JP5630439B2 - ポリ乳酸ブロック共重合体の製造方法 - Google Patents
ポリ乳酸ブロック共重合体の製造方法 Download PDFInfo
- Publication number
- JP5630439B2 JP5630439B2 JP2011535342A JP2011535342A JP5630439B2 JP 5630439 B2 JP5630439 B2 JP 5630439B2 JP 2011535342 A JP2011535342 A JP 2011535342A JP 2011535342 A JP2011535342 A JP 2011535342A JP 5630439 B2 JP5630439 B2 JP 5630439B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- lactic acid
- poly
- polylactic acid
- block copolymer
- 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.)
- Expired - Fee Related
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- 229920000747 poly(lactic acid) Polymers 0.000 title claims description 231
- 239000004626 polylactic acid Substances 0.000 title claims description 231
- 229920001400 block copolymer Polymers 0.000 title claims description 135
- 238000000034 method Methods 0.000 title claims description 64
- 230000008569 process Effects 0.000 title claims description 9
- 229920001432 poly(L-lactide) Polymers 0.000 claims description 146
- 238000002844 melting Methods 0.000 claims description 141
- 230000008018 melting Effects 0.000 claims description 139
- JVTAAEKCZFNVCJ-UWTATZPHSA-N D-lactic acid Chemical compound C[C@@H](O)C(O)=O JVTAAEKCZFNVCJ-UWTATZPHSA-N 0.000 claims description 129
- 229940022769 d- lactic acid Drugs 0.000 claims description 115
- 238000006116 polymerization reaction Methods 0.000 claims description 107
- 239000000203 mixture Substances 0.000 claims description 87
- -1 rare earth compound Chemical class 0.000 claims description 79
- 239000007790 solid phase Substances 0.000 claims description 75
- 239000013078 crystal Substances 0.000 claims description 64
- 238000004519 manufacturing process Methods 0.000 claims description 63
- 238000002156 mixing Methods 0.000 claims description 62
- 239000003054 catalyst Substances 0.000 claims description 58
- JVTAAEKCZFNVCJ-REOHCLBHSA-N L-lactic acid Chemical group C[C@H](O)C(O)=O JVTAAEKCZFNVCJ-REOHCLBHSA-N 0.000 claims description 53
- 238000002425 crystallisation Methods 0.000 claims description 47
- 230000008025 crystallization Effects 0.000 claims description 46
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 34
- 230000015572 biosynthetic process Effects 0.000 claims description 30
- 239000006185 dispersion Substances 0.000 claims description 19
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 18
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 16
- 238000005259 measurement Methods 0.000 claims description 13
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 claims description 13
- 238000001816 cooling Methods 0.000 claims description 12
- 239000002994 raw material Substances 0.000 claims description 12
- 150000003606 tin compounds Chemical class 0.000 claims description 12
- 229930182843 D-Lactic acid Natural products 0.000 claims description 10
- PNOXNTGLSKTMQO-UHFFFAOYSA-L diacetyloxytin Chemical compound CC(=O)O[Sn]OC(C)=O PNOXNTGLSKTMQO-UHFFFAOYSA-L 0.000 claims description 10
- 239000004310 lactic acid Substances 0.000 claims description 10
- 150000003609 titanium compounds Chemical class 0.000 claims description 10
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 9
- IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical compound [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 claims description 9
- 235000014655 lactic acid Nutrition 0.000 claims description 8
- 229910052761 rare earth metal Inorganic materials 0.000 claims description 8
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 claims description 7
- 229910021626 Tin(II) chloride Inorganic materials 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 6
- 150000002506 iron compounds Chemical class 0.000 claims description 6
- 150000002642 lithium compounds Chemical class 0.000 claims description 6
- 235000011150 stannous chloride Nutrition 0.000 claims description 6
- 229960003080 taurine Drugs 0.000 claims description 6
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 claims description 6
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims description 6
- 150000003752 zinc compounds Chemical class 0.000 claims description 6
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 claims description 5
- CAXRKYFRLOPCAB-UHFFFAOYSA-N propane-1,1-disulfonic acid Chemical compound CCC(S(O)(=O)=O)S(O)(=O)=O CAXRKYFRLOPCAB-UHFFFAOYSA-N 0.000 claims description 5
- 150000001869 cobalt compounds Chemical class 0.000 claims description 4
- 229920001577 copolymer Polymers 0.000 claims description 4
- 150000002611 lead compounds Chemical class 0.000 claims description 4
- YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 claims description 4
- GINSRDSEEGBTJO-UHFFFAOYSA-N thietane 1-oxide Chemical compound O=S1CCC1 GINSRDSEEGBTJO-UHFFFAOYSA-N 0.000 claims 1
- 230000000052 comparative effect Effects 0.000 description 71
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 28
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 27
- 239000000047 product Substances 0.000 description 27
- 238000004898 kneading Methods 0.000 description 26
- 239000012299 nitrogen atmosphere Substances 0.000 description 25
- 229920000642 polymer Polymers 0.000 description 20
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 18
- 229910052757 nitrogen Inorganic materials 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 230000000704 physical effect Effects 0.000 description 17
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 16
- 238000010438 heat treatment Methods 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 229910052751 metal Inorganic materials 0.000 description 15
- 239000010408 film Substances 0.000 description 14
- RBMHUYBJIYNRLY-UHFFFAOYSA-N 2-[(1-carboxy-1-hydroxyethyl)-hydroxyphosphoryl]-2-hydroxypropanoic acid Chemical compound OC(=O)C(O)(C)P(O)(=O)C(C)(O)C(O)=O RBMHUYBJIYNRLY-UHFFFAOYSA-N 0.000 description 13
- 238000005227 gel permeation chromatography Methods 0.000 description 13
- 239000002184 metal Substances 0.000 description 13
- 238000000465 moulding Methods 0.000 description 13
- 229920001434 poly(D-lactide) Polymers 0.000 description 13
- 239000000377 silicon dioxide Substances 0.000 description 12
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 11
- 239000003377 acid catalyst Substances 0.000 description 11
- 230000000630 rising effect Effects 0.000 description 11
- 229910019142 PO4 Inorganic materials 0.000 description 10
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 10
- 239000010452 phosphate Substances 0.000 description 10
- 229920005989 resin Polymers 0.000 description 10
- 239000011347 resin Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 10
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 9
- 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 9
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 8
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 8
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 8
- 239000002685 polymerization catalyst Substances 0.000 description 8
- 238000003860 storage Methods 0.000 description 8
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 150000005846 sugar alcohols Polymers 0.000 description 7
- XZOYHFBNQHPJRQ-UHFFFAOYSA-N 7-methyloctanoic acid Chemical compound CC(C)CCCCCC(O)=O XZOYHFBNQHPJRQ-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 6
- GUNJVIDCYZYFGV-UHFFFAOYSA-K antimony trifluoride Chemical compound F[Sb](F)F GUNJVIDCYZYFGV-UHFFFAOYSA-K 0.000 description 6
- 229910052797 bismuth Inorganic materials 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 230000009918 complex formation Effects 0.000 description 6
- 239000003484 crystal nucleating agent Substances 0.000 description 6
- 230000009849 deactivation Effects 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000000835 fiber Substances 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 230000009477 glass transition Effects 0.000 description 6
- 229940049918 linoleate Drugs 0.000 description 6
- 229910052744 lithium Inorganic materials 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- 230000003647 oxidation Effects 0.000 description 6
- 238000007254 oxidation reaction Methods 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 6
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 239000011342 resin composition Substances 0.000 description 6
- 235000010215 titanium dioxide Nutrition 0.000 description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 description 5
- 229920000178 Acrylic resin Polymers 0.000 description 5
- 239000004925 Acrylic resin Substances 0.000 description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 5
- 238000000071 blow moulding Methods 0.000 description 5
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- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 5
- 238000004806 packaging method and process Methods 0.000 description 5
- 229920003023 plastic Polymers 0.000 description 5
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- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 5
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- 150000003460 sulfonic acids Chemical class 0.000 description 5
- JJTUDXZGHPGLLC-IMJSIDKUSA-N 4511-42-6 Chemical compound C[C@@H]1OC(=O)[C@H](C)OC1=O JJTUDXZGHPGLLC-IMJSIDKUSA-N 0.000 description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
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- 239000004593 Epoxy Substances 0.000 description 4
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 150000001463 antimony compounds Chemical class 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- JALQQBGHJJURDQ-UHFFFAOYSA-L bis(methylsulfonyloxy)tin Chemical compound [Sn+2].CS([O-])(=O)=O.CS([O-])(=O)=O JALQQBGHJJURDQ-UHFFFAOYSA-L 0.000 description 4
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 4
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 4
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 4
- 150000007942 carboxylates Chemical class 0.000 description 4
- 239000004927 clay Substances 0.000 description 4
- 229910017052 cobalt Inorganic materials 0.000 description 4
- 239000010941 cobalt Substances 0.000 description 4
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 4
- XLJKHNWPARRRJB-UHFFFAOYSA-N cobalt(2+) Chemical compound [Co+2] XLJKHNWPARRRJB-UHFFFAOYSA-N 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- FRXGWNKDEMTFPL-UHFFFAOYSA-N dioctadecyl hydrogen phosphate Chemical compound CCCCCCCCCCCCCCCCCCOP(O)(=O)OCCCCCCCCCCCCCCCCCC FRXGWNKDEMTFPL-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 150000002366 halogen compounds Chemical class 0.000 description 4
- 229920001519 homopolymer Polymers 0.000 description 4
- 239000011261 inert gas Substances 0.000 description 4
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- 239000012948 isocyanate Substances 0.000 description 4
- 150000002513 isocyanates Chemical class 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 description 4
- MRELNEQAGSRDBK-UHFFFAOYSA-N lanthanum(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[La+3].[La+3] MRELNEQAGSRDBK-UHFFFAOYSA-N 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 4
- 239000001095 magnesium carbonate Substances 0.000 description 4
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 4
- 235000014380 magnesium carbonate Nutrition 0.000 description 4
- 239000000395 magnesium oxide Substances 0.000 description 4
- 235000012245 magnesium oxide Nutrition 0.000 description 4
- 229940091250 magnesium supplement Drugs 0.000 description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- XTEGVFVZDVNBPF-UHFFFAOYSA-N naphthalene-1,5-disulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 0.000 description 4
- PLDDOISOJJCEMH-UHFFFAOYSA-N neodymium(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Nd+3].[Nd+3] PLDDOISOJJCEMH-UHFFFAOYSA-N 0.000 description 4
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 4
- UHGIMQLJWRAPLT-UHFFFAOYSA-N octadecyl dihydrogen phosphate Chemical compound CCCCCCCCCCCCCCCCCCOP(O)(O)=O UHGIMQLJWRAPLT-UHFFFAOYSA-N 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 239000008188 pellet Substances 0.000 description 4
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 239000011574 phosphorus Substances 0.000 description 4
- 239000004014 plasticizer Substances 0.000 description 4
- 230000037048 polymerization activity Effects 0.000 description 4
- KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 4
- QCZFMLDHLOYOQJ-UHFFFAOYSA-H samarium(3+);tricarbonate Chemical compound [Sm+3].[Sm+3].[O-]C([O-])=O.[O-]C([O-])=O.[O-]C([O-])=O QCZFMLDHLOYOQJ-UHFFFAOYSA-H 0.000 description 4
- FKTOIHSPIPYAPE-UHFFFAOYSA-N samarium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[Sm+3].[Sm+3] FKTOIHSPIPYAPE-UHFFFAOYSA-N 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- 238000004904 shortening Methods 0.000 description 4
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- KCIDZIIHRGYJAE-YGFYJFDDSA-L dipotassium;[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate Chemical compound [K+].[K+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@H]1O KCIDZIIHRGYJAE-YGFYJFDDSA-L 0.000 description 2
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- TVQLLNFANZSCGY-UHFFFAOYSA-N disodium;dioxido(oxo)tin Chemical compound [Na+].[Na+].[O-][Sn]([O-])=O TVQLLNFANZSCGY-UHFFFAOYSA-N 0.000 description 2
- PWWSSIYVTQUJQQ-UHFFFAOYSA-N distearyl thiodipropionate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCCCCCC PWWSSIYVTQUJQQ-UHFFFAOYSA-N 0.000 description 2
- YDKNIVGNQVFYPR-UHFFFAOYSA-L dodecanoate;lead(2+) Chemical compound [Pb+2].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O YDKNIVGNQVFYPR-UHFFFAOYSA-L 0.000 description 2
- PYBNTRWJKQJDRE-UHFFFAOYSA-L dodecanoate;tin(2+) Chemical compound [Sn+2].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O PYBNTRWJKQJDRE-UHFFFAOYSA-L 0.000 description 2
- TVACALAUIQMRDF-UHFFFAOYSA-N dodecyl dihydrogen phosphate Chemical compound CCCCCCCCCCCCOP(O)(O)=O TVACALAUIQMRDF-UHFFFAOYSA-N 0.000 description 2
- HKCSKROOVZMKSO-UHFFFAOYSA-K dysprosium(3+);triacetate Chemical compound [Dy+3].CC([O-])=O.CC([O-])=O.CC([O-])=O HKCSKROOVZMKSO-UHFFFAOYSA-K 0.000 description 2
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- 239000000806 elastomer Substances 0.000 description 2
- AFAXGSQYZLGZPG-UHFFFAOYSA-N ethanedisulfonic acid Chemical compound OS(=O)(=O)CCS(O)(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-N 0.000 description 2
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- FANAUDUYRDVPHX-UHFFFAOYSA-N ethoxytin Chemical compound CCO[Sn] FANAUDUYRDVPHX-UHFFFAOYSA-N 0.000 description 2
- CJMZLCRLBNZJQR-UHFFFAOYSA-N ethyl 2-amino-4-(4-fluorophenyl)thiophene-3-carboxylate Chemical compound CCOC(=O)C1=C(N)SC=C1C1=CC=C(F)C=C1 CJMZLCRLBNZJQR-UHFFFAOYSA-N 0.000 description 2
- SULCVUWEGVSCPF-UHFFFAOYSA-L europium(2+);carbonate Chemical compound [Eu+2].[O-]C([O-])=O SULCVUWEGVSCPF-UHFFFAOYSA-L 0.000 description 2
- DHBSQUMIAQRVAW-UHFFFAOYSA-N europium(3+);propan-2-olate Chemical compound [Eu+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] DHBSQUMIAQRVAW-UHFFFAOYSA-N 0.000 description 2
- LNYNHRRKSYMFHF-UHFFFAOYSA-K europium(3+);triacetate Chemical compound [Eu+3].CC([O-])=O.CC([O-])=O.CC([O-])=O LNYNHRRKSYMFHF-UHFFFAOYSA-K 0.000 description 2
- NNMXSTWQJRPBJZ-UHFFFAOYSA-K europium(iii) chloride Chemical compound Cl[Eu](Cl)Cl NNMXSTWQJRPBJZ-UHFFFAOYSA-K 0.000 description 2
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- NJVOZLGKTAPUTQ-UHFFFAOYSA-M fentin chloride Chemical compound C=1C=CC=CC=1[Sn](C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 NJVOZLGKTAPUTQ-UHFFFAOYSA-M 0.000 description 2
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- 239000003337 fertilizer Substances 0.000 description 2
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- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 2
- 150000002291 germanium compounds Chemical class 0.000 description 2
- YBMRDBCBODYGJE-UHFFFAOYSA-N germanium oxide Inorganic materials O=[Ge]=O YBMRDBCBODYGJE-UHFFFAOYSA-N 0.000 description 2
- OLQSNYOQJMTVNH-UHFFFAOYSA-N germanium(4+);oxygen(2-) Chemical compound [O-2].[O-2].[Ge+4] OLQSNYOQJMTVNH-UHFFFAOYSA-N 0.000 description 2
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- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 2
- 230000001771 impaired effect Effects 0.000 description 2
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- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 2
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- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 2
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- VQEHIYWBGOJJDM-UHFFFAOYSA-H lanthanum(3+);trisulfate Chemical compound [La+3].[La+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O VQEHIYWBGOJJDM-UHFFFAOYSA-H 0.000 description 2
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- 239000007788 liquid Substances 0.000 description 2
- FUJCRWPEOMXPAD-UHFFFAOYSA-N lithium oxide Chemical compound [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 2
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- INHCSSUBVCNVSK-UHFFFAOYSA-L lithium sulfate Chemical compound [Li+].[Li+].[O-]S([O-])(=O)=O INHCSSUBVCNVSK-UHFFFAOYSA-L 0.000 description 2
- MXIRPJHGXWFUAE-UHFFFAOYSA-N lithium;propan-1-olate Chemical compound [Li+].CCC[O-] MXIRPJHGXWFUAE-UHFFFAOYSA-N 0.000 description 2
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- OVGXLJDWSLQDRT-UHFFFAOYSA-L magnesium lactate Chemical compound [Mg+2].CC(O)C([O-])=O.CC(O)C([O-])=O OVGXLJDWSLQDRT-UHFFFAOYSA-L 0.000 description 2
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 description 2
- SGGOJYZMTYGPCH-UHFFFAOYSA-L manganese(2+);naphthalene-2-carboxylate Chemical compound [Mn+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 SGGOJYZMTYGPCH-UHFFFAOYSA-L 0.000 description 2
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- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 2
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 description 2
- VILFVXYKHXVYAB-UHFFFAOYSA-N naphthalene-2,7-disulfonic acid Chemical compound C1=CC(S(O)(=O)=O)=CC2=CC(S(=O)(=O)O)=CC=C21 VILFVXYKHXVYAB-UHFFFAOYSA-N 0.000 description 2
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- 239000002667 nucleating agent Substances 0.000 description 2
- YJFCFSVVFTZXBL-UHFFFAOYSA-N o-[3-henicosanethioyloxy-2,2-bis(henicosanethioyloxymethyl)propyl] henicosanethioate Chemical compound CCCCCCCCCCCCCCCCCCCCC(=S)OCC(COC(=S)CCCCCCCCCCCCCCCCCCCC)(COC(=S)CCCCCCCCCCCCCCCCCCCC)COC(=S)CCCCCCCCCCCCCCCCCCCC YJFCFSVVFTZXBL-UHFFFAOYSA-N 0.000 description 2
- UTOPWMOLSKOLTQ-UHFFFAOYSA-N octacosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O UTOPWMOLSKOLTQ-UHFFFAOYSA-N 0.000 description 2
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- JFOJYGMDZRCSPA-UHFFFAOYSA-J octadecanoate;tin(4+) Chemical compound [Sn+4].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O JFOJYGMDZRCSPA-UHFFFAOYSA-J 0.000 description 2
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- VPPWQRIBARKZNY-UHFFFAOYSA-N oxo(diphenyl)tin Chemical compound C=1C=CC=CC=1[Sn](=O)C1=CC=CC=C1 VPPWQRIBARKZNY-UHFFFAOYSA-N 0.000 description 2
- SIWVEOZUMHYXCS-UHFFFAOYSA-N oxo(oxoyttriooxy)yttrium Chemical compound O=[Y]O[Y]=O SIWVEOZUMHYXCS-UHFFFAOYSA-N 0.000 description 2
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- 101150102492 pda1 gene Proteins 0.000 description 2
- TWBKZBJAVASNII-UHFFFAOYSA-N pentadecane-1-sulfonic acid Chemical compound CCCCCCCCCCCCCCCS(O)(=O)=O TWBKZBJAVASNII-UHFFFAOYSA-N 0.000 description 2
- WRZYZGACMDFTQX-UHFFFAOYSA-N pentane-2,4-dione tin(2+) Chemical compound [Sn+2].C(C)(=O)CC(C)=O WRZYZGACMDFTQX-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- IFFPHDYFQRRKPZ-UHFFFAOYSA-N phenol;titanium Chemical compound [Ti].OC1=CC=CC=C1.OC1=CC=CC=C1.OC1=CC=CC=C1.OC1=CC=CC=C1 IFFPHDYFQRRKPZ-UHFFFAOYSA-N 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- ODOPKAJVFRHHGM-UHFFFAOYSA-N phenyltin Chemical compound [Sn]C1=CC=CC=C1 ODOPKAJVFRHHGM-UHFFFAOYSA-N 0.000 description 2
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 2
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- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 2
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- 238000006068 polycondensation reaction Methods 0.000 description 2
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- RLEFZEWKMQQZOA-UHFFFAOYSA-M potassium;octanoate Chemical compound [K+].CCCCCCCC([O-])=O RLEFZEWKMQQZOA-UHFFFAOYSA-M 0.000 description 2
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- HKJYVRJHDIPMQB-UHFFFAOYSA-N propan-1-olate;titanium(4+) Chemical compound CCCO[Ti](OCCC)(OCCC)OCCC HKJYVRJHDIPMQB-UHFFFAOYSA-N 0.000 description 2
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- 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 2
- ZGSOBQAJAUGRBK-UHFFFAOYSA-N propan-2-olate;zirconium(4+) Chemical compound [Zr+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-] ZGSOBQAJAUGRBK-UHFFFAOYSA-N 0.000 description 2
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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 2
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- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- YIMHRDBSVCPJOV-UHFFFAOYSA-N n'-(2-ethoxyphenyl)-n-(2-ethylphenyl)oxamide Chemical compound CCOC1=CC=CC=C1NC(=O)C(=O)NC1=CC=CC=C1CC YIMHRDBSVCPJOV-UHFFFAOYSA-N 0.000 description 1
- KCZLICCXIBLZPN-UHFFFAOYSA-N n,n'-diethyl-n,n'-diphenyloxamide Chemical compound C=1C=CC=CC=1N(CC)C(=O)C(=O)N(CC)C1=CC=CC=C1 KCZLICCXIBLZPN-UHFFFAOYSA-N 0.000 description 1
- SUEGTUMFNUNYPW-UHFFFAOYSA-N n,n-diethyl-n',n'-diphenyloxamide Chemical compound C=1C=CC=CC=1N(C(=O)C(=O)N(CC)CC)C1=CC=CC=C1 SUEGTUMFNUNYPW-UHFFFAOYSA-N 0.000 description 1
- DIAIBWNEUYXDNL-UHFFFAOYSA-N n,n-dihexylhexan-1-amine Chemical compound CCCCCCN(CCCCCC)CCCCCC DIAIBWNEUYXDNL-UHFFFAOYSA-N 0.000 description 1
- OOHAUGDGCWURIT-UHFFFAOYSA-N n,n-dipentylpentan-1-amine Chemical compound CCCCCN(CCCCC)CCCCC OOHAUGDGCWURIT-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- NZZGQZMNFCTNAM-UHFFFAOYSA-N naphthalene-2,6-dicarbonyl chloride Chemical compound C1=C(C(Cl)=O)C=CC2=CC(C(=O)Cl)=CC=C21 NZZGQZMNFCTNAM-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 239000010449 novaculite Substances 0.000 description 1
- QJXZDBOIVBLYSJ-UHFFFAOYSA-N o-[3-heptadecanethioyloxy-2,2-bis(heptadecanethioyloxymethyl)propyl] heptadecanethioate Chemical compound CCCCCCCCCCCCCCCCC(=S)OCC(COC(=S)CCCCCCCCCCCCCCCC)(COC(=S)CCCCCCCCCCCCCCCC)COC(=S)CCCCCCCCCCCCCCCC QJXZDBOIVBLYSJ-UHFFFAOYSA-N 0.000 description 1
- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 description 1
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 1
- KCRLWVVFAVLSAP-UHFFFAOYSA-N octyl dihydrogen phosphite Chemical compound CCCCCCCCOP(O)O KCRLWVVFAVLSAP-UHFFFAOYSA-N 0.000 description 1
- YAFOVCNAQTZDQB-UHFFFAOYSA-N octyl diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)(OCCCCCCCC)OC1=CC=CC=C1 YAFOVCNAQTZDQB-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012788 optical film Substances 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000012785 packaging film Substances 0.000 description 1
- 229920006280 packaging film Polymers 0.000 description 1
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical compound CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
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- 150000004714 phosphonium salts Chemical class 0.000 description 1
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- LGRFSURHDFAFJT-UHFFFAOYSA-N phthalic anhydride Chemical compound C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920002530 polyetherether ketone Polymers 0.000 description 1
- 229920001601 polyetherimide Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
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- 229920006380 polyphenylene oxide Polymers 0.000 description 1
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- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000004300 potassium benzoate Substances 0.000 description 1
- 235000010235 potassium benzoate Nutrition 0.000 description 1
- 229940103091 potassium benzoate Drugs 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 229940114930 potassium stearate Drugs 0.000 description 1
- ANBFRLKBEIFNQU-UHFFFAOYSA-M potassium;octadecanoate Chemical compound [K+].CCCCCCCCCCCCCCCCCC([O-])=O ANBFRLKBEIFNQU-UHFFFAOYSA-M 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 229960000380 propiolactone Drugs 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
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- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
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- 235000012239 silicon dioxide Nutrition 0.000 description 1
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- 229920002050 silicone resin Polymers 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 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
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 229960003885 sodium benzoate Drugs 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 229940037312 stearamide Drugs 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
- RXSHXLOMRZJCLB-UHFFFAOYSA-L strontium;diacetate Chemical compound [Sr+2].CC([O-])=O.CC([O-])=O RXSHXLOMRZJCLB-UHFFFAOYSA-L 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
- 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
- 150000003512 tertiary amines Chemical class 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
- GUWLXCFSEPHWCL-UHFFFAOYSA-N tetradecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 GUWLXCFSEPHWCL-UHFFFAOYSA-N 0.000 description 1
- LVEOKSIILWWVEO-UHFFFAOYSA-N tetradecyl 3-(3-oxo-3-tetradecoxypropyl)sulfanylpropanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCC LVEOKSIILWWVEO-UHFFFAOYSA-N 0.000 description 1
- YMBCJWGVCUEGHA-UHFFFAOYSA-M tetraethylammonium chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC YMBCJWGVCUEGHA-UHFFFAOYSA-M 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
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- AYEKOFBPNLCAJY-UHFFFAOYSA-O thiamine pyrophosphate Chemical compound CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N AYEKOFBPNLCAJY-UHFFFAOYSA-O 0.000 description 1
- 239000012974 tin catalyst Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 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
- 150000003852 triazoles Chemical class 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-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
- MZHULIWXRDLGRR-UHFFFAOYSA-N tridecyl 3-(3-oxo-3-tridecoxypropyl)sulfanylpropanoate Chemical compound CCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCC MZHULIWXRDLGRR-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
- 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
- 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
- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 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
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
- 239000010456 wollastonite Substances 0.000 description 1
- 229910052882 wollastonite Inorganic materials 0.000 description 1
- VYXPIEPOZNGSJX-UHFFFAOYSA-L zinc;dioxido-oxo-phenyl-$l^{5}-phosphane Chemical compound [Zn+2].[O-]P([O-])(=O)C1=CC=CC=C1 VYXPIEPOZNGSJX-UHFFFAOYSA-L 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
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- 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
- 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
- C08G63/08—Lactones or lactides
-
- 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
- C08G63/78—Preparation processes
- C08G63/80—Solid-state polycondensation
-
- 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
- C08G63/78—Preparation processes
- C08G63/82—Preparation processes characterised by the catalyst used
-
- 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
- C08G63/78—Preparation processes
- C08G63/82—Preparation processes characterised by the catalyst used
- C08G63/823—Preparation processes characterised by the catalyst used for the preparation of polylactones or polylactides
-
- 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
- C08G63/91—Polymers modified by chemical after-treatment
- C08G63/912—Polymers modified by chemical after-treatment derived from hydroxycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
-
- 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
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/12—Copolymers
- C08G2261/126—Copolymers block
-
- 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
- C08L2205/025—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group containing two or more polymers of the same hierarchy C08L, and differing only in parameters such as density, comonomer content, molecular weight, structure
-
- 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
- C08L2205/05—Polymer mixtures characterised by other features containing polymer components which can react with one another
Landscapes
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Materials Engineering (AREA)
- Manufacturing & Machinery (AREA)
- Engineering & Computer Science (AREA)
- Polyesters Or Polycarbonates (AREA)
- Biological Depolymerization Polymers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
Sc=ΔHh/(ΔHl+ΔHh)×100 (1)
ここで、ΔHh:ステレオコンプレックス結晶に基づく熱量(J/g)、ΔHl: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)、
である。
本発明のポリ乳酸ブロック共重合体の製造方法は、得られるポリ乳酸ブロック共重合体が下記式(3)を満たすことが好ましい。
本発明のポリ乳酸ブロック共重合体の製造方法は、得られるポリ乳酸ブロック共重合体のDSC測定において、ポリ乳酸ブロック共重合体を250度まで昇温して3分間恒温状態にした後、冷却速度20℃/minで降温した際の降温結晶化温度が130℃以上であることが好ましい。
本発明においては、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以上であることが、高融点のポリ乳酸ステレオコンプレックスを形成しやすいポリ乳酸ブロック共重合体が得られる点で好ましい。さらに好ましくは5以上であり、7以上であることが特に好ましい。
(原料として用いるポリ乳酸の製造方法)
本発明において、原料として用いるL―乳酸単位からなるポリ−L−乳酸およびD−乳酸単位からなるポリ−D−乳酸の製造方法については、特に限定されるものではなく、一般のポリ乳酸の製造方法を利用することができる。具体的には、L−乳酸またはD−乳酸を原料として、一旦、環状2量体であるL−ラクチドまたはD−ラクチドを生成せしめ、その後、開環重合を行う2段階のラクチド法と、当該原料を溶媒中または非溶媒中で直接脱水縮合を行う1段階の直接重合法などが知られており、いずれの製法を利用してもよい。
(ポリ乳酸の混合方法)
次にポリ−L−乳酸とポリ−D−乳酸を混合する工程について説明する。
また、混合に用いるポリ−L−乳酸とポリ−D−乳酸の結晶化の有無については特に限定されず、結晶化したポリ−L−乳酸とポリ−D−乳酸を混合してもよいし、溶融状態のポリ−L−乳酸とポリ−D−乳酸を混合することもできる。混合に用いるポリ−L−乳酸とポリ−D−乳酸の結晶化を行う場合、具体的な方法として気相中または液相中において結晶化処理温度で保持する方法およびポリ−L−乳酸とポリ−D−乳酸の溶融混合物を延伸または剪断の操作を行いながら冷却固化させる方法などが挙げられ、操作が簡便であるという観点においては、気相中または液相中において結晶化処理温度で保持する方法が好ましい。
また、混合後におけるポリ−L−乳酸とポリ−D−乳酸の混合物の分散度は1.5〜4.0の範囲が好ましい。さらに好ましくは2.0〜3.7の範囲であり、特に好ましくは2.5〜3.5の範囲である。ここで、分散度とは、混合物の数平均分子量に対する重量平均分子量の割合のことをいい、具体的には溶媒としてヘキサフルオロイソプロパノールまたはクロロホルムを用いたゲルパーミエーションクロマトグラフィー(GPC)測定による標準ポリメチルメタクリレート換算の値である。
(固相重合)
次に、ポリ−L−乳酸とポリ−D−乳酸の混合物を固相重合する工程について説明する。この固相重合工程では、ポリ−L−乳酸とポリ−D−乳酸が、主に直接重合することによりポリ乳酸ブロック共重合体が得られる。
固相重合工程においては、混合物の分散度が小さくなることが好ましい。具体的には固相重合前の混合物の分散度が1.5〜4.0の範囲から固相重合後にはポリ乳酸ブロック共重合体の分散度が1.5〜2.7の範囲になることが好ましい。さらに好ましくは固相重合前の混合物の分散度が2.0〜3.7の範囲が固相重合後にはポリ乳酸ブロック共重合体の分散度が1.8〜2.6の範囲に小さくなることであり、特に好ましくは、固相重合前の混合物の分散度が2.5〜3.5の範囲から固相重合後にはポリ乳酸ブロック共重合体の分散度が2.0〜2.5の範囲になることである。
(ポリ乳酸ブロック共重合体)
本発明の製造方法により得られるポリ乳酸ブロック共重合体の重量平均分子量は、特に限定されるものではないが、10万以上30万未満の範囲であることが成形性および機械物性の点で好ましい。さらに好ましくは12万以上28万未満の範囲であり、14万以上26万未満の範囲であることが特に好ましい。また、ポリ乳酸ブロック共重合体の分散度は、1.5〜3.0の範囲が機械物性の点で好ましい。分散度の範囲は1.8〜2.7であることがさらに好ましく、2.0〜2.4であることが成形性および機械物性の点で特に好ましい。なお、重量平均分子量および分散度は、溶媒としてヘキサフルオロイソプロパノールまたはクロロホルムを用いたゲルパーミエーションクロマトグラフィー(GPC)測定による標準ポリメチルメタクリレート換算の値である。
本発明の製造方法により得られるポリ乳酸ブロック共重合体は、150℃〜190℃の範囲でポリ−L−乳酸単独結晶およびポリ−D−乳酸単独結晶に基づく融点を有し、また、ステレオコンプレックス形成によりステレオコンプレックス結晶に基づく融点を200〜230℃の範囲で有する。ステレオコンプレックス結晶由来の融点の好ましい範囲は205℃〜230℃であり、210℃〜230℃の温度範囲がさらに好ましく、215℃〜230℃の温度範囲が特に好ましい。原料として用いるポリ−L−乳酸(もしくはポリ−D−乳酸)に含まれる主成分のL−乳酸(もしくはD−乳酸)単位の量により結晶性を制御することが可能で、結晶性が高いほどステレオコンプレックス結晶由来の融点は上昇し、好ましい。例えば、ポリ−L−乳酸中に含まれる主成分のL−乳酸の好ましい範囲は前記のとおり、好ましくは80mol%であり、90mol%以上含有していることがより好ましく、95mol%以上含有していることがさらに好ましく、98mol%以上含有していることが特に好ましい。
本発明の製造方法により得られるポリ乳酸ブロック共重合体は、成形性および耐熱性に優れるという点で降温結晶化温度(Tc)が130℃以上であることが好ましい。ここで、成型体の降温結晶化温度(Tc)とは、示差走査熱量計(DSC)により昇温速度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したポリ乳酸結晶由来の結晶化温度である。結晶化温度(Tc)は、特に限定されるものではないが、耐熱性および透明性の観点から、130℃以上が好ましく、132℃以上がより好ましく、135℃以上が特に好ましい。
ここで、ΔHm:成形体の結晶融解エンタルピー(J/g)、ΔHc:成形体の昇温時結晶化エンタルピー(J/g)である。
本発明において得られるポリ乳酸ブロック共重合体を含む成形体に含まれるポリ乳酸ブロック共重合体は、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以上であることが、高融点のポリ乳酸ステレオコンプレックスを形成しやすいポリ乳酸ブロック共重合体が得られる点で好ましい。また、1セグメントあたりの分子量は2千〜5万であることが好ましい。さらに好ましくは、4千〜4.5万であり、5千〜4万であることが機械物性の点で特に好ましい。
本発明のポリ乳酸ブロック共重合体の製造方法において、得られるポリ乳酸ブロック共重合体を含む成形体に含まれるポリ乳酸ブロック共重合体の重量平均分子量は、特に限定されるものではないが、機械物性の点で10万以上30万未満であることが好ましい。12万以上28万未満であることがさらに好ましく、14万以上26万未満であることが成形性および機械物性の点で特に好ましい。また、本発明において得られるポリ乳酸ブロック共重合体を含む成形体に含まれるポリ乳酸ブロック共重合体の分散度は、1.5〜3.0の範囲が機械物性の点で好ましい。分散度の範囲が1.8〜2.7であることがさらに好ましく、2.0〜2.4であることが成形性および機械物性の点で特に好ましい。なお、重量平均分子量および分散度とは、溶媒としてヘキサフルオロイソプロパノールまたはクロロホルムを用いたゲルパーミエーションクロマトグラフィー(GPC)測定による標準ポリメチルメタクリレート換算の値である。
(1)分子量および分散度
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の測定は、検出器にWATERS社示差屈折計WATERS410を用い、ポンプにWATERS社MODEL510を用い、カラムにShodex GPC HFIP-806MとShodex GPC HFIP-LG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、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)融点、融解温度および融解熱量
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示差走査型熱量計(DSC)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℃/minである。
(3)ステレオコンプレックス形成率(Sc)
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)のステレオコンプレックス形成率(Sc)は、下記式(12)から算出した。
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。
(4)ポリマーの収率
ポリ乳酸ブロック共重合体の収率(Y)は、下記式(13)から算出した。
但し、固相重合前の混合物重量をWp、固相重合後のポリ乳酸ブロック共重合体の重量をWsとする。
(5)ポリマーの降温結晶化温度
ポリ乳酸ブロック共重合体およびポリ−L−乳酸とポリ−D−乳酸の混合物の降温結晶化温度は、パーキンエルマー社示差走査型熱量計(DSC)により測定した。具体的には、試料5mgを示差走査熱量計(DSC)により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。
(6)相対結晶化度
ポリ乳酸ブロック共重合体およびポリ−L−乳酸とポリ−D−乳酸の混合物の相対結晶化度は、パーキンエルマー社示差走査型熱量計(DSC)により成形体中のポリ−L−乳酸単独結晶およびポリ−D−乳酸単独結晶由来の融解エンタルピーとステレオコンプレックス結晶融解エンタルピーの合計ΔHmと、成形体の昇温時の結晶化エンタルピーΔHcをそれぞれ測定し、下記式(14)から算出した。
(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0.1mm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)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0.1mm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(セイコーインストルメンツ製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0.1mm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0.1mm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。
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。
[参考例1]
撹拌装置と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時間重合反応を行い、ポリ−L−乳酸(PLA1)を得た。PLA1の重量平均分子量は1.8万、分散度は1.5、融点は149℃、融解終了温度は163℃であった。
[参考例2]
参考例1で得られたPLA1を、窒素雰囲気下110℃で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(PLA2)を得た。PLA2の重量平均分子量は4.3万、分散度は1.8、融点は159℃、融解終了温度は176℃であった。
[参考例3]
参考例1で得られたPLA1を、窒素雰囲気下110℃で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12時間固相重合を行い、ポリ−L−乳酸(PLA3)を得た。PLA3の重量平均分子量は13.7万、分散度は1.8、融点は168℃、融解終了温度は189℃であった。
[参考例4]
参考例1で得られたPLA1を、窒素雰囲気下110℃で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−L−乳酸(PLA4)を得た。PLA4の重量平均分子量は20.3万、分散度は1.9、融点は170℃、融解終了温度は189℃であった。
[参考例5]
撹拌装置を備えた反応容器中に、L−ラクチドを50部入れ、窒素雰囲気下、120℃で均一に溶解させた後、温度を150℃にし、オクチル酸錫(II)0.003部を添加して2時間反応させることにより、ポリ−L−乳酸(PLA5)を得た。PLA5の重量平均分子量は26.2万、分散度は2.1、融点は171℃、融解終了温度は191℃であった。
[参考例6]
90wt%のL−乳酸水溶液1kgを150℃、4,000Paで6時間撹拌しながら水を留出させてオリゴマー化した。このオリゴマーに塩化第一錫0.2gとp−トルエンスルホン酸0.2gとを添加し、180℃、1,300Paで6時間溶融重合を行うことによりポリ−L−乳酸プレポリマーを得た。このプレポリマーの固体を粉砕し、140℃で30時間固相重合することによりポリ−L−乳酸(PLA6)を得た。PLA6の重量平均分子量は15.4万、分散度は2.6、融点は172℃、融解終了温度は194℃であった。
[参考例7]
重合反応触媒を酢酸錫(II)0.02部およびメタンスルホン酸0.13部に変更する以外は参考例1と同様の方法にて重合反応を行い、ポリ−L−乳酸(PLA7)を得た。PLA7の重量平均分子量は1.9万、分散度は1.5、融点は150℃、融解終了温度は164℃であった。
[参考例8]
参考例1で得られたPLA7を、窒素雰囲気下110℃で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12時間固相重合を行い、ポリ−L−乳酸(PLA8)を得た。PLA8の重量平均分子量は14.0万、分散度は1.8、融点は169℃、融解終了温度は189℃であった。
[参考例9]
参考例1で得られたPLA7を、窒素雰囲気下110℃で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12時間固相重合を行い、ポリ−L−乳酸(PLA9)を得た。PLA9の重量平均分子量は22.1万、分散度は1.8、融点は170℃、融解終了温度は191℃であった。
[参考例10]
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時間重合反応を行い、ポリ−D−乳酸(PDA1)を得た。PDA1の重量平均分子量は1.5万、分散度は1.5、融点は147℃、融解終了温度は163℃であった。
[参考例11]
参考例7で得られたPDA1を、窒素雰囲気下110℃で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3時間固相重合を行い、ポリ−D−乳酸(PDA2)を得た。PDA2の重量平均分子量は2.9万、分散度は1.6、融点は150℃、融解終了温度は168℃であった。
[参考例12]
参考例7で得られたPDA1を、窒素雰囲気下110℃で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6時間固相重合を行い、ポリ−D−乳酸(PDA3)を得た。PDA3の重量平均分子量は4.2万、分散度は1.6、融点は158℃、融解終了温度は176℃であった。
[参考例13]
参考例7で得られたPDA1を、窒素雰囲気下110℃で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−D−乳酸(PDA4)を得た。PDA4の重量平均分子量は19.8万、分散度は2.0、融点は170℃、融解終了温度は191℃であった。
[参考例14]
90wt%のD−乳酸水溶液1kgを150℃、4,000Paで6時間撹拌しながら水を留出させてオリゴマー化した。このオリゴマーに塩化第一錫0.2gとp−トルエンスルホン酸0.2gとを添加し、180℃、1,300Paで3時間溶融重合を行うことによりポリ−L−乳酸(PDA5)を得た。PDA5の重量平均分子量は1.6万、分散度は1.5、融点は144℃、融解終了温度は160℃であった。
[参考例15]
重合反応触媒を酢酸錫(II)0.02部およびメタンスルホン酸0.13部に変更する以外は参考例10と同様の方法にて重合反応を行い、ポリ−D−乳酸(PDA6)を得た。PDA6の重量平均分子量は1.6万、分散度は1.5、融点は149℃、融解終了温度は162℃であった。
[参考例16]
参考例15で得られたPDA6を、窒素雰囲気下110℃で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3時間固相重合を行い、ポリ−D−乳酸(PDA7)を得た。PDA7の重量平均分子量は3.1万、分散度は1.6、融点は152℃、融解終了温度は170℃であった。
[参考例17]
参考例15で得られたPDA6を、窒素雰囲気下110℃で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6時間固相重合を行い、ポリ−D−乳酸(PDA8)を得た。PDA8の重量平均分子量は5.0万、分散度は1.6、融点は160℃、融解終了温度は177℃であった。
[参考例18]
参考例7で得られたPDA6を、窒素雰囲気下110℃で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−D−乳酸(PDA9)を得た。PDA9の重量平均分子量は20.4万、分散度は2.0、融点は172℃、融解終了温度は193℃であった。
(実施例1、2、4、6〜12、参考実施例3、5、比較例1〜5)
(1)ポリ−L−乳酸とポリ−D−乳酸を混合する工程
ポリ−L−乳酸とポリ−D−乳酸の混合は日本製鋼所社製TEX30型二軸押出機(L/D=45.5)を用いて行った。
(1)により得られた混合物を、真空乾燥機中、140℃にて圧力13.3Paで4時間固相重合を行い、次いで150℃に昇温して4時間、さらに160℃に昇温して10時間固相重合を行った。
(比較例6)
(1)ポリ−L−乳酸とポリ−D−乳酸を混合する工程
30gのPLA6と30gのPDA5を、200ccフラスコ中でブレンドしながら常圧で加熱し、室温から190℃まで10分間で昇温させた。昇温過程において160℃で一部の融解が確認された。その後、降温させ混合物を得た。
(1)で得られた混合物を圧力66.6Pa、110℃で2時間熱処理を行った後、130℃で5時間、140℃で25時間(合計30時間)加熱し固相重合を行った。
(比較例7)
(1)ポリ−L−乳酸とポリ−D−乳酸を混合する工程
ポリ−L−乳酸とポリ−D−乳酸の混合方法は実施例1と同様である。
L−ラクチド100部、エチレングリコール0.05部を撹拌装置のついた反応容器中で、窒素雰囲気下、150℃で均一に溶解させた後、オクチル酸錫0.003部を加え、3時間重合反応を行った。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(クロロホルムの5倍量)中で撹拌しながら沈殿させ、モノマーを完全に除去することでポリ−L−乳酸(PLA10)を得た。PLA10の重量平均分子量は20.1万、分散度は1.7、融点は173℃、融解終了温度は190℃であった。
[参考例20]
L−ラクチド100部、エチレングリコール0.1部を撹拌装置のついた反応容器中で、窒素雰囲気下、150℃で均一に溶解させた後、オクチル酸錫0.003重量部を加え、3時間重合反応を行った。その後、反応系内にリン系の触媒失活剤を0.01部添加して10分間撹拌を行い、触媒失活を行った。得られた反応物はクロロホルムに溶解させ、メタノール(クロロホルムの5倍量)中で撹拌しながら沈殿させ、モノマーを完全に除去することでポリ−L−乳酸(PLA11)を得た。PLA11の重量平均分子量は12.2万、分散度は1.7、融点は170℃、融解終了温度188℃であった。
[参考例21]
D−ラクチド100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0.003部を加え、6時間重合反応を行った。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(クロロホルムの5倍量)中で撹拌しながら沈殿させ、モノマーを完全に除去することでポリ−D−乳酸(PDA10)を得た。PDA10の重量平均分子量は130万、分散度は1.6、融点は180℃、融解終了温度194℃であった。
[参考例22]
D−ラクチド100部,エチレングリコール0.05部を撹拌装置のついた反応容器中で、窒素雰囲気下、150℃で均一に溶解させた後、オクチル酸錫0.003部を加え、3時間重合反応を行った。重合終了後、反応物をクロロホルムに溶解させ、メタノール(クロロホルムの5倍量)中で撹拌しながら沈殿させ、モノマーを完全に除去することでポリ−D−乳酸(PDA11)を得た。PDA11の重量平均分子量は19.8万、分散度は1.7、融点は172℃、融解終了温度190℃であった。
[参考例23]
D−ラクチド100部,エチレングリコール0.1部を撹拌装置のついた反応容器中で、窒素雰囲気下、150℃で均一に溶解させた後、オクチル酸錫0.003部を加え、3時間重合反応を行った。その後、反応系内にリン系の触媒失活剤を0.01部添加して10分間撹拌を行い、触媒失活を行った。得られた反応物をクロロホルムに溶解させ、メタノール(クロロホルムの5倍量)中で撹拌しながら沈殿させ、モノマーを完全に除去することでポリ−D−乳酸(PDA12)を得た。PDA12の重量平均分子量は12.0万、分散度は1.7、融点は169℃、融解終了温度188℃であった。
(比較例8、9、11、12)
(1)ポリ−L−乳酸とポリ−D−乳酸を混合する工程
ポリ−L−乳酸とポリ−D−乳酸の混合は東洋精機製バッチ式二軸混練機(ラボプラストミル)を用いて行い、ポリ乳酸混合物を得た。試験条件は、混練温度245℃、混練回転数120rpm、混練時間は比較例8、11が10分、比較例9、12が60分である。ポリ−L−乳酸とポリ−D−乳酸の組み合わせは表2に示すとおりである。
(比較例10、13)
(1)ポリ−L−乳酸とポリ−D−乳酸を混合する工程
ポリ乳酸混合物は、比較例9、12と同様条件でバッチ式二軸混練機を用いてポリ−L−乳酸とポリ−D−乳酸を60分間混練し、混練後可塑剤を10重量部添加してさらに5分間混練することで作製した。ポリ−L−乳酸、ポリ−D−乳酸、可塑剤の組み合わせは表2に示すとおりである。
(比較例14〜17)
(1)ポリ−L−乳酸とポリ−D−乳酸を混合する工程
ポリ−L−乳酸とポリ−D−乳酸の混合は、実施例1、2、4、6〜12、参考実施例3、5と同様二軸押出機を用いて混練により作製した。二軸押出機に対するポリ−L−乳酸、ポリ−D−乳酸および結晶核剤の供給に関しては、いずれも樹脂供給口から行い、混練温度は240℃に設定し、混練を行った。ポリ−L−乳酸、ポリ−D−乳酸および結晶核剤の組み合わせは表2に示すとおりである。
表3に示すとおり、実施例1、2、4、6〜12、参考実施例3、5と比較例1〜6で得られたポリ乳酸ブロック共重合体(SB1〜SB12、SB13〜SB18)および比較例7で得られたポリ乳酸混合物(SB19)を、二軸押出機を用いてリン系触媒失活剤0.05部とともに240℃での溶融混練を行い、触媒失活を行った。続いて、240℃で2分間加熱して溶融し、その後プレス温度80℃でプレスすることで厚さ0.1mmのプレスシートを作製した。次いで、プレスシートを窒素雰囲気下、110℃で30分間の熱処理条件にて熱処理を行うことで各種測定用のシート状成形体とした。
(実施例25)
実施例1で固相重合により得られたポリ乳酸ブロック共重合体SB1について、シート成形体を作製する前に触媒失活を行った。触媒失活の方法は実施例13、14、16、18〜24、参考実施例15、17と同様である。続いて、触媒失活を行ったポリ乳酸ブロック共重合体は、240℃で2分間加熱して溶融し、その後プレス温度80℃でプレスすることで厚さ0.1mmのプレスシート作製した後、氷水中に冷却することで各種測定用のシート状成形体とした。シート状成形体の各種物性測定方法は実施例13、14、16、18〜24、参考実施例15、17と同様である。
(比較例25)
実施例1で得られたポリ乳酸混合物SC1について、シート成形体を作製する前に触媒失活を行った。触媒失活の方法は実施例13、14、16、18〜24、参考実施例15、17と同様である。続いて触媒失活したSC1を用いて各種物性測定用の成形体を作製した。成形体製造方法および物性測定方法は実施例13、14、16、18〜24、参考実施例15、17と同様である。
(比較例26、27、29、30)
比較例8、9、11、12で得られたポリ乳酸混合物(SC19、SC20、SC22、SC23)について、シート成形体を作製する前に触媒失活を行った。触媒失活の方法は実施例13、14、16、18〜24、参考実施例15、17と同様である。続いて触媒失活したポリ乳酸混合物を用いて各種物性測定用の成形体を作製した。各種物性測定用の成形体作製方法、物性測定方法は実施例13、14、16、18〜24、参考実施例15、17と同様である。
(比較例28、31)
比較例10、13で得られたポリ乳酸混合物(SC21、SC24)について、シート成形体を作製する前に触媒失活を行った。触媒失活の方法は実施例13、14、16、18〜24、参考実施例15、17と同様である。続いて触媒失活したポリ乳酸混合物を用いて各種物性測定用の成形体を作製した。各種物性測定用の成形体の製造方法および物性測定方法は実施例13、14、16、18〜24、参考実施例15、17と同様である。表3に示すとおり、各比較例のシート状成形体の相対結晶化度はいずれも100%であった。成形体のヘイズ値は、可塑剤を添加することで比較例23、25に比較して低くなり、その結果透明性が向上したが、成形体の引張強度については可塑剤添加により低下する傾向であった。
(比較例32〜36)
参考例20で得られたポリ乳酸(PLA11)および比較例14〜17で得られたポリ乳酸混合物(SC25〜SC28)について、シート成形体を作製する前に触媒失活を行った。触媒失活の方法は実施例13、14、16、18〜24、参考実施例15、17と同様である。続いて触媒失活したポリ乳酸混合物を用いて各種物性測定用の成形体を作製した。
Claims (11)
- 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6万〜30万であり、もう一方の重量平均分子量が1万〜5万であるポリ−L−乳酸とポリ−D−乳酸を混合し、重量平均分子量が9万以上、かつ下記式(1)に示すステレオコンプレックス形成率(Sc)が60%を超え99%までの範囲である混合物を得る工程、次いで、混合物を混合物の融点より低い温度で固相重合する工程からなるL−乳酸単位からなるセグメントとD−乳酸単位からなるセグメントにより構成されるポリ乳酸ブロック共重合体の製造方法。
Sc=ΔHh/(ΔHl+ΔHh)×100 (1)
ここで、ΔHh:ステレオコンプレックス結晶に基づく熱量(J/g)、ΔHl: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) - 原料となるポリ−L−乳酸とポリ−D−乳酸のいずれか一方の重量平均/分子量が17万以上であり、かつもう一方の重量平均分子量が2万以上である請求項1記載のポリ乳酸ブロック共重合体の製造方法。
- ポリ−L−乳酸とポリ−D−乳酸の混合物が、下記式(2)に示すステレオコンプレックス形成率(Sc)が70%を超え95%までの範囲である請求項1または2記載のポリ乳酸ブロック共重合体の製造方法。
Sc=ΔHh/(ΔHl+ΔHh)×100 (2) - 得られるポリ乳酸ブロック共重合体が下記式(3)を満たす請求項1〜3いずれかに記載のポリ乳酸ブロック共重合体の製造方法。
Sc=ΔHh/(ΔHl+ΔHh)×100>80 (3) - 得られるポリ乳酸ブロック共重合体のDSC測定において、ポリ乳酸ブロック共重合体を250度まで昇温して3分間恒温状態にした後、冷却速度20℃/minで降温した際の降温結晶化温度が130℃以上である請求項1〜4いずれかに記載のポリ乳酸ブロック共重合体の製造方法。
- 得られるポリ乳酸ブロック共重合体の重量平均分子量と数平均分子量の比で示される分散度が2.7以下である請求項1〜5いずれかに記載のポリ乳酸ブロック共重合体の製造方法。
- 混合物に含まれる触媒が、混合物100重量部に対して0.001〜0.5重量部である請求項1〜6いずれかに記載のポリ乳酸ブロック共重合体の製造方法。
- 混合物に含まれる触媒が錫化合物、チタン化合物、鉛化合物、亜鉛化合物、コバルト化合物、鉄化合物、リチウム化合物、希土類化合物、およびスルホン酸化合物から得られる少なくとも一種である請求項7に記載のポリ乳酸ブロック共重合体の製造方法。
- 錫化合物が、酢酸錫(II)、オクチル酸錫(II)、塩化錫(II)、塩化錫(IV)から選ばれる少なくとも一種であり、スルホン酸化合物がメタンスルホン酸、エタンスルホン酸、プロパンスルホン酸、プロパンジスルホン酸、ナフタレンジスルホン酸、および2−アミノエタンスルホン酸から選ばれる少なくとも一種である請求項8記載のポリ乳酸ブロック共重合体の製造方法。
- 固相重合時の温度を段階的または連続的に昇温する請求項1〜9いずれかに記載のポリ乳酸ブロック共重合体の製造方法。
- 得られるポリ乳酸ブロック共重合体の重量平均分子量が10万以上である請求項1〜10いずれかに記載のポリ乳酸ブロック共重合体の製造方法。
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KR20130113332A (ko) | 2013-10-15 |
EP2612878A4 (en) | 2017-04-05 |
BR112013002442A2 (pt) | 2016-05-24 |
TW201213400A (en) | 2012-04-01 |
US9150690B2 (en) | 2015-10-06 |
US20130158209A1 (en) | 2013-06-20 |
JP5957885B2 (ja) | 2016-07-27 |
WO2012029393A1 (ja) | 2012-03-08 |
EP2612877B1 (en) | 2018-03-21 |
CN103068881B (zh) | 2015-11-25 |
WO2012029392A1 (ja) | 2012-03-08 |
CN103068880B (zh) | 2015-11-25 |
BR112013001850A2 (pt) | 2016-05-31 |
EP2612878B1 (en) | 2018-07-18 |
CN103068880A (zh) | 2013-04-24 |
US20130165601A1 (en) | 2013-06-27 |
TW201213390A (en) | 2012-04-01 |
JPWO2012029392A1 (ja) | 2013-10-28 |
JPWO2012029393A1 (ja) | 2013-10-28 |
EP2612877A1 (en) | 2013-07-10 |
CN103068881A (zh) | 2013-04-24 |
EP2612877A4 (en) | 2017-06-21 |
KR20130118214A (ko) | 2013-10-29 |
EP2612878A1 (en) | 2013-07-10 |
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