WO2008079394A1 - Crosslinkable vinyl fluoride copolymers - Google Patents

Crosslinkable vinyl fluoride copolymers Download PDF

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Publication number
WO2008079394A1
WO2008079394A1 PCT/US2007/026286 US2007026286W WO2008079394A1 WO 2008079394 A1 WO2008079394 A1 WO 2008079394A1 US 2007026286 W US2007026286 W US 2007026286W WO 2008079394 A1 WO2008079394 A1 WO 2008079394A1
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WO
WIPO (PCT)
Prior art keywords
vinyl fluoride
monomer
copolymer
mole
fluoride copolymer
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/US2007/026286
Other languages
English (en)
French (fr)
Inventor
Ronald Earl Uschold
Jian Wang
Masahiro Yamamoto
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.)
Chemours Mitsui Fluoroproducts Co Ltd
EIDP Inc
Original Assignee
Du Pont Mitsui Fluorochemicals Co Ltd
EI Du Pont de Nemours and Co
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 Du Pont Mitsui Fluorochemicals Co Ltd, EI Du Pont de Nemours and Co filed Critical Du Pont Mitsui Fluorochemicals Co Ltd
Priority to CA 2671991 priority Critical patent/CA2671991A1/en
Priority to KR1020097015151A priority patent/KR101458652B1/ko
Priority to CN2007800468058A priority patent/CN101563375B/zh
Priority to AU2007338712A priority patent/AU2007338712B2/en
Priority to EP20070868002 priority patent/EP2094747B1/en
Priority to JP2009542965A priority patent/JP5166440B2/ja
Publication of WO2008079394A1 publication Critical patent/WO2008079394A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/18—Manufacture of films or sheets
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F214/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
    • C08F214/18—Monomers containing fluorine
    • C08F214/20—Vinyl fluoride
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F214/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
    • C08F214/18—Monomers containing fluorine
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F214/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
    • C08F214/18—Monomers containing fluorine
    • C08F214/20—Vinyl fluoride
    • C08F214/202—Vinyl fluoride with fluorinated vinyl ethers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F214/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
    • C08F214/18—Monomers containing fluorine
    • C08F214/26—Tetrafluoroethene
    • C08F214/262—Tetrafluoroethene with fluorinated vinyl ethers
    • 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
    • C08L27/14—Homopolymers or copolymers of vinyl fluoride
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D127/00—Coating compositions based on 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; Coating compositions based on derivatives of such polymers
    • C09D127/02—Coating compositions based on 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; Coating compositions based on derivatives of such polymers not modified by chemical after-treatment
    • C09D127/12—Coating compositions based on 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; Coating compositions based on derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms
    • C09D127/14—Homopolymers or copolymers of vinyl fluoride
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10F—INORGANIC SEMICONDUCTOR DEVICES SENSITIVE TO INFRARED RADIATION, LIGHT, ELECTROMAGNETIC RADIATION OF SHORTER WAVELENGTH OR CORPUSCULAR RADIATION
    • H10F19/00—Integrated devices, or assemblies of multiple devices, comprising at least one photovoltaic cell covered by group H10F10/00, e.g. photovoltaic modules
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    • C08J2300/00—Characterised by the use of unspecified polymers
    • C08J2300/22—Thermoplastic resins
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    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
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Definitions

  • the fluorine atoms in PVF are largely responsible for its properties of excellent weatherability, chemical resistance and mechanical properties. Enhancement of these properties may be achieved with polymers of higher fluorine content.
  • One way to increase polymer fluorine content is to prepare copolymers in which tetrafluoroethylene (TFE) replaces some of the vinyl fluoride (VF).
  • TFE tetrafluoroethylene
  • VF vinyl fluoride
  • dipolymers have been described by Coffman and Ford, U.S. Patent No. 2,419,009 (1947); Sianesi and Caporiccio, J. Polymer Sci., Part A-1 , 6, (1968) 335, and U.S. Patent No. 3,513,116 (1970).
  • Another way is reported in Stilmar, U.S. Pat. No.
  • the present invention provides a vinyl fluoride copolymer comprising: about 40 to about 90 mole % of repeat units derived from vinyl fluoride; and about 10 to about 60 mole % of repeat units derived from monomer selected from the group consisting of (a) and (b) below and mixtures thereof, with the proviso that about 0.1 mole % to 50 mole % of repeat units in the copolymer are derived from monomer selected from (b):
  • monomer (b) is fluorinated vinyl monomer containing the at least one functional group, and more preferably, (b) is fluorinated vinyl ether monomer containing the at least one functional group.
  • monomer (a) comprises tetrafluoroethylene.
  • the invention can be embodied as fluoropolymer blend comprising the vinyl fluoride copolymer and at least one fluoropolymer different from the vinyl fluoride copolymer.
  • the invention further provides a shaped article made from dispersions or solutions of the vinyl fluoride copolymer, preferably in the form of films.
  • a shaped article can also be made by molding the vinyl fluoride copolymer.
  • the vinyl fluoride copolymer in accordance with the invention is readily used to make protective coatings and processed into articles such as films from dispersion or solution form. Desirable mechanical properties and/or adhesiveness to substrates can be obtained by crosslinking.
  • monomer (c) Especially preferred for monomer (c) are perfluoroolefins having 3-10 carbon atoms, perfluoro C1-C8 alkyl ethylenes, and fluorinated vinyl ethers. Most preferably, highly fluorinated vinyl ethers and perfluoro C1-C8 alkyl ethylenes are used.
  • the functional groups of monomer (b) provide a cross- linkable reaction site and the introduced functional group (and side chain if present) may also improve the solubility of the copolymer in organic solvents to improve processability of the vinyl fluoride copolymer of the invention.
  • units derived from monomer (b) are present in an amount of about 0.1 mole % to 50 mole %, preferably about 0.1 mole % to about 40 mole %, and more preferably, about 0.2 mole % to 30 mole %, and most preferably, about 0.2 mole % to about 20 mole %.
  • the ability of the various vinyl monomers with functional groups to form cross-links and adjust solubility characteristics will vary with the particular monomer(s) employed so sufficient quantity of such monomers should be employed to provide the desired effect.
  • Polymerization temperatures of about 4O 0 C to 15O 0 C are suitable, preferably 6O 0 C to 100 0 C and pressures of about 1 MPa to 12 MPa (145 psi to 1 ,760 psi) may be used.
  • a buffering agent such as phosphate, carbonate and acetate can be used for controlling pH of the latex.
  • the crosslinkable compositions in accordance with the invention are employed similarly to other cross-linkable compositions as are known in the art and are especially useful as coatings and in the production of films.
  • a coating composition which comprises the cross-linkable polymeric composition and a liquid medium with the copolymer being dispersed or dissolved in the medium.
  • the crosslinking agent employed in the composition is preferably soluble in the coating composition medium and is reactive with the types of functional groups provided in the copolymer my monomer (b).
  • the composition will be applied to a substrate and heated to remove the liquid medium. If the copolymer is in dispersion form, heating may also be needed to coalesce the copolymer.
  • Preferred fluoropolymers includes polyvinyl fluoride (PVF), polyvinylidene fluoride (PVdF), VF-TFE copolymer, VF-TFE-perfluoroalkyl vinyl ether (PAVE) copolymer, VdF-hexafluoropropene (HFP) copolymer, VdF-TFE-HFP copolymer and VdF-TFE-PAVE copolymer and the like.
  • copolymer in accordance with the present invention in resin form can be suitably formed into a shaped article by molding. Molding can be carried out using techniques known in the art which have been adapted for the characteristics of the copolymer being processed.
  • a film is prepared using a 10% solution of the vinyl fluoride copolymers in NMP 1 and tensile properties are measured using TENSILON (UTM-1T, made by TOYO BALDWIN Co. Ltd.)
  • An initiator solution is prepared by dissolving 20 g of ammonium persulfate in 1 L of deionized water. This initiator solution is supplied into the reactor at a rate of 25 ml/minute for 5 minutes, and then the rate is lowered and maintained at 1 ml/minute during the reaction. When the internal pressure drops to 3.0 MPa, the makeup monomer mixtures shown in Table 2 are supplied to keep the pressure constant.
  • composition of this makeup supply is different from that of the pre- charged mixture because of different reactivity of each monomer. Since the composition thereof is selected so that the monomer composition in the reactor is kept constant, a product having a uniform composition is obtained.
  • Monomers are supplied to the autoclave until a solid content in the produced latex reaches about 20%. When the solid content reaches a predetermined value, supply of the monomers is immediately stopped, then the content of the autoclave is cooled and unreacted gases in the autoclave are purged off.
  • VF copolymer is dissolved in NMP at 55 to 6O 0 C using a water-bath incubator and then cooled to room temperature (25 0 C), and solubility of the resin, at which a stable clear solution is obtained, is measured.
  • Table 3 The results are shown in Table 3.
  • Resin solutions are prepared by dissolving the vinyl fluoride-based copolymers synthesized in Examples 1 - 7 at 50 to 7O 0 C in N-methyl-2- pyrrolidone.
  • Titanium acetylacetonate (TYZORO AA 75, made by DuPont Co.) is selected as a cross-linking agent.
  • This cross-linking agent is dissolved in N-methyl-2-pyrrolidone to provide a 10% solution.
  • the above solution of the cross-linking agent, titanium acetylacetonate is added to the resin solution in amounts of 1 %, 3% and 5% (% is by weight relative to the vinyl fluoride-based copolymer resin), and mixed uniformly.
  • the resulting films peel off completely from the aluminum substrates.
  • the resulting films of Examples 13-16 which employ crosslinking agents show excellent adhesiveness to the aluminum substrates.
  • the resulting films of Examples 8-12 with partial crosslinking reactions show fair adhesiveness.
  • Examples 23-25 illustrate tensile strengths and elongations at break measured by TENSILON of VF copolymer films prepared in Examples 12, 17 and 22. The results are shown in Table 5.
  • Table 5 Table 5
  • cross-linked resins of the invention have good mechanical properties such as high maximum stress and elongation at break values.
  • aqueous dispersions of crosslinkable vinyl fluoride-based copolymers having the polymer compositions shown in Table 6 are prepared and examined.
  • the aqueous dispersions and the cross-linking agents (melamine resin, Cymel 350, CYTEC INDUSTRIES INC.) are mixed uniformly.
  • the mixtures are put into aluminum cups (No.107, made by AS ONE Corp.) and subjected to drying and cross-linking at 19O 0 C for 5 hours in a vacuum dryer. After cooling to room temperature, the resulting coatings are evaluated by visual observation. The results are shown in Table 6.

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PCT/US2007/026286 2006-12-21 2007-12-21 Crosslinkable vinyl fluoride copolymers Ceased WO2008079394A1 (en)

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CN2007800468058A CN101563375B (zh) 2006-12-21 2007-12-21 可交联的氟乙烯共聚物
AU2007338712A AU2007338712B2 (en) 2006-12-21 2007-12-21 Crosslinkable vinyl fluoride copolymers
EP20070868002 EP2094747B1 (en) 2006-12-21 2007-12-21 Crosslinkable vinyl fluoride copolymers
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WO2008079395A1 (en) 2008-07-03
EP2094748B1 (en) 2012-10-17
AU2007338712B2 (en) 2013-03-07
EP2094747A1 (en) 2009-09-02
KR20090094039A (ko) 2009-09-02
AU2007338712A1 (en) 2008-07-03
CA2671991A1 (en) 2008-07-03
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AU2007338713A1 (en) 2008-07-03
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EP2094748A1 (en) 2009-09-02
US7842765B2 (en) 2010-11-30
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US20080156367A1 (en) 2008-07-03
EP2094747B1 (en) 2012-10-17
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