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.

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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)
• Adhesives Or Adhesive Processes (AREA)
• Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
• Adhesive Tapes (AREA)
• Sealing Material Composition (AREA)

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• 2002
  • 2002-11-14 DE DE10252978A patent/DE10252978A1/de not_active Withdrawn
• 2003
  • 2003-10-31 AU AU2003301964A patent/AU2003301964A1/en not_active Abandoned
  • 2003-10-31 US US10/534,347 patent/US20060052561A1/en not_active Abandoned
  • 2003-10-31 CN CNB2003801031581A patent/CN100334121C/zh not_active Expired - Fee Related
  • 2003-10-31 WO PCT/EP2003/012116 patent/WO2004044021A2/de active Application Filing
  • 2003-10-31 EP EP03810955A patent/EP1560859A2/de not_active Withdrawn
  • 2003-10-31 KR KR1020057008499A patent/KR20050089003A/ko not_active Application Discontinuation
  • 2003-10-31 JP JP2004550904A patent/JP2006506476A/ja active Pending
  • 2003-11-04 TW TW092130778A patent/TWI289579B/zh not_active IP Right Cessation

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