US20180215929A1 - Primer compositions for injection molding - Google Patents

Primer compositions for injection molding Download PDF

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US20180215929A1
US20180215929A1 US15/938,547 US201815938547A US2018215929A1 US 20180215929 A1 US20180215929 A1 US 20180215929A1 US 201815938547 A US201815938547 A US 201815938547A US 2018215929 A1 US2018215929 A1 US 2018215929A1
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Prior art keywords
polystyrene
ethylene
butylene
styrene
poly
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Inventor
Brian Deegan
Darren Nolan
Brendan Kneafsey
Mark Loane
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Henkel AG and Co KGaA
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Henkel IP and Holding GmbH
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Assigned to Henkel IP & Holding GmbH reassignment Henkel IP & Holding GmbH ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: HENKEL IRELAND OPERATIONS AND RESEARCH LIMITED
Assigned to HENKEL IRELAND OPERATIONS AND RESEARCH LIMITED reassignment HENKEL IRELAND OPERATIONS AND RESEARCH LIMITED ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: DEEGAN, Brian, KNEAFSEY, BRENDAN, LOANE, MARK, NOLAN, DARREN
Priority to US16/922,065 priority Critical patent/US11697740B2/en
Assigned to HENKEL AG & CO. KGAA reassignment HENKEL AG & CO. KGAA ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: Henkel IP & Holding GmbH
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    • 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
    • C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
    • C08F212/02—Monomers containing only one unsaturated aliphatic radical
    • C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
    • C08F212/06—Hydrocarbons
    • C08F212/08—Styrene
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C45/00—Injection moulding, i.e. forcing the required volume of moulding material through a nozzle into a closed mould; Apparatus therefor
    • B29C45/0001—Injection moulding, i.e. forcing the required volume of moulding material through a nozzle into a closed mould; Apparatus therefor characterised by the choice of material
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C45/00—Injection moulding, i.e. forcing the required volume of moulding material through a nozzle into a closed mould; Apparatus therefor
    • B29C45/14—Injection moulding, i.e. forcing the required volume of moulding material through a nozzle into a closed mould; Apparatus therefor incorporating preformed parts or layers, e.g. injection moulding around inserts or for coating articles
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C45/00—Injection moulding, i.e. forcing the required volume of moulding material through a nozzle into a closed mould; Apparatus therefor
    • B29C45/14—Injection moulding, i.e. forcing the required volume of moulding material through a nozzle into a closed mould; Apparatus therefor incorporating preformed parts or layers, e.g. injection moulding around inserts or for coating articles
    • B29C45/14311—Injection moulding, i.e. forcing the required volume of moulding material through a nozzle into a closed mould; Apparatus therefor incorporating preformed parts or layers, e.g. injection moulding around inserts or for coating articles using means for bonding the coating to the articles
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C45/00—Injection moulding, i.e. forcing the required volume of moulding material through a nozzle into a closed mould; Apparatus therefor
    • B29C45/17—Component parts, details or accessories; Auxiliary operations
    • B29C45/72—Heating or cooling
    • B29C45/7207—Heating or cooling of the moulded articles
    • 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
    • C08F2/00—Processes of polymerisation
    • C08F2/46—Polymerisation initiated by wave energy or particle radiation
    • C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • 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
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/04—Acids; Metal salts or ammonium salts thereof
    • C08F220/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
    • 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
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
    • C08F220/281—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing only one oxygen, e.g. furfuryl (meth)acrylate or 2-methoxyethyl (meth)acrylate
    • 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
    • C08F285/00—Macromolecular compounds obtained by polymerising monomers on to preformed graft polymers
    • 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
    • C08F287/00—Macromolecular compounds obtained by polymerising monomers on to block 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
    • C09D153/00—Coating compositions based on block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
    • C09D153/02—Vinyl aromatic monomers and conjugated dienes
    • C09D153/025—Vinyl aromatic monomers and conjugated dienes modified
    • 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
    • C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
    • C09D4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00
    • 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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29K—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
    • B29K2023/00—Use of polyalkenes or derivatives thereof as moulding material
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29K—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
    • B29K2705/00—Use of metals, their alloys or their compounds, for preformed parts, e.g. for inserts
    • B29K2705/02—Aluminium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29K—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
    • B29K2709/00—Use of inorganic materials not provided for in groups B29K2703/00 - B29K2707/00, for preformed parts, e.g. for inserts
    • B29K2709/08—Glass
    • 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
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1811—C10or C11-(Meth)acrylate, e.g. isodecyl (meth)acrylate, isobornyl (meth)acrylate or 2-naphthyl (meth)acrylate

Definitions

  • the present invention relates to curable compositions, which may be cured by way of exposure to radiation in the electromagnetic spectrum, for use as a primer composition for injection molding applications.
  • WO 2014/193903 discloses a photocurable primer composition, comprising: a (meth)acrylate monomer component; a photoinitiator component; and a rubber component comprising a polyvinyl butyral component having a molecular weight of less than about 120,000 MW or an acrylonitrile butadiene styrene copolymer, and optionally a core shell rubber having a mean diameter in the range of about 100 to about 300 nm.
  • Bonding polyolefinic plastics to substrates can be accomplished by conventional adhesives such as wet adhesives (e.g. 2K acrylics) or PSA tapes. Such methods can be employed when bringing two pre-formed substrates together such as a polyolefin castings to a metal surface in car bumper assemblies.
  • Polyolefins are perceived as “difficult to bond” substrates, in part due to their low surface energy, and in part due to their being non-polar, non-porous and to a great extent chemically inert. Accordingly, a need also exists for alternative compositions that can bond polyolefins to other substrates for example metal or glass substrates.
  • the present invention provides a curable primer composition comprising:
  • Component (c) is a copolymer, and thus a composition where A does not differ from S, such as when the S-A-S material is polystyrene (i.e. S and A are each polystyrene), is not within the present invention.
  • composition of the invention includes materials that are of the formula S-A-S.
  • the present invention provides a curable composition
  • the polymer material is selected from block polymers represented by S-A-S where S is polystyrene and A stands for a polymer or copolymer formed from one or more of ethylene, propylene, butylene and styrene which are optionally substituted with carboxylic acid or maleic anhydride, provided that when A comprises styrene then A is a copolymer of styrene with at least one of ethylene, propylene and butylene, and is optionally substituted with carboxylic acid or maleic anhydride; and any combination of said polymer materials.
  • S polystyrene
  • A stands for a polymer or copolymer formed from one or more of ethylene, propylene, butylene and styrene which are optionally substituted with carboxylic acid or maleic anhydride, provided that when A comprises styrene then A is a copolymer of styrene with at
  • the component (c) is not simply polystyrene.
  • the present invention provides a curable composition (adhesive) which can be applied to a (rigid) substrate (such as metal or glass), yielding a tack-free coating.
  • the curable composition has a specific on-part life.
  • the coated part can then be overmolded with a polyolefin material such as a polyolefinic plastic (for example polypropylene) via any suitable process, for example an injection molding process.
  • a substrate to polyolefin part This part will have a desired structural strength.
  • the compositions of the invention when cured form a bond between the polyolefin material and the substrate which is durable.
  • a bond formed using a composition of the invention has resistance to factors such as humidity, impact and tensile stress.
  • a plastic substrate can be formed whilst substantially simultaneously creating a bond to another substrate such as a rigid substrate. This circumvents the need for a pre-molded plastic part to be made and then bonded to the other substrate in two distinct steps.
  • A is formed from one or more of ethylene, propylene, butylene and styrene, provided that A is not formed from styrene alone.
  • compositions of the present invention include those where A is formed from at least two, desirably three, of ethylene, propylene, butylene and styrene.
  • the component (c) may be selected from polystyrene-poly(ethylene-propylene)-polystyrene (“SEPS”); polystyrene-poly(ethylene-butylene)-polystyrene (“SEBS”); polystyrene-poly(ethylene-butylene-styrene)-polystyrene (“S(EBS)S”); and combinations thereof.
  • SEPS polystyrene-poly(ethylene-propylene)-polystyrene
  • SEBS polystyrene-poly(ethylene-butylene)-polystyrene
  • S(EBS)S polystyrene-poly(ethylene-butylene-styrene)-polystyrene
  • component (c) polymer comprises from about 10 to about 70 weight percent of styrene based on the total weight of polymer.
  • the component (c) polymer may comprise from about 15 to about 60 weight percent of styrene based on the total weight of polymer.
  • the component (c) may comprise from about 20 to about 60 weight percent of styrene based on the total weight of polymer.
  • These materials are of particular interest in the present invention as they confer good bond strength between a polyolefin that is subsequently overmolded and a substrate such as a metal substrate.
  • A may be substituted with carboxylic acid groups and/or maleic anhydride groups. Those substituted with maleic anhydride groups may be of particular interest.
  • the material S-A-S is at least one of polystyrene-poly(ethylene-butylene)-polystyrene (“SEBS”); and polystyrene-poly(ethylene-butylene-styrene)-polystyrene (“S(EBS)S”). These materials may be optionally substituted with carboxylic acid groups and/or maleic anhydride groups.
  • any or each carboxylic acid may be formed from maleic anhydride, for example by hydrolysis.
  • the carboxylic acid may be saturated or unsaturated.
  • the carboxylic acid may be a C 1 to C 10 carboxylic acid for example a C 4 carboxylic acid.
  • A should have no unsaturated carbon-carbon bonds.
  • compositions of the invention give better bonding performance.
  • compositions include materials, where the S-A-S is at least one of: polystyrene-poly(ethylene-propylene)-polystyrene (“SEPS”); polystyrene-poly(ethylene-butylene)-polystyrene (“SEBS”); polystyrene-poly(ethylene-butylene-styrene)-polystyrene (“S(EBS)S”); and polystyrene-poly(ethylene-ethylene/propylene)-polystyrene (“SEEPS”).
  • SEPS polystyrene-poly(ethylene-propylene)-polystyrene
  • SEBS polystyrene-poly(ethylene-butylene-styrene)-polystyrene
  • SEEPS polystyrene-poly(ethylene-ethylene/propylene)-polystyrene
  • SEEPS polystyrene-poly(ethylene-
  • the materials of the invention include the following, where the material S-A-S at least one of: polystyrene-poly(ethylene-propylene)-polystyrene (“SEPS”); polystyrene-poly(ethylene-butylene)-polystyrene (“SEBS”); and polystyrene-poly(ethylene-butylene-styrene)-polystyrene (“S(EBS)S”).
  • SEPS polystyrene-poly(ethylene-propylene)-polystyrene
  • SEBS polystyrene-poly(ethylene-butylene)-polystyrene
  • S(EBS)S polystyrene-poly(ethylene-butylene-styrene)-polystyrene
  • the SEP material may be represented by:
  • PS is shorthand for polystyrene
  • Poly(ethylene-propylene) indicates a co-polymer composed of (i) ethylene units and (ii) propylene units.
  • the SEPS material may be represented by:
  • PS is shorthand for polystyrene
  • Poly(ethylene-propylene) indicates a co-polymer composed of (i) ethylene units and (ii) propylene units.
  • the SEBS material may be represented by:
  • PS is shorthand for polystyrene
  • Poly(ethylene-butylene) indicates a co-polymer composed of (i) ethylene units and (ii) butylene units.
  • the SEEPS material may be represented by:
  • PS is shorthand for polystyrene
  • Poly(ethylene-ethylene/propylene) indicates a co-polymer composed of (i) ethylene units and (ii) ethylene/propylene units.
  • n and o are integers greater than or equal to 1. In the above structures when m and n are 1, o is greater than or equal to 2.
  • Each polymer comprises from about 10 to about 70 weight percent styrene based on the total weight of polymer. Preferably the polymer comprises from about 15 to about 60 weight percent styrene based on the total weight of polymer.
  • SB polystyrene-polybutadiene
  • SBS polystyrene-polybutadiene-polystyrene
  • SIS polystyrene-polyisoprene-polystyrene
  • SIBS polystyrene-poly(isoprene-butadiene)-polystyrene
  • maleic anhydride grafted saturated S-A-S type polymers such as maleic anhydride grafted SEBS (e.g. FG1901, 6.3 MPa).
  • SEP performed well also (e.g. G1730, 2.3 MPa).
  • shore A value greater than 60 is preferred (e.g. 502T [in table] is 30% styrene, shore A of 43, and gives a bond of 4.6 MPa, similar product of H1041 [also in table] has same 30% styrene but has shore A of 84 and bond strength improved to 5.7 MPa)
  • the metal substrate to be bonded may be aluminium including aluminium clad materials including those referred to as Al-clad which are of a type with aluminium on an aluminium alloy core, or steel such as stainless steel.
  • the present invention provides a novel formulation which has excellent bonding capabilities for overmolding substrates (such as aluminium including anodised aluminium, zinc dichromate) with polyolefinic plastics (such as PP and HDPE) via a molding process such as an injection molding process.
  • substrates such as aluminium including anodised aluminium, zinc dichromate
  • polyolefinic plastics such as PP and HDPE
  • the invention provides a curable composition optionally in the form of a UV curable adhesive which when cured on-part yields a tack-free rigid coating optionally in the form of a film.
  • the coating typically has an on-part life of at least 24 hours.
  • the adhesive system desirably comprises a UV cure system with a base of acrylate monomers (e.g. THFA and IBOA).
  • a base of acrylate monomers e.g. THFA and IBOA.
  • the coated part can then be overmolded, e.g. via injection molding, with a polyolefinic plastic (e.g. PE) to yield a bonded plastic to substrate assembly.
  • a polyolefinic plastic e.g. PE
  • the invention extends to use of a composition of the invention as a primer on a substrate to be bonded to a thermoplastic material, for example a polyolefin material.
  • thermoplastic for example polyolefin, plastic
  • the invention also provides a substrate having coated as a layer on at least a surface thereof the cure product of a composition according to the invention wherein the cure product is in a B stage, optionally for subsequent bonding to a thermoplastic material, for example a polyolefin material.
  • a combination comprising: an article having coated as a layer on at least a surface thereof a B-staged version of the composition of the invention; and a thermoplastic, for example polyolefin, plastic in contact with the B-staged version of the composition.
  • a process for forming an injection molding about an article comprising the steps of disposing into an injection molding cavity an article about which a thermoplastic, for example polyolefin, plastic material is to be molded into a shape; and injecting into the injection molding cavity in which is disposed the article the thermoplastic, for example polyolefin, plastic material at a temperature and pressure to permit the material to flow around and about the article in the mold and maintaining the mold under a temperature and pressure appropriate to permit the thermoplastic, for example polyolefin, plastic material to solidify, where prior to disposition of the article, the article is primed with the composition of any of the foregoing aspects and exposed to radiation in the electromagnetic spectrum appropriate to cure the composition.
  • a thermoplastic for example polyolefin, plastic material
  • the polyolefin material is desirably a polyolefin-based thermoplastic material such as at least one of a polyolefin-based thermoplastic elastomer, polyethylene (PE), and polypropylene (PP).
  • a polyolefin-based thermoplastic material such as at least one of a polyolefin-based thermoplastic elastomer, polyethylene (PE), and polypropylene (PP).
  • the article may be constructed from glass and aluminium such as anodized aluminium.
  • a (meth)acrylate is the most common choice.
  • Examples include N,N-dimethyl acrylamide, phenoxy ethyl(meth)acrylate, tetrahydrofurfuryl (meth)acrylate, cyclohexyl (meth)acrylate, isobornyl (meth)acrylate, butyl (meth)acrylate, hydroxyethyl (meth)acrylate, and hydroxypropyl (meth)acrylate.
  • Additional (meth)acrylates suitable for use herein include polyfunctional (meth)acrylates, such as, but not limited to, di- or tri-functional (meth)acrylates like polyethylene glycol di(meth)acrylates, tetrahydrofuran (meth)acrylates and di(meth)acrylates, hydroxypropyl (meth)acrylate (“HPMA”), hexanediol di(meth)acrylate, trimethylol propane tri(meth)acrylate (“TMPTMA”), diethylene glycol dimethacrylate, triethylene glycol dimethacrylate (“TRIEGMA”), tetraethylene glycol dimethacrylate, dipropylene glycol dimethacrylate, di-(pentamethylene glycol) dimethacrylate, tetraethylene diglycol diacrylate, diglycerol tetramethacrylate, tetramethylene dimethacrylate, ethylene dimethacrylate, neopentyl glycol diacrylate, tri
  • SiMA silicone (meth)acrylates
  • the (meth)acrylate component is selected from one or more of N,N-dimethyl acrylamide, phenoxy ethyl(meth)acrylate, tetrahydrofurfuryl (meth)acrylate, cyclohexyl (meth)acrylate, isobornyl (meth)acrylate, butyl (meth)acrylate, hydroxyethyl (meth)acrylate, and hydroxypropyl (meth)acrylate.
  • the (meth)acrylate component should comprise from about 10% to about 90% by weight, such as about 40% to about 80% by weight, based on the total weight.
  • the material S-A-S may be present in a B stage cure product of the composition, in an amount from about 5% to about 80% based on the total weight of the composition, for example from about 30% to about 60% by weight based on the total weight of the composition.
  • the composition of the invention may be applied using a carrier such as a solvent, which, for the purposes of the weight percentages given here and in the claims is not included.
  • a solvent such as a solvent
  • the material S-A-S desirably has a Shore A hardness of 20 to 100, for example from about 60 to 100.
  • the cure initiating component may be a photoinitiator component.
  • the photoinitiator may be selected from one or more of initiators triggered by radiation in the ultraviolet region of the electromagnetic spectrum, the visible region of the electromagnetic spectrum, or both.
  • the photoinitiator may be a benzophenone or substituted benzophenone, such as, for example, an ⁇ -hydroxyketone.
  • ⁇ -hydroxyketone is 1-hydroxy-cyclohexyl-phenyl-ketone (commercially available as IRGACURE 184 from Ciba Specialty Chemicals, Inc.).
  • Other suitable ⁇ -hydroxyketones and blends thereof include: 2-hydroxy-2-methyl-1-phenyl-propan-1-one (DAROCUR 1173); 2-hydroxy-1-[4-(2-hydroxyethoxy)phenyl]-2-methyl-1-propanone (IRGACURE 2959); and blends such as IRGACURE 1000 and IRGACURE 500 (all commercially available from Ciba Specialty Chemicals, Inc.).
  • UV photoinitiators include: acetophenone and substituted acetophenones; benzoin and its alkyl esters; xanthone and substituted xanthones; diethoxy-acetophenone; benzoin methyl ether; benzoin ethyl ether; benzoin isopropyl ether; diethoxyxanthone; chloro-thioxanthone; N-methyl diethanol-amine-benzophenone; 1-benzoyl cyclohexanol; 2-benzyl-2-(dimethylamino)-1-[4-(4-morpholinyl)phenyl]-1-butanone; amino ketones, such as IRGACURE 907, IRGACURE 369 and IRGACURE 1300 (all commercially available from Ciba Specialty Chemicals, Inc.); benzildimethyl-ketals, such as IRGACURE 651 (commercially available from Ciba Specialty Chemicals, Inc.); BAPO (bis
  • U.S. Pat. No. 5,399,770 discloses and claims a class of compounds functional as such photoinitiators.
  • the disclosure of the '770 patent is hereby express incorporated herein by reference in its entirety.
  • a particularly desirable photoinitiator embraced by the 770 patent is available commercially from Ciba Specialty Chemicals under the trade name IRGACURE 819.
  • IRGACURE 819 is bis(2,4,6-trimethyl benzoyl)phenyl phosphine oxide.
  • Camphorquinone peroxyester initiators 9-fluorene carboxylic acid peroxyesters; dl-camphorquinone; IRGACURE 784DC (photoinitiator based on substituted titanocenes); two-component initiators including a dye and electron donor; three-component initiators including a dye, electron donor and oxidant; and combinations thereof, may also be used. These visible light photoinitiators may be used in conjunction with bisacyl phosphine oxide photoinitiators to achieve the desired effect.
  • suitable dyes include, but are not limited to camphorquinone, 5,7-diiodo-3-butoxy-6-fluorone, rose bengal, riboflavin, eosin Y, benzil, fluorone dyes, benzil derivatives, ketocoumarins, acridine dyes, benzoflavin and combinations thereof, and suitable electron donors include, but are not limited to methyldiethanolamine, dimethyl-p-toluidine, N,N-dimethylaminoethyl methacrylate, ethyl 4-dimethylaminobenzoate and combinations thereof.
  • suitable oxidants include, but are not limited to bis(trichloromethyl)triazines, onium salts and combinations thereof.
  • onium salts include sulfonium and iodonium salts.
  • U.S. Pat. No. 4,505,793 which is incorporated by reference herein, discloses photopolymerization initiators that include a combination of a 3-keto-substituted coumarin compound and an active halogen compound. A number of exemplary compounds are disclosed. Such photopolymerization initiators cure by exposure to light having wavelengths ranging between about 180 nm and 600 nm.
  • U.S. Pat. No. 4,258,123 which is incorporated by reference herein, discloses photosensitive resin compositions including initiator components that generate a free radical upon irradiation with actinic light. Such components include various triazine compounds, as more fully described therein.
  • EP 0 369 645 A1 discloses a three-part photoinitiator system which includes a trihalomethyl substituted-s-triazine, a sensitizing compound capable of absorbing radiation in the range of about 300-1000 nm and an electron donor.
  • Exemplary sensitizing compounds are disclosed, including: ketones; coumarin dyes; xanthene dyes; 3H-xanthen-3-one dyes; acridine dyes; thiazole dyes; thiazine dyes; oxazine dyes; azine dyes; aminoketone dyes; methane and polymethine dyes; porphyrins; aromatic polycyclic hydrocarbons; p-substituted aminostyryl ketone compounds; aminotriaryl methanes; merocyanines; squarylium dyes; and pyridinium dyes.
  • Exemplary donors also are disclosed, including: amines; amides; ethers; ureas; ferrocene; sulfinic acids and their salts; salts of ferrocyanide; ascorbic acid and its salts; dithiocarbamic acid and its salts; salts of xanthates; salts of ethylene diamine tetraacetic acid; and salts of tetraphenylboronic acid.
  • Such initiators are sensitive to both UV and visible light.
  • EP 0 563 925 A1 discloses photopolymerization initiators including a sensitizing compound that is capable of absorbing radiation in the range of about 250-1000 nm and 2-aryl-4,6-bis(trichloromethyl)-1,3,5-triazine.
  • Exemplary sensitizing compounds that are disclosed include dyes such as cyanine, merocyanine, coumarin, ketocoumarin, (thio)xanthene, acridine, thiazole, thiazine, oxazine, azine, aminoketone, squarylium, pyridinium, (thia)pyrylium, porphyrin, triaryl methane, (poly)methine, amino styryl compounds and aromatic polycyclic hydrocarbons.
  • These photopolymerization initiators are sensitive to UV and visible light.
  • U.S. Pat. No. 5,395,862 which is expressly incorporated by reference herein, discloses fluorone photoinitiators, which are sensitive to visible light. Such fluorone initiator systems also include a co-initiator, which is capable of accepting an electron from the excited fluorone species. Exemplary co-initiators are disclosed, including: onium salts, nitrohalomethanes and diazosulfones.
  • U.S. Pat. No. 5,451,343, which is incorporated herein by reference discloses fluorone and pyronin-Y derivatives as initiators that absorb light at wavelengths of greater than 350 nm.
  • 5,545,676 which is incorporated by reference herein, discloses a three-part photoinitiator system, which cures under UV or visible light.
  • the three-part system includes an arylidonium salt, a sensitizing compound and an electron donor.
  • Exemplary iodonium salts include diphenyliodonium salts.
  • 2,4,6 trimethylbenzoyldiphosphine oxide and 1-hydrocyclohexyl-phenyl ketone are two particularly desirable photoinitiators for use in the compositions.
  • the photoinitiator component should be present in an amount of about 1 to about 5 weight percent.
  • the inventive composition may be used as a primer for an article which is to be subjected to an overmolding process in which an injection molding is to be formed about the article.
  • the article may be constructed from a variety of substrates, though glass and aluminium are the preferred choices, with anodized aluminium being a particularly desirable choice.
  • the inventive composition may be applied to the article to be overmolded and then exposed to radiation in the electromagnetic spectrum in order to fix the composition on at least a portion of the surface of the article.
  • composition may be applied to the article in any of several ways, such as spraying, screen printing, touch transfer and the like. After application it is cured (or B staged) to a dry-to-the-touch (or tack free) surface by exposure to energy in the electromagnetic spectrum, such as UV or UV/visible radiation.
  • This B staging permits the primer coated article to be stored for later use in the overmolding process.
  • the primer coated article is disposed into an injection molding cavity and the cavity closed in order to receive the thermoplastic resin to be injected therein under elevated temperature and/or pressure conditions.
  • thermoplastic material e.g. resin is ordinarily chosen from polyolefin materials such as polyethylene and polypropylene.
  • the thermoplastic resin should be injected into the molding cavity at an elevated temperature and pressure; suitable to completely mold the finished assembly in 0.5-5 seconds.
  • the temperature time and pressure will depend on the particular thermoplastic as well as the size, geometry and path length of the mold cavity. Typical temperatures will be in the range of about 180° C. to 300° C., such as 260° C. and pressures of 50 to 5000 psi, such as 500 psi.
  • the flow rate must be suitable to fill the entire mold cavity before the thermoplastic reaches a no-flow state.
  • FIG. 1 An example of one or more articles that may be formed by the overmolding process so described may be seen with reference to FIG. 1 .
  • FIG. 1 An example of one or more articles that may be formed by the overmolding process so described may be seen with reference to FIG. 1 .
  • FIG. 1 An example of one or more articles that may be formed by the overmolding process so described may be seen with reference to FIG. 1 .
  • four articles may be prepared with the so-disclosed overmolding technology: 1. touch panel window 11 and cover 12 ; 2. speaker 21 and camera lens 22 ; 3. cover 31 , metal trim 32 and subframe 33 ; and 4. touch panel 41 , plastic bezel 42 and metal trim 43 .
  • FIG. 1 depicts an exploded view of various component layers of a hand held consumer electronic display device, about which overmolding may be used as the interface therebetween;
  • FIG. 2 is a graph showing the bonding results achieved with Example 4 from Table 1;
  • FIG. 3 is a graph showing the bonding results achieved with Example 7 from Table 1.
  • a polyolefin pin of diameter 12.65 to 12.675 mm and a minimum of 37.5 mm length is injection molded onto a metal or glass plate 101.6 mm ⁇ 25.4 mm and thickness from 1.0 to 5.5 mm.
  • the injection molding machine used was a Travin MINI MOULDER TP1, the barrel temperature used was 220° C., and the mold was unheated.
  • the glass or metal plate has already been provided with a cured coating of the test formulation covering the surface. This coating is a B-staged version of the composition. It has been cured with a first cure mechanism, which is UV light, but can react when subsequently contacted with the melted thermoplastic, e.g. polyolefin. The coating thus has the material from the pin molded thereon.
  • test plastic used in the results below is polypropylene (sold under the trade name) TATREN IM 25 75, and the solid substrate used in the reported data is an anodised aluminium plate 101.6 mm ⁇ 25.4 mm and thickness of 1.6 mm.
  • This pin is pulled in a tensile test 24 hours after bonding at a rate of 2.0 mm/min using a Hounsfield tensile testing machine with a calibrated 5 kN load cell attached.
  • Table 1 below is a list of additives that were tested in formulations specified in the Examples below. These compositions were applied to anodised aluminium and cured. Polypropylene was then injected moulded onto the cured films. The bond strengths measured at 24 hours post-bonding are included for each.
  • % S in polymer is the percentage of polystyrene by weight in the polymer.
  • Example 1 (from Table 1) was the following formulation (the Polymer Material is the VAMAC material):
  • Examples 2 and 5 were based on the following formulation. Only the Polymer Material differs between these Examples and the Example no.s set out in Table 1 correspond to the following formulations with the Polymer Material being that indicated in Table 1 for the respective Examples.
  • Example 3 (from Table 1) was the following formulation (the Polymer Material is the Polytail material):
  • Examples 4 and 6 to 23 were based on the following formulation. Only the Polymer Material differs between these Examples and the Example no.s set out in Table 1 correspond to the following formulations with the Polymer Material being that indicated in Table 1 for the respective Examples.
  • Example 4 A graph showing further bonding results achieved with the composition of Example 4 on various combinations of substrates is shown in FIG. 2 .
  • the injection barrel temperature was 220° C.
  • Example 7 A graph showing further bonding results achieved with the composition of Example 7 on various combinations of substrates is shown in FIG. 3 .
  • the injection barrel temperature was 220° C.
  • THFA Tetrahydrofurfuryl Acrylate
  • IBOA Isobornyl Acrylate
  • Examples 1 to 3 are comparative examples. No bond strength is achieved.
  • Examples 9, 10, 11, 22 and 23 are comparative examples. No bond strength is achieved.
  • the “B” in the acronym for the materials is used in a non-unique manner, for example in SB; SIBS; and SBS the “B” stands for a polymer based on butadiene whereas in SEBS and S(EBS)S the “B” stands for a polymer based on butylene.

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  • Health & Medical Sciences (AREA)
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  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Mechanical Engineering (AREA)
  • Manufacturing & Machinery (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Laminated Bodies (AREA)
  • Injection Moulding Of Plastics Or The Like (AREA)
  • Polymerisation Methods In General (AREA)
  • Graft Or Block Polymers (AREA)
  • Paints Or Removers (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
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CN112592445B (zh) * 2020-12-16 2023-06-09 珠海冠宇动力电池有限公司 一种粘结剂及其制备方法和在锂离子电池中的应用

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