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US20120301647A1 - Phosphatized polyesters and coating compositions containing the same - Google Patents

Phosphatized polyesters and coating compositions containing the same Download PDF

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Publication number
US20120301647A1
US20120301647A1 US13/113,130 US201113113130A US2012301647A1 US 20120301647 A1 US20120301647 A1 US 20120301647A1 US 201113113130 A US201113113130 A US 201113113130A US 2012301647 A1 US2012301647 A1 US 2012301647A1
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US
United States
Prior art keywords
coating composition
acid
coating
weight
polyester
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
US13/113,130
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English (en)
Inventor
Youssef Moussa
Claudia Knotts
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 US13/113,130 priority Critical patent/US20120301647A1/en
Assigned to PPG INDUSTRIES OHIO, INC. reassignment PPG INDUSTRIES OHIO, INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: KNOTTS, Claudia, MOUSSA, YOUSSEF
Priority to AU2012258930A priority patent/AU2012258930B2/en
Priority to CN201280031784.3A priority patent/CN103619718B/zh
Priority to KR1020177002703A priority patent/KR102143268B1/ko
Priority to PL12726958T priority patent/PL2714535T3/pl
Priority to ES12726958.7T priority patent/ES2554233T3/es
Priority to HK14107821.4A priority patent/HK1194344B/zh
Priority to BR112013030020A priority patent/BR112013030020A2/pt
Priority to RU2013156831/05A priority patent/RU2571137C2/ru
Priority to MYPI2013004189A priority patent/MY161368A/en
Priority to MX2013013652A priority patent/MX354114B/es
Priority to CA2836909A priority patent/CA2836909C/en
Priority to NZ618116A priority patent/NZ618116B2/en
Priority to PCT/US2012/038965 priority patent/WO2012162301A1/en
Priority to DK12726958.7T priority patent/DK2714535T3/en
Priority to KR1020137033985A priority patent/KR20140013092A/ko
Priority to SG2013085790A priority patent/SG195058A1/en
Priority to PT127269587T priority patent/PT2714535E/pt
Priority to EP12726958.7A priority patent/EP2714535B1/en
Priority to TW101118415A priority patent/TWI461495B/zh
Publication of US20120301647A1 publication Critical patent/US20120301647A1/en
Priority to US13/923,404 priority patent/US9321935B2/en
Priority to ZA2013/08774A priority patent/ZA201308774B/en
Priority to US15/018,882 priority patent/US10703931B2/en
Priority to US15/372,557 priority patent/US10280332B2/en
Abandoned legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
    • C09D167/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • 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
    • C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
    • C09D133/04—Homopolymers or copolymers of esters
    • C09D133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C09D133/08—Homopolymers or copolymers of acrylic acid esters
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D1/00—Processes for applying liquids or other fluent materials
    • B05D1/02—Processes for applying liquids or other fluent materials performed by spraying
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
    • B05D3/02—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by baking
    • B05D3/0218—Pretreatment, e.g. heating the substrate
    • B05D3/0236—Pretreatment, e.g. heating the substrate with ovens
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • 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
    • B05D7/22—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 internal surfaces, e.g. of tubes
    • B05D7/227—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 internal surfaces, e.g. of tubes of containers, cans or the like
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • 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
    • B05D7/24—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 for applying particular liquids or other fluent materials
    • 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
    • B65D25/00—Details of other kinds or types of rigid or semi-rigid containers
    • B65D25/14—Linings or internal coatings
    • 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
    • B65D25/00—Details of other kinds or types of rigid or semi-rigid containers
    • B65D25/34—Coverings or external coatings
    • 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
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
    • C08G63/692—Polyesters containing atoms other than carbon, hydrogen and oxygen containing phosphorus
    • 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
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
    • C08G63/692—Polyesters containing atoms other than carbon, hydrogen and oxygen containing phosphorus
    • C08G63/6924—Polyesters containing atoms other than carbon, hydrogen and oxygen containing phosphorus derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/6926—Dicarboxylic acids and dihydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
    • 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
    • C09D201/00—Coating compositions based on unspecified macromolecular compounds
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/13—Hollow or container type article [e.g., tube, vase, etc.]
    • Y10T428/1352—Polymer or resin containing [i.e., natural or synthetic]

Definitions

  • the present invention relates to phosphatized polyesters and to coating compositions containing such polyesters.
  • the compositions are useful for coating containers of various sorts such as food and beverage containers.
  • a wide variety of coatings have been used to coat the surfaces of food and beverage containers.
  • metal cans are sometimes coated using coil coating or sheet coating operations, that is, a plane or coil or sheet of a suitable substrate, for example, steel or aluminum, is coated with a suitable composition and cured.
  • the coated substrate is then formed into the canned body or canned end.
  • the coating composition may be applied, for example, by spraying and dipping, to the formed can and then cured.
  • Coatings for food and beverage containers should preferably be capable of high speed application to the substrate and provide the necessary properties when cured to perform in a demanding end use.
  • the coating should be safe for food contact and have excellent adhesion to the substrate.
  • the coated article comprises:
  • acrylic and “acrylate” are used interchangeably (unless to do so would alter the intended meaning) and include acrylic acids, anhydrides, and derivatives thereof, such as their C 1 -C 5 alkyl esters, lower alkyl-substituted acrylic acids, e.g., C 1 -C 2 substituted acrylic acids, such as methacrylic acid, ethacrylic acid, etc., and their C 1 -C 5 alkyl esters, unless clearly indicated otherwise.
  • the terms “(meth)acrylic” or “(meth)acrylate” are intended to cover both the acrylic/acrylate and methacrylic/methacrylate forms of the indicated material, e.g., a (meth)acrylate monomer.
  • acrylic polymer refers to polymers prepared from one or more acrylic monomers.
  • a coating composition that comprises “a” polymer can be interpreted to mean the coating composition includes “one or more” polymers.
  • the phosphatized polyester is prepared by reacting a precursor polyester resin with a phosphorus acid.
  • the polyester resin contains both hydroxyl functionality and carboxylic acid functionality.
  • the polyester resin typically has a hydroxyl number of 20 to 75 mg KOH per gram of polyester resin and an acid value of 15 to 20 mg KOH per gram of polyester resin; each measured on a non-volatile solids basis.
  • the polyester resins have number average molecular weights (Mn) of 2000 to 10,000 g/mole.
  • the polyester resins are typically prepared from a mixture of the alpha, beta-ethylenically unsaturated polycarboxylic acid, usually with an aromatic and/or aliphatic polycarboxylic acid, and a polyol component, typically a mixture of a diol and triol.
  • the polyol and polycarboxylic acid are combined in desired proportions and chemically reacted using standard esterification (condensation) procedures to provide a polyester having both hydroxyl and carboxylic acid groups in the polyester resin.
  • a triol is typically used to provide a branched, as opposed to linear, polyester.
  • polycarboxylic acids or anhydrides include, but are not limited to, maleic anhydride, maleic acid, fumaric acid, itaconic acid, phthalic acid, phthalic anhydride, isophthalic acid, trimellitic anhydride, terephthalic acid, naphthalene dicarboxylic acid, adipic acid, azelaic acid, succinic acid, sebacic acid and various mixtures thereof.
  • the aromatic and/or aliphatic polycarboxylic acid is used in amounts up to 70 percent by weight, typically 50 to 65 percent by weight based on total weight of the polycarboxylic acid or anhydride.
  • suitable diols, triols and polyols include, but are not limited to, ethylene glycol, propylene glycol, 1,3-propanediol, glycerol, diethylene glycol, dipropylene glycol, triethylene glycol, trimethylolpropane, trimethylolethane, tripropylene glycol, neopentyl glycol, pentaerythritol, 1,4-butanediol, trimethylol propane, hexylene glycol, cyclohexane dimethanol, and polyethylene or polypropylene glycol.
  • the polyol component is a mixture of a diol and a triol.
  • the weight ratio of diol to triol typically ranges from 0.5 to 10 to 1.
  • the equivalent ratio of polyol component to polycarboxylic acid is from 0.9 to 1.1 to 1.0.
  • the phosphorus acid which is reacted with the polyester resin can be a phosphinic acid, a phosphonic acid or is preferably phosphoric acid.
  • the phosphoric acid can be in the form of an aqueous solution, for example, an 85 percent by weight aqueous solution, or can be 100 percent phosphoric acid or super phosphoric acid.
  • the acid is provided in amounts of about 0.2-0.5 equivalents of phosphoric acid per hydroxyl equivalent of the polyester resin, i.e., 0.2-0.45 P—OH groups per hydroxyl group.
  • the reaction of the phosphorus acid with the polyester resin is typically conducted in organic solvent.
  • the organic solvent is typically an aromatic solvent, a ketone or an ester having a boiling point of about 65 to 250° C.
  • suitable solvents include methyl ethyl ketone, methyl isobutyl ketone, butyl glycol acetate and methoxypropyl acetate.
  • the organic solvent for the reaction is typically present in amounts of about 20 to 50 percent by weight based on total weight of phosphorus acid, polyester resin and organic solvent.
  • the reactants and the organic solvent are typically mixed at a temperature between 50° C. to 95° C. and once the reactants are contacted, the reaction mixture is maintained at a temperature preferably between 90° C. to 200° C. The reaction typically is allowed to proceed for a period of about 45 minutes to 6 hours.
  • the phosphatized polyester is used, typically in minor amounts, in a coating composition where it provides for improved adhesion of the resultant coating to the substrate.
  • the phosphatized polyester is typically present in the coating composition in amounts up to 10 percent by weight, preferably 0.1 to 5 percent by weight based on weight of resin solids in the coating composition. Amounts less than 0.1 percent by weight result in inferior adhesion of the coating composition to the substrate where amounts greater than 10 percent by weight provide no additional advantage.
  • the coating composition comprises a resinous vehicle, organic solvent and further optional ingredients.
  • the resinous vehicle is preferably an acrylic polymer and/or a polyester polymer.
  • the acrylic polymer is preferably a polymer derived from one or more acrylic monomers. Furthermore, blends of acrylic polymers can be used. Preferred monomers are acrylic acid, methyl acrylate, ethyl acrylate, propyl acrylate, butyl acrylate, penta acrylate, hexyl acrylate, methacrylic acid, methyl methacrylate, ethyl methacrylate, propyl methacrylate, butyl methacrylate, penta methacrylate and hexyl methacrylate.
  • the acrylic polymer may also contain hydroxyl groups which typically are derived from hydroxy-substituted acrylic or methacrylic acid esters. Examples include hydroxyethyl acrylate and hydroxypropyl methacrylate.
  • the weight average molecular weight (Mw) of the acrylic polymer component is preferably at least 5,000 g/mole, more preferably from 15,000 to 100,000 g/mole.
  • the acrylic polymer typically has an acid value of 30 to 70, such as 40 to 60 mg KOH/g; a hydroxyl value of 0 to 100, such as 0 to 70 mg of KOH/g and a glass transition temperature (Tg) of ⁇ 20 to +100° C., such as +20 to +70° C.
  • polyester polymers are prepared by processes well known in the art as mentioned above comprising the condensation polymerization reaction of one or more polycarboxylic acids with one or more polyols.
  • suitable polycarboxylic acids are phthalic acid, isophthalic acid, terephthalic acid, 1,4-cyclohexane dicarboxylic acid, succinic acid, sebacic acid, methyltetrahydrophthalic acid, methyl hexahydrophthalic acid, tetrahydrophthalic acid, dodecane dioic acid, adipic acid, azelaic acid, naphthylene dicarboxylic acid, pyromellitic acid, dimer fatty acids and/or trimellitic acid.
  • the polyol component is, for example, selected from diols or triols.
  • suitable polyols include ethylene glycol, 1,3-propanediol, diethylene glycol, dipropylene glycol, triethylene glycol, 1,4-butanediol, 2-methyl-1,3-propanediol, 1,4-cyclohexane dimethanol, 1,6-hexanediol, neopentyl glycol, trimethylolpropane and glycerol.
  • the polyester polymer preferably has a number average molecular weight between 1000 and 20,000 g/mole.
  • Suitable curing agents are phenolplasts or phenol-formaldehyde resins and aminoplast or triazine-formaldehyde resins.
  • the phenol-formaldehyde resins are preferably of the resol type. Examples of suitable phenols are phenol itself, butyl phenol, xylenol and cresol. Cresol-formaldehyde resins, the types typically etherified with butanol, are often used.
  • aminoplast resins are those which are formed by reacting a triazine such as melamine or benzoguanamine with formaldehyde.
  • these condensates are etherified typically with methanol, ethanol, butanol including mixtures thereof.
  • MAPRENAL® such as MAPRENAL MF980
  • CYMEL® such as CYMEL 303 and CYMEL 1128, available from Cytec Industries.
  • the acrylic polymer and/or the polyester polymer is used in amounts of 40 to 90, preferably 30 to 70 percent by weight, and the crosslinking agent is present in amounts of 5 to 50, preferably 20 to 40 percent by weight, the percentages by weight being based on the weight of total resin solids in the coating composition.
  • the coating composition will contain a diluent, such as water, or an organic solvent or a mixture of water and organic solvent to dissolve or disperse the resinous binder and the phosphated polyester.
  • a diluent such as water, or an organic solvent or a mixture of water and organic solvent to dissolve or disperse the resinous binder and the phosphated polyester.
  • the organic solvent is selected to have sufficient volatility to evaporate essentially entirely from the coating composition during the curing process such as during heating from 175-205° C. for about 5 to 15 minutes.
  • suitable organic solvents are aliphatic hydrocarbons such as mineral spirits and high flash point VM&P naphtha; aromatic hydrocarbons such as benzene, toluene, xylene and solvent naphtha 100, 150, 200 and the like; alcohols, for example, ethanol, n-propanol, isopropanol, n-butanol and the like; ketones such as acetone, cyclohexanone, methylisobutyl ketone and the like; esters such as ethyl acetate, butyl acetate, and the like; glycols such as butyl glycol, glycol ethers such as methoxypropanol and ethylene glycol monomethyl ether and ethylene glycol monobutyl ether and the like.
  • aliphatic hydrocarbons such as mineral spirits and high flash point VM&P naphtha
  • aromatic hydrocarbons such as benzene, toluene, xylene and solvent nap
  • the resinous vehicle typically has acid groups, such as acid functional acrylic polymers, that are at least partially neutralized with an amine to assist in the dispersion or dissolution in the aqueous medium.
  • acid groups such as acid functional acrylic polymers
  • the diluents are used in the coating compositions in amounts of about 20 to 83, preferably 30 to 70 percent by weight based on total weight of the coating composition.
  • Adjuvant resins such as polyether polyols and polyurethane polyols may be included in the coating compositions to maximize certain properties of the resultant coating.
  • the adjuvant resin is used in amounts of up to 50, typically 2-50 percent by weight based on weight of resin solids of the coating composition.
  • Another optional ingredient that is typically present in the coating composition is a catalyst to increase the rate of cure or crosslinking of the coating compositions.
  • acid catalyst may be used and is typically present in amounts of about 0.05 to 5 percent by weight.
  • suitable catalyst are dodecyl benzene sulfonic acid, methane sulfonic acid, paratoluene sulfonic acid, dinonyl naphthalene disulfonic acid and phenyl phosphonic acid. It has been found that the amount of acid catalyst in the coating compositions of the invention is not as great as would normally be expected due to the presence of the phosphated polyester. This reaction product is acidic and has been found to contribute to the cure of the coating composition.
  • pigment such as titanium dioxide. If used, the pigment is present in the coating compositions in amounts no greater than 70 percent by weight, preferably no greater than 40 percent by weight based on total weight of solids in the coating composition.
  • Surfactants can optionally be added to the coating composition to aid in flow and wetting of the substrate.
  • suitable surfactants include, but are not limited to, nonyl phenol polyether and salts. If used, the surfactant is present in amounts of at least 0.01 percent and no greater than 10 percent based on weight of resin solids in the coating composition.
  • compositions used in the practice of the invention are substantially free, may be essentially free and may be completely free of bisphenol A and derivatives or residues thereof, including bisphenol A (“BPA”) and bisphenol A diglycidyl ether (“BADGE”).
  • BPA bisphenol A
  • BADGE bisphenol A diglycidyl ether
  • Such compositions are sometimes referred to as “BPA non intent” because BPA, including derivatives or residues thereof are not intentionally added but may be present in trace amounts because of unavoidable contamination from the environment.
  • the compositions can also be substantially free and may be essentially free and may be completely free of Bisphenol F and derivatives or residues thereof, including bisphenol F and bisphenol F diglycidyl ether (“BPFG”).
  • compositions 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.
  • the coating compositions of the present invention can be applied to containers of all sorts and are particularly well adapted for use on food and beverage cans (e.g., two-piece cans, three-piece cans, etc.). Besides food and beverage containers, the coating compositions can be applied to containers for aerosol applications such as deodorant and hair spray.
  • Two-piece cans are manufactured by joining a can body (typically a drawn metal body) with a can end (typically a drawn metal end).
  • the coatings of the present invention are suitable for use in food or beverage contact situations and may be used on the inside or outside of such cans. They are suitable for spray applied, liquid coatings, wash coatings, sheet coatings, over varnish coatings and side seam coatings.
  • Spray coating includes the introduction of the coating composition into the inside of a preformed packaging container.
  • Typical preformed packaging containers suitable for spray coating include food cans, beer and beverage containers, and the like.
  • the spray preferably utilizes a spray nozzle capable of uniformly coating the inside of the preformed packaging container.
  • the sprayed preformed container is then subjected to heat to remove the residual solvents and harden the coating.
  • a coil coating is described as the coating, typically by a roll coating application, of a continuous coil composed of a metal (e.g., steel or aluminum). Once coated, the coating coil is subjected to a short thermal, ultraviolet, and/or electromagnetic curing cycle, for hardening (e.g., drying and curing) of the coating.
  • Coil coatings provide coated metal (e.g., steel and/or aluminum) substrates that can be fabricated into formed articles, such as two-piece drawn food cans, three-piece food cans, food can ends, drawn and ironed cans, beverage can ends, and the like.
  • a wash coating is commercially described as the coating of the exterior of two-piece drawn and ironed (“D&I”) cans with a thin layer of protectant coating.
  • the exterior of these D&I cans are “wash-coated” by passing preformed two-piece D&I cans under a curtain of a coating composition.
  • the cans are inverted, that is, the open end of the can is in the “down” position when passing through the curtain.
  • This curtain of coating composition takes on a “waterfall-like” appearance. Once these cans pass under this curtain of coating composition, the liquid coating material effectively coats the exterior of each can. Excess coating is removed through the use of an “air knife”.
  • each can is passed through a thermal, ultraviolet, and/or electromagnetic curing oven to harden (e.g., dry and cure) the coating.
  • the residence time of the coated can within the confines of the curing oven is typically from 1 minute to 5 minutes.
  • the curing temperature within this oven will typically range from 150° C. to 220° C.
  • a sheet coating is described as the coating of separate pieces of a variety of materials (e.g., steel or aluminum) that have been pre-cut into square or rectangular “sheets”. Typical dimensions of these sheets are approximately one square meter.
  • each sheet is cured. Once hardened (e.g., dried and cured), the sheets of the coated substrate are collected and prepared for subsequent fabrication.
  • Sheet coatings provide coated metal (e.g., steel or aluminum) substrate that can be successfully fabricated into formed articles, such as two-piece drawn food cans, three-piece food cans, food can ends, drawn and ironed cans, beverage can ends, and the like.
  • a side seam coating is described as the spray application of a liquid coating over the welded area of formed three-piece food cans.
  • a rectangular piece of coated substrate is formed into a cylinder.
  • the formation of the cylinder is rendered permanent due to the welding of each side of the rectangle via thermal welding.
  • each can typically requires a layer of liquid coating, which protects the exposed “weld” from subsequent corrosion or other effects to the contained foodstuff.
  • the liquid coatings that function in this role are termed “side seam stripes”.
  • Typical side seam stripes are spray applied and cured quickly via residual heat from the welding operation in addition to a small thermal, ultraviolet, and/or electromagnetic oven.
  • a phosphatized polyester resin was prepared from the following mixture of ingredients:
  • the mixture When the acid value of the mixture dropped to about 13.00 mg of KOH/g, the mixture was cooled to about 160° C. and then the Aromatic 100 solvent (i.e., an aromatic hydrocarbon solvent blend commercially available from Exxon Mobil) was incorporated for azeotropic distillation of water evolved as a condensate by-product. Thereafter, the phosphoric acid solution and water were added and the azeotropic distillation of water was continued until the acid value of the mixture dropped to below 20 mg of KOH/g. The resulting phosphatized polyester resin was then dissolved in the 2-butoxyethanol and monobutyl ether of diethylene glycol to produce a composition which was about 50 percent by weight solids.
  • the Aromatic 100 solvent i.e., an aromatic hydrocarbon solvent blend commercially available from Exxon Mobil
  • the number average molecular weight of the resulting phosphatized polyester was about 4500, the acid value was about 20 and the hydroxyl value was about 45.
  • a series of container coating compositions were prepared based on a binder comprising a polyester polyol and aminoplast and phenolplast curing agents.
  • One composition contained a phosphatized polyester adhesion promoter
  • a second composition contained the bisphenol A diglycidyl ether (BADGE) adhesion promoter
  • the third composition contained no adhesion promoter.
  • Adhesion testing is performed to assess whether the coating adheres to the coated substrate. The adhesion test was performed according to ASTM D3359-Test Method B, using Scotch 610 tape, available from 3M Company of Saint Paul, Minnesota. Adhesion is generally rated on a scale of 0-100 where a rating of “100” indicates no adhesion failure and a rating of “90” indicates 90% of the coating remains adhered.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Materials Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Mechanical Engineering (AREA)
  • Paints Or Removers (AREA)
  • Application Of Or Painting With Fluid Materials (AREA)
  • Details Of Rigid Or Semi-Rigid Containers (AREA)
US13/113,130 2011-05-23 2011-05-23 Phosphatized polyesters and coating compositions containing the same Abandoned US20120301647A1 (en)

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Application Number Priority Date Filing Date Title
US13/113,130 US20120301647A1 (en) 2011-05-23 2011-05-23 Phosphatized polyesters and coating compositions containing the same
EP12726958.7A EP2714535B1 (en) 2011-05-23 2012-05-22 Phosphatized polyesters and coating compositions containing the same
NZ618116A NZ618116B2 (en) 2011-05-23 2012-05-22 Phosphatized polyesters and coating compositions containing the same
DK12726958.7T DK2714535T3 (en) 2011-05-23 2012-05-22 Phosphated polyesters and coatings containing the same
KR1020177002703A KR102143268B1 (ko) 2011-05-23 2012-05-22 인산화된 폴리에스터 및 이를 함유하는 코팅 조성물
PL12726958T PL2714535T3 (pl) 2011-05-23 2012-05-22 Fosforanowane poliestry i zawierające je kompozycje powłokowe
ES12726958.7T ES2554233T3 (es) 2011-05-23 2012-05-22 Poliésteres fosfatados y composiciones de revestimiento que los contienen
HK14107821.4A HK1194344B (zh) 2011-05-23 2012-05-22 含磷的酸酸化的聚酯和含有它的涂料组合物
BR112013030020A BR112013030020A2 (pt) 2011-05-23 2012-05-22 composição de revestimento e artigo revestido
RU2013156831/05A RU2571137C2 (ru) 2011-05-23 2012-05-22 Фосфатированные полиэфирные пластики и покрывающие составы, содержащие данные соединения
MYPI2013004189A MY161368A (en) 2011-05-23 2012-05-22 Phosphatized polyesters and coating compositions containing the same
MX2013013652A MX354114B (es) 2011-05-23 2012-05-22 Poliesteres fosfatados y composiciones de revestimiento que los contienen.
CA2836909A CA2836909C (en) 2011-05-23 2012-05-22 Phosphatized polyesters and coating compositions containing the same
AU2012258930A AU2012258930B2 (en) 2011-05-23 2012-05-22 Phosphatized polyesters and coating compositions containing the same
PCT/US2012/038965 WO2012162301A1 (en) 2011-05-23 2012-05-22 Phosphatized polyesters and coating compositions containing the same
CN201280031784.3A CN103619718B (zh) 2011-05-23 2012-05-22 含磷的酸酸化的聚酯和含有它的涂料组合物
KR1020137033985A KR20140013092A (ko) 2011-05-23 2012-05-22 인산화된 폴리에스터 및 이를 함유하는 코팅 조성물
SG2013085790A SG195058A1 (en) 2011-05-23 2012-05-22 Phosphatized polyesters and coating compositions containing the same
PT127269587T PT2714535E (pt) 2011-05-23 2012-05-22 Poliésteres fosfatizados e composições de revestimento contendo os mesmos
TW101118415A TWI461495B (zh) 2011-05-23 2012-05-23 磷酸化聚酯及含彼之塗覆組合物
US13/923,404 US9321935B2 (en) 2011-05-23 2013-06-21 Container coating compositions
ZA2013/08774A ZA201308774B (en) 2011-05-23 2013-11-21 Phosphatized polyesters and coating compositions containing the same
US15/018,882 US10703931B2 (en) 2011-05-23 2016-02-09 Container coating compositions
US15/372,557 US10280332B2 (en) 2011-05-23 2016-12-08 Phosphatized polyesters and coating compositions containing the same

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AU (1) AU2012258930B2 (zh)
BR (1) BR112013030020A2 (zh)
CA (1) CA2836909C (zh)
DK (1) DK2714535T3 (zh)
ES (1) ES2554233T3 (zh)
MX (1) MX354114B (zh)
MY (1) MY161368A (zh)
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PT (1) PT2714535E (zh)
RU (1) RU2571137C2 (zh)
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EP2963092A1 (en) 2014-06-30 2016-01-06 PPG Industries Ohio Inc. A coating composition
US9409219B2 (en) 2011-02-07 2016-08-09 Valspar Sourcing, Inc. Compositions for containers and other articles and methods of using same
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WO2017003922A1 (en) * 2015-07-01 2017-01-05 Ppg Industries Ohio, Inc. Aqueous-based coating composition containing a polyanhydride
US9617446B2 (en) 2010-12-29 2017-04-11 Akzo Nobel Coatings International B.V. Adhesion promoter resin compositions and coating compositions having the adhesion promoter resin compositions
US9650176B2 (en) 2012-02-17 2017-05-16 Valspar Sourcing, Inc. Methods and materials for the functionalization of polymers and coatings including functionalized polymer
WO2017123975A1 (en) 2016-01-15 2017-07-20 Ppg Industries Ohio, Inc. Containers coated with compositions having enhanced heat-aging properties
US20170225830A1 (en) * 2014-10-06 2017-08-10 Toyo Seikan Group Holdings, Ltd. Coated metal sheet further covered with an organic resin, can body and can lid made therefrom
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MX2018008500A (es) * 2016-01-15 2018-08-16 Ppg Ind Ohio Inc Tubo o lata de aerosol monobloque que tiene una composicion de revestimiento.
US20170204289A1 (en) 2016-01-15 2017-07-20 Ppg Industries Ohio, Inc. Hydroxy functional alkyl polyurea
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US10752799B2 (en) 2018-02-07 2020-08-25 Ppg Industries Ohio, Inc. Self-curing coating compositions
US20210253887A1 (en) 2018-05-08 2021-08-19 Agfa-Gevaert Nv Conductive inks
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US20210189170A1 (en) 2018-07-25 2021-06-24 Ppg Industries Ohio, Inc. A product coated with an aqueous or powder coating composition comprising an acrylic polyester resin
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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4960600A (en) * 1988-12-21 1990-10-02 The Procter & Gamble Co. Polyol polyesters as a protective moisture barrier for foods
US20020086168A1 (en) * 1999-07-30 2002-07-04 Sadvary Richard J Coating compositions having improved adhesion, coated substrates and methods related thereto

Family Cites Families (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3415766A (en) * 1966-12-09 1968-12-10 Lubrizol Corp Coating compositions comprising in combination a siccative organic coating composition and a phosphorus-containing composition
CA992240A (en) * 1970-12-30 1976-06-29 Robert Demajistre Method of adhering novel polyester resins to substrates
DE3361701D1 (en) * 1982-07-29 1986-02-13 Vianova Kunstharz Ag Process for the preparation of polyester resins containing phosphoric-acid groups, and their use
NL1005841C2 (nl) * 1997-04-18 1998-10-20 Dsm Nv Can- en coilcoatingharsen.
US5859154A (en) * 1997-09-26 1999-01-12 Ppg Industries, Inc. Resinous composition of phosphatized polyester polymers and coating compositions for improved adhesion
WO1999031186A1 (en) * 1997-12-17 1999-06-24 Ppg Industries Ohio, Inc. Flexible phosphatized polyester-urethane primers and improved coating systems including the same
US6458874B1 (en) * 2000-06-22 2002-10-01 Basf Corporation Coating compositions having improved direct to metal adhesion
WO2002072664A1 (en) * 2001-03-13 2002-09-19 Dsm Ip Assets B.V. Coating composition comprising a phosphatized polyester
US6534609B2 (en) * 2001-03-13 2003-03-18 Chevron Phillips Chemical Company Lp Method for making and using a metallocene catalyst system
US20040132895A1 (en) * 2002-08-30 2004-07-08 Ambrose Ronald R. Compositions and methods for coating food cans
US7745508B2 (en) * 2002-08-30 2010-06-29 Ppg Industries Ohio, Inc. Compositions and methods for coating food cans
CN101067066A (zh) * 2006-05-05 2007-11-07 罗门哈斯公司 酸官能含磷聚酯粉末组合物和由该组合物制备的粉末涂层
US8029894B2 (en) * 2006-08-18 2011-10-04 Ppg Industries Ohio, Inc. Multi-layer composites formed from compositions having improved adhesion
EP1964898A1 (en) * 2007-02-22 2008-09-03 Cytec Surface Specialties Austria GmbH Coating compositions for can coating comprising phenolic resins
US8084137B2 (en) * 2008-01-11 2011-12-27 The Sherwin-Williams Company Metal coating composition

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4960600A (en) * 1988-12-21 1990-10-02 The Procter & Gamble Co. Polyol polyesters as a protective moisture barrier for foods
US20020086168A1 (en) * 1999-07-30 2002-07-04 Sadvary Richard J Coating compositions having improved adhesion, coated substrates and methods related thereto

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US11130881B2 (en) 2010-04-16 2021-09-28 Swimc Llc Coating compositions for packaging articles and methods of coating
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US9617446B2 (en) 2010-12-29 2017-04-11 Akzo Nobel Coatings International B.V. Adhesion promoter resin compositions and coating compositions having the adhesion promoter resin compositions
US11634607B2 (en) 2011-02-07 2023-04-25 Swimc Llc Compositions for containers and other articles and methods of using same
US10294388B2 (en) 2011-02-07 2019-05-21 Swimc Llc Compositions for containers and other articles and methods of using same
US9409219B2 (en) 2011-02-07 2016-08-09 Valspar Sourcing, Inc. Compositions for containers and other articles and methods of using same
US11053409B2 (en) 2011-02-07 2021-07-06 Jeffrey Niederst Compositions for containers and other articles and methods of using same
US9650176B2 (en) 2012-02-17 2017-05-16 Valspar Sourcing, Inc. Methods and materials for the functionalization of polymers and coatings including functionalized polymer
US11383886B2 (en) 2012-02-17 2022-07-12 The Sherwin-Williams Company Methods and materials for the functionalization of polymers and coatings including functionalized polymer
US10703540B2 (en) 2012-02-17 2020-07-07 Valspar Sourcing, Inc. Methods and materials for the functionalization of polymers and coatings including functionalized polymer
US10894632B2 (en) 2012-08-09 2021-01-19 Swimc Llc Compositions for containers and other articles and methods of using same
US12043448B2 (en) 2012-08-09 2024-07-23 Swimc Llc Compositions for containers and other articles and methods of using same
US11628974B2 (en) 2012-08-09 2023-04-18 Swimc Llc Compositions for containers and other articles and methods of using same
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US11525018B2 (en) 2014-04-14 2022-12-13 Swimc Llc Methods of preparing compositions for containers and other articles and methods of using same
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US10745514B2 (en) 2014-04-14 2020-08-18 Swimc Llc Methods of preparing compositions for containers and other articles and methods of using same
EP2963092A1 (en) 2014-06-30 2016-01-06 PPG Industries Ohio Inc. A coating composition
US20170225830A1 (en) * 2014-10-06 2017-08-10 Toyo Seikan Group Holdings, Ltd. Coated metal sheet further covered with an organic resin, can body and can lid made therefrom
US10442889B2 (en) 2014-11-27 2019-10-15 Ppg Industries Ohio, Inc. Coating composition comprising a binder formed from polyester and a phosphorus acid
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WO2016174105A1 (en) * 2015-04-30 2016-11-03 Ppg Industries Ohio, Inc. Pull tabs for food and/or beverage cans
EP3088318A1 (en) * 2015-04-30 2016-11-02 PPG Industries Ohio, Inc. Pull tabs for food and/or beverage cans
WO2017003922A1 (en) * 2015-07-01 2017-01-05 Ppg Industries Ohio, Inc. Aqueous-based coating composition containing a polyanhydride
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US20210163780A1 (en) * 2018-07-25 2021-06-03 Ppg Industries Ohio, Inc. An acrylic polyester resin and an aqueous or powder coating composition containing the same
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US10280332B2 (en) 2019-05-07
TWI461495B (zh) 2014-11-21
KR102143268B1 (ko) 2020-08-28
WO2012162301A1 (en) 2012-11-29
TW201307494A (zh) 2013-02-16
CA2836909A1 (en) 2012-11-29
EP2714535B1 (en) 2015-09-30
ZA201308774B (en) 2016-01-27
CN103619718A (zh) 2014-03-05
HK1194344A1 (zh) 2014-10-17
PL2714535T3 (pl) 2016-02-29
SG195058A1 (en) 2013-12-30
CN103619718B (zh) 2016-04-13
RU2571137C2 (ru) 2015-12-20
CA2836909C (en) 2016-02-09
PT2714535E (pt) 2015-12-07
MY161368A (en) 2017-04-14
ES2554233T3 (es) 2015-12-17
MX354114B (es) 2018-02-08
KR20170016022A (ko) 2017-02-10
KR20140013092A (ko) 2014-02-04
US20170081549A1 (en) 2017-03-23
NZ618116A (en) 2015-06-26
AU2012258930B2 (en) 2015-06-11
DK2714535T3 (en) 2016-01-11
BR112013030020A2 (pt) 2016-09-13
EP2714535A1 (en) 2014-04-09

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