Nitrogen Reactant Having At Least One Amino-nitrogen Atom Contains A Cycloaliphatic Ring Patents (Class 528/122)
  • Patent number: 12049539
    Abstract: The present invention relates to an epoxy resin system containing the reaction product of an epoxy resin component and an amine-based curing agent component comprising a first amine component and a second amine component, and a method for producing the epoxy resin system comprising combining an epoxy resin component with an amine-based curing agent component to form an initial epoxy resin composition, the amine-based curing agent component comprising a first amine component and a second amine component; and allowing a chemical reaction to occur between the amine-based curing agent component and the epoxy resin component to form a cured epoxy resin composition. The first amine component is N-(3-aminopropyl) cyclohexylamine and the second amine component is the hydrogenated product of oligomeric structure from the 4,4?-Methylenedianiline process.
    Type: Grant
    Filed: March 4, 2019
    Date of Patent: July 30, 2024
    Assignee: Evonik Operations GmbH
    Inventors: Pritesh G. Patel, Gamini Ananda Vedage, Peter Lucas, Joseph DiBiase
  • Patent number: 11891476
    Abstract: The present invention relates to a new structural class of phenalkamine, phenalkamine curing agent compositions, methods of making such phenalkamine, and methods of making such compositions. The phenalkamine curing agent compositions of the present invention can be prepared by reacting cardanol with an aldehyde compound and a mixture of methylene bridged poly(cycloaliphatic-aromatic)amines. These curing-agent compositions may be used to cure, harden, and/or crosslink an epoxy resin.
    Type: Grant
    Filed: October 22, 2020
    Date of Patent: February 6, 2024
    Assignee: Evonik Operations GmbH
    Inventors: Gauri Sankar Lal, Michael Cook
  • Patent number: 11377519
    Abstract: A method of increasing the glass transition point of a cured epoxy comprising a bisphenol A diglycidyl ether and a polyetheramine includes the step of including 1,8-diamino-p-menthane as an additional hardener for curing the epoxy. An epoxy formulation includes bisphenol A diglycidyl ether and a hardener including a polyetheramine and 1,8-diamino-p-menthane.
    Type: Grant
    Filed: May 7, 2019
    Date of Patent: July 5, 2022
    Assignee: Space Exploration Technologies Corp.
    Inventors: Wenhong Fan, Ryan Christopher Kennett, Joshua James Conlon
  • Patent number: 9388294
    Abstract: Provided is an epoxy-amine adduct that offers high reactivity, contributes to better adhesion between a resin and a reinforcing fiber in a fiber-reinforced composite material, and can be easily blended with another component such as a resin. The epoxy-amine adduct has two or more amino groups per molecule and is obtained by a reaction of an epoxy compound (A) having two or more alicyclic epoxy groups per molecule with an amine compound (B) having two or more amino groups per molecule.
    Type: Grant
    Filed: April 30, 2013
    Date of Patent: July 12, 2016
    Assignee: DAICEL CORPORATION
    Inventor: Masanori Sakane
  • Patent number: 9234115
    Abstract: The present disclosure relates to a water-based amine curing agent which is a reaction product obtained from the reaction of an aqueous epoxy resin dispersion and a polyamine component. The water-based amine curing agent may be used as part of a two component coating system in the curing of modified or unmodified liquid or pre-dispersed curable resin.
    Type: Grant
    Filed: June 5, 2012
    Date of Patent: January 12, 2016
    Assignee: Huntsman Advanced Materials Americas LLC
    Inventors: Hui Zhou, Derek Scott Kincaid
  • Patent number: 8980979
    Abstract: A curable composition including (a) at least one cyclic diamine, (b) at least one non-heterocyclic amine that has a pKa value of approximately 9.5 to about 12 at 25° C. for the most basic amine group in the non-heterocyclic amine molecule, (c) at least one epoxy resin, and (d) at least one alkylated phenol; (i) wherein the equivalents of the amine hydrogens from the cyclic diamine compared to the total amine hydrogens from both the cyclic diamine and the non-heterocyclic amine in the composition are greater than about 5%; (ii) wherein the ratio of the equivalents of the total amine hydrogens in the composition to the equivalents of the total epoxies in the composition is greater than or equal to about 1; and (iii) wherein the alkylated phenol is in an amount greater than about 10 wt % of the curable composition.
    Type: Grant
    Filed: February 16, 2010
    Date of Patent: March 17, 2015
    Assignee: Dow Global Technologies LLC
    Inventors: Marvin L. Dettloff, James R. Lowrey, Hemant A. Naik, Maurice J. Marks
  • Patent number: 8975312
    Abstract: Described herein is an epoxy composition comprising: a first component comprising an amine-based curing agent and a first dye, having a first color; and a second component comprising a curable epoxy resin and a second dye, having a second color. Also described herein is a shelf-life-indicating composition comprising: an amine-based curing agent; and a dye selected from (i) a cationic triarylmethane dye, wherein the cationic triarylmethane dye reversibly reacts with a primary amine; (ii) a halochromic dye having a color transition range between 7-12 when measured in an aqueous solution; or (iii) combinations thereof.
    Type: Grant
    Filed: June 29, 2011
    Date of Patent: March 10, 2015
    Assignee: 3M Innovative Properties Company
    Inventor: Adrian T. Jung
  • Patent number: 8921497
    Abstract: An adhesive for anchoring materials in or to concrete or masonry exhibits a shorter cure time than previous adhesives and comprises an epoxy compound and a curing agent of at least one aliphatic amine and at least one tertiary amine, optionally with a reactive dilent, which possesses sufficent strength to pass ICBO Heat Creep Test at 110 degrees F. and the ICBO Damp Hole Test at 75 degrees F.
    Type: Grant
    Filed: December 27, 2002
    Date of Patent: December 30, 2014
    Assignee: Illinois Tool Works Inc.
    Inventor: Jim Surjan
  • Patent number: 8865917
    Abstract: A multifunctional aromatic amine hardener composition including the reaction condensation product of (a) at least one aniline and (b) at least one non-aromatic cyclic dicarboxaldehyde; and a reactive thermosettable resin composition including (i) at least one multifunctional aromatic amine hardener composition curing agent, (ii) at least one thermoset resin, and optionally (c) at least one catalyst; and a process for preparing a thermoset product from the thermosettable composition. The hardener composition above and a thermoset resin may be used to prepare a thermoset product with improved thermo-mechanical behavior.
    Type: Grant
    Filed: May 12, 2011
    Date of Patent: October 21, 2014
    Assignee: Dow Global Technologies LLC
    Inventors: Mark B. Wilson, Stephanie L. Potisek, Ashwin Bharadwaj, Michael J. Mullins, Steven J. Guillaudeu
  • Patent number: 8828267
    Abstract: The present invention provides a composition which comprises at least one epoxy resin and a mixture comprising the 7 stereoisomers of diaminomethylcyclohexane in very specific ratios relative to one another, a process for preparing the composition, the use of the composition for producing hardened epoxides, adhesives, composite materials and moldings, a mixture comprising the 7 stereoisomers of diaminomethylcyclohexane in the specific ratios, and the use of this mixture for producing the composition.
    Type: Grant
    Filed: September 20, 2010
    Date of Patent: September 9, 2014
    Assignee: BASF SE
    Inventors: Joachim Pfeffinger, Daniela Malkowsky, Stephan Goettke
  • Patent number: 8729213
    Abstract: A curing agent composition including at least one benzylated polyamine compound. The benzylated polyamine compound is a reaction product of a benzaldehyde compound or benzyl halide compound and a polyamine according to the following formula: H2N—CH2-A-CH2-NH2 where A is a phenylene group or a cyclohexylene group. A method for making the curing agent composition and an amine-epoxy composition are also disclosed.
    Type: Grant
    Filed: September 23, 2011
    Date of Patent: May 20, 2014
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Williams Rene Edouard Raymond, Gamini Ananda Vedage
  • Patent number: 8512594
    Abstract: The present invention discloses both amine compositions and amine-epoxy compositions containing N,N?-dimethyl-meta-xylylenediamine. A novel process for producing amines such as N,N?-dimethyl-meta-xylylenediamine, and structurally similar amines, is also disclosed.
    Type: Grant
    Filed: August 25, 2008
    Date of Patent: August 20, 2013
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Frederick Herbert Walker, Robert Marjo Theodoor Rasing, Gamini Ananda Vedage, Michael Ian Cook, Peter Andrew Lucas
  • Patent number: 8466238
    Abstract: The invention aims to provide latent curing agents which exert high low-temperature curing properties when used together with ionically polymerizable compounds and which exhibit high storage stability at room temperature. Latent curing agents for ionically polymerizable compounds which agents each contain a hydroxyl-free amine imide compound having an N—N bond energy of 100 to 210 kJ/mol as determined by B3LYP functional theory method.
    Type: Grant
    Filed: December 26, 2008
    Date of Patent: June 18, 2013
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Hiroaki Tamatani, Mitsuaki Chida, Yugo Yamamoto, Yuichi Ito, Takashi Nakano, Naritoshi Yoshimura
  • Patent number: 8247517
    Abstract: The use of 1,3-substituted imidazolium salts of the formula I in which R1 and R3 independently of one another are an organic radical having 1 to 20 C atoms, R2, R4, and R5 independently of one another are an H atom or an organic radical having 1 to 20 C atoms, it also being possible for R4 and R5 together to form an aliphatic or aromatic ring, and X is a dicyanamide anion as latent catalysts for curing compositions comprising epoxy compounds.
    Type: Grant
    Filed: June 9, 2008
    Date of Patent: August 21, 2012
    Assignee: BASF SE
    Inventors: Lars Wittenbecher, Michael Henningsen, Georg Degen, Matthias Maase, Manfred Doering, Ulrich Arnold
  • Patent number: 7993751
    Abstract: The present invention provides epoxy curing agent compositions comprising alkylated aminopropylated methylene-di-(cyclohexylamine) compounds. Amine-epoxy compositions and articles produced from these amine-epoxy compositions are also disclosed.
    Type: Grant
    Filed: August 6, 2008
    Date of Patent: August 9, 2011
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Gamini Ananda Vedage, Williams Rene Raymond, Maw Lin Foo
  • Patent number: 7893136
    Abstract: A water soluble polymer comprising a copolyhydroxyaminoether having side-chains of polyalkylene oxides, an aqueous solution of said polymer and process for preparing the copolyhydroxyaminoether.
    Type: Grant
    Filed: November 25, 2009
    Date of Patent: February 22, 2011
    Assignee: Dow Global Technologies, Inc.
    Inventors: Terry W. Glass, William J. Harris, Jerry E. White, Mike Cavitt, David C. Jammer, Louis A. Willy, Jr.
  • Patent number: 7887916
    Abstract: An adhesive film comprising a cycloalkanediol modified copolymerized polyester resin film and a thermosetting vinyl ester resin composition layer which is hardened at room temperature on said polyester resin film.
    Type: Grant
    Filed: August 18, 2009
    Date of Patent: February 15, 2011
    Assignee: Mitsubishi Rayon Co., Ltd.
    Inventor: Manabu Kaneko
  • Patent number: 7598325
    Abstract: The present invention relates to a curing agent for epoxy resins comprising (A) an epoxy adduct of isophoronediamine, (B) an epoxy adduct of 1,3-bis(aminomethyl) cyclohexane, (C) isophoronediamine and (D) 1,3-bis (aminomethyl) cyclohexane wherein the weight ratio of (D) to (C) (=(D)/(C)) in said curing agent is in the range of 0.04 to 0.22, which can provide an epoxy resin composition with excellent curing performances such as curability under the condition of low temperature, excellent performances of epoxy resin cured coating films, excellent chemical resistance of epoxy resin cured coating films and excellent physical properties of epoxy resin cured products.
    Type: Grant
    Filed: January 24, 2007
    Date of Patent: October 6, 2009
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Shun Ogawa, Hisayuki Kuwahara
  • Patent number: 7468454
    Abstract: The present invention relates to a process for preparing amino-functional polyurethane prepolymers by a) preparing an NCO-functional polyurethane prepolymer by reacting an excess of one or more di- and/or polyisocyanates with at least one isocyanate-reactive compound having a functionality of at least 1.5, b) reacting the free NCO groups of the resulting polyurethane prepolymer with at least one compound containing one or more silanol groups to obtain the corresponding silylurethanes, and then c) converting the silylurethanes to amino-functional polyurethane prepolymers by hydrolysis and/or alcoholysis with decarboxylation. The present invention also relates coatings, adhesives, sealants, casting compounds or moldings obtained from these amino-functional polyurethene prepolymers.
    Type: Grant
    Filed: June 30, 2005
    Date of Patent: December 23, 2008
    Assignee: Bayer MaterialScience AG
    Inventor: Michael Mager
  • Patent number: 7414097
    Abstract: The epoxy resin curing agent of the present invention comprises a polyamino compound obtainable by addition reaction of aliphatic diamine represented by the formula (1) and styrene and a curing accelerator comprising an organic compound having at least one carboxyl group and at least one hydroxyl group within the molecule, which can achieve a low viscosity without containing environmental harmful substances such as phenol and solvents. In addition, the epoxy resin composition using said epoxy resin curing agent shows an excellent curability at low temperature and it provides a cured coating film having excellent appearance.
    Type: Grant
    Filed: March 5, 2007
    Date of Patent: August 19, 2008
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Hisayuki Kuwahara, Masatoshi Echigo, Takeshi Koyama
  • Patent number: 7396902
    Abstract: The epoxy resin curing agent of the present invention comprises a polyamino compound obtainable by addition reaction of aliphatic diamine represented by the formula (1) and styrene and a curing accelerator comprising an organic compound having at least one carboxyl group and at least one hydroxyl group within the molecule, which can achieve a low viscosity without containing environmental harmful substances such as phenol and solvents. In addition, the epoxy resin composition using said epoxy resin curing agent shows an excellent curability at low temperature and it provides a cured coating film having excellent appearance H2N—H2C-A-CH2—NH2??(1) wherein A is a phenylene group or a cyclohexylene group.
    Type: Grant
    Filed: February 9, 2004
    Date of Patent: July 8, 2008
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Hisayuki Kuwahara, Masatoshi Echigo, Takeshi Koyama
  • Patent number: 7378461
    Abstract: The invention relates to (1) a curable epoxy resin composition comprising (A) a non-gel type amine-modified epoxy resin which is obtained by reacting an epoxy resin with a polyamine and (B) at least one of boric acid and boric ester, (2) a powder form of the curable epoxy resin composition and a process for its production, and (3) a process for production of heat-resistant laminated sheets by using the curable epoxy resin composition. The invention provides (1) a curable epoxy resin composition capable of giving a cured article having a high glass transition temperature and excellent mechanical properties, (2) a powder form of curable epoxy resin composition having a high glass transition temperature, excellent mechanical properties and excellent storage stability and a process for its production, and (3) heat-resistant laminated sheets made by using the curable epoxy resin compositions and having excellent heat resistance and mechanical properties.
    Type: Grant
    Filed: October 31, 2002
    Date of Patent: May 27, 2008
    Assignee: Kawamura Institute of Chemical Research
    Inventors: Kazutoshi Haraguchi, Akira Ohbayashi
  • Patent number: 7351784
    Abstract: A chip-packaging composition includes a thermosetting resin and at least one of an N-heterocyclic carbene adduct, an imidazole, and a cycloaliphatic amine hardener. The chip-packaging composition is applied to flip-chip technology during no-flow underfill mounting of the flip-chip to a mounting substrate. The mounting substrate can be further mounted on a board. A process includes formation of the chip-packaging composition. A method includes assembly of the chip-packaging composition with the flip-chip, and further can include assembly of the mounting substrate to a board. A computing system is also included that uses the chip-packaging composition.
    Type: Grant
    Filed: September 30, 2005
    Date of Patent: April 1, 2008
    Assignee: Intel Corporation
    Inventor: Stephen E. Lehman, Jr.
  • Patent number: 7307128
    Abstract: The present invention relates to an epoxy compound, represented by a general formula (I), which is solid at ordinary temperature, has extremely low melt viscosity and has excellent curing property and which can provide a cured product which is excellent in mechanical strength, heat resistance, and moisture resistance. It also relates to a preparation method of the epoxy compound, an epoxy resin composition, and a cured product thereof. The epoxy compound is represented by the following general formula (I): (wherein R1-R10 each represent hydrogen atom or alkyl group having 1-6 carbon atoms, and n represents an integer of 0 or more).
    Type: Grant
    Filed: August 27, 2004
    Date of Patent: December 11, 2007
    Assignee: Japan Epoxy Resins Co., Ltd.
    Inventors: Atsuhito Hayakawa, Akihiro Itou
  • Patent number: 7304120
    Abstract: An epoxy compound, represented by a general formula (I) is obtained by reacting an anthrahydroquinone compound having a following general formula (II) with epihalohydrin. (wherein R1-R10 each represent hydrogen atom or alkyl group having 1-6 carbon atoms, and n represents an integer of 0 or more, and wherein A1, A2 each represent hydrogen atom or alkali metal atom, R1-R10 each represent hydrogen atom or alkyl group having 1-6 carbon atoms.
    Type: Grant
    Filed: January 26, 2007
    Date of Patent: December 4, 2007
    Assignee: Japan Epoxy Resins Co., Ltd.
    Inventors: Atsuhito Hayakawa, Akihiro Itou
  • Patent number: 6962964
    Abstract: This invention relates to improved polyepoxide resins cured with a mixture of methylene bridged poly(cycloaliphatic-aromatic)amines and a process for preparing such polyepoxide resins as well as to the methylene bridged poly(cycloaliphatic-aromatic)amine compositions and a method of making them. The improvement resides in using a curative (herein referred to as “Heavy MPCA”) comprised of the partially hydrogenated condensation product of formaldehyde and aniline or methyl substituted aniline containing a substantial amount (from 35 to 85% by weight, preferably 40 to 60% by weight) of oligomers in the form of 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14 and 15 aniline or methyl substituted aniline derivatives.
    Type: Grant
    Filed: February 6, 2003
    Date of Patent: November 8, 2005
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Michael Ulman, Gamini Ananda Vedage, David Alan Dubowik, Stephen Michael Boyce
  • Patent number: 6951907
    Abstract: A thermosetting resin is useful as an underfilling sealant form mounting semiconductors onto a printed circuit board and comprises (a) an epoxy resin containing at least one multifunctional epoxy resin, (b) an adhesion promotor having at least two secondary amine groups wherein the weight ratio of epoxy resin:adhesion promotor being from about 2:1 to about 20:1, (c) a curative of a nitrogen-containing compound and a transition metal complex; and, optionally, a polysulfide toughening agent.
    Type: Grant
    Filed: April 14, 2003
    Date of Patent: October 4, 2005
    Assignee: Henkel Corporation
    Inventor: Mark M. Konarski
  • Patent number: 6908982
    Abstract: An object of the present invention is to provide an amino composition which provides, when used as a curing agent for epoxy resin, a long pot life and an excellent appearance of a coating film to an epoxy resin composition without deteriorating the reactivity of the composition. The amino composition is obtained by addition reaction of diamine such as metaxylylenediamine and 1,3-bis(aminomethyl) cyclohexane and styrene, wherein the content of the diamine is less than 15% by weight based upon the total weight of the amino composition and the content of 1-addition product of having one phenethyl group is 50 to 100% by weight based upon the total weight of amino compound(s) obtained by the addition reaction.
    Type: Grant
    Filed: June 18, 2003
    Date of Patent: June 21, 2005
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Tetsushi Ichikawa, Hisayuki Kuwahara, Masatoshi Echigo
  • Patent number: 6838176
    Abstract: Epoxy resin compositions comprising (a) an epoxy resin, (b) a latent curing agent with curing power at 100° C. or below and (c) an aromatic amine-based curing agent and/or an alicyclic amine-based curing agent, which are curable in two stages, or epoxy resin compositions further comprising (d) a curing accelerator, as well as a prepregs comprising reinforcing fiber materials impregnated with the epoxy resin compositions. The compositions give die-releasable cured products by primary curing at low temperature, give highly heat-resistant cured products by secondary curing, and exhibit satisfactory stability at room temperature.
    Type: Grant
    Filed: April 20, 2001
    Date of Patent: January 4, 2005
    Assignee: Mitsubishi Rayon Co., Ltd.
    Inventors: Kazuya Goto, Shigetsugu Hayashi, Tadayoshi Saito, Takashi Kaneko, Kazutami Mitani, Koki Wakabayashi, Yasuo Takagi
  • Patent number: 6818318
    Abstract: Thermosetting resin compositions useful as underfill sealants for mounting semiconductor devices onto a circuit board are provided, which include epoxy resins, an adhesion promoter having at least two secondary amine groups, and a curative based on the combination of nitrogen-containing compounds and transition metal complexes.
    Type: Grant
    Filed: April 14, 2003
    Date of Patent: November 16, 2004
    Assignee: Henkel Corporation
    Inventor: Mark M. Konarski
  • Patent number: 6727325
    Abstract: The present invention has an object to provide curatives for epoxy resins and curing accelerators for epoxy resins, which both have improved subliming and decomposing properties and which, when mixed with an epoxy resin, enable the mixture to be greatly improved in thermal stability that is extremely important for the control of a curing reaction and to have a prolonged pot life (stability as a one-pack mixture comprising the epoxy resin, curative, etc.) and improved curability at low temperatures.
    Type: Grant
    Filed: June 23, 1999
    Date of Patent: April 27, 2004
    Assignee: Nippon Soda Co. Ltd.
    Inventors: Hiroshi Suzuki, Satoru Abe, Izuo Aoki
  • Patent number: 6670430
    Abstract: Thermosetting resin compositions useful as underfill sealants for mounting a semiconductor devices onto a circuit board are provided, which include epoxy resins, an adhesion promoter having at least two secondary amine groups, and a curative based on the combination of nitrogen-containing compounds and transition metal complexes.
    Type: Grant
    Filed: November 20, 2000
    Date of Patent: December 30, 2003
    Assignee: Henkel Loctite Corporation
    Inventor: Mark M. Konarski
  • Patent number: 6660386
    Abstract: A primer for flame sprayed polyolefin comprises an epoxy resin, preferably of low molecular weight and/or low viscosity; and an amine hardener, part of which becomes highly reactive on exposure to open flame, providing near instant cure of the composition under flame spray conditions. The invention is unique that it provides strong adhesion to steel, even where the surface preparation is less than ideal, as well as to concrete and other substrates. The primer eliminates the need to preheat the substrate. The primer has strong adhesion to the topcoat polyolefinic material, especially to a functionalized topcoat. The composition withstands open flame and does not char under polyolefin flame spray conditions, nor does it run or sag, and it is not prone to failure as it cools after the application of the polyolefin.
    Type: Grant
    Filed: May 21, 2001
    Date of Patent: December 9, 2003
    Assignee: Polymer Ventures, L.L.C.
    Inventor: Shah A. Haque
  • Patent number: 6617399
    Abstract: Thermosetting resin compositions useful as underfill sealants for mounting semiconductor devices onto a circuit board are provided, which include epoxy resins, an adhesion promoter having at least two secondary amine groups, a curative based on the combination of nitrogen containing compounds and transition metal complexes, and a polysulfide toughening agent.
    Type: Grant
    Filed: November 19, 2001
    Date of Patent: September 9, 2003
    Assignee: Henkel Loctite Corporation
    Inventor: Mark M. Konarski
  • Patent number: 6583528
    Abstract: A flywheel system for storing and delivering on demand electrical energy includes a flywheel supported for high speed rotation on bearings in a vacuum enclosure, and a motor-generator for spinning the flywheel up to speed and then for converting the rotational inertia in the flywheel back to electrical power. The flywheel includes a solid steel hub and a rim having only two rings press-fit on the hub with an interference fit. The rings are filament wound construction made primarily from standard modulus carbon fiber/epoxy. The steel hub stores between 40% and 60% of the energy in the flywheel. The press-fitting of the rings on the hub creates radial interference pressure between the hub and each of the composite rings that is greater than 5 ksi when at rest. The outer carbon fiber/epoxy ring is radially thinner than the inner ring, and both the hub outer diameter and the inner diameter of the assembled composite rim are tapered with the same angle.
    Type: Grant
    Filed: May 23, 2001
    Date of Patent: June 24, 2003
    Assignee: Indigo Energy, Inc.
    Inventor: Christopher W. Gabrys
  • Patent number: 6576297
    Abstract: A coating, sealant or adhesive composition curable at ambient temperatures of 40° C. or below comprises an epoxy resin and an amine-functional curing agent. The curing agent comprises a material containing at least two, and preferably at least three, heterocyclic secondary amine group.
    Type: Grant
    Filed: June 9, 2000
    Date of Patent: June 10, 2003
    Assignee: International Coatings Ltd.
    Inventors: Colin Cameron, Anna Thomas, Alastair Robert Marrion, Ian David Fletcher, Stefan Norbert Rudiger Niedoba
  • Patent number: 6562934
    Abstract: An amino compound obtained by addition reaction of diamine represented by the following formula (1) and an alkenyl compound and a process for producing the same. H2N—H2C—A—CH2—NH2  (1) wherein A is a phenylene group or a cyclohexylene group.
    Type: Grant
    Filed: September 10, 2001
    Date of Patent: May 13, 2003
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Shinichi Yonehama, Tetsushi Ichikawa
  • Patent number: 6548576
    Abstract: A one part, several-months-useful-shelf-life epoxy material suitable for potting and sealing electronic components, and which is compatible with the high, approximately 255° C. to 275° C. temperatures required for soldering modem lead-free solders comprises an intimate mixture of the following components: approximately 2 to 13 per cent by weight of diglycidyl ether bisphenol A resin; approximately 40 to 70% phenol formaldehyde resin and the following further components [(2-methylphenoxy)methyl]-oxirane or o-cresol glycidyl ether) 0.5-8% by weight; polypropyleneglycol-glycidyl ether resin (plasticizer) 2-10% by weight; cycloaliphatic polyamine (catalyst) 4-15% by weight; kaolin clay (filler) 2-20% by weight; magnesium alumino silicate (filler) 2-15% by weight; Sb2O3 (filler) 4-5% by weight, and hydrated Al2O3 (filler) 0-15% by weight.
    Type: Grant
    Filed: November 7, 2001
    Date of Patent: April 15, 2003
    Assignee: Bourns, Inc.
    Inventor: Raymond L. Winter
  • Patent number: 6476160
    Abstract: A composition comprising an epoxy resin and a ketimine compound, wherein the epoxy resin is either (1) an epoxy resin having a content of an epoxy resin having no hydroxyl group in the molecule in a range of more than 90 mol % to 100 mol % or less, (2) an epoxy resin wherein hydroxyl groups are capped with an isocyanate group-containing compound, (3) an epoxy resin wherein hydroxyl groups are capped with an alkoxysilyl group-containing compound, or (4) an epoxy resin containing an alkoxysilyl group-containing compound which is capable of capping hydroxyl groups of the epoxy resin. When either of the those epoxy resins is used and also the ketimine compound having high steric hindrance is used, a one-pack epoxy resin composition having good curing property and particularly excellent storage stability can be provided.
    Type: Grant
    Filed: July 16, 1999
    Date of Patent: November 5, 2002
    Assignee: The Yokohama Rubber Co., Ltd.
    Inventors: Hiroyuki Okuhira, Naoya Adachi
  • Patent number: 6465598
    Abstract: Amine-terminated urethane oligomer compositions are described that include very high oligomer concentrations. The compositions are melts of the amine-terminated oligomers. The compositions can include one or more property modifiers. The compositions are useful in the formation of crosslinked copolymers, especially with epoxy resins. The resulting copolymers are useful in the formation of coatings.
    Type: Grant
    Filed: February 26, 2001
    Date of Patent: October 15, 2002
    Assignee: Tennant Company
    Inventors: Joseph S. Keute, Anne-Marie Thunnissen, Robert J. Tweedy, Jr.
  • Patent number: 6451931
    Abstract: A curing agent composition for an epoxy resin which comprises (B) a reaction product obtained from (a) an amine compound represented by formula (I): wherein R1 and R2 each represent an alkyl group having 1 to 8 carbon atoms, of R1 and R2 are connected together to form an alkylene group which may contain an oxygen atom or a nitrogen atom; and n represents 1 to 6, (b) a polyamine compound comprising a dicarboxylic acid dihydrazide, (c) an organic polyisocyanate, and, optionally; (d) an epoxy compound.
    Type: Grant
    Filed: December 29, 2000
    Date of Patent: September 17, 2002
    Assignee: Asahi Denki Kogyo Kabushiki Kaisha
    Inventors: Akio Ogawa, Manabu Abe
  • Patent number: 6410127
    Abstract: An epoxy resin composition having a low viscosity around a room temperature and excellent reinforcing fiber impregnating properties provides a composite material having excellent heat resistance and mechanical properties including compressive strength. The epoxy resin composition includes an aromatic epoxy resin having at least di-functionality, an aromatic amine compound and/or an alicyclic amine compound, wherein 5 minutes after the main agent comprising the epoxy resin and the curing agent comprising the aromatic amine compound and/or the alicyclic amine compound are mixed, the composition shows a viscosity at 25° C. in the range of from 1 to 1500 mPa sec, and Tc, tc, and Tg satisfy the following equation (1): Tg≧Tc+20−k×(Tc−90)  (1), wherein k=0 when 60≦Tc<90 and k=0.35 when 90≦Tc≦200; Tc is the highest temperature (°C.
    Type: Grant
    Filed: November 8, 2001
    Date of Patent: June 25, 2002
    Assignee: Toray Industries, Inc.
    Inventors: Toshiya Kamae, Hiroki Oosedo, Shunsaku Noda, Shinji Kouchi, Ryuji Sawaoka
  • Patent number: 6399742
    Abstract: This invention concerns low viscosity aldimine and ketimine reactive diluents having multi-imine functionality, which are useful in automotive refinish coating compositions, including a process for making them and the coatings that contain them.
    Type: Grant
    Filed: June 18, 1999
    Date of Patent: June 4, 2002
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Marko Strukelj
  • Patent number: 6365708
    Abstract: This invention relates to novel polyamines which are the reaction product of A) at least one nonaromatic diamine containing from 2 to 40 carbon atoms, wherein the amine groups are primary amine groups; and B) at least one epihalohydrin of the formula  where R is hydrogen or methyl and X is chlorine or bromine; and the coatings resulting from the reaction between the above reaction product and nonaromatic epoxy resins.
    Type: Grant
    Filed: December 20, 1999
    Date of Patent: April 2, 2002
    Assignee: Cognis Corporation
    Inventors: Shailesh Shah, Anbazhagan Natesh, Joseph Mulvey, Ronald C. LaFreeda, Gaetano D. DeAngelis, Ronald T. Cash, Jr.
  • Patent number: 6346573
    Abstract: A method for the manufacture of a one-component epoxy resin system comprises mixing at 15-30° C. and reacting at room temperature over 2-14 days (A) an epoxy resin and (B) an amine solidifying system present in insufficient quantities to cause gelation to yield a product with a Kofler Heat Bank melting point of less than 55° C. and a melting point stability of at least six months at normal workshop temperatures in the presence of (C) a hardener for (A) and the reaction product of (A) and (B) which is different from (B) and remains unreacted with (A) and (B) during the their reaction, (E) an expanding agent and (D) additives other than the expanding agent, provided that the reaction between (A) and (B) does not generate enough heat to activate a reaction between the remaining epoxy groups and hardener (C) or expanding agent (E).
    Type: Grant
    Filed: May 18, 1998
    Date of Patent: February 12, 2002
    Assignee: Vantico Inc.
    Inventor: Peter Drummond Boys White
  • Patent number: 6329473
    Abstract: Epoxy resin compositions comprising polyepoxides having at least two 1,2-epoxide groups, which can be obtained by reaction of diepoxides or polyepoxides or mixtures thereof with monoepoxides, and one or more amines sterically hindered amines, such as disecondary polyoxyalkylenediamines, and/or diprimary diamines, if desired with the addition of further 1,2-epoxide compounds and also hardeners, and use thereof as a coating for crack bridging, as an adhesive and in powder surface coatings.
    Type: Grant
    Filed: March 23, 1995
    Date of Patent: December 11, 2001
    Assignee: Solutia Germany GmbH & Co., KG
    Inventors: Manfred Marten, Claus Godau
  • Patent number: 6294597
    Abstract: A curable polymeric composition which is a liquid at 20° C. and which comprises 25 to 60% by weight of a resin component which comprises an epoxy, 5 to 25% by weight of a curing agent which comprises two components, a first component which is a cycloaliphatic amine or an aromatic amine, and a second component which is a polyamide amine, and 20 to 65% by weight of an inert inorganic filler. The curable composition can be used in a method of protecting a substrate such as a pipe or a pipe joint from corrosion or mechanical damage. In the method, the curable composition is first applied to the substrate, a polymeric covering layer is applied over the curable composition with an innermost layer of a heat-activatable sealant in intimate contact with the curable composition, and the curable composition is then cured. During the curing process, the heat-activatable sealant, e.g. a hot melt adhesive, remains in contact with the curable composition and interacts therewith.
    Type: Grant
    Filed: August 4, 1997
    Date of Patent: September 25, 2001
    Inventors: James Rinde, George Pieslak, Leon C. Glover
  • Patent number: 5940570
    Abstract: A method for encapsulating segments of signal transmission devices such as splices, pressure blocks and end blocks with a room-temperature curable composition comprising:(1) a hydroxy-functional compound having a molecular weight of greater than 500 and a hydroxy functionality of 2 or more;(2) an epoxy-functional compound having an epoxy functionality of 2 or more; and(3) a curative catalyst, in an amount effective to crosslink the epoxy and hydroxy components of the respective epoxy-functional and hydroxy-functional compounds.
    Type: Grant
    Filed: August 8, 1997
    Date of Patent: August 17, 1999
    Assignee: Uniroyal Chemical Company, Inc.
    Inventors: William Davis Sigworth, Thomas Harald Peter
  • Patent number: 5789520
    Abstract: A curing agent having less odor and providing a cured resin which is excellent in appearance, mechanical properties, water resistance and chemical resistance, and a one-component type humidity-curing resin composition having excellent storage stability and providing a cured matter which is excellent in appearance and physical properties. Specifically, provided are polyaminoamide or ketimine obtained by dehydration of 2,5- and/or 2,6-bis(aminomethyl)-bicyclo?2.2.1!heptane with carboxylic acids or ketones, a curing agent for epoxy resins using the same and a one-component type humidity-curing epoxy resin or urethane prepolymer composition containing the curing agent.
    Type: Grant
    Filed: December 19, 1996
    Date of Patent: August 4, 1998
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Minato Karasawa, Takeya Abe, Takuji Shimizu, Takeshi Iwaki
  • Patent number: 5698631
    Abstract: A room-temperature curable composition useful for encapsulating transmission signal devices, comprising:(1) a hydroxy-functional compound having a molecular weight of greater than 500 and a hydroxy functionality of 2 or more;(2) an epoxy-functional compound having an epoxy functionality of 2 or more; and(3) a curative catalyst, in an amount effective to crosslink the epoxy and hydroxy components of the respective epoxy-functional and hydroxy-functional compounds. The composition is useful for encapsulating segments of signal transmission devices such as splices, pressure blocks and end blocks.
    Type: Grant
    Filed: May 30, 1996
    Date of Patent: December 16, 1997
    Assignee: Uniroyal Chemical Company, Inc.
    Inventors: William Davis Sigworth, Thomas Harald Peter