JPWO2014057766A1 - ポリ乳酸樹脂組成物、成形体およびポリ乳酸樹脂組成物の製造方法 - Google Patents
ポリ乳酸樹脂組成物、成形体およびポリ乳酸樹脂組成物の製造方法 Download PDFInfo
- Publication number
- JPWO2014057766A1 JPWO2014057766A1 JP2013543449A JP2013543449A JPWO2014057766A1 JP WO2014057766 A1 JPWO2014057766 A1 JP WO2014057766A1 JP 2013543449 A JP2013543449 A JP 2013543449A JP 2013543449 A JP2013543449 A JP 2013543449A JP WO2014057766 A1 JPWO2014057766 A1 JP WO2014057766A1
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- Prior art keywords
- poly
- lactic acid
- polylactic acid
- acid
- average molecular
- 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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- 239000011342 resin composition Substances 0.000 title claims abstract description 101
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- 229940022769 d- lactic acid Drugs 0.000 claims abstract description 292
- 229920001432 poly(L-lactide) Polymers 0.000 claims abstract description 283
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- 239000011347 resin Substances 0.000 claims abstract description 89
- 238000000113 differential scanning calorimetry Methods 0.000 claims abstract description 24
- 229910001463 metal phosphate Inorganic materials 0.000 claims abstract description 21
- 238000001816 cooling Methods 0.000 claims abstract description 11
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 7
- 150000001340 alkali metals Chemical group 0.000 claims abstract description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 5
- 150000001342 alkaline earth metals Chemical group 0.000 claims abstract description 5
- 238000002844 melting Methods 0.000 claims description 216
- 230000008018 melting Effects 0.000 claims description 214
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- 238000004898 kneading Methods 0.000 claims description 57
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- 235000019799 monosodium phosphate Nutrition 0.000 claims description 8
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical group [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 claims description 8
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- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 claims description 5
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- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 claims description 5
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- YYRMJZQKEFZXMX-UHFFFAOYSA-L calcium bis(dihydrogenphosphate) Chemical compound [Ca+2].OP(O)([O-])=O.OP(O)([O-])=O YYRMJZQKEFZXMX-UHFFFAOYSA-L 0.000 claims description 4
- 229940062672 calcium dihydrogen phosphate Drugs 0.000 claims description 4
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- YXXXKCDYKKSZHL-UHFFFAOYSA-M dipotassium;dioxido(oxo)phosphanium Chemical compound [K+].[K+].[O-][P+]([O-])=O YXXXKCDYKKSZHL-UHFFFAOYSA-M 0.000 claims description 4
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 claims description 4
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- 239000001257 hydrogen Substances 0.000 claims description 4
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- 235000019700 dicalcium phosphate Nutrition 0.000 claims description 2
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- ANBFRLKBEIFNQU-UHFFFAOYSA-M potassium;octadecanoate Chemical compound [K+].CCCCCCCCCCCCCCCCCC([O-])=O ANBFRLKBEIFNQU-UHFFFAOYSA-M 0.000 description 1
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- WQKGAJDYBZOFSR-UHFFFAOYSA-N potassium;propan-2-olate Chemical compound [K+].CC(C)[O-] WQKGAJDYBZOFSR-UHFFFAOYSA-N 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
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- HJCRVWSKQNDSPZ-UHFFFAOYSA-N propan-2-olate;samarium(3+) Chemical compound [Sm+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] HJCRVWSKQNDSPZ-UHFFFAOYSA-N 0.000 description 1
- PYLIDHFYDYRZSC-UHFFFAOYSA-N propan-2-olate;yttrium(3+) Chemical compound [Y+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] PYLIDHFYDYRZSC-UHFFFAOYSA-N 0.000 description 1
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- AABBHSMFGKYLKE-SNAWJCMRSA-N propan-2-yl (e)-but-2-enoate Chemical compound C\C=C\C(=O)OC(C)C AABBHSMFGKYLKE-SNAWJCMRSA-N 0.000 description 1
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- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- BHXBZLPMVFUQBQ-UHFFFAOYSA-K samarium(iii) chloride Chemical compound Cl[Sm](Cl)Cl BHXBZLPMVFUQBQ-UHFFFAOYSA-K 0.000 description 1
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- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
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- GROMGGTZECPEKN-UHFFFAOYSA-N sodium metatitanate Chemical compound [Na+].[Na+].[O-][Ti](=O)O[Ti](=O)O[Ti]([O-])=O GROMGGTZECPEKN-UHFFFAOYSA-N 0.000 description 1
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- 125000004079 stearyl 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])[H] 0.000 description 1
- 229910000018 strontium carbonate Inorganic materials 0.000 description 1
- UUCCCPNEFXQJEL-UHFFFAOYSA-L strontium dihydroxide Chemical compound [OH-].[OH-].[Sr+2] UUCCCPNEFXQJEL-UHFFFAOYSA-L 0.000 description 1
- 229910001866 strontium hydroxide Inorganic materials 0.000 description 1
- VEALVRVVWBQVSL-UHFFFAOYSA-N strontium titanate Chemical compound [Sr+2].[O-][Ti]([O-])=O VEALVRVVWBQVSL-UHFFFAOYSA-N 0.000 description 1
- RXSHXLOMRZJCLB-UHFFFAOYSA-L strontium;diacetate Chemical compound [Sr+2].CC([O-])=O.CC([O-])=O RXSHXLOMRZJCLB-UHFFFAOYSA-L 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical compound O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 1
- 229950000244 sulfanilic acid Drugs 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 1
- 229920001897 terpolymer Polymers 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
- 150000003512 tertiary amines Chemical class 0.000 description 1
- PKLMYPSYVKAPOX-UHFFFAOYSA-N tetra(propan-2-yloxy)germane Chemical compound CC(C)O[Ge](OC(C)C)(OC(C)C)OC(C)C PKLMYPSYVKAPOX-UHFFFAOYSA-N 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 1
- AFCAKJKUYFLYFK-UHFFFAOYSA-N tetrabutyltin Chemical compound CCCC[Sn](CCCC)(CCCC)CCCC AFCAKJKUYFLYFK-UHFFFAOYSA-N 0.000 description 1
- FSMKMWWGFZFPOZ-UHFFFAOYSA-L tetradecanoate;tin(2+) Chemical compound [Sn+2].CCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCC([O-])=O FSMKMWWGFZFPOZ-UHFFFAOYSA-L 0.000 description 1
- YMBCJWGVCUEGHA-UHFFFAOYSA-M tetraethylammonium chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC YMBCJWGVCUEGHA-UHFFFAOYSA-M 0.000 description 1
- RWWNQEOPUOCKGR-UHFFFAOYSA-N tetraethyltin Chemical compound CC[Sn](CC)(CC)CC RWWNQEOPUOCKGR-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- ZTXFOCMYRCGSMU-UHFFFAOYSA-M tetramethylphosphanium;bromide Chemical compound [Br-].C[P+](C)(C)C ZTXFOCMYRCGSMU-UHFFFAOYSA-M 0.000 description 1
- BRKFQVAOMSWFDU-UHFFFAOYSA-M tetraphenylphosphanium;bromide Chemical compound [Br-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BRKFQVAOMSWFDU-UHFFFAOYSA-M 0.000 description 1
- CRHIAMBJMSSNNM-UHFFFAOYSA-N tetraphenylstannane Chemical compound C1=CC=CC=C1[Sn](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 CRHIAMBJMSSNNM-UHFFFAOYSA-N 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- FAKFSJNVVCGEEI-UHFFFAOYSA-J tin(4+);disulfate Chemical compound [Sn+4].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O FAKFSJNVVCGEEI-UHFFFAOYSA-J 0.000 description 1
- LLVONELOQJAYBZ-UHFFFAOYSA-N tin(ii) phthalocyanine Chemical compound N1=C(C2=CC=CC=C2C2=NC=3C4=CC=CC=C4C(=N4)N=3)N2[Sn]N2C4=C(C=CC=C3)C3=C2N=C2C3=CC=CC=C3C1=N2 LLVONELOQJAYBZ-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- KLORKMOYYIOYOT-UHFFFAOYSA-K titanium(3+);triacetate Chemical compound [Ti+3].CC([O-])=O.CC([O-])=O.CC([O-])=O KLORKMOYYIOYOT-UHFFFAOYSA-K 0.000 description 1
- GPMKKHIGAJLBMZ-UHFFFAOYSA-J titanium(4+);tetraacetate Chemical compound [Ti+4].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O GPMKKHIGAJLBMZ-UHFFFAOYSA-J 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 229960001727 tretinoin Drugs 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- BDIWFCKBPZPBQT-UHFFFAOYSA-N tributyl(tributylstannylsulfanyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)S[Sn](CCCC)(CCCC)CCCC BDIWFCKBPZPBQT-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
- PWBHRVGYSMBMIO-UHFFFAOYSA-M tributylstannanylium;acetate Chemical compound CCCC[Sn](CCCC)(CCCC)OC(C)=O PWBHRVGYSMBMIO-UHFFFAOYSA-M 0.000 description 1
- XEPUJTDDAPFGMG-UHFFFAOYSA-L tributylstannanylium;sulfate Chemical compound CCCC[Sn](CCCC)(CCCC)OS(=O)(=O)O[Sn](CCCC)(CCCC)CCCC XEPUJTDDAPFGMG-UHFFFAOYSA-L 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- UDBAOKKMUMKEGZ-UHFFFAOYSA-K trichloromanganese Chemical compound [Cl-].[Cl-].[Cl-].[Mn+3] UDBAOKKMUMKEGZ-UHFFFAOYSA-K 0.000 description 1
- VYGSFTVYZHNGBU-UHFFFAOYSA-N trichloromethanesulfonic acid Chemical compound OS(=O)(=O)C(Cl)(Cl)Cl VYGSFTVYZHNGBU-UHFFFAOYSA-N 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- OLBXOAKEHMWSOV-UHFFFAOYSA-N triethyltin;hydrate Chemical compound O.CC[Sn](CC)CC OLBXOAKEHMWSOV-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- RMZAYIKUYWXQPB-UHFFFAOYSA-N trioctylphosphane Chemical compound CCCCCCCCP(CCCCCCCC)CCCCCCCC RMZAYIKUYWXQPB-UHFFFAOYSA-N 0.000 description 1
- 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
- HYPTXUAFIRUIRD-UHFFFAOYSA-N tripropan-2-yl stiborite Chemical compound [Sb+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] HYPTXUAFIRUIRD-UHFFFAOYSA-N 0.000 description 1
- KOWVWXQNQNCRRS-UHFFFAOYSA-N tris(2,4-dimethylphenyl) phosphate Chemical compound CC1=CC(C)=CC=C1OP(=O)(OC=1C(=CC(C)=CC=1)C)OC1=CC=C(C)C=C1C KOWVWXQNQNCRRS-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
- DOOPOMANTWCTIB-UHFFFAOYSA-M tris(2-methylpropyl)stannanylium;acetate Chemical compound CC([O-])=O.CC(C)C[Sn+](CC(C)C)CC(C)C DOOPOMANTWCTIB-UHFFFAOYSA-M 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 238000007666 vacuum forming Methods 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 239000010456 wollastonite Substances 0.000 description 1
- 229910052882 wollastonite Inorganic materials 0.000 description 1
- 229910000347 yttrium sulfate Inorganic materials 0.000 description 1
- JUWHRRAPBUAYTA-UHFFFAOYSA-K yttrium(3+);triacetate Chemical compound [Y+3].CC([O-])=O.CC([O-])=O.CC([O-])=O JUWHRRAPBUAYTA-UHFFFAOYSA-K 0.000 description 1
- QVOIJBIQBYRBCF-UHFFFAOYSA-H yttrium(3+);tricarbonate Chemical compound [Y+3].[Y+3].[O-]C([O-])=O.[O-]C([O-])=O.[O-]C([O-])=O QVOIJBIQBYRBCF-UHFFFAOYSA-H 0.000 description 1
- RTAYJOCWVUTQHB-UHFFFAOYSA-H yttrium(3+);trisulfate Chemical compound [Y+3].[Y+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O RTAYJOCWVUTQHB-UHFFFAOYSA-H 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- 239000011667 zinc carbonate Substances 0.000 description 1
- 235000004416 zinc carbonate Nutrition 0.000 description 1
- 229910000010 zinc carbonate Inorganic materials 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- 150000003755 zirconium compounds Chemical class 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
- ZXAUZSQITFJWPS-UHFFFAOYSA-J zirconium(4+);disulfate Chemical compound [Zr+4].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O ZXAUZSQITFJWPS-UHFFFAOYSA-J 0.000 description 1
- PFXYQVJESZAMSV-UHFFFAOYSA-K zirconium(iii) chloride Chemical compound Cl[Zr](Cl)Cl PFXYQVJESZAMSV-UHFFFAOYSA-K 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/32—Phosphorus-containing compounds
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/06—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/04—Polyesters derived from hydroxycarboxylic acids, e.g. lactones
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/32—Phosphorus-containing compounds
- C08K2003/321—Phosphates
- C08K2003/324—Alkali metal phosphate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/32—Phosphorus-containing compounds
- C08K2003/321—Phosphates
- C08K2003/325—Calcium, strontium or barium phosphate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
- C08L101/16—Compositions of unspecified macromolecular compounds the macromolecular compounds being biodegradable
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
Abstract
Description
MxHyPOz (1)
(一般式(1)において、Mはアルカリ金属原子またはアルカリ土類金属原子を表し、x、y、zはそれぞれ1≦x≦2、1≦y≦4、2≦z≦8を満たす整数である。)
Sc=ΔHh/(ΔHl+ΔHh)×100≧80 (2)
ここで、
ΔHh:示差走査熱量測定において昇温速度20℃/minで昇温した際のステレオコンプレックス結晶に基づく熱量(J/g)
ΔHl:示差走査熱量測定において昇温速度20℃/minで昇温した際のポリ−L−乳酸単独結晶およびポリ−D−乳酸単独結晶の結晶融解に基づく熱量(J/g)
(組合せ1)ポリ−L−乳酸またはポリ−D−乳酸のいずれか一方の重量平均分子量が60,000以上300,000以下であり、もう一方の重量平均分子量が10,000以上100,000以下である。
(組合せ2)ポリ−L−乳酸の重量平均分子量とポリ−D−乳酸の重量平均分子量との比が2以上30未満である。
Sc=ΔHh/(ΔHl+ΔHh)×100>60 (3)
ここで、
ΔHh:示差走査熱量測定において昇温速度20℃/minで昇温した際のステレオコンプレックス結晶の結晶融解に基づく熱量(J/g)
ΔHl:示差走査熱量測定において昇温速度20℃/minで昇温した際のポリ−L−乳酸単独結晶およびポリ−D−乳酸単独結晶の結晶融解に基づく熱量(J/g)
(組合せ3)ポリ−L−乳酸またはポリ−D−乳酸のいずれか一方の重量平均分子量が60,000以上300,000以下であり、もう一方の重量平均分子量が10,000以上50,000以下である。
(組合せ4)ポリ−L−乳酸の重量平均分子量とポリ−D−乳酸の重量平均分子量との比が2以上30未満である。
Sc=ΔHh/(ΔHl+ΔHh)×100>60 (3)
ここで、
ΔHh:示差走査熱量測定において昇温速度20℃/minで昇温した際のステレオコンプレックス結晶の結晶融解に基づく熱量(J/g)
ΔHl:示差走査熱量測定において昇温速度20℃/minで昇温した際のポリ−L−乳酸単独結晶およびポリ−D−乳酸単独結晶の結晶融解に基づく熱量(J/g)
1<(Tm−Tms)/(Tme−Tm)<1.8 (4)
Tm:示差走査熱量測定において昇温速度40℃/分で昇温した際の190℃以上250℃未満の温度の間で観測されるステレオコンプレックス結晶由来の融点
Tms:示差走査熱量測定において昇温速度40℃/分で昇温した際の190℃以上250℃未満の温度の間で観測されるステレオコンプレックス結晶の融解開始温度
Tme:示差走査熱量測定において昇温速度40℃/分で昇温した際の190℃以上250℃未満の温度の間で観測されるステレオコンプレックス結晶の融解終了温度
(組合せ5)ポリ−L−乳酸またはポリ−D−乳酸のいずれか一方の重量平均分子量が60,000以上300,000以下であり、もう一方の重量平均分子量が10,000以上100,000以下である。
(組合せ6)ポリ−L−乳酸の重量平均分子量とポリ−D−乳酸の重量平均分子量との比が2以上30未満である。
(組合せ7)ポリ−L−乳酸またはポリ−D−乳酸のいずれか一方の重量平均分子量が60,000以上300,000以下であり、もう一方の重量平均分子量が10,000以上50,000以下である。
(組合せ8)ポリ−L−乳酸の重量平均分子量とポリ−D−乳酸の重量平均分子量との比が2以上30未満である。
本発明で用いられるポリ乳酸系樹脂とは、ポリ−L−乳酸成分とポリ−D−乳酸成分とから構成されるポリ乳酸樹脂のことである。
本発明のポリ乳酸樹脂は、ポリ−L−乳酸成分とポリ−D−乳酸成分とからなることを特徴とする。ここで、ポリ乳酸樹脂はL−乳酸を主成分とするポリ−L−乳酸セグメントと、D−乳酸を主成分とするポリ−D−乳酸セグメントとから構成されるポリ乳酸ブロック共重合体を含有するか、あるいはポリ−L−乳酸成分およびポリ−D−乳酸成分からなり、ポリ−L−乳酸とポリ−D−乳酸とを混合することによって得られたポリ乳酸ステレオコンプレックスのどちらでも構わない。
Sc=ΔHh/(ΔHl+ΔHh)×100 (5)
平均連鎖長=I(a)/I(b) (6)
1<(Tm−Tms)/(Tme−Tm)<1.8 (4)
ここで、
Tm:示差走査型熱量計により測定され、ポリ乳酸ブロック共重合体を昇温速度40℃/分で30℃から250℃まで昇温した際の190℃以上250℃未満の温度の間で観測されるステレオコンプレックス結晶由来の融点
Tms:示差走査型熱量計により測定され、ポリ乳酸ブロック共重合体を昇温速度40℃/分で30℃から250℃まで昇温した際の190℃以上250℃未満の温度の間で観測されるステレオコンプレックス結晶の融解開始温度
Tme:示差走査型熱量計により測定され、ポリ乳酸ブロック共重合体を昇温速度40℃/分で30℃から250℃まで昇温した際の190℃以上250℃未満の温度の間で観測されるステレオコンプレックス結晶の融解終了温度
を示す。さらに好ましい範囲は1<(Tm−Tms)/(Tme−Tm)<1.6であり、1<(Tm−Tms)/(Tme−Tm)<1.4の範囲が特に好ましい。
ポリ乳酸ブロック共重合体の製造方法については、特に限定されるものではなく、一般のポリ乳酸製造方法を利用することができる。具体的には、原料の乳酸から生成した環状2量体のL−ラクチドまたはD−ラクチドのいずれか一方を触媒存在下で開環重合を行い、さらに該ポリ乳酸の光学異性体であるラクチドを添加して開環重合することでポリ乳酸ブロック共重合体を得るラクチド法(製法1)、当該原料を直接重合またはラクチドを経由した開環重合によりポリ−L−乳酸とポリ−D−乳酸とをそれぞれ重合し、次いで、得られたポリ−L−乳酸およびポリ−D−乳酸を混合後、固相重合によりポリ乳酸ブロック共重合体を得る方法(製法2)、ポリ−L−乳酸とポリ−D−乳酸とを、融点の高い方の成分の融解終了温度以上で長時間溶融混練を行うことで、L−乳酸単位のセグメントとD−乳酸単位のセグメントとをエステル交換反応させたポリ乳酸ブロック共重合体を得る方法(製法3)、多官能性化合物をポリ−L−乳酸およびポリ−D−乳酸に混合して反応することで、ポリ−L−乳酸とポリ−D−乳酸とを多官能性化合物で共有結合させポリ乳酸ブロック共重合体を得る方法(製法4)などがある。製法についてはいずれの方法を利用してもよいが、ポリ−L−乳酸およびポリ−D−乳酸を混合後、固相重合する方法が、ポリ乳酸ブロック共重合体一分子あたりに含まれるL−乳酸単位からなるセグメントおよびD−乳酸単位からなるセグメントの合計数が3以上となり、結果的に耐熱性、結晶性および機械物性を兼ね備えたポリ乳酸ブロック共重合体を得られるという点において好ましい。
開環重合にてポリ乳酸ブロック共重合体を得る方法としては、例えば、L−ラクチドまたはD−ラクチドのいずれか一方を触媒存在下で開環重合を行い、次いで他方の光学異性体であるラクチドを添加して開環重合を行うことでポリ乳酸ブロック共重合体を得る方法を挙げることができる。
次に、ポリ−L−乳酸とポリ−D−乳酸とを混合後、固相重合によりポリ乳酸ブロック共重合体を得る方法について説明する。本製法においてポリ−L−乳酸とポリ−D−乳酸の製造方法については、開環重合法および直接重合法のいずれの方法も用いることができる。
Sc=ΔHh/(ΔHl+ΔHh)×100>60 (3)
Y=Ws/Wp×100 (7)
次に、ポリ−L−乳酸およびポリ−D−乳酸を、融点の高い方の成分の融解終了温度以上で長時間溶融混練を行うことで、L−乳酸単位のセグメントとD−乳酸単位のセグメントとをエステル交換反応させたポリ乳酸ブロック共重合体を得る方法について説明する。本製法についても、ポリ−L−乳酸およびポリ−D−乳酸の製造方法については、上述した開環重合法および直接重合法のいずれの方法も用いることができる。
次に、多官能性化合物をポリ−L−乳酸およびポリ−D−乳酸に混合することで、ポリ−L−乳酸とポリ−D−乳酸とを多官能性化合物で共有結合させポリ乳酸ブロック共重合体を得る方法について説明する。本製法で用いるポリ−L−乳酸とポリ−D−乳酸の製造方法については、上述した開環重合法および直接重合法のいずれの方法も用いることができる。
本方法にてポリ乳酸ステレオコンプレックスを得るために用いるポリ−L−乳酸とポリ−D−乳酸との重量平均分子量は、ステレオコンプレックス形成率が高くなる点で、ポリ−L−乳酸およびポリ−D−乳酸のうちいずれか一方の重量平均分子量が30,000以上100,000以下であり、もう一方の重量平均分子量が10,000以上30,000以下であることが好ましい。さらに好ましくは、一方の重量平均分子量が35,000以上90,000以下、もう一方の重量平均分子量が10,000以上25,000以下である。特に好ましくは、一方の重量平均分子量が40,000以上80,000以下、もう一方の重量平均分子量が10,000以上20,000以下である。
Sc=ΔHh/(ΔHl+ΔHh)×100≧80 (2)
本発明のポリ乳酸樹脂組成物は、ポリ−L−乳酸成分とポリ−D−乳酸成分とからなるポリ乳酸樹脂100重量部に対して、リン酸金属塩を0.005重量部〜1重量部含むことを特徴とする。
MxHyPOz (1)
(一般式(1)において、Mはアルカリ金属原子またはアルカリ土類金属原子を表し、x、y、zはそれぞれ1≦x≦2、1≦y≦4、2≦z≦8を満たす整数である。)
重量平均分子量および分散度は、ゲルパーミエーションクロマトグラフィー(GPC)により測定した標準ポリメチルメタクリレート換算の値である。GPC測定は、検出器にWATERS社製の示差屈折計WATERS410を用い、ポンプにWATERS社製のMODEL510を用い、カラムに昭和電工株式会社製のShodex(登録商標) GPC HFIP−806Mと、Shodex(登録商標) GPC HFIP−LGとを直列に接続したものを用いて行った。測定条件は、流速0.5mL/minとし、測定では溶媒にヘキサフルオロイソプロパノールを用い、試料濃度1mg/mLの溶液を0.1mL注入した。
(2)熱的特性
融点、融解終了温度および融解熱量は、パーキンエルマー社製の示差走査型熱量計により測定した。測定条件は、試料5mg、窒素雰囲気下、昇温速度が20℃/分である。
ここで、融点とは、結晶融解ピークにおけるピークトップの温度のことを指し、また融解終了温度とは結晶融解ピークにおけるピーク終了温度のことを指す。得られた結果において、融点の上昇(高融点化)が見られたものは、ポリ乳酸ステレオコンプレックスが形成されたものと判断し、融点が変わらないものについてはポリ乳酸ステレオコンプレックスが形成されなかったものと判断した。ここで示す混合物の融点とは、第1昇温時に昇温速度20℃/分で30℃から250℃まで昇温したときに測定される融点であるのに対し、固相重合後のポリ乳酸ブロック共重合体の融点とは、第1昇温時に昇温速度20℃/分で30℃から250℃まで昇温した後、降温速度20℃/分で30℃まで冷却し、さらに第2昇温時に昇温速度20℃/分で30℃から250℃まで昇温したときに測定される融点のことである。
また、熱的特性として下記式(8)で示されるパラメータ値の算出を行った。
(Tm−Tms)/(Tme−Tm) (8)
式(8)のパラメータにおいて、
Tm:ポリ乳酸ブロック共重合体およびポリ乳酸ステレオコンプレックス(ポリ−L−乳酸とポリ−D−乳酸の混合物)の結晶由来の融点(結晶融解ピークにおけるピークトップ温度)
Tms:ポリ乳酸ブロック共重合体およびポリ乳酸ステレオコンプレックス(ポリ−L−乳酸とポリ−D−乳酸の混合物)の融解開始温度
Tme:ポリ乳酸ブロック共重合体およびポリ乳酸ステレオコンプレックス(ポリ−L−乳酸とポリ−D−乳酸の混合物)の融点終了温度
を示しており、それぞれの値はパーキンエルマー社製の示差走査型熱量計を用いて試料5mg、窒素雰囲気下での測定値である。なお、測定値は、第1昇温時に昇温速度40℃/分で30℃から250℃まで昇温した後、降温速度40℃/分で30℃まで冷却し、さらに第2昇温時に昇温速度40℃/分で30℃から250℃まで昇温したときの190℃以上250℃未満の温度の間で観測される値を用いている。
(3)ステレオコンプレックス形成率(Sc)
ポリ乳酸樹脂組成物のステレオコンプレックス形成率(Sc)は、下記式(5)から算出した。
Sc=ΔHh/(ΔHl+ΔHh)×100 (5)
ここで、ΔHlは150℃以上190℃未満に現れるポリ−L−乳酸単独結晶およびポリ−D−乳酸単独結晶の結晶融解に基づく熱量を示し、ΔHhは190℃以上250℃未満に現れるステレオコンプレックス結晶の結晶融解に基づく熱量を示す。
また、本実施例におけるポリ乳酸樹脂組成物のステレオコンプレックス形成率(Sc)は、示差走査型熱量計(DSC)の第2昇温時に測定される結晶融解ピークから算出したものである。
(4)降温結晶化温度
ポリ乳酸樹脂組成物の降温結晶化温度は、パーキンエルマー社製の示差走査型熱量計により測定した。具体的には、試料5mgを示差走査型熱量計において窒素雰囲気下で昇温速度20℃/minで30℃から250℃まで昇温した後、250℃で3分間恒温状態に維持を行い、冷却速度20℃/minで降温した際に測定される結晶化ピークトップの温度を降温結晶化温度とした。
(5)結晶化エンタルピー(ΔHc)
パーキンエルマー社製の示差走査型熱量計によって測定された結晶融解ピークのピーク面積を算出したものである。
(6)重量減少率
ポリ乳酸樹脂組成物の重量減少率は、パーキンエルマー社製の熱量計測定装置を用いた熱重量測定により測定した。具体的には、試料5mgを熱量計測定装置において窒素雰囲気下、240℃で30分間恒温状態にて加熱を行い、加熱前後の試料重量から重量減少率を算出した。
(7)ヘイズ値
成形体の透明性の指標としてヘイズ値の測定を行った。厚さ1mmのシート状成形体につき日本電色工業製ヘイズメーターNDH−300Aを用いて、JIS K 7105に従ってヘイズ値測定を行った。
(8)130℃貯蔵弾性率
成形体の耐熱性の指標として貯蔵弾性率を測定した。厚さ1mmのシート状成形体の中心部を40mm×2mmに切り出して短冊状のサンプルとし、動的粘弾性測定装置(セイコーインスツル株式会社製のDMS6100)にて窒素雰囲気下で昇温速度2℃/min、周波数3.5Hzにて動的粘弾性測定を行い、130℃における貯蔵弾性率を測定した。弾性率が高いほど耐熱性が高いといえる。
(9)引張強度
厚さ1mmのシート状成形体の中心部を40mm×2mmに切り出して短冊状のサンプルとし、ASTM D882に従い、引張強度を測定した。
(10)耐衝撃性
厚さ1mmのシート状成形体を真空成形して得られた容器に水を入れ、フタをした状態で2mの高さより容器底部からコンクリート上に落下させ、落下衝撃により容器が破損して水が漏れるまでの回数を測定し、下記の方法で評価を行った。
A:容器が破損して水が漏れるまでの落下回数が5回以上
B:容器が破損して水が漏れるまでの落下回数が2〜4回
F:容器が破損して水が漏れるまでの落下回数が1回
PLA1:参考例1で得られたポリ−L−乳酸(Mw=4.3万、分散度1.8)
PLA2:参考例2で得られたポリ−L−乳酸(Mw=13.5万、分散度1.8)
PLA3:参考例3で得られたポリ−L−乳酸(Mw=20.0万、分散度1.9)
PDA1:参考例4で得られたポリ−D−乳酸(Mw=3.5万、分散度1.5)
PDA2:参考例5で得られたポリ−D−乳酸(Mw=6.0万、分散度1.6)
PDA3:参考例6で得られたポリ−D−乳酸(Mw=7.5万、分散度1.6)
PDA4:参考例7で得られたポリ−D−乳酸(Mw=12.6万、分散度1.7)
PDA5:参考例8で得られたポリ−D−乳酸(Mw=19.8万、分散度1.8)
撹拌装置および還流装置を備えた反応容器中に、90%L−乳酸水溶液を50部入れ、温度を150℃にした後、徐々に減圧して水を留去しながら3.5時間反応した。その後、窒素雰囲気下で常圧にし、酢酸錫(II)0.02部を添加した後、170℃にて13Paになるまで徐々に減圧しながら7時間重合反応を行った。続いて、得られたポリ−L−乳酸を窒素雰囲気下で110℃、1時間結晶化処理を行った後、60Paの圧力下、140℃で3時間、150℃で3時間、160℃で5時間固相重合を行い、ポリ−L−乳酸(PLA1)を得た。PLA1の重量平均分子量は4.3万、分散度は1.8、融点は159℃であった。
160℃での固相重合時間を12時間に変更する以外は、参考例1と同様の方法にてポリ−L−乳酸の重合を行い、PLA2を得た。PLA2の重量平均分子量は13.5万、分散度は1.8、融点は168℃であった。
160℃での固相重合時間を18時間に変更する以外は、参考例1と同様の方法にてポリ−L−乳酸の重合を行い、PLA3を得た。PLA3の重量平均分子量は20.0万、分散度は1.9、融点は172℃であった。
撹拌装置と還流装置を備えた反応容器中に、90%D−乳酸水溶液を50部入れ、温度を150℃にした後、徐々に減圧して水を留去しながら3.5時間反応した。その後、窒素雰囲気下で常圧にし、酢酸錫(II)0.02部を添加した後、170℃にて13Paになるまで徐々に減圧しながら7時間重合反応を行った。続いて、得られたポリ−D−乳酸を窒素雰囲気下で110℃、1時間結晶化処理を行った後、60Paの圧力下、140℃で3時間、150℃で3時間、160℃で5時間固相重合を行い、ポリ−D−乳酸(PDA1)を得た。PDA1の重量平均分子量は3.5万、分散度は1.5、融点は155℃であった。
160℃での固相重合時間を7時間に変更する以外は、参考例4と同様の方法にてポリ−D−乳酸の重合を行い、PDA2を得た。PDA2の重量平均分子量は6.0万、分散度は1.6、融点は160℃であった。
160℃での固相重合時間を9時間に変更する以外は、参考例4と同様の方法にてポリ−D−乳酸の重合を行い、PDA3を得た。PDA3の重量平均分子量は7.5万、分散度は1.6、融点は162℃であった。
160℃での固相重合時間を12時間に変更する以外は、参考例4と同様の方法にてポリ−D−乳酸の重合を行い、PDA4を得た。PDA4の重量平均分子量は12.6万、分散度は1.7、融点は165℃であった。
160℃での固相重合時間を18時間に変更する以外は、参考例4と同様の方法にてポリ−D−乳酸の重合を行い、PDA5を得た。PDA5の重量平均分子量は19.8万、分散度は1.8、融点は170℃であった。
A−1:参考例9で得られたポリ乳酸ステレオコンプレックス(ポリ−L−乳酸とポリ−D−乳酸との混合物)(Mw=13万、分散度2.6)
A−2:参考例10で得られたポリ乳酸ブロック共重合体(Mw=16万、分散度2.3)
A−3:参考例11で得られたポリ乳酸ステレオコンプレックス(ポリ−L−乳酸とポリ−D−乳酸との混合物)(Mw=10万、分散度2.8)
A−4:参考例12で得られたポリ乳酸ブロック共重合体(Mw=13万、分散度2.4)
A−5:参考例13で得られたポリ乳酸ブロック共重合体(Mw=15万、分散度1.8)
A−6:参考例14で得られたポリ乳酸ステレオコンプレックス(ポリ−L−乳酸とポリ−D−乳酸との混合物)(Mw=3万、分散度1.8)
A−7:参考例15で得られたポリ乳酸ブロック共重合体(Mw=5万、分散度1.7)
A−8:参考例16で得られたポリ乳酸ステレオコンプレックス(ポリ−L−乳酸とポリ−D−乳酸との混合物)(Mw=9万、分散度2.4)
A−9:参考例17で得られたポリ乳酸ブロック共重合体(Mw=11万、分散度2.0)
A−10:参考例18で得られたポリ乳酸ステレオコンプレックス(ポリ−L−乳酸とポリ−D−乳酸との混合物)(Mw=11万、分散度1.9)
A−11:参考例19で得られたポリ乳酸ブロック共重合体(Mw=13万、分散度1.7)
A−12:参考例20で得られたポリ乳酸コンプレックス(ポリ−L−乳酸とポリ−D−乳酸との混合物)(Mw=15万、分散度1.8)
A−13:参考例21で得られたポリ乳酸ブロック共重合体(Mw=18万、分散度1.6)
A−14:参考例22で得られたポリ乳酸コンプレックス(ポリ−L−乳酸とポリ−D−乳酸との混合物)(Mw=16万、分散度1.8)
A−15:参考例23で得られたポリ乳酸ブロック共重合体(Mw=19万、分散度1.6)
A−16:参考例24で得られたポリ乳酸コンプレックス(ポリ−L−乳酸とポリ−D−乳酸との混合物)(Mw=18万、分散度1.8)
A−17:参考例25で得られたポリ乳酸ブロック共重合体(Mw=23万、分散度1.6)
PLA3:参考例3で得られたポリ−L−乳酸(Mw=20万、分散度1.9)
参考例3で得られたPLA3と参考例4で得られたPDA1を混合前にあらかじめ窒素雰囲気下で温度110℃、2時間結晶化処理を行った。続いて、結晶化した70重量部のPLA1を二軸押出機の樹脂供給口より添加し、30重量部のPDA1を後述するL/D=30の部分に設けたサイド供給口より添加することで溶融混練を行った。ここで、二軸押出機は、樹脂供給口よりL/D=10の部分に温度190℃に設定した可塑化部分を有するとともに、L/D=30の部分にニーディングディスクを備えてせん断付与できるスクリューとしてせん断付与下で混合できる構造を有している。二軸押出機によって、減圧下、混練温度210℃でPLA3およびPDA1の溶融混練を行い、ポリ乳酸ステレオコンプレックス(A−1)を得た。ポリ乳酸ステレオコンプレックス(A−1)の重量平均分子量は13万、分散度は2.6、融点は215℃と153℃とのダブルピークで、ステレオコンプレックス形成率は97%であった。
参考例9で得られたポリ乳酸ステレオコンプレックス(A−1)を、窒素雰囲気下で110℃、1時間結晶化処理を行った後、60Paの圧力下、140℃で3時間、150℃で3時間、160℃で18時間固相重合を行い、ポリ乳酸ブロック共重合体(A−2)を得た。ポリ乳酸ブロック共重合体(A−2)の重量平均分子量は16万、分散度は2.3、融点は211℃と171℃とのダブルピークで、ステレオコンプレックス形成率は98%であった。
二軸押出機に供給するPLA3を50重量部、PDA1を50重量部とする以外は参考例9と同様の方法で溶融混練を行い、ポリ乳酸ステレオコンプレックス(A−3)を得た。ポリ乳酸ステレオコンプレックス(A−3)の重量平均分子量は10万、分散度は2.8、融点は211℃で、ステレオコンプレックス形成率は100%であった。
参考例11で得られたポリ乳酸ステレオコンプレックス(A−3)を参考例10と同様の方法で固相重合を行い、ポリ乳酸ブロック共重合体(A−4)を得た。ポリ乳酸ブロック共重合体(A−4)の重量平均分子量は13万、分散度は2.4、融点は212℃で、ステレオコンプレックス形成率は100%であった。
L−ラクチド100部、エチレングリコール0.15部を撹拌装置のついた反応容器中で、窒素雰囲気下、160℃で均一に溶解させた後、オクチル酸錫0.01部を加え、2時間開環重合反応を行った。重合反応終了後、反応物をクロロホルムに溶解させ、メタノール(クロロホルム溶液の5倍量)中で撹拌しながら再沈殿させ、未反応のモノマーを除去してポリ−L−乳酸(PLA4)を得た。PLA4の重量平均分子量は8万、分散度は1.6、融点は168℃であった。
二軸押出機に供給するPLA3をPLA1にする以外は参考例9と同様の方法で溶融混練を行い、ポリ乳酸ステレオコンプレックス(A−6)を得た。A−6の重量平均分子量は3万、分散度は1.8、融点は215℃で、ステレオコンプレックス形成率は100%であった。
参考例14で得られたポリ乳酸ステレオコンプレックス(A−6)を参考例10と同様の方法で固相重合を行い、ポリ乳酸ブロック共重合体(A−7)を得た。A−7の重量平均分子量は5万、分散度は1.7、融点は213℃で、ステレオコンプレックス形成率は100%であった。
二軸押出機に供給するPLA3をPLA2にする以外は参考例9と同様の方法で溶融混練を行い、ポリ乳酸ステレオコンプレックス(A−8)を得た。A−8の重量平均分子量は9万、分散度は2.4、融点は214℃で、ステレオコンプレックス形成率は100%であった。
参考例14で得られたポリ乳酸ステレオコンプレックス(A−8)を参考例10と同様の方法で固相重合を行い、ポリ乳酸ブロック共重合体(A−9)を得た。A−9の重量平均分子量は11万、分散度は2.0、融点は212℃で、ステレオコンプレックス形成率は100%であった。
二軸押出機に供給するPLA3をPLA2に、PDA1をPDA4に変更する以外は参考例9と同様の方法で溶融混練を行い、ポリ乳酸ステレオコンプレックス(A−10)を得た。A−10の重量平均分子量は11万、分散度は1.9、融点は213℃と165℃のダブルピークで、ステレオコンプレックス形成率は68%であった。
参考例18で得られたポリ乳酸ステレオコンプレックス(A−10)を参考例10と同様の方法で固相重合を行い、ポリ乳酸ブロック共重合体(A−11)を得た。A−11の重量平均分子量は13万、分散度は1.7、融点は210℃と168℃のダブルピークで、ステレオコンプレックス形成率は73%であった。
二軸押出機に供給するPDA1をPDA2に変更する以外は参考例9と同様の方法で溶融混練を行い、ポリ乳酸ステレオコンプレックス(A−12)を得た。A−12の重量平均分子量は15万、分散度は1.8、融点は210℃と158℃のダブルピークで、ステレオコンプレックス形成率は90%であった。
参考例20で得られたポリ乳酸ステレオコンプレックス(A−12)を参考例10と同様の方法で固相重合を行い、ポリ乳酸ブロック共重合体(A−13)を得た。A−13の重量平均分子量は18万、分散度は1.6、融点は209℃と170℃のダブルピークで、ステレオコンプレックス形成率は95%であった。
二軸押出機に供給するPDA1をPDA3に変更する以外は参考例9と同様の方法で溶融混練を行い、ポリ乳酸ステレオコンプレックス(A−14)を得た。A−14の重量平均分子量は16万、分散度は1.8、融点は212℃と160℃のダブルピークで、ステレオコンプレックス形成率は82%であった。
参考例22で得られたポリ乳酸ステレオコンプレックス(A−14)を参考例10と同様の方法で固相重合を行い、ポリ乳酸ブロック共重合体(A−15)を得た。A−15の重量平均分子量は19万、分散度は1.6、融点は210℃と172℃のダブルピークで、ステレオコンプレックス形成率は88%であった。
二軸押出機に供給するPDA1をPDA5に変更する以外は参考例9と同様の方法で溶融混練を行い、ポリ乳酸ステレオコンプレックス(A−16)を得た。A−16の重量平均分子量は18万、分散度は1.8、融点は212℃と171℃のダブルピークで、ステレオコンプレックス形成率は50%であった。
参考例20で得られたポリ乳酸ステレオコンプレックス(A−16)を参考例10と同様の方法で固相重合を行い、ポリ乳酸ブロック共重合体(A−17)を得た。A−17の重量平均分子量は23万、分散度は1.6、融点は209℃と175℃のダブルピークで、ステレオコンプレックス形成率は61%であった。
B−1:リン酸二水素ナトリウム(和光純薬工業株式会社製)
B−2:リン酸二水素カリウム(和光純薬工業株式会社製)
B−3:リン酸二水素カルシウム(和光純薬工業株式会社製)
B−4:リン酸水素二ナトリウム(和光純薬工業株式会社製)
B−5:リン酸水素二カリウム(和光純薬工業株式会社製)
B−6:ジオフタデミルホスフェート(株式会社ADEKA製「アデカスタブ(登録商標)」AX−71)
B−7:リン酸エステルアルミニウム塩(株式会社ADEKA製「アデカスタブ(登録商標)」NA−21)
C−1:エポキシ基含有スチレン/アクリル酸エステル共重合体(BASF社製「JONCRYL(登録商標) ADR−4368」、Mw(PMMA換算)8,000、エポキシ当量285g/mol)
表1〜表3に示す種々の割合で、ポリ乳酸樹脂(A)、リン系化合物(B)および多官能性化合物(C)をあらかじめドライブレンドした後、ベントを有する二軸押出機にて溶融混練を行った。二軸押出機は、上述したように、樹脂供給口よりL/D=10の部分に温度225℃に設定した可塑化部分と、L/D=30の部分にニーディングディスクを備えてせん断付与できるスクリューとしてせん断付与下で混合できる構造とを有しており、この二軸押出機を用いて減圧下、混練温度220℃で溶融混練を行って、ペレット化されたポリ乳酸樹脂組成物を得た。溶融混練により得られたポリ乳酸樹脂組成物の物性は表1〜表3に示す通りである。
実施例1〜26と同様に、表4に示す種々の割合で、ポリ乳酸樹脂(A)、リン系化合物(B)および多官能性化合物(C)をあらかじめドライブレンドした後、ベントを有する二軸押出機にて溶融混練を行った。比較例1〜7においても、上述した二軸押出機を用いてペレット化されたポリ乳酸樹脂組成物を得た。溶融混練により得られたポリ乳酸樹脂組成物の物性は表4に示す通りである。
Claims (16)
- ポリ−L−乳酸成分とポリ−D−乳酸成分とからなるポリ乳酸樹脂100重量部に対して下記一般式(1)で示すリン酸金属塩を0.005重量部〜1.2重量部含むポリ乳酸樹脂組成物であって、示差走査熱量測定において、当該ポリ乳酸樹脂組成物を250℃まで昇温して3分間恒温状態にした後、冷却速度20℃/minで降温した際の結晶化熱量が5J/g以上であるポリ乳酸樹脂組成物。
MxHyPOz (1)
(一般式(1)において、Mはアルカリ金属原子またはアルカリ土類金属原子を表し、x、y、zはそれぞれ1≦x≦2、1≦y≦4、2≦z≦8を満たす整数である。) - 前記ポリ乳酸樹脂は、
L−乳酸を主成分とするポリ−L−乳酸セグメントと、
D−乳酸を主成分とするポリ−D−乳酸セグメントと、
から構成されるポリ乳酸ブロック共重合体を含有する請求項1に記載のポリ乳酸樹脂組成物。 - 前記ポリ乳酸樹脂は、ポリ−L−乳酸およびポリ−D−乳酸を混合して得られたものであり、ステレオコンプレックス形成率(Sc)が、下記式(2)を満たすポリ乳酸ステレオコンプレックスである請求項1に記載のポリ乳酸樹脂組成物。
Sc=ΔHh/(ΔHl+ΔHh)×100≧80 (2)
ここで、
ΔHh:示差走査熱量測定において昇温速度20℃/minで昇温した際のステレオコンプレックス結晶の結晶融解に基づく熱量(J/g)
ΔHl:示差走査熱量測定において昇温速度20℃/minで昇温した際のポリ−L−乳酸単独結晶およびポリ−D−乳酸単独結晶の結晶融解に基づく熱量(J/g) - 前記リン酸金属塩は、リン酸二水素ナトリウム、リン酸二水素カリウム、リン酸二水素リチウム、リン酸二水素カルシウム、リン酸水素二ナトリウム、リン酸水素二カリウム、リン酸水素カルシウム、リン酸水素バリウム、リン酸水素マグネシウム、亜リン酸水素ナトリウム、亜リン酸カリウム、亜リン酸水素カルシウム、次亜リン酸ナトリウム、次亜リン酸カリウム、次亜リン酸カルシウムから選ばれる少なくとも一種である請求項1〜3のいずれかに記載のポリ乳酸樹脂組成物。
- 前記ポリ乳酸樹脂は、該ポリ乳酸樹脂100重量部に対して多官能性化合物を0.01重量部〜20重量部添加して得られる請求項1〜4のいずれかに記載のポリ乳酸樹脂組成物。
- 前記多官能性化合物が、多価カルボン酸無水物、多価イソシアネート、多価アルコール、多価エポキシ化合物から選ばれる少なくとも一種である請求項5に記載のポリ乳酸樹脂組成物。
- 熱重量測定において、当該ポリ乳酸樹脂組成物を240℃、30分間加熱した後の重量減少率が1.0%未満である請求項1〜6のいずれかに記載のポリ乳酸樹脂組成物。
- 前記ポリ乳酸ブロック共重合体は、ポリ−L−乳酸およびポリ−D−乳酸を下記組合せ1および/または下記組合せ2の条件で混合し、重量平均分子量90,000以上、かつステレオコンプレックス形成率(Sc)が下記式(3)を満たす混合物を得た後、該混合物の融点より低い温度で固相重合することにより得られる請求項2に記載のポリ乳酸樹脂組成物。
(組合せ1)ポリ−L−乳酸またはポリ−D−乳酸のいずれか一方の重量平均分子量が60,000以上300,000以下であり、もう一方の重量平均分子量が10,000以上100,000以下である。
(組合せ2)ポリ−L−乳酸の重量平均分子量とポリ−D−乳酸の重量平均分子量との比が2以上30未満である。
Sc=ΔHh/(ΔHl+ΔHh)×100>60 (3)
ここで、
ΔHh:示差走査熱量測定において昇温速度20℃/minで昇温した際のステレオコンプレックス結晶に基づく熱量(J/g)
ΔHl:示差走査熱量測定において昇温速度20℃/minで昇温した際のポリ−L−乳酸単独結晶およびポリ−D−乳酸単独結晶の結晶融解に基づく熱量(J/g) - 前記ポリ乳酸ブロック共重合体は、ポリ−L−乳酸およびポリ−D−乳酸を下記組合せ3および/または下記組合せ4の条件で混合し、重量平均分子量90,000以上、かつステレオコンプレックス形成率(Sc)が下記式(3)を満たす混合物を得た後、該混合物の融点より低い温度で固相重合することにより得られる請求項2に記載のポリ乳酸樹脂組成物。
(組合せ3)ポリ−L−乳酸またはポリ−D−乳酸のいずれか一方の重量平均分子量が60,000以上300,000以下であり、もう一方の重量平均分子量が10,000以上50,000以下である。
(組合せ4)ポリ−L−乳酸の重量平均分子量とポリ−D−乳酸の重量平均分子量との比が2以上30未満である。
Sc=ΔHh/(ΔHl+ΔHh)×100>60 (3)
ここで、
ΔHh:示差走査熱量測定において昇温速度20℃/minで昇温した際のステレオコンプレックス結晶に基づく熱量(J/g)
ΔHl:示差走査熱量測定において昇温速度20℃/minで昇温した際のポリ−L−乳酸単独結晶およびポリ−D−乳酸単独結晶の結晶融解に基づく熱量(J/g) - 前記ポリ乳酸ブロック共重合体は、下記式(4)を満たす請求項2または8および9に記載のポリ乳酸樹脂組成物。
1<(Tm−Tms)/(Tme−Tm)<1.8 (4)
Tm:示差走査熱量測定において昇温速度40℃/分で昇温した際の190℃以上250℃未満の温度の間で観測されるステレオコンプレックス結晶由来の融点
Tms:示差走査熱量測定において昇温速度40℃/分で昇温した際の190℃以上250℃未満の温度の間で観測されるステレオコンプレックス結晶の融解開始温度
Tme:示差走査熱量測定において昇温速度40℃/分で昇温した際の190℃以上250℃未満の温度の間で観測されるステレオコンプレックス結晶の融解終了温度 - 前記ポリ乳酸ステレオコンプレックスは、ポリ−L−乳酸およびポリ−D−乳酸を下記組合せ5および/または下記組合せ6の条件で混合し、該混合物の重量平均分子量が90,000以上である請求項3〜7のいずれかに記載のポリ乳酸樹脂組成物。
(組合せ5)ポリ−L−乳酸またはポリ−D−乳酸のいずれか一方の重量平均分子量が60,000以上300,000以下であり、もう一方の重量平均分子量が10,000以上100,000以下である。
(組合せ6)ポリ−L−乳酸の重量平均分子量とポリ−D−乳酸の重量平均分子量との比が2以上30未満である。 - 前記ポリ乳酸ステレオコンプレックスは、ポリ−L−乳酸およびポリ−D−乳酸を下記組合せ7および/または下記組合せ8の条件で混合し、該混合物の重量平均分子量が90,000以上である請求項3〜7のいずれかに記載のポリ乳酸樹脂組成物。
(組合せ7)ポリ−L−乳酸またはポリ−D−乳酸のいずれか一方の重量平均分子量が60,000以上300,000以下であり、もう一方の重量平均分子量が10,000以上50,000以下である。
(組合せ8)ポリ−L−乳酸の重量平均分子量とポリ−D−乳酸の重量平均分子量との比が2以上30未満である。 - 前記ポリ乳酸樹脂の重量平均分子量が100,000以上300,000以下である請求項1〜12のいずれかに記載のポリ乳酸樹脂組成物。
- 請求項1〜13のいずれかに記載のポリ乳酸樹脂組成物からなる成形体。
- 請求項2に記載のポリ乳酸樹脂組成物の製造方法であって、
前記ポリ乳酸ブロック共重合体を得た後、前記リン酸金属塩を溶融混練するポリ乳酸樹脂組成物の製造方法。 - 請求項3記載のポリ乳酸樹脂組成物の製造方法であって、
前記ポリ乳酸ステレオコンプレックスを得た後、前記リン酸金属塩を溶融混練するポリ乳酸樹脂組成物の製造方法。
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JP6771380B2 (ja) | 2014-07-04 | 2020-10-21 | 帝人株式会社 | ポリ乳酸組成物、ポリ乳酸組成物から得られる成形体、およびポリ乳酸組成物の製造方法 |
CN105315416B (zh) * | 2015-12-02 | 2018-02-23 | 河北麦格尼菲复合材料股份有限公司 | 可再生生物基乙烯基酯树脂及其制备方法 |
TWI609028B (zh) | 2016-05-06 | 2017-12-21 | 財團法人工業技術研究院 | 共聚物與含其之樹脂組合物、封裝膜及封裝結構 |
BR112018074284B1 (pt) * | 2016-06-07 | 2022-08-16 | Basf Se | Processo para a preparação de grânulos expansíveis contendo ácido polilático |
KR101865813B1 (ko) * | 2016-12-23 | 2018-06-11 | 한국과학기술연구원 | 폴리락트산 복합체 제조방법 |
EP3428314B1 (de) | 2017-07-14 | 2019-11-13 | Ewald Dörken Ag | Zusammensetzung und verfahren zur passivierung verzinkter bauteile |
US10450201B2 (en) * | 2017-10-04 | 2019-10-22 | King Fahd University Of Petroleum And Minerals | Method for the synthesis of nanoparticles of heterometallic nanocomposite materials |
US11643261B2 (en) * | 2020-02-28 | 2023-05-09 | Illinois Tool Works Inc. | Biodegradable multi-pack carriers |
CN111349326A (zh) * | 2020-04-30 | 2020-06-30 | 安徽宏飞钓具有限公司 | 一种柔软环保型仿生鱼饵及其制备方法 |
CN111548504B (zh) * | 2020-05-27 | 2021-10-22 | 四川大学 | 具有优异熔融稳定性与熔融加工性能的立构复合聚乳酸材料或制品及其制备方法 |
CN112791710B (zh) * | 2020-12-24 | 2022-04-01 | 天津工业大学 | 一种改性聚合物纤维球及其制备方法和Cd(Ⅱ)污染土壤的修复方法 |
CN113831701A (zh) * | 2021-11-16 | 2021-12-24 | 上海昶法新材料有限公司 | 改性生物基诱虫带及其制备方法 |
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US20150259504A1 (en) | 2015-09-17 |
KR20150070117A (ko) | 2015-06-24 |
EP2907849A1 (en) | 2015-08-19 |
CN104704050A (zh) | 2015-06-10 |
US9920181B2 (en) | 2018-03-20 |
JP6191460B2 (ja) | 2017-09-06 |
TW201425460A (zh) | 2014-07-01 |
WO2014057766A1 (ja) | 2014-04-17 |
EP2907849A4 (en) | 2016-06-08 |
CN104704050B (zh) | 2016-10-12 |
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