WO2014047018A2 - Compositions de revêtement et articles préparés à partir de celles-ci - Google Patents

Compositions de revêtement et articles préparés à partir de celles-ci Download PDF

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Publication number
WO2014047018A2
WO2014047018A2 PCT/US2013/060026 US2013060026W WO2014047018A2 WO 2014047018 A2 WO2014047018 A2 WO 2014047018A2 US 2013060026 W US2013060026 W US 2013060026W WO 2014047018 A2 WO2014047018 A2 WO 2014047018A2
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WO
WIPO (PCT)
Prior art keywords
composition
coating composition
coating
diisocyanate
aliphatic isocyanate
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/US2013/060026
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English (en)
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WO2014047018A3 (fr
Inventor
Rajan B. BODKHE
Alexander J. KUGEL
Leon Levitt
Craig M. MOSS
Michael A. Johnson
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3M Innovative Properties Co
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3M Innovative Properties Co
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Publication of WO2014047018A2 publication Critical patent/WO2014047018A2/fr
Publication of WO2014047018A3 publication Critical patent/WO2014047018A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/71Monoisocyanates or monoisothiocyanates
    • C08G18/715Monoisocyanates or monoisothiocyanates containing sulfur in addition to isothiocyanate sulfur
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08Processes
    • C08G18/10Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30Low-molecular-weight compounds
    • C08G18/302Water
    • C08G18/307Atmospheric humidity
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40High-molecular-weight compounds
    • C08G18/42Polycondensates having carboxylic or carbonic ester groups in the main chain
    • C08G18/44Polycarbonates
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72Polyisocyanates or polyisothiocyanates
    • C08G18/74Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/75Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
    • C08G18/751Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
    • C08G18/752Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
    • C08G18/753Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
    • C08G18/755Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72Polyisocyanates or polyisothiocyanates
    • C08G18/77Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
    • C08G18/78Nitrogen
    • C08G18/79Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
    • C08G18/791Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
    • C08G18/792Nitrogen 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
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72Polyisocyanates or polyisothiocyanates
    • C08G18/80Masked polyisocyanates
    • C08G18/8061Masked polyisocyanates masked with compounds having only one group containing active hydrogen
    • C08G18/807Masked polyisocyanates masked with compounds having only one group containing active hydrogen with nitrogen containing compounds
    • C08G18/808Monoamines
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING 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
    • C09D175/00Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04Polyurethanes
    • C09D175/06Polyurethanes from polyesters

Definitions

  • the present disclosure relates to coating compositions.
  • the present disclosure also relates to articles and films made using the coating compositions.
  • the present disclosure further relates to a method for preventing water vapor transport across a surface of a structure using the coating compositions.
  • Air barrier systems control movement of air, and specifically water vapor, across a surface of a structure, such as a building enclosure. In exterior walls, uncontrolled air flow is the greatest source of moisture and condensation damage. Indoor comfort is affected by air temperature, relative humidity, direction of airflow and surrounding surface temperatures. Indoor air quality is enhanced by air barrier systems by keeping pollutants out of building interiors and is an efficient way of keeping pollutants out.
  • Air barrier systems have significant impact on electricity consumption and gas bills. Air barrier systems in nonresidential buildings are estimated to reduce air leakage by up to 83 percent, saving on gas bill more than 40 % and reducing electricity consumption more than 25% according to simulations by the National Institute of Standards and Technology (NIST) of typical buildings without air barriers. Water vapor is a key ingredient in corrosion and mold growth. Air barrier systems help prevent water vapor from being transported by air movement between exteriors and interiors of structures, such as buildings.
  • the present disclosure provides a coating composition
  • a coating composition comprising a one-part moisture-curable polyurethane comprising a polycarbonate back bone and at least one end group derived from an aliphatic isocyanate; and a liquid hydrocarbon resin, where the liquid hydrocarbon resin is non- reactive with the at least one end group derived from an aliphatic isocyanate.
  • the coating composition is a liquid at ambient conditions.
  • the coating composition comprises at least 10 wt% of components (a) and (b) based on the total weight of the coating composition.
  • the liquid hydrocarbon resin comprises a polyisobutene.
  • the coating composition further comprises fillers.
  • the one-part moisture-curable polyurethane further comprises an aliphatic isocyanate trimer. In some embodiments, the one -part moisture-curable polyurethane further comprises a bis(oxazolidine)-based moisture-triggered isocyanate.
  • the one-part moisture-curable polyurethane further comprises a second end group derived from an aliphatic isocyanate.
  • the aliphatic isocyanate can be derived, in some embodiments, from ethylene diisocyanate; 1 ,4-tetramethylene diisocyanate; 1,6-hexamethylene diisocyanate; 2,2,4-trimethyl- 1,6-hexamethylene diisocyanate; 1, 12-dodecamethylene diisocyanate; 1- isocyanato-3-isocyanatomethyl-3,5,5-trimethyl-cyclohexane; bis-(4-isocyanatocyclohexyl)methane; bis- (4-isocyanato-3-methyl-cyclohexyl)methane; isophorone diisocyanate; dimer diisocyanate; m- tetramethylxylene diisocyanate; and combinations thereof.
  • the end groups are different.
  • the present disclosure provides an article comprising a substrate coated with a coating comprising any of the presently disclosed coating compositions.
  • the coating is continuous.
  • the present disclosure provides a film comprising the presently disclosed coating composition.
  • the film has a permeability of less than 1 perms according to ASTM E 96.
  • the present disclosure provides a method of coating a substrate surface comprising applying the presently disclosed coating composition to a substrate surface and allowing it to cure.
  • the coating composition is applied at an ambient temperature of -20°C or higher.
  • the present disclosure provides a method for preventing water vapor transport across a surface of a structure comprising (a) coating at least a portion of the surface of the structure with a coating composition comprising: a one-part moisture-curable polyurethane comprising a polycarbonate back bone and at least one end group derived from an aliphatic isocyanate; and a liquid hydrocarbon resin, wherein the liquid hydrocarbon resin is non-reactive with the at least one end group derived from an aliphatic isocyanate; and (b) curing the coating composition.
  • a coating composition comprising: a one-part moisture-curable polyurethane comprising a polycarbonate back bone and at least one end group derived from an aliphatic isocyanate; and a liquid hydrocarbon resin, wherein the liquid hydrocarbon resin is non-reactive with the at least one end group derived from an aliphatic isocyanate; and (b) curing the coating composition.
  • layer refers to any material or combination of materials on or overlaying a substrate.
  • (co)polymer or “(co)polymeric” includes homopolymers and copolymers, as well as homopolymers or copolymers that may be formed in a miscible blend, e.g., by coextrusion or by reaction, including, e.g., transesterification.
  • copolymer includes random, block, graft, and star copolymers.
  • nonpermeable as used herein means a film having a permeability of less than 1 perms according to ASTM E 96.
  • an aliphatic composition may comprise an aliphatic compound and/or a cycloaliphatic compound.
  • aliphatic compounds may also contain an aromatic ring provided that reactive groups in the compound are attached to an aliphatic portion of the compound and not to the aromatic portion of the compound, such as for example m-tetramethylxylene diisocyanate (meta-TMXDI).
  • reactive groups in the compound such as for example m-tetramethylxylene diisocyanate (meta-TMXDI).
  • diisocyanate refers to a compound containing two isocyanate groups.
  • polyisocyanate refers to a compound containing two or more isocyanate groups. Hence, diisocyanates are a subset of polyisocyanates.
  • an article having a continuous coating over a surface of a substrate may be a building envelope where the coating covers the entire outer surface of the building with no interruptions.
  • liquid as used herein means substances that have a definite volume but no fixed shape at ambient conditions.
  • Exemplary liquids useful in the present disclosure include solutions, mixtures, emulsions and suspensions where the primary component in such solutions, mixtures, emulsions and/or suspensions have a definite volume but no fixed shape at ambient conditions.
  • the present disclosure provides one component, moisture cure polyurethane coating
  • compositions that are useful in air barrier systems.
  • the presently disclosed coating compositions can be applied by spray, liquid, roller, trowel, as an article and/or a film and are non-permeable to air, water and water vapor.
  • the presently disclosed coating composition is liquid at ambient conditions.
  • the presently disclosed coating compositions include a one -part moisture-curable polyurethane comprising a polycarbonate back bone and at least one end group derived from an aliphatic isocyanate.
  • the polycarbonate back bone has a number average molecular weight of greater than 250 g/mol, more preferably greater than 300 g/mol and most preferably greater than 500 g/mol.
  • the one-part moisture-curable polyurethane includes a polyisocyanate.
  • Polyisocyanate means any organic compound that has two or more reactive isocyanate (— NCO) groups in a single molecule such as diisocyanates, triisocyanates, tetraisocyanates, etc., and mixtures thereof.
  • Polyisocyanate also includes oligomeric or polymeric isocyanates. Cyclic and/or linear polyisocyanate molecules may usefully be employed. For improved weathering and diminished yellowing, the polyisocyanate(s) of the isocyanate component is typically aliphatic. Useful aliphatic polyisocyanates include, for example, bis(4-isocyanatocyclohexyl) methane such as available from Bayer Corp., Pittsburgh, Pa.
  • the polyisocyanates include derivatives of the above-listed monomeric polyisocyanates. These derivatives include, but are not limited to, polyisocyanates containing biuret groups, such as the biuret adduct of hexamethylene diisocyanate (HDI) available from Bayer Corp. under the trade designation
  • DESMODUR N- 100 polyisocyanates containing isocyanurate groups, such as that available from Bayer Corp. under trade designation “DESMODUR N-3300” or “DESMODUR N-3900”, as well as polyisocyanates containing urethane groups, uretdione groups, carbodiimide groups, allophonate groups, and the like.
  • the one-part moisture-curable polyurethane includes a bis(oxazolidine)- based moisture-triggered isocyanate.
  • the one-part moisture-curable polyurethane includes a polycarbonate back bone and at least two end groups derived from an aliphatic isocyanate.
  • the aliphatic isocyanate in either of the end groups is derived from at least one of ethylene diisocyanate; 1,4- tetramethylene diisocyanate; 1 ,6-hexamethylene diisocyanate; 2,2,4-trimethyl- 1 ,6-hexamethylene diisocyanate; 1, 12-dodecamethylene diisocyanate; l-isocyanato-3-isocyanatomethyl-3,5,5-trimethyl- cyclohexane; bis-(4-isocyanatocyclohexyl)methane; bis-(4-isocyanato-3-methyl-cyclohexyl)methane; isophorone diisocyanate; dimer diisocyanate; m-tetramethylxylene diisocyanate.
  • the presently disclosed coating compositions also include a liquid hydrocarbon resin.
  • Hydrocarbon resin is useful to reduce moisture vapor transmittance rates for coating, articles and films made using the presently disclosed coating compositions.
  • Useful liquid hydrocarbon resins include liquid hydrocarbon resins that are non-reactive with the at least one end group derived from aliphatic isocyanate.
  • the liquid hydrocarbon resin comprises a polyisobutene, polybutene, polybutylene and materials as such.
  • the amount of hydrocarbon resin used in the coating composition is varied to achieve desired permeability of the coating composition and articles and films made therefrom.
  • the coating composition comprises IPDI (isophorone diisocyanate), polycarbonate prepolymer, urethane bisoxazolidine latent hardener, IPDI trimer and hydrocarbon resin.
  • the presently disclosed coating composition comprises at least 10 wt%, preferably 15 wt%, and most preferably 25 wt % of one-part moisture-curable polyurethane and hydrocarbon resin, based on the total weight of the coating composition.
  • Other ingredients useful in the presently disclosed coating compositions include antifoaming agents, wetting and dispersing agents, rheology modifiers, catalysts, pigments, extenders, solvents, fillers, light stabilizers and/or UV absorbers, dehydrators, and color additives.
  • the presently disclosed coating compositions may comprise one or more additives, such as, for example, "JONCRYL(R) 61 1" (BASF Corporation) and/or "NEOCRYL B734"
  • JONCRYL(R) 611 is a styrene-acrylic acid copolymer.
  • JONCRYL(R) 61 1 may be used as a dispersing agent in a moisture-curable coating composition to affect pigment dispersion and film-forming properties, for example.
  • NEOCRYL B-734 is a methyl methacrylate, n-butyl methacrylate copolymer resin.
  • NEOCRYL B734 may be used as a dispersing agent to affect pigment dispersion and film-forming properties, for example.
  • the presently disclosed coating compositions may comprise one or more pigments or fillers.
  • Useful fillers are typically solids that are non-reactive with the other components of the compositions of the invention.
  • Useful fillers include, for example, clay, talc, dye particles, pigments and colorants (for example, T1O2 or carbon black), glass beads, metal oxide particles, silica particles, ceramic microspheres, hollow polymeric microspheres (such as those available under the trade designation EXPANCEL 551 DE from Akzo Nobel, Duluth, Ga.), hollow glass microspheres (such as those available under the trade designation K37 from Minnesota Mining and Manufacturing Co., St Paul, Minn.), carbonates, metal oxides, silicates (e.g. talc, asbestos, clays, mica), sulfates, silicon dioxide and aluminum trihydrate.
  • ground or light calcium carbonate (with or without a surface- treatment such as a fatty acid, resin acid, cationic surfactant, or anionic surfactant); magnesium carbonate; talc; sulfates such as barium sulfate; alumina; metals in powder form (e.g., aluminum, zinc and iron); bentonite; kaolin clay; quartz powder; and combinations of two or more.
  • organic pigments examples include halogenated copper phthalocyanines, aniline blacks, anthraquinone blacks, benzimidazolones, azo condensations, arylamides, diarylides, disazo
  • condensations isoindolinones, isoindolines, quinophthalones, anthrapyrimidines, flavanthrones, pyrazolone oranges, perinone oranges, beta-naphthols, BON arylamides, quinacridones, perylenes, anthraquinones, dibromanthrones, pyranthrones, diketopyrrolo-pyrrole pigments (DPP), dioxazine violets, copper and copper- free phthalocyanines, indanthrones, and the like.
  • DPP diketopyrrolo-pyrrole pigments
  • useful inorganic pigments include titanium dioxide, zinc oxide, zinc sulphide, lithopone, antimony oxide, barium sulfate, carbon black, graphite, black iron oxide, black micaceous iron oxide, brown iron oxides, metal complex browns, lead chromate, cadmium yellow, yellow oxides, bismuth vanadate, lead chromate, lead molybdate, cadmium red, red iron oxide, Prussian blue, ultramarine, cobalt blue, chrome green (Brunswick green), chromium oxide, hydrated chromium oxide, organic metal complexes, laked dye pigments and the like.
  • the filler can also comprise conductive particles (see, for example, U.S. Patent Application Pub. No. 2003/0051807, which is incorporated herein by reference) such as carbon particles or metal particles of silver, copper, nickel, gold, tin, zinc, platinum, palladium, iron, tungsten, molybdenum, solder or the like, or particles prepared by covering the surface of these particles with a conductive coating of a metal or the like. It is also possible to use non-conductive particles of a polymer such as polyethylene, polystyrene, phenol resin, epoxy resin, acryl resin or benzoguanamine resin, or glass beads, silica, graphite or a ceramic, whose surfaces have been covered with a conductive coating of a metal or the like.
  • conductive particles see, for example, U.S. Patent Application Pub. No. 2003/0051807, which is incorporated herein by reference
  • non-conductive particles of a polymer such as polyethylene, polystyrene, phenol resin,
  • Preferred fillers include inorganic solids such, for example, talc, titanium dioxide, silica, zirconia, calcium carbonate, calcium magnesium carbonate, glass or ceramic microspheres, and combinations thereof. In some embodiments, titanium dioxide and/or calcium carbonate are preferred.
  • the coating composition of the present disclosure may comprise one or more pigment wetting agents or dispersants.
  • Pigment wetting agents and dispersants that may be useful in the present disclosure may include, for example, DISPERBYK(R)- 1 10 (BYK-Chemie GmbH),
  • the coating composition may comprise one or more rheology modifiers.
  • Rheology modifiers useful in the present disclosure may include, for example, BYK(R) 430, BYK(R) 431 (BYK-Chemie GmbH), Bentonite clays, and/or castor oil derivatives.
  • the presently disclosed coating composition may comprise one or more antifoaming agents.
  • Antifoaming agents useful in the present disclosure may include, for example, BYK(R) 077 (BYK-Chemie GmbH).
  • the presently disclosed coating compositions may comprise one or more light stabilizers and/or UV-absorbers.
  • Light stabilizers useful in the present disclosure may include, for example, TTNUVrN(R) 292 (Ciba/BASF).
  • UV-absorbers that may find utility in the presently disclosed coating composition may include, for example, TINUVIN(R) 1 130 (Ciba/BASF).
  • the coating composition may comprise one or more dehydrators.
  • Dehydrators useful in the presently disclosed coating composition may include, for example, p-toluenesulfonyl isocyanate, isophorone diisocyanate, and/or hexamethylene diisocyanate.
  • the presently disclosed coating composition may comprise one or more catalysts, such as, for example, dibutyltin dilaurate or a tertiary amine, to accelerate the curing reaction.
  • Catalysts that may find utility in the present disclosed coating composition may include, for example, DABCO(R) T-12 (Air Products and Chemicals, Inc.) and/or l,4-diazabicyclo[2.2.2]octane.
  • Other useful catalysts for the present disclosure include, but are not limited to, those catalysts that include both ether and morpholine functional groups, e.g., with 2,2-dimorpholinoethyl ether and di(2,6-dimethyl morpholinoethyl)ether.
  • a usefuil catalyst is 4,4'-(oxydi-2, l-ethanediyl) bis-morpholine, which known in the trade as DMDEE and is commercially available under the trade designation "JEFFCATE DMDEE” from Huntsman Corp. (Houston, Tex.).
  • catalysts include, e.g., organo tin catalysts, e.g., dibutyl tin dilaurate, and bismuth catalysts.
  • Bismuth octoate is a very good moisture cure catalyst, but is not as stable as some catalysts during shipping and storage where the temperatures may reach about 65 °C.
  • the catalyst is preferably present in the presently disclosed coating composition in an amount of from about 0.05% by weight about 5% by weight, more preferably from about 0.1% by weight to about 2% by weight, most preferably from about 0.1% by weight to about 1% by weight.
  • the coating composition may comprise one or more additional additives. Additional additives that may find utility in the presently disclosed coating composition may include, for example, Byk(R) 358, and/or Byk(R) 306 (BYK-Chemie GmbH).
  • the coating composition may comprise one or more solvents.
  • Solvent should be non-reactive with isocyanate and examples of such includes aliphatic, aromatic or araliphatic solvent which do not contain any cerivitinov-active hydrogen atoms but do preferably contain ether groups and/or ester groups and/or halogen atoms and/or nitrile groups and/or amide groups.
  • Suitable solvent include methoxypropyl acetate, methoxyethyl acetate, ethylene glycol diacetate, propylene glycol diacetate, glyme, diglyme, dioxane, tetrahydrofuran, dioxolane, tert-butyl methyl ether, ethyl acetate, butyl acetate, chloroform, methylene chloride, chlorobenzene, o-dichlorobenzene, anisole, 1,2-dimethoxybenzene, phenyl acetate, N-methyl-2-pyrrolidone, dimethylformamide, N,N- dimethylacetamide, dimethyl sulphoxide, acetonitrile, phenoxyethyl acetate and/or mixtures thereof, preferably solvent containing ether and ester groups, such as methoxypropyl acetate, acetone, 2-butanone, xylene, toluene, cyclohe
  • the presently disclosed coating composition is used to make an article having a substrate coated with a coating comprising the presently disclosed coating composition.
  • the coating is continuous.
  • thickness of the coating is varied to achieve desired permeability of the article.
  • the amount of hydrocarbon resin used in the coating composition is varied to achieve desired permeability of the article.
  • the amount of hydrocarbon resin used in the coating composition and the thickness of the coating are varied to achieve desired permeability of the article.
  • the present disclosure provides a film made using the presently disclosed coating composition.
  • the film has a permeability of less than 1 perms according to ASTM E 96.
  • the presently disclosed films have 300 % elongation and moisture vapor transmission rates of 0 perms to 1 perms according to ASTM E 96.
  • thickness of the coating is varied to achieve desired permeability of the film.
  • the amount of hydrocarbon resin used in the coating composition, which is used in the film is varied to achieve desired permeability of the film.
  • the amount of hydrocarbon resin used in the coating composition and the thickness of the coating are varied to achieve desired permeability of the film.
  • the presently disclosed coating composition is useful in a method of coating a substrate surface including the steps of applying the presently disclosed coating composition to a substrate surface and allowing it to cure.
  • the coating composition is applied at an ambient temperature of -20°C or higher.
  • the present disclosure also provides a method for preventing water vapor transport across a surface of a structure including the steps of: (a) coating at least a portion of the surface of the structure with any of the presently disclosed embodiments for a coating composition; and (b) curing the coating composition.
  • the coating composition, article and/or film is applied on an exterior sheathing layer, which is commonly plywood, oriented strand board (OSB), foam insulation sheathing, nonwoven glass mat faced gypsum sheathing board, or other conventional sheathing materials commonly used in the construction industry.
  • Useful exterior cladding layer is made up of brick, concrete blocks, reinforced concrete, stone, vinyl siding, fiber cement board, clapboard, or other known exterior siding materials.
  • the coating composition, article and/or film is applied to a roofing deck, an attic floor or other attic surface, a boundary between a wall, roof system, and/or foundation, other interior or exterior surfaces of a structure, or used as flashing around a roof penetration.
  • a coating composition comprising:
  • liquid hydrocarbon resin is non-reactive with the at least one end group derived from an aliphatic isocyanate.
  • composition of embodiment 1 wherein the coating composition is a liquid at ambient conditions.
  • the coating composition comprises at least 10 wt% of components (a) and (b) based on the total weight of the coating composition.
  • the liquid hydrocarbon resin comprises a polyisobutene.
  • composition of any of the preceding embodiments further comprising fillers.
  • composition of any of the preceding embodiments wherein the one -part moisture-curable polyurethane further comprises a second end group derived from an aliphatic isocyanate.
  • the aliphatic isocyanate is derived from ethylene diisocyanate; 1 ,4-tetramethylene diisocyanate; 1 ,6-hexamethylene diisocyanate; 2,2,4-trimethyl- 1 ,6- hexamethylene diisocyanate; 1, 12-dodecamethylene diisocyanate; l-isocyanato-3-isocyanatomethyl- 3,5,5-trimethyl-cyclohexane; bis-(4-isocyanatocyclohexyl)methane; bis-(4-isocyanato-3-methyl- cyclohexyl)methane; isophorone diisocyanate; dimer diisocyanate; m-tetramethylxylene diisocyanate; and
  • composition of any of the preceding embodiments wherein the polycarbonate back bone has a number average molecular weight of at least 500 g/mol.
  • An article comprising a substrate coated with a coating comprising the coating composition of any of the preceding embodiments. 13. The article of embodiment 12 wherein the coating is continuous.
  • a film comprising the coating composition of any of the preceding embodiments.
  • a method for preventing water vapor transport across a surface of a structure comprising:
  • a one-part moisture-curable polyurethane comprising a polycarbonate back bone and at least one end group derived from an aliphatic isocyanate
  • liquid hydrocarbon resin is non-reactive with the at least one end group derived from an aliphatic isocyanate
  • GLISSOPAL 1000 Low molecular weight polyisobutene, obtained from BASF,
  • PTSI para-toluene sulfonyl isocyanate obtained from Sigma-Aldrich
  • CAB-O-SIL TS-720 Medium surface area fumed silica which has been surface modified with polydimethylsiloxane, obtained from Cabot Corp., Bilieriea, MA
  • Moisture vapor transmittance rate (MVTR) of the example samples described below were determined in accordance with the ASTM E96 (2010) “Standard test method for water vapor transmission of materials", obtained from IHS Inc., Englewood, CO
  • EX1-EX3 samples were prepared form moisture cure polyurethane coating compositions made by mixing resins, pigments, specialty additives and solvents.
  • Table 1 summarizes the formulations for each of EX1-EX3 coating compositions.
  • To prepare each coating composition the desired ingredients were charged into a mixing vessel. The vessel was placed in a mixer (dual asymmetric centrifuge mixer, obtained under the trade designation "150 DAC SpeedMixer” from Flacktek, Inc Landrum, SC) and the contents were mixed at 2500 rounds per minute (rpm) for 4 minutes.
  • the resulting slurries were then applied on a TEFLON substrate by using a drawdown coater (Multiple Clearance Applicator PA-357 with a 40 mil (1.02 mm) clearance gap, obtained from BYK Gardner GmbH, Geretsried, MD) to form a coating with about a 40 mil (1.02 mm) wet thickness.
  • the coatings were allowed to cure at 20°C for 7 days. After curing the cured films were separated from the TEFLON substrate and the recovered cured film samples were tested.
  • MVTR of the cured EX1-EX3 samples were determined and summarized in Table 2, below.
  • the tensile and elongation testing of the cured EX1-EX3 samples were determined and summarized in Table 3, below.

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109321053A (zh) * 2018-09-14 2019-02-12 清远永昌涂料有限公司 一种基于热塑性丙烯酸树脂的刮涂型中涂汽车涂料及其制备方法
US10704254B2 (en) 2014-02-18 2020-07-07 3M Innovative Properties Company Easy to apply air and water barrier articles
US11731394B2 (en) 2014-12-22 2023-08-22 3M Innovative Properties Company Air and water barrier articles
US12403671B2 (en) 2015-12-22 2025-09-02 3M Innovative Properties Company Roll including air and water barrier article and method of using the same

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US20030051807A1 (en) 2000-03-24 2003-03-20 Hiroaki Yamaguchi Anisotropically conductive adhesive composition and anisotropically conductive adhesive film formed from it

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DE3200430A1 (de) * 1982-01-09 1983-07-21 Bayer Ag Verwendung von ein- oder mehrkomponentensystemen als bzw. zur herstellung von verbundmassen fuer glaskonstruktionen
US20130284364A1 (en) * 2010-10-25 2013-10-31 Marysusan Couturier Adhesives For Construction Materials Such As Tiles

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20030051807A1 (en) 2000-03-24 2003-03-20 Hiroaki Yamaguchi Anisotropically conductive adhesive composition and anisotropically conductive adhesive film formed from it

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10704254B2 (en) 2014-02-18 2020-07-07 3M Innovative Properties Company Easy to apply air and water barrier articles
US11731394B2 (en) 2014-12-22 2023-08-22 3M Innovative Properties Company Air and water barrier articles
US12403671B2 (en) 2015-12-22 2025-09-02 3M Innovative Properties Company Roll including air and water barrier article and method of using the same
CN109321053A (zh) * 2018-09-14 2019-02-12 清远永昌涂料有限公司 一种基于热塑性丙烯酸树脂的刮涂型中涂汽车涂料及其制备方法
CN109321053B (zh) * 2018-09-14 2021-03-23 清远永昌涂料有限公司 一种基于热塑性丙烯酸树脂的刮涂型中涂汽车涂料及其制备方法

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