Contacting Polymer From Ethylenic Reactants Only With Ethylenic Reactant Wherein Said Contacting Is Either Concurrent With Or Subsequent To The Contacting With The Saturated Poly 1,2-epoxy Reactant Patents (Class 525/112)
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Patent number: 5124406Abstract: The present invention relates to an epoxy ester coating copolymer resin which is useful in the preparation of an air curable, high solids coating, which resin is the reaction product of components (I), (II) and (III); wherein (I) is a polymerizable base of (a) a fatty acid having free radical polymerizable double bonds and (b) a vinyl monomer selected from the group consisting of styrenes, vinyl toluene and mixtures thereof; (II) is an epoxy resin and (III) is a monobasic acid. The epoxy ester copolymer resin of the invention is prepared by the reaction of (I), (II) and (III) at an elevated temperature to an acid number below 10.Type: GrantFiled: December 28, 1990Date of Patent: June 23, 1992Assignee: Cargill, IncorporatedInventors: Thomas E. Rolando, Roger A. Schmidt, K. A. Pai Panandiker
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Patent number: 5098950Abstract: Disclosed is a thermosetting resin composition which includes(a) an unsaturated polyester,(b) a polymer having a (meth)acrylate group only at one or both terminals of its main chain,(c) a poly(meth)acrylate oligomer,(d) a styrene monomer, and(e) a methyl methacrylate monomer.Also, a method of molding the resin is disclosed, which includes dividing the thermosetting resin composition into two parts, adding a curing agent to one of the two parts and a curing accelerator to another to form two partial compositions, introducing the two partial compositions into a mold, and allowing the two partial compositions to mix with each other and cure.Type: GrantFiled: February 15, 1990Date of Patent: March 24, 1992Inventors: Katsuo Kagaya, Tadao Saito, Shichinosuke Ito
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Patent number: 5091498Abstract: The present invention describes the use of 1,3-dialkylimidazole-2-thiones as a catalyst for epoxy/anhydride reactions (and other reactions) and a method of making these catalysts. Epoxy/anhydride coatings containing these improved catalysts offer the following advantages: improved appearance (especially since even weeks after application the coatings still have a "wet" look); better pot-life; improved resistance to alkaline substances which will improve durability; improved solubility; and coatings which have a reduced volatile organic content (VOC).Type: GrantFiled: February 19, 1991Date of Patent: February 25, 1992Assignee: E. I. Du Pont de Nemours and CompanyInventors: Anthony J. Arduengo, III, Robert J. Barsotti, Patrick H. Corcoran
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Patent number: 5043366Abstract: A self-curing aqueous resin dispersion obtained by neutralizing a resin having at least one alicyclic epoxy group and at least two carboxyl groups in the molecule, with a base and dispersing the neutralized resin in water.Type: GrantFiled: February 16, 1990Date of Patent: August 27, 1991Assignee: Kansai Paint Co., Ltd.Inventor: Osamu Isozaki
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Patent number: 5043363Abstract: An active energy ray-curing resin composition comprises (i) a heat-crosslinkable linear copolymer comprising 5 to 30 mol % of a monomer represented by the general formula I shown below and 5 to 50 mol % of a monomer represented by the general formula II shown below as the copolymer constituents: ##STR1## (wherein R.sup.1 is hydrogen or alkyl or hydroxyalkyl group having 1 to 3 carbon atoms; R.sup.2 is hydrogen or alkyl or acyl group having 1 to 4 carbon atoms which may have a hydroxyl group; R.sup.3 is hydrogen or alkyl group having 1 to 3 carbon atoms; R.sup.4 is a divalent hydrocarbon group which may have internally an ether bond and may also be substituted with halogen atoms; and R.sup.5 is alkyl having 3 to 12 carbon atoms or phenylalkyl group or phenyl group), and (ii) a monomer having an ethylenically unsaturated bond.Type: GrantFiled: September 12, 1990Date of Patent: August 27, 1991Assignee: Canon Kabushiki KaishaInventors: Hiromichi Noguchi, Tadayoshi Inamoto, Megumi Munakata
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Patent number: 5019608Abstract: An epoxy adhesive composition for the bonding of SMC to metal substrates and other SMC parts having an improved cure rate and hence rate of initial lap shear strength development has been discovered. The adhesive composition comprises an epoxy resin and a polyacrylate or polymethacrylate cured with a combination of an amine-functional butadiene-acrylonitrile rubber and at least one polyamidoamine.Type: GrantFiled: February 7, 1989Date of Patent: May 28, 1991Assignee: Lord CorporationInventor: Dilipkumar N. Shah
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Patent number: 4980416Abstract: A heat-resistant resin composition, comprising (A) 30 to 95% by weight of at least oen unsaturated ester compound selected from the group consisting of (I) unsaturated ester compounds represented by the formula I: ##STR1## wherein R.sup.1 s independently stand for one member selected from the class consisting of ##STR2## wherein R.sup.3 and R.sup.4 independently stand for a hydrogen atom or a methyl group, and a hydrogen atom, and at least one R.sup.1 stands for ##STR3## wherein R.sup.3 and R.sup.4 independently stand for a hydrogen atom or a methyl group, and R.sup.2 s independently stand for an atom or an organic group selected from the class consisting of a hydrogen atom, halogen atoms, a methoxy group, and alkyl groups of 1 to 5 carbon atoms, and m stands for 0 or an integer in the range of 1 to 10, and (II) unsaturated ester compounds represented by the formula II; ##STR4## wherein R.sup.5 s independently stand for one member selected from the class consisting of ##STR5## wherein R.sup.3 and R.sup.Type: GrantFiled: January 3, 1989Date of Patent: December 25, 1990Assignee: Nippon Shokubai Kagaku Kogyo Co., Ltd.Inventors: Toshio Awaji, Takao Omi, Kenichi Ueda
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Patent number: 4921912Abstract: An epoxy resin composition useful as an adhesive comprises (a) 100 parts by weight of an epoxy resin or a mixture of epoxy resins, (b) from 1-20 parts by weight of an acrylic oligomer, (c) from 5-150 parts by weight of an amine, and (d) from 10-200 parts by weight of a nitrile rubber having a terminal amine group.Type: GrantFiled: August 1, 1988Date of Patent: May 1, 1990Assignee: Ciba-Geigy CorporationInventors: Hirotoshi Sagawa, Seiji Yamaguchi
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Patent number: 4921890Abstract: A process for improving the flame retardancy, hygroscopic, soil release and other properties of a polymer substrate is provided in which the substrate is contacted with a suitable aqueous mixture containing a water-soluble monomer and an organic halogen-containing hydrophobic carrier compound at a temperature of between about 40.degree. C. to 100.degree. C. Polymerization of the monomer is thereafter initiated by a chemical or physical initiator to form a polymer evenly disposed on the substrate. The flame retardancy, hygroscopic, soil release and other surface properties of the substrate are thereby improved. The mixture may be in the form of an emulsion wherein the hydrophobic carrier compound is emulsified by an appropriate agent. The invention also pertains to the improved substrates prepared in accordance with the present process.Type: GrantFiled: April 24, 1987Date of Patent: May 1, 1990Assignee: Intera Company, Ltd.Inventors: Katsumi Hayashi, Gregory A. Lentz
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Patent number: 4866134Abstract: An electric metal foil-plated laminate sheet which is obtained by laminating a cured layer of a thermosetting resin composition with electroconductive foils, said thermosetting resin composition comprising 30-85% by weight of (A) a rubber-modified vinyl ester obtained by reacting,(a) an epoxy resin,(b) a carboxyl group containing rubbery polymer derived from a conjugated diene, and(c) at least one unsaturated monocarboxylic acid selected from the group consisting of acrylic acid and methacrylic acid to react one another in amounts such that, based on 100 parts by weight of (a) the epoxy resin, (b) the carboxyl group containing rubbery polymer accounts for a proportion in the range of 5 to 80 parts by weight and that the total number of carboxylic group contained in (b) the rubbery polymer and (c) the unsaturated monocarboxylic acid falls in the range of 1.3 to 1.5 per each of the epoxy groups contained in (a) the epoxy resin at a temperature of 90.degree. to 120.degree. C.Type: GrantFiled: April 21, 1988Date of Patent: September 12, 1989Assignees: Matsushita Electric Works, Ltd., Nippon Shokubai Kagaku Kogyo Co., Ltd.Inventors: Hidekazu Takano, Tetsuo Kunitomi, Shigehiro Okada, Toshio Awaji, Katsuaki Shindo, Daisuke Atobe
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Patent number: 4857131Abstract: A two-part, heat stable, peroxide-free adhesive that can be mixed in equal parts with rapid cure for the bonding of plastics and metals has been discussed. Part A of the adhesive contains a polymeric material, an olefinically unsaturated monomer, an acid material, a compound containing a sulfonyl halide group, and a compound containing a transition metal; and Part B contains a polymeric material (preferably a phenoxy resin) and monomer of the same class and a Zn, Cu or Cd metal powder.Type: GrantFiled: November 27, 1987Date of Patent: August 15, 1989Assignee: Lord CorporationInventors: Dennis J. Damico, Kenneth W. Mushrush, Ruth M. Bennett
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Patent number: 4803232Abstract: An epoxy adhesive composition for the bonding of SMC to metal substrates and other SMC parts having an improved cure rate and hence rate of initial lap shear strength development has been discovered. The adhesive composition comprises an epoxy resin and a polyacrylate or polymethacrylate cured with a combination of an amine-functional butadiene-acrylonitrile rubber, at least one aliphatic or aromatic polyamine and at least one polyamide.Type: GrantFiled: July 30, 1987Date of Patent: February 7, 1989Assignee: Lord CorporationInventor: Dilipkumar N. Shah
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Patent number: 4775718Abstract: An elastomeric homopolymer or copolymer is reacted with or, in effect, grafted onto an unsaturated polyester and the reaction product or graft polymer may then be used in a thermosetting unsaturated polyester resin composition. The chemical linkage between the elastomeric polymer and the unsaturated polyester is a cyclic structure comprising 6 carbon atoms. The chemical bond is achieved by first treating the elastomeric polymer to incorporate a conjugated diolefin structure and then adding the conjugated diolefin group to an ethylenically unsaturated group in the polyester or a monomeric dienophile. When added to a monomeric dienophile, the polyester is then grafted onto the elastomeric polymer at the site of the monomeric dienophile. The chemical linkage or bonding occurs through a 4+2 Diels Alder addition.Type: GrantFiled: December 31, 1986Date of Patent: October 4, 1988Assignee: Shell Oil CompanyInventor: Antonius A. Broekhuis
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Patent number: 4771085Abstract: A printable dielectric composition comprising finely divided particles of talc and/or mica dispersed in a curable liquid composition containing acrylated rubber modified epoxy resin oligomer, acrylated polydiene oligomer and alkyl acrylate.Type: GrantFiled: December 3, 1987Date of Patent: September 13, 1988Assignee: E. I. Du Pont de Nemours and CompanyInventor: Christina N. Lazaridis
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Patent number: 4761435Abstract: Ultraviolet-curable ethylenically unsaturated liquid coating composition are disclosed which consist essentially of:1--polyethylenically unsaturated material in which the ethylenically unsaturated groups are polymerizable groups which are not (meth)acrylate groups;2--a polyamine resin, preferably a polytertiary amine resin; and3--an aryl ketone photosensitizer.Type: GrantFiled: October 3, 1986Date of Patent: August 2, 1988Assignee: DeSoto, Inc.Inventors: Edward J. Murphy, Ronald S. Conti
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Patent number: 4727097Abstract: A highly reactive, water-absorptive resin is prepared by (1) impregnating a highly water-absorptive resin having carboxyl or carboxylate groups and a water content of 50 percent by weight or lower with a hydrophilic polymer or monomer having a reactive group and (2) polymerizing said monomer or crosslinking said polymer with a crosslinking agent.Type: GrantFiled: March 4, 1986Date of Patent: February 23, 1988Assignee: Kao CorporationInventors: Takatoshi Kobayashi, Harumasa Yamasaki, Yuzo Sumida
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Patent number: 4687812Abstract: A crosslinkable composition of matter is provided, which comprises first and second chain extended diepoxide resins, one or both of which are modified by reaction with hydroxy functional secondary amine and one or both of which are modified by reaction with certain secondary amine terminated or carboxy terminated butadiene acrylonitrile copolymer resin. The first resin, diene functional aminoepoxy resin, and the second resin, blocked dieneophile functional aminoepoxy resin, are co-reactive at elevated cure temperature. The diene functional aminoepoxy resin comprises the reaction product of diepoxide with amine functional diene chain extending reactant and, optionally, monofunctional end-capping reactant such as monohydroxy functional diene, and certain modifying agents.Type: GrantFiled: July 28, 1986Date of Patent: August 18, 1987Assignee: E. I. Du Pont de Nemours and CompanyInventors: Ray A. Dickie, Saiyed B. A. Oaderi
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Patent number: 4654233Abstract: A coating composition is provided. The coating composition is a curable blend of ethylenically unsaturated polyester and ethylenically unsaturated thermoplastic polymers. The composition is capable of providing a thermoplastic, soluble, sandable, intermediate-stage coating and, when cured, a final stage coating which is unaffected by acetone placed on the final stage coating for two hours at 22.degree. C., has a percent haze value of 15% or less, and is unaffected when subjected to a Wet Print Test.Type: GrantFiled: November 21, 1984Date of Patent: March 31, 1987Assignee: Minnesota Mining and Manufacturing CompanyInventors: Richard J. Grant, Gilbert C. Johnson, Heather V. Landin
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Patent number: 4619953Abstract: Low styrene emission vinyl ester resin compositions containing a polyacrylate as an adhesion promoter. Said VER composition exhibits desirable physical properties such as low styrene emission and excellent adhesive bond strength.Type: GrantFiled: September 9, 1985Date of Patent: October 28, 1986Assignee: The Dow Chemical CompanyInventors: John A. Schols, Kee C. Yu
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Patent number: 4617348Abstract: A crosslinkable composition of matter is provided, which comprises first and second chain extended diepoxide resins, one or both of which are modified by reaction with hydroxy functional secondary amine and one or both of which are modified by reaction with certain secondary amine terminated or carboxy terminated butadiene acrylonitrile copolymer resin. The first resin, diene functional aminoepoxy resin, and the second resin, blocked dieneophile functional aminoepoxy resin, are co-reactive at elevated cure temperature. The diene functional aminoepoxy resin comprises the reaction product of diepoxide with amine functional diene chain extending reactant and, optionally, monofunctional end-capping reactant such as monohydroxy functional diene, and certain modifying agents.Type: GrantFiled: December 10, 1984Date of Patent: October 14, 1986Assignee: Ford Motor CompanyInventors: Ray A. Dickie, Saiyed B. A. Qaderi
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Patent number: 4604230Abstract: A novel adhesive exhibiting low outgassing upon exposure to high temperature is disclosed. The instant adhesive comprises: (a) a soluble polyimide resin, (b) a solvent for said polyimide resin, (c) a tackifier, (d) an epoxy resin, (e) a hardener for said epoxy resin, (f) a catalyst which catalyzes the reaction between the epoxy and hardener, (g) a cross-linking agent reactive with the polyimide solvent of (b), (h) a catalyst which accelerates the reaction between (b) and (g), and (i) a filler material. Optionally, the adhesive may also contain a conductive material. A process for making the adhesive is also disclosed.Type: GrantFiled: October 15, 1984Date of Patent: August 5, 1986Assignee: Stauffer Chemical CompanyInventors: Jagadish C. Goswami, Joseph A. Aurichio, Joseph R. Zingaro
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Patent number: 4593051Abstract: This invention is directed to photocopolymerizable compositions comprising an epoxide containing two or more epoxy groups, a polymer/poly (active hydrogen) organic compound and a photoinitiator. The cured coating compositions exhibit a clear appearance, good water resistance and can have utility as automotive finishes, can finishes, appliance finishes, general metal finishes, adhesives, printing inks, and the like.Type: GrantFiled: February 7, 1983Date of Patent: June 3, 1986Assignee: Union Carbide CorporationInventor: Joseph V. Koleske
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Patent number: 4567237Abstract: Ethylenically unsaturated polyesters are provided. These ethylenically unsaturated polyesters are the reaction product of (a) a polyhydroxy polyester material that is the reaction product of at least one organic dicarboxylic acid, at least one diepoxide, and, optionally, monocarboxylic acid and/or monoepoxide with (b) a polymerizable ethylenically unsaturated compound having a functional group reactive with the hydroxyl groups of the polyhydroxy polyester. This product is particularly useful as a protective coating material.Type: GrantFiled: November 21, 1984Date of Patent: January 28, 1986Assignee: Minnesota Mining and Manufacturing CompanyInventors: Gilbert C. Johnson, Heather V. Landin
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Patent number: 4563501Abstract: A cathode-precipitating electrodeposition coating composition consisting essentially of (A) 100 parts of a high-molecular-weight compound having a molecular weight of 500 to 10,000 and containing an amino group and a carbon-carbon double bond, (B) 3 to 200 parts by weight of a reaction product obtained by reacting an unsaturated carboxylic acid having 3 or 4 carbon atoms with the terminal glycidyl group of a glycidyl compound obtained by reacting a bisphenol with epichlorohydrin, and (C) 0.2 to 20 parts by weight of an oil-soluble manganese salt of a monoester of a 1,2-dicarboxylic acid or a manganese salt of sulfonated or maleinized polybutadiene having a molecular weight of 300 to 3,000.Type: GrantFiled: May 10, 1983Date of Patent: January 7, 1986Assignee: Nippon Oil Company, Ltd.Inventors: Yutaka Otsuki, Yoshihiko Araki, Hiroyoshi Omika, Hajime Hara, Kazuho Aoyama
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Patent number: 4543406Abstract: A cathode-precipitating electrodeposition coating having excellent low-temperature curability, said composition consisting essentially of(A) 100 parts by weight of a high molecular compound having a molecular weight of 500 to 10,000 and containing carbon-carbon double bonds with an iodine value of 50 to 500 and 30 to 300 millimoles of amino groups per 100 g,(B) 10 to 200 parts by weight of a product of reaction of a diglycidyl compound represented by the general formula ##STR1## wherein R.sub.1, R.sub.2 and R.sub.Type: GrantFiled: October 15, 1984Date of Patent: September 24, 1985Assignees: Nippon Paint Co., Ltd., Nippon Oil Company, Ltd.Inventors: Yutaka Otsuki, Hiroyoshi Omika, Akio Oshima, Yoshihiko Araki, Yasuyuki Tsuchiya
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Patent number: 4537805Abstract: This invention relates to a thermosetting plastisol dispersion composition comprising(1) at least one copolymer of acrylonitrile-butadiene-styrene (ABS) in powder form, which is insoluble in the reactive plasticizer at room temperature and plasticizable at a temperature at or above the fluxing temperature;(2) a liquid reactive plasticizer member of the group consisting of (a) at least one epoxide resin having an average of more than one epoxide group in the molecule, (b) at least one liquid monomer, oligomer or prepolymer characterized by (1) containing at least one ethylenically unsaturated group and (2) capable of solvating the ABS at the fluxing temperature, and (c) a mixture of (a) and (b); and(3) an effective amount of either a thermal initiator or photoinitiator for plasticizers present in the composition.The plastisol dispersion after fluxing can form a thermoset sealant, coating or adhesive after the crosslinking reaction.Type: GrantFiled: March 26, 1984Date of Patent: August 27, 1985Assignee: W. R. Grace & Co.Inventor: Shiow C. Lin
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Patent number: 4532299Abstract: A method for flexibilizing an epoxy resin is disclosed which comprises (a) preparing a dicarboxy-terminated prepolymer by reacting a carboxylic anhydride with a polybutadiene having a minor amount of pendant vinyl groups at a temperature from about 125.degree. to about 140.degree. F.; (b) reacting the prepolymer with an excess of liquid epoxy resin at a temperature from about 180.degree. to about 200.degree. F.; (c) adding a vinyl monomer in an amount of about 2% to about 25% of the mixture; and (d) adding epoxy and vinyl polymerization catalysts to cure the mixture.Type: GrantFiled: January 21, 1983Date of Patent: July 30, 1985Assignee: Ameron, Inc.Inventor: James A. Seneker
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Patent number: 4530962Abstract: An elastomer-modified unsaturated polymer comprises an unsaturated polyester or vinyl ester polymer modified by a low molecular weight elastomer. The elastomer has terminal groups provided by an epoxy resin which render it compatible with the unsaturated polymer. These elastomer-modified unsaturated polymers are useful for providing resin compositions which include a cross-linking agent for the unsaturated polymer. The elastomer is soluble in the resin composition, which is curable to provide an unsaturated resin matrix having particles of the modifying elastomer dispersed therein.Type: GrantFiled: November 9, 1982Date of Patent: July 23, 1985Assignee: Scott Bader Company LimitedInventor: Ian J. Alexander
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Patent number: 4528307Abstract: This invention relates to radiation hardenable primers based on prepolymers containing (meth) acryloyl groups and conventional auxiliary agents. The primers are characterized in that they contain organic and/or inorganic fibres having a fibre length distribution curve reaching its maximum in the region of from 50 to 600 .mu.m. These primers are suitable for coating articles which have absorbent surfaces, in particular for the continuous coating of wood-concrete articles such as wood-concrete boards.Type: GrantFiled: September 15, 1983Date of Patent: July 9, 1985Assignee: Bayer AktiengesellschaftInventors: Karl Fuhr, Hans-Joachim Freier
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Patent number: 4496692Abstract: Improved molding composition comprising (1) polyvinyl chloride, which is blended with a dehydrochlorinating agent such as a stannous salt; (2) a free-radically polymerizable monomer and/or macromer, wherein the monomer contains at least one terminal CH.sub.2 .dbd.C< group per molecule and the macromer contains at least one double bond in the polymeric backbone; (3) an ionically polymerizable monomer and/or macromer containing the oxirane group ##STR1## with an optional curing agent; (4) a heterofunctional monomer containing at least one oxirane group and at least one CH.sub.2 .dbd.C< group per molecule; and (5) a free radical initiator results in an improvement in thermo-mechanical properties.Type: GrantFiled: December 30, 1983Date of Patent: January 29, 1985Assignee: The B. F. Goodrich CompanyInventors: Changkiu K. Riew, Frank H. Howard
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Patent number: 4467071Abstract: Structural adhesive systems having improved heat resistance comprising a solution or dispersion of a polymeric material in a monomer copolymerizable therewith, an unsaturated organophosphorus partial ester and an epoxy resin are disclosed.Type: GrantFiled: September 13, 1982Date of Patent: August 21, 1984Assignee: Lord CorporationInventor: Terrance H. Dawdy
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Patent number: 4463134Abstract: Modified epoxy resin compositions having excellent flexibility and excellent compatibility with conventional epoxy resins as well as exhibiting the original properties of the epoxy resin before being modified such as mechanical strength, adhesion, heat resistance are disclosed and chemical resistance, which are obtained by treating an epoxy resin with at least one modified adduct [D] of a conjugated diene polymer or copolymer which has an imido bond and/or amido bond and a semi-ester structure and has an acid value owing to a free carboxyl group of 5 to 100. The modified adduct is obtained by reacting an adduct [A] of a polymer of a conjugated diene having a number average molecular weight of 300 to 20,000 or a copolymer of the conjugated diene and a vinyl monomer with an .alpha.,.beta.-unsaturated dicarboxylic acid or its anhydride, with a compound [B] containing one primary amino group in the molecule and a compound [C] containing a hydroxy group in the molecule.Type: GrantFiled: December 22, 1981Date of Patent: July 31, 1984Assignees: Sumitomo Chemical Company, Limited, Tohto Kasei Co., Ltd.Inventors: Minoru Hino, Takao Oshima, Akihiro Tachibana
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Patent number: 4446258Abstract: Aqueous compositions suitable for sanitary can coatings comprising the neutralized water dispersible ionic polymer product of the reaction of an epoxy resin with acid polymer, and a different resin which is not necessarily self-dispersible in water, as well as several methods of preparing such compositions, are disclosed. The second resin which is not necessarily self-dispersible in water is introduced either preformed at any stage or is prepared, in situ, in the presence of the epoxy resin esterified with acid polymer either before the ionic epoxy resin-acid polymer product is dispersed in water. The epoxy resin-acid polymer product acts as a polymeric surfactant capable of keeping even a normally non self-dispersible second polymer in stable dispersion in water.Type: GrantFiled: December 30, 1982Date of Patent: May 1, 1984Assignee: Mobil Oil CorporationInventors: Shaw C. Chu, Arthur T. Spencer
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Patent number: 4444923Abstract: An improved process for preparing epoxy acrylate dispersions from the reaction product of an epoxy resin and carboxyl containing polymer in the presence of tertiary amine in which the carboxyl containing polymer is formed, in situ, in the presence of a solvent solution of the epoxy resin and then subjected to the esterification reaction which can be conducted in a single pot.Type: GrantFiled: December 30, 1982Date of Patent: April 24, 1984Assignee: Mobil Oil CorporationInventor: William H. McCarty
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Patent number: 4436869Abstract: A process for the preparation of moldings, in particular resilient elements, which by virtue of a densified surface zone with substantially closed cells, have only a low water absorption, wherein a mixture comprising:(a) 100 parts by weight of an NCO-containing prepolymer, having an NCO content of from 3 to 6% by weight and based on organic diisocyanates and substantially linear polyester-polyols or polytetramethylene ether glycol,(b) from 0.5 to 1.6 parts by weight of water,(c) one or more catalysts, preferably a tertiary amine, in an amount of from 0.01 to 2.0 parts by weight and(d) assistants, with or without additives, is reacted in a closed mold, while undergoing densification, the surface temperature of the inner wall of the mold being from 50.degree. to 70.degree. C.Type: GrantFiled: March 30, 1982Date of Patent: March 13, 1984Assignee: Elastogran GmbHInventors: Otmar Zipp, Heinz Bollmann, Herbert Stutz, Wolfgang Scholz
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Patent number: 4426496Abstract: Thermosettable resin compositions are disclosed which comprise a mixture of (1) an unsaturated polymerizable monomer, (2) an unsaturated polymerizable resin selected from (a) unsaturated polyester or polyesteramide resins, (b) vinyl ester resins and (c) dicyclopentadiene modified unsaturated polyester of polyesteramide resins and (3) a poly(allyl)poly(alkenylphenol).Type: GrantFiled: October 28, 1982Date of Patent: January 17, 1984Assignee: The Dow Chemical CompanyInventor: Robert E. Hefner, Jr.
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Patent number: 4426243Abstract: A polymerizable mixture for adhesive bonding is disclosed. The polymerizable mixture comprises a polymerizable acrylic-based material, a polymerizable epoxide-based material and a bifunctional molecular material reactable with said acrylic-based material and said epoxide-based material.Type: GrantFiled: December 1, 1981Date of Patent: January 17, 1984Assignee: Illinois Tool Works Inc.Inventor: Paul C. Briggs
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Patent number: 4400313Abstract: An improvement in the process of encapsulating waste materials in aqueous liquid or finely divided, dry solid form, in liquid thermosettable resins of the group consisting of vinyl ester resins, unsaturated polyester resins, and mixtures thereof, which comprises increasing the amount of waste material incorporated in a given amount of resin by adding thereto a water-soluble polymeric substance containing a carbon chain having a plurality of --COOH groups or derivatives thereof.Type: GrantFiled: June 30, 1980Date of Patent: August 23, 1983Assignee: The Dow Chemical CompanyInventors: Keith Roberson, Harold E. Filter
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Patent number: 4399241Abstract: Provides new and improved water-reducible coating compositions and methods of making them. Three preferred processes are disclosed. These differ in the manner of incorporating and chemical nature of an extender polymer.Broadly, the process of the invention is one for forming an aqueous dispersion of a fluent resinous composition ofa. a mixture in an organic solvent of(i) an ionizable graft polymer of an epoxy resin and an addition polymerized resin, the addition polymerized resin being bonded to aliphatic backbone carbon atoms of the epoxy resin by carbon-to-carbon bonds, and(ii) an extender resin;b. an aqueous vehicle, andc. an ionizing agent;the ionization present from said combined components being sufficient to establish the components as a dispersion in the aqueous vehicle, and then addition polymerizing a quantity of addition polymerizable monomer, under addition polymerizing conditions, in said aqueous dispersion, the aqueous dispersion serving as a vehicle therefor.Type: GrantFiled: March 21, 1980Date of Patent: August 16, 1983Assignee: SCM CorporationInventors: Vincent W. Ting, James T. K. Woo, Richard M. Marcinko
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Patent number: 4389512Abstract: Cycloalphatic acrylate compositions and methods of making them are disclosed. The compositions are mixtures containing dicyclopentadiene (meth) acrylate and (meth) acrylates such as the mono and di (meth) acrylates of tri, and tetracyclopentadiene and a mixture of the copolymers of (meth) acrylic acid with adducts of cyclopentadiene with isoprene and/or piperylene and a mixture of poly (meth) acrylates having the repeating unit ##STR1## where R.sup.1 is hydrogen or ##STR2## R.sup.2 is CH.sub.2 .dbd.CZ--C(O)--O-- Z is H, or methyln is 0, 1 or 2 andm is 0 or 1 and when m is 0 there isa double bond present.The compositions are useful to make crosslinkable blends with unsaturated resins or monomers and to make laminates.Type: GrantFiled: May 29, 1981Date of Patent: June 21, 1983Assignee: The Dow Chemical Co.Inventors: Hans R. Friedli, Donald L. Nelson, John L. Massingill, Jr.
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Patent number: 4387182Abstract: Cycloalphatic acrylate compositions and methods of making them are disclosed. The compositions are mixtures containing dicyclopentadiene (meth) acrylate and (meth) acrylates such as the mono and di (meth) acrylates of tri, and tetracyclopentadiene and a mixture of the copolymers of (meth) acrylic acid with adducts of cyclopentadiene with isoprene and/or piperylene and a mixture of poly (meth) acrylates having the repeating unit ##STR1## where R.sup.1 is hydrogen or ##STR2## R.sup.2 is CH.sub.2 .dbd.CZ--C(O)--O-- Z is H, or methyln is 0, 1 or 2 andm is 0 or 1 and when m is 0 there is a double bond present.The compositions are useful to make cross-linkable blends with unsaturated resins or monomers and to make laminates.Type: GrantFiled: May 29, 1981Date of Patent: June 7, 1983Assignee: The Dow Chemical Co.Inventors: Hans R. Friedli, Donald L. Nelson, John L. Massingill, Jr.
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Patent number: 4362848Abstract: Cycloalphatic acrylate compositions and methods of making them are disclosed. The compositions are mixtures containing dicyclopentadiene (meth) acrylate and (meth) acrylates such as the mono and di (meth) acrylates of tri, and tetracyclopentadiene and a mixture of the copolymers of (meth) acrylic acid with adducts of cyclopentadiene with isoprene and/or piperylene and a mixture of poly (meth) acrylates having the repeating unit ##STR1## Where R.sup.1 is hydrogen or ##STR2## R.sup.2 is CH.sub.2 .dbd.CZ--C(O)--O-- Z is H, or methyln is 0, 1 or 2 andm is 0 or 1 and when m is 0 there isa double bond present.The compositions are useful to make cross-linkable blends with unsaturated resins or monomers and to make laminates.Type: GrantFiled: May 29, 1981Date of Patent: December 7, 1982Assignee: The Dow Chemical Co.Inventors: Hans R. Friedli, Donald L. Nelson, John L. Massingill, Jr.
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Patent number: 4360628Abstract: Solid copolymer tackifying resins based on dicyclopentadiene, a vinylaromatic hydrocarbon and a benzene carrying 1 to 3 lower alkyl, hydroxyl or halogen substituents and adhesive formulations containing these resins.Type: GrantFiled: January 19, 1981Date of Patent: November 23, 1982Assignee: National Starch and Chemical CorporationInventors: Yves Runavot, Georges Billault, Jacques Salvetat
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Patent number: 4336349Abstract: Chlorinated cycloaliphatic (meth) acrylate compositions are prepared by the reaction of chlorine at a temperature in the range from -30.degree. C. to 50.degree. C. with compositions made by reacting (meth) acrylic acid with crude dicyclopentadiene in the presence of a Friedel-Crafts catalyst such as BF.sub.3. The chlorinated compositions have a pleasant fruity odor and are useful to make homopolymers or copolymers which find use as metal coatings, inks, ultraviolet light curable coatings and the like.Type: GrantFiled: December 22, 1980Date of Patent: June 22, 1982Assignee: The Dow Chemical CompanyInventors: Hans R. Friedli, Clinton J. Boriack
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Patent number: 4319009Abstract: Cycloalphatic acrylate compositions and methods of making them are disclosed. The compositions are mixtures containing dicyclopentadiene (meth) acrylate and (meth) acrylates such as the mono and di (meth) acrylates of tri, and tetracyclopentadiene and a mixture of the copolymers of (meth) acrylic acid with adducts of cyclopentadiene with isoprene and/or piperylene and a mixture of poly (meth) acrylates having the repeating unit ##STR1## where R.sup.1 is hydrogen or ##STR2## R.sup.2 is CH.sub.2 .dbd.CZ-C(O)--O-- Z is H, or methyln is 0, 1 or 2 andm is 0 or 1 and when m is 0 there isa double bond present.The compositions are useful to make crosslinkable blends with unsaturated resins or monomers and to make laminates.Type: GrantFiled: October 13, 1978Date of Patent: March 9, 1982Assignee: The Dow Chemical CompanyInventors: Hans R. Friedli, Donald L. Nelson, John L. Massingill, Jr.
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Patent number: 4284551Abstract: Tertiary aromatic amines derived from para-aminophenethanol act as accelerators for the peroxide catalyzed polymerization of vinyl monomers, especially methacrylates and acrylates, and for the curing of unsaturated polyesters. The amines are characterized by generally high reactivity and low toxicity, and by their yielding polymers of high strength and low color, and are thereby particularly suited for use in polymerizable or curable formulations employed in the filling and restoration of human teeth, in the preparation of cold-curing denture base materials for fabricating or repairing dentures and in the cementing of bone.Type: GrantFiled: November 30, 1979Date of Patent: August 18, 1981Assignee: American Dental Association Health FoundationInventor: Harold Argentar
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Patent number: 4271275Abstract: Novel curable fluoropolymer compositions containing fluoroelastomer, peroxide, co-agent, conventional additives, e.g., pigments and fillers, and also containing oxirane as the acid acceptor.Type: GrantFiled: December 14, 1979Date of Patent: June 2, 1981Assignee: E. I. Du Pont de Nemours and CompanyInventor: James D. MacLachlan