JP4809020B2 - ラジカル重合性含硫黄化合物およびラジカル重合性含硫黄ポリマー - Google Patents
ラジカル重合性含硫黄化合物およびラジカル重合性含硫黄ポリマー Download PDFInfo
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- JP4809020B2 JP4809020B2 JP2005255338A JP2005255338A JP4809020B2 JP 4809020 B2 JP4809020 B2 JP 4809020B2 JP 2005255338 A JP2005255338 A JP 2005255338A JP 2005255338 A JP2005255338 A JP 2005255338A JP 4809020 B2 JP4809020 B2 JP 4809020B2
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- Prior art keywords
- allyl
- meth
- radically polymerizable
- acid
- sulfur
- Prior art date
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- 229920000642 polymer Polymers 0.000 title claims abstract description 103
- 150000001875 compounds Chemical class 0.000 title claims abstract description 98
- 229910052717 sulfur Inorganic materials 0.000 title claims abstract description 98
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 title claims abstract description 97
- 239000011593 sulfur Substances 0.000 title claims abstract description 97
- 239000000203 mixture Substances 0.000 claims abstract description 75
- 239000000463 material Substances 0.000 claims abstract description 20
- 230000003287 optical effect Effects 0.000 claims abstract description 16
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 52
- -1 allyl ester compound Chemical class 0.000 claims description 49
- 125000000217 alkyl group Chemical group 0.000 claims description 35
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 35
- 125000004432 carbon atom Chemical group C* 0.000 claims description 31
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 15
- 238000012656 cationic ring opening polymerization Methods 0.000 claims description 8
- RWMHFANJOASIHT-UHFFFAOYSA-N dibenzyl 2-hydroxybutanedioate Chemical compound C=1C=CC=CC=1COC(=O)C(O)CC(=O)OCC1=CC=CC=C1 RWMHFANJOASIHT-UHFFFAOYSA-N 0.000 claims description 7
- 238000007151 ring opening polymerisation reaction Methods 0.000 claims description 7
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 claims description 7
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 claims description 6
- ATCRIUVQKHMXSH-UHFFFAOYSA-N 2,4-dichlorobenzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1Cl ATCRIUVQKHMXSH-UHFFFAOYSA-N 0.000 claims description 6
- LULAYUGMBFYYEX-UHFFFAOYSA-N 3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 claims description 6
- WTIFDVLCDRBEJK-VAWYXSNFSA-N diphenyl (e)-but-2-enedioate Chemical compound C=1C=CC=CC=1OC(=O)/C=C/C(=O)OC1=CC=CC=C1 WTIFDVLCDRBEJK-VAWYXSNFSA-N 0.000 claims description 5
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- MRUDNSFOFOQZDA-UHFFFAOYSA-N 2,6-dichlorobenzoic acid Chemical compound OC(=O)C1=C(Cl)C=CC=C1Cl MRUDNSFOFOQZDA-UHFFFAOYSA-N 0.000 claims description 3
- XRXMNWGCKISMOH-UHFFFAOYSA-N 2-bromobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Br XRXMNWGCKISMOH-UHFFFAOYSA-N 0.000 claims description 3
- IKCLCGXPQILATA-UHFFFAOYSA-N 2-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-UHFFFAOYSA-N 0.000 claims description 3
- UOBYKYZJUGYBDK-UHFFFAOYSA-N 2-naphthoic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CC=C21 UOBYKYZJUGYBDK-UHFFFAOYSA-N 0.000 claims description 3
- ILYSAKHOYBPSPC-UHFFFAOYSA-N 2-phenylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C1=CC=CC=C1 ILYSAKHOYBPSPC-UHFFFAOYSA-N 0.000 claims description 3
- VOIZNVUXCQLQHS-UHFFFAOYSA-N 3-bromobenzoic acid Chemical compound OC(=O)C1=CC=CC(Br)=C1 VOIZNVUXCQLQHS-UHFFFAOYSA-N 0.000 claims description 3
- XNLWJFYYOIRPIO-UHFFFAOYSA-N 3-phenylbenzoic acid Chemical compound OC(=O)C1=CC=CC(C=2C=CC=CC=2)=C1 XNLWJFYYOIRPIO-UHFFFAOYSA-N 0.000 claims description 3
- TUXYZHVUPGXXQG-UHFFFAOYSA-N 4-bromobenzoic acid Chemical compound OC(=O)C1=CC=C(Br)C=C1 TUXYZHVUPGXXQG-UHFFFAOYSA-N 0.000 claims description 3
- XRHGYUZYPHTUJZ-UHFFFAOYSA-N 4-chlorobenzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1 XRHGYUZYPHTUJZ-UHFFFAOYSA-N 0.000 claims description 3
- NNJMFJSKMRYHSR-UHFFFAOYSA-N 4-phenylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=CC=C1 NNJMFJSKMRYHSR-UHFFFAOYSA-N 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 claims description 3
- GWZCCUDJHOGOSO-UHFFFAOYSA-N diphenic acid Chemical compound OC(=O)C1=CC=CC=C1C1=CC=CC=C1C(O)=O GWZCCUDJHOGOSO-UHFFFAOYSA-N 0.000 claims description 3
- 239000005711 Benzoic acid Substances 0.000 claims description 2
- 235000010233 benzoic acid Nutrition 0.000 claims description 2
- CPZVJYPXOWWFSW-VAWYXSNFSA-N dibenzyl (e)-but-2-enedioate Chemical compound C=1C=CC=CC=1COC(=O)/C=C/C(=O)OCC1=CC=CC=C1 CPZVJYPXOWWFSW-VAWYXSNFSA-N 0.000 claims description 2
- 241000238366 Cephalopoda Species 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 23
- 238000006116 polymerization reaction Methods 0.000 abstract description 5
- 238000007142 ring opening reaction Methods 0.000 abstract description 3
- 150000001768 cations Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 31
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
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- 238000001723 curing Methods 0.000 description 26
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 238000000034 method Methods 0.000 description 23
- 239000000047 product Substances 0.000 description 22
- 239000000243 solution Substances 0.000 description 22
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000002904 solvent Substances 0.000 description 18
- 238000005259 measurement Methods 0.000 description 17
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
- 239000000741 silica gel Substances 0.000 description 16
- 229910002027 silica gel Inorganic materials 0.000 description 16
- 238000005160 1H NMR spectroscopy Methods 0.000 description 15
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 14
- 150000002500 ions Chemical class 0.000 description 13
- 238000010526 radical polymerization reaction Methods 0.000 description 13
- 239000003054 catalyst Substances 0.000 description 12
- 239000002002 slurry Substances 0.000 description 12
- ROLAGNYPWIVYTG-UHFFFAOYSA-N 1,2-bis(4-methoxyphenyl)ethanamine;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1CC(N)C1=CC=C(OC)C=C1 ROLAGNYPWIVYTG-UHFFFAOYSA-N 0.000 description 11
- 125000000524 functional group Chemical group 0.000 description 11
- 229910018286 SbF 6 Inorganic materials 0.000 description 10
- 239000000178 monomer Substances 0.000 description 10
- 238000000746 purification Methods 0.000 description 10
- 238000005227 gel permeation chromatography Methods 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 229920005989 resin Polymers 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- JHQVCQDWGSXTFE-UHFFFAOYSA-N 2-(2-prop-2-enoxycarbonyloxyethoxy)ethyl prop-2-enyl carbonate Chemical compound C=CCOC(=O)OCCOCCOC(=O)OCC=C JHQVCQDWGSXTFE-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 8
- 239000003963 antioxidant agent Substances 0.000 description 8
- 239000007795 chemical reaction product Substances 0.000 description 8
- 229920003023 plastic Polymers 0.000 description 8
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- 239000007870 radical polymerization initiator Substances 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- OIRDBPQYVWXNSJ-UHFFFAOYSA-N methyl trifluoromethansulfonate Chemical compound COS(=O)(=O)C(F)(F)F OIRDBPQYVWXNSJ-UHFFFAOYSA-N 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 230000002194 synthesizing effect Effects 0.000 description 6
- 238000001879 gelation Methods 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 5
- 230000003078 antioxidant effect Effects 0.000 description 4
- ZDNFTNPFYCKVTB-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,4-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=C(C(=O)OCC=C)C=C1 ZDNFTNPFYCKVTB-UHFFFAOYSA-N 0.000 description 4
- 125000002091 cationic group Chemical group 0.000 description 4
- 238000010538 cationic polymerization reaction Methods 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
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- 238000009835 boiling Methods 0.000 description 2
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- XPDWGBQVDMORPB-UHFFFAOYSA-N trifluoromethane acid Natural products FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 1
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- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
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Images
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- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
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| AU5066598A (en) * | 1996-12-04 | 1998-06-29 | Kyowa Hakko Kogyo Co. Ltd. | Dithiocarbonate composition |
| JPH11292969A (ja) * | 1998-04-06 | 1999-10-26 | Sanyo Chem Ind Ltd | チオカーボネート系重合体 |
| US6759484B1 (en) * | 1999-09-30 | 2004-07-06 | Kyowa Yuka Co., Ltd. | Method of diminishing odor emission |
| PL197400B1 (pl) * | 2002-04-29 | 2008-03-31 | Politechnika Krakowska | Sposób obniżania lepkości żywic epoksydowych |
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| TW200616993A (en) * | 2004-09-21 | 2006-06-01 | Showa Denko Kk | Radical polymerizable sulfur-containing compound and radical polymerizable sulfur-containing polymer |
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