CN100475808C - 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
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- CN100475808C CN100475808C CNB2005800053366A CN200580005336A CN100475808C CN 100475808 C CN100475808 C CN 100475808C CN B2005800053366 A CNB2005800053366 A CN B2005800053366A CN 200580005336 A CN200580005336 A CN 200580005336A CN 100475808 C CN100475808 C CN 100475808C
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- 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.)
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- 229920000747 poly(lactic acid) Polymers 0.000 title claims abstract description 77
- JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 title claims abstract description 68
- 238000000034 method Methods 0.000 title claims abstract description 38
- 239000004626 polylactic acid Substances 0.000 title abstract description 6
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 claims abstract description 76
- 239000000203 mixture Substances 0.000 claims abstract description 46
- 230000003287 optical effect Effects 0.000 claims abstract description 23
- -1 poly(lactic acid) Polymers 0.000 claims description 170
- 229910021502 aluminium hydroxide Inorganic materials 0.000 claims description 75
- 238000000197 pyrolysis Methods 0.000 claims description 60
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- 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 12
- 150000003606 tin compounds Chemical class 0.000 claims description 10
- 239000000155 melt Substances 0.000 claims description 6
- 239000000126 substance Substances 0.000 abstract description 30
- 238000002844 melting Methods 0.000 abstract description 3
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- 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
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- JVTAAEKCZFNVCJ-REOHCLBHSA-N L-lactic acid Chemical compound C[C@H](O)C(O)=O JVTAAEKCZFNVCJ-REOHCLBHSA-N 0.000 description 23
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- 230000000052 comparative effect Effects 0.000 description 15
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- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 13
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- 238000000354 decomposition reaction Methods 0.000 description 11
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
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- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 6
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- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 3
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- 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
- 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
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- 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
Images
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Abstract
Description
Claims (10)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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JP2004135476 | 2004-04-30 | ||
JP135476/2004 | 2004-04-30 |
Publications (2)
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CN1926126A CN1926126A (zh) | 2007-03-07 |
CN100475808C true CN100475808C (zh) | 2009-04-08 |
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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 |
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US (1) | US7557224B2 (zh) |
EP (1) | EP1741707A4 (zh) |
JP (1) | JP4517069B2 (zh) |
KR (1) | KR100830022B1 (zh) |
CN (1) | CN100475808C (zh) |
WO (1) | WO2005105775A1 (zh) |
Families Citing this family (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
BE1018716A3 (fr) * | 2009-04-14 | 2011-07-05 | Galactic Sa | Recyclage chimique du pla par hydrolyse. |
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 |
JP5829393B2 (ja) * | 2010-10-05 | 2015-12-09 | 東洋製罐株式会社 | 生分解性樹脂組成物 |
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 |
EP2928948A1 (de) | 2012-12-04 | 2015-10-14 | Uhde Inventa-Fischer GmbH | Verfahren zur selektiven chemischen extraktion von milchsäure aus polymerblends |
US9346922B2 (en) | 2013-11-26 | 2016-05-24 | International Business Machines Corporation | Flame retardant block copolymers from renewable feeds |
US9284414B2 (en) | 2013-11-26 | 2016-03-15 | Globalfoundries Inc. | Flame retardant polymers containing renewable content |
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 |
CN111285840A (zh) * | 2020-03-04 | 2020-06-16 | 东北林业大学 | 一种通过共热解从废弃聚乳酸中提取丙交酯的方法 |
BE1028893B1 (nl) | 2020-12-15 | 2022-07-19 | Despriet Gebroeders Nv | Recyclageproces voor polymelkzuur in afvalstromen om lactide te verkrijgen |
BE1028899B1 (nl) | 2020-12-15 | 2022-07-19 | Despriet Gebroeders Nv | Systeem voor de recyclage van polymelkzuur in afvalstromen om lactide te verkrijgen |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
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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 |
JPH1036553A (ja) * | 1996-07-26 | 1998-02-10 | Shimadzu Corp | 脂肪族ポリエステル廃棄物の処理方法 |
JP4075089B2 (ja) * | 1996-12-09 | 2008-04-16 | トヨタ自動車株式会社 | ラクチドの製造方法 |
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 |
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 |
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 |
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 KR KR20067021525A patent/KR100830022B1/ko not_active IP Right Cessation
- 2005-04-25 WO PCT/JP2005/007813 patent/WO2005105775A1/ja not_active Application Discontinuation
- 2005-04-25 US US11/579,144 patent/US7557224B2/en not_active Expired - Fee Related
- 2005-04-25 JP JP2006512774A patent/JP4517069B2/ja not_active Expired - Fee Related
- 2005-04-25 EP EP05734554A patent/EP1741707A4/en not_active Withdrawn
- 2005-04-25 CN CNB2005800053366A patent/CN100475808C/zh not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
JPWO2005105775A1 (ja) | 2008-03-13 |
JP4517069B2 (ja) | 2010-08-04 |
KR100830022B1 (ko) | 2008-05-15 |
CN1926126A (zh) | 2007-03-07 |
EP1741707A1 (en) | 2007-01-10 |
US20080004454A1 (en) | 2008-01-03 |
KR20070009625A (ko) | 2007-01-18 |
EP1741707A4 (en) | 2009-02-25 |
WO2005105775A1 (ja) | 2005-11-10 |
US7557224B2 (en) | 2009-07-07 |
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