Nitrogen Reactant Having At Least One Amino-nitrogen Atom Contains A Cycloaliphatic Ring Patents (Class 528/122)
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Patent number: 5656862Abstract: Solder interconnection encapsulant, encapsulated structure and method for its fabrication and use, whereby the gap created by solder connections between a carrier substrate and a semiconductor device is filled with a composition obtained from curing a preparation containing a cycloaliphatic polyepoxide and/or curable cyanate ester or prepolymer thereof; filler, e.g., an aluminum nitride or aluminum oxide filler, having a maximum particle size of 31 microns.Type: GrantFiled: May 6, 1993Date of Patent: August 12, 1997Assignee: International Business Machines CorporationInventors: Kostas I. Papathomas, David Wei Wang
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Patent number: 5631332Abstract: A curing agent for epoxy resins, prepared by reacting 2,5- and 2,6-bis(aminomethyl)-bicyclo[2.2.1]heptanes (1 equivalent of the active hydrogen in the amino group) with an epoxy resin (a reaction product of bisphenols or a novolak resin with epichlorohydrin; an epoxy equivalent of 150-300 g/eq.; two or more epoxy groups per molecule; bisphenol-A diglycidyl ether or bisphenol-F diglycidyl ether in particular)(0.025-0.50 equivalents of the epoxy group). The reaction temperature is 40.degree.-120.degree. C. The amount of the curing agent is within the range of 20-75 parts by weight relative to 100 parts by weight of an epoxy resin to be cured. The curing agent has a high curing rate at a room temperature, and the epoxy resins cured by it have a good appearance as well as excellent adhesion, water resistance, and chemical resistance. Therefore, the curing agent is suitable for paints, civil engineering and construction materials, adhesives, casting resins, laminates, etc.Type: GrantFiled: January 11, 1996Date of Patent: May 20, 1997Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Minato Karasawa, Takuji Shimizu
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Patent number: 5591812Abstract: A curable epoxy resin composition comprising a polyepoxide resin and an amine curative characterized in that the amine curative comprises (a) the reaction product of excess monomethylamine (MMA) and an aliphatic or cycloaliphatic polyglycidyl ether and (b) an amine curative. When a diglycidyl ether is used in the reaction the resulting product can be described by the following structure: ##STR1## where R is an aliphatic, cycloaliphatic or aromatic organic radical and m is 0-3.Type: GrantFiled: January 26, 1996Date of Patent: January 7, 1997Assignee: Air Products and Chemicals, Inc.Inventor: William E. Starner
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Patent number: 5563224Abstract: Novel aminoplast anchored UV stabilizers are provided. Compared to unanchored stabilizers, the anchored stabilizers disclosed herein have increased compatibility with coating resins and have reduced volatility due to higher molecular weights resulting from anchoring. A process for preparing the anchored stabilizers by the reaction of unanchored stabilizers with alkoxymethylated aminoplasts in a sulfuric acid medium is also provided. The unanchored stabilizers include 2-(2-hydroxyaryl)benzotriazoles, 2-hydroxybenzophenones, 2-(2-hydroxyaryl)-4,6-diaryl-1,3,5-triazines, salicylic acid derivatives, 2-hydroxyoxanilides, and blocked derivatives thereof as well as mixtures of two or more stabilizers. The aminoplasts include alkoxymethylated derivatives of glycolurils, melamines, and benzoguanamines.Type: GrantFiled: May 23, 1995Date of Patent: October 8, 1996Assignee: Cytec Technology Corp.Inventors: Jeno G. Szita, Paul S. Waterman
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Patent number: 5559086Abstract: In one embodiment, an epoxy resin composition is provided comprising: an epoxy resin and a partially reduced aromatic amine hardening agent. In another embodiment, a well treating composition is provided comprising: an epoxy resin; a partially reduced aromatic amine hardening agent; a solid particulate material; and a carrier fluid. In yet another embodiment, a method of treating a subterranean formation is provided. The inventive method comprises the step of placing the inventive well treating composition into the formation.Type: GrantFiled: December 13, 1993Date of Patent: September 24, 1996Assignee: Halliburton CompanyInventors: Brahmadeo Dewprashad, Jimmie D. Weaver
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Patent number: 5508373Abstract: A method of curing an epoxy resin comprising mixing an epoxy resin with a curing agent is provided. The curing agent is selected from the group consisting of (i) a mixture consisting essentially of 1,2-diaminocyclohexane and an aliphatic polyamine (preferably at a molar ratio of 1,2-diaminocyclohexane to aliphatic polyamine of from about 1:1 to about 16:1, preferably about 2.5:1 to about 6:1 and more preferably about 3:1 to about 5:1) and (ii) the reaction product of reactants consisting essentially of an amine component consisting essentially of 1,2-diaminocyclohexane and an aliphatic polyamine and an epoxide component. The epoxide component has an epoxy functionality greater than one and is preferably a diglycidyl ether of an aromatic diol having an average degree of oligomerization of less than about 3.5., preferably less than about 1.5, and preferably derived from an alkyl bis-phenol, e.g. bisphenol A.Type: GrantFiled: August 4, 1994Date of Patent: April 16, 1996Assignee: Henkel CorporationInventors: Shailesh Shah, Robert M. Moon
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Patent number: 5459204Abstract: The invention relates to a new polyamine of the following composition: ##STR1## wherein 1.gtoreq.n.gtoreq.6, R represents the hydrocarbon radical of a (cyclo)aliphatic, araliphatic or aromatic diisocyanate having 6-20 C atoms or a trimer thereof andwherein when 2.gtoreq.n.gtoreq.6,R.sup.1 represents an n-valent organic radical such as is formed by removal of n OH groups from a polyhydroxy compound which optionally contains ether oxygen atoms and has an average molecular weight Mn of between 60 and 5,000; andwhen n=1,R.sup.1 represents ##STR2## It furthermore relates to a process for the preparation of a polyamine, in which certain diisocyanates, adducts of diisocyanates with polyols or trimers thereof are reacted with the Schiff base of the following composition: ##STR3## wherein R.sup.2 =H or a branched or unbranched C.sub.1-14 -alkyl radical and R.sup.3 =a branched or unbranched C.sub.1-14 -alkyl radical, an C.sub.1-14 alkyl-substituted phenyl radical or a C.sub.1 -C.sub.Type: GrantFiled: March 7, 1994Date of Patent: October 17, 1995Assignee: Huels AktiengesellschaftInventors: Rainer Lomoelder, Wilfried Paulen, Felix Schmitt, Elmar Wolf
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Patent number: 5414067Abstract: This invention relates to an improved method for curing polyepoxide resins at elevated temperature and particularly to a method for reducing the time required to effect cure of thermosetting resins at elevated temperature without sacrificing performance. In the basic process, an epoxide resin comprising a polyglycidyl ether of a polyhydric phenol is mixed with cycloaliphatic amine, e.g., di(4-aminocyclohexyl)methane, di(4-amino-3-methylcyclohexyl)methane, and isophoronediamine in an amount sufficient to effect cure of the polyepoxide resin at an initial temperature and then raised to a final cure temperature. The improvement for reducing the time necessary for cure comprises:effecting an initial and partial cure of the epoxy resin at a temperature between 60.degree. and 100.degree. C.Type: GrantFiled: May 25, 1994Date of Patent: May 9, 1995Assignee: Air Products and Chemicals, Inc.Inventors: Menas S. Vratsanos, Andrea K. Smith
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Patent number: 5412044Abstract: Adducts containing terminating nitro (nitroso) groups and one or more mesogenic moieties are prepared by reacting (A) at least one compound containing an average of more than one vicinal epoxide group per molecule with (B) at least one compound containing one or more nitro (nitroso) groups and an average of one reactive hydrogen atom per molecule; with the proviso that at least one member of components (A) and (B) contains a mesogenic moiety. Reduction of these adducts provides amines which are useful as curing agents for epoxy resins.Type: GrantFiled: May 12, 1994Date of Patent: May 2, 1995Assignee: The Dow Chemical CompanyInventors: Robert E. Hefner, Jr., Jimmy D. Earls
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Patent number: 5374769Abstract: Novel polycyanate compositions containing one or more mesogenic moieties as lateral substituents are disclosed which provide improved processability relative to polycyanates containing one or more mesogenic moieties in the main chain of the molecule. Molecular level ordering of the resulting thermosets is maintained much similar to that found thermosets of polycyanates which have one or more mesogenic moieties in the main chain.Type: GrantFiled: December 24, 1992Date of Patent: December 20, 1994Assignee: The Dow Chemical CompanyInventors: Robert E. Hefner, Jr., Jimmy D. Earls
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Patent number: 5373068Abstract: Use of isophoronediamine isomer mixtures containing more than 40%, preferably more than 50 up to 70%, of the trans-isomer and less than 60%, preferably less than 50 down to 30%, of the cis-isomer as reactant in polyaddition resins selected from epoxy, polyurethane and polyurea resins. As curing agents in epoxy resins compared with previously known isomer mixtures, the isomer mixtures containing more than 40% of the trans-isomer and less than 60% of the cis-isomer unexpectedly lead to an extended pot life with simultaneously reduced maximum curing temperature and therefore reduced shrinkage problems. The isomer mixtures are also surprisingly suitable as amine components with reduced reactivity for the chain extension of polyurethane/polyureas.Type: GrantFiled: September 9, 1993Date of Patent: December 13, 1994Assignee: Degussa AktiengesellschaftInventors: Hermann Piana, Klaus Huthmacher
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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: 5310770Abstract: Water-reducible curing agents for epoxy resins are made from the diglycidyl ether of cyclohexane dimethanol and a diamine selected from the group consisting of meta-xylylene diamine, isophorone diamine, diaminocyclohexane and 1,3-bisaminomethyl cyclohexane.Type: GrantFiled: December 30, 1992Date of Patent: May 10, 1994Assignee: Hi-Tek Polymers, Inc.Inventors: William J. DeGooyer, George A. Roy, II
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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: 5288424Abstract: This invention pertains to alkyl substituted bi(cyclohexylamine) and derivatives having a high trans, trans-isomer distribution. This isomer distribution represents a thermodynamic mixture of the isomers and provides for extended pot life and extended thermal properties in epoxy resins which are not seen with the kinetic isomer mixture. The bridged cyclohexylamine and derivatives are represented by the formula: ##STR1## wherein; R.sup.1 is hydrogen or C.sub.1-4 alkyl;R.sup.2 is C.sub.1-4 alkyl; andR.sup.3 is hydrogen or C.sub.1-4 alkylThe invention also relates to epoxy resins cured with the bridged bi(cyclohexylamines).Type: GrantFiled: July 15, 1993Date of Patent: February 22, 1994Assignee: Air Products and Chemicals, Inc.Inventors: Peter A. Lucas, Gamini A. Vedage, Jeremiah P. Casey
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Patent number: 5280091Abstract: This invention pertains to epoxy resins having increased chemical resistance to solvents, and good cured mechanical properties which are prepared by curing the epoxy resins with a curing agent comprising a mixture of methylene bridged poly(cyclohexyl-aromatic)amines. The methylene bridged poly(cyclohexyl-aromatic)amine curing agents are the residue obtained from the distillation of a mixture of poly(cyclohexylaromatic)amines formed by the hydrogenation of crude methylenedianiline or crude di(4-amino-3-methylcyclohexyl)methane.Type: GrantFiled: February 7, 1992Date of Patent: January 18, 1994Assignee: Air Products and Chemicals, Inc.Inventors: David A. Dubowik, Peter A. Lucas, Andrea K. Smith
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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: 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: 5264501Abstract: This invention pertains to alkyl substituted bi(cyclohexylamine) and derivatives having a high trans,trans-isomer distribution. This isomer distribution represents a thermodynamic mixture of the isomers and provides for extended pot life and extended thermal properties in epoxy resins which are not seen with the kinetic isomer mixture. The bridged cyclohexylamine and derivatives are represented by the formula: ##STR1## wherein; R.sup.1 is hydrogen or C.sub.1-4 alkyl;R.sup.2 is C.sub.1-4 alkyl; andR.sup.3 is hydrogen or C.sub.1-4 alkylThe invention also relates to epoxy resins cured with the bridged bi(cyclohexylamines).Type: GrantFiled: August 9, 1991Date of Patent: November 23, 1993Assignee: Air Products and Chemicals, Inc.Inventors: Peter A. Lucas, Gamini A. Vedage, Jeremiah P. Casey
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Patent number: 5248757Abstract: Compounds containing at least one cyanate group, at least one maleimide group and at least one rodlike mesogenic moiety are prepared by reacting one or more aminophenols containing one or more rodlike mesogenic moieties with a stoichiometric quantity of a maleic anhydride per amine group of said aminophenol and then cyanating the resulting phenolic functional maleimide.Type: GrantFiled: July 7, 1992Date of Patent: September 28, 1993Assignee: The Dow Chemical CompanyInventors: Robert E. Hefner, Jr., Jimmy D. Earls
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Patent number: 5248758Abstract: Compounds containing at least one cyanate group, at least one maleimide group and at least one rodlike mesogenic moiety are prepared by reacting one or more aminophenols containing one or more rodlike mesogenic moieties with a stoichiometric quantity of a maleic anhydride per amine group of said aminophenol and then cyanating the resulting phenolic functional maleimide.Type: GrantFiled: July 7, 1992Date of Patent: September 28, 1993Assignee: The Dow Chemical CompanyInventors: Robert E. Hefner, Jr., Jimmy D. Earls
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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: 5219975Abstract: The present invention is directed to a process for the preparation of amines containing urethane and urea groups. The amines are produced by reacting A) isocyanate prepolymers containing urethane groups and in which the isocyanate groups are reversibly blocked with secondary monoamines with B) amines having molecular weights of from 60 to 500, which are at least difunctional and which have a total of at least two primary or secondary amino groups, with splitting off of the secondary monoamine. The invention is also directed to the amines so produced and to the use as a hardener for an epoxide resin.Type: GrantFiled: May 7, 1991Date of Patent: June 15, 1993Assignee: Bayer AktiengesellschaftInventors: Lutz Schmalstieg, Karl-Heinz Hentschel, Josef Pedain, Klaus Nachtkamp
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Patent number: 5066764Abstract: This invention relates to ditertiary-butyl substituted bridged di(cyclohexylamines) where the tert-butyl substituent is alpha to the amine group and to polyepoxide formulations incorporating the di(cyclohexylamine). The formula of the diamine is: ##STR1## wherein R is tert-butyl. The di(tertiary butyl)methylene bridged cyclohexylamines have delayed reactivity when incorporated in epoxy resins and they also enhance physical properties in high resilience polyurethane foams.Type: GrantFiled: June 26, 1990Date of Patent: November 19, 1991Assignee: Air Products and Chemicals, Inc.Inventors: Jeremiah P. Casey, Peter A. Lucas, Menas S. Vratsanos
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Patent number: 5057557Abstract: Epoxy resins are modified by reaction with an acidified polytertiary amine-containing compound. These modified epoxy resins when cured result in products having improved properties.Type: GrantFiled: May 11, 1990Date of Patent: October 15, 1991Assignee: The Dow Chemical CompanyInventors: Duane S. Treybig, Pong S. Sheih, John M. McIntyre
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Patent number: 5025067Abstract: An epoxy resin comprising an active hydrogen compound having at least three active hydrogen atoms capable of reacting with an epoxy group in its molecule or butadine or isoprene as a main monomer is modified with an oligomer having on average at least 1.5 equivalents of active hydrogen capable of reacting with an epoxy group in its molecule. An epoxy resin modified with a bisphenol and a compound having active hydrogen or acid anhydride groups capable of reacting with an epoxy group is also provided. A toner containing the epoxy resin as a binder is useful in electrostatography.Type: GrantFiled: November 16, 1988Date of Patent: June 18, 1991Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Yohzoh Yamamoto, Goro Suzuki, Hideo Nakamura, Kiyomi Yasuda
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Patent number: 5025078Abstract: This invention relates to polyepoxide resins cured with an amine composition containing 1-methyl-2,6-cyclohexanediamine. The resulting polyepoxide resins generally are more easily processable and have improved thermal stability, greater elongation and enhanced fracture toughness.Type: GrantFiled: February 2, 1990Date of Patent: June 18, 1991Assignee: Air Products and Chemicals, Inc.Inventors: Peter A. Lucas, Jeremiah P. Casey
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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: 4996279Abstract: Dissymmetric new epoxy polymer materials have improved processability because they can be cured at lower temperatures.Type: GrantFiled: October 7, 1988Date of Patent: February 26, 1991Assignee: Shell Oil CompanyInventor: Kenneth C. Dewhirst
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Patent number: 4946925Abstract: This invention relates to bridged cyclohexylamines represented by the formula: ##STR1## A is C.sub.0, --CH.sub.2 --, ##STR2## R.sub.1 is C.sub.1-3 alkyl R.sub.2 is C.sub.1-6 alkylR.sub.3 is C.sub.1 or C.sub.2 alkylR.sub.4 is H or C.sub.1-4 alkylx is 0 or 1y is 0 or 1These bridged bis(cyclohexylamine) derivatives are well suited as curing agents for epoxy resins. These compositions lead to enhanced processing of the epoxy resin and permit adjustment of the reactivity/performance in formulating epoxies which demonstrate superior high temperature properties.Type: GrantFiled: December 1, 1989Date of Patent: August 7, 1990Assignee: Air Products and Chemicals, Inc.Inventors: Herbert F. Strohmayer, Jeremiah P. Casey, Peter A. Lucas
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Patent number: 4861810Abstract: The present invention relates to a new thermoplastic polymer composition having the processing characteristics of a thermosetting polymer along with an improved balance of properties including improved modulus/glass transition temperature/toughness balance. These new polymer compositions are prepared by reacting certain amine compounds with certain diepoxide compounds to form linear units which are lightly crosslinked. Also disclosed and claimed are processes for preparing such compositions, cured compositions and end-use applications.Type: GrantFiled: August 15, 1988Date of Patent: August 29, 1989Assignee: Shell Oil CompanyInventor: Kenneth C. Dewhirst
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Patent number: 4780524Abstract: The invention relates to a water-dilutable binder for cationic electrocoating finishes. For the preparation of the binders(A) a di-epoxide compound with an epoxide equivalent weight below 2,000 is reacted with(B) a phenol- or thiol-containing compound which reacts monofunctionally with epoxide groups, and with(C) primary and/or secondary amines or their salts and/or the salt of a tertiary amine, a sulfide/acid mixture or phosphine/acid mixture or a mixture of these compounds, as well as, if desired, with(D) a polyfunctional alcohol, a polycarboxylic acid, a polysulfide or a polyphenol.The components A and B are used in a molar ratio of from 10:1 to 1:1, preferably from 4:1 to 1.5:1 and the reaction of the component A with the component B is carried out at 100.degree. to 190.degree. C., if desired in the presence of a catalyst.Type: GrantFiled: January 23, 1987Date of Patent: October 25, 1988Assignee: BASF Lacke + Farben AGInventors: Arnold Dobbelstein, Michael Geist, Gunther Ott, Georg Schon
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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: 4772680Abstract: The invention provides a liquid coating composition curable at ambient temperature comprising an acetoacetate groups-containing addition polymer having a number average molecular weight of 1000-100,000, a glass transition temperature of 250.degree.-370.degree. K., a hydroxyl number of 0-200 and a content of acetoacetate groups of 3,5-45% by weight, the acetoacetate groups being present as ester of hydroxyalkyl acrylate, hydroxyalkyl methacrylate or allyl alcohol structural units, and a polyamine having primary and/or secondary amino groups and blocked with an aldehyde or ketone. A process for coating a substrate with such composition is also provided.Type: GrantFiled: March 26, 1986Date of Patent: September 20, 1988Assignee: Akzo N.V.Inventors: Arie Noomen, Paul M. Vandevoorde, Jaap M. Akkerman
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Patent number: 4764579Abstract: An adhesive mixture comprising a multiplicity of contiguous deposits of a curable but uncured fluid resin and a fluid curing agent for the resin, said deposits being separated by a thin flexible barrier film of cured resin resulting from the interaction between the resin and curing agent.Type: GrantFiled: July 7, 1987Date of Patent: August 16, 1988Assignee: The Oakland CorporationInventor: Richard B. Wallace
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Patent number: 4732961Abstract: A spherical particulate adhesive comprising particles of a partially amine cured epoxy resin as the main component and having an average particle size of 0.3 to 500 .mu.m, in which particles of the epoxy resin contain an at least partially compatible agent homogeneously in the interior thereof. This adhesive is a heat-curable adhesive and has a very high bonding force. After bonding, the adhesive is chemically stable and is especially preferably used for bonding in the field of electronic material, such as liquid crystal display devices, which are apt to be degraded by impurities and for which high-precision bonding is required.Type: GrantFiled: September 18, 1986Date of Patent: March 22, 1988Assignee: Toray Industries, Inc.Inventor: Koichiro Oka
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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: 4721770Abstract: N-Cyanocarboxylic acid amide derivatives which contain two or three ##STR1## groupings in the molecule are useful as hardeners for epoxide resins.Type: GrantFiled: June 24, 1986Date of Patent: January 26, 1988Assignee: Ciba-Geigy CorporationInventors: Friedrich Stockinger, Friedrich Lohse, Roland Moser
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Patent number: 4699937Abstract: A synthetic resin carrying basic nitrogen groups, its preparation, coating materials prepared from this resin, and a process for cathodic electrocoating.This synthetic resin is obtained by reacting(A) an epoxy resin which(B) a diketimine of a diprimary amineand, if required,(C) with a secondary amine, which may additionally contain a tertiary amino group, with a ketimine of a primary monoamine and/or with a ketimine of a primary/tertiary diamine,a diketimine obtained from(B.sub.1) a ketone and(B.sub.2) a branched aliphatic diprimary diamine of 5 to 9 carbon atoms and/or(B.sub.3) one or more diaminodiamides which are obtained by condensation of 2 moles of diamine (B.sub.2) and 1 mole of a dicarboxylic acidbeing employed as component (B).After protonation with an acid, this synthetic resin is useful as a binder for cathodic electrocoating.Type: GrantFiled: December 12, 1985Date of Patent: October 13, 1987Assignee: BASF Farben+Fasern AktiengesellschaftInventors: Werner Loch, Eberhard Schupp, Rolf Osterloh, Klaas Ahlers
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Patent number: 4686272Abstract: An adhesive mixture comprising a multiplicity of contiguous deposits of a curable but uncured fluid resin and a fluid curing agent for the resin, said deposits being separated by a thin flexible barrier film of cured resin resulting from the interaction between the resin and curing agent.Type: GrantFiled: July 10, 1985Date of Patent: August 11, 1987Assignee: The Oakland CorporationInventor: Richard B. Wallace
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Patent number: 4612156Abstract: Resinous materials are produced in the substantial absence of a solvent by feeding to an extruder operated at a temperature sufficient to cause a reaction between the reactants (A) at least one material having an average of more than one vicinal epoxy group per molecule, (B) at least one material having an average of more than one group reactive with component (A) such as hydroxyl, thiol, carboxyl, isocyanate, thioisocyanate or secondary amine groups or a combination of such groups per molecule or a material having only one primary amine group per molecule, (C) at least one catalyst for promoting a reaction between components (A) and (B) if a catalyst is required to effect the reaction between components (A) and (B), and (D) optionally one or more chain terminators and thereafter recovering a resinous material resulting from the reaction between components (A) and (B) from said extruder.This process is useful in preparing advanced epoxy resins and phenoxy thermoplastic resins.Type: GrantFiled: November 19, 1985Date of Patent: September 16, 1986Assignee: The Dow Chemical CompanyInventors: Ben W. Heinemeyer, Sammy D. Tatum
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Patent number: 4594291Abstract: Relatively high molecular weight epoxy resins cured with conventional curing agents are disclosed wherein the relatively high molecular weight epoxy resin is prepared in the presence of the curing agents. The resultant cured epoxy resin has an improvement in Tg or toughness and the mixture prior to reaction and curing is much easier to apply as a coating or in the preparation of castings, laminates and the like as compared to applications of mixtures of relatively high molecular weight epoxy resins and the curing agents.Type: GrantFiled: March 25, 1985Date of Patent: June 10, 1986Assignee: The Dow Chemical CompanyInventors: James L. Bertram, Louis L. Walker, Jody R. Berman, James A. Clarke
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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: 4585850Abstract: This invention relates to reaction injection molded elastomers derived from high molecular weight amine terminated polyethers and/or high molecular weight polyols, a chain extender, a polyisocyanate, and flaked glass treated with an amino, chloro, and/or isocyanate silane coupling agent. The reaction injection molded (RIM) elastomers of this invention are useful, for example, as automobile body parts.Type: GrantFiled: August 30, 1984Date of Patent: April 29, 1986Assignee: Texaco Inc.Inventor: Richard J. G. Dominguez
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Patent number: 4582887Abstract: This invention relates to reaction injection molded elastomers derived from high molecular weight amine terminated polyethers and/or high molecular weight polyols, a chain extender, a polyisocyanate, a chloro and/or isocyanate silane coupling agent, and untreated filler material. The reaction injection molded (RIM) elastomers of this invention are useful, for example, as automobile body parts.Type: GrantFiled: August 30, 1984Date of Patent: April 15, 1986Assignee: Texaco Inc.Inventors: Richard J. G. Dominguez, David R. McCoy
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Patent number: 4525571Abstract: Curable synthetic resin mixtures, useful as surface coatings, are prepared by the reaction of solid or liquid epoxy resins with curing agents in turn prepared by the reaction of epichlorohydrin with a cycloaliphatic diprimary diamine in a molor ratio between 1:>1 to 1:2.Type: GrantFiled: June 27, 1984Date of Patent: June 25, 1985Assignee: Schering AGInventors: Christian Burba, Herbert Franz
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Patent number: 4461878Abstract: Disclosure is a novel hardening agent for epoxy resins which has quick cold hardening ability and high safety for human bodies. This hardening agent has the general formula: ##STR1## Epoxy resins hardened with this hardening agent have excellent mechanical properties at high temperatures.Type: GrantFiled: October 28, 1983Date of Patent: July 24, 1984Assignee: Takeda Chemical Industries, Ltd.Inventors: Ichiro Minato, Koichi Shibata, Itsuo Furuoya
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Patent number: 4435558Abstract: The method of hardening a glycidyl compound with a polyether urethane urea amino hardener is disclosed, said hardener being prepared by reacting (1) a blocked prepolymer prepared by reacting a phenolic compound with the reaction product of a polyether polyol with an excess of polyisocyanate, with (2) a polyfunctional amino compound.Type: GrantFiled: December 15, 1982Date of Patent: March 6, 1984Assignee: Schering AGInventors: Christian Burba, Hermann-Josef Lucas, Bernd Neffgen
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Patent number: 4426425Abstract: Disclosed are novel polyamine compounds having the general formula ##STR1## wherein R, R.sup.1, R.sup.2 and R.sup.3 are each independently selected from hydrogen and alkyl groups which may be substituted, the preparation of such compounds and their use as curing agents for epoxy resins.Type: GrantFiled: March 24, 1983Date of Patent: January 17, 1984Assignee: Eastman Kodak CompanyInventors: Raymond H. Good, Paul McBride