JP2014077069A - 光硬化樹脂組成物 - Google Patents
光硬化樹脂組成物 Download PDFInfo
- Publication number
- JP2014077069A JP2014077069A JP2012225697A JP2012225697A JP2014077069A JP 2014077069 A JP2014077069 A JP 2014077069A JP 2012225697 A JP2012225697 A JP 2012225697A JP 2012225697 A JP2012225697 A JP 2012225697A JP 2014077069 A JP2014077069 A JP 2014077069A
- Authority
- JP
- Japan
- Prior art keywords
- acrylate
- group
- resin composition
- monofunctional acrylate
- photocurable 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.)
- Granted
Links
- 239000011342 resin composition Substances 0.000 title claims abstract description 37
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 51
- -1 adamantanyl group Chemical group 0.000 claims abstract description 14
- 125000000524 functional group Chemical group 0.000 claims abstract description 12
- 125000003118 aryl group Chemical group 0.000 claims abstract description 11
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 claims abstract description 10
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229920000728 polyester Polymers 0.000 claims abstract description 5
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 claims abstract description 4
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims abstract description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 3
- 125000005359 phenoxyalkyl group Chemical group 0.000 claims abstract description 3
- 239000002904 solvent Substances 0.000 abstract description 15
- 230000000052 comparative effect Effects 0.000 description 13
- 229920000139 polyethylene terephthalate Polymers 0.000 description 13
- 239000005020 polyethylene terephthalate Substances 0.000 description 13
- 101000720524 Gordonia sp. (strain TY-5) Acetone monooxygenase (methyl acetate-forming) Proteins 0.000 description 10
- PSGCQDPCAWOCSH-BREBYQMCSA-N [(1r,3r,4r)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] prop-2-enoate Chemical compound C1C[C@@]2(C)[C@H](OC(=O)C=C)C[C@@H]1C2(C)C PSGCQDPCAWOCSH-BREBYQMCSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 7
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 6
- 150000002148 esters Chemical group 0.000 description 6
- 238000002156 mixing Methods 0.000 description 5
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 4
- XLPJNCYCZORXHG-UHFFFAOYSA-N 1-morpholin-4-ylprop-2-en-1-one Chemical compound C=CC(=O)N1CCOCC1 XLPJNCYCZORXHG-UHFFFAOYSA-N 0.000 description 4
- RZVINYQDSSQUKO-UHFFFAOYSA-N 2-phenoxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC1=CC=CC=C1 RZVINYQDSSQUKO-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000000853 adhesive Substances 0.000 description 4
- 230000001070 adhesive effect Effects 0.000 description 4
- GCTPMLUUWLLESL-UHFFFAOYSA-N benzyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=CC=C1 GCTPMLUUWLLESL-UHFFFAOYSA-N 0.000 description 4
- 238000001723 curing Methods 0.000 description 4
- 150000002009 diols Chemical class 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 150000003077 polyols Chemical class 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- GNWBLLYJQXKPIP-ZOGIJGBBSA-N (1s,3as,3bs,5ar,9ar,9bs,11as)-n,n-diethyl-6,9a,11a-trimethyl-7-oxo-2,3,3a,3b,4,5,5a,8,9,9b,10,11-dodecahydro-1h-indeno[5,4-f]quinoline-1-carboxamide Chemical compound CN([C@@H]1CC2)C(=O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](C(=O)N(CC)CC)[C@@]2(C)CC1 GNWBLLYJQXKPIP-ZOGIJGBBSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- WHNPOQXWAMXPTA-UHFFFAOYSA-N 3-methylbut-2-enamide Chemical compound CC(C)=CC(N)=O WHNPOQXWAMXPTA-UHFFFAOYSA-N 0.000 description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
- 150000003926 acrylamides Chemical class 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 238000000016 photochemical curing Methods 0.000 description 3
- 229920005668 polycarbonate resin Polymers 0.000 description 3
- 239000004431 polycarbonate resin Substances 0.000 description 3
- 229920001228 polyisocyanate Polymers 0.000 description 3
- 239000005056 polyisocyanate Substances 0.000 description 3
- 239000003505 polymerization initiator Substances 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 238000005452 bending Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229920002379 silicone rubber Polymers 0.000 description 2
- 239000004945 silicone rubber Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- HHQAGBQXOWLTLL-UHFFFAOYSA-N (2-hydroxy-3-phenoxypropyl) prop-2-enoate Chemical compound C=CC(=O)OCC(O)COC1=CC=CC=C1 HHQAGBQXOWLTLL-UHFFFAOYSA-N 0.000 description 1
- ZMZHRHTZJDBLEX-UHFFFAOYSA-N (2-phenylphenyl) prop-2-enoate Chemical class C=CC(=O)OC1=CC=CC=C1C1=CC=CC=C1 ZMZHRHTZJDBLEX-UHFFFAOYSA-N 0.000 description 1
- PHPRWKJDGHSJMI-UHFFFAOYSA-N 1-adamantyl prop-2-enoate Chemical compound C1C(C2)CC3CC2CC1(OC(=O)C=C)C3 PHPRWKJDGHSJMI-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- TUAJZTAVXLCEGA-UHFFFAOYSA-N 1-hydroxyethyl prop-2-enoate Chemical compound CC(O)OC(=O)C=C TUAJZTAVXLCEGA-UHFFFAOYSA-N 0.000 description 1
- ZMIRFCWMDNOYEN-UHFFFAOYSA-N 1-phosphorosooxyethane Chemical compound CCOP=O ZMIRFCWMDNOYEN-UHFFFAOYSA-N 0.000 description 1
- IAMASUILMZETHW-UHFFFAOYSA-N 2-(2-hydroxyethoxy)-1-phenoxyethanol;prop-2-enoic acid Chemical compound OC(=O)C=C.OCCOCC(O)OC1=CC=CC=C1 IAMASUILMZETHW-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- GJKGAPPUXSSCFI-UHFFFAOYSA-N 2-Hydroxy-4'-(2-hydroxyethoxy)-2-methylpropiophenone Chemical compound CC(C)(O)C(=O)C1=CC=C(OCCO)C=C1 GJKGAPPUXSSCFI-UHFFFAOYSA-N 0.000 description 1
- PCKZAVNWRLEHIP-UHFFFAOYSA-N 2-hydroxy-1-[4-[[4-(2-hydroxy-2-methylpropanoyl)phenyl]methyl]phenyl]-2-methylpropan-1-one Chemical compound C1=CC(C(=O)C(C)(O)C)=CC=C1CC1=CC=C(C(=O)C(C)(C)O)C=C1 PCKZAVNWRLEHIP-UHFFFAOYSA-N 0.000 description 1
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 1
- QISZCVLALJOROC-UHFFFAOYSA-N 3-(2-hydroxyethyl)-4-(2-prop-2-enoyloxyethyl)phthalic acid Chemical compound OCCC1=C(CCOC(=O)C=C)C=CC(C(O)=O)=C1C(O)=O QISZCVLALJOROC-UHFFFAOYSA-N 0.000 description 1
- UXTGJIIBLZIQPK-UHFFFAOYSA-N 3-(2-prop-2-enoyloxyethyl)phthalic acid Chemical compound OC(=O)C1=CC=CC(CCOC(=O)C=C)=C1C(O)=O UXTGJIIBLZIQPK-UHFFFAOYSA-N 0.000 description 1
- UVRCNEIYXSRHNT-UHFFFAOYSA-N 3-ethylpent-2-enamide Chemical compound CCC(CC)=CC(N)=O UVRCNEIYXSRHNT-UHFFFAOYSA-N 0.000 description 1
- SBVKVAIECGDBTC-UHFFFAOYSA-N 4-hydroxy-2-methylidenebutanamide Chemical compound NC(=O)C(=C)CCO SBVKVAIECGDBTC-UHFFFAOYSA-N 0.000 description 1
- 229920001634 Copolyester Polymers 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- KBLWLMPSVYBVDK-UHFFFAOYSA-N cyclohexyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCCC1 KBLWLMPSVYBVDK-UHFFFAOYSA-N 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 230000006355 external stress Effects 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- LUCXVPAZUDVVBT-UHFFFAOYSA-N methyl-[3-(2-methylphenoxy)-3-phenylpropyl]azanium;chloride Chemical compound Cl.C=1C=CC=CC=1C(CCNC)OC1=CC=CC=C1C LUCXVPAZUDVVBT-UHFFFAOYSA-N 0.000 description 1
- QNILTEGFHQSKFF-UHFFFAOYSA-N n-propan-2-ylprop-2-enamide Chemical compound CC(C)NC(=O)C=C QNILTEGFHQSKFF-UHFFFAOYSA-N 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 238000004080 punching Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- MUTNCGKQJGXKEM-UHFFFAOYSA-N tamibarotene Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1NC(=O)C1=CC=C(C(O)=O)C=C1 MUTNCGKQJGXKEM-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Abstract
【解決手段】ポリエステル主鎖のウレタンアクリレートと芳香環を有する単官能アクリレートが含まれ、嵩高官能基を有する単官能アクリレート或いは単官能アクリルアミドのいずれかが含まれ、また、芳香環を有する単官能アクリレートと嵩高官能基を有する単官能アクリレートと単官能アクリルアミドが含まれる光硬化樹脂組成物であり、前記芳香環を有する単官能アクリレート単官能アクリレートがベンジル基、フェノキシアルキル基を有する単官能アクリレートであり、前記嵩高官能基を有する単官能アクリレートがジシクロペンタニル基、イソボルニル基、アダマンタニル基、テトラヒドロフラニル基、シクロヘキサニル基を有する単官能アクリレートであることが好ましい。
【選択図】なし
Description
性および曲げ加工性に優れたポリカーボネート樹脂積層体となることを開示さしている。
)に、ライトアクリレートPO−AをV#160に変えた以外、実施例7と同じく行い実施例8の光硬化樹脂組成物とした。
実施例11の ライトアクリレートIB−XAを30重量部に、ACMOおよびライトアクリレートPO−Aを無配合に変えた以外、実施例11と同じく行い比較例1の光硬化樹脂組成物とした。
実施例11の ACMOを30重量部に、ライトアクリレートIB−XAおよびライトアクリレートPO−Aを無配合に変えた以外、実施例11と同じく行い比較例2の光硬化樹脂組成物とした。
実施例11の ライトアクリレートPO−Aを30重量部に、ライトアクリレートIB−XAを無配合に変えた以外、実施例11と同じく行い比較例3の光硬化樹脂組成物とした。
実施例11の ライトアクリレートIB−XAを15重量部、ACMOを15重量部に、ライトアクリレートPO−Aを無配合に変えた以外、実施例11と同じく行い比較例4の光硬化樹脂組成物とした。
実施例1の RX43−21をSUA−008(亜細亜工業(株)、商品名、ウレタンアクリレートオリゴマー、主鎖 エーテル系、1分子当たりのアクリロイル基2、数平均分子量16300)に変えた以外、実施例1と同じく行い比較例5の光硬化樹脂組成物とした。
変化率=浸漬後数値÷常態数値×100
Claims (4)
- ポリエステル主鎖のウレタンアクリレートと芳香環を有する単官能アクリレートが含まれ、嵩高官能基を有する単官能アクリレート或いは単官能アクリルアミドのいずれかが含まれることを特徴とする光硬化樹脂組成物。
- 嵩高官能基を有する単官能アクリレートおよび単官能アクリルアミドが含まれることを特徴とする請求項1に記載の光硬化樹脂組成物。
- 芳香環を有する単官能アクリレートがベンジル基、フェノキシアルキル基を有する単官能アクリレートである請求項1乃至2いずれかに記載の光硬化樹脂組成物。
- 嵩高官能基を有する単官能アクリレートがジシクロペンタニル基、イソボルニル基、アダマンタニル基、テトラヒドロフラニル基、シクロヘキサニル基を有する単官能アクリレートである請求項1乃至3いずれかに記載の光硬化樹脂組成物。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2012225697A JP6144893B2 (ja) | 2012-10-11 | 2012-10-11 | 光硬化性樹脂組成物 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2012225697A JP6144893B2 (ja) | 2012-10-11 | 2012-10-11 | 光硬化性樹脂組成物 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2014077069A true JP2014077069A (ja) | 2014-05-01 |
JP6144893B2 JP6144893B2 (ja) | 2017-06-07 |
Family
ID=50782654
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2012225697A Expired - Fee Related JP6144893B2 (ja) | 2012-10-11 | 2012-10-11 | 光硬化性樹脂組成物 |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP6144893B2 (ja) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2016089156A (ja) * | 2014-10-31 | 2016-05-23 | 三洋化成工業株式会社 | 活性エネルギー線硬化性樹脂組成物 |
US10975191B2 (en) | 2016-06-01 | 2021-04-13 | Mitsubishi Gas Chemical Company, Inc. | Urethane (meth)acrylate, method for manufacturing urethane (meth)acrylate, curable composition, cured article, and method for manufacturing cured article |
EP3864058A4 (en) * | 2018-10-08 | 2022-07-20 | Henkel AG & Co. KGaA | PHOTOCURABLE COMPOSITION |
WO2024024713A1 (ja) * | 2022-07-28 | 2024-02-01 | 株式会社レゾナック・パッケージング | 電池用包装材 |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0748422A (ja) * | 1993-08-06 | 1995-02-21 | Denki Kagaku Kogyo Kk | 活性エネルギー線硬化性樹脂組成物 |
JPH1060065A (ja) * | 1996-08-20 | 1998-03-03 | Nippon Kayaku Co Ltd | 樹脂組成物、封止用樹脂組成物及びその硬化物 |
JP2002503282A (ja) * | 1997-06-09 | 2002-01-29 | デー エス エム エヌ.ヴェー. | ポリエステル主鎖を有するウレタンオリゴマーからなる輻射線硬化性組成物 |
JP2004359722A (ja) * | 2003-06-02 | 2004-12-24 | Toyobo Co Ltd | 活性光線硬化型樹脂組成物、インキ、およびこれを塗布した積層物 |
JP2006273895A (ja) * | 2005-03-28 | 2006-10-12 | Kyoeisha Chem Co Ltd | 不飽和基含有ウレタンオリゴマーおよびそれが重合した硬化物 |
JP2008031189A (ja) * | 2005-07-22 | 2008-02-14 | Bridgestone Corp | シール用材料及びガスケット |
JP2008031246A (ja) * | 2006-07-27 | 2008-02-14 | Dainippon Ink & Chem Inc | 接着剤用硬化型樹脂組成物 |
JP2010225322A (ja) * | 2009-03-19 | 2010-10-07 | Toagosei Co Ltd | 電極被覆用光硬化型組成物 |
-
2012
- 2012-10-11 JP JP2012225697A patent/JP6144893B2/ja not_active Expired - Fee Related
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0748422A (ja) * | 1993-08-06 | 1995-02-21 | Denki Kagaku Kogyo Kk | 活性エネルギー線硬化性樹脂組成物 |
JPH1060065A (ja) * | 1996-08-20 | 1998-03-03 | Nippon Kayaku Co Ltd | 樹脂組成物、封止用樹脂組成物及びその硬化物 |
JP2002503282A (ja) * | 1997-06-09 | 2002-01-29 | デー エス エム エヌ.ヴェー. | ポリエステル主鎖を有するウレタンオリゴマーからなる輻射線硬化性組成物 |
JP2004359722A (ja) * | 2003-06-02 | 2004-12-24 | Toyobo Co Ltd | 活性光線硬化型樹脂組成物、インキ、およびこれを塗布した積層物 |
JP2006273895A (ja) * | 2005-03-28 | 2006-10-12 | Kyoeisha Chem Co Ltd | 不飽和基含有ウレタンオリゴマーおよびそれが重合した硬化物 |
JP2008031189A (ja) * | 2005-07-22 | 2008-02-14 | Bridgestone Corp | シール用材料及びガスケット |
JP2008031246A (ja) * | 2006-07-27 | 2008-02-14 | Dainippon Ink & Chem Inc | 接着剤用硬化型樹脂組成物 |
JP2010225322A (ja) * | 2009-03-19 | 2010-10-07 | Toagosei Co Ltd | 電極被覆用光硬化型組成物 |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2016089156A (ja) * | 2014-10-31 | 2016-05-23 | 三洋化成工業株式会社 | 活性エネルギー線硬化性樹脂組成物 |
US10975191B2 (en) | 2016-06-01 | 2021-04-13 | Mitsubishi Gas Chemical Company, Inc. | Urethane (meth)acrylate, method for manufacturing urethane (meth)acrylate, curable composition, cured article, and method for manufacturing cured article |
EP3864058A4 (en) * | 2018-10-08 | 2022-07-20 | Henkel AG & Co. KGaA | PHOTOCURABLE COMPOSITION |
US11597788B2 (en) | 2018-10-08 | 2023-03-07 | Henkel Ag & Co. Kgaa | Light curable composition |
WO2024024713A1 (ja) * | 2022-07-28 | 2024-02-01 | 株式会社レゾナック・パッケージング | 電池用包装材 |
Also Published As
Publication number | Publication date |
---|---|
JP6144893B2 (ja) | 2017-06-07 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP6277383B2 (ja) | (メタ)アクリルアミド系ウレタンオリゴマー及びそれを含有する活性エネルギー線硬化性樹脂組成物 | |
JP5764040B2 (ja) | 光学用紫外線硬化型樹脂組成物、硬化物及び表示装置 | |
JP6443991B2 (ja) | エンチオール系硬化性組成物およびその硬化物 | |
JP5886090B2 (ja) | 活性エネルギー線硬化性樹脂組成物及びコーティング剤 | |
JP2007030479A (ja) | 活性エネルギー線硬化樹脂積層体およびその製造方法 | |
KR20130140537A (ko) | 라디칼 경화성 핫 멜트 우레탄 수지 조성물, 및 광학용 성형체 | |
JP5566216B2 (ja) | 活性エネルギー線硬化型樹脂組成物、及びそれを用いてなるコーティング剤組成物、並びに硬化塗膜 | |
TWI458630B (zh) | Laminated body and its use | |
JPWO2010079584A1 (ja) | 粘着剤及び粘着フィルム | |
JP6144893B2 (ja) | 光硬化性樹脂組成物 | |
JP2012126839A (ja) | 光学用紫外線硬化型樹脂組成物、硬化物及び表示装置 | |
JP6358789B2 (ja) | 活性エネルギー線硬化性樹脂組成物及びコーティング剤 | |
JP6075443B2 (ja) | 活性エネルギー線硬化型塗料組成物 | |
JP6917132B2 (ja) | 光硬化性樹脂組成物 | |
JP2016179966A (ja) | 爪化粧用光硬化性組成物および爪化粧料 | |
JP2014065902A (ja) | 活性エネルギー線硬化性樹脂組成物及びコーティング剤 | |
JP2016199663A (ja) | 紫外線硬化型粘着剤組成物および粘着シート | |
JP7054753B1 (ja) | ハードコート樹脂組成物 | |
JP2014162853A (ja) | 活性エネルギー線硬化型接着剤組成物及びそれを用いた接着方法 | |
JP6335853B2 (ja) | 手芸用紫外線硬化樹脂組成物 | |
JP2009091586A (ja) | 活性エネルギー線硬化樹脂シート | |
JP2018002765A (ja) | 注形用紫外線硬化樹脂組成物 | |
JP6331115B2 (ja) | 環状オレフィン樹脂フィルム | |
JP7376849B2 (ja) | 活性エネルギー線硬化型コーティング剤組成物、硬化物、積層体 | |
JP2014052538A (ja) | 液晶パネル用光硬化型樹脂組成物、並びにその硬化方法、硬化物 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20150903 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20160715 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20160728 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20160920 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20170216 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20170331 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20170420 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20170512 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 6144893 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R157 | Certificate of patent or utility model (correction) |
Free format text: JAPANESE INTERMEDIATE CODE: R157 |
|
LAPS | Cancellation because of no payment of annual fees |