JP4632152B2 - 重合性組成物 - Google Patents
重合性組成物 Download PDFInfo
- Publication number
- JP4632152B2 JP4632152B2 JP2004245724A JP2004245724A JP4632152B2 JP 4632152 B2 JP4632152 B2 JP 4632152B2 JP 2004245724 A JP2004245724 A JP 2004245724A JP 2004245724 A JP2004245724 A JP 2004245724A JP 4632152 B2 JP4632152 B2 JP 4632152B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- alkali metal
- metal salt
- epoxy compound
- weak acid
- 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.)
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- 239000000203 mixture Substances 0.000 title claims description 31
- 239000004593 Epoxy Substances 0.000 claims description 66
- -1 alkali metal salt Chemical class 0.000 claims description 65
- 150000001875 compounds Chemical class 0.000 claims description 57
- 229910052783 alkali metal Inorganic materials 0.000 claims description 54
- 239000002253 acid Substances 0.000 claims description 47
- 239000000178 monomer Substances 0.000 claims description 43
- 229920000647 polyepoxide Polymers 0.000 claims description 43
- 125000000962 organic group Chemical group 0.000 claims description 41
- 239000003822 epoxy resin Substances 0.000 claims description 40
- 229920000642 polymer Polymers 0.000 claims description 38
- 239000002585 base Substances 0.000 claims description 30
- 238000010539 anionic addition polymerization reaction Methods 0.000 claims description 22
- 239000003505 polymerization initiator Substances 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 14
- 230000001588 bifunctional effect Effects 0.000 claims description 13
- 229910052700 potassium Inorganic materials 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 229910052708 sodium Inorganic materials 0.000 claims description 7
- 125000005619 boric acid group Chemical group 0.000 claims description 5
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 229910052792 caesium Inorganic materials 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 229910052744 lithium Inorganic materials 0.000 claims description 4
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims description 4
- 229910052701 rubidium Inorganic materials 0.000 claims description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 4
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical group [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 claims description 3
- 125000000129 anionic group Chemical group 0.000 claims description 3
- 125000003700 epoxy group Chemical group 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 15
- 238000006116 polymerization reaction Methods 0.000 description 15
- 150000001450 anions Chemical class 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 150000002500 ions Chemical class 0.000 description 10
- 239000000843 powder Substances 0.000 description 10
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 description 9
- 238000005452 bending Methods 0.000 description 9
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 9
- 229910001414 potassium ion Inorganic materials 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 8
- 238000002156 mixing Methods 0.000 description 8
- 230000000704 physical effect Effects 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 150000002118 epoxides Chemical class 0.000 description 6
- 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 5
- 230000000379 polymerizing effect Effects 0.000 description 5
- 229920001971 elastomer Polymers 0.000 description 4
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 4
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 238000007142 ring opening reaction Methods 0.000 description 4
- 239000004065 semiconductor Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 229920000459 Nitrile rubber Polymers 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- NTXGQCSETZTARF-UHFFFAOYSA-N buta-1,3-diene;prop-2-enenitrile Chemical compound C=CC=C.C=CC#N NTXGQCSETZTARF-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 230000001771 impaired effect Effects 0.000 description 3
- 239000011256 inorganic filler Substances 0.000 description 3
- 229910003475 inorganic filler Inorganic materials 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000012423 maintenance Methods 0.000 description 3
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 3
- 229920001169 thermoplastic Polymers 0.000 description 3
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- 229930185605 Bisphenol Natural products 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 2
- JPYHHZQJCSQRJY-UHFFFAOYSA-N Phloroglucinol Natural products CCC=CCC=CCC=CCC=CCCCCC(=O)C1=C(O)C=C(O)C=C1O JPYHHZQJCSQRJY-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 235000010338 boric acid Nutrition 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 229920005648 ethylene methacrylic acid copolymer Polymers 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000005350 fused silica glass Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000000691 measurement method Methods 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 2
- 229960001553 phloroglucinol Drugs 0.000 description 2
- 235000011007 phosphoric acid Nutrition 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 125000005624 silicic acid group Chemical group 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 239000004416 thermosoftening plastic Substances 0.000 description 2
- 150000003573 thiols Chemical class 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 239000003643 water by type Substances 0.000 description 2
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
- KAKVFSYQVNHFBS-UHFFFAOYSA-N (5-hydroxycyclopenten-1-yl)-phenylmethanone Chemical compound OC1CCC=C1C(=O)C1=CC=CC=C1 KAKVFSYQVNHFBS-UHFFFAOYSA-N 0.000 description 1
- WBODDOZXDKQEFS-UHFFFAOYSA-N 1,2,3,4-tetramethyl-5-phenylbenzene Chemical group CC1=C(C)C(C)=CC(C=2C=CC=CC=2)=C1C WBODDOZXDKQEFS-UHFFFAOYSA-N 0.000 description 1
- OUPZKGBUJRBPGC-UHFFFAOYSA-N 1,3,5-tris(oxiran-2-ylmethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound O=C1N(CC2OC2)C(=O)N(CC2OC2)C(=O)N1CC1CO1 OUPZKGBUJRBPGC-UHFFFAOYSA-N 0.000 description 1
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 1
- MCTWTZJPVLRJOU-UHFFFAOYSA-O 1-methylimidazole Chemical compound CN1C=C[NH+]=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-O 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- AHDSRXYHVZECER-UHFFFAOYSA-N 2,4,6-tris[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(CN(C)C)=C(O)C(CN(C)C)=C1 AHDSRXYHVZECER-UHFFFAOYSA-N 0.000 description 1
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 1
- BBBUAWSVILPJLL-UHFFFAOYSA-N 2-(2-ethylhexoxymethyl)oxirane Chemical compound CCCCC(CC)COCC1CO1 BBBUAWSVILPJLL-UHFFFAOYSA-N 0.000 description 1
- KSJBMDCFYZKAFH-UHFFFAOYSA-N 2-(2-sulfanylethylsulfanyl)ethanethiol Chemical compound SCCSCCS KSJBMDCFYZKAFH-UHFFFAOYSA-N 0.000 description 1
- WAPRZVXVTPSWEB-UHFFFAOYSA-N 2-[(2-butan-2-ylphenoxy)methyl]oxirane Chemical compound CCC(C)C1=CC=CC=C1OCC1OC1 WAPRZVXVTPSWEB-UHFFFAOYSA-N 0.000 description 1
- QDCPNGVVOWVKJG-VAWYXSNFSA-N 2-[(e)-dodec-1-enyl]butanedioic acid Chemical compound CCCCCCCCCC\C=C\C(C(O)=O)CC(O)=O QDCPNGVVOWVKJG-VAWYXSNFSA-N 0.000 description 1
- NQXNYVAALXGLQT-UHFFFAOYSA-N 2-[4-[9-[4-(2-hydroxyethoxy)phenyl]fluoren-9-yl]phenoxy]ethanol Chemical compound C1=CC(OCCO)=CC=C1C1(C=2C=CC(OCCO)=CC=2)C2=CC=CC=C2C2=CC=CC=C21 NQXNYVAALXGLQT-UHFFFAOYSA-N 0.000 description 1
- NKANYVMWDXJHLE-UHFFFAOYSA-N 2-[[2-(oxiran-2-ylmethoxy)phenoxy]methyl]oxirane Chemical compound C1OC1COC1=CC=CC=C1OCC1CO1 NKANYVMWDXJHLE-UHFFFAOYSA-N 0.000 description 1
- BWDQITNIYSXSON-UHFFFAOYSA-N 2-[[3,5-bis(oxiran-2-ylmethoxy)phenoxy]methyl]oxirane Chemical compound C1OC1COC(C=C(OCC1OC1)C=1)=CC=1OCC1CO1 BWDQITNIYSXSON-UHFFFAOYSA-N 0.000 description 1
- AGXAFZNONAXBOS-UHFFFAOYSA-N 2-[[3-(oxiran-2-ylmethyl)phenyl]methyl]oxirane Chemical compound C=1C=CC(CC2OC2)=CC=1CC1CO1 AGXAFZNONAXBOS-UHFFFAOYSA-N 0.000 description 1
- RESFZFUAOCMIOD-UHFFFAOYSA-N 2-[[4-(oxiran-2-ylmethoxy)-2,5-di(propan-2-yl)phenoxy]methyl]oxirane Chemical compound CC(C)C=1C=C(OCC2OC2)C(C(C)C)=CC=1OCC1CO1 RESFZFUAOCMIOD-UHFFFAOYSA-N 0.000 description 1
- FSYPIGPPWAJCJG-UHFFFAOYSA-N 2-[[4-(oxiran-2-ylmethoxy)phenoxy]methyl]oxirane Chemical compound C1OC1COC(C=C1)=CC=C1OCC1CO1 FSYPIGPPWAJCJG-UHFFFAOYSA-N 0.000 description 1
- MEVBAGCIOOTPLF-UHFFFAOYSA-N 2-[[5-(oxiran-2-ylmethoxy)naphthalen-2-yl]oxymethyl]oxirane Chemical compound C1OC1COC(C=C1C=CC=2)=CC=C1C=2OCC1CO1 MEVBAGCIOOTPLF-UHFFFAOYSA-N 0.000 description 1
- LJKDOMVGKKPJBH-UHFFFAOYSA-N 2-ethylhexyl dihydrogen phosphate Chemical compound CCCCC(CC)COP(O)(O)=O LJKDOMVGKKPJBH-UHFFFAOYSA-N 0.000 description 1
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
- WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 1
- WMRCTEPOPAZMMN-UHFFFAOYSA-N 2-undecylpropanedioic acid Chemical compound CCCCCCCCCCCC(C(O)=O)C(O)=O WMRCTEPOPAZMMN-UHFFFAOYSA-N 0.000 description 1
- NZGQHKSLKRFZFL-UHFFFAOYSA-N 4-(4-hydroxyphenoxy)phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=C(O)C=C1 NZGQHKSLKRFZFL-UHFFFAOYSA-N 0.000 description 1
- KLSLBUSXWBJMEC-UHFFFAOYSA-N 4-Propylphenol Chemical compound CCCC1=CC=C(O)C=C1 KLSLBUSXWBJMEC-UHFFFAOYSA-N 0.000 description 1
- KBRQWCWVFNLHPU-UHFFFAOYSA-N 4-[(4-hydroxyphenyl)methyl]-2,3,5,6-tetramethylphenol Chemical compound CC1=C(O)C(C)=C(C)C(CC=2C=CC(O)=CC=2)=C1C KBRQWCWVFNLHPU-UHFFFAOYSA-N 0.000 description 1
- WOCGGVRGNIEDSZ-UHFFFAOYSA-N 4-[2-(4-hydroxy-3-prop-2-enylphenyl)propan-2-yl]-2-prop-2-enylphenol Chemical compound C=1C=C(O)C(CC=C)=CC=1C(C)(C)C1=CC=C(O)C(CC=C)=C1 WOCGGVRGNIEDSZ-UHFFFAOYSA-N 0.000 description 1
- VNGLVZLEUDIDQH-UHFFFAOYSA-N 4-[2-(4-hydroxyphenyl)propan-2-yl]phenol;2-methyloxirane Chemical compound CC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 VNGLVZLEUDIDQH-UHFFFAOYSA-N 0.000 description 1
- WPSWDCBWMRJJED-UHFFFAOYSA-N 4-[2-(4-hydroxyphenyl)propan-2-yl]phenol;oxirane Chemical compound C1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 WPSWDCBWMRJJED-UHFFFAOYSA-N 0.000 description 1
- NUDSREQIJYWLRA-UHFFFAOYSA-N 4-[9-(4-hydroxy-3-methylphenyl)fluoren-9-yl]-2-methylphenol Chemical compound C1=C(O)C(C)=CC(C2(C3=CC=CC=C3C3=CC=CC=C32)C=2C=C(C)C(O)=CC=2)=C1 NUDSREQIJYWLRA-UHFFFAOYSA-N 0.000 description 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- OAOABCKPVCUNKO-UHFFFAOYSA-N 8-methyl Nonanoic acid Chemical compound CC(C)CCCCCCC(O)=O OAOABCKPVCUNKO-UHFFFAOYSA-N 0.000 description 1
- 229910002012 Aerosil® Inorganic materials 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 239000002879 Lewis base Substances 0.000 description 1
- MXRIRQGCELJRSN-UHFFFAOYSA-N O.O.O.[Al] Chemical compound O.O.O.[Al] MXRIRQGCELJRSN-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 229910000410 antimony oxide Inorganic materials 0.000 description 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- JRPRCOLKIYRSNH-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) benzene-1,2-dicarboxylate Chemical compound C=1C=CC=C(C(=O)OCC2OC2)C=1C(=O)OCC1CO1 JRPRCOLKIYRSNH-UHFFFAOYSA-N 0.000 description 1
- XUCHXOAWJMEFLF-UHFFFAOYSA-N bisphenol F diglycidyl ether Chemical compound C1OC1COC(C=C1)=CC=C1CC(C=C1)=CC=C1OCC1CO1 XUCHXOAWJMEFLF-UHFFFAOYSA-N 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
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- 229910052918 calcium silicate Inorganic materials 0.000 description 1
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
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- HJZLEGIHUQOJBA-UHFFFAOYSA-N cyclohexane propionic acid Chemical compound OC(=O)CCC1CCCCC1 HJZLEGIHUQOJBA-UHFFFAOYSA-N 0.000 description 1
- JGNKBMJFNRQMKD-UHFFFAOYSA-N dioctadecoxyborinic acid Chemical compound CCCCCCCCCCCCCCCCCCOB(O)OCCCCCCCCCCCCCCCCCC JGNKBMJFNRQMKD-UHFFFAOYSA-N 0.000 description 1
- WDWQCZSGSFCYTP-UHFFFAOYSA-L dipotassium;2-undecylpropanedioate Chemical compound [K+].[K+].CCCCCCCCCCCC(C([O-])=O)C([O-])=O WDWQCZSGSFCYTP-UHFFFAOYSA-L 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
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- 239000003480 eluent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- FPIQZBQZKBKLEI-UHFFFAOYSA-N ethyl 1-[[2-chloroethyl(nitroso)carbamoyl]amino]cyclohexane-1-carboxylate Chemical compound ClCCN(N=O)C(=O)NC1(C(=O)OCC)CCCCC1 FPIQZBQZKBKLEI-UHFFFAOYSA-N 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 229920006015 heat resistant resin Polymers 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- CUUJVBDPSUOTIQ-UHFFFAOYSA-N hydroxy-dimethyl-octadecylsilane Chemical compound CCCCCCCCCCCCCCCCCC[Si](C)(C)O CUUJVBDPSUOTIQ-UHFFFAOYSA-N 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 150000007527 lewis bases Chemical class 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 1
- VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical compound [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 238000011417 postcuring Methods 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 229940114930 potassium stearate Drugs 0.000 description 1
- JAGSXRDUCWAZFH-UHFFFAOYSA-M potassium;3-cyclohexylpropanoate Chemical compound [K+].[O-]C(=O)CCC1CCCCC1 JAGSXRDUCWAZFH-UHFFFAOYSA-M 0.000 description 1
- VFLADTURPGNKHV-UHFFFAOYSA-M potassium;cyclohexanecarboxylate Chemical compound [K+].[O-]C(=O)C1CCCCC1 VFLADTURPGNKHV-UHFFFAOYSA-M 0.000 description 1
- ANBFRLKBEIFNQU-UHFFFAOYSA-M potassium;octadecanoate Chemical compound [K+].CCCCCCCCCCCCCCCCCC([O-])=O ANBFRLKBEIFNQU-UHFFFAOYSA-M 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 239000012779 reinforcing material Substances 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 230000008685 targeting Effects 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
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- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
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- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/42—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
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Description
従って、本発明は、エポキシ化合物と前記エポキシ化合物をアニオン重合させるためのアニオン重合開始剤とからなり、前記重合開始剤は有機基を有する弱酸モノマーのアルカリ金属塩からなることを特徴とするアニオン重合性エポキシ化合物組成物である。
本発明の他の一態様において、上記有機基を有する弱酸モノマーのアルカリ金属塩は、Li、Na、K、Rb及びCsからなる群から選択される少なくとも1種のアルカリ金属の塩、とくに、Na又はKの塩である。
本発明の他の態様において、上記エポキシ化合物は、1官能エポキシ化合物又はグリシジルオキシ基、グリシジルアミノ基及び3,4−エポキシシクロヘキセニル基からなる群から選択される少なくとも1種を有する2官能以上のエポキシ樹脂である。
(1)有機基を有する弱酸モノマーのアルカリ金属塩を用いてエポキシ化合物を重合させることができる。
(2)高い反応速度で重合体を生成する。
(3)停止反応、連鎖移動が起こりにくく、エポキシ化合物の高い重合度を実現する。
(4)アニオン重合開始剤の製造が容易である。
(5)硬化物の樹脂強度、靱性が高い。
(6)1官能エポキシ化合物の高い重合度の重合体を製造することができる。
(7)1官能エポキシ化合物を重合することにより、線型で長い重合体が形成され、熱可塑性ポリマーを製造することができる。
(8)本発明のアニオン重合開始剤は、吸湿性が比較的低く、空気中で作業することが可能である。
(9)2官能以上のエポキシ化合物を重合することにより、損失正接の極大値として観測しうるTgを事実上持たない高耐熱性樹脂を製造することができる。
以下、本発明を詳細に説明する。
EX146:p−t−ブチルフェノールグリシジルエーテル(1官能、エポキシ当量=205g/eq)ナガセケムテックス社製
AER260: ビスフェノールA型エポキシ樹脂(2官能、エポキシ当量=190g/eq)旭化成社製
フロログルシノールPGE: フロログルシノールトリグリシジルエーテル(3官能、エポキシ当量=117g/eq)ナガセケムテックス社製
CTBN1008SPK: CTBN1008SP(カルボン酸末端ブタジエン−アクリロニトリル・液状ゴム、2官能、宇部興産社製)のカリウム塩(カリウムイオン当量=1887g/eq)
CTBN1009SPK: CTBN1009SP(カルボン酸末端ブタジエン−アクリロニトリル・液状ゴム、3官能、宇部興産製)のカリウム塩(カリウムイオン当量=1590g/eq)
ACK: 酢酸カリウム(カリウムイオン当量=98g/eq)
CHPK: 3−シクロヘキシルプロピオン酸カリウム(カリウムイオン当量=184g/eq)
CPK: n−カプリル酸カリウム(カリウムイオン当量=182g/eq)
CHK: シクロヘキサンカルボン酸カリウム(カリウムイオン当量=166g/eq)
LK: ラウリル酸カリウム(カリウムイオン当量=225g/eq)
STK: ステアリン酸カリウム(カリウムイオン当量=332g/eq)
DDK: ドデカンジカルボン酸ジカリウム(カリウムイオン当量=103g/eq)
EHC−30: アデカハードナーEHC−30、2,4,6−トリスジメチルアミノメチルフェノール、旭電化工業社製
1MZ: 1−メチルイミダゾール、BASF社製
IK: エチレン−メタクリル酸共重合体のカリウム塩、(カリウムイオン当量=464g/eq)三井・デュポン社製
RY200S: フュームドシリカ、日本アエロジル社製
実施例1〜6及び比較例1〜4
エポキシドとしてEX146を用い、表1に示すアニオン重合開始剤及び配合量で配合した。3本ロールを用いて均一な組成物を調製し、180℃で反応を開始させた後、表に示す時間の経過後に反応物をGPCにかけて、反応物の分子量分布を調べた。結果を表1〜3に示した。また、実施例2のGPCチャートを図1に示した。
なお、GPCの条件は以下のとおり。
日本ウォーターズ社製GPC Alliance/Empowerシステムを用い、検出器に2414示差屈折計(日本ウォーターズ社製)を用いて測定した。カラムは、Shodex KF−802、KF−803、KF−805(昭和電工社製)を直列につないで使用した。溶出液はTHFを使用し、カラム温度40℃で流速1ml/分とした。
実施例1〜6から、モノエポキシドのポリマーが溶剤可溶性であり、架橋構造を持たないことが確かめられた。
実施例7〜15及び比較例5〜7
表4に示す成分及び配合量を用いて配合した。混合して均一な組成物を調製し、120℃/2時間の硬化及び180℃/4時間の後硬化の硬化条件で硬化物を得た。長さ約20mm、幅約10〜15mm、厚さ約2mmのサンプルについて、以下の方法で曲げ弾性率E′及び動的粘弾性における損失正接(tanδ)を求めた。25℃における曲げ弾性率と250℃における曲げ弾性率の値から、弾性率維持率を求めた。弾性率維持率は以下の式による。
弾性率維持率=(250℃における曲げ弾性率の値/25℃における曲げ弾性率の値)×100(%)
ただし、比較例6は250℃ではなく190℃でのデータを使用した。
また、0〜300℃の範囲でtanδの最大値をチャートから読み取った。結果を表4に示した。また、典型例として、図2に実施例11のtanδチャートを、図3に比較例5のtanδチャートを示した。
曲げ弾性率及び動的粘弾性における損失正接tanδ
セイコーインスツルメント社製粘弾性測定装置DMS6100を用いて、両持ち曲げモードで1Hzの正弦歪みを印加することにより測定した。測定温度範囲は0〜300℃で、昇温速度は2℃/minとした。
測定方法
曲げ強度(MPa):ASTM D790に準拠(クロスヘッドスピード2mm/分)
破壊靱性値(MPa・m1/2):ASTM D5045に準拠したコンパクトテンション法による(クロスヘッドスピード1mm/分)
いずれも、万能試験機インスロン(インスロン社製)を使用して測定した。結果を表5に示した。
Claims (14)
- エポキシ化合物と前記エポキシ化合物をアニオン重合させるためのアニオン重合開始剤とからなり、前記重合開始剤は有機基を有する弱酸モノマーのアルカリ金属塩からなることを特徴とするアニオン重合性エポキシ化合物組成物。
- 前記有機基を有する弱酸モノマーのアルカリ金属塩は、有機基を有する1官能の弱酸モノマーのアルカリ金属塩である請求項1記載の組成物。
- 前記有機基を有する弱酸モノマーのアルカリ金属塩は、共役塩基としてカルボン酸基の共役塩基、リン酸基の共役塩基、ホウ酸基の共役塩基、ケイ酸基の共役塩基、チオール基の共役塩基及びフェノール性水酸基の共役塩基からなる群から選択される少なくとも1種を含有するものである請求項1又は2記載の組成物。
- 前記有機基を有する弱酸モノマーのアルカリ金属塩は、Li、Na、K、Rb及びCsからなる群から選択される少なくとも1種のアルカリ金属の塩である請求項1〜3のいずれか記載の組成物。
- 前記有機基を有する弱酸モノマーのアルカリ金属塩は、Na又はKの塩である請求項4記載の組成物。
- 前記エポキシ化合物は、1官能エポキシ化合物である請求項1〜5のいずれか記載の組成物。
- 前記エポキシ化合物は、グリシジルオキシ基、グリシジルアミノ基及び3,4−エポキシシクロヘキセニル基からなる群から選択される少なくとも1種を有する2官能以上のエポキシ樹脂である請求項1〜5のいずれか記載の組成物。
- エポキシ化合物を、有機基を有する弱酸モノマーのアルカリ金属塩をアニオン重合開始剤として用いてアニオン重合させることを特徴とするエポキシ化合物重合体の製造方法。
- 前記有機基を有する弱酸モノマーのアルカリ金属塩は、有機基を有する1官能の弱酸モノマーのアルカリ金属塩である請求項8記載の製造方法。
- 前記エポキシ化合物は、1官能エポキシ化合物である請求項8又は9記載の製造方法。
- 前記エポキシ化合物は、2官能以上のエポキシ樹脂である請求項8又は9記載の製造方法。
- 前記有機基を有する弱酸モノマーのアルカリ金属塩は、共役塩基としてカルボン酸基の共役塩基、リン酸基の共役塩基、ホウ酸基の共役塩基、ケイ酸基の共役塩基、チオール基の共役塩基及びフェノール性水酸基の共役塩基からなる群から選択される少なくとも1種を含有するものである請求項8〜11のいずれか記載の製造方法。
- 前記有機基を有する弱酸モノマーのアルカリ金属塩は、Li、Na、K、Rb及びCsからなる群から選択される少なくとも1種のアルカリ金属の塩である請求項8〜12のいずれか記載の製造方法。
- 前記有機基を有する弱酸モノマーのアルカリ金属塩は、Na又はKの塩である請求項13記載の製造方法。
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US4186086A (en) * | 1978-06-26 | 1980-01-29 | The Dow Chemical Company | Weak base ion exchange resins of a polyalkylenepolyamine and polyepoxide |
US4485221A (en) * | 1983-11-03 | 1984-11-27 | Ciba-Geigy Corporation | Process for making epoxy novolac resins with low hydrolyzable chlorine and low ionic chloride content |
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- 2004-08-25 JP JP2004245724A patent/JP4632152B2/ja active Active
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- 2005-08-24 EP EP05780890A patent/EP1795549A4/en not_active Withdrawn
- 2005-08-24 US US11/661,208 patent/US8809470B2/en not_active Expired - Fee Related
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JP2002220454A (ja) * | 2000-11-22 | 2002-08-09 | Toray Ind Inc | ポリエステル組成物およびコネクター |
Also Published As
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US20080139758A1 (en) | 2008-06-12 |
EP1795549A4 (en) | 2008-11-05 |
JP2006063154A (ja) | 2006-03-09 |
EP1795549A1 (en) | 2007-06-13 |
US8809470B2 (en) | 2014-08-19 |
WO2006022278A1 (ja) | 2006-03-02 |
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