Mixed With Nitrogen-containing Chemical Treating Agent Patents (Class 525/504)
  • Patent number: 6392003
    Abstract: The present invention provides a flame retardant phenol resin material which includes a phenol condensate, wherein a poly-aromatic compound obtained by a reaction of phenols (A) to aromatics (B) except for phenols and a heterocyclic compound (C) including nitrogen as heteroatom are condensed via aldehydes (D), and also provides a flame retardant epoxy resin material which includes an epoxy resin obtained by glycidyl-etherification of at least a part of phenolic hydroxyl groups of a poly-aromatic compound obtained by a reaction of phenols (A) to aromatics (B) except for phenols and a heterocyclic compound (C) including nitrogen as heteroatom are condensed via aldehydes (D).
    Type: Grant
    Filed: December 15, 1999
    Date of Patent: May 21, 2002
    Assignee: NEC Corporation
    Inventors: Yukihiro Kiuchi, Masatoshi Iji, Makoto Soyama
  • Patent number: 6365708
    Abstract: This invention relates to novel polyamines which are the reaction product of A) at least one nonaromatic diamine containing from 2 to 40 carbon atoms, wherein the amine groups are primary amine groups; and B) at least one epihalohydrin of the formula  where R is hydrogen or methyl and X is chlorine or bromine; and the coatings resulting from the reaction between the above reaction product and nonaromatic epoxy resins.
    Type: Grant
    Filed: December 20, 1999
    Date of Patent: April 2, 2002
    Assignee: Cognis Corporation
    Inventors: Shailesh Shah, Anbazhagan Natesh, Joseph Mulvey, Ronald C. LaFreeda, Gaetano D. DeAngelis, Ronald T. Cash, Jr.
  • Patent number: 6362359
    Abstract: The present invention relates to compounds containing modified hydrazide groups and corresponding to formula I wherein R represents the residue obtained by removing the isocyanate groups from a monomeric polyisocyanate, a polyisocyanate adduct or an NCO prepolymer, X represents OR′ or NHR′ and R′ represents a group which is inert to isocyanate groups under the conditions used to form the compound of formula I, R″ represents a divalent, linear or branched aliphatic group containing 2 to 10 carbon atoms, provided that there are at least two carbons between the oxygen atoms wherein the aliphatic group may optionally be substituted by heteroatoms to form ether or ester groups, and n is 2 to 6.
    Type: Grant
    Filed: December 1, 2000
    Date of Patent: March 26, 2002
    Assignee: Bayer Corporation
    Inventors: Sze-Ming Lee, Karen M. Henderson, Patricia B. Jacobs, Robert A. Sylvester, Douglas A. Wicks
  • Patent number: 6359036
    Abstract: A curing agent for epoxy resin which comprises at least one selected from 1-aminopyrrolidine and its salt.
    Type: Grant
    Filed: December 1, 1999
    Date of Patent: March 19, 2002
    Assignee: Otsuka Kagaku Kabushiki Kaisha
    Inventors: Yoshihisa Tomotaki, Takashi Kitajima, Keiichiro Ishikawa, Akihiro Nabeshima, Tomohiro Furuichi
  • 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: 6350818
    Abstract: The present invention relates to organic anti-reflective coating polymers and preparation methods therefor. Anti-reflective coatings are used in a semiconductor device during photolithography processes to prevent the reflection of light from lower layers of the device, or resulting from changes in the thickness of the photoresist layer, and to eliminate the standing wave effect when ArF light is used. The present invention also relates to anti-reflective compositions and coatings containing these organic anti-reflective coating polymers, alone or in combination with certain light-absorbing compounds, and preparation methods therefor.
    Type: Grant
    Filed: October 7, 1999
    Date of Patent: February 26, 2002
    Assignee: Hyundai Electronics Industries Co., Ltd.
    Inventors: Sung-Eun Hong, Min-Ho Jung, Hyeong-Soo Kim, Ki-Ho Baik
  • Patent number: 6303672
    Abstract: A self-dispersing curable epoxy composition is prepared upon contacting an epoxy resin with a polyoxyalkylenemonoamine having a molecular weight of from about 3,000 to about 15,000 in a ratio of about 0.001 to 0.060 reactive equivalents of polyoxyalkylenemonoamine to about 1.0 reactive equivalents of epoxy resin. 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: October 16, 2001
    Assignee: Henkel Corporation
    Inventors: John G. Papalos, Shailesh Shah, Reuben H. Grinstein, Joseph L. Mulvey, Brian G. Jewell
  • Patent number: 6294596
    Abstract: A self-dispersing curable epoxy composition is prepared upon contacting an epoxy resin with a polyoxyalkyleneamine having a molecular weight of from about 3,000 to about 15,000 in a ratio of about 0.001 to 0.060 reactive equivalents of polyoxyalkyleneamine to about 1.0 reactive equivalents of epoxy resin. 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 15, 1995
    Date of Patent: September 25, 2001
    Assignee: Henkel Corporation
    Inventors: John G. Papalos, Shailesh Shah, Reuben H. Grinstein, Joseph L. Mulvey, Brian G. Jewell
  • Patent number: 6288208
    Abstract: The present invention relates to a highly branched polyamide oligomer of the general formula (I) as hereinabove defined, to the process for preparing and branched oligomers and to different uses thereof. As well known to the man skilled in the art, the implementations and efficacy of the different polyamide oligomers may vary, depending on their structure and valency (reactive groups composition). Polyamide oligomers may be used, for example, as epoxy hardeners in the preparation of thermosetting compositions, as thermoplastic hot melt adhesives, as adhesion promoters and many other suitable applications. The highly branched oligomers disclosed have been shown to be highly efficient, for example, as epoxy hardeners, inter alia, in the formation of glue, lacquer, enamel or sealant mixtures.
    Type: Grant
    Filed: April 20, 1999
    Date of Patent: September 11, 2001
    Assignee: Epox, Ltd.
    Inventor: Leonid Moshinsky
  • Publication number: 20010018497
    Abstract: A polymer in the form of a novolac resin is provided wherein the novolac resin has a weight average molecular weight of 1,000-30,000, some of the hydrogen atoms of hydroxyl groups are replaced by 1,2-naphthoquinonediazidosulfonyl ester groups, and some of the hydrogen atoms of the remaining hydroxyl groups are replaced by substituted acetal groups and/or crosslinked within a molecule or between molecules with crosslinking groups having C—O—C linkages. The polymer is formulated into a positive resist composition having improved uniformity, sensitivity, resolution and pattern profile as well as improved heat resistance, film retention, substrate adhesion and storage stability.
    Type: Application
    Filed: February 7, 2001
    Publication date: August 30, 2001
    Inventors: Tomoyoshi Furihata, Hideto Kato, Yoshinori Hirano
  • Patent number: 6274682
    Abstract: An epoxy resin composition containing a) an epoxy resin and b) a liquid amine terminated polyamide curing agent prepared by condensing an aminoalkylpiperazine and a dicarboxylic acid. The epoxy resin composition typically requires less than 35% of solvent to produce a sprayable viscosity. The cured epoxy composition has good flexibility. A hydroxy-functional flexibilized resin is also produced by reacting (a) an epoxy resin, (b) a liquid aminoalkylpiperazine-based amine terminated polyamide and (c) a hydroxy-functional amine.
    Type: Grant
    Filed: January 25, 2000
    Date of Patent: August 14, 2001
    Inventors: Larry Steven Corley, Martin L. Ehrlich
  • Patent number: 6265491
    Abstract: A curable composition including a thermoset resin a curing agent component, an amount of a thermoplast component having reactive pendant and/or end groups, an organometallic curing catalyst component. The organometallic curing catalyst component is capable of forming cross-links with reactive pendant and/or end groups of the thermoset and thermoplast resins and comprises an organometallic complex compound of the formula I=M(R)n, where M is selected from titanium, zirconium, hafnium, cerium, vanadium, niobium, R is selected from mono-, bi- and tri and/or tetra dentate organic ligands and n is four or six.
    Type: Grant
    Filed: June 14, 1999
    Date of Patent: July 24, 2001
    Assignee: Cytec Technology Corp.
    Inventors: Jeffrey T. Carter, Patrick Terence McGrail
  • Patent number: 6245877
    Abstract: A moisture-cure urethane composition is disclosed. The urethane is formulated from an NCO-terminated alkoxylated phenolic resin that has long oxyalkylene chains. It has greater than 70 wt % solids and has excellent resistance to acids, bases, and chemicals.
    Type: Grant
    Filed: April 26, 2000
    Date of Patent: June 12, 2001
    Assignee: ARCO Chemical Technology, L.P.
    Inventors: Carmen L. Rodriguez, Stephen L. Goldstein
  • Patent number: 6231959
    Abstract: An epoxy resin composition featured in containing, in a matrix of an epoxy resin having more than two epoxy groups in each molecule, a phenolic hardening agent having more than two phenolic hydroxyl groups in each molecule, an organobis(N-dialkylurea) hardening promotion agent, a solvent for the hardening promotion agent, and a guanamine compound, and capable of obtaining a prepreg excellent in the preservation stability and, less causing a solvency errosion (halo phenomenon) due to an infiltration of plating solution along boundaries between a printed copper circuit formed in an inner-layered circuit board and a resin forming the prepreg, is realized.
    Type: Grant
    Filed: January 6, 1999
    Date of Patent: May 15, 2001
    Assignee: Matsushita Electric Works, Ltd.
    Inventors: Yoshihiko Nakamura, Masahiro Matsumura, Narimasa Iwamoto, Hidetsugu Motobe, Yukio Hatta
  • Patent number: 6150492
    Abstract: A two-part adhesive is provided wherein the first part comprises a stable aqueous alkaline monohydroxylic phenolic resole resin solution containing a methylene donor such as oxazolidine or a methylolurea and the second part comprises a stable resorcinolic resin precondensate having a shortage of formaldehyde and optionally containing a catalyst such as an ester functional compound for the resole resin. The resin in each part exhibits viscosity stability of an unmodified resin until mixed with the other part wherein the methylene donor, of the first part catalyzes the resorcinolic resin of the second part and the catalyst, when used, of the second part catalyzes the monohydroxylic phenolic resole resin of the first part. The adhesive finds utility in the production of structural lignocellulosic panels.
    Type: Grant
    Filed: February 4, 1994
    Date of Patent: November 21, 2000
    Assignee: Borden Chemical, Inc.
    Inventors: Earl K. Phillips, William D. Detlefsen, Fred E. Carlson
  • Patent number: 6150457
    Abstract: The present invention relates to compounds containing modified hydrazide groups and corresponding to formula I ##STR1## wherein R represents the residue obtained by removing the isocyanate groups from a monomeric polyisocyanate, a polyisocyanate adduct or an NCO prepolymer,X represents OR' or NHR' andR' represents a group which is inert to isocyanate groups under the conditions used to form the compound of formula I andn has a value of 2 to 6.The present invention also relates to one-component, thermoset coating compositions containing the compounds of formula I and a cross-linking component that is reactive with these compounds. Finally, the present invention relates coatings, sealants and adhesives prepared from these thermoset compositions.
    Type: Grant
    Filed: November 23, 1998
    Date of Patent: November 21, 2000
    Assignees: Bayer Corporation, Bayer Aktiengesellscaft
    Inventors: Sze-Ming Lee, Douglas A. Wicks, Eberhard Koenig, Carol L. Kinney, Karen M. Henderson
  • Patent number: 6136894
    Abstract: An aqueous epoxy resin system suitable for coatings comprises (a) water, (b) at least one epoxy resin and (c) a curing agent prepared by (i) reacting at least one polyamine having at least 3 active amine hydrogen atoms per molecule and at least one epoxy resin in an epoxy equivalent to to polyamine mole ratio of from 0.9:1 to 1:10 to obtain an amine-terminated intermediate; (ii) reacting the amine-terminated intermediate with from 0.5 to 25 weight percent, based on the amine-terminated intermediate, of an acid-terminated polyalkylene glycol to yield an amine-terminated curing agent. The amine-terminated intermediate can be capped with a monoepoxide in an amine hydrogen to epoxy groups ratio of from about 1.5:1 to 30:1 prior to reaction with the acid-terminated polyalkylene glycol, or the amine-terminated curing agent following step (ii) can be capped with a monoepoxide in an amine hydrogen atoms to epoxy groups ratio of from about 2:1 to 30:1.
    Type: Grant
    Filed: November 19, 1999
    Date of Patent: October 24, 2000
    Assignee: Shell Oil Company
    Inventors: Charles J. Stark, deceased, Gayle Edward Back, Jimmy D. Elmore, Kalyan Ghosh, Pen-Chung Wang, Kailash Dangayach
  • Patent number: 6133383
    Abstract: A method for preparing a high-heat-resistant-epoxy-resin composition which comprises adding, as catalytic curing agent, a quinoxalinium salt having a benzyl group to difunctional and multifunctional epoxy resin and thermoset resin having a similar structure. The epoxy-resin composition obtained by the present invention is excellent in its impregnating property, processability, impact resistance, drug resistance, electric-insulating property, and adhesiveness.
    Type: Grant
    Filed: October 28, 1997
    Date of Patent: October 17, 2000
    Assignee: Korea Research Institute of Chemical Technology
    Inventors: Jae-Rock Lee, Soo-Jin Park, Sang-Bong Lee
  • Patent number: 6127459
    Abstract: A water-compatible curing agent for epoxy resins is prepared by (a) reacting at least one polyamine having at least 3 active amine hydrogen atoms per molecule and at least one epoxy resin in an epoxy equivalent to polyamine mole ratio of from 0.9:1 to 1:10 to obtain an amine-terminated intermediate; (b) reacting the amine-terminated intermediate with from 0.5 to 25 weight percent, based on the amine-terminated intermediate, of an acid-terminated polyalkylene glycol to yield an amine-terminated curing agent. The amine-terminated intermediate can be capped with a monoepoxide in an amine hydrogen atoms to epoxy groups ratio of from about 1.5:1 to 30:1 prior to reaction with the acid-terminated polyalkylene glycol, or the amine-terminated curing agent produced following step (b) can be capped with a monoepoxide.
    Type: Grant
    Filed: June 10, 1998
    Date of Patent: October 3, 2000
    Assignee: Shell Oil Company
    Inventors: Charles J. Stark, deceased, Gayle Edward Back, Jimmy D. Elmore, Kalyan Ghosh, Pen-Chung Wang, Kailash Dangayach
  • Patent number: 6126932
    Abstract: This invention provides novel 5-HT.sub.1F agonists of Formula ##STR1## where X, R.sup.1, R.sup.2, and R.sup.3 are defined in the specification, which are useful for the treatment of migraine and associated disorders.
    Type: Grant
    Filed: October 12, 1999
    Date of Patent: October 3, 2000
    Assignee: Eli Lilly and Company
    Inventors: James E Fritz, Patric J Hahn, Stephen W Kaldor, Miles G Siegel, Yao-Chang Xu
  • Patent number: 6121405
    Abstract: A method for preparing a high-heat-resistant-epoxy-resin composition which comprises adding, as catalytic curing agent, a pyrazinium salt having a benzyl group to difunctional and multifunctional epoxy resin and thermoset resin having a similar structure. The epoxy-resin composition obtained by the present invention is excellent in its impregnating property, processability, impact resistance, drug resistance, electric-insulating property, and adhesiveness.
    Type: Grant
    Filed: October 29, 1997
    Date of Patent: September 19, 2000
    Assignee: Korea Research Institute of Chemical Technology
    Inventors: Jae-Rock Lee, Soon-Jin Park, Sang-Bong Lee, Kyu-Wan Lee
  • Patent number: 6114450
    Abstract: An adhesive for bonding a die of an integrated circuit chip comprises an aryl cyanate (ester) resin and/or a diepoxide resin admixed with tetrahydropyranyl-protected hydroxylmethylated phenolic resin or hydroxymethylated poly(hydroxystyrene) optionally further containing an electrically or thermally conductive filler.
    Type: Grant
    Filed: May 4, 1999
    Date of Patent: September 5, 2000
    Assignee: International Business Corporation
    Inventors: Krishna Gandhi Sachdev, Michael Berger, Anson Jay Call, Frank Louis Pompeo Jr.
  • Patent number: 6057389
    Abstract: The present invention provides pourable curable composition which comprises the product obtained by mixing (a) a liquid epoxy resin containing a sufficient amount of a thixotropic agent to induce thixotropic properties with (b) a hardener composition which contains a tertiary amine compound in an amount sufficient to at least cause the mixture to become pourable after mixing.
    Type: Grant
    Filed: February 12, 1998
    Date of Patent: May 2, 2000
    Assignee: Ciba Specialty Chemicals Corp.
    Inventors: Barry James Hayes, Kevin Brian Hatton, Jeffery Grant
  • Patent number: 6051632
    Abstract: Free-flowing compression molding compositions made up of from about 40 to about 80 wt. % of organic filler, from about 20 to about 60 wt. % of an organic reactive resin, and optionally further auxiliary substances and additives. The reactive resin contains an epoxide which may be liquid, a latent catalyst and a powdered polyisocyanate which is solid at room temperature.
    Type: Grant
    Filed: August 4, 1994
    Date of Patent: April 18, 2000
    Assignee: Bayer Aktiengesellschaft
    Inventors: Lutz Schrader, Hanns-Peter Muller, Richard Kopp
  • Patent number: 6046252
    Abstract: A binder composition of a phenolic novolac resin and a (lower) alkoxylated triazine-formaldehyde resin curing agent is disclosed. The triazine resins have sufficient carbon atoms in the alkoxy groups so as to provide a curing agent having a water solubility of less than 15%. The binder cures at high temperatures so as to provide improved flow and prolonged workability to the composition. The compositions are useful in refractory applications having a need for high temperature curing agents such as for maintenance and repair within refractory vessels by gunning/spraying, manufacture of electrodes by the Soderberg method, and for use in blast furnace tap holes.
    Type: Grant
    Filed: February 25, 1997
    Date of Patent: April 4, 2000
    Assignee: Borden Chemical, Inc.
    Inventor: Arthur H. Gerber
  • Patent number: 6040396
    Abstract: A formulation which contains:(1) the nucleophilic addition adduct of an imidazole and an unsaturated compound, which contains more than one imidazole moiety per molecule; and(2) an epoxy resin,is characterized in that fewer than 50 equivalent percent of the imidazole moieties in the adduct are neutralized with acid. The adduct may serve as a curing catalyst in high or low-temperature curing. The formulation is made and applied as a powder coating for coatings or as a matrix resin in laminates. It may be used in solvent-borne or liquid systems.
    Type: Grant
    Filed: July 22, 1997
    Date of Patent: March 21, 2000
    Assignee: The Dow Chemical Company
    Inventors: Joseph Gan, Gabriele Badini, Klaus E. Hoffmann
  • Patent number: 6001483
    Abstract: A composition useful as an encapsulating material for photosemiconductor elements such as a photodetector or light emmitor comprises an epoxy resin, a hardener and at least one compound represented by the following general formula (1) or (2):CH.sub.3 CH.sub.2 --(--CH.sub.2 --CH.sub.2 --).sub.x --CH.sub.2 --CH.sub.2 --O--(--CH.sub.2 --CH.sub.2 --O--).sub.n --Y.sub.1 (1)[CH.sub.3 CH.sub.2 --(--CH.sub.2 --CH.sub.2 --).sub.x --CH.sub.2 --CH.sub.2 --O--(--CH.sub.2 --CH.sub.2 --O--).sub.n --RCOO--].sub.m --Y.sub.2(2)wherein Y.sub.1 represents --H, --RCOOH, --COR' or --R'; R' is an alkyl group with not more than 30 carbon atoms; R is a divalent organic group; Y.sub.2 represents a metal atom having a valence of at least one; the mean value for x is from 8-200; and n is set such that the weight ratio of the repeating unit --CH.sub.2 --CH.sub.2 --O-- accounts for from 25-95% by weight based on the whole compound; and m is a positive integer corresponding to the valence of Y.sub.2.
    Type: Grant
    Filed: September 23, 1996
    Date of Patent: December 14, 1999
    Assignee: Nitto Denko Corporation
    Inventors: Tadaaki Harada, Shinjirou Uenishi, Hirokatsu Kouyama, Takahiko Maruhashi, Katsumi Shimada, Satoshi Tanigawa
  • Patent number: 5998575
    Abstract: A polymer alloy is obtained by adding a hydrophobic compound (1) having a hydrophobic main chain and a functional group containing an active hydrogen atom and a bisoxazoline compound (2) shown by the following formula to a composition containing plural polymers incompatible with each other: ##STR1## wherein D represents an optionally substituted alkylene group, cycloalkylene group or arylene group, R.sup.1, R.sup.2, R.sup.3 and R.sup.4 respectively represent a hydrogen atom or an optionally substituted alkyl group or aryl group. The compound (1) includes a compound having an aliphatic hydrocarbon group as a main chain, containing a carboxyl group and having a molecular weight of 10,000 or less (e.g. higher fatty acids). A compatibilizing agent as produced by reacting the compound (1) and an excess amount of the compound (2) can also be used.
    Type: Grant
    Filed: May 9, 1996
    Date of Patent: December 7, 1999
    Assignee: KRI International, Inc.
    Inventors: Hajime Kambara, Tak Yuen Chow
  • Patent number: 5981629
    Abstract: A two-component system for forming a sealing composition for bonding to unsanded, polymer-coated fiberglass surfaces. The system includes a resin component containing a major amount of epoxy resin, glycidoxy silane (0-2.5 wt. %) and hydrophilic-modified polyolefin fiber (0.5-10 wt. %), and a curing agent component having a major amount of amine curing agent and which may also contain amino silane (0-5 wt. %). The resin component may also contain alpha-phase alumina (20-80 wt. %), ceramic fiber (2-25 wt. %), and mica (2-20 wt. %). In another formulation, the resin component contains glycidoxy silane (0-2.5 wt. %), hydrophilic-modified polyolefin fiber (0.5-10 wt. %), ceramic fiber (2-25 wt. %), anti-foam material (0.2-1.0 wt. %), and epoxy novolac resin to 100 wt. %. The curing agent component contains amino silane (0-5 wt. %) and amine curing agent to 100 wt. %.
    Type: Grant
    Filed: November 24, 1997
    Date of Patent: November 9, 1999
    Inventor: Michael S. Cork
  • Patent number: 5977286
    Abstract: Epoxy resin compositions containing polyepoxides having at least two 1,2-epoxide groups are disclosed. The polyepoxides can be obtained by reacting (i) di- or polyepoxides or mixtures thereof with monoepoxides, (ii) one or more amines chosen from sterically hindered amines, disecondary diamines and diprimary diamines to form an epoxide-amine adduct, and (iii) subsequently reacting the epoxide-amine adduct with polyfunctional isocyanates. The composition also contains curing agents for the polyepoxides and can optionally contain additional 1,2-epoxide compounds and additives. The compositions are useful as coatings for bridging cracks, as adhesives and as constituents of paints.
    Type: Grant
    Filed: July 11, 1997
    Date of Patent: November 2, 1999
    Assignee: Vianova Resins GmbH
    Inventors: Manfred Marten, Claus Godau
  • Patent number: 5972423
    Abstract: A primerless method for repairing a substrate surface that includes applying to the surface a curable filler composition that includes (i) an epoxy compound, (ii) a polythiol curing agent, and (iii) a catalyst and then curing the composition. The filler composition can also include a polyamine in addition to the catalyst.
    Type: Grant
    Filed: August 3, 1998
    Date of Patent: October 26, 1999
    Assignee: Lord Corporation
    Inventors: Kirk J. Abbey, Mark W. Pressley, Ruth M. Bennett
  • 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: 5962602
    Abstract: An epoxy sealer/healer formulation for sealing and strengthening cracked concrete comprising an epoxy resin, an amine and a dialkylene triamine-alkylene oxide adduct, where the formulation provides a modulus and/or compressive strength at least that of uncracked concrete and effective for penetrating a concrete crack at a rate of at least 10 mm/min for a crack 0.5 mm wide when applied by gravity feed. The epoxy sealer/healer preferably has a viscosity of less than 100 centipoise and a tack-free time of less than 12 hours. The epoxy sealer/healer is advantageous in being able to bond to moist concrete surfaces. A method of using the epoxy sealer/healer for sealing and restoring the strength of cracked concrete is also set forth.
    Type: Grant
    Filed: February 29, 1996
    Date of Patent: October 5, 1999
    Assignee: Sika Corporation USA
    Inventors: Stuart J. Hartman, Michael C. Coddington, David C. Elmendorf, Norman Blank
  • Patent number: 5955543
    Abstract: An adhesive for bonding a die of an integrated circuit chip comprises an aryl cyanate (ester) resin alone and/or a diepoxide resin admixed with a hydroxymethylated phenolic resin or hydroxymethylated poly(hydroxystyrene) which can further contain an electrically or thermally conductive filler.
    Type: Grant
    Filed: May 21, 1997
    Date of Patent: September 21, 1999
    Assignee: International Business Machines Corporation
    Inventors: Krishna Gandhi Sachdev, Michael Berger, Anson Jay Call, Frank Louis Pompeo, Jr.
  • Patent number: 5955184
    Abstract: Disclosed in a halogen-free flame-retardant epoxy resin composition, comprising (A) a bisphenol A type epoxy resin, (B) a novolak type epoxy resin, (C) a phenolic resin type curing agent, (D) a curing accelerator, and (E) an inorganic filler. The phenolic resin type curing agent (C) is provided by a nitrogen-containing phenolic resin, preferably, by a co-condensation resin formed by the reaction among a phenolic compound, a guanamine compound, and an aldehyde compound. More desirably, a phenolic resin containing both phosphorus and nitrogen should be used as the curing agent (C). Further, a combination of the co-condensation resin noted above (C-1) and a reactive phosphoric acid ester can be used as a curing agent.
    Type: Grant
    Filed: May 28, 1997
    Date of Patent: September 21, 1999
    Assignee: Toshiba Chemical Corporation
    Inventors: Nobuyuki Honda, Tsuyoshi Sugiyama, Tetsuaki Suzuki
  • Patent number: 5952440
    Abstract: A curable, alkaline, melamine modified phenol-formaldehyde resin is prepared from an initial phenol-formaldehyde resole resin containing from 0.5 to 2.5 percent of free formaldehyde by scavenging formaldehyde with 1 to 12 parts of melamine for each 100 parts of the initial resin wherein the molar ratio of formaldehyde to melamine is 0.2 to 1.5 moles of formaldehyde for each mole of melamine to reduce the free formaldehyde to less than 70% of that in the initial resin and prepare a storage stable resin which contains less than 0.7% of free formaldehyde and which maintains its stability under application conditions. An ammonium salt of strong acid and additional water is incorporated in the melamine modified resin to prepare an alkaline binder. The binder is sprayed on to fiberglass with low formaldehyde emissions, good stability and rapid cure in the acid range.
    Type: Grant
    Filed: November 3, 1997
    Date of Patent: September 14, 1999
    Assignee: Borden Chemical, Inc.
    Inventors: Wayne R. Walisser, Calvin K. Johnson
  • Patent number: 5952447
    Abstract: Disclosed is a phenol resin composition containing a specific triazines-modified novolak phenol resin comprising phenols, triazines and aldehydes, and a method for producing the triazines-modified novolak phenol resin comprising the steps of as a first step reaction, successively effecting processes (i), (ii) and (iii), wherein said process (i) is a process for adjusting a pH of a system of a mixture of phenols, triazines and aldehydes in a range of 5 to 10, said process (ii) is a process for reacting said mixture under the condition that the aldehydes are not volatilized and said process (iii) is a process for removing a reaction water in the system; then as a second step reaction, successively effecting said processes (ii) and (iii) at a higher temperature than that of the first step reaction; thereafter as a third step reaction, successively effecting said processes (ii) and (iii) at a higher temperature than that of the second step reaction; and further, depending upon a necessity, repeating the second st
    Type: Grant
    Filed: May 8, 1998
    Date of Patent: September 14, 1999
    Assignee: Dainippon Ink and Chemicals, Inc.
    Inventor: Takashi Ikeda
  • Patent number: 5939508
    Abstract: A copolymer is formed from reacting, within a melt, a phthalonitrile resin with an epoxy resin having at least three epoxy groups. In an alternative embodiment, a copolymer is formed by reacting a phthalonitrile resin with an epoxy resin, at least one of the epoxy and phthalonitrile resins having a perfluorinated carbon. The copolymers of the present invention have exceptional thermal stability and a low affinity for water.
    Type: Grant
    Filed: March 31, 1997
    Date of Patent: August 17, 1999
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventor: Teddy M. Keller
  • Patent number: 5935710
    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: November 17, 1997
    Date of Patent: August 10, 1999
    Assignee: Vianova Resins GmbH
    Inventors: Michael Hoenel, Armin Pfeil, Thomas Budnick, Heiner Schwan
  • Patent number: 5936012
    Abstract: An electrodepositable composition that has: (A) an active hydrogen-containing cationic resin, electrodepositable on a cathode, having: (1) a polyepoxide; (2) an oxygen-substituted diamine compound having the following formula: ##STR1## where n is an integer from 2 to 4; and where R.sup.1 or R.sup.2 are the same or different and either one or both contain at least one oxygen and are alkyl, cycloalkyl, substituted alkyl, or substituted cycloalkyl having from 1 to 6 carbon atoms, or R.sup.1 and R.sup.2 are alkanol groups having from 2 to 6 carbon atoms, or R.sup.1, R.sup.2, and the N atom form a cyclic group which is substituted or unsubstituted such as morpholine and 1-(3-aminopropyl) imidazole; and (B) at least partially blocked isocyanate or polyisocyanate curing agent. The diamine compound of Formula I can be used alone or in conjunction with one or more secondary amines, nonhydroxy group containing amines and/or amines with ring structures.
    Type: Grant
    Filed: October 7, 1998
    Date of Patent: August 10, 1999
    Assignee: PPG Industries Ohio, Inc.
    Inventors: Marvin L. Kaufman, Patrick O'Neill, Richard F. Karabin, Gregory J. McCollum
  • Patent number: 5932682
    Abstract: A cleavable epoxy resin composition suitable for encapsulating electronic chips and a method for making the composition comprises the cured reaction product of a diepoxide; a cyclic dicarboxylic anhydride curing agent mixture; a 1,3-diaza compound having two nitrogen atoms present with one nitrogen atom doubly bonded to the central carbon and singly bonded to one other carbon, and the other nitrogen atom singly bonded to the central carbon and singly bonded to another carbon and singly bonded to a hydrogen. The 1,3-diaza compound serves either as the sole catalyst or in combination with a tertiary amine catalyst different from the diaza compound. The composition may include an optional hydroxy functional compound capable of reacting with the cyclic anhydrides to form a half ester thereby initiating the reaction between the diepoxide and the cyclic dicarboxylic anhydride curing agent. The resin can be used for the encapsulation of electronic parts, but can be removed by a solvent.
    Type: Grant
    Filed: December 19, 1995
    Date of Patent: August 3, 1999
    Assignee: International Business Machines Corporation
    Inventors: Stephen Leslie Buchwalter, Joseph Paul Kuczynski, John Gregory Stephanie
  • Patent number: 5922448
    Abstract: A curable resin blend including a multifunctional phenolic cyanate/phenolic triazine copolymer; and an epoxy resin, and articles manufactured therefrom. The cured resin blend possesses a high glass transition temperature, flexural strength, elongation, flexural modulus, compressive strength, and compressive modulus properties as well as low moisture absorption properties. The cured blend is suitable for making laminates, coatings, composites, and molds such as via resin transfer molding compression molding, and the like.
    Type: Grant
    Filed: May 19, 1995
    Date of Patent: July 13, 1999
    Assignee: AlliedSignal Inc.
    Inventors: Sajal Das, Geraldine Shu-Chuin Su
  • Patent number: 5912308
    Abstract: A curable resin blend including a multifunctional phenolic cyanate/phenolic triazine copolymer; and an epoxy resin, and articles manufactured therefrom. The cured resin blend possesses a high glass transition temperature, flexural strength, elongation, flexural modulus, compressive strength, and compressive modulus properties as well as low moisture absorption properties. The cured blend is suitable for making laminates, coatings, composites, and molds such as via resin transfer molding, compression molding, and the like.
    Type: Grant
    Filed: November 30, 1994
    Date of Patent: June 15, 1999
    Assignee: AlliedSignal Inc.
    Inventors: Sajal Das, Geraldine Shu-Chuin Su
  • Patent number: 5908901
    Abstract: An epoxy composition which is an infusible, gelled, heat curable, epoxy functional reaction product formed by mixing together:(A) one or more epoxy resins or epoxy group containing compounds;(B) a hardener system which will react with (A) to give a gelled solid, but which does not cause complete curing of (A) under the reaction conditions chosen for reaction of (A) and (B) to give a gelled solid; and(C) an optional further hardener system for (A) and the reaction product of (A) and(B), which is different from (B), and which remains largely unreacted with (A) and(B) under said reaction conditions.
    Type: Grant
    Filed: October 7, 1997
    Date of Patent: June 1, 1999
    Assignee: Ciba Specialty Chemicals Corporation
    Inventor: Peter Drummond Boys White
  • Patent number: 5908914
    Abstract: This invention relates to benzylic ether phenolic resole resins prepared in a sealed reaction vessel and their uses. The benzylic ether phenolic resole resins are prepared by heating phenol and an aldehyde in a sealed reaction vessel in the presence of a divalent metal catalyst without removing water generated by the reaction until an appropriate endpoint for the resin is reached. The benzylic ether phenolic resole resins produced by the process are preferably free or essentially free of unreacted formaldehyde and can be used in the resin component of phenolic-urethane foundry binders to make foundry cores and/or molds by the cold-box and no-bake processes. The cores and/or molds are used for making metal castings.
    Type: Grant
    Filed: July 17, 1996
    Date of Patent: June 1, 1999
    Assignee: Ashland Inc.
    Inventors: Thomas Edward Dando, William Rexford Dunnavant, Robert Bernard Fechter, Heimo Josef Langer
  • 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: 5889125
    Abstract: A curing component (A) containing amino groups available for reaction with epoxy resins (B), wherein the curing component (A) is a condensation product of di- or polyhydroxyaromatics (A1) with polyamines (A2) is disclosed. The curing component (A) is useful in preparing curing mixtures (C) which include the curing component (A) and at least one epoxy resin (B), whereby the curing mixtures are useful in the production of shaped articles and as coatings.
    Type: Grant
    Filed: August 13, 1997
    Date of Patent: March 30, 1999
    Assignee: Vianova Resins GmbH
    Inventors: Uwe Neumann, Claus Godau
  • Patent number: 5888655
    Abstract: A composite coating is described. The composite comprises a substrate; one or more primer coating layers disposed on the substrate; and at least one topcoat layer disposed on the outermost primer coating layer. The outermost primer coating layer is obtained by reaction of a primer composition that includes a novolac resin having at least one carbamate group and an aminoplast resin.
    Type: Grant
    Filed: June 30, 1997
    Date of Patent: March 30, 1999
    Assignee: BASF Corporation
    Inventors: Paul J. Harris, Gregory G. Menovcik
  • Patent number: 5876210
    Abstract: The invention concerns a process for preparing a polymer composition, that is free-radical/photochemical and thermal curing epoxide-methacrylate and/or isocyanate-methacrylate adhesives in broadest terms, dental/medical adhesives, and dental restoratives. Furthermore the dual curing epoxide-methacrylate and/or isocyanate-methacrylate adhesives can be used in the optical industry, in optoelectronics and microelectronics, for example for the adhesion of complicated optical components in the combination glass/glass, glass/metal. Advantageous is the small shrinkage during polymerization and the good mechanical properties in combination with the possibility of step-wise or one-step polymerization.
    Type: Grant
    Filed: November 21, 1996
    Date of Patent: March 2, 1999
    Assignee: Dentsply G.m.b.H.
    Inventors: Joachim E. Klee, Walter Leube
  • 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