JP2021116330A - 成形材料および成形品 - Google Patents
成形材料および成形品 Download PDFInfo
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- JP2021116330A JP2021116330A JP2020009170A JP2020009170A JP2021116330A JP 2021116330 A JP2021116330 A JP 2021116330A JP 2020009170 A JP2020009170 A JP 2020009170A JP 2020009170 A JP2020009170 A JP 2020009170A JP 2021116330 A JP2021116330 A JP 2021116330A
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- Prior art keywords
- meth
- unsaturated polyester
- molding material
- mass
- acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 239000012778 molding material Substances 0.000 title claims abstract description 65
- 229920006305 unsaturated polyester Polymers 0.000 claims abstract description 68
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims abstract description 59
- 239000000203 mixture Substances 0.000 claims abstract description 40
- 239000000178 monomer Substances 0.000 claims abstract description 38
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 34
- 229920000049 Carbon (fiber) Polymers 0.000 claims abstract description 32
- 239000004917 carbon fiber Substances 0.000 claims abstract description 32
- 229920006337 unsaturated polyester resin Polymers 0.000 claims abstract description 29
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000000047 product Substances 0.000 claims description 54
- 150000007519 polyprotic acids Polymers 0.000 claims description 50
- 238000002156 mixing Methods 0.000 claims description 27
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 20
- 238000013329 compounding Methods 0.000 claims description 11
- 238000006116 polymerization reaction Methods 0.000 claims description 11
- 150000005846 sugar alcohols Polymers 0.000 claims description 10
- 239000007795 chemical reaction product Substances 0.000 claims description 8
- 239000000376 reactant Substances 0.000 abstract 1
- -1 unsaturated glycidyl compound Chemical class 0.000 description 46
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical group C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 33
- 239000002253 acid Substances 0.000 description 24
- 230000000052 comparative effect Effects 0.000 description 19
- 239000003795 chemical substances by application Substances 0.000 description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- IISBACLAFKSPIT-UHFFFAOYSA-N Bisphenol A Natural products C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 10
- 239000012783 reinforcing fiber Substances 0.000 description 10
- 239000003063 flame retardant Substances 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 239000003677 Sheet moulding compound Substances 0.000 description 8
- 125000001931 aliphatic group Chemical group 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 229920001971 elastomer Polymers 0.000 description 8
- 239000000806 elastomer Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 7
- 150000007513 acids Chemical class 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- 239000002562 thickening agent Substances 0.000 description 7
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 239000002270 dispersing agent Substances 0.000 description 6
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical group CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 6
- 239000003112 inhibitor Substances 0.000 description 6
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 6
- 238000000465 moulding Methods 0.000 description 6
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N 1,4-Benzenediol Natural products OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 5
- 125000002723 alicyclic group Chemical group 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 239000003086 colorant Substances 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 239000000945 filler Substances 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 239000003365 glass fiber Substances 0.000 description 5
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 150000008065 acid anhydrides Chemical class 0.000 description 4
- 229920001228 polyisocyanate Polymers 0.000 description 4
- 239000005056 polyisocyanate Substances 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- 229920002725 thermoplastic elastomer Polymers 0.000 description 4
- QEQBMZQFDDDTPN-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy benzenecarboperoxoate Chemical compound CC(C)(C)OOOC(=O)C1=CC=CC=C1 QEQBMZQFDDDTPN-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 3
- 238000005452 bending Methods 0.000 description 3
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 3
- 229920001400 block copolymer Polymers 0.000 description 3
- 238000000748 compression moulding Methods 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- BXOUVIIITJXIKB-UHFFFAOYSA-N ethene;styrene Chemical group C=C.C=CC1=CC=CC=C1 BXOUVIIITJXIKB-UHFFFAOYSA-N 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- NWVVVBRKAWDGAB-UHFFFAOYSA-N hydroquinone methyl ether Natural products COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 3
- 238000005470 impregnation Methods 0.000 description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229940059574 pentaerithrityl Drugs 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 235000013772 propylene glycol Nutrition 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- 229920001567 vinyl ester resin Polymers 0.000 description 3
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 3
- GOHPTLYPQCTZSE-UHFFFAOYSA-N 2,2-dimethylsuccinic acid Chemical compound OC(=O)C(C)(C)CC(O)=O GOHPTLYPQCTZSE-UHFFFAOYSA-N 0.000 description 2
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 2
- DSKYSDCYIODJPC-UHFFFAOYSA-N 2-butyl-2-ethylpropane-1,3-diol Chemical compound CCCCC(CC)(CO)CO DSKYSDCYIODJPC-UHFFFAOYSA-N 0.000 description 2
- WXUAQHNMJWJLTG-UHFFFAOYSA-N 2-methylbutanedioic acid Chemical compound OC(=O)C(C)CC(O)=O WXUAQHNMJWJLTG-UHFFFAOYSA-N 0.000 description 2
- VTWDKFNVVLAELH-UHFFFAOYSA-N 2-methylcyclohexa-2,5-diene-1,4-dione Chemical compound CC1=CC(=O)C=CC1=O VTWDKFNVVLAELH-UHFFFAOYSA-N 0.000 description 2
- XJMMNTGIMDZPMU-UHFFFAOYSA-N 3-methylglutaric acid Chemical compound OC(=O)CC(C)CC(O)=O XJMMNTGIMDZPMU-UHFFFAOYSA-N 0.000 description 2
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 2
- 239000004412 Bulk moulding compound Substances 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 241000209094 Oryza Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- 229910019142 PO4 Inorganic materials 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
- 125000005396 acrylic acid ester group Chemical group 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- HIFVAOIJYDXIJG-UHFFFAOYSA-N benzylbenzene;isocyanic acid Chemical class N=C=O.N=C=O.C=1C=CC=CC=1CC1=CC=CC=C1 HIFVAOIJYDXIJG-UHFFFAOYSA-N 0.000 description 2
- 238000007664 blowing Methods 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 2
- 239000000347 magnesium hydroxide Substances 0.000 description 2
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000000691 measurement method Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-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
- 230000035484 reaction time Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 150000003839 salts Chemical class 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
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 2
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 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
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- FVQMJJQUGGVLEP-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOOC(C)(C)C FVQMJJQUGGVLEP-UHFFFAOYSA-N 0.000 description 1
- HSLFISVKRDQEBY-UHFFFAOYSA-N 1,1-bis(tert-butylperoxy)cyclohexane Chemical compound CC(C)(C)OOC1(OOC(C)(C)C)CCCCC1 HSLFISVKRDQEBY-UHFFFAOYSA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- 150000004057 1,4-benzoquinones Chemical class 0.000 description 1
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 1
- UNVGBIALRHLALK-UHFFFAOYSA-N 1,5-Hexanediol Chemical compound CC(O)CCCCO UNVGBIALRHLALK-UHFFFAOYSA-N 0.000 description 1
- WVUYYXUATWMVIT-UHFFFAOYSA-N 1-bromo-4-ethoxybenzene Chemical compound CCOC1=CC=C(Br)C=C1 WVUYYXUATWMVIT-UHFFFAOYSA-N 0.000 description 1
- CSGAUKGQUCHWDP-UHFFFAOYSA-N 1-hydroxy-2,2,6,6-tetramethylpiperidin-4-ol Chemical compound CC1(C)CC(O)CC(C)(C)N1O CSGAUKGQUCHWDP-UHFFFAOYSA-N 0.000 description 1
- KMEUSKGEUADGET-UHFFFAOYSA-N 1-hydroxy-2,2,6,6-tetramethylpiperidin-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)N1O KMEUSKGEUADGET-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
- BTUDGPVTCYNYLK-UHFFFAOYSA-N 2,2-dimethylglutaric acid Chemical compound OC(=O)C(C)(C)CCC(O)=O BTUDGPVTCYNYLK-UHFFFAOYSA-N 0.000 description 1
- KLZYRCVPDWTZLH-UHFFFAOYSA-N 2,3-dimethylsuccinic acid Chemical compound OC(=O)C(C)C(C)C(O)=O KLZYRCVPDWTZLH-UHFFFAOYSA-N 0.000 description 1
- UZWBDSQDACNUFX-UHFFFAOYSA-N 2-(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl)acetic acid Chemical compound CC1(C)CC(CC(O)=O)CC(C)(C)N1O UZWBDSQDACNUFX-UHFFFAOYSA-N 0.000 description 1
- UOQOHSUPANZDSJ-UHFFFAOYSA-N 2-(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl)octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCC(C(O)=O)C1CC(C)(C)N(O)C(C)(C)C1 UOQOHSUPANZDSJ-UHFFFAOYSA-N 0.000 description 1
- WAVTZYKJTMZICQ-UHFFFAOYSA-N 2-(2-methylbutan-2-ylperoxy)propan-2-yl hydrogen carbonate Chemical compound CCC(C)(C)OOC(C)(C)OC(O)=O WAVTZYKJTMZICQ-UHFFFAOYSA-N 0.000 description 1
- IEMBFTKNPXENSE-UHFFFAOYSA-N 2-(2-methylpentan-2-ylperoxy)propan-2-yl hydrogen carbonate Chemical compound CCCC(C)(C)OOC(C)(C)OC(O)=O IEMBFTKNPXENSE-UHFFFAOYSA-N 0.000 description 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
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- WFUUAJVRMXKBBI-UHFFFAOYSA-N 2-[1-(2-hydroxyethyl)cyclohexyl]ethanol Chemical compound OCCC1(CCO)CCCCC1 WFUUAJVRMXKBBI-UHFFFAOYSA-N 0.000 description 1
- JVGDVPVEKJSWIO-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)cyclohexyl]ethanol Chemical compound OCCC1CCC(CCO)CC1 JVGDVPVEKJSWIO-UHFFFAOYSA-N 0.000 description 1
- SBYMUDUGTIKLCR-UHFFFAOYSA-N 2-chloroethenylbenzene Chemical compound ClC=CC1=CC=CC=C1 SBYMUDUGTIKLCR-UHFFFAOYSA-N 0.000 description 1
- OZNSZTOTRJIEFL-UHFFFAOYSA-N 2-ethyl-2-(2-ethylhexylperoxy)hexanoic acid Chemical compound CCCCC(CC)COOC(CC)(C(O)=O)CCCC OZNSZTOTRJIEFL-UHFFFAOYSA-N 0.000 description 1
- PDZYPKCJRWNIAU-UHFFFAOYSA-N 2-ethyl-2-pentylperoxyhexanoic acid Chemical compound CCCCCOOC(CC)(C(O)=O)CCCC PDZYPKCJRWNIAU-UHFFFAOYSA-N 0.000 description 1
- ZJVMHPVIAUKERS-UHFFFAOYSA-N 2-hexylbutanedioic acid Chemical compound CCCCCCC(C(O)=O)CC(O)=O ZJVMHPVIAUKERS-UHFFFAOYSA-N 0.000 description 1
- WXDJDZIIPSOZAH-UHFFFAOYSA-N 2-methylpentan-2-yl benzenecarboperoxoate Chemical compound CCCC(C)(C)OOC(=O)C1=CC=CC=C1 WXDJDZIIPSOZAH-UHFFFAOYSA-N 0.000 description 1
- NKHJXJWYBPKMEI-UHFFFAOYSA-N 2-methylpentan-2-yl ethaneperoxoate Chemical compound CCCC(C)(C)OOC(C)=O NKHJXJWYBPKMEI-UHFFFAOYSA-N 0.000 description 1
- QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical compound OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 description 1
- BQARUDWASOOSRH-UHFFFAOYSA-N 2-tert-butylperoxypropan-2-yl hydrogen carbonate Chemical compound CC(C)(C)OOC(C)(C)OC(O)=O BQARUDWASOOSRH-UHFFFAOYSA-N 0.000 description 1
- DXIJHCSGLOHNES-UHFFFAOYSA-N 3,3-dimethylbut-1-enylbenzene Chemical compound CC(C)(C)C=CC1=CC=CC=C1 DXIJHCSGLOHNES-UHFFFAOYSA-N 0.000 description 1
- LFQTZIFRJDPZSE-UHFFFAOYSA-N 3-dodecyl-3-(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl)pyrrolidine-2,5-dione Chemical compound ON1C(CC(CC1(C)C)C1(C(=O)NC(C1)=O)CCCCCCCCCCCC)(C)C LFQTZIFRJDPZSE-UHFFFAOYSA-N 0.000 description 1
- JIGUICYYOYEXFS-UHFFFAOYSA-N 3-tert-butylbenzene-1,2-diol Chemical compound CC(C)(C)C1=CC=CC(O)=C1O JIGUICYYOYEXFS-UHFFFAOYSA-N 0.000 description 1
- SFXHWRCRQNGVLJ-UHFFFAOYSA-N 4-methoxy-TEMPO Chemical group COC1CC(C)(C)N([O])C(C)(C)C1 SFXHWRCRQNGVLJ-UHFFFAOYSA-N 0.000 description 1
- GVNWZKBFMFUVNX-UHFFFAOYSA-N Adipamide Chemical compound NC(=O)CCCCC(N)=O GVNWZKBFMFUVNX-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
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Landscapes
- Reinforced Plastic Materials (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Abstract
Description
1.グリシジルメタクリレート変性不飽和ポリエステルの調製
調製例1
温度計、窒素ガス導入管、還流冷却器および攪拌機を備えたフラスコに、イソフタル酸5.0モル、プロピレングリコール10.5モルを仕込み、窒素ガス雰囲気下で撹拌しながら200℃〜210℃で重縮合反応させた。その後、反応生成物の酸価が10mgKOH/gになった時点で150℃まで冷却し、無水マレイン酸5.0モルを仕込み、再び210℃〜220℃で酸価32.3mgKOH/gまで反応させた。反応生成物を150℃まで冷却し、空気を吹き込みながらグリシジルメタクリレート1.0モル、エステル化触媒としてトリエチルベンジルアンモニウムクロライドを、反応生成物100質量部に対して、0.15質量部添加して、酸価が3.1mgKOH/gになるまで反応させ、水酸基価51.9mgKOH/gのグリシジルメタクリレート変性不飽和ポリエステルを得た。なお、酸価及び水酸基価の測定方法は、JIS K6901(2008年)に準拠した。
配合処方を、表1の記載に従って変更した以外は、調製例1と同様に処理して、グリシジルメタクリレート変性不飽和ポリエステルを調製した。
配合処方を、表1の記載に従って変更した以外は、グリシジルメタクリレート未変性の不飽和ポリエステルを調製した。
2.ビニルエステルの調製
調製例10
攪拌機、還流冷却器、ガス導入管を備えたフラスコに、ビスフェノールA型エポキシ樹脂(エポキシ当量185)1850質量部(10.0当量)、ビスフェノールA 477質量部(4.18当量)、触媒としてトリエチルベンジルアンモニウムクロライド0.5質量部を仕込み、窒素を吹き込みながら、150℃で5時間反応させて、エポキシ当量が400のエポキシ樹脂を得た。120℃まで冷却後、重合禁止剤としてハイドロキノン2.0質量部、触媒としてトリエチルベンジルアンモニウムクロライド2.0質量部、メタクリル酸513質量部(5.97当量)を添加し、空気を吹き込みながら110℃で8時間反応させ、酸価8.0mgKOH/g、水酸基価208mgKOH/gのビニルエステルを得た。
3.成形材料の製造
実施例1
調製例1のグリシジルメタクリレート変性不飽和ポリエステル65質量部、スチレン35質量部、重合禁止剤として、パラベンゾキノン0.05質量部、硬化剤として、t−ブチルパーオキシベンゾエート1.0質量部、離型剤として、ステアリン酸亜鉛5質量部を混合して、不飽和ポリエステル樹脂組成物を得た。
配合処方を、表2の記載に従って変更した以外は、実施例1と同様に処理して、成形材料を得た。
4.評価
(含浸性)
各実施例、各比較例および各参考例について、成形時に、成形材料を幅方向にカットし、その断面を目視で観察した。含浸性を、以下の基準で評価した。その結果を表2に示す。
〇:成形材料の厚みの中央付近に樹脂成分の付着していない炭素繊維が確認されなかった。
△:成形材料の厚みの中央付近に樹脂成分の付着していない炭素繊維がわずかに確認された。
×:成形材料の厚みの中央付近に樹脂成分の付着していない炭素繊維が多数確認された。また、樹脂が付着されていない部分の面積も大きかった。
(曲げ強さおよび曲げ弾性率)
各実施例、各比較例および各参考例について、成形材料を、300mm×300mm平板金板を用いて、加熱圧縮成型して、厚み4mmの平板状の成形品を得た。
(密度)
各実施例、各比較例および各参考例について、上記曲げ強さ評価および曲げ弾性率評価で得られた成形品を用いて、25℃の水を用いてアルキメデス法により密度を求めた。その結果を表2に示す。
(比強度)
各実施例、各比較例および各参考例について、曲げ強度、密度の測定結果から、下記式(1)により比強度を算出した。その結果を表2に示す。
(比剛性)
各実施例、各比較例および各参考例について、曲げ弾性率、密度の測定結果から、下記式(2)により比剛性を算出した。その結果を表2に示す。
(強度(機械的物性))
各実施例、各比較例および各参考例について、強度(機械的物性)を、以下の基準で評価した。その結果を表2に示す。
〇:比強度が220MPa/(g/cm3)以上であり、かつ、比剛性が20(MPa)1/3/(g/cm3)以上であった。
△:以下の1)または2)のいずれかに該当した。
1)比強度が200MPa/(g/cm3)以上220MPa/(g/cm3)未満、かつ、比剛性が18(MPa)1/3/(g/cm3)以上であった。
2)比強度が、220MPa/(g/cm3)以上、かつ、比剛性が18(MPa)1/3/(g/cm3)以上20(MPa)1/3/(g/cm3)未満
×:比強度が200MPa/(g/cm3)未満、または、比剛性が18(MPa)1/3/(g/cm3)未満であった。
(耐候性)
各実施例、各比較例および各参考例について、上記曲げ強さ評価および曲げ弾性率評価で得られた成形品から、試験片(長さ150mm、幅70mm)を切り出した。
◎:チョーキングを確認できず、光沢の低下も確認できなかった。
〇:チョーキングを確認できなかったが、光沢の低下が確認できた。
△:僅かなチョーキングを確認でき、光沢の低下が確認できた。
×:顕著なチョーキングを確認でき、光沢の大幅な低下が確認できた。
5.考察
グリシジルメタクリレート変性不飽和ポリエステルと、強化繊維としての炭素繊維とを併用する実施例1〜実施例13は、不飽和ポリエステル(グリシジルメタクリレートよって変性されていない不飽和ポリエステル)と炭素繊維とを併用する比較例1に比べて、強度(比強度および比剛性)に優れる。
Claims (6)
- 不飽和ポリエステル樹脂組成物および炭素繊維を含み、
前記不飽和ポリエステル樹脂組成物は、不飽和ポリエステルおよびグリシジル(メタ)アクリレートの反応生成物と重合性単量体とを含むことを特徴とする、成形材料。 - 前記不飽和ポリエステルは、多塩基酸と、多価アルコールとの重合生成物であり、
前記多塩基酸は、エチレン性不飽和二重結合を有する多塩基酸を含み、
前記エチレン性不飽和二重結合を有する多塩基酸の配合割合は、前記多塩基酸100モル%に対して、35モル%以上55モル%以下であることを特徴とする、請求項1に記載の成形材料。 - 前記不飽和ポリエステルは、多塩基酸と、多価アルコールとの重合生成物であり、
前記グリシジル(メタ)アクリレートの配合割合が、前記多塩基酸100モル%に対して、3モル%以上15モル%以下であることを特徴とする、請求項1または2に記載の成形材料。 - 前記重合性単量体が、(メタ)アクリル酸エステルを含むことを特徴とする、請求項1〜3のいずれか一項に記載の成形材料。
- 前記不飽和ポリエステル樹脂組成物および前記炭素繊維の総量に対して、前記炭素繊維の配合割合が、40質量%以上60質量%以下であることを特徴とする、請求項1〜4のいずれか一項に記載の成形材料。
- 請求項1〜5のいずれか一項に記載の成形材料の硬化物を含むことを特徴とする、成形品。
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