JP2015518077A - エピスルフィド官能基を有するエチレン性不飽和モノマーを含有する重合可能な組成物および関連する方法 - Google Patents
エピスルフィド官能基を有するエチレン性不飽和モノマーを含有する重合可能な組成物および関連する方法 Download PDFInfo
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- JP2015518077A JP2015518077A JP2015509177A JP2015509177A JP2015518077A JP 2015518077 A JP2015518077 A JP 2015518077A JP 2015509177 A JP2015509177 A JP 2015509177A JP 2015509177 A JP2015509177 A JP 2015509177A JP 2015518077 A JP2015518077 A JP 2015518077A
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- Prior art keywords
- composition
- polymerizable composition
- ethylenically unsaturated
- polymerizable
- isourea
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 109
- 239000000178 monomer Substances 0.000 title claims abstract description 58
- 238000000034 method Methods 0.000 title claims abstract description 45
- 150000003553 thiiranes Chemical group 0.000 title description 2
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 47
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 28
- 238000006243 chemical reaction Methods 0.000 claims abstract description 25
- 239000003505 polymerization initiator Substances 0.000 claims abstract description 21
- 239000003054 catalyst Substances 0.000 claims abstract description 20
- 150000001875 compounds Chemical class 0.000 claims abstract description 19
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000011593 sulfur Substances 0.000 claims abstract description 8
- 238000012644 addition polymerization Methods 0.000 claims abstract description 5
- -1 β-epithiopropyl functional group Chemical group 0.000 claims description 45
- 239000000047 product Substances 0.000 claims description 36
- 230000003287 optical effect Effects 0.000 claims description 12
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 12
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 11
- 239000007795 chemical reaction product Substances 0.000 claims description 9
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- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 229910052796 boron Inorganic materials 0.000 claims description 5
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims description 5
- 229940117900 2,2-bis(4-glycidyloxyphenyl)propane Drugs 0.000 claims description 4
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 claims description 4
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 4
- 229910001507 metal halide Inorganic materials 0.000 claims description 4
- 150000005309 metal halides Chemical class 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- 235000005985 organic acids Nutrition 0.000 claims description 4
- 150000004714 phosphonium salts Chemical group 0.000 claims description 4
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 4
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium group Chemical group [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 claims description 4
- 238000004383 yellowing Methods 0.000 claims description 4
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 claims description 3
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims 4
- SSOVVTOURMQUSM-UHFFFAOYSA-N 2-[(4-propylphenoxy)methyl]oxirane Chemical compound C1=CC(CCC)=CC=C1OCC1OC1 SSOVVTOURMQUSM-UHFFFAOYSA-N 0.000 claims 2
- 125000005250 alkyl acrylate group Chemical group 0.000 claims 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 1
- 125000000524 functional group Chemical group 0.000 abstract 6
- 125000000217 alkyl group Chemical group 0.000 description 29
- 230000000052 comparative effect Effects 0.000 description 18
- 125000003118 aryl group Chemical group 0.000 description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- CJJFVKUSLZKLOC-UHFFFAOYSA-N 1-(cyclohexylideneamino)-1,3-di(propan-2-yloxy)urea Chemical compound C(C)(C)ON(C(O)=NOC(C)C)N=C1CCCCC1 CJJFVKUSLZKLOC-UHFFFAOYSA-N 0.000 description 13
- 239000007787 solid Substances 0.000 description 12
- 239000003999 initiator Substances 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- 125000000753 cycloalkyl group Chemical group 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical class C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 6
- 125000003710 aryl alkyl group Chemical group 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 150000002978 peroxides Chemical class 0.000 description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 4
- 125000002252 acyl group Chemical group 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 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 4
- 125000003367 polycyclic group Chemical group 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 239000000539 dimer Substances 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 3
- 239000013638 trimer Substances 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- 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 2
- RSLIVJSXOOOGSR-UHFFFAOYSA-N 2-(thiiran-2-ylmethoxymethyl)thiirane Chemical compound C1SC1COCC1CS1 RSLIVJSXOOOGSR-UHFFFAOYSA-N 0.000 description 2
- MLGITEWCALEOOJ-UHFFFAOYSA-N 2-(thiiran-2-ylmethylsulfanylmethyl)thiirane Chemical compound C1SC1CSCC1CS1 MLGITEWCALEOOJ-UHFFFAOYSA-N 0.000 description 2
- CEXQWAAGPPNOQF-UHFFFAOYSA-N 2-phenoxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOC1=CC=CC=C1 CEXQWAAGPPNOQF-UHFFFAOYSA-N 0.000 description 2
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N 4-methylimidazole Chemical compound CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- IAXXETNIOYFMLW-COPLHBTASA-N [(1s,3s,4s)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] 2-methylprop-2-enoate Chemical compound C1C[C@]2(C)[C@@H](OC(=O)C(=C)C)C[C@H]1C2(C)C IAXXETNIOYFMLW-COPLHBTASA-N 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 description 2
- VPLLTGLLUHLIHA-UHFFFAOYSA-N dicyclohexyl(phenyl)phosphane Chemical compound C1CCCCC1P(C=1C=CC=CC=1)C1CCCCC1 VPLLTGLLUHLIHA-UHFFFAOYSA-N 0.000 description 2
- LVTCZSBUROAWTE-UHFFFAOYSA-N diethyl(phenyl)phosphane Chemical compound CCP(CC)C1=CC=CC=C1 LVTCZSBUROAWTE-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 229940119545 isobornyl methacrylate Drugs 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 150000003003 phosphines Chemical class 0.000 description 2
- 239000002685 polymerization catalyst Substances 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- CHYBTAZWINMGHA-UHFFFAOYSA-N tetraoctylazanium Chemical compound CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)CCCCCCCC CHYBTAZWINMGHA-UHFFFAOYSA-N 0.000 description 2
- VOVUARRWDCVURC-UHFFFAOYSA-N thiirane Chemical compound C1CS1 VOVUARRWDCVURC-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- YWWDBCBWQNCYNR-UHFFFAOYSA-N trimethylphosphine Chemical compound CP(C)C YWWDBCBWQNCYNR-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- NNJRPZZMNBNRFJ-UHFFFAOYSA-N (3-ethoxy-3-oxo-2-phenylpropyl)azanium;chloride Chemical compound Cl.CCOC(=O)C(CN)C1=CC=CC=C1 NNJRPZZMNBNRFJ-UHFFFAOYSA-N 0.000 description 1
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- VSMRPKQQWDXXQA-UHFFFAOYSA-N (cyclohexylideneamino) n,n'-dicyclohexylcarbamimidate Chemical compound C1CCCCC1NC(ON=C1CCCCC1)=NC1CCCCC1 VSMRPKQQWDXXQA-UHFFFAOYSA-N 0.000 description 1
- FTTATHOUSOIFOQ-UHFFFAOYSA-N 1,2,3,4,6,7,8,8a-octahydropyrrolo[1,2-a]pyrazine Chemical compound C1NCCN2CCCC21 FTTATHOUSOIFOQ-UHFFFAOYSA-N 0.000 description 1
- SSUJUUNLZQVZMO-UHFFFAOYSA-N 1,2,3,4,8,9,10,10a-octahydropyrimido[1,2-a]azepine Chemical compound C1CCC=CN2CCCNC21 SSUJUUNLZQVZMO-UHFFFAOYSA-N 0.000 description 1
- XGINAUQXFXVBND-UHFFFAOYSA-N 1,2,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrimidine Chemical compound N1CC=CN2CCCC21 XGINAUQXFXVBND-UHFFFAOYSA-N 0.000 description 1
- PWCSZEGUPHKLOL-UHFFFAOYSA-M 1,2-dimethylpyridin-1-ium;bromide Chemical compound [Br-].CC1=CC=CC=[N+]1C PWCSZEGUPHKLOL-UHFFFAOYSA-M 0.000 description 1
- BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- FBHPRUXJQNWTEW-UHFFFAOYSA-N 1-benzyl-2-methylimidazole Chemical compound CC1=NC=CN1CC1=CC=CC=C1 FBHPRUXJQNWTEW-UHFFFAOYSA-N 0.000 description 1
- KKKDZZRICRFGSD-UHFFFAOYSA-N 1-benzylimidazole Chemical compound C1=CN=CN1CC1=CC=CC=C1 KKKDZZRICRFGSD-UHFFFAOYSA-N 0.000 description 1
- VMKOFRJSULQZRM-UHFFFAOYSA-N 1-bromooctane Chemical compound CCCCCCCCBr VMKOFRJSULQZRM-UHFFFAOYSA-N 0.000 description 1
- QVHDOABFJHOTIT-UHFFFAOYSA-M 1-butyl-2-methylpyridin-1-ium;bromide Chemical compound [Br-].CCCC[N+]1=CC=CC=C1C QVHDOABFJHOTIT-UHFFFAOYSA-M 0.000 description 1
- MCMFEZDRQOJKMN-UHFFFAOYSA-N 1-butylimidazole Chemical compound CCCCN1C=CN=C1 MCMFEZDRQOJKMN-UHFFFAOYSA-N 0.000 description 1
- KVBQNFMTEUEOCD-UHFFFAOYSA-M 1-butylpyridin-1-ium;bromide Chemical compound [Br-].CCCC[N+]1=CC=CC=C1 KVBQNFMTEUEOCD-UHFFFAOYSA-M 0.000 description 1
- MYGCSEZBEJBLBL-UHFFFAOYSA-M 1-dodecyl-2-methylpyridin-1-ium;bromide Chemical compound [Br-].CCCCCCCCCCCC[N+]1=CC=CC=C1C MYGCSEZBEJBLBL-UHFFFAOYSA-M 0.000 description 1
- QTXZDFXPUPKBJC-UHFFFAOYSA-M 1-ethyl-2-methylpyridin-1-ium;bromide Chemical compound [Br-].CC[N+]1=CC=CC=C1C QTXZDFXPUPKBJC-UHFFFAOYSA-M 0.000 description 1
- IWDFHWZHHOSSGR-UHFFFAOYSA-N 1-ethylimidazole Chemical compound CCN1C=CN=C1 IWDFHWZHHOSSGR-UHFFFAOYSA-N 0.000 description 1
- ABFDKXBSQCTIKH-UHFFFAOYSA-M 1-ethylpyridin-1-ium;bromide Chemical compound [Br-].CC[N+]1=CC=CC=C1 ABFDKXBSQCTIKH-UHFFFAOYSA-M 0.000 description 1
- GQKLOZNOGXJOSN-UHFFFAOYSA-M 1-hexyl-2-methylpyridin-1-ium;bromide Chemical compound [Br-].CCCCCC[N+]1=CC=CC=C1C GQKLOZNOGXJOSN-UHFFFAOYSA-M 0.000 description 1
- SZRSEFNUSHACPD-UHFFFAOYSA-M 1-hexylpyridin-1-ium;bromide Chemical compound [Br-].CCCCCC[N+]1=CC=CC=C1 SZRSEFNUSHACPD-UHFFFAOYSA-M 0.000 description 1
- WTDKNKIQGBNMKG-UHFFFAOYSA-M 1-methylpyridin-1-ium;bromide Chemical compound [Br-].C[N+]1=CC=CC=C1 WTDKNKIQGBNMKG-UHFFFAOYSA-M 0.000 description 1
- LNKPCMOUFKLBCM-UHFFFAOYSA-M 1-octylpyridin-1-ium;bromide Chemical compound [Br-].CCCCCCCC[N+]1=CC=CC=C1 LNKPCMOUFKLBCM-UHFFFAOYSA-M 0.000 description 1
- SEULWJSKCVACTH-UHFFFAOYSA-N 1-phenylimidazole Chemical compound C1=NC=CN1C1=CC=CC=C1 SEULWJSKCVACTH-UHFFFAOYSA-N 0.000 description 1
- PKCPMTJMGADWTA-UHFFFAOYSA-N 1-undecylimidazole Chemical compound CCCCCCCCCCCN1C=CN=C1 PKCPMTJMGADWTA-UHFFFAOYSA-N 0.000 description 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003748 selenium group Chemical group *[Se]* 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000001542 size-exclusion chromatography Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 1
- MCZDHTKJGDCTAE-UHFFFAOYSA-M tetrabutylazanium;acetate Chemical compound CC([O-])=O.CCCC[N+](CCCC)(CCCC)CCCC MCZDHTKJGDCTAE-UHFFFAOYSA-M 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- BJQWBACJIAKDTJ-UHFFFAOYSA-N tetrabutylphosphanium Chemical compound CCCC[P+](CCCC)(CCCC)CCCC BJQWBACJIAKDTJ-UHFFFAOYSA-N 0.000 description 1
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 1
- IBWGNZVCJVLSHB-UHFFFAOYSA-M tetrabutylphosphanium;chloride Chemical compound [Cl-].CCCC[P+](CCCC)(CCCC)CCCC IBWGNZVCJVLSHB-UHFFFAOYSA-M 0.000 description 1
- CCIYPTIBRAUPLQ-UHFFFAOYSA-M tetrabutylphosphanium;iodide Chemical compound [I-].CCCC[P+](CCCC)(CCCC)CCCC CCIYPTIBRAUPLQ-UHFFFAOYSA-M 0.000 description 1
- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 1
- YMBCJWGVCUEGHA-UHFFFAOYSA-M tetraethylammonium chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC YMBCJWGVCUEGHA-UHFFFAOYSA-M 0.000 description 1
- GTCDARUMAMVCRO-UHFFFAOYSA-M tetraethylazanium;acetate Chemical compound CC([O-])=O.CC[N+](CC)(CC)CC GTCDARUMAMVCRO-UHFFFAOYSA-M 0.000 description 1
- LIXPXSXEKKHIRR-UHFFFAOYSA-M tetraethylphosphanium;bromide Chemical compound [Br-].CC[P+](CC)(CC)CC LIXPXSXEKKHIRR-UHFFFAOYSA-M 0.000 description 1
- FBOJNMRAZJRCNS-UHFFFAOYSA-M tetraethylphosphanium;chloride Chemical compound [Cl-].CC[P+](CC)(CC)CC FBOJNMRAZJRCNS-UHFFFAOYSA-M 0.000 description 1
- SYZCZDCAEVUSPM-UHFFFAOYSA-M tetrahexylazanium;bromide Chemical compound [Br-].CCCCCC[N+](CCCCCC)(CCCCCC)CCCCCC SYZCZDCAEVUSPM-UHFFFAOYSA-M 0.000 description 1
- ODTSDWCGLRVBHJ-UHFFFAOYSA-M tetrahexylazanium;chloride Chemical compound [Cl-].CCCCCC[N+](CCCCCC)(CCCCCC)CCCCCC ODTSDWCGLRVBHJ-UHFFFAOYSA-M 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- DDFYFBUWEBINLX-UHFFFAOYSA-M tetramethylammonium bromide Chemical compound [Br-].C[N+](C)(C)C DDFYFBUWEBINLX-UHFFFAOYSA-M 0.000 description 1
- MRYQZMHVZZSQRT-UHFFFAOYSA-M tetramethylazanium;acetate Chemical compound CC([O-])=O.C[N+](C)(C)C MRYQZMHVZZSQRT-UHFFFAOYSA-M 0.000 description 1
- ZTXFOCMYRCGSMU-UHFFFAOYSA-M tetramethylphosphanium;bromide Chemical compound [Br-].C[P+](C)(C)C ZTXFOCMYRCGSMU-UHFFFAOYSA-M 0.000 description 1
- NJFUXFRJVIXVSG-UHFFFAOYSA-M tetramethylphosphanium;chloride Chemical compound [Cl-].C[P+](C)(C)C NJFUXFRJVIXVSG-UHFFFAOYSA-M 0.000 description 1
- QBVXKDJEZKEASM-UHFFFAOYSA-M tetraoctylammonium bromide Chemical compound [Br-].CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)CCCCCCCC QBVXKDJEZKEASM-UHFFFAOYSA-M 0.000 description 1
- BRKFQVAOMSWFDU-UHFFFAOYSA-M tetraphenylphosphanium;bromide Chemical compound [Br-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BRKFQVAOMSWFDU-UHFFFAOYSA-M 0.000 description 1
- 238000007725 thermal activation Methods 0.000 description 1
- OXUABORVCCLQJI-UHFFFAOYSA-N thiiran-2-ylmethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1CS1 OXUABORVCCLQJI-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- IFXORIIYQORRMJ-UHFFFAOYSA-N tribenzylphosphane Chemical compound C=1C=CC=CC=1CP(CC=1C=CC=CC=1)CC1=CC=CC=C1 IFXORIIYQORRMJ-UHFFFAOYSA-N 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- LWBLDXRXGCRDDS-UHFFFAOYSA-M tributylsulfanium;bromide Chemical compound [Br-].CCCC[S+](CCCC)CCCC LWBLDXRXGCRDDS-UHFFFAOYSA-M 0.000 description 1
- FZVBSYTWAMIINE-UHFFFAOYSA-M tributylsulfanium;chloride Chemical compound [Cl-].CCCC[S+](CCCC)CCCC FZVBSYTWAMIINE-UHFFFAOYSA-M 0.000 description 1
- HUCQSHDLMUWBPS-UHFFFAOYSA-M tributylsulfanium;iodide Chemical compound [I-].CCCC[S+](CCCC)CCCC HUCQSHDLMUWBPS-UHFFFAOYSA-M 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- DMIDQAQLESZBGF-UHFFFAOYSA-M triethyl(octyl)azanium;chloride Chemical compound [Cl-].CCCCCCCC[N+](CC)(CC)CC DMIDQAQLESZBGF-UHFFFAOYSA-M 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- ANUSMYJRISPAKG-UHFFFAOYSA-M triethylsulfanium;bromide Chemical compound [Br-].CC[S+](CC)CC ANUSMYJRISPAKG-UHFFFAOYSA-M 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- HMSUGYLLDNYYOZ-UHFFFAOYSA-M trihexylsulfanium;bromide Chemical compound [Br-].CCCCCC[S+](CCCCCC)CCCCCC HMSUGYLLDNYYOZ-UHFFFAOYSA-M 0.000 description 1
- IGNTWNVBGLNYDV-UHFFFAOYSA-N triisopropylphosphine Chemical compound CC(C)P(C(C)C)C(C)C IGNTWNVBGLNYDV-UHFFFAOYSA-N 0.000 description 1
- AQZSPJRLCJSOED-UHFFFAOYSA-M trimethyl(octyl)azanium;chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(C)C AQZSPJRLCJSOED-UHFFFAOYSA-M 0.000 description 1
- GOTIICCWNAPLMN-UHFFFAOYSA-M trimethylsulfanium;bromide Chemical compound [Br-].C[S+](C)C GOTIICCWNAPLMN-UHFFFAOYSA-M 0.000 description 1
- RMZAYIKUYWXQPB-UHFFFAOYSA-N trioctylphosphane Chemical compound CCCCCCCCP(CCCCCCCC)CCCCCCCC RMZAYIKUYWXQPB-UHFFFAOYSA-N 0.000 description 1
- MNEDTFPROHJBIP-UHFFFAOYSA-M trioctylsulfanium;bromide Chemical compound [Br-].CCCCCCCC[S+](CCCCCCCC)CCCCCCCC MNEDTFPROHJBIP-UHFFFAOYSA-M 0.000 description 1
- VMJFYMAHEGJHFH-UHFFFAOYSA-M triphenylsulfanium;bromide Chemical compound [Br-].C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 VMJFYMAHEGJHFH-UHFFFAOYSA-M 0.000 description 1
- ZFEAYIKULRXTAR-UHFFFAOYSA-M triphenylsulfanium;chloride Chemical compound [Cl-].C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 ZFEAYIKULRXTAR-UHFFFAOYSA-M 0.000 description 1
- CVJLQNNJZBCTLI-UHFFFAOYSA-M triphenylsulfanium;iodide Chemical compound [I-].C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 CVJLQNNJZBCTLI-UHFFFAOYSA-M 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- LFNXCUNDYSYVJY-UHFFFAOYSA-N tris(3-methylphenyl)phosphane Chemical compound CC1=CC=CC(P(C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)=C1 LFNXCUNDYSYVJY-UHFFFAOYSA-N 0.000 description 1
- WXAZIUYTQHYBFW-UHFFFAOYSA-N tris(4-methylphenyl)phosphane Chemical compound C1=CC(C)=CC=C1P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 WXAZIUYTQHYBFW-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- 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
-
- 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/38—Esters containing sulfur
- C08F220/382—Esters containing sulfur and containing oxygen, e.g. 2-sulfoethyl (meth)acrylate
-
- 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
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
-
- 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
- G02B1/10—Optical coatings produced by application to, or surface treatment of, optical elements
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerization Catalysts (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Abstract
Description
R200およびR201は、独立して、H、C1〜18アルキル、C3〜C12シクロアルキル、C6〜C14アリール、C1〜C14ヘテロアリール、C7〜C15アラルキル、C2〜C14ヘテロアラルキル、シアノであり、あるいはR200およびR201は、それらが結合している炭素と一緒に、単環式もしくは多環式C3〜C18炭素環または単環式もしくは多環式C1〜C18複素環を形成し;
R202およびR203は、独立して、C1〜C18アルキル、C3〜C12シクロアルキル、C6〜C14アリール、C1〜C18アルキルで1回もしくは2回以上置換されているC6〜C14アリール;C7〜C15アラルキル、(CH3)3Si−であり;あるいはR202およびR203は、C1〜C18アルキル、C3〜C12シクロアルキル、C6〜C14アリール、C7〜C15アラルキルであり、あるいは、
R202およびR203は、C1〜C18アルキル、(C1〜C18アルキルアミノ、ビス(C1〜C18アルキル)アミノ、トリス(C1〜C11アルキル)アンモニウムから選択されるOもしくはN含有基が導入または該OもしくはN含有基で置換されている)C3〜C12シクロアルキルであり、
nが1の場合、R204は、H、C1〜C18アルキル、C3〜C12シクロアルキル、C7〜C14アラルキル、C6〜C14アリール、または以下のアシル:
−C(=O)−H、−C(=O)−C1〜C18アルキル、−C(=O)−C2〜C18アルケニル、−C(=O)−C8〜C14アリール、−C(=O)−C2〜C18アルケニル−C6〜C14アリール、−C(=O)−O−C1〜C18アルキル、−C(=O)−O−C6〜C14アリール、−C(=O)−NH−C1〜C18アルキル、−C(=O)−NH−C6〜C14アリール、および−C(=O)−N(C1〜C18アルキル)2;
からなる群より選択されるアシルであり;あるいは、
nが1の場合、R202およびR204は、それらが結合している窒素原子と一緒に、さらなるヘテロ原子を含有していてもよい5〜12員環を形成し、
nが1を超える場合、R204は、ジ−、トリ−、テトラ−C−i−C−isアルキリデン、ジアシル、トリアシル、またはテトラアシル、およびそれらの塩である]を有する。
実施例1
工程A
N2下における50mLの丸底フラスコに、シクロヘキサノンオキシム(2.87g、25.3mmol)およびテトラヒドロフラン(THF)(15mL)を加えた。発熱を調節するためにフラスコの丸底を室温の水浴に浸け(しかし、発熱は認められなかった)、ジイソプロピルカルボジイミド(3.8g、30.1mmol)を加え、すぐに、砕いたNaOH(0.1g、2.5mmol)を加えた。結果として得られる溶液を、室温の水浴において、マグネチックスターラーを用いて6時間撹拌したところ、いくつかの部分において濁りが生じた。当該混合物を、ブフナー漏斗とワットマン#4ろ紙を用いてろ過した。結果として得られる混合物を4℃に冷却した後、ろ過し、減圧下で濃縮して、淡黄色の固体(3.27g)を得た。NMRは、当該生成物が1,3−ジイソプロピル−O−(N−シクロヘキシリデンアミノ)−イソ尿素に一致する構造を有することを示した。
20mLのガラス製シンチレーションバイアルに、0.45μmシリンジフィルターを通してろ過したチオグリシジルメタクリレート100質量部、N−メチルイミダゾール1部、および工程Aの生成物1部を加えた。当該成分を、均一な溶液が得られるまで、室温で混合しおよび/または超音波浴に入れた。当該混合物を、3mm厚の注入量に対して適切な直径を有するガラスシート鋳型に注入した。鋳型中の混合物を、オーブンにおいて22時間かけて一定の速度で30℃から110℃まで昇温して硬化させ、続いて2時間かけて一定の速度で85℃まで冷却し、脱型した。
1,3−ジイソプロピル−O−(N−シクロヘキシリデンアミノ)−イソ尿素1部の代わりに、1,1,3,3−テトラメチルブチルペルオキシ−2−エチルヘキサノエートであることが報告されているTRIGONOX(登録商標)421重合開始剤1部を使用することを除いて、実施例1の工程Bの手順に従った。
N−メチルイミダゾール1部の代わりにテトラブチルホスホニウムブロミド1部を使用し、1,3−ジイソプロピル−O−(N−シクロヘキシリデンアミノ)−イソ尿素を1.0部ではなく1.5部使用することを除いて、実施例1の工程Bの手順に従った。
1,3−ジイソプロピル−O−(N−シクロヘキシリデンアミノ)−イソ尿素1.5部の代わりにTRIGONOX(登録商標)421を0.8部使用することを除いて、実施例2の手順に従った。
ろ過済みのチオグリシジルメタクリレート90部、ビス−(β−エピチオプロピル)スルフィド10部、三フッ化ホウ素ジエチルエーテル1部、および1,3−ジイソプロピル−O−(N−シクロヘキシリデンアミノ)−イソ尿素1部を使用したことを除いて、実施例1の工程Bの手順に従った。
1,3−ジイソプロピル−O−(N−シクロヘキシリデンアミノ)−イソ尿素1部の代わりにTRIGONOX(登録商標)421を1部使用したことを除いて、実施例3の手順に従った。
ろ過済みチオグリシジルメタクリレート41.7部、4,4−イソプロピリデンジフェノール−ジ(2,3−エピチオプロピル)エーテル41.7部、メチルメタクリレート12.5部、ブチルアクリレート4.17部、および1,3−ジイソプロピル−O−(N−シクロヘキシリデンアミノ)−イソ尿素1部を使用したことを除いて、実施例1の工程Bの手順に従った。
1,3−ジイソプロピル−O−(N−シクロヘキシリデンアミノ)−イソ尿素1部の代わりにTRIGONOX(登録商標)421を1部使用したことを除いて、実施例4の手順に従った。
ろ過済みチオグリシジルメタクリレート46.5部、4,4−イソプロピリデンジフェノール−ジ(2,3−エピチオプロピル)エーテル46.5部、メチルメタクリレート4.7部、ブチルアクリレート2.3部、テトラブチルホスホニウムブロミド1部、および1,3−ジイソプロピル−O−(N−シクロヘキシリデンアミノ)−イソ尿素1部を使用したことを除いて、実施例1の工程Bの手順に従った。
1,3−ジイソプロピル−O−(N−シクロヘキシリデンアミノ)−イソ尿素1部の代わりにTRIGONOX(登録商標)421を0.6部使用したことを除いて、実施例5の手順に従った。
1,3−ジイソプロピル−O−(N−シクロヘキシリデンアミノ)−イソ尿素を1部ではなく1.25部使用したことを除いて、実施例5の手順に従った。
1,3−ジイソプロピル−O−(N−シクロヘキシリデンアミノ)−イソ尿素1部の代わりにTRIGONOX(登録商標)421を0.8部使用したことを除いて、実施例5の手順に従った。
1,3−ジイソプロピル−O−(N−シクロヘキシリデンアミノ)−イソ尿素1部の代わりに、2,5−ジメチル−2,5−ジ−(2−エチルヘキサノイルペルオキシ)ヘキサンであることが報告されているLUPEROX(登録商標)256重合開始剤0.8部を使用したことを除いて、実施例5の手順に従った。
窒素雰囲気下に置かれた、マグネチックスターラーを備える50mLの三ツ口丸底フラスコに、n−ブチルメタクリレート12.85g(100mmol)およびLUPEROX(登録商標)256を444mg(1mmol)加えた。当該フラスコを、平衡状態で80℃に維持された水浴に浸した。5時間後、粘性となった当該混合物を酢酸n−ブチルに溶解させた。固形物濃度を、26.5質量%に調節した。本明細書に記載されるパーセント固形物は、110℃での1時間の加熱の前後に試料を秤量して特定し、加熱前に測定した初期質量の百分率として残留質量を報告した。
工程A
N2下の50mL丸底フラスコに、シクロヘキサノンオキシム(6.56g、49.9mmol)およびTHF(30mL)を加えた。ジシクロヘキシルカルボジイミド(11.34g、55.0mmol)を加え、すぐに粉砕したNaOH(0.2g、5mmol)を加えた。結果として得られる溶液を、室温で4時間撹拌したところ、赤褐色になり、いくつかの部分において濁りが生じた。ジクロロメタン(25mL)を加え、その結果として得られる混合物をろ過し、濃縮した。結果として得られる液体残留物にアセトニトリル(25mL)を加え、当該懸濁液を30分間激しく撹拌した。結果として得られる上層をデカントして廃棄し、残留物をジクロロメタンで希釈し、ろ過し、濃縮し、オレンジ色の油(8.73g)を得た。NMRは、当該生成物が1,3−ジシクロヘキシル−O−(N−シクロヘキシリデンアミノ)−イソ尿素に一致する構造を有することを示した。
LUPEROX(登録商標)256の代わりに工程Aの生成物(319mg(1mmol))を使用したことを除いて、CE−8の手順に従った。
重合後に、結果として得られる材料をn−酢酸ブチルおよびテトラヒドロフラン(THF)の1:1(質量ベース)混合物に溶解させて22.2%固形物に調節したことを除き、CE−8の手順に従った。
LUPEROX(登録商標)256の代わりに1,3−ジイソプロピル−O−(N−シクロヘキシリデンアミノ)−イソ尿素240mg(1mmol)を使用し、結果として得られる材料を、重合後にCE−10の手順に従って処理したことを除き、CE−8の手順に従った。
LUPEROX(登録商標)256の代わりにTRIGONOX(登録商標)421を222mg(0.5mmol)使用し、重合後、結果として得られる材料をTHFに溶解させて、20%固形物に調節したことを除き、CE−8の手順に従った。
LUPEROX(登録商標)256の代わりに1,3−ジイソプロピル−O−(N−シクロヘキシリデンアミノ)−イソ尿素120mg(0.5mmol)を使用し、結果として得られた材料を、重合後、CE−12の手順に従って処理したことを除き、CE−8の手順に従った。
実施例1〜6およびCE1〜7の重合生成物シート試料を、フィッシャー微小硬度(FMH)、屈折率、および黄色度について試験し、その結果を第1表に報告する。CE−8〜13の粘性液体重合生成物試料を、分子量および黄色度について試験し、その結果を第2表に報告する。
Claims (22)
- (a)β−エピチオプロピル官能基を有する少なくとも1種のエチレン性不飽和モノマーを含むモノマー組成物と、
(b)場合により、2つ以上のβ−エピチオプロピル官能基を有するが重合可能なエチレン性不飽和基は有しない化合物と、
(c)イソ尿素官能性重合開始剤と、
(d)前記β−エピチオプロピル官能基間の反応に作用するのに十分な量において存在する触媒と
を含む重合可能な組成物。 - 重合および重合生成物の形成において、前記重合生成物が、前記イソ尿素官能性重合開始剤および前記触媒を含有しない同様の重合可能な組成物と比べて、低減された黄変を示す、請求項1に記載の重合可能な組成物。
- β−エピチオプロピル官能基を有する前記エチレン性不飽和モノマーがチオグリシジルメタクリレートを含む、請求項1に記載の重合可能な組成物。
- 前記チオグリシジルメタクリレートが、グリシジルメタクリレートおよびチオ尿素を含む反応組成物の反応生成物として、前記重合可能な組成物内において形成される、請求項3に記載の重合可能な組成物。
- 前記モノマー組成物(a)がさらに、少なくとも1種の異なる重合可能なエチレン性不飽和モノマーを含む、請求項1に記載の重合可能な組成物。
- 前記異なる重合可能なエチレン性不飽和モノマーが、スチレン、アルキルアクリレート、およびアルキルメタクリレートのうちの少なくとも1つを含む、請求項5に記載の重合可能な組成物。
- 2つ以上のβ−エピチオプロピル官能基を有するが重合可能なエチレン性不飽和基は有しない前記化合物(b)が、前記重合可能な組成物中に存在し、ならびに、2,2−ビス(4−グリシジルオキシフェニル)プロパンおよびチオ尿素を含む反応組成物の反応生成物として前記重合可能な組成物内において形成される、請求項1に記載の重合可能な組成物。
- 前記2,2−ビス(4−グリシジルオキシフェニル)プロパンが、2,2−ビス(4−ヒドロキシフェニル)プロパンおよびエピクロロヒドリンを含む反応組成物の反応生成物である、請求項7に記載の重合可能な組成物。
- 前記イソ尿素官能性重合開始剤(c)が、O−ジアルキルアミノ−イソ尿素およびO−イミノ−イソ尿素のうちの少なくとも1つを含む、請求項1に記載の重合可能な組成物。
- 請求項2に記載の重合可能な組成物の重合生成物。
- 請求項10に記載の重合生成物を含む光学素子。
- 前記触媒(d)が、1,4−ジアザビシクロ[2.2.2]オクタン、複素環を有するアミン、ホスフィン、第四級アンモニウム塩、第四級ホスホニウム塩、第三級スルホニウム塩、第二級ヨードニウム塩、三ハロゲン化ホウ素およびそれらの錯体、有機酸およびそれらのエステル、ならびに金属ハロゲン化物、のうちの少なくとも1つを含む、請求項1に記載の重合可能な組成物。
- 付加重合によって製造される硫黄含有重合生成物の黄色度を低減する方法であって、イソ尿素官能性重合開始剤およびβ−エピチオプロピル官能基間の反応に作用する触媒の存在下において、
(a)β−エピチオプロピル官能基を有する少なくとも1種のエチレン性不飽和モノマーを含むモノマー組成物と、場合により、
(b)2つ以上のβ−エピチオプロピル官能基を有するが重合可能なエチレン性不飽和基は有しない化合物と
を含む重合可能な組成物を反応させる工程を含む、方法。 - 重合および重合生成物の形成において、前記重合生成物が、前記イソ尿素官能性重合開始剤および前記触媒を含有しない同様の重合可能な組成物と比べて、低減された黄変を示す、請求項13に記載の方法。
- β−エピチオプロピル官能基を有する前記エチレン性不飽和モノマーがチオグリシジルメタクリレートを含む、請求項13に記載の方法。
- 前記チオグリシジルメタクリレートが、グリシジルメタクリレートおよびチオ尿素を含む反応組成物の反応生成物として、前記重合可能な組成物内において形成される、請求項15に記載の方法。
- 前記モノマー組成物(a)がさらに、少なくとも1種の異なる重合可能なエチレン性不飽和モノマーを含む、請求項13に記載の方法。
- 前記異なる重合可能なエチレン性不飽和モノマーが、スチレン、アルキルメタクリレート、およびアルキルアクリレートのうちの少なくとも1つを含む、請求項17に記載の方法。
- 2つ以上のβ−エピチオプロピル官能基を有するが重合可能なエチレン性不飽和基は有しない前記化合物(b)が、前記重合可能な組成物中に存在し、ならびに、2,2−ビス(4−グリシジルオキシフェニル)プロパンおよびチオ尿素を含む反応組成物の反応生成物として前記重合可能な組成物内において形成される、請求項13に記載の方法。
- 前記2,2−ビス(4−グリシジルオキシフェニル)プロパンが、2,2−ビス(4−ヒドロキシフェニル)プロパンおよびエピクロロヒドリンを含む反応組成物の反応生成物である、請求項19に記載の方法。
- 前記イソ尿素官能性重合開始剤(c)が、O−ジアルキルアミノ−イソ尿素およびO−イミノ−イソ尿素のうちの少なくとも1つを含む、請求項13に記載の方法。
- 前記触媒が、1,4−ジアザビシクロ[2.2.2]オクタン、複素環を有するアミン、ホスフィン、第四級アンモニウム塩、第四級ホスホニウム塩、第三級スルホニウム塩、第二級ヨードニウム塩、三ハロゲン化ホウ素およびそれらの錯体、有機酸およびそれらのエステル、ならびに金属ハロゲン化物、のうちの少なくとも1つを含む、請求項13に記載の方法。
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JPS52142793A (en) * | 1976-05-21 | 1977-11-28 | Thomson Csf | Electron functional resin |
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JP2004043826A (ja) * | 2003-11-04 | 2004-02-12 | Mitsui Chemicals Inc | (チオ)エポキシ系重合性組成物 |
JP2009074032A (ja) * | 2007-08-31 | 2009-04-09 | Mitsubishi Gas Chem Co Inc | 光学材料用樹脂組成物 |
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