WO2023157750A1 - Composition de résine pour matière plastique renforcée par des fibres, et matière plastique renforcée par des fibres - Google Patents

Composition de résine pour matière plastique renforcée par des fibres, et matière plastique renforcée par des fibres Download PDF

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Publication number
WO2023157750A1
WO2023157750A1 PCT/JP2023/004329 JP2023004329W WO2023157750A1 WO 2023157750 A1 WO2023157750 A1 WO 2023157750A1 JP 2023004329 W JP2023004329 W JP 2023004329W WO 2023157750 A1 WO2023157750 A1 WO 2023157750A1
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Prior art keywords
fiber
resin composition
component
reinforced plastics
reinforced plastic
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PCT/JP2023/004329
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English (en)
Japanese (ja)
Inventor
一英 森野
直博 藤田
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株式会社Adeka
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Publication of WO2023157750A1 publication Critical patent/WO2023157750A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/50—Amines
    • C08G59/56—Amines together with other curing agents
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/04—Reinforcing macromolecular compounds with loose or coherent fibrous material

Definitions

  • the present invention relates to a resin composition for fiber-reinforced plastics and fiber-reinforced plastics using the composition, and more particularly, fiber-reinforced plastics containing epoxy resin, polyoxyalkylene polyamine, and a salt compound that is liquid at room temperature. Regarding.
  • thermosetting epoxy resin unsaturated polyester, polyamide resin, or phenolic resin
  • Fiber-reinforced plastics produced by this method are widely used as materials for structures such as aircraft and ships, and sporting goods such as tennis rackets and golf clubs.
  • Epoxy resin used as a reinforcing material is often used as a well-balanced material because it is not only excellent in adhesiveness, heat resistance, and chemical resistance, but also inexpensive.
  • Patent Documents 1 to 3, etc. propose an epoxy resin composition for fiber reinforcement consisting of an epoxy resin, an acid anhydride, and a curing catalyst, and describe an imidazole-based catalyst as the curing catalyst.
  • JP-A-8-156115 Japanese Unexamined Patent Application Publication No. 2008-38082 JP 2015-3938 A
  • an object of the present invention is to provide a resin composition for fiber-reinforced plastics that is suitable for improving the strength of fiber-reinforced plastics, has an excellent balance between pot life and curability, and has excellent non-coloring properties. That's what it is.
  • the inventors of the present invention have made intensive studies to achieve the above objects, and have developed a resin composition for fiber-reinforced plastics having excellent curability and non-coloring property by combining an epoxy resin, a polyoxyalkylene polyamine and a specific phosphonium salt.
  • the present invention was arrived at by discovering that a product can be obtained.
  • the present invention provides a fiber containing at least one compound selected from component (A): epoxy resin, component (B): polyoxyalkylene polyamine, and component (C): a compound represented by the following formula (1).
  • a resin composition for reinforced plastics is provided.
  • R 1 to R 6 each independently represent a hydrocarbon group having 1 to 10 carbon atoms, and X 1 to X 4 each independently represent an oxygen atom or a sulfur atom.
  • the present invention also provides a fiber-reinforced plastic containing the resin composition for fiber-reinforced plastics.
  • the resin composition for fiber-reinforced plastics of the present invention is excellent in curability and non-coloring properties, and the fiber-reinforced plastics obtained therefrom provide various moldings with excellent aesthetic appearance from the viewpoint of being excellent in non-coloring properties. It is possible.
  • epoxy resins as component (A) include polyglycidyl ether compounds of mononuclear polyhydric phenol compounds such as hydroquinone, resorcinol, pyrocatechol and phloroglucinol; methylenebis(orthocresol), ethylidenebisphenol, isopropylidenebisphenol (bisphenol A), isopropylidenebis(orthocresol), tetrabromobisphenol A, 1,3-bis(4-hydroxycumylbenzene), 1,4-bis( 4-hydroxycumylbenzene), 1,1,3-tris(4-hydroxyphenyl)butane, 1,1,2,2-tetra(4-hydroxyphenyl)ethane, thiobisphenol, sulfobisphenol, oxybisphenol, phenol Polyglycidyl ether compounds of polynuclear polyhydric phenol compounds such as novolac, ortho-cresol novolak, ethylphenol novolak, but
  • N,N-diglycidylaniline bis(4-(N-methyl-N-glycidylamino)phenyl)methane, diglycidylorthotoluidine, N,N-bis(2,3-epoxypropyl) -4-(2,3-epoxypropoxy)-2-methylaniline, N,N-bis(2,3-epoxypropyl)-4-(2,3-epoxypropoxy)aniline, N,N,N', Epoxy compounds having a glycidylamino group such as N'-tetra(2,3-epoxypropyl)-4,4-diaminodiphenylmethane; vinylcyclohexene diepoxide, cyclopentanediene diepoxide, 3,4-epoxycyclohexylmethyl-3, Epoxidized products of cyclic olefin compounds such as 4-epoxycyclohexanecarboxylate, 3,
  • these epoxy resins are those internally crosslinked with a prepolymer having an isocyanate terminal, or those having a high molecular weight with a polyvalent active hydrogen compound (polyhydric phenol, polyamine, carbonyl group-containing compound, polyphosphate ester, etc.). It's okay.
  • These epoxy resins may be used alone or in combination of two or more. In the present invention, an epoxy resin having an average of more than 1.1 epoxy groups per molecule is preferred, and an epoxy resin having two or more epoxy groups per molecule is particularly preferred.
  • the epoxy resins preferably contains at least one of a polyglycidyl ether compound of a polynuclear polyhydric phenol compound and a polyglycidyl ether compound of a polyhydric alcohol compound, and more preferably contains a polyglycidyl ether compound of a polynuclear polyhydric phenol compound. It is more preferable to contain a polyglycidyl ether compound of a polynuclear polyhydric phenol compound as a main component, and it is particularly preferable to contain a bisphenol type epoxy resin as a main component.
  • the main component means that the content in the epoxy resin is more than 50% by mass.
  • a bisphenol-type epoxy resin is one having a bisphenol structure such as a polyglycidyl ether compound of bisphenols such as bisphenol A.
  • a resin containing a bisphenol type epoxy resin as a main component is preferable because it provides excellent curability and physical properties of the cured product.
  • the resin composition of the present invention is used for fiber-reinforced plastics, it is preferable to use an epoxy resin that is liquid at 25° C. from the viewpoint of permeability into fiber materials.
  • the amount of the epoxy resin used is not particularly limited. ⁇ 80 parts by mass.
  • the polyoxyalkylene polyamine which is the component (B) used in the present invention, is a compound having a polyoxyalkylene skeleton and two or more amino groups, and there are no particular restrictions on its molecular structure, molecular weight, and the like.
  • polyoxyalkylene polyamine examples include polyoxypropylene diamine, trimethylolpropane poly(oxypropylene)triamine, glycerylpoly(oxypropylene)triamine, polyoxyethylenediamine, trimethylolpropanepoly(oxyethylene)triamine, glycerylpoly( oxyethylene) triamine and the like.
  • polyoxypropylenediamine as the component (B) from the viewpoint of improving curability and physical properties of the cured product.
  • the weight average molecular weight of the polyoxyalkylene polyamine which is the component (B) is preferably 200 to 5000, more preferably 200 to 2000, and particularly 200 to 500 is preferred.
  • the weight average molecular weight refers to the polystyrene equivalent weight average molecular weight (Mw) measured by gel permeation chromatography (GPC).
  • component (B) Commercially available products of component (B) include, for example, Huntsman's Jeffamine D-230, Jeffamine D-400, Jeffamine D-2000, Jeffamine D-4000, Jeffamine T-403, and Jeffamine T. -3000, Jeffamine T-5000 and the like.
  • the amount of polyoxyalkylene polyamine used as component (B) is preferably 1 to 50 parts by mass, particularly preferably 5 to 30 parts by mass, per 100 parts by mass of the epoxy resin as component (A).
  • the amount of polyoxyalkylene polyamine used as component (B) is preferably 1 to 50 parts by mass, particularly preferably 5 to 30 parts by mass, per 100 parts by mass of the epoxy resin as component (A).
  • the amount of the polyoxyalkylene polyamine used as the component (B) is not particularly limited, but is preferably 0.01 to 50% by mass, more preferably 0.05%, in the resin composition for fiber-reinforced plastics. to 40% by mass, particularly preferably 0.1 to 30% by mass.
  • the (C) component used in the present invention is a compound represented by the following formula (1) and functions as a curing catalyst for the (A) and (B) components.
  • R 1 to R 6 each independently represent a hydrocarbon group having 1 to 10 carbon atoms, and X 1 to X 4 each independently represent an oxygen atom or a sulfur atom.
  • examples of hydrocarbon groups having 1 to 10 carbon atoms represented by R 1 to R 6 include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, secondary Butyl group, tert-butyl group, pentyl group, hexyl group, heptyl group, octyl group, isooctyl group, tert-octyl group, 2-ethylhexyl group, nonyl group, isononyl group, decyl group, isodecyl group, phenyl group, benzyl group and a cyclohexyl group.
  • R 1 to R 4 are each independently preferably a methyl group or a butyl group
  • R 5 and R 6 are preferably each independently a methyl group or an ethyl group. This is because a resin composition having an excellent balance of curability and non-coloring property can be obtained.
  • Specific examples of preferred compounds represented by the general formula (1) as the component (C) include compounds represented by the following general formula (1a) or general formula (1b).
  • the compounding amount of the compound represented by the general formula (1), which is the component (C), is not particularly limited, but is 0.00 per 100 parts by mass of the polyoxyalkylene polyamine, which is the component (B). 01 to 20 parts by weight, preferably 0.05 to 15 parts by weight, particularly preferably 0.1 to 10 parts by weight.
  • component (C) By using 0.01 parts by mass or more of the compound represented by the general formula (1) as component (C), sufficient curability can be obtained, and by using 20 parts by mass or less, sufficient storage can be achieved. Stability can be obtained.
  • the amount of the compound represented by the general formula (1), which is the component (C), is not particularly limited, but is preferably 0.005 to 10% by mass in the resin composition for fiber-reinforced plastics, More preferably 0.01 to 8% by mass, particularly preferably 0.05 to 5% by mass.
  • the present invention further contains a silane coupling agent as the component (D) because good adhesion to the fiber material can be obtained.
  • the silane coupling agent include ⁇ -aminopropyltriethoxysilane, N- ⁇ -(aminoethyl)- ⁇ -aminopropyltriethoxysilane, N- ⁇ -(aminoethyl)-N'- ⁇ -( aminoethyl)- ⁇ -aminopropyltriethoxysilane, ⁇ -anilinopropyltriethoxysilane, ⁇ -glycidoxypropyltriethoxysilane, ⁇ -(3,4-epoxycyclohexyl)ethyltriethoxysilane, vinyltriethoxysilane , N- ⁇ -(N-vinylbenzylaminoethyl)- ⁇ -aminopropyltriethoxysilane, ⁇ -methacryloxyprop
  • ⁇ -aminopropyltrimethoxysilane and/or ⁇ -glycidoxypropyltrimethoxysilane are more preferably added because they are readily available and inexpensive. Most preferably, sidoxypropyltrimethoxysilane is added.
  • the amount of the silane coupling agent, component (D), is not particularly limited, but is 0.1 to 50 parts by mass with respect to 100 parts by mass of the epoxy resin, component (A). is preferred. From the viewpoint of good miscibility with the resin and improved adhesion to the fiber, it is particularly preferable to add 0.5 to 30 parts by mass, particularly 1 to 20 parts by mass.
  • the amount of the silane coupling agent used as the component (D) is not particularly limited, but is preferably 0.005 to 10% by mass, more preferably 0.01%, in the resin composition for fiber-reinforced plastics. to 8% by weight, particularly preferably 0.05 to 5% by weight.
  • a reactive diluent as component (E) may be used in combination in order to adjust the viscosity to a desired level.
  • the reactive diluent is incorporated into the cured product after the resin composition is cured, so that it does not affect the physical properties of the cured product.
  • Reactive diluents for epoxy resin compositions include diluents having an epoxy group in the molecule.
  • reactive diluents examples include n-butyl glycidyl ether, C 12 -C 14 alkyl glycidyl ether, allyl glycidyl ether, 2-ethylhexyl glycidyl ether, styrene oxide, phenyl glycidyl ether, cresyl glycidyl ether, Examples include monoglycidyl ether compounds such as p-sec-butylphenyl glycidyl ether, t-butylphenyl glycidyl ether, glycidyl methacrylate, and tertiary carboxylic acid glycidyl esters.
  • Additives may be used in combination with the resin composition for fiber-reinforced plastics of the present invention, if necessary.
  • the above additives include non-reactive diluents (plasticizers) such as dioctyl phthalate, dibutyl phthalate, benzyl alcohol and coal tar; pigments; candelilla wax, carnauba wax, Japan wax, ivory wax, beeswax, lanolin , spermaceti, montan wax, petroleum wax, fatty acid wax, fatty acid ester, fatty acid ether, aromatic ester, lubricant such as aromatic ether; thickener; thixotropic agent; antioxidant; light stabilizer; ultraviolet absorber ;flame retardants; antifoaming agents;
  • plasticizers such as dioctyl phthalate, dibutyl phthalate, benzyl alcohol and coal tar
  • pigments candelilla wax, carnauba wax, Japan wax, ivory wax, beesw
  • the resin composition for fiber-reinforced plastics of the present invention is used for fiber-reinforced plastics, it is preferably liquid at 25°C, and particularly preferably has a viscosity of 100 to 3000 Pa ⁇ s.
  • the resin composition for fiber-reinforced plastics of the present invention is suitable as a matrix resin for fiber-reinforced plastics having reinforcing fibers such as carbon fiber and glass fiber.
  • the type of reinforcing fiber is not particularly limited, and for example, carbon fiber, glass fiber, aramid fiber, boron fiber, alumina fiber, silicone carbide fiber, etc. may be used alone, or two or more types of hybrid fibers may be used. .
  • Examples of the form of the reinforcing fibers include so-called tow sheets in which high-strength, high-modulus fibers are arranged in one direction, unidirectional or bidirectional fabrics in which the fiber threads are arranged in one or two directions, Examples include triaxial woven fabrics arranged in three directions and multiaxial woven fabrics arranged in multiple directions.
  • the fibers are preferably arranged so as to secure an appropriate gap between the strands in order to improve the resin impregnation property of the base material.
  • the method for molding fiber-reinforced plastics using the resin composition for fiber-reinforced plastics of the present invention is not particularly limited, but examples thereof include extrusion molding, blow molding, compression molding, and vacuum molding. , injection molding, RTM (resin transfer molding) molding, VaRTM (vacuum assist resin transfer molding) molding, laminate molding, hand lay-up molding, filament winding molding, and the like.
  • the amount of the cured product of the resin composition for fiber-reinforced plastic contained in the fiber-reinforced plastic is preferably 5 to 95% by mass, particularly preferably 10 to 80% by mass, further preferably 20 to 70% by mass. It is preferable because it can exhibit excellent physical properties by being used in.
  • the fiber-reinforced plastic obtained using the resin composition for fiber-reinforced plastic of the present invention can be used for various purposes.
  • general industrial applications such as structural materials for moving bodies such as automobiles, ships and railway vehicles, drive shafts, leaf springs, windmill blades, pressure vessels, flywheels, papermaking rollers, roofing materials, cables, and repair and reinforcement materials;
  • Aerospace applications such as fuselages, main wings, tail wings, rotor blades, fairings, cowls, doors, seats, interior materials, motor cases, antennas; golf shafts, fishing rods, tennis and badminton rackets, hockey sticks, and so on.
  • Sports applications such as ski pole applications.
  • Example 1 In a 500 mL disposable cup, 98.6 g of ADEKA RESIN EP-4100E (manufactured by ADEKA Co., Ltd.; bisphenol A type epoxy resin, epoxy equivalent: 190 g / eq.), 32 g of Jeffamine D-230 (manufactured by Huntsman; polypropylene polyamine) , 2 g of hishicolin PX-4ET (manufactured by Nippon Kagaku Kogyo; tetrabutylphosphonium O,O-diethylphosphorodithioate) and KBM-403 (manufactured by Shin-Etsu Chemical Co., Ltd., ⁇ -glycidoxypropyltrimethoxysilane) 1.4 g was added and stirred with a spatula for 5 minutes at 25°C. Thereafter, the mixture was further stirred using a planetary stirrer to obtain a resin composition.
  • ADEKA RESIN EP-4100E manufactured by
  • Example 2 In a 500 mL disposable cup, 83.9 g of ADEKA RESIN EP-4100E (manufactured by ADEKA Corporation; bisphenol A type epoxy resin, epoxy equivalent: 190 g / eq.), ADEKA GLYCIROL ED-523T (manufactured by ADEKA Corporation; neopentyl Glycol-type epoxy resin: 14.8 g of epoxy equivalent 140 g / eq.), 32 g of Jeffamine D-230 (manufactured by Huntsman; polypropylene polyamine), Hishikorin PX-4ET (manufactured by Nippon Kagaku Kogyo; tetrabutylphosphonium O, O- 2 g of diethyl phosphorodithioate) and 1.3 g of KBM-403 (manufactured by Shin-Etsu Chemical Co., Ltd., ⁇ -glycidoxypropyltrimethoxysilane) were added and
  • Example 3 79.0 g of ADEKA RESIN EP-4100E (manufactured by ADEKA Corporation; bisphenol A type epoxy resin, epoxy equivalent: 190 g/eq.) and 30 of Jeffamine D-230 (manufactured by Huntsman; polypropylene polyamine) are placed in a 500 mL disposable cup.
  • Example 4 In a 500 mL disposable cup, 74.0 g of ADEKA RESIN EP-4100E (manufactured by ADEKA Co., Ltd.; bisphenol A type epoxy resin, epoxy equivalent: 190 g / eq.), 30 of Jeffamine D-230 (manufactured by Huntsman; polypropylene polyamine) 6 g, Hishikorin PX-4ET (manufactured by Nippon Kagaku Kogyo; tetrabutylphosphonium O,O-diethylphosphorodithioate) 2 g, KBM-403 (manufactured by Shin-Etsu Chemical Co., Ltd., ⁇ -glycidoxypropyltrimethoxysilane ) and 24.8 g of ADEKA GLYCIROL ED-509E (manufactured by ADEKA; t-butylphenylglycidyl ether: epoxy equivalent: 210 g/eq.) were
  • the resin composition for fiber-reinforced plastics of the present invention has excellent curability, and the fiber-reinforced plastic obtained using it has excellent non-coloring properties.
  • the resin composition for fiber-reinforced plastics of the present invention can provide fiber-reinforced plastics with excellent curability and excellent non-coloring properties, it is possible to provide molded articles with excellent appearance.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Materials Engineering (AREA)
  • Epoxy Resins (AREA)

Abstract

Le but de la présente invention est de fournir une composition de résine pour des matières plastiques renforcées par des fibres qui est appropriée pour améliorer la résistance de matières plastiques renforcées par des fibres, présente un excellent équilibre entre la durée de vie en pot et l'aptitude au durcissement, et présente d'excellentes propriétés de non-coloration.　Cette composition de résine comprend un composant (A), qui est une résine époxyde, un composant (B), qui est une polyoxyalkylène-polyamine, et un composant (C), qui est au moins un composé choisi parmi les composés représentés par la formule (1). (Dans la formule (1), R1 à R6 représentent chacun indépendamment un groupe hydrocarboné en C1-C10 et X1 à X4 représentent chacun indépendamment un atome d'oxygène ou un atome de soufre.)
PCT/JP2023/004329 2022-02-16 2023-02-09 Composition de résine pour matière plastique renforcée par des fibres, et matière plastique renforcée par des fibres WO2023157750A1 (fr)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5847015A (ja) * 1981-09-14 1983-03-18 Mitsui Tekisako Chem Kk エポキシ樹脂用硬化剤
JP2001151862A (ja) * 1999-11-22 2001-06-05 Tosoh Corp エポキシ樹脂組成物
JP2008266541A (ja) * 2007-04-25 2008-11-06 Sanyo Chem Ind Ltd エポキシ樹脂用硬化剤
WO2019013025A1 (fr) * 2017-07-13 2019-01-17 東レ株式会社 Article moulé, et procédé de fabrication de celui-ci
JP2021088639A (ja) * 2019-12-03 2021-06-10 株式会社Adeka 樹脂組成物、その硬化物、繊維強化プラスチック及び繊維強化プラスチックの難燃化方法

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5847015A (ja) * 1981-09-14 1983-03-18 Mitsui Tekisako Chem Kk エポキシ樹脂用硬化剤
JP2001151862A (ja) * 1999-11-22 2001-06-05 Tosoh Corp エポキシ樹脂組成物
JP2008266541A (ja) * 2007-04-25 2008-11-06 Sanyo Chem Ind Ltd エポキシ樹脂用硬化剤
WO2019013025A1 (fr) * 2017-07-13 2019-01-17 東レ株式会社 Article moulé, et procédé de fabrication de celui-ci
JP2021088639A (ja) * 2019-12-03 2021-06-10 株式会社Adeka 樹脂組成物、その硬化物、繊維強化プラスチック及び繊維強化プラスチックの難燃化方法

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