Mixed With An 1,2-epoxy-containing Chemical Treating Agent Patents (Class 525/507)
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Patent number: 5077375Abstract: A glycidyl ether of a phenolic compound of the formula: ##STR1## wherein each of R.sup.1 through R.sup.6 represents an alkyl group of from 1 to 6 carbon atoms; each of R.sup.7 to R.sup.12 represents a hydrogen atom, an alkyl group of from 1 to 4 carbon atoms, or an alkoxy group of from 1 to 4 carbon atoms; X represents a chlorine or bromine atom; GE represents a glycidyl ether group; a, b, c, d, and e are 0 or 1; and n is an average number of from 0.5 to 5. The high purity glycidyl ether of the phenolic compound can be produced by reacting the corresponding phenolic compound with an epichlorohydrin in an aprotic polar solvent in the presence of an alkali metal hydroxide and then treating the resulting crude glycidyl ether compound with an alkaline material in an organic solvent.Type: GrantFiled: January 22, 1991Date of Patent: December 31, 1991Assignee: Sumitomo Chemical Company, LimitedInventors: Noriaki Saito, Shuichi Kanagawa, Hideshi Sakamoto
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Patent number: 5049628Abstract: The present invention relates to an unsaturated group-containing polycarboxylic acid resin produced by reacting an epoxidized compound of a condensate of a phenolic compound and an aromatic aldehyde having a phenolic hydroxyl group with (meth)acrylic acid, and further reacting the reaction product with polybasic carboxylic acid or an anhydride thereof; a composition comprising the resin and a cured product of the resin or the composition.The composition according to the present invention is developable with an aqueous alkaline solution and suitable for a solder resist composition which is excellent in heat resistance, solvent resistance, adhesion, electric insulation property and storage stability.Type: GrantFiled: September 27, 1989Date of Patent: September 17, 1991Assignee: Nippon Kayaku Kabushiki KaishaInventors: Kazuyoshi Nawata, Tetsuo Ohkubo, Minoru Yokoshima
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Patent number: 5041358Abstract: A composition containing a polymeric material obtained by interreacting an epoxy-novolak polymer with an organosilicon compound, a radiation sensitive onium salt, and a near U.V. sensitizer.Type: GrantFiled: April 17, 1989Date of Patent: August 20, 1991Assignee: International Business Machines CorporationInventors: Michael Hatzakis, Jane M. Shaw, Kevin J. Stewart
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Patent number: 5039450Abstract: A process for the separation of crude oil emulsions of the water-in-oil typeIn the novel process addition products made from certain ethylene oxide/propylene oxide block polymers and certain polyglycidyl ethers of phenol/formaldehyde condensation products are added to the crude oil emulsions.Type: GrantFiled: March 16, 1989Date of Patent: August 13, 1991Assignee: Hoechst AktiengesellschaftInventors: Rainer Kupfer, Willibald Bose, Martin Hille, Roland Bohm, Friedrich Staiss
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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: 5011904Abstract: Epoxy-containing compounds are prepared by dehydrohalogenating the reaction product of an epihalohydrin with the reaction product of a compound containing an average of more than one aromatic hydroxyl group per molecule with an alkylene oxide wherein the ratio of moles of epihalohydrin to hydroxyl groups is at least about 1.2:1. When these epoxy containing compounds are formulated into coatings, the resultant products have improved chemical resistance to acids.Type: GrantFiled: November 20, 1989Date of Patent: April 30, 1991Assignee: The Dow Chemical CompanyInventors: Michael B. Cavitt, Dennis L. Steele, David J. Duncan
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Patent number: 5008350Abstract: A glycidyl ether of a phenolic compound of the formula: ##STR1## wherein each of R.sup.1 through R.sup.6 represents an alkyl group of from 1 to 6 carbon atoms; each of R.sup.7 to R.sup.12 represents a hydrogen atom, an alkyl group of from 1 to 4 carbon atoms, or an alkoxy group of from 1 to 4 carbon atoms; X represents a chlorine or bromine atom ; GE represents a glycidyl ether group; a, b, c, d, and e are 0 or 1; and n is an average number of from 0.5 to 5. The high purity glycidyl ether of the phenolic compound can be produced by reacting the corresponding phenolic compound with an epichlorohydrin in an aprotic polar solvent in the presence of an alkali metal hydroxide and then treating the resulting crude glycidyl ether compound with an alkaline material in an organic solvent.Type: GrantFiled: December 12, 1988Date of Patent: April 16, 1991Assignee: Sumitomo Chemical Company, LimitedInventors: Noriaki Saito, Shuichi Kanagawa, Hideshi Sakamoto
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Patent number: 5003025Abstract: The invention relates to water-dilutable binders for cationic electrocoating finishes. For the preparation of the binders, a di-epoxide compound, together with at least one mono-epoxide compound if desired, is converted by a polyaddition, carried out at 100.degree. to 195.degree. C. and initiated by a monofunctionally reacting initiator carrying either an alcoholic OH group, a phenolic OH group or an SH group, to form an epoxy resin which then subsequently is modified with(A) primary and/or secondary amines or their salts and/or the salt of a tertiary amine, a sulfide/acid mixture or a phosphine/acid mixture and with, if desired,(B) a polyfunctional alcohol, a polycarboxylic acid, a polysulfide or a polyphenol.Type: GrantFiled: December 20, 1989Date of Patent: March 26, 1991Assignee: BASF Lacke & Farben AktiengesellschaftInventors: Arnold Dobbelstein, Michael Geist, Gunther Ott, Georg Schon
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Patent number: 5001174Abstract: An epoxy resin composition for semiconductor sealing which comprises, as essential components,(A) an epoxy resin comprising 50-100% by weight, based on total epoxy resin amount, of a polyfunctional epoxy resin represented by the formula (I) ##STR1## wherein n and m are each an integer of 0 or more, n+m=1-10, and R.sub.1, R.sub.2 and R.sub.3 which may be the same or different, are each selected from hydrogen atom, an alkyl group and a halogen atom, with the proviso that all of R.sub.1, R.sub.2 and R.sub.3 must not be hydrogen atom simultaneously,(B) a phenolic resin curing agent,(C) a silica filler, and(D) a curing accelerator.Type: GrantFiled: December 4, 1989Date of Patent: March 19, 1991Assignee: Sumitomo Bakelite Company LimitedInventors: Kenichi Yanagisawa, Naoki Mogi, Hironori Ohsuga, Hiroshi Shimawaki
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Patent number: 4965324Abstract: The 2-functional component of substituted phenol-aldehyde novolac resins is reduced. Epoxy novolac resins prepared from the novolac resin containing reduced quantities of 2-functional product exhibit increased Tg values when cured.Type: GrantFiled: November 17, 1989Date of Patent: October 23, 1990Assignee: The Dow Chemical CompanyInventors: James L. Bertram, Louis L. Walker, Avis L. McCrary, Fermin M. Cortez
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Patent number: 4962162Abstract: The resin composition which contains thermosetting resin as Component (A), a thermoplastic resin as Component (B), and at least one compound selected from the group consisting of an epoxy resin capable of dissolving the thermoplastic resin and a reactive diluent possessing at least one epoxy group as Component (C) in a ratio such that the proportions of Components (A), (B), and (C) fall respectively in the ranges of 30 to 96% by weight, 2 to 50% by weight, and 2 to 49% by weight, based on the total weight of the resin composition. The resin composition is capable of producing a molded article combining the highly satisfactory mechanical and thermal properties of a thermosetting resin and the highly satisfactory toughness of a thermoplastic resin.Type: GrantFiled: September 30, 1987Date of Patent: October 9, 1990Assignee: Toho Rayon Co., Ltd.Inventors: Hiroyuki Kosuda, Yasuhisa Nagata, Masato Andoh
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Patent number: 4954583Abstract: Novel 1-arylcyclobutenecarboxylate esters of glycidyloxy compounds having at least two glycidyloxy substituents are self-curing thermoset resins. The cured products derived by applying heat to the esters are crosslinked insoluble solids having good properties.Type: GrantFiled: June 12, 1989Date of Patent: September 4, 1990Assignee: Shell Oil CompanyInventor: Pen-Chung Wang
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Patent number: 4954584Abstract: Thermosetting resin compositions comprise a mixture of a 1-arylcyclobutenecarboxylate ester of a glycidyloxy compound having at least two glycidyloxy substituents and at least one polymerizable monomer having at least two substituents with multiple valence bonds between adjacent atoms. Also claimed are the cured products obtained by heating such compositions.Type: GrantFiled: June 12, 1989Date of Patent: September 4, 1990Assignee: Shell Oil CompanyInventor: Pen-Chung Wang
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Patent number: 4952646Abstract: Epoxy resins can be cured by the use of a curing agent formed by the reaction of phosphorus pentoxide with a trialkyl phosphate or phosphonate.Type: GrantFiled: July 20, 1989Date of Patent: August 28, 1990Assignee: Akzo America Inc.Inventors: Edward D. Weil, John Tomko, Fred Jaffe
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Patent number: 4945138Abstract: Vinyl ester resins of substituted epoxidized hydroxystyrylaza compounds are disclosed. These vinyl esters may be combined with various reactive monomers, prepolymers or polymers and cured to give a combination of high mechanical strength and glass transition temperature.Type: GrantFiled: February 28, 1989Date of Patent: July 31, 1990Assignee: The Dow Chemical CompanyInventors: Robert E. Hefner, Jr., John W. Robinson
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Patent number: 4933259Abstract: A composition useful as an alkaline developable liquid photoimageable solder resist ink comprising a photocurable resin, a photopolymerization initiator, a reactive diluent, a solvent and optionally, a thermosetting material as main components wherein the photocurable resin comprises a reaction product of: (A) an epoxy vinyl ester resin obtained by reacting a cresol novolak epoxy resin and an unsaturated monobasic acid, (B) a polybasic acid anhydride and (C) an alkyl ketene dimer, wherein the hydroxyl value of the photocurable resin is not more than 10 carbons. Coating films formed from the subject composition have excellent adhesion, heat resistance, moisture insulation resistance and alkaline developable properties.Type: GrantFiled: August 24, 1988Date of Patent: June 12, 1990Assignee: Arakawa Chemical Industries, Ltd.Inventors: Machio Chihara, Mitsukazu Funahashi
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Patent number: 4931515Abstract: An epoxy resin composition comprising a novolak type epoxy resin which is produced from a substituted-phenol novolak and epihalohydrin, and is 0.15 or less in a maximum absorbance of a 3% (W/V) dichloromethane solution of the epoxy resin, the absorbance being measured at a wave number of between 3570 and 3600 cm.sup.-1 with an infrared spectrophotometer having a cell of 2 mm length, which is useful particularly in encapsulating and laminating applications in electronic fields.Type: GrantFiled: December 8, 1988Date of Patent: June 5, 1990Assignee: Sumitomo Chemical Company, LimitedInventors: Hisao Takagishi, Shuichi Kanagawa, Kunimasa Kamio, Kazuo Sumiyoshi
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Patent number: 4925901Abstract: Storage stable compositions are disclosed which comprise an epoxide containing compound, a phenolic hydroxyl containing compound, and a catalyst compound for catalyzing the reaction between epoxide groups and aromatic hydroxyl groups which catalyst comprises the product resulting from contacting an onium salt, amine, or amine salt with an acid or a salt of an acid having a weak nucleophilic anion.Type: GrantFiled: November 18, 1988Date of Patent: May 15, 1990Assignee: The Dow Chemical CompanyInventors: James L. Bertram, Louis L. Walker, John W. Muskopf
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Patent number: 4920182Abstract: Compositions are described containing(A) an epoxy resin having on average at least two 1,2-epoxy groups per molecule or a mixture of these epoxy resins,(B) a compound of the formula I or a mixture of these compounds ##STR1## in which a and b independently of one another are 1 or 2, R.sup.1 is a .pi.-arene, R.sup.2 is a .pi.-arene, an indenyl anion or a cyclopentadienyl anion, X.sup..crclbar. is an [LQ.sub.m ].sup..crclbar. or an anion of a partially fluorinated or perfluorinated aliphatic or aromatic sulfonic acid, L is B, P, As or Sb, Q is fluorine or some of the radicals Q can also be hydroxyl groups and m corresponds to the valence of L increased by one, and(C) a flexible polyester which is terminated by, on average, at least two carboxyl groups and which is derived from an aliphatic or cycloaliphatic polyol or a mixture of such polyols and from an aliphatic, cycloaliphatic or aromatic polycarboxylic acid or a mixture of such polycarboxylic acids.Type: GrantFiled: December 5, 1988Date of Patent: April 24, 1990Assignee: Ciba-Geigy CorporationInventors: Aloysius H. Manser, Dieter Strasilla, Rolf Mulhaupt
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Patent number: 4882216Abstract: A film comprising a metal foil and a flexible epoxy resin layer covered therewith, wherein the flexible epoxy resin layer is formed from a flexible epoxy resin composition containing one or more polythiol compounds as a hardener, and a flexible printed wiring board produced therefrom.Type: GrantFiled: August 9, 1988Date of Patent: November 21, 1989Assignee: Kashima Industries Co.Inventors: Hideo Takimoto, Katsuji Tokuda, Koji Yamamoto
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Patent number: 4880892Abstract: Advancement catalysts which are a combination of a phosphonium halide or an alkylene phosphorane and a nitrogen heterocycle selected from the group consisting of substituted or unsubstituted imidazoles, benzimidazoles, imidazolines, dihydropyrimidines, tetrahydropyrimidines, dihydroquinazolines, their salts and mixtures thereof, confer high reactivity and selectivity on epoxy resin advancement reactions. The advanced epoxy resins are useful in the preparation of coatings of high quality.Type: GrantFiled: August 22, 1988Date of Patent: November 14, 1989Assignee: Ciba-Geigy CorporationInventors: Wataru Urano, Yasuaki Sugano
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Patent number: 4877859Abstract: The present invention provides a fluroine-containing novolak resin or its derivative having a repeating unit of the formula ##STR1## wherein R.sup.1 is hydrogen atom, OH or ##STR2## R.sup.2 is hydrogen atom or alkyl group having 1 to 4 carbon atoms, X is fluorine-containing monovalent organic group having 2 to 20 carbon atoms.The present invention also provides a perfluoroalkenyloxphenol or its derivative of the formula ##STR3## wherein R.sup.10 is OH or ##STR4## R.sup.11 is H, OH, alkyl group having 1 to 4 carbon atoms or ##STR5## Y is perfluoroalkenyl group having 6 to 14 carbon atoms.Type: GrantFiled: March 21, 1988Date of Patent: October 31, 1989Assignee: Daikin Industries, Ltd.Inventors: Sinji Tamaru, Motonobu Kubo, Masato Kashiwagi
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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: 4855366Abstract: A low viscosity product is obtained when an adduct is prepared by reacting (A) at least one polyglycidyl ether of a compound containing an average of more than one phenolic hydroxy group per molecule and (B) at least one aliphatic monocarboxylic acid containing 7 to 15 carbon atoms per molecule; wherein components (A) and (B) are present in amounts which provide a ratio of carboxylic acid groups per epoxide group of from about 0.01:1 to about 0.2:1.Type: GrantFiled: June 22, 1988Date of Patent: August 8, 1989Assignee: The Dow Chemical CompanyInventor: Michael B. Cavitt
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Patent number: 4855339Abstract: An epoxy resin composition comprising (A) an epoxy resin having three or more epoxy groups per a molecule and (B) a reactive oligomer having in its molecule an aromatic residue connected thereto by --O-- or --S-- linkage and having at the terminal of the molecule a phonolic hydroxyl group.Type: GrantFiled: January 19, 1989Date of Patent: August 8, 1989Assignee: Sumitomo Chemical Company, LimitedInventors: Yasuhisa Saito, Hisao Takagishi, Hiroshi Nakamura, Kohichi Okuno, Yutaka Shiomi, Kunimasa Kamio
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Patent number: 4855367Abstract: Orthocarbonates of the formula I ##STR1## in which R is C.sub.1 -C.sub.4 alkyl, x is zero, 1 or 2, and A is a trivalent radical derived from an aliphatic triol by omitting the hydroxyl groups, the hydroxyl groups of the triol being bonded to different carbon atoms, are suitable as cocomponents in the curing of epoxy resins in that they limit the reduction in volume occurring during curing of epoxy resins. In addition, the cured resins are distinguished by increased flexural strength and impact strength.Type: GrantFiled: June 7, 1988Date of Patent: August 8, 1989Assignee: Giba-Geigy CorporationInventors: Peter Flury, Sameer H. Eldin, Martin Roth, Claus W. Rabener
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Patent number: 4851483Abstract: Vinyl ester resins of substituted epoxidized hydroxystyrylaza compounds are disclosed. These vinyl esters may be combined with various reactive monomers, prepolymers or polymers and cured to give a combination of high mechanical strength and glass transition temperature.Type: GrantFiled: September 25, 1987Date of Patent: July 25, 1989Assignee: The Dow Chemical CompanyInventors: Robert E. Hefner, Jr., John W. Robinson
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Patent number: 4851485Abstract: Non-fluorinated epoxy resins of a known type are cross-linked by means of polyfunctional fluoroalkanes containing groups which are reactive with the epoxy groups and/or with the hydroxy groups present in the starting resin. The cross-linked products so obtained, having a fluorine content not higher than 15% by weight, and preferably ranging from 1% to 5%, exhibit a complex of properties which are typical of the corresponding fluorinated resins having a much higher fluorine content; in particular, oil- and water-repellency, resistance to hydrolysis and to solvents, and minimum absorption of water.Type: GrantFiled: June 1, 1988Date of Patent: July 25, 1989Assignee: Ausimont S.p.A.Inventors: Alberto Re, Claudio Tonelli, Vito Tortelli
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Patent number: 4845171Abstract: A process for producing self-crosslinking cationic paint binders, water-dilutable upon protonation, on the basis of urea and urethane group carrying reaction products of modified phenols and monoepoxy compounds as well as with the binders produced according to this process and their use in stoving paints, particularly electrodeposition paints are described. The process is characterized in that a substituted urea-phenol-formaldehyde condensate obtained through reaction of an aminoalkylation product of a phenol, carrying an average of at least one secondary amino group with a semi-blocked diisocyanate, or a substituted urea prepared from a semi-blocked diisocyanate and an amine and further reacted with formaldehyde and a phenol, is reacted with a monoepoxy compound, the free aliphatic hydroxy groups of the reaction product being reacted in a further reaction step with di- or polyisocyanates. The paints formulated with these products, at stoving temperatures of from 150.degree. to 170.degree. C.Type: GrantFiled: December 3, 1987Date of Patent: July 4, 1989Assignee: Vianova Kunstharz, A.G.Inventors: Johann Gmoser, Willibald Paar, Michael Honel
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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: 4829134Abstract: An epoxy resin composition containing an oxazoline compound in an epoxy resin.Type: GrantFiled: August 11, 1987Date of Patent: May 9, 1989Assignee: Kabushiki Kaisha ToshibaInventors: Tsuguo Sakamoto, Kazuhiko Kurematsu, Yukihiro Mikogami, Shuichi Suzuki, Cao M. Thai
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Patent number: 4824927Abstract: The invention relates to water-dilutable binders for cationic electrocoating finishes. For the preparation of the binders, a di-epoxide compound, together with at least one mono-epoxide compound if desired, is converted by a polyaddition, carried out at 100.degree. to 195.degree. C. and initiated by a monofunctionally reacting initiator carrying either an alcoholic OH group, a phenolic OH group or an SH group, to form an epoxy resin which then subsequently is modified with(A) primary and/or secondary amines or their salts and/or the salt of a tertiary amine, a sulfide/acid mixture or a phosphine/acid mixture and with, if desired,(B) a polyfunctional alcohol, a polycarboxylic acid, a polysulfide or a polyphenol.Type: GrantFiled: January 23, 1987Date of Patent: April 25, 1989Assignee: BASF Lacke & Farben AKTInventors: Arnold Dobbelstein, Michael Geist, Gunther Ott, Georg Schon
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Patent number: 4814394Abstract: Polyethers with are suitable as oil demulsifiers are obtainable by reacting(A) a polyalkylene oxide obtained from ethylene oxide and propylene oxide and containing in total from 5 to 200 alkylene oxide units with(B) an alkylolation product of a low molecular weight aldehyde and a bis-(4-hydroxyphenyl)-methane of the general formula II ##STR1## wherein R.sup.1 and R.sup.2 may be identical or different and are each hydrogen, low molecular weight alkyl, phenyl, carboxyl or low molecular weight alkoxycarbonyl, the molar reaction ratio of the compound of the formula II to the alkylolating aldehyde being from 1:1 to 1:4, at from 100.degree. to 180.degree. C. in the presence of an acidic catalyst with removal of the water of reaction, the weight ratio of A to B being from 5:1 to 1:3.Type: GrantFiled: April 28, 1987Date of Patent: March 21, 1989Assignee: BASF AktiengesellschaftInventors: Klaus Barthold, Knut Oppenlaender, Juergen Lasowski, Richard Baur
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Patent number: 4814094Abstract: The method of recovering petroleum from a subterranean reservoir preferably comprising the steps of: (1) introducing through an injection well a predetermined amount of a polyalkylene oxide adduct of a fusible, aromatic hydrocarbon soluble synthetic resin which contains between about 4 to about 16 phenolic groups and is a condensate of a substituted phenol and an aldehyde, said condensate resin being further condensed with ethylene oxide and at least one other alkylene oxide containing 3 or 4 carbon atoms and in such amounts that the weight ratio of condensed alkylene oxide moiety to phenolic resin moiety ranges from about 1-to-1 to about 100-to-1 and the weight percentage of ethylene oxide residues to the total of all alkylene oxide residues ranges from about 20% to about 75%; said adduct (a) being soluble in water to the extent of about 1% or more at 25.degree. C. and (b) said 1% solution having a cloud point of less than about 70.degree. C.Type: GrantFiled: September 18, 1987Date of Patent: March 21, 1989Assignee: Magna CorporationInventors: Charles M. Blair, Jr., Charles A. Stout, Raymond P. Olsen
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Patent number: 4810776Abstract: In a process for producing epoxy resin with low EHC-content there is added to a continuous flow of the chlorine-substituted starting material continuously, with all reaction parameters constant, a dehydrochlorinizing agent, e.g. NaOH, in an amount approximately the stoichiometrical equivalent of the predetermined EHC-content of the starting material. Ionically bound chlorine is removed from the epoxy resin. A stream of a bypassing portion of the epoxy resin is subjected continuously, with brief periodical interruptions, directly after removal of the ionically bound chlorine, to fluorescence-exciting X-ray irradiation and the total chlorine fluorescence is detected, thereby automatically continuously determining the total chlorine content.Type: GrantFiled: July 6, 1987Date of Patent: March 7, 1989Assignee: Ciba-Geigy CorporationInventors: Bernhard Karlhuber, Andre Fiaux, Thierry Schaffhauser
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Patent number: 4789711Abstract: The invention relates to compounds of the formula I ##STR1## in which A is a group ##STR2## R.sup.1 is hydrogen or methyl R.sup.2 is C.sub.1 -C.sub.6 -alkyl, halogen or phenyl,X is a direct C--C bond, --CH.sub.2 -- or --SO.sub.2 --,m is 0, 1, 2 or 3, n is 0, 1 or 2 andp is 0 or, in the case of X=--CH.sub.2 --, can also be an integer from 1 to 6, with the proviso that the groups --A and --O--A are in the ortho-position relative to one another.The compounds can preferably be used as matrix resins for composite materials.The invention also relates to the allyl glycidyl ether intermediates, from which the compounds of the formula I are as a rule prepared by epoxidation with peracids.Type: GrantFiled: November 23, 1987Date of Patent: December 6, 1988Assignee: Ciba-Geigy CorporationInventors: Charles E. Monnier, Sameer H. Eldin, Peter Flury
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Patent number: 4785061Abstract: The total halide content of epoxy resins is reduced by heating a resin containing undesirable halide dissolved in a solvent mixture containing at least one polar aprotic solvent in the presence of an alkali metal hydroxide for a time sufficient to reduce the total halide content.Type: GrantFiled: August 13, 1987Date of Patent: November 15, 1988Assignee: The Dow Chemical CompanyInventors: Chun S. Wang, Zeng-Kun Liao
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Patent number: 4783363Abstract: An improvement in curable compositions which comprise a polyglycidyl ether such as the triglycidylether of tris(hydroxyphenyl)methane and a halogenated dihydric phenol such as tetrabromobisphenol A, the improvement being employing as the halogenated dihydric phenol one in which the halogen atoms are meta with respect to the hydroxyl groups such as 2,2',6,6'-tetrabromo-3 ,3',5,5'-tetramethyl-4,4'-biphenol. These compositions can be cured by heating in the presence or absence of a catalyst for reacting epoxy groups with phenolic hydroxyl groups such as 2-methyl imidazole. These compositions are particularly useful in the preparation of electrical laminates.Type: GrantFiled: March 11, 1987Date of Patent: November 8, 1988Assignee: The Dow Chemical CompanyInventors: Jody R. Berman, Abel Mendoza
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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: 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: 4755543Abstract: Phenol-aldehyde novolac resins having reduced quantities of 2-functional material are prepared by removing all or part of the 2-functional material from this product resulting from reacting phenol with an aldehyde. Epoxy novolac resins prepared from the novolac resin containing less 2-functional product exhibit increased Tg values when cured.Type: GrantFiled: February 18, 1987Date of Patent: July 5, 1988Assignee: The Dow Chemical CompanyInventors: James L. Bertram, Louis L. Walker, Avis L. McCrary, Fermin M. Cortez
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Patent number: 4755568Abstract: The 2-functional component of substituted phenol-aldehyde novolac resins is reduced. Epoxy novolac resins prepared from the novolac resin containing reduced quantities of 2-functional product exhibit increased Tg values when cured.Type: GrantFiled: February 18, 1987Date of Patent: July 5, 1988Assignee: The Dow Chemical CompanyInventors: James L. Bertram, Louis L. Walker, Avis L. McCruary, Fermin M. Cortez
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Patent number: 4755569Abstract: A thermosetting resin composition comprising (A) a phenol novolac resin, some of the hydroxyl groups of which have been allyl-etherified and the other hydroxyl groups having added thereto a compound having one or more epoxy groups and (B) a polymaleimide compound having two or more maleimide groups in the molecule.Type: GrantFiled: March 2, 1987Date of Patent: July 5, 1988Assignee: Sumitomo Chemical Company, LimitedInventors: Shuichi Kanagawa, Shigeo Hozumi, Kunimasa Kamio
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Patent number: 4755580Abstract: A coated article is made by: (1) admixing an epoxy resin, with a dual curing agent admixture of (a) an irradiated mixture of carboxylic acid anhydride and carbon containing cyclic compound and (b) a boron trihalide complex selected from at least one of boron trihalide:amine and boron trihalide:ether, (2) applying the mixed resin and concentrated dual curing agent to the surface of an article, and (3) curing the applied resin and curing agent.Type: GrantFiled: November 3, 1986Date of Patent: July 5, 1988Assignee: Westinghouse Electric Corp.Inventors: Howard E. Saunders, Rajender K. Sadhir, Richard D. Buckley
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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: 4724253Abstract: Adducts are prepared from partially hydrolyzed epoxy resins having an average functionality of at least about 2.6 such as a partially hydrolyzed phenol-formaldehyde epoxy novolac resin and a polyamine such as diethylenetriamine. These adducts are useful in preparing low temperature curable epoxy resin compositions.Type: GrantFiled: June 13, 1986Date of Patent: February 9, 1988Assignee: The Dow Chemical CompanyInventors: Michael B. Cavitt, Shari E. McMillan
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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: 4722981Abstract: Epoxy resins containing both terminal hydroxyl groups and epoxy or epoxy-derived groups are prepared by advancing a polyepoxide with a polyol and terminating the reaction at a point such that the epoxy resin reaction product contains both epoxy and terminal hydroxyl groups. The controlled conversion resins have improved cure rates. The epoxy groups can be further reacted to form epoxy-derived groups to improve the cure rate even further. The epoxy resins exhibit lower melt and solution viscosities than those exhibited by conventional epoxy resins having the same epoxy equivalent weight, as well as curing quickly when used. The resins are usefully employed at high solids levels in can coating formulations and other epoxy formulations wherein the resin is applied from an organic liquid solution or aqueous dispersion.Type: GrantFiled: January 29, 1987Date of Patent: February 2, 1988Assignee: The Dow Chemical CompanyInventors: Raymond A. Koenig, Brian W. Elliott
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Patent number: 4714648Abstract: A prepreg obtained by impregnating fibers with an epoxy resin composition by a hot melt method is described, wherein the epoxy resin composition comprises components (A), (B), and (C), wherein(A) is an epoxy resin(B) is a hardening agent composition containing a hydrazide type hardening agent for an epoxy resin, and having a melting point of not higher than 160.degree. C., and (B) further contains at least one compound selected from the group consisting of alcohols and phenols having a melting point of not less than 50.degree. C.,(C) is a urea compound represented by the formula ##STR1## wherein X and Y each represents H, Cl, or OCH.sub.3.Type: GrantFiled: August 1, 1985Date of Patent: December 22, 1987Assignee: Toho Rayon Co., Ltd.Inventor: Yasuhisa Nagata
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Patent number: 4711935Abstract: A process for producing self-crosslinking cationic paint binders, water-dilutable upon protonation, on the basis of urea and urethane group carrying reaction products of modified phenols and monoepoxy compounds as well as with the binders produced according to this process and their use in stoving paints, particularly electrodeposition paints are described. The process is characterized in that a substituted urea-phenol-formaldehyde condensate obtained through reaction of an aminoalkylation product of a phenol, carrying an average of at least one secondary amino group with a semi-blocked diisocyanate, or a substituted urea prepared from a semi-blocked diisocyanate and an amine and further reacted with formaldehyde and a phenol, is reacted with a monoepoxy compound, the free aliphatic hydroxy groups of the reaction product being reacted in a further reaction step with di- or polyisocyanates. The paints formulated with these products, at stoving temperatures of from 150.degree. to 170.degree. C.Type: GrantFiled: July 22, 1986Date of Patent: December 8, 1987Assignee: Vianova Kunstharz, A.G.Inventors: Johann Gmoser, Willibald Paar, Michael Honel