Five-membered Heterocyclic Ring Contains At Least One Nitrogen Atom As A Ring Member Patents (Class 528/117)
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Patent number: 4996279Abstract: Dissymmetric new epoxy polymer materials have improved processability because they can be cured at lower temperatures.Type: GrantFiled: October 7, 1988Date of Patent: February 26, 1991Assignee: Shell Oil CompanyInventor: Kenneth C. Dewhirst
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Patent number: 4996285Abstract: Novel thermosetting compositions, well adapted for the production, e.g., of molded and laminated shaped articles, are comprised of a copolymerizate of (a) at least one N,N'-bisimide, (b) at least one diprimary diamine, and (c) at least one epoxy resin.Type: GrantFiled: October 11, 1989Date of Patent: February 26, 1991Assignee: Rhone-Poulenc ChimieInventor: Rene Arpin
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Patent number: 4994536Abstract: Thermally stable bisimido polymers, devoid of diamine component and well adapted for the production of laminates, are prepared by copolymerizing (a) an N,N'-bismaleimide with (b) an acrylate comonomer, e.g., a novolak epoxy (meth)acrylate, in the presence of a catalytically effective amount of (c) an imidazole compound, and, optionally, (d) a chlorinated or brominated epoxy resin, or admixture thereof with a non-chlorinated or non-brominated epoxy resin.Type: GrantFiled: June 23, 1988Date of Patent: February 19, 1991Assignee: Rhone-Poulenc ChimieInventor: Rene Arpin
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Patent number: 4985529Abstract: The invention provides an imide compound represented by the general formula (I), ##STR1## wherein X represents a hydroxyl or amino group, Ar.sub.1 and Ar.sub.2 independently represent an aromatic residue, R.sub.1 represents a hydrogen atom or a C.sub.1 -C.sub.10 alkyl group, R.sub.2 represents a hydrogen atom, a C.sub.1 -C.sub.20 alkyl or alkoxy group or a hydroxyl group, and n represents a number of from 0 to 6, and also provides an epoxy resin composition containing the imide compound (B) and epoxy resins (A) as essential components.Type: GrantFiled: April 26, 1989Date of Patent: January 15, 1991Assignee: Sumitomo Chemical Company, Ltd.Inventors: Yasuhisa Saito, Shuichi Kanagawa, Katsuya Watanabe, Kumimasa Kamio
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Patent number: 4968732Abstract: This invention is directed to a compound of the formula ##STR1## wherein the substituents are defined hereinbelow. R is an aliphatic group, cycloaliphatic group, aryl group or araliphatic group andR.sup.1 and R.sup.2 are each independently hydrogen, lower alkyl or aryl,R.sup.3 is a chemical bond or ##STR2## Z and Z.sup.1 are independently O or NH, R.sup.5 is R,R.sup.4 is lower aliphatic, arylene, aryl lower alkylene or cycloaliphatic,wherein the aliphatic group contains up to 10 carbon atoms in the principal chain and up to a total of 15 carbon atoms;the cycloaliphatic group contains up to 10 ring carbon atoms and up to a total of 15 carbon atoms; andthe aryl group is an aromatic group containing from 6 to 10 ring carbon atoms and up to a total of 15 carbon atoms.These compounds are used as accelerators in epoxy resin compositions, comprising (a) an epoxy resin, (b) dicyandiamide and optionally (c) solvents, fillers, reinforcement materials or inert materials, pigments or aids, for the production of moldings.Type: GrantFiled: March 23, 1990Date of Patent: November 6, 1990Assignee: Schering AktiengesellschaftInventors: Christian Burba, Werner Mrotzek
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Patent number: 4968730Abstract: Preparation of pigment paste resins for cathodically depositable coating compositions based on epoxy resin-amine adducts obtained from unmodified or modified epoxy resins, which by partial or complete reaction of secondary amino groups with formaldehyde contain oxazolidine structures; whose tertiary amino groups introduced via primary-tertiary diamines are quaternized to at least 20 mol % using an organic acid and a monoglycidyl compound and which in a solution adjusted with water to a correct application viscosity contain a total of 80 to 100 millimoles of acid per 100 g of solid resin are described. The pigment pastes possess, both in concentrated and dilute form, a stability which meets practical requirements and, because of their rheology, are readily processed to ensure formation of defect-free films both during deposition and crosslinking by stoving. The applied films have good properties.Type: GrantFiled: September 21, 1989Date of Patent: November 6, 1990Assignee: Vianova Kunstharz, A.G.Inventors: Helmut Honig, Georg Pampouchidis, Herbert Matzer
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Patent number: 4968767Abstract: The invention relates to substituted 3-(N-imidazolyl)propionic hydrazides, to their use as curing agents in epoxy-resin compositions, and to curable epoxy-resin compositions containing them and comprised of (a) an epoxy resin, and (b) optionally of dicyandiamide, and (c) optionally of conventionally used nitrogen-containing heterocyclic amine compounds, for the production of molded articles.Type: GrantFiled: June 14, 1989Date of Patent: November 6, 1990Assignee: Schering AGInventors: Christian Burba, Werner Mrotzek
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Patent number: 4960860Abstract: The present invention provides an improved epoxy resin composition comprising an epoxy resin and a novel imide compound represented by the formula ##STR1## wherein X represents an --NH.sub.2 group and/or --OH group, Ar.sub.1 and Ar.sub.2 independently represent an aromatic residue, R.sub.1 represents a hydrogen atom or an alkyl group having from 1 to 10 carbon atoms, R.sub.2 represent a hydrogen atom, an alkyl or alkoxy group having from 1 to 20 carbon atoms or hydroxyl group, and each of m and n represents a number of from 0 to 30.Type: GrantFiled: May 31, 1989Date of Patent: October 2, 1990Assignee: Sumitomo Chemical Co., Ltd.Inventors: Yasuhisa Saito, Kunimasa Kamio, Mitsuhiro Shibata, Katsuya Watanabe, Yutaka Shiomi, Youichi Ueda
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Patent number: 4946911Abstract: Curable compositions comprising a curing agent and the product resulting from reacting (I) the product resulting from the free radical polymerization of (A) the composition resulting from (1) reacting (a) a compound containing an average of more than one vicinal epoxide group per molecule with (b) at least one unsaturated imide having a reactive hydrogen atom attached to the imide nitrogen atom in amounts which provide a ratio of moles of component (b) per epoxide group contained in component (a) of from about 0.01:1 to about 1.1:1; and (2) optionally, reacting the product of step (A) with (c) at least one of (i) at least one compound containing only one phenolic hydroxyl group, (ii) at least one secondary amine, or (iii) a combination of (i) and (ii) in amounts sufficient that the resulting product contains a percent epoxide value of not greater than about 1.Type: GrantFiled: May 22, 1989Date of Patent: August 7, 1990Assignee: The Dow Chemical CompanyInventor: Duane S. Treybig
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Patent number: 4939227Abstract: Novel thermoplastic polymers comprise (1) moieties of a 1,6-diaza [4.4] spirodilactam having oxyaryl-containing substituents on the spiro ring nitrogen atoms, or, optionally, moieties of a di(oxyphenyl)compound, alternating with moieties derived from a mono- or binuclear hydantoin, the differing moieties being connected by 2-hydroxy-1,3-propylene linking groups.Type: GrantFiled: May 15, 1989Date of Patent: July 3, 1990Assignee: Shell Oil CompanyInventor: Pen-Chung Wang
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Patent number: 4935478Abstract: Hot-curable compositions of matter containing (a) an unsaturated imide of the formula I ##STR1## (b) a benzaldehyde derivative of the formula II ##STR2## in which for example M=2, n=zero, o=1 R.sup.1, R.sup.2 and R.sup.3 are each hydrogen and R is 4,4'diphenylmethane are suitable for the production of mouldings having excellent thermostability and resistance to thermal ageing.Type: GrantFiled: July 29, 1988Date of Patent: June 19, 1990Assignee: Ciba-Geigy CorporationInventor: Andreas Kramer
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Patent number: 4933422Abstract: Accelerators for epoxide curing agents containing cyanamide are described which use an adduct and/or reaction product of (a) a specific imidazole derivative with (b) an organic acid having a pK.sub.A value of 0.5 to 5.0.The accelerators according to the invention impart to the epoxy resin-curing agent-accelerator system a longer shelf life compared with known accelerators.Type: GrantFiled: May 15, 1989Date of Patent: June 12, 1990Assignee: SKW Trostberg AktiengesellschaftInventor: Benedikt Hammer
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Patent number: 4931529Abstract: This invention is directed to a compound of the formula ##STR1## wherein the substituents are defined hereinbelow. These compounds are used as accelerators in epoxy resin compositions, comprising (a) an epoxy resin, (b) dicyandiamide and optionally (c) solvents, fillers, reinforcement materials or inert materials, pigments or aids, for the production of moldings.Type: GrantFiled: May 30, 1989Date of Patent: June 5, 1990Assignee: Schering AktiengesellschaftInventors: Christian Burba, Werner Mrotzek
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Patent number: 4931528Abstract: Disclosed is an epoxy resin curative exhibiting extended pot life, increased resistance to heat and chemicals, lower reactivity at ambient temperatures and increased reactivity at moderately elevated temperatures which comprises from 1 to 5 parts by weight of 1-isopropyl-2-methyl imidazole per 100 parts by weight epoxy resin. The latent reactive properties make the curative potentially useful in a variety of applications.Type: GrantFiled: May 8, 1989Date of Patent: June 5, 1990Assignee: Texaco Chemical CompanyInventors: Harold G. Waddill, George P. Speranza, Wei-Yang Su
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Patent number: 4912190Abstract: An epoxy resin composition, including epoxy resin, cyanamide as a hardener, and 2-methylimidazole or 2,4-ethyl-methylimidazole as an accelerator in hardening the epoxy resin.Type: GrantFiled: May 6, 1988Date of Patent: March 27, 1990Assignee: AEG Isolier- Und Kunststoff GmbHInventor: Hans-Jurgen Schafer
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Patent number: 4902760Abstract: A cross-linked resin produced by heating a mixture of (a) a bis(2-oxazoline) compound, (b) an aromatic polyamine compound which has at least two amino groups in the molecule and (c) a polyepoxy compound which has at least two epoxy groups in the molecule at elevated temperatures, preferably in the presence of an oxazoline ring-opening polymerization catalyst. The resin shows a high mechanical strength and toughness, a very small water absorption and a very high resistance to heat.Type: GrantFiled: October 26, 1988Date of Patent: February 20, 1990Assignee: Takeda Chemical Industries, Ltd.Inventors: Kazuhiro Arita, Yasuo Sano
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Patent number: 4889907Abstract: Novel polymeric polyhydroxy polyethers containing moieties of 2,2-di(oxyphenyl)propane and a 1,6-diazaspiro[4.4] spirodilactam having oxyaryl substituents on each spiro ring nitrogen atom, which moieties are connected by 2-hydroxy-1,3-propylidene connecting groups, are characterized by relatively high glass transition temperatures.Type: GrantFiled: September 16, 1988Date of Patent: December 26, 1989Assignee: Shell Oil CompanyInventor: Pen C. Wang
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Patent number: 4888408Abstract: Novel linear polymeric polyhydroxy polyethers characterized by alternating moieties of (1) a 1,6-diaza [4.4] spirodilactam having oxyaryl-containing substituents on each ring nitrogen atom and (2) a 2-hydroxy-1,3-propylene connecting group, exhibit relatively high glass transition temperatures.Type: GrantFiled: September 27, 1988Date of Patent: December 19, 1989Assignee: Shell Oil CompanyInventor: Pen C. Wang
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Patent number: 4871832Abstract: The invention provides an imide compound represented by the general formula (I), ##STR1## wherein X represents a hydroxyl or amino group, Ar.sub.1 and Ar.sub.2 independently represent an aromatic residue, R.sub.1 represents a hydrogen atom or a C.sub.1 -C.sub.10 alkyl group, R.sub.2 represents a hydrogen atom, a C.sub.1 -C.sub.20 alkyl or alkoxy group or a hydroxyl group, and n represents a number of from 0 to 6, and also provides an epoxy resin composition containing the imide compound (B) and epoxy resins (A) as essential components.Type: GrantFiled: January 21, 1988Date of Patent: October 3, 1989Assignee: Sumitomo Chemical Company, Ltd.Inventors: Yasuhisa Saito, Shuichi Kanagawa, Katsuya Watanabe, Kunimasa Kamio
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Patent number: 4855386Abstract: A composition is provided comprising an epoxy resin and an aromatic amine curing agent, the latter which can be described by the formula ##STR1## in which each R is selected C.sub.2 -C.sub.7 alkyl and each R' is selected from C.sub.1 -C.sub.7 alkyl. The described composition has good physical properties for high-performance composite applications and has a relatively long working life.Type: GrantFiled: December 31, 1987Date of Patent: August 8, 1989Assignee: Shell Oil CompanyInventor: Ronald S. Bauer
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Patent number: 4847348Abstract: Epoxy resins having low melt viscosities and high softening points are prepared by partially reacting the epoxy resin with a monoimide. These modified epoxy resins are useful as binders in preparing high flow-out, non-sintering powder paints, particularly in epoxy resin/polyester hybrid coatings.Type: GrantFiled: June 6, 1988Date of Patent: July 11, 1989Assignee: The Dow Chemical CompanyInventors: Gordon C. Fischer, Linda M. McKinney
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Patent number: 4826991Abstract: An imidazole compound represented by the general formula ##STR1## wherein R is an alkyl group having up to 17 carbon atoms or a phenyl group. This imidazole compound is useful as a curing agent or curing accelerator for epoxy resins.Type: GrantFiled: February 20, 1987Date of Patent: May 2, 1989Assignee: Shikoku Chemicals CorporationInventors: Natsuo Sawa, Takeshi Masuda, Takayuki Murai, Singi Okazaki, Yukio Miyauchi, Masayuki Ito
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Patent number: 4826616Abstract: A piezoelectric pressure-sensitive element comprising a dispersion of a dipolarly oriented ferroelectric ceramic powder in a cured product of a composition comprised of an epoxy resin having at least two epoxy groups in the molecules, a compound having defined numbers of amino groups, benzene rings, carbonyl groups and methylene groups, and a crosslinking agent. A methd for making such a piezoelectric pressure-sensitive element is also described, in which the resin composition comprising a ferroelectric ceramic powder is thermally cured and applied with an electric field at a high temperature to cause dipolar orientation of at least the ceramic powder.Type: GrantFiled: June 17, 1988Date of Patent: May 2, 1989Assignee: Toyokako Kabushiki KaishaInventors: Katsumi Tanino, Morihito Nakada
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Patent number: 4820797Abstract: Thermoset products are prepared by polymerizing (A) at least one thermosettable compound which contains both a maleimide group and a cyanate group such as 3-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)phenyl cyanate and optionally (B) at least one of (1) at least one aromatic polycyanate such as bisphenol A dicyanate; (2) at least one polymaleimide such as N,N'-(methylenedi-p-phenylene)bismaleimide; (3) at least one material having an average of more than one vicinal epoxide group per molecule such as a diglycidyl ether of bisphenol A; (4) at least one polymerizable ethylenically unsaturated material such as styrene; or (5) a mixture of any two or more of components 1-4 in any combination.Type: GrantFiled: May 17, 1988Date of Patent: April 11, 1989Assignee: The Dow Chemical CompanyInventor: Robert E. Hefner, Jr.
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Patent number: 4820798Abstract: Thermoset products are prepared by polymerizing (A) at least one thermosettable compound which contains both a maleimide group and a cyanate group such as 3-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)phenyl cyanate and optionally (B) at least one of (1) at least one aromatic polycyanate such as bisphenol A dicyanate; (2) at least one polymaleimide such as N,N'-(methylenedi-p-phenylene)bismaleimide; (3) at least one material having an average of more than one vicinal epoxide group per molecule such as a diglycidyl ether of bisphenol A; (4) at least one polymerizable ethylenically unsaturated material such as styrene; or (5) a mixture of any two or more of components 1-4 in any combination.Type: GrantFiled: May 17, 1988Date of Patent: April 11, 1989Assignee: The Dow Chemical CompanyInventor: Robert E. Hefner, Jr.
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Patent number: 4816531Abstract: A curable composition is provided comprising a bismaleimide resin, an epoxy resin, and a phenolic resin curing agent. The composition can also contain an accelerator for enhanced low-temperature cure. The composition is useful for high-performance applications such as electrical lamination and filament-wound parts.Type: GrantFiled: March 15, 1988Date of Patent: March 28, 1989Assignee: Shell Oil CompanyInventor: Glenda C. Young
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Patent number: 4797455Abstract: Novel curing agents for heat-curable single package epoxy resins, the agents being adducts of aminoalkyl imidazoles with isocyanates. Cures are effected on heating the epoxy resin for times as short as 5 seconds.Type: GrantFiled: August 6, 1987Date of Patent: January 10, 1989Assignee: W. R. Grace & Co.-Conn.Inventors: Shiow-Ching Lin, Ping-Lin Kuo
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Patent number: 4774282Abstract: Novel curable resin compositions are disclosed containing an aromatic cyanate ester and an allyl ether of a bisphenol as a modifier. These compositions provide improved prepregs and composites. Additional modifiers including epoxy resins and bismaleimides may be included.Type: GrantFiled: November 20, 1986Date of Patent: September 27, 1988Assignee: Amoco CorporationInventor: Shahid P. Qureshi
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Patent number: 4769402Abstract: Aqueous solutions containing an epoxy resin in which epoxy groups have been replaced with a group M.sup.+ [--CH(OH)--CH.sub.2 --X--Ar--NH--C(O)--Q--C(O)--O].sup.- in which M is an alkali metal or onium ion, Q an organic bridging group having 2-3 carbon atoms in the bridge, Ar is arylene, X is S, O, NH, N-alkyl, SO.sub.2 NH or SO.sub.2 N-allyl, and preparation thereof by reacting an N-substituted imide with an epxoy resin and reacting the adduct thus formed with a base in the presence of water.Type: GrantFiled: May 11, 1987Date of Patent: September 6, 1988Assignee: Shell Oil CompanyInventors: Willem Karzijn, Petrus G. Kooijmans
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Patent number: 4751257Abstract: A resin coating composition characterized by containing as its resin binder an epoxy resin derivative having an oxazolidine ring functional group of the formula ##STR1## where R.sub.1 is an alkylene group of 2 to 6 carbon atoms, R.sub.2 and R.sub.3 are each hydrogen or methyl, and R.sub.4 and R.sub.5 are each a residue of aldehyde or ketone.Type: GrantFiled: September 9, 1986Date of Patent: June 14, 1988Assignee: Kansai Paint Co., Ltd.Inventor: Akira Tominaga
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Patent number: 4749729Abstract: New and improved heat curable compositions are disclosed comprising epoxidic prepolymers and mono- and di-imidazole-carboxamides. The compositions are stable at room temperature, but cure readily at moderate temperatures of substantially less than about 250.degree. F., preferably at about 180.degree. F. to about 200.degree. F. and especially preferably at about 160.degree. F. to about 180.degree. F. The cured neat resins are useful as adhesives and as matrix resins in reinforced composites, with excellent physical properties.Type: GrantFiled: December 23, 1985Date of Patent: June 7, 1988Assignee: American Cyanamid CompanyInventors: Dalip K. Kohli, Martin Hauser
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Patent number: 4742148Abstract: A latent catalyst for epoxy resin systems is produced by the reaction between an aromatic dicyanate and imidazoles. The catalyst provides good curability, excellent mechanical properties, and remarkably extended shelf life. It also allows curing at room temperature.Type: GrantFiled: April 17, 1987Date of Patent: May 3, 1988Assignee: Hexcel CorporationInventors: Frank W. Lee, Kenneth S. Baron
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Patent number: 4736011Abstract: Mannich condensates prepared from an imidazole, formaldehyde and a polyalkylene polyamine are useful as curing agents for epoxy resins.Preferably, a diamine is reacted with the imidazole and formaldehyde, as illustrated by the following formula: ##STR1## wherein: R represents hydrogen or a C.sub.1 -C.sub.Type: GrantFiled: October 2, 1986Date of Patent: April 5, 1988Assignee: Texaco Inc.Inventors: Harold G. Waddill, George P. Speranza
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Patent number: 4728742Abstract: Imides of the formula I ##STR1## wherein R.sup.1, R.sub.2, R.sup.3 and n have the meanings defined in claim 1, are intermediates for producing polymers having excellent physical properties, and for producing sulfonic acid esters.Type: GrantFiled: June 19, 1985Date of Patent: March 1, 1988Assignee: Ciba-Geigy CorporationInventor: Alfred Renner
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Patent number: 4725663Abstract: N-glycidyl derivatives of certain benzo-N-heterocycles, such as 2-(3H)-benzoxazolone, may be employed as latently cross-linkable reactive diluents for epoxy resins.Type: GrantFiled: December 29, 1986Date of Patent: February 16, 1988Assignee: The Dow Chemical CompanyInventor: Theodore L. Parker
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Patent number: 4710561Abstract: A resin coating composition comprising an epoxy resin derivative having an imidazoline ring functional group of the formula ##STR1## wherein R.sub.1 represents an alkylene group having 2 to 6 carbon atoms, each of R.sub.2, R.sub.3, R.sub.4 and R.sub.5 represents a hydrogen atom or a methyl group, and R.sub.6 represents a residue of a carboxylic acid,as a resin binder. This resin coating composition is useful for cationic electrodeposition coating.Type: GrantFiled: November 26, 1986Date of Patent: December 1, 1987Assignee: Kansai Paint Co., Ltd.Inventors: Akira Tominaga, Reiziro Nishida
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Patent number: 4705833Abstract: A thermosettable heat-resistant resin composition containing (A) an amino group-terminated imide compound produced by imidating an aromatic diamine with an aromatic tetracarboxylic anhydride at a diamine:anhydride molar ratio of from 1.2:1 to 4:1, and (B) an epoxy resin having at least two epoxy groups, the molar ratio of the amino group of the imide compound to the epoxy group of the epoxy resin being 1:1.6 to 1:2.6.Type: GrantFiled: December 24, 1985Date of Patent: November 10, 1987Assignee: Sumitomo Chemical Company, LimitedInventors: Yasuhisa Saito, Hisao Takagishi, Katsuya Watanabe, Kohichi Okuno, Junichi Kenmei, Kunimasa Kamio
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Patent number: 4701512Abstract: The adducts of isocyanates wtih benzoxazolones or benzoxazinediones are novel compounds which may be employed as blocked isocyanates and are particularly useful as latent, epoxide curing agents. At typical epoxide curing temperatures, the isocyanate is oxirane or hydroxyl reactive and the benzoxazole or benzoxazinedione acts like a di- or trifunctional phenol, respectively.Type: GrantFiled: October 29, 1985Date of Patent: October 20, 1987Assignee: The Dow Chemical CompanyInventor: Theodore L. Parker
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Patent number: 4701513Abstract: This invention relates to the use of compositions of the formula: ##STR1## wherein n is 2 to 4 and X is --O--, --S-- or ##STR2## wherein R.sub.1 is an aliphatic or aromatic moiety as a curing agent for epoxy resins to form a thermoset material which has a reduced shrinkage.Type: GrantFiled: December 15, 1986Date of Patent: October 20, 1987Assignee: W. R. Grace & Co.Inventor: Shiow C. Lin
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Patent number: 4695613Abstract: Curing agents which contain carboxy groups, obtained by partial neutralization of an oligoester having an acid number in the range from 245 to 265 with a cyclic amidine, for epoxy-group-containing powder coating compositions to produce matte coatings.Type: GrantFiled: September 23, 1985Date of Patent: September 22, 1987Assignee: Huels AktiengesellschaftInventors: Juergen Olbrich, Uwe Biethan, Gernold Sorge
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Patent number: 4689388Abstract: A curable epoxy resin composition, comprising (1) an alicyclic epoxy resin having an average of more than one epoxy group per molecule, (2) a polybasic acid hydrazide, and (3) a latent curing agent for said epoxy resin which comprises an addition product obtained by reacting (a) a polyfunctional epoxy compound with (b) a compound having at least one functional group in the molecule selected from the group consisting of OH, SH, COOH and CONHNH.sub.2 together with a tertiary amino group, or by reacting said components (a) and (b) with (c) an organic compound which has more than two active hydrogen atoms in the molecule, said reactions occurring under conditions in which the ratio of (a) to (b) or (a) to (b) and (c) ranges from 0.8 to 2.5 equivalents of (a) per equivalent of the total active hydrogen atoms in component (b) and in components (b) and (c), the molar ratio of (c) to (b) being 0.2:1 to 1:1, and said addition product having a softening point of 60.degree. to 180.degree. C.Type: GrantFiled: January 23, 1986Date of Patent: August 25, 1987Assignee: Ajinomoto Co., Inc.Inventors: Kiyomiki Hirai, Koji Takeuchi, Hiroshi Sakamoto, Masahiro Abe
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Patent number: 4680378Abstract: Polymerizable compositions are disclosed which comprises a mixture of (A) at least one thermosettable compound which simultaneously contains both a maleimide group or substituted maleimide group and a cyanate group such as 3-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)phenyl cyanate and (B) at least one material containing a plurality of aromatic amine groups such as 4,4'-diaminodiphenylmethane. Also disclosed are mixtures of the above polymerizable compositions and (C) at least one other material selected from (1) aromatic polycyanates, (2) polymaleimides, (3) materials having an average of more than one vicinal epoxide group per molecule, (4) a polymerizable ethylenically unsaturated material and (5) any combination thereof. The cured, polymerized products are useful as coatings, structural or electrical laminates or composites, castings, and the like.Type: GrantFiled: October 1, 1985Date of Patent: July 14, 1987Assignee: The Dow Chemical CompanyInventor: Robert E. Hefner, Jr.
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Patent number: 4663398Abstract: Hydroxyaromatic oligomers are prepared by (I) reacting (A) an aromatic hydroxyl-containing material such as bisphenol A with (B) a cyanogen halide such as cyanogen bromide in the presence of a base such as triethylamine and (II) co-oligomerizing the cyanate-containing product from (I) with (C) a polymaleimide such as the reaction product of maleic anhydride with methylenedianiline optionally in the presence of (D) a co-oligomerization catalyst such as cobalt naphthenate. These oligomers are useful in the preparation of epoxy resins.Type: GrantFiled: February 24, 1986Date of Patent: May 5, 1987Assignee: The Dow Chemical CompanyInventor: Robert E. Hefner, Jr.
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Patent number: 4652620Abstract: The disclosure is directed to thermoset resinous compositions having utility in the area of surface coating and molding applications, the latter including the preparation of high performance composites and the use in reaction injection molding processes. The contemplated compositions are obtained by polymerizing a reaction mixture comprising a polyfunctional 2-oxazoline compound, a compound or oligomer containing a plurality of aromatic hydroxyl groups and a polyfunctional epoxide.Type: GrantFiled: October 4, 1985Date of Patent: March 24, 1987Assignee: Ashland Oil, Inc.Inventors: Timothy A. Tufts, Billy M. Culbertson
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Patent number: 4649187Abstract: Imide functional polyphenols are prepared by reacting an excess of a phenol with an unsaturated diimide which is prepared by reacting an unsaturated polycycloaliphatic dicarboxylic acid anhydride with a diamine.These materials are useful in the preparation of castings, coatings, laminates and the like.Type: GrantFiled: September 9, 1985Date of Patent: March 10, 1987Assignee: The Dow Chemical CompanyInventors: Robert E. Hefner, Jr., Mary N. White
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Patent number: 4645818Abstract: Heat-curable compositions are described, comprising(a) an epoxide resin and(b) an effective amount of a urea of formulaAr--NHCON(R.sup.3)R.sup.4whereAr represents an aromatic group linked through an aromatic carbon atom to the indicated nitrogen atom and which is substituted by an amido group, andR.sup.3 and R.sup.4 each represent an aliphatic, cycloaliphatic, or araliphatic hydrocarbyl group, optionally substituted by a halogen atom or a hydroxyl group, or R.sup.3 may further represent a hydrogen atom, or R.sup.3 nd R.sup.4, together with the indicated nitrogen atom, may represent a heterocyclic ring of 3 to 5 carbon atoms which may also have one oxygen atom in the ring.Such amidoarylureas may be used alone with the epoxide resin, or in combination with an accelerator for the heat-curing reaction, selected from dicyandiamide, carboxylic acid hydrazides, succinimide, cyanoacetamide, 1-cyano-3-(lower alkyl)guanidines, imidazoles, and carboxylic acid-tertiary amine salts.Type: GrantFiled: December 11, 1985Date of Patent: February 24, 1987Assignee: Ciba-Geigy CorporationInventor: Christopher M. Andrews
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Patent number: 4631331Abstract: 2-(3H)-benzoxazolone and certain other benzo-N-heterocycles, as such or as their adduction products with epoxides, may be employed as organo-soluble, latent phenolic curing agents for epoxy resins. The phenolic hydroxyls are provided by rearrangement of the adduction products. Excellent shelf lives, pot lives, gel times and physical properties result.Type: GrantFiled: August 9, 1985Date of Patent: December 23, 1986Assignee: The Dow Chemical CompanyInventor: Theodore L. Parker
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Patent number: 4631332Abstract: Advanced epoxides which develop desirable resin properties and processing characteristics at considerably lower degrees of advancement than conventional advancement products are obtainable by employing a benzoxazolone or a hydroxy benzimidazole as the advancing agent.Type: GrantFiled: November 8, 1985Date of Patent: December 23, 1986Assignee: The Dow Chemical CompanyInventor: Theodore L. Parker
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Patent number: 4608420Abstract: Process for the preparation of acylurethanes by reacting a urethane with compounds containing hydroxyl groups, which comprises reacting a hydroxy compound (A) with a urethane (B) in the form of an imide of the formula ##STR1## to give an acylurethane containing at least one grouping of the formula --CO--R--CO--NH--COOR.sup.1 (II). In these formulae,R denotes the hydrocarbon radical of an optionally .alpha.,.beta.-ethylenically unsaturated, aliphatic, cycloaliphatic or aromatic dicarboxylic acid or endomethylene derivatives thereof, andR.sup.1 denotes alkyl, alkoxy, alkoxyalkyl, cycloalkyl or benzyl.These acylurethanes are suitable for use as self-crosslinking curing agents or as curing agents for polyhydroxy compounds for the production of shaped articles and/or coatings.Type: GrantFiled: June 6, 1985Date of Patent: August 26, 1986Assignee: Hoechst AktiengesellschaftInventors: Gerhard Brindopke, Gerhard Johannes
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Patent number: 4608300Abstract: Fibre composite systems, in particular fibre composite laminates, can be prepared advantageously from a fibre composite impregnated with a curable epoxide resin matrix containing:(a) a liquid epoxide resin or a liquid mixture of epoxide resins,(b) an aliphatic or cycloaliphatic primary monoamine and/or disecondary diamine and(c) a tertiary amine which cures by catalysis or(d) a cycloaliphatic diamine or an aliphatic diamine or polyamine, containing not more than one sterically unhindered primary amino group,by crosslinking and curing the resin matrix below 120.degree. C.Type: GrantFiled: June 11, 1984Date of Patent: August 26, 1986Assignee: Ciba-Geigy CorporationInventor: Urs Gruber