EP2275598A1 - Oberflächenbehandlung - Google Patents

Oberflächenbehandlung Download PDF

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Publication number
EP2275598A1
EP2275598A1 EP10009211A EP10009211A EP2275598A1 EP 2275598 A1 EP2275598 A1 EP 2275598A1 EP 10009211 A EP10009211 A EP 10009211A EP 10009211 A EP10009211 A EP 10009211A EP 2275598 A1 EP2275598 A1 EP 2275598A1
Authority
EP
European Patent Office
Prior art keywords
plasma
fabric
substrate
formula
oil
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.)
Granted
Application number
EP10009211A
Other languages
English (en)
French (fr)
Other versions
EP2275598B1 (de
Inventor
Jas Pal Singh Badyal
Stephen Richard Coulson
Colin Robert Willis
Stuart Anson Brewer
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.)
P2i Ltd
Original Assignee
UK Secretary of State for Defence
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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=10814111&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=EP2275598(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by UK Secretary of State for Defence filed Critical UK Secretary of State for Defence
Priority claimed from EP19980928453 external-priority patent/EP0988412B1/de
Publication of EP2275598A1 publication Critical patent/EP2275598A1/de
Application granted granted Critical
Publication of EP2275598B1 publication Critical patent/EP2275598B1/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M10/00—Physical treatment of fibres, threads, yarns, fabrics or fibrous goods made from such materials, e.g. by ultrasonic waves, corona discharge, irradiation, electric currents or magnetic fields; Physical treatment combined with treatment with chemical compounds or elements
    • D06M10/02—Sonic or ultrasonic waves; Corona discharge
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M10/00—Physical treatment of fibres, threads, yarns, fabrics or fibrous goods made from such materials, e.g. by ultrasonic waves, corona discharge, irradiation, electric currents or magnetic fields; Physical treatment combined with treatment with chemical compounds or elements
    • D06M10/02—Sonic or ultrasonic waves; Corona discharge
    • D06M10/025—Corona discharge or low temperature plasma
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M14/00—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials
    • D06M14/18—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials using wave energy or particle radiation
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M14/00—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials
    • D06M14/18—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials using wave energy or particle radiation
    • D06M14/20—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials using wave energy or particle radiation on to materials of natural origin
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/263—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof
    • D06M15/277—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof containing fluorine
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
    • D06M2200/10—Repellency against liquids
    • D06M2200/11—Oleophobic properties
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
    • D06M2200/10—Repellency against liquids
    • D06M2200/12—Hydrophobic properties

Definitions

  • a particular substrate which requires such coatings are fabrics, in particular for outdoor clothing applications, sportswear, leisurewear and in military applications. Their treatments generally require the incorporation of a fluoropolymer into or more particularly, fixed onto the surface of the clothing fabric.
  • the degree of oil and water repellency is a function of the number and length of fluorocarbon groups or moieties that can be fitted into the available space. The greater the concentration of such moieties, the greater the repellency of the finish.
  • Japanese application no. 816773 describes the plasma polymerisation of compounds including fluorosubstituted acrylates. In that process, a mixture of the fluorosubstituted acrylate compounds and an inert gas are subjected to a glow discharge.
  • Unsaturated organic compounds are those which contain at least one double bond which is capable of reaching to form a polymeric compound.
  • the compounds used in the method of the invention suitably include at least one optionally substituted hydrocarbon chain. Suitable chains, which may be straight or branched, have from 3 to 20 carbon atoms, more suitably from 6 to 12 carbon atoms
  • the alkyl chains suitably comprise 2 or more carbon atoms, suitably from 2-20 carbon atoms and preferably from 6 to 12 carbon atoms.
  • Suitable alkyl groups for R 1 , R 2 and R 3 have from 1 to 6 carbon atoms.
  • a glow discharge is then ignited by applying a high frequency voltage, for example at 13.56MHz.
  • An L-C matching unit (11) and a power meter (12) was used to couple the output of a 13.56 Mhz R.F. generator (13), which was connected to a power supply (14), to copper coils (15) surrounding the reactor vessel (2).
  • This arrangement ensured that the standing wave ratio (SWR) of the transmitted power to partially ionised gas in the reactor vessel (2) could be minimised.
  • a pulsed signal generator (16) was used to trigger the R.F power supply, and a cathode ray oscilloscope (17) was used to monitor the pulse width and amplitude.
  • the reactor vessel (2) was cleaned by soaking overnight: in a chloro bleach bath, then scrubbing with detergent: and finally rinsing with isopropyl alcohol followed by oven drying.
  • the reactor vessel (2) was then incorporated into the assembly as shown in Figure 1 and further cleaned with a 50W air plasma for 30 minutes.
  • the reactor (2) vessel was vented to air and the substrate to be coated (19), in this case a glass slide, was placed in the centre of the chamber defined by the reactor vessel (2) on a glass plate (18). The chamber was then evacuated back down to base pressure (7.2 x 10 -3 mbar).
  • the deposited plasma polymer coatings were characterised immediately after deposition by X-ray photoelectron spectroscopy (XPS). Complete plasma polymer coverage was confirmed by the absence of any Si (2p) XPS signals showing through from the underlying glass substrate.
  • XPS X-ray photoelectron spectroscopy
  • C F 3 and C F 3 groups are the prominent environments in the C(1s) XPS envelope: C F 2 (291.2eV) 61% C F 3 (293.3eV) 12%
  • the water repellency tests comprises placing 3 drops of a standard test liquid consisting of specified proportions of water and isopropyl alcohol by volume onto the plasma polymerised surface. The surface is considered to repel this liquid if after 10 seconds, 2 of the 3 drops do not wet the fabric. Prom this, the water repellency rating is taken as being the test liquid with the greater proportion of isopropyl alcohol which passes the test.
  • the oil repellency test 3 drops of hydrocarbon liquid are placed on the coated surface. If after 30 seconds no penetration or wetting of the fabric at the liquid-fabric interface occurs around 2 of the 3 drops is evident, then the test is passed.
  • the process of the invention can not only enhance the water repellency of such as fabric, and also confer oil repellency, the durability of the coating is higher than that obtained using the known two step grafting polymerisation process.

Landscapes

  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Toxicology (AREA)
  • Physics & Mathematics (AREA)
  • Plasma & Fusion (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Paints Or Removers (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Application Of Or Painting With Fluid Materials (AREA)
  • Materials For Medical Uses (AREA)
  • Treatments Of Macromolecular Shaped Articles (AREA)
  • Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
  • Organic Insulating Materials (AREA)
  • Wrappers (AREA)
  • Polishing Bodies And Polishing Tools (AREA)
EP10009211.3A 1997-06-14 1998-06-11 Oberflächenbehandlung Expired - Lifetime EP2275598B1 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GBGB9712338.4A GB9712338D0 (en) 1997-06-14 1997-06-14 Surface coatings
EP05007277A EP1557489B1 (de) 1997-06-14 1998-06-11 Oberflächenbehandlung
EP19980928453 EP0988412B1 (de) 1997-06-14 1998-06-11 Oberflächenbehandlung

Related Parent Applications (4)

Application Number Title Priority Date Filing Date
EP98928453.4 Division 1998-06-11
EP05007277A Division EP1557489B1 (de) 1997-06-14 1998-06-11 Oberflächenbehandlung
EP19980928453 Division EP0988412B1 (de) 1997-06-14 1998-06-11 Oberflächenbehandlung
EP05007277.6 Division 2005-04-04

Publications (2)

Publication Number Publication Date
EP2275598A1 true EP2275598A1 (de) 2011-01-19
EP2275598B1 EP2275598B1 (de) 2014-12-17

Family

ID=10814111

Family Applications (2)

Application Number Title Priority Date Filing Date
EP10009211.3A Expired - Lifetime EP2275598B1 (de) 1997-06-14 1998-06-11 Oberflächenbehandlung
EP05007277A Expired - Lifetime EP1557489B1 (de) 1997-06-14 1998-06-11 Oberflächenbehandlung

Family Applications After (1)

Application Number Title Priority Date Filing Date
EP05007277A Expired - Lifetime EP1557489B1 (de) 1997-06-14 1998-06-11 Oberflächenbehandlung

Country Status (8)

Country Link
US (1) USRE43651E1 (de)
EP (2) EP2275598B1 (de)
AT (1) ATE500377T1 (de)
DE (1) DE69842159D1 (de)
DK (2) DK2275598T3 (de)
ES (2) ES2357957T3 (de)
GB (2) GB9712338D0 (de)
PT (2) PT1557489E (de)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8852693B2 (en) 2011-05-19 2014-10-07 Liquipel Ip Llc Coated electronic devices and associated methods

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB0206932D0 (en) * 2002-03-23 2002-05-08 Univ Durham Preparation of superabsorbent materials by plasma modification
GB2434368B (en) * 2006-01-20 2010-08-25 P2I Ltd Plasma coated laboratory consumables
GB2434369B (en) * 2006-01-20 2010-08-25 P2I Ltd Plasma coated electrical or electronic devices
DE102006060932A1 (de) * 2006-12-20 2008-07-03 Carl Freudenberg Kg Temperaturstabile plasmabehandelte Gebilde und Verfahren zu deren Herstellung
CN101743353B (zh) * 2007-07-17 2012-11-07 P2I有限公司 通过等离子体接枝聚合使物品具有耐液性的方法
GB0721202D0 (en) * 2007-10-30 2007-12-05 P2I Ltd Novel method
GB2454242A (en) * 2007-11-02 2009-05-06 P2I Ltd Plasma coating
FR2923494B1 (fr) * 2007-11-09 2010-01-15 Hutchinson Membranes imper-respirantes et leur procede de fabrication
GB2475685A (en) * 2009-11-25 2011-06-01 P2I Ltd Plasma polymerization for coating wool
US8551895B2 (en) 2010-12-22 2013-10-08 Kimberly-Clark Worldwide, Inc. Nonwoven webs having improved barrier properties
EP2589438B1 (de) 2011-11-07 2017-05-03 Vlaamse Instelling voor Technologisch Onderzoek (VITO) Plasmaoberflächenaktivierungsverfahren und daraus entstehendes objekt
US9795989B2 (en) 2013-03-15 2017-10-24 Hzo, Inc. Combining different types of moisture-resistant materials
US9668355B2 (en) 2013-03-15 2017-05-30 Hzo Inc. Combining different types of moisture-resistant materials
EP3722500A1 (de) 2013-12-13 2020-10-14 The North Face Apparel Corp. Plasmabehandlungen zur färbung von textilien
GB201403558D0 (en) 2014-02-28 2014-04-16 P2I Ltd Coating
KR20180018675A (ko) 2015-06-09 2018-02-21 피2아이 리미티드 코팅
WO2021236703A1 (en) * 2020-05-19 2021-11-25 Berry Global, Inc. Fabric with improved barrier properties

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1102903A (en) * 1964-02-24 1968-02-14 Daikin Ind Ltd Fluoro alkyl-containing compounds and water- and oil-repellent compositions containing them
EP0049884A1 (de) 1980-10-11 1982-04-21 Daikin Kogyo Co., Ltd. Verfahren zur Erzeugung eines Fluoralkylacrylatpolymerfilmes auf einem Substrat und Verfahren zur Herstellung eines Resistbildes aus diesem Film
JPS57119906A (en) * 1981-01-19 1982-07-26 Daikin Ind Ltd Formation of smooth film on substrate
JPS59222340A (ja) * 1983-05-31 1984-12-14 大日本印刷株式会社 積層体
SU1158634A1 (ru) 1983-02-02 1985-05-30 Ивановский научно-исследовательский экспериментально-конструкторский машиностроительный институт Способ водо- и маслоотталкивающей отделки текстильных материалов
US5041304A (en) 1989-12-13 1991-08-20 Bridgestone Corporation Surface treatment method
JPH0816773A (ja) 1994-06-29 1996-01-19 Matsushita Electric Ind Co Ltd 画像処理方法

Family Cites Families (40)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3102103A (en) 1957-08-09 1963-08-27 Minnesota Mining & Mfg Perfluoroalkyl acrylate polymers and process of producing a latex thereof
GB1106071A (en) * 1964-04-11 1968-03-13 Wilkinson Sword Ltd Improvements in or relating to the treatment of cutting edges
GB1209512A (en) 1968-08-26 1970-10-21 Commissariat Energie Atomique Method and apparatus for analysing an amplitude spectrum
JPS5250739A (en) * 1975-10-20 1977-04-23 Nasa Antireflection coating for plastic lens
DE2900200A1 (de) 1979-01-04 1980-07-17 Bosch Gmbh Robert Messonde mit schutzschicht und verfahren zur herstellung einer schutzschicht auf einer messonde
GB2105729B (en) 1981-09-15 1985-06-12 Itt Ind Ltd Surface processing of a substrate material
JPS59128281A (ja) 1982-12-29 1984-07-24 信越化学工業株式会社 炭化けい素被覆物の製造方法
JPS60119784A (ja) 1983-12-01 1985-06-27 Kanegafuchi Chem Ind Co Ltd 絶縁金属基板の製法およびそれに用いる装置
DE3326376A1 (de) * 1983-07-22 1985-01-31 Siemens AG, 1000 Berlin und 8000 München Verfahren zum erzeugen von glimmpolymerisat-schichten
US4824753A (en) * 1986-04-30 1989-04-25 Minolta Camera Kabushiki Kaisha Carrier coated with plasma-polymerized film and apparatus for preparing same
DE3750115T2 (de) 1986-10-20 1995-01-19 Hitachi Ltd Plasmabearbeitungsgerät.
EP0393271A1 (de) * 1987-08-08 1990-10-24 The Standard Oil Company Dünnschichtüberzüge aus Fluorpolymer und Verfahren zu ihrer Herstellung durch Plasmapolymerisation
US4827870A (en) 1987-10-05 1989-05-09 Honeywell Inc. Apparatus for applying multilayer optical interference coating on complex curved substrates
JP2575186B2 (ja) 1988-06-24 1997-01-22 コニカ株式会社 熱転写印字装置
JPH0657911B2 (ja) * 1988-08-24 1994-08-03 和歌山県 繊維の難燃加工法
US5246782A (en) * 1990-12-10 1993-09-21 The Dow Chemical Company Laminates of polymers having perfluorocyclobutane rings and polymers containing perfluorocyclobutane rings
US5035917A (en) 1989-06-22 1991-07-30 Siemens Aktiengesellschaft Method of preparing layers of vinylidene fluoride polymers and vinylidene fluoride/trifluoroethylene copolymers on a substrate
JP2897055B2 (ja) 1990-03-14 1999-05-31 株式会社ブリヂストン ゴム系複合材料の製造方法
US5244730A (en) * 1991-04-30 1993-09-14 International Business Machines Corporation Plasma deposition of fluorocarbon
US5773098A (en) * 1991-06-20 1998-06-30 British Technology Group, Ltd. Applying a fluoropolymer film to a body
EP0533044B1 (de) * 1991-09-20 1999-12-29 Balzers Aktiengesellschaft Verfahren zur Schutzbeschichtung von Substraten sowie Beschichtungsanlage
US5328576A (en) 1992-04-06 1994-07-12 Plasma Plus Gas plasma treatment for water and oil proofing of fabrics and paper
IL110454A (en) 1993-08-07 1997-07-13 Akzo Nobel Nv Process for plasma treatment of antiballistically effective materials
DE4445427C2 (de) * 1994-12-20 1997-04-30 Schott Glaswerke Plasma-CVD-Verfahren zur Herstellung einer Gradientenschicht
US5662773A (en) * 1995-01-19 1997-09-02 Eastman Chemical Company Process for preparation of cellulose acetate filters for use in paper making
GB9519824D0 (en) 1995-09-29 1995-11-29 Secr Defence Fibre reactive polymers
US6663713B1 (en) 1996-01-08 2003-12-16 Applied Materials Inc. Method and apparatus for forming a thin polymer layer on an integrated circuit structure
US5876753A (en) * 1996-04-16 1999-03-02 Board Of Regents, The University Of Texas System Molecular tailoring of surfaces
US6329024B1 (en) * 1996-04-16 2001-12-11 Board Of Regents, The University Of Texas System Method for depositing a coating comprising pulsed plasma polymerization of a macrocycle
US5888591A (en) * 1996-05-06 1999-03-30 Massachusetts Institute Of Technology Chemical vapor deposition of fluorocarbon polymer thin films
US6475353B1 (en) 1997-05-22 2002-11-05 Sony Corporation Apparatus and method for sputter depositing dielectric films on a substrate
WO1998058117A1 (en) 1997-06-14 1998-12-23 The Secretary Of State For Defence Surface coatings
US6594158B2 (en) 1997-06-23 2003-07-15 University Of Central Florida AC/DC converter with power factor correction (PFC)
AU744202B2 (en) 1997-08-08 2002-02-21 Board Of Regents Non-fouling, wettable coated devices
PT1179035E (pt) 1999-03-18 2004-10-29 Akzo Nobel Coatings Int Bv Composicao de revestimento para substractos metalicos
EA006831B1 (ru) 2000-10-04 2006-04-28 Дау Корнинг Айэлэнд Лимитед Способ и устройство для образования покрытия
EP1390421A1 (de) 2001-05-23 2004-02-25 NKT Research & Innovation A/S Plasmapolymerisationsverfahren von substituierten benzolen, dadurch hergestelltes polymermaterial und sein verwendung
AU2003226956A1 (en) 2002-04-25 2003-11-10 Nkt Research And Innovation A/S Method and apparatus for plasma deposition of chemically reactive groups on substrates chemically reactive substrates obtainable by the method and use thereof
WO2004088710A2 (en) 2003-04-02 2004-10-14 Nkt Research & Innovation A/S Method and apparatus for gas plasma treatment with controlled extent of gas plasma, and use thereof
GB0406049D0 (en) 2004-03-18 2004-04-21 Secr Defence Surface coatings

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1102903A (en) * 1964-02-24 1968-02-14 Daikin Ind Ltd Fluoro alkyl-containing compounds and water- and oil-repellent compositions containing them
EP0049884A1 (de) 1980-10-11 1982-04-21 Daikin Kogyo Co., Ltd. Verfahren zur Erzeugung eines Fluoralkylacrylatpolymerfilmes auf einem Substrat und Verfahren zur Herstellung eines Resistbildes aus diesem Film
JPS57119906A (en) * 1981-01-19 1982-07-26 Daikin Ind Ltd Formation of smooth film on substrate
SU1158634A1 (ru) 1983-02-02 1985-05-30 Ивановский научно-исследовательский экспериментально-конструкторский машиностроительный институт Способ водо- и маслоотталкивающей отделки текстильных материалов
JPS59222340A (ja) * 1983-05-31 1984-12-14 大日本印刷株式会社 積層体
US5041304A (en) 1989-12-13 1991-08-20 Bridgestone Corporation Surface treatment method
JPH0816773A (ja) 1994-06-29 1996-01-19 Matsushita Electric Ind Co Ltd 画像処理方法

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
A. M. HYNES ET AL., MACROMOLECULES, vol. 29, 1996, pages 18 - 21
DATABASE WPI Week 8235, Derwent World Patents Index; AN 82-73505E, XP002079483 *
DATABASE WPI Week 8505, Derwent World Patents Index; AN 85-027803, XP002079484 *
H. YASUDA ET AL., J. POLYM. SCI., POLYM. CHEM. ED., vol. 15, 1977, pages 2411

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8852693B2 (en) 2011-05-19 2014-10-07 Liquipel Ip Llc Coated electronic devices and associated methods

Also Published As

Publication number Publication date
DE69842159D1 (de) 2011-04-14
PT2275598E (pt) 2015-02-06
USRE43651E1 (en) 2012-09-11
EP2275598B1 (de) 2014-12-17
GB9720078D0 (en) 1997-11-19
EP1557489A1 (de) 2005-07-27
GB9712338D0 (en) 1997-08-13
ES2357957T3 (es) 2011-05-04
EP1557489B1 (de) 2011-03-02
ATE500377T1 (de) 2011-03-15
DK2275598T3 (da) 2015-02-09
PT1557489E (pt) 2011-04-06
ES2530418T3 (es) 2015-03-02
DK1557489T3 (da) 2011-04-18

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