With Nitrogen-containing Reactant, Or Wherein The Poly 1,2-epoxy Reactant Contains A Nitrogen Atom Patents (Class 525/113)
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Patent number: 4288568Abstract: An elastomer containing chemically bonded metal atoms is prepared by reacting a diene elastomer such as a nitrile rubber with the reaction product of an epoxy resin and a metal containing polymer. The metal containing polymer is prepared by reacting a polycarboxylic acid and a metal complex which is a reaction product of tungsten carbonyl and/or molybdenum carbonyl with pyrrolidine.Type: GrantFiled: July 30, 1980Date of Patent: September 8, 1981Assignee: HitcoInventors: Kenneth W. Lewis, Robert C. Shaffer
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Patent number: 4285849Abstract: Ungelled amidation reaction products of a polycarboxyl-containing material and a polyamine having at least one ether group are produced. The ungelled products can be mixed with a crosslinking resin to provide a coating composition having good durability and stain-resistance.Type: GrantFiled: November 27, 1979Date of Patent: August 25, 1981Assignee: PPG Industries, Inc.Inventors: Rostyslaw Dowbenko, Karl F. Schimmel, Jerome A. Seiner
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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: 4265803Abstract: The invention entitled "Polymers containing polyalkylpiperidines and use thereof as stabilizers" provides a class of polymers in which groups containing sterically hindered polyalkylpiperidines are linked in the main chain of the polymers via bridging members containing 2-hydroxy-1,3-trimethylene groups.The polymers show superior stabilizing effects for various synthetic polymers such as polyolefins against degradation thereof induced by light and/or heat. The polymers have advantages, as compared with known stabilizer compounds, that they hardly volatile upon processing with heating or during storage of articles containing thereof, and that they are resistant to extraction with solvents from articles containing thereof.Type: GrantFiled: August 7, 1978Date of Patent: May 5, 1981Assignee: Sankyo Company LimitedInventors: Nobuo Soma, Syoji Morimura, Takao Yoshioka, Tomoyuki Kurumada
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Patent number: 4260689Abstract: Condensation polymers or addition polymers which contain sterically hindered polyalkylpiperidine groups are proposed as light stabilizers for plastics. The polymers concerned are relatively low-molecular polymers and a difunctional derivative of a polyalkylpiperidine is additionally used for the manufacture of these. The piperidine radical can be present in the main chain or as a side group of the polymeric stabilizer. Polymeric stabilizers of this type do not tend to migrate out of the plastic or to be removed by extraction; they are therefore very permanent in use.Type: GrantFiled: December 4, 1978Date of Patent: April 7, 1981Assignee: Ciba-Geigy CorporationInventors: Jean Rody, Michael Rasberger
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Patent number: 4260700Abstract: A mixture of an amine-terminated liquid polymer and a non-cycloaliphatic epoxy resin cures rapidly at ambient temperatures under water while displacing water from substrate surfaces and bonding strongly thereto. The mixture comprises (A) 1 equivalent of at least one non-cycloaliphatic epoxy resin, (B) from about 0.01 to about 1.5 equivalents of at least one amine-terminated liquid polymer having a carbon-carbon backbone, (C) optionally, a chain extender or crosslinker, (D) optionally, a curing agent, and (E) optionally, other compounding ingredients. The mixture is useful as an underwater repair putty, adhesive, coating or the like.Type: GrantFiled: January 24, 1977Date of Patent: April 7, 1981Assignee: The B.F. Goodrich CompanyInventors: Thomas R. Cassutt, James W. Messerly, Ronald L. Senderling
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Patent number: 4255311Abstract: A storage-stable, formaldehyde-free composition containing a water-soluble epoxide resin, an acrylic copolymer and an aliphatic polyamine or alkanolamine. This composition is used for the treatment of textile material containing hydroxyl groups and imparts to the fabrics a high resistance to creasing.Type: GrantFiled: November 26, 1979Date of Patent: March 10, 1981Assignee: Ciba-Geigy CorporationInventors: Sameer H. Eldin, Hanspeter Gysin
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Patent number: 4251414Abstract: A cathodic sediment type of electrodeposition paint composition which consists of an aqueous medium, a resinous binder dissolved or dispersed therein and an accelerating catalyst. The resinous binder is an acid neutralized reaction mixture of a first and a second component in a weight ratio of 99 to 20 parts of the first component to 1 to 80 parts of the second component. The first component is an addition material of a polybutadiene terminating in an epoxy group and a primary or secondary amino compound. The second component is an addition material of an epoxy resin and a primary or secondary amino compound. The accelerating catalyst is selected from the group consisting of an oleosoluble organic acid salt of a transition metal, the metal in turn being selected from the group consisting of iron, vanadium and titanium.Type: GrantFiled: June 13, 1979Date of Patent: February 17, 1981Assignee: Nippon Soda Company, Ltd.Inventors: Hisao Nakada, Michisuke Harada, Yukio Yamase, Ryuji Matsui
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Patent number: 4246145Abstract: A glass fiber sizing composition for the reinforcement of resin matrices which comprises one or more adhesive agents, non-ionic lubricants, organo-silanes, and cationic lubricants as well as a coadhesive such as gelatin, another silane or some sort of glass-resin binding agent and demineralized water as a complement. The organo-silanes are from the group comprising the organo-silanes containing an organic chain of the polyazamide type and the organo-silanes whose organic chain contains at least one phenyl radical and at least two secondary or tertiary amine groups. The addition of the organo-silanes to the sizing composition improves the tensile strength of the sized strands. These organo-silanes are good organic glass-resin binding agents and their presence decreases the risk of rupture of the strands during the winding operation.Type: GrantFiled: January 18, 1978Date of Patent: January 20, 1981Assignee: Saint-Gobain IndustriesInventors: Jacques Molinier, Jacques Mahler, Gilbert Bocquet, Bernard de Massey
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Patent number: 4246368Abstract: A powder coating composition for forming multi layer coatings comprising:(1) at least one of finely divided thermosetting addition copolymers having a glass transition temperature of 35.degree. to 75.degree. C. and comprising as comonomers a wt. % of a hardness imparting monomer and b wt. % of a softness imparting monomer based on the copolymer wherein a+b.ltoreq.60, b.ltoreq.a and b.ltoreq.20, and(2) at least one of finely divided thermosetting resinous materials having incompatibility or low compatibility with the copolymer and a substantially greater surface tension than the copolymer when melted at the same temperature and substantially differing from the copolymer in composite parameter.Type: GrantFiled: May 5, 1978Date of Patent: January 20, 1981Assignee: Kansai Paint Company, LimitedInventor: Heihachi Murase
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Patent number: 4246089Abstract: A polyamine/epoxy ether graft copolymer having an acrylic polamine backbone with secondary amine and hydroxy functionality, part of which is terminal primary hydroxy groups, onto which is grafted an epoxy ether. The ether is an epoxy resin preferably reacted with nonylphenol resulting in a monoepoxide ether with one or less epoxy group per epoxy ether molecule. The ether is reacted with part of the secondary amine on the acrylic backbone. This system can be formulated to a nearly-neutral pH cathodic dispersion with good cure response at 150.degree.-175.degree. C. using conventional aminoplast crosslinkers.Type: GrantFiled: November 30, 1979Date of Patent: January 20, 1981Assignee: E. I. Du Pont de Nemours and CompanyInventor: Isidor Hazan
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Patent number: 4242253Abstract: A powder coating composition useful for coating metal substrates to provide a low gloss finish; the powder particles are a blend of(a) a polyester or a blend of polyesters,(b) an epoxy resin,(c) triglycidyl isocyanurate,(d) calcium carbonate pigment and(e) finely divided polypropylene particles;The composition is particularly useful for providing the interior of automobiles, station wagons and trucks with a low gloss finish.Type: GrantFiled: June 4, 1979Date of Patent: December 30, 1980Assignee: E. I. Du Pont de Nemours and CompanyInventor: Michael D. Yallourakis
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Patent number: 4241682Abstract: Solutions of polyethylenimine or a hydrophilic derivative thereof and a hydrophilic acrylic polymer for coating watercraft below the waterline. The coating results in reduced drag by the water on the watercraft as it travels through the water. The coating also acts as a glaze coating which protects and increases the life of paint on the surfaces over which it is coated.Type: GrantFiled: October 7, 1974Date of Patent: December 30, 1980Assignee: Milton K. RubinInventor: Felix Konstandt
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Patent number: 4234468Abstract: The present invention relates to a special copolymer solution consisting of acrylic resin containing 70 to 90% by weight of copolymer solids and 10 to 30% by weight of solvent. The invention also relates to a process for the manufacture of the copolymers which are present in the copolymer solution; additionally, the invention relates to the use of the copolymer solution for the manufacture of coating compositions for lacquer systems of low solvent content which contain polyisocyanates and which contain the copolymer manufactured according to the invention as a resin component which carries hydroxyl groups.Type: GrantFiled: February 21, 1979Date of Patent: November 18, 1980Assignee: Hoechst AktiengesellschaftInventor: Horst Dalibor
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Patent number: 4234699Abstract: Condensation polymers or addition polymers which contain sterically hindered polyalkylpiperidine groups are proposed as light stabilizers for plastics. The polymers concerned are relatively low-molecular polymers and a difunctional derivative of a polyalkylpiperidine is additionally used for the manufacture of these. The piperidine radical can be present in the main chain or as a side group of the polymeric stabilizer. Polymeric stabilizers of this type do not tend to migrate out of the plastic or to be removed by extraction; they are therefore very permanent in use.Type: GrantFiled: November 29, 1978Date of Patent: November 18, 1980Assignee: Ciba-Geigy CorporationInventors: Jean Rody, Michael Rasberger
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Patent number: 4225480Abstract: Amine group-containing addition interpolymers having improved stability under conditions of storage and use are prepared by interpolymerizing at least one polymerizable ethylenically unsaturated carboxylic acid monomer and at least one polymerizable ethylenically unsaturated aminolysis-resistant organic monomer to form an addition interpolymer containing carboxyl groups pendent to the polymer chain and aminolysis-resistant organic groups pendent to the polymer chain, following which a portion of the pendent carboxyl groups of the addition interpolymer are reacted with an alkylenimine to form pendent amine groups and a portion of the pendent carboxyl groups of the addition interpolymer are neutralized with a basic compound to form pendent anionic salt groups. The addition interpolymer is preferably reducible with organic solvents, water or a mixture thereof, and can be utilized as pigment grinding vehicles or they can be formulated with conventional additives to form useful coating compositions.Type: GrantFiled: July 31, 1978Date of Patent: September 30, 1980Assignee: PPG Industries, Inc.Inventors: Karl F. Schimmel, Roger M. Christenson, Jerome A. Seiner, James A. Claar
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Patent number: 4218294Abstract: Release coatings are provided by including in a liquid monomer or prepolymer polymerizable by electromagnetic or ionizing radiation a waxy material of limited compatibility therein. Upon application of a film of such material by casting, coating or printing, a thin layer of the waxy material migrates to the surface to provide, after cure, the desired release properties. The thin surface layer of waxy material also tends to exclude oxygen from the film to permit radiant curing in air. Preferably the polymerizable liquid comprises acrylate monomers with or without unsaturated prepolymers co-polymerizable therewith dissolved therein. Novel prepolymers especially useful for providing release films and other radiation curable coatings are described, including the reaction product of polyamides, containing primary and secondary amine groups with unsaturated polybasic carboxylic acids and particular reaction products of polyether triols with toluene diisocyanate, modified with unsaturated monomers.Type: GrantFiled: September 21, 1977Date of Patent: August 19, 1980Assignee: Design Cote Corp.Inventor: Karl Brack
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Patent number: 4212782Abstract: Disclosed are solid, readily water-soluble addition polymers of acid addition salts of methacrylic acid and a 2-mono(lower)alkylaminoethyl methacrylate, whose lower alkyl group has up to 6 carbons and is straight or branched chain or cyclic. These polymers are insoluble in pentane, hexane and butane below their boiling points, and their aqueous solutions show amphoteric activity. These polymers result from polymerizing the starting monomeric acid addition salt of methacrylic acid and a 2-mono(lower)alkylaminoethyl methacrylate in the ratio of from about one mol to about 1.5 mols of one of them per mol of the other. Also disclosed is the method of producing these addition polymers by heating the starting acid addition salt under pressure in a low boiling aliphatic solvent at a temperature above its boiling point, from which after lowering the temperature the resulting addition polymer readily is separated as a light weight finely divided product.Type: GrantFiled: May 8, 1978Date of Patent: July 15, 1980Assignee: Normac, Inc.Inventor: Max Klein
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Patent number: 4205155Abstract: 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: GrantFiled: August 25, 1978Date of Patent: May 27, 1980Inventor: David H. Blount
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Patent number: 4187367Abstract: A process is disclosed for making a cured epoxy resin which has improved adhesion and peel strength. The cured resin is made by combining an epoxy resin with a polyether diureide having terminal ureido or monosubstituted ureido groups and having a molecular weight of from about 2000 to 3000 and an aminoalkylene derivative of a polyoxyalkylenepolyamine. The cured resin is useful, for example, for bonding metals.Type: GrantFiled: March 27, 1978Date of Patent: February 5, 1980Assignee: Texaco Development CorporationInventor: Harold G. Waddill
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Patent number: 4183869Abstract: Novel thermosetting oligomers are formed by reacting epoxy prepolymers with aminoarylacetylenes. When heated to 170.degree. C. or above, these oligomers undergo acetylenic polymerization to form resins which exhibit superior thermal and hydrolytic stability when compared to conventionally cured epoxy resins.Type: GrantFiled: August 4, 1978Date of Patent: January 15, 1980Assignee: Hughes Aircraft CompanyInventor: Norman Bilow
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Patent number: 4181645Abstract: An elastic composition curable at room temperature comprising (A) a diamine of a specified structure having a molecular weight of about 5,000 to about 25,000, (B) a diepoxy compound in an amount such that the mole ratio of the epoxy groups in the diepoxy compound to the primary amino groups in diamine (A) is from 0.5 to 5.0, and (C) a mixture of (i) a diacrylic acid ester and/or a dimethacrylic acid ester and (ii) a tri- or higher polyacrylic acid and/or a tri- or higher polymethacrylic acid ester in which 5 to 90% of the acryloyl and/or methacryloyl groups are derived from the diacrylic and/or dimethacrylic acid ester, the amount of said mixture being such that the mole ratio of the sum of the acryloyl and methacryloyl groups in the mixture to the primary amino groups in diamine (A) is from 0.1 to 2.Type: GrantFiled: October 26, 1978Date of Patent: January 1, 1980Assignee: Mitsui Petrochemical Industries, Ltd.Inventor: Tatsuo Kinoshita
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Patent number: 4179478Abstract: An improved process for the production of lacquer binders from 1,2-polyepoxides having more than one 1,2-epoxide group per molecule, comprising the steps of:(a) reacting the 1,2-polyepoxide with from 0.01 to 0.6 NH-equivalents, based on one epoxide equivalent, of an optionally substituted active amine hydrogen containing ammonium carbonic acid salt;(b) reacting the thus obtained compound with from 0.40 to 0.90 carboxyl equivalent, based on on epoxide equivalent of acrylic acid, methacrylic acid or a mixture thereof; and optionally(c) reacting the compound obtained from step (b) with from 0.40 to 0.2 carboxyl equivalents, based on one epoxide group, or a saturated aliphatic monocarboxylic acid;so that at least 80% of the epoxide groups originally present are reacted.Type: GrantFiled: June 13, 1978Date of Patent: December 18, 1979Assignee: Bayer AktiengesellschaftInventors: Hans J. Rosenkranz, Hans-Joachim Traenckner, Karl Fuhr
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Patent number: 4172062Abstract: Nongelled, amine functional polymers dispersible in water with the aid of a solubilizing acid are provided by copolymerizing (A) an ethylenically unsaturated hydroxy functional amine adduct free of epoxy groups and containing from about 1.4 to about 2.0 ethylenically unsaturated amine groups per molecule, formed from a polyepoxide having a 1,2-epoxy equivalency of from 1.4 to about 2.0 and at least a stoichiometric amount of a secondary amine with two unsaturated groups; and (B) copolymerizable monoethylenically unsaturated monomers, a portion of which is amine-functional. The water solutions are particularly useful to enable corrosion resistant coatings to be electrodeposited at the cathode.Type: GrantFiled: December 15, 1977Date of Patent: October 23, 1979Assignee: DeSoto, Inc.Inventors: Kazys Sekmakas, Raj Shah
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Patent number: 4172177Abstract: A water-insoluble hydrophilic polymer composition capable of crosslinking at ambient temperature. The composition contains (A) a water-insoluble hydrophilic copolymer prepared by copolymerizing (a) at least one carboxyl group containing ethylenically unsaturated monomer selected from acrylic acid, methacrylic acid, maleic anhydride, fumaric acid, itaconic acid and citraconic acid, (b) at least one amino group containing ethylenically unsaturated monomer of the formula: ##STR1## where R.sub.1 -R.sub.4 are specifically defined, and (c) an ethylenically unsaturated monomer selected from (i) a monomer of the formula: ##STR2## (R.sub.6 being alkyl), (II) A MONOMER OF THE FORMULA: ##STR3## and (iii) diacetone acrylamide, and (B) a polyepoxide crosslinking agent having at least two terminal epoxy groups. The water absorption rate of the polymer can be adjusted over a wide range and has sufficient coating strength and bonding strength to withstand long periods of immersion in water.Type: GrantFiled: December 13, 1977Date of Patent: October 23, 1979Assignee: Kyowa Gas Chemical Industry Co., Ltd.Inventor: Bunya Sato
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Patent number: 4165344Abstract: An epoxy resin composition comprising (a) a cyclopentadiene-type hydrocarbon resin having a hydroxyl value of 100 to 300 obtained by copolymerizing a cyclopentadiene-type monomer and a hydroxyl-containing monolefinic monomer at elevated temperatures, (b) a polyol selected from the group consisting of epoxy resins containing at least two hydroxyl groups in the molecule and epoxy resin derivatives containing at least two hydroxyl groups in the molecule and obtained by the reaction of epoxy resins with alkanolamines, and (c) an isocyanate-type curing agent. The compositions have improved low temperature curability, acid resistance and water resistance while retaining the various desirable properties of epoxy resins such as chemical resistance and oil resistance, and which when used as paints, exhibit improved adhesion to an adherend and improved re-coating adhesion to the film formed thereon.Type: GrantFiled: May 9, 1977Date of Patent: August 21, 1979Assignee: Nippon Zeon Co. Ltd.Inventors: Takao Okuda, Akira Wada
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Patent number: 4160757Abstract: An adhesive composition which shows improved stickiness and adhesive property at room temperature and exhibits an excellent adhering ability in a short time is prepared by compounding(a) an acrylonitrile-containing copolymer having carbon-to-carbon double bond(b) a phenol-polysulfide resin(c) a metal oxide, and(d) a polyfunctional electrophilic reactive compound containing at least two electrophilic reactive groups.Type: GrantFiled: February 28, 1977Date of Patent: July 10, 1979Assignee: Bridgestone Tire Co., Ltd.Inventors: Toshio Honda, Yukio Fukuura, Shoji Tanaka, Itsuo Tanuma, Yoshikatsu Suzuki, Hikaru Ishikawa
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Patent number: 4159976Abstract: A curable system such as a curable adhesive type system having a relatively long pot life is disclosed. The curable system of the present invention comprises polymer containing material including at least one curable epoxy resin, at least one imidazole type catalytic curing agent for the resin and a solvent for the epoxy resin capable of suppressing or inhibiting the catalytic reaction between the resin and curing agent at least at about room temperature, the solvent being selected from methanol, ethanol and mixtures thereof.Type: GrantFiled: March 10, 1977Date of Patent: July 3, 1979Assignee: Loctite CorporationInventor: James P. Moran, Jr.