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 US7323506B2 (en) | 2004-12-02 | 2004-12-02 | High performance P(VDF-TrFE) copolymer for pyroelectric conversion |
| US11/001,705 | 2004-12-02 | ||
| 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 (https=) |
| EP (1) | EP1817351B1 (https=) |
| JP (1) | JP2008521977A (https=) |
| AT (1) | ATE481426T1 (https=) |
| CA (1) | CA2587345C (https=) |
| DE (1) | DE602005023641D1 (https=) |
| WO (1) | WO2006058417A1 (https=) |
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 |
| US8035274B2 (en) * | 2009-05-14 | 2011-10-11 | The Neothermal Energy Company | Apparatus and method for ferroelectric conversion of heat to electrical energy |
| 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 |
| US9166139B2 (en) * | 2009-05-14 | 2015-10-20 | The Neothermal Energy Company | Method for thermally cycling an object including a polarizable material |
| US9000076B2 (en) * | 2009-08-28 | 2015-04-07 | Kureha Corporation | Process for producing non-aqueous battery electrode-forming binder solutions, and non-aqueous battery electrode-forming binder solution |
| US8519595B2 (en) | 2010-09-02 | 2013-08-27 | Ut-Battelle, Llc | MEMS based pyroelectric thermal energy harvester |
| WO2012050906A1 (en) * | 2010-09-29 | 2012-04-19 | 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 (https=) | 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 |
| DE3050408C2 (de) | 1979-03-26 | 1985-06-13 | Daikin Kogyo Co., Ltd., Osaka | Piezoelektrisches, verstrecktes, polarisiertes Vinylidenfluorid-Trifluorethylen-Copolymer 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 |
| EP0300485A3 (en) * | 1987-07-21 | 1990-04-25 | Mitsubishi Gas Chemical Company, Inc. | Process for producing polycarbonate resin molding material with low particle content |
| 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 |
| DE69837624T2 (de) | 1998-12-14 | 2007-12-27 | Her Majesty The Queen In Right Of Canada As Represented By The Minister Of Natural Resources, Ottawa | Pyroelektrisches umwandlungssystem |
| ITMI20011614A1 (it) * | 2001-07-26 | 2003-01-26 | Ausimont Spa | Processo di purificazione di copolimeri termoprocessabili del tetrafluoroetilene |
| ITMI20011615A1 (it) * | 2001-07-26 | 2003-01-26 | Ausimont Spa | Processo di ottenimento di p0lveri fini non termoprocessabili di ptfeomopolimero o ptfe modificato |
| 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 |
| EP1568719B1 (en) | 2002-09-25 | 2010-04-14 | Kureha Corporation | Process for preparing polyvinylidene fluoride copolymer |
| DE602004002219T2 (de) * | 2003-02-27 | 2007-08-02 | Rohm and Haas Electronic Materials, L.L.C., Marlborough | Verfahren zur Trennung von Polymeren |
-
2004
- 2004-12-02 US US11/001,705 patent/US7323506B2/en not_active Expired - Fee Related
-
2005
- 2005-11-17 AT AT05810773T patent/ATE481426T1/de not_active IP Right Cessation
- 2005-11-17 CA CA2587345A patent/CA2587345C/en not_active Expired - Fee Related
- 2005-11-17 WO PCT/CA2005/001745 patent/WO2006058417A1/en not_active Ceased
- 2005-11-17 DE DE602005023641T patent/DE602005023641D1/de not_active Expired - Lifetime
- 2005-11-17 EP EP05810773A patent/EP1817351B1/en not_active Expired - Lifetime
- 2005-11-17 JP JP2007543667A patent/JP2008521977A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| WO2006058417A1 (en) | 2006-06-08 |
| US20060122299A1 (en) | 2006-06-08 |
| DE602005023641D1 (de) | 2010-10-28 |
| EP1817351A4 (en) | 2008-12-17 |
| CA2587345A1 (en) | 2006-06-08 |
| EP1817351A1 (en) | 2007-08-15 |
| EP1817351B1 (en) | 2010-09-15 |
| US7323506B2 (en) | 2008-01-29 |
| JP2008521977A (ja) | 2008-06-26 |
| ATE481426T1 (de) | 2010-10-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed | ||
| MKLA | Lapsed |
Effective date: 20121119 |