Classifications

• • 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
  • C08G18/67—Unsaturated compounds having active hydrogen
  • 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
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
  • C08F283/04—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polycarbonamides, polyesteramides or polyimides
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
  • C08F283/10—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polymers containing more than one epoxy radical per molecule
• • 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
  • C08G18/58—Epoxy resins
  • C08G18/584—Epoxy resins having nitrogen
• • 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
  • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
  • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
• • 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
  • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
  • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
  • C08G59/182—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing using pre-adducts of epoxy compounds with curing agents
  • C08G59/184—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing using pre-adducts of epoxy compounds with curing agents with amines
• • 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
  • C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
• • 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
• • 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
  • C09D179/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09D161/00 - C09D177/00
  • C09D179/02—Polyamines
• • 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
  • C09D5/44—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes for electrophoretic applications
  • C09D5/4473—Mixture of polymers
• • 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
  • C08G2270/00—Compositions for creating interpenetrating networks
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
  • C08L33/04—Homopolymers or copolymers of esters
  • C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
  • C08L33/10—Homopolymers or copolymers of methacrylic acid esters
  • C08L33/12—Homopolymers or copolymers of methyl methacrylate

Definitions

• a coating composition is sometimes applied as a film, which may include a carrier (e.g., water and/or organic solvent).
• the coating may be applied on a substrate by a process such as lamination, solution or dispersion coating, powder coating, electrocoating, spray coating, roll coating, or reverse roll coating.
• Coating compositions can also be applied as a film by extrusion in melt form through an extrusion coating die onto a substrate.
• the composition is preferably cured (and dried if the composition includes a carrier) without defects within a few seconds, as modern high speed coating lines heat the coated substrates rapidly to temperatures of up to 490° F.
• Epoxy resins are particularly desirable for use in protective surface coating compositions, e.g., as a vehicle or polymeric binder for optional pigments, fillers, and other additives.
• the epoxy resins advantageously provide properties such as toughness, flexibility, adhesion, and chemical resistance.
• the present invention provides a method of coating an article.
• the method includes the steps of applying the above-described coating composition to an article and hardening the coating composition to provide a coated article.
• the method includes the step of heating the coated article to provide a crosslinked coating.
• epoxy-amine material refers to the reaction product of an epoxy material (e.g., an epoxy resin) with an amine to provide an epoxy-amine material having increased (i.e., advanced) molecular weight compared to the starting epoxy material.
• the epoxy-amine material has residual epoxy functionality.
• Polymerization or “polymerizable” denotes the curing or cross-linking of the coating composition after a coated substrate is exposed to radiation (e.g., ultra-violet or electron beam), heat, or other means of initiating polymerization.
• radiation e.g., ultra-violet or electron beam
• Thermosettable or “thermoset” refers to a composition that is transformed into a gel structure by application of radiation and/or heat. A gel structure is one that is largely insoluble in any solvent.
• volatile organic compound refers to any compound of carbon, excluding carbon monoxide, carbon dioxide, carbonic acid, metallic carbides or carbonates, and ammonium carbonate, which participates in atmospheric photochemical reactions. Typically, volatile organic compounds have a vapor pressure equal to or greater than 0.1 mm Hg.
• volatile organic compound content (“VOC content”) means the weight of VOC per volume of the coating solids, and is reported, for example, as kilograms (kg) of VOC per liter.
• the present invention provides a method of preparing an advanced molecular weight epoxy-amine material in the presence of a reactive diluent.
• the advanced molecular weight epoxy-amine material is preferably prepared by combining an amine with an epoxy material in the presence of a reactive diluent.
• the composition which includes the advanced molecular weight epoxy-amine material and the reactive diluent, is useful for making a coating composition by making an aqueous dispersion of the composition, followed by polymerizing the reactive diluent.
• Epoxy materials suitable for use in the present invention may be prepared according to known methods including those described in U.S. Pat. Nos. 4,446,258 (Chu et al.) and 4,476,262 (Chu et al.).
• epoxy materials are prepared by reacting one equivalent of Bisphenol A or Bisphenol F with the desired number of equivalents of epichlorohydrin to produce a material with residual epoxy functionality (e.g., an epoxy resin).
• Suitable epoxy materials include, for example, those available under the trade designations EPON 828, PON 1001, EPON 1004F, EPON 1007, EPON 1009 from Resolution Performance Products (Houston, Tex.).
• epoxy materials may contain a mixture including, for example, diepoxides, monoepoxides, and aromatic polyethers that are free of epoxy groups.
• Preferred epoxy materials have an epoxy equivalent weight (EEW) of at most 2000.
• EW epoxy equivalent weight
• the epoxy material is capable of being dissolved in a reactive diluent.
• Preferred epoxy materials include glycidyl end-capped poly(Bisphenol A-co-epichlorohydrin), glycidyl end-capped poly(Bisphenol F-co-epichlorohydrin), glycidyl end-capped poly(Bisphenol F-co-epichlorohydrin)-co-(Bisphenol A-co-epichlorohydrin), poly(alkylene glycol) diglycidyl ether, poly(tetrahydrofuran) diglycidyl ether, and combinations thereof.
• the poly(alkylene glycol) diglycidyl ether is poly(ethylene glycol) diglycidyl ether or poly(propylene glycol) diglycidyl ether.
• Particularly preferred epoxy materials include, for example, those available under the trade designation EPON 1004F from Resolution Performance Products (Houston, Tex.)
• Amines useful for reacting with epoxy materials to form advanced molecular weight epoxy-amine materials include materials having primary, secondary, and/or tertiary amine-functionality.
• Useful amines include monoamines, diamines, and polyamines. Examples of useful amines include those listed in U.S. Pat. No. 4,468,307 (Wismer et al.)
• the amine has an amine equivalent weight of 22 to 300.
• Useful hydroxy-functional amines include, for example, alkanolamines, dialkanolamines, trialkanolamines, alkylalkanolamines, arylalkanolamines, arylalkylalkanolamines, and combinations thereof, in which the alkanol, alkyl, and/or aryl chains preferably contain 2 to 18 carbon atoms.
• Preferred hydroxy-functional amines include, for example, ethanolamine, N-methylethanolamine, diethanolamine, N-phenylethanolamine, N,N-dimethylethanolamine, N-methyldiethanolamine, triethanolamine, and combinations thereof.
• Non hydroxy-functional amines may also be useful. If substituted amines are used, preferably the substituents do not detrimentally affect the reaction of the amine with the epoxy material.
• Preferred non hydroxy-functional amines include, for example, ethylamine, propylamine, methylethylamine, diethylamine, N,N-dimethylcyclohexylamine, triethylamine, N-benzyldimethylamine, dimethylcocoamine, dimethyltallowamine, and combinations therof.
• amines including, for example, hydrazine and propylene imine, may also be useful.
• Ammonia may also be useful, and for the purposes of this application is considered to be an amine.
• Combinations of the various amines described above can also be used.
• Reactive diluents are used in conjunction with the epoxy materials to prepare the advanced molecular weight epoxy-amine materials and, ultimately, the coating compositions.
• “reactive diluent” refers to monomers and/or oligomers that are substantially non-reactive with the epoxy material and/or amine under the conditions used to prepare the epoxy-amine material.
• Reactive diluents useful in the present invention are preferably capable of undergoing a reaction to form a polymer and/or an interpenetrating network.
• Reactive diluents useful in the present invention include, for example, monomers and/or oligomers that are capable of undergoing free radical reactions.
• the reactive diluent has a molecular weight of 100 Daltons to 350 Daltons.
• the vinyl compound is preferably a vinyl aromatic compound.
• Useful vinyl aromatic compounds include, for example, styrene, substituted styrenes, and combinations thereof.
• the reactive diluent functions as a solvent to dissolve, disperse, or otherwise lower the viscosity of the materials used in the preparation of the epoxy-amine material.
• a reactive diluent preferably reduces or eliminates the need to use substantial amounts of a solvent, solvents may nonetheless be added as desired.
• Additional reactive diluents may be monofunctional or multifunctional reactive diluents.
• Useful additional reactive diluents in addition to the reactive diluents described above, include, for example, acrylate compounds.
• Useful acrylate compounds include, for example, butyl acrylate, ethyl acrylate, 2-ethylhexyl acrylate, isobutyl acrylate, tert-butyl acrylate, 2-hydroxyethyl acrylate, poly(ethylene glycol) acrylate, isobomyl acrylate, glycidyl acrylate, gylcidyl methacrylate, acrylic acid, and combinations thereof.
• Advanced molecular weight epoxy-amine materials may be prepared by combining an amine with an epoxy material in the presence of a reactive diluent.
• a reactive diluent Preferably, at least 0.1 equivalent of amine, more preferably at least 0.2 equivalent of amine, and most preferably at least 0.3 equivalent of amine is combined with each equivalent of epoxy material.
• at most 1.05 equivalents of amine, more preferably at most 1 equivalent of amine, and most preferably at most 0.95 equivalent of amine is combined with each equivalent of epoxy material.
• An example of a convenient procedure for preparing advanced molecular weight epoxy-amine material is to first dissolve the epoxy material in the reactive diluents.
• the epoxy material dissolves at a temperature of at most 130° C., more preferably at most 120° C., and most preferably at most 110° C.
• the materials may be agitated as desired to assist in the dissolution.
• Convenient methods of preventing the polymerization include, for example, maintaining an oxygenated condition and/or adding antioxidants and/or inhibitors.
• Preferred inhibitors include, for example, 2,6-di-tert-butyl-4-methylphenol.
• antioxidants and/or inhibitors are used, they are preferably used in at least 0.01% by weight based on based on the total combined weight of epoxy material, amine, and reactive diluent.
• antioxidants and/or inhibitors are used, they are preferably used in at most 0.5% by weight based on based on the total combined weight of epoxy material, amine, and reactive diluent.
• the temperature of the mixture may be adjusted (e.g., cooled) to the desired temperature for addition of the amine. After the addition of the amine, the temperature of the mixture may be adjusted as desired to allow the reaction to take place.
• the reaction temperature is at most 130° C., more preferably at most 120° C., and most preferably at most 110° C.
• advanced molecular weight epoxy-amine material having residual epoxy functionality may be prepared.
• the residual epoxy functionality may hydrolyze during the preparation of the aqueous dispersion to provide hydroxy functionality, which can be used, for example, to react with suitable crosslinkers.
• advanced molecular weight epoxy-amine materials having residual epoxy functionality may be reacted with active hydrogen compounds (e.g., as described below) to further advance the molecular weight of the epoxy-amine material.
• active hydrogen compounds e.g., as described below
• the reaction of an active hydrogen compound with an advanced molecular weight epoxy-amine materials having residual epoxy functionality may be carried out before making the aqueous dispersion, after making the aqueous dispersion, or after polymerizing the reactive diluent as desired.
• At most 1.05 equivalents of active hydrogen compound are used per equivalent of residual epoxy functionality.
• more preferably at most 1 equivalent of active hydrogen compound, and most preferably at most 0.95 equivalent of active hydrogen compound are used per equivalent of residual epoxy functionality.
• active hydrogen compounds and/or precursors are compounds that include at least one hydrogen atom that may be readily dissociated in an aqueous environment.
• the hydrogen atom is attached to a nitrogen atom, an oxygen atom, a phosphorous atom, or a sulfur atom.
• Useful active hydrogen compounds and/or precursors in which the active hydrogen is attached to nitrogen include, for example, amines, diamines, polyamines, hydrazides, dihydrazides, polyhydrazides, ketimines, diketimines, polyketimines, and combinations thereof.
• Useful active hydrogen compounds in which the active hydrogen is attached to oxygen include, for example, dicarboxylic acids, polycarboxylic acids, bisphenols, polyphenols, and combinations thereof.
• Useful active hydrogen compounds in which the active hydrogen is attached to sulfur include, for example, mercaptans, dimercaptans, polymercaptans, and combinations thereof.
• Preferred active hydrogen compounds include, for example, 3-mercaptopropionic acid, 2-mercaptoethanol, adipic dihydrazide, hydrazine, ammonia, ethylenediamine, N-(2-aminoethyl)ethanolamine, diethylenetriamine, triethylenetetramine, diethanolamine, bisphenol A, bisphenol F, N-ethylethylenediamine, 1,4-butanedithiol, propyleneimine, N,N′-dimethyl-1,6-hexanediamine, 1,6-hexanediamine, and combinations thereof.
• Crosslinkers may be incorporated into the coating composition to enhance the crosslinking that occurs during the cure of coating composition after being coated on a substrate and dried.
• Crosslinkers include materials that are capable of reacting with other functionalities present in the coating composition at the curing temperature.
• crosslinkers examples include amines, melamines, blocked isocyanates, glyco-uryls, ketimines, epoxies, and combinations thereof.
• Preferred crosslinkers include, for example, blocked isocyanates available under the trade designation VESTANAT 31358/100 from DeGussa Corp. (Parsippany, N.J.).
• Solvents may optionally be added to the coating compositions provided by the present invention as desired.
• a wide variety of solvents are suitable for use in the present invention. However, as previously mentioned, the use of substantial amounts of solvents may contribute to an undesirably high level of volatile organic compounds that might have to be removed or recovered.
• Useful solvents include, for example, aromatic solvents (e.g., xylene, toluene), alcohols (e.g., butanol and amyl alcohol), ethyleneglycol ethers (e.g., 2-butoxyethanol and 2-hexyloxyethanol), propyleneglycol ethers, ketones (e.g., acetone and methyl isobutyl ketone), amides (e.g., 1-methyl-2-pyrrolidinone and N,N-dimethylformamide), and combinations thereof.
• Preferred solvents include, for example, 1-methyl-2-pyrrolidinone and N,N-dimethylformamide.
• a solvent preferably at most 20% by weight, more preferably at most 10% by weight, and most preferably at most 5% by weight solvent is used, based on the total weight of the coating solids.
• the advanced molecular weight epoxy-amine material may be combined with an aqueous acid to provide an aqueous dispersion of the advanced molecular weight epoxy-amine material.
• a surfactant may be used to aid in the formation of the aqueous dispersion.
• the surfactant may be added to the advanced molecular weight epoxy-amine material either before or after the material is combined with the aqueous acid.
• the aqueous acid may include a surfactant.
• Exemplary carboxy-containing acids include, for example, lactic acid, formic acid, acetic acid, dimethylolpropionic acid, erythorbic acid, ascorbic acid, isophthalic acid, phthalic acid, terephthalic acid, maleic acid, succinic acid, propionic acid, acrylic acid, methacrylic acid, carbonic acid, oxalic acid, adipic acid, and combinations thereof.
• Exemplary phosphorous-containing acids include, for example, phosphoric acid, phosphoric acid derivatives, and combinations thereof.
• Useful persulfate inititiation systems include, for example, ammonium persulfate or other alkali metal persulfates optionally combined with a suitable reducing agent.
• suitable reducing agents include, for example, hydrazine, ammonium or alkali metal sulfites, bisulfites, metabisulfites, and hydrosulfites.
• Preferred free radical initiators include, for example, tert-butylhydroperoxide.
• Coating compositions provided by the present invention preferably have useful properties for coating substrates.
• the coating compositions provided by the present invention are preferably aqueous dispersions that are stable for at least four months at ambient conditions.
• stable coating compositions are aqueous dispersions that do not exhibit a substantial change in viscosity or exhibit colloidal instability.
• Coatings made from stable aqueous dispersion preferably have substantially the same properties as when they are made.
• Coating compositions provided by the present invention may be applied to the desired substrate by any convenient method known in the art.
• Useful methods include, for example, spraying, roller coating, dip coating, curtain coating, brushing, electro coating, and combinations thereof.
• the epoxy material prepared in Example 2 was heated to 75° C. in an oxygen atmosphere. Over a period of 90 minutes a mixture of diethanolarnine (38.91 g) and n-butylamine (14.21 g) was added. During the addition of the amine mixture the temperature was allowed to rise to 93° C. At the end of the amine addition a mixture of styrene (6.63 g) and butylmethacrylate (6.63 g) was added and the temperature was kept at 90 to 95° C. for 3 hours and 20 minutes. The temperature was adjusted to 80° C. then lactic acid (39.1 g, 85% by weight in water) was added.
• Example 2 The epoxy material prepared in Example 2 (333.62 g) was heated to 75° C. in an oxygen atmosphere. Over a period of 90 minutes a mixture of diethanolamine (38.91 g) and n-butylamine (14.21 g) was added. During the addition of the amine mixture the temperature was allowed to rise to 93° C. At the end of the amine addition a mixture of styrene (6.63 g) and butylmethacrylate (6.63 g) was added and the temperature was kept at 90 to 95° C. for 3 hours and 20 minutes.
• Coatings were prepared by casting 5 mil-wet films of Formulas 1, 2 and 3 on various substrates. The coatings were allowed to dry for 15 minutes at room temperature and were then heated to 185° C. for 30 minutes. The panels were allowed to cool to room temperature prior to any testing. TABLE 2 MEK double rub resistance. Substrate Formula 1 Formula 2 Formula 3 Bondrite B1000 100** 10 50 Bondrite B95 100 5 30 CRS Q-panel* 100 5 30 *cold rolled steel Q-panel **at 100 MEK double rubs, the rubbing was stopped.
• Substrate Formula 1 Formula 2 Formula 3 Bondrite B1000 25* 0 0 Bondrite B95 0 0 10 CRS Q-panel 0 0 0 *Adhesion test performed according to ASTM D-3359 method B, percent coating loss reported.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Health & Medical Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Medicinal Chemistry (AREA)
• Polymers & Plastics (AREA)
• Life Sciences & Earth Sciences (AREA)
• Engineering & Computer Science (AREA)
• Materials Engineering (AREA)
• Wood Science & Technology (AREA)
• Molecular Biology (AREA)
• Paints Or Removers (AREA)
• Epoxy Resins (AREA)
• Application Of Or Painting With Fluid Materials (AREA)

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• 2003
  • 2003-03-07 ES ES03713957T patent/ES2260614T3/es not_active Expired - Lifetime
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  • 2003-03-07 US US10/507,168 patent/US20050209371A1/en not_active Abandoned
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