WO1995028448A1 - Procede de preparation de compositions de revetement liquides - Google Patents

Procede de preparation de compositions de revetement liquides Download PDF

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Publication number
WO1995028448A1
WO1995028448A1 PCT/US1995/004320 US9504320W WO9528448A1 WO 1995028448 A1 WO1995028448 A1 WO 1995028448A1 US 9504320 W US9504320 W US 9504320W WO 9528448 A1 WO9528448 A1 WO 9528448A1
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WIPO (PCT)
Prior art keywords
solid particles
cross
particle size
curable resin
epoxy
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PCT/US1995/004320
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English (en)
Inventor
Yeong-Ho Chang
Joseph Clark Jernigan
Lanney Calvin Treece
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Eastman Chemical Company
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Publication of WO1995028448A1 publication Critical patent/WO1995028448A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
    • C08J3/03—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/02—Emulsion paints including aerosols

Definitions

  • the invention relates to liquid coating composi— tions, and more particularly to a method for preparing aqueous coating compositions containing curable resins and cross—linking agents that are reactive with the resins.
  • Plastic materials used in the manufacture of powder coatings are classified broadly as either thermosetting or thermoplastic.
  • heat is applied to the coating on the substrate to melt the particles of the powder coating and thereby permit the particles to flow together and form a smooth coating.
  • thermosetting coatings when compared to coatings derived from thermoplastic compositions, generally are tougher, more resistant to solvents and detergents, have better adhesion to metal substrates, and do not soften when exposed to elevated temperatures.
  • the curing of thermosetting coatings has created problems in obtaining coatings which have, in addition to the above stated desirable characteristics, good smoothness and flexibility.
  • Coatings prepared from thermosetting powder compositions upon the application of heat, may cure or set prior to forming a smooth coating, resulting in a relatively rough finish referred to as an "orange peel" surface. Such a coating surface or finish lacks the gloss and luster of coatings typically obtained from thermoplastic compositions.
  • thermosetting coatings have caused thermosetting coatings to be applied from organic solvent systems, as disclosed, for example, in GB 1,572,996.
  • the use of such solvent systems is inherently undesirable not only because of the expense of the solvents but also because of the environmental and safety problems that may be occasioned by their evaporation.
  • thermosetting coating compositions In addition to exhibiting good gloss, impact strength, and resistance to solvents and chemicals, coatings derived from thermosetting coating compositions must possess good to excellent flexibility. For example, good flexibility is essential for powder coating compositions used to coat sheet steel that is destined to be formed or shaped into articles used in the manufacture of various household appliances and automobiles, in the course of which the sheet metal is flexed or bent at various angles.
  • Formation of a powder coating composition typically entails the dry mixing of flakes or granules of resin with the cross—linking agent and other ingredients, extruding the mixture at temperatures in the range of about 80° to 130°C, cooling the extrudate, and then chipping and grinding the resulting solid into particles of suitable size.
  • This pulverizing operation typically produces a powder in which the particles are characterized by irregular shape and a broad size distribution.
  • U.S. Patent No. 3,759,864 discloses a process for preparing pigmented epoxy resin particles by emulsifying the liquified polymer in a continuous volatile liquid phase containing pigment at temperatures in the range of 80—150°C, cooling the mixture to solidify the polymer, and removing the volatile liquid.
  • U.S. Patent No. 3,759,864 discloses a process for preparing pigmented epoxy resin particles by emulsifying the liquified polymer in a continuous volatile liquid phase containing pigment at temperatures in the range of 80—150°C, cooling the mixture to solidify the polymer, and removing the volatile liquid.
  • particles of a polyhydroxy polyether resin are prepared by mixing the.resin with water containing a polymeric polycarboxylic acid or salt at a temperature of at least 60°C, agitating the mixture to form a dispersion, and cooling to form solid polymer particles.
  • the resin, cross—linking agent, and other ingredients may be dissolved in a water miscible organic solvent such as a glycol ether (Cellosolve ® , for example) ; the resulting solution can be added to water with vigorous agitation to produce powder coating particles, which can be separated from the liquid phase and dried.
  • a water miscible organic solvent such as a glycol ether (Cellosolve ® , for example)
  • Methods of forming powder coating compositions that utilize standard pulverization processes following extrusion subject the compositions to high temperature and produce dusty powders with broad particle size distribution.
  • the use of organic solvents to accomplish mixing of the components of the composition is undesirable from the standpoint both of cost and environmental consequences.
  • the method of the present invention avoids the use of high temperatures that are typically used in extrusion mixing and can lead to premature curing of the resin; it also avoids the use of organic solvents for dissolution of the resin and cross- linking agents.
  • the present invention provides a method for preparing a liquid coating composition which comprises; (a) forming a mixture comprising a suspension of coarse solid particles which include a curable resin and a cross—linking agent that is reactive with the curable resin, the coarse solid particles having a mean particle size of about 30 ⁇ m to 500 ⁇ m, in an aqueous liquid medium comprising water and a surfactant; and
  • compositions prepared by the method of the invention which avoids the use of high temperatures and organic solvents, can be conveniently applied to substrates by spraying, with subsequent drying and curing of the coating at relatively low temperatures.
  • the method of the present invention provides an aqueous coating composition that comprises fine solid particles which include a curable resin and a cross- linking agent reactive with the curable resin and are suspended in an aqueous liquid medium comprising water and a surfactant.
  • the curable resin is preferably chosen from resins used in the powder coating art which have epoxy, carboxy, hydroxy, amino, or anhydride functional groups that can react with cross—linking compounds to provide cured coatings.
  • Preferred epoxy functional resins generally have a molecular weight of about 300 to about 4000, and have approximately 0.05 to about 0.99 epoxy groups per 100 grams of resin, i.e., 100—2000 weight per epoxy (WPE) .
  • WPE weight per epoxy
  • Such resins are widely known and include those that are commercially available under the EP0NTM tradename of the Shell Chemical Company, the AralditeTM tradename of CIBA— Geigy, and D.E.R. resins of the Dow Chemical Company.
  • Curable resins which have carboxy functional groups include polyesters. Such polyesters preferably have a molecular weight of about 500 to about 5000 and an acid number of about 35—75.
  • Commercially available examples of such resins include AlftalatTM AN 720, 721, 722, 744, 758 and AlftalatTM AN 9970 and 9983 resins available from Hoechst Celanese.
  • Curable resins which have free hydroxy groups also include the polyesters as well as acrylic polymers. Hydroxy—functional polyesters and acrylic polymers preferably have a hydroxyl number from about 30 to about 60 (mg KOH/g polymer) .
  • the polyesters as described herein may be produced using well—known polycondensation procedures employing an excess of glycol (or acid) to obtain a polymer having the specified hydroxyl (or carboxy1) number.
  • the glycol residues of the polyester component may be derived from a wide variety and number of aliphatic, alicyclic, and aralkyl glycols or diols containing from 2 to about 10 • carbon atoms.
  • glycols examples include ethylene glycol, propylene glycol, 1, 3—propanediol, 2,4— dimethyl—2—ethylhexane-1,3-diol, 2,2-dimethyl-l,3— propanediol, 2—ethyl—2—butyl—1,3-propanediol, 2—ethy1-2- isobutyl—1,3—propanediol, 1,3—butanediol, 1,4—butane- diol, 1,5— entanediol, 1,6—hexanediol, thiodiethanol, 1,2—, 1,3— and 1,4—cyclohexanedimethanol, 2,2,4,4— tetramethyl—1,3—cyclobutanediol, 1,4—xylylenediol, and the like.
  • the dicarboxylic acid constituent of the polyesters may be derived from various aliphatic, alicyclic, aliphatic—alicyclic, and aromatic dicarboxylic acids containing about 4 to 10 carbon atoms or ester—forming derivatives thereof, such as dialkyl esters and/or anhydrides.
  • Succinic, glutaric, adipic, azelaic, sebacic, fumaric, maleic, itaconic, 1,3— and 1,4— cyclohexanedicarboxylie, phthalic, isophthalic and terephthalic are representative of the dicarboxylic acids from which the diacid residues of the amorphous polyester may be derived.
  • a minor amount, e.g., up to 10 mole percent, of the glycol and/or diacid residues may be replaced with branching agents, e.g., tri— functional residues derived from trimethylolethane, trimethylolpropane and trimellitic anhydride.
  • branching agents e.g., tri— functional residues derived from trimethylolethane, trimethylolpropane and trimellitic anhydride.
  • the preferred polyesters suitable for the practice of this invention have a glass transition temperature, T g , greater than 55°C, and an inherent viscosity of about 0.15 to 0.4 dL/g determined using 0.5 g/lOOmL of a 60/40 (w/w) phenol/tetrachloroethane blend at 25°C.
  • the polyester resin preferably comprises (1) diacid residues of which at least 50 mole percent are terephthalic or isophthalic acid residues, (2) glycol residues of which at least 50 mole percent are derived from 2,2— imethyl— 1,3—propanediol (neopentyl glycol) and (3) up to 10 mole percent, based on the total moles of (2) and (3) , of trimethylolpropane residues.
  • These preferred hydroxyl functional polyesters are commercially available, e.g., under the names RucoteTM 107 and Cargill Resin 3000, and/or can be prepared according to the procedures described in U.S. Patent. Nos.
  • the most preferred polyester consists essentially of terephthalic acid residues, 2,2—dimethyl—1,3—propanediol residues and up to 10 mole percent, based on the total moles of 2,2—dimethyl—1,3—propanediol residues, of trimethylolpropane residues, and possesses a glass transition temperature, T , of about 50° to 65°C, a hydroxyl number of about 35 to 60, an acid number of less than 10, and an inherent viscosity of about 0.1 to 0.25.
  • a curable acrylic resin suitable for the practice of this invention is preferably a polymer or resin prepared by polymerization of a hydroxy—substituted monomer such as hydroxyethyl methacrylate, hydroxyethyl aerylate, hydroxyhexyl aerylate, hydroxyhexyl meth— acrylate, hydroxypropyl aerylate, hydroxypropyl methacrylate, hydroxybutyl acrylate, hydroxylbutyl methacrylate, and the like, optionally polymerized with other monomers such as methyl acrylate, methyl meth— acrylate, ethyl acrylate, ethyl methacrylate, butyl acrylate, butyl methacrylate, isobutyl acrylate, isobutyl methacrylate, eth lhexyl acrylate, ethylhexyl methacrylate, styrene, vinyl acetate, and the like.
  • the ratio of reagents and molecular weights of the resulting acrylic polymers are preferably chosen so as to give polymers with an average functionality (the number of OH groups per molecule) greater than or equal to 2.
  • curable hydroxy—functional acrylic polymers include JoncrylTM 800, JoncrylTM 500, and NeocrylTM LE 800.
  • Curable resins containing epoxy groups which are suitable for the practice of the present invention can also be resins comprised of residues of glycidyl methacrylate (GMA) and/or glycidyl acrylate. Such resins generally have a number average molecular weight of about 500 to about 5000 and a weight average molecular weight of about 1000 to about 10,000.
  • the resin is a glycidyl meth ⁇ acrylate resin containing from about 5 to about 40 weight percent GMA residues, having a number average molecular weight of about 1000 to about 3000 and a weight average molecular weight of about 2000 to about 8000.
  • Commercially available resins include those available from Mitsui Toatsu Chemicals, Inc., available under the tradename AlmatexTM PD 6100, PD 6300, PD 7110, PD 7210, PD 7310, PD 7610, and PD 1700. Further examples of such resins include those described in U.S. Patent Nos. 4,042,645; 4,091,024; 4,346,144; and 4,499,239, the disclosures of which are incorporated herein by reference.
  • cross—linking agents suitable for use in the present invention are well known in the art of powder coatings.
  • carboxy functional resins cross—linking compounds with epoxy groups can be utilized.
  • an epoxy functional resin an anhydride type cross—linking compound can be used.
  • hydroxy—functional resins blocked isocyanates can be used.
  • a carboxy functional resin may be blended with an epoxy resin, optionally in the presence of another epoxy functional compound such as triglycidyl isocyanurate, and cured.
  • anhydride type cross—liking compounds examples include trimellitic anhydride, benzophenone tetra— carboxylic dianhydride, pyro ellitic dianhydride, tetrahydrophthalic anhydride, and the like.
  • carboxy—functional cross—linking agents are C 3 —C 30 alkyl, alkenyl, or alkynyl compounds with two or more carboxylic acid functional groups.
  • Preferred carboxy—functional cross—linking compounds can be described by the formula
  • n is an integer from 1—10.
  • carboxy—functional cross—linking agents include compounds such as dodecanedioic acid, azelaic acid, adipic acid, 1,6—hexanedioic acid, succinic acid, pimelic acid, sebacic acid, and the like.
  • carboxy—type cross—linking compounds include maleic acid, citric acid, itaconic acid, aconitic acid, and the like.
  • the blocked polyisocyanate compounds suitable for the practice of this invention are known compounds and may be obtained from commercial sources or prepared according to published procedures. Upon being heated to cure coatings of the compositions, the compounds become unblocked and the isocyanate groups react with hydroxy groups present in the polymer to cross—link the polymer chain ⁇ and thus cure the compositions to form tough coatings.
  • Examples of blocked polyisocyanate cross- linking agents include those which are based on isophorone diisocyanate blocked with e—caprolactam, commercially available as H ⁇ ls 1530 and Cargill 2400, or toluene 2,4—diisocyanate blocked with e—caprolactam, commercially—available as Cargill 2450, and phenol- blocked polyisocyanate.
  • blocked polyisocyanate cross—linking agents or compounds are those commonly referred to as e—caprolactam—blocked isophorone diisocyanate, e.g. , those described in U.S. Patent Nos. 3,822,240, 4,150,211 and 4,212,962, the disclosures of which are incorporated herein by reference.
  • the products marketed as e—caprolactam blocked isophorone diisocyanate may consist primarily of the blocked, difunctional, monomeric isophorone diiso ⁇ cyanate, i.e., a mixture of the cis and trans isomers of 3—isocyanatomethyl—3,5,5—trimethyleyclohexylisocyanate, the blocked, difunctional dimer thereof, the blocked, trifunctional trimer thereof or a mixture of the monomeric, dimeric and/or trimeric forms.
  • the blocked polyisocyanate compound used as the cross- linking agent may be a mixture consisting primarily of the e—caprolactam—blocked, difunctional monomeric isophorone diisocyanate and the e—caprolactam blocked, trifunctional trimer of isophorone diisocyanate.
  • the description herein of the cross—linking agents as "polyisocyanates" refers to compounds which contain at least two isocyanate groups that are blocked with, i.e., reacted with, another compound, e.g., e—caprolactam.
  • the reaction of the isocyanato groups with the blocking compound is reversible at elevated temperatures, e.g., normally about 150°C, and above, at which temperature the isocyanato groups are available to react with the hydroxyl groups present in the polymer to form urethane linkages.
  • the blocked isocyanate may be a cross—linking effective amount of an adduct of the 1,3— diazetidine—2,4—dione dimer of isophorone diisocyanate and a diol having the structure
  • R 1 is a methylene—1,3,3—trimethy1—5—cyclohexyl diradical
  • R 2 is a divalent aliphatic, cycloaliphatic, aralkyl or aromatic residue of a diol
  • X is a 1,3— diazetidine—2,4—dionediyl radical, wherein the ratio of NCO to OH groups in the formation of the adduct is about 1:0.5 to 1:0.9, the mole ratio of diazetidinedione to diol is from 2:1 to 6:5, the content of free isocyanate groups in the adduct is riot greater than 8 weight percent, and the adduct has a molecular weight of about 500 to 4000 and a melting point of about 70° to 130°C.
  • the adducts of the 1, 3—diazetidine—2,4—dione dimer of isophorone diisocyanate and a diol are prepared according to the procedures described in U.S. Patent No. 4,413,079, the disclosures of which are incorporated herein by reference, by reacting the diazetidine dimer of isophorone diisocyanate, preferably free of iso— cyanurate trimers of isophorone diisocyanate, with diols in a ratio of reactants which gives as isocyanato:hydroxyl ratio of about 1:0.5 to 1:0.9, preferably 1:0.6 to 1:0.8.
  • the adduct preferably has a molecular weight of 1450 to 2800 and a melting point of about 850 to 120°C.
  • the preferred diol reactant is 1,4— butanediol.
  • Such an adduct is commercially available under the name H ⁇ ls BF1540.
  • the amount of the blocked diisocyanate cross- linking agent present in tn compositions prepared by the method of this invention can be varied to control the properties of the resulting coatings.
  • the amount of cross—linking agent which will effectively cross—link the curable resin to produce coatings having a desirable combination of properties is in the range of about 5 to 30 weight percent, preferably 15 to 25 weight percent, based on the total weight of cross—linking agent and resin.
  • a catalyst such as dibutyltin dilaurate (DBTDL) may be used to facilitate cross—linking by the polyisocyanate compound. Based on the weight of cross—linking agent, 0.5 to 5 weight percent, preferably 1 to 2 weight percent, of the catalyst may be employed.
  • the liquid coating compositions produced by the method of this invention may be prepared from the compositions described herein by first mixing, in the dry state or in an aqueous suspension, the curable resin and the cross—linking agent along with other additives commonly used in powder coating compositions.
  • Typical of the additives which may be present in these compositions are benzoin, flow aids or flow control agents, stabilizers, pigments, and dyes.
  • the coating compositions prepared by the method of the invention preferably contain flow aids, also referred to as flow control or leveling agents, to enhance the surface appearance of cured coatings of the liquid coating compositions.
  • Such flow aids typically comprise acrylic polymers and are available from several suppliers, e.g. , ModaflowTM from Monsanto Company and AcronalTM from BASF.
  • flow control agents which may be used include ModarezTM MFP available from Synthron, EX 486 available from Troy Chemical, BYK 360P available from BYK Mallinckrodt, and PerenolTM F—30—P available from Henkel.
  • An example of one specific flow aid is an acrylic polymer having a molecular weight of about 17,000 and containing 60 mole percent 2—ethylhexyl methacrylate residues and about 40 mole percent ethyl acrylate residues.
  • the amount of flow aid present is preferably in the range of about 0.5 to 4.0 weight percent, based on the total weight of resin and cross—linking agent.
  • the coarse solid particles included in the mixture have a mean particle size in the range of about 30 ⁇ m to 500 ⁇ m, preferably about 100 ⁇ m to 300 ⁇ m.
  • Pulverization to form the coarse particles can be accomplished using any of several types of mills such as, for example, a Henschel mixer and/or a hammer mill.
  • the coarse grinding may be carried out by agitating an aqueous suspension of the solids in a blender.
  • Slurry coating compositions dispersed in water that are prepared by mixing resin pellets or granules with water and crushing the mixture with a ball mill, pot mill, or crusher are disclosed in JP52107033A and JP80004341B.
  • the resulting coarse particles, suspended in an aqueous liquid phase comprising water and a surfactant, or dispersing agent, are milled at a temperature of up to about 40°C to a mean particle size of about 0.1 ⁇ m to 15 ⁇ m, preferably about 0.5 ⁇ to 5 ⁇ .
  • This fine grinding may be carried out, for example, by media milling. Media milling can be conveniently accomplished with a Netsch LMZ horizontal recirculating mill.
  • the dry coarse particles obtained as described above can be jet milled to produce very fine particles, which are then dispersed in the aqueous liquid phase. Jet milling can be performed using a Trost air impact pulverizer.
  • the surfactant can be ionic, for example, sodium dodecyl sulfate, or preferably, a nonionic compound such as a polyether alcohol.
  • Suitable surfactants include TritonTM X-100 (from Union Carbide Co.), and SurfynolTM GA and CT—136 (from Air Products Corp.).
  • Useful concentrations of solid particles range from about 1 to 50 weight percent, preferably from about 5 to 25 weight percent, of the aqueous liquid phase.
  • Useful concentrations of surfactant range from about 0.1 to 20 weight percent, preferably from about 2 to 10 weight percent, of the liquid phase.
  • Particle size distribution and mean particle size in compositions prepared according to the method of invention can be determined by means of a Microtrac particle size analyzer (available from Leeds & Northrup) , using a technique that entails the measure ⁇ ment of the amount and angle of forward scattered light from a laser beam projected through a stream of particles.
  • the liquid coating compositions prepared according to the method of this invention may be used to coat articles of various shapes and sizes constructed of materials such as glass, ceramics and metals.
  • the compositions are especially useful for producing coatings on articles constructed of metals and metal alloys, particularly steel articles. It is possible to cure some systems at temperatures as low as 115°C, for example, compositions containing epoxy resins, anhydride cross—linking agents, and quaternary ammonium salt or hydroxide cross—linking catalysts, as taught by U.S. Patent No. 5,244,944, the disclosures of which are incorporated herein by reference.
  • Compositions that are curable at relatively low temperatures, around 115°C for example, are useful for coating articles formed of thermoplastic and thermosetting resin compositions.
  • Liquid coating compositions prepared by the method of the present invention are preferably applied to a coating substrate by means of a spray gun typically used with water—based paint compositions. Following spraying, water can be evaporated by air drying at 25— 35°C for about 30 min. to 2h. After removal of water, the substrate is heated at temperatures in the range of about 115° to 200°C for periods of about 5 minutes to 30 minutes. Cure of the coatings can be determined by standard test procedure ASTM 4752—87 and reported as MEK (Methyl Ethyl Ketone) solvent resistance. In this procedure, cotton cheese cloth folded according to specification is attached to the end of a 13—ounce ball peen hammer and saturated with MEK. The hammer is attached to a motorized controller that forces a back and forth sliding action of the cloth—covered hammer ball against the coating surface. Pi coating capable of withstanding 200 back and forth (double) rubs without marring of the coating surface is deemed cured.
  • MEK Metal Ethyl Ketone
  • Example 1 Media milling of mixture for liquid coating composition
  • the ground mixture was dispersed in water containing 5 weight percent of an approximately 1:1 mixture of SurfynolTM CT-136 and SurfynolTM GA surfactants; the resulting suspension contained 39 weight percent solids.
  • Particle size was reduced at ambient temperature, using a Netsch LMZ horizontal recirculating mill charged with 0.8—1.25 mm zirconium silicate media, to a range of about 0.4 ⁇ m to 15 ⁇ m, with a mean particle size of about 4 ⁇ m.
  • a steel panel of dimensions 3 in x 9 in (7.7 cm x 23 cm) was coated with the composition prepared as described in Example 1, using a conventional liquid coating spray gun.
  • the coating was air dried at room temperature for 10 min, then cured for 20 min in an oven at 375°F (191°C) .
  • the cured coating withstood 200 double rubs in the MEK solvent resistance test without marring of the coated surface.

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  • Chemical & Material Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
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Abstract

L'invention concerne un procédé de préparation d'une composition de revêtement liquide. Ledit procédé consiste à: (a) former un mélange composé d'une suspension de particules solides grossières comprenant une résine durcissable et un agent de réticulation réagissant avec ladite résine; les particules solides grossières présentant une grosseur moyenne d'environ 30 νm à 500 νm dans un milieu liquide aqueux composé d'eau et d'un tensioactif; et (b) broyer le mélange à une température non supérieure à environ 40 °C afin d'obtenir une composition de revêtement comprenant une suspension de particules solides fines, dont la grosseur moyenne se situe entre environ 0,1 νm et 15 νm, en suspension dans le milieu liquide aqueux.
PCT/US1995/004320 1994-04-13 1995-04-12 Procede de preparation de compositions de revetement liquides WO1995028448A1 (fr)

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US22714194A 1994-04-13 1994-04-13

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996037561A2 (fr) * 1995-05-19 1996-11-28 Basf Coatings Ag Dispersion aqueuse de peinture pulverulente
WO1997017390A1 (fr) * 1995-11-03 1997-05-15 Basf Coatings Ag Dispersions aqueuses de peinture en poudre
WO1998027141A2 (fr) * 1996-12-18 1998-06-25 Basf Coatings Ag Dispersion de peinture en poudre aqueuse
WO2000069979A2 (fr) * 1999-05-19 2000-11-23 Basf Corporation Composition de revetement en poudre mouillable pour traitement humide
WO2008019149A1 (fr) * 2006-08-11 2008-02-14 Momentive Performance Materials Inc. Composition et procédé associé
CN109627953A (zh) * 2018-12-19 2019-04-16 沈阳派尔化学有限公司 一种水性丙烯酸聚氨酯桔纹漆的制备

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Publication number Priority date Publication date Assignee Title
JPS52107033A (en) * 1976-03-05 1977-09-08 Nippon Paint Co Ltd Method of manufacturing slurry-type water dispersed paint
EP0043104A1 (fr) * 1980-06-27 1982-01-06 Hoechst Aktiengesellschaft Procédé de préparation de laques thermodurcissables et diluables à l'eau pour le revêtement de substrats métalliques et leur utilisation comme agents de revêtement
JPS5865769A (ja) * 1981-10-14 1983-04-19 Dainippon Toryo Co Ltd 水分散型熱硬化性被覆組成物
EP0138051A2 (fr) * 1983-09-14 1985-04-24 Herberts Gesellschaft mit beschränkter Haftung Procédé de préparation de concentrés stockables et leur utilisation dans la fabrication de revêtements
EP0372860A1 (fr) * 1988-12-02 1990-06-13 Courtaulds Coatings (Holdings) Limited Compositions de revêtement en poudre colorées

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Publication number Priority date Publication date Assignee Title
JPS52107033A (en) * 1976-03-05 1977-09-08 Nippon Paint Co Ltd Method of manufacturing slurry-type water dispersed paint
EP0043104A1 (fr) * 1980-06-27 1982-01-06 Hoechst Aktiengesellschaft Procédé de préparation de laques thermodurcissables et diluables à l'eau pour le revêtement de substrats métalliques et leur utilisation comme agents de revêtement
JPS5865769A (ja) * 1981-10-14 1983-04-19 Dainippon Toryo Co Ltd 水分散型熱硬化性被覆組成物
EP0138051A2 (fr) * 1983-09-14 1985-04-24 Herberts Gesellschaft mit beschränkter Haftung Procédé de préparation de concentrés stockables et leur utilisation dans la fabrication de revêtements
EP0372860A1 (fr) * 1988-12-02 1990-06-13 Courtaulds Coatings (Holdings) Limited Compositions de revêtement en poudre colorées

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Title
DATABASE WPI Derwent World Patents Index; AN 77-74996Y[42] *
PATENT ABSTRACTS OF JAPAN vol. 007, no. 155 (C - 175) 7 July 1983 (1983-07-07) *

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU719294B2 (en) * 1995-05-19 2000-05-04 Basf Coatings Aktiengesellschaft Aqueous powder coating dispersion
WO1996037561A3 (fr) * 1995-05-19 1997-02-20 Basf Lacke & Farben Dispersion aqueuse de peinture pulverulente
WO1996037561A2 (fr) * 1995-05-19 1996-11-28 Basf Coatings Ag Dispersion aqueuse de peinture pulverulente
WO1997017390A1 (fr) * 1995-11-03 1997-05-15 Basf Coatings Ag Dispersions aqueuses de peinture en poudre
US6177487B1 (en) 1995-11-03 2001-01-23 Basf Coatings Ag Aqueous powder paint dispersions
US6291579B1 (en) 1996-12-18 2001-09-18 Basf Coatings Ag Aqueous powder-paint dispersion
WO1998027141A3 (fr) * 1996-12-18 1998-08-20 Basf Coatings Ag Dispersion de peinture en poudre aqueuse
WO1998027141A2 (fr) * 1996-12-18 1998-06-25 Basf Coatings Ag Dispersion de peinture en poudre aqueuse
WO2000069979A2 (fr) * 1999-05-19 2000-11-23 Basf Corporation Composition de revetement en poudre mouillable pour traitement humide
WO2000069979A3 (fr) * 1999-05-19 2001-08-02 Basf Corp Composition de revetement en poudre mouillable pour traitement humide
US6360974B1 (en) 1999-05-19 2002-03-26 Basf Corporation Powder slurry coating composition
AU769560B2 (en) * 1999-05-19 2004-01-29 Basf Corporation Powder slurry coating composition
WO2008019149A1 (fr) * 2006-08-11 2008-02-14 Momentive Performance Materials Inc. Composition et procédé associé
CN109627953A (zh) * 2018-12-19 2019-04-16 沈阳派尔化学有限公司 一种水性丙烯酸聚氨酯桔纹漆的制备
CN109627953B (zh) * 2018-12-19 2021-03-26 沈阳派尔化学有限公司 一种水性丙烯酸聚氨酯桔纹漆的制备

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