Material Contains A Boron Atom Patents (Class 528/91)
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Patent number: 8883937Abstract: A cyclic compound represented by formula (1): wherein L, R1, R?, and m are as defined in the specification. The cyclic compound of formula (1) is highly soluble to a safety solvent, highly sensitive, and capable of forming resist patterns with good profile. Therefore, the cyclic compound is useful as a component of a radiation-sensitive composition.Type: GrantFiled: August 27, 2010Date of Patent: November 11, 2014Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Masatoshi Echigo, Hiromi Hayashi
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Publication number: 20140088282Abstract: A mixture may include at least one polymerizable species and at least one thermoresponsive supramolecular initiator complex involving a host-guest interaction. Processes for making resins may include mixing at least one polymerizable species with at least one thermoresponsive supramolecular initiator complex involving a host-guest interaction; subjecting the mixture to a temperature above about 30° C. thereby promoting the dissociation of the at least one thermoresponsive supramolecular initiator; and allowing the mixture to cure at the temperature for a period of time.Type: ApplicationFiled: August 12, 2013Publication date: March 27, 2014Inventors: THOMAS VIDIL, FRANCOIS-GENES TOURNILHAC, LUDWIK LEIBLER
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Patent number: 8436126Abstract: The present invention provides a resin composition for an adhesive sheet, comprising an acrylic copolymer containing (A) an acrylate ester, methacrylate ester, or a mixture thereof, (B) acrylonitrile, methacrylonitrile, or a mixture thereof, and (C) an unsaturated carboxylic acid; an epoxy resin; and a curing agent, wherein the curing agent comprises at least one selection from Lewis acid-amine complexes.Type: GrantFiled: July 17, 2007Date of Patent: May 7, 2013Assignee: Arisawa Mfg. Co., Ltd.Inventors: Shinichi Hasegawa, Fumiki Higuchi, Toru Ueki
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Patent number: 8426547Abstract: A phosphorus-containing epoxy resin and a method for synthesizing the same are disclosed. The method includes the step of catalytically reacting compound (i) with compound (ii) to synthesize the phosphorus-containing epoxy resin having the structure of compound (I). R is methyl or phenyl, and n is the integer from 1 to 9.Type: GrantFiled: March 29, 2010Date of Patent: April 23, 2013Assignee: Chang Chun Plastics Co., LtdInventors: Fang-Hsien Su, Chi-Hung Liu, Chun-Hsiung Kao, An-Pang Tu, Kuen-Yuan Hwang
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Patent number: 8383862Abstract: Provided are a salt compound, cationic polymerization initiator and cationically polymerizable composition, which have a superior acid-generating capacity and high sensitivity, and are free from coloration. The salt compound is represented by the following general Formula (1): (wherein, R01 to R05 each independently represents a group selected from a hydrogen atom, a fluorine atom and —YR group, one of the R01 to R05 being a —YR group and at least two of the R01 to R05 being fluorine atoms; Y represents an oxygen atom or a sulfur atom; R represents a C1-C4 alkyl group; Ctp+ represents a p-valent cation, the p being 1 or 2; and n represents a coefficient required for maintaining electrical neutrality).Type: GrantFiled: October 28, 2008Date of Patent: February 26, 2013Assignee: Adeka CorporationInventors: Kentaro Kimura, Shohei Fujita, Tomoya Tamachi
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PROCESS FOR CONTINUOUS PREPARATION OF A PREPOLYMER BASED ON PHENOLIC RESINS, OXAZOLINES AND EPOXIDES
Publication number: 20120121812Abstract: Process for the continuous preparation of prepolymers based on phenolic resin, an oxazoline component and an epoxide in the presence of a catalyst, including supplying the phenolic resin and the oxazoline component to an extruder in a stream A; a Lewis adduct of boron trifluoride or of aluminium trichloride, or arylsulphonic acids or alkylsulphonic acids, or latent arylsulphonic acids or latent alkylsulphonic acids, in a stream B, and the epoxide in a stream C, the infeed of stream A being situated, as seen in extrusion direction, before the infeed of stream C, these reactants are mixed at a reaction temperature of 120 to 200° C. with a residence time in the extruder of 3 seconds to 15 minutes, and then the product discharge of the extruder is cooled to a temperature of less than 45° C. within from 30 to 60 seconds.Type: ApplicationFiled: November 16, 2011Publication date: May 17, 2012Applicant: EVONIK DEGUSSA GmbHInventors: Marianne OMEIS, Franz-Albert von Itter, Thomas Weihrauch -
Publication number: 20110172384Abstract: A phosphorus-containing epoxy resin and a method for synthesizing the same are disclosed. The method includes the step of catalytically reacting compound (i) with compound (ii) to synthesize the phosphorus-containing epoxy resin having the structure of compound (I). R is methyl or phenyl, and n is the integer from 1 to 9.Type: ApplicationFiled: March 29, 2010Publication date: July 14, 2011Applicant: CHANG CHUN PLASTICS CO., LTDInventors: Fang-Hsien SU, Chi-Hung LIU, Chun-Hsiung KAO, An-Pang TU, Kuen-Yuan HWANG
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Patent number: 7479534Abstract: The present application relates to a one-component epoxy resin composition that contains an epoxy resin containing: (1) an epoxy resin having 2 or more epoxy groups in the molecule, (2) a polythiol compound having 2 or more thiol groups in the molecule, (3) a compound that releases a basic component under a curing temperature condition and dissolves in constituent (2), and (4) a compound having Lewis acidity. The present invention also relates to a method of producing the same.Type: GrantFiled: July 24, 2006Date of Patent: January 20, 2009Assignee: Ajinomoto Co., Inc.Inventors: Hiroshi Amano, Osamu Yamabe, Hiroyasu Koto
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Patent number: 7368524Abstract: The invention relates to two-component preparations comprising epoxy compounds and a noble metal species, in particular for the preparation of dental compositions. The invention particularly relates to two-component dental compositions which comprise epoxy compounds and are cured by cationic polymerization in the presence of a noble metal species.Type: GrantFiled: April 19, 2005Date of Patent: May 6, 2008Assignee: 3M Innovative Properties CompanyInventors: Adrian S. Eckert, Uwe H. Hoheisel, Reinhold Hecht
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Patent number: 7112635Abstract: Non-gelled polymeric polyols are prepared by the acid catalyzed copolymerization of water, tetrahydrofuran and multifunctional epoxy resins. The polyols can be cured with OH reactive crosslinkers such as amino resins and polyisocyanates to yield thermosetting coatings with useful properties.Type: GrantFiled: March 12, 2004Date of Patent: September 26, 2006Assignee: Air Products and Chemicals, Inc.Inventor: Frederick Herbert Walker
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Patent number: 7026411Abstract: Curable composition comprising at least one polyaromatic having reactive end groups, at least one thermoset resin, and a reactive catalyst, wherein the reactive end groups are adapted to react with the catalyst, characterized in that the catalyst comprises a Lewis acid having amine functionality, suitably the catalyst is of the formula: LXn.R where LXn is a Lewis acid and R is a amine; process for the preparation thereof; method for curing thereof; cured products and prepreg; and method for cure cycle design.Type: GrantFiled: November 6, 2000Date of Patent: April 11, 2006Assignee: Cytec Technology Corp.Inventors: Jeffrey Thomas Carter, Carmelo Lo Faro
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Patent number: 7008555Abstract: 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: GrantFiled: May 22, 2003Date of Patent: March 7, 2006Assignee: Applied Poleramic Inc.Inventors: Brian S. Hayes, Richard Moulton, Doyle Dixon, Leonid Vorobyev
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Patent number: 6949592Abstract: The invention relates to novel liquid epoxy resin emulsions which contain the following components, dissolved and/or dispersed in water: (A) at least one binding agent selected from the group made of epoxy resins and modified epoxy resins, (B) at least one non ionic thickener and (C) at least one catalyst for hardening, produced by reacting at least one boron trifluoride complex with at least one compound containing at least one epoxy group. The invention also relates to a method for the production and use thereof as an impregnating varnish for electrotechnical components, particularly for electrical winding items.Type: GrantFiled: February 6, 2002Date of Patent: September 27, 2005Assignee: Dres. Fitznee, Muench & KluinInventors: Klaus-Wilhelm Lienert, Gerold Schmidt, Sascha Tödter-König
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Patent number: 6894144Abstract: The invention relates to elastomer materials based on N-alkylaziridino compounds with a base component which contains the aziridino compounds and with a catalyst component which contains at least one acid-acting compound, both components being mixed before use, characterized in that, as acid-acting compound of the catalyst component, one or more boric acid complexes are used which can be obtained by reaction of boric acid and/or a boric acid derivative with at least one OH-functional compound, the OH functions being able to be present wholly or partly protected, and this reaction being carried out either as an upstream reaction between boric acid and/or a boric acid derivative and at least one such OH-functional compound or during or after the preparation of the catalyst component or by mixing the catalyst component with the base component which then contains at least one OH-functional compound.Type: GrantFiled: September 1, 2000Date of Patent: May 17, 2005Assignee: 3M Espe AGInventors: Joachim Zech, Gunther Eckhardt, Cornelia Führer, Bernd Gangnus, Andreas Rombach, Oswald Gasser, Thomas Klettke, Erich Wanek
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Publication number: 20040254328Abstract: 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: ApplicationFiled: April 20, 2004Publication date: December 16, 2004Inventors: Kazutoshi Haraguchi, Akira Ohbayashi
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Patent number: 6800717Abstract: Non-gelled polymeric polyols are prepared by the acid catalyzed copolymerization of epoxy resins and water. When the starting resin is an epoxy resin derived from bisphenol-A, the resulting product has much lower levels of bisphenol-A and diglycidyl ether of bisphenol-A (DGEBA) compared to traditional epoxy resins of comparable molecular weight prepared by the advancement process. The product can be cured with OH reactive crosslinkers such as amino resins and polyisocyanates to yield thermosetting coatings with useful properties.Type: GrantFiled: January 31, 2002Date of Patent: October 5, 2004Assignee: Air Products and Chemicals, Inc.Inventors: Frederick Herbert Walker, John Bartram Dickenson
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Publication number: 20040147711Abstract: Epoxy resin compositions including a boron atom containing compound, and preferably a multiple boron atom containing compound, are disclosed. The resin compositions exhibit enhanced properties such as cure time and glass transition temperature “Tg” and are particular suited to be utilized in the manufacture of composites, especially prepregs used for the manufacture of composite structures.Type: ApplicationFiled: January 23, 2003Publication date: July 29, 2004Inventors: Walter H. Christiansen, Larry S. Corley
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Patent number: 6703124Abstract: The present invention relates to a nonflammable epoxy resin composition for using a thin copper film laminate, which is applied to a printed circuit board (PCB), and using the same. The present invention provides for nonflammable epoxy resin composition for using a thin copper film laminate, comprising bisphenol A-type epoxy resin, multifunctional epoxy resin, an imidazole-based curing catalyst, and a curing retarder, and using the same. As described above, since the ring-open of the epoxy group is prompted by an imidazole catalyst, without the use of dicyandiamide, epoxy polymer reaction occurs due to the chain-reaction of epoxy group, and the glass-transition temperature is 170° C. or greater, the nonflammable epoxy resin composition for using a thin copper film of the present invention has a strong heat-resistance, lower dielectric constant, controllable gelation time, and does not require the use of non-harmful catalysts to the human body.Type: GrantFiled: February 8, 2002Date of Patent: March 9, 2004Assignee: LG Chemical Co., Ltd.Inventors: Young-Sik Kim, Hyun-Cheol Kim, Dong-Rak Shin
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Patent number: 6670017Abstract: Photocurable compositions and process for providing form-in-place gaskets using automated placement followed by photocuring of a pattern of a non-silicone composition comprising a liquid polyolefin oligomer, a reactive diluent, and a curative. The form-in-place gasket, after curing, has a level of total outgassing components of about 10 &mgr;g/g to about 45 &mgr;g/g. The curative responds to actinic radiation and heat, and may contain a photoinitiator. Optionally a photocurable, form-in-place gasket according to the present invention further comprises a thixotropic filler in an amount from about 8.0 wt. % to about 12.0 wt. %, and preferably comprises a fumed silica.Type: GrantFiled: September 4, 2001Date of Patent: December 30, 2003Assignee: 3M Innovative Properties CompanyInventors: Mitchell Huang, Michael A. Kropp
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Patent number: 6652281Abstract: Dental materials containing monomers and/or prepolymers can be subjected to a polymer-forming reaction. The dental materials comprise at least one initiating system and optionally comprise fillers, colorants, flow modifiers, stabilizers, ion-releasing substances as well as compounds which increase X-ray capacity or other modifiers. The dental materials are characterized in that the initiating system is proportioned such that the dental materials are sufficiently capable of flowing for at least 10 seconds after exposure to oxygen, whereupon they subsequently harden into a solid material.Type: GrantFiled: February 5, 2002Date of Patent: November 25, 2003Assignee: 3M ESPE AGInventors: Gunther Eckhardt, Thomas Luchterhandt, Thomas Klettke
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Patent number: 6649728Abstract: A catalyst for curing epoxy resins comprises a tetraalkylphosphonium tetrafluoroborate represented by Formula (1): wherein R1, R2, R3, and R4 are each C1-C5 linear or branched alkyl and may be the same or different, and the halogen ion content in the tetraalkylphosphonium tetrafluoroborate is 20 ppm or less. An epoxy resin powder coating composition containing this catalyst exhibits a prolonged pot life and can be baked at decreased temperatures.Type: GrantFiled: July 3, 2002Date of Patent: November 18, 2003Assignee: Nippon Chemical Industrial Co., Ltd.Inventors: Hiroshi Kawakabe, Masashi Sugiya, Yoshifusa Hara
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Patent number: 6642344Abstract: A method for making flexible epoxy resins by curing an epoxide and a bis-phenol with an aliphatic secondary diamine having the structural formula (I) or (II): where R1 and R2 are each individually an alkyl, alkenyl, aryl, or arylalkyl group having from about 1 to about 20 carbon atoms, and R3 and R4 are each individually an alkyl or alkenyl group having from about 1 to about 20 carbon atoms, or hydrogen.Type: GrantFiled: January 22, 2002Date of Patent: November 4, 2003Assignee: Dorf Ketal Chemicals, LLCInventors: David W. House, Ray V. Scott, Jr.
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Patent number: 6613839Abstract: An epoxy resin composition comprises a) a polyepoxide, b) a cure inhibitor of boric acid, a Lewis acid derivative of boron, an alkyl borane, a mineral acid having a nucleophilicity value “n” of greater than zero and less than 2.5, or an organic acid having a pKa value of 1 or more, a catalyst which can be complexed with the cure inhibitor, and c) more than 30 parts by weight per 100 parts by weight of polyepoxide of a cross-linker such as a polycarboxylic acid or anhydride including a copolymer of an ethylenically unsaturated anhydride and a vinyl compound, or a hydroxy-functional compound such as a copolymer of styrene and hydroxystyrene.Type: GrantFiled: January 20, 1998Date of Patent: September 2, 2003Assignee: The Dow Chemical CompanyInventors: Joseph Gan, John P. Everett
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Patent number: 6599960Abstract: The invention relates to preparations with improved curing behavior, which are characterized in that they contain 0.0005 to 50 wt. % of soluble and/or fine-particle organic and/or inorganic alkaline earth and/or alkali metal compounds. The preparations according to the invention may be used for bonding, sealing, casting and coating substrates, also in medical dental and technical dental preparations, and for making impressions of articles and, more particularly, for making dental impressions.Type: GrantFiled: July 13, 2000Date of Patent: July 29, 2003Assignee: Espe Dental AGInventors: Gunther Eckhardt, Gunther Lechner, Erich Wanek, Ursula Somnitz
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Patent number: 6420460Abstract: The present invention relates to a thermally and cationically curable composition containing triarylcyclopropenylium salts and a solvent that is a Lewis base which contains acidic hydrogen and their use as thermal initiators in polymerization processes. The present invention includes the polymerization of epoxy resins, vinyl ethers and other cationically curable monomers.Type: GrantFiled: February 12, 2001Date of Patent: July 16, 2002Assignee: UCB S.A.Inventors: Wenqin Zhang, John H. Malpert, Douglas C. Neckers, Dustin B. Martin
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Patent number: 6387310Abstract: A thermosetting resin composition for prestressed concrete tendon, wherein the composition does not harden until the completion of the straining of the tendon, which is the inherent object in the post-tension technique, even if the heat storage temperature in the concrete structures elevates from 30° C. to 80° C. or higher due to heat of hydration reaction in setting a concrete, particularly 95° C. that is the maximum temperature in solidifying a concrete, and the composition including the site of 30° C. or lower where there is substantially no partial heat storage due to heat of hydration reaction in setting the concrete hardens within the prescribed period of time under spontaneous environmental temperature after the subsequent natural cooling, thereby achieving anti-rust and anti-corrosion of the tendon and also adhesion and integral bonding of the tendon and the concrete, a use method thereof and a prestressed concrete tendon.Type: GrantFiled: April 25, 2000Date of Patent: May 14, 2002Assignees: Mitsui Chemicals, Inc., Shinko Wire Company, Ltd.Inventors: Hiroshi Iizuka, Toshio Kobayashi, Mutsuhiko Ohnisi, Seiichiro Hirata
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Patent number: 6352783Abstract: A copolyester blend resistant to ultraviolet radiation consists essentially of a polyethylene terephthalate based copolyester having 1,4-cyclohexanedimethanol residues; an effective amount of an ultraviolet radiation absorber selected from the group consisting of benzoxazinones, dimeric benzotriazoles, triazines and mixtures thereof; and from about 2 to about 25 mole percent of 4,4′-biphenyldicarboxylic acid residues present in the copolyester wherein the mole percent is based on 100 mole percent of dicarboxylic acid or equivalents. The copolyester blend is useful in making UV radiation resistant thermoformed articles.Type: GrantFiled: December 13, 1999Date of Patent: March 5, 2002Assignee: Eastman Kodak CompanyInventor: David Richard Fagerburg
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Patent number: 6316049Abstract: Coating compositions comprising an epoxy resin and a curative which is methylenedisalicylic acid and/or a methylendisalicylic acid ring-substituted homologue are found to cure at and produce a wrinkle finish at relatively low temperatures when a borontrifluoride:amine complex is used as the cure catalyst.Type: GrantFiled: January 4, 2000Date of Patent: November 13, 2001Assignee: Rohm and Haas CompanyInventors: Owen H. Decker, Charles P. Tarnoski, Michele L. Cramer
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Patent number: 6232426Abstract: Disclosed herein is a one-part polythiol-type epoxy resin composition having an excellent low-temperature quick curability and a good storage stability (shelf stability), which can be prepared by using, as essential components, (1) an epoxy resin having two or more epoxy groups per one molecule, (2) a thiol compound having two or more thiol groups per one molecule, (3) a solid dispersion-type latent curing accelerator and (4) a borate ester compound.Type: GrantFiled: February 23, 1999Date of Patent: May 15, 2001Assignee: Ajinomoto Co., Inc.Inventors: Hiroshi Orikabe, Kiyomiki Hirai
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Patent number: 5959061Abstract: Water-dispersible curing agents for epoxy resins are disclosed which, as a mixture with epoxy resins, have a potlife indication by showing the end of the processing time by a clear increase in viscosity, and which comprise reaction products (ABC) of adducts of aliphatic polyols (A) with a weight-average molar mass of from 200 to 20, 000 g/mol, comprising at least one polyol (A1) having a molar mass of less than 4000 g/mol, and at least one polyol (A2) having a molar mass of more than 4000 g/mol, and at least one epoxide compound (B) having at least two epoxide groups per molecule, and a specific epoxide group content of from 500 to 10 000 mmol/kg, (A1) and (A2) being reacted separately or as a mixture with (B), and then reacting this adduct with one or more polyamines (C) having at least three amine hydrogen atoms and at least one primary amino group per molecule, the ratio of the number of hydroxyl groups of component (A) to the number of epoxide groups of component (B) being 1:3 to 1:10, and the ratio of thType: GrantFiled: July 25, 1997Date of Patent: September 28, 1999Assignee: Vianova Resins GmbHInventors: Uwe Neumann, Martin Gerlitz
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Patent number: 5955551Abstract: The present invention relates to polyglycidyl ether compounds containing at least three mono- or divalent radicals A of the general formula wherein R.sub.Type: GrantFiled: August 6, 1997Date of Patent: September 21, 1999Assignee: Ciba Specialty Chemicals CorporationInventors: Chi-Wen Frank Cheng, Mark Bryant
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Patent number: 5759692Abstract: The invention relates to expandable, halogen-free, flame-retardant coating compositions comprising epoxy resins, polyphosphoric esters and a curing agent, which composition comprises from 75 to 95 parts by weight of epoxy resin and from 5 to 25 parts by weight of polyphosphoric ester and wherein the overall weight ratio of epoxy resin and polyphosphoric ester to curing agent is (1.1 to 10) to 1. The invention likewise relates to a process for preparing such expandable, halogen-free coating flame-retardant, compositions comprising epoxy resins and polyphosphoric esters and a curing agent, and to their use, in particular as an intumescent coating.Type: GrantFiled: March 3, 1997Date of Patent: June 2, 1998Assignee: Hoechst AktiengesellschaftInventors: Guido Scholz, Sebastian Harold, Wolf-Dieter Pirig
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Patent number: 5759691Abstract: The invention relates to an expandable, halogen-free, flame-retardant coating composition comprising epoxy resins, polyphosphoric/polyphosphonic esters and a curing agent, which composition comprises from 75 to 95 parts by weight of epoxy resin and from 5 to 25 parts by weight of polyphosphoric/polyphosphonic ester and wherein the overall weight ratio of epoxy resin and polyphosphoric/polyphosphonic ester to curing agent is (1.1 to 10) to 1. The invention likewise relates to a process for preparing such coating compositions and to their use.Type: GrantFiled: March 3, 1997Date of Patent: June 2, 1998Assignee: Hoechst AktiengesellschaftInventors: Guido Scholz, Sebastian Horold, Wolf-Dieter Pirig
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Patent number: 5721323Abstract: A class of compounds which inhibits the reaction of a polyepoxide with a curing agent at low temperatures including an epoxy resin composition containinga) a polyepoxide;b) an amine or amide curing agent for the polyepoxide;c) at least about 15 meq (per equivalent of polyepoxide) of a catalyst for the reaction of the polyepoxide with the curing agent; andd) a cure inhibitor selected such that:(1) at about 171.degree. C. the composition has a gel time that is at least about 50 percent longer than a similar composition without the inhibitor, and(2) at about 175.degree. C. and higher the composition cures in no more than about 50 minutessuch that the composition cures rapidly with high cross-link density because it has a high catalyst loading, while the inhibitor lengthens the gel time to permit laminating and other processing.Type: GrantFiled: December 27, 1996Date of Patent: February 24, 1998Assignee: The Dow Chemical CompanyInventors: Craig E. Schultz, James L. Bertram, William A. Clay, Guang-Ming Xia, Joseph Gan
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Patent number: 5652322Abstract: Heat-curable epoxy resin systems comprising(a) at least one epoxy resin,(b) at least one polycarboxylic acid anhydride, and(c) 1,4-diazabicyclo(2,2,2)octane or a C.sub.1 -C.sub.4 alkyl-substituted derivative of 1,4-diazabicyclo(2,2,2)octane as curing accelerator, andwherein one portion of the curing accelerator (c) is replaced by(d) a complex of a boron halide with an amine,have good reactivity at elevated temperatures and comparatively high stability at temperatures below c. 80.degree. C.Type: GrantFiled: September 17, 1996Date of Patent: July 29, 1997Assignee: Ciba-Geigy CorporationInventors: Roland Moser, Daniel Bar
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Patent number: 5623023Abstract: Disclosed is a curable composition comprising (A) an imidazole derivative represented by the following general formula (1), which is capable of generating free imidazole by exposure to light, and (B) a polyfunctional epoxy compound: ##STR1## wherein R represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, an aralkyl group, a nitro group, a cyano group, an alkoxyl group, a phenoxy group, or an aromatic ring residue capable of forming a condensed ring in combination with a benzene ring. The composition may further incorporate therein at least one compound selected from the group consisting of polyfunctional phenol compounds, polyfunctional carboxylic acids, acid anhydrides, and amine compounds.Type: GrantFiled: May 21, 1996Date of Patent: April 22, 1997Assignee: Taiyo Ink Manufacuturing Co., Ltd.Inventor: Tadatomi Nishikubo
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Patent number: 5620789Abstract: The invention pertains to a composition useful for curing a polyepoxide or advanced epoxy resin consisting essentially of (A) a curing agent capable of reacting with a polyepoxide at elevated temperatures; and (B) boric acid in an amount of from about 0.01 to about 2.0 parts of polyepoxide.Type: GrantFiled: July 26, 1995Date of Patent: April 15, 1997Assignee: The Dow Chemical CompanyInventors: Joseph Gan, James L. Bertram
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Patent number: 5597886Abstract: Heat-curable epoxy resin systems comprising(a) at least one epoxy resin,(b) at least one polycarboxylic acid anhydride, and(c) 1,4-diazabicyclo(2,2,2)octane or a C.sub.1 -C.sub.4 alkyl-substituted derivative of 1,4-diazabicyclo(2,2,2)octane as curing accelerator, and wherein one portion of the curing accelerator (c) is replaced by(d) a complex of a boron halide with an amine, have good reactivity at elevated temperatures and comparatively high stability at temperatures below c. 80.degree. C.Type: GrantFiled: August 7, 1995Date of Patent: January 28, 1997Assignee: Ciba-Geigy CorporationInventors: Roland Moser, Daniel B ar
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Patent number: 5541000Abstract: A thermally-curable aromatic amine-epoxy composition comprises(a) at least one polyepoxy compound;(b) a curing amount of at least one aromatic polyamine compound; and(c) a catalytically effective amount of at least one cure accelerator compound which is a .pi.-electron acceptor, and which lowers the cure exotherm peak temperature (as measured by differential scanning calorimetry (DSC) at 10.degree. C. per minute) of the composition by at least about 8 percent relative to the corresponding composition without the cure accelerator. Such accelerator compounds moderate and/or accelerate the thermal curing of aromatic amine-epoxy resins, enabling cure to occur at lower temperatures and/or in shorter time periods than those required for the unaccelerated composition.Type: GrantFiled: July 1, 1994Date of Patent: July 30, 1996Assignee: Minnesota Mining and Manufacturing CompanyInventors: Leslie C. Hardy, Wendy L. Thompson
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Patent number: 5521261Abstract: Epoxy resin compositions comprising an epoxy resin which is liquid at room temperature and has on average more than one epoxy group per molecule and a quaternary perhydroazepinium salt or a quaternary octahydroazocinium salt as advancement catalyst, when advanced with compounds having two phenolic hydroxyl groups, give excellent products having low viscosity and good viscosity stability, which products can be used, for example, for surface protection, preferably as binder for coatings and paints.Type: GrantFiled: May 27, 1994Date of Patent: May 28, 1996Assignee: Ciba-Geigy CorporationInventors: Arnold Hofer, Hildegard Schneider, Nikolaus Siegenthaler
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Patent number: 5508328Abstract: A curable epoxide composition consists essentially of curable epoxides, dicyandiamide as a curing agent in an amount less than needed to fully cure the epoxides, an imidazole in an amount exceeding that needed as a catalyst and capable of curing the epoxides in combination with the dicyandiamide, a reactivity controller for the imidazole to reduce the curing speed, and a solvent. The use of undesirable solvents such as DMF is reduced. A glass transition temperature greater than 135.degree. C. is obtained in the cured composition and is maximized by balancing the amounts of dicyandiamide, the imidazole, and the reactivity controller.Type: GrantFiled: November 17, 1994Date of Patent: April 16, 1996Assignee: AlliedSignal Inc.Inventor: Larry D. Olson
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Patent number: 5503936Abstract: N-Alkyl-N'-aryl-p-phenylenediamines, when added at 2.5 to 12.5% by weight, based on the total weight of the epoxy resin and hardener, cause the epoxy resin after curing to exhibit substantial increases in physical properties, such as strength, stiffness, toughness and hot/wet properties, compared to the properties of the cured, but unmodified epoxy resin.Type: GrantFiled: January 12, 1995Date of Patent: April 2, 1996Assignee: Ciba-Geigy CorporationInventor: Yefim Blyakhman
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Patent number: 5484873Abstract: Described are novel triethylenediamine adducts of certain 4-hydroxy-substituted, 3,5-hydroxy-substituted and 2,3,4-hydroxy-substituted benzoic acid derivatives, and novel boron trifluoride complexes with cyclic amidines, which are useful for the conversion of thermosettable compositions. Also described are novel thermosettable compositions incorporating the adducts and complexes.Type: GrantFiled: September 14, 1994Date of Patent: January 16, 1996Assignee: Reilly IndustriesInventor: John R. Johnson
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Patent number: 5464910Abstract: An epoxy resin composition having high epoxy curing property and sufficient storage stability, and an epoxy curing agent therefor. The curing agent or the cure accelerating agent obtained by treating the surfaces of (1) an epoxy adduct obtained by adding a nitrogen-containing heterocyclic compound, an aliphatic amine or an aromatic amine to an epoxy compound having one, two or more epoxy groups in one molecule, with (2) a boric acid compound or (3) a boric acid compound and a phenolic compound, exhibits high curing property and storage stability, and can be favorably used as a curing agent for the epoxy resin composition. The epoxy resin composition prepared by mixing the epoxy resin with (1) and (2) or (1) and (3), exhibits excellent curing property and storage stability.Type: GrantFiled: December 22, 1993Date of Patent: November 7, 1995Assignee: Shikoku Chemicals CorporationInventors: Takuo Nakatsuka, Tsuyoshi Toyota, Mie Tanimoto, Akiko Matsumoto
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Patent number: 5439989Abstract: Macrocyclic epoxy resins comprising at least one compound of the formula (I) ##STR1## wherein n is an integer from 3 to 10.R.sup.1 and R.sup.3 are either the same or different and are selected from hydrogen, hydroxyl, alkoxy, allyloxy and epoxypropyloxy (glycidyloxy);R.sup.2 is selected from hydrogen, arylakalkyl optionally substituted with halogen, alkyl optionally substituted with halogen, and aryl optionally substituted with halogen;R.sup.4 is selected from hydrogen, alkyl optionally substituted with halogen, arylalkyl optionally substituted with alkyl or halogen, and aryl optionally substituted with halogen;R.sup.5 is selected from hydrogen, aryl and alkyl; with the proviso that the resin contains on average at least one epoxy group per molecule.Type: GrantFiled: May 3, 1993Date of Patent: August 8, 1995Assignee: Commonwealth Scientific & Industrial Research OrganisationInventors: Trevor C. Morton, Jonathan H. Hodgkin, Buu N. Dao
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Patent number: 5427857Abstract: An improved aqueous cathodic electrocoating composition of an aqueous carrier having dispersed therein a film forming binder of (1) an epoxy resin-amine adduct and (2) a blocked polyisocyanate crosslinking agent; wherein the improvement is the use of a branched epoxy resin to form the adduct which is the reaction product of a polyhydric phenol and a branched epoxy macromonomer formed by the self condensation of an epoxy resin in the presence of a catalyst; the branched epoxy resin has an epoxy equivalent weight of about 700-2,000 and provides an electrocoating composition that has improved throw power and that forms coatings that have improved corrosion resistance in comparison to conventional electrocoating compositions formed from linear epoxy resins.Type: GrantFiled: June 28, 1994Date of Patent: June 27, 1995Assignee: E. I. Du Pont de Nemours and CompanyInventor: Stephen C. Peng
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Patent number: 5426139Abstract: Graft copolymers containing:(1) a phenolic resin; and(2) a poly(alkylene oxide) chain pendant to the phenolic resin,selected such that the graft copolymer has a solubility of no more than about 10 g/L in water, are taught. The graft copolymers are useful in coatings compositions with a curing agent, a solvent, and optionally an epoxy resin. The curable compositions have improved flexibility and/or solvent resistance. They are particularly useful in can coatings.Type: GrantFiled: May 25, 1994Date of Patent: June 20, 1995Assignee: The Dow Chemical CompanyInventors: James L. Bertram, Zeng K. Liao, Lloyd A. McCrary
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Patent number: 5420223Abstract: Described are several preferred acid salts and complexes of N,N-dimethylpyridine (DMAP) and 4-(4-methyl-1-piperidinyl)pyridine (MPP) which are useful as curing agents or as accelerators in preferred epoxy resin curing processes. Also described are particularly preferred processes for forming cured epoxy resin materials which are advantageously employed in large production line scale operations, and curable coating compositions.Type: GrantFiled: October 19, 1993Date of Patent: May 30, 1995Assignee: Reilly Industries, Inc.Inventor: John R. Johnson
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Patent number: 5393806Abstract: An improved liquid matrix system for producing fibre-reinforced plastic components is disclosed. The system comprises (i) a liquid diglycidyl ether of a halogenated bisphenol or a mixture of liquid polyglycidyl ether bisphenols at least one of which being a polyglycidyl ether halogenated bisphenol; and (ii) a curing agent that is a sterically hindered aromatic diamine containing two primary amino groups attached to the carbon atoms in the aromatic nucleus, said carbon atoms not adjacent to each other, and at least one C.sub.1 to C.sub.6 linear or branched alkyl or thioalkyl substituent; the improvement comprising adding to said system a curing accelerator composition containing a mixture of a boron halide and an imidazole unsubstituted or substituted with at least one C.sub.1 to C.sub.6 linear or branched alkyl or C.sub.6 to C.sub.10 aryl.Type: GrantFiled: December 26, 1991Date of Patent: February 28, 1995Assignee: Albemarle CorporationInventor: Farah D. Azarnia
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Patent number: 5391687Abstract: Ultra high molecular weight epoxy resins are produced in a short time by polymerizing a difunctional epoxy resin having two epoxy group per molecule and a dihydric phenol by heating the difunctional epoxy resin and the dihydric phenol which are present in quantities which provide a ratio of phenolic hydroxyl groups to epoxy groups of from 1:0.9 to 1:1.1, in an amide solvent, in the presence of a polymerization catalyst, and the ultra high molecular weight epoxy resins are linearly polymerized so highly as to have the capability of being formed into films having high strength.Type: GrantFiled: October 18, 1993Date of Patent: February 21, 1995Assignee: Hitachi Chemical Company Ltd.Inventors: Katsuji Shibata, Kazuhito Kobayashi, Nozomu Takano, Masami Arai, Ikuo Hoshi