WO2008083272A1 - Revêtements de polyurée et de polyuréthane résistants aux taches et à l'encrassement - Google Patents

Revêtements de polyurée et de polyuréthane résistants aux taches et à l'encrassement Download PDF

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Publication number
WO2008083272A1
WO2008083272A1 PCT/US2007/089037 US2007089037W WO2008083272A1 WO 2008083272 A1 WO2008083272 A1 WO 2008083272A1 US 2007089037 W US2007089037 W US 2007089037W WO 2008083272 A1 WO2008083272 A1 WO 2008083272A1
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trade designation
weight
under
coatings
fluorochemical
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PCT/US2007/089037
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English (en)
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Stephen E. Amos
Robert P. Messner
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3M Innovative Properties Company
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Publication of WO2008083272A1 publication Critical patent/WO2008083272A1/fr

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    • 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
    • C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
    • C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
    • C08G18/6666—Compounds of group C08G18/48 or C08G18/52
    • C08G18/667—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
    • C08G18/6681—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/32 or C08G18/3271 and/or polyamines of C08G18/38
    • C08G18/6685—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/32 or C08G18/3271 and/or polyamines of C08G18/38 with compounds of group C08G18/3225 or polyamines of C08G18/38
    • 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
    • C08G18/71—Monoisocyanates or monoisothiocyanates
    • C08G18/712—Monoisocyanates or monoisothiocyanates containing 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
    • C08G18/73—Polyisocyanates or polyisothiocyanates acyclic
    • 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
    • C09D175/02—Polyureas
    • 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
    • C08G2150/00—Compositions for coatings
    • C08G2150/50—Compositions for coatings applied by spraying at least two streams of reaction components
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K7/00—Use of ingredients characterised by shape
    • C08K7/22—Expanded, porous or hollow particles
    • C08K7/24—Expanded, porous or hollow particles inorganic
    • C08K7/28—Glass
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • C08L75/02—Polyureas

Definitions

  • the present invention relates to polyurea compositions and polyurethane compositions for forming coatings and coatings formed from such compositions.
  • the invention relates to stain and fouling resistant coatings, e.g., for use on rail cars, containers, vehicles, etc.
  • a developing energy source is oil from oil sands and tar sands. Such sands tend to stick to equipment and vehicles used to move and process them. As a result, efficiency is reduced as the deposits build up, increasing the weight of moving vehicles, clogging handling chutes, etc. It is common practice today to remove vehicles used in such operations from service for one or two days each week for extensive spray washing to remove the build up of deposits from the vehicle in addition to an extensive solvent wash done on a monthly basis.
  • An established energy source is coal which is mined in one location and then shipped to another location via such means as rail car. When removed from the mine, coal commonly contains significant water content and has a temperature of about 40 to about 50 0 F (4 to 10 0 C).
  • the present invention provides novel polyurethane compositions and polyurea compositions and novel coatings formed therefrom, and transporters, e.g., carriers, vessels, and vehicles, having such coatings thereon.
  • compositions of the invention comprise reactive precursors for forming a polyurethane or polyurea coating and at least one fluorochemical fluorochemical compound.
  • compositions of the invention can be applied in convenient manner, e.g., spraying, to form films or coatings on substrates.
  • the resultant films or coatings can exhibit exceptional physical properties such as high hardness, flexibility, abrasion resistance, and chemical resistance.
  • Durable and light weight, films and coatings of the invention exhibit oil-repellency, water-repellency, and stain resistance.
  • the invention provides polyurethane and polyurea coatings that provide heretofore unattainable resistance to staining and fouling.
  • compositions of the invention comprise reactive precursors for forming polyurethane and/or polyureas and at least one fluorochemical compound.
  • the fluorochemical compound is reactive with one or more of the reactive precursors.
  • Polyurethanes can be prepared by reacting one or more isocyanates with one or more polyols.
  • Polyureas can be prepared by reacting one or more isocyanates with one or more amines.
  • fluorochemical compounds suitable for use herein include the fluorochemical monoisocyanates disclosed in U.S. Patent No. 7,081,545 (Klun et al.) which is incorporated herein by reference in its entirety.
  • Fluorochemical alcohols that are useful starting compounds include C 2 F 5 SO 2 NCH 3 (CH 2 ) 2 OH, C 2 F 5 SO 2 NCH 3 (CH 2 ) 3 OH, C 2 F 5 SO 2 NCH 3 (CH 2 ) 4 OH, C 3 F 7 S ⁇ 2 NCH 3 (CH 2 ) 2 ⁇ H, C 3 F 7 SO 2 NCH 3 (CH 2 ) 3 OH, C 3 F 7 SO 2 NCH 3 (CH 2 )4 ⁇ H, C 4 F 9 SO 2 NCH 3 (CH 2 ) 2 OH, C 4 F 9 SO 2 NCH 3 (CH 2 ) 3 OH, C 4 F 9 SO 2 NCH 3 (CH 2 ) 4 OH, C 5 FnSO 2 NCH 3 (CH 2 ) 2 OH, C 5 FnSO 2 NCH 3 (CH 2 ) 3 OH, C 5 Fi iSO 2 NCH 3 (CH 2 ) 4 ⁇ H, and mixtures thereof.
  • Preferred fluorochemical alcohols include, for example, C 2 F 5 SO 2 NCH 3 (CH 2 ) 2 OH, C 4 F 9 SO 2 NCH 3 (CH 2 ) 2 OH, C 4 F 9 SO 2 NCH 3 (CH 2 ) 4 OH, and mixtures thereof. More preferred fluorochemical alcohols include, for example, C 4 F 9 SO 2 NCH 3 (CH 2 ) 2 OH, C 4 F 9 SO 2 NCH 3 (CH 2 ) 4 OH, and mixtures thereof. A most preferred fluorochemical alcohol is C 4 F 9 SO 2 NCH 3 (CH 2 ) 2 OH.
  • Useful fluorochemical alcohols can be purchased from 3M (St. Paul, MN), or can be prepared essentially as described in U.S.
  • the above-described fluorochemical alcohols can be reacted with 4,4'- diphenylmethane diisocyanate in a solvent to form the corresponding monoisocyanates.
  • 4,4'-Diphenylmethane diisocyanate is commonly known as "methylene diisocyanate" or "MDI".
  • MDI is commercially available as ISONATETM 125M from the Dow Chemical Company (Midland, MI), and as MONDURTM M from Bayer Polymers (Pittsburgh, PA).
  • the process of the invention can be carried out with a molar ratio of fluorochemical alcohol:MDI from about 1 : 1 to about 1 :2.5.
  • the molar ratio of fluorochemical alcohol :MDI is from about 1 : 1 to about 1 :2. More preferably, the molar ratio is from about 1 : 1.1 to about 1 : 1.5.
  • the process of the invention can be carried out in a solvent in which the resulting monoisocyanate is not soluble (that is, the solvent is one in which the monoisocyanate partitions out of so that it no longer participates in the reaction).
  • the solvent is a nonpolar solvent. More preferably, it is a nonpolar non-aromatic hydrocarbon or halogenated solvent.
  • useful solvents include cyclohexane, n-heptane, hexanes, n- hexane, pentane, n-decane, /-octane, octane, methyl nonafluoroisobutyl ether, methyl nonafluorobutyl ether, petroleum ether, and the like, and mixtures thereof.
  • a mixture of methyl nonafluoroisobutyl ether and methyl nonafluorobutyl ether is available as HFE- 7100 NOVECTM Engineered Fluid from 3M.
  • Preferred solvents include, for example, methyl nonafluoroisobutyl ether, methyl nonafluorobutyl ether, petroleum ether, n- heptane, and the like.
  • the solvent has a Hildebrand solubility parameter ( ⁇ ) of less than about 8.3 (cal/cm 3 ) 1/2 (about 17 MPa 1/2 ) and a hydrogen bonding index of less than about 4.
  • the Hildebrand solubility parameter is a numerical value that indicates the relative solvency behavior of a specific solvent. It is derived from the cohesive energy density (c) of the solvent, which in turn is derived from the heat of vaporization:
  • T temperature
  • V m molar volume
  • n-heptane has a Hildebrand solubility index of about 7.4 (cal/cm 3 ) 1/2 (about 15 MPa 1/2 ), and water has a Hildebrand solubility index of about 23.4 (cal/cm 3 ) i/2 (about 48 MPa l/2 ) (Principles of Polymer Systems. 2 nd edition, McGraw-Hill Book Company, New York (1982)).
  • the hydrogen bonding index is a numerical value that indicates the strength of the hydrogen bonding that occurs in a solvent. Hydrogen bonding values range from -18 to +15. For example, n-heptane has a hydrogen bonding value of about 2.2, and water has a hydrogen bonding value of about 16.2 (Principles of Polymer Systems, 2 nd edition, McGraw-Hill Book Company, New York (1982)).
  • the reaction can be carried out by combining the fluorochemical alcohol and MDI in the solvent.
  • the fluorochemical alcohol is added to MDI, which is in the solvent, over time.
  • the fluorochemical alcohol can first be dissolved in a solvent such as, for example, toluene, and then added to the MDI in solution.
  • the reaction mixture is agitated.
  • the reaction can generally be carried out at a temperature between about 25 0 C and about 7O 0 C (preferably, between about 25 0 C and about 5O 0 C).
  • the reaction can be carried out in the presence of a catalyst.
  • Useful catalysts include bases (for example, tertiary amines, alkoxides, and carboxylates), metal salts and chelates, organometallic compounds, acids, and urethanes.
  • the catalyst is an organotin compound (for example, dibutyltin dilaurate (DBTDL)) or a tertiary amine (for example, diazobicyclo[2.2.2]octane (DABCO)), or a combination thereof. More preferably, the catalyst is DBTDL.
  • the reaction product can be filtered out and dried.
  • the reaction product typically comprises greater than about 85% of the desired fluorochemical monoisocyanate (preferably, greater than about 90%; more preferably, greater than about 95%).
  • Fluorochemical monoisocyanates that can be prepared using the process of the invention can be represented by the following formula:
  • Preferred fluorochemical monoisocyanates that can be prepared using the process of the invention include, for example:
  • More preferred fluorochemical monoisocyanates prepared using the process of the invention include, for
  • Fluorochemical monoisocyanates prepared using the process of the invention can be useful starting compounds in processes for preparing fluorinated acrylic polymers with water- and oil-repellency properties.
  • fluorochemical monoisocyanates prepared using the process of the invention can be reacted with active hydrogen-containing compounds, materials, or surfaces bearing hydroxyl, primary or secondary amines, or thiol groups.
  • the monomer produced by reacting a fluorochemical monoisocyanate prepared by the process of the invention with a hydroxy alkyl acrylate such as hydroxy ethyl acrylate, for example, can be polymerized (alone or with comonomers) to provide polymers that have useful water- and oil-repellency properties.
  • compositions of the invention will further comprise filler materials such as glass microspheres, glass bubbles, ceramic microspheres, or other particles.
  • coatings of the invention can be used as coatings on motor vehicle bodies, undercarriages, truck beds, carriers and vessels used for transporting materials, etc.
  • the coatings exhibit good adhesion to metal substrates coupled with oil-repellency, water- repellency, and stain resistance.
  • An illustrative application of the compositions and coatings of the invention is on equipment and vehicles used in mining operations, e.g., for oil sands and tar sands. Despite the tendency of such sands to stick to equipment and vehicles used to move and process them, use of coatings of the invention will reduce the maintenance time required to clean conventional equipment and vehicles, thereby reducing downtime and increasing efficiency of operations.
  • Coatings of the invention preferably contain glass microspheres and or bubbles to impart improved insulative properties (e.g., thermal insulation, noise dampening, vibration, etc.), reduce effective weight of the coating.
  • coatings of the invention are made in combination with open celled, foamed construction.
  • Coatings of invention can be made with superior abrasion resistance and hardness.
  • compositions of invention can be applied by any of a variety of techniques.
  • compositions of the invention can be applied by such convenient techniques as spraying.
  • Coatings of the invention can applied over other, less durable insulation materials to provide optimized, composite properties.
  • the present invention may be used to provide a polyurea insulation coating sprayed over other insulation materials such as polystyrene or polyurethane open cell foam insulation, or other insulative material.
  • Films and coatings of the invention may be used in conjunction with other materials and layers to make multilayer composite constructions offering desired performance.
  • Compositions of the invention can be coated over blast and tear resistant films to impart improved blast and/or projectile resistance.
  • compositions and coatings of the invention make them well suited for a wide variety of applications.
  • Some examples include protective coatings to protect the cab, passenger compartment, load area, or other chambers of vehicles including aircraft, watercraft and land vehicles.
  • the invention provides advantageous results on wheeled and tracked vehicles, e.g., trucks, HUMVEEs, tanks, etc. , airplanes, space vehicles, helicopters, boats and other enclosed cockpit vehicles, from heat from engines or ambient sources.
  • protective coatings on equipment and vehicles or vehicle components that are used in extreme environments, e.g., trucks, tanks, airplanes, space vehicles, helicopters, boats, pipes, bridges, off-shore oil platforms, and other metallic substrates used in extreme environments or washed with bleach and other corrosive materials to provide corrosion resistance for the metal substrates.
  • the invention can be used on a variety of materials handling equipment including wheelbarrows, pipelines, sluices, etc. Examples
  • the treated substrates were tested for their contact angles versus water using an Olympus TGHM goniometer (Olympus Corp, Pompano Beach, Florida). Contact angles were measured at least 24 hrs after cure. The values are the mean values of 4 measurements and are reported in degrees. The minimum measurable value for a contact angle was 20. A value less than 20 means that the liquid spreads on the surface.
  • a 4 inch X 6 inch (10.16 cm X 15.24 cm) rectangular hole was cut in the top of a lab furnace (Econo-Kiln, Model K 14, L & L Manufacturing Co., Twin Oaks, Pennsylvania; maximum temperature of 1832°F (1000 0 C)).
  • the sample to be tested was placed over the rectangular hole in the furnace such that the edges of the sample fully overlapped on all sides of the opening.
  • Two thermocouples Type K Thermocouple
  • Thermometer Model 650, Omega Engineering, Inc., Stamford, Connecticut
  • One thermocouple measures the external face temperature (Tom s i de ) of the sample (that portion outside the oven) and one thermocouple measures the internal face temperature Ti ns jd e of the sample (that portion inside the furnace).
  • the furnace oven was turned on and the T 1n , ⁇ of the sample was adjusted to 200°F (93.3°C). After several minutes, the Toutside was recorded.
  • Model ThermaCAMTM P65 infrared camera available from Flir Systems Inc., Portland, Oregon, was used to analyze the temperature of the external face surface of the sample.
  • Part A and Part B A two component polyurea was formulated as follows.
  • Part A contained hexamethylene diisocyanate (85.2% by weight, obtained from Rhodia, Inc., Cranbury, New Jersey, under the trade designation "TOLONATETM HDT LV2”), glass microspheres (13.5 % by weight, obtained from 3M Company under the trade designation "3MTM GLASS MICROSPHERES K37”) and a modified polyurea (1.3% by weight, obtained from BYK Chemie, Wesel, Germany, under the trade designation "BYKTM 410” ).
  • hexamethylene diisocyanate 85.2% by weight, obtained from Rhodia, Inc., Cranbury, New Jersey, under the trade designation "TOLONATETM HDT LV2”
  • glass microspheres (13.5 % by weight, obtained from 3M Company under the trade designation "3MTM GLASS MICROSPHERES K37”
  • a modified polyurea (1.3% by weight, obtained from BYK Chemie,
  • Part B contained diethyltoluenediamine (32.4% by weight, obtained from Albemarle Corporation, Bayport, Texas, under the trade designation “ETHACURETM 100"), polyoxypropylenediamine (39.6% by weight, obtained from Huntsman Corporation, Salt Lake City, Utah under the trade designation "JEFF AMINETM D-2000” ), an aromatic secondary diamine (6.5% by weight, obtained from UOP, A Honeywell Company, Tonawanda, New York, under the trade designation "UNILINKTM 4200”), a trifunctional amine (2.4% by weight, obtained from Huntsman Corporation under the trade designation "JEFF AMINETM T-5000"), glass microspheres (18.2% by weight, obtained from 3M Company under the trade designation "3MTM GLASS MICROSPHERES K37”), a modified polyurea (0.8% by weight, obtained from BYK Chemie, under the trade designation "BYKTM 410”) and a liquid organic pigment to produce the desired color (0.1%).
  • Parts A and B were sprayed from a plural component proportioning sprayer (obtained from Graco, Minneapolis, Minnesota, under the trade designation "REACTOR H-XP2" using a "FUSION MP” spray gun with nozzles. Each part (A and B) was kept separate until they exited the spray gun. The two components, A and B, were stirred, in separate pots, in the spray unit and maintained at a temperature of 16O 0 F (71 0 C) during the spray process. The materials (Parts A and B) were sprayed on to a cold roll steel panel that was previously sprayed with a release agent (from Sierra Paint Co., Minnetonka, Minnesota, under the trade designation "TK-709 UR”) and also waxed paper. The formulation cured within about 20 seconds. After a period of time the sprayed panels were peeled from the metal substrate and waxed paper and tested as described above. The contact angle data is listed in Table 1. Thermal conductivity data is listed in Table 2.
  • Part A and Part B A two component polyurea was formulated as follows.
  • Part A contained hexamethylene diisocyanate (85.2% by weight, obtained from Rhodia, Inc., Cranbury, New Jersey, under the trade designation "TOLONATETM HDT LV2”), glass microspheres (13.5 % by weight, obtained from 3M Company under the trade designation "3MTM GLASS MICROSPHERES K37”) and a modified polyurea (1.3% by weight, obtained from BYK Chemie, Wesel, Germany, under the trade designation "BYKTM 410” ).
  • hexamethylene diisocyanate 85.2% by weight, obtained from Rhodia, Inc., Cranbury, New Jersey, under the trade designation "TOLONATETM HDT LV2”
  • glass microspheres (13.5 % by weight, obtained from 3M Company under the trade designation "3MTM GLASS MICROSPHERES K37”
  • a modified polyurea (1.3% by weight, obtained from BYK Chemie,
  • Part B contained diethyltoluenediamine (31.6% by weight, obtained from Albemarle Corporation, Bayport, Texas, under the trade designation “ETHACURE 100"), polyoxypropylenediamine (38.7% by weight, obtained from Huntsman Corporation, Salt Lake City, Utah, under the trade designation "JEFF AMINETM D-2000” ), an aromatic secondary diamine (6.3% by weight, obtained from UOP, A Honeywell Company, Tonawanda, New York under the trade designation "UNILINKTM 4200”), a trifunctional amine (2.4% by weight, obtained from Huntsman Corporation under the trade designation "JEFFAMINETM T-5000"), glass microspheres (17.8% by weight, obtained from 3M Company under the trade designation "3MTM GLASS MICROSPHERES K37”), a modified polyurea (0.7% by weight, obtained from BYK Chemie, under the trade designation "BYKTM 410”), deionized water (2.4% by weight) and a liquid organic pigment to produce the desired color (
  • Parts A and B were sprayed from a plural component proportioning sprayer (obtained from Graco, Minneapolis, Minnesota, under the trade designation "REACTOR H-XP2" using a "FUSION MP” spray gun with nozzles. Each part (A and B) was kept separate until they exited the spray gun. The two components, A and B, were stirred, in separate pots, in the spray unit and maintained at a temperature of 16O 0 F (71 0 C) during the spray process. The materials (Parts A and B) were sprayed on to a cold roll steel panel that was previously sprayed with a release agent (from Sierra Paint Co., Minnetonka, Minnesota, under the trade designation "TK-709 UR”) and also waxed paper. The formulation cured within about 20 seconds. After a period of time the sprayed panels were peeled from the metal substrate and waxed paper. The contact angle data is listed in Table 1. Thermal conductivity data is listed in Table 2.
  • Part A and Part B A two component polyurea (Part A and Part B) was formulated as follows.
  • Part A contained hexamethylene diisocyanate (84.4% by weight, obtained from Rhodia, Inc., Cranbury, New Jersey, under the trade designation "TOLONATETM HDT LV2”), glass microspheres (12.3 % by weight, obtained from 3M Company under the trade designation "3MTM GLASS MICROSPHERES K37”), a modified polyurea (1.3% by weight, obtained from BYK Chemie, Wesel, Germany, under the trade designation "BYKTM 410” ) and a fluorochemical urethane (2% by weight, obtained from 3M Company under the trade designation "SRC-220".
  • hexamethylene diisocyanate 84.4% by weight, obtained from Rhodia, Inc., Cranbury, New Jersey, under the trade designation "TOLONATETM HDT LV2”
  • glass microspheres (12.3 % by weight, obtained from 3M Company under the trade
  • Part B contained diethyltoluenediamine (32.4% by weight, obtained from Albemarle Corporation, Bayport, Texas, under the trade designation “ETHACURETM 100"), polyoxypropylenediamine (39.6% by weight, obtained from Huntsman Corporation, Salt Lake City, UT under the trade designation "JEFF AMINETM D-2000” ), an aromatic secondary diamine (6.5% by weight, obtained from UOP, A Honeywell Company, Tonawanda, New York under the trade designation "UNILINKTM 4200”), a trifunctional amine (2.4% by weight, obtained from Huntsman Corporation under the trade designation "JEFFAMINETM T-5000"), glass microspheres (18.2% by weight, obtained from 3M Company under the trade designation "3MTM GLASS MICROSPHERES K37”), a modified polyurea (0.8% by weight, obtained from BYK Chemie, under the trade designation "BYKTM 410”), and a liquid organic pigment to produce the desired color (0.1 %).
  • Parts A and B were sprayed from a plural component proportioning sprayer (obtained from Graco, Minneapolis, MN, under the trade designation "REACTOR H- XP2" using a "FUSION MP” spray gun with nozzles. Each part (A and B) was kept separate until they exited the spray gun. The two components, A and B, were stirred, in separate pots, in the spray unit and maintained at a temperature of 16O 0 F (71 0 C) during the spray process. The materials (Parts A and B) were sprayed on to a cold roll steel panel that was previously sprayed with a release agent (from Sierra Paint Co., Minnetonka, MN, under the trade designation "TK-709 UR”) and also waxed paper. The formulation cured within about 20 seconds. After a period of time the sprayed panels were peeled from the metal substrate and waxed paper and tested as described above. The data is listed in Table 1.
  • Part A and Part B A two component polyurea (Part A and Part B) was formulated as follows.
  • Part A contained hexamethylene diisocyanate (76.8% by weight, obtained from Rhodia, Inc., Cranbury, New Jersey, under the trade designation "TOLONATETM HDT LV2”), glass microspheres ( 12.2 % by weight, obtained from 3M Company under the trade designation "3MTM GLASS MICROSPHERES K37”), a modified polyurea (1.0% by weight, obtained from BYK Chemie, Wesel, Germany, under the trade designation "BYK 410” ) and a fluorochemical urethane (10% by weight, obtained from 3M Company under the trade designation "SRC-220".
  • Part B contained diethyltoluenediamine (32.4% by weight, obtained from Albemarle Corporation, Bayport, TX, under the trade designation
  • ETHACURETM 100 polyoxypropylenediamine (39.6% by weight, obtained from Huntsman Corporation, Salt Lake City, UT under the trade designation "JEFF AMINETM D-2000” ), an aromatic secondary diamine (6.5% by weight, obtained from UOP, A Honeywell Company, Tonawanda, New York, under the trade designation “UNILINKTM 4200”), a trifunctional amine (2.4% by weight, obtained from Huntsman Corporation under the trade designation "JEFF AMINETM T-5000”), glass microspheres (18.2% by weight, obtained from 3M Company under the trade designation "3MTM GLASS MICROSPHERES K37”), a modified polyurea (0.8% by weight, obtained from BYK Chemie, under the trade designation "BYKTM 410”), and a liquid organic pigment to produce the desired color (0.1 %).
  • Parts A and B were sprayed from a plural component proportioning sprayer (obtained from Graco, Minneapolis, Minnesota, under the trade designation "REACTOR H-XP2" using a "FUSION MP” spray gun with nozzles. Each part (A and B) was kept separate until they exited the spray gun. The two components, A and B, were stirred, in separate pots, in the spray unit and maintained at a temperature of 16O 0 F (71 0 C) during the spray process. The materials (Parts A and B) were sprayed on to a cold roll steel panel that was previously sprayed with a release agent (from Sierra Paint Co., Minnetonka, Minnesota, under the trade designation "TK-709 UR”) and also waxed paper. The formulation cured within about 20 seconds. After a period of time the sprayed panels were peeled from the metal substrate and waxed paper and tested as described above. The data is listed in Table 1.
  • Part A and Part B A two component polyurea was formulated as follows.
  • Part A contained hexamethylene diisocyanate (81.8% by weight, obtained from Rhodia, Inc., Cranbury, New Jersey, under the trade designation "TOLONATETM HDT LV2”), glass microspheres (13.0 % by weight, obtained from 3M Company under the trade designation "3MTM GLASS MICROSPHERES K37"), a modified polyurea (1.2% by weight, obtained from BYK Chemie, Wesel, Germany, under the trade designation "BYKTM 410” ) and a fluorochemical monoisocyanate (4% by weight, as prepared in U.S. Pat. No.
  • Part B contained diethyltoluenediamine (32.4% by weight, obtained from Albemarle Corporation, Bayport, Texas, under the trade designation "ETHACURETM 100"), polyoxypropylenediamine (39.6% by weight, obtained from Huntsman Corporation, Salt Lake City, Utah under the trade designation "JEFFAMINETM D-2000” ), an aromatic secondary diamine (6.5% by weight, obtained from UOP, A Honeywell Company, Tonawanda, New York, under the trade designation "UNILINKTM 4200”), a trifunctional amine (2.4% by weight, obtained from Huntsman Corporation under the trade designation "JEFFAMINETM T-5000"), glass microspheres (18.2% by weight, obtained from 3M Company under the trade designation "3MTM GLASS MICROSPHERES K37”), a modified polyurea (0.8% by weight, obtained from BYK Chemie,
  • Parts A and B were sprayed from a plural component proportioning sprayer (obtained from Graco, Minneapolis, Minnesota, under the trade designation "REACTOR H-XP2" using a "FUSION MP” spray gun with nozzles. Each part (A and B) was kept separate until they exited the spray gun. The two components, A and B, were stirred, in separate pots, in the spray unit and maintained at a temperature of 16O 0 F (71 0 C) during the spray process. The materials (Parts A and B) were sprayed on to a cold roll steel panel that was previously sprayed with a release agent (from Sierra Paint Co., Minnetonka, Minnesota, under the trade designation "TK-709 UR”) and also waxed paper. The formulation cured within about 20 seconds. After a period of time the sprayed panels were peeled from the metal substrate and waxed paper and tested as described above. The data is listed in Table 1.

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

Abstract

L'invention concerne des installations de transport, par exemple installations de transport de minerai, véhicules, matériel de manipulation de matières, entre autres, ayant sur ceux-ci des revêtements de polyurée fluorée et de polyuréthane fluoré.
PCT/US2007/089037 2006-12-29 2007-12-28 Revêtements de polyurée et de polyuréthane résistants aux taches et à l'encrassement WO2008083272A1 (fr)

Applications Claiming Priority (2)

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US88279006P 2006-12-29 2006-12-29
US60/882,790 2006-12-29

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GB2466501B (en) * 2008-12-23 2012-11-28 Isothane Ltd Method for preparing a composite material
US20110052874A1 (en) * 2009-07-02 2011-03-03 Wensheng Zhou Roofing articles with highly reflective coated granules
WO2011082374A1 (fr) 2009-12-31 2011-07-07 Firestone Building Products Company, Llc Membrane asphaltique comprenant des granules contenant de la mullite
CA2948169A1 (fr) 2016-11-09 2018-05-09 Fccl Partnership Appareil de transport d'hydrocarbures visqueux
WO2019118636A1 (fr) 2017-12-13 2019-06-20 Donaldson Company, Inc. Fibres fines de polyamide oléophobes, procédés, supports de filtre et éléments filtre

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6077609A (en) * 1997-06-27 2000-06-20 Dyneon Llc Composite articles including fluoropolymers and non-fluorinated polymers and method for making the same
US6117508A (en) * 1997-06-27 2000-09-12 Dyneon Llc Composite articles including a fluoropolymer blend
US6346328B1 (en) * 1998-07-30 2002-02-12 Dyneon Llc Composite articles including a fluoropolymer

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2803656A (en) * 1956-01-23 1957-08-20 Minnesota Mining & Mfg Fluorocarbonsulfonamidoalkanols and sulfates thereof
US4001305A (en) * 1974-02-04 1977-01-04 Ciba-Geigy Corporation Rf-glycols containing two perfluoroalkylthio groups and useful compositions therefrom
EP1246856B1 (fr) * 1999-10-27 2009-07-15 3M Innovative Properties Company Composes fluores sulfonamides tensioactifs
US7081545B2 (en) * 2003-12-31 2006-07-25 3M Innovative Properties Company Process for preparing fluorochemical monoisocyanates

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6077609A (en) * 1997-06-27 2000-06-20 Dyneon Llc Composite articles including fluoropolymers and non-fluorinated polymers and method for making the same
US6117508A (en) * 1997-06-27 2000-09-12 Dyneon Llc Composite articles including a fluoropolymer blend
US6346328B1 (en) * 1998-07-30 2002-02-12 Dyneon Llc Composite articles including a fluoropolymer

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