Nitrogen Material Contains A Nitrogen Atom As Part Of A Heterocyclic Ring Patents (Class 528/94)
  • Patent number: 5155182
    Abstract: 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: Grant
    Filed: August 2, 1990
    Date of Patent: October 13, 1992
    Assignee: Schering AG
    Inventors: Christian Burba, Werner Mrotzek
  • Patent number: 5152862
    Abstract: 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: Grant
    Filed: December 17, 1990
    Date of Patent: October 6, 1992
    Assignee: Ciba-Geigy Corporation
    Inventor: Madan M. Bagga
  • Patent number: 5147905
    Abstract: 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: Grant
    Filed: May 1, 1991
    Date of Patent: September 15, 1992
    Assignee: The Dow Chemical Company
    Inventors: Robert A. Dubois, Duane S. Treybig, Allyson Malzman, Pong S. Sheih, Alan R. Whetten
  • Patent number: 5112934
    Abstract: 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: Grant
    Filed: November 27, 1989
    Date of Patent: May 12, 1992
    Assignee: The Dow Chemical Company
    Inventors: John J. Kester, H. Craig Silvis
  • Patent number: 5093458
    Abstract: 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: Grant
    Filed: December 17, 1990
    Date of Patent: March 3, 1992
    Assignee: Texaco Chemical Company
    Inventors: Harold G. Waddill, Wei-Yang Su
  • Patent number: 5087688
    Abstract: 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: Grant
    Filed: June 20, 1990
    Date of Patent: February 11, 1992
    Assignee: Ciba-Geigy Corporation
    Inventors: Urs Gruber, Friedrich Stockinger, Elvio Manso
  • Patent number: 5086155
    Abstract: 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: Grant
    Filed: September 27, 1990
    Date of Patent: February 4, 1992
    Assignee: Texaco Chemical Company
    Inventors: Harold G. Waddill, Wei-Yang Su, George P. Speranza
  • Patent number: 5086149
    Abstract: 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: Grant
    Filed: July 7, 1989
    Date of Patent: February 4, 1992
    Assignee: Hexcel Corporation
    Inventors: Kenneth S. Baron, Susan M. Brinkerhoff, Frank W. Lee, Stella M. McKinney
  • Patent number: 5081168
    Abstract: 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: Grant
    Filed: May 30, 1990
    Date of Patent: January 14, 1992
    Assignee: Shell Oil Company
    Inventors: Granville D. Edwards, Bonita S. Wilson
  • Patent number: 5081167
    Abstract: A polymaleimide/epoxy blend is cured with cyanamide to provide interlocked one-phase networks with superior thermal properties.
    Type: Grant
    Filed: July 16, 1990
    Date of Patent: January 14, 1992
    Assignee: Shell Oil Company
    Inventor: Roy J. Jackson
  • Patent number: 5080740
    Abstract: 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: Grant
    Filed: December 8, 1989
    Date of Patent: January 14, 1992
    Assignee: Schering AG
    Inventors: Christian Burba, Herbert Franz, Alwin Krotzek, Werner Mrotzek
  • Patent number: 5077376
    Abstract: 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: Grant
    Filed: May 21, 1990
    Date of Patent: December 31, 1991
    Assignee: Loctite (Ireland) Ltd.
    Inventor: John Dooley
  • Patent number: 5066735
    Abstract: 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: Grant
    Filed: April 12, 1990
    Date of Patent: November 19, 1991
    Assignee: The Dow Chemical Company
    Inventors: Louis L. Walker, Paul A. Larson
  • Patent number: 5053476
    Abstract: 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: Grant
    Filed: June 23, 1989
    Date of Patent: October 1, 1991
    Assignee: Somar Corporation
    Inventors: Ichiro Akutagawa, Kunimitsu Matsuzaki, Toshio Matsuo, Toru Shirose
  • Patent number: 5034494
    Abstract: 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: Grant
    Filed: November 16, 1989
    Date of Patent: July 23, 1991
    Assignee: Sunstar Giken Kabushiki Kaisha
    Inventors: Takao Nakajima, Masaaki Murase, Nobuo Agari
  • Patent number: 5026816
    Abstract: 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: Grant
    Filed: January 19, 1989
    Date of Patent: June 25, 1991
    Inventor: Donald J. Keehan
  • Patent number: 5021519
    Abstract: 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: Grant
    Filed: March 24, 1988
    Date of Patent: June 4, 1991
    Assignee: Aluminum Company of America
    Inventors: Uday M. Varde, Michael N. Tackie, Rakesh K. Gupta
  • Patent number: 5019639
    Abstract: 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: Grant
    Filed: April 2, 1990
    Date of Patent: May 28, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Arnold Hofer, Alex Wegmann
  • Patent number: 5006626
    Abstract: 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: Grant
    Filed: September 25, 1989
    Date of Patent: April 9, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Arnold Hofer, Hans Gempeler
  • Patent number: 5001212
    Abstract: 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: Grant
    Filed: June 27, 1989
    Date of Patent: March 19, 1991
    Assignee: SKW Trostberg Aktiengesellschaft
    Inventors: Benedikt Hammer, Bernd Graml
  • Patent number: 5001211
    Abstract: 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: Grant
    Filed: October 26, 1989
    Date of Patent: March 19, 1991
    Assignee: Texaco Chemical Company
    Inventor: Harold G. Waddill
  • Patent number: 4994536
    Abstract: 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: Grant
    Filed: June 23, 1988
    Date of Patent: February 19, 1991
    Assignee: Rhone-Poulenc Chimie
    Inventor: Rene Arpin
  • Patent number: 4973648
    Abstract: 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: Grant
    Filed: September 25, 1989
    Date of Patent: November 27, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Arnold Hofer, Hans Gempeler
  • Patent number: 4968732
    Abstract: 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: Grant
    Filed: March 23, 1990
    Date of Patent: November 6, 1990
    Assignee: Schering Aktiengesellschaft
    Inventors: Christian Burba, Werner Mrotzek
  • Patent number: 4968767
    Abstract: 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: Grant
    Filed: June 14, 1989
    Date of Patent: November 6, 1990
    Assignee: Schering AG
    Inventors: Christian Burba, Werner Mrotzek
  • Patent number: 4959439
    Abstract: 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: Grant
    Filed: February 27, 1990
    Date of Patent: September 25, 1990
    Assignee: Toyokako Kabushiki Kaisha
    Inventors: Katsumi Tanino, Morihito Nakada
  • Patent number: 4959425
    Abstract: 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: Grant
    Filed: June 27, 1989
    Date of Patent: September 25, 1990
    Assignee: The Dow Chemical Company
    Inventors: Louis L. Walker, Paul A. Larson
  • Patent number: 4948449
    Abstract: 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: Grant
    Filed: February 21, 1989
    Date of Patent: August 14, 1990
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Kent S. Tarbutton, Janis Robins, John C. Tangen
  • Patent number: 4942215
    Abstract: 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: Grant
    Filed: November 18, 1988
    Date of Patent: July 17, 1990
    Assignee: Enichem Synthesis S.p.A.
    Inventors: Alberto Greco, Luigi Raisa
  • Patent number: 4933422
    Abstract: 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: Grant
    Filed: May 15, 1989
    Date of Patent: June 12, 1990
    Assignee: SKW Trostberg Aktiengesellschaft
    Inventor: Benedikt Hammer
  • Patent number: 4931529
    Abstract: 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: Grant
    Filed: May 30, 1989
    Date of Patent: June 5, 1990
    Assignee: Schering Aktiengesellschaft
    Inventors: Christian Burba, Werner Mrotzek
  • Patent number: 4931528
    Abstract: 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: Grant
    Filed: May 8, 1989
    Date of Patent: June 5, 1990
    Assignee: Texaco Chemical Company
    Inventors: Harold G. Waddill, George P. Speranza, Wei-Yang Su
  • Patent number: 4929650
    Abstract: 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: Grant
    Filed: July 25, 1988
    Date of Patent: May 29, 1990
    Assignees: Mitsui Sekiyu Kagaku Kogyo Kabushiki Kaisha, Shinko Kosen Kogyo Kabushiki Kaisha
    Inventors: Makoto Kurauchi, Michio Hashimoto, Kiyoshi Hayasaki, Toshikazu Minami, Mutsuhiko Ohnishi, Yohei Suzuki
  • Patent number: 4925886
    Abstract: 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: Grant
    Filed: January 23, 1989
    Date of Patent: May 15, 1990
    Assignee: General Motors Corporation
    Inventors: Richard P. Atkins, Chen-Shih Wang, Thomas J. Dearlove
  • Patent number: 4925901
    Abstract: 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: Grant
    Filed: November 18, 1988
    Date of Patent: May 15, 1990
    Assignee: The Dow Chemical Company
    Inventors: James L. Bertram, Louis L. Walker, John W. Muskopf
  • Patent number: 4921928
    Abstract: 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: Grant
    Filed: June 17, 1988
    Date of Patent: May 1, 1990
    Assignee: Toyokako Kabushiki Kaisha
    Inventors: Katsumi Tanino, Morihito Kakada
  • Patent number: 4916203
    Abstract: A curable resin composition comprises an epoxy compound and a propargyl aromatic ether.
    Type: Grant
    Filed: November 14, 1988
    Date of Patent: April 10, 1990
    Assignee: Shell Oil Company
    Inventors: Anthony M. Pigneri, James Vick, III, deceased
  • Patent number: 4912190
    Abstract: 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: Grant
    Filed: May 6, 1988
    Date of Patent: March 27, 1990
    Assignee: AEG Isolier- Und Kunststoff GmbH
    Inventor: Hans-Jurgen Schafer
  • Patent number: 4906711
    Abstract: 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: Grant
    Filed: July 29, 1988
    Date of Patent: March 6, 1990
    Assignee: General Electric Company
    Inventor: Mark Markovitz
  • Patent number: 4885354
    Abstract: 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: Grant
    Filed: October 17, 1988
    Date of Patent: December 5, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Arnold Hofer, Hans Gempeler
  • Patent number: 4880892
    Abstract: 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: Grant
    Filed: August 22, 1988
    Date of Patent: November 14, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Wataru Urano, Yasuaki Sugano
  • Patent number: 4874669
    Abstract: 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: Grant
    Filed: August 15, 1988
    Date of Patent: October 17, 1989
    Assignee: The Dow Chemical Company
    Inventors: Paul A. Larson, Dale J. Aldrich, Jody R. Berman
  • Patent number: 4868059
    Abstract: 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: Grant
    Filed: November 16, 1987
    Date of Patent: September 19, 1989
    Assignee: The Dow Chemical Company
    Inventors: Louis L. Walker, Paul A. Larson
  • Patent number: 4859528
    Abstract: 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: Grant
    Filed: December 3, 1987
    Date of Patent: August 22, 1989
    Assignee: Hexcel Corporation
    Inventors: Frank W. Lee, Jon D. Neuner, Kenneth Baron
  • Patent number: 4841010
    Abstract: 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: Grant
    Filed: September 2, 1987
    Date of Patent: June 20, 1989
    Assignee: State of Israel, Ministry of Defence, Armament Development Authorithy, Rafel
    Inventor: Hanna Dodiuk
  • Patent number: 4833204
    Abstract: 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: Grant
    Filed: September 6, 1988
    Date of Patent: May 23, 1989
    Assignee: Hitachi Chemical Company, Ltd.
    Inventors: Masami Yusa, Katsuji Shibata, Yasuo Miyadera
  • Patent number: 4826991
    Abstract: 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: Grant
    Filed: February 20, 1987
    Date of Patent: May 2, 1989
    Assignee: Shikoku Chemicals Corporation
    Inventors: Natsuo Sawa, Takeshi Masuda, Takayuki Murai, Singi Okazaki, Yukio Miyauchi, Masayuki Ito
  • Patent number: 4800222
    Abstract: 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: Grant
    Filed: August 24, 1987
    Date of Patent: January 24, 1989
    Assignee: Texaco Inc.
    Inventor: Harold G. Waddill
  • Patent number: 4797455
    Abstract: 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: Grant
    Filed: August 6, 1987
    Date of Patent: January 10, 1989
    Assignee: W. R. Grace & Co.-Conn.
    Inventors: Shiow-Ching Lin, Ping-Lin Kuo
  • Patent number: 4791154
    Abstract: A composition comprising an epoxy resin and an aromatic azopolyamine curing agent is described. The use of azopolyamine curing agents in reactive monomer-diluted systems results in a high-modulus cured epoxy system.
    Type: Grant
    Filed: November 30, 1987
    Date of Patent: December 13, 1988
    Assignee: Shell Oil Company
    Inventors: Larry S. Corley, Donald R. Gehring