EP0115484A4 - Compositions hydroxy-epoxydes acryliques de revetement a teneur en solides elevee. - Google Patents

Compositions hydroxy-epoxydes acryliques de revetement a teneur en solides elevee.

Info

Publication number
EP0115484A4
EP0115484A4 EP19820903089 EP82903089A EP0115484A4 EP 0115484 A4 EP0115484 A4 EP 0115484A4 EP 19820903089 EP19820903089 EP 19820903089 EP 82903089 A EP82903089 A EP 82903089A EP 0115484 A4 EP0115484 A4 EP 0115484A4
Authority
EP
European Patent Office
Prior art keywords
anhydride
coating composition
composition according
group
epoxy
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.)
Withdrawn
Application number
EP19820903089
Other languages
German (de)
English (en)
Other versions
EP0115484A1 (fr
Inventor
Mohinder S Chattha
Ares N Theodore
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.)
Ford Werke GmbH
Ford France SA
Ford Motor Co Ltd
Ford Motor Co
Original Assignee
Ford Werke GmbH
Ford France SA
Ford Motor Co Ltd
Ford Motor Co
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 Ford Werke GmbH, Ford France SA, Ford Motor Co Ltd, Ford Motor Co filed Critical Ford Werke GmbH
Publication of EP0115484A1 publication Critical patent/EP0115484A1/fr
Publication of EP0115484A4 publication Critical patent/EP0115484A4/fr
Withdrawn legal-status Critical Current

Links

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
    • 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
    • C08G59/40—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 characterised by the curing agents used
    • C08G59/42—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
    • C08G59/4215—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof cycloaliphatic
    • 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

Definitions

  • compositions both to Chattha et al.
  • This invention relates to high solids, thermosetting coating compositions, which when cured, exhibit excellent weatherability and are adapted to provide an automotive topcoat which demonstrates hardness, high gloss and excellent resistance to solvents and water.
  • the coating compositions of this invention comprise a mixture of a low molecular weight hydroxyacrylic copolymer, dicarboxylic acid anhydride including at least about 50 weight percent of an alkyl hexahydrophthatic anhydride, epoxy, and amine-aldehyde crosslinking resins.
  • the composition mixture reacts in situ during curing at elevated temperature to form the coating.
  • thermosetting coating composition of this invention preferably contains greater than about 60% by
  • composition is characterized in that it comprises a mixture of:
  • composition reacts in situ during curing at elevated temperatures to form the coating.
  • the acrylic copolymer is prepared from a monomer mixture comprising: (i) between about 10 and about 40 weight percent of monoethylenically unsaturated hydroxy alkyl esters of acrylic acid or methacrylic acid and (ii) between about 90-60 weight percent of other monoethylenically unsaturated monomers.
  • the dicarboxylic acid anhydride is included in an amount so as to provide between about 0.25 and about 1.5, preferably about 0.30 and 1.20, anhydride groups for each hydroxyl group on the acrylic copolymer.
  • the epoxy is included in an amount so as to provide at least about 1.0, preferably between about 1.1 and 1.2 epoxide groups per anhydride group.
  • the amine-aldehyde is included in the composition in amount sufficient to provide at least about 0.60, preferably between about 0.75 and 2.75, nitrogen crosslinking functional groups for each hydroxyl group initially present on the acrylic copolymer (A).
  • the coating composition of this invention may include additives such as solvents, catalysts, antioxidants, U.V. absorbers, flow control or wetting agents, antistatic agents, pigments, plasticizers, etc.
  • additives such as solvents, catalysts, antioxidants, U.V. absorbers, flow control or wetting agents, antistatic agents, pigments, plasticizers, etc.
  • NAD's non-aqueous dispersions
  • This invention overcomes the above mentioned deficiencies of prior high solids coating compositions and provides a high solids composition particularly suitable for use as an automotive topcoat, clear or pigmented, which exhibits outstanding weatherability.
  • composition of this invention is applied to the substrate : as an essentially unreacted mixture of low molecular weight materials, little or no solvent is required to maintain a desirable low application viscosity, i.e., the composition can be of very high solids level.
  • composition of this invention being of essentially single step formulation, offers a distinct commercial advantage over those compositions whose formulation includes a series of reaction steps prior to curing, since such reaction steps generally require heat, agitation and monitoring for extended periods of time.
  • carboxyl functionality is generated which, until it is later consumed by further reaction, acts as a catalyst for the crosslinking reaction.
  • the coating compositions of this invention provide a system which is particularly suitable for those applications requiring a coating having high gloss, hardness, adhesion, high solvent and water resistance and
  • OMPI superior weatherability The components of the coating composition of this invention are combined to form a homogeneous mixture which is then applied to a substrate and cured at elevated temperatures.
  • the components of the coating composition, the amounts of each of the components required to achieve the desired results of the invention and a method for applying the composition are described hereinafter in greater detail.
  • One material in the high solids coating composition of this invention is a hydroxy functional acrylic copolymer, i.e., a copolymer bearing pendant hydroxyl groups, which may be prepared by conventional free radical induced polymerization of suitable alpha-beta unsaturated monomers.
  • copolymer refers to a copolymer of two or more different monomers at least one of which contains pendant hydroxyl groups.
  • the copolymers used in the coating composition of this invention have a number average molecular weight (M n ) of between about 1000-5000, preferably between about 1500-3000.
  • the monomers used to prepare the copolymer include between about 10 and about 40 weight percent of one or more monoethylenically unsaturated monomers bearing hydroxyl functionality.
  • the monoethylenically unsaturated hydroxy functional monomers useful in preparation of the copolymer and providing the hydroxyl functionality to the copolymer may be selected from a long list of hydroxy functional monomers.
  • the hydroxy functional monomers are acrylates and may be selected from the group consisting of, but not limited to the following esters of acrylic or methacrylic acids and aliphatic alcohols: 2-hydroxyethyl acrylate; 3-chloro-2-hydroxy ⁇ ro ⁇ yl acrylate; 2-hydroxy-l-methylethyl acrylate; 2-hydroxy- propyl acrylate; 3-hydroxypropyl acrylate; 2,3 dihydroxy- propyl acrylate; 2- ydroxybutyl acrylate; 4-hydroxybutyl acrylate; diethylene glycol acrylate; 5-h roxypentyl acrylate; 6-hydroxyhexyl acrylate; triethyleneglycol acrylate; 7-hydroxyheptyl acrylate; 2 hydroxymethyl e
  • the preferred hydroxy functional monomers for use in the copolymer of the invention are C 5 - C7 hydroxy alkyl acrylates and/or Cg - Cs hydroxy alkyl methacrylates, i.e., esters of C2 - C4 dihydric alcohols and acrylic or methacrylic acids.
  • acrylate is used in this specification to include esters of both acrylic and methacrylic acid, i.e., acrylates and methacrylates.
  • the remainder of the monomers forming the copolymer i.e., between about 90 and about 60 weight percent of the monomers of the copolymer, are other monoethylenically unsaturated monomers.
  • These other monoethylenically usaturated monomers are preferably alpha-beta olefinically unsaturated monomers, i.e., monomers bearing olefinic unsaturation between the two carbon atoms in the alpha and beta positions with respect to the terminus of an aliphatic carbon-to-carbon chain.
  • alpha-beta olefinically unsaturated monomers which may be employed are other acrylates (meaning esters of either acrylic or methacrylic acids not containing hydroxyl functionality), as well as mixtures of other acrylates and monovinyl hydrocarbons.
  • acrylates meaning esters of either acrylic or methacrylic acids not containing hydroxyl functionality
  • mixtures of other acrylates and monovinyl hydrocarbons Preferably, in excess of 50 weight percent of the total of the copolymer monomers are acrylates (this total including hydroxy functional acrylates and other acrylates).
  • acrylates are preferably selected from esters of C j _ - C 2 monohydric alcohols and acrylic or methacrylic acids, i.e., methyl methacrylate, ethylacrylate, butylacrylate, ( iso)-butylmethacrylate, hexylacrylate, 2-ethylhexyl acrylate, lauryl ethacrylate, etc.
  • Monovinyl hydrocarbons when they are employed, ' should preferably constitute less than 50 weight percent of the copolymer.
  • the monovinyl hydrocarbons suitable for use in forming the copolymers are those containing 8 to 12 carbon atoms and including styrene, alpha methylstyrene, vinyl toluene, t-butylstyrene and chlorostyrene.
  • Other such monovinyl hydrocarbon monomers as vinyl chloride, acrylonitrile, methacrylonitrile, and vinyl acetate may be included in the copolymer as modifying monomers. However, when employed, these modifying monomers should constitute only between about 0 and about 30 weight percent of the monomers in the copolymer.
  • Small amounts of ethylencally unsaturated carboxylic acids can also be used in preparing the copolymer, such as acrylic acid, methacrylic acid, crontonic acid, itaconic acid, aleic acid and the like.
  • a preferred embodiment of this invention comprises a copolymer of 2-hydroxyethyl acrylate, methyl methacrylate, isobutyl methacrylate and styrene.
  • the hydroxy functional monomers and the other monoethylenically unsaturated monomers are mixed and reacted by conventional free radical initiated polymerization in such proportions as to obtain the copolymer desired.
  • free radical initiators are known to the art and are suitable for the purpose.
  • the suitable solvents are toluene, methyl amyl ketone, xylene, dioxane, butanone, etc. If the hydroxy- functional copolymer is prepared in solution, the solid copolymer can be precipitated by pouring the solution at .a slow rate into a nonsolvent for the copolymer such as hexane, octane, or water under suitable agitation conditions.
  • a nonsolvent for the copolymer such as hexane, octane, or water under suitable agitation conditions.
  • copolymer useful in the compositions of this invention can also be prepared by emulsion polymerization, suspension polymerization, bulk polymerization, or combinations thereof, or still other suitable methods.
  • chain transfer agents may be required to control molecular weight of the copolymer to a desired range. When chain transfer agents are used, care must be taken so they do not decrease the shelf stability of the composition by causing premature chemical reactions.
  • the anhydride used in this composition comprises at least about 50 percent by weight, and up to 100 percent by weight, of alkyl hexahydrophthalic anhydride,
  • the alkyl group preferably comprises up to about 7 carbons, more preferably up to 4 carbons.
  • the alkyl hexahydrophthalic anhydride comprises methyl hexahydrophthalic anhydride.
  • the remainder of the anhydrides i.e., 0 to about 50 weight percent, more preferably 0 to about 20 weight percent, and most preferably 0 to about 10 percent by weight, are selected from a variety of anhydrides, which include but are not limited to, hexahydrophthalic, 2-dodecene-l-ylsuccinic, tetrahydrophthalic, methyl tetrahydrophthalic and camphoric anhydrides, and mixtures of suitable anhydrides.
  • the anhydride is included in the composition in an amount sufficient to provide between about 0.25 and about 1.2, more preferably between about 0.30, and about 1.2 most preferably between about 0.5 and 1.1 anhydride groups for each hydroxyl group initially present on the copolymer.
  • the anhydride reacts with hydroxyl groups on the copolymer forming carboxyl groups.
  • excess anhydride i.e., relative hydroxyl groups
  • the excess anhydride will later react with the hydroxyl groups generated by previous carboxyl/epoxide reactions to form more carboxyl groups. Since the epoxide is present in an amount substantially corresponding to the anhydride, these carboxyl groups will subsequently be reacted with epoxide to form (i.e., regenerate) hydroxyl functionality.
  • This composition also includes an epoxy having one or more epoxide groups per molecule and having a number average molecular weight (M n ) between about 130 and about 1500.
  • the epoxy used in the invention composition is a diepoxide. It is believed that, during curing, the carboxyl group opens the epoxide ring of the epoxy in an esterification reaction which generates hydroxyl groups.
  • the epoxy is present in the composition in an amount sufficient to provide at least about 1.0 more preferably between about 1.0 and 1.2, most preferably between about 1.0 and 1.1 epoxide groups for each anhydride group present in the composition, i.e., essentially all of the pendant carboxyl groups resulting from the initial hydroxy copolymer anhydride reaction and, in the case of excess anhydride, the carboxyl groups resulting from subsequent hydroxyl-excess anhydride reactions will be reacted with an epoxide to regenerate hydroxyl functionality.
  • the epoxy suitable for use in this invention is a low molecular weight epoxy which can : be a liquid or a solid and can be either a single epoxy or a mixture of suitable epoxies.
  • suitable epoxies include, but are not limited to, C4 _ Cig monoepoxies such as alkylene oxides, cyclic oxides, glycidyl esters and glycidyl ethers. Amoung numerous examples of such monoepoxides are 1,2 epoxy pentane, 1,2-epoxy decane, styrene oxide, cyclohexene oxide, n-butyl glycidyl ether, glycidyl acetate and glycidol.
  • Suitable diepoxides include those which are the condensation products of bisphenol-A with epichlorohydrin, examples of which are commercially available as Epon 828, 1001, 1004, 1007 and 1009 (marketed by Shell Chemical Company, Houston, Texas), Araldite 6010 and 8001 (marketed by Ciba-Geigy Corp., Ardsley, New York); ester type diepoxides such as diglycidyl phthalate, diglycidyl adipate and diglycidyl glutarate; cycloaliphatic diepoxides such as dicycopentaxediene and vinyl _ cyclohexane dioxide; and aliphatic ether type diepoxides such as ethylene glycol diglycidyl ether, 1,2-propylene glycol, diglycidyl ether and 1,4-butanediol diglycidyl ether such as Araldite RD-2 (marketed by Ciba-Geigy).
  • Epoxies having more than two epoxide groups per molecule such as triepoxy resins XB2818 (Ciba-Geigy) and Dion 711 (Diamond Shamrock Chemical Co., Morristown, N.J.) and tetraepoxy resin 0163 (Ciba-Geigy) may also be used.
  • the epoxies may be substituted by non-interferring functionality such as hydroxyl or the carbon chain may be interrupted by oxygen, and may contain ethylenic unsaturation; however a saturated epoxy and one containing no hydroxyl functionality is preferable. It is also preferred that the epoxy of this composition contain terminal epoxide groups.
  • Catalysts are generally included in the composition to accelerate the epoxide/carboxyl reaction.
  • Suitable catalyst for this epoxide/carboxyl reaction are well known in the art.
  • Preferred catalysts useful for this reaction are the tetralkyl ammonium salts such as tetra methyl ammonium chloride, tetraethyl ammonium bromide and trimethyl benzyl ammonium chloride as well as metal salts of a carboxylic acid, such as potassium octoate or chromium III octoate.
  • catalysts include: metal halides such as chromium trichloride, ferric trichloride, and aluminum trichloride; mercaptans and thioethers such as octyl mercaptan, dimercapto propanol and dimercapto-diethyl ether; * tertiary amines such as triethyl amine, pyridine, dimethylandine, quinoline, ⁇ -picoline, ethylpyridine, and the like. Still other catalysts known to catalyze the carboxyl/epoxide reaction will be apparent to those skilled in this art.
  • amine-aldehyde crosslinking agent Another essential component of the paint compositions of this invention is an amine-aldehyde crosslinking agent.
  • Amine-aldehyde crosslinking agents suitable for crosslinking hydroxy functional bearing materials are well known in the art. Typically, these crosslinking materials are products of reactions of melamine, or urea with formaldehyde and various alcohols containing up to and including 4 carbon atoms.
  • the amine-aldehyde crosslinking agents useful in this invention are amine-aldehyde resins such as condensation products of formaldehyde with melamine, substituted melamine, urea, benzoquanamine or substituted benzoquanamine.
  • Preferred members of this class are methylated melamine-formalade yde resins such as hexamethoxylmelamine.
  • These liquid crosslinking agents have substantially 100 percent nonvolatile content as measured by the foil method at 45°C for 45 minutes.
  • Other suitable amine-aldehyde crosslinking agents would be apparent to one skilled in the art.
  • crosslinking agents are t e amino crosslinking agents sold by American Cyanamid, Wayne, N.J. under the trademark "Cymel” .
  • Cymel 301, Cymel 303, Cymel 325 and Cymel 1156 which are alkylated melamine-formaldehyde resins, are useful in the compositions of this invention.
  • the crosslinking reactions are known to be catalytically accelerated by acids. Therefore, the unconsumed carboxyl group acts as a catalyst for the crosslinking reaction.
  • catalysts may be added to the composition which accelerate the crosslinking reaction.
  • One such catalyst for example, is p-toluene sulfonic acid and the amine salts thereof.
  • the amine-aldehyde materials function as a crosslinking agent in the composition of the invention by reacting with the hydroxyl groups of the composition, which groups were either present initially on the copolymer and nonreacted or regenerated during subsequent in situ reactions of intially present hydroxyl groups.
  • the amount of amino crosslinking agent be sufficient to substantially crosslink the hydroxyl groups in the coating composition.
  • the amino crosslinking agent should be included in the composition in an amount sufficient to provide at least about 0.60 preferably between about 0.75 and about 2.75 of nitrogen crosslinking functional groups for each hydroxyl group included in the composition either as an initially present and unreacted hydroxyl group on the copolymer or as a regenerated hydroxyl group i.e., by means of in situ reactions with anhydride and epoxy.
  • the hydroxyl groups present in the composition and available for crosslinking can therefore be essentially taken to be equal to the hydroxyl groups initially present on the copolymer (A).
  • coating compositions of the invention include materials such as catalysts, antioxidants, U.V. absorbers, solvents, surface modifiers and wetting agents, as well as pigments.
  • suitable solvents which may be employed include those commonly used, such as toluene, xylene, methyl amyl ketone, acetone, butyl acetate, tetrahyd ofuran, ethylacetate, di ethylsuccinate, di ' methylglutarate, dimethyladipate or mixtures thereof.
  • solvent in which the hydroxy acrylic copolymer is prepared, may be employed as a solvent for the coating composition thus eliminating the need for, drying the copolymer after preparation, if such is desired. Typical solvents which may be so used are detailed above.
  • the nonvolatile solids content of the coating composition is preferably at least 60% and more preferably 70% or more, thus limiting the amount of solvent included in the composition.
  • the composition is particularly suitable for use as a high solids composition, the composition is also suitable for use as low solids compositions. Determination of optimal solids content for a given application would be within the skill of one in the art.
  • Surface modifiers or wetting agents are comomon additives for liquid paint compositions. The exact mode of operation of these surface modifiers is not known, but it is thought that their presence contributes to better adhesion of the coating composition to the surface being coated and helps formation of thin coatings, particularly on metal surfaces.
  • These surface modifiers are exemplified by acrylic polymers containing 0.1 - 10 percent by weight of copolymerized monoethylenically unsaturated carboxylic acids such as methacrylic acid, acrylic acid or itaconic acid, cellulose acetate butyrate, silicone oils or mixtures thereof.
  • the choice of surface modifiers or wetting agent is dependent upon the type of surface to be coated and selection of the same is clearly within the skill of the artisan.
  • the coating composition of the invention also may include pigments.
  • the amount of pigment in the coating composition may vary, but preferably is between about 3 and about 45 weight percent based on the total weight of the paint composition. If the pigment is metallic flake, the amount generally ranges from about 1 to about 20 weight percent.
  • NAD's such as described by Porter (S. Porter, Jr. and B.N. McBane, U.S. Patent 4,025,474, May 24, 1977) are compatible with these coating compositions. These particle dispersions may be included in an amount up to 15% by weight of the total composition.
  • Other types of NAD's such as described by D.L. Maker and S.C. Peng (U.S. Patent 3,814,721, June 4, 1974) or by S.K. Horvath (U.S. application Serial No. 292,853, filed August 14, 1981) also may be included in the paint composition.
  • the coating composition can be applied by conventional methods known to those skilled in the art. These methods include roller coating, spray coating, dipping or brushing and, of course, the particular application technique chosen will depend on the particular substrate to be coated and the environment in which the coating operation is to take place.
  • a particularly preferred technique for applying the high solids coating compositions is spray coating through the nozzle of a spray gun.
  • High solids paints have in the past caused some difficulty in spray coating techniques because of the high viscosity of the materials and resultant problems in clogging of spray guns.
  • the compositions of this invention demonstrate relatively low viscosity, considering the high solids content, they can be applied by spray coating techniques.
  • a hydroxy acrylic copolymer is prepared from the following monomers:
  • Methyl methacrylate 160 40 Styrene 20 5
  • the reulting mixture is stirred for one minute and then spray applied to primed panels in three coats with an intermediate flash of one minute and a final flash of five minutes.
  • the panels are baked at 135° C for 20 minutes to obtain clear coatings with excellent hardness, adhesion, gloss and solvent (methyl ethyl ketone and xylene) resistance.
  • a hydroxy acrylic copolymer is prepared from the following monomers:
  • An acrylic copolymer is prepared from the following monomers:
  • butyl methacrylate 26 Ethylhexyl acrylate 20 Hydroxyethyl acrylate 30 Styrene 24
  • the preparation is carried out in the same way as outlined in Example 1 by using cellusolve acetate as the solvent and tert-butyl peroctoate (5% of monomers) as initiator to obtain a 70% solution of the polymer.
  • Example 7 Fifty-two (52) parts of the above mill base are mixed with 20 parts of polymer from Example 4, 13.5 parts of ⁇ pon 828 (Shell Chemical Co.), 19 parts of Cymel 325, 0.15 parts of Cordova Accelerator AMCTM-2 and 16 parts of butyl acetate. Twelve (12) parts of methylhexa ⁇ hydrophthalic anhydride are added to the above mixture and the resulting formulation is applied by spraying to primed steel panels which are baked at 130°C for 18 minutes to obtain hard, glossly yellow coatings with excellent solvent resistance.
  • Example 7 Twelve (12) parts of methylhexa ⁇ hydrophthalic anhydride are added to the above mixture and the resulting formulation is applied by spraying to primed steel panels which are baked at 130°C for 18 minutes to obtain hard, glossly yellow coatings with excellent solvent resistance.
  • phthalo blue pigment Five (5) parts of phthalo blue pigment are mixed with 45 parts of the polymer from Example 1 and the mill base is ground as described in Example 5.
  • Example 9 Twenty-four (24) parts of the above mill base are mixed with 32 parts of the polymer from Example 1, 27 parts of Cymel 325, 14 parts of Epon 828 (Shell Chemical Co.), 8 parts flow control additive (prepared according to U.S. Patent 4,025,474), 0.1 part Cordova Accelerator AMCTM-2, 5 parts of aluminum flakes and 18 parts of butyl acetate. Twelve (12) parts of methylhexahydrophthalic anhydride are added to the above mixture and the resulting formulation is applied by spraying in four coats. The panels are baked at 130°C for , 18 minutes to obtain blud metallic coatings with excellent physical properties.
  • Example 9 Twenty-four (24) parts of the above mill base are mixed with 32 parts of the polymer from Example 1, 27 parts of Cymel 325, 14 parts of Epon 828 (Shell Chemical Co.), 8 parts flow control additive (prepared according to U.S. Patent 4,025,474), 0.1 part Cordova Accelerator AMCTM-2, 5 parts of aluminum flakes and 18 parts of but
  • a hydroxy acrylic copolymer is prepared from the following monomers:
  • this invention has industrial applicability, particularly to the automotive industry, and provide a coating with excellent exterior weatherability and distinct commercial advantages.

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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)
  • Paints Or Removers (AREA)

Abstract

Composition de revêtement thermodurcissable avec une excellente adaptation aux conditions météorologiques, adaptée pour être utilisée comme couche ou revêtement supérieur d'automobile et qui, après polymérisation, forme un revêtement résistant, vitreux, dur. La composition de revêtement, qui réagit in situ pendant la polymérisation, a pour caractéristique d'être composée d'un mélange: (A) de copolymère acrylique portant des groupes hydroxyles pendants et dont le poids moléculaire numérique moyen (Mn) varie entre approximativement 1000 et 5000, (B) d'anhydride d'acide dicarboxylique comprenant au moins 50 % en poid d'anhydride alcoyle hexahydrophtalique, (C) d'époxy portant un groupe époxyde ou plus par molécule et dont le poids moléculaire (Mn) varie entre approximativement 130 et 1500, et (D) d'agent amino-aldéhyde de liaison transversale.
EP19820903089 1982-08-09 1982-08-09 Compositions hydroxy-epoxydes acryliques de revetement a teneur en solides elevee. Withdrawn EP0115484A4 (fr)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/US1982/001091 WO1984000771A1 (fr) 1982-08-09 1982-08-09 Compositions hydroxy-epoxydes acryliques de revetement a teneur en solides elevee

Publications (2)

Publication Number Publication Date
EP0115484A1 EP0115484A1 (fr) 1984-08-15
EP0115484A4 true EP0115484A4 (fr) 1985-04-11

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US4650718A (en) * 1985-08-19 1987-03-17 Ppg Industries, Inc. Color plus clear coatings employing polyepoxides and polyacid curing agents
CA1326582C (fr) * 1986-08-21 1994-01-25 Ronald Ruthvoyne Ambrose Composition de revetement thermodurcissable a haut extrait sec pour epoxy, polyols et anhydrides
US4755582A (en) * 1986-08-21 1988-07-05 Ppg Industries, Inc. Thermosetting high solids coating composition of hydroxy-functional epoxies and anhydrides
US4732791A (en) * 1986-08-21 1988-03-22 Ppg Industries, Inc. Color plus clear application of thermosetting high solids coating composition of epoxies, polyols and anhydrides
US4917955A (en) * 1987-07-13 1990-04-17 Ppg Industries, Inc. Color plus clear composite coating having a catalyst-free base coat comprising polyepoxides and polyacid curing agents
US4849283A (en) * 1987-07-16 1989-07-18 Ppg Industries, Inc. Composite coatings employing polyepoxides and polyacid curing agents in base coats
US5411809A (en) * 1987-11-16 1995-05-02 The Sherwin-Williams Company Reactive coatings comprising an acid-functional compound, an anhydride-functional compound and an epoxy-functional compound
US5043220A (en) * 1987-11-16 1991-08-27 The Sherwin-Williams Company Substrate coated with a basecoat and/or a clearcoat of an acid-functional compound, an anhydride-functional compound, an epoxy-functional compound and a hydroxy-functional compound
US4946744A (en) * 1987-11-16 1990-08-07 The Sherwin-Williams Company Substrate coated with a clearcoat/basecoat composition comprising an anhydride-functional compound and an hydroxy-functional compound
US4871806A (en) * 1987-11-16 1989-10-03 The Sherwin-Williams Company Reactive coatings comprising an acid-functional compound, an anhydride-functional compound, an epoxy-functional compound and a hydroxy-functional compound
DE4027609A1 (de) * 1990-08-31 1992-03-05 Bayer Ag Bindemittelkombinationen und ihre verwendung in beschichtungsmitteln und dichtmassen
DE4027742A1 (de) * 1990-09-01 1992-03-05 Bayer Ag Bindemittelkombinationen und ihre verwendung in beschichtungsmitteln und dichtmassen
DE4416282A1 (de) * 1994-05-07 1995-11-09 Herberts Gmbh Bindemittelzusammensetzung, diese enthaltende Überzugsmittel, deren Herstellung und Verwendung
DE19652144C1 (de) * 1996-12-14 1998-01-22 Herberts Gmbh Überzugsmittel und Verfahren zur Herstellung von Mehrschichtlackierungen
DE19652145A1 (de) * 1996-12-14 1998-06-18 Herberts Gmbh Bindemittelzusammensetzung, diese enthaltende Überzugsmittel, deren Herstellung und Verwendung
US6037014A (en) * 1997-11-06 2000-03-14 The Edgington Co. Coating composition

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EP0092624A2 (fr) * 1981-12-28 1983-11-02 E.I. Du Pont De Nemours And Company Composition de revêtement et précurseur copolymère hydroxy-acrylique pour sa préparation

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EP0115484A1 (fr) 1984-08-15

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