JP4645925B2 - （メタ）アクリル酸エステル誘導体 - Google Patents
（メタ）アクリル酸エステル誘導体 Download PDFInfo
- Publication number
- JP4645925B2 JP4645925B2 JP2010523636A JP2010523636A JP4645925B2 JP 4645925 B2 JP4645925 B2 JP 4645925B2 JP 2010523636 A JP2010523636 A JP 2010523636A JP 2010523636 A JP2010523636 A JP 2010523636A JP 4645925 B2 JP4645925 B2 JP 4645925B2
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- JP
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- Prior art keywords
- acrylate
- meth
- acrylic acid
- group
- acid ester
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 title claims description 41
- 239000000203 mixture Substances 0.000 claims description 15
- 230000003287 optical effect Effects 0.000 claims description 11
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 81
- -1 acrylate ester Chemical class 0.000 description 80
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- 239000000047 product Substances 0.000 description 26
- 239000000126 substance Substances 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 23
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 23
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 239000011342 resin composition Substances 0.000 description 16
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 14
- 239000003822 epoxy resin Substances 0.000 description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 14
- 229920000647 polyepoxide Polymers 0.000 description 14
- 125000001424 substituent group Chemical group 0.000 description 13
- 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 12
- 150000001875 compounds Chemical class 0.000 description 12
- 239000010410 layer Substances 0.000 description 12
- 238000005160 1H NMR spectroscopy Methods 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 11
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000178 monomer Substances 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000004593 Epoxy Substances 0.000 description 8
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 8
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 8
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 8
- 229920005862 polyol Polymers 0.000 description 8
- 150000003077 polyols Chemical class 0.000 description 8
- 238000000926 separation method Methods 0.000 description 8
- CMQZETQFZHIYJG-UHFFFAOYSA-N 2-(n-phenylanilino)ethanol Chemical compound C=1C=CC=CC=1N(CCO)C1=CC=CC=C1 CMQZETQFZHIYJG-UHFFFAOYSA-N 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 239000003085 diluting agent Substances 0.000 description 6
- 239000005056 polyisocyanate Substances 0.000 description 6
- 229920001228 polyisocyanate Polymers 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- BAPJBEWLBFYGME-UHFFFAOYSA-N acrylic acid methyl ester Natural products COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 5
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- OQLUVXFTYJYDMT-UHFFFAOYSA-N 3,3-diphenylpropyl prop-2-enoate Chemical compound C(C=C)(=O)OCCC(C1=CC=CC=C1)C1=CC=CC=C1 OQLUVXFTYJYDMT-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 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
- 239000007795 chemical reaction product Substances 0.000 description 4
- 238000010894 electron beam technology Methods 0.000 description 4
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000007493 shaping process Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 238000005809 transesterification reaction Methods 0.000 description 4
- IRONUJWKTLBGAD-UHFFFAOYSA-N (2-benzylphenyl)methyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=CC=C1CC1=CC=CC=C1 IRONUJWKTLBGAD-UHFFFAOYSA-N 0.000 description 3
- LAZXUBKSQQRBNY-UHFFFAOYSA-N (2-phenoxyphenyl)methyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=CC=C1OC1=CC=CC=C1 LAZXUBKSQQRBNY-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
- VAZQKPWSBFZARZ-UHFFFAOYSA-N 2-(2-phenylphenoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC1=CC=CC=C1C1=CC=CC=C1 VAZQKPWSBFZARZ-UHFFFAOYSA-N 0.000 description 3
- RHOOUTWPJJQGSK-UHFFFAOYSA-N 2-phenylsulfanylethyl prop-2-enoate Chemical compound C=CC(=O)OCCSC1=CC=CC=C1 RHOOUTWPJJQGSK-UHFFFAOYSA-N 0.000 description 3
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 239000001110 calcium chloride Substances 0.000 description 3
- 229910001628 calcium chloride Inorganic materials 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000004973 liquid crystal related substance Substances 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 3
- 229950000688 phenothiazine Drugs 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 2
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 2
- GBGXVCNOKWAMIP-UHFFFAOYSA-N 1,2-diphenylethanol Chemical compound C=1C=CC=CC=1C(O)CC1=CC=CC=C1 GBGXVCNOKWAMIP-UHFFFAOYSA-N 0.000 description 2
- DUCKEMWTXUYAEU-UHFFFAOYSA-N 1,2-diphenylethyl prop-2-enoate Chemical compound C(C=C)(=O)OC(CC1=CC=CC=C1)C1=CC=CC=C1 DUCKEMWTXUYAEU-UHFFFAOYSA-N 0.000 description 2
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 2
- JWYVGKFDLWWQJX-UHFFFAOYSA-N 1-ethenylazepan-2-one Chemical compound C=CN1CCCCCC1=O JWYVGKFDLWWQJX-UHFFFAOYSA-N 0.000 description 2
- XLPJNCYCZORXHG-UHFFFAOYSA-N 1-morpholin-4-ylprop-2-en-1-one Chemical compound C=CC(=O)N1CCOCC1 XLPJNCYCZORXHG-UHFFFAOYSA-N 0.000 description 2
- HLDSNTBYNBFQQM-UHFFFAOYSA-N 2,2-diphenylethyl prop-2-enoate Chemical compound C=1C=CC=CC=1C(COC(=O)C=C)C1=CC=CC=C1 HLDSNTBYNBFQQM-UHFFFAOYSA-N 0.000 description 2
- FIOCEWASVZHBTK-UHFFFAOYSA-N 2-[2-(2-oxo-2-phenylacetyl)oxyethoxy]ethyl 2-oxo-2-phenylacetate Chemical compound C=1C=CC=CC=1C(=O)C(=O)OCCOCCOC(=O)C(=O)C1=CC=CC=C1 FIOCEWASVZHBTK-UHFFFAOYSA-N 0.000 description 2
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 2
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 2
- VNGLVZLEUDIDQH-UHFFFAOYSA-N 4-[2-(4-hydroxyphenyl)propan-2-yl]phenol;2-methyloxirane Chemical compound CC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 VNGLVZLEUDIDQH-UHFFFAOYSA-N 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 0 CCC(C*(CC)N)*C Chemical compound CCC(C*(CC)N)*C 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- FHLPGTXWCFQMIU-UHFFFAOYSA-N [4-[2-(4-prop-2-enoyloxyphenyl)propan-2-yl]phenyl] prop-2-enoate Chemical class C=1C=C(OC(=O)C=C)C=CC=1C(C)(C)C1=CC=C(OC(=O)C=C)C=C1 FHLPGTXWCFQMIU-UHFFFAOYSA-N 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- CHQVQXZFZHACQQ-UHFFFAOYSA-M benzyl(triethyl)azanium;bromide Chemical compound [Br-].CC[N+](CC)(CC)CC1=CC=CC=C1 CHQVQXZFZHACQQ-UHFFFAOYSA-M 0.000 description 2
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 2
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical group C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 2
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical group C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 230000001678 irradiating effect Effects 0.000 description 2
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 239000000113 methacrylic resin Substances 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
- 229920003986 novolac Polymers 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920001610 polycaprolactone Polymers 0.000 description 2
- 239000004632 polycaprolactone Substances 0.000 description 2
- 229920005906 polyester polyol Polymers 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- HVYVMSPIJIWUNA-UHFFFAOYSA-N triphenylstibine Chemical compound C1=CC=CC=C1[Sb](C=1C=CC=CC=1)C1=CC=CC=C1 HVYVMSPIJIWUNA-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 2
- GGWJGWXPTYASHH-UHFFFAOYSA-N (2-benzylphenyl) prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1CC1=CC=CC=C1 GGWJGWXPTYASHH-UHFFFAOYSA-N 0.000 description 1
- GTKWHQWJTVWORA-UHFFFAOYSA-N (2-benzylphenyl)methanol Chemical compound OCC1=CC=CC=C1CC1=CC=CC=C1 GTKWHQWJTVWORA-UHFFFAOYSA-N 0.000 description 1
- FGGRLKWCMJMSKS-UHFFFAOYSA-N (2-phenoxy-2-phenylethyl) prop-2-enoate Chemical compound C=1C=CC=CC=1C(COC(=O)C=C)OC1=CC=CC=C1 FGGRLKWCMJMSKS-UHFFFAOYSA-N 0.000 description 1
- VMZBMTWFHYYOIN-UHFFFAOYSA-N (2-phenoxyphenyl)methanol Chemical compound OCC1=CC=CC=C1OC1=CC=CC=C1 VMZBMTWFHYYOIN-UHFFFAOYSA-N 0.000 description 1
- BKURIUJJNPEQKT-UHFFFAOYSA-N (3-benzylphenyl) prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC(CC=2C=CC=CC=2)=C1 BKURIUJJNPEQKT-UHFFFAOYSA-N 0.000 description 1
- VHOOUJVKRSDRRE-UHFFFAOYSA-N (3-phenoxyphenyl) prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC(OC=2C=CC=CC=2)=C1 VHOOUJVKRSDRRE-UHFFFAOYSA-N 0.000 description 1
- BXSPZNVFEYWSLZ-UHFFFAOYSA-N (3-phenoxyphenyl)methyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 BXSPZNVFEYWSLZ-UHFFFAOYSA-N 0.000 description 1
- GLARBKMIVXLNQX-UHFFFAOYSA-N (4-benzylphenyl)methyl prop-2-enoate Chemical compound C1=CC(COC(=O)C=C)=CC=C1CC1=CC=CC=C1 GLARBKMIVXLNQX-UHFFFAOYSA-N 0.000 description 1
- GFGKESQRIKWOBD-UHFFFAOYSA-N (4-phenoxyphenyl) prop-2-enoate Chemical compound C1=CC(OC(=O)C=C)=CC=C1OC1=CC=CC=C1 GFGKESQRIKWOBD-UHFFFAOYSA-N 0.000 description 1
- UCWHUQORPNJRMB-UHFFFAOYSA-N (4-phenoxyphenyl)methyl prop-2-enoate Chemical compound C1=CC(COC(=O)C=C)=CC=C1OC1=CC=CC=C1 UCWHUQORPNJRMB-UHFFFAOYSA-N 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
- IZVAZAFKVRNZDS-UHFFFAOYSA-N 1-(n-benzylanilino)ethanol Chemical compound C=1C=CC=CC=1N(C(O)C)CC1=CC=CC=C1 IZVAZAFKVRNZDS-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- IZWHBDFVJWKLDL-UHFFFAOYSA-N 2-(2-phenoxyphenoxy)ethanol Chemical compound OCCOC1=CC=CC=C1OC1=CC=CC=C1 IZWHBDFVJWKLDL-UHFFFAOYSA-N 0.000 description 1
- WTTWSMJHJFNCQB-UHFFFAOYSA-N 2-(dibenzylamino)ethanol Chemical compound C=1C=CC=CC=1CN(CCO)CC1=CC=CC=C1 WTTWSMJHJFNCQB-UHFFFAOYSA-N 0.000 description 1
- UGIJCMNGQCUTPI-UHFFFAOYSA-N 2-aminoethyl prop-2-enoate Chemical compound NCCOC(=O)C=C UGIJCMNGQCUTPI-UHFFFAOYSA-N 0.000 description 1
- JSYRPEKHRQJXQK-UHFFFAOYSA-N 2-benzhydryloxyethanol Chemical compound C=1C=CC=CC=1C(OCCO)C1=CC=CC=C1 JSYRPEKHRQJXQK-UHFFFAOYSA-N 0.000 description 1
- LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 description 1
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 1
- OTKLRHWBZHQJOP-UHFFFAOYSA-N 3-aminopropyl prop-2-enoate Chemical compound NCCCOC(=O)C=C OTKLRHWBZHQJOP-UHFFFAOYSA-N 0.000 description 1
- RLDBEKMVLZFHOT-UHFFFAOYSA-N 4,4-diphenylbutyl prop-2-enoate Chemical compound C=1C=CC=CC=1C(CCCOC(=O)C=C)C1=CC=CC=C1 RLDBEKMVLZFHOT-UHFFFAOYSA-N 0.000 description 1
- IEOMKERTJQIKKF-UHFFFAOYSA-N 4-aminobutyl prop-2-enoate Chemical compound NCCCCOC(=O)C=C IEOMKERTJQIKKF-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- KBORYXBZNHGJCA-UHFFFAOYSA-N C(C=C)(=O)OC(C1=CC=CC=C1)CCC1=CC=CC=C1 Chemical compound C(C=C)(=O)OC(C1=CC=CC=C1)CCC1=CC=CC=C1 KBORYXBZNHGJCA-UHFFFAOYSA-N 0.000 description 1
- LXUFJNWBXOWXBM-UHFFFAOYSA-N C(C=C)(=O)OC1=C(C=CC=C1)OC1=CC=CC=C1.C(C=C)(=O)OC1=CC=C(C=C1)CC1=CC=CC=C1 Chemical compound C(C=C)(=O)OC1=C(C=CC=C1)OC1=CC=CC=C1.C(C=C)(=O)OC1=CC=C(C=C1)CC1=CC=CC=C1 LXUFJNWBXOWXBM-UHFFFAOYSA-N 0.000 description 1
- BKSUBTCSGSOPIZ-UHFFFAOYSA-N C(C=C)(=O)OC1=CC(=CC=C1)CCC1=CC=CC=C1 Chemical compound C(C=C)(=O)OC1=CC(=CC=C1)CCC1=CC=CC=C1 BKSUBTCSGSOPIZ-UHFFFAOYSA-N 0.000 description 1
- FFXMWNZCIVHAMH-UHFFFAOYSA-N C(C=C)(=O)OCC1=CC(=CC=C1)CC1=CC=CC=C1 Chemical compound C(C=C)(=O)OCC1=CC(=CC=C1)CC1=CC=CC=C1 FFXMWNZCIVHAMH-UHFFFAOYSA-N 0.000 description 1
- TUFUVIQGTAUBPS-UHFFFAOYSA-N C(C=C)(=O)OCC1=CC(=CC=C1)CCC1=CC=CC=C1 Chemical compound C(C=C)(=O)OCC1=CC(=CC=C1)CCC1=CC=CC=C1 TUFUVIQGTAUBPS-UHFFFAOYSA-N 0.000 description 1
- JHFRYAORIYYDBB-UHFFFAOYSA-N C(C=C)(=O)OCC1=CC=C(C=C1)CCC1=CC=CC=C1 Chemical compound C(C=C)(=O)OCC1=CC=C(C=C1)CCC1=CC=CC=C1 JHFRYAORIYYDBB-UHFFFAOYSA-N 0.000 description 1
- WAGNOINPTXQZLM-UHFFFAOYSA-N C1(=CC=CC=C1)C(N(C)C(C)O)C1=CC=CC=C1 Chemical compound C1(=CC=CC=C1)C(N(C)C(C)O)C1=CC=CC=C1 WAGNOINPTXQZLM-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 238000003848 UV Light-Curing Methods 0.000 description 1
- OPVGPOZNTNYEGU-UHFFFAOYSA-N [2-(2-phenylethyl)phenyl] prop-2-enoate Chemical compound C(C=C)(=O)OC1=C(C=CC=C1)CCC1=CC=CC=C1 OPVGPOZNTNYEGU-UHFFFAOYSA-N 0.000 description 1
- ZYLIOSMVBRESMC-UHFFFAOYSA-N [4-(2-phenylethyl)phenyl] prop-2-enoate Chemical compound C(C=C)(=O)OC1=CC=C(C=C1)CCC1=CC=CC=C1 ZYLIOSMVBRESMC-UHFFFAOYSA-N 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- QHOTVLWYQNKORC-UHFFFAOYSA-N aminomethyl prop-2-enoate Chemical compound NCOC(=O)C=C QHOTVLWYQNKORC-UHFFFAOYSA-N 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 239000003960 organic solvent Substances 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
- 239000000049 pigment Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
- C07C69/54—Acrylic acid esters; Methacrylic acid esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C219/02—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C219/04—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C219/08—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having at least one of the hydroxy groups esterified by a carboxylic acid having the esterifying carboxyl group bound to an acyclic carbon atom of an acyclic unsaturated carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polymerisation Methods In General (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2009085492 | 2009-03-31 | ||
| JP2009085493 | 2009-03-31 | ||
| JP2009085492 | 2009-03-31 | ||
| JP2009085493 | 2009-03-31 | ||
| PCT/JP2010/053860 WO2010113600A1 (fr) | 2009-03-31 | 2010-03-09 | Dérivé d'ester de type (méth)acrylate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP4645925B2 true JP4645925B2 (ja) | 2011-03-09 |
| JPWO2010113600A1 JPWO2010113600A1 (ja) | 2012-10-11 |
Family
ID=42827900
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010523636A Active JP4645925B2 (ja) | 2009-03-31 | 2010-03-09 | （メタ）アクリル酸エステル誘導体 |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JP4645925B2 (fr) |
| TW (1) | TW201041847A (fr) |
| WO (1) | WO2010113600A1 (fr) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013136410A1 (fr) * | 2012-03-12 | 2013-09-19 | Dic株式会社 | Composition pouvant être polymérisée par voie radicalaire, produit durci obtenu à partir de celle-ci et lentille en plastique obtenue à partir de celle-ci |
| KR20140012581A (ko) * | 2011-05-18 | 2014-02-03 | 디아이씨 가부시끼가이샤 | 라디칼 중합성 조성물, 경화물 및 플라스틱 렌즈 |
| KR20140020710A (ko) * | 2011-06-13 | 2014-02-19 | 디아이씨 가부시끼가이샤 | 라디칼 중합성 조성물, 경화물 및 플라스틱 렌즈 |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5350055B2 (ja) * | 2009-04-14 | 2013-11-27 | 電気化学工業株式会社 | 接着剤用（メタ）アクリル系樹脂組成物 |
| JP5753721B2 (ja) * | 2011-04-11 | 2015-07-22 | 共栄社化学株式会社 | 光学材料用樹脂組成物及びその成形体 |
| SG194729A1 (en) * | 2011-05-13 | 2013-12-30 | 3M Innovative Properties Co | Benzyl (meth)acrylate monomers suitable for microstructured optical films |
| CN105008966B (zh) * | 2012-09-20 | 2019-12-03 | 3M创新有限公司 | 包含纳米颗粒和含有亚烷基氧重复单元的单体的微结构化膜 |
| JP6848213B2 (ja) * | 2016-05-31 | 2021-03-24 | 三菱ケミカル株式会社 | 光学部材用硬化性樹脂組成物、光学部材用樹脂、光学部材、レンズ及びカメラモジュール |
| WO2019189566A1 (fr) | 2018-03-28 | 2019-10-03 | クラレノリタケデンタル株式会社 | Composition de résine photodurcissable |
| JP7302133B2 (ja) * | 2019-03-28 | 2023-07-04 | 三井化学株式会社 | 光学材料用光硬化性組成物、光学材料及びレンズ |
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- 2010-03-09 WO PCT/JP2010/053860 patent/WO2010113600A1/fr active Application Filing
- 2010-03-09 JP JP2010523636A patent/JP4645925B2/ja active Active
- 2010-03-30 TW TW99109497A patent/TW201041847A/zh unknown
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| JPH0641447A (ja) * | 1991-04-29 | 1994-02-15 | Sandoz Ag | 非線形光学特性を有する化合物 |
| JPH0558950A (ja) * | 1991-06-21 | 1993-03-09 | Nippon Kayaku Co Ltd | （メタ）アクリル酸エステル |
| JPH06134772A (ja) * | 1992-10-23 | 1994-05-17 | Hitachi Ltd | 光学部品 |
| JPH09321864A (ja) * | 1996-05-31 | 1997-12-12 | Sanyo Electric Co Ltd | 電話機 |
| JPH1036317A (ja) * | 1996-07-23 | 1998-02-10 | Seiko Epson Corp | ジビフェニル誘導体および高分子分散型液晶表示素子 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20140012581A (ko) * | 2011-05-18 | 2014-02-03 | 디아이씨 가부시끼가이샤 | 라디칼 중합성 조성물, 경화물 및 플라스틱 렌즈 |
| US9156931B2 (en) * | 2011-05-18 | 2015-10-13 | Dic Corporation | Radical polymerizable composition, cured product, and plastic lens |
| KR101864631B1 (ko) * | 2011-05-18 | 2018-06-07 | 디아이씨 가부시끼가이샤 | 라디칼 중합성 조성물, 경화물 및 플라스틱 렌즈 |
| KR20140020710A (ko) * | 2011-06-13 | 2014-02-19 | 디아이씨 가부시끼가이샤 | 라디칼 중합성 조성물, 경화물 및 플라스틱 렌즈 |
| US8912300B2 (en) * | 2011-06-13 | 2014-12-16 | Dic Corporation | Radical polymerizable composition, cured product, and plastic lens |
| KR101864632B1 (ko) * | 2011-06-13 | 2018-06-07 | 디아이씨 가부시끼가이샤 | 라디칼 중합성 조성물, 경화물 및 플라스틱 렌즈 |
| WO2013136410A1 (fr) * | 2012-03-12 | 2013-09-19 | Dic株式会社 | Composition pouvant être polymérisée par voie radicalaire, produit durci obtenu à partir de celle-ci et lentille en plastique obtenue à partir de celle-ci |
Also Published As
| Publication number | Publication date |
|---|---|
| JPWO2010113600A1 (ja) | 2012-10-11 |
| WO2010113600A1 (fr) | 2010-10-07 |
| TW201041847A (en) | 2010-12-01 |
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