Material Contains A Group Ia Metal Atom (li, Na, K, Rb, Cs, Fr) Patents (Class 528/95)
  • Patent number: 11518843
    Abstract: 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: Grant
    Filed: February 26, 2019
    Date of Patent: December 6, 2022
    Assignee: Westlake Royal Building Products Inc.
    Inventors: Edward F. Cassidy, Russell L. Hill, Robert F. Rathbone, Xi Zhang, Ying Zhang, Qi Chen, Amitabha Kumar
  • Patent number: 9181464
    Abstract: 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: Grant
    Filed: January 18, 2010
    Date of Patent: November 10, 2015
    Assignees: SUMITOMO ELECTRIC INDUSTRIES, LTD., SUMITOMO ELECTRIC PRINTED CIRCUITS, INC.
    Inventors: Shingo Kaimori, Jun Sugawara, Akira Mizoguchi, Syougo Asai, Takuma Yoshisaka, Naota Uenishi
  • Publication number: 20150018456
    Abstract: 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: Application
    Filed: February 22, 2013
    Publication date: January 15, 2015
    Inventors: Robert E. Hefner, JR., Erich J. Molitor
  • Patent number: 8809470
    Abstract: 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: Grant
    Filed: August 24, 2005
    Date of Patent: August 19, 2014
    Assignee: Nagase Chemtex Corporation
    Inventor: Hirofumi Nishida
  • Publication number: 20130079489
    Abstract: 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: Application
    Filed: August 31, 2012
    Publication date: March 28, 2013
    Applicant: Dow Global Technologies LLC
    Inventors: Thomas C. Young, William G. Worley, Robert M. Drake
  • Publication number: 20120141793
    Abstract: 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: Application
    Filed: August 24, 2009
    Publication date: June 7, 2012
    Inventors: Leming Gu, Philip J. Carlberg, David L. Burow
  • Publication number: 20120101246
    Abstract: 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: Application
    Filed: October 24, 2011
    Publication date: April 26, 2012
    Applicant: KUKDO CHEMICAL CO., LTD. (KOREAN CORPORATION)
    Inventors: Masayoshi HANAFUSA, Shuya SHINOHARA, Chongsoo PARK, Kyungho Park, Deuk-sung BAE, Seok LEE
  • Patent number: 7960483
    Abstract: 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: Grant
    Filed: February 1, 2007
    Date of Patent: June 14, 2011
    Assignee: Idemitsu Kosan Co., Ltd.
    Inventors: Hajime Ito, Yasunari Okada, Hideki Yamane, Nobuaki Matsumoto
  • Publication number: 20090036631
    Abstract: 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: Application
    Filed: January 10, 2007
    Publication date: February 5, 2009
    Applicant: NIPPON STEEL CHEMICAL CO., LTD.
    Inventors: Masashi Kaji, Koichiro Ogami
  • Patent number: 7067233
    Abstract: 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: Grant
    Filed: March 24, 2004
    Date of Patent: June 27, 2006
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Yoon-Ho Kang, Dong-Ho Bae, Jang-Sub Kim
  • Patent number: 6887919
    Abstract: 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: Grant
    Filed: February 3, 2003
    Date of Patent: May 3, 2005
    Assignee: tesa AG
    Inventors: Thorsten Krawinkel, Bernd Lühmann, Renke Bargmann
  • Patent number: 6838529
    Abstract: 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: Grant
    Filed: November 20, 2001
    Date of Patent: January 4, 2005
    Assignee: Toray Industries, Inc.
    Inventors: Sadanori Kumazawa, Hiroyuki Ohme, Kenichi Utazaki, Jiro Kumaki
  • Patent number: 6794478
    Abstract: 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: Grant
    Filed: September 24, 2002
    Date of Patent: September 21, 2004
    Assignee: Dainippon Ink and Chemicals, Inc.
    Inventors: Ichiro Ogura, Kazuo Arita
  • Patent number: 6773754
    Abstract: 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: Grant
    Filed: December 10, 2002
    Date of Patent: August 10, 2004
    Assignee: Hexcel Composites, Ltd.
    Inventor: Mark Whiter
  • Patent number: 6599960
    Abstract: 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: Grant
    Filed: July 13, 2000
    Date of Patent: July 29, 2003
    Assignee: Espe Dental AG
    Inventors: Gunther Eckhardt, Gunther Lechner, Erich Wanek, Ursula Somnitz
  • Publication number: 20030120022
    Abstract: 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: Application
    Filed: January 2, 2003
    Publication date: June 26, 2003
    Inventors: Alexander Sunder, Rolf Mulhaupt
  • Publication number: 20020022709
    Abstract: 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: Application
    Filed: October 9, 2001
    Publication date: February 21, 2002
    Applicant: 3M Innovative Properties Company
    Inventor: Roger A. Mader
  • Patent number: 6235870
    Abstract: 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: Grant
    Filed: September 29, 1999
    Date of Patent: May 22, 2001
    Assignee: Shell Oil Company
    Inventors: Jozef Jacobus Titus Smits, Judith Johanna Berendina Walhof
  • Patent number: 6107419
    Abstract: 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: Grant
    Filed: December 10, 1997
    Date of Patent: August 22, 2000
    Assignee: Shell Oil Company
    Inventors: Yoshikazu Kobayashi, Takaya Shinmura, Yojiro Yamamoto
  • Patent number: 6037425
    Abstract: 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: Grant
    Filed: November 21, 1996
    Date of Patent: March 14, 2000
    Assignee: Shell Oil Company
    Inventors: Takao Fukuzawa, Tetsuro Imura, Masayuki Ohta
  • Patent number: 6031012
    Abstract: 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: Grant
    Filed: October 27, 1998
    Date of Patent: February 29, 2000
    Assignee: Kaneka Corporation
    Inventors: Naoaki Nakanishi, Koji Himeno, Shintaro Komitsu
  • Patent number: 6001873
    Abstract: 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: Grant
    Filed: May 30, 1997
    Date of Patent: December 14, 1999
    Assignee: Chang Chun Plastics Co., Ltd.
    Inventors: Kuen Yuan Hwang, Hong-Hsing Chen, An Bang Duh, Chie-Yih Ju
  • Patent number: 6001954
    Abstract: 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: Grant
    Filed: February 6, 1998
    Date of Patent: December 14, 1999
    Assignee: Shell Oil Company
    Inventors: Jozef Jacobus Titus Smits, Judith Johanna Berendina Walhof
  • Patent number: 5998568
    Abstract: 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: Grant
    Filed: January 14, 1999
    Date of Patent: December 7, 1999
    Assignee: Reichhold, Inc.
    Inventors: Hildeberto Nava, Karin F. Nelson-Baron
  • Patent number: 5969036
    Abstract: 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: Grant
    Filed: June 20, 1997
    Date of Patent: October 19, 1999
    Assignee: The Dexter Corporation
    Inventor: Stephen M. Dershem
  • Patent number: 5955551
    Abstract: 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: Grant
    Filed: August 6, 1997
    Date of Patent: September 21, 1999
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Chi-Wen Frank Cheng, Mark Bryant
  • Patent number: 5912317
    Abstract: 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: Grant
    Filed: August 15, 1997
    Date of Patent: June 15, 1999
    Assignee: ANGUS Chemical Company
    Inventor: Gaoming Wu
  • Patent number: 5558939
    Abstract: 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: Grant
    Filed: July 28, 1995
    Date of Patent: September 24, 1996
    Assignee: Shell Oil Company
    Inventors: George C. Blytas, Arthur H. Hale
  • Patent number: 5391687
    Abstract: 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: Grant
    Filed: October 18, 1993
    Date of Patent: February 21, 1995
    Assignee: Hitachi Chemical Company Ltd.
    Inventors: Katsuji Shibata, Kazuhito Kobayashi, Nozomu Takano, Masami Arai, Ikuo Hoshi
  • Patent number: 5278260
    Abstract: 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: Grant
    Filed: October 13, 1992
    Date of Patent: January 11, 1994
    Assignee: Ciba-Geigy Corporation
    Inventors: Werner Schaffner, Dimiter Hadjistamov
  • Patent number: 5212261
    Abstract: 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: Grant
    Filed: December 17, 1990
    Date of Patent: May 18, 1993
    Assignee: Henkel Research Corporation
    Inventor: Thomas J. Stierman
  • Patent number: 5098964
    Abstract: 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: Grant
    Filed: January 31, 1991
    Date of Patent: March 24, 1992
    Assignee: Shell Oil Company
    Inventors: Ronald S. Bauer, Kailash C. B. Dangayach
  • Patent number: 5098965
    Abstract: 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: Grant
    Filed: January 31, 1991
    Date of Patent: March 24, 1992
    Assignee: Shell Oil Company
    Inventors: Ronald S. Bauer, Kailash C. B. Dangayach
  • Patent number: 5075386
    Abstract: 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: Grant
    Filed: April 12, 1990
    Date of Patent: December 24, 1991
    Assignee: Eastman Kodak Company
    Inventor: Jeffrey J. Vanderbilt
  • Patent number: 5028686
    Abstract: 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: Grant
    Filed: September 18, 1990
    Date of Patent: July 2, 1991
    Assignee: The Dow Chemical Company
    Inventors: Zeng-Kun Liao, Chun S. Wang
  • Patent number: 4877857
    Abstract: 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: Grant
    Filed: January 11, 1989
    Date of Patent: October 31, 1989
    Assignee: The Dow Chemical Company
    Inventors: Robert P. Shirtum, Elaine B. Darby
  • Patent number: 4831101
    Abstract: 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: Grant
    Filed: September 24, 1987
    Date of Patent: May 16, 1989
    Assignee: Rutgerswerke AG
    Inventors: Karl Jellinek, Bert Meier, Rolf Herzog, Gunter Reinsch
  • Patent number: 4795791
    Abstract: 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: Grant
    Filed: November 27, 1987
    Date of Patent: January 3, 1989
    Assignee: The Dow Chemical Company
    Inventors: Raymond A. Koenig, Gunter H. Haertel
  • Patent number: 4778863
    Abstract: 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: Grant
    Filed: August 13, 1987
    Date of Patent: October 18, 1988
    Assignee: The Dow Chemical Company
    Inventors: Chun S. Wang, Zeng-kun Liao
  • Patent number: 4769437
    Abstract: 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: Grant
    Filed: September 18, 1987
    Date of Patent: September 6, 1988
    Inventor: David H. Blount
  • Patent number: 4756787
    Abstract: 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: Grant
    Filed: November 6, 1987
    Date of Patent: July 12, 1988
    Assignee: Loctite Corporation
    Inventors: Kieran F. Drain, David J. Dunn
  • Patent number: 4751280
    Abstract: 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: Grant
    Filed: August 19, 1987
    Date of Patent: June 14, 1988
    Assignee: The Dow Chemical Company
    Inventors: Ha Q. Pham, Benny B. Gammill
  • Patent number: 4746725
    Abstract: 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: Grant
    Filed: February 25, 1987
    Date of Patent: May 24, 1988
    Assignee: General Electric Company
    Inventors: Thomas L. Evans, Niles R. Rosenquist, Edgar E. Bostick
  • Patent number: 4722983
    Abstract: 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: Grant
    Filed: December 8, 1986
    Date of Patent: February 2, 1988
    Assignee: Ciba-Geigy Corporation
    Inventors: Charles E. Monnier, Friedrich Stockinger
  • Patent number: 4722990
    Abstract: 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: Grant
    Filed: August 15, 1985
    Date of Patent: February 2, 1988
    Assignee: The Dow Chemical Company
    Inventors: Raymond A. Koenig, Guenter H. Haertel
  • Patent number: 4711911
    Abstract: 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: Grant
    Filed: December 22, 1986
    Date of Patent: December 8, 1987
    Inventor: David H. Blount
  • Patent number: 4684701
    Abstract: 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: Grant
    Filed: September 24, 1986
    Date of Patent: August 4, 1987
    Assignee: The Dow Chemical Company
    Inventors: Chun S. Wang, Robert L. Bowden, Wuu N. Chen
  • Patent number: 4661562
    Abstract: 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: Grant
    Filed: November 4, 1985
    Date of Patent: April 28, 1987
    Assignee: Ashland Oil, Inc.
    Inventor: Anil B. Goel
  • Patent number: 4624975
    Abstract: 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: Grant
    Filed: September 20, 1985
    Date of Patent: November 25, 1986
    Assignee: The Dow Chemical Company
    Inventor: Ha Q. Pham
  • Patent number: 4558116
    Abstract: 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: Grant
    Filed: March 4, 1985
    Date of Patent: December 10, 1985
    Assignee: The Dow Chemical Company
    Inventors: Walter L. Wernli, Robert P. Shirtum