JP5796757B2 - 成型用光重合性樹脂組成物、及び多層成型品 - Google Patents
成型用光重合性樹脂組成物、及び多層成型品 Download PDFInfo
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- JP5796757B2 JP5796757B2 JP2014544463A JP2014544463A JP5796757B2 JP 5796757 B2 JP5796757 B2 JP 5796757B2 JP 2014544463 A JP2014544463 A JP 2014544463A JP 2014544463 A JP2014544463 A JP 2014544463A JP 5796757 B2 JP5796757 B2 JP 5796757B2
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- acrylate
- molded article
- resin
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- 239000011342 resin composition Substances 0.000 title claims description 29
- 238000000465 moulding Methods 0.000 title claims description 16
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 190
- 229920005989 resin Polymers 0.000 claims description 41
- 239000011347 resin Substances 0.000 claims description 41
- 150000001875 compounds Chemical class 0.000 claims description 40
- 239000000178 monomer Substances 0.000 claims description 38
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 37
- 239000000758 substrate Substances 0.000 claims description 27
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 26
- 229920001296 polysiloxane Polymers 0.000 claims description 23
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 22
- 239000003999 initiator Substances 0.000 claims description 22
- 239000000463 material Substances 0.000 claims description 22
- 125000003700 epoxy group Chemical group 0.000 claims description 21
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 20
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- 239000000126 substance Substances 0.000 claims description 15
- 238000002156 mixing Methods 0.000 claims description 12
- 238000006356 dehydrogenation reaction Methods 0.000 claims description 9
- 238000003776 cleavage reaction Methods 0.000 claims description 8
- 230000007017 scission Effects 0.000 claims description 8
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 claims 1
- -1 α -Glycidyl n-butyl Chemical group 0.000 description 103
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 29
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- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 15
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- 125000004386 diacrylate group Chemical group 0.000 description 10
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- 238000004519 manufacturing process Methods 0.000 description 8
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 7
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- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 5
- 239000004205 dimethyl polysiloxane Substances 0.000 description 5
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
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- 125000000217 alkyl group Chemical group 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 4
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- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 description 3
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical class OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 3
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- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 3
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- OGVXYCDTRMDYOG-UHFFFAOYSA-N dibutyl 2-methylidenebutanedioate Chemical compound CCCCOC(=O)CC(=C)C(=O)OCCCC OGVXYCDTRMDYOG-UHFFFAOYSA-N 0.000 description 1
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 1
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 1
- IEPRKVQEAMIZSS-AATRIKPKSA-N diethyl fumarate Chemical compound CCOC(=O)\C=C\C(=O)OCC IEPRKVQEAMIZSS-AATRIKPKSA-N 0.000 description 1
- ZWWQRMFIZFPUAA-UHFFFAOYSA-N dimethyl 2-methylidenebutanedioate Chemical compound COC(=O)CC(=C)C(=O)OC ZWWQRMFIZFPUAA-UHFFFAOYSA-N 0.000 description 1
- LDCRTTXIJACKKU-ONEGZZNKSA-N dimethyl fumarate Chemical compound COC(=O)\C=C\C(=O)OC LDCRTTXIJACKKU-ONEGZZNKSA-N 0.000 description 1
- 229960004419 dimethyl fumarate Drugs 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- MEGHWIAOTJPCHQ-UHFFFAOYSA-N ethenyl butanoate Chemical compound CCCC(=O)OC=C MEGHWIAOTJPCHQ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- AYLRODJJLADBOB-QMMMGPOBSA-N methyl (2s)-2,6-diisocyanatohexanoate Chemical compound COC(=O)[C@@H](N=C=O)CCCCN=C=O AYLRODJJLADBOB-QMMMGPOBSA-N 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000012778 molding material Substances 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- MNZMMCVIXORAQL-UHFFFAOYSA-N naphthalene-2,6-diol Chemical compound C1=C(O)C=CC2=CC(O)=CC=C21 MNZMMCVIXORAQL-UHFFFAOYSA-N 0.000 description 1
- DFQICHCWIIJABH-UHFFFAOYSA-N naphthalene-2,7-diol Chemical compound C1=CC(O)=CC2=CC(O)=CC=C21 DFQICHCWIIJABH-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000013307 optical fiber Substances 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- LYXOWKPVTCPORE-UHFFFAOYSA-N phenyl-(4-phenylphenyl)methanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 LYXOWKPVTCPORE-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920003216 poly(methylphenylsiloxane) Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920005650 polypropylene glycol diacrylate Polymers 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- FAIDIRVMPHBRLT-UHFFFAOYSA-N propane-1,2,3-triol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OCC(O)CO FAIDIRVMPHBRLT-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or 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 of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
- C08L33/08—Homopolymers or copolymers of acrylic acid esters
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/30—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers
- B32B27/308—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers comprising acrylic (co)polymers
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or 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 of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L35/00—Compositions of homopolymers or 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, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L35/02—Homopolymers or copolymers of esters
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
- G02B1/041—Lenses
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31507—Of polycarbonate
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31652—Of asbestos
- Y10T428/31663—As siloxane, silicone or silane
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Laminated Bodies (AREA)
- Polymerisation Methods In General (AREA)
Description
ポリオキシアルキレン構造を有するアクリレート化合物、及び、その他のモノマー型アクリロイル基含有化合物等が挙げられる。
ここで、重量平均分子量(Mw)は下記条件のゲルパーミアーションクロマトグラフィー(GPC)により測定される値である。
カラム ;東ソー株式会社製 TSK−GUARDCOLUMN SuperHZ−L+東ソー株式会社製 TSK−GEL SuperHZM−M×4
検出器 ;RI(示差屈折計)
データ処理;東ソー株式会社製 マルチステーションGPC−8020modelII
測定条件 ;カラム温度 40℃
溶媒 テトラヒドロフラン
流速 0.35ml/分
標準 ;単分散ポリスチレン
試料 ;樹脂固形分換算で0.2質量%のテトラヒドロフラン溶液をマイクロフィルターでろ過したもの(100μl)
ヒドロキノン、カテコール等の2価フェノールのジグリシジルエーテル;3,3’−ビフェニルジオール、4,4’−ビフェニルジオール等のビフェノール化合物のジグリシジルエーテル;ビスフェノールA型エポキシ樹脂、ビスフェノールB型エポキシ樹脂、ビスフェノールF型エポキシ樹脂、ビスフェノールS型エポキシ樹脂等のビスフェノール型エポキシ樹脂;1,4−ナフタレンジオール、1,5−ナフタレンジオール、1,6−ナフタレンジオール、2,6−ナフタレンジオール、2,7−ナフタレンジオール、ビナフトール、ビス(2,7−ジヒドロキシナフチル)メタン等のナフトール化合物のポリグリジシルエーテル;4,4’,4”−メチリジントリスフェノール等のトリグリシジルエーテル;フェノールノボラック型エポキシ樹脂、クレゾールノボラック樹脂等のノボラック型エポキシ樹脂
カラム ;東ソー株式会社製 TSK−GUARDCOLUMN SuperHZ−L+東ソー株式会社製 TSK−GEL SuperHZM−M×4
検出器 ;RI(示差屈折計)
データ処理;東ソー株式会社製 マルチステーションGPC−8020modelII
測定条件 ;カラム温度 40℃
溶媒 テトラヒドロフラン
流速 0.35ml/分
標準 ;単分散ポリスチレン
試料 ;樹脂固形分換算で0.2質量%のテトラヒドロフラン溶液をマイクロフィルターでろ過したもの(100μl)
ポリオール化合物(u4)とを反応させて得られるウレタン(メタ)アクリレート(U2)が挙げられる。
カラム ;東ソー株式会社製 TSK−GUARDCOLUMN SuperHZ−L
+東ソー株式会社製 TSK−GEL SuperHZM−M×4
検出器 ;RI(示差屈折計)
データ処理;東ソー株式会社製 マルチステーションGPC−8020modelII
測定条件 ;カラム温度 40℃
溶媒 テトラヒドロフラン
流速 0.35ml/分
標準 ;単分散ポリスチレン
試料 ;樹脂固形分換算で0.2質量%のテトラヒドロフラン溶液をマイクロフィルターでろ過したもの(100μl)
形状復元性の改善効果が顕著なものとなる点から、分子構造内に(メタ)アクリロイル基を有する光重合性物質(A)中、5〜30質量%の範囲であることが好ましい。
また、前記シリコーン(メタ)アクリレートは、具体的には、1分子中の側鎖、末端、あるいはその両方に、(メタ)アクリロイル基及び(メタ)アクリロイルオキシ基から選ばれる少なくとも1つの基を有するシロキサン結合を有する化合物であって、重量平均分子量(Mw)が1000〜100,000のものが好ましい。
カラム ;東ソー株式会社製 TSK−GUARDCOLUMN SuperHZ−L+東ソー株式会社製 TSK−GEL SuperHZM−M×4
検出器 ;RI(示差屈折計)
データ処理;東ソー株式会社製 マルチステーションGPC−8020modelII
測定条件 ;カラム温度 40℃
溶媒 テトラヒドロフラン
流速 0.35ml/分
標準 ;単分散ポリスチレン
試料 ;樹脂固形分換算で0.2質量%のテトラヒドロフラン溶液をマイクロフィルターでろ過したもの(100μl)
表1および表2に示す配合組成で各成分を配合することにより、成型用活性エネルギー線硬化型樹脂組成物を調製した。
得られた成型用活性エネルギー線硬化型樹脂組成物を、単位プリズム(ピッチ50μm、高さ25μm)の線状配列の凹凸形状が形成されたモールドと、表1および表2に記載された各種の透明樹脂基材との間に充填した後、超高圧水銀灯により800mJ/cm2の紫外線を透明樹脂基材側から照射して硬化させ、次いで、透明樹脂基材を活性エネルギー線硬化樹脂層と共にモールドから剥離し、必要とする形状を転写した形状付与樹脂硬化シート(L)を作製した(活性エネルギー線硬化樹脂層の厚さ20〜30μm)。
<密着性の評価>
前記形状付与樹脂硬化シート(L)を用い、JIS K−5400に準拠して下記の方法により、一次密着性および二次密着性を評価した。
一次密着:形状付与樹脂硬化シート(L)作製直後に碁盤目(100マス)剥離試験を実施し、100マス中の剥離したマスの数を評価した。
二次密着:形状付与樹脂硬化シート(L)作製後、沸騰水に10分間浸水させ、その後、上記の剥離試験を実施した結果。
本発明で屈折率は、アッべ屈折率計(アタゴ社製「NAR−3T」)を用いて測定した。温度条件は通常25℃とし、25℃で固体のものに関しては、適当な温度を設定して測定した。
(A)−1:9,9−ビス[4−(2−アクリロイルオキシエトキシ)フェニル]フルオレン
(A)−2:アクリルアクリレート[原料モノマー組成(質量%):GMA(26)/アクリル酸(14)/MMA(60)、質量平均分子量(Mw):30,000]
(A)−3:ウレタンアクリレート[原料モノマー組成(当量):TDI(2)/HEA(2)/エチレンオキサイド変性ビスフェノールA型ジオール(EO=2mol)、液屈折率:1.582]
(A)−4:ビスフェノールA型EO変性ジアクリレート(EO=4モル)
(A)−5:フェニルベンジルアクリレート
(A)−6:o−フェニルフェノキシエチルアクリレート
(A)−7:フェノキシエチルアクリレート
(B)−1:ベンゾフェノン
(B)−2:4−フェニルベンゾフェノン
(B)−3:4−ベンゾイル4’−メチルジフェニルスルフィド
(B)−4:1−[4−(4−ベンゾイルフェニルスルファニル)フェニル]−2−メチル−2−(4−メチルフェニルスルフォニル)プロパン−1−オン
(C)−1:TPO(フェニル(2,4,6−トリメチルベンゾイル)ホスフィン酸エチル)
(D)−1:シリコンポリエーテルアクリレート(エボニック社製シリコーン系添加剤「TEGORAD2200N」)
(D)−2:アクリル基含有ポリエーテル変性ジメチルシロキサン(ビックケミー・ジャパン社製シリコーン系添加剤「BYK−UV3500」)
(D)−3:ポリエーテル変性ポリジメチルシロキサン(ビックケミー・ジャパン社製シリコーン系添加剤「BYK−333」)
(D)−4:シリコーン添加剤SH−29PA(東レダウコーニング社製)
Claims (12)
- 分子構造内に(メタ)アクリロイル基を有する光重合性非シリコーン物質(A)、水素引き抜き型光重合開始剤(B)、分子内開裂型光重合開始剤(C)、およびシリコーン化合物(D)を必須成分としており、かつ、前記シリコーン化合物(D)の配合割合が、前記(A)〜(C)の合計100質量部に対して1.0〜5.0質量部となる割合であり、前記水素引き抜き型光重合開始剤(B)が1.0〜10質量部、前記分子内開裂型光重合開始剤(C)が0.5〜10質量部となる割合である成型用光硬化性樹脂組成物を、透明樹脂基材上に密着する様に成型、硬化させてなることを特徴とする多層成型品。
- 前記成型用光硬化性樹脂組成物が水素ドナーとなる化合物を含まないものである請求項1記載の多層成型品。
- 前記分子内開裂型光重合開始剤(C)が、380nm以上〜600nm以下に感光性を有する光重合性開始剤である請求項1記載の多層成型品。
- 前記シリコーン化合物(D)が、分子内に重合性不飽和二重結合を有するものである請求項1記載の多層成型品。
- 前記分子構造内に(メタ)アクリロイル基を有する光重合性物質(A)が、フルオレン骨格含有ジ(メタ)アクリレートである請求項1記載の多層成型品。
- 前記分子構造内に(メタ)アクリロイル基を有する光重合性物質(A)が、ウレタン(メタ)アクリレートである請求項1記載の多層成型品。
- 前記分子構造内に(メタ)アクリロイル基を有する光重合性物質(A)が、エポキシ基を有する(メタ)アクリル系重合体(a1)と不飽和二重結合及びカルボキシル基を有する単量体(b)とを反応させることにより得られる重合体、又は、カルボキシル基を有する(メタ)アクリル系重合体(a2)と不飽和二重結合及びエポキシ基を有する単量体(c)とを反応させることにより得られる重合体である請求項1記載の多層成型品。
- 前記分子構造内に(メタ)アクリロイル基を有する光重合性物質(A)が、(メタ)アクリル単量体である請求項1記載の多層成型品。
- 前記成型用光硬化性樹脂組成物の硬化物の屈折率が1.550以上である請求項1記載の多層成型品。
- 前記透明樹脂基材が、アクリル樹脂、ポリカーボネート樹脂、ポリエステル樹脂、ポリスチレン樹脂、フッ素樹脂、ポリイミド樹脂からなる群から選択されるものである請求項1〜9の何れか一つに記載の多層成型品。
- 前記透明樹脂基材が、ポリエステル樹脂、ポリカーボネート樹脂、アクリル樹脂、ABS樹脂、MS樹脂からなる群から選択されるものである請求項1〜9の何れか一つに記載の多層成型品。
- プラスチックレンズ、TV用導光板、光拡散シートの何れかである請求項1〜11の何れか一つに記載の多層成型品。
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EP2647673A4 (en) * | 2010-12-01 | 2016-02-10 | Nissan Chemical Ind Ltd | CURABLE COMPOSITION FOR A COATING CONTAINING A HYPER-RAMIFIED POLYMER CONTAINING FLUORINE |
CN107209284B (zh) * | 2015-02-03 | 2020-11-13 | 三井化学株式会社 | 光学材料用聚合性组合物、由该组合物得到的光学材料及塑料透镜 |
EP3279259A4 (en) * | 2015-03-30 | 2018-10-31 | Mitsubishi Gas Chemical Company, Inc. | Resin composition and molded object obtained therefrom |
JP6496820B2 (ja) | 2015-06-15 | 2019-04-10 | 三井化学株式会社 | プラスチックレンズの製造方法およびプラスチックレンズの製造装置 |
CN105504120B (zh) * | 2015-11-30 | 2018-09-21 | 东莞职业技术学院 | 一种双酚芴类丙烯酸树脂及其制备方法、量子点-彩色光敏树脂组合物及其制备方法和应用 |
EP3413102B1 (en) | 2016-02-05 | 2022-04-06 | Mitsubishi Gas Chemical Company, Inc. | Light diffusing agent, light diffusing resin composition and molded body |
TWI708803B (zh) * | 2016-03-10 | 2020-11-01 | 日商迪愛生股份有限公司 | 硬化性組成物及光學構件 |
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TWI636103B (zh) | 2018-09-21 |
US20150284556A1 (en) | 2015-10-08 |
CN104768978A (zh) | 2015-07-08 |
WO2014069332A1 (ja) | 2014-05-08 |
JPWO2014069332A1 (ja) | 2016-09-08 |
KR102043681B1 (ko) | 2019-11-12 |
KR20150081260A (ko) | 2015-07-13 |
CN104768978B (zh) | 2017-10-27 |
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