Material Contains A Polyvalent Metal Atom Patents (Class 528/92)
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Patent number: 11965060Abstract: A fluorine-containing epoxy resin for an electronic component represented by the following formula (E) wherein n is an integer of 0 or greater, an average value of n is 0.18 or smaller, and M is a group represented by the following formula (E1), a group represented by the following formula (E2), or a group represented by the following formula (E3) wherein Z is hydrogen or a C2-C10 fluoroalkyl group. The formula (E) being: the formula (E1) being: the formula (E2) being: the formula (E3) being: Also disclosed is a method for producing the fluorine-containing epoxy resin as well as a curable composition containing the fluorine-containing epoxy resin and a curing agent.Type: GrantFiled: November 23, 2021Date of Patent: April 23, 2024Assignee: DAIKIN INDUSTRIES, LTD.Inventors: Yoshito Tanaka, Tomohiro Yoshida
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Patent number: 11667748Abstract: A curable composition of the present invention includes a cationic polymerizable compound; a thermal polymerization initiator; and a storage stabilizer, in which the cationic polymerizable compound includes at least two selected from the group consisting of a glycidyl ether compound, an alicyclic epoxy compound, and an oxetane compound, a content of the thermal polymerization initiator is from 0.3 to 3 parts by mass with respect to 100 parts by mass of the cationic polymerizable compound, and chain curing is enabled by thermal energy generated by a polymerization reaction of the cationic polymerizable compound.Type: GrantFiled: August 29, 2017Date of Patent: June 6, 2023Assignee: MITSUBISHI HEAVY INDUSTRIES, LTD.Inventors: Noriya Hayashi, Toshikatsu Sakakibara, Yusuke Kobayashi, Tatsuya Kimura
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Patent number: 10800888Abstract: The present invention relates to a compound having the following structure I: where Ar1, R, R1, E, m, n, x, y, p, and s are defined herein. The compound of the present invention is useful as an open time additive in waterborne coatings compositions, particularly waterborne paint compositions.Type: GrantFiled: June 25, 2018Date of Patent: October 13, 2020Assignees: Rohm and Haas Company, Dow Global Technologies, LLCInventors: Edward D. Daugs, John J. Rabasco, Antony K. Van Dyk, Tianlan Zhang
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Patent number: 9145334Abstract: An insulated glass sealant includes an elastomeric matrix that is the reaction product of a carboxyl-terminated polymer and a polycarbodiimide. A method of sealing an insulated glass unit includes applying the insulated glass sealant to one or more glass sheets, a spacer to be disposed between the glass sheets, or both; and contacting the one or more glass sheets with the spacer to define an annular space between the glass sheets and to produce the insulated glass unit. The sealants maintain the excellent attributes of traditional polyurethane sealants, such as low water swell, low moisture vapor transmission, good adhesion to the window frame, low migration of the insulating gas, and good workability, but without the use of polyisocyanates in the curing process. Methods for making the sealant and for sealing insulated glass panels, such as glass windows, with these rugged sealants, and the resulting articles, are also provided.Type: GrantFiled: September 22, 2011Date of Patent: September 29, 2015Assignee: Fina Technology, Inc.Inventors: Herbert Shin-I Chao, Nan Tian
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Patent number: 8853350Abstract: The synthesis of a polyoxometalate-loaded epoxy uses a one-step cure by applying an external stimulus to release the acid from the polyoxometalate and thereby catalyze the cure reaction of the epoxy resin. Such polyoxometalate-loaded epoxy composites afford the cured epoxy unique properties imparted by the intrinsic properties of the polyoxometalate. For example, polyoxometalate-loaded epoxy composites can be used as corrosion resistant epoxy coatings, for encapsulation of electronics with improved dielectric properties, and for structural applications with improved mechanical properties.Type: GrantFiled: September 25, 2012Date of Patent: October 7, 2014Assignee: Sandia CorporationInventor: Benjamin J. Anderson
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Patent number: 8618204Abstract: A two-part epoxy-based structural adhesive composition comprising a curable epoxy resin, an amine curing agent, a toughening agent, and an oil-displacing agent. The structural adhesive may optionally include reactive liquid modifiers, fillers, secondary curatives, reactive diluents, surfactants, metal salts, pigments and combinations thereof. The structural adhesive may be used to form bonded joints between adherends having clean surfaces, as well as those having surfaces contaminated with hydrocarbon-containing materials, such as oils, processing aids and lubricating agents.Type: GrantFiled: July 22, 2009Date of Patent: December 31, 2013Assignee: 3M Innovative Properties CompanyInventors: Christopher J. Campbell, Alphonsus V. Pocius, Liya Gorodisher
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Patent number: 8569442Abstract: A hydrogenation process for hydrogenating bisphenol-A-based epoxy resin under low-temperature, low-pressure conditions includes using a hydrogenation reactor that has a gas-distributing agitator functional to introduce and exhaust hydrogen gas and stir liquid reactant, so that hydrogen gas introduced into the hydrogenation reactor can be evenly distributed into a liquid reactant placed into the hydrogenation reactor to make the liquid reactant contain a high level of dissolved hydrogen, which not only enhances activity of an involved hydrogenation catalyst and accelerates hydrogenation reaction, but also allows hydrogenation reaction to be performed in a low-temperature, low-pressure environment. The hydrogenation process improve yield of the hydrogenated bisphenol-A-based epoxy resin to 99.0-99.9%, while significantly reducing building and maintaining costs for the hydrogenation reactor, thus being an economic process.Type: GrantFiled: February 9, 2011Date of Patent: October 29, 2013Assignee: Nan Ya Plastics CorporationInventors: Dein-Run Fung, Jung-Jen Chuang, Chia-Ruey Tsai
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Patent number: 8247484Abstract: A composition comprises a modified polymeric material and a ceramic antiferroelectric particle. The modified polymeric material comprises a high temperature polymer chemically combined with a polar group. A method of making a composition comprises chemically combining a high temperature polymer with a polar group to form a modified polymeric material; and combining the modified polymeric material with antiferroelectric particles to form a composite composition.Type: GrantFiled: June 12, 2008Date of Patent: August 21, 2012Assignee: General Electric CompanyInventors: Daniel Qi Tan, Yang Cao, Patricia Chapman Irwin
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Patent number: 8067481Abstract: The invention provides a low polymerization shrinkage dental composition and a polymerizable dental material selected from the group consisting of wax-like dental material that undergoes ring open polymerization. The dental composition is useful as restorative material and for making artificial teeth, dentures, restoratives, crowns and bridges of high strength dental polymeric material.Type: GrantFiled: September 4, 2008Date of Patent: November 29, 2011Assignee: Dentsply International, Inc.Inventors: Benjamin Jiemin Sun, Andrew Murray Lichkus
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Patent number: 7989530Abstract: A nonlinear composition comprises a polymeric material and at least one ferroelectric, antiferroelectric, or paraelectric particle, wherein the composition has a permittivity greater than or equal to about 5. A method of making a nonlinear composition comprises combining a polymeric material, and at least one ferroelectric, antiferroelectric, or paraelectric particle. The composition has a permittivity greater than or equal to about 5.Type: GrantFiled: July 25, 2008Date of Patent: August 2, 2011Assignee: General Electric CompanyInventors: Daniel Qi Tan, Patricia Chapman Irwin, Yang Cao, Venkat Subramaniam Venkataramani
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Patent number: 7923497Abstract: Disclosed herein is a composition comprising a composition comprising a polymeric material; and a ceramic antiferroelectric particle. Disclosed herein too is a method of tuning a dielectric constant of a composition comprising subjecting a composition comprising a polymeric material and a ceramic antiferroelectric particle to a biasing electric field; and changing the dielectric constant of the composition. Disclosed herein too is a method comprising blending a polymeric material with ceramic antiferroelectric particles to form a composition. Disclosed herein too is a method comprising blending a polymeric material with ceramic antiferroelectric particles to form a composition; applying an electrical field to the composition; and reorienting the ceramic antiferroelectric particles.Type: GrantFiled: November 23, 2005Date of Patent: April 12, 2011Assignee: General Electric CompanyInventors: Daniel Qi Tan, Yang Cao, Patricia Chapman Irwin, Venkat S. Venkataramani
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Publication number: 20100087618Abstract: A linear (meth)acryloyl-containing compound is offered, including a chemical compound having a structure in which structural units expressed by the following general formula (1) (In Formula (1), A is a bivalent hydrocarbon radical which may contain heteroatoms.) are connected by the following general formula (2) or (3) (In Formula (3), R is a hydrogen atom or a methyl group.) (provided that the same substance or different substances may be connected as A of the aforementioned general formula (1)), and the molecular ends are epoxy groups or are expressed by the following general formula (4) (In Formula (4), R is a hydrogen atom or methyl group, and B is a monovalent hydrocarbon radical.), wherein the totality of the structural units expressed by the aforementioned general formula (3) or the aforementioned general formula (4) includes an average of 3 or more in a single molecule, and the number average molecular weight is 500-10,000.Type: ApplicationFiled: September 20, 2006Publication date: April 8, 2010Applicant: DIC CorporationInventors: Seung Taeg Lee, Ren-Hua Jin, Jing Yu, Hongwei He, Dou Luo
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Patent number: 7498085Abstract: An epoxy/silicone mixed resin composition comprising (A?) an organosilicon compound containing at least one aliphatic unsaturated monovalent hydrocarbon group and at least one silicon atom-bonded hydroxyl group, (B) an epoxy resin containing at least one epoxy group, (C) an organohydrogenpolysiloxane, (D) a platinum group metal-based catalyst, and (E) an aluminum-based curing catalyst is used to encapsulate a light-emitting semiconductor member. The light-emitting semiconductor device undergoes little discoloration in a heat test, and has a high emission efficiency, a long life and reduced energy consumption.Type: GrantFiled: November 18, 2004Date of Patent: March 3, 2009Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Tsutomu Kashiwagi, Toshio Shiobara
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Patent number: 7491290Abstract: Disclosed is a two-component adhesive used for electrically and mechanically interconnecting two objects for bonding. The two-component adhesive is made up by first and second adhesive materials separately containing first and second curing agents, respectively. It is only after reaction of the first and second curing agents that the first and second resin components are polymerized. As long as the two adhesive materials are isolated from each other, the adhesive is not cured. In case a metal chelate or a metal alcoholate is used as the first curing agent and a silane coupling agent is used as the second curing agent, cations as a curing component are isolated to cause cationinc polymerization of the first and second resin components to allow for curing at a lower temperature in a shorter time than in case a conventional adhesive is used.Type: GrantFiled: February 14, 2003Date of Patent: February 17, 2009Assignee: Sony Chemical & Information Device CorporationInventors: Takayuki Matsushima, Masao Saito
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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: 7135537Abstract: The present invention is directed to sulfonimide-containing polymers, specifically sulfonimide-containing poly(arylene ether)s and sulfonimide-containing poly(arylene ether sulfone)s, and processes for making the sulfonimide-containing poly(arylene ether)s and sulfonimide-containing poly(arylene ether sulfone)s, for use conductive membranes and fuel cells.Type: GrantFiled: April 28, 2004Date of Patent: November 14, 2006Assignee: E.I. du Pont de Nemours and CompanyInventor: Michael A. Hofmann
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Patent number: 6977274Abstract: The present invention relates to a novel epoxy resin curing system comprising a cationic latent catalytic curing agent containing a hexafluoroantimonate, characterized by exhibiting no shrinkage of volume or inducing an expansion of volume during the curing reaction of the epoxy resin. By the use of the epoxy resin curing system comprising a cationic latent catalytic curing agent containing a hexafluoroantimonate, it is possible to inhibit the shrinkage of volume or to induce the expansion of volume during the curing reaction of the epoxy resin. The development of such curing systems made it possible to improve the dimensional stability and to remove the residual stress, which has caused problems for decades in the production of various molded articles. Furthermore, the curing systems according to the present invention have excellent adhesive properties, thereby making it possible to develop adhesives for accurate spatial infiltration.Type: GrantFiled: January 28, 2000Date of Patent: December 20, 2005Assignee: Korea Research Institute of Chemical TechnologyInventors: Jae-Rock Lee, Soo-Jin Park, Geun Ho Kwak
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Patent number: 6893736Abstract: The present invention provides a thermosetting resin composition useful as a highly filled low CTE underfilling sealant composition which completely fills the underfill space in a semiconductor device, such as a flip chip assembly which includes a semiconductor chip mounted on a carrier substrate, enables the semi-conductor to be securely connected to a circuit board by heat curing and with good productivity, and demonstrates acceptable heat shock properties (or thermal cycle properties). The thermosetting resin composition which is used as an underfilling sealant between such a semiconductor device and a circuit board to which the semiconductor device is electrically connected, includes an epoxy resin component, a latent hardener component, and a polysulfide-based toughening component. The latent hardener component includes a modified amide component and a latent catalyst therefor.Type: GrantFiled: November 15, 2002Date of Patent: May 17, 2005Assignee: Henkel CorporationInventor: Mark M. Konarski
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Patent number: 6881813Abstract: The invention relates to epoxy resin hardener compositions containing at least one mercaptan hardener and at least one metal salt of C8-24 carboxylic acids. These hardeners are distinguished in particular by the fact that catalyzed resins containing epoxy resins and the hardener compositions according to the invention give high-gloss molding compounds, more particularly coatings, after hardening by crosslinking.Type: GrantFiled: January 8, 2003Date of Patent: April 19, 2005Assignee: Cognis Deutschland GmbH & Co. KGInventors: Rainer Hoefer, Ulrich Nagorny
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Patent number: 6864306Abstract: Polymer composites and methods of making the polymer composites are presented. A representative polymer composite includes a polymer resin and a conductive material, wherein the polymer composite is characterized by a dielectric constant greater the 200. A representative method of making the polymer composite can be broadly summarized by the following steps: providing a polymer resin and a conductive material; mixing the polymer resin and the conductive material; and forming the polymer composite, wherein the polymer composite is characterized by a dielectric constant greater than 200.Type: GrantFiled: April 30, 2002Date of Patent: March 8, 2005Assignee: Georgia Tech Research CorporationInventors: Yang Rao, Ching-Ping Wong, Jianwen Xu
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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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Patent number: 6794478Abstract: A process for preparing an epoxy resin involves the reaction of a polyhydric phenol with an epihalohydrin in a water-soluble solvent in the presence of an alkali reactive catalyst wherein a continuous distillation of the reaction product is conducted to (1) isolate a first recovered fraction containing unreacted epihalohydnn, water-soluble solvent and at most 0.01 part by weight of the by-product glycidol per one part by weight of unreacted epihalohydrin; (2) isolate a second recovered fraction containing unreacted epihalohydrin, the by-product glycidol and at most 0.01 part by weight of water-soluble organic solvent per one part by weight of unreacted epihalohydrin; (3) recover the epihalohydrin from the second recovered fraction by washing with water to remove the water-soluble organic solvent and glycidol; and (4) reuse the first recovered fraction and the recovered epihalohydrin from the second recovered fraction as a raw material of the reaction.Type: GrantFiled: September 24, 2002Date of Patent: September 21, 2004Assignee: Dainippon Ink and Chemicals, Inc.Inventors: Ichiro Ogura, Kazuo Arita
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Publication number: 20040063896Abstract: Resin composition comprising an epoxy resin having an epoxide functionality of at least 2.5, a cycloaliphatic epoxy resin, a phenol-formaldehyde novolac and aluminum acetylacetonate. The resin is heat stable and is suitable for fabrication of resin-rich mica tapes having low reactivity at ambient temperatures for good shelf life stability combined with high reactivity above 140° C. for application in press-cured tapes. The dissipation factors at room temperature to at least 200° C. are less than 3.0%.Type: ApplicationFiled: September 30, 2002Publication date: April 1, 2004Inventors: Mark Markovitz, William Gene Newman, Alan Michael Iversen, Mabel S. Yung
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Publication number: 20030149220Abstract: The invention relates to epoxy resin hardener compositions containing at least one mercaptan hardener and at least one metal salt of C8-24 carboxylic acids. These hardeners are distinguished in particular by the fact that catalyzed resins containing epoxy resins and the hardener compositions according to the invention give high-gloss molding compounds, more particularly coatings, after hardening by crosslinking.Type: ApplicationFiled: January 8, 2003Publication date: August 7, 2003Inventors: Rainer Hoefer, Ulrich Nagorny
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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: 6562410Abstract: Heat curable compositions comprising: (A) at least one compound which is capable of undergoing cationic polymerization; (B) at least one quaternary ammonium salt of an aromatic-N-heterocyclic cation and of a non-nucleophilic anion; (C) at least one 1,1,2,2-substituted-1,2-ethane-diol and/or a derivative thereof, and (D) optionally further additives; and wherein said component (C) is a compound of formula (I), wherein each of R1, R2, and R3 independently of the other is unsubstituted phenyl or has one of the meanings of R4; R4 is substituted phenyl optionally substituted &agr;-naphthyl or &bgr;-naphthyl, or an optionally substituted aromatic heterocyclic ring system or each of R1 and R2 and/or R3 and R4 independently of the other form a residue of formula (II), wherein each of R5 and R6 independently of the other is hydrogen or (C1-C4)alkyl; R7 is —(CH2)n— or —S— or —O—; and n is 0, 1, 2, or 3.Type: GrantFiled: March 5, 2001Date of Patent: May 13, 2003Assignee: Vantico Inc.Inventors: Carl Walter Mayer, Ramaswami Sreenivasan, Kikkeri Divakar
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Patent number: 6544651Abstract: The present invention is directed to polymer-ceramic composites having high dielectric constants formed using polymers containing a metal acetylacetonate (acacs) curing catalyst. In particular, it has been discovered that 5 weight percent Co(III) acac can increase the dielectric constant of DER661 epoxy by about 60%. The high dielectric polymers are combined with fillers, preferably ceramic fillers, to form two phase composites having high dielectric constants. Composites having about 30 to about 90% volume ceramic loading and a high dielectric base polymer, preferably epoxy, have been discovered to have a dielectric constants greater than about 60. Composites having dielectric constants greater than about 74 to about 150 are also disclosed. Also disclosed are embedded capacitors with capacitance densities of at least 25 nF/cm2, preferably at least 35 nF/cm2, most preferably 50 nF/cm2. Methods to increase the dielectric constant of the two phase composites having high dielectric constants are also provided.Type: GrantFiled: May 18, 2001Date of Patent: April 8, 2003Assignee: Georgia Tech Research Corp.Inventors: Ching-Ping Wong, Yang Rao
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Publication number: 20030050426Abstract: The present invention relates to degradable polymers having increased functionality, synthesized through ring-opening polymerization of functionalized epoxides alone or in combination with cyclic esters under mild, controlled conditions.Type: ApplicationFiled: June 22, 2001Publication date: March 13, 2003Inventor: Venkatram P. Shastri
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Patent number: 6420320Abstract: The invention is a high molecular weight polyether polyol prepared by the reaction of one or more compounds having one or more active hydrogen compounds with one or more alkylene oxides in the presence of a catalyst comprising calcium having counterions of carbonate and a C6-10 alkanoate in a solvent or dispersant which does not contain active hydrogen atoms. The polyether polyol prepared preferably has an equivalent weight of from about 10,000 to about 30,000, a polydispersity of 1.3 or less and a residual catalyst level of from more than 0 to about 2000 parts per million (ppm). In another embodiment the invention is a process for preparing such high molecular weight polyether polyols. The process comprises first, contacting one or more compounds having one or more active hydrogen atoms with one or more alkylene oxides in the presence of a catalyst. The catalyst comprises calcium having counterions of carbonate and a C6-10 alkanoate in a solvent, wherein the solvent does not contain active hydrogen atoms.Type: GrantFiled: September 7, 2000Date of Patent: July 16, 2002Assignee: The Dow Chemical CompanyInventors: Philip W. McGraw, Robert H. Whitmarsh
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Patent number: 6417316Abstract: Curable epoxy resin compositions, which are obtainable by heating a composition containing at least one epoxy compound, which contains on average at least one, preferably more than one, 1,2-epoxy group and optionally also one or several hydroxyl groups in the molecule, in the presence of at least one Lewis acid as catalyst, wherein the Lewis acid is a salt of trifluoromethanesulfonic acid or of perchloric acid, the counterion of which carries a 2- to 6-fold positive charge, until the epoxy value, measured in equivalent epoxy/kg (Eq/kg) of the starting material, has been reduced by 1 to 60 percent, preferably by 5 to 50 percent; a process for their preparation, and their use for the preparation of fully cured moulded compositions or coatings.Type: GrantFiled: October 19, 1999Date of Patent: July 9, 2002Assignee: Vantico Inc.Inventors: Rolf Wiesendanger, Walter Fischer
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Patent number: 6358877Abstract: Metal cyanide catalysts are complexed with organic sulfone or sulfoxide compounds. The catalysts are active alkylene oxide polymerization catalysts that tend to have short induction periods and moderate exotherms.Type: GrantFiled: May 19, 2000Date of Patent: March 19, 2002Assignee: The Dow Chemical CompanyInventors: Kendra L. Flagler, David E. Laycock
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Patent number: 6335304Abstract: A metal (M) alkyl acid phosphate catalyst for the reaction of an epoxy compound with a carboxyl compound to provide a coating formulation that is stable at room temperature; that is humidity resistant, and non-yellowing, wherein the alkyl acid phosphate has the formula: (RO)n—(P═O)—(OH)m and wherein: a. each R is selected from the group consisting of: i) a C1 to C18 alkly, cycloalkyl, or aryl; ii) a linear or branched C6 to C18 alkyl substituted with —(O—CH2—CH2—)o or —(O—CH—CH3—CH2—)p, wherein o or p is from 1 to 20; iii) a &bgr;-hydroxyethyl compound, R′—X—CH2—CH—OH—CH2—, wherein R′ is a C6 to C18 alkyl or cycloalkyl or aryl, X is either —CH2—, —O— or —COO—; b. n+m=3 and n is between 2 to 1; and c. M is Zn or Sn (II) in a mole equivalent of 0.7 to 1.5 moles per mole of alkyl acid phosphate.Type: GrantFiled: November 9, 1999Date of Patent: January 1, 2002Assignee: KIng Industries, INCInventors: Zhiqiang Alex He, Werner J. Blank, Marie Emmanuelle Picci
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Patent number: 6297344Abstract: A composition comprises from 60-98 weight percent of a casting resin such as an epoxy resin, from 2-30 weight percent of an alcohol or sugar such as 3 (4), 8 (9)-bis(hydroxymethyl)tricyclo[5.2.1.02,6]decane, from 0.2 to 2.0 weight percent of a thermal initiator such as an onium salt, from 0.2-2.0 weight percent of a bonding agent such as 3-glycidyloxypropyltrimethoxysilane, from 0-3.0 weight percent of a flow improver, from 0.2-5.0 weight percent of a metal complex with an organic ligand such as an amino acid, acetate, carbonic acid, amine and acetylacetonate including zinc di-(2-ethylhexanoate) and from 0-4 weight percent of a thixotropic agent and/or a flow modifier.Type: GrantFiled: January 22, 1999Date of Patent: October 2, 2001Assignee: Siemens AktiengesellschaftInventors: Klaus Höhn, Heiner Bayer
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Patent number: 6291077Abstract: A lactone chain-extended polyester polyol of the present invention comprises the reaction product of a lactone and a previously chain-extended phenolic-based hydroxyl compound. The previously chain-extended phenolic-based hydroxyl compound may comprise the reaction product of (i) a lactone or an alkoxylating agent selected from the group consisting of alkylene oxides and alkylene carbonates, and (ii) a phenolic aralkylation polymer comprising the reaction product of a phenolic monomer having at least two free reactive positions; a styrene derivative; and a coupling agent. The previously chain-extended phenolic-based hydroxyl compound also may be chain-extended by reacting with a lactam to produce a lactam chain-extended polyester polyamide. The polyols and polyamides of the present invention provide unique combinations of hard and soft functionalities, which translates into materials exhibiting a unique combination of toughness and hardness.Type: GrantFiled: August 28, 2000Date of Patent: September 18, 2001Assignee: Georgia-Pacific Resins, Inc.Inventors: Rajan Hariharan, David A. Hutchings, Kenneth A. Bourlier, Ellen V. Nagy
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Patent number: 6281154Abstract: Novel compounds having one group 13 element bound with one mono- or di-anionic tridentate ligand, a method of preparation thereof and use thereof as a copolymerization catalyst.Type: GrantFiled: October 28, 1998Date of Patent: August 28, 2001Assignees: Societe de Conseils de Recherches et d'Applications Scientifiques (S.C.R.A.S), Centre National de la Recherche Scientifique (CNRS)Inventors: Guy Bertrand, Jean Bernard Cazaux, Norbert Emig, Régis Reau
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Patent number: 6255434Abstract: The invention is a high molecular weight polyether polyol prepared by the reaction of one or more compounds having one or more active hydrogen compounds with one or more alkylene oxides in the presence of a catalyst comprising calcium having counterions of carbonate and a C6-10 alkanoate in a solvent or dispersant which does not contain active hydrogen atoms. The polyether polyol prepared preferably has an equivalent weight of from about 1000 to about 20,000, a polydispersity of about 1.3 or less and a residual catalyst level of from about 0 to about 2000 parts per million (ppm).Type: GrantFiled: April 27, 1999Date of Patent: July 3, 2001Assignee: The Dow Chemical CompanyInventors: Philip W. McGraw, Robert H. Whitmarsh, Paul E. Cranley, Raymond A. Plepys
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Patent number: 6166151Abstract: A lactone chain-extended polyester polyol of the present invention comprises the reaction product of a lactone and a previously chain-extended phenolic-based hydroxyl compound. The previously chain-extended phenolic-based hydroxyl compound may comprise the reaction product of (i) a lactone or an alkoxylating agent selected from the group consisting of alkylene oxides and alkylene carbonates, and (ii) a phenolic aralkylation polymer comprising the reaction product of a phenolic monomer having at least two free reactive positions; a styrene derivative; and a coupling agent. The previously chain-extended phenolic-based hydroxyl compound also may be chain-extended by reacting with a lactam to produce a lactam chain-extended polyester polyamide. The polyols and polyamides of the present invention provide unique combinations of hard and soft functionalities, which translates into materials exhibiting a unique combination of toughness and hardness.Type: GrantFiled: June 22, 1999Date of Patent: December 26, 2000Assignee: Georgia-Pacific Resins, Inc.Inventors: Rajan Hariharan, David A. Hutchings, Kenneth A. Bourlier, Ellen V. Nagy
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Patent number: 6133383Abstract: A method for preparing a high-heat-resistant-epoxy-resin composition which comprises adding, as catalytic curing agent, a quinoxalinium salt having a benzyl group to difunctional and multifunctional epoxy resin and thermoset resin having a similar structure. The epoxy-resin composition obtained by the present invention is excellent in its impregnating property, processability, impact resistance, drug resistance, electric-insulating property, and adhesiveness.Type: GrantFiled: October 28, 1997Date of Patent: October 17, 2000Assignee: Korea Research Institute of Chemical TechnologyInventors: Jae-Rock Lee, Soo-Jin Park, Sang-Bong Lee
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Patent number: 6133335Abstract: The present invention provides compositions comprising epoxy-containing monomers, where the polymerization of the monomers can be influenced by accelerators. The compositions include at least one photo-polymerizable epoxy monomer and an initiation system. The initiation system comprises at least one organo-iron complex salt and at least one accelerator. The epoxy-containing monomers are energy-polymerized to form useful articles or coated articles.Type: GrantFiled: December 31, 1998Date of Patent: October 17, 2000Assignee: 3M Innovative Properties CompanyInventors: Wayne S. Mahoney, Peggy S. Willett, Michael A. Johnson
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Patent number: 6121405Abstract: A method for preparing a high-heat-resistant-epoxy-resin composition which comprises adding, as catalytic curing agent, a pyrazinium salt having a benzyl group to difunctional and multifunctional epoxy resin and thermoset resin having a similar structure. The epoxy-resin composition obtained by the present invention is excellent in its impregnating property, processability, impact resistance, drug resistance, electric-insulating property, and adhesiveness.Type: GrantFiled: October 29, 1997Date of Patent: September 19, 2000Assignee: Korea Research Institute of Chemical TechnologyInventors: Jae-Rock Lee, Soon-Jin Park, Sang-Bong Lee, Kyu-Wan Lee
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Patent number: 6096836Abstract: Disclosed herein is a curing catalyst comprising at least one compound which is a substituted or unsubstituted aromatic or heteroaromatic compound and having any one of groups (I) --O--R.sub.1, (II) --O--CY--R.sub.1, or (III) --O--CY--X--R.sub.1, the groups being directly bonded to the armoatic or heteroaromatic ring, in a number of 1 to 10 wherein R.sub.1 may be the same or different and is a substituted or unsubstituted hydrocarbon group having 1 to 20 carbon atoms, X is O or NH and Y is O or S. Furthermore, an epoxy resin composition comprising the curing catalyst is disclosed.Type: GrantFiled: March 2, 1998Date of Patent: August 1, 2000Assignee: Kabushiki Kaisha ToshibaInventors: Shuzi Hayase, Yoshihiko Nakano, Shinji Murai, Yukihiro Mikogami
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Patent number: 6034185Abstract: This invention relates to an epoxy resin composition which comprises polyalkyl phenol resins or polyalkyl phenol epoxy resins or both, wherein the polyalkyl phenol resins are represented by formula (I): ##STR1## wherein Ra, Rb and Rc may be the same or different from each other and stand for C.sub.1-5 alkyl styryl or halogen respectively;n is an integer of 0 to 4;k is an integer of 0 to 3;l is an integer of 0 to 4; andm is an integer of 1 to 10;and the polyalkyl phenol epoxy resins, which are obtained by reacting polyalkyl phenol resins of formula (I) with epihalohydrins, are represented by formula (II): ##STR2## wherein G stands for ##STR3## while the other symbols are the same as those defined above. The epoxy resin composition of this invention is able to provide a reactivity at lower temperatures and provide lower viscosity when used as hardener resins, as compared with traditional phenolic novolacs.Type: GrantFiled: October 6, 1997Date of Patent: March 7, 2000Assignee: Chang Chun Plastics Co., Ltd.Inventors: Kuen-Yuan Hwang, Hong-Hsing Chen, Biing Lu Perng, Shang Wen Chen
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Patent number: 6031012Abstract: Provided is a curable composition comprising (A) a phenolic compound having a carbon-carbon double bond, (B) a compound having an SiH group, and (C) a foaming agent. The composition can be foamed and cured at room temperature or under heat at relatively low temperatures, and is poorly corrodable and poorly toxic.Type: GrantFiled: October 27, 1998Date of Patent: February 29, 2000Assignee: Kaneka CorporationInventors: Naoaki Nakanishi, Koji Himeno, Shintaro Komitsu
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Patent number: 6005063Abstract: Process for the preparation of compound of the formula: ##STR1## wherein R.sub.c represents a residue comprising one or more additional groups of the formula: ##STR2## by heating a compound of the formula (A) ##STR3## at a temperature in the range of from 120 to 220.degree. C. in the presence of hydrogen halide addition salt of tertiary amine;process for the preparation of epoxy compounds starting from the reaction of a polyphenol compound and glycidol; andepoxy resins obtained by this process showing a significantly lower content of intermingled clorine and being substantially free of usual build-up products.Type: GrantFiled: February 6, 1998Date of Patent: December 21, 1999Assignee: Shell Oil CompanyInventors: Johannes Adrianus Van Doorn, Jozef Jacobus Titus Smits, Eric Johannes Vos
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Patent number: 5998568Abstract: A method for making a polyester resin comprises reacting a first polyfunctional alcohol or polyfunctional thiol and a carbonate in the presence of a catalyst to form an alkoxylated intermediate. The catalyst comprises: (1) a metal, a salt of a metal, or mixtures thereof and (2) a quaternary ammonium salt, a tertiary amine, an imidazole, or mixtures thereof. The alkoxylated intermediate is then reacted with a polyfunctional organic acid or anhydride thereof to form the polyester resin.Type: GrantFiled: January 14, 1999Date of Patent: December 7, 1999Assignee: Reichhold, Inc.Inventors: Hildeberto Nava, Karin F. Nelson-Baron
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Patent number: 5969059Abstract: An impregnation resin composition comprising an alicyclic epoxy compound, an acid anhydride, an aluminum compound having an organic group, and butylglycidyl ether, wherein the alicyclic epoxy compound contains not more than 30 ppm in concentration of Na ion component.Type: GrantFiled: March 13, 1998Date of Patent: October 19, 1999Assignee: Kabushiki Kaisha ToshibaInventors: Shinji Murai, Shuji Hayase
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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: 5908912Abstract: An electrodepositable coating composition is provided comprising (a) an active hydrogen-containing, cationic salt group-containing resin electrodepositable on a cathode; (b) a curing agent for transurethanation, transamidation or transesterification curing like at least a partially capped polyisocyanate curing agent; and (c) a catalytic mixture of bismuth and an amino acid or amino acid precursor. Optionally, an auxiliary acid may be present to increase the effectiveness of the amino acid in the mixture with bismuth.Type: GrantFiled: June 3, 1997Date of Patent: June 1, 1999Assignee: PPG Industries Ohio, Inc.Inventors: Raphael O. Kollah, Matthew S. Scott, Gregory J. McCollum, Joseph A. Bethoski
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Patent number: 5856415Abstract: A method for producing a metal-containing transparent polymer by the reaction of a metal carboxylate, with a clear setting resin system comprising a thermosetting resin and a curing agent. The reaction occurs in a temperature in the range of from about 0.degree. to about 100.degree. C. under conditions which prevent air from being entrapped in the mixture, either during mixing of the reagents or during reaction. The metal carboxylate contains from about 20 to about 60 weight percent of metal. The reagents react for a time sufficient to form a transparent polymer. The resins include preferably epoxies, polyesters, polyurethane, polyisocyanurate, polyether sulfones, polyimides, and mixtures of two or more of these thermoset polymers. The final metal-containing transparent polymer preferably contains at least 15% by weight of the metal. Preferred metals include antimony, barium, bismuth, cadmium, cerium, cobalt, copper, iron, lead, molybdenum, tungsten, ranadium, and zirconium.Type: GrantFiled: August 28, 1997Date of Patent: January 5, 1999Assignee: Bar-Ray Products, Inc.Inventors: Arthur Lagace, Ray C. Lapof
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Patent number: 5844070Abstract: A process for activating double metal cyanide catalysts is disclosed. A polyol starter or starter/catalyst mixture is heated under vacuum under conditions effective to achieve improved stripping compared with that which can be achieved through conventional vacuum stripping. Coupling vacuum stripping with inert gas sparging or stripping in the presence of an organic solvent gives a starter/catalyst mixture that activates rapidly in an epoxide polymerization process. Rapid activation makes process start-ups reliable and reduces cycle time. The process gives polyols with lower viscosity, lower polydispersity, and lower unsaturation for better polyurethanes.Type: GrantFiled: May 16, 1997Date of Patent: December 1, 1998Assignee: Arco Chemical Technology, L.P.Inventors: John E. Hayes, Leah J. Langsdorf, Bruce H. Isaacs, Fred J. Armellini