Classifications

• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/04—Oxygen-containing compounds
  • C08K5/06—Ethers; Acetals; Ketals; Ortho-esters
• • 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
  • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
  • C08J7/04—Coating
  • C08J7/0427—Coating with only one layer of a composition containing a polymer binder
• • 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
  • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
  • C08J7/04—Coating
  • C08J7/043—Improving the adhesiveness of the coatings per se, e.g. forming primers
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/16—Nitrogen-containing compounds
  • C08K5/17—Amines; Quaternary ammonium compounds
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
  • C08L23/26—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers modified by chemical after-treatment
  • C08L23/28—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers modified by chemical after-treatment by reaction with halogens or compounds containing halogen
• • 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
• • 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
• • 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
  • C08J2323/00—Characterised by the use of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Derivatives of such polymers
  • C08J2323/02—Characterised by the use of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Derivatives of such polymers not modified by chemical after treatment
• • 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
  • C08J2423/00—Characterised by the use of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Derivatives of such polymers

Definitions

• This invention relates to aqueous compositions useful as primers useful for enhancing the adhesion of coatings to polyolefin substrates.
• adhesion promoting compositions This problem has previously been overcome by 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 is to use of two different approaches which employ adhesion promoting compositions.
• polyolefins has been to use an adhestion 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.
• 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 an organic solvent, such as xylene or toluene.
• 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 problems for workers applying the primer coating composition.
• polyolefin containing primer coating composition which is substantially free of organic solvents is disclosed in WO90/12656.
• This composition is a five component composition containing a chlorinated polyolefin, a surfactant, an amine, a polyol and water.
• polyol in the composition disclosed in WO/12656 can create a significant toxicity problem, particularly if the polyol is ethylene glycol.
• polyol toxacology In addition to the concers about polyol toxacology,
• volatilization of the polyols during heat curing of the coating can cause polution problems similar to those encountered when organic solvents are used.
• composition of this invention can be thought of as a four component composition containing A) a chlorinated polyolefin having a particular range of molecular weight, softening point and amount of chlorine,
• chlorinated polyolefin having a molecular weight in the range of 9,000 to 45,000, a softening point in the range of 75 to 105°C and an amount of chlorine in the range of 15 to 35 weight percent, based on the weight of the polyolefin.
• These polymers are known in the art and are disclosed in U.S. 3,579,485.
• the chlorinated polyolefin having a molecular weight in the range of 9,000 to 45,000, a softening point in the range of 75 to 105°C and an amount of chlorine in the range of 15 to 35 weight percent, based on the weight of the polyolefin.
• chlorinated polyolefin has a molecular weight in the range of 9,000 to 16,000, a softening point in the range of 80 to 95oC 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.
• the total amount of polyolefin in the composition is not significant as long as the relative amounts of components (B) and (C) are within the ranges for these materials.
• non-ionic surfactant we mean a surfactant which contains no positively or negatively charged functional groups.
• the surfactants can have a molecular weight of up to 500 or even higher and can include polymeric materials.
• the 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 polyethyleneoxy polyols and ethoxylated alkly phenols. Particularly preferred classes of surfactants include alkyl phenoxy
• the surfactant is a primary ethoxylated alcohol having 12 to 15 carbon atoms or a secondary ethoxylated alcohol having 11 to 15 carbon atoms.
• the amount of surfactant is broadly in the range of 18 to 50 weight % and is preferably in the range of 20 to 25 weight %, based on the weight of the chlorinated polyolefin.
• composition of this invention can be a primary
• amine can be aromatic or aliphatic, aliphatic amines are preferred. In a preferred embodiment the aliphatic amine has an amine functionality of between 1 and 3, and optionally contains other oxygen containing functional groups.
• the amines useful in this invention generally have a
• a highly preferred group of amines are primary, secondary and tertiary aliphatic amines having a
• 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
• n 1 or 2 and R 8 , R 9 , R 10 and R 11 are
• 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:
• Preferred amines are morpholine, triethanolamine, ethanolamine, 2-dimethylaminoethanol, triethylamine and ammonium hydroxide. Particularly preferred amines are morpholine and ammonium hydroxide.
• the amount of amine can be in the range of 2 to 10 weight % and preferably is in the range of 4 to 6 weight %, based on the weight of the chlorinated polyolefin.
• compositions of this invention further contain water.
• the amount of water can vary widely depending on numerous factors, such as the needs of the manufacturer, transportation efficiencies and the needs of the
• compositions of this invention are selected from these compounds having the same
• compositions can be manufactured using less water than would 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 are:
• compositions of this invention can contain other materials in major amounts.
• 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 but preferably the compositions are substantially free of organic solvents.
• the compositions of this invention preferably contain less that 10%, more preferably less than 5% and most preferably less than 1% organic
• the preferably small quantity of organic solvent can be present as an impurity or can be present as in intended component of the composition.
• compositions of this invention do not contain
• polyols that are not present in significant quantities in the compositions of this invention include the polyols disclosed in WO/12656.
• 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.
• the compositions of this invention can be prepared according to techniques well known in the art for preparing polyolefin wax emulsions. For example, the compositions can be prepared by introducing the four components into an agitated pressure vessel and
• the agitating the components at a suitable temperature and pressure for a suitable time typically the temperature will be in the range of 100°C to 150°C, the pressure in the range of 14 psi to 70 psi, and the time will be in the range of 10 minutes to 45 minutes.
• the temperature will be in the range of 100°C to 150°C
• the pressure in the range of 14 psi to 70 psi
• the time will be in the range of 10 minutes to 45 minutes.
• compositions can be prepared using a temperature of 120°C, a pressure of 30 psi and a time of 20 minutes.
• compositions of this invention are admixtures which have a particle size suitably small to make the admixtures useful in coating enbodiments. Therefore, the compositions of this invention include not only what some authorizes 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 the invention were prepared from a chlorinated polyolefin, a nonionic surfactant, an amine and sufficient water to produce emulsions having 24 percent, based on the weight of the total composition, of the chlorinated polyolefin.
• the compositions were prepared by introducing the four components into a sealed vessel equipped with a means for agitation. Agitation was started and the contents of the vessel heated to 120°C and the resulting pressure was 30 psi. This temperature and pressure was
• This example illustrates preparation of a
• composition of the invention using a particular
• chlorinated polyolefin one type of nonionic surfactant and a secondary amine.
• the resultant composition was diluted with sufficient additional water to result in a primer coating
• composition composed of 8 percent chlorinated
• polyolefin based on the weight of total composition. This composition was applied to polypropylene. The composition was also applied to a polyolefin which has been modified with an elastomeric polymer. These materials are generally designated in the trade as “thermoplastic olefins” and are abbreviated "TPO”. The composition was applied by spraying and then dried by baking for 10 minutes at 160°F.
• Stability at 75°F for 8 weeks Slight settling Stability at 125°F for 4 weeks: Slight settling Freeze/thaw stability tests were conducted in accordance with ASTM D2243 with visual inspection.
• This example illustrates preparation of a
• composition of the invention using the same chlorinated polyolefin used in Example 1, the same nonionic
• polypropylene and TPO by spraying and then dried by baking for 10 minutes at 160°F.
• Stability at 75°F for 8 weeks Slight settling Stability at 125°F for 4 weeks: Slight settling Freeze/thaw stability tests were conducted in accordance witASTM D2243 with visual inspection.
• This example illustrates preparation of a
• composition of the invention using the same chlorinated polyolefin used in Example 1, the same nonionic
• chlorinated polyolefin based on the weight of total composition. This composition was applied to
• This example illustrates preparation of a
• composition of the invention using the same chlorinated polyolefin used in Example 1, the same nonionic
• chlorinated polyolefin based on the weight of the total composition. This composition was applied to
• polypropylene and TPO by spraying and then dried by baking for 10 minutes at 160°F.
• Stability at 75°F for 8 weeks Slight settling Stability at 125°F for 4 weeks: Slight settling Freeze/thaw stability tests were conducted in accordance with ASTM D2243 with visual inspection.
• This example illustrates preparation of a
• composition of the invention using the same chlorinated polyolefin used in Example 1, another nonionic
• Stability at 75°F for 8 weeks Slight settling Stability at 125°F for 4 weeks: Slight settling Freeze/thaw stability tests were conducted in accordance with ASTM D 2243 with visual inspection. Results of this test were no change after 5 cycles.
• Paint adhesion tests were conducted in accordance with ASTM D 3359-83, Method A. Results of this test were as follows: Paint adhesion on polypropylene: 50%
• This example illustrates preparation of a
• composition of the invention using the same chlorinated polyolefin used in Example 1, another nonionic
• composition composed of 8 percent chlorinated
• composition This composition was applied to
• polypropylene and TPO by spraying and then dried by baking for 10 minutes at 160°F.
• Stability at 75°F for 8 weeks Slight settling Stability at 125°F for 4 weeks: Slight settling Freeze/thaw stability tests were conducted in accordance with ASTM D 2243 with visual inspection.
• This example illustrates preparation of a
• composition of the invention using the same chlorinated polyolefin used in Example 1, the same nonionic
• polypropylene and TPO by spraying and then dried by baking for 10 minutes at 160°F.
• This example illustrates preparation of a
• composition of the invention using the same chlorinated polyolefin used in Example 1, the same nonionic
• chlorinated polyolefin based on the weight of the total composition. This composition was applied to
• polypropylene and TPO by spraying and then dried by baking for 10 minutes at 160°F.
• Stability at 75°F for 8 weeks Slight settling Stability at 125°F for 4 weeks: Slight settling Freeze/thaw stability tests were conducted in accordance with ASTM D 2243 with visual inspection.
• This example illustrates preparation of a
• composition of the invention using the same chlorinated polyolefin used in Example 1, the same nonionic
• chlorinated polyolefin based on the weight of the total composition. This composition was applied to
• polypropylene and TPO by spraying and then dried by baking for 10 minutes at 160°F.
• Stability at 75°F for 8 weeks Slight settling Stability at 125°F for 4 weeks: Slight settling Freeze/thaw stability tests were conducted in accordance with ASTM D 2243 with visual inspection.
• This example illustrates preparation of a
• composition of the invention using the same chlorinated polyolefin used in Example 1, another nonionic
• composition composed of 8 percent chlorinated polyolefin, based on the weight of the total
• composition This composition was applied to
• polypropylene and TPO by spraying and then dried by baking for 10 minutes at 160°F.
• Stability at 75°F for 8 weeks Slight settling Stability at 125°F for 4 weeks: Slight settling Freeze/thaw stability tests were conducted in accordance with ASTM D 2243 with visual inspection.
• This example illustrates preparation of a
• composition of the invention using the same chlorinated polyolefin used in Example 1, a different nonionic surfactant and a secondary anine.
• This example illustrates preparation of a
• composition of the invention using the same chlorinated polyolefin used in Example 1, another nonionic

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• Chemical & Material Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Organic Chemistry (AREA)
• Health & Medical Sciences (AREA)
• Medicinal Chemistry (AREA)
• Polymers & Plastics (AREA)
• General Chemical & Material Sciences (AREA)
• Life Sciences & Earth Sciences (AREA)
• Engineering & Computer Science (AREA)
• Materials Engineering (AREA)
• Wood Science & Technology (AREA)
• Dispersion Chemistry (AREA)
• Paints Or Removers (AREA)

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Citations (3)

• 1992
  • 1992-06-25 EP EP92914881A patent/EP0594691A1/en not_active Withdrawn
  • 1992-06-25 WO PCT/US1992/005393 patent/WO1993001244A1/en not_active Application Discontinuation
  • 1992-06-25 KR KR1019930704085A patent/KR940701432A/ko not_active IP Right Cessation
  • 1992-06-25 CA CA002112230A patent/CA2112230A1/en not_active Abandoned
  • 1992-06-25 JP JP5502255A patent/JPH06509130A/ja active Pending

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