WO2007056350A1 - Composition de fluoropolymere pour traitement par fusion - Google Patents

Composition de fluoropolymere pour traitement par fusion Download PDF

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Publication number
WO2007056350A1
WO2007056350A1 PCT/US2006/043306 US2006043306W WO2007056350A1 WO 2007056350 A1 WO2007056350 A1 WO 2007056350A1 US 2006043306 W US2006043306 W US 2006043306W WO 2007056350 A1 WO2007056350 A1 WO 2007056350A1
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WO
WIPO (PCT)
Prior art keywords
composition
ptfe
melt
pfa
ranges
Prior art date
Application number
PCT/US2006/043306
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English (en)
Inventor
Shinichi Namura
Original Assignee
Dupont-Mitsui Fluorochemicals Company, Ltd.
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Dupont-Mitsui Fluorochemicals Company, Ltd. filed Critical Dupont-Mitsui Fluorochemicals Company, Ltd.
Priority to CN2006800416275A priority Critical patent/CN101365750B/zh
Priority to EP06837041A priority patent/EP1948733A1/fr
Publication of WO2007056350A1 publication Critical patent/WO2007056350A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L27/00—Compositions of homopolymers or 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; Compositions of derivatives of such polymers
    • C08L27/02—Compositions of homopolymers or 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; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • C08L27/12—Compositions of homopolymers or 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; Compositions of derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms
    • C08L27/18—Homopolymers or copolymers or tetrafluoroethene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2205/00—Polymer mixtures characterised by other features
    • C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2205/00—Polymer mixtures characterised by other features
    • C08L2205/03—Polymer mixtures characterised by other features containing three or more polymers in a blend

Definitions

  • the present invention pertains to a fluoropolymer composition for melt processing having excellent resistance to chemical permeation.
  • PFA the copolymer of tetrafluoroethylene (TFE) and perfluoro(alkyl vinyl ether) (PAVE) has excellent resistance to heat and chemicals.
  • PFA is used for melt molding of articles such as pipes for transporting various types of chemical solutions, fitting of the pipes, in making or lining pipes, fittings, valves, transportation containers, storage containers, pumps, and filter housings used in the pharmaceutical industry, and in other processes such as chemical plants, and semiconductor manufacturing process or liquid crystal manufacturing process; and for lining of articles such as steel pipes, valves and fittings.
  • PFA is exposed to highly permeable chemicals such as sulfuric acid, hydrochloric acid, hydrofluoric acid, nitric acid, ammonia, their mixtures with hydrogen peroxide or ozone, developing or peeling solutions for photoresist to which a fluorinated surfactant is added, high-concentration ozone vapor, and ozone water.
  • highly permeable chemicals such as sulfuric acid, hydrochloric acid, hydrofluoric acid, nitric acid, ammonia, their mixtures with hydrogen peroxide or ozone, developing or peeling solutions for photoresist to which a fluorinated surfactant is added, high-concentration ozone vapor, and ozone water.
  • PFA having high durability, as measured by flex life (sometimes called MlT flex life) and improved resistance to chemical permeation is desired.
  • Nitrogen gas permeability is ordinarily used as a convenient measure to evaluate the permeability of PFA.
  • Patent No. 6,649,699 the permeation resistance of PFA is improved, by blending PFA with polytetrafluoroethylene (PTFE) having low molecular weight. It is reported that the permeation resistance is improved with the increase of the PTFE mixture ratio.
  • the low molecular weight PTFE is eith'era 1 MIIH ' lowabli 1 PTFE directly obtained by the polymerization of the
  • PTFE or a PTFE which is obtained by the thermal decomposition or radiolysis of high molecular weight (non-melt processible) PTFE.
  • the low molecular weight PTFE obtained by direct polymerization is preferably blended with PFA because it is less costly, than the low molecular weight PTFE obtained by special treatments such as radiolysis, and furthermore has excellent thermal stability, and is more easily obtained in high purity, it is preferable for blending with the PFA.
  • the amount of the blended PTFE is increased to a level of 20% or greater of the PFA plus PTFE composition, the improvement of the permeation resistance of the composition does not increase in proportion to the increase of the PTFE content.
  • the purpose of the present invention is to provide an improved composition composed of PFA and a melt-flowable PTFE directly obtained by the polymerization having improved resistance to chemical permeation.
  • the fluoropolymer composition for melt processing of the present invention is composed of three components of (A) PFA, (B) melt-flowable PTFE directly obtained by polymerizing TFE, and (C) PTFE with a low molecular weight obtained by the radiolysis of a non-melt flowable high molecular weight PTFE.
  • the weight ratio of AJ(B + C) ranges from 80/20 to 30/70, and the weight ratio of (A + B)/C ranges from 99.99/0.01 to 90/10.
  • the composition of the present invention has improved permeation resistance, compared with a composition composed of two components of PFA (A) and PTFE.
  • Figure 1 shows the apparatus used in a hydrochloric acid permeation test.
  • the PFA (A) of the present invention is a copolymer of TFE and PAVE that can be manufactured by conventional methods such as solution polymerization, emulsion polymerization, or suspension polymerization.
  • PAVE used in the copolymer can be that of Formula 1 or 2. Examples include copolymers of TFE with perfluoro(methyl vinyl ether) (PMVE). This polymer, sometimes referred to as MFA, usually includes some PPVE in addition to PMVE.
  • Preferred comonomers are perfluoro(propyl vinyl ether) (PPVE) and perfluoro(ethyl vinyl ether) (PEVE), of which the PEVE is the more preferred comonomer. (Formula 1)
  • X is H or F.
  • n is an integer of 0 to 4.
  • m is an integer of 0 to 7.
  • CF 3 CF 3 q is an integer of 0 to 3.
  • the PAVE content in the PFA (A) is preferably 3 wt% or greater of the total wt % of PFA. If the content is less than 3 wt%, the durability of the composition obtained by mixing PTFE is unsatisfactory.
  • the lower limit of the PAVE content is preferably 5 wt% of the total PFA wt %. In general, with the increase of the content, the durability of the composition is improved.
  • high-temperature mechanical properties of the molded » " ⁇ " ⁇ pro ⁇ iict ⁇ etfer ' ioratiV-TH'e-lbreferable upper limit of the PAVE content is 15 wt%, and more preferably 10 wt% of the total PFA wt%.
  • the PFA (A) used in the present invention it is preferable for the PFA (A) used in the present invention to have a melt flow rate (hereinafter, abbreviated to MFR) of 0.01 g/10 min or 5 greater.
  • MFR melt flow rate
  • the preferred lower limit of the MFR is 0.05 g/10 min.
  • the upper limit of the MFR that can maintain a good durability is 100 g/10 min, preferably 70 g/10 min, and more preferably 40
  • PFA with an MFR of less than 0.01 g/10 min and PFA with an MFR of greater than 0.01 g/10 min can also be mixed to adjust the MFR between the above-mentioned upper limit and lower limit.
  • the PTFE (B) and the PTFE (C) are mixed with the above-mentioned PFA (A). Both the PTFE (B) and (C) are TFE
  • the PTFE (B) is a melt-flowable PTFE (that is, the melt flow rate can be measured by the method described in the Examples) directly
  • the MFR is not particularly limited but is usually selected from a range of 1 ,000
  • PTFE (B) can be manufactured by conventional methods such as solvent polymerization, emulsion polymerization, and suspension polymerization of TFE.
  • solvent polymerization emulsion polymerization
  • emulsion polymerization emulsion polymerization
  • suspension polymerization emulsion polymerization
  • PTFE (C) is a PTFE with a low molecular weight obtained by radiolysis of a non-melt flowable PTFE of high molecular weight.
  • Such non-melt flowable PTFE is often called "molding powder" or "fine powder.” Since the melt flowablity increases with decreasing molecular weight of the PTFE, the extent of decrease of the molecular weight can be , , om MFR of the PTFE as a function of degree of irradiation.
  • the PTFE (C) in the present invention has an MFR of 0.01 g/10 min or greater, and preferably 0.1 g/10 min or greater. If the MFR is less than 0.01 g/10 min, uniform dispersion of the PTFE in the composition is difficult.
  • the upper limit of the MFR is not particularly limited but is preferably in the range of 1 ,000 g/10 min or less.
  • the PTFE (C) can be manufactured by irradiation with gamma rays or an electron beam of the above-mentioned "molding powder” or "fine powder” at a temperature lower than the melting temperature under vacuum or in air or in an inert gas atmosphere until the radiation dose reaches 10 kGy-1 MGy.
  • the reaction is disclosed in Japanese Kokoku Patent Nos. Sho 47[1972]- 19609, Sho 52[1977]-38870, and GB 1 ,406,238.
  • the size of the PTFE (B) and the PTFE (C) particles are not particularly limited, and a powder with an average particle diameter of 0.01-100 ⁇ m can be used. A uniform composition is more easily obtained if the average particle diameter is preferably 0.05-50 ⁇ m, and more preferably 0.05-25 ⁇ m.
  • the above-mentioned PFA (A), PTFE (B), and PTFE (C) of the composition of the present invention are mixed in the weight ratio of A/(B + C) ranging from 80/20 to 30/70, and preferably ranging from 80/20 to 40/60, and more preferably ranging from 80/20 to 50/50. If the content of (B + C) is less than 20 wt%, the improvement of the permeation resistance is small, and if the content is more than 70 wt%, durability and mechanical strength of the composition decrease.
  • the composition of the present invention in which the PTFE component is composed of (B) and (C) has a permeation resistance improved by 20% or more compared to the permeation of PFA itself.
  • the ratio (A + B ) to C is in the range of 99.99/0.01 to 90/10 as the weight ratio of the PTFE (C), a sufficient improvement effect is obtained. If the ratio is less than 0.01 wt%, significant improvement in permeation resistance is not observed. The mixture ratio of more than 10 wt% tends to decrease the durability of the composition.
  • the (A + B)/C weight ratio is preferably 99.9/0.1 to 95/5, and more preferably 99/1 to 95/5. , mpoa ⁇ d of the above-mentioned PFA (A),
  • PTFE (B) 1 and PTFE (C) of the present invention can be melt processed and has an MFR of 0.1-100 g/10 min. If the MFR is less than 0.1 g/10 min, melt processing is difficult. If it is more than 100 g/10 min, the durability of the composition is unsatisfactory.
  • the MFR is preferably 0.5- 50 g/10 min.
  • the MFR of the composition can be estimated using the following equation.
  • (1/MFR of the composition) 1734 (weight % of PFA (A)) (1/MFR of PFA (A)) 1734 + (weight % of PTFE (B)) (1/MFR of PTFE (B)) 1734 + (weight % of PTFE (C)) (1/MFR of PTFE (C)) 1/34 .
  • the MFR of the composition sometimes deviates slightly from the numerical value obtained using the above-mentioned relation equation because of thermal decomposition or coupling phenomenon of the polymers during mixing or such post-treatments as fluorination
  • the MFR of the PFA (A), the PTFE (B), and the PTFE (C) can be estimated by taking this variation into consideration so that the MFR of the final composition will be in the desired range.
  • the PTFE In the manufacture of the composition of the present invention, if the PTFE is not well mixed, durability of articles made from the composition will be reduced. Therefore it is preferable to charge the PFA (A), the PTFE (B), and the PTFE (C) into a batch type or continuous kneader or coaxial extruder and to uniformly melt-knead the ingredients.
  • the PFA and PTFE powders can also be mixed in advance by dry or wet blending before melt-kneading. By wet blending is meant the mixing of dispersions of the PFA and one or both of the PTFEs.
  • These dispersions may be the dispersions obtained by aqueous dispersion polymerization of PFA and the PTFE made by polymerizing TFE to the desired low molecular weight, or the dispersions may be made from the polymer in powder form by dispersing the powder in preferably aqueous medium with a dispersing agent, such as a surfactant. After blending, the polymers are isolated from the dispersion medium.
  • a dispersing agent such as a surfactant
  • the mixture can be obtained by adding the PTFE (B) and PTFE (C) to a polymerization medium in a polymerization vessel in a ⁇ ro n ⁇ l & polym ⁇ rizatlon of TFE and PAVE to make PFA (A).
  • the PTFE (C) can be mixed with a powder of core/shell construction, which is obtained by adding particles of the PFA (A) to a polymerization medium in advance and initiating polymerization of the PTFE (B).
  • the PFA and the PTFE are preferably fluorinated before or after melt-kneading by the method described in U.S. Patent No. 4,743,658 and thereby reduce unstable end groups, to reduce the elution of fluorine ions, or to the improve the ozone resistance of articles made from the composition.
  • an improved resistance to chemical permeation can be obtained by mixing only a small amount of the higher cost PTFE (C) in addition to the PTFE (B), so that the cost penalty is minimized.
  • the PTFE has excellent heat resistance, chemical resistance, and purity similarly to that of the PFA, the composition of the present invention is suitable for a melt fabrication of parts for transferring various chemical solutions used in manufacturing processes of products such as chemicals, semiconductors and liquid crystal polymers.
  • Examples of articles made from the composition of the present invention include tubes, pipes, hoses, films, sheets, round bars, and square rods by extrusion; moldings, fittings, filter housings, valves, pumps, containers, wafer carriers, vessels, tanks, flow meters by injection molding; containers such as bottles by blow molding or rotation molding; lining of valves, pumps, pipes, joints, by transfer molding; lining of steel, such as steel containers, tanks, pipes, by rotation molding; and sheets, by compression molding.
  • PAVE content A sample was melt compressed at 350 0 C and cooled with water, so that a film with a thickness of about 50 ⁇ m was obtained. From the infrared absorption spectrum (in nitrogen atmosphere) of the film, the 1 . . , ,. " ra Vf "Content was ⁇ ' etermined according to the method described in U.S.
  • Melt flow rate (MFR): Using a melt indexer (made by Toyo Seiki Co., Ltd.) equipped with corrosion-resistant cylinder, die, and piston according to ASTM D1238-95, a 5 g sample was filled in the cylinder held at 372 ⁇ 1 0 C.
  • the sample was held for 5 min, and extruded through the die orifice under a load (piston and weight) of 5 kg.
  • the extrusion rate of the melt was measured and reported as the MFR.
  • Nitrogen gas permeability A film with a thickness of 0.25-0.35 mm prepared by a compression molding at 350 0 C was used for measuring the permeability at a temperature of 23 0 C by an S-69 type gas and water vapor permeability measurement device made by Shibata Kagaku Kikai
  • the above ingredients were blended by melt-kneading them at
  • compositions are obtained by melt- kneading similarly to Example 1.
  • the properties of the compositions are summarized in Table II. As in Table 1 , there is a large synergistic effect of
  • Amount mixed PFA 40 40 (part by weight) PTFE (B) 60 58.5 PTFE (C) 0 1.5

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
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Abstract

L’invention concerne une composition présentant une excellente résistance à la perméation chimique, comprenant (A) un copolymère tétrafluoroéthylène-perfluoro(alkyle vinyle éther), (B) un polytétrafluoroéthylène fluidifiable par fusion directement obtenu par polymérisation de tétrafluoroéthylène et (C) un polytétrafluoroéthylène de faible poids moléculaire obtenu par radiolyse d’un polytétrafluoroéthylène non fluidifiable par fusion de poids moléculaire élevé ; le rapport massique de A/(B + C) étant compris entre 80/20 et 30/70 ; et le rapport massique de (A + B)/C étant compris entre 99,99/0,01 et 90/10.
PCT/US2006/043306 2005-11-08 2006-11-07 Composition de fluoropolymere pour traitement par fusion WO2007056350A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
CN2006800416275A CN101365750B (zh) 2005-11-08 2006-11-07 用于熔融加工的含氟聚合物组合物
EP06837041A EP1948733A1 (fr) 2005-11-08 2006-11-07 Composition de fluoropolymere pour traitement par fusion

Applications Claiming Priority (2)

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JP2005323686A JP5106771B2 (ja) 2005-11-08 2005-11-08 路面標示計測装置
JP2005-323686 2005-11-08

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009076445A1 (fr) * 2007-12-12 2009-06-18 E. I. Du Pont De Nemours And Company Processus de moulage par extrusion-soufflage d'un polymère cœur-écorce et d'un fluoropolymère
WO2009076450A1 (fr) 2007-12-12 2009-06-18 E. I. Du Pont De Nemours And Company Processus d'obtention de feuille soufflée d'un mélange de polymère cœur-écorce et de fluoropolymère
WO2011075351A1 (fr) * 2009-12-18 2011-06-23 Whitford Corporation Compositions à base d'un mélange de polymères fluorés contenant de multiples polymères fluorés pouvant être mis en œuvre à l'état fondu
US20130137812A1 (en) * 2008-09-26 2013-05-30 Whitford Corporation Blended fluoropolymer compositions and coatings for flexible substrates
CN115584094A (zh) * 2018-06-07 2023-01-10 科慕·三井氟产品株式会社 可熔融加工的氟树脂组合物以及由其形成的注塑制品

Families Citing this family (4)

* Cited by examiner, † Cited by third party
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DE102008037682A1 (de) 2008-08-14 2010-04-08 Strackharn, Klaus, Dr.med. Verwendung äquipotenter Dosierungen von Lokalanästetika oder Derivaten davon zur Therapie chronischer Schmerzen
CN104093756B (zh) * 2012-02-08 2016-09-28 纳幕尔杜邦公司 芯/壳含氟聚合物
JP6337504B2 (ja) * 2014-02-21 2018-06-06 株式会社リコー 画像処理装置、移動体、ロボット、機器制御方法およびプログラム
CN104558365B (zh) * 2014-12-24 2016-10-05 上海三爱富新材料股份有限公司 可熔性聚四氟乙烯的制备方法

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995001401A1 (fr) * 1993-06-30 1995-01-12 Dupont-Mitsui Fluorochemicals Co., Ltd. Composition copolymere au tetrafluoroethylene/fluoroalcoxy trifluoroethylene
WO2002044266A2 (fr) * 2000-11-30 2002-06-06 E.I. Dupont De Nemours And Company Compositions fluoropolymeres dotees d'une impermeabilite au gaz amelioree

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JP3818641B2 (ja) * 2001-11-30 2006-09-06 トヨタ自動車株式会社 車両用走路判定装置および車両制御装置
JP2004228847A (ja) * 2003-01-22 2004-08-12 Hitachi Ltd 車載用カメラ装置
JP2004297306A (ja) * 2003-03-26 2004-10-21 Pasuko:Kk 道路、河川の映像撮影装置及び映像データの再生装置
JP4262566B2 (ja) * 2003-10-16 2009-05-13 株式会社日立製作所 車載用撮像装置及びカメラ
JP4273119B2 (ja) * 2003-10-21 2009-06-03 和郎 岩根 ナビゲーション装置

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995001401A1 (fr) * 1993-06-30 1995-01-12 Dupont-Mitsui Fluorochemicals Co., Ltd. Composition copolymere au tetrafluoroethylene/fluoroalcoxy trifluoroethylene
WO2002044266A2 (fr) * 2000-11-30 2002-06-06 E.I. Dupont De Nemours And Company Compositions fluoropolymeres dotees d'une impermeabilite au gaz amelioree

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009076445A1 (fr) * 2007-12-12 2009-06-18 E. I. Du Pont De Nemours And Company Processus de moulage par extrusion-soufflage d'un polymère cœur-écorce et d'un fluoropolymère
WO2009076450A1 (fr) 2007-12-12 2009-06-18 E. I. Du Pont De Nemours And Company Processus d'obtention de feuille soufflée d'un mélange de polymère cœur-écorce et de fluoropolymère
EP2219847A1 (fr) * 2007-12-12 2010-08-25 E. I. du Pont de Nemours and Company Processus d'obtention de feuille soufflée d'un mélange de polymère c ur-écorce et de fluoropolymère
US8192677B2 (en) 2007-12-12 2012-06-05 E. I. Du Pont De Nemours And Company Core/shell polymer and fluoropolymer blending blow molding and blown film process
US20130137812A1 (en) * 2008-09-26 2013-05-30 Whitford Corporation Blended fluoropolymer compositions and coatings for flexible substrates
US9090778B2 (en) * 2008-09-26 2015-07-28 Whitford Corporation Blended fluoropolymer compositions and coatings for flexible substrates
WO2011075351A1 (fr) * 2009-12-18 2011-06-23 Whitford Corporation Compositions à base d'un mélange de polymères fluorés contenant de multiples polymères fluorés pouvant être mis en œuvre à l'état fondu
JP2013514435A (ja) * 2009-12-18 2013-04-25 ウィットフォード コーポレーション 複数の溶融加工可能なフルオロポリマーを含有するブレンドフルオロポリマー組成物
US9051461B2 (en) 2009-12-18 2015-06-09 Whitford Corporation Blended fluoropolymer compositions having multiple melt processible fluoropolymers
CN115584094A (zh) * 2018-06-07 2023-01-10 科慕·三井氟产品株式会社 可熔融加工的氟树脂组合物以及由其形成的注塑制品

Also Published As

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CN101365750B (zh) 2011-05-25
JP5106771B2 (ja) 2012-12-26
CN101365750A (zh) 2009-02-11
JP2007133007A (ja) 2007-05-31
EP1948733A1 (fr) 2008-07-30

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