CA2859547A1 - 2,5-furan dicarboxylic acid-based polyesters prepared from biomass - Google Patents
2,5-furan dicarboxylic acid-based polyesters prepared from biomass Download PDFInfo
- Publication number
- CA2859547A1 CA2859547A1 CA2859547A CA2859547A CA2859547A1 CA 2859547 A1 CA2859547 A1 CA 2859547A1 CA 2859547 A CA2859547 A CA 2859547A CA 2859547 A CA2859547 A CA 2859547A CA 2859547 A1 CA2859547 A1 CA 2859547A1
- Authority
- CA
- Canada
- Prior art keywords
- shows
- diol
- copolyester
- isosorbide
- temperature
- 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
- CHTHALBTIRVDBM-UHFFFAOYSA-N furan-2,5-dicarboxylic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)O1 CHTHALBTIRVDBM-UHFFFAOYSA-N 0.000 title claims abstract description 61
- 229920000728 polyester Polymers 0.000 title claims abstract description 35
- 239000002028 Biomass Substances 0.000 title abstract description 14
- KLDXJTOLSGUMSJ-JGWLITMVSA-N Isosorbide Chemical compound O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 KLDXJTOLSGUMSJ-JGWLITMVSA-N 0.000 claims abstract description 39
- 229960002479 isosorbide Drugs 0.000 claims abstract description 38
- 239000000178 monomer Substances 0.000 claims abstract description 31
- 229920001634 Copolyester Polymers 0.000 claims abstract description 27
- -1 polyethylene Polymers 0.000 claims abstract description 27
- 150000002009 diols Chemical class 0.000 claims abstract description 18
- 150000002148 esters Chemical class 0.000 claims abstract description 16
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims abstract description 13
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 8
- 125000005907 alkyl ester group Chemical group 0.000 claims abstract description 8
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 claims abstract description 6
- 239000004698 Polyethylene Substances 0.000 claims abstract description 5
- DNXDYHALMANNEJ-UHFFFAOYSA-N furan-2,3-dicarboxylic acid Chemical compound OC(=O)C=1C=COC=1C(O)=O DNXDYHALMANNEJ-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229920000573 polyethylene Polymers 0.000 claims abstract description 5
- 238000010438 heat treatment Methods 0.000 claims description 41
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 40
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 38
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 22
- 229910052757 nitrogen Inorganic materials 0.000 claims description 20
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical group O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 claims description 19
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 18
- 239000011541 reaction mixture Substances 0.000 claims description 15
- 239000003054 catalyst Substances 0.000 claims description 12
- 235000013361 beverage Nutrition 0.000 claims description 5
- 235000013305 food Nutrition 0.000 claims description 5
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 2
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 2
- 239000004411 aluminium Substances 0.000 claims description 2
- 229910052782 aluminium Inorganic materials 0.000 claims description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 2
- 229910017052 cobalt Inorganic materials 0.000 claims description 2
- 239000010941 cobalt Substances 0.000 claims description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000010703 silicon Substances 0.000 claims description 2
- 229910052710 silicon Inorganic materials 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 239000010936 titanium Substances 0.000 claims description 2
- 229910052719 titanium Inorganic materials 0.000 claims description 2
- 229910052726 zirconium Inorganic materials 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 229920000139 polyethylene terephthalate Polymers 0.000 abstract description 6
- 239000005020 polyethylene terephthalate Substances 0.000 abstract description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
- 229920000642 polymer Polymers 0.000 description 66
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 60
- 238000000113 differential scanning calorimetry Methods 0.000 description 47
- 239000000203 mixture Substances 0.000 description 34
- 239000002904 solvent Substances 0.000 description 32
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 25
- 230000000875 corresponding effect Effects 0.000 description 23
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 21
- 238000005481 NMR spectroscopy Methods 0.000 description 21
- 238000001228 spectrum Methods 0.000 description 20
- YQUVCSBJEUQKSH-UHFFFAOYSA-N protochatechuic acid Natural products OC(=O)C1=CC=C(O)C(O)=C1 YQUVCSBJEUQKSH-UHFFFAOYSA-N 0.000 description 19
- WKOLLVMJNQIZCI-UHFFFAOYSA-N vanillic acid Chemical compound COC1=CC(C(O)=O)=CC=C1O WKOLLVMJNQIZCI-UHFFFAOYSA-N 0.000 description 19
- TUUBOHWZSQXCSW-UHFFFAOYSA-N vanillic acid Natural products COC1=CC(O)=CC(C(O)=O)=C1 TUUBOHWZSQXCSW-UHFFFAOYSA-N 0.000 description 19
- 230000015572 biosynthetic process Effects 0.000 description 17
- 238000006068 polycondensation reaction Methods 0.000 description 17
- 239000002253 acid Substances 0.000 description 15
- 238000003786 synthesis reaction Methods 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- DSLRVRBSNLHVBH-UHFFFAOYSA-N 2,5-furandimethanol Chemical compound OCC1=CC=C(CO)O1 DSLRVRBSNLHVBH-UHFFFAOYSA-N 0.000 description 13
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 13
- DTQVDTLACAAQTR-DYCDLGHISA-N trifluoroacetic acid-d1 Chemical compound [2H]OC(=O)C(F)(F)F DTQVDTLACAAQTR-DYCDLGHISA-N 0.000 description 12
- 238000002441 X-ray diffraction Methods 0.000 description 11
- 238000001816 cooling Methods 0.000 description 11
- 229920005610 lignin Polymers 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 8
- 238000005086 pumping Methods 0.000 description 8
- NSQYDLCQAQCMGE-UHFFFAOYSA-N 2-butyl-4-hydroxy-5-methylfuran-3-one Chemical compound CCCCC1OC(C)=C(O)C1=O NSQYDLCQAQCMGE-UHFFFAOYSA-N 0.000 description 7
- 238000002425 crystallisation Methods 0.000 description 7
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 230000008025 crystallization Effects 0.000 description 6
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 238000004090 dissolution Methods 0.000 description 5
- 230000010354 integration Effects 0.000 description 5
- NOEGNKMFWQHSLB-UHFFFAOYSA-N 5-hydroxymethylfurfural Chemical compound OCC1=CC=C(C=O)O1 NOEGNKMFWQHSLB-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 230000015556 catabolic process Effects 0.000 description 4
- 238000006731 degradation reaction Methods 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 238000001157 Fourier transform infrared spectrum Methods 0.000 description 3
- 239000001361 adipic acid Substances 0.000 description 3
- 235000011037 adipic acid Nutrition 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 150000002402 hexoses Chemical class 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- 238000002411 thermogravimetry Methods 0.000 description 3
- 239000002023 wood Substances 0.000 description 3
- GSNUFIFRDBKVIE-UHFFFAOYSA-N 2,5-dimethylfuran Chemical compound CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 2
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 229920006125 amorphous polymer Polymers 0.000 description 2
- 238000005452 bending Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 125000001142 dicarboxylic acid group Chemical group 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 239000012634 fragment Substances 0.000 description 2
- 150000004676 glycans Chemical class 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920001282 polysaccharide Polymers 0.000 description 2
- 239000005017 polysaccharide Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- 150000008163 sugars Chemical class 0.000 description 2
- ZWVMLYRJXORSEP-LURJTMIESA-N (2s)-hexane-1,2,6-triol Chemical compound OCCCC[C@H](O)CO ZWVMLYRJXORSEP-LURJTMIESA-N 0.000 description 1
- OFBQJSOFQDEBGM-QDNHWIQGSA-N 1,5-dideuteriopentane Chemical compound C(CCCC[2H])[2H] OFBQJSOFQDEBGM-QDNHWIQGSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- YQPCHPBGAALCRT-UHFFFAOYSA-N 2-[1-(carboxymethyl)cyclohexyl]acetic acid Chemical compound OC(=O)CC1(CC(O)=O)CCCCC1 YQPCHPBGAALCRT-UHFFFAOYSA-N 0.000 description 1
- UHVMKWLQGQBLFM-UHFFFAOYSA-N 3,8,13-trioxabicyclo[8.2.1]trideca-1(12),10-diene-2,9-dione Chemical compound O=C1OCCCCOC(=O)C2=CC=C1O2 UHVMKWLQGQBLFM-UHFFFAOYSA-N 0.000 description 1
- RBQLGIKHSXQZTB-UHFFFAOYSA-N 3-methylpentane-2,4-diol Chemical compound CC(O)C(C)C(C)O RBQLGIKHSXQZTB-UHFFFAOYSA-N 0.000 description 1
- MHNMEERHZSPWFL-NSOVKSMOSA-N 4-[(1s)-1-amino-1-(3-methylimidazol-4-yl)ethyl]-2-[3-[(3s)-3-ethyl-1-methyl-2-oxoazepan-3-yl]phenoxy]benzonitrile Chemical compound C=1C=CC(OC=2C(=CC=C(C=2)[C@](C)(N)C=2N(C=NC=2)C)C#N)=CC=1[C@]1(CC)CCCCN(C)C1=O MHNMEERHZSPWFL-NSOVKSMOSA-N 0.000 description 1
- OCKGFTQIICXDQW-ZEQRLZLVSA-N 5-[(1r)-1-hydroxy-2-[4-[(2r)-2-hydroxy-2-(4-methyl-1-oxo-3h-2-benzofuran-5-yl)ethyl]piperazin-1-yl]ethyl]-4-methyl-3h-2-benzofuran-1-one Chemical compound C1=C2C(=O)OCC2=C(C)C([C@@H](O)CN2CCN(CC2)C[C@H](O)C2=CC=C3C(=O)OCC3=C2C)=C1 OCKGFTQIICXDQW-ZEQRLZLVSA-N 0.000 description 1
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- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
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- 101100301581 Mus musculus Retnla gene Proteins 0.000 description 1
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- 229920001059 synthetic polymer Polymers 0.000 description 1
- 238000003856 thermoforming Methods 0.000 description 1
- 238000001757 thermogravimetry curve 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
- C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
- C08G63/181—Acids containing aromatic rings
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B1/00—Layered products having a non-planar shape
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
- C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
- C08G63/181—Acids containing aromatic rings
- C08G63/183—Terephthalic acids
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/66—Polyesters containing oxygen in the form of ether groups
- C08G63/668—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/672—Dicarboxylic acids and dihydroxy compounds
-
- 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
- Y10T428/13—Hollow or container type article [e.g., tube, vase, etc.]
- Y10T428/1352—Polymer or resin containing [i.e., natural or synthetic]
- Y10T428/1397—Single layer [continuous layer]
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Polyesters Or Polycarbonates (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Packages (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Wrappers (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261582983P | 2012-01-04 | 2012-01-04 | |
| US61/582,983 | 2012-01-04 | ||
| PCT/US2012/071766 WO2013103574A1 (en) | 2012-01-04 | 2012-12-27 | 2,5-furan dicarboxylic acid-based polyesters prepared from biomass |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2859547A1 true CA2859547A1 (en) | 2013-07-11 |
Family
ID=47501551
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2859547A Abandoned CA2859547A1 (en) | 2012-01-04 | 2012-12-27 | 2,5-furan dicarboxylic acid-based polyesters prepared from biomass |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US20130171397A1 (enExample) |
| EP (1) | EP2800771A1 (enExample) |
| JP (1) | JP2015507684A (enExample) |
| CN (1) | CN104379631A (enExample) |
| AU (1) | AU2012363608B2 (enExample) |
| BR (1) | BR112014016453A8 (enExample) |
| CA (1) | CA2859547A1 (enExample) |
| IN (1) | IN2014MN01416A (enExample) |
| MX (1) | MX2014008097A (enExample) |
| RU (1) | RU2606515C2 (enExample) |
| WO (1) | WO2013103574A1 (enExample) |
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| WO2012054742A2 (en) | 2010-10-20 | 2012-04-26 | BIOS2 Medical, Inc. | Implantable polymer for bone and vascular lesions |
| US11291483B2 (en) | 2010-10-20 | 2022-04-05 | 206 Ortho, Inc. | Method and apparatus for treating bone fractures, and/or for fortifying and/or augmenting bone, including the provision and use of composite implants |
| US11058796B2 (en) | 2010-10-20 | 2021-07-13 | 206 Ortho, Inc. | Method and apparatus for treating bone fractures, and/or for fortifying and/or augmenting bone, including the provision and use of composite implants, and novel composite structures which may be used for medical and non-medical applications |
| WO2015095745A1 (en) | 2010-10-20 | 2015-06-25 | 206 Ortho, Inc. | Method and apparatus for treating bone fractures, and/or for fortifying and/or augmenting bone, including the provision and use of composite implants, and novel composite structures which may be used for medical and non-medical applications |
| US11484627B2 (en) | 2010-10-20 | 2022-11-01 | 206 Ortho, Inc. | Method and apparatus for treating bone fractures, and/or for fortifying and/or augmenting bone, including the provision and use of composite implants, and novel composite structures which may be used for medical and non-medical applications |
| WO2014190289A2 (en) | 2013-05-23 | 2014-11-27 | 206 Ortho, Inc. | Method and apparatus for treating bone fractures, and/or for fortifying and/or augmenting bone, including the provision and use of composite implants |
| US10525169B2 (en) | 2010-10-20 | 2020-01-07 | 206 Ortho, Inc. | Method and apparatus for treating bone fractures, and/or for fortifying and/or augmenting bone, including the provision and use of composite implants, and novel composite structures which may be used for medical and non-medical applications |
| EP2819620A4 (en) | 2012-02-29 | 2015-11-04 | 206 Ortho Inc | METHOD AND APPARATUS FOR TREATING BONE FRACTURES, INCLUDING THE USE OF COMPOSITE IMPLANTS |
| US9725558B2 (en) * | 2013-03-15 | 2017-08-08 | Sulzer Chemtech Ag | Process to prepare a cyclic oligomer and a cyclic oligomer obtainable thereby |
| WO2014139602A1 (en) * | 2013-03-15 | 2014-09-18 | Sulzer Chemtech Ag | A process to prepare a polyester polymer composition comprising a polyester polymer having furanic units and a polyester polymer composition obtainable thereby and the use thereof |
| DE102013223496A1 (de) * | 2013-11-18 | 2015-05-21 | Tesa Se | Neuartiges Polyester geeignet zur Herstellung von Trägermaterialien für Klebebändern |
| KR101586412B1 (ko) * | 2014-01-28 | 2016-01-18 | 한국기술교육대학교 산학협력단 | 공중합 폴리에스터와 폴리락트산을 포함하는 수지 블렌드 및 그 제조방법 |
| TR201807609T4 (tr) * | 2014-03-11 | 2018-06-21 | Synvina C V | Bir poliesterin özel esterleştirme şartlarında hazırlanması için usul. |
| TR201811203T4 (tr) | 2014-03-11 | 2018-08-27 | Synvina C V | Polyester ve böyle bir polyesteri hazırlamaya yönelik usul. |
| US10316140B2 (en) | 2014-03-21 | 2019-06-11 | Furanix Technologies B.V. | Polyesters comprising 2,5-furandicarboxylate and saturated diol units having a high glass transition temperature |
| MX380350B (es) * | 2014-04-30 | 2025-03-12 | Stichting Wageningen Res | Poliesteres y copoliesteres termoplasticos de furanoato de poliisoidida y un uso de los mismos en envasado de llenado en caliente. |
| EP3154444B1 (en) | 2014-05-08 | 2022-02-23 | 206 Ortho, Inc. | Method and apparatus for treating bone fractures, and/or for fortifying and/or augmenting bone, including the provision and use of composite implants, and novel composite structures which may be used for medical and non-medical applications |
| AU2014411407B2 (en) | 2014-11-12 | 2020-06-18 | Renmatix, Inc. | Method of coalescing a substance |
| US9321714B1 (en) | 2014-12-05 | 2016-04-26 | Uop Llc | Processes and catalysts for conversion of 2,5-dimethylfuran derivatives to terephthalate |
| WO2017049239A1 (en) * | 2015-09-17 | 2017-03-23 | Micromidas, Inc. | Polymers and methods of producing thereof |
| WO2017091435A1 (en) * | 2015-11-24 | 2017-06-01 | Archer Daniels Midland Company | Oligomerizations of fdca and glycols in a one-pot esterification-transesterification process catalyzed by homogeneous organometallic lewis acids |
| CN108473666A (zh) | 2015-12-11 | 2018-08-31 | 埃维昂矿泉水有限公司 | 具有可为生物来源的抗结晶共聚单体的pet聚合物 |
| EP3402787A4 (en) | 2016-01-13 | 2019-11-27 | Stora Enso Oyj | PROCESS FOR THE PREPARATION OF 2,5-FURANDIC ACETIC ACID AND INTERMEDIATES AND DERIVATIVES THEREOF |
| US11111057B2 (en) * | 2016-03-04 | 2021-09-07 | Amisha Patel | Bioplastic collapsible dispensing tube |
| ITUA20162764A1 (it) * | 2016-04-20 | 2017-10-20 | Novamont Spa | Nuovo poliestere e composizioni che lo contengono |
| CN109476857B (zh) | 2016-07-15 | 2022-07-29 | 株式会社可乐丽 | 密封剂膜和其制备方法 |
| CN109906245A (zh) | 2016-09-16 | 2019-06-18 | 微麦德斯公司 | 聚合物及产生其的方法 |
| CA3039502A1 (en) | 2016-10-05 | 2018-04-12 | Furanix Technologies B.V. | Process for the production of a solid-state polymerized poly(tetramethylene-2,5-furan dicarboxylate) polymer and polymer thus produced |
| US10155907B2 (en) | 2016-12-12 | 2018-12-18 | International Business Machines Corporation | Cross-linkable flame retardant materials |
| US10106564B2 (en) | 2016-12-12 | 2018-10-23 | International Business Machines Corporation | Furan-containing flame retardant molecules |
| US9822208B1 (en) | 2017-01-03 | 2017-11-21 | International Business Machines Corporation | Flame retardant materials derived from furan dicarboxylic methyl ester |
| CA3051600A1 (en) | 2017-01-26 | 2018-08-02 | Synvina C.V. | 2,5-furandicarboxylic acid-based polyesters |
| SG11201913469PA (en) | 2017-07-12 | 2020-01-30 | Stora Enso Oyj | Purified 2,5-furandicarboxylic acid pathway products |
| WO2019060403A1 (en) * | 2017-09-19 | 2019-03-28 | Swimc Llc | COATING COMPOSITIONS COMPRISING A FURANE-CONTAINING POLYESTER, ARTICLES AND METHODS OF COATING APPLICATION |
| EP3476912B1 (de) | 2017-10-25 | 2022-08-17 | Henkel AG & Co. KGaA | Klebstoffe basierend auf polyesterpolyolen auf basis von aus nachwachsenden rohstoffen gewonnener furandicarbonsäure |
| KR102052935B1 (ko) * | 2018-02-14 | 2019-12-06 | 한국화학연구원 | 폴리헤테로아릴렌에테르 공중합체 및 이의 제조방법 |
| WO2019214575A1 (zh) * | 2018-05-10 | 2019-11-14 | 中国科学院长春应用化学研究所 | 一种新型呋喃生物基聚醚酯共聚物及其制备方法 |
| JP7374168B2 (ja) * | 2018-07-12 | 2023-11-06 | フラニックス・テクノロジーズ・ベーフェー | 容器の製造方法及びその容器 |
| US12246879B2 (en) | 2018-08-12 | 2025-03-11 | Amisha Patel | Environmentally friendly can |
| US11434037B2 (en) * | 2018-08-12 | 2022-09-06 | Amisha Patel | Furan can |
| CN109575257B (zh) * | 2018-11-16 | 2021-09-07 | 中国科学院宁波材料技术与工程研究所 | 聚2,5-呋喃二甲酸-1,4-丁二酸新戊二醇酯及其制备方法、制品 |
| CN110183633B (zh) * | 2019-04-15 | 2021-03-16 | 中国科学院化学研究所 | 1,4；3,6-二缩水己六醇改性的呋喃二甲酸基无规共聚物及其制法与应用 |
| CN110229480B (zh) * | 2019-07-10 | 2021-09-10 | 中国科学院宁波材料技术与工程研究所 | 一种聚呋喃二甲酸丁二醇酯和聚对苯二甲酸丁二醇酯共混物的制备方法 |
| CN110862524B (zh) * | 2019-11-28 | 2021-04-02 | 东华大学 | 一种生物基高透明度高分子薄膜及其制备方法 |
| CN110903469B (zh) * | 2019-11-28 | 2021-04-02 | 东华大学 | 一种低结晶性生物可降解聚酯及其制备方法 |
| TWI868275B (zh) * | 2019-12-20 | 2025-01-01 | 日商東洋紡股份有限公司 | 雙軸配向聚酯膜及其製造方法 |
| CN113493561A (zh) * | 2020-03-20 | 2021-10-12 | 中国科学院大连化学物理研究所 | 一种2,6-萘二甲酸基共聚酯材料及其制备方法 |
| AU2021263427A1 (en) * | 2020-04-30 | 2022-11-10 | Covation Inc. | Light-weight hot-fill container and methods for making the same |
| ES2924086T3 (es) * | 2020-05-15 | 2022-10-04 | Archer Daniels Midland Co | Producción conjunta de monómeros, incluyendo al menos un monómero de base biológica |
| JP2022144048A (ja) * | 2021-03-18 | 2022-10-03 | 三菱ケミカル株式会社 | ポリエステル樹脂およびそれを用いた成形品 |
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| US2600376A (en) * | 1949-11-26 | 1952-06-17 | Eastman Kodak Co | Polmesters of hydroxybenzoic acids |
| JPH06238747A (ja) * | 1993-02-22 | 1994-08-30 | Toray Ind Inc | ポリエステルフィルム |
| US6352426B1 (en) * | 1998-03-19 | 2002-03-05 | Advanced Plastics Technologies, Ltd. | Mold for injection molding multilayer preforms |
| US5959066A (en) * | 1998-04-23 | 1999-09-28 | Hna Holdings, Inc. | Polyesters including isosorbide as a comonomer and methods for making same |
| US6063464A (en) * | 1998-04-23 | 2000-05-16 | Hna Holdings, Inc. | Isosorbide containing polyesters and methods for making same |
| US6063465A (en) * | 1998-04-23 | 2000-05-16 | Hna Holdings, Inc. | Polyester container and method for making same |
| US6914120B2 (en) * | 2002-11-13 | 2005-07-05 | Eastman Chemical Company | Method for making isosorbide containing polyesters |
| RU2312871C2 (ru) * | 2003-08-12 | 2007-12-20 | Мицуи Кемикалз, Инк. | Смола на основе сложного полиэфира и формованный продукт из ламината на основе смолы из сложного полиэфира |
| JP4881127B2 (ja) * | 2005-11-07 | 2012-02-22 | キヤノン株式会社 | 高分子化合物およびその合成方法 |
| JP5446121B2 (ja) * | 2007-04-24 | 2014-03-19 | 三菱化学株式会社 | フラン構造を含むポリエステル |
| US20090018264A1 (en) * | 2007-07-12 | 2009-01-15 | Canon Kabushiki Kaisha | Resin composition |
| JP5371259B2 (ja) * | 2008-02-20 | 2013-12-18 | キヤノン株式会社 | ポリエステル樹脂、その製造方法、成形品用組成物及び成形品 |
| NL2002382C2 (en) * | 2008-12-30 | 2010-07-01 | Furanix Technologies Bv | A process for preparing a polymer having a 2,5-furandicarboxylate moiety within the polymer backbone and such (co)polymers. |
| CN102190782B (zh) * | 2010-03-17 | 2015-08-19 | 东丽纤维研究所（中国）有限公司 | 一种共聚酯化合物以及制备方法 |
| CN101899145B (zh) * | 2010-07-28 | 2012-07-11 | 江南大学 | 一种2,5-呋喃二甲酸基聚酯的制备方法 |
| CN102276812B (zh) * | 2011-06-29 | 2012-11-21 | 中国科学院长春应用化学研究所 | 一种聚2,5-呋喃二甲酸二醇酯的制备方法 |
| CN102432847B (zh) * | 2011-08-25 | 2013-10-16 | 中国科学院长春应用化学研究所 | 2,5-呋喃二甲酸-对苯二甲酸-脂肪族二元醇共聚酯及其制备方法 |
-
2012
- 2012-12-27 IN IN1416MUN2014 patent/IN2014MN01416A/en unknown
- 2012-12-27 RU RU2014132068A patent/RU2606515C2/ru active
- 2012-12-27 JP JP2014551279A patent/JP2015507684A/ja active Pending
- 2012-12-27 BR BR112014016453A patent/BR112014016453A8/pt not_active Application Discontinuation
- 2012-12-27 CA CA2859547A patent/CA2859547A1/en not_active Abandoned
- 2012-12-27 AU AU2012363608A patent/AU2012363608B2/en active Active
- 2012-12-27 WO PCT/US2012/071766 patent/WO2013103574A1/en not_active Ceased
- 2012-12-27 CN CN201280066195.9A patent/CN104379631A/zh active Pending
- 2012-12-27 MX MX2014008097A patent/MX2014008097A/es unknown
- 2012-12-27 US US13/728,286 patent/US20130171397A1/en not_active Abandoned
- 2012-12-27 EP EP12810023.7A patent/EP2800771A1/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| BR112014016453A2 (pt) | 2017-06-13 |
| AU2012363608A1 (en) | 2014-07-03 |
| RU2014132068A (ru) | 2016-02-27 |
| BR112014016453A8 (pt) | 2017-07-04 |
| JP2015507684A (ja) | 2015-03-12 |
| US20130171397A1 (en) | 2013-07-04 |
| WO2013103574A1 (en) | 2013-07-11 |
| CN104379631A (zh) | 2015-02-25 |
| RU2606515C2 (ru) | 2017-01-10 |
| AU2012363608B2 (en) | 2015-09-24 |
| IN2014MN01416A (enExample) | 2015-04-03 |
| EP2800771A1 (en) | 2014-11-12 |
| MX2014008097A (es) | 2015-04-13 |
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Legal Events
| Date | Code | Title | Description |
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| EEER | Examination request |
Effective date: 20140616 |
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| FZDE | Discontinued |
Effective date: 20171106 |