Patents Examined by Michael J. Feely
  • Patent number: 11370876
    Abstract: The present invention relates to a low-alkylphenol composition comprising a) at least one epoxy resin, b) at least one amine having at least two secondary amino groups that are both part of an organic ring system, and c) at least one salt of a strong Brønsted acid with a counterion selected from metal ions, metal-containing ions, phosphonium ions and ammonium ions, to processes for production thereof and to the use thereof.
    Type: Grant
    Filed: May 10, 2019
    Date of Patent: June 28, 2022
    Assignee: Evonik Operations GmbH
    Inventors: Emmanouil Spyrou, Dirk Fuchsmann, Britta Kohlstruk, Annette Sandkühler
  • Patent number: 11359048
    Abstract: The present invention provides a composition comprising a) at least one epoxy resin, b) at least one cyclic amine of the formula (I) in which R1 to R4 is H or an organic radical, with the proviso that at least one of the R1, R2, R3 and R4 radicals ?H, and X?—(Y1)m-(A1)n-(Y2)o-(A2)p-(Y3)q-(A3)r-(Y4)s—??(II) where, independently of one another, m, n, o, p, q, r and s=0 or 1, A1, A2, A3=alkylene or alkenylene radical and Y1, Y2, Y3, Y4?NR5, PR5, O or S, where R5 independently=organic radical, where any two organic radicals selected from R1 to R5 and any radicals present in the alkylene and/or alkenylene radicals A1, A2, A3 may also form one or more further rings, with the proviso that at least one of the radicals selected from R1 to R5 present and any radicals present in the alkylene and/or alkenylene radicals A1, A2, A3 is substituted by at least one —NHR6 or —NH2 group, where R6=organic radical, and c) at least one salt of a strong Brønsted acid with a counterion selected from metal ions, metal-co
    Type: Grant
    Filed: May 10, 2019
    Date of Patent: June 14, 2022
    Assignee: Evonik Operations GmbH
    Inventors: Emmanouil Spyrou, Dirk Fuchsmann, Britta Kohlstruk, Annette Sandkühler
  • Patent number: 11345777
    Abstract: Provided are an epoxy resin composition, a prepreg, a resin sheet, and a carbon fiber-reinforced composite material, which have high heat resistance, a high elastic modulus, low water absorption, and excellent flame resistance. This epoxy resin is a para-cresol novolac epoxy resin represented by General formula (1), in which a content ratio of components represented by n=1 as measured by gel permeation chromatography is less than 10% by area, and a content ratio of components represented by n=2 as measured by gel permeation chromatography is at least 1% by area and less than 40% by area. (In the formula, plural R's each independently represent a C1-6 alkyl group, n represents a real number of 1 to 10, and G represents a substituted or unsubstituted glycidyl group.
    Type: Grant
    Filed: July 23, 2019
    Date of Patent: May 31, 2022
    Assignee: NIPPON KAYAKU KABUSHIKI KAISHA
    Inventors: Yusuke Kawano, Masataka Nakanishi, Kazuma Inoue
  • Patent number: 11345780
    Abstract: A thermoplastic polyester resin composition includes a thermoplastic polyester resin (A), an epoxy compound (B) having an epoxy equivalent of from 200 to 3,000 g/eq, and a hydroxy group-containing resin (C) having a number average molecular weight of from 2,000 to 500,000 and a halogen element content of 1,000 ppm or less, wherein the epoxy compound (B) is blended in an amount of from 0.05 to 10 parts by weight with respect to 100 parts by weight in total of 70 to 99.9 parts by weight of the thermoplastic polyester resin (A) and 0.1 to 30 parts by weight of the hydroxy group-containing resin (C). The thermoplastic resin composition and a molded article achieve both long-term hydrolysis resistance and heat aging resistance at a high level, and can further suppress bleed-out to the surface of the molded article during heat-dry and heat-moisture treatments.
    Type: Grant
    Filed: June 20, 2018
    Date of Patent: May 31, 2022
    Assignee: Toray Industries, Inc.
    Inventors: Kenichi Okunaga, Yusuke Tojo, Makito Yokoe, Hideyuki Umetsu
  • Patent number: 11345808
    Abstract: The present invention aims to provide an epoxy resin composition that is high in both fast curability and storage stability, a prepreg prepared by using the epoxy resin composition, and a fiber reinforced composite material prepared by curing the prepreg. The epoxy resin composition contains the following components [A], [B], [C], and [D] and meets the following requirements [a], [b], and [c]: [A]: epoxy resin, [B]: dicyandiamide, [C]: aromatic urea, [D]: borate ester, [a]: 0.014?(content of component [D]/content of component [C])?0.045, [b]: 0.9?(number of moles of active groups in component [A]/number of moles of active hydrogen in component [B])?1.2, and [c]: 14?(content of component [A]/content of component [C])?25.
    Type: Grant
    Filed: July 18, 2018
    Date of Patent: May 31, 2022
    Assignee: TORAY INDUSTRIES, INC.
    Inventors: Eiki Takahashi, Daisuke Konishi, Masayuki Miyoshi, Noriyuki Hirano
  • Patent number: 11332607
    Abstract: Formulations comprising from 10 to 80% by weight of the formulation of a halogenated epoxy resin; from 1 to 15% by weight of the formulation of an antimony based fire retardant; from 1 to 10% by weight of the formulation of an inorganic or non-polymeric organic phosphorous containing fire retardant; and from 1 to 30% by weight of the formulation of a curative system are provided. The formulations are particularly suitable for producing aircraft interior composite components having good fire retarding properties, low smoke emission, low smoke toxicity and low heat release properties. The formulations also have excellent processing and mechanical properties. Further components may be included in the compositions to improve various properties, including the fire retarding, low smoke emission, low smoke toxicity and low heat release properties and to also further improve the processing and mechanical properties, including toughness.
    Type: Grant
    Filed: June 13, 2019
    Date of Patent: May 17, 2022
    Assignee: HEXCEL COMPOSITES LIMITED
    Inventor: Dana Blair
  • Patent number: 11332571
    Abstract: A slow reacting epoxy resin system is disclosed. The slow reacting epoxy resin system comprises a high purity epoxy resin component selected from the group comprising of a high purity Bisphenol A(BPA), a high purity Bisphenol F (BPF), and a combination thereof, and an amine curing agent. The initial viscosity after mixing the high purity epoxy resin component and the amine curing agent is less than 350 mPa·s at 25° C.
    Type: Grant
    Filed: September 14, 2018
    Date of Patent: May 17, 2022
    Assignee: ADITYA BIRLA CHEMICALS (THAILAND) LTD.
    Inventors: Pradip Kumar Dubey, Amit Dixit, Sirirat Changmongkol, Kanchana Inchamnan, Wasinee Sakathok
  • Patent number: 11319467
    Abstract: Self-healing mircrocapsules including: a) a polymeric shell; b) a healing-agent compartmentalized inside the polymeric shell; and c) a catalyst deposited on the surface of the polymeric shell; where the microcapsules are prepared by suspension polymerization, and the microcapsules may be present in a polymeric matrix and in composite materials that include such polymeric matrix.
    Type: Grant
    Filed: December 13, 2017
    Date of Patent: May 3, 2022
    Assignee: FUNDACIÓN TECNALIA RESEARCH & INNOVATION
    Inventors: Raquel Rodriguez Alonso, Sonia Florez Fernandez
  • Patent number: 11319465
    Abstract: The provided relates to a method for preparing an anisotropic conductive adhesive for fine pitch and an anisotropic conductive adhesive for fine pitch prepared by the same method. Provided is a method for preparing an anisotropic conductive adhesive for a fine pitch including: (i) removing an oxide film of solder particles having self-fusion and self-orientation functions between metal terminals of a substrate by melting the solder particles at a predetermined temperature using a first reducing agent; (ii) removing moisture generated in step (i); and (iii) preparing an anisotropic conductive adhesive by mixing the solder particles from which the oxide film and the moisture are removed with a binder resin in steps (i) and (ii), in which step (iii) is performed in a state where a contact with oxygen is blocked.
    Type: Grant
    Filed: February 6, 2017
    Date of Patent: May 3, 2022
    Inventor: Kyung Sub Lee
  • Patent number: 11319404
    Abstract: The present invention provides an epoxy compound indicated by chemical formula (1) (in chemical formula (1), X indicates a C1-10 aliphatic hydrocarbon group, R1 and R2 each independently indicate one selected from the group consisting of a hydrogen atom, an aliphatic hydrocarbon group, an aromatic group, an alkoxy group, and a halogen atom)
    Type: Grant
    Filed: August 7, 2019
    Date of Patent: May 3, 2022
    Assignee: TEIJIN LIMITED
    Inventors: Suguru Ozawa, Akimichi Oda, Hideaki Tominaga, Hiroaki Kuwahara
  • 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: 11319420
    Abstract: A prepreg containing the following constituent elements [A] to [C], wherein a resin composition containing the constituent elements [B] and [C] has a higher-order structure derived from a diffraction angle 2? between 1.0° and 6.0° observed with X-ray diffraction after curing: [A]: carbon fibers [B]: epoxy resin [C]: curing agent of [B].
    Type: Grant
    Filed: March 16, 2018
    Date of Patent: May 3, 2022
    Assignee: TORAY INDUSTRIES, INC.
    Inventors: Atsuhito Arai, Koji Furukawa, Atsuki Sugimoto, Masahiro Mino, Mayumi Mihara
  • Patent number: 11312829
    Abstract: A prepreg is provided. The prepreg is prepared by impregnating a liquid crystal polymer non-woven fabric with a thermal-curable resin composition or by coating a thermal-curable resin composition onto a liquid crystal polymer non-woven fabric and drying the impregnated or coated liquid crystal polymer non-woven fabric, wherein the thermal-curable resin composition includes: (A) an unsaturated monomer; and (B) a cyclic olefin copolymer including the following repeating units: (B-1) a repeating unit of formula (I), (B-2) a repeating unit of formula (II), and (B-3) a repeating unit of formula (III), R1 to R22, m, n, o, and p in formulas (I) to (III) are as defined in the specification, wherein based on the total moles of the repeating units (B-1) to (B-3), the content of the repeating unit (B-2) is 19 mol % to 36 mol %, and wherein the weight ratio of the cyclic olefin copolymer (B) to the unsaturated monomer (A) is 0.5 to 7.
    Type: Grant
    Filed: April 10, 2019
    Date of Patent: April 26, 2022
    Assignee: TAIWAN UNION TECHNOLOGY CORPORATION
    Inventors: Shur-Fen Liu, Chin-Hsien Hung
  • Patent number: 11312887
    Abstract: The present invention relates to a composition suitable as epoxy adhesive composition comprising a multistage polymer in form of polymeric particles and a (meth)acrylic polymer its process of preparation and its use. In particular the present invention relates to a structural epoxy adhesive composition comprising a multistage polymer in form of polymeric particles made by a multistage process and a (meth)acrylic polymer its process of preparation and its use. More particularly the present invention relates to structural (epoxy adhesive composition made from a two part composition or a one part composition comprising a multistage polymer in form of polymeric particles made by a multistage process and a (meth)acrylic polymer its process of preparation and its use.
    Type: Grant
    Filed: July 12, 2018
    Date of Patent: April 26, 2022
    Assignee: Arkema France
    Inventors: Philippe Hajji, Rosangela Pirri, Rabi Inoubli
  • Patent number: 11306239
    Abstract: A high thermal conductivity prepreg is provided. The high thermal conductivity prepreg includes a high thermal conductivity reinforcing material and a dielectric material layer formed on the surface of the high thermal conductivity reinforcing material, wherein the high thermal conductivity reinforcing material is prepared by a process which includes the following steps: (a) providing a precursor aqueous solution, the precursor aqueous solution includes a precursor selected from the group of organic salts, inorganic salts, and combinations thereof; (b) subjecting the precursor aqueous solution to a hydrolysis reaction to form an intermediate product aqueous solution; (c) subjecting the intermediate product aqueous solution to a condensation polymerization reaction to form a pretreatment solution; (d) impregnating a reinforcing material with the pretreatment solution; and (e) oven-drying the impregnated reinforcing material to obtain the high thermal conductivity reinforcing material.
    Type: Grant
    Filed: March 20, 2019
    Date of Patent: April 19, 2022
    Assignee: TAIWAN UNION TECHNOLOGY CORPORATION
    Inventors: Chih-Wei Liao, Chen-Hua Yu
  • Patent number: 11299620
    Abstract: The present invention relates to an epoxy resin composition (A) containing an epoxy resin represented by the following formula (1): and an epoxy resin represented by the following formula (2): wherein in formula (2), n represents an integer of from 0 to 2, wherein a content of the epoxy resin represented by formula (1) is from 0.01 to 0.99% by weight, and relates to an epoxy resin composition (B) containing a curing agent in an amount of from 0.01 to 1000 parts by weight relative to 100 parts by weight of the epoxy resin composition (A).
    Type: Grant
    Filed: June 10, 2020
    Date of Patent: April 12, 2022
    Assignee: Mitsubishi Chemical Corporation
    Inventor: Kazumasa Oota
  • Patent number: 11286336
    Abstract: A curing agent composition comprising anhydride and approximately equimolar amount of tertiary amine or imidazole and carboxylic acid, the amine being 1-piperidinylethanol (N-hydroxyethyl-piperidine, NHEP) represented by the structure below or an imidazole represented by the structure below: where R1=H, a C1-C20 straight chain or branched alkyl, or a monocyclic aryl; R2=a C1-C20 straight chain or branched alkyl, or a monocyclic aryl. The carboxylic acid is represented by RCOOH; R=a C1-C20 straight chain or branched alkyl, or a monocyclic aryl. The composition comprises a lower ratio of epoxy resin to anhydride (1:0.4-0.6) than typically used (1:0.8-1.1). In addition, it uses a higher loading of the hindered latent tertiary amine or the imidazole in combination with the carboxylic acid (wt % ratio of combined amine and carboxylic acid to anhydride ˜10%). With this composition a full cure can be achieved in less than 2 hr at a significantly lower temperature (˜100° C.).
    Type: Grant
    Filed: December 12, 2017
    Date of Patent: March 29, 2022
    Assignee: Evonik Operations GmbH
    Inventors: Pritesh G. Patel, Gauri Sankar Lal, Douglas M. La Comare
  • Patent number: 11279834
    Abstract: An ultra-high solids content primer coating composition comprising: (i) 5.0 to 50 wt % of at least one bisphenol F epoxy resin; (ii) 1.5 to 12 wt % of at least one silane; (iii) 0 to 20 wt % of at least one hydrocarbon resin; (iv) 0 to 15 wt % of at least one reactive diluent; (v) at least one curing agent; wherein said composition has a solids content of at least 90 wt % according to ASTM D5201-05; wherein said composition has a viscosity of 200 to 800 cps at 23° C. and 50% RH (ASTM D4287); and wherein the ratio between hydrogen equivalents in the curing agent and epoxy equivalents of the coating composition is in the range 50:100 to 120:100.
    Type: Grant
    Filed: September 8, 2017
    Date of Patent: March 22, 2022
    Assignee: JOTUN AS
    Inventors: Ku-sik Jung, Hyun-ho Shin, Erik Risberg
  • Patent number: 11279797
    Abstract: A curing agent for epoxy resin compositions containing at least one amine of formula (I) and at least one amine of formula (II). The curing agent is a low-odor, low-viscosity, low-toxicity curing agent and has a low propensity for carbamatization and a high reactivity toward epoxy resins. It enables low-odor and low-emission epoxy resin products which are readily processable and which even at low temperatures and high humidities undergo rapid and problem-free curing to afford high-quality plastics having a high hardness and a regular, non-tacky surface with high gloss.
    Type: Grant
    Filed: February 14, 2017
    Date of Patent: March 22, 2022
    Assignee: SIKA TECHNOLOGY AG
    Inventors: Edis Kasemi, Andreas Kramer, Ursula Stadelmann, Urs Burckhardt
  • Patent number: 11254793
    Abstract: The present invention provides thermosetting resin pre-impregnated or infused fiber materials or prepregs comprising a thermosetting resin mixture and a fiber material component of a heat resistant fiber, such as carbon fiber, having an areal weight of from 500 to 3,000 g/m2 having a coating of from 0.5 to 4 phr of a latent, particulate curative or solid curative, preferably, dicyandiamide, wherein the prepregs are infused with a thermosetting resin mixture comprising (a) at least one liquid epoxy resin, and (b) a hardener and/or a catalyst, as well as methods of making the same. The prepregs of present invention enables the simple provision of lightweight composites having consistent resin cure throughout.
    Type: Grant
    Filed: August 30, 2017
    Date of Patent: February 22, 2022
    Assignee: Dow Global Technologies LLC
    Inventors: David H. Bank, Richard Baumer, Kevin J. Bouck, Jun Cai, Marsha L. Langhorst, Abhijit A. Namjoshi, Weijun Wang