WO2002016517A2 - Fluoroalkyl (meth)acrylate copolymer coating compositions - Google Patents

Fluoroalkyl (meth)acrylate copolymer coating compositions Download PDF

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Publication number
WO2002016517A2
WO2002016517A2 PCT/US2001/025527 US0125527W WO0216517A2 WO 2002016517 A2 WO2002016517 A2 WO 2002016517A2 US 0125527 W US0125527 W US 0125527W WO 0216517 A2 WO0216517 A2 WO 0216517A2
Authority
WO
WIPO (PCT)
Prior art keywords
group
meth
coating composition
fluorocopolymer
carbon atoms
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/US2001/025527
Other languages
English (en)
French (fr)
Other versions
WO2002016517A3 (en
Inventor
Patricia M. Savu
Richard M. Flynn
Michael J. Parent
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 AU2001283381A priority Critical patent/AU2001283381A1/en
Priority to DE60118576T priority patent/DE60118576T2/de
Priority to KR1020037002284A priority patent/KR100807896B1/ko
Priority to JP2002521601A priority patent/JP5220978B2/ja
Priority to EP01962184A priority patent/EP1311637B8/en
Publication of WO2002016517A2 publication Critical patent/WO2002016517A2/en
Publication of WO2002016517A3 publication Critical patent/WO2002016517A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • C09D133/00—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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
    • C09D133/04—Homopolymers or copolymers of esters
    • C09D133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
    • C09D133/16—Homopolymers or copolymers of esters containing halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/62—Halogen-containing esters
    • C07C69/63—Halogen-containing esters of saturated acids
    • 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
    • C08F120/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F120/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F120/10—Esters
    • C08F120/22—Esters containing halogen
    • C08F120/24—Esters containing halogen containing perhaloalkyl radicals
    • 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
    • C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/10—Esters
    • C08F20/22—Esters containing halogen
    • C08F20/24—Esters containing halogen containing perhaloalkyl radicals

Definitions

  • fluorinated coatings containing fluoroalkyl groups e.g., coatings made by polymerizing fluoroalkyl (meth)acrylates
  • the surface energy of the fluoropolymer coatings would be related to the chain length of the fluoroalkyl group of the fluoropolymer coating.
  • (meth)acrylic acid refers to both acrylates and methacrylates
  • (meth)acrylic acid refers to both acrylic acid and methacrylic acid.
  • the (meth)acrylate is derived from an alcohol selected from CF 3 CHFCF 2 CH 2 OH, HCF 2 CF 2 CH 2 OH, C 2 F 5 CH(OH)CF(CF 3 )2, C 3 F 7 CH 2 OH, and
  • hydrofluorocarbon means compounds consisting only of the elements carbon, hydrogen and fluorine.
  • the carbon backbone of the HFC can be straight, branched, cyclic, or mixtures of these, and can contain from 3 to 8 carbon atoms.
  • Useful HFCs include compounds having more than approximately 5 molar percent fluorine substitution, or less than 95 molar percent fluorine substitution, based on the total number of hydrogen and fluorine atoms bonded to carbon, such compounds including CF3CFHCFHCF2CF3, C-sFn H, CsF ⁇ H,
  • R-0 x -R' f (ll) wherein x is 1 or 2; R represents an alkyl group having about 1 to 4 carbon atoms; and R' f represents a fluoroaliphatic group.
  • the barrier coating is of a size and shape, adjacent to the area of lubrication, sufficient to prevent migration of the lubricant, and may surrounds the lubricant and therefor containing it in the desired area of lubrication.
  • the fluorocopolymer could be coated in the shape of a ring surrounding a quantity of lubricant in contact with the lubricated surfaces.
  • Any suitable lubricants may be used, in udjng ⁇ sijicones, petroleum oils and greases, aliphatic diester oils and polyether oils.
  • the antimigration coatings may be used to contain other fluids subject to migrations, such as inks and fluxes.
  • sliders are employed to aerodynamically fly a magnetic transducer over the surface of the disk.
  • the slider forms a pressure region to develop the desired pressure between the slider and disk surface to achieve the desired flying characteristics for the slider.
  • One problem associated with air-bearing sliders is that the liquid lubricant on the surface of the disk can transfer to the slider by wicking when the media has stopped spinning and the slider rests on the disk. This wicking, along with the accumulation of other debris such as dust, increase stiction between the slider and the disk, thus requiring additional power to take off the slider. Additionally any lubricant that wicks to the surface of the slider, and any debris which collects thereon, can adversely affect the flying characteristics of the slider.
  • the pellicle film comprises a film of the present fluorocopolymer less than 5 micrometers, and preferably less than 1.2 micrometers.
  • the pellicle film may comprise a coating of the fluorocopolymer on a conventionally pellicle film such as nitrocellulose or other cellulosic polymer.
  • a freestanding film of the fluorocopolymer may be prepared by any conventional technique such a blown films, or by casting either neat or from a suitable solvent.
  • the low surface energy of the fluorocopolymer makes it easier to remove contaminants, such as dust, from the pellicle, by brushing or blowing. Additionally, the fluorocopolymers are not subject to the build-up of static charges that attract and hold particulate contaminants on the pellicle surface.
  • the 99/1 copolymer of 1 ,1 -dihydroperfluorocyclohexylmethyl methacrylate/acrylic acid was prepared using essentially the same procedure as described for Fluorocopolymer 1 except that an equal weight of 1 ,1 - dihydroperfluorocyclohexylmethyl methacrylate was substituted for the 2,2,3,3,4,4,4-heptafluorobutyl methacrylate.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Paints Or Removers (AREA)
  • Materials Applied To Surfaces To Minimize Adherence Of Mist Or Water (AREA)
  • Adjustment Of The Magnetic Head Position Track Following On Tapes (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Application Of Or Painting With Fluid Materials (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Synthetic Leather, Interior Materials Or Flexible Sheet Materials (AREA)
PCT/US2001/025527 2000-08-18 2001-08-15 Fluoroalkyl (meth)acrylate copolymer coating compositions Ceased WO2002016517A2 (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
AU2001283381A AU2001283381A1 (en) 2000-08-18 2001-08-15 Fluoroalkyl (meth)acrylate copolymer coating compositions
DE60118576T DE60118576T2 (de) 2000-08-18 2001-08-15 Fluoro(meth)acrylatecopolymer-beschichtungsmassen
KR1020037002284A KR100807896B1 (ko) 2000-08-18 2001-08-15 플루오로알킬 (메트)아크릴레이트 공중합체 코팅 조성물
JP2002521601A JP5220978B2 (ja) 2000-08-18 2001-08-15 フルオロアルキル（メタ）アクリレートコポリマーコーティング組成物
EP01962184A EP1311637B8 (en) 2000-08-18 2001-08-15 Fluoroalkyl (meth)acrylate copolymer coating compositions

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US22623500P 2000-08-18 2000-08-18
US60/226,235 2000-08-18

Publications (2)

Publication Number Publication Date
WO2002016517A2 true WO2002016517A2 (en) 2002-02-28
WO2002016517A3 WO2002016517A3 (en) 2002-05-23

Family

ID=22848098

Family Applications (2)

Application Number Title Priority Date Filing Date
PCT/US2001/025527 Ceased WO2002016517A2 (en) 2000-08-18 2001-08-15 Fluoroalkyl (meth)acrylate copolymer coating compositions
PCT/US2001/025626 Ceased WO2002016306A2 (en) 2000-08-18 2001-08-16 Degradable, amorphous, fluoroacrylate polymers

Family Applications After (1)

Application Number Title Priority Date Filing Date
PCT/US2001/025626 Ceased WO2002016306A2 (en) 2000-08-18 2001-08-16 Degradable, amorphous, fluoroacrylate polymers

Country Status (8)

Country Link
US (1) US6649719B2 (enExample)
EP (2) EP1311637B8 (enExample)
JP (3) JP5220978B2 (enExample)
KR (2) KR100807896B1 (enExample)
AT (1) ATE322524T1 (enExample)
AU (2) AU2001283381A1 (enExample)
DE (2) DE60118576T2 (enExample)
WO (2) WO2002016517A2 (enExample)

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WO2003089712A1 (en) * 2002-04-17 2003-10-30 3M Innovative Properties Company Repellent fluorochemical compositions
US6894105B2 (en) 2002-07-26 2005-05-17 3M Innovatives Properties Company Dyed fluoropolymers
US6930184B2 (en) 2002-07-26 2005-08-16 3M Innovative Properties Company Functional fluorescent dyes
WO2007061329A1 (fr) * 2005-11-25 2007-05-31 Pfc-Tec Llc Procede pour produire un composant filmogene fluore a faible poids moleculaire et composition sur cette base
US7531730B2 (en) * 2005-02-08 2009-05-12 Phillip Jason Everly Non-toxic chemical musical instrument string coating and preservative
US7576099B2 (en) * 2005-02-28 2009-08-18 Renovis, Inc. Amide derivatives as ion-channel ligands and pharmaceutical compositions and methods of using the same
US7923133B2 (en) 2007-12-21 2011-04-12 3M Innovative Properties Company Coatings and methods for particle reduction
US7951524B2 (en) 2006-04-28 2011-05-31 International Business Machines Corporation Self-topcoating photoresist for photolithography
US8034532B2 (en) * 2006-04-28 2011-10-11 International Business Machines Corporation High contact angle topcoat material and use thereof in lithography process
US8319095B2 (en) * 2007-11-27 2012-11-27 Guardian Industries Corp. Method of making an antireflective silica coating, resulting product, and photovoltaic device comprising same
US8945808B2 (en) 2006-04-28 2015-02-03 International Business Machines Corporation Self-topcoating resist for photolithography
US9029452B2 (en) 2010-05-27 2015-05-12 E I Du Pont De Nemours And Company Fluoropolymer additive for coatings
US9290596B2 (en) 2010-05-27 2016-03-22 The Chemours Company Fc, Llc Solvent-based fluoropolymer additives and their use in coating compositions
WO2017189388A1 (en) 2016-04-25 2017-11-02 3M Innovative Properties Company Composite particles for curing epoxy resin compositions and curable and cured epoxy resin compositions prepared using the particles
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JP5220978B2 (ja) 2013-06-26
WO2002016306A3 (en) 2003-03-20
DE60131671T2 (de) 2008-10-30
KR100807896B1 (ko) 2008-02-27
DE60118576T2 (de) 2006-11-02
EP1311637A2 (en) 2003-05-21
US6649719B2 (en) 2003-11-18
KR20030031981A (ko) 2003-04-23
DE60131671D1 (en) 2008-01-10
EP1326902B1 (en) 2007-11-28
KR20030027034A (ko) 2003-04-03
JP2013028807A (ja) 2013-02-07
DE60118576D1 (de) 2006-05-18
WO2002016306A2 (en) 2002-02-28
EP1311637B1 (en) 2006-04-05
KR100808711B1 (ko) 2008-02-29
WO2002016517A3 (en) 2002-05-23
AU2001283381A1 (en) 2002-03-04
ATE322524T1 (de) 2006-04-15
JP2004506810A (ja) 2004-03-04
EP1326902A2 (en) 2003-07-16

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