CA2712709A1 - Process for the plasticization of lactic acid polymers - Google Patents
Process for the plasticization of lactic acid polymers Download PDFInfo
- Publication number
- CA2712709A1 CA2712709A1 CA2712709A CA2712709A CA2712709A1 CA 2712709 A1 CA2712709 A1 CA 2712709A1 CA 2712709 A CA2712709 A CA 2712709A CA 2712709 A CA2712709 A CA 2712709A CA 2712709 A1 CA2712709 A1 CA 2712709A1
- Authority
- CA
- Canada
- Prior art keywords
- lactic acid
- mixture
- oligomers
- phase
- acid polymers
- 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.)
- Abandoned
Links
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 title claims abstract description 88
- 239000004310 lactic acid Substances 0.000 title claims abstract description 44
- 235000014655 lactic acid Nutrition 0.000 title claims abstract description 44
- 229920000642 polymer Polymers 0.000 title claims abstract description 25
- 238000000034 method Methods 0.000 title claims abstract description 18
- 230000008569 process Effects 0.000 title claims description 16
- 239000000203 mixture Substances 0.000 claims abstract description 36
- 238000002156 mixing Methods 0.000 claims abstract description 6
- 239000007787 solid Substances 0.000 claims abstract description 6
- 238000000227 grinding Methods 0.000 claims abstract description 4
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 230000032050 esterification Effects 0.000 claims description 9
- 238000005886 esterification reaction Methods 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000000524 functional group Chemical group 0.000 claims description 5
- 238000001125 extrusion Methods 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 150000005846 sugar alcohols Polymers 0.000 claims 2
- 238000003490 calendering Methods 0.000 claims 1
- 238000002347 injection Methods 0.000 claims 1
- 239000007924 injection Substances 0.000 claims 1
- 238000000465 moulding Methods 0.000 claims 1
- 230000000977 initiatory effect Effects 0.000 abstract 1
- 238000007493 shaping process Methods 0.000 abstract 1
- 229920000747 poly(lactic acid) Polymers 0.000 description 22
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 239000010408 film Substances 0.000 description 13
- 238000004821 distillation Methods 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 9
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 6
- 229920006381 polylactic acid film Polymers 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 230000035484 reaction time Effects 0.000 description 6
- 239000001117 sulphuric acid Substances 0.000 description 6
- 235000011149 sulphuric acid Nutrition 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 4
- 239000004698 Polyethylene Substances 0.000 description 4
- 238000013019 agitation Methods 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 239000004014 plasticizer Substances 0.000 description 4
- -1 poly(vinyl chloride) Polymers 0.000 description 4
- 229920000915 polyvinyl chloride Polymers 0.000 description 4
- 239000004800 polyvinyl chloride Substances 0.000 description 4
- 239000012429 reaction media Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 208000034530 PLAA-associated neurodevelopmental disease Diseases 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 238000003475 lamination Methods 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920005670 poly(ethylene-vinyl chloride) Polymers 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 239000005968 1-Decanol Substances 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- KVZLHPXEUGJPAH-UHFFFAOYSA-N 2-oxidanylpropanoic acid Chemical compound CC(O)C(O)=O.CC(O)C(O)=O KVZLHPXEUGJPAH-UHFFFAOYSA-N 0.000 description 1
- 241000193830 Bacillus <bacterium> Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229920006125 amorphous polymer Polymers 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 239000002440 industrial waste Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000003754 machining Methods 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 235000013379 molasses Nutrition 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229920006126 semicrystalline polymer Polymers 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 239000005418 vegetable material Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- 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
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/18—Plasticising macromolecular compounds
-
- 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
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyesters Or Polycarbonates (AREA)
- Biological Depolymerization Polymers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/ES2008/000038 WO2009092825A1 (es) | 2008-01-25 | 2008-01-25 | Procedimiento de plastificación de polímeros de ácido láctico |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2712709A1 true CA2712709A1 (en) | 2009-07-30 |
Family
ID=40900782
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2712709A Abandoned CA2712709A1 (en) | 2008-01-25 | 2008-01-25 | Process for the plasticization of lactic acid polymers |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US8084551B2 (enExample) |
| EP (1) | EP2256149B1 (enExample) |
| JP (1) | JP5598673B2 (enExample) |
| CN (1) | CN101970547A (enExample) |
| CA (1) | CA2712709A1 (enExample) |
| ES (1) | ES2602578T3 (enExample) |
| WO (1) | WO2009092825A1 (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2017142551A (ru) | 2015-05-07 | 2019-06-07 | Новас Интернэшнл, Инк. | Модификаторы пластмасс |
| WO2017168398A1 (en) * | 2016-03-31 | 2017-10-05 | Dandelion Research Limited | Polylactic acid moulding process |
| US10584306B2 (en) | 2017-08-11 | 2020-03-10 | Board Of Regents Of The University Of Oklahoma | Surfactant microemulsions |
| FR3083543B1 (fr) | 2018-07-06 | 2021-03-05 | Carbiolice | Matiere plastique à haute teneur en pla comprenant un ester de citrate |
| FR3083544B1 (fr) | 2018-07-06 | 2020-09-11 | Carbiolice | Matiere plastique à haute teneur en pla comprenant des oligomeres d’acide lactique |
| FR3094268B1 (fr) | 2019-03-28 | 2021-03-19 | Carbiolice | Article multicouche enzymé |
| FR3098519B1 (fr) | 2019-07-10 | 2021-07-23 | Carbiolice | Matiere plastique à haute teneur en pla comprenant du ppgdge |
| FR3106592B1 (fr) | 2020-01-24 | 2022-08-05 | Carbiolice | Procédé de Préparation d’un Mélange Maître Enzymé |
| FR3106591B1 (fr) | 2020-01-24 | 2022-08-05 | Carbiolice | Utilisation d’un melange enzyme pour ameliorer les proprietes mecaniques d’un article comprenant le melange enzyme et un polymere biodegradable |
| FR3125533B1 (fr) | 2021-07-20 | 2024-11-01 | Carbiolice | Procédé de Préparation d’un Mélange Maître Enzymé |
| FR3139500B1 (fr) | 2022-09-14 | 2024-09-27 | Carbiolice | ARTICLE MULTICOUCHE ENZYMÉ ayant des propriétés barrières à l’eau |
| FR3139569A1 (fr) | 2022-09-14 | 2024-03-15 | Carbiolice | ARTICLE MONOCOUCHE ENZYMÉ ayant des propriétés barrières à l’eau |
| FR3144996A1 (fr) | 2023-01-18 | 2024-07-19 | Carbiolice | Melange maitre enzyme comprenant des proteines |
| WO2025190969A1 (fr) | 2024-03-12 | 2025-09-18 | Carbiolice | Article méthanisable enzymé |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5424346A (en) * | 1988-08-08 | 1995-06-13 | Ecopol, Llc | Biodegradable replacement of crystal polystyrene |
| US5502158A (en) * | 1988-08-08 | 1996-03-26 | Ecopol, Llc | Degradable polymer composition |
| CA1339026C (en) * | 1988-08-08 | 1997-03-25 | Richard G. Sinclair | Degradable thermoplastics from lactides |
| ES2017562A6 (es) * | 1988-08-08 | 1991-02-16 | Batelle Memorial Insitute | Composiciones biodegradables en el medio ambiente y procedimiento para su obtencion. |
| US5180765A (en) * | 1988-08-08 | 1993-01-19 | Biopak Technology, Ltd. | Biodegradable packaging thermoplastics from lactides |
| AU8660191A (en) * | 1990-09-06 | 1992-03-30 | Biopak Technology, Ltd. | Packaging thermoplastics from lactic acid |
| KR100209818B1 (ko) * | 1992-09-04 | 1999-07-15 | 사또 아끼오 | 분해성점착필름 및 분해성수지조성물 |
| JP3290496B2 (ja) | 1993-04-21 | 2002-06-10 | 三井化学株式会社 | 熱可塑性ポリマー組成物 |
| JP3399130B2 (ja) * | 1995-01-27 | 2003-04-21 | 株式会社島津製作所 | 可塑化されたポリ乳酸及びその成型品 |
| JP4336991B2 (ja) * | 2003-01-30 | 2009-09-30 | 荒川化学工業株式会社 | 樹脂用可塑剤及び樹脂組成物 |
| JP2006152102A (ja) * | 2004-11-29 | 2006-06-15 | Arakawa Chem Ind Co Ltd | 乳酸系樹脂組成物、当該組成物を用いて得られる成形品及びフィルム |
-
2008
- 2008-01-25 CN CN200880125622.XA patent/CN101970547A/zh active Pending
- 2008-01-25 JP JP2010543529A patent/JP5598673B2/ja not_active Expired - Fee Related
- 2008-01-25 ES ES08718439.6T patent/ES2602578T3/es active Active
- 2008-01-25 WO PCT/ES2008/000038 patent/WO2009092825A1/es not_active Ceased
- 2008-01-25 CA CA2712709A patent/CA2712709A1/en not_active Abandoned
- 2008-01-25 EP EP08718439.6A patent/EP2256149B1/en not_active Not-in-force
- 2008-01-25 US US12/864,093 patent/US8084551B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US8084551B2 (en) | 2011-12-27 |
| JP2011510148A (ja) | 2011-03-31 |
| WO2009092825A1 (es) | 2009-07-30 |
| ES2602578T3 (es) | 2017-02-21 |
| JP5598673B2 (ja) | 2014-10-01 |
| US20110054099A1 (en) | 2011-03-03 |
| CN101970547A (zh) | 2011-02-09 |
| EP2256149A1 (en) | 2010-12-01 |
| EP2256149B1 (en) | 2016-08-10 |
| EP2256149A4 (en) | 2012-03-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20130125 |
|
| FZDE | Discontinued |
Effective date: 20160121 |