US20040049972A1 - Method for producing adhesive polyacrylates using mercapto functional photoinitiators - Google Patents

Method for producing adhesive polyacrylates using mercapto functional photoinitiators Download PDF

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US20040049972A1
US20040049972A1 US10/343,523 US34352303A US2004049972A1 US 20040049972 A1 US20040049972 A1 US 20040049972A1 US 34352303 A US34352303 A US 34352303A US 2004049972 A1 US2004049972 A1 US 2004049972A1
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radicals
groups
added
psa
polymerization
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Marc Husemann
Stephan Zollner
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Tesa SE
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Tesa SE
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Publication of US20040049972A1 publication Critical patent/US20040049972A1/en
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    • 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
    • C08F2/00—Processes of polymerisation
    • C08F2/46—Polymerisation initiated by wave energy or particle radiation
    • C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
    • 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
    • C08F2/00—Processes of polymerisation
    • C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
    • 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
    • C08F2/00—Processes of polymerisation
    • C08F2/46—Polymerisation initiated by wave energy or particle radiation
    • 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
    • C08F20/00—Homopolymers and 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
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/10—Esters
    • C08F20/12—Esters of monohydric alcohols or phenols

Definitions

  • the invention relates to a process for preparing pressure-sensitively adhesive polyacrylates by free-radical addition polymerization.
  • PSAs Pressure sensitive adhesives
  • the PSAs employed for these purposes must have certain properties, such as, for example, good surface tack, high cohesion, good tack at low and high temperatures, and good thermal load-bearing capacity.
  • U.S. Pat. No. 4,144,157 describes UV-crosslinkable PSAs which have been synthesized, for example, from acrylic esters and from (meth)acrylic acid 2-alkoxy-2-phenyl-2-benzoylethyl esters. Disadvantageous again is the low reactivity of these photoinitiators and the associated low cohesion of the PSAs prepared.
  • U.S. Pat. No. 4,737,559 discloses UV-crosslinkable acrylic PSAs containing copolymerizable (meth)acryloylbenzophenone derivatives in the polymer chain. These PSAs were specifically conceived for use in the medical sector, such as for plasters, for example.
  • DE 38 44 445 A1 describes UV-crosslinkable PSAs based on (meth)acrylic ester polymers, which comprise a UV-reactive, copolymerized monomer in the form of an N-substituted (meth)acrylamide-benzophenone derivative; a (meth)acryloyloxy-benzophenone derivative or a styrene-benzophenone derivative.
  • UV-crosslinkable PSAs based on isoamyl (meth)acrylate copolymers are described in DE 38 36 968 A1. These PSAs are based on ⁇ - ⁇ -monoolefinically unsaturated acids whose homopolymers possess a glass transition temperature of below ⁇ 30° C., on monoolefinically unsaturated acids and/or their anhydride, on further olefinically unsaturated monomers containing functional groups, and on a polymerizable (meth)acryloyloxybenzophenone or acetophenone derivative. Although the room temperature cohesion of the PSAs thus prepared; following brief UV irradiation, is acceptable, the thermal load-bearing capacity is inadequate.
  • copolymerized photoinitiators fulfill only the function of UV crosslinking after coating. Accordingly it is necessary, for example, for preparing acrylic PSAs in acetone, to add regulators, so that the polymerization can be conducted with only a low solvent fraction and gelling of the polymer is avoided.
  • the reduction in the solvent fraction is of great interest particularly for polyacrylate-based hotmelt PSAs, since in this case, following polymerization, the solvent has to be removed, which is laborious, and it would therefore be desirable to minimize the amounts used, on economic and environmental grounds.
  • U.S. Pat. No. 5,942,555 used regulators likewise containing a photoinitiator to prepare telechelic polymers, and subsequently activated them with UV light.
  • Sulfur compounds in PSAs are known from the field of the rubber adhesives. There, they serve as stabilizers; see in this respect DE 198 26 103 A1, which describes the use of solid monothiols, soluble or dispersible in rubber, as stabilizers in melted PSAs based on natural rubber or synthetic rubbers, suitable tackifier resins, and promoters for the purpose of increasing the radiation crosslinking yield.
  • Polyfunctional (meth)acrylates can be added here as crosslinking promoters.
  • Claim 1 relates accordingly to a process for preparing pressure-sensitively adhesive polyacrylates by free-radical addition polymerization, in which mercapto-functionalized photoinitiators of the general formula (I) and/or (II)
  • R and R′ being chosen independently of one another from the following groups:
  • radicals which comprise one or more of the substituted or unsubstituted radicals specified under a).
  • the fraction of the compounds (I) and/or (II) is from 0.01 to 5% by weight, based on the monomers employed.
  • the polymerization takes place using a monomer mixture which comprises at least the following component:
  • R 2 an alkyl chain having 2-20 carbon atoms
  • Examples of monomers from group a) are butyl, pentyl, hexyl, heptyl, octyl, isooctyl, 2-methylheptyl, 2-ethylhexyl, nonyl, decyl, dodecyl, lauryl or stearyl (meth)acrylate or (meth)acrylic acid.
  • group b) examples include maleic anhydride, styrene, styrene compounds, vinyl acetate, (meth)acrylamides, N-substituted (meth)acrylamides, ⁇ -pacryloyloxypropionic acid, vinylacetic acid, fumaric acid, crotonic acid, aconitic acid, dimethylacrylic acid, trichloroacrylic acid, itaconic acid, vinyl acetate, hydroxyalkyl (meth)acrylate, amino-containing (meth)acrylates, hydroxyl-containing (meth)acrylates, with particular preference 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate and/or 4-hydroxybutyl (meth)acrylate, and double-bond-functionalized photoinitiators.
  • composition of the corresponding monomers is preferably chosen such that the resultant adhesives possess pressure-sensitively adhesive properties in accordance with D. Satas [Handbook of Pressure Sensitive Adhesive Technology, 1989, VAN NOSTRAND REINHOLD, New York].
  • the free radical polymerization can be carried out in the presence of one or more organic solvents and/or in the presence of water or without solvent. It is preferred to use as little solvent as possible. Depending on conversion and temperature, the polymerization time is between 6 and 48 h.
  • solvents used include preferably esters of saturated carboxylic acids (such as ethyl acetate), aliphatic hydrocarbons (such as n-hexane or n-heptane), ketones (such as acetone or methyl ethyl ketone), special boiling point spirit or mixtures of these solvents.
  • esters of saturated carboxylic acids such as ethyl acetate
  • aliphatic hydrocarbons such as n-hexane or n-heptane
  • ketones such as acetone or methyl ethyl ketone
  • special boiling point spirit or mixtures of these solvents special boiling point spirit or mixtures of these solvents.
  • stabilizers and emulsifiers which are familiar to the skilled worker for this purpose to the polymerization.
  • Polymerization initiators used include customary radical-forming compounds such as peroxides, azo compounds, and peroxosulfates, for example. Initiator mixtures can also be used.
  • polymerization regulators it is possible, for example to use alcohols and ethers.
  • the polymerization may be carried out in polymerization reactors, which are generally provided with a stirrer, two or more feed vessels, reflux condenser, heating and cooling, and are equipped for operation under N 2 atmosphere and superatmospheric pressure.
  • the polymerization medium can be rermoved under reduced pressure, this operation being carried out at elevated temperatures, for example, and advantageously in the range from 80 to 150° C.
  • the polymers can then be used in solvent-free state, particularly as hotmelt PSAs. Depending on further processing and field of application it may also be of advantage to prepare the polymers of the invention without solvent.
  • the polymers of the invention can be modified in customary fashion.
  • tackifying resins such as terpene, terpenephenolic, C5, C9, C5/C9 hydrocarbon, pinene or indene resins or rosins, alone or in combination with one another.
  • various fillers e.g., chalk, carbon black, glass microbeads, etc.
  • aging inhibitors as additives.
  • crosslinkers, and UV crosslinking promoters that are known to the skilled worker are admixed.
  • Polyfunctional acrylate crosslinkers are particularly advantageous for the preparation of star polymers.
  • the polymers are advantageously applied conventionally by brushing, spraying, rolling, knifecoating, pouring or extruding, where appropriate at elevated temperature—usually in the temperature range from 20 to 150° C.—to substrates suitable as carrier materials for this purpose: for example, to paper, paperboard, wood, metals, and polymer films, made for example from plasticized PVC; polyethylene, polyamides, polyethylene glycol terephthalate or polypropylene. Where solvents are used, they can easily be evaporated from the coatings, where appropriate at room temperature or slightly elevated temperatures, generally at temperatures of 20-150° C., preferably of 50-100° C., using, customarily, radiant heaters or heated-air circulation apparatus.
  • the pressure-sensitively adhesive polyacrylates are crosslinked by ultraviolet radiation in a wavelength range from 200 to 400 nm.
  • Crosslinking of the hotmelt PSAs of the invention takes place advantageously by brief UV irradiation with commercially customary high-pressure or medium-pressure mercury lamps having an output of, for example, from 80 to 160 W/cm. It may be appropriate to adapt the output of the lamp to the belt speed or, if the belt is running slowly, to shade off the belt partly in order to reduce the thermal load thereon.
  • the irradiation time depends on the construction and output of the respective lamps.
  • the invention relates, moreover, to the use of the pressure-sensitively adhesive polyacrylates prepared by the inventive process to produce PSA articles, particularly for producing an adhesive tape comprising an acrylic PSA applied to one or both sides of a backing.
  • the UV-curing polyacrylates prepared by the inventive process are particularly suitable as melts or as solutions for preparing PSA materials having improved tack, improved bond strength, and high cohesion, such as PSA tapes, PSA sheets or PSA labels.
  • films of polyethylene glycol terephthalate were coated with an adhesive application of 50 g/m 2 .
  • dissolved polymers are used for adhesive performance testing
  • the solvents are evaporated in a drying oven at 120° C. for 10 minutes.
  • the dry PSA films were irradiated using an Eltosch unit with medium-pressure mercury lamps.
  • the distance of the UV lamps from the irradiated PSA films was 5 cm, the output of the UV lamps is 120 W/cm.
  • the product was diluted with 150 ml of chloroform, washed with 5 times 250 ml of 0.1 N hydrochloric acid, dried over sodium sulfate and finally recrystallized twice from 15:1 toluene/hexane. 12.9 g (65% yield) of the product were isolated.
  • the different phases were separated with a centrifuge and the aqueous phase was extracted with three times 50 ml of chloroform.
  • the combined organic phases were dried over sodium sulfate.
  • the mother liquor was diluted with water and the precipitated product was filtered off, dissolved again in chloroform and then washed with 10% strength aqueous sodium hydrogen carbonate solution, 1 N hydrochloric acid and water. The product was used without further purification.
  • a strip 20 mm wide of an acrylic PSA laminated onto a polyester film was applied to steel plates washed twice with acetone and once with isopropanol.
  • the PSA strip was pressed onto the substrate twice using a 2 kg weight.
  • the adhesive tape was then immediately peeled from the substrate at a speed of 300 mm/min and at an angle of 180°. All. measurements were conducted at room temperature under standardized climatic conditions.
  • a strip of the adhesive tape 13 mm wide was applied to a smooth steel surface cleaned three times with acetone and once with isopropanol. The area of application was 20 mm ⁇ 13 mm (length ⁇ width). The adhesive tape was then pressed onto the steel substrate four times using a 2 kg weight. A 1 kg weight was fastened to the adhesive tape at room temperature and at 70° C.
  • a conventional 2 L glass reactor equipped with a mechanical stirrer, reflux condenser, internal temperature sensor and a heating bath was charged with 320 g of 2-ethylhexyl acrylate, 56 g of butyl acrylate, 20 g of acrylic acid, 200 g of acetone and 4 g of 4-mercaptomethylbenzophenone. After 30 minutes of nitrogen gas inertization, the reaction mixture was heated to an internal temperature of 58° C. with stirring and then 0.2 g of AIBN (azoisobutyronitrile) was added 0.2 g of AIBN was added after a reaction time of 1.5 h, and 100 g of acetone after 3 h.
  • AIBN azoisobutyronitrile
  • the PSA tape was dried in a drying oven at 120° C. for 10 minutes.
  • the PSA specimen was subsequently irradiated in a UV unit (from Eltosch) with a UV lamp (120 W/cm, 254 nm) in 2 passes at 20 m/min.
  • UV-crosslinked PSA tapes were tested for bond strength on steel (test method A) and for cohesion by a shear test at room temperature and at 70° C. (test method B).
  • a conventional 2 L glass reactor equipped with a mechanical stirrer, reflux condenser, internal temperature sensor and a heating bath was charged with 320 g of 2-ethylhexyl acrylate, 56 g of butyl acrylate, 20 g of acrylic acid, 200 g of acetone and 4 9 of Ebecryl ⁇ P 36 (acrylated benzophenone derivative from UCB).
  • the reaction mixture was heated to an internal temperature of 58° C. with stirring and then 0.2 g of AIBN (azoisobutyronitrile) was added.
  • AIBN azoisobutyronitrile
  • 0.2 g of AIBN was added after a reaction time of 1.5 h, 100 g of acetone after 3 h.
  • 0.2 g of Perkadox ⁇ 16 bis(4-tert-butylcyclohexanyl) peroxydicarbonate
  • a conventional 2 L glass reactor equipped with a mechanical stirrer, reflux condenser, internal temperature sensor and a heating bath was charged with 320 g of 2-ethylhexyl acrylate, 56 g of butyl acrylate, 20 g of acrylic acid, 200 g of acetone/isopropanol (97:3) and 4 g of Ebecryl ⁇ P 36 (acrylated benzophenone derivative from UCB). After 30 minutes of nitrogen gas inertization, the reaction mixture was heated to an internal temperature of 58° C with stirring and then 0.2 g of AIBN (azoisobutyronitrile) was added.
  • AIBN azoisobutyronitrile
  • 0.2 9 of AIBN was added after a reaction time of 1.5 h, and 100 g of acetone/isopropanol (97:3) after 3 h. After 8 and 10 hours of reaction, in each case 0.2 g of Perkadox ⁇ 16 (bis(4-tert-butylcyclohexanyl) peroxydicarbonate) was added, and after 10 h a further 100 g of acetone/isopropanol (97:3) were added for dilution. The polymerization was terminated after 24 h by cooling. The product was a polymer having a molecular weight of 760 000 g/mol (M w from gel permeation chromatography).
  • the PSA thus prepared was diluted down to 35% (solids) with acetone and then applied at 50 g/m 2 (solids after drying) to a primed PET (polyethylene terephthalate) film 23 ⁇ m thick.
  • the PSA tape was dried in a drying oven at 120° C. for 10 minutes.
  • the PSA specimen was subsequently irradiated in a UV unit (from Eltosch) with a UV lamp (120 W/cm, 254 nm) in 2 passes at 20 m/min.
  • UV-crosslinked PSA tapes were tested for bond strength on steel (test method A) and for cohesion by a shear test at room temperature and at 70° C. (test method B).
  • a conventional 2 L glass reactor equipped with a mechanical stirrer, reflux condenser, internal temperature sensor and a heating bath was charged with 360 g of 2-ethylhexyl acrylate, 34 g of acrylic acid, 200 g of acetone and 6 g of N-(2-mercaptoethyl)-4-benzoylbenzamide. After 30 minutes of nitrogen gas inertization, the reaction mixture was heated to an internal temperature of 58° C. with stirring, and subsequently the procedure of example 7 was followed.
  • the product is a polymer having a molecular weight of 710 000 g/mol (M w from gel permeation chromatography).
  • the PSA thus prepared was diluted down to 35% (solids) with acetone and then applied at 50 g/m 2 (solids after drying) to a primed PET (polyethylene terephthalate) film 23 ⁇ m thick.
  • the PSA tape was dried in a drying oven at 120° C. for 10 minutes.
  • the PSA specimen was subsequently irradiated in a UV unit (from Eltosch) with a UV lamp (120 W/cm, 254,nm) in 2 passes at 20 m/min.
  • UV-crosslinked PSA tapes were tested for bond strength on steel (test method A) and for cohesion by a shear test at room temperature and at 70° C. (test method B).
  • a conventional 2 L glass reactor equipped with a mechanical stirrer, reflux condenser, internal temperature sensor and a heating bath was charged with 360 g of 2-ethylhexyl acrylate, 34 g of acrylic acid, 200 g of acetone and 6 g of benzoin acrylate (prepared by the method of Guse et al. in accordance with DE 27 43 979 A1).
  • the reaction mixture was heated to an internal temperature of 58° C. with stirring and then 0.2 g of AIBN (azoisobutyronitrile) was added 0.2 g of AIBN was added after a reaction time of 1.5 h, 100 g of acetone after 3 h.
  • 0.2 g of Perkadox ⁇ 16 bis(4-tert-butylcyclohexanyl) peroxydicarbonate
  • a conventional 2 L glass reactor equipped with a mechanical stirrer, reflux condenser, internal temperature sensor and a heating bath was charged with 360 g of 2-ethylhexyl acrylate, 34 g of acrylic acid, 200 g of acetone/isopropanol (97:3) and 6 g of benzoin acrylate (prepared by the method of Guse et al. in accordance with DE 27 43 979 A1). After 30 minutes of nitrogen gas inertization, the reaction mixture was heated to an internal temperature of 58° C. with stirring, and subsequently the procedure of example 7 was followed. The product was a polymer having a molecular weight of 750,000 g/mol (M w from gel permeation chromatography).
  • the PSA thus prepared was diluted down to 35% (solids) with acetone. and then applied at 50 g/m 2 (solids after drying) to a primed PET (polyethylene terephthalate) film 23 ⁇ m thick.
  • the PSA tape was dried in a drying oven at 120° C. for 10 minutes.
  • the PSA specimen was subsequently irradiated in a UV unit (from Eltosch) with a UV lamp (120 W/cm, 254 nm) in 2 passes at 20 m/min.
  • UV-crosslinked PSA tapes were tested for bond strength on steel (test method A) and for cohesion by a shear test at room temperature and at 70° C. (test method B).
  • the mercapto-functionalized photo-initiator is very suitable for preparing acrylic PSAs by the inventive process. There is no need to supply any regulator to the polymerization (examples 7+10).
  • Comparison with examples 9 and 12 shows that acrylated photoinitiators can be copolymerized by the addition of a regulator.
  • the polymers prepared by the process of the invention were diluted down to 35% (solids) with acetone and then applied at 50 g/m 2 (solids after drying) to a primed PET (polyethylene terephthalate) film 23 ⁇ m thick.
  • the PSA tapes were dried in a drying oven at 120° C. for 10 minutes.
  • the PSA specimens were subsequently irradiated in a UV unit (from Eltosch) with a UV lamp (120 W/cm, 254 nm),in 2 passes at 20 m/min.
  • UV-crosslinked PSA tapes were tested for bond strength on steel (test method A) and for cohesion by a shear test at room temperature and at 70° C. (test method B).

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Adhesive Tapes (AREA)
  • Polymerisation Methods In General (AREA)
US10/343,523 2000-08-11 2001-08-08 Method for producing adhesive polyacrylates using mercapto functional photoinitiators Abandoned US20040049972A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10039212.1 2000-08-11
DE10039212A DE10039212A1 (de) 2000-08-11 2000-08-11 Verfahren zur Herstellung haftklebriger Polyacrylate unter Verwendung mercaptofunktionalisierter Photoinitiatoren
PCT/EP2001/009151 WO2002014378A1 (de) 2000-08-11 2001-08-08 Verfahren zur herstellung haftklebriger polyacrylate unter verwendung mercaptofunktionalisierter photoinitiatoren

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US20040049972A1 true US20040049972A1 (en) 2004-03-18

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US10/343,523 Abandoned US20040049972A1 (en) 2000-08-11 2001-08-08 Method for producing adhesive polyacrylates using mercapto functional photoinitiators

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US (1) US20040049972A1 (de)
EP (1) EP1311554B1 (de)
JP (1) JP2004506756A (de)
DE (2) DE10039212A1 (de)
ES (1) ES2230356T3 (de)
WO (1) WO2002014378A1 (de)

Cited By (7)

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US7271203B2 (en) 2001-11-24 2007-09-18 Tesa Aktiengesellschaft Crosslinking of photoiniator-initialized polyacrylates
WO2008054137A1 (en) * 2006-11-01 2008-05-08 Lg Chem, Ltd. Acrylic pressure-sensitive adhesive composition for polarizing plate, containing a photo-initiator group
US20080132601A1 (en) * 2006-12-05 2008-06-05 Hoyle Charles E Benzophenone/thioxanthone derivatives and their use in photopolymerizable compositions
US20130150479A1 (en) * 2011-07-29 2013-06-13 Insight High Technology (Beijing) Co. Ltd. Mercapto Benzophenone Compounds, Compositions and Preparation Method Thereof
US9410028B2 (en) 2009-08-12 2016-08-09 Tesa Se Process for preparing polyacrylates
US20180243463A1 (en) * 2015-08-31 2018-08-30 3M Innovative Properties Company Negative pressure wound therapy dressings comprising (meth)acrylate pressure-sensitive adhesive with enhanced adhesion to wet surfaces
CN115701428A (zh) * 2021-08-02 2023-02-10 上海发微医用材料有限公司 一种光引发剂及其应用

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DE102016200055A1 (de) 2016-01-06 2017-07-06 Volkswagen Ag Flussfeldplatte und Bipolarplatte sowie Brennstoffzelle

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US4737559A (en) * 1986-05-19 1988-04-12 Minnesota Mining And Manufacturing Co. Pressure-sensitive adhesive crosslinked by copolymerizable aromatic ketone monomers
US5026742A (en) * 1988-08-20 1991-06-25 Basf Aktiengesellschaft Radiation-crosslinkable contact adhesive mixtures
US5026806A (en) * 1988-10-31 1991-06-25 Basf Aktiengesellschaft UV-crosslinkable materials based on isoamyl (meth)acrylate copolymers
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Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7402632B2 (en) 2001-11-24 2008-07-22 Tesa Aktiengesellschaft 2-Component crosslink of end-functionalized polyacrylates
US7271203B2 (en) 2001-11-24 2007-09-18 Tesa Aktiengesellschaft Crosslinking of photoiniator-initialized polyacrylates
US8337961B2 (en) 2006-11-01 2012-12-25 Lg Chem, Ltd. Acrylic pressure-sensitive adhesive composition for polarizing plate, containing a photo-initiator group
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JP2004506756A (ja) 2004-03-04
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ES2230356T3 (es) 2005-05-01
DE10039212A1 (de) 2002-02-21
DE50104419D1 (de) 2004-12-09

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