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US20070015865A1 - Aqueous emulsion polymerization of fluorinated monomers using a perfluoropolyether surfactant - Google Patents

Aqueous emulsion polymerization of fluorinated monomers using a perfluoropolyether surfactant Download PDF

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Publication number
US20070015865A1
US20070015865A1 US11/457,500 US45750006A US2007015865A1 US 20070015865 A1 US20070015865 A1 US 20070015865A1 US 45750006 A US45750006 A US 45750006A US 2007015865 A1 US2007015865 A1 US 2007015865A1
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perfluoropolyether
fluorinated
dispersion
polymerization
emulsion polymerization
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Klaus Hintzer
Michael Jurgens
Harald Kaspar
Kai Lochhaas
Andreas Maurer
Tilman Zipplies
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3M Innovative Properties Co
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3M Innovative Properties Co
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Assigned to 3M INNOVATIVE PROPERTIES COMPANY reassignment 3M INNOVATIVE PROPERTIES COMPANY ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: KASPAR, HARALD, ZIPPLIES, TILMAN, JURGENS, MICHAEL, LOCHHAAS, KAI HELMUT, MAURER, ANDREAS R., HINTZER, KLAUS
Publication of US20070015865A1 publication Critical patent/US20070015865A1/en
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    • 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

Definitions

  • the present invention relates to the aqueous emulsion polymerization of fluorinated monomers to produce fluoropolymers.
  • Fluoropolymers i.e. polymers having a fluorinated backbone
  • Fluoropolymers have been long known and have been used in a variety of applications because of several desirable properties such as heat resistance, chemical resistance, weatherability, UV-stability etc.
  • the various fluoropolymers are for example described in “Modern Fluoropolymers”, edited by John Scheirs, Wiley Science 1997.
  • fluoropolymers include polytetrafluoroethylene (PTFE), copolymers of tetrafluoroethylene (TFE) and hexafluoropropylene (HFP) (FEP polymers), perfluoroalkoxy copolymers (PFA), ethylene-tetrafluoroethylene (ETFE) copolymers, terpolymers of tetrafluoroethylene, hexafluoropropylene and vinylidene fluoride (THV) and polyvinylidene fluoride polymers (PVDF).
  • PTFE polytetrafluoroethylene
  • TFE tetrafluoroethylene
  • HFP hexafluoropropylene
  • FEP polymers perfluoroalkoxy copolymers
  • ETFE ethylene-tetrafluoroethylene copolymers
  • the most commonly employed polymerization methods include suspension polymerization and especially aqueous emulsion polymerization.
  • the aqueous emulsion polymerization normally involves the polymerization in the presence of a fluorinated surfactant, which is generally used for the stabilization of the polymer particles formed.
  • the suspension polymerization generally does not involve the use of surfactant but results in substantially larger polymer particles than in case of the aqueous emulsion polymerization.
  • the polymer particles in case of suspension polymerization will quickly settle out whereas in case of dispersions obtained in emulsion polymerization generally good stability over a long period of time is obtained.
  • WO 97/17381 discloses an aqueous emulsion polymerization in the absence of a surfactant wherein a radical initiator system of a reducing agent and oxidizing agent is used to initiate the polymerization and whereby the initiator system is added in one or more further charges during the polymerization. So-called emulsifier free polymerization has further been disclosed in WO 02/88206 and WO 02/88203.
  • WO 02/88207 teaches an emulsifier free polymerization using certain chain transfer agents to minimize formation of water soluble fluorinated compounds.
  • An emulsifier free polymerization is further disclosed in RU 2158274 for making an elastomeric copolymer of hexafluoropropylene and vinylidene fluoride.
  • the aqueous emulsion polymerization process in the presence of fluorinated surfactants is still a desirable process to produce fluoropolymers because it can yield stable fluoropolymer particle dispersions in high yield and in a more environmental friendly way than for example polymerizations conducted in an organic solvent.
  • the emulsion polymerization process is carried out using a perfluoroalkanoic acid or salt thereof as a surfactant.
  • surfactants are typically used as they provide a wide variety of desirable properties such as high speed of polymerization, good copolymerization properties of fluorinated olefins with comonomers, small particle sizes of the resulting dispersion can be achieved, good polymerization yields i.e. a high amount of solids can be produced, good dispersion stability, etc.
  • environmental concerns have been raised against these surfactants and moreover these surfactants are generally expensive.
  • surfactants of the general formula R f —C 2 H 4 —SO 3 M, wherein R f represents a perfluorinated aliphatic group and wherein M represents a cation have been disclosed in U.S. Pat. No. 5,789,508, U.S. Pat. No. 4,025,709, U.S. Pat. No. 5,688,884 and U.S. Pat. No. 4,380,618.
  • U.S. Pat. No. 5,763,552 discloses partially fluorinated surfactants of the general formula R f —(CH 2 ) m —R′ f —COOM wherein R f represents a perfluoroalkyl group or a perfluoroalkoxy group of 3 to 8 carbon atoms, R′ f represents a perfluoroalkylene of 1 to 4 carbon atoms and m is 1-3.
  • U.S. Pat. No. 4,621,116 discloses perfluoroalkoxy benzene sulphonic acids and salts thereof in the aqueous emulsion polymerization of fluorinated monomers.
  • U.S. Pat. No. 3,271,341 teaches perfluoropolyethers of the general formula: F—(CF 2 ) m —O—[CFX—CF 2 —O] n —CFX—COOA wherein m is 1 to 5, X is F or CF 3 , A is a monovalent cation and n is 0 to 10.
  • the perfluoropolyethers are taught as emulsifiers in the emulsion polymerization of ethylenically unsaturated monomers.
  • U.S. Publication No. 2005/0090613 discloses fluorinated polyethers of the formula: F—(CF 2 ) m —O—[CFX—CF 2 —O] n —CFX—COOA wherein m is 3 to 10, X is F or a perfluoroalkyl group, n is 0, 1 or 2 and A is the counter ion of the carboxylic anion.
  • These polyethers are taught as emulsifiers in the emulsion polymerization of fluorinated olefins.
  • perfluoropolyethers having neutral end groups in an aqueous emulsion polymerization is disclosed in U.S. Pat. No. 4,864,006, U.S. Pat. No. 4,789,717 and EP 625526.
  • U.S. Pat. No. 4,864,006 and EP 625526 disclose the use of microemulsion prepared from perfluoropolyethers having neutral end groups in an aqueous emulsion polymerization of fluorinated monomers.
  • a certain perfluoropolyether having carboxylic end groups is taught to emulsify the neutral perfluoropolyether.
  • EP 1,334,996 discloses certain perfluoropolyethers having carboxylic acid groups or salts thereof at both end groups, i.e. the perfluoropolyethers are bifunctional.
  • the perfluoropolyethers are taught for use in aqueous dispersions of fluoropolymers and in the preparation of such dispersion by aqueous emulsion polymerization.
  • WO 00/71590 teaches the use of a combination of perfluoropolyether surfactants having a carboxylic acid group or salt thereof with a fluoroalkyl carboxylic acid or sulphonic acid or salt thereof. It is taught that the perfluoropolyether surfactants on their own are not very powerful surfactants.
  • the alternative surfactant or dispersant allows for a high polymerization rate, good dispersion stability, good yields, good copolymerization properties and/or the possibility of obtaining a wide variety of particle sizes including small particle sizes.
  • the properties of the resulting fluoropolymer should generally not be negatively influenced and preferably would be improved.
  • the resulting dispersions have good or excellent properties in coating applications and/or impregnation of substrates, including for example good film forming properties.
  • the polymerization can be carried out in a convenient and cost effective way, preferably using equipment commonly used in the aqueous emulsion polymerization of fluorinated monomers.
  • perfluoropolyethers of the following formula (I) or (II) are effective in the aqueous emulsion polymerization, even when used without the addition of other surfactants such as perfluoroalkanoic acids and salts thereof.
  • the perfluoropolyether surfactants correspond to formula (I) or (II) CF 3 —(OCF 2 ) m —O—CF 2 —X (I) wherein m has a value of 1 to 6 and X represents a carboxylic acid group or salt thereof; CF 3 —O—(CF 2 ) 3 —(OCF(CF 3 )—CF 2 ) z —O-L-Y (II) wherein z has a value of 0, 1, 2 or 3, L represents a divalent linking group selected from —CF(CF 3 )—, —CF 2 — and —CF 2 CF 2 — and Y represents a carboxylic acid group or salt thereof.
  • carboxylic acid salts include sodium, potassium and ammonium (NH 4 ) salts.
  • the invention relates to a method for making a fluoropolymer comprising an aqueous emulsion polymerization of one or more fluorinated monomers wherein said aqueous emulsion polymerization is carried out in the presence of a perfluoropolyether as an emulsifier, said perfluoropolyether being selected from the group consisting of perfluoropolyethers according to above formula (I), perfluoropolyethers according to above formula (II) and mixtures of perfluoropolyethers according to formula (I) and/or (II).
  • the invention relates to an aqueous dispersion of a fluoropolymer comprising a perfluoropolyether as an emulsifier, said perfluoropolyether being selected from the group consisting of perfluoropolyethers according to above formula (I), perfluoropolyethers according to above formula (II) and mixtures of perfluoropolyethers according to formula (I) and/or (II).
  • the present invention relates to an aqueous dispersion of a fluoropolymer comprising a perfluoropolyether selected from the group consisting of perfluoropolyethers according to above formula (I), perfluoropolyethers according to above formula (II) and mixtures of perfluoropolyethers according to formula (I) and/or (II) as an emulsifier and wherein the aqueous dispersion is free of perfluorinated alkanoic acids or salts thereof.
  • a perfluoropolyether selected from the group consisting of perfluoropolyethers according to above formula (I), perfluoropolyethers according to above formula (II) and mixtures of perfluoropolyethers according to formula (I) and/or (II) as an emulsifier and wherein the aqueous dispersion is free of perfluorinated alkanoic acids or salts thereof.
  • the invention in a further aspect relates to aqueous dispersions of a fluoropolymer comprising a perfluoropolyether selected from the group consisting of perfluoropolyethers according to above formula (I), perfluoropolyethers according to above formula (II) and mixtures of perfluoropolyethers according to formula (I) and/or (II) as an emulsifier and additionally comprising a non-ionic surfactant, typically in an amount of 1 to 12% by weight based on the weight of fluoropolymer solids.
  • a perfluoropolyether selected from the group consisting of perfluoropolyethers according to above formula (I), perfluoropolyethers according to above formula (II) and mixtures of perfluoropolyethers according to formula (I) and/or (II) as an emulsifier and additionally comprising a non-ionic surfactant, typically in an amount of 1 to 12% by weight
  • the aqueous emulsion polymerization of fluorinated monomers can be conducted using one or more perfluoropolyethers according to formula (I) and/or (II) as emulsifier.
  • the polymerization may be carried out using a perfluoropolyether or mixture of perfluoropolyethers according to formula (I).
  • a perfluoropolyether or mixture of perfluoropolyethers according to formula (II) is used.
  • a mixture of one or more perfluoropolyethers according to formula (I) and one or more perfluoropolyethers according to formula (II) is used.
  • Perfluoropolyethers of formula (I) are commercially available from Anles Ltd., St. Russia, Russia. These compounds may be prepared for example as described by Ershov and Popova in Fluorine Notes 4(11), 2002. Also, these perfluoropolyethers typically form as byproducts in the manufacturing of hexafluoropropylene oxide by direct oxidation of hexafluoropropylene.
  • Perfluoropolyethers according to formula (II) can be derived from reactants that are also used in the manufacturing of fluorinated vinyl ethers as described in U.S. Pat. No. 6,255,536. Accordingly, these perfluoropolyethers can be obtained in an economically attractive way as they can be derived from other starting products that may be used and needed in the manufacturing of fluoromonomers and fluoropolymers.
  • the perfluoropolyether is used in the aqueous emulsion polymerization of one or more fluorinated monomers, in particular gaseous fluorinated monomers.
  • gaseous fluorinated monomers monomers that are present as a gas under the polymerization conditions.
  • the polymerization of the fluorinated monomers is started in the presence of the perfluoropolyether, i.e. the polymerization is initiated in the presence of the perfluoropolyether.
  • the amount of perfluoropolyether surfactant used may vary depending on desired properties such as amount of solids, particle size etc.
  • the amount of perfluoropolyether surfactant will be between 0.01% by weight based on the weight of water in the polymerization and 5% by weight, for example between 0.05% by weight and 2% by weight. A practical range is between 0.05% by weight and 1% by weight. While the polymerization is generally initiated in the presence of the perfluoropolyether surfactant, it is not excluded to add further perfluoropolyether surfactant during the polymerization although such will generally not be necessary. Nevertheless, it may be desirable to add certain monomer to the polymerization in the form of an aqueous emulsion.
  • fluorinated monomers and in particular perfluorinated co-monomers that are liquid under the polymerization conditions may be advantageously added in the form of an aqueous emulsion.
  • emulsion of such co-monomers is preferably prepared using the perfluoropolyether as an emulsifier.
  • the aqueous emulsion polymerization may be carried out at a temperatures between 10 to 100° C., preferably 30° C. to 80° C. and the pressure is typically between 2 and 30 bar, in particular 5 to 20 bar.
  • the reaction temperature may be varied during the polymerization to influence the molecular weight distribution, i.e., to obtain a broad molecular weight distribution or to obtain a bimodal or multimodal molecular weight distribution.
  • the aqueous emulsion polymerization is typically initiated by an initiator including any of the initiators known for initiating a free radical polymerization of fluorinated monomers.
  • Suitable initiators include peroxides and azo compounds and redox based initiators.
  • Specific examples of peroxide initiators include, hydrogen peroxide, sodium or barium peroxide, diacylperoxides such as diacetylperoxide, disuccinyl peroxide, dipropionylperoxide, dibutyrylperoxide, dibenzoylperoxide, benzoylacetylperoxide, diglutaric acid peroxide and dilaurylperoxide, and further per-acids and salts thereof such as e.g.
  • ammonium, sodium or potassium salts examples include peracetic acid. Esters of the peracid can be used as well and examples thereof include tert.-butylperoxyacetate and tert.-butylperoxypivalate.
  • examples of inorganic include for example ammonium-alkali- or earth alkali salts of persulfates, permanganic or manganic acid or manganic acids.
  • a persulfate initiator e.g. ammonium persulfate (APS), can be used on its own or may be used in combination with a reducing agent.
  • Suitable reducing agents include bisulfites such as for example ammonium bisulfite or sodium metabisulfite, thiosulfates such as for example ammonium, potassium or sodium thiosulfate, hydrazines, azodicarboxylates and azodicarboxyldiamide (ADA).
  • Further reducing agents that may be used include sodium formaldehyde sulfoxylate (Rongalit®) or fluoroalkyl sulfinates as disclosed in U.S. Pat. No. 5,285,002.
  • the reducing agent typically reduces the half-life time of the persulfate initiator.
  • a metal salt catalyst such as for example copper, iron or silver salts may be added.
  • the amount of initiator may be between 0.01% by weight (based on the fluoropolymer solids to be produced) and 1% by weight. In one embodiment, the amount of initiator is between 0.05 and 0.5% by weight. In another embodiment, the amount may be between 0.05 and 0.3% by weight.
  • the aqueous emulsion polymerization system may further comprise other materials, such as buffers and, if desired, complex-formers or chain-transfer agents.
  • chain transfer agents include dimethyl ether, methyl t-butyl ether, alkanes having 1 to 5 carbon atoms such as ethane, propane and n-pentane, halogenated hydrocarbons such as CCl 4 , CHCl 3 and CH 2 Cl 2 and hydrofluorocarbon compounds such as CH 2 F—CF 3 (R134a).
  • fluorinated monomers that may be polymerized using the perfluoropolyether surfactant as an emulsifier include partially or fully fluorinated gaseous monomers including fluorinated olefins such as tetrafluoroethylene, chlorotrifluoroethylene, hexafluoropropylene, vinyl fluoride, vinylidene fluoride, partially or fully fluorinated allyl ethers and partially or fully fluorinated vinyl ethers.
  • the polymerization may further involve non-fluorinated monomers such as ethylene and propylene.
  • fluorinated monomers that may be used in the aqueous emulsion polymerization according to the invention include those corresponding to the formula: CF 2 ⁇ CF—O—R f (III) wherein R f represents a perfluorinated aliphatic group that may contain one or more oxygen atoms.
  • the perfluorovinyl ethers correspond to the general formula: CF 2 ⁇ CFO(R f O) n (R′ f O) m R′′ f (IV) wherein 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.
  • perfluorovinyl ethers examples include perfluoro-2-propoxypropylvinyl ether (PPVE-2), perfluoro-3-methoxy-n-propylvinyl ether, perfluoro-2-methoxy-ethylvinyl ether, perfluoromethylvinyl ether (PMVE), perfluoro-n-propylvinyl ether (PPVE-1) and CF 3 —(CF 2 ) 2 —O—CF(CF 3 )—CF 2 —O—CF(CF 3 )—CF 2 —O—CF ⁇ CF 2 .
  • PPVE-2 perfluoro-2-propoxypropylvinyl ether
  • PMVE perfluoromethylvinyl ether
  • PPVE-1 perfluoro-n-propylvinyl ether
  • the polymerization may involve comonomers that have a functional group such as for example a group capable of participating in a peroxide cure reaction.
  • a functional group such as for example a group capable of participating in a peroxide cure reaction.
  • Such functional groups include halogens such as Br or I as well as nitrile groups.
  • Specific examples of such comonomers that may be listed here include
  • bromo- or iodo-(per)fluoroalkyl-(per)fluorovinylethers having the formula: Z—R f —O—CX ⁇ CX 2 wherein each X may be the same or different and represents H or F, Z is Br or I, R f is a (per)fluoroalkylene C 1 -C 12 , optionally containing chlorine and/or ether oxygen atoms; for example: BrCF 2 —O—CF ⁇ CF 2 , BrCF 2 CF 2 —O—CF ⁇ CF 2 , BrCF 2 CF 2 CF 2 —O—CF ⁇ CF 2 , BrCF 2 CF 2 CF 2 —O—CF ⁇ CF 2 , CF 3 CFBrCF 2 —O—CF ⁇ CF 2 , and the like; and
  • bromo- or iodo containing fluoroolefins such as those having the formula: Z′—(R f ′) r —CX ⁇ CX 2 , wherein each X independently represents H or F, Z′ is Br or I, R f ′ is a perfluoroalkylene C 1 -C 12 , optionally containing chlorine atoms and r is 0 or 1; for instance: bromotrifluoroethylene, 4-bromo-perfluorobutene-1, and the like; or bromofluoroolefins such as 1-bromo-2,2-difluoroethylene and 4-bromo-3,3,4,4-tetrafluorobutene-1.
  • nitrile containing monomers examples include those that correspond to one of the following formulas: CF 2 ⁇ CF—CF 2 —O—R f —CN CF 2 ⁇ CFO(CF 2 ) L CN CF 2 ⁇ CFO [CF 2 CF(CF 3 )O] g (CF 2 ) v OCF(CF 3 )CN CF 2 ⁇ CF [OCF 2 CF(CF 3 )] k O(CF 2 ) u CN wherein L represents an integer of 2 to 12; g represents an integer of 0 to 4; k represents 1 or 2; v represents an integer of 0 to 6; u represents an integer of 1 to 6, R f is a perfluoroalkylene or a bivalent perfluoroether group.
  • nitrile containing liquid fluorinated monomers include perfluoro(8-cyano-5-methyl-3,6-dioxa-1-octene), CF 2 ⁇ CFO(CF 2 ) 5 CN, and CF 2 ⁇ CFO(CF 2 ) 3 OCF(CF 3 )CN.
  • a fluorinated liquid may be added to the polymerization system.
  • liquid is meant that the compound should be liquid at the conditions of temperature and pressure employed in the polymerization process.
  • the fluorinated liquid has a boiling point of at least 50° C., preferably at least 80° C. at atmospheric pressure.
  • Fluorinated liquids include in particular highly fluorinated hydrocarbons as well as liquid fluorinated monomers.
  • highly fluorinated in connection with the present invention is used to indicate compounds in which most and preferably all hydrogen atoms have been replaced with fluorine atoms as well as compounds wherein the majority of hydrogen atoms have been replaced with fluorine atoms and where most or all of the remainder of the hydrogen atoms has been replaced with bromine, chlorine or iodine.
  • a highly fluorinated compound in connection with this invention will have only few, e.g., 1 or 2 hydrogen atoms replaced by a halogen other than fluorine and/or have only one or two hydrogen atoms remaining.
  • the hydrogen atoms When not all hydrogen atoms are replaced by fluorine or another halogen, i.e., the compound is not perfluorinated, the hydrogen atoms should generally be in a position on the compound such that substantially no chain transfer thereto occurs, i.e., such that the compound acts as an inert in the polymerization, i.e., the compound does not participate in the free radical polymerization.
  • Compounds in which all hydrogens have been replaced by fluorine and/or other halogen atoms are herein referred to as ‘perfluorinated’.
  • Liquid and fluorinated hydrocarbon compounds that can be used as fluorinated liquid typically comprise between 3 and 25 carbon atoms, preferably between 5 and 20 carbon atoms and may contain up to 2 heteroatoms selected from oxygen, sulfur or nitrogen.
  • the highly fluorinated hydrocarbon compound is a perfluorinated hydrocarbon compound.
  • Suitable perfluorinated hydrocarbons include perfluorinated saturated linear, branched and/or cyclic aliphatic compounds such as a perfluorinated linear, branched or cyclic alkane; a perfluorinated aromatic compound such as perfluorinated benzene, or perfluorinated tetradecahydro phenanthene.
  • It can also be a perfluorinated alkyl amine such as a perfluorinated trialkyl amine. It can further be a perfluorinated cyclic aliphatic, such as decalin; and preferably a heterocyclic aliphatic compound containing oxygen or sulfur in the ring, such as perfluoro-2-butyl tetrahydrofuran.
  • perfluorinated hydrocarbons include perfluoro-2-butyltetrahydrofuran, perfluorodecalin, perfluoromethyldecalin, perfluoromethylcyclohexane, perfluoro(1,3-dimethylcyclohexane), perfluorodimethyldecahydronaphthalene, perfluorofluorene, perfluoro(tetradecahydrophenanthrene), perfluorotetracosane, perfluorokerosenes, octafluoronaphthalene, oligomers of poly(chlorotrifluoroethylene), perfluoro(trialkylamine) such as perfluoro(tripropylamine), perfluoro(tributylamine), or perfluoro(tripentylamine), and octafluorotoluene, hexafluorobenzene, and commercial fluorinated solvents, such as Fluorinert FC-75,
  • a suitable inert liquid and highly fluorinated hydrocarbon compound is C 3 F 7 —O—CF(CF 3 )—CF 2 —O—CHF—CF 3 .
  • the fluorinated liquid may also comprise liquid fluorinated monomer alone or in combination with above described liquid fluorinated compounds.
  • liquid fluorinated monomers include monomers that are liquid under the polymerization conditions and that are selected from (per)fluorinated vinyl ethers, (per)fluorinated allyl ethers and (per)fluorinated alkyl vinyl monomers.
  • a fluorinated liquid When a fluorinated liquid is used, it will generally be preferred to emulsify the fluorinated liquid.
  • the fluorinated liquid is emulsified using the perfluoropolyether surfactant.
  • a fluorinated liquid when a fluorinated liquid is used in the polymerization, it will be advantageous that at least a portion thereof or all is provided at the start of the polymerization such that the polymerization is initiated in the presence of the emulsified fluorinated liquid.
  • the use of the fluorinated liquid may improve such properties as the rate of polymerization, incorporation of co-monomers and may reduce the particle size and/or improve the amount of solids that can be obtained at the end of the polymerization.
  • the aqueous emulsion polymerization may be used to produce a variety of fluoropolymers including perfluoropolymers, which have a fully fluorinated backbone, as well as partially fluorinated fluoropolymers. Also the aqueous emulsion polymerization may result in melt-processible fluoropolymers as well as those that are not melt-processible such as for example polytetrafluoroethylene and so-called modified polytetrafluoroethylene. The polymerization process can further yield fluoropolymers that can be cured to make fluoroelastomers as well as fluorothermoplasts.
  • Fluorothermoplasts are generally fluoropolymers that have a distinct and well noticeable melting point, typically in the range of 60 to 340° C. or between 100 and 320° C. They thus have a substantial crystalline phase. Fluoropolymers that are used for making fluoroelastomers typically are amorphous and/or have a neglectable amount of crystallinity such that no or hardly any melting point is discernable for these fluoropolymers.
  • the aqueous emulsion polymerization results in a dispersion of the fluoropolymer in water.
  • the amount of solids of the fluoropolymer in the dispersion directly resulting from the polymerization will vary between 3% by weight and about 40% by weight depending on the polymerization conditions. A typical range is between 5 and 30% by weight.
  • the particle size (volume average particle size) of the fluoropolymer is typically between 50 nm and 350 nm with a typical particle size being between 100 nm and about 300 nm.
  • the amount of perfluoropolyether according to formula (I) and/or (II) in the resulting dispersion is typically between 0.001 and 5% by weight based on the amount of fluoropolymer solids in the dispersion.
  • a typical amount may be from 0.01 to 2% by weight or from 0.02 to 1% by weight.
  • the fluoropolymer may be isolated from the dispersion by coagulation if a polymer in solid form is desired. Also, depending on the requirements of the application in which the fluoropolymer is to be used, the fluoropolymer may be post-fluorinated so as to convert any thermally unstable end groups into stable CF 3 end groups.
  • the fluoropolymer may be post-fluorinated as described in for example EP 222945. Generally, the fluoropolymer will be post fluorinated such that the amount of end groups in the fluoropolymer other than CF 3 is less than 80 per million carbon atoms.
  • an aqueous dispersion of the fluoropolymer is desired and hence the fluoropolymer will not need to be separated or coagulated from the dispersion.
  • a fluoropolymer dispersion suitable for use in coating applications such as for example in the impregnation of fabrics or in the coating of metal substrates to make for example cookware, it will generally be desired to add further stabilizing surfactants and/or to further increase the fluoropolymer solids.
  • non-ionic stabilizing surfactants may be added to the fluoropolymer dispersion. Typically these will be added thereto in an amount of 1 to 12% by weight based on fluoropolymer solids.
  • non-ionic surfactants examples include R 1 —O—[CH 2 CH 2 O] n —[R 2 O] m —R 3 (V) wherein R 1 represents an aromatic or aliphatic hydrocarbon group having at least 8 carbon atoms, R 2 represents an alkylene having 3 carbon atoms, R 3 represents hydrogen or a C 1 -C 3 alkyl group, n has a value of 0 to 40, m has a value of 0 to 40 and the sum of n+m being at least 2. It will be understood that in the above formula (V), the units indexed by n and m may appear as blocks or they may be present in an alternating or random configuration.
  • non-ionic surfactants include alkylphenol oxy ethylates such as ethoxylated p-isooctylphenol commercially available under the brand name TRITONTM such as for example TRITONTM X 100 wherein the number of ethoxy units is about 10 or TRITONTM X 114 wherein the number of ethoxy units is about 7 to 8.
  • alkylphenol oxy ethylates such as ethoxylated p-isooctylphenol commercially available under the brand name TRITONTM such as for example TRITONTM X 100 wherein the number of ethoxy units is about 10 or TRITONTM X 114 wherein the number of ethoxy units is about 7 to 8.
  • R 1 n the above formula (V) represents an alkyl group of 4 to 20 carbon atoms
  • m is 0 and R 3 is hydrogen.
  • Non-ionic surfactants according to formula (V) in which the hydrophilic part comprises a block-copolymer of ethoxy groups and propoxy groups may be used as well.
  • Such non-ionic surfactants are commercially available from Clariant GmbH under the trade designation GENAPOL® PF 40 and GENAPOL® PF 80.
  • the amount of fluoropolymer solids in the dispersion may be upconcentrated as needed or desired to an amount between 30 and 70% by weight. Any of the known upconcentration techniques may be used including ultrafiltration and thermal upconcentration.
  • the obtained fluoropolymer may be conveniently used in most applications optionally after the addition of non-ionic surfactant and/or upconcentration and without removing the perfluoropolyether surfactant. Nevertheless, for reasons of for example costs, it may be desirable to remove the perfluoropolyether from the dispersion. It has been found that the perfluoropolyether surfactant can be readily removed from the aqueous dispersion using an anion exchange resin. Accordingly, a non-ionic surfactant, e.g. as disclosed above is added to the fluoropolymer dispersion, generally in an amount of 1 to 12% by weight and the fluoropolymer dispersion is then contacted with an anion exchange resin.
  • a non-ionic surfactant e.g. as disclosed above is added to the fluoropolymer dispersion, generally in an amount of 1 to 12% by weight and the fluoropolymer dispersion is then contacted with an anion exchange resin.
  • the anion exchange process is preferably carried out in essentially basic conditions. Accordingly, the ion exchange resin will preferably be in the OH— form although anions like fluoride or sulfate may be used as well.
  • the specific basicity of the ion exchange resin is not very critical. Strongly basic resins are preferred because of their higher efficiency.
  • the process may be carried out by feeding the fluoropolymer dispersion through a column that contains the ion exchange resin or alternatively, the fluoropolymer dispersion may be stirred with the ion exchange resin and the fluoropolymer dispersion may thereafter be isolated by filtration.
  • the perfluoropolyether surfactant may subsequently be recovered from the anion exchange resin by eluting the loaded resin.
  • a suitable mixture for eluting the anion exchange resin is a mixture of ammonium chloride, methanol and water.
  • the latex particle size determination was conducted by means of dynamic light scattering with a Malvern Zetazizer 1000 HSA in accordance to ISO/DIS 13321. Prior to the measurements, the polymer latexes as yielded from the polymerisations were diluted with 0.001 mol/L KCl-solution, the measurement temperature was 25° C. in all cases. The reported average is the Z-average particle diameter.
  • Polymer Density was measured according to ASTM4894 Method D792.
  • the polymerization experiments were performed in a 40 L autoclave equipped with an impeller agitator and a baffle.
  • the autoclave was evacuated and than charged with 33 l of deionized water and set to 35° C. Agitation was started at 160 rpm and in three following cycles, the vessel was evacuated and subsequently charged with nitrogen to assure that all oxygen had been removed.

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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)
  • Polymerisation Methods In General (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Polyethers (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
  • Paints Or Removers (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
US11/457,500 2005-07-15 2006-07-14 Aqueous emulsion polymerization of fluorinated monomers using a perfluoropolyether surfactant Abandoned US20070015865A1 (en)

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EP (1) EP1904538B1 (fr)
JP (1) JP5021642B2 (fr)
CN (1) CN101218264B (fr)
AT (1) ATE464330T1 (fr)
DE (1) DE602006013641D1 (fr)
GB (1) GB0514387D0 (fr)
RU (1) RU2428434C2 (fr)
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RU2428434C2 (ru) 2011-09-10
GB0514387D0 (en) 2005-08-17
RU2008100105A (ru) 2009-08-20
WO2007011631A1 (fr) 2007-01-25
EP1904538B1 (fr) 2010-04-14
CN101218264B (zh) 2010-09-29
JP5021642B2 (ja) 2012-09-12
ATE464330T1 (de) 2010-04-15
JP2009501808A (ja) 2009-01-22
DE602006013641D1 (de) 2010-05-27
EP1904538A1 (fr) 2008-04-02

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