Contains Nitrogen Atom Patents (Class 525/526)
  • Patent number: 6417316
    Abstract: Curable epoxy resin compositions, which are obtainable by heating a composition containing at least one epoxy compound, which contains on average at least one, preferably more than one, 1,2-epoxy group and optionally also one or several hydroxyl groups in the molecule, in the presence of at least one Lewis acid as catalyst, wherein the Lewis acid is a salt of trifluoromethanesulfonic acid or of perchloric acid, the counterion of which carries a 2- to 6-fold positive charge, until the epoxy value, measured in equivalent epoxy/kg (Eq/kg) of the starting material, has been reduced by 1 to 60 percent, preferably by 5 to 50 percent; a process for their preparation, and their use for the preparation of fully cured moulded compositions or coatings.
    Type: Grant
    Filed: October 19, 1999
    Date of Patent: July 9, 2002
    Assignee: Vantico Inc.
    Inventors: Rolf Wiesendanger, Walter Fischer
  • Patent number: 6410658
    Abstract: A curing agent for epoxy resin comprises: a) a reaction product of at least one polyalkylene polyether monoamine and/or polyamine with a polyepoxide and, optionally, a monoepoxide to obtain an epoxide group-containing precursor, the precursor further reacted with a primary monoamine and/or a primary or secondary polyamine in at least a 10% molar excess relative to the epoxide groups of the precursor, the reaction product being substantially free of non-reacted amines; b) an amine-terminated adduct of an epoxy resin and a primary monoamine and/or a primary or secondary polyamine being substantially free of non-reacted amines; and c) an amine-terminated adduct of an epoxide group-containing reactive thinning agent and a primary monoamine and/or a primary or secondary polyamine being substantially free of non-reacted amines.
    Type: Grant
    Filed: May 9, 2001
    Date of Patent: June 25, 2002
    Assignee: Bakelite AG
    Inventors: Markus Schrötz, Martin Fulgraff, Peter Martischewski, Jurgen Schillgalies, Rolf Herzog
  • Publication number: 20020072576
    Abstract: The invention relates to curing agents emulsifiable in water, which comprise the following components:
    Type: Application
    Filed: February 11, 2002
    Publication date: June 13, 2002
    Applicant: Bakelite AG
    Inventors: Markus Schrotz, Martin Fulgraff, Peter Martischewski, Jurgen Schillgalies, Rolf Herzog
  • Publication number: 20020072575
    Abstract: The invention relates to curing agents emulsifiable in water, which comprise the following components:
    Type: Application
    Filed: February 11, 2002
    Publication date: June 13, 2002
    Applicant: Bakelite AG
    Inventors: Markus Schrotz, Martin Fulgraff, Peter Martischewski, Jurgen Schillgalies, Rolf Herzog
  • Patent number: 6361879
    Abstract: A sealed semiconductor chip having a surface film of a sealed resin composition, wherein the resin composition has a linear expansion coefficient of 60×10−6/K or less at a temperature equal to or less than its glass transition point and 140×10−6/K or less at a temperature equal to or higher than its glass transition point; a semiconductor-sealing resin composition for sealing a semiconductor chip, which has a linear expansion coefficient of 60×10−6/K or less at a temperature equal to or less than its glass transition point and 140×10−6/K or less at a temperature equal to or higher than its glass transition point; the sealed semiconductor chip is chip size and has high reliability; the semiconductor-sealing resin composition creates a good seal on chip wafers and has high reliability; and the chip wafers sealed with a surface film of the resin composition warp little.
    Type: Grant
    Filed: September 23, 1999
    Date of Patent: March 26, 2002
    Assignees: Toray Industries, Inc., Fujitsu Limited
    Inventors: Yasuaki Tsutsumi, Masayuki Tanaka, Toshimi Kawahara, Yukio Takigawa
  • Patent number: 6355763
    Abstract: The invention relates to curable mixtures based on epoxy resins and aminic hardeners and cure accelerators, and, optionally solvents, plasticisers, UV stabilisers, dyes, pigments and/or fillers, wherein there is used as cure accelerator from 1 to 20% by weight, based on epoxy resin, of at least one heterocyclic compound of the general formula (I) wherein R1, R2 and R3, which may be the same or different, are —(CH2)a—N—[(CH2)b—CH3]2 radicals in which a=2 or 3 and b=0 or 1.
    Type: Grant
    Filed: December 2, 1999
    Date of Patent: March 12, 2002
    Assignee: Vantico GmbH & Co. KG
    Inventors: Wolfgang Scherzer, Jörg Volle
  • Patent number: 6353080
    Abstract: A flame retardant epoxy resin composition containing not more than 10% by wgt. of halogen, comprising an epoxy resin, stated concentrations of phosphoric acid ester, nitrogen—containing cross-linking agent having an amine functionality of at least 2 and a catalyst capable of promoting the reaction of the phosphoric acid ester with the epoxy resin and promoting the curing of the epoxy resin with the cross-linker, and optionally a Lewis acid in a stated amount.
    Type: Grant
    Filed: March 20, 2000
    Date of Patent: March 5, 2002
    Assignee: The Dow Chemical Company
    Inventors: Joseph Gan, Alan Goodson, Raymond A. Koenig, John P. Everett
  • Patent number: 6353079
    Abstract: The present invention concerns hydroxyaliphatic functional diglycidyl ethers of bisphenols (epoxy resins); curable (thermosettable) mixtures of at least one hydroxyaliphatic functional epoxy resin and at least one curing agent and/or catalyst therefor, as well as cured (thermoset) compositions prepared therefrom; and derivatives prepared therefrom. The bisphenol precursor to the diglycidyl ether contains a hydroxyaliphatic group linkage between the two aromatic rings of the bisphenol.
    Type: Grant
    Filed: July 26, 2000
    Date of Patent: March 5, 2002
    Assignee: The Dow Chemical Company
    Inventors: Louis L. Walker, Robert E. Hefner, Jr., Katherine S. Clement
  • Patent number: 6350825
    Abstract: An epoxy resin mixture is prepared by a) the reaction of (i) a diglycidyl compound, (ii) a bisphenol compound and (iii) at least one monophenol at temperatures of from 160 to 170° C. in the presence of an advancement catalyst that can be thermally deactivated, (b) upon completion of the reaction, the catalyst is deactivated by heating to a temperature of approximately 180° C. wherein (A1) one or more epoxy resins having an epoxy functionality of greater than two is added, and c) the resulting epoxy resin mixture is homogenized at that temperature.
    Type: Grant
    Filed: June 28, 2000
    Date of Patent: February 26, 2002
    Assignee: Vantico Inc.
    Inventors: Jürgen Finter, Isabelle Frischinger, Christine Poget
  • Patent number: 6337384
    Abstract: A method of making a thermally-removable epoxy by mixing a bis(maleimide) compound to a monomeric furan compound containing an oxirane group to form a di-epoxy mixture and then adding a curing agent at temperatures from approximately room temperature to less than approximately 90° C. to form a thermally-removable epoxy. The thermally-removable epoxy can be easily removed within approximately an hour by heating to temperatures greater than approximately 90° C. in a polar solvent. The epoxy material can be used in protecting electronic components that may require subsequent removal of the solid material for component repair, modification or quality control.
    Type: Grant
    Filed: January 18, 2000
    Date of Patent: January 8, 2002
    Assignee: Sandia Corporation
    Inventors: Douglas A. Loy, David R. Wheeler, Edward M. Russick, James R. McElhanon, Randall S. Saunders
  • Patent number: 6333064
    Abstract: A heat curable thermosetting epoxy resin formulation useful for making prepregs and electrical laminates containing a viscosity modifier, wherein the viscosity modifier is: (a) an optionally substituted polymer of a monovinylidene aromatic monomer, optionally having one or more further unsaturated monomers copolymerized therewith; (b) an optionally substituted polyphenylene oxide; or (c) an oxazolidone ring-containing compound.
    Type: Grant
    Filed: August 6, 1999
    Date of Patent: December 25, 2001
    Assignee: The Dow Chemical Company
    Inventor: Joseph Gan
  • Patent number: 6329473
    Abstract: Epoxy resin compositions comprising polyepoxides having at least two 1,2-epoxide groups, which can be obtained by reaction of diepoxides or polyepoxides or mixtures thereof with monoepoxides, and one or more amines sterically hindered amines, such as disecondary polyoxyalkylenediamines, and/or diprimary diamines, if desired with the addition of further 1,2-epoxide compounds and also hardeners, and use thereof as a coating for crack bridging, as an adhesive and in powder surface coatings.
    Type: Grant
    Filed: March 23, 1995
    Date of Patent: December 11, 2001
    Assignee: Solutia Germany GmbH & Co., KG
    Inventors: Manfred Marten, Claus Godau
  • Patent number: 6309757
    Abstract: Gas barrier coating compositions are provided which include a polyamine component, a polyepoxide component and a hydroxy-substituted aromatic compound that is present in an amount sufficient to provide a gas barrier coating having an oxygen permeability less than or equal to 75 percent of the oxygen permeability of the same composition without a hydroxy-substituted aromatic compound. Also provided is a multi-layer packaging material having at least one gas permeable packaging material layer and at least one gas barrier material layer formed from the gas barrier coating composition. Sealable containers are also provided.
    Type: Grant
    Filed: February 16, 2000
    Date of Patent: October 30, 2001
    Assignee: PPG Industries Ohio, inc.
    Inventors: Leland H. Carlblom, Cynthia Kutchko, Ken W. Niederst
  • Patent number: 6309751
    Abstract: To a substrate such as brass is applied a powder coating comprising a) at least one non-crystalline epoxy resin, b) at least one crystalline epoxy resin such as tetramethylbisphenol diglycidyl ether in an amount sufficient to reduce or eliminate bubble entrapment within the cured coating when cured at a temperature of below about 350° F. (about 177° C.), and c) a curing agent such as dicyandiamide.
    Type: Grant
    Filed: June 28, 2000
    Date of Patent: October 30, 2001
    Assignee: Rohm and Haas Company
    Inventors: William G. Ruth, Stacy L. Greth, Carryll A. Seelig, Dean A. Schreffler
  • Patent number: 6277930
    Abstract: The present invention relates to an epoxy resin composition used for cap seal of a hard disc drive spindle motor, which hardly causes outgassing even when using in a hard disc for high-speed rotation and has high reliability. The composition comprises an epoxy resin having at least one glycidyl group in a molecule as a component (A), a monomer having at least one unsaturated bond group in a molecule (polyfunctional vinyl monomer or monofunctional vinyl monomer) as a component (B), an epoxy resin curing agent as a component (C), a photopolymerization initiator as a component (D), and a partially-esterified unsaturated epoxy resin wherein 10-90% of an epoxy equivalent of a bisphenol type epoxy resin is (meth)acrylated as a component (E).
    Type: Grant
    Filed: August 4, 1999
    Date of Patent: August 21, 2001
    Assignee: Loctite Corporation
    Inventor: Katsue Nishikawa
  • Patent number: 6268409
    Abstract: The invention relates to a binder (A) in aqueous dispersion which is obtainable by neutralization of the tertiary amino groups of an amino-epoxy resin a1) with acid and reaction of the resulting product with a polyepoxide a2) to form quaternary ammonium groups and conversion into an aqueous dispersion with water. The invention furthermore relates to a process for the preparation of binders (A) in aqueous dispersion and their use in cathodic electrodeposition lacquers.
    Type: Grant
    Filed: September 17, 1999
    Date of Patent: July 31, 2001
    Assignee: Herberts GmbH & Co. KG
    Inventors: Klausjörg Klein, Helmut Hönig
  • Patent number: 6255409
    Abstract: An epoxy resin composition comprising (A) a bifunctional crystalline epoxy compound, (B) an amorphous trisphenolmethane type epoxy compound having three or more of epoxy groups in a molecule, and (C) an epoxy curing agent having phenolic hydroxyl groups. The resin composition has an excellent moldability (low viscosity and can be filled with filler with high density) and high softening point, and is used preferably as an encapsulating material for electronic device.
    Type: Grant
    Filed: March 12, 1999
    Date of Patent: July 3, 2001
    Assignee: Sumitomo Chemical Co., Ltd.
    Inventors: Yoshiki Matsuoka, Yasuhiro Hirano, Nobuyuki Nakajima
  • Patent number: 6248204
    Abstract: The present invention provides a room-temperature curable, reinforced thermosetting epoxy resin composition. The composition includes an epoxy resin first component, and an epoxy resin hardener second component. The epoxy resin component includes an epoxy resin, and may further include an inorganic and/or organic filler component, such as a structural reinforcement component. The epoxy resin hardener component includes an amine-based hardener, and may further include an inorganic and/or organic filler component. Cured reaction products of the composition demonstrate at about room temperature an adhesive strength of at least about 6500 psi, such as about 8000 to about 10000, and a fracture toughness of at least about 10 in-lbs/in2, such as about 20 to about 35 in-lbs/in2. In addition, the cured reaction products of the composition demonstrate a creep resistance at about room temperature at least about 6000 psi of at least about 1 hour.
    Type: Grant
    Filed: May 14, 1999
    Date of Patent: June 19, 2001
    Assignee: Loctite Corporation
    Inventor: Charles F. Schuft
  • Patent number: 6245828
    Abstract: The present invention is directed to polymerizable dental compositions containing a) 3 to 80 wt. % of cycloaliphatic epoxides; b) 0 to 80 wt. % of an epoxide or a mixture of epoxides which are different from a); c) 3 to 85 wt. % of a filer material; d) 0.01 to 25 wt. % of initiators, inhibitors and/or accelerators; e) 0 to 25 wt. % of auxiliary agents, the individual percentages of which are in relation to the total weight. The new polymerizable agents are particularly suited as dental material.
    Type: Grant
    Filed: September 21, 1998
    Date of Patent: June 12, 2001
    Assignee: ESPE Dental AG
    Inventors: Wolfgang Weinmann, Oswald Gasser, Rainer Guggenberger, Gunther Lechner, Wolfgang Soglowek, Joachim Zech
  • Patent number: 6221980
    Abstract: A latent curing agent is disclosed for epoxy resin, comprising a reaction product obtainable by allowing (A) an epoxy compound having more than one epoxy groups on the average in the molecule and (B) a compound having in the molecule both a tertiary amino group and at least one functional group selected from the group consisting of OH group, SH group, NH group, NH2 group, COOH group and CONHNH2 group, to react on each other in the presence of 0.05-5.0 equivalents of water per 1 equivalent of the epoxy group of Compound (A); and a curable epoxy resin composition comprising such curing agent and an epoxy compound having more than one epoxy group on the average in the molecule.
    Type: Grant
    Filed: April 16, 1999
    Date of Patent: April 24, 2001
    Assignee: Ajinomoto Co., Inc.
    Inventors: Junji Ohashi, Tetsuo Hinoma
  • Patent number: 6218483
    Abstract: Heat sensitive substrates, as well as others such as metal or glass, are electrostatically coated with a thermosetting coating powder comprising a melt-mixed, chilled, chipped, and powdered blend of an epoxy resin and a catalyst therefore, and a polyamine as a powdered low temperature curing agent along with a scavenger which will react secondarily with residual polyamine domains that do not contact the base epoxy resin during curing. The coating powder is deposited on the substrate and heated to fuse, flow and cure. The mixture of resin and catalyst does not cure within the extruder but it is made to cure at low temperatures on the desired substrate by the separate addition of the curing agent to the powdered melt-mixed blend.
    Type: Grant
    Filed: December 27, 1999
    Date of Patent: April 17, 2001
    Assignee: Rohm and Haas Company
    Inventors: Jeno Muthiah, Gordon Tullos, Jaquelyn Schelessman
  • Patent number: 6210811
    Abstract: An epoxy resin composition comprising an epoxy resin containing 0-10% by weight of a 2-nucleus compound and 50-100% by weight of 3 to 5-nucleus compounds combined and having a dispersity (Mw/Mn) of 1.0-1.7, an inorganic filler, a curing catalyst, and optionally a phenolic resin, and having a Tg of lower than 15° C. in an uncured state is effective in forming a flexible film which is easy to work at room temperature. A laminate film includes a layer of the epoxy resin composition and a protective layer. By sealing a semiconductor chip with the film, there is obtained a semiconductor package having improved heat resistance, improved moisture resistance, low stress property.
    Type: Grant
    Filed: September 24, 1999
    Date of Patent: April 3, 2001
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Tsuyoshi Honda, Miyuki Wakao, Hisashi Shimizu, Toshio Shiobara
  • Patent number: 6190834
    Abstract: The present invention provides a photosensitive resin composition capable of forming an insulating film, which is superior in both a roughening property and an adhesiveness, and a via-hole, which is highly reliable in connection, and a multilayer printed circuit board. The present invention provides a photosensitive resin composition containing a first resin, which is an epoxy resin, and a second resin having a N-substituted carbamic acid ester atomic group and a radical polymeric unsaturated bond in its side chain. The second resin is desirably an oligomer having a repeating unit expressed by the following general formula (chem. 1) or (chem. 3) by 3-10 units. Where, X is H or CH3, Y and Z is H or an alkyl group of carbon number 1-4, n is 0 or 1, a part of R1 is an atomic group expressed by the following general formula (chem. 2), the residual R1 is a hydroxyl group, and R2 is an alkylene group of carbon number 1-4.
    Type: Grant
    Filed: May 6, 1998
    Date of Patent: February 20, 2001
    Assignees: Hitachi, Ltd., Hitachi Chemical Company, Ltd.
    Inventors: Masatoshi Narahara, Mineo Kawamoto, Tokihito Suwa, Masao Suzuki, Satoru Amou, Akio Takahashi, Hiroyuki Fukai, Mitsuo Yokota, Shiro Kobayashi, Masashi Miyazaki
  • Patent number: 6165558
    Abstract: A moulding powder which is curable with the application of heat and pressure, comprising a mechanical mixture consisting of: a) a powdered epoxy compound containing on average more than one epoxy group in the molecule and having a softening point of above 60.degree. C., b) a powdered aliphatic or N-heterocyclic amine or a powdered amino group-containing adduct based on an aliphatic, cycloaliphatic, araliphatic or N-heterocyclic amine containing on average more than one amino group in the molecule and having a melting point or softening point of above 60.degree. C. and, optionally, c) customary additives for moulding powders, the particles of a) and b) being smaller than 200 .mu.m, is excellently suited for the preparation of coatings on heat-sensitive substrates and is used in particular in powder coating.
    Type: Grant
    Filed: July 16, 1998
    Date of Patent: December 26, 2000
    Assignee: Vantico, Inc.
    Inventor: Hildegard Schneider
  • Patent number: 6143809
    Abstract: A process to provide an aqueous dispersion is provided comprising the steps of:a) emulsifying a mixture comprisingi) water,ii) at least one epoxy resin having a functionality of greater than 0.8 epoxide group per molecule,iii) from 0.1 to 20 weight percent, based on the epoxy resin, of at least one polyoxyalkylene surfactant, andiv) optionally an acetone-free solvent solution to produce a resin-surfactant emulsion; andb) adding a solvent mixture to said resin-surfactant emulsion, said solvent mixture comprising i) acetone and ii) a non-volatile hydrophobic liquid resin or resin modifier to produce the aqueous dispersion.
    Type: Grant
    Filed: July 17, 1998
    Date of Patent: November 7, 2000
    Assignee: Shell Oil Company
    Inventors: Jimmy D. Elmore, Vincent James Maksymowski, Richard William Henning, Jr., Ernest Charles Galgoci, Jr.
  • Patent number: 6140430
    Abstract: Provided are low temperature curing thermosetting epoxy powder coating compositions comprising at least one non-crystalline epoxy resin, at least one crystalline epoxy resin, a curing agent, and a cure catalyst. Coatings made from such powder compositions exhibit a substantial reduction in bubble entrapment, enough to prevent a visible haze from forming in the coating, when cured at low temperatures demanded by brass substrates, while the powders from which the coatings are made still exhibit good storage stability and melt-processability.
    Type: Grant
    Filed: May 7, 1999
    Date of Patent: October 31, 2000
    Assignee: Morton International Inc.
    Inventors: William G. Ruth, Stacy L. Greth, Carryll A. Seelig, Dean A. Schreffler
  • Patent number: 6117953
    Abstract: A liquid epoxy resin composition comprising (A) an epoxy resin component which includes specific amounts of three specific epoxy resins, (B) a curing agent, (C) a curing accelerator, and (D) an inorganic filler has a low viscosity, high cure rate, ease of processing, reliability, and shelf stability. The composition can be used as a semiconductor device encapsulant to provide BGA packages having minimal warpage.
    Type: Grant
    Filed: January 21, 1999
    Date of Patent: September 12, 2000
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Nobuhiro Ichiroku, Toshio Shiobara
  • Patent number: 6100349
    Abstract: Proposed is a thermosetting powder coating composition comprising a mixture of particles reactive towards one another and a catalyst, with a portion of the reactive particles comprising a polymer reacting with epoxy to form ester forming or ether forming groups, while another portion comprises an at least bifunctional cross-linking agent which contains 2-oxo-1,3-dioxolan-4-yl groups, hereinafter referred to as cyclocarbonate groups, and, optionally, epoxy groups, with both the polymer reacting with epoxy to form ester forming and/or ether forming groups and the cross-linking agent being obtained by means of a non-vinylic addition and/or polymerization process. The catalyst used as ring opener for the cyclocarbonate groups is present in a quantity of 0.01 to 10, preferably 0.1 to 5, parts by weight per 100 parts by weight of the mixture of particles reactive towards one another. The quantity of epoxy oxygen present in the cross-linking agent after CO.sub.2 unblocking preferably is at least 0.4 wt. %.
    Type: Grant
    Filed: July 1, 1998
    Date of Patent: August 8, 2000
    Assignee: Akzo Nobel N.V.
    Inventors: Martinus Adrianus Anthonius Maria Koenraadt, Arie Noomen, Keimpe Jan Van Den Berg, Huig Klinkenberg, Klaus Hobel
  • Patent number: 6077929
    Abstract: The present invention pertains to coating compositions including a particular class of internally blocked polyamines as replacement for traditional blocked and unblocked polyamine crosslinkers. The use of these internally blocked polyamines results in better appearance characteristics and a lower VOC than are generally available with the traditional blocked varieties.
    Type: Grant
    Filed: April 7, 1998
    Date of Patent: June 20, 2000
    Assignee: Akzo Nobel N.V.
    Inventors: Johannes Adrianus Pardoen, Wincenty Lambertus Stanislaw Pilaszek, Jan Wilhelm Ernst Moos, Keimpe Jan Van Den Berg
  • Patent number: 6046284
    Abstract: A modified phenolic hydroxyl-containing resin having a low free difunctional phenol content and represented by general formula (1); a solid epoxy resin having an epoxy equivalent of 450 to 2,500 g/eq and prepared by epoxidizing the above resin; and another solid epoxy resin having an epoxy equivalent of 1,500 to 60,000 g/eq and a number-average molecular weight of 3,000 to 15,000 and prepared by reacting the above epoxy resin with a difunctional phenol compound. Resin compositions containing these resins have many applications as powder coatings and can paints. In formula (1), X represents a residue of a difunctional phenol compounds; X's may be the same or different; and n is the number of repeating units and is an integer of 0 or above.
    Type: Grant
    Filed: February 27, 1998
    Date of Patent: April 4, 2000
    Assignee: Tohto Kasei Co Ltd
    Inventors: Shuya Shinohara, Nobuhisa Saitoh, Yasuyuki Takeda, Masayoshi Hanafusa, Hidenori Nozawa
  • Patent number: 6040398
    Abstract: An epoxy curing agent comprising a heterocycle-containing compound having a backbone chain selected from the group consisting of polyether, polyvinyl, polyester, polyamide, polycarbonate, and novolac chains and at least two heterocyclic groups of the following general formula (1) as side chains, and a one-component (type) epoxy resin composition comprising said epoxy curing agent and a polyepoxy compound, ##STR1## wherein R.sub.1 and R.sup.2 may be the same or different and each represents hydrogen, straight-chain or branched C.sub.1 to C.sub.6 alkyl or alkenyl, or C.sub.6 to C.sub.8 aryl; or R.sub.1 and R.sup.2, taken together with the adjacent carbon atom, represents C.sub.5 to C.sub.7 cycloalkyl; R.sup.3 represents C.sub.1 to C.sub.10 alkylene. The object is to provide the one-component (type) epoxy resin composition having fast-curing feature, an improved storage stability, and an improved degree of workability.
    Type: Grant
    Filed: September 2, 1998
    Date of Patent: March 21, 2000
    Assignee: Sanyo Chemical Industries Ltd.
    Inventors: Toshihiko Kinsho, Munekazu Satake, Tadakazu Miyazaki
  • Patent number: 6040397
    Abstract: A single component, extremely low viscosity, pre-catalyzed high functionality diepoxide and epoxy resin system has been developed. This resin system has good thermal stability, an extended work life and is capable of being refrigerated to -18 C. and stored for extended periods of time with little or no change in physical or mechanical properties. The resin system has direct applications in a number of industries including, but not limited to, the aircraft and spacecraft industries. The resin system is a mixture of specific epoxy resins and curing agents that when combined form an extremely low viscosity resinous system that may be readily cured at a temperature as low as 52 degrees C. into novel thermoset materials prepared therefrom, which are characterized by superior strength properties and methods for preparing the same.
    Type: Grant
    Filed: July 6, 1998
    Date of Patent: March 21, 2000
    Assignee: Lockheed Martin Corporation
    Inventors: James R. Hooper, Richard K. Strother, John Fish, Paul G. Pawling, Gerald L. Sauer
  • Patent number: 6017634
    Abstract: A thermally curable adhesive composition that includes a fluxing agent that also acts as an adhesive is provided. The composition includes: (a) a fluxing agent represented by the formula RCOOH, wherein R comprises a moiety having two or more carbon-carbon double bonds wherein in one embodiment, at least one is within an acrylate or methacrylate group, and which may further contain at least one aromatic moiety; (b) a carboxylic acid neutralizing agent; (c) optionally, a crosslinkable diluent; (d) optionally, a source of free radical initiators; and (e) optionally, a resin. The composition can be applied directly onto the surface(s) of devices that are to be joined electrically and mechanically. These devices include, printed circuit substrates, connectors, components, cables, and other electrical devices having metallization patterns to be soldered together by means of a solder-bumped pattern on one or both surfaces.
    Type: Grant
    Filed: January 23, 1998
    Date of Patent: January 25, 2000
    Assignee: Miguel Albert Capote
    Inventors: M. Albert Capote, Liqui Zhou, Xioqui Zhu
  • Patent number: 5965269
    Abstract: An adhesive comprising (1) 100 parts by weight of a combination of an epoxy resin having a weight average molecular weight of less than 5,000 and a curing agent, (2) 10 to 40 parts by weight of a high-molecular weight component being compatible with the epoxy resin and having a weight average molecular weight of 30,000 or above, (3) 20 to 100 parts by weight of a high-molecular weight component being incompatible with the epoxy resin and having a weight average molecular weight of 30,000 or above, and (4) 0.1 to 5 parts by weight of a cure accelerator. The adhesive is excellent not only in moisture resistance, heat resistance, adhesive strength at high temperature, heat dissipation, reliability of insulation, crack resistance and flexibility but also in circuit filling and tight adhesion, and exhibits suitable flow properties.
    Type: Grant
    Filed: October 3, 1997
    Date of Patent: October 12, 1999
    Assignee: Hitachi Chemical Company, Ltd.
    Inventors: Teiichi Inada, Kazunori Yamamoto, Yasushi Shimada, Yasushi Kumashiro
  • Patent number: 5965673
    Abstract: A solid, one-component, flexible epoxy-based composition and method for making the same are provided. The present compositions comprise: (a) an epoxy-terminated prepolymer formed by reacting at least four moles of a polyepoxide resin with approximately one mole of a diamine compound, wherein at least one of the polyepoxide resin and diamine compound is solid at room temperature, and wherein the prepolymer is rheologically stable for weeks as a single component mixture at room temperature and, and (b) a substantially stoichiometric amount of an epoxy resin curing agent selected from the group consisting of a heat-curable, latent epoxy resin curing agent and a room temperature-curable ketimine curing agent. Optional components include thixotropic agents, diluents, fillers, anti-oxidants, and processing aids. The present uncured epoxy-based compositions upon cure, exhibit a durometer Shore D of less than about 45 (or a durometer Shore A of less than about 100).
    Type: Grant
    Filed: April 10, 1997
    Date of Patent: October 12, 1999
    Assignee: Raytheon Company
    Inventors: Ralph D. Hermansen, Steven E. Lau
  • Patent number: 5948881
    Abstract: Curative compositions of amine terminated polyamide resins blended with a deaminated bis-(p-aminocyclohexyl)methane composition (DeAms) are useful for curing adhesive epoxy resin compositions. The polyamides comprise combinations of fatty mono-acids, dimer acids, polyethyleneamines, and piperazine ring containing polyamines which are piperazine or N-aminoalkylpiperazine, where the alkyl chain is a C2 to C6 alkyl chain, wherein the ratio of equivalents of fatty mono-acid to dimer acid can range from about 0.001:1 to about 1:1, the ratio of moles of piperazine ring containing polyamine to polyethylene amine can range from about 0.1:1 to about 1:1, and the ratio of moles of polyamine to equivalents of acid can range from about 0.6:1 to about 1.2:1. DeAms is blended at 2 to 40 wt % based on polyamide. Adhesive compositions comprising these curatives are also disclosed.
    Type: Grant
    Filed: December 4, 1997
    Date of Patent: September 7, 1999
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Dilipkumar Nandlal Shah, William Edward Starner
  • Patent number: 5907020
    Abstract: Wood is electrostatically coated with a thermosetting powder coating system in which a mixture of a self-curing epoxy resin and a catalyst therefore is extruded and a low temperature curing agent are both pulverized and the powders are blended with conventional additives to make a coating powder which is deposited on a wooden substrate and heated to cure. The mixture of resin and catalyst does not cure within the extruder but it is made to cure at low temperatures by the separate addition of the curing agent. A small amount of the low temperature curing agent, insufficient to cause substantial curing during extrusion may be used in place of the catalyst.
    Type: Grant
    Filed: August 19, 1997
    Date of Patent: May 25, 1999
    Assignee: Morton International, Inc.
    Inventors: Glenn D. Correll, Andrew T. Daly, Joseph J. Kozlowski, Richard P. Haley, Jeno Muthiah, Paul R. Horinka, Eugene P. Reinheimer
  • Patent number: 5902643
    Abstract: Disclosed is a multilayer packaging material which is suitable for use as a container for malt beverages and which is tinted so as to block at least 90% of light with wavelengths of electromagnetic radiation ranging from 300 nm to 500 nm. The tinted multilayer packaging materials of the present invention includes: (a) at least one layer of a carbon dioxide (CO.sub.2)-permeable polymeric packaging material, and (b) at least one layer of a CO.sub.2 -treated gas barrier coating, which has an oxygen permeability constant not more than 0.05 cubic centimeter-mil/100 square inches/atmosphere/day. The CO.sub.2 -permeable packaging material can be any polymeric material through which CO.sub.2 can pass and which can be used as a packaging material for food or beverages. The gas barrier coating has an oxygen permeability constant, before CO.sub.2 treatment, of less than 0.3. This gas barrier coating includes the reaction product of a polyamine (A) and a polyepoxide (B).
    Type: Grant
    Filed: November 24, 1997
    Date of Patent: May 11, 1999
    Assignee: PPG Industries Inc.
    Inventors: Leland H. Carlblom, Jerome A. Seiner, Ken W. Niederst
  • Patent number: 5880228
    Abstract: Hardeners for epoxy resins include a reaction product of (A) a compound having an average of at least one 1,2-epoxide group per molecule, compound (A) being a reaction products of (A1) a polyfunctional epoxide having ate least two 1,2-epoxide groups per molecule of said epoxide and (A2) a monohydroxyaromatic compound, and (B) an amine. Epoxy resins cured with the hardeners are useful as coatings.
    Type: Grant
    Filed: July 31, 1997
    Date of Patent: March 9, 1999
    Assignee: Vianova Resins GmbH
    Inventor: Manfred Marten
  • Patent number: 5840825
    Abstract: Disclosed is a gas barrier coating and multilayer packaging materials made therefrom. The gas barrier coating includes a polyamine (A), a polyepoxide (B), and a filler (C). Polyamine (A) includes at least one of the following: (a) an initial polyamine, and (b) an ungelled polyamine adduct which is the reaction product of the initial polyamine and epichlorohydrin and/or a polyepoxide having a plurality of glycidyl groups linked to an aromatic member. Polyepoxide (B) includes a polyepoxide having a plurality of glycidyl groups linked to an aromatic member. Filler (C) includes a platelet-type filler with the following particle size distribution: (a) a number mean particle diameter in the range from about 5.5 to about 15 microns, and (b) a volume mean particle diameter in the range from about 8 to about 25 microns. In addition, the present invention provides glossy, multilayer packaging materials containing an oxygen barrier material layer having an oxygen permeability constant not more than 0.
    Type: Grant
    Filed: December 4, 1996
    Date of Patent: November 24, 1998
    Assignee: PPG Incustries, Inc.
    Inventors: Leland H. Carlblom, Jerome A. Seiner
  • Patent number: 5801218
    Abstract: The present invention provides a novel method for preparing a novel latent curing agent composition suitable for curing epoxy resin compositions. The present invention also provides the novel latent curing agent compositions.
    Type: Grant
    Filed: August 28, 1997
    Date of Patent: September 1, 1998
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Taun L. McKenzie, Allen L. Griggs
  • 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: 5798399
    Abstract: The present invention provides a novel method for preparing a novel curing agent composition suitable for curing epoxy resin compositions. The present invention also provides the novel curing agent compositions.
    Type: Grant
    Filed: August 28, 1997
    Date of Patent: August 25, 1998
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Allen L. Griggs, Taun L. McKenzie
  • Patent number: 5789498
    Abstract: A curing catalyst for use in epoxy resin, said curing catalyst being a metal salt complex of an adduct between polyepoxide and imidazoles; and a heat curing coating composition prepared by mixing the above curing catalyst with a coating composition containing an epoxy group-containing compound.
    Type: Grant
    Filed: December 5, 1996
    Date of Patent: August 4, 1998
    Assignee: Kansai Paint Co., Ltd.
    Inventors: Kazuhiko Ohnishi, Shigeo Nishiguchi
  • Patent number: 5773533
    Abstract: The invention relates to flame-resistant epoxy resin mixtures comprising epoxy resins, phosphorus-containing compounds and a hardener, which comprise a phosphorus-containing compound of the formula I or II ##STR1## in which R is a linear or branched alkyl, cycloalkyl, aryl or alkylaryl group having 1 to 18 carbon atoms or is hydrogen, and R' is a linear or branched alkylene, cycloalkylene, arylene or alkylarylene group having 1 to 18 carbon atoms, to a process for their preparation and to their use.
    Type: Grant
    Filed: March 27, 1997
    Date of Patent: June 30, 1998
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Sebastian Horold
  • Patent number: 5770658
    Abstract: Modified epoxy resins are obtained by reaction of an epoxy resin with up to one mol equivalent per epoxy group of an alkyl or alkenyl substituted, hydroxy substituted aromatic acid, especially by reaction of a bisphenol A epoxy resin with an alkylated salicylic acid. Also are described a process for the production of such modified resins, curable compositions comprising the modified epoxy resin and products provided with the cured composition, especially in coating applications and civil engineering applications.
    Type: Grant
    Filed: June 14, 1996
    Date of Patent: June 23, 1998
    Assignee: Shell Oil Company
    Inventors: Francoise Jacqueline Aline Baudoul, Seetha Maha Lakshmi Coleman-Kammula
  • 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: 5747565
    Abstract: A powder coating composition is disclosed which includes (a) 100 parts by weight of a mixed epoxy resin having an epoxy equivalent of 800-2000 and containing (a-1) a diglycidyl ether of bisphenol A having an epoxy equivalent of 180-2500 and (a-2) a rubber-modified epoxy resin having an epoxy equivalent of 180-2500 and obtained by reaction of a diglycidyl ether of bisphenol A with a carboxyl terminated acrylonitrile-butadiene copolymer; (b) a mixed curing agent consisting of (b-1) 0.05-5 parts by weight of an imidazole compound, (b-2) 0.5-10 parts by weight of dicyanodiamide and (b-3) 1-10 parts by weight of a dihydrazide of a dibasic carboxylic acid; and (c) 50-100 parts by weight of silica.
    Type: Grant
    Filed: March 1, 1993
    Date of Patent: May 5, 1998
    Assignee: Somar Corporation
    Inventors: Kazuya Ono, Akira Yasuda, Katsuji Kitagawa
  • Patent number: 5736620
    Abstract: Epoxy resins containing rodlike mesogenic moieties are prepared from phenolic hydroxyl containing compounds which contain such moieties.
    Type: Grant
    Filed: May 25, 1995
    Date of Patent: April 7, 1998
    Assignee: The Dow Chemical Company
    Inventors: Jimmy D. Earls, Robert E. Hefner, Jr., Paul M. Puckett
  • Patent number: 5733954
    Abstract: The present invention provides a novel method for preparing a novel latent curing agent composition suitable for curing epoxy resin compositions. The present invention also provides the novel latent curing agent compositions.
    Type: Grant
    Filed: December 14, 1995
    Date of Patent: March 31, 1998
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Taun L. McKenzie, Allen L. Griggs