Nitrogen-containing Alcohol, Inorganic Alcoholate, Or Ether Patents (Class 528/111)
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Patent number: 5874490Abstract: There is disclosed a self-dispersing curable epoxy resin composition comprising the addition product of reactants comprising (a) 1.0 reactive equivalent of an epoxy resin, (b) from about 0.40 to 0.95 reactive equivalents of a polyhydric phenol, and (c) from about 0.005 to 0.5 reactive equivalents of an amine-epoxy adduct comprising the addition product of reactants comprising 1.0 reactive equivalent of a polyepoxide and from about 0.3 to 0.9 reactive equivalents of a polyoxyalkyleneamine with the structural formulaH.sub.2 N--CH(R.sub.2)CH.sub.2 --O--R.sub.1 --CH.sub.2 CH(R.sub.2)--NH.sub. 2wherein:R.sub.1 represents a polyoxyalkylene chain having the structural formula:(CH.sub.2 --CH.sub.2 --O).sub.a --(CH.sub.2 --CH(R.sub.3)--O).sub.bwherein:R.sub.3 is a monovalent organic radical selected from the group consisting of C.sub.1 to C.sub.4 aliphatic hydrocarbons,`a` designates a number of ethoxy groups (CH.sub.2 --CH.sub.2 --O),`b` designates a number of monosubstituted ethoxy groups (CH.sub.2 --CH(R.sub.Type: GrantFiled: October 30, 1996Date of Patent: February 23, 1999Assignee: Henkel CorporationInventors: Kartar S. Arora, John G. Papalos, Grannis S. Johnson
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Patent number: 5855961Abstract: This invention relates to coating compositions including one or more resins having amino-reactive groups; one or more polyamine curing agents; and one or more aminourethanes. The aminourethanes can be reaction products of (i) oligomeric or polymeric compounds which contain at least one, preferably two or more terminal 2-oxo-1,3-dioxolane groups (cyclic carbonate groups), and (ii) amines containing at least one primary, preferably two or more primary and, if desired, also secondary and tertiary amino groups. The ratios of equivalents of C1):C2) typically is from 1:1 to 1:10, preferably from 1:1.05 to 1:5 and particularly preferably from 1:1.1 to 1:2, and the end product preferably contains one or more free primary amino groups. The composition further may contain, if desired, pigments, fillers, one or more organic solvents, water and conventional additives.Type: GrantFiled: May 12, 1997Date of Patent: January 5, 1999Assignee: Vianova Resins GmbHInventors: Michael Hoenel, Armin Pfeil, Thomas Budnick, Heiner Schwan
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Patent number: 5834620Abstract: Described herein are polyesters and polyamides which contain repeat units derived from novel dicarboxylic acids comprising arylene groups having ortho ethers substituted thereon. Also disclosed are novel compounds from which these polymers can be made. The polymers are especially useful for molding resins and coatings.Type: GrantFiled: November 14, 1997Date of Patent: November 10, 1998Assignee: University of LiverpoolInventors: Geoffrey Charles Eastmond, Jerzy Paprotny
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Patent number: 5798398Abstract: It has been found that non-blushing coatings of high gloss, long pot life and fast cure time may be obtained by using an epoxy curing agent which comprises an epichlorohydrin-metaxylylenediamine reaction product selected from the group consisting of N,N'-bis(3-aminomethylbenzyl)-2-hydroxytrimethylenediamine, the higher oligomers of N,N'-bis(3-aminomethylbenzyl)-2-hydroxytrimethylenediamine and mixtures thereof and a melting point depressant such as a benzyl alcohol or water and an alcohol solvent and, optionally, a tertiary amine such as N,N'-bis(3-(dimethylamino)propyl)-urea.Type: GrantFiled: October 18, 1996Date of Patent: August 25, 1998Assignee: Henkel CorporationInventors: Shailesh Shah, Ronald J. Cash, Ronald LaFreeda, James Aloye, Joseph L. Mulvey
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Patent number: 5763506Abstract: A self-dispersing curable epoxy composition is prepared upon contacting (a) 1.0 reactive equivalents of an epoxy resin, (b) from about 0.01 to 1.0 reactive equivalents of a polyhydric phenol, and (c) between 0.005 and 0.025 reactive equivalents of an amine-epoxy adduct, wherein the amine-epoxy adduct is formed upon contacting 1.0 equivalents of an aliphatic polyepoxide and between 0.3 and 0.9 reactive equivalents of a polyoxyalkyleneamine. The self-dispersing curable epoxy resin forms an aqueous dispersion upon mixing with water. When cured, the dispersion is useful as a coating composition.Type: GrantFiled: September 26, 1996Date of Patent: June 9, 1998Assignee: Henkel CorporationInventors: John G. Papalos, Reuben H. Grinstein, Shailesh Shah, Joseph L. Mulvey, Brian G. Jewell
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Patent number: 5760108Abstract: Self-dispersing curable epoxy resin ester dispersions prepared by a process comprising reacting a self-dispersing curable epoxy resin based on a polyoxyalkyleneamine with a fatty acid selected from the group consisting of drying oil and semi-drying oil fatty acids, are provided. The self-dispersing curable epoxy resin is based on a polyoxyalkyleneamine. Thus, a polyoxyalkyleneamine was present as a chemical precursor of the epoxy resin or a starting material therefor. The self-dispersing curable epoxy resin ester of the invention is in the form of an aqueous dispersion. When dried, films of the self-dispersing curable epoxy resin ester dispersion are useful as a coating composition.Type: GrantFiled: October 22, 1996Date of Patent: June 2, 1998Assignee: Henkel CorporationInventors: Kartar S. Arora, Grannis S. Johnson, James Aloye
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Patent number: 5723565Abstract: An epoxy resin composition comprises the cured reaction product of an epoxy base resin and a curing agent mixture. The curing agent mixture comprises an amino curative and a polyoxyalkylene polycarbonate. Liquid epoxy base resins cured with polyoxyalkyleneamines in the presence of polyoxyalkylene polycarbonates were harder and displayed improved tensile modulus, flexural strength and flexural modulus.Type: GrantFiled: April 12, 1993Date of Patent: March 3, 1998Assignee: Huntsman Petrochemical CorporationInventors: Michael Cuscurida, Kathy Beth Sellstrom
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Patent number: 5707702Abstract: A cross-linked pipelining network polymer composition for the in situ rehabilitation of pipes is formed. The polymer composition comprises at least one liquid epoxy resin and an effective amount of a liquid curing agent blend comprising an aliphatic polyamine, an aliphatic imidazoline, and an aliphatic amidoamine. The polymer composition may further comprise a pigment, a diluent and/or a viscosity controlling agent.Type: GrantFiled: June 26, 1996Date of Patent: January 13, 1998Inventors: Robert F. Brady, Jr., James D. Adkins
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Patent number: 5681907Abstract: A curable epoxy resin composition comprising a polyepoxide resin and an amine curative characterized in that the amine curative comprises the reaction product of excess monomethylamine (MMA) and a polyglycidyl ether. 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 4, 1996Date of Patent: October 28, 1997Assignee: Air Products and Chemicals, Inc.Inventors: William Edward Starner, John Anthony Marsella, Lloyd Gerald Easterday
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Patent number: 5652323Abstract: A self-dispersing curable epoxy composition is prepared upon contacting (a) 1.0 reactive equivalents of an epoxy resin, (b) from about 0.01 to 1.0 reactive equivalents of a polyhydric phenol, and (c) between 0.005 and 0.025 reactive equivalents of an amine-epoxy adduct, wherein the amine-epoxy adduct is formed upon contacting 1.0 equivalents of an aliphatic polyepoxide and between 0.3 and 0.9 reactive equivalents of a polyoxyalkyleneamine. The self-dispersing curable epoxy resin forms an aqueous dispersion upon mixing with water. When cured, the dispersion is useful as a coating composition.Type: GrantFiled: June 6, 1995Date of Patent: July 29, 1997Assignee: Henkel CorporationInventors: John G. Papalos, Reuben H. Grinstein, Shailesh Shah, Joseph L. Mulvey, Brian G. Jewell
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Patent number: 5652318Abstract: A flexible epoxy resin system is prepared by incorporating a combination of hardeners (A) and (B) in an epoxy resin, wherein the amounts of the two hardeners are varied to adjust the flexibility of the epoxy resin.Type: GrantFiled: June 4, 1996Date of Patent: July 29, 1997Assignee: Huels AktiengesellschaftInventors: Richard Braunstein, Bernhard Schleimer, Felix Schmitt, Joern Volker Weiss, Elmar Wolf
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Patent number: 5650477Abstract: Liquid reactive thermosetting compositions comprising:A) At least one polyepoxide or a mixture of one or more polyepoxides with at least one monoepoxide, of an aliphatic, cycloaliphatic or mixed nature;B) at least one anhydride of a di- or polycarboxylic acid of an aliphatic, cycloaliphatic or mixed nature;C) at least one catalyst capable of promoting the rapid polymerization of the mixture A+B under microwave irradiation and having general formula (I):N.tbd.C--CH.sub.2 --CH(Z)--(O).sub.r --Y.sup.+ NR.sub.1 R.sub.2 R.sub.3 X.sup.-.Type: GrantFiled: December 11, 1995Date of Patent: July 22, 1997Assignee: Enichem S.p.A.Inventors: Fabrizio Parodi, Renata Gerbelli, Mark DeMeuse
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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: 5623046Abstract: A self-dispersing curable epoxy composition is prepared upon contacting (a) 1.0 reactive equivalents of an epoxy resin, (b) between 0.005 and 0.5 reactive equivalents of an amine-epoxy adduct, and optionally (c) from about 0.01 to 1.0 reactive equivalents of a polyhydric phenol, wherein the amine-epoxy adduct is formed upon contacting 1.0 equivalents of an aliphatic polyepoxide and greater than 1.0 but no more than about 2.5 reactive equivalents of a polyoxyalkyleneamine. The self-dispersing curable epoxy resin forms an aqueous dispersion upon mixing with water. When cured, the dispersion is useful as a coating composition.Type: GrantFiled: June 7, 1995Date of Patent: April 22, 1997Assignee: Henkel CorporationInventors: John G. Papalos, Shailesh Shah, Reuben H. Grinstein, Joseph L. Mulvey, Brian G. Jewell
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Patent number: 5604269Abstract: A self-dispersing curable epoxy composition is prepared upon contacting (a) 1.0 reactive equivalents of an epoxy resin, (b) between 0.005 and 0.5 reactive equivalents of an amine-epoxy adduct, and optionally (c) from about 0.01 to 1.0 reactive equivalents of a polyhydric phenol, wherein the amine-epoxy adduct is formed upon contacting 1.0 equivalents of an aliphatic polyepoxide and greater than 1.0 but no more than about 2.5 reactive equivalents of a polyoxyalkyleneamine. The self-dispersing curable epoxy resin forms an aqueous dispersion upon mixing with water. When cured, the dispersion is useful as a coating composition.Type: GrantFiled: August 25, 1994Date of Patent: February 18, 1997Assignee: Henkel CorporationInventors: John G. Papalos, Shailesh Shah, Reuben H. Grinstein, Joseph L. Mulvey, Brian G. Jewell
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Patent number: 5599855Abstract: A new epoxy hardener composition is the product of the reaction of (A) a poly(alkylene oxide) monoamine or diamine with a molecular weight (Mn) of about 500 to 6000 and (B) a di- or polyepoxide, in a ratio of epoxide to active amine hydrogens of about 1.1:1 to 6:1 to yield an intermediate (C), which in a second step is reacted with (D) a di- or polyamine, in a ratio of active amine hydrogens to epoxide of greater than about 25 to 1, preferably greater than about 30 to 1. The compositions of the invention are excellent emulsifiers of liquid epoxy resins in aqueous medium without the addition of added surfactants or acidic compounds, and can be used to prepare water resistant water-borne coatings and related products from both liquid and solid epoxy resins, that possess long pot lives and contain relatively small amounts of volatile organic compounds.Type: GrantFiled: June 5, 1995Date of Patent: February 4, 1997Assignee: Air Products and Chemicals, Inc.Inventor: Frederick H. Walker
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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: 5585446Abstract: An epoxy resin composition is disclosed that contains compounds that contain at least two 1,2-epoxide groups. The epoxide group-containing compounds are reaction products of compounds (A1) that contain at least two 1,2-epoxide groups per molecule, compounds (A2) that are polyoxyalkylenemonoamines that have a molecular weight of from 130 to 900 and, if desired, polyoxyalkylenemonoamines (A3) that have a molecular weight of from 900 to 5000 and/or polycarboxylic acids (A4). The resin composition additionally contains at least one hardener (B) and, if desired, customary additives (C).Type: GrantFiled: December 12, 1994Date of Patent: December 17, 1996Assignee: Hoechst AktiengesellschaftInventors: Manfred Marten, Bernhard Wehner
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Patent number: 5578649Abstract: Disclosed herein are a process for producing an epoxy adhesive auxiliary which is a liquid reclaimed from rigid polyurethane foam and an epoxy adhesive which contains the auxiliary. The epoxy adhesive auxiliary can be produced, without requiring any special apparatus for purification, by incorporating rigid polyurethane foam (200 g) in powder form (5-10 mm in size) with glycol such as polyethylene glycol (100 g) and amino alcohol such as 2-aminoethanol (5 g), and heating them at 150.degree.-280.degree. C., thereby chemically decomposing the rigid polyurethane foam into a viscous liquid. This reclaimed liquid (50-300 g) is incorporated as such into an epoxy resin adhesive base such as bisphenol A-type epoxy resin (100 g), containing optional diethylamine (6-8 g). The resulting epoxy resin adhesive is superior in tensile shear bond strength.Type: GrantFiled: March 13, 1995Date of Patent: November 26, 1996Assignee: INOAC CorporationInventors: Yoshio Imai, He Fei-Feng, Xue Shu-Chang, Takao Hidai
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Patent number: 5567748Abstract: A water miscible or soluble amine terminated resin useful as a curing agent comprising the reaction product of: A) a polyamine component comprising one or more hydrophilic poly(oxyalkylene) amines, and optionally one or more hydrophobic polyamines; B) a polyepoxide component comprising one or more diglycidyl ethers of a polyalkylene glycol, one or more diglycidyl ethers of a cycloalkylene glycol and optionally one or more hydrophobic polyglycidyl ethers, wherein the mixture is optionally advanced by an amine extender; C) optionally, a reactive diluent which is capable of reacting with an epoxy resin, and D) optionally, a catalyst for the reaction of an amine with an epoxy resin; wherein Component A is employed in an equivalent excess with respect to Component B such that the terminal moieties of the reaction product are amine moieties capable of reacting with an epoxy resin; the composition has an amine hydrogen equivalent weight of from 140 to 240; and the composition is water soluble or water miscible.Type: GrantFiled: May 25, 1994Date of Patent: October 22, 1996Assignee: The Dow Chemical CompanyInventors: Dieter H. Klein, Hans J. Wessely
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Patent number: 5567792Abstract: A curing agent for epoxy resins is prepared from an amine and an epoxy, as well as subsequent modification by a polyisocyanate compound, in such a manner that the curing agent is in the form of small spherical particles. The particles can be as small as 0.1 microns. This curing agent can be easily dispersed in curing agent masterbatches and curable compositions with minimal effect on their storage stability. The resulting curable compositions have a wide range of applications, including automobile and electronic adhesives.Type: GrantFiled: June 7, 1995Date of Patent: October 22, 1996Assignee: W. R. Grace & Co.-Conn.Inventors: Souichi Muroi, Hsi-Chuan Tsai
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Patent number: 5565505Abstract: A self-dispersing curable epoxy composition is prepared upon contacting (a) 1.0 reactive equivalents of an epoxy resin, (b) from about 0.01 to 1.0 reactive equivalents of a polyhydric phenol, and (c) between 0.005 and 0.025 reactive equivalents of an amine-epoxy adduct, wherein the amine-epoxy adduct is formed upon contacting 1.0 equivalents of an aliphatic polyepoxide and between 0.3 and 0.9 reactive equivalents of a polyoxyalkyleneamine. The self-dispersing curable epoxy resin forms an aqueous dispersion upon mixing with water. When cured, the dispersion is useful as a coating composition.Type: GrantFiled: June 14, 1994Date of Patent: October 15, 1996Assignee: Henkel CorporationInventors: John G. Papalos, Reuben H. Grinstein, Shailesh Shah, Joseph L. Mulvey, Brian G. Jewell
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Patent number: 5565506Abstract: A self-dispersing curable epoxy composition is prepared upon contacting (a) 1.0 reactive equivalents of an epoxy resin, (b) from about 0.65 to 0.95 reactive equivalents of a polyhydric phenol, and (c) between 0.005 and 0.5 reactive equivalents of an amine-epoxy adduct, wherein the amine-epoxy adduct is formed upon contacting 1.0 equivalents of an aliphatic polyepoxide and between 0.3 and 0.9 reactive equivalents of a polyoxyalkyleneamine. The self-dispersing curable epoxy resin forms an aqueous dispersion upon mixing with water. When cured, the dispersion is useful as a coating composition.Type: GrantFiled: August 25, 1994Date of Patent: October 15, 1996Assignee: Henkel CorporationInventors: John G. Papalos, Reuben H. Grinstein, Shailesh Shah, Joseph L. Mulvey, Brian G. Jewell
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Patent number: 5561204Abstract: A curing agent for epoxy resins is prepared from an amine and an epoxy, as well as subsequent modification by a polyisocyanate compound, in such a manner that the curing agent is in the form of small spherical particles. The particles can be as small as 0.1 microns. This curing agent can be easily dispersed in curing agent masterbatches and curable compositions with minimal effect on their storage stability. The resulting curable compositions have a wide range of applications, including automobile and electronic adhesives.Type: GrantFiled: June 7, 1995Date of Patent: October 1, 1996Assignee: W. R. Grace & Co.-Conn.Inventors: Souichi Muroi, Hsi-Chuan Tsai
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Patent number: 5554714Abstract: A curing agent for epoxy resins is prepared from an amine and an epoxy, as well as subsequent modification by a polyisocyanate compound, in such a manner that the curing agent is in the form of small spherical particles. The particles can be as small as 0.1 microns. This curing agent can be easily dispersed in curing agent masterbatches and curable compositions with minimal effect on their storage stability. The resulting curable compositions have a wide range of applications, including automobile and electronic adhesives.Type: GrantFiled: June 7, 1995Date of Patent: September 10, 1996Assignee: W. R. Grace & Co.-Conn.Inventors: Souichi Muroi, Hsi-Chuan Tsai
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Patent number: 5554672Abstract: A primer comprises a liquid epoxy resin, a hydrophobic polyamine compound, a thixotropic agent and a silane coupling agent. After coating the primer on a wet concrete surface of a structure, a reinforced fiber sheet or similar material could be attached to the surface with a high level of adhesive strength without being influenced by the water. The reinforced fiber sheet is impregnated with a matrix resin and cured to achieve a satisfactory reinforcement of the concrete structure.Type: GrantFiled: March 17, 1994Date of Patent: September 10, 1996Assignee: Tonen CorporationInventors: Makoto Saito, Yoshimasa Chiba, Hiroyuki Misaki
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Patent number: 5548058Abstract: A curing agent for epoxy resins is prepared from an amine and an epoxy, as well as subsequent modification by a polyisocyanate compound, in such a manner that the curing agent is in the form of small spherical particles. The particles can be as small as 0.1 microns. This curing agent can be easily dispersed in curing agent masterbatches and curable compositions with minimal effect on their storage stability. The resulting curable compositions have a wide range of applications, including automobile and electronic adhesives.Type: GrantFiled: June 7, 1995Date of Patent: August 20, 1996Assignee: W. R. Grace & Co.-Conn.Inventors: Souichi Muroi, Hsi-Chuan Tsai
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Patent number: 5534565Abstract: Epoxy resin compositions used in preparation of laminates for electronic applications are free of the solvents typically needed in current industrial practice. The use of certain mono-substituted dicyandiamides makes possible the elimination of such solvents since all of the components are soluble in epoxy resin to an extent which provides uniform properties in the cured laminates.Type: GrantFiled: April 15, 1994Date of Patent: July 9, 1996Assignee: AlliedSignal Inc.Inventors: Joseph J. Zupancic, Jeffrey P. Conrad, Jiri D. Konicek, Aroon V. Tungare
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Patent number: 5525433Abstract: This invention relates to an adhesive composition, comprising: (A) at least one multifunctional epoxy; and (B) the composition derived from (B-1) at least one difunetional epoxy resin and (B-2) at least one compound represented by the formulaR--(G).sub.n (I)wherein in Formula (I): R is an aromatic, alicyclic or heterocyclic group; G is a functional group selected from the group consisting of COOH, OH, SH, NH.sub.2, NHR.sup.1, (NHC(.dbd.NH)).sub.m NH.sub.2, R.sup.2 COOH, R.sup.2 OH, R.sup.2 SH, R.sup.2 NH.sub.2 and R.sup.2 NHR.sup.1, wherein R.sup.1 is a hydrocarbon group, R.sup.2 is an alkylene or alkylidene group and m is a number in the range of 1 to about 4; and n is a number ranging from 3 up to the number of displaceable hydrogens on R; with the proviso that when at least one G is NH.sub.2 or R.sup.2 NH.sub.2, n is a number ranging from 2 up to the number of displaceable hydrogens on R, and when at least one G is (NHC(.dbd.NH)).sub.m NH.sub.Type: GrantFiled: June 6, 1995Date of Patent: June 11, 1996Assignee: Gould Electronics Inc.Inventors: Charles A. Poutasse, Katherine V. Sack, Andrea M. Kovacs, James R. Winchester
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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: 5489630Abstract: A new epoxy hardener composition is the product of the reaction of (A) a poly(alkylene oxide) monoamine or diamine with a molecular weight (Mn) of about 500 to 3000 and (B) a di- or polyepoxide, in a ratio of epoxide to active amine hydrogens of about 1.1:1 to 6:1 to yield an intermediate (C), which in a second step is reacted with (D) a di- or polyamine, in a ratio of active amine hydrogens to epoxide of greater than about 25 to 1, preferably greater than about 30 to 1. The compositions of the invention are excellent emulsifiers of liquid epoxy resins in aqueous medium without the addition of added surfactants or acidic compounds, and can be used to prepare water resistant water-borne coatings and related products from both liquid and solid epoxy resins, that possess long pot lives and contain relatively small amounts of volatile organic compounds.Type: GrantFiled: November 28, 1994Date of Patent: February 6, 1996Assignee: Air Products and Chemicals, Inc.Inventor: Frederick H. Walker
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Patent number: 5475039Abstract: A curing agent for aqueous epoxy resin emulsions comprising 10-80% by weight of at least one emulsifier, 1-80% by weight of at least one coemulsifier, and 5-80% by weight of at least one bis(diamine)-diepoxide adduct. Optionally, the curing agent contains 0-80% by weight of a diamine or a mixture of two or more diamines.Type: GrantFiled: October 17, 1994Date of Patent: December 12, 1995Assignee: Sika AG, vorm. Kaspar Winkler & Co.Inventor: Pierre-Andre Butikofer
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Patent number: 5464924Abstract: Polyaminoethers prepared by reacting (1) a primary amine or bis(secondary) diamine with (2) a diglyeidyl ether and (3) an amine- or epoxy-functionalized poly(alkylene oxide) exhibit a combination of low glass transition temperature (Tg of 14.degree. C. to 73.degree. C.) and low oxygen transmission rate (OTR of 0.53 to 19.0 cc-mil/100-in.sup.2 -atm-day).Type: GrantFiled: January 7, 1994Date of Patent: November 7, 1995Assignee: The Dow Chemical CompanyInventors: H. Craig Silvis, Shari L. Kram
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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: 5459208Abstract: An elastically-cured epoxy resin composition is disclosed that contains compounds that contain at least two 1,2-epoxide groups. The epoxide group-containing compounds are reaction products of compounds (A1) that contain at least two 1,2-epoxide groups per molecule, polyoxyalkylenemonoamines (A2) that have a molecular weight (number average) greater than 900 g/mol, and optionally polycarboxylic acids (A3). The polyoxyalkylenemonoamines (A2) are polyoxypropylenemonoamines which preferably contain a mole fraction of up to 20% of oxyethylene units based on the total amount of oxypropylene and oxyethylene units. The resin composition additionally contains at least one hardener (B) and, if desired, customary additives (C).Type: GrantFiled: December 12, 1994Date of Patent: October 17, 1995Assignee: Hoechst AktiengesellschaftInventors: Manfred Marten, Bernhard Wehner
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Patent number: 5422042Abstract: This invention discloses the composition and preparation of imidazolidone modified polyetheramines. The alkyl polyetheramine is derived from 2-isopropylaminoethylamine and urea. N-isopropyl-2-imidazolidone is the intermediate product, which is alkoxylated and aminated to prepare the N-isopropyl imidazolidone polyetheramine. This invention also discloses the composition and preparation of oxazolidinone modified polyetheramines by reductive amination of polyols derived from 4-ethyl-4-hydroxymethyl-2-oxazolidone. The products of this invention have been tested in epoxy resin applications and improved properties have been demonstrated. These products may also be useful in polyurea applications.Type: GrantFiled: November 19, 1993Date of Patent: June 6, 1995Assignee: Huntsman CorporationInventors: Waddill: Harold G., Wei-Yang Su, Michael Cuscurida, Terry L. Renken
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Patent number: 5420172Abstract: Cross-linked epoxy resins having nonlinear optical properties may be used in nonlinear optical media. These cross-linked epoxy resins may have the following structure: ##STR1## Z.sup.1 and Z.sup.2 being NLO-chromophores.Type: GrantFiled: August 23, 1993Date of Patent: May 30, 1995Assignee: Siemens AktiengesellschaftInventors: Jens Nordmann, Rainer Puehl
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Patent number: 5395911Abstract: A thermally curable mixture contains 10-70% by weight of reactive compounds, 0.05-2% by weight of at least one basic catalyst, and at least one solvent. The reactive compounds are consisting essentially of a first reactive compound and a second reactive compound at a molar ratio between 1:1 and 1:10. The first reactive compound is a formamide selected from the group consisting of hydroxyformamides, di-formamides and polyformamides, and the second reactive compound is at least one compound having an epoxy equivalent between 100 and 800 g KOH per mole epoxy group, selected from a group of aromatic di-glycidylethers and aromatic poly-glycidylethers. The basic catalyst is at least one chemical agent selected from the group consisting of tertiary ammonium salts, tertiary aromatic amines, and tertiary heterocyclic amines. The solvent is at least one chemical compound selected from the group consisting of aliphatic alcohols, ether alcohols, diether, and tertiary amides.Type: GrantFiled: July 19, 1993Date of Patent: March 7, 1995Assignee: Dainippon Ink and Chemicals, Inc.Inventors: Rainer B. Frings, Gerwald F. Grahe
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Patent number: 5357008Abstract: A latent curing agent for epoxy resins in the form of finely divided particles is disclosed, along with its method of preparation. An amine/epoxy adduct is formed in small particles with an encapsulating layer of polyfunctional epoxy or isocyanate on the surface by an emulsion precipitation method.Type: GrantFiled: January 14, 1993Date of Patent: October 18, 1994Assignee: W. R. Grace & Co.-Conn.Inventors: Hsi-Chuan Tsai, Souichi Muroi
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Patent number: 5344897Abstract: Liquid coating agent based on a polymer containing acetoacetate groups and a polyamine in the form of the corresponding aldimine or ketimine, the polymer containing acetoacetate groups being obtained by reaction of a polyepoxide with water, an amine or a hydroxycarboxylic acid and subsequent esterification or transesterification with acetoacetic acid. These liquid coating agents are particularly suitable as binders in two-component automobile repair fillers or as two-component primers.Type: GrantFiled: October 29, 1993Date of Patent: September 6, 1994Assignee: Hoechst AGInventors: Gerhard Brindoepke, Uwe Kubillus, Helmut Plum
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Patent number: 5340889Abstract: Liquid hydroxyurethane products having cyclocarbonate end groups are prepared by reacting a molar excess of a bis-carbonate of a bis-glycidyl ether of neopentyl glycol or 1,4-cyclohexanedimethanol with a polyoxyalkylenediamine such as a polyoxypropylenediamine. These products are useful for the preparation of polyurethanes, polyurethane polyols, polyester polyurethane polyols, and polycarbonate polyurethane polyols.Type: GrantFiled: July 19, 1993Date of Patent: August 23, 1994Assignee: Texaco Chemical CompanyInventors: Wheeler C. Crawford, Edward T. Marquis, Howard P. Klein
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Patent number: 5338782Abstract: A composition comprising a 1,2-dialkylidenecyclobutane such as 1,2-dimethylenecyclobutane, a polyimide such as a bismaleimide, an epoxy resin and a curing agent for the epoxy resin can be thermally cured to a tough polymer blend having a high glass transition temperature.Type: GrantFiled: May 27, 1993Date of Patent: August 16, 1994Assignee: Shell Oil CompanyInventor: Larry S. Corley
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Patent number: 5332785Abstract: A liquid coating composition based on a polymer containing acetoacetate groups and a polyamine in the form of the corresponding aldimine or ketimine, the polymer containing acetoacetate groups being obtained by reacting a polyepoxide containing hydroxyl groups, or a polyepoxide which is partially or completely reacted with monocarboxylic acids, with acetoacetic acid derivatives. These liquid coating compositions are suitable in particular as binders in two-component fillers for automotive refinishing or as two-component primers.Type: GrantFiled: March 29, 1993Date of Patent: July 26, 1994Assignee: Hoechst AktiengesellschaftInventor: Gerhard Brindoepke
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Patent number: 5319004Abstract: Hardeners for epoxy resins, comprising reaction products of(A) polyamidoamines that were obtained by polycondensation of (a) dicarboxylic acids containing oxyalkylene groups, or their derivatives, with (b) polyamines containing at least two amino groups capable of undergoing condensation with (a),(B) polyamines containing at least two secondary amino groups, and(C) adducts of (c) polyepoxy compounds and (d) polyalkylene polyether polyols.Epoxy resins that have been cured with these hardeners exhibit in particular a very good water resistance.Type: GrantFiled: February 26, 1993Date of Patent: June 7, 1994Assignee: Hoechst AktiengesellschaftInventors: Manfred Marten, Bernhard Stengel-Rutkowski, Claus Godau
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Patent number: 5318851Abstract: Curable compositions which are precursors for cured or partially cured light stabilized epoxy resins which are the product of the reaction of some or all of the epoxy groups of an epoxy resin with an N-(2,2,6,6-tetraalkyl-4-piperidinyl)amic acid hydrazide as well as the cured or partially cured reaction products thereof together with processes for their use and articles of manufacture produced thereby are disclosed.Type: GrantFiled: April 2, 1993Date of Patent: June 7, 1994Assignee: Elf Atochem N.A., Inc.Inventors: Arthur L. Baron, Ronald E. MacLeay, Jennifer P. Kmiec
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Patent number: 5317050Abstract: Compositions containing an aryl phosphite and water to hydrolyze the aryl phosphite provide controlled and extended work time when used as hardening agents for the ambient temperature hardening of phenolic resins and for rapid hardening of such resins at modestly elevated temperatures. Pre-solvolysis with small quantities of water, alkanols of 1 to 4 carbon atoms or alkylene glycols of 2 to 4 carbon atoms improve compatibility of trisubstituted phosphites with the resin. Pre-hydrolysis of the phosphites as well as addition of furfuryl alcohol or alkylene glycols of 2 to 4 carbon atoms accelerate the hardening (curing) of the resin. Various compounds such as: carboxylic acid amides, urea, dicyandiamide, N-methylolated amides, N-alkyl 2-pyrrolidinones having 1 to 4 carbon atoms in the alkyl group, those having an internal epoxide group, alkanols, and Schiff bases retard the ambient temperature hardening of the resin with the aryl phosphite hardening agents.Type: GrantFiled: December 13, 1993Date of Patent: May 31, 1994Assignee: Borden, Inc.Inventor: Arthur H. Gerber
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Patent number: 5300584Abstract: A low viscosity, diprimary amine-terminated reactive liquid polymer with low residual amine content, comprising the reaction product of a diprimary amine having the following formulaH.sub.2 N--R--NH.sub.2wherein --NH.sub.2 is a primary terminal amine group; andwherein R is(1) a C.sub.4 -C.sub.12 aliphatic chain having alkyl branches containing 2 to 4 carbons, wherein the positions of said alkyl branches within the C.sub.4 -C.sub.12 aliphatic chain are such that they impart relatively different rates of reactivity to the terminal primary amine groups; or(2) a carbon to carbon backbone containing at least one non-reactive heteroatom, comprising(a) a C.sub.2 -C.sub.20 aliphatic or cycloaliphatic moiety containing at least one tertiary amine; or(b) a polyoxyalkylene wherein the alkyl portion of said polyoxyalkylene contains 2 to 4 carbon atoms;and a functional-terminated reactive liquid polymer useful as an epoxy resin modifier employed with a curing agent.Type: GrantFiled: September 17, 1992Date of Patent: April 5, 1994Assignee: The B. F. Goodrich CompanyInventor: Julius Farkas
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Patent number: 5300559Abstract: Polyamines endowed with chain extension activity for formulations such as polyureas and polyurethanes are disclosed, which have the general formula: ##STR1## wherein n is 0-1000; R.sub.1 =R.sub.2, and R.sub.1 and R.sub.2 are from the group --CH.sub.2 --CH.sub.2 --; --CH.sub.2 --C(CH.sub.3)H--; and --C(CH.sub.3)H--CH.sub.2 --; and R.sub.3 and R.sub.4 are each independently selected from the group consisting of H, --CH.sub.3, --CH.sub.2 CH.sub.3, --CH.sub.2 OH, and --CH.sub.2 --CH.sub.2 --OH.Type: GrantFiled: May 28, 1993Date of Patent: April 5, 1994Assignee: Hoechst Celanese CorporationInventors: Michael T. Sheehan, James R. Sounik
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Patent number: 5298538Abstract: Plasticizing resins, aqueous dispersions of cationic resins, and methods of making the same for use in cathodic electrodeposition are disclosed. The resins are formed from reacting a polyoxyalkylenepolyamine, a phenol, and a formaldehyde. The reactants may further include a block building unit derived from a polyepoxide. When used in combination with other conventional electrodepositable resins, deposited films with improved mechanical properties and descreased tendency toward cratering are obtained.Type: GrantFiled: April 11, 1990Date of Patent: March 29, 1994Assignee: BASF CorporationInventors: Klaus Cibura, Yali F. Hallock, John A. Gilbert, John D. McGee
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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