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WO2001027194A1 - Compositions fluoroelastomeres et articles fabriques a partir desdites compositions - Google Patents

Compositions fluoroelastomeres et articles fabriques a partir desdites compositions Download PDF

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Publication number
WO2001027194A1
WO2001027194A1 PCT/US2000/003205 US0003205W WO0127194A1 WO 2001027194 A1 WO2001027194 A1 WO 2001027194A1 US 0003205 W US0003205 W US 0003205W WO 0127194 A1 WO0127194 A1 WO 0127194A1
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WO
WIPO (PCT)
Prior art keywords
perfluoro
fluoroelastomer
ammonia
composition
vinyl
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.)
Ceased
Application number
PCT/US2000/003205
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English (en)
Inventor
Werner M. A. Grootaert
George H. Millet
Robert E. Kolb
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Dyneon LLC
Original Assignee
Dyneon LLC
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 Dyneon LLC filed Critical Dyneon LLC
Priority to AU32249/00A priority Critical patent/AU3224900A/en
Publication of WO2001027194A1 publication Critical patent/WO2001027194A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/17—Amines; Quaternary ammonium compounds

Definitions

  • This invention relates to fluoroelastomer compositions having nitrile group- containing cure site monomers
  • the invention relates to articles, including molded articles such as o-rings, seals and gaskets, made from curable fluoroelastomer compositions.
  • Fluoroelastomers i.e., elastomeric fluoropolymers
  • elastomeric fluoropolymers are polymeric materials that exhibit significant tolerance to high temperatures and harsh chemical environments
  • fluoroelastomers are particularly well adapted for use as seals and gaskets and other molded elastomeric parts in systems that are exposed to elevated temperatures and/or corrosive chemicals
  • Such parts are widely used in the chemical processing, semiconductor, aerospace and petroleum industries, among many others
  • Perfluorinated monomers such as tetrafluoroethylene, hexafluoropropene, and perfluorovinyl ethers are among such fluorinated monomer units
  • the polymers typically are cross-linked, i.e., they are vulcanized To accomplish this, a small percentage of a cure site monomer is copolymerized with perfluorinated monomer units
  • Many cure site monomers are known, including those with
  • Such cure site monomers when combined with a peroxide and a coagent, will provide a suitably cured composition
  • One class of curable fluoroelastomers are cured using nitrile group-containing cure site monomers These fluoroelastomers can be cured through a trimerization of the nitrile groups to form thermally stable triazine cross-links
  • the triazine cross-links are formed during a curing process using a catalyst
  • the most useful catalysts for such a cure are organotin compounds Organotin compounds are, however, highly toxic and can leave extractable metallic residues in the finished cured products into which they are incorporated There is therefoie a des ⁇ e to eliminate or substantially reduce their use in commercial curing processes
  • the present invention does this by eliminating the need for organotin compounds in the catalyst system of the curable fluoroelastomer composition
  • the fluoroelastomer compositions of the present invention employ at least one ammonia-generating compound as a catalyst to cure fluoroelastomers incorporating a nitrile group-containing cure site monomei These compounds when subjected to the conditions of curing, provide a source of ammonia that cures the fluoroelastomers without the need of a toxic, organotin catalyst
  • the invention pi ovides a curable fluoroelastomer composition comprising
  • a fluoroelastomer comprising interpolymerized units de ⁇ ved from (a) at least one perfluoroolefin, (b) at least one perfluorovinyl ether selected from the group consisting of perfluoro(alkyl vinyl) ethei s, perfluoro(alkoxy vinyl) ethers, and mixtures thereof, and (c) a cure site component comprising at least one mtnle group, and
  • the invention provides molded articles, including O- ⁇ ngs, gaskets and seals, made from the above curable fluoroelastomer compositions
  • the invention provides cured articles made from the curable compositions These compositions are free from extractable metals such as tin Also, the present invention provides a method for providing a curable fluoroelastomer composition free from extractable tin compounds and a method of stabilizing a curable fluoroelastomer composition against extraction of oiganometals such as tin
  • compositions of the invention retain the advantages of the use of nitrile group- containing cure site monomers That is, they maintain the high temperature performance properties and chemical resistance typically achieved when organotin compounds are used in the catalyst system At the same time, the compositions of the invention eliminate the presence of extractable metal residues resulting from the use of organometal compounds, such as organotin, in the catalyst system
  • compositions of the invention are free of extractable organometal compounds Consequently, they may be characterized as being pure This result is achieved without the need to employ any additional processing steps to eliminate the organometal compounds
  • compositions of the invention are useful in applications where polymer stability is important
  • compositions of the invention are useful where thermal stability and chemical resistance are useful They are also useful in silicon wafer fabrication because they eliminate the source of extractable metallic residues in the composition
  • Fluoroelastomers are polymeric compositions generally formed of interpolymerized units of at least two principal monomers Generally, one of the monomers is a perfluoroolefin and the other is a perfluorovinyl ether, typically either a perfluoro(vinyl alkyl) ether oi a perfluoro(vinyl alkoxy) ether Representative of the perfluoroolefin monomers are tetrafluoroethylene and hexafluoropropene
  • Suitable perfluorinated vinyl ethers include those of the formula
  • R'f and R"f are the same or are different linear or branched perfluoroalkylene groups of 1-6 carbon atoms, a and b are, independently, 0 or an integer from 1 to 10, and Rf is a perfluoroalkyl group of 1 -6 carbon atoms
  • a preferred class of perfluoro(alkyl vinyl) ethers includes compositions of the formula
  • CF 2 CFO(CF 2 CFXO) ⁇ R r (2) where.
  • X is F or CF3 n is 0-5, and Rf is a perfluoroalkyl group of 1 -6 carbon atoms
  • perfluoro(alkyl vinyl) ethers are those where, in reference to either
  • n is 0 or 1 and Rf contains 1 -3 carbon atoms
  • perfluorinated ethers include perfluoro(methyl vinyl) ether, perfluoro(ethyl vinyl) ether, and perfluoro(propyl vinyl) ether
  • CF 2 CFO[(CF 2 ) m (CFZ) u O] n R f (3) where Rf is a perfluoroalkyl group having 1 -6 carbon atoms, m is 0-2, u is 0 or 1, n is 0-5,
  • Z is F or CF3 Preferred members of this class are those in which Rf is C3F7, m is 0, and n is 1
  • CF 2 CFO[(CF 2 CF(CF 3 )O) g (CF 2 ) k O(CF 2 ) p ]C x F 2x+ i (4)
  • Preferred members of this class include compounds where n is 0 or 1 , m is 0 or 1, and x is 1
  • Perfluoro(alkoxy vinyl) ethers useful in the invention include those of the formula
  • CF 2 CFOCF 2 CF(CF 3 )O(CF 2 O) d C e F 2e+ , (5)
  • e is 1-5, preferably 1, and d is 1 -3
  • CF 2 CFO(CF 2 ) 3 OCF 3
  • CF 2 CFOCF 2 CF 2 OCF 3
  • fluorinated copolymers are composed of tetrafluoroethylene and at least one perfluoro(alkyl vinyl) ether as principal monomer units
  • the copolymerized perfluorinated ether units constitute from about 15 to about 50 mole percent of total monomer units present in the polymer
  • the fluorinated monomers of the invention may be polymerized by methods known in the art. For example, the polymerization process can be carried out by free- radical polymerization of the monomers alone or as solutions, emulsions, or dispersions in an organic solvent or water.
  • Emulsion or suspension polymerization typically involves polymerizing monomers in an aqueous medium in the presence of an inorganic free-radical initiator system, such as ammonium persulfate or potassium permanganate, and surfactant or suspending agent
  • Aqueous emulsion polymerization can be carried out continuously under steady- state conditions in which, for example, monomers, water, surfactants, buffers and catalysts are fed continuously to a stirred reactoi under optimum pressure and temperature conditions while the resulting emulsion or suspension is removed continuously.
  • An alternative technique is batch or semibatch polymerization by feeding the ingredients into a stirred reactor and allowing them to react at a set temperature for a specified length of time or by charging ingredients into the reactor and feeding the monomer into the reactor to maintain a constant pressure until a desired amount of polymer is formed
  • the free-radical polymerization process can also be carried out in the presence of a perfluorosulfinate and an oxidizing agent to improve the processability of the resulting perfluoroelastomer composition
  • oxidizing agents are water soluble and capable of converting the sulfinate to a sulfonyl moiety
  • the produced sulfonyl radical is believed to eliminate SO and form a fluorinated radical that initiates the polymerization of the ethylenically unsaturated monomers
  • a number of useful oxidizing agents are known as taught in U.S Patent 5,285,002 and U S Patent 5,639,837 Representative examples of such useful oxidizing agents are sodium, potassium, and ammonium persulfates, perphosphates, perborates, percarbonates, bromates, chlorates and hypochlorites
  • Other useful oxidizing agents include cerium IV compounds such as (NH 4 ) 2 Ce(NO ) 6 .
  • the amount of oxidizing agent used can vary depending
  • Perfluorosulfinates useful for this purpose include those described in U S Patent No 5,285,002 and represented by the general formula
  • R f represents a monovalent fluoroaliphatic radical having, for example, from 1 to
  • R f represents a polyvalent, preferably divalent, fluoroaliphatic radical having, for example, from 1 to 20 carbon atoms, preferably from 2 to 10 carbon atoms
  • M represents a hydrogen atom or cation with valence x, which is 1 or 2
  • j is 1 to 4, preferably 1 or 2
  • the amount of fluoroaliphatic sulfinate employed in the polymerization process can vary, depending, for example, on the molecular weight of polymer desired
  • the amount of fluoroaliphatic sulfinate is from 0 01 to 50 mole percent, and most preferably from 0 05 to 10 mole percent, of sulfinate compound based on total quantity of monomers
  • reducing agents such as sodium, potassium or ammonium sulfites, bisulfite, metabisulfite, hyposulfite, thiosulfite, phosphite, sodium or potassium formaldehyde sulfoxylate or hypophosphite
  • Activators such as ferrous, cuprous, and silver salts, may also be present
  • the cure site component employed in the invention is capable of curing the fluoroelastomer
  • the cure site component generally will comprise at least one nitrile group-containing cure site monomer
  • the cure site component can be partially or fully fluorinated It will be understood that when the cure site component is fully fluorinated, the resulting polymer will be perfluorinated, and that when the cure site component is partially fluorinated, the resulting polymer will still be highly fluorinated
  • Useful nitrile group-containing cure site monomers include nitrile-containing fluorinated olefins and nitrile-containing fluorinated vinyl ethers, such as depicted below
  • CF 2 CF[OCF 2 CF(CF 3 )],0(CF 2 ) 1 CN (10)
  • ammonia-generating compounds include compounds that are solid or liquid at ambient conditions but that generate ammonia under conditions of cure Such compounds include, for example, hexamethylene tetramine (urotropin), dicyan diamid, and metal-containmg compounds of the formula
  • ammonia-generating compounds are substituted and unsubstituted triazine derivatives such as those of the formula wherein R is a hydrogen or a substituted or unsubstituted alkyl, aryl, or aralkyl group having from 1 to about 20 carbon atoms
  • Specific useful triazine derivatives include hexahydro- l ,3,5-.v-triazine and acetaldehyde ammonia trimer
  • the fluoroelastomer compositions of the invention can be cured using one or more peroxide curatives along with the ammonia generating catalysts Suitable peroxide curatives generally are those which generate free radicals at curing temperatures.
  • the curable fluoroelastomer compositions can include any of the adjuvants commonly employed in curable fluoroelastomer formulations
  • one material often blended with a fluoroelastomer composition as a part of the curative system is a coagent (sometimes also referred to as a co-curative) composed of a polyunsaturated compound that is capable of cooperating with the peroxide to provide a useful cure
  • coagents can generally be added in an amount equal to between 0 1 and 10 parts per hundred parts fluoroelastomer, preferably between 1 and 5 parts per hundred parts fluoroelastomer
  • useful coagents include triallyl cyanurate, triallyl isocyanurate, tri(methylallyl isocyanurate, tris(diallylamine)-.v-triazine, triallyl phosphite, N,N-diallyl acrylamide, hexaallyl phosphoramide, N,N,N',N'-t
  • Additives such as carbon black, stabilizers, plasticizers, lubricants, fillers, and processing aids typically utilized in fluoroelastomer compounding can be incorporated into the compositions of the invention, provided they have adequate stability for the intended service conditions In particular, low temperature performance can be enhanced by incorporation of perfluoropolyethers See, for example, U S Pat No 5,268,405
  • Carbon black fillers are typically also employed in elastomers as a means to balance modulus, tensile strength, elongation, hardness, abrasion resistance, conductivity, and processability of the compositions Suitable examples include MT blacks (medium thermal black) designated N-991 , N-990, N-908, and N-907, and large particle size furnace blacks. When used, 1-70 phr of large size particle black is generally sufficient.
  • Fluoropolymer fillers may also be present in the compositions of the invention. Generally, from 1 to 50 parts per hundred fluoroelastomer of a fluoropolymer filler is used. The fluoropolymer filler can be finely divided and easily dispersed as a solid at the highest temperature utilized in fabrication and curing of the fluoroelastomer composition.
  • micropowders are ordinarily partially crystalline polymers
  • useful micropowders include low molecular weight PTFE, PFA, FEP and the like
  • acid acceptors can also be added to the formulations of the invention, though, where the presence of extractable metallic compounds is undesirable (such as for semiconductor applications) the use of inorganic acid acceptors should be minimized, and preferably avoided altogether
  • Commonly used acid acceptors include, for example, zinc oxide, calcium hydroxide, calcium carbonate, magnesium oxide, etc These compounds generally are used in the fluoroelastomer formulation to bind any HF or other acids that might be generated at the high temperatures where fluoroelastomers must function
  • the curable fluoroelastomer compositions of the invention may also be combined with other peroxide curable fluoroelastomer compositions
  • These other peroxide curable fluoroelastomer compositions typically employ small amounts of cure site monomers as a comonomer
  • Suitable cure site monomers are those which, when combined with a peroxide and, preferably a coagent, will provide a cured composition
  • these cure site monomers include at least one halo group (e g , a bromo or an iodo group)
  • the curable compositions of the invention can be prepared by mixing the fluoroelastomer, the peroxide curative, the catalyst, the selected additive or additives, and the other adjuvants, if any, in conventional rubber processing equipment
  • the desired amounts of compounding ingredients and other conventional adjuvants or ingredients can be added to the unvulcanized fluorocarbon gum stock and intimately admixed or compounded therewith by employing any of the usual rubber mixing devices such as internal mixers, (e.g., Banbury mixers), roll mills, or any other convenient mixing device.
  • the temperature of the mixture during the mixing process typically should not rise above about 120°C.
  • the mixture is then processed and shaped, for example, by extrusion (for example, in the shape of a hose or hose lining) or molding (for example, in the form of an O-ring seal).
  • the shaped article can then be heated to cure the gum composition and form a cured elastomer article.
  • Pressing of the compounded mixture usually is conducted at a temperature between about 95°C and about 230°C, preferably between about 150°C and about 205°C, for a period of from 1 minute to 15 hours, typically from 5 minutes to 30 minutes.
  • a pressure of between about 700 kPa and about 20,600 kPa is usually imposed on the compounded mixture in the mold.
  • the molds first may be coated with a release agent and prebaked.
  • the molded vulcanizate is then usually post-cured (e.g., oven-cured) at a temperature usually between about 150°C and about 300°C, typically at about 232°C, for a period of from about 2 hours to 50 hours or more depending on the cross-sectional thickness of the article
  • the temperature during the post cure is usually raised gradually from the lower limit of the range to the desired maximum temperature.
  • the maximum temperature used is preferably about 300°C, and is held at this value for about 4 hours or more.
  • the curable compositions of the invention are useful in production of articles such as gaskets, tubing, and seals. Such articles are 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 curable compositions formulated without inorganic acid acceptors are particularly well suited for applications such as seals and gaskets for manufacturing semiconductor devices, and in seals for high temperature automotive uses.
  • 150 x 150 x 2 0 mm sheets were prepared for physical property determination by pressing at about 6 9 Mega Pascals (M Pa) for 10 minutes at 177°C
  • Example 1 A fluoioelastomei was pi epaied which contained 64 7 mole percent tetrafluoroethylene, 34 8 mole pei cenl pei fluoiomethyl vinyl ether, and 0 5 mole percent of a nitrile group-containing cin e site monomei , by aqueous emulsion polymerization
  • the resulting polymer 100 g was compounded with 15 g of MT N990 carbon black, 5 g of zinc oxide, and 1 g of hexamethylene tetramine
  • a sheet of the compounded admixture was pressed for 15 minutes at 177°C and subsequently post-cured under nitrogen using the following six stages of conditions 25-200°C over 6 hours, 200°C for 16 hours, 200-250°C over 2 hours, 250°C for 8 hours, 250-300°C over 2 hours, and 300°C for 18 hours
  • the cured samples were tested according to the indicated Test Methods, giving the following
  • Example 3 a fluoroelastomer of 61 9 mole percent tetrafluoroethylene,
  • Example 1 giving the following properties
  • Example 4 the fluoropolymer of Example 3 ( 100 g) was compounded with. 20 g of MT N990 carbon black and 1 g of acetaldehyde ammonia trimer trihydrate (available commercially from Fluka Chemie AG of Germany)
  • a sheet of the compounded admixture was pressed for 10 minutes at 177°C and subsequently post-cured for 16 hours at 230°C
  • Example 1 A sheet of the compounded admixture was press cured for 30 minutes at 177° C and subsequently post cured under nitrogen as described in Example 1

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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)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

L'invention concerne une composition fluoroélastomère durcissable, comprenant 1) un fluoroélastomère qui renferme des unités interpolymérisées dérivées de a) au moins une perfluorooléfine, b) au moins un éther de perfluorovinyle sélectionné dans le groupe constitué par des éthers perfluoro(alkyl vinyl), des éthers perfluoro(alcoxy vinyl), et des mélanges de ceux-ci, et c) un composant de site de durcissement comprenant au moins un groupe nitrile; et 2) une composition de catalyseur comprenant au moins un composé produisant de l'ammoniac. L'invention concerne également des procédés de durcissement des compositions fluoroélastomères et des articles fabriqués à partir de ces fluoroélastomères.
PCT/US2000/003205 1999-10-08 2000-02-08 Compositions fluoroelastomeres et articles fabriques a partir desdites compositions Ceased WO2001027194A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU32249/00A AU3224900A (en) 1999-10-08 2000-02-08 Fluoroelastomer compositions and articles made therefrom

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US41559699A 1999-10-08 1999-10-08
US09/415,596 1999-10-08

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Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002088248A1 (fr) * 2001-04-24 2002-11-07 3M Innovative Properties Company Compositions de fluoroelastomeres durcissables au peroxyde
US6825300B2 (en) 2002-11-20 2004-11-30 3M Innovative Properties Company Process for making a fluoropolymer having nitrile end groups
US6933357B2 (en) 2000-02-01 2005-08-23 3M Innovative Properties Company Ultra-clean fluoropolymers
US6963013B2 (en) 2000-04-21 2005-11-08 Solvay Solexis Sp.A. Method of making fluorovinyl ethers and polymers obtainable therefrom
US6992143B2 (en) 2003-08-15 2006-01-31 Dupont Dow Elastomers Llc Curable perfluoroelastomer composition
US7160967B2 (en) 2000-04-21 2007-01-09 Solvey Solexis S.P.A. Fluorovinyl ethers and polymers obtainable therefrom
US7381774B2 (en) * 2005-10-25 2008-06-03 Dupont Performance Elastomers, Llc Perfluoroelastomer compositions for low temperature applications
US7534845B2 (en) 2000-04-21 2009-05-19 Solvay Solexis S.P.A. Fluorovinyl ethers and polymers obtainable therefrom
US8318850B2 (en) 2009-02-26 2012-11-27 E I Du Pont De Nemours And Company Cured perfluoroelastomer article
US8637608B2 (en) 2008-08-18 2014-01-28 3M Innovative Properties Company Azide-containing fluoropolymers and their preparation
US9290619B2 (en) 2011-03-04 2016-03-22 3M Innovative Properties Company Triazine containing fluoropolyether elastomers having low glass transition temperature
US9315644B2 (en) 2012-12-03 2016-04-19 E I Du Pont De Nemours And Company Cured perfluoroelastomer article
EP1240125B2 (fr) † 1999-12-22 2016-04-20 3M Innovative Properties Company Vinyl-ethers contenant du fluor
JP2017071763A (ja) * 2015-09-26 2017-04-13 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーＥ．Ｉ．Ｄｕ Ｐｏｎｔ Ｄｅ Ｎｅｍｏｕｒｓ Ａｎｄ Ｃｏｍｐａｎｙ フルオロエラストマー用硬化剤
WO2018078015A1 (fr) * 2016-10-27 2018-05-03 Solvay Specialty Polymers Italy S.P.A. Composition fluoroélastomère
US10023736B2 (en) 2014-02-19 2018-07-17 3M Innovative Properties Company Hybrid fluoroelastomer composition, curable composition, and methods of making and using the same
EP3556803A1 (fr) * 2015-09-26 2019-10-23 E. I. du Pont de Nemours and Company Agent de durcissement pour composes
KR20190130145A (ko) * 2017-03-31 2019-11-21 솔베이 스페셜티 폴리머스 이태리 에스.피.에이. 플루오로엘라스토머 조성물
KR20210099076A (ko) * 2018-12-04 2021-08-11 주식회사 발카 엘라스토머 조성물 및 시일재
WO2024110375A1 (fr) 2022-11-22 2024-05-30 Dupont Specialty Products Operations Sarl Composés perfluoroélastomères
WO2024158733A1 (fr) 2023-01-27 2024-08-02 Dupont Specialty Products Usa, Llc Compositions fluoropolymères et articles fabriqués à partir de celles-ci

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Cited By (36)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1240125B2 (fr) † 1999-12-22 2016-04-20 3M Innovative Properties Company Vinyl-ethers contenant du fluor
US6933357B2 (en) 2000-02-01 2005-08-23 3M Innovative Properties Company Ultra-clean fluoropolymers
US6593416B2 (en) 2000-02-01 2003-07-15 3M Innovative Properties Company Fluoropolymers
US7534845B2 (en) 2000-04-21 2009-05-19 Solvay Solexis S.P.A. Fluorovinyl ethers and polymers obtainable therefrom
US7160967B2 (en) 2000-04-21 2007-01-09 Solvey Solexis S.P.A. Fluorovinyl ethers and polymers obtainable therefrom
US6963013B2 (en) 2000-04-21 2005-11-08 Solvay Solexis Sp.A. Method of making fluorovinyl ethers and polymers obtainable therefrom
WO2002088248A1 (fr) * 2001-04-24 2002-11-07 3M Innovative Properties Company Compositions de fluoroelastomeres durcissables au peroxyde
US6825300B2 (en) 2002-11-20 2004-11-30 3M Innovative Properties Company Process for making a fluoropolymer having nitrile end groups
US6992143B2 (en) 2003-08-15 2006-01-31 Dupont Dow Elastomers Llc Curable perfluoroelastomer composition
US7381774B2 (en) * 2005-10-25 2008-06-03 Dupont Performance Elastomers, Llc Perfluoroelastomer compositions for low temperature applications
US8637608B2 (en) 2008-08-18 2014-01-28 3M Innovative Properties Company Azide-containing fluoropolymers and their preparation
US9388257B2 (en) 2008-08-18 2016-07-12 3M Innovative Properties Company Azide-containing fluoropolymers and their preparation
US9828446B2 (en) 2008-08-18 2017-11-28 3M Innovative Properties Company Azide-containing fluoropolymers and their preparation
US8318850B2 (en) 2009-02-26 2012-11-27 E I Du Pont De Nemours And Company Cured perfluoroelastomer article
US9290619B2 (en) 2011-03-04 2016-03-22 3M Innovative Properties Company Triazine containing fluoropolyether elastomers having low glass transition temperature
US9315644B2 (en) 2012-12-03 2016-04-19 E I Du Pont De Nemours And Company Cured perfluoroelastomer article
US10023736B2 (en) 2014-02-19 2018-07-17 3M Innovative Properties Company Hybrid fluoroelastomer composition, curable composition, and methods of making and using the same
US9908992B2 (en) 2015-09-26 2018-03-06 E I Du Pont De Nemours And Company Curing agents for fluoroelastomers
EP3556803A1 (fr) * 2015-09-26 2019-10-23 E. I. du Pont de Nemours and Company Agent de durcissement pour composes
EP3205690A1 (fr) * 2015-09-26 2017-08-16 E. I. du Pont de Nemours and Company Agents de durcissement pour fluoroélastomères
JP2017071763A (ja) * 2015-09-26 2017-04-13 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーＥ．Ｉ．Ｄｕ Ｐｏｎｔ Ｄｅ Ｎｅｍｏｕｒｓ Ａｎｄ Ｃｏｍｐａｎｙ フルオロエラストマー用硬化剤
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