WO2012161100A1 - Composition de résine méthacrylique et produit moulé à base de celle-ci - Google Patents

Composition de résine méthacrylique et produit moulé à base de celle-ci Download PDF

Info

Publication number
WO2012161100A1
WO2012161100A1 PCT/JP2012/062714 JP2012062714W WO2012161100A1 WO 2012161100 A1 WO2012161100 A1 WO 2012161100A1 JP 2012062714 W JP2012062714 W JP 2012062714W WO 2012161100 A1 WO2012161100 A1 WO 2012161100A1
Authority
WO
WIPO (PCT)
Prior art keywords
resin composition
methacrylic
methacrylic acid
mass
ester compound
Prior art date
Application number
PCT/JP2012/062714
Other languages
English (en)
Japanese (ja)
Inventor
智子 小倉
善光 生駒
斉藤　英一郎
Original Assignee
パナソニック株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by パナソニック株式会社 filed Critical パナソニック株式会社
Priority to JP2013516334A priority Critical patent/JPWO2012161100A1/ja
Priority to CN201280023692.0A priority patent/CN103534284A/zh
Publication of WO2012161100A1 publication Critical patent/WO2012161100A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1811—C10or C11-(Meth)acrylate, e.g. isodecyl (meth)acrylate, isobornyl (meth)acrylate or 2-naphthyl (meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/04—Acids; Metal salts or ammonium salts thereof
    • C08F220/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/10—Esters
    • C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
    • C08F222/103—Esters of polyhydric alcohols or polyhydric phenols of trialcohols, e.g. trimethylolpropane tri(meth)acrylate

Definitions

  • the present invention relates to a methacrylic resin composition and a molded body thereof, and in particular, can be suitably used as a substitute for a glass plate such as a window glass for vehicles or a building, a cover of a solar cell panel, and the like. is there.
  • Methacrylic acid ester compounds are used as various molding materials taking advantage of properties such as transparency, weather resistance, and surface hardness (see, for example, Patent Document 1).
  • the methacrylic ester compound has a large cure shrinkage and is difficult to mold. That is, the reaction of the vinyl group existing in the molecular chain occurs in the methacrylic acid ester compound.
  • the intermolecular distance (0.3 to 0.6 nm) between the vinyl groups existing before the reaction changes to a single bond (0.14 nm) by the reaction, so that the reaction causes contraction. .
  • the present invention has been made in view of the above points, and provides a methacrylic resin composition capable of reducing curing shrinkage while maintaining heat resistance and transparency, and a molded body using the same. It is intended.
  • the methacrylic resin composition according to the present invention includes a methacrylic acid ester compound containing at least one cyclic methacrylic acid ester, a polyfunctional unsaturated ester compound, and a radical polymerization start having a 10-hour half-life temperature of 50 to 100 ° C. It is characterized by containing an agent.
  • the ratio of the cyclic methacrylic acid ester is preferably 5 to 40% by mass of the methacrylic acid ester compound.
  • methacrylic resin composition of the present invention it is preferable to dissolve and contain an acrylic resin or a methacrylic resin.
  • the acrylic acid derivative or methacrylic acid derivative having a hindered topepyridine skeleton is preferably contained in an amount of 0.1 to 10% with respect to the total amount of the methacrylic ester compound.
  • the acrylic acid derivative or methacrylic acid derivative having a functional group that absorbs ultraviolet rays in the skeleton is contained in an amount of 0.1 to 10% with respect to the total amount of the methacrylic ester compound. It is preferable.
  • the molded body according to the present invention is formed by molding the methacrylic resin composition.
  • the molded product of the present invention preferably contains 5 to 40% by mass of the cyclic methacrylate.
  • the methacrylic resin composition and molded product thereof according to the present invention can reduce curing shrinkage while maintaining heat resistance and transparency.
  • the methacrylic resin composition according to the present invention is a radical polymerization initiator having a methacrylic acid ester compound containing at least one cyclic methacrylic acid ester, a polyfunctional unsaturated ester compound, and a 10-hour half-life temperature of 50 ° C. to 100 ° C. Containing the agent. Moreover, you may contain an acrylic resin as needed.
  • cyclic methacrylate examples include cyclohexyl methacrylate, phenoxy methacrylate, 4-t-butylcyclohexyl methacrylate, phenoxypolyethylene glycol methacrylate, dicyclopentenyloxyethyl methacrylate, tricyclodecyl methacrylate, phenoxyethyl methacrylate, benzyl methacrylate, adamantyl methacrylate.
  • Oxetane methacrylate, ⁇ -butyl lactone methacrylate, isobornyl methacrylate, dicyclopentenyl methacrylate, tetrahydrofurfuryl methacrylate, and the like can be used. These may be used alone or in combination of two or more.
  • Such a cyclic methacrylic acid ester is particularly preferably contained in an amount of 5 to 40% by mass based on the total amount of the methacrylic acid ester compound. Curing shrinkage at the time of shaping
  • molding of a methacrylic-type resin composition can be reduced as content of cyclic methacrylate is this range.
  • methacrylic acid ester used in addition to the cyclic methacrylic acid ester as described above include, for example, methyl methacrylate, ethyl methacrylate, butyl methacrylate, isobutyl methacrylate, 2-ethylhexyl methacrylate, lauryl methacrylate, propyl methacrylate.
  • Isopropyl methacrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl methacrylate, 3-hydroxypropyl methacrylate, and the like can be used. These may be used alone or in combination of two or more.
  • polyfunctional unsaturated ester compound examples include divinylbenzene ethylene glycol dimethacrylate, divinylbenzene ethylene glycol diacrylate, ethylene glycol dimethacrylate, ethylene glycol acrylate, diethylene glycol dimethacrylate, diethylene glycol diacrylate, triethylene glycol dimethacrylate, Ethylene glycol diacrylate, polyethylene glycol dimethacrylate, polyethylene glycol acrylate, 1,3-butylene glycol dimethacrylate, 1,3-propylene glycol dimethacrylate, 1,4-butylene glycol dimethacrylate, polypropylene glycol dimethacrylate, 1,6- Hexanediol dimethacrylate, Bifunctional unsaturated esters such as opentyl glycol dimethacrylate, trimethylol ethane trimethacrylate, trimethylol ethane triacrylate, trimethylol propane trimethacrylate, trimethylol propane triacrylate, methyl
  • a tetrafunctional unsaturated ester such as a trifunctional unsaturated ester, tetramethylolmethane tetramethacrylate, tetramethylolmethane tetraacrylate, dipropylene glycol dimethacrylate, or dipropylene glycol diacrylate can be used. These may be used alone or in combination of two or more.
  • diacyl peroxides As the radical polymerization initiator having a 10 hour half-life temperature of 50 to 100 ° C., diacyl peroxides, peroxyketals, alkyl peresters, and percarbonates can be used.
  • the 10-hour half-life temperature of the radical polymerization initiator is in the above range since insufficient curing and foaming can be suppressed.
  • the (meth) acrylic resin can be dissolved and blended as necessary.
  • “(Meth) acryl” refers to methacryl or acryl. By blending this (meth) acrylic resin, viscosity adjustment and improvement of moldability can be expected.
  • the (meth) acrylic resin used in the present invention include homopolymers or copolymers obtained from alkyl acrylates such as methyl acrylate, ethyl acrylate and butyl acrylate and / or alkyl methacrylates such as methyl methacrylate, ethyl methacrylate and butyl methacrylate.
  • a polymer can be used.
  • a copolymer of these monomers and other copolymerizable monomers can also be used.
  • polymethyl methacrylate polymethyl methacrylate (PMMA)
  • PMMA polymethyl methacrylate
  • the acrylic resin is preferably 10 to 30% by mass of the methacrylic ester compound.
  • the acrylic resin can be produced by a general polymerization technique such as solution polymerization, emulsion polymerization, suspension polymerization, and the production method is not particularly limited.
  • an acrylic acid derivative or a methacrylic acid derivative having a hindered topepyridine skeleton can be blended as necessary.
  • an improvement in light resistance can be expected. This is because the hindered topepyridine skeleton has an effect of capturing radicals generated by light (particularly ultraviolet rays) and inactivating them.
  • acrylic acid derivatives or methacrylic acid derivatives having a hindered topepyridine skeleton used in the present invention include 1,2,2,6,6-pentamethyl-4-piperidyl methacrylate (for example, ADK STAB LA manufactured by ADEKA Corporation). -82), 2,2,6,6-tetramethyl-4-piperidyl methacrylate (for example, ADK STAB LA-87 manufactured by ADEKA Corporation) and the like.
  • the acrylic acid derivative or methacrylic acid derivative having such a hindered topepyridine skeleton preferably has a content of 0.1 to 10% by mass, particularly 1 to 3% by mass, based on the total amount of the methacrylic acid ester compound. It is preferable that it is a content rate.
  • the content of the acrylic acid derivative or methacrylic acid derivative having a hindered topepyridine skeleton is 0.1 to 10% by mass, the weather resistance can be improved without impairing the moldability of the methacrylic resin composition.
  • an acrylic acid derivative or a methacrylic acid derivative having a functional group that absorbs ultraviolet rays in the skeleton can be blended as necessary.
  • an improvement in weather resistance can be expected. This is because if a functional group that absorbs ultraviolet rays is added to the methacrylic acid ester polymer by polymerization, the ultraviolet rays can be absorbed on the surface or inside of the resin of the molded article while maintaining the properties of the acrylic resin. In other words, when it has ultraviolet absorbing ability, it is possible to suppress generation of radicals due to ultraviolet rays on the resin surface or inside of the molded body.
  • acrylic acid derivative or methacrylic acid derivative having a functional group that absorbs ultraviolet rays in the skeleton used in the present invention 1- (2-benzotriazole) -2-hydroxy-5- (2-methacryloyloxyethyl) benzene or this Similar compounds are mentioned.
  • Such an acrylic acid derivative or methacrylic acid derivative having a functional group that absorbs ultraviolet rays in the skeleton preferably has a content of 0.1 to 10% by mass, particularly 1 to 1%, based on the total amount of the methacrylic acid ester compound.
  • the content is preferably 3% by mass.
  • the methacrylic resin composition may contain an inorganic ultraviolet shielding agent such as titanium oxide, zinc oxide, cerium oxide or the like, as long as the transparency is not impaired, and other light stabilizers, antioxidants, heat A stabilizer, an antistatic agent, a heat ray reflective agent, a heat ray absorbent, a flame retardant, a lubricant, a pigment, a filler, and the like may be included.
  • an inorganic ultraviolet shielding agent such as titanium oxide, zinc oxide, cerium oxide or the like, as long as the transparency is not impaired, and other light stabilizers, antioxidants, heat A stabilizer, an antistatic agent, a heat ray reflective agent, a heat ray absorbent, a flame retardant, a lubricant, a pigment, a filler, and the like may be included.
  • the methacrylic resin composition of the present invention is prepared by blending a methacrylic acid ester compound, a polyfunctional unsaturated ester compound, and a radical polymerization initiator having a 10-hour half-life temperature of 50 ° C. to 100 ° C. be able to.
  • the blending ratio of each component is 0.5 to 20 parts by mass of the polyfunctional unsaturated ester compound and 50 hours to 100 ° C. of 10 hours half-life temperature with respect to 100 parts by mass of the methacrylic ester compound.
  • the radical polymerization initiator can be 0.1 to 5 parts by mass.
  • the molded body of the present invention can be obtained by injecting the above methacrylic resin composition into a mold such as a mold, a resin mold, or a glass mold and curing it in a specific temperature range under pressure or normal pressure. .
  • a methacrylic resin composition can be applied onto the above mold to obtain a film-like molded body.
  • a methacrylic resin composition containing a methacrylic acid ester compound containing at least one cyclic methacrylic acid ester, the polyfunctional unsaturated ester compound, and the radical polymerization initiator is described. It can be poured into a mold and cured by heating to obtain a molded product. At this time, the heat curing temperature is preferably in the range of 50 ° C.
  • the heat curing temperature is 50 ° C. or higher and lower than 100 ° C., a molded article having excellent heat resistance and transparency and less curing shrinkage can be obtained.
  • the methacrylic resin composition contains a cyclic methacrylic ester, it is excellent in heat resistance and transparency, and cure shrinkage is reduced.
  • a methacrylic resin molded article may be used for any application as long as the transparency and weather resistance are effectively used, and may be a film or sheet of about 30 ⁇ m to 1 mm. Good.
  • the methacrylic resin composition can be suitably used as described above for forming a thick article (thickness 1 to 10 mm).
  • a methacrylic resin composition as described above When a methacrylic resin composition as described above is molded, a polyfunctional unsaturated ester compound becomes a crosslinking point, and a molded product having a three-dimensional crosslinked structure can be obtained. Since this molded article has a three-dimensional crosslinked structure, it is superior in heat resistance to a molded article made of a methacrylic resin composition not having a three-dimensional crosslinked structure. Moreover, it is excellent in transparency, which is a feature of methacrylic acid ester.
  • Example 1 90 parts by mass of methyl methacrylate [Chemical Formula 1], 10 parts by mass of isobornyl methacrylate [Chemical Formula 2] as a cyclic methacrylate, and 1 part by mass of trimethylolpropane trimethacrylate [Chemical Formula 3] as a polyfunctional unsaturated ester compound Then, 0.3 part by mass of di- (3,5,5-trimethylhexanoyl) peroxide as a radical polymerization initiator was mixed to obtain a methacrylic resin composition. As the radical polymerization initiator, Trigonox 36-C75 manufactured by Kayaku Akzo Co., Ltd. was used. Next, the methacrylic resin composition thus prepared was poured into a mold and cured at 75 ° C. for 1 hour to obtain a molded body.
  • the radical polymerization initiator Trigonox 36-C75 manufactured by Kayaku Akzo Co., Ltd. was used.
  • Example 2 Molding was performed in the same manner as in Example 1 except that the blending ratio of methyl methacrylate and cyclic methacrylate was changed.
  • Example 5 Comparative Example 3 Molding was performed in the same manner as in Example 1 except that the type of radical polymerization initiator was changed.
  • Example 3 75 parts by mass of methyl methacrylate [Chemical Formula 1], 10 parts by mass of isobornyl methacrylate [Chemical Formula 2] as a cyclic methacrylate, 15 parts by mass of polymethyl methacrylate, and trimethylolpropanetri as a polyfunctional unsaturated ester compound 1 part by weight of methacrylate [Chemical Formula 3] and 0.3 part by weight of di- (3,5,5-trimethylhexanoyl) peroxide as a radical polymerization initiator were mixed to obtain a methacrylic resin composition.
  • the radical polymerization initiator Trigonox 36-C75 manufactured by Kayaku Akzo Co., Ltd. was used.
  • the methacrylic resin composition thus prepared was poured into a mold and cured at 75 ° C. for 1 hour to obtain a molded body.
  • Example 4 Molding was performed in the same manner as in Example 3 except that the blending ratio of methyl methacrylate and polymethyl methacrylate was changed.
  • Example 8 100 parts by mass of isobornyl methacrylate [Chemical Formula 2] as a cyclic methacrylate, 1 part by mass of trimethylolpropane trimethacrylate [Chemical Formula 3] as a polyfunctional unsaturated ester compound, and di- (3,5 as a radical polymerization initiator , 5-trimethylhexanoyl) peroxide 0.3 parts by mass was mixed to obtain a methacrylic resin composition.
  • the radical polymerization initiator Trigonox 36-C75 manufactured by Kayaku Akzo Co., Ltd. was used.
  • the methacrylic resin composition thus prepared was poured into a mold and cured at 75 ° C. for 1 hour to obtain a molded body.
  • Example 9 90 parts by mass of methyl methacrylate [Chemical Formula 1], 10 parts by mass of isobornyl methacrylate [Chemical Formula 2] as a cyclic methacrylic acid ester, and 1,2 methacrylic acid as an acrylic acid derivative or methacrylic acid derivative having a hindered topepyridine skeleton 1,6,6-pentamethyl-4-piperidyl [Chemical Formula 4] 1 part by mass, polyfunctional unsaturated ester compound trimethylolpropane trimethacrylate [Chemical Formula 3] 1 part by mass, radical polymerization initiator di- (3 , 5,5-trimethylhexanoyl) peroxide 0.3 parts by mass was mixed to obtain a methacrylic resin composition.
  • Trigonox 36-C75 of Kayaku Akzo Co., Ltd. was used as the radical polymerization initiator, and ADK STAB LA-82 manufactured by ADEKA Co., Ltd. was used as the acrylic acid derivative or methacrylic acid derivative having a hindered topepyridine skeleton. .
  • the methacrylic resin composition thus prepared was poured into a mold and cured at 75 ° C. for 1 hour to obtain a molded body.
  • Example 10 Molding was carried out in the same manner as in Example 9 except that the blending ratio of methyl methacrylate and a methacrylic acid derivative having a hindered topepyridine skeleton was changed.
  • Example 12 90 parts by mass of methyl methacrylate [Chemical Formula 1], 10 parts by mass of isobornyl methacrylate [Chemical Formula 2] as a cyclic methacrylic ester, and 1-acrylic acid derivative or methacrylic acid derivative having a functional group that absorbs ultraviolet rays in the skeleton.
  • the radical polymerization initiator is Trigonox 36-C75 of Kayaku Akzo Co., Ltd.
  • the acrylic acid derivative or methacrylic acid derivative having a functional group that absorbs ultraviolet rays as a skeleton is RUVA-93 manufactured by Otsuka Chemical Co., Ltd.
  • the methacrylic resin composition thus prepared was poured into a mold and cured at 75 ° C. for 1 hour to obtain a molded body.
  • Example 13 Molding was carried out in the same manner as in Example 12 except that the blending ratio of methyl methacrylate and a methallylic acid derivative having a functional group that absorbs ultraviolet rays in the skeleton was changed.
  • Example 15 90 parts by mass of methyl methacrylate [Chemical Formula 1], 10 parts by mass of isobornyl methacrylate [Chemical Formula 2] as a cyclic methacrylic acid ester, and 1,2 methacrylic acid as an acrylic acid derivative or methacrylic acid derivative having a hindered topepyridine skeleton 1 part of 2,6,6-pentamethyl-4-piperidyl [Chemical Formula 4] and 1- (2-benzotriazole) -2-hydroxy as an acrylic acid derivative or methacrylic acid derivative having a functional group that absorbs ultraviolet rays in the skeleton 1 part by mass of -5- (2-methacryloyloxyethyl) benzene [Chemical Formula 5], 1 part by mass of trimethylolpropane trimethacrylate [Chemical Formula 3] as a polyfunctional unsaturated ester compound, and di- (3 , 5,5-trimethylhexanoyl) peroxide 0.3 parts by mass,
  • the radical polymerization initiator is Trigonox 36-C75 manufactured by Kayaku Akzo Co., Ltd.
  • the acrylic acid derivative or methacrylic acid derivative having a hindered topepyridine skeleton is ADK STAB LA-82 manufactured by ADEKA Co., Ltd. RUVA-93 manufactured by Otsuka Chemical Co., Ltd. was used as an acrylic acid derivative or a methacrylic acid derivative having a functional group that absorbs.
  • the methacrylic resin composition thus prepared was poured into a mold and cured at 75 ° C. for 1 hour to obtain a molded body.
  • the weather resistance test was conducted using DPWL-5R manufactured by Suga Test Instruments. The test conditions were based on JIS A 1415 and JIS K 7350-3. After six samples were installed in a dew panel weather meter, the black panel temperature was set to 63 ° C (during irradiation), the irradiance was set to 30 W / m 2 (300 to 400 nm), irradiation for 4 hours, and extinction (condensation) for 4 hours. The test cycle was 200 hours. As an evaluation method, a white plate was placed on the back surface of the resin and measured with a color difference meter, and the change in color before and after the test was shown as a ⁇ E value.
  • Examples 1 to 8 have the same transparency, excellent heat resistance, and suppressed curing shrinkage, as compared with Comparative Examples 1 and 2.
  • the weather resistance is further excellent. From this, when a cyclic methacrylic ester is blended with a methacrylic resin composition, curing shrinkage can be reduced while maintaining heat resistance and transparency. Furthermore, when one or both of the hindered piperidine skeleton and the functional group that absorbs ultraviolet rays are included in the skeleton, the weather resistance of the molded article can be improved. it can.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

La présente invention a pour but de pourvoir à une composition de résine méthacrylique par laquelle l'apparition d'un retrait lors d'un durcissement peut être réduite tout en maintenant une résistance à la chaleur et une transparence. Cette composition de résine méthacrylique comprend un composé ester d'acide méthacrylique comprenant au moins un ester d'acide méthacrylique cyclique, un composé ester insaturé polyfonctionnel et un amorceur de polymérisation radicalaire ayant une température de demi-vie de 10 heures de 50-100 °C.
PCT/JP2012/062714 2011-05-23 2012-05-17 Composition de résine méthacrylique et produit moulé à base de celle-ci WO2012161100A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP2013516334A JPWO2012161100A1 (ja) 2011-05-23 2012-05-17 成形用メタクリル系樹脂組成物及びその成形体
CN201280023692.0A CN103534284A (zh) 2011-05-23 2012-05-17 甲基丙烯酸系树脂组合物及其成型体

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP2011-114867 2011-05-23
JP2011114867 2011-05-23
JP2011-228992 2011-10-18
JP2011228992 2011-10-18

Publications (1)

Publication Number Publication Date
WO2012161100A1 true WO2012161100A1 (fr) 2012-11-29

Family

ID=47217179

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2012/062714 WO2012161100A1 (fr) 2011-05-23 2012-05-17 Composition de résine méthacrylique et produit moulé à base de celle-ci

Country Status (3)

Country Link
JP (1) JPWO2012161100A1 (fr)
CN (1) CN103534284A (fr)
WO (1) WO2012161100A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016063898A1 (fr) * 2014-10-21 2016-04-28 三菱レイヨン株式会社 Composition de résine (méth)acrylique et objet moulé en résine
JP2020105492A (ja) * 2018-12-26 2020-07-09 東洋インキＳｃホールディングス株式会社 紫外線吸収性単量体、アクリル重合体、樹脂組成物および成形体
WO2020171071A1 (fr) * 2019-02-20 2020-08-27 東洋インキＳｃホールディングス株式会社 Polymère absorbant les rayons ultraviolets, composition de résine de moulage et corps moulé

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP6301526B1 (ja) * 2017-03-29 2018-03-28 シプロ化成株式会社 ベンゾトリアゾール誘導体化合物およびその用途
CN107856468B (zh) * 2017-11-30 2019-07-12 江阴市新城东天工专业设计工作室 一种观赏石底座及其制作方法

Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6183213A (ja) * 1984-09-29 1986-04-26 Kyowa Gas Chem Ind Co Ltd デイスク基板とその製造方法
JPS62232414A (ja) * 1986-04-01 1987-10-12 Hitachi Chem Co Ltd 注型用光学樹脂材料
JPH02133415A (ja) * 1988-11-14 1990-05-22 Hitachi Chem Co Ltd 高屈折率プラスチックレンズの製造方法
JPH10130331A (ja) * 1996-10-28 1998-05-19 Kureha Chem Ind Co Ltd 固体撮像素子パッケージ用プラスチック製リッド材およびその製造方法
JP2000264929A (ja) * 1999-03-17 2000-09-26 Hitachi Chem Co Ltd 光学用共重合体、光学用共重合体の製造方法、及び光学用部品
JP2004156025A (ja) * 2002-10-17 2004-06-03 Nippon Shokubai Co Ltd 水性樹脂分散体、水性樹脂組成物および水性樹脂組成物の製造方法
JP2004224891A (ja) * 2003-01-22 2004-08-12 Mitsubishi Rayon Co Ltd アクリル系樹脂、樹脂板およびその製造方法
WO2004108778A1 (fr) * 2003-06-09 2004-12-16 Mitsui Chemicals, Inc. Composition de resine methacrylique reticulable et element transparent
JP2007262414A (ja) * 1998-10-29 2007-10-11 Advanced Medical Optics Inc ポリマー組成物および眼用レンズ本体
WO2009005036A1 (fr) * 2007-07-02 2009-01-08 Idemitsu Kosan Co., Ltd. Résine pour composant optique, composition de matière première utilisée pour la résine pour composant optique et composant optique

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6183213A (ja) * 1984-09-29 1986-04-26 Kyowa Gas Chem Ind Co Ltd デイスク基板とその製造方法
JPS62232414A (ja) * 1986-04-01 1987-10-12 Hitachi Chem Co Ltd 注型用光学樹脂材料
JPH02133415A (ja) * 1988-11-14 1990-05-22 Hitachi Chem Co Ltd 高屈折率プラスチックレンズの製造方法
JPH10130331A (ja) * 1996-10-28 1998-05-19 Kureha Chem Ind Co Ltd 固体撮像素子パッケージ用プラスチック製リッド材およびその製造方法
JP2007262414A (ja) * 1998-10-29 2007-10-11 Advanced Medical Optics Inc ポリマー組成物および眼用レンズ本体
JP2000264929A (ja) * 1999-03-17 2000-09-26 Hitachi Chem Co Ltd 光学用共重合体、光学用共重合体の製造方法、及び光学用部品
JP2004156025A (ja) * 2002-10-17 2004-06-03 Nippon Shokubai Co Ltd 水性樹脂分散体、水性樹脂組成物および水性樹脂組成物の製造方法
JP2004224891A (ja) * 2003-01-22 2004-08-12 Mitsubishi Rayon Co Ltd アクリル系樹脂、樹脂板およびその製造方法
WO2004108778A1 (fr) * 2003-06-09 2004-12-16 Mitsui Chemicals, Inc. Composition de resine methacrylique reticulable et element transparent
WO2009005036A1 (fr) * 2007-07-02 2009-01-08 Idemitsu Kosan Co., Ltd. Résine pour composant optique, composition de matière première utilisée pour la résine pour composant optique et composant optique

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016063898A1 (fr) * 2014-10-21 2016-04-28 三菱レイヨン株式会社 Composition de résine (méth)acrylique et objet moulé en résine
JPWO2016063898A1 (ja) * 2014-10-21 2017-08-10 三菱ケミカル株式会社 （メタ）アクリル樹脂組成物及び樹脂成形体
US10428213B2 (en) 2014-10-21 2019-10-01 Mitsubishi Chemical Corporation (Meth)acrylic resin composition and resin molded article
JP2020105492A (ja) * 2018-12-26 2020-07-09 東洋インキＳｃホールディングス株式会社 紫外線吸収性単量体、アクリル重合体、樹脂組成物および成形体
JP7476520B2 (ja) 2018-12-26 2024-05-01 ａｒｔｉｅｎｃｅ株式会社 紫外線吸収性単量体、アクリル重合体、樹脂組成物および成形体
WO2020171071A1 (fr) * 2019-02-20 2020-08-27 東洋インキＳｃホールディングス株式会社 Polymère absorbant les rayons ultraviolets, composition de résine de moulage et corps moulé
CN113454132A (zh) * 2019-02-20 2021-09-28 东洋油墨Sc控股株式会社 紫外线吸收性聚合物、成形用树脂组合物及成形体

Also Published As

Publication number Publication date
CN103534284A (zh) 2014-01-22
JPWO2012161100A1 (ja) 2014-07-31

Similar Documents

Publication Publication Date Title
JP6752951B2 (ja) 紫外線吸収基を有するオリゴマーを含むフルオロポリマー組成物
EP3161078B1 (fr) Film extrudé comprenant une composition de polymère fluoré comprenant au moins un oligomère
WO2012161100A1 (fr) Composition de résine méthacrylique et produit moulé à base de celle-ci
JP5587869B2 (ja) 硬化性組成物及びその硬化物
JP2013241515A (ja) 硬化性組成物およびその硬化物
KR20060048323A (ko) 수지 조성물
JP2012067174A (ja) 架橋性樹脂組成物、およびそれを含む封止剤
TW201137021A (en) Composition for a low-refractive-index film
JPWO2016181742A1 (ja) ラジカル硬化性組成物およびその硬化物
JP6404585B2 (ja) ラジカル硬化性組成物およびその硬化物
US20140243493A1 (en) (meth) acrylate resin composition and cured product of same
WO2021079886A1 (fr) Feuille de résine et procédé pour la production de celle-ci
JP2013018827A (ja) 硬化性組成物およびその硬化物
JP2015517014A (ja) ポリカーボネート配合物製品およびその製造方法
TWI632180B (zh) Composition for reflective material and optical semiconductor light-emitting device using the same
CA2720385A1 (fr) Matiere polymerisable comprenant des nanoparticules reticulantes
JP2014000802A (ja) 透明積層体及びその製造方法
JPH0129217B2 (fr)
JP2018135481A (ja) 硬化性組成物及び膜
JP2020094193A (ja) メタクリル系樹脂組成物及び樹脂成形体
JP2007152962A (ja) 紫外線吸収性複合フィルム
JP2016003277A (ja) 波長変換材料
JP2021070729A (ja) 樹脂組成物及び成形体
WO2015194593A1 (fr) Matériau de conversion de longueur d'onde
TWI845944B (zh) 單體組成物、甲基丙烯酸系樹脂組成物及樹脂成形體

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 12790250

Country of ref document: EP

Kind code of ref document: A1

DPE1 Request for preliminary examination filed after expiration of 19th month from priority date (pct application filed from 20040101)
ENP Entry into the national phase

Ref document number: 2013516334

Country of ref document: JP

Kind code of ref document: A

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 12790250

Country of ref document: EP

Kind code of ref document: A1