Material Contains A Boron Atom Patents (Class 528/91)
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Patent number: 5314720Abstract: In summary, the invention is related to the discovery of a class of compounds which inhibits the reaction of a polyepoxide with a curing agent at low temperatures. More particularly the invention relates to an epoxy resin composition comprisinga) a polyepoxide; andb) a cure inhibitor comprising boric acid.Type: GrantFiled: March 6, 1992Date of Patent: May 24, 1994Assignee: The Dow Chemical CompanyInventors: Joseph Gan, James L. Bertram
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Patent number: 5308895Abstract: In summary, the invention is related to the discovery of a class of compounds which inhibits the reaction of a polyepoxide with a curing agent at low temperatures. More particularly the invention relates to an epoxy resin composition comprisinga) a polyepoxide; andb) a cure inhibitor comprising boric acid or maleic acid.In another embodiment, the invention comprises an epoxy resin composition comprisinga) a polyepoxide;b) a cure inhibitor comprising boric acid or maleic acid,c) a curing agent without phenolic hydroxyl moieties, andd) optionally a catalyst for the reaction of the polyepoxide with the curing agent.In still another embodiment the invention relates to a composition useful for curing a polyepoxide which comprisesa) a curing agent capable of reacting with a polyepoxide at elevated temperatures; andb) an inhibiting amount of boric acid or maleic acid; and optionallyc) a catalytic amount of a catalyst useful for accelerating the reaction of a polyepoxide with the curing agent.Type: GrantFiled: March 6, 1992Date of Patent: May 3, 1994Assignee: The Dow Chemical CompanyInventors: Joseph Gan, James L. Bertram
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Patent number: 5302672Abstract: A 1,1-bis(2,7-diglycidyloxy-1-naphthyl)alkane as an epoxy resin; a 1,1-bis(2,7-dihydroxy-1-naphthyl)alkane as an intermediate for said epoxy resin; a process for producing said intermediate comprising reacting 2,7-dihydroxy-1-naphthalene and an aldehyde; a process for producing said epoxy resin comprising reacting said intermediate and an epihalohydrin; and an epoxy resin composition comprising said epoxy resin and a curing agent. The epoxy resin has a low melt viscosity while exhibiting excellent heat resistance.Type: GrantFiled: February 26, 1992Date of Patent: April 12, 1994Assignee: Dainippon Ink and Chemicals, Inc.Inventors: Ichiro Ogura, Shunji Ehara, Taku Kitamura, Hiroshi Sakata
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Patent number: 5300618Abstract: A curable resorcinol-based epoxy resin is disclosed having the general structural formula (I) ##STR1## wherein at least one of R.sub.1, R.sub.2, or R.sub.3 is selected from the group consisting of (a) the general structural formula (II) ##STR2## wherein R.sub.4 is selected from the group consisting of hydrogen and an alkyl group having 1 to about 4 carbon atoms, and (b) an allyl group.Type: GrantFiled: January 15, 1993Date of Patent: April 5, 1994Assignee: Indspec Chemical CorporationInventor: Raj B. Durairaj
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Patent number: 5294582Abstract: As a curing catalyst of epoxy resins, superacid salts of an N,N'-di- or N,N',N'-trisubstitued urea, the urea component of which is produced by reacting an organic isocyanate and a primary or secondary amine, at least one of which is monofunctional, are soluble in conventional organic solvents compatible with epoxy resins and catalyze the cationic polymerization reaction of epoxy resins at room temperature.Type: GrantFiled: June 14, 1993Date of Patent: March 15, 1994Assignee: Nippon Paint Co., Ltd.Inventors: Tadafumi Miyazono, Koji Tabuchi
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Patent number: 5278247Abstract: As a curing catalyst of epoxy resins, superacid salts of an N,N'-di- or N,N',N'-trisubstituted urea, the urea component of which is produced by reacting an organic isocyanate and a primary or secondary amine, at least one of which is monofunctional, are soluble in conventional organic solvents, compatible with epoxy resins and catalyze the cationic polymerization reaction of epoxy resins at room temperature.Type: GrantFiled: April 24, 1992Date of Patent: January 11, 1994Assignee: Nippon Paint Co., Ltd.Inventors: Tadafumi Miyazono, Koji Tabuchi
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Patent number: 5278260Abstract: A process for the preparation of epoxy resins having a specific reproducible content of .alpha.-glycol groups, which process comprises adding at least 0.0085 mol of glycidol or glycidol precursor compound per hydroxy-equivalent of a phenolic compound A which contains 2, 3 or 4 phenolic hydroxyl groups during the reaction of said phenolic compound A with an epihalohydrin which is unsubstituted or substituted in 2- or 3-position by C.sub.1 -C.sub.4 alkyl. The products may be used for surface protection.Type: GrantFiled: October 13, 1992Date of Patent: January 11, 1994Assignee: Ciba-Geigy CorporationInventors: Werner Schaffner, Dimiter Hadjistamov
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Patent number: 5169473Abstract: Products resulting from contacting (1) at least one compound selected from the group consisting of (a) at least one onium compound of the element nitrogen, phosphorus, sulfur or arsenic; (b) at least one amine compound; and (c) a mixture of any two or more of the (a) and (b) components; with (2) either (a) boric acid or (b) a mixture of boric acid and at least one acid having a weak nucleophilic anion are suitable catalysts for reacting vicinal epoxy-containing compounds with aromatic hydroxyl-containing compounds.Type: GrantFiled: May 21, 1990Date of Patent: December 8, 1992Assignee: The Dow Chemical CompanyInventors: James L. Bertram, Louis L. Walker, Charlie Z. Hotz
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Patent number: 5162438Abstract: In an adhesive for printed circuit boards, whose main components are an epoxy resin and a polymer rubber, the improvement wherein the polymer rubber is a hydrogenated conjugated diene polymer rubber having not more than 100 ppm of metal content, not more than 100 ppm of ion content as determined by ion chromatography, and an iodine value of not more than 120, the ratio by weight of the hydrogenated conjugated diene polymer rubber to the epoxy resin in the adhesive being 35-75 weight % to 65-25 weight %.Type: GrantFiled: August 27, 1991Date of Patent: November 10, 1992Assignee: Nippon Zeon Co., Ltd.Inventor: Suguru Tsuji
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Patent number: 5162439Abstract: In an adhesive for printed circuit boards, whose main components are an epoxy resin and a polymer rubber, the improvement wherein the polymer rubber is a hydrogenated conjugated diene polymer rubber having not more than 100 ppm of metal content, not more than 100 ppm of ion content as determined by ion chromatography, and an iodine value of not more than 120.Type: GrantFiled: November 17, 1989Date of Patent: November 10, 1992Assignee: Nippon Zeon Co., Ltd.Inventor: Suguru Tsuji
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Patent number: 5132374Abstract: Adducts of the formula I ##STR1## are described in which R.sup.1 is an e-valent aliphatic radical after the removal of the functional groups, X is --O--or --NH--, R.sup.2 is a d+l-valent carbocyclic-aromatic radical, R.sup.3 is hydrogen or methyl, R.sup.4 is an aliphatic, aromatic, or araliphatic c+l-valent radical, Y is --O--, --S--or --NR.sup.5 --, R.sup.5 is hydrogen or ##STR2## b is an integer from 2 to 15, b is an integer from 1 to 25, c is 1, 2 or 3, d is 1, 2 or 3 and e is 2, 3 or 4.The adducts can be combined with latent curing agents and, if appropriate, other epoxy resins to give adhesives having good stability on storage and high flexibility.Type: GrantFiled: March 28, 1991Date of Patent: July 21, 1992Assignee: Ciba-Geigy CorporationInventors: Franz-Josef Reischmann, Madan M. Bagga
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Patent number: 5075389Abstract: New .alpha.-phenyl-glycidyl-ether polyolefin macromonomers and copolymer of these macromonomers and ring opening polymerizable monomers have been prepared. The new copolymers based on these macromonomers form a unique set of copolymers having graft type blocks of a hydrophobic polyolefin dangling from a back bone composed of a ring opening polymerizable monomer.Type: GrantFiled: February 14, 1991Date of Patent: December 24, 1991Assignee: University of AkronInventors: Joseph P. Kennedy, John D. Carter
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Patent number: 5070161Abstract: Benzyl pyridinium or ammonium salts of a non-nucleophilic anion are useful as a cationic polymerization initiator having a heat latency. A variety of resinous compositions containing this initiator is also disclosed.Type: GrantFiled: May 25, 1989Date of Patent: December 3, 1991Assignee: Nippon Paint Co., Ltd.Inventors: Shinji Nakano, Hiroharu Ohsugi, Yasuhiko Nakae, Hisaki Tanabe, Ryozo Takagawa, Yoshio Eguchi, Koichi Tsutsui, Takeshi Endo
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Patent number: 5066735Abstract: Electrical laminates are prepared from prepreg materials prepared by impregnating a substrate with a laminating varnish comprising a solvent solution of a curable composition comprising (A) a mixture of at least one epoxy resin having an average of more than 1 but not more than 2 vicinal epoxy groups per molecule and at least one epoxy resin having an average of more than 2 vicinal epoxy groups per molecules; (B) a mixture of at least one phenolic hydroxyl-containing compound having an average of more than 1 but not more than 2 phenolic hydroxyl groups per molecule and at least one phenolic hydroxyl-containing compound having an average of more than 2 phenolic hydroxyl groups per molecule; and (C) at least one catalyst for effecting the reaction between (A) and (B).Type: GrantFiled: April 12, 1990Date of Patent: November 19, 1991Assignee: The Dow Chemical CompanyInventors: Louis L. Walker, Paul A. Larson
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Patent number: 5047376Abstract: The present invention relates to activated curing combinations for organic cationically polymerizable materials. The curing combinations are obtainable by activating a solution or a dispersion of an iron/arene salt and a polycarboxylic acid, an anhydride based on a polycarboxylic acid, or a polyisocyanate by heating or by irradiation with actinic radiation. The curable compositions containing these activated curing combinations can be used as sheathing or encapsulating materials for electronic components.Type: GrantFiled: July 27, 1989Date of Patent: September 10, 1991Assignee: Ciba-Geigy CorporationInventors: Dieter Baumann, Kurt Meier, Werner Margotte, Beat Muller
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Patent number: 5011721Abstract: Chemorheologically viscosity tailored matrix resin formulation for use in forming prepregs and filament wound composite articles and having a specified viscosity profile comprising a curable matrix resin and an effective amount of a reactive resin curing agent reactive at room temperature and a latent resin curing agent substantially non-reactive at room temperature but activated upon heating or radiation such that the matrix resin formulation is adapted upon formulation to have a viscosity sufficiently low enough to enable the matrix resin to impregnate a filament or fiber at room temperature without the necessity for the application of heat or solvent and which, upon standing at room temperature after impregnation into the fiber or filament to form a prepreg composition, rises in viscosity to a viscosity level sufficiently high to prevent substantially any bleed of the matrix resin from winding tension upon spooling of the prepreg yet of sufficiently low enough viscosity to allow the prepreg to tack and draType: GrantFiled: October 16, 1989Date of Patent: April 30, 1991Assignee: Thiokol CorporationInventors: Owen H. Decker, Neal A. Mumford
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Patent number: 5001212Abstract: The present invention provides an additive for heat-hardenable epoxide resin masses, wherein the additive contains or consists of adducts and/or reaction products of (a) imidazoles of the general formula: ##STR1## in which R.sub.1, R.sub.2, R.sub.3 and R.sub.4, which can be the same or different, are hydrogen atoms, alkyl, alkenyl or alkynyl radicals containing up to 3 carbon atoms or phenyl radicals, said radicals being unsubstituted or substituted, and (b) at least one aromatic hydroxy acid.The additives according to the present invention can be used alone as hardeners or, in combination with other latent hardeners, as accelerators.Type: GrantFiled: June 27, 1989Date of Patent: March 19, 1991Assignee: SKW Trostberg AktiengesellschaftInventors: Benedikt Hammer, Bernd Graml
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Patent number: 4959425Abstract: Electrical laminates are prepared from prepreg materials prepared by impregnating a substrate with a laminating varnish comprising a solvent solution of a curable composition comprising (A) a mixture of at least one epoxy resing having an average of more than 1 but not more than 2 vicinal epoxy groups per molecule and at least one epoxy resin having an average of more than 2 vicinal epoxy groups per molecule; (B) a mixture of at least one phenolic hydroxyl-containing compound having an average of more than 1 but not more than 2 phenolic hydroxyl groups per molecule and at least one phenolic hydroxyl-containing compound having an average of more than 2 phenolic hydroxyl groups per molecule; and (C) at least one catalyst for effecting the reaction between (A) and (B).Type: GrantFiled: June 27, 1989Date of Patent: September 25, 1990Assignee: The Dow Chemical CompanyInventors: Louis L. Walker, Paul A. Larson
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Patent number: 4933421Abstract: Rapid-setting epoxy resins comprise a polyepoxide, a metal tetrafluoroborate, and at least one boron ester selected from the group of triesters of boric acid and diesters of boronic acid.Type: GrantFiled: March 30, 1989Date of Patent: June 12, 1990Assignee: Shell Oil CompanyInventor: Glen T. Morehead
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Patent number: 4929650Abstract: A coating material for a tendon for prestressed concrete includes a curing composition, the curing time of which is so controlled that the composition is held in an uncured fluid state for a predetermined time after the concrete hardens. After the predetermined time passes, the composition cures. By coating a tendon for prestressed concrete with the coating material having such properties, an antirust effect of the tendon, an improved adhering force of the tendon to the concrete and a decreased cost of manufacturing prestressed concrete can be obtained.Type: GrantFiled: July 25, 1988Date of Patent: May 29, 1990Assignees: Mitsui Sekiyu Kagaku Kogyo Kabushiki Kaisha, Shinko Kosen Kogyo Kabushiki KaishaInventors: Makoto Kurauchi, Michio Hashimoto, Kiyoshi Hayasaki, Toshikazu Minami, Mutsuhiko Ohnishi, Yohei Suzuki
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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: 4874669Abstract: Electrical laminates are prepared from prepreg materials prepared by impregnating a substrate with a laminating varnish comprising a ketone solvent solution of a curable composition comprising (A) at least one aromatic based epoxy resin having an average number of epoxide groups per molecule of more than 2; (B) a mixture of (1) at least one phenolic hydroxyl-containing compound having an average of more than 1 but not more than 2 phenolic hydroxyl groups per molecule; and (2) at least one phenolic hydroxyl-containing compound having an average of more than 2 phenolic hydroxyl groups per molecule; and (C), optionally, at least one catalyst for effecting the reaction between (A) and (B).Type: GrantFiled: August 15, 1988Date of Patent: October 17, 1989Assignee: The Dow Chemical CompanyInventors: Paul A. Larson, Dale J. Aldrich, Jody R. Berman
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Patent number: 4868059Abstract: Electrical laminates are prepared from prepreg materials prepared by impregnating a substrate with a laminating varnish comprising a solvent solution of a curable composition comprising (A) a mixture of at least one epoxy resin having an average of more than 1 but not more than 2 vicinal epoxy groups per molecule and at least one epoxy resin having an average of more than 2 vicinal epoxy groups per molecule; (B) a mixture of at least one phenolic hydroxyl-containing compound having an average of more than 1 but not more than 2 phenolic hydroxyl groups per molecule and at least one phenolic hydroxyl-containing compound having an average of more than 2 phenolic hydroxyl groups per molecule; and (C) at least one catalyst for effecting the reaction between (A) and (B).Type: GrantFiled: November 16, 1987Date of Patent: September 19, 1989Assignee: The Dow Chemical CompanyInventors: Louis L. Walker, Paul A. Larson
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Patent number: 4831099Abstract: A composition is provided comprising an epoxy resin, a cationic curing agent for the epoxy resin and a polyalkylene glycol present in the composition in an amount effective to increase the cure rate reproducibility of the curing agent.Type: GrantFiled: April 14, 1987Date of Patent: May 16, 1989Assignee: Shell Oil CompanyInventor: Larry S. Corley
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Patent number: 4775736Abstract: Epoxy resins having acceptable pot lives, degrees of reactivity, and physical properties are obtained by the use of curing agent compositions which comprise about 99.6-90% by weight of a hindered aromatic diamine, such as diethyltoluenediamine, and about 0.4-10% by weight of an accelerator complex of boron trifluoride and a cycloaliphatic diamine, such as isophoronediamine.Type: GrantFiled: August 26, 1987Date of Patent: October 4, 1988Assignee: Ethyl CorporationInventor: Paul L. Wiggins
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Patent number: 4775734Abstract: A curable composition comprising a polyepoxide, an amine curing agent and a catalytic amount of a non-nucleophilic acid salt of an amine having the formula R(R')(R")NH.sup.+ X.sup.- wherein R, R' and R" independently represent an alkyl group having from 1 to 20 carbon atoms, an alkaryl group having from 7 to 20 carbon atoms or an oxyalkylene group having from 2 to 50 carbon atoms and wherein R' and R" independently also may represent hydrogen and R may also represent the formula [--Y--(R')(R")NH.sup.+ X.sup.- ].sub.n wherein R' and R" have the foregoing designations, Y represents an alkylene or alkylene ether group having from 2 to 50 carbon atoms and n represents an integer of from 1 to 5 is described.Type: GrantFiled: August 12, 1987Date of Patent: October 4, 1988Assignee: Ashland Oil, Inc.Inventor: Anil B. Goel
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Patent number: 4772325Abstract: This invention relates to a fluorine-containing dental composition. The composition is particularly adapted for use in the field of dentistry as a composite filling material, cavity liner, adhesive, orthodontic resin, pit and fissure sealant, and denture base material wherein the fluoride is released to prevent secondary caries and reduce plaque formation.Type: GrantFiled: April 30, 1987Date of Patent: September 20, 1988Assignee: Kerr Manufacturing CompanyInventors: Stephen C. Kwan, John J. O'Connell
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Patent number: 4766196Abstract: A rapid curing epoxy resin composition comprising a mixture of(A) A first component comprising a polyepoxide and(B) A second component comprising a mixture of the novel reaction product of(1) an ammonium salt of a non-nucleophilic acid with(2) the reaction product of(a) a bicyclic amide acetal with(b) an amine, and(3) an amine curing agent, is described.Type: GrantFiled: August 14, 1987Date of Patent: August 23, 1988Assignee: Ashland Oil, Inc.Inventors: Anil B. Goel, Teresa A. DeLong
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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: 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: 4725652Abstract: Latent catalysts for epoxy reactions are prepared by reacting a tetrasubstituted onium compound such as tetrabutylphosphonium acetate.acetic acid complex or an amine compound with an acid having a weak-nucleophilic anion such as fluoboric acid. These catalysts provide stable latent catalysts for epoxy resins for advancement or curing reactions.Type: GrantFiled: March 4, 1987Date of Patent: February 16, 1988Assignee: The Dow Chemical CompanyInventors: James L. Bertram, Louis L. Walker, Van I. W. Stuart
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Patent number: 4724031Abstract: 2,6-Disubstituted 4-epoxypropyl glycidyl ethers of the formula ##STR1## wherein X is a group R' or X is a group of the formula ##STR2## and each of R and R' independently of the other is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, a halogen atom or C.sub.6 -C.sub.10 aryl, can be used, together with customary epoxy resin hardeners, for the preparation of cured products, in particular for application in the electronics industry, or as adhesives. Compounds of the formula are also valuable reactive diluents for curable epoxy resin mixtures.Type: GrantFiled: June 4, 1986Date of Patent: February 9, 1988Assignee: Ciba-Geigy CorporationInventors: Charles E. Monnier, Sheik Abdul-Cader Zahir, Sameer H. Eldin
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Patent number: 4717440Abstract: A two-part composition curable by contact of respective parts with one another, comprising: a first part comprising a cationically polymerizable material and a first latent curing component; and a second part comprising a cationically polymerizable material and a second latent curing component which is reactive with the first component to form cations which are curingly effective for the resin. A preferred class of cation species comprises carbenium ions derived from reaction of organic halide compounds, as the first component, with silver salts of non-nucleophilic anions, e.g., 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, The respective parts of the two-part composition may be applied to matable surfaces which then are contacted to effect rapid bonding cure of the composition.Type: GrantFiled: January 22, 1986Date of Patent: January 5, 1988Assignee: Loctite CorporationInventors: Kieran F. Drain, David J. Dunn
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Patent number: 4716185Abstract: Curable mixtures, containing,(a) at least one bisphenol diglycidyl ether based on bisphenol A, hydrogenated bisphenol A or bisphenol F,(b) as a curing catalyst, a colorless or slightly yellow solution of a metal complex compound of the formula I]Me(H.sub.2 O).sub.x (Lm).sub.y ].sup.2+ (A.sup..crclbar.).sub.2 (I),in whichMe is a divalent metal from the group comprising Zn, Cd, Sn, Pb, Ca or Mg,Lm is a saturated cyclic ether having 5 to 7 ring atoms, a linear or cyclic saturated aliphatic ether compound or a mixture of the ether and the ether compound, the ether and the ether compound having a boiling point of at least 60.degree. C., andA is an anion of the formula BF.sub.4.sup..crclbar., PF.sub.6.sup..crclbar., AsF.sub.6.sup..crclbar. or SbF.sub.6 .sup..crclbar.Type: GrantFiled: January 16, 1987Date of Patent: December 29, 1987Assignee: Ciba-Geigy CorporationInventors: Claus W. Rabener, Hans-Peter Horner, Dieter Baumann
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Patent number: 4707518Abstract: Epoxy adhesive compositions which are suitable for use in bonding metal and SMC parts to other metal and SMC parts comprise, in admixture, an epoxy resin, the adduct of an epoxy resin and a reactive (meth)acrylonitrile/butadiene rubber and a mixture of Lewis acid complexes having different cure times. The adhesive can be cured at elevated temperatures in 5 minutes or less.Type: GrantFiled: October 16, 1986Date of Patent: November 17, 1987Inventor: Dilipkumar N. Shah
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Patent number: 4705838Abstract: The process for acceleration of the cure rate of an epoxy resin which comprises forming a mixture of an epoxy resin, a boron trifluoride-amine complex and an isocyanate compound and curing said mixture at a temperature in the range of from about ambient to about 130.degree. C. is described.Type: GrantFiled: July 7, 1986Date of Patent: November 10, 1987Assignee: Ashland Oil, Inc.Inventor: Anil B. Goel
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Patent number: 4701513Abstract: This invention relates to the use of compositions of the formula: ##STR1## wherein n is 2 to 4 and X is --O--, --S-- or ##STR2## wherein R.sub.1 is an aliphatic or aromatic moiety as a curing agent for epoxy resins to form a thermoset material which has a reduced shrinkage.Type: GrantFiled: December 15, 1986Date of Patent: October 20, 1987Assignee: W. R. Grace & Co.Inventor: Shiow C. Lin
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Patent number: 4683282Abstract: A process for curing epoxide resins by mixing an epoxide resin with a boron trifluoride-amine complex catalyst wherein the amine moiety of the catalyst is a poly(alkylene oxide) poly amine and heating the resulting mixture at a temperature in the range of from about 100.degree. C. to about 200.degree. C. is described.Type: GrantFiled: August 21, 1986Date of Patent: July 28, 1987Assignee: Ashland Oil, Inc.Inventor: Anil B. Goel
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Patent number: 4668758Abstract: An epoxy resin composition containing a cationic curing agent and a cure-retarding amount of a diarylamine. The diarylamine lengthens the pot life of the epoxy-curing agent composition.Type: GrantFiled: September 30, 1985Date of Patent: May 26, 1987Assignee: Shell Oil CompanyInventor: Larry S. Corley
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Patent number: 4663072Abstract: This invention relates to a stable acid anhydride paste mixture useful as a crosslinking agent for epoxy resins and a dual catalyst system therefor. In particular, the anhydride mixture comprises high melting point acid anhydride, a liquid acid anhydride, and a low melting point acid anhydride. The dual catalyst system comprises tertiary amine catalysts with boron trihalide amine complex catalysts.Type: GrantFiled: December 24, 1984Date of Patent: May 5, 1987Assignee: Ford Motor CompanyInventor: Mo-Fung Cheung
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Patent number: 4661562Abstract: A process for the rapid formation of thermoset polymers by polymerizing a mixture of a polyepoxide with a polycarboxylic acid containing an alkali or alkaline earth metal cationic complex catalyst is disclosed.Type: GrantFiled: November 4, 1985Date of Patent: April 28, 1987Assignee: Ashland Oil, Inc.Inventor: Anil B. Goel
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Patent number: 4628080Abstract: A composition is provided comprising an epoxy resin, a cationic curing agent for the epoxy resin and a surfactant. The surfactant improves the reproducibility of cure rates of the cationic curing agent, particularly when the cationic curing agent is used in the form of an aqueous solution.Type: GrantFiled: September 30, 1985Date of Patent: December 9, 1986Assignee: Shell Oil CompanyInventor: Larry S. Corley
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Patent number: 4614788Abstract: Disclosed are thermosettable compositions comprising (A) an epoxy resin such as the diglycidyl ether of bisphenol A; (B) boron trifluoride complexed with a primary, secondary or tertiary amine such as monoethanolamine and (C) at least one cyclic or acyclic phosphazene having at least one pendant ##STR1## group wherein Z is an alkyl or an aryl group such as hexa(n-propylamino)cyclotriphosphazene.When cured, these compositions have an increased glass transition temperature (Tg) value as compared to a similar composition without the phosphazene compound.These compositions are useful in potting compositions, wet lay-up and pre-impregnated laminate, adhesive, molding, coating, casting, encapsulation, filament winding and transfer molding applications.Type: GrantFiled: August 28, 1985Date of Patent: September 30, 1986Assignee: The Dow Chemical CompanyInventors: Marvin L. Dettloff, Dennis L. Steele, Ross C. Whiteside, Jr.
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Patent number: 4607069Abstract: A solvent-free curable composition has a long shelf life and consists ofA 100 parts by weight of an epoxy resin andB from 10 to 100 parts by weight of, as a curing agent for the epoxy resin, an aromatic diamine containing ##STR1## groups, with or without C from 0.01 to 5 parts by weight of an accelerator, the curing agent for the epoxy resin being finely dispersed in the latter and preferably having a particle size of less than 10 .mu.m. The preferred epoxy resin curing agent is 4,4'-diaminodiphenyl ketone. The curable composition is used in particular for the preparation of fiber-reinforced materials.Type: GrantFiled: July 3, 1985Date of Patent: August 19, 1986Assignee: BASF AktiengesellschaftInventors: Helmut Tesch, Manfred Heym, Walter Doerflinger, Herbert Stutz, Peter Neumann, Dietmar Nissen, Gerhard Schaefer
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Patent number: 4593052Abstract: Polymerizable compositions contain (A) a cationically polymerizable material, such as an epoxide resin, a phenoplast or a cyclic vinyl ether, (B) a hydroxy compound such as styreneallyl alcohol copolymer, and (c) an aromatic iodosyl salt of formula ##STR1## where R.sup.3 and R.sup.4, which may be the same or different, each represent a monovalent aromatic radical having from 4 to 25 carbon atoms, x denotes 1, 2 or 3, and Z.sup.x- denotes an x-valent anion of a protic acid.Suitable salts of formula II include diphenyliodosyl hexafluorophosphate and tetrafluoroborate. The compositions may be photopolymerized or they may be thermally polymerized in the presence, as catalyst for the iodosyl salt, of a salt or complex of a d-block transition metal, a stannous salt, an organic peroxide or an activated .alpha.-hydroxy compound.The compositions may be used as surface coatings and adhesives, and in the preparation of printing plates, printed circuits and reinforced composites.Type: GrantFiled: November 19, 1984Date of Patent: June 3, 1986Assignee: Ciba-Geigy CorporationInventor: Edward Irving
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Patent number: 4569956Abstract: The present invention provides a rapid, low-temperature curing epoxy resin adhesive composition comprising (1) a polyepoxide, (2) a catalytic amount of HBF.sub.4, (3) a finely divided filler, preferably an acidic filler, and, optionally, (4) a polyalkylene ether glycol.Type: GrantFiled: August 8, 1984Date of Patent: February 11, 1986Assignee: Shell Oil CompanyInventors: Walter V. Breitigam, Roy J. Jackson
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Patent number: 4565837Abstract: Compounds with a plurality of oxirane functional groups can be cured to a fixture in less than one minute with a catalyst composition of a trityl or tropylium salt of a non-nucleophillic anion and a suitable solvent. Typical catalyst salts include trityl tetrafluoroborate, trityl hexachloroantimonate and tropylium hexafluorophosphate. The catalyst composition may conveniently be extended with liquid polymeric vehicles and acidic fillers.Type: GrantFiled: November 7, 1984Date of Patent: January 21, 1986Assignee: Loctite CorporationInventors: Kieran F. Drain, David J. Dunn
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Patent number: 4560709Abstract: Cationically polymerizable compounds, for example epoxide compounds, can be polymerized photochemically using a catalyst combination consisting of an aromatic iodonium salt and a ketone of the formula I, II or III ##STR1## in which n is 1 or 2 and Ar, X, X', R.sup.1, R.sup.2 and R.sup.3 are as defined in claim 1. In this combination, the ketones act as a co-catalyst and drastically accelerate the photopolymerization, although they are not able to initiate a cationic photopolymerization on their own.Type: GrantFiled: August 26, 1983Date of Patent: December 24, 1985Assignee: Ciba Geigy CorporationInventors: Godwin Berner, Rudolf Kirchmayr
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Patent number: 4503161Abstract: Microcapsules with liquid fills containing Lewis acid catalysts, catalyst concentrates comprising slurries of the microcapsules in liquid media, and a method for preparing the microcapsules and concentrates. The catalyst concentrates of the present invention are storage stable both alone and when incorporated in a one-part epoxy formulation.Type: GrantFiled: March 23, 1984Date of Patent: March 5, 1985Assignee: Minnesota Mining and Manufacturing CompanyInventors: Gerald E. Korbel, Richard G. Newell
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Patent number: 4482679Abstract: Compositions that cure when heated comprise(A) an epoxide resin and(B) an effective amount of(i) a diaryliodosyl salt of formula ##STR1## where R.sup.1 and R.sup.2, which may be the same or different, each represents a monovalent aromatic radical of from 4 to 25 carbon atoms, such as a substituted or unsubstituted phenyl group,M represents a metal or metalloid atom, such as phosphorus or boron,X represents a halogen atom, particularly chlorine or fluorine, andn is 4, 5, or 6, and is greater by one than the valency of M or MX.sub.n.sup.- represents pentafluorohydroxoantimonate, and(ii) a catalyst for the diaryliodosyl salt which is a salt or complex of a d-block transition metal, a stannous salt, an organic peroxide, or an .alpha.-hydroxy compound.Typically, the epoxide resin (A) is a bisphenol A diglycidyl ether, the salt (i) is diphenyliodosyl tetrafluoroborate or hexafluorophosphate, and the catalyst (ii) is cupric acetylacetonate or benzpinacol.Type: GrantFiled: September 9, 1983Date of Patent: November 13, 1984Assignee: Ciba-Geigy CorporationInventor: Edward Irving