CA2587345C - High performance p(vdf-trfe) copolymer for pyroelectric conversion - Google Patents
High performance p(vdf-trfe) copolymer for pyroelectric conversion Download PDFInfo
- Publication number
- CA2587345C CA2587345C CA2587345A CA2587345A CA2587345C CA 2587345 C CA2587345 C CA 2587345C CA 2587345 A CA2587345 A CA 2587345A CA 2587345 A CA2587345 A CA 2587345A CA 2587345 C CA2587345 C CA 2587345C
- Authority
- CA
- Canada
- Prior art keywords
- copolymer
- trfe
- vdf
- purified
- solution
- 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.)
- Expired - Fee Related
Links
- 229920001577 copolymer Polymers 0.000 title claims abstract description 59
- 238000006243 chemical reaction Methods 0.000 title abstract description 19
- 229920001166 Poly(vinylidene fluoride-co-trifluoroethylene) Polymers 0.000 claims abstract description 28
- 238000000034 method Methods 0.000 claims abstract description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 20
- 230000008569 process Effects 0.000 claims abstract description 15
- 239000002904 solvent Substances 0.000 claims abstract description 11
- 239000002244 precipitate Substances 0.000 claims abstract description 10
- 239000008188 pellet Substances 0.000 claims abstract description 8
- 238000001556 precipitation Methods 0.000 claims abstract description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical group CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 30
- 238000007605 air drying Methods 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims 3
- 238000001035 drying Methods 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 230000007704 transition Effects 0.000 abstract description 21
- 239000012535 impurity Substances 0.000 abstract description 7
- 239000012071 phase Substances 0.000 description 17
- 239000000463 material Substances 0.000 description 16
- 230000010287 polarization Effects 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 230000005684 electric field Effects 0.000 description 8
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 7
- 230000007423 decrease Effects 0.000 description 7
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- 230000005611 electricity Effects 0.000 description 5
- 239000013014 purified material Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 239000002109 single walled nanotube Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 239000002033 PVDF binder Substances 0.000 description 3
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- 238000000638 solvent extraction Methods 0.000 description 3
- MIZLGWKEZAPEFJ-UHFFFAOYSA-N 1,1,2-trifluoroethene Chemical group FC=C(F)F MIZLGWKEZAPEFJ-UHFFFAOYSA-N 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000012456 homogeneous solution Substances 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- XIEKHWZMGUGSHG-UHFFFAOYSA-N (3,5,6-trichloro-2,2,3,4,4,5,6,6-octafluorohexanoyl) 3,5,6-trichloro-2,2,3,4,4,5,6,6-octafluorohexaneperoxoate Chemical compound FC(F)(Cl)C(F)(Cl)C(F)(F)C(F)(Cl)C(F)(F)C(=O)OOC(=O)C(F)(F)C(F)(Cl)C(F)(F)C(F)(Cl)C(F)(F)Cl XIEKHWZMGUGSHG-UHFFFAOYSA-N 0.000 description 1
- BOSAWIQFTJIYIS-UHFFFAOYSA-N 1,1,1-trichloro-2,2,2-trifluoroethane Chemical compound FC(F)(F)C(Cl)(Cl)Cl BOSAWIQFTJIYIS-UHFFFAOYSA-N 0.000 description 1
- 108010053481 Antifreeze Proteins Proteins 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 239000002041 carbon nanotube Substances 0.000 description 1
- 229910021393 carbon nanotube Inorganic materials 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000012067 mathematical method Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 230000028161 membrane depolarization Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000002114 nanocomposite Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
- 238000007669 thermal treatment Methods 0.000 description 1
- 238000001757 thermogravimetry curve Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10N—ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10N15/00—Thermoelectric devices without a junction of dissimilar materials; Thermomagnetic devices, e.g. using the Nernst-Ettingshausen effect
- H10N15/10—Thermoelectric devices using thermal change of the dielectric constant, e.g. working above and below the Curie point
- H10N15/15—Thermoelectric active materials
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F214/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
- C08F214/18—Monomers containing fluorine
- C08F214/22—Vinylidene fluoride
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F6/00—Post-polymerisation treatments
- C08F6/001—Removal of residual monomers by physical means
- C08F6/005—Removal of residual monomers by physical means from solid polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F6/00—Post-polymerisation treatments
- C08F6/06—Treatment of polymer solutions
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F6/00—Post-polymerisation treatments
- C08F6/06—Treatment of polymer solutions
- C08F6/12—Separation of polymers from solutions
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F6/00—Post-polymerisation treatments
- C08F6/26—Treatment of polymers prepared in bulk also solid polymers or polymer melts
- C08F6/28—Purification
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Treatments Of Macromolecular Shaped Articles (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/001,705 | 2004-12-02 | ||
| US11/001,705 US7323506B2 (en) | 2004-12-02 | 2004-12-02 | High performance P(VDF-TrFE) copolymer for pyroelectric conversion |
| PCT/CA2005/001745 WO2006058417A1 (en) | 2004-12-02 | 2005-11-17 | High performance p(vdf-trfe) copolymer for pyroelectric conversion |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2587345A1 CA2587345A1 (en) | 2006-06-08 |
| CA2587345C true CA2587345C (en) | 2010-03-30 |
Family
ID=36564710
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2587345A Expired - Fee Related CA2587345C (en) | 2004-12-02 | 2005-11-17 | High performance p(vdf-trfe) copolymer for pyroelectric conversion |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US7323506B2 (enExample) |
| EP (1) | EP1817351B1 (enExample) |
| JP (1) | JP2008521977A (enExample) |
| AT (1) | ATE481426T1 (enExample) |
| CA (1) | CA2587345C (enExample) |
| DE (1) | DE602005023641D1 (enExample) |
| WO (1) | WO2006058417A1 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8946538B2 (en) | 2009-05-14 | 2015-02-03 | The Neothermal Energy Company | Method and apparatus for generating electricity by thermally cycling an electrically polarizable material using heat from condensers |
| US8344585B2 (en) * | 2009-05-14 | 2013-01-01 | The Neothermal Energy Company | Method and apparatus for conversion of heat to electrical energy using a new thermodynamic cycle |
| US9166139B2 (en) | 2009-05-14 | 2015-10-20 | The Neothermal Energy Company | Method for thermally cycling an object including a polarizable material |
| US8350444B2 (en) * | 2009-05-14 | 2013-01-08 | The Neothermal Energy Company | Method and apparatus for conversion of heat to electrical energy using polarizable materials and an internally generated poling field |
| US8035274B2 (en) * | 2009-05-14 | 2011-10-11 | The Neothermal Energy Company | Apparatus and method for ferroelectric conversion of heat to electrical energy |
| CN102640331B (zh) * | 2009-08-28 | 2015-12-02 | 株式会社吴羽 | 非水系电池的电极形成用粘合剂溶液的制造方法及非水系电池的电极形成用粘合剂溶液 |
| US8519595B2 (en) | 2010-09-02 | 2013-08-27 | Ut-Battelle, Llc | MEMS based pyroelectric thermal energy harvester |
| EP2622729B1 (en) | 2010-09-29 | 2018-10-10 | The Neothermal Energy Company | Method and apparatus for generating electricity by thermally cycling an electrically polarizable material using heat from various sources and a vehicle comprising the apparatus |
| CN109467626A (zh) * | 2018-10-23 | 2019-03-15 | 浙江巨化技术中心有限公司 | 一种含氟聚合物树脂的后处理方法 |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2866721A (en) | 1955-03-15 | 1958-12-30 | Minnesota Mining & Mfg | Dispersion of fluorochlorocarbon polymers in a solution of a copolymer of trifluorochloroethylene with a halogenated olefin and method of coating surface therewith |
| US3193539A (en) | 1960-05-31 | 1965-07-06 | Pennsalt Chemicals Corp | Process for polymerizing vinylidene fluoride |
| US3441531A (en) * | 1966-01-17 | 1969-04-29 | Pennsalt Chemicals Corp | Vinylidene fluoride polymer dispersions having low viscosity |
| JPS5146919B1 (enExample) | 1971-02-09 | 1976-12-11 | ||
| US4173033A (en) | 1975-12-04 | 1979-10-30 | Daikin Kogyo Co., Ltd. | Polymeric dielectric for capacitors and the like consisting essentially of a vinylidene fluoride-trifluoroethylene copolymer |
| DE3011736A1 (de) | 1979-03-26 | 1980-10-09 | Daikin Ind Ltd | Polymeres piezoelektrisches material und verfahren zu dessen herstellung |
| US4620262A (en) | 1984-09-13 | 1986-10-28 | Olsen Randall B | Pyroelectric energy converter element comprising vinylidene fluoride-trifluoroethylene copolymer |
| GB8531738D0 (en) | 1985-12-24 | 1986-02-05 | Yarsley Technical Centre Ltd | Manufacture of fluorinated polymers |
| US4845193A (en) * | 1987-07-21 | 1989-07-04 | Mitsubishi Gas Chemical Co., Inc. | Process for producing polycarbonate resin molding material having low particle content with vented extruder |
| FR2624123B1 (fr) | 1987-12-08 | 1990-04-06 | Atochem | Copolymeres piezoelectriques de fluorure de vinylidene et de trifluoroethylene |
| JPH02197183A (ja) | 1988-03-29 | 1990-08-03 | Pennwalt Corp | 積層圧電構造及びその形成方法 |
| JPH0813861B2 (ja) * | 1989-03-17 | 1996-02-14 | 信越化学工業株式会社 | フッ化ビニリデン―トリフルオロメチルエチレン共重合体 |
| US5140082A (en) | 1989-03-17 | 1992-08-18 | Shin-Etsu Chemical Co., Ltd. | Vinylidene fluoride trifluoromethylethylene copolymer |
| JPH0473807A (ja) * | 1990-07-13 | 1992-03-09 | Tokyo Electric Power Co Inc:The | 強誘電材料 |
| JPH09229840A (ja) * | 1996-02-20 | 1997-09-05 | Nohmi Bosai Ltd | ガスセンサ |
| JP2002513514A (ja) | 1997-11-18 | 2002-05-08 | ザ ペンステート リサーチファウンデーション | 強誘電性のリラクサー・ポリマー |
| WO2000036656A1 (en) * | 1998-12-14 | 2000-06-22 | Her Majesty, The Queen, In Right Of Canada As Represented By The Minister Of Natural Resources | Pyroelectric conversion system |
| ITMI20011615A1 (it) * | 2001-07-26 | 2003-01-26 | Ausimont Spa | Processo di ottenimento di p0lveri fini non termoprocessabili di ptfeomopolimero o ptfe modificato |
| ITMI20011614A1 (it) * | 2001-07-26 | 2003-01-26 | Ausimont Spa | Processo di purificazione di copolimeri termoprocessabili del tetrafluoroetilene |
| US6713563B2 (en) | 2002-03-29 | 2004-03-30 | The United States Of America As Represented By The Secretary Of The Navy | Electrostrictive poly(vinylidene fluoride-co-trifluoroethylene) networks |
| WO2004029109A1 (ja) | 2002-09-25 | 2004-04-08 | Kureha Chemical Industry Company, Limited | ポリ弗化ビニリデン系共重合体及びその溶液 |
| EP1452551B1 (en) * | 2003-02-27 | 2006-09-06 | Rohm and Haas Electronic Materials, L.L.C. | A process of fractionating polymers |
-
2004
- 2004-12-02 US US11/001,705 patent/US7323506B2/en not_active Expired - Fee Related
-
2005
- 2005-11-17 EP EP05810773A patent/EP1817351B1/en not_active Expired - Lifetime
- 2005-11-17 DE DE602005023641T patent/DE602005023641D1/de not_active Expired - Lifetime
- 2005-11-17 AT AT05810773T patent/ATE481426T1/de not_active IP Right Cessation
- 2005-11-17 WO PCT/CA2005/001745 patent/WO2006058417A1/en not_active Ceased
- 2005-11-17 JP JP2007543667A patent/JP2008521977A/ja active Pending
- 2005-11-17 CA CA2587345A patent/CA2587345C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CA2587345A1 (en) | 2006-06-08 |
| EP1817351A1 (en) | 2007-08-15 |
| EP1817351B1 (en) | 2010-09-15 |
| JP2008521977A (ja) | 2008-06-26 |
| EP1817351A4 (en) | 2008-12-17 |
| DE602005023641D1 (de) | 2010-10-28 |
| ATE481426T1 (de) | 2010-10-15 |
| US7323506B2 (en) | 2008-01-29 |
| US20060122299A1 (en) | 2006-06-08 |
| WO2006058417A1 (en) | 2006-06-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed | ||
| MKLA | Lapsed |
Effective date: 20121119 |