[go: up one dir, main page]
More Web Proxy on the site http://driver.im/

EP1560859A2 - Adhesif de contact chimiquement inerte a adherence amelioree, son procede de production et son utilisation - Google Patents

Adhesif de contact chimiquement inerte a adherence amelioree, son procede de production et son utilisation

Info

Publication number
EP1560859A2
EP1560859A2 EP03810955A EP03810955A EP1560859A2 EP 1560859 A2 EP1560859 A2 EP 1560859A2 EP 03810955 A EP03810955 A EP 03810955A EP 03810955 A EP03810955 A EP 03810955A EP 1560859 A2 EP1560859 A2 EP 1560859A2
Authority
EP
European Patent Office
Prior art keywords
meth
acrylate
composition according
polymer composition
acrylates
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Withdrawn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
EP03810955A
Other languages
German (de)
English (en)
Inventor
Hansjörg Ander
Günter Holl
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.)
Lohmann GmbH and Co KG
Original Assignee
Lohmann GmbH and Co KG
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 Lohmann GmbH and Co KG filed Critical Lohmann GmbH and Co KG
Publication of EP1560859A2 publication Critical patent/EP1560859A2/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/06—Polymers provided for in subclass C08G
    • 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
    • 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
    • C08F220/14—Methyl esters, e.g. methyl (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
    • 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
    • C08F220/1802—C2-(meth)acrylate, e.g. ethyl (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
    • 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
    • C08F220/1803—C3-(meth)acrylate, e.g. (iso)propyl (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
    • 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
    • C08F220/1806—C6-(meth)acrylate, e.g. (cyclo)hexyl (meth)acrylate or phenyl (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
    • 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
    • C08F220/1808—C8-(meth)acrylate, e.g. isooctyl (meth)acrylate or 2-ethylhexyl (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
    • 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
    • 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
    • C08F220/20—Esters of polyhydric alcohols or phenols, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(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
    • 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
    • C08F220/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (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
    • C08F222/00—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 a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/10—Esters
    • C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
    • 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
    • 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
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
    • C09J7/38—Pressure-sensitive adhesives [PSA]
    • C09J7/381—Pressure-sensitive adhesives [PSA] based on macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • C09J7/385—Acrylic polymers
    • 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
    • C09J2301/00—Additional features of adhesives in the form of films or foils
    • C09J2301/30—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier
    • C09J2301/302—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier the adhesive being pressure-sensitive, i.e. tacky at temperatures inferior to 30°C

Definitions

  • the present invention relates to pressure sensitive adhesives which are resistant to chemicals and process additives and at the same time have improved adhesion to polar and semipolar substrates, in particular to glass.
  • the invention relates to the production of chemically inert pressure sensitive adhesives and their use, in particular for the production of pressure sensitive adhesive tapes with high initial tack (tack) on polar and semipolar substrates such as glass, metal, polycarbonate and similar materials.
  • the initial adhesion of a PSA tape depends on the substrate to which the PSA tape is applied.
  • substrates with polar surfaces such as glass or metal
  • a value for the initial adhesion of about 25 to 30 N / 25 mm is regarded as high.
  • substrates with non-polar surfaces such as polyethylene or polypropylene
  • values of more than 15 N / 25 mm are already considered high.
  • the currently customary pressure sensitive adhesive tapes based on pure acrylate have an initial adhesion to substrates with non-polar surfaces which is in the range between 5 and 12 N / 25 mm.
  • Pressure sensitive adhesive tapes with a high tack on polar substrates are widely used in industrial processes.
  • the pressure sensitive adhesives used for such adhesive tapes usually consist of polyacrylates or mixtures of polyacrylates with resins (tackifiers).
  • the polyacrylates are obtained by radical polymerization of mixtures of monomeric acrylates, such as, for example, esters of acrylic acid, methyl acrylic acid, ethyl acrylic acid, Butyl acrylic acid and the like, or the acids themselves.
  • the polymerization takes place in solvents by means of thermal activation or in bulk by means of activation by high-energy radiation (UV or EB curing).
  • Acrylic acid is preferably used to achieve a high initial tack.
  • the initial adhesive force comes from the interaction of the strongly polar carboxyl group of acrylic acid with the polar or semi-polar substrates (dipole-dipole interaction, hydrogen bonds).
  • the object of the invention is achieved by pressure-sensitive adhesives based on copolymers of methacrylates and acrylates.
  • the desired high tack of the pressure sensitive adhesives according to the invention is achieved by polar acrylates such as 2-hydroxyethyl acrylate, 3-hydroxypropyl acrylate, 4-hydroxybutyl acrylate, PEG acrylates, 2-aminoethyl acrylate, 3-aminopropyl acrylate, 4-aminobutyl acrylate or the preceding compounds corresponding methacrylates achieved.
  • Polar groups in the acrylates which are capable of hydrogen bonding to the substrates, are important for achieving a high level of tack. These include, in particular, hydroxyl, amino and thio groups and to a lesser extent urea, urethane and imino groups, ie generally acrylates with at least one Zerewitinoff Probe hydrogen.
  • a Zerewitinoff hydrogen is the so-called active hydrogen, which can be determined by a method found by Tschugaeff and Zerewitinoff by reaction with methylmagnesium iodide in butyl or other ethers.
  • the Zerewitinoff Probe hydrogen includes the active hydrogen bound to N, O or S. Carboxy, hydroxy, A ino and I ino as well as thiol groups, but also the active hydrogen of H-acidic hydrocarbons, which can be quantified in individual cases with the methods of Tschugaeff and Zerewitinoff.
  • polar (meth) crylates which have no carboxyl groups but are selected from the group of the hydroxy (meth) acrylates.
  • non-polar acrylates and / or methacrylates are, for example, esterification products made from acrylic acid and monohydric alcohols, and the corresponding products such as those formed when using methacrylic acid.
  • the products of the alcohols C 4-C1.5_ are preferred and the reaction products of the alcohols C 6 -C 10 are particularly preferred.
  • a crosslinker can be added to the acrylate and / or methacrylate mixtures during the polymerization.
  • the crosslinking agents are, on the one hand, acrylates or methacrylates of the di-, tri-and higher-valent alcohols or analog vinyl ethers (hereinafter also referred to as di-, tri-functional and higher (meth) acrylates) or mixtures thereof.
  • the polymers can also be crosslinked after the polymerization, including the polar acrylates, using isocyanates, epoxides, aziridines, metal complexes or other multifunctional compounds or mixtures thereof which react with Zerewitinoff hydrogen. Mixtures of (meth) acrylate-containing crosslinking agents with compounds reactive towards H-acidic compounds are of course also possible.
  • the degree and type of crosslinking in the production of the polymer composition according to the invention depends on the softness and internal strength of the adhesive polymers required for later use, as well as further characteristic values such as heat and cold resistance, tack and the like.
  • the adhesives according to the invention can be produced from:
  • the polar (meth) crylates with Zerewitinoff hydrogen according to a) are reaction products of acrylic or methacrylic acid with two-, three- or higher-functional alcohols and theirs
  • the apolar (meth) crylates according to b) are reaction products of onofunctional alcohols or amines with acrylic acid or methacrylic acid and mixtures thereof.
  • Technically important representatives of this class are methyl (meth) acrylate, ethyl acrylate, butyl acrylate, hexyl (meth) acrylate, isooctyl acrylate, 2-ethylhexyl acrylate, isodecyl (meth) acrylate, isobornyl (meth) acrylate, alkyl (meth) aerylamides.
  • monomers that are accessible to radical polymerization such as vinyl compounds, are added to the (meth) acrylate mixtures according to the invention in minor amounts, should special requirements for the adhesive polymer make this necessary.
  • (Meth) acrylate according to c) is understood to mean compounds which are formed by the reaction of polyhydric alcohols
  • the class of "higher-quality (meth) acrylate-containing compounds" in the sense of the previous definition of c) further includes the compounds from the series of (meth) acrylated polyesters and (meth) acrylated polyurethanes.
  • the (meth) acrylated polyesters are are the reaction products of OH-terminated polyester polyols, mostly of oligomeric origin, with (meth) acrylic acid or the products from the reaction of carboxyl-containing polyester polyols, also mostly in oligomeric form, with OH-group-containing (meth) acrylates
  • Polyurethanes are reaction products of amine- or hydroxyl-terminated (meth) crylates with di-, tri- or polyisocyanates (for example 1,6-hexamethylene diisocyanate, 2,4- or 2,6-tolylene diisocyanate, isophorone diisocyanate), their urea , Derivatives containing biuret or alophanate or the di- and tri
  • a compound according to c) which is reactive toward Zerewitinoffs hydrogen is understood to mean epoxides, isoeyanates, cyanates, aziridines, metal chelates or others state-of-the-art compounds which are able to form a chemical bond with CH acidic compounds.
  • An initiator according to d) is understood to mean compounds which, when exposed to thermal energy or high-energy radiation, are able to decompose into radicals and to initiate radical polymerization.
  • examples of such initiators are azo compounds, peroxide compounds, aromatic ⁇ -hydroxyketones, arylphosphorus compounds, and similar radical initiators.
  • a liquid, chemically inert medium according to e) means a liquid compound which is able to dissolve, emulsify or disperse the polymer formed.
  • These include compounds such as esters, ketones, alcohols, hydrocarbons, cycloaliphatics, aromatics, water or mixtures of these compounds.
  • the polymer compositions according to the invention can be prepared not only in organic solvents (solution polymerization) but also in water (emulsion polymerization), but also without solvents by means of UV light or electron beams.
  • the polymers according to the invention are produced and processed in a known manner.
  • the polymer is known in a liquid, chemically inert medium (component according to e)) from (meth) acrylates with Zerewitinoff hydrogen, apolar (meth) acrylates and an initiator (the components according to a), b ), d)) produced (solution polymerization).
  • This solution comes with a compound active against Zerewitinoff Hair hydrogen reacted according to c).
  • the solution can then be processed in a coating system with a downstream drying tunnel according to the prior art to form a tape-like adhesive or sealant.
  • (meth) acrylates with Zerewitinoff's hydrogen, apolar (meth) crylates and an initiator are emulsified in water.
  • additional dispersants or emulsifiers known to the person skilled in the art may be indicated here.
  • the reaction mixture is converted in a known manner to a polymer dispersion or emulsion with a solids content of between 10 and 70% by weight. This can then be processed into tape-like sealants and adhesives analogously to the solvent-based polymers.
  • a polymer syrup is produced from components a) to c) in a known manner.
  • component c) preference is given to using bifunctional, trifunctional or higher functional (meth) acrylates.
  • the polymer syrup can then be processed on a coating machine with a subsequent curing device using high-energy radiation to form tape-like adhesives and sealants.
  • the polymer composition according to the invention can be used as an adhesive or sealant.
  • the polymer composition according to the invention is preferably further processed to PSA tapes.
  • An initial adhesion of up to 50 N / 25 mm on substrates with a polar surface and up to 20 N / 25 mm on substrates with a non-polar surface was measured with the PSA tapes produced with the aid of the polymers according to the invention. Examples
  • the solution is spread out to a film 0.2 mm thick. After the solvent has been flashed off, the film is dried at 90 ° C. for 10 minutes. A pressure-sensitive adhesive film is obtained.
  • Ethylhexyl acrylate, 50 parts by weight of 2-hydroxyethyl acrylate and 50 parts by weight of acrylic acid are mixed in 450
  • the solids content of the adhesive solution is 50% by weight, the residual monomer content a maximum of 2.5% by weight. After drying, a pressure-sensitive film is obtained.
  • the adhesive films were applied to an aluminum sheet and covered with isocyanate (HDI) at the edges so that the isocyanate was in contact with both the adhesive and the aluminum substrate.
  • HDI isocyanate
  • the adhesives according to the invention are notable for high resistance to reactive substances. At the same time, the adhesion to polar substrates compared to conventional (acrylic acid-containing) adhesives is not adversely affected.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Adhesive Tapes (AREA)
  • Sealing Material Composition (AREA)

Abstract

L'invention concerne des adhésifs de contact chimiquement inertes qui présentent une adhérence améliorée sur des substrats polaires et semi-polaires. L'invention concerne également leur production et leur utilisation, notamment pour la production de rubans adhésifs à adhérence instantanée élevée sur des substrats polaires et semi-polaires.
EP03810955A 2002-11-14 2003-10-31 Adhesif de contact chimiquement inerte a adherence amelioree, son procede de production et son utilisation Withdrawn EP1560859A2 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10252978 2002-11-14
DE10252978A DE10252978A1 (de) 2002-11-14 2002-11-14 Chemisch inerter Haftkleber mit verbesserter Haftung, Verfahren zu seiner Herstellung und Verwendung
PCT/EP2003/012116 WO2004044021A2 (fr) 2002-11-14 2003-10-31 Adhesif de contact chimiquement inerte a adherence amelioree, son procede de production et son utilisation

Publications (1)

Publication Number Publication Date
EP1560859A2 true EP1560859A2 (fr) 2005-08-10

Family

ID=32240036

Family Applications (1)

Application Number Title Priority Date Filing Date
EP03810955A Withdrawn EP1560859A2 (fr) 2002-11-14 2003-10-31 Adhesif de contact chimiquement inerte a adherence amelioree, son procede de production et son utilisation

Country Status (9)

Country Link
US (1) US20060052561A1 (fr)
EP (1) EP1560859A2 (fr)
JP (1) JP2006506476A (fr)
KR (1) KR20050089003A (fr)
CN (1) CN100334121C (fr)
AU (1) AU2003301964A1 (fr)
DE (1) DE10252978A1 (fr)
TW (1) TWI289579B (fr)
WO (1) WO2004044021A2 (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102006009336B4 (de) * 2006-03-01 2008-07-10 Naomi Rechte Gmbh Anordnung eines Trennwandelementes und eines das Trennwandelement seitlich einfassenden Einfassungsmittels
CA2709652C (fr) 2009-08-07 2013-11-12 Rohm And Haas Company Calfeutrant et joints d'etancheite depourvus de plastifiant avec proprietes d'adhesion a l'etat humide ameliorees
KR20140031849A (ko) * 2010-12-13 2014-03-13 쓰리엠 이노베이티브 프로퍼티즈 컴파니 저 표면 에너지 기재용 감압 접착제
CN103396741B (zh) * 2013-07-25 2015-01-21 湖北大学 一种零voc光聚合丙烯酸酯压敏胶组合物及制备方法
WO2020100832A1 (fr) * 2018-11-15 2020-05-22 デンカ株式会社 Composition
CN111087524B (zh) * 2019-12-17 2022-11-18 苏州赛伍应用技术股份有限公司 一种聚丙烯酸酯、压敏胶黏剂、压敏胶带、软磁屏蔽片及其制备方法

Family Cites Families (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE630641A (fr) * 1962-04-19
NL300138A (fr) * 1962-11-05 1900-01-01
US3269994A (en) * 1963-09-30 1966-08-30 Catalin Corp Of America Solvent-resistant pressure-sensitive adhesive coating and method of producing the same
GB1084412A (en) * 1963-12-20 1967-09-20 Monsanto Co Improvements in and relating to adhesives
JPS5835549B2 (ja) * 1976-06-10 1983-08-03 東洋インキ製造株式会社 感圧性接着剤
DE3018131A1 (de) * 1980-05-12 1981-11-19 Basf Ag, 6700 Ludwigshafen Polyisocyanate enthaltende haftkleber
GB8331778D0 (en) * 1983-11-29 1984-01-04 Allied Colloids Ltd Pressure sensitive adhesives
JPH0651762B2 (ja) * 1987-05-19 1994-07-06 三菱油化バ−デイツシエ株式会社 粘接着剤用共重合体水性分散体の製造法
FR2624872B1 (fr) * 1987-12-22 1991-10-18 Elf Aquitaine Formulation adhesive acrylique anaerobie stable chimiquement et susceptible de fournir un joint adhesif durci presentant des resistances ameliorees au choc et au cisaillement ou/et une bonne tenue thermique
DE3926897C1 (fr) * 1989-08-16 1991-03-14 Lohmann Gmbh & Co Kg, 5450 Neuwied, De
US5326644A (en) * 1993-02-05 1994-07-05 Avery Dennison Corporation Repulpable pressure-sensitive adhesive compositions
DE19501024C2 (de) * 1995-01-14 1999-09-23 Lohmann Gmbh & Co Kg Strahlenvernetzbare, radikalisch erzeugte haftklebende Polymere auf Polyacrylatbasis und ihre Verwendung
US5646221A (en) * 1995-03-31 1997-07-08 Kowa Co., Ltd. Adhesive base material
JP2001055550A (ja) * 1999-08-20 2001-02-27 Nippon Nsc Ltd アクリル系水性粘着剤組成物
US6420102B1 (en) * 2001-07-27 2002-07-16 Eastman Kodak Company Thermally developable imaging materials containing hydroxy-containing polymeric barrier layer
US6713641B2 (en) * 2001-10-19 2004-03-30 Eastman Chemical Company Reactive anthraquinone colorant compounds and polymeric materials reacted therewith

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2004044021A2 *

Also Published As

Publication number Publication date
WO2004044021A3 (fr) 2004-12-09
KR20050089003A (ko) 2005-09-07
AU2003301964A1 (en) 2004-06-03
WO2004044021A2 (fr) 2004-05-27
TWI289579B (en) 2007-11-11
US20060052561A1 (en) 2006-03-09
JP2006506476A (ja) 2006-02-23
DE10252978A1 (de) 2004-06-03
CN1711294A (zh) 2005-12-21
TW200417574A (en) 2004-09-16
CN100334121C (zh) 2007-08-29

Similar Documents

Publication Publication Date Title
DE60307113T3 (de) STRAHLUNGSHûRTBARER, LÖSUNGSMITTELFREIER UND AUFDRUCKBARER VORGûNGER EINES HAFTKLEBEMITTELS
EP3247755B1 (fr) Dispersions aqueuses contenant des produits de polymérisation multicouches et compositions d'agent de revêtement les contenant
EP1293547B1 (fr) Procédé de préparation d'adhesifs acryliques thermofusibles par extrusion réactive
EP2087021B1 (fr) Mélange durcissable par rayonnement contenant des composés à bas poids moléculaire éthyléniquement insaturés comprenant des systèmes à noyau non aromatiques
EP1576017B2 (fr) Masse collante d'acrylate transparente comprenant une charge
EP1357140B1 (fr) Copolymères acrylates et adhésifs pouvant être obtenus à partir de ceux-ci pour le collage de surfaces à faible énergie
EP3423535B1 (fr) Dispersions aqueuses contenant des produits de polymerisation multicouches et compositions d'agent de revetement les contenant
DE102010001992A1 (de) Funktionsmaterialien mit steuerbarer Viskosität
EP2697324B1 (fr) Dispersion d'adhésif de contact contenant des polymères comportant des groupes uréido ou des groupes analogues uréido et comportant des groupes glycidyle
EP3347388B1 (fr) Masse adhésive modifiée par une résine adhésive
DE102012007823A1 (de) Polymerisate, die durch emulsionspolymerisation von funktionalisierten polyurethan-nanopartikeln und radikalisch härtbaren monomeren herstellbar sind, ein verfahren zu deren herstellung sowie deren verwendung
DE102013206376A1 (de) Schwarzer Silan-Primer zur Verbesserung der Adhäsion von Klebebändern auf Glasoberflächen
EP1297023B1 (fr) Procede de production de substances auto-adhesives d'acrylate reticulables
EP2870209B1 (fr) Laque transparente durcissant aux uv et thermiquement pour la retouche de peinture de véhicules automobiles
EP1294783B1 (fr) Procede de production de substances auto-adhesives d'acrylate reticulables
WO2015090811A1 (fr) Pâtes à pigment contenant une dispersion aqueuse d'un polymère mixte
TWI725645B (zh) 用於接合聚合物之可固化熱封黏著劑
WO2007073827A1 (fr) Adhesif structurel a elasticite accrue
EP1560859A2 (fr) Adhesif de contact chimiquement inerte a adherence amelioree, son procede de production et son utilisation
DE102019215766A1 (de) Reaktiver Klebstofffilm mit guter Feuchtwärmebeständigkeit, insbesondere zum Verkleben von Polyamid
EP0547504B1 (fr) Procédé pour souder à chaud avec un matériel de revêtement soudable à chaud
DE2357486C2 (de) Verfahren zur Herstellung selbsthaftender Überzüge
DE102013226504A1 (de) Scherfeste Haftklebemasse mit hohem Tack
DE102007021776B4 (de) Verfahren zur Herstellung anorganisch/organischer Hybridpolymere
DE2659663A1 (de) Nichtklebrige ueberzugs- und klebstoffzusammensetzungen

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20050406

AK Designated contracting states

Kind code of ref document: A2

Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IT LI LU MC NL PT RO SE SI SK TR

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN

18D Application deemed to be withdrawn

Effective date: 20090505