WO2016129563A1 - 重合性組成物および新規なアルキン化合物 - Google Patents
重合性組成物および新規なアルキン化合物 Download PDFInfo
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- WO2016129563A1 WO2016129563A1 PCT/JP2016/053703 JP2016053703W WO2016129563A1 WO 2016129563 A1 WO2016129563 A1 WO 2016129563A1 JP 2016053703 W JP2016053703 W JP 2016053703W WO 2016129563 A1 WO2016129563 A1 WO 2016129563A1
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- WIPO (PCT)
- Prior art keywords
- bis
- mercaptomethylthio
- group
- general formula
- compound
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- -1 alkyne compound Chemical class 0.000 title claims abstract description 118
- 239000000203 mixture Substances 0.000 title claims abstract description 109
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 27
- 229910052787 antimony Inorganic materials 0.000 claims abstract description 24
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical group [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims abstract description 19
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 18
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 17
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 17
- 125000005730 thiophenylene group Chemical group 0.000 claims abstract description 15
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 7
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 108
- 238000006116 polymerization reaction Methods 0.000 claims description 38
- 230000003287 optical effect Effects 0.000 claims description 26
- 239000000463 material Substances 0.000 claims description 17
- FDJWTMYNYYJBAT-UHFFFAOYSA-N 1,3,3-tris(sulfanylmethylsulfanyl)propylsulfanylmethanethiol Chemical compound SCSC(SCS)CC(SCS)SCS FDJWTMYNYYJBAT-UHFFFAOYSA-N 0.000 claims description 13
- 229920006295 polythiol Polymers 0.000 claims description 13
- CEUQYYYUSUCFKP-UHFFFAOYSA-N 2,3-bis(2-sulfanylethylsulfanyl)propane-1-thiol Chemical compound SCCSCC(CS)SCCS CEUQYYYUSUCFKP-UHFFFAOYSA-N 0.000 claims description 10
- OCGYTRZLSMAPQC-UHFFFAOYSA-N 3-(2-sulfanylethylsulfanyl)-2-[1-sulfanyl-3-(2-sulfanylethylsulfanyl)propan-2-yl]sulfanylpropane-1-thiol Chemical compound SCCSCC(CS)SC(CS)CSCCS OCGYTRZLSMAPQC-UHFFFAOYSA-N 0.000 claims description 9
- 239000004033 plastic Substances 0.000 claims description 9
- 229920003023 plastic Polymers 0.000 claims description 9
- KSJBMDCFYZKAFH-UHFFFAOYSA-N 2-(2-sulfanylethylsulfanyl)ethanethiol Chemical compound SCCSCCS KSJBMDCFYZKAFH-UHFFFAOYSA-N 0.000 claims description 6
- COYTVZAYDAIHDK-UHFFFAOYSA-N [5-(sulfanylmethyl)-1,4-dithian-2-yl]methanethiol Chemical compound SCC1CSC(CS)CS1 COYTVZAYDAIHDK-UHFFFAOYSA-N 0.000 claims description 6
- QNSUVMHSJGIMDL-UHFFFAOYSA-N [6-(sulfanylmethylsulfanyl)-1,3-dithian-4-yl]sulfanylmethanethiol Chemical compound SCSC1CC(SCS)SCS1 QNSUVMHSJGIMDL-UHFFFAOYSA-N 0.000 claims description 6
- RUDUCNPHDIMQCY-UHFFFAOYSA-N [3-(2-sulfanylacetyl)oxy-2,2-bis[(2-sulfanylacetyl)oxymethyl]propyl] 2-sulfanylacetate Chemical compound SCC(=O)OCC(COC(=O)CS)(COC(=O)CS)COC(=O)CS RUDUCNPHDIMQCY-UHFFFAOYSA-N 0.000 claims description 5
- JOBBTVPTPXRUBP-UHFFFAOYSA-N [3-(3-sulfanylpropanoyloxy)-2,2-bis(3-sulfanylpropanoyloxymethyl)propyl] 3-sulfanylpropanoate Chemical compound SCCC(=O)OCC(COC(=O)CCS)(COC(=O)CCS)COC(=O)CCS JOBBTVPTPXRUBP-UHFFFAOYSA-N 0.000 claims description 5
- NITQFNYRKUAWHQ-UHFFFAOYSA-N [2-(1,3-dithietan-2-yl)-1-(sulfanylmethylsulfanyl)ethyl]sulfanylmethanethiol Chemical compound SCSC(SCS)CC1SCS1 NITQFNYRKUAWHQ-UHFFFAOYSA-N 0.000 claims description 4
- 238000000034 method Methods 0.000 description 31
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- 238000001816 cooling Methods 0.000 description 28
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- 239000011521 glass Substances 0.000 description 24
- 239000000243 solution Substances 0.000 description 23
- 229920005989 resin Polymers 0.000 description 22
- 239000011347 resin Substances 0.000 description 22
- 238000004519 manufacturing process Methods 0.000 description 21
- 239000000126 substance Substances 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 14
- 238000003756 stirring Methods 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 238000001914 filtration Methods 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 239000013065 commercial product Substances 0.000 description 10
- 239000005457 ice water Substances 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 10
- 125000003396 thiol group Chemical group [H]S* 0.000 description 10
- 238000011282 treatment Methods 0.000 description 10
- 238000005160 1H NMR spectroscopy Methods 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 9
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 8
- 239000007983 Tris buffer Substances 0.000 description 7
- 125000002355 alkine group Chemical group 0.000 description 7
- 238000000465 moulding Methods 0.000 description 7
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- 239000002685 polymerization catalyst Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 239000011593 sulfur Substances 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- KDKYADYSIPSCCQ-UHFFFAOYSA-N but-1-yne Chemical compound CCC#C KDKYADYSIPSCCQ-UHFFFAOYSA-N 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 4
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- FAPDDOBMIUGHIN-UHFFFAOYSA-K antimony trichloride Chemical compound Cl[Sb](Cl)Cl FAPDDOBMIUGHIN-UHFFFAOYSA-K 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 150000007514 bases Chemical class 0.000 description 3
- BCBDIPGKPAERPG-UHFFFAOYSA-N but-3-yne-1-thiol Chemical compound SCCC#C BCBDIPGKPAERPG-UHFFFAOYSA-N 0.000 description 3
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 3
- 239000000920 calcium hydroxide Substances 0.000 description 3
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 3
- 238000002451 electron ionisation mass spectrometry Methods 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 150000007529 inorganic bases Chemical class 0.000 description 3
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 3
- 229910052808 lithium carbonate Inorganic materials 0.000 description 3
- HQRPHMAXFVUBJX-UHFFFAOYSA-M lithium;hydrogen carbonate Chemical compound [Li+].OC([O-])=O HQRPHMAXFVUBJX-UHFFFAOYSA-M 0.000 description 3
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 3
- 239000000347 magnesium hydroxide Substances 0.000 description 3
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 3
- INBDPOJZYZJUDA-UHFFFAOYSA-N methanedithiol Chemical compound SCS INBDPOJZYZJUDA-UHFFFAOYSA-N 0.000 description 3
- 239000006082 mold release agent Substances 0.000 description 3
- PQVSDXYMJDJOMG-UHFFFAOYSA-N o-prop-2-ynyl ethanethioate Chemical compound CC(=S)OCC#C PQVSDXYMJDJOMG-UHFFFAOYSA-N 0.000 description 3
- 150000007530 organic bases Chemical class 0.000 description 3
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 3
- 235000015497 potassium bicarbonate Nutrition 0.000 description 3
- 239000011736 potassium bicarbonate Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 235000011181 potassium carbonates Nutrition 0.000 description 3
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 3
- BHLUERUPCAAQGF-UHFFFAOYSA-N prop-2-yne-1-thiol Chemical compound SCC#C BHLUERUPCAAQGF-UHFFFAOYSA-N 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
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- SPAAESPYCDSRIW-UHFFFAOYSA-N 2-(2-sulfanylethyldisulfanyl)ethanethiol Chemical compound SCCSSCCS SPAAESPYCDSRIW-UHFFFAOYSA-N 0.000 description 2
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- ODJQKYXPKWQWNK-UHFFFAOYSA-N 3,3'-Thiobispropanoic acid Chemical compound OC(=O)CCSCCC(O)=O ODJQKYXPKWQWNK-UHFFFAOYSA-N 0.000 description 2
- YCLSOMLVSHPPFV-UHFFFAOYSA-N 3-(2-carboxyethyldisulfanyl)propanoic acid Chemical compound OC(=O)CCSSCCC(O)=O YCLSOMLVSHPPFV-UHFFFAOYSA-N 0.000 description 2
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- 239000004215 Carbon black (E152) Substances 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- ZERULLAPCVRMCO-UHFFFAOYSA-N Dipropyl sulfide Chemical compound CCCSCCC ZERULLAPCVRMCO-UHFFFAOYSA-N 0.000 description 2
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- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
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- 229940117389 dichlorobenzene Drugs 0.000 description 2
- LJSQFQKUNVCTIA-UHFFFAOYSA-N diethyl sulfide Chemical compound CCSCC LJSQFQKUNVCTIA-UHFFFAOYSA-N 0.000 description 2
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- 238000004043 dyeing Methods 0.000 description 2
- 239000003759 ester based solvent Substances 0.000 description 2
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
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- 238000000605 extraction Methods 0.000 description 2
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- 238000007710 freezing Methods 0.000 description 2
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 2
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- 150000002430 hydrocarbons Chemical class 0.000 description 2
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- 229910052740 iodine Inorganic materials 0.000 description 2
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- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 2
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
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- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
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- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- SUVIGLJNEAMWEG-UHFFFAOYSA-N propane-1-thiol Chemical compound CCCS SUVIGLJNEAMWEG-UHFFFAOYSA-N 0.000 description 2
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- KZCOBXFFBQJQHH-UHFFFAOYSA-N octane-1-thiol Chemical compound CCCCCCCCS KZCOBXFFBQJQHH-UHFFFAOYSA-N 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- UKQMUPLYHOXQQR-UHFFFAOYSA-N phenylmethanedithiol Chemical compound SC(S)C1=CC=CC=C1 UKQMUPLYHOXQQR-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000004714 phosphonium salts Chemical group 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 1
- RIZZXCJMFIGMON-UHFFFAOYSA-N prop-2-ynyl acetate Chemical compound CC(=O)OCC#C RIZZXCJMFIGMON-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- NCNISYUOWMIOPI-UHFFFAOYSA-N propane-1,1-dithiol Chemical compound CCC(S)S NCNISYUOWMIOPI-UHFFFAOYSA-N 0.000 description 1
- UWHMFGKZAYHMDJ-UHFFFAOYSA-N propane-1,2,3-trithiol Chemical compound SCC(S)CS UWHMFGKZAYHMDJ-UHFFFAOYSA-N 0.000 description 1
- ZJLMKPKYJBQJNH-UHFFFAOYSA-N propane-1,3-dithiol Chemical compound SCCCS ZJLMKPKYJBQJNH-UHFFFAOYSA-N 0.000 description 1
- HMPSOEYFMTWOFC-UHFFFAOYSA-N propane-2,2-dithiol Chemical compound CC(C)(S)S HMPSOEYFMTWOFC-UHFFFAOYSA-N 0.000 description 1
- 125000000177 propargylthio group Chemical group [H]C#CC([H])([H])S* 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical compound CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- SUBJHSREKVAVAR-UHFFFAOYSA-N sodium;methanol;methanolate Chemical compound [Na+].OC.[O-]C SUBJHSREKVAVAR-UHFFFAOYSA-N 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- FKPZDPMIYDBOJO-UHFFFAOYSA-N sulfanylmethylsulfanyl(sulfanylmethylsulfanylmethylsulfanyl)methanethiol Chemical compound SCSC(SCSCS)S FKPZDPMIYDBOJO-UHFFFAOYSA-N 0.000 description 1
- OOZWJYRXTAYWTJ-UHFFFAOYSA-N sulfanylmethylsulfanyl-[3-[3-(sulfanylmethylsulfanyl)propylsulfanylmethylsulfanyl]propylsulfanylmethylsulfanylmethylsulfanyl]methanethiol Chemical compound SCSCCCSCSCCCSCSCSC(S)SCS OOZWJYRXTAYWTJ-UHFFFAOYSA-N 0.000 description 1
- WTSBJMAOQNCZBF-UHFFFAOYSA-N sulfanylmethylsulfanylmethanethiol Chemical compound SCSCS WTSBJMAOQNCZBF-UHFFFAOYSA-N 0.000 description 1
- QNITWMBGUWZSSI-UHFFFAOYSA-N sulfanylmethylsulfanylmethylsulfanylmethanethiol Chemical compound SCSCSCS QNITWMBGUWZSSI-UHFFFAOYSA-N 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- DHBFIOQRWRNVNA-UHFFFAOYSA-N thietan-3-ylsulfanylmethanethiol Chemical compound SCSC1CSC1 DHBFIOQRWRNVNA-UHFFFAOYSA-N 0.000 description 1
- JWYUQPVSSAKHMX-UHFFFAOYSA-N thietane-2-thiol Chemical compound SC1CCS1 JWYUQPVSSAKHMX-UHFFFAOYSA-N 0.000 description 1
- 150000003552 thietanes Chemical class 0.000 description 1
- 125000002053 thietanyl group Chemical group 0.000 description 1
- CVHLOUDPCBXUES-UHFFFAOYSA-N thiiran-2-ylmethanethiol Chemical compound SCC1CS1 CVHLOUDPCBXUES-UHFFFAOYSA-N 0.000 description 1
- XUWKLJZTLIZVLP-UHFFFAOYSA-N thiiran-2-ylmethylsulfanylmethanethiol Chemical compound SCSCC1CS1 XUWKLJZTLIZVLP-UHFFFAOYSA-N 0.000 description 1
- 229940071127 thioglycolate Drugs 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- NJRXVEJTAYWCQJ-UHFFFAOYSA-N thiomalic acid Chemical compound OC(=O)CC(S)C(O)=O NJRXVEJTAYWCQJ-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- TWXMZYPORGXIFB-UHFFFAOYSA-N thiophene-3,4-dithiol Chemical compound SC1=CSC=C1S TWXMZYPORGXIFB-UHFFFAOYSA-N 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F38/00—Homopolymers and copolymers of compounds having one or more carbon-to-carbon triple bonds
- C08F38/02—Acetylene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
- C07C321/12—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/90—Antimony compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/02—Polythioethers
- C08G75/04—Polythioethers from mercapto compounds or metallic derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/02—Polythioethers
- C08G75/04—Polythioethers from mercapto compounds or metallic derivatives thereof
- C08G75/045—Polythioethers from mercapto compounds or metallic derivatives thereof from mercapto compounds and unsaturated compounds
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
- G02B1/041—Lenses
-
- G—PHYSICS
- G02—OPTICS
- G02C—SPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
- G02C7/00—Optical parts
- G02C7/02—Lenses; Lens systems ; Methods of designing lenses
Definitions
- the present invention relates to a polymerizable composition and a novel alkyne compound.
- Patent Document 1 describes an example using a compound having a disulfide bond. Further, Non-Patent Document 1 describes that optical properties are unknown, but a resin can be obtained by copolymerizing a compound having sulfur and a triple bond and polythiol.
- Patent Document 2 describes metal-containing thietane compounds. Further, an optical material having a high refractive index exceeding a refractive index (nd) of 1.7 is described. Patent Document 3 describes that an optical material having a high refractive index exceeding a refractive index (ne) of 1.8 was obtained by using an antimony ethane compound. Furthermore, Patent Document 4 describes that an optical material having a refractive index of 1.463 was obtained using an antimony allyl thiolate compound. Patent Document 5 describes that an optical material having a refractive index of 1.730 was obtained from a polymerizable composition containing propargyl isocyanate and a polythiol compound. Patent Document 6 and Non-Patent Documents 2 to 5 disclose compounds having triple bonds at both ends.
- An object of the present invention is to obtain a polymerizable composition containing a predetermined compound and a novel alkyne compound, which can obtain an optical material having a high refractive index.
- X 1 and X 2 each represents a sulfur atom, an oxygen atom, or an NH group, and may be the same or different.
- Q is an alkylene group having 1 to 2 carbon atoms, a carbonyl group, Or a thiophenylene group in which one of the carbon atoms is replaced with an antimony atom, R 1 and R 2 each represent an alkylene group having 1 to 2 carbon atoms, and may be the same or different, and m and n are each 0 Or 1).
- M and n each represents 0 or 1)
- X 1 and X 2 represent a sulfur atom, an oxygen atom, or an NH group, and may be the same or different.
- X 1 and X 2 represent a sulfur atom, an oxygen atom, or an NH group, and may be the same or different.
- X 1 and X 2 represent a sulfur atom, an oxygen atom, or an NH group, and may be the same or different.
- the thiol compound is 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 4,8 or 4,7 or 5,7-dimercaptomethyl-1,11-dimercapto-3,6 , 9-trithiaundecane, pentaerythritol tetrakis (2-mercaptoacetate), pentaerythritol tetrakis (3-mercaptopropionate), 2,5-bis (mercaptomethyl) -1,4-dithiane, bis (mercaptoethyl) Sulfide, 1,1,3,3-tetrakis (mercaptomethylthio) propane, 4,6-bis (mercaptomethylthio) -1,3-dithiane, 2- (2,2-bis (mercaptomethylthio) ethyl) -1,
- the compound according to [4] comprising one or more polythiol compounds selected from 3-dithietane.
- An optical material comprising the molded article according to [6].
- a plastic lens comprising the molded article according to [6].
- Q represents an alkylene group having 1 to 2 carbon atoms, a carbonyl group, or a carbon atom. One represents a thiophenylene group replaced by an antimony atom).
- the polymerizable composition according to the present invention includes an alkyne compound represented by the following general formula (1).
- X 1 and X 2 represent a sulfur atom, an oxygen atom, or an NH group, and may be the same or different.
- X 1 and X 2 can be a combination of sulfur atoms, a combination of sulfur atoms and NH groups, or a combination of oxygen atoms.
- Q represents an alkylene group having 1 to 2 carbon atoms, a carbonyl group, or a thiophenylene group in which one of carbon atoms is replaced with an antimony atom.
- the position of the antimony atom is not particularly limited. From the viewpoint of the effect of the present invention, a group represented by the following general formula (4) can be used.
- R 1 and R 2 each represent an alkylene group having 1 to 2 carbon atoms, and may be the same or different. R 1 and R 2 are preferably an alkylene group having 1 carbon atom. m and n each represents 0 or 1. According to the polymerizable composition containing such an alkyne compound, a transparent optical material having a high refractive index can be obtained.
- the alkyne compound is preferably a compound represented by the following general formula (2) or (3) from the viewpoint of the effect of the present invention.
- Q represents an alkylene group having 1 to 2 carbon atoms or a thiophenylene group in which one of carbon atoms is replaced with an antimony atom.
- m and n are synonymous with General formula (1).
- X 1 and X 2 have the same meanings as in general formula (1).
- the following compounds can be given as novel compounds.
- X 3 and X 4 represent a sulfur atom or an NH group, and a combination of sulfur or a combination of a sulfur atom and an NH group is preferable.
- Q has the same meaning as in general formula (1), and is preferably an alkylene group having 1 carbon atom, a carbonyl group, or a thiophenylene group in which one of carbon atoms is replaced with an antimony atom.
- alkyne compound represented by the general formula (1) compounds represented by the following general formulas (1-1) to (1-5) can be preferably used.
- R 1 , R 2 , Q, X 1 and X 2 have the same meaning as in the general formula (1). In this case, m is 1. These compounds can be obtained as follows.
- the compound represented by the general formula (1-1) can be obtained by dropping a halogenated alkyl compound having an alkyne group at a terminal into a solution obtained by mixing and stirring a dithiol compound and a basic compound.
- a basic compound as a scavenger for the generated hydrogen halide.
- Examples of such basic compounds include sodium hydroxide, potassium hydroxide, lithium hydroxide, sodium carbonate, potassium carbonate, lithium carbonate, sodium bicarbonate, potassium bicarbonate, lithium bicarbonate, magnesium hydroxide, and calcium hydroxide.
- Inorganic bases; and organic bases such as pyridine, triethylamine, dimethylaniline, diethylaniline, 1,8-diazabicyclo [5.4.0] -7-undecene.
- the compound represented by the general formula (1-2) can be obtained by adding an iodine solution dropwise to a stirred solution of a thioacetic acid ester compound having an alkyne group at the terminal and caustic water.
- the reaction and handling at a low temperature are desirable. Specifically, the operations from reaction to removal can be carried out at -20 ° C or higher and 10 ° C or lower.
- the compound represented by the general formula (1-3) can be obtained by dropping a halogenated alkyl compound having an alkyne group at a terminal into a solution obtained by mixing and stirring sodium sulfide and dimethylformamide.
- the reaction temperature of the compounds shown above is not particularly limited, but is usually in the range of ⁇ 78 ° C. or higher and 200 ° C. or lower, preferably ⁇ 78 ° C. or higher and 100 ° C. or lower.
- A represents a hydroxyl group, a thiol group, or an isocyanate group, which may be the same or different.
- the compound represented by the general formula (1-4) can be obtained by dropping a solution in which triphosgene or phosgene is dissolved and a mixture of an alcohol having an alkyne group or a thiol compound and a base into the solution. .
- it can be obtained by dropping an alcohol or thiol compound having an alkyne group at a terminal into a solution in which an isocyanate compound having an alkyne group is dissolved.
- the solvent that can be used in the above reaction is not particularly limited as long as it is an inert solvent for the reaction, and hydrocarbon solvents such as petroleum ether, hexane, benzene, toluene, xylene, mesitylene; Ether solvents such as diethyl ether, tetrahydrofuran, diethylene glycol dimethyl ether; Ketone solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone; Ester solvents such as ethyl acetate, butyl acetate, amyl acetate; Chlorine-containing solvents such as methylene chloride, chloroform, chlorobenzene, dichlorobenzene; Etc. are exemplified.
- hydrocarbon solvents such as petroleum ether, hexane, benzene, toluene, xylene, mesitylene
- Ether solvents such as diethyl ether,
- the base examples include inorganic bases such as sodium hydroxide, potassium hydroxide, lithium hydroxide, sodium carbonate, potassium carbonate, lithium carbonate, sodium bicarbonate, potassium bicarbonate, lithium bicarbonate, magnesium hydroxide, calcium hydroxide; Alkali metal alkoxides such as sodium methoxide, sodium ethoxide, potassium t-butoxide; and organic bases such as pyridine, triethylamine, dimethylaniline, diethylaniline, 1,8-diazabicyclo [5.4.0] -7-undecene; Etc.
- inorganic bases such as sodium hydroxide, potassium hydroxide, lithium hydroxide, sodium carbonate, potassium carbonate, lithium carbonate, sodium bicarbonate, potassium bicarbonate, lithium bicarbonate, magnesium hydroxide, calcium hydroxide
- Alkali metal alkoxides such as sodium methoxide, sodium ethoxide, potassium t-butoxide
- organic bases such as pyridine, triethyl
- the reaction temperature is not particularly limited, but is usually in the range of ⁇ 78 ° C. to 200 ° C., and preferably ⁇ 78 ° C. to 100 ° C.
- the reaction time is influenced by the reaction temperature, but is usually from several minutes to 100 hours.
- the compound represented by the general formula (1-5) is, for example, propylene or a thioacetylated product of 1-butyne, propargyl thiol or 3-butyne-1-thiol in the presence of a solvent and a base inert to the reaction, It can be obtained by acting antimony halide.
- the solvent that can be used in the above reaction is not particularly limited as long as it is an inert solvent for the reaction, and hydrocarbon solvents such as petroleum ether, hexane, benzene, toluene, xylene, mesitylene; Ether solvents such as diethyl ether, tetrahydrofuran, diethylene glycol dimethyl ether; Ketone solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone; Ester solvents such as ethyl acetate, butyl acetate, amyl acetate; Chlorine-containing solvents such as methylene chloride, chloroform, chlorobenzene, dichlorobenzene; Aprotic polar solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, N, N-dimethylimidazolidinone, dimethyl sulfoxide; Sulfur-containing solvents such as tetra
- the base examples include inorganic bases such as sodium hydroxide, potassium hydroxide, lithium hydroxide, sodium carbonate, potassium carbonate, lithium carbonate, sodium bicarbonate, potassium bicarbonate, lithium bicarbonate, magnesium hydroxide, calcium hydroxide; Alkali metal alkoxides such as sodium methoxide, sodium ethoxide, potassium t-butoxide; and organic bases such as pyridine, triethylamine, dimethylaniline, diethylaniline, 1,8-diazabicyclo [5.4.0] -7-undecene; Etc.
- inorganic bases such as sodium hydroxide, potassium hydroxide, lithium hydroxide, sodium carbonate, potassium carbonate, lithium carbonate, sodium bicarbonate, potassium bicarbonate, lithium bicarbonate, magnesium hydroxide, calcium hydroxide
- Alkali metal alkoxides such as sodium methoxide, sodium ethoxide, potassium t-butoxide
- organic bases such as pyridine, triethyl
- examples of the antimony halide that can be used in the present invention include antimony chloride and antimony bromide. From the viewpoint of easy availability, antimony chloride is preferable.
- the reaction temperature is not particularly limited, but is usually in the range of ⁇ 78 ° C. to 200 ° C., and preferably ⁇ 78 ° C. to 100 ° C.
- the reaction time is influenced by the reaction temperature, but is usually from several minutes to 100 hours.
- the amount of propyne or 1-butyne thioacetylated compound, propargylthiol or 3-butyne-1-thiol used in the above reaction is not particularly limited, but it is usually 1 mol of halogen atom contained in antimony halide.
- the amount of thioacetylated product, propargylthiol or 3-butyne-1-thiol used is 0.01 mol or more and 20 mol or less. Preferably, they are 0.1 mol or more and 5 mol or less, More preferably, they are 0.5 mol or more and 1.5 mol or less.
- alkyne compound represented by the general formula (1) compounds represented by the following formulas (1a) to (1h) can be preferably used.
- reaction schemes of the compounds of the formula (1a), the formula (1e), the formula (1f), the formula (1g), and the formula (1h) are shown as specific examples.
- NaOHaq represents an aqueous sodium hydroxide solution
- Ac represents an acetyl group
- the polymerizable composition of the present invention contains an alkyne compound represented by the general formula (1). Furthermore, a thiol compound can be contained together with this alkyne compound, and it can be suitably used as a polymerizable composition for optical materials.
- the thiol compound used in the polymerizable composition is a compound containing one or more thiol groups (SH groups) in the molecule.
- SH groups thiol groups
- a compound having any structure can be used as long as it is compatible with the compound represented by the general formula (1).
- thiol compound specifically, as a monovalent thiol compound, methyl mercaptan, ethyl mercaptan, propyl mercaptan, butyl mercaptan, octyl mercaptan, dodecyl mercaptan, tert-dodecyl mercaptan, hexadecyl mercaptan, octadecyl mercaptan, cyclohexyl mercaptan, benzyl Mercaptan, ethylphenyl mercaptan, 2-mercaptomethyl-1,3-dithiolane, 2-mercaptomethyl-1,4-dithiane, 1-mercapto-2,3-epithiopropane, 1-mercaptomethylthio-2,3-epi Thiopropane, 1-mercaptoethylthio-2,3-epithiopropane, 3-mercap
- polyvalent thiol (polythiol) compound examples include 1,1-methanedithiol, 1,2-ethanedithiol, 1,1-propanedithiol, 1,2-propanedithiol, 1,3-propanedithiol, 2,2 -Propanedithiol, 1,6-hexanedithiol, 1,2,3-propanetrithiol, 1,1-cyclohexanedithiol, 1,2-cyclohexanedithiol, 2,2-dimethylpropane-1,3-dithiol, 3, 4-dimethoxybutane-1,2-dithiol, 2-methylcyclohexane-2,3-dithiol, 1,1-bis (mercaptomethyl) cyclohexane, thiomalic acid bis (2-mercaptoethyl ester), 2,3-dimercapto- 1-propanol (2-mercaptoacetate), 2,3-dimercapto
- thiol compounds it is preferable to select an aliphatic thiol compound rather than an aromatic one in consideration of the optical properties of the obtained molded article, particularly the Abbe number. Further, in view of optical properties, particularly refractive index requirements, it is even more preferable to select a compound having a sulfur atom in addition to a thiol group such as a sulfide bond and / or a disulfide bond. In view of the heat resistance of the obtained molded article, it is particularly preferable to select one or more compounds having three or more thiol groups from the viewpoint of increasing the three-dimensional crosslinkability.
- Preferred thiol compounds from the above viewpoints are 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 4,8 or 4,7 or 5,7-dimercaptomethyl-1,11-dimercapto-3, 6,9-trithiaundecane, pentaerythritol tetrakis (2-mercaptoacetate), pentaerythritol tetrakis (3-mercaptopropionate), 2,5-bis (mercaptomethyl) -1,4-dithiane, bis (mercaptoethyl) ) Sulfide, 1,1,3,3-tetrakis (mercaptomethylthio) propane, 4,6-bis (mercaptomethylthio) -1,3-dithiane, 2- (2,2-bis (mercaptomethylthio) ethyl) -1 , 3-dithietane, one or more polythiols selected from these It can comprise compounds.
- the amount of the thiol compound contained in the polymerizable composition of the present invention is such that when the total amount of the alkyne compound and the thiol compound represented by the general formula (1) is 100 parts by weight, the amount of the thiol compound used is too small. In some cases, the effects of improving hue and improving mechanical strength are small and undesirable. In addition, when the total amount of the compound represented by the general formula (1) and the thiol compound is 100 parts by weight, if the amount of the thiol compound used is too large, a decrease in heat resistance may be extremely undesirable.
- the content of the thiol compound in the polymerizable composition of the present invention is 25 parts by weight or more and 75 parts by weight when the total of the alkyne compound and the thiol compound represented by the general formula (1) is 100 parts by weight. Part or less is preferred.
- the polymerizable composition of the present invention may further contain a known polymerization catalyst in order to adjust the polymerization rate, if necessary.
- a known polymerization catalyst include peroxides such as perbutyl O, perhexyl O, benzoyl peroxide, and hydrogen peroxide, and azide compounds such as azobisbutyronitrile. When these radical generators are used as a catalyst, the polymerization can proceed under mild conditions.
- resin modifiers e.g., resin modifiers, chain extenders, crosslinking agents, light stabilizers typified by HALS, UV absorbers typified by benzotriazole, and antioxidants typified by hindered phenols Agents, anti-coloring agents, dyes such as anthraquinone disperse dyes, bluing agents, fillers, external mold release agents such as silicones, or acidic phosphates, quaternary ammonium salts or quaternary phosphonium salts
- an internal mold release agent represented by a surfactant and an adhesion improver may be added.
- an internal mold release agent includes what shows the mold release effect among the above-mentioned various catalysts.
- the amount of each additive that can be added differs depending on the type, structure, and effect of each additive, and cannot be unconditionally limited, but is usually 0.001 weight relative to the total weight of the polymerizable composition. % To 10% by weight, preferably 0.01% to 5% by weight.
- the dye is preferably used in the range of 1 ppb to 100 ppm. By setting it within these ranges, it is possible to produce a molded product that is cured more favorably, and the resulting molded product may have further improved transparency and optical properties.
- Method for preparing polymerizable composition As a method for producing a polymerizable composition in the present invention, typically, the compound represented by the above general formula (1) and, if necessary, the above various other polymerizable compounds are used in combination, and further required. The method of mixing and dissolving after adding the said polymerization catalyst according to the above is mentioned.
- the obtained polymerizable composition is useful as a raw material monomer composition for a transparent molded article having an extremely high refractive index.
- the polymerizable composition of the present invention can be further purified as necessary.
- Purifying the polymerizable composition is a technique used for improving the transparency of a molded product obtained by curing, improving the hue, and increasing the purity.
- any known method such as recrystallization, column chromatography (silica gel method, activated carbon method, ion exchange resin method, etc.), extraction, etc. is performed at any timing.
- the transparency and hue of the molded product obtained by curing a composition obtained by purification generally may be improved.
- the method for washing the polymerizable composition is a method used to improve the transparency of the molded product obtained by curing or to improve the hue.
- a material that is washed with a polar and / or non-polar solvent at a later timing such as after removal and inhibits the transparency of the molded article for example, an inorganic material used in synthesizing a polymerizable composition or by-product
- a method of removing or reducing the salt, such as an ammonium salt may be mentioned.
- the solvent to be used cannot be generally limited by the polymerizable composition itself to be washed or the polarity of the solution containing the polymerizable composition, but the component to be removed can be dissolved and the polymerizable composition itself to be washed is used.
- those that are not compatible with the solution containing the polymerizable composition are preferable, and not only one type but also two or more types may be mixed and used.
- the components to be removed here vary depending on the purpose and application, but it is preferable to reduce them as much as possible. Usually, good results may be obtained when the content is 5000 ppm or less, more preferably 1000 ppm or less.
- the method of keeping, cooling, and filtering the polymerizable composition is a technique that is used to improve the transparency of the molded product obtained by curing or to improve the hue. Generally, it is performed at the time of taking out or after taking out after synthesis.
- a heat retention method for example, when the polymerizable composition is crystallized during storage and handling becomes worse, heating is performed in a range in which the performance of the polymerizable composition and the molded product obtained by curing the polymerizable composition does not deteriorate.
- a method of dissolving is mentioned.
- the temperature range to be heated and the method of heating and dissolving cannot be generally limited by the structure of the compound constituting the polymerizable composition to be handled, but are usually performed at a temperature within the freezing point + 50 ° C., preferably within + 20 ° C., Examples thereof include a method of mechanically stirring with a stirrable device or a method of moving and dissolving the internal solution by bubbling with an inert gas in the composition. Cooling is usually performed for the purpose of increasing the storage stability of the polymerizable composition. For example, when the melting point of the polymerizable composition is high, the storage temperature should be considered in order to improve the handling property after crystallization. .
- the cooling temperature cannot be unconditionally limited depending on the structure of the compound constituting the polymerizable composition to be handled and the storage stability, but it is usually necessary to store at or below the temperature at which the stability of the polymerizable composition of the present invention can be maintained. .
- the polymerizable composition of the present invention is a polymerizable composition used for optical applications, its extremely high transparency is required. Therefore, it is usually preferable to filter the polymerizable composition with a filter having a small pore size.
- the pore size of the filter used here is usually 0.05 ⁇ m or more and 10 ⁇ m or less. However, in consideration of operability and performance, it is preferably 0.05 ⁇ m or more and 5 ⁇ m or less, more preferably 0.1 ⁇ m or more and 5 ⁇ m or less. is there.
- the polymerizable composition of the present invention is no exception, and in many cases, good results can be obtained by filtration.
- the temperature at which filtration is performed a more preferable result may be obtained if it is performed at a low temperature near the freezing point.
- the reduced pressure treatment is a technique generally used for removing a solvent, dissolved gas, and odor that deteriorate the performance of a molded product obtained by curing the polymerizable composition. Since the dissolved solvent may cause a decrease in the refractive index and heat resistance of the generally obtained molded article, it is preferably removed as much as possible.
- the permissible value of the dissolved solvent cannot be generally limited depending on the structure of the compound constituting the polymerizable composition to be handled and the structure of the dissolved solvent, but is usually preferably 1% or less, more preferably 5000 ppm or less. . It is preferable to remove the dissolved gas from the viewpoint of suppressing the inhibition of the polymerization and the viewpoint of suppressing the mixing of bubbles in the obtained molded body.
- a gas such as water vapor by bubbling with a dry gas.
- a gas such as water vapor by bubbling with a dry gas.
- it can set according to the structure of the compound which comprises a polymeric composition, the physical property and structure of dissolved gas, and a kind.
- the obtained polymerizable composition is usually polymerized and cured in accordance with a method for polymerizing a known thietane group-containing compound, whereby a molded product can be obtained.
- the kind and amount of the polymerization catalyst and the like, and the kind and ratio of the monomer for obtaining a molded body made of the cured resin are set depending on the structure of the compound constituting the polymerizable composition.
- the molded object obtained by heat-hardening this polymeric composition can be used as an optical material.
- optical materials include eyeglass lenses for correcting vision, lenses for imaging equipment, Fresnel lenses for liquid crystal projectors, lenticular lenses, contact lenses, and other plastic lenses; sealing materials for light-emitting diodes (LEDs); optical waveguides; optical lenses And optical adhesives used for bonding optical waveguides; antireflection films used for optical lenses; and transparent coatings or transparent substrates used for liquid crystal display device members such as substrates, light guide plates, films, and sheets.
- the molding mold described above is composed of, for example, two molds that are mirror-polished through a gasket made of polyethylene, ethylene-vinyl acetate copolymer, polyvinyl chloride, or the like.
- the mold is typically a combination of glass and glass, and other molds include glass and plastic plate, glass and metal plate, but are not limited thereto.
- the molding mold may be a mold in which two molds are fixed with a tape such as a polyester adhesive tape. As needed, you may perform well-known processing methods, such as a mold release process, with respect to a casting_mold
- the polymerization temperature is influenced by the polymerization conditions such as the type of polymerization initiator and is not limited, but is usually ⁇ 50 ° C. or higher and 200 ° C. or lower, preferably ⁇ 20 ° C. It is 170 degreeC or less, More preferably, it is 0 degreeC or more and 150 degrees C or less.
- the polymerization time is affected by the polymerization temperature, but is usually 0.01 hours or more and 200 hours or less, preferably 0.05 hours or more and 100 hours or less. Moreover, it is also possible to carry out polymerization by combining several temperatures by performing constant temperature, temperature increase, temperature decrease or the like as necessary.
- the polymerizable composition of the present invention can also be polymerized by irradiating an active energy ray such as an electron beam, an ultraviolet ray or a visible ray.
- an active energy ray such as an electron beam, an ultraviolet ray or a visible ray.
- a radical polymerization catalyst or a cationic polymerization catalyst that initiates polymerization by active energy rays is used as necessary.
- the obtained molded body may be annealed as necessary after curing. If necessary, surface polishing, antistatic treatment, hard coat treatment, non-reflective coating treatment, dyeing treatment, dyeing treatment, antireflection, high hardness, wear resistance improvement, antifogging or fashionability.
- Various known physical or chemical treatments such as light treatment (for example, photochromic lens formation treatment) may be performed.
- a molded body made of a resin obtained by polymerizing the polymerizable composition of the present invention has a high refractive index, and further has high transparency, good heat resistance and mechanical strength. It is useful as an optical material such as a lens.
- the produced potassium bromide salt was removed by filtration, and the solvent was distilled off using a rotary evaporator.
- the obtained reaction product was dissolved in 125 g of dichloromethane and washed twice with 30 g of water.
- the organic layer was separated, dehydrated with sodium sulfate, and filtered to remove salts. Concentration under reduced pressure using a rotary evaporator gave 17.80 g (yield 80.9%, purity 89.2%) of the following compound (propargyl thioacetate).
- Liquid separation washing was performed with water, 5% HCl aqueous solution, water, 5% NaHCO 3 aqueous solution and water, and the organic layer was dehydrated with magnesium sulfate. After removing the salt by filtration, the solvent was distilled off with a rotary evaporator and then dried under reduced pressure with a vacuum pump to obtain 59.2 g (yield 80.3%) of the compound shown below.
- Example 1 Synthesis of bispropargylthiomethylene (compound represented by the following formula (1e)) Charged 37.8 g of propargyl bromide (0.25 mol: commercial product (manufactured by Tokyo Chemical Industry Co., Ltd.)) into a reactor equipped with a stirrer. Then, 115 ml of toluene was added and dissolved by stirring. Subsequently, after cooling to 10 ° C. using an ice water bath, 10.0 g (0.125 mol) of methanedithiol and 25.3 g of triethylamine (0.25 mol: commercially available product (manufactured by Wako Pure Chemical Industries, Ltd.)) were charged. Stir at room temperature.
- Example 2 Synthesis of bispropargyl thiocarbonate (compound represented by the following formula (1f)) A reactor equipped with a stirrer was charged with 9.9 g of triphosgene (0.033 mol: a commercial product (manufactured by Tokyo Chemical Industry Co., Ltd.)), 70 ml of methylene chloride was added and dissolved by stirring. Subsequently, after cooling to 10 ° C. using an ice water bath, 11.0 g (0.017 mol) of propargyl thiol (produced by the method of Reference Production Example 2) and 13.2 g (0.017 mol) of pyridine were added to 70 ml of methylene chloride.
- the dissolved solution was added dropwise over 1 hour, stirred for an additional 1.5 hours, and then stirred at room temperature for 1.5 hours.
- the reaction was stopped with a saturated aqueous NaHCO 3 solution, washed with water, 5% HCl aqueous solution, water, 5% NaHCO 3 aqueous solution and water, and the organic layer was dehydrated with magnesium sulfate.
- the solvent was distilled off with a rotary evaporator and then dried under reduced pressure with a vacuum pump to obtain 3.8 g (yield 53.4%) of the compound shown below.
- Example 3 Synthesis of bispropargyl thiocarbamate (compound represented by the following formula (1 g))
- a propargyl thiol toluene solution produced by the method of Reference Production Example 2
- 24.3 g 0.05 Mol
- 10 ml of toluene was added and stirred.
- 4.1 g (0.05 mol) of propargyl isocyanate was inserted, and the mixture was stirred at room temperature for 2 days.
- Example 18 At room temperature (25 ° C.), 0.67 g of the compound of the formula (1h) produced in Example 4 was weighed in a glass beaker, and then 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane 52 g was weighed. Heat to 80 ° C. to dissolve. After cooling to 70 ° C., 1 mg (0.1 part by weight: commercially available product (manufactured by Nippon Oil & Fats)) of 2-ethylhexanoate as a polymerization catalyst is added and degassed under reduced pressure, and a glass mold and tape are used The polymerizable compound was injected into the casting mold. Polymerization was carried out in a heating oven at 90 ° C. for 16 hours and at 100 ° C. for 3 hours. The appearance of the obtained resin molding was transparent, and the refractive index ne was 1.795.
- Example 5 a resin molded product was produced in the same manner as in Example 5 except that the compound produced in Reference Production Example 3 or 4 was used.
- the appearance of any of the obtained resin moldings was transparent and had a refractive index of about 1.7 to 1.8.
- a polymerizable composition comprising the sulfur-containing alkyne compound according to [a1].
- the thiol compound is 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 4,8 or 4,7 or 5,7-dimercaptomethyl-1,11-dimercapto-3,6 , 9-trithiaundecane, pentaerythritol tetrakis (2-mercaptoacetate), pentaerythritol tetrakis (3-mercaptopropionate), 2,5-bis (mercaptomethyl) -1,4-dithiane, bis (mercaptoethyl) Sulfide, 1,1,3,3-tetrakis (mercaptomethylthio) propane, 4,6-bis (mercaptomethylthio) -1,3-dithiane, 2- (2,2-bis (mercaptomethylthio) ethyl) -1,
- [A5] A molded product obtained by curing the polymerizable composition according to any one of [a2] to [a4].
- [A6] An optical material comprising the molded article according to [a5].
- [A7] A plastic lens comprising the molded product according to [a5].
- the present invention further includes the following aspects.
- [B1] A novel antimony-containing compound represented by the following formula (1h).
- [B2] A polymerizable composition comprising the antimony-containing compound according to [b1].
- [B3] The polymerizable composition according to [b2], further including a thiol compound.
- the thiol compound is 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 4,8 or 4,7 or 5,7-dimercaptomethyl-1,11-dimercapto-3,6 , 9-trithiaundecane, pentaerythritol tetrakismercaptoacetate, pentaerythritol tetrakismercaptopropionate, 2,5-bis (mercaptomethyl) -1,4-dithiane, bis (mercaptoethyl) sulfide, 1,1,3 One selected from 3-tetrakis (mercaptomethylthio) propane, 4,6-bis (mercaptomethylthio) -1,3-dithiane, 2- (2,2-bis (mercaptomethylthio) ethyl) -1,3-dithietane
- the polymerizable composition according to [b3] comprising the above polythiol compound.
- [B5] A molded product obtained by curing the polymerizable composition according to any one of [b2] to [b4].
- [B6] An optical material comprising the molded article according to [b5].
- [B7] A plastic lens comprising the molded product according to [b5].
- [B8] A method for producing an antimony-containing compound represented by the following formula (1h), wherein an antimony halide is allowed to act on a propargyl thioacetylated product or propargylthiol in the presence of a solvent and a base inert to the reaction.
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Abstract
Description
このような樹脂に関する従来の技術として、ジスルフィド結合を有する化合物を用いた例が特許文献1に記載されている。また、非特許文献1には光学物性は不明であるが、硫黄と3重結合を有する化合物とポリチオールを共重合することで樹脂が得られるという記載がある。
なお、特許文献6、非特許文献2~5には、両末端に3重結合を有する化合物が開示されている。
[1] 下記一般式(1)で表されるアルキン化合物を含む重合性組成物;
[2] 下記一般式(2)または(3)で表されるアルキン化合物を含む、[1]に記載の重合性組成物;
[3] 炭素原子の1つがアンチモン原子で置き換えられた前記チオフェニレン基は、下記式(4)で表される2価の基である、[1]または[2]に記載の重合性組成物;
[4] さらに、チオール化合物を含む[1]~[3]のいずれかに記載の重合性組成物。
[5] 前記チオール化合物は、4-メルカプトメチル-1,8-ジメルカプト-3,6-ジチアオクタン、4,8または4,7または5,7-ジメルカプトメチル-1,11-ジメルカプト-3,6,9-トリチアウンデカン、ペンタエリスリトールテトラキス(2-メルカプトアセテート)、ペンタエリスリトールテトラキス(3-メルカプトプロピオネート)、2,5-ビス(メルカプトメチル)-1,4-ジチアン、ビス(メルカプトエチル)スルフィド、1,1,3,3-テトラキス(メルカプトメチルチオ)プロパン、4,6-ビス(メルカプトメチルチオ)-1,3-ジチアン、2-(2,2-ビス(メルカプトメチルチオ)エチル)-1,3-ジチエタンから選ばれる1種以上のポリチオール化合物を含む、[4]に記載の重合性組成物。
[6] [1]~[5]のいずれかに記載の重合性組成物を硬化させた成形体。
[7] [6]に記載の成形体からなる光学材料。
[8] [6]に記載の成形体からなるプラスチックレンズ。
[9] 下記一般式(5)で表されるアルキン化合物;
[10] 炭素原子の1つがアンチモン原子で置き換えられた前記チオフェニレン基は、下記式(4)で表される基である、[9]に記載のアルキン化合物;
[重合性組成物]
本発明に係る重合性組成物は、下記一般式(1)で表されるアルキン化合物を含む。
「炭素原子の1つがアンチモン原子で置き換えられたチオフェニレン基」において、アンチモン原子の位置は特に限定されない。本発明の効果の観点から下記一般式(4)で表す基を用いることができる。
一般式(1)中、R1およびR2は炭素数1~2のアルキレン基を表し、それぞれ同一でも異なっていてもよい。R1およびR2は炭素数1のアルキレン基であることが好ましい。
m、nはそれぞれ0または1を表す。
このようなアルキン化合物を含む重合性組成物によれば、高屈折率である透明な光学材料を得ることができる。
これらの化合物は、以下のようにして得ることができる。
一般式(1-1)で表される化合物は以下のようにして得ることができる。
反応を実施するに際し、反応を効率よく行うために、生成するハロゲン化水素の捕捉剤として塩基性化合物を用いることが好ましい。
かかる塩基性化合物として、たとえば、水酸化ナトリウム、水酸化カリウム、水酸化リチウム、炭酸ナトリウム、炭酸カリウム、炭酸リチウム、重炭酸ナトリウム、重炭酸カリウム、重炭酸リチウム、水酸化マグネシウム、水酸化カルシウムなどの無機塩基;および
ピリジン、トリエチルアミン、ジメチルアニリン、ジエチルアニリン、1,8-ジアザビシクロ[5.4.0]-7-ウンデセンなどの有機塩基が例示される。
一般式(1-2)で表される化合物は以下のようにして得ることができる。
一般式(1-3)で表される化合物は以下のようにして得ることができる。
上記に示した化合物の反応温度は、特に制限するものではないが、通常、-78℃以上200℃以下の範囲であり、好ましくは、-78℃以上100℃以下である。
一般式(1-4)で表される化合物は以下のようにして得ることができる。
上記反応において使用することができる溶媒としては、反応に不活性な溶媒であれば特に限定するものではなく、石油エーテル、ヘキサン、ベンゼン、トルエン、キシレン、メシチレンなどの炭化水素系溶媒;
ジエチルエーテル、テトラヒドロフラン、ジエチレングリコールジメチルエーテルなどのエーテル系溶媒;
アセトン、メチルエチルケトン、メチルイソブチルケトンなどのケトン系溶媒;
酢酸エチル、酢酸ブチル、酢酸アミルなどのエステル系溶媒;
塩化メチレン、クロロホルム、クロルベンゼン、ジクロルベンゼンなどの含塩素系溶媒;
などが例示される。
ナトリウムメトキシド、ナトリウムエトキシド、カリウムt-ブトキシドなどのアルカリ金属アルコキシド;および
ピリジン、トリエチルアミン、ジメチルアニリン、ジエチルアニリン、1,8-ジアザビシクロ[5.4.0]-7-ウンデセンなどの有機塩基;などが挙げられる。
また、反応時間は反応温度により影響されるが、通常、数分から100時間である。
一般式(1-5)で表される化合物は、例えば、プロピンまたは1-ブチンのチオアセチル化物、プロパルギルチオールまたは3-ブチン-1-チオールに、反応に不活性な溶媒および塩基の存在下で、アンチモンハライドを作用させることで得ることができる。
ジエチルエーテル、テトラヒドロフラン、ジエチレングリコールジメチルエーテルなどのエーテル系溶媒;
アセトン、メチルエチルケトン、メチルイソブチルケトンなどのケトン系溶媒;
酢酸エチル、酢酸ブチル、酢酸アミルなどのエステル系溶媒;
塩化メチレン、クロロホルム、クロルベンゼン、ジクロルベンゼンなどの含塩素系溶媒;
N,N-ジメチルホルムアミド、N,N-ジメチルアセトアミド、N,N-ジメチルイミダゾリジノン、ジメチルスルホキシドなどの非プロトン性極性溶媒;
テトラヒドロチオフェン、チオフェン、スルホラン、トリメチレンスルフィド、ジエチルスルフィド、ジ-n-プロピルスルフィド、ジ-t-ブチルスルフィド、3-メルカプトチエタン、ビス(2-メルカプトエチル)スルフィドなどの含硫系溶媒;
メタノール、エタノール、プロパノール、イソプロパノール、ブタノール、t-ブタノールなどの脂肪族アルコール;および
水などが例示される。
ナトリウムメトキシド、ナトリウムエトキシド、カリウムt-ブトキシドなどのアルカリ金属アルコキシド;および
ピリジン、トリエチルアミン、ジメチルアニリン、ジエチルアニリン、1,8-ジアザビシクロ[5.4.0]-7-ウンデセンなどの有機塩基;などが挙げられる。
また、反応時間は反応温度により影響されるが、通常、数分から100時間である。
さらに、このアルキン化合物とともにチオール化合物を含有させることができ、光学材料用重合性組成物として好適に用いることができる。
1,2-ジメルカプトベンゼン、1,3-ジメルカプトベンゼン、1,4-ジメルカプトベンゼン、1,2-ビス(メルカプトメチル)ベンゼン、1,3-ビス(メルカプトメチル)ベンゼン、1,4-ビス(メルカプトメチル)ベンゼン、1,2-ビス(メルカプトエチル)ベンゼン、1,3-ビス(メルカプトエチル)ベンゼン、1,4-ビス(メルカプトエチル)ベンゼン、1,2,3-トリメルカプトベンゼン、1,2,4-トリメルカプトベンゼン、1,3,5-トリメルカプトベンゼン、1,2,3-トリス(メルカプトメチル)ベンゼン、1,2,4-トリス(メルカプトメチル)ベンゼン、1,3,5-トリス(メルカプトメチル)ベンゼン、1,2,3-トリス(メルカプトエチル)ベンゼン、1,2,4-トリス(メルカプトエチル)ベンゼン、1,3,5-トリス(メルカプトエチル)ベンゼン、2,5-トルエンジチオール、3,4-トルエンジチオール、1,3-ジ(p-メトキシフェニル)プロパン-2,2-ジチオール、1,3-ジフェニルプロパン-2,2-ジチオール、フェニルメタン-1,1-ジチオール、2,4-ジ(p-メルカプトフェニル)ペンタン等の芳香族ポリチオール化合物;
1,2-ビス(メルカプトエチルチオ)ベンゼン、1,3-ビス(メルカプトエチルチオ)ベンゼン、1,4-ビス(メルカプトエチルチオ)ベンゼン、1,2,3-トリス(メルカプトメチルチオ)ベンゼン、1,2,4-トリス(メルカプトメチルチオ)ベンゼン、1,3,5-トリス(メルカプトメチルチオ)ベンゼン、1,2,3-トリス(メルカプトエチルチオ)ベンゼン、1,2,4-トリス(メルカプトエチルチオ)ベンゼン、1,3,5-トリス(メルカプトエチルチオ)ベンゼン等、およびこれらの核アルキル化物等のメルカプト基以外に硫黄原子を含有する芳香族ポリチオール化合物;
ビス(メルカプトメチル)スルフィド、ビス(メルカプトメチル)ジスルフィド、ビス(メルカプトエチル)スルフィド、ビス(メルカプトエチル)ジスルフィド、ビス(メルカプトプロピル)スルフィド、ビス(メルカプトメチルチオ)メタン、ビス(2-メルカプトエチルチオ)メタン、ビス(3-メルカプトプロピルチオ)メタン、1,2-ビス(メルカプトメチルチオ)エタン、1,2-ビス(2-メルカプトエチルチオ)エタン、1,2-ビス(3-メルカプトプロピル)エタン、1,3-ビス(メルカプトメチルチオ)プロパン、1,3-ビス(2-メルカプトエチルチオ)プロパン、1,3-ビス(3-メルカプトプロピルチオ)プロパン、1,2,3-トリス(メルカプトメチルチオ)プロパン、1,2,3-トリス(2-メルカプトエチルチオ)プロパン、1,2,3-トリス(3-メルカプトプロピルチオ)プロパン、1,2-ビス[(2-メルカプトエチル)チオ]-3-メルカプトプロパン、4,8-ジメルカプトメチル-1,11-ジメルカプト-3,6,9-トリチアウンデカン、4,7-ジメルカプトメチル-1,11-ジメルカプト-3,6,9-トリチアウンデカン、5,7-ジメルカプトメチル-1,11-ジメルカプト-3,6,9-トリチアウンデカン、テトラキス(メルカプトメチルチオメチル)メタン、テトラキス(2-メルカプトエチルチオメチル)メタン、テトラキス(3-メルカプトプロピルチオメチル)メタン、ビス(2,3-ジメルカプトプロピル)スルフィド、ビス(1,3-ジメルカプトプロピル)スルフィド、2,5-ジメルカプト-1,4-ジチアン、2,5-ビス(メルカプトメチル)-1,4-ジチアン、2,5-ジメルカプトメチル-2,5-ジメチル-1,4-ジチアン、ビス(メルカプトメチル)ジスルフィド、ビス(メルカプトエチル)ジスルフィド、ビス(メルカプトプロピル)ジスルフィド、4-メルカプトメチル-1,8-ジメルカプト-3,6-ジチアオクタン等のメルカプト基以外に硫黄原子を含有する脂肪族ポリチオール化合物、ならびにこれらのチオグリコール酸およびメルカプトプロピオン酸のエステル;
ヒドロキシメチルスルフィドビス(2-メルカプトアセテート)、ヒドロキシメチルスルフィドビス(3-メルカプトプロピオネート)、ヒドロキシエチルスルフィドビス(2-メルカプトアセテート)、ヒドロキシエチルスルフィドビス(3-メルカプトプロピオネート)、ヒドロキシプロピルスルフィドビス(2-メルカプトアセテート)、ヒドロキシプロピルスルフィドビス(3-メルカプトプロピオネート)、ヒドロキシメチルジスルフィドビス(2-メルカプトアセテート)、ヒドロキシメチルジスルフィドビス(3-メルカプトプロピオネート)、ヒドロキシエチルジスルフィドビス(2-メルカプトアセテート)、ヒドロキシエチルジスルフィドビス(3-メルカプトプロピオネート)、ヒドロキシプロピルジスルフィドビス(2-メルカプトアセテート)、ヒドロキシプロピルジスルフィドビス(3-メルカプトプロピオネート)、2-メルカプトエチルエーテルビス(2-メルカプトアセテート)、2-メルカプトエチルエーテルビス(3-メルカプトプロピオネート)、1,4-ジチアン-2,5-ジオールビス(2-メルカプトアセテート)、1,4-ジチアン-2,5-ジオールビス(3-メルカプトプロピオネート)、チオジグリコール酸ビス(2-メルカプトエチルエステル)、チオジプロピオン酸ビス(2-メルカプトエチルエステル)、4,4-チオジブチル酸ビス(2-メルカプトエチルエステル)、ジチオジグリコール酸ビス(2-メルカプトエチルエステル)、ジチオジプロピオン酸ビス(2-メルカプトエチルエステル)、4,4-ジチオジブチル酸ビス(2-メルカプトエチルエステル)、チオジグリコール酸ビス(2,3-ジメルカプトプロピルエステル)、チオジプロピオン酸ビス(2,3-ジメルカプトプロピルエステル)、ジチオグリコール酸ビス(2,3-ジメルカプトプロピルエステル)、ジチオジプロピオン酸ビス(2,3-ジメルカプトプロピルエステル)等のメルカプト基以外に硫黄原子とエステル結合を含有する脂肪族ポリチオール化合物;
3,4-チオフェンジチオール、2,5-ジメルカプト-1,3,4-チアジアゾール等のメルカプト基以外に硫黄原子を含有する複素環化合物;
グリセリンジ(メルカプトアセテート)、1-ヒドロキシ-4-メルカプトシクロヘキサン、2,4-ジメルカプトフェノール、2-メルカプトハイドロキノン、4-メルカプトフェノール、3,4-ジメルカプト-2-プロパノール、1,3-ジメルカプト-2-プロパノール、2,3-ジメルカプト-1-プロパノール、1,2-ジメルカプト-1,3-ブタンジオール、ペンタエリスリトールトリス(3-メルカプトプロピオネート)、ペンタエリスリトールモノ(3-メルカプトプロピオネート)、ペンタエリスリトールビス(3-メルカプトプロピオネート)、ペンタエリスリトールトリス(チオグリコレート)、ジペンタエリスリトールペンタキス(3-メルカプトプロピオネート)、ヒドロキシメチル-トリス(メルカプトエチルチオメチル)メタン、1-ヒドロキシエチルチオ-3-メルカプトエチルチオベンゼン等のメルカプト基以外にヒドロキシ基を含有する化合物;
1,1,3,3-テトラキス(メルカプトメチルチオ)プロパン、4,6-ビス(メルカプトメチルチオ)-1,3-ジチアン、2-(2,2-ビス(メルカプトメチルチオ)エチル)-1,3-ジチエタン、1,1,2,2-テトラキス(メルカプトメチルチオ)エタン、1,1,5,5-テトラキス(メルカプトメチルチオ)-3-チアペンタン、1,1,6,6-テトラキス(メルカプトメチルチオ)-3,4-ジチアヘキサン、2,2-ビス(メルカプトメチルチオ)エタンチオール、2-(4,5-ジメルカプト-2-チアペンチル)-1,3-ジチアシクロペンタン、2,2-ビス(メルカプトメチル)-1,3-ジチアシクロペンタン、2,5-ビス(4,4-ビス(メルカプトメチルチオ)-2-チアブチル)-1,4-ジチアン、2,2-ビス(メルカプトメチルチオ)-1,3-プロパンジチオール、3-メルカプトメチルチオ-1,7-ジメルカプト-2,6-ジチアヘプタン、3,6-ビス(メルカプトメチルチオ)-1,9-ジメルカプト-2,5,8-トリチアノナン、4,6-ビス(メルカプトメチルチオ)-1,9-ジメルカプト-2,5,8-トリチアノナン、3-メルカプトメチルチオ-1,6-ジメルカプト-2,5-ジチアヘキサン、1,1,9,9-テトラキス(メルカプトメチルチオ)-5-(3,3-ビス(メルカプトメチルチオ)-1-チアプロピル)3,7-ジチアノナン、トリス(2,2-ビス(メルカプトメチルチオ)エチル)メタン、トリス(4,4-ビス(メルカプトメチルチオ)-2-チアブチル)メタン、テトラキス(2,2-ビス(メルカプトメチルチオ)エチル)メタン、テトラキス(4,4-ビス(メルカプトメチルチオ)-2-チアブチル)メタン、3,5,9,11-テトラキス(メルカプトメチルチオ)-1,13-ジメルカプト-2,6,8,12-テトラチアトリデカン、3,5,9,11,15,17-ヘキサキス(メルカプトメチルチオ)-1,19-ジメルカプト-2,6,8,12,14,18-ヘキサチアノナデカン、9-(2,2-ビス(メルカプトメチルチオ)エチル)-3,5,13,15-テトラキス(メルカプトメチルチオ)-1,17-ジメルカプト-2,6,8,10,12,16-ヘキサチアヘプタデカン、3,4,8,9-テトラキス(メルカプトメチルチオ)-1,11-ジメルカプト-2,5,7,10-テトラチアウンデカン、3,4,8,9,13,14-ヘキサキス(メルカプトメチルチオ)-1,16-ジメルカプト-2,5,7,10,12,15-ヘキサチアヘキサデカン、8-{ビス(メルカプトメチルチオ)メチル}-3,4,12,13-テトラキス(メルカプトメチルチオ)-1,15-ジメルカプト-2,5,7,9,11,14-ヘキサチアペンタデカン、4,6-ビス{3,5-ビス(メルカプトメチルチオ)-7-メルカプト-2,6-ジチアヘプチルチオ}-1,3-ジチアン、4-{3,5-ビス(メルカプトメチルチオ)-7-メルカプト-2,6-ジチアヘプチルチオ}-6-メルカプトメチルチオ-1,3-ジチアン、1,1-ビス{4-(6-メルカプトメチルチオ)-1,3-ジチアニルチオ}-3,3-ビス(メルカプトメチルチオ)プロパン、1,3-ビス{4-(6-メルカプトメチルチオ)-1,3-ジチアニルチオ}-1,3-ビス(メルカプトメチルチオ)プロパン、1-{4-(6-メルカプトメチルチオ)-1,3-ジチアニルチオ}-3-{2,2-ビス(メルカプトメチルチオ)エチル}-7,9-ビス(メルカプトメチルチオ)-2,4,6,10-テトラチアウンデカン、1-{4-(6-メルカプトメチルチオ)-1,3-ジチアニルチオ}-3-{2-(1,3-ジチエタニル)}メチル-7,9-ビス(メルカプトメチルチオ)-2,4,6,10-テトラチアウンデカン、1,5-ビス{4-(6-メルカプトメチルチオ)-1,3-ジチアニルチオ}-3-{2-(1,3-ジチエタニル)}メチル-2,4-ジチアペンタン、4,6-ビス[3-{2-(1,3-ジチエタニル)}メチル-5-メルカプト-2,4-ジチアペンチルチオ]-1,3-ジチアン、4,6-ビス{4-(6-メルカプトメチルチオ)-1,3-ジチアニルチオ}-1,3-ジチアン、4-{4-(6-メルカプトメチルチオ)-1,3-ジチアニルチオ}-6-{4-(6-メルカプトメチルチオ)-1,3-ジチアニルチオ}-1,3-ジチアン、3-{2-(1,3-ジチエタニル)}メチル-7,9-ビス(メルカプトメチルチオ)-1,11-ジメルカプト-2,4,6,10-テトラチアウンデカン、9-{2-(1,3-ジチエタニル)}メチル-3,5,13,15-テトラキス(メルカプトメチルチオ)-1,17-ジメルカプト-2,6,8,10,12,16-ヘキサチアヘプタデカン、3-{2-(1,3-ジチエタニル)}メチル-7,9,13,15-テトラキス(メルカプトメチルチオ)-1,17-ジメルカプト-2,4,6,10,12,16-ヘキサチアヘプタデカン、3,7-ビス{2-(1,3-ジチエタニル)}メチル-1,9-ジメルカプト-2,4,6,8-テトラチアノナン、4-{3,4,8,9-テトラキス(メルカプトメチルチオ)-11-メルカプト-2,5,7,10-テトラチアウンデシル}-5-メルカプトメチルチオ-1,3-ジチオラン、4,5-ビス{3,4-ビス(メルカプトメチルチオ)-6-メルカプト-2,5-ジチアヘキシルチオ}-1,3-ジチオラン、4-{3,4-ビス(メルカプトメチルチオ)-6-メルカプト-2,5-ジチアヘキシルチオ}-5-メルカプトメチルチオ-1,3-ジチオラン、4-{3-ビス(メルカプトメチルチオ)メチル-5,6-ビス(メルカプトメチルチオ)-8-メルカプト-2,4,7-トリチアオクチル}-5-メルカプトメチルチオ-1,3-ジチオラン、2-[ビス{3,4-ビス(メルカプトメチルチオ)-6-メルカプト-2,5-ジチアヘキシルチオ}メチル]-1,3-ジチエタン、2-{3,4-ビス(メルカプトメチルチオ)-6-メルカプト-2,5-ジチアヘキシルチオ}メルカプトメチルチオメチル-1,3-ジチエタン、2-{3,4,8,9-テトラキス(メルカプトメチルチオ)-11-メルカプト-2,5,7,10-テトラチアウンデシルチオ}メルカプトメチルチオメチル-1,3-ジチエタン、2-{3-ビス(メルカプトメチルチオ)メチル-5,6-ビス(メルカプトメチルチオ)-8-メルカプト-2,4,7-トリチアオクチル}メルカプトメチルチオメチル-1,3-ジチエタン、4,5-ビス[1-{2-(1,3-ジチエタニル)}-3-メルカプト-2-チアプロピルチオ]-1,3-ジチオラン、4-[1-{2-(1,3-ジチエタニル)}-3-メルカプト-2-チアプロピルチオ]-5-{1,2-ビス(メルカプトメチルチオ)-4-メルカプト-3-チアブチルチオ}-1,3-ジチオラン、2-[ビス{4-(5-メルカプトメチルチオ-1,3-ジチオラニル)チオ}]メチル-1、3-ジチエタン、4-{4-(5-メルカプトメチルチオ-1,3-ジチオラニル)チオ}-5-[1-{2-(1,3-ジチエタニル)}-3-メルカプト-2-チアプロピルチオ]-1,3-ジチオラン、さらにこれらのオリゴマー等のジチオアセタールもしくはジチオケタール骨格を有する化合物;
トリス(メルカプトメチルチオ)メタン、トリス(メルカプトエチルチオ)メタン、1,1,5,5-テトラキス(メルカプトメチルチオ)-2,4-ジチアペンタン、ビス[4,4-ビス(メルカプトメチルチオ)-1,3-ジチアブチル](メルカプトメチルチオ)メタン、トリス[4,4-ビス(メルカプトメチルチオ)-1,3-ジチアブチル]メタン、2,4,6-トリス(メルカプトメチルチオ)-1,3,5-トリチアシクロヘキサン、2,4-ビス(メルカプトメチルチオ)-1,3,5-トリチアシクロヘキサン、1,1,3,3-テトラキス(メルカプトメチルチオ)-2-チアプロパン、ビス(メルカプトメチル)メチルチオ-1,3,5-トリチアシクロヘキサン、トリス[(4-メルカプトメチル-2,5-ジチアシクロヘキシル-1-イル)メチルチオ]メタン、2,4-ビス(メルカプトメチルチオ)-1,3-ジチアシクロペンタン、2-メルカプトエチルチオ-4-メルカプトメチル-1,3-ジチアシクロペンタン、2-(2,3-ジメルカプトプロピルチオ)-1,3-ジチアシクロペンタン、4-メルカプトメチル-2-(2,3-ジメルカプトプロピルチオ)-1,3-ジチアシクロペンタン、4-メルカプトメチル-2-(1,3-ジメルカプト-2-プロピルチオ)-1,3-ジチアシクロペンタン、トリス[2,2-ビス(メルカプトメチルチオ)-1-チアエチル]メタン、トリス[3,3-ビス(メルカプトメチルチオ)-2-チアプロピル]メタン、トリス[4,4-ビス(メルカプトメチルチオ)-3-チアブチル]メタン、2,4,6-トリス[3,3-ビス(メルカプトメチルチオ)-2-チアプロピル]-1,3,5-トリチアシクロヘキサン、テトラキス[3,3-ビス(メルカプトメチルチオ)-2-チアプロピル]メタン等、さらにこれらのオリゴマー等のオルトトリチオ蟻酸エステル骨格を有する化合物;
3,3'-ジ(メルカプトメチルチオ)-1,5-ジメルカプト-2,4-ジチアペンタン、2,2'-ジ(メルカプトメチルチオ)-1,3-ジチアシクロペンタン、2,7-ジ(メルカプトメチル)-1,4,5,9-テトラチアスピロ[4.4]ノナン、3,9-ジメルカプト-1,5,7,11-テトラチアスピロ[5.5]ウンデカン、さらにこれらのオリゴマー等のオルトテトラチオ炭酸エステル骨格を有する化合物等が挙げられるが、これらの例示化合物のみに限定されるものではない。これら例示化合物は、単独でも2種類以上混合して使用してもよい。
本発明の重合性組成物は、必要に応じて、重合速度を調整するため公知の重合触媒をさらに含んでいてもよい。重合触媒の例としてはパーブチルOやパーヘキシルO、過酸化ベンゾイル、過酸化水素水などの過酸化物やアゾビスブチロニトリルなどのアジド化合物があげられる。これらのラジカル発生剤を触媒として用いると温和な条件で重合を進行させることができる。
本発明における重合性組成物の製造方法として、代表的には、上記一般式(1)に示した化合物と、必要に応じて上記の他の各種重合性化合物とを併用して、さらに必要に応じて上記重合触媒を添加した後、混合、溶解させる方法などが挙げられる。
得られた重合性組成物は、極めて高い屈折率を有する透明な成形体用の原料モノマー組成物として有用である。
重合性組成物を精製するのは、硬化して得られる成形体の透明性を改良したり、色相を改良するためや純度を上げるために用いられる手法である。本発明の重合性組成物を精製する際には、公知の方法、たとえば、再結晶、カラムクロマト法(シリカゲル法や活性炭法、イオン交換樹脂法など)、抽出などのいかなる手法をいかなるタイミングで行ってもよく、一般に精製して得られる組成物を硬化させて得られる成形体の透明性や色相が改良されていればよい。
得られた重合性組成物は、通常、公知のチエタン基含有化合物を重合する際の方法に準じて重合し、硬化させることにより、成形体を得ることができる。なお、硬化樹脂からなる成形体を得るための重合触媒等の種類や量、単量体の種類や割合は、重合性組成物を構成する化合物の構造により設定される。
光学材料としては、たとえば、視力矯正用眼鏡レンズ、撮像機器用レンズ、液晶プロジェクター用フレネルレンズ、レンチキュラーレンズ、コンタクトレンズなどの各種プラスチックレンズ;発光ダイオード(LED)用封止材;光導波路;光学レンズや光導波路の接合に用いる光学用接着剤;光学レンズなどに用いる反射防止膜;基板、導光板、フィルム、シートなどの液晶表示装置部材に用いる透明性コーティングまたは透明性基板などが挙げられる。
プラスチックレンズの製造方法としては、公知の各種成形方法が挙げられるが、代表的には、注型重合が挙げられる。
(評価方法)
実施例で得られた成形体の物性評価を下記の方法により行った。
外観:目視により透明性を確認した。
屈折率:プルフリッヒ屈折計を用いて20℃で測定した。
なお、実施例で用いた1,1,3,3-テトラキス(メルカプトメチルチオ)プロパンを主成分とする混合物は、特開2001-342172号公報に記載の方法で製造した。
チオ酢酸プロパルギル(下記式で表される化合物)を合成した。
攪拌装置付きの反応器にチオ酢酸カリウム20.0g(0.175モル:市販品(東京化成工業社製))を装入し、メタノール60gを加えて攪拌溶解した。続けて氷水浴を用いて5℃まで冷却し、プロパルギルブロマイド20.4g(0.172モル:市販品(東京化成工業社製))を1時間かけて滴下装入し、4時間攪拌を続けた。生成した臭化カリウムの塩をろ過して除去し、ロータリーエバポレーターを用いて溶媒を留去した。得られた反応物を125gのジクロロメタンに溶解し、30gの水で二回洗浄をおこなった。有機層を分液して硫酸ナトリウムで脱水し、ろ過して塩類を除去した。ロータリーエバポレーターで減圧濃縮して下記に示される化合物(チオ酢酸プロパルギル)17.80g(収率80.9%、純度89.2%)を得た。
1H-NMR(溶媒:CDCl3、内部標準物質:TMS)δ:2.20(1H)、2.37(3H)、3.65(2H).
EI-MS 実測値[M]+:114、理論値[M]+:114
プロパルギルジスルフィド(下記式(1a)で表される化合物)の合成
攪拌装置付きの反応器に参考製造例1で合成したチオ酢酸プロパルギル6.0g(0.044モル)を装入し、水54gに加えて撹拌溶解した。続けて氷水浴を用いて10℃まで冷却した後に50%水酸化ナトリウム溶液10.6g(0.132モル:市販品(和光純薬社製))を装入し、プロパルギルチオールを合成した。次に0.5mol/Lヨウ素溶液40ml(0.02モル:市販品(和光純薬社製))を20分かけて滴下装入した。装入後、50gのジクロロメタンを加えて抽出し、50gの水で洗浄して塩を除去した後に分液した。5%チオ硫酸ナトリウム水溶液50gで洗浄分液後、飽和食塩水50gで洗浄分液をおこなった。有機層は硫酸マグネシウムで脱水し、ろ過して塩を除去した後に氷水浴で冷却しながらロータリーエバポレーターで溶媒を留去した。残った薄黄色液体を氷水浴で冷却しながら真空ポンプで減圧乾燥して下記に示される化合物2.27g(収率79.8%)を得た。
1H-NMR(溶媒:CDCl3、内部標準物質:TMS)δ:2.33(2H)、3.62(4H).
EI-MS 実測値[M-H]+:141、理論値[M]+:142
ビスプロパルギルチオエチレン(下記式(1b)で表される化合物)の合成
攪拌装置付きの反応器にエタンジチオール6.5g(0.069モル:市販品(東京化成工業社製))を装入し、メタノール80mlを加えて撹拌溶解した。続けて氷水浴を用いて10℃まで冷却した後に水酸化ナトリウム5.5g(0.139mol)を20mlの水に溶解した溶液を装入し、攪拌した。さらに0℃まで冷却した後に臭化プロパルギル16.5g(0.139mol:市販品(東京化成工業社製))を滴下装入し、室温で一晩静置した。析出した固体をろ取して水洗した後に、真空ポンプで減圧乾燥して下記に示される化合物10.0g(収率85%)を得た。
1H-NMR(溶媒:CDCl3、内部標準物質:TMS)δ:2.28(2H)、2.98(4H)、3.32(4H).
IR(ユニバーサルATR法)3251、2109、1417、1203、1172、1128、727、716、681、652、468cm-1.
ビスプロパルギルスルフィド(下記式(1c)で表される化合物)の合成
攪拌装置付きの反応器に純度46.2%の硫化ナトリウム3.5g(0.021モル:市販品(三協化成社製))を装入し、ジメチルホルムアミド12mlを加えて撹拌溶解した。続けて氷水浴を用いて10℃まで冷却した後にプロパルギルブロマイド5.0g(0.042モル:市販品(東京化成工業社製))を装入し、室温で一晩静置した。100mlの水に排出し、30mlの酢酸エチルで抽出、水50mlの水で3回洗浄、分液した。有機層を硫酸ナトリウムで乾燥し、ろ過して塩を除去した後に真空ポンプで減圧乾燥して下記に示される化合物1.7g(収率73%)を得た。
1H-NMR(溶媒:CDCl3、内部標準物質:TMS)δ:2.27(2H)、3.44(4H).
IR(ユニバーサルATR法)3289、1407、1232、630cm-1.
EI-MS 実測値[M-H]+:109、理論値[M]+:110
ビスプロパルギルカーボネート(下記式(1d)で表される化合物)の合成
攪拌装置付きの反応器にトリホスゲン51.8g(0.17モル:市販品(東京化成工業社製))を装入し、塩化メチレン210mlを加えて撹拌溶解した。続けて氷水浴を用いて10℃まで冷却した後にプロパルギルアルコール60.0g(1.07モル:市販品(東京化成工業社製))、ピリジン84.5g(1.07モル:市販品(和光純薬社製))を塩化メチレン210mlに溶解した溶液を1.5時間かけて滴下挿入し、さらに3時間撹拌した。続けて、トリホスゲン10.4g(0.035モル)、ピリジン16.9g(0.21モル)を塩化メチレン210mlに溶解した溶液を装入し、さらに2時間撹拌した。水、5%HCl水溶液、水、5%NaHCO3水溶液、水で分液洗浄を行い、有機層は硫酸マグネシウムで脱水した。ろ過して塩を除去した後にロータリーエバポレーターで溶媒を留去した後に真空ポンプで減圧乾燥して下記に示される化合物59.2g(収率80.3%)を得た。
1H-NMR(溶媒:CDCl3、内部標準物質:TMS)δ:2.55(2H)、4.76(4H).
IR(ユニバーサルATR法)3293、2131、1749、1439、1232、979、916、785、638、524cm-1.
ビスプロパルギルチオメチレン(下記式(1e)で表される化合物)の合成
攪拌装置付きの反応器に臭化プロパルギル37.8g(0.25モル:市販品(東京化成工業社製))を装入し、トルエン115mlを加えて撹拌溶解した。続けて氷水浴を用いて10℃まで冷却した後にメタンジチオール10.0g(0.125モル)、トリエチルアミン25.3g(0.25モル:市販品(和光純薬社製))を装入し、室温で攪拌した。水を装入し、分液洗浄を行い、有機層は硫酸マグネシウムで脱水し、ろ過して塩を除去した後にロータリーエバポレーターで溶媒を留去した。残った液体をカラムクロマトグラフィーで精製を行い、下記に示される化合物13.56g(収率69.5%)を得た。
1H-NMR(溶媒:CDCl3、内部標準物質:TMS)δ:2.26(2H)、3.38(4H)、4.02(2H).
ビスプロパルギルチオカーボネート(下記式(1f)で表される化合物)の合成
攪拌装置付きの反応器にトリホスゲン9.9g(0.033モル:市販品(東京化成工業社製))を装入し、塩化メチレン70mlを加えて撹拌溶解した。続けて氷水浴を用いて10℃まで冷却した後にプロパルギルチオール(参考製造例2の方法で製造)11.0g(0.017モル)、ピリジン13.2g(0.017モル)を塩化メチレン70mlに溶解した溶液を1時間かけて滴下挿入し、さらに1.5時間撹拌し、その後室温で1.5時間撹拌した。飽和NaHCO3水溶液で反応を停止し、水、5%HCl水溶液、水、5%NaHCO3水溶液、水で分液洗浄を行い、有機層は硫酸マグネシウムで脱水した。ろ過して塩を除去した後にロータリーエバポレーターで溶媒を留去した後に真空ポンプで減圧乾燥して下記に示される化合物3.8g(収率53.4%)を得た。
1H-NMR(溶媒:CDCl3、内部標準物質:TMS)δ:2.35(2H)、3.79(4H).
ビスプロパルギルチオカーバメート(下記式(1g)で表される化合物)の合成
スクリュー管に2.06ミリモル/gのプロパルギルチオールのトルエン溶液(参考製造例2の方法で製造)24.3g(0.05モル)を装入し、トルエン10mlを加えて撹拌した。続けてプロパルギルイソシアネート4.1g(0.05モル)を挿入し、室温で2日間撹拌した。シリカゲルを装入し、撹拌した後、シリカゲルをろ過して取り除き、ロータリーエバポレーターで溶媒を留去した後に真空ポンプで減圧乾燥して下記に示される化合物5.72g(収率74.7%)を得た。
1H-NMR(溶媒:CDCl3、内部標準物質:TMS)δ:2.23(1H)、2.28(1H)、3.71(2H)、4.12(2H)、5.54(1H).
2,4-ビス(プロパルギルチオ)-2,5-ジヒドロ-1,2-チアスチボール(下記式(1h)で表される化合物)の合成
攪拌装置付きの反応器に参考製造例1で合成したチオ酢酸プロパルギル14.8g(0.10モル)を装入し、メタノール100gに加えて撹拌溶解した。続けて氷水浴を用いて10℃まで冷却した後に28%ナトリウムメトキシドメタノール溶液12.9g(0.067モル)を1時間かけて滴下装入した。次に塩化アンチモン5.0g(0.022モル:市販品(和光純薬社製))をエタノール20gに溶解した溶液を20分かけて滴下装入した。装入後、15時間攪拌し、析出した固体をろ取した。析出物を50gのジクロロメタンに溶解し、50gの水で洗浄して塩を除去した後に分液した。有機層は硫酸マグネシウムで脱水し、ろ過して塩を除去した後にロータリーエバポレーターで溶媒を留去した。残った黄色固体を乾燥して下記に示される化合物4.60g(収率62.4%)を得た。
1H-NMR(溶媒:DMSO-d6、内部標準物質:TMS)δ:3.18(2H)、3.43(2H)、3.78(2H)、4.09(1H)、4.45(1H)、6.74(1H).
13C-NMR(溶媒:DMSO-d6)δ:16.0、20.7、43.9、73.5、73.9、79.6、83.6、126.9、156.1
IR(ユニバーサルATR法):3281、1553、1407、1238、1183、9652、629cm-1.
FAB-MS 実測値[M+H]+:335、理論値[M]+:334
室温(25℃)下、ガラスビーカーに参考製造例2で製造した化合物0.43gを秤取し、続けて1,1,3,3-テトラキス(メルカプトメチルチオ)プロパンを主成分とする混合物0.57gを秤取した。10℃で冷却しながら攪拌混合し、減圧脱気をおこなった。ガラスビーカーを反応器に入れて10℃で冷却しながら7日間静置後、オイルバスを用いて1時間かけて80℃まで加熱した。さらに重合オーブンに移して110℃で3時間加熱重合をおこなった。
得られた樹脂成形体の外観は透明であり、屈折率ne=1.745であった。
室温(25℃)下、ガラスビーカーに参考製造例2で製造した化合物0.27gを秤取し、続けて1,1,3,3-テトラキス(メルカプトメチルチオ)プロパン0.73gを主成分とする混合物を秤取した。10℃で冷却しながら攪拌混合し、減圧脱気をおこなった。ガラスビーカーを反応器に入れて10℃で冷却しながら7日間静置後、オイルバスを用いて1時間かけて80℃まで加熱した。さらに重合オーブンに移して100℃で2時間加熱重合をおこなった。
得られた樹脂成形体の外観は透明であり、屈折率ne=1.732であった。
室温(25℃)下、ガラスビーカーに参考製造例2で製造した化合物0.50gを秤取し、続けて1,1,3,3-テトラキス(メルカプトメチルチオ)プロパンを主成分とする混合物0.50gを秤取した。10℃で冷却しながら攪拌混合し、減圧脱気をおこなった。ガラスビーカーを反応器に入れて10℃で冷却しながら3時間静置後、室温(25℃)で2日間静置した。8時間かけて60℃まで昇温後、重合オーブンに移して9時間かけて60℃から100℃まで昇温した後に100℃で3時間加熱重合をおこなった。
得られた樹脂成形体の外観は透明であり、屈折率ne=1.732であった。
室温(25℃)下、ガラスビーカーに参考製造例2で製造した化合物0.47gを秤取し、続けて4-メルカプトメチル-1,8-ジメルカプト-3,6-ジチアオクタン0.53gを秤取した。10℃で冷却しながら攪拌混合し、減圧脱気をおこなった。ガラスビーカーを反応器に入れて10℃で冷却しながら3時間静置後、室温(25℃)で2日間静置した。8時間かけて60℃まで昇温後、重合オーブンに移して9時間かけて60℃から100℃まで昇温した後に100℃で3時間加熱重合をおこなった。
得られた樹脂成形体の外観は透明であり、屈折率ne=1.692であった。
室温(25℃)下、ガラスビーカーに参考製造例2で製造した化合物0.25gを秤取し、続けて4-メルカプトメチル-1,8-ジメルカプト-3,6-ジチアオクタンを主成分とする混合物0.75gを秤取した。攪拌混合し、減圧脱気をおこなった。重合オーブンに移して22時間かけて25℃から120℃まで昇温し加熱重合をおこなった。
得られた樹脂成形体の外観は透明であり、屈折率ne=1.730であった。
室温(25℃)下、ガラスビーカーに参考製造例5で製造した化合物0.25gを秤取し、続けて1,1,3,3-テトラキス(メルカプトメチルチオ)プロパンを主成分とする混合物0.75gを秤取した。10℃で冷却しながら攪拌混合し、減圧脱気をおこなった。重合オーブンに移して22時間かけて25℃から100℃まで昇温し加熱重合をおこなった。得られた樹脂成形体の外観は透明であり、屈折率ne=1.697であった。
室温(25℃)下、ガラスビーカーに参考製造例5で製造した化合物0.27gを秤取し、続けて4,8または4,7または5,7-ジメルカプトメチル-1,11-ジメルカプト-3,6,9-トリチアウンデカンを主成分とする混合物0.73gを秤取した。10℃で冷却しながら攪拌混合し、減圧脱気をおこなった。重合オーブンに移して22時間かけて25℃から100℃まで昇温し加熱重合をおこなった。得られた樹脂成形体の外観は透明であり、屈折率ne=1.668であった。
室温(25℃)下、ガラスビーカーに実施例1で製造した化合物0.27gを秤取し、続けて1,1,3,3-テトラキス(メルカプトメチルチオ)プロパンを主成分とする混合物0.73gを秤取した。10℃で冷却しながら攪拌混合し、減圧脱気をおこなった。重合オーブンに移して22時間かけて25℃から100℃まで昇温し加熱重合をおこなった。得られた樹脂成形体は屈折率ne=1.743であった。
室温(25℃)下、ガラスビーカーに実施例1で製造した化合物0.30gを秤取し、続けて4,8または4,7または5,7-ジメルカプトメチル-1,11-ジメルカプト-3,6,9-トリチアウンデカンを主成分とする混合物0.70gを秤取した。10℃で冷却しながら攪拌混合し、減圧脱気をおこなった。重合オーブンに移して22時間かけて25℃から100℃まで昇温し加熱重合をおこなった。得られた樹脂成形体は屈折率ne=1.696であった。
室温(25℃)下、ガラスビーカーに実施例2で製造した化合物0.29gを秤取し、続けて1,1,3,3-テトラキス(メルカプトメチルチオ)プロパンを主成分とする混合物0.71gを秤取した。10℃で冷却しながら攪拌混合し、減圧脱気をおこなった。重合オーブンに移して22時間かけて25℃から100℃まで昇温し加熱重合をおこなった。得られた樹脂成形体の外観は透明であり、屈折率ne=1.741であった。
室温(25℃)下、ガラスビーカーに実施例2で製造した化合物0.32gを秤取し、続けて4,8または4,7または5,7-ジメルカプトメチル-1,11-ジメルカプト-3,6,9-トリチアウンデカンを主成分とする混合物0.68gを秤取した。10℃で冷却しながら攪拌混合し、減圧脱気をおこなった。重合オーブンに移して22時間かけて25℃から100℃まで昇温し加熱重合をおこなった。得られた樹脂成形体の外観は透明であり、屈折率ne=1.709であった。
室温(25℃)下、ガラスビーカーに実施例3で製造した化合物0.27gを秤取し、続けて1,1,3,3-テトラキス(メルカプトメチルチオ)プロパンを主成分とする混合物0.73gを秤取した。10℃で冷却しながら攪拌混合し、減圧脱気をおこなった。重合オーブンに移して22時間かけて25℃から100℃まで昇温し加熱重合をおこなった。得られた樹脂成形体の外観は透明であり、屈折率ne=1.730であった。
室温(25℃)下、ガラスビーカーに実施例3で製造した化合物0.30gを秤取し、続けて4,8または4,7または5,7-ジメルカプトメチル-1,11-ジメルカプト-3,6,9-トリチアウンデカンを主成分とする混合物0.70gを秤取した。10℃で冷却しながら攪拌混合し、減圧脱気をおこなった。重合オーブンに移して22時間かけて25℃から120℃まで昇温し加熱重合をおこなった。得られた樹脂成形体の外観は透明であり、屈折率ne=1.698であった。
室温(25℃)下、ガラスビーカーに実施例4で製造した式(1h)の化合物0.67gを秤取し、続けて4-メルカプトメチル-1,8-ジメルカプト-3,6-ジチアオクタン0.52gを秤取した。80℃に加熱して溶解させた。70℃まで一旦冷却した後に重合触媒として過2-エチルヘキサン酸t-ブチルを1mg(0.1重量部:市販品(日本油脂社製))加えて減圧脱気し、ガラスモールドとテープよりなる注型モールド中へ該重合性化合物を注入した。加熱オーブン中へ入れ90℃で16時間、100℃で3時間重合を行った。
得られた樹脂成形体の外観は透明であり、屈折率neは1.795であった。
[a1]下記一般式(1-6)で表される新規な含硫黄アルキン化合物。
[a2] [a1]に記載の含硫黄アルキン化合物を含む重合性組成物。
[a3] さらに、チオール化合物を含む[a2]に記載の重合性組成物。
[a4] 前記チオール化合物は、4-メルカプトメチル-1,8-ジメルカプト-3,6-ジチアオクタン、4,8または4,7または5,7-ジメルカプトメチル-1,11-ジメルカプト-3,6,9-トリチアウンデカン、ペンタエリスリトールテトラキス(2-メルカプトアセテート)、ペンタエリスリトールテトラキス(3-メルカプトプロピオネート)、2,5-ビス(メルカプトメチル)-1,4-ジチアン、ビス(メルカプトエチル)スルフィド、1,1,3,3-テトラキス(メルカプトメチルチオ)プロパン、4,6-ビス(メルカプトメチルチオ)-1,3-ジチアン、2-(2,2-ビス(メルカプトメチルチオ)エチル)-1,3-ジチエタンから選ばれる1種以上のポリチオール化合物を含む、[a3]に記載の重合性組成物。
[a5] [a2]~[a4]のいずれかに記載の重合性組成物を硬化させて得られる成形体。
[a6] [a5]に記載の成形体からなる光学材料。
[a7] [a5]に記載の成形体からなるプラスチックレンズ。
[b1] 下記式(1h)で表される新規なアンチモン含有化合物。
[b3] さらに、チオール化合物を含む[b2]に記載の重合性組成物。
[b4] 前記チオール化合物は、4-メルカプトメチル-1,8-ジメルカプト-3,6-ジチアオクタン、4,8または4,7または5,7-ジメルカプトメチル-1,11-ジメルカプト-3,6,9-トリチアウンデカン、ペンタエリスリトールテトラキスメルカプトアセテート、ペンタエリスリトールテトラキスメルカプトプロピオネート、2,5-ビス(メルカプトメチル)-1,4-ジチアン、ビス(メルカプトエチル)スルフィド、1,1,3,3-テトラキス(メルカプトメチルチオ)プロパン、4,6-ビス(メルカプトメチルチオ)-1,3-ジチアン、2-(2,2-ビス(メルカプトメチルチオ)エチル)-1,3-ジチエタンから選ばれる1種以上のポリチオール化合物を含む、[b3]に記載の重合性組成物。
[b5] [b2]~[b4]のいずれかに記載の重合性組成物を硬化させて得られる成形体。
[b6] [b5]に記載の成形体からなる光学材料。
[b7] [b5]に記載の成形体からなるプラスチックレンズ。
[b8] プロパギルのチオアセチル化物もしくはプロパルギルチオールに、反応に不活性な溶媒および塩基の存在下で、アンチモンハライドを作用させる、下記式(1h)で表されるアンチモン含有化合物の製造方法。
Claims (10)
- さらに、チオール化合物を含む請求項1~3のいずれかに記載の重合性組成物。
- 前記チオール化合物は、4-メルカプトメチル-1,8-ジメルカプト-3,6-ジチアオクタン、4,8または4,7または5,7-ジメルカプトメチル-1,11-ジメルカプト-3,6,9-トリチアウンデカン、ペンタエリスリトールテトラキス(2-メルカプトアセテート)、ペンタエリスリトールテトラキス(3-メルカプトプロピオネート)、2,5-ビス(メルカプトメチル)-1,4-ジチアン、ビス(メルカプトエチル)スルフィド、1,1,3,3-テトラキス(メルカプトメチルチオ)プロパン、4,6-ビス(メルカプトメチルチオ)-1,3-ジチアン、2-(2,2-ビス(メルカプトメチルチオ)エチル)-1,3-ジチエタンから選ばれる1種以上のポリチオール化合物を含む、請求項4に記載の重合性組成物。
- 請求項1~5のいずれかに記載の重合性組成物を硬化させた成形体。
- 請求項6に記載の成形体からなる光学材料。
- 請求項6に記載の成形体からなるプラスチックレンズ。
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