JP2010084148A - ホログラフィック媒体を製造するための特定のポリエーテル系ポリウレタン組成物 - Google Patents
ホログラフィック媒体を製造するための特定のポリエーテル系ポリウレタン組成物 Download PDFInfo
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- JP2010084148A JP2010084148A JP2009226491A JP2009226491A JP2010084148A JP 2010084148 A JP2010084148 A JP 2010084148A JP 2009226491 A JP2009226491 A JP 2009226491A JP 2009226491 A JP2009226491 A JP 2009226491A JP 2010084148 A JP2010084148 A JP 2010084148A
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- acrylate
- polyurethane composition
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- meth
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- 239000000203 mixture Substances 0.000 title claims abstract description 99
- 239000004814 polyurethane Substances 0.000 title claims abstract description 54
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 49
- 239000004721 Polyphenylene oxide Substances 0.000 title description 30
- 229920000570 polyether Polymers 0.000 title description 25
- 150000001875 compounds Chemical class 0.000 claims abstract description 55
- 229920000642 polymer Polymers 0.000 claims abstract description 25
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 21
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 21
- 239000012948 isocyanate Substances 0.000 claims abstract description 20
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 17
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 13
- 239000003381 stabilizer Substances 0.000 claims abstract description 7
- 230000009471 action Effects 0.000 claims abstract description 4
- 229920005862 polyol Polymers 0.000 claims description 53
- 150000003077 polyols Chemical class 0.000 claims description 53
- -1 oxyethylene, oxypropylene Chemical group 0.000 claims description 43
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 35
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 25
- 239000003054 catalyst Substances 0.000 claims description 23
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 22
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- 239000003999 initiator Substances 0.000 claims description 18
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- 239000004417 polycarbonate Substances 0.000 claims description 18
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 claims description 16
- 125000001931 aliphatic group Chemical group 0.000 claims description 15
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- 125000003118 aryl group Chemical group 0.000 claims description 12
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- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
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- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 claims description 6
- PJMDLNIAGSYXLA-UHFFFAOYSA-N 6-iminooxadiazine-4,5-dione Chemical group N=C1ON=NC(=O)C1=O PJMDLNIAGSYXLA-UHFFFAOYSA-N 0.000 claims description 6
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000005702 oxyalkylene group Chemical group 0.000 claims description 6
- 230000005855 radiation Effects 0.000 claims description 6
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 claims description 5
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 5
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 4
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- 239000000758 substrate Substances 0.000 claims description 4
- MHCLJIVVJQQNKQ-UHFFFAOYSA-N ethyl carbamate;2-methylprop-2-enoic acid Chemical compound CCOC(N)=O.CC(=C)C(O)=O MHCLJIVVJQQNKQ-UHFFFAOYSA-N 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
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- 229910052727 yttrium Inorganic materials 0.000 claims description 3
- WJIOHMVWGVGWJW-UHFFFAOYSA-N 3-methyl-n-[4-[(3-methylpyrazole-1-carbonyl)amino]butyl]pyrazole-1-carboxamide Chemical compound N1=C(C)C=CN1C(=O)NCCCCNC(=O)N1N=C(C)C=C1 WJIOHMVWGVGWJW-UHFFFAOYSA-N 0.000 claims 1
- 125000006353 oxyethylene group Chemical group 0.000 claims 1
- 239000011159 matrix material Substances 0.000 abstract description 16
- 239000000126 substance Substances 0.000 abstract description 14
- 239000000178 monomer Substances 0.000 abstract description 11
- 229920006030 multiblock copolymer Polymers 0.000 abstract description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 23
- 239000011521 glass Substances 0.000 description 22
- 239000000047 product Substances 0.000 description 22
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 21
- 229920005906 polyester polyol Polymers 0.000 description 18
- 239000000243 solution Substances 0.000 description 15
- 239000007788 liquid Substances 0.000 description 14
- 238000002156 mixing Methods 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- 150000005846 sugar alcohols Polymers 0.000 description 13
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 12
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 12
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 12
- ZFPGARUNNKGOBB-UHFFFAOYSA-N 1-Ethyl-2-pyrrolidinone Chemical compound CCN1CCCC1=O ZFPGARUNNKGOBB-UHFFFAOYSA-N 0.000 description 10
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 10
- 150000002009 diols Chemical class 0.000 description 10
- SQHOAFZGYFNDQX-UHFFFAOYSA-N ethyl-[7-(ethylamino)-2,8-dimethylphenothiazin-3-ylidene]azanium;chloride Chemical compound [Cl-].S1C2=CC(=[NH+]CC)C(C)=CC2=NC2=C1C=C(NCC)C(C)=C2 SQHOAFZGYFNDQX-UHFFFAOYSA-N 0.000 description 10
- 229920000728 polyester Polymers 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- 230000001588 bifunctional effect Effects 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
- 150000003254 radicals Chemical class 0.000 description 9
- 125000006850 spacer group Chemical group 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 125000002947 alkylene group Chemical group 0.000 description 8
- 230000005540 biological transmission Effects 0.000 description 8
- 125000005442 diisocyanate group Chemical group 0.000 description 8
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 7
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 7
- 150000002596 lactones Chemical class 0.000 description 7
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 6
- VZXPHDGHQXLXJC-UHFFFAOYSA-N 1,6-diisocyanato-5,6-dimethylheptane Chemical compound O=C=NC(C)(C)C(C)CCCCN=C=O VZXPHDGHQXLXJC-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 6
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 6
- 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 5
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 5
- 229920002521 macromolecule Polymers 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate group Chemical group C(C(=C)C)(=O)[O-] CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 5
- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 description 5
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 5
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 5
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- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 4
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- 238000007259 addition reaction Methods 0.000 description 4
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- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 4
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 4
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- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 3
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 3
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- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 3
- FGPCETMNRYMFJR-UHFFFAOYSA-L [7,7-dimethyloctanoyloxy(dimethyl)stannyl] 7,7-dimethyloctanoate Chemical compound CC(C)(C)CCCCCC(=O)O[Sn](C)(C)OC(=O)CCCCCC(C)(C)C FGPCETMNRYMFJR-UHFFFAOYSA-L 0.000 description 3
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 3
- 150000008065 acid anhydrides Chemical class 0.000 description 3
- 150000001414 amino alcohols Chemical class 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
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- 239000012975 dibutyltin dilaurate Substances 0.000 description 3
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 3
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- WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- FAQJJMHZNSSFSM-UHFFFAOYSA-N phenylglyoxylic acid Chemical compound OC(=O)C(=O)C1=CC=CC=C1 FAQJJMHZNSSFSM-UHFFFAOYSA-N 0.000 description 1
- 238000006303 photolysis reaction Methods 0.000 description 1
- 230000015843 photosynthesis, light reaction Effects 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920005646 polycarboxylate Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- INCIMLINXXICKS-UHFFFAOYSA-M pyronin Y Chemical compound [Cl-].C1=CC(=[N+](C)C)C=C2OC3=CC(N(C)C)=CC=C3C=C21 INCIMLINXXICKS-UHFFFAOYSA-M 0.000 description 1
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical compound C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 150000005839 radical cations Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- OARRHUQTFTUEOS-UHFFFAOYSA-N safranin Chemical compound [Cl-].C=12C=C(N)C(C)=CC2=NC2=CC(C)=C(N)C=C2[N+]=1C1=CC=CC=C1 OARRHUQTFTUEOS-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- SPVXKVOXSXTJOY-UHFFFAOYSA-O selenonium Chemical class [SeH3+] SPVXKVOXSXTJOY-UHFFFAOYSA-O 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical class O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 101150046896 trm1 gene Proteins 0.000 description 1
- JEVGKYBUANQAKG-UHFFFAOYSA-N victoria blue R Chemical compound [Cl-].C12=CC=CC=C2C(=[NH+]CC)C=CC1=C(C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1 JEVGKYBUANQAKG-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Images
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Abstract
【解決手段】A)ポリイソシアネート成分;B)1000g/mol超の数平均分子量を有するY(Xi−H)n型のヒドロキシ官能性マルチブロックコポリマーB1)を含んでなる、イソシアネート反応性成分;C)重合を介してエチレン性不飽和化合物と化学線の作用下で反応する基を含有するNCO基不含有化合物;D)ラジカル安定剤;およびE)光開始剤を含んでなるポリウレタン組成物。
【選択図】なし
Description
A)ポリイソシアネート成分;
B)1000g/mol超の数平均分子量を有するY(Xi−H)n型:
[ここで、Xiは式(I):
-CH2-CH(R)-O- (I)
で示されるオキシアルキレン単位であり、
iは1〜10の整数であり、
nは2〜8の整数であり、
Rは、水素、アルキルまたはアリール基であり、前記アルキルまたはアリール基は、ヘテロ原子によって任意に置換または中断されていてよく、
Yは基本開始剤であり、セグメントXiおよびYの総量に基づいたセグメントXiの割合は少なくとも50重量%を占める。]
のヒドロキシ官能性マルチブロックコポリマーB1)を含んでなる、イソシアネート反応性成分;
C)重合を介してエチレン性不飽和化合物と化学線の作用下で反応する基を含有するNCO基不含有化合物;
D)ラジカル安定剤;
E)光開始剤;
F)任意に触媒;および
G)任意に助剤および添加剤
を含んでなるポリウレタン組成物である。
A)ポリイソシアネート成分;
B)1000g/mol超の数平均分子量を有するY(Xi−H)n型[ここで、i=1〜10、およびn=2〜8である。]のヒドロキシ官能性マルチブロックコポリマーB1)を含んでなるイソシアネート反応性成分であって、セグメントXiが、いずれの場合にも式(I):
-CH2-CH(R)-O- (I)
[式中、Rは、水素、ヘテロ原子(例えばエーテル酸素)によって任意に置換または中断されていてよいアルキルまたはアリール基である。]
で示されるオキシアルキレン単位であり、Yが基本開始剤であり、セグメントXiおよびYの総量に基づいたセグメントXiの割合が少なくとも50重量%を占める、イソシアネート反応性成分;
C)重合を伴ってエチレン性不飽和化合物と化学線の作用下で反応する基(放射線硬化性基)を含有し、NCO基を含有しない化合物;
D)ラジカル安定剤;
E)光開始剤;
F)任意に触媒;
G)任意に助剤および添加剤
を含んでなるポリウレタン組成物に関する。
5〜93.999重量%の本発明の成分B)、
1〜60重量%の成分A)、
5〜70重量%の成分C)、
0.001〜10重量%の光開始剤E)、
0〜10重量%のラジカル安定剤D)、
0〜4重量%の触媒F)、
0〜70重量%の助剤および添加剤G)。
15〜82.989重量%の本発明の成分B)、
2〜40重量%の成分A)、
15〜70重量%の成分C)、
0.01〜7.5重量%の光開始剤E)、
0.001〜2重量%のラジカル安定剤D)、
0〜3重量%の触媒F)、
0〜50重量%の助剤および添加剤G)。
15〜82.489重量%の本発明の成分B)、
2〜40重量%の成分A)、
15〜50重量%の成分C)、
0.5〜5重量%の光開始剤E)、
0.01〜0.5重量%のラジカル安定剤D)、
0.001〜2重量%の触媒F)、
0〜35重量%の助剤および添加剤G)。
図1に示した測定装置を用い、実験の部で製造した本発明の媒体および比較媒体を、ホログラム特性について試験した。
照射時間tの間、両方のシャッター(S)を開放する。その後、シャッター(S)を閉じた状態で、媒体を5分間おいて、まだ重合されていない書込モノマーを拡散させた。ここで、書き込まれたホログラムを、以下の方法で読み込んだ。信号光線のシャッターは閉じたままであった。参照光線のシャッターを開放した。参照光線の虹彩絞りを1mm未満の直径まで閉じた。これにより、媒体の回転角(Ω)の全てにおいて、光線は、先に書き込まれたホログラムに常に完全に存在することが確実になった。コンピューター制御の下、回転台は、0.05°の角度ステップ幅でΩ=0°からΩ=20°まで角度範囲を変えた。各々の角度に近づくと、対応する検出器Dを用いて、ゼロ次透過された光線の出力を測定し、検出器Dを用いて、一次回折された光線の出力を測定した。以下の式:
まず、0.18gのオクタン酸亜鉛、374.8gのε−カプロラクトン、および374.8gの二官能性ポリテトラヒドロフランポリエーテルポリオール(500g/molのOH当量)を1リットル容のフラスコに導入し、120℃まで加熱し、固形分(不揮発性成分の割合)が99.5重量%以上になるまで、この温度で維持した。その後、冷却し、ワックス様固体として生成物を得た。
2465gのTerathane(登録商標)650を、撹拌機を備えた20リットル容の反応槽に計量添加し、450.5mgのDMC触媒を添加した。次いで、約70rpmで撹拌しながら105℃まで加熱した。真空および窒素での圧力平衡を3回適用することによって、空気を窒素に入れ換えた。撹拌速度を300rpmまで上昇させた後、真空ポンプを稼働させながら約0.1barの圧力で、下方より混合物を通して窒素を72分間流通させた。その後、窒素によって0.3barの圧力を確立し、242gのプロピレンオキシド(PO)を添加して重合を開始させた。それによって、圧力は2.03barまで上昇した。8分後、圧力は再び0.5barまで低下し、更なる12.538kgのPOを、2.34barで2時間11分にわたって計量添加した。POの計量添加が完了した17分後、1.29barの残圧で減圧を適用し、完全に脱気した。7.5gのIrganox 1076の添加によって生成物を安定化した。粘性のある無色の液体として、生成物を得た(OH価:27.8mgKOH/g、25℃での粘度:1165mPa・s)。
2475gのTerathane(登録商標)650を、撹拌機を備えた20リットル容の反応槽に計量添加し、452.6mgのDMC触媒を添加した。次いで、約70rpmで撹拌しながら105℃まで加熱した。真空および窒素での圧力平衡を3回適用することによって、空気を窒素に入れ換えた。撹拌速度を300rpmまで上昇させた後、真空ポンプを稼働させながら約0.1barの圧力で、下方より混合物を通して窒素を57分間流通させた。その後、窒素によって0.5barの圧力を確立し、100gのエチレンオキシド(EO)および150gのPOを同時に添加して重合を開始させた。それによって、圧力は2.07barまで上昇した。10分後、圧力は再び0.68barまで低下し、更なる5.116kgのEOおよび7.558kgのPOを混合物として、2.34barで1時間53分にわたって添加した。エポキシドの計量添加が完了した31分後、2.16barの残圧で減圧を適用し、完全に脱気した。7.5gのIrganox 1076の添加によって生成物を安定化した。粘性のある僅かに濁った(TE(F)値330)液体として、生成物を得た(OH価:27.1mgKOH/g、25℃での粘度:1636mPa・s)。
650g/molの数平均モル質量を有し、(3−メチル)−1,5−ペンタンジオールおよびジフェニルカーボネートの重縮合によって調製されたポリカーボネートジオール1707gを、撹拌機を備えた20リットル容の反応槽に計量添加し、527mgのDMC触媒を添加した。次いで、約70rpmで撹拌しながら130℃まで加熱した。真空および窒素での圧力平衡を3回適用することによって、空気を窒素に入れ換えた。撹拌速度を300rpmまで上昇させた後、真空ポンプを稼働させながら約0.1barの圧力で、下方より混合物を通して窒素を85分間流通させた。その後、窒素によって0.2barの圧力を確立し、174gのPOを添加して重合を開始させた。それによって、圧力は2.26barまで上昇した。6分後、圧力は再び0.55barまで低下し、更なる8.826kgのPOを、1.36barで1時間32分にわたって添加した。POの計量添加が完了した22分後、0.674barの残圧で減圧を適用し、完全に脱気した。5.27gのIrganox 1076の添加によって生成物を安定化した。粘性のある無色の液体として、生成物を得た(OH価:24.8mgKOH/g、25℃での粘度:1659mPa・s)。
まず、0.1gの2,6−ジ−tert−ブチル−4−メチルフェノール、0.05gのジラウリン酸ジブチル錫(Desmorapid Z, Bayer MaterialScience AG(ドイツ国レーフエルクーゼン在))、および213.07gの酢酸エチル中27%濃度トリス(p−イソシアナトフェニル)チオホスフェート溶液(Desmodur(登録商標)RFE, Bayer MaterialScience AG(ドイツ国レーフエルクーゼン在)の製品)を500ml容の丸底フラスコに導入し、60℃まで加熱した。次いで、42.37gの2−ヒドロキシエチルアクリレートを滴加し、イソシアネート含量が0.1%未満に低下するまで、混合物を60℃で維持した。その後、冷却し、酢酸エチルを真空下、完全に除去した。半結晶性固体として、生成物を得た。
8.89gの前記したように調製したポリオール1(成分Bに対する比較)を、3.75gのウレタンアクリレート1(成分C)、0.15gのCGI 909および0.015gのニューメチレンブルー(共成分E)と60℃で、並びに0.525gのN−エチルピロリドン(成分G)と混合し、透明溶液を得た。次いで、30℃まで冷却し、1.647gのDesmodur(登録商標)XP 2410(成分A)を添加し、再び混合した。最後に、0.009gのFomrez(登録商標)UL 28(成分F)を添加し、再び短く混合した。続いて、得られた液状物質をガラス板上に注ぎ、それを、スペーサーによって20μmの距離に保った第2のガラス板で覆った。この試験片を室温で放置し、16時間にわたって硬化させた。最大Δn:0.0101。
6.117gのポリオール2(成分Bに対する比較)を、3.75gのウレタンアクリレート1(成分C)、0.15gのCGI 909および0.015gのニューメチレンブルー(共成分E)と60℃で、並びに0.525gのN−エチルピロリドン(成分G)と混合し、透明溶液を得た。次いで、30℃まで冷却し、4.418gのBaytec(登録商標)WE180(成分A)を添加し、再び混合した。最後に、0.030gのFomrez(登録商標)UL 28(成分F)を添加し、再び短く混合した。続いて、得られた液状物質をガラス板上に注ぎ、それを、スペーサーによって20μmの距離に保った第2のガラス板で覆った。この試験片を室温で放置し、16時間にわたって硬化させた。最大Δn:0.0063。
7.342gのTerathane 1000(成分Bに対する比較)を、3.75gのウレタンアクリレート1(成分C)、0.15gのCGI 909および0.015gのニューメチレンブルー(共成分E)と60℃で、並びに0.525gのN−エチルピロリドン(成分G)と混合し、透明溶液を得た。次いで、30℃まで冷却し、3.193gのDesmodur(登録商標)XP 2580(成分A)を添加し、再び混合した。最後に、0.030gのFomrez(登録商標)UL 28(成分F)を添加し、再び短く混合した。続いて、得られた液状物質をガラス板上に注ぎ、それを、スペーサーによって20μmの距離に保った第2のガラス板で覆った。この試験片を室温で放置し、16時間にわたって硬化させた。最大Δn:0.0106。
1.129gのpolyether L800(200g/molの数平均モル質量を有するポリプロピレンオキシド)(成分Bに対する比較)を、3.081gのウレタンアクリレート1(成分C)、0.12gのCGI 909および0.012gのニューメチレンブルー(共成分E)と60℃で、並びに0.431gのN−エチルピロリドン(成分G)と混合し、透明溶液を得た。次いで、30℃まで冷却し、7.525gのDesmodur(登録商標)XP 2599(成分A)を添加し、再び混合した。最後に、0.0259gのFomrez(登録商標)UL 28(成分F)を添加し、再び短く混合した。続いて、得られた液状物質をガラス板上に注ぎ、それを、スペーサーによって20μmの距離に保った第2のガラス板で覆った。この試験片を室温で放置し、16時間にわたって硬化させた。最大Δn:0.0096。
8.293gのポリオール3(成分B)を、5.25gのウレタンアクリレート1(成分C)、0.15gのCGI 909および0.015gのニューメチレンブルー(共成分E)と60℃で、並びに0.525gのN−エチルピロリドン(成分G)と混合し、透明溶液を得た。次いで、30℃まで冷却し、0.743gのDesmodur(登録商標)XP 2410(成分A)を添加し、再び混合した。最後に、0.0140gのFomrez(登録商標)UL 28(成分F)を添加し、再び短く混合した。続いて、得られた液状物質をガラス板上に注ぎ、それを、スペーサーによって20μmの距離に保った第2のガラス板で覆った。この試験片を室温で放置し、16時間にわたって硬化させた。最大Δn:0.0196。
7.711gのポリオール3(成分B)を、3.75gのウレタンアクリレート1(成分C)、0.15gのCGI 909および0.015gのニューメチレンブルー(共成分E)と60℃で、並びに0.525gのN−エチルピロリドン(成分G)と混合し、透明溶液を得た。次いで、30℃まで冷却し、2.823gのDesmodur(登録商標)XP 2599(成分A)を添加し、再び混合した。最後に、0.0389gのFomrez(登録商標)UL 28(成分F)を添加し、再び短く混合した。続いて、得られた液状物質をガラス板上に注ぎ、それを、スペーサーによって20μmの距離に保った第2のガラス板で覆った。この試験片を室温で放置し、16時間にわたって硬化させた。最大Δn:0.0125。
8.827gのポリオール3(成分B)を、4.5gのウレタンアクリレート1(成分C)、0.15gのCGI 909および0.015gのニューメチレンブルー(共成分E)と60℃で、並びに0.525gのN−エチルピロリドン(成分G)と混合し、透明溶液を得た。次いで、30℃まで冷却し、0.958gのDesmodur(登録商標)XP 2580(成分A)を添加し、再び混合した。最後に、0.0255gのFomrez(登録商標)UL 28(成分F)を添加し、再び短く混合した。続いて、得られた液状物質をガラス板上に注ぎ、それを、スペーサーによって20μmの距離に保った第2のガラス板で覆った。この試験片を室温で放置し、16時間にわたって硬化させた。最大Δn:0.0206。
9.533gのポリオール4(成分B)を、3.75gのウレタンアクリレート1(成分C)、0.15gのCGI 909および0.015gのニューメチレンブルー(共成分E)と60℃で、並びに0.525gのN−エチルピロリドン(成分G)と混合し、透明溶液を得た。次いで、30℃まで冷却し、1.001gのDesmodur(登録商標)XP 2580(成分A)を添加し、再び混合した。最後に、0.0342gのFomrez(登録商標)UL 28(成分F)を添加し、再び短く混合した。続いて、得られた液状物質をガラス板上に注ぎ、それを、スペーサーによって20μmの距離に保った第2のガラス板で覆った。この試験片を室温で放置し、16時間にわたって硬化させた。最大Δn:0.0182。
9.611gのポリオール5(成分B)を、3.75gのウレタンアクリレート1(成分C)、0.15gのCGI 909および0.015gのニューメチレンブルー(共成分E)と60℃で、並びに0.525gのN−エチルピロリドン(成分G)と混合し、透明溶液を得た。次いで、30℃まで冷却し、0.924gのDesmodur(登録商標)XP 2580(成分A)を添加し、再び混合した。最後に、0.0300gのFomrez(登録商標)UL 28(成分F)を添加し、再び短く混合した。続いて、得られた液状物質をガラス板上に注ぎ、それを、スペーサーによって20μmの距離に保った第2のガラス板で覆った。この試験片を室温で放置し、16時間にわたって硬化させた。最大Δn:0.0185。
S=シャッター
SF=空間フィルター
CL=コリメーターレンズ
λ/2=λ/2プレート
PBS=偏光感受型ビームスプリッター
D=検出器
I=虹彩絞り
α=21.8°およびβ=41.8°は、試料(媒体)の外側で測定したコヒーレント光線の入射角である。
Claims (13)
- A)ポリイソシアネート成分;
B)1000g/mol超の数平均分子量を有するY(Xi−H)n型:
[ここで、Xiは式(I):
-CH2-CH(R)-O- (I)
で示されるオキシアルキレン単位であり、
iは1〜10の整数であり、
nは2〜8の整数であり、
Rは、水素、アルキルまたはアリール基であり、前記アルキルまたはアリール基は、ヘテロ原子によって任意に置換または中断されていてよく、
Yは基本開始剤であり、セグメントXiおよびYの総量に基づいたセグメントXiの割合は少なくとも50重量%を占める。]
のヒドロキシ官能性マルチブロックコポリマーB1)を含んでなる、イソシアネート反応性成分;
C)重合を介してエチレン性不飽和化合物と化学線の作用下で反応する基を含有するNCO基不含有化合物;
D)ラジカル安定剤;
E)光開始剤;
F)任意に触媒;および
G)任意に助剤および添加剤
を含んでなるポリウレタン組成物。 - 成分A)がHDI、TMDIおよび/またはTINに基づいたポリイソシアネートおよび/またはプレポリマーを含んでなる、請求項1に記載のポリウレタン組成物。
- 成分A)が、イソシアヌレート構造および/またはイミノオキサジアジンジオン構造を有するHDI系ポリイソシアネート、或いは2〜5のNCO官能価を有し、第一級NCO基しか含有しないプレポリマーを含んでなる、請求項1に記載のポリウレタン組成物。
- 成分A)が0.5重量%未満の遊離単量体イソシアネート残留含量を有する、請求項1に記載のポリウレタン組成物。
- 少なくとも1つのセグメントXiが、プロピレンオキシドベースホモポリマーであるか、或いはオキシエチレン、オキシプロピレンおよびオキシブチレン単位全ての総量に基づいた前記オキシプロピレン単位の割合が少なくとも20重量%を占める、オキシエチレン、オキシプロピレンおよび/またはオキシブチレン単位を含有するランダムコポリマーまたはブロックコポリマーである、請求項1に記載のポリウレタン組成物。
- 前記開始剤セグメントYが、250g/mol超〜2100g/mol未満の数平均モル質量を有する二官能性の、脂肪族ポリカーボネートポリオール、ポリ(ε−カプロラクトン)またはテトラヒドロフラン重合体に基づく、請求項1に記載のポリウレタン組成物。
- 前記マルチブロックコポリマーB1)が1200〜12000g/molの数平均分子量を有する、請求項1に記載のポリウレタン組成物。
- 前記した成分C)の化合物が1.55超の屈折率nD 20を有する、請求項1に記載のポリウレタン組成物。
- 成分C)が、芳香族イソシアネートと2−ヒドロキシエチルアクリレート、ヒドロキシプロピルアクリレート、4−ヒドロキシブチルアクリレート、ポリエチレンオキシドモノ(メタ)アクリレート、ポリプロピレンオキシドモノ(メタ)アクリレート、ポリアルキレンオキシドモノ(メタ)アクリレートおよび/またはポリ(ε−カプロラクトン)モノ(メタ)アクリレートとに基づいたウレタンアクリレートおよび/またはウレタンメタクリレートを含んでなる、請求項1に記載のポリウレタン組成物。
- (1)請求項1に記載のポリウレタン組成物を基材にまたは型の中に適用する工程、および(2)前記ポリウレタン組成物を硬化させる工程を含む、映像ホログラム記録用媒体の製造方法。
- 請求項10に記載の方法によって製造された映像ホログラム記録用媒体。
- 請求項11に記載の媒体を含む光学素子または光学像。
- 請求項12に記載の媒体を感光させることを含む、ホログラムの記録方法。
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CN101712744A (zh) | 2010-05-26 |
TWI466947B (zh) | 2015-01-01 |
EP2172503A1 (de) | 2010-04-07 |
SG160311A1 (en) | 2010-04-29 |
RU2009136175A (ru) | 2011-04-10 |
CN101712744B (zh) | 2013-02-13 |
CA2680963A1 (en) | 2010-04-01 |
IL200997A0 (en) | 2010-06-30 |
ATE517137T1 (de) | 2011-08-15 |
US8361678B2 (en) | 2013-01-29 |
RU2510666C2 (ru) | 2014-04-10 |
TW201026781A (en) | 2010-07-16 |
KR101634385B1 (ko) | 2016-06-28 |
EP2172503B1 (de) | 2011-07-20 |
US20100086861A1 (en) | 2010-04-08 |
KR20100037562A (ko) | 2010-04-09 |
JP5535564B2 (ja) | 2014-07-02 |
BRPI0905602A2 (pt) | 2011-03-29 |
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