JP4517069B2 - ポリ乳酸又はその誘導体からラクチドを回収する方法 - Google Patents
ポリ乳酸又はその誘導体からラクチドを回収する方法 Download PDFInfo
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- JP4517069B2 JP4517069B2 JP2006512774A JP2006512774A JP4517069B2 JP 4517069 B2 JP4517069 B2 JP 4517069B2 JP 2006512774 A JP2006512774 A JP 2006512774A JP 2006512774 A JP2006512774 A JP 2006512774A JP 4517069 B2 JP4517069 B2 JP 4517069B2
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- Japan
- Prior art keywords
- lactide
- polylactic acid
- derivative
- aluminum hydroxide
- weight
- 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 description 66
- 239000004626 polylactic acid Substances 0.000 title claims description 66
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- 238000000034 method Methods 0.000 title claims description 38
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 claims description 74
- 238000005979 thermal decomposition reaction Methods 0.000 claims description 36
- 239000000203 mixture Substances 0.000 claims description 34
- 230000003287 optical effect Effects 0.000 claims description 29
- 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 14
- 239000011342 resin composition Substances 0.000 claims description 12
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- 238000002844 melting Methods 0.000 claims description 7
- 230000008018 melting Effects 0.000 claims description 7
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 67
- 229920000642 polymer Polymers 0.000 description 38
- 239000004310 lactic acid Substances 0.000 description 33
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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 22
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- 230000000052 comparative effect Effects 0.000 description 14
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- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 12
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- 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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- JVTAAEKCZFNVCJ-UWTATZPHSA-N D-lactic acid Chemical compound C[C@@H](O)C(O)=O JVTAAEKCZFNVCJ-UWTATZPHSA-N 0.000 description 2
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
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- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
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- 229910052782 aluminium Inorganic materials 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
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- 239000003505 polymerization initiator Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920001955 polyphenylene ether Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- XOJVVFBFDXDTEG-UHFFFAOYSA-N pristane Chemical compound CC(C)CCCC(C)CCCC(C)CCCC(C)C XOJVVFBFDXDTEG-UHFFFAOYSA-N 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000013585 weight reducing agent Substances 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
Description
塩酸処理によって金属を殆ど含まないポリ(L−乳酸)(PLLA)(Mn=279000、Mw/Mn=1.90、スズ含有量=17ppm)200mgと、表1に示した量の水酸化アルミニウム、又は比較例としてのアルミナをサンプル管にとり、これにクロロホルム5mLを加えて、室温下12時間、激しく磁気攪拌を行うことによって水酸化アルミニウム又はアルミナが均一に分散したPLLA溶液を調整した。次に、この溶液からフラットシャーレ中でキャストフィルムを作成した。得られたキャストフィルムは、メタノールで表面を洗浄した後、室温で1日真空乾燥を行った。得られたフィルムから、一回につき約5mgのサンプルを切り出し、SEIKO製TG/DTA6200を用いて、窒素雰囲気下、室温から400℃までの温度範囲で、5℃/分の昇温速度で熱分解を行った。その結果を図1と表1に示した。
実施例3で作成した精製PLLA/水酸化アルミニウム(100/30重量比)のフィルムを用いて、熱分解ガスクロマトグラフ−マススペクトル(Py−GC/MS)分析を行った。サンプラー付き熱分解装置(フロンティアラボ社製PY2020D、島津製作所製GC-17A + GCMS-QP5050)に、不活性ガス(ヘリウム)を通しながら,60℃に予熱した熱分解オーブンの中に、フィルムサンプル10μgをすばやく投入した。その後、10℃/分で300℃まで昇温した。60〜300℃の温度範囲での熱分解生成物は、サンプラーを用いて分取され、GC/MSを用いて分析された。分析の結果、全生成物中のラクチドの割合は、99.52%であり、メソ−ラクチドの含有率は0.56%であった。ラクチド以外の生成物としては、環状4量体および5量体の保持時間とほぼ同じ場所に、それぞれ0.28および0.20%のピークが観察されたのみであった。
実施例3で作成した精製PLLA/水酸化アルミニウム(100/30重量比)のフィルムを用いて、熱分解ガスクロマトグラフ−マススペクトル(Py−GC/MS)分析を行った。サンプラー付き熱分解装置(フロンティアラボ社製PY2020D、島津製作所製GC-17A + GCMS-QP5050)に、不活性ガス(ヘリウム)を通しながら,60℃に予熱した熱分解オーブンの中に、フィルムサンプル10μgをすばやく投入した。その後、10℃/分で表2に示した温度まで昇温した。所定の温度範囲での熱分解生成物は、サンプラーを用いて分取され、GC/MSを用いて分析された。分析の結果は表2に示した。その結果、60−300℃の温度範囲では(実施例8〜11)、メソ−ラクチドおよび環状オリゴマーの生成は全く観測されず、ほぼ純粋なL,L−ラクチドが得られることが確認された。60−320℃では(実施例12)、メソ−ラクチドおよび環状オリゴマーの生成が若干観測され、それぞれ、6.08および2.00%であった。さらに、高温域ではメソ−ラクチドおよび環状オリゴマーの生成が増大した(比較例7〜8)。
実施例3で作成した精製PLLA/水酸化アルミニウム(100/30重量比)のフィルム150mgを、柴田製熱分解用ガラスチューブオーブンGTO-350D中に入れ、真空/窒素ガス置換を3回行った。その後、窒素雰囲気下でガラスチューブオーブンの温度を280℃まで徐々に上昇し、その後、その温度で2時間保持した。室温トラップに回収された熱分解生成物は、光学分割用キャピラリーカラム Varian cyclodextrine-β-236M-19(0.25 mm × 50 m)を備えた、島津製作所製ガスクロマトグラフGC-9Aを用いて分析した。その結果、生成物の組成は、L,L-ラクチド95.30%、メソ−ラクチド4.19%。D,D-ラクチド0.51%であった。
オクタン酸スズを触媒として合成したPLLA(Mn=150000、Mw/Mn=2.48、スズ含有量=388ppm)200mgと、表3に示した量の水酸化アルミニウムをサンプル管にとり、これにクロロホルム5mLを加えて、室温下12時間、激しく磁気攪拌を行うことによって、水酸化アルミニウムが均一分散したPLLA溶液を調整した。次にこの溶液からフラットシャーレ中で、キャストフィルムを作成した。得られたキャストフィルムは、メタノールで表面を洗浄した後、室温で1日真空乾燥を行った。得られたフィルムから、一回につき約5mgのサンプルを切り出し、SEIKO製TG/DTA6200を用いて、窒素雰囲気下、室温から400℃までの温度範囲で、1℃/分の昇温速度で熱分解を行った。その結果を図2と表3に示した。
オクタン酸スズを触媒として合成したPLLA(Mn=150000、Mw/Mn=2.48、スズ含有量=388ppm)100mgとポリスチレン(PSt)(Scientific Polymer Products, Inc.社製、Mw=280000)100mgに、表4に示した量の水酸化アルミニウムをサンプル管にとり、これにクロロホルム5mLを加えて、室温下12時間、激しく磁気攪拌を行うことによって、水酸化アルミニウムが均一分散したPLLA/PSt溶液を調整した。次に、この溶液からフラットシャーレ中でキャストフィルムを作成した。得られたキャストフィルムは、メタノールで表面を洗浄した後、室温で1日真空乾燥を行った。得られたフィルムから、一回につき約5mgのサンプルを切り出し、SEIKO製TG/DTA6200を用いて、窒素雰囲気下、室温から500℃までの温度範囲で、9℃/分の昇温速度で熱分解を行った。その結果を図3に示した。
Claims (6)
- ポリ乳酸又はその誘導体と水酸化アルミニウムとの混合物を、ポリ乳酸又はその誘導体の溶融温度以上で320℃以下の温度範囲において熱分解しラクチドを回収することを特徴とする、ポリ乳酸又はその誘導体からラクチドを回収する方法。
- 混合物が、ポリ乳酸又はその誘導体と水酸化アルミニウムを含む樹脂組成物からなるものである、請求項1記載のポリ乳酸又はその誘導体からラクチドを回収する方法。
- 混合物が、ポリ乳酸又はその誘導体100重量部に対して水酸化アルミニウム10〜100重量部からなるものである、請求項1又は2記載のポリ乳酸又はその誘導体からラクチドを回収する方法。
- ポリ乳酸又はその誘導体が、スズ化合物を含有するものである、請求項1〜3いずれか1つに記載のポリ乳酸又はその誘導体からラクチドを回収する方法。
- 熱分解温度が200〜300℃の温度範囲である、請求項1〜4いずれか1つに記載のポリ乳酸又はその誘導体からラクチドを回収する方法。
- ポリ乳酸又はその誘導体の光学純度が80%e.e.以上であって、且つ得られるラクチド中のメソラクチドの含有率が10モル%以下である、請求項1〜5いずれか1つに記載のポリ乳酸又はその誘導体からラクチドを回収する方法。
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PCT/JP2005/007813 WO2005105775A1 (ja) | 2004-04-30 | 2005-04-25 | ポリ乳酸又はその誘導体からラクチドを回収する方法 |
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US (1) | US7557224B2 (ja) |
EP (1) | EP1741707A4 (ja) |
JP (1) | JP4517069B2 (ja) |
KR (1) | KR100830022B1 (ja) |
CN (1) | CN100475808C (ja) |
WO (1) | WO2005105775A1 (ja) |
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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 |
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 |
ES2536294T3 (es) | 2012-10-26 | 2015-05-22 | Uhde Inventa-Fischer Gmbh | Procedimiento para preparar diésteres cíclicos, especialmente dilactida |
WO2014086840A1 (de) | 2012-12-04 | 2014-06-12 | 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 |
BE1028899B1 (nl) | 2020-12-15 | 2022-07-19 | Despriet Gebroeders Nv | Systeem voor de recyclage van polymelkzuur in afvalstromen om lactide te verkrijgen |
BE1028893B1 (nl) | 2020-12-15 | 2022-07-19 | Despriet Gebroeders Nv | Recyclageproces voor polymelkzuur in afvalstromen om lactide te verkrijgen |
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- 2005-04-25 JP JP2006512774A patent/JP4517069B2/ja not_active Expired - Fee Related
- 2005-04-25 CN CNB2005800053366A patent/CN100475808C/zh not_active Expired - Fee Related
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CN1926126A (zh) | 2007-03-07 |
US7557224B2 (en) | 2009-07-07 |
JPWO2005105775A1 (ja) | 2008-03-13 |
KR100830022B1 (ko) | 2008-05-15 |
US20080004454A1 (en) | 2008-01-03 |
KR20070009625A (ko) | 2007-01-18 |
EP1741707A4 (en) | 2009-02-25 |
EP1741707A1 (en) | 2007-01-10 |
WO2005105775A1 (ja) | 2005-11-10 |
CN100475808C (zh) | 2009-04-08 |
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