WO2023157750A1 - Resin composition for fiber-reinforced plastic, and fiber-reinforced plastic - Google Patents
Resin composition for fiber-reinforced plastic, and fiber-reinforced plastic Download PDFInfo
- Publication number
- WO2023157750A1 WO2023157750A1 PCT/JP2023/004329 JP2023004329W WO2023157750A1 WO 2023157750 A1 WO2023157750 A1 WO 2023157750A1 JP 2023004329 W JP2023004329 W JP 2023004329W WO 2023157750 A1 WO2023157750 A1 WO 2023157750A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- fiber
- resin composition
- component
- reinforced plastics
- reinforced plastic
- Prior art date
Links
- 229920002430 Fibre-reinforced plastic Polymers 0.000 title claims abstract description 44
- 239000011151 fibre-reinforced plastic Substances 0.000 title claims abstract description 44
- 239000011342 resin composition Substances 0.000 title claims abstract description 40
- 239000003822 epoxy resin Substances 0.000 claims abstract description 31
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 31
- 229920000768 polyamine Polymers 0.000 claims abstract description 19
- 150000001875 compounds Chemical class 0.000 claims abstract description 16
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 4
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 4
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 2
- -1 polyoxypropylene Polymers 0.000 claims description 32
- 239000000203 mixture Substances 0.000 claims description 8
- 239000006087 Silane Coupling Agent Substances 0.000 claims description 7
- 239000003085 diluting agent Substances 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000012783 reinforcing fiber Substances 0.000 claims description 4
- 229920001451 polypropylene glycol Polymers 0.000 claims description 3
- 238000004040 coloring Methods 0.000 abstract description 10
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 18
- 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 16
- 229920005989 resin Polymers 0.000 description 11
- 239000011347 resin Substances 0.000 description 11
- 239000004593 Epoxy Substances 0.000 description 10
- 239000000835 fiber Substances 0.000 description 10
- 238000000465 moulding Methods 0.000 description 9
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 9
- 229910052719 titanium Inorganic materials 0.000 description 9
- 239000010936 titanium Substances 0.000 description 9
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 9
- 239000000463 material Substances 0.000 description 8
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 229910052726 zirconium Inorganic materials 0.000 description 7
- 229920003986 novolac Polymers 0.000 description 6
- 230000000704 physical effect Effects 0.000 description 6
- 229930185605 Bisphenol Natural products 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000003365 glass fiber Substances 0.000 description 5
- HHRACYLRBOUBKM-UHFFFAOYSA-N 2-[(4-tert-butylphenoxy)methyl]oxirane Chemical compound C1=CC(C(C)(C)C)=CC=C1OCC1OC1 HHRACYLRBOUBKM-UHFFFAOYSA-N 0.000 description 4
- 239000004743 Polypropylene Substances 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 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 4
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical group C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 229920001155 polypropylene Polymers 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 229920000049 Carbon (fiber) Polymers 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000004917 carbon fiber Substances 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- LYMYULOYDUWMOP-UHFFFAOYSA-M diethoxy-sulfanylidene-sulfido-$l^{5}-phosphane;tetrabutylphosphanium Chemical compound CCOP([S-])(=S)OCC.CCCC[P+](CCCC)(CCCC)CCCC LYMYULOYDUWMOP-UHFFFAOYSA-M 0.000 description 3
- 125000003700 epoxy group Chemical group 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 239000002657 fibrous material Substances 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 2
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 2
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- UMHKOAYRTRADAT-UHFFFAOYSA-N [hydroxy(octoxy)phosphoryl] octyl hydrogen phosphate Chemical compound CCCCCCCCOP(O)(=O)OP(O)(=O)OCCCCCCCC UMHKOAYRTRADAT-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000007822 coupling agent Substances 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical class CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- IXQGCWUGDFDQMF-UHFFFAOYSA-N o-Hydroxyethylbenzene Natural products CCC1=CC=CC=C1O IXQGCWUGDFDQMF-UHFFFAOYSA-N 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- QBDSZLJBMIMQRS-UHFFFAOYSA-N p-Cumylphenol Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=CC=C1 QBDSZLJBMIMQRS-UHFFFAOYSA-N 0.000 description 2
- 150000002989 phenols Chemical class 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
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- 230000002787 reinforcement Effects 0.000 description 2
- 239000012779 reinforcing material Substances 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 238000001721 transfer moulding Methods 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- 239000002759 woven fabric Substances 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- NIDNOXCRFUCAKQ-UMRXKNAASA-N (1s,2r,3s,4r)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid Chemical compound C1[C@H]2C=C[C@@H]1[C@H](C(=O)O)[C@@H]2C(O)=O NIDNOXCRFUCAKQ-UMRXKNAASA-N 0.000 description 1
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- CFQZKFWQLAHGSL-FNTYJUCDSA-N (3e,5e,7e,9e,11e,13e,15e,17e)-18-[(3e,5e,7e,9e,11e,13e,15e,17e)-18-[(3e,5e,7e,9e,11e,13e,15e)-octadeca-3,5,7,9,11,13,15,17-octaenoyl]oxyoctadeca-3,5,7,9,11,13,15,17-octaenoyl]oxyoctadeca-3,5,7,9,11,13,15,17-octaenoic acid Chemical compound OC(=O)C\C=C\C=C\C=C\C=C\C=C\C=C\C=C\C=C\OC(=O)C\C=C\C=C\C=C\C=C\C=C\C=C\C=C\C=C\OC(=O)C\C=C\C=C\C=C\C=C\C=C\C=C\C=C\C=C CFQZKFWQLAHGSL-FNTYJUCDSA-N 0.000 description 1
- YOBOXHGSEJBUPB-MTOQALJVSA-N (z)-4-hydroxypent-3-en-2-one;zirconium Chemical compound [Zr].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O YOBOXHGSEJBUPB-MTOQALJVSA-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
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- HIQAWCBKWSQMRQ-UHFFFAOYSA-N 16-methylheptadecanoic acid;2-methylprop-2-enoic acid;propan-2-ol;titanium Chemical compound [Ti].CC(C)O.CC(=C)C(O)=O.CC(=C)C(O)=O.CC(C)CCCCCCCCCCCCCCC(O)=O HIQAWCBKWSQMRQ-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- IZUBVNGHMOTZBX-UHFFFAOYSA-N 2,2,2-tributoxyethyl 3-oxobutanoate;zirconium Chemical compound [Zr].CCCCOC(OCCCC)(OCCCC)COC(=O)CC(C)=O IZUBVNGHMOTZBX-UHFFFAOYSA-N 0.000 description 1
- MQXNNWDXHFBFEB-UHFFFAOYSA-N 2,2-bis(2-hydroxyphenyl)propane Chemical compound C=1C=CC=C(O)C=1C(C)(C)C1=CC=CC=C1O MQXNNWDXHFBFEB-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
- VXHYVVAUHMGCEX-UHFFFAOYSA-N 2-(2-hydroxyphenoxy)phenol Chemical compound OC1=CC=CC=C1OC1=CC=CC=C1O VXHYVVAUHMGCEX-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 1
- BXGYYDRIMBPOMN-UHFFFAOYSA-N 2-(hydroxymethoxy)ethoxymethanol Chemical compound OCOCCOCO BXGYYDRIMBPOMN-UHFFFAOYSA-N 0.000 description 1
- GQTBMBMBWQJACJ-UHFFFAOYSA-N 2-[(4-butan-2-ylphenoxy)methyl]oxirane Chemical compound C1=CC(C(C)CC)=CC=C1OCC1OC1 GQTBMBMBWQJACJ-UHFFFAOYSA-N 0.000 description 1
- CUFXMPWHOWYNSO-UHFFFAOYSA-N 2-[(4-methylphenoxy)methyl]oxirane Chemical compound C1=CC(C)=CC=C1OCC1OC1 CUFXMPWHOWYNSO-UHFFFAOYSA-N 0.000 description 1
- PEHXKUVLLWGBJS-UHFFFAOYSA-N 2-[1-(2-hydroxyphenyl)ethyl]phenol Chemical compound C=1C=CC=C(O)C=1C(C)C1=CC=CC=C1O PEHXKUVLLWGBJS-UHFFFAOYSA-N 0.000 description 1
- KUAUJXBLDYVELT-UHFFFAOYSA-N 2-[[2,2-dimethyl-3-(oxiran-2-ylmethoxy)propoxy]methyl]oxirane Chemical compound C1OC1COCC(C)(C)COCC1CO1 KUAUJXBLDYVELT-UHFFFAOYSA-N 0.000 description 1
- KTXWGMUMDPYXNN-UHFFFAOYSA-N 2-ethylhexan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCCC(CC)C[O-].CCCCC(CC)C[O-].CCCCC(CC)C[O-].CCCCC(CC)C[O-] KTXWGMUMDPYXNN-UHFFFAOYSA-N 0.000 description 1
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- IWRZKNMUSBNOOD-UHFFFAOYSA-N 2-methyl-4-(oxiran-2-ylmethoxy)-n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound C=1C=C(N(CC2OC2)CC2OC2)C(C)=CC=1OCC1CO1 IWRZKNMUSBNOOD-UHFFFAOYSA-N 0.000 description 1
- OVEUFHOBGCSKSH-UHFFFAOYSA-N 2-methyl-n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound CC1=CC=CC=C1N(CC1OC1)CC1OC1 OVEUFHOBGCSKSH-UHFFFAOYSA-N 0.000 description 1
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 1
- VEGUCZXWLYWJFN-UHFFFAOYSA-N 3-[(3-hydroxy-2-methylphenyl)methyl]-2-methylphenol Chemical compound CC1=C(O)C=CC=C1CC1=CC=CC(O)=C1C VEGUCZXWLYWJFN-UHFFFAOYSA-N 0.000 description 1
- ZUESTMNQCYNCPP-UHFFFAOYSA-N 3-[2-(3-hydroxy-2-methylphenyl)propan-2-yl]-2-methylphenol Chemical compound CC1=C(O)C=CC=C1C(C)(C)C1=CC=CC(O)=C1C ZUESTMNQCYNCPP-UHFFFAOYSA-N 0.000 description 1
- OXYZDRAJMHGSMW-UHFFFAOYSA-N 3-chloropropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCCl OXYZDRAJMHGSMW-UHFFFAOYSA-N 0.000 description 1
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 1
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 1
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- VWGKEVWFBOUAND-UHFFFAOYSA-N 4,4'-thiodiphenol Chemical compound C1=CC(O)=CC=C1SC1=CC=C(O)C=C1 VWGKEVWFBOUAND-UHFFFAOYSA-N 0.000 description 1
- AHIPJALLQVEEQF-UHFFFAOYSA-N 4-(oxiran-2-ylmethoxy)-n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound C1OC1COC(C=C1)=CC=C1N(CC1OC1)CC1CO1 AHIPJALLQVEEQF-UHFFFAOYSA-N 0.000 description 1
- HDPBBNNDDQOWPJ-UHFFFAOYSA-N 4-[1,2,2-tris(4-hydroxyphenyl)ethyl]phenol Chemical compound C1=CC(O)=CC=C1C(C=1C=CC(O)=CC=1)C(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 HDPBBNNDDQOWPJ-UHFFFAOYSA-N 0.000 description 1
- OXRFNJSKALBWCF-UHFFFAOYSA-N 4-[4,4-bis(4-hydroxyphenyl)butan-2-yl]phenol Chemical compound C=1C=C(O)C=CC=1C(C)CC(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 OXRFNJSKALBWCF-UHFFFAOYSA-N 0.000 description 1
- OECTYKWYRCHAKR-UHFFFAOYSA-N 4-vinylcyclohexene dioxide Chemical compound C1OC1C1CC2OC2CC1 OECTYKWYRCHAKR-UHFFFAOYSA-N 0.000 description 1
- OXQXGKNECHBVMO-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptane-4-carboxylic acid Chemical compound C1C(C(=O)O)CCC2OC21 OXQXGKNECHBVMO-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- BLJDJVLDTYVWCL-UHFFFAOYSA-N CC1CC2OC2CC1CC1(C(O)=O)CCCCC1C Chemical compound CC1CC2OC2CC1CC1(C(O)=O)CCCCC1C BLJDJVLDTYVWCL-UHFFFAOYSA-N 0.000 description 1
- YQEVIZPKEOELNL-UHFFFAOYSA-N CCCCO[Zr] Chemical compound CCCCO[Zr] YQEVIZPKEOELNL-UHFFFAOYSA-N 0.000 description 1
- GWYDZVYZTDJZQB-UHFFFAOYSA-N CCCO[Zr] Chemical compound CCCO[Zr] GWYDZVYZTDJZQB-UHFFFAOYSA-N 0.000 description 1
- 239000009261 D 400 Substances 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
- DRNPGEPMHMPIQU-UHFFFAOYSA-N O.[Ti].[Ti].CCCCO.CCCCO.CCCCO.CCCCO.CCCCO.CCCCO Chemical compound O.[Ti].[Ti].CCCCO.CCCCO.CCCCO.CCCCO.CCCCO.CCCCO DRNPGEPMHMPIQU-UHFFFAOYSA-N 0.000 description 1
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 1
- 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 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 229920000388 Polyphosphate Polymers 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 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
- 125000003277 amino group Chemical group 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 229920006231 aramid fiber Polymers 0.000 description 1
- 150000008378 aryl ethers Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- 229940092738 beeswax Drugs 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000002457 bidirectional effect Effects 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- LMMDJMWIHPEQSJ-UHFFFAOYSA-N bis[(3-methyl-7-oxabicyclo[4.1.0]heptan-4-yl)methyl] hexanedioate Chemical compound C1C2OC2CC(C)C1COC(=O)CCCCC(=O)OCC1CC2OC2CC1C LMMDJMWIHPEQSJ-UHFFFAOYSA-N 0.000 description 1
- 238000000071 blow moulding Methods 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000004204 candelilla wax Substances 0.000 description 1
- 235000013868 candelilla wax Nutrition 0.000 description 1
- 229940073532 candelilla wax Drugs 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000004203 carnauba wax Substances 0.000 description 1
- 235000013869 carnauba wax Nutrition 0.000 description 1
- 239000011280 coal tar Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 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 1
- 150000004985 diamines Chemical class 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- IRDLUHRVLVEUHA-UHFFFAOYSA-N diethyl dithiophosphate Chemical compound CCOP(S)(=S)OCC IRDLUHRVLVEUHA-UHFFFAOYSA-N 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- HTDKEJXHILZNPP-UHFFFAOYSA-N dioctyl hydrogen phosphate Chemical compound CCCCCCCCOP(O)(=O)OCCCCCCCC HTDKEJXHILZNPP-UHFFFAOYSA-N 0.000 description 1
- XHWQYYPUYFYELO-UHFFFAOYSA-N ditridecyl phosphite Chemical compound CCCCCCCCCCCCCOP([O-])OCCCCCCCCCCCCC XHWQYYPUYFYELO-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- NCXTWAVJIHJVRV-UHFFFAOYSA-N ethane-1,2-diol;16-methylheptadecanoic acid;titanium Chemical compound [Ti].OCCO.CC(C)CCCCCCCCCCCCCCC(O)=O.CC(C)CCCCCCCCCCCCCCC(O)=O NCXTWAVJIHJVRV-UHFFFAOYSA-N 0.000 description 1
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 229940093858 ethyl acetoacetate Drugs 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000009730 filament winding Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 238000009787 hand lay-up Methods 0.000 description 1
- IUJAMGNYPWYUPM-UHFFFAOYSA-N hentriacontane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC IUJAMGNYPWYUPM-UHFFFAOYSA-N 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 239000012182 japan wax Substances 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- ITNVWQNWHXEMNS-UHFFFAOYSA-N methanolate;titanium(4+) Chemical compound [Ti+4].[O-]C.[O-]C.[O-]C.[O-]C ITNVWQNWHXEMNS-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 239000012170 montan wax Substances 0.000 description 1
- JAYXSROKFZAHRQ-UHFFFAOYSA-N n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound C1OC1CN(C=1C=CC=CC=1)CC1CO1 JAYXSROKFZAHRQ-UHFFFAOYSA-N 0.000 description 1
- LIBWSLLLJZULCP-UHFFFAOYSA-N n-(3-triethoxysilylpropyl)aniline Chemical compound CCO[Si](OCC)(OCC)CCCNC1=CC=CC=C1 LIBWSLLLJZULCP-UHFFFAOYSA-N 0.000 description 1
- CXXISLZOPXKTTK-UHFFFAOYSA-N n-methyl-4-[[4-[methyl(oxiran-2-ylmethyl)amino]phenyl]methyl]-n-(oxiran-2-ylmethyl)aniline Chemical compound C=1C=C(CC=2C=CC(=CC=2)N(C)CC2OC2)C=CC=1N(C)CC1CO1 CXXISLZOPXKTTK-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- KQJBQMSCFSJABN-UHFFFAOYSA-N octadecan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCCCCCCCCCCCCCCCC[O-].CCCCCCCCCCCCCCCCCC[O-].CCCCCCCCCCCCCCCCCC[O-].CCCCCCCCCCCCCCCCCC[O-] KQJBQMSCFSJABN-UHFFFAOYSA-N 0.000 description 1
- 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 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 239000012169 petroleum derived wax Substances 0.000 description 1
- 235000019381 petroleum wax Nutrition 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 1
- 229960001553 phloroglucinol Drugs 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- XPGAWFIWCWKDDL-UHFFFAOYSA-N propan-1-olate;zirconium(4+) Chemical compound [Zr+4].CCC[O-].CCC[O-].CCC[O-].CCC[O-] XPGAWFIWCWKDDL-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002990 reinforced plastic Substances 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000012177 spermaceti Substances 0.000 description 1
- 229940084106 spermaceti Drugs 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- BJQWBACJIAKDTJ-UHFFFAOYSA-N tetrabutylphosphanium Chemical compound CCCC[P+](CCCC)(CCCC)CCCC BJQWBACJIAKDTJ-UHFFFAOYSA-N 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- NBXZNTLFQLUFES-UHFFFAOYSA-N triethoxy(propyl)silane Chemical compound CCC[Si](OCC)(OCC)OCC NBXZNTLFQLUFES-UHFFFAOYSA-N 0.000 description 1
- UDUKMRHNZZLJRB-UHFFFAOYSA-N triethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OCC)(OCC)OCC)CCC2OC21 UDUKMRHNZZLJRB-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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
- C08G59/50—Amines
- C08G59/56—Amines together with other curing agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/04—Reinforcing macromolecular compounds with loose or coherent fibrous material
Definitions
- the present invention relates to a resin composition for fiber-reinforced plastics and fiber-reinforced plastics using the composition, and more particularly, fiber-reinforced plastics containing epoxy resin, polyoxyalkylene polyamine, and a salt compound that is liquid at room temperature. Regarding.
- thermosetting epoxy resin unsaturated polyester, polyamide resin, or phenolic resin
- Fiber-reinforced plastics produced by this method are widely used as materials for structures such as aircraft and ships, and sporting goods such as tennis rackets and golf clubs.
- Epoxy resin used as a reinforcing material is often used as a well-balanced material because it is not only excellent in adhesiveness, heat resistance, and chemical resistance, but also inexpensive.
- Patent Documents 1 to 3, etc. propose an epoxy resin composition for fiber reinforcement consisting of an epoxy resin, an acid anhydride, and a curing catalyst, and describe an imidazole-based catalyst as the curing catalyst.
- JP-A-8-156115 Japanese Unexamined Patent Application Publication No. 2008-38082 JP 2015-3938 A
- an object of the present invention is to provide a resin composition for fiber-reinforced plastics that is suitable for improving the strength of fiber-reinforced plastics, has an excellent balance between pot life and curability, and has excellent non-coloring properties. That's what it is.
- the inventors of the present invention have made intensive studies to achieve the above objects, and have developed a resin composition for fiber-reinforced plastics having excellent curability and non-coloring property by combining an epoxy resin, a polyoxyalkylene polyamine and a specific phosphonium salt.
- the present invention was arrived at by discovering that a product can be obtained.
- the present invention provides a fiber containing at least one compound selected from component (A): epoxy resin, component (B): polyoxyalkylene polyamine, and component (C): a compound represented by the following formula (1).
- a resin composition for reinforced plastics is provided.
- R 1 to R 6 each independently represent a hydrocarbon group having 1 to 10 carbon atoms, and X 1 to X 4 each independently represent an oxygen atom or a sulfur atom.
- the present invention also provides a fiber-reinforced plastic containing the resin composition for fiber-reinforced plastics.
- the resin composition for fiber-reinforced plastics of the present invention is excellent in curability and non-coloring properties, and the fiber-reinforced plastics obtained therefrom provide various moldings with excellent aesthetic appearance from the viewpoint of being excellent in non-coloring properties. It is possible.
- epoxy resins as component (A) include polyglycidyl ether compounds of mononuclear polyhydric phenol compounds such as hydroquinone, resorcinol, pyrocatechol and phloroglucinol; methylenebis(orthocresol), ethylidenebisphenol, isopropylidenebisphenol (bisphenol A), isopropylidenebis(orthocresol), tetrabromobisphenol A, 1,3-bis(4-hydroxycumylbenzene), 1,4-bis( 4-hydroxycumylbenzene), 1,1,3-tris(4-hydroxyphenyl)butane, 1,1,2,2-tetra(4-hydroxyphenyl)ethane, thiobisphenol, sulfobisphenol, oxybisphenol, phenol Polyglycidyl ether compounds of polynuclear polyhydric phenol compounds such as novolac, ortho-cresol novolak, ethylphenol novolak, but
- N,N-diglycidylaniline bis(4-(N-methyl-N-glycidylamino)phenyl)methane, diglycidylorthotoluidine, N,N-bis(2,3-epoxypropyl) -4-(2,3-epoxypropoxy)-2-methylaniline, N,N-bis(2,3-epoxypropyl)-4-(2,3-epoxypropoxy)aniline, N,N,N', Epoxy compounds having a glycidylamino group such as N'-tetra(2,3-epoxypropyl)-4,4-diaminodiphenylmethane; vinylcyclohexene diepoxide, cyclopentanediene diepoxide, 3,4-epoxycyclohexylmethyl-3, Epoxidized products of cyclic olefin compounds such as 4-epoxycyclohexanecarboxylate, 3,
- these epoxy resins are those internally crosslinked with a prepolymer having an isocyanate terminal, or those having a high molecular weight with a polyvalent active hydrogen compound (polyhydric phenol, polyamine, carbonyl group-containing compound, polyphosphate ester, etc.). It's okay.
- These epoxy resins may be used alone or in combination of two or more. In the present invention, an epoxy resin having an average of more than 1.1 epoxy groups per molecule is preferred, and an epoxy resin having two or more epoxy groups per molecule is particularly preferred.
- the epoxy resins preferably contains at least one of a polyglycidyl ether compound of a polynuclear polyhydric phenol compound and a polyglycidyl ether compound of a polyhydric alcohol compound, and more preferably contains a polyglycidyl ether compound of a polynuclear polyhydric phenol compound. It is more preferable to contain a polyglycidyl ether compound of a polynuclear polyhydric phenol compound as a main component, and it is particularly preferable to contain a bisphenol type epoxy resin as a main component.
- the main component means that the content in the epoxy resin is more than 50% by mass.
- a bisphenol-type epoxy resin is one having a bisphenol structure such as a polyglycidyl ether compound of bisphenols such as bisphenol A.
- a resin containing a bisphenol type epoxy resin as a main component is preferable because it provides excellent curability and physical properties of the cured product.
- the resin composition of the present invention is used for fiber-reinforced plastics, it is preferable to use an epoxy resin that is liquid at 25° C. from the viewpoint of permeability into fiber materials.
- the amount of the epoxy resin used is not particularly limited. ⁇ 80 parts by mass.
- the polyoxyalkylene polyamine which is the component (B) used in the present invention, is a compound having a polyoxyalkylene skeleton and two or more amino groups, and there are no particular restrictions on its molecular structure, molecular weight, and the like.
- polyoxyalkylene polyamine examples include polyoxypropylene diamine, trimethylolpropane poly(oxypropylene)triamine, glycerylpoly(oxypropylene)triamine, polyoxyethylenediamine, trimethylolpropanepoly(oxyethylene)triamine, glycerylpoly( oxyethylene) triamine and the like.
- polyoxypropylenediamine as the component (B) from the viewpoint of improving curability and physical properties of the cured product.
- the weight average molecular weight of the polyoxyalkylene polyamine which is the component (B) is preferably 200 to 5000, more preferably 200 to 2000, and particularly 200 to 500 is preferred.
- the weight average molecular weight refers to the polystyrene equivalent weight average molecular weight (Mw) measured by gel permeation chromatography (GPC).
- component (B) Commercially available products of component (B) include, for example, Huntsman's Jeffamine D-230, Jeffamine D-400, Jeffamine D-2000, Jeffamine D-4000, Jeffamine T-403, and Jeffamine T. -3000, Jeffamine T-5000 and the like.
- the amount of polyoxyalkylene polyamine used as component (B) is preferably 1 to 50 parts by mass, particularly preferably 5 to 30 parts by mass, per 100 parts by mass of the epoxy resin as component (A).
- the amount of polyoxyalkylene polyamine used as component (B) is preferably 1 to 50 parts by mass, particularly preferably 5 to 30 parts by mass, per 100 parts by mass of the epoxy resin as component (A).
- the amount of the polyoxyalkylene polyamine used as the component (B) is not particularly limited, but is preferably 0.01 to 50% by mass, more preferably 0.05%, in the resin composition for fiber-reinforced plastics. to 40% by mass, particularly preferably 0.1 to 30% by mass.
- the (C) component used in the present invention is a compound represented by the following formula (1) and functions as a curing catalyst for the (A) and (B) components.
- R 1 to R 6 each independently represent a hydrocarbon group having 1 to 10 carbon atoms, and X 1 to X 4 each independently represent an oxygen atom or a sulfur atom.
- examples of hydrocarbon groups having 1 to 10 carbon atoms represented by R 1 to R 6 include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, secondary Butyl group, tert-butyl group, pentyl group, hexyl group, heptyl group, octyl group, isooctyl group, tert-octyl group, 2-ethylhexyl group, nonyl group, isononyl group, decyl group, isodecyl group, phenyl group, benzyl group and a cyclohexyl group.
- R 1 to R 4 are each independently preferably a methyl group or a butyl group
- R 5 and R 6 are preferably each independently a methyl group or an ethyl group. This is because a resin composition having an excellent balance of curability and non-coloring property can be obtained.
- Specific examples of preferred compounds represented by the general formula (1) as the component (C) include compounds represented by the following general formula (1a) or general formula (1b).
- the compounding amount of the compound represented by the general formula (1), which is the component (C), is not particularly limited, but is 0.00 per 100 parts by mass of the polyoxyalkylene polyamine, which is the component (B). 01 to 20 parts by weight, preferably 0.05 to 15 parts by weight, particularly preferably 0.1 to 10 parts by weight.
- component (C) By using 0.01 parts by mass or more of the compound represented by the general formula (1) as component (C), sufficient curability can be obtained, and by using 20 parts by mass or less, sufficient storage can be achieved. Stability can be obtained.
- the amount of the compound represented by the general formula (1), which is the component (C), is not particularly limited, but is preferably 0.005 to 10% by mass in the resin composition for fiber-reinforced plastics, More preferably 0.01 to 8% by mass, particularly preferably 0.05 to 5% by mass.
- the present invention further contains a silane coupling agent as the component (D) because good adhesion to the fiber material can be obtained.
- the silane coupling agent include ⁇ -aminopropyltriethoxysilane, N- ⁇ -(aminoethyl)- ⁇ -aminopropyltriethoxysilane, N- ⁇ -(aminoethyl)-N'- ⁇ -( aminoethyl)- ⁇ -aminopropyltriethoxysilane, ⁇ -anilinopropyltriethoxysilane, ⁇ -glycidoxypropyltriethoxysilane, ⁇ -(3,4-epoxycyclohexyl)ethyltriethoxysilane, vinyltriethoxysilane , N- ⁇ -(N-vinylbenzylaminoethyl)- ⁇ -aminopropyltriethoxysilane, ⁇ -methacryloxyprop
- ⁇ -aminopropyltrimethoxysilane and/or ⁇ -glycidoxypropyltrimethoxysilane are more preferably added because they are readily available and inexpensive. Most preferably, sidoxypropyltrimethoxysilane is added.
- the amount of the silane coupling agent, component (D), is not particularly limited, but is 0.1 to 50 parts by mass with respect to 100 parts by mass of the epoxy resin, component (A). is preferred. From the viewpoint of good miscibility with the resin and improved adhesion to the fiber, it is particularly preferable to add 0.5 to 30 parts by mass, particularly 1 to 20 parts by mass.
- the amount of the silane coupling agent used as the component (D) is not particularly limited, but is preferably 0.005 to 10% by mass, more preferably 0.01%, in the resin composition for fiber-reinforced plastics. to 8% by weight, particularly preferably 0.05 to 5% by weight.
- a reactive diluent as component (E) may be used in combination in order to adjust the viscosity to a desired level.
- the reactive diluent is incorporated into the cured product after the resin composition is cured, so that it does not affect the physical properties of the cured product.
- Reactive diluents for epoxy resin compositions include diluents having an epoxy group in the molecule.
- reactive diluents examples include n-butyl glycidyl ether, C 12 -C 14 alkyl glycidyl ether, allyl glycidyl ether, 2-ethylhexyl glycidyl ether, styrene oxide, phenyl glycidyl ether, cresyl glycidyl ether, Examples include monoglycidyl ether compounds such as p-sec-butylphenyl glycidyl ether, t-butylphenyl glycidyl ether, glycidyl methacrylate, and tertiary carboxylic acid glycidyl esters.
- Additives may be used in combination with the resin composition for fiber-reinforced plastics of the present invention, if necessary.
- the above additives include non-reactive diluents (plasticizers) such as dioctyl phthalate, dibutyl phthalate, benzyl alcohol and coal tar; pigments; candelilla wax, carnauba wax, Japan wax, ivory wax, beeswax, lanolin , spermaceti, montan wax, petroleum wax, fatty acid wax, fatty acid ester, fatty acid ether, aromatic ester, lubricant such as aromatic ether; thickener; thixotropic agent; antioxidant; light stabilizer; ultraviolet absorber ;flame retardants; antifoaming agents;
- plasticizers such as dioctyl phthalate, dibutyl phthalate, benzyl alcohol and coal tar
- pigments candelilla wax, carnauba wax, Japan wax, ivory wax, beesw
- the resin composition for fiber-reinforced plastics of the present invention is used for fiber-reinforced plastics, it is preferably liquid at 25°C, and particularly preferably has a viscosity of 100 to 3000 Pa ⁇ s.
- the resin composition for fiber-reinforced plastics of the present invention is suitable as a matrix resin for fiber-reinforced plastics having reinforcing fibers such as carbon fiber and glass fiber.
- the type of reinforcing fiber is not particularly limited, and for example, carbon fiber, glass fiber, aramid fiber, boron fiber, alumina fiber, silicone carbide fiber, etc. may be used alone, or two or more types of hybrid fibers may be used. .
- Examples of the form of the reinforcing fibers include so-called tow sheets in which high-strength, high-modulus fibers are arranged in one direction, unidirectional or bidirectional fabrics in which the fiber threads are arranged in one or two directions, Examples include triaxial woven fabrics arranged in three directions and multiaxial woven fabrics arranged in multiple directions.
- the fibers are preferably arranged so as to secure an appropriate gap between the strands in order to improve the resin impregnation property of the base material.
- the method for molding fiber-reinforced plastics using the resin composition for fiber-reinforced plastics of the present invention is not particularly limited, but examples thereof include extrusion molding, blow molding, compression molding, and vacuum molding. , injection molding, RTM (resin transfer molding) molding, VaRTM (vacuum assist resin transfer molding) molding, laminate molding, hand lay-up molding, filament winding molding, and the like.
- the amount of the cured product of the resin composition for fiber-reinforced plastic contained in the fiber-reinforced plastic is preferably 5 to 95% by mass, particularly preferably 10 to 80% by mass, further preferably 20 to 70% by mass. It is preferable because it can exhibit excellent physical properties by being used in.
- the fiber-reinforced plastic obtained using the resin composition for fiber-reinforced plastic of the present invention can be used for various purposes.
- general industrial applications such as structural materials for moving bodies such as automobiles, ships and railway vehicles, drive shafts, leaf springs, windmill blades, pressure vessels, flywheels, papermaking rollers, roofing materials, cables, and repair and reinforcement materials;
- Aerospace applications such as fuselages, main wings, tail wings, rotor blades, fairings, cowls, doors, seats, interior materials, motor cases, antennas; golf shafts, fishing rods, tennis and badminton rackets, hockey sticks, and so on.
- Sports applications such as ski pole applications.
- Example 1 In a 500 mL disposable cup, 98.6 g of ADEKA RESIN EP-4100E (manufactured by ADEKA Co., Ltd.; bisphenol A type epoxy resin, epoxy equivalent: 190 g / eq.), 32 g of Jeffamine D-230 (manufactured by Huntsman; polypropylene polyamine) , 2 g of hishicolin PX-4ET (manufactured by Nippon Kagaku Kogyo; tetrabutylphosphonium O,O-diethylphosphorodithioate) and KBM-403 (manufactured by Shin-Etsu Chemical Co., Ltd., ⁇ -glycidoxypropyltrimethoxysilane) 1.4 g was added and stirred with a spatula for 5 minutes at 25°C. Thereafter, the mixture was further stirred using a planetary stirrer to obtain a resin composition.
- ADEKA RESIN EP-4100E manufactured by
- Example 2 In a 500 mL disposable cup, 83.9 g of ADEKA RESIN EP-4100E (manufactured by ADEKA Corporation; bisphenol A type epoxy resin, epoxy equivalent: 190 g / eq.), ADEKA GLYCIROL ED-523T (manufactured by ADEKA Corporation; neopentyl Glycol-type epoxy resin: 14.8 g of epoxy equivalent 140 g / eq.), 32 g of Jeffamine D-230 (manufactured by Huntsman; polypropylene polyamine), Hishikorin PX-4ET (manufactured by Nippon Kagaku Kogyo; tetrabutylphosphonium O, O- 2 g of diethyl phosphorodithioate) and 1.3 g of KBM-403 (manufactured by Shin-Etsu Chemical Co., Ltd., ⁇ -glycidoxypropyltrimethoxysilane) were added and
- Example 3 79.0 g of ADEKA RESIN EP-4100E (manufactured by ADEKA Corporation; bisphenol A type epoxy resin, epoxy equivalent: 190 g/eq.) and 30 of Jeffamine D-230 (manufactured by Huntsman; polypropylene polyamine) are placed in a 500 mL disposable cup.
- Example 4 In a 500 mL disposable cup, 74.0 g of ADEKA RESIN EP-4100E (manufactured by ADEKA Co., Ltd.; bisphenol A type epoxy resin, epoxy equivalent: 190 g / eq.), 30 of Jeffamine D-230 (manufactured by Huntsman; polypropylene polyamine) 6 g, Hishikorin PX-4ET (manufactured by Nippon Kagaku Kogyo; tetrabutylphosphonium O,O-diethylphosphorodithioate) 2 g, KBM-403 (manufactured by Shin-Etsu Chemical Co., Ltd., ⁇ -glycidoxypropyltrimethoxysilane ) and 24.8 g of ADEKA GLYCIROL ED-509E (manufactured by ADEKA; t-butylphenylglycidyl ether: epoxy equivalent: 210 g/eq.) were
- the resin composition for fiber-reinforced plastics of the present invention has excellent curability, and the fiber-reinforced plastic obtained using it has excellent non-coloring properties.
- the resin composition for fiber-reinforced plastics of the present invention can provide fiber-reinforced plastics with excellent curability and excellent non-coloring properties, it is possible to provide molded articles with excellent appearance.
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Materials Engineering (AREA)
- Epoxy Resins (AREA)
Abstract
A purpose of the present invention is to provide a resin composition for fiber-reinforced plastics which is suitable for improving the strength of fiber-reinforced plastics, has an excellent balance between pot life and curability, and has excellent non-coloring properties. This resin composition comprises (A) component, which is an epoxy resin, (B) component, which is a polyoxyalkylene-polyamine, and (C) component, which is at least one compound selected from among compounds represented by formula (1). (In formula (1), R1 to R6 each independently represent a C1-C10 hydrocarbon group and X1 to X4 each independently represent an oxygen atom or a sulfur atom.)
Description
本発明は、繊維強化プラスチック用樹脂組成物、及び該組成物を用いてなる繊維強化プラスチックに関し、詳しくは、エポキシ樹脂、ポリオキシアルキレンポリアミン及び室温で液状の塩化合物を含有してなる繊維強化プラスチックに関する。
TECHNICAL FIELD The present invention relates to a resin composition for fiber-reinforced plastics and fiber-reinforced plastics using the composition, and more particularly, fiber-reinforced plastics containing epoxy resin, polyoxyalkylene polyamine, and a salt compound that is liquid at room temperature. Regarding.
炭素繊維やガラス繊維等の繊維材料に対し、補強材として熱硬化性のエポキシ樹脂や、不飽和ポリエステル、ポリアミド樹脂、又はフェノール樹脂を用いて成型物を作る方法は周知である。この方法を用いた繊維強化プラスチックは、航空機、船舶などの構造体の材料や、テニスラケット、ゴルフクラブ等のスポーツ用品に広く使われている。補強材として用いられるエポキシ樹脂は、接着性、耐熱性、耐薬品性に優れているだけでなく安価であることから、バランスの良い材料として使用されることが多い。
It is well known how to make moldings using thermosetting epoxy resin, unsaturated polyester, polyamide resin, or phenolic resin as a reinforcing material for fiber materials such as carbon fiber and glass fiber. Fiber-reinforced plastics produced by this method are widely used as materials for structures such as aircraft and ships, and sporting goods such as tennis rackets and golf clubs. Epoxy resin used as a reinforcing material is often used as a well-balanced material because it is not only excellent in adhesiveness, heat resistance, and chemical resistance, but also inexpensive.
特許文献１～３などには、エポキシ樹脂、酸無水物、硬化触媒からなる繊維強化用のエポキシ樹脂組成物が提案されているが、硬化触媒としてはイミダゾール系触媒が記載されている。
Patent Documents 1 to 3, etc., propose an epoxy resin composition for fiber reinforcement consisting of an epoxy resin, an acid anhydride, and a curing catalyst, and describe an imidazole-based catalyst as the curing catalyst.
これまでに提案された方法では、材料が着色してしまうという問題があった。
従って、本発明の目的は、繊維強化プラスチックの強度を向上させるのに適しており、ポットライフと硬化性のバランスに優れ、且つ非着色性に優れた、繊維強化プラスチック用樹脂組成物を提供することにある。 The methods proposed so far have a problem that the material is colored.
Accordingly, an object of the present invention is to provide a resin composition for fiber-reinforced plastics that is suitable for improving the strength of fiber-reinforced plastics, has an excellent balance between pot life and curability, and has excellent non-coloring properties. That's what it is.
従って、本発明の目的は、繊維強化プラスチックの強度を向上させるのに適しており、ポットライフと硬化性のバランスに優れ、且つ非着色性に優れた、繊維強化プラスチック用樹脂組成物を提供することにある。 The methods proposed so far have a problem that the material is colored.
Accordingly, an object of the present invention is to provide a resin composition for fiber-reinforced plastics that is suitable for improving the strength of fiber-reinforced plastics, has an excellent balance between pot life and curability, and has excellent non-coloring properties. That's what it is.
本発明者等は上記の諸目的を達成するために鋭意検討し、エポキシ樹脂、ポリオキシアルキレンポリアミン及び特定のホスホニウム塩を組み合わせることにより、硬化性及び非着色性に優れた繊維強化プラスチック用樹脂組成物が得られることを見出し、本発明に到達した。
The inventors of the present invention have made intensive studies to achieve the above objects, and have developed a resin composition for fiber-reinforced plastics having excellent curability and non-coloring property by combining an epoxy resin, a polyoxyalkylene polyamine and a specific phosphonium salt. The present invention was arrived at by discovering that a product can be obtained.
即ち、本発明は、（Ａ）成分：エポキシ樹脂、（Ｂ）成分：ポリオキシアルキレンポリアミン及び（Ｃ）成分：下記式（１）で表される化合物の中から選ばれる少なくとも一種を含有する繊維強化プラスチック用樹脂組成物を提供するものである。
That is, the present invention provides a fiber containing at least one compound selected from component (A): epoxy resin, component (B): polyoxyalkylene polyamine, and component (C): a compound represented by the following formula (1). A resin composition for reinforced plastics is provided.
（式中、Ｒ１～Ｒ６は、それぞれ独立して、炭素数１～１０の炭化水素基を表し、Ｘ１～Ｘ４は、それぞれ独立して、酸素原子又は硫黄原子を表す。）
(In the formula, R 1 to R 6 each independently represent a hydrocarbon group having 1 to 10 carbon atoms, and X 1 to X 4 each independently represent an oxygen atom or a sulfur atom.)
また、本発明は、前記繊維強化プラスチック用樹脂組成物を含有する繊維強化プラスチックを提供するものである。
The present invention also provides a fiber-reinforced plastic containing the resin composition for fiber-reinforced plastics.
本発明の繊維強化プラスチック用樹脂組成物は、硬化性及び非着色性に優れたものであり、これから得られる繊維強化プラスチックは、非着色性に優れるという点から美観に優れた各種成形品を提供しうるものである。
The resin composition for fiber-reinforced plastics of the present invention is excellent in curability and non-coloring properties, and the fiber-reinforced plastics obtained therefrom provide various moldings with excellent aesthetic appearance from the viewpoint of being excellent in non-coloring properties. It is possible.
（Ａ）成分であるエポキシ樹脂としては、例えば、ハイドロキノン、レゾルシン、ピロカテコール、フロログルクシノールなどの単核多価フェノール化合物のポリグリシジルエーテル化合物；ジヒドロキシナフタレン、ビフェノール、メチレンビスフェノール（ビスフェノールＦ）、メチレンビス（オルトクレゾール）、エチリデンビスフェノール、イソプロピリデンビスフェノール（ビスフェノールＡ）、イソプロピリデンビス（オルトクレゾール）、テトラブロモビスフェノールＡ、１，３－ビス（４－ヒドロキシクミルベンゼン）、１，４－ビス（４－ヒドロキシクミルベンゼン）、１，１，３－トリス（４－ヒドロキシフェニル）ブタン、１，１，２，２－テトラ（４－ヒドロキシフェニル）エタン、チオビスフェノール、スルホビスフェノール、オキシビスフェノール、フェノールノボラック、オルソクレゾールノボラック、エチルフェノールノボラック、ブチルフェノールノボラック、オクチルフェノールノボラック、レゾルシンノボラック、テルペンフェノール等の多核多価フェノール化合物のポリグリシジルエーテル化合物；エチレングリコール、プロピレングリコール、ブチレングリコール、ネオペンチルグリコール、ヘキサンジオール、ポリエチレングリコール、ポリプロピレングリコール、チオグリコール、ジシクロペンタジエンジメタノール、２，２－ビス（４－ヒドロキシシクロヘキシル）プロパン（水素化ビスフェノールＡ）、グリセリン、トリメチロールプロパン、ペンタエリスリトール、ソルビトール、ビスフェノールＡ－アルキレンオキシド付加物などの多価アルコール化合物のポリグリシジルエーテル化合物；マレイン酸、フマル酸、イタコン酸、コハク酸、グルタル酸、スベリン酸、アジピン酸、アゼライン酸、セバシン酸、ダイマー酸、トリマー酸、フタル酸、イソフタル酸、テレフタル酸、トリメリット酸、トリメシン酸、ピロメリット酸、テトラヒドロフタル酸、エンドメチレンテトラヒドロフタル酸等の脂肪族、芳香族又は脂環族多塩基酸のグリシジルエステル化合物及びグリシジルメタクリレートの単独重合体又は共重合体；Ｎ，Ｎ－ジグリシジルアニリン、ビス（４－（Ｎ－メチル－Ｎ－グリシジルアミノ）フェニル）メタン、ジグリシジルオルトトルイジン、Ｎ，Ｎ－ビス（２，３－エポキシプロピル）－４－（２，３－エポキシプロポキシ）－２－メチルアニリン、Ｎ，Ｎ－ビス（２，３－エポキシプロピル）－４－（２，３－エポキシプロポキシ）アニリン、Ｎ，Ｎ，Ｎ’，Ｎ’－テトラ（２，３－エポキシプロピル）－４，４－ジアミノジフェニルメタン等のグリシジルアミノ基を有するエポキシ化合物；ビニルシクロヘキセンジエポキシド、シクロペンタンジエンジエポキサイド、３，４－エポキシシクロヘキシルメチル－３，４－エポキシシクロヘキサンカルボキシレート、３，４－エポキシ－６－メチルシクロヘキシルメチル－６－メチルシクロヘキサンカルボキシレート、ビス（３，４－エポキシ－６－メチルシクロヘキシルメチル）アジペート等の環状オレフィン化合物のエポキシ化物；エポキシ化ポリブタジエン、エポキシ化スチレン－ブタジエン共重合物等のエポキシ化共役ジエン重合体；トリグリシジルイソシアヌレート等の複素環化合物が挙げられる。また、これらのエポキシ樹脂は、末端イソシアネートのプレポリマーにより内部架橋されたもの、あるいは多価の活性水素化合物（多価フェノール、ポリアミン、カルボニル基含有化合物、ポリリン酸エステル等）で高分子量化したものでもよい。
これらのエポキシ樹脂は、単独で用いてもよいし、２種類以上を併用してもよい。
本発明においては、１分子中のエポキシ基が平均１．１個を超えるエポキシ樹脂が好ましく、とりわけ１分子中に２個以上のエポキシ基を有するエポキシ樹脂を用いることが好ましい。 Examples of epoxy resins as component (A) include polyglycidyl ether compounds of mononuclear polyhydric phenol compounds such as hydroquinone, resorcinol, pyrocatechol and phloroglucinol; methylenebis(orthocresol), ethylidenebisphenol, isopropylidenebisphenol (bisphenol A), isopropylidenebis(orthocresol), tetrabromobisphenol A, 1,3-bis(4-hydroxycumylbenzene), 1,4-bis( 4-hydroxycumylbenzene), 1,1,3-tris(4-hydroxyphenyl)butane, 1,1,2,2-tetra(4-hydroxyphenyl)ethane, thiobisphenol, sulfobisphenol, oxybisphenol, phenol Polyglycidyl ether compounds of polynuclear polyhydric phenol compounds such as novolac, ortho-cresol novolak, ethylphenol novolak, butylphenol novolak, octylphenol novolak, resorcinol novolak, and terpene phenol; ethylene glycol, propylene glycol, butylene glycol, neopentyl glycol, hexanediol, Polyethylene glycol, polypropylene glycol, thioglycol, dicyclopentadiene dimethanol, 2,2-bis(4-hydroxycyclohexyl)propane (hydrogenated bisphenol A), glycerin, trimethylolpropane, pentaerythritol, sorbitol, bisphenol A-alkylene oxide Polyglycidyl ether compounds of polyhydric alcohol compounds such as adducts; maleic acid, fumaric acid, itaconic acid, succinic acid, glutaric acid, suberic acid, adipic acid, azelaic acid, sebacic acid, dimer acid, trimer acid, phthalic acid, Glycidyl ester compounds and glycidyl methacrylates of aliphatic, aromatic or alicyclic polybasic acids such as isophthalic acid, terephthalic acid, trimellitic acid, trimesic acid, pyromellitic acid, tetrahydrophthalic acid, endomethylenetetrahydrophthalic acid, etc. Combined or copolymer; N,N-diglycidylaniline, bis(4-(N-methyl-N-glycidylamino)phenyl)methane, diglycidylorthotoluidine, N,N-bis(2,3-epoxypropyl) -4-(2,3-epoxypropoxy)-2-methylaniline, N,N-bis(2,3-epoxypropyl)-4-(2,3-epoxypropoxy)aniline, N,N,N', Epoxy compounds having a glycidylamino group such as N'-tetra(2,3-epoxypropyl)-4,4-diaminodiphenylmethane; vinylcyclohexene diepoxide, cyclopentanediene diepoxide, 3,4-epoxycyclohexylmethyl-3, Epoxidized products of cyclic olefin compounds such as 4-epoxycyclohexanecarboxylate, 3,4-epoxy-6-methylcyclohexylmethyl-6-methylcyclohexanecarboxylate, and bis(3,4-epoxy-6-methylcyclohexylmethyl)adipate; epoxidized conjugated diene polymers such as epoxidized polybutadiene and epoxidized styrene-butadiene copolymers; and heterocyclic compounds such as triglycidyl isocyanurate. In addition, these epoxy resins are those internally crosslinked with a prepolymer having an isocyanate terminal, or those having a high molecular weight with a polyvalent active hydrogen compound (polyhydric phenol, polyamine, carbonyl group-containing compound, polyphosphate ester, etc.). It's okay.
These epoxy resins may be used alone or in combination of two or more.
In the present invention, an epoxy resin having an average of more than 1.1 epoxy groups per molecule is preferred, and an epoxy resin having two or more epoxy groups per molecule is particularly preferred.
これらのエポキシ樹脂は、単独で用いてもよいし、２種類以上を併用してもよい。
本発明においては、１分子中のエポキシ基が平均１．１個を超えるエポキシ樹脂が好ましく、とりわけ１分子中に２個以上のエポキシ基を有するエポキシ樹脂を用いることが好ましい。 Examples of epoxy resins as component (A) include polyglycidyl ether compounds of mononuclear polyhydric phenol compounds such as hydroquinone, resorcinol, pyrocatechol and phloroglucinol; methylenebis(orthocresol), ethylidenebisphenol, isopropylidenebisphenol (bisphenol A), isopropylidenebis(orthocresol), tetrabromobisphenol A, 1,3-bis(4-hydroxycumylbenzene), 1,4-bis( 4-hydroxycumylbenzene), 1,1,3-tris(4-hydroxyphenyl)butane, 1,1,2,2-tetra(4-hydroxyphenyl)ethane, thiobisphenol, sulfobisphenol, oxybisphenol, phenol Polyglycidyl ether compounds of polynuclear polyhydric phenol compounds such as novolac, ortho-cresol novolak, ethylphenol novolak, butylphenol novolak, octylphenol novolak, resorcinol novolak, and terpene phenol; ethylene glycol, propylene glycol, butylene glycol, neopentyl glycol, hexanediol, Polyethylene glycol, polypropylene glycol, thioglycol, dicyclopentadiene dimethanol, 2,2-bis(4-hydroxycyclohexyl)propane (hydrogenated bisphenol A), glycerin, trimethylolpropane, pentaerythritol, sorbitol, bisphenol A-alkylene oxide Polyglycidyl ether compounds of polyhydric alcohol compounds such as adducts; maleic acid, fumaric acid, itaconic acid, succinic acid, glutaric acid, suberic acid, adipic acid, azelaic acid, sebacic acid, dimer acid, trimer acid, phthalic acid, Glycidyl ester compounds and glycidyl methacrylates of aliphatic, aromatic or alicyclic polybasic acids such as isophthalic acid, terephthalic acid, trimellitic acid, trimesic acid, pyromellitic acid, tetrahydrophthalic acid, endomethylenetetrahydrophthalic acid, etc. Combined or copolymer; N,N-diglycidylaniline, bis(4-(N-methyl-N-glycidylamino)phenyl)methane, diglycidylorthotoluidine, N,N-bis(2,3-epoxypropyl) -4-(2,3-epoxypropoxy)-2-methylaniline, N,N-bis(2,3-epoxypropyl)-4-(2,3-epoxypropoxy)aniline, N,N,N', Epoxy compounds having a glycidylamino group such as N'-tetra(2,3-epoxypropyl)-4,4-diaminodiphenylmethane; vinylcyclohexene diepoxide, cyclopentanediene diepoxide, 3,4-epoxycyclohexylmethyl-3, Epoxidized products of cyclic olefin compounds such as 4-epoxycyclohexanecarboxylate, 3,4-epoxy-6-methylcyclohexylmethyl-6-methylcyclohexanecarboxylate, and bis(3,4-epoxy-6-methylcyclohexylmethyl)adipate; epoxidized conjugated diene polymers such as epoxidized polybutadiene and epoxidized styrene-butadiene copolymers; and heterocyclic compounds such as triglycidyl isocyanurate. In addition, these epoxy resins are those internally crosslinked with a prepolymer having an isocyanate terminal, or those having a high molecular weight with a polyvalent active hydrogen compound (polyhydric phenol, polyamine, carbonyl group-containing compound, polyphosphate ester, etc.). It's okay.
These epoxy resins may be used alone or in combination of two or more.
In the present invention, an epoxy resin having an average of more than 1.1 epoxy groups per molecule is preferred, and an epoxy resin having two or more epoxy groups per molecule is particularly preferred.
前記エポキシ樹脂の中でも、多核多価フェノール化合物のポリグリシジルエーテル化合物、又は多価アルコール化合物のポリグリシジルエーテル化合物の少なくとも一方を含むこと好ましく、多核多価フェノール化合物のポリグリシジルエーテル化合物を含むことがより好ましく、多核多価フェノール化合物のポリグリシジルエーテル化合物を主成分として含むことがさらに好ましく、特にビスフェノール型エポキシ樹脂を主成分として含むことが好ましい。
ここで、主成分とは、エポキシ樹脂中の含有量が５０質量％超であることを意味するものである。
ビスフェノール型エポキシ樹脂とは、ビスフェノールＡ等のビスフェノール類のポリグリシジルエーテル化合物等のビスフェノール構造を有するものをいうものである。
ビスフェノール型エポキシ樹脂を主成分として含有するものが、硬化性及び硬化物の物性に優れたものが得られるため好ましい。
また、本発明の樹脂組成物を繊維強化プラスチックに用いる場合には、繊維材料への浸透性の観点から、２５℃で液状のエポキシ樹脂を使用することが好ましい。 Among the epoxy resins, it preferably contains at least one of a polyglycidyl ether compound of a polynuclear polyhydric phenol compound and a polyglycidyl ether compound of a polyhydric alcohol compound, and more preferably contains a polyglycidyl ether compound of a polynuclear polyhydric phenol compound. It is more preferable to contain a polyglycidyl ether compound of a polynuclear polyhydric phenol compound as a main component, and it is particularly preferable to contain a bisphenol type epoxy resin as a main component.
Here, the main component means that the content in the epoxy resin is more than 50% by mass.
A bisphenol-type epoxy resin is one having a bisphenol structure such as a polyglycidyl ether compound of bisphenols such as bisphenol A.
A resin containing a bisphenol type epoxy resin as a main component is preferable because it provides excellent curability and physical properties of the cured product.
When the resin composition of the present invention is used for fiber-reinforced plastics, it is preferable to use an epoxy resin that is liquid at 25° C. from the viewpoint of permeability into fiber materials.
ここで、主成分とは、エポキシ樹脂中の含有量が５０質量％超であることを意味するものである。
ビスフェノール型エポキシ樹脂とは、ビスフェノールＡ等のビスフェノール類のポリグリシジルエーテル化合物等のビスフェノール構造を有するものをいうものである。
ビスフェノール型エポキシ樹脂を主成分として含有するものが、硬化性及び硬化物の物性に優れたものが得られるため好ましい。
また、本発明の樹脂組成物を繊維強化プラスチックに用いる場合には、繊維材料への浸透性の観点から、２５℃で液状のエポキシ樹脂を使用することが好ましい。 Among the epoxy resins, it preferably contains at least one of a polyglycidyl ether compound of a polynuclear polyhydric phenol compound and a polyglycidyl ether compound of a polyhydric alcohol compound, and more preferably contains a polyglycidyl ether compound of a polynuclear polyhydric phenol compound. It is more preferable to contain a polyglycidyl ether compound of a polynuclear polyhydric phenol compound as a main component, and it is particularly preferable to contain a bisphenol type epoxy resin as a main component.
Here, the main component means that the content in the epoxy resin is more than 50% by mass.
A bisphenol-type epoxy resin is one having a bisphenol structure such as a polyglycidyl ether compound of bisphenols such as bisphenol A.
A resin containing a bisphenol type epoxy resin as a main component is preferable because it provides excellent curability and physical properties of the cured product.
When the resin composition of the present invention is used for fiber-reinforced plastics, it is preferable to use an epoxy resin that is liquid at 25° C. from the viewpoint of permeability into fiber materials.
前記エポキシ樹脂の使用量は、特に限定されるものではないが、繊維強化プラスチック用樹脂組成物１００質量部中、好ましくは１０～９０質量部、より好ましくは１５～８５質量部、さらに好ましくは２０～８０質量部である。
The amount of the epoxy resin used is not particularly limited. ~80 parts by mass.
本発明に使用される（Ｂ）成分であるポリオキシアルキレンポリアミンは、ポリオキシアルキレン骨格を有し、且つアミノ基を２個以上有する化合物であり、分子構造、分子量等に特に制限はない。
The polyoxyalkylene polyamine, which is the component (B) used in the present invention, is a compound having a polyoxyalkylene skeleton and two or more amino groups, and there are no particular restrictions on its molecular structure, molecular weight, and the like.
前記ポリオキシアルキレンポリアミンとしては、例えば、ポリオキシプロピレンジアミン、トリメチロールプロパンポリ（オキシプロピレン）トリアミン、グリセリルポリ（オキシプロピレン）トリアミン、ポリオキシエチレンジアミン、トリメチロールプロパンポリ（オキシエチレン）トリアミン、グリセリルポリ（オキシエチレン）トリアミン等が挙げられる。
Examples of the polyoxyalkylene polyamine include polyoxypropylene diamine, trimethylolpropane poly(oxypropylene)triamine, glycerylpoly(oxypropylene)triamine, polyoxyethylenediamine, trimethylolpropanepoly(oxyethylene)triamine, glycerylpoly( oxyethylene) triamine and the like.
本発明においては、硬化性及び硬化物の物性を向上させる観点から、前記（Ｂ）成分としてポリオキシプロピレンジアミンを使用することが好ましい。
In the present invention, it is preferable to use polyoxypropylenediamine as the component (B) from the viewpoint of improving curability and physical properties of the cured product.
硬化性及び硬化物の物性を向上させる観点から、前記（Ｂ）成分であるポリオキシアルキレンポリアミンの重量平均分子量は、２００～５０００であることが好ましく、２００～２０００であることがより好ましく、特に２００～５００であることが好ましい。
重量平均分子量とは、ゲルパーミエーションクロマトグラフィ（ＧＰＣ）によって測定したポリスチレン換算の重量平均分子量（Ｍｗ）をいうものである。 From the viewpoint of improving the curability and the physical properties of the cured product, the weight average molecular weight of the polyoxyalkylene polyamine which is the component (B) is preferably 200 to 5000, more preferably 200 to 2000, and particularly 200 to 500 is preferred.
The weight average molecular weight refers to the polystyrene equivalent weight average molecular weight (Mw) measured by gel permeation chromatography (GPC).
重量平均分子量とは、ゲルパーミエーションクロマトグラフィ（ＧＰＣ）によって測定したポリスチレン換算の重量平均分子量（Ｍｗ）をいうものである。 From the viewpoint of improving the curability and the physical properties of the cured product, the weight average molecular weight of the polyoxyalkylene polyamine which is the component (B) is preferably 200 to 5000, more preferably 200 to 2000, and particularly 200 to 500 is preferred.
The weight average molecular weight refers to the polystyrene equivalent weight average molecular weight (Mw) measured by gel permeation chromatography (GPC).
前記（Ｂ）成分の市販品としては、例えば、ハンツマン社製のジェファーミンＤ－２３０、ジェファーミンＤ－４００、ジェファーミンＤ－２０００、ジェファーミンＤ－４０００、ジェファーミンＴ－４０３、ジェファーミンＴ－３０００、ジェファーミンＴ－５０００等が挙げられる。
Commercially available products of component (B) include, for example, Huntsman's Jeffamine D-230, Jeffamine D-400, Jeffamine D-2000, Jeffamine D-4000, Jeffamine T-403, and Jeffamine T. -3000, Jeffamine T-5000 and the like.
（Ｂ）成分であるポリオキシアルキレンポリアミンの使用量は、（Ａ）成分であるエポキシ樹脂１００質量部に対し、好ましくは１～５０質量部であり、特に好ましくは５～３０質量部である。（Ｂ）成分であるポリオキシアルキレンポリアミンを１質量部以上使用することで、硬化が十分に進行するようになり、５０質量部以下使用することで、優れた硬化物の物性を得ることができる。
The amount of polyoxyalkylene polyamine used as component (B) is preferably 1 to 50 parts by mass, particularly preferably 5 to 30 parts by mass, per 100 parts by mass of the epoxy resin as component (A). By using 1 part by mass or more of the polyoxyalkylene polyamine as the component (B), curing proceeds sufficiently, and by using 50 parts by mass or less, excellent physical properties of the cured product can be obtained. .
前記（Ｂ）成分であるポリオキシアルキレンポリアミンの使用量は、特に限定されるものではないが、繊維強化プラスチック用樹脂組成物中、好ましくは０．０１～５０質量％、より好ましくは０．０５～４０質量％、特に好ましくは０．１～３０質量％である。
The amount of the polyoxyalkylene polyamine used as the component (B) is not particularly limited, but is preferably 0.01 to 50% by mass, more preferably 0.05%, in the resin composition for fiber-reinforced plastics. to 40% by mass, particularly preferably 0.1 to 30% by mass.
本発明に使用される（Ｃ）成分は下記式（１）で表される化合物であり、（Ａ）成分と（Ｂ）成分の硬化触媒として機能するものである。
The (C) component used in the present invention is a compound represented by the following formula (1) and functions as a curing catalyst for the (A) and (B) components.
（式（１）中、Ｒ１～Ｒ６は、それぞれ独立して、炭素数１～１０の炭化水素基を表し、Ｘ１～Ｘ４はそれぞれ独立して酸素原子又は硫黄原子を表す。）
(In Formula (1), R 1 to R 6 each independently represent a hydrocarbon group having 1 to 10 carbon atoms, and X 1 to X 4 each independently represent an oxygen atom or a sulfur atom.)
前記式（１）中、Ｒ１～Ｒ６で表される炭素数１～１０の炭化水素基としては、例えば、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、第二ブチル基、第三ブチル基、ペンチル基、ヘキシル基、ヘプチル基、オクチル基、イソオクチル基、第三オクチル基、２－エチルヘキシル基、ノニル基、イソノニル基、デシル基、イソデシル基、フェニル基、ベンジル基及びシクロヘキシル基等が挙げられる。これらの中でも、Ｒ１～Ｒ４が、それぞれ独立して、メチル基又はブチル基であることが好ましく、Ｒ５及びＲ６が、それぞれ独立して、メチル基又はエチル基であることが好ましい。硬化性及び非着色性のバランスに優れた樹脂組成物が得られるためである。
In the above formula (1), examples of hydrocarbon groups having 1 to 10 carbon atoms represented by R 1 to R 6 include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, secondary Butyl group, tert-butyl group, pentyl group, hexyl group, heptyl group, octyl group, isooctyl group, tert-octyl group, 2-ethylhexyl group, nonyl group, isononyl group, decyl group, isodecyl group, phenyl group, benzyl group and a cyclohexyl group. Among these, R 1 to R 4 are each independently preferably a methyl group or a butyl group, and R 5 and R 6 are preferably each independently a methyl group or an ethyl group. This is because a resin composition having an excellent balance of curability and non-coloring property can be obtained.
前記（Ｃ）成分である一般式（１）で表される化合物の好ましいものとして、具体的には、下記の一般式（１ａ）又は一般式（１ｂ）で表される化合物等が挙げられる。
Specific examples of preferred compounds represented by the general formula (1) as the component (C) include compounds represented by the following general formula (1a) or general formula (1b).
前記（Ｃ）成分である一般式（１）で表される化合物の配合量は、特に限定されるものではないが、（Ｂ）成分であるポリオキシアルキレンポリアミン１００質量部に対して、０．０１～２０質量部、好ましくは０．０５～１５質量部、特に好ましくは０．１～１０質量部である。（Ｃ）成分である一般式（１）で表される化合物を０．０１質量部以上使用することで、十分な硬化性を得ることができ、２０質量部以下使用することで、十分な貯蔵安定性を得ることができる。
The compounding amount of the compound represented by the general formula (1), which is the component (C), is not particularly limited, but is 0.00 per 100 parts by mass of the polyoxyalkylene polyamine, which is the component (B). 01 to 20 parts by weight, preferably 0.05 to 15 parts by weight, particularly preferably 0.1 to 10 parts by weight. By using 0.01 parts by mass or more of the compound represented by the general formula (1) as component (C), sufficient curability can be obtained, and by using 20 parts by mass or less, sufficient storage can be achieved. Stability can be obtained.
前記（Ｃ）成分である一般式（１）で表される化合物の使用量は、特に限定されるものではないが、繊維強化プラスチック用樹脂組成物中、好ましくは０．００５～１０質量％、より好ましくは０．０１～８質量％、特に好ましくは０．０５～５質量％である。
The amount of the compound represented by the general formula (1), which is the component (C), is not particularly limited, but is preferably 0.005 to 10% by mass in the resin composition for fiber-reinforced plastics, More preferably 0.01 to 8% by mass, particularly preferably 0.05 to 5% by mass.
本発明には、さらに（Ｄ）成分であるシランカップリング剤を含むことが、良好な繊維材料との密着性が得られるため好ましい。前記シランカップリング剤としては、例えば、γ－アミノプロピルトリエトキシシラン、Ｎ－β－（アミノエチル）－γ－アミノプロピルトリエトキシシラン、Ｎ－β－（アミノエチル）－Ｎ’－β－（アミノエチル）－γ－アミノプロピルトリエトキシシラン、γ－アニリノプロピルトリエトキシシラン、γ－グリシドキシプロピルトリエトキシシラン、β－（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、ビニルトリエトキシシラン、Ｎ－β－（Ｎ－ビニルベンジルアミノエチル）－γ－アミノプロピルトリエトキシシラン、γ－メタクリロキシプロピルトリメトキシシラン、γ－クロロプロピルトリメトキシシラン、γ－メルカプトプロピルトリメトキシシラン、γ－イソシアネートプロピルトリエトキシシラン等のシランカップリング剤；イソプロピルトリイソステアロイルチタネート、イソプロピルトリ－ｎ－ドデシルベンゼンスルホニルチタネート、イソプロピルトリス（ジオクチルピロホスフェート）チタネート、テトライソプロピルビス（ジオクチルホスファイト）チタネート、テトラオクチルビス（ジトリデシルホスファイト）チタネート、テトラ（２，２－ジアリルオキシメチル－１－ブチル）ビス（ジ－トリデシル）ホスファイトチタネート、ビス（ジオクチルピロホスフェート）オキシアセテートチタネート、ビス（ジオクチルピロホスフェート）エチレンチタネート、イソプロピルトリオクタノイルチタネート、イソプロピルジメタクリロイルイソステアロイルチタネート、イソプロピルイソステアロイルジアクリルチタネート、イソプロピルトリ（ジオクチルホスフェート）チタネート、イソプロピルトリクミルフェニルチタネート、イソプロピルトリ（Ｎ－アミノエチル－アミノエチル）チタネート、テトライソプロピルチタネート、テトラノルマルブチルチタネート、ブチルチタネートダイマー、テトラキス（２－エチルヘキシル）チタネート、テトラステアリルチタネート、テトラメチルチタネート、ジエトキシビス（アセチルアセトナト）チタン、ジイソプロピルビス（アセチルアセトナト）チタン、ジイソプロポキシビス（エチルアセトアセテート）チタン、イソプロポキシ（２－エチル－１，３－ヘキサンジオラト）チタン、ジ（２－エチルヘキソキシ）ビス（２－エチル－１，３－ヘキサンジオラト）チタン、ジ－ｎ－ブトキシビス（トリエタノールアミナト）チタン、テトラアセチルアセトネートチタン、ヒドロキシビス（ラクタト）チタン、ジクミルフェニルオキシアセテートチタネート、ジイソステアロイルエチレンチタネート等のチタンカップリング剤；ジルコニウムトリブトキシステアレート、テトラ（２，２－ジアリルオキシメチル）ブチルジ（ジトリデシル）ホスフィトジルコネート、ネオペンチル（ジアリル）オキシトリネオデカノイルジルコネート、ネオペンチル（ジアリル）オキシトリ（ドデシル）ベンゼン－スルホニルジルコネート、ネオペンチル（ジアリル）オキシトリ（ジオクチル）ホスファトジルコネート、ネオペンチル（ジアリル）オキシトリ（ジオクチル）ピロ－ホスファトジルコネート、ネオペンチル（ジアリル）オキシトリ（Ｎ－エチレンジアミノ）エチルジルコネート、ネオペンチル（ジアリル）オキシトリ（ｍ－アミノ）フェニルジルコネート、ネオペンチル（ジアリル）オキシトリメタクリルジルコネート、ネオペンチル（ジアリル）オキシトリアクリルジルコネート、ジネオペンチル（ジアリル）オキシジパラアミノベンゾイルジルコネート、ジネオペンチル（ジアリル）オキシジ（３－メルカプト）プロピルジルコネート、テトラノルマルプロポキシジルコニウム、テトラノルマルブトキシジルコニウム、ジルコニウム２，２－ビス（２－プロペノラトメチル）ブチラート，ジルコニウムテトラアセチルアセトネート、ジルコニウムトリブトキシアセチルアセトネート、ジルコニウムジブトキシビス（アセチルアセトネート）、ジルコニウムジブトキシビス（アセチルアセトネート）、ジルコニウムトリブトキシエチルアセトアセテート、ジルコニウムモノブトキシアセチルアセトネートビス（エチルアセトアセテート）等のジルコニウム系カップリング剤等が挙げられる。
前記シランカップリング剤の中でも、入手が容易で安価であるという点で、γ－アミノプロピルトリメトキシシラン、及び／又はγ－グリシドキシプロピルトリメトキシシランを添加することがより好ましく、γ－グリシドキシプロピルトリメトキシシランを添加することが最も好ましい。 It is preferable that the present invention further contains a silane coupling agent as the component (D) because good adhesion to the fiber material can be obtained. Examples of the silane coupling agent include γ-aminopropyltriethoxysilane, N-β-(aminoethyl)-γ-aminopropyltriethoxysilane, N-β-(aminoethyl)-N'-β-( aminoethyl)-γ-aminopropyltriethoxysilane, γ-anilinopropyltriethoxysilane, γ-glycidoxypropyltriethoxysilane, β-(3,4-epoxycyclohexyl)ethyltriethoxysilane, vinyltriethoxysilane , N-β-(N-vinylbenzylaminoethyl)-γ-aminopropyltriethoxysilane, γ-methacryloxypropyltrimethoxysilane, γ-chloropropyltrimethoxysilane, γ-mercaptopropyltrimethoxysilane, γ-isocyanate Silane coupling agents such as propyl triethoxysilane; ditridecylphosphite) titanate, tetra(2,2-diallyloxymethyl-1-butyl)bis(di-tridecyl)phosphite titanate, bis(dioctylpyrophosphate)oxyacetate titanate, bis(dioctylpyrophosphate)ethylene titanate, Isopropyl trioctanoyl titanate, isopropyl dimethacryloyl isostearoyl titanate, isopropyl isostearoyl diacryl titanate, isopropyl tri(dioctylphosphate) titanate, isopropyl tricumylphenyl titanate, isopropyl tri(N-aminoethyl-aminoethyl) titanate, tetraisopropyl titanate , tetra-n-butyl titanate, butyl titanate dimer, tetrakis(2-ethylhexyl) titanate, tetrastearyl titanate, tetramethyl titanate, diethoxybis(acetylacetonato)titanium, diisopropylbis(acetylacetonato)titanium, diisopropylbis(ethylacetonate) Acetate) titanium, isopropoxy(2-ethyl-1,3-hexanediolato) titanium, di(2-ethylhexoxy)bis(2-ethyl-1,3-hexanediolato)titanium, di-n-butoxybis(tri titanium coupling agents such as ethanol aminato) titanium, tetraacetylacetonate titanium, hydroxybis(lactato) titanium, dicumylphenyloxyacetate titanate, diisostearoylethylene titanate; zirconium tributoxysterate, tetra(2,2- diallyloxymethyl)butyl di(ditridecyl)phosphitozirconate, neopentyl(diallyl)oxytri-neodecanoyl zirconate, neopentyl(diallyl)oxytri(dodecyl)benzene-sulfonylzirconate, neopentyl(diallyl)oxytri(dioctyl)phosphatozirconate neopentyl(diallyl)oxytri(dioctyl)pyro-phosphatozirconate, neopentyl(diallyl)oxytri(N-ethylenediamino)ethylzirconate, neopentyl(diallyl)oxytri(m-amino)phenylzirconate, neopentyl(diallyl) Oxytrimethacryl zirconate, neopentyl (diallyl) oxytriacryl zirconate, dineopentyl (diallyl) oxydi-para-aminobenzoyl zirconate, dineopentyl (diallyl) oxydi(3-mercapto)propyl zirconate, tetra-normal propoxy zirconium, tetra-normal butoxy zirconium , zirconium 2,2-bis(2-propenolatomethyl)butyrate, zirconium tetraacetylacetonate, zirconium tributoxyacetylacetonate, zirconium dibutoxybis(acetylacetonate), zirconium dibutoxybis(acetylacetonate), Zirconium coupling agents such as zirconium tributoxyethylacetoacetate, zirconium monobutoxyacetylacetonate bis(ethylacetoacetate), and the like.
Among the silane coupling agents, γ-aminopropyltrimethoxysilane and/or γ-glycidoxypropyltrimethoxysilane are more preferably added because they are readily available and inexpensive. Most preferably, sidoxypropyltrimethoxysilane is added.
前記シランカップリング剤の中でも、入手が容易で安価であるという点で、γ－アミノプロピルトリメトキシシラン、及び／又はγ－グリシドキシプロピルトリメトキシシランを添加することがより好ましく、γ－グリシドキシプロピルトリメトキシシランを添加することが最も好ましい。 It is preferable that the present invention further contains a silane coupling agent as the component (D) because good adhesion to the fiber material can be obtained. Examples of the silane coupling agent include γ-aminopropyltriethoxysilane, N-β-(aminoethyl)-γ-aminopropyltriethoxysilane, N-β-(aminoethyl)-N'-β-( aminoethyl)-γ-aminopropyltriethoxysilane, γ-anilinopropyltriethoxysilane, γ-glycidoxypropyltriethoxysilane, β-(3,4-epoxycyclohexyl)ethyltriethoxysilane, vinyltriethoxysilane , N-β-(N-vinylbenzylaminoethyl)-γ-aminopropyltriethoxysilane, γ-methacryloxypropyltrimethoxysilane, γ-chloropropyltrimethoxysilane, γ-mercaptopropyltrimethoxysilane, γ-isocyanate Silane coupling agents such as propyl triethoxysilane; ditridecylphosphite) titanate, tetra(2,2-diallyloxymethyl-1-butyl)bis(di-tridecyl)phosphite titanate, bis(dioctylpyrophosphate)oxyacetate titanate, bis(dioctylpyrophosphate)ethylene titanate, Isopropyl trioctanoyl titanate, isopropyl dimethacryloyl isostearoyl titanate, isopropyl isostearoyl diacryl titanate, isopropyl tri(dioctylphosphate) titanate, isopropyl tricumylphenyl titanate, isopropyl tri(N-aminoethyl-aminoethyl) titanate, tetraisopropyl titanate , tetra-n-butyl titanate, butyl titanate dimer, tetrakis(2-ethylhexyl) titanate, tetrastearyl titanate, tetramethyl titanate, diethoxybis(acetylacetonato)titanium, diisopropylbis(acetylacetonato)titanium, diisopropylbis(ethylacetonate) Acetate) titanium, isopropoxy(2-ethyl-1,3-hexanediolato) titanium, di(2-ethylhexoxy)bis(2-ethyl-1,3-hexanediolato)titanium, di-n-butoxybis(tri titanium coupling agents such as ethanol aminato) titanium, tetraacetylacetonate titanium, hydroxybis(lactato) titanium, dicumylphenyloxyacetate titanate, diisostearoylethylene titanate; zirconium tributoxysterate, tetra(2,2- diallyloxymethyl)butyl di(ditridecyl)phosphitozirconate, neopentyl(diallyl)oxytri-neodecanoyl zirconate, neopentyl(diallyl)oxytri(dodecyl)benzene-sulfonylzirconate, neopentyl(diallyl)oxytri(dioctyl)phosphatozirconate neopentyl(diallyl)oxytri(dioctyl)pyro-phosphatozirconate, neopentyl(diallyl)oxytri(N-ethylenediamino)ethylzirconate, neopentyl(diallyl)oxytri(m-amino)phenylzirconate, neopentyl(diallyl) Oxytrimethacryl zirconate, neopentyl (diallyl) oxytriacryl zirconate, dineopentyl (diallyl) oxydi-para-aminobenzoyl zirconate, dineopentyl (diallyl) oxydi(3-mercapto)propyl zirconate, tetra-normal propoxy zirconium, tetra-normal butoxy zirconium , zirconium 2,2-bis(2-propenolatomethyl)butyrate, zirconium tetraacetylacetonate, zirconium tributoxyacetylacetonate, zirconium dibutoxybis(acetylacetonate), zirconium dibutoxybis(acetylacetonate), Zirconium coupling agents such as zirconium tributoxyethylacetoacetate, zirconium monobutoxyacetylacetonate bis(ethylacetoacetate), and the like.
Among the silane coupling agents, γ-aminopropyltrimethoxysilane and/or γ-glycidoxypropyltrimethoxysilane are more preferably added because they are readily available and inexpensive. Most preferably, sidoxypropyltrimethoxysilane is added.
（Ｄ）成分であるシランカップリング剤の配合量は、特に限定されるものではないが、前記（Ａ）成分であるエポキシ樹脂の総量１００質量部に対し、０．１～５０質量部であることが好ましい。樹脂との混和性が良好であり、繊維との密着性が向上するという観点から、０．５～３０質量部、特に１～２０質量部配合させることが特に好ましい。
The amount of the silane coupling agent, component (D), is not particularly limited, but is 0.1 to 50 parts by mass with respect to 100 parts by mass of the epoxy resin, component (A). is preferred. From the viewpoint of good miscibility with the resin and improved adhesion to the fiber, it is particularly preferable to add 0.5 to 30 parts by mass, particularly 1 to 20 parts by mass.
前記（Ｄ）成分であるシランカップリング剤の使用量は、特に限定されるものではないが、繊維強化プラスチック用樹脂組成物中、好ましくは０．００５～１０質量％、より好ましくは０．０１～８質量％、特に好ましくは０．０５～５質量％である。
The amount of the silane coupling agent used as the component (D) is not particularly limited, but is preferably 0.005 to 10% by mass, more preferably 0.01%, in the resin composition for fiber-reinforced plastics. to 8% by weight, particularly preferably 0.05 to 5% by weight.
本発明においては、所望の粘度に調整して使用するために、（Ｅ）成分である反応性希釈剤を併用してもよい。前記反応性希釈剤は、樹脂組成物の硬化後に硬化物中に取り込まれることで硬化物物性に影響を与えないものである。エポキシ樹脂組成物用の反応性希釈剤としては、分子中にエポキシ基を有する希釈剤があげられる。このような反応性希釈剤としては、例えば、ｎ－ブチルグリシジルエーテル、Ｃ１２～Ｃ１４のアルキルグリシジルエーテル、アリルグリシジルエーテル、２－エチルヘキシルグリシジルエーテル、スチレンオキシド、フェニルグリシジルエーテル、クレジルグリシジルエーテル、ｐ－ｓｅｃ－ブチルフェニルグリシジルエーテル、ｔ－ブチルフェニルグリシジルエーテル、グリシジルメタクリレート、及び３級カルボン酸グリシジルエステル等のモノグリシジルエーテル化合物などが挙げられる。
In the present invention, a reactive diluent as component (E) may be used in combination in order to adjust the viscosity to a desired level. The reactive diluent is incorporated into the cured product after the resin composition is cured, so that it does not affect the physical properties of the cured product. Reactive diluents for epoxy resin compositions include diluents having an epoxy group in the molecule. Examples of such reactive diluents include n-butyl glycidyl ether, C 12 -C 14 alkyl glycidyl ether, allyl glycidyl ether, 2-ethylhexyl glycidyl ether, styrene oxide, phenyl glycidyl ether, cresyl glycidyl ether, Examples include monoglycidyl ether compounds such as p-sec-butylphenyl glycidyl ether, t-butylphenyl glycidyl ether, glycidyl methacrylate, and tertiary carboxylic acid glycidyl esters.
本発明の繊維強化プラスチック用樹脂組成物には、必要に応じて、更に添加剤を併用してもよい。上記添加剤としては、例えば、ジオクチルフタレート、ジブチルフタレート、ベンジルアルコール、コールタール等の非反応性の希釈剤（可塑剤）；顔料；キャンデリラワックス、カルナウバワックス、木ろう、イボタロウ、みつろう、ラノリン、鯨ろう、モンタンワックス、石油ワックス、脂肪酸ワックス、脂肪酸エステル、脂肪酸エーテル、芳香族エステル、芳香族エーテル等の潤滑剤；増粘剤；チキソトロピック剤；酸化防止剤；光安定剤；紫外線吸収剤；難燃剤；消泡剤；防錆剤等の常用の添加剤を挙げることができる。
Additives may be used in combination with the resin composition for fiber-reinforced plastics of the present invention, if necessary. Examples of the above additives include non-reactive diluents (plasticizers) such as dioctyl phthalate, dibutyl phthalate, benzyl alcohol and coal tar; pigments; candelilla wax, carnauba wax, Japan wax, ivory wax, beeswax, lanolin , spermaceti, montan wax, petroleum wax, fatty acid wax, fatty acid ester, fatty acid ether, aromatic ester, lubricant such as aromatic ether; thickener; thixotropic agent; antioxidant; light stabilizer; ultraviolet absorber ;flame retardants; antifoaming agents;
本発明の繊維強化プラスチック用樹脂組成物は、繊維強化プラスチックに使用されることから、２５℃で液状であることが好ましく、特に、その粘度が１００～３０００Ｐａ・ｓであることが好ましい。
Since the resin composition for fiber-reinforced plastics of the present invention is used for fiber-reinforced plastics, it is preferably liquid at 25°C, and particularly preferably has a viscosity of 100 to 3000 Pa·s.
本発明の繊維強化プラスチック用樹脂組成物は、炭素繊維、ガラス繊維等を強化繊維とする繊維強化プラスチックのマトリックス樹脂として好適である。強化繊維の種類は特に限定されず、例えば炭素繊維、ガラス繊維、アラミド繊維、ボロン繊維、アルミナ繊維、シリコーンカーバイド繊維等を単独で用いてもよいし、２種類以上のハイブリッド繊維として用いてもよい。
The resin composition for fiber-reinforced plastics of the present invention is suitable as a matrix resin for fiber-reinforced plastics having reinforcing fibers such as carbon fiber and glass fiber. The type of reinforcing fiber is not particularly limited, and for example, carbon fiber, glass fiber, aramid fiber, boron fiber, alumina fiber, silicone carbide fiber, etc. may be used alone, or two or more types of hybrid fibers may be used. .
上記した強化繊維の形態としては、高強度・高弾性率繊維を一方向に配列させたいわゆるトウシートや、前記繊維糸状を一方向又は二方向に配列させた一方向性織物や二方向性織物、三方向に配列させた三軸織物、多方向に配列させた多軸織物等が挙げられる。トウシートにおいては、基材への樹脂含浸性を向上させるために、ストランド間に適度な隙間を確保するように前記繊維を配列するとよい。
Examples of the form of the reinforcing fibers include so-called tow sheets in which high-strength, high-modulus fibers are arranged in one direction, unidirectional or bidirectional fabrics in which the fiber threads are arranged in one or two directions, Examples include triaxial woven fabrics arranged in three directions and multiaxial woven fabrics arranged in multiple directions. In the tow sheet, the fibers are preferably arranged so as to secure an appropriate gap between the strands in order to improve the resin impregnation property of the base material.
本発明の繊維強化プラスチック用樹脂組成物を使用した繊維強化プラスチックを成形するための方法は、特に限定されるものではないが、例えば、押し出し成形法、ブロー成形法、圧縮成形法、真空成形法、射出成形法、ＲＴＭ（Ｒｅｓｉｎ Ｔｒａｎｓｆｅｒ Ｍｏｌｄｉｎｇ）成形、ＶａＲＴＭ（Ｖａｃｃｕｍ ａｓｓｉｓｔ Ｒｅｓｉｎ Ｔｒａｎｓｆｅｒ Ｍｏｌｄｉｎｇ）成形、積層成形、ハンドレイアップ成形、フィラメントワインディング成型等が挙げられる。
The method for molding fiber-reinforced plastics using the resin composition for fiber-reinforced plastics of the present invention is not particularly limited, but examples thereof include extrusion molding, blow molding, compression molding, and vacuum molding. , injection molding, RTM (resin transfer molding) molding, VaRTM (vacuum assist resin transfer molding) molding, laminate molding, hand lay-up molding, filament winding molding, and the like.
繊維強化プラスチックに含まれる繊維強化プラスチック用樹脂組成物の硬化物の量は、好ましくは５～９５質量％、特に好ましくは１０～８０質量％、さらに好ましくは２０～７０質量％であり、この範囲で使用されることにより優れた物性を示すことができるため好ましい。
The amount of the cured product of the resin composition for fiber-reinforced plastic contained in the fiber-reinforced plastic is preferably 5 to 95% by mass, particularly preferably 10 to 80% by mass, further preferably 20 to 70% by mass. It is preferable because it can exhibit excellent physical properties by being used in.
本発明の繊維強化プラスチック用樹脂組成物を用いて得られる繊維強化プラスチックは、各種の用途に利用することができる。例えば、自動車、船舶及び鉄道車両等の移動体の構造材、ドライブシャフト、板バネ、風車ブレード、圧力容器、フライホイール、製紙用ローラー、屋根材、ケーブル、及び補修補強材料等の一般産業用途；胴体、主翼、尾翼、動翼、フェアリング、カウル、ドア、座席、内装材、モーターケース、アンテナ等の航空宇宙用途；ゴルフシャフト、釣り竿、テニスやバドミントンのラケット用途、ホッケー等のスティック用途、及びスキーポール用途等のスポーツ用途が挙げられる。
The fiber-reinforced plastic obtained using the resin composition for fiber-reinforced plastic of the present invention can be used for various purposes. For example, general industrial applications such as structural materials for moving bodies such as automobiles, ships and railway vehicles, drive shafts, leaf springs, windmill blades, pressure vessels, flywheels, papermaking rollers, roofing materials, cables, and repair and reinforcement materials; Aerospace applications such as fuselages, main wings, tail wings, rotor blades, fairings, cowls, doors, seats, interior materials, motor cases, antennas; golf shafts, fishing rods, tennis and badminton rackets, hockey sticks, and so on. Sports applications such as ski pole applications.
以下本発明を、実施例に基づいて更に具体的に説明する。
The present invention will be described more specifically below based on examples.
［実施例１］
５００ｍＬディスポカップに、アデカレジンＥＰ－４１００Ｅ（（株）ＡＤＥＫＡ製；ビスフェノールＡ型エポキシ樹脂、エポキシ当量：１９０ｇ／ｅｑ．）を９８．６ｇ、ジェファーミンＤ－２３０（ハンツマン社製；ポリプロピレンポリアミン）を３２ｇ、ヒシコーリンＰＸ－４ＥＴ（日本化学工業製；テトラブチルホスホニウム Ｏ，Ｏ－ジエチルホスホロジチオエート）を２ｇ及びＫＢＭ－４０３（信越化学工業（株）製、γ－グリシドキシプロピルトリメトキシシラン）を１．４ｇ加え、２５℃にて５分間スパチュラで撹拌した。その後、遊星式攪拌機を使用して更に撹拌し、樹脂組成物を得た。 [Example 1]
In a 500 mL disposable cup, 98.6 g of ADEKA RESIN EP-4100E (manufactured by ADEKA Co., Ltd.; bisphenol A type epoxy resin, epoxy equivalent: 190 g / eq.), 32 g of Jeffamine D-230 (manufactured by Huntsman; polypropylene polyamine) , 2 g of hishicolin PX-4ET (manufactured by Nippon Kagaku Kogyo; tetrabutylphosphonium O,O-diethylphosphorodithioate) and KBM-403 (manufactured by Shin-Etsu Chemical Co., Ltd., γ-glycidoxypropyltrimethoxysilane) 1.4 g was added and stirred with a spatula for 5 minutes at 25°C. Thereafter, the mixture was further stirred using a planetary stirrer to obtain a resin composition.
５００ｍＬディスポカップに、アデカレジンＥＰ－４１００Ｅ（（株）ＡＤＥＫＡ製；ビスフェノールＡ型エポキシ樹脂、エポキシ当量：１９０ｇ／ｅｑ．）を９８．６ｇ、ジェファーミンＤ－２３０（ハンツマン社製；ポリプロピレンポリアミン）を３２ｇ、ヒシコーリンＰＸ－４ＥＴ（日本化学工業製；テトラブチルホスホニウム Ｏ，Ｏ－ジエチルホスホロジチオエート）を２ｇ及びＫＢＭ－４０３（信越化学工業（株）製、γ－グリシドキシプロピルトリメトキシシラン）を１．４ｇ加え、２５℃にて５分間スパチュラで撹拌した。その後、遊星式攪拌機を使用して更に撹拌し、樹脂組成物を得た。 [Example 1]
In a 500 mL disposable cup, 98.6 g of ADEKA RESIN EP-4100E (manufactured by ADEKA Co., Ltd.; bisphenol A type epoxy resin, epoxy equivalent: 190 g / eq.), 32 g of Jeffamine D-230 (manufactured by Huntsman; polypropylene polyamine) , 2 g of hishicolin PX-4ET (manufactured by Nippon Kagaku Kogyo; tetrabutylphosphonium O,O-diethylphosphorodithioate) and KBM-403 (manufactured by Shin-Etsu Chemical Co., Ltd., γ-glycidoxypropyltrimethoxysilane) 1.4 g was added and stirred with a spatula for 5 minutes at 25°C. Thereafter, the mixture was further stirred using a planetary stirrer to obtain a resin composition.
［実施例２］
５００ｍＬディスポカップに、アデカレジンＥＰ－４１００Ｅ（（株）ＡＤＥＫＡ製；ビスフェノールＡ型エポキシ樹脂、エポキシ当量：１９０ｇ／ｅｑ．）を８３．９ｇ、アデカグリシロールＥＤ－５２３Ｔ（（株）ＡＤＥＫＡ製；ネオペンチルグリコール型エポキシ樹脂：エポキシ当量１４０ｇ／ｅｑ．）を１４．８ｇ、ジェファーミンＤ－２３０（ハンツマン社製；ポリプロピレンポリアミン）を３２ｇ、ヒシコーリンＰＸ－４ＥＴ（日本化学工業製；テトラブチルホスホニウム Ｏ，Ｏ－ジエチルホスホロジチオエート）を２ｇ及びＫＢＭ－４０３（信越化学工業（株）製、γ－グリシドキシプロピルトリメトキシシラン）を１．３ｇ加え、２５℃にて５分間スパチュラで撹拌した。その後、遊星式攪拌機を使用して更に撹拌し、樹脂組成物を得た。 [Example 2]
In a 500 mL disposable cup, 83.9 g of ADEKA RESIN EP-4100E (manufactured by ADEKA Corporation; bisphenol A type epoxy resin, epoxy equivalent: 190 g / eq.), ADEKA GLYCIROL ED-523T (manufactured by ADEKA Corporation; neopentyl Glycol-type epoxy resin: 14.8 g of epoxy equivalent 140 g / eq.), 32 g of Jeffamine D-230 (manufactured by Huntsman; polypropylene polyamine), Hishikorin PX-4ET (manufactured by Nippon Kagaku Kogyo; tetrabutylphosphonium O, O- 2 g of diethyl phosphorodithioate) and 1.3 g of KBM-403 (manufactured by Shin-Etsu Chemical Co., Ltd., γ-glycidoxypropyltrimethoxysilane) were added and stirred with a spatula at 25° C. for 5 minutes. Thereafter, the mixture was further stirred using a planetary stirrer to obtain a resin composition.
５００ｍＬディスポカップに、アデカレジンＥＰ－４１００Ｅ（（株）ＡＤＥＫＡ製；ビスフェノールＡ型エポキシ樹脂、エポキシ当量：１９０ｇ／ｅｑ．）を８３．９ｇ、アデカグリシロールＥＤ－５２３Ｔ（（株）ＡＤＥＫＡ製；ネオペンチルグリコール型エポキシ樹脂：エポキシ当量１４０ｇ／ｅｑ．）を１４．８ｇ、ジェファーミンＤ－２３０（ハンツマン社製；ポリプロピレンポリアミン）を３２ｇ、ヒシコーリンＰＸ－４ＥＴ（日本化学工業製；テトラブチルホスホニウム Ｏ，Ｏ－ジエチルホスホロジチオエート）を２ｇ及びＫＢＭ－４０３（信越化学工業（株）製、γ－グリシドキシプロピルトリメトキシシラン）を１．３ｇ加え、２５℃にて５分間スパチュラで撹拌した。その後、遊星式攪拌機を使用して更に撹拌し、樹脂組成物を得た。 [Example 2]
In a 500 mL disposable cup, 83.9 g of ADEKA RESIN EP-4100E (manufactured by ADEKA Corporation; bisphenol A type epoxy resin, epoxy equivalent: 190 g / eq.), ADEKA GLYCIROL ED-523T (manufactured by ADEKA Corporation; neopentyl Glycol-type epoxy resin: 14.8 g of epoxy equivalent 140 g / eq.), 32 g of Jeffamine D-230 (manufactured by Huntsman; polypropylene polyamine), Hishikorin PX-4ET (manufactured by Nippon Kagaku Kogyo; tetrabutylphosphonium O, O- 2 g of diethyl phosphorodithioate) and 1.3 g of KBM-403 (manufactured by Shin-Etsu Chemical Co., Ltd., γ-glycidoxypropyltrimethoxysilane) were added and stirred with a spatula at 25° C. for 5 minutes. Thereafter, the mixture was further stirred using a planetary stirrer to obtain a resin composition.
［実施例３］
５００ｍＬディスポカップに、アデカレジンＥＰ－４１００Ｅ（（株）ＡＤＥＫＡ製；ビスフェノールＡ型エポキシ樹脂、エポキシ当量：１９０ｇ／ｅｑ．）を７９．０ｇ、ジェファーミンＤ－２３０（ハンツマン社製；ポリプロピレンポリアミン）を３０．６ｇ、ヒシコーリンＰＸ－４ＥＴ（日本化学工業製；テトラブチルホスホニウム Ｏ，Ｏ－ジエチルホスホロジチオエート）を２ｇ、ＫＢＭ－４０３（信越化学工業（株）製、γ－グリシドキシプロピルトリメトキシシラン）を１．２ｇ及びアデカグリシロールＥＤ－５０９Ｅ（（株）ＡＤＥＫＡ製；ｔ－ブチルフェニルグリシジルエーテル：エポキシ当量２１０ｇ／ｅｑ．）を１９．８ｇ加え、２５℃にて５分間スパチュラで撹拌した。その後、遊星式攪拌機を使用して更に撹拌し、樹脂組成物を得た。 [Example 3]
79.0 g of ADEKA RESIN EP-4100E (manufactured by ADEKA Corporation; bisphenol A type epoxy resin, epoxy equivalent: 190 g/eq.) and 30 of Jeffamine D-230 (manufactured by Huntsman; polypropylene polyamine) are placed in a 500 mL disposable cup. 6 g, Hishikorin PX-4ET (manufactured by Nippon Kagaku Kogyo; tetrabutylphosphonium O,O-diethylphosphorodithioate) 2 g, KBM-403 (manufactured by Shin-Etsu Chemical Co., Ltd., γ-glycidoxypropyltrimethoxysilane ) and 19.8 g of ADEKA GLYCIROL ED-509E (manufactured by ADEKA; t-butylphenylglycidyl ether: epoxy equivalent: 210 g/eq.) were added and stirred with a spatula at 25° C. for 5 minutes. Thereafter, the mixture was further stirred using a planetary stirrer to obtain a resin composition.
５００ｍＬディスポカップに、アデカレジンＥＰ－４１００Ｅ（（株）ＡＤＥＫＡ製；ビスフェノールＡ型エポキシ樹脂、エポキシ当量：１９０ｇ／ｅｑ．）を７９．０ｇ、ジェファーミンＤ－２３０（ハンツマン社製；ポリプロピレンポリアミン）を３０．６ｇ、ヒシコーリンＰＸ－４ＥＴ（日本化学工業製；テトラブチルホスホニウム Ｏ，Ｏ－ジエチルホスホロジチオエート）を２ｇ、ＫＢＭ－４０３（信越化学工業（株）製、γ－グリシドキシプロピルトリメトキシシラン）を１．２ｇ及びアデカグリシロールＥＤ－５０９Ｅ（（株）ＡＤＥＫＡ製；ｔ－ブチルフェニルグリシジルエーテル：エポキシ当量２１０ｇ／ｅｑ．）を１９．８ｇ加え、２５℃にて５分間スパチュラで撹拌した。その後、遊星式攪拌機を使用して更に撹拌し、樹脂組成物を得た。 [Example 3]
79.0 g of ADEKA RESIN EP-4100E (manufactured by ADEKA Corporation; bisphenol A type epoxy resin, epoxy equivalent: 190 g/eq.) and 30 of Jeffamine D-230 (manufactured by Huntsman; polypropylene polyamine) are placed in a 500 mL disposable cup. 6 g, Hishikorin PX-4ET (manufactured by Nippon Kagaku Kogyo; tetrabutylphosphonium O,O-diethylphosphorodithioate) 2 g, KBM-403 (manufactured by Shin-Etsu Chemical Co., Ltd., γ-glycidoxypropyltrimethoxysilane ) and 19.8 g of ADEKA GLYCIROL ED-509E (manufactured by ADEKA; t-butylphenylglycidyl ether: epoxy equivalent: 210 g/eq.) were added and stirred with a spatula at 25° C. for 5 minutes. Thereafter, the mixture was further stirred using a planetary stirrer to obtain a resin composition.
［実施例４］
５００ｍＬディスポカップに、アデカレジンＥＰ－４１００Ｅ（（株）ＡＤＥＫＡ製；ビスフェノールＡ型エポキシ樹脂、エポキシ当量：１９０ｇ／ｅｑ．）を７４．０ｇ、ジェファーミンＤ－２３０（ハンツマン社製；ポリプロピレンポリアミン）を３０．６ｇ、ヒシコーリンＰＸ－４ＥＴ（日本化学工業製；テトラブチルホスホニウム Ｏ，Ｏ－ジエチルホスホロジチオエート）を２ｇ、ＫＢＭ－４０３（信越化学工業（株）製、γ－グリシドキシプロピルトリメトキシシラン）を１．２ｇ及びアデカグリシロールＥＤ－５０９Ｅ（（株）ＡＤＥＫＡ製；ｔ－ブチルフェニルグリシジルエーテル：エポキシ当量２１０ｇ／ｅｑ．）を２４．８ｇ加え、２５℃にて５分間スパチュラで撹拌した。その後、遊星式攪拌機を使用して更に撹拌し、樹脂組成物を得た。 [Example 4]
In a 500 mL disposable cup, 74.0 g of ADEKA RESIN EP-4100E (manufactured by ADEKA Co., Ltd.; bisphenol A type epoxy resin, epoxy equivalent: 190 g / eq.), 30 of Jeffamine D-230 (manufactured by Huntsman; polypropylene polyamine) 6 g, Hishikorin PX-4ET (manufactured by Nippon Kagaku Kogyo; tetrabutylphosphonium O,O-diethylphosphorodithioate) 2 g, KBM-403 (manufactured by Shin-Etsu Chemical Co., Ltd., γ-glycidoxypropyltrimethoxysilane ) and 24.8 g of ADEKA GLYCIROL ED-509E (manufactured by ADEKA; t-butylphenylglycidyl ether: epoxy equivalent: 210 g/eq.) were added and stirred with a spatula at 25° C. for 5 minutes. Thereafter, the mixture was further stirred using a planetary stirrer to obtain a resin composition.
５００ｍＬディスポカップに、アデカレジンＥＰ－４１００Ｅ（（株）ＡＤＥＫＡ製；ビスフェノールＡ型エポキシ樹脂、エポキシ当量：１９０ｇ／ｅｑ．）を７４．０ｇ、ジェファーミンＤ－２３０（ハンツマン社製；ポリプロピレンポリアミン）を３０．６ｇ、ヒシコーリンＰＸ－４ＥＴ（日本化学工業製；テトラブチルホスホニウム Ｏ，Ｏ－ジエチルホスホロジチオエート）を２ｇ、ＫＢＭ－４０３（信越化学工業（株）製、γ－グリシドキシプロピルトリメトキシシラン）を１．２ｇ及びアデカグリシロールＥＤ－５０９Ｅ（（株）ＡＤＥＫＡ製；ｔ－ブチルフェニルグリシジルエーテル：エポキシ当量２１０ｇ／ｅｑ．）を２４．８ｇ加え、２５℃にて５分間スパチュラで撹拌した。その後、遊星式攪拌機を使用して更に撹拌し、樹脂組成物を得た。 [Example 4]
In a 500 mL disposable cup, 74.0 g of ADEKA RESIN EP-4100E (manufactured by ADEKA Co., Ltd.; bisphenol A type epoxy resin, epoxy equivalent: 190 g / eq.), 30 of Jeffamine D-230 (manufactured by Huntsman; polypropylene polyamine) 6 g, Hishikorin PX-4ET (manufactured by Nippon Kagaku Kogyo; tetrabutylphosphonium O,O-diethylphosphorodithioate) 2 g, KBM-403 (manufactured by Shin-Etsu Chemical Co., Ltd., γ-glycidoxypropyltrimethoxysilane ) and 24.8 g of ADEKA GLYCIROL ED-509E (manufactured by ADEKA; t-butylphenylglycidyl ether: epoxy equivalent: 210 g/eq.) were added and stirred with a spatula at 25° C. for 5 minutes. Thereafter, the mixture was further stirred using a planetary stirrer to obtain a resin composition.
［比較例１］
ヒシコーリンＰＸ－４ＥＴに変えて２－エチル－４－メチルイミダゾールを２ｇ用いた以外は実施例２と同様にして樹脂組成物を得た。 [Comparative Example 1]
A resin composition was obtained in the same manner as in Example 2, except that 2 g of 2-ethyl-4-methylimidazole was used instead of hishicolin PX-4ET.
ヒシコーリンＰＸ－４ＥＴに変えて２－エチル－４－メチルイミダゾールを２ｇ用いた以外は実施例２と同様にして樹脂組成物を得た。 [Comparative Example 1]
A resin composition was obtained in the same manner as in Example 2, except that 2 g of 2-ethyl-4-methylimidazole was used instead of hishicolin PX-4ET.
［比較例２］
ヒシコーリンＰＸ－４ＥＴを使用しないこと以外は実施例２と同様にして樹脂組成物を得た。 [Comparative Example 2]
A resin composition was obtained in the same manner as in Example 2 except that Hishicolin PX-4ET was not used.
ヒシコーリンＰＸ－４ＥＴを使用しないこと以外は実施例２と同様にして樹脂組成物を得た。 [Comparative Example 2]
A resin composition was obtained in the same manner as in Example 2 except that Hishicolin PX-4ET was not used.
［評価結果］
実施例及び比較例で得られた樹脂組成物を用いて以下の評価を行った。その結果を表１に示す。 [Evaluation results]
The following evaluations were performed using the resin compositions obtained in Examples and Comparative Examples. Table 1 shows the results.
実施例及び比較例で得られた樹脂組成物を用いて以下の評価を行った。その結果を表１に示す。 [Evaluation results]
The following evaluations were performed using the resin compositions obtained in Examples and Comparative Examples. Table 1 shows the results.
＜硬化性＞
前記実施例及び比較例で得られた樹脂組成物をアルミカップの中に２０ｇ秤量した後、８０℃で８０分加熱硬化させた。得られたサンプルの硬化度をＪＩＳ Ｋ ７１４８－１に準拠した方法に従って測定した。この時。硬化度が９０％以上の場合を＋、９０％未満の場合を－とした。 <Curability>
After weighing 20 g of the resin compositions obtained in the above Examples and Comparative Examples into an aluminum cup, the resin composition was cured by heating at 80° C. for 80 minutes. The degree of cure of the obtained sample was measured according to the method according to JIS K 7148-1. At this time. When the degree of curing was 90% or more, it was rated as +, and when it was less than 90%, it was rated -.
前記実施例及び比較例で得られた樹脂組成物をアルミカップの中に２０ｇ秤量した後、８０℃で８０分加熱硬化させた。得られたサンプルの硬化度をＪＩＳ Ｋ ７１４８－１に準拠した方法に従って測定した。この時。硬化度が９０％以上の場合を＋、９０％未満の場合を－とした。 <Curability>
After weighing 20 g of the resin compositions obtained in the above Examples and Comparative Examples into an aluminum cup, the resin composition was cured by heating at 80° C. for 80 minutes. The degree of cure of the obtained sample was measured according to the method according to JIS K 7148-1. At this time. When the degree of curing was 90% or more, it was rated as +, and when it was less than 90%, it was rated -.
＜非着色性＞
前記実施例及び比較例より得られた樹脂組成物３３ｇを、ローラーを用いてガラス繊維（Ｕ－Ｅ－１２００ｇ／ｍ２－１３００ｍｍ， Ｓａｅｒｔｅｘ製）１００ｇに対して含浸させた。その後、樹脂を含浸させたガラス繊維を８０℃の恒温槽に入れて８０分加熱硬化させた。得られた繊維強化プラスチックの着色の有無を目視により確認した。硬化前の色目から変化無いと判断されたものを＋、硬化前の色目から変化が確認されたものを－とした。 <Non-coloring>
100 g of glass fiber (UE-1200 g/m 2 -1300 mm, manufactured by Saertex) was impregnated with 33 g of the resin composition obtained in the above examples and comparative examples using a roller. After that, the resin-impregnated glass fiber was placed in a constant temperature bath at 80° C. and cured by heating for 80 minutes. The presence or absence of coloring of the obtained fiber-reinforced plastic was visually confirmed. When it was determined that there was no change from the color before curing, it was rated as +, and when it was confirmed that there was a change from the color before curing, it was rated as -.
前記実施例及び比較例より得られた樹脂組成物３３ｇを、ローラーを用いてガラス繊維（Ｕ－Ｅ－１２００ｇ／ｍ２－１３００ｍｍ， Ｓａｅｒｔｅｘ製）１００ｇに対して含浸させた。その後、樹脂を含浸させたガラス繊維を８０℃の恒温槽に入れて８０分加熱硬化させた。得られた繊維強化プラスチックの着色の有無を目視により確認した。硬化前の色目から変化無いと判断されたものを＋、硬化前の色目から変化が確認されたものを－とした。 <Non-coloring>
100 g of glass fiber (UE-1200 g/m 2 -1300 mm, manufactured by Saertex) was impregnated with 33 g of the resin composition obtained in the above examples and comparative examples using a roller. After that, the resin-impregnated glass fiber was placed in a constant temperature bath at 80° C. and cured by heating for 80 minutes. The presence or absence of coloring of the obtained fiber-reinforced plastic was visually confirmed. When it was determined that there was no change from the color before curing, it was rated as +, and when it was confirmed that there was a change from the color before curing, it was rated as -.
なお、表１において、＊１～＊７は以下のとおりである。
＊１：株式会社ＡＤＥＫＡ製 アデカレジン；ビスフェノール型エポキシ樹脂、エポキシ当量１９０ｇ／ｅｑ．
＊２：株式会社ＡＤＥＫＡ製 アデカグリシロール；ネオペンチルグリコール型エポキシ樹脂、エポキシ当量１４０ｇ／ｅｑ．
＊３：ハンツマン社製 ジェファーミン；ポリオキシプロピレンジアミン
＊４：日本化学工業株式会社製 ヒシコーリン；テトラブチルホスホニウム Ｏ，Ｏ－ジエチルホスホロジチオエート
＊５：信越シリコーン株式会社製；γ－グリシドキシプロピルトリメトキシシラン
＊６：株式会社ＡＤＥＫＡ製 アデカグリシロール；ｐ－ｔｅｒｔブチルフェニルグリシジルエーテル
＊７：２－エチル－４－メチルイミダゾール In Table 1, *1 to *7 are as follows.
*1: Adeka resin manufactured by ADEKA Corporation; bisphenol type epoxy resin, epoxy equivalent of 190 g/eq.
*2: ADEKA CORPORATION ADEKA GLYCIROL; neopentyl glycol type epoxy resin, epoxy equivalent 140 g/eq.
*3: Jeffamine manufactured by Huntsman; Polyoxypropylenediamine *4: Hishicoline manufactured by Nippon Kagaku Kogyo Co., Ltd.; Propyltrimethoxysilane *6: ADEKA Co., Ltd. ADEKA GLYCIROL; p-tert butylphenyl glycidyl ether *7: 2-ethyl-4-methylimidazole
＊１：株式会社ＡＤＥＫＡ製 アデカレジン；ビスフェノール型エポキシ樹脂、エポキシ当量１９０ｇ／ｅｑ．
＊２：株式会社ＡＤＥＫＡ製 アデカグリシロール；ネオペンチルグリコール型エポキシ樹脂、エポキシ当量１４０ｇ／ｅｑ．
＊３：ハンツマン社製 ジェファーミン；ポリオキシプロピレンジアミン
＊４：日本化学工業株式会社製 ヒシコーリン；テトラブチルホスホニウム Ｏ，Ｏ－ジエチルホスホロジチオエート
＊５：信越シリコーン株式会社製；γ－グリシドキシプロピルトリメトキシシラン
＊６：株式会社ＡＤＥＫＡ製 アデカグリシロール；ｐ－ｔｅｒｔブチルフェニルグリシジルエーテル
＊７：２－エチル－４－メチルイミダゾール In Table 1, *1 to *7 are as follows.
*1: Adeka resin manufactured by ADEKA Corporation; bisphenol type epoxy resin, epoxy equivalent of 190 g/eq.
*2: ADEKA CORPORATION ADEKA GLYCIROL; neopentyl glycol type epoxy resin, epoxy equivalent 140 g/eq.
*3: Jeffamine manufactured by Huntsman; Polyoxypropylenediamine *4: Hishicoline manufactured by Nippon Kagaku Kogyo Co., Ltd.; Propyltrimethoxysilane *6: ADEKA Co., Ltd. ADEKA GLYCIROL; p-tert butylphenyl glycidyl ether *7: 2-ethyl-4-methylimidazole
表１からわかるように、本発明の繊維強化プラスチック用樹脂組成物は硬化性に優れ、これを用いて得られる繊維強化プラスチックは、非着色性に優れている。
As can be seen from Table 1, the resin composition for fiber-reinforced plastics of the present invention has excellent curability, and the fiber-reinforced plastic obtained using it has excellent non-coloring properties.
本発明の繊維強化プラスチック用樹脂組成物は、硬化性に優れ、且つ非着色性に優れた繊維強化プラスチックを提供することができることから、美観に優れた成形体を提供することが可能である。
Since the resin composition for fiber-reinforced plastics of the present invention can provide fiber-reinforced plastics with excellent curability and excellent non-coloring properties, it is possible to provide molded articles with excellent appearance.
Claims (7)
- （Ａ）成分：エポキシ樹脂、（Ｂ）成分：ポリオキシアルキレンポリアミン及び（Ｃ）成分：下記式（１）で表される化合物の中から選ばれる少なくとも一種を含有する繊維強化プラスチック用樹脂組成物。
（式中、Ｒ１～Ｒ６は、それぞれ独立して、炭素数１～１０の炭化水素基を表し、Ｘ１～Ｘ４は、それぞれ独立して、酸素原子又は硫黄原子を表す。） (A) component: epoxy resin, (B) component: polyoxyalkylene polyamine, and (C) component: a resin composition for fiber-reinforced plastics containing at least one selected from compounds represented by the following formula (1) .
(In the formula, R 1 to R 6 each independently represent a hydrocarbon group having 1 to 10 carbon atoms, and X 1 to X 4 each independently represent an oxygen atom or a sulfur atom.) - （Ｂ）成分であるポリオキシアルキレンポリアミンが、重量平均分子量２００～５０００のポリオキシプロピレンポリアミンである、請求項１に記載の繊維強化プラスチック用樹脂組成物。 The resin composition for fiber-reinforced plastics according to claim 1, wherein the polyoxyalkylene polyamine as component (B) is a polyoxypropylene polyamine having a weight average molecular weight of 200 to 5,000.
- （Ｃ）成分の含有量が、（Ｂ）成分１００質量部に対して０．０１～２０質量部である、請求項１又は２に記載の繊維強化プラスチック用樹脂組成物。 The resin composition for fiber-reinforced plastics according to claim 1 or 2, wherein the content of component (C) is 0.01 to 20 parts by mass per 100 parts by mass of component (B).
- さらに、（Ｄ）成分：シランカップリング剤を含有する、請求項１～３の何れか一項に記載の繊維強化プラスチック用樹脂組成物。 The resin composition for fiber-reinforced plastics according to any one of claims 1 to 3, further comprising (D) component: a silane coupling agent.
- さらに、（Ｅ）成分：反応性希釈剤を含有する、請求項１～４の何れか一項に記載の繊維強化プラスチック用樹脂組成物。 The resin composition for fiber-reinforced plastics according to any one of claims 1 to 4, further comprising (E) component: a reactive diluent.
- 請求項１～５の何れか一項に記載の繊維強化プラスチック用樹脂組成物の硬化物を含有してなる、繊維強化プラスチック。 A fiber-reinforced plastic containing a cured product of the resin composition for fiber-reinforced plastic according to any one of claims 1 to 5.
- 請求項１～５の何れか一項に記載の繊維強化プラスチック用樹脂組成物及び強化繊維を含有する組成物を硬化させてなる、繊維強化プラスチック。
A fiber-reinforced plastic obtained by curing a composition containing the resin composition for fiber-reinforced plastic according to any one of claims 1 to 5 and a reinforcing fiber.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2022022447 | 2022-02-16 | ||
| JP2022-022447 | 2022-02-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2023157750A1 true WO2023157750A1 (en) | 2023-08-24 |
Family
ID=87578119
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/JP2023/004329 WO2023157750A1 (en) | 2022-02-16 | 2023-02-09 | Resin composition for fiber-reinforced plastic, and fiber-reinforced plastic |
Country Status (2)
| Country | Link |
|---|---|
| TW (1) | TW202344548A (en) |
| WO (1) | WO2023157750A1 (en) |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5847015A (en) * | 1981-09-14 | 1983-03-18 | Mitsui Tekisako Chem Kk | Curing agent for epoxy resin |
| JP2001151862A (en) * | 1999-11-22 | 2001-06-05 | Tosoh Corp | Epoxy resin composition |
| JP2008266541A (en) * | 2007-04-25 | 2008-11-06 | Sanyo Chem Ind Ltd | Epoxy resin hardener |
| WO2019013025A1 (en) * | 2017-07-13 | 2019-01-17 | 東レ株式会社 | Molded article and production method therefor |
| JP2021088639A (en) * | 2019-12-03 | 2021-06-10 | 株式会社Adeka | Resin composition, and cured product thereof, fiber-reinforced plastic, and method for making fiber-reinforced plastic flame-resistant |
-
2023
- 2023-02-09 WO PCT/JP2023/004329 patent/WO2023157750A1/en unknown
- 2023-02-13 TW TW112104929A patent/TW202344548A/en unknown
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5847015A (en) * | 1981-09-14 | 1983-03-18 | Mitsui Tekisako Chem Kk | Curing agent for epoxy resin |
| JP2001151862A (en) * | 1999-11-22 | 2001-06-05 | Tosoh Corp | Epoxy resin composition |
| JP2008266541A (en) * | 2007-04-25 | 2008-11-06 | Sanyo Chem Ind Ltd | Epoxy resin hardener |
| WO2019013025A1 (en) * | 2017-07-13 | 2019-01-17 | 東レ株式会社 | Molded article and production method therefor |
| JP2021088639A (en) * | 2019-12-03 | 2021-06-10 | 株式会社Adeka | Resin composition, and cured product thereof, fiber-reinforced plastic, and method for making fiber-reinforced plastic flame-resistant |
Also Published As
| Publication number | Publication date |
|---|---|
| TW202344548A (en) | 2023-11-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US11186692B2 (en) | Epoxy resin composition, fiber reinforced composite material, molded article and pressure vessel | |
| US10815373B2 (en) | Thermoset resin composite materials comprising inter-laminar toughening particles | |
| JP5715055B2 (en) | Structural composites with improved toughness | |
| JP2015180753A (en) | Curable epoxy resin compositions and composites made thereof | |
| US9574081B2 (en) | Epoxy-resin composition, and film, prepreg and fiber-reinforced plastic using the same | |
| AU2015362688B2 (en) | Modified resin systems suitable for liquid resin infusion | |
| CN110577723A (en) | Epoxy resin composition, and film, prepreg and fiber-reinforced plastic using same | |
| US10344132B2 (en) | Epoxy resin composition, prepreg and fiber reinforced composite material | |
| KR101805677B1 (en) | Epoxy resin composition for aramid-fiber-reinforced composite material, prepreg, and fiber-reinforced composite material | |
| US20150284562A1 (en) | Curable epoxy composition and a composite made therefrom | |
| US20230279219A1 (en) | Epoxy resin composition, prepreg, and fiber-reinforced composite material | |
| WO2023157750A1 (en) | Resin composition for fiber-reinforced plastic, and fiber-reinforced plastic | |
| CN114729105A (en) | Matrix resins with high transparency, low yellowing and high glass transition temperature for laminates | |
| CN114728488A (en) | PEO-PPO-PEO triblock copolymers as additives for epoxide-anhydride systems | |
| JP2017008317A (en) | Epoxy resin composition, fiber reinforced composite material, molded article and pressure container | |
| WO2020184324A1 (en) | Resin composition for fiber-reinforced plastic, and fiber-reinforced plastic containing said composition | |
| CN114651025B (en) | Curable composition, cured product, fiber-reinforced composite material, molded article, and method for producing same | |
| JP2011001442A (en) | Epoxy resin composition, fiber-reinforced composite material, and manufacturing method for fiber-reinforced composite material | |
| US11725103B2 (en) | Curable resin composition and fiber reinforced resin matrix composite material | |
| WO2023089997A1 (en) | Curable composition, cured product, fiber reinforced composite material, and fiber reinforced resin molded article | |
| JP2023131746A (en) | Matrix resin composition, prepreg, and carbon fiber composite material | |
| JPWO2018131580A1 (en) | Epoxy resin composition, cured epoxy resin, prepreg, fiber reinforced composite material, block copolymer and method for producing the same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 23756276 Country of ref document: EP Kind code of ref document: A1 |
|
| ENP | Entry into the national phase |
Ref document number: 2024501334 Country of ref document: JP Kind code of ref document: A |