in the presence of the terpolymer to produce the acrylic-graft terpolymer. The aliphatic-modified glycidyl acrylate component of the terpolymer comprise the reaction product of a glycidyl acrylate and an aliphatic ethylenic monomer having a chain of 2 to 20 carbon atoms. The aliphatic chain and the carboxyl functionality provide the self-contained wetting agent properties to the polymeric binder structure.
    Type: Grant
    Filed: May 15, 1992
    Date of Patent: May 18, 1993
    Assignee: The Glidden Company
    Inventors: James T. K. Woo, Gary C. Pompignano, Kevan A. Packard
  • Patent number: 5204378
    Abstract: The fluorine-containing epoxy(meth)acrylate resin of the invention is represented by the following general formula (I). ##STR1## wherein R.sub.f is selected from the group consisting of --.phi.--C(CF.sub.3).sub.2 --.phi.--(where .phi. stands for ##STR2## --C(CF.sub.3).sub.2 --.phi.'--C(CF.sub.3).sub.2 --(where .phi.' stands for and --CH.sub.2 (CF.sub.2).sub.6 CH.sub.2 --; n is zero or a positive interger; and X is hydrogen or methyl group. The resin of the invention may be prepared by reacting a diglycidyl ether of a fluorine-containing hydrocarbon (R.sub.f) with acrylic acid or methacrylic acid. Further provided is an adhesive composition comprising the aforementioned fluorine-containing epoxy(meth)acrylate resin and a photo-polymerization initiator, which can be cured at room temperature within a short time by irradiation with UV rays to form a cured product having a refractive index N.sub.D.sup.20 ranging from 1.434 to 1.532.
    Type: Grant
    Filed: March 18, 1991
    Date of Patent: April 20, 1993
    Assignee: Nippon Telegraph and Telephone Corporation
    Inventors: Tohru Maruno, Shigeki Ishibashi, Kouzaburou Nakamura
  • Patent number: 5204386
    Abstract: A thixoropic adhesive composition exhibiing good sag resistance is prepared comprising a mixture of a polymer-modified epoxy resin and a rheological control agent. The polymer-modified epoxy resin is preferably a dispersion of acrylic elastomer in an epoxy resin in which the acrylic elastomer particles have added hydroxyl functionality which interacts favorably with rheological control agents, such as fumed silica. Acrylic epoxy resin dispersions containing added hydroxyl functionality give improved rheological control.
    Type: Grant
    Filed: June 9, 1992
    Date of Patent: April 20, 1993
    Assignee: The Dow Chemical Company
    Inventors: Yasemin Ersun-Hallsby, Dwight K. Hoffman, Gerald C. Kolb, Gene D. Rose
  • Patent number: 5198510
    Abstract: Vinyl ester resins of the type already having reactive liquid polymers reacted into the backbone of the resins, are cured in the presence of a reactive liquid polymer additive admixed with the prereacted vinyl ester resin. Heating of the system during cure causes the reactive liquid polymer additive to miscibilize with the vinyl ester base resin. The vinyl ester resin modified in the manner described above shows a significant enhancement in toughness as measured by fracture energy over unmodified counterparts or counterparts modified by known methods of adduction or admixing alone.
    Type: Grant
    Filed: January 22, 1991
    Date of Patent: March 30, 1993
    Assignee: The B. F. Goodrich Company
    Inventors: Alan R. Siebert, C. Dale Guiley
  • Patent number: 5196296
    Abstract: Epoxy acrylate resins of this invention having a structure of the general formula (I) ##STR1## in which R is hydrogen or a lower alkyl group, R' is hydrogen or methyl group, and n is an integer from 0 to 20 are heat-resistant, solvent-soluble, and photosensitive and photosensitive resin compositions containing said epoxy acrylate resins as main component exhibit high photosensitivity in addition to strong adhesion to substrates, good resistance to heat and chemicals, and good mechanical and electrical properties and are useful as materials for forming insulation films for multilayer devices and protective films for image sensors and as protective films for solder resists, plating resists, and color filters.
    Type: Grant
    Filed: July 26, 1990
    Date of Patent: March 23, 1993
    Assignees: Nippon Steel Corporation, Nippon Steel Chemical Co., Ltd.
    Inventors: Kazuhiro Watanabe, Takero Teramoto
  • Patent number: 5191039
    Abstract: The fluorine-containing epoxy(meth)acrylate resin of the invention is represented by the following general formula (I). ##STR1## wherein R.sub.f is selected from the group consisting of --.phi.--C(CF.sub.3).sub.2 --.phi.-- (where .phi. stands for ##STR2## --C(CF.sub.3).sub.2 --.phi.'--C(CF.sub.3).sub.2 -- (where .phi.' stands for ##STR3## and --CH.sub.2 (CF.sub.2).sub.6 CH.sub.2 --; n is zero or a positive integer; and X is hydrogen or methyl group. The resin of the invention may be prepared by reacting a diglycidyl ether of a fluorine-containing hydrocarbon (R.sub.f) with acrylic acid or methacrylic acid. Further provided is an adhesive composition comprising the aforementioned fluorine-containing epoxy(meth)acrylate resin and a photo polymerization initiator, which can be cured at room temperature within a short time by irradiation with an UV ray to form a cured product having a refractive index n.sub.D.sup.20 ranging from 1.434 to 1.532.
    Type: Grant
    Filed: May 2, 1991
    Date of Patent: March 2, 1993
    Assignee: Nippon Telegraph and Telephone Corporation
    Inventors: Tohru Maruno, Shigeki Ishibashi, Kouzaburou Nakamura
  • Patent number: 5189102
    Abstract: A method for producing a vinyl resin comprising the steps of dissolving or dispersing a polymerizable vinyl monomer in a polymerization solvent containing a silicone oil, and polymerizing the polymerizable vinyl monomer in the presence of a polymerization catalyst.
    Type: Grant
    Filed: March 4, 1992
    Date of Patent: February 23, 1993
    Assignee: Ricoh Company, Ltd.
    Inventors: Kazuo Tsubuko, Shinichi Kuramoto, Kazuhiko Umemura, Hidemi Uematsu, Okawara, Makoto
  • Patent number: 5175219
    Abstract: The invention relates to new compounds of the general formula ##STR1## where R is a divalent, optionally branched aliphatic, cyclic or alicyclic hydrocarbon group having from 2 to 10 carbon atoms; R.sup.1 and R.sup.2 are, independently of one another, hydrogen, or aliphatic or aromatic hydrocarbon groups; R.sup.3 is --COOH, --CN, --COOC.sub.2 H.sub.4 --OH, --CONH--NH.sub.2 or --COOR.sup.4 ; R.sup.4 is an aliphatic hydrocarbon group having from 1 to 4 carbon atoms; and n is 2 or 3.
    Type: Grant
    Filed: March 28, 1991
    Date of Patent: December 29, 1992
    Assignee: Schering AG
    Inventors: Christian Burba, Werner Mrotzek
  • Patent number: 5175207
    Abstract: A diallyl aromatic dicarboxylate derivative of the formula ##STR1## wherein Y is hydrogen atom or perfluoroalkenyl group having 6 to 14 carbon atoms, is a novel compound. The compound (1) is a starting material for a prepolymer containing a repeating unit derived from diallyl aromatic fluorine-containing dicarboxylate and represented by the formula ##STR2## wherein X is perfluoroalkenyl group having 6 to 14 carbon atoms.
    Type: Grant
    Filed: October 31, 1990
    Date of Patent: December 29, 1992
    Assignee: Daikin Industries Ltd.
    Inventors: Sinji Tamaru, Motonobu Kubo
  • Patent number: 5175220
    Abstract: The invention relates to new compounds of the general formulas ##STR1## where R is a divalent, optionally branched aliphatic, cyclic or alicyclic hydrocarbon group having from 2 to 10 carbon atoms; R.sup.1 and R.sup.2 are, independently of one another, hydrogen, or aliphatic or aromatic hydrocarbon groups; R.sup.3 is --COOH, --CN, --COOC.sub.2 H.sub.4 --OH, --CONH--NH.sub.2 or --COOR.sup.4 ; R.sup.4 is an aliphatic hydrocarbon group having from 1 to 4 carbon atoms; and n is 2 or 3.
    Type: Grant
    Filed: January 3, 1992
    Date of Patent: December 29, 1992
    Assignee: Schering AG
    Inventors: Christian Burba, Werner Mrotzek