Phenolic Reactant Contains A Heterocyclic Group Other Than A 1,2-epoxy Group Per Se Patents (Class 528/96)
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Patent number: 12043697Abstract: An epoxy resin composition and a cured product thereof are provided, the epoxy resin composition comprising an epoxy resin (A), a curing agent (B) comprising a compound represented by the following formula (B-1) (wherein R1 represents a hydrogen atom, a halogen atom, a methoxy group or a hydrocarbon group having 1 to 12 carbon atoms), and an imidazole adduct-type curing accelerator (C), wherein the molar ratio of the content of a phenolic hydroxide group to the content of an epoxy group in the epoxy resin composition is 0.25 to 0.67.Type: GrantFiled: October 16, 2019Date of Patent: July 23, 2024Assignee: SUMITOMO CHEMICAL COMPANY, LIMITEDInventors: Hirofumi Kato, Kenichi Takeuchi
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Patent number: 11807750Abstract: Thermoset bulk molding compounds (BMC) useful for making electrically conductive components such as bipolar plates for fuel cells are described. The thermoset bulk molding compounds incorporate graphene nanoplatelets to increase the through-plane electrical conductivity by at least 20% compared to BMCs without the graphene nanoplatelets. Additionally, these compositions have low shrinkage, low density for lightweight parts, and are easily processed. The compositions can be used to prepare a variety of electrically conductive components, including bipolar plates for fuel cells and chemical storage batteries that operate at temperatures of less than 100° C.Type: GrantFiled: July 6, 2021Date of Patent: November 7, 2023Assignee: LyondellBasell Advanced Polymers Inc.Inventors: John E. Stroh, Jody D. Riddle
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Patent number: 11701922Abstract: A metallic or metallized reinforcer has at least a surface of which is at least partially metallic, the at least partially metallic surface being coated with a polybenzoxazine sulfide whose repeating units include at least one unit corresponding to formula (I) or (II): in which the two oxazine rings are connected together via a central aromatic group, the benzene ring of which bears one, two, three or four groups of formula —Sx—R in which “x” is an integer from 1 to 8 and R represents hydrogen or a hydrocarbon-based group including 1 to 10 carbon atoms and optionally a heteroatom chosen from O, S, N and P. Such a reinforcement can be used for the reinforcement of a rubber article, in particular a motor vehicle tire.Type: GrantFiled: June 12, 2018Date of Patent: July 18, 2023Assignee: COMPAGNIE GENERALE DES ETABLISSEMENTS MICHELINInventors: Milan Fedurco, Marco Ribezzo
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Patent number: 10125116Abstract: Described herein are compounds, and pharmaceutically acceptable salts and prodrugs thereof, which are useful as inhibitors of IMPDH. In certain embodiments, a compound of the invention selectively inhibits a parasitic IMPDH versus a host IMPDH. Further, the invention provides pharmaceutical compositions comprising one or more compounds of the invention. The invention also relates to methods of treating various parasitic and bacterial infections in mammals. Moreover, the compounds may be used alone or in combination with other therapeutic or prophylactic agents, such as anti-virals, anti-inflammatory agents, antimicrobials and immunosuppressants.Type: GrantFiled: December 16, 2014Date of Patent: November 13, 2018Assignees: Brandeis University, University of Georgia Research Foundation, Inc., The Brigham and Women's Hospital, Inc.Inventors: Lizbeth K. Hedstrom, Gregory D. Cuny, Deviprasad R. Gollapalli, Sivapriya Kirubakaran, Sushil K. Maurya, Boris Striepen, Suresh K. Gorla, Corey R. Johnson, Mandapati Kavitha, Jihan Khan
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Patent number: 9790330Abstract: A method for forming a conjugated heteroaromatic polymer is described, wherein at least one compound of formula (1) is polymerized using an acid as a catalyst, wherein X is selected from S, O, Se, Te, PR2 and NR2, Y is hydrogen (H) or a precursor of a good leaving group Y? whose conjugate acid (HY) has a pKa of less than 30, Z is hydrogen (H), silyl, or a good leaving group whose conjugate acid (HZ) has a pKa of less than 30, b is 0, 1 or 2, each R1 is a substituent, and the at least one compound of formula (1) being polymerized includes at least one compound of formula (1) with Z=H and Y?H.Type: GrantFiled: October 28, 2012Date of Patent: October 17, 2017Assignee: PolyM technology corporationInventors: Chien-Chung Han, Balasubramanian Arumugam
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Patent number: 8999510Abstract: A metal-clad phenolic resin laminate obtained by heating and pressing a lamination which comprises: (i) a central layered portion comprising one paper base prepreg which is made of a paper base impregnated with a first phenolic resin composition containing a resol-based resin, or a predetermined number of the paper base prepregs laid on each other; (ii) outer layered portions laid on an upper and a lower sides of the central layered portion, in which each of the outer layered portions comprises one glass fiber substrate prepreg which is made of a glass fiber substrate impregnated with a second phenolic resin composition containing a resol-based resin, or a predetermined number of the glass fiber substrate prepregs laid on each other; and (iii) a metal foil laid at least on one of the outer layered portions laid on the upper and lower sides of the central layered portion.Type: GrantFiled: September 28, 2009Date of Patent: April 7, 2015Assignee: Sumitomo Bakelite Company, Ltd.Inventor: Masao Uesaka
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Patent number: 8981038Abstract: A polyimide including a structure shown as Formula II is provided, wherein X is halogen, A1 is selected from one of Formula 1 to Formula 18, and n is from 2 to 500,Type: GrantFiled: December 25, 2012Date of Patent: March 17, 2015Assignee: Taiwan Textile Research InstituteInventors: Der-Jang Liaw, Wen-Hsiang Chen, Ying-Chi Huang, Bo-Cheng Tao
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Publication number: 20150045528Abstract: Novel oligomers and polymers derived from the reaction of benzoxazine compounds with a mixture of epoxy compounds and amine compounds are disclosed. The compositions are useful in coating, sealants, adhesive and many other applications.Type: ApplicationFiled: October 25, 2012Publication date: February 12, 2015Inventors: Ilya Gorodisher, Dmitriy Salnikov, Mary M. Caruso
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Patent number: 8703882Abstract: Phosphorus-containing benzoxazine-based bisphenols and derivatives thereof are disclosed. The phosphorus-containing benzoxazine-based bisphenols are prepared by reacting DOPO with benzoxazine to form the phosphorus-containing benzoxazine-based bisphenols. The phosphorus-containing benzoxazine-based bisphenols can further to form advanced epoxy resins. The advanced epoxy resins can further be cured to form flame retardant epoxy thermosets.Type: GrantFiled: December 28, 2010Date of Patent: April 22, 2014Assignee: National Chunghsing UniversityInventors: Ching-Hsuan Lin, Hung-Tse Lin, Sheng Lung Chang, Yu-Ming Hu
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Publication number: 20140010983Abstract: A curable composition includes 3-substituted benzoxazine, polyepoxide, and polythiol. Articles including the curable composition, methods of curing the curable composition, and a tack-free reaction product preparable from the curable composition are also disclosed.Type: ApplicationFiled: March 27, 2012Publication date: January 9, 2014Applicant: 3M INNOVATIVE PROPERTIES COMPANYInventor: Ilya Gorodisher
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Patent number: 8609806Abstract: To provide phosphorus-containing epoxy resins and phosphorus-containing epoxy resin compositions having high levels of appearance, yield and economic efficiency and cured products thereof that are used for various applications. A phosphorus-containing phenol compound represented by Formula (3) obtained by reacting a compound represented by Formula (2) with a compound represented by Formula (1), wherein in the peak area (A) of the component represented by Formula (1) on a chromatogram measured under specific conditions by gel permeation chromatography, peak area (B) on the high-molecular-weight side of the component of Formula (1), and total area (C) of peak area (A) and peak area (B), the value obtained by dividing peak area (B) by total area (C) is 8 area % or less, and epoxy resin compositions and cured products comprising the phosphorus-containing phenol compound as an essential ingredient.Type: GrantFiled: September 2, 2009Date of Patent: December 17, 2013Assignee: Nippon Steel & Sumikin Chemical Co., Ltd.Inventors: Tetsuya Nakanishi, Hideyasu Asakage, Seigo Takuwa
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Publication number: 20130052381Abstract: This disclosure relates to epoxides, polyepoxide compositions and epoxy resins whose degradation products exhibit little or no estradiol binding activity. Also disclosed are methods for making the disclosed compositions and articles of manufacture comprising the disclosed compositions.Type: ApplicationFiled: August 1, 2012Publication date: February 28, 2013Inventors: Robert R. Gallucci, James A. Mahood, Jean Francois Morizur, Steve Dimond
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Patent number: 8263714Abstract: An epoxy resin composition including an epoxy resin and a curing agent as essential components, in which the curing agent comprises a phenol resin which has each structural moiety of a phenolic hydroxyl group-containing aromatic hydrocarbon group (P), an alkoxy group-containing aromatic hydrocarbon group (B) and a divalent aralkyl group (X), and also has, in a molecular structure, a structure in which the phenolic hydroxyl group-containing aromatic hydrocarbon group (P) and the alkoxy group-containing aromatic hydrocarbon group (B) are bonded with the other phenolic hydroxyl group-containing aromatic hydrocarbon group (P) or alkoxy group-containing aromatic hydrocarbon group (B) via the divalent aralkyl group (X).Type: GrantFiled: June 10, 2011Date of Patent: September 11, 2012Assignee: Dainippon Ink and Chemicals, Inc.Inventors: Ichiro Ogura, Yoshiyuki Takahashi, Kazuo Arita, Kunihiro Morinaga, Yutaka Satou
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Publication number: 20120165429Abstract: The present application relates to a method for preparing epoxy resins from a mixture of epoxidized phenolic compounds, wherein said epoxidized phenolic compounds are obtained by the epoxidation of natural phenolic compounds selected from the group comprising simple phenol, acid-phenol, coumarin, naphthoquinone, stillbenoid, flavonoid, isoflavanoid, anthocyanin, condensed tannin and hydrolyzable tannin.Type: ApplicationFiled: May 27, 2010Publication date: June 28, 2012Applicant: Centre National De La Recherche Scientifique (C.N.R.S.)Inventors: Bernard Boutevin, Sylvain Caillol, Carine Burguiere, Sylvie Rapior, Hélène Fulcrand, Hélène Nouailhas
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Patent number: 7985822Abstract: An epoxy resin composition including an epoxy resin and a curing agent as essential components, in which the curing agent comprises a phenol resin which has each structural moiety of a phenolic hydroxyl group-containing aromatic hydrocarbon group (P), an alkoxy group-containing aromatic hydrocarbon group (B) and a divalent aralkyl group (X), and also has, in a molecular structure, a structure in which the phenolic hydroxyl group-containing aromatic hydrocarbon group (P) and the alkoxy group-containing aromatic hydrocarbon group (B) are bonded with the other phenolic hydroxyl group-containing aromatic hydrocarbon group (P) or alkoxy group-containing aromatic hydrocarbon group (B) via the divalent aralkyl group (X).Type: GrantFiled: August 31, 2005Date of Patent: July 26, 2011Assignee: Dainippon Ink and Chemicals, Inc.Inventors: Ichiro Ogura, Yoshiyuki Takahashi, Kazuo Arita, Kunihiro Morinaga, Yutaka Satou
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Patent number: 7888397Abstract: A poly(phenylene) compound of copolymers that can be prepared with either random or multiblock structures where a first polymer has a repeat unit with a structure of four sequentially connected phenyl rings with a total of 2 pendant phenyl groups and 4 pendant tolyl groups and the second polymer has a repeat unit with a structure of four sequentially connected phenyl rings with a total of 6 pendant phenyl groups. The second polymer has chemical groups attached to some of the pendant phenyl groups selected from CH3, CH2Br, and CH2N(CH3)3Br groups. When at least one group is CH2N(CH3)3Br, the material functions as an anion exchange membrane.Type: GrantFiled: April 30, 2008Date of Patent: February 15, 2011Assignee: Sandia CorporationInventors: Michael Hibbs, Christopher J. Cornelius, Cy H. Fujimoto
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Patent number: 7763700Abstract: An epoxy resin curing composition containing a compound having a benzoxazole structure represented by formula (I): wherein X1 and X2, which may be the same or different, each represent hydrogen, a substituent having a phenolic hydroxyl group, or a substituent having an epoxy group, provided that X1=X2?H; or X1 and X2 are taken together to form a 3- to 8-membered, saturated or unsaturated heterocyclic ring substituted with a substituent having a phenolic hydroxyl group or a substituent having an epoxy group; Y1 represents oxygen or sulfur; Z1 represents a substituted or unsubstituted C1-C8 hydrocarbon group or a substituted or unsubstituted C1-C8 alkoxy group; m is an integer of 0 to 4; when m is 2 to 4, a plurality of Z1s may be the same or different; n is an integer of 0 to 2; and A1 represents hydrogen, a substituent having a phenolic hydroxyl group or a substituent having an epoxy group.Type: GrantFiled: March 14, 2007Date of Patent: July 27, 2010Assignee: Adeka CorporationInventor: Takahiro Mori
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Patent number: 7632626Abstract: There is provided an anti-reflective coating forming composition for lithography comprising a polymer having an ethylenedicarbonyl structure and a solvent; an anti-reflective coating formed from the composition; and a method for forming photoresist pattern by use of the composition. The anti-reflective coating obtained from the composition can be used in lithography process for manufacturing a semiconductor device, has a high preventive effect for reflected light, causes no intermixing with photoresists, and has a higher etching rate than photoresists.Type: GrantFiled: April 13, 2006Date of Patent: December 15, 2009Assignee: Nissan Chemical Industries, Ltd.Inventor: Rikimaru Sakamoto
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Publication number: 20090253887Abstract: An epoxy resin curing composition containing a compound having a benzoxazole structure represented by formula (I): wherein X1 and X2, which may be the same or different, each represent hydrogen, a substituent having a phenolic hydroxyl group, or a substituent having an epoxy group, provided that X1?X2?H; or X1 and X2 are taken together to form a 3- to 8-membered, saturated or unsaturated heterocyclic ring substituted with a substituent having a phenolic hydroxyl group or a substituent having an epoxy group; Y1 represents oxygen or sulfur; Z1 represents a substituted or unsubstituted C1-C8 hydrocarbon group or a substituted or unsubstituted C1-C8 alkoxy group; m is an integer of 0 to 4; when m is 2 to 4, a plurality of Z1s may be the same or different; n is an integer of 0 to 2; and A1 represents hydrogen, a substituent having a phenolic hydroxyl group or a substituent having an epoxy group.Type: ApplicationFiled: March 14, 2007Publication date: October 8, 2009Applicant: ADEKA CORPORATIONInventor: Takahiro Mori
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Patent number: 7150902Abstract: Articles are coated by applying a coating composition of a high Tg phenoxy-type material having a Tg of at least about 75° C. to at least a portion of a surface of an article, and forming a dried/cured coating of the high Tg phenoxy-type material on the article surface, where the coating has the high Tg phenoxy-type material and a PHAE; or the article surface comprises a coating includes a PHAE; or the coating has the high Tg phenoxy-type material and a PHAE, and the article surface includes a coating layer of a PHAE.Type: GrantFiled: April 7, 2004Date of Patent: December 19, 2006Assignee: Pepsico, Inc.Inventor: Said Farha
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Patent number: 6903180Abstract: This invention relates to novel epoxy resins and epoxy resin compositions comprising said epoxy resins or cured articles thereof. The cured articles have excellent properties in respect to flame retardance, adhesiveness, moisture resistance and heat resistance and can be used in applications such as lamination, molding, casting and adhesion. The epoxy resins of this invention are represented by the following formula (3) wherein Y1 denotes a glycidyloxyarylmethyl group represented by —CH2—Ar—OG, Y2 and Y3 denote independently a glycidyl group or the aforementioned glycidyloxyarylmethyl group, Ar denotes a phenylene group which can be substituted with up to two hydrocarbon groups and G denotes a glycidyl group.Type: GrantFiled: December 10, 2001Date of Patent: June 7, 2005Assignee: Nippon Steel Chemical Co., Ltd.Inventors: Masashi Kaji, Koichiro Ogami
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Publication number: 20040158023Abstract: A halogen-free resin composition is provided, comprising: (A) one or more phosphorous-containing epoxy resins; (B) a hardener; and (C) a hardening accelerator, wherein the hardener of component (B) has the structure represented by the following formula (I): 1Type: ApplicationFiled: August 4, 2003Publication date: August 12, 2004Inventors: Kuen-Yuan Hwang, An-Pang Tu, Chi-Yi Ju, Wen-Tsai Tsai
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Publication number: 20040068082Abstract: The present invention relates to poly(arylene ethers) used as low k dielectric layers in electronic applications and articles containing such poly(arylene ethers) comprising the structure: 1Type: ApplicationFiled: October 1, 2002Publication date: April 8, 2004Applicant: Chartered Semiconductor Manufacturing Ltd.Inventors: Christopher Lim, Siu Choon Ng, Hardy Chan, Simon Chooi, Mei Sheng Zhou
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Publication number: 20040054120Abstract: Compounds of formula (I) or (II), wherein R1 is C1-C18alkyl; C5-C12cycloalkyl that is unsubstituted or substituted by one or more C1-C6alkyl groups or C1-C22alkoxy groups; C5-C22aryl that is unsubstituted or substituted by one or more C1-C6alkyl groups or C1-C6alkoxy groups; or C7-C30aralkyl that is unsubstituted or substituted by one or more C1-C6alkyl groups or C1-C6alkoxy groups, and the radicals R2 to R13 are each independently of the others hydrogen; —NO2; dialkylamino; alkylthio; alkylsulfonyl; halogen; C1-C18alkyl; C1-C18alkoxy; C1-C18alkoxyalkyl; C5-C12cycloalkyl that is unsubstituted or substituted by one or more C1-C6alkyl groups or C1-C6alkoxy groups; C5-C22aryl that is unsubstituted or substituted by one or more C1-C6alkyl groups or C1-C6alkoxy groups; or C7-C10alkyl that is unsubstituted or substituted by one or more C1-C6alkyl groups or C1-C6alkoxy groups, are suitable as flame-proofing agents for thermoplastic or thermosetting polymers.Type: ApplicationFiled: July 21, 2003Publication date: March 18, 2004Inventors: Franck Magendie, Ulrich Weidmann
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Patent number: 6551714Abstract: The present invention provides a resin composition having excellent flame retardancy without using any halogen-containing flame retardant, and prepregs and laminates using such a resin composition. More specifically, the present invention provides a flame-retardant resin composition comprising as essential components (A) an epoxy resin, (B) a curing agent and (C) a phosphorus compound containing at least as part thereof a phosphine oxide compound, a prepreg produced by impregnating this flame-retardant resin composition in a fiber base, and a laminate produced by hot-pressing a single sheet or a pile of two or more sheets of the prepreg.Type: GrantFiled: August 21, 2000Date of Patent: April 22, 2003Assignee: Sumitomo Bakelite Company LimitedInventor: Akihiko Tobisawa
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Process for manufacturing a hydroxyester derivative intermediate and epoxy resins prepared therefrom
Patent number: 6534621Abstract: A process for manufacturing an &agr;-halohydrin intermediate and an epoxy resin prepared therefrom including epoxidizing an &agr;-halohydrin intermediate produced from an in situ halide substitution-deesterification of an &agr;-hydroxy ester derivative which has been obtained by the coupling reaction of a phenol or a mixture of phenols and a glycidyl ester optionally in the presence of a catalyst.Type: GrantFiled: May 9, 2001Date of Patent: March 18, 2003Assignee: Dow Global Technologies Inc.Inventors: Clinton J. Boriack, Zeng K. Liao -
Publication number: 20020161135Abstract: The invention pertains to a coating composition comprising a first compound comprising at least one bicyclo- or spiro-orthoester group and a second compound comprising at least two hydroxyl-reactive groups. The invention also comprises a process for curing the present coating composition. More particularly, the latent hydroxyl groups of the bicyclo- or spiro-orthoester groups have to be deblocked and reacted with the hydroxyl-reactive groups of the second compound if the present coating composition is to be cured. Further, a process for making bicyclo-orthoester compounds from the corresponding oxetane compound is described, as are polymers comprising at least one bicyclo- or spiro-orthoester group.Type: ApplicationFiled: August 22, 2001Publication date: October 31, 2002Inventors: Keimpe Jan van den Berg, Klaus Hobel, Huig Klinkenberg, Arie Noomen, Josephus Christiaan van Oorschot
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Patent number: 6462106Abstract: Disclosed is a novel amino-polyether-modified epoxy for an electrodeposition paint. The amin-polyether-modified epoxy compound is obtained by reacting amino polyether represented by a formula as follow: wherein m is an integer of 5 or more, R is hydrogen, methyl group or ethyl group, and n is 2 or 3, with polyglycidyl ether having a molecular weight of 1,000 to 7,000 and an epoxy equivalent of 500 to 3,500, wherein an equivalent ratio of a primary amino group of the amino polyether to an epoxy group of the polyglycidyl ether is controlled within the range of 0.52 to 1.0.Type: GrantFiled: January 25, 2001Date of Patent: October 8, 2002Assignee: Nippon Paint Co., Ltd.Inventors: Shinsuke Shirakawa, Mitsuo Yamada
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Publication number: 20020010305Abstract: Process for the production of 2,2,6-trimethylcyclohexane-1,4-dione by epoxidation of &bgr;-isophorone with organic percarboxylic acids at a water content below 5 wt.-% and subsequent isomerization of the mixture of &bgr;-isophorone epoxide and hydroxyisophorone.Type: ApplicationFiled: May 8, 2001Publication date: January 24, 2002Inventors: Steffen Krill, Klaus Huthmacher, Sylvain Perrin
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Publication number: 20010031851Abstract: The object was to provide an epoxy resin composition which has excellent flame retardancy, heat resistance and humidity resistance and is advantageously used for semiconductor encapsulating, laminated boards, electrical insulation and the like.Type: ApplicationFiled: February 15, 2001Publication date: October 18, 2001Inventors: Takao Fukuzawa, Takayoshi Hirai, Tetsuro Imura, Yoshinobu Ohnuma
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Patent number: 6303672Abstract: A self-dispersing curable epoxy composition is prepared upon contacting an epoxy resin with a polyoxyalkylenemonoamine having a molecular weight of from about 3,000 to about 15,000 in a ratio of about 0.001 to 0.060 reactive equivalents of polyoxyalkylenemonoamine to about 1.0 reactive equivalents of epoxy resin. The self-dispersing curable epoxy resin forms an aqueous dispersion upon mixing with water. When cured, the dispersion is useful as a coating composition.Type: GrantFiled: June 7, 1995Date of Patent: October 16, 2001Assignee: Henkel CorporationInventors: John G. Papalos, Shailesh Shah, Reuben H. Grinstein, Joseph L. Mulvey, Brian G. Jewell
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Patent number: 6297329Abstract: The invention pertains to a coating composition comprising a first compound comprising at least one bicyclo- or spiro-orthoester group and a second compound comprising at least two hydroxyl-reactive groups. The invention also comprises a process for curing the present coating composition. More particularly, the latent hydroxyl groups of the bicyclo- or spiro-orthoester groups have to be deblocked and reacted with the hydroxyl-reactive groups of the second compound if the present coating composition is to be cured. Further, a process for making bicyclo-orthoester compounds from the corresponding oxetane compound is described, as are polymers comprising at least one bicyclo- or spiro-orthoester group.Type: GrantFiled: February 21, 1997Date of Patent: October 2, 2001Assignee: Akzo Nobel NVInventors: Keimpe Jan van den Berg, Klaus Hobel, Huig Klinkenberg, Arie Noomen, Josephus Christiaan van Oorschot
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Patent number: 6294596Abstract: A self-dispersing curable epoxy composition is prepared upon contacting an epoxy resin with a polyoxyalkyleneamine having a molecular weight of from about 3,000 to about 15,000 in a ratio of about 0.001 to 0.060 reactive equivalents of polyoxyalkyleneamine to about 1.0 reactive equivalents of epoxy resin. The self-dispersing curable epoxy resin forms an aqueous dispersion upon mixing with water. When cured, the dispersion is useful as a coating composition.Type: GrantFiled: September 15, 1995Date of Patent: September 25, 2001Assignee: Henkel CorporationInventors: John G. Papalos, Shailesh Shah, Reuben H. Grinstein, Joseph L. Mulvey, Brian G. Jewell
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Patent number: 6291621Abstract: Provided are novel, electropolymerizable monomers of the formulae: wherein R1, R2 and R3 are selected from the group consisting of —H, —O(CH2)nCH3, wherein n has a value of 0 to 11 and m has a value of 1 to 4, and wherein no more than one of R2 and R3 is —H. Also provided are polymers resulting from the electropolymerization of these monomers.Type: GrantFiled: February 23, 1999Date of Patent: September 18, 2001Assignee: The United States of America as represented by the Secretary of the Air ForceInventors: Loon-Seng Tan, Balasubramanian Sankaran
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Patent number: 6051294Abstract: Hydroxy-functional polyethers having a "cardo" diphenylene group in their backbones are prepared by contacting at least one dinucleophilic monomer with at least one dtglycidyl ether of a cardo bisphenol, such as bis(hydroxyphenyl)fluorene, phenolphthalein, or phenolphthalimidine or a substituted cardo bisphenol, such as a substituted bis(hydroxyphenyl)fluorene, a substituted phenolphthalein or a substituted phenolphthalimidine, under conditions sufficient to cause the nucleophillo moieties of the dinucleophilic monomer to react with epoxy moieties to form a polymer backbone containing pendant hydroxy moieties and ether, imino, amino, sulfonamido or ester linkages. These polyethers possess a combination of high barrier to oxygen transmission (i.e., oxygen transmission rate less than 10.0 cm.sup.3 -mil/100 in.sup.2 -atm-day to oxygen) and high heat resistance (i.e., Tg above 120.degree. C.).Type: GrantFiled: February 9, 1998Date of Patent: April 18, 2000Assignee: The Dow Chemical CompanyInventors: Jerry E. White, H. Craig Silvis, Stephen E. Bales, Michael N. Mang, Muthiah N. Inbasekaran
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Patent number: 6037425Abstract: The present invention provides an epoxy resin composition useful for casting applications, comprising a reaction product obtained by reacting (A) a bisphenol epoxy resin, and (B) bisphenol compounds, and if necessary, (C) monofunctional phenols or carboxylic acid compounds, in the presence of sodium compounds, wherein the epoxy resin composition has(a) an epoxy equivalent: 250 to 500 g/equivalent,(b) a sodium content: 20 to 200 ppm, and(c) a haze of its 40 wt % methyl ethyl ketone solution measured according to ASTM D 1003: 15% or less.Type: GrantFiled: November 21, 1996Date of Patent: March 14, 2000Assignee: Shell Oil CompanyInventors: Takao Fukuzawa, Tetsuro Imura, Masayuki Ohta
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Patent number: 6011111Abstract: A thermoplastic composite is prepared by applying a hydroxy-phenoxyether polymer onto the surface of reinforcing fibers or by the in-situ polymerization of mixtures of diepoxides and difunctional species in the presence of reinforcing fibers. The composites can be molded into shaped articles useful for structural materials and parts by conventional thermoforming or other fabrication techniques.Type: GrantFiled: October 18, 1993Date of Patent: January 4, 2000Assignee: The Dow Chemical CompanyInventors: David J. Brennan, Jerry E. White, Daryl R. Calhoun
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Patent number: 5962602Abstract: An epoxy sealer/healer formulation for sealing and strengthening cracked concrete comprising an epoxy resin, an amine and a dialkylene triamine-alkylene oxide adduct, where the formulation provides a modulus and/or compressive strength at least that of uncracked concrete and effective for penetrating a concrete crack at a rate of at least 10 mm/min for a crack 0.5 mm wide when applied by gravity feed. The epoxy sealer/healer preferably has a viscosity of less than 100 centipoise and a tack-free time of less than 12 hours. The epoxy sealer/healer is advantageous in being able to bond to moist concrete surfaces. A method of using the epoxy sealer/healer for sealing and restoring the strength of cracked concrete is also set forth.Type: GrantFiled: February 29, 1996Date of Patent: October 5, 1999Assignee: Sika Corporation USAInventors: Stuart J. Hartman, Michael C. Coddington, David C. Elmendorf, Norman Blank
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Patent number: 5945500Abstract: Methods for preparing low free resorcinol resins are disclosed. These methods generally comprise reacting a resin with an aromatic olefinic compound; suitable resins include one or more resins selected from the group consisting of a dihydric phenol, a polyhydric phenol, a dihydric phenolic novolak resin and a polyhydric phenolic novolak resin; the addition product of at least one of these resins and at least one compound selected from the group consisting of a monooxirane compound and a polyoxirane compound; and a phenol or alkyl or aralkyl substituted mono- or dihydric phenol modified form of these resins. The resins produced by this method are also disclosed, as are rubber compositions utilizing the resin produced by this method.Type: GrantFiled: August 6, 1998Date of Patent: August 31, 1999Assignee: Indspec Chemical Corp.Inventors: Raj B. Durairaj, Alex Peterson, Jr.
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Patent number: 5945504Abstract: An episulfide which has an alicyclic, aromatic or heterocyclic skeleton and has two or more moieties represented by the formula ##STR1## wherein X is S or O, and S is in an amount of 50% or more, on the average, of the total of S and O constituting a three-membered ring. A cured material obtained by polymerizing this episulfide compound is a desirable optical material for various uses, particularly as a lens material for spectacles.Type: GrantFiled: January 13, 1997Date of Patent: August 31, 1999Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Akikazu Amagi, Nobuyuki Uemura, Motoharu Takeuchi, Kenichi Takahashi, Minoru Ohashi, Hiroshi Horikoshi, Masanori Shimuta
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Patent number: 5939508Abstract: A copolymer is formed from reacting, within a melt, a phthalonitrile resin with an epoxy resin having at least three epoxy groups. In an alternative embodiment, a copolymer is formed by reacting a phthalonitrile resin with an epoxy resin, at least one of the epoxy and phthalonitrile resins having a perfluorinated carbon. The copolymers of the present invention have exceptional thermal stability and a low affinity for water.Type: GrantFiled: March 31, 1997Date of Patent: August 17, 1999Assignee: The United States of America as represented by the Secretary of the NavyInventor: Teddy M. Keller
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Patent number: 5936056Abstract: Methods for preparing low free resorcinol resins are disclosed. These methods generally comprise reacting a resin with an aromatic olefinic compound; suitable resins include one or more resins selected from the group consisting of a dihydric phenol, a polyhydric phenol, a dihydric phenolic novolak resin and a polyhydric phenolic novolak resin; the addition product of at least one of these resins and at least one compound selected from the group consisting of a monooxirane compound and a polyoxirane compound; and a phenol or alkyl or aralkyl substituted mono- or dihydric phenol modified form of these resins. The resins produced by this method are also disclosed, as are rubber compositions utilizing the resin produced by this method.Type: GrantFiled: March 7, 1997Date of Patent: August 10, 1999Assignee: Indspec Chemical CorporationInventors: Raj B. Durairaj, Alex Peterson, Jr.
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Patent number: 5900468Abstract: The epoxy resin composition which comprises both components (A) an epoxy compound having at least two epoxy groups in a molecule and (B) a polyphenol compound containing a trisphenol compound represented by general formula (I) described below ##STR1## in which R.sub.1 is a methyl group, n is an integer of 0 to 2, and Ar is a group selected from ##STR2## in which R.sub.2 and R.sub.3 are each individually selected from an alkyl group having a carbon number of 1 to 6, an alkoxy group having a carbon number of 1 to 6, or a halogen atom, and m and p are an integer of 0 to 2.Type: GrantFiled: February 27, 1998Date of Patent: May 4, 1999Assignee: Shell Oil CompanyInventors: Mareki Miura, Yoshinobu Ohnuma
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Patent number: 5847027Abstract: Hardeners for elastic epoxy resin systems, obtained by reaction of(A) reaction products of epoxide compounds (A1) with sterically hindered amines (A3), and/or(B) cyclic carbonates prepared from the compounds (A) and carbon dioxide, and/or(C) cyclic carbonates prepared from reaction products(C1) of epoxide compounds (C11) with polyoxyalkyleneamines (C13) and carbon dioxide, and, if desired(D) additional epoxide compounds or unreacted residues of the initial epoxides for the preparation of (A), (B) and (C), with(E) polyamines having at least two secondary amino groups, and(F) if desired, further reactants, each of the epoxide compounds (A1) and (C11) containing at least two epoxide groups, and it being possible for monoepoxides to be admixed in each case, if desired.Type: GrantFiled: April 1, 1996Date of Patent: December 8, 1998Assignee: Vianova Resins GmbHInventors: Manfred Marten, Claus Godau, Uwe Neumann
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Patent number: 5814373Abstract: Hydroxy-functional polyethers having a "cardo" diphenylene group in their backbones are prepared by contacting at least one dinucleophilic monomer with at least one diglycidyl ether of a cardo bisphenol, such as bis(hydroxyphenyl)fluorene, phenolphthalein, or phenolphthalimidine or a substituted cardo bisphenol, such as a substituted bis(hydroxyphenyl)fluorene, a substituted phenolphthalein or a substituted phenolphthalimidine, under conditions sufficient to cause the nucleophilic moieties of the dinucleophilic monomer to react with epoxy moieties to form a polymer backbone containing pendant hydroxy moieties and ether, imino, amino, sulfonamido or ester linkages. These polyethers possess a combination of high barrier to oxygen transmission (i.e., oxygen transmission rate less than 10.0 cm.sup.3 -mil/100 in.sup.2 -atm-day to oxygen) and high heat resistance (i.e., Tg above 120.degree. C.).Type: GrantFiled: October 1, 1993Date of Patent: September 29, 1998Assignee: Dow Chemical CompanyInventors: Jerry E. White, H. Craig Silvis, Stephen E. Bales, Michael N. Mang, Muthiah N. Inbasekaran
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Patent number: 5776374Abstract: The present invention relates to crosslinkable thermoplastic compositions comprising a plurality of crosslinkable moieties, capable of undergoing addition polymerization, incorporated by functionalization of the precursor poly(hydroxy ethers). The poly(hydroxy ethers) comprise recurring moieties derived from aromatic dihydroxy compounds. The crosslinkable polymeric compositions are crosslinked to obtain crosslinked thermoset polymeric compositions of the invention. The polymeric compositions of the inventions can be suitably used either as an active guiding layer, and/or as a NLO active upper and lower cladding layers in an electro-optic device. The polymeric compositions can also be used as non-NLO polymers for the upper and lower cladding layers, prior to orientation by the application of an electric field.Type: GrantFiled: November 7, 1995Date of Patent: July 7, 1998Assignee: The Dow Chemical CompanyInventors: Mark D. Newsham, Michael N. Mang, Robert J. Gulotty, Jr., Dennis W. Smith, Jr.
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Patent number: 5736620Abstract: Epoxy resins containing rodlike mesogenic moieties are prepared from phenolic hydroxyl containing compounds which contain such moieties.Type: GrantFiled: May 25, 1995Date of Patent: April 7, 1998Assignee: The Dow Chemical CompanyInventors: Jimmy D. Earls, Robert E. Hefner, Jr., Paul M. Puckett
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Patent number: 5644003Abstract: An epoxy resin composition which comprises: (a) an epoxy resin having at least two epoxy groups in the molecule, (b) an epoxy resin curing agent, (c) a cure accelerator, (d) an aromatic polyamide pulp and (e) an inorganic filler as the essential components, the aromatic polyamide pulp (d) being contained in an amount of 0.5 to 10% by weight based on the total weight of the component (a), the component (b) and the component (d), and the inorganic filler (e) being contained in an amount of 75 to 94% by weight based on the total weight of the component (a), the component (b), the component (c) and the component (e), and a semiconductor device sealed with the above epoxy resin composition. The cured product of the epoxy resin composition is good in balance of hot impact strength and hot flexural strength and hence, the semiconductor device sealed with the epoxy resin composition is excellent in soldering resistance.Type: GrantFiled: July 18, 1995Date of Patent: July 1, 1997Assignee: Sumitomo Chemical Company, Ltd.Inventors: Noriyuki Arai, Yutaka Shiomi, Hiroshi Nakamura, Noriaki Saito
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Patent number: 5641852Abstract: Disclosed is a thermosetting resin composition comprising cyanate resin, a compound containing at least one or more than one of a phenolic hydroxyl radical and an epoxy resin, wherein said resin has excellent adhesive and heat resistant properties while at the same time possessing a low hardening contraction rate and contributing to higher dimensional stability, and method of making the same.Type: GrantFiled: January 11, 1996Date of Patent: June 24, 1997Assignee: Kanegafuchi Kagaku Kogyo Kabushiki KaishaInventors: Hiroyuki Tsuji, Shoji Hara, Hirosaku Nagano
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Patent number: 5606006Abstract: Cure of a novel trisepoxy resin-based composition provides a thermoset having high Tg, low dielectric constant, low water absorption and good flexural strength.Type: GrantFiled: April 8, 1996Date of Patent: February 25, 1997Assignee: Shell Oil CompanyInventor: Pen-Chung Wang