JP2013079368A - 組成物及び重合物 - Google Patents
組成物及び重合物 Download PDFInfo
- Publication number
- JP2013079368A JP2013079368A JP2012195180A JP2012195180A JP2013079368A JP 2013079368 A JP2013079368 A JP 2013079368A JP 2012195180 A JP2012195180 A JP 2012195180A JP 2012195180 A JP2012195180 A JP 2012195180A JP 2013079368 A JP2013079368 A JP 2013079368A
- Authority
- JP
- Japan
- Prior art keywords
- carbonate
- bis
- compound
- episulfide
- butyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 184
- 229920000642 polymer Polymers 0.000 title claims abstract description 47
- -1 carbonate compound Chemical class 0.000 claims abstract description 592
- 229910052796 boron Inorganic materials 0.000 claims abstract description 113
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims abstract description 112
- 150000001875 compounds Chemical class 0.000 claims description 167
- 239000000126 substance Substances 0.000 claims description 127
- 150000003553 thiiranes Chemical group 0.000 claims description 111
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 34
- 125000001931 aliphatic group Chemical group 0.000 claims description 31
- 125000000524 functional group Chemical group 0.000 claims description 28
- 125000004122 cyclic group Chemical group 0.000 claims description 26
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 24
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 24
- 230000000379 polymerizing effect Effects 0.000 claims description 20
- 238000004519 manufacturing process Methods 0.000 claims description 16
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 15
- 150000003568 thioethers Chemical group 0.000 claims description 15
- 125000005587 carbonate group Chemical group 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 229910015900 BF3 Inorganic materials 0.000 claims description 12
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 claims description 10
- 238000010438 heat treatment Methods 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 238000006116 polymerization reaction Methods 0.000 abstract description 55
- 238000007086 side reaction Methods 0.000 abstract description 20
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 244
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 234
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 187
- 239000007983 Tris buffer Substances 0.000 description 158
- 229960004063 propylene glycol Drugs 0.000 description 84
- 235000013772 propylene glycol Nutrition 0.000 description 83
- 239000004593 Epoxy Substances 0.000 description 82
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 68
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 66
- 229940035437 1,3-propanediol Drugs 0.000 description 66
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 66
- 238000000034 method Methods 0.000 description 63
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 61
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 61
- 239000000047 product Substances 0.000 description 55
- 235000011187 glycerol Nutrition 0.000 description 54
- PDXRQENMIVHKPI-UHFFFAOYSA-N cyclohexane-1,1-diol Chemical compound OC1(O)CCCCC1 PDXRQENMIVHKPI-UHFFFAOYSA-N 0.000 description 46
- FNTHQRXVZDCWSP-UHFFFAOYSA-N cyclohexane-1,1,2-triol Chemical compound OC1CCCCC1(O)O FNTHQRXVZDCWSP-UHFFFAOYSA-N 0.000 description 44
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 43
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 40
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 39
- 239000012986 chain transfer agent Substances 0.000 description 39
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 37
- 238000006243 chemical reaction Methods 0.000 description 37
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 36
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 36
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 31
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 30
- 239000001294 propane Substances 0.000 description 30
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 29
- CXHHBNMLPJOKQD-UHFFFAOYSA-M methyl carbonate Chemical compound COC([O-])=O CXHHBNMLPJOKQD-UHFFFAOYSA-M 0.000 description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- 150000002148 esters Chemical class 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 26
- 238000005160 1H NMR spectroscopy Methods 0.000 description 24
- PIZLBWGMERQCOC-UHFFFAOYSA-N dibenzyl carbonate Chemical compound C=1C=CC=CC=1COC(=O)OCC1=CC=CC=C1 PIZLBWGMERQCOC-UHFFFAOYSA-N 0.000 description 24
- 238000005259 measurement Methods 0.000 description 24
- 229940043375 1,5-pentanediol Drugs 0.000 description 22
- LCLOXRAKDJBSMN-UHFFFAOYSA-N pentyl hydrogen carbonate Chemical compound CCCCCOC(O)=O LCLOXRAKDJBSMN-UHFFFAOYSA-N 0.000 description 22
- 238000005481 NMR spectroscopy Methods 0.000 description 21
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 21
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 21
- WCVRQHFDJLLWFE-UHFFFAOYSA-N pentane-1,2-diol Chemical compound CCCC(O)CO WCVRQHFDJLLWFE-UHFFFAOYSA-N 0.000 description 21
- 229940051250 hexylene glycol Drugs 0.000 description 20
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 19
- FRJZOYQRAJDROR-UHFFFAOYSA-N cyclohexyl hydrogen carbonate Chemical compound OC(=O)OC1CCCCC1 FRJZOYQRAJDROR-UHFFFAOYSA-N 0.000 description 19
- GECNIOWBEXHZNM-UHFFFAOYSA-N hexyl hydrogen carbonate Chemical compound CCCCCCOC(O)=O GECNIOWBEXHZNM-UHFFFAOYSA-N 0.000 description 19
- 239000000243 solution Substances 0.000 description 19
- 150000005846 sugar alcohols Polymers 0.000 description 19
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical class CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 18
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 18
- 239000001257 hydrogen Substances 0.000 description 18
- 229910052739 hydrogen Inorganic materials 0.000 description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 17
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 17
- 238000011156 evaluation Methods 0.000 description 17
- 239000000463 material Substances 0.000 description 17
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 17
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 16
- GTTSNKDQDACYLV-UHFFFAOYSA-N Trihydroxybutane Chemical compound CCCC(O)(O)O GTTSNKDQDACYLV-UHFFFAOYSA-N 0.000 description 16
- XHGJOIDWPAJLHO-UHFFFAOYSA-N heptyl hydrogen carbonate Chemical compound CCCCCCCOC(O)=O XHGJOIDWPAJLHO-UHFFFAOYSA-N 0.000 description 16
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 16
- RZKVHIPRDKHSAJ-UHFFFAOYSA-N octyl hydrogen carbonate Chemical compound CCCCCCCCOC(O)=O RZKVHIPRDKHSAJ-UHFFFAOYSA-N 0.000 description 16
- 150000002430 hydrocarbons Chemical group 0.000 description 15
- 229910052757 nitrogen Inorganic materials 0.000 description 15
- FVGBHSIHHXTYTH-UHFFFAOYSA-N pentane-1,1,1-triol Chemical compound CCCCC(O)(O)O FVGBHSIHHXTYTH-UHFFFAOYSA-N 0.000 description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 15
- 239000011593 sulfur Substances 0.000 description 15
- 229910052717 sulfur Inorganic materials 0.000 description 15
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 14
- UXXXZMDJQLPQPH-UHFFFAOYSA-N bis(2-methylpropyl) carbonate Chemical compound CC(C)COC(=O)OCC(C)C UXXXZMDJQLPQPH-UHFFFAOYSA-N 0.000 description 14
- 239000001273 butane Substances 0.000 description 14
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 14
- TZMQHOJDDMFGQX-UHFFFAOYSA-N hexane-1,1,1-triol Chemical compound CCCCCC(O)(O)O TZMQHOJDDMFGQX-UHFFFAOYSA-N 0.000 description 14
- 238000012986 modification Methods 0.000 description 14
- 230000004048 modification Effects 0.000 description 14
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 14
- 229920003986 novolac Polymers 0.000 description 14
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 13
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 13
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 13
- 238000000576 coating method Methods 0.000 description 13
- VTRGQZOKQCSGAD-UHFFFAOYSA-M decyl carbonate Chemical compound CCCCCCCCCCOC([O-])=O VTRGQZOKQCSGAD-UHFFFAOYSA-M 0.000 description 13
- 238000004821 distillation Methods 0.000 description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
- 239000002994 raw material Substances 0.000 description 13
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical class ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 12
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical class CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 12
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 12
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- 150000001412 amines Chemical class 0.000 description 12
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 12
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 12
- DFFDSQBEGQFJJU-UHFFFAOYSA-M butyl carbonate Chemical compound CCCCOC([O-])=O DFFDSQBEGQFJJU-UHFFFAOYSA-M 0.000 description 12
- 239000011248 coating agent Substances 0.000 description 12
- VUPKGFBOKBGHFZ-UHFFFAOYSA-N dipropyl carbonate Chemical compound CCCOC(=O)OCCC VUPKGFBOKBGHFZ-UHFFFAOYSA-N 0.000 description 12
- SXCBDZAEHILGLM-UHFFFAOYSA-N heptane-1,7-diol Chemical compound OCCCCCCCO SXCBDZAEHILGLM-UHFFFAOYSA-N 0.000 description 12
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 12
- FTGXUUMZWOZYGD-UHFFFAOYSA-N nonyl hydrogen carbonate Chemical compound CCCCCCCCCOC(O)=O FTGXUUMZWOZYGD-UHFFFAOYSA-N 0.000 description 12
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 12
- FOWDZVNRQHPXDO-UHFFFAOYSA-N propyl hydrogen carbonate Chemical compound CCCOC(O)=O FOWDZVNRQHPXDO-UHFFFAOYSA-N 0.000 description 12
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical class ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 12
- RWLALWYNXFYRGW-UHFFFAOYSA-N 2-Ethyl-1,3-hexanediol Chemical compound CCCC(O)C(CC)CO RWLALWYNXFYRGW-UHFFFAOYSA-N 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- QLVWOKQMDLQXNN-UHFFFAOYSA-N dibutyl carbonate Chemical compound CCCCOC(=O)OCCCC QLVWOKQMDLQXNN-UHFFFAOYSA-N 0.000 description 11
- 229960005082 etohexadiol Drugs 0.000 description 11
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 11
- 229910052751 metal Inorganic materials 0.000 description 11
- 239000002184 metal Substances 0.000 description 11
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 11
- 125000001424 substituent group Chemical group 0.000 description 11
- 125000003944 tolyl group Chemical group 0.000 description 11
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 10
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- 239000003963 antioxidant agent Substances 0.000 description 10
- 235000006708 antioxidants Nutrition 0.000 description 10
- 239000012298 atmosphere Substances 0.000 description 10
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 10
- YEVXZVJTSQWZDM-UHFFFAOYSA-N cyclobutyl hydrogen carbonate Chemical compound OC(=O)OC1CCC1 YEVXZVJTSQWZDM-UHFFFAOYSA-N 0.000 description 10
- ZOCHHNOQQHDWHG-UHFFFAOYSA-N hexan-3-ol Chemical compound CCCC(O)CC ZOCHHNOQQHDWHG-UHFFFAOYSA-N 0.000 description 10
- 238000002156 mixing Methods 0.000 description 10
- JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 description 10
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 10
- 150000002989 phenols Chemical class 0.000 description 10
- 229920001296 polysiloxane Chemical class 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical class C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical class CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
- 239000012299 nitrogen atmosphere Substances 0.000 description 9
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
- 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 9
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical class C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 9
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 8
- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 8
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 8
- 239000004215 Carbon black (E152) Substances 0.000 description 8
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 8
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 8
- 239000000853 adhesive Substances 0.000 description 8
- 230000001070 adhesive effect Effects 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 8
- RSYNHXZMASRGMC-UHFFFAOYSA-N butan-2-yl hydrogen carbonate Chemical compound CCC(C)OC(O)=O RSYNHXZMASRGMC-UHFFFAOYSA-N 0.000 description 8
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 8
- 238000005260 corrosion Methods 0.000 description 8
- AVOZEJJQAGFSRD-UHFFFAOYSA-N cyclopentyl hydrogen carbonate Chemical compound OC(=O)OC1CCCC1 AVOZEJJQAGFSRD-UHFFFAOYSA-N 0.000 description 8
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 8
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 8
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 8
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 8
- 229930195733 hydrocarbon Natural products 0.000 description 8
- 239000010410 layer Substances 0.000 description 8
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- AVKNGPAMCBSNSO-UHFFFAOYSA-N cyclohexylmethanamine Chemical compound NCC1CCCCC1 AVKNGPAMCBSNSO-UHFFFAOYSA-N 0.000 description 1
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- MGAWZIGLGCWZMC-UHFFFAOYSA-N cyclopentyl docosyl carbonate Chemical compound C(OC1CCCC1)(OCCCCCCCCCCCCCCCCCCCCCC)=O MGAWZIGLGCWZMC-UHFFFAOYSA-N 0.000 description 1
- VASAHPKZSLTHKB-UHFFFAOYSA-N cyclopentyl dodecyl carbonate Chemical compound C(OC1CCCC1)(OCCCCCCCCCCCC)=O VASAHPKZSLTHKB-UHFFFAOYSA-N 0.000 description 1
- SDZJWCYJDQIDAU-UHFFFAOYSA-N cyclopentyl ethyl carbonate Chemical compound CCOC(=O)OC1CCCC1 SDZJWCYJDQIDAU-UHFFFAOYSA-N 0.000 description 1
- HVLGJEJBHKXDJC-UHFFFAOYSA-N cyclopentyl heptadecyl carbonate Chemical compound C(OC1CCCC1)(OCCCCCCCCCCCCCCCCC)=O HVLGJEJBHKXDJC-UHFFFAOYSA-N 0.000 description 1
- CQUHCHRVISPWOI-UHFFFAOYSA-N cyclopentyl heptyl carbonate Chemical compound C(OC1CCCC1)(OCCCCCCC)=O CQUHCHRVISPWOI-UHFFFAOYSA-N 0.000 description 1
- KACRGDCHEXPGOL-UHFFFAOYSA-N cyclopentyl hexacosyl carbonate Chemical compound C(OC1CCCC1)(OCCCCCCCCCCCCCCCCCCCCCCCCCC)=O KACRGDCHEXPGOL-UHFFFAOYSA-N 0.000 description 1
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- ZFUQGJPCODCGDO-UHFFFAOYSA-N cyclopentyl methyl carbonate Chemical compound COC(=O)OC1CCCC1 ZFUQGJPCODCGDO-UHFFFAOYSA-N 0.000 description 1
- ULEFNQDTCZTECX-UHFFFAOYSA-N cyclopentyl nonadecyl carbonate Chemical compound C(OC1CCCC1)(OCCCCCCCCCCCCCCCCCCC)=O ULEFNQDTCZTECX-UHFFFAOYSA-N 0.000 description 1
- IPGPQYTXZVISAK-UHFFFAOYSA-N cyclopentyl nonyl carbonate Chemical compound C(OC1CCCC1)(OCCCCCCCCC)=O IPGPQYTXZVISAK-UHFFFAOYSA-N 0.000 description 1
- XNFAPEQUWWBWLJ-UHFFFAOYSA-N cyclopentyl octacosyl carbonate Chemical compound C(OC1CCCC1)(OCCCCCCCCCCCCCCCCCCCCCCCCCCCC)=O XNFAPEQUWWBWLJ-UHFFFAOYSA-N 0.000 description 1
- PWDQRAPWIIYEAW-UHFFFAOYSA-N cyclopentyl octadecyl carbonate Chemical compound C(OC1CCCC1)(OCCCCCCCCCCCCCCCCCC)=O PWDQRAPWIIYEAW-UHFFFAOYSA-N 0.000 description 1
- GAXPIVJMFUCMKK-UHFFFAOYSA-N cyclopentyl octyl carbonate Chemical compound C(OC1CCCC1)(OCCCCCCCC)=O GAXPIVJMFUCMKK-UHFFFAOYSA-N 0.000 description 1
- UJSKZHNCXXHGAJ-UHFFFAOYSA-N cyclopentyl pentadecyl carbonate Chemical compound C(OC1CCCC1)(OCCCCCCCCCCCCCCC)=O UJSKZHNCXXHGAJ-UHFFFAOYSA-N 0.000 description 1
- MLELRGXIKJUWHW-UHFFFAOYSA-N cyclopentyl phenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1CCCC1 MLELRGXIKJUWHW-UHFFFAOYSA-N 0.000 description 1
- SXYWHEDCEPEUAQ-UHFFFAOYSA-N cyclopentyl tetradecyl carbonate Chemical compound C(OC1CCCC1)(OCCCCCCCCCCCCCC)=O SXYWHEDCEPEUAQ-UHFFFAOYSA-N 0.000 description 1
- HPRIZERKANHXPN-UHFFFAOYSA-N cyclopentyl tricosyl carbonate Chemical compound C(OC1CCCC1)(OCCCCCCCCCCCCCCCCCCCCCCC)=O HPRIZERKANHXPN-UHFFFAOYSA-N 0.000 description 1
- VDKXQTYMCBBCKO-UHFFFAOYSA-N cyclopentyl tridecyl carbonate Chemical compound C(OC1CCCC1)(OCCCCCCCCCCCCC)=O VDKXQTYMCBBCKO-UHFFFAOYSA-N 0.000 description 1
- IBSOYCDLKJCGLX-UHFFFAOYSA-N cyclopentyl undecyl carbonate Chemical compound C(OC1CCCC1)(OCCCCCCCCCCC)=O IBSOYCDLKJCGLX-UHFFFAOYSA-N 0.000 description 1
- ZJAPOEKGBGSNBG-UHFFFAOYSA-N cyclopropane-1,1-diol Chemical compound OC1(O)CC1 ZJAPOEKGBGSNBG-UHFFFAOYSA-N 0.000 description 1
- YOXHCYXIAVIFCZ-UHFFFAOYSA-N cyclopropanol Chemical compound OC1CC1 YOXHCYXIAVIFCZ-UHFFFAOYSA-N 0.000 description 1
- QAEWYCNTSLEEQK-UHFFFAOYSA-N cyclopropyl (2,3,4-triethylphenyl) carbonate Chemical compound C(OC1=C(C(=C(C=C1)CC)CC)CC)(OC1CC1)=O QAEWYCNTSLEEQK-UHFFFAOYSA-N 0.000 description 1
- MHZDQHKSMPZVPL-UHFFFAOYSA-N cyclopropyl (2-ethylphenyl) carbonate Chemical compound C(OC1CC1)(OC1=C(C=CC=C1)CC)=O MHZDQHKSMPZVPL-UHFFFAOYSA-N 0.000 description 1
- ZMCUEBJWQZNWGI-UHFFFAOYSA-N cyclopropyl (2-methylphenyl) carbonate Chemical compound C(OC1=C(C=CC=C1)C)(OC1CC1)=O ZMCUEBJWQZNWGI-UHFFFAOYSA-N 0.000 description 1
- CEDVDVFNRTYQCX-UHFFFAOYSA-N cyclopropyl [2-(dimethylamino)phenyl] carbonate Chemical compound C(OC1=C(C=CC=C1)N(C)C)(OC1CC1)=O CEDVDVFNRTYQCX-UHFFFAOYSA-N 0.000 description 1
- CQEDTZKSFSBYFC-UHFFFAOYSA-N cyclopropyl [2-(trifluoromethyl)phenyl] carbonate Chemical compound C(OC1=C(C=CC=C1)C(F)(F)F)(OC1CC1)=O CQEDTZKSFSBYFC-UHFFFAOYSA-N 0.000 description 1
- YIZHLPWIXJQESU-UHFFFAOYSA-N cyclopropyl docosyl carbonate Chemical compound C(OC1CC1)(OCCCCCCCCCCCCCCCCCCCCCC)=O YIZHLPWIXJQESU-UHFFFAOYSA-N 0.000 description 1
- OSYGETFIQZQREV-UHFFFAOYSA-N cyclopropyl dodecyl carbonate Chemical compound C(OC1CC1)(OCCCCCCCCCCCC)=O OSYGETFIQZQREV-UHFFFAOYSA-N 0.000 description 1
- MSGSVADTPZTVSB-UHFFFAOYSA-N cyclopropyl ethyl carbonate Chemical compound CCOC(=O)OC1CC1 MSGSVADTPZTVSB-UHFFFAOYSA-N 0.000 description 1
- BCROBPOTFUIZAN-UHFFFAOYSA-N cyclopropyl heptyl carbonate Chemical compound C(OC1CC1)(OCCCCCCC)=O BCROBPOTFUIZAN-UHFFFAOYSA-N 0.000 description 1
- DUKJZVYWQRQMFO-UHFFFAOYSA-N cyclopropyl hexacosyl carbonate Chemical compound C(OC1CC1)(OCCCCCCCCCCCCCCCCCCCCCCCCCC)=O DUKJZVYWQRQMFO-UHFFFAOYSA-N 0.000 description 1
- WCITXSPTFBHPJO-UHFFFAOYSA-N cyclopropyl hexadecyl carbonate Chemical compound C(OC1CC1)(OCCCCCCCCCCCCCCCC)=O WCITXSPTFBHPJO-UHFFFAOYSA-N 0.000 description 1
- GTJOCKHSTFJMKC-UHFFFAOYSA-N cyclopropyl hexyl carbonate Chemical compound C(OC1CC1)(OCCCCCC)=O GTJOCKHSTFJMKC-UHFFFAOYSA-N 0.000 description 1
- PDYKYDDSTOCDRV-UHFFFAOYSA-N cyclopropyl icosyl carbonate Chemical compound C(OC1CC1)(OCCCCCCCCCCCCCCCCCCCC)=O PDYKYDDSTOCDRV-UHFFFAOYSA-N 0.000 description 1
- ORIOMEQNMRFCMM-UHFFFAOYSA-N cyclopropyl methyl carbonate Chemical compound COC(=O)OC1CC1 ORIOMEQNMRFCMM-UHFFFAOYSA-N 0.000 description 1
- PEJGHFZDWVJZDB-UHFFFAOYSA-N cyclopropyl nonacosyl carbonate Chemical compound C(OC1CC1)(OCCCCCCCCCCCCCCCCCCCCCCCCCCCCC)=O PEJGHFZDWVJZDB-UHFFFAOYSA-N 0.000 description 1
- VLRZYYBGEINOLB-UHFFFAOYSA-N cyclopropyl nonadecyl carbonate Chemical compound C(OC1CC1)(OCCCCCCCCCCCCCCCCCCC)=O VLRZYYBGEINOLB-UHFFFAOYSA-N 0.000 description 1
- PWIFXSOHNDLOCK-UHFFFAOYSA-N cyclopropyl nonyl carbonate Chemical compound C(OC1CC1)(OCCCCCCCCC)=O PWIFXSOHNDLOCK-UHFFFAOYSA-N 0.000 description 1
- PQIGRXGVKFYRJJ-UHFFFAOYSA-N cyclopropyl octacosyl carbonate Chemical compound C(OC1CC1)(OCCCCCCCCCCCCCCCCCCCCCCCCCCCC)=O PQIGRXGVKFYRJJ-UHFFFAOYSA-N 0.000 description 1
- GDPCYUIYSGECFG-UHFFFAOYSA-N cyclopropyl octadecyl carbonate Chemical compound C(OC1CC1)(OCCCCCCCCCCCCCCCCCC)=O GDPCYUIYSGECFG-UHFFFAOYSA-N 0.000 description 1
- WLTXBHSPBFVLMF-UHFFFAOYSA-N cyclopropyl octyl carbonate Chemical compound C(OC1CC1)(OCCCCCCCC)=O WLTXBHSPBFVLMF-UHFFFAOYSA-N 0.000 description 1
- IDINANMXSWDVJW-UHFFFAOYSA-N cyclopropyl pentadecyl carbonate Chemical compound C(OC1CC1)(OCCCCCCCCCCCCCCC)=O IDINANMXSWDVJW-UHFFFAOYSA-N 0.000 description 1
- AGKOHFXTHDNPDQ-UHFFFAOYSA-N cyclopropyl phenyl carbonate Chemical compound C(OC1CC1)(OC1=CC=CC=C1)=O AGKOHFXTHDNPDQ-UHFFFAOYSA-N 0.000 description 1
- USGGIJKPIQSVRN-UHFFFAOYSA-N cyclopropyl propyl carbonate Chemical compound CCCOC(=O)OC1CC1 USGGIJKPIQSVRN-UHFFFAOYSA-N 0.000 description 1
- CUDWYHBTTMZIIV-UHFFFAOYSA-N cyclopropyl tetracosyl carbonate Chemical compound C(OC1CC1)(OCCCCCCCCCCCCCCCCCCCCCCCC)=O CUDWYHBTTMZIIV-UHFFFAOYSA-N 0.000 description 1
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- BUPSRAOWWFHETK-UHFFFAOYSA-N cyclopropyl triacontyl carbonate Chemical compound C(OC1CC1)(OCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC)=O BUPSRAOWWFHETK-UHFFFAOYSA-N 0.000 description 1
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- 125000001165 hydrophobic group Chemical group 0.000 description 1
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- IVBQHPBHCQBSML-UHFFFAOYSA-N icosyl phenyl carbonate Chemical compound CCCCCCCCCCCCCCCCCCCCOC(=O)OC1=CC=CC=C1 IVBQHPBHCQBSML-UHFFFAOYSA-N 0.000 description 1
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- 230000001678 irradiating effect Effects 0.000 description 1
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- MMSLPVXVIHCQKT-UHFFFAOYSA-N propyl (2,3,4-tripropylphenyl) carbonate Chemical compound CCCOC(=O)OC1=CC=C(CCC)C(CCC)=C1CCC MMSLPVXVIHCQKT-UHFFFAOYSA-N 0.000 description 1
- WEONJCQFBSREHQ-UHFFFAOYSA-N propyl (2-propylphenyl) carbonate Chemical compound CCCOC(=O)OC1=CC=CC=C1CCC WEONJCQFBSREHQ-UHFFFAOYSA-N 0.000 description 1
- WESGWJKHQOVRHY-UHFFFAOYSA-N propyl tetradecyl carbonate Chemical compound CCCCCCCCCCCCCCOC(=O)OCCC WESGWJKHQOVRHY-UHFFFAOYSA-N 0.000 description 1
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- 230000035484 reaction time Effects 0.000 description 1
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Landscapes
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Abstract
【解決手段】(A)カーボネート化合物と、(B)三ハロゲン化ホウ素と、(C)エピスルフィド化合物とを含有する組成物、及び該組成物から得られる重合物。
【選択図】なし
Description
[1]
(A)カーボネート化合物と、(B)三ハロゲン化ホウ素と、(C)エピスルフィド化合物と、を含有する組成物。
[2]
前記カーボネート化合物が、下記式(1)で表される化合物である、項[1]記載の組成物。
[式中、aは、1以上の数を示し、R1及びR2は、炭素数1〜33の鎖状、分岐状若しくは環状の脂肪族炭化水素基又は置換若しくは無置換の芳香族炭化水素基を示し、R1及びR2は、互いに連結されていてもよく、aが2以上の場合、複数存在するR2は同一でも異なっていてもよく、R2同士が連結されていてもよい。]
[3]
前記カーボネート化合物の炭素数が、3〜25である、項[1]又は[2]記載の組成物。
[4]
前記カーボネート化合物のカーボネート基の数が、1〜4である、項[1]〜[3]のいずれか一項に記載の組成物。
[5] 前記(A)カーボネート化合物及び前記(B)三ハロゲン化ホウ素の少なくとも一部が錯体を形成している、項[1]〜[4]のいずれか一項に記載の組成物。
[6]
下記式(2)で表される、前記(A)カーボネート化合物と前記(B)三ハロゲン化ホウ素との比率を表す指標αが1〜1000である、項[1]〜[5]のいずれか一項に記載の組成物。
指標α=αc/αb (2)
αc:前記カーボネート化合物のカーボネート基の物質量(mol)
αb:前記三ハロゲン化ホウ素の物質量(mol)
[7]
前記三ハロゲン化ホウ素が、三フッ化ホウ素、三塩化ホウ素、及び三臭化ホウ素からなる群より選ばれる少なくとも1種である、項[1]〜[6]のいずれか一項に記載の組成物。
[8]
前記エピスルフィド化合物が、3員環チオエーテル構造のみを重合性官能基として有する化合物である、項[1]〜[7]のいずれか一項に記載の組成物。
[9]
前記三ハロゲン化ホウ素の物質量(mol)と、前記エピスルフィド化合物に含まれるエピスルフィド基の物質量(mol)との比が、1:10〜1:100000である、項[1]〜[8]のいずれか一項に記載の組成物。
[10]
前記エピスルフィド化合物のエピスルフィド当量が、65〜700g/molである、項[1]〜[9]のいずれか一項に記載の組成物。
[11]
前記エピスルフィド化合物が、下記式(3)、(4)、(5)又は(6)で表される部分構造を有する、項[1]〜[10]のいずれか一項に記載の組成物。
[式中、R20、R21、R22、R23、R24、R25、R26、R27、R28、R29、R30、R31、R32、R33及びR34はそれぞれ独立に、水素原子又は炭素数1〜20の鎖状、分岐状若しくは環状の脂肪族炭化水素基又は置換若しくは無置換の芳香族炭化水素基を示す。]
[12]
項[1]〜[11]のいずれか一項に記載の組成物中の前記エピスルフィド化合物を重合して形成される、重合物。
[13]
項[1]〜[11]のいずれか一項に記載の組成物中の前記エピスルフィド化合物を加熱及び/又はエネルギー線照射により重合する、重合物を製造する方法。
本実施形態に係る組成物は、(A)カーボネート化合物(以下、場合により「成分(A)」という)と、(B)三ハロゲン化ホウ素(以下、場合により「成分(B)」という)と、(C)エピスルフィド化合物(以下、場合により「成分(C)」という)と、を含有する。以下、組成物に含有される成分(A)、(B)及び(C)並びにその他の成分の詳細について説明する。
本実施形態の成分(A)は、カーボネート基を分子内に1つ以上有するカーボネート化合物である。成分(A)として、1種のカーボネート化合物を単独で用いてもよいし、複数種のカーボネート化合物を組み合わせて用いてもよい。
本実施形態に係る脂肪族単官能カーボネート化合物は、カーボネート基を1つ有し、脂肪族炭化水素基のみを有するものであれば、特に限定されない。脂肪族単官能カーボネート化合物は、上記式(1)において、aが1であり、R1及びR2が脂肪族炭化水素基で表される化合物が挙げられる。
本実施形態に係る芳香族単官能カーボネート化合物は、カーボネート基を1つ有し、芳香族炭化水素基を1つ以上有するものであれば、特に限定されない。芳香族単官能カーボネート化合物は、上記式(1)において、aが1であり、R1及び/又はR2が芳香族炭化水素基で表される化合物が挙げられる。
本実施形態に係る多官能カーボネート化合物は、カーボネート基を2つ以上有するものであれば、特に限定されない。多官能カーボネート化合物は、上記式(1)において、aが2以上で表される化合物が挙げられる。
本実施形態の(B)三ハロゲン化ホウ素は、ハロゲン原子3個とホウ素原子1個とから構成されている化合物である。
本実施形態の成分(C)は、重合性官能基として、3員環チオエーテル構造を少なくとも1つ以上有する化合物である。成分(C)として、1種のエピスルフィド化合物を単独で用いてもよいし、複数種のエピスルフィド化合物を組み合わせて用いてもよい。
単官能エピスルフィド化合物は、3員環チオエーテル構造を1つ有する化合物であれば特に限定されるものではなく、具体的には、エチレンスルフィド、プロピレンスルフィド、1−ブテンスルフィド、2−ブテンスルフィド、ブタジエンスルフィド、ブタジエンジチオエポキシド、シクロブテンスルフィド、1,3−シクロブタジエンジチオエポキシド、1−ペンテンスルフィド、2−ペンテンスルフィド、1,3−ペンタジエンジチオエポキシド、1,4−ペンタジエンジチオエポキシド、2−メチル−2−ブテンスルフィド、2−メチル−3−ブテンスルフィド、シクロペンテンスルフィド、1,3−シクロペンタジエンジチオエポキシド、1−メチル−シクロブテンスルフィド、3−メチル−1−シクロブテンスルフィド、1−ヘキセンスルフィド、2−ヘキセンスルフィド、3−ヘキセンスルフィド、1,3−ヘキサジエンジチオエポキシド、1,4−ヘキサジエンジチオエポキシド、1,5−ヘキサジエンジチオエポキシド、1,3,5−ヘキサトリエントリチオエポキシド、シクロヘキセンスルフィド、1,3−シクロヘキサジエンジチオエポキシド、1,3,5−シクロヘキサトリエントリチオエポキシド、1−メチル−シクロペンテンスルフィド、3−メチル−シクロペンテンスルフィド、1−メチル−1,3−シクロペンタジエンジチオエポキシド、2−メチル−1,3−シクロペンタジエンジチオエポキシド、5−メチル−1,3−シクロペンタジエンジチオエポキシド、3,4−ジメチル−シクロブテンスルフィド、2,3−ジメチル−シクロブテンスルフィド、1,2−ジメチル−シクロブテンスルフィド、1,2−ジメチル−1,3−シクロブタジエンジチオエポキシド、2,3−ジメチル−1,3−シクロブタジエンジチオエポキシド、3,3−ジメチル−1,2−チオエポキシブタン、1−ヘプテンスルフィド、2−ヘプテンスルフィド、3−ヘプテンスルフィド、1,3−ヘプタジエンジチオエポキシド、1,4−ヘプタジエンジチオエポキシド、1,5−ヘプタジエンジチオエポキシド、1,5−ヘプタジエンジチオエポキシド、1,6−ヘプタジエンジチオエポキシド、1,3,5−ヘプタトリエントリチオエポキシド、1,3,6−ヘプタトリエントリチオエポキシド、1,4,6−ヘプタトリエントリチオエポキシド、シクロヘプテンスルフィド、1−メチル−シクロヘキセンスルフィド、3−メチル−シクロヘキセンスルフィド、4−メチル−シクロヘキセンスルフィド、1−メチル−1,3−シクロヘキサジエンジチオエポキシド、1−メチル−1,4−ヘキサジエンジチオエポキシド、1−メチル−1,3,5−ヘキサトリエントリチオエポキシド、1,2−チオエポキシ−5−ヘキセン、1,2−チオエポキシ−4−ビニルシクロヘキセン、2−ノルボルネンスルフィド、7−メチル−2−ノルボルネンスルフィド、7,7−ジメチル−2−ノルボルネンスルフィド、2−メチル−2−ノルボルネンスルフィド、2,3−ジメチル−2−ノルボルネンスルフィド、2,7−ジメチル−2−ノルボルネンスルフィド、2,7,7−トリメチル−2−ノルボルネンスルフィド、2,3−チオエポキシ−ビシクロ[2.2.2]オクタン、2,3−チオエポキシ−2−メチル−ビシクロ[2.2.2]オクタン、2,3−チオエポキシ−2,3−ジメチル−ビシクロ[2.2.2]オクタン、2,3−チオエポキシ−2,5−ジメチル−ビシクロ[2.2.2]オクタン、2,3−チオエポキシ−2,6−ジメチル−ビシクロ[2.2.2]オクタン、2,3−チオエポキシ−2,3,5−トリメチル−ビシクロ[2.2.2]オクタン、2,3−チオエポキシ−2,5,6−トリメチル−ビシクロ[2.2.2]オクタン、2,3−チオエポキシ−2,3,5,6−テトラメチル−ビシクロ[2.2.2]オクタン、チオエポキシヘキサヒドロフタル酸ジオクチル、チオエポキシヘキサヒドロフタル酸ジ−2−エチルヘキシル、スチベンスルフィド、フェニルチオグリシジルエーテル、3−(2,2,3,3−テトラフルオロプロポキシ)−1,2−チオエポキシプロパン、ピネンスルフィド、イソプレンモノスルフィド、1,2−チオエポキシエチルベンゼン、ナフチルチオグリシジルエーテル、3−(2−ビフェニロキシ)−1,2−チオエポキシプロパン、アリルチオグリシジルエーテル、1,1−ジフェニル−エチレンスルフィド、チオグリシジル(メタ)アクリレート、チオグリシジルブチレート、ヨードメチルチイラン、4−(2,3−チオエポキシプロピル)モルフォリン、チオグリシジルメチルエーテル、2−フェニル−プロピレンスルフィド、2,3−チオエポキシプロピル−フルフリルエーテル、2,3,4,5,6−ペンタフルオロスチレンスルフィド、エチル−3−フェニルチオグリシデート、リモネンスルフィド、チオエポキシスクシン酸、3−チオグリシドキシプロピルトリメトキシシラン、(3−チオグシリドキシプロピル)ペンタメチルジシロキサン、3−チオグリシドキシプロピル(メチル)ジメトキシシラン、3−チオグリシドキシプロピル(メチル)ジエトキシシラン、3−チオグリシドキシプロピル(メチル)ジブトキシシラン、2−(3,4−チオエポキシシクロヘキシル)エチル(メチル)ジメトキシシラン、2−(3,4−チオエポキシシクロヘキシル)エチル(フェニル)ジエトキシシラン、2,3−チオエポキシプロピル(メチル)ジメトキシシラン、2,3−チオエポキシプロピル(フェニル)ジメトキシシラン、3−チオグリシドキシプロピルトリメトキシシラン、3−チオグリシドキシプロピルトリエトキシシラン、3−チオグリシドキシプロピルトリブトキシシラン、2−(3,4−チオエポキシシクロヘキシル)エチルトリメトキシシラン、2−(3,4−チオエポキシシクロヘキシル)エチルトリエトキシシラン、2,3−チオエポキシプロピルトリメトキシシラン及び2,3−チオエポキシプロピルトリエトキシシランから選ばれ得る。
ポリフェノール化合物のチオグリシジルエーテル化物である多官能エピスルフィド化合物は、特に限定されるものではなく、具体的には、ビスフェノールA、ビスフェノールF、ビスフェノールS、4,4’−ビフェノール、テトラメチルビスフェノールA、ジメチルビスフェノールA、テトラメチルビスフェノールF、ジメチルビスフェノールF、テトラメチルビスフェノールS、ジメチルビスフェノールS、テトラメチル−4,4’−ビフェノール、ジメチル−4,4’−ビフェニルフェノール、1−(4−ヒドロキシフェニル)−2−[4−(1,1−ビス−(4−ヒドロキシフェニル)エチル)フェニル]プロパン、2,2’−メチレン−ビス(4−メチル−6−t−ブチルフェノール)、4,4’−ブチリデン−ビス(3−メチル−6−t−ブチルフェノール)、トリスヒドロキシフェニルメタン、レゾルシノール、ハイドロキノン、2,6−ジ(t−ブチル)ハイドロキノン、ピロガロール、ジイソプロピリデン骨格を有するフェノール類、1,1−ジ(4−ヒドロキシフェニル)フルオレン等のフルオレン骨格を有するフェノール類、及びフェノール化ポリブタジエン等のポリフェノール化合物のチオグリシジルエーテル化物から選ばれ得る。
脂環式エピスルフィド化合物は、脂環式エピスルフィド構造を有するエピスルフィド化合物であれば、特に限定されるものではなく、例えば、シクロヘキセンスルフィド基、トリシクロデセンスルフィド基又はシクロペンテンスルフィド基等を有するエピスルフィド化合物から選ばれ得る。
ノボラック化合物のチオグリシジルエーテル化物である多官能エピスルフィド化合物は、特に限定されるものではなく、例えば、フェノール、クレゾール類、エチルフェノール類、ブチルフェノール類、オクチルフェノール類、ビスフェノールA、ビスフェノールF、ビスフェノールS、及びナフトール類等の各種フェノールを原料とするノボラック化合物、キシリレン骨格含有フェノールノボラック化合物、ジシクロペンタジエン骨格含有フェノールノボラック化合物、ビフェニル骨格含有フェノールノボラック化合物、並びに、フルオレン骨格含有フェノールノボラック化合物等の各種ノボラック化合物のチオグリシジルエーテル化物から選ばれ得る。
芳香族エピスルフィド化合物の核水素化物は、特に限定されるものではなく、例えば、フェノール化合物(ビスフェノールA、ビスフェノールF、ビスフェノールS、4,4’−ビフェノール等)のチオグリシジルエーテル化物、又は各種フェノール(フェノール、クレゾール類、エチルフェノール類、ブチルフェノール類、オクチルフェノール類、ビスフェノールA、ビスフェノールF、ビスフェノールS、ナフトール類等)の芳香環を核水素化したもの、並びに、ノボラック化合物のチオグリシジルエーテル化物の核水素化物から選ばれ得る。
複素環式エピスルフィド化合物は、特に限定されるものではなく、例えば、イソシアヌル環、及びヒダントイン環等の複素環を有する複素環式エピスルフィド化合物から選ばれ得る。
チオグリシジルエステル系エピスルフィド化合物は、特に限定されるものではなく、例えば、ヘキサヒドロフタル酸ジグリシジルエステル及びテトラヒドロフタル酸ジグリシジルエステル等の、カルボン酸化合物から誘導されるエピスルフィド化合物から選ばれ得る。
チオグリシジルアミン系エピスルフィド化合物は、特に限定されるものではなく、例えば、アニリン、トルイジン、p−フェニレンジアミン、m−フェニレンジアミン、ジアミノジフェニルメタン誘導体及びジアミノメチルベンゼン誘導体等のアミンをチオグリシジル化したエピスルフィド化合物から選ばれ得る。
ハロゲン化フェノール類をチオグリシジル化したエピスルフィド化合物は、特に限定されるものではなく、例えば、ブロム化ビスフェノールA、ブロム化ビスフェノールF、ブロム化ビスフェノールS、ブロム化フェノールノボラック、ブロム化クレゾールノボラック、クロル化ビスフェノールS、及びクロル化ビスフェノールA等のハロゲン化フェノール類をチオグリシジルエーテル化したエピスルフィド化合物から選ばれ得る。
(含硫)多官能脂肪族エピスルフィド化合物としては、特に限定されるものではなく、具体的には、1,1−ビス(エピチオエチル)メタン、1−(エピチオエチル)−1−(β−エピチオプロピル)メタン、1,1−ビス(β−エピチオプロピル)メタン、1−(エピチオエチル)−1−(β−エピチオプロピル)エタン、1,2−ビス(β−エピチオプロピルエタン、1−(エピチオエチル)−3−(β−エピチオプロピル)ブタン、1,3−ビス(β−エピチオプロピル)プロパン、1−(エピチオエチル)−4−(β−エピチオプロピル)ペンタン、1,4−ビス(β−エピチオプロピル)ブタン、1−(エピチオエチル)−5−(β−エピチオプロピル)ヘキサン、1−(エピチオエチル)−2−(γ−エピチオブチルチオ)エタン、1−(エピチオエチル)−2−[2−(γ−エピチオブチルチオ)エチルチオ]エタン、テトラキス(β−エピチオプロピル)メタン、1,1,1−トリス(β−エピチオプロピル)プロパン、1,3−ビス(β−エピチオプロピル)−1−(β−エピチオプロピル)−2−チアプロパン、1,5−ビス(β−エピチオプロピル)−2,4−ビス(β−エピチオプロピル)−3−チアペンタン、1,3または1,4−ビス(エピチオエチル)シクロヘキサン、1,3または1,4−ビス(β−エピチオプロピル)シクロヘキサン、2,5−ビス(エピチオエチル)−1,4−ジチアン、2,5−ビス(β−エピチオプロピル)−1,4−ジチアン、4−エピチオエチル−1、2−シクロヘキセンスルフィド、2,2−ビス[4−(エピチオエチル)シクロヘキシル]プロパン、2,2−ビス[4−(β−エピチオプロピル)シクロヘキシル]プロパン、ビス[4−(エピチオエチル)シクロヘキシル]メタン、ビス[4−(β−エピチオプロピル)シクロヘキシル]メタン、ビス[4−(β−エピチオプロピル)シクロヘキシル]スルフィド、ビス[4−(エピチオエチル)シクロヘキシル]スルフィド、ビス(β−エピチオプロピル)エーテル、ビス(β−エピチオプロピルオキシ)メタン、1,2−ビス(β−エピチオプロピルオキシ)エタン、1,3−ビス(β−エピチオプロピルオキシ)プロパン、1,2−ビス(β−エピチオプロピルオキシ)プロパン、1−(β−エピチオプロピルオキシ)−2−(β−エピチオプロピルオキシメチル)プロパン、1,4−ビス(β−エピチオプロピルオキシ)ブタン、1,3−ビス(β−エピチオプロピルオキシ)ブタン、1−(β−エピチオプロピルオキシ)−3−(β−エピチオプロピルオキシメチル)ブタン、1,5−ビス(β−エピチオプロピルオキシ)ペンタン、1−(β−エピチオプロピルオキシ)−4−(β−エピチオプロピルオキシメチル)ペンタン、1,6−ビス(β−エピチオプロピルオキシ)ヘキサン、1−(β−エピチオプロピルオキシ)−5−(β−エピチオプロピルオキシメチル)ヘキサン、1−(β−エピチオプロピルオキシ)−2−[(2−β−エピチオプロピルオキシエチル)オキシ]エタン、1−(β−エピチオプロピルオキシ)−2−[{2−(2−β−エピチオプロピルオキシエチル)オキシエチル}オキシ]エタン、テトラキス(β−エピチオプロピルオキシメチル)メタン、1,1,1−トリス(β−エピチオプロピルオキシメチル)プロパン、1,5−ビス(β−エピチオプロピルオキシ)−2−(β−エピチオプロピルオキシメチル)−3−チアペンタン、1,5−ビス(β−エピチオプロピルオキシ)−2,4−ビス(β−エピチオプロピルオキシメチル)−3−チアペンタン;
分子内にエピスルフィド基を有するシリコーン化合物は、特に限定されるものではなく、例えば、下記式(7)で表される化合物から選ばれ得る。
(R70R71R72SiO1/2)a(R73R74SiO2/2)b(R75SiO3/2)c(SiO4/2)d (7)
異種重合性官能基含有エピスルフィド化合物は、特に限定されるものではなく、例えば下記式(8)で表される化合物から選ばれ得る。
指標α=αc/αb (2)
αc:前記カーボネート化合物のカーボネート基の物質量(mol)
αb:(B)三ハロゲン化ホウ素の物質量(mol)
指標β=αb/αt×100 (9)
αb:(B)三ハロゲン化ホウ素の物質量(mol)
αt:(C)エピスルフィド化合物に含まれるエピスルフィド基の物質量(mol)
(B)三ハロゲン化ホウ素の物質量(mol)と、(C)エピスルフィド化合物に含まれるエピスルフィド基の物質量(mol)との比が1:20であるとき、指標β=5となる。
(B)三ハロゲン化ホウ素の物質量(mol)と、(C)エピスルフィド化合物に含まれるエピスルフィド基の物質量(mol)との比が1:50であるとき、指標β=2となる。
(B)三ハロゲン化ホウ素の物質量(mol)と、(C)エピスルフィド化合物に含まれるエピスルフィド基の物質量(mol)との比が1:100であるとき、指標β=1となる。
(B)三ハロゲン化ホウ素の物質量(mol)と、(C)エピスルフィド化合物に含まれるエピスルフィド基の物質量(mol)との比が1:200であるとき、指標β=0.5となる。
(B)三ハロゲン化ホウ素の物質量(mol)と、(C)エピスルフィド化合物に含まれるエピスルフィド基の物質量(mol)との比が1:100000であるとき、指標β=0.001となる。
(B)三ハロゲン化ホウ素の物質量(mol)と、(C)エピスルフィド化合物に含まれるエピスルフィド基の物質量(mol)との比が1:20000であるとき、指標β=0.005となる。
(B)三ハロゲン化ホウ素の物質量(mol)と、(C)エピスルフィド化合物に含まれるエピスルフィド基の物質量(mol)との比が1:10000であるとき、指標β=0.01となる。
環状エステル化合物は、環状構造内にエステル基を有する化合物であれば特に限定されるものではなく、具体的には、エタノ−2−ラクトン、プロパノ−2−ラクトン、プロパノ−3−ラクトン、ブタノ−2−ラクトン、ブタノ−3−ラクトン、ブタノ−4−ラクトン、3−メチル−ブタノ−4−ラクトン、ペンタノ−2−ラクトン、ペンタノ−3−ラクトン、ペンタノ−4−ラクトン、ペンタノ−5−ラクトン、4−メチル−ペンタノ−4−ラクトン、ヘキサノ−2−ラクトン、ヘキサノ−3−ラクトン、ヘキサノ−4−ラクトン、ヘキサノ−5−ラクトン、ヘキサノ−6−ラクトン、ヘプタノ−2−ラクトン、ヘプタノ−3−ラクトン、ヘプタノ−4−ラクトン、ヘプタノ−5−ラクトン、ヘプタノ−6−ラクトン、ヘプタノ−7−ラクトン、オクタノ−2−ラクトン、オクタノ−3−ラクトン、オクタノ−4−ラクトン、オクタノ−5−ラクトン、オクタノ−6−ラクトン、オクタノ−7−ラクトン、オクタノ−8−ラクトン、ノナノ−2−ラクトン、ノナノ−3−ラクトン、ノナノ−4−ラクトン、ノナノ−5−ラクトン、ノナノ−6−ラクトン、ノナノ−7−ラクトン、ノナノ−8−ラクトン、ノナノ−9−ラクトン、デカノ−2−ラクトン、デカノ−3−ラクトン、デカノ−4−ラクトン、デカノ−5−ラクトン、デカノ−6−ラクトン、デカノ−7−ラクトン、デカノ−8−ラクトン、デカノ−9−ラクトン、デカノ−10−ラクトン;
環状シロキサン化合物は、環状構造がシロキサン結合により形成されている化合物であれば特に限定されるものではなく、具体的には、以下の群から選ばれ得る少なくとも1種の化合物である。
水酸基含有化合物は、構造内に水酸基を有する化合物であれば特に限定されるものではなく、具体的には、以下の群から選ばれ得る少なくとも1種の化合物である。
指標γ=αd/αt×100 (10)
αd:(D)連鎖移動剤の物質量(mol)
αt:(C)エピスルフィド化合物に含まれるエピスルフィド基の物質量(mol)
(D)連鎖移動剤の物質量(mol)と、(C)エピスルフィド化合物に含まれるエピスルフィド基の物質量(mol)との比が、1:20であるとき、指標γ=5となる。
(D)連鎖移動剤の物質量(mol)と、(C)エピスルフィド化合物に含まれるエピスルフィド基の物質量(mol)との比が、1:50であるとき、指標γ=2となる。
(D)連鎖移動剤の物質量(mol)と、(C)エピスルフィド化合物に含まれるエピスルフィド基の物質量(mol)との比が、1:10000であるとき、指標γ=0.01となる。
(D)連鎖移動剤の物質量(mol)と、(C)エピスルフィド化合物に含まれるエピスルフィド基の物質量(mol)との比が、1:2000であるとき、指標γ=0.05となる。
(D)連鎖移動剤の物質量(mol)と、(C)エピスルフィド化合物に含まれるエピスルフィド基の物質量(mol)との比が、1:1000であるとき、指標γ=0.1となる。
11B−NMR測定は、以下の手順で行った。
(1)サンプル瓶に、10mgのトリメトキシボラン(和光純薬工業株式会社製)を計りとり、クロロホルム−d(和光純薬工業株式会社製)を加え、全体量を1gに調整した。
(2)サンプル瓶に、三ハロゲン化ホウ素−カーボネート化合物を調製する際に用いた、三ハロゲン化ホウ素化合物10mgを計りとり、クロロホルム−d(和光純薬工業株式会社製)を加え、全体量を1gに調整した。
(3)サンプル瓶に、調製した三ハロゲン化ホウ素−カーボネート化合物10mgを計りとり、クロロホルム−d(和光純薬工業株式会社製)を加え、全体量を1gに調整した。
(4)上記(2)の溶液を、直径5mmφのNMRチューブ内に挿入可能な特殊NMRチューブ(例えば、日本精密化学株式会社製「N−502B」等)に移した。
(5)上記(1)の溶液を直径5mmφのNMRチューブに移し、上記(4)の特殊NMRチューブを挿入し、下記条件で、11B−NMRを測定した。
フーリエ変換核磁気共鳴装置:日本電子株式会社製「α−400型」
核種:11B
積算回数:1000回
(6)上記(3)の溶液を、直径5mmφのNMRチューブ内に挿入可能な特殊NMRチューブ(例えば、日本精密化学株式会社製「N−502B」等)に移した。
(7)上記(1)の溶液を直径5mmφのNMRチューブに移し、上記(6)の特殊NMRチューブを挿入し、上記(5)と同様の方法で、11B−NMRを測定した。
(8)上記(5)及び(7)で得られた測定結果において、トリメトキシボランのピークを18ppmとし、(7)で得られたピークに、(5)で得られたピークと異なるピークが検出された場合、調製した三ハロゲン化ホウ素−カーボネート化合物では錯体が形成されていると判断した。
1H−NMR測定は、以下の手順で行った。
(1)サンプル瓶に、10mgのサンプルと、20mgの内部標準物質を計りとり、更にクロロホルム−d(和光純薬工業株式会社製)を加え、全体量を1gに調整した。
・内部標準物質:1,1,2,2−テトラブロモエタン(東京化成工業株式会社製、以下「TBE」、という)
(2)上記(1)の溶液を、直径5mmφのNMRチューブに移し、下記条件で、1H−NMRを測定した。
フーリエ変換核磁気共鳴装置:日本電子株式会社製「α−400型」
核種:1H
積算回数:200回
上記測定結果から、以下の手順で、エピスルフィド当量を算出した。
(3)1H−NMRチャートから、エピスルフィド基由来ピークの面積値を算出した。
ここで、エピスルフィド基由来のピークとは、エピスルフィド基を構成する炭化水素上の1つの水素に由来するピークを指す。エピスルフィド化合物を構成するエピスルフィド基に由来する水素以外の水素に由来するピークと重複しないピークが適宜選択される。
(4)1H−NMRチャートから、内部標準物質由来ピークの面積値を算出した。
(5)上記(3)及び(4)で算出した面積値を、下記式に代入し、エピスルフィド当量(g/mol)を求めた。
エピスルフィド当量(g/mol)=(SAMG/EPIA)×(TBEM/TBEG)×(TBEA/2)
EPIA:エピスルフィド基由来ピークの面積値
TBEA:TBEの2つの水素に由来するピークの面積値
TBEG:1H−NMR測定を行う溶液を調製する際に、使用したTBEの重量(g)(本実施例においては20mg)
TBEM:TBEの分子量
SAMG:1H−NMR測定を行う溶液を調製する際に、使用したサンプルの重量(g)(本実施例においては10mg)
サンプルに含有されるエピスルフィド化合物中のエピスルフィド基を構成する炭化水素上の水素が1H−NMRの測定上同一のピークとして観測される場合には、(5)の手順を以下のように変更することで算出が可能となる。
(5−2)上記(3)及び(4)で算出した面積値を、下記式に代入し、エピスルフィド当量(g/mol)を求めた。
エピスルフィド当量(g/mol)=SAMG×(エピスルフィド基由来ピークを構成している水素の個数/EPIA)×(TBEM/TBEG)×(TBEA/2)
混合指標αは、以下の式(2)により算出した。
指標α=αc/αb (2)
ここで、
αc:前記カーボネート化合物のカーボネート基の物質量(mol)
αb:(B)三ハロゲン化ホウ素の物質量(mol)、をそれぞれ示す。
混合指標βは、以下の式(9)により算出した。
指標β=αb/αt×100 (9)
ここで、
αb:(B)三ハロゲン化ホウ素の物質量(mol)
αt:(C)エピスルフィド化合物に含まれるエピスルフィド基の物質量(mol)、をそれぞれ示す。
1H−NMR測定は、以下の手順で行った。
(1)サンプル瓶に、10mgのサンプルと、20mgの内部標準物質を計りとり、更にクロロホルム−d(和光純薬工業株式会社製)を加え、全体量を1gに調整した。
・内部標準物質:1,1,2,2−テトラブロモエタン(東京化成工業株式会社製、以下「TBE」、という)
(2)上記(1)の溶液を、直径5mmφのNMRチューブに移し、下記条件で、1H−NMRを測定した。
フーリエ変換核磁気共鳴装置:日本電子株式会社製「α−400型」
核種:1H
積算回数:200回
上記測定結果から、以下の手順で、エピスルフィド基反応率を算出した。
(3)1H−NMRチャートから、エピスルフィド基由来ピークの面積値を算出した。
ここで、エピスルフィド基由来のピークとは、エピスルフィド基を構成する炭化水素上の1つの水素に由来するピークを指す。エピスルフィド化合物を構成するエピスルフィド基に由来する水素以外の水素に由来するピークと重複しないピークが適宜選択される。
(4)1H−NMRチャートから、内部標準物質由来ピークの面積値を算出した。
(5)上記(3)及び(4)で算出した面積値を、下記式に代入し、エピスルフィド基反応率(%)を求めた。
エピスルフィド基反応率(%)=100−EPIA×(TBEG/TBEM)×(2/TBEA)×(REAG/SAMG)×(WPT/EPIG)×100
EPIA:エピスルフィド基由来ピークの面積値
TBEA:TBEの2つの水素に由来するピークの面積値
EPIG:組成物を調製する際に使用したエピスルフィド化合物の重量(g)
WPT:組成物を調製する際に使用したエピスルフィド化合物のエピスルフィド当量(g/mol)
REAG:組成物の重量(g)
TBEG:1H−NMR測定を行う溶液を調製する際に、使用したTBEの重量(g)(本実施例においては20mg)
TBEM:TBEの分子量
SAMG:1H−NMR測定を行う溶液を調製する際に、使用したサンプルの重量(g)(本実施例においては10mg)
サンプルに含有されるエピスルフィド化合物中のエピスルフィド基を構成する炭化水素上の水素が1H−NMRの測定上同一のピークとして観測される場合には、(5)の手順を以下のように変更することで算出が可能となる。
(5−2)上記(3)及び(4)で算出した面積値を、下記式に代入し、エピスルフィド基反応率(%)を求めた。
エピスルフィド基反応率(%)=100−{EPIA/(エピスルフィド基由来ピークを構成している水素の個数)}×(TBEG/TBEM)×(2/TBEA)×(REAG/SAMG)×(WPT/EPIG)×100
EA法において、サンプルがクロロホルム−dに溶解しない場合には、EB法によりエピスルフィド基反応率が算出される。
FT−IR測定は、以下の手順で行った。
(1)メノウ製の乳鉢に、2mgのサンプルと、100mgの臭化カリウム(Aldrich社製、IRグレード)を計りとり、メノウ製の乳棒にて均一になるまで粉砕した。
(2)上記(1)の試料50mgを錠剤成型器にて、円盤状に成型した。
(3)上記(2)の成型体を錠剤サンプルホルダーに設置し、下記条件で、FT−IR測定を行った。
フーリエ変換赤外分光装置:サーモフィッシャーサイエンティフィック社製「Nicolet6700型」
分解能:4cm−1
測定法:透過法
積算回数:128回
上記測定結果から、以下の手順でエピスルフィド基反応率を算出した。
(4)FT−IRチャートから、エピスルフィド基由来ピークの面積値を算出した。
ここで、エピスルフィド基由来のピークとは、エピスルフィド基を構成する原子間の振動に由来するピークを指す。サンプルに含有される化合物において、エピスルフィド基に由来するピーク以外の原子間の振動に由来するピークと重複しないピークが適宜選択される。
(5)(4)で算出した面積値を、下記式に代入し、エピスルフィド基反応率(%)を求めた。
エピスルフィド基反応率(%)=100−RIRA/SIRA×100
RIRA:サンプルを測定した結果得られたFT−IRチャートにおいて、エピスルフィド基由来のピーク面積
SIRA:サンプルを作製する際に用いた、重合前のエピスルフィド化合物を測定した結果得られたFT−IRチャートにおける、エピスルフィド基由来のピーク面積。
1H−NMR測定は、以下の手順で行った。
(1)サンプル瓶に、10mgのサンプルと、20mgの内部標準物質を計りとり、更にクロロホルム−d(和光純薬工業株式会社製)を加え、全体量を1gに調整した。
・内部標準物質:1,1,2,2−テトラブロモエタン(東京化成工業株式会社製、以下「TBE」、という)
(2)上記(1)の溶液を、直径5mmφのNMRチューブに移し、下記条件で、1H−NMRを測定した。
フーリエ変換核磁気共鳴装置:日本電子株式会社製「α−400型」
核種:1H
積算回数:200回
上記測定結果から、以下の手順で、ビニル基生成率を算出した。
(3)1H−NMRチャートから、ビニル基由来ピークの面積値を算出した。
ここで、ビニル基由来のピークとは、ビニル基を構成する炭化水素上の1つの水素に由来するピークを指す。サンプルに含有される化合物を構成する水素であって、ビニル基に由来する水素以外の水素に由来するピークと重複しないピークが適宜選択される。
(4)1H−NMRチャートから、内部標準物質由来ピークの面積値を算出した。
(5)上記(3)及び(4)で算出した面積値を、下記式に代入し、エピスルフィド当量(g/mol)を求めた。
ビニル基生成率(%)=VINA×(TBEG/TBEM)×(2/TBEA)×(REAG/SAMG)×(WPT/EPIG)×100
VINA:ビニル基由来ピークの面積値
TBEA:TEBの2つの水素に由来するピークの面積値
EPIG:組成物を調製する際に使用したエピスルフィド化合物の重量(g)
WPT:組成物を調製する際に使用したエピスルフィド化合物のエピスルフィド当量(g/mol)
REAG:組成物の重量(g)
TBEG:1H−NMR測定を行う溶液を調製する際に、使用したTBEの重量(g)(本実施例においては20mg)
TBEM:TBEの分子量
SAMG:1H−NMR測定を行う溶液を調製する際に、使用したサンプルの重量(g)(本実施例においては10mg)
ビニル基を構成する炭化水素上の水素が1H−NMRの測定上同一のピークとして観測される場合には、(5)の手順を以下のように変更することで算出が可能となる。
(5−2)上記(3)及び(4)で算出した面積値を、下記式に代入し、ビニル基生成率(%)を求めた。
ビニル基生成率(%)={VINA/(ビニル基由来ピークを構成している水素の個数)}×(TBEG/TBEM)×(2/TBEA)×(REAG/SAMG)×(WPT/EPIG)×100
調製した組成物の一部を、20℃に設定された恒温器に入れ、1時間保持した後、EA法にてエピスルフィド基反応率を算出した。
安定性は、エピスルフィド基反応率が10%以下の場合に良好(「A」)と判断し、5%以下の場合に特に良好(「AA」)と判断し、これら以外の場合に不良(「C」)と判断した。
安定性評価Aにおいて、組成物がクロロホルム−dに完全に溶解しない場合には、EB法にてエピスルフィド基反応率を算出した。
安定性は、エピスルフィド基反応率が10%以下の場合に良好(「A」)と判断し、5%以下の場合に特に良好(「AA」)と判断し、これら以外の場合に不良(「C」)と判断した。
EA法にて、得られた重合物のエピスルフィド基反応率を算出した。
重合性は、エピスルフィド基反応率が90%以上の場合に良好(「A」)と判断し、95%以上の場合に特に良好(「AA」)と判断し、これら以外の場合に不良(「C」)と判断した。
重合性評価Aにおいて、重合物がクロロホルム−dに完全に溶解しない場合には、EB法にてエピスルフィド基反応率を算出した。
重合性は、エピスルフィド基反応率が90%以上の場合に良好(「A」)と判断し、95%以上の場合に特に良好(「AA」)と判断し、これら以外の場合に不良(「C」)と判断した。
調製した重合物のビニル基生成率を算出した。
副反応性は、ビニル基生成率が5%以下の場合に良好(「A」)と判断し、2%以下の場合に特に良好(「AA」)と判断し、これら以外の場合に不良(「C」)と判断した。
副反応性評価Aにおいて、重合物がクロロホルム−dに完全に溶解しない場合には、以下の方法にて評価を実施した。
(1)評価用サンプルを凍結粉砕機にて、紛体状サンプルとした。
(2)上記(1)の紛体状サンプルを、直径4mmφのNMRチューブに移し、下記条件で、固体13C−NMRを測定した。
フーリエ変換核磁気共鳴装置:日本電子株式会社製「ECA700型」
核種:13C
積算回数:16,000回
測定方法:CP/MAS法
MAS:10,000Hz
(3)上記測定結果より、ビニル基由来ピークが観測されなかった場合に特に良好(「AA」)と判断し、観測された場合に不良(「C」)と判断した。
安定性評価、重合性評価、副反応性評価の全ての評価において、特に良好であると判断された場合、及び少なくとも1つの評価において良好と判断され、それ以外の評価において特に良好又は良好と判断された場合に、総合判定として合格((「AA」又は「A」)とした。それ以外の場合については、全て不合格(「C」)とした。
(エポキシ化合物)
(1)エポキシ化合物B:エチレンオキシド(Aldrich社製、以下、「EO」という。)
・エポキシ当量(WPE):44g/eq.
(2)エポキシ化合物C:プロピレンオキシド(和光純薬工業株式会社製、以下、「PO」という。)
・エポキシ当量(WPE):58g/eq.
(3)エポキシ化合物D:1,2−エポキシブタン(東京化成工業株式会社製、以下、「12EB」という。)
・エポキシ当量(WPE):72g/eq.
(4)エポキシ化合物E:1,2−エポキシペンタン(東京化成工業株式会社製、以下、「12EP」という。)
・エポキシ当量(WPE):86g/eq.
(5)エポキシ化合物F:1,2−エポキシヘキサン(東京化成工業株式会社製、以下、「12EH」という。)
・エポキシ当量(WPE):100g/eq.
(6)エポキシ化合物G:1,2−エポキシヘプタン(東京化成工業株式会社製、以下、「12EHP」という。)
・エポキシ当量(WPE):114g/eq.
(7)エポキシ化合物H:1,2−エポキシオクタン(和光純薬工業株式会社製、以下、「12EO」という。)
・エポキシ当量(WPE):128g/eq.
(8)エポキシ化合物I:1,2−エポキシデカン(和光純薬工業株式会社製、以下、「12ED」という。)
・エポキシ当量(WPE):156g/eq.
(9)エポキシ化合物J:1,2−エポキシドデカン(和光純薬工業株式会社製、以下、「12EDD」という。)
・エポキシ当量(WPE):184g/eq.
(10)エポキシ化合物K:1,2−エポキシテトラデカン(和光純薬工業株式会社製、以下、「12ETD」という。)
・エポキシ当量(WPE):212g/eq.
(11)エポキシ化合物L:1,2−エポキシヘキサデカン(東京化成工業株式会社製、以下、「12EHD」という。)
・エポキシ当量(WPE):240g/eq.
(12)エポキシ化合物M:1,2−エポキシオクタデカン(東京化成工業株式会社製、以下、「12EOD」という。)
・エポキシ当量(WPE):268g/eq.
(13)エポキシ化合物N:1,2−エポキシエイコサン(東京化成工業株式会社製、以下、「12EEC」という。)
・エポキシ当量(WPE):297g/eq.
(14)エポキシ化合物A:フェニルグリシジルエーテル(和光純薬工業株式会社製、以下、「PGE」という。)
・エポキシ当量(WPE):150g/eq.
(15)エポキシ化合物O:ビスフェノールA型エポキシ化合物(以下、「Bis−A−1」という。)
・商品名:旭化成エポキシ株式会社製、「AER」
・エポキシ当量(WPE):189g/eq.
(16)エポキシ化合物P:水添ビスフェノールA型エポキシ化合物(以下、「水添Bis−A」という。)
・商品名:ジャパンエポキシレジン社製、「YX8000」
・エポキシ当量(WPE):205g/eq.
(17)エポキシ化合物Q:ビスフェノールA型エポキシ化合物(以下、「Bis−A−2」という。)
・商品名:旭化成エポキシ株式会社製、「AER」
・エポキシ当量(WPE):480g/eq.
(18)エポキシ化合物R:ビスフェノールA型エポキシ化合物(以下、「Bis−A−3」という。)
・商品名:旭化成エポキシ株式会社製、「AER」
・エポキシ当量(WPE):560g/eq.
(19)エポキシ化合物S:ビスフェノールA型エポキシ化合物(以下、「Bis−A−4」という。)
・商品名:旭化成エポキシ株式会社製、「AER」
・エポキシ当量(WPE):650g/eq.
(20)エポキシ化合物T:シクロペンテンオキシド(Aldrich社製、以下、「C5O」という。)
・エポキシ当量(WPE):84g/eq.
(21)エポキシ化合物U:シクロヘキセンオキシド(Aldrich社製、以下、「C6O」という。)
・エポキシ当量(WPE):98g/eq.
(22)エポキシ化合物V:シクロヘプテンオキシド(Aldrich社製、以下、「C7O」という。)
・エポキシ当量(WPE):112g/eq.
(23)エポキシ化合物W:シクロオクテンオキシド(Aldrich社製、以下、「C8O」という。)
・エポキシ当量(WPE):126g/eq.
(24)エポキシ化合物X:脂環式エポキシ化合物(以下、「CEL」という。)
・商品名:ダイセル化学工業株式会社、「セロキサイド2021P」
・エポキシ当量(WPE):131g/eq.
(25)エポキシ化合物Y:ビス(2,3−エポキシプロピル)ジスルフィド(以下、「BEDS」という。)
特開2002−194083に記載の方法に従ってBEDSを合成した。
・エポキシ当量(WPE):91g/eq.
(26)エポキシ化合物Z:1,3−ビス(3−グリシドキシプロピル)−1,1,3,3−テトラメチルジシロキサン(以下、「BGTD」という。)
・商品名:信越化学工業株式会社、「LS−7970」
・エポキシ当量(WPE):182g/eq.
(27)エポキシ化合物AA:ビス[2−(3,4−エポキシシクロヘキシル)エチル]テトラメチルジシロキサン(以下、「BCTD」という。)
・商品名:Gelest, Inc.、「SIB1092.0」
・エポキシ当量(WPE):192g/eq.
(28)エポキシ化合物AB:1,3,5,7−テトラ−(3−グリシドキシプロピル)テトラメチルシクロテトラシロキサン(以下、「TGCS」という。)
Euro.Polym.J.2010,46,1545.記載の方法に従って、TGCSを合成した。
・エポキシ当量(WPE):174g/eq.
(29)エポキシ化合物AC:1,3,5,7−テトラ−[2−(3,4−エポキシシクロヘキシルエチル)]テトラメチルシクロテトラシロキサン(以下、「TCCS」という。)
特開2000−103859に記載の方法に従って、TCCSを合成した。
・エポキシ当量(WPE):184g/eq.
(30)エポキシ化合物AD:ブタジエンモノオキシド(和光純薬工業株式会社製、以下、「BDMO」という。)
・エポキシ当量(WPE):70g/eq.
(31)エポキシ化合物AE:1,2−エポキシ−5−ヘキセン(和光純薬株式会社製、以下、「EPHE」という。)
・エポキシ当量(WPE):98g/eq.
(32)エポキシ化合物AF:アリルグリシジルエーテル(和光純薬株式会社製、以下、「AGE」という。)
・エポキシ当量(WPE):114g/eq.
(33)エポキシ化合物AG:1,2−エポキシ−4−ビニルシクロヘキサン(Aldrich社製、以下、「EVCH」という。)
・エポキシ当量(WPE):124g/eq.
(34)エポキシ化合物AH:グリシジルメタクリレート(和光純薬株式会社製、以下、「GLMT」という。)
・エポキシ当量:142g/eq.
(35)チア化剤:チオ尿素(和光純薬工業株式会社製、以下、「TU」という。)
(36)水酸基化合物A:1,2−プロピレングリコール(和光純薬工業株式会社製、以下、「12PG」という。)
(37)水酸基化合物B:1,3−プロピレングリコール(和光純薬工業株式会社製、以下、「13PG」という。)
(38)水酸基化合物C:1,2−ブタンジオール(和光純薬工業株式会社製、以下、「12BD」という。)
(39)水酸基化合物D:1,3−ブタンジオール(和光純薬工業株式会社製、以下、「13BD」という。)
(40)カーボネート化合物A:ジメチルカーボネート(東京化成工業株式会社製、以下、「MCBA」という。)
(41)カーボネート化合物B:1,3−ジオキソラン−2−オン(東京化成工業株式会社製、以下、「MCBB」という。別名として、エチレンカーボネート、とも表現される。)
(42)カーボネート化合物C:エチルメチルカーボネート(東京化成工業株式会社製、以下、「MCBC」という。)
(43)カーボネート化合物D:4−メチル−1,3−ジオキソラン−2−オン(東京化成工業株式会社製、以下、「MCBD」という。別名として、プロピレンカーボネート、とも表現される。)
(44)カーボネート化合物E:1,3−ジオキサン−2−オン(東京化成工業株式会社製、以下、「MCBE」という。)
(45)カーボネート化合物F:ジエチルカーボネート(東京化成工業株式会社製、以下、「MCBF」という。)
(46)カーボネート化合物G:4−エチル−1,3−ジオキソラン−2−オン(東京化成工業株式会社製、以下、「MCBG」という。別名として、1,2−ブチレンカーボネート、とも表現される。)
(47)カーボネート化合物H:4−(メトキシメチル)−1,3−ジオキソラン−2−オン(東京化成工業株式会社製、以下、「MCBH」という。)
(48)カーボネート化合物I:ジプロピルカーボネート(Aldrich社製、以下、「MCBI」という。)
(48)カーボネート化合物J:5,5−ジメチル−1,3−ジオキサン−2−オン(和光純薬工業株式会社製、以下、「MCBJ」という。)
(49)カーボネート化合物K:5,5−ジエチル−1,3−ジオキサン−2−オン(Aldrich社製、以下、「MCBK」という。)
(50)カーボネート化合物L:3,5−ジメチルフェニルエチルカーボネート(Aldrich社製、以下、「MCBL」という。)
(51)カーボネート化合物M:ジフェニルカーボネート(東京化成工業株式会社製、以下、「MCBM」という。)
(52)カーボネート化合物N:ベンジルフェニルカーボネート(東京化成工業株式会社製、以下、「MCBN」という。)
(53)カーボネート化合物O:ジベンジルカーボネート(東京化成工業株式会社製、以下、「MCBO」という。)
(54)カーボネート化合物P:ビス(2−メトキシフェニル)カーボネート(東京化成工業株式会社製、以下、「MCBP」という。)
(55)カーボネート化合物Q:メチル2−({[2−(メトキシカルボニル)フェノキシ]カルボニル}オキシ)ベンゾアート(Aldrich社製、以下、「MCBQ」という。)
(56)カーボネート化合物R:ジドデシルカーボネート(Aldrich社製、以下、「MCBR」という。)
(57)カーボネート化合物S:エチレングリコールビス(メチルカーボネート)(東京化成工業株式会社製、以下、「MCBS」という。)
(58)カーボネート化合物T:エリスリトールビス(カーボネート)(Aldrich社製、以下、「MCBT」という。)
(59)カーボネート化合物U:エチレングリコールビス(エチルカーボネート)(東京化成工業株式会社製、以下、「MCBU」という。)
(60)三ハロゲン化ホウ素化合物A:三フッ化ホウ素ジメチルエーテル錯体(和光純薬工業株式会社製、以下、「BF3DME」という。)
(61)三ハロゲン化ホウ素化合物B:三フッ化ホウ素ジエチルエーテル錯体(和光純薬工業株式会社製、以下、「BF3DEE」という。)
(62)三ハロゲン化ホウ素化合物C:三フッ化ホウ素ジブチルエーテル錯体(Aldrich社製、以下、「BF3DBE」という。)
(63)三ハロゲン化ホウ素化合物D:三フッ化ホウ素tert−ブチルメチルエーテル錯体(Aldrich社製、以下、「BF3TBME」という。)
(64)三ハロゲン化ホウ素化合物E:三フッ化ホウ素テトラヒドロフラン錯体(Aldrich社製、以下、「BF3THF」という。)
(65)三ハロゲン化ホウ素化合物F:三フッ化ホウ素メチルスルフィド錯体(Aldrich社製、以下、「BF3DMS」という。)
(66)三ハロゲン化ホウ素化合物G:三フッ化ホウ素メタノール錯体(東京化成工業株式会社製、以下、「BF3MNOL」という。)
(67)三ハロゲン化ホウ素化合物H:三フッ化ホウ素プロパノール錯体(Aldrich社製、以下、「BF3PNOL」という。)
(68)三ハロゲン化ホウ素化合物I:三フッ化ホウ素酢酸錯体(Aldrich社製、以下、「BF3ACOH」という。)
(69)三ハロゲン化ホウ素化合物J:三フッ化ホウ素フェノール錯体(Aldrich社製、以下、「BF3PHNOL」という。)
(70)三ハロゲン化ホウ素化合物K:三フッ化ホウ素エチルアミン錯体(Aldrich社製、以下、「BF3MEA」という。)
(71)三ハロゲン化ホウ素化合物L:三フッ化ホウ素ピペリジン錯体(東京化成工業株式会社製、以下、「BF3PPD」という。)
(72)三ハロゲン化ホウ素化合物M:三塩化ホウ素(1.0mol/Lジクロロメタン溶液)(Aldrich社製、以下、「BCl3DCM」という。)
(73)三ハロゲン化ホウ素化合物N:三臭化ホウ素(1.0mol/Lジクロロメタン溶液)(Aldrich社製、以下、「BBr3DCM」という。)
(74)ホスホニウム塩化合物:テトラ−n−ブチルホスホニウムブロミド(和光純薬工業株式会社製、以下、「TBPB」という。)
(75)アミン化合物A:トリブチルアミン(和光純薬工業株式会社製、以下、「TBA」という。)
(76)アミン化合物B:N,N−ジメチルシクロヘキシルアミン(和光純薬工業株式会社製、以下、「DMCHA」という。)
(77)アミン化合物C:N,N−ジエチルエタノールアミン(和光純薬工業株式会社製、以下、「DEENA」という。)
(78)スルホニウム塩化合物A:商品名「SI−25」(三新化学工業株式会社製、以下、「S25」という。)
(79)スルホニウム塩化合物B:商品名「SI−60」(三新化学工業株式会社製、以下、「S60」という。)
(80)スルホニウム塩化合物C:商品名「SI−100」(三新化学工業株式会社製、以下、「S100」という。)
(81)スルホニウム塩化合物D:商品名「SI−150」(三新化学工業株式会社製、以下、「S150」という。)
(82)スルホニウム塩化合物E:商品名「SI−180」(三新化学工業株式会社製、以下、「S180」という。)
(83)添加化合物A:ジクロロメタン(和光純薬工業株式会社製、以下、「DCM」という。)
(84)添加化合物B:ジエチルエーテル(和光純薬工業株式会社製、以下、「DEE」という。)
(85)連鎖移動剤A:1−ブタノール(和光純薬工業株式会社製、以下、「CTRA」という。)
(86)連鎖移動剤B:2−ブタノール(和光純薬工業株式会社製、以下、「CTRB」という。)
(87)連鎖移動剤C:エチレングリコール(和光純薬工業株式会社製、以下、「CTRC」という。)
(88)連鎖移動剤D:1,2−プロパンジオール(和光純薬工業株式会社製、以下、「CTRD」という。)
(89)連鎖移動剤E:2,3−ブタンジオール(和光純薬工業株式会社製、以下、「CTRE」という。)
(90)連鎖移動剤F:ブタノ−4−ラクトン(和光純薬工業株式会社製、以下、「CTRF」という。)
(91)連鎖移動剤G:ペンタノ−4−ラクトン(Aldrich社製、以下、「CTRG」という。)
(92)連鎖移動剤H:1,3−ジオキサン−2−オン(Aldrich社製、以下、「CTRH」という。)
(93)連鎖移動剤I:ヘキサメチルシクロトリシロキサン(信越化学社製、以下、「CTRI」という。)
(94)連鎖移動剤J:オクタメチルシクロテトラシロキサン(信越化学社製、以下、「CTRJ」という。)
<エピスルフィド化合物の製造>
以下の手順に従って、エピスルフィド化合物を製造した。
(1)準備:マグネチックスターラー上に、水及び攪拌子が入った投げ込み式冷却加熱ユニットが取り付けられたウォーターバス、又はオイル及び攪拌子が入ったオイルバスを載せ、所定の温度となるように設定した。
(2)各原料を、表1の組成比率に従って、攪拌子を投入したフラスコに入れて混合攪拌し、チア化剤が溶解した均一な反応液とした。
(3)表2の反応温度、反応時間に従って、反応を行った。
(4)反応液を、温度が室温になるまで、静置した。
(5)反応液にジエチルエーテル(和光純薬工業株式会社製)及び超純水(和光純薬工業株式会社製)を加え、混合攪拌した後、攪拌を止め、ジエチルエーテル層と超純水層が層分離するまで静置し、ジエチルエーテル層を取り出した。
(6)上記(5)で得られたジエチルエーテル層に、飽和食塩水を加え、混合攪拌した。その後、攪拌を止め、ジエチルエーテル層と、飽和食塩水層とが層分離するまで静置し、ジエチルエーテル層のみを取り出した。
(7)上記(6)で得られたジエチルエーテル層に無水硫酸マグネシウム(和光純薬株式会社製)を加え、混合攪拌し、濾過により無水硫酸マグネシウムを除去し、ジエチルエーテル層を得た。
(8)上記(7)で得られたジエチルエーテル層に含有される低沸点化合物(ジエチルエーテルを含む)を、ロータリーエバポレーターを用いて溜去し、エピスルフィド化合物を含有する反応生成物を得た。
(9)上記(8)で得られた反応生成物を、以下の(A)又は(B)の方法により、精製した。
(A)新実験科学講座(丸善株式会社)及び化学実験マニュアル(技報堂出版株式会社)に例示されている方法を参考に、蒸留することで、エピスルフィド化合物を精製した。
(B)新実験科学講座(丸善株式会社)及び化学実験マニュアル(技報堂出版株式会社)に例示されている方法を参考に、カラムクロマトグラフィーにより分離し、用いた展開溶媒を溜去することで、エピスルフィド化合物を精製した。
なお、カラムクロマトグラフィーの条件としては、充填剤としてシリカゲル60N(球状、中性)(関東化学株式会社製)を用い、展開溶媒としてn−ヘキサンから徐々に酢酸エチルの含有量を増やした混合溶媒を用いた。
本製造例では、(A)の方法により精製した。
(10)上記(9)で得られたエピスルフィド化合物のWPTを算出した。
表1の組成比率、及び表2の反応温度、反応時間、精製方法とした以外は、製造例1と同様の方法により、エピスルフィド化合物を製造した。
<三ハロゲン化ホウ素−カーボネート化合物の準備>
(1)準備:マグネチックスターラー上に、投げ込み式冷却加熱ユニットが取り付けられたウォーターバスを載せ、そこに水及び攪拌子を入れた。投げ込み式冷却加熱ユニットを起動させ、水の温度が20℃となるように設定した。
(2)窒素雰囲気とした反応容器を上記(1)のウォーターバスに設置し、表3の組成比率に従って各原料を反応容器に添加し、1時間撹拌した。
(3)反応容器に減圧溜去装置を取り付け、徐々に減圧を行い、最終的に2kPaまで減圧し、4時間維持した。
(4)上記(3)で得られた反応液を用い、11B−NMRによる解析を行うことで、錯体が形成されていることを確認した。
上記(1)〜(4)の手順を行い、三ハロゲン化ホウ素−カーボネート化合物(以下、「BF3−MCBA」という)を準備した。
<組成物の調製及び重合>
(5)上記(1)と同様の手順で準備を行った。
(6)窒素雰囲気とした反応容器を上記(5)のウォーターバスに設置し、表5の組成比率に従って、各原料を反応容器に添加し、撹拌することで組成物を調製した。
(7)上記(6)において調製した組成物を、表7の重合条件に従い重合することで、重合物を得た。
表3〜8の組成比率、及び重合条件とした以外は、実施例1と同様の方法により、組成物を調製し、重合物を得た。
なお、実施例24〜30、42〜45、52〜56では、評価を行うに辺り、重合性評価及び副反応性評価用のサンプルを封管された耐圧瓶内で用意した。
実施例1〜73で調製した組成物の評価結果を表7、8に示す。
表9、10の組成に従って、上記実施例1と同様の方法により、比較例1〜56の組成物を調製し、表11、12の重合条件に従って、重合物を得た。比較例23〜29、41〜44、51〜55では、評価を行うにあたり、重合性評価及び副反応性評価用のサンプルを封管された耐圧瓶内で用意した。比較例1〜56で調製した組成物の評価結果を表11、12に示す。
<重合物を塗付したガラス基板の準備>
(1)実施例66で得られた重合物を、同重量のジクロロメタン(和光純薬株式会社製)に溶解し、重合物溶液を得た。
なお、重合物を溶解するために用いる化合物は、特に限定されず、重合物を溶解させられ、且つ後の工程において除去できるものであれば良い。
(2)両面光学研磨された角型石英ガラス板(ジーエルサイエンス株式会社製、サイズ10mm×10mm、厚み1mm)上に、上記(1)の重合物溶液を滴下し、バーコーター(第一理化株式会社、番線の番号No.18)で約41μmに塗付した。
(3)真空乾燥器(東京理化器械株式会社製、VOS−451D、なお、真空ポンプには、アルバック機工株式会社製、小型油回転真空ポンプ GCD−201Xを用いた)に上記(2)で得られた石英ガラス板を入れ、室温、13Pa、24時間乾燥させた。
なお、乾燥する際の、温度、圧力は、特に限定されず、重合物溶液に含有される揮発物が急激に揮発しない条件を適宜選択すれば良い。本実施例においては、徐々に減圧を行い、最終的に13kPaとした。
(4)乾燥後の石英ガラス板上にある重合物塗布部の全光線透過率を、ヘーズメーター(日本電色工業株式会社製、NDH−5000W)を用い、測定した(ここで得られた全光線透過率を、「TLT0」という。)。本実施例では、全光線透過率は88%であった。
(5)乾燥後の石英ガラス板を、温度25℃、湿度60%RHに設定した恒温恒湿器(エスペック株式会社製、PSL−4J)に、300日間入れ、保持した。
(6)上記(5)で得られた石英ガラス板上にある重合物塗布部の全光線透過率を、上記(4)と同様に測定した(ここで得られた全光線透過率を、「TLT300」という。)。
(7)TLT300が、80%以上の場合に良好(「A」)と判断し、85%以上の場合に特に良好(「AA」)と判断し、これ以外の場合に不良(「C」)と判断した。本実施例では、TLT300が83%であったことから、良好と判断した。
(8)透明性の維持割合(以下、「dTLT」という。)を、下記式を用いて、算出した。
dTLT(%)=TLT300/TLT0×100
(9)透明性の維持割合が、90%以上の場合に良好(「A」)と判断し、95%以上の場合に特に良好(「AA」)と判断し、これ以外の場合に不良(「C」)と判断した。本実施例では、透明性の維持割合が、94%であったことから、良好と判断した。
(10)上記(7)及び(9)の評価において、同時に特に良好であると判断された場合、及び少なくとも1つの評価において良好と判断され、それ以外の評価において特に良好又は良好と判断された場合に、総合判定として合格((「AA」又は「A」)とした。それ以外の場合については、全て不合格(「C」)とした。
なお、本実施例では、TLT300が83%と良好(「A」)であり、dTLTが94%と良好(「A」)であり、両評価において共に良好であったことから、総合判定としては良好(「A」)と判断した。
表13に記載の実施例で得られた重合物を用いた以外は、実施例74と同様の方法により、重合物が塗付されたガラス基板を評価した。
<三ハロゲン化ホウ素−カーボネート化合物(BF3−MCBB−2)の調製>
(1)準備:マグネチックスターラー上に、投げ込み式冷却加熱ユニットが取り付けられたウォーターバスを載せ、そこに水及び攪拌子を入れた。投げ込み式冷却加熱ユニットを起動させ、水の温度が20℃となるように設定した。
(2)窒素雰囲気とした反応容器を上記(1)のウォーターバスに設置し、表14の組成比率に従って各原料を反応容器に添加し、1時間撹拌した。
(3)反応容器に減圧溜去装置を取り付け、徐々に減圧を行い、最終的に2kPaまで減圧し、4時間維持した。
(4)上記(3)で得られた反応液を用い、11B−NMRによる解析を行うことで、錯体が形成されていることを確認した。
上記(1)〜(4)の手順を行い、三ハロゲン化ホウ素−カーボネート化合物(以下、「BF3−MCBB−2」という)を調製した。
表14の組成比率とした以外は、調製例1と同様の方法により、三ハロゲン化ホウ素−カーボネート化合物を調製した。
<組成物の調製及び重合>
(1)準備:マグネチックスターラー上に、投げ込み式冷却加熱ユニットが取り付けられたウォーターバスを載せ、そこに水及び攪拌子を入れた。投げ込み式冷却加熱ユニットを起動させ、水の温度が20℃となるように設定した。
(2)窒素雰囲気とした反応容器を上記(1)のウォーターバスに設置し、表15の組成比率に従って、反応容器に添加し、撹拌することで組成物を調製した。
(3)上記(2)において調製した組成物を、表17の重合条件に従い重合することで、重合物を得た。
(4)真空乾燥器(東京理化器械株式会社製、VOS−451D、なお、真空ポンプには、アルバック機工株式会社製、小型油回転真空ポンプ GCD−201Xを用いた)に上記(3)で得られた重合物を入れ、50℃、13Pa、24時間乾燥させた。
(5)上記(4)で得られた重合物を、乾燥したガラス製容器に移し、重合物の重量を測定した(以下、「RGWS」という。)。
(6)恒温器(エスペック社製、IPHH−202)に入れ、窒素雰囲気とした後、器内温度を180℃として、1000時間保持した。
(7)上記(6)で得られた重合物の重量を測定した(以下、「RGWF」という。)。
(8)重合物の重量変化(以下、「RGW」という。)を、以下の式により算出した。
RGW(%)=100−RGWF/RGWS×100
(9)RGWが、5%以下の場合に良好(「A」)と判断し、2%以下の場合に特に良好(「AA」)と判断し、これ以外の場合に不良(「C」)と判断した。本実施例では、RGWが5%であったことから、良好と判断した。
恒温器の器内温度を250℃とした以外は、RA法と同様に行った。
表15、16の組成比率、及び表17、18の重合条件とした以外は、実施例79と同様の方法により、重合物を得た。実施例79〜141で得られた重合物の評価結果を表17、18に示す。
なお、実施例95〜101、108〜115では、重合物を封管された耐圧瓶内で用意した。
<三ハロゲン化ホウ素−カーボネート化合物(BF3−MCBD−1)の準備>
(1)準備:マグネチックスターラー上に、投げ込み式冷却加熱ユニットが取り付けられたウォーターバスを載せ、そこに水及び攪拌子を入れた。投げ込み式冷却加熱ユニットを起動させ、水の温度が20℃となるように設定した。
(2)窒素雰囲気とした反応容器を上記(1)のウォーターバスに設置し、4−メチル−1,3−ジオキソラン−2−オン42質量%、三フッ化ホウ素ジエチルエーテル錯体58質量%を、反応容器に添加し、1時間撹拌した。
(3)反応容器に減圧溜去装置を取り付け、徐々に減圧を行い、最終的に2kPaまで減圧し、4時間維持した。
(4)上記(3)で得られたものを用い、11B−NMRによる解析を行うことで、錯体が形成されていることを確認した。
(5)上記(1)と同様の手順で準備を行った。
(6)窒素雰囲気とした反応容器を上記(5)のウォーターバスに設置し、表19の組成比率に従って、反応容器に添加し、撹拌することで組成物を調製した。
(7)上記(6)において調製した組成物を、表22の重合条件に従い重合することで、重合物を得た。
なお、混合指標γは、以下の式(10)により算出した。
指標γ=αd/αt×100 (10)
ここで、
αd:(D)連鎖移動剤の物質量(mol)
αt:(C)エピスルフィド化合物に含まれるエピスルフィド基の物質量(mol)、をそれぞれ示す。
(8)上記(7)で得られた重合物のエピスルフィド基反応率を、表22の方法により測定し、元となるエピスルフィド化合物中のエピスルフィド基が重合していることを確認した。
(9)重合物の耐熱安定性評価を、表22の方法により評価した。
表19〜21の組成比率、及び表22〜24の重合条件とした以外は、実施例142と同様の方法により、重合物を得た。実施例142〜247で得られた重合物の評価結果を表22〜24に示す。
なお、実施例164〜170、177〜191、198〜205では、重合物を封管された耐圧瓶内で用意した。
Claims (13)
- (A)カーボネート化合物と、(B)三ハロゲン化ホウ素と、(C)エピスルフィド化合物と、を含有する組成物。
- 前記カーボネート化合物の炭素数が、3〜25である、請求項1又は2記載の組成物。
- 前記カーボネート化合物のカーボネート基の数が、1〜4である、請求項1〜3のいずれか一項に記載の組成物。
- 前記(A)カーボネート化合物及び前記(B)三ハロゲン化ホウ素の少なくとも一部が錯体を形成している、請求項1〜4のいずれか一項に記載の組成物。
- 下記式(2)で表される、前記(A)カーボネート化合物と前記(B)三ハロゲン化ホウ素との比率を表す指標αが1〜1000である、請求項1〜5のいずれか一項に記載の組成物。
指標α=αc/αb (2)
αc:前記カーボネート化合物のカーボネート基の物質量(mol)
αb:前記三ハロゲン化ホウ素の物質量(mol) - 前記三ハロゲン化ホウ素が、三フッ化ホウ素、三塩化ホウ素、及び三臭化ホウ素からなる群より選ばれる少なくとも1種である、請求項1〜6のいずれか一項に記載の組成物。
- 前記エピスルフィド化合物が、3員環チオエーテル構造のみを重合性官能基として有する化合物である、請求項1〜7のいずれか一項に記載の組成物。
- 前記三ハロゲン化ホウ素の物質量(mol)と、前記エピスルフィド化合物に含まれるエピスルフィド基の物質量(mol)との比が、1:10〜1:100000である、請求項1〜8のいずれか一項に記載の組成物。
- 前記エピスルフィド化合物のエピスルフィド当量が、65〜700g/molである、請求項1〜9のいずれか一項に記載の組成物。
- 請求項1〜11のいずれか一項に記載の組成物中の前記エピスルフィド化合物を重合して形成される、重合物。
- 請求項1〜11のいずれか一項に記載の組成物中の前記エピスルフィド化合物を加熱及び/又はエネルギー線照射により重合する、重合物を製造する方法。
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