CN1563139A - 一种直接熔融制备高分子量聚乳酸的方法 - Google Patents
一种直接熔融制备高分子量聚乳酸的方法 Download PDFInfo
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- CN1563139A CN1563139A CN 200410017212 CN200410017212A CN1563139A CN 1563139 A CN1563139 A CN 1563139A CN 200410017212 CN200410017212 CN 200410017212 CN 200410017212 A CN200410017212 A CN 200410017212A CN 1563139 A CN1563139 A CN 1563139A
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- Prior art keywords
- lactic acid
- reaction
- poly
- molecular weight
- chainextender
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- 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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Links
- 239000004626 polylactic acid Substances 0.000 title claims description 15
- 229920000747 poly(lactic acid) Polymers 0.000 title description 35
- 238000007500 overflow downdraw method Methods 0.000 title 1
- 239000004970 Chain extender Substances 0.000 claims abstract description 19
- 238000000034 method Methods 0.000 claims abstract description 18
- 238000006068 polycondensation reaction Methods 0.000 claims abstract description 14
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 9
- 125000000524 functional group Chemical group 0.000 claims abstract description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 9
- -1 isocyano- Chemical group 0.000 claims description 54
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 40
- 238000006243 chemical reaction Methods 0.000 claims description 29
- 235000014655 lactic acid Nutrition 0.000 claims description 20
- 239000004310 lactic acid Substances 0.000 claims description 20
- 230000018044 dehydration Effects 0.000 claims description 10
- 238000006297 dehydration reaction Methods 0.000 claims description 10
- 230000035484 reaction time Effects 0.000 claims description 10
- 230000004927 fusion Effects 0.000 claims description 7
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 4
- 239000011261 inert gas Substances 0.000 claims description 4
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical group O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 claims description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 229910021626 Tin(II) chloride Inorganic materials 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 230000006837 decompression Effects 0.000 claims description 3
- 239000007789 gas Substances 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 229910001510 metal chloride Inorganic materials 0.000 claims description 3
- 229910044991 metal oxide Inorganic materials 0.000 claims description 3
- 150000004706 metal oxides Chemical class 0.000 claims description 3
- 235000011150 stannous chloride Nutrition 0.000 claims description 3
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical group [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 claims description 3
- SJHPCNCNNSSLPL-CSKARUKUSA-N (4e)-4-(ethoxymethylidene)-2-phenyl-1,3-oxazol-5-one Chemical compound O1C(=O)C(=C/OCC)\N=C1C1=CC=CC=C1 SJHPCNCNNSSLPL-CSKARUKUSA-N 0.000 claims description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 2
- QJDGQRSDUWBFJB-UHFFFAOYSA-N 2-hydroxypropanoic acid;tin Chemical compound [Sn].CC(O)C(O)=O QJDGQRSDUWBFJB-UHFFFAOYSA-N 0.000 claims description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 2
- 229910021623 Tin(IV) bromide Inorganic materials 0.000 claims description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- 150000008065 acid anhydrides Chemical group 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 239000004411 aluminium Substances 0.000 claims description 2
- 229910052782 aluminium Inorganic materials 0.000 claims description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims description 2
- 150000003851 azoles Chemical class 0.000 claims description 2
- 150000007942 carboxylates Chemical class 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 229910052729 chemical element Inorganic materials 0.000 claims description 2
- 150000001924 cycloalkanes Chemical class 0.000 claims description 2
- 125000003700 epoxy group Chemical group 0.000 claims description 2
- 239000011521 glass Substances 0.000 claims description 2
- 239000003456 ion exchange resin Substances 0.000 claims description 2
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 2
- 239000012188 paraffin wax Substances 0.000 claims description 2
- 230000000737 periodic effect Effects 0.000 claims description 2
- 239000002994 raw material Substances 0.000 claims description 2
- LAJZODKXOMJMPK-UHFFFAOYSA-N tellurium dioxide Chemical compound O=[Te]=O LAJZODKXOMJMPK-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- LTSUHJWLSNQKIP-UHFFFAOYSA-J tin(iv) bromide Chemical compound Br[Sn](Br)(Br)Br LTSUHJWLSNQKIP-UHFFFAOYSA-J 0.000 claims description 2
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims description 2
- 239000010936 titanium Substances 0.000 claims description 2
- 229910052719 titanium Inorganic materials 0.000 claims description 2
- 239000004408 titanium dioxide Substances 0.000 claims description 2
- 239000011592 zinc chloride Substances 0.000 claims description 2
- 235000005074 zinc chloride Nutrition 0.000 claims description 2
- 239000011787 zinc oxide Substances 0.000 claims description 2
- 239000004593 Epoxy Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- JVTAAEKCZFNVCJ-REOHCLBHSA-N L-lactic acid Chemical compound C[C@H](O)C(O)=O JVTAAEKCZFNVCJ-REOHCLBHSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- LRWZZZWJMFNZIK-UHFFFAOYSA-N 2-chloro-3-methyloxirane Chemical compound CC1OC1Cl LRWZZZWJMFNZIK-UHFFFAOYSA-N 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- PRBHEGAFLDMLAL-GQCTYLIASA-N (4e)-hexa-1,4-diene Chemical compound C\C=C\CC=C PRBHEGAFLDMLAL-GQCTYLIASA-N 0.000 description 1
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 1
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 241001082241 Lythrum hyssopifolia Species 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000035922 thirst Effects 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
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- Polyesters Or Polycarbonates (AREA)
Abstract
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CNB2004100172127A CN1325533C (zh) | 2004-03-25 | 2004-03-25 | 一种直接熔融制备高分子量聚乳酸的方法 |
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CNB2004100172127A CN1325533C (zh) | 2004-03-25 | 2004-03-25 | 一种直接熔融制备高分子量聚乳酸的方法 |
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CN1563139A true CN1563139A (zh) | 2005-01-12 |
CN1325533C CN1325533C (zh) | 2007-07-11 |
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Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN100448910C (zh) * | 2005-07-29 | 2009-01-07 | 上海同杰良生物材料有限公司 | 聚乳酸类聚酯及其共聚物的制备新方法 |
CN100523050C (zh) * | 2007-08-02 | 2009-08-05 | 同济大学 | 一种聚乳酸-聚碳酸酯共聚物的制备方法 |
CN100558795C (zh) * | 2006-09-07 | 2009-11-11 | 同济大学 | 生物全降解聚乳酸基多元嵌段聚合物的制备方法 |
CN100558787C (zh) * | 2007-08-02 | 2009-11-11 | 同济大学 | 一种生物全降解聚酯共聚物的制备方法 |
CN101240061B (zh) * | 2008-02-22 | 2010-11-10 | 华南农业大学 | 载药用聚外消旋乳酸的合成方法 |
CN101585911B (zh) * | 2009-07-13 | 2011-08-31 | 北京化工大学 | 一釜制备支化或微交联聚乳酸的方法 |
CN101747501B (zh) * | 2008-12-12 | 2011-10-26 | 北京服装学院 | 一种高分子量聚乳酸的合成方法 |
CN103254410A (zh) * | 2013-06-03 | 2013-08-21 | 北京理工大学 | 一种基于金属粉体脱水剂的高分子量聚乳酸的制备方法 |
CN103254409A (zh) * | 2013-06-03 | 2013-08-21 | 北京理工大学 | 一种基于金属醇盐脱水剂的高分子量聚乳酸的制备方法 |
CN103254411A (zh) * | 2013-06-07 | 2013-08-21 | 北京理工大学 | 一种高分子量聚乳酸的直接缩聚扩链制备方法 |
CN114685772A (zh) * | 2022-04-20 | 2022-07-01 | 深圳光华伟业股份有限公司 | 一种新型生物医用聚乳酸合成方法 |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP3267392B2 (ja) * | 1993-06-30 | 2002-03-18 | 三井化学株式会社 | 分解性ポリマー |
CN1127532C (zh) * | 1999-12-09 | 2003-11-12 | 浙江大学 | 乳酸直接缩合聚合制备聚乳酸生物降解材料的方法 |
CN1298764C (zh) * | 2003-02-08 | 2007-02-07 | 上海同杰良生物材料有限公司 | 乳酸直接缩聚制备高分子量聚乳酸的方法 |
-
2004
- 2004-03-25 CN CNB2004100172127A patent/CN1325533C/zh not_active Expired - Fee Related
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN100448910C (zh) * | 2005-07-29 | 2009-01-07 | 上海同杰良生物材料有限公司 | 聚乳酸类聚酯及其共聚物的制备新方法 |
CN100558795C (zh) * | 2006-09-07 | 2009-11-11 | 同济大学 | 生物全降解聚乳酸基多元嵌段聚合物的制备方法 |
CN100523050C (zh) * | 2007-08-02 | 2009-08-05 | 同济大学 | 一种聚乳酸-聚碳酸酯共聚物的制备方法 |
CN100558787C (zh) * | 2007-08-02 | 2009-11-11 | 同济大学 | 一种生物全降解聚酯共聚物的制备方法 |
CN101240061B (zh) * | 2008-02-22 | 2010-11-10 | 华南农业大学 | 载药用聚外消旋乳酸的合成方法 |
CN101747501B (zh) * | 2008-12-12 | 2011-10-26 | 北京服装学院 | 一种高分子量聚乳酸的合成方法 |
CN101585911B (zh) * | 2009-07-13 | 2011-08-31 | 北京化工大学 | 一釜制备支化或微交联聚乳酸的方法 |
CN103254410A (zh) * | 2013-06-03 | 2013-08-21 | 北京理工大学 | 一种基于金属粉体脱水剂的高分子量聚乳酸的制备方法 |
CN103254409A (zh) * | 2013-06-03 | 2013-08-21 | 北京理工大学 | 一种基于金属醇盐脱水剂的高分子量聚乳酸的制备方法 |
CN103254409B (zh) * | 2013-06-03 | 2015-07-01 | 北京理工大学 | 一种基于金属醇盐脱水剂的高分子量聚乳酸的制备方法 |
CN103254411A (zh) * | 2013-06-07 | 2013-08-21 | 北京理工大学 | 一种高分子量聚乳酸的直接缩聚扩链制备方法 |
CN114685772A (zh) * | 2022-04-20 | 2022-07-01 | 深圳光华伟业股份有限公司 | 一种新型生物医用聚乳酸合成方法 |
Also Published As
Publication number | Publication date |
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CN1325533C (zh) | 2007-07-11 |
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Application publication date: 20050112 Assignee: Hangzhou Dehong Technology Co.,Ltd. Assignor: MAANSHAN TONGJIELIANG BIOLOGICAL MATERIAL CO.,LTD. Contract record no.: X2022330000058 Denomination of invention: A method for preparing high molecular weight polylactic acid by direct melting Granted publication date: 20070711 License type: Common License Record date: 20220318 |
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