At Least One Reactant Contains A Three-membered Heterocyclic Ring Having Two Carbon And One Oxygen Atoms, E.g., Oxirane, Etc. Patents (Class 528/393)
  • Patent number: 4841017
    Abstract: Disclosed as a polyether compound having ether groups and vinyl double bonds represented by formula (I) ##STR1## and an epoxy resin represented by formula (II) ##STR2## wherein R.sup.1 represents a residue group of an organic compound having l active hydrogen atoms, n1 through nl each represents 0 or an integer of from 1 to 100, the sum of integers represented by n1 through nl is from 1 to 100, and l represents an integer of from 1 to 100, and A represents from 1 to 100, and A represents ##STR3## or a mixture of ##STR4## wherein R.sup.2 represents a residue group of mono epoxy compound, and B represents ##STR5## or a mixture of ##STR6## wherein X represents a ##STR7## group, wherein R.sup.3 represents a hydrogen atom, an alkyl group, an alkyl carbonyl group, or an arylcarbonyl group, provided that the epoxy resin represented by formula (II) contains at least one ##STR8## group: In a further aspect, the invention relates to processes for production thereof.
    Type: Grant
    Filed: March 11, 1988
    Date of Patent: June 20, 1989
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Takaaki Murai, Katsuhisa Sakai
  • Patent number: 4812488
    Abstract: This invention is directed to photocopolymerizable compositions comprising a poly (active hydrogen) organic compound, a photoinitiator and, as a reactive diluent, a substituted cycloaliphatic monoepoxide. The photocopolymerizable compositions have low viscosity and can be applied to suitable substrates by conventional methods and, after curing, provide excellent pressure sensitive and heat-activated adhesive coatings.
    Type: Grant
    Filed: November 6, 1985
    Date of Patent: March 14, 1989
    Assignee: Union Carbide Corporation
    Inventors: Joseph V. Koleske, George T. Kwiatkowski
  • Patent number: 4791154
    Abstract: A composition comprising an epoxy resin and an aromatic azopolyamine curing agent is described. The use of azopolyamine curing agents in reactive monomer-diluted systems results in a high-modulus cured epoxy system.
    Type: Grant
    Filed: November 30, 1987
    Date of Patent: December 13, 1988
    Assignee: Shell Oil Company
    Inventors: Larry S. Corley, Donald R. Gehring
  • Patent number: 4694067
    Abstract: A rubber composition for dust cover boots comprising a copolymer rubber composed of 10 to 60 mole % of epichlorohydrin, 30 to 90 mole % of propylene oxide or both propylene oxide and ethylene oxide with the propylene oxide/ethylene oxide mole ratio being at least 1, and 0 to 15 mole % of an unsaturated epoxide, and a vulcanization agent for the copolymer rubber.
    Type: Grant
    Filed: July 16, 1985
    Date of Patent: September 15, 1987
    Assignee: Nippon Zeon Co., Ltd.
    Inventors: Akio Maeda, Takeshi Chida, Hirokatsu Seya
  • Patent number: 4612352
    Abstract: Water-soluble or water-dispersible graft polymers comprising at least 20% by weight, based on said graft polymer, of a hydrophilic graft constituent bonded to a carbon atom and at least one hydrophobic radical which is bonded to the graft constituent via a polyglycol ether chain, the polyglycol ether chain containing 2 to 200 ##STR1## groups. These graft polymers can be used individually, as mixtures or in combination with other active substances as, for example, antifoams, antistatic agents, builders, emulsifiers, padding assistants, wetting agents, paper deaerators, sludge dewatering assistants, textile assistants, greying inhibitors or detergents.
    Type: Grant
    Filed: November 19, 1984
    Date of Patent: September 16, 1986
    Assignee: Ciba-Geigy Corporation
    Inventors: Paul Schafer, Heinz Abel, Christian Guth, Albert Stehlin
  • Patent number: 4607092
    Abstract: This invention is directed to organophosphorus compounds useful as epoxy curing agents and adhesion promoters.
    Type: Grant
    Filed: June 17, 1985
    Date of Patent: August 19, 1986
    Assignee: Ford Motor Company
    Inventors: Milton D. Johnson, Mohinder S. Chattha
  • Patent number: 4567237
    Abstract: 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: Grant
    Filed: November 21, 1984
    Date of Patent: January 28, 1986
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Gilbert C. Johnson, Heather V. Landin
  • Patent number: 4558115
    Abstract: Compositions comprising a material containing (a) alkenyl phenyl cyanate groups, (b) a material containing epoxide groups and optionally any one or more of (c) an aromatic polycyanate, (d) a polymaleimide or (e) a polymerizable ethylenically unsaturated aromatic material are curable to products having excellent mechanical, thermal and chemical resistant properties.
    Type: Grant
    Filed: March 11, 1985
    Date of Patent: December 10, 1985
    Assignee: The Dow Chemical Company
    Inventor: Robert E. Hefner, Jr.
  • Patent number: 4548752
    Abstract: Improved rigid urethane and isocyanurate foam compositions having improved fire resistance are described. The urethane foams are based on furan compositions and are chiefly made from adding propylene oxide to bis(hydroxymethyl)furan.
    Type: Grant
    Filed: November 14, 1983
    Date of Patent: October 22, 1985
    Assignee: QO Chemicals, Inc.
    Inventor: William J. Pentz
  • Patent number: 4537946
    Abstract: A novel process for the preparation of isomelamines of the formula I, ##STR1## which is characterized in that an N-cyano-N-(ar or cyclo)alkylcarboxylic acid amide or N-cyano-N-allylcarboxylic acid amide of the formula II or III ##STR2## is reacted with aqueous sodium hydroxide solution, potassium hydroxide solution or ammonia solution or a primary aliphatic or cycloaliphatic amine in a solvent or with a primary aliphatic alcohol in the presence of a catalytic amount of a basic compound in a temperature range from -20.degree. C. to 200.degree. C., at least 3 hydroxyl or amino group equivalents being used per 3 carboxylic acid amide group equivalents.The isomelamines prepared by the process according to the invention are valuable curing agents for epoxide resins.
    Type: Grant
    Filed: November 28, 1984
    Date of Patent: August 27, 1985
    Assignee: Ciba-Geigy Corporation
    Inventors: Friedrich Lohse, Helmut Zondler
  • Patent number: 4503211
    Abstract: An epoxy resin latently curable composition including a novel curing agent comprising the liquid salt of a substituted pentafluoroantimonic acid and an aromatic amine selected from the group consisting of aniline and a hindered amine has a desirably long pot life yet cures rapidly with heating to a cured composition.
    Type: Grant
    Filed: May 31, 1984
    Date of Patent: March 5, 1985
    Assignee: Minnesota Mining and Manufacturing Co.
    Inventor: Janis Robins
  • Patent number: 4500562
    Abstract: A method and apparatus for forming an improved poly-p-xylylene film. Solid di-para-xylylene dimer is sublimed in a sublimation furnace at approximately 100.degree. to 200.degree. C. and subsequently conducted to a pyrolysis furnace where it is pyrolyzed to the diradical p-xylylene monomer while in the vapor state at approximately 600 degrees C. The diradical monomer is then introduced into a deposition chamber for deposition onto a suitable substrate. The deposition chamber includes electrodes for producing a low pressure plasma through which the diradical monomer passes prior to deposition. The interaction of the diradical monomer with the low pressure plasma results in the formation of poly-p-xylylene film which is exceptionally hard and thermally stable.
    Type: Grant
    Filed: March 2, 1983
    Date of Patent: February 19, 1985
    Assignee: The United States of America as represented by the United States Department of Energy
    Inventors: Randy K. Jahn, Raimond Liepins
  • Patent number: 4500687
    Abstract: Excellent and very high quality impact-resistant polymer products products are comprised of particular polyether elastomer constituents which modify and attribute many desirable properties and characteristics to the interpolymerized end product; impact styrene polymers being especially advantageous varieties thereof. In-situ polymerization, with specific coordination catalyst systems, is followed to form polyether polymers of epoxidized monomer constituents provided directly dissolved (or dispersed) in the major addition-polymerizable monomer utilized. The rubbery polyether elastomer so made is then interpolymerized with the major monomer to provide the advantageous high impact end product.
    Type: Grant
    Filed: June 18, 1981
    Date of Patent: February 19, 1985
    Assignee: The Dow Chemical Company
    Inventor: David L. Wolfe
  • Patent number: 4478980
    Abstract: There is disclosed a rubbery composition comprising a blend of between 95/5 and 5/95 weight percent of (1) a rubbery interpolymer consisting of (a) at least 80 weight percent of at least one .alpha.-olefin containing from 5 to 10 carbon atoms and (b) up to 20 weight percent of a nonconjugated polyene containing from 5 to 30 carbon atoms with (2) a saturated polymer of an .alpha.-olefin oxide prepared from at least one monomer having the structure: ##STR1## wherein R.sub.1 and R.sub.2 are selected from the group consisting of hydrogen or a lower alkyl radical containing from 1 to 8 carbon atoms and R.sub.3 and R.sub.4 are selected from the group consisting of hydrogen, a lower alkyl radical containing from 1 to 8 carbon atoms and an alkoxyalkyl radical containing up to 12 carbon atoms, an aryl radical, a haloalkyl radical containing from 1 to 12 carbon atoms and in which R.sub.3 and R.sub.
    Type: Grant
    Filed: September 13, 1982
    Date of Patent: October 23, 1984
    Assignee: The Goodyear Tire & Rubber Company
    Inventors: Joginder Lal, Paul H. Sandstrom
  • Patent number: 4423206
    Abstract: A polymerization process for vicinal alkylene oxides and a catalyst for said polymerization process where the catalyst comprises a composition prepared by contacting an alkyl aluminum compound with an organic nitrogen base compound selected from secondary nitrogen-containing compounds having basicity less than or about equal to the basicity of dimethylamine, with a .beta.-diketone and with water where the components are combined in prescribed molar ratios. The molecular weight of the resultant polymers produced in a process utilizing such a catalyst may be controlled by adjusting the ratio of the secondary amine component and very high molecular weight polymers may be obtained, as determined by their intrinsic viscosities. The very high molecular weight polymeric products are useful as elastomers and as thickeners for various aqueous or organic solutions.
    Type: Grant
    Filed: June 21, 1982
    Date of Patent: December 27, 1983
    Assignee: The Dow Chemical Co.
    Inventors: David L. Wolfe, Frederick P. Corson
  • Patent number: 4421806
    Abstract: Filament-wound composite bodies are disclosed. These bodies contain filament-wound fibers and resin. The resin, when cured, has a density of less than 1.05 g/cc and exhibits a water pick up of less than 1% by weight. When uncured, the resin contains an aromatic vinyl hydrocarbon monomer and as its major component poly(1,2-butadiene), carboxy-terminated poly(1,2-butadiene) or mixtures thereof and has a viscosity of less than 2000 cps at 45.degree. C. These filament-wound bodies advantageously are embodied as rocket motor cases.
    Type: Grant
    Filed: August 13, 1981
    Date of Patent: December 20, 1983
    Assignee: Lockheed Missiles & Space Company, Inc.
    Inventors: Burton S. Marks, Richard E. Mauri, Gazel W. Watsey
  • Patent number: 4410680
    Abstract: A curable thermosetting resin, especially suitable for RIM applications, comprising a blend of(a) 100 parts by weight of a polyepoxide, particularly a normally liquid polyepoxide and more particularly a glycidyl polyether of a polyhydric phenol,(b) from about 10 to about 200 parts by weight of at least one ethylenically unsaturated monomer, especially an aromatic monomer, and preferably styrene,(c) a curing amount of an aliphatic or cycloaliphatic polyfunctional amine or a polyamide, and(d) an effective amount of an amine-compatible free-radical initiator.
    Type: Grant
    Filed: November 4, 1982
    Date of Patent: October 18, 1983
    Assignee: Shell Oil Company
    Inventors: Thomas F. Brownscombe, William W. C. Hart
  • Patent number: 4379908
    Abstract: The present invention provides an curable composition comprising (1) at least one epoxy compound containing at least one vicinal-epoxy groups, (2) a miscible amount of at least one ethylenically unsaturated monomer and (3) a curing amount of at least one catalyst selected from lithium or Group II metal salts of a non-nucleophilic acid.
    Type: Grant
    Filed: March 5, 1982
    Date of Patent: April 12, 1983
    Assignee: Shell Oil Company
    Inventor: Thomas F. Brownscombe
  • Patent number: 4358477
    Abstract: The invention relates to a radiation curable liquid coating composition based on (A) an epoxy compound containing an acryloyl and/or methacryloyl group, (B) a cross-linking agent for the epoxy groups of component (A) and a photoinitiator. The invention also relates to a process for coating a substrate with such a composition, and to the substrate thus manufactured.
    Type: Grant
    Filed: September 5, 1979
    Date of Patent: November 9, 1982
    Assignee: Akzo N.V.
    Inventors: Arie Noomen, Johannes Mostert, Egbert Wolters
  • Patent number: 4352913
    Abstract: (Dimethylaminoalkyl)carboxylic and -carbamic acid esters and (dimethylaminoalkyl) ethers and ureas are compounds which are especially suitable for use as amine curing agents for polyepoxide compounds. They impart longer curing times to the curable mixtures and thus good processing properties, especially when the mixtures are used as adhesives. In addition, the mechanical properties are often improved. Further, these compounds afford advantages when used as curing agents on account of their low volatility.
    Type: Grant
    Filed: August 21, 1981
    Date of Patent: October 5, 1982
    Assignee: Ciba-Geigy Corporation
    Inventors: Helmut Zondler, Roland Moser
  • Patent number: 4350809
    Abstract: A process for the preparation of copolymers containing hydroxyl groups by radical reaction of(A) 10 to 30% by weight of at least one glycidyl ester containing 12 to 14 carbon atoms, of an aliphatic saturated monocarboxylic acid with a tertiary or quaternary .alpha.-carbon atom; and(B) 90 to 70% by weight of at least two unsaturated copolymerisable monomers, at least one of which contains at least one carboxyl group,wherein component (A) is introduced first to a reaction zone and is then reacted at a temperature of at least 140.degree. C. with component (B) and a radical initiator, the component (B) containing a monomer having carboxyl groups,wherein for the preparation of low-viscosity copolymers component (A) is reacted at 140 to 200.degree. C. by substance polymerisation until a degree of reaction of at least 95% is achieved, the component (B) containing at least 3.3% by weight of the monomer having carboxyl groups, and an article coated with a product of said process.
    Type: Grant
    Filed: October 17, 1980
    Date of Patent: September 21, 1982
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hannes Fischer, Helmut Plum
  • Patent number: 4306953
    Abstract: Photopolymerizable compositions using sulfonium salt photoinitiators to effect polymerization of cationically polymerizable monomers additionally include a stable free radical to reduce or eliminate the sulfur odor generated upon photodecomposition of the sulfonium salt photoinitiator. The stable free radicals are soluble in the polymerizable material and are stable in the composition at ambient temperatures. Especially useful is 2,2-diphenyl-1-picrylhydrazyl.
    Type: Grant
    Filed: November 5, 1979
    Date of Patent: December 22, 1981
    Assignee: American Can Company
    Inventor: Sheldon I. Schlesinger
  • Patent number: 4297385
    Abstract: Finely divided polyetherimide is provided which can be used in a variety of applications. These oligomers, in the form of fine powders, are particularly useful for coating wire by a powder coating technique.
    Type: Grant
    Filed: April 7, 1980
    Date of Patent: October 27, 1981
    Assignee: General Electric Company
    Inventors: Eugene G. Banucci, Edith M. Boldebuck
  • Patent number: 4271284
    Abstract: Poly(amine allyl halides) copolymer may be produced by mixing an amine compound and a mono-olefinic allyl type monohalide compound in the presence of an oxidized silicon catalyst.
    Type: Grant
    Filed: January 19, 1979
    Date of Patent: June 2, 1981
    Inventor: David H. Blount
  • Patent number: 4215203
    Abstract: Allyl halide-halohydrinamine copolymers may be produced by mixing an allyl halide and an amine compound with an oxidated silicon compound and then by adding a halohydrin while agitating for 10 to 60 minutes.
    Type: Grant
    Filed: October 30, 1978
    Date of Patent: July 29, 1980
    Inventor: David H. Blount
  • Patent number: 4205150
    Abstract: A liquid chloroprene polymer having substantially at least one carboxyl group in the molecule and having a number average molecular weight of about 500 to about 20,000 which is produced by(1) homopolymerizing a chloroprene monomer or(2) copolymerizing a chloroprene monomer with a monomer copolymerizable with a chloroprene monomer,in the presence of an organic solvent and about 0.5 to about 20 parts by weight of a mercaptocarboxylic acid per 100 parts by weight of the monomers. The liquid polymer is reacted with a polyvalent metal oxide or hydroxide to form a thermo-reversible elastomeric composition.
    Type: Grant
    Filed: April 10, 1978
    Date of Patent: May 27, 1980
    Assignee: Denki Kagaku Kogyo Kabushiki Kaisha
    Inventor: Kiyonobu Marubashi
  • Patent number: 4197382
    Abstract: A rubber composition for use as a cover of rubber pipes or hoses, comprising a terpolymer rubber composed of 35 to 80 mole% of epichlorohydrin, 15 to 50 mole% of ethylene oxide and 5 to 15 mole% of an unsaturated epoxide, and a di- or tri-mercapto-s-triazine as a vulcanization agent.
    Type: Grant
    Filed: January 3, 1979
    Date of Patent: April 8, 1980
    Assignee: Nippon Zeon Co. Ltd.
    Inventors: Hiroshi Fukushima, Akio Maeda, Masaaki Inagami, Kinro Hashimoto
  • Patent number: 4197389
    Abstract: A hardening agent for an aqueous epoxy resin composition comprising a reaction product of (a) at least one polyepoxide compound, (b) at least one polyalkylene polyether polyol and (c) at least one compound selected from the group consisting of aliphatic, cycloaliphatic and heterocyclic polyamine and wherein component (c) additionally may be reacted with (d) an unsaturated compound before or after the reaction with the adduct of components (a) and (b), process for preparing said hardening agent and hardenable film forming coating compositions comprising as essential ingredients said hardening agent, at least one polyfunctional epoxy compound (a) and water.
    Type: Grant
    Filed: July 12, 1978
    Date of Patent: April 8, 1980
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Wilhelm Becker, Horst Karasmann
  • Patent number: 4195167
    Abstract: Polymers which comprise polymer chains along which the proportion of mer units provided by a first heterocyclic monomer gradually increases in a given chain length as the proportion of mer units provided by a second heterocyclic monomer gradually decreases along said chain length. In one form, the portions of the polymers adjacent one end of the given chain lengths have about 100% of mer units provided by the first monomer and about 0% of mer units provided by the second monomer and the portions adjacent the other end of the given chain lengths have about 0% of mer units provided by the first monomer and about 100% of mer units provided by the second monomer. Additional forms of polymers are disclosed.
    Type: Grant
    Filed: November 9, 1978
    Date of Patent: March 25, 1980
    Assignee: Union Carbide Corporation
    Inventors: Robert J. Knopf, Kenneth L. Hoy
  • Patent number: 4157438
    Abstract: Poly(amine allyl halides) copolymer may be produced by mixing an amine compound and a mono-olefinic allyl type monohalide compound in the presence of an oxidized silicon catalyst.
    Type: Grant
    Filed: December 19, 1977
    Date of Patent: June 5, 1979
    Inventor: David H. Blount
  • Patent number: 4157428
    Abstract: New and useful blends of thermosetting resins with copolymers of certain amounts of ethylene with another monomer copolymerizable therewith to provide solid but flexible polymers, and a third monomer containing epoxy side groups, and optionally carbon monoxide, are provided. These blends result in performance unattainable with the thermosetting resin alone in terms of flexibility, toughness, and adhesion. Such blends may be used, for example, to produce flexible, semirigid or rigid films, coatings, fibers, foams or molded articles.
    Type: Grant
    Filed: March 4, 1977
    Date of Patent: June 5, 1979
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Clarence F. Hammer
  • Patent number: 4124760
    Abstract: Diepoxides which may be photopolymerized in the presence or absence of a photosensitizer contain a group having conjugated unsaturation attached to a nitrogen heterocycle, such as a hydantoin or barbituric acid residue, forming part of an advanced diepoxide. The resultant photopolymer may be crosslinked by heating in the presence of a curing agent for epoxide resins.The diepoxides are of use in the production of printing plates and printed circuits, especially multilayer printed circuits.
    Type: Grant
    Filed: July 13, 1977
    Date of Patent: November 7, 1978
    Assignee: Ciba-Geigy Corporation
    Inventors: George E. Green, Bernard P. Stark, John S. Waterhouse
  • Patent number: 4115295
    Abstract: Two-part polymerizable compositions are described which contain (a) organic material having epoxide functionality, (b) organic material having hydroxyl functionality, and (c) a catalyst comprising highly fluorinated aliphatic sulfonyl protonic acid or a compound capable of liberating such acid. The compositions polymerize essentially completely at room temperature (or at slightly elevated temperatures). The polymerized compositions have desirable dielectric properties and are therefore especially useful for potting electrical components.
    Type: Grant
    Filed: April 26, 1976
    Date of Patent: September 19, 1978
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Janis Robins, James E. Kropp, Chung I. Young
  • Patent number: 4107142
    Abstract: Epoxide materials suitable for use in flexible adhesives are prepared by reacting a diene, such as butadiene or isoprene, with an electron donor, typically an alkali metal, in the presence of a polyepoxide normally in a molar ratio diene:polyepoxide of less than 3:1. The polyepoxide is typically a conventional epoxy resin such as DGBA. The product normally separates into two phases, the upper of which comprises epoxy-terminated diene oligomers with degrees of polymerization of about 6 to 14. This separation may be avoided by incorporating a minor proportion of acrylonitrile into the product by addition to either the original diene or the anionic living polymer immediately before hydrolysis. The products may be cured with conventional epoxide curing agents to give an internally flexibilized adhesive having useful combinations of tensile and shear strengths.
    Type: Grant
    Filed: May 12, 1976
    Date of Patent: August 15, 1978
    Assignee: National Research Development Corporation
    Inventors: Anthony Vernon Cunliffe, Peter John Pearce, David Hugh Richards
  • Patent number: 4100112
    Abstract: Amine silicate compounds are formed by the chemical reaction of hydrated silica with an amine compound in the presence of a suitable alkali catalyst at a suitably elevated temperature, and then by reacting the resultant compounds with aldehydes, epoxys, organic dicarboxylic anhydrides, polycarboxylic acid compounds or carbon disulfide, thereby forming a resinous condensation product.
    Type: Grant
    Filed: May 19, 1977
    Date of Patent: July 11, 1978
    Inventor: David H. Blount