JP2021147525A - 流動性向上剤、これを含む流動性向上剤組成物、これらを含む熱可塑性樹脂組成物、およびその成形体 - Google Patents
流動性向上剤、これを含む流動性向上剤組成物、これらを含む熱可塑性樹脂組成物、およびその成形体 Download PDFInfo
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- JP2021147525A JP2021147525A JP2020049495A JP2020049495A JP2021147525A JP 2021147525 A JP2021147525 A JP 2021147525A JP 2020049495 A JP2020049495 A JP 2020049495A JP 2020049495 A JP2020049495 A JP 2020049495A JP 2021147525 A JP2021147525 A JP 2021147525A
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- Prior art keywords
- acid
- fluidity improver
- compound
- thermoplastic resin
- polyester
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 229920005992 thermoplastic resin Polymers 0.000 title claims abstract description 78
- 239000000203 mixture Substances 0.000 title claims abstract description 44
- 239000011342 resin composition Substances 0.000 title claims abstract description 34
- 238000000465 moulding Methods 0.000 title abstract description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 180
- -1 ethyleneoxy groups Chemical group 0.000 claims abstract description 134
- 229920000642 polymer Polymers 0.000 claims abstract description 133
- 229920000728 polyester Polymers 0.000 claims abstract description 87
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract description 75
- 239000004593 Epoxy Substances 0.000 claims abstract description 69
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 66
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 58
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims abstract description 58
- 125000003700 epoxy group Chemical group 0.000 claims abstract description 53
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims abstract description 45
- 238000006243 chemical reaction Methods 0.000 claims abstract description 44
- 150000002009 diols Chemical class 0.000 claims abstract description 28
- 239000001384 succinic acid Substances 0.000 claims abstract description 27
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 80
- 239000003945 anionic surfactant Substances 0.000 claims description 26
- 238000002425 crystallisation Methods 0.000 claims description 24
- 230000008025 crystallization Effects 0.000 claims description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 23
- 239000002202 Polyethylene glycol Substances 0.000 claims description 16
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 claims description 16
- 229920001223 polyethylene glycol Polymers 0.000 claims description 16
- 239000004793 Polystyrene Substances 0.000 claims description 15
- 229920002223 polystyrene Polymers 0.000 claims description 15
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 14
- 229920005989 resin Polymers 0.000 claims description 14
- 239000011347 resin Substances 0.000 claims description 14
- 238000002156 mixing Methods 0.000 claims description 13
- 229920000570 polyether Polymers 0.000 claims description 13
- 229920005668 polycarbonate resin Polymers 0.000 claims description 10
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 9
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 claims description 5
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 claims description 5
- 239000004431 polycarbonate resin Substances 0.000 claims description 5
- 239000002253 acid Substances 0.000 description 51
- 238000004519 manufacturing process Methods 0.000 description 41
- 239000003963 antioxidant agent Substances 0.000 description 35
- 239000008188 pellet Substances 0.000 description 31
- 125000004432 carbon atom Chemical group C* 0.000 description 30
- 230000003078 antioxidant effect Effects 0.000 description 27
- 238000000034 method Methods 0.000 description 27
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 24
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 23
- 239000000463 material Substances 0.000 description 20
- 235000014113 dietary fatty acids Nutrition 0.000 description 19
- 239000000194 fatty acid Substances 0.000 description 19
- 229930195729 fatty acid Natural products 0.000 description 19
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 16
- 239000003063 flame retardant Substances 0.000 description 16
- 229910019142 PO4 Inorganic materials 0.000 description 15
- 150000004665 fatty acids Chemical class 0.000 description 15
- 239000000835 fiber Substances 0.000 description 15
- 235000021317 phosphate Nutrition 0.000 description 15
- 239000003153 chemical reaction reagent Substances 0.000 description 14
- 239000003795 chemical substances by application Substances 0.000 description 14
- 239000011777 magnesium Substances 0.000 description 14
- 229910052749 magnesium Inorganic materials 0.000 description 14
- 239000010452 phosphate Substances 0.000 description 14
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 14
- 239000011734 sodium Substances 0.000 description 14
- 229910052708 sodium Inorganic materials 0.000 description 14
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 14
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- 150000004985 diamines Chemical group 0.000 description 13
- 239000002023 wood Substances 0.000 description 13
- 229910052751 metal Inorganic materials 0.000 description 12
- 239000002184 metal Substances 0.000 description 12
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 12
- 239000007983 Tris buffer Substances 0.000 description 11
- 125000001931 aliphatic group Chemical group 0.000 description 11
- 125000003118 aryl group Chemical group 0.000 description 11
- XUCHXOAWJMEFLF-UHFFFAOYSA-N bisphenol F diglycidyl ether Chemical compound C1OC1COC(C=C1)=CC=C1CC(C=C1)=CC=C1OCC1CO1 XUCHXOAWJMEFLF-UHFFFAOYSA-N 0.000 description 11
- 239000011575 calcium Substances 0.000 description 11
- 229910052791 calcium Inorganic materials 0.000 description 11
- 229920001971 elastomer Polymers 0.000 description 11
- 150000002148 esters Chemical class 0.000 description 11
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 11
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 10
- OAJHWYJGCSAOTQ-UHFFFAOYSA-N [Zr].CCCCCCCCO.CCCCCCCCO.CCCCCCCCO.CCCCCCCCO Chemical compound [Zr].CCCCCCCCO.CCCCCCCCO.CCCCCCCCO.CCCCCCCCO OAJHWYJGCSAOTQ-UHFFFAOYSA-N 0.000 description 10
- 229920001577 copolymer Polymers 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- WRKCIHRWQZQBOL-UHFFFAOYSA-N octyl dihydrogen phosphate Chemical compound CCCCCCCCOP(O)(O)=O WRKCIHRWQZQBOL-UHFFFAOYSA-N 0.000 description 10
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 10
- 230000000379 polymerizing effect Effects 0.000 description 10
- 229910052700 potassium Inorganic materials 0.000 description 10
- 239000011591 potassium Substances 0.000 description 10
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 10
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 9
- 150000007513 acids Chemical class 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 9
- 229910052744 lithium Inorganic materials 0.000 description 9
- 239000012188 paraffin wax Substances 0.000 description 9
- 238000006116 polymerization reaction Methods 0.000 description 9
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 8
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 8
- 239000001361 adipic acid Substances 0.000 description 8
- 235000011037 adipic acid Nutrition 0.000 description 8
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 8
- 239000002608 ionic liquid Substances 0.000 description 8
- 239000000314 lubricant Substances 0.000 description 8
- 229910052698 phosphorus Inorganic materials 0.000 description 8
- 239000011574 phosphorus Substances 0.000 description 8
- 239000004014 plasticizer Substances 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 8
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 7
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 7
- 125000002723 alicyclic group Chemical group 0.000 description 7
- 229910052783 alkali metal Inorganic materials 0.000 description 7
- 239000003484 crystal nucleating agent Substances 0.000 description 7
- 239000000806 elastomer Substances 0.000 description 7
- 239000004417 polycarbonate Substances 0.000 description 7
- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 6
- FKKAGFLIPSSCHT-UHFFFAOYSA-N 1-dodecoxydodecane;sulfuric acid Chemical compound OS(O)(=O)=O.CCCCCCCCCCCCOCCCCCCCCCCCC FKKAGFLIPSSCHT-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- 239000004698 Polyethylene Substances 0.000 description 6
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 6
- 150000001768 cations Chemical class 0.000 description 6
- 238000005886 esterification reaction Methods 0.000 description 6
- XGIDNLGWAKKYQJ-UHFFFAOYSA-N icosyl dihydrogen phosphate Chemical compound CCCCCCCCCCCCCCCCCCCCOP(O)(O)=O XGIDNLGWAKKYQJ-UHFFFAOYSA-N 0.000 description 6
- 230000001771 impaired effect Effects 0.000 description 6
- 150000002500 ions Chemical class 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
- 239000004611 light stabiliser Substances 0.000 description 6
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 6
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 6
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 6
- 229920000573 polyethylene Polymers 0.000 description 6
- 239000000377 silicon dioxide Substances 0.000 description 6
- 150000005846 sugar alcohols Polymers 0.000 description 6
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 6
- 101100323621 Drosophila melanogaster Drip gene Proteins 0.000 description 5
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
- 239000004743 Polypropylene Substances 0.000 description 5
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 5
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 150000001450 anions Chemical class 0.000 description 5
- 125000001204 arachidyl 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])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])C([H])([H])[H] 0.000 description 5
- FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 description 5
- 239000000945 filler Substances 0.000 description 5
- 235000013312 flour Nutrition 0.000 description 5
- 239000011737 fluorine Substances 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 238000000691 measurement method Methods 0.000 description 5
- 229920003986 novolac Polymers 0.000 description 5
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
- 235000011007 phosphoric acid Nutrition 0.000 description 5
- 229920001155 polypropylene Polymers 0.000 description 5
- 239000012779 reinforcing material Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 5
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 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
- WXUAQHNMJWJLTG-UHFFFAOYSA-N 2-methylbutanedioic acid Chemical compound OC(=O)C(C)CC(O)=O WXUAQHNMJWJLTG-UHFFFAOYSA-N 0.000 description 4
- XJMMNTGIMDZPMU-UHFFFAOYSA-N 3-methylglutaric acid Chemical compound OC(=O)CC(C)CC(O)=O XJMMNTGIMDZPMU-UHFFFAOYSA-N 0.000 description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-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
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- 239000002841 Lewis acid Substances 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 229920000877 Melamine resin Polymers 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- 239000006057 Non-nutritive feed additive Substances 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 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 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
- 229910052796 boron Inorganic materials 0.000 description 4
- 239000004566 building material Substances 0.000 description 4
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 4
- 239000004927 clay Substances 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical class OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- 238000000113 differential scanning calorimetry Methods 0.000 description 4
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 4
- ZHQLTKAVLJKSKR-UHFFFAOYSA-N homophthalic acid Chemical compound OC(=O)CC1=CC=CC=C1C(O)=O ZHQLTKAVLJKSKR-UHFFFAOYSA-N 0.000 description 4
- 150000007517 lewis acids Chemical class 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 4
- 150000007522 mineralic acids Chemical class 0.000 description 4
- 239000002736 nonionic surfactant Substances 0.000 description 4
- 150000007524 organic acids Chemical class 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 239000002530 phenolic antioxidant Substances 0.000 description 4
- 239000005060 rubber Substances 0.000 description 4
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 150000003568 thioethers Chemical class 0.000 description 4
- 238000004448 titration Methods 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 3
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 3
- XWOVRWIRPYMVKK-UHFFFAOYSA-N 1-octadecoxyoctadecane;sulfuric acid Chemical compound OS(O)(=O)=O.CCCCCCCCCCCCCCCCCCOCCCCCCCCCCCCCCCCCC XWOVRWIRPYMVKK-UHFFFAOYSA-N 0.000 description 3
- 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 3
- BXGYYDRIMBPOMN-UHFFFAOYSA-N 2-(hydroxymethoxy)ethoxymethanol Chemical compound OCOCCOCO BXGYYDRIMBPOMN-UHFFFAOYSA-N 0.000 description 3
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- AVOVSJYQRZMDQJ-KVVVOXFISA-M lithium;(z)-octadec-9-enoate Chemical compound [Li+].CCCCCCCC\C=C/CCCCCCCC([O-])=O AVOVSJYQRZMDQJ-KVVVOXFISA-M 0.000 description 1
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- AZEPWULHRMVZQR-UHFFFAOYSA-M lithium;dodecanoate Chemical compound [Li+].CCCCCCCCCCCC([O-])=O AZEPWULHRMVZQR-UHFFFAOYSA-M 0.000 description 1
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- UPSGVQKYBQAFEJ-UHFFFAOYSA-M lithium;octadecyl sulfate Chemical compound [Li+].CCCCCCCCCCCCCCCCCCOS([O-])(=O)=O UPSGVQKYBQAFEJ-UHFFFAOYSA-M 0.000 description 1
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- PJJZFXPJNUVBMR-UHFFFAOYSA-L magnesium benzoate Chemical compound [Mg+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 PJJZFXPJNUVBMR-UHFFFAOYSA-L 0.000 description 1
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- GVALZJMUIHGIMD-UHFFFAOYSA-H magnesium phosphate Chemical compound [Mg+2].[Mg+2].[Mg+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O GVALZJMUIHGIMD-UHFFFAOYSA-H 0.000 description 1
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- OQXSVLMHUIVNRJ-UHFFFAOYSA-L magnesium;2-dodecylbenzenesulfonate Chemical compound [Mg+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OQXSVLMHUIVNRJ-UHFFFAOYSA-L 0.000 description 1
- BJZBHTNKDCBDNQ-UHFFFAOYSA-L magnesium;dodecanoate Chemical compound [Mg+2].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O BJZBHTNKDCBDNQ-UHFFFAOYSA-L 0.000 description 1
- HBNDBUATLJAUQM-UHFFFAOYSA-L magnesium;dodecyl sulfate Chemical compound [Mg+2].CCCCCCCCCCCCOS([O-])(=O)=O.CCCCCCCCCCCCOS([O-])(=O)=O HBNDBUATLJAUQM-UHFFFAOYSA-L 0.000 description 1
- YCOBGHKTLCKEJD-UHFFFAOYSA-L magnesium;hexadecyl sulfate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCOS([O-])(=O)=O.CCCCCCCCCCCCCCCCOS([O-])(=O)=O YCOBGHKTLCKEJD-UHFFFAOYSA-L 0.000 description 1
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- BOQSSGDQNWEFSX-UHFFFAOYSA-N propan-2-yl 2-methylprop-2-enoate Chemical compound CC(C)OC(=O)C(C)=C BOQSSGDQNWEFSX-UHFFFAOYSA-N 0.000 description 1
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- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
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- 230000002787 reinforcement Effects 0.000 description 1
- GDESWOTWNNGOMW-UHFFFAOYSA-N resorcinol monobenzoate Chemical compound OC1=CC=CC(OC(=O)C=2C=CC=CC=2)=C1 GDESWOTWNNGOMW-UHFFFAOYSA-N 0.000 description 1
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- 238000007142 ring opening reaction Methods 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
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- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
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- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
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- 239000002893 slag Substances 0.000 description 1
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- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
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- BYKRNSHANADUFY-UHFFFAOYSA-M sodium octanoate Chemical compound [Na+].CCCCCCCC([O-])=O BYKRNSHANADUFY-UHFFFAOYSA-M 0.000 description 1
- 229940067741 sodium octyl sulfate Drugs 0.000 description 1
- 229960004025 sodium salicylate Drugs 0.000 description 1
- ZDQYSKICYIVCPN-UHFFFAOYSA-L sodium succinate (anhydrous) Chemical compound [Na+].[Na+].[O-]C(=O)CCC([O-])=O ZDQYSKICYIVCPN-UHFFFAOYSA-L 0.000 description 1
- ZQOXGRIKWKXDIJ-UHFFFAOYSA-M sodium;1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F ZQOXGRIKWKXDIJ-UHFFFAOYSA-M 0.000 description 1
- PFIOPNYSBSJFJJ-UHFFFAOYSA-M sodium;2-octylbenzenesulfonate Chemical compound [Na+].CCCCCCCCC1=CC=CC=C1S([O-])(=O)=O PFIOPNYSBSJFJJ-UHFFFAOYSA-M 0.000 description 1
- XTIVBOWLUYDHKE-UHFFFAOYSA-M sodium;cyclohexanecarboxylate Chemical compound [Na+].[O-]C(=O)C1CCCCC1 XTIVBOWLUYDHKE-UHFFFAOYSA-M 0.000 description 1
- DAJSVUQLFFJUSX-UHFFFAOYSA-M sodium;dodecane-1-sulfonate Chemical compound [Na+].CCCCCCCCCCCCS([O-])(=O)=O DAJSVUQLFFJUSX-UHFFFAOYSA-M 0.000 description 1
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- 230000002194 synthesizing effect Effects 0.000 description 1
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- YRGLXIVYESZPLQ-UHFFFAOYSA-I tantalum pentafluoride Chemical compound F[Ta](F)(F)(F)F YRGLXIVYESZPLQ-UHFFFAOYSA-I 0.000 description 1
- 229920006027 ternary co-polymer Polymers 0.000 description 1
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
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- NZNAAUDJKMURFU-UHFFFAOYSA-N tetrakis(2,2,6,6-tetramethylpiperidin-4-yl) butane-1,2,3,4-tetracarboxylate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)CC(C(=O)OC1CC(C)(C)NC(C)(C)C1)C(C(=O)OC1CC(C)(C)NC(C)(C)C1)CC(=O)OC1CC(C)(C)NC(C)(C)C1 NZNAAUDJKMURFU-UHFFFAOYSA-N 0.000 description 1
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- KEROTHRUZYBWCY-UHFFFAOYSA-N tridecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCOC(=O)C(C)=C KEROTHRUZYBWCY-UHFFFAOYSA-N 0.000 description 1
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- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- WTLBZVNBAKMVDP-UHFFFAOYSA-N tris(2-butoxyethyl) phosphate Chemical compound CCCCOCCOP(=O)(OCCOCCCC)OCCOCCCC WTLBZVNBAKMVDP-UHFFFAOYSA-N 0.000 description 1
- LIPMRGQQBZJCTM-UHFFFAOYSA-N tris(2-propan-2-ylphenyl) phosphate Chemical compound CC(C)C1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C(C)C)OC1=CC=CC=C1C(C)C LIPMRGQQBZJCTM-UHFFFAOYSA-N 0.000 description 1
- QQBLOZGVRHAYGT-UHFFFAOYSA-N tris-decyl phosphite Chemical compound CCCCCCCCCCOP(OCCCCCCCCCC)OCCCCCCCCCC QQBLOZGVRHAYGT-UHFFFAOYSA-N 0.000 description 1
- KPGXUAIFQMJJFB-UHFFFAOYSA-H tungsten hexachloride Chemical compound Cl[W](Cl)(Cl)(Cl)(Cl)Cl KPGXUAIFQMJJFB-UHFFFAOYSA-H 0.000 description 1
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- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
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- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 1
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Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Polyesters Or Polycarbonates (AREA)
Abstract
Description
前記ジオール(a1)が、1,4−ブタンジオール、またはエチレングリコールの少なくとも一方であり、前記ジカルボン酸(a2)が、コハク酸、またはコハク酸を含有するジカルボン酸の混合物であることを特徴とするものである。
前記ポリエステル(a)の末端に有する水酸基またはカルボキシル基と、化合物(b)の末端に有する水酸基と、前記エポキシ化合物(D)のエポキシ基またはエポキシ基が反応することによって形成された水酸基との反応により形成された、エステル結合またはエーテル結合を介して結合してなる構造を有することが好ましい。また、本発明の流動性向上剤は、前記高分子化合物(E)が、前記ポリエステルのブロック(A)と、前記ポリエーテルのブロック(B)と、がエステル結合を介して繰り返し交互に結合してなる両末端にカルボキシル基を有するブロックポリマー(C)と、前記エポキシ化合物(D)と、がエステル結合を介して結合してなる構造を有することが好ましい。さらに、本発明の流動性向上剤は、前記ポリエステル(a)が、両末端にカルボキシル基を有する構造であることが好ましい。さらにまた、本発明の流動性向上剤は、前記化合物(b)が、ポリエチレングリコールであることが好ましい。また、本発明の流動性向上剤は、前記高分子化合物(E)の結晶化温度が20〜70℃の範囲内であることが好ましい。さらに、本発明の流動性向上剤は、前記ポリエステル(a)の数平均分子量が、ポリスチレン換算で1,000〜10,000であることが好ましい。さらにまた、本発明の流動性向上剤は、前記ブロックポリマー(C)の数平均分子量がポリスチレン換算で5,000〜50,000であることが好ましい。
本発明の流動性向上剤は、ジオール(a1)とジカルボン酸(a2)が反応して得られるポリエステル(a)と、エチレンオキシ基を一つ以上有する両末端に水酸基を有する化合物(b)と、エポキシ基を2個以上有するエポキシ化合物(D)と、が反応して得られる高分子化合物(E)の1種以上を含有するものである。ここで、エチレンオキシ基とは、下記一般式(1)で示される基である。
下記水酸基価測定方法で水酸基価を測定し、下記式で数平均分子量(以下「Mn」とも称する)を決定した。
数平均分子量=(56110×2)/水酸基価
<水酸基価測定法>
・試薬A(アセチル化剤)
(1)トリエチルホスフェート 1560mL
(2)無水酢酸 193mL
(3)過塩素酸(60%) 16g
上記試薬を(1)→(2)→(3)の順に混合する。
・試薬B
ピリジンと純水を体積比率で3:1に混合する。
・試薬C
500mLのイソプロピルアルコールにフェノールフタレイン液を2〜3滴加え、1N−KOH水溶液で中性にする。
水酸基価[mgKOH/g]=56.11×f×(T−B)/S
f:1N−KOH水溶液のfactor
B:空試験滴定量[mL]
T:本試験滴定量[mL]
S:サンプル量[g]
数平均分子量(以下、「Mn」とも称する)は、ゲルパーミエーションクロマトグラフィー(GPC)法によって測定した。Mnの測定条件は以下の通りである。
装置 :日本分光(株)製GPC装置
溶媒 :クロロホルム
基準物質 :ポリスチレン
検出器 :示差屈折計(RI検出器)
カラム固定相:昭和電工(株)製Shodex LF−804
カラム温度 :40℃
サンプル濃度:1mg/1mL
流量 :0.8mL/min.
注入量 :100μL
結晶化温度は示差走査熱量測定器(DSC)を用いて測定する。試料を、アルミニウムパンに3±1mg量り取り、室温(25℃)から10℃/分の速度で130℃まで昇温し、5分間保持後、10℃/分の速度で0℃まで冷却して得られたチャートにおいて、吸熱のピークトップとなる温度を結晶化温度とする。
本発明の流動性向上剤組成物は、本発明の流動性向上剤に対し、さらに、アニオン性界面活性剤の1種以上が配合されてなるものである。
本発明の熱可塑性樹脂組成物は、熱可塑性樹脂に対し、本発明の流動性向上剤、または本発明の流動性向上剤組成物が配合されてなるものである。
炭素原子数5〜15のものが挙げられ、例えば、1,2,3,4−テトラメチルイミダゾリニウム、1,3−ジメチルイミダゾリニウム;
炭素原子数5〜15のものが挙げられ、例えば、1,3−ジメチルイミダゾリウム、1−エチル−3−メチルイミダゾリウム;
炭素原子数6〜15のものが挙げられ、例えば、1,3−ジメチル−1,4,5,6−テトラヒドロピリミジニウム、1,2,3,4−テトラメチル−1,4,5,6−テトラヒドロピリミジニウム;
炭素原子数6〜20のものが挙げられ、例えば、1,3−ジメチル−1,4−ジヒドロピリミジニウム、1,3−ジメチル−1,6−ジヒドロピリミジニウム、8−メチル−1,8−ジアザビシクロ[5,4,0]−7,9−ウンデカジエニウム、8−メチル−1,8−ジアザビシクロ[5,4,0]−7,10−ウンデカジエニウム。
炭素原子数8〜15のものが挙げられ、例えば、2−ジメチルアミノ−1,3,4−トリメチルイミダゾリニウム、2−ジエチルアミノ−1,3,4−トリメチルイミダゾリニウム;
炭素原子数8〜15のものが挙げられ、例えば、2−ジメチルアミノ−1,3,4−トリメチルイミダゾリウム、2−ジエチルアミノ−1,3,4−トリメチルイミダゾリウム;
炭素原子数10〜20のものが挙げられ、例えば、2−ジメチルアミノ−1,3,4−トリメチル−1,4,5,6−テトラヒドロピリミジニウム、2−ジエチルアミノ−1,3−ジメチル−4−エチル−1,4,5,6−テトラヒドロピリミジニウム;
炭素原子数10〜20のものが挙げられ、例えば、2−ジメチルアミノ−1,3,4−トリメチル−1,4−ジヒドロピリミジニウム、2−ジメチルアミノ−1,3,4−トリメチル−1,6−ジヒドロピリミジニウム、2−ジエチルアミノ−1,3−ジメチル−4−エチル−1,4−ジヒドロピリミジニウム、2−ジエチルアミノ−1,3−ジメチル−4−エチル−1,6−ジヒドロピリミジニウム。
下記の製造例に従い、本発明の流動性向上剤である高分子化合物(E)を製造した。また、下記の製造例において、化合物(b)の数平均分子量は、下記<水酸基価からの数平均分子量の算出方法>で算出し、化合物(b)以外の数平均分子量は、下記<ポリスチレン換算による数平均分子量の測定方法>で算出した。
下記水酸基価測定方法で水酸基価を測定し、下記式で数平均分子量を決定した。
数平均分子量=(56110×2)/水酸基価
<水酸基価測定法>
・試薬A(アセチル化剤)
(1)トリエチルホスフェート 1560mL
(2)無水酢酸 193mL
(3)過塩素酸(60%) 16g
上記試薬を(1)→(2)→(3)の順に混合する。
・試薬B
ピリジンと純水を体積比率で3:1に混合する。
・試薬C
500mLのイソプロピルアルコールにフェノールフタレイン液を2〜3滴加え、1N−KOH水溶液で中性にする。
水酸基価[mgKOH/g]=56.11×f×(T−B)/S
f:1N−KOH水溶液のfactor
B:空試験滴定量[mL]
T:本試験滴定量[mL]
S:サンプル量[g]
数平均分子量は、ゲルパーミエーションクロマトグラフィー(GPC)法によって測定した。Mnの測定条件は以下の通りである。
装置 :日本分光(株)製GPC装置
溶媒 :クロロホルム
基準物質 :ポリスチレン
検出器 :示差屈折計(RI検出器)
カラム固定相:昭和電工(株)製Shodex LF−804
カラム温度 :40℃
サンプル濃度:1mg/1mL
流量 :0.8mL/min.
注入量 :100μL
セパラブルフラスコ中で、酸化防止剤(テトラキス[3−(3,5−ジ第三ブチル−4−ヒドロキシフェニル)プロピオニルオキシメチル]メタン、アデカスタブAO−60(株)ADEKA製)0.2g存在下、1,4−ブタンジオール122g(1.35モル)と、コハク酸168g(1.42モル)を、140℃から190℃まで徐々に昇温しながら常圧で3時間重合して、ポリエステル(a)−1を得た。得られたポリエステル(a)−1の数平均分子量は3,000であった。
示差走査熱量測定器(Perkin社製Diamond DSC)を用いて結晶化温度を測定する。試料を、ペレットを細かく切断し、アルミニウムパンに3±1mg量り取り、室温(25℃)から10℃/分の速度で130℃まで昇温し、5分間保持後、10℃/分の速度で0℃まで冷却して得られたチャートにおいて、吸熱のピークトップとなる温度を結晶化温度とした。
製造例1と同様にして得られたブロックポリマー(C)−1の400gに、エポキシ基を2個以上有するエポキシ化合物(D)−2として、水素添加ビスフェノールAジグリシジルエーテル(エポキシ当量215g/eq)4gを仕込み、220℃で5時間、減圧下で重合した後、製造例1と同様にして、本発明の流動性向上剤である高分子化合物(E)−2のペレットを400g得た。得られた高分子化合物(E)−2のペレットを、製造例1と同様にして、結晶化温度を測定した。結果を表1に示す。
製造例1と同様にして得られたブロックポリマー(C)−1の400gに、エポキシ基を2個以上有するエポキシ化合物(D)−3として、ジシクロペンタジエンジメタノールジグリシジルエーテル(エポキシ当量170g/eq)3gを仕込み、220℃で5時間、減圧下で重合した後、製造例1と同様にして、本発明の流動性向上剤である高分子化合物(E)−3のペレットを400g得た。得られた高分子化合物(E)−3のペレットを、製造例1と同様にして、結晶化温度を測定した。
セパラブルフラスコ中で、酸化防止剤(テトラキス[3−(3,5−ジ第三ブチル−4−ヒドロキシフェニル)プロピオニルオキシメチル]メタン、アデカスタブAO−60(株)ADEKA製)0.2g存在下、1,4−ブタンジオール58g(0.65モル)と、コハク酸91g(0.77モル)を、140℃から190℃まで徐々に昇温しながら常圧で3時間重合して、ポリエステル(a)−2を得た。得られたポリエステル(a)−2の数平均分子量は1,000であった。
セパラブルフラスコ中で、酸化防止剤(テトラキス[3−(3,5−ジ第三ブチル−4−ヒドロキシフェニル)プロピオニルオキシメチル]メタン、アデカスタブAO−60(株)ADEKA製)0.2g存在下、エチレングリコール100g(1.61モル)と、コハク酸199g(1.69モル)を、140℃から190℃まで徐々に昇温しながら常圧で3時間重合して、ポリエステル(a)−3を得た。得られたポリエステル(a)−3の数平均分子量は3,000であった。
セパラブルフラスコ中で、酸化防止剤(テトラキス[3−(3,5−ジ第三ブチル−4−ヒドロキシフェニル)プロピオニルオキシメチル]メタン、アデカスタブAO−60(株)ADEKA製)0.2g存在下、1,4−ブタンジオール101g(1.12モル)と、エチレングリコール17g(0.28モル)と、コハク酸173g(1.47モル)を、140℃から190℃まで徐々に昇温しながら常圧で3時間重合して、ポリエステル(a)−4を得た。得られたポリエステル(a)−4の数平均分子量は3,000であった。
セパラブルフラスコ中で、酸化防止剤(テトラキス[3−(3,5−ジ第三ブチル−4−ヒドロキシフェニル)プロピオニルオキシメチル]メタン、アデカスタブAO−60(株)ADEKA製)0.2g存在下、1,4−ブタンジオール120g(1.33モル)と、コハク酸149g(1.26モル)と、アジピン酸21g(0.14モル)を、140℃から190℃まで徐々に昇温しながら常圧で3時間重合して、ポリエステル(a)−5を得た。得られたポリエステル(a)−5の数平均分子量は3,000であった。
セパラブルフラスコ中で、酸化防止剤(テトラキス[3−(3,5−ジ第三ブチル−4−ヒドロキシフェニル)プロピオニルオキシメチル]メタン、アデカスタブAO−60(株)ADEKA製)0.2g存在下、1,4−ブタンジオール118g(1.31モル)と、コハク酸130g(1.10モル)と、アジピン酸40g(0.28モル)を、140℃から190℃まで徐々に昇温しながら常圧で3時間重合して、ポリエステル(a)−6を得た。得られたポリエステル(a)−6の数平均分子量は3,000であった。
セパラブルフラスコ中で、酸化防止剤(テトラキス[3−(3,5−ジ第三ブチル−4−ヒドロキシフェニル)プロピオニルオキシメチル]メタン、アデカスタブAO−60(株)ADEKA製)0.2g存在下、1,4−ブタンジオール116g(1.28モル)と、コハク酸144g(1.22モル)と、セバシン酸27g(0.14モル)を、140℃から190℃まで徐々に昇温しながら常圧で3時間重合して、ポリエステル(a)−7を得た。得られたポリエステル(a)−7の数平均分子量は3,000であった。
セパラブルフラスコ中で、酸化防止剤(テトラキス[3−(3,5−ジ第三ブチル−4−ヒドロキシフェニル)プロピオニルオキシメチル]メタン、アデカスタブAO−60(株)ADEKA製)0.2g存在下、1,4−ブタンジオール110g(1.22モル)と、コハク酸122g(1.04モル)と、セバシン酸52g(0.26モル)を、140℃から190℃まで徐々に昇温しながら常圧で3時間重合して、ポリエステル(a)−8を得た。得られたポリエステル(a)−8の数平均分子量は3,000であった。
セパラブルフラスコ中で、酸化防止剤(テトラキス[3−(3,5−ジ第三ブチル−4−ヒドロキシフェニル)プロピオニルオキシメチル]メタン、アデカスタブAO−60(株)ADEKA製)0.2g存在下、1,4−ブタンジオール105g(1.17モル)と、コハク酸103g(0.87モル)と、セバシン酸75g(0.37モル)を、140℃から190℃まで徐々に昇温しながら常圧で3時間重合して、ポリエステル(a)−9を得た。得られたポリエステル(a)−9の数平均分子量は3,000であった。
セパラブルフラスコ中で、酸化防止剤(テトラキス[3−(3,5−ジ第三ブチル−4−ヒドロキシフェニル)プロピオニルオキシメチル]メタン、アデカスタブAO−60(株)ADEKA製)0.2g存在下、1,4−ブタンジオール115g(1.27モル)と、コハク酸143g(1.21モル)と、2,6−ナフタレンジカルボン酸29g(0.13モル)を、140℃から190℃まで徐々に昇温しながら常圧で3時間重合して、ポリエステル(a)−10を得た。得られたポリエステル(a)−10の数平均分子量は3,000であった。
下記の表1〜8に記載した配合量(質量部)に基づいてブレンドした熱可塑性樹脂組成物を、(株)池貝製2軸押出機(PCM30,60mesh入り)を用いて、230℃、6kg/時間の条件で造粒し、ペレットを得た。得られたペレットを用いて、下記測定方法でメルトフローレートを測定し、流動性の評価を行った。結果を表1〜8に示す。同様にして、下記の表4、8に示す配合で、比較例の熱可塑性樹脂組成物を調製し、評価を行った。結果を表4、8に示す。
立山科学工業(株)製メルトインデクサL227−41を用いて、ISO1133に準拠して測定した。ただし、表5〜8記載のポリカーボネート/ABS樹脂組成物については、260℃×5.00kgで測定した。
Claims (13)
- ジオール(a1)とジカルボン酸(a2)が反応して得られるポリエステル(a)と、エチレンオキシ基を一つ以上有する両末端に水酸基を有する化合物(b)と、エポキシ基を2個以上有するエポキシ化合物(D)と、が反応して得られる高分子化合物(E)の1種以上を含有する流動性向上剤であって、
前記ジオール(a1)が、1,4−ブタンジオール、またはエチレングリコールの少なくとも一方であり、前記ジカルボン酸(a2)が、コハク酸、またはコハク酸を含有するジカルボン酸の混合物であることを特徴とする流動性向上剤。 - 前記高分子化合物(E)が、前記ポリエステル(a)から構成されるポリエステルのブロック(A)と、前記化合物(b)から構成されるポリエーテルのブロック(B)とを有し、
前記ポリエステル(a)の末端に有する水酸基またはカルボキシル基と、化合物(b)の末端に有する水酸基と、前記エポキシ化合物(D)のエポキシ基またはエポキシ基が反応することによって形成された水酸基との反応により形成された、エステル結合またはエーテル結合を介して結合してなる構造を有する請求項1記載の流動性向上剤。 - 前記高分子化合物(E)が、前記ポリエステルのブロック(A)と、前記ポリエーテルのブロック(B)と、がエステル結合を介して繰り返し交互に結合してなる両末端にカルボキシル基を有するブロックポリマー(C)と、前記エポキシ化合物(D)と、がエステル結合を介して結合してなる構造を有する請求項2記載の流動性向上剤。
- 前記ポリエステル(a)が、両末端にカルボキシル基を有する構造である請求項1〜3のうちいずれか一項記載の流動性向上剤。
- 前記化合物(b)が、ポリエチレングリコールである請求項1〜4のうちいずれか一項記載の流動性向上剤。
- 前記高分子化合物(E)の結晶化温度が20〜70℃の範囲内である請求項1〜5のうちいずれか一項記載の流動性向上剤。
- 前記ポリエステル(a)の数平均分子量が、ポリスチレン換算で1,000〜10,000である請求項1〜6のうちいずれか一項記載の流動性向上剤。
- 前記ブロックポリマー(C)の数平均分子量がポリスチレン換算で5,000〜50,000である請求項3〜7のうちいずれか一項記載の流動性向上剤。
- 請求項1〜8のうちいずれか1項記載の流動性向上剤に対し、さらにアニオン性界面活性剤が配合されていることを特徴とする流動性向上剤組成物。
- 熱可塑性樹脂に対し、請求項1〜8のうちいずれか一項記載の流動性向上剤が配合されていることを特徴とする熱可塑性樹脂組成物。
- 熱可塑性樹脂に対し、請求項9記載の流動性向上剤組成物が配合されていることを特徴とする熱可塑性樹脂組成物。
- 前記熱可塑性樹脂が、ポリカーボネート樹脂およびアクリロニトリル−ブタジエン−スチレン樹脂からなる群から選ばれる1種以上である請求項10または11記載の熱可塑性樹脂組成物。
- 請求項10〜12のうちいずれか一項記載の熱可塑性樹脂組成物からなることを特徴とする成形体。
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