CN102473432A - Ultraviolet-curable resin composition for use in optical disks and cured products thereof - Google Patents
Ultraviolet-curable resin composition for use in optical disks and cured products thereof Download PDFInfo
- Publication number
- CN102473432A CN102473432A CN2010800317632A CN201080031763A CN102473432A CN 102473432 A CN102473432 A CN 102473432A CN 2010800317632 A CN2010800317632 A CN 2010800317632A CN 201080031763 A CN201080031763 A CN 201080031763A CN 102473432 A CN102473432 A CN 102473432A
- Authority
- CN
- China
- Prior art keywords
- methyl
- ester
- composition
- ultraviolet
- acrylic acid
- 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.)
- Pending
Links
- 239000011342 resin composition Substances 0.000 title claims abstract description 54
- 230000003287 optical effect Effects 0.000 title claims abstract description 39
- 229920005989 resin Polymers 0.000 claims abstract description 127
- 239000011347 resin Substances 0.000 claims abstract description 127
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 40
- 239000000178 monomer Substances 0.000 claims abstract description 23
- -1 acrylic ester Chemical class 0.000 claims description 164
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 88
- 239000000203 mixture Substances 0.000 claims description 86
- CERQOIWHTDAKMF-UHFFFAOYSA-N alpha-methacrylic acid Natural products CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 51
- 239000000463 material Substances 0.000 claims description 30
- 238000012986 modification Methods 0.000 claims description 22
- 230000004048 modification Effects 0.000 claims description 22
- 239000004593 Epoxy Substances 0.000 claims description 18
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 16
- 239000012948 isocyanate Substances 0.000 claims description 14
- 150000002513 isocyanates Chemical class 0.000 claims description 14
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 13
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 11
- RJWUMFHQJJBBOD-UHFFFAOYSA-N isooctadecane Natural products CCCCCCCCCCCCCCCC(C)C RJWUMFHQJJBBOD-UHFFFAOYSA-N 0.000 claims description 11
- 229940043268 2,2,4,4,6,8,8-heptamethylnonane Drugs 0.000 claims description 9
- BANXPJUEBPWEOT-UHFFFAOYSA-N isohexadecane Natural products CCCCCCCCCCCCCC(C)C BANXPJUEBPWEOT-UHFFFAOYSA-N 0.000 claims description 9
- KUVMKLCGXIYSNH-UHFFFAOYSA-N isopentadecane Natural products CCCCCCCCCCCCC(C)C KUVMKLCGXIYSNH-UHFFFAOYSA-N 0.000 claims description 9
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- HOWGUJZVBDQJKV-UHFFFAOYSA-N n-propyl-nonadecane Natural products CCCCCCCCCCCCCCCCCCCCCC HOWGUJZVBDQJKV-UHFFFAOYSA-N 0.000 claims description 7
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 7
- BXGYYDRIMBPOMN-UHFFFAOYSA-N 2-(hydroxymethoxy)ethoxymethanol Chemical compound OCOCCOCO BXGYYDRIMBPOMN-UHFFFAOYSA-N 0.000 claims description 6
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 6
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 6
- LVGFPWDANALGOY-UHFFFAOYSA-N 8-methylnonyl prop-2-enoate Chemical compound CC(C)CCCCCCCOC(=O)C=C LVGFPWDANALGOY-UHFFFAOYSA-N 0.000 claims description 5
- 125000005442 diisocyanate group Chemical group 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 5
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 claims description 4
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 claims description 3
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 3
- 235000010290 biphenyl Nutrition 0.000 claims description 3
- 239000004305 biphenyl Substances 0.000 claims description 3
- 125000006267 biphenyl group Chemical group 0.000 claims description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 3
- 230000005855 radiation Effects 0.000 claims description 3
- 238000000034 method Methods 0.000 abstract description 22
- 239000000758 substrate Substances 0.000 abstract description 20
- 230000015572 biosynthetic process Effects 0.000 abstract description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 abstract 5
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 abstract 1
- 239000003999 initiator Substances 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 86
- 238000003825 pressing Methods 0.000 description 35
- 238000000576 coating method Methods 0.000 description 28
- 239000011248 coating agent Substances 0.000 description 27
- 229920000647 polyepoxide Polymers 0.000 description 21
- 239000003822 epoxy resin Substances 0.000 description 20
- 239000003795 chemical substances by application Substances 0.000 description 17
- 229920000515 polycarbonate Polymers 0.000 description 16
- 239000004417 polycarbonate Substances 0.000 description 16
- 239000012790 adhesive layer Substances 0.000 description 15
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 10
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 9
- 238000010023 transfer printing Methods 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 239000012752 auxiliary agent Substances 0.000 description 5
- 229940106691 bisphenol a Drugs 0.000 description 5
- 229940117969 neopentyl glycol Drugs 0.000 description 5
- 229920005668 polycarbonate resin Polymers 0.000 description 5
- 239000004431 polycarbonate resin Substances 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- FVCSARBUZVPSQF-UHFFFAOYSA-N 5-(2,4-dioxooxolan-3-yl)-7-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C(C(OC2=O)=O)C2C(C)=CC1C1C(=O)COC1=O FVCSARBUZVPSQF-UHFFFAOYSA-N 0.000 description 4
- 229910001316 Ag alloy Inorganic materials 0.000 description 4
- 229930185605 Bisphenol Natural products 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 239000000853 adhesive Substances 0.000 description 4
- 230000001070 adhesive effect Effects 0.000 description 4
- 229920000098 polyolefin Polymers 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 3
- TUOBEAZXHLTYLF-UHFFFAOYSA-N [2-(hydroxymethyl)-2-(prop-2-enoyloxymethyl)butyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(CC)COC(=O)C=C TUOBEAZXHLTYLF-UHFFFAOYSA-N 0.000 description 3
- 239000002671 adjuvant Substances 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 230000002950 deficient Effects 0.000 description 3
- 150000002118 epoxides Chemical class 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229920001021 polysulfide Polymers 0.000 description 3
- 239000005077 polysulfide Substances 0.000 description 3
- 150000008117 polysulfides Polymers 0.000 description 3
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 239000006087 Silane Coupling Agent Substances 0.000 description 2
- 238000004026 adhesive bonding Methods 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 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 2
- 239000004841 bisphenol A epoxy resin Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical class OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 239000000113 methacrylic resin Substances 0.000 description 2
- OTRIMLCPYJAPPD-UHFFFAOYSA-N methanol prop-2-enoic acid Chemical compound OC.OC.OC(=O)C=C.OC(=O)C=C OTRIMLCPYJAPPD-UHFFFAOYSA-N 0.000 description 2
- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 description 2
- 238000005457 optimization Methods 0.000 description 2
- 239000012860 organic pigment Substances 0.000 description 2
- 230000002093 peripheral effect Effects 0.000 description 2
- 239000012782 phase change material Substances 0.000 description 2
- 229920001225 polyester resin Polymers 0.000 description 2
- 239000004645 polyester resin Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229920005672 polyolefin resin Polymers 0.000 description 2
- 229920005990 polystyrene resin Polymers 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 238000013517 stratification Methods 0.000 description 2
- 210000001745 uvea Anatomy 0.000 description 2
- PWCBSPFFLHCDKT-UHFFFAOYSA-N (2,6-dimethoxyphenyl)-(2,4,4-trimethylpentylphosphonoyl)methanone Chemical compound COC1=CC=CC(OC)=C1C(=O)P(=O)CC(C)CC(C)(C)C PWCBSPFFLHCDKT-UHFFFAOYSA-N 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
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 1
- KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 description 1
- UMLWXYJZDNNBTD-UHFFFAOYSA-N 2-(dimethylamino)-1-phenylethanone Chemical compound CN(C)CC(=O)C1=CC=CC=C1 UMLWXYJZDNNBTD-UHFFFAOYSA-N 0.000 description 1
- KJSGODDTWRXQRH-UHFFFAOYSA-N 2-(dimethylamino)ethyl benzoate Chemical compound CN(C)CCOC(=O)C1=CC=CC=C1 KJSGODDTWRXQRH-UHFFFAOYSA-N 0.000 description 1
- SEFYJVFBMNOLBK-UHFFFAOYSA-N 2-[2-[2-(oxiran-2-ylmethoxy)ethoxy]ethoxymethyl]oxirane Chemical compound C1OC1COCCOCCOCC1CO1 SEFYJVFBMNOLBK-UHFFFAOYSA-N 0.000 description 1
- SHKUUQIDMUMQQK-UHFFFAOYSA-N 2-[4-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COCCCCOCC1CO1 SHKUUQIDMUMQQK-UHFFFAOYSA-N 0.000 description 1
- WTYYGFLRBWMFRY-UHFFFAOYSA-N 2-[6-(oxiran-2-ylmethoxy)hexoxymethyl]oxirane Chemical compound C1OC1COCCCCCCOCC1CO1 WTYYGFLRBWMFRY-UHFFFAOYSA-N 0.000 description 1
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 1
- UKQBWWAPJNHIQR-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical class OC(=O)C=C.CCC(CO)(CO)CO UKQBWWAPJNHIQR-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
- IKYAJDOSWUATPI-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propane-1-thiol Chemical compound CO[Si](C)(OC)CCCS IKYAJDOSWUATPI-UHFFFAOYSA-N 0.000 description 1
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
- OFSAUHSCHWRZKM-UHFFFAOYSA-N Padimate A Chemical compound CC(C)CCOC(=O)C1=CC=C(N(C)C)C=C1 OFSAUHSCHWRZKM-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910052771 Terbium Inorganic materials 0.000 description 1
- SSOONFBDIYMPEU-UHFFFAOYSA-N [3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propyl] prop-2-enoate Chemical compound OCC(CO)(CO)COCC(CO)(CO)COC(=O)C=C SSOONFBDIYMPEU-UHFFFAOYSA-N 0.000 description 1
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical class C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000010538 cationic polymerization reaction Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- UPBRZMAXCHYTQT-UHFFFAOYSA-N cyclopenta-1,3-diene;prop-2-enoic acid Chemical compound C1C=CC=C1.C1C=CC=C1.OC(=O)C=C UPBRZMAXCHYTQT-UHFFFAOYSA-N 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- PODOEQVNFJSWIK-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethoxyphenyl)methanone Chemical compound COC1=CC(OC)=CC(OC)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 PODOEQVNFJSWIK-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 150000002148 esters Chemical group 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 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
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- WKGDNXBDNLZSKC-UHFFFAOYSA-N oxido(phenyl)phosphanium Chemical compound O=[PH2]c1ccccc1 WKGDNXBDNLZSKC-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
- G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
- G11B7/252—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers
- G11B7/253—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates
- G11B7/2533—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates comprising resins
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- 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
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
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- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
- G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
- G11B7/252—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers
- G11B7/256—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of layers improving adhesion between layers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
- C08F220/343—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate in the form of urethane links
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- 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)
- Optical Record Carriers And Manufacture Thereof (AREA)
- Polymerisation Methods In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polyurethanes Or Polyureas (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
An ultraviolet-curable resin composition characterized by comprising (A) a (meth)acrylate having an aliphatic chain, particularly a C10-25 aliphatic chain, either (B) a (meth)acrylate monomer exclusive of the (meth)acrylate (A) and the following (meth)acrylate (C) and/or (C) a urethane (meth)acrylate, and (D) a photopolymerization initiator. The ultraviolet-curable resin composition is suitable for use in the intermediate resin layer of a multilayer optical disk, and ensures high mass productivity in the formation of substrates by the 2P method. Further, the ultraviolet-curable resin composition exhibits excellent peelability from a stamper, and can provide an optical disk base which exhibits a reduced change of warpage when curing or after the resulting multilayer disk is placed under high-temperature and high-humidity conditions.
Description
Technical field
The present invention relates to the purposes (especially for the purposes of middle resin layer) that a kind of ultraviolet-curing resin composition, said composition be used for multiplayer optical disk, CD with cured layer of this resin combination; Be particularly related to the resin combination that is used for producing efficiently high density multilayered optical disk of future generation; It is high that this multiplayer optical disk is neutralized the fissility that mould (mould that CD is used) peels off from polycarbonate, and the warpage when solidifying, high temperature how the variation of the warpage under the wet condition is little.
Background technology
In recent years, the high capacity of CD progress is remarkable, and in order to increase memory capacity, the multi-layered type CD is popularized rapidly.Improve the technology of video disc recording capacity, can enumerate: high NA (opening number) change of the object lens of the short wavelengthization of recording/copying light beam, recording/copying light beam irradiates optical system, the multiple stratification of recording layer etc.Wherein,, compare with high NAization with the short wavelengthization based on the high capacity of the multiple stratification of recording layer, can be with the implemented with low cost high capacity.
For example, in having the DVD CD of two-layer recording layer, form two-layer recording layer and carry out range upon range of structure across transparent resin middle layer (below be also referred to as transparent middle resin layer).Particularly, be the structure of second transparent resin substrate of first transparent resin substrate that stacks gradually 0.6mm, first recording layer, the first semitransparent reflector rete, adhesive layer, transparent resin middle layer, second recording layer, second reflective coating, adhesive layer, 0.6mm.The formation method in the transparent resin middle layer of this moment; For example can enumerate: will be placed on the adhesive layer that forms on the first semitransparent reflector rete in order to the ultraviolet-curing resin composition that forms the transparent resin middle layer; The guiding that will have a recording/copying light beam is carried side placed on it with the transparent resin pressing mold of relief patterns such as guide channel; Be rotated coating, formed ultraviolet-curing resin composition layer is solidified after, pressing mold is peeled off; With the concavo-convex surface that is transferred to ultraviolet-curing resin composition, and the method in formation transparent resin middle layer; Perhaps; After being formed at the solidfied material layer of said resin combination on the pressing mold; To carry with the pressing mold of this solidfied material layer and be placed at the adhesive layer placed on the first semitransparent reflector rete and form with on the resin, form adhesive layer through rotary coating after, this adhesive layer is solidified; Then this pressing mold is peeled off from the solidfied material layer of said resin combination, and the method (transfer printing) in formation transparent resin middle layer.
In the Blu-ray Disc; Read-only optical disc is the recording figure forming of transfer printing pit shape on as the single face of the polycarbonate substrate of the for example diameter 120mm of substrate, thickness 1.1mm; Surface at this substrate forms first reflective coating as first recording layer, for example silver alloy reflective layer.In addition, on first reflective coating, form the transparent resin middle layer that transfer printing has the recording figure forming of pit shape, go up second reflective coating that forms as second recording layer, for example silver alloy reflective layer in this transparent resin middle layer (intermediate coat) across adhesive layer.Be formed on the formation of this reflective coating laminated transparent resin layer then.In addition, the silver alloy reflective layer carries out film forming in a vacuum through for example sputtering method method is proposed.
Recording type optical disc for example is formed on surperficial laminated first reflective coating, first dielectric layer, first recording layer, second dielectric layer of substrate that transfer printing on the single face of polycarbonate substrate of diameter 120mm, thickness 1.1mm has the recording figure forming of pit shape, and then on second dielectric layer, stacks gradually the structure of transparent resin middle layer, second reflective coating, the 3rd dielectric layer, second recording layer, the 4th dielectric layer and transparent resin layer across adhesive layer.
At this moment; The ultraviolet-curing resin composition that will be used to form the transparent resin middle layer across adhesive layer is coated on reflective coating or the dielectric layer; And by being pressed on the transparent resin pressing mold of guiding with recording/copying light beam with relief patterns such as guide channels; After ultraviolet-curing resin composition is solidified, pressing mold is peeled off, be transferred to the surface of ultraviolet-curing resin composition and form recording type optical disc (transfer printing) concavo-convex.
At this, in read-only optical disc, the transparent resin middle layer forms second reflective coating usually on its male and fomale(M&F), and opposing face is then gluing across the adhesive layer and first reflective coating.In addition, in recording type optical disc, this transparent resin middle layer forms second reflective coating usually on its male and fomale(M&F), and opposing face is then gluing across the adhesive layer and second dielectric layer.
Generally speaking, this transfer printing is called 2P (Photo Polymerization; Photopolymerization) method, employed ultraviolet-curing resin composition is called the 2P agent.
The transparent resin that the transparent resin pressing mold is used can be enumerated: acrylic resin, methacrylic resin, polycarbonate resin, polyolefin resin (particularly noncrystalline polyolefin), polyester resin, polystyrene resin, epoxy resin etc.Wherein, viewpoints such as the fissility after the 2P agent is solidified, agent of low hygroscopicity, shape stability consider that preferred noncrystalline polyolefin is considered from the viewpoint of material cost, the optimization polycarbonate resin.Therefore; For cutting down cost; The method of the optical recording media (multi-layered optical recording medium) that a kind of manufacturing has several record layers is proposed; Even this manufacturing approach uses cheap polycarbonate to neutralize mould, its fissility might as well and make yield rate improve, and has also developed the resin (patent documentation 1) that is suitable for this manufacturing approach.
At present, the main flow of the ultraviolet-curing resin composition during as use 2P method for example can be enumerated: the composition that (a) contains prepolymer, monomer and the Photoepolymerizationinitiater initiater that can carry out the optical free radical polymerization; (b) contain the composition of prepolymer, monomer and the Photoepolymerizationinitiater initiater that can carry out the light cationic polymerization; (c) be mixed with the composition etc. of optical free radical polymerism and cationically polymerizable composition.
Prepolymer can be enumerated: various epoxy radicals (methyl) acrylic ester ((methyl) acryloyl group of addition in the epoxy skeleton and obtain material) is ((methyl) acryloyl group of addition in the carbamate skeleton and obtain material) etc. or/and carbamate (methyl) acrylic ester.These compositions, appreciable impact is from the such mouldability of the release property of the pressing mold demoulding respectively; And to the desired characteristic of the such CD of tackiness, moisture-proof, the flexibility of reflective coating or dielectric layer.
The general use of monomer has the monomer of (methyl) acryloyl group as functional group.In addition, also can use monomer with vinyl.Generally speaking, the viscosity of prepolymer is high, is difficult to separately use as the 2P agent, therefore uses monomer as reactive diluent.For example, through using the above monomer of 3 officials ability, the cross-linking density of solidfied material is increased, and improve hardness, Young modulus, humidity resistance.
When making multiplayer optical disk, during from fissility difference that the transparent resin pressing mold is peeled off, can produce the part in transparent resin middle layer and the defective that the transparent resin pressing mold is together peeled off.During transfer printing property difference, can produce mistake during recording/copying.When warpage is big after the ultraviolet curing, can't recording layer or reflective coating be formed uniformly on formed relief pattern, when perhaps being DVD, second substrate of can't fitting when perhaps being Blu-ray Disc, can't be formed uniformly the light-transmitting layer of 0.1mm.In addition, when relief pattern produced distortion under high temperature wets condition more, the recording characteristic of first and second recording layer (for example jittering characteristic) can't reach equal.
The 2P agent that patent documentation 2 to 5 is put down in writing uses metal pressing mold on the layer that is formed on the glass substrate, to form relief pattern.In addition, various 2P agent have also been put down in writing in the patent documentation 6 to 10.
The prior art document
Patent documentation
Patent documentation 1: TOHKEMY 2007-224057 communique
Patent documentation 2: japanese kokai publication hei 5-59139 communique
Patent documentation 3: japanese kokai publication hei 5-132534 communique
Patent documentation 4: japanese kokai publication hei 5-140254 communique
Patent documentation 5: japanese kokai publication hei 5-132506 communique
Patent documentation 6: TOHKEMY 2003-331463 communique
Patent documentation 7: TOHKEMY 2004-288242 communique
Patent documentation 8: TOHKEMY 2004-288264 communique
Patent documentation 9: TOHKEMY 2005-332564 communique
Patent documentation 10: No. the 4193916th, Jap.P.
Summary of the invention
Usually, the ultraviolet curing resin as the 2P agent is used behind pressing mold formation relief pattern, need be easy to peel off (fissility of peeling off from pressing mold is high) from pressing mold under the state that keeps this pattern.At this moment, be difficult to when pressing mold is peeled off, resin can produce the defective of resin bed or the defective of relief pattern etc. attached on the pressing mold, and the formation of reflectance coating or dielectric layer is had problems, thereby causes production efficiency to reduce.In addition, even how wet the high resin of the fissility of peeling off from pressing mold be placed on high temperature condition following time when ultraviolet curing or with multiplayer optical disk,, then can cause problems such as producing read error if the warpage variable quantity is big.
Therefore, in view of said circumstances, the objective of the invention is to; Have (methyl) acrylic ester of aliphatic chain through use, particularly have (methyl) acrylic ester of specific aliphatic chain, a kind of resin combination is provided; This resin combination is peeled off from pressing mold; It is good particularly to neutralize peeling off of mould from polycarbonate, and when the curing of formed resin bed and the multiplayer optical disk that will have this solidfied material layer be placed on high temperature how under the wet condition after, the warpage variable quantity is also little.
In addition; Resin combination of the present invention; Owing to directly be adhesive in through curing on the arbitrary layer in reflectance coating or the dielectric layer, therefore, need not to be provided with earlier and again pressing mold is peeled off after adhesive layer is adhesive in curing resin layer on reflectance coating or the dielectric layer when pressing mold is peeled off.That is, directly resin bed is formed on the arbitrary layer in reflectance coating or the dielectric layer, and forms concavo-convex and/or be cured, can easily directly pressing mold be peeled off thus through pressing mold.Therefore, can omit the lip-deep adhesive layer that is used for the solidfied material layer of the ultraviolet-curing resin composition that uses as the 2P agent is adhesive in reflectance coating or dielectric layer.
The inventor has (methyl) acrylic ester of aliphatic chain through use; (methyl) acrylic ester that particularly has specific aliphatic chain; Found to make and neutralized the fissility that mould peels off from pressing mold, particularly polycarbonate and improve, and when solidifying and with multiplayer optical disk, be placed on high temperature how under the wet condition the little resin of back warpage variable quantity form.Develop a kind of ultraviolet-curing resin composition thus, it is good that this resin combination is neutralized the fissility that mould peels off from polycarbonate, and when solidifying and with multiplayer optical disk, be placed on high temperature how under the wet condition after, the warpage variable quantity is also little.
The present invention relates to following (1) to (12).
(1) a kind of multiplayer optical disk is used ultraviolet-curing resin composition; It is characterized in that, contain: (methyl) acrylic ester, (B) (methyl) acrylate monomer and/or (C) carbamate (methyl) acrylic ester and (D) Photoepolymerizationinitiater initiater that (A) have aliphatic chain.
(2) use ultraviolet-curing resin composition like (1) described multiplayer optical disk; Wherein, (methyl) acrylic ester that (A) has an aliphatic chain comprise for being selected from the group of (methyl) acrylic acid dodecane ester, (methyl) acrylic acid octadecane ester, (methyl) acrylic acid hexadecane ester, (methyl) acrylic acid docosane ester, (methyl) acrylic acid Permethyl 99A ester, (methyl) acrylic acid isooctadecane ester, (methyl) acrylic acid isohexadecane ester and the different docosane ester of (methyl) acrylic acid more than a kind or 2 kinds.
(3) use ultraviolet-curing resin composition like (1) or (2) described multiplayer optical disk; Wherein, (B) (methyl) acrylate monomer comprise for being selected from the group of trimethylolpropane two (methyl) acrylic ester of neopentyl glycol two (methyl) acrylic ester, tristane dimethanol two (methyl) acrylic ester and hydroxy pivalin aldehyde modification of (methyl) IBOA, epoxy pronane modification more than a kind or 2 kinds.
(4) use ultraviolet-curing resin composition like each described multiplayer optical disk in (1) to (3); Wherein, whole with respect to resin combination, (A) composition is 5 to 90 weight %; (B) composition and/or (C) composition be 5 to 90 weight %, (D) composition is 1 to 15 weight %.
(5) a kind of CD, it has the solidfied material that each described resin combination irradiation ultraviolet radiation in said (1) to (4) is obtained.
(6) a kind of ultraviolet-curing resin composition, it contains: (methyl) acrylic ester of (A) representing with aliphatic chain by following formula (1),
In the formula, R representes H or CH
3, n representes 10 to 25 integer; And
(B) be selected from least a (methyl) acrylate monomer in the group of trimethylolpropane two (methyl) acrylic ester of neopentyl glycol two (methyl) acrylic ester, tristane dimethanol two (methyl) acrylic ester and the hydroxy pivalin aldehyde modification that comprise (methyl) IBOA, epoxy pronane modification; Perhaps carbamate (methyl) acrylic ester that obtains of (C) reaction through organic multiple isocyanate and hydroxyl (methyl) acrylate compounds; And
(D) Photoepolymerizationinitiater initiater, and,
With respect to the total amount of resin combination,
(i) (A) composition is 5 to 90 weight %,
(ii) (B) composition or (C) composition perhaps (B) and (C) the two is 5 to 90 weight %, (A) total amount to (C) composition is 85 to 99 weight %,
(iii) (D) composition is 1 to 15 weight %.
(7) like (6) described ultraviolet-curing resin composition, wherein, the aliphatic chain with (methyl) acrylic ester of aliphatic chain is the aliphatic chain with side chain.
(8) like (7) described ultraviolet-curing resin composition; Wherein, (methyl) acrylic ester that has an aliphatic chain is for being selected from least a in the group that comprises isodecyl acrylate, (methyl) acrylic acid Permethyl 99A ester, (methyl) acrylic acid isooctadecane ester, (methyl) acrylic acid isohexadecane ester and the different docosane ester of (methyl) acrylic acid.
(9) like each described ultraviolet-curing resin composition in above-mentioned (6) to (8); Wherein, Organic multiple isocyanate comprises IPDI, 1 for being selected from; Hexamethylene-diisocyanate, toluene diisocyanate, XDI and diphenyl methane-4,4 '-at least a diisocyanate in the group of diisocyanate, perhaps tetrahydrochysene dicyclopentadiene based isocyanate.
(10) like each described ultraviolet-curing resin composition in above-mentioned (6) to (9), wherein, hydroxyl (methyl) acrylate compounds is substituted C2 to the C10 aliphatics of hydroxyl (methyl) acrylic ester.
(11) purposes of each described ultraviolet-curing resin composition in above-mentioned (6) to (10), it is used for the middle resin layer of multiplayer optical disk.
(12) a kind of multiplayer optical disk, it has the solidfied material layer of each described ultraviolet-curing resin composition in above-mentioned (6) to (10).
The invention effect
Ultraviolet-curing resin composition of the present invention and solidfied material thereof; Useful as the 2P agent; This 2P agent peeling off from pressing mold; Particularly neutralize the fissility good (peel strength of peeling off from pressing mold is low) that mould peels off from polycarbonate, and the warpage variable quantity before and after when solidifying and the multiplayer optical disk that will have this solidfied material layer how wet be placed on high temperature condition following time its warpage variable quantity before and after placing all little.In addition, ultraviolet-curing resin composition of the present invention can omit adhesive layer and forms middle resin layer with single component (1 liquid).In addition, can through (A) composition with (B) composition or/and (C) combination of composition come suitably to regulate viscosity, thereby can form the middle resin layer of multiplayer optical disk efficiently.
Embodiment
The present invention relates to a kind of multiplayer optical disk and use ultraviolet-curing resin composition; It is characterized in that, contain: (i) (A) has (methyl) acrylic ester of aliphatic chain, (ii) (B) (methyl) acrylate monomer and/or (C) carbamate (methyl) acrylic ester and (iii) (D) Photoepolymerizationinitiater initiater.
In addition, among the present invention, " (methyl) acrylic ester " such term, identical with general use, use with any one in acrylic ester or methacrylate or the implication of the two.
In addition, among the present invention, % or part etc. if do not specify, are then represented weight % or weight portion.In addition, ultraviolet-curing resin composition of the present invention also is recited as " resin combination of the present invention " briefly.
In the resin combination of the present invention, (methyl) acrylic ester that use (A) has aliphatic chain is as neccessary composition.Aliphatic chain with (methyl) acrylic ester of aliphatic chain, the aliphatic chain of preferred C10 to C25, more preferably shown in the following formula (1)-C
nH
2n+1The alkyl of the C10 to C25 of (n is 10 to 25 integer) expression.Therefore, has (methyl) acrylic ester of aliphatic chain, (methyl) acrylic ester of preferably representing by following formula (1).
(in the formula, R representes H or CH
3, n representes 10 to 25 integer).
Concrete example for example can be enumerated: (methyl) acrylic acid dodecane ester, (methyl) acrylic acid octadecane ester, (methyl) acrylic acid hexadecane ester, (methyl) acrylic acid docosane ester, (methyl) acrylic acid Permethyl 99A ester, (methyl) acrylic acid isooctadecane ester, (methyl) acrylic acid isohexadecane ester and the different docosane ester of (methyl) acrylic acid etc.
Viewpoint such as peel off from pressing mold from side chain more easily than straight chain and consider that the aliphatic chain with (methyl) acrylic ester of aliphatic chain preferably has (methyl) acrylic ester of side chain aliphatic chain.(methyl) acrylic ester that more preferably has the branched chain of C10 to C25.Therefore, in the above-mentioned concrete example, more preferably (methyl) acrylic acid Permethyl 99A ester, (methyl) acrylic acid isooctadecane ester, (methyl) acrylic acid isohexadecane ester or the different docosane ester of (methyl) acrylic acid.
(A) has the content of aliphatic chain (methyl) acrylic ester in the composition, is about 5 to about 90 weight % with respect to the total amount (all) of resin combination, and preferred about 10 to about 80 weight %.Though this content is because with (B) of make up use or (C) composition change and can't lumping together; But according to circumstances, be preferably about 5 to about 50 weight %, more preferably from about 5 to about 40 weight %; Further preferred about 10 to about 40 weight %, and most preferably from about 10 to about 30 weight %.
(A) have the commercially available article of (methyl) acrylic ester of aliphatic chain, for example can enumerate: day oiling is learned Blemmer SA, Blemmer CA, the Blemmer VA of corporate system; The acrylic acid isooctadecane ester of Xin Zhong village chemical industrial company system; The Light-Acrylate IS-A of chemical company of common prosperity society system, Light-Acrylate IM-A etc.
Use (B) (methyl) acrylate monomer in the resin combination of the present invention.Employed (methyl) acrylate monomer is not so long as (A) composition and (C) known (methyl) acrylate monomer beyond the composition then can have especially restrictedly and use.Example can be enumerated: tristane (methyl) acrylic ester; (methyl) benzyl acrylate; Tetrahydrochysene dicyclopentadiene base (methyl) acrylic ester; (methyl) IBOA; (methyl) acrylic acid diamantane ester; (methyl) benzyl acrylate; (methyl) tetrahydrofurfuryl acrylate; Morpholine (methyl) acrylic ester; Neopentyl glycol two (methyl) acrylic ester of epoxy pronane modification; Tristane dimethanol two (methyl) acrylic ester; Trimethylolpropane two (methyl) acrylic ester of hydroxy pivalin aldehyde modification; Hydroxy new pentane acid neopentyl glycol two (methyl) acrylic ester etc.
In order to improve fissility etc. through using with said (A) composition combination, (methyl) acrylate monomer preferably uses at least a in the group of the trimethylolpropane diacrylate that is selected from the neopentylglycol diacrylate, tristane dimethanol diacrylate and the hydroxy pivalin aldehyde modification that comprise IBOA, epoxy pronane modification.
These monomers can obtain the resin combination of the present invention that peel strength is low and the warpage variable quantity is also few through using with (methyl) acrylic ester combination with side chain aliphatic chain as said (A) composition.Wherein, more preferably (methyl) IBOA is or/and the trimethylolpropane diacrylate of hydroxy pivalin aldehyde modification, and further preferred the two combination is used.
(C) carbamate (methyl) acrylic ester that uses in the resin combination of the present invention; Can be used to replace said (B) composition and contained (A) composition and (C) composition do not contain (B) composition as resinous principle resin combination, but usually should (C) composition use with (B) composition combination.
(C) composition carbamate (methyl) acrylic ester is preferably through making organic polyisocyanate compound and hydroxyl (methyl) acrylate compounds react the compound that obtains.
Organic multiple isocyanate; For example can enumerate: IPDI, 1; Hexamethylene-diisocyanate, toluene diisocyanate, XDI and diphenyl methane-4; 4 '-diisocyanates such as diisocyanate, perhaps isocyanates such as tetrahydrochysene dicyclopentadiene based isocyanate.
Wherein, more preferably IPDI or toluene diisocyanate.
Hydroxyl (methyl) acrylate compounds for example can be enumerated: substituted C2 to C10 aliphatics (methyl) acrylic ester of hydroxyl or hydroxyl caprolactone (methyl) acrylic ester etc.Substituted C2 to the C10 aliphatics of hydroxyl (methyl) acrylic ester; Particularly, can enumerate preferably: (methyl) hydroxy-ethyl acrylate, (methyl) hydroxypropyl acrylate, (methyl) acrylic acid hydroxy butyl ester, dihydroxymethyl cyclohexyl list (methyl) acrylic ester, pentaerythrite three (methyl) acrylic ester, dipentaerythritol five (methyl) acrylic ester etc.
Wherein, preferred material can be enumerated: (methyl) hydroxy-ethyl acrylate, (methyl) hydroxypropyl acrylate, (methyl) acrylic acid hydroxy butyl ester, pentaerythrite three (methyl) acrylic ester etc.
Therefore; Preferred carbamate (methyl) acrylic ester can be enumerated carbamate (methyl) acrylic ester that the reaction through above-mentioned organic multiple isocyanate and substituted C2 to C10 aliphatics (methyl) acrylic ester of above-mentioned hydroxyl or hydroxyl caprolactone (methyl) acrylic ester obtains.In addition; Preferred carbamate (methyl) acrylic ester, can enumerate the IPDI enumerated through the preferred organic multiple isocyanate of above-mentioned conduct or toluene diisocyanate, with above-mentioned preferred compound and carbamate (methyl) acrylic ester that the reaction of illustrative compound obtains as hydroxyl (methyl) acrylic ester.
Reaction is carried out through following manner.Promptly; Be preferably the mode of 1.0 to 2.1 equivalents with hydroxyl with respect to isocyanate group 1.0 equivalent hydroxyl (methyl) acrylic ester of organic multiple isocyanate; Organic multiple isocyanate is mixed with hydroxyl (methyl) acrylate compounds; Under 70 to 90 ℃, react, and obtain target carbamate (methyl) acrylic ester.
Above-mentioned carbamate (methyl) acrylic ester, can use a kind or with arbitrary proportion mix 2 kinds with on use.
(B) (methyl) acrylate monomer or (C) at least a content of carbamate (methyl) acrylic ester in the resin combination of the present invention count about 5 to about 90%, preferred about 10 to about 80% with the ratio (weight) with respect to the total amount of this resin combination.In addition, preferred range according to circumstances is 50 to 90%, more preferably 60 to 85%.
In addition, (A),, then can be any range as long as can reach the scope of effect of the present invention to the total amount of (C) composition content ratio with respect to the total amount of resin combination of the present invention.Usually the fissility that the viscosity, solidfied material layer of considering resin combination is peeled off from pressing mold and the luminous transparency of solidfied material layer, have warpage and the permanance etc. of the CD of this solidfied material layer; Total amount with respect to this resin combination; (A) to the total amount of (C) composition; Be preferably and contain 50% at least, more preferably contain 70% at least.(A) to the total amount of (C) composition total amount, further be preferably 85 to 99%, most preferably 90 to 99% with respect to this resin combination.
In the above-mentioned situation; (A) ratio of composition and other composition ((B) composition with (C) composition), with respect to 1 part of (A) composition, other composition ((B) composition or (C) composition; Perhaps contain (B) and (C) the two the time be the two total amount); Be generally about 1 to about 20 parts, preferred about 2 to about 10 parts, further preferred about 3 to about 7 parts ratio.
(B) composition or (C) composition usually as long as in this resin combination, contain arbitrarily one at least, just can not throw into question.Therefore, with respect to the total amount of two compositions, can be that arbitrary side is 100% and the opposing party is 0%.Usually, with respect to the total amount of two compositions, (B) composition is 30 to 100%, more preferably 50 to 100%, and further preferred 70 to 100%, (C) composition is preferred 0 to 70%, and more preferably 0 to 50%, further preferred 0 to 30%.
In addition, among the present invention, can suitably contain epoxy radicals (methyl) acrylic ester as required.This epoxy radicals (methyl) acrylic ester, the compound that can preferably enumerate epoxy resin through having the epoxy radicals more than 2 in the molecule, obtain with the reaction of the monocarboxylic acid compound with ethylenically unsaturated group (preferred (methyl) acrylic acid).Epoxy resin as raw material can be enumerated: bisphenol type epoxy compound, for example bisphenol A type epoxy resin, bisphenol f type epoxy resin, bisphenol-s epoxy resin, 2, two (the 4-hydroxyphenyl)-1,1,1,3,3 of 2-, the epoxy compound of 3-HFC-236fa etc.; A Hydrogenated Bisphenol A type epoxy compound, for example bisphenol-A epoxy resin, A Hydrogenated Bisphenol A F type epoxy resin, A Hydrogenated Bisphenol A S type epoxy resin, hydrogenation 2, two (the 4-hydroxyphenyl)-1,1,1,3,3 of 2-, the epoxy compound of 3-HFC-236fa etc.; Halogenation bisphenol type epoxy compound, for example brominated bisphenol a type epoxy resin, brominated bisphenol F type epoxy resin etc.; The bisphenol-type epoxy resin of EO/PO modification; Ester ring type 2-glycidyl ether compound, for example cyclohexanedimethanodiglycidyl diglycidyl ether compound etc.; The aliphatic diglycidylether compound, for example 1,6-hexanediol diglycidyl ether, 1,4-butanediol diglycidyl ether, diethylene glycol diglycidyl ether etc.; Polysulfide type 2-glycidyl ether compound, for example polysulfide diglycidyl ether etc.; United phenol-type epoxy resin; Polyether-type epoxy resin etc.
The commercially available product of these epoxides for example can be enumerated: bisphenol A type epoxy resin, for example jER828, jER1001, jER1002, jER1003, jER1004(are Japan Epoxy Resins corporate system), EPOMIK
RTMR-140, EPOMIK
RTMR-301, EPOMIK
RTMR-304(is Mitsui Chemicals, Inc's system); DER-331, DER-332, DER-324(are Dow Chemical Co., Ltd. system); Epiclon 840, Epiclon 850(are big Japanese ink Co., Ltd. system); UVR-6410(Union Carbide Co., Ltd. system), YD-8125(Toto Kasei KK system) etc.; Bisphenol f type epoxy resin; UVR-6490(Union Carbide Co., Ltd. system for example); YDF-2001, YDF-2004, YDF-8170(are Toto Kasei KK's system), Epiclon 830, Epiclon 835(are big Japanese ink Co., Ltd. system) etc.; Bisphenol-A epoxy resin, for example HBPA-DGE(Maruzen Petrochemical Co., Ltd. system), リ カ レ ジ Application HBE-100(New Japan Chem Co., Ltd system) etc.; Brominated bisphenol a type epoxy resin, for example DER-513, DER-514, DER-542(are Dow Chemical Co., Ltd. system) etc.; The bisphenol A type epoxy resin of PO modification, for example EPOLIGHT 3002(Kyoeisha Chemical Co., Ltd. system) etc.; Deng alicyclic epoxy resin, Celloxide 2021(Daicel Co., Ltd. system for example), リ カ レ ジ Application DME-100(New Japan Chem Co., Ltd system) and, EX-216(Na ガ セ changes into Co., Ltd.'s system); Aliphatic diglycidylether compound, for example ED-503(rising sun electrification Co., Ltd. system), リ カ レ ジ Application W-100(New Japan Chem Co., Ltd system), EX-212, EX-214, EX-850(are Na ガ セ and change into Co., Ltd.'s system) etc.; Polysulfide type 2-glycidyl ether compound, for example FLEP-50, FLEP-60(are eastern レ チ オ コ one Le Co., Ltd. system) etc.; Xenol type epoxide, for example YX-4000(Japan Epoxy Resins Co., Ltd. system) etc.; Polyether-type epoxide, for example EPOLIGHT
RTM100E, EPOLIGHT
RTM200P(is Kyoeisha Chemical Co., Ltd.'s system) etc.
Subscript RTM representes registered trademark (below identical).
(D) Photoepolymerizationinitiater initiater that contains in the resin combination of the present invention can be enumerated: 1-hydroxycyclohexylphenylketone (Irgacure
RTM184; Ciba Specialty Chemicals Co., Ltd. system), 1-[4-(2-hydroxyl-oxethyl) phenyl]-2-hydroxy-2-methyl-1-propane-1-ketone (Irgacure
RTM2959; Ciba Specialty Chemicals Co., Ltd. system), 2-hydroxyl-1-{4-[4-(2-hydroxy-2-methyl-propiono) benzyl]-phenyl }-2-methyl isophthalic acid-propane-1-ketone (Irgacure
RTM127; Ciba Specialty Chemicals Co., Ltd. system), 2,2-dimethoxy-2-phenyl acetophenone (Irgacure
RTM651; Ciba Specialty Chemicals Co., Ltd. system), oligomeric [2-hydroxy-2-methyl-1-[4-(1-methyl ethylene) phenyl] acetone] (Esacure ONE; Lamberti Co., Ltd. system), 2-hydroxy-2-methyl-1-phenyl-propane-1-ketone (Darocure
RTM1173; Ciba Specialty Chemicals Co., Ltd. system), 2-methyl isophthalic acid-[4-(methyl mercapto) phenyl]-2-(N-morpholinyl) propane-1-ketone (Irgacure
RTM907; Ciba Specialty Chemicals Co., Ltd. system), 2-benzyl-2-dimethylamino-1-(4-(N-morpholinyl) phenyl)-butane-1-ketone, 2-clopenthixal ketone, 2; 4-dimethyl thioxanthones, 2; 4-diisopropyl thioxanthones, isopropyl thioxanthone, 2; 4,6-trimethylbenzoyl diphenyl phosphine oxide (Lucirin TPO; BASF Co., Ltd. system), two (2,4, the 6-trimethylbenzoyl) phenylphosphine oxide (Irgacure
RTM819; Ciba Specialty Chemicals Co., Ltd. system), two (2,6-dimethoxy benzoyl)-2,4,4-tri-methyl-amyl phosphine oxide etc.
These Photoepolymerizationinitiater initiaters can use a kind or mix multiple use with arbitrary proportion, also can cause the auxiliary agent combination with photopolymerization such as amine and use.
The content of (D) Photoepolymerizationinitiater initiater in the resin combination of the present invention uses 1 to 15 weight %, and preferred about 3 to about 10 weight %.
The photopolymerization such as amine that can use among the present invention cause auxiliary agent, for example can enumerate: diethanolamine, benzoic acid 2-dimethylaminoethyl, dimethylamino acetophenone, (dimethylamino)-ethyl benzoate, p-(dimethylamino)-benzoic acid isopentyl ester.
It is about 0 to about 5% that photopolymerization causes the content of auxiliary agent in resin combination of the present invention, more preferably from about 0 to about 3%.When combination used photopolymerization to cause auxiliary agent, preferred about 0.05 to about 5 weight %, and preferred about 0.1 to about 3 weight % especially.Usually need not make up and use photopolymerization to cause auxiliary agent.
In the resin combination of the present invention, can add phosphoric acid (methyl) acrylic ester as required.Phosphoric acid (methyl) acrylic ester can improve the tackiness of aluminium, silver or silver alloy and adhesive solidification thing, but might the corroding metal film, so its use amount is restricted.In addition, do not contain and can not throw into question.
In addition; Among the present invention; Except mentioned component, can make up the use adjuvant as required, for example silane coupling agent, levelling (leveling) agent, foam-breaking agent, polymerization inhibitor, light stabilizer (hindered amines etc.), anti-oxidant, antistatic agent, surface lubricant, filling agent etc.The example of such adjuvant for example can be enumerated: as KBM-502, KBM-503, KBM-5103, KBM-802, the KBM-803 of the SHIN-ETSU HANTOTAI of silane coupling agent chemistry (strain) corporate system; Z-6062, SH-6062, the SH-29PA of Toray Dow Corning (strain) corporate system; BYK-333, BYK-307, BYK-3500, BYK-3530, BYK-3570 as PVC Star Network ケ ミ one corporate system of levelling agent; As LA-82 of (strain) ア デ カ corporate system of anti-oxidant etc.
These adjuvants with respect to the total amount of resin combination of the present invention, can contain usually and have an appointment 0 to about 10%, preferred about 0 to about 5%.Usually do not contain yet and can not throw into question.
In addition, resin combination of the present invention, can be at normal temperature to 80 ℃ down with said each composition mixed dissolution after, filter as required and obtain.
The viscosity of resin combination of the present invention in the mensuration of Brookfield viscometer under 25 ℃, is 10 to 800mPas, and preferred 30 to 500mPas, and more preferably 30 to 400mPas, and further preferred 50 to 300mPas.
One example of resin combination of the present invention can be enumerated: whole with respect to resin combination; (A) composition be 5 to 90 weight %, (B) composition and/or (C) composition be that 5 to 90 weight %, (D) composition are 1 to 15 weight %, and (A) to the total amount of (D) be 100% ultraviolet-curing resin composition.
A preferred example of the composition of preferred resin combination of the present invention can be enumerated following resin combination.
(I)
A kind of resin combination; Wherein, With respect to the total amount of resin combination, (i) (A) composition is 5 to 90 weight %, (ii) (B) composition or (C) composition perhaps (B) and (C) the two is 5 to 90 weight %; And (A) total amount to (C) composition is 85 to 99 weight %, and (iii) (D) composition is 1 to 15 weight %.
(II)
One example of preferred resin combination is; A kind of resin combination; Wherein, (i) (A) composition is 10 to 40 weight %, (ii) (B) composition or (C) composition perhaps (B) and (C) the two is 50 to 90 weight %; And (A) total amount to (C) composition is 90 to 99 weight %, and (iii) (D) composition is 1 to 10 weight %.
(III)
Like above-mentioned (I) or (II) described resin combination, wherein, (A) composition is (methyl) acrylic ester with aliphatic chain by following formula (1) expression:
In the formula, R representes H or CH
3, n representes 10 to 25 integer.
(IV)
Like above-mentioned (III) described resin combination, wherein, (A) composition is (methyl) acrylic acid C10 to the C25 Arrcostab with side chain.
(V)
Like above-mentioned (IV) described resin combination; Wherein, (methyl) acrylic acid C10 to the C25 Arrcostab that has a side chain is for being selected from least a in the group that comprises isodecyl acrylate, (methyl) acrylic acid Permethyl 99A ester, (methyl) acrylic acid isooctadecane ester, (methyl) acrylic acid isohexadecane ester and the different docosane ester of (methyl) acrylic acid.
(VI)
Like above-mentioned (IV) described resin combination, wherein, (methyl) acrylic acid C10 to the C25 Arrcostab with side chain is for being selected from least a in the group that comprises isodecyl acrylate, (methyl) acrylic acid isooctadecane ester and (methyl) acrylic acid isohexadecane ester.
(VII)
Like above-mentioned (IV) described resin combination, wherein, (methyl) acrylic acid C10 to the C25 Arrcostab with side chain is (methyl) acrylic acid isooctadecane ester.
(VIII)
Like each described resin combination in above-mentioned (I) to (VII); Wherein, (B) composition comprises at least a (methyl) acrylate monomer in the group of trimethylolpropane two (methyl) acrylic ester of neopentyl glycol two (methyl) acrylic ester, tristane dimethanol two (methyl) acrylic ester and hydroxy pivalin aldehyde modification of (methyl) IBOA, epoxy pronane modification for being selected from.
(IX)
Like above-mentioned (VIII) described resin combination, wherein, (B) composition is any one in trimethylolpropane two (methyl) acrylic ester of (methyl) IBOA or hydroxy pivalin aldehyde modification.
(X)
Like each described resin combination in above-mentioned (I) to (IX), wherein, (C) carbamate (methyl) acrylic ester that obtains for the reaction through organic multiple isocyanate and hydroxyl (methyl) acrylate compounds of composition.
(XI)
Like above-mentioned (X) described resin combination, wherein, hydroxyl (methyl) acrylate compounds is substituted C2 to the C10 aliphatics of hydroxyl (methyl) acrylic ester.
(XII)
Like each described resin combination in above-mentioned (I) to (XI), wherein,, contain (B) composition of 50 to 90% with respect to the total amount of resin combination.
(XIII)
Like each described resin combination in above-mentioned (I) to (XII), wherein, with respect to (B) composition and (C) total amount of composition, (C) content of composition is 0 to 50%.
Resin combination of the present invention is suitable as the resin combination that the transparent intermediate layer of multiplayer optical disk is used.
During for DVD; The transparent resin middle layer forms in the following manner: (1) is through methods such as spin-coating method, silk screen print method, roller rubbing methods; With resin combination of the present invention be coated on range upon range of have on the substrate of first transparent resin substrate, first recording layer, the first semitransparent reflector rete and in the transparent resin pressing mold at least one after, fit and from transparent resin die-side irradiation ultraviolet radiation.Perhaps form in the following manner: after (2) are coated on resin combination of the present invention on the transparent resin pressing mold through said method; Carry out ultraviolet curing, again with ultraviolet curing resin and the range upon range of baseplate-laminating that first transparent resin substrate, first recording layer, the first semitransparent reflector rete are arranged arbitrarily.(1) formation method is considered from the viewpoint that can omit production process, is expected to reduce production costs, and is therefore preferred.In addition, during for Blu-ray Disc, also can form the transparent resin middle layer with the method identical with DVD.Generally speaking, the resin substrate of first transparent resin substrate of the 0.6mm of DVD or HD-DVD, the 1.1mm of Blu-ray Disc uses polycarbonate resin.
The transparent resin pressing mold for example can be enumerated: acrylic resin, methacrylic resin, polycarbonate resin, polyolefin resin (particularly noncrystalline polyolefin), polyester resin, polystyrene resin, epoxy resin etc.Wherein, viewpoints such as the fissility after solidifying from the 2P agent, agent of low hygroscopicity, shape stability consider that preferred noncrystalline polyolefin is considered from the viewpoint of material cost, the optimization polycarbonate resin.2P curable resin composition of the present invention can use any one transparent resin pressing mold.
Ultraviolet-curing resin composition of the present invention, the irradiation through active energy ray obtains solidfied material.This active energy ray for example can be enumerated: ultraviolet near ultraviolet light.The light source of this light for example can be enumerated: low pressure, high pressure, extra-high-pressure mercury vapour lamp, metal halide lamp, (pulse) xenon lamp, electrodeless lamp, ultraviolet LED etc.Said solidfied material is also contained among the present invention.
Be formed at the recording layer on the transparent resin middle layer that constitutes by said solidfied material, can use any one in organic pigment and the phase-change material.For example, organic pigment can be enumerated: containing metal azo class, polymethine (Port リ メ チ Application) class, phthalocyanines; Phase-change material can be enumerated: in Sb and Te, add more than among In, Ag, Au, Bi, Se, Al, P, Ge, Si, C, V, W, Ta, Zn, Ti, Ce, Tb, Sn, the Pb any one and the material that obtains.
In addition, resin combination of the present invention can be used for being fitted with any one of CD and Blu-ray Disc of the structure of polycarbonate system substrate.
Coating process for example can be enumerated: spin-coating method, 2P method, roller rubbing method, silk screen print method etc.
In addition, in the follow-on high density compact disc, read and/or write the blue laser that uses about 400nm, the solidfied material of therefore preferred thickness 90 to 100 μ m, the transmissivity of the 405nm among the preferred 100 μ m is more than 80%, more preferably more than 90%.
About transmissivity, can make the film of 100 μ m, and use spectrophotometer (U-3310, Hitachi High Technologies Co., Ltd. system), measure this film and try to achieve in the value of the absorbance of 405nm.
(embodiment)
Below use embodiment to specify the present invention.
In addition, the viscosity number that table 1 is put down in writing is 25 ℃ of values of being measured down with Brookfield viscometer.In addition, the transmittance values that table 1 is put down in writing is the cured film of making thickness 100 μ m, and the value of using spectrophotometer (marque: U-3310, Hitachi High Technologies Co., Ltd. system) to be measured.
(embodiment and Test Example)
Table 1 illustrates the evaluation result of constituent material, use amount and the record project of the resin combination of embodiment 1-6 and comparative example 1-4." part " expression weight portion in the record content.
Table 1
Table 1. resin is formed and evaluation result
Each composition that abbreviation in the table 1 is represented is described below.
ISA: acrylic acid isooctadecane ester, Xin Zhong village chemical industrial company system
ICA: acrylic acid isohexadecane ester, Kyoeisha Chemical Co., Ltd.'s system
IDA: isodecyl acrylate, Kyoeisha Chemical Co., Ltd.'s system
SA: acrylic acid octadecane ester, Japan Oil Co's system
CA: acrylic acid hexadecane ester, Japan Oil Co's system
IBA: IBOA, Osaka Organic Chemical Industry Co., Ltd.'s system
R-604: the trimethylolpropane diacrylate of hydroxy pivalin aldehyde modification, Nippon Kayaku K. K's system
R-684: tristane dimethanol diacrylate, Nippon Kayaku K. K's system
NPG-2P: the neopentylglycol diacrylate of epoxy pronane modification, Di-ichi Kogyo Seiyaku Co., Ltd.'s system
FA-512A: acrylic acid dicyclopentadiene base oxygen base ethyl ester, Hitachi changes into Co., Ltd.'s system
THE-330: the trimethylolpropane acrylates of hydroxy pivalin aldehyde modification, Nippon Kayaku K. K's system
RP-1040: the tetraacrylate of pentaerythrite oxirane modification, Nippon Kayaku K. K's system
DPHA: dipentaerythritol acrylate, Nippon Kayaku K. K's system
UX-5000: six sense urethane acrylates, Nippon Kayaku K. K's system
Irgacure
RTMThe 184:1-hydroxycyclohexylphenylketone, Ciba Specialty Chemicals Co., Ltd. system
C1: IPDI and hydroxy-ethyl acrylate are reacted and the urethane acrylate that obtains with mol ratio
(estimating making) with sample
Use resulting ultraviolet-curing resin composition, make to estimate through following 1 to 3 method and use sample disc.
Be formed with azo class uvea as recording layer, reflective coating, as the ZnSSiO of dielectric layer
2Go up the transparent resin of processing with the mode that bubble is got in the thick polycarbonate system substrate (first substrate) of diameter 120mm/0.6mm of layer week and upload and put polycarbonate and neutralize mould, under 2000rpm, carry out 4 seconds rotary coating and applying.
2. from polycarbonate system die-side, with 400mJ/cm
2Irradiation high-pressure mercury-vapor lamp (80W/cm) solidifies second ultraviolet-curing resin composition.
3. use CD stripping off device (Origin Electric Co., Ltd system), this polycarbonate is neutralized mould (transparent resin pressing mold) peel off, process to estimate and use sample disc.
(a) fissility test
Through using CD stripping off device (Origin Electric Co., Ltd system); And use tester (FGC-5B; Nidec-Shimpo (strain) corporate system) measuring above-mentioned evaluation neutralizes peel strength that mould peel off from polycarbonate with sample disc (diameter 120mm, radius 60mm) when processing and carries out.
Peeling off the judgement of formedness carries out with following benchmark.
Zero ... below the peel strength 1.5kgf
* ... more than the peel strength 1.5kgf
(b) camber test
The warpage numerical value of resin bed, through be formed with azo class uvea as recording layer, reflective coating, as the ZnSSiO of dielectric layer
2Go up in week in the thick polycarbonate system substrate (first substrate) of diameter 120mm/0.6mm of layer and use the rotary coating machine to be coated with each resin combination, and use is measured as the MT-146 (Dr.schenk corporate system) of the mechanical property device of CD so that thickness becomes the mode of 10 ± 3 μ m after curing.Because warp value is along with past periphery is big more, so being that the warp value (degree) of 56mm is estimated near most peripheral apart from cd centre.
The initial stage warpage is calculated through following (mathematical expression 1).
Disc tilt (degree) before the coating of disc tilt (the degree)-ultraviolet-curing resin composition after the coating of warpage variable quantity (the degree)=ultraviolet-curing resin composition when (mathematical expression 1) solidifies is solidified, warpage unit representes to spend.
Zero ... the warpage variable quantity during curing is less than ± 0.1 degree
* ... the warpage variable quantity during curing is more than ± 0.1 degree
(c) endurancing
Endurancing; The sample disc that in the operation of camber test, process is in 80 ℃, 85% high temperature wet condition held 96 hours how; After at room temperature preserving 24 hours then; How wet the warpage angle of (before being positioned under the high temperature condition) before the warpage angle that obtains and the test compared, calculate the variable quantity of this warpage angle.Because warp value is along with past periphery is big more, so being that the warp value of 56mm is estimated near most peripheral apart from cd centre.In addition, measure the MT-146 (Dr.schenk corporate system) that uses as the mechanical property device of CD.
The variable quantity of warpage after the endurancing and initial stage warpage (degree) calculates through following (mathematical expression 2).
Disc tilt (degree) before disc tilt (degree) after warpage variable quantity=endurancing after (mathematical expression 2) endurancing-test.
Zero ... the warpage variable quantity after the endurancing is less than ± 0.5 degree
* ... the warpage variable quantity after the endurancing is more than ± 0.5 degree
From table 1, can learn; Embodiment 1 to 6 as ultraviolet-curing resin composition of the present invention and solidfied material thereof; Compare with the comparative example 1 to 4 that does not use (methyl) acrylic ester with aliphatic chain; How wet even be placed on back (after the endurancing) under the high temperature condition, the warpage variable quantity is also less.In addition, in comparative example that uses multiple polyfunctional acrylic ester monomer 2 and comparative example 3, peel strength is strong, so fissility worsens; In the comparative example 4, though fissility is good, as stated; Warpage variable quantity after the endurancing is big, and is described below, and the warpage during curing is also big.
That is, during warpage variable quantity when observe solidifying, ultraviolet-curing resin composition of the present invention is the minimum value of 0.08 to 0.09 degree.Comparative example 1, poor though the warpage variable quantity when solidifying be on an equal basis from the fissility that resin moulding-die is peeled off, and the warpage variable quantity after the endurancing is also big.In comparative example 2, comparative example 3 and the comparative example 4, the warpage variable quantity during curing is the higher value of 0.15 to 0.36 degree.
In addition, when observing the viscosity of ultraviolet-curing resin composition of the present invention, viscosity is in 30 to 500mPas the scope, for being suitable for forming the viscosity of resin bed.In addition, the light transmission of solidfied material surpasses 90%, considers also good from the viewpoint of optical transmission degree.
From above content, can learn; Ultraviolet-curing resin composition of the present invention; Be suitable for and be formed directly on the reflection horizon or dielectric layer on the optic disc base board through the transparent resin layer with relief pattern (middle resin layer) that pressing mold, particularly polycarbonate pressing mold are processed, and be for recording layer or the extremely useful resin combination of even formation of reflective coating on this relief pattern.
Industrial applicability
Ultraviolet-curing resin composition of the present invention and solidfied material thereof, useful as the 2P agent, this 2P agent is that the fissility of peeling off from resin moulding-die is good, and it is little when solidifying and with multiplayer optical disk, to be placed on the warpage variable quantity of high temperature after how under the wet condition.In addition, can provide a kind of can omit adhesive layer and form the ultraviolet curing resin of middle resin layer with single component.
Claims (12)
1. a multiplayer optical disk is used ultraviolet-curing resin composition; It is characterized in that, contain: (methyl) acrylic ester, (B) (methyl) acrylate monomer and/or (C) carbamate (methyl) acrylic ester and (D) Photoepolymerizationinitiater initiater that (A) have aliphatic chain.
2. multiplayer optical disk as claimed in claim 1 is used ultraviolet-curing resin composition; Wherein, (methyl) acrylic ester that (A) has an aliphatic chain comprise for being selected from the group of (methyl) acrylic acid dodecane ester, (methyl) acrylic acid octadecane ester, (methyl) acrylic acid hexadecane ester, (methyl) acrylic acid docosane ester, (methyl) acrylic acid Permethyl 99A ester, (methyl) acrylic acid isooctadecane ester, (methyl) acrylic acid isohexadecane ester and the different docosane ester of (methyl) acrylic acid more than a kind or 2 kinds.
3. multiplayer optical disk as claimed in claim 1 is used ultraviolet-curing resin composition; Wherein, (B) (methyl) acrylate monomer comprise for being selected from the group of trimethylolpropane two (methyl) acrylic ester of neopentyl glycol two (methyl) acrylic ester, tristane dimethanol two (methyl) acrylic ester and hydroxy pivalin aldehyde modification of (methyl) IBOA, epoxy pronane modification more than a kind or 2 kinds.
4. use ultraviolet-curing resin composition like each described multiplayer optical disk in the claim 1 to 3; Wherein, whole with respect to resin combination, (A) composition is 5 to 90 weight %; (B) composition and/or (C) composition be 5 to 90 weight %, (D) composition is 1 to 15 weight %.
5. CD, it has the solidfied material that the described resin combination irradiation ultraviolet radiation of claim 1 is obtained.
6. ultraviolet-curing resin composition, it contains:
(A) (methyl) acrylic ester of representing by following formula (1) with aliphatic chain:
In the formula, R representes H or CH
3, n representes 10 to 25 integer; And
(B) be selected from least a (methyl) acrylate monomer in the group of trimethylolpropane two (methyl) acrylic ester of neopentyl glycol two (methyl) acrylic ester, tristane dimethanol two (methyl) acrylic ester and the hydroxy pivalin aldehyde modification that comprise (methyl) IBOA, epoxy pronane modification; Perhaps carbamate (methyl) acrylic ester that obtains of (C) reaction through organic multiple isocyanate and hydroxyl (methyl) acrylate compounds; And
(D) Photoepolymerizationinitiater initiater, and,
With respect to the total amount of resin combination,
(i) (A) composition is 5 to 90 weight %,
(ii) (B) composition or (C) composition perhaps (B) and (C) the two is 5 to 90 weight %, (A) total amount to (C) composition is 85 to 99 weight %,
(iii) (D) composition is 1 to 15 weight %.
7. ultraviolet-curing resin composition as claimed in claim 6, wherein, the aliphatic chain with (methyl) acrylic ester of aliphatic chain is the aliphatic chain with side chain.
8. ultraviolet-curing resin composition as claimed in claim 7; Wherein, (methyl) acrylic ester that has an aliphatic chain is for being selected from least a in the group that comprises isodecyl acrylate, (methyl) acrylic acid Permethyl 99A ester, (methyl) acrylic acid isooctadecane ester, (methyl) acrylic acid isohexadecane ester and the different docosane ester of (methyl) acrylic acid.
9. ultraviolet-curing resin composition as claimed in claim 6; Wherein, Organic multiple isocyanate comprises IPDI, 1 for being selected from; Hexamethylene-diisocyanate, toluene diisocyanate, XDI and diphenyl methane-4,4 '-at least a diisocyanate or tetrahydrochysene dicyclopentadiene based isocyanate in the group of diisocyanate.
10. ultraviolet-curing resin composition as claimed in claim 6, wherein, hydroxyl (methyl) acrylate compounds is substituted C2 to the C10 aliphatics of hydroxyl (methyl) acrylic ester.
11. the purposes of the described ultraviolet-curing resin composition of claim 6, it is used for the middle resin layer of multiplayer optical disk.
12. a multiplayer optical disk, it has the solidfied material layer of the described ultraviolet-curing resin composition of claim 6.
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| JP2009-167454 | 2009-07-16 | ||
| JP2009167454A JP5448152B2 (en) | 2009-07-16 | 2009-07-16 | Ultraviolet curable resin composition for optical disc and cured product thereof |
| PCT/JP2010/004591 WO2011007571A1 (en) | 2009-07-16 | 2010-07-15 | Ultraviolet-curable resin composition for use in optical disks and cured products thereof |
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| CN (1) | CN102473432A (en) |
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|---|---|---|---|---|
| JPH05140254A (en) * | 1991-11-19 | 1993-06-08 | Dainippon Ink & Chem Inc | Ultraviolet-curing resin composition |
| JP2007002144A (en) * | 2005-06-27 | 2007-01-11 | Nippon Kayaku Co Ltd | Ultraviolet-curing type resin composition and its cured product |
| CN101171278A (en) * | 2005-05-12 | 2008-04-30 | 日本化药株式会社 | Photosensitive resin compositions, cured articles of the compositions, and films containing the compositions |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006161030A (en) * | 2004-11-09 | 2006-06-22 | Mitsubishi Chemicals Corp | Radiation curable composition, its cured product and laminate |
| JP2006241234A (en) * | 2005-03-01 | 2006-09-14 | Nippon Synthetic Chem Ind Co Ltd:The | Optical recording medium and coating agent therefor |
| JP2007234189A (en) * | 2006-03-03 | 2007-09-13 | Toyo Ink Mfg Co Ltd | Active energy ray curing resin composition for optical disk and optical disk obtained by using the same |
| CN101589433A (en) * | 2007-03-23 | 2009-11-25 | Dic株式会社 | Ultraviolet-curable composition for optical disk intermediate layer and optical disk |
-
2009
- 2009-07-16 JP JP2009167454A patent/JP5448152B2/en not_active Expired - Fee Related
-
2010
- 2010-07-15 WO PCT/JP2010/004591 patent/WO2011007571A1/en active Application Filing
- 2010-07-15 SG SG2011085420A patent/SG176165A1/en unknown
- 2010-07-15 TW TW099123240A patent/TW201111432A/en unknown
- 2010-07-15 CN CN2010800317632A patent/CN102473432A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05140254A (en) * | 1991-11-19 | 1993-06-08 | Dainippon Ink & Chem Inc | Ultraviolet-curing resin composition |
| CN101171278A (en) * | 2005-05-12 | 2008-04-30 | 日本化药株式会社 | Photosensitive resin compositions, cured articles of the compositions, and films containing the compositions |
| JP2007002144A (en) * | 2005-06-27 | 2007-01-11 | Nippon Kayaku Co Ltd | Ultraviolet-curing type resin composition and its cured product |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2011007571A1 (en) | 2011-01-20 |
| JP5448152B2 (en) | 2014-03-19 |
| JP2011023072A (en) | 2011-02-03 |
| SG176165A1 (en) | 2011-12-29 |
| TW201111432A (en) | 2011-04-01 |
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Application publication date: 20120523 |