Nitrogen Reactant Contains At Least One Amino-nitrogen Atom Patents (Class 528/121)
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Patent number: 11760832Abstract: A polymer includes the reaction product of A, B, and C, and optionally D, wherein: A is a polyepoxide that is: the condensation product of phenol, formaldehyde, and epichlorohydrin; the condensation product of bisphenol A, formaldehyde, and epichlorohydrin; or a combination of said condensation products; B is at least one polyoxyalkylene with a terminal primary amine group wherein each polyoxyalkylene comprises an ethyleneoxy moiety and a propyleneoxy moiety and independently has the following structure: wherein R is a hydrogen atom or a C1-C4 group, and wherein each of x and y is independently from 0 to about 500 and x+y>0; and C is an anchoring compound that is: a secondary amine; a monocarboxylic acid; a cyclic imide; or a combination thereof, and D is an alkylating agent. This polymer is included in a composition that further includes a compound such as a particulate solid.Type: GrantFiled: February 23, 2021Date of Patent: September 19, 2023Assignee: AXALTA COATING SYSTEMS IP CO., LLCInventor: Sheau-hwa Ma
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Patent number: 11530288Abstract: The present invention generally relates to covalent network polymers prepared from an imine-linked oligomer and an independent crosslinker comprising reactive moieties selected from the group consisting of epoxy, isocyanate, bismaleimide, sulfide, polyurethane, anhydride, polyester and combinations thereof. The covalent network polymers disclosed herein are advantageously made by anhydrous reactions, which enables the highest known glass transition temperatures to date for this class of materials. Further, the disclosed covalent network polymers can be formed in continuous processes, such as additive manufacturing processes that produce three-dimensional objects or roll-to-roll processes that produce covalent network polymer films or fully cured prepreg in various size formats.Type: GrantFiled: September 6, 2019Date of Patent: December 20, 2022Assignee: MallindaInventors: Philip Taynton, Yingdong Luo, Heather Rubin, Denis Kissounko, Samuel Loob, Sarah Sadowski
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Patent number: 11279796Abstract: A heat-curing epoxy resin compositions which can in particular be used as bodyshell adhesives for motor vehicle construction. The heat-curing epoxy resin compositions contain a curing agent which can be activated through elevated temperature and has a first component K1 containing at least one epoxy resin and a second component K2 containing at least one tertiary amine and also a primary amine. These compositions, after short-term heating of 30 to 120 seconds at a temperature of 90° C. to 130° C., exhibit sufficient strength and adhesion to withstand transport-induced mechanical strains.Type: GrantFiled: May 29, 2018Date of Patent: March 22, 2022Assignee: SIKA TECHNOLOGY AGInventors: Antonio Voci, Michael Gutgsell, Christian Eyholzer
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Patent number: 10381129Abstract: Epoxy resin composition comprising a) the reaction product formed from a1) one or more epoxy compounds having at least two epoxy groups, and a2) 0.2 to 0.9 mol of acrylic acid or methacrylic acid or mixtures thereof per mole of epoxy groups, as component A; b) a solvent comprising vinyl groups as component B.Type: GrantFiled: December 12, 2011Date of Patent: August 13, 2019Assignee: ELANTAS GMBHInventors: Horst Sulzbach, Meiyong Zhou, Wan Li Chen
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Patent number: 8980979Abstract: 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: GrantFiled: February 16, 2010Date of Patent: March 17, 2015Assignee: Dow Global Technologies LLCInventors: Marvin L. Dettloff, James R. Lowrey, Hemant A. Naik, Maurice J. Marks
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Patent number: 8975312Abstract: 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: GrantFiled: June 29, 2011Date of Patent: March 10, 2015Assignee: 3M Innovative Properties CompanyInventor: Adrian T. Jung
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Patent number: 8937145Abstract: An epoxy resin composition prepared from a dihydroxydiphenyl-cycloalkane compound to form a diglycidyl ether of dihydroxydiphenyl cycloalkane compound which may be useful for making various products including, for example, powder coatings, composites and electrical laminates.Type: GrantFiled: November 10, 2010Date of Patent: January 20, 2015Assignee: Dow Global Technologies LLCInventors: Robert E. Hefner, Jr., Michael J. Mullins, Guillaume Metral, Johann-Wilhelm Frey, Bernd Hoevel
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Patent number: 8927677Abstract: A curable epoxy resin composition comprising (a) at least one epoxy resin; (b) at least one curing agent; and (c) at least one high molecular weight poly(propylene oxide) poiyol toughening agent; and a process for preparing the curable epoxy resin composition.Type: GrantFiled: March 22, 2011Date of Patent: January 6, 2015Assignee: Dow Global Technologies LLCInventors: Radhakrishnan Karunakaran, Rajesh Turakhia
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Patent number: 8921497Abstract: 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: GrantFiled: December 27, 2002Date of Patent: December 30, 2014Assignee: Illinois Tool Works Inc.Inventor: Jim Surjan
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Patent number: 8877837Abstract: A process for curing epoxy resins which comprises curing epoxy resin compositions comprising a) epoxy resins and b) a compound of the general formula I in which R1 and R2 independently of one another are hydrogen, C1-C6-alkyl, C1-C4-alkoxy-C1-C4-alkyl, C5-C6-cycloalkyl, phenyl, phenyl-C1-C4-alkyl, C2-C6-alkenyl or C2-C6-alkynyl, or R1 and R2 together are a C3-C11-alkylene group; R3 and R4 independently of one another are hydrogen, C1-C6-alkyl, C1-C4-alkoxy-C1-C4-alkyl, C5-C6-cycloalkyl, phenyl, phenyl-C1-C4-alkyl, C2-C6-alkenyl or C2-C6-alkynyl, or R3 and R4 together are a C4-C6-alkylene group; by adding amino hardeners, and the curing takes place in the presence of a compound of the following formula II in which at least one of the radicals R11, R12 and R13 is a hydrocarbon group having 1 to 10 C atoms, which is substituted with a hydroxyl group and optionally remaining radicals R11 to R13 are an unsubstituted hydrocarbon group having 1 to 10 C atoms.Type: GrantFiled: September 12, 2012Date of Patent: November 4, 2014Assignee: BASF SEInventors: Miran Yu, Rainer Klopsch
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Patent number: 8865801Abstract: The present invention relates to epoxy resin coating composition which comprises, at least, epoxy resin, a thiol-type curing agent and a curing assistant, being composed of two liquids of liquid (A) containing epoxy resin and a thiol-type curing agent and liquid (B) containing a curing assistant, which liquids are mixed just before using, wherein the thiol-type curing agent contains a branched compound containing a thiol group (P), which compound is an ester of polyhydric alcohol with thiol group-containing carboxylic acid represented by formula (1) HOCO(CH2)nCR1R2SH??(1) (in the formula, R1 represents a hydrogen atom or a linear or branched alkyl group having 1 to 10 carbon atoms, R2 represents a linear or branched alkyl group having 1 to 10 carbon atoms, and n represents an integer of 1 to 4), which exhibits a suitable pot life, excellent curability particularly at low and ordinary temperature and low toxicity.Type: GrantFiled: May 27, 2010Date of Patent: October 21, 2014Assignee: Showa Denko K.K.Inventors: Isao Yamagami, Hiroki Takenaka, Katsumi Murofushi
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Publication number: 20140256856Abstract: A liquid epoxy resin composition having a reduced tendency to crystallize including at least one liquid epoxy resin having the following generic chemical Structure (I): where n is 0 or an integer of 1 or more; and wherein n=0 is in the range of between about 1 wt % and about 90 wt %; wherein; n=1 is in the range of between about 7 wt % and about 20 wt %; n=2 is in the range of between about 0.8 wt % and about 3 wt %; and n=3 and above is in the range of about 0 wt % and about 2 wt %.Type: ApplicationFiled: November 1, 2011Publication date: September 11, 2014Applicant: Dow Global Technologies LLCInventors: Rajesh H. Turakhia, Cui-ping Chen, Bill Z. Dellinger, Ludovic Valette, Itaru Kudose, Ha Q. Pham
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Patent number: 8633293Abstract: A polymer includes a reaction product of an epoxy resin, a first crosslinking agent, and a second crosslinking agent. The first crosslinking agent is reactive with the epoxy resin and has a first molecular weight. The second crosslinking agent is reactive with the epoxy resin and has a second molecular weight of at least 2.5 times greater than the first molecular weight. The polymer has a first phase having a first glass transition temperature at which the polymer is transformable between a first shape and a second shape. The second crosslinking agent is crystallizable within the polymer and thereby has a melting temperature that is detectable within the polymer.Type: GrantFiled: November 30, 2010Date of Patent: January 21, 2014Assignee: GM Global Technology Operations LLCInventor: Ingrid A. Rousseau
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Patent number: 8586653Abstract: A process for curing an epoxy resin composition containing an epoxy resin and a compound of the general formula I: where R1 and R2 independently are hydrogen, C1-C6-alkyl, C1-C4-alkoxy-C1-C4-alkyl, C5-C6-cycloalkyl, phenyl, phenyl-C1-C4-alkyl, C2-C6-alkenyl or C2-C6-alkynyl, or R1 and R2 together are a C3-C11-alkylene group; and where R3 and R4 independently are hydrogen, C1-C6-alkyl, C1-C4-alkoxy-C1-C4-alkyl, C5-C6-cycloalkyl, phenyl, phenyl-C1-C4-alkyl, C2-C6-alkenyl or C2-C6-alkynyl, or R3 and R4 together are a C4-C6-alkylene group. The process includes adding amino hardeners, where 0.1% to 50% by weight of the amino hardeners are aliphatic, cycloaliphatic or aromatic amine compounds having 1 to 4 primary amino groups and optionally further functional groups, selected from secondary amino groups, tertiary amino groups, and hydroxyl groups.Type: GrantFiled: September 13, 2012Date of Patent: November 19, 2013Assignee: BASF SEInventors: Rainer Klopsch, Miran Yu
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Patent number: 8530604Abstract: A polymer includes a reaction product of an epoxy resin, a first crosslinking agent, and a second crosslinking agent. The first crosslinking agent is reactive with the epoxy resin and has a first molecular weight. The second crosslinking agent is reactive with the epoxy resin and has a second molecular weight of at least ten times greater than the first molecular weight. The polymer has a first phase having a first glass transition temperature and a second phase having a second glass transition temperature that is lower than the first glass transition temperature. The polymer is transformable between a first shape and a second shape at the first glass transition temperature.Type: GrantFiled: November 30, 2010Date of Patent: September 10, 2013Assignee: GM Global Technology Operations LLCInventor: Ingrid A. Rousseau
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Patent number: 8524807Abstract: Compounds VB of the formula (I) or (II), said compounds being particularly suitable as curing agents for epoxide resins. The compounds can be produced easily and rapidly. They can be used in the form of aqueous curing agents and form stabile aqueous emulsions in particular. This facilitates the formulation of ECC compounds for use primarily as coatings.Type: GrantFiled: June 12, 2009Date of Patent: September 3, 2013Assignee: Sika Technology AGInventor: Pierre-André Bütikofer
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Patent number: 8466238Abstract: 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: GrantFiled: December 26, 2008Date of Patent: June 18, 2013Assignee: Mitsui Chemicals, Inc.Inventors: Hiroaki Tamatani, Mitsuaki Chida, Yugo Yamamoto, Yuichi Ito, Takashi Nakano, Naritoshi Yoshimura
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Patent number: 8247517Abstract: 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: GrantFiled: June 9, 2008Date of Patent: August 21, 2012Assignee: BASF SEInventors: Lars Wittenbecher, Michael Henningsen, Georg Degen, Matthias Maase, Manfred Doering, Ulrich Arnold
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Patent number: 8236195Abstract: A fluorine-containing curable composition containing (A) A fluorine-containing amino compound having primary or secondary amino groups at both ends, said compound being represented by the formula (1): Y-Q-Rf—(X—Rf)n-Q-Y??(1) wherein Rf is a divalent perfluorooxyalkylene group, each Q is independently a divalent organic group having 1 to 20 carbon atoms and, optionally, containing an oxygen atom and/or a nitrogen atom, X is a divalent organic group having 1 to 20 carbon atoms and, optionally, containing an oxygen atom and/or a nitrogen atom, Y is an organic group having a primary or secondary amino group and 1 to 20 carbon atoms and, optionally, containing an oxygen atom, and n is an integer of from 1 to 20, (B) An epoxy compound having at least two epoxy groups in a molecule, in an amount such that the amount of the epoxy groups is 0.Type: GrantFiled: January 9, 2009Date of Patent: August 7, 2012Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Yasunori Sakano, Noriyuki Koike
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Patent number: 8114519Abstract: Derivatized solid epoxy resins of the formula (I), which are outstandingly suitable as impact modifiers; and compositions which include such derivatized solid epoxy resins and are outstandingly suitable as one-component heat-curable adhesives, and as structural foams which have a high impact resistance and high mechanical stability.Type: GrantFiled: October 24, 2007Date of Patent: February 14, 2012Assignee: Sika Technology AGInventors: Andreas Kramer, Juergen Finter
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Patent number: 8043460Abstract: One embodiment of the invention includes product comprising an elastomeric epoxy dry adhesive with a pull-off strength of 1-200 N/cm2 from a substrate and reversibly detached with a peel-off force less than 1 N/cm.Type: GrantFiled: October 4, 2007Date of Patent: October 25, 2011Assignee: GM Global Technology Operations LLCInventors: Tao Xie, Xingcheng Xiao
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Patent number: 8030431Abstract: A curable mixture which includes at least (a) 10 to 100 percent by weight, in relation to the sum of the components (a) and (b), of at least one bi- or polyfunctional aromatic cyanate or a prepolymer formed from at least one bi- or polyfunctional aromatic cyanate or a mixture formed from the abovementioned cyanates and/or prepolymers; (b) 0 to 90 percent by weight, in relation to the sum of the components (a) and (b), of at least one mono-, bi- or polyfunctional epoxy resin; (c) 0.5 to 30 percent by weight, in relation to the sum of the components (a) and (b), of at least one mono-, bi- or polyfunctional aromatic amine; and (d) 0 to 5 percent by weight, in relation to the sum of the components (a) and (b), of at least one catalyst from the group consisting of transition metal compounds and boron trihalides.Type: GrantFiled: October 18, 2002Date of Patent: October 4, 2011Assignee: Lonza AGInventors: Ulrich Daum, Alessandro Falchetto, Sajal Das
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Patent number: 8012292Abstract: One embodiment of the invention includes a multilayer dry adhesive system capable of reversible joining of rigid substrates.Type: GrantFiled: October 4, 2007Date of Patent: September 6, 2011Assignee: GM Global Technology Operations LLCInventors: Tao Xie, Xingcheng Xiao, Ruomiao Wang, Hamid G. Kia, Jessica A. Schroeder, Todd E. Durocher
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Patent number: 7993751Abstract: 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: GrantFiled: August 6, 2008Date of Patent: August 9, 2011Assignee: Air Products and Chemicals, Inc.Inventors: Gamini Ananda Vedage, Williams Rene Raymond, Maw Lin Foo
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Patent number: 7976665Abstract: One embodiment of the invention includes a method of joining two substrates with multilayer thermo-reversible dry adhesives and separating the two bonded substrates by completely thermally reversing the adhesion via heating.Type: GrantFiled: October 4, 2007Date of Patent: July 12, 2011Assignee: GM Global Technology Operations LLCInventors: Tao Xie, Xingcheng Xiao, Ruomiao Wang
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Patent number: 7893136Abstract: 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: GrantFiled: November 25, 2009Date of Patent: February 22, 2011Assignee: Dow Global Technologies, Inc.Inventors: Terry W. Glass, William J. Harris, Jerry E. White, Mike Cavitt, David C. Jammer, Louis A. Willy, Jr.
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Patent number: 7820772Abstract: An amine hardener for epoxy resins which comprises an amine adduct (A) and a low-molecular amine compound (B) as major components, wherein the molecular weight distribution of the amine adduct (A), which is defined by the ratio of the weight-average molecular weight to the number-average molecular weight, is 3 or lower and the low-molecular amine compound (B) is contained in an amount of 0.001 to 1 part by mass per 100 parts by mass of the amine adduct (A).Type: GrantFiled: March 30, 2005Date of Patent: October 26, 2010Assignee: Asahi Kasei Chemicals CorporationInventors: Taketoshi Usui, Kazuhiko Yamamoto, Hisanao Yamamoto, Kazuhiro Daikai
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Patent number: 7678872Abstract: 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: GrantFiled: July 1, 2008Date of Patent: March 16, 2010Assignee: Dow Global Technologies, Inc.Inventors: Terry W. Glass, William J. Harris, Jerry E. White, Mike Cavitt, David C. Jammer, Louis A. Willy, Jr.
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Patent number: 7504438Abstract: The invention comprises a polymeric demulsifier, methods of producing the demulsifier and methods of using the demulsifier. The demulsifier is the reaction product of at least one amine-containing group, and optionally a second amine-containing group which includes a tertiary amine group, with a diepoxy- or diglycidyl compound and an additional amine compound subsequently reacted with unreacted epoxy groups. This polymeric composition is subsequently reacted with N-alkylating agent containing compounds to produce novel demulsifiers useful to demulsify oil bearing formations.Type: GrantFiled: December 20, 2001Date of Patent: March 17, 2009Assignee: Nalco CompanyInventors: Duane S. Treybig, Kin-Tai Chang, Dennis A. Williams
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Patent number: 7501087Abstract: An epoxy resin composition comprises (a) an epoxy resin, (b) an anionic polymerization initiator and (c) from 1 to 30 parts by weight per 100 parts by weight of epoxy resin (a) of an aromatic ring-containing proton donor of a polyhydric alcohol and/or a polymercaptan.Type: GrantFiled: October 26, 2006Date of Patent: March 10, 2009Assignee: Toray Industries, Inc.Inventors: Toshiya Kamae, Hiroki Oosedo, Go Tanaka, Shigeo Iwasawa
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Patent number: 7468454Abstract: 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: GrantFiled: June 30, 2005Date of Patent: December 23, 2008Assignee: Bayer MaterialScience AGInventor: Michael Mager
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Publication number: 20080269420Abstract: The shape memory polymers disclosed are a reaction product of at least one reagent containing two active amino-hydrogen or two active phenolic-hydrogen with at least one multifunctional cross linking reagent which contains at least three or more active amino- or phenolic-hydrogen or is a reagent containing at least three glycidyl ether moieties which is then further mixed with at least one diglycidyl ether reagent whereupon the resulting mixture is cured and has a glass transition temperature higher than 00C. This reaction creates crosslinking between the monomers and polymers such that during polymerization they form a crosslinked thermoset network.Type: ApplicationFiled: December 15, 2006Publication date: October 30, 2008Inventors: Tat Hung Tong, Benjamin J. Vining, Richard D. Hreha, Thomas J. Barnell
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Patent number: 7378461Abstract: 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: GrantFiled: October 31, 2002Date of Patent: May 27, 2008Assignee: Kawamura Institute of Chemical ResearchInventors: Kazutoshi Haraguchi, Akira Ohbayashi
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Patent number: 7312260Abstract: The invention relates to addition compounds suitable for use as wetting agents and dispersants and obtainable by reacting monofunctional or polyfunctional aromatic epoxides with polyoxyalkylenemonoamines having a number-average molecular weight of >400 g/mol, one primary or secondary amino group and at least 4 ether oxygen atoms per molecule, from 90 to 100% of the epoxide groups of the starting material having undergone reaction, the weight fraction of aromatic groups in the addition compounds being not more than 50% and the addition compounds containing per molecule at least one amino group on which salts can be formed, or being present as a salt. The invention also relates to a process for preparing the addition compounds, to their use as wetting agents and/or dispersants and to pigments or fillers coated with the addition compounds and to pigment pastes which comprise pigments, binders and the addition compounds of the invention.Type: GrantFiled: June 4, 2004Date of Patent: December 25, 2007Assignee: BYK-Chemie GmbHInventors: Udo Krappe, Karlheinz Haubennestel, Andrea Pentzek, Peter Matthee
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Patent number: 7189770Abstract: An amine curing component which can be used with various types of prepolymers including a urethane prepolymer having a reactive functional group of highly reactivity is provided. Also provided is a curable resin composition containing such curing component. This curable resin composition exhibits good surface and depth curability in the curing, and adjustment of pot life is also easy. The curing component contains an amino group-containing compound (A), a ketone compound (B), a ketimine compound (C), and water (D), and the curable resin composition contains this curing component.Type: GrantFiled: November 21, 2003Date of Patent: March 13, 2007Assignee: The Yokohama Rubber Co., Ltd.Inventors: Hiroyuki Okuhira, Akihito Kanemasa, Hiroyuki Hosoda
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Patent number: 7148294Abstract: An epoxy resin composition comprises (a) an epoxy resin, (b) an anionic polymerization initiator and (c) from 1 to 30 parts by weight per 100 parts by weight of epoxy resin (a) of an aromatic ring-containing proton donor of a polyhydric alcohol and/or a polymercaptan.Type: GrantFiled: March 27, 2002Date of Patent: December 12, 2006Assignee: Toray Industries, Inc.Inventors: Toshiya Kamae, Hiroki Oosedo, Go Tanaka, Shigeo Iwasawa
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Patent number: 7087799Abstract: An object of the present invention is to provide a material which resolves the drawbacks associated with polyimide polymers, and yet retains the advantages offered by conventional polyimide polymers. An amino group containing phenol derivative of the present invention is represented by a general formula (1) show below, and the present invention also provides a polyimide precursor produced using such an amino group containing phenol derivative. (wherein, R1, R2 and R3, which may be the same or different, each represent an alkyl group of 1 to 9 carbon atoms, an alkoxy group of 1 to 10 carbon atoms, a COOR group (in which R represents an alkyl group of 1 to 6 carbon atoms) or a hydrogen atom; R4 and R5, which may be the same or different, each represent an alkyl group of 1 to 9 carbon atoms or a hydrogen atom; X represents —O—, —S—, —SO2—, —C(CH3)2—, —CH2—, —C(CH3)(C2H5)—, or —C(CF3)2—; and n represents an integer of 1 or greater).Type: GrantFiled: January 31, 2003Date of Patent: August 8, 2006Assignee: Gun Ei Chemical Industry Co., Ltd.Inventors: Takeshi Tsuihiji, Michiyasu Yamazaki
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Patent number: 7014699Abstract: The invention relates to addition compounds of formula (1): in which: n is a number from 1 to 10; R1 and R2 are identical or different and are each a hydrogen atom or a saturated or unsaturated aliphatic radical having 1 to 4 carbon atoms; R3 and R4 are identical or different and are each a hydrogen atom or alkyl having 1 to 3 carbon atoms, and the bridge member (R3+R4) is in each case positioned ortho or meta in relation to the phenolic oxygen atom; Z represents a group —CH2—CH2—, —CH2—CH(CH3)—, —CH(CH3)—CH2— or a combination thereof; s is number from 1 to 200; B represents hydrogen, —CO—CH?CH—COOM, —COCH(SO3M)CH2COOM, —CO—CH2—CH(SO3M)—COOM, —SO3M, —SO2M and/or —PO3MM, whereby M is preferably a cation selected from the group Li+, Na+, K+, NH4+, HO—CH2—CH2—NH3+, (HO—CH2—CH2—)2NH2+ or (HO—CH2—CH2—)3NH+; and Y is a radical of an amine. The inventive addition compounds are used as dispersing agents of solids, for example, pigments, particularly in aqueous media.Type: GrantFiled: February 26, 2002Date of Patent: March 21, 2006Assignee: Clariant GmbHInventors: Martin Alexander Winter, Hans Joachim Metz, Andreas Harz, Andreas Pfrengle
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Patent number: 7005185Abstract: An epoxy composition includes an epoxy resin, a latent curing agent, and a catalyst. The composition includes two epoxide groups per molecule, and the latent curing agent is preferably a dicyanopolyamide, and most preferably dicyandiamide. The catalyst includes 2,4-toluene bis dimethyl urea, preferably in a concentration exceeding 70% by weight. The composition can be used in prepregs. The relative concentrations of the epoxy resin, curing agent, and catalyst are selected to achieve desired properties, including specific curing times and temperatures, and glass transition temperatures that enable a cured resin composition to be removed from a mold after being heated to its curing temperature, without being cooled. Exemplary formulations have reduced cure times, at both high and low curing temperatures, as compared to prior art formulations.Type: GrantFiled: November 27, 2002Date of Patent: February 28, 2006Assignee: Toray Composites (America), Inc.Inventors: Wei (Helen) Li, Kishio Miwa
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Patent number: 7001977Abstract: The present invention relates to adducts obtainable by reaction of: A) an amine compound containing 2 or more than 2 amino groups: with B) a polyalkylene glycol monoglycidyl ether of general formula (I), in which R independently of one another (for n>1), is an —H or —CH, radical, and n=1 to 50, characterized in that the reaction ratio of components A) and B) is selected in such a way that the resultant adduct contains 2 or more than 2 amine hydrogen groups: to curable compositions based on these adducts with epoxy resins, and to the use of these curable compositions as casting resin, adhesive, matrix resin, tooling resin or as coating composition, in particular for self-flowing coatings.Type: GrantFiled: March 6, 2002Date of Patent: February 21, 2006Assignee: Huntsman Advanced Materials Americas Inc.Inventors: Wolfgang Scherzer, Jörg Volle, Doris Fitzek
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Patent number: 6987161Abstract: Hardeners are provided for curing epoxies at lower temperatures than currently available hardeners while retaining superior mechanical and thermal properties. A first component is selected from imidazole, dicyandiamide, or a mixture of polyamines and tertiary amines. A poiyol mixture is then selected. The first component is combined with the polyol mixture to form a hardener. The hardener is combined with epoxy resin and is cured. A method for selecting a hardener to yield an epoxy-hardener system with good properties after curing at a specified temperature and time includes selecting components for the hardener so the glass transition temperature of the cured epoxy-hardener system is not significantly lower than 45° C. above the cure temperature. The method includes steps for adjusting and controlling the ultimate glass transition temperature to maximize the mechanical properties of the epoxy-hardener system. The method regularly produces hardened epoxy systems having about 90% or more epoxy groups reactect.Type: GrantFiled: April 25, 2003Date of Patent: January 17, 2006Assignee: Ardes Enterprise, Inc.Inventor: Richard D. Schile
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Patent number: 6946503Abstract: Provided herein are amine blends which may be used in place of N-aminoethyl piperazine as accelerator in the curing reaction of epoxy resins.Type: GrantFiled: April 8, 2003Date of Patent: September 20, 2005Assignee: Huntsman Petrochemical CorporationInventors: Bruce L. Burton, Chris E. Godinich
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Patent number: 6908982Abstract: 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: GrantFiled: June 18, 2003Date of Patent: June 21, 2005Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Tetsushi Ichikawa, Hisayuki Kuwahara, Masatoshi Echigo
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Patent number: 6838176Abstract: 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: GrantFiled: April 20, 2001Date of Patent: January 4, 2005Assignee: Mitsubishi Rayon Co., Ltd.Inventors: Kazuya Goto, Shigetsugu Hayashi, Tadayoshi Saito, Takashi Kaneko, Kazutami Mitani, Koki Wakabayashi, Yasuo Takagi
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Publication number: 20040254329Abstract: A curable mixture which includes at least (a) 10 to 100 percent by weight, in relation to the sum of the components (a) and (b), of at least one bi- or polyfunctional aromatic cyanate or a prepolymer formed from at least one bi- or polyfunctional aromatic cyanate or a mixture formed from the abovementioned cyanates and/or prepolymers; (b) 0 to 90 percent by weight, in relation to the sum of the components (a) and (b), of at least one mono-, bi- or polyfunctional epoxy resin; (c) 0.5 to 30 percent by weight, in relation to the sum of the components (a) and (b), of at least one mono-, bi- or polyfunctional aromatic amine; and (d) 0 to 5 percent by weight, in relation to the sum of the components (a) and (b), of at least one catalyst from the group consisting of transition metal compounds and boron trihalides.Type: ApplicationFiled: April 16, 2004Publication date: December 16, 2004Inventors: Ulrich Daum, Alessandro Falchetto, Sajal Das
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Publication number: 20040247882Abstract: The present invention relates to an epoxy resin composition for fiber reinforced composite material comprising the following components (1)-(3) as essential components, their mixing ratios meeting the following conditions (I)-(IV), and component (3) being dissolved homogeneously:Type: ApplicationFiled: April 27, 2004Publication date: December 9, 2004Inventors: Shinji Kouchi, Mariko Ishikawa, Hiroki Oosedo, Go Tanaka, Toshiya Kamae
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Patent number: 6812315Abstract: Disclosed is an oxazolidine compound represented by the following formula (1). [R1 represents a hydrocarbon group having 1 to 6 carbon atoms; R2 and R3 independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 15 carbon atoms, or R2 and R3 combine to form an alicyclic ring or an aromatic ring; R4 and R5 independently represent a methyl group or an ethyl group; R6 represents a single bond or —(R7—NHCOO—R8—OCONH)p—, R7 and R8 independently represent a divalent organic group, and p represents an integer of 1 to 15; m represents 2 or 3; n represents an integer of 1 to 3]. A curable resin composition using the oxazolidine compound as a latent curing agent have excellent curability and excellent storage stability, in particular, excellent storage stability in a state where the resin composition contains only the curable ingredient(s) and the latent curing agent.Type: GrantFiled: March 4, 2003Date of Patent: November 2, 2004Assignee: The Yokohama Rubber Co., Ltd.Inventor: Kazuo Suga
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Patent number: 6740359Abstract: The present invention is directed to fast dry ambient temperature curable coating compositions especially suited for use in automotive refinish applications. A binder component of the two pack coating composition includes an epoxy resin having at least one acetoacetate functionality and at least one epoxy group, and one or more reactive components provided with at least two acetoacetate functionalities. Some of the suitable reactive components include structured reactive diluent, an acrylic polymer, a polyester, or a combination thereof. A crosslinking component of the coating composition includes polyamine, a blocked polyamine or a mixture thereof. The present invention is further directed to a method of producing a coating on a substrate from the coating composition.Type: GrantFiled: January 25, 2002Date of Patent: May 25, 2004Assignees: E. I. du Pont de Nemours and Company, Renner Dupont Tintas Automotives E Industrials S.A.Inventors: Uday Kumar, Patrick H. Corcoran, Cesar A. Rodrigues
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Patent number: 6734263Abstract: The present invention provides a polymeric material and a process for making the polymeric material. The polymeric material has adhesive and noise abatement properties over a broad temperature range. Further, the material is chip and corrosion resistant and provides metal panel reinforcement.Type: GrantFiled: April 19, 2002Date of Patent: May 11, 2004Assignee: Diversified Chemical Technologies, Inc.Inventors: Rajan Eadara, Roy P. Jacob, Yushin Ahn, Biju Philip, Jori Joseff
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Patent number: 6727325Abstract: 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: GrantFiled: June 23, 1999Date of Patent: April 27, 2004Assignee: Nippon Soda Co. Ltd.Inventors: Hiroshi Suzuki, Satoru Abe, Izuo Aoki