Nitrogen-containing Alcohol, Inorganic Alcoholate, Or Ether Patents (Class 528/111)
  • Patent number: 5874490
    Abstract: 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: Grant
    Filed: October 30, 1996
    Date of Patent: February 23, 1999
    Assignee: Henkel Corporation
    Inventors: Kartar S. Arora, John G. Papalos, Grannis S. Johnson
  • Patent number: 5855961
    Abstract: 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: Grant
    Filed: May 12, 1997
    Date of Patent: January 5, 1999
    Assignee: Vianova Resins GmbH
    Inventors: Michael Hoenel, Armin Pfeil, Thomas Budnick, Heiner Schwan
  • Patent number: 5834620
    Abstract: 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: Grant
    Filed: November 14, 1997
    Date of Patent: November 10, 1998
    Assignee: University of Liverpool
    Inventors: Geoffrey Charles Eastmond, Jerzy Paprotny
  • Patent number: 5798398
    Abstract: 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: Grant
    Filed: October 18, 1996
    Date of Patent: August 25, 1998
    Assignee: Henkel Corporation
    Inventors: Shailesh Shah, Ronald J. Cash, Ronald LaFreeda, James Aloye, Joseph L. Mulvey
  • Patent number: 5763506
    Abstract: 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: Grant
    Filed: September 26, 1996
    Date of Patent: June 9, 1998
    Assignee: Henkel Corporation
    Inventors: John G. Papalos, Reuben H. Grinstein, Shailesh Shah, Joseph L. Mulvey, Brian G. Jewell
  • Patent number: 5760108
    Abstract: 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: Grant
    Filed: October 22, 1996
    Date of Patent: June 2, 1998
    Assignee: Henkel Corporation
    Inventors: Kartar S. Arora, Grannis S. Johnson, James Aloye
  • Patent number: 5723565
    Abstract: 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: Grant
    Filed: April 12, 1993
    Date of Patent: March 3, 1998
    Assignee: Huntsman Petrochemical Corporation
    Inventors: Michael Cuscurida, Kathy Beth Sellstrom
  • Patent number: 5707702
    Abstract: 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: Grant
    Filed: June 26, 1996
    Date of Patent: January 13, 1998
    Inventors: Robert F. Brady, Jr., James D. Adkins
  • Patent number: 5681907
    Abstract: 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: Grant
    Filed: January 4, 1996
    Date of Patent: October 28, 1997
    Assignee: Air Products and Chemicals, Inc.
    Inventors: William Edward Starner, John Anthony Marsella, Lloyd Gerald Easterday
  • Patent number: 5652323
    Abstract: 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: Grant
    Filed: June 6, 1995
    Date of Patent: July 29, 1997
    Assignee: Henkel Corporation
    Inventors: John G. Papalos, Reuben H. Grinstein, Shailesh Shah, Joseph L. Mulvey, Brian G. Jewell
  • Patent number: 5652318
    Abstract: 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: Grant
    Filed: June 4, 1996
    Date of Patent: July 29, 1997
    Assignee: Huels Aktiengesellschaft
    Inventors: Richard Braunstein, Bernhard Schleimer, Felix Schmitt, Joern Volker Weiss, Elmar Wolf
  • Patent number: 5650477
    Abstract: 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: Grant
    Filed: December 11, 1995
    Date of Patent: July 22, 1997
    Assignee: Enichem S.p.A.
    Inventors: Fabrizio Parodi, Renata Gerbelli, Mark DeMeuse
  • Patent number: 5631332
    Abstract: 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: Grant
    Filed: January 11, 1996
    Date of Patent: May 20, 1997
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Minato Karasawa, Takuji Shimizu
  • Patent number: 5623046
    Abstract: 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: Grant
    Filed: June 7, 1995
    Date of Patent: April 22, 1997
    Assignee: Henkel Corporation
    Inventors: John G. Papalos, Shailesh Shah, Reuben H. Grinstein, Joseph L. Mulvey, Brian G. Jewell
  • Patent number: 5604269
    Abstract: 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: Grant
    Filed: August 25, 1994
    Date of Patent: February 18, 1997
    Assignee: Henkel Corporation
    Inventors: John G. Papalos, Shailesh Shah, Reuben H. Grinstein, Joseph L. Mulvey, Brian G. Jewell
  • Patent number: 5599855
    Abstract: 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: Grant
    Filed: June 5, 1995
    Date of Patent: February 4, 1997
    Assignee: Air Products and Chemicals, Inc.
    Inventor: Frederick H. Walker
  • Patent number: 5591812
    Abstract: 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: Grant
    Filed: January 26, 1996
    Date of Patent: January 7, 1997
    Assignee: Air Products and Chemicals, Inc.
    Inventor: William E. Starner
  • Patent number: 5585446
    Abstract: 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: Grant
    Filed: December 12, 1994
    Date of Patent: December 17, 1996
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Manfred Marten, Bernhard Wehner
  • Patent number: 5578649
    Abstract: 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: Grant
    Filed: March 13, 1995
    Date of Patent: November 26, 1996
    Assignee: INOAC Corporation
    Inventors: Yoshio Imai, He Fei-Feng, Xue Shu-Chang, Takao Hidai
  • Patent number: 5567748
    Abstract: 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: Grant
    Filed: May 25, 1994
    Date of Patent: October 22, 1996
    Assignee: The Dow Chemical Company
    Inventors: Dieter H. Klein, Hans J. Wessely
  • Patent number: 5567792
    Abstract: 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: Grant
    Filed: June 7, 1995
    Date of Patent: October 22, 1996
    Assignee: W. R. Grace & Co.-Conn.
    Inventors: Souichi Muroi, Hsi-Chuan Tsai
  • Patent number: 5565505
    Abstract: 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: Grant
    Filed: June 14, 1994
    Date of Patent: October 15, 1996
    Assignee: Henkel Corporation
    Inventors: John G. Papalos, Reuben H. Grinstein, Shailesh Shah, Joseph L. Mulvey, Brian G. Jewell
  • Patent number: 5565506
    Abstract: 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: Grant
    Filed: August 25, 1994
    Date of Patent: October 15, 1996
    Assignee: Henkel Corporation
    Inventors: John G. Papalos, Reuben H. Grinstein, Shailesh Shah, Joseph L. Mulvey, Brian G. Jewell
  • Patent number: 5561204
    Abstract: 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: Grant
    Filed: June 7, 1995
    Date of Patent: October 1, 1996
    Assignee: W. R. Grace & Co.-Conn.
    Inventors: Souichi Muroi, Hsi-Chuan Tsai
  • Patent number: 5554714
    Abstract: 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: Grant
    Filed: June 7, 1995
    Date of Patent: September 10, 1996
    Assignee: W. R. Grace & Co.-Conn.
    Inventors: Souichi Muroi, Hsi-Chuan Tsai
  • Patent number: 5554672
    Abstract: 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: Grant
    Filed: March 17, 1994
    Date of Patent: September 10, 1996
    Assignee: Tonen Corporation
    Inventors: Makoto Saito, Yoshimasa Chiba, Hiroyuki Misaki
  • Patent number: 5548058
    Abstract: 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: Grant
    Filed: June 7, 1995
    Date of Patent: August 20, 1996
    Assignee: W. R. Grace & Co.-Conn.
    Inventors: Souichi Muroi, Hsi-Chuan Tsai
  • Patent number: 5534565
    Abstract: 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: Grant
    Filed: April 15, 1994
    Date of Patent: July 9, 1996
    Assignee: AlliedSignal Inc.
    Inventors: Joseph J. Zupancic, Jeffrey P. Conrad, Jiri D. Konicek, Aroon V. Tungare
  • Patent number: 5525433
    Abstract: 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: Grant
    Filed: June 6, 1995
    Date of Patent: June 11, 1996
    Assignee: Gould Electronics Inc.
    Inventors: Charles A. Poutasse, Katherine V. Sack, Andrea M. Kovacs, James R. Winchester
  • Patent number: 5508373
    Abstract: 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: Grant
    Filed: August 4, 1994
    Date of Patent: April 16, 1996
    Assignee: Henkel Corporation
    Inventors: Shailesh Shah, Robert M. Moon
  • Patent number: 5489630
    Abstract: 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: Grant
    Filed: November 28, 1994
    Date of Patent: February 6, 1996
    Assignee: Air Products and Chemicals, Inc.
    Inventor: Frederick H. Walker
  • Patent number: 5475039
    Abstract: 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: Grant
    Filed: October 17, 1994
    Date of Patent: December 12, 1995
    Assignee: Sika AG, vorm. Kaspar Winkler & Co.
    Inventor: Pierre-Andre Butikofer
  • Patent number: 5464924
    Abstract: 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: Grant
    Filed: January 7, 1994
    Date of Patent: November 7, 1995
    Assignee: The Dow Chemical Company
    Inventors: H. Craig Silvis, Shari L. Kram
  • Patent number: 5459204
    Abstract: 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: Grant
    Filed: March 7, 1994
    Date of Patent: October 17, 1995
    Assignee: Huels Aktiengesellschaft
    Inventors: Rainer Lomoelder, Wilfried Paulen, Felix Schmitt, Elmar Wolf
  • Patent number: 5459208
    Abstract: 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: Grant
    Filed: December 12, 1994
    Date of Patent: October 17, 1995
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Manfred Marten, Bernhard Wehner
  • Patent number: 5422042
    Abstract: 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: Grant
    Filed: November 19, 1993
    Date of Patent: June 6, 1995
    Assignee: Huntsman Corporation
    Inventors: Waddill: Harold G., Wei-Yang Su, Michael Cuscurida, Terry L. Renken
  • Patent number: 5420172
    Abstract: 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: Grant
    Filed: August 23, 1993
    Date of Patent: May 30, 1995
    Assignee: Siemens Aktiengesellschaft
    Inventors: Jens Nordmann, Rainer Puehl
  • Patent number: 5395911
    Abstract: 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: Grant
    Filed: July 19, 1993
    Date of Patent: March 7, 1995
    Assignee: Dainippon Ink and Chemicals, Inc.
    Inventors: Rainer B. Frings, Gerwald F. Grahe
  • Patent number: 5357008
    Abstract: 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: Grant
    Filed: January 14, 1993
    Date of Patent: October 18, 1994
    Assignee: W. R. Grace & Co.-Conn.
    Inventors: Hsi-Chuan Tsai, Souichi Muroi
  • Patent number: 5344897
    Abstract: 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: Grant
    Filed: October 29, 1993
    Date of Patent: September 6, 1994
    Assignee: Hoechst AG
    Inventors: Gerhard Brindoepke, Uwe Kubillus, Helmut Plum
  • Patent number: 5340889
    Abstract: 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: Grant
    Filed: July 19, 1993
    Date of Patent: August 23, 1994
    Assignee: Texaco Chemical Company
    Inventors: Wheeler C. Crawford, Edward T. Marquis, Howard P. Klein
  • Patent number: 5338782
    Abstract: 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: Grant
    Filed: May 27, 1993
    Date of Patent: August 16, 1994
    Assignee: Shell Oil Company
    Inventor: Larry S. Corley
  • Patent number: 5332785
    Abstract: 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: Grant
    Filed: March 29, 1993
    Date of Patent: July 26, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Gerhard Brindoepke
  • Patent number: 5319004
    Abstract: 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: Grant
    Filed: February 26, 1993
    Date of Patent: June 7, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Manfred Marten, Bernhard Stengel-Rutkowski, Claus Godau
  • Patent number: 5318851
    Abstract: 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: Grant
    Filed: April 2, 1993
    Date of Patent: June 7, 1994
    Assignee: Elf Atochem N.A., Inc.
    Inventors: Arthur L. Baron, Ronald E. MacLeay, Jennifer P. Kmiec
  • Patent number: 5317050
    Abstract: 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: Grant
    Filed: December 13, 1993
    Date of Patent: May 31, 1994
    Assignee: Borden, Inc.
    Inventor: Arthur H. Gerber
  • Patent number: 5300584
    Abstract: 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: Grant
    Filed: September 17, 1992
    Date of Patent: April 5, 1994
    Assignee: The B. F. Goodrich Company
    Inventor: Julius Farkas
  • Patent number: 5300559
    Abstract: 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: Grant
    Filed: May 28, 1993
    Date of Patent: April 5, 1994
    Assignee: Hoechst Celanese Corporation
    Inventors: Michael T. Sheehan, James R. Sounik
  • Patent number: 5298538
    Abstract: 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: Grant
    Filed: April 11, 1990
    Date of Patent: March 29, 1994
    Assignee: BASF Corporation
    Inventors: Klaus Cibura, Yali F. Hallock, John A. Gilbert, John D. McGee
  • Patent number: 5296570
    Abstract: 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: Grant
    Filed: June 1, 1993
    Date of Patent: March 22, 1994
    Assignee: The Dow Chemical Company
    Inventors: Jimmy D. Earls, Robert E. Hefner, Jr., Paul M. Puckett