JP2018158969A - 硬化剤組成物、樹脂組成物および樹脂硬化物 - Google Patents
硬化剤組成物、樹脂組成物および樹脂硬化物 Download PDFInfo
- Publication number
- JP2018158969A JP2018158969A JP2017055769A JP2017055769A JP2018158969A JP 2018158969 A JP2018158969 A JP 2018158969A JP 2017055769 A JP2017055769 A JP 2017055769A JP 2017055769 A JP2017055769 A JP 2017055769A JP 2018158969 A JP2018158969 A JP 2018158969A
- Authority
- JP
- Japan
- Prior art keywords
- resin
- curing agent
- curing
- weight
- composition
- 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
- 229920005989 resin Polymers 0.000 title claims abstract description 63
- 239000011347 resin Substances 0.000 title claims abstract description 63
- 239000011342 resin composition Substances 0.000 title claims abstract description 46
- 239000000203 mixture Substances 0.000 title claims abstract description 31
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 57
- 229920001567 vinyl ester resin Polymers 0.000 claims abstract description 35
- 239000000178 monomer Substances 0.000 claims abstract description 33
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 claims abstract description 12
- -1 t-hexyl peroxyisopropyl carbonate Chemical compound 0.000 claims description 21
- 229910052751 metal Inorganic materials 0.000 claims description 9
- 239000002184 metal Substances 0.000 claims description 9
- 230000001133 acceleration Effects 0.000 claims description 6
- 229920000049 Carbon (fiber) Polymers 0.000 claims description 5
- 239000004917 carbon fiber Substances 0.000 claims description 5
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 4
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 claims description 3
- 238000005187 foaming Methods 0.000 abstract description 11
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 abstract description 3
- IBONIHUTBISJPX-UHFFFAOYSA-N 2-methylbutan-2-ylperoxy propan-2-yl carbonate Chemical compound CCC(C)(C)OOOC(=O)OC(C)C IBONIHUTBISJPX-UHFFFAOYSA-N 0.000 abstract 1
- GOYXMRDQMFXZRP-UHFFFAOYSA-N 2-methylpentan-2-ylperoxy propan-2-yl carbonate Chemical compound CCCC(C)(C)OOOC(=O)OC(C)C GOYXMRDQMFXZRP-UHFFFAOYSA-N 0.000 abstract 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical group C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 19
- 238000000034 method Methods 0.000 description 18
- 239000000047 product Substances 0.000 description 17
- 238000000465 moulding Methods 0.000 description 10
- 238000011156 evaluation Methods 0.000 description 9
- 239000012855 volatile organic compound Substances 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 7
- 229910017052 cobalt Inorganic materials 0.000 description 6
- 239000010941 cobalt Substances 0.000 description 6
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 150000001451 organic peroxides Chemical class 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 239000012744 reinforcing agent Substances 0.000 description 5
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 4
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 4
- 239000003677 Sheet moulding compound Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 4
- 239000003822 epoxy resin Substances 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 4
- 229920000647 polyepoxide Polymers 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 3
- 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 3
- 229910052742 iron Inorganic materials 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- IEMBFTKNPXENSE-UHFFFAOYSA-N 2-(2-methylpentan-2-ylperoxy)propan-2-yl hydrogen carbonate Chemical compound CCCC(C)(C)OOC(C)(C)OC(O)=O IEMBFTKNPXENSE-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 description 2
- FEHUHAVQGZZDMW-UHFFFAOYSA-N 5-methyl-4-piperidin-1-yl-2-propan-2-ylphenol Chemical compound C1=C(O)C(C(C)C)=CC(N2CCCCC2)=C1C FEHUHAVQGZZDMW-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 2
- 239000004918 carbon fiber reinforced polymer Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000009787 hand lay-up Methods 0.000 description 2
- 238000001746 injection moulding Methods 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 2
- 229920003986 novolac Polymers 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000001721 transfer moulding Methods 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- QEQBMZQFDDDTPN-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy benzenecarboperoxoate Chemical group CC(C)(C)OOOC(=O)C1=CC=CC=C1 QEQBMZQFDDDTPN-UHFFFAOYSA-N 0.000 description 1
- KDGNCLDCOVTOCS-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy propan-2-yl carbonate Chemical compound CC(C)OC(=O)OOC(C)(C)C KDGNCLDCOVTOCS-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 1
- CISIJYCKDJSTMX-UHFFFAOYSA-N 2,2-dichloroethenylbenzene Chemical compound ClC(Cl)=CC1=CC=CC=C1 CISIJYCKDJSTMX-UHFFFAOYSA-N 0.000 description 1
- SPSPIUSUWPLVKD-UHFFFAOYSA-N 2,3-dibutyl-6-methylphenol Chemical compound CCCCC1=CC=C(C)C(O)=C1CCCC SPSPIUSUWPLVKD-UHFFFAOYSA-N 0.000 description 1
- BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 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
- UIERETOOQGIECD-ARJAWSKDSA-M 2-Methyl-2-butenoic acid Natural products C\C=C(\C)C([O-])=O UIERETOOQGIECD-ARJAWSKDSA-M 0.000 description 1
- MQFDMZNZEHTLND-UHFFFAOYSA-N 2-[(2-methylpropan-2-yl)oxy]benzoic acid Chemical compound CC(C)(C)OC1=CC=CC=C1C(O)=O MQFDMZNZEHTLND-UHFFFAOYSA-N 0.000 description 1
- SBYMUDUGTIKLCR-UHFFFAOYSA-N 2-chloroethenylbenzene Chemical compound ClC=CC1=CC=CC=C1 SBYMUDUGTIKLCR-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- DXIJHCSGLOHNES-UHFFFAOYSA-N 3,3-dimethylbut-1-enylbenzene Chemical compound CC(C)(C)C=CC1=CC=CC=C1 DXIJHCSGLOHNES-UHFFFAOYSA-N 0.000 description 1
- CWPKTBMRVATCBL-UHFFFAOYSA-N 3-[1-[1-[(2-methylphenyl)methyl]piperidin-4-yl]piperidin-4-yl]-1h-benzimidazol-2-one Chemical compound CC1=CC=CC=C1CN1CCC(N2CCC(CC2)N2C(NC3=CC=CC=C32)=O)CC1 CWPKTBMRVATCBL-UHFFFAOYSA-N 0.000 description 1
- 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 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 229910002012 Aerosil® Inorganic materials 0.000 description 1
- UIERETOOQGIECD-UHFFFAOYSA-N Angelic acid Natural products CC=C(C)C(O)=O UIERETOOQGIECD-UHFFFAOYSA-N 0.000 description 1
- RINWGRJHXCCLOV-UHFFFAOYSA-N BPO Chemical compound BPO RINWGRJHXCCLOV-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- 229920002799 BoPET Polymers 0.000 description 1
- REIYHFWZISXFKU-UHFFFAOYSA-N Butyl acetoacetate Chemical compound CCCCOC(=O)CC(C)=O REIYHFWZISXFKU-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 101500028161 Homo sapiens Tumor necrosis factor-binding protein 1 Proteins 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 102100029290 Transthyretin Human genes 0.000 description 1
- 108050000089 Transthyretin Proteins 0.000 description 1
- 102400000089 Tumor necrosis factor-binding protein 1 Human genes 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000004760 aramid Substances 0.000 description 1
- 229920006231 aramid fiber Polymers 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000009730 filament winding Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 238000010813 internal standard method Methods 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- SGGOJYZMTYGPCH-UHFFFAOYSA-L manganese(2+);naphthalene-2-carboxylate Chemical compound [Mn+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 SGGOJYZMTYGPCH-UHFFFAOYSA-L 0.000 description 1
- SGLXWMAOOWXVAM-UHFFFAOYSA-L manganese(2+);octanoate Chemical compound [Mn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O SGLXWMAOOWXVAM-UHFFFAOYSA-L 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 150000002976 peresters Chemical class 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- DHGFMVMDBNLMKT-UHFFFAOYSA-N propyl 3-oxobutanoate Chemical compound CCCOC(=O)CC(C)=O DHGFMVMDBNLMKT-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- PFBLRDXPNUJYJM-UHFFFAOYSA-N tert-butyl 2-methylpropaneperoxoate Chemical compound CC(C)C(=O)OOC(C)(C)C PFBLRDXPNUJYJM-UHFFFAOYSA-N 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- UIERETOOQGIECD-ONEGZZNKSA-N tiglic acid Chemical compound C\C=C(/C)C(O)=O UIERETOOQGIECD-ONEGZZNKSA-N 0.000 description 1
- UAXOELSVPTZZQG-UHFFFAOYSA-N tiglic acid Natural products CC(C)=C(C)C(O)=O UAXOELSVPTZZQG-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Landscapes
- Macromonomer-Based Addition Polymer (AREA)
Abstract
Description
本発明の硬化剤は、有機過酸化物であり、少なくとも、(a)クメンハイドロパーオキサイドと、(b)t−ヘキシルパーオキシイソプロピルカーボネートおよび/またはt−アミルパーオキシイソプロピルカーボネートである。
本発明の硬化促進助剤は、(c)アセト酢酸エステルである。前記(c)アセト酢酸エステルとしては、例えば、アセト酢酸メチル、アセト酢酸エチル、アセト酢酸プロピル、アセト酢酸ブチルなどが挙げられ、アセト酢酸メチル、アセト酢酸エチルが好ましい。(c)アセト酢酸エステルは、単独で使用してもよく、2種以上を組み合わせて使用してもよい。
本発明のビニルエステル樹脂は、エポキシ樹脂と、α,β−不飽和モノカルボン酸とを公知の方法によりビニルエステル樹脂化させることで得られるエポキシ(メタ)アクリレートである。
本発明のラジカル重合性モノマーは、モノマー成分として、スチレンモノマーを含むことが好ましい。さらに、スチレンモノマーのほかに、他のラジカル重合性モノマーを含有してもよい。
<硬化剤組成物の製造>
ポリエチレン容器に、硬化剤として(a)クメンハイドロパーオキサイド(以下、CHPとも称す)20重量部、および(b)t−ヘキシルパーオキシイソプロピルカーボネート(以下、THPIとも称す)80重量部と、硬化促進助剤として(c)アセト酢酸メチル50重量部を加えて混合し、実施例1の硬化剤組成物を製造した。なお、硬化剤に使用した各商品には、有機過酸化物のほかに、希釈剤等を含有するが、上記の硬化剤の配合量は、有機過酸化物の配合量に相当する。
実施例1において、硬化剤組成物の調製に用いた硬化剤と硬化促進助剤、それらの配合量を表1に示すように変えたこと以外は、実施例1と同様の操作を行い、硬化剤組成物を製造した。
<樹脂組成物の製造>
ポリエチレン容器に、ビニルエステル樹脂と、ラジカル重合性モノマーとしてスチレンモノマーを含有する樹脂混合物(商品名:リポキシR−802、昭和電工社製、ビニルエステル樹脂濃度:50重量%、スチレンモノマー濃度:50重量%)100重量部に、金属系硬化促進剤としてナフテン酸コバルト(6重量%溶液)0.5重量部を加え混合した。次いで、得られた混合組成物に、上記の実施例1の硬化剤組成物1.5重量部を加え混合し、実施例1−1の樹脂組成物を製造した。
実施例1−1において、硬化剤組成物の種類とその配合量を表2または表3に示すように変えたこと以外は、実施例1−1と同様の操作を行い、樹脂組成物を製造した。
樹脂組成物の発泡の評価は、上記の実施例および比較例の樹脂組成物の製造において、製造直後の樹脂組成物の発泡の有無を目視にて観察した。
硬化剤組成物の硬化特性の測定は、上記で得られた実施例および比較例の硬化剤組成物を用い、JIS K6901:2008の常温硬化特性(発熱法)の試験法に準じて25℃における硬化試験を行い、以下のように特性値を求めた。
ゲル化時間(GT):試験開始から試験温度プラス5℃に要する時間(分)
硬化時間(CT):試験開始からPETに要する時間(分)
最高発熱温度(PET)(℃)
樹脂硬化物のスチレンモノマーの残存量の評価は、上方に空気が抜けるように隙間の空いたシリコーンゴム製スペーサーで作製した型枠を、PETフィルムを貼付したガラス板2枚で挟み、上記で得られた実施例および比較例の樹脂組成物を、樹脂硬化物の大きさが縦50mm×横100mm、厚みが5mmもしくは3mmになるように流し込み、空気循環式乾燥機内に、以下の所定の条件((a)または(b))にて、放置することで注型板状の樹脂硬化物を得た。
(a):温度25℃、1週間放置
(b):上記(a)で放置した後、さらに、温度80℃、2時間放置
樹脂硬化物の外観の評価は、上記の条件(a)で得られた厚み3mmの樹脂硬化物の外観について、クラックの有無を目視にて評価した。
樹脂硬化の硬化度の評価は、上記の条件(b)で得られた厚み3mmの樹脂硬化物の硬度を測定することにより行った。硬度は、バーバーコールマン製のバーコール硬度計GYZJ934−1で測定した。
THPIは、t−ヘキシルパーオキシイソプロピルカーボネート(商品名:パーヘキシルI、日油社製);
TAPIは、t−アミルパーオキシイソプロピルカーボネート(商品名:パーアミルI、日油社製)
TBPBは、t−ブチルパーオキシベンゾエート(商品名:パーブチルZ、日油社製)
TBPAは、t−ブチルパーオキシアセテート(商品名:パーブチルA、日油社製)
TBPIは、t−ブチルパーオキシイソプロピルカーボネート(商品名:パーブチルI、日油社製)
Claims (5)
- 硬化剤および硬化促進助剤を含む硬化剤組成物であって、
前記硬化剤は、(a)クメンハイドロパーオキサイドと、(b)t−ヘキシルパーオキシイソプロピルカーボネートおよび/またはt−アミルパーオキシイソプロピルカーボネートであり、
前記硬化促進助剤は、(c)アセト酢酸エステルであり、
前記(a)と前記(b)の合計100重量部において、前記(a)が8〜60重量部であり、
前記(a)と前記(b)の合計100重量部に対して、前記(c)が30〜70重量部であることを特徴とするビニルエステル樹脂用の硬化剤組成物。 - 請求項1記載の硬化剤組成物と、ビニルエステル樹脂と、ラジカル重合性モノマーと、金属系硬化促進剤を含有することを特徴とする樹脂組成物。
- 前記ビニルエステル樹脂と前記ラジカル重合性モノマーの合計100重量部に対して、前記硬化剤組成物が0.2〜8重量部であることを特徴とする請求項2記載の樹脂組成物。
- 請求項2または3記載の樹脂組成物から得られることを特徴とする樹脂硬化物。
- 炭素繊維強化樹脂に用いられることを特徴とする請求項2または3記載の樹脂組成物。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2017055769A JP6845472B2 (ja) | 2017-03-22 | 2017-03-22 | 硬化剤組成物、樹脂組成物および樹脂硬化物 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2017055769A JP6845472B2 (ja) | 2017-03-22 | 2017-03-22 | 硬化剤組成物、樹脂組成物および樹脂硬化物 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2018158969A true JP2018158969A (ja) | 2018-10-11 |
JP6845472B2 JP6845472B2 (ja) | 2021-03-17 |
Family
ID=63795456
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2017055769A Active JP6845472B2 (ja) | 2017-03-22 | 2017-03-22 | 硬化剤組成物、樹脂組成物および樹脂硬化物 |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP6845472B2 (ja) |
-
2017
- 2017-03-22 JP JP2017055769A patent/JP6845472B2/ja active Active
Also Published As
Publication number | Publication date |
---|---|
JP6845472B2 (ja) | 2021-03-17 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP4888027B2 (ja) | ラジカル重合型熱硬化性樹脂用硬化剤、それを含む成形材料及びその硬化方法 | |
CA1089143A (en) | Radiation curable epoxy ester resin containing a vinyl polymer | |
KR20190068552A (ko) | 섬유 강화 복합 재료용 수지 조성물 및 그것을 이용한 섬유 강화 복합 재료 | |
JP6845472B2 (ja) | 硬化剤組成物、樹脂組成物および樹脂硬化物 | |
JP6853499B2 (ja) | 硬化剤組成物、樹脂組成物および樹脂硬化物 | |
JP6880493B2 (ja) | 硬化剤組成物、樹脂組成物および樹脂硬化物 | |
JP2010150352A (ja) | ラジカル重合型熱硬化性樹脂用硬化剤及びそれを含む成形材料 | |
JPH11209446A (ja) | 不飽和ポリエステル樹脂又はビニルエステル樹脂用硬化剤組成物及び不飽和ポリエステル樹脂又はビニルエステル樹脂の硬化物の製造方法 | |
JP2019085476A (ja) | ビニルエステル樹脂組成物、複合材料及び硬化物 | |
JP2021091805A (ja) | 熱硬化性樹脂組成物 | |
JP5240006B2 (ja) | 成形材料の硬化方法 | |
CN112805310B (zh) | 乙烯基酯树脂组合物、包含该组合物的复合材料及该组合物或复合材料的固化物 | |
JP7496690B2 (ja) | 水含有硬化性組成物、繊維強化硬化性材料、ライニング材およびライニング施工体 | |
JP2001139615A (ja) | 有機過酸化物組成物及びその用途 | |
JP3906122B2 (ja) | 貯蔵安定性に優れた人造大理石用ビニルエステル樹脂組成物 | |
JP2851414B2 (ja) | 耐熱性ビニルエステル樹脂組成物 | |
JP2019500451A (ja) | 液体プレポリマー組成物のペルオキシエステル硬化 | |
JP2001002718A (ja) | 硬化剤組成物、これを用いる硬化方法及び硬化物 | |
JP2019108435A (ja) | ビニルエステル樹脂組成物、複合材料及び硬化物 | |
JP2022153921A (ja) | ビニルエステル樹脂組成物およびその樹脂成形体 | |
JP3793606B2 (ja) | パーオキサイド及びこれを含有する樹脂組成物、成形材料 | |
JP2024080764A (ja) | ラジカル重合性樹脂組成物 | |
JP2006265284A (ja) | 着色硬化剤組成物、ラジカル重合型熱硬化性樹脂の硬化方法、及び硬化物 | |
EP0106655A2 (en) | Modified unsaturated polyester resins | |
CN112638969A (zh) | 乙烯基酯树脂组合物、包含该组合物的复合材料、和该组合物或复合材料的固化物 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20200210 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20200716 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20201111 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20201120 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20210127 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20210209 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 6845472 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |