TWI401532B - A photographic resin composition for volume phase type image recording, and an optical information recording medium using the composition - Google Patents
A photographic resin composition for volume phase type image recording, and an optical information recording medium using the composition Download PDFInfo
- Publication number
- TWI401532B TWI401532B TW095107268A TW95107268A TWI401532B TW I401532 B TWI401532 B TW I401532B TW 095107268 A TW095107268 A TW 095107268A TW 95107268 A TW95107268 A TW 95107268A TW I401532 B TWI401532 B TW I401532B
- Authority
- TW
- Taiwan
- Prior art keywords
- resin composition
- volume phase
- recording
- phase type
- photosensitive resin
- Prior art date
Links
- 239000011342 resin composition Substances 0.000 title claims abstract description 39
- 239000000203 mixture Substances 0.000 title description 14
- 230000003287 optical effect Effects 0.000 title description 7
- 229920001577 copolymer Polymers 0.000 claims abstract description 64
- -1 divinyl aromatic compound Chemical class 0.000 claims abstract description 41
- 150000001875 compounds Chemical class 0.000 claims abstract description 35
- 239000004014 plasticizer Substances 0.000 claims abstract description 15
- 150000001491 aromatic compounds Chemical class 0.000 claims abstract description 14
- 229920005596 polymer binder Polymers 0.000 claims abstract description 14
- 239000002491 polymer binding agent Substances 0.000 claims abstract description 14
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims abstract description 13
- 238000000034 method Methods 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 239000000463 material Substances 0.000 abstract description 33
- 239000003999 initiator Substances 0.000 abstract description 17
- 230000035945 sensitivity Effects 0.000 abstract description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 28
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 18
- 239000000178 monomer Substances 0.000 description 18
- 238000006116 polymerization reaction Methods 0.000 description 16
- 239000002904 solvent Substances 0.000 description 11
- 229920002554 vinyl polymer Polymers 0.000 description 11
- 239000000975 dye Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000004593 Epoxy Substances 0.000 description 9
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 9
- 238000013500 data storage Methods 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 9
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- 239000003960 organic solvent Substances 0.000 description 7
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- 230000015572 biosynthetic process Effects 0.000 description 6
- 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 6
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 6
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethylcyclohexane Chemical compound CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 6
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- MPMBRWOOISTHJV-UHFFFAOYSA-N but-1-enylbenzene Chemical compound CCC=CC1=CC=CC=C1 MPMBRWOOISTHJV-UHFFFAOYSA-N 0.000 description 5
- 238000010538 cationic polymerization reaction Methods 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 5
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- 239000000049 pigment Substances 0.000 description 5
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- 235000007586 terpenes Nutrition 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
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- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- 206010034960 Photophobia Diseases 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- QCCDYNYSHILRDG-UHFFFAOYSA-K cerium(3+);trifluoride Chemical compound [F-].[F-].[F-].[Ce+3] QCCDYNYSHILRDG-UHFFFAOYSA-K 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 239000003822 epoxy resin Substances 0.000 description 4
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 4
- 208000013469 light sensitivity Diseases 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229920000647 polyepoxide Polymers 0.000 description 4
- 230000037048 polymerization activity Effects 0.000 description 4
- 239000003505 polymerization initiator Substances 0.000 description 4
- 238000010526 radical polymerization reaction Methods 0.000 description 4
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 4
- QPBYLOWPSRZOFX-UHFFFAOYSA-J tin(iv) iodide Chemical compound I[Sn](I)(I)I QPBYLOWPSRZOFX-UHFFFAOYSA-J 0.000 description 4
- IYSVFZBXZVPIFA-UHFFFAOYSA-N 1-ethenyl-4-(4-ethenylphenyl)benzene Chemical group C1=CC(C=C)=CC=C1C1=CC=C(C=C)C=C1 IYSVFZBXZVPIFA-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
- 239000012965 benzophenone Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- VYLVYHXQOHJDJL-UHFFFAOYSA-K cerium trichloride Chemical compound Cl[Ce](Cl)Cl VYLVYHXQOHJDJL-UHFFFAOYSA-K 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229910001873 dinitrogen Inorganic materials 0.000 description 3
- 230000007613 environmental effect Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 235000013847 iso-butane Nutrition 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 229910001507 metal halide Inorganic materials 0.000 description 3
- 150000005309 metal halides Chemical class 0.000 description 3
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 238000012719 thermal polymerization Methods 0.000 description 3
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 3
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 2
- CRRUGYDDEMGVDY-UHFFFAOYSA-N 1-bromoethylbenzene Chemical compound CC(Br)C1=CC=CC=C1 CRRUGYDDEMGVDY-UHFFFAOYSA-N 0.000 description 2
- XIRPMPKSZHNMST-UHFFFAOYSA-N 1-ethenyl-2-phenylbenzene Chemical group C=CC1=CC=CC=C1C1=CC=CC=C1 XIRPMPKSZHNMST-UHFFFAOYSA-N 0.000 description 2
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 2
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- KPJKMUJJFXZGAX-UHFFFAOYSA-N 2-chloropropan-2-ylbenzene Chemical compound CC(C)(Cl)C1=CC=CC=C1 KPJKMUJJFXZGAX-UHFFFAOYSA-N 0.000 description 2
- 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 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 2
- FOXXZZGDIAQPQI-XKNYDFJKSA-N Asp-Pro-Ser-Ser Chemical compound OC(=O)C[C@H](N)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CO)C(=O)N[C@@H](CO)C(O)=O FOXXZZGDIAQPQI-XKNYDFJKSA-N 0.000 description 2
- 229930185605 Bisphenol Natural products 0.000 description 2
- 229910008069 Cerium(III) iodide Inorganic materials 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
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- 239000002841 Lewis acid Substances 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
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- 239000004793 Polystyrene Substances 0.000 description 2
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- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
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- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 2
- 229910021623 Tin(IV) bromide Inorganic materials 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- RPJGYLSSECYURW-UHFFFAOYSA-K antimony(3+);tribromide Chemical compound Br[Sb](Br)Br RPJGYLSSECYURW-UHFFFAOYSA-K 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 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
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
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- 125000002091 cationic group Chemical group 0.000 description 2
- ZEDZJUDTPVFRNB-UHFFFAOYSA-K cerium(3+);triiodide Chemical compound I[Ce](I)I ZEDZJUDTPVFRNB-UHFFFAOYSA-K 0.000 description 2
- ISYHKYCCIRAQTC-UHFFFAOYSA-J cerium(4+) tetrabromide Chemical compound [Br-].[Br-].[Br-].[Br-].[Ce+4] ISYHKYCCIRAQTC-UHFFFAOYSA-J 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical group [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 2
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- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
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- JBVOSZYUSFDYIN-UHFFFAOYSA-N dimethyl cyclopropane-1,2-dicarboxylate Chemical compound COC(=O)C1CC1C(=O)OC JBVOSZYUSFDYIN-UHFFFAOYSA-N 0.000 description 2
- ALOUNLDAKADEEB-UHFFFAOYSA-N dimethyl sebacate Chemical compound COC(=O)CCCCCCCCC(=O)OC ALOUNLDAKADEEB-UHFFFAOYSA-N 0.000 description 2
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- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
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- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 2
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- JKNHZOAONLKYQL-UHFFFAOYSA-K tribromoindigane Chemical compound Br[In](Br)Br JKNHZOAONLKYQL-UHFFFAOYSA-K 0.000 description 2
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- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
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- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
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- 125000000524 functional group Chemical group 0.000 description 1
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- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
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- XNGIFLGASWRNHJ-UHFFFAOYSA-N o-dicarboxybenzene Natural products OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
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- MUUZIDFBKZNXQS-UHFFFAOYSA-N oxido-phenyl-[(2,4,6-trimethylphenyl)methylidene]phosphanium Chemical compound CC1=C(C=P(C2=CC=CC=C2)=O)C(=CC(=C1)C)C MUUZIDFBKZNXQS-UHFFFAOYSA-N 0.000 description 1
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- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 1
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- 238000005191 phase separation Methods 0.000 description 1
- HWPQNZSKIFFJEF-UHFFFAOYSA-N phosphoric acid;trimethyl phosphate Chemical class OP(O)(O)=O.COP(=O)(OC)OC HWPQNZSKIFFJEF-UHFFFAOYSA-N 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
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- 238000001556 precipitation Methods 0.000 description 1
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- 230000001681 protective effect Effects 0.000 description 1
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- 239000000376 reactant Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
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- 239000001022 rhodamine dye Substances 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
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- 239000003381 stabilizer Substances 0.000 description 1
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- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 1
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- 239000010936 titanium Substances 0.000 description 1
- UBZYKBZMAMTNKW-UHFFFAOYSA-J titanium tetrabromide Chemical compound Br[Ti](Br)(Br)Br UBZYKBZMAMTNKW-UHFFFAOYSA-J 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- YSCVYRUCAPMZFG-UHFFFAOYSA-K trichlorotin Chemical compound Cl[Sn](Cl)Cl YSCVYRUCAPMZFG-UHFFFAOYSA-K 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- JNLSTWIBJFIVHZ-UHFFFAOYSA-K trifluoroindigane Chemical compound F[In](F)F JNLSTWIBJFIVHZ-UHFFFAOYSA-K 0.000 description 1
- YVXBULZEXSZKHU-UHFFFAOYSA-K trifluoroplatinum Chemical compound [Pt](F)(F)F YVXBULZEXSZKHU-UHFFFAOYSA-K 0.000 description 1
- RMUKCGUDVKEQPL-UHFFFAOYSA-K triiodoindigane Chemical compound I[In](I)I RMUKCGUDVKEQPL-UHFFFAOYSA-K 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- GRPURDFRFHUDSP-UHFFFAOYSA-N tris(prop-2-enyl) benzene-1,2,4-tricarboxylate Chemical compound C=CCOC(=O)C1=CC=C(C(=O)OCC=C)C(C(=O)OCC=C)=C1 GRPURDFRFHUDSP-UHFFFAOYSA-N 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
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Classifications
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
- G03F7/0388—Macromolecular compounds which are rendered insoluble or differentially wettable with ethylenic or acetylenic bands in the side chains of the photopolymer
-
- 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
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
- G03F7/001—Phase modulating patterns, e.g. refractive index patterns
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
- G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03H—HOLOGRAPHIC PROCESSES OR APPARATUS
- G03H1/00—Holographic processes or apparatus using light, infrared or ultraviolet waves for obtaining holograms or for obtaining an image from them; Details peculiar thereto
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Description
本發明係有關，適合作為可藉由活性能量線(可見光或紫外線、電子線等)快速進行光硬化，能形成衍射效率、解像力等全像特性良好，且透明性、耐熱性等優異之厚膜的體積相位型全像之材料的體積相位型全像記錄用感光性樹脂組成物，及使用其之光資訊記錄媒體者。
以往，全像主要使用於立體畫像顯示領域．安全領域。其全像材料，最早以使用必要銀鹽感光材料或重鉻酸明膠等顯像之濕式型材料為主；其後，成為以不必要顯像處理之記錄後的耐環境性．耐光性優越之乾式光聚合型全像記錄材料為主流。光聚合型全像記錄材料之記錄機構，與銀鹽感光材料或重鉻酸明膠等不同，一般而言有如下之考量。就是說，由同調性(可干擾性)優越之光的干擾所成之干擾條紋照射於記錄材料時，分別聚合性不同的物質在光之明亮部(光強度強之區域)、陰暗部(光強度弱之區域)，擴散移動，進行光聚合同時形成折射率調製結構，而全像記錄。光聚合型全像記錄材料之聚合形態，有(1)自由基聚合型、(2)陽離子聚合型、(3)自由基/陽離子聚合併用型。光自由基聚合型之材料最為普遍，雖感度高，有起因於共聚合形態之收縮，大至數%的缺點。目前，光聚合型全像記錄材料中，唯一市售之感光性樹脂組成物，只有美國杜邦公司之歐姆尼鐵庫斯。
近年來，在面對優比奇達斯資訊化社會之實現的競爭中，將光聚合型全像記錄材料使用於全像．數據存儲之研究，再度活躍於世界中，有各種各樣之光聚合型全像記錄材料的提案。此係，在1990年代中葉由以美國為首之國家計劃HDSS(Holographic Data Storage System：1995－1999)、PRISM(Photorefractive Information Storage Materials：1994－1998)所推進之計劃中，大有助於電射光源或空間光調製器等技術之飛躍進步。以往之CD、DVD等對光碟的記錄，係以透鏡將雷射光聚光，以一個個比特記錄之方式使數據存儲於記錄材料面。以此聚光點之大小決定數據記憶容量，有其理論界限；進而，為增大記錄容量，期望有新的技術之開發。其候補之一有近年頗受注目的全像照相術。
全像．數據存儲，並非如CD、DVD之面內記錄，可體積記錄；處理數據亦可使用頁面數據之故，能記錄以往之CD、DVD所不能比的大量數據。目前，面對可記錄1TB(鐵拉比特)之WORM(Write Once Read Many：補記)型全像光碟之實用化，各研究機構均熱烈進行材料開發及記錄技術之開發。全像．數據存儲用材料之基本設計的考量，與上述之立體畫像記錄或安全用途的光聚合型全像記錄材料相同。但是，使用於全像．數據存儲用途之情況，相對於使用光源的感度、或相對硬化收縮率之材料的要求極為嚴格。此全像．數據存儲用感光性樹脂組成物的代表例有，與美國波拉洛依多公司同流之美國阿利利斯公司者、及與美國魯現多．技術公司同流之美國因費茲公司者。
首先，美國阿普利利斯公司，例如在專利文獻1、2中之記載，有使用環氧乙烷，具有氧雜環丁烷環之CROP(陽離子開環聚合)單體，藉由予以預光照射，可抑制聚合收縮之材料的揭示。不過，陽離子聚合，雖係氧妨礙極少之自由基聚合，但在長波長區域之感度有稍微劣化的問題。另一方面，美國因費茲公司，例如在專利文獻3、4或5中之記載，有藉由併用環己烯氧化物與膨脹劑(二苯呋喃羧酸鹽)，可使聚合收縮率降低至極少之1%以下的材料之揭示。不過，於此，採用陽離子開環聚合性單體，將其於記錄前或後，全面曝光，雖可抑制硬化收縮，但相對於感度提升卻無任何提案。面對全像．數據存儲之實用化，期望更提升光感度與降低硬化收縮率，且提高耐熱性。
專利文獻1：美國專利第5,759,721號說明書專利文獻2：美國專利第6,784,300號說明書專利文獻3：美國專利第3,993,485號說明書專利文獻4：美國專利第6,124,076號說明書專利文獻5：特開2000－086914號公報專利文獻6：特開平5－94014號公報專利文獻7：特開平9－106242號公報專利文獻8：特開2004－123873號公報
專利文獻6、7中有，配合自由基聚合性之乙烯系單體、光聚合引發劑與環氧樹脂之全像用的感光性樹脂組成物之記載。此組成物係，在以雷射使全像曝光時，自干擾條紋之明亮部份優先聚合自由基聚合性的乙烯系單體，利用乙烯系單體在明亮部份的移動之現象形成全像。還有，環氧樹脂係於其後硬化。專利文獻8中，雖有具有二乙烯基芳香族化合物之結構單位與單乙烯基芳香族化合物之結構單位的可溶性芳香族共聚物之記載，但就全像用途並無任何指教。
可記錄體積相位型全像之感光性樹脂組成物，目前為止雖有數量甚多之就材料系的檢討之揭示，但並無可同時滿足光感度與硬化收縮率雙方之感光性樹脂組成物。在使用作為全像．數據存儲用之體積相位型全像記錄用樹脂組成物時，關於光感度與低硬化收縮率之兩者，尤其要求高標準。
本發明鑑於上述各項問題，提供一種體積相位型全像所要求之衍射效率、解像力、透明性、耐熱性等良好，且光感度極優越之體積相位型全像記錄用樹脂組成物，及由該組成物而得之光資訊記錄媒體。當然，藉由本發明而得之全像，可使用於全像．數據存儲用以外之用途，例如衍射晶格、干擾濾光片、透鏡、仰視顯示器等使用全像可發揮其有效性之用途。
本發明的工作同仁針對上述課題，經深入探討不斷研究之結果發現，組成物中配合可溶性多官能乙烯基芳香族共聚物、及可與其共聚合之光自由基聚合性化合物，可更提高感光性，同時能更抑制硬化後之收縮，完成本發明。
本發明係一種體積相位型全像記錄用感光樹脂組成物，其特徵為具有二乙烯基芳香族化合物之結構單位與單乙烯基芳香族化合物之結構單位，含有：含10莫耳%以上之下述式(a1)所示之結構單位的可溶性芳香族共聚物(A)、可與可溶性芳香族共聚物(A)共聚合之光自由基聚合性化合物(B)、及光聚合引發劑(C)、與高分子結合劑(D)、及/或增塑劑(E)，所成之感光性樹脂組成物；其中含有5~60重量%之可溶性芳香族共聚物(A)。
又，本發明係，由該感光性樹脂組成物所成之記錄層，為形成於一個支撑體上或兩個支撑體之間所成的體積相位型全像記錄用光資訊記錄媒體。進而，本發明係在該光資訊記錄媒體上，進行記錄由同調性優越之能量線所形成的干擾條紋而得之體積相位型全像。又，本發明係一種體積相位型全像之製造方法，其特徵為在該記錄媒體上，予以曝光記錄由同調性優越之能量線所形成的干擾條紋。
本發明之感光性樹脂組成物，係為記錄使由同調性優越的光之干擾所成的干擾條紋作為折射率相異之條紋，所使用的體積相位型全像記錄用樹脂組成物。含有可溶性芳香族共聚物(A)、光自由基聚合性化合物(B)及光聚合引發劑(C)為必要成份。進而，含有高分子結合劑(D)或增塑劑(E)或兩者為必要成份。
首先，就可溶性芳香族共聚物(A)予以說明。
可溶性芳香族共聚物(A)，係將二乙烯基芳香族化合物與單乙烯基芳香族化合物共聚合而得，具有10莫耳%以上之上述式(a1)所示的側鏈上含有反應性乙烯基之結構單位。式(a1)所示之結構單位，係自二乙烯基芳香族化合物之單體。1分子中平均具有3以上之式(a1)所示的結構單位為佳。又，可溶性芳香族共聚物(A)，係專利文獻8等記載之眾所周知的化合物，藉由其記載之方法可製得。
二乙烯基芳香族化合物，可使用例如間－二乙烯基苯、對－二乙烯基苯、1,2－二異丙烯基苯、1,3－二異丙烯基苯、1,4－二異丙烯基苯、1,3－二乙烯基萘、1,8－二乙烯基萘、1,4－二乙烯基萘、1,5－二乙烯基萘、2,3－二乙烯基萘、2,7－二乙烯基萘、2,6－二乙烯基萘、4,4'－二乙烯基聯苯、4,3'－二乙烯基聯苯、4,2'－二乙烯基聯苯、3,2'－二乙烯基聯苯、3,3'－二乙烯基聯苯、2,2'－二乙烯基聯苯、2,4－二乙烯基聯苯、1,2－二乙烯基－3,4－二甲基苯、1,3－二乙烯基－4,5,8－三丁基萘、2,2'－二乙烯基－4－乙基－4'－丙基聯苯等。此等沒有任何限制。此等可單獨或兩種以上組合使用。
二乙烯基芳香族化合物之較佳具體例，從成本及所得聚合物之耐熱性的觀點而言，有二乙烯基苯(間－及對－異構物之雙方)、二乙烯基聯苯(包含各異構物)及二乙烯基萘(包含各異構物)。更佳有，二乙烯基苯(間－及對－異構物之雙方)、二乙烯基聯苯(包含各異構物)。以使用二乙烯基苯(間－及對－異構物之雙方)最為適合。
單乙烯基芳香族化合物，除苯乙烯、乙烯基萘、乙烯基聯苯等以外，尚有此等之衍生物。衍生物，除芳香環被烷基、烷氧基、鹵素、苯基等取代基取代之化合物以外，尚有乙烯基之α位或β位被上述取代基取代的化合物。其他，茚、苊烯等芳香族烯烴及其衍生物，亦可作為單乙烯基芳香族化合物使用。此等可單獨或兩種以上組合使用。
苯乙烯衍生物，例如可使用甲基苯乙烯、乙基苯乙烯、丙基苯乙烯、丁基苯乙烯、戊基苯乙烯、己基苯乙烯、環己基苯乙烯、乙氧基苯乙烯、丙氧基苯乙烯、丁氧基苯乙烯、戊氧基苯乙烯、己氧基苯乙烯、環己氧基苯乙烯、苯氧基苯乙烯等。此等之取代基，相對於乙烯基，可在鄰－、間－或對－位取代；具有側鏈之情況，可為直鏈或支鏈狀之烷基或烷氧基。
茚或其衍生物，例如可使用茚、碳數1~6之烷基取代茚、碳數1~6之烷氧基取代茚等。苊烯或其衍生物有，例如苊烯、碳數1~6之烷基取代苊烯、苯基取代苊烯、氯、溴等鹵素取代苊烯等。
單乙烯基芳香族化合物，並非限定於此等。此等單乙烯基芳香族化合物之中，從聚合時共聚物之骨架中茚滿結構之生成量大的觀點而言，以烷基取化芳香族乙烯基化合物、α－烷基取代芳香族乙烯基化合物為佳。較佳之具體例，從成本及所得聚合物之耐熱性的觀點而言，有乙基乙烯基苯(間－及對－異構物之雙方)、乙基乙烯基聯苯(包含各異構物)及乙基乙烯基萘(包含各異構物)。
可溶性芳香族共聚物(A)，係將上述之二乙烯基芳香族化合物與單乙烯基芳香族化合物共聚合而得，因應需求可使用其他之單體。如此之其他的單體有，三乙烯基芳香族化合物或丁二烯、異戊二烯等二烯化合物、烷基乙烯基醚、異丁烯、二異丁烯等。此等其他之單體，在全單體之未達30莫耳%的範圍內使用。還有，二乙烯基芳香族化合物，係使用全單體之20莫耳%以上，較佳為40~80莫耳%；單乙烯基芳香族化合物，使用全單體之10莫耳%以上，較佳為20~60莫耳%。
製造可溶性芳香族共聚物(A)之聚合方法，以專利文獻8記載的方法為較佳之例。例如，下述之方法。
在有機溶劑中，藉由路易斯酸及下述一般式(1)所示之引發劑，將含有20~100莫耳%之二乙烯基芳香族化合物(a)所成的單體成份，於20~120℃之溫度進行陽離子聚合。
有機溶劑，以介電常數為2~15之一種以上的有機溶劑為佳；以存在選自季銨鹽、碳數3以上之醚系化合物、碳數3以上之硫醚系化合物及碳數2以上之亞碸系化合物所成群之施體成份為佳。有機溶劑，本質上為不妨礙陽離子聚合之化合物時，沒有特別的限制均可使用，在介電常數為2~15之範圍內，可單獨或兩種以上組合作為聚合溶劑使用。有機溶劑有氯化甲基、二氯甲烷、正丙基氯化物、正丁基氯化物、氯甲烷、三氯甲烷、四氯甲烷、氯乙烷、二氯乙烷、三氯乙烷、四氯乙烷、氯乙烯、二氯乙烯、氯苯、二氯苯、三氯苯等鹵化烴類；苯、甲苯、二甲苯、乙基苯、丙基苯、丁基苯等芳香族烴；乙烷、丙烷、丁烷、戊烷、己烷、庚烷、辛烷、壬烷、癸烷等直鏈式脂肪族烴類；2－甲基丙烷、2－甲基丁烷、2,3,3－三甲基戊烷、2,2,5－三甲基己烷等支鏈式脂肪族烴類；環己烷、甲基環己烷、乙基環己烷等環式脂肪族烴類；將石油餾份氫化精製之石臘油等。其中以二氯乙烷、甲苯、二甲苯、戊烷、己烷、庚烷、辛烷、2一甲基丙烷、2－甲基丁烷、甲基環己烷及乙基環己烷為佳。從聚合性、溶解性之平衡與取得之容易度的觀點而言，以二氯乙烷、甲苯、二甲苯、正己烷、環己烷、庚烷、甲基環己烷及乙基環己烷更適合。有機溶劑之使用量，考量所得聚合物溶液之黏度或除熱之容易度，通常決定於使聚合物之濃度為1~50wt%，較佳為5~35wt%。介電常數未達2時，聚合活性降低，甚不適合；介電常數超過15時，聚合之際容易造成凝膠化，極不適合。又，聚合係以將一般式(1)所示之引發劑、與相對於引發劑1莫耳為0.001~100莫耳，較佳為0.3~50莫耳之路易斯酸、及0.001~10莫耳之範圍的施體成份，在溶解可溶性芳香族共聚物之有機溶劑中，進行聚合為佳。
作為聚合催化劑使用之路易斯酸催化劑的具體例有，溴化硼(III)、氯化硼(III)、溴化鋁(III)、氟化鉑(III)、氯化鋁(III)、碘化鋁(III)、溴化鎵(III)、氯化鎵(III)、溴化銦(III)、氯化銦(III)、氟化銦(III)、碘化銦(III)、溴化鉈(III)、氟化鉈(III)、溴化矽(IV)、氯化矽(IV)、氟化矽(IV)、碘化矽(IV)、溴化鍺(IV)、氯化鍺(IV)、碘化鍺(IV)、溴化錫(IV)、氯化錫(IV)、氟化錫(IV)、碘化錫(IV)、氟化鉛(IV)、溴化銻(IV)、氯化銻(III)、氯化銻(V)、氟化銻(III)、氟化銻(V)、碘化銻(III)、溴化鉍(III)、氯化錫(III)、氟化鉍(III)、碘化鉍(III)、氯化鈦(IV)、溴化鈦(IV)、BF3
．OEt2
、氯化鎢(VI)、氯化釩(V)、氯化鐵(III)、溴化鋅(II)等金屬鹵化物；Et2
AlCl、EtAlCl2
等有機金屬鹵化物等。上述之催化劑，沒有特別的限制，可單獨或兩種以上組合使用。上述之催化劑中，從支鏈結構之控制、及聚合活性之觀點而言，以溴化硼(III)、氯化硼(III)、氯化錫(IV)、溴化錫(IV)、氟化錫(IV)、碘化錫(IV)、氯化銻(V)為佳。更佳為氯化硼(III)、氯化錫(IV)，以氯化錫(IV)最為適合。
一般式(1)所示之引發劑有，(1－氯－1－甲基乙基)苯、1,4－雙(1－氯－1－甲基乙基)苯、1,3－雙(1－氯－1－甲基乙基)苯、1,3,5－三(1－氯－1－甲基乙基)苯、1,3－雙(1－氯－1－甲基乙基)－5－(叔丁基)苯、1－氯乙基苯、1－溴乙基苯等化合物。較佳為，雙(1－氯－1－甲基乙基)苯、1－氯乙基苯及1－溴乙基苯。
製造可溶性芳香族共聚物(A)之聚合，係在20~100℃之溫度範圍進行。於未達20℃進行聚合反應時，所生成之共聚物的耐熱性低，甚不適合；又，超過100℃時，反應速度過大，反應之控制難以進行，容易生成交聯之不溶性的凝膠，極不適合。聚合反應停止後，回收共聚物之方法沒有特別的限制，例如蒸汽汽提法，亦可採用以弱溶劑析出等通常使用的方法。
可溶性芳香族共聚物(A)，以具有來自下述式(a2)所示之單乙烯基芳香族化合物的結構單位為佳；
(式中，R4
為碳數6~30之芳香族烴基)。
式(a1)所示之結構單位、與式(a2)所示之結構單位的存在莫耳比(a1)/[(a1)＋(a2)]為0.1以上。以0.3以上較佳，以0.5以上最適合。未達0.1時，記錄之全像與時間同時消失。
進而，可溶性芳香族共聚物(A)，其主鏈骨架中以具有0~20莫耳%之下述一般式(2)所示的茚滿結構單位為佳。
可溶性芳香族共聚物(A)之數平均分子量(採用凝膠滲透色譜法所得換算為標準聚苯乙烯。以下簡稱Mn)以400~30,000為佳。較佳為400~10,000，更佳為500~5,000。Mn未達400時，共聚物(A)之黏度過低、加工性不良，極不適合。又，Mn為30,000以上時，妨礙全像記錄時之快速的物質移動，甚不適合。
又，可溶性芳香族共聚物(A)分子量分佈(Mw/Mn)之值以10以下為佳。Mw/Mn超過10時，有可溶性多官能乙烯基芳香族共聚物之加工特性惡化，產生凝膠等之間題，很不適合。
可溶性芳香族共聚物(A)，具有具不飽鍵之式(a1)所示的結構單位之故，而具有聚合性。又可溶於甲苯、二甲苯、四氫呋喃、二氯乙烷或氯仿之故，可移動將組成物之特定部份聚合時濃度梯度之解除。
其次，就光自由基聚合性化合物(B)予以說明。
本發明所使用之光自由基聚合性化合物(B)，與可溶性芳香族共聚物(A)及後述之高分子結合劑(D)或增塑劑(E)之相溶性良好，可藉由自由基聚合引發劑產生之活性自由基種進行聚合。較佳為使用分子內至少具有一個(甲基)丙烯醯基、乙烯基、烯丙基等可聚合之官能基的單體。光自由基聚合性化合物(B)，可使用聚合性或折射率不同之兩種以上的光自由基聚合性化合物。
照射光時，首先聚合之成份(在干擾光之明亮部)，係以光自由基聚合性化合物(B)與可溶性芳香族共聚物(A)為主。此時生成之硬化物，推定係以可溶性芳香族共聚物(A)之聚合物、與光自由基聚合性化合物(B)與可溶性芳香族共聚物(A)之共聚物為主成份所成。但，在可溶性芳香族共聚物(A)之不存在系、或使用不具反應性乙烯基的芳香族低聚物替代可溶性芳香族共聚物(A)之系，雖瞬間記錄，其後放置不久記錄隨即消失之故，推測可溶性芳香族共聚物(A)，係與光自由基聚合性化合物(B)反應，擔當使記錄固定化之任務。因此，在下述之成份間產生折射率差。
(1)使用高分子結合劑(D)、增塑劑(E)或兩者之情況，明亮部係可溶性芳香族共聚物(A)與光自由基聚合性化合物(B)之硬化物被濃縮(硬化物濃縮相)，陰暗部係高分子結合劑(D)、增塑劑(E)或兩者被濃縮(非硬化物濃縮相)，而產生折射率差。
使用2種以上之光自由基聚合性化合物(B)，使用與在明亮部反應者比較反應性較差之光自由基聚合性化合物(B2)的情況，陰暗部係光自由基聚合性化合物(B2)之聚合物，與高分子結合劑(D)、增塑劑(E)或兩者被濃縮(暗硬化物及非硬化物濃縮相)，產生折射率差。所以(1)之情況，硬化物濃縮相與非硬化物濃縮相，折射率必要有一定值以上之差異。(2)之情況，硬化物濃縮相與暗硬化物及非硬化物濃縮相，折射率必要有一定值以上差異。折射率之調整，係藉由選擇光自由基聚合性化合物(B)、高分子結合劑(D)、增塑劑(E)之種類或量而成。
光自由基聚合性化合物(B)之例有，(甲基)丙烯酸甲酯、(甲基)丙烯酸丁酯、(甲基)丙烯酸2－乙基己基酯、(甲基)丙烯酸(十二)烷基酯、乙基卡必醇(甲基)丙烯酸酯、(甲基)丙烯酸苯氧基乙基酯、(甲基)丙烯酸壬基苯氧基乙基酯、(甲基)丙烯酸二環戊烯基酯、(甲基)丙烯酸異冰片烷基酯、(甲基)丙烯酸三溴苄基酯、丙烯醯基嗎啉等一官能(甲基)丙烯酸酯類；(甲基)丙烯氧基丙基三甲氧基矽烷等含矽(甲基)丙烯酸酯類；雙酚F、雙酚A、氫化雙酚A等雙酚化合物環氧烷加成物之二(甲基)丙烯酸酯類；三羥甲基丙烷三(甲基)丙烯酸酯、二季戊四醇五丙烯酸酯、季戊四醇三丙酸酯、季戊四醇四丙烯酸酯、二(三羥甲基)四丙烯酸酯、二季戊四醇六丙烯酸酯等多官能(甲基)丙烯酸酯；乙二醇二環氧丙基醚－環氧(甲基)丙烯酸酯、丙二醇二環氧丙基醚－環氧二(甲基)丙烯酸酯、苯酚環氧丙基醚－環氧(甲基)丙烯酸酯、間苯二酚二環氧丙基醚－環氧(甲基)丙烯酸酯、雙酚A二環氧丙基醚－環氧二(甲基)丙烯酸酯、雙(4－羥基苯基)硫化物二環氧丙基醚－環氧(甲基)丙烯酸酯、苯酚酚醛型環氧樹脂－(甲基)丙烯酸酯、甲酚酚醛型環氧樹脂－(甲基)丙烯酸酯、雙酚(例如雙酚A、雙酚F等)型環氧樹脂－(甲基)丙烯酸酯、聯酚(例如3,3',5,5'－四甲基聯酚等)型環氧樹脂－(甲基)丙烯酸酯、三(2,3環氧丙基)三聚異氰酸酯－(甲基)丙烯酸酯等各種眾所周知的環氧化合物與(甲基)丙烯酸之反應物的環氧(甲基)丙烯酸酯類；N,N－二甲基丙烯醯胺、N,N－二乙基丙烯醯胺等丙烯醯胺類；乙烯基苯、二乙烯基苯、乙烯基萘、乙烯基聯苯、苊烯、苯乙烯、對－氯苯乙烯、N－乙烯基咔唑、N－乙烯基吡咯烷酮、N－乙烯基己內醯胺等一官能之乙烯基化合物類；二亞丙烯基季戊四醇、二烯丙基苯二甲酸酯、二烯丙基異苯二甲酸酯、乙二醇二烯丙基碳酸酯、偏苯三酸三烯丙基酯、三烯丙基三聚(異)氰酸酯等含烯丙基化合物類；或、胺基甲酸酯(甲基)丙烯酸酯類、聚胺基甲酸酯(甲基)丙烯酸酯類、硫代胺基甲酸酯丙烯酸酯類、聚硫代胺基甲酸酯丙烯酸酯類、酯丙烯酸酯類、聚酯(甲基)丙烯酸酯類、聚醚(甲基)丙烯酸酯類、含硫(甲基)丙烯酸酯類、含硫多官能(甲基)丙烯酸酯類等眾所周知的各種聚合性單體或此等之低聚物，其他，各種光聚合性低聚物等。上述之中，以光硬化性較佳之(甲基)丙烯酸酯系單體為佳。含有至少二官能以上之(甲基)丙烯酸酯的(甲基)丙烯酸酯之組合，全像記錄性更為良好。
光自由基聚合性化合物(B)，係配合於組成物中，藉由照射光而聚合硬化，一部份係與可溶性芳香族共聚物(A)共聚合而硬化。
其次，就光聚合引發劑系(C)予以說明。
光聚合引發劑系(C)、吸收He－Ne雷射(633nm)、Ar雷射(515、488nm)、YAG雷射(532nm)、He－Cd雷射(442nm)、或藍色DPSS雷射(405nm)等可見光雷射光而產生自由基；以其活性自由基種使本發明之必要成份的可溶性芳香族共聚物(A)及光自由基聚合性化合物(B)進行聚合之引發劑系為佳。又，為更提高在各雷射光波長之感度的目的可添加色素增感劑。
光聚合引發劑有，例如2,2－二乙氧基苯乙酮、2,2－二乙氧基－2－苯基苯乙酮、二苯甲酮、1－(4－異丙基苯基)－2－羥基－2－甲基丙烷－1－酮、2－羥基－2－甲基－1－苯基丙烷－1－酮、苯偶姻乙基醚、苯偶姻異丁基醚、苯偶姻異丙基醚、1－羥基環己基苯基酮、2,2－二甲氧基－1,2－二苯基乙烷－1－酮、2－羥基－2－甲基－1－苯基丙烷－1－酮、1－(4－羥基乙氧基)－苯基－2－羥基－2－甲基－1－丙烷－1－酮、2－甲基－1－(4－甲硫基苯基)－2－嗎啉代丙烷－1－酮、2－苄基－2－二甲基胺基－1－(4－嗎啉代苯基)－丁酮－1、雙(2,4,6－三甲基苯甲醯基)－苯基膦氧化物、雙(2,6－二甲氧基苯甲醯基)－2,4,4－三甲基戊基膦氧化物、2,4,6－三甲基苯甲醯基－二苯基膦氧化物、雙(η 5－2,4－環戊二烯－1－基)－雙[2,6－二氟－3－(1H－吡咯－1－基)苯基]鈦、4,4－雙二甲基胺基二苯甲酮、甲基苯并異甲酸酯、苄基二甲基縮酮、苯甲醯基苯甲酸、4－二甲基胺基苯甲酸乙酯、2－氯噻噸酮、2－甲基噻噸酮、2,4－二乙基噻噸酮、2,4－二甲基噻噸酮、莰醌、二苯基乙二酮、4,4'－二乙基胺基二苯甲酮等。光自由基聚合引發劑之市售品有，例如依加魯丘爾(Irgacure 184、369、500、651、819、907、784、2959、達洛丘爾(Darocurl 1116、1173(以上均為吉巴特殊化學品股份有限公司製)等。
又，能以與上述光聚合引發劑併用之形態使用熱聚合引發劑。併用之熱聚合引發劑有，例如2,2'－偶氮雙(2－甲基丁腈)、2,2'－偶氮雙異丁腈、2,2'－偶氮雙異戊腈、2,2'－偶氮雙(2,4－二甲基戊腈)、1,1'－偶氮雙(環己烷－1－腈)、甲乙酮過氫化物、甲異丁酮過氧化物、苯甲醯基過氧化物、2,4－二氯苯甲醯基過氧化物等。
此等引發劑之添加量，依引發劑之種類，所配合之化合物的種類及組成比而異，不能一概決定；相對於感光樹脂組成物全量，以0.05~30重量%之範圍為佳。以0.1~8重量%之範圍更佳。未達0.05重量%時，硬化性劣化，殘留未反應物，以致記錄穩定性不良。又，超過30重量%時，聚合度降低，硬化物過度柔軟，隨情況而異透明性下降，甚不適合。為0.1~8重量%之情況，可賦予硬化性特別良好，且全像特性優異的感光樹脂組成物。
使用色素增感劑之情況，色素增感劑以在可見區域之光顯示吸收者為佳。有(噻)噸酮系色素、菁系色素、份菁系色素、斯庫瓦利利姆系色素、吉歐皮利利姆鹽系色素、喹啉系色素、(基底)苯乙烯基系色素、(縮酮)香豆素系色素、繞丹菁系色素、卟啉系色素、噁嗪系色素等眾所周知的化合物。此等可單獨或兩種以上組合使用。
本發明中，為提升例如可對應於厚膜之成膜性或膜強度、或提高全像記錄後的耐環境性等目的，可使用高分子結合劑(D)。以此目的使用之高分子結合劑(D)，較佳為透明性高、與可溶性芳香族共聚物(A)之相溶性高者。例如聚苯乙烯及其衍生物、甲基丙烯酸甲酯－苯乙烯共聚物(MS樹脂)、苯乙烯－丙烯腈共聚物(AS、SAN樹脂)、聚(4－甲基戊烯－1)(TPX樹脂)、聚環烯烴(COP樹脂)、聚二乙二醇雙烯丙基碳酸酯(EGAC樹脂)、聚硫代胺基甲酸酯(PTU樹脂)、聚甲基乙烯基醚(PMVE樹脂)、聚碸樹脂、聚乙酸乙烯酯、聚乙烯醇、聚乙烯吡咯烷酮、乙醯基纖維素等。高分子結合劑(D)，以其側鏈或主鏈上具有陽離子聚合性基等反應性基為佳。此等可配合一種以上。
本發明中，可使用增塑劑(E)作為提升可溶性芳香族共聚物(A)、光自由基聚合性化合物(B)之物質移動、或感光性樹脂組成物之相溶性的化合物。增塑劑(E)適合選擇，與芳香族共聚物(A)及光自由基聚合性化合物(B)之相溶性高者，進而容易使記錄時之物質移動的液狀者。例如可使用二甲基癸二酸酯、二乙基癸二酸酯、二丁基癸二酸酯、雙(2－乙基己基)癸二酸酯等癸二酸酯類；二甲基己二酸酯、二乙基己二酸酯、二丁基己二酸酯、雙(2－乙基己基)己二酸酯等己二酸酯類；二甲基苯二甲酸酯、二乙基苯二甲酸酯、二丁基苯二甲酸酯、雙(2－乙基己基)苯二甲酸酯、二異癸基苯二甲酸酯等苯二甲酸酯類；三甲基磷酸酯、三乙基磷酸酯、三丁基磷酸酯、三(2－乙基己基)磷酸酯、三苯基磷酸酯、甲酚基二苯基磷酸酯、三甲酚基磷酸酯等正磷酸酯類；等眾所周知的增塑劑(E)。此等可一種以上使用。
進而，因應需求可添加熱聚合抑制劑、鏈移動劑、抗氧化劑、矽烷偶合劑、塗面改善劑、表面調整劑、增塑劑、消泡劑、界面活性劑、著色劑、儲存穩定劑、吸收紫外線劑、增黏劑等其他之眾所周知的添加劑(F)。
本發明之樹脂組成物為固體的情況、或高黏度難以塗佈之情況，可使用將樹脂組成物溶解或分散之溶劑(G)。有例如丙酮、甲乙酮、甲異丁酮、環己酮等酮類；乙酸乙酯、乙酸丁酯等酯類；甲苯、二甲苯等石油系溶劑；甲基溶纖劑、乙基溶纖劑、丁基溶纖劑等溶纖劑類；乙醇、甲醇、異丙醇、丁醇等醇類；四氫呋喃、二噁烷等醚類；二氯甲烷、氯仿等鹵化烴等。溶劑，相對於樹脂固形成份100重量份，以配合200重量份以下為佳，以100重量份以下更佳。又，為提高後述之乾燥步驟的效率，其沸點以100℃以下者為佳。還有，溶劑(G)係使樹脂組成物溶解成或分散之成份，並非本發明之樹脂組成物的構成成份，於各成份之含量的計算時應予以除外。
還有，本發明之組成物中作用必要成份使用的成份為(A)~(C)、與(D)或(E)，以使用(D)及(E)之兩者為佳。又，在上述成份及其他成份(F)等，以及溶劑(G)之說明中，並非限定於例示者。
本發明之體積相位型全像記錄用感光性樹脂組成物，相對於組成物全重量(溶劑除外)，各成份以下述之比例配合為佳。
可溶性芳香族共聚物(A)為5~60重量%，較佳為10~40重量%。
光自由基聚合性化合物(B)為5~50重量%，較佳為10~40重量%。
光聚合引發劑(C)為0.05~30重量%，較佳為1~10重量%(配合色素增感劑之情況，色素增感劑為0.01~10重量%，與光聚合引發劑之合計量不超過30重量%)。
高分子結合劑(D)為0~50重量%，較佳為10~40重量%。
增塑劑(E)為0~40重量%，較佳為10~35重量%。
高分子結合劑(D)與增塑劑(E)之合計為20~80重量%，較佳為30~70重量%。
由本發明之感光性樹脂組成物製作全像記錄用媒體，係採用旋轉塗佈機、滾筒塗佈機、棒桿塗佈機等眾所周知的塗佈設備，將液狀之感光性樹脂組成物塗佈於玻璃板或聚碳酸酯板、聚甲基丙烯酸甲酯板、聚酯薄膜等基材上至乾燥膜厚成為1~1000 μ m，因應需求經乾燥，製作全像記錄用媒體之方法較為適合。此時，可在感光性樹脂組成物層上設置作為氧遮斷膜之保護層。保護層，可使用例如與上述基板同等者，或聚烯烴、聚氯乙烯、聚偏氯乙烯、聚乙烯醇或聚對苯二甲酸乙二醇酯等薄膜或玻璃。還有，塗佈感光液之際，因應需求可使用適當的溶液稀釋；其情況，在塗佈於基板上之後，需要予以乾燥。
如上所述製成之記錄層，可藉由以往所知悉之方法進行干擾曝光，形成體積相位型全像。例如，採用通常之全像曝光裝置，以雷射光或同調性(可干擾性)優越之光(例如波長300~1200nm之光)，藉由二光束干擾條紋曝光，在其內部記錄干擾條紋。於此階段，藉由記錄之干擾條紋而得衍射光，可為全像。
適合於本發明之全像記錄材料的光源，可使用He－Ne雷射(633nm)、Ar雷射(515、488nm)、YAG雷射(522nm)、He－Cd雷射(442nm)、或藍色DPSS雷射(405nm)等。又，在以上述雷射等全像記錄後，藉由氙氣燈、水銀燈、金屬鹵化物燈等之紫外線(UV)全面照射、或60℃程度之熱，加於光記錄用組成物膜，促進未反應而殘留之一部份自由基聚合性化合物的聚合，隨物質移動之相分離，可獲得全像特性更優越的全像。
依本發明，藉由感光性樹脂組成物中使用可溶性多官能乙烯基芳香族共聚物，可提供感度、低硬化收縮率、透明性優異之體積相位型全像記錄材料、及體積相位型全像記錄媒體、以及體積相位型全像。
以實施例具體說明本發明如下。本發明並非限定於此等實施例者。還有，實施例中使用的符號如下述之說明。
DVB：二乙烯基苯DVB507：DVB與乙基乙烯基苯之成份比為57：43之混合單體(新日鐵化學公司製)、S2EG：雙(2－甲基丙烯醯基乙硫基)硫化物(住友精化公司製)、TCP：三甲酚基磷酸酯(新日本理化公司製)、MS－200：甲基丙烯酸甲酯－苯乙烯(20：80)共聚物、MS－600：甲基丙烯酸甲酯－苯乙烯(60：40)共聚物。
還有，本實施例中全像及感光性樹脂組成物之評估以下述之方法進行。
(衍射效率之評估)透過型全像之衍射效率，係採用以光功率計讀取直線偏光型He－Ne雷射(632.8nm)的衍射光之值，由下式算出。
衍射效率(%)＝(衍射光強度/射入光強度)×100
(耐環境性之評估)記錄1個月後(於60℃儲存)之衍射效率、透明性之變化(○：無改變、△：略改變、×：有改變)。
(感光性樹脂組成物之體積收縮率)感光性樹脂組成物之硬化收縮率，係藉由測定硬化前後之樹脂組成物的密度，以下式算出。還有，光源使用點UV照射裝置，相對於50 μ m厚度之試料，於空氣下照射6mW/cm2
之UV。
硬化收縮率(%)＝(1－液密度/薄膜密度)×100
將二乙烯基苯1.75莫耳(258.9ml)、乙基乙烯基苯1.30莫耳(186.3ml)、1－氯乙基苯(289.1mmol)之甲苯溶液2282ml(甲苯1806ml、莫耳濃度：1.31mol/ml、介電常數：2.38)，投入3000ml之燒瓶內，加熱至30℃。進而，添加12.64mmol之SnCl4
的甲苯溶液21.7ml(濃度：0.584mmol/ml)，反應4小時。聚合反應以氮氣進行冒泡，使用少量之甲醇停止後，在室溫下將反應混合物投入大量之甲醇中，析出可溶性芳香族共聚物。將所得共聚物以甲醇洗淨，經過濾、乾燥、秤量，即得可溶性芳香族共聚物171.62g(收率：42.9wt%)。聚合活性為3.39(g聚合物/mmol Sn．小時)。所得共聚物之Mw為6930，Mn為1990，Mw/Mn為3.48。
將二乙烯基苯1.51莫耳(223.4ml)、乙基乙烯基苯0.71莫耳(123.2ml)、1－氯乙基苯(364.2mmol)之二氯乙烷溶液5.5ml(濃度：0.73mmol/ml)及二氯乙烷3500ml(介電常數：10.3)，投入5000ml之燒瓶中，於70℃添加50.11mmol之SnCl4
的二氯乙烷溶液(濃度：0.074mmol/ml)63.3ml，反應3小時。聚合反應以氮氣進行冒泡，使用少量之甲醇停止後，在室溫下將反應混合物投入大量之甲醇中，析出可溶性芳香族共聚物。將所得共聚物以甲醇洗淨，經過濾、乾燥、秤量，即得可溶性芳香族共聚物178.91g(收率：61.3wt%)。聚合活性為8.54(g聚合物/mmol Sn．小時)。所得共聚物之Mw為49,700，Mn為9730，Mw/Mn為5.1。
配合下述說明之成份，製成體積相位型全像記錄用感光性樹脂組成物溶液。
在二氯甲烷50g中，溶解合成例1所得共聚物10g、TCP：15g、MS－200：20g、S2EG：15g、1－羥基環己基苯基酮(Irgacure 184，吉巴特殊化學品股份有限公司製)0.1g、3－乙基－5－[(3－乙基－2－(3H)－苯并噻唑基)亞乙基]－2－硫代－4－噁唑烷酮(NK－1473，林原生物化學研究所股份有限公司製)0.01g，即得感光液。
使用棒桿塗佈機，將其塗佈於50mm×50mm×厚度0.5mm之玻璃基板的單面上至乾燥膜厚為50 μ m，在設定於50℃之氮氣氣體環境的惰性爐中乾燥1小時，即製成體積相位型全像記錄用感光板。於其上層壓保護膜之38 μ m的PET薄膜，即得光資訊記錄媒體。
所得記錄媒體藉由氬離子雷射之514.5nm光，採用二光束干擾曝光法，
作為空間頻率約1000條/mm之干擾條紋，將其自PET側射入，即記錄體積相位型全像。透過型全像之曝光，係在感光板上之一個光強度為1mW/cm2
，10~100秒鐘，以曝光量10~100mJ/cm2
進行。所得體積相位型全像，於曝光量13mJ/cm2
之衍射效率為82%。又，樹脂組成物之硬化收縮率為0.5%。
除配合組成如表1所示以外，其他與實施例1同樣進行，製成感光性樹脂組成物溶液，由其而得光資訊記錄媒體，記錄全像，進行評估。組成及評估結果如表1所示。表1中，DVB低聚物(Mn＝2000)為合成例1所得之共聚物；DVB低聚物(Mn＝10,000)為合成例2所得共聚物。
Claims (5)
- 一種體積相位型全像記錄用感光性樹脂組成物，其係包含可溶性芳香族共聚物(A)、可與可溶性芳香族共聚物(A)共聚合之光自由基聚合性化合物(B)、與高分子結合劑(D)、及/或增塑劑(E)而成之感光性樹脂組成物，其特徵為包含該可溶性芳香族共聚物(A)5~60重量%，該可溶性芳香族共聚物(A)為具有二乙烯基芳香族化合物之結構單位與單乙烯基芳香族化合物之結構單位，且含有10莫耳%以上之下述式(a1)所示之結構單位；
- 如申請專利範圍第1項之體積相位型全像記錄用感光性樹脂組成物，其中可溶性芳香族共聚物(A)之數平均分子量為400~30,000。
- 一種體積相位型全像記錄用光資訊記錄媒體，其特徵為由申請專利範圍第1項或第2項之感光性樹脂組成物所成之記錄層，係形成於一個支撑體上或兩個支撑體間所成。
- 一種體積相位型全像，其特徵為在如申請專利範 圍第3項之光資訊記錄媒體上，進行記錄由同調性優越之能量線所形成之干擾條紋而得。
- 一種體積相位型全像之製造方法，其特徵為在如申請專利範圍第3項之記錄媒體上，予以曝光記錄由同調性優越之能量線所形成之干擾條紋。
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| JP5647808B2 (ja) | 2010-03-30 | 2015-01-07 | 富士フイルム株式会社 | レンズアレイのマスタの製造方法 |
| JP5533249B2 (ja) * | 2010-05-20 | 2014-06-25 | Ｔｄｋ株式会社 | 体積型ホログラム記録材料及び体積型ホログラム記録媒体 |
| TWI507425B (zh) * | 2010-06-14 | 2015-11-11 | Nippon Steel & Sumikin Chem Co | An ultraviolet-curing resin composition for use in an ink-jet printing method, and an optical element |
| JP5569316B2 (ja) * | 2010-10-04 | 2014-08-13 | Ｔｄｋ株式会社 | ホログラム記録材料及びホログラム記録媒体 |
| JP5181056B2 (ja) * | 2011-11-28 | 2013-04-10 | 新日鉄住金化学株式会社 | ハードコートフィルム又はシート、光学素子及び画像表示装置 |
| CN102854747B (zh) * | 2012-09-28 | 2017-06-06 | 乐凯华光印刷科技有限公司 | 版材表面粘性小的柔性感光树脂版 |
| WO2019131572A1 (ja) | 2017-12-26 | 2019-07-04 | 富士フイルム株式会社 | レンズ用接着剤、接合レンズ、および撮像モジュール |
| KR102239212B1 (ko) * | 2018-12-14 | 2021-04-12 | 주식회사 엘지화학 | 포토폴리머 조성물 |
| KR102255555B1 (ko) * | 2019-08-20 | 2021-05-25 | 울산과학기술원 | 디더링 마스크를 이용한 홀로그래픽 패턴 발현 유기젤의 제조방법 |
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| TWI220938B (en) * | 2001-02-01 | 2004-09-11 | Nat Inst Of Advanced Ind Scien | Hologram recording material composition, hologram recording medium and process for producing same |
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| JP4325404B2 (ja) * | 2002-03-27 | 2009-09-02 | ダイソー株式会社 | ホログラム記録材料用フォトポリマー組成物、ホログラム記録媒体およびその製造方法 |
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- 2006-03-01 CN CN2006800074140A patent/CN101137940B/zh not_active Expired - Fee Related
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- 2006-03-01 WO PCT/JP2006/303832 patent/WO2006095610A1/ja active Application Filing
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| Publication number | Priority date | Publication date | Assignee | Title |
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| TWI220938B (en) * | 2001-02-01 | 2004-09-11 | Nat Inst Of Advanced Ind Scien | Hologram recording material composition, hologram recording medium and process for producing same |
| JP2004123873A (ja) * | 2002-10-01 | 2004-04-22 | Nippon Steel Chem Co Ltd | 可溶性多官能ビニル芳香族共重合体及びその重合方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20070108947A (ko) | 2007-11-13 |
| CN101137940B (zh) | 2010-08-25 |
| KR101024744B1 (ko) | 2011-03-25 |
| WO2006095610A1 (ja) | 2006-09-14 |
| CN101137940A (zh) | 2008-03-05 |
| TW200702915A (en) | 2007-01-16 |
| JPWO2006095610A1 (ja) | 2008-08-14 |
| JP4745333B2 (ja) | 2011-08-10 |
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