JP2018505927A - 水分に安定なホログラフィック媒体 - Google Patents
水分に安定なホログラフィック媒体 Download PDFInfo
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- JP2018505927A JP2018505927A JP2017532091A JP2017532091A JP2018505927A JP 2018505927 A JP2018505927 A JP 2018505927A JP 2017532091 A JP2017532091 A JP 2017532091A JP 2017532091 A JP2017532091 A JP 2017532091A JP 2018505927 A JP2018505927 A JP 2018505927A
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- Prior art keywords
- group
- substituted
- phenyl
- unsubstituted
- formula
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims abstract description 59
- 239000000178 monomer Substances 0.000 claims abstract description 24
- 230000003287 optical effect Effects 0.000 claims abstract description 22
- -1 phenylthiyl Chemical group 0.000 claims description 108
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 229920000642 polymer Polymers 0.000 claims description 16
- 239000011159 matrix material Substances 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 125000001931 aliphatic group Chemical group 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 230000005855 radiation Effects 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 8
- 239000004814 polyurethane Substances 0.000 claims description 8
- 229920002635 polyurethane Polymers 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- VUUAEBBAUMJPRE-UHFFFAOYSA-N ethyl n-fluorocarbamate Chemical compound CCOC(=O)NF VUUAEBBAUMJPRE-UHFFFAOYSA-N 0.000 claims description 5
- 235000010290 biphenyl Nutrition 0.000 claims description 4
- 239000004305 biphenyl Substances 0.000 claims description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 4
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 2
- WYKHSBAVLOPISI-UHFFFAOYSA-N 2-phenyl-1,3-thiazole Chemical compound C1=CSC(C=2C=CC=CC=2)=N1 WYKHSBAVLOPISI-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 49
- 239000000975 dye Substances 0.000 description 34
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 21
- 239000000047 product Substances 0.000 description 20
- 239000012948 isocyanate Substances 0.000 description 17
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 description 16
- 239000005056 polyisocyanate Substances 0.000 description 16
- 229920001228 polyisocyanate Polymers 0.000 description 16
- 229920005862 polyol Polymers 0.000 description 16
- 150000003077 polyols Chemical class 0.000 description 16
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 15
- 150000002513 isocyanates Chemical class 0.000 description 14
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 12
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 11
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 11
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 10
- 239000012975 dibutyltin dilaurate Substances 0.000 description 10
- 239000011521 glass Substances 0.000 description 10
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical class O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 10
- 150000001412 amines Chemical class 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 9
- 125000005442 diisocyanate group Chemical group 0.000 description 9
- 239000004417 polycarbonate Substances 0.000 description 9
- 229920000515 polycarbonate Polymers 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 230000005540 biological transmission Effects 0.000 description 8
- 125000005842 heteroatom Chemical group 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 229920000728 polyester Polymers 0.000 description 8
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 7
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 7
- 239000004721 Polyphenylene oxide Substances 0.000 description 7
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 7
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 7
- 125000002091 cationic group Chemical group 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 229920005906 polyester polyol Polymers 0.000 description 7
- 229920000570 polyether Polymers 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 7
- BKJABLMNBSVKCV-UHFFFAOYSA-N 1-isocyanato-3-methylsulfanylbenzene Chemical compound CSC1=CC=CC(N=C=O)=C1 BKJABLMNBSVKCV-UHFFFAOYSA-N 0.000 description 6
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 150000001450 anions Chemical class 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 150000002009 diols Chemical class 0.000 description 6
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 6
- 229920000139 polyethylene terephthalate Polymers 0.000 description 6
- 239000005020 polyethylene terephthalate Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- SHXRQLOTALWECC-UHFFFAOYSA-N 1-isocyanato-2-(3-phenylsulfanylphenyl)sulfanylbenzene Chemical compound N(=C=O)C1=C(C=CC=C1)SC1=CC(=CC=C1)SC1=CC=CC=C1 SHXRQLOTALWECC-UHFFFAOYSA-N 0.000 description 5
- 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 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- 239000007983 Tris buffer Substances 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 239000002131 composite material Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate group Chemical group C(C(=C)C)(=O)[O-] CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 5
- 150000002894 organic compounds Chemical class 0.000 description 5
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000003381 stabilizer Substances 0.000 description 5
- 150000005846 sugar alcohols Polymers 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- PJMDLNIAGSYXLA-UHFFFAOYSA-N 6-iminooxadiazine-4,5-dione Chemical group N=C1ON=NC(=O)C1=O PJMDLNIAGSYXLA-UHFFFAOYSA-N 0.000 description 4
- 239000004952 Polyamide Substances 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 239000001001 arylmethane dye Substances 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 4
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 4
- 229920002647 polyamide Polymers 0.000 description 4
- 239000004926 polymethyl methacrylate Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000013112 stability test Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 description 4
- 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 3
- IHHUGFJSEJSCGE-UHFFFAOYSA-N 1-isocyanato-2-phenylbenzene Chemical compound O=C=NC1=CC=CC=C1C1=CC=CC=C1 IHHUGFJSEJSCGE-UHFFFAOYSA-N 0.000 description 3
- OBIGPOGFLBZPFB-UHFFFAOYSA-N 1-isocyanato-2-phenylsulfanylbenzene Chemical compound O=C=NC1=CC=CC=C1SC1=CC=CC=C1 OBIGPOGFLBZPFB-UHFFFAOYSA-N 0.000 description 3
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 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 3
- GWZMWHWAWHPNHN-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate Chemical compound CC(O)COC(=O)C=C GWZMWHWAWHPNHN-UHFFFAOYSA-N 0.000 description 3
- MKNYZXHUCMYOLD-UHFFFAOYSA-N 2-isocyanato-3-phenylthiophene Chemical compound S1C=CC(C=2C=CC=CC=2)=C1N=C=O MKNYZXHUCMYOLD-UHFFFAOYSA-N 0.000 description 3
- TWBPWBPGNQWFSJ-UHFFFAOYSA-N 2-phenylaniline Chemical group NC1=CC=CC=C1C1=CC=CC=C1 TWBPWBPGNQWFSJ-UHFFFAOYSA-N 0.000 description 3
- FZQMJOOSLXFQSU-UHFFFAOYSA-N 3-[3,5-bis[3-(dimethylamino)propyl]-1,3,5-triazinan-1-yl]-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCN1CN(CCCN(C)C)CN(CCCN(C)C)C1 FZQMJOOSLXFQSU-UHFFFAOYSA-N 0.000 description 3
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 229920002284 Cellulose triacetate Polymers 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- 239000004433 Thermoplastic polyurethane Substances 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 150000001414 amino alcohols Chemical class 0.000 description 3
- 229920001400 block copolymer Polymers 0.000 description 3
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- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
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- 229910052731 fluorine Inorganic materials 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 150000002596 lactones Chemical class 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
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- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
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- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 3
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 3
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- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
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- KGLSETWPYVUTQX-UHFFFAOYSA-N tris(4-isocyanatophenoxy)-sulfanylidene-$l^{5}-phosphane Chemical compound C1=CC(N=C=O)=CC=C1OP(=S)(OC=1C=CC(=CC=1)N=C=O)OC1=CC=C(N=C=O)C=C1 KGLSETWPYVUTQX-UHFFFAOYSA-N 0.000 description 3
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- MXTHSRLPPKBDCB-MBTXQDIMSA-N (3s,5s,10s,13r,14s,17r)-3-[[(3ar,6r)-4-methyl-2-phenyl-4,6,7,7a-tetrahydro-3ah-[1,3]dioxolo[4,5-c]pyran-6-yl]oxy]-5,14-dihydroxy-13-methyl-17-(5-oxo-2h-furan-3-yl)-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthrene-10-carbaldehyde Chemical compound C([C@@H](OC([C@H]1O2)C)O[C@@H]3C[C@@]4(O)CCC5[C@@]6(O)CC[C@@H]([C@@]6(C)CCC5[C@@]4(C=O)CC3)C=3COC(=O)C=3)C1OC2C1=CC=CC=C1 MXTHSRLPPKBDCB-MBTXQDIMSA-N 0.000 description 2
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 description 2
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- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
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- 229960000907 methylthioninium chloride Drugs 0.000 description 1
- JQZWHMOVSQRYRN-UHFFFAOYSA-M n-(2-chloroethyl)-n-ethyl-3-methyl-4-[2-(1,3,3-trimethylindol-1-ium-2-yl)ethenyl]aniline;chloride Chemical compound [Cl-].CC1=CC(N(CCCl)CC)=CC=C1C=CC1=[N+](C)C2=CC=CC=C2C1(C)C JQZWHMOVSQRYRN-UHFFFAOYSA-M 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- CXOYJPWMGYDJNW-UHFFFAOYSA-N naphthalen-2-yl 2-methylprop-2-enoate Chemical compound C1=CC=CC2=CC(OC(=O)C(=C)C)=CC=C21 CXOYJPWMGYDJNW-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 229940065472 octyl acrylate Drugs 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- HSXUHWZMNJHFRV-QIKYXUGXSA-L orange G Chemical compound [Na+].[Na+].OC1=CC=C2C=C(S([O-])(=O)=O)C=C(S([O-])(=O)=O)C2=C1\N=N\C1=CC=CC=C1 HSXUHWZMNJHFRV-QIKYXUGXSA-L 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- QIWKUEJZZCOPFV-UHFFFAOYSA-N phenyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=CC=C1 QIWKUEJZZCOPFV-UHFFFAOYSA-N 0.000 description 1
- WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-UHFFFAOYSA-N 0.000 description 1
- 229940067157 phenylhydrazine Drugs 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 229920001485 poly(butyl acrylate) polymer Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920000909 polytetrahydrofuran Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229940075065 polyvinyl acetate Drugs 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 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
- 238000000197 pyrolysis Methods 0.000 description 1
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical compound C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000004044 response Effects 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
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
- VLDHWMAJBNWALQ-UHFFFAOYSA-N sodium;3h-1,3-benzothiazole-2-thione Chemical compound [Na+].C1=CC=C2SC(S)=NC2=C1 VLDHWMAJBNWALQ-UHFFFAOYSA-N 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical compound [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 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
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000005628 tolylene group Chemical group 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 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
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 101150046896 trm1 gene Proteins 0.000 description 1
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 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
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical compound [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
- 239000001018 xanthene dye Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
- IFNXAMCERSVZCV-UHFFFAOYSA-L zinc;2-ethylhexanoate Chemical compound [Zn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O IFNXAMCERSVZCV-UHFFFAOYSA-L 0.000 description 1
- 150000007934 α,β-unsaturated carboxylic acids Chemical class 0.000 description 1
Images
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/40—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino groups bound to carbon atoms of at least one six-membered aromatic ring and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/26—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
- C07C271/28—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring to a carbon atom of a non-condensed six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/26—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
- C07C323/43—Y being a hetero atom
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- 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
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- 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
- G03F7/0046—Photosensitive materials with perfluoro compounds, e.g. for dry lithography
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- 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
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- 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
- G03F7/035—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polyurethanes
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- 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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- G03H1/024—Hologram nature or properties
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- G03H—HOLOGRAPHIC PROCESSES OR APPARATUS
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- G03H2260/12—Photopolymer
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- G03H—HOLOGRAPHIC PROCESSES OR APPARATUS
- G03H2260/00—Recording materials or recording processes
- G03H2260/30—Details of photosensitive recording material not otherwise provided for
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Holo Graphy (AREA)
- Polyurethanes Or Polyureas (AREA)
- Polymerisation Methods In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Diffracting Gratings Or Hologram Optical Elements (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
R3は、独立して、置換または非置換フェニル、置換または非置換フェニルチイル、分岐または非分岐アルキル、分岐または非分岐アルキルチイル、ハロゲンの群から選択される基であり、ここで、R3基の少なくとも1つが、置換または非置換フェニル、置換または非置換フェニルチイルの群から選択される基であり、
n=1〜5である)の芳香族基であるか、
Arは、式(III):
R3は、独立して、置換または非置換フェニル、置換または非置換フェニルチイル、分岐または分岐枝アルキル、分岐または非分岐アルキルチイル、ハロゲンの群から選択される基であり、ここで、R3基の少なくとも1つが、置換または非置換フェニル、置換または非置換フェニルチイルの群から選択される基であり、
o=1〜3、
p=1〜4である)の芳香族基である)の化合物であって、上記式(I)の化合物はただ1つの放射線硬化性基を有する、化合物によって解決される。
R3’は、独立して、非置換フェニル、置換または非置換フェニルチイル、分岐または非分岐アルキル、分岐または非分岐アルキルチイル、ハロゲンの群から選択される基であり、ここで、R3’基の少なくとも1つが、置換または非置換フェニル、置換または非置換フェニルチイルの群から選択される基であり、
n=1〜5である)の芳香族基であるか、
Arは、式(III):
R3は、独立して、置換または非置換フェニル、置換または非置換フェニルチイル、分岐または非分岐アルキル、分岐または非分岐アルキルチイル、ハロゲンの群から選択される基であり、ここで、R3基の少なくとも1つが、置換または非置換フェニル、置換または非置換フェニルチイルの群から選択される基であり、
o=1〜3、
p=1〜4である)の芳香族基である)の化合物であって、上記式(I’)の化合物はただ1つの放射線硬化性基を有する、化合物によってさらに解決される。
4−イソシアナト−1−ナフチルフェニルスルフィド、4−イソシアナト−5−メチル−1−ナフチルフェニルスルフィド、4−イソシアナト−5−エチル−1−ナフチルフェニルスルフィド、4−イソシアナト−5−プロピル−1−ナフチルフェニルスルフィド、4−イソシアナト−5−ブチル−1−ナフチルフェニルスルフィド、4−イソシアナト−5−オクチル−1−ナフチルフェニルスルフィド、5−フルオロ−4−イソシアナト−1−ナフチルフェニルスルフィド、5−クロロ−4−イソシアナト−1−ナフチルフェニルスルフィド、5−ブロモ−4−イソシアナト−1−ナフチルフェニルスルフィド、5−ヨード−4−イソシアナト−1−ナフチルフェニルスルフィド、4−イソシアナト−5−(メチルスルファニル)−1−(フェニルスルファニル)ナフタレン、4−イソシアナト−5−(エチルスルファニル)−1−(フェニルスルファニル)ナフタレンおよびそれらの位置異性体も好適である。1−イソシアナト−4−フェニルナフタレンおよび4−イソシアナト−1−ナフチルフェニルスルフィドが好ましい。
好適なアンモニウムアルキルアリールボレートは、例えば(Cunninghamら、RadTech’98 North America UV/EB Conference Proceedings, シカゴ, Apr.19−22, 1998)、テトラブチルアンモニウムトリフェニルヘキシルボレート、テトラブチルアンモニウムトリフェニルブチルボレート、テトラブチルアンモニウムトリナフチルヘキシルボレート、テトラブチルアンモニウムトリス(4−tert−ブチル)フェニルブチルボレート、テトラブチルアンモニウムトリス(3−フルオロフェニル)ヘキシルボレートヘキシルボレート([191726−69−9]、CGI 7460、BASF SE、バーゼル、スイスからの製品)、1−メチル−3−オクチルイミダゾリウムジペンチルジフェニルボレートおよびテトラブチルアンモニウムトリス(3−クロロ−4−メチルフェニル)ヘキシルボレート([1147315−11−4]、CGI909、BASF SE、バーゼル、スイスからの製品)である。
本発明を、実施例によって、さらに詳細に説明する。
粘度の決定
Physica MCR 51(Anton Paar製)粘度計を用いて粘度を決定した。この目的のために、サンプルを平衡化し、ボールを懸濁させた(低粘度η<10000mPas:23℃、ボール直径25mm(CP−25)、高粘度η>10000mPas:50°C、ボール直径60mm(CP−60))。約0.5〜1gの生成物をプレート上に置き、ボールが生成物によって完全に濡れるようにボールを落下させた。余分な生成物を拭き取った。装置によって剪断速度(低粘度で約500 1/sおよび高粘度で約100 1/s)を自動的に設定した。それぞれ20回の測定を行い、平均値を求めた。
報告されたNCO値(イソシアネート含有量)をDIN EN ISO 11909に定量化した。
いずれの場合も、CAS番号がわかっている場合、角括弧内に記載する。
ヒドロキシプロピルアクリレート [25584−83−2]−BASF SE、ルートヴィヒスハーフェン、ドイツ
2,6−ジ−tert−ブチル−4−メチルフェノール [128−37−0]−Merck KGaA、ダルムシュタット、ドイツ
2−アミノビフェニル [90−41−5]−Sigma−Aldrich Chemie GmbH、シュタインハイム、ドイツ
2−アミノビフェニルフェニルスルフィド [1134−94−7]−Sigma−Aldrich Chemie GmbH、シュタインハイム、ドイツ
3−(メチルチオ)フェニルイソシアネート [28479−19−8]−Sigma−Aldrich Chemie GmbH、シュタインハイム、ドイツ
1−イソシアナト−3−(メチルスルファニル)ベンゼン [28479−19−8]−Sigma−Aldrich Chemie GmbH、シュタインハイム、ドイツ
Desmodur(登録商標)RFE トリス(p−イソシアナトフェニル)チオホスフェート、酢酸エチル中27%、のBayer MaterialScience AG、レバークーゼン、ドイツからの製品
ジブチル錫ジラウレート [77−58−7]−Sigma−Aldrich Chemie GmbH、シュタインハイム、ドイツ
Fomrez(登録商標)UL 28 Momentive Performance Chemicals、ウィルトン、CT、米国
Borchi(登録商標)Kat 22 [85203−81−2]−OMG Borchers GmbH、ランゲンフェルト、ドイツ
BYK−310 BYK−Chemie GmbH、ヴェーゼル、ドイツ
クロロギ酸フェニル [1885−14−9]−Acros Organics、ヘール、ベルギー
Desmodur(登録商標)N 3900 Bayer MaterialScience AG、レバークーゼン、ドイツ、ヘキサンジイソシアネート系ポリイソシアネート、イミノオキサジアジンジオンの割合が少なくとも30%、NCO含有量が23.5%。
Desmorapid(登録商標)SO [301−10−0]−Rhein Chemie Rheinau GmbH、マンハイム、ドイツ
CGI−909 テトラブチルアンモニウムトリス(3−クロロ−4−メチルフェニル)(ヘキシル)ボレート[1147315−11−4]、BASF SE
トリメチルヘキサメチレンジイソシアネート [28679−16−5]−ABCR GmbH&Co KG、カールスルーエ、ドイツ
1H,1H−7H−パーフルオロヘプタン−1−オール [335−99−9]−ABCR GmbH&Co KG、カールスルーエ、ドイツ
Astrazon Rosa FG 200% [3648−36−0]−DyStar Colours Deutschland GmbH、フランクフルト・アム・マイン、ドイツ
ビス(2−エチルヘキシル)スルホスクシネートナトリウム [45297−26−5]Sigma−Aldrich Chemie GmbH、シュタインハイム、ドイツ
2−フェニルチオフェニルイソシアネートの調製
精密ガラス撹拌機を備えた三口フラスコ内で、窒素下でトルエン4.2kgに2−アミノビフェニルフェニルスルフィド720gを溶解し、撹拌しながら炭酸カリウム519gを加え、混合物を10℃に平衡化させた。次にクロロギ酸フェニル560gを滴下した。生成物を濾過し、減圧下で乾燥させた。これにより、1.15kgのフェニル[2−(フェニルスルファニル)フェニル]カルバメートが結晶沈殿物の形態で得られた。
滴下漏斗、精密ガラス撹拌機および蒸留アタッチメントを備えた三口フラスコに、1500gのDesmodur 2460Mを最初に入れ、140℃に加熱した。次いで、50分以内に、2−アミノビフェニル243.7gを添加し、反応温度を160℃未満に保った。続いて、生成物を高真空下(約0.03mbar)で留去し、透明な液体である2−ビフェニルイソシアネート203.2gを得た。
ジクロロメタン/水(1:1)470gに、Advanced Synthesis&Catalysis(2009)、351(14+15)、2369−2378に記載されているように調製した)2−{[3−(フェニルスルファニル)フェニル]スルファニル}アニリン100gおよびテトラブチルアンモニウムブロマイド0.1gを溶解し、炭酸カリウム49.1gを加えた。10℃で、激しく撹拌した混合物にクロロギ酸フェニル53.1gを滴下した。反応が終了した後、メタノール0.52gを加え、混合物を室温でさらに1時間撹拌した。粗生成物を1Lの水に放出し、各回500mLのジクロロメタンを用いて水相を3回抽出した。有機相を乾燥させ、溶媒を減圧下で留去した。これによりフェニル(2−{[3−(フェニルスルファニル)フェニル]スルファニル}フェニル)カルバメート133gが無色固体として得られた。
凝縮器、精密ガラス撹拌機および窒素ガス導入口を備えた三口フラスコに、2−フェニルチオフェニルイソシアネート16.0gを最初に入れ、反応容器を窒素でパージし、次いで80℃に加熱した。次いで、5mgの2,6−ジ−tert−ブチル−4−メチルフェノールおよび1mgのBochi−Kat 22を添加した。15分間撹拌した後、ヒドロキシプロピルアクリレート9.01gを20分以内に滴下した。混合物を18時間撹拌し、2−({[2−(フェニルスルファニル)フェニル]カルバモイル}オキシ)プロピルアクリレートを、もはやイソシアネートを含まない透明な液体として得た。
凝縮器、精密ガラス撹拌機および空気注入口を備えた三口フラスコに、2−フェニルチオフェニルイソシアネート45.9g、2,6−ジ−tert−ブチル−4−メチルフェノール13.5mgおよびジブチル錫ジラウレート33.8gを最初に入れ、60℃に加熱した。20分間撹拌した後、ヒドロキシエチルアクリレート21.6gを10分以内に滴下した。混合物を19時間撹拌し、ジブチル錫ジラウレートをさらに30mg加えた。さらに32時間後、ヒドロキシアルキルアクリレート1.08gをさらに添加し、さらに5時間撹拌した後、もはやイソシアネートを含まない2−({[2−(フェニルスルファニル)フェニル]カルバモイル}オキシ)エチルアクリレートを透明な液体として得た。
凝縮器、精密ガラス撹拌機および空気注入口を備えた三口フラスコに、ビフェニル2−イソシアネート7.8gおよび2,6−ジ−tert−ブチル−4−メチルフェノール2.6mgを最初に入れ、次いで60℃に加熱した。次いで、空気を徐々に導入しながら、ヒドロキシプロピルアクリレート5.2gを30分以内に滴下した。1.5時間後、ジブチル錫ジラウレート6.5mgを加えた。混合物を46時間撹拌し、2−[(ビフェニル−2−イルカルバモイル)オキシ]プロピルアクリレートを、もはやイソシアネートを含まない透明な液体として得た。
凝縮器、精密ガラス撹拌機および空気注入口を備えた三口フラスコに、ビフェニル2−イソシアネート7.8gおよび2,6−ジ−tert−ブチル−4−メチルフェノール2.4mgを最初に入れ、次いで60℃に加熱した。次に、空気を徐々に導入しながら2−ヒドロキシエチルアクリレート4.3gを30分以内に滴下した。1.5時間後、ジブチル錫ジラウレート6.1mgを添加した。混合物を70時間撹拌し、2−[(ビフェニル−2−イルカルバモイル)オキシ]エチルアクリレートを、もはやイソシアネートを含まない透明な液体として得て、徐々に結晶化させて110〜120℃の融解範囲を有する固体を得た。
100mLの丸底フラスコに、2,6−ジ−tert−ブチル−4−メチルフェノール0.01g、ジブチル錫ジラウレート0.01gおよび1−イソシアナト−2−{[3−(フェニルスルファニル)フェニル]スルファニル}ベンゼン7.50gの30mLの酢酸エチル溶液を最初に入れ、60℃に加熱した。続いて2−ヒドロキシエチルアクリレート2.50gを滴下し、イソシアネート含有量が0.1%を下回るまで混合物を60℃に保った。これに続いて冷却し、減圧下で酢酸エチルを完全に除去した。生成物を、部分的に結晶性の固体として得た。
100mLの丸底フラスコに、2,6−ジ−tert−ブチル−4−メチルフェノール0.01g、ジブチル錫ジラウレート0.01gおよび1−イソシアナト−2−{[3−(フェニルスルファニル)フェニル]スルファニル}ベンゼン7.30gの30mLの酢酸エチル溶液を最初に入れ、60℃に加熱した。続いてヒドロキシプロピルアクリレート2.70gを滴下し、イソシアネート含有量が0.1%を下回るまで混合物を60℃に保った。これに続いて冷却し、減圧下で酢酸エチルを完全に除去した。生成物を、部分的に結晶性の固体として得た。
100mLの丸底フラスコに、2,6−ジ−tert−ブチル−4−メチルフェノール0.02g、ジブチル錫ジラウレート0.01g、3−(メチルチオ)フェニルイソシアネート11.7gを最初に入れ、混合物を60℃に加熱した。続いて、2−ヒドロキシエチルアクリレート8.2gを滴下し、イソシアネート含有量が0.1%を下回るまで混合物を60°Cに保った。これに続いて冷却を行った。生成物を無色液体として得た。
500mLの丸底フラスコに、2,6−ジ−tert−ブチル−4−メチルフェノール0.1g、ジブチル錫ジラウレート0.05gおよびトリス(p−イソシアナトフェニル)チオホスフェートの27%酢酸エチル溶液213.1g(Desmodur(登録商標)RFE、Bayer MaterialScience AG、レバークーゼン、ドイツからの製品)を最初に入れ、60°Cに加熱した。続いて、2−ヒドロキシエチルアクリレート42.4gを滴下し、イソシアネート含有量が0.1%を下回るまで混合物を60℃に保った。これに続いて冷却し、減圧下で酢酸エチルを完全に除去した。生成物を、部分的に結晶性の固体として得た。
1Lのフラスコに、Desmorapid(登録商標)SO0.037g、ε−カプロラクトン374.8gおよび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374.8gを最初に入れ、これらを120°Cに加熱し、固体含量(不揮発成分の割合)が99.5重量%以上になるまでこの温度で維持した。続いて、混合物を冷却し、生成物をワックス状固体として得た。
無水ビス(2−エチルヘキシル)スルホスクシネートナトリウム5.84gを酢酸エチル75mLに溶解した。水50mLに溶解した染料Astrazon Rosa FG200%(14.5g)を添加した。水相を除去し、50°Cの新鮮な水50mLで有機相を3回撹拌し、最後は室温で水相をその都度除去した。水相を除去した後、溶媒を減圧留去し、3H−インドリウム、2−[2−[4−[(2−クロロエチル)メチルアミノ]フェニル]エテニル]−1,3,3−トリメチル−1,4−ビス(2−エチルヘキシル)スルホスクシネート[153952−28−4]8.6gを高粘度の油として得た。
6Lの丸底フラスコに、Desmorapid Z 0.50gおよびトリメチルヘキサメチレンジイソシアネート1200gを最初に入れ、混合物を80℃に加熱した。その後、1H,1H,7H−パーフルオロヘプタン−1−オール3798gを滴下し、イソシアネート含有量が0.1%を下回るまで混合物を80℃に保った。これに続いて冷却を行った。生成物を無色油状物として得た。
上記のポリオール成分7.90gを融解し、特定の書込モノマー(書込モノマー1〜6および比較例A)7.65g、上記のウレタンアクリレート1 2.57g、上記のフッ素化ウレタン5.10g、CGI909 0.91g、染料1 0.232g、BYK310 0.230g、Fomrez UL28 0.128gおよび酢酸エチル3.789gと混合して透明な溶液を得た。これに続いてDesmodur(登録商標)N 3900 1.50gを添加し、再び混合した。
「本発明のホログラフィック媒体および本発明のものでないホログラフィック媒体の製造」の項に記載のとおり製造された媒体を、図4による測定装置を使用して以下のようにホログラフィック特性について試験した。
サンプルをオーブン内で100℃で2日間保存し、2分以内の間冷却し、Tmin(1)を決定した。続いて、サンプルを約20℃および40%〜50%の相対湿度で7日間保存し、Tmin(2)を決定した。最後に、2つの測定値ΔTmin(1)のピーク波長の差を計算した。
サンプルを空気の相対湿度60°C/95%で2日間保存し、2分以内の間冷却し、Tmin(3)を決定した。続いて、サンプルを約20℃および40%〜50%の相対湿度で7日間保存し、Tmin(4)を決定した。最後に、2つの測定値ΔTmin(2)のピーク波長の差を計算した。
Claims (15)
- マトリックスポリマー、書込モノマーおよび光開始剤を含むフォトポリマーであって、前記書込モノマーは、式(I):
R1は1〜8個の炭素原子を有する脂肪族ヒドロカルビル基であり、
R2は水素またはメチルであり、
Arは、式(II):
R3は、独立して、置換または非置換フェニル、置換または非置換フェニルチイル、分岐または非分岐アルキル、分岐または非分岐アルキルチイル、ハロゲンの群から選択される基であり、ここで、前記R3の基の少なくとも1つが、置換または非置換フェニル、置換または非置換フェニルチイルの群から選択される基であり、
n=1〜5である)
の芳香族基であるか、
Arは、式(III):
o=1〜3、
p=1〜4である)
の芳香族基である)
の化合物を含み、
前記式(I)の化合物はただ1つの放射線硬化性基を有する、フォトポリマー。 - 前記R3の基の少なくとも1つが、フェニル、フェニルチイル、フェニルチイルフェニルチイル、アルキルフェニル、アルキルフェニルチイル、ビフェニルの群から選択されることを特徴とする請求項1に記載のフォトポリマー。
- Arが式(II)の基であることを特徴とする請求項1および2のいずれかに記載のフォトポリマー。
- o=1であることを特徴とする請求項1〜3のいずれかに記載のフォトポリマー。
- R1が、−CH2−CH2−、−CH2−CH2−CH2−、−CH2−CHCH3−、−CH2−CH2−CH2−CH2−の群から選択される基であることを特徴とする請求項1〜4のいずれかに記載のフォトポリマー。
- 前記マトリックスポリマーが、架橋マトリックスポリマー、好ましくは三次元架橋マトリックスポリマーであり、最も好ましくは三次元架橋ポリウレタンであることを特徴とする請求項1〜5のいずれかに記載のフォトポリマー。
- モノマーフルオロウレタンを含むことを特徴とする請求項1〜6のいずれかに記載のフォトポリマー。
- 請求項1〜8のいずれかに記載のフォトポリマーを含むホログラフィック媒体。
- 好ましくは0.3μm〜500μmのフィルム厚さ、さらに好ましくは0.5μm〜200μmのフィルム厚さ、さらにいっそう好ましくは1μm〜100μmのフィルム厚さを有するフィルムであることを特徴とする請求項8に記載のホログラフィック媒体。
- 前記ホログラフィック媒体に少なくとも1つのホログラムが記録されたことを特徴とする請求項8および9のいずれかに記載のホログラフィック媒体。
- 請求項8〜10のいずれかに記載のホログラフィック媒体を含む光学ディスプレイ。
- 請求項8〜10のいずれかに記載のホログラフィック媒体を含むセキュリティ文書。
- 請求項8〜10のいずれかに記載のホログラフィック媒体を含むホログラフィック光学素子。
- 式(I’):
R1は1〜8個の炭素原子を有する脂肪族ヒドロカルビル基であり、
R2は水素またはメチルであり、
Arは、式(II’):
R3’は、独立して、非置換フェニル、置換または非置換フェニルチイル、分岐または非分岐アルキル、分岐または非分岐アルキルチイル、ハロゲンの群から選択される基であり、ここで、前記R3’の基の少なくとも1つが、置換または非置換フェニル、置換または非置換フェニルチイルの群から選択される基であり、
n=1〜5である)
の芳香族基であるか、
Arは、式(III):
R3は、独立して、置換または非置換フェニル、置換または非置換フェニルチイル、分岐または非分岐アルキル、分岐または非分岐アルキルチイル、ハロゲンの群から選択される基であり、ここで、前記R3の基の少なくとも1つが、置換または非置換フェニル、置換または非置換フェニルチイルの群から選択される基であり、
o=1〜3、
p=1〜4である)
の芳香族基である)
の化合物であって、
前記式(I’)の化合物はただ1つの放射線硬化性基を有する、化合物。 - フォトポリマー、ホログラフィック媒体および/またはホログラフィック光学素子中の書込モノマーとしての式(I)の化合物の使用。
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