JP2022514270A - 高屈折率組成物およびその使用 - Google Patents
高屈折率組成物およびその使用 Download PDFInfo
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- JP2022514270A JP2022514270A JP2021534701A JP2021534701A JP2022514270A JP 2022514270 A JP2022514270 A JP 2022514270A JP 2021534701 A JP2021534701 A JP 2021534701A JP 2021534701 A JP2021534701 A JP 2021534701A JP 2022514270 A JP2022514270 A JP 2022514270A
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- Prior art keywords
- meth
- acryloyl
- composition
- terminal
- monomer
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- 239000000203 mixture Substances 0.000 title claims abstract description 190
- 239000000178 monomer Substances 0.000 claims abstract description 180
- 239000000376 reactant Substances 0.000 claims abstract description 108
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 59
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 43
- 150000003254 radicals Chemical class 0.000 claims abstract description 40
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 32
- 239000003999 initiator Substances 0.000 claims abstract description 24
- -1 acryloyloxy group Chemical group 0.000 claims description 90
- 239000007795 chemical reaction product Substances 0.000 claims description 63
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 49
- 238000006116 polymerization reaction Methods 0.000 claims description 31
- 229910052717 sulfur Inorganic materials 0.000 claims description 30
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 24
- 239000000463 material Substances 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 24
- 239000011593 sulfur Substances 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 150000003573 thiols Chemical class 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 19
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 238000000465 moulding Methods 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 150000001412 amines Chemical class 0.000 claims description 9
- 239000000049 pigment Substances 0.000 claims description 9
- 239000001294 propane Substances 0.000 claims description 9
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 claims description 9
- BGHCVCJVXZWKCC-UHFFFAOYSA-N tetradecane Chemical compound CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 7
- 239000012963 UV stabilizer Substances 0.000 claims description 7
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 238000010146 3D printing Methods 0.000 claims description 5
- 239000012760 heat stabilizer Substances 0.000 claims description 5
- LBROROBTVMUJEB-UHFFFAOYSA-N s-[2-[2-(2-methylprop-2-enoylsulfanyl)ethylsulfanyl]ethyl] 2-methylprop-2-enethioate Chemical group CC(=C)C(=O)SCCSCCSC(=O)C(C)=C LBROROBTVMUJEB-UHFFFAOYSA-N 0.000 claims description 5
- CEUQYYYUSUCFKP-UHFFFAOYSA-N 2,3-bis(2-sulfanylethylsulfanyl)propane-1-thiol Chemical compound SCCSCC(CS)SCCS CEUQYYYUSUCFKP-UHFFFAOYSA-N 0.000 claims description 4
- WECFIVGVCXMFHY-UHFFFAOYSA-N 2,3-bis[2-(2-sulfanylethylsulfanyl)ethylsulfanyl]propan-1-ol Chemical compound SCCSCCSC(CO)CSCCSCCS WECFIVGVCXMFHY-UHFFFAOYSA-N 0.000 claims description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 4
- 239000007983 Tris buffer Substances 0.000 claims description 4
- 239000006096 absorbing agent Substances 0.000 claims description 4
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- WNPSAOYKQQUALV-UHFFFAOYSA-N 1,3-bis(sulfanyl)propan-2-ol Chemical compound SCC(O)CS WNPSAOYKQQUALV-UHFFFAOYSA-N 0.000 claims description 3
- MTZVWTOVHGKLOX-UHFFFAOYSA-N 2,2-bis(sulfanylmethyl)propane-1,3-dithiol Chemical compound SCC(CS)(CS)CS MTZVWTOVHGKLOX-UHFFFAOYSA-N 0.000 claims description 3
- KSJBMDCFYZKAFH-UHFFFAOYSA-N 2-(2-sulfanylethylsulfanyl)ethanethiol Chemical group SCCSCCS KSJBMDCFYZKAFH-UHFFFAOYSA-N 0.000 claims description 3
- AJHCCBBKTPDSNT-UHFFFAOYSA-N 2-ethyl-2-(sulfanylmethyl)propane-1,3-dithiol Chemical compound CCC(CS)(CS)CS AJHCCBBKTPDSNT-UHFFFAOYSA-N 0.000 claims description 3
- NBUVVXNTRSKQSQ-UHFFFAOYSA-N 2-sulfanylpropane-1,3-diol Chemical compound OCC(S)CO NBUVVXNTRSKQSQ-UHFFFAOYSA-N 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 3
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- VSSFYDMUTATOHG-UHFFFAOYSA-N 2-(2-sulfanylethylsulfanyl)-3-[3-sulfanyl-2-(2-sulfanylethylsulfanyl)propyl]sulfanylpropane-1-thiol Chemical compound SCCSC(CS)CSCC(CS)SCCS VSSFYDMUTATOHG-UHFFFAOYSA-N 0.000 claims description 2
- 230000000996 additive effect Effects 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 abstract description 45
- 230000003287 optical effect Effects 0.000 abstract description 16
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- 125000000217 alkyl group Chemical group 0.000 description 24
- 150000001875 compounds Chemical class 0.000 description 24
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- 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 10
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- 150000001335 aliphatic alkanes Chemical class 0.000 description 8
- 125000003342 alkenyl group Chemical group 0.000 description 8
- 125000003545 alkoxy group Chemical group 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
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- 238000013001 point bending Methods 0.000 description 7
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
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- 239000003112 inhibitor Substances 0.000 description 6
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 6
- 238000007348 radical reaction Methods 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- JGQWAOHIXRWNIY-UHFFFAOYSA-N s-[[5-(2-methylprop-2-enoylsulfanylmethyl)-1,4-dithian-2-yl]methyl] 2-methylprop-2-enethioate Chemical group CC(=C)C(=O)SCC1CSC(CSC(=O)C(C)=C)CS1 JGQWAOHIXRWNIY-UHFFFAOYSA-N 0.000 description 6
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- YKFLAYDHMOASIY-UHFFFAOYSA-N γ-terpinene Chemical compound CC(C)C1=CCC(C)=CC1 YKFLAYDHMOASIY-UHFFFAOYSA-N 0.000 description 6
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- XESZUVZBAMCAEJ-UHFFFAOYSA-N 4-tert-butylcatechol Chemical compound CC(C)(C)C1=CC=C(O)C(O)=C1 XESZUVZBAMCAEJ-UHFFFAOYSA-N 0.000 description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 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 4
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- FZYCEURIEDTWNS-UHFFFAOYSA-N prop-1-en-2-ylbenzene Chemical compound CC(=C)C1=CC=CC=C1.CC(=C)C1=CC=CC=C1 FZYCEURIEDTWNS-UHFFFAOYSA-N 0.000 description 4
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- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
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- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 125000004404 heteroalkyl group Chemical group 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- AHAREKHAZNPPMI-UHFFFAOYSA-N hexa-1,3-diene Chemical compound CCC=CC=C AHAREKHAZNPPMI-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- ICIWUVCWSCSTAQ-UHFFFAOYSA-N iodic acid Chemical class OI(=O)=O ICIWUVCWSCSTAQ-UHFFFAOYSA-N 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000001034 iron oxide pigment Substances 0.000 description 1
- DCYOBGZUOMKFPA-UHFFFAOYSA-N iron(2+);iron(3+);octadecacyanide Chemical compound [Fe+2].[Fe+2].[Fe+2].[Fe+3].[Fe+3].[Fe+3].[Fe+3].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] DCYOBGZUOMKFPA-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- DZVCFNFOPIZQKX-LTHRDKTGSA-M merocyanine Chemical compound [Na+].O=C1N(CCCC)C(=O)N(CCCC)C(=O)C1=C\C=C\C=C/1N(CCCS([O-])(=O)=O)C2=CC=CC=C2O\1 DZVCFNFOPIZQKX-LTHRDKTGSA-M 0.000 description 1
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000001421 myristyl 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])[H] 0.000 description 1
- MXHTZQSKTCCMFG-UHFFFAOYSA-N n,n-dibenzyl-1-phenylmethanamine Chemical compound C=1C=CC=CC=1CN(CC=1C=CC=CC=1)CC1=CC=CC=C1 MXHTZQSKTCCMFG-UHFFFAOYSA-N 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920000779 poly(divinylbenzene) Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- CHWRSCGUEQEHOH-UHFFFAOYSA-N potassium oxide Chemical compound [O-2].[K+].[K+] CHWRSCGUEQEHOH-UHFFFAOYSA-N 0.000 description 1
- 229910001950 potassium oxide Inorganic materials 0.000 description 1
- ARJOQCYCJMAIFR-UHFFFAOYSA-N prop-2-enoyl prop-2-enoate Chemical compound C=CC(=O)OC(=O)C=C ARJOQCYCJMAIFR-UHFFFAOYSA-N 0.000 description 1
- KOPQZJAYZFAPBC-UHFFFAOYSA-N propanoyl propaneperoxoate Chemical class CCC(=O)OOC(=O)CC KOPQZJAYZFAPBC-UHFFFAOYSA-N 0.000 description 1
- 229960003351 prussian blue Drugs 0.000 description 1
- 239000013225 prussian blue Substances 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 description 1
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- FJELNSIPDYXDQA-UHFFFAOYSA-N s-[2-(2-prop-2-enoylsulfanylethylsulfanyl)ethyl] prop-2-enethioate Chemical compound C=CC(=O)SCCSCCSC(=O)C=C FJELNSIPDYXDQA-UHFFFAOYSA-N 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 229930006978 terpinene Natural products 0.000 description 1
- 150000003507 terpinene derivatives Chemical class 0.000 description 1
- PFBLRDXPNUJYJM-UHFFFAOYSA-N tert-butyl 2-methylpropaneperoxoate Chemical compound CC(C)C(=O)OOC(C)(C)C PFBLRDXPNUJYJM-UHFFFAOYSA-N 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
- 238000012360 testing method Methods 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical group CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 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
- QOPBTFMUVTXWFF-UHFFFAOYSA-N tripropyl phosphite Chemical compound CCCOP(OCCC)OCCC QOPBTFMUVTXWFF-UHFFFAOYSA-N 0.000 description 1
- KCTAHLRCZMOTKM-UHFFFAOYSA-N tripropylphosphane Chemical compound CCCP(CCC)CCC KCTAHLRCZMOTKM-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Images
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- C08F228/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a bond to sulfur or by a heterocyclic ring containing sulfur
- C08F228/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a bond to sulfur or by a heterocyclic ring containing sulfur by a bond to sulfur
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- B29D11/00009—Production of simple or compound lenses
- B29D11/00413—Production of simple or compound lenses made by moulding between two mould parts which are not in direct contact with one another, e.g. comprising a seal between or on the edges
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B29D11/00—Producing optical elements, e.g. lenses or prisms
- B29D11/00009—Production of simple or compound lenses
- B29D11/00432—Auxiliary operations, e.g. machines for filling the moulds
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- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/12—Esters of phenols or saturated alcohols
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- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
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- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
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Abstract
Description
本出願は、2018年12月18日に出願された、米国仮出願第62/781,344号明細書、および2019年11月6日に出願された米国仮出願第62/931,235号明細書(参照により、それらの全体が本明細書に援用される)に対する優先権の利益を主張する。
(メタ)アクリロイル-末端モノマーとオリゴマーの組み合わせを含む組成物は、活性水素基を有する反応物とアクリレート化剤を共反応させることによって調製される。この(メタ)アクリロイル-末端モノマーとオリゴマーの組み合わせを使用して形成された重合物は、高い硬度、優秀な熱機械特性、および高い屈折率を示す。この組成物は、光学コンポーネントを製作するために使用することができる。
高硫黄含量の重合性組成物は、光学コンポーネントを形成するために有用である。この重合性組成物は、典型的には、フリーラジカル存在下で反応する(メタ)アクリロイル-末端モノマーを含有する。この(メタ)アクリロイル-末端モノマーは、末端活性水素を含有する個々の反応物とアクリレート化剤を反応させることによって調製することができる。この反応は、活性水素基と、前記アクリレート化剤の(メタ)アクリロイル基のアルケニルとの反応によって形成される不溶性オリゴマーの形成によって、低収率になることがあり得る。
本発明によれば、組成物は、
(a)第1の(メタ)アクリロイル-末端モノマー(ここで、前記第1の(メタ)アクリロイル-末端モノマーは、式(1):
各R1は、水素またはメチルから独立して選択され;
bは、0または1から選択され;そして
aは、1~6の整数である)の構造を有する);および
(b)2つまたはそれを超える(メタ)アクリロイル基を含む第2の(メタ)アクリロイル-末端モノマー(ここで、
前記2つまたはそれを超える(メタ)アクリロイル基は、それぞれ(メタ)アクリロイルオキシ基または(メタ)アクリロイルチオ基から独立して選択され;
前記(メタ)アクリロイル基の少なくとも1つは、(メタ)アクリロイルチオ基であり;そして
前記第2の(メタ)アクリロイル-末端モノマー(b)は、前記第1の(メタ)アクリロイル-末端モノマーとは異なる)
を含む。
(i)2つの活性水素基を有する第1の反応物(前記第1の反応物は、式(5):
(ii)2つまたはそれを超える活性水素基を含む第2の反応物(ここで、
前記2つまたはそれを超える活性水素基は、それぞれヒドロキシルまたはチオールから独立して選択され;
前記2つまたはそれを超える活性水素基の少なくとも1つは、チオールであり;そして
前記第2の反応物は、前記第1の反応物とは異なる);および
(iii)アクリレート化剤を含む第3の反応物
を含む反応物の反応生成物を含む。
(A)反応物(i)、反応物(ii)、および反応物(iii)を合わせて混合物を形成すること(ここで、前記反応物は:
(i)2つの活性水素基を有する第1の反応物(前記第1の反応物は、式(5):
(ii)2つまたはそれを超える活性水素基を含む第2の反応物(ここで、
前記2つまたはそれを超える活性水素基は、それぞれヒドロキシルまたはチオールから独立して選択され;
前記2つまたはそれを超える活性水素基の少なくとも1つは、チオールであり;そして
前記第2の反応物は、前記第1の反応物とは異なる);および
(iii)第3の反応物(ここで、前記第3の反応物は、アクリレート化剤を含む);および
(B)塩基存在下で、前記混合物を反応させ、(メタ)アクリロイル-末端モノマーと(メタ)アクリロイル-末端オリゴマーの組み合わせを得ること、
を含む。
下記の詳細な説明の目的で、本開示によって提供される実施形態は、別段の明確な指示がある場合を除き、種々の代替的な変形形態およびステップの順序が想定され得ることを理解すべきである。さらに、作業実施例のいずれかにおける場合の他、または別段の記載がある場合を除き、例えば本明細書または特許請求の範囲で用いられている成分の量などを表す全ての数字は、全ての場合において、用語「約」によって修飾されているものとして理解すべきである。よって、これに反する記載がない限り、下記の詳細な説明および添付の特許請求の範囲に記載されている数的パラメーターは、本発明によって得ようとする所望の特性に応じて変わり得る概数である。少なくとも、かつ特許請求の範囲の範囲に対する均等論の適用を制限しようとするものではないが、各数的パラメーターは、少なくとも、報告された有効数字の数値を考慮し、かつ通常の数値の丸め技術を適用することによって解釈すべきである。
の構造を有する(メタ)アクリロイル-末端モノマーを含んでいてもよい。
(式中、
zは、3~6の整数であり;
各R1は、水素またはメチルから独立して選択され;
各Xは、OまたはSから独立して選択され;そしてXの少なくとも1つは、Sであり;
R2は、(ヘテロシクロアルカン)アルカン-ジイル、C6-20ヘテロアルカンアレーン-ジイル、置換(ヘテロシクロアルカン)アルカン-ジイル、または置換C6-20ヘテロアルカンアレーン-ジイルから選択され;
R3は、C1-12アルカン-ジイル、C2-12ヘテロアルカン-ジイル、C5-12ヘテロシクロアルカン-ジイル、C6-12ヘテロアレーン-ジイル、(ヘテロシクロアルカン)アルカン-ジイル、C6-20ヘテロアルカンアレーン-ジイル、置換C2-12アルカン-ジイル、置換C2-12ヘテロアルカン-ジイル、置換C5-12ヘテロシクロアルカン-ジイル、置換C6-12ヘテロアレーン-ジイル、置換(ヘテロシクロアルカン)アルカン-ジイル、または置換C6-20ヘテロアルカンアレーン-ジイルから選択され;そして
Bは、多官能性の部分である。
(a)2つの活性水素基を有する第1の反応物(前記第1の反応物は、式(5):
(b)2つまたはそれを超える活性水素基を含む第2の反応物(ここで、前記2つまたはそれを超える活性水素基は、それぞれヒドロキシルまたはチオールから独立して選択され;前記2つまたはそれを超える活性水素基の少なくとも1つは、チオールであり;そして前記第2の反応物は、前記第1の反応物とは異なる);および
(c)アクリレート化剤を含む第3の反応物
を含む反応物の反応生成物を含む。
(式中、
zは、3~6の整数であり;
各Xは、OまたはSから独立して選択され;そしてXの少なくとも1つは、Sであり;そして
R2は、(ヘテロシクロアルカン)アルカン-ジイル、C6-20ヘテロアルカンアレーン-ジイル、置換(ヘテロシクロアルカン)アルカン-ジイル、または置換C6-20ヘテロアルカンアレーン-ジイルから選択され;
R3は、C1-12アルカン-ジイル、C2-12ヘテロアルカン-ジイル、C5-12ヘテロシクロアルカン-ジイル、C6-12ヘテロアレーン-ジイル、(ヘテロシクロアルカン)アルカン-ジイル、C6-20ヘテロアルカンアレーン-ジイル、置換C2-12アルカン-ジイル、置換C2-12ヘテロアルカン-ジイル、置換C5-12ヘテロシクロアルカン-ジイル、置換C6-12ヘテロアレーン-ジイル、置換(ヘテロシクロアルカン)アルカン-ジイル、または置換C6-20ヘテロアルカンアレーン-ジイルから選択され;そして
Bは、多官能性の部分である。
(A)反応物(i)、反応物(ii)、および反応物(iii)を合わせて混合物を形成すること(ここで、前記反応物は:
(i)2つの活性水素基を有する第1の反応物(前記第1の反応物は、式(5):
(ii)2つまたはそれを超える活性水素基を含む第2の反応物(ここで、
前記2つまたはそれを超える活性水素基は、それぞれヒドロキシルまたはチオールから選択され;
前記2つまたはそれを超える活性水素基の少なくとも1つは、チオールであり;そして
前記第2の反応物(ii)は、前記第1の反応物(i)とは異なる);および
(iii)第3の反応物(ここで、前記第3の反応物は、アクリレート化剤を含む);および
(B)塩基存在下で、前記混合物を反応させ、(メタ)アクリロイル-末端モノマーと(メタ)アクリロイル-末端オリゴマーの組み合わせを得ること、
を含む。
に従って算出してもよい。
本発明の態様
(a)第1の(メタ)アクリロイル-末端モノマー(ここで、前記第1の(メタ)アクリロイル-末端モノマーは、式(1):
各R1は、水素またはメチルから独立して選択され;
bは、0または1から選択され;そして
aは、1~6の整数である)の構造を有する);および
(b)2つまたはそれを超える(メタ)アクリロイル基を含む第2の(メタ)アクリロイル-末端モノマー(ここで、
前記2つまたはそれを超える(メタ)アクリロイル基は、それぞれ(メタ)アクリロイルオキシ基または(メタ)アクリロイルチオ基から独立して選択され;
前記(メタ)アクリロイル基の少なくとも1つは、(メタ)アクリロイルチオ基であり;そして
前記第2の(メタ)アクリロイル-末端モノマー(b)は、前記第1の(メタ)アクリロイル-末端モノマー(a)とは異なる)
を含む、組成物。
(i)2つの活性水素基を有する第1の反応物(前記第1の反応物は、式(5):
(ii)2つまたはそれを超える活性水素基を含む第2の反応物(ここで、
前記2つまたはそれを超える活性水素基は、それぞれヒドロキシルまたはチオールから独立して選択され;
前記2つまたはそれを超える活性水素基の少なくとも1つは、チオールであり;そして
前記第2の反応物は、前記第1の反応物とは異なる);および
(iii)アクリレート化剤を含む第3の反応物
を含む反応物の反応生成物を含む、組成物。
(A)反応物(i)、反応物(ii)、および反応物(iii)を合わせて混合物を形成すること(ここで、前記反応物は:
(i)2つの活性水素基を有する第1の反応物(前記第1の反応物は、式(5):
(ii)2つまたはそれを超える活性水素基を含む第2の反応物(ここで、
前記2つまたはそれを超える活性水素基は、それぞれヒドロキシルまたはチオールから独立して選択され;
前記2つまたはそれを超える活性水素基の少なくとも1つは、チオールであり;そして
前記第2の反応物は、前記第1の反応物とは異なる);および
(iii)第3の反応物(ここで、前記第3の反応物は、アクリレート化剤を含む);および
(B)塩基存在下で、前記混合物を反応させ、(メタ)アクリロイル-末端モノマーと(メタ)アクリロイル-末端オリゴマーの組み合わせを得ること、
を含む、方法。
パート1
(メタ)アクリロイル-末端モノマーとオリゴマーの合成
レンズ成形
パート3
物理的特性の測定
フィッシャー微小硬度
E’貯蔵弾性率
屈折率およびアッベ数
に従って算出した。アッベ数は、「Abbe」として報告された。
GPC分子量分布分析
Claims (26)
- (a)第1の(メタ)アクリロイル-末端モノマー(ここで、前記第1の(メタ)アクリロイル-末端モノマーは、式(1):
各R1は、水素またはメチルから独立して選択され;
bは、0または1から選択され;そして
aは、1~6の整数である)の構造を有する);および
(b)2つまたはそれを超える(メタ)アクリロイル基を含む第2の(メタ)アクリロイル-末端モノマー(ここで、
前記2つまたはそれを超える(メタ)アクリロイル基は、それぞれ(メタ)アクリロイルオキシ基または(メタ)アクリロイルチオ基から独立して選択され;
前記(メタ)アクリロイル基の少なくとも1つは、(メタ)アクリロイルチオ基であり;そして
前記第2の(メタ)アクリロイル-末端モノマー(b)は、前記第1の(メタ)アクリロイル-末端モノマー(a)とは異なる)
を含む、組成物。 - aが、1または2から選択される、請求項1の組成物。
- 前記第2の(メタ)アクリロイル-末端モノマーが、ポリチアアルキレン部分を含む、請求項1の組成物。
- 前記ポリチアアルキレン部分が、環状ポリチアアルキレン部分または分枝ポリチアアルキレン部分である、請求項4の組成物。
- 前記ポリチアアルキレン部分が、分枝ポリチアアルキレン部分であり、そして前記第2の(メタ)アクリロイル-末端モノマーが、3~6個の(メタ)アクリロイル基を含む、請求項4の組成物。
- 前記第2の(メタ)アクリロイル-末端モノマーが、少なくとも1つの(メタ)アクリロイルチオ基と、少なくとも1つの(メタ)アクリロイルオキシ基を含む、請求項1の組成物。
- 前記第2の(メタ)アクリロイル-末端モノマーが、2,5-ビス[(メタ)アクリロイルチオメチル]-1,4-ジチアン、4-(メタ)アクリロイルチオメチル-3,6-ジチア-1,8-ビス[(メタ)アクリロイルチオ]オクタン、7-(メタ)アクリロイルオキシメチル-3,6,9,12-テトラチア-1,14-ビス[(メタ)アクリロイルチオ]テトラデカン、4,8-ビス[(メタ)アクリロイルチオメチル]-3,6,9-トリチア-1,11-ビス[(メタ)アクリロイルチオ]ウンデカンならびにその4,7-および5,7-位置異性体などの位置異性体、2-エチル-2-((メタ)アクリロイルチオメチル)-1,3-ビス[(メタ)アクリロイルチオ]プロパン、1,2,3-トリス[(メタ)アクリロイルチオ]プロパン、または上記の任意のものの組み合わせを含む、請求項1の組成物。
- 前記組成物が、(メタ)アクリロイル-末端オリゴマーをさらに含む、請求項1の組成物。
- 前記組成物が、15wt%~60wt%の硫黄を含む(ここで、wt%は、前記組成物の総重量に基づく)、請求項1の組成物。
- 前記第1の(メタ)アクリロイル-末端モノマーが、第1の(メタ)アクリロイル当量を含み;
前記第2の(メタ)アクリロイル-末端モノマーが、第2の(メタ)アクリロイル当量を含み;そして
前記第1の(メタ)アクリロイル当量と前記第2の(メタ)アクリロイル当量の比が、1:1を超える、
請求項1の組成物。 - フリーラジカル開始剤をさらに含み、前記フリーラジカル開始剤が、光開始剤または熱活性化フリーラジカル開始剤を含む、請求項1の重合性組成物。
- 少なくとも1つの第3のモノマーをさらに含み、
前記第3のモノマーが、1つまたはそれを超えるエチレン性不飽和ラジカル重合性基を含み;そして
前記第3のモノマーが、前記第1の(メタ)アクリロイル-末端モノマーとも、前記第2の(メタ)アクリロイル-末端モノマーとも異なる、
請求項1の重合性組成物。 - 前記重合性組成物が、熱安定剤、UV安定剤、UV吸収剤、ヒンダードアミン光安定剤、二色性材料、フォトクロミック材料、重合減速剤、重合促進剤、顔料、染料、または上記の任意のものの組み合わせのうちの1つまたはそれを超えるものをさらに含む、請求項1の重合性組成物。
- 前記重合促進剤が、オルガノホスフィン、オルガノホスファイト、アミン、またはそれらの組み合わせを含んでいてもよい、請求項14の重合性組成物。
- aが、1または2から選択される、請求項16の組成物。
- 前記第2の反応物が、2,5-ジメルカプトメチル-1,4-ジチアン、2-エチル-2-(メルカプトメチル)プロパン-1,3-ジチオール、1,2,3-トリメルカプトプロパン、2,2-ビス(メルカプトメチル)プロパン-1,3-ジチオール、4-メルカプトメチル-3,6-ジチア-1,8-オクタンジチオール、1,3-ジメルカプト-2-プロパノール、3-メルカプト-1,2-プロパンジオール、2-メルカプト-1,3-プロパンジオール、2,3-ジメルカプト-1-プロパノール、7-ヒドロキシメチル-1,14-ジメルカプト-3,6,9,12-テトラチアテトラデカン、4,8-ビス(メルカプトメチル)-1,11-ジメルカプト-3,6,9-トリチアウンデカンならびにその4,7-および5,7-位置異性体などの位置異性体、または上記の任意のものの組み合わせを含む、請求項16の組成物。
- 前記アクリレート化剤が、塩化(メタ)アクリロイルまたは(メタ)アクリル酸無水物を含む、請求項16の組成物。
- 前記第1の反応物の活性水素基当量と、前記第2の反応物の活性水素基当量の比が、1:1を超える、請求項16の組成物。
- 前記反応生成物が、
第1の(メタ)アクリロイル-末端モノマー(ここで、前記第1の(メタ)アクリロイル-末端モノマーは、前記第1の反応物に由来する);
第2の(メタ)アクリロイル-末端モノマー(ここで、前記第2の(メタ)アクリロイル-末端モノマーは、前記第2の反応物に由来する);および
(メタ)アクリロイル-末端オリゴマーの組み合わせ(ここで、前記(メタ)アクリロイル-末端オリゴマーの組み合わせは、前記第1の反応物と、前記第2の反応物と、前記アクリレート化剤との反応に由来する)
を含む、請求項16の組成物。 - 前記組成物が、15wt%~60wt%の硫黄を含む(ここで、wt%は、前記組成物の総重量に基づく)、請求項16の組成物。
- フリーラジカル開始剤をさらに含み、前記フリーラジカル開始剤が、光開始剤または熱活性化フリーラジカル開始剤を含む、請求項16の重合性組成物。
- 物品を製作する方法であって、
請求項24の重合性組成物をある形状に成型すること、
ここで、成型することは、成形、付加製造、3Dプリンティング、インクジェット印刷、転写印刷、またはステレオリソグラフィーを含む;および
前記成型を施された組成物を硬化させて前記物品を得ること、
を含む、方法。 - 前記方法が、前記形状の成型前に、前記形状の成型後に、前記形状の成型中に、または上記の任意のものの組み合わせにおいて、前記組成物を化学線に曝露することを含む、請求項25の方法。
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