ES2611988T3 - Polimerización de fluoropolímeros usando tensioactivos no fluorados - Google Patents
Polimerización de fluoropolímeros usando tensioactivos no fluorados Download PDFInfo
- Publication number
- ES2611988T3 ES2611988T3 ES06773949.0T ES06773949T ES2611988T3 ES 2611988 T3 ES2611988 T3 ES 2611988T3 ES 06773949 T ES06773949 T ES 06773949T ES 2611988 T3 ES2611988 T3 ES 2611988T3
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- Prior art keywords
- fluorinated
- weight
- poly
- polymerization
- vinylidene fluoride
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- 239000004094 surface-active agent Substances 0.000 title abstract description 7
- 238000006116 polymerization reaction Methods 0.000 title abstract description 4
- 229920002313 fluoropolymer Polymers 0.000 title abstract 2
- 239000004811 fluoropolymer Substances 0.000 title abstract 2
- 239000003999 initiator Substances 0.000 abstract description 11
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 abstract description 10
- 229920002125 Sokalan® Polymers 0.000 abstract description 5
- -1 trifluoroethylene, chlorotrifluoroethylene Chemical group 0.000 abstract description 3
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical class C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 abstract 2
- NDMMKOCNFSTXRU-UHFFFAOYSA-N 1,1,2,3,3-pentafluoroprop-1-ene Chemical compound FC(F)C(F)=C(F)F NDMMKOCNFSTXRU-UHFFFAOYSA-N 0.000 abstract 1
- ABADUMLIAZCWJD-UHFFFAOYSA-N 1,3-dioxole Chemical class C1OC=CO1 ABADUMLIAZCWJD-UHFFFAOYSA-N 0.000 abstract 1
- QMIWYOZFFSLIAK-UHFFFAOYSA-N 3,3,3-trifluoro-2-(trifluoromethyl)prop-1-ene Chemical group FC(F)(F)C(=C)C(F)(F)F QMIWYOZFFSLIAK-UHFFFAOYSA-N 0.000 abstract 1
- FDMFUZHCIRHGRG-UHFFFAOYSA-N 3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C=C FDMFUZHCIRHGRG-UHFFFAOYSA-N 0.000 abstract 1
- GVEUEBXMTMZVSD-UHFFFAOYSA-N 3,3,4,4,5,5,6,6,6-nonafluorohex-1-ene Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C=C GVEUEBXMTMZVSD-UHFFFAOYSA-N 0.000 abstract 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 abstract 1
- 239000012431 aqueous reaction media Substances 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 abstract 1
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical compound FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 abstract 1
- 229920002554 vinyl polymer Polymers 0.000 abstract 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000007787 solid Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000178 monomer Substances 0.000 description 3
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 3
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 239000002033 PVDF binder Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000004816 latex Substances 0.000 description 2
- 229920000126 latex Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
Classifications
-
- 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
- C08F14/00—Homopolymers and 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
- C08F14/18—Monomers containing fluorine
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/04—Polymerisation in solution
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/12—Polymerisation in non-solvents
- C08F2/16—Aqueous medium
- C08F2/22—Emulsion polymerisation
-
- 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
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- 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)
- Polymerisation Methods In General (AREA)
Abstract
Un proceso para preparar un fluoropolímero en un medio de reacción acuoso que comprende: a) formar una emulsión acuosa que comprende al menos un iniciador de radicales, al menos un tensioactivo no fluorado, y al menos un fluoromonómero seleccionado entre el grupo que consiste en: fluoruro de vinilideno, tetrafluoroetileno, trifluoroetileno, clorotrifluoroetileno, hexafluoropropeno, fluoruro de vinilo, hexafluoroisobutileno, perfluorobutiletileno, pentafluoropropeno, 3,3,3-trifluoro-1-propeno, 2-trifluorometil- 3,3,3-trifluoropropeno , un éter vinílico fluorado, un éter alílico fluorado, un éter alílico no fluorado, un dioxol fluorado y sus combinaciones, e b) iniciar la polimerización de dicho fluoromonómero, en el que dicho tensioactivo no fluorado es un poliácido seleccionado entre el grupo que consiste en poli(ácido vinil fosfónico), poli(ácido acrílico), poli(ácido vinil sulfónico) y sus sales.
Description
peso del monómero de fluoruro de vinilideno.
Ejemplo 8:
Se preparó poli(fluoruro de vinilideno) usando un tensioactivo de polisiloxano T-5863 y un Iniciador de Persulfato de Potasio (KPS). Se usó agua desionizada. Los reactivos fueron de calidad de reactivo ACS a menos que se afirme lo 5 contrario. Se recibió poli(ácido acrílico) en forma de solución de 45 % en peso y T-5863 fue 100 % puro. A un reactor de acero inoxidable de 7,5 litros, se añadieron 4030 g de agua, 4 g cera de parafina, 100,0 g de una solución acuosa de tensioactivo de 0,41 % en peso en poli(ácido acrílico) y 1,9 % en peso de T-5863, y 350 g de una solución acuosa de iniciador de 0,5 % en peso de persulfato de potasio y 0,31 % en peso de acetato de sodio. Se purgó la mezcla con argón y se agitó durante 0,5 horas. Se selló el reactor, se continuó la agitación, y se calentó el reactor hasta 82 10 grados Celsius. Se introdujeron 478 g de fluoruro de vinilideno en el reactor a una presión de 4454 kPa. En primer lugar se introdujeron 64 g de solución de iniciador a 36 g/h seguido de una alimentación estacionaria de una solución de iniciador durante toda la reacción. La temperatura de reacción se mantuvo en 121 grados Celsius y se mantuvo la presión de reacción en 4480 kPa por medio de la adición de fluoruro de vinilideno necesario. Trascurridas 2,6 horas, se detuvo la alimentación de fluoruro de vinilideno. Se había añadido una cantidad de 2200 g de fluoruro de 15 vinilideno al reactor. Durante un período de 0,3 horas, se continuó la agitación, se mantuvo la temperatura, y se continuó la alimentación de una solución acuosa de iniciador. Se detuvo la alimentación del iniciador acuoso, y después durante un período de 0,17 horas, se mantuvieron la agitación y la temperatura de reacción. La agitación y el calentamiento fueron discontinuos. Tras el enfriamiento hasta temperatura ambiente, se purgó el gas de exceso, y se vació el reactor de látex a través de la malla de acero inoxidable. Se había formado un coágulo de
20 aproximadamente 0,8 % en peso durante la reacción. Las mediciones gravimétricas de sólidos del látex mostraron que el polímero sólido presentó un rendimiento de 90,3 % en peso, basado en el peso de fluoruro de vinilideno alimentado al reactor. La cantidad de persulfato de potasio, que se usó para convertir el monómero en polímero, fue de un 0,104 % en peso, basado en el peso del monómero de fluoruro de vinilideno.
Tabla 2: Reacciones de polimerización de PVDF usando poli(ácido acrílico) como único tensioactivo. Todas las 25 concentraciones son en VDF.
- Número de Ejemplo
- Conc. Tens. ppm Tipo deIniciador Conc. Iniciador ppm Temp. Reacción ºC Sólidos % en peso Rendimiento % en peso Coagulo% en peso
- 5
- 572 KPS 1323 121 29,7 88,5 1,0
- 6
- 591 KPS 709 121 32,2 98,6 0,5
- 7
- 286 KPS 454 121 31,2 93,1 0,9
Tabla 3: Reacciones de polimerización de PVDF usando tensioactivos mixtos de poli(ácido acrílico)/polisiloxano T5863. Todas las concentraciones son en VDF.
- Número de Ejemplo
- Conc. PPA. ppm Conc. T-5863 ppm Tipo deIniciador Conc. Iniciador ppm Temp. Reacción ºC Sólidos % en peso Rendimiento % en peso Coagulo % en peso
- 8
- 184 864 KPS 1042 82 30,2 90,2 0,82
8
Claims (1)
-
imagen1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US70646405P | 2005-08-08 | 2005-08-08 | |
| US706464P | 2005-08-08 | ||
| PCT/US2006/024704 WO2007018783A2 (en) | 2005-08-08 | 2006-06-26 | Polymerization of fluoropolymers using non-fluorinated surfactants |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2611988T3 true ES2611988T3 (es) | 2017-05-11 |
Family
ID=37727793
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES06773949.0T Active ES2611988T3 (es) | 2005-08-08 | 2006-06-26 | Polimerización de fluoropolímeros usando tensioactivos no fluorados |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US8697822B2 (es) |
| EP (1) | EP1922340B1 (es) |
| JP (1) | JP5106396B2 (es) |
| KR (1) | KR101298057B1 (es) |
| CN (1) | CN101243108B (es) |
| ES (1) | ES2611988T3 (es) |
| WO (1) | WO2007018783A2 (es) |
Families Citing this family (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8557938B2 (en) * | 2005-11-10 | 2013-10-15 | Arkema Inc. | Branched fluoropolymers |
| CN101293940B (zh) * | 2007-04-29 | 2012-11-21 | 上海远东氟材料技术有限公司 | 拒水拒油的含氟丙烯酸阳离子/非离子表面活性剂的制备方法 |
| JP5721741B2 (ja) * | 2009-12-18 | 2015-05-20 | ソルヴェイ・スペシャルティ・ポリマーズ・イタリー・エッセ・ピ・ア | フッ化ビニリデンポリマーの分散系の製造方法 |
| US9434837B2 (en) | 2010-09-01 | 2016-09-06 | Arkema Inc. | Method of producing fluoropolymers using acid-functionalized monomers |
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| US9574027B2 (en) | 2013-03-11 | 2017-02-21 | The Chemours Company Fc, Llc | Fluoropolymer resin treatment employing sorbent to reduce fluoropolymer resin discoloration |
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| EP3697823B1 (en) * | 2017-10-17 | 2024-01-24 | Solvay Specialty Polymers Italy S.p.A. | Method for the synthesis of fluoropolymers |
| CN112041358B (zh) * | 2018-04-27 | 2023-08-18 | Ａｇｃ株式会社 | 改性聚四氟乙烯的制造方法、改性聚四氟乙烯粉末的制造方法、延伸多孔体的制造方法 |
| GB201807544D0 (en) | 2018-05-09 | 2018-06-20 | 3M Innovative Properties Co | Fluoropolymers with very low amounts of a fluorinated alkanoic acid or its salts |
| EP3891220A4 (en) | 2018-12-06 | 2022-08-31 | Arkema, Inc. | FLUOROTHERMOPLASTIC ELASTOMERIC COMPOUNDS |
| JP7299513B2 (ja) * | 2019-02-05 | 2023-06-28 | ダイキン工業株式会社 | テトラフルオロエチレン重合体の製造方法及び組成物 |
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| EP3767710A1 (en) | 2019-07-15 | 2021-01-20 | Arkema France | Waterbased pvdf slurry formulation for silicon graphite anodes |
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2006
- 2006-06-26 JP JP2008526003A patent/JP5106396B2/ja active Active
- 2006-06-26 KR KR1020087003228A patent/KR101298057B1/ko active Active
- 2006-06-26 ES ES06773949.0T patent/ES2611988T3/es active Active
- 2006-06-26 EP EP06773949.0A patent/EP1922340B1/en active Active
- 2006-06-26 WO PCT/US2006/024704 patent/WO2007018783A2/en active Application Filing
- 2006-06-26 US US11/995,593 patent/US8697822B2/en active Active
- 2006-06-26 CN CN2006800294282A patent/CN101243108B/zh active Active
Also Published As
| Publication number | Publication date |
|---|---|
| WO2007018783A2 (en) | 2007-02-15 |
| KR101298057B1 (ko) | 2013-08-20 |
| JP2009504841A (ja) | 2009-02-05 |
| CN101243108B (zh) | 2012-08-22 |
| EP1922340A2 (en) | 2008-05-21 |
| US8697822B2 (en) | 2014-04-15 |
| US20090221776A1 (en) | 2009-09-03 |
| EP1922340B1 (en) | 2016-12-28 |
| WO2007018783A3 (en) | 2007-04-05 |
| KR20080032170A (ko) | 2008-04-14 |
| CN101243108A (zh) | 2008-08-13 |
| EP1922340A4 (en) | 2009-06-03 |
| JP5106396B2 (ja) | 2012-12-26 |
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