EP0598005A1 - Composition de revetement aqueuse - Google Patents

Composition de revetement aqueuse

Info

Publication number
EP0598005A1
EP0598005A1 EP92917236A EP92917236A EP0598005A1 EP 0598005 A1 EP0598005 A1 EP 0598005A1 EP 92917236 A EP92917236 A EP 92917236A EP 92917236 A EP92917236 A EP 92917236A EP 0598005 A1 EP0598005 A1 EP 0598005A1
Authority
EP
European Patent Office
Prior art keywords
range
weight
percent
polyolefin
composition
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.)
Ceased
Application number
EP92917236A
Other languages
German (de)
English (en)
Inventor
Jonathan Edward Lawniczak
Rex Porter Evans
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.)
Eastman Chemical Co
Original Assignee
Eastman Kodak Co
Eastman Chemical 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 Eastman Kodak Co, Eastman Chemical Co filed Critical Eastman Kodak Co
Publication of EP0598005A1 publication Critical patent/EP0598005A1/fr
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D123/00—Coating compositions based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Coating compositions based on derivatives of such polymers
    • C09D123/26—Coating compositions based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Coating compositions based on derivatives of such polymers modified by chemical after-treatment
    • C09D123/28—Coating compositions based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Coating compositions based on derivatives of such polymers modified by chemical after-treatment by reaction with halogens or compounds containing halogen

Definitions

  • compositions which are useful as primers for enhancing the adhesion of coatings to polyolefin substrates do not contain large guantities of organic solvent.
  • This invention also relates to a process for preparation of these compositions.
  • thermoplastic olefin and polyethylene is typically difficult because polyolefins are substantially
  • adhesion promoting compositions have previously been overcome by the use of two different approaches which employ adhesion promoting compositions.
  • One approach is to use an adhesion promoting composition as a separate primer coating between the polyolefin substrate and the paint. The primer coating adheres adequately to both the polyolefin and the paint and thereby creates a unitary three component structure with the paint as the outer portion of the structure.
  • Another approach to coating polyolefins has been to use an adhesion promoting composition as an additive along with the paint. This technique is sometimes known in the art as use of a "stir in" adhesion promoter. Numerous polymeric materials have been investigated as possible components for such adhesion promoters.
  • Chlorinated polyolefins have been found to be very satisfactory as the polymeric component for primer compositions due to their cost and performance.
  • U.S. 3,579,485, U.S. 4,070,421, U.S. 4,966,947, U.S. 4,962,149 and U.S. 4,954,573 disclose chlorinated polyolefins which are.entirely satisfactory for the polymeric component of adhesion promoting compositions useful for coating polyolefin substrates.
  • chlorinated polyolefins have been used to prepare adhesion promoting compositions which are entirely satisfactory, the chlorinated polyolefins had to be formulated with large quantities of an organic solvent, such as xylene or toluene.
  • an organic solvent such as xylene or toluene.
  • Use of large quantities of an organic solvent is undesirable because unless elaborate solvent recovery methods are employed application of the primer coating composition results in release of the organic solvent into the atmosphere which can result in both pollution problems and health
  • a composition which is comprised of a chlorinated polyolefin, water and other materials and is reported to be useful as a primer coating for polyolefins is
  • a composition which is comprised of two types of polymers, water and other materials and is reported to be useful as a primer coating for polyolefins is
  • composition of this invention can be thought of as a three component composition comprising
  • an amine, a surfactant and an organic solvent may be present in the composition.
  • chlorinated polyolefin having a molecular weight in the range of
  • a chlorinated polyolefin useful in another embodiment of this invention is the chlorinated
  • chlorinated polyolefin is meant to include both of these polymers.
  • the chlorinated polyolefin can comprise a chlorinated polyolefin having a molecular weight in the range of 100,000 to 150,000, a softening point in the range of 80 to 115°C and an amount of chlorine in the range of 20 to 35 percent, based on the weight of the chlorinated polyolefin.
  • the chlorinated polyolefin can comprise a chlorinated polyolefin having a molecular eight in the range of 110,000 to 130,000, a softening point in the range of 95 to 105°C and an amount of chlorine in the range of 25 to 30 percent, based on the weight of the chlorinated polyolefin.
  • the chlorinated polyolefin has a molecular weight in the range of 9,000 to 16,000, a softening point in the range of 80 to 95°C and an amount of chlorine in the range of 18 to 22 percent, based on the weight of the polyolefin.
  • the molecular weight of the chlorinated polyolefin is average number molecular weight.
  • polyolefin in the composition is in the. range of 70 to 30 weight percent, preferably in the range of 70 to 40 weight percent, and more preferably in the range of 70 to 45 weight percent, .based on the combined weight of the chlorinated polyolefin and the carboxylic acid functional resin.
  • the carboxylic acid functional resins useful in this invention can comprise any polymer which has a sufficiently high molecular weight to form an admixture with the chlorinated polyolefin and also has sufficient carboxylic acid functionality to be compatible with the chlorinated polyolefin in the sense it will combine with the chlorinated polyolefin and form the primer coating composition of this invention.
  • the functional resin performs two functions.
  • the resin serves as the medium in which the chlorinated polyolefin can be formed into an admixture having a fluid homogenous character.
  • the carboxylic acid functionality of the resin through neutralization, provides a mechanism for the creating the admixture of the two polymers and the water.
  • important characteristics of the resin are that the resin be compatible enough with the chlorinated polyolefin to make a fluid homogenous mixture and that the resin have acid functionality to allow dispersion through amine neutralization of the acid group.
  • the carboxylic acid functional resin is an alkyd resin, a polyester resin or an acrylic resin. More preferably the carboxylic acid functional resin is either an alkyd resin or an acrylic resin.
  • alkyd resins useful in this invention are well known in the art and are polyesterification products of polyhydric alcohols and poly-functional acids where part of the acid component may be a long chain fatty acid from vegetable oil.
  • poly-functional acids include phthalic anhydride, adipic acid, maleic
  • anhydride isophthalic acid, sebacic acid, azelaic acid, terephthalic acid, trimellitic anhydride, linoleic acid, linolenic acid, -benzoic acid, hexahydrophthalic
  • polyhydric alcohols examples include glycerol,
  • the oil which is used to modify the alkyd resin may come from the group of oils which includes tung, linseed, soya, safflower, castor, corn, cotton seed, peralla, sesame, soybean, cocoanut, dehydrated castor and tall oils.
  • the amount of oil modification in resins useful in the invention can be in the range of ⁇ 45% (short oil alkyds) or in the range of 45 to 65% (medium oil alkyds).
  • the alkyd resins which are useful in the invention can have a number average molecular weight in the range of 300 to 30,000 grams per mole and an acid number greater than 20. More preferably the acid number of the alkyd resin should be in the range 25 to 150.
  • the alkyd resin is a medium oil alkyd having 70 percent non-volatile content, a Gardner viscosity in the range of Z to Z2 and an acid value in the range of 50 to 59.
  • the acrylic resins useful in this invention are well known in the art and are addition polymers which are the reaction products of acrylic monomers which come from a large number of acrylic and methacrylic acids and esters.
  • acids and esters which can be used include acrylic acid, methacrylic acid, styrene, methyl methacrylate, ethyl acrylate, butyl aerylate, methyl acrylate, ethyl methacrylate, butyl methacrylate, 2- hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, butyl acrylate, propyl methacrylate, lauryl
  • the acrylic resins useful in this invention have a number average molecular weight in the range of 400 to 40,000 grams per mole and an acid number greater than 20. More preferably the acrylic resin has an acid number in the range of 25 to 150.
  • the acrylic resin is a solid acrylic oligomer having an acid value in the range of 220 to 250, a ring and ball softening point in the range of 100 to 120°C and an average number molecular weight in the range of 2000 to 3000.
  • polyester resins useful in this invention are well known in the art and are condensation polymers which are the polyesterification product of
  • polyfunctional carboxylic acids examples include phthalic anhydride, isophthalic acid,
  • cyclohexanedicarboxylic acid adipic acid, azelaic acid, maleic anhydride, sebacic acid, terephthalic acid, trimellitic anhydride, linoleic acid, linolenic acid, benzoic acid, hexahydrophthalic anhydride, tetrahydrophthalic anhydride, fumaric acid, 1,4- cyclohexanedicarboxylic acid and succinic acid.
  • polyfunctional alcohols examples include ethylene glycol, neopentyl glycol, diethylene glycol, 1,6- hexanediol, cyclohexanedimethanol, glycerol,
  • trimethylolethane trimethylolpropane, butylene glycol, 1,4-cyclohexanedimethanol, 1,2-propylene glycol, 1,2- propanediol, dipropylene glycol, pentaerythritol and 2,2,4-trimethyl-1,3-pentanediol.
  • polyester resins are those which have a acid number greater than 20. More preferable polyester resins are those which have an acid number in the range 25-150.
  • the amount of the carboxylic acid functional resin is in the range of 30 to 70 weight percent, preferably in the range of 30 to 60, and more preferably in the range of 30 to 55 weight percent, based on the combined weight of the chlorinated polyolefin and the carboxylic acid functional resin.
  • the preferred chlorinated polyolefin is the non-imidized material
  • use of the above described medium oil alkyl having 70 percent nonvolatile content, a Gardner viscosity in the range of Z to Z2 and an acid value in the range of 50 to 59 is a particularly preferred embodiment of the invention.
  • compositions of this invention contain water.
  • the amount of water can vary widely depending on
  • compositions of this invention are selected from these compounds having the same
  • compositions can be manufactured using less water than would be typically be required to apply the compositions as a coating and water can be subsequently added by the customer at a later time to prepare a coating
  • composition This can be done by simply pouring
  • concentration is also often desired if the adhesion promoter composition is to be used as an additive to the paint in order to prevent excessive dilution of the paint.
  • the amount of water can vary widely and there is no upper limit on the amount of water there is a lower limit on the amount of water because there must at least be sufficient water in the composition to result in the formation of an admixture of the four components.
  • the precise amount of water necessary to form the required admixture can vary, generally there must be at least 40 weight % water in the composition, based on the weight of the total composition, in order to form an admixture with pourable viscosity characteristics.
  • compositions of this invention can optionally contain an amine.
  • the amine can be aromatic or aliphatic, aliphatic amines are preferred.
  • the aliphatic amine can be either a primary, secondary or tertiary amine and optionally contains other oxygen containing functional groups.
  • the amines useful in this invention generally have a molecular weight in the range of 20 to 200.
  • a highly preferred group of amines are primary, secondary and tertiary aliphatic amines having a functionality of 1 to 3 which can be generally
  • R 1 R 7 are independently selected from H or straight or branched chain alkyl, hydroxyalkyl, or alkoxylalkyl groups of 1 to 20 carbon atoms; R 1 - R 7 can additionally include a substituted alkyl group, i.e., where one or more of the carbons in the radical is replaced with or has substituted thereon another
  • an amine, ether, hydroxy or - mercapto moiety e.g., tris-(3-aminopropyl) amine.
  • Another group of highly preferred amines within the above classes are those primary, secondary or tertiary aliphatic amines of the above Formulae in which R 1 - R 7 is specifically substituted with or contains one or more hydroxyl (-OH) functionalities.
  • Another group of preferred amines can be
  • Yet another group which comprise amines preferred in the practice of the present invention are primary, secondary and tertiary aliphatic amines with an amine functionality of 1-3 which also contain one or more ether or alkoxy linkages. Such materials are sometimes referred to as poly (oxyalkylene)diamines. Ethoxylated or propoxylated materials are particularly preferred.
  • Exemplary amines preferred for use in the present invention include:
  • N,N-dimethyl-N'-ethylethylenediamine N,N'-dimethyl-1-,6-hexanediamine
  • N-isopropylethylenediamine N'-isopropyl-2-methyl-1,2-propanediamine;
  • Preferred amines are ammonium hydroxide
  • carboxylic acid functional resin is an alkyd resin a particularly preferred amine is ammonium hydroxide.
  • carboxylic acid functional resin is an acrylic a preferred amine is dimethylethanolamine.
  • the amount of amine can be in the range of 0 to 20 weight percent, preferably in the range of 10 to 20 weight percent, based on the combined weights of the chlorinated polyolefin and carboxylic acid functional resin.
  • the surfactants useful in this invention include both non-ionic and cationic surfactants.
  • non-ionic surfactant we mean a surfactant which contains no positively or negatively charged functional groups.
  • cationic surfactant we mean a surfactant which ionizes in water to produce a large positively charged ion and a small negatively charged ion.
  • the non-ionic surfactants can have a molecular weight of up to 500 or even higher and can include polymeric materials.
  • surfactants include materials which contain groups of varying polarity whereby one part of the molecule is hydrophilic and the other part of the molecule is hydrophobic. Examples of such materials include
  • non-ionic surfactants include alkyl phenoxy poly (ethyleneoxy) alcohols, primary ethoxylated alcohols and secondary ethoxylated alcohols.
  • the non-ionic surfactant is an alkyl phenoxy poly (ethyleneoxy) alcohol having 22 to 215 carbon atoms.
  • the cationic surfactants useful in this invention have a molecular weight in the range of 100 to 1000 and can be broadly be described as alkoxylated amines.
  • the cationic surfactant is an alkoxylated fatty amine or an akloxylated tallow amine.
  • the amount of surfactant is broadly in the range of 1 to 30 weight percent, based on the combined weight of the chlorinated polyolefins and carboxylic acid
  • compositions can contain other materials in major amounts.
  • the compositions of this invention can contain materials typically used in the paint industry to prepare paint formulations, such as thickeners, wetting agents and flow aids, pigments, resins and solvents.
  • compositions can contain organic solvents as long as the amount of organic solvent is not large.
  • compositions of this invention preferably contain less than 50%, more preferably less than 25% organic solvent based, on the weight of the composition.
  • compositions of this invention can be used as aa adhesion promoting composition according to two different approaches. Selection of the preferred approach depends on numerous factors, such as the specific characteristics of the paint, the particular substrate to be painted, the nature and extent of the other materials to be used in the paint formulation and other factors.
  • the coating compositions of this invention can be used as a separate primer coat by preferably diluting the
  • compositions of this invention can be used as a so-called "stir-in" paint additive.
  • the composition is added admixed with the paint and the resulting admixture is applied to the polyolefin substrate to form a single coating which adheres to the polyolefin substrate.
  • compositions of this invention are admixtures which have a particle size suitably small to make the admixtures useful in coating embodiments. Therefore, the compositions of this invention include not only what some authorities call “emulsions” and “dispersions” but include as well as all other physical forms in which the various components can be become admixed. For example, some authorities characterize water containing
  • compositions of this invention are particularly useful as adhesion promoters to enhance the adhesion of paints to polyolefin substrates it is within the scope of the invention for the compositions to be used by themselves as a paint to form a final protective coating which not only protects the substrate but also is decorative as a result of the addition of pigments.
  • compositions of this invention are prepared by a novel process comprised of two steps. First an admixture of the chlorinated polyolefin and carboxylic acid functional resin is prepared and then an admixture is prepared composed of the admixture of the polyolefin and resin and water.
  • the chlorinated polyolefin and carboxylic acid functional resin can be prepared into an admixture by methods well known in the art by preparing admixtures of polymeric materials. If the chlorinated polyolefin and carboxylic acid functional resins are both solids they can be admixed in a double screw extruder or can be powdered and the mixed powders extruded in a single screw extruder. Additionally the admixture can be prepared by combining the resin and chlorinated
  • polyolefin on a hot roll mill such as a hot three roll mill.
  • the admixture can be cooled and then pulverized to a powder prior to addition of the other materials.
  • chlorinated polyolefin is a solid and the carboxylic acid functional resin is a liquid or
  • the admixture can be prepared by heating the mixture above the softening point of the chlorinated polyolefin and stirring the chlorinated polyolefin and the resin together.
  • the chlorinated polyolefin can be mixed with the resin by applying high-shear mixing.
  • polyolefin and carboxylic acid functional resin can be prepared by methods well known in the art for preparing admixtures of polymers and water. According to one method the admixture is prepared by subjecting the materials to high shear in a vessel equipped with a means to create high shear, such as a stirrer.
  • compositions of the invention were prepared from a chlorinated polyolefin, a carboxylic acid functional resin, water and optionally an amine, a surfactant and an organic solvent.
  • the chlorinated polyolefin and the carboxylic acid functional resin were introduced into a vessel equipped with means to agitate the materials.
  • Paint adhesion tests of selected compositions were conducted in accordance with ASTM D 3359-83, Method A. Paint adhesion tests were conducted by applying the composition to polypropylene and to a polyolefin which had been modified with an elastomeric polymer. These materials are generally designated in the trade as
  • thermoplastic olefins and are abbreviated “TPO”.
  • TPO thermoplastic olefins
  • the composition was applied by spraying and then dried at room temperature.
  • a commercially available automotive paint system was applied and baked 30 minutes at 250°F.
  • This example illustrates preparation of a
  • composition of the invention using a particular chlorinated polyolefin, a particular carboxylic acid functional resin, water and an amine.
  • An admixture was prepared composed of 50 grams of a chlorinated, non-imidized polyolefin which has a
  • carboxylic acid functional resin which is a medium oil alkyd resin (70% solids) having an acid number in the range of 50 to 59.
  • the admixture was heated for 2 hours at 105°C. 10 grams of ammonium hydroxide (28%) and 200 grams of water were then added and an admixture formed by high shear agitation for 10 minutes.
  • the resultant composition was diluted with sufficient additional water to result in a primer coating composition typical of that used in the trade and paint adhesion tests were conducted with the following results.
  • This example illustrates preparation of a
  • composition of the invention using different amounts of the same materials used in Example 1.
  • An admixture was prepared composed of 30 grams polyolefin and 70 grams of alkyd resin. The admixture was heated for 1 hour at 121°C. 8 grams of ammonium hydroxide (28%) and 150 grams of water were then added and an admixture formed by high shear agitation for 10 minutes. The result of a stability test at 25°C for 8 weeks was slight settling. The composition was diluted with sufficient additional water to result in a primer coating composition typical of that used in the trade and paint adhesion tests were conducted with the following results.
  • This example illustrates preparation of a
  • An admixture was prepared composed of 50 grams polyolefin and 50 grams of alkyd resin. The admixture was heated for 2 hours at 121°C. 4 grams of
  • This example illustrates preparation of a
  • composition of the invention using a different amount of the same materials used in Example 3.
  • An admixture was prepared composed of 70 grams polyolefin and 30 grams of alkyd resin. The admixture was heated for 12 hours at 121°c. 2 grams of
  • This example illustrates preparation of a
  • composition of the invention using different amounts of the same materials used in Example 1.
  • An admixture was prepared composed of 25 grams polyolefin and 25 grams of alkyd resin. The admixture was heated for 2 hours at 121°C. The 10g ammonium hydroxide (28%) and 10.0g water were then added and an admixture formed by high shear agitation for 10 minutes. The result of a stability test at 25°C for 6 weeks was slight settling. The composition was diluted with sufficient additional water to result in a primer coating composition typical of that used in the trade and paint adhesion tests were conducted with the
  • This example illustrates preparation of a
  • composition of the invention using different amounts of the same materials used in Example 5.
  • An admixture was prepared composed of 35 grams polyolefin and 15 grams of alkyd resin. The admixture was heated for 2 hours at 121°C. 5 grams of ammonium hydroxide (28%) and 100 grams of water were then added and an admixture formed by high shear agitation for 10 minutes. The result of a stability test at 25°C for 6 weeks was heavy settling. The composition was diluted with sufficient additional water to result in a primer coating composition typical of that used in the trade and paint adhesion tests were conducted with the following results.
  • This example illustrates preparation of a
  • composition of the invention using different amounts of the same materials used in Example 5.
  • An admixture was prepared composed of 25 grams polyolefin and 25 grams of alkyd resin. The admixture was heated for 2 hours at 121°C. 1 gram of ammonium hydroxide (28°) and 100 grams of water were then added and an admixture formed by high shear agitation for 10 minutes. The result of a stability test at 25°C for 6 weeks was heavy settling. The composition was diluted with sufficient additional water to result in a primer coating composition typical of that used in the trade and paint adhesion tests were conducted with the following results. Polypropylene 0% adhesion
  • This example illustrates preparation of a
  • composition of the invention using a different
  • An admixture was prepared composed of 50 grams polyolefin and 50 grams of a chain stopped alkyd resin (70% solids) with 35 acid number. The admixture was heated for 10 minutes at 121°C. 8 grams of ammonium hydroxide (28%) and 100 grams of water were then added and an admixture formed by high shear agitation for 10 minutes. The result of a stability test at 25°C for 8 weeks was heavy settling. The composition was diluted with sufficient additional water to result in a primer coating composition typical of that used in the trade and paint adhesion tests were conducted with the
  • This example illustrates preparation of a
  • composition of the invention using a different
  • Example 8 carboxylic acid functional resin than used in Example 8.
  • An admixture was prepared composed of 30 grams polyolefin and 70 grams of an acrylic resin (65% solids) with 90 acid number. The admixture was heated for 2 hours at 12i°C. 6 grams of ammonium hydroxide (28%) and 100 grams of water were then added and. an admixture formed by high shear agitation for 10 minutes. The composition was diluted with sufficient additional water to result in a primer coating composition typical of that used in the trade and paint adhesion tests were conducted with the following results.
  • This example illustrates preparation of a
  • composition of the invention using a chlorinated
  • polyolefin a carboxylic acid functional resin, an amine, a surfactant and water.
  • An admixture was prepared composed of 50 grams polyolefin and 50 grams of an alkyd resin with 85 acid number. The admixture was heated for 2 hours at 121°C. 4 grams of dimethylethanolamine, 1 gram of a nonyl phenoxy poly (ethyleneoxy) alcohol having an HBL value in the range of 13 to 14 and 200 grams of water were then added and an admixture formed by high shear agitation for 10 minutes. The result of a stability test for 2 weeks and 25°C was heavy settling. The composition was diluted with sufficient additional water to result in a primer coating composition typical of that used in the trade and paint adhesion tests were conducted with the following results.
  • This example illustrates preparation of a
  • composition of the invention similar to that prepared in Example 10 except a different carboxylic acid functional resin was used.
  • An admixture was prepared composed of 50 grams polyolefin and 50 grams of a acrylic resin (60% solids) with 90 acid number. The admixture was heated for 2 hours at 121°C. 4 grams of dimethylethanolamine, 2 grams of an alkyl phenoxy poly(ethyleneoxy) alcohol and 200 grams of water were then added and an admixture formed by high shear agitation for 10 minutes. The result of a stability test for 2 weeks and 25°C was no change. The composition was diluted with sufficient additional water to result in a primer coating
  • composition typical of that used in the trade and paint adhesion tests were conducted with the following
  • This example illustrates preparation of a
  • composition of the invention similar to that prepared in Example 10 except a different carboxylic acid functional resin was used.
  • An admixture was prepared by subjecting to high shear 50 grams polyolefin and 50 grams of an acrylic resin (70% solids) with acid number 45. 4 grams of dimethylethanolamine, 2 grams of an alkyl phenoxy poly (ethyleneoxy) alcohol and 200 grams of water were then added and an admixture formed by high shear
  • This example illustrates preparation of a
  • composition of the invention composed of a chlorinated polyolefin, a carboxylic acid functional resin, an amine and water.
  • An admixture was prepared by subjecting to high shear 50 grams polyolefin and 50 grams of an acrylic resin (80% solids) with acid number 35. 4 grams of dimethylethanolamine and 200 grams of water were then added and an admixture formed by high shear agitation for 10 minutes. The result of a stability test for 2 weeks and 25°C was heavy settling. The composition was diluted with sufficient additional water to result in a primer coating composition typical of that used in the trade and paint adhesion tests were conducted with the following results.
  • This example illustrates preparation of a
  • composition of the invention similar to Example 12 except that a different carboxylic acid functional resin was used.
  • An admixture was prepared by subjecting to high shear 50 grams polyolefin and 50 grams of an alkyd resin (80% solids) with acid number 34. 4 grams of
  • This example illustrates preparation of a
  • composition of the invention similar to Example 14 except that a different carboxylic acid functional resin was used.
  • An admixture was prepared by subjecting to high shear 50 grams polyolefin and 50 grams of a saturated polyester resin (75% solids) with acid number 68. 4 grams of dimethylethanolamine, 2 grams of an alkyl phenoxy poly(ethyleneoxy) alcohol and 200 grams of water were then added and an admixture formed by high shear agitation for 10 minutes. The result of a stability test for 2 weeks and 25°C was reversible phase
  • This example illustrates preparation of a
  • composition of the invention similar to Example 15 except that a different carboxylic acid functional resin was used.
  • An admixture was prepared by subjecting to high shear 50 grams polyolefin and 50 grams of an saturated polyester resin (85% solids in xylene) with an acid number in the range of 24 to 34. 4 grams of
  • This example illustrates preparation of a
  • composition of the invention composed of a chlorinated polyolefin, a carboxylic acid functional resin, an amine, a surfactant, an organic solvent and water.
  • An admixture was prepared by subjecting to high shear 50 grams polyolefin and 50 grams of an acrylic modified polyester resin (50% solids) with acid value in the range of 58 to 66. 4 grams of dimethylethanolamine, 4 grams of an alkyl phenoxy poly(ethyleneoxy) alcohol, 4 grams of xylene and 200 grams of water were then added and an admixture formed by high shear agitation for 10 minutes. The result of a stability test for 2 weeks and 25°C was slight settling. The composition was diluted with sufficient additional water to result in a primer coating composition typical of that used in the trade and paint adhesion tests were conducted with the
  • This example illustrates preparation of a
  • composition of the invention similar to Example 16 except that a different carboxylic acid functional resin was used.
  • An admixture was prepared by subjecting to high shear 50 grams polyolefin and 50 grams of an acrylic resin (70% solids) with acid number. 4 grams of dimethylethanolamine, 2 grams of an alkyl phenoxy poly (ethyleneoxy) alcohol and 200 grams of water were then added and an admixture formed by high shear
  • This example illustrates preparation of a
  • composition of the invention composed of a chlorinated polyolefin, a carboxylic acid functional resin, an amine, a surfactant, an organic solvent and water.
  • An admixture was prepared by combining on a 3 roll mill 13 grams of an imidized chlorinated polyolefin which has a molecular weight in the range of 9 , 000 to 16,000, a softening point in the range of 80 to 95°C and an amount of chlorine in the range of 18 to 22 percent, based on the weight of the polyolefin, 13 grams of a solid acrylic resin with acid number 230.
  • the admixture was cooled and pulverized into granules and the granules heated at 121°C for 1 hour.
  • This example illustrates preparation of a
  • composition of the invention composed of a chlorinated polyolefin, a carboxylic acid functional resin, an amine, an organic solvent and water.
  • An admixture was prepared by combining at 66°C 50 grams of a chlorinated polyolefin having a molecular weight in the range of 100,000 to 150,000, a softening point in the range of 80 to 115°C and an amount of chlorine in the range of 20 to 35 percent, based on the weight of the polyolefin, 50 grams of a carboxylic acid functional resin which is an alkyd resin (70% solids) having an acid number in the range of 50 to 59, and 50 grams of xylene. 10 grams of dimethylethanolamine and 250 grams of water were then added and an admixture formed by high shear agitation for 10 minutes. The result of a stability test for 3 weeks and 25°C was slight settling. The composition was diluted with sufficient additional water to result in a primer coating composition typical of that used in the trade and paint adhesion tests were conducted with the following results.
  • This example illustrates preparation of a
  • composition of the invention composed of a chlorinated polyolefin, a carboxylic acid functional resin, an amine, an organic solvent and water.
  • An admixture was prepared by combining at 66°C 50 grams of a chlorinated polyolefin having a molecular weight in the range of 110,000 to 130,000, a softening point in the range of 95 to 105°C and an amount of chlorine in the range of 25 to 30 percent, based on the weight of the polyolefin, 50 grams of a carboxylic acid functional resin which is an alkyd resin (70% solids) having an acid number in the range of 50 to 59, and 50 grams of xylene. 10 grams of dimethylethanolamine and 250 grams of water were then added and an admixture formed by high shear agitation for 10 minutes. The result of a stability test for 3 weeks and 25°C was no change. The composition was diluted with sufficient additional water to result in a primer coating
  • composition typical of that used in the trade and paint adhesion tests were conducted with the following results.

Abstract

Composition comprenant: (A) une polyoléfine chlorée, (B) une résine fonctionnelle d'acide carboxylique, et (C) de l'eau.
EP92917236A 1991-08-05 1992-07-30 Composition de revetement aqueuse Ceased EP0598005A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US74035291A 1991-08-05 1991-08-05
US740352 1991-08-05
PCT/US1992/006286 WO1993003104A1 (fr) 1991-08-05 1992-07-30 Composition de revetement aqueuse

Publications (1)

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EP0598005A1 true EP0598005A1 (fr) 1994-05-25

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EP92917236A Ceased EP0598005A1 (fr) 1991-08-05 1992-07-30 Composition de revetement aqueuse

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EP (1) EP0598005A1 (fr)
JP (1) JPH06509383A (fr)
CA (1) CA2107328A1 (fr)
WO (1) WO1993003104A1 (fr)

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US5777022A (en) * 1996-05-16 1998-07-07 Bee Chemical Company One-coat, waterborne coating system for untreated polypropylene-based substrates
TW364002B (en) 1995-11-15 1999-07-11 Bee Chemical Co A one-coat, waterborne coating system for untreated polypropylene-based substrates
JP3738876B2 (ja) * 1999-06-22 2006-01-25 本田技研工業株式会社 自動車内装材用水性塗料組成物
JP3831161B2 (ja) * 1999-11-15 2006-10-11 本田技研工業株式会社 水性プライマー塗料組成物および塗装物
JP2001220474A (ja) * 1999-11-30 2001-08-14 Takeda Chem Ind Ltd 水系エマルション組成物および接着性組成物
US6303685B1 (en) 2000-04-25 2001-10-16 3M Innovative Properties Company Water dispersed primers
US6780908B1 (en) 2000-06-21 2004-08-24 E. I. Du Pont De Nemours And Company Coating composition
US6433085B1 (en) 2000-06-21 2002-08-13 E.I. Du Pont De Nemours And Company Coating composition
US7163981B2 (en) 2004-08-04 2007-01-16 Toyota Technical Center, U.S.A, Inc. Et Al. Aqueous paint composition and uses thereof
JP5308165B2 (ja) 2006-02-01 2013-10-09 チバ ホールディング インコーポレーテッド ポリマーのための安定剤組成物
CN101589101B (zh) * 2006-12-13 2013-07-17 日本制纸化学株式会社 聚烯烃树脂分散组合物和其制备方法
JP5472727B2 (ja) * 2010-02-17 2014-04-16 Ｄｉｃ株式会社 水性樹脂分散体及びこれを含有する塗料
JP6662039B2 (ja) * 2013-11-26 2020-03-11 東洋紡株式会社 変性ポリオレフィン含有水性分散体組成物
WO2015079919A1 (fr) * 2013-11-26 2015-06-04 東洋紡株式会社 Composition de type dispersion aqueuse contenant une polyoléfine modifiée
WO2022202131A1 (fr) * 2021-03-24 2022-09-29 関西ペイント株式会社 Composition aqueuse de revêtement d'apprêt, et procédé de formation d'un film de revêtement multicouche

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GB539416A (en) * 1938-12-31 1941-09-10 Standard Oil Dev Co An improved manufacture of resins and of coating compositions containing such resins
JPH0762127B2 (ja) * 1987-12-28 1995-07-05 三井石油化学工業株式会社 水分散型接着剤
US4966947A (en) * 1988-05-20 1990-10-30 Eastman Kodak Company Modified chlorinated polyolefins
DE3910901A1 (de) * 1989-04-04 1990-10-11 Ppg Ind Deutschland Gmbh Verfahren zur herstellung einer waesserigen feinteiligen dispersion eines chlorierten polyolefins und verwendung derselben in waesserigen beschichtungszusammenetzungen

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Title
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Also Published As

Publication number Publication date
WO1993003104A1 (fr) 1993-02-18
JPH06509383A (ja) 1994-10-20
CA2107328A1 (fr) 1993-02-06

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