Nitrogen Reactant Having At Least One Amino-nitrogen Atom Contains At Least One Aryl Group Patents (Class 528/124)
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Patent number: 11499004Abstract: A curing agent composition for an epoxy resin compound useful for the chemical fastening of construction elements, an epoxy resin compound, and a multi-component epoxy resin system are provided. Methods for the chemical fastening of construction elements in boreholes and the use of a salt (S) as an accelerator in an epoxy resin compound for chemical fastening are provided, the epoxy resin compound including a benzoxazine-amine adduct and an amine which is reactive to epoxy groups.Type: GrantFiled: September 9, 2019Date of Patent: November 15, 2022Assignee: Hilti AktiengesellschaftInventor: Nicole Behrens
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Patent number: 10711154Abstract: An hydrophobic epoxy resin composition including at least one ortho-substituted glycidyl ether, at least one ortho, ortho?-disubstituted glycidyl ether, at least one ortho, meta?-disubstituted glycidyl ether, at least one amine/aniline curing agent, and at least one organic solvent.Type: GrantFiled: January 19, 2018Date of Patent: July 14, 2020Assignee: The United States of America, as represented by the Secretary of the NavyInventors: Joseph W. Tsang, Michael Garrison
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Patent number: 10077361Abstract: A surface physical property modifier composition includes (A) a wax, (B) a vinyl (co)polymer, and (C) an aliphatic hydrocarbon having a carbon number of 5 to 14. Component (A) is set to be at least one selected from the group consisting of (a1) paraffin wax, (a2) microcrystalline wax, (a3) Fischer-Tropsch wax, and (a4) polyethylene wax, and component (B) is produced from at least one of (b1) a (meth)acrylonitrile, (b2) a (meth)acrylic acid having a carbon number of 1 to 4, (b3) a hydroxyethyl (meth)acrylate or hydroxypropyl (meth)acrylate, (b4) styrene, and (b5) predetermined (meth)acrylic acid alkyl esters. Component (A) is 50 to 98 parts by mass relative to 100 parts by mass of the total of (A) and (B), and component (C) is 0.001 to 1 percent by mass relative to the total amount of (A).Type: GrantFiled: October 6, 2015Date of Patent: September 18, 2018Assignee: NOF CORPORATIONInventors: Yusuke Sakata, Tomohisa Tasaka
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Patent number: 9321881Abstract: A liquid methylenedianiline product is disclosed. The product is produced by reacting aniline and ethylaniline with formaldehyde with an amine to formaldehyde ratio greater than about 2:1. The resulting reaction product is a liquid mixture of methylenedianiline, monoethyl methylenedianiline, and diethyl methylenedianiline having a viscosity of less than about 1000 cps at 40° C.Type: GrantFiled: August 12, 2011Date of Patent: April 26, 2016Assignee: Air Products and Chemicals, Inc.Inventors: Gauri Sankar Lal, Kristen Elaine Minnich, Pritesh G. Patel, Gamini Ananda Vedage, Garret C. Lau
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Patent number: 8981033Abstract: A curable resin comprising a curing agent, wherein the curing agent comprises an adjustable structural unit having a stable chain-like arrangement which is adjustable to a stable ring-like arrangement, wherein the ring-like arrangement comprises the constituents of the chain-like arrangement with two terminal constituents exhibiting an attractive chemical interaction, and is adjustable back from the ring-like arrangement to the chain-like arrangement by separation of the two terminal constituents.Type: GrantFiled: January 6, 2011Date of Patent: March 17, 2015Assignee: Hexcel Composites LimitedInventor: John Cawse
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Patent number: 8729213Abstract: 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: GrantFiled: September 23, 2011Date of Patent: May 20, 2014Assignee: Air Products and Chemicals, Inc.Inventors: Williams Rene Edouard Raymond, Gamini Ananda Vedage
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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: 8512594Abstract: 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: GrantFiled: August 25, 2008Date of Patent: August 20, 2013Assignee: Air Products and Chemicals, Inc.Inventors: Frederick Herbert Walker, Robert Marjo Theodoor Rasing, Gamini Ananda Vedage, Michael Ian Cook, Peter Andrew Lucas
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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: 8039537Abstract: A modified bismaleimide resin of Formula (I) or (II) is provided. In Formula (I) or (II), Q is —CH2—, —C(CH3)2—, —O—, —S—, —SO2— or null, R is —(CH2)2—, —(CH2)6—, —(CH2)8—, —(CH2)12—, —CH2—C(CH3)2—CH2—CH(CH3)—CH2—CH2—, 10<n<500, and x+y=n. The invention also provides a method for preparing a modified bismaleimide resin and a composition including the modified bismaleimide resin.Type: GrantFiled: February 22, 2010Date of Patent: October 18, 2011Assignee: Industrial Technology Research InstituteInventors: Feng-Po Tseng, Lu-Shih Liao, Kuo-Chan Chiou
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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: 7985808Abstract: The disclosure relates to composites having increased distortional deformation, and/or decreased dilatation load, as expressed within the von Mises strain relationship, which provide increased von Mises strain results. These composites may provide enhanced composite mechanical performances.Type: GrantFiled: April 23, 2010Date of Patent: July 26, 2011Assignee: The Boeing CompanyInventors: Stephen Christensen, James S. Senger
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Patent number: 7834126Abstract: The invention relates to amide-containing polymers of the general formula (I) A-X—CO—(CH2)2—NR1—R2—[Y—R3—Y—R4)a—B??(I) and also their salts with carboxylic acids, phosphoric esters and sulphonic acids. The invention further relates to processes for preparing the amide-containing polymers and to their use as rheology control agents.Type: GrantFiled: October 10, 2006Date of Patent: November 16, 2010Assignee: BYK-Chemie GmbHInventors: Karlheinz Haubennestel, Stefan Moessmer, Ulrich Orth, Daniela Betcke
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Patent number: 7745549Abstract: The invention relates to composites having increased distortional deformation, and/or decreased dilatation load, as expressed within the von Mises strain relationship, which provide increased von Mises strain results. These composites may provide enhanced composite mechanical performances.Type: GrantFiled: December 20, 2006Date of Patent: June 29, 2010Assignee: The Boeing CompanyInventors: Stephen Christensen, James S. Senger
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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: 7414097Abstract: 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: GrantFiled: March 5, 2007Date of Patent: August 19, 2008Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Hisayuki Kuwahara, Masatoshi Echigo, Takeshi Koyama
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Patent number: 7396902Abstract: 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: GrantFiled: February 9, 2004Date of Patent: July 8, 2008Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Hisayuki Kuwahara, Masatoshi Echigo, Takeshi Koyama
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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: 7307128Abstract: 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: GrantFiled: August 27, 2004Date of Patent: December 11, 2007Assignee: Japan Epoxy Resins Co., Ltd.Inventors: Atsuhito Hayakawa, Akihiro Itou
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Patent number: 7304120Abstract: 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: GrantFiled: January 26, 2007Date of Patent: December 4, 2007Assignee: Japan Epoxy Resins Co., Ltd.Inventors: Atsuhito Hayakawa, Akihiro Itou
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Patent number: 7282553Abstract: Polyamides and polyimides containing flexible isopropylidene, trifluoromethyl and tetramethyl substituents and their synthetic method are disclosed. Polyamide containing flexible isopropylidene, trifluoromethyl and tetramethyl substituents is synthesized by reacting diamine compound (2,2-bis[4-(2-trifluoromethyl-4-aminophenoxy)-3,5-dimethylphenyl]propane) with an equimolar diacid via a polycondensation reaction. Polyimide containing flexible isopropylidene, trifluoromethyl and tetramethyl substituents is synthesized by reacting diamine compound with an equimolar dianhydride via a polycondensation reaction.Type: GrantFiled: June 30, 2004Date of Patent: October 16, 2007Assignee: National Taiwan University of Science & TechnologyInventor: Der-Jang Liaw
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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: 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: 6962964Abstract: 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: GrantFiled: February 6, 2003Date of Patent: November 8, 2005Assignee: Air Products and Chemicals, Inc.Inventors: Michael Ulman, Gamini Ananda Vedage, David Alan Dubowik, Stephen Michael Boyce
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Patent number: 6951907Abstract: 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: GrantFiled: April 14, 2003Date of Patent: October 4, 2005Assignee: Henkel CorporationInventor: Mark M. Konarski
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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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Publication number: 20040266972Abstract: 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: ApplicationFiled: June 25, 2004Publication date: December 30, 2004Inventor: Jim Surjan
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Publication number: 20040242836Abstract: A curing agent for epoxy agent having N-phenyl-p-phenylenediamine(4-aminodiphenylamine). An epoxy resin combination having a main agent and a curing agent. The main agent has an epoxy resin. The curing agent has a N-phenyl-p-phenylenediamine(4-aminodiphenylamine).Type: ApplicationFiled: May 22, 2003Publication date: December 2, 2004Inventors: Brian S. Hayes, Richard Moulton, Doyle Dixon, Leonid Vorobyev
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Patent number: 6818318Abstract: 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: GrantFiled: April 14, 2003Date of Patent: November 16, 2004Assignee: Henkel CorporationInventor: Mark M. Konarski
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Patent number: 6809130Abstract: A halogen-free, phosphorus-free poly-cyclic compound is used a flame retardant. This compound has amide and hydroxy groups, and thus it is able to react with an epoxy resin to form a reactive type flame-retardant advanced epoxy resin. The advanced epoxy resin together with an inorganic additive are mixed with an epoxy resin to form a halogen-free, phosphorus-free flame-retardant epoxy composition, which can be used in the manufacture of a printed circuit board and as an encapsulation material for a semi-conductor device.Type: GrantFiled: March 11, 2003Date of Patent: October 26, 2004Assignee: Industrial Technology Research InstituteInventors: Kuo-Chan Chiou, Tzong-Ming Lee, Feng-Po Tseng, Lu-Shih Liao, Jia-Chi Huang, Tzu-Ting Lin
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Patent number: 6770370Abstract: An adhesive composition for semiconductor device, comprising 10 to 30% by weight of a reactive elastomer (A), 40 to 65% by weight of an epoxy resin (B) having two or more glycidyl ether groups, a phenol resin (C) and a curing accelerator (D), wherein a ratio of the epoxy resin (B) to the phenol resin (C) is within a range from 1:0.6 to 1:1 in terms of a functional group equivalent ratio, and an adhesive sheet for a semiconductor device using the same are provided. The composition and the sheet are superior in reflow resistance and short-time and low-temperature bonding without lowering characteristics such as heat resistance, low hygroscopicity, high adhesion and electrical insulating properties of an epoxy resin cured article.Type: GrantFiled: August 5, 2002Date of Patent: August 3, 2004Assignee: Tomoegawa Paper Co., Ltd.Inventors: Naoji Suzuki, Osamu Oka, Jun Tochihira, Akihiro Maeda
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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
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Patent number: 6723763Abstract: The present invention provides a new class of materials effective as accelerators for curing anaerobic adhesives. The addition of these materials into anaerobic adhesives as a replacement for conventional curatives, such as APH and/or toluidines, surprisingly provides at higher cure speeds and comparable physical properties for the reaction products formed therefrom.Type: GrantFiled: March 15, 2002Date of Patent: April 20, 2004Assignee: Henkel Loctite CorporationInventors: Qinyan Zhu, Shabbir Attarwala
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Patent number: 6723821Abstract: The invention features a polyamine epoxide adduct, prepared by admixing a source of epoxy group with a polyamine, and allowing the epoxy groups to react with the terminal amino groups of the polyamine so as to form the polyamine epoxy adduct. The polyamine epoxide adduct of the invention can be used as a component for preparing a polyurea polymer, thereby providing the resulting polyurea polymer with improved adhesiveness and greater chemical resistance to acidic conditions. Polyurea polymer coatings prepared from polyamine epoxide adducts demonstrate better chemical resistance and adhesion when applied to substrates than do conventionally prepared polyurea formulations.Type: GrantFiled: February 19, 2002Date of Patent: April 20, 2004Assignee: Hehr, International Inc.Inventor: Stuart B. Smith
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Patent number: 6670430Abstract: 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: GrantFiled: November 20, 2000Date of Patent: December 30, 2003Assignee: Henkel Loctite CorporationInventor: Mark M. Konarski
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Patent number: 6646064Abstract: A method for imparting flame retardance to an epoxy resin comprises reacting an epoxy resin with a phosphorus-containing dihydric phenol or naphthol derived from the reaction of 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (i.e., DOPO) with a benzoquinone or naphthoquinone.Type: GrantFiled: September 10, 2001Date of Patent: November 11, 2003Assignee: National Science CouncilInventors: Chun-Shan Wang, Jeng-Yueh Shieh
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Patent number: 6627684Abstract: The present invention discloses a dielectric composition having two steps of laminating temperatures. The composition is comprised of: a diamine curing agent containing asymmetrical chemical structures with different reactivity; an epoxy resin compound, containing at least two epoxy groups; and inorganic powder. In addition, flame retardant and toughener are added dependent on the requirements.Type: GrantFiled: December 18, 2001Date of Patent: September 30, 2003Assignee: Industrial Technology Research InstituteInventors: Tzong-Ming Lee, Hsun-Tien Li, Kai-Chi Chen, Mei-Ling Chen
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Patent number: 6617399Abstract: 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: GrantFiled: November 19, 2001Date of Patent: September 9, 2003Assignee: Henkel Loctite CorporationInventor: Mark M. Konarski
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Patent number: 6569983Abstract: A water-soluble branched polyhydroxyetheramine, wherein the branched polyhydroxyetheramine is prepared by reacting an amine having two reactive hydrogen atoms with a diepoxide to form a polyhydroxyetheramine and then reacting the polyhydroxyetheramine with an N-alkylating agent, an aqueous composition comprising the branched polyhydroxyetheramine and use of the branched polyhydroxyetheramine to modify the permeability to water of a subterranean formation are disclosed.Type: GrantFiled: December 20, 2001Date of Patent: May 27, 2003Assignee: Ondeo Nalco Energy Services, L.P.Inventors: Duane Treybig, Kin-Tai Chang, Dennis Williams
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Patent number: 6538052Abstract: The invention relates to curable compositions comprising a) an epoxy resin, b) an aminic curing agent and c) a curing accelerator, which comprise as curing accelerator c) at least one or more than one compound selected from c1) a compound of formula (I) wherein R1 and R2 are each independently of the other a hydrocarbon radical having from 1 to 12 carbon atoms, c2) a reaction product of a compound of formula (I) with formaldehyde, and c3) a reaction product of a compound of formula (I) with formaldehyde and a phenolic compound, in an amount of from 0.1 to 25% by weight, based on the sum of components a), b) and c), and to a process for the production of cured products using those compositions.Type: GrantFiled: June 28, 2001Date of Patent: March 25, 2003Assignee: Vantico GmbH & Co.Inventors: Wolfgang Scherzer, Jörg Volle
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Patent number: 6500912Abstract: A curable epoxy composition comprises an epoxy resin having at least 1.5 epoxy groups per molecule and an amine-terminated polyamide. The liquid amine-terminated polyamide is prepared by reacting a long-chain, C20-C60 dicarboxylic acid or derivative with an amine having a general formula of R1—NH—R2—NH—R3.Type: GrantFiled: September 12, 2000Date of Patent: December 31, 2002Assignee: Resolution Performance Products LLCInventor: Larry Steven Corley
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Patent number: 6485834Abstract: A thermosetting composition with a glass transition temperature of at least 100° C. comprises at least one epoxy resin formed from at least one polyepoxide containing at least two epoxy groups in its molecule and at least one aromatic polyamine containing at least two primary amino groups in its molecule, at least one alkanoyl substituent containing 1 to 12 carbon atoms located in the position alpha to one of the amino groups. The molar ratio of the amine to the epoxide is such that each amine group corresponds to 1.6 to 2.6 epoxy groups. The composition also includes a flow controller. The composition can be used as a protective coating for any metallic or non metallic surface. The invention also concerns a flexible deployable preform comprising the composition.Type: GrantFiled: November 20, 2000Date of Patent: November 26, 2002Assignee: Institut Francais du PetroleInventors: Paul Mariaggi, Henri Delhomme, Dominique Audigier, Frédérique Jacquemin-Hauviller
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Patent number: 6476160Abstract: 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: GrantFiled: July 16, 1999Date of Patent: November 5, 2002Assignee: The Yokohama Rubber Co., Ltd.Inventors: Hiroyuki Okuhira, Naoya Adachi
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Patent number: 6475621Abstract: The subject invention pertains to an aqueous primer for use on metal surfaces to which a composite or a metal adherend is bonded. The primer composition includes an aqueous dispersion of: (a) at least one thermosetting resin curable at an elevated temperature; (b) at least one organosilane, each said organosilane containing at least ore hydrolyzable group; and (c) a curing agent. The aqueous primer composition contains substantially no volatile organic solvent, is environmentally superior to solvent-based primers, is storage stable, exhibits excellent solvent resistance and performs without loss of physical properties.Type: GrantFiled: September 11, 1998Date of Patent: November 5, 2002Assignee: Cytec Technology Corp.Inventors: Dalip Kohli, Elaine Dickerson
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Patent number: 6465598Abstract: 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: GrantFiled: February 26, 2001Date of Patent: October 15, 2002Assignee: Tennant CompanyInventors: Joseph S. Keute, Anne-Marie Thunnissen, Robert J. Tweedy, Jr.
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Poly(hydroxy amino ether) composition, method for preparing the same and articles prepared therefrom
Patent number: 6455116Abstract: A composition comprising a poly(hydroxy aminoether) and an effective amount of a propoxylated or ethoxylated phenol, process for preparing the same and articles prepared from the composition.Type: GrantFiled: September 14, 2001Date of Patent: September 24, 2002Assignee: Dow Global Technologies Inc.Inventors: Guang-Ming Xia, John M. Beckerdite, Wendy D. Hoenig -
Patent number: 6451931Abstract: 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: GrantFiled: December 29, 2000Date of Patent: September 17, 2002Assignee: Asahi Denki Kogyo Kabushiki KaishaInventors: Akio Ogawa, Manabu Abe
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Patent number: 6410127Abstract: 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: GrantFiled: November 8, 2001Date of Patent: June 25, 2002Assignee: Toray Industries, Inc.Inventors: Toshiya Kamae, Hiroki Oosedo, Shunsaku Noda, Shinji Kouchi, Ryuji Sawaoka
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Patent number: 6380344Abstract: A cyanate ester-epoxy resin composition that can be cured to obtain a product which has excellent mechanical properties is provided. More particularly, a cyanate ester composition comprising (A) a cyanate ester in which the total content of impurities containing imino carbonates, alkyl cyanamides, partially substituted cyanates and phenols is 5% or less, or a prepolymer thereof and (B) an epoxy resin is provided.Type: GrantFiled: May 11, 1999Date of Patent: April 30, 2002Assignee: Sumitomo Chemical Company, Ltd.Inventors: Toshiaki Hayashi, Nobuyuki Nakajima