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WO2007144255A1 - Adhésif sensible à la pression contenant une émulsion polymère comprenant du butyl(méth)acrylate tertiaire - Google Patents

Adhésif sensible à la pression contenant une émulsion polymère comprenant du butyl(méth)acrylate tertiaire Download PDF

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Publication number
WO2007144255A1
WO2007144255A1 PCT/EP2007/055112 EP2007055112W WO2007144255A1 WO 2007144255 A1 WO2007144255 A1 WO 2007144255A1 EP 2007055112 W EP2007055112 W EP 2007055112W WO 2007144255 A1 WO2007144255 A1 WO 2007144255A1
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WO
WIPO (PCT)
Prior art keywords
monomers
pressure
sensitive adhesive
polymer
meth
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Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/EP2007/055112
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German (de)
English (en)
Inventor
Cornelis Petrus Beyers
Petra SCHÖCKER
Stefan Kirsch
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BASF SE
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BASF SE
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Filing date
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Application filed by BASF SE filed Critical BASF SE
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Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • C09J133/062—Copolymers with monomers not covered by C09J133/06
    • C09J133/066—Copolymers with monomers not covered by C09J133/06 containing -OH groups

Definitions

  • the invention relates to a pressure-sensitive adhesive comprising an aqueous polymer dispersion prepared by emulsion polymerization, characterized in that the polymer contains tertiary-butyl (meth) acrylate and monomers having hydroxyl groups (in short, hydroxy monomers).
  • the invention relates to a process for the preparation of the pressure-sensitive adhesive and the use of the pressure-sensitive adhesive.
  • Adhesive adhesives require both good adhesion to the substrate and sufficient internal strength in the adhesive layer (cohesion). Adhesion and cohesion are opposite performance properties. Measures that improve adhesion generally result in cohesion deterioration and vice versa.
  • Pressure-sensitive adhesives based on aqueous polymer dispersions obtainable by emulsion polymerization have long been known.
  • these are polyacrylates.
  • An improvement in the adhesion and cohesion has been achieved in such emulsion polymers hitherto by selecting suitable comonomers or additives.
  • suitable comonomers or additives By way of example, reference is made to DE-A 103 23 048, according to which positive effects are achieved by adding silicon compounds to the polymer dispersion.
  • Object of the present invention was pressure-sensitive adhesives with improved adhesion and / or cohesion.
  • the initially defined pressure-sensitive adhesive was found. Also found was a process for its preparation.
  • the pressure-sensitive adhesive according to the invention contains as essential constituent an aqueous polymer dispersion which is prepared by emulsion polymerization;
  • the dispersed polymer is therefore an emulsion polymer.
  • the emulsion polymer is preferably at least 40 wt .-%, preferably at least 60 wt .-%, more preferably at least 80 wt .-% of so-called main monomers.
  • the main monomers are selected from C 1 to C 20 alkyl (meth) acrylates, vinyl esters of carboxylic acids containing up to 20 C atoms, vinylaromatics having up to 20 C atoms, ethylenically unsaturated nitriles, vinyl halides, vinyl ethers of alcohols having from 1 to 10 C atoms, aliphatic hydrocarbons having 2 to 8 C atoms and one or two double bonds or mixtures of these monomers.
  • (meth) acrylic acid alkyl ester having a Ci-Cio-alkyl radical such as methyl methacrylate, methyl acrylate, n-butyl acrylate, ethyl acrylate and 2-ethylhexyl acrylate.
  • mixtures of (meth) acrylic acid alkyl esters are also suitable.
  • Vinyl esters of carboxylic acids having 1 to 20 carbon atoms are, for. As vinyl laurate, stearate, vinyl propionate, vinyl versatate and vinyl acetate.
  • Suitable vinylaromatic compounds are vinyltoluene, ⁇ - and p-methylstyrene, ⁇ -butylstyrene, 4-n-butylstyrene, 4-n-decylstyrene and preferably styrene.
  • nitriles are acrylonitrile and methacrylonitrile.
  • the vinyl halides are ethylenically unsaturated compounds substituted with chlorine, fluorine or bromine, preferably vinyl chloride and vinylidene chloride.
  • vinyl ethers are, for. As vinyl methyl ether or vinyl isobutyl ether. Vinyl ether is preferably from 1 to 4 C-containing alcohols.
  • hydrocarbons having 2 to 8 carbon atoms and one or two olefinic double bonds may be mentioned ethylene, propylene, butadiene, isoprene and chloroprene.
  • Preferred main monomers are the C 1 to C 10 -alkyl acrylates and methacrylates, in particular C 1 to C 8 -alkyl acrylates and methacrylates, and vinylaromatics, in particular styrene and mixtures thereof.
  • methyl acrylate methyl methacrylate, ethyl acrylate, n-butyl acrylate, n-hexyl acrylate, octyl acrylate and 2-ethylhexyl acrylate, styrene and mixtures of these monomers. More preferably, the polymer is at least 40 wt .-%, in particular at least 60 wt .-% and most preferably at least 80 wt .-% of C1-C20-, in particular Ci-CioAlkyl (meth) acrylates.
  • the polymer contains tertiary butyl acrylate or tertiary butyl methacrylate (short tertiary butyl (meth) acrylate), preferably the polymer contains tertiary butyl acrylate.
  • the polymer contains hydroxyl groups-containing monomers (short hydroxy monomers).
  • Suitable hydroxy-monomers are, in particular, hydroxyalkyl (meth) acrylates. It may be z. B. to C2 to C20- in particular to C2 to C10 and more preferably to C2 to Ce hydroxyalkyl (meth) acrylates act.
  • hydroxybutyl acrylate or hydroxybutyl methacrylate (hydroxybutyl (meth) acrylate for short).
  • the butyl chain of the hydroxybutyl (meth) acrylate is preferably unbranched, it is an n-butyl chain.
  • the OH group is preferably at the terminal C atom, therefore it is 4-hydroxy-n-butyl (meth) acrylate.
  • Particularly preferred are the acrylates over the methacrylates, most preferably is the 4-hydroxy-n-butyl acrylate.
  • the amount of hydroxy monomers contained in the polymer is preferably at least 0.1% by weight, more preferably at least 0.3% by weight, very preferably at least 0.5% by weight and in particular at least 1% by weight. ; the amount of hydroxy monomers contained in the polymer is generally not greater than 5 wt .-%, more preferably not greater than 4.5 wt .-% and in particular not greater than 3 wt .-%. All weights are based on the polymer.
  • the polymer may contain other monomers, eg. B. monomers with acid groups (short acid monomers) z. As monomers with carboxylic acid, sulfonic acid or phosphonic acid groups. Preferred are carboxylic acid groups. Called z. As acrylic acid, methacrylic acid, itaconic acid, maleic acid or fumaric acid.
  • the polymer may contain acid monomers in amounts of 0.1 to 5, more preferably 0.2 to 4, most preferably 0.5 to 3 wt .-%, based on the polymer.
  • Phenyloxyethylglycol mono (meth) acrylate, glycidyl acrylate, glycidyl methacrylate, amino (meth) acrylates such as 2-aminoethyl (meth) acrylate may also be mentioned as further monomers.
  • Other monomers which may also be mentioned are crosslinking monomers.
  • the glass transition temperature of the polymer is preferably -60 to 0 ° C, more preferably -60 to -1O 0 C and most preferably -60 to -2O 0 C.
  • the glass transition temperature can be determined by conventional methods such as differential thermal analysis or differential scanning calorimetry (see, for example, ASTM 3418/82, so-called “mid-point temperature”).
  • the polymers are prepared by emulsion polymerization, which is therefore an emulsion polymer.
  • ethylenically unsaturated compounds are polymerized in water using ionic and / or nonionic emulsifiers and / or protective colloids or stabilizers as surface-active compounds for stabilizing the monomer droplets and the polymer particles later formed from the monomers.
  • Emulsifiers are both anionic, cationic as also nonionic emulsifiers into consideration.
  • Anionic and nonionic emulsifiers are preferably used as surface-active substances.
  • emulsifiers are z.
  • ethoxylated fatty alcohols (EO degree: 3 to 50, alkyl: Cs to C36), ethoxylated mono-, di- and tri-alkylphenols (EO degree: 3 to 50, alkyl: C 4 - to Cg), alkali metal salts of dialkyl esters of sulfosuccinic acid and of alkali metal and ammonium salts of alkyl sulfates (alkyl radical: Cs to C12), of ethoxylated alkanols (EO degree: 4 to 30, alkyl radical: C12 to Cis), of ethoxylated alkylphenols (EO degree: 3 to 50, alkyl radical: C 4 to Cg), of alkylsulfonic acids (alkyl radical: C 12 to Cis) and of alkylarylsulfonic acids (alkyl radical: Cg to Cis).
  • emulsifiers are compounds of the general formula II
  • R 5 and R 6 are hydrogen or C 4 - to Cu-alkyl and are not hydrogen at the same time, and X and Y may be alkali metal ions and / or ammonium ions.
  • R 5 , R 6 are linear or branched alkyl radicals having 6 to 18 C atoms or hydrogen and in particular having 6, 12 and 16 C atoms, wherein R 5 and R 6 are not both simultaneously hydrogen.
  • X and Y are preferably sodium, potassium or ammonium ions, with sodium being particularly preferred.
  • Particularly advantageous are compounds II in which X and Y are sodium, R 5 is a branched Al kylrest with 12 C atoms and R 6 is hydrogen or R 5 .
  • Industrial mixtures are used which have a share of 50 to 90 wt .-% of the monoalkylated product, for example Dowfax ® 2A1 (trademark of Dow Chemical Company).
  • Suitable emulsifiers can also be found in Houben-Weyl, Methods of Organic Chemistry, Volume 14/1, Macromolecular substances, Georg Thieme Verlag, Stuttgart, 1961, pages 192 to 208.
  • emulsifiers are z. B. Dowfax ® 2 A1, Emulan ® NP 50, Dextrol ® OC 50, 825 emulsifier, emulsifier 825 S, Emulan ® OG, Texapon ® NSO, Nekanil ® 904 S, Lumiten ® I-RA, Lumiten E 3065, Disponil FES 77 , Lutensol AT 18, Steinapol VSL, E-mulphor NPS 25.
  • the surfactant is usually used in amounts of from 0.1 to 10% by weight, based on the monomers to be polymerized.
  • water-soluble initiators are usually used for the radical polymerization of the monomers.
  • Water-soluble initiators for the emulsion polymerization are z.
  • ammonium and alkali metal salts of peroxodisulfuric z.
  • sodium peroxodisulfate, hydrogen peroxide or organic peroxides z.
  • red-ox reduction-oxidation
  • the redox initiator systems consist of at least one mostly inorganic reducing agent and one inorganic or organic oxidizing agent.
  • the oxidation component is z. B. to the above-mentioned initiators for emulsion polymerization.
  • the reduction components are, for.
  • alkali metal salts of sulfurous acid such as.
  • sodium sulfite, sodium hydrogen sulfite, alkali salts of Dischwef- ligen acid such as sodium disulfite
  • bisulfite addition compounds aliphatic aldehydes and ketones such as acetone bisulfite or reducing agents such as hydroxymethanesulfinic and their salts, or ascorbic acid.
  • the red-ox initiator systems can be used with the concomitant use of soluble metal compounds whose metallic component can occur in multiple valence states.
  • Usual Red Ox initiator systems are z. As ascorbic acid / iron (II) sulfate / sodium peroxydisulfate, tert-butyl hydroperoxide / sodium disulfite, tert-butyl hydroperoxide / Na hydroxymethanesulfinic.
  • the individual components eg. As the reduction component, mixtures may also be z.
  • the compounds mentioned are usually used in the form of aqueous solutions, the lower concentration being determined by the amount of water acceptable in the dispersion and the upper concentration by the solubility of the compound in question in water.
  • the concentration is 0.1 to 30 wt .-%, preferably 0.5 to 20 wt .-%, particularly preferably 1, 0 to 10 wt .-%, based on the solution.
  • the amount of initiators is generally 0.1 to 10 wt .-%, preferably 0.5 to 5 wt .-%, based on the monomers to be polymerized. It is also possible to use several different initiators in the emulsion polymerization.
  • regulators can be used. Regulators cause a chain termination reaction and thus reduce the molecular weight of the polymer.
  • the regulators are bound to the polymer, generally at the end of the chain.
  • the amount of regulator may in particular 0.05 to 4 parts by weight, particularly preferably 0.05 to 0.8 parts by weight and very particularly preferably 0.1 to 0.6 parts by weight, based on 100 wt. Parts of the monomers to be polymerized. Suitable regulators are in particular compounds having a mercapto group such as tertiary
  • the regulators are generally low molecular weight compounds having a molecular weight of less than 2000, in particular less than 1000 g / mol.
  • the emulsion polymerization is generally carried out at 30 to 130, preferably 50 to 90 ° C.
  • the polymerization medium may consist of water only, as well as of mixtures of water and thus miscible liquids such as methanol. Preferably, only water is used.
  • the feed process can be carried out in a stepwise or gradient mode. Preference is given to the feed process in which a part of the polymerization batch is initially introduced, heated to the polymerization temperature, polymerized and then the remainder of the polymerization batch, usually over several spatially separate feeds, one or more of which contain the monomers in pure or in emulsified form, continuously, stepwise or under superposition of a concentration gradient while maintaining the polymerization of the polymerization zone supplies. In the polymerization can also z. B. be presented for better adjustment of the particle size of a polymer seed.
  • the manner in which the initiator is added to the polymerization vessel in the course of the free radical aqueous emulsion polymerization is known to one of ordinary skill in the art. It can be both completely charged into the polymerization vessel, as well as according to its consumption in the course of the radical aqueous
  • Emulsion polymerization are used continuously or stepwise. In particular, this depends on the chemical nature of the initiator system as well as on the polymerization temperature. Preferably, a part is initially charged and the remainder supplied according to the consumption of the polymerization.
  • a subset of the monomers may, if desired, be initially charged in the polymerization vessel at the beginning of the polymerization, the other monomers, or all monomers, if no monomers are introduced, are added in the feed process during the polymerization.
  • the regulator can be partially submitted, be added in whole or in part during the polymerization or towards the end of the polymerization.
  • dispersions with the highest possible solids content are preferred.
  • solids contents> 60 wt .-% you should set a bimodal or polymodal particle size, otherwise the viscosity is too high, and the dispersion is no longer manageable.
  • the generation of a new particle generation can be carried out, for example, by adding seed (EP 81 083), by adding excess amounts of emulsifier or by adding miniemulsions.
  • Another benefit associated with low viscosity at high solids content is improved coating behavior at high solids levels.
  • the generation of a new / new particle generation (s) can take place at any time. It depends on the particle size distribution desired for a low viscosity.
  • the monomers are added continuously at least partially during the polymerization. In some cases, monomers can also be initially charged in the polymerization vessel before the beginning of the polymerization.
  • a maximum of 30% by weight of the total amount of the monomers is initially charged in the polymerization vessel.
  • the remaining monomers ie preferably at least 70% by weight, more preferably at least 80% by weight, most preferably at least 90% by weight are continuously added during the polymerization.
  • no monomers are initially charged, ie the total amount of the monomers is fed in during the polymerization.
  • the individual components can be added to the reactor in the feed process from above, in the side or from below through the reactor bottom.
  • the tertiary butyl (meth) acrylate is added to the polymerization mixture completely or at least partially only towards the end of the emulsion polymerization.
  • tBA tertiary butyl (meth) acrylate
  • the term "monomer" is intended to include both not yet polymerized monomers and monomer units of the polymer, ie. H. the polymerized monomers understood.
  • the above residual amount tBA is in particular at least 85% by weight, more preferably at least 95% by weight and most preferably 100% by weight of the tertiary butyl (meth) acrylate.
  • the residual amount tBA is fed to the end of the emulsion polymerization, ie after all other monomers have already been added to the polymerization mixture.
  • the monomers added to the polymerization mixture are preferably already predominantly polymerized, ie. H. the polymerization mixture is at the beginning of the addition of the residual amount of tBA to at least 80 wt .-%, more preferably at least 90 wt .-%, most preferably at least 95 wt .-% of already formed polymer.
  • the total residual amount tBA is preferably in a short period of time (generally less than 30 minutes, in particular less than 20 Minutes, more preferably less than 15 minutes) is added; it is therefore preferably a swelling polymerization.
  • aqueous dispersions of the polymer are generally obtained with solids contents of 15 to 75 wt .-%, preferably from 40 to 75 wt .-%.
  • the polymer thus prepared is preferably used in the form of its aqueous dispersion.
  • the polymer is preferably used as or in pressure-sensitive adhesives.
  • the pressure-sensitive adhesive preferably contains the polymer in the form of the aqueous polymer dispersion as obtained or obtainable by the emulsion polymerization.
  • the pressure-sensitive adhesive can consist exclusively of the polymer or of the aqueous dispersion of the polymer.
  • the pressure-sensitive adhesive may also contain other additives.
  • Tackifiers are z. From Adhesive Age, July 1987, pages 19-23 or Polym. Mater. Be. Closely. 61 (1989), pages 588-592.
  • Tackifiers are z.
  • natural resins such as rosins and their by disproportionation or isomerization, polymerization, dimerization, hydrogenation resulting derivatives.
  • These may be in their salt form (with, for example, mono- or polyvalent counterions (cations) or preferably in their esterified form.)
  • Alcohols which are used for the esterification may be mono- or polyvalent Examples are methanol, ethanediol, Diethylene glycol, triethylene glycol, 1, 2,3-propanethiol, pentaerythritol.
  • hydrocarbon resins eg., coumarone-indene resins, polyester terpene resins, hydrocarbon resins based on unsaturated C-H compounds, such as butadiene, pentene, methylbutene, isoprene, piperylene, divinylmethane, pentadiene, cyclopentadiene, cyclopentadiene, cyclohexadiene, styrene, a-methylstyrene , Vinyltoluene use.
  • tackifiers are increasingly also polyacrylates, which have a low molecular weight used. Preferably, these polyacrylates have a weight-average molecular weight M w below 30,000.
  • the polyacrylates are preferably at least 60, in particular at least 80 wt .-% of Ci-C8-alkyl (meth) acrylates.
  • Preferred tackifiers are natural or chemically modified rosin resins. Rosin resins consist predominantly of abietic acid or abietic acid derivatives.
  • the tackifiers can be added in a simple manner to the polymers according to the invention, preferably to the aqueous dispersions of the polymers.
  • the tackifiers are preferably themselves in the form of an aqueous dispersion.
  • the amount by weight of the tackifiers is preferably 5 to 100 parts by weight. more preferably 10 to 50 parts by weight. based on 100 parts by weight of polymer (solid / solid).
  • thickeners preferably associative thickeners, defoamers, plasticizers, pigments, wetting agents or fillers when used as a pressure-sensitive adhesive use.
  • the pressure-sensitive adhesives according to the invention therefore optionally contain, in addition to the aqueous polymer dispersion, tackifiers and / or the above additives.
  • the pressure-sensitive adhesives for a better wetting of surfaces, the pressure-sensitive adhesives, in particular wetting aids, z.
  • wetting aids As fatty alcohol ethoxylates, Alkylphenolethoxylate, sulfosuccinic, Nonylphenolethoxylate, polyoxyethylene / -propylenes or sodium dodecylsulfonate included. The amount is generally 0.05 to 5 parts by weight, in particular 0.1 to 3 parts by weight per 100 parts by weight of polymer (solid).
  • the pressure-sensitive adhesives are suitable for the production of self-adhesive articles such as labels, films or adhesive tapes.
  • the pressure-sensitive adhesive can be prepared by conventional methods, for. B. by rolling, knife coating, brushing, etc. on carriers, eg. As paper or polymer films, preferably consisting of polyethylene, polypropylene, which may be stretched biaxially or monoaxially, polyethylene terephthalate, polyvinyl chloride, polystyrene, polyamide or metal are applied.
  • carriers with non-polar surfaces for.
  • the water may preferably be removed by drying at 50 to 150 ° C.
  • the carriers can be cut into adhesive tape, labels or films before or after application of the adhesive.
  • the pressure-sensitive adhesive fabric coated side of the substrates, with a release paper, z. For example, be covered with a silikon- nized paper.
  • the self-adhesive articles according to the invention have very good adhesive properties, in particular a good adhesion to the substrates and a high cohesion (internal strength in the adhesive layer). They also have a good adhesion to nonpolar surfaces and are therefore particularly suitable for substrates with nonpolar surfaces, eg. B. Polyolefinober vom, z. As polyethylene (HDPE or LDPE) or polypropylene.
  • Feed 1 was an aqueous emulsion prepared from
  • Feed 2 was 45.69 g of a 7% strength by weight aqueous solution of sodium peroxodisulfate.
  • Feed 3 was pure tert-butyl acrylate in the amount:
  • Feed 4 was 9 g of a 10% by weight aqueous solution of t-butyl hydroperoxide.
  • Feed 5 was 7.24 g of a 12% by weight aqueous solution of Rongalit C.
  • the internal temperature of the reactor was lowered to 25 ° C.
  • the aqueous polymer dispersion obtained had a solids content of 53.5% by weight.
  • the mean particle size was 200 nm.
  • the polymer dispersions were coated on a polyethylene film as carrier (in the transfer process, coating first of silicone paper and transfer to polyethylene) at an application rate of 19 g / m 2 and dried at 90 ° C. for 3 minutes. Subsequently, the peel strength (adhesion) and shear strength (cohesion) were determined.
  • the pressure-sensitive adhesive coated carrier was cut into 25 mm wide test strips. To determine the shear strength, the test strips were adhered to steel with a bonded area of 6.25 cm 2, rolled once with a 1 kg roll, stored for 10 min (in standard atmosphere, 50% relative humidity 1 bar, 23 ° C) and then suspended with a 1 kg weight (in standard climate). The measure of shear strength was the time in hours until the weight dropped; in each case the average of 5 measurements was calculated.
  • a 2.5 cm wide test strip was glued to a steel test specimen and rolled once with a 1 kg roller. He was then clamped with one end in the upper jaws of a tensile-strain tester. The tape was peeled off the test surface at 300 mm / min. At a 180 ° angle, i. H. the adhesive strip was bent over and pulled off parallel to the test sheet, and the required effort was measured. The measure of peel strength was the force in N / 2.5 cm, which resulted as an average of five measurements.
  • the peel strength was determined 24 hours after the bonding. After this time, the adhesive power has fully developed.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Polymerisation Methods In General (AREA)

Abstract

L'invention concerne un adhésif sensible à la pression, contenant une dispersion polymère aqueuse obtenue par polymérisation en émulsion, caractérisé en ce qu'il contient le polymère de butyl(méth)acrylate et des monomères contenant des groupements hydroxy (en abrégé des monomères hydroxy).
PCT/EP2007/055112 2006-06-12 2007-05-25 Adhésif sensible à la pression contenant une émulsion polymère comprenant du butyl(méth)acrylate tertiaire Ceased WO2007144255A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP06115295 2006-06-12
EP06115295.5 2006-06-12

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WO2007144255A1 true WO2007144255A1 (fr) 2007-12-21

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8152944B2 (en) 2008-05-09 2012-04-10 Tesa Se Pressure-sensitive adhesive tapes for bonding printing plates

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0515719A1 (fr) * 1991-05-31 1992-12-02 Sellotape AG Copolymères d'acrylates auto-adhésifs, procédé de leur préparation et objets plats auto-adhésifs les contenants

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0515719A1 (fr) * 1991-05-31 1992-12-02 Sellotape AG Copolymères d'acrylates auto-adhésifs, procédé de leur préparation et objets plats auto-adhésifs les contenants

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8152944B2 (en) 2008-05-09 2012-04-10 Tesa Se Pressure-sensitive adhesive tapes for bonding printing plates

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