WO2006137726A2 - Revetement a faible adherence - Google Patents

Revetement a faible adherence Download PDF

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Publication number
WO2006137726A2
WO2006137726A2 PCT/NL2006/000300 NL2006000300W WO2006137726A2 WO 2006137726 A2 WO2006137726 A2 WO 2006137726A2 NL 2006000300 W NL2006000300 W NL 2006000300W WO 2006137726 A2 WO2006137726 A2 WO 2006137726A2
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WO
WIPO (PCT)
Prior art keywords
anyone
coating
fluorinated
polylactone
group
Prior art date
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Ceased
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PCT/NL2006/000300
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English (en)
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WO2006137726A3 (fr
Inventor
Tamara Dikic
Weihua Ming
Rudolfus Antonius Theodorus Maria Van Benthem
Gijsbertus De With
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Stichting Dutch Polymer Institute
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Stichting Dutch Polymer Institute
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Priority claimed from PCT/NL2005/000751 external-priority patent/WO2007046687A1/fr
Application filed by Stichting Dutch Polymer Institute filed Critical Stichting Dutch Polymer Institute
Publication of WO2006137726A2 publication Critical patent/WO2006137726A2/fr
Publication of WO2006137726A3 publication Critical patent/WO2006137726A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
    • C09D167/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
    • C08G18/4266—Polycondensates having carboxylic or carbonic ester groups in the main chain prepared from hydroxycarboxylic acids and/or lactones
    • C08G18/4269—Lactones
    • C08G18/4277—Caprolactone and/or substituted caprolactone
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
    • C08G18/46—Polycondensates having carboxylic or carbonic ester groups in the main chain having heteroatoms other than oxygen
    • C08G18/4607—Polycondensates having carboxylic or carbonic ester groups in the main chain having heteroatoms other than oxygen having halogens
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
    • C08G18/78—Nitrogen
    • C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
    • C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
    • C08G18/792—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
    • 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
    • C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
    • C09D167/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
    • C09D167/025—Polyesters derived from dicarboxylic acids and dihydroxy compounds containing polyether sequences
    • 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
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes
    • C09D175/06—Polyurethanes from polyesters

Definitions

  • the present invention relates to a coating of which the surface has a low adherence towards various contaminants. It also relates to the preparation of such a coating.
  • a coating comprising: a) a crosslinked polymeric network (N), based on a first polymer (P), b) a low-surface-energy group (E), coupled to the network N via c) a polymeric spacer (S), having the following relationship between the native surface energies of P, E, and S (resp. ⁇ p , ⁇ e , and ⁇ s , in mN/m): ⁇ e ⁇ ⁇ s ⁇ ⁇ p
  • the network N is provided with a so-called dangling chain (the polymeric spacer S), at the end of the chain being provided with a functional group, the low surface energy group E.
  • the self- replenishing low-adherence coatings have long functionalized dangling chains relatively homogeneously distributed (a gradient functional group concentration may still well exist) in a coating network.
  • the functionalized tails from sublayers will be able to reorient themselves to minimize the air/film interfacial energy (Scheme 1).
  • the approach is to control the diffusion of the functionalized species during film formation by, for instance, tuning the spacer length in the functionalized species, and adjusting the miscibility of P, E and S.
  • the synthesis of the network precursors is therefore of great importance, since the length, mobility, and miscibility of these chains have to be well controlled.
  • the term "native surface energy" of the respective groups in the coating refers to the surface energy of each individual group (P, E and S) in its separate form, i.e. before they are coupled to each other to form the coating. This native energy is measured according to the geometric mean method of Owens and Wendt (J. Appl. Polymer. Sci. (1969), 13, 1741 ).
  • each polymer is suitable, when it is crosslinkable into a polymeric network, as a result of which the dangling chains coupled thereon are restricted in their mobility.
  • P is selected from the group comprising polyurethane, polyester, polyether, polyetherester, and polyesterether.
  • each polymer P has the need of its own crosslinker, in order to become a crosslinked polymeric network N.
  • N is obtained via crosslinking of the polymer P with a crosslinker selected from the group comprising a polyisocyanate, a blocked polyisocyanate, a polycarbodiimide, a polyepoxide, or an alkylated melamine resin.
  • N is a polyurethane network based on a polylactone P, made of a lactone and a polyfunctional alcohol, and a polyisocyanate crosslinker.
  • the lactone for such a polyurethane based coating is caprolactone or an alkylsubstituted caprolactone (examples being 4-methylcaprolactone or 4-t-butylcaprolactone); and the polyfunctional alcohol is a trimethylol alkane, more preferred a trimethylol propane.
  • the functional group (E) at the end of the dangling chain (S) has to have a low native surface energy ( ⁇ s ). Preferably this ⁇ s has a value between 5 and 25 mN/m.
  • E low-surface-energy groups
  • E being selected from the group comprising a perfluoroalkyl, a perfluoropolyether, and a polysiloxane.
  • the native surface energy of E ( ⁇ e ) preferably has a value between 5 and 25 mN/m.
  • E is a perfluoroalkyl group
  • the perfluoroalkyl group there is a preference for the perfluoroalkyl group to be a perfluoro hexyl ethyl, or a perfluoro octyl ethyl group.
  • the polymeric spacer (S) has to have a certain length (or molecular weight).
  • S is a hydrocarbon based polymer having at least 10 C-atoms in the backbone. More preferred, S has a number-averaged molecular weight M n,s of between 200 and 10,000; preferably between 500 and 5,000. The molecular weights referred to are determined by gel permeation chromatography (GPC).
  • S has a glass transition temperature, which in general should not be below -150 0 C, and not above 75 0 C.
  • S has a glass transition temperature T g s (in 0 C) according to the following relation: -100 ⁇ T g,s ⁇ 50; preferably -60 ⁇ T g,s ⁇ 20.
  • S can be any polymer obeying the above referenced criteria. More preferred, S is selected from the group comprising polyurethane, polyester, polyether, polyetherester, and polyesterether. Preferably S is a polylactone; in its most preferred form a polycaprolactone.
  • the number-averaged molecular weight of S (M n,s ) is preferably between 200 and 10,000; the glass transition temperature of S (Tg, s ) is preferably between -100 and 50 0 C.
  • the coating of the present invention in general has a glass transition temperature (T g ⁇ C , in 0 C) of at least - ⁇ 40 0 C; more preferred T g , c has the following relation: -20 ⁇ T g ⁇ C ⁇ 50, even more preferred -10 ⁇ T g , 0 ⁇ 40. - A -
  • the coating has a relationship between the respective surface energies of: ⁇ e ⁇ ⁇ s ⁇ ⁇ p .
  • the relation is ⁇ ⁇ ⁇ ⁇ s ⁇ ⁇ p .
  • the coating has the following parameters:
  • the coating according to the present invention can, as described above, be based on different polymeric constituents.
  • a fluorine containing polyurethane coating will be described, as one of the embodiments of the present invention.
  • Such a process comprises the following steps: a) ring-opening polymerization of a first lactone with a perfluorinated alcohol, b) ring-opening polymerization of a second lactone with a di-, tri- or tetra hydroxyfunctional hydrocarbon, or its ether-derivative, c) crosslinking a mixture of the products obtained in step a) and step b) with a polyisocyanate crosslinker.
  • Ring-opening polymerization of lactones has been chosen to synthesize the precursors with well-defined structures (e.g. controlled molecular weight with a low molecular weight distribution index (PDI), functionality per polymer) in a controlled manner.
  • well-defined structures e.g. controlled molecular weight with a low molecular weight distribution index (PDI), functionality per polymer
  • the lactones can be any known in the art; preferably at least one of the lactones is ⁇ -caprolactone,.
  • the dangling chain, based on a perfluorinated alcohol preferably has, in its backbone, 6 - 20 C-atoms; more preferably said alcohol is selected from the group comprising perfluorohexyl ethanol, perfluorooctyl ethanol, or a mixture thereof.
  • the above mentioned polymeric spacer S with the low-surface-energy group E is formed; the product of this step a) should preferably have a number-averaged molecular weight (M n , a ) of between 1,000 and 4,000.
  • step b) the first polymer P is formed, which, after the crosslinking with a polyisocyanate based crosslinker, results in the crosslinked polymeric network N.
  • the products from the process steps a) and b) generally should have a PDI of at most 4.0; more preferred at most 2.5; and even more preferred at most 1. 5.
  • the molar ratio of the isocyanate and hydroxyl groups in the mixture of step c) is at least 1.0.
  • the present invention also relates to a coating comprising a fluorine containing crosslinked polyurethane.
  • Said fluorine containing crosslinked polyurethane can contain every desirable amount of fluorine.
  • the fluorine containing crosslinked polyurethane of the present invention comprises preferably up to 2.5 wt% of chemically bound fluorine.
  • the present invention also relates to a fluorinated polylactone, obtainable from a reaction between a lactone and a perfluorinated alcohol.
  • the lactone is ⁇ -caprolactone.
  • the perfluorinated alcohol has 6-12 C-atoms; more preferred the perfluorinated alcohol is either perfluorohexyl ethanol, perfluorooctyl ethanol, or a mixture thereof.
  • Said fluorinated polylactone is, as will be clear from the above, suitable as the building block for the combination of the spacer (S) with the terminal low-surface-energy group (E) in the coating of the invention.
  • the preferences for the precursors of the fluorinated polylactone i.e. the perfluorinated alcohol, and the lactone
  • the precursors of the fluorinated polylactone are already given above.
  • a process comprising a ring-opening polymerization of a lactone with a perfluorinated alcohol - use is made of the influence of a weak acid as a catalyst.
  • a weak acid is fumaric acid.
  • the temperature for such a preparation lies in general between room temperature and 150 0 C. Generally atmospheric pressure is applied, but, depending on the nature of the precursors, higher pressures can be applied.
  • the coating of the present invention can be applied to any type of substrate (metal, glass, etc.). It will generally be present in a thickniss of 10-100 ⁇ m. More preferably, said thickness is between 20-75 ⁇ m.
  • the coating of the present invention is very suitable as a so-called top-coat, in a system of a multilayer coating. This belongs to the general knowledge of the skilled man.
  • the invention will hereafter be elucidated by Examples. These Examples relate to a (process for the preparation of a) fluorinated coating. It is to be understood that variations in the three essential elements of the coating (i.e. the first polymer P, the low-surface-energy group E, and the polymeric spacer S) can be performed by the skilled man, following the teachings presented herein.
  • perfluoroalkyl alcohols perfluorohexyl ethanol (R f 6) and perfluorooctyl ethanol (R f 8), were supplied by Clariant GmbH (with trademarks of EA 600 and EA 800, respectively).
  • ⁇ -Caprolactone ( ⁇ -CL) was purchased from Acros Organics, 2-ethyl-2-(hydroxymethyl)-1 ,3-propanediol (TMP) from Merck, and fumaric acid from Sigma-Aldrich.
  • TMP 2-ethyl-2-(hydroxymethyl)-1 ,3-propanediol
  • a polyisocyanate crosslinker, Desmodur N3600 containing primarily the trimer of hexamethylenediisocyanate, was obtained from Bayer.
  • ⁇ -Caprolactone was dried with anhydrous MgSO 4 for 24 h and then vacuum distilled to remove water. Fumaric acid and the alcohols were dried in a vacuum oven at 40 0 C for 3 h before use. Solvents were used as received without further purification. 1 H NMR spectra were recorded on a Varian 400 spectrometer operating at 400.162 MHz at 25 0 C. CDCI 3 (with TMS as an internal standard) was used as a solvent. Melting and glass transition temperatures were determined on a Perkin Elmer Pyris 1 differential scanning calorimeter (DSC), with a heating/cooling rate of 10 °C/min. The onset temperature during the second heating run was taken as the melting point.
  • DSC Perkin Elmer Pyris 1 differential scanning calorimeter
  • MALDI-TOF MS measurements were preformed on a Voyager-DE Pro instrument (Perspective Biosystems, Framingham, MA). Polymers were dissolved in THF, and NaTFA or KTFA (Na- or K-trifluoroacetic acid) were used as the ionizing agent, lsotopic distribution calculations were preformed using DataExplorer Advanced Biosystems. Contact angle measurements were preformed on a Dataphysics OCA 30 Instruments, using deionized water and hexadecane (>99%, Merck) as probe liquids. Dynamic advancing contact angles were collected. SEC was carried out on a Waters SEC instrument equipped with a Waters Model 510 pump and a Model 410 refractive index detector (at 40 0 C).
  • the column used was PL2mixC, and THF (Biosolve, stabilised with BHT) was used as the eluent at a flow rate of 1.0 mL/min. Samples were filtered over a 13 mm x 0.2 ⁇ m PTFE filter (Alltech). Calibration was made using a universal calibration curve.
  • ⁇ -CL and alcohol were added to the flask in different molar ratios.
  • the molar ratio between ⁇ -CL and fumaric acid was kept at 10.
  • the synthesis was preformed under dry nitrogen atmosphere.
  • a typical procedure is as follows: a mixture of TMP and fumaric acid was heated to 90 0 C and then ⁇ -CL was added to the flask. The reaction mixture was stirred with a magnetic stirrer. After 24 h, it was diluted with THF 1 and the polymer was precipitated in n-heptane.
  • the formed precipitate was filtered off and washed with methanol (in the case of low MW PCL initiated by TMP, a mixture of water and methanol (1 :2) was used). White, sticky powder was, after washing, dried in vacuum at 40 0 C for 4 h.
  • Polyurethane coatings were prepared from a mixture of PCL precursors and a polyisocyanate crosslinker with either THF or N-methyl pyrrolidone (NMP) as a solvent. The molar ratio of NCO/OH was kept at 1.1. Films were applied on aluminum panels using a doctor blade driven by a 509 MC Coatmaster automatic film applicator. The films were then cured at 40 and 90 0 C when THF was used as the solvent, and at 125 0 C with NMP as the solvent.
  • NMP N-methyl pyrrolidone
  • Fumaric acid is a weak acid and activates monomer at rather high temperature for ring-opening polymerization; a long reaction time (e.g. 24 h) is usually needed for a complete polymerization, given that the primary polymerization pathway is through the activated monomer mechanism. For this reason, polymerization has a living character (shown later).
  • fumaric acid is insoluble in the monomer, and it acts as a heterogeneous catalyst. Good mixing of the reaction mixture is therefore important, especially if a high molecular mass is aimed in the experiment.
  • TMP-PCL For the PCL initiated by TMP (TMP-PCL), the area ratio of the signals z and k, A(H z )/A(H k ) is 2, which corresponds well to the molecular structure of TMP-PCL.
  • the number-average molecular weight of TMP-PCL is:
  • the area ratio of the signals d' and z, A(H rf )/A(H z ) is 1 , indicating that R f 6-PCL has a well defined structure with a perfluoroalkyl group at the one end of the chain and a hydroxyl group at the other end (further evidence is provided by MALDI TOF MS analysis below).
  • M n The number-averaged molecular weights (M n ) for fluorinated PCL and TMP-PCLs are shown in Table 1.
  • M n The number-averaged molecular weights
  • FIG. 4 A typical full MALDI mass spectrum for R f 8-PCL is given in Figure 4.
  • the sets of signals are separated by 114 Da ( Figure 4a), characteristic of the caprolactone repeating unit.
  • the molecular weights of individual main peaks correspond to the expected structure: (C 8 F 17 CH 2 CH 2 O-[C(O)-C 5 H 10 -O] n -H + Na ⁇ + .
  • MALDI TOF MS can be used as the quantitative technique for determining the average molecular weight of precursors. Average molecular weights determined by 1 H NMR, SEC and MALDI TOF MS for a number of samples are given in Table 1. As expected, PDI for all the samples (according to SEC below 1.2 and according to MALDI MS around 1.1) is low, which also indicates that PCLs initiated by TMP have similar numbers of monomer units per arm. Average molecular weights determined by MALDI MS and 1 H-NMR are in agreement. SEC measurement gave values that were significantly higher compared to the other two techniques. It has been shown from MALDI TOF MS and SEC that the targeted PCLs (controlled MW, low PDI, and controlled functionality) have been successfully synthesized, with the presence of only a minimal amount of water-initiated species.
  • Fluorinated PCLs of different molar masses were spin-cast from THF solutions (100 mg/1 mL of THF) on aluminum panels and then annealed in a vacuum oven at 60 0 C for 2 h. After annealing, contact angle measurements were performed on these films, using water and hexadecane as probe liquids. Both water and hexadecane contact angles were significantly higher comparing to those measured on the film of PCL initiated by butanol, indicating that fluorinated tails are preferentially enriched at the air-film interface. It can be seen from Figure 6 that a lower molecular mass of PCL chain facilitates the fluorine surface segregation, since the fluorine content is relatively higher and the chain mobility is enhanced when the molecular weight of the R f 8-PCL is low.
  • Crosslinked polyurethane films based on fluorinated PCLs The fluorinated and 3-armed PCL precursors were cured with a polyisocyanate crosslinker, Desmodur N3600, to prepare crosslinked polyurethane films with low surface energies.
  • the molar ratio of NCO/OH was maintained at 1.1.
  • the self-replenishing behavior of fluorinated tails was examined by angle-resolved X-ray photoelectron spectroscopy (XPS) in combination with microtoming.
  • the coating examined was prepared by casting the reaction mixture (R f 8- PCL, TMP-PCL, and Desmodur N3600) on a metal plate from NMP solution (50 wt% solid contents) and then curing at 120 0 C.
  • the coating was about 200 ⁇ m thick and contained 1 wt% of fluorine.
  • Thin slices of about 30 ⁇ m thick were cut by microtoming and the top surfaces of the slices were then examined by XPS.
  • Figure 9 F/C ratios at two different probe depths (4 and 8 nm) for thin slices cut from a polyurethane coating containing R f 8-PCL.
  • the F/C ratio appeared to be constant throughout the coating, indicating relatively homogeneous distribution of fluorinated species in the bulk of the film. What is significant is that, for each slice, the F/C ratio in the top 4 nm is about 60% greater than that in the top 8 nm of the slice. The greater F/C ratio in the top 4 nm clearly indicates that the replenishing of fluorinated tails already took place after the microtoming and before the XPS measurements; otherwise the F/C ratios in the top 4 and 8 nm would be the same for the slices from the bulk of the film. It is not surprising for the self-replenishing to take place at room temperature as far as the Tg (-20 0 C) of the coating is concerned.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Laminated Bodies (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

La présente invention a trait à un revêtement présentant une faible adhérence pour divers types de contaminants. Un tel revêtement contient un réseau polymère réticulé doté d'une chaîne pendante à extrémité fonctionnalisée, ce qui permet à la surface de conserver sa faible tension superficielle.
PCT/NL2006/000300 2005-06-21 2006-06-19 Revetement a faible adherence Ceased WO2006137726A2 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US69228105P 2005-06-21 2005-06-21
US60/692,281 2005-06-21
NLPCT/NL2005/000751 2005-10-19
PCT/NL2005/000751 WO2007046687A1 (fr) 2005-10-19 2005-10-19 Revetement a faible adherence

Publications (2)

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WO2006137726A2 true WO2006137726A2 (fr) 2006-12-28
WO2006137726A3 WO2006137726A3 (fr) 2007-03-29

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20140356998A1 (en) * 2013-05-28 2014-12-04 Samsung Display Co., Ltd. Donor substrate and method for forming transfer pattern using the same
US20160115275A1 (en) * 2008-02-26 2016-04-28 Total Research & Technology Feluy Monomers Issued From Renewable Resources and Process for Polymerising Them
CN110684455A (zh) * 2018-07-04 2020-01-14 富士施乐株式会社 表面保护树脂部件形成用溶液组和表面保护树脂部件
US10544260B2 (en) 2017-08-30 2020-01-28 Ppg Industries Ohio, Inc. Fluoropolymers, methods of preparing fluoropolymers, and coating compositions containing fluoropolymers

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3839937A1 (de) * 1988-11-26 1990-05-31 Henkel Kgaa Gleitlack fuer elastomerteile
DE4320527A1 (de) * 1992-06-22 1993-12-23 Whitaker Corp Elektrisch leitfähiges Gel
WO1996010595A1 (fr) * 1994-10-04 1996-04-11 Minnesota Mining And Manufacturing Company Compositions reactives de polyurethanne en deux parties et eventuellement revetements presentant une autoregeneration de la fissure et une resistance au rayage prepares a partir de ces compositions
EP1411073B1 (fr) * 2001-06-27 2013-03-20 Daikin Industries, Ltd. Composition d'agent de traitement de surface et procede de fabrication associe

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20160115275A1 (en) * 2008-02-26 2016-04-28 Total Research & Technology Feluy Monomers Issued From Renewable Resources and Process for Polymerising Them
US20140356998A1 (en) * 2013-05-28 2014-12-04 Samsung Display Co., Ltd. Donor substrate and method for forming transfer pattern using the same
US9099651B2 (en) * 2013-05-28 2015-08-04 Samsung Display Co., Ltd. Donor substrate and method for forming transfer pattern using the same
US9437819B2 (en) 2013-05-28 2016-09-06 Samsung Display Co., Ltd. Donor substrate and method for forming transfer pattern using the same
US10544260B2 (en) 2017-08-30 2020-01-28 Ppg Industries Ohio, Inc. Fluoropolymers, methods of preparing fluoropolymers, and coating compositions containing fluoropolymers
CN110684455A (zh) * 2018-07-04 2020-01-14 富士施乐株式会社 表面保护树脂部件形成用溶液组和表面保护树脂部件

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