Two Or More Nitrogen-containing Reactants Patents (Class 528/120)
  • Patent number: 12018119
    Abstract: The present disclosure provides a copolyester including a dicarboxylic acid component A comprising a terephthalic acid residue or ester-forming derivative thereof, or a mixture thereof, and a 2,4-furandicarboxylic acid residue or ester-forming derivative thereof, or a mixture thereof, and a diol component B comprising an alkanediol residue having from 2 to 22 carbon atoms, wherein the dicarboxylic acid component A has a total molar content, and wherein the 2,4-furandicarboxylic acid residue or ester-forming derivative thereof, is present in an amount of from 0.1 to 10 mol %, with respect to the total molar content of the dicarboxylic acid component A. Inventive copolyesters have a slower crystallization rate, a higher gas barrier to CO2 and O2 and a higher ratio of 14C to 12C as measured by ASTM D6866 when compared to a comparable copolyester comprising isophthalic acid instead of 2,4-furandicarboxylic acid.
    Type: Grant
    Filed: January 27, 2022
    Date of Patent: June 25, 2024
    Assignee: BRASKEM S.A.
    Inventors: Felipe Cicaroni Fernandes, Iuri Estrada Gouvea, Bárbara Mano
  • Patent number: 11780986
    Abstract: The present invention provides methods for reducing extractables from plastic articles made from recycled plastic. The method includes the steps of: (a) providing a plastic article in a chamber; and (b) providing a fluorination gas in the chamber, thereby exposing the plastic article to the fluorination gas. The method results in the reduction of the extractables from the plastic article.
    Type: Grant
    Filed: January 28, 2022
    Date of Patent: October 10, 2023
    Assignee: Inhance Technologies, LLC
    Inventors: Siddharth Ram Athreya, Subramanian Iyer, Jad Darsey
  • Patent number: 11649319
    Abstract: The present invention provides a resin composition for a fiber-reinforced plastic, the resin composition including a cyanate ester (A), an epoxy resin (B), and an aromatic amine-based curing agent that is liquid at 25° C. (C), wherein the average number of cyanate groups in the cyanate ester (A) is 2.1 or greater, and/or the average number of epoxy groups in the epoxy resin (B) is 2.1 or greater. A fiber-reinforced plastic that is produced using this composition and a reinforcing fiber has favorable heat resistance and excellent tensile and bending properties, and therefore can be applied to a wide variety of fields including transport vehicles such as ships, automobiles, and aircrafts, sporting goods, building materials such as sinks and window frames, as well as industrial machinery and materials such as high-pressure gas tanks and blades for wind power generation.
    Type: Grant
    Filed: February 26, 2018
    Date of Patent: May 16, 2023
    Assignee: ADEKA CORPORATION
    Inventors: Masato Inadome, Naohiro Fujita, Kazuhide Morino
  • Patent number: 11472913
    Abstract: The present invention relates to an epoxy resin system containing an epoxy resin and a mono-alkylated diamine. The epoxy resin system can further contain a second amine. The present invention also relates to a method for producing an epoxy resin system comprising combining an epoxy resin with a mono-alkylated diamine. The mono-alkylated diamines of this invention enhance desirable processing and cured properties of epoxy resin compositions without the negative impact on mechanical properties in the cured product normally seen with cycloaliphatic amine-based curing agents.
    Type: Grant
    Filed: January 7, 2020
    Date of Patent: October 18, 2022
    Assignee: Evonik Operations GmbH
    Inventors: Gamini Ananda Vedage, Pritesh G. Patel, Jamie Schneck, Sebastian de Nardo, Steffen Kanzler
  • Patent number: 11434380
    Abstract: Provided are aqueous primer compositions and methods that can be useful for protecting primary structures on an aircraft. The primer composition can contain a thermosetting resin dispersion in water, a coalescent solvent in which the thermosetting resin is at least partially soluble, a first curative that is substantially water-insoluble, and a second curative that is substantially water-soluble. Optionally, the primer composition further contains an epoxy silane, where the primer composition is substantially free of any liquid or water-soluble curatives containing a primary or secondary amine group.
    Type: Grant
    Filed: March 22, 2018
    Date of Patent: September 6, 2022
    Assignee: 3M Innovative Properties Company
    Inventors: Lianzhou Chen, Jung-Sheng Wu, Michael S. Newman
  • Patent number: 11319435
    Abstract: A thermosetting resin composition at least including: [A] an epoxy resin containing two or more glycidyl groups; [B] a cyanate ester resin containing two or more cyanate groups; and [C] an amine compound; and satisfying the following conditions (1) and (2): (1) 0.25?the number of moles of glycidyl groups in the thermosetting resin composition/the number of moles of cyanate groups in the thermosetting resin composition?1.5; and (2) 0.05?the number of moles of active hydrogen contained in the amino groups in the thermosetting resin composition/the number of moles of cyanate groups in the thermosetting resin composition<0.5; and a prepreg and a fiber reinforced composite material using the thermosetting resin composition.
    Type: Grant
    Filed: February 6, 2019
    Date of Patent: May 3, 2022
    Assignee: TORAY INDUSTRIES, INC.
    Inventors: Jun Misumi, Ginpei Machida, Hiroaki Sakata
  • Patent number: 9440884
    Abstract: An epoxy grout system comprises a first epoxy resin component comprising a novolac epoxy resin, a bisphenol F epoxy resin, and a non-reactive diluent, and a second epoxy curing agent component comprising an amidoamine. The epoxy grout system has excellent chemical resistance while maintaining good installation properties. Another epoxy grout system comprises a first epoxy resin component which is resistant to a mixture of oleic acid and water, a second epoxy resin component which is less resistant to a mixture of oleic acid and water than the first component, and a third amine-containing curing agent component operable to cure both the first and second epoxy resin components. Optionally, the curing agent component can be provided as a plurality of amine-containing curing agent components of respective colors, whereby a user can select a curing agent component of a desired color for use with either the first or second epoxy resin component.
    Type: Grant
    Filed: May 28, 2014
    Date of Patent: September 13, 2016
    Assignee: CUSTOM BUILDING PRODUCTS, INC.
    Inventor: Anthony D. Pham
  • Patent number: 8980979
    Abstract: A curable composition including (a) at least one cyclic diamine, (b) at least one non-heterocyclic amine that has a pKa value of approximately 9.5 to about 12 at 25° C. for the most basic amine group in the non-heterocyclic amine molecule, (c) at least one epoxy resin, and (d) at least one alkylated phenol; (i) wherein the equivalents of the amine hydrogens from the cyclic diamine compared to the total amine hydrogens from both the cyclic diamine and the non-heterocyclic amine in the composition are greater than about 5%; (ii) wherein the ratio of the equivalents of the total amine hydrogens in the composition to the equivalents of the total epoxies in the composition is greater than or equal to about 1; and (iii) wherein the alkylated phenol is in an amount greater than about 10 wt % of the curable composition.
    Type: Grant
    Filed: February 16, 2010
    Date of Patent: March 17, 2015
    Assignee: Dow Global Technologies LLC
    Inventors: Marvin L. Dettloff, James R. Lowrey, Hemant A. Naik, Maurice J. Marks
  • Patent number: 8921497
    Abstract: An adhesive for anchoring materials in or to concrete or masonry exhibits a shorter cure time than previous adhesives and comprises an epoxy compound and a curing agent of at least one aliphatic amine and at least one tertiary amine, optionally with a reactive dilent, which possesses sufficent strength to pass ICBO Heat Creep Test at 110 degrees F. and the ICBO Damp Hole Test at 75 degrees F.
    Type: Grant
    Filed: December 27, 2002
    Date of Patent: December 30, 2014
    Assignee: Illinois Tool Works Inc.
    Inventor: Jim Surjan
  • Publication number: 20140155556
    Abstract: This invention relates to adhesive systems using imines and salts thereof, precursors to electron deficient olefins and coreactants therefor.
    Type: Application
    Filed: February 10, 2014
    Publication date: June 5, 2014
    Applicant: Henkel IP & Holding GmbH
    Inventors: Ciaran B. McArdle, Ligang Zhao
  • Patent number: 8633293
    Abstract: A polymer includes a reaction product of an epoxy resin, a first crosslinking agent, and a second crosslinking agent. The first crosslinking agent is reactive with the epoxy resin and has a first molecular weight. The second crosslinking agent is reactive with the epoxy resin and has a second molecular weight of at least 2.5 times greater than the first molecular weight. The polymer has a first phase having a first glass transition temperature at which the polymer is transformable between a first shape and a second shape. The second crosslinking agent is crystallizable within the polymer and thereby has a melting temperature that is detectable within the polymer.
    Type: Grant
    Filed: November 30, 2010
    Date of Patent: January 21, 2014
    Assignee: GM Global Technology Operations LLC
    Inventor: Ingrid A. Rousseau
  • Patent number: 8536284
    Abstract: The present invention provides N,N?-dimethyl secondary diamine polymers including methylamine-terminated poly-(N-methylazetidine) and methylamine-terminated poly-(N-methylazacycloheptane). Amine compositions and amine-epoxy compositions comprising N,N?-dimethyl secondary diamine polymers are also disclosed.
    Type: Grant
    Filed: January 19, 2010
    Date of Patent: September 17, 2013
    Assignee: Air Products & Chemicals, Inc.
    Inventors: Frederick Herbert Walker, Michael Ian Cook, Gamini Ananda Vedage, Robert Marjo Theodoor Rasing, Vipul P. Dholakia
  • Patent number: 8524807
    Abstract: Compounds VB of the formula (I) or (II), said compounds being particularly suitable as curing agents for epoxide resins. The compounds can be produced easily and rapidly. They can be used in the form of aqueous curing agents and form stabile aqueous emulsions in particular. This facilitates the formulation of ECC compounds for use primarily as coatings.
    Type: Grant
    Filed: June 12, 2009
    Date of Patent: September 3, 2013
    Assignee: Sika Technology AG
    Inventor: Pierre-André Bütikofer
  • Publication number: 20120178853
    Abstract: The present invention is a solventless one liquid type cyanate ester-epoxy resin composition having high thermal resistance as well as excellent storage stability and curing properties, which contains (A) cyanate ester, (B) epoxy resin, (C) guanidine compounds and (D) at least one kind of phenol compounds selected from a group consisting of phenol compounds represented by the following general formulae. In the general formulae, 1 is an integer selected from 0 to 4, R1 represents an unsubstituted or fluorine-substituted monovalent hydrocarbon group.
    Type: Application
    Filed: July 23, 2010
    Publication date: July 12, 2012
    Applicant: ADEKA CORPORATION
    Inventors: Ryo Ogawa, Shinsuke Yamada
  • Patent number: 8138288
    Abstract: This application is directed toward an improved method of synthesizing cationic siloxane prepolymers as well as a specific cationic siloxane prepolymer having improved compatibility with monofunctional siloxanyl methacrylate monomers and medical devices containing the cationic siloxane prepolymer.
    Type: Grant
    Filed: March 3, 2011
    Date of Patent: March 20, 2012
    Assignee: Bausch & Lomb Incorporated
    Inventors: Jason K. Stanbro, Ivan M. Nunez, Jay F. Kunzler, Derek A. Schorzman
  • Patent number: 8093340
    Abstract: A reversible adhesive system for coupling together two objects may consist of two shape memory polymers with molecular “hooks and loops” on the surfaces (i.e. the surface away from each of the objects). Utilizing the shape memory properties of the polymers, the molecular hooks and molecular loops may be brought together to form non-covalent bonds, leading to macroscopic adhesion. Upon heating, the adhesive bond can be separated with a small peeling force. The adhesive bonding and debonding can be repeated for multiple cycles with significant adhesion retention.
    Type: Grant
    Filed: July 24, 2008
    Date of Patent: January 10, 2012
    Assignee: GM Global Technology Operations LLC
    Inventors: Tao Xie, Ruomiao Wang, Xingcheng Xiao
  • Patent number: 8067523
    Abstract: It is an object of the present invention to provide a thermosetting resin composition having satisfactory adhesiveness, good processability, high heat resistance, and excellent dielectric characteristics in the GHz band; and a laminate and a circuit board including the thermosetting resin composition. The present invention provides a thermosetting resin composition including an imide oligomer component (A) containing at least one imide oligomer having a specific structure and an epoxy resin component (B) containing at least one epoxy resin. Furthermore, the present invention provides the thermosetting resin composition further including a polyimide resin component (C).
    Type: Grant
    Filed: October 4, 2006
    Date of Patent: November 29, 2011
    Assignee: Kaneka Corporation
    Inventors: Shigeru Tanaka, Kanji Shimoohsako, Takashi Ito, Mutsuaki Murakami
  • Patent number: 7993751
    Abstract: The present invention provides epoxy curing agent compositions comprising alkylated aminopropylated methylene-di-(cyclohexylamine) compounds. Amine-epoxy compositions and articles produced from these amine-epoxy compositions are also disclosed.
    Type: Grant
    Filed: August 6, 2008
    Date of Patent: August 9, 2011
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Gamini Ananda Vedage, Williams Rene Raymond, Maw Lin Foo
  • Patent number: 7951897
    Abstract: This application is directed toward an improved method of synthesizing cationic siloxane prepolymers as well as a specific cationic siloxane prepolymer having improved compatibility with monofunctional siloxanyl methacrylate monomers and medical devices containing the cationic siloxane prepolymer.
    Type: Grant
    Filed: January 24, 2008
    Date of Patent: May 31, 2011
    Assignee: Bausch & Lomb Incorporated
    Inventors: Jason K. Stanbro, Ivan M. Nunez, Jay F. Kunzler, Derek A. Schorzman
  • Patent number: 7893136
    Abstract: A water soluble polymer comprising a copolyhydroxyaminoether having side-chains of polyalkylene oxides, an aqueous solution of said polymer and process for preparing the copolyhydroxyaminoether.
    Type: Grant
    Filed: November 25, 2009
    Date of Patent: February 22, 2011
    Assignee: Dow Global Technologies, Inc.
    Inventors: Terry W. Glass, William J. Harris, Jerry E. White, Mike Cavitt, David C. Jammer, Louis A. Willy, Jr.
  • Patent number: 7868067
    Abstract: One aspect of the current invention is a halogen containing epoxy composition and a method of producing the same. A functional halogen group, fluorine in one case, is incorporated into an epoxy coating by using a functionalized amine curing agent in small amounts. Functionalized amine curing agents are cheaper and easier to produce from small amine precursors when compared to the cost and complexity of functionalizing bulky epoxy resins. Amine curing agents are incorporated into a cured epoxy network. However, many functional groups will affect the reactivity of the curing reaction due to electronegativity effects. By using small amounts of functionalized amines with a large amount of non-functionalized agent, the effect is small and in the case of migration, it can be advantageous for tribological, mechanical and other properties of epoxies and epoxy-containing materials.
    Type: Grant
    Filed: March 10, 2009
    Date of Patent: January 11, 2011
    Assignee: University of North Texas
    Inventors: Bryan Bilyeu, Witold Brostow, Kevin Menard
  • Patent number: 7786223
    Abstract: A curable composition comprising a) an epoxy resin containing on average more than one epoxy group per molecule, and b) as curing agent a composition comprising b1) 40-100 wt % of a reaction product from the reaction of b1a) at least one diglycidyl- and/or at least one monoglycidylether with b1b) a composition comprising a volatile monoamine and a polyamine, said composition b1b) is used in an amount to provide an excess amino groups relative to epoxy groups from b1a), and whereby the excess of monoamine is removed off from the reaction product, b2) 0-60 wt % of a polyamine, and b3) 0-25 wt % of a polyphenol novolac, and whereby the sum of components b1), b2) and b3) is 100 wt %, providing long pot life combined with fast cure times at low temperatures, thus making said compositions especially useful for marine and offshore coatings, industrial maintenance, construction, tank and pipe linings, adhesive, automobile and electrical potting applications.
    Type: Grant
    Filed: January 23, 2007
    Date of Patent: August 31, 2010
    Assignee: Huntsman International LLC
    Inventor: Isabelle Marie Marguerite Muller-Frischinger
  • Patent number: 7750107
    Abstract: A description is given of the use of asymmetrically substituted urea derivatives of the general formula (I) where R1 and R2 each independently are a linear or branched aliphatic hydrocarbon radical having 1 to 4 carbon atoms as accelerators in combination with dicyandiamide as latent hardener for epoxy resin systems based on unhalogenated or halogenated bisphenols of type A or F and also based on resorcinol or tetrakisphenylolethane. The advantages of the inventively proposed accelerator/hardener combination are, for example, the excellent reactivity and very good storage stability. Moreover, the mechanical properties of the resins cured accordingly are likewise outstanding.
    Type: Grant
    Filed: May 28, 2004
    Date of Patent: July 6, 2010
    Assignee: Alzchem Trostberg GmbH
    Inventors: Björn Antelmann, Sylvia Huber, Thomas Güthner
  • Patent number: 7709582
    Abstract: An embodiment of the invention relates to an epoxy resin composition for fiber reinforced composite material having an epoxy resin that is liquid at room temperature (component 1), aromatic polyamine that is liquid at room temperature (component 2) and diaminodiphenylsulfone (component 3). The proportion of component (1) relative to the entire epoxy resin in the composition is 60-100 wt %. The sum of the proportions of components (2) and (3) relative to the entire polyamine in the composition is 70-100 wt %. The proportion of component (3) relative to the entire polyamine in the composition is 25-60 wt %. The stoichiometric ratio of the entire polyamine to the entire epoxy resin in the composition is 0.7-1.3. Additional embodiments of the invention relate to other aspects of the invention.
    Type: Grant
    Filed: June 6, 2007
    Date of Patent: May 4, 2010
    Assignee: Toray Industries, Inc.
    Inventors: Shinji Kouchi, Mariko Ishikawa, Hiroki Oosedo, Go Tanaka, Toshiya Kamae
  • Patent number: 7683154
    Abstract: Curing agent for epoxy resins, comprising A) 1-99 wt % of an adduct obtainable by reaction of a1) a polyethylene polyamine having up to five nitrogen atoms in the molecule, with a2) a monoglycidylether, wherein the adduct of a1) and a2) is isolated by removing the excessive polyethylene-polyamine, and B) 99-1 wt % of an amine compound having at least two reactive amine hydrogen atoms in the molecule, as well as curable compositions additionally comprising an epoxy compound and the use of said curable compositions for the preparation of moulded articles and sheet materials, as well as for applications in the field of adhesives and sealing compounds.
    Type: Grant
    Filed: November 7, 2006
    Date of Patent: March 23, 2010
    Assignee: Huntsman International LLC
    Inventor: Joerg Volle
  • Patent number: 7678872
    Abstract: A water soluble polymer comprising a copolyhydroxyaminoether having side-chains of polyalkylene oxides, an aqueous solution of said polymer and process for preparing the copolyhydroxyaminoether.
    Type: Grant
    Filed: July 1, 2008
    Date of Patent: March 16, 2010
    Assignee: Dow Global Technologies, Inc.
    Inventors: Terry W. Glass, William J. Harris, Jerry E. White, Mike Cavitt, David C. Jammer, Louis A. Willy, Jr.
  • Patent number: 7666954
    Abstract: The present invention provides N,N?-dimethyl secondary diamine polymers including methylamine-terminated poly-(N-methylazetidine) and methylamine-terminated poly-(N-methylazacycloheptane). Amine compositions and amine-epoxy compositions comprising N,N?-dimethyl secondary diamine polymers are also disclosed.
    Type: Grant
    Filed: October 20, 2006
    Date of Patent: February 23, 2010
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Frederick Herbert Walker, Michael Ian Cook, Gamini Ananda Vedage, Robert Marjo Theodoor Rasing, Vipul P. Dholakia
  • Patent number: 7572877
    Abstract: An object of the present invention is to provide a modified cyclic aliphatic polyamine having a low viscosity and a small content of unreacted polyamine which can provide, when it is used as a curing agent for epoxy resin, an epoxy resin composition having an improved workability without adding solvent or diluent and an excellent property of epoxy resin cure product. The above modified cyclic aliphatic polyamine is obtained by addition reaction of a cyclic aliphatic polyamine such as isophoronediamine and norbornanediamine and an alkenyl compound such as styrene. The modified cyclic aliphatic polyamine thus obtained is added in epoxy resin to be used as a curing agent for epoxy resin.
    Type: Grant
    Filed: October 22, 2007
    Date of Patent: August 11, 2009
    Assignee: Mitsubishi Gaschemical Company, Inc.
    Inventors: Takeshi Koyama, Tetsushi Ichikawa, Hisayuki Kuwahara, Masatoshi Echigo
  • Patent number: 7501461
    Abstract: One aspect of the current invention is a halogen containing epoxy composition and a method of producing the same. A functional halogen group, fluorine in one case, is incorporated into an epoxy coating by using a functionalized amine curing agent in small amounts. Functionalized amine curing agents are cheaper and easier to produce from small amine precursors when compared to the cost and complexity of functionalizing bulky epoxy resins. Amine curing agents are incorporated into a cured epoxy network. However, many functional groups will affect the reactivity of the curing reaction due to electronegativity effects. By using small amounts of functionalized amines with a large amount of non-functionalized agent, the effect is small and in the case of migration, it can be advantageous for tribological, mechanical and other properties of epoxies and epoxy-containing materials.
    Type: Grant
    Filed: April 12, 2005
    Date of Patent: March 10, 2009
    Assignee: University of North Texas
    Inventors: Bryan Bilyeu, Witold Brostow, Kevin Menard
  • Patent number: 7468454
    Abstract: The present invention relates to a process for preparing amino-functional polyurethane prepolymers by a) preparing an NCO-functional polyurethane prepolymer by reacting an excess of one or more di- and/or polyisocyanates with at least one isocyanate-reactive compound having a functionality of at least 1.5, b) reacting the free NCO groups of the resulting polyurethane prepolymer with at least one compound containing one or more silanol groups to obtain the corresponding silylurethanes, and then c) converting the silylurethanes to amino-functional polyurethane prepolymers by hydrolysis and/or alcoholysis with decarboxylation. The present invention also relates coatings, adhesives, sealants, casting compounds or moldings obtained from these amino-functional polyurethene prepolymers.
    Type: Grant
    Filed: June 30, 2005
    Date of Patent: December 23, 2008
    Assignee: Bayer MaterialScience AG
    Inventor: Michael Mager
  • Patent number: 7351784
    Abstract: A chip-packaging composition includes a thermosetting resin and at least one of an N-heterocyclic carbene adduct, an imidazole, and a cycloaliphatic amine hardener. The chip-packaging composition is applied to flip-chip technology during no-flow underfill mounting of the flip-chip to a mounting substrate. The mounting substrate can be further mounted on a board. A process includes formation of the chip-packaging composition. A method includes assembly of the chip-packaging composition with the flip-chip, and further can include assembly of the mounting substrate to a board. A computing system is also included that uses the chip-packaging composition.
    Type: Grant
    Filed: September 30, 2005
    Date of Patent: April 1, 2008
    Assignee: Intel Corporation
    Inventor: Stephen E. Lehman, Jr.
  • Patent number: 7189770
    Abstract: An amine curing component which can be used with various types of prepolymers including a urethane prepolymer having a reactive functional group of highly reactivity is provided. Also provided is a curable resin composition containing such curing component. This curable resin composition exhibits good surface and depth curability in the curing, and adjustment of pot life is also easy. The curing component contains an amino group-containing compound (A), a ketone compound (B), a ketimine compound (C), and water (D), and the curable resin composition contains this curing component.
    Type: Grant
    Filed: November 21, 2003
    Date of Patent: March 13, 2007
    Assignee: The Yokohama Rubber Co., Ltd.
    Inventors: Hiroyuki Okuhira, Akihito Kanemasa, Hiroyuki Hosoda
  • Patent number: 7087799
    Abstract: An object of the present invention is to provide a material which resolves the drawbacks associated with polyimide polymers, and yet retains the advantages offered by conventional polyimide polymers. An amino group containing phenol derivative of the present invention is represented by a general formula (1) show below, and the present invention also provides a polyimide precursor produced using such an amino group containing phenol derivative. (wherein, R1, R2 and R3, which may be the same or different, each represent an alkyl group of 1 to 9 carbon atoms, an alkoxy group of 1 to 10 carbon atoms, a COOR group (in which R represents an alkyl group of 1 to 6 carbon atoms) or a hydrogen atom; R4 and R5, which may be the same or different, each represent an alkyl group of 1 to 9 carbon atoms or a hydrogen atom; X represents —O—, —S—, —SO2—, —C(CH3)2—, —CH2—, —C(CH3)(C2H5)—, or —C(CF3)2—; and n represents an integer of 1 or greater).
    Type: Grant
    Filed: January 31, 2003
    Date of Patent: August 8, 2006
    Assignee: Gun Ei Chemical Industry Co., Ltd.
    Inventors: Takeshi Tsuihiji, Michiyasu Yamazaki
  • Patent number: 7019045
    Abstract: An object of the present invention is to provide a material which resolves the drawbacks associated with polyimide polymers, and yet retains the advantages offered by conventional polyimide polymers. An amino group containing phenol derivative of the present invention is represented by a general formula (1) show below, and the present invention also provides a polyimide precursor produced using such an amino group containing phenol derivative. (wherein, R1, R2 and R3, which may be the same or different, each represent an alkyl group of 1 to 9 carbon atoms, an alkoxy group of 1 to 10 carbon atoms, a COOR group (in which R represents an alkyl group of 1 to 6 carbon atoms) or a hydrogen atom; R4 and R5, which may be the same or different, each represent an alkyl group of 1 to 9 carbon atoms or a hydrogen atom; X represents —O—, —S—, —SO2—, —C(CH3)2—, —CH2—, —C(CH3)(C2H5)—, or —C(CF3)2—; and n represents an integer of 1 or greater).
    Type: Grant
    Filed: May 9, 2005
    Date of Patent: March 28, 2006
    Assignee: Gun Ei Chemical Industry Co., Ltd.
    Inventors: Takeshi Tsuihiji, Michiyasu Yamazaki
  • Patent number: 7014699
    Abstract: The invention relates to addition compounds of formula (1): in which: n is a number from 1 to 10; R1 and R2 are identical or different and are each a hydrogen atom or a saturated or unsaturated aliphatic radical having 1 to 4 carbon atoms; R3 and R4 are identical or different and are each a hydrogen atom or alkyl having 1 to 3 carbon atoms, and the bridge member (R3+R4) is in each case positioned ortho or meta in relation to the phenolic oxygen atom; Z represents a group —CH2—CH2—, —CH2—CH(CH3)—, —CH(CH3)—CH2— or a combination thereof; s is number from 1 to 200; B represents hydrogen, —CO—CH?CH—COOM, —COCH(SO3M)CH2COOM, —CO—CH2—CH(SO3M)—COOM, —SO3M, —SO2M and/or —PO3MM, whereby M is preferably a cation selected from the group Li+, Na+, K+, NH4+, HO—CH2—CH2—NH3+, (HO—CH2—CH2—)2NH2+ or (HO—CH2—CH2—)3NH+; and Y is a radical of an amine. The inventive addition compounds are used as dispersing agents of solids, for example, pigments, particularly in aqueous media.
    Type: Grant
    Filed: February 26, 2002
    Date of Patent: March 21, 2006
    Assignee: Clariant GmbH
    Inventors: Martin Alexander Winter, Hans Joachim Metz, Andreas Harz, Andreas Pfrengle
  • Patent number: 7008555
    Abstract: A curing agent for epoxy agent having N-phenyl-p-phenylenediamine(4-aminodiphenylamine). An epoxy resin combination having a main agent and a curing agent. The main agent has an epoxy resin. The curing agent has a N-phenyl-p-phenylenediamine(4-aminodiphenylamine).
    Type: Grant
    Filed: May 22, 2003
    Date of Patent: March 7, 2006
    Assignee: Applied Poleramic Inc.
    Inventors: Brian S. Hayes, Richard Moulton, Doyle Dixon, Leonid Vorobyev
  • Patent number: 7005185
    Abstract: An epoxy composition includes an epoxy resin, a latent curing agent, and a catalyst. The composition includes two epoxide groups per molecule, and the latent curing agent is preferably a dicyanopolyamide, and most preferably dicyandiamide. The catalyst includes 2,4-toluene bis dimethyl urea, preferably in a concentration exceeding 70% by weight. The composition can be used in prepregs. The relative concentrations of the epoxy resin, curing agent, and catalyst are selected to achieve desired properties, including specific curing times and temperatures, and glass transition temperatures that enable a cured resin composition to be removed from a mold after being heated to its curing temperature, without being cooled. Exemplary formulations have reduced cure times, at both high and low curing temperatures, as compared to prior art formulations.
    Type: Grant
    Filed: November 27, 2002
    Date of Patent: February 28, 2006
    Assignee: Toray Composites (America), Inc.
    Inventors: Wei (Helen) Li, Kishio Miwa
  • Patent number: 6908982
    Abstract: An object of the present invention is to provide an amino composition which provides, when used as a curing agent for epoxy resin, a long pot life and an excellent appearance of a coating film to an epoxy resin composition without deteriorating the reactivity of the composition. The amino composition is obtained by addition reaction of diamine such as metaxylylenediamine and 1,3-bis(aminomethyl) cyclohexane and styrene, wherein the content of the diamine is less than 15% by weight based upon the total weight of the amino composition and the content of 1-addition product of having one phenethyl group is 50 to 100% by weight based upon the total weight of amino compound(s) obtained by the addition reaction.
    Type: Grant
    Filed: June 18, 2003
    Date of Patent: June 21, 2005
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Tetsushi Ichikawa, Hisayuki Kuwahara, Masatoshi Echigo
  • Patent number: 6841650
    Abstract: There is disclosed a crystallizable poly(2,5-di-substituted-1,4-phenylene oxide), which exhibits an exothermic peak for crystallization of not less than 5 J/g at 150° C. or over when cooled after melting, and/or an endothermic peak, at the time of melting of crystals thereof, of not less than 5 J/g at 150° C. or over when re-heated after cooling of the melt, and which comprises a recurring unit of the following formula (I), and a method of preparing the same by polymerization of a 2,5-di-substituted-phenol of the following formula (II) by use of a copper complex catalyst made of a tridentate ligand of which nitrogen atoms coordinate to a copper atom in coexistence with oxygen: wherein R1's independently represent a hydrocarbon group or a substituted hydrocarbon group, and they may be the same or different. The crystallizable poly(2,5-di-substituted-1,4-phenylene oxide) is able to provide a melt molding which has a reduced degree of coloration and good heat resistance.
    Type: Grant
    Filed: May 31, 2002
    Date of Patent: January 11, 2005
    Assignees: National Institute of Advanced Industrial Science and Technology, Japan Chemical Innovation Institute
    Inventors: Hideyuki Higashimura, Kiyoshi Fujisawa, Yoshihiko Moro-Oka, Shiro Kobayashi
  • Patent number: 6838176
    Abstract: Epoxy resin compositions comprising (a) an epoxy resin, (b) a latent curing agent with curing power at 100° C. or below and (c) an aromatic amine-based curing agent and/or an alicyclic amine-based curing agent, which are curable in two stages, or epoxy resin compositions further comprising (d) a curing accelerator, as well as a prepregs comprising reinforcing fiber materials impregnated with the epoxy resin compositions. The compositions give die-releasable cured products by primary curing at low temperature, give highly heat-resistant cured products by secondary curing, and exhibit satisfactory stability at room temperature.
    Type: Grant
    Filed: April 20, 2001
    Date of Patent: January 4, 2005
    Assignee: Mitsubishi Rayon Co., Ltd.
    Inventors: Kazuya Goto, Shigetsugu Hayashi, Tadayoshi Saito, Takashi Kaneko, Kazutami Mitani, Koki Wakabayashi, Yasuo Takagi
  • Patent number: 6660386
    Abstract: A primer for flame sprayed polyolefin comprises an epoxy resin, preferably of low molecular weight and/or low viscosity; and an amine hardener, part of which becomes highly reactive on exposure to open flame, providing near instant cure of the composition under flame spray conditions. The invention is unique that it provides strong adhesion to steel, even where the surface preparation is less than ideal, as well as to concrete and other substrates. The primer eliminates the need to preheat the substrate. The primer has strong adhesion to the topcoat polyolefinic material, especially to a functionalized topcoat. The composition withstands open flame and does not char under polyolefin flame spray conditions, nor does it run or sag, and it is not prone to failure as it cools after the application of the polyolefin.
    Type: Grant
    Filed: May 21, 2001
    Date of Patent: December 9, 2003
    Assignee: Polymer Ventures, L.L.C.
    Inventor: Shah A. Haque
  • Patent number: 6653369
    Abstract: Water dilutable amine curing agents for aqueous epoxy resin dispersions, comprising a combination of an epoxide-amine adduct with an emulsifier, the epoxide-amine adduct being obtainable by reacting a polyepoxide with a reaction product of an amine and an epoxide component or an amine and subsequent reaction with an epoxide component, the amount of amine being chosen such that the number of nitrogen-attached hydrogen atoms the number of epoxide groups by a factor of from 2 to 10, and the emulsifier being obtainable by reacting diepoxides or polyepoxides with compounds that are at least difunctional with respect to epoxides, optionally with compounds D that are monofunctional with respect to epoxides, and with amines G which contain at least one tertiary and at least one primary or at least two secondary amino group(s).
    Type: Grant
    Filed: May 6, 2002
    Date of Patent: November 25, 2003
    Assignee: Solutia Austria GmbH
    Inventors: Martin Gerlitz, Thomas Fischer, Andreas Gollner, Manfred Gogg, Elfriede Prucher, Heike Schneeberger, Josef Wenzl
  • Patent number: 6583528
    Abstract: A flywheel system for storing and delivering on demand electrical energy includes a flywheel supported for high speed rotation on bearings in a vacuum enclosure, and a motor-generator for spinning the flywheel up to speed and then for converting the rotational inertia in the flywheel back to electrical power. The flywheel includes a solid steel hub and a rim having only two rings press-fit on the hub with an interference fit. The rings are filament wound construction made primarily from standard modulus carbon fiber/epoxy. The steel hub stores between 40% and 60% of the energy in the flywheel. The press-fitting of the rings on the hub creates radial interference pressure between the hub and each of the composite rings that is greater than 5 ksi when at rest. The outer carbon fiber/epoxy ring is radially thinner than the inner ring, and both the hub outer diameter and the inner diameter of the assembled composite rim are tapered with the same angle.
    Type: Grant
    Filed: May 23, 2001
    Date of Patent: June 24, 2003
    Assignee: Indigo Energy, Inc.
    Inventor: Christopher W. Gabrys
  • Patent number: 6541596
    Abstract: There is disclosed a crystallizable poly(2,5-di-substituted-1,4-phenylene oxide), which exhibits an exothermic peak for crystallization of not less than 5 J/g at 150° C. or over when cooled after melting, and/or an endothermic peak, at the time of melting of crystals thereof, of not less than 5 J/g at 150° C. or over when re-heated after cooling of the melt, and which comprises a recurring unit of the following formula (I), and a method of preparing the same by polymerization of a 2,5-di-substituted-phenol of the following formula (II) by use of a copper complex catalyst made of a tridentate ligand of which nitrogen atoms coordinate to a copper atom in coexistence with oxygen: wherein R1's independently represent a hydrocarbon group or a substituted hydrocarbon group, and they may be the same or different. The crystallizable poly(2,5-di-substituted-1,4-phenylene oxide) is able to provide a melt molding which has a reduced degree of coloration and good heat resistance.
    Type: Grant
    Filed: February 1, 2000
    Date of Patent: April 1, 2003
    Assignees: Secretary of Agency of Industrial Science and Technology, Japan Chemical Innovation Institute
    Inventors: Hideyuki Higashimura, Kiyoshi Fujisawa, Yoshihiko Moro-oka, Shiro Kobayashi
  • Patent number: 6525159
    Abstract: This invention provides a one-part, room temperature moisture curable resin composition which comprises a ketimine prepared by reacting a ketone having a substituent at &agr; position and a polyamine having at least two amino groups within its molecule wherein &agr; position is methylene, and a main polymer which is an epoxy resin and/or a modified silicone having at least two hydrolyzable alkoxysilyl groups in its molecule, and which exhibits good shelf stability and high curing rate once taken out of the container, and which may further exhibit flexibility; a one-part, room temperature moisture curable resin composition which exhibits good shelf stability and curability as well as wet surface adhesion or initial thixotropic properties; a silicon containing compound having ketimine group whose reaction with the epoxy resin during the storage is prevented by the presence of a bulky alkyl group near the ketimine group and which exhibits good shelf stability and curability, and its production method; a one-part
    Type: Grant
    Filed: March 30, 1999
    Date of Patent: February 25, 2003
    Assignee: The Yokohama Rubber Co., Ltd.
    Inventors: Hiroyuki Okuhira, Naoya Adachi, Kazunori Ishikawa, Toshimitsu Takeda, Yo Kotani
  • Patent number: 6492437
    Abstract: Solvent-based processes for producing latent curing catalysts without causing an extreme exotherm. The process of the present invention includes combining an amine compound curing agent with a solvent, heating the mixture, adding an epoxy/solvent mixture via slow addition, removing the solvent and then heating the remaining composition. Following the heating, a phenolic resin is added to produce the final catalyst. The final catalyst comprises an amine compound, an epoxy, phenolic resin and a solvent. Catalysts having differing properties may be produced by varying the elements of the catalyst.
    Type: Grant
    Filed: June 21, 2001
    Date of Patent: December 10, 2002
    Assignee: National Starch and Chemical Investment Holding Corporation
    Inventors: Osama M. Musa, Michael J. Cipullo
  • Publication number: 20020183475
    Abstract: There is disclosed a crystallizable poly(2,5-di-substituted-1,4-phenylene oxide), which exhibits an exothermic peak for crystallization of not less than 5 J/g at 150° C. or over when cooled after melting, and/or an endothermic peak, at the time of melting of crystals thereof, of not less than 5 J/g at 150° C.
    Type: Application
    Filed: May 31, 2002
    Publication date: December 5, 2002
    Applicant: Secretary of Agency of Industrial Science and Technology
    Inventors: Hideyuki Higashimura, Kiyoshi Fujisawa, Yoshihiko Moro-Oka, Shiro Kobayashi
  • Patent number: 6458993
    Abstract: The present invention relates to novel aromatic cyanate ester compounds containing at least two rings linked by a group containing an unsaturated group. The present invention further relates to compositions and prepolymers of said novel aromatic cyanate ester compounds. The present invention further relates to a process for preparing said compounds and cured articles resulting from curable mixtures thereof.
    Type: Grant
    Filed: January 31, 2001
    Date of Patent: October 1, 2002
    Assignee: Vantico Inc.
    Inventors: Bor-Sheng Lin, Michael James Amone
  • Patent number: 6410127
    Abstract: An epoxy resin composition having a low viscosity around a room temperature and excellent reinforcing fiber impregnating properties provides a composite material having excellent heat resistance and mechanical properties including compressive strength. The epoxy resin composition includes an aromatic epoxy resin having at least di-functionality, an aromatic amine compound and/or an alicyclic amine compound, wherein 5 minutes after the main agent comprising the epoxy resin and the curing agent comprising the aromatic amine compound and/or the alicyclic amine compound are mixed, the composition shows a viscosity at 25° C. in the range of from 1 to 1500 mPa sec, and Tc, tc, and Tg satisfy the following equation (1): Tg≧Tc+20−k×(Tc−90)  (1), wherein k=0 when 60≦Tc<90 and k=0.35 when 90≦Tc≦200; Tc is the highest temperature (°C.
    Type: Grant
    Filed: November 8, 2001
    Date of Patent: June 25, 2002
    Assignee: Toray Industries, Inc.
    Inventors: Toshiya Kamae, Hiroki Oosedo, Shunsaku Noda, Shinji Kouchi, Ryuji Sawaoka
  • 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.