Two Or More Phenolic Reactants Patents (Class 528/104)
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Patent number: 5362822Abstract: An adduct is prepared by reacting (A) a compound containing at least one epoxy group per molecule, with (B) a compound containing at least one epoxide reactive group per molecule selected from the group consisting of phenolic, thiol, secondary amine and carboxyl; wherein (i) when compound (A) is a polyepoxide, compound (B) contains a single epoxide reactive group per molecule; (ii) when compound (A) is a monoepoxide it is a monoglycidyl ether and compound (B) contains at least two epoxide reactive groups per molecule; and (iii) at least one of components (A) and (B) contains a rodlike mesogenic moiety. These adducts are useful in the preparation of polyurethanes.Type: GrantFiled: January 3, 1994Date of Patent: November 8, 1994Assignee: The Dow Chemical CompanyInventor: Robert E. Hefner, Jr.
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Patent number: 5360884Abstract: Glycidyl amines containing mesogenic moieties result in improved properties when cured. These amines are useful in coatings, adhesives, encapsulants, moldings, laminates, and the like.Type: GrantFiled: May 28, 1992Date of Patent: November 1, 1994Assignee: The Dow Chemical CompanyInventors: Robert E. Hefner, Jr., Jimmy D. Earls
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Patent number: 5356959Abstract: Epoxy resins obtainable by reactingA) a polyfunctional epoxide, which carries on average 1.5 to 2.5 epoxy groups per molecule and has an epoxide equivalent weight of from 100 to 2000, with based on 1 mol of epoxy groupsB) from 0.1 to 0.5 mol of an alkylphenol, the alkyl groups of which carry from 6 to 20 carbon atoms, andC) from 1 to 100 mmol of a polyoxyalkylenediol obtained from 1,2-propylene oxide, or of a copolymer obtained from 1,2-propylene oxide and other alkylene oxides, which has an average molecular weight of from 200 to 5000 and, on average, from 1 to 4 sulfonic acid groups bonded to methyl groups per molecule, and alsoD) from 0.2 to 0.3 mol of a diol, which isd1) a phenolic diol and/ord2) a polyoxyalkylenediol which has an average molecular weight of from 200 to 5000,with the proviso that the reaction product has an epoxide equivalent weight of from 1000 to 5000, can be converted to pigment resins suitable for electrodeposition coating and pigment pastes can then be prepared from said resins.Type: GrantFiled: July 27, 1993Date of Patent: October 18, 1994Assignee: BASF Lacke & Farben AktiengesellschaftInventors: Klaus Huemke, Christian Sinn
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Patent number: 5348635Abstract: A series of oligomeric adducts of diols and diepoxides are disclosed which are precursors of amine resins for use in electrodeposition coatings. The adducts are epoxide-alcohol addition products of a polyaromatic and/or a mono-aromatic diol and a polyaromatic bis-glycidyl ether, and/or a monoaromatic bis-glycidyl ether and/or an alkoxy arylene bis-glycidyl ether, thioether or amine. The coatings which include amine resin, cross linking agent, grind resin and pigment exhibit excellent corrosion resistance.Type: GrantFiled: February 3, 1993Date of Patent: September 20, 1994Assignee: BASF CorporationInventors: James A. Laugal, Glenn E. Martin, Donald L. St. Aubin, Gerald G. Wold
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Patent number: 5344899Abstract: A phenolic resin is represented by the formula (1) ##STR1## wherein R.sup.1 denotes a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, m denotes an integer of from 0 to 10 and n denotes 0, 1 or 2. A method for producing the phenolic resin involves reacting in the presence of an acid catalyst 3a,4,7,7a-tetrahydroindene and a phenol represented by the formula (2) ##STR2## wherein R.sup.1 denotes a hydrogen atom or an alkyl group having 1 to 4 carbon atoms and n denotes 0, 1 or 2. An epoxy resin composition for encapsulation contains: (a) a curable epoxy resin, (b) the above phenolic resin, (c) a curing promotor, and (d) an inorganic filler.Type: GrantFiled: February 16, 1993Date of Patent: September 6, 1994Assignee: Nippon Oil Co., Ltd.Inventors: Masami Enomoto, Susumu Kubota, Fumiaki Oshimi, Hitoshi Yuasa, Yutaka Otsuki
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Patent number: 5342904Abstract: Polymer modified adducts are prepared by (A) reacting (1) an epoxy resin having an average of more than one vicinal epoxide group with (2) a compound containing an average of two or more hydrogen atoms reactive with an epoxide group; and (B) partially vinylizing reacting the product from step (A); and (C) polymerizing the partially vinylized product from step (B) with (3) a polymerizable ethylenically unsaturated monomer; with the proviso that at least one of the components (1), (2) or (3) contain one or more mesogenic or rodlike moieties. These adducts are useful as epoxy resin curing agents.Type: GrantFiled: April 7, 1993Date of Patent: August 30, 1994Assignee: The Dow Chemical CompanyInventors: Robert E. Hefner, Jr., Jimmy D. Earls
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Patent number: 5340911Abstract: A method for producing a liquid crystalline polyester, which comprises reacting compounds of the following formulas: ##STR1## and a dicarboxylic acid of the following formula ##STR2## wherein R.sup.1 is a bivalent aromatic hydrocarbon group having from 6 to 18 C atoms as starting material, for polycondensation in a molten state.Type: GrantFiled: October 20, 1993Date of Patent: August 23, 1994Assignee: Mitsubishi Kasei CorporationInventors: Osamu Kishiro, Rie Shirahama, Yasuyuki Sakata, Hideaki Tanaka, Ken Honma
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Patent number: 5338782Abstract: A composition comprising a 1,2-dialkylidenecyclobutane such as 1,2-dimethylenecyclobutane, a polyimide such as a bismaleimide, an epoxy resin and a curing agent for the epoxy resin can be thermally cured to a tough polymer blend having a high glass transition temperature.Type: GrantFiled: May 27, 1993Date of Patent: August 16, 1994Assignee: Shell Oil CompanyInventor: Larry S. Corley
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Patent number: 5336702Abstract: An aqueous resin dispersion containing as an aqueous resin component a polyurethane-modified epoxy-polyamine resin comprising a reaction product of an epoxy group-containing polyurethane compound obtained by the reaction of a polyhydroxy compound having a number average molecular weight of 50 to 8,000, a polyisocyanate compound, and a compound containing one hydroxyl group and at least one alicyclic epoxy group in a molecule; a bisphenol compound; a bisphenol diglycidyl ether compound; and an active hydrogen-containing amine compound. Said aqueous resin dispersion has excellent corrosion resistance and is suited especially for cathode electro-deposition coating.Type: GrantFiled: December 3, 1992Date of Patent: August 9, 1994Assignee: Kansai Paint Co., Ltd.Inventor: Koji Kamikado
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Patent number: 5312878Abstract: A thermosetting resin composition comprising (A) a naphthalene ring-bearing epoxy resin, (B) a dicyclopentadiene-modified phenolic resin, and (C) an inorganic filler is suitable for encapsulating semiconductor devices since the composition cures into a product having a low coefficient of expansion, good adhesion and low moisture absorption.Type: GrantFiled: October 1, 1992Date of Patent: May 17, 1994Assignee: Shin-Etsu Chemical Company, LimitedInventors: Toshio Shiobara, Kazutoshi Tomiyoshi, Takayuki Aoki, Hatsuji Shiraishi
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Patent number: 5310854Abstract: Advanced resin compositions are prepared from a compound having an average of more than one vicinal epoxide group per molecule and an epoxide equivalent weight of from about 170 to about 200 and a compound having an average of more than one aromatic hydroxyl group per molecule wherein the resultant advanced resin has an epoxide or aromatic hydroxyl equivalent weight of from about 200 to about 50,000.Type: GrantFiled: August 23, 1989Date of Patent: May 10, 1994Assignee: The Dow Chemical CompanyInventors: Ben W. Heinmeyer, Pong S. Sheih, David S. Wang
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Patent number: 5310859Abstract: A liquid crystalline polyester comprising dicarboxylic acid units of the following formula (1): ##STR1## wherein R.sup.1 is a bivalent aromatic hydrocarbon group having from 6 to 18 carbon atoms, diol units of the following formula (2):--OCH.sub.2 CH.sub.Type: GrantFiled: April 5, 1991Date of Patent: May 10, 1994Assignee: Mitsubishi Kasei CorporationInventors: Osamu Kishiro, Rie Shirahama, Yasuyuki Sakata, Hideaki Tanaka, Ken Honma
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Patent number: 5296570Abstract: Compositions comprising epoxy resins containing one or more rodlike mesogenic moieties per molecule are cured with polyamines containing one or more rodlike mesogenic moieties per molecule. These curable compositions can be oriented by the application of an electric field or magnetic field or drawing and/or shear flow prior to and/or during curing. The resultant cured products exhibit an improvement in one or more physical and/or mechanical and/or thermal properties as compared to a like epoxy resin system which does not contain any rodlike mesogenic moieties.Type: GrantFiled: June 1, 1993Date of Patent: March 22, 1994Assignee: The Dow Chemical CompanyInventors: Jimmy D. Earls, Robert E. Hefner, Jr., Paul M. Puckett
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Patent number: 5292831Abstract: Phenoxy resins containing rodlike mesogenic moieties are prepared from phenolic hydroxyl containing compounds which contain such moieties.Type: GrantFiled: July 27, 1992Date of Patent: March 8, 1994Assignee: The Dow Chemical CompanyInventors: Jimmy D. Earls, Robert E. Hefner, Jr., Paul M. Puckett
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Patent number: 5290887Abstract: Epoxy resins containing more than one vicinal epoxide group per molecule and at least one thiadiazole, oxadiazole or both thiadiazole and oxadiazole moiety per molecule are disclosed, as well as curable and cured compositions thereof. Certain of these epoxy resins possess enantiotropic liquid crystallinity. These enantiotropic epoxy resins are useful in preparing copolymers with high glass transition temperatures and liquid crystalline morphology, which can result in enhanced unidirectional mechanical properties. These epoxy resins are useful in coating, casting, encapsulation, electronic or structural laminate or composite, filament winding or molding applications.Type: GrantFiled: April 30, 1993Date of Patent: March 1, 1994Assignee: The Dow Chemical CompanyInventors: Robert E. Hefner, Jr., Joseph A. Schomaker, Jimmy D. Earls
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Patent number: 5281675Abstract: Novel cyclic imino ether compositions containing one or more mesogenic moieties, when polymerized, result in products having improved properties.Type: GrantFiled: February 6, 1992Date of Patent: January 25, 1994Assignee: The Dow Chemical CompanyInventors: Robert E. Hefner, Jr., Jimmy D. Earls
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Patent number: 5278259Abstract: An epoxy resin composition comprising:(A) as a resin chief material a bisphenol A type epoxy resin having the following formula (1), ##STR1## wherein n is 0 to 10, R.sup.1 and R.sup.2 each represents a glycidyl group, and A.sup.1 to A.sup.8 each represents a hydrogen atom or a bromine atom;(B) as an epoxy resin curing agent,(b1) a bisphenol A or a brominated product thereof having formula (1) (wherein n is 0, R.sup.1 and R.sup.2 each represents a hydrogen atom, and A.sup.1 to A.sup.4 each represents a hydrogen atom or a bromine atom), or(b2) a novolac resin of a bisphenol A or a brominated product thereof that is obtained by linking two or more molecules of a bisphenol A or a brominated product thereof having formula (1) (wherein n is 0, R.sup.1 and R.sup.2 each represents a hydrogen atom, and A.sup.1 to A.sup.4 each represents a hydrogen atom or a bromine atom), through a methylene group(s) at any of A.sup.1 to A.sup.Type: GrantFiled: April 12, 1991Date of Patent: January 11, 1994Assignee: Mitsubishi Denki Kabushiki KaishaInventors: Michio Futakuchi, Hiroyuki Nakajima, Takashi Takahama
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Patent number: 5275853Abstract: Polyetheramines having improved barrier to oxygen are thermoplastic polymers having aromatic ether/amine repeating units in their backbones and pendant hydroxyl moieties. Such polyetheramines are prepared by reacting diglycidyl ethers of dihydric aromatic compounds such as the diglycidyl ether of bisphenol-A, hydroquinone, or resorcinol with amines having no more than two amine hydrogens per molecule, such as piperazine or ethanolamine.Type: GrantFiled: April 7, 1992Date of Patent: January 4, 1994Assignee: The Dow Chemical CompanyInventors: H. Craig Silvis, Jerry E. White
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Patent number: 5273792Abstract: The present invention is directed to a novel epoxy polymeric composition resulting from reacting (A) at least one compound containing an average of more than one epoxide group per molecule with (B) at least one curing agent for component (A). At least a portion of the curing agent (B) is at least a first curing agent compound which contains (a) an average of more than one active amine hydrogen atom per molecule and (b) an average of at least one aromatic ring which contains at least one pendant monovalent electron withdrawing group. The present invention also includes a process for preparing the above polymeric materials. The polymeric materials of the present invention also exhibit nonlinear optical capabilities when formed into an optically transparent medium with a noncentrosymmetric alignment of molecules. The nonlinear optical materials of the present invention are useful in electrooptic devices for use in communications and data-processing.Type: GrantFiled: March 13, 1992Date of Patent: December 28, 1993Assignee: The Dow Chemical CompanyInventor: John J. Kester
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Patent number: 5270405Abstract: Advanced epoxy resins containing mesogenic moieties are prepared from epoxy resins which contain such moieties.Type: GrantFiled: July 27, 1992Date of Patent: December 14, 1993Assignee: The Dow Chemical CompanyInventors: Jimmy D. Earls, Robert E. Hefner, Jr., Paul M. Puckett
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Patent number: 5270406Abstract: Advanced epoxy resin compositions are prepared by reacting epoxy resins with active hydrogen-containing compounds which contain mesogenic moieties. Curable compositions containing these advanced epoxy resin compositions are useful in adhesives, coatings, laminates castings and the like.Type: GrantFiled: September 15, 1992Date of Patent: December 14, 1993Assignee: The Dow Chemical CompanyInventors: Jimmy D. Earls, Paul M. Puckett, Robert E. Hefner, Jr.
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Patent number: 5270404Abstract: Compositions comprising epoxy resins containing one or more rodlike mesogenic moieties per molecule are cured with curing agents which will normally cure epoxy resins. These curable compositions can be oriented by the application of an electric field, magnetic field drawing and/or shear flow prior to and/or during curing. The resultant cured products exhibit an improvement in one or more physical or mechanical properties as compared to a like epoxy resin system which does not contain any rodlike mesogenic moieties.Type: GrantFiled: July 17, 1992Date of Patent: December 14, 1993Assignee: The Dow Chemical CompanyInventors: Jimmy D. Earls, Robert E. Hefner, Jr., Paul M. Puckett
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Patent number: 5268434Abstract: An epoxy resin composition useful as a molded article is curable with a combination of curing agents including diamino-alpha-alkylstilbenes and other curing agents wherein the epoxy resin and/or the other curing agents can contain rodlike mesogenic moieties.Type: GrantFiled: January 5, 1993Date of Patent: December 7, 1993Assignee: The Dow Chemical CompanyInventors: Robert E. Hefner, Jr., Jimmy D. Earls
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Patent number: 5268435Abstract: A polyol resin substantially free of epoxy groups is useful as a coating material and is prepared by(i) reacting a bisphenol epoxy resin with a compound having one active hydrogen per molecule and optionally a bisphenol to form a polyol resin having secondary hydroxyl groups, and(ii) esterifying part of the secondary hydroxyl groups with a lactone or a monocarboxylic acid (ester) to form a polyol resin with graft-polymerized polyester moieties.Type: GrantFiled: June 12, 1991Date of Patent: December 7, 1993Assignees: Mitsui Petrochemical Industries, Ltd., Ricoh Company, Ltd.Inventors: Hideo Nakamura, Masaru Wakizaka, Yohzoh Yamamoto
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Patent number: 5266661Abstract: Curable compositions are disclosed which contain (I) an advanced resin composition prepared by reacting epoxy resins with active hydrogen-containing compounds which contain mesogenic moieties and (II) a suitable curing agent.Type: GrantFiled: September 15, 1992Date of Patent: November 30, 1993Assignee: The Dow Chemical CompanyInventors: Jimmy D. Earls, Paul M. Puckett, Robert E. Hefner, Jr.
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Patent number: 5266660Abstract: Compositions comprising epoxy resins containing one or more rodlike mesogenic moieties per molecule are cured with curing agents which will normally cure epoxy resins. These curable compositions can be oriented by the application of an electric field, magnetic field drawing and/or shear flow prior to and/or during curing. The resultant cured products exhibit an improvement in one or more physical or mechanical properties as compared to a like epoxy resin system which does not contain any rodlike mesogenic moieties.Type: GrantFiled: July 17, 1992Date of Patent: November 30, 1993Assignee: The Dow Chemical Co.Inventors: Robert E. Hefner, Jr., Jimmy D. Earls, Paul M. Puckett
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Patent number: 5266365Abstract: The present invention is directed to an epoxy-containing polymeric material having nonlinear optical properties, particularly a glycidyl amine polymer, and a process for making the nonlinear optical (NLO) epoxy-containing polymeric material including poling the polymeric material under high voltage at elevated temperature for a period of time to bring about orientation of the nonlinear optical functionalities in the polymer. The polymers have enhanced thermal stability and good NLO properties.Type: GrantFiled: February 28, 1992Date of Patent: November 30, 1993Assignee: The Dow Chemical CompanyInventors: John J. Kester, H. Craig Silvis
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Patent number: 5244998Abstract: Advanced resins and unadvanced epoxy resins are disclosed wherein the unadvanced compound and at least a portion of the advanced epoxy resin contains at least one --O--R.sup.1 --O-- or --(O--CH.sub.2 --CHR.sup.2).sub.n --O-- group as a bridge between two groups selected independently from the group consisting of (1) a saturated or unsaturated cycloaliphatic group, (2) an aromatic group, (3) a group represented by the formula ##STR1## or (4) a group represented by the formula ##STR2## Also disclosed are nucleophilic derivatives thereof, as well as curable compositions and coating compositions containing the advanced or unadvanced epoxy resins or nucleophilic modified advanced or unadvanced epoxy resins. These advanced resins and unadvanced epoxy resins provide coatings with good flexibility or formability as exhibited by good flexural or formable properties determined by reverse impact, T-bend and wedge-bend tests, chip resistance, and with good corrosion resistance and throwpower.Type: GrantFiled: June 17, 1992Date of Patent: September 14, 1993Assignee: The Dow Chemical CompanyInventors: Robert A. Dubois, Allyson Malzman, Pong S. Sheih, Alan R. Whetten
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Patent number: 5227453Abstract: High solids coating compositions are made from organic solvent solutions of the reaction product of a diglycidyl ether of a dihydric phenol, vernonia oil and a dihydric phenol.Type: GrantFiled: February 10, 1992Date of Patent: July 13, 1993Assignee: Hi-Tek Polymers, Inc.Inventors: Jim D. Elmore, William J. DeGooyer, Mary B. Tipton, John H. Kaiser
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Patent number: 5227452Abstract: Compositions comprising epoxy resins containing one or more rodlike mesogenic moieties per molecule are cured with polyamines containing one or more rodlike mesogenic moieties per molecule. These curable compositions can be oriented by the application of an electric field or magnetic field or drawing and/or shear flow prior to and/or during curing. The resultant cured products exhibit an improvement in one or more physical and/or mechanical and/or thermal properties as compared to a like epoxy resin system which does not contain any rodlike mesogenic moieties.Type: GrantFiled: June 29, 1992Date of Patent: July 13, 1993Assignee: The Dow Chemical CompanyInventors: Jimmy D. Earls, Robert E. Hefner, Jr., Paul M. Puckett
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Patent number: 5223558Abstract: A process for preparing an epoxy dimer acid ester resin, which comprises reacting (a) an epoxy resin which is a glycidyl ether of a dihydric phenol having a weight average molecular weight of 1,000 to 30,000 and an epoxy equivalent of 300 to 5,000 with (b) a dimer acid in the presence of an organic solvent having an alcoholic hydroxyl group at a concentration such that the solid content of both reactants (a) and (b) ranges from 60 to 90 percent by weight based on the total weight of the reaction mixture. An epoxy dimer acid ester resin prepared by the process and a coating therefrom are also disclosed. The coating is particularly useful for coating a coil of a steel sheet.Type: GrantFiled: July 15, 1992Date of Patent: June 29, 1993Assignee: The Dow Chemical CompanyInventor: Kaoru Ohba
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Patent number: 5218061Abstract: The present invention relates to a novel polyfunctional epoxy resin having two phenolic glycidyl ether groups, one or more of alcoholic glycidyl ether groups and one or more of alcoholic hydroxyl groups in one molecules. The present invention further provides an epoxy resin composition comprising the epoxy resin. The cured product obtained from the epoxy resin composition according to the present invention is excellent in heat resistance, toughness, adhesion property and water proofness, and it is extremely useful for a wide range of application uses such as molding materials, casting materials, laminate materials, coating materials, adhesives and photoresists.Type: GrantFiled: September 10, 1991Date of Patent: June 8, 1993Assignee: Nippon Kayaku Kabushiki KaishaInventors: Yoshitaka Kajiwara, Shoushi Takahashi, Kenichi Mizoguchi, Sumio Saito
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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: 5194560Abstract: A series of oligomeric adducts of diols and diepoxides are disclosed which are precursors of amine resins for use in electrodeposition coatings. The adducts are epoxide-alcohol addition products of a polyaromatic and/or a mono-aromatic diol and a polyaromatic bis-glycidyl ether, and/or a monoaromatic bis-glycidyl ether and/or an alkoxy arylene bis-glycidyl ether, thioether or amine. The coatings which include amine resin, cross linking agent, grind resin and pigment exhibit excellent corrosion resistance.Type: GrantFiled: March 21, 1991Date of Patent: March 16, 1993Assignee: BASF CorporationInventors: James A. Laugal, Glenn E. Martin, Donald L. St. Aubin, Gerald G. Wold
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Patent number: 5191033Abstract: The invention is an epoxy resin composition. Diol initiators are reacted with alkylene oxide and 1 to 5 wt % epoxy resin. The epoxy resin is added internally, along the length of the diol chain to yield a modified polyol of molecular weight 2000 to 5000. The modified polyol is subjected to reductive amination to yield a polyamine. This polyamine is mixed with an epoxy base resin and cured to product epoxy resins demonstrating improved strength and adhesion.Type: GrantFiled: May 11, 1992Date of Patent: March 2, 1993Assignee: Texaco Chemical CompanyInventors: Michael Cuscurida, George P. Speranza, Kathy B. Sellstrom
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Patent number: 5166184Abstract: A normally liquid epoxy resin obtainable by reaction of a bisphenol based oligocarbonate having terminal phenolic hydroxyl groups with an epihalohydrin, followed by dehydrohalogenation. The epoxy resin is capable of forming a tough cured product having improved flexural strength and flexural modulus. A process for the production of an epoxy resin foam in which a polyepoxy compound is crosslinked and simultaneously foamed by the aid of carbonate oligomers having terminal phenolic hydroxyl groups. The product is highly flexible against compression, bending and warp.Type: GrantFiled: April 24, 1992Date of Patent: November 24, 1992Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Michio Hashimoto, Taira Harada, Yoshihisa Kiso, Isao Kaneko, Gorou Suzuki
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Patent number: 5164472Abstract: Polyethers having improved barrier to oxygen are normally solid, thermoplastic polyethers having backbone repeating units of m-phenylene, p-phenylene, carbonyldiphenylene and/or sulfonyldiphenyl and pendent hydroxyl moieties. Such polyethers are prepared by reacting diglycidyl ethers of dihydric aromatic compounds such as the diglycidyl ether of bisphenol A with resorcinol.Type: GrantFiled: January 18, 1990Date of Patent: November 17, 1992Assignee: The Dow Chemical CompanyInventors: Jerry E. White, James W. Ringer
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Patent number: 5149768Abstract: Hydroxy-functional poly(ether sulfonamides) prepared by polymerizing an N,N'-dialkyl or N,N'-diaryldisulfonamide with a diepoxide in the presence of a suitable catalyst exhibit high barrier properties. These are suitable for use in the manufacture of articles such as rigid containers and flexible films exhibiting high barrier to oxygen.Type: GrantFiled: June 21, 1991Date of Patent: September 22, 1992Assignee: The Dow Chemical CompanyInventors: Jerry E. White, Anthony P. Haag, R. Garth Pews
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Patent number: 5147905Abstract: Advanced resins and unadvanced epoxy resins are disclosed wherein the unadvanced compound and at least a portion of the advanced epoxy resin contains at least one --O--R.sup.1 --O-- or --(O--CH.sub.2 --CHR.sup.2).sub.n --O-- group as a bridge between two groups selected independently from the group consisting of (1) a saturated or unsaturated cycloaliphatic group, (2) an aromatic group, (3) a group represented by the formula ##STR1## or (4) a group represented by the formula ##STR2## Also disclosed are nucleophilic derivatives thereof, as well as curable compositions and coating compositions containing the advanced or unadvanced epoxy resins or nucleophilic modified advanced or unadvanced epoxy resins. These advanced resins and unadvanced epoxy resins provide coatings with good flexibility or formability as exhibited by good flexural or formable properties determined by reverse impact, T-bend and wedge-bend tests, chip resistance, and with good corrosion resistance and throwpower.Type: GrantFiled: May 1, 1991Date of Patent: September 15, 1992Assignee: The Dow Chemical CompanyInventors: Robert A. Dubois, Duane S. Treybig, Allyson Malzman, Pong S. Sheih, Alan R. Whetten
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Patent number: 5143998Abstract: Hydroxy-functional poly(amide-ethers) are fabricated into articles such as rigid containers and flexible films exhibiting high barrier to oxygen transmission in both dry and moist environments. For example, a polymer prepared by reacting the diglycidyl ether of 4,4'-isopropylidene bisphenol with .alpha.,.alpha.'-bis(4-hydroxybenzamido)-1,3-xylene exhibits especially high barrier.Type: GrantFiled: September 13, 1991Date of Patent: September 1, 1992Assignee: The Dow Chemical CompanyInventors: David J. Brennan, Anthony P. Haag, Jerry E. White
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Patent number: 5140079Abstract: The products resulting from contacting an organic phosphine or arsine with an inorganic acid having a weak nucleophilic anion provide for relatively stable compositions when admixed with a compound containing an average of more than one vicinal epoxide group per molecule and which optionally contains a compound containing an average of more than one phenolic hydroxyl group per molecule.Type: GrantFiled: April 15, 1991Date of Patent: August 18, 1992Assignee: The Dow Chemical CompanyInventors: John W. Muskopf, Louis L. Walker, James L. Bertram
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Patent number: 5134218Abstract: Poly(hydroxy amide ethers) which exhibit high barrier properties are prepared by contacting one or more amide-containing bisphenols and an epihalohydrin. These polymers are suitable for use in the manufacture of articles such as rigid containers and flexible films exhibiting high barrier to oxygen transmission in moist environments.Type: GrantFiled: June 6, 1991Date of Patent: July 28, 1992Assignee: The Dow Chemical CompanyInventors: David J. Brennan, Jerry E. White
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Patent number: 5130350Abstract: Cathodic electrocoating binders which are water-dilutable on protonation with an acid are obtainable by reactingA) an epoxy compound or a mixture of epoxy compounds having an epoxide equivalent weight of less than 2,000 withB) a compound which is monofunctional with respect to epoxides and contains aliphatic or phenolic OH groups andC) a secondary amine of 2 to 36 carbon atoms, with the proviso that the reaction product of A), B) and C) still contains free epoxy groups, andD) an amount of an amidoamine containing primary amino groups which is equivalent to or greater than the amount of these free epoxy groups, the said amidoamine being obtainable from a primary diamine and a mono- and/or dicarboxylic acid.Type: GrantFiled: April 8, 1991Date of Patent: July 14, 1992Assignee: BASF Lacke & Farben AktiengesellschaftInventors: Thomas Schwerzel, Hans Schupp, Dirk Lawrenz, Hans Oslowski, Ulrich Heimann
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Patent number: 5115075Abstract: Polyethers having improved barrier to oxygen are normally solid, thermoplastic polyethers having aromatic ether repeating units in their backbones and pendent hydroxyl moieties and pendent amido, N-substituted amido and/or hydroxyalkyl moieties. Such polyethers are prepared by reacting diglycidyl ethers of dihydric aromatic compounds such as diglycidyl ether of bisphenol A with dihydric phenols having pendent amido, N-substituted amido and/or hydroxyalkyl moieties such as 2,2-bis(4-hydroxyphenyl)acetamide and 3,5-dihydroxybenzamide.Type: GrantFiled: May 8, 1990Date of Patent: May 19, 1992Assignee: The Dow Chemical CompanyInventors: David J. Brennan, Jerry E. White, Anthony P. Haag, Shari L. Kram
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Patent number: 5112934Abstract: The present invention is directed to an epoxy-containing polymeric material having nonlinear optical properties, particularly a glycidyl amine polymer, and a process for making the nonlinear optical (NLO) epoxy-containing polymeric material including poling the polymeric material under high voltage at elevated temperature for a period of time to bring about orientation of the nonlinear optical functionalities in the polymer. The polymers have enhanced thermal stability and good NLO properties.Type: GrantFiled: November 27, 1989Date of Patent: May 12, 1992Assignee: The Dow Chemical CompanyInventors: John J. Kester, H. Craig Silvis
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Patent number: 5091474Abstract: A two component-type curing agent composition is disclosed which comprises a first curing agent which is capable of cross-linking an epoxy resin and which is at least one member selected from primary amines, phenolic compounds and acid anhydrides, and a second curing agent which is at least one compounds represented by the following general formula: ##STR1## wherein X is --CR.sub.1 R.sub.2 --, --CO--, --COO--, --SO.sub.2 --, --SO--, --S--, --O--, --NR.sub.1 --, --SiR.sub.1 R.sub.2 -- or --POR.sub.1 -- where R.sub.1 and R.sub.2 each stands for hydrogen, a lower alkyl or a phenyl; Y and Y' each stands for hydrogen, a lower alkyl or an electron attracting group; R is a lower alkyl; and m and n each is an integer of 1-4.Type: GrantFiled: January 18, 1991Date of Patent: February 25, 1992Assignee: Toa Nenryo Kogyo Kabushiki KaishaInventors: Shinkichi Murakami, Osamu Watanabe, Sadahisa Wada, Makoto Miyazaki, Hiroshi Inoue
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Patent number: 5089588Abstract: Hydroxy-functional poly(amide-ethers) are fabricated into articles such as rigid containers and flexible films exhibiting high barrier to oxygen transmission in both dry and moist environments. For example, a polymer prepared by reacting the diglycidyl ether of 4,4'-biphenol with N,N'-bis(m-hydroxyphenyl)-adipamide exhibits especially high barrier.Type: GrantFiled: February 26, 1991Date of Patent: February 18, 1992Assignee: The Dow Chemical CompanyInventors: Jerry E. White, David J. Brennan, Steven Pikulin
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Patent number: 5086094Abstract: Nonaqueous organic solvent solutions of phosphate esters of epoxy resins. Coating compositions containing these compositions have improved thermal properties as compared to like compositions which are dispersed in water.Type: GrantFiled: May 29, 1990Date of Patent: February 4, 1992Assignee: The Dow Chemical CompanyInventor: John L. Massingill, Jr.
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Patent number: 5070174Abstract: Disclosed in a polyamide epoxy ester resin having a weight average molecular weight of 1,000 to 100,000, an epoxy equivalent of 500 to 10,000, and an acid value of not greater than 10, which is prepared by reacting(i) at least one epoxy resin which is a glycidyl ether of a dihydric phenol,(ii) at least one dihydric phenol and(iii) a polyamide dicarboxylic acid having an amine value of not greater than 20 and an acid value of at least 20, which is prepared by reacting a polymerized fatty acid composed mainly of a dimer acid with a diamine at a polymerized fatty acid/diamine molar ratio of from 2/1.0 to 2/1.9,at a ratio of such that the amount of the polyamide dicarboxylic acid segment in the resin ranges 1 to 30 percent by weight based on the weight of the resin.Also, disclosed are a process for preparing the polyamide epoxy ester resin and a coating composition comprising the resin. The coating composition is particularly useful for can coating.Type: GrantFiled: December 31, 1990Date of Patent: December 3, 1991Assignee: The Dow Chemical CompanyInventor: Kaoru Ohba
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Patent number: 5068268Abstract: New epoxy polymers comprise lightly crosslinked linear molecules prepared from segments containing stiff units interconnected to form internally non-rotating, planar segments.Type: GrantFiled: September 12, 1989Date of Patent: November 26, 1991Assignee: Shell Oil CompanyInventor: Kenneth C. Dewhirst