CN1926126A - 从聚乳酸或其衍生物回收交酯的方法 - Google Patents
从聚乳酸或其衍生物回收交酯的方法 Download PDFInfo
- Publication number
- CN1926126A CN1926126A CNA2005800053366A CN200580005336A CN1926126A CN 1926126 A CN1926126 A CN 1926126A CN A2005800053366 A CNA2005800053366 A CN A2005800053366A CN 200580005336 A CN200580005336 A CN 200580005336A CN 1926126 A CN1926126 A CN 1926126A
- Authority
- CN
- China
- Prior art keywords
- lactic acid
- lactide
- poly
- derivatives
- aluminium hydroxide
- 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.)
- Granted
Links
- 229920000747 poly(lactic acid) Polymers 0.000 title claims abstract description 71
- JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 title claims abstract description 63
- 238000000034 method Methods 0.000 title claims abstract description 34
- 239000004626 polylactic acid Substances 0.000 title abstract description 7
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 claims abstract description 75
- 239000000203 mixture Substances 0.000 claims abstract description 46
- 230000003287 optical effect Effects 0.000 claims abstract description 22
- -1 poly(lactic acid) Polymers 0.000 claims description 156
- 229910021502 aluminium hydroxide Inorganic materials 0.000 claims description 74
- 238000000197 pyrolysis Methods 0.000 claims description 60
- 229920005989 resin Polymers 0.000 claims description 19
- 239000011347 resin Substances 0.000 claims description 19
- JJTUDXZGHPGLLC-ZXZARUISSA-N (3r,6s)-3,6-dimethyl-1,4-dioxane-2,5-dione Chemical compound C[C@H]1OC(=O)[C@H](C)OC1=O JJTUDXZGHPGLLC-ZXZARUISSA-N 0.000 claims description 13
- 238000011084 recovery Methods 0.000 claims description 9
- 150000003606 tin compounds Chemical class 0.000 claims description 9
- 239000000155 melt Substances 0.000 claims description 6
- 239000000126 substance Substances 0.000 abstract description 31
- 238000002844 melting Methods 0.000 abstract description 3
- 230000008018 melting Effects 0.000 abstract description 3
- 238000004064 recycling Methods 0.000 abstract 1
- 239000011342 resin composition Substances 0.000 abstract 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 71
- 239000004310 lactic acid Substances 0.000 description 35
- 235000014655 lactic acid Nutrition 0.000 description 35
- 229920001432 poly(L-lactide) Polymers 0.000 description 30
- JVTAAEKCZFNVCJ-REOHCLBHSA-N L-lactic acid Chemical compound C[C@H](O)C(O)=O JVTAAEKCZFNVCJ-REOHCLBHSA-N 0.000 description 29
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- 230000000052 comparative effect Effects 0.000 description 22
- 239000000463 material Substances 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 13
- 238000000354 decomposition reaction Methods 0.000 description 12
- 239000007789 gas Substances 0.000 description 11
- 238000005516 engineering process Methods 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 229910018626 Al(OH) Inorganic materials 0.000 description 8
- 239000004793 Polystyrene Substances 0.000 description 8
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 8
- 229920002223 polystyrene Polymers 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 239000003112 inhibitor Substances 0.000 description 7
- 238000001746 injection moulding Methods 0.000 description 7
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- 239000000243 solution Substances 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 6
- 238000005266 casting Methods 0.000 description 6
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- JJTUDXZGHPGLLC-IMJSIDKUSA-N 4511-42-6 Chemical compound C[C@@H]1OC(=O)[C@H](C)OC1=O JJTUDXZGHPGLLC-IMJSIDKUSA-N 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
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- 208000033962 Fontaine progeroid syndrome Diseases 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
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- 239000000654 additive Substances 0.000 description 3
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 3
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- 229910001679 gibbsite Inorganic materials 0.000 description 3
- 239000001307 helium Substances 0.000 description 3
- 229910052734 helium Inorganic materials 0.000 description 3
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
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- 238000001291 vacuum drying Methods 0.000 description 3
- JVTAAEKCZFNVCJ-UWTATZPHSA-M (R)-lactate Chemical compound C[C@@H](O)C([O-])=O JVTAAEKCZFNVCJ-UWTATZPHSA-M 0.000 description 2
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 2
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000002028 Biomass Substances 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 229910001680 bayerite Inorganic materials 0.000 description 2
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- 230000000630 rising effect Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 238000007614 solvation Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical compound O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229940032021 tetramune Drugs 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 238000012795 verification Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 150000003755 zirconium compounds Chemical class 0.000 description 1
- 229910000859 α-Fe Inorganic materials 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/12—1,4-Dioxanes; Hydrogenated 1,4-dioxanes not condensed with other rings
-
- 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
- C08J11/00—Recovery or working-up of waste materials
- C08J11/04—Recovery or working-up of waste materials of polymers
- C08J11/10—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation
- C08J11/16—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with inorganic material
-
- 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
- C08J2367/00—Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers
- C08J2367/04—Polyesters derived from hydroxy carboxylic acids, e.g. lactones
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
- Y02W30/00—Technologies for solid waste management
- Y02W30/50—Reuse, recycling or recovery technologies
- Y02W30/62—Plastics recycling; Rubber recycling
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Sustainable Development (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Separation, Recovery Or Treatment Of Waste Materials Containing Plastics (AREA)
- Polyesters Or Polycarbonates (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
PLLA/Al(OH)3PLLA/Al2O3 | 最终残渣(重量%) | 理论残渣量(重量%) | ||
重量份比 | Al化合物(重量%) | Al(OH)3→Al2O3转化率 73% | ||
比较例1 | 100/0 | 0 | ≈0 | 0 |
PLLA/Al(OH)3 | ||||
实施例1 | 100/10 | 9.1 | 7.5 | 6.6 |
实施例2 | 100/20 | 16.7 | 12.3 | 12.2 |
实施例3 | 100/30 | 23.1 | 17.8 | 16.8 |
实施例4 | 100/40 | 28.6 | 20.7 | 20.9 |
实施例5 | 100/50 | 33.3 | 24.6 | 24.3 |
实施例6 | 100/60 | 37.5 | 27.1 | 27.4 |
PLLA/Al2O3 | ||||
比较例2 | 100/10 | 9.1 | 9.7 | |
比较例3 | 100/20 | 16.7 | 16.3 | |
比较例4 | 100/30 | 23.1 | 22.6 |
热解温度范围(℃) | 分解生成物的组成(%) | |||
内消旋交酯 | L,L-/D,D-交酯 | 低聚物 | ||
实施例8 | 60-270 | 0 | 100 | 0 |
实施例9 | 60-280 | 0 | 100 | 0 |
实施例10 | 60-290 | 0 | 100 | 0 |
实施例11 | 60-300 | 0 | 100 | 0 |
实施例12 | 60-320 | 6.08 | 91.92 | 2.00 |
比较例7 | 60-340 | 7.54 | 89.00 | 3.46 |
比较例8 | 60-400 | 12.17 | 84.47 | 3.36 |
PLLA/Al(OH)3 | 最终残渣(重量%) | Al(OH)3→Al2O3转化率 (%) | ||
重量份比 | Al(OH)3(重量%) | |||
比较例9 | 100/0 | 0 | ≈0 | |
实施例14 | 100/10 | 9.1 | 8.1 | 32 |
实施例15 | 100/20 | 16.7 | 13.3 | 59 |
实施例16 | 100/30 | 23.1 | 19.0 | 51 |
PLLA/PSt/Al(OH)3 | 最终残渣(重量%) | ||
重量份比 | Al(OH)3(重量%) | ||
实施例17 | 100/100/10 | 4.8 | 4.2 |
实施例18 | 100/100/20 | 9.1 | 8.6 |
实施例19 | 100/100/30 | 13.0 | 10.5 |
Claims (6)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2004135476 | 2004-04-30 | ||
JP135476/2004 | 2004-04-30 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1926126A true CN1926126A (zh) | 2007-03-07 |
CN100475808C CN100475808C (zh) | 2009-04-08 |
Family
ID=35241610
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNB2005800053366A Expired - Fee Related CN100475808C (zh) | 2004-04-30 | 2005-04-25 | 从聚乳酸或其衍生物回收交酯的方法 |
Country Status (6)
Country | Link |
---|---|
US (1) | US7557224B2 (zh) |
EP (1) | EP1741707A4 (zh) |
JP (1) | JP4517069B2 (zh) |
KR (1) | KR100830022B1 (zh) |
CN (1) | CN100475808C (zh) |
WO (1) | WO2005105775A1 (zh) |
Cited By (2)
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CN102348673A (zh) * | 2009-04-14 | 2012-02-08 | 银河股份公司 | 水解法化学回收聚乳酸 |
CN103210043A (zh) * | 2010-10-05 | 2013-07-17 | 东洋制罐株式会社 | 生物降解性树脂组合物 |
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JP5193475B2 (ja) * | 2007-02-16 | 2013-05-08 | 帝人株式会社 | ポリ乳酸からラクチドを製造する方法 |
JP2009058856A (ja) * | 2007-09-03 | 2009-03-19 | Canon Inc | 画像形成装置 |
JP2009249508A (ja) * | 2008-04-07 | 2009-10-29 | Kyushu Institute Of Technology | ポリ乳酸製品の効率的オリゴマー化方法 |
JP4986244B2 (ja) * | 2008-11-22 | 2012-07-25 | 公益財団法人北九州産業学術推進機構 | 難燃化乳酸ポリマー組成物からのラクチドの回収方法 |
JP5051729B2 (ja) * | 2009-01-20 | 2012-10-17 | 公益財団法人北九州産業学術推進機構 | ラクチドの回収装置および回収方法 |
JP5376373B2 (ja) * | 2010-02-10 | 2013-12-25 | 公益財団法人北九州産業学術推進機構 | ラクチドの回収方法 |
JP5286505B2 (ja) * | 2011-01-19 | 2013-09-11 | 東洋製罐株式会社 | 生分解性樹脂組成物 |
WO2014000277A1 (zh) * | 2012-06-29 | 2014-01-03 | 孝感市易生新材料有限公司 | 一种利用回收的聚乳酸制备丙交酯的方法 |
EP2725019B1 (de) | 2012-10-26 | 2015-04-08 | Uhde Inventa-Fischer GmbH | Verfahren zur Herstellung cyclischer Diester, insbesondere Dilactid |
WO2014086840A1 (de) | 2012-12-04 | 2014-06-12 | Uhde Inventa-Fischer Gmbh | Verfahren zur selektiven chemischen extraktion von milchsäure aus polymerblends |
US9284414B2 (en) | 2013-11-26 | 2016-03-15 | Globalfoundries Inc. | Flame retardant polymers containing renewable content |
US9346922B2 (en) | 2013-11-26 | 2016-05-24 | International Business Machines Corporation | Flame retardant block copolymers from renewable feeds |
CN104861157B (zh) * | 2015-06-01 | 2016-09-28 | 中国科学院长春应用化学研究所 | 一种低光学纯度高分子量聚乳酸的制备方法 |
EP3793973B1 (de) | 2018-05-18 | 2022-12-28 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Verfahren zur herstellung eines intramolekularen diesters einer hydroxycarbonsäure sowie verfahren zur herstellung einer polyhydroxycarbonsäure |
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JPH06279434A (ja) * | 1993-03-24 | 1994-10-04 | Dainippon Ink & Chem Inc | ラクタイド類の製造方法 |
DE4325849A1 (de) * | 1993-07-31 | 1995-02-02 | Basf Ag | Flammwidrig ausgerüstetes Polylactid und Copolylactid |
JP3518931B2 (ja) * | 1995-06-15 | 2004-04-12 | 松下電器産業株式会社 | 熱硬化性組成物、モールド材、およびモールド材成形体の分解処理方法 |
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JPH10306091A (ja) * | 1997-05-08 | 1998-11-17 | Shimadzu Corp | ラクチドの製造方法 |
JP2000015107A (ja) * | 1998-06-29 | 2000-01-18 | Shimadzu Corp | ラクチド化触媒及びラクチド製造方法 |
US6864351B2 (en) * | 2000-09-14 | 2005-03-08 | Daicel Chemical Industries, Inc. | Aliphatic copolyester resin, a preparation method, an aliphatic polyester resin composition, uses thereof, a coating composition, a particle-state composition for agriculture and gardening coated by degradable layer |
JP2001303387A (ja) | 2000-04-26 | 2001-10-31 | Kyowa Co Ltd | 生分解性を有する建設工事用シート |
JP4445181B2 (ja) * | 2001-10-15 | 2010-04-07 | ソニー株式会社 | 生分解性を有する難燃性複合組成物およびその製造方法 |
JP2003192925A (ja) | 2001-10-15 | 2003-07-09 | Sony Corp | 生分解性を有する難燃性複合組成物およびその製造方法 |
JP3980446B2 (ja) | 2002-08-13 | 2007-09-26 | 富士通株式会社 | 生分解性樹脂組成物、並びに、生分解性樹脂組成物用充填材及び成形体 |
-
2005
- 2005-04-25 CN CNB2005800053366A patent/CN100475808C/zh not_active Expired - Fee Related
- 2005-04-25 WO PCT/JP2005/007813 patent/WO2005105775A1/ja not_active Application Discontinuation
- 2005-04-25 KR KR20067021525A patent/KR100830022B1/ko not_active IP Right Cessation
- 2005-04-25 US US11/579,144 patent/US7557224B2/en not_active Expired - Fee Related
- 2005-04-25 EP EP05734554A patent/EP1741707A4/en not_active Withdrawn
- 2005-04-25 JP JP2006512774A patent/JP4517069B2/ja not_active Expired - Fee Related
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
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CN102348673A (zh) * | 2009-04-14 | 2012-02-08 | 银河股份公司 | 水解法化学回收聚乳酸 |
CN102348673B (zh) * | 2009-04-14 | 2015-04-15 | 银河股份公司 | 水解法化学回收聚乳酸 |
CN103210043A (zh) * | 2010-10-05 | 2013-07-17 | 东洋制罐株式会社 | 生物降解性树脂组合物 |
Also Published As
Publication number | Publication date |
---|---|
WO2005105775A1 (ja) | 2005-11-10 |
KR20070009625A (ko) | 2007-01-18 |
US20080004454A1 (en) | 2008-01-03 |
EP1741707A4 (en) | 2009-02-25 |
JP4517069B2 (ja) | 2010-08-04 |
CN100475808C (zh) | 2009-04-08 |
JPWO2005105775A1 (ja) | 2008-03-13 |
KR100830022B1 (ko) | 2008-05-15 |
US7557224B2 (en) | 2009-07-07 |
EP1741707A1 (en) | 2007-01-10 |
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