WO2005121259A2 - Adhesion promoter for plastics - Google Patents

Adhesion promoter for plastics Download PDF

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Publication number
WO2005121259A2
WO2005121259A2 PCT/EP2005/052569 EP2005052569W WO2005121259A2 WO 2005121259 A2 WO2005121259 A2 WO 2005121259A2 EP 2005052569 W EP2005052569 W EP 2005052569W WO 2005121259 A2 WO2005121259 A2 WO 2005121259A2
Authority
WO
WIPO (PCT)
Prior art keywords
additive
coating composition
coating
weight
adhesion promoter
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
PCT/EP2005/052569
Other languages
English (en)
French (fr)
Other versions
WO2005121259A3 (en
Inventor
Ingrid Frieda Martha Walther
Lavonne Wynette Swift
Latoska Nikita Price
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.)
Akzo Nobel Coatings International BV
Original Assignee
Akzo Nobel Coatings International BV
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 Akzo Nobel Coatings International BV filed Critical Akzo Nobel Coatings International BV
Priority to JP2007513967A priority Critical patent/JP2008501813A/ja
Priority to EP20050752644 priority patent/EP1756235A2/en
Priority to AU2005252376A priority patent/AU2005252376A1/en
Priority to CA 2568853 priority patent/CA2568853A1/en
Priority to BRPI0511821-2A priority patent/BRPI0511821A/pt
Priority to KR1020067027554A priority patent/KR20070034531A/ko
Priority to MXPA06014177A priority patent/MXPA06014177A/es
Publication of WO2005121259A2 publication Critical patent/WO2005121259A2/en
Publication of WO2005121259A3 publication Critical patent/WO2005121259A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F255/00—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00
    • C08F255/02—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00 on to polymers of olefins having two or three carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F255/00—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00
    • C08F255/02—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00 on to polymers of olefins having two or three carbon atoms
    • C08F255/023—On to modified polymers, e.g. chlorinated polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/2805—Compounds having only one group containing active hydrogen
    • C08G18/2815—Monohydroxy compounds
    • C08G18/282—Alkanols, cycloalkanols or arylalkanols including terpenealcohols
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/2805—Compounds having only one group containing active hydrogen
    • C08G18/2815—Monohydroxy compounds
    • C08G18/282—Alkanols, cycloalkanols or arylalkanols including terpenealcohols
    • C08G18/2825—Alkanols, cycloalkanols or arylalkanols including terpenealcohols having at least 6 carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/2805—Compounds having only one group containing active hydrogen
    • C08G18/288—Compounds containing at least one heteroatom other than oxygen or nitrogen
    • C08G18/289—Compounds containing at least one heteroatom other than oxygen or nitrogen containing silicon
    • 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
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L51/00—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
    • C08L51/06—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers grafted on to homopolymers or copolymers of aliphatic hydrocarbons containing only one carbon-to-carbon double bond
    • 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
    • C09D151/00—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
    • C09D151/06—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers grafted on to homopolymers or copolymers of aliphatic hydrocarbons containing only one carbon-to-carbon double bond
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
    • 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
    • C09D5/002—Priming paints
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J123/00—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers
    • C09J123/26—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers modified by chemical after-treatment
    • C09J123/28—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers modified by chemical after-treatment by reaction with halogens or compounds containing halogen
    • C09J123/286—Chlorinated polyethylene
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J151/00—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers
    • C09J151/06—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers grafted on to homopolymers or copolymers of aliphatic hydrocarbons containing only one carbon-to-carbon double bond
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D2201/00—Polymeric substrate or laminate
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D7/00—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials
    • B05D7/02—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials to macromolecular substances, e.g. rubber
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D7/00—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials
    • B05D7/50—Multilayers
    • B05D7/56—Three layers or more
    • B05D7/57—Three layers or more the last layer being a clear coat
    • B05D7/576—Three layers or more the last layer being a clear coat each layer being cured, at least partially, separately
    • 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
    • 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
    • C08J2467/00—Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers
    • 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
    • C08K5/05—Alcohols; Metal alcoholates
    • 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
    • C08K5/54—Silicon-containing compounds
    • C08K5/541—Silicon-containing compounds containing oxygen
    • C08K5/5435—Silicon-containing compounds containing oxygen containing oxygen in a ring
    • 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 halogen-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
    • C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
    • C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
    • C08L2666/14—Macromolecular compounds according to C08L59/00 - C08L87/00; Derivatives thereof
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]

Definitions

  • the present invention relates to an adhesion promoter additive, and to a coating composition suitable for use with a variety of plastic components, including thermoplastic polyolefin (TPO).
  • the coating composition comprises the adhesion promoter additive having (a) at least one modified polyolefin and (b) at least one monohydric alcohol, at least one epoxy-fu notional silane, or a mixture thereof. Substrates painted with the coating composition are also disclosed.
  • the composition of the present invention is particularly useful as a primer for plastic components in the automotive industry.
  • Plastics are used in wide variety of applications, including containers, household appliances, automobile parts and accessories, and other commercial items. With respect to the automotive industry, the use of plastic components has increased dramatically over the past several decades. The quest for lighter, more fuel efficient cars has led automotive manufacturers to utilize plastics in an increasing number of interior and exterior applications, such as airbag covers, bumpers, fascias, fenders, door panels, panel hoods, panel roofs, and panel trunk lids. Besides generally being low cost, plastics are also low weight, corrosion resistant, impact resistant, relatively easy to mold, and recyclable. Because of these and other advantages derived from their use, it is inevitable that more and more automotive parts will be produced from plastics.
  • plastic for automotive components
  • polymeric substrates made from a variety of thermoplastic and thermosetting materials can have widely varying surface properties, such as surface tension, roughness, and flexibility, which can make strong adhesion of coatings difficult, particularly after aging or environmental exposure.
  • the plastic in order to use a polyurethane primer on a plastic during automotive repair, the plastic must first be identified, e.g. type, flexibility, etc., by performing such activities as the "burn" test or by checking an identification system in order to determine the appropriate process for coating the plastic.
  • Thermoplastic olefin (TPO), an alloy of polypropylene and an elastomer, is one type of plastic commonly used in the automotive industry.
  • TPO Thermoplastic olefin
  • the structure of this polymer results in a surface that most coatings will not wet out or adhere to. Therefore, the surface must be physically or chemically altered in order for it to be coated with most currently available coating technology, but each of these surface pretreatments has its own disadvantages.
  • Plasma treatment or corona discharge employs ionized gases to oxidize the surface and can be difficult and costly. Flame treatment also oxidizes the surface but requires a precise distance of flame that is difficult to achieve on a production line. Etching is another way of preparing the surface. However, the etching chemicals can be toxic or the subject of environmental concerns.
  • coating compositions that exhibit acceptable adhesion directly to polymeric materials, such as TPO, without the use of separate adhesion promoter layers or tie coats have been developed.
  • polyolefin diols have been used in coating compositions to improve adhesion to polymeric substrates without the use of separate adhesion promoter layers or tie coats.
  • U.S. Patent US 6001469 herein incorporated by reference, discloses a coating composition containing a saturated polyhydroxylated polydiene polymer having terminal hydrpxyl groups.
  • U.S. Patent US 4863988 also incorporated by reference herein, relates to a curable paint composition containing a curable film-forming resin and a chlorinated and graft-modified polypropylene.
  • an adhesion promoter additive comprising: (A) at least one modified olefin; and (B) at least one component selected from the group consisting of monohydric alcohols, epoxy-functional silanes, and mixtures thereof.
  • the invention also relates to coating compositions comprising the adhesion promoter additive.
  • One such coating composition comprises at least one hydroxyl- functional film forming polymer and at least one polyisocyanate compound as well as the adhesion promoter additive.
  • the invention also relates to a method of coating a plastic substrate by applying a coating composition comprising the adhesion promoter additive onto a plastic substrate and curing the coating composition and to plastic articles coated with such a coating composition.
  • the present invention is also applicable to other industries as suggested above, which utilize coated plastic substrates.
  • the current invention relates to an adhesion promoter additive and to a coating composition comprising the adhesion promoter additive.
  • the coating composition additionally comprises at least one hydroxyl-functional film forming polymer and at least one polyisocyanate compound.
  • the adhesion promoter additive comprises (A) at least one modified polyolefin and (B) at least one component selected from the group consisting of monohydric alcohols, epoxy- functional silanes, and mixtures thereof.
  • the amount of the adhesion promoter additive incorporated into the coating composition is in the range of 20 % to 40 % by volume, more preferably 25 % to 35 % by volume, based on the total volume of the coating composition.
  • the hydroxyl-functional film forming polymer preferably has a hydroxyl value between 50 and 300 mg KOH/g based on solids content of the polymer, and more preferably between 70 and 200 mg KOH/g.
  • the number average molecular weight preferably does not exceed 6000 and more preferably does not exceed 4500.
  • the polydispersity is preferably between about 1.1 to about 5 and more preferably between about 1.1 and about 3.
  • the acid value of the polymer is preferably less than or equal to 50 mg KOH/g based on solids content of the polymer.
  • suitable hydroxyl-functional film forming polymers include polyesters, polyacrylates, polyvinyl, polyurethanes, polycarbonates or polyamides. In one preferred embodiment, the polymer is a polyacrylate polyol.
  • the polyisocyanate compound is a polyisocyanate having two or more, preferably two to four isocyanate groups.
  • useful polyisocyanate compounds include toluene diisocyanate, methylene bis(4-cyclohexylisocyanate), isophorone diisocyanate and its isocyanurate or adducts, hexamethylene diisocyanate and its isocyanurate, biuret, urethdione, and allophanate, and meta-tetramethylxylene diisocyanate and the adduct thereof with trimethylolpropane.
  • the present coating composition further comprises an adhesion promoter additive, which comprises at least one modified polyolefin.
  • an adhesion promoter additive which comprises at least one modified polyolefin.
  • the amount of modified polyolefin in the additive is between 10 % by weight and 30 % by weight, based on the weight of the additive.
  • One particularly preferred polyolefin is chlorinated polyolefin, also known as CPO.
  • Chlorinated polyolefins suitable for use in the present invention preferably have a chlorine content between 15 % by weight and 60 % by weight, based on the total solid weight of the final chlorinated polyolefin, and more preferably between 18 % by weight and 23 % by weight.
  • the chlorinated polyolefin preferably has a weight average molecular weight between 5000 and 200000, more preferably, between 10000 and 40000.
  • the chlorinated polyolefin may be solid, in powder or pelletized form, or in solution.
  • any chlorinated polyolefin known to those skilled in the art to be an adhesion promoter may be used, for example chlorinated polypropylene, chlorinated polybutylene, chlorinated polyethylene, and mixtures thereof.
  • One suitable chlorinated polyolefin is CPO-343-1, available commercially from Eastman Chemical Company of Kingsport, Tennessee, USA.
  • Other suitable chlorinated polyolefins are described in U.S. Patent Nos. US 4997882; US 5319032; and US 5397602, herein incorporated by reference.
  • modified polyolefins include, for example, AP 440-1, a non- chlorinated polyolefin available commercially from Eastman Chemical Company of Kingsport, Tennessee, USA. More generally, if non-chlorinated, the modified polyolefin must have sufficient solubility for inclusion into a primer formulation, a low film formation temperature, and a high level of acid functional ization, i.e. an acid number of at least 40 mg KOH/g. Preferably, the modified polyolefin is capable of being heat cured.
  • the adhesion promoter also comprises at least one component selected from the group consisting of monohydric alcohols, epoxy-functional silanes, and mixtures thereof.
  • monohydric alcohol is used throughout the specification to describe a linear, cyclic, aromatic, or branch-chained hydrocarbon having a single hydroxyl group located at one terminus of the molecule.
  • the amount of monohydric alcohol or epoxy-functional silane present is from 5 % by weight to 30 %. by weight of the additive.
  • Monohydric alcohols useful in the invention contain between 8 to 18 carbon atoms, and preferably 12 to 18 carbon atoms.
  • Examples of useful monohydric alcohols include cetylalcohol, tridecyl alcohol, tetradecyl alcohol, pentadecanol, hexadecanol, heptadecanol, and octadecanol, more preferably dodecylalcohol. Numerous additional monohydric alcohols may be used in the present invention.
  • suitable epoxy-functional silanes include but are not limited to (3- glycidoxypropyi) trimethoxysilane, (3-glycidoxypropyl) triethoxysilane, (3- glycidoxypropyl) tripropoxysilane, (3-glycidoxypropyl) dimethoxymethylsilane, (3- glycidoxypropyl) dimethylmethoxysilane.
  • Other epoxy-functional silanes are known in the literature and are obtainable by procedures recognized in the art.
  • the coating composition of the present invention can also contain one or more dyes or pigments to provide color and/or hiding.
  • any conventional pigment known to those skilled in the art may be utilized, including inorganic pigments such as titanium dioxide, talc, mica, iron oxides, lead oxides, chromium oxides, lead chromate and carbon black/conductive carbon black, and organic pigments such as phthalocyanine blue and phthalocyanine green, as well as a variety of other color pigments.
  • the total amount of pigment in the coating composition will be between 15 % by weight and 60 % by weight, based on total solids.
  • the specific amount of pigment may vary, but generally, the amount of pigment is such that requisite hiding is achieved at the desired film thickness and application solids.
  • the coating composition further comprises a flexibilizer to impart additional elasticity to the dried film and help prevent cracking of the film.
  • the flexibilizer may be a polyester, a soft acrylic resin having a glass transition temperature below 10°C, or preferably, a monofunctional alkane.
  • suitable monofunctional alkanes include those having an alkyl chain of C 8 -C ⁇ of functionality X, where X can be OH, NH, NH 2 or SH.
  • C12 -C-i ⁇ compounds with OH functionality such as dodecyl alcohol, tridecyl alcohol, tetradecyl alcohol, pentadecanol, hexadecanol, heptadecanol and octadecanol.
  • the flexibilizer may be the same as the monohydric alcohol utilized in the adhesion promoter additive.
  • the present coating composition may, in addition to any solvents provided by other coating components, further include a solvent component.
  • suitable solvents include aliphatic solvents; aromatic and/or alkylated aromatic solvents such as toluene, xylene, and hydrocarbon solvents; alcohols such as isopropanol; esters; ketones; glycol ethers; and glycol ether esters.
  • the coating composition of the present invention can contain other materials well known in the art of formulating surface coatings, such as, for example, surfactants, flow control agents, thixotropic agents, fillers, anti-gassing agents, organic co-solvents, additional film-forming polymers, polymeric microparticles, catalysts and other conventional additives.
  • the coating composition of the present invention may be made using techniques well known to those skilled in the art.
  • the percent by weight solids content of the coating composition preferably varies from 19 % to 73 %.
  • the coating composition of the present invention is particularly suited for the coating of plastic substrates, including but not limited to thermoplastic polyolefins, polycarbonates, polyesters, polypropylene, polyurethanes and polyamides such as Nylon, ABS (acrylonitrile butadiene styrene copolymer), SMC (sheet molding compound), and RIM (reaction injection molding) urethane, and combinations thereof.
  • thermoplastic polyolefins polycarbonates, polyesters, polypropylene, polyurethanes and polyamides
  • polyurethanes and polyamides such as Nylon, ABS (acrylonitrile butadiene styrene copolymer), SMC (sheet molding compound), and RIM (reaction injection molding) urethane, and combinations thereof.
  • Thermoplastic polyolefin substrates are preferred.
  • the present coating composition may be applied to the substrate by any conventional means including brushing, dipping, flow coating, spraying and the like but is most often applied by spraying. Conventionally known techniques and equipment for manual or automatic spraying and electrostatic spraying can be used. Although conventional application means are employed, one of the advantages of the present coating composition is that it can be deposited directly onto the surface of a plastic substrate without the need of a separate adhesion promoter, tie coat layer or corona pretreatment.
  • top coats such as conventional base coat - clear coat composites or conventional mono coat top coats can be applied to the primer coating.
  • the coating composition can be air flashed before application of top coat layer(s) or, alternatively, can be pre-baked to a cured film prior to top coat application.
  • the novel adhesion promoter additive of the present invention may be utilized as an additive in any conventional primer composition, preferably in primer compositions comprising isocyanates. It has been found that use of the adhesion promoter additive in primer compositions provides primers having good adhesion, not only to plastic substrates but also to metal substrates, such as steel substrates.
  • adhesion promoter additives according to the present invention were prepared.
  • the first adhesion promoter additive (“APA-1") was prepared by adding, in order, 30 parts by weight dodecylalcohol, 20 parts by weight CP 343-1, a chlorinated polyolefin adhesion promoter (25 wt % CPO in xylene) available commercially from Eastman Chemicals Company, and 50 parts by weight xylene to a suitable vessel and mixing under low agitation for 15 minutes.
  • the second adhesion promoter additive (“APA-2") was prepared by adding, in order, 20 parts by weight of CP-440-1 , a non-chlorinated polyolefin adhesion promoter (25 wt % in xylene) available commercially from Eastman Chemicals Company, 75 parts by weight xylene, and 5 parts by weight of (3-glycidoxypropyl) trimethoxysilane to a suitable vessel and mixing under low agitation for 15 minutes.
  • Two control systems were utilized in examples 1 and 2 for comparison purposes.
  • Control system A is Primer PO, a CPO tiecoat composition commercially available from Akzo Nobel Coatings Inc. of Norcross, Georgia, USA.
  • Control system B is Plastoflex, a primer composition, also available commercially from Akzo Nobel Coatings Inc.
  • the plastic panel substrates used in the following examples are Hifax CA186AC, a thermoplastic olefin (TPO) available commercially from Basell Polyolefins of Elkton, Maryland, USA; Xenoy 1102, a polycarbonate (PC)/polybutylene terephthalate(PBT)blend available commercially from General Electric Plastics of Pittsfield, Massachusetts, USA, and Phase Alpha Sheet Molding Compound (SMC) available commercially from Ashland Chemical Company in Dublin, Ohio.
  • TPO thermoplastic olefin
  • PC polycarbonate
  • PBT polybutylene terephthalate
  • SMC Phase Alpha Sheet Molding Compound
  • a coating composition was prepared by adding, in order, 100 parts by volume of Colorbuild Primer, available commercially from Akzo Nobel Coatings Inc., 50 parts by volume of Colorbuild Sealer Hardener, also available commercially from Akzo Nobel Coatings, and 30 parts by volume of APA-1. These components were mixed together until homogenous and having a viscosity of 15-18 seconds on a #4DIN cup. This coating composition was then spray applied, separately, with a HPLV spray gun to each of the plastic panel substrates. The applied coating was allowed to flash for 15 minutes.
  • Control A was supplied ready to spray and was applied to the plastic panel substrates and was flashed for 15 minutes.
  • Control B was applied to the substrates as directed on the technical data sheet supplied with Control B and allowed to flash for 15 minutes. After flashing, Autobase Plus base coat and Autoclear III clear coat were applied as set forth above to all of the Control A and Control B panels.
  • a coating composition was prepared by adding 33 parts by weight of a polyester polyol with T g less than 20°C to 67 parts by weight of Colorbuild Primer and mixed with a spatula to form a modified Colorbuild Primer. 50 parts by volume of Colorbuild Sealer Hardener and 30 parts by volume of APA-2 were added to 100 parts by volume of the modified Colorbuild Primer. These components were mixed together until homogenous and having a viscosity of 15-18 seconds on a #4DIN cup. This coating composition was then spray applied, separately, with a HPLV spray gun to each of the plastic panel substrates. The applied coating was allowed to flash for 15 minutes.
  • Control A was supplied ready to spray and was applied to the plastic panel substrates and was flashed for 15 minutes.
  • Control B was applied to the substrates as directed on the technical data sheet supplied with Control B and allowed to flash for 15 minutes. After flashing, Autobase Plus base coat and Autoclear III clear coat were applied as set forth above to all of the Control A and Control B panels.
  • Humidity resistance testing according to General Motors Method 4465P and chip resistance testing according to General Motors Method 9508 were performed on the TPO panels prepared as for Sample A and Sample B above. All panels were allowed to age for seven days at ambient temperature. Mandrel Bend testing according to General Motors Method 9503P at both ambient temperature and at - 20°F was also conducted on the panels. The results are shown in Table 3 below. As can be seen in Table 3, the coatings comprising APA-1 and APA-2 had good retention and chip resistance.
  • a coating composition of the present invention was compared to currently available plastic primers.
  • the plastic panel substrates used in this example are Hifax CA186AC, a thermoplastic olefin (TPO) available commercially from Basell Polyolefins of Elkton, Maryland, USA and Cyclolac AR4051, an acrylonitrile butadiene styrene (ABS) available commercially from General Electric Plastics of Pittsfield, Massachusetts, USA,
  • a coating composition was prepared using APA-1 as for Example 1 above. This composition is hereto referred as Sample C. Sample C was compared against SUA 4903 and DPX 801 , two primers available commercially from PPG Industries, and UPO7226, a primer available commercially from The Sherwin-Williams Company.
  • Sample C was spray applied, separately, with a HPLV spray gun to the plastic panel substrates.
  • the applied coating was allowed to flash for 15 minutes.
  • Autobase Plus was activated according the technical method required for use on plastic to hiding as denoted by coverage using black and white hiding sticker.
  • the applied base coat was allowed to flash for 15 minutes until dry to a finger touch.
  • Autoclear III was activated per the technical data sheet for coating on plastics then spray applied to each of the base coats.
  • the comparative primers were applied to the substrates as directed on the technical data sheets supplied with the products. Autobase Plus base coat and Autoclear III clear coat were then applied as set forth above to all of the substrates coated with the comparative primers.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Paints Or Removers (AREA)
  • Application Of Or Painting With Fluid Materials (AREA)
  • Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
PCT/EP2005/052569 2004-06-05 2005-06-03 Adhesion promoter for plastics Ceased WO2005121259A2 (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
JP2007513967A JP2008501813A (ja) 2004-06-05 2005-06-03 プラスチック用接着促進剤
EP20050752644 EP1756235A2 (en) 2004-06-05 2005-06-03 Adhesion promoter for plastics
AU2005252376A AU2005252376A1 (en) 2004-06-05 2005-06-03 Adhesion promoter for plastics
CA 2568853 CA2568853A1 (en) 2004-06-05 2005-06-03 Adhesion promoter for plastics
BRPI0511821-2A BRPI0511821A (pt) 2004-06-05 2005-06-03 promotor de adesão para plásticos
KR1020067027554A KR20070034531A (ko) 2004-06-05 2005-06-03 플라스틱 용 부착 촉진제
MXPA06014177A MXPA06014177A (es) 2004-06-05 2005-06-03 Promotor de adhesion para plastico.

Applications Claiming Priority (2)

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US57730704P 2004-06-05 2004-06-05
US60/577,307 2004-06-05

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EP (1) EP1756235A2 (enExample)
JP (1) JP2008501813A (enExample)
KR (1) KR20070034531A (enExample)
CN (1) CN1981002A (enExample)
AU (1) AU2005252376A1 (enExample)
BR (1) BRPI0511821A (enExample)
CA (1) CA2568853A1 (enExample)
MX (1) MXPA06014177A (enExample)
RU (1) RU2006146066A (enExample)
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CN107033808B (zh) * 2010-05-10 2020-01-17 陶氏环球技术有限责任公司 助粘剂及其制备方法
PL3071648T3 (pl) * 2013-11-20 2019-07-31 Basf Se Termoplastyczne spienione wyroby poliuretanowe zawierające termoplastyczną kompozycję poliuretanową i kopolimer styrenowo-akrylowy z epoksydowymi grupami funkcyjnymi
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KR20070034531A (ko) 2007-03-28
JP2008501813A (ja) 2008-01-24
US20050271882A1 (en) 2005-12-08
WO2005121259A3 (en) 2006-04-13
CA2568853A1 (en) 2005-12-22
CN1981002A (zh) 2007-06-13
BRPI0511821A (pt) 2007-12-26
MXPA06014177A (es) 2007-01-31
EP1756235A2 (en) 2007-02-28

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