Material Contains A Group Ia Metal Atom (li, Na, K, Rb, Cs, Fr) Patents (Class 528/95)
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Patent number: 11518843Abstract: Polymer composite materials and methods of preparation are discussed. The composite material may comprise a polyurethane foam and a plurality of inorganic particles dispersed in the polyurethane foam. The composite material may have moisture movement properties, such that (a) a sample of the composite material having a length of 48 inches has a moisture movement of less than 0.15% along the length, and/or (b) a sample having a length of 6 inches has a moisture movement of less than 0.8% along the length, when submerged in 45° C. distilled water for 14 days.Type: GrantFiled: February 26, 2019Date of Patent: December 6, 2022Assignee: Westlake Royal Building Products Inc.Inventors: Edward F. Cassidy, Russell L. Hill, Robert F. Rathbone, Xi Zhang, Ying Zhang, Qi Chen, Amitabha Kumar
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Patent number: 9181464Abstract: Provided are an adhesive resin composition that is halogen-free, has good adhesiveness, solder heat resistance, and flame retardancy, and has good flow characteristics, and a laminate and a flexible printed wiring board using the same. The adhesive resin composition contains a phosphorus-containing epoxy resin and/or a phosphorus-containing phenoxy resin, a phosphorus-containing polyester resin having a weight-average molecular weight of more than 20,000 and 150,000 or less, another thermoplastic resin, and a curing agent. The adhesive resin composition preferably further contains a benzoxazine compound. Preferably, substantially no inorganic filler is mixed in the adhesive resin composition.Type: GrantFiled: January 18, 2010Date of Patent: November 10, 2015Assignees: SUMITOMO ELECTRIC INDUSTRIES, LTD., SUMITOMO ELECTRIC PRINTED CIRCUITS, INC.Inventors: Shingo Kaimori, Jun Sugawara, Akira Mizoguchi, Syougo Asai, Takuma Yoshisaka, Naota Uenishi
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Publication number: 20150018456Abstract: Disclosed herein are polyglycidyl ethers of the formula: where R, m, Q, p and Z are as defined here. Also disclosed are methods of forming said polyglycidyl ethers and methods of using said polyglycidyl ethers to make epoxy resin oligomers and polymers, including powder coatings.Type: ApplicationFiled: February 22, 2013Publication date: January 15, 2015Inventors: Robert E. Hefner, JR., Erich J. Molitor
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Patent number: 8809470Abstract: A polymerizable epoxy compound composition containing an anionic polymerization initiator which can be easily produced, can attain a high polymerization rate and a high degree of polymerization, and can realize an epoxy polymer having properties unobtainable so far, an improvement in cured polymer properties, etc.; and a method of polymerizing an epoxy compound. The composition is an anionically polymerizable composition comprising a monofunctional epoxy compound or a di- or more functional epoxy resin and a polymerization initiator, the polymerization initiator comprising the potassium or sodium salt of a monocarboxylic acid monomer. The method, which is for producing a polymer of epoxy compounds, comprises polymerizing a monofunctional epoxy compound or a di- or more functional epoxy resin by anionic polymerization with the aid of the potassium or sodium salt of a monocarboxylic acid monomer.Type: GrantFiled: August 24, 2005Date of Patent: August 19, 2014Assignee: Nagase Chemtex CorporationInventor: Hirofumi Nishida
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Publication number: 20130079489Abstract: A process comprising: a) contacting a polyhydric phenol and an epihalohydrin in the presence of a catalyst under reaction conditions to form an organic feed comprising a bishalohydrin ether and a solvent; b) contacting the organic feed and an aqueous feed comprising an inorganic hydroxide in a reciprocating-plate column reactor under reaction conditions to form a dispersed aqueous phase and an organic product; and c) collecting the organic product comprising an epoxy resin, is disclosed.Type: ApplicationFiled: August 31, 2012Publication date: March 28, 2013Applicant: Dow Global Technologies LLCInventors: Thomas C. Young, William G. Worley, Robert M. Drake
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Publication number: 20120141793Abstract: A method of making an epoxy resin by condensing a polyphenol and a compound selected from epichlorohydrin, 1,3-dichloro-2-propanol, and homologs thereof in water that is free of added organic solvent at an elevated temperature and in the presence of a catalyst. The method comprises carrying out the condensation in the presence of a dispersion promoting agent whose solubility in water decreases with increasing temperature.Type: ApplicationFiled: August 24, 2009Publication date: June 7, 2012Inventors: Leming Gu, Philip J. Carlberg, David L. Burow
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Publication number: 20120101246Abstract: An epoxy resin represented by general formula (I) satisfying numerical formula (1) with hydrolytic halogen of 0.05 wt. % or less, said epoxy resin produced as follows: after dissolving 0.8 to 1.3 mole of epihalohydrin to 1 mole of divalent phenol in a solvent, a pre-reaction is performed over 30 to 70 minutes by adding dropwise 0.25-0.35 mole of 30˜50% aqueous solution of alkali metal hydroxide over 30 to 70 minutes thereto, and thereafter, 0.65-0.75 mole of the remaining 30˜50% aqueous solution of alkali metal hydroxide is added dropwise over about 1 hour to complete the reaction over 1 to 3 hours. 0.5?X/Y?1.Type: ApplicationFiled: October 24, 2011Publication date: April 26, 2012Applicant: KUKDO CHEMICAL CO., LTD. (KOREAN CORPORATION)Inventors: Masayoshi HANAFUSA, Shuya SHINOHARA, Chongsoo PARK, Kyungho Park, Deuk-sung BAE, Seok LEE
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Patent number: 7960483Abstract: An adamantane derivative of formula (I), a compound of formula (VII) or (VIII), compositions containing them, and optical electronic members using the resin compositions. In the formulas, W represents, for example, a hydrogen atom, X is bonded to a bridge-head adamantane carbon and represents, for example, a group of represented by the general formula (II), Y represents a group of formula (V) or (VI), R1 represents a methyl group or an ethyl group, R2 represents a C1 to C10 hydrocarbon group which may contain O or S, m is an integer of 2 to 4, k is an integer of 0 to (16?m) and p and q are each an integer of 1 to 5.Type: GrantFiled: February 1, 2007Date of Patent: June 14, 2011Assignee: Idemitsu Kosan Co., Ltd.Inventors: Hajime Ito, Yasunari Okada, Hideki Yamane, Nobuaki Matsumoto
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Publication number: 20090036631Abstract: Disclosed is a polymer which is useful for the preparation of an epoxy resin composition or a cured product thereof in film or sheet exhibiting high heat resistance, high thermal conductivity, low thermal expansion, high gas barrier property, and high toughness. The polymer is a thermoplastic aromatic ether polymer comprising a unit represented by the following general formula (1) at a ratio of 10 to 100 mol % and having a weight average molecular weight of 3,000 or more; in formula (1), X is an oxygen atom or a sulfur atom, R1 and R2 each is a hydrogen atom, an alkyl group of 1 to 8 carbon atoms, an aryl group, an alkoxy group, an aralkyl group, or a halogen atom, and n is a number of 1 to 3.Type: ApplicationFiled: January 10, 2007Publication date: February 5, 2009Applicant: NIPPON STEEL CHEMICAL CO., LTD.Inventors: Masashi Kaji, Koichiro Ogami
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Patent number: 7067233Abstract: A compound including an epoxy group that has a heat curing property and a chalcone group that has a radiation curing property is represented by the following formula: wherein n is an integer from 1 to 10,000, and each of R1, R2, R3, R4, R5, R6, R7 and R8 is selected from a group consisting of a hydrogen atom, alkyl group, alkoxy group, halogen atom and nitro group. The compound has a high curing efficiency. A photoresist composition including the compound above substantially prevents the formation of remnant in a photoresist pattern used in the manufacturing of a color filter. In addition, the color filter pattern that is formed using the photoresist composition has high color reproductivity and brightness.Type: GrantFiled: March 24, 2004Date of Patent: June 27, 2006Assignee: Samsung Electronics Co., Ltd.Inventors: Yoon-Ho Kang, Dong-Ho Bae, Jang-Sub Kim
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Patent number: 6887919Abstract: A pressure sensitive adhesive composed of a mixture comprising a) a styrene block copolymer having a star-shaped structure and a molecular weight Mw of more than 300,000 g/mol, or having elastomer blocks which contain more than 30% by weight of 1,2-linked diene in their block structure, or both, and which is crosslinkable by exposure to UV-light or electron beams, and b) one or more block copolymers composed of vinylaromatic blocks and elastomer blocks, the block polyvinylaromatic content being greater than 20%, and c) one or more tackifier resins.Type: GrantFiled: February 3, 2003Date of Patent: May 3, 2005Assignee: tesa AGInventors: Thorsten Krawinkel, Bernd Lühmann, Renke Bargmann
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Patent number: 6838529Abstract: A polyester composition prepared by melting and blending a polyester with a glycidyl ester compound, a glycidyl ether compound and a catalyst has good hydrolysis resistance and, when melted, gives little gas generation and undergoes little viscosity change. It is most favorable for parts of automobile, electric and electronic appliances such as connectors.Type: GrantFiled: November 20, 2001Date of Patent: January 4, 2005Assignee: Toray Industries, Inc.Inventors: Sadanori Kumazawa, Hiroyuki Ohme, Kenichi Utazaki, Jiro Kumaki
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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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Patent number: 6773754Abstract: Aqueous solutions of inorganic nitrate salts are used to accelerate the gelling of epoxy gelcoat resins without adversely affecting the glass transition temperature of the finally cured gelcoat. The aqueous accelerants may be used to accelerate gelling of gelcoats that are formed during initial fabrication of composite parts. The aqueous acclerants are also useful for shortening the gel time of gelcoats that are intended for use in repairing damaged structures.Type: GrantFiled: December 10, 2002Date of Patent: August 10, 2004Assignee: Hexcel Composites, Ltd.Inventor: Mark Whiter
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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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Publication number: 20030120022Abstract: This invention relates to a process for the preparation of highly-branched polyols by polymerisation of glycidol in the presence of a hydrogen-active starter compound with basic catalysis, wherein glycidol is added in dilute solution and the solvent used for the dilution is continuously distilled off. The polyols thus prepared are colourless, contain as the core unit solely the starter compound used and have polydispersities of less than 1.7.Type: ApplicationFiled: January 2, 2003Publication date: June 26, 2003Inventors: Alexander Sunder, Rolf Mulhaupt
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Publication number: 20020022709Abstract: The present invention provides a process for eliminating contaminants from epihalohydrin-derived epoxy resins. Another embodiment of the present invention is an epoxy product formed using said process. Yet another embodiment of the present invention is an epoxy derived in part from epihalohydrin wherein said epoxy is has a hydrolyzable halogen content of less than 10 ppm and an epoxide equivalent weight within 2 percent of the theoretical epoxide equivalent weight.Type: ApplicationFiled: October 9, 2001Publication date: February 21, 2002Applicant: 3M Innovative Properties CompanyInventor: Roger A. Mader
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Patent number: 6235870Abstract: Process for the preparation of compounds of the formula wherein Hal represents chlorine, bromine or iodine and preferably chlorine, wherein Ra represents hydrogen or a residue comprising one or more additional groups of the formula, from compounds wherein R2 represents hydrogen or a residue comprising one or more additional groups of the formula by reaction with gaseous hydrogen halide in the presence of a catalytic amount of an organic acid; process for the preparation of epoxy compounds starting from the reaction to produce a compound of formula (III) which is converted to a compound of formula (A) that is dehydrohalogenated to form the epoxy rings of a diepoxy compound.Type: GrantFiled: September 29, 1999Date of Patent: May 22, 2001Assignee: Shell Oil CompanyInventors: Jozef Jacobus Titus Smits, Judith Johanna Berendina Walhof
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Patent number: 6107419Abstract: Present invention relates to a process for preparing a high molecular weight epoxy resin which has a weight average molecular weight value more than 40,000 and an epoxy equivalent weight less than 10,000 g/eq. This high molecular weight epoxy is prepared by a reaction of a divalent epoxy resin with a bisphenol compound in the presence of a catalyst and a solvent characterized in utilizing 1.10 to 1.03/1 of molar ratio of epoxy group/phenolic hydroxyl group.Type: GrantFiled: December 10, 1997Date of Patent: August 22, 2000Assignee: Shell Oil CompanyInventors: Yoshikazu Kobayashi, Takaya Shinmura, Yojiro Yamamoto
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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: 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: 6001873Abstract: This invention relates to a process for preparing a high purity epoxy resin comprising reacting an aromatic compound containing hyroxyl or amino group with an excess amount of an epihalohydrin in the presence of hydroxides of alkali metal or alkali earth metal in one or more low-boiling aprotic cosolvents under normal or reduced pressure with dewatering to obtain a high purity epoxy resin with low level of hydrolyzable halides.Type: GrantFiled: May 30, 1997Date of Patent: December 14, 1999Assignee: Chang Chun Plastics Co., Ltd.Inventors: Kuen Yuan Hwang, Hong-Hsing Chen, An Bang Duh, Chie-Yih Ju
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Patent number: 6001954Abstract: Process for the preparation of compounds of the formula ##STR1## wherein Hal represents chlorine, bromine or iodine and preferably chlorine, wherein R.sub.a represents hydrogen or a residue comprising one or more additional groups of the formula, ##STR2## from compounds ##STR3## wherein R.sub.2 represents hydrogen or a residue comprising one or more additional groups of the formula ##STR4## by reaction with gaseous hydrogen halide in the presence of a catalytic amount of an organic acid. Epoxy resins are prepared via the reaction of a compound of formula (A) in the presence of a basic compound.Type: GrantFiled: February 6, 1998Date of Patent: December 14, 1999Assignee: Shell Oil CompanyInventors: Jozef Jacobus Titus Smits, Judith Johanna Berendina Walhof
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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: 5969036Abstract: In accordance with the present invention, there are provided novel compositions for attaching semiconductor devices to substrates. Invention compositions comprise liquid monomer vehicle comprising hydrophobic cyanate ester monomer(s) and epoxy monomer(s), electrically and/or thermally conductive filler, a metal catalyst, and an imidazole, preferably in the substantial absence of non-reactive diluents.Type: GrantFiled: June 20, 1997Date of Patent: October 19, 1999Assignee: The Dexter CorporationInventor: Stephen M. Dershem
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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: 5912317Abstract: An improved oxazolidine-based hardener to be used with a resorcinol resin or a tannin resin as the adhesive for the bonding of wood articles. Preferably, an oxazolidine is combined with particulate silica, and the resin is combined with a base such as NaOH. The adhesive based on the improved hardener can be used to glue wood particles to pass wet strength requirements after the glue is cured at room temperature for under 24 hours. The improved hardener composition is storage stable; it can be prepared anytime before its use and, thus, eliminate the need to prepare a hardener immediately prior to the glue use. Since it is formaldehyde-free; it eliminates the safety issues associated with handling formaldehyde or paraformaldehyde. Also, the hardener provides flexible gel time or working time. Since the resins can be cured at room temperature, heating in an oven is not needed but could be used to reduce curing time. If radio frequencies are used to cure the resins, the exposure time can be reduced.Type: GrantFiled: August 15, 1997Date of Patent: June 15, 1999Assignee: ANGUS Chemical CompanyInventor: Gaoming Wu
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Patent number: 5558939Abstract: A method for producing an epoxy polyetherpolyol having 15 to 75 wt % epoxy comprising heating a polyol and catalyst to initiate condensation, removing water, introducing sufficient epoxy into the reaction mixture to give 15 to 75 wt % epoxy in the product. Generally, between 0.5 and 1.19 moles of water per mole of polyol are removed. In one embodiment at least 95 wt % of all of the polyol is introduced initially into the reaction zone. In another embodiment the condensation is terminated prior to 93 percent completion. Also provided are novel compositions suitable for drilling fluids, adhesives and coatings.Type: GrantFiled: July 28, 1995Date of Patent: September 24, 1996Assignee: Shell Oil CompanyInventors: George C. Blytas, Arthur H. Hale
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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
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Patent number: 5278260Abstract: A process for the preparation of epoxy resins having a specific reproducible content of .alpha.-glycol groups, which process comprises adding at least 0.0085 mol of glycidol or glycidol precursor compound per hydroxy-equivalent of a phenolic compound A which contains 2, 3 or 4 phenolic hydroxyl groups during the reaction of said phenolic compound A with an epihalohydrin which is unsubstituted or substituted in 2- or 3-position by C.sub.1 -C.sub.4 alkyl. The products may be used for surface protection.Type: GrantFiled: October 13, 1992Date of Patent: January 11, 1994Assignee: Ciba-Geigy CorporationInventors: Werner Schaffner, Dimiter Hadjistamov
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Patent number: 5212261Abstract: Latent, heat-curable epoxy resin compositions containing metal carboxylate curing systems provide exceptional latency, particularly at elevated temperature, as well as facile curing, high T.sub.g and adhesive strength, and other attractive properties. The metal carboxylates comprise alkali metals and alkaline earth metals, aromatic and aliphatic metal carboxylates. The preferred curing systems comprise synergistic combinations of the metal carboxylates with cure modifiers.Type: GrantFiled: December 17, 1990Date of Patent: May 18, 1993Assignee: Henkel Research CorporationInventor: Thomas J. Stierman
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Patent number: 5098964Abstract: A process is disclosed for preparing a low-chlorine tetrafunctional epoxy resin which employs crystallization of the epoxy resin from solution in a finishing step of the preparation process. The process involves (a) contacting, in a basic reaction medium, epichlorohydrin and a tetraphenol of ethane to produce a reaction product mixture containing a polyglycidyl ether of the tetraphenol of ethane; (b) dissolving the polyglycidyl ether in an organic solvent and, optionally, contacting the polyglycidyl ether with a dehydrochlorination agent; and (c) reducing the temperature of the organic solvent so as to effect crystallization of a low-chlorine fraction of the polyglycidyl ether.Type: GrantFiled: January 31, 1991Date of Patent: March 24, 1992Assignee: Shell Oil CompanyInventors: Ronald S. Bauer, Kailash C. B. Dangayach
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Patent number: 5098965Abstract: A process is disclosed for preparing a low-chlorine epoxy resin which employs crystallization of the epoxy from solution in a finishing step of the preparation process. The process involves (a) contacting, in a basic reaction medium, epichlorohydrin and a biphenol to produce a reaction product mixture containing a diglycidyl ether of the biphenol; (b) dissolving the diglycidyl ether in an organic solvent and, optionally, contacting the diglycidyl ether with a dehydrochlorination agent; and (c) reducing the temperature of the organic solvent so as to effect crystallization of a low-chlorine fraction of the diglycidyl ether.Type: GrantFiled: January 31, 1991Date of Patent: March 24, 1992Assignee: Shell Oil CompanyInventors: Ronald S. Bauer, Kailash C. B. Dangayach
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Patent number: 5075386Abstract: A cross-linkable hot-melt adhesive is prepared by mixing an acid graft modified propylene/olefin copolymer with an epoxy cross-linking agent and a tertiary amine catalyst. The adhesive is cross-linked at an elevated temperature such as when melt mixing the components.Type: GrantFiled: April 12, 1990Date of Patent: December 24, 1991Assignee: Eastman Kodak CompanyInventor: Jeffrey J. Vanderbilt
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Patent number: 5028686Abstract: Epoxy resins which are relatively low in total bound halide are prepared by concurrently and continuously adding a mixture of (1) a mixture of an epihalohydrin, a compound containing an average of more than one group reactive with a vicinal epoxide group and a solvent and (2) an aqueous or organic solution of an alkali or alkaline earth metal hydroxide; to (3) a mixture of epihalohydrin and a solvent.Type: GrantFiled: September 18, 1990Date of Patent: July 2, 1991Assignee: The Dow Chemical CompanyInventors: Zeng-Kun Liao, Chun S. Wang
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Patent number: 4877857Abstract: The construction costs of a process for preparing epoxy compounds from aromatic compounds containing an active hydrogen atom reactive with an epihalohydrin by reacting such compounds with an epihalohydrin in the presence of an alkali metal hydroxide while controlling the water content in the reaction mixture and subsequently removing the alkali metal halide salt from the reaction mixture is made less costly by employing a water extraction means to remove the alkali metal halide salts from the reaction product mixture containing the epoxy product.Type: GrantFiled: January 11, 1989Date of Patent: October 31, 1989Assignee: The Dow Chemical CompanyInventors: Robert P. Shirtum, Elaine B. Darby
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Patent number: 4831101Abstract: A process for the preparation of at least one member of the group consisting of monoglycidyl and polyglycidyl compounds comprising reacting a member of the group consisting of mono- and polyvalent phenols, aromatic amines and aromatic carboxylic acids with an epihalohydrin substantially free of halogenated hydrocarbons.Type: GrantFiled: September 24, 1987Date of Patent: May 16, 1989Assignee: Rutgerswerke AGInventors: Karl Jellinek, Bert Meier, Rolf Herzog, Gunter Reinsch
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Patent number: 4795791Abstract: Epoxy resins of increased functionality are prepared by branching the epoxy resin in the presence of a lithium or cesium compound as a branching catalyst until the desired functionality is obtained and thereafter terminating the branching reaction. Since the lithium and cesium compounds are not deactivated by the aliphatic chloride typically found in an epoxy resin, the branching reaction can effectively be conducted even at low concentrations of the lithium or cesium compound. Termination of the branching reaction is conducted by cooling the branching reaction mixture or by the addition of a deactivating agent which stops or effectively reduces the rate of the branching reaction. Due to the low conecntration at which the branching catlayst can be employed, the resulting branched epoxy resins can be prepared without visible turbidity.Type: GrantFiled: November 27, 1987Date of Patent: January 3, 1989Assignee: The Dow Chemical CompanyInventors: Raymond A. Koenig, Gunter H. Haertel
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Patent number: 4778863Abstract: Glycidyl derivatives of compounds containing --OH, --NH.sub.2 and/or --COOH groups are prepared by reacting in the presence of a mixture of solvents, at least one of which is a polar aprotic solvent, an excess of an epihalohydrin with a compound containing --OH, --NH.sub.2 and/or --COOH groups while continuously or incrementally adding an alkali metal hydroxide to the mixture and removing water from the reaction by codistillation with epihalohydrin and the solvents.Type: GrantFiled: August 13, 1987Date of Patent: October 18, 1988Assignee: The Dow Chemical CompanyInventors: Chun S. Wang, Zeng-kun Liao
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Patent number: 4769437Abstract: Phenolic resins are produced by reacting a substituted alcohol or epoxy compound with a phenol compound in the presence of an alkali salt-forming compound. The phenolic resin may be utilized as molding material, as a coating agent and as an adhesive.Type: GrantFiled: September 18, 1987Date of Patent: September 6, 1988Inventor: David H. Blount
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Patent number: 4756787Abstract: A co-curable composition, having utility as a first part of a two-part cationically curable composition and containing a latent curing component which is reactive with a latent curing component in a second part of the two-part composition to form curingly effective cations for the two-part composition, such co-curable composition comprising: (i) a cationically polymerizable material, and (ii) a dioxane-complexed metal salt of a non-nucleophilic anion. Also disclosed is a two-part composition curable by contact of respective parts with one another, comprising first and second parts of the aforementioned types. A preferred class of cation species comprises carbenium ions derived from reaction of an organic halide compound, as the first component, with a metal salt of a non-nucleophilic anion such as SbCl.sub.6.sup.-, SbCl.sub.3.sup.-, SbF.sub.6.sup.-, AsF.sub.6.sup.-, SnCl.sub.5.sup.-, PF.sub.6.sup.-, BF.sub.4.sup.-, CF.sub.3 SO.sub.3.sup.-, and ClO.sub.4.sup.-, as the second component.Type: GrantFiled: November 6, 1987Date of Patent: July 12, 1988Assignee: Loctite CorporationInventors: Kieran F. Drain, David J. Dunn
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Patent number: 4751280Abstract: Epoxy resins are prepared by (a) adding an alkali metal hydroxide solution to a mixture containing an excess of an epihalohydrin, a phenolic hydroxyl-containing or an aromatic amine-containing compound and an organic solvent which codistills with water and the epihalohydrin, (b) conducting the reaction under reduced pressure while continuously removing water by codistillation, (c) separating the water from the distillate and returning the epihalohydrin and organic solvent to the reaction mixture, (d) drying the reaction mixture, (e) removing insoluble materials by suitable mechanical separation means, (f) washing the resin/epihalohydrin/organic solvent mixture with water so as to substantially remove water soluble materials, (g) drying the epihalohydrin/resin mixture, and (h) recovering the resultant epoxy resin from the resin/epihalohydrin/organic solvent mixture by any suitable means. This process produces an epoxy resin which is low in hydrolyzable halide and total halide.Type: GrantFiled: August 19, 1987Date of Patent: June 14, 1988Assignee: The Dow Chemical CompanyInventors: Ha Q. Pham, Benny B. Gammill
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Patent number: 4746725Abstract: Resinous compositions are prepared by the reaction of a composition comprising cyclic polycarbonate oligomers with at least one polyepoxide compound, in the presence of a polycarbonate formation catalyst. The cyclic polycarbonate oligomer composition is preferably a mixture of oligomers of varying degrees of polymerization, and the polyepoxy compound is preferably triglycidyl isocyanurate or a bis-epoxy-terminated bisphenol A-epichlorohydrin concentrate. There may also be present a polycarbonate crosslinking agent. The product of the reaction is a crosslinked polycarbonate network. The method is particularly useful in reactive processing operations such as reaction injection molding.Type: GrantFiled: February 25, 1987Date of Patent: May 24, 1988Assignee: General Electric CompanyInventors: Thomas L. Evans, Niles R. Rosenquist, Edgar E. Bostick
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Patent number: 4722983Abstract: A process for the preparation of glycidyl compounds by reacting a compound containing at least one phenolic group with at least the equivalent amount, based on the phenolic group, of a halohydrin in a substantially anhydrous, aprotonic solvent in the presence of a solid, substantially anhydrous catalyst, is described, which process comprises carrying out the reaction at a temperature in the range from 40.degree. to 80.degree. C. in the presence of an alkali metal carbonate, an aprotonic dipolar solvent with a static relative dielectric constant of more than 25 (at 25.degree. C.) and a permanent electric dipole moment of more than 2.5 D being used, an additional feature of said solvent being that the transition energy of the solvatochromic absorption band of the dissolved N-(3,5-diphenyl-4-hydroxyphenyl)-2,4,6-triphenylpyridinium perchlorate is in the range from 168 to 197.4 kJ/mole (at 25.degree. C.), or which process comprises carrying out the reaction at a temperature in the range from 60.degree. to 80.Type: GrantFiled: December 8, 1986Date of Patent: February 2, 1988Assignee: Ciba-Geigy CorporationInventors: Charles E. Monnier, Friedrich Stockinger
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Patent number: 4722990Abstract: Epoxy resins of increased functionality are prepared by branching the epoxy resin in the presence of a lithium or cesium compound as a branching catalyst until the desired functionality is obtained and thereafter terminating the branching reaction. Since the lithium and cesium compounds are not deactivated by the aliphatic chloride typically found in an epoxy resin, the branching reaction can effectively be conducted even at low concentrations of the lithium or cesium compound. Termination of the branching reaction is conducted by cooling the branching reaction mixture or by the addition of a deactivating agent which stops or effectively reduces the rate of the branching reaction. Due to the low concentration at which the branching catalyst can be employed, the resulting branched epoxy resins can be prepared without visible turbidity.Type: GrantFiled: August 15, 1985Date of Patent: February 2, 1988Assignee: The Dow Chemical CompanyInventors: Raymond A. Koenig, Guenter H. Haertel
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Patent number: 4711911Abstract: Phenolic resins are produced by reacting a substituted alcohol or epoxy compound with a phenol compound in the presence of an alkali salt-forming compound. The phenolic resin may be utilized as molding material, as a coating agent and as an adhesive.Type: GrantFiled: December 22, 1986Date of Patent: December 8, 1987Inventor: David H. Blount
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Patent number: 4684701Abstract: Advanced epoxy resins having a low total aliphatic halide content are prepared by reacting an epoxy resin having an average of more than one 1,2-epoxide group per molecule with a material having an average of more than one phenolic hydroxyl group per molecule in the presence of a solvent having at least one aliphatic hydroxide group per molecule and a catalytic quantity of an alkali metal hydroxide. These low aliphatic halide-containing advanced epoxy resins are useful in formulations for preparing laminates, moldings, pottings and coatings for the electronics industry.Type: GrantFiled: September 24, 1986Date of Patent: August 4, 1987Assignee: The Dow Chemical CompanyInventors: Chun S. Wang, Robert L. Bowden, Wuu N. Chen
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Patent number: 4661562Abstract: A process for the rapid formation of thermoset polymers by polymerizing a mixture of a polyepoxide with a polycarboxylic acid containing an alkali or alkaline earth metal cationic complex catalyst is disclosed.Type: GrantFiled: November 4, 1985Date of Patent: April 28, 1987Assignee: Ashland Oil, Inc.Inventor: Anil B. Goel
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Patent number: 4624975Abstract: The hydrolyzable halide content of glycidyl ethers prepared by dehydrohalogenating a halohydrin ether intermediate product in the presence of an organic solvent, washing the resultant product with water and distilling the solvent from the organic phase from the water wash step is stabilized when the distillation step is conducted in the presence of a sulfonic acid, sulfonic acid ester, organic sulfate or any combination thereof such as p-toluene sulfonate.Type: GrantFiled: September 20, 1985Date of Patent: November 25, 1986Assignee: The Dow Chemical CompanyInventor: Ha Q. Pham
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Patent number: 4558116Abstract: Epoxy resins low in aliphatic halogen are prepared by reacting a polyhydric phenol with an excess of an epihalohydrin in the presence of a secondary alcohol and an aqueous solution of an alkali metal hydroxide until from 45 to <70 percent of the phenolic hydroxyl groups have reacted; removing unreacted polyhydric phenol therefrom until less than 4% total phenolic hydroxyl remains in the reaction product; dehydrohalogenating the resultant intermediate product and recovering the epoxy resin therefrom.Type: GrantFiled: March 4, 1985Date of Patent: December 10, 1985Assignee: The Dow Chemical CompanyInventors: Walter L. Wernli, Robert P. Shirtum