JP6347083B2 - ポリエステル樹脂ベースのバイオプラスチックを安定化させるための方法 - Google Patents
ポリエステル樹脂ベースのバイオプラスチックを安定化させるための方法 Download PDFInfo
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- JP6347083B2 JP6347083B2 JP2017501681A JP2017501681A JP6347083B2 JP 6347083 B2 JP6347083 B2 JP 6347083B2 JP 2017501681 A JP2017501681 A JP 2017501681A JP 2017501681 A JP2017501681 A JP 2017501681A JP 6347083 B2 JP6347083 B2 JP 6347083B2
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- Prior art keywords
- carbodiimide
- formula
- polyester resin
- bio
- 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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- 238000000034 method Methods 0.000 title claims description 21
- 239000004645 polyester resin Substances 0.000 title claims description 18
- 229920001225 polyester resin Polymers 0.000 title claims description 12
- 230000000087 stabilizing effect Effects 0.000 title claims description 5
- 229920000704 biodegradable plastic Polymers 0.000 title description 2
- 150000001718 carbodiimides Chemical class 0.000 claims description 29
- 229920003023 plastic Polymers 0.000 claims description 22
- 239000004033 plastic Substances 0.000 claims description 22
- 239000004626 polylactic acid Substances 0.000 claims description 14
- -1 polybutylene adipate terephthalate Polymers 0.000 claims description 10
- 230000007062 hydrolysis Effects 0.000 claims description 8
- 238000006460 hydrolysis reaction Methods 0.000 claims description 8
- 238000000855 fermentation Methods 0.000 claims description 6
- 230000004151 fermentation Effects 0.000 claims description 6
- 239000004629 polybutylene adipate terephthalate Substances 0.000 claims description 6
- 229920002961 polybutylene succinate Polymers 0.000 claims description 6
- 239000004631 polybutylene succinate Substances 0.000 claims description 6
- 239000005014 poly(hydroxyalkanoate) Substances 0.000 claims description 4
- 229920000642 polymer Polymers 0.000 claims description 4
- 235000000346 sugar Nutrition 0.000 claims description 4
- 229920002472 Starch Polymers 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 3
- 235000014633 carbohydrates Nutrition 0.000 claims description 3
- 150000001720 carbohydrates Chemical class 0.000 claims description 3
- 150000002009 diols Chemical class 0.000 claims description 3
- 238000010348 incorporation Methods 0.000 claims description 3
- 239000000178 monomer Substances 0.000 claims description 3
- 230000000379 polymerizing effect Effects 0.000 claims description 3
- 235000019698 starch Nutrition 0.000 claims description 3
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 3
- 239000008158 vegetable oil Substances 0.000 claims description 3
- 239000004609 Impact Modifier Substances 0.000 claims description 2
- 239000012963 UV stabilizer Substances 0.000 claims description 2
- 239000003607 modifier Substances 0.000 claims description 2
- 239000002667 nucleating agent Substances 0.000 claims description 2
- 239000012783 reinforcing fiber Substances 0.000 claims description 2
- 239000008107 starch Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 229920005989 resin Polymers 0.000 claims 1
- 239000011347 resin Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 8
- 229920003232 aliphatic polyester Polymers 0.000 description 6
- 229920000747 poly(lactic acid) Polymers 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- JVTAAEKCZFNVCJ-REOHCLBHSA-N L-lactic acid Chemical compound C[C@H](O)C(O)=O JVTAAEKCZFNVCJ-REOHCLBHSA-N 0.000 description 4
- 239000003925 fat Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 229930182843 D-Lactic acid Natural products 0.000 description 2
- JVTAAEKCZFNVCJ-UWTATZPHSA-N D-lactic acid Chemical compound C[C@@H](O)C(O)=O JVTAAEKCZFNVCJ-UWTATZPHSA-N 0.000 description 2
- ZBVOEVQTNYNNMY-UHFFFAOYSA-N O=P1=CCCC1 Chemical class O=P1=CCCC1 ZBVOEVQTNYNNMY-UHFFFAOYSA-N 0.000 description 2
- 229920001222 biopolymer Polymers 0.000 description 2
- 229940022769 d- lactic acid Drugs 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 229920001707 polybutylene terephthalate Polymers 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 2
- 150000008163 sugars Chemical class 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- 229920001736 Metabolix Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000003819 basic metal compounds Chemical class 0.000 description 1
- 229920000229 biodegradable polyester Polymers 0.000 description 1
- 239000004622 biodegradable polyester Substances 0.000 description 1
- 230000000035 biogenic effect Effects 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- GWLJTAJEHRYMCA-UHFFFAOYSA-N phospholane Chemical class C1CCPC1 GWLJTAJEHRYMCA-UHFFFAOYSA-N 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 238000012643 polycondensation polymerization Methods 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000903 polyhydroxyalkanoate Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000013501 sustainable material Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/797—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing carbodiimide and/or uretone-imine groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/29—Compounds containing one or more carbon-to-nitrogen double bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4266—Polycondensates having carboxylic or carbonic ester groups in the main chain prepared from hydroxycarboxylic acids and/or lactones
- C08G18/4283—Hydroxycarboxylic acid or ester
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0016—Plasticisers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/04—Polyesters derived from hydroxycarboxylic acids, e.g. lactones
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Biological Depolymerization Polymers (AREA)
Description
のカルボジイミドを、プラスチックの中に組み入れる。
のカルボジイミドおよび/または式(II)
CDI I:本発明実施例のための、式(II)のカルボジイミド
CDI II:比較例のための、ビス−2,6−ジイソプロピルフェニルカルボジイミド
CDI III:比較例のための、トリイソプロピルフェニルジイソシアネートをベースとするポリマー性カルボジイミド
市場で入手可能なポリ乳酸(PLA)3251D(NatureWorks LLC製)
それぞれのカルボジイミドは、ZSK 25実験室用二軸スクリューエクストルーダー(Werner & Pfleiderer製)の手段により温度190℃でポリ乳酸の中に組み入れた。
Claims (9)
- 0.5〜2.0重量%、極めて特に好ましくは1〜1.5重量%の、前記式(I)または(II)のカルボジイミドが使用されることを特徴とする、請求項1または2に記載のプロセス。
- 前記ポリエステル樹脂をベースとするバイオベースのプラスチックが、発酵によって得られるモノマーまたはデンプンから、糖から、炭水化物から、脂肪から、もしくは植物油から発酵によって得られるポリマーを重合させることによって製造される脂肪族ポリエステル樹脂であるか、または、バイオジェニック的に製造されたジオール成分をベースとする脂肪族−芳香族ポリエステル樹脂であるか、またはその酸成分が天然由来の物質から得られるバイオポリアミドであることを特徴とする、請求項1〜3のいずれか一項に記載のプロセス。
- 前記バイオベースのポリエステル樹脂が、ポリ乳酸(PLA)、ポリヒドロキシアルカノエート(PHA)、ポリブチレンアジペートテレフタレート(PBAT)、ポリブチレンスクシネート(PBS)、および/またはポリブチレンスクシネートテレフタレート(PBST)、好ましくはポリ乳酸(PLA)であることを特徴とする、請求項4に記載のプロセス。
- 前記組み入れが、エクストルーダーによって達成されることを特徴とする、請求項1〜5のいずれか一項に記載のプロセス。
- 前記組み入れが、150〜280℃の温度で達成されることを特徴とする、請求項1〜6のいずれか一項に記載のプロセス。
- 成核剤、補強繊維、耐衝撃性改良剤、流動性改良剤、および/またはUV安定剤がさらなる添加剤として使用されることを特徴とする、請求項1〜7のいずれか一項に記載のプロセス。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP14176949.7A EP2975083B1 (de) | 2014-07-14 | 2014-07-14 | Verfahren zur Stabilisierung von biobasiertem Kunststoff auf Basis von Polyesterharz |
EP14176949.7 | 2014-07-14 | ||
PCT/EP2015/065967 WO2016008843A1 (de) | 2014-07-14 | 2015-07-13 | Verfahren zur stabilisierung von biobasiertem kunststoff auf basis von polyester-harz |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2017520665A JP2017520665A (ja) | 2017-07-27 |
JP6347083B2 true JP6347083B2 (ja) | 2018-06-27 |
Family
ID=51167806
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2017501681A Active JP6347083B2 (ja) | 2014-07-14 | 2015-07-13 | ポリエステル樹脂ベースのバイオプラスチックを安定化させるための方法 |
Country Status (9)
Country | Link |
---|---|
US (1) | US10494505B2 (ja) |
EP (1) | EP2975083B1 (ja) |
JP (1) | JP6347083B2 (ja) |
KR (1) | KR102507432B1 (ja) |
CN (1) | CN106661187B (ja) |
ES (1) | ES2622379T3 (ja) |
PL (1) | PL2975083T3 (ja) |
PT (1) | PT2975083T (ja) |
WO (1) | WO2016008843A1 (ja) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113698720A (zh) * | 2021-08-09 | 2021-11-26 | 华合新材料科技股份有限公司 | 一种高抗菌、可生物降解的pmma合金材料及其制备方法 |
Family Cites Families (23)
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DE1130594B (de) | 1956-07-30 | 1962-05-30 | Du Pont | Verfahren zur Herstellung von gegebenenfalls modifizierten Polykondensationsprodukten mití¬N?C?N-Brueckengliedern |
US2840589A (en) * | 1957-06-14 | 1958-06-24 | Du Pont | Di(3-isocyanato-4-methylphenyl) carbodiimide |
DE1156401B (de) | 1960-05-24 | 1963-10-31 | Bayer Ag | Verfahren zur Herstellung von Carbodiimiden |
DE3438563A1 (de) * | 1984-10-20 | 1986-04-24 | Bayer Ag, 5090 Leverkusen | Waessrige loesungen oder dispersionen von polyisocyanat-additionsprodukten, ein verfahren zu ihrer herstellung, sowie ihre verwendung als beschichtungsmittel oder als leimungsmittel fuer papier |
US5973024A (en) | 1997-07-09 | 1999-10-26 | Nisshinbo Industries, Inc. | Method for control of biodegradation rate of biodegradable plastic |
DE10106630A1 (de) * | 2001-02-12 | 2002-08-22 | Jowat Lobers U Frank Gmbh & Co | Selbsttragendes reaktives Schmelzklebeelement und seine Verwendung |
DE10146328A1 (de) * | 2001-09-20 | 2003-04-10 | Basf Ag | Hydrolysestabilisierte Formmassen |
DE10210956B4 (de) * | 2002-02-19 | 2008-03-13 | Jowat Ag | Reaktives Einkomponenten-Beschichtungs- und/oder -Klebstoffgranulat und Verfahren zu seiner Herstellung sowie seine Verwendung |
JP4084953B2 (ja) | 2002-04-18 | 2008-04-30 | 日清紡績株式会社 | 生分解性プラスチック組成物とその成形品及び生分解速度制御方法 |
EP1627894A4 (en) | 2003-05-20 | 2006-05-24 | Mitsubishi Plastics Inc | REFLECTIVE RESIN FILM BASED ON ALIPHATIC POLYESTER AND REFLECTIVE PLATE |
JP4585749B2 (ja) * | 2003-08-07 | 2010-11-24 | 日清紡ホールディングス株式会社 | 黄変を抑えたカルボジイミド組成物、耐加水分解安定剤及び熱可塑性樹脂組成物 |
JP2005082642A (ja) | 2003-09-05 | 2005-03-31 | Nisshinbo Ind Inc | エステル基を有する樹脂用の耐加水分解安定剤及び熱可塑性樹脂組成物 |
JP4643154B2 (ja) * | 2004-02-17 | 2011-03-02 | ユニチカ株式会社 | 熱可塑性樹脂組成物、およびそれを成形してなる成形体。 |
TWI397553B (zh) | 2005-04-26 | 2013-06-01 | Unitika Ltd | 生物分解性樹脂組成物、由該組成物構成之成形體,及該組成物之製造方法 |
EP2418247A1 (de) * | 2010-08-11 | 2012-02-15 | Rhein Chemie Rheinau GmbH | Langlebige biobasierte Kunststoffe, ein Verfahren zu deren Herstellung und deren Verwendung |
EP2418250A1 (de) * | 2010-08-11 | 2012-02-15 | Rhein Chemie Rheinau GmbH | Langlebige biobasierte Kunststoffe auf Basis von Polyhydroxyalkanoat, ein Verfahren zu deren Herstellung und deren Verwendung |
EP2423185B1 (de) * | 2010-08-30 | 2017-03-01 | Rhein Chemie Rheinau GmbH | Neuartige wässrige resorcin-formaldehyd-latex-dispersionen, haftungsverbesserte fasern, verfahren zu deren herstellung und deren verwendung |
EP2423186B1 (de) * | 2010-08-30 | 2017-05-31 | LANXESS Deutschland GmbH | Neuartige haftvermittler auf basis von carbodiimiden, haftvermittlerhaltige, wässrige resorcin-formaldehyd-latex-dispersionen, haftungsverbesserte fasern, verfahren zu deren herstellung und deren verwendung |
CA2754313A1 (en) * | 2010-10-13 | 2012-04-13 | Rhein Chemie Rheinau Gmbh | New dispersion adhesives, a process for preparing them and use thereof |
CN103517941A (zh) * | 2011-05-06 | 2014-01-15 | 莱茵化学莱瑙有限公司 | 新颖的基于多羟基烷酸酯(pha)的持久水解稳定的生物基塑料、其生产方法及其用途 |
JP5922499B2 (ja) * | 2012-05-31 | 2016-05-24 | 三洋化成工業株式会社 | 樹脂改質剤 |
CN103897356B (zh) * | 2012-12-27 | 2016-03-09 | 中纺投资发展股份有限公司 | 一种耐水解耐高温的热塑性聚酯弹性体组合物 |
CN103865245A (zh) * | 2014-03-18 | 2014-06-18 | 杭州曦茂新材料科技有限公司 | 一种抗水解聚乳酸树脂的制备方法 |
-
2014
- 2014-07-14 PT PT141769497T patent/PT2975083T/pt unknown
- 2014-07-14 ES ES14176949.7T patent/ES2622379T3/es active Active
- 2014-07-14 PL PL14176949T patent/PL2975083T3/pl unknown
- 2014-07-14 EP EP14176949.7A patent/EP2975083B1/de active Active
-
2015
- 2015-07-13 CN CN201580038223.XA patent/CN106661187B/zh active Active
- 2015-07-13 KR KR1020177004000A patent/KR102507432B1/ko active IP Right Grant
- 2015-07-13 WO PCT/EP2015/065967 patent/WO2016008843A1/de active Application Filing
- 2015-07-13 JP JP2017501681A patent/JP6347083B2/ja active Active
- 2015-07-13 US US15/325,141 patent/US10494505B2/en active Active
Also Published As
Publication number | Publication date |
---|---|
KR102507432B1 (ko) | 2023-03-07 |
EP2975083B1 (de) | 2017-01-25 |
PT2975083T (pt) | 2017-04-24 |
ES2622379T3 (es) | 2017-07-06 |
US10494505B2 (en) | 2019-12-03 |
US20170190873A1 (en) | 2017-07-06 |
JP2017520665A (ja) | 2017-07-27 |
WO2016008843A1 (de) | 2016-01-21 |
KR20170030626A (ko) | 2017-03-17 |
CN106661187A (zh) | 2017-05-10 |
PL2975083T3 (pl) | 2017-07-31 |
CN106661187B (zh) | 2019-11-05 |
EP2975083A1 (de) | 2016-01-20 |
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