US20170204289A1 - Hydroxy functional alkyl polyurea - Google Patents

Hydroxy functional alkyl polyurea Download PDF

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Publication number
US20170204289A1
US20170204289A1 US14/996,838 US201614996838A US2017204289A1 US 20170204289 A1 US20170204289 A1 US 20170204289A1 US 201614996838 A US201614996838 A US 201614996838A US 2017204289 A1 US2017204289 A1 US 2017204289A1
Authority
US
United States
Prior art keywords
coating
alkyl
hydroxy functional
amine
functional alkyl
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.)
Abandoned
Application number
US14/996,838
Other languages
English (en)
Inventor
Christopher P. Kurtz
John M. Dudik
Shanti Swarup
Edward R. Millero, Jr.
Hongying Zhou
Daniel Connor
Xiangling Xu
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
PPG Industries Ohio Inc
Original Assignee
PPG Industries Ohio Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by PPG Industries Ohio Inc filed Critical PPG Industries Ohio Inc
Priority to US14/996,838 priority Critical patent/US20170204289A1/en
Assigned to PPG INDUSTRIES OHIO, INC. reassignment PPG INDUSTRIES OHIO, INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: CONNOR, DANIEL, DUDIK, JOHN M, KURTZ, CHRISTOPHER P, MILLERO, EDWARD R, JR, SWARUP, SHANTI, XU, XIANGLING, ZHOU, HONGYING
Priority to CN202310046553.XA priority patent/CN115926511A/zh
Priority to AU2017207419A priority patent/AU2017207419B2/en
Priority to PCT/IB2017/050188 priority patent/WO2017122169A1/en
Priority to US16/069,580 priority patent/US10858535B2/en
Priority to US16/069,736 priority patent/US11203701B2/en
Priority to US16/069,561 priority patent/US10738215B2/en
Priority to KR1020187023269A priority patent/KR102258413B1/ko
Priority to EP17700092.4A priority patent/EP3402849B1/en
Priority to RU2018129474A priority patent/RU2737890C2/ru
Priority to PCT/US2017/013340 priority patent/WO2017123873A1/en
Priority to CA3011232A priority patent/CA3011232A1/en
Priority to KR1020187023268A priority patent/KR20180103978A/ko
Priority to PCT/IB2017/050189 priority patent/WO2017122170A1/en
Priority to RU2018129521A priority patent/RU2706629C1/ru
Priority to CN202211464279.XA priority patent/CN115851042A/zh
Priority to EP17702947.7A priority patent/EP3402853A1/en
Priority to CA3011362A priority patent/CA3011362A1/en
Priority to MX2018008547A priority patent/MX2018008547A/es
Priority to CN201780006634.XA priority patent/CN108463516B/zh
Priority to EP17704343.7A priority patent/EP3402833A1/en
Priority to KR1020187023271A priority patent/KR102170011B1/ko
Priority to KR1020187023266A priority patent/KR102188399B1/ko
Priority to PCT/US2017/013454 priority patent/WO2017123955A1/en
Priority to EP17704345.2A priority patent/EP3402848A1/en
Priority to KR1020217000080A priority patent/KR102432704B1/ko
Priority to AU2017206969A priority patent/AU2017206969A1/en
Priority to CN202110911842.2A priority patent/CN113831823A/zh
Priority to EP17702946.9A priority patent/EP3402850A1/en
Priority to CA3011325A priority patent/CA3011325A1/en
Priority to CN201780006633.5A priority patent/CN108463520A/zh
Priority to EP20206266.7A priority patent/EP3822322A1/en
Priority to KR1020187023276A priority patent/KR20180102635A/ko
Priority to RU2018129517A priority patent/RU2710431C1/ru
Priority to US16/069,662 priority patent/US10738216B2/en
Priority to PCT/EP2017/050724 priority patent/WO2017121879A1/en
Priority to ES17738272T priority patent/ES2935010T3/es
Priority to RU2018129499A priority patent/RU2733716C2/ru
Priority to AU2017207935A priority patent/AU2017207935B2/en
Priority to CN201780006573.7A priority patent/CN108473795A/zh
Priority to CA3011278A priority patent/CA3011278A1/en
Priority to MX2018008548A priority patent/MX2018008548A/es
Priority to CN201780006465.XA priority patent/CN108473645B/zh
Priority to MX2018008550A priority patent/MX2018008550A/es
Priority to CN201780006463.0A priority patent/CN108473794A/zh
Priority to EP17738272.8A priority patent/EP3402832B1/en
Priority to US16/069,785 priority patent/US10723913B2/en
Priority to MX2018008553A priority patent/MX2018008553A/es
Priority to MX2018008552A priority patent/MX2018008552A/es
Priority to US16/069,587 priority patent/US10858536B2/en
Priority to KR1020187023299A priority patent/KR102182370B1/ko
Priority to MX2018008500A priority patent/MX2018008500A/es
Priority to KR1020227027589A priority patent/KR20220116358A/ko
Priority to AU2017208147A priority patent/AU2017208147B2/en
Priority to PCT/IB2017/050191 priority patent/WO2017122171A2/en
Priority to CN201780006468.3A priority patent/CN108699202A/zh
Priority to TW106101461A priority patent/TW201741284A/zh
Priority to TW106101460A priority patent/TW201734087A/zh
Publication of US20170204289A1 publication Critical patent/US20170204289A1/en
Priority to MX2023004360A priority patent/MX2023004360A/es
Priority to US17/086,973 priority patent/US11286401B2/en
Priority to US17/529,409 priority patent/US20220073783A1/en
Abandoned legal-status Critical Current

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    • 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
    • C09D175/12—Polyurethanes from compounds containing nitrogen and active hydrogen, the nitrogen atom not being part of an isocyanate group
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/04—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms
    • C07C275/06—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton
    • C07C275/14—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton being further substituted by nitrogen atoms not being part of nitro or nitroso groups
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    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D7/00—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials
    • B05D7/14—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials to metal, e.g. car bodies
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
    • B27N—MANUFACTURE BY DRY PROCESSES OF ARTICLES, WITH OR WITHOUT ORGANIC BINDING AGENTS, MADE FROM PARTICLES OR FIBRES CONSISTING OF WOOD OR OTHER LIGNOCELLULOSIC OR LIKE ORGANIC MATERIAL
    • B27N3/00—Manufacture of substantially flat articles, e.g. boards, from particles or fibres
    • B27N3/002—Manufacture of substantially flat articles, e.g. boards, from particles or fibres characterised by the type of binder
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
    • B27N—MANUFACTURE BY DRY PROCESSES OF ARTICLES, WITH OR WITHOUT ORGANIC BINDING AGENTS, MADE FROM PARTICLES OR FIBRES CONSISTING OF WOOD OR OTHER LIGNOCELLULOSIC OR LIKE ORGANIC MATERIAL
    • B27N7/00—After-treatment, e.g. reducing swelling or shrinkage, surfacing; Protecting the edges of boards against access of humidity
    • B27N7/005—Coating boards, e.g. with a finishing or decorating layer
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
    • B65D—CONTAINERS FOR STORAGE OR TRANSPORT OF ARTICLES OR MATERIALS, e.g. BAGS, BARRELS, BOTTLES, BOXES, CANS, CARTONS, CRATES, DRUMS, JARS, TANKS, HOPPERS, FORWARDING CONTAINERS; ACCESSORIES, CLOSURES, OR FITTINGS THEREFOR; PACKAGING ELEMENTS; PACKAGES
    • B65D1/00—Containers having bodies formed in one piece, e.g. by casting metallic material, by moulding plastics, by blowing vitreous material, by throwing ceramic material, by moulding pulped fibrous material, by deep-drawing operations performed on sheet material
    • B65D1/12—Cans, casks, barrels, or drums
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/26—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of rings other than six-membered aromatic rings
    • 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
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/22—Catalysts containing metal 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
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/22—Catalysts containing metal compounds
    • C08G18/24—Catalysts containing metal compounds of tin
    • C08G18/244—Catalysts containing metal compounds of tin tin salts of carboxylic acids
    • C08G18/246—Catalysts containing metal compounds of tin tin salts of carboxylic acids containing also tin-carbon bonds
    • 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
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    • 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
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
    • C08G18/3271—Hydroxyamines
    • 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
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
    • C08G18/3271—Hydroxyamines
    • C08G18/3275—Hydroxyamines containing two hydroxy groups
    • 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
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/34—Carboxylic acids; Esters thereof with monohydroxyl compounds
    • C08G18/348—Hydroxycarboxylic acids
    • 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
    • C08G18/48—Polyethers
    • 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
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    • C08G18/48—Polyethers
    • C08G18/4854—Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • 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
    • C08G18/6692—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/34
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • C08G18/671—Unsaturated compounds having only one group containing active hydrogen
    • C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/73—Polyisocyanates or polyisothiocyanates acyclic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • C08G18/72—Polyisocyanates or polyisothiocyanates
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    • C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
    • C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
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    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • C08G18/755—Polyisocyanates 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • C08G18/78—Nitrogen
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    • 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
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • C08G18/80—Masked polyisocyanates
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    • C08G18/8041—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32 with compounds of C08G18/3271
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    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
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    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0016—Plasticisers
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    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/21—Urea; Derivatives thereof, e.g. biuret
    • 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
    • C08L75/04—Polyurethanes
    • C08L75/14—Polyurethanes having carbon-to-carbon unsaturated bonds
    • 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
    • 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
    • C09D175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
    • C09D175/16—Polyurethanes having carbon-to-carbon unsaturated bonds having terminal carbon-to-carbon unsaturated bonds
    • 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
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/02—Emulsion paints including aerosols
    • 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
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/03—Powdery paints
    • 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
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/60—Additives non-macromolecular
    • C09D7/63—Additives non-macromolecular organic

Definitions

  • the present invention is directed to hydroxy functional alkyl polyureas. Coatings comprising such polyureas are also within the scope of the present invention, as are substrates coated at least in part with such a coating.
  • Coatings are applied to numerous substrates to provide protective and/or decorative qualities. These coatings are often thermoset coatings, which cure upon reaction of a functional resin with a crosslinking agent having functionality that reacts with the functionality of the resin. Crosslinkers are often formaldehyde based. Many industries are interested in reducing if not eliminating formaldehyde in coatings. Coatings that are substantially, essentially or completely free of formaldehyde are desired. It is also desired by many industries to lower the temperature at which coatings cure.
  • the present invention is directed to a hydroxy functional alkyl polyurea having the formula:
  • R comprises the residue of an isocyanurate, biuret, allophonate, glycoluril, benzoguanamine, and/or polyetheramine; wherein each R1 is independently a hydrogen, alkyl having at least 1 carbon, or a hydroxy functional alkyl having 2 or more carbons and at least one R1 is a hydroxy functional alkyl having 2 or more carbons; and n is 2-6.
  • the present invention is also directed to a composition
  • a composition comprising a film forming resin; and a hydroxy functional alkyl polyurea crosslinker having the formula:
  • R2 is a substituted or unsubstituted C1 to C36 alkyl group, an aromatic group, the residue of an isocyanurate, biuret, allophanate, glycoluril, benzoguanamine and/or polyetheramine; wherein each R1 is independently a hydrogen, an alkyl having at least 1 carbon, or a hydroxy functional alkyl having 2 or more carbons; and n is 2-6.
  • the present invention is also directed to a hydroxy functional alkyl polyurea having the formula
  • R1 is as described above and R10 comprises the reaction product of isocyanate and an alkanol amine, but the isocyanate is not HDI when the alkanol amine is diethanol amine or monomethanol amine and the isocyanate is not IPDI when the alkanol amine is monomethanol amine.
  • the present invention is directed to hydroxy functional alkyl polyurea compounds as described below.
  • Such compounds can be used in various compositions including coatings, adhesives, and sealants, and can function, for example, as crosslinkers in such compositions.
  • the compounds may have the general formula:
  • R comprises the residue of an isocyanurate, biuret, allophonate, glycoluril, benzoguanamine, and/or polyetheramine; wherein each R1 is independently a hydrogen, an alkyl or a hydroxy functional alkyl having 2 or more carbons and at least one R1 is a hydroxy functional alkyl having 2 or more carbons; and n is 2-6.
  • the R1 group may exclude ether linkages.
  • hydroxy functional alkyl polyureas of the present invention can have the general formula
  • R1 is as described above and R10 comprises the reaction product of isocyanate and an alkanol amine, but the isocyanate is not HDI when the alkanol amine is diethanol amine or monomethanol amine and the isocyanate is not IPDI when the alkanol amine is monomethanol amine.
  • Suitable isocyanates can include hexamethylene diisocyanate (HDI), isophorone diisocyanate (IPDI), 4,4′-methylenedicyclohexyl diisocyanate (Des-W), tetramethylxylylene diisocyanate (TMXDI) and trimethyl hexamethylene diisocyanate (TMDI).
  • Suitable alkanol amines include diisopropanolamine (DIPA), diethanol amine (DEA), and monomethanol amine. Any combination of isocyanate and alkanol amine can be used other than those specifically excluded. Particularly suitable is the reaction product of HDI with DIPA, IPDI with DIPA and IPDI with DEA. The reaction between the isocyanate and alkanol amine can be done by any means known in the art, such as those reported in U.S. Pat. No. 3,420,787.
  • the present invention is further directed to a coating comprising:
  • R2 comprises a substituted or unsubstituted C1 to C36 alkyl group, an aromatic group, or the residue of an isocyanurate, biuret, allophonate, glycoluril, benzoguanamine, and/or polyetheramine; wherein each R1 is independently a hydrogen, an alkyl group having 1 or more carbons, or a hydroxy functional alkyl having 2 or more carbons and at least one R1 is a hydroxy functional alkyl having 2 or more carbons; and n is 2-6.
  • the R1 group may exclude ether linkages.
  • R and R2 may comprise the residue of an isocyanurate, biuret, allophonate, glycoluril, benzoguanamine and/or polyetheramine.
  • An isocyanurate will be understood as referring to a compound having three isocyanate groups, typically in ring form, and is sometimes referred to as a trimer. This can include compounds having one or more isocyanurate moieties. Isocyanurates can be purchased from COVESTRO and VENCORE X Chemical.
  • Suitable commercially available isocyanurates include DESMODUR N 3300A, DESMODUR N3800, DESMODUR N3400, DESMODUR N3600, DESMODUR N3900, DESMODUR RC, VESTANAT T1890/100, EASAQUA WT 2102, EASAQUA X D 401, EASAQUA M 501, EASAQUA X D 803, EASAQUA M 502, EASAQUA X L 600.
  • a particularly suitable hydroxy functional alkyl polyurea formed from an isocyanurate is shown below:
  • R1 is as described above and each R3 independently comprises an alkyl, aryl, alkylaryl, arylalkyl, alicyclic, and/or polyetheralkyl group.
  • a particularly suitable hydroxy functional alkyl polyurea formed from a bis-isocyanurate is shown below:
  • R1 and R3 are as described above.
  • a biuret will be understood as referring to a compound that results upon the condensation of two molecules of urea, and is sometimes referred to as a carbamylurea.
  • Biurets are commercial available from VENCORE X Chemical and COVESTRO as, for example, DESMODUR N-75, DESMODUR N-100, and DESMODUR N-3200, HDB 75B, HDB 75M, HDB 75MX, HDB-LV.
  • a particularly suitable hydroxy functional alkyl polyurea formed from a biuret is shown below:
  • each R5 independently comprises an alkyl, aryl, alkylaryl, arylalkyl, alicyclic, and/or polyetheralkyl group and R6 comprises H or an alkyl group.
  • Uretidione is a dimer of diisocyanate, examples of which include DESMODUR N-3400 polyisocyanate, a blend of the trimer and uretidione of HDI.
  • R 5 is as described above:
  • An allophonate will be understood as referring to a compound made from urethane and isocyanate.
  • a method for making an allophonate is described at Surface Coating, Vol 1, Raw material and their usage, Landon New York, Chapman and Hall, Page 106.
  • the reaction is generally depicted below where R 5 and R 6 are as described above and R 7 comprises the residue of a primary alcohol:
  • a glycoluril will be understood as referring to a compound composed of two cyclic urea groups joined across the same two-carbon chain, a suitable examples of which includes the below:
  • Glycoluril is widely commercially available, such as from Sigma-Aldrich.
  • Benzoguanamine is also known as 6-phenyl-1,3,5-triazine-2,4-diamine and is commercially available from The Chemical Company, Jamestown, R.I.
  • a polyether amine will be understood as referring to a compound having one or more amine groups attached to a polyether backbone such as one characterized by propylene oxide, ethylene oxide, or mixed propylene oxide and ethylene oxide repeating units in their respective structures, such as, for example, one of the Jeffamine series products.
  • polyetheramines include aminated propoxylated pentaerythritols, such as Jeffamine XTJ-616, and those represented by Formulas (IV) through (VI).
  • the polyether amine may comprise:
  • Suitable amine-containing compounds represented by Formula (IV) include, but are not limited to, amine-terminated polyethylene glycol such as those commercially available from Huntsman Corporation in its JEFFAMINE ED series, such as JEFFAMINE HK-511, JEFFAMINE ED-600, JEFFAMINE ED-900 and JEFFAMINE ED-2003, and amine-terminated polypropylene glycol such as in its JEFFAMINE D series, such as JEFFAMINE D-230, JEFFAMINE D-400, JEFFAMINE D-2000 and JEFFAMINE D-4000.
  • amine-terminated polyethylene glycol such as those commercially available from Huntsman Corporation in its JEFFAMINE ED series, such as JEFFAMINE HK-511, JEFFAMINE ED-600, JEFFAMINE ED-900 and JEFFAMINE ED-2003
  • amine-terminated polypropylene glycol such as in its JEFFAMINE D series
  • the polyetheramine may comprise:
  • each p independently is 2 or 3.
  • Suitable amine-containing compounds represented by Formula (V) include, but are not limited to, amine-terminated polyethylene glycol based diamines, such as Huntsman Corporation's JEFFAMINE EDR series, such as JEFFAMINE EDR-148 and JEFFAMINE EDR-176.
  • the polyetheramine may comprise:
  • Suitable amine-containing compounds represented by Formula (VI) include, but are not limited to, amine-terminated propoxylated trimethylolpropane or glycerol, such as Huntsman Corporation's JEFFAMINE T series, such as JEFFAMINE T-403, JEFFAMINE T-3000 and JEFFAMINE T-5000.
  • di- and tri-amines such as 4,7,10-trioxa-1,13-tridecanediamine, JEFFAMINE D400, JEFFAMINE D4000, JEFFAMINE D2000 and JEFFAMINE T403.
  • R, R2 and R10 may be substituted or unsubstituted.
  • R2, as noted above, may also comprise a substituted or unsubstituted C1 to C36 alkyl group and/or an aromatic group.
  • the alkyl group may have two to ten carbon atoms such as six carbon atoms.
  • the alkyl group may derive from an isocyanate, such as a diisocyanate. Suitable examples include isophorone diisocyanate and hexamethylene isocyanate.
  • the aromatic group may derive from an aromatic ring containing isocyanate, suitable examples of which include methylene diphenyl diisocyanate, toluene diisocyanate and tetramethylxylylene diisocyanate.
  • Certain hydroxy functional alkyl polyureas of, and/or used according to, the invention may be made by reacting an isocyanate-containing compound with amino alcohol. Any isocyanate-containing compound having at least two isocyanate groups can be used, such as any of those described above. It will be appreciated that the “R” “R2” or “R10” group will reflect the isocyanate-containing compound selected.
  • any amino alcohol having two or more carbon atoms can be used, and the “R1” group will reflect the amino alcohol selected.
  • the amino alcohol can have one, two or more hydroxyl functional groups.
  • One or more amino alcohols can be used, which will result in different R1 groups being present on the polyurea.
  • R1 can also be hydrogen or an alkyl group. Suitable amino alcohols include monoethanol amine, diethanol amine and diispropyl amine.
  • the hydroxyl functional alkyl polyureas can be made by reacting amino alcohol with an isocyanate-containing compound in an organic polar solvent, such as alcohol or water.
  • the reaction temperate can be kept below 35° C.
  • the equivalent ratio of amine to isocyanate can be 2-1:1-2, such as 1:1.
  • hydroxy functional alkyl polyureas of, and/or used according to, the invention may be made by alternative methods as well.
  • amino alcohols can react with carbonate to form hydroxylalkyl carbamate
  • hydroxylalkyl carbamate can further react with amines to form hydroxy functional alkyl polyureas.
  • the number average molecular weight (“Mn”) of the hydroxy functional alkyl polyurea can be 100 or greater, such as 350 or greater or 1000 or greater, and/or can be 6000 or lower, such as 3000 or lower, or 2000 or lower.
  • Mn means the theoretical value as determined by Gel Permeation Chromatography using Waters 2695 separation module with a Waters 410 differential refractometer (RI detector)) and polystyrene standards.
  • the range of molecular weights of the polystyrene standards for this method is from approximately 800 to 900,000 g/mol.
  • Tetrahydrofuran (THF) was used as the eluent at a flow rate of 1 ml min-1, and two PL Gel Mixed C columns were used for separation.
  • the present invention is further directed to a composition
  • a composition comprising a film forming resin and any of the hydroxy functional alkyl polyureas as described above.
  • the composition can be, for example, a coating, an adhesive or a sealant. It will be appreciated that coatings, sealants and adhesives often comprise similar components but are formulated differently depending on the needs of the user.
  • the hydroxy functional alkyl polyurea will typically react with the film forming resin to form the cured composition. For example, in a coating the polyurea will act as a crosslinking agent and react with the film forming resin to form a cured coating. Accordingly, the compositions of the present invention can achieve cure without formaldehyde-based crosslinking agents.
  • Formaldehyde-based crosslinking agents will be understood as those made by reacting amino compounds with formaldehyde followed by esterification with alkanols. Examples include, melamine formaldehyde crosslinkers like hexamethylol melamine and trimethylol melamine and aminoplast crosslinkers. When used as a crosslinker, the hydroxy functional alkyl polyurea may be used alone or in combination with one or more additional crosslinkers known in the art to crosslink, for example, with functionality on the film-forming resin.
  • crosslinker based on this functionality from known crosslinkers such as melamine, phenolic, carbodiimide, hydroxyalkylamide, isocyanate, blocked isocyanate, benzaguanamine, TGIC, epoxies, oxazolines, and the like.
  • any film forming resin that will react with the hydroxy functional alkyl polyurea can be used according to the present invention.
  • the film-forming resin can be selected from, for example, acrylic polymers, polyester polymers, polyurethane polymers, polyamide polymers, polyether polymers, polysiloxane polymers, copolymers thereof, and mixtures thereof.
  • these polymers can be any polymers of these types made by any method known to those skilled in the art.
  • Such polymers may be solvent-borne or water-dispersible, emulsifiable, or of limited water solubility.
  • the functional groups on the film-forming resin may be selected from any of a variety of reactive functional groups including, for example, carboxylic acid groups, amine groups, epoxide groups, hydroxyl groups, thiol groups, carbamate groups, amide groups, urea groups, isocyanate groups (including blocked isocyanate groups) mercaptan groups, and combinations thereof.
  • Appropriate mixtures of film-forming resins may also be used in the preparation of the present compositions, as can additional crosslinkers as noted above.
  • the composition can comprise, for example, 10 weight percent or greater of film forming resin, such as 50 weight percent or greater or 75 weight percent or greater and/or can comprise 99 weight percent or lower of film forming resin, such as 80 weight percent or lower or 70 weight percent or lower, with weight percent based on total solid weight of the coating.
  • the composition can comprise, for example, 0.5 weight percent or greater of hydroxy functional alkyl polyurea, such as 2 weight percent or greater or 7 weight percent or greater, and/or can comprise 30 weight percent or lower hydroxy functional alkyl polyurea, such as 20 weight percent or lower or 15 weight percent or lower, with weight percent based on total solid weight of the coating.
  • the composition may comprise one or more solvents including water or organic solvents.
  • Suitable organic solvents include glycols, glycol ether alcohols, alcohols, ketones, and aromatics, such as xylene and toluene, acetates, mineral spirits, naphthas and/or mixtures thereof.
  • “Acetates” include the glycol ether acetates.
  • the solvent can be a non-aqueous solvent.
  • “Non-aqueous solvent” and like terms means that less than 50% of the solvent is water. For example, less than 10%, or even less than 5% or 2%, of the solvent can be water. It will be understood that mixtures of solvents, including or excluding water in an amount of less than 50%, can constitute a “non-aqueous solvent”.
  • the composition may be aqueous or water-based. This means that 50% or more of the solvent is water. These embodiments have less than 50%, such as less than 20%, less than 10%, less than 5% or less than 2% solvent.
  • the composition may be in solid particulate form, i.e. a powder coating.
  • a powder coating Such coatings will be appreciated as being environmentally friendly, as only water is released on cure.
  • compositions of the present invention may further comprise a catalyst.
  • a catalyst Any catalyst typically used to catalyze crosslinking between a hydroxyl group and an acid may be used. Examples of such a catalyst include those having metal complexes with metals such as zinc, zirconium, titanium and tin and other Lewis acids. Amines, including guanamines, may also be used.
  • the use of a catalyst it will be appreciated, causes the cure of the coating to occur faster. Notably, catalysts are not effective at speeding the cure of beta-hydroxyl alkyl amides with the film forming resins listed above. Accordingly, it was a surprising result that catalysts promoted cure in the present coatings.
  • compositions can comprise other optional materials well known in the art of formulating, such as colorants, plasticizers, abrasion resistant particles, anti-oxidants, hindered amine light stabilizers, UV light absorbers and stabilizers, surfactants, flow control agents, thixotropic agents, fillers, organic cosolvents, reactive diluents, catalysts, grind vehicles, slip agents, moisture scavenger and other customary auxiliaries.
  • colorants such as colorants, plasticizers, abrasion resistant particles, anti-oxidants, hindered amine light stabilizers, UV light absorbers and stabilizers, surfactants, flow control agents, thixotropic agents, fillers, organic cosolvents, reactive diluents, catalysts, grind vehicles, slip agents, moisture scavenger and other customary auxiliaries.
  • colorant means any substance that imparts color and/or other opacity and/or other visual effect, e.g. gloss, to the composition.
  • the colorant can be added to the coating in any suitable form, such as discrete particles, dispersions, solutions and/or flakes.
  • a single colorant or a mixture of two or more colorants can be used in the coatings of the present invention.
  • Example colorants include matting pigments, dyes and tints, such as those used in the paint industry and/or listed in the Dry Color Manufacturers Association (DCMA), as well as special effect compositions.
  • a colorant may include, for example, a finely divided solid powder that is insoluble but wettable under the conditions of use.
  • a colorant can be organic or inorganic and can be agglomerated or non-agglomerated.
  • Colorants can be incorporated into the coatings by grinding or simple mixing. Colorants can be incorporated by grinding into the coating by use of a grind vehicle, such as an acrylic grind vehicle, the use of which will be familiar to one skilled in the art.
  • Example pigments and/or pigment compositions include, but are not limited to, carbazole dioxazine crude pigment, azo, monoazo, disazo, naphthol AS, salt type (lakes), benzimidazolone, condensation, metal complex, isoindolinone, isoindoline and polycyclic phthalocyanine, quinacridone, perylene, perinone, diketopyrrolo pyrrole, thioindigo, anthraquinone, indanthrone, anthrapyrimidine, flavanthrone, pyranthrone, anthanthrone, dioxazine, triarylcarbonium, quinophthalone pigments, diketo pyrrolo pyrrole red (“DPPBO red”), titanium dioxide, carbon black, carbon fiber, graphite, other conductive pigments and/or fillers and mixtures thereof.
  • the terms “pigment” and “colored filler” can be used interchangeably.
  • Example dyes include, but are not limited to, those that are solvent and/or aqueous based such as acid dyes, azoic dyes, basic dyes, direct dyes, disperse dyes, reactive dyes, solvent dyes, sulfur dyes, mordant dyes, for example, bismuth vanadate, anthraquinone, perylene aluminum, quinacridone, thiazole, thiazine, azo, indigoid, nitro, nitroso, oxazine, phthalocyanine, quinoline, stilbene, and triphenyl methane.
  • solvent and/or aqueous based such as acid dyes, azoic dyes, basic dyes, direct dyes, disperse dyes, reactive dyes, solvent dyes, sulfur dyes, mordant dyes, for example, bismuth vanadate, anthraquinone, perylene aluminum, quinacridone, thiazole, thiazine, azo, indigo
  • Example tints include, but are not limited to, pigments dispersed in water-based or water-miscible carriers such as AQUA-CHEM 896 commercially available from Degussa, Inc., CHARISMA COLORANTS and MAXITONER INDUSTRIAL COLORANTS commercially available from Accurate Dispersions division of Eastman Chemicals, Inc.
  • AQUA-CHEM 896 commercially available from Degussa, Inc.
  • CHARISMA COLORANTS and MAXITONER INDUSTRIAL COLORANTS commercially available from Accurate Dispersions division of Eastman Chemicals, Inc.
  • the colorant can be in the form of a dispersion including, but not limited to, a nanoparticle dispersion.
  • Nanoparticle dispersions can include one or more highly dispersed nanoparticle colorants and/or colorant particles that produce a desired visible color and/or opacity and/or visual effect.
  • Nanoparticle dispersions can include colorants such as pigments or dyes having a particle size of less than 150 nm, such as less than 70 nm, or less than 30 nm. Nanoparticles can be produced by milling stock organic or inorganic pigments with grinding media having a particle size of less than 0.5 mm. Example nanoparticle dispersions and methods for making them are identified in U.S. Pat. No.
  • Nanoparticle dispersions can also be produced by crystallization, precipitation, gas phase condensation, and chemical attrition (i.e., partial dissolution).
  • a dispersion of resin-coated nanoparticles can be used.
  • a “dispersion of resin-coated nanoparticles” refers to a continuous phase in which is dispersed discreet “composite microparticles” that comprise a nanoparticle and a resin coating on the nanoparticle.
  • Example dispersions of resin-coated nanoparticles and methods for making them are described, for example, in U.S. Pat. No. 7,605,194 at column 3, line 56 to column 16, line 25, the cited portion of which being incorporated herein by reference.
  • Example special effect compositions that may be used include pigments and/or compositions that produce one or more appearance effects such as reflectance, pearlescence, metallic sheen, phosphorescence, fluorescence, photochromism, photosensitivity, thermochromism, goniochromism and/or color-change. Additional special effect compositions can provide other perceptible properties, such as opacity or texture. For example, special effect compositions can produce a color shift, such that the color of the coating changes when the coating is viewed at different angles. Example color effect compositions are identified in U.S. Pat. No. 6,894,086, incorporated herein by reference.
  • Additional color effect compositions can include transparent coated mica and/or synthetic mica, coated silica, coated alumina, a transparent liquid crystal pigment, a liquid crystal coating, and/or any composition wherein interference results from a refractive index differential within the material and not because of the refractive index differential between the surface of the material and the air.
  • a photosensitive composition and/or photochromic composition which reversibly alters its color when exposed to one or more light sources, can be used in the coating of the present invention.
  • Photochromic and/or photosensitive compositions can be activated by exposure to radiation of a specified wavelength. When the composition becomes excited, the molecular structure is changed and the altered structure exhibits a new color that is different from the original color of the composition. When the exposure to radiation is removed, the photochromic and/or photosensitive composition can return to a state of rest, in which the original color of the composition returns.
  • the photochromic and/or photosensitive composition can be colorless in a non-excited state and exhibit a color in an excited state. Full color-change can appear within milliseconds to several minutes, such as from 20 seconds to 60 seconds.
  • Example photochromic and/or photosensitive compositions include photochromic dyes.
  • the photosensitive composition and/or photochromic composition can be associated with and/or at least partially bound to, such as by covalent bonding, a polymer and/or polymeric materials of a polymerizable component.
  • the photosensitive composition and/or photochromic composition associated with and/or at least partially bound to a polymer and/or polymerizable component in accordance with the present invention have minimal migration out of the coating.
  • Example photosensitive compositions and/or photochromic compositions and methods for making them are identified in U.S. Pat. No. 8,153,344, and incorporated herein by reference.
  • the colorant can be present in any amount sufficient to impart the desired visual and/or color effect.
  • the colorant may comprise from 1 to 65 weight percent of the present compositions, such as from 3 to 40 weight percent or 5 to 35 weight percent, with weight percent based on the total weight of the compositions.
  • abrasion resistant particle is one that, when used in a coating, will impart some level of abrasion resistance to the coating as compared with the same coating lacking the particles.
  • Suitable abrasion resistant particles include organic and/or inorganic particles. Examples of suitable organic particles include but are not limited to diamond particles, such as diamond dust particles, and particles formed from carbide materials; examples of carbide particles include but are not limited to titanium carbide, silicon carbide and boron carbide.
  • suitable inorganic particles include but are not limited to silica; alumina; alumina silicate; silica alumina; alkali aluminosilicate; borosilicate glass; nitrides including boron nitride and silicon nitride; oxides including titanium dioxide and zinc oxide; quartz; nepheline syenite; zircon such as in the form of zirconium oxide; buddeluyite; and eudialyte. Particles of any size can be used, as can mixtures of different particles and/or different sized particles.
  • the particles can be microparticles, having an average particle size of 0.1 to 50, 0.1 to 20, 1 to 12, 1 to 10, or 3 to 6 microns, or any combination within any of these ranges.
  • the particles can be nanoparticles, having an average particle size of less than 0.1 micron, such as 0.8 to 500, 10 to 100, or 100 to 500 nanometers, or any combination within these ranges.
  • slip agent can be used according to the present invention such as those commercial available from BYK Chemie or Dow Corning.
  • a wax can also be used such as polyolefin wax, silicone or paraffin.
  • the hydroxy functional alkyl polyureas, and/or the compositions of the present invention may be substantially free, may be essentially free and/or may be completely free of bisphenol A and epoxy compounds derived from bisphenol A (“BPA”), such as bisphenol A diglycidyl ether (“BADGE”).
  • BPA bisphenol A
  • BADGE bisphenol A diglycidyl ether
  • BPA non intent because BPA, including derivatives or residues thereof, are not intentionally added but may be present in trace amounts because of impurities or unavoidable contamination from the environment.
  • the hydroxy functional alkyl polyureas and/or coatings can also be substantially free and may be essentially free and/or may be completely free of bisphenol F and epoxy compounds derivatived from bisphenol F, such as bisphenol F diglycidyl ether (“BFDGE”).
  • substantially free means the and/or coatings contain less than 1000 parts per million (ppm), “essentially free” means less than 100 ppm and “completely free” means less than 20 parts per billion (ppb) of any of the above mentioned compounds, derivatives or residues thereof.
  • hydroxy functional alkyl polyureas and/or the composition of the present invention may be substantially free, may be essentially free and/or may be completely free of formaldehyde.
  • substantially free as used in this context means the and/or coatings contain less than 1000 parts per million (ppm), “essentially free” means less than 100 ppm and “completely free” means less than 100 parts per billion (ppb) of formaldehyde compounds, derivatives or residues thereof.
  • compositions can be applied to any substrates known in the art, for example, automotive substrates, marine substrates, industrial substrates, packaging substrates, wood flooring and furniture, apparel, electronics including housings and circuit boards and including consumer electronics such as housings for computers, notebooks, smartphones, tablets, televisions, gaming equipment, computer equipment, computer accessories, MP3 players, and the like, glass and transparencies, sports equipment including golf balls, and the like.
  • substrates can be, for example, metallic or non-metallic.
  • Metallic substrates include tin, steel, tin-plated steel, chromium passivated steel, galvanized steel, aluminum, aluminum foil.
  • Metal sheet as used herein refers to flat metal sheet and coiled metal sheet, which is coiled, uncoiled for coating and then re-coiled for shipment to a manufacturer.
  • Non-metallic substrates include polymeric, plastic, polyester, polyolefin, polyamide, cellulosic, polystyrene, polyacrylic, poly(ethylene naphthalate), polypropylene, polyethylene, nylon, EVOH, polylactic acid, other “green” polymeric substrates, poly(ethyleneterephthalate) (“PET”), polycarbonate, polycarbonate acrylobutadiene styrene (“PC/ABS”), polyamide, wood, veneer, wood composite, particle board, medium density fiberboard, cement, stone, glass, paper, cardboard, textiles, leather both synthetic and natural, and the like.
  • the substrate can be one that has been already treated in some manner, such as to impart visual and/or color effect. Suitable substrates can include those in which powder coatings are typically applied.
  • compositions of the present invention can be applied by any means standard in the art, such as electrocoating, spraying, electrostatic spraying, dipping, rolling, brushing, and the like.
  • compositions can be applied to a dry film thickness of 0.04 mils to 4 mils, such as 0.3 to 2 or 0.7 to 1.3 mils.
  • the compositions can also be applied to a dry film thickness of 0.1 mils or greater, 0.5 mils or greater 1.0 mils or greater, 2.0 mils or greater, 5.0 mils or greater, or even thicker.
  • compositions of the present invention can be used alone, or in combination with one or more other compositions, such as a coating system having two or more layers.
  • the compositions of the present invention can comprise a colorant or not and can be used as a primer, basecoat, and/or top coat.
  • a primer for substrates coated with multiple coatings, one or more of those coatings can be coatings as described herein.
  • the present coatings can also be used as a packaging “size” coating, wash coat, spray coat, end coat, and the like.
  • compositions described herein can be either one component (“1K”), or multi-component compositions such as two component (“2K”) or more.
  • a 1K composition will be understood as referring to a composition wherein all the coating components are maintained in the same container after manufacture, during storage, etc.
  • a 1K composition can be applied to a substrate and cured by any conventional means, such as by heating, forced air, and the like.
  • the present compositions can also be multi-component, which will be understood as compositions in which various components are maintained separately until just prior to application.
  • the present compositions can be thermoplastic or thermosetting.
  • the composition can be a clearcoat.
  • a clearcoat will be understood as a coating that is substantially transparent or translucent. A clearcoat can therefore have some degree of color, provided it does not make the clearcoat opaque or otherwise affect, to any significant degree, the ability to see the underlying substrate.
  • the clearcoats of the present invention can be used, for example, in conjunction with a pigmented basecoat.
  • the clearcoat can be formulated as is known in the coatings art.
  • the composition may also comprise a colorant, such as a pigmented basecoat used in conjunction with a clearcoat, or as a pigmented monocoat.
  • a colorant such as a pigmented basecoat used in conjunction with a clearcoat, or as a pigmented monocoat.
  • Such coating layers are used in various industries to impart a decorative and/or protective finish.
  • a coating or coating system may be applied to a vehicle.
  • Vehicle is used herein in its broadest sense and includes all types of vehicles, such as but not limited to cars, trucks, buses, vans, golf carts, motorcycles, bicycles, railroad cars, airplanes, helicopters and the like. It will be appreciated that the portion of the vehicle that is coated according to the present invention may vary depending on why the coating is being used. For example, anti-chip primers may be applied to some of the portions of the vehicle as described above.
  • the present coatings When used as a colored basecoat or monocoat, the present coatings will typically be applied to those portions of the vehicle that are visible such as the roof, hood, doors trunk lid and the like, but may also be applied to other areas such as inside the trunk, inside the door and the like especially when the compositions are formulated as sealants or adhesives; they can also be applied to those portions of the car that are in contact with the driver and/or passengers, such as the steering wheel, dashboard, gear shift, controls, door handle and the like. Clearcoats will typically be applied to the exterior of a vehicle.
  • compositions of the present invention are also suitable for use as packaging coatings.
  • the application of various pretreatments and coatings to packaging is well established.
  • Such treatments and/or coatings can be used in the case of metal cans, wherein the treatment and/or coating is used to retard or inhibit corrosion, provide a decorative coating, provide ease of handling during the manufacturing process, and the like.
  • Coatings can be applied to the interior of such cans to prevent the contents from contacting the metal of the container. Contact between the metal and a food or beverage, for example, can lead to corrosion of a metal container, which can then contaminate the food or beverage. This is particularly true when the contents of the can are acidic in nature.
  • the coatings applied to the interior of metal cans also help prevent corrosion in the headspace of the cans, which is the area between the fill line of the product and the can lid; corrosion in the headspace is particularly problematic with food products having a high salt content.
  • Coatings can also be applied to the exterior of metal cans.
  • Certain coatings of the present invention are particularly applicable for use with coiled metal stock, such as the coiled metal stock from which the ends of cans are made (“can end stock”), and end caps and closures are made (“cap/closure stock”). Since coatings designed for use on can end stock and cap/closure stock are typically applied prior to the piece being cut and stamped out of the coiled metal stock, they are typically flexible and extensible. For example, such stock is typically coated on both sides.
  • the coated metal stock is punched.
  • the metal is then scored for the “pop-top” opening and the pop-top ring is then attached with a pin that is separately fabricated.
  • the end is then attached to the can body by an edge rolling process.
  • a similar procedure is done for “easy open” can ends.
  • a score substantially around the perimeter of the lid allows for easy opening or removing of the lid from the can, typically by means of a pull tab.
  • the cap/closure stock is typically coated, such as by roll coating, and the cap or closure stamped out of the stock; it is possible, however, to coat the cap/closure after formation. Coatings for cans subjected to relatively stringent temperature and/or pressure requirements should also be resistant to popping, corrosion, blushing and/or blistering.
  • the present invention is further directed to a package coated at least in part with any of the coating compositions described above.
  • a “package” is anything used to contain another item, particularly for shipping from a point of manufacture to a consumer, and for subsequent storage by a consumer.
  • a package will be therefore understood as something that is sealed so as to keep its contents free from deterioration until opened by a consumer.
  • the manufacturer will often identify the length of time during which the food or beverage will be free from spoilage, which typically ranges from several months to years.
  • the present “package” is distinguished from a storage container or bakeware in which a consumer might make and/or store food; such a container would only maintain the freshness or integrity of the food item for a relatively short period.
  • a package according to the present invention can be made of metal or non-metal, for example, plastic or laminate, and be in any form.
  • An example of a suitable package is a laminate tube.
  • Another example of a suitable package is metal can.
  • the term “metal can” includes any type of metal can, container or any type of receptacle or portion thereof that is sealed by the food/beverage manufacturer to minimize or eliminate spoilage of the contents until such package is opened by the consumer.
  • One example of a metal can is a food can; the term “food can(s)” is used herein to refer to cans, containers or any type of receptacle or portion thereof used to hold any type of food and/or beverage.
  • metal can(s) specifically includes food cans and also specifically includes “can ends” including “E-Z open ends”, which are typically stamped from can end stock and used in conjunction with the packaging of food and beverages.
  • the term “metal cans” also specifically includes metal caps and/or closures such as bottle caps, screw top caps and lids of any size, lug caps, and the like.
  • the metal cans can be used to hold other items as well, including, but not limited to, personal care products, bug spray, spray paint, and any other compound suitable for packaging in an aerosol can.
  • the cans can include “two piece cans” and “three-piece cans” as well as drawn and ironed one-piece cans; such one piece cans often find application with aerosol products.
  • Packages coated according to the present invention can also include plastic bottles, plastic tubes, laminates and flexible packaging, such as those made from PE, PP, PET and the like. Such packaging could hold, for example, food, toothpaste, personal care products and the like.
  • the coating can be applied to the interior and/or the exterior of the package.
  • the coating can be rollcoated onto metal used to make a two-piece food can, a three-piece food can, can end stock and/or cap/closure stock.
  • the coating is applied to a coil or sheet by roll coating; the coating is then cured by radiation and can ends are stamped out and fabricated into the finished product, i.e. can ends.
  • the coating could also be applied as a rim coat to the bottom of the can; such application can be by roll coating.
  • the rim coat functions to reduce friction for improved handling during the continued fabrication and/or processing of the can.
  • the coating can also be applied to caps and/or closures; such application can include, for example, a protective varnish that is applied before and/or after formation of the cap/closure and/or a pigmented enamel post applied to the cap, particularly those having a scored seam at the bottom of the cap.
  • Decorated can stock can also be partially coated externally with the coating described herein, and the decorated, coated can stock used to form various metal cans.
  • Coil coatings also typically comprise a colorant.
  • the coating composition may be cured by any appropriate means.
  • a cure of 140° C. or lower such as 130° C. or lower or 125° C. or lower for 30 minutes or less, such as y minutes or less may be desired and can be achieved according to the present invention.
  • a cure of 250° C. or lower such as 235° C. or lower or 200° C. or lower but for a time of three minutes or less, such as two minutes or less, or one minute or less, or 30 seconds or less or 15 seconds or less, may be desired and can be achieved according to the present invention.
  • the present coatings can be used across a broad range of industries and cure conditions.
  • HAU compounds as described herein can be used in thermoplastic acid functional polymers such polyesters, ethylene acrylic acid copolymers and terpolmers, and ionomers.
  • thermoplastic acid functional polymers such polyesters, ethylene acrylic acid copolymers and terpolmers, and ionomers.
  • HAU compounds can serve as cross-linkers, chain extenders, to increase the hydrolysis resistance of polyesters, and modify viscosity for applications such as extruded fibers, films, injection molded articles, extrusion coating, blow molding, extrusion blowmolding, and extrusion.
  • HAU can also be used in applications currently employing carbodiimide additives.
  • polymer refers to oligomers and both homopolymers and copolymers, and the prefix “poly” refers to two or more. Including, for example and like terms means including for example but not limited to. When ranges are given, any endpoints of those ranges and/or numbers within those ranges can be combined within the scope of the present invention.
  • Non-limiting aspects of the invention include:
  • a hydroxy functional alkyl polyurea having the formula:
  • R comprises the residue of an isocyanurate, biuret, allophonate, glycoluril, benzoguanamine, and/or polyetheramine; or R comprises the reaction product of an isocyanate and an alkanol amine but the isocyanate is not HDI when the alkanol amine is diethanol amine or monomethanol amine and the isocyanate is not IPDI when the alkanol amine is monomethanol amine; wherein each R1 is independently a hydrogen, alkyl having at least 1 carbon, or a hydroxy functional alkyl having 2 or more carbons and at least one R1 is a hydroxy functional alkyl having 2 or more carbons; and n is 2-6.
  • R comprises the residue of an isocyanurate.
  • at least one R1 comprises an ethanol or isopropanol group.
  • IPDI isophorone diisocyanate
  • Example 9A A OH terminated polyurethane was prepared by the following procedure. 100 g of 2-ethylhexyl acrylate (EHA), 79.2 g of hydroxyethyl methacrylate (HEMA), 1.5 g of 2,6-di-tert-butyl 4-methyl phenol, 0.78 g of triphenyl phosphite, 0.78 g of dibutyl tin dilaurate, 405 g of polytetrahydrofuran with number average molecular weight 1000, 81.6 g of dimethyol propionic acid, and 4 g of triethyl amine were charged in order into a four necked round bottom flask fitted with a thermocouple, mechanical stirrer, and condenser.
  • EHA 2-ethylhexyl acrylate
  • HEMA hydroxyethyl methacrylate
  • 2,6-di-tert-butyl 4-methyl phenol 0.78 g of trip
  • the mixture was heated to 90° C. and held for 15 minutes. After that, 405.5 g of isophorone diisocyanate was charged into the flask over 90 minutes. After that, the isocyanate adding funnel was rinsed with 20 g of 2-ethylhexyl acrylate. The mixture was held at 90° C. until all of the isocyanate IR peak was gone. After that, 454 g of 2-ethylhexyl acrylate and 72.5 DOWANOL PM were charged into flask, and cooled to ambient temperature. The acid value of the polyurethane was measure to be 23.5 mgKOH/g, and weight average molecular weight by GPC was 7269.
  • Example 9B A carboxyl functionalized polyurethane/acrylic latex was prepared as follows. 545 g of deionized water, 15.6 g of AEROSOL OT-75 from Cytec, 10.7 g of dimethyl ethanolamine, 298 g of the OH terminated polyurethane prepared according to Example 9A, 74.4 g of methyl methacrylate, and 11.1 g of hexanediol diacrylate was charged in order to a four necked round bottom flask fitted with a thermocouple, mechanical stirrer, and condenser. The mixture was heated to 33° C. and held for 30 minutes with a N 2 blanket.
  • the resulting latex had a solid content of 38.5%, and the volume average particle size measured by Zetasizer was 104 nm.
  • Different hydroxyl functional alkyl polyureas of the present invention were mixed with the acid functional polymer of Example 9B at a COOH/OH ratio of 1/1.
  • the mixture was drawn down to panel with a wet thickness of 100 micrometer.
  • the film was dried at room temperature for 15 minutes, and followed by baking at different temperatures for 30 minutes. After cooling at room temperature for 30 minutes, panels were tested for MEK double rubs.
  • TYZOR LA catalogalyst, available from Dorf Ketal Chemical, LLC. This solution was drawn down on a panel, followed by a 30 minutes bake at different temperature and tested for MEK double rubs.
  • Example 1 and acid functionalized PU/acrylate were mixed at a COOH/OH ratio of 1/1 and different catalyst as shown below (1% based on mixture) were mixed in.
  • the mixtures were then drawn down to panel with a wet thickness of 100 micrometer.
  • the film was dried at room temperature for 15 minutes, and followed by baking at different temperature for 30 minutes. After cooling at room temperature for 30 minutes, panels were tested for MEK double rubs.
  • TYZOR LA As shown in the following Table 2, TYZOR LA, TYZOR 131 (catalyst, available from Dorf Ketal Chemical, LLC), and DBTDL performed better than control without catalyst.
  • Example 1 and TYZOR LA (1% based on mixture) were mixed with acid functionalized PU/acrylate (example 9B) at a COOH/OH ratio of 1/1. The mixture was then drawn down to panel with a wet thickness of 100 micrometer. The film was dried at room temperature for 15 minutes, and followed by baking at different temperature for 30 minutes. After cooling at room temperature for 30 minutes, panels were tested with different solvent for double rubs.
  • Example 13 The coating of Example 13 was prepared by combining all of the materials shown in Table Y and mixing for 10 minutes with a mixing blade.
  • Coated panels were obtained by drawing the coating over chrome treated 5182-H48 aluminum panels using a wire wound rod to obtain dry coating weights of 2.0-2.5 mg/square inch (msi).
  • the coated panels were immediately placed into a one-zone, gas-fired, conveyor oven for 15 seconds and baked to a peak metal temperature of 400° F. (204° C.) or 320° F. (160° C.).
  • the baked panels were immediately tested for hot tack cure test.
  • the minimum cure temperature was determined for a film to achieve resistance to damage when rubbed at an elevated temperature and compared to a control.
  • the panel was immediately placed on a 60° C. hot plate.
  • the hot plate temperature is controlled to mimic the can temperature as measured at the “deco oven” exit on a commercial can line.
  • gauze 4′′ ⁇ 4′′-12 ply gauze pad
  • the panel was held against the hot plate for at least 5 seconds. Resting the gauze covered hammer head on the panel, the coated surface was double rubbed 5 times. The tack resistance was rated for mar resistance.
  • a second bake was subsequently applied to the panel to simulate an inside spray bake and to obtain the final properties of the overvarnish.
  • the baked panel from the gas conveyor oven was placed in a 204C box oven for 3 minutes.
  • the panels were cooled down and evaluated for MEK double rubs and Joy Detergent tests.
  • the MEK double rub test rub used a gauze covered hammer that was saturated with methyl ethyl ketone.
  • the coatings were evaluated for the number of double rubs it took to soften and break through the coating or until 50 double rubs were performed.
  • the coatings were also evaluated for their ability to adhere to the aluminum panels and to resist blushing in the Joy detergent test. The results of the test are reported in Table 2.
  • Blush resistance measured the ability of a coating to resist attack by various testing solutions. When the coated film absorbs test solution, it generally becomes cloudy or looks white. Blush was measured visually using a scale of 1-10 where a rating of “10” indicates no blush and a rating of “0” indicates complete whitening of the film. Blush ratings of at least 6 are typically desired for commercially viable coatings. The coated panel tested was 2 ⁇ 4 inches (5 ⁇ 10 cm) and the testing solution covered half of the panel being tested so you can compare blush of the exposed panel to the unexposed portion.
  • Adhesion testing was performed to assess whether the coating adheres to the substrate.
  • the adhesion test was performed according to ASTM D 3359 Test Method B, using Scotch 610 tape, available from 3M Company of Saint Paul, Minn.
  • Adhesion was generally rated on a scale of 1-10 where a rating of “10” indicates no adhesion failure, a rating of “9” indicated 90% of the coating remains adhered, a rating of “8” indicates 80% of the coating remained adhered, and so on.
  • the “Joy” test measured the resistance of a coating to a hot 82° C. Joy detergent solution.
  • the solution was prepared by mixing 30 grams of Ultra Joy Dishwashing Liquid (product of Procter & Gamble) into 3000 grams of deionized water. Coated strips were immersed into the 82° C. Joy solution for 15 minutes. The strips were then rinsed and cooled in deionized water, dried, and immediately rated for blush as described previously.
  • *PPG 3805803 is a commercial water reducible varnish from PPG Industries. It contains two water reducible acrylic resins and melamine (formaldehyde containing).
  • the hydroxyl functional alkyl polyureas of Example 1 and Example 3 were each mixed with an internally produced acrylic latex polymer that had a solid content of 29.8% when measured after heating a sample to 110° C. for 1 hour and a measured acid value of 12.8 mg KOH/g.
  • a suitable acrylic latex can be prepared, for example, according to the procedures outlined by Perez in U.S. Pat. No. 5,714,539.
  • the crosslinkers of Example 1 and Example 3 were added in various amounts to achieve different ratios of COOH/OH as indicated in Table 7.
  • To the mixtures were added 10% on solids of ethylene glycol mono-2-ethylhexyl ether (purchased from Eastman as Ektasolve EEH).
  • Ektasolve EEH ethylene glycol mono-2-ethylhexyl ether
  • the cured coatings were tested for solvent resistance using the “MEK Double Rub” test described in Example 13.
  • the cured coating was also evaluated with the Acetic Acid Test.
  • the Acetic Acid Test measured the resistance of the coating to a boiling 3% acetic acid solution.
  • the solution was prepared by mixing 90 g of glacial acetic acid (product of Fisher Scientific) into 3000 g of deionized water. Coated strips were immersed into the boiling acetic acid solution for 30 minutes. The strips were then rinsed and cooled in deionized water, dried, and immediately rated for blush. Blush was measured and reported in Example 13.
  • the cured coatings were checked for solvent resistance using the MEK double rub test. As shown in the following Table, the MEK Double Rubs results improve with the inclusion of the hydroxyl alkyl functional polyuria as compared to no HAU.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Materials Engineering (AREA)
  • Manufacturing & Machinery (AREA)
  • Forests & Forestry (AREA)
  • Ceramic Engineering (AREA)
  • Mechanical Engineering (AREA)
  • Dispersion Chemistry (AREA)
  • Paints Or Removers (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Laminated Bodies (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US14/996,838 2016-01-15 2016-01-15 Hydroxy functional alkyl polyurea Abandoned US20170204289A1 (en)

Priority Applications (61)

Application Number Priority Date Filing Date Title
US14/996,838 US20170204289A1 (en) 2016-01-15 2016-01-15 Hydroxy functional alkyl polyurea
CN202310046553.XA CN115926511A (zh) 2016-01-15 2017-01-13 具有涂料组合物的单块气溶胶管或罐
AU2017207419A AU2017207419B2 (en) 2016-01-15 2017-01-13 Hydroxy functional alkyl polyurea containing compositions
PCT/IB2017/050188 WO2017122169A1 (en) 2016-01-15 2017-01-13 A coating composition comprising a thermoset resin and a thermoplastic resin
US16/069,580 US10858535B2 (en) 2016-01-15 2017-01-13 Coating composition comprising a powder dispersed in a liquid carrier
US16/069,736 US11203701B2 (en) 2016-01-15 2017-01-13 Hydroxy functional alkyl polyurea crosslinkers
US16/069,561 US10738215B2 (en) 2016-01-15 2017-01-13 Monobloc aerosol tube or can having a coating composition
KR1020187023269A KR102258413B1 (ko) 2016-01-15 2017-01-13 하이드록시 작용성 알킬 폴리우레아 가교제
EP17700092.4A EP3402849B1 (en) 2016-01-15 2017-01-13 Monobloc aerosol tube or can having a coating composition
RU2018129474A RU2737890C2 (ru) 2016-01-15 2017-01-13 Отверждение карбодиимидом композиций покрытия, предназначенных для упаковывания
PCT/US2017/013340 WO2017123873A1 (en) 2016-01-15 2017-01-13 Hydroxy functional alkyl polyurea containing compositions
CA3011232A CA3011232A1 (en) 2016-01-15 2017-01-13 Hydroxy functional alkyl polyurea crosslinkers
KR1020187023268A KR20180103978A (ko) 2016-01-15 2017-01-13 열경화성 수지 및 열가소성 수지를 포함하는 코팅 조성물
PCT/IB2017/050189 WO2017122170A1 (en) 2016-01-15 2017-01-13 A coating composition comprising a powder dispersed in a liquid carrier
RU2018129521A RU2706629C1 (ru) 2016-01-15 2017-01-13 Сшивающие агенты гидроксифункциональные алкилполимочевины
CN202211464279.XA CN115851042A (zh) 2016-01-15 2017-01-13 一种包含热固性树脂和热塑性树脂的涂料组合物
EP17702947.7A EP3402853A1 (en) 2016-01-15 2017-01-13 A coating composition comprising a powder dispersed in a liquid carrier
CA3011362A CA3011362A1 (en) 2016-01-15 2017-01-13 Hydroxy functional alkyl polyurea containing compositions
MX2018008547A MX2018008547A (es) 2016-01-15 2017-01-13 Curado de carbodiimida para composiciones de revestimiento de envases.
CN201780006634.XA CN108463516B (zh) 2016-01-15 2017-01-13 羟基官能化烷基聚脲交联剂
EP17704343.7A EP3402833A1 (en) 2016-01-15 2017-01-13 Hydroxy functional alkyl polyurea containing compositions
KR1020187023271A KR102170011B1 (ko) 2016-01-15 2017-01-13 하이드록시 작용성 알킬 폴리우레아 함유 조성물
KR1020187023266A KR102188399B1 (ko) 2016-01-15 2017-01-13 코팅 조성물을 패키징하기 위한 카보다이이미드 경화
PCT/US2017/013454 WO2017123955A1 (en) 2016-01-15 2017-01-13 Hydroxy functional alkyl polyurea crosslinkers
EP17704345.2A EP3402848A1 (en) 2016-01-15 2017-01-13 Hydroxy functional alkyl polyurea crosslinkers
KR1020217000080A KR102432704B1 (ko) 2016-01-15 2017-01-13 열경화성 수지 및 열가소성 수지를 포함하는 코팅 조성물
AU2017206969A AU2017206969A1 (en) 2016-01-15 2017-01-13 Monobloc aerosol tube or can having a coating composition
CN202110911842.2A CN113831823A (zh) 2016-01-15 2017-01-13 含羟基官能化烷基聚脲的组合物
EP17702946.9A EP3402850A1 (en) 2016-01-15 2017-01-13 A coating composition comprising a thermoset resin and a thermoplastic resin
CA3011325A CA3011325A1 (en) 2016-01-15 2017-01-13 Carbodiimide curing for packaging coating compositions
CN201780006633.5A CN108463520A (zh) 2016-01-15 2017-01-13 包含分散在液体载体中的粉末的涂料组合物
EP20206266.7A EP3822322A1 (en) 2016-01-15 2017-01-13 Monobloc aerosol tube or can having a coating composition
KR1020187023276A KR20180102635A (ko) 2016-01-15 2017-01-13 액체 담체에 분산된 분말을 포함하는 코팅 조성물
RU2018129517A RU2710431C1 (ru) 2016-01-15 2017-01-13 Цельная аэрозольная туба или баллон, содержащие композицию покрытия
US16/069,662 US10738216B2 (en) 2016-01-15 2017-01-13 Carbodiimide curing for packaging coating compositions
PCT/EP2017/050724 WO2017121879A1 (en) 2016-01-15 2017-01-13 Monobloc aerosol tube or can having a coating composition
ES17738272T ES2935010T3 (es) 2016-01-15 2017-01-13 Curado de carbodiimida para composiciones de recubrimiento de empaque
RU2018129499A RU2733716C2 (ru) 2016-01-15 2017-01-13 Композиции, содержащие гидроксифункциональную алкилполимочевину
AU2017207935A AU2017207935B2 (en) 2016-01-15 2017-01-13 Hydroxy functional alkyl polyurea crosslinkers
CN201780006573.7A CN108473795A (zh) 2016-01-15 2017-01-13 一种包含热固性树脂和热塑性树脂的涂料组合物
CA3011278A CA3011278A1 (en) 2016-01-15 2017-01-13 Monobloc aerosol tube or can having a coating composition
MX2018008548A MX2018008548A (es) 2016-01-15 2017-01-13 Reticulantes de alquil poliurea hidroxilo funcional.
CN201780006465.XA CN108473645B (zh) 2016-01-15 2017-01-13 含羟基官能化烷基聚脲的组合物
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US16/069,587 US10858536B2 (en) 2016-01-15 2017-01-13 Coating composition comprising a thermoset resin and a thermoplastic resin
KR1020187023299A KR102182370B1 (ko) 2016-01-15 2017-01-13 모노블록 에어로졸 튜브 또는 캔, 및 상기 튜브 및 캔을 제공하는 방법
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AU2017208147A AU2017208147B2 (en) 2016-01-15 2017-01-13 Carbodiimide curing for packaging coating compositions
PCT/IB2017/050191 WO2017122171A2 (en) 2016-01-15 2017-01-13 Carbodiimide curing for packaging coating compositions
CN201780006468.3A CN108699202A (zh) 2016-01-15 2017-01-13 用于包装涂料组合物的碳二酰亚胺固化
TW106101461A TW201741284A (zh) 2016-01-15 2017-01-16 含羥基官能性烷基聚脲之組合物
TW106101460A TW201734087A (zh) 2016-01-15 2017-01-16 羥基官能性烷基聚脲交聯劑
MX2023004360A MX2023004360A (es) 2016-01-15 2018-07-11 Reticulantes de alquil poliurea hidroxilo funcional.
US17/086,973 US11286401B2 (en) 2016-01-15 2020-11-02 Coating composition comprising a thermoset resin and a thermoplastic resin
US17/529,409 US20220073783A1 (en) 2016-01-15 2021-11-18 Hydroxy functional alkyl polyurea crosslinkers

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US16/069,561 Continuation US10738215B2 (en) 2016-01-15 2017-01-13 Monobloc aerosol tube or can having a coating composition
US16/069,785 Continuation US10723913B2 (en) 2016-01-15 2017-01-13 Hydroxy functional alkyl polyurea containing compositions
PCT/US2017/013454 Continuation WO2017123955A1 (en) 2016-01-15 2017-01-13 Hydroxy functional alkyl polyurea crosslinkers
US16/069,580 Continuation US10858535B2 (en) 2016-01-15 2017-01-13 Coating composition comprising a powder dispersed in a liquid carrier
US16/069,662 Continuation US10738216B2 (en) 2016-01-15 2017-01-13 Carbodiimide curing for packaging coating compositions
PCT/IB2017/050188 Continuation WO2017122169A1 (en) 2016-01-15 2017-01-13 A coating composition comprising a thermoset resin and a thermoplastic resin
US16/069,587 Continuation US10858536B2 (en) 2016-01-15 2017-01-13 Coating composition comprising a thermoset resin and a thermoplastic resin

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US16/069,662 Active 2036-04-09 US10738216B2 (en) 2016-01-15 2017-01-13 Carbodiimide curing for packaging coating compositions
US16/069,785 Active US10723913B2 (en) 2016-01-15 2017-01-13 Hydroxy functional alkyl polyurea containing compositions
US16/069,736 Active 2036-11-12 US11203701B2 (en) 2016-01-15 2017-01-13 Hydroxy functional alkyl polyurea crosslinkers
US16/069,580 Active 2036-04-26 US10858535B2 (en) 2016-01-15 2017-01-13 Coating composition comprising a powder dispersed in a liquid carrier
US16/069,587 Active 2036-04-26 US10858536B2 (en) 2016-01-15 2017-01-13 Coating composition comprising a thermoset resin and a thermoplastic resin
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US16/069,785 Active US10723913B2 (en) 2016-01-15 2017-01-13 Hydroxy functional alkyl polyurea containing compositions
US16/069,736 Active 2036-11-12 US11203701B2 (en) 2016-01-15 2017-01-13 Hydroxy functional alkyl polyurea crosslinkers
US16/069,580 Active 2036-04-26 US10858535B2 (en) 2016-01-15 2017-01-13 Coating composition comprising a powder dispersed in a liquid carrier
US16/069,587 Active 2036-04-26 US10858536B2 (en) 2016-01-15 2017-01-13 Coating composition comprising a thermoset resin and a thermoplastic resin
US17/529,409 Abandoned US20220073783A1 (en) 2016-01-15 2021-11-18 Hydroxy functional alkyl polyurea crosslinkers

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Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:KURTZ, CHRISTOPHER P;DUDIK, JOHN M;SWARUP, SHANTI;AND OTHERS;SIGNING DATES FROM 20160118 TO 20160119;REEL/FRAME:037531/0958

STCB Information on status: application discontinuation

Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION