JP2014136781A - 組成物及び重合物 - Google Patents
組成物及び重合物 Download PDFInfo
- Publication number
- JP2014136781A JP2014136781A JP2013007488A JP2013007488A JP2014136781A JP 2014136781 A JP2014136781 A JP 2014136781A JP 2013007488 A JP2013007488 A JP 2013007488A JP 2013007488 A JP2013007488 A JP 2013007488A JP 2014136781 A JP2014136781 A JP 2014136781A
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- JP
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- Prior art keywords
- compound
- epoxy
- bis
- lactone
- epoxypropyl
- 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
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- 239000000203 mixture Substances 0.000 title claims abstract description 201
- 229920000642 polymer Polymers 0.000 title claims abstract description 104
- 150000001875 compounds Chemical class 0.000 claims abstract description 370
- -1 ester compound Chemical class 0.000 claims abstract description 339
- 239000004593 Epoxy Substances 0.000 claims abstract description 299
- 229910052796 boron Inorganic materials 0.000 claims abstract description 128
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims abstract description 126
- 239000000126 substance Substances 0.000 claims description 120
- 125000003700 epoxy group Chemical group 0.000 claims description 85
- 125000000524 functional group Chemical group 0.000 claims description 29
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 24
- 125000004122 cyclic group Chemical group 0.000 claims description 24
- 230000000379 polymerizing effect Effects 0.000 claims description 24
- 125000001931 aliphatic group Chemical group 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 19
- 125000004185 ester group Chemical group 0.000 claims description 19
- 238000010438 heat treatment Methods 0.000 claims description 16
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 15
- 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
- 150000004292 cyclic ethers Chemical group 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 claims description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 5
- 238000006116 polymerization reaction Methods 0.000 description 76
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 61
- 239000000047 product Substances 0.000 description 60
- 238000000034 method Methods 0.000 description 59
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 52
- 239000012986 chain transfer agent Substances 0.000 description 42
- 238000006243 chemical reaction Methods 0.000 description 42
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 37
- 238000011156 evaluation Methods 0.000 description 35
- 150000002148 esters Chemical class 0.000 description 34
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 29
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 29
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 28
- 239000000463 material Substances 0.000 description 27
- 238000000576 coating method Methods 0.000 description 26
- 239000011248 coating agent Substances 0.000 description 25
- 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 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 238000002360 preparation method Methods 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
- 238000005481 NMR spectroscopy Methods 0.000 description 18
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 18
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 17
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 17
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 16
- 239000012299 nitrogen atmosphere Substances 0.000 description 16
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 15
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 15
- 239000002994 raw material Substances 0.000 description 15
- 230000001588 bifunctional effect Effects 0.000 description 14
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 14
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N dimethylmethane Natural products CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 14
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 14
- 238000012986 modification Methods 0.000 description 14
- 230000004048 modification Effects 0.000 description 14
- 229920003986 novolac Polymers 0.000 description 14
- 239000001294 propane Substances 0.000 description 14
- 239000000853 adhesive Substances 0.000 description 13
- 150000001412 amines Chemical group 0.000 description 13
- 150000007942 carboxylates Chemical class 0.000 description 13
- 238000004821 distillation Methods 0.000 description 13
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 13
- 230000003287 optical effect Effects 0.000 description 13
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound 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
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 12
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 12
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 12
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 12
- 230000001070 adhesive effect Effects 0.000 description 12
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 12
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 12
- 238000005260 corrosion Methods 0.000 description 11
- 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 11
- 125000001033 ether group Chemical group 0.000 description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
- AOGQPLXWSUTHQB-UHFFFAOYSA-N hexyl acetate Chemical compound CCCCCCOC(C)=O AOGQPLXWSUTHQB-UHFFFAOYSA-N 0.000 description 11
- 150000002430 hydrocarbons Chemical group 0.000 description 11
- 238000005259 measurement Methods 0.000 description 11
- 238000002156 mixing Methods 0.000 description 11
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 10
- 125000002723 alicyclic group Chemical group 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
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 10
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 10
- 238000001816 cooling Methods 0.000 description 10
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 10
- ZOCHHNOQQHDWHG-UHFFFAOYSA-N hexan-3-ol Chemical compound CCCC(O)CC ZOCHHNOQQHDWHG-UHFFFAOYSA-N 0.000 description 10
- JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 description 10
- 150000002989 phenols Chemical class 0.000 description 10
- 229920001296 polysiloxane Polymers 0.000 description 10
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 10
- 239000011593 sulfur Substances 0.000 description 10
- 229910052717 sulfur Inorganic materials 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 compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
- 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 9
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 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
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 9
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 9
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 9
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 8
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 8
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- FZXRXKLUIMKDEL-UHFFFAOYSA-N 2-Methylpropyl propanoate Chemical compound CCC(=O)OCC(C)C FZXRXKLUIMKDEL-UHFFFAOYSA-N 0.000 description 8
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 8
- XSIFPSYPOVKYCO-UHFFFAOYSA-N butyl benzoate Chemical compound CCCCOC(=O)C1=CC=CC=C1 XSIFPSYPOVKYCO-UHFFFAOYSA-N 0.000 description 8
- 239000002131 composite material Substances 0.000 description 8
- 230000007797 corrosion Effects 0.000 description 8
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 8
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- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 8
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- 239000000314 lubricant Substances 0.000 description 8
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 8
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- 238000005292 vacuum distillation Methods 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 7
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- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 7
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 7
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 7
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 7
- 239000007983 Tris buffer Substances 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 239000012964 benzotriazole Substances 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 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 7
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 7
- 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 7
- 239000011521 glass Substances 0.000 description 7
- QNVRIHYSUZMSGM-UHFFFAOYSA-N hexan-2-ol Chemical compound CCCCC(C)O QNVRIHYSUZMSGM-UHFFFAOYSA-N 0.000 description 7
- 238000009413 insulation Methods 0.000 description 7
- 238000012423 maintenance Methods 0.000 description 7
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- 239000002184 metal Substances 0.000 description 7
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- 239000003973 paint Substances 0.000 description 7
- 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 7
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- 239000002685 polymerization catalyst Substances 0.000 description 7
- 238000002834 transmittance Methods 0.000 description 7
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 6
- ZGXMNEKDFYUNDQ-GQCTYLIASA-N (5e)-hepta-1,5-diene Chemical compound C\C=C\CCC=C ZGXMNEKDFYUNDQ-GQCTYLIASA-N 0.000 description 6
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 6
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- ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 2-octanone Chemical compound CCCCCCC(C)=O ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 0.000 description 6
- HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 description 6
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 6
- 229940126062 Compound A Drugs 0.000 description 6
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 6
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 6
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 6
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 6
- FFOPEPMHKILNIT-UHFFFAOYSA-N Isopropyl butyrate Chemical compound CCCC(=O)OC(C)C FFOPEPMHKILNIT-UHFFFAOYSA-N 0.000 description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 6
- 229940064734 aminobenzoate Drugs 0.000 description 6
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 6
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 6
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Abstract
【解決手段】本発明は、(A)エステル化合物と、(B)三ハロゲン化ホウ素と、(C)エポキシ化合物と、を含有し、(A)エステル化合物及び(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組成物に関する。
【選択図】なし
Description
[1]
(A)エステル化合物と、(B)三ハロゲン化ホウ素と、(C)エポキシ化合物と、を含有し、(A)エステル化合物及び(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、組成物。
[2]
(A)エステル化合物が、下記式(1)又は(2)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は、水素原子、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、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く、
R3及びR4は、それぞれ独立に、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置換芳香族炭化水素基を示し、R3及びR4は、互いに連結されていてもよい。]
[3]
(A)エステル化合物の炭素数が、3〜26である、項[1]又は[2]記載の組成物。
[4]
(A)エステル化合物のエステル基の数が、1〜8である、項[1]〜[3]のいずれか一項に記載の組成物。
[5]
下記式(3)で表される(A)エステル化合物と(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]〜[4]のいずれか一項に記載の組成物。
指標α=αs/αb (3)
αs:(A)エステル化合物のエステル基の物質量(mol)
αb:(B)三ハロゲン化ホウ素の物質量(mol)
[6]
(B)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]〜[5]のいずれか一項に記載の組成物。
[7]
(C)エポキシ化合物が、3員環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]〜[6]のいずれか一項に記載の組成物。
[8]
(B)三ハロゲン化ホウ素の物質量(mol)と、(C)エポキシ化合物に含まれるエポキシ基の物質量(mol)との比が、1:10〜1:100000である、項[1]〜[7]のいずれか一項に記載の組成物。
[9]
(C)エポキシ化合物のエポキシ当量が、55〜600g/molである、項[1]〜[8]のいずれか一項に記載の組成物。
[10]
(C)エポキシ化合物が、下記式(4)、(5)、(6)又は(7)で表される部分構造を有する、項[1]〜[9]のいずれか一項に記載の組成物。
[式中、R10、R11、R12、R13、R14、R15、R16、R17、R18、R19、R20、R21、R22、R23及びR24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。]
[11]
項[1]〜[10]のいずれか一項に記載の組成物中の(C)エポキシ化合物を重合して形成される、重合物。
[12]
項[1]〜[10]のいずれか一項に記載の組成物中の(C)エポキシ化合物を加熱及び/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)エステル化合物(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)エポキシ化合物(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)、(C)及び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、エステル基を分子内に1つ以上含有するエステル化合物である。成分(A)として、1種のエステル化合物を単独で用いてもよいし、複数種のエステル化合物を組み合わせて用いてもよい。
本実施形態に係る単官能エステル化合物は、エステル基を1つ有する化合物であれば、特に限定されない。単官能エステル化合物は、上記式(1)において、aが1の場合であり、より具体的に例示するならば、下記式(8)で示される。
本実施形態に係る隣接2官能エステル化合物は、エステル基を2つ有し、エステル基同士が隣接した構造(直接結合した構造)を有する化合物であれば、特に限定されない。隣接2官能エステル化合物は、具体的には上記式(2)で表される化合物が挙げられる。
本実施形態に係る間接2官能エステル化合物は、エステル基を2つ有し、エステル基同士が隣接していない化合物であれば、特に限定されない。間接2官能エステル化合物は、具体的には上記式(1)において、aが2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エステル化合物は、エステル基を3つ以上有し、エステル基同士が隣接していない化合物であれば、特に限定されない。多官能エステル化合物は、具体的には上記式(1)において、aが3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種のエポキシ化合物を単独で用いてもよいし、複数種のエポキシ化合物を組み合わせて用いてもよい。
単官能エポキシ化合物は、3員環エーテル構造を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、エチレンオキシド、プロピレンオキシド、1−ブテンオキシド、2−ブテンオキシド、ブタジエンオキシド、ブタジエンジエポキシド、シクロブテンオキシド、1,3−シクロブタジエンジエポキシド、1−ペンテンオキシド、2−ペンテンオキシド、1,3−ペンタジエンジエポキシド、1,4−ペンタジエンジエポキシド、2−メチル−2−ブテンオキシド、2−メチル−3−ブテンオキシド、シクロペンテンオキシド、1,3−シクロペンタジエンジエポキシド、1−メチル−シクロブテンオキシド、3−メチル−1−シクロブテンオキシド、1−ヘキセンオキシド、2−ヘキセンオキシド、3−ヘキセンオキシド、1,3−ヘキサジエンジエポキシド、1,4−ヘキサジエンジエポキシド、1,5−ヘキサジエンジエポキシド、1,3,5−ヘキサトリエントリエポキシド、シクロヘキセンオキシド、1,3−シクロヘキサジエンジエポキシド、1,3,5−シクロヘキサトリエントリエポキシド、1−メチル−シクロペンテンオキシド、3−メチル−シクロペンテンオキシド、1−メチル−1,3−シクロペンタジエンジエポキシド、2−メチル−1,3−シクロペンタジエンジエポキシド、5−メチル−1,3−シクロペンタジエンジエポキシド、3,4−ジメチル−シクロブテンオキシド、2,3−ジメチル−シクロブテンオキシド、1,2−ジメチル−シクロブテンオキシド、1,2−ジメチル−1,3−シクロブタジエンジエポキシド、2,3−ジメチル−1,3−シクロブタジエンジエポキシド、3,3−ジメチル−1,2−エポキシブタン、1−ヘプテンオキシド、2−ヘプテンオキシド、3−ヘプテンオキシド、1,3−ヘプタジエンジエポキシド、1,4−ヘプタジエンジエポキシド、1,5−ヘプタジエンジエポキシド、1,5−ヘプタジエンジエポキシド、1,6−ヘプタジエンジエポキシド、1,3,5−ヘプタトリエントリエポキシド、1,3,6−ヘプタトリエントリエポキシド、1,4,6−ヘプタトリエントリエポキシド、シクロヘプテンオキシド、1−メチル−シクロヘキセンオキシド、3−メチル−シクロヘキセンオキシド、4−メチル−シクロヘキセンオキシド、1−メチル−1,3−シクロヘキサジエンジエポキシド、1−メチル−1,4−ヘキサジエンジエポキシド、1−メチル−1,3,5−ヘキサトリエントリエポキシド、1,2−エポキシ−5−ヘキセン、1,2−エポキシ−4−ビニルシクロヘキセン、2−ノルボルネンオキシド、7−メチル−2−ノルボルネンオキシド、7,7−ジメチル−2−ノルボルネンオキシド、2−メチル−2−ノルボルネンオキシド、2,3−ジメチル−2−ノルボルネンオキシド、2,7−ジメチル−2−ノルボルネンオキシド、2,7,7−トリメチル−2−ノルボルネンオキシド、2,3−エポキシ−ビシクロ[2.2.2]オクタン、2,3−エポキシ−2−メチル−ビシクロ[2.2.2]オクタン、2,3−エポキシ−2,3−ジメチル−ビシクロ[2.2.2]オクタン、2,3−エポキシ−2,5−ジメチル−ビシクロ[2.2.2]オクタン、2,3−エポキシ−2,6−ジメチル−ビシクロ[2.2.2]オクタン、2,3−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−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−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、エポキシヘキサヒドロフタル酸ジオクチル、エポキシヘキサヒドロフタル酸ジ−2−エチルヘキシル、スチルベンオキシド、フェニル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−エポキシプロパン、ピネンオキシド、イソプレンモノオキシド、1,2−エポキシエチルベンゼン、ナフチルグリシジルエーテル、3−(2−ビフェニロキシ)−1,2−エポキシプロパン、アリルグリシジルエーテル、1,1−ジフェニル−エチレンオキシド、グリシジル(メタ)アクリレート、グリシジルブチレート、ヨードメチルオキシラン、4−(2,3−エポキシプロピル)モルフォリン、グリシジルメチルエーテル、2−フェニル−プロピレンオキシド、2,3−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オキシド、エチル−3−フェニルグリシデート、リモネンオキシド、エポキシスクシン酸、3−グリシドキシプロピルトリメトキシシラン、(3−グリシドキシプロピル)ペンタメチルジシロキサン、3−グリシドキシプロピル(メチル)ジメトキシシラン、3−グリシドキシプロピル(メチル)ジエトキシシラン、3−グリシドキシプロピル(メチル)ジブトキシシラン、2−(3,4−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−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−エポキシプロピル(メチル)ジメトキシシラン、2,3−エポキシプロピル(フェニル)ジメトキシシラン、3−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−グリシドキシプロピルトリブトキシシラン、2−(3,4−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−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−エポキシプロピルトリメトキシシラン及び2,3−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グリシジルエーテル化物である多官能エポキシ化合物は、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グリシジルエーテル化物から選ばれ得る。
脂環式エポキシ化合物は、脂環式エポキシ構造を有するエポキシ化合物であれば、特に限定されるものではなく、例えば、シクロヘキセンオキシド基、トリシクロデセンオキシド基又はシクロペンテンオキシド基等を有するエポキシ化合物から選ばれ得る。
ノボラック化合物のグリシジルエーテル化物である多官能エポキシ化合物は、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グリシジルエーテル化物から選ばれ得る。
芳香族エポキシ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。
複素環式エポキシ化合物は、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ポキシ化合物から選ばれ得る。
グリシジルエステル系エポキシ化合物は、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ポキシ化合物から選ばれ得る。
グリシジルアミン系エポキシ化合物は、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グリシジル化したエポキシ化合物から選ばれ得る。
ハロゲン化フェノール類をグリシジル化したエポキシ化合物は、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グリシジルエーテル化したエポキシ化合物から選ばれ得る。
多官能脂肪族エポキシ化合物としては、特に限定されるものではなく、具体的には、1,1−ビスエポキシメタン、1−エポキシ−1−(2,3−エポキシプロピル)メタン、1,1−ビス(2,3−エポキシプロピル)メタン、1−エポキシ−1−(2,3−エポキシプロピル)エタン、1,2−ビス(2,3−エポキシプロピル)エタン、1−エポキシ−3−(2,3−エポキシプロピル)ブタン、1,3−ビス(2,3−エポキシプロピル)プロパン、1−エポキシ−4−(2,3−エポキシプロピル)ペンタン、1,4−ビス(2,3−エポキシプロピル)ブタン、1−エポキシ−5−(2,3−エポキシプロピル)ヘキサン、1−エポキシ−2−(γ−エポキシブチルチオ)エタン、1−エポキシ−2−[2−(γ−エポキシブチルチオ)エチルチオ]エタン、テトラキス(2,3−エポキシプロピル)メタン、1,1,1−トリス(2,3−エポキシプロピル)プロパン、1,1,3−トリス(2,3−エポキシプロピル)−2−チアプロパン、1,2,4,5−ビス(2,3−エポキシプロピル)−3−チアペンタン、1,3または1,4−ビスエポキシシクロヘキサン、1,3または1,4−ビス(2,3−エポキシプロピル)シクロヘキサン、2,5−ビスエポキシ−1,4−ジチアン、2,5−ビス(2,3−エポキシプロピル)−1,4−ジチアン、4−エポキシ−1、2−シクロヘキセンオキシド、2,2−ビス[4−エポキシシクロヘキシル]プロパン、2,2−ビス[4−(2,3−エポキシプロピル)シクロヘキシル]プロパン、ビス[4−エポキシシクロヘキシル]メタン、ビス[4−(2,3−エポキシプロピル)シクロヘキシル]メタン、ビス[4−(2,3−エポキシプロピル)シクロヘキシル]スルフィド、ビス[4−エポキシシクロヘキシル]スルフィド、ビス(2,3−エポキシプロピル)エーテル、ビス[(2,3−エポキシプロピル)オキシ]メタン、1,2−ビス[(2,3−エポキシプロピル)オキシ]エタン、1,3−ビス[(2,3−エポキシプロピル)オキシ]プロパン、1,2−ビス[(2,3−エポキシプロピル)オキシ]プロパン、1−[(2,3−エポキシプロピル)オキシ]−2−[(2,3−エポキシプロピル)オキシメチル]プロパン、1,4−ビス[(2,3−エポキシプロピル)オキシ]ブタン、1,3−ビス[(2,3−エポキシプロピル)オキシ]ブタン、1−[(2,3−エポキシプロピル)オキシ]−3−[(2,3−エポキシプロピル)オキシメチル]ブタン、1,5−ビス[(2,3−エポキシプロピル)オキシ]ペンタン、1−[(2,3−エポキシプロピル)オキシ]−4−[(2,3−エポキシプロピル)オキシメチル]ペンタン、1,6−ビス[(2,3−エポキシプロピル)オキシ]ヘキサン、1−[(2,3−エポキシプロピル)オキシ]−5−[(2,3−エポキシプロピル)オキシメチル]ヘキサン、1−[(2,3−エポキシプロピル)オキシ]−2−{[2−(2,3−エポキシプロピル)オキシエチル)オキシ]エタン、1−[(2,3−エポキシプロピル)オキシ)−2−{[2−(2−(2,3−エポキシプロピル)オキシエチル)オキシエチル]オキシ}エタン、テトラキス[(2,3−エポキシプロピル)オキシメチル]メタン、1,1,1−トリス[(2,3−エポキシプロピル)オキシメチル)プロパン、1,5−ビス[(2,3−エポキシプロピル)オキシ]−2−[(2,3−エポキシプロピル)オキシメチル]−3−チアペンタン、1,5−ビス[(2,3−エポキシプロピル)オキシ]−2,4−ビス[(2,3−エポキシプロピル)オキシメチル]−3−チアペンタン;
分子内にエポキシ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(9)で表される化合物から選ばれ得る。
(R40R41R42SiO1/2)a(R43R44SiO2/2)b(R45SiO3/2)c(SiO4/2)d (9)
異種重合性官能基含有エポキシ化合物は、特に限定されるものではなく、例えば下記式(10)で表される化合物から選ばれ得る。
指標α=αs/αb (3)
αs:(A)エステル化合物のエステル基の物質量(mol)
αb:(B)三ハロゲン化ホウ素の物質量(mol)
指標β=αb/αep×100 (11)
αb:(B)三ハロゲン化ホウ素の物質量(mol)
αep:(C)エポキシ化合物に含まれるエポキシ基の物質量(mol)
(B)三ハロゲン化ホウ素の物質量(mol)と、(C)エポキシ化合物に含まれるエポキシ基の物質量(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)エポキシ化合物に含まれるエポキシ基の物質量(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)エポキシ化合物に含まれるエポキシ基の物質量(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)エポキシ化合物に含まれるエポキシ基の物質量(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)エポキシ化合物に含まれるエポキシ基の物質量(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)エポキシ化合物に含まれるエポキシ基の物質量(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)エポキシ化合物に含まれるエポキシ基の物質量(mol)との比が1:10000であるとき、指標β=0.01となる。
環状カーボネート化合物は、環状構造内にカーボネート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。
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/αep×100 (12)
αd:(D)連鎖移動剤の物質量(mol)
αep:(C)エポキシ化合物に含まれるエポキシ基の物質量(mol)
(D)連鎖移動剤の物質量(mol)と、(C)エポキシ化合物に含まれるエポキシ基の物質量(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)エポキシ化合物に含まれるエポキシ基の物質量(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)エポキシ化合物に含まれるエポキシ基の物質量(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)エポキシ化合物に含まれるエポキシ基の物質量(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)エポキシ化合物に含まれるエポキシ基の物質量(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に調製した。
(2)サンプル瓶に、三ハロゲン化ホウ素−エステル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に調製した。
(3)サンプル瓶に、調製した三ハロゲン化ホウ素−エステル化合物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に調製した。
(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−エステル化合物では錯体が形成されていると判断した。
「JIS K7236:2001(エポキシ樹脂のエポキシ当量の求め方)」に従って測定した。
混合指標αは、以下の式(3)により算出した。
指標α=αs/αb (3)
ここで、
αs:(A)エステル化合物のエステル基の物質量(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(11)により算出した。
指標β=αb/αep×100 (11)
ここで、
αb:(B)三ハロゲン化ホウ素の物質量(mol)
αep:(C)エポキシ化合物に含まれるエポキシ基の物質量(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に調製した。
・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:1000回
上記測定結果から、以下の手順で、エポキシ基反応率を算出した。
(3)1H−NMRチャートから、エポキシ基由来ピークの面積値を算出した。
ここで、エポキシ基由来のピークとは、エポキシ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。エポキシ化合物を構成するエポキシ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、エポキシ基反応率(%)を求めた。
エポキシ基反応率(%)=100−EPOA×(TBEG/TBEM)×(2/TBEA)×(REAG/SAMG)×(WPE/EPOG)×100
EPOA:エポキシ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
EPOG:組成物を調製する際に使用したエポキシ化合物の重量(g)
WPE:組成物を調製する際に使用したエポキシ化合物のエポキシ当量(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ポキシ化合物中のエポキシ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、エポキシ基反応率(%)を求めた。
エポキシ基反応率(%)=100−{EPOA/(エポキシ基由来ピークを構成している水素の個数)}×(TBEG/TBEM)×(2/TBEA)×(REAG/SAMG)×(WPE/EPOG)×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法によりエポキシ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、以下の手順でエポキシ基反応率を算出した。
(4)FT−IRチャートから、エポキシ基由来ピークの面積値を算出した。
ここで、エポキシ基由来のピークとは、エポキシ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、エポキシ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、エポキシ基反応率(%)を求めた。
エポキシ基反応率(%)=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、エポキシ基由来のピーク面積
SIRA:サンプルを作製する際に用いた、重合前のエポキシ化合物を測定した結果得られたFT−IRチャートにおける、エポキシ基由来のピーク面積。
調製した組成物の一部を、20℃に設定された恒温器に入れ、24時間保持した後、EA法にてエポキシ基反応率を算出した。
安定性は、エポキシ基反応率が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法にてエポキシ基反応率を算出した。
安定性は、エポキシ基反応率が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ポキシ基反応率を算出した。
重合性は、エポキシ基反応率が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法にてエポキシ基反応率を算出した。
重合性は、エポキシ基反応率が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。
以下の手順に従い、黄色度(YI)を測定した。
なお、YIは、“ASTM D1925−70(1988):Test Method for Yellowness Index of Plastics”に準じて求めた。
(1)調製した組成物の一部を、短光路分解セル(スターナ社製、開放型Type20/O、12.5mm×3.5mm×45mm、光路長1mm)に入れ、当該組成物の重合性評価を行う条件と同一の温度・時間にて、重合した。
なお、重合性評価において、封管した耐圧瓶内で重合物を用意したものに関しては、以下の手順で評価用のサンプルを準備した。
(2−1)耐圧瓶内から重合物を取出し、同重量のジクロロメタン(和光純薬工業株式会社製)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。
(2−2)得られた重合物溶液を短光路分解セル(スターナ社製、開放型Type20/O、12.5mm×3.5mm×45mm、光路長1mm)に入れた。
(2−3)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(2−2)で得られたセルを入れ、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、常圧から徐々に減圧を行い、最終的に13kPaとした。
(3)(1)又は(2−3)で得られた重合物を内包したセルを、下記の機器にてYIを測定した。
分光色彩計:日本電色工業株式会社製「SD5000」(積分球開口部を直径10mmに改造)
透明性は、YI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、重合性評価、透明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A:エチレンオキシド(Aldrich社製、以下、「EPO−1」という。)
・エポキシ当量(WPE):44g/eq.
(2)エポキシ化合物B:プロピレンオキシド(和光純薬工業株式会社製、以下、「EPO−2」という。)
・エポキシ当量(WPE):58g/eq.
(3)エポキシ化合物C:1,2−エポキシブタン(東京化成工業株式会社製、以下、「EPO−3」という。)
・エポキシ当量(WPE):72g/eq.
(4)エポキシ化合物D:1,2−エポキシペンタン(東京化成工業株式会社製、以下、「EPO−4」という。)
・エポキシ当量(WPE):86g/eq.
(5)エポキシ化合物E:1,2−エポキシヘキサン(東京化成工業株式会社製、以下、「EPO−5」という。)
・エポキシ当量(WPE):100g/eq.
(6)エポキシ化合物F:1,2−エポキシヘプタン(東京化成工業株式会社製、以下、「EPO−6」という。)
・エポキシ当量(WPE):114g/eq.
(7)エポキシ化合物G:1,2−エポキシオクタン(和光純薬工業株式会社製、以下、「EPO−7」という。)
・エポキシ当量(WPE):128g/eq.
(8)エポキシ化合物H:1,2−エポキシデカン(和光純薬工業株式会社製、以下、「EPO−8」という。)
・エポキシ当量(WPE):156g/eq.
(9)エポキシ化合物I:1,2−エポキシドデカン(和光純薬工業株式会社製、以下、「EPO−9」という。)
・エポキシ当量(WPE):184g/eq.
(10)エポキシ化合物J: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、「EPO−10」という。)
・エポキシ当量(WPE):212g/eq.
(11)エポキシ化合物K: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、「EPO−11」という。)
・エポキシ当量(WPE):240g/eq.
(12)エポキシ化合物L: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、「EPO−12」という。)
・エポキシ当量(WPE):268g/eq.
(13)エポキシ化合物M:1,2−エポキシエイコサン(東京化成工業株式会社製、以下、「EPO−13」という。)
・エポキシ当量(WPE):297g/eq.
(14)エポキシ化合物N: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、「EPO−14」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、「EPO−15」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、「EPO−16」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、「EPO−17」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):450g/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、「EPO−18」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.
(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、「EPO−19」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.
(20)エポキシ化合物T:ビスフェノールA型エポキシ化合物(以下、「EPO−20」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.
(21)エポキシ化合物U:シクロペンテンオキシド(Aldrich社製、以下、「EPO−21」という。)
・エポキシ当量(WPE):84g/eq.
(22)エポキシ化合物V:シクロヘキセンオキシド(Aldrich社製、以下、「EPO−22」という。)
・エポキシ当量(WPE):98g/eq.
(23)エポキシ化合物W:シクロヘプテンオキシド(Aldrich社製、以下、「EPO−23」という。)
・エポキシ当量(WPE):112g/eq.
(24)エポキシ化合物X:シクロオクテンオキシド(Aldrich社製、以下、「EPO−24」という。)
・エポキシ当量(WPE):126g/eq.
(25)エポキシ化合物Y:脂環式エポキシ化合物(以下、「EPO−25」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.
(26)エポキシ化合物Z:ビス(2,3−エポキシプロピル)ジスルフィド(以下、「EPO−26」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.
(27)エポキシ化合物AA: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、「EPO−27」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.
(28)エポキシ化合物AB: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、「EPO−28」という。)
・商品名:Gelest, Inc.、「SIB1092.0」
・エポキシ当量(WPE):192g/eq.
(29)エポキシ化合物AC: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、「EPO−29」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.
(30)エポキシ化合物AD: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、「EPO−30」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.
(31)エポキシ化合物AE:ブタジエンモノオキシド(和光純薬工業株式会社製、以下、「EPO−31」という。)
・エポキシ当量(WPE):70g/eq.
(32)エポキシ化合物AF:1,2−エポキシ−5−ヘキセン(和光純薬株式会社製、以下、「EPO−32」という。)
・エポキシ当量(WPE):98g/eq.
(33)エポキシ化合物AG:アリルグリシジルエーテル(和光純薬株式会社製、以下、「EPO−33」という。)
・エポキシ当量(WPE):114g/eq.
(34)エポキシ化合物AH:1,2−エポキシ−4−ビニルシクロヘキサン(Aldrich社製、以下、「EPO−34」という。)
・エポキシ当量(WPE):124g/eq.
(35)エポキシ化合物AI:グリシジルメタクリレート(和光純薬株式会社製、以下、「EPO−35」という。)
・エポキシ当量:142g/eq.
(36)エステル化合物A:メチルエタノアート(和光純薬工業株式会社製、以下、「MSCA」という。別名として、酢酸メチル、とも表現される。)
(37)エステル化合物B:エチルエタノアート(和光純薬工業株式会社製、以下、「MSCB」という。別名として、酢酸エチル、とも表現される。)
(38)エステル化合物C:ブチロ−4−ラクトン(和光純薬工業株式会社製、以下、「MSCC」という。別名として、γ−ブチロラクトン、とも表現される。)
(39)エステル化合物D:エチルプロパノアート(和光純薬工業株式会社製、以下、「MSCD」という。)
(40)エステル化合物E:ペンタノ−4−ラクトン(和光純薬工業株式会社製、以下、「MSCE」という。別名として、γ−バレロラクトン、とも表現される。)
(41)エステル化合物F:ペンタノ−5−ラクトン(東京化成工業株式会社製、以下、「MSCF」という。別名として、δ−バレロラクトン、とも表現される。)
(42)エステル化合物G:プロピルプロパノアート(和光純薬工業株式会社製、以下、「MSCG」という。)
(43)エステル化合物H:tert−ブチルエタノアート(和光純薬工業株式会社製、以下、「MSCH」という。別名として、tert−ブチルアセテート、とも表現される。)
(44)エステル化合物I:イソブチルプロパノアート(和光純薬工業株式会社製、以下、「MSCI」という。)
(45)エステル化合物J:ヘキシルエタノアート(和光純薬工業株式会社製、以下、「MSCJ」という。別名として、酢酸ヘキシル、とも表現される。)
(46)エステル化合物K:プロピルヘキサノアート(和光純薬工業株式会社製、以下、「MSCK」という。)
(47)エステル化合物L:シクロヘキシルブタノアート(和光純薬工業株式会社製、以下、「MSCL」という。)
(48)エステル化合物M:エチルデカノアート(和光純薬工業株式会社製、以下、「MSCM」という。)
(49)エステル化合物N:ドデシルエタノアート(和光純薬工業株式会社製、以下、「MSCN」という。別名として、酢酸ドデシル、とも表現される。)
(50)エステル化合物O:オクタデシルエタノアート(和光純薬工業株式会社製、以下、「MSCO」という。別名として、酢酸オクタデシル、とも表現される。)
(51)エステル化合物P:エチルドコサノアート(Aldrich社製、以下、「MSCP」という。)
(52)エステル化合物Q:ジメチルオキサレート(和光純薬工業株式会社製、以下、「MSCQ」という。)
(53)エステル化合物R:ジメチル−1,3−プロパンジオアート(東京化成工業株式会社製、以下、「MSCR」という。別名として、ジメチルマロネート、とも表現される。)
(54)エステル化合物S:ジメチル−1,4−ブタンジオアート(東京化成工業株式会社製、以下、「MSCS」という。別名として、ジメチルスクシネート、とも表現される。)
(55)エステル化合物T:ジエチル−1,4−ブタンジオアート(東京化成工業株式会社製、以下、「MSCT」という。別名として、ジエチルスクシネート、とも表現される。)
(56)エステル化合物U:ジブチルオキサレート(東京化成工業株式会社製、以下、「MSCU」という。)
(57)エステル化合物V:ジエチル−2,2−ジエチル−1,3−プロパンジオアート(和光純薬工業株式会社製、以下、「MSCV」という。別名として、ジエチルジエチルマロネート、とも表現される。)
(58)エステル化合物W:ジエチルシクロヘキサンジカルボキシラート(東京化成工業株式会社製、以下、「MSCW」という。)
(59)エステル化合物X:ジシクロヘキシルオキサレート(Aldrich社製、以下、「MSCX」という。)
(60)エステル化合物Y:ジベンジルオキサレート(Aldrich社製、以下、「MSCY」という。)
(61)エステル化合物Z:ジベンジル−1,3−プロパンジオアート(Aldrich社製、以下、「MSCZ」という。別名として、ジベンジルマロネート、とも表現される。)
(62)エステル化合物AA:ジドデシルオキサレート(Aldrich社製、以下、「MSCAA」という。)
(63)エステル化合物AB:トリエチルメタントリカルボキシレート(Aldrich社製、以下、「MSCAB」という。)
(64)エステル化合物AC:エチルフタリルエチルグリコレート(和光純薬工業株式会社製、以下、「MSCAC」という。)
(65)エステル化合物AD:テトラメチルエタン−1,1−テトラカルボキシラート(和光純薬工業株式会社製、以下、「MSCAD」という。)
(66)エステル化合物AE:アセチルトリエチルシトレート(和光純薬工業株式会社製、以下、「MSCAE」という。)
(67)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。)
(68)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。)
(69)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。)
(70)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。)
(71)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。)
(72)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。)
(73)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。)
(74)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。)
(75)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。)
(76)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。)
(77)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。)
(78)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。)
(79)三ハロゲン化ホウ素化合物Q: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。)
(80)三ハロゲン化ホウ素化合物R: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。)
(81)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。)
(82)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。)
(83)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。)
(84)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。)
(85)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。)
(86)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。)
(87)スルホニウム塩化合物C:商品名「SI−80」(三新化学工業株式会社製、以下、「S80」という。)
(88)スルホニウム塩化合物D:商品名「SI−100」(三新化学工業株式会社製、以下、「S100」という。)
(89)スルホニウム塩化合物E:商品名「SI−110」(三新化学工業株式会社製、以下、「S110」という。)
(90)スルホニウム塩化合物F:商品名「SI−150」(三新化学工業株式会社製、以下、「S150」という。)
(91)スルホニウム塩化合物G:商品名「SI−180」(三新化学工業株式会社製、以下、「S180」という。)
(92)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。)
(93)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。)
(94)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。)
(95)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。)
(96)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。)
(97)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。)
(98)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。)
(99)連鎖移動剤F:エチレンカーボネート(和光純薬工業株式会社製、以下、「CTRF」という。)
(100)連鎖移動剤G:プロピレンカーボネート(Aldrich社製、以下、「CTRG」という。)
(101)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。)
(102)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。)
(103)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。)
<三ハロゲン化ホウ素−エステル化合物の準備>
(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1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−エステル化合物(以下、「BF3−MSCA」という)を準備した。
(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3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5の重合条件に従い重合することで、重合物を得た。
なお、重合条件としては、以下のいずれかを用いた。
・重合条件A
(1)60℃で1時間保持
(2)120℃まで昇温(昇温速度:10℃/hr)
(3)120℃で1時間保持
・重合条件B
(1)60℃で1時間保持
(2)120℃まで昇温(昇温速度:10℃/hr)
(3)120℃で1時間保持
(4)150℃まで昇温(昇温速度:20℃/hr)
(5)150℃で30分間保持
表1〜6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34〜40、53〜56、63〜67では、評価を行うに辺り、重合性評価及び透明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1〜80で調製した組成物の評価結果を表5、6に示す。
表7、8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1〜59の組成物を調製し、表9、10の重合条件に従って、重合物を得た。比較例25〜31、44〜47、54〜58では、評価を行うにあたり、重合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1〜59で調製した組成物の評価結果を表9、10に示す。
<重合物を塗付したガラス基板の準備>
(1)実施例77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86%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80%であったことから、良好と判断した。
(8)光透過性の維持割合(以下、「dTLT」という。)を、下記式を用いて、算出した。
dTLT(%)=TLT300/TLT0×100
(9)光透過性の維持割合が、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、光透過性の維持割合が、93%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80%と良好(「A」)であり、dTLTが93%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11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81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−エステル化合物(BF3−MSCC−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12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−エステル化合物(以下、「BF3−MSCC−2」という)を調製した。
表12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−エステル化合物を調製した。
<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13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15の重合条件に従い重合することで、重合物を得た。
なお、重合条件としては、以下のいずれかを用いた。
・重合条件C
(1)60℃で1時間保持
(2)120℃まで昇温(昇温速度:10℃/hr)
(3)120℃で4時間保持
・重合条件D
(1)60℃で1時間保持
(2)120℃まで昇温(昇温速度:10℃/hr)
(3)120℃で4時間保持
(4)150℃まで昇温(昇温速度:20℃/hr)
(5)150℃で30分間保持
(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150℃として、2000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1%であったことから、特に良好と判断した。
恒温器の器内温度を170℃とした以外は、RA法と同様に行った。
恒温器の器内温度を200℃とした以外は、RA法と同様に行った。
恒温器の器内温度を220℃とした以外は、RA法と同様に行った。
表13、14の組成比率、及び表15、16の重合条件とした以外は、実施例85と同様の方法により、重合物を得た。実施例85〜153で得られた重合物の評価結果を表15、16に示す。
なお、実施例103〜109、116〜124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−エステル化合物(BF3−MSCR−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、ジメチル−1,3−プロパンジオアート32質量%、三フッ化ホウ素ジエチルエーテル錯体68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17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20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(12)により算出した。
指標γ=αd/αep×100 (12)
ここで、
αd:(D)連鎖移動剤の物質量(mol)
αep:(C)エポキシ化合物に含まれるエポキシ基の物質量(mol)、をそれぞれ示す。
(8)上記(7)で得られた重合物のエポキシ基反応率を、表20の方法により測定し、元となるエポキシ化合物中のエポキシ基が重合していることを確認した。
表17〜19の組成比率、及び表20〜22の重合条件とした以外は、実施例154と同様の方法により、重合物を得た。実施例154〜263で得られた重合物の評価結果を表20〜22に示す。
なお、実施例176〜182、189〜204、211〜219では、重合物を封管された耐圧瓶内で用意した。
Claims (12)
- (A)エステル化合物と、(B)三ハロゲン化ホウ素と、(C)エポキシ化合物と、を含有し、前記(A)エステル化合物及び前記(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、組成物。
- 前記(A)エステル化合物が、下記式(1)又は(2)で表される化合物である、請求項1に記載の組成物。
[式中、aは、1以上の数を示し、
R1は、水素原子、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、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く、
R3及びR4は、それぞれ独立に、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置換芳香族炭化水素基を示し、R3及びR4は、互いに連結されていてもよい。] - 前記(A)エステル化合物の炭素数が、3〜26である、請求項1又は2に記載の組成物。
- 前記(A)エステル化合物のエステル基の数が、1〜8である、請求項1〜3のいずれか一項に記載の組成物。
- 下記式(3)で表される、前記(A)エステル化合物と前記(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1〜4のいずれか一項に記載の組成物。
指標α=αs/αb (3)
αs:前記(A)エステル化合物のエステル基の物質量(mol)
αb:前記(B)三ハロゲン化ホウ素の物質量(mol) - 前記(B)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1〜5のいずれか一項に記載の組成物。
- 前記(C)エポキシ化合物が、3員環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1〜6のいずれか一項に記載の組成物。
- 前記(B)三ハロゲン化ホウ素の物質量(mol)と、前記(C)エポキシ化合物に含まれるエポキシ基の物質量(mol)との比が、1:10〜1:100000である、請求項1〜7のいずれか一項に記載の組成物。
- 前記(C)エポキシ化合物のエポキシ当量が、55〜600g/molである、請求項1〜8のいずれか一項に記載の組成物。
- 請求項1〜10のいずれか一項に記載の組成物中の前記(C)エポキシ化合物を重合して形成される、重合物。
- 請求項1〜10のいずれか一項に記載の組成物中の前記(C)エポキシ化合物を加熱及び/又はエネルギー線照射により重合する、重合物の製造方法。
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