WO2005017017A1 - Curable perfluoroelastomer composition - Google Patents
Curable perfluoroelastomer composition Download PDFInfo
- Publication number
- WO2005017017A1 WO2005017017A1 PCT/US2004/026285 US2004026285W WO2005017017A1 WO 2005017017 A1 WO2005017017 A1 WO 2005017017A1 US 2004026285 W US2004026285 W US 2004026285W WO 2005017017 A1 WO2005017017 A1 WO 2005017017A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- curable composition
- perfluoroelastomer
- group
- hydrophobic
- bis
- Prior art date
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/34—Silicon-containing compounds
- C08K3/36—Silica
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
Definitions
- perfluoroelastomer compositions comprising a) perfluoroelastomer, b) a curative selected from the group consisting of an ammonia generating curative and a bis(aminophenol), and c) hydrophobic silica filler.
- Perfluoroelastomers have achieved outstanding commercial success and are used in a wide variety of applications in which severe environments are encountered, in particular those end uses where exposure to high temperatures and aggressive chemicals occurs. These polymers are often used in seals for aircraft engines, in oil-well drilling devices, in semiconductor wafer manufacturing processes and in sealing elements for industrial equipment used at high temperatures. Many perfluoroelastomer seals are filled with carbon black. However, an increasing number of end use applications require non-black seals. White fillers such as silica, barium sulfate, alumina and aluminum silicate are generally employed for such applications (U.S. Patent Nos. 5,696,189 and 6,191 ,208 B1).
- an aspect of the present invention is a curable composition
- a curable composition comprising A. a perfluoroelastomer comprising copolymerized units of (1 ) tetrafluoroethylene, (2) a perfluoro(vinyl ether), and (3) a cure site monomer selected from the group consisting of nitrile-containing fluorinated olefins and nitrile-containing fluorinated vinyl ethers; B.
- a curative selected from the group consisting of i) a bis(aminophenol) and ii) a compound that decomposes at temperatures between 40° and 330°C to produce ammonia.
- compositions of the present invention are based on elastomeric perfluoropolymers (hereinafter “perfluoroelastomers”), that is, substantially fully fluorinated fluoropolymers which, when cured, exhibit an elastomeric character.
- the perfluoroelastomers contain nitrile groups which render the polymers crosslinkable by ammonia and bis(aminophenols).
- Perfluoroelastomers are polymeric compositions having copolymerized units of at least two principal perfluorinated monomers. Generally, one of the principal comonomers is a perfluoroolefin, while the other is a perfluoro(vinyl ether).
- perfluorinated olefins include tetrafluoroethylene (TFE) and hexafluoropropylene (HFP).
- R f and R f are different linear or branched perfluoroalkylene groups of 2-6 carbon atoms, m and n are independently 0-10, and R f is a perfluoroalkyl group of 1-6 carbon atoms.
- a preferred class of perfluoro(vinyl ethers) includes compositions of the formula
- CF 2 CFO(CF 2 CFXO)nRf (II) where X is F or CF3, n is 0-5, and Rf is a perfluoroalkyl group of 1-6 carbon atoms.
- a most preferred class of perfluoro(vinyl ethers) includes those ethers wherein n is 0 or 1 and R f contains 1-3 carbon atoms. Examples of such perfluorinated ethers include perfluoro(methyl vinyl ether) (PMVE) and perfluoro(propyl vinyl ether) (PPVE).
- Other useful monomers include compounds of the formula
- Another example of a useful perfluoro(vinyl ether) includes
- Mixtures of perfluoro(vinyl ethers) may also be used.
- Preferred perfluoroelastomers are composed of tetrafluoroethylene and at least one perfluoro(vinyl ether) as principal monomer units. In such copolymers, the copolymerized perfluorinated ether units constitute from about 15 mole percent to 65 mole percent (preferably 25 to 60 mole percent) of total monomer units in the polymer.
- the perfluoropolymer further contains copolymerized units of at least one nitrile group-containing cure site monomer, generally in amounts of from 0.1-5 mole percent. The range is preferably between 0.3-1.5 mole percent.
- Suitable cure site monomers include nitrile-containing fluorinated olefins and nitrile-containing fluorinated vinyl ethers.
- cure site monomers are perfluorinated polyethers having a nitrile group and a trifluorovinyl ether group.
- a most preferred cure site monomer is
- perfluoroelastomers employed in this invention preferably comprise copolymerized units of i) 38.5 to 74.7 (most preferably 44 to 69.5) mole percent tetrafluoroethylene (TFE), ii) 25 to 60 (most preferably 30 to 55) mole percent perfluoro(methyl vinyl ether) (PMVE) and iii) 0.3 to 1.5 (most preferably 0.5 to 1.0) mole percent of a nitrile group - containing cure monomer, preferably 8-CNVE.
- TFE tetrafluoroethylene
- PMVE mole percent perfluoro(methyl vinyl ether)
- iii) 0.3 to 1.5 most preferably 0.5 to 1.0
- Perfluoroelastomers employed in this invention may be manufactured by such well-known processes as those described in Breazeale (U.S. Patent No. 4,281 ,092) or Coughlin et. al. (U.S. Patent No. 5,789,489).
- Bis(aminophenols) which may be employed as curatives in the compositions of this invention include those of the formula
- A is S0 2 , O, CO, alkyl of 1-6 carbon atoms, perfluoroalkyl of 1-10 carbon atoms, or a carbon-carbon bond linking the two aromatic rings.
- the amino and hydroxyl groups are interchangeably in the meta and para positions with respect to the group A.
- the curing agent is a compound selected from the group consisting of 2,2-bis[3-amino-4- hydroxyphenyl]hexafluoropropane (diaminobisphenol AF or DABPAF).
- the hydroxyl groups may be replaced by thiol groups.
- the curing agents can be prepared as disclosed in U.S. Patent Number
- Diaminobisphenol AF can be prepared by nitration of 4,4'-[2,2,2-trifluoro-1 -(trifluoromethyl)ethylidene]bisphenol (i.e. bisphenol AF), preferably with potassium nitrate and trifluoroacetic acid, followed by catalytic hydrogenation, preferably with ethanol as a solvent and a catalytic amount of palladium on carbon as catalyst.
- bis(aminophenol) or bis(aminothiophenol) is typically at a level between 0.2 and 7 (preferably 1 to 2) phr (i.e. parts by weight per hundred parts by weight perfluoroelastomer).
- Ammonia-generating compounds that may be employed in the compositions of this invention are those that are capable of generating ammonia at temperatures of 40°C - 330°C, preferably between 90°C - 220°C.
- Illustrative examples of these compounds include aldehyde ammonia condensation products, including acetaldehyde ammonia; and other compounds, such as hexamethylenetetramine; carbamates, for example t-butyl carbamate, benzyl carbamate, and HCF 2 CF 2 CH(CH 3 )OCONH2; urea; urea hydrochloride; thiourea; amides, such as phthalamide; metal ammine complexes, such as tetraamine copper (ll)sulfate hydrate; ammonia-Lewis acid adducts; carboxamides, such as oxamic acid; biuret; unsubstituted amidines, such as formamidine, formamidine hydrochloride,
- the level of ammonia generating compound is generally from 0.05 to 5 phr, preferably 0.1-1 phr.
- the compositions of the present invention also contain 1 to 25 (preferably 3 to 15) phr hydrophobic silica.
- the average primary particle size of the silicas employed in the compositions of this invention is less than 100 nm, preferably 7 to 16 nm.
- hydrophobic silica is meant silica that is not wetted by water. The number of silanol groups normally present on the surface of hydrophilic silica particles is greatly reduced on the surface of hydrophobic silica.
- Hydrophobic silica is typically made from hydrophilic silica by reaction of the surface silanol groups with an organosilane having between 1 and 3 alkyl groups and between 3 and 1 alkoxy or halogen groups, respectively.
- the alkyl groups do not contain any functional groups such as epoxy, amino, mercapto, vinyl or halogen groups.
- Examples of such silanes include, but are not limited to trimethoxymethylsilane, dimethyldichlorosilane, trimethylchlorosilane, octyltrichlorosilane, etc.
- hydrophobic silicas include, but are not limited to those having on their surface -O 2 -Si-(CH 3 ) 2 , -0-Si-(CH 3 ) 3 , or -0 3 -Si-C 8 H ⁇ 7 groups.
- Commercially hydrophobic silicas include Aerosil ® R972, R974, R812 and R805 (Degussa Aktiengesellschaft, Frankfurt, Germany).
- an organosilane described above may be added to a perfluoroelastomer composition that contains a hydrophilic silica filler.
- hydrophobic inorganic filler such as hydrophobic TiO 2 or hydrophobic alumina may be used in addition to hydrophobic silica in the compositions of this invention.
- These hydrophobic fillers are made by reaction of the surface hydroxyl groups on the corresponding hydrophilic filler with an organosilane of the type described above.
- an organosilane as described above may be added to a perfluoroelastomer composition that contains a hydrophilic inorganic filler such as TiO 2 or alumina.
- hydrophobic silica works better than hydrophilic silica of similar particle size and structure in the compositions of the invention to produce cured articles having good (i.e. low) compression set.
- Additives such as stabilizers, plasticizers, lubricants, other fillers, and processing aids typically utilized in perfluoroelastomer compounding can be incorporated into the compositions of the present invention, provided they have adequate stability for the intended service conditions. In particular, low temperature performance can be enhanced by incorporation of perfluoropolyethers.
- the curable compositions of the present invention are useful in production of gaskets, tubing, and seals. Such articles are generally produced by molding a compounded formulation of the curable composition with various additives under pressure, curing the part, and then subjecting it to a post cure cycle. The cured compositions have excellent physical properties, including compressions set.
- Test specimens were prepared from elastomer compounded with appropriate additives, as described in the formulations listed in the Examples below. Compounding was carried out on a rubber mill. The milled composition was formed into a sheet and a sample was died out into a disk to form the test specimen. Cure characteristics were determined by placing a test specimen in the sealed test cavity of the instrument which was maintained under a positive pressure and elevated temperature. A biconical disk was embedded in the test specimen and was oscillated through an arc of 0.5° at the specified frequency, thereby exerting a shear strain on the test specimen. The force at maximum amplitude (torque) required to rotate the disk is proportional to the stiffness (shear modulus) of the rubber. This torque was recorded as a function of time. Because stiffness of a rubber specimen increases during curing, the test provides a measure of curability. A test is completed when a predetermined time has elapsed. The time required to obtain a curve is a function of the test temperature and the characteristics of the rubber compound.
- FFKM A - A terpolymer containing 68.2 mole percent units of TFE, 31.0 mole percent units of PMVE and 0.80 mole percent units of 8-CNVE was prepared according to the general process described in U.S. Patent No. 5,789,489.
- Control Examples 1-3 Control compositions of peroxide curable perfluoroelastomer compositions containing various types of silicas were mixed on a 16-inch mill. The formulations are shown in Table I. Curing characteristics were measured at 177°C for 15 minutes. O- rings were molded at 177°C for 6 minutes and then post cured in an air oven at 232°C for 6 hours. Tensile properties and compression set of o- rings were then measured according to the Test Methods. The results are shown in Table I. For these peroxide cured control compositions, compression set values were not improved by employing hydrophobic silica in place of hydrophilic silica.
- Example 2 TABLE I Formulation (phr) Control Control Control Example 1
- Example 2 Example 3 FFKM A 100 100 100 Aerosil® 200 VS 1 10 0 0 Aerosil® R972 2 0 10 0 Aerosil® 812 3 0 0 10 Coagent 4 1.5 1.5 1.5 Peroxide 5 3 3 3
- Examples 1-4 and Comparative Examples A and B Test specimens were formulated according to the recipes shown in Table II. Cure characteristics were measured by MDR at 199°C for 30 minutes. Tensile properties and compression set were tested on K214 O-rings that had been molded at 199°C for 5 minutes longer than the T90 determined by MDR. The o-rings were then post cured in nitrogen at 305° for 26 hours (temperature was ramped slowly from room temperature to 305°C). The results are also shown in Table II. The compositions of this invention (i.e. Examples 1 to 4) containing hydrophobic silica had much better (i.e. lower) compression set values than similar compositions (Comparative Examples A and B) that contained hydrophilic silica.
- compositions of the invention containing hydrophobic silica also had better curing characteristics than the comparative compositions containing hydrophilic silica.
- the MDR curves of the comparative compositions showed reversion (i.e. decreasing torque, indicative of lowering of cure state, after MH was reached), whereas MDR curves of the compositions of the invention did not show reversion.
- Aerosil® 200 VS 2 0 0 0 10 0 10
- DABPAF 3 175 175 1.75 175 0 0
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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)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
Claims
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP04781035A EP1654311B1 (en) | 2003-08-15 | 2004-08-13 | Curable perfluoroelastomer composition |
JP2006523940A JP4522998B2 (en) | 2003-08-15 | 2004-08-13 | Curable perfluoroelastomer composition |
DE602004007143T DE602004007143T2 (en) | 2003-08-15 | 2004-08-13 | HARDENABLE PERFLUORELASTOMER COMPOSITIONS |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US49561303P | 2003-08-15 | 2003-08-15 | |
US60/495,613 | 2003-08-15 | ||
US10/863,037 US6992143B2 (en) | 2003-08-15 | 2004-06-08 | Curable perfluoroelastomer composition |
US10/863,037 | 2004-06-08 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2005017017A1 true WO2005017017A1 (en) | 2005-02-24 |
Family
ID=34139032
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2004/026285 WO2005017017A1 (en) | 2003-08-15 | 2004-08-13 | Curable perfluoroelastomer composition |
Country Status (6)
Country | Link |
---|---|
US (1) | US6992143B2 (en) |
EP (1) | EP1654311B1 (en) |
JP (1) | JP4522998B2 (en) |
KR (1) | KR101027257B1 (en) |
DE (1) | DE602004007143T2 (en) |
WO (1) | WO2005017017A1 (en) |
Cited By (7)
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JP2006316112A (en) * | 2005-05-10 | 2006-11-24 | Daikin Ind Ltd | Fluorine-containing elastomer composition and molded article comprising the same |
US8507029B2 (en) | 2007-02-16 | 2013-08-13 | Madico, Inc. | Backing sheet for photovoltaic modules |
US9735298B2 (en) | 2007-02-16 | 2017-08-15 | Madico, Inc. | Backing sheet for photovoltaic modules |
WO2019078238A1 (en) | 2017-10-18 | 2019-04-25 | ダイキン工業株式会社 | Crosslinkable elastomer composition and fluororubber molded article |
US11781004B2 (en) | 2019-11-04 | 2023-10-10 | 3M Innovative Properties Company | Electronic telecommunications articles comprising crosslinked fluoropolymers and methods |
US11866602B2 (en) | 2018-06-12 | 2024-01-09 | 3M Innovative Properties Company | Fluoropolymer compositions comprising fluorinated additives, coated substrates and methods |
US12018144B2 (en) | 2018-06-12 | 2024-06-25 | 3M Innovative Properties Company | Fluoropolymer coating compositions comprising amine curing agents, coated substrates and related methods |
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US7488781B2 (en) * | 2005-05-25 | 2009-02-10 | Gore Enterprise Holdings, Inc. | High purity transparent perfluoroelastomer parts and a process to produce the same |
US20060270780A1 (en) * | 2005-05-25 | 2006-11-30 | Ping Xu | High purity perfluoroelastomer composites and a processes to produce the same |
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US7381774B2 (en) * | 2005-10-25 | 2008-06-03 | Dupont Performance Elastomers, Llc | Perfluoroelastomer compositions for low temperature applications |
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JP5250926B2 (en) * | 1999-06-21 | 2013-07-31 | ダイキン工業株式会社 | Crosslinkable elastomer composition and molded article produced from the composition |
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- 2004-06-08 US US10/863,037 patent/US6992143B2/en not_active Expired - Lifetime
- 2004-08-13 KR KR1020067002217A patent/KR101027257B1/en active IP Right Grant
- 2004-08-13 DE DE602004007143T patent/DE602004007143T2/en not_active Expired - Lifetime
- 2004-08-13 WO PCT/US2004/026285 patent/WO2005017017A1/en active IP Right Grant
- 2004-08-13 JP JP2006523940A patent/JP4522998B2/en not_active Expired - Lifetime
- 2004-08-13 EP EP04781035A patent/EP1654311B1/en not_active Expired - Lifetime
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EP0636663A2 (en) * | 1993-07-28 | 1995-02-01 | Dow Corning Toray Silicone Company, Limited | Blends of fluoroorganic and organosiloxane rubbers |
EP0656391A2 (en) * | 1993-11-30 | 1995-06-07 | Dow Corning Toray Silicone Company, Limited | Rubber composition |
US6281296B1 (en) * | 1998-08-10 | 2001-08-28 | Dupont Dow Elastomers L.L.C. | Curable perfluoroelastomer composition |
Cited By (10)
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JP2006316112A (en) * | 2005-05-10 | 2006-11-24 | Daikin Ind Ltd | Fluorine-containing elastomer composition and molded article comprising the same |
US8507029B2 (en) | 2007-02-16 | 2013-08-13 | Madico, Inc. | Backing sheet for photovoltaic modules |
US9735298B2 (en) | 2007-02-16 | 2017-08-15 | Madico, Inc. | Backing sheet for photovoltaic modules |
WO2019078238A1 (en) | 2017-10-18 | 2019-04-25 | ダイキン工業株式会社 | Crosslinkable elastomer composition and fluororubber molded article |
KR20200042920A (en) | 2017-10-18 | 2020-04-24 | 다이킨 고교 가부시키가이샤 | Crosslinkable elastomer composition and fluorine rubber molded article |
US11753523B2 (en) | 2017-10-18 | 2023-09-12 | Daikin Industries, Ltd. | Crosslinkable elastomer composition and fluororubber molded article |
EP4407002A1 (en) | 2017-10-18 | 2024-07-31 | Daikin Industries, Ltd. | Crosslinkable elastomer composition and fluorororubber molded article |
US11866602B2 (en) | 2018-06-12 | 2024-01-09 | 3M Innovative Properties Company | Fluoropolymer compositions comprising fluorinated additives, coated substrates and methods |
US12018144B2 (en) | 2018-06-12 | 2024-06-25 | 3M Innovative Properties Company | Fluoropolymer coating compositions comprising amine curing agents, coated substrates and related methods |
US11781004B2 (en) | 2019-11-04 | 2023-10-10 | 3M Innovative Properties Company | Electronic telecommunications articles comprising crosslinked fluoropolymers and methods |
Also Published As
Publication number | Publication date |
---|---|
KR101027257B1 (en) | 2011-04-06 |
US6992143B2 (en) | 2006-01-31 |
JP2007502890A (en) | 2007-02-15 |
DE602004007143D1 (en) | 2007-08-02 |
KR20060083409A (en) | 2006-07-20 |
US20050038165A1 (en) | 2005-02-17 |
JP4522998B2 (en) | 2010-08-11 |
EP1654311B1 (en) | 2007-06-20 |
EP1654311A1 (en) | 2006-05-10 |
DE602004007143T2 (en) | 2008-02-21 |
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