JP2006008819A - Photocurable composition - Google Patents
Photocurable composition Download PDFInfo
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- JP2006008819A JP2006008819A JP2004187360A JP2004187360A JP2006008819A JP 2006008819 A JP2006008819 A JP 2006008819A JP 2004187360 A JP2004187360 A JP 2004187360A JP 2004187360 A JP2004187360 A JP 2004187360A JP 2006008819 A JP2006008819 A JP 2006008819A
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- 239000000203 mixture Substances 0.000 title claims abstract description 32
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 23
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 18
- 229920000642 polymer Polymers 0.000 claims abstract description 17
- 229920001971 elastomer Polymers 0.000 claims abstract description 16
- 239000000806 elastomer Substances 0.000 claims abstract description 14
- 239000005062 Polybutadiene Substances 0.000 claims abstract description 13
- 229920002857 polybutadiene Polymers 0.000 claims abstract description 13
- 239000003999 initiator Substances 0.000 claims abstract description 10
- 125000002723 alicyclic group Chemical group 0.000 claims abstract description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 5
- -1 acryl group Chemical group 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 229920002367 Polyisobutene Polymers 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000005647 linker group Chemical group 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000000962 organic group Chemical group 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 238000000016 photochemical curing Methods 0.000 claims 1
- 239000002904 solvent Substances 0.000 abstract description 15
- 230000004888 barrier function Effects 0.000 abstract description 8
- 239000003566 sealing material Substances 0.000 abstract description 4
- 230000035699 permeability Effects 0.000 description 14
- 239000011347 resin Substances 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 238000001723 curing Methods 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 239000000565 sealant Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 230000001678 irradiating effect Effects 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- FGTYTUFKXYPTML-UHFFFAOYSA-N 2-benzoylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 FGTYTUFKXYPTML-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- 244000028419 Styrax benzoin Species 0.000 description 2
- 235000000126 Styrax benzoin Nutrition 0.000 description 2
- 235000008411 Sumatra benzointree Nutrition 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000008602 contraction Effects 0.000 description 2
- 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 2
- 239000003822 epoxy resin Substances 0.000 description 2
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 2
- 239000010419 fine particle Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 235000019382 gum benzoic Nutrition 0.000 description 2
- 239000011256 inorganic filler Substances 0.000 description 2
- 229910003475 inorganic filler Inorganic materials 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 229920001195 polyisoprene Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- 238000013519 translation Methods 0.000 description 2
- 230000014616 translation Effects 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 1
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 1
- 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 1
- SWFHGTMLYIBPPA-UHFFFAOYSA-N (4-methoxyphenyl)-phenylmethanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 SWFHGTMLYIBPPA-UHFFFAOYSA-N 0.000 description 1
- MLKIVXXYTZKNMI-UHFFFAOYSA-N 1-(4-dodecylphenyl)-2-hydroxy-2-methylpropan-1-one Chemical compound CCCCCCCCCCCCC1=CC=C(C(=O)C(C)(C)O)C=C1 MLKIVXXYTZKNMI-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- YIKSHDNOAYSSPX-UHFFFAOYSA-N 1-propan-2-ylthioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(C)C YIKSHDNOAYSSPX-UHFFFAOYSA-N 0.000 description 1
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 description 1
- LCHAFMWSFCONOO-UHFFFAOYSA-N 2,4-dimethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC(C)=C3SC2=C1 LCHAFMWSFCONOO-UHFFFAOYSA-N 0.000 description 1
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 1
- ZCDADJXRUCOCJE-UHFFFAOYSA-N 2-chlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3SC2=C1 ZCDADJXRUCOCJE-UHFFFAOYSA-N 0.000 description 1
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 1
- QPXVRLXJHPTCPW-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-(4-propan-2-ylphenyl)propan-1-one Chemical compound CC(C)C1=CC=C(C(=O)C(C)(C)O)C=C1 QPXVRLXJHPTCPW-UHFFFAOYSA-N 0.000 description 1
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 1
- MYISVPVWAQRUTL-UHFFFAOYSA-N 2-methylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC=C3SC2=C1 MYISVPVWAQRUTL-UHFFFAOYSA-N 0.000 description 1
- SKKHNUKNMQLBTJ-UHFFFAOYSA-N 3-bicyclo[2.2.1]heptanyl 2-methylprop-2-enoate Chemical compound C1CC2C(OC(=O)C(=C)C)CC1C2 SKKHNUKNMQLBTJ-UHFFFAOYSA-N 0.000 description 1
- CUXGDKOCSSIRKK-UHFFFAOYSA-N 7-methyloctyl prop-2-enoate Chemical compound CC(C)CCCCCCOC(=O)C=C CUXGDKOCSSIRKK-UHFFFAOYSA-N 0.000 description 1
- 229920003026 Acene Polymers 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 102100026735 Coagulation factor VIII Human genes 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 101000911390 Homo sapiens Coagulation factor VIII Proteins 0.000 description 1
- 239000004831 Hot glue Substances 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- DBHQYYNDKZDVTN-UHFFFAOYSA-N [4-(4-methylphenyl)sulfanylphenyl]-phenylmethanone Chemical compound C1=CC(C)=CC=C1SC1=CC=C(C(=O)C=2C=CC=CC=2)C=C1 DBHQYYNDKZDVTN-UHFFFAOYSA-N 0.000 description 1
- 150000008062 acetophenones Chemical class 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 229960002130 benzoin Drugs 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
- 150000008366 benzophenones Chemical class 0.000 description 1
- 230000001588 bifunctional effect Effects 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
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000002704 decyl 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])* 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 230000001815 facial effect Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 229910001416 lithium ion Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000013008 moisture curing Methods 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
- 239000012766 organic filler 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
- 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
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 125000004079 stearyl 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])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000010998 test method Methods 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
- 230000007704 transition Effects 0.000 description 1
Abstract
Description
本発明は紫外線や可視光等の活性エネルギー線の照射により速やかに重合し、その硬化物が柔軟でありながら耐溶剤性、透湿バリア性に優れる光硬化性組成物に関する。 The present invention relates to a photocurable composition that is rapidly polymerized by irradiation with active energy rays such as ultraviolet rays and visible light, and is excellent in solvent resistance and moisture permeability barrier properties while being cured.
耐溶剤性および／または透湿バリア性に優れた技術として、多官能（メタ）アクリル酸エステル、橋かけ環構造を有する２官能（メタ）アクリル酸エステルおよび光重合開始剤からなる光硬化性組成物（特許第２９５３５９８号公報）、分子中に（メタ）アクリル基と加水分解性基を有するポリイソブチレン、光重合開始剤および湿気硬化触媒からなる光および湿気硬化性組成物（特開２０００−１７８５３５号公報）、エポキシ樹脂、ゴム状ポリマー微粒子、無機充填剤、熱潜在性エポキシ硬化剤および高軟化点ポリマー微粒子からなる熱硬化性組成物（特開２０００−３４７２０３号公報）、特定の化学構造を有するエポキシ化合物を含有するカチオン重合性化合物、ラジカル重合性化合物、光カチオン重合開始剤および光ラジカル重合開始剤からなる光硬化性組成物（特開２００２−２５６０６２号公報）、ポリオレフィンとポリビニルアルコール、相溶化剤、可塑剤、加工助剤および酸化防止剤からなるフィルム、シート、成形体加工用組成物（特表２００２−５３７４０８号公報）等が開示されている。 As a technology excellent in solvent resistance and / or moisture permeability barrier properties, a photocurable composition comprising a polyfunctional (meth) acrylate ester, a bifunctional (meth) acrylate ester having a bridged ring structure, and a photopolymerization initiator (Patent No. 2953598), a light and moisture curable composition comprising a polyisobutylene having a (meth) acrylic group and a hydrolyzable group in the molecule, a photopolymerization initiator and a moisture curing catalyst (JP 2000-178535 A). No.), epoxy resin, rubber-like polymer fine particles, inorganic filler, thermolatent epoxy curing agent and high softening point polymer fine particles (Japanese Patent Laid-Open No. 2000-347203), a specific chemical structure Cationic polymerizable compound, radical polymerizable compound, photocationic polymerization initiator and photoradical polymerization containing epoxy compound having Photocurable composition comprising an initiator (Japanese Patent Laid-Open No. 2002-256062), film, sheet and molded article composition comprising polyolefin and polyvinyl alcohol, compatibilizer, plasticizer, processing aid and antioxidant (Japanese translations of PCT publication No. 2002-537408 gazette) etc. are disclosed.
一方、反応性樹脂中にエラストマーを分散させる技術や反応性樹脂骨格中にエラストマー成分を導入する技術に関しても報告例があり、エポキシ樹脂由来の化学構造とポリシロキサン構造を有し、かつ官能基としてエポキシ基を有する共重合体（特公昭６１−４８５４４号公報、特開昭６３−３０１２２０号公報、特開平２−２０８３１４号公報、特開平６−１６７７３号公報、特許第２７０３０４５号公報、特許第３１７８０６６号公報および特開２００２−２４９５８４号公報）、分子中にポリブタジエン骨格を有する（メタ）アクリレート系樹脂を用いた低透湿度ホットメルト接着剤（特開平３−２７８３３３号公報、特開平４−２５８８２５号公報、特開平５−０１２７１４号公報）、５℃以下のガラス店転移点を有するポリマーとエチレン系不飽和化合物がマトリックス相をなす感光性樹脂（特開平１０−７８６５７号公報、特開平１０−１２３７１０号公報）、アクリル酸エステルモノマーと２０℃以下のガラス転移点を有するゴム弾性体から成る樹脂充填材（特開平１０−３１６８２６号公報）等に開示されている。
一般に耐溶剤性や透湿バリア性を高めるためには硬化物の架橋密度を高くする必要があり、その結果として硬化物が硬くなる傾向にある。このような材料をシール材として用いた場合、ヒートサイクルによる被着材の膨張、収縮に追従できず、シール材が破損して内部流体の漏れの原因となる。本発明は上記の問題を解決することを目的とする。 In general, in order to improve the solvent resistance and moisture permeability barrier property, it is necessary to increase the crosslinking density of the cured product, and as a result, the cured product tends to be hard. When such a material is used as the sealing material, it cannot follow the expansion and contraction of the adherend due to the heat cycle, and the sealing material is damaged, causing internal fluid to leak. The present invention aims to solve the above problems.
前記課題を目的を達成するため鋭意研究した結果、（Ａ）末端に（メタ）アクリル基を有し主骨格を水添されたポリブタジエンである重合体と、（Ｂ）飽和脂肪族エラストマーと、（Ｃ）光重合開始剤の（Ａ）〜（Ｃ）を主成分とする光硬化性組成物により、あるいは、前記（Ａ）〜（Ｃ）の組成物に、（Ｄ）炭素数５以上の鎖状脂肪族または脂環式単官能（メタ）アクリレートをさらに添加した（Ａ）〜（Ｄ）を主成分とする光硬化性組成物により課題を解決した。 As a result of earnest research to achieve the above object, (A) a polymer which is a polybutadiene having a (meth) acrylic group at the terminal and hydrogenated main skeleton, (B) a saturated aliphatic elastomer, C) The photopolymerization initiator (A) to (C) as a main component, or the composition (A) to (C) described above, (D) a chain having 5 or more carbon atoms. The problems were solved by a photocurable composition comprising (A) to (D) as main components, to which a further aliphatic or alicyclic monofunctional (meth) acrylate was further added.
本発明における末端に（メタ）アクリル基を有し主骨格を水添（水素化）されたポリブタジエン骨格を持つ重合体（Ａ）は下記式で表される。
（式中、Ｒ１およびＲ２はそれぞれ独立して水素原子またはメチル基を、Ｒ３およびＲ４はそれぞれ独立して単なる連結基、酸素原子または炭素数１〜１６の置換、非置換の二価の有機基を表す。ｘ：ｙ＝０〜１００：１００〜０、ｎは１５〜１５０である。）
The polymer (A) having a polybutadiene skeleton having a (meth) acrylic group at the terminal and hydrogenating (hydrogenating) the main skeleton is represented by the following formula.
(Wherein R 1 and R 2 are each independently a hydrogen atom or a methyl group, and R 3 and R 4 are each independently a simple linking group, an oxygen atom, or a substituted or unsubstituted group having 1 to 16 carbon atoms. Represents an organic group having a valence of x: y = 0 to 100: 100 to 0, and n is 15 to 150.)
本発明における飽和脂肪族エラストマー（Ｂ）は、本発明組成物の柔軟性・透湿度性・耐溶剤性の向上を目的として用いられるものである。この成分（Ｂ）としては、成分（Ａ）に相溶し、組成物の硬化性、硬化物の物性等に問題を生じないもので、常温にてゴム弾性を示すものが好ましく、ポリブタジエンやポリイソブチレン等が挙げられる。また添加量は成分（Ａ）に対して２０〜８０重量部の割合で添加することが好ましい。２０重量部未満では十分な耐溶剤性を得ることが困難であり、また８０重量部を超えると硬化後に成分（Ａ）と成分（Ｂ）が分離や、著しい透湿性の低下となる。 The saturated aliphatic elastomer (B) in the present invention is used for the purpose of improving the flexibility, moisture permeability and solvent resistance of the composition of the present invention. As this component (B), those which are compatible with the component (A) and do not cause a problem in the curability of the composition, the physical properties of the cured product, etc., and exhibit rubber elasticity at room temperature are preferred. And isobutylene. The addition amount is preferably 20 to 80 parts by weight based on the component (A). When the amount is less than 20 parts by weight, it is difficult to obtain sufficient solvent resistance. When the amount exceeds 80 parts by weight, the component (A) and the component (B) are separated after curing and the moisture permeability is remarkably lowered.
本発明で用いられる光重合開始剤（Ｃ）は、化学構造（分子結合エネルギー）の差により、分子内開裂型（Ｐ１型）と水素引き抜き型（Ｐ２型）に分類される。Ｐ１型の具体例としては、４−フェノキシジクロロアセトフェノン、４−ｔ−ブチル−ジクロロアセトフェノン、４−ｔ−ブチル−トリクロロアセトフェノン、ジエトキシアセトフェノン、２−ヒドロキシ−２−メチル−１−フェニルプロパン−１−オン、１−（４−イソプロピルフェニル）−２−ヒドロキシ−２−メチルプロパン−１−オン、１−（４−ドデシルフェニル）−２−ヒドロキシ−２−メチルプロパン−１−オン、４−（２−ヒドロキシエトキシ）−フェニル（２−ヒドロキシ−２−プロピル）ケトン、１−ヒドロキシシクロヘキシルフェニルケトン等のアセトフェノン類、ベンゾイン、ベンゾインメチルーテル、ベンゾインエチルエーテル、ベンジルジメチルケタール等のベンゾイン類、アシルフォシフィンオキサイド類、チタノセン化合物等が挙げられる。また、Ｐ２型の具体例としては、ベンゾフェノン、ベンゾイルベンゾイックアシッド、ベンゾイルベンゾイックアシッドメチルエーテル、４−フェニルベンゾフェノン、ヒドロキシベンゾフェノン、４−ベンゾイル−４’−メチルジフェニルサルファイド、３，３’−メチル−４−メトキシベンゾフェノン等のベンゾフェノン類、チオキサントン、２−クロロチオキサントン、２−メチルチオキサントン、２，４−ジメチルチオキサントン、イソプロピルチオキサントン等のチオキサントン類が挙げられる。光ラジカル重合開始剤は１種または２種以上を用いることができ、Ｐ１型同士、Ｐ２型同士あるいはＰ１型とＰ２型を併用しても良い。また、本発明の光硬化性組成物は、０．５〜５重量％の割合で含有していることが好ましい。 The photopolymerization initiator (C) used in the present invention is classified into an intramolecular cleavage type (P1 type) and a hydrogen abstraction type (P2 type) depending on the difference in chemical structure (molecular bond energy). Specific examples of the P1 type include 4-phenoxydichloroacetophenone, 4-t-butyl-dichloroacetophenone, 4-t-butyl-trichloroacetophenone, diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropane-1 -One, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one, 1- (4-dodecylphenyl) -2-hydroxy-2-methylpropan-1-one, 4- ( Acetophenones such as 2-hydroxyethoxy) -phenyl (2-hydroxy-2-propyl) ketone and 1-hydroxycyclohexyl phenylketone, benzoins such as benzoin, benzoin methyl ether, benzoin ethyl ether and benzyldimethyl ketal, acylphosphines Fin oxides, Tanosen compounds. Specific examples of the P2 type include benzophenone, benzoyl benzoic acid, benzoyl benzoic acid methyl ether, 4-phenylbenzophenone, hydroxybenzophenone, 4-benzoyl-4′-methyldiphenyl sulfide, 3,3′-methyl- Examples include benzophenones such as 4-methoxybenzophenone, and thioxanthones such as thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, 2,4-dimethylthioxanthone, and isopropylthioxanthone. 1 type (s) or 2 or more types can be used for radical photopolymerization initiators, You may use P1 types mutually, P2 types, or P1 type and P2 type together. Moreover, it is preferable to contain the photocurable composition of this invention in the ratio of 0.5 to 5 weight%.
本発明における鎖状脂肪族および脂環式単官能（メタ）アクリレートモノマー（Ｄ）は、脂肪族鎖部分の直鎖の炭素数が５〜２０のものが好ましく、８〜１６のものがより好ましい。また本発明に用いる単官能（メタ）アクリレートには水酸基やアミノ基などの極性を持った構造は適さない。極性基を持った（メタ）アクリレートを添加すると本発明成分（Ｂ）との相溶性が著しく低下するだけでなく、相溶性が得られたとしても耐溶剤性が低下する。鎖状脂肪族単官能（メタ）アクリレートモノマーとしては、具体的には、２−エチルヘキシル（メタ）アクリレート、オクチル（メタ）アクリレート、イソオクチル（メタ）アクリレート、ラウリル（メタ）アクリレート、デシル（メタ）アクリレート、ドデシル（メタ）アクリレート、ステアリル（メタ）アクリレート、ヘキサデシル（メタ）アクリレート等が例示される。また本発明で使用する脂環式（メタ）アクリレート成分の具体例としては、シクロヘキシル（メタ）アクリレート、ノルボルニル（メタ）アクリレート、ジシクロペンタニル（メタ）アクリレート、ジシクロペンテニル（メタ）アクリレート、イソボロニル（メタ）アクリレート等が挙げられる。本発明において（Ｄ）成分は必須成分ではないが、添加することによって表面硬化性が向上したり、耐溶剤性や湿度バリア性をさらに向上する効果がある。その場合その添加量は成分（Ａ）に対して８０重量部以下の割合で添加することが好ましい（より好ましくは２０〜６０重量部である）。８０重量部を超えると硬化物の柔軟性は著しく損ねてしまう。 The chain aliphatic and alicyclic monofunctional (meth) acrylate monomer (D) in the present invention preferably has 5 to 20 carbon atoms in the aliphatic chain portion, more preferably 8 to 16 carbon atoms. . Moreover, the monofunctional (meth) acrylate used in the present invention is not suitable for a structure having a polarity such as a hydroxyl group or an amino group. When (meth) acrylate having a polar group is added, not only the compatibility with the component (B) of the present invention is remarkably lowered, but also the solvent resistance is lowered even if the compatibility is obtained. Specific examples of the chain aliphatic monofunctional (meth) acrylate monomer include 2-ethylhexyl (meth) acrylate, octyl (meth) acrylate, isooctyl (meth) acrylate, lauryl (meth) acrylate, and decyl (meth) acrylate. , Dodecyl (meth) acrylate, stearyl (meth) acrylate, hexadecyl (meth) acrylate and the like. Specific examples of the alicyclic (meth) acrylate component used in the present invention include cyclohexyl (meth) acrylate, norbornyl (meth) acrylate, dicyclopentanyl (meth) acrylate, dicyclopentenyl (meth) acrylate, and isobornyl. Examples include (meth) acrylate. In the present invention, the component (D) is not an essential component, but adding it has the effect of improving surface curability and further improving solvent resistance and humidity barrier properties. In that case, the addition amount is preferably 80 parts by weight or less with respect to the component (A) (more preferably 20 to 60 parts by weight). If it exceeds 80 parts by weight, the flexibility of the cured product is significantly impaired.
本発明の光硬化性組成物には、本発明樹脂組成物の特性を損なわない範囲において他の添加剤を適量配合しても良い。他の添加剤としては、増感剤、顔料、染料などの着色剤、重合禁止剤、顔剤、消泡剤、カップリング剤、有機や無機充填剤等が例示される。 The photocurable composition of the present invention may be blended with an appropriate amount of other additives within a range that does not impair the properties of the resin composition of the present invention. Examples of other additives include sensitizers, colorants such as pigments and dyes, polymerization inhibitors, facial agents, antifoaming agents, coupling agents, organic and inorganic fillers, and the like.
本発明のシール剤組成物は、耐溶剤性、透湿バリア性、柔軟性、耐衝撃性を兼ね備えた硬化物を与えるもので、請求項１に記載される発明においては張り合わせ用途におけるシール剤へ用いた場合、ヒートサイクルによる被着材の膨張、収縮に追従でき、接着界面に生じる応力を吸収、緩和することができる。また請求項６に記載される発明においては、上述の請求項１記載の発明と類似用途への応用が可能であり、さらには硬化時における表面タック性の低減性から、ＣＩＰＧや封止剤表面がオープンとなる部位への使用が可能となる。 The sealant composition of the present invention provides a cured product having solvent resistance, moisture permeability barrier property, flexibility, and impact resistance. In the invention described in claim 1, the sealant composition is used for bonding. When used, it can follow the expansion and contraction of the adherend due to the heat cycle, and can absorb and relieve stress generated at the adhesive interface. Further, the invention described in claim 6 can be applied to similar uses as in the invention described in claim 1 above, and further, the surface of the CIPG or the sealant is reduced from the reduction of surface tackiness at the time of curing. It can be used for parts that are open.
以下に実施例によって本発明について具体的に説明するが、本発明は以下の実施例により制約されるものではない。 EXAMPLES The present invention will be specifically described below with reference to examples, but the present invention is not limited by the following examples.
末端に（メタ）アクリル基を有し主骨格を水添されたポリブタジエン骨格を持つ重合体（Ａ）としてＴＥＡＩ１０００（日本曹達社製）、ＳＰＢＤＡ（大坂有機社製）、また、成分（Ａ）の比較として、末端に（メタ）アクリル基を有するポリブタジエン骨格を持つ重合体（成分（Ａ）の未水添物、以下ＴＥＡ１０００：日本曹達社製）、ＵＥ８２００（大日本インキ社製エポキシアクリレート）、ＵＦ８００１（共栄社化学社製ウレタンアクリレート）、飽和脂肪族エラストマー（Ｂ）として水添ポリブタジエン（ＢＩ２０００：日本曹達社製）、ポリイソブチレン（以下Ｇ１０００、Ｇ３０００：ＢＡＳＦジャパン社製、ＥＰ６００Ａ：鐘淵化学社製）、成分（Ｃ）の比較として未水添ポリブタジエン（以下ＢＩ２０００：日本曹達社製）、ポリイソプレン（以下ＬＩＲ−３０：クラレ社製）、光重合開始剤（Ｃ）としてイルガキュア１８４（以下、＃１８４、チバ・スペシャルティ・ケミカルズ社製）炭素数が５以上の鎖状脂肪族および脂環式単官能（メタ）アクリレート成分（Ｄ）としてイソボロニルアクリレート（以下ＩＢＸＡ）、イソノニルアクリレート（以下ＩＮＡ）、ラウリルアクリレート（以下ＬＡ）、成分（Ｂ）の比較としてｎ−ブチルアクリレート（以下ｎ−ＢＡ）、２−ヒドロキシエチルアクリレート（以下ＨＥＭＡ）、Ｎ、Ｎ−ジメチルアミノエチルメタクリレート（以下ＤＭＭＡ）を、それぞれ表１〜３（表中に記載の配合量は重量部を意味する。）に示す通りに配合し、ミキサーを用いて５０℃で１時間攪拌して各組成物を得た。得られた各組成物を次に示す各試験方法に従い評価し、その結果を表１〜３に併せて記載した。 TEAI1000 (manufactured by Nippon Soda Co., Ltd.), SPBDA (manufactured by Osaka Organic Chemical Co., Ltd.), and component (A) as a polymer (A) having a polybutadiene skeleton having a (meth) acryl group at the terminal and hydrogenated main skeleton. As a comparison, a polymer having a polybutadiene skeleton having a (meth) acryl group at the terminal (unhydrogenated component (A), hereinafter TEA1000: manufactured by Nippon Soda Co., Ltd.), UE8200 (epoxy acrylate manufactured by Dainippon Ink Co., Ltd.), UF8001 (Urethane acrylate manufactured by Kyoeisha Chemical Co., Ltd.), hydrogenated polybutadiene (BI2000: manufactured by Nippon Soda Co., Ltd.), and polyisobutylene (hereinafter G1000, G3000: manufactured by BASF Japan, EP600A: manufactured by Kaneka Chemical Co., Ltd.) as saturated aliphatic elastomer (B) As a comparison of the component (C), unhydrogenated polybutadiene (hereinafter referred to as BI2000: manufactured by Nippon Soda Co., Ltd.) Polyisoprene (hereinafter LIR-30: manufactured by Kuraray Co., Ltd.), Irgacure 184 (hereinafter referred to as # 184, manufactured by Ciba Specialty Chemicals Co.) as a photopolymerization initiator (C) As a cyclic monofunctional (meth) acrylate component (D), isobornyl acrylate (hereinafter IBXA), isononyl acrylate (hereinafter INA), lauryl acrylate (hereinafter LA), and n-butyl acrylate (hereinafter referred to as component B) are compared. n-BA), 2-hydroxyethyl acrylate (hereinafter referred to as HEMA), N, N-dimethylaminoethyl methacrylate (hereinafter referred to as DMMA), respectively, in Tables 1 to 3 (the compounding amounts in the table mean parts by weight). And each composition was obtained by stirring at 50 ° C. for 1 hour using a mixer. Each composition obtained was evaluated according to the following test methods, and the results are also shown in Tables 1 to 3.
［相溶性試験］
相溶性の確認は実施例および比較例に基づいた各組成物を５０ｍＬガラス瓶に約２０ｇ入れ、２５℃にて２４時間放置後の分離状態を目視にて確認し、分離なしを○、分離ありを×として判定した。
[Compatibility test]
Compatibility is confirmed by putting about 20 g of each composition based on Examples and Comparative Examples into a 50 mL glass bottle and visually confirming the separation state after standing at 25 ° C. for 24 hours. Judged as x.
［硬さ試験］
樹脂硬さは実施例および比較例に基づいた各組成物約２ｇを２５φのポリキャップに入れ、紫外線を３０００ｍＪ／ｃｍ２照射して硬化させ、硬度計（デュロメーター タイプＡ）にて任意５点測定しその値の平均とした。目標値は５０以下とした。
[Hardness test]
Resin hardness was measured by arbitrarily measuring 5 points with a hardness meter (durometer type A) by putting about 2 g of each composition based on Examples and Comparative Examples into a 25φ polycap, curing by irradiating with 3000 mJ / cm 2 of ultraviolet rays. The average of these values was used. The target value was 50 or less.
［耐溶剤性試験］
実施例および比較例に基づいた各組成物約２ｇを２５φのポリキャップに入れ、紫外線を３０００ｍＪ／ｃｍ２照射して硬化させ、アセトニトリルに先の硬化物を重量測定後に浸漬させた（条件：６０℃×９６時間）。その後、硬化物を取り出し、表面を軽くワイプして重量を測定し、浸漬前との重量変化率を求めた。目標値は重量分率で±１５％以下とした。
[Solvent resistance test]
About 2 g of each composition based on Examples and Comparative Examples was placed in a 25φ polycap, cured by irradiating with 3000 mJ / cm 2 of ultraviolet rays, and the above cured product was immersed in acetonitrile after weight measurement (condition: 60 ° C x 96 hours). Thereafter, the cured product was taken out, the surface was wiped lightly, the weight was measured, and the weight change rate before immersion was determined. The target value was set to ± 15% or less by weight fraction.
［透湿度試験］
ＪＩＳ Ｚ ０２０８に基づき測定を行った（測定条件：６０℃×９５％ＲＨ）。測定膜の作成は、ポリフッ化エチレン製板上に樹脂をコーティングし（膜厚約１００ミクロン）、紫外線を３０００ｍＪ／ｃｍ２照射して硬化させたものを指定容器形状にカットし、塩化カルシウムを約１ｇ容器に入れて養生させた。測定は２４時間後の重量を基準値とし、その後経時で重量変化が飽和した時点を終点とした。目標値は８０ｇ／ｃｍ２・２４ｈとした。
[Moisture permeability test]
Measurement was performed based on JIS Z 0208 (measurement conditions: 60 ° C. × 95% RH). The measurement film is made by coating a resin on a polyfluorinated polyethylene plate (film thickness of about 100 microns), curing it by irradiating it with 3000 mJ / cm 2 of ultraviolet rays, cutting it into a specified container shape, and about calcium chloride. It was cured in a 1 g container. The measurement was based on the weight after 24 hours, and the end point was when the weight change was saturated over time. The target value was 80 g / cm 2 · 24 h.
［実施例１〜１０、比較例１〜４］
表１、２によれば、末端に（メタ）アクリル基を有する重合体の主鎖が未水添ポリブタジエンの場合には、本発明の特徴である耐溶剤性と透湿度が水添ポリブタジエンと比較していずれも十分な結果は得られない。一方、重合体主鎖がウレタンアクリレートやエポキシアクリレートの場合は成分（Ｂ）との相溶性が悪くなる。飽和脂肪族エラストマー成分が少ないと耐溶剤性が低下し、また多すぎると透湿性が低下する。また、飽和脂肪族エラストマーの主鎖が、炭素数５の繰り返し単位から構成されるポリイソプレンでは相溶性が悪くなる。
[Examples 1 to 10, Comparative Examples 1 to 4]
According to Tables 1 and 2, when the main chain of the polymer having a (meth) acryl group at the terminal is unhydrogenated polybutadiene, the solvent resistance and moisture permeability, which are the characteristics of the present invention, are compared with those of hydrogenated polybutadiene. In either case, sufficient results cannot be obtained. On the other hand, when the polymer main chain is urethane acrylate or epoxy acrylate, the compatibility with the component (B) is deteriorated. When there are few saturated aliphatic elastomer components, solvent resistance will fall, and when too much, moisture permeability will fall. In addition, the compatibility of the polyisoprene in which the main chain of the saturated aliphatic elastomer is composed of repeating units having 5 carbon atoms is poor.
［実施例３、１２〜１７、比較例５〜８］
表３によれば、炭素数が５以上の鎖状脂肪族または脂環式単官能（メタ）アクリレート成分を成分（Ａ）に対して８０重量部以上添加すると、耐溶剤性および透湿性は優れているが柔軟性が得られない。また、炭素数が５未満の（メタ）アクリレート成分を添加すると、樹脂の相溶性は悪くなり、透湿性も低下する。
[Examples 3, 12 to 17, Comparative Examples 5 to 8]
According to Table 3, when 80 parts by weight or more of a chain aliphatic or alicyclic monofunctional (meth) acrylate component having 5 or more carbon atoms is added to the component (A), the solvent resistance and moisture permeability are excellent. However, flexibility is not obtained. Moreover, when the (meth) acrylate component having less than 5 carbon atoms is added, the compatibility of the resin is deteriorated and the moisture permeability is also lowered.
本発明のシール剤組成物は、耐溶剤性、透湿バリア性、柔軟性、耐衝撃性を兼ね備えた硬化物を与えるもので、特に、耐溶剤性、透湿バリア性が要求される液晶表示素子、有機ＥＬ素子、色素増感型太陽電池、電子ペーパー、リチウムイオン電池、ポリアセン電池、オキシライド電池、キャパシタ、燃料電池などのシール材として有用である。 The sealant composition of the present invention provides a cured product having solvent resistance, moisture permeability barrier properties, flexibility, and impact resistance, and in particular, a liquid crystal display that requires solvent resistance and moisture permeability barrier properties. It is useful as a sealing material for elements, organic EL elements, dye-sensitized solar cells, electronic paper, lithium ion batteries, polyacene batteries, oxyride batteries, capacitors, fuel cells and the like.
Claims (10)
（Ｂ）飽和脂肪族エラストマー
（Ｃ）光重合開始剤
上記（Ａ）〜（Ｃ）を主成分とする光硬化性組成物。 (A) a polymer which is a polybutadiene having a (meth) acryl group at the terminal and having a hydrogenated main skeleton (B) a saturated aliphatic elastomer (C) a photopolymerization initiator The main components (A) to (C) above And a photocurable composition.
（式中、Ｒ１およびＲ２はそれぞれ独立して水素原子またはメチル基を、Ｒ３およびＲ４はそれぞれ独立して単なる連結基、酸素原子または炭素数１〜１６の置換、非置換の二価の有機基を表す。ｘ：ｙ＝０〜１００：１００〜０、ｎは１５〜１５０である。） The photocurable composition according to claim 1, wherein the polymer of the component (A) is represented by the following formula.
(Wherein R 1 and R 2 are each independently a hydrogen atom or a methyl group, and R 3 and R 4 are each independently a simple linking group, an oxygen atom, or a substituted or unsubstituted group having 1 to 16 carbon atoms. Represents an organic group having a valence of x: y = 0 to 100: 100 to 0, and n is 15 to 150.)
（Ｂ）飽和脂肪族エラストマー
（Ｃ）光重合開始剤
（Ｄ）炭素数が５以上の鎖状脂肪族または脂環式単官能（メタ）アクリレート
上記（Ａ）〜（Ｄ）を主成分とする光硬化性組成物。 (A) Polymer having terminal (meth) acrylic group and hydrogenated main skeleton (B) Saturated aliphatic elastomer (C) Photopolymerization initiator (D) Chain having 5 or more carbon atoms Aliphatic or alicyclic monofunctional (meth) acrylate A photocurable composition mainly comprising the above (A) to (D).
（式中、Ｒ１およびＲ２はそれぞれ独立して水素原子またはメチル基を、Ｒ３およびＲ４はそれぞれ独立して単なる連結基、酸素原子または炭素数１〜１６の置換、非置換の二価の有機基を表す。ｘ：ｙ＝０〜１００：１００〜０、ｎは１５〜１５０である。） The photocurable composition according to claim 6, wherein the polymer of component (A) is represented by the following formula.
(Wherein R 1 and R 2 are each independently a hydrogen atom or a methyl group, and R 3 and R 4 are each independently a simple linking group, an oxygen atom, or a substituted or unsubstituted group having 1 to 16 carbon atoms. Represents an organic group having a valence of x: y = 0 to 100: 100 to 0, and n is 15 to 150.)
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| PCT/JP2005/012170 WO2006001522A1 (en) | 2004-06-25 | 2005-06-24 | Photocurable composition |
| KR1020067026613A KR20070039880A (en) | 2004-06-25 | 2005-06-24 | Photocurable composition |
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