WO2013083670A1 - Adhésifs polyuréthanes sensibles à la pression réactifs - Google Patents

Adhésifs polyuréthanes sensibles à la pression réactifs Download PDF

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Publication number
WO2013083670A1
WO2013083670A1 PCT/EP2012/074592 EP2012074592W WO2013083670A1 WO 2013083670 A1 WO2013083670 A1 WO 2013083670A1 EP 2012074592 W EP2012074592 W EP 2012074592W WO 2013083670 A1 WO2013083670 A1 WO 2013083670A1
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WIPO (PCT)
Prior art keywords
radicals
sensitive adhesives
polyurethane prepolymers
adhesive
alkoxysilane
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PCT/EP2012/074592
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German (de)
English (en)
Inventor
Mathias Matner
Evelyn Peiffer
Axel Schmidt
Michael Ludewig
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Bayer Intellectual Property Gmbh
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Publication of WO2013083670A1 publication Critical patent/WO2013083670A1/fr

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Classifications

    • 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
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
    • C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
    • C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
    • C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
    • C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
    • 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
    • C08G18/28—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
    • C08G18/4866—Polyethers having a low unsaturation value
    • 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
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
    • C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
    • C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
    • C08G18/7671—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups containing only one alkylene bisphenyl group
    • 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
    • C09J175/08—Polyurethanes from polyethers
    • 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
    • C08G2170/00—Compositions for adhesives
    • C08G2170/40—Compositions for pressure-sensitive adhesives

Definitions

  • the present invention relates to the use of special alkoxysilane and OH-terminated polyurethane prepolymers as reactive pressure-sensitive adhesives or as a component of reactive pressure-sensitive adhesives.
  • Pressure-sensitive adhesives have been known for a long time. Due to their positive environmental impact, bonding with these adhesives has become an integral part of modern manufacturing processes. Suitable pressure-sensitive adhesives have a permanent tack, good wetting behavior for various surfaces and a balanced level of adhesion and cohesion.
  • Standard pressure-sensitive adhesives are not chemically reactive. They do not change during the bonding process and in the application. They have a permanent surface tack that allows bonding by means of contact pressure, but without the supply of energy.
  • the long-term adhesive properties of a pressure-sensitive adhesive bond are essentially determined by the viscoelastic and plastic deformation behavior under load, which is a decisive disadvantage of standard pressure-sensitive adhesives: under static tensile shear stress, these adhesives tend to creep, resulting in reduced tensile strength, in extreme cases For this reason, reactive adhesives are increasingly being developed which crosslink after application by chemical reactions to form covalent bonds, thereby increasing the maximum operating temperature, improving solvent resistance and significantly improving creep under static tensile shear stress ,
  • Acrylate-based reactive pressure-sensitive adhesives are described by way of example in US Pat. No. 4,737,559.
  • the pressure-sensitive adhesives described there are crosslinkable by UV radiation and represent a substantial improvement over the standard pressure-sensitive adhesives.
  • the problem with these UV-crosslinkable pressure-sensitive adhesives is that the complex UV technology fails with complicated geometries of the workpieces to be bonded ,
  • alkoxysilane-functional polymers More suitable as reactive pressure-sensitive adhesives are alkoxysilane-functional polymers.
  • Alkoxy silane-functional polyacrylate polymers are described by way of example in US Pat. No. 4,112,213 or WO 2004/011568.
  • the alkoxysilane-functional polyacrylate polymers described there have, in principle, no defined 'silane functionality' but a statistical see distribution of alkoxysilane groups within the polymer chains. Therefore, the reproducible adjustment of the adhesive properties in reactive pressure-sensitive adhesives based on alkoxysilane-functional polyacrylate polymers is problematic.
  • alkoxysilane-functional polyester polymers such as are described by way of example in WO 2008/027496 are more suitable. In the case of bonding with binders based on polyesters, however, there is basically the problem of ester hydrolysis due to hydrolysis, which is why such adhesives frequently fail under permanent exposure to moisture.
  • Alkoxysilane-functional polyurethane polymers based on polyether polyols are therefore of particular interest as binders for reactive pressure-sensitive adhesives.
  • Corresponding products are described by way of example in EP-A 1 715 015, EP-A 0 336 431, WO 2006/134995 and WO 2009/106699.
  • tackifying resins may be required, which is explicitly described in all publications mentioned. These resins are needed to enhance tack, but are not attached to the binder. They can therefore migrate from the adhesive film to the interface of the substrate and remain so after detachment of the adhesive tape on the substrate. This non-residue-free removal interferes with many applications, in particular when polymethylmethacrylate (PMMA) was used as a substrate.
  • PMMA polymethylmethacrylate
  • the removal of adhesive residues is very common. to scratch the surface or if the adhesive residues have been removed by means of organic solvents to a matte finish.
  • alkoxysilane and OH-functional polyurethane prepolymers as pressure-sensitive adhesive or as a constituent of pressure-sensitive adhesives is within the scope of the teaching of DE-A
  • alkoxysilane and OH-functional polyurethane prepolymers with polyester, polyether, poly (meth) acrylate or polybutadiene structure are generally described as binders for pressure-sensitive adhesives.
  • polyether-based prepolymers according to the invention show no inherent adhesion.
  • the invention relates to the use of alkoxysilane and OH-terminated polyurethane prepolymers obtained by reacting
  • Isocyanate-functional polyurethane prepolymers prepared by incomplete, stopped at a conversion of 50 to 90 wt .-% of the OH groups of the polyol component of i) an aromatic, aliphatic or cycloaliphatic diisocyanate component having an NCO content of 20 to 60 wt .-% with ii) a polyol component comprising as a main component a polyoxyalkylene diol having a molecular weight of 3000 to 30,000, with
  • X, Y, Z are identical or different, optionally branched, C 1 -C 8 -alkyl or C 1 -C -alkoxy radicals, with the proviso that at least one of the radicals is a C 1 -C 5 -alkoxy group,
  • R is optionally branched alkylene radicals having 1 to 8 carbon atoms
  • R ' is hydrogen, optionally branched C 1 -C 8 -alkyl radicals,
  • R "and R” ' denote identical or different, optionally branched alkyl radicals having 1 to 8 carbon atoms as a constituent of reactive pressure-sensitive adhesives.
  • the invention is based on the surprising observation that the alkoxysilane- and O-H-functional polyether-polyurethane prepolymers to be used according to the invention themselves have a sufficient intrinsic tack, adhere perfectly to PMMA and can be removed without residue.
  • alkoxysilane- and OH-functional polyether-polyurethane prepolymers to be used according to the invention as pressure-sensitive adhesives or as constituents of pressure-sensitive adhesives are known in principle and are described in EP-A 1 474 460. According to the teaching of this publication, these prepolymers are, in special formulations, highly elastic in construction - Sealants used. The possible use as an adhesive is mentioned, but not a use for the production of reactive pressure-sensitive adhesives.
  • the isocyanate prepolymers A) to be used according to the invention are prepared by reacting a diisocyanate component i) with a polyol component ii) which is characterized in more detail below.
  • polyisocyanate component i) isocyanates which can be used according to the invention are any aliphatic, cycloaliphatic or aromatic diisocyanates of the prior art with an isocyanate content of from 20 to 60% by weight.
  • component i) or part of component i) are preferably suitable aromatic or cycloaliphatic diisocyanates of molecular weight range 174 to 300 g / mol such as 4,4'-diphenylmethane diisocyanate, optionally in admixture with 2,4'-diphenylmethane diisocyanate, 2,4-diisocyanatotoluene its technical mixtures with preferably up to 35 wt .-%, based on the mixture, of 2,6-diiso- cyanatotoluene, l-isocyanato-3,3,5-trimethyl-5-isocyanatomethylcyclohexane (IPDI), bis (4 - Isocyanatocyclo
  • component i) 1-isocyanato-3,3,5-trimethyl-5-isocyanato-methylcyclohexane (IPDI), 4,4'-diphenylmethane diisocyanate, 2,4'-diphenylmethane diisocyanate and the mixtures of these isomeric diisocyanates or 2, 4-diisocyanatotoluene, 2,6-diisocyanatotoluene and the mixtures of these isomeric diisocyanates used.
  • IPDI 1-isocyanato-3,3,5-trimethyl-5-isocyanato-methylcyclohexane
  • 4'-diphenylmethane diisocyanate 4,4'-diphenylmethane diisocyanate, 2,4'-diphenylmethane diisocyanate and the mixtures of these isomeric diisocyanates or 2 4-diisocyanatotoluene, 2,6-diisocyanato
  • the preparation of the polyurethane prepolymers A) is carried out in accordance with the teaching of EP-A 1 474 460.
  • the diisocyanate component i) is reacted with a polyol component ii) such that 10 to 50 wt .-% of the OH groups of the polyol component ii) not reacted with the NCO groups of the diisocyanate component i), so that in the produced polyurethane prepolymer A) 50 to 90 wt .-% of the OH groups of the polyol component ii) are implemented.
  • the polyol component ii) consists essentially of at least one polyoxyalkylenediol which has a molecular weight of 3000 to 30 000 g / mol (corresponding to an OH number of 37.3 to 3.7), preferably 4000 to 25000 g / mol (corresponding to a OH number from 28 to 5.1).
  • the polyoxyalkylene diols which can preferably be used according to the invention can be prepared by ethoxylation in a manner known per se from polyurethane chemistry. tion and / or propoxylation of suitable starter molecules are produced.
  • Suitable starter molecules are any diols such as, for example, ethylene glycol, propylene glycol, 1,3-butanediol, 1,4-butanediol, 1,6-hexanediol, 2-ethylhexanediol-1,3, or else primary monoamines, for example aliphatic amines, such as ethylamine or butylamine.
  • polyoxyalkylenediols have a mean, calculated from OH content and functionality molecular weight of 3000 to 30000 g / mol, preferably 4000 to 25000 g / mol and an ethylene oxide content of at most 40 wt .-%, based on the total weight of the polyoxyalkylene.
  • component ii polypropylene oxide polyethers having a terminal unsaturation of not more than 0.04 meq / g and a mean molecular weight of 8,000 to 22,000 g / mol calculated from OH content and functionality.
  • polyether polyols having a low degree of unsaturation which are particularly preferably usable according to the invention are known in principle and are described by way of example in EP-A 2 83 148 and US Pat. No. 3,278,457.
  • NCO prepolymers A) can continue to be used minor amounts of polyfunctional polyether polyols of the prior art.
  • the preparation of the inventively used as component A) polyurethane prepolymers by reaction of the diisocyanate component (i) with the diol component (ii) in the temperature range of 40 to 120 ° C, preferably 50 to 100 ° C while maintaining an NCO / OH Equivalent ratio of 1.1: 1 to 2.0: 1, preferably 1.1: 1 to 1.6: 1.
  • the reaction is stopped as soon as a reaction of 50-95% by weight of the OH groups of the polyol component, preferably 70-95% by weight of the OH groups of the polyol component, has been achieved, ie the polyol component is still 5 to 50 Wt .-%, preferably 5 to 30 wt .-% of free, not reacted with NCO groups OH groups.
  • the conversion is determined by an NCO titrimetric method customary in polyurethane chemistry.
  • the reaction is stopped by the addition of a small amount of a mineral or organic acid such as hydrochloric acid, sulfuric acid, phosphoric acid or its derivatives, formic acid, acetic acid or another alkane or organic acid or an acid-releasing component such as acid halides or acidic acid. hydrides.
  • a mineral or organic acid such as hydrochloric acid, sulfuric acid, phosphoric acid or its derivatives
  • formic acid acetic acid or another alkane or organic acid or an acid-releasing component
  • acid halides such as acid halides or acidic acid. hydrides.
  • formic acid chloride acetic acid chloride
  • propionic acid chloride and benzoyl chloride.
  • benzoyl chloride as stopper is preferred. If appropriate, it is also possible to dispense with the use of the stopper and to add the amino silane compound directly.
  • the inventively employable polyurethane prepolymers A) have an NCO content of 0, 1 to 2.0 wt .-%, preferably 0, 1 to 1, 0 wt .-%. Depending on the ratio of NCO to OH groups, this corresponds to an average molecular weight of 4200 to 84000 g / mol, preferably 8400 to 84000 g / mol, calculated from the NCO content and functionality.
  • inventively employable polyurethane prepolymers A) are reacted in the second stage of the process according to the invention with compounds of the formula (I)
  • X, Y, Z are identical or different, optionally branched C 1 -C 6 -alkyl or C 1 -C 8 -alkoxy radicals, with the proviso that at least one of the radicals is a C 1 -C 8 -alkoxy group,
  • R is optionally branched alkylene radicals having 1 to 8 carbon atoms, preferably 1 to 4 carbon atoms,
  • R ' is hydrogen, optionally branched C 1 -C 8 -alkyl radicals, C 6 -C 10 -aryl radicals or radicals of the general formula (II)
  • R "and R '" are identical or different, optionally branched alkyl radicals having 1 to 8 carbon atoms, preferably 1 to 4 carbon atoms.
  • the reaction of the NCO prepolymers with the alkoxysilane- and amino-containing compounds of the formula (I) in the process according to the invention takes place within a temperature range from 0 to 150.degree. C., preferably from 20 to 80.degree. C., the quantity ratios generally being selected in this way be used that per mole of NCO groups used 0.95 to 1.1 mol aminosilane compound. Preferably, 1 mole of aminosilane compound is used per mole of NCO groups used.
  • higher reaction temperatures are used, according to the teaching of EP-A 0 807 649, a cyclocondensation reaction may occur, which is by no means disturbing and may even be advantageous at times.
  • the polyurethane prepolymers containing alkoxysilane and OH groups which are used as pressure-sensitive adhesives or as constituents of pressure-sensitive adhesives are viscous products which are liquid at room temperature.
  • crosslinking catalysts are added to the prepolymers to be used according to the invention.
  • the usual additives for pressure sensitive adhesives may be added to the adhesives, such as fillers, solvents, desiccants, adhesion promoters, plasticizers, polymer stabilizers and, although not required according to the invention, tackifying resins.
  • all catalysts which accelerate the silane polycondensation are suitable as crosslinking catalysts.
  • titanates eg, tetrabutyl titanate, tetrapropyl titanate, etc.
  • Tin carbonate salts eg, dibutyltin dilaurate, dibutyltin maleate, dibutyltin diacetate, tin octylates, tin naphthenates, etc.
  • organic zirconium compounds eg, zirconium tetraisopropoxide, zirconium tetrabutoxides, etc.
  • Reaction products of dibutyltin oxide with phthalates Chelating agents such as organic aluminum compounds (eg, aluminum trisacetylacetonates, aluminum trisethyl acetoacetonates, diisopropoxyaluminum ethylacetoacetonates, etc.), dibutyltin diacetyl acetonates, zirconium tetraacetyl acetonates, titanium t
  • Aminic curing catalysts are particularly preferably used. Of course, mixtures of the catalysts mentioned can be used.
  • the crosslinking catalysts are used in amounts of from 0.01 to 1% by weight, preferably from 0.05 to 0.5% by weight, based on the amount of the prepolymer.
  • polymer stabilizers it is possible to use all polymer stabilizers known for stabilizing polyetherurethanes.
  • anti-oxidants such as sterically hindered phenols, phosphites, phosphonites, UV absorbers of the benzophenone or triazole type and also UV protectants based on sterically hindered amines.
  • Particularly advantageous are mixtures of said stabilizers. Stabilization with the aid of antioxidants and UV protectors based on sterically hindered amines is particularly preferred.
  • Silica acids, calcium carbonate, talc, titanium oxide, zinc oxide, silica and barium sulfate may be mentioned as examples of suitable fillers.
  • surface-treated fillers or mixtures of fillers may also be used. According to the invention, only small amounts of fillers corresponding to a mass fraction ⁇ 10% are used to prepare the pressure-sensitive adhesives. It is essential that the fillers to be used have a low moisture content, so that the storage stability of the adhesive formulation is not adversely affected.
  • organic solvents may be advantageous. It is possible to use the solvents customary in adhesive technology, whereby attention must also be paid here to a low water content.
  • suitable solvents are: ethyl acetate, butyl acetate, methyl ethyl ketone, methyl isobutyl ketone, methoxypropyl acetate, ethylene glycol monoethyl ether acetate, toluene, xylene, white spirit or any desired mixtures of these solvents.
  • alkoxysilyl compounds may be added.
  • suitable drying agents are nyltrimethoxysilane, methyltrimethoxysilane, i-butyltrimethoxysilane, hexadecyltrimethoxysilane.
  • Such desiccants only have to be used if formulation components which can contain moisture are used.
  • the pressure-sensitive adhesives adhesion promoter can be added to achieve good adhesion to problematic substrates.
  • Suitable adhesion promoters are the known functional silanes such as aminosilanes of the abovementioned type from he and N-aminoethyl-3-aminopropyl-trimethoxy and / or N-aminoethyl-3-amino-propyl-methyl-dimethoxysilane, epoxy silanes and / or mercaptosilanes.
  • the co-use of the adhesion promoter can hinder the residue-free removal of adhesive residues and is therefore less preferred.
  • the pressure-sensitive adhesives according to the invention may contain plasticizers.
  • suitable plasticizers are the known phthalic acid esters, phosphoric esters, sulfonic esters and propylene glycols. Pressure-sensitive adhesives containing no plasticizers are preferred.
  • the pressure-sensitive adhesives according to the invention can furthermore also comprise tackifying resins, although their use is by no means preferred, since the presence of such resins prevents residue-free removal and is counterproductive for the purposes of the invention.
  • tackifying resins are phenolic resins, modified phenolic resins (eg, cashew oil-modified phenolic resins, tall oil-modified phenolic resins, etc.), terpene-phenolic resins, xylene-phenolic resins, cyclopentadiene-phenolic resins, xylene resins, petroleum resins, phenol-modified petroleum resins. low molecular weight polystyrene resins or terpene resins.
  • the pressure-sensitive adhesives according to the invention preferably contain only crosslinking catalysts and polymer stabilizers in addition to the alkoxysilane and OH-containing polyurethane prepolymers.
  • the adhesives show excellent adhesion to metallic substrates as well as to various plastics with markedly low creep under static tensile shear stress.
  • Pressure-sensitive adhesives, which contain only crosslinking catalysts and polymer stabilizers, can be easily removed from the substrate without any residue, eliminating the need for time-consuming removal of adhesive residues. Especially good is the adhesion to PMMA. With this characteristic profile, the pressure-sensitive adhesives according to the invention are outstandingly suitable for
  • coated substrates such as adhesive tapes, adhesive films and adhesive labels, of which at least part of the surface is coated with a layer of the invention is coated according to pressure-sensitive adhesive.
  • coated substrates or articles preferably adhesive tapes, adhesive films and adhesive labels also subject of the present invention.
  • the following examples are intended to illustrate the essence of the invention without limiting it.
  • RT room temperature
  • the viscosity measurements were carried out in accordance with ISO / DIN 3219: 1990 at a constant temperature of 23 ° C. and a constant shear rate of 250 / sec with a plate cone rotation type Physica MCR viscometer (Anton Paar Germany GmbH, Ostfildern, DE). using the measuring cone CP 25-1 (25mm diameter, 1 ° cone angle).
  • the resulting polymers are mixed with the amounts of catalyst mentioned in Table 1 and homogenized.
  • a 100 ⁇ m (wet) thick film of the polymer was applied to a film with the aid of a doctor blade. Subsequently, the polymer-coated film was stored for 7 days at 23 ° C and 50% relative humidity, cut into 1.5 cm wide and 12 cm long strips and added with 2 kg contact pressure (roller) on the substrate. After 1 and 7 days, the 90 ° peel test (speed: 300 mm / min at a 90 ° angle, measuring section (Lm): 7 cm) was carried out.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

La présente invention concerne l'utilisation de prépolymères de polyuréthane spéciaux, comportant des groupes terminaux alcoxysilane et OH, comme adhésifs sensibles à la pression réactifs ou comme composants d'adhésifs sensibles à la pression réactifs.
PCT/EP2012/074592 2011-12-09 2012-12-06 Adhésifs polyuréthanes sensibles à la pression réactifs WO2013083670A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE201110088170 DE102011088170A1 (de) 2011-12-09 2011-12-09 Reaktive Haftklebstoffe
DE102011088170.0 2011-12-09

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WO2013083670A1 true WO2013083670A1 (fr) 2013-06-13

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Cited By (3)

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Publication number Priority date Publication date Assignee Title
US9708509B2 (en) 2012-10-09 2017-07-18 Avery Dennison Corporation Adhesives and related methods
US10526511B2 (en) 2016-12-22 2020-01-07 Avery Dennison Corporation Convertible pressure sensitive adhesives comprising urethane (meth)acrylate oligomers
US11049421B2 (en) 2015-02-05 2021-06-29 Avery Dennison Corporation Label assemblies for adverse environments

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