CN101302284B - 一种高分子量高性能化聚乳酸的制备方法 - Google Patents
一种高分子量高性能化聚乳酸的制备方法 Download PDFInfo
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- CN101302284B CN101302284B CN2008100508615A CN200810050861A CN101302284B CN 101302284 B CN101302284 B CN 101302284B CN 2008100508615 A CN2008100508615 A CN 2008100508615A CN 200810050861 A CN200810050861 A CN 200810050861A CN 101302284 B CN101302284 B CN 101302284B
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- pla
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- lactic acid
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- 239000004626 polylactic acid Substances 0.000 title claims abstract description 56
- 238000002360 preparation method Methods 0.000 title claims abstract description 21
- 229920000747 poly(lactic acid) Polymers 0.000 title abstract description 51
- 238000006243 chemical reaction Methods 0.000 claims abstract description 41
- 239000012948 isocyanate Substances 0.000 claims abstract description 18
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 18
- 230000035484 reaction time Effects 0.000 claims abstract description 10
- 230000001588 bifunctional effect Effects 0.000 claims abstract description 6
- 239000000463 material Substances 0.000 claims abstract description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 32
- 150000002148 esters Chemical class 0.000 claims description 20
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 20
- -1 polyoxyethylene Polymers 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- JVTAAEKCZFNVCJ-REOHCLBHSA-N L-lactic acid Chemical compound C[C@H](O)C(O)=O JVTAAEKCZFNVCJ-REOHCLBHSA-N 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
- 239000004310 lactic acid Substances 0.000 claims description 10
- 235000014655 lactic acid Nutrition 0.000 claims description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 8
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000008393 encapsulating agent Substances 0.000 claims description 7
- 239000000178 monomer Substances 0.000 claims description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 claims description 6
- 238000007789 sealing Methods 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 238000006068 polycondensation reaction Methods 0.000 claims description 5
- 238000006116 polymerization reaction Methods 0.000 claims description 5
- 239000003381 stabilizer Substances 0.000 claims description 5
- 229930182843 D-Lactic acid Natural products 0.000 claims description 4
- JVTAAEKCZFNVCJ-UWTATZPHSA-N D-lactic acid Chemical compound C[C@@H](O)C(O)=O JVTAAEKCZFNVCJ-UWTATZPHSA-N 0.000 claims description 4
- 208000005156 Dehydration Diseases 0.000 claims description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 4
- 229910021626 Tin(II) chloride Inorganic materials 0.000 claims description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 4
- 230000018044 dehydration Effects 0.000 claims description 4
- 238000006297 dehydration reaction Methods 0.000 claims description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 235000011150 stannous chloride Nutrition 0.000 claims description 4
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 claims description 4
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 3
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 claims description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 3
- WHIVNJATOVLWBW-UHFFFAOYSA-N n-butan-2-ylidenehydroxylamine Chemical compound CCC(C)=NO WHIVNJATOVLWBW-UHFFFAOYSA-N 0.000 claims description 3
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 claims description 3
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims description 3
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 3
- ZXHZWRZAWJVPIC-UHFFFAOYSA-N 1,2-diisocyanatonaphthalene Chemical compound C1=CC=CC2=C(N=C=O)C(N=C=O)=CC=C21 ZXHZWRZAWJVPIC-UHFFFAOYSA-N 0.000 claims description 2
- UIMPAOAAAYDUKQ-UHFFFAOYSA-N 1-methoxy-4-(4-methoxyphenyl)benzene Chemical group C1=CC(OC)=CC=C1C1=CC=C(OC)C=C1 UIMPAOAAAYDUKQ-UHFFFAOYSA-N 0.000 claims description 2
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 claims description 2
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 claims description 2
- RFCQDOVPMUSZMN-UHFFFAOYSA-N 2-Naphthalenethiol Chemical compound C1=CC=CC2=CC(S)=CC=C21 RFCQDOVPMUSZMN-UHFFFAOYSA-N 0.000 claims description 2
- VSAWBBYYMBQKIK-UHFFFAOYSA-N 4-[[3,5-bis[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-2,4,6-trimethylphenyl]methyl]-2,6-ditert-butylphenol Chemical compound CC1=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C1CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 VSAWBBYYMBQKIK-UHFFFAOYSA-N 0.000 claims description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 2
- KXBFLNPZHXDQLV-UHFFFAOYSA-N [cyclohexyl(diisocyanato)methyl]cyclohexane Chemical compound C1CCCCC1C(N=C=O)(N=C=O)C1CCCCC1 KXBFLNPZHXDQLV-UHFFFAOYSA-N 0.000 claims description 2
- PXAJQJMDEXJWFB-UHFFFAOYSA-N acetone oxime Chemical compound CC(C)=NO PXAJQJMDEXJWFB-UHFFFAOYSA-N 0.000 claims description 2
- 229960001701 chloroform Drugs 0.000 claims description 2
- 229940022769 d- lactic acid Drugs 0.000 claims description 2
- 238000004821 distillation Methods 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 125000002462 isocyano group Chemical group *[N+]#[C-] 0.000 claims description 2
- 239000000395 magnesium oxide Substances 0.000 claims description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 2
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims description 2
- 238000010907 mechanical stirring Methods 0.000 claims description 2
- 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 claims description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 2
- TZMFJUDUGYTVRY-UHFFFAOYSA-N pentane-2,3-dione Chemical compound CCC(=O)C(C)=O TZMFJUDUGYTVRY-UHFFFAOYSA-N 0.000 claims description 2
- 229920001451 polypropylene glycol Polymers 0.000 claims description 2
- 238000000247 postprecipitation Methods 0.000 claims description 2
- 239000012453 solvate Substances 0.000 claims description 2
- 238000000967 suction filtration Methods 0.000 claims description 2
- 238000001291 vacuum drying Methods 0.000 claims description 2
- 238000005303 weighing Methods 0.000 claims description 2
- 239000011787 zinc oxide Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 14
- 239000004970 Chain extender Substances 0.000 abstract description 8
- 238000012643 polycondensation polymerization Methods 0.000 abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 6
- 230000003301 hydrolyzing effect Effects 0.000 abstract description 4
- 238000003860 storage Methods 0.000 abstract description 3
- 229920000570 polyether Polymers 0.000 abstract description 2
- 206010016275 Fear Diseases 0.000 abstract 1
- 239000004721 Polyphenylene oxide Substances 0.000 abstract 1
- 238000010924 continuous production Methods 0.000 abstract 1
- 150000002009 diols Chemical class 0.000 abstract 1
- 238000011031 large-scale manufacturing process Methods 0.000 abstract 1
- 238000005580 one pot reaction Methods 0.000 abstract 1
- 239000000565 sealant Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 description 8
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 8
- 238000002156 mixing Methods 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 239000003963 antioxidant agent Substances 0.000 description 6
- 230000003078 antioxidant effect Effects 0.000 description 6
- 230000005494 condensation Effects 0.000 description 5
- JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 3
- 150000003384 small molecules Chemical group 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 229920006158 high molecular weight polymer Polymers 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 206010023126 Jaundice Diseases 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006210 cyclodehydration reaction Methods 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
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- Polyurethanes Or Polyureas (AREA)
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CN2008100508615A CN101302284B (zh) | 2008-06-23 | 2008-06-23 | 一种高分子量高性能化聚乳酸的制备方法 |
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CN2008100508615A CN101302284B (zh) | 2008-06-23 | 2008-06-23 | 一种高分子量高性能化聚乳酸的制备方法 |
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CN101302284A CN101302284A (zh) | 2008-11-12 |
CN101302284B true CN101302284B (zh) | 2011-11-23 |
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Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20120095169A1 (en) * | 2009-06-30 | 2012-04-19 | Ryohei Ogawa | Polylactic acid-based resin, process for producing polylactic acid-based resin, polylactic acid resin composition, stereocomplex polylactic acid resin composition and process for producing stereocomplex polylactic acid resin composition |
CN101899139B (zh) * | 2010-07-23 | 2012-02-29 | 同济大学 | 一种聚乳酸基高弹性共聚物的制备方法 |
US9499658B2 (en) * | 2010-11-08 | 2016-11-22 | Young-Man Yoo | Polylactic acid resin, preparation method thereof, and packing film comprising the same |
US8829097B2 (en) | 2012-02-17 | 2014-09-09 | Andersen Corporation | PLA-containing material |
CN103881222B (zh) * | 2014-02-19 | 2017-05-03 | 深圳职业技术学院 | 塑料发泡材料及其制备方法 |
CN105175676B (zh) * | 2015-10-14 | 2018-01-02 | 中国科学院宁波材料技术与工程研究所 | 医疗输注器械用聚乳酸基聚氨酯弹性体材料及其制备方法 |
CN107060272B (zh) * | 2017-04-27 | 2023-09-29 | 福州皇家地坪有限公司 | 热固型预制磨石系统 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1537636A (zh) * | 2003-10-13 | 2004-10-20 | 四川大学华西药学院 | 药用高分子mPEG-PLGA-mPEG辅料及制法和应用 |
CN1563138A (zh) * | 2004-03-25 | 2005-01-12 | 同济大学 | 本体聚合制备高支化聚乳酸的方法 |
US20050036946A1 (en) * | 2003-08-11 | 2005-02-17 | Pathak Chandrashekhar P. | Radio-opaque compounds, compositions containing same and methods of their synthesis and use |
CN101024696A (zh) * | 2007-02-13 | 2007-08-29 | 四川大学 | 一种聚乳酸嵌段共聚物及其制备方法 |
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Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
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US20050036946A1 (en) * | 2003-08-11 | 2005-02-17 | Pathak Chandrashekhar P. | Radio-opaque compounds, compositions containing same and methods of their synthesis and use |
CN1537636A (zh) * | 2003-10-13 | 2004-10-20 | 四川大学华西药学院 | 药用高分子mPEG-PLGA-mPEG辅料及制法和应用 |
CN1563138A (zh) * | 2004-03-25 | 2005-01-12 | 同济大学 | 本体聚合制备高支化聚乳酸的方法 |
CN101024696A (zh) * | 2007-02-13 | 2007-08-29 | 四川大学 | 一种聚乳酸嵌段共聚物及其制备方法 |
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