JP7335891B2 - 不飽和ポリエステル樹脂組成物、成形材料、成形品、および、電動車両のバッテリーパック筐体 - Google Patents
不飽和ポリエステル樹脂組成物、成形材料、成形品、および、電動車両のバッテリーパック筐体 Download PDFInfo
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- JP7335891B2 JP7335891B2 JP2020553237A JP2020553237A JP7335891B2 JP 7335891 B2 JP7335891 B2 JP 7335891B2 JP 2020553237 A JP2020553237 A JP 2020553237A JP 2020553237 A JP2020553237 A JP 2020553237A JP 7335891 B2 JP7335891 B2 JP 7335891B2
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- unsaturated polyester
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- polyester resin
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- 229920006337 unsaturated polyester resin Polymers 0.000 title claims description 84
- 239000000203 mixture Substances 0.000 title claims description 82
- 239000012778 molding material Substances 0.000 title claims description 47
- 238000002156 mixing Methods 0.000 claims description 58
- 150000007519 polyprotic acids Polymers 0.000 claims description 57
- 239000003063 flame retardant Substances 0.000 claims description 49
- 229920005989 resin Polymers 0.000 claims description 49
- 239000011347 resin Substances 0.000 claims description 49
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 claims description 43
- 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 claims description 36
- 239000003795 chemical substances by application Substances 0.000 claims description 34
- 229920006305 unsaturated polyester Polymers 0.000 claims description 31
- 239000000178 monomer Substances 0.000 claims description 26
- 229910052782 aluminium Inorganic materials 0.000 claims description 23
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 23
- 238000006116 polymerization reaction Methods 0.000 claims description 22
- 239000012783 reinforcing fiber Substances 0.000 claims description 19
- 229920002689 polyvinyl acetate Polymers 0.000 claims description 17
- 239000011118 polyvinyl acetate Substances 0.000 claims description 17
- 150000005846 sugar alcohols Polymers 0.000 claims description 16
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 11
- 239000000945 filler Substances 0.000 claims description 11
- 229920001225 polyester resin Polymers 0.000 claims description 11
- 239000004645 polyester resin Substances 0.000 claims description 11
- 229910052698 phosphorus Inorganic materials 0.000 claims description 10
- 239000011574 phosphorus Substances 0.000 claims description 10
- -1 ether diol Chemical class 0.000 description 46
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 42
- 239000002253 acid Substances 0.000 description 40
- 239000000047 product Substances 0.000 description 39
- 239000004593 Epoxy Substances 0.000 description 37
- 238000006243 chemical reaction Methods 0.000 description 33
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 32
- 229910052751 metal Inorganic materials 0.000 description 30
- 239000002184 metal Substances 0.000 description 30
- 229920001567 vinyl ester resin Polymers 0.000 description 30
- 239000003822 epoxy resin Substances 0.000 description 27
- 229920000647 polyepoxide Polymers 0.000 description 27
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 21
- 229920006395 saturated elastomer Polymers 0.000 description 21
- 150000001875 compounds Chemical class 0.000 description 19
- 229920000728 polyester Polymers 0.000 description 19
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 18
- 239000003112 inhibitor Substances 0.000 description 18
- 150000007513 acids Chemical class 0.000 description 17
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 17
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 14
- 239000003054 catalyst Substances 0.000 description 12
- 239000003677 Sheet moulding compound Substances 0.000 description 11
- 239000003365 glass fiber Substances 0.000 description 11
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical group CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 10
- 125000001931 aliphatic group Chemical group 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 10
- 238000000465 moulding Methods 0.000 description 10
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- 238000003786 synthesis reaction Methods 0.000 description 10
- 239000000654 additive Substances 0.000 description 9
- 150000001298 alcohols Chemical class 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 9
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- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- 229910052736 halogen Inorganic materials 0.000 description 8
- 150000002367 halogens Chemical class 0.000 description 8
- 229920001276 ammonium polyphosphate Polymers 0.000 description 7
- 239000007795 chemical reaction product Substances 0.000 description 7
- 238000000034 method Methods 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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- 239000003086 colorant Substances 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
- 150000002739 metals Chemical class 0.000 description 6
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 6
- 230000035484 reaction time Effects 0.000 description 6
- 229920001187 thermosetting polymer Polymers 0.000 description 6
- 238000009736 wetting Methods 0.000 description 6
- 239000000080 wetting agent Substances 0.000 description 6
- 239000004114 Ammonium polyphosphate Substances 0.000 description 5
- 239000004793 Polystyrene Substances 0.000 description 5
- 150000008065 acid anhydrides Chemical class 0.000 description 5
- 235000019826 ammonium polyphosphate Nutrition 0.000 description 5
- 238000000748 compression moulding Methods 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical class C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 5
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 5
- 238000004519 manufacturing process Methods 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
- 238000006068 polycondensation reaction Methods 0.000 description 5
- 229920002223 polystyrene Polymers 0.000 description 5
- 238000007573 shrinkage measurement Methods 0.000 description 5
- 239000000779 smoke Substances 0.000 description 5
- 239000002562 thickening agent Substances 0.000 description 5
- 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 4
- 229920000049 Carbon (fiber) Polymers 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
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- 229910000019 calcium carbonate Inorganic materials 0.000 description 4
- 239000004917 carbon fiber Substances 0.000 description 4
- 229910001873 dinitrogen Inorganic materials 0.000 description 4
- 125000003700 epoxy group Chemical group 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000000691 measurement method Methods 0.000 description 4
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 4
- 235000021317 phosphate Nutrition 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000001361 adipic acid Substances 0.000 description 3
- 235000011037 adipic acid Nutrition 0.000 description 3
- 125000002723 alicyclic group Chemical group 0.000 description 3
- 238000007664 blowing Methods 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 238000002485 combustion reaction Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 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
- 239000000395 magnesium oxide Substances 0.000 description 3
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 3
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 3
- 239000010452 phosphate Substances 0.000 description 3
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 description 3
- 238000012643 polycondensation polymerization Methods 0.000 description 3
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- 239000000843 powder Substances 0.000 description 3
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000010959 steel 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
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 3
- 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 2
- GOHPTLYPQCTZSE-UHFFFAOYSA-N 2,2-dimethylsuccinic acid Chemical compound OC(=O)C(C)(C)CC(O)=O GOHPTLYPQCTZSE-UHFFFAOYSA-N 0.000 description 2
- JHJUYGMZIWDHMO-UHFFFAOYSA-N 2,6-dibromo-4-(3,5-dibromo-4-hydroxyphenyl)sulfonylphenol Chemical compound C1=C(Br)C(O)=C(Br)C=C1S(=O)(=O)C1=CC(Br)=C(O)C(Br)=C1 JHJUYGMZIWDHMO-UHFFFAOYSA-N 0.000 description 2
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-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
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- CKNCVRMXCLUOJI-UHFFFAOYSA-N 3,3'-dibromobisphenol A Chemical compound C=1C=C(O)C(Br)=CC=1C(C)(C)C1=CC=C(O)C(Br)=C1 CKNCVRMXCLUOJI-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
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 2
- 239000004412 Bulk moulding compound Substances 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-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
- 238000007259 addition reaction Methods 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 229910000287 alkaline earth metal oxide Inorganic materials 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
- 238000005452 bending Methods 0.000 description 2
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- WUOBERCRSABHOT-UHFFFAOYSA-N diantimony Chemical compound [Sb]#[Sb] WUOBERCRSABHOT-UHFFFAOYSA-N 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000012784 inorganic fiber Substances 0.000 description 2
- 239000012796 inorganic flame retardant Substances 0.000 description 2
- 238000004255 ion exchange chromatography Methods 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 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
- 238000005259 measurement Methods 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 229910017464 nitrogen compound Inorganic materials 0.000 description 2
- 150000002830 nitrogen compounds Chemical class 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- GUSFEBGYPWJUSS-UHFFFAOYSA-N pentaazanium;[oxido(phosphonatooxy)phosphoryl] phosphate Chemical compound [NH4+].[NH4+].[NH4+].[NH4+].[NH4+].[O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O GUSFEBGYPWJUSS-UHFFFAOYSA-N 0.000 description 2
- 230000002093 peripheral effect Effects 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-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
- 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
- 239000000126 substance Substances 0.000 description 2
- 229940014800 succinic anhydride Drugs 0.000 description 2
- WPZJSWWEEJJSIZ-UHFFFAOYSA-N tetrabromobisphenol-F Natural products C1=C(Br)C(O)=C(Br)C=C1CC1=CC(Br)=C(O)C(Br)=C1 WPZJSWWEEJJSIZ-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
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- 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
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Description
非臭素化ビスフェノール化合物として、例えば、ビスフェノールA、ビスフェノールF、ビスフェノールSなどが挙げられ、好ましくは、ビスフェノールAが挙げられる。
このような非臭素化エポキシ化合物として、例えば、ビスフェノールA型エポキシ樹脂、ビスフェノールF型エポキシ樹脂、ビスフェノールS型エポキシ樹脂などが挙げられる。
このような臭素化ビスフェノール化合物として、例えば、テトラブロモビスフェノールA([2,2-ビス(3,5-ジブロモ-4-ヒドロキシフェニル)プロパン)、ジブロモビスフェノールA、テトラブロモビスフェノールF、テトラブロモビスフェノールSなどが挙げられる。
このような臭素化エポキシ化合物として、例えば、テトラブロモビスフェノールA型エポキシ樹脂、ジブロモビスフェノールA型エポキシ樹脂、テトラブロモビスフェノールF型エポキシ樹脂、テトラブロモビスフェノールS型エポキシ樹脂などが挙げられる。
1.不飽和ポリエステル樹脂の調製
合成例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、無水マレイン酸10.0モル、プロピレングリコール6.5モル、ネオペンチルグリコール4.0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、酸価が26.5mgKOH/gの不飽和ポリエステルを得た。なお、酸価の測定方法は、JIS K6901(2008年)に準拠した。得られた不飽和ポリエステル100質量部に対し、重合禁止剤としてハイドロキノンを0.01質量部、スチレンを66.7質量部添加し、これらを均一に混合して、不飽和ポリエステル樹脂(スチレン含有量40%)を得た。
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3.3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20mgKOH/gになった時点で150℃まで冷却し、無水マレイン酸6.7モルを仕込み、再び210℃~220℃で反応させ、酸価27.5mgKOH/gの不飽和ポリエステルを得た。得られた不飽和ポリエステル100質量部に対し、重合禁止剤としてハイドロキノンを0.01質量部、スチレンを66.7質量部添加し、これらを均一に混合して、不飽和ポリエステル樹脂(スチレン含有率40%)を得た。
2.飽和ポリエステル樹脂の調製
合成例3
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4.0モル、ネオペンチルグリコール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、アジピン酸6.0モルを仕込み、再び210℃~220℃で反応させ、酸価9.5mgKOH/gの飽和ポリエステルを得た。得られた飽和ポリエステル100質量部に対し、重合禁止剤としてハイドロキノンを0.01質量部、スチレンを66.7質量部添加し、これらを均一に混合して、飽和ポリエステル樹脂(スチレン含有率40%)を得た。
3.ビニルエステル樹脂の調製
合成例4
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 114質量部(1.0当量)、ビスフェノールA型エポキシ樹脂(エポキシ当量185)555質量部(3.0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 0.15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335の非臭素化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 0.10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 1.50質量部、メタクリル酸 176質量部(2.05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8.5mgKOH/gのビニルエステルを得た。次いで、このビニルエステルにスチレン563質量部を加えることにより、スチレン40質量%含有のビニルエステル樹脂を得た。
4.臭素化ビニルエステル樹脂の調製
合成例5
合成例3と同様の反応容器に、臭素化エポキシ樹脂として、テトラブロモビスフェノールA型エポキシ樹脂(エポキシ当量400、臭素含有率48.0%)400質量部(1.0当量)、メタクリル酸 88.2質量部(1.025当量)、重合禁止剤としてハイドロキノン 0.05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 0.5質量部を添加し、空気を吹き込みながら110℃で8時間反応させ、酸価9.0mgKOH/gの臭素化ビニルエステルを得た。次いで、この臭素化ビニルエステルにスチレン325質量部を加えることにより、スチレン40質量%含有の臭素化ビニルエステル樹脂(臭素含有率23.6%)を得た。
5.不飽和ポリエステル樹脂組成物および成形材料の調製
実施例1
合成例1の不飽和ポリエステル樹脂60質量部(不飽和ポリエステル36質量部、スチレン24質量部)、低収縮化剤として、ポリ酢酸ビニル溶液(ポリ酢酸ビニルの40%スチレン溶液)15質量部(ポリ酢酸ビニル6質量部、スチレン9質量部)、および、合成例3の飽和ポリエステル樹脂20質量部(飽和ポリエステル12質量部、スチレン8質量部)、重合性単量体として、スチレン5質量部、難燃剤として、ホスフィン酸金属塩(OP1230(商品名、Exolit OP1230、クラリアントケミカルズ社製,リン含量23%)) 10質量部、重合禁止剤として、p-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、着色剤として、黒色ポリエステルトナー(カーボンブラックをポリエステル樹脂に分散させたもの)10質量部、水酸化アルミニウム(平均粒子径8μm)130質量部、湿潤分散剤として、リン酸ポリエステル 1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1および表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。
6.評価
(成形収縮率)
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。
評価基準:
◎:収縮率が、0以下であった。
○:収縮率が、0以上、0.10未満であった。
×:収縮率が、0.10以上であった。
成形収縮率測定平板作成と同様の手順で成形材料を成形し、厚み4mm、3mmおよび2.5mmの成形板を得た。成形板より試験片を切り出しUL規格(Underwriters Laboratories Inc.)のUL94規格(プラスチック材料燃焼性試験)に準拠して燃焼試験を実施した。厚さ4mm、厚さ3mm、厚さ2.5mmのそれぞれの試験片でV-0基準を満たすか評価した。その結果を表3および表4に示す。
評価基準:
◎:V-0基準(厚み2.5mm)に適合した。
○:V-0基準(厚み3mm)に適合した。
×:V-0基準(厚み4mm)に適合しなかった。
(線膨張係数)
成形収縮率測定で用いた平板状の成形品(厚み4mm)から、試験片(4mm×4mm×5mm)を切削加工し、熱機械分析装置(日立ハイテクサイエンス社製、EXSTAR TMA SS7100)で圧縮・膨張プローブを使用し、成形品の水平方向の線膨張係数を測定した。5℃/分の昇温速度で室温より100℃まで昇温し、50℃から80℃の範囲の線膨張係数を測定した。その結果を表3および表4に示す。
◎:アルミニウムの線膨張係数との差の絶対値が、0以上1.2未満
○:アルミニウムの線膨張係数との差の絶対値が、1.2以上2未満
△:アルミニウムの線膨張係数との差の絶対値が、2以上4未満
×:アルミニウムの線膨張係数との差の絶対値が、4以上
(発煙性)
上記難燃性試験で、厚み3mm試験片を使用した際のV-0判定試験において、燃焼時に黒煙が発生するか目視で観察した。
○:黒煙が発生しなかった。
×:黒煙が発生した。
<含浸状態の評価>
SMC製造直後にカッターナイフでキャリヤフィルムを剥ぎ取り、不飽和ポリエステル樹脂組成物とガラス繊維の含浸の程度を目視で評価した。
○:ガラス繊維が不飽和ポリエステル樹脂組成物で十分に濡らされ、不飽和ポリエステル樹脂組成物に含浸していないガラス繊維が観察されなかった。
×:部分的に、不飽和ポリエステル樹脂組成物に含浸していないガラス繊維が観察された。
熟成後の成形材料(SMC)のキャリヤフィルムをカッターナイフで剥がし、フィルム剥離性を評価した。
○:SMCにタックが少なくスムーズにフィルムが剥がれた。
×:SMCに強いタックが観察された。または、フィルム剥離時に一部成分の分離が観察された。
成形収縮率測定で用いた平板状の成形品(厚み4mm)から、試験片を切り出し、JIS K6911(1995年)に準拠し、密度を測定した。その結果を表3および表4に示す。
成形収縮率測定で用いた平板状の成形品(厚み4mm)から、試験片(長さ80mm、幅10mm)を切り出し、JIS K7017(1999年)に準拠し、23℃および90℃において曲げ強さ、曲げ弾性率を測定した。その結果を表3および表4に示す。
(引張特性)
成形収縮率測定で用いた平板状の成形品(厚み4mm)から、試験片を切り出し、JIS K7164(2005年)に準拠し、23℃において引張強さ、引張弾性率を測定した。その結果を表3および表4に示す。
4 内側層
5 外側層
Claims (8)
- 不飽和ポリエステル、重合性単量体および低収縮化剤を含む樹脂成分と、水酸化アルミニウムと、難燃剤(水酸化アルミニウムを除く)とを含み、
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、80モル%以上であり、
前記不飽和ポリエステルの配合割合は、前記樹脂成分に対して、20質量%以上、60質量%以下であり、
前記低収縮化剤は、ポリ酢酸ビニルを含み、
ポリ酢酸ビニルの配合割合が、前記樹脂成分100質量部に対して、3質量部以上、10質量部以下であり、
前記水酸化アルミニウムの配合割合は、前記樹脂成分100質量部に対して、50質量部以上、130質量部以下であり、
前記難燃剤(水酸化アルミニウムを除く)の配合割合は、前記水酸化アルミニウム100質量部に対して、3質量部以上、80質量部以下であることを特徴とする、不飽和ポリエステル樹脂組成物。 - 前記難燃剤(水酸化アルミニウムを除く)の配合割合は、前記水酸化アルミニウム100質量部に対して、15質量部以上70質量部以下であることを特徴とする、請求項1に記載の不飽和ポリエステル樹脂組成物。
- 前記難燃剤(水酸化アルミニウムを除く)は、リン系難燃剤であることを特徴とする、請求項1に記載の不飽和ポリエステル樹脂組成物。
- 請求項1に記載の不飽和ポリエステル樹脂組成物と、強化繊維とを含み、
前記不飽和ポリエステル樹脂組成物のうち、前記水酸化アルミニウムおよび必要により配合される充填材を除いたフィラー除外成分の総量が、40体積%以上70体積%以下であることを特徴とする、成形材料。 - 請求項4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。
- 線膨張係数が、20ppm/℃以上、25ppm/℃以下であることを特徴とする、請求項5に記載の成形品。
- 電動車両のバッテリーパック筐体用であることを特徴とする、請求項5に記載の成形品。
- アルミニウム部材、および、請求項5に記載の成形品を一体的に備えることを特徴とする、電動車両のバッテリーパック筐体。
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