EP2493997A1 - Adhésif pour stratifiés contenant une réticulation silane - Google Patents

Adhésif pour stratifiés contenant une réticulation silane

Info

Publication number
EP2493997A1
EP2493997A1 EP10757090A EP10757090A EP2493997A1 EP 2493997 A1 EP2493997 A1 EP 2493997A1 EP 10757090 A EP10757090 A EP 10757090A EP 10757090 A EP10757090 A EP 10757090A EP 2493997 A1 EP2493997 A1 EP 2493997A1
Authority
EP
European Patent Office
Prior art keywords
groups
adhesive
silane
adhesive according
reactive
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.)
Withdrawn
Application number
EP10757090A
Other languages
German (de)
English (en)
Inventor
Lars Zander
Pavel Gentschev
Hans-Georg Kinzelmann
Svenja STRÜMPF
Nicole Ditges
Johann Klein
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.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
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 Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of EP2493997A1 publication Critical patent/EP2493997A1/fr
Withdrawn legal-status Critical Current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
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J201/00—Adhesives based on unspecified macromolecular compounds
    • C09J201/02—Adhesives based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
    • C09J201/10—Adhesives based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups containing hydrolysable silane groups
    • 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
    • C08G18/08—Processes
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • 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
    • C08G18/08—Processes
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
    • 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
    • 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
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4825—Polyethers containing two hydroxy groups
    • 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
    • C08G18/40—High-molecular-weight compounds
    • C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
    • 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
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/71—Monoisocyanates or monoisothiocyanates
    • C08G18/718—Monoisocyanates or monoisothiocyanates containing silicon
    • 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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
    • C08G65/336—Polymers modified by chemical after-treatment with organic compounds 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
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/12—Bonding of a preformed macromolecular material to the same or other solid material such as metal, glass, leather, e.g. using adhesives
    • C08J5/124—Bonding of a preformed macromolecular material to the same or other solid material such as metal, glass, leather, e.g. using adhesives using adhesives based on a macromolecular component
    • C08J5/128—Adhesives without diluent
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or 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 of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04—Homopolymers or copolymers of esters
    • C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
    • 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
    • C09J133/00—Adhesives based on homopolymers or 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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C09J133/10—Homopolymers or copolymers of methacrylic acid esters
    • C09J133/12—Homopolymers or copolymers of methyl methacrylate
    • 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
    • C09J143/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing boron, silicon, phosphorus, selenium, tellurium, or a metal; Adhesives based on derivatives of such polymers
    • C09J143/04—Homopolymers or copolymers of monomers containing silicon
    • 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
    • C09J163/00—Adhesives based on epoxy resins; Adhesives 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
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J171/00—Adhesives based on polyethers obtained by reactions forming an ether link in the main chain; Adhesives based on derivatives of such polymers
    • C09J171/02—Polyalkylene oxides
    • 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
    • C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
    • C09J175/04—Polyurethanes
    • 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
    • C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
    • 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
    • C08G2650/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G2650/28—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type
    • C08G2650/36—Pre-polymer
    • 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
    • C08J2333/00—Characterised by the use of homopolymers or 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 of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
    • C08J2333/04—Characterised by the use of homopolymers or 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 of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters
    • C08J2333/06—Characterised by the use of homopolymers or 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 of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters of esters containing only carbon, hydrogen, and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C08J2333/10—Homopolymers or copolymers of methacrylic acid esters
    • C08J2333/12—Homopolymers or copolymers of methyl methacrylate
    • 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
    • C08J2371/00—Characterised by the use of polyethers obtained by reactions forming an ether link in the main chain; Derivatives of such polymers
    • C08J2371/02—Polyalkylene oxides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L43/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing boron, silicon, phosphorus, selenium, tellurium or a metal; Compositions of derivatives of such polymers
    • C08L43/04—Homopolymers or copolymers of monomers containing silicon
    • 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
    • Y10T428/24—Structurally defined web or sheet [e.g., overall dimension, etc.]
    • Y10T428/24802—Discontinuous or differential coating, impregnation or bond [e.g., artwork, printing, retouched photograph, etc.]
    • 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
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    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/28—Web or sheet containing structurally defined element or component and having an adhesive outermost layer
    • Y10T428/2804—Next to metal
    • 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
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    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/28—Web or sheet containing structurally defined element or component and having an adhesive outermost layer
    • Y10T428/2848—Three or more layers
    • 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
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    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/28—Web or sheet containing structurally defined element or component and having an adhesive outermost layer
    • Y10T428/2852—Adhesive compositions
    • Y10T428/2878—Adhesive compositions including addition polymer from unsaturated monomer
    • Y10T428/2891—Adhesive compositions including addition polymer from unsaturated monomer including addition polymer from alpha-beta unsaturated carboxylic acid [e.g., acrylic acid, methacrylic acid, etc.] Or derivative thereof

Definitions

  • the invention relates to flowable one-component adhesives based on silane-functionalized prepolymers. These should be transparent and able to cure bubble-free. Furthermore, the invention relates to multilayer films which have as a laminating adhesive layer a crosslinked adhesive based on these silane-functionalized prepolymers.
  • Moisture-curing elastic adhesives and sealants are widely used in industry. It is desired that these bonds can be carried out on different substrates, without necessarily a pretreatment by a primer or by physical methods, such as corona treatment or plasma treatment, must be performed.
  • Such adhesives and sealants based on reactive polyurethane prepolymers are known. These often contain due to the production of even low levels of monomeric isocyanates. But that is health concern.
  • PU-based adhesives do not meet the requirements for color stability upon exposure to light. Furthermore, bubbles form in the adhesive layer at high air humidity due to the isocyanate groups.
  • Laminating adhesives are used for bonding flexible substrates, for example for films made of plastic or metal, papers or fiber materials. These should give good adhesion to the substrate, furthermore, it is necessary that the adhesives can be applied in thin layers. It should be ensured a rapid bonding, that as direct as possible further processing without long waiting times is possible. The cohesion of the adhesives should therefore be high even before crosslinking.
  • Sealant compositions are known which comprise a polymer backbone based on polymers of different composition which additionally contain moisture crosslinkable silane groups. For example, US Pat. No.
  • 4,222,925 describes a sealant comprising a mixture of a polyurethane prepolymer containing alkoxysilane groups at the chain and small amounts of .gamma.-aminopropyltrimethoxysilane. An application for bonding flexible films is not described.
  • DE 10237271 describes polymer compositions which contain alkoxysilane-terminated polymers. Furthermore, as catalysts, acids, bases, organic metal compounds or organic amino compounds may be included. Furthermore, plasticizers or fillers may be present in the polymer composition.
  • the polymers listed include polyolefins, polyacrylates, polyesters, polyethers or polyurethanes, without describing them in detail.
  • EP 1303569 describes polymers which carry at least two SiOR groups on a polymer backbone.
  • polymer backbone polyolefins polyacrylates, polyesters, polyethers, polyurethanes and other types are listed, without describing their parameters.
  • the binders can be used in adhesives, paints or foam precursors. A detailed description of the adhesives is not given.
  • DE 102006059473 is known. This describes one-component adhesives and sealants which consist of a silane-functional polyoxyalkylene prepolymer and a silane-functional polyolefin. Various additives are added to this composition, for example non-polar plasticizers, as well as the known tackifying resins.
  • Laminating adhesives according to the known prior art have the disadvantage that frequently the mechanical properties are insufficient. A quick construction of the bond is not given. Furthermore, they should have a low viscosity in order to be able to be applied in a thin layer thickness. A good elasticity Frequency is often not given, especially when a high crosslink density of the sealant is obtained. When such polyurethane-based adhesives are prepared, rapid crosslinking is possible, but the need for fast-reacting NCO groups causes increased bubbles in the adhesive film. Furthermore, such adhesives are often not clear and colorless.
  • the adhesive layer should give a fast cohesive connection of the substrates. Another object of the present invention is that these adhesives can be applied to the various substrates without primers and give good adhesion to the substrates.
  • the object is achieved by providing a one-component moisture-curing laminating adhesive comprising at least one polyoxyalkylene and / or poly (meth) acrylate prepolymer having at least one hydrolyzable silane group, at least one filler, auxiliaries and / or additives, wherein the prepolymer is a Molecular weight of 4000 to 40,000 g / mol and the adhesive has a viscosity of 2000 to 100000 mPas.
  • the 1K adhesive according to the invention may contain a polyoxyalkylene prepolymer having at least one hydrolyzable silane group.
  • These prepolymers may in principle be linear or branched and also have a plurality of silane groups. However, it is preferred if these silane groups are terminal to the polymer chain.
  • Such silane-containing prepolymers based on polyethers can be prepared in various ways.
  • the polymer backbone is based on polyoxyalkylene chains.
  • the chains can carry functional groups at the chain ends, which are then to silane groups.
  • polyether polyols are suitable as the starting polymer.
  • polyols for the prepolymers according to the invention with silane groups for example, polyoxyalkylene polyols are used. These may be the known polyether polyols based on polyethylene oxide, polypropylene oxide or polyTHF, it also being possible to use mixtures with different building blocks. Particularly suitable are di- or trifunctional polyether polyols based on polypropylene glycol. Such polyols are known to the person skilled in the art. According to the invention, it is likewise possible to use mixtures of a plurality of polyether polyols having different molecular weights. Such polyols can be functionalized singly or as a mixture with silane groups.
  • hydroxyl-functional polyethers with unsaturated chlorine compounds for example allyl chloride
  • polyethers having terminal olefinic double bonds which in turn have hydrosilane compounds which have hydrolyzable groups, such as HSi (OCH 3 ) 3 in a hydrosilylation reaction under the catalytic Influence of example transition metal compounds of Group 8 to silane-terminated polyethers are implemented.
  • polyethers containing olefinically unsaturated groups are reacted with a mercaptosilane, e.g. 3-mercaptopropyltrialkoxysilane reacted.
  • a mercaptosilane e.g. 3-mercaptopropyltrialkoxysilane
  • OH-containing polyethers are reacted with diisocyanates or polyisocyanates in excess, which are then reacted with amino-functional, hydroxy-functional or mercapto-functional silanes to form silane-terminated prepolymers.
  • isocyanates are the known aliphatic or aromatic diisocyanates, such as 1,6-hexamethylene diisocyanate (HDI), 1-isocyanato-3,3,5-trimethyl-5-isocyanatomethylcyclohexane (IPDI), xylylene diisocyanate (XDI (), tetramethylxylylene diisocyanate TMXDI), 2,4- or 2,6-tolylene diisocyanate (TDI), 2,4'-diphenylmethane diisocyanate, 2,2 '- diphenylmethane diisocyanate or 4,4-diphenylmethane diisocyanate (MDI) as well as their isomeric niche.
  • the amount is chosen so that an NCO-terminated prepolymer is obtained.
  • reaction products are then further reacted with silanes having hydrolyzable groups and an NCO-reactive group.
  • Another possibility provides for the reaction of hydroxy-functional polyethers with isocyanato-functional silanes. Selection of silanes, methods and reaction conditions are known to those skilled in the art.
  • hydroxy-functional polyethers are used by reaction to form silane-terminated prepolymers
  • a preferred embodiment uses polyether polyols which are prepared by way of DMC catalysis. These are characterized by a narrow polydispersity, in addition, the proportion of non-difunctional compounds is low.
  • laminating adhesive uses a prepolymer based on polyacrylates, which should likewise have at least one hydrolyzable silane group on the polymer chain.
  • polyacrylate polymers are also to be understood as meaning methacrylate polymers and copolymers. It is also possible to use mixed block copolymers of polyethers and polyacrylates.
  • the poly (meth) acrylates which are suitable according to the invention are polymerization products of one or more alkyl (meth) acrylate esters having 1 to 12 C atoms in the alcohol radical.
  • small amounts of (meth) acrylic acid or other copolymerizable monomers, such as styrene, vinyl esters, acrylamides may be included.
  • C to Cs - (meth) acrylate esters are suitable.
  • Such polymers are known to the person skilled in the art and can be prepared in various ways. They are also commercially available in various chemical compositions.
  • Acrylate copolymers which are suitable according to the invention should have at least two, preferably between 2 and 5, hydrolyzable silane groups. These silane groups are the above-mentioned silane groups having hydrolyzable groups. In particular, di- or tri-alkoxysilane groups are also preferred in this case with d- to C-alkoxy.
  • the silanes can be bonded to the polymer backbone via various methods of preparation. For example, it is possible to copolymerize silanes containing an unsaturated group and hydrolyzable groups. In this case, the silane groups are then randomly distributed over the polymer chain.
  • Another mode of operation is to produce acrylate polymers with unsaturated groups, with the unsaturated double bonds thereafter reacted with silanes. In this case, it is also possible to obtain such unsaturated groups and thus the silane groups terminal on the acrylate copolymer.
  • OH-group-containing acrylate polymers are prepared. These can then be reacted directly with isocyanato-silanes, or they are reacted with an excess of diisocyanates, wherein the unreacted isocyanate groups are then reacted with silanes which additionally contain a nucleophilic group.
  • Another embodiment of the invention employs acrylate block copolymers having hydrolyzable silane groups. These are preferably in the outer acrylate blocks. Such polymers are described for example in DE 10 2008 002 016. Poly (meth) acrylate copolymers having one or more reactive silane groups are also commercially available.
  • the molecular weight (number average molecular weight, M N , determinable via GPC) of the (meth) acrylate or polyether polymers is between 2000 and 75,000 g / mol. Further particularly preferred molecular weight ranges are 4000 to 50,000 g / mol, very particularly preferably up to 40,000 g / mol. These molecular weights are particularly advantageous because they allow good processability. Very particular preference is given to using polymers which have a polydispersity D (measured as M W / M N ) of less than 3, preferably less than 2, in particular less than 1.5.
  • the processing viscosity can be adjusted by adding reactive diluents or plasticizers, thus producing a composition having the desired properties.
  • silane-containing polymers based on polyethers or poly (meth) acrylates individually, with different composition or molecular weight also in a mixture. It is also important to ensure the compatibility of the polymers.
  • the compatibility can be influenced by the polymers themselves, for example, acrylates having proportions of relatively long-chain alkyl acrylates as the monomer constituent increasingly reinforced non-polar properties.
  • silane-reactive polyethers are preferred as binders.
  • the reactive silane group should contain hydrolyzable radicals.
  • R 3 C 1 to C 6 alkyl
  • Ci to C-alcohol residues or C 2 and C 3 -carboxylic acid residues as R are preferred.
  • These radicals may be present either alone or mixed on the silicon atom.
  • the number of these hydrolyzable radicals should be one to three, in particular two or three.
  • tri- or dialkoxysilane groups having methoxy, ethoxy, propoxy or butoxy groups are suitable. It is also possible to additionally contain 0, 1 or 2 alkyl groups on the silicon atom, in particular methyl, ethyl, propyl or butyl groups.
  • the reactive silane group is covalently bonded to the polymer chain. It may, for example, be bonded through an alkylene group, but it is also possible that there is a bond via heteroatoms. For example, this can be done via nitrogen, sulfur or oxygen atoms. It is also possible that other heteroatoms are present in the vicinity of the silane groups, these may influence the reactivity of the silane group.
  • the silane group can be introduced as indicated above by various methods in the preparation of the polyether prepolymers.
  • OH-functional polyethers are reacted with an excess of diisocyanates to give terminally NCO-functionalized prepolymers, which are then reacted with known silane compounds, these compounds containing at least one silane group and another nucleophilic functional group, which is reactive with an isocyanate group.
  • known silane compounds these compounds containing at least one silane group and another nucleophilic functional group, which is reactive with an isocyanate group.
  • two or three silane groups are included in this compound.
  • the molecular weight of this reactive compound should be below 1000 g / mol, in particular below 500 g / mol.
  • the nucleophilic group may be, for example, terminal to the alkyl group or this is ⁇ -permanently to the silane.
  • Examples of nucleophilic substituent-containing silanes are 3-mercaptopropyltrimethoxysilane, 3-aminopropyltrimethoxysilane, N- (2-aminoethyl) -3-aminopropyltrimethoxysilane or N- (2-aminoethyl) -3-aminopropylmethyldiethoxysilane, corresponding ethoxy- or propoxy-silanes and analogous alkyl, for example methyl, ethyl, butyl, dialkoxysilanes.
  • Beispie- Silanes containing NCO groups are trimethoxysilylpropyl isocyanate, trimethoxysilylpentyl isocyanate, Tmethoxysilylbutylisocyanat and corresponding ethoxy or propoxy silanes, or analogous methyl dialkoxy-substituted silanes. Silanes with mixed alkoxy groups are also suitable.
  • silane compounds having hydrolyzable groups which additionally contain an NCO group employs silane compounds having hydrolyzable groups which additionally contain an NCO group.
  • examples of these are isocyanatoalkyltrialkoxysilanes or isocyanatoalkyldialkoxysilanes, where in particular methoxy, ethoxy or propoxy groups may be present.
  • the number of silane groups must be at least one per polymer chain, but it may also contain up to ten silane groups. On average, about 1.5 to about 3 silane groups should be present. In a particular embodiment, an average of two silane groups are present terminal to the polyether chain.
  • silane-reactive polyoxyalkylene prepolymers or poly (meth) acrylates are usually highly viscous at room temperature (25 ° C.).
  • the viscosity can be from 1000 to 100,000 mPas (measured according to Brookfield, EN ISO 2555).
  • Polyethers suitable according to the invention which have a corresponding number of silane groups are commercially available in different molecular weights or chain structure.
  • the 1 K laminating adhesive according to the invention must additionally contain at least one finely divided pigment or filler.
  • fillers are to be understood as meaning finely divided fillers or pigments which have a high surface area.
  • so-called nano-fillers are suitable.
  • examples of such fillers are oxides or oxide / hydroxide compounds based on Si, Ti, Zr, Ba, Ca, Mg, Fe or the like.
  • these fillers / pigments should be colorless.
  • it is advantageous if these pigments dispersed in the binders are transparent. This can be influenced by the choice of particle size.
  • the surface can be measured, for example, as a BET surface area (according to DIN 66131).
  • Finely divided pigments or fillers suitable according to the invention have a surface area of from 5 to 100 m 2 , in particular from 10 to 50 m 2 / g.
  • the amount of fillers and / or pigments should be from 1 to 30% by weight, in particular from 2 to 15% by weight.
  • a particular embodiment of the invention works with silica.
  • Such silica can either be used directly or it can be surface-treated fillers.
  • the silicas are highly dispersed. The particle diameter is chosen so that transparent coatings are formed.
  • the amount of fillers, especially the silicas, enhances the cohesion of the adhesive layer.
  • Such fillers are known to the person skilled in the art and are commercially available.
  • the adhesive according to the invention may contain auxiliaries and additives. These may be, for example, plasticizers, stabilizers, antioxidants, fillers, thinners or reactive diluents, dryers, adhesion promoters and UV stabilizers, catalysts, pigments.
  • auxiliaries and additives may be, for example, plasticizers, stabilizers, antioxidants, fillers, thinners or reactive diluents, dryers, adhesion promoters and UV stabilizers, catalysts, pigments.
  • Suitable as liquid plasticizers are, for example, white oils, naphthenic mineral oils, polypropylene, polybutene, polyisoprene oligomers, hydrogenated polyisoprene and / or polybutadiene oligomers, benzoate esters, phthalates, adipates, vegetable or animal oils and their derivatives, paraffinic hydrocarbon oils, Polypropylene glycol and polybutylene glycol, liquid polyesters, Glycerines- ter or fatty acids having preferably 8 to 36 carbon atoms.
  • Stabilizers for the purposes of this invention are to be understood as meaning antioxidants, UV stabilizers or hydrolysis stabilizers. Examples of these are the commercially available sterically hindered phenols and / or thioethers and / or substituted benzotriazoles and / or amines of the "HALS" type (Hindered Amine Light Stabilizer). It is preferred in the context of the present invention, if a UV stabilizer is used, which carries a silyl group and is reacted during crosslinking or curing in the final product. Furthermore, benzotriazoles, benzophenols, none, benzoates, acrylates, hindered phenols, phosphorus and / or sulfur. The preparation according to the invention may contain up to about 3% by weight, preferably about 2% by weight, of stabilizers.
  • Catalysts which can be used are all known compounds which can catalyze the hydrolytic cleavage of the hydrolyzable groups of the silane groups and the subsequent condensation of the Si-OH group to form siloxane groups (crosslinking reaction or adhesive crosslinking function).
  • titanates such as tetrabutyl titanate or titanium tetraacetylacetonate
  • Bismuth compounds such as bismuth tris-2-ethylhexanoate
  • Tin carboxylates such as dibutyltin dilaurate (DBTL), dibutyltin diacetate or dibutyltin diethylhexanoate
  • Tin oxides such as dibutyltin oxide and dioctyltin oxide
  • Organoaluminum compounds such as aluminum acetylacetonate
  • Chelate compounds such as zirconium tetraacetyl acetonate
  • Amine compounds or their salts with carboxylic acids such as octylamine, cyclohexylamine, benzylamine, dibutylamine, monoethanolamine, triethanolamine, diethylenetriamine, triethylenetetramine, triethylenediamine, guanidine, morpholine, N-methylmorpholine
  • One embodiment uses metal catalyst-free, another uses catalysts that do not contain heavy metals such as Sn or Pb. Preference is given to mixtures of several catalysts, in an amount of 0.01 to about 5 wt .-% based on the total weight, in particular from 0.1 to 4 wt .-%, particularly preferably 0.5 to 3 wt .-% catalyst.
  • the adhesive according to the invention may also contain adhesion promoters. These can be reactive substances that can react with the substrate surface, or they are substances that increase the tack on the substrate.
  • organofunctional silanes such as hydroxyfunctional, (meth) acryloxy-functional, mercapto-functional, amino-functional or epoxy-functional silanes. These may optionally be incorporated into the polymer network.
  • mercapto-functional silanes are 3-mercaptopropyltrimethoxysilane or 3-mercaptopropyltrimethoxysilane.
  • (meth) acryloxy-functional silanes are 3-acryloxypropyltrialkoxysilane or 3-methacryloxypropyltrialkoxysilane.
  • Examples of epoxy-functional silanes are 3-glycidyloxymethylthmethoxysilane, 3-glycidyloxymethyltriethoxysilane or 2-glycidoxyethyltrimethoxysilane.
  • Examples of aminofunctional silanes are 3-aminopropylmethyldinnethoxysilane, N- (2-aminoethyl) -3-aminopropyltrinnethoxysilane (DAMO), N, N-di (2-aminoethyl) -3-aminopropyltrimethoxysilane, N- (2-aminoethyl) -N'- (2-aminoethyl) -3-aminopropyltri-methoxysilane, bis (thethoxysilylpropyl) amine, N- (n-butyl) -3-aminopropyltriethoxysilane or mixtures thereof.
  • adhesion promoter component Such adhesion promoters are known in the literature.
  • adhesion promoters are preferably used in the binder composition in amounts of between 0.1 and 10% by weight, preferably between 0.5 and 5, particularly preferably more than 1% by weight.
  • tackifying resins such as modified or unmodified resin acids or esters, polyamines, polyaminoamides, anhydrides and anhydride-containing copolymers or polyepoxide resins in small amounts.
  • Typical tackifying resins (tackifiers), such as resin acid derivatives, are used in concentrations of between 5 and 20% by weight;
  • typical adhesion promoters, such as polyamines, polyaminoamides or resorcinol derivatives are used in the range from 0 to 10% by weight.
  • Hydrolyzable silane compounds are particularly suitable as drying agents. Examples of these are carbamatopropyltrimethoxysilane, alkyltrimethoxysilane, alkyltriethoxysilane, vinyltrimethoxysilane, phenyltrimethoxysilane, tetraethoxysilane, vinyltriethoxysilane, vinyltriacetoxysilane or isooctyltrimethoxysilane. They also cause the adhesive to have a higher crosslink density. That makes after crosslinking, products with a higher modulus or higher hardness. Thus, these properties can be specifically influenced via the quantity used.
  • auxiliaries and additives in particular catalysts, adhesion promoters; Stabilizers and / or plasticizers.
  • the sum of all components should be 100 wt .-%.
  • the adhesive of the invention can be prepared by mixing the ingredients. It is advantageous to carry out the mixing at elevated temperature, so that a more easily flowable composition is mixed. It is also possible to produce the composition continuously in an extruder. The order of addition and mixing depends on the viscosity, consistency and amount of each ingredient. The solids should be uniformly dispersed or dissolved in the liquid components. Good mixing is to ensure that no separation of individual components can occur. It may be appropriate to dry individual components, so that a high storage stability is ensured. The type of production is known in principle, the skilled person can easily determine these depending on the selection of raw materials.
  • the 1 K moisture-curing laminating adhesive according to the invention should be flowable at room temperature but have a high viscosity. According to the invention it is expedient if the adhesive at a temperature between 20 to 30 ° C. has a viscosity of 2000 to 100,000 mPas. The viscosity is influenced by the choice of prepolymers and by the amount of fillers.
  • the adhesive according to the invention It is possible to heat the adhesive according to the invention to elevated temperature, for example to 30 to 60 ° C. The viscosity is lowered, it is easier processing such as pumping or application possible. Since the adhesive according to the invention is applied in a thin layer, it is rapidly cooled after application to a lower temperature, and accordingly has again a high viscosity.
  • the embodiment according to the invention is advantageous in that the adhesive according to the invention is free of organic or inorganic solvents. This application form can be applied and bonded at high speed, since no evaporation of solvents from the applied adhesive layer is necessary.
  • the methods for producing the bonded laminates are known in principle. It is necessary to evenly apply the 1K adhesive of the invention in a thin layer.
  • the application can in principle be done by printing, spraying, knife coating or rolling, but if a higher viscosity of the adhesive is desired, it is expedient to select a roller application method.
  • the adhesive is applied at elevated temperature. This allows applying a thin layer, for example between 2 to 20 ⁇ .
  • a second film-shaped substrate is adhered to the first substrate immediately after application. This can possibly be done by increased pressure.
  • solvent-based adhesives ensure that the volatile components evaporate before bonding. Due to the increased viscosity and the high tack, a good bond between the substrates is produced immediately after production. The substrates remain non-slip glued together during further processing steps, so that further processing can be carried out immediately. The final cross-linking occurs with the moisture present on the substrates or in the environment.
  • Trialkoxysilan phenomenon or Alkyldialkoxysilan phenomenon are included, in particular of d, C2, C3 - to C 4 - alkanols;
  • Another object of the invention is the use of an adhesive according to the invention for bonding flexible substrates.
  • the known films or sheet-like substrates may for example consist of metal foils, paper webs, plastic films. These can be printed or coated. These films can either be laminated against each other, it is also possible on other substrates, such as Cardboard, cardboard or similar flexible, but in principle form inconvenience substrates are applied.
  • the surface of the substrates is processed prior to bonding. It is customary to clean off adhering loose components. Furthermore, it is possible to activate the surfaces if necessary or primers are applied to a substrate.
  • the substrates can also be coated or printed on the surface.
  • the printed surface can be coated with the adhesive, or it is glued as a second substrate surface against a coated surface. According to the invention it is advantageous if the adhesive is colorless and transparent. A possible print image should not be affected.
  • the film substrates produced according to the invention can be used for various types of packaging. These may be food packaging, medical packaging or other foil packaging. It is also possible to sterilize the substrates bonded according to the invention after the production of packaging articles. This can be done by irradiation or by exposure to temperature and humidity on the substrates.
  • the adhesive according to the invention can be applied in thin layers. It enables a fast application process, with good adhesion and cohesion and after bonding. By selecting the adhesive according to the invention, transparent adhesive layers are obtained which give colorless layers even after curing. By avoiding isocyanates or other reacting rapidly with water reactive groups can be ensured that no gas bubbles arise as defects in the bonded substrates. Silane-modified prepolymer 1
  • the resulting polymer is cooled and treated with 7.1 g of vinyltrimethoxysilane and 5.3 g of a mixture of 70 wt .-% bis (1, 2,2,6,6-pentamethyl-4-piperidyl) Sebacat and 30 wt .-% of methyl-1, 2,2,6, 6-pentamethyl-4-piperidylsebazat (Tinuvin 765).
  • the product is stored moisture-tight under a nitrogen atmosphere in a glass jar before it is further processed according to the general procedure into a curable composition.
  • the resulting polymer is cooled and treated with 7.0 g of vinyltrimethoxysilane and 5.3 g of a mixture of 70 wt .-% bis (1, 2,2,6,6-pentamethyl-4-piperidyl) Sebacat and 30 wt .-% of methyl-1, 2,2,6,6-pentamethyl-4-piperidylsebazat (Tinuvin 765).
  • the product is stored moisture-tight under a nitrogen atmosphere in a glass jar before it is further processed according to the general procedure into a curable composition. Examples: (quantity in%)
  • the ingredients are mixed and degassed.
  • the adhesive is then storage stable while avoiding moisture.
  • Comparative Experiment 1 UR6082 is a 2-component polyurethane adhesive from Henkel. Comparative Experiment 2: Example 1 without filler.
  • the adhesives bond different film substrates. These are cured at RT and the tear strength is determined at daily intervals. B i ass
  • VH (1d 2d 3dd 10d 14d) 7 ,,,,,,
  • Comparison 1 PET / AI Pre-composite - 1 .57 VT, 3.44 VT, 5.72 VT,
  • Example 1 PET / AI (precompound) - 2.36 VT, 1.50 VT, PE 1 .17 VT,
  • Example 2 PET / AI (precompound) - 1 .83 VT, on PE 1.52 VT, 1 .15 VT,
  • Example 3 PET / AI (Pre-composite) - 1 .98 VT, 1.23 VT, 0.97 VT,
  • Example 4 PET / AI (Pre-composite) - 0.93 VT, 2.23 VT, 2.16 VT,
  • Example 5 PET / AI (Pre-composite) - 0.89 VT, 2.08 VT, 2.5 VT,
  • VH composite adhesion

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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)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Materials Engineering (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Laminated Bodies (AREA)

Abstract

L'invention concerne un adhésif durcissant à l'humidité à un composant contenant au moins un prépolymère de polyoxyalkyle et/ou de poly(méth)acrylate contenant au moins un groupe silane hydrolysable, au moins une charge, ainsi que des adjuvants et des additifs. Le prépolymère présente un poids moléculaire de 4000 à 40000 g/mol et l'adhésif présente une viscosité de 200 à 10000 mPas.
EP10757090A 2009-10-30 2010-09-22 Adhésif pour stratifiés contenant une réticulation silane Withdrawn EP2493997A1 (fr)

Applications Claiming Priority (2)

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DE102009046190A DE102009046190A1 (de) 2009-10-30 2009-10-30 Kaschierklebstoff mit Silanvernetzung
PCT/EP2010/063960 WO2011051056A1 (fr) 2009-10-30 2010-09-22 Adhésif pour stratifiés contenant une réticulation silane

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KR (1) KR20120100954A (fr)
CN (1) CN102597154A (fr)
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BR112012009223A2 (pt) 2016-08-23
RU2012117612A (ru) 2013-12-10
DE102009046190A1 (de) 2011-05-05
KR20120100954A (ko) 2012-09-12
CN102597154A (zh) 2012-07-18
JP2013509463A (ja) 2013-03-14
US20120282444A1 (en) 2012-11-08

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