WO2016181784A1 - Résine de (méth)acrylate et élément optique - Google Patents

Résine de (méth)acrylate et élément optique Download PDF

Info

Publication number
WO2016181784A1
WO2016181784A1 PCT/JP2016/062613 JP2016062613W WO2016181784A1 WO 2016181784 A1 WO2016181784 A1 WO 2016181784A1 JP 2016062613 W JP2016062613 W JP 2016062613W WO 2016181784 A1 WO2016181784 A1 WO 2016181784A1
Authority
WO
WIPO (PCT)
Prior art keywords
meth
acrylate
group
resin
acrylate resin
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/JP2016/062613
Other languages
English (en)
Japanese (ja)
Inventor
駿介 山田
厳 服部
義信 出口
亀山　裕史
伸生 小林
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
DIC Corp
Original Assignee
DIC Corp
Dainippon Ink and Chemicals Co Ltd
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 DIC Corp, Dainippon Ink and Chemicals Co Ltd filed Critical DIC Corp
Priority to JP2016560023A priority Critical patent/JP6168241B2/ja
Priority to CN201680027788.2A priority patent/CN107531831A/zh
Publication of WO2016181784A1 publication Critical patent/WO2016181784A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Images

Classifications

    • 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
    • C08F20/00—Homopolymers and 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
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/10—Esters
    • C08F20/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F20/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety

Definitions

  • the present invention relates to a (meth) acrylate resin excellent in heat resistance, moisture absorption resistance and yellowing resistance in a cured product, a photocurable composition containing the same, a cured product thereof, and an optical member.
  • On-chip lenses mounted on image sensors such as CCDs and CMOSs have been widely used that are manufactured by a melt method in which a dot pattern is applied to a thermoplastic resin, and this is formed into a spherical lens shape by heat flow.
  • a melt method in which a dot pattern is applied to a thermoplastic resin, and this is formed into a spherical lens shape by heat flow.
  • spherical lenses have large chromatic aberration, there is a limit to high definition and high sensitivity.
  • a shape transfer method in which a photocurable resin is shaped by an aspherical lens shape mold has been proposed.
  • the photo-curable resin is made of a resin or monomer having a photopolymerizable group such as a (meth) acryloyl group, and can be reduced in viscosity by containing many low molecular weight components. .
  • heat resistance and moisture resistance are not sufficient for use in on-chip lens applications, and yellowing and deformation are likely to occur.
  • a photocurable resin excellent in moisture absorption resistance and the like for example, a photocurable resin obtained by reacting a bisphenol A type epoxy resin and methacrylic anhydride is known (see Patent Document 1). Although such a resin with a high aromatic ring content exhibits relatively high heat resistance, it is not sufficient in both heat resistance and moisture resistance for use in on-chip lens applications, and is likely to cause yellowing and deformation. It was.
  • the problem to be solved by the present invention is a (meth) acrylate resin excellent in heat resistance, moisture absorption resistance and yellowing resistance in a cured product, a photocurable composition containing the resin, a cured product thereof, and an optical member Is to provide.
  • a methacrylate resin obtained by reacting an aromatic diglycidyl ether compound with (meth) acrylic acid and methacrylic anhydride is a cured product.
  • the present invention has been found to be excellent in heat resistance, moisture absorption resistance and yellowing resistance.
  • the present invention is a reaction product comprising an aromatic diglycidyl ether compound (A), (meth) acrylic acid (B), and methacrylic anhydride (C) as essential reaction components (meta ) It relates to an acrylate resin.
  • the present invention further includes the following general formula (1)
  • R 1 represents a hydrogen atom or a methyl group
  • X represents the following general formulas (2-1) to (2-8)
  • each R 2 is independently a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a phenyl group, and each R 3 independently represents the number of carbon atoms.
  • Y is a hydrogen atom or a methacryloyl group.
  • (meth) acrylate resin wherein at least one of Y present in the resin is a methacryloyl group.
  • the present invention further relates to a photocurable composition containing the (meth) acrylate resin and a photopolymerization initiator.
  • the present invention further relates to a cured product of the curable composition.
  • the present invention further relates to an optical member using the curable composition.
  • cured material, moisture absorption resistance, and yellowing resistance the photocurable composition containing this, its hardened
  • FIG. 1 is a GPC chart of the (meth) acrylate resin (1) obtained in Example 1.
  • FIG. 1 is a GPC chart of the (meth) acrylate resin (1) obtained in Example 1.
  • the (meth) acrylate resin of the present invention is a reaction product containing an aromatic diglycidyl ether compound (A), (meth) acrylic acid (B), and methacrylic anhydride (C) as essential reaction components. And That is, the present invention uses a combination of (meth) acrylic acid (B) and methacrylic anhydride (C) as a (meth) acrylate agent for the aromatic diglycidyl ether compound (A). Compared to the above, it has succeeded in realizing a photocurable resin material that is excellent in heat resistance, moisture absorption resistance, and yellowing resistance in a cured product.
  • the aromatic diglycidyl ether compound (A) used in the present invention is, for example, a bisphenol type epoxy resin, a biphenyl type epoxy resin, a phenylene ether type epoxy resin, a naphthylene ether type epoxy resin, a phenol aralkyl type epoxy resin, or a naphthol aralkyl type epoxy.
  • Resin dicyclopentadiene-phenol addition reaction type epoxy resin, and the like. More specifically, the following structural formulas (3-1) to (3-8)
  • each R 2 is independently a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a phenyl group
  • each R 3 independently represents the number of carbon atoms.
  • It is any one of an alkyl group having 1 to 4, an alkoxy group having 1 to 4 carbon atoms, and a phenyl group
  • G represents a glycidyl group
  • n is an integer of 1 to 4.
  • a compound represented by any of the above may be used alone or in combination of two or more.
  • the compound represented by the structural formula (3-1) is preferable because a methacrylate resin excellent in heat resistance, moisture absorption resistance, and yellowing resistance in a cured product can be obtained.
  • the (meth) acrylic acid (B) may be either acrylic acid or methacrylic acid, or both may be used in combination.
  • methacrylic acid is preferable in that it becomes a (meth) acrylate resin excellent in heat resistance in a cured product.
  • Acrylic acid is preferable in that gas is not easily generated when the cured product is heated.
  • the reaction ratio of the aromatic diglycidyl ether compound (A), (meth) acrylic acid (B), and methacrylic anhydride (C) is an aromatic diglycidyl ether compound. It is preferable to use (meth) acrylic acid (B) and methacrylic anhydride (C) in a total amount of 0.9 to 1.1 moles per mole of epoxy group in (A).
  • the molar ratio of (meth) acrylic acid (B) to methacrylic anhydride (C) [(B) / ( C)] is preferably in the range of 1/9 to 6/4.
  • the method for producing the (meth) acrylate resin is not particularly limited.
  • the aromatic diglycidyl ether compound (A), (meth) acrylic acid (B), and methacrylic anhydride (C) are esterified.
  • examples thereof include a method of reacting in the temperature range of 100 to 150 ° C. for about 5 to 12 hours using an organic solvent as necessary in the presence of a reaction catalyst, an antioxidant and a polymerization inhibitor.
  • the (meth) acrylate resin of the present invention produced by such a method is, for example, the following general formula (1)
  • R 1 represents a hydrogen atom or a methyl group
  • X represents the following general formulas (2-1) to (2-8)
  • R 2 is independently a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a phenyl group, and R 3 is independently each having 1 carbon atom
  • Y is a hydrogen atom or a methacryloyl group.
  • at least one Y present in the resin is a methacryloyl group.
  • resin component having a molecular structure represented by the general formula (1) include compounds represented by any one of the following general formulas (1-1) to (1-3).
  • R 1 represents a hydrogen atom or a methyl group
  • X represents the following general formulas (2-1) to (2-8)
  • each R 2 is independently a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a phenyl group
  • each R 3 independently represents the number of carbon atoms.
  • It is any one of an alkyl group having 1 to 4, an alkoxy group having 1 to 4 carbon atoms, and a phenyl group, and n is an integer of 1 to 4.
  • the (meth) acryloyl group equivalent calculated from the charged amount of the raw material is in the range of 160 to 230 g / equivalent. It is preferable.
  • the photocurable composition of the present invention contains the methacrylate resin and a photopolymerization initiator.
  • photopolymerization initiator examples include diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, benzyldimethyl ketal, 1- (4-isopropylphenyl) -2-hydroxy-2 -Methylpropan-1-one, 4- (2-hydroxyethoxy) phenyl- (2-hydroxy-2-propyl) ketone, 1-hydroxycyclohexyl-phenylketone, 2-methyl-2-morpholino (4-thiomethylphenyl) ) Acetophenones such as propan-1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone; benzoins such as benzoin, benzoin methyl ether, benzoin isopropyl ether; 2, 4, 6 -Trimethylbenzoin diphenylphosphine Acylphosphine oxides such as xoxides; intramolecular bond cleavage photopolymer
  • the amount of the photopolymerization initiator added is, for example, in the range of 1 to 20 parts by mass with respect to 100 parts by mass of the photocurable composition.
  • the photocurable composition of the present invention includes other (meth) acrylate compounds other than the above-mentioned methacrylate resins, photosensitizers, curing accelerators, organic solvents, non-reactive resins, fillers, and inorganic fillers.
  • An additive component such as a dye may be included.
  • Examples of the other (meth) acrylate compounds include n-butyl (meth) acrylate, isobutyl (meth) acrylate, tert-butyl (meth) acrylate, n-pentyl (meth) acrylate, n-hexyl (meth) acrylate, n-octyl (meth) acrylate, isooctyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, glycidyl (meth) acrylate, morpholine (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) Acrylate, 4-hydroxybutyl (meth) acrylate, 2-methoxyethyl (meth) acrylate, 2-butoxyethyl (meth) acrylate, 2-ethoxyethyl (meth) acrylate, 2- (2-ethoxyeth
  • X is a hydrogen atom or a hydroxyl group
  • R 1 and R 4 are each independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms
  • R 2 is a hydrogen atom or a methyl group
  • 3 is a direct bond or a methylene group
  • m is 0 or 1.
  • two X's are each independently a hydrogen atom or a hydroxyl group
  • two R1's are each independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms
  • R2 is a hydrogen atom or a methyl group.
  • M and n are each independently 0 or 1.
  • X is independently a hydrogen atom or a hydroxyl group
  • R 1 is independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms
  • R 2 is independently a hydrogen atom or a methyl group.
  • Each R 3 is independently a direct bond or a methylene group
  • m and n are each independently 0 or 1.
  • two Xs are each independently a hydrogen atom or a hydroxyl group
  • two R1s are each independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms
  • two R2s are each independently a hydrogen atom. Or a methyl group
  • m and n are each independently 0 or 1.
  • the photocurable composition of the present invention exhibits particularly high heat resistance, moisture resistance and yellowing resistance in the cured product, it can be used in various applications such as electronic parts, molded articles, and coating applications.
  • it can be suitably used for optical member applications by taking advantage of its excellent yellowing resistance.
  • optical members include eyeglass lenses, on-chip lenses for image sensors such as CCD and CMOS, plastic lenses such as Fresnel lenses and prism lenses, optical overcoat agents, hard coat agents, antireflection films, optical fibers, and optical waveguides. , Hologram, prism lens, LED sealing material, solar cell coating material, and the like.
  • the on-chip lens and the prism lens are manufactured by, for example, a shape transfer method using a shaping die such as a mold having a lens pattern or a resin die.
  • a shaping die such as a mold having a lens pattern or a resin die.
  • a photocurable composition is applied to a shaping mold, a transparent substrate is superimposed on the surface of the composition, and an active energy ray is irradiated from the transparent substrate side to be cured.
  • the transparent substrate used here include a plastic substrate made of acrylic resin, polycarbonate resin, polyester resin, polystyrene resin, fluororesin, polyimide resin, and glass.
  • the lens sheet produced by this method can be used while being adhered to a transparent base material, or the transparent base material can be peeled off and used as a lens alone.
  • the transparent base material it is preferable to subject the surface of the transparent base material to an adhesive improvement treatment such as a primer treatment for the purpose of improving the adhesiveness between the lens and the transparent base material.
  • an adhesive improvement treatment such as a primer treatment for the purpose of improving the adhesiveness between the lens and the transparent base material.
  • the transparent substrate is peeled and used, it is preferable to treat the surface of the transparent substrate with silicone or a fluorine-based release agent so that the transparent substrate can be easily peeled off.
  • the methacrylate resin of the present invention and the other (meth) acrylate compound are used in combination, and the viscosity of the photocurable composition ( 25 ° C.) is preferably adjusted to a range of 100 mPa ⁇ s to 800 mPa ⁇ s.
  • the other (meth) acrylate compound to be used is appropriately selected depending on the desired performance. For example, it is preferable to adjust the refractive index of the cured product to be 1.5560 or more.
  • Example 1 Production of (Meth) acrylate Resin (1) A flask equipped with a thermometer, a stirrer, and a reflux condenser was charged with a bisphenol A type epoxy resin (“EPICLON 850-S” epoxy equivalent of 187 g / equivalent by DIC Corporation). ) 374 parts by weight, after adding 0.6 parts by weight of dibutylhydroxytoluene as an antioxidant and 0.2 parts by weight of methoquinone as a thermal polymerization inhibitor, 86 parts by weight of methacrylic acid, 154 parts by weight of methacrylic anhydride, triphenyl 1.8 parts by mass of phosphine was added, and an esterification reaction was carried out at 110 ° C.
  • a bisphenol A type epoxy resin (“EPICLON 850-S” epoxy equivalent of 187 g / equivalent by DIC Corporation).
  • the (meth) acryloyl group equivalent calculated from the raw material charge of the (meth) acrylate resin (1) was 205 g / equivalent.
  • the molar ratio [(B) / (C)] of methacrylic acid (B) and methacrylic anhydride (C) is 5/5.
  • the (meth) acryloyl group equivalent calculated from the raw material charge of the (meth) acrylate resin (2) was 188 g / equivalent.
  • the molar ratio [(B) / (C)] of methacrylic acid (B) to methacrylic anhydride (C) is 3/7.
  • the (meth) acryloyl group equivalent calculated from the raw material charge of the (meth) acrylate resin (3) was 176 g / equivalent.
  • the molar ratio [(B) / (C)] of methacrylic acid (B) to methacrylic anhydride (C) is 1/9.
  • the (meth) acryloyl group equivalent calculated from the raw material charge of the (meth) acrylate resin (4) was 200 g / equivalent.
  • molar ratio [(B) / (C)] of acrylic acid (B) and methacrylic anhydride (C) is 5/5.
  • the (meth) acryloyl group equivalent calculated from the raw material charge of the (meth) acrylate resin (5) was 186 g / equivalent.
  • the molar ratio [(B) / (C)] of acrylic acid (B) to methacrylic anhydride (C) is 3/7.
  • the (meth) acryloyl group equivalent calculated from the raw material charge of the (meth) acrylate resin (6) was 175 g / equivalent.
  • the molar ratio [(B) / (C)] of acrylic acid (B) to methacrylic anhydride (C) is 1/9.
  • the (meth) acryloyl group equivalent calculated from the raw material charge of the (meth) acrylate resin (1 ′) was 273 g / equivalent.
  • curable composition 1 g of photopolymerization initiator ("Irgacure 184D" manufactured by BASF) was added to 100 g of (meth) acrylate resin to prepare a curable composition.
  • photopolymerization initiator Irgacure 184D manufactured by BASF
  • the curable composition obtained above was applied on an acrylic plate so as to have a film thickness of 100 ⁇ m, and irradiated with 2000 mJ / cm 2 of ultraviolet rays with a high-pressure mercury lamp to obtain a cured product.
  • a 6 mm ⁇ 25 mm test piece was cut out from the obtained cured product, and viscoelasticity measuring device (DMA: solid viscoelasticity measuring device “RSA-G2” manufactured by Rheometric Co., Ltd.), tension method: frequency 1 Hz, heating rate 3 ° C./min. ), The temperature at which the elastic modulus change is maximum (the tan ⁇ change rate is the largest) was evaluated as the glass transition temperature.
  • Measurement of water absorption A test piece of 6 mm ⁇ 25 mm was cut out from a cured product similar to that used in the measurement of the glass transition temperature, and immersed in water at 23 ° C. for 24 hours. The weight change rate before and after immersion was evaluated as the water absorption rate.
  • the curable composition obtained above was applied on a glass plate so as to have a film thickness of 100 ⁇ m, and irradiated with 2000 mJ / cm 2 of ultraviolet rays with a high-pressure mercury lamp to obtain a laminated film.
  • the obtained laminated film was heated in an oven at 265 ° C. for 3 minutes.
  • permeability (%) of 420 nm light was measured, and it evaluated by the difference of both values.
  • the curable composition obtained in the evaluation target generated gas was applied to a thickness of 100 ⁇ m on a glass plate, a laminated film was irradiated with ultraviolet rays of 1000 mJ / cm 2 or 2000 mJ / cm 2 by a high pressure mercury lamp Obtained.
  • the obtained laminated film was heated on a hot plate at 265 ° C. for 3 minutes. At that time, whether or not gas was generated was evaluated by visual observation. No gas generation: ⁇ , gas generation and foaming: ⁇

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Epoxy Resins (AREA)

Abstract

La présente invention concerne une résine de (méth)acrylate qui peut être durcie pour former un article durci présentant d'excellentes caractéristiques de résistance à la chaleur, de résistance à l'absorption d'humidité et de résistance à la décoloration jaunâtre ; une composition photodurcissable qui contient la résine de (méth)acrylate et un produit durci de la composition photodurcissable ; et un élément optique fabriqué à l'aide de la composition photodurcissable. La résine de (méth)acrylate est caractérisée en ce qu'elle constitue un produit de réaction dont les composants de réaction essentiels sont (A) un composé d'éther diglycidylique aromatique, (B) de l'acide (méth)acrylique et (C) de l'anhydride méthacrylique ; une composition photodurcissable contenant la résine de(méth) acrylate et un produit durci de la composition photodurcissable ; et un élément optique fabriqué à l'aide de cette composition photodurcissable.
PCT/JP2016/062613 2015-05-13 2016-04-21 Résine de (méth)acrylate et élément optique Ceased WO2016181784A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP2016560023A JP6168241B2 (ja) 2015-05-13 2016-04-21 （メタ）アクリレート樹脂及び光学部材
CN201680027788.2A CN107531831A (zh) 2015-05-13 2016-04-21 (甲基)丙烯酸酯树脂及光学构件

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2015-098216 2015-05-13
JP2015098216 2015-05-13

Publications (1)

Publication Number Publication Date
WO2016181784A1 true WO2016181784A1 (fr) 2016-11-17

Family

ID=57248831

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2016/062613 Ceased WO2016181784A1 (fr) 2015-05-13 2016-04-21 Résine de (méth)acrylate et élément optique

Country Status (4)

Country Link
JP (1) JP6168241B2 (fr)
CN (1) CN107531831A (fr)
TW (1) TWI688581B (fr)
WO (1) WO2016181784A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2019112548A (ja) * 2017-12-25 2019-07-11 Dic株式会社 （メタ）アクリレート樹脂及び光学部材

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP7146409B2 (ja) * 2018-02-20 2022-10-04 ヘンケルジャパン株式会社 Ｕｖ熱硬化型接着剤組成物
WO2019198490A1 (fr) * 2018-04-10 2019-10-17 Dic株式会社 Composition de résine photosensible, objet durci, matériau isolant, matériau de résine pour réserve de soudure, et élément de soudure
KR102852357B1 (ko) * 2021-10-06 2025-08-28 삼성에스디아이 주식회사 유기발광소자 봉지용 조성물 및 이로부터 제조된 유기층을 포함하는 유기발광소자 표시장치

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5512043B2 (fr) * 1972-10-28 1980-03-29
JPH08259663A (ja) * 1995-03-24 1996-10-08 Dainippon Ink & Chem Inc 活性エネルギ−線硬化型エポキシアクリレ−ト樹脂組成物
JP2002029912A (ja) * 2000-07-05 2002-01-29 Korea Advanced Inst Of Sci Technol 歯科修復用光重合性複合レジン組成物
JP2004346315A (ja) * 2003-04-30 2004-12-09 Dainippon Ink & Chem Inc 硬化性樹脂組成物、成形材料及び燃料電池セパレーター
JP2008170767A (ja) * 2007-01-12 2008-07-24 Ricoh Co Ltd 電子写真感光体、それを用いた画像形成方法、画像形成装置及び画像形成装置用プロセスカートリッジ
JP2009069241A (ja) * 2007-09-11 2009-04-02 Ricoh Co Ltd 電子写真装置及びプロセスカートリッジ

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AT346268B (de) * 1975-02-08 1978-11-10 Werner & Pfleiderer Zum uebertragen von teigstuecken von einem ersten auf ein nachfolgendes zweites foerderband bestimmte vorrichtung
KR100995942B1 (ko) * 2003-04-30 2010-11-22 디아이씨 가부시끼가이샤 경화성 수지 조성물
US9496441B2 (en) 2011-06-01 2016-11-15 Raon Tech Co., Ltd. Solar cell module support assembly

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5512043B2 (fr) * 1972-10-28 1980-03-29
JPH08259663A (ja) * 1995-03-24 1996-10-08 Dainippon Ink & Chem Inc 活性エネルギ−線硬化型エポキシアクリレ−ト樹脂組成物
JP2002029912A (ja) * 2000-07-05 2002-01-29 Korea Advanced Inst Of Sci Technol 歯科修復用光重合性複合レジン組成物
JP2004346315A (ja) * 2003-04-30 2004-12-09 Dainippon Ink & Chem Inc 硬化性樹脂組成物、成形材料及び燃料電池セパレーター
JP2008170767A (ja) * 2007-01-12 2008-07-24 Ricoh Co Ltd 電子写真感光体、それを用いた画像形成方法、画像形成装置及び画像形成装置用プロセスカートリッジ
JP2009069241A (ja) * 2007-09-11 2009-04-02 Ricoh Co Ltd 電子写真装置及びプロセスカートリッジ

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2019112548A (ja) * 2017-12-25 2019-07-11 Dic株式会社 （メタ）アクリレート樹脂及び光学部材

Also Published As

Publication number Publication date
JP6168241B2 (ja) 2017-07-26
CN107531831A (zh) 2018-01-02
JPWO2016181784A1 (ja) 2017-05-25
TW201706319A (zh) 2017-02-16
TWI688581B (zh) 2020-03-21

Similar Documents

Publication Publication Date Title
JP6241699B2 (ja) 紫外線硬化型粘着シート、及び、粘着シート
JP5470957B2 (ja) フィルム保護層用活性エネルギー線硬化型樹脂組成物
CN105026444B (zh) 固化性组合物、透明耐热材料及其用途
TWI488910B (zh) 光硬化性樹脂組成物、使用其的光學膜的製造方法及含有其的光學膜
JP4003800B2 (ja) フィルム保護層用活性エネルギー線硬化型樹脂組成物及びそれを用いたフィルム
WO2017022770A1 (fr) Feuille adhésive autocollante, procédé de fabrication d'un stratifié comprenant une couche adhésive autocollante, stratifié comprenant une couche adhésive autocollante, dispositif d'affichage d'image, et panneau tactile
JP2014106275A (ja) ハードコートフィルム、加飾フィルム及び保護フィルム
WO2012077808A1 (fr) Feuille adhésive pour dispositif d'affichage d'image, dispositif d'affichage d'image et composition de résine adhésive
KR20140012581A (ko) 라디칼 중합성 조성물, 경화물 및 플라스틱 렌즈
KR20180018316A (ko) Uv 경화형 수지 조성물
JP6168241B2 (ja) （メタ）アクリレート樹脂及び光学部材
KR102253711B1 (ko) 점착필름 및 이를 포함하는 광학 부재
JP6630629B2 (ja) 粘着シート用硬化性組成物、及びそれを用いた粘着シート
JP4001180B2 (ja) フィルム保護層用活性エネルギー線硬化型樹脂組成物及びそれを用いたフィルム
JP5616187B2 (ja) 成形体及び成形体用樹脂組成物
KR101858328B1 (ko) 수지 적층체 및 그의 제조 방법, 및 디스플레이 전면판
WO2014028024A1 (fr) Composition adhésive à durcissement actinique et procédé de collage à l'aide de celle-ci
JP2024045606A (ja) 光学用粘着剤組成物、粘着フィルム、粘着シート、及び粘着剤層付き光学フィルム
KR102594262B1 (ko) (메타)아크릴계 수지 조성물 및 (메타)아크릴계 수지 필름
JP2024050395A (ja) 光学粘着シート
JP6454268B2 (ja) 硬化性樹脂組成物
WO2023074558A1 (fr) Feuille adhésive optique
JP2019112548A (ja) （メタ）アクリレート樹脂及び光学部材
JP7836875B2 (ja) （メタ）アクリル系樹脂フィルム、粘着シート、及び偏光フィルム
JP2012046673A (ja) 光学用接着樹脂組成物

Legal Events

Date Code Title Description
ENP Entry into the national phase

Ref document number: 2016560023

Country of ref document: JP

Kind code of ref document: A

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

Ref document number: 16792509

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 16792509

Country of ref document: EP

Kind code of ref document: A1