WO2017172564A2 - Multilayer fluoropolymer films - Google Patents

Multilayer fluoropolymer films Download PDF

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Publication number
WO2017172564A2
WO2017172564A2 PCT/US2017/024225 US2017024225W WO2017172564A2 WO 2017172564 A2 WO2017172564 A2 WO 2017172564A2 US 2017024225 W US2017024225 W US 2017024225W WO 2017172564 A2 WO2017172564 A2 WO 2017172564A2
Authority
WO
WIPO (PCT)
Prior art keywords
layer
multilayer
polymer
film
fluoropolymer film
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/US2017/024225
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English (en)
French (fr)
Other versions
WO2017172564A3 (en
Inventor
Timothy J. Hebrink
Joseph A. Richie
Jacob D. YOUNG
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.)
3M Innovative Properties Co
Original Assignee
3M Innovative Properties 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 3M Innovative Properties Co filed Critical 3M Innovative Properties Co
Priority to CN201780019664.4A priority Critical patent/CN108883617B/zh
Priority to US16/086,138 priority patent/US11254104B2/en
Priority to JP2018551174A priority patent/JP6949048B2/ja
Priority to KR1020187031284A priority patent/KR102369406B1/ko
Priority to EP17717577.5A priority patent/EP3436263B1/en
Publication of WO2017172564A2 publication Critical patent/WO2017172564A2/en
Publication of WO2017172564A3 publication Critical patent/WO2017172564A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/06—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material
    • B32B27/08—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/18—Layered products comprising a layer of synthetic resin characterised by the use of special additives
    • B—PERFORMING OPERATIONS; TRANSPORTING
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    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/18—Layered products comprising a layer of synthetic resin characterised by the use of special additives
    • B32B27/20—Layered products comprising a layer of synthetic resin characterised by the use of special additives using fillers, pigments, thixotroping agents
    • B—PERFORMING OPERATIONS; TRANSPORTING
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    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/28—Layered products comprising a layer of synthetic resin comprising synthetic resins not wholly covered by any one of the sub-groups B32B27/30 - B32B27/42
    • B32B27/285—Layered products comprising a layer of synthetic resin comprising synthetic resins not wholly covered by any one of the sub-groups B32B27/30 - B32B27/42 comprising polyethers
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    • B32B27/304—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers comprising vinyl halide (co)polymers, e.g. PVC, PVDC, PVF, PVDF
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    • B32B37/153—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding characterised by the properties of the layers with at least one layer being manufactured and immediately laminated before reaching its stable state, e.g. in which a layer is extruded and laminated while in semi-molten state at least one layer is extruded and immediately laminated while in semi-molten state
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    • B32B7/04—Interconnection of layers
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Definitions

  • Advantages of embodiments of multilayer fiuoropolymer films described herein include desirable resistance to staining, to UV damage, and/or to solvent damage. Some embodiments of multilayer fiuoropolymer films described herein are useful, for example in multilayer film applications (e.g., retro-reflective traffic signs, commercial graphics, automotive paint, windows, windshields, building exteriors, and photo voltaics).
  • multilayer film applications e.g., retro-reflective traffic signs, commercial graphics, automotive paint, windows, windshields, building exteriors, and photo voltaics.
  • First layer 101 comprises a first polymer, the first polymer comprises at least 35 mol percent tetrafiuoroethylene comonomer, at least 15 mole percent vinylidene fluoride comonomer, and at least 5 mol percent hexafluoropropylene comonomer, based on the total mol percent of the first polymer.
  • Second layer 102 comprises a second polymer, the second polymer comprises at least 50 mol percent vinylidene fluoride comonomer, based on the total mol percent of the second polymer.
  • the first polymer of multilayer fluoropolymer films described herein further comprises at least 0.5 (in some embodiments, at least 1, 5, 10, 25, or even at least 50; in some embodiments, in a range from 0.5 to 50, or even 1 to 10) mol percent perfluorovinylether comonomer, based on the total mol percent of the first polymer.
  • Exemplary polymers for the third layer of the multilayer fluoropolymer films described herein include polymethylmethacrylate (PMMA) (available, for example, from Arkema, Bristol, PA, under the trade designation "V044"), PMMA-butylacrylate block copolymer (available, for example, from Kuraray Ltd., Osaka, Japan, under the trade designation "LA4285”), and polymer blends thereof.
  • PMMA polymethylmethacrylate
  • V044 PMMA-butylacrylate block copolymer
  • LA4285 polymer blends thereof.
  • Exemplary olefin copolymers for the optional fourth layer are available, for example, from E.I. DuPont de Nemours & Co., Wilmington, DE, under the trade designations "EL VAX” and "BYNEL.”
  • An exemplary polycarbonate polymer for the optional fourth layer is available, for example, from SABIC Innovative Plastics, Pittsfield, MA, under the trade designation "LEXAN.”
  • Exemplary extrudable adhesives for the optional fourth layer include isobutylene/isoprene copolymers available, for example, from Exxon Mobil Corp., under the trade designations "EXXON BUTYL 065,” “EXXON BUTYL 068,” and “EXXON BUTYL 268" (believed to have an unsaturation in the range of about 1.05 to about 2.30 mole percent); United Chemical Products, Velizy-Villacoublay, France, under the trade designation “BK-1675N” (believed to have unsaturation of about 1.7 mole percent); LANXESS, Sarnia, Ontario, Canada, under the trade designation “LANXESS BUTYL 301” (believed to have unsaturation of about 1.85 mole percent), “LANXESS BUTYL 101-3” (believed to have unsaturation of about 1.75 mole percent), and “LANXESS BUTYL 402" (believed to have unsaturation of about 2.25 mole percent); and Kaneka,
  • suitable polyisobutylenes may have a wide variety of molecular weights and a wide variety of viscosities.
  • the polyisobutylene has a weight average molecular weight (as measured by Gel Permeation Chromatography using polystyrene standards) of at least about 300,000 (in some embodiments, at least about 400,000, or even at least 500,000 or more) grams per mole.
  • the polyisobutylene has a weight average molecular weight of less than 300,000 (in some embodiments, up to 280,000, 275,000, 270,000, 260,000, 250,000, 240,000, 230,000, 220,000, 210,000, or up to 200,000) grams per mole.
  • PSA layers can be provided by techniques known in the art, such as hot melt extrusion of an extrudable composition comprising the components of the PSA composition.
  • the PSA layer can be made by this process in the absence of solvents. Exemplary methods for making extrudable adhesives are described, for example, in PCT Pub. No. WO 1995/016754A1 (Leonard et. al.), the disclosure of which is incorporated herein by reference.
  • a composite multilayer optical film comprises a first and an optional second multilayer fluoropolymer film described herein, wherein, in order are, the first multilayer fluoropolymer film; a multilayer optical film that has first and second opposed major surfaces; and the optional second multilayer fluoropolymer film, wherein the third layer of the first multilayer fluoropolymer film is adjacent to the first major surface of the multilayer optical film, and wherein the third layer of the second multilayer fluoropolymer film is adjacent to the second major surface of the multilayer optical film.
  • the first multilayer fluoropolymer film a multilayer optical film that has first and second opposed major surfaces
  • the optional second multilayer fluoropolymer film wherein the third layer of the first multilayer fluoropolymer film is adjacent to the first major surface of the multilayer optical film, and wherein the third layer of the second multilayer fluoropolymer film is adjacent to the second major surface of the multilayer optical film.
  • the multilayer optical film comprises at least 2 first optical layers and at least 2 second optical layers (in some embodiments, at least 5 first optical layers and at least 5 second optical layers, at least 50 first optical layers and at least 50 second optical layers, or even at least 200 first optical layers and at least 200 second optical layers).
  • the structured polymer surface is generally formed by extrusion replication where a thermoplastic resin such as a fluoropolymer is extruded using standard extrusion equipment and fed through a die and into a nip with a machined metal tool roll and a rubber roll. The molten polymer is quenched while in contact with the tool surface, which then releases from the tool roll and is wound on a roll.
  • a thermoplastic resin such as a fluoropolymer
  • Light energy absorbing devices, and especially the structured face of the anti-reflective structured film may be exposed to a variety of detrimental conditions from outside environments.
  • the structured face can be exposed to environmental elements such as rain, wind, hail, snow, ice, and blowing sand, which can damage the structured surface of the structured face.
  • environmental elements such as rain, wind, hail, snow, ice, and blowing sand, which can damage the structured surface of the structured face.
  • long term exposure to other environmental conditions such as heat and UV radiation exposure from the sun can also cause degradation of the structured face.
  • many polymeric organic materials are susceptible to breaking down upon repeated exposure to UV radiation.
  • Weatherability for light energy absorbing devices such as, for example, a solar energy conversion device is generally measured in years, because it is desirable that the materials be able to function for years without deterioration or loss of performance.
  • a multilayer fluoropolymer film comprising, in order:
  • the multilayer fluoropolymer film of any preceding Exemplary Embodiment having an interlayer adhesion between the second and third layers as determined by the Interlayer Adhesion Test of at least 40 (in some embodiments, at least 50, 75, 100, 150, 200, 250, 300, 350, 400, 450, or even at least 500; in some embodiments, in a range from 40 to 500 or even 50 to 500) g/cm.
  • a multilayer film comprising a series of at least 100 repeating multilayer fluoropolymer films of any of Exemplary Embodiments 1 to 24.
  • the surface gloss of the laminated film to be tested was measured using the gloss meter ("MICRO-TRI-GLOSS").
  • the surface of the film to be tested was rubbed with a cloth (“WYPALL L40") that had been saturated with 10 ml of isopropyl alcohol (IPA) using a wear tester (obtained from Paul N. Gardner Company, Pompano Beach, FL, under the trade designation "WASHABILITY AND WEAR TESTER MODEL D10V”) under the following conditions: a 404 gram sled with 3.5 cm by 8.5 cm foot print, 40 passes of the sled at 33 cm/sec.
  • the gloss of rubbed film surface tested using the gloss meter (“MICRO-TRI-GLOSS").
  • 3M Dyneon under the trade designation "FLUOROPLASTIC GRANULES THV815GZ" and a fluoropolymer second layer (“3M DYNEON FLUOROPLASTIC GRANULES PVDF 1 1010/0000”) using a 3 layer multi-manifold die.
  • the third layer was created using a 50:50 blend of PMMA butylacrylate copolymer ("LA4285”) with PMMA UVA master batch (“TAl 1- 10 MB03”) and fed to the bottom manifold of the multi-manifold die with a 25 mm twin screw extruder at 1.8 kg/hr. (4 lbs./hr.).
  • a multilayer polymeric film was made by coextruding a fluoropolymer first layer ("FLUOROPLASTIC GRANULES THV815GZ”) and a fluoropolymer second layer (obtained from 3M Dyneon, under the trade designation "3M DYNEON FLUOROPLASTIC GRANULES PVDF 6008/0001" using a 3 layer multi-manifold die.
  • FLUOROPLASTIC GRANULES THV815GZ fluoropolymer first layer
  • a fluoropolymer second layer obtained from 3M Dyneon, under the trade designation "3M DYNEON FLUOROPLASTIC GRANULES PVDF 6008/0001"

Landscapes

  • Laminated Bodies (AREA)
  • Extrusion Moulding Of Plastics Or The Like (AREA)
PCT/US2017/024225 2016-04-01 2017-03-27 Multilayer fluoropolymer films Ceased WO2017172564A2 (en)

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CN201780019664.4A CN108883617B (zh) 2016-04-01 2017-03-27 多层含氟聚合物膜
US16/086,138 US11254104B2 (en) 2016-04-01 2017-03-27 Multilayer fluoropolymer films
JP2018551174A JP6949048B2 (ja) 2016-04-01 2017-03-27 多層フルオロポリマーフィルム
KR1020187031284A KR102369406B1 (ko) 2016-04-01 2017-03-27 다층 플루오로중합체 필름
EP17717577.5A EP3436263B1 (en) 2016-04-01 2017-03-27 Multilayer fluoropolymer films

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US201662316965P 2016-04-01 2016-04-01
US62/316,965 2016-04-01

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EP (1) EP3436263B1 (enExample)
JP (1) JP6949048B2 (enExample)
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US11654664B2 (en) 2020-01-16 2023-05-23 3M Innovative Properties Company Composite cooling film comprising a reflective nonporous organic polymeric layer and a UV-protective layer
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JP2019511400A (ja) 2019-04-25
US11254104B2 (en) 2022-02-22
EP3436263A2 (en) 2019-02-06
CN108883617A (zh) 2018-11-23
JP6949048B2 (ja) 2021-10-13
WO2017172564A3 (en) 2017-12-28
US20190111666A1 (en) 2019-04-18
KR102369406B1 (ko) 2022-03-02
CN108883617B (zh) 2020-09-15
EP3436263B1 (en) 2023-09-13

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