Nitrogen Material Contains A Nitrogen Atom As Part Of A Heterocyclic Ring Patents (Class 528/94)
  • Patent number: 6225378
    Abstract: A triazine compound having formula I or formula II: Wherein n is integer from 1 to 5; R1 is hydrogen, halogen, C1-C4 alkyl, or C1-C4 alkoxyl; and R2 is aliphatic amine, aliphatic alcohol, alicyclic amine or alicyclic alcohol, and an epoxy resin composition containing the triazine compound. The epoxy resin composition is suitable for the preparation of the structural substrate of printed circuit boards having low dielectric constant.
    Type: Grant
    Filed: July 1, 1999
    Date of Patent: May 1, 2001
    Assignee: Industrial Technology Research Institute
    Inventors: Shin-Shin Wang, Hung-Chou Kang, Jie-Hwa Ma, Meng-Song Yin, Se-Tsun Hong, Kuo-Yuan Hsu, Kung-Lung Cheng
  • Patent number: 6207786
    Abstract: Low viscosity ternary mixtures of benzoxazine, epoxy and phenolic resins have been developed. The blends render homogeneous and void free cured specimen with a wide range of properties. Melt viscosity values as low as 0.3 Pa.s at 100° C. can be achieved. The phenolic resin acts as a cure accelerator to the system, besides its typical function as a hardener of epoxy resin. Glass transition temperatures Tg as high as 170° C. can also be obtained.
    Type: Grant
    Filed: November 10, 1998
    Date of Patent: March 27, 2001
    Assignee: Edison Polymer Innovation Corporation
    Inventors: Hatsuo Ishida, Sarawut Rimdusit
  • Patent number: 6194490
    Abstract: A composition, which comprises (a) a compound containing at least one epoxy group in inner position per molecule, obtained by epoxidation of a natural unsaturated oil or of its derivative; (b) an epoxy compound selected from the group consisting of glycidyl ethers, glycidyl esters and cycloaliphatic epoxides; (c) a polycarboxylic acid anhydride; (d) a compound of formula I, I, III or IV or an acid adduct of a compound of formula I, II, III or IV  wherein R1 to R4 are each independently of one another hydrogen; C1-C18alkyl which is unsubstituted or substituted by one or more than one hydroxyl group amino group, halogen atom, cyano group, C1-C6alkoxy group or C1-C6cyanalkoxy group; C5-C14aryl, C6-C24aralkyl, C3-C14heteroaryl or C4-C14heteroaralkyl which are unsubstituted or substituted by one or more than one C1-C6alkyl group, C1-C6alkoxy group or halogen atom,  n is an integer from 1 to 3, and  R5 and R6 are each independently of the other C1-C6alkyl or, together with the
    Type: Grant
    Filed: February 19, 1999
    Date of Patent: February 27, 2001
    Assignee: Vantico, Inc.
    Inventors: Martin Roth, Qian Tang, Roger Malherbe, Catherine Schoenenberger
  • 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: 6124381
    Abstract: An epoxy/acid anhydride composition characterized by containing, as a curing accelerator, a substituted triazine of the formula [I] ##STR1## (wherein X is an amino group, C.sub.1-18 monoalkylamino group, di C.sub.1-18 alkylamino group, morpholino group, piperidino group, methyl group or phenyl group; R.sup.1 and R.sup.2 independently each represent C.sub.1-12 alkyl group, C.sub.1-12 hydroxyalkyl group, C.sub.4-8 cycloalkyl group, C.sub.5-9 cycloalkylmethyl group or C.sub.5-9 methylcycloalkyl group) in an epoxy/acid anhydride composition in which an epoxy compound and an acid anhydride-curing agent are contained, and an epoxy/acid anhydride resin composition prepared by thermosetting the epoxy/acid anhydride composition.
    Type: Grant
    Filed: December 15, 1997
    Date of Patent: September 26, 2000
    Assignee: Nissan Chemical Industries, Ltd.
    Inventors: Satoru Miyake, Kenichi Osawa, Toshinari Koda, Motohiko Hidaka
  • 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: 6110993
    Abstract: The present invention provides a thermosetting epoxy resin composition which copes with both storage stability and curing properties at a low temperature. A thermosetting epoxy resin composition of the present invention comprises (A) an epoxy resin, and (B) a fine powder-treated curing agent which comprises a curing agent in the solid state at room temperature, and particle surfaces of which are adhered with a fine powder having a center particle size of 2 .mu.m or less in a weight ratio of said solid curing agent to said fine powder in the range between 1:0.001 to 1:0.7, for hiding active sites on the surface of the curing agent. This composition is useful as an adhesive, a sealant, a coating material, a paint, a potting material, and a molding material.
    Type: Grant
    Filed: March 27, 1998
    Date of Patent: August 29, 2000
    Assignee: Sunstar Giken Kabushiki Kaisha
    Inventors: Atsushi Saito, Tatsuya Okuno
  • Patent number: 6107437
    Abstract: Curing agents for epoxy resins are provided in which an imidazole is substituted on the nitrogen atom by a long chain group. This provides greater latexing (stability) at ambient temperatures without adversely affecting curing properties at temperatures of 50.degree. C. upwards. Those components in which the chain is substituted by a hydroxy group on the 2 position are particularly preferred and are novel compounds.
    Type: Grant
    Filed: September 28, 1998
    Date of Patent: August 22, 2000
    Assignee: Hexcel Corporatioin
    Inventors: John Leslie Cawse, Mark Whiter
  • Patent number: 6103853
    Abstract: Amine adducts comprising a reactive amine curing agent containing an aromatic silane epoxy along with improved coatings made by combining the amine adduct with additional epoxy material. The amine adducts, when formulated and cured with an epoxy material, cures in several hours and gives a protective coating material that cures without blush or CO.sub.2 incorporation. Specific embodiments of the amine adduct contain a bisepoxy compound, such as 2,11-bis(3-glycidylphenyl)-2,11dimethyl-2,11-disiladodocane (n=4), for example, while the amine functionalized compound may be ethylenediamine (90.degree. C., 120.2 g, 20 mol) or aminoethylpiperazine, respectively. A number of chemical compounds are also disclosed.
    Type: Grant
    Filed: January 29, 1998
    Date of Patent: August 15, 2000
    Assignee: Raytheon Company
    Inventors: T. Kirk Dougherty, Steven E. Lau, Teresa L. Rosales, Steven A. Tunick
  • Patent number: 6096808
    Abstract: A two-stage accelerator for use in filled anhydride/epoxy systems is disclosed. In particular, the present invention makes use of a first accelerator to initiate curing of the epoxy while the filler becomes wetted, and a second, faster accelerator to complete the curing process.
    Type: Grant
    Filed: January 29, 1998
    Date of Patent: August 1, 2000
    Assignee: Alpha Metals, Inc..
    Inventor: Ken Gilleo
  • Patent number: 6084037
    Abstract: In an epoxy resin composition comprising an epoxy resin, a curing agent, and an inorganic filler, there are blended a salt of trimellitic anhydride with 1,8-diazabicyclo(5.4.0)undecene-7 as a curing accelerator and a mercapto-containing silane coupling agent. The composition is shelf stable and smoothly flowing and cures into a product having improved adhesion, moisture resistance and electrical properties. The composition is suitable for the encapsulation of semiconductor devices.
    Type: Grant
    Filed: December 18, 1997
    Date of Patent: July 4, 2000
    Assignee: Shin -Etsu Chemical Co., Ltd.
    Inventors: Hisashi Shimizu, Minoru Takei, Masachika Yoshino, Toshio Shiobara
  • Patent number: 6077886
    Abstract: A curable epoxy resin composition comprising (A) an epoxy resin, (B) a thixotropic agent in an amount sufficient to induce thixotropic properties, and a hardener comprising (C) at least one polyethyleneimine and (D) at least one other amine having at least 2 amino hydrogen atoms, the combined amounts of (C) and (D) being sufficient to effect cure of the epoxy resin.
    Type: Grant
    Filed: October 9, 1997
    Date of Patent: June 20, 2000
    Assignee: Ciba Specialty Chemicals Corpation
    Inventors: Barry James Hayes, Kevin Brian Hatton
  • 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: 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: 6034200
    Abstract: A heat-curable resin composition comprising a multifunctional epoxy resin monomer and a heat-latent curing agent of formula (I) provides a cured epoxy resin having good thermal and dimensional stability: ##STR1## wherein: R is hydrogen, a C.sub.1-4 alkyl or C.sub.1-4 alkoxy group.
    Type: Grant
    Filed: March 17, 1998
    Date of Patent: March 7, 2000
    Assignee: Korea Research Institute of Chemical Tech.
    Inventors: Jae-Rock Lee, Soo-Jin Park, Sang-Bong Lee
  • Patent number: 6011130
    Abstract: Provided is an epoxy resin composition comprising a crystalline epoxy resin and an amorphous epoxy curing agent, wherein the crystalline epoxy resin is dispersing uniformly in the amorphous epoxy curing agent as crystallites. The epoxy resin composition is excellent in preservation stability.
    Type: Grant
    Filed: September 12, 1997
    Date of Patent: January 4, 2000
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Noriyuki Arai, Masatsugu Akiba
  • Patent number: 6008313
    Abstract: Compositions of amine terminated polyamide resins useful for curing epoxy resins are disclosed comprising combinations of fatty mono-acids, dimer acids, polyethyleneamines, and piperazine ring containing polyamines having an N--H functionality of 2 or 3 per mole selected from the group consisting of 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. Coating compositions comprising these polyamide resins are also disclosed.
    Type: Grant
    Filed: November 19, 1997
    Date of Patent: December 28, 1999
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Frederick Herbert Walker, William Edward Starner, Andrea Karen Smith
  • Patent number: 5955551
    Abstract: The present invention relates to polyglycidyl ether compounds containing at least three mono- or divalent radicals A of the general formula wherein R.sub.
    Type: Grant
    Filed: August 6, 1997
    Date of Patent: September 21, 1999
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Chi-Wen Frank Cheng, Mark Bryant
  • Patent number: 5952446
    Abstract: An elastomeric epoxy composition and curing agents for elastomeric epoxy compositions, the elastomeric epoxy composition being the reaction product of a substituted amide and an epoxy.
    Type: Grant
    Filed: February 9, 1998
    Date of Patent: September 14, 1999
    Assignee: Molex Incorporated
    Inventor: Paul Krebaum
  • Patent number: 5948923
    Abstract: A number of new phenolepoxy resins are prepared by reacting polyphenol, epihalohydrin and imidazole in a homogeneous reaction medium.
    Type: Grant
    Filed: October 30, 1998
    Date of Patent: September 7, 1999
    Assignee: Industrial Technology Research Institute
    Inventors: Kung-Lung Cheng, Woan-Shiow Tzeng, Shu-Chen Lin
  • 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: 5912316
    Abstract: A resin composition, for use as a die attach adhesive, heat sink attach adhesive, encapsulant or underfill, comprises a resin system, including a mixture of an epoxy resin and a cyanate ester resin, and a polyamide catalyst. The composition is curable in one minute at 200.degree. C. and has a pot life of at least 18 hours at room temperature. The resin composition is flexible, develops high adhesion, high moisture resistance, low weight loss during curing and requires no solvents.
    Type: Grant
    Filed: May 19, 1997
    Date of Patent: June 15, 1999
    Assignee: Johnson Matthey, Inc.
    Inventors: Guy P. Nguyen, Carl Edwards
  • Patent number: 5912317
    Abstract: An improved oxazolidine-based hardener to be used with a resorcinol resin or a tannin resin as the adhesive for the bonding of wood articles. Preferably, an oxazolidine is combined with particulate silica, and the resin is combined with a base such as NaOH. The adhesive based on the improved hardener can be used to glue wood particles to pass wet strength requirements after the glue is cured at room temperature for under 24 hours. The improved hardener composition is storage stable; it can be prepared anytime before its use and, thus, eliminate the need to prepare a hardener immediately prior to the glue use. Since it is formaldehyde-free; it eliminates the safety issues associated with handling formaldehyde or paraformaldehyde. Also, the hardener provides flexible gel time or working time. Since the resins can be cured at room temperature, heating in an oven is not needed but could be used to reduce curing time. If radio frequencies are used to cure the resins, the exposure time can be reduced.
    Type: Grant
    Filed: August 15, 1997
    Date of Patent: June 15, 1999
    Assignee: ANGUS Chemical Company
    Inventor: Gaoming Wu
  • Patent number: 5904888
    Abstract: A two-component system for producing two or more different curable mixtures in which the first component A is common to each mixture and comprises:1. a liquid epoxy2. an acid anhydride hardener and3. at least one fillerand the second component B is selected from two or more different components B, each of which comprises:1. an accelerator, and optionally2. a colourant, and optionally3. a non-volatile solvent/extender for the accelerator4. a flexibiliser for the epoxy-anhydride cure5. a acid anhydride hardener.
    Type: Grant
    Filed: December 18, 1997
    Date of Patent: May 18, 1999
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Barry James Hayes, Paul Terrence Wombwell, Philip David Willis
  • Patent number: 5874501
    Abstract: The present invention relates to a novel oxirane pre-polymer comprised of the catalyzed or uncatalyzed reaction product of phenyl intermediates with a difunctional oxirane oligomer having at least one aromatic moiety and at least one aliphatic moiety, characterized in that substantially hydrolyzable oxygen atoms in said phenyl are bonded to said oligomers, and there is substantially no bonding between oligomer moieties. In a particularly preferred embodiment the present invention relates to a novel oxirane prepolymer comprising the reaction product of a phenyl intermediate with an inorganic oxide having at least one hydrolyzable oxygen and a difunctional oxirane oligomer aliphatic moiety characterized in that a majority of all hydrolyzable oxygen atoms in said oxide are bonded to at least one of the phenyl groups of the intermediate phenyl and one phenyl group is bonded to said oligomer and there is substantially no bonding between oligomer moieties.
    Type: Grant
    Filed: August 18, 1997
    Date of Patent: February 23, 1999
    Inventor: Donald J. Keehan
  • Patent number: 5844062
    Abstract: A process for preparing phenolepoxy resin represented by the following formula: ##STR1## wherein: (a) R.sup.1, R.sup.2, R.sup.3, and R.sup.4, which can be the same or different, are hydrogen, C.sub.1 to C.sub.6 alkyl groups, C.sub.6 to C.sub.10 aromatic groups, or C.sub.1 to C.sub.6 alkyl group-substituted C.sub.6 to C.sub.10 aromatic groups; (b) R.sup.5 and R.sup.6, which can be the same or different, are hydrogen, C.sub.1 to C.sub.6 alkyl groups, C.sub.6 to C.sub.10 aromatic groups, or C.sub.1 to C.sub.6 alkyl group-substituted C.sub.6 to C.sub.10 aromatic groups; ##STR2## (c) R.sup.7 is hydrogen, C.sub.1 to C.sub.6 alkyl groups, C.sub.6 to C.sub.10 aromatic groups, or C.sub.1 to C.sub.6 alkyl group-substituted C.sub.6 to C.sub.10 aromatic groups; (d) R.sup.8 and R.sup.9, which can be the same of different, are hydrogen, C.sub.1 to C.sub.6 alkyl groups, C.sub.6 to C.sub.10 aromatic groups, or C.sub.1 to C.sub.6 alkyl group-substituted C.sub.6 to C.sub.10 aromatic groups; and (e) n is an integer of 0 or 1.
    Type: Grant
    Filed: April 29, 1997
    Date of Patent: December 1, 1998
    Assignee: Industrial Technology Research Institute
    Inventors: Kung-Lung Cheng, Woan-Shiow Tzeng, Shu-Chen Lin
  • Patent number: 5821317
    Abstract: The invention pertains to an adduct obtainable by condensation of a bisepoxy compound and a P-guanamine according to the formula ##STR1## wherein X is CR.sub.3 R.sub.4 --(CR.sub.1 R.sub.2).sub.n --CR.sub.5 R.sub.6 or o-phenylidene, n is 0 or 1, and R.sub.1 -R.sub.8 may be the same or different and represent H, methyl or ethyl, and the molar ratio P-guanamine: bisepoxide is 0.60 to 0.35. The adduct is used in the manufacture of synthetic materials, notably printed wiring boards (PWBs).
    Type: Grant
    Filed: August 13, 1997
    Date of Patent: October 13, 1998
    Assignee: Akzo Nobel NV
    Inventors: Antonius Johannes Wilhelmus Buser, Jan Andre Jozef Schutyser
  • Patent number: 5817736
    Abstract: Epoxy resin mixtures to produce prepregs and composites contain the following components:a phosphorus-modified epoxy resin with an epoxy value of 0.02 to 1 mol/100 g, made up of structural units derived from(a) polyepoxy compounds with at least two epoxy groups per molecule and(b) phosphinic acid anhydrides, phosphonic acid anhydrides or phosphonic acid half-esters;dicyandiamide and/or an aminobenzoic acid derivative as the hardener;an amino hardening accelerator.
    Type: Grant
    Filed: March 10, 1997
    Date of Patent: October 6, 1998
    Assignee: Siemens Aktiengesellschaft
    Inventors: Wolfgang von Gentzkow, Jurgen Huber
  • 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: 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: 5721323
    Abstract: A class of compounds which inhibits the reaction of a polyepoxide with a curing agent at low temperatures including an epoxy resin composition containinga) a polyepoxide;b) an amine or amide curing agent for the polyepoxide;c) at least about 15 meq (per equivalent of polyepoxide) of a catalyst for the reaction of the polyepoxide with the curing agent; andd) a cure inhibitor selected such that:(1) at about 171.degree. C. the composition has a gel time that is at least about 50 percent longer than a similar composition without the inhibitor, and(2) at about 175.degree. C. and higher the composition cures in no more than about 50 minutessuch that the composition cures rapidly with high cross-link density because it has a high catalyst loading, while the inhibitor lengthens the gel time to permit laminating and other processing.
    Type: Grant
    Filed: December 27, 1996
    Date of Patent: February 24, 1998
    Assignee: The Dow Chemical Company
    Inventors: Craig E. Schultz, James L. Bertram, William A. Clay, Guang-Ming Xia, Joseph Gan
  • Patent number: 5717011
    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: December 14, 1995
    Date of Patent: February 10, 1998
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Allen L. Griggs, Taun L. McKenzie
  • Patent number: 5688877
    Abstract: A method of preparing epoxy parts wherein the interval of low viscosity of an amine-hardened epoxy system can be extended without sacrifice of cure time. Suitable catalysts for the epoxy-amine hardener reaction are generated in situ. As an advantage, more epoxy articles may be prepared with a given mold capacity having improved wet-out of fiber reinforcement attributed to a larger interval of low viscosity.
    Type: Grant
    Filed: June 11, 1996
    Date of Patent: November 18, 1997
    Assignee: The Dow Chemical Company
    Inventors: Raymond A. Koenig, Joseph Gan, Richard J. Hayman
  • Patent number: 5686185
    Abstract: A thermosetting epoxy resin powder coating composition is provided that comprises an epoxy resin composed of a diglycidyl ether of bisphenol A, a curing agent composed of a bisphenol A encapped diglycidyl ether of bisphenol A, and a cure catalyst composed of an imidazole adducted to a diglycidyl ether of bisphenol A, in which the ratio of curing agent to epoxy resin is below 70% stoichiometry, and preferably between about 10% and 60% stoichiometry. The thermosetting epoxy resin powder coating composition not only exhibits the desired flexibility and fast cure speeds, but also exhibits superior adhesion and superior resistance to delamination and cathodic disbondment, preferably having cathodic disbondment values typically less than 4 mm radial disbondment, and preferably less than 2 mm radial disbondment. Such properties are highly advantageous for protective powder coatings used on rebars and pipelines.
    Type: Grant
    Filed: December 30, 1996
    Date of Patent: November 11, 1997
    Assignee: Morton International, Inc.
    Inventors: Glenn D. Correll, Roy M. Berstler
  • Patent number: 5672431
    Abstract: The present invention provides a curable epoxy resin composition, which includes an epoxy resin; from 10 to 60 percent by weight of the epoxy resin of an amine curing agent; from 0.1 to 5 percent by weight of the epoxy resin of an imidazole accelerator; and from 0.01 to 5 percent by mole of the epoxy resin of chromium acetylacetonate (Cr(acac).sub.3). The resultant cured epoxy resin prepared from the epoxy resin composition of the present invention demonstrates improved fracture toughness. Also, the interlaminar fracture energy of the resultant graphite/epoxy laminate prepared from the cured epoxy resin of the present invention is greater than that of the conventional graphite/epoxy laminate.
    Type: Grant
    Filed: February 21, 1996
    Date of Patent: September 30, 1997
    Assignee: National Science Council
    Inventor: King-Fu Lin
  • Patent number: 5658996
    Abstract: The present invention relates to a novel oxirane pre-polymer comprised of the catalyzed or uncatalyzed reaction product of tris or tetraphenyl intermediates with a difunctional oxirane oligomer having at least one aromatic moiety and at least one aliphatic moiety, characterized in that substantially hydrolyzable oxygen atoms in said phenyl are bonded to said oligomers, and there is substantially no bonding between oligomer moieties. In a particularly preferred embodiment the present invention relates to a novel oxirane prepolymer comprising the reaction product of a phenyl intermediate with an inorganic oxide having at least one hydrolyzable oxygen and a difunctional oxirane oligomer aliphatic moiety characterized in that a majority of all hydrolyzable oxygen atoms in said oxide are bonded to at least one of the phenyl groups of the tris-phenyl and one phenyl group of the tris-phenyl group is bonded to said oligomer and there is substantially no bonding between oligomer moieties.
    Type: Grant
    Filed: February 20, 1996
    Date of Patent: August 19, 1997
    Inventor: Donald J. Keehan
  • 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: 5623023
    Abstract: Disclosed is a curable composition comprising (A) an imidazole derivative represented by the following general formula (1), which is capable of generating free imidazole by exposure to light, and (B) a polyfunctional epoxy compound: ##STR1## wherein R represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, an aralkyl group, a nitro group, a cyano group, an alkoxyl group, a phenoxy group, or an aromatic ring residue capable of forming a condensed ring in combination with a benzene ring. The composition may further incorporate therein at least one compound selected from the group consisting of polyfunctional phenol compounds, polyfunctional carboxylic acids, acid anhydrides, and amine compounds.
    Type: Grant
    Filed: May 21, 1996
    Date of Patent: April 22, 1997
    Assignee: Taiyo Ink Manufacuturing Co., Ltd.
    Inventor: Tadatomi Nishikubo
  • Patent number: 5620831
    Abstract: Disclosed are novel cyanoguanidine derivatives which are usable as an epoxy resin curing agent and are represented by the following general formula (1). A thermosetting resin composition and a photocurable and thermosetting resin composition containing the following cyanoguanidine derivatives and other derivatives as the epoxy resin curing agent are also disclosed. ##STR1## wherein R.sup.1 represents a substituent selected from the group consisting of the following substituents (a) through (k).
    Type: Grant
    Filed: March 28, 1995
    Date of Patent: April 15, 1997
    Assignee: Taiyo Ink Manufacturing Co., Ltd.
    Inventor: Osamu Kawana
  • Patent number: 5616658
    Abstract: A curing agent for a composition useful for the production of matt epoxy resin and hybrid powder coatings, comprising a mixture ofa) salts of phthalic acid, isophthalic acid and terephthalic acid with the following amines ##STR1## in which R.sub.1, R.sub.2 and R.sub.3 are identical or different aliphatic, cycloaliphatic, araliphatic or aromatic hydrocarbon radicals having 1-20 carbon atoms and in which one or more CH.sub.2 groups in the carbon chain may be replaced by 0 atoms, by NR.sub.4 groups where R.sub.4 =C.sub.1-6 -alkyl, CH--OH groups, and/or one or more terminal methyl groups may be replaced by dialkyl-substituted amino groups having 1 to 6 carbon atoms, and R.sub.1 and R.sub.2 may form a joint ring in which one CH.sub.2 group may be replaced by an O atom or by an NR.sub.4 group, and R.sub.1 =R.sub.2 =R.sub.3 --CH.sub.2 --CH.sub.2 -- attached via a common nitrogen atom, and n=3-11, and 0.5-2 mol of amine A)-C) per mole of acid, andb) pyromellitic acid and/or trimellitic acid, 0.
    Type: Grant
    Filed: January 10, 1995
    Date of Patent: April 1, 1997
    Assignee: Huels Aktiengesellschaft
    Inventors: Rainer Gras, Elmar Wolf
  • Patent number: 5591811
    Abstract: 1-Imidazolylmethyl-2-naphthols are effective catalysts and accelerators for curing epoxy resins, said naphthol compounds providing epoxy resin systems with prolonged room-temperature stability and fast curing at temperatures of 110.degree.-150.degree. C.
    Type: Grant
    Filed: September 12, 1995
    Date of Patent: January 7, 1997
    Assignee: Ciba-Geigy Corporation
    Inventor: Yefim Blyakhman
  • 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: 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: 5560934
    Abstract: A cleavable epoxy resin composition suitable for encapsulating electronic chips comprising the cured reaction product of a diepoxide containing a cyclic anhydride curing agent and an amine promoter.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: October 1, 1996
    Assignee: International Business Machines Corporation
    Inventors: Ali Afzali-Ardakani, Stephen L. Buchwalter, Jeffrey D. Gelorme, Laura L. Kosbar, Bert H. Newman, Frank L. Pompeo
  • 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: 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: 5541283
    Abstract: This invention relates to improved on component polyepoxide resins having enhanced physical and elastic properties. The polyepoxides resins comprise a polyepoxide resin based on a polyglycidyl ether of a phenolic type compound and a latent amine curative. The improvement in the polyepoxide resin formulation comprises incorporating an ester component having monofunctional reactivity with an amine hydrogen and a latent amine curative having from 3 to 10, and preferably 3 to 5 epoxide reactive hydrogen atoms into the epoxy resin. The glycidyl ester of versatic acid is preferred.
    Type: Grant
    Filed: October 18, 1995
    Date of Patent: July 30, 1996
    Assignee: Air Products and Chemicals, Inc.
    Inventor: Dilipkumar N. Shah
  • Patent number: 5541000
    Abstract: A thermally-curable aromatic amine-epoxy composition comprises(a) at least one polyepoxy compound;(b) a curing amount of at least one aromatic polyamine compound; and(c) a catalytically effective amount of at least one cure accelerator compound which is a .pi.-electron acceptor, and which lowers the cure exotherm peak temperature (as measured by differential scanning calorimetry (DSC) at 10.degree. C. per minute) of the composition by at least about 8 percent relative to the corresponding composition without the cure accelerator. Such accelerator compounds moderate and/or accelerate the thermal curing of aromatic amine-epoxy resins, enabling cure to occur at lower temperatures and/or in shorter time periods than those required for the unaccelerated composition.
    Type: Grant
    Filed: July 1, 1994
    Date of Patent: July 30, 1996
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Leslie C. Hardy, Wendy L. Thompson
  • 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