Nitrogen Material Contains A Nitrogen Atom As Part Of A Heterocyclic Ring Patents (Class 528/94)
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Patent number: 5155182Abstract: The invention relates to new imidazolyl derivatives, their use as curing agents in epoxy-resin compositions, and curable epoxy-resin compositions containing them and composed of an epoxy resin and compounds of the general formula ##STR1## where R is the group of the alcohol component used to produce the glycidyl ethers, R.sup.1 and R.sup.2 are, independently of each other, hydrogen, --CH.sub.3 or --C.sub.2 H.sub.5, n is 2 or 3, R.sup.3 is COOH, --CH, --COHN--N.sub.H2, --COOCH.sub.2 --CH.sub.2 --OH or COOR.sup.4, R.sup.4 being an aliphatic hydrocarbon group having from 1 to 4 carbon atoms, and m is equal to the valence of R.Type: GrantFiled: August 2, 1990Date of Patent: October 13, 1992Assignee: Schering AGInventors: Christian Burba, Werner Mrotzek
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Patent number: 5152862Abstract: Imidazoline compounds of formula ##STR1## where n denotes 2 or 3, is suitable as cure accelerator in curable epoxide resin compositions comprising a latent curing agent.Type: GrantFiled: December 17, 1990Date of Patent: October 6, 1992Assignee: Ciba-Geigy CorporationInventor: Madan M. Bagga
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Patent number: 5147905Abstract: Advanced resins and unadvanced epoxy resins are disclosed wherein the unadvanced compound and at least a portion of the advanced epoxy resin contains at least one --O--R.sup.1 --O-- or --(O--CH.sub.2 --CHR.sup.2).sub.n --O-- group as a bridge between two groups selected independently from the group consisting of (1) a saturated or unsaturated cycloaliphatic group, (2) an aromatic group, (3) a group represented by the formula ##STR1## or (4) a group represented by the formula ##STR2## Also disclosed are nucleophilic derivatives thereof, as well as curable compositions and coating compositions containing the advanced or unadvanced epoxy resins or nucleophilic modified advanced or unadvanced epoxy resins. These advanced resins and unadvanced epoxy resins provide coatings with good flexibility or formability as exhibited by good flexural or formable properties determined by reverse impact, T-bend and wedge-bend tests, chip resistance, and with good corrosion resistance and throwpower.Type: GrantFiled: May 1, 1991Date of Patent: September 15, 1992Assignee: The Dow Chemical CompanyInventors: Robert A. Dubois, Duane S. Treybig, Allyson Malzman, Pong S. Sheih, Alan R. Whetten
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Patent number: 5112934Abstract: The present invention is directed to an epoxy-containing polymeric material having nonlinear optical properties, particularly a glycidyl amine polymer, and a process for making the nonlinear optical (NLO) epoxy-containing polymeric material including poling the polymeric material under high voltage at elevated temperature for a period of time to bring about orientation of the nonlinear optical functionalities in the polymer. The polymers have enhanced thermal stability and good NLO properties.Type: GrantFiled: November 27, 1989Date of Patent: May 12, 1992Assignee: The Dow Chemical CompanyInventors: John J. Kester, H. Craig Silvis
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Patent number: 5093458Abstract: 4-Methyl-2-morpholinone is an excellent catalytic curing agent for epoxy resins. The compound is also an accelerator when combined with standard epoxy resin curing agents.Type: GrantFiled: December 17, 1990Date of Patent: March 3, 1992Assignee: Texaco Chemical CompanyInventors: Harold G. Waddill, Wei-Yang Su
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Patent number: 5087688Abstract: A fibrous composite structure impregnated with a solvent-free, curable epoxy resin matrix and comprising(a) a liquid epoxy resin or a liquid mixture of epoxy resins,(b) a liquid .beta.-hydroxyamine of formula I ##STR1## wherein X is phenyl or the radical R--O--CH.sub.2 --, wherein R is an alkyl group of 4 to 20 carbons or is phenyl or phenyl which is substituted by one or more C.sub.1 -C.sub.4 alkyl groups, a liquid mixture of .beta.-hydroxyamines of formula I or a liquid mixture of one more .beta.-hydroxyamines of formula I and of a primary monomaine different from formula I or of a primary or secondary diamine, and optionally(c) a catalytically curing tertiary amine,is virtually odourless, can be stored for several days at room temperature, and has good processing properties.Type: GrantFiled: June 20, 1990Date of Patent: February 11, 1992Assignee: Ciba-Geigy CorporationInventors: Urs Gruber, Friedrich Stockinger, Elvio Manso
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Patent number: 5086155Abstract: Disclosed is an epoxy resin curative exhibiting extended pot life, lower reactivity and lower viscosity at ambient temperatures and increased reactivity at moderately elevated temperatures which comprises from 1 to 10 parts by weight of the ortho, meta or para form of 1-isopropyl-2-tolylimidazole per 100 parts by weight epoxy resin. The latent reactive properties make the curative potentially useful in a variety of applications.Type: GrantFiled: September 27, 1990Date of Patent: February 4, 1992Assignee: Texaco Chemical CompanyInventors: Harold G. Waddill, Wei-Yang Su, George P. Speranza
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Patent number: 5086149Abstract: A fiber reinforced resin matrix composite material repair system is provided, which critically employs a resin comprising a catalyst of the formula I: ##STR1## with a multifunctional epoxy resin, the resin system being sealed in a water-proofed environment prior to being coated onto a fiber reinforcement. The coated fiber reinforcement is applied over the damaged area, the damaged portion having been removed, and the surrounding surface smoothed. An adhesive is applied to the remaining surface, prior to application of the patch. The resulting patch, which may further include thermoplastic toughening agents and an enhancer, can be directly cured at temperatures below 212.degree. F. to give physical properties similar to the original material.Type: GrantFiled: July 7, 1989Date of Patent: February 4, 1992Assignee: Hexcel CorporationInventors: Kenneth S. Baron, Susan M. Brinkerhoff, Frank W. Lee, Stella M. McKinney
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Patent number: 5081168Abstract: An epoxy resin/curing agent composition is provided comprising (i) at least one liquid epoxy resin, (ii) a reactive epoxy-functional diluent, (iii) a thixotroping atent, (iv) a polyamide resin, (v) a polyalkylenediamine, and (vi) 2-ethyl-4-methyl imidazole or derivaties thereof. The composition is suitable for use in insitu coating and rehabilitation processes and can withstand service at elevated temperatures.Type: GrantFiled: May 30, 1990Date of Patent: January 14, 1992Assignee: Shell Oil CompanyInventors: Granville D. Edwards, Bonita S. Wilson
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Patent number: 5081167Abstract: A polymaleimide/epoxy blend is cured with cyanamide to provide interlocked one-phase networks with superior thermal properties.Type: GrantFiled: July 16, 1990Date of Patent: January 14, 1992Assignee: Shell Oil CompanyInventor: Roy J. Jackson
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Patent number: 5080740Abstract: The invention relates to a process for the fabrication of fiber-reinforced wound structures, and particularly pipe fittings, by impregnation of heat-resistant fibers with binders based on epoxy resins and 3-[1-(2'-aminoethyl)-1,3-diaza-2-cyclopenten-2-yl]-heptane and/or [1-(2'-aminoethyl)-1,3-diaza-2-cyclopenten-2-yl]-2,4,4-trimethyl-1-pentane as curing agent and commonly used fillers, pigments, dyes, accelerators, curing agents, wetting and flow-control agents, and reactive diluents.Type: GrantFiled: December 8, 1989Date of Patent: January 14, 1992Assignee: Schering AGInventors: Christian Burba, Herbert Franz, Alwin Krotzek, Werner Mrotzek
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Patent number: 5077376Abstract: A latent hardener material for epoxy resins comprising a combination ofHardener (A) which is a reaction product of phthalic anhydride and diethylenetriamine, andHardener (B) which is a reaction product of a polyfunctional epoxy compound, an imidazole compound and a carboxylic acid anhydride.A combination of latent hardeners (A) and (B) can achieve cure of an epoxy resin composition in 15 minutes at 76.degree. C. A one part epoxy resin composition comprising an epoxy resin in admixture with a combination of hardeners (A) and (B) has a good shelf life.Type: GrantFiled: May 21, 1990Date of Patent: December 31, 1991Assignee: Loctite (Ireland) Ltd.Inventor: John Dooley
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Patent number: 5066735Abstract: Electrical laminates are prepared from prepreg materials prepared by impregnating a substrate with a laminating varnish comprising a solvent solution of a curable composition comprising (A) a mixture of at least one epoxy resin having an average of more than 1 but not more than 2 vicinal epoxy groups per molecule and at least one epoxy resin having an average of more than 2 vicinal epoxy groups per molecules; (B) a mixture of at least one phenolic hydroxyl-containing compound having an average of more than 1 but not more than 2 phenolic hydroxyl groups per molecule and at least one phenolic hydroxyl-containing compound having an average of more than 2 phenolic hydroxyl groups per molecule; and (C) at least one catalyst for effecting the reaction between (A) and (B).Type: GrantFiled: April 12, 1990Date of Patent: November 19, 1991Assignee: The Dow Chemical CompanyInventors: Louis L. Walker, Paul A. Larson
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Patent number: 5053476Abstract: An epoxy resin composition suitable for use as a casting resin for the potting of an ignition coil is disclosed which comprises:(A) a mixture containing(a.sub.1) a liquid, Bisphenol-type epoxy resin, and(a.sub.2) an inorganic filler,(a.sub.3) a polyether polyol; and(B) a liquid curing agent including(b.sub.1) an acid anhydride, and(b.sub.2) an imidazole compound.Type: GrantFiled: June 23, 1989Date of Patent: October 1, 1991Assignee: Somar CorporationInventors: Ichiro Akutagawa, Kunimitsu Matsuzaki, Toshio Matsuo, Toru Shirose
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Patent number: 5034494Abstract: Two part epoxy resin system comprising a main component comprising a bisphenol type epoxy resin having not more than 0.08% by weight of a content of a saponifiable chlorine-containing group and a curing component comprising a modified aromatic polyamine and a liquid imidazole, which has a long pot-life at room temperature and is curable even at an intermediate temperature such as about 50.degree. to 60.degree. C., and is useful as a paint composition, an adhesive, a lining material, a molding material and a floor covering material.Type: GrantFiled: November 16, 1989Date of Patent: July 23, 1991Assignee: Sunstar Giken Kabushiki KaishaInventors: Takao Nakajima, Masaaki Murase, Nobuo Agari
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Patent number: 5026816Abstract: The present invention relates to a novel oxirane prepolymer comprising the catalyzed reaction product of an inorganic oxide having at least one hydrolyzable oxygen with a difunctional oxirane oligomer having at least one aromatic moiety and at least one oxirane containing aliphatic moiety, characterized in that substantially all of the hydrolyzable oxygen atoms in said oxide are bonded to said oligomer and there is substantially no bonding between oligomer moieties.The present invention also relates to a novel inorganic oxide containing polymer, said polymer comprising at least three crosslinked prepolymer moieties, each said prepolymer moiety being the reaction product of an inorganic oxide having at least one hydrolyzable oxygen with a difunctional oxirane oligomer having at least one aromatic moiety and at least one oxirane containing aliphatic moiety.Type: GrantFiled: January 19, 1989Date of Patent: June 25, 1991Inventor: Donald J. Keehan
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Patent number: 5021519Abstract: A non-elastomeric epoxy having a mol wt less than about 10,000 and curing agent therefor ("epoxy-curing-agent"), both of which (epoxy/epoxy-curing-agent) are liquid while at curing temperatures, provide a continuous liquid phase in which a polyimide (PI) generally, and a bisimide (BI) in particular, may be homogeneously dispersed to form a fluidized dispersion. In one embodiment, the less viscous epoxy/epoxy-curing-agent is the dispersive medium (continuous phase) and the PI the dispersed or discontinuous phase. In the more preferred embodiment, the epoxy/epoxy-curing-agent and PI are miscible, forming a single liquid phase in which the PI is homogeneously dispersed. In each embodiment, the epoxy is essentially unreactive with the PI. Upon curing the epoxy in a first stage, to form a polymeric epoxy matrix (also referred to as "cured epoxy resin" herein) at a temperature below 150.degree. C.Type: GrantFiled: March 24, 1988Date of Patent: June 4, 1991Assignee: Aluminum Company of AmericaInventors: Uday M. Varde, Michael N. Tackie, Rakesh K. Gupta
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Patent number: 5019639Abstract: Advanced epoxy resins are disclosed which can be obtained by reacting liquid or semi-solid aromatic opoxy resins with aliphatic diols, and subsequently reacting the reaction product with mono- or binuclear bisphenols in the presence of a cyclic quaternary ammonium salt.Type: GrantFiled: April 2, 1990Date of Patent: May 28, 1991Assignee: Ciba-Geigy CorporationInventors: Arnold Hofer, Alex Wegmann
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Patent number: 5006626Abstract: An epoxy resin composition comprising an epoxy resin which is solid at room temperature and contains on average more than epoxy group per molecule, and a quaternary pyrrolidinium salt as advancement catalyst.When advanced with compounds containing two phenolic hydroxyl groups, these compositions give excellent products of low viscosity which are suitable, for example, for use in powder resin coating.Type: GrantFiled: September 25, 1989Date of Patent: April 9, 1991Assignee: Ciba-Geigy CorporationInventors: Arnold Hofer, Hans Gempeler
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Patent number: 5001212Abstract: The present invention provides an additive for heat-hardenable epoxide resin masses, wherein the additive contains or consists of adducts and/or reaction products of (a) imidazoles of the general formula: ##STR1## in which R.sub.1, R.sub.2, R.sub.3 and R.sub.4, which can be the same or different, are hydrogen atoms, alkyl, alkenyl or alkynyl radicals containing up to 3 carbon atoms or phenyl radicals, said radicals being unsubstituted or substituted, and (b) at least one aromatic hydroxy acid.The additives according to the present invention can be used alone as hardeners or, in combination with other latent hardeners, as accelerators.Type: GrantFiled: June 27, 1989Date of Patent: March 19, 1991Assignee: SKW Trostberg AktiengesellschaftInventors: Benedikt Hammer, Bernd Graml
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Patent number: 5001211Abstract: Disclosed in an epoxy resin curative exhibiting extended pot life, lower reactivity at ambient temperatures and increased reactivity at moderately elevated temperatures which comprises from 2 to 10 parts by weight of 1-isopropyl-2-methyl imidazole salicylate per 100 parts by weight epoxy resin. The latent reactive properties make the curative potentially useful in a variety of applications.Type: GrantFiled: October 26, 1989Date of Patent: March 19, 1991Assignee: Texaco Chemical CompanyInventor: Harold G. Waddill
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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: 4973648Abstract: An epoxy resin composition comprising an epoxy resin which is solid at room temperature and contains on average more than epoxy group per molecule, and a quaternary morpholinium salt as advancement catalyst.When advanced with compounds containing two phenolic hydroxyl groups, these compositions give excellent products of low viscosity which are suitable, for example, for use in powder resin coating.Type: GrantFiled: September 25, 1989Date of Patent: November 27, 1990Assignee: Ciba-Geigy CorporationInventors: Arnold Hofer, Hans Gempeler
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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: 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: 4959439Abstract: A piezoelectric polymer material comprising a cured product of a composition comprised of an epoxy resin having at least two epoxy groups in the molecules, a compound having a molecular weight not less than 1200 and containing defined numbers of amino groups, benzene rings, carbonyl groups and methylene groups, and a crosslinking agent. The cured product has dipolarly oriented micro crystals therein. A method for making such a piezoelectric polymer material is also described, in which the resin composition is thermally cured and contacted with an electric field at a high temperature to cause dipolar orientation in the product. The dipoles are frozen by cooling the product while applying the electric field.Type: GrantFiled: February 27, 1990Date of Patent: September 25, 1990Assignee: Toyokako Kabushiki KaishaInventors: Katsumi Tanino, Morihito Nakada
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Patent number: 4959425Abstract: Electrical laminates are prepared from prepreg materials prepared by impregnating a substrate with a laminating varnish comprising a solvent solution of a curable composition comprising (A) a mixture of at least one epoxy resing having an average of more than 1 but not more than 2 vicinal epoxy groups per molecule and at least one epoxy resin having an average of more than 2 vicinal epoxy groups per molecule; (B) a mixture of at least one phenolic hydroxyl-containing compound having an average of more than 1 but not more than 2 phenolic hydroxyl groups per molecule and at least one phenolic hydroxyl-containing compound having an average of more than 2 phenolic hydroxyl groups per molecule; and (C) at least one catalyst for effecting the reaction between (A) and (B).Type: GrantFiled: June 27, 1989Date of Patent: September 25, 1990Assignee: The Dow Chemical CompanyInventors: Louis L. Walker, Paul A. Larson
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Patent number: 4948449Abstract: Storage-stable, thermally-curable, one-part epoxy resin compositions comprising a curable epoxide resin; a curative amount of an aliphatic or non-aromatic cyclic polyol having about 2 to 18 carbon atoms, at least two hydroxy groups of said polyol being primary or secondary, and said polyol being free of strong acid groups, and free of electron-withdrawing substituents and large groups which cause steric hindrance in the .alpha.-position in relation to the carbon atoms attached to the methylol groups of the polyol; and a catalytic amount of an imidazole compound.Type: GrantFiled: February 21, 1989Date of Patent: August 14, 1990Assignee: Minnesota Mining and Manufacturing CompanyInventors: Kent S. Tarbutton, Janis Robins, John C. Tangen
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Patent number: 4942215Abstract: A thermosetting liquid moulding composition comprising:(a) a polyepoxide containing at least two epoxide groups per molecule;(b) a tricarboxylic acid definable by the general formula: ##STR1## where: R.sup.1, R.sup.2 and R.sup.3 have the meaning given in the description; and(c) a diacarboxylic acid anhydride.This composition can be transformed by liquid moulding into manufactured articles particularly useful in the electrical sector.Type: GrantFiled: November 18, 1988Date of Patent: July 17, 1990Assignee: Enichem Synthesis S.p.A.Inventors: Alberto Greco, Luigi Raisa
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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: 4929650Abstract: A coating material for a tendon for prestressed concrete includes a curing composition, the curing time of which is so controlled that the composition is held in an uncured fluid state for a predetermined time after the concrete hardens. After the predetermined time passes, the composition cures. By coating a tendon for prestressed concrete with the coating material having such properties, an antirust effect of the tendon, an improved adhering force of the tendon to the concrete and a decreased cost of manufacturing prestressed concrete can be obtained.Type: GrantFiled: July 25, 1988Date of Patent: May 29, 1990Assignees: Mitsui Sekiyu Kagaku Kogyo Kabushiki Kaisha, Shinko Kosen Kogyo Kabushiki KaishaInventors: Makoto Kurauchi, Michio Hashimoto, Kiyoshi Hayasaki, Toshikazu Minami, Mutsuhiko Ohnishi, Yohei Suzuki
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Patent number: 4925886Abstract: A tough, durable, high temperature epoxy tooling composition for making cast-to-size forming tools. The composition comprises a bisphenol-A epoxy, a trifunctional aromatic epoxy, an anhydride catalyst, and an imidazole catalyst. The composition may optionally contain a filler system comprising filler particles having different diameters that are interstitially-matched.Type: GrantFiled: January 23, 1989Date of Patent: May 15, 1990Assignee: General Motors CorporationInventors: Richard P. Atkins, Chen-Shih Wang, Thomas J. Dearlove
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Patent number: 4925901Abstract: Storage stable compositions are disclosed which comprise an epoxide containing compound, a phenolic hydroxyl containing compound, and a catalyst compound for catalyzing the reaction between epoxide groups and aromatic hydroxyl groups which catalyst comprises the product resulting from contacting an onium salt, amine, or amine salt with an acid or a salt of an acid having a weak nucleophilic anion.Type: GrantFiled: November 18, 1988Date of Patent: May 15, 1990Assignee: The Dow Chemical CompanyInventors: James L. Bertram, Louis L. Walker, John W. Muskopf
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Patent number: 4921928Abstract: A piezoelectric polymer material comprising a cured product of a composition comprised of an epoxy resin having at least two epoxy groups in the molecules, a compound having a molecular weight not less than 1200 and containing defined numbers of amino groups, benzene rings, carbonyl groups and methylene groups, and a crosslinking agent. The cured product has dipolarly oriented micro crystals therein. A method for making such a piezoelectric polymer material is also described, in which the resin composition is thermally cured and contacted with an electric field at a high temperature to cause dipolar orientation in the product. The dipoles are frozen by cooling the product while applying the electric field.Type: GrantFiled: June 17, 1988Date of Patent: May 1, 1990Assignee: Toyokako Kabushiki KaishaInventors: Katsumi Tanino, Morihito Kakada
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Patent number: 4916203Abstract: A curable resin composition comprises an epoxy compound and a propargyl aromatic ether.Type: GrantFiled: November 14, 1988Date of Patent: April 10, 1990Assignee: Shell Oil CompanyInventors: Anthony M. Pigneri, James Vick, III, deceased
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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: 4906711Abstract: The viscosities of solventless compositions of epoxy resins containing 1,2 epoxy groups and having at least two epoxide groups per molecule and effective amounts of hardener are markedly reduced whereby they are useful for vacuum-pressure impregnation, pre-impregnation electrical insulating material and structural composite applications by addition of a reactive diluent comprising an aromatic vinyl monomer.Type: GrantFiled: July 29, 1988Date of Patent: March 6, 1990Assignee: General Electric CompanyInventor: Mark Markovitz
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Patent number: 4885354Abstract: An epoxy resin composition comprising an epoxy resin that is liquid at room temperature and containing on average more than one epoxy group per molecule and a quarternary piperidinium salt as advancement catalyst.When advanced with compounds having two phenolic hydroxyl groups, such compositions give excellent products of low viscosity which are suitable, for example, for use in powder coating compositions.Type: GrantFiled: October 17, 1988Date of Patent: December 5, 1989Assignee: Ciba-Geigy CorporationInventors: Arnold Hofer, Hans Gempeler
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Patent number: 4880892Abstract: Advancement catalysts which are a combination of a phosphonium halide or an alkylene phosphorane and a nitrogen heterocycle selected from the group consisting of substituted or unsubstituted imidazoles, benzimidazoles, imidazolines, dihydropyrimidines, tetrahydropyrimidines, dihydroquinazolines, their salts and mixtures thereof, confer high reactivity and selectivity on epoxy resin advancement reactions. The advanced epoxy resins are useful in the preparation of coatings of high quality.Type: GrantFiled: August 22, 1988Date of Patent: November 14, 1989Assignee: Ciba-Geigy CorporationInventors: Wataru Urano, Yasuaki Sugano
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Patent number: 4874669Abstract: Electrical laminates are prepared from prepreg materials prepared by impregnating a substrate with a laminating varnish comprising a ketone solvent solution of a curable composition comprising (A) at least one aromatic based epoxy resin having an average number of epoxide groups per molecule of more than 2; (B) a mixture of (1) at least one phenolic hydroxyl-containing compound having an average of more than 1 but not more than 2 phenolic hydroxyl groups per molecule; and (2) at least one phenolic hydroxyl-containing compound having an average of more than 2 phenolic hydroxyl groups per molecule; and (C), optionally, at least one catalyst for effecting the reaction between (A) and (B).Type: GrantFiled: August 15, 1988Date of Patent: October 17, 1989Assignee: The Dow Chemical CompanyInventors: Paul A. Larson, Dale J. Aldrich, Jody R. Berman
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Patent number: 4868059Abstract: Electrical laminates are prepared from prepreg materials prepared by impregnating a substrate with a laminating varnish comprising a solvent solution of a curable composition comprising (A) a mixture of at least one epoxy resin having an average of more than 1 but not more than 2 vicinal epoxy groups per molecule and at least one epoxy resin having an average of more than 2 vicinal epoxy groups per molecule; (B) a mixture of at least one phenolic hydroxyl-containing compound having an average of more than 1 but not more than 2 phenolic hydroxyl groups per molecule and at least one phenolic hydroxyl-containing compound having an average of more than 2 phenolic hydroxyl groups per molecule; and (C) at least one catalyst for effecting the reaction between (A) and (B).Type: GrantFiled: November 16, 1987Date of Patent: September 19, 1989Assignee: The Dow Chemical CompanyInventors: Louis L. Walker, Paul A. Larson
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Patent number: 4859528Abstract: A composite tooling part having excellent dimensional stability, which may be prepared at low cost employs a one-component epoxy resin system having a catalyst which is the reaction product of an aromatic dicyanate and an imidazole. Reinforcing materials are incorporated in the matrix, and the resulting prepreg is allowed to cure at low temperature, down to about room temperature, until the free standing state is obtained. Thereafter, if elevated temperature performance is necessary, the product can be post-cured at elevated temperatures, without the need for a high temperature master.Type: GrantFiled: December 3, 1987Date of Patent: August 22, 1989Assignee: Hexcel CorporationInventors: Frank W. Lee, Jon D. Neuner, Kenneth Baron
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Patent number: 4841010Abstract: The invention relates to epoxy resins which can be cured at ambient or slightly elevated temperature. The compositions can be used as adhesives and also as structural material. The epoxy resins of the invention retain advantageous characteristics at elevated temperatures, up to about 120.degree. C. The compositions are advantageously supplied as two-pack kits which are contacted with each other when the epoxy resin is to be used. The first component is a mixture of at least two epoxides; the second component is a curing system which contains at least two amines.The components are:A. epoxies:(1) a tetraglycidyl diamino-diaromatic alkane(2) a triglycidyl ether of an amino aromatic alkaneB. amines:(1) a polyalkylene polyamine(2) an amino-terminated or carboxy terminated alkadiene rubber compound.Type: GrantFiled: September 2, 1987Date of Patent: June 20, 1989Assignee: State of Israel, Ministry of Defence, Armament Development Authorithy, RafelInventor: Hanna Dodiuk
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Patent number: 4833204Abstract: An epoxy resin composition for a copper-clad laminate comprising an epoxy resin having at least two epoxy groups in one molecule, a phenolic compound having at least two functional groups in one molecule as a hardener, an imidazole compound having a masked imino group as a hardening accelerator, and one or more of nitrogen compounds selected from the group consisting of urea derivatives represented by the formula R.sup.1 --NH--CO--NH.sub.2, wherein R.sup.1 is hydrogen or an organic group; acid amide compounds; and guanidine derivatives, which is advantageously used for the material of a copper-clad laminate. Accordingly, the copper-clad laminate is especially used for the production of printed circuit boards, and its drilling property, peeling resistance of the copper foil, adhesive property, and heat resistance are improved remarkably. In addition, this epoxy resin composition has an excellent storing stability.Type: GrantFiled: September 6, 1988Date of Patent: May 23, 1989Assignee: Hitachi Chemical Company, Ltd.Inventors: Masami Yusa, Katsuji Shibata, Yasuo Miyadera
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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: 4800222Abstract: A composition for accelerating the amine cure of epoxy resins is disclosed. The accelerating composition comprises: piperazine, tris(dimethylaminomethyl)phenol and triethanolamine.The accelerator combination is synergistic for accelerating the curing of epoxy resins in thin films or in mass. The products cured with the inventive accelerator combination demonstrated improved properties over products cured with the accelerator components individually.Type: GrantFiled: August 24, 1987Date of Patent: January 24, 1989Assignee: Texaco Inc.Inventor: Harold G. Waddill
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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: 4791154Abstract: 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: GrantFiled: November 30, 1987Date of Patent: December 13, 1988Assignee: Shell Oil CompanyInventors: Larry S. Corley, Donald R. Gehring