WO2011043269A1 - Procédé de fabrication de composition d'agent adhésif et de film adhésif, composition de matière première pour agent adhésif, et film adhésif - Google Patents

Procédé de fabrication de composition d'agent adhésif et de film adhésif, composition de matière première pour agent adhésif, et film adhésif Download PDF

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Publication number
WO2011043269A1
WO2011043269A1 PCT/JP2010/067275 JP2010067275W WO2011043269A1 WO 2011043269 A1 WO2011043269 A1 WO 2011043269A1 JP 2010067275 W JP2010067275 W JP 2010067275W WO 2011043269 A1 WO2011043269 A1 WO 2011043269A1
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Prior art keywords
pressure
sensitive adhesive
polymer
weight
monomer
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PCT/JP2010/067275
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English (en)
Japanese (ja)
Inventor
志朗 藤田
知子 池田
岳生 松山
美帆子 吉田
亜希奈 平井
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藤森工業株式会社
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Priority to CN201080044849.9A priority Critical patent/CN102549098B/zh
Priority to KR1020127009266A priority patent/KR101378451B1/ko
Publication of WO2011043269A1 publication Critical patent/WO2011043269A1/fr

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    • 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
    • C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/18—Manufacture of films or sheets
    • 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
    • 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
    • C09J133/08—Homopolymers or copolymers of acrylic acid esters
    • 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
    • C09J7/20—Adhesives in the form of films or foils characterised by their carriers
    • C09J7/22—Plastics; Metallised plastics
    • 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
    • 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
    • C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
    • C09J2203/318—Applications of adhesives in processes or use of adhesives in the form of films or foils for the production of liquid crystal displays
    • 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
    • C09J2301/40—Additional features of adhesives in the form of films or foils characterized by the presence of essential components

Definitions

  • a shock absorbing protective plate is attached to the front surface of the liquid crystal panel via an air layer to prevent the liquid crystal panel from cracking.
  • a thin protective plate is directly bonded using an adhesive layer without providing an air layer on the front surface of a mobile phone liquid crystal panel.
  • PDP in order to reduce the weight and thickness, and improve the visibility, it has been studied as a direct color filter system that an optical filter film is directly bonded to a PDP panel.
  • Patent Document 2 discloses a resin composition containing an acrylic acid derivative, an acrylic acid derivative polymer, and a high molecular weight cross-linking agent for impact absorption necessary for protecting an image display device or the like. . It is said to be useful for preventing cracks in the image display panel or relieving stress and impact and is excellent in transparency.
  • the resin sheet was placed in a high-temperature and high-humidity test tank of 60 ° C. and 90% RH for 50 hours, and as a result of confirmation by visual observation, this resin composition was transparent with little foaming. It is said to be excellent.
  • Example 18 in which slight turbidity was observed immediately after production was also evaluated as A (no white turbidity was observed in the moisture absorption test). Therefore, turbidity immediately after production is not considered. This is an inconspicuous phenomenon when a thin resin film such as polyethylene terephthalate (PET) is bonded to one or both sides, but when a gas barrier material such as an acrylic plate and glass or glass is bonded. , White turbidity starts in a few minutes immediately after taking out from the oven in an environment of 60 ° C. and 90% RH, and the white turbidity remains for several hours or more.
  • PET polyethylene terephthalate
  • Patent Document 3 a copolymer of a (meth) acrylic acid alkyl ester monomer and a carboxyl group-containing monomer is used. Also, in the case of Patent Document 3, as in Patent Document 2, it is clearly stated that the pressure-sensitive adhesive composition does not cause white turbidity of the pressure-sensitive adhesive layer even under environmental conditions of 85 ° C. and 95% RH, and a pressure-sensitive adhesive tape using the same. However, since the (meth) acrylic acid alkyl ester monomer is introduced excessively, it is necessary to irradiate the ultraviolet rays as weak as possible at the time of ultraviolet curing as in the examples for a long time.
  • the pressure-sensitive adhesive layer may be clouded even under extremely severe high-temperature and high-humidity environmental conditions such as 85 ° C. and 95% RH, which are applied to an on-vehicle display. It was not a technique that does not float and peel off the adherend and is provided with low productivity and low cost.
  • the object of the present invention is to perform an endurance test under an environmental condition at a high temperature and high humidity such as (60 ° C., 90% RH) or (85 ° C., 95% RH) using an oven. It is to provide a pressure-sensitive adhesive composition that does not cause cloudiness of the pressure-sensitive adhesive layer or lift and peel off from the adherend even after being taken out of the oven, a method for producing the same, and a pressure-sensitive adhesive film using the same.
  • a hydroxyl group-containing polymer obtained by a polymerization reaction of at least one monomer of a hydroxyl group-containing (meth) acrylate is introduced into the pressure-sensitive adhesive layer to participate in preventing aggregation of water molecules. Therefore, in the present invention, in order to solve the above problems, an acrylic polymer as a main agent is polymerized in advance, and this is a syrup in which at least one kind of hydroxyl group-containing (meth) acrylate monomer is dissolved.
  • An adhesive coating solution (a pressure-sensitive adhesive raw material composition to be a precursor of the pressure-sensitive adhesive layer) is prepared.
  • the present invention has the following configuration.
  • (I) A polymer production process for obtaining a main polymer using a mixed solvent liquid containing at least one kind of acrylic monomer; (2) Bifunctional in an amount of 0.1 equivalent or less with respect to the crosslinking point of the polymer, at least one monomer of a hydroxyl group-containing (meth) acrylate, a photopolymerization initiator, and a polymer crosslinking point.
  • a step of preparing a pressure-sensitive adhesive raw material composition containing a crosslinking agent (3)
  • a method for producing an adhesive film is provided.
  • (III) At least one kind of acrylic monomer having an ester group is polymerized from a monomer containing 85 to 95 parts by weight and at least one kind of acrylic monomer having a carboxyl group is polymerized from 5 to 15 parts by weight.
  • Main polymer 100 parts by weight;
  • the bifunctional crosslinking agent is 0.1 to 3 equivalents or less with respect to the crosslinking point of the polymer.
  • Containing And the molecular weight distribution of the said main ingredient polymer is a raw material composition for adhesives whose number average molecular weight (Mn) is 70,000 or more and whose weight average molecular weight (Mw) is 1 million or more.
  • a pressure-sensitive adhesive composition which is present in a necessary quantity in a dispersed state as much as possible. This makes it possible to adsorb moisture under high-temperature and high-humidity environmental conditions to the hydroxyl group-containing polymer, and to prevent the occurrence of white turbidity due to the aggregation of absorbed water molecules even if the pressure-sensitive adhesive layer is thickened to increase buffering properties.
  • An agent composition can be provided.
  • the water molecules are aggregated after being removed from the environmental conditions at high temperature and high humidity. It is possible to provide a method for producing a pressure-sensitive adhesive composition in which the resulting pressure-sensitive adhesive layer does not become cloudy or does not float or peel off from the adherend. According to the invention described in (II) above, even if the thickness of the pressure-sensitive adhesive layer is increased in order to increase the buffering property, water molecules are aggregated after being removed from the environmental conditions at high temperature and high humidity. It is possible to provide a method for producing a pressure-sensitive adhesive film in which the resulting pressure-sensitive adhesive layer does not become cloudy or does not float or peel off from the adherend.
  • FIG. 3A is a graph obtained by enlarging the time in the range of 0 to 40 minutes.
  • the pressure sensitive adhesive raw material composition of the present invention crosslinks at least one hydroxyl group-containing monomer (monomer B) with a polymerization initiator for polymerizing the monomer B, the main polymer (polymer A), and the main polymer. It was mixed with a crosslinking agent.
  • This raw material composition for pressure-sensitive adhesives contains at least one hydroxyl group-containing (meth) acrylate as a photopolymerizable compound that is polymerized by energy rays.
  • the polymer A is not particularly limited as long as it is the main component of the pressure-sensitive adhesive and the acrylic monomer (monomer B) containing a hydroxyl group is easily dispersed.
  • the acrylic monomer (monomer B) containing a hydroxyl group is easily dispersed.
  • an acrylic polymer is preferable, and a hydrophilic monomer is preferably copolymerized. This is because the monomer B is acrylic and contains a hydroxyl group.
  • the polymer A Is preferably an acrylic polymer.
  • the raw material composition for pressure-sensitive adhesives of the present invention When the raw material composition for pressure-sensitive adhesives of the present invention is applied to a substrate (or a separator) and dried and then polymerized by light irradiation, a pressure-sensitive adhesive film is obtained.
  • the raw material composition for pressure-sensitive adhesives of the present invention contains a cross-linking agent for cross-linking the polymer, and the content of the cross-linking agent is less than 1 equivalent to the cross-linking point of the polymer (preferably, for example, 0.5 Equivalent or less).
  • the crosslinking agent can be crosslinked with the hydroxyl group of the polymer B like an isocyanate compound, at least a part of the hydroxyl group of the polymer B is not crosslinked, and the uncrosslinked hydroxyl group is dispersed. Therefore, a pressure-sensitive adhesive layer excellent in moisture adsorption ability can be obtained.
  • the amount and type of the crosslinking agent is a bifunctional crosslinking agent in an amount of 0.1 equivalent or less with respect to the crosslinking point of the polymer, so that the deformation of the adherend can be followed.
  • the pressure-sensitive adhesive is crosslinked to impart heat resistance, and can be prevented from floating and peeling off from the adherend.
  • the pressure-sensitive adhesive film does not particularly need to be distinguished by width, and includes both pressure-sensitive adhesive tapes and pressure-sensitive adhesive sheets specified in JIS Z 0109. Specific examples thereof include a single-sided adhesive tape (or single-sided adhesive sheet) having an adhesive layer on one side of the substrate, a double-sided adhesive tape (or double-sided adhesive sheet) having an adhesive layer on both sides of the substrate, and a substrate. Transfer tape (transfer tape) in which the pressure-sensitive adhesive layer is formed in a film form without having a film.
  • the pressure-sensitive adhesive sheet can have a large area, and may be used with its wide width, or may be cut into a tape shape and used as a pressure-sensitive adhesive tape.
  • a pressure-sensitive adhesive sheet or pressure-sensitive adhesive tape wound in a roll shape is suitable for an application in which a member is bonded to a display.
  • FIG. 1A an example of the single-sided adhesive tape 5 which has the adhesive layer 2 formed using the adhesive composition of this invention is shown typically.
  • an adhesive layer 2 is formed on one side of a base material 1 that serves as a support for the adhesive layer 2, and the adhesive surface of the adhesive layer 2 is protected by a separator 3.
  • the separator 3 is peeled to expose the adhesive surface, and the base material 1 is laminated on the back surface of the pressure-sensitive adhesive layer 2 and is bonded to the adherend.
  • the structure of the double-sided pressure-sensitive adhesive tape having a base material is not particularly shown, but a pressure-sensitive adhesive layer is formed on both surfaces of the base material, and the pressure-sensitive adhesive surface of each pressure-sensitive adhesive layer has a structure protected by a separator.
  • FIG. 1B schematically shows an example of the transfer tape 6 having the pressure-sensitive adhesive layer 2 formed using the pressure-sensitive adhesive composition of the present invention.
  • separators 3 and 3 are provided on both sides of the pressure-sensitive adhesive layer 2.
  • one separator 3 is peeled off, and one adhesive surface is exposed and bonded to the adherend.
  • only the film-like pressure-sensitive adhesive layer 2 can be transferred (transferred) to the adherend by peeling off the other separator 3.
  • another adherend can be bonded to the new adhesive surface.
  • At least one kind of acrylic monomer having an ester group (—COO—) and at least one kind of acrylic monomer having a carboxyl group (—COOH) are contained as monomers that are raw materials for the polymer A.
  • various other compounds can be used.
  • an acrylic monomer having an ester group (—COO—) for example, a general formula CH 2 ⁇ CR 1 —COOR 2 (wherein R 1 is hydrogen or a methyl group, R 2 is an alkyl group having 1 to 14 carbon atoms) And (meth) acrylates such as hydroxyl group-containing (meth) acrylates.
  • alkyl (meth) acrylate represented by the general formula CH 2 ⁇ CR 1 —COOR 2 (wherein R 1 represents hydrogen or a methyl group, and R 2 represents an alkyl group having 1 to 14 carbon atoms)
  • R 1 represents hydrogen or a methyl group
  • R 2 represents an alkyl group having 1 to 14 carbon atoms
  • the alkyl group R 2 has 1 to 14 carbon atoms from the viewpoint of adhesive strength. It is not preferable that the alkyl group has 15 or more carbon atoms because the adhesive strength may be reduced.
  • the alkyl group R 2 preferably has 1 to 12 carbon atoms, preferably 4 to 12 carbon atoms, and more preferably 4 to 8 carbon atoms.
  • alkyl (meth) acrylates having 1 to 14 carbon atoms in the alkyl group R 2 alkyl (meth) acrylates having 1 to 3 or 13 to 14 carbon atoms in the alkyl group R 2 are used as a part of the monomer.
  • an alkyl (meth) acrylate having 4 to 12 carbon atoms of the alkyl group R 2 as an essential component (for example, 50 to 100 mol%).
  • these alkyl groups R 2 may be a straight chain or may be branched.
  • Examples of the hydroxyl group-containing (meth) acrylate include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, and polyethylene glycol mono (meth) acrylate. , Polypropylene glycol mono (meth) acrylate, cyclohexanedimethanol mono (meth) acrylate, and the like.
  • the acrylic monomer containing a carboxyl group include acrylic acid, methacrylic acid, maleic acid, itaconic acid, 2-acryloylethyl succinic acid, and the like.
  • acrylic monomers containing alkoxysilyl groups include ⁇ -trimethoxysilylpropyl (meth) acrylate, ⁇ -methyldimethoxysilylpropyl (meth) acrylate, and ⁇ -triethoxysilylpropyl (meth) acrylate.
  • non-acrylic monomer containing an alkoxysilyl group include vinylmethoxysilane and vinyltrimethoxysilane.
  • organic solvent used in the solution polymerization reaction examples include aromatic hydrocarbons such as toluene and xylene, aliphatic esters such as ethyl acetate and butyl acetate, and alicyclic hydrocarbons such as cyclohexane. , Aliphatic hydrocarbons such as hexane, pentane and the like, but not particularly limited as long as the polymerization reaction is not inhibited. These solvents may be used alone or in combination of two or more. What is necessary is just to determine the usage-amount of a solvent suitably.
  • the molecular weight of the polymer produced decreases as the polymerization temperature increases. In carrying out the polymerization reaction at the reflux temperature of the solvent, a polymer can be obtained while removing the heat of polymerization reaction by using a solvent having a boiling point temperature suitable for the polymerization reaction.
  • the content of monomer B (the total amount when monomer B is two or more) is preferably 5 to 20 parts by weight with respect to 100 parts by weight of the main polymer (polymer A), and is 85 ° C. 95 In the case where high durability is required such as in a test under a% RH environment, the amount is more preferably 5 to 15 parts by weight.
  • the pressure-sensitive adhesive composition comprising a known hydroxyl group-containing acrylic polymer may contain some (meth) acrylate monomers containing hydroxyl groups as unreacted monomers. Compared to the content of hydroxyl group-containing (meth) acrylate in the raw material composition for pressure-sensitive adhesives of the invention, the content is only extremely low.
  • the raw material composition for pressure-sensitive adhesives of the present invention is an acrylic syrup containing a main polymer, a hydroxyl group-containing (meth) acrylate monomer, a photopolymerization initiator, and a crosslinking agent, or coated and hydroxyl group-containing.
  • the acrylic syrup is prepared as a resin solution dissolved in an organic solvent.
  • the organic solvent used in the polymerization reaction is removed, and the obtained liquid syrup is obtained.
  • the main polymer is preferably separated and washed with water or an organic solvent as necessary. Thereby, the polymerization reaction of the main polymer can be completely stopped, and unreacted acrylic monomers can be removed from the main polymer.
  • the weight of the main polymer can be quantified more accurately, and an acrylic syrup in which the contents of the hydroxyl group-containing monomer, the crosslinking agent, and the photopolymerization initiator used in the next step are more appropriately adjusted can be produced.
  • the removal of the organic solvent used in the polymerization reaction may be performed after the hydroxyl group-containing monomer is dissolved in the main polymer.
  • the polymerization reaction may proceed when ultraviolet light contained in room light or sunlight acts on the acrylic syrup, making it difficult to manage. Is preferably added immediately before the coating step, which is a subsequent step. This is the same for resin solutions in which acrylic syrup is dissolved in an organic solvent. Care should be taken to prevent the photoinitiator from starting the reaction before coating and film formation due to some external factor. It is.
  • the raw material composition for pressure-sensitive adhesives of the present invention is preferably a pressure-sensitive adhesive coating solution containing an appropriate amount of an organic solvent in order to impart fluidity suitable for application to a substrate.
  • an organic solvent used in the adhesive coating solution include aromatic hydrocarbons such as toluene and xylene, aliphatic esters such as ethyl acetate and butyl acetate, and alicyclic carbonization such as cyclohexane. Examples thereof include aliphatic hydrocarbons such as hydrogen, hexane, and pentane, but are not particularly limited as long as the purpose of coating and dispersion can be achieved.
  • Benzophenone photopolymerization initiators include benzophenone, benzoylbenzoic acid, methyl benzoylbenzoate, methyl-o-benzoylbenzoate, 4-phenylbenzophenone, hydroxylbenzophenone, hydroxylpropylbenzophenone, acrylic benzophenone, 4,4'-bis (dimethyl) Amino) benzophenone and the like.
  • Examples of the thioxanthone photopolymerization initiator include thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, diethylthioxanthone, and dimethylthioxanthone.
  • the bifunctional crosslinking agent is not particularly limited as long as it is a compound having two functional groups that undergo crosslinking reaction in one molecule.
  • Examples of such a bifunctional crosslinking agent include a bifunctional epoxy compound and a bifunctional isocyanate.
  • the bifunctional epoxy compound include ethylene glycol diglycidyl ether, diethylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, dipropylene glycol diglycidyl ether, polypropylene glycol diglycidyl ether, and neopentyl glycol diglycidyl ether.
  • polyester such as polyethylene terephthalate (PET) and polyethylene naphthalate (PEN), polysulfone, polyethersulfone, polystyrene, polyacrylate, polyetheretherketone, polycarbonate, polyolefin such as polyethylene and polypropylene, polyamide, nylon, polyimide , Fluorine such as triacetyl cellulose (cellulose triacetate), cellulose diacetate, poly (meth) acrylic acid alkyl ester, poly (meth) acrylic acid ester copolymer, polymethyl methacrylate, polytetrafluoroethylene and polytrifluoroethylene Resin, polyvinyl chloride, polyvinylidene chloride copolymer, vinyl chloride-vinyl acetate copolymer, polyvinyl alcohol, cellophane, cellulose film, etc.
  • PET polyethylene terephthalate
  • PEN polyethylene naphthalate
  • Polysulfone polyethersulfone
  • polystyrene
  • the coating apparatus for applying the adhesive raw material composition to the substrate may be any apparatus as long as it has a means for uniformly supplying and applying the adhesive raw material composition on the base material.
  • a device comprising a tank for storing an adhesive raw material composition, a liquid feed pump, piping, a foreign matter removal filter, and a coater head so that the adhesive raw material composition can be supplied and coated on the substrate. Preferred (not shown).
  • the coater head is preferably a die coater, for example.
  • a thin film layer (coating film) of the pressure-sensitive adhesive raw material composition is formed on one side of the substrate by the coating apparatus.
  • the pressure-sensitive adhesive raw material composition immediately after coating with a coating apparatus is uncured and liquid, and has fluidity suitable for coating.
  • the thickness of the coating film is preferably between 0.05 and 3 mm, more preferably 0.1 to 2 mm.
  • the thickness of the coating film is approximately equal to the thickness of the pressure-sensitive adhesive layer obtained by photopolymerization. Therefore, the thickness of the pressure-sensitive adhesive layer in the pressure-sensitive adhesive film of the present invention is preferably between 0.05 and 3 mm, more preferably 0.1 to 2 mm.
  • the thickness of the coating film before drying is thicker than that of the syrup type, and is a number obtained by dividing the thickness of the coating film by the concentration.
  • the thickness of the coating film after drying is the same as that of the syrup type. If the coating film is too thin, the thickness of the pressure-sensitive adhesive layer is also reduced, so that the impact absorbing performance is deteriorated. Moreover, when the coating film is too thick, it is disadvantageous in that the cost increases.
  • FIG. 2 schematically shows an example of the method for producing the pressure-sensitive adhesive film of the present invention.
  • the pressure-sensitive adhesive raw material composition is supplied from the die coater 21 onto the substrate 11 to form the coating film 12.
  • Reference numeral 22 denotes a backup roll 22 that is disposed to face the die coater 21 and supports the substrate 11.
  • the base material 11 on which the coating film 12 is formed is transported along the longitudinal direction thereof, and dried in the drying chamber 23 so as to remove the solvent in the coating film 12.
  • the separator 13 is supplied from the separator supply means 24 onto the coating film 12 and bonded by a nip roll 25.
  • the temperature in the drying chamber 23 may be a temperature at which the solvent in the coating film 12 is sufficiently volatilized, and is desirably maintained at a temperature at which the polymerizable compound is not thermally polymerized.
  • the separator supply means 24 includes a roll body around which the separator 13 is wound, a shaft that holds the roll body, and the like.
  • the nip roll 25 is composed of a pair of rolls that sandwich the base material 11 on which the coating film 12 is formed and the separator 13, and is an apparatus that bonds the two together. It is preferable to provide a pressurizing means for pasting, and at least one of the rolls is preferably made of rubber so that a uniform pressure can be easily applied to the film.
  • the separator examples include polycarbonate film, polyarylate film, polyethersulfone film, polysulfone film, polyester film, polyamide film, polyimide film, polystyrene film, polyolefin film, norbornene film, phenoxy ether type polymer film, and organic permeation resistance
  • the thickness of the separator is not limited, but it is usually 5 to 500 ⁇ m, preferably 10 to 100 ⁇ m in many cases.
  • the separator is selected according to the pressure-sensitive adhesive used and the intended use (peel strength).
  • the ultraviolet irradiation device 26 includes a light source unit that generates ultraviolet light and a cooling device that removes heat generated by the light source.
  • the light source part is free of lamp light sources such as high-pressure mercury lamps and metal halide lamps, and light-emitting diodes having a light emission peak in the ultraviolet region, as long as they can obtain an ultraviolet irradiation amount that sufficiently cures the polymerizable compound in the coating film 12. Can be selected.
  • the coating film 12 polymerizes the polymerizable compound in the coating film 12 by appropriate light irradiation, thereby increasing the cohesive force and expressing adhesiveness.
  • a separator is supplied not only as the separator 13 but as the base material 11 for conveyance, and an adhesive. A layer is formed on the separator. Further, when producing a double-sided pressure-sensitive adhesive film having pressure-sensitive adhesive layers on both sides of the support as the pressure-sensitive adhesive film of the present invention, coating and drying of the coating liquid and photopolymerization of the coating film are performed simultaneously or sequentially on each side. Can be done.
  • curing for crosslinking reaction is performed.
  • the curing method is not particularly limited, for example, an adhesive film wound up on a roll is left under a predetermined temperature and time condition.
  • the curing temperature depends on the type of the crosslinking agent and the like, but is preferably heated (for example, 40 to 80 ° C.) as necessary.
  • the obtained pressure-sensitive adhesive layer has an adhesive force to glass and acrylic resin when the pressure-sensitive adhesive surface is bonded to an adherend and left in an environment of 23 ° C. and 50% RH for 1 hour and then peeled at a peeling speed of 300 mm / min. Is preferably 10 N / 25 mm or more.
  • the storage elastic modulus (G ′) at 23 ° C. and 1 Hz of the adhesive constituting the adhesive layer is 1 ⁇ 10 4 Pa or more and less than 1 ⁇ 10 6 Pa.
  • the pressure is more preferably 5 ⁇ 10 4 Pa or more and 5 ⁇ 10 5 Pa or less.
  • the storage elastic modulus When the storage elastic modulus is low, the pressure-sensitive adhesive layer is soft and easily deformed, so that it is easy to bond.
  • the two members for example, a hard material such as a glass plate or an acrylic plate
  • the pressure-sensitive adhesive film of the present invention can be suitably used as a pressure-sensitive adhesive tape for bonding members to various displays such as PDP (plasma display), liquid crystal panel, and organic EL panel.
  • PDP plasma display
  • LCD liquid crystal panel
  • organic EL panel organic EL panel
  • Transfer tapes of Examples 1 to 15 and Comparative Examples 1 to 5 were produced by the following production method using the pressure-sensitive adhesive raw material composition shown in Table 1 below. Moreover, the number average molecular weight (Mn) and the weight average molecular weight (Mw) of each main polymer were measured by the method shown in the following (Molecular weight measuring method).
  • the epoxy equivalent of the bifunctional epoxy crosslinking agent having the product name EX-931 is 172.
  • the equivalent of the crosslinking agent was calculated by using a carboxyl group as a crosslinking point in an epoxy compound and a carboxyl group and a hydroxyl group as a crosslinking point in an isocyanate.
  • the addition amount of the crosslinking agent is 0.05 equivalent with respect to the crosslinking point (AA carboxyl group) of the polymer.
  • a separator manufactured by Mitsubishi Plastics Co., Ltd .; product name; MRF, thickness 38 ⁇ m
  • MRF thickness 38 ⁇ m
  • a transfer tape having a pressure-sensitive adhesive layer formed thereon is prepared by performing UV irradiation while adjusting the amount of UV irradiation, causing a photopolymerization reaction using a photopolymerization initiator, curing at 40 ° C. for 7 days or more, and finally forming an adhesive layer. Produced.
  • a mixed solvent solution in which 87 parts by weight of 2EHA and 13 parts by weight of AA were dissolved in ethyl acetate used as an organic solvent was prepared.
  • a solution polymerization reaction was performed while refluxing the organic solvent at the boiling point to prepare a main polymer.
  • the number average molecular weight of this main polymer was 110,000, and the weight average molecular weight was 253,000.
  • 15.0 parts by weight of 4HBA, 1.0 part by weight of EX-830, and 0.10 parts by weight of Irgacure (registered trademark) 651 were dissolved in ethyl acetate used as a solvent.
  • the prepared main polymer was added to prepare a pressure-sensitive adhesive raw material composition.
  • the addition amount of a crosslinking agent is 0.02 equivalent with respect to the crosslinking point of a polymer (carboxyl group of AA). Other than that was carried out similarly to Example 1, and produced the transfer tape.
  • a transfer tape was prepared in the same manner as in Example 2 except that the pressure-sensitive adhesive raw material composition was prepared with 2.0 parts by weight of EX-830.
  • the addition amount of a crosslinking agent is 0.04 equivalent with respect to the crosslinking point of a polymer (AA carboxyl group).
  • a transfer tape was prepared in the same manner as in Example 2 except that the pressure-sensitive adhesive raw material composition was prepared with 10.0 parts by weight of 4HBA and 2.0 parts by weight of EX-830.
  • the addition amount of a crosslinking agent is 0.04 equivalent with respect to the crosslinking point of a polymer (AA carboxyl group).
  • a mixed solvent solution in which 87 parts by weight of 2EHA and 13 parts by weight of AA were dissolved in ethyl acetate used as an organic solvent was prepared.
  • a solution polymerization reaction was performed while refluxing the organic solvent at the boiling point to prepare a main polymer.
  • the main polymer had a number average molecular weight of 120,000 and a weight average molecular weight of 4,350,000.
  • a transfer tape was produced in the same manner as in Example 5 except that 10.0 parts by weight of 4HBA and 2.0 parts by weight of EX-830 were used.
  • the addition amount of a crosslinking agent is 0.04 equivalent with respect to the crosslinking point of a polymer (AA carboxyl group).
  • a transfer tape was produced in the same manner as in Example 5 except that 15.0 parts by weight of 4HBA and 2.5 parts by weight of EX-830 were used.
  • the addition amount of the crosslinking agent is 0.05 equivalent with respect to the crosslinking point (AA carboxyl group) of the polymer.
  • a mixed solvent solution in which 87 parts by weight of 2EHA and 13 parts by weight of AA were dissolved in ethyl acetate used as an organic solvent was prepared.
  • a solution polymerization reaction was performed while refluxing the organic solvent at the boiling point to prepare a main polymer.
  • the main polymer had a number average molecular weight of 140,000 and a weight average molecular weight of 1,430,000.
  • a transfer tape was prepared in the same manner as in Example 8 except that 15.0 parts by weight of 4HBA and 2.5 parts by weight of EX-830 were used.
  • the addition amount of the crosslinking agent is 0.05 equivalent with respect to the crosslinking point (AA carboxyl group) of the polymer.
  • a transfer tape was produced in the same manner as in Example 7, except that the crosslinking agent was 2.0 parts by weight of polypropylene glycol diglycidyl ether (Nagase ChemteX Corporation; product name EX-931). The addition amount of a crosslinking agent is 0.02 equivalent with respect to the crosslinking point of a polymer (carboxyl group of AA).
  • a mixed solvent solution prepared by dissolving 86.5 parts by weight of 2EHA, 13 parts by weight of AA, 0.5 parts by weight of 2-hydroxyethyl acrylate (HEA), and ethyl acetate used as an organic solvent was prepared.
  • a solution polymerization reaction was performed while refluxing the organic solvent at the boiling point to prepare a main polymer.
  • a transfer tape was produced in the same manner as in Example 12 except that 2.5 parts by weight of A-45N and 0.10 parts by weight of Irgacure (registered trademark) 651 were used.
  • the addition amount of the crosslinking agent is 0.08 equivalent with respect to the crosslinking point of the polymer (carboxyl group of AA and hydroxyl group of HEA and 4HBA).
  • the molar ratio between the crosslinking point of polymer A (carboxyl group of AA and hydroxyl group of HEA) and the crosslinking point of polymer B (hydroxyl group of 4HBA) is 1: 0.56.
  • the former has a higher ratio than the latter.
  • a mixed solvent solution in which 92 parts by weight of 2EHA and 8 parts by weight of AA were dissolved in ethyl acetate used as an organic solvent was prepared.
  • a solution polymerization reaction was performed while refluxing the organic solvent at the boiling point to prepare a main polymer.
  • the main polymer had a number average molecular weight of 90,000 and a weight average molecular weight of 1,260,000.
  • a mixed solvent solution in which 95 parts by weight of 2EHA and 5 parts by weight of AA were dissolved in ethyl acetate used as an organic solvent was prepared.
  • a solution polymerization reaction was performed while refluxing the organic solvent at the boiling point to prepare a main polymer.
  • the main polymer had a number average molecular weight of 300,000 and a weight average molecular weight of 1,440,000.
  • Example 1 A mixed solvent solution in which 87 parts by weight of 2EHA and 13 parts by weight of AA were dissolved in ethyl acetate used as an organic solvent was prepared. Using this mixed solvent liquid, a solution polymerization reaction was performed while refluxing the organic solvent at the boiling point to prepare a main polymer. The main polymer had a number average molecular weight of 120,000 and a weight average molecular weight of 4,350,000. Next, the prepared main polymer is added to a solvent solution obtained by dissolving 10.0 parts by weight of 4HBA and 0.05 parts by weight of Irgacure (registered trademark) 651 in a solvent, and then sticking. An agent raw material composition was prepared. In this case, no crosslinking agent is added. Other than that was carried out similarly to Example 1, and produced the transfer tape.
  • Irgacure registered trademark
  • Example 2 A mixed solvent solution in which 87 parts by weight of 2EHA and 13 parts by weight of AA were dissolved in ethyl acetate used as an organic solvent was prepared. Using this mixed solvent liquid, a solution polymerization reaction was performed while refluxing the organic solvent at the boiling point to prepare a main polymer. The main polymer had a number average molecular weight of 120,000 and a weight average molecular weight of 4,350,000. Next, the prepared main polymer is added to a solvent solution in which 10.0 parts by weight of 4HBA and 2.0 parts by weight of EX-830 are dissolved in the solvent used as a solvent. The ingredients were prepared. The addition amount of a crosslinking agent is 0.04 equivalent with respect to the crosslinking point of a polymer (AA carboxyl group). Other than that was carried out similarly to Example 1, and produced the transfer tape.
  • ⁇ Testing method for adhesive tape> Using the adhesive tapes (transfer tapes) of Examples 1 to 15 and Comparative Examples 1 to 5 described above, a sample is prepared, and a bubble confirmation test, a cloudiness confirmation test, a durability test, and an adhesive strength after the pasting are performed. Measurement and storage modulus measurement were performed. (Bubble confirmation test after bonding) Using a bonding device (Climb Products Co., Ltd .; product name SE320), a 50 mm ⁇ 50 mm adhesive tape is bonded to a 2 mm thick glass plate of 75 mm ⁇ 100 mm size, and then an acrylic plate is attached to the opposite surface of the adhesive tape. Pasted.
  • Example 6 which concerns on the adhesive tape of this invention is taken out from the oven immediately after taking out from the oven of a high temperature high humidity test. It can be seen that even after 60 minutes, the haze value has not changed at all, and has excellent white turbidity prevention performance. On the other hand, in Comparative Example 2, the haze value increased to about 11% as the maximum value within a few minutes immediately after taking out from the oven of the high temperature and high humidity test, and then the haze value gradually decreased with the passage of the standing time.
  • Comparative Example 1 since there is no crosslinking agent, crosslinking is insufficient and it is considered that heat resistance cannot be imparted. In Comparative Example 2, it is considered that the monomer B is not polymerized. In Comparative Example 3, the photopolymerization initiator is considered to be a problem. In Comparative Example 4, since the amount of the crosslinking agent is excessive, it becomes too hard as an adhesive tape, and it is considered that the comparative example 4 is not able to follow the deformation of the adherend and peels off. In Comparative Example 5, since the amount of acrylic acid is too large and the adhesive tape is too hard, it is considered that the acrylic tape was peeled off without being able to follow the deformation of the acrylic plate. In addition, in the case of atmospheric pressure bonding, bubbles will enter (see the bubble confirmation test after bonding above), but it disappears temporarily in the autoclave, but it re-aggregates due to the introduction of environmental test. It is also considered that foaming occurs.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Materials Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Adhesive Tapes (AREA)
  • Laminated Bodies (AREA)

Abstract

L'invention concerne une composition d'agent adhésif ainsi qu'un film adhésif ne présentant ni turbidité blanche de la couche d'agent adhésif ni instabilité et décollement par rapport au corps à coller, même après réalisation d'essais de résistance à la fatigue dans des conditions de température et d'humidité élevées mettant en œuvre un four, ni même après sortie du four. Plus précisément, l'invention concerne le procédé de fabrication d'une composition d'agent adhésif qui contient un polymère acrylique comprenant un groupe hydroxyle en tant que groupe fonctionnel, dans lequel procédé : (1) après obtention du polymère agent principal à partir d'un solvant mixte de monomère acrylique, (2) il y a préparation d'une composition de matière première pour agent adhésif qui comprend le polymère agent principal, au moins une sorte de monomère de (méth)acrylate comprenant un groupe hydroxyle, un initiateur de photopolymérisation, et une quantité d'agent de réticulation bifonctionnel allant jusqu'à 0,1 équivalent par rapport au point de réticulation du polymère, et (3) une composition d'agent adhésif est obtenue au moyen de ladite composition de matière première pour agent adhésif et par exposition à la lumière.
PCT/JP2010/067275 2009-10-06 2010-10-01 Procédé de fabrication de composition d'agent adhésif et de film adhésif, composition de matière première pour agent adhésif, et film adhésif WO2011043269A1 (fr)

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CN201080044849.9A CN102549098B (zh) 2009-10-06 2010-10-01 粘合剂组合物的制造方法、粘合薄膜的制造方法、粘合剂用原料组合物以及粘合薄膜
KR1020127009266A KR101378451B1 (ko) 2009-10-06 2010-10-01 점착제 조성물의 제조 방법, 점착 필름의 제조 방법, 점착제용 원료 조성물 및 점착 필름

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WO2013061938A1 (fr) * 2011-10-24 2013-05-02 王子ホールディングス株式会社 Feuille adhésive sensible à la pression, son procédé d'utilisation et stratifié
JP2013127012A (ja) * 2011-12-16 2013-06-27 Toyo Ink Sc Holdings Co Ltd 粘着剤、粘着シートおよびディスプレイ
JP2014024900A (ja) * 2012-07-25 2014-02-06 Nippon Zeon Co Ltd 感圧接着剤組成物、感圧接着性シート状成形体、これらの製造方法、及び表示装置
JP5859942B2 (ja) * 2012-09-26 2016-02-16 藤森工業株式会社 積層体の製造方法
JP6038660B2 (ja) * 2013-01-10 2016-12-07 日立マクセル株式会社 硬化性粘着剤組成物、粘着剤および粘着シート
US20150367600A1 (en) * 2013-02-12 2015-12-24 Mitsubishi Plastics, Inc. Transparent double-sided adhesive sheet, laminate obtained using same for constituting image display device, process for producing said laminate, and image display device obtained using said laminate
JP2015110723A (ja) * 2013-11-05 2015-06-18 日東電工株式会社 携帯電子機器部材固定用両面粘着シートおよび携帯電子機器の製造方法
JP5858347B2 (ja) * 2014-02-05 2016-02-10 大日本印刷株式会社 粘着剤組成物およびそれを用いた粘着フィルム
WO2017010501A1 (fr) * 2015-07-13 2017-01-19 王子ホールディングス株式会社 Feuille adhésive, stratifié, et leur procédé de production
JP6586072B2 (ja) * 2016-01-19 2019-10-02 富士フイルム株式会社 フィルム積層体
CN106478862A (zh) * 2016-10-24 2017-03-08 中科院合肥技术创新工程院 聚合物的快速光化学合成方法及用于该方法的反应装置
JP7063689B2 (ja) * 2017-10-06 2022-05-09 日東電工株式会社 アクリル系粘着剤組成物および粘着シート

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JPWO2017145545A1 (ja) * 2016-02-25 2018-12-06 株式会社寺岡製作所 粘着剤組成物及び粘着テープ

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