WO2017098870A1 - Composition adhésive, son procédé de production, feuille adhésive, plaque polarisante pourvue d'une couche adhésive, et stratifié - Google Patents

Composition adhésive, son procédé de production, feuille adhésive, plaque polarisante pourvue d'une couche adhésive, et stratifié Download PDF

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Publication number
WO2017098870A1
WO2017098870A1 PCT/JP2016/083901 JP2016083901W WO2017098870A1 WO 2017098870 A1 WO2017098870 A1 WO 2017098870A1 JP 2016083901 W JP2016083901 W JP 2016083901W WO 2017098870 A1 WO2017098870 A1 WO 2017098870A1
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meth
sensitive adhesive
pressure
acrylic
adhesive composition
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PCT/JP2016/083901
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English (en)
Japanese (ja)
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翔 黒澤
政一 清水
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綜研化学株式会社
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Publication of WO2017098870A1 publication Critical patent/WO2017098870A1/fr

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    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements
    • 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
    • C09J143/00—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 containing boron, silicon, phosphorus, selenium, tellurium, or a metal; Adhesives based on derivatives of such polymers
    • C09J143/04—Homopolymers or copolymers of monomers containing silicon
    • 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

Definitions

  • the present invention relates to an adhesive composition and a method for producing the same, an adhesive sheet, a polarizing plate with an adhesive layer, and a laminate.
  • the liquid crystal element has a structure in which a liquid crystal material is sandwiched between two substrates (eg, a glass plate), and a polarizing plate is attached to the surface of the substrate via an adhesive layer. Therefore, the pressure-sensitive adhesive layer constituting the liquid crystal element is required to have durability under high temperature and high humidity conditions so that it can withstand a severe use environment.
  • a technique of adding a silane coupling agent to the pressure-sensitive adhesive composition is known. Further, by increasing the surface strength of the pressure-sensitive adhesive layer, it becomes possible to prevent the pressure-sensitive adhesive layer from being heated and peeled after being placed under a high temperature and high humidity condition.
  • a technique is known in which an acrylic oligomer (acrylic tackifier) having a high glass transition temperature (Tg) is unevenly distributed on the surface of the pressure-sensitive adhesive layer (for example, Patent Document 1).
  • the acrylic tackifier is The effect of the agent was hindered, and in particular, when a glass plate was used as an adherend, there was a problem that sufficient wet heat durability could not be imparted to the pressure-sensitive adhesive layer.
  • Patent Document 2 discloses an optical pressure-sensitive adhesive composition containing an acrylic polymer and an adhesion modifier composed of a specific polymer having a hydrolyzable silyl group.
  • the polymers disclosed in the examples of Patent Document 2 have a weight average molecular weight of 55,000 to 97,000, which is problematic in compatibility with acrylic polymers.
  • An object of the present invention is to provide a pressure-sensitive adhesive composition capable of forming a pressure-sensitive adhesive layer excellent in durability under high temperature and high humidity conditions, a method for producing the same, a pressure-sensitive adhesive sheet having the pressure-sensitive adhesive layer, and a pressure-sensitive adhesive It is providing the polarizing plate with a layer, and a laminated body.
  • the present inventors diligently studied to solve the above problems. As a result, the inventors found that the above problems can be solved by a pressure-sensitive adhesive composition containing a specific (meth) acrylic polymer and a specific (meth) acrylic oligomer, and completed the present invention.
  • the present invention includes, for example, the following [1] to [9].
  • [1] A (meth) acrylic polymer (A) having a glass transition temperature (Tg) of less than 0 ° C., a hydrolyzable silyl group, and a weight average molecular weight (Mw) of 500 to 30,000, And the adhesive composition containing (meth) acrylic-type oligomer (B) whose Tg is 0 degreeC or more.
  • the monomer component is polymerized in the presence of a hydrolyzable silyl group-containing chain transfer agent, the weight average molecular weight (Mw) is 500 to 30,000, and the glass transition temperature (Tg) is 0 ° C. or higher.
  • a pressure-sensitive adhesive composition comprising a step of producing a (meth) acrylic oligomer (B), the (meth) acrylic polymer (A) having a Tg of less than 0 ° C., and the (meth) acrylic oligomer (B) Manufacturing method.
  • a monomer component containing a hydrolyzable silyl group-containing monomer is polymerized, and a (meth) acryl having a weight average molecular weight (Mw) of 500 to 30,000 and a glass transition temperature (Tg) of 0 ° C. or higher.
  • the manufacturing method of the adhesive composition containing the process which manufactures a type
  • a pressure-sensitive adhesive sheet for polarizing plate having a pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition according to any one of [1] to [4].
  • a polarizing plate with a pressure-sensitive adhesive layer comprising a polarizing plate and a pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition according to any one of [1] to [4] on at least one surface of the polarizing plate.
  • the adhesive composition which can form the adhesive layer excellent in durability under high temperature and high-humidity conditions, its manufacturing method, the adhesive sheet which has the said adhesive layer, and an adhesive A polarizing plate with a layer and a laminate can be provided.
  • polymer is used to include homopolymers and copolymers
  • polymerization is used to include homopolymerization and copolymerization.
  • acrylic and methacryl are collectively referred to as “(meth) acryl”
  • acrylate and methacrylate are collectively referred to as “(meth) acrylate”.
  • the pressure-sensitive adhesive composition of the present invention contains a (meth) acrylic polymer (A) and a (meth) acrylic oligomer (B) described below.
  • the pressure-sensitive adhesive composition preferably further contains a crosslinking agent (C), and may contain an additive (D) as necessary.
  • the (meth) acrylic polymer (A) has a glass transition temperature (Tg) of less than 0 ° C.
  • Tg of the (meth) acrylic polymer (A) can be measured with a differential scanning calorimeter, for example, by the method described in the examples.
  • the Tg of the (meth) acrylic polymer (A) is less than 0 ° C., preferably ⁇ 80 to ⁇ 10 ° C., more preferably ⁇ 60 to ⁇ 30 ° C. It is preferable from the viewpoint of the adhesiveness of the adhesive layer to the adherend that Tg is within the above range. Moreover, it is excellent from the viewpoint of being excellent in the cohesive force of an adhesive layer as Tg is more than the said lower limit, and durability improvement.
  • the (meth) acrylic polymer (A) has a weight average molecular weight (Mw) measured by gel permeation chromatography method (GPC method) in terms of polystyrene, preferably 150,000 to 2.5 million, more preferably 20 It is 10,000 to 2,000,000, more preferably 250,000 to 1,500,000.
  • Mw weight average molecular weight measured by gel permeation chromatography method
  • GPC method gel permeation chromatography method
  • the (meth) acrylic polymer (A) has an Mw / Mn measured by the GPC method of preferably 12.0 or less, more preferably 9.0 or less, and even more preferably 6.0 or less. It is preferable from the viewpoint of improving durability that Mw / Mn is within the above range.
  • the monomer component forming the (meth) acrylic polymer (A) is selected from (meth) acrylic acid alkyl esters, (meth) acrylic acid alkoxyalkyl esters and alkoxypolyalkylene glycol mono (meth) acrylates described below. Examples include at least one monomer (a1), a crosslinkable group-containing monomer (a2), and other monomers (a3). Hereinafter, these are also simply referred to as “monomers (a1) to (a3)”.
  • the monomer (a1) is represented by, for example, the formula (a-1).
  • CH 2 CR 1 -COOR 2 (a-1)
  • R 1 is a hydrogen atom or a methyl group
  • R 2 is a group represented by the formula (g-1).
  • R 4 (g-1) R 3 is an alkylene group
  • R 4 is an alkyl group
  • n is an integer of 0 or more.
  • the alkylene group preferably has 1 to 10 carbon atoms, more preferably 1 to 5 carbon atoms.
  • the number of carbon atoms of the alkyl group is preferably 1 to 24, more preferably 1 to 10.
  • n is preferably 0 to 20, more preferably 0 to 4, and still more preferably 0 to 2.
  • (meth) acrylic acid alkyl esters examples include methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, and isobutyl (meth).
  • Examples of (meth) acrylic acid alkoxyalkyl esters include methoxymethyl (meth) acrylate, 2-methoxyethyl (meth) acrylate, 2-ethoxyethyl (meth) acrylate, 3-methoxypropyl (meth) acrylate, and 3-ethoxy.
  • Examples thereof include propyl (meth) acrylate, 4-methoxybutyl (meth) acrylate, and 4-ethoxybutyl (meth) acrylate.
  • alkoxypolyalkylene glycol mono (meth) acrylate examples include methoxydiethylene glycol mono (meth) acrylate, methoxydipropylene glycol mono (meth) acrylate, ethoxytriethylene glycol mono (meth) acrylate, ethoxydiethylene glycol mono (meth) acrylate, And methoxytriethylene glycol mono (meth) acrylate.
  • a monomer (a1) may be used individually by 1 type, and may use 2 or more types.
  • the content of the monomer (a1) is preferably 50% by mass or more, more preferably 65% by mass or more, and still more preferably. 70 to 99% by mass.
  • the content of the monomer (a1) is 50% by mass or more, the pressure-sensitive adhesive layer obtained is excellent in adhesive strength and cohesive strength, which is preferable.
  • the monomer (a2) is a monomer having at least one crosslinkable group.
  • Examples of the crosslinkable group include a hydroxyl group and a carboxyl group.
  • Examples of the monomer (a2) include a carboxyl group-containing (meth) acrylate, an ethylenically unsaturated carboxylic acid, and a hydroxyl group-containing (meth) acrylic monomer.
  • carboxyl group-containing (meth) acrylate examples include ⁇ -carboxyethyl (meth) acrylate, 5-carboxypentyl (meth) acrylate, mono (meth) acryloyloxyethyl ester succinate, ⁇ -carboxypolycaprolactone mono ( And (meth) acrylate.
  • Examples of the ethylenically unsaturated carboxylic acid include (meth) acrylic acid, crotonic acid, maleic acid, fumaric acid, itaconic acid, and citraconic acid.
  • hydroxyl group-containing (meth) acrylic monomer examples include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 6-hydroxyhexyl (meth) acrylate, And hydroxyl group-containing (meth) acrylates such as 8-hydroxyoctyl (meth) acrylate.
  • a monomer (a2) may be used individually by 1 type, and may use 2 or more types.
  • the content of the monomer (a2) is from the viewpoint of forming an appropriate crosslinked structure with the crosslinking agent (C) described later.
  • the content is preferably 0.1 to 15% by mass, more preferably 0.3 to 10% by mass, and still more preferably 0.5 to 8% by mass.
  • the monomer (a3) is a monomer other than the monomers (a1) and (a2).
  • Examples of the monomer (a3) include (meth) acrylic monomers and vinyl group-containing monomers.
  • Examples of the (meth) acrylic monomer include alicyclic group-containing (meth) acrylic acid esters such as (meth) acrylic acid cycloalkyl esters, (meth) acrylic acid aryl esters, (meth) acrylic acid aralkyl esters, ( Amino group-containing (meth) acrylic ester such as (meth) acrylic acid aryloxyalkyl ester, (meth) acrylic acid aminoalkyl ester, glycidyl group-containing (meth) acrylic monomer, isocyanate group-containing (meth) acrylic monomer, amide Examples thereof include group-containing (meth) acrylic monomers and cyano group-containing (meth) acrylic monomers.
  • Examples of alicyclic group-containing (meth) acrylic acid esters, (meth) acrylic acid aryl esters, and (meth) acrylic acid aralkyl esters include cyclohexyl (meth) acrylate, 4-tert-butylcyclohexyl (meth) acrylate, and isobornyl. (Meth) acrylate, phenyl (meth) acrylate, and benzyl (meth) acrylate may be mentioned.
  • Examples of (meth) acrylic acid aryloxyalkyl esters include phenoxymethyl (meth) acrylate, 2-phenoxyethyl (meth) acrylate, 2-tolyloxyethyl (meth) acrylate, xylyloxymethyl (meth) acrylate, and naphthyl.
  • An oxymethyl (meth) acrylate is mentioned.
  • amino group-containing (meth) acrylic acid ester examples include dimethylaminoethyl (meth) acrylate and diethylaminoethyl (meth) acrylate.
  • Examples of the glycidyl group-containing (meth) acrylic monomer and the isocyanate group-containing (meth) acrylic monomer include glycidyl (meth) acrylate and 2-isocyanatoethyl (meth) acrylate.
  • amide group-containing (meth) acrylic monomers examples include (meth) acrylamide, N-methyl (meth) acrylamide, N-ethyl (meth) acrylamide, N-propyl (meth) acrylamide, and N-hexyl (meth) acrylamide. Is mentioned.
  • cyano group-containing (meth) acrylic monomer examples include alkyl cyanoacrylate and (meth) acrylonitrile.
  • vinyl group-containing monomer examples include vinyl esters such as vinyl acetate and vinyl propionate; olefins such as ethylene, propylene and isobutylene; halogenated olefins such as vinyl chloride and vinylidene chloride; styrenes such as styrene and ⁇ -methylstyrene.
  • Monomer; Diene monomers such as butadiene, isoprene, chloroprene, etc. may be mentioned.
  • a monomer (a3) may be used individually by 1 type, and may use 2 or more types.
  • the (meth) acrylic oligomer (B) has a hydrolyzable silyl group, Mw of 500 to 30,000, and Tg of 0 ° C. or higher.
  • the (meth) acrylic oligomer (B) has a relatively high Tg, the surface strength of the pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition containing the (B) can be increased, and high temperature and high It becomes possible to prevent the pressure-sensitive adhesive layer from being adhered or peeled off from the adherend after being placed under wet conditions.
  • the hydrolyzable silyl group can improve the durability of the pressure-sensitive adhesive layer, particularly when a glass plate is used as an adherend, under high temperature and high humidity conditions. Unlike conventional methods in which a silane coupling agent is added to the pressure-sensitive adhesive composition, it is not hindered by a polymer having a Tg, which has a high effect of improving durability by hydrolyzable silyl groups. It is considered that a pressure-sensitive adhesive layer having excellent durability under conditions can be obtained.
  • (Meth) acrylic oligomer (B) can also be used as a tackifier.
  • the tackifier consisting of (B) can form a pressure-sensitive adhesive layer excellent in durability under high temperature and high humidity conditions by being blended with the pressure-sensitive adhesive composition.
  • hydrolyzable silyl group (B) examples include a group represented by the formula (B-1).
  • R 5 is an alkyl group having 1 to 12 carbon atoms
  • R 6 is an alkylene group having 1 to 4 carbon atoms
  • R 7 is an alkyl group having 1 to 12 carbon atoms.
  • n is an integer from 0 to 2
  • m is an integer from 0 to 4. * Represents a bond.
  • Examples of the group represented by the formula (B-1) include a trimethoxysilyl group, a triethoxysilyl group, a methyldimethoxysilyl group, a methyldiethoxysilyl group, and a tris (2-methoxyethoxy) silyl group.
  • the Mw measured by the GPC method is a polystyrene conversion value of 500 to 30,000, preferably 1,000 to 20,000, more preferably 1,500 to 10,000. It is preferable from the viewpoint of compatibility with the (meth) acrylic polymer (A) that Mw is within the above range. Moreover, when Mw is equal to or higher than the lower limit value, a sufficiently high Tg is easily obtained, and when Mw is equal to or lower than the upper limit value, it is easily compatible with the (meth) acrylic polymer (A). It becomes difficult to cause problems such as generation and deterioration of durability. If the Mw is less than 500, a sufficiently high Tg cannot be obtained.
  • the (meth) acrylic oligomer (B) has an Mw / Mn measured by the GPC method of preferably 7 or less, more preferably 5 or less, and even more preferably 3 or less.
  • Mw / Mn measured by the GPC method of preferably 7 or less, more preferably 5 or less, and even more preferably 3 or less.
  • Tg of the (meth) acrylic oligomer (B) can be measured, for example, by a differential scanning calorimeter by the method described in the examples.
  • the Tg of the (meth) acrylic oligomer (B) is 0 ° C. or higher, preferably 10 to 120 ° C., more preferably 20 to 100 ° C. It is preferable that Tg is within the above range because the pressure-sensitive adhesive layer obtained from the pressure-sensitive adhesive composition is excellent in durability under high temperature and high humidity conditions.
  • the content of the (meth) acrylic oligomer (B) is preferably 0.5 to 20 parts by mass with respect to 100 parts by mass of the (meth) acrylic polymer (A).
  • the amount is more preferably 1 to 15 parts by mass, still more preferably 2 to 10 parts by mass.
  • the content of (B) is equal to or higher than the lower limit value, an effect of improving durability can be imparted to the pressure-sensitive adhesive layer.
  • the adhesive layer becomes cloudy or the Tg of the pressure-sensitive adhesive layer. It is hard to produce the malfunction that adhesive force falls because it becomes too high.
  • (meth) acrylic oligomer (B) for example, (meth) acrylic oligomer (B1) having a hydrolyzable silyl group at the end of the molecule (hereinafter also referred to as “oligomer (B1)”), hydrolysis.
  • (Meth) acrylic oligomer (B2) (hereinafter also referred to as “oligomer (B2)”) which is an oligomer of a monomer component containing a polymerizable silyl group-containing monomer.
  • the oligomer (B1) has a hydrolyzable silyl group at the end of the molecule.
  • the oligomer (B1) is preferably produced by polymerizing a monomer component in the presence of a hydrolyzable silyl group-containing chain transfer agent. By using the chain transfer agent, an oligomer (B1) having a hydrolyzable silyl group at the end of the molecule is obtained.
  • the pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition containing the oligomer (B1) is very excellent in durability under high temperature and high humidity conditions. Further, the pressure-sensitive adhesive layer is preferable because it has good adhesive strength, and particularly has high adhesive strength after standing under high temperature and high humidity conditions.
  • the Tg of the oligomer (B1) is preferably 0 ° C. or higher. Therefore, it is preferable to use at least a monomer having a Tg of the homopolymer of 0 ° C. or higher as the monomer component.
  • Examples of the monomer having a homopolymer Tg of 0 ° C. or higher include (meth) acrylic acid alkyl ester, (meth) acrylic acid alkoxyalkyl ester, and alicyclic group-containing (meth) acrylic acid having a Tg of 0 ° C. or higher. Ester, aryl group-containing (meth) acrylic acid ester, carboxyl group-containing (meth) acrylate, ethylenically unsaturated carboxylic acid, amino group-containing (meth) acrylic acid ester, amide group-containing (meth) acrylic monomer, cyano group-containing (Meth) acrylic monomers and vinyl group-containing monomers.
  • (Meth) acrylic acid alkyl esters such as meth) acrylate
  • (meth) acrylic acid alkoxyalkyl esters such as ethoxyethyl methacrylate
  • Aryl group-containing (meth) acrylic acid esters such as carboxyethyl acrylate and other carboxyl group-containing (meth) acrylates; (meth) acrylic acid, maleic acid, itaconic acid and other ethylenically unsaturated carboxylic acids; dimethylaminoethyl (meta ) Amino group-containing (meth) acrylic acid esters such as acrylates; Amide group-containing (meth) acrylic monomers such as acrylamide and dimethylacrylamide; Cyano group-containing (meth) acrylic monomers such as acrylonitrile; Vinyl acetates, vinyls such as styrene And group-containing monomers.
  • alicyclic group-containing (meth) acrylic acid esters are preferable from the viewpoint of easily obtaining an oligomer (B) having a Mw of 30,000 or less and having a high Tg.
  • Tg of the homopolymer a value described in Polymer Handbook Fourth Edition (Wiley-Interscience 2003) or a manufacturer's catalog can be used.
  • the content of the monomer whose Tg of the homopolymer is 0 ° C. or more is preferably from the viewpoint of setting the Tg of the oligomer (B1) within the above range in 100% by mass of the monomer component used to form the oligomer (B1). Is 10% by mass or more, more preferably 30% by mass or more, and still more preferably 50% by mass or more.
  • Examples of the monomer component used to form the oligomer (B1) include the above-mentioned ⁇ (meth) acrylic acid alkyl ester, (meth) acrylic acid other than the monomer having a Tg of 0 ° C. or higher.
  • ⁇ (meth) acrylic acid alkyl ester (meth) acrylic acid other than the monomer having a Tg of 0 ° C. or higher.
  • ⁇ crosslinkable group-containing monomer (a2) >> and ⁇ other monomers (a3) >>
  • Monomers can also be used.
  • the hydrolyzable silyl group containing monomer as described in the column of ⁇ Oligomer (B2)> can also be used.
  • the oligomer (B2) is a polymer of monomer components including a hydrolyzable silyl group-containing monomer. Since the oligomer (B2) has a structural unit derived from a hydrolyzable silyl group-containing monomer, the pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition containing the oligomer (B2) is durable under high temperature and high humidity conditions. Good properties.
  • hydrolyzable silyl group-containing monomer examples include a hydrolyzable silyl group-containing (meth) acrylic monomer represented by the formula (B2-1) and a hydrolyzable silyl group-containing monomer represented by the formula (B2-2) A vinyl monomer is mentioned.
  • R 8 is a hydrogen atom or a methyl group
  • R 9 is an alkylene group having 1 to 12 carbon atoms
  • R (B-1) is represented by the formula (B-1). Group.
  • R 10 is a direct bond or an alkylene group having 1 to 12 carbon atoms
  • R (B-1) is a group represented by the formula (B-1).
  • hydrolyzable silyl group-containing (meth) acrylic monomers examples include 3- (meth) acryloxypropylmethyldimethoxysilane, 3- (meth) acryloxypropylmethyldiethoxysilane, and 3- (meth) acryloxypropyl.
  • hydrolyzable silyl group-containing (meth) acrylic monomers examples include trimethoxysilane, 3- (meth) acryloxypropyltriethoxysilane, and 3- (meth) acryloxyoctyltrimethoxysilane.
  • hydrolyzable silyl group-containing vinyl monomer examples include vinyltrimethoxysilane, vinyltriethoxysilane, octenyltrimethoxysilane, and vinyltris (2-methoxyethoxy) silane.
  • One hydrolyzable silyl group-containing monomer may be used alone, or two or more hydrolyzable silyl group-containing monomers may be used.
  • the content of the hydrolyzable silyl group-containing monomer is preferably 1 to 90% by mass, more preferably 3 to 50% by mass, and still more preferably 100% by mass of the monomer component used to form the oligomer (B2). 4 to 30% by mass. It is preferable that the content of the hydrolyzable silyl group-containing monomer is within the above range because of excellent compatibility and durability under high temperature and high humidity conditions.
  • the Tg of the oligomer (B2) is preferably 0 ° C. or higher. Therefore, it is preferable to use at least a monomer having a Tg of the homopolymer of 0 ° C. or higher as the monomer component.
  • Examples of the monomer having a Tg of the homopolymer of 0 ° C. or higher include monomers described in the section ⁇ Oligomer (B1)>.
  • the content of the monomer whose Tg of the homopolymer is 0 ° C. or higher is preferably from the viewpoint of setting the Tg of the oligomer (B2) within the above range in 100% by mass of the monomer component used to form the oligomer (B2). Is 10% by mass or more, more preferably 30% by mass or more, and still more preferably 50% by mass or more.
  • Examples of the monomer component used to form the oligomer (B2) include, in addition to the above-mentioned hydrolyzable silyl group-containing monomer and the monomer having a Tg of 0 ° C. or higher, the above-mentioned ⁇ (meth) acrylic acid At least one monomer (a1) selected from alkyl ester, alkoxyalkyl ester of (meth) acrylic acid and alkoxypolyalkylene glycol mono (meth) acrylate, ⁇ crosslinkable group-containing monomer (a2) >> and ⁇ other monomers ( a3) >> can also be used.
  • the (meth) acrylic polymer (A) and the (meth) acrylic oligomer (B) are produced by a conventionally known polymerization method such as a solution polymerization method, a bulk polymerization method, an emulsion polymerization method, or a suspension polymerization method. Among these, the solution polymerization method is preferable.
  • a monomer component and, if necessary, a chain transfer agent, a polymerization solvent, and the like are charged in a reaction vessel.
  • a polymerization initiator is added under an inert gas atmosphere such as nitrogen gas, and the reaction start temperature is set.
  • the reaction system is maintained at a temperature of usually 40 to 100 ° C., preferably 50 to 80 ° C., usually 50 to 90 ° C., preferably 60 to 90 ° C., and allowed to react for 2 to 20 hours.
  • chain transfer agent examples include hydrolyzable silyl group-containing chain transfer agents and other chain transfer agents.
  • chain transfer agent In the production of the oligomer (B1), it is preferable to use a hydrolyzable silyl group-containing chain transfer agent.
  • the hydrolyzable silyl group-containing chain transfer agent is represented, for example, by the formula (B1-1).
  • HS-R 11 -R (B-1) (B1-1) In the formula (B1-1), R 11 is an alkylene group having 1 to 12 carbon atoms, and R (B-1) is a group represented by the formula (B-1).
  • Examples of the chain transfer agent represented by the formula (B1-1) include 3-mercaptopropyltrimethoxysilane and 3-mercaptopropylmethyldimethoxysilane.
  • chain transfer agents examples include monofunctional thiols such as n-dodecyl mercaptan, polyfunctional thiols such as pentaerythritol tetrakis (3-mercaptopropionate), ⁇ -methylstyrene dimer (2,4-diphenyl). Styrene dimers such as -4-methyl-1-pentene) and quinoexters.
  • monofunctional thiols such as n-dodecyl mercaptan
  • polyfunctional thiols such as pentaerythritol tetrakis (3-mercaptopropionate)
  • ⁇ -methylstyrene dimer (2,4-diphenyl).
  • Styrene dimers such as -4-methyl-1-pentene
  • quinoexters examples include 2-butylene glycol, 2,4-diphenyl.
  • “Kino Exter” is a trade name of Kawasaki Kasei Kogy
  • a chain transfer agent may be used individually by 1 type, and may use 2 or more types.
  • the chain transfer agent is preferably 0.1 to 40 parts by weight, more preferably 1 to 20 parts by weight, still more preferably 5 to 15 parts by weight based on 100 parts by weight of the monomer component used to form the oligomer (B). Used in amounts in the range of parts by weight.
  • Examples of the polymerization initiator include azo initiators and peroxide polymerization initiators.
  • Examples of the azo initiator include 2,2′-azobisisobutyronitrile, 2,2′-azobis (4-methoxy-2,4-dimethylvaleronitrile), 2,2′-azobis (2- Cyclopropylpropionitrile), 2,2′-azobis (2,4-dimethylvaleronitrile), 2,2′-azobis (2-methylbutyronitrile), 1,1′-azobis (cyclohexane-1-carbohydrate) Nitrile), 2- (carbamoylazo) isobutyronitrile, 2-phenylazo-4-methoxy-2,4-dimethylvaleronitrile, 2,2′-azobis (2-amidinopropane) dihydrochloride, 2,2′- Azobis (N, N'-dimethyleneisobutylamidine), 2,2'-azobis [2-methyl-N- (2-hydroxyethyl)
  • peroxide polymerization initiators examples include t-butyl hydroperoxide, cumene hydroxide, dicumyl peroxide, benzoyl peroxide, lauroyl peroxide, caproyl peroxide, and di-i-propyl peroxydicarbonate.
  • a polymerization initiator may be used individually by 1 type, and may use 2 or more types.
  • the polymerization initiator is usually 0.001 to 5 parts by weight, preferably 100 parts by weight, preferably 100 parts by weight of the monomer component used to form the (A). Used in an amount in the range of 0.005 to 3 parts by mass.
  • the polymerization initiator is preferably 0.1 to 2.0 parts by mass with respect to 100 parts by mass of the monomer component used to form the (B). More preferably, it is used in an amount in the range of 0.2 to 1.0 part by mass.
  • polymerization solvent used for the solution polymerization examples include aromatic hydrocarbons such as benzene, toluene and xylene; aliphatic hydrocarbons such as n-pentane, n-hexane, n-heptane and n-octane; cyclopentane, cyclohexane, Cycloaliphatic hydrocarbons such as cycloheptane and cyclooctane; ethers such as diethyl ether, diisopropyl ether, 1,2-dimethoxyethane, dibutyl ether, tetrahydrofuran, dioxane, anisole, phenylethyl ether, diphenyl ether; chloroform, carbon tetrachloride, Halogenated hydrocarbons such as 1,2-dichloroethane and chlorobenzene; esters such as ethyl acetate, propyl acetate, butyl a
  • a polymerization solvent may be used individually by 1 type, and may use 2 or more types. Moreover, you may add suitably a polymerization initiator, a chain transfer agent, a monomer component, and a polymerization solvent during a polymerization reaction.
  • the pressure-sensitive adhesive composition of the present invention preferably contains a crosslinking agent (C).
  • the crosslinking agent (C) is appropriately selected depending on the crosslinkable group that can be introduced into the (meth) acrylic polymer (A), and for example, an isocyanate compound, an epoxy compound, or a metal chelate compound can be used.
  • a crosslinking agent (C) By crosslinking the (meth) acrylic polymer (A) with the crosslinking agent (C), a crosslinked body (network polymer) can be formed, and an adhesive layer having excellent heat resistance can be obtained.
  • a crosslinking agent (C) may be used individually by 1 type, and may use 2 or more types.
  • the content of the crosslinking agent (C) is preferably 0.1 to 20 parts by mass, more preferably 0, relative to 100 parts by mass of the (meth) acrylic polymer (A). 1 to 12 parts by mass, more preferably 0.2 to 4 parts by mass.
  • an isocyanate compound having 2 or more isocyanate groups in one molecule is usually used, preferably 2 to 8, and more preferably 3 to 6.
  • the number of isocyanate groups is within the above range, it is preferable from the viewpoint of the crosslinking reaction efficiency between the (meth) acrylic polymer (A) and the isocyanate compound and the flexibility of the pressure-sensitive adhesive layer.
  • diisocyanate compound having 2 isocyanate groups in one molecule examples include aliphatic diisocyanate, alicyclic diisocyanate, and aromatic diisocyanate.
  • Aliphatic diisocyanates include ethylene diisocyanate, tetramethylene diisocyanate, pentamethylene diisocyanate, hexamethylene diisocyanate, 2-methyl-1,5-pentane diisocyanate, 3-methyl-1,5-pentane diisocyanate, 2,2,4-trimethyl
  • aliphatic diisocyanates having 4 to 30 carbon atoms such as -1,6-hexamethylene diisocyanate.
  • alicyclic diisocyanate examples include 7 to 30 carbon atoms such as isophorone diisocyanate, cyclopentyl diisocyanate, cyclohexyl diisocyanate, hydrogenated xylylene diisocyanate, hydrogenated tolylene diisocyanate, hydrogenated diphenylmethane diisocyanate, and hydrogenated tetramethylxylene diisocyanate.
  • Diisocyanate is mentioned.
  • aromatic diisocyanate examples include aromatic diisocyanates having 8 to 30 carbon atoms such as phenylene diisocyanate, tolylene diisocyanate, xylylene diisocyanate, naphthylene diisocyanate, diphenyl ether diisocyanate, diphenylmethane diisocyanate, and diphenylpropane diisocyanate.
  • isocyanate compound having 3 or more isocyanate groups in one molecule examples include aromatic polyisocyanate, aliphatic polyisocyanate, and alicyclic polyisocyanate. Specific examples include 2,4,6-triisocyanate toluene, 1,3,5-triisocyanate benzene, and 4,4 ', 4 "-triphenylmethane triisocyanate.
  • Examples of the isocyanate compound include multimers (for example, dimers or trimers, biurets, and isocyanurates) and derivatives (for example, polyhydric alcohols) of the above isocyanate compounds having 2 or 3 isocyanate groups. Addition reaction product with two or more diisocyanate compounds) and polymer.
  • Examples of the polyhydric alcohol in the derivative include trivalent or higher alcohols such as trimethylolpropane, glycerin and pentaerythritol as low molecular weight polyhydric alcohols; high molecular weight polyhydric alcohols such as polyether polyols, Examples include polyester polyol, acrylic polyol, polybutadiene polyol, and polyisoprene polyol.
  • isocyanate compounds include diphenylmethane diisocyanate trimer, polymethylene polyphenyl polyisocyanate, hexamethylene diisocyanate or tolylene diisocyanate biuret or isocyanurate, trimethylolpropane and tolylene diisocyanate or xylylene diisocyanate.
  • Reaction product for example, a trimolecular adduct of tolylene diisocyanate or xylylene diisocyanate
  • reaction product of trimethylolpropane and hexamethylene diisocyanate for example, a trimolecular adduct of hexamethylene diisocyanate
  • polyether polyisocyanate for example, a polyether polyisocyanate
  • Polyester polyisocyanate is mentioned.
  • xylylene diisocyanate-based and tolylene diisocyanate-based crosslinking agents are preferable from the viewpoint of difficult yellowing.
  • Examples of the epoxy compound include compounds having two or more epoxy groups in the molecule.
  • ethylene glycol diglycidyl ether polyethylene glycol diglycidyl ether, glycerin diglycidyl ether, glycerin triglycidyl ether, 1,6-hexane.
  • an alkoxide, acetylacetone, ethyl acetoacetate or the like is coordinated to a polyvalent metal such as aluminum, iron, copper, zinc, tin, titanium, nickel, antimony, magnesium, vanadium, chromium, and zirconium.
  • a polyvalent metal such as aluminum, iron, copper, zinc, tin, titanium, nickel, antimony, magnesium, vanadium, chromium, and zirconium.
  • Compounds. Specific examples include aluminum isopropylate, aluminum secondary butyrate, aluminum ethyl acetoacetate / diisopropylate, aluminum trisethyl acetoacetate, and aluminum trisacetylacetonate.
  • the pressure-sensitive adhesive composition of the present invention includes, in addition to the above components, a silane coupling agent, an antistatic agent, an antioxidant, a light stabilizer, a metal corrosion inhibitor, and (B) as long as the effects of the present invention are not impaired.
  • a silane coupling agent an antistatic agent, an antioxidant, a light stabilizer, a metal corrosion inhibitor, and (B) as long as the effects of the present invention are not impaired.
  • the pressure-sensitive adhesive composition of the present invention preferably contains an organic solvent (E) in order to adjust its applicability.
  • organic solvent (E) include the polymerization solvents described in the section ⁇ Production conditions for (meth) acrylic polymer (A) and (meth) acrylic oligomer (B) >>.
  • the content of the organic solvent is usually 30 to 90% by mass, preferably 40 to 90% by mass.
  • solid content refers to all components excluding the organic solvent (E) among the components contained in the pressure-sensitive adhesive composition
  • solid content concentration refers to the pressure-sensitive adhesive composition 100.
  • the ratio of the said solid content with respect to the mass% is said.
  • the total amount of the (meth) acrylic polymer (A) and the (meth) acrylic oligomer (B) is usually 80% by mass or more, preferably 90% by mass in a solid content of 100% by mass. % Or more, more preferably 95% by mass or more.
  • the upper limit of the total amount can be appropriately determined depending on the amount of other components such as the crosslinking agent (C).
  • the (meth) acrylic polymer (A), the (meth) acrylic oligomer (B), and other components as necessary are mixed by a conventionally known method.
  • a pressure-sensitive adhesive composition can be prepared by mixing a solution containing the (meth) acrylic oligomer (B) and other components as necessary.
  • the monomer component which forms (meth) acrylic-type polymer (A) is added to the solution containing (meth) acrylic-type oligomer (B), polymerization reaction is performed, and other components are added as needed.
  • the pressure-sensitive adhesive composition can also be prepared.
  • the pressure-sensitive adhesive layer is formed from the above-mentioned pressure-sensitive adhesive composition.
  • the pressure-sensitive adhesive layer can be obtained by proceeding with the crosslinking reaction in the above-mentioned pressure-sensitive adhesive composition, specifically, by crosslinking the (meth) acrylic polymer (A) with the crosslinking agent (C).
  • the conditions for forming the pressure-sensitive adhesive layer are, for example, as follows.
  • the pressure-sensitive adhesive composition of the present invention is applied on a support and varies depending on the type of solvent, but is usually 50 to 150 ° C., preferably 60 to 100 ° C., usually 1 to 10 minutes, preferably 2 to 7 minutes. Then, the solvent is removed and a coating film is formed.
  • the film thickness of the dried coating film is usually 5 to 75 ⁇ m, preferably 10 to 50 ⁇ m.
  • the pressure-sensitive adhesive layer is preferably formed under the following conditions. After applying the pressure-sensitive adhesive composition of the present invention on a support and applying a cover film on the coating film formed under the above conditions, usually 3 days or more, preferably 7 to 10 days, usually 5 to 60 ° C., It is preferably cured in an environment of 15 to 40 ° C., usually 30 to 70% RH, preferably 40 to 70% RH. When crosslinking is performed under the aging conditions as described above, a crosslinked body (network polymer) can be efficiently formed.
  • a known thickness such as a spin coating method, a knife coating method, a roll coating method, a bar coating method, a blade coating method, a die coating method, or a gravure coating method may be used.
  • the method of applying and drying can be used.
  • polyester films such as polyethylene terephthalate (PET); plastic films such as polyolefin films such as polyethylene, polypropylene, and ethylene-vinyl acetate copolymer.
  • PET polyethylene terephthalate
  • plastic films such as polyolefin films such as polyethylene, polypropylene, and ethylene-vinyl acetate copolymer.
  • the pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition of the present invention has a gel fraction of preferably 60 to 100% by mass, more preferably from the viewpoints of distortion suppression, cohesive strength, adhesive strength, and removability of the polarizing plate. Is 65 to 95% by mass, more preferably 70 to 90% by mass.
  • the pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition of the present invention is excellent in durability under high temperature and high humidity conditions.
  • the pressure-sensitive adhesive sheet for polarizing plates of the present invention has a pressure-sensitive adhesive layer formed from the above-mentioned pressure-sensitive adhesive composition.
  • the pressure-sensitive adhesive sheet include a double-sided pressure-sensitive adhesive sheet having only the pressure-sensitive adhesive layer, a base material, and a double-sided pressure-sensitive adhesive sheet having the pressure-sensitive adhesive layer formed on both surfaces of the base material, the base material, and one of the base materials.
  • Examples thereof include a single-sided pressure-sensitive adhesive sheet having the above-mentioned pressure-sensitive adhesive layer formed on the surface, and a pressure-sensitive adhesive sheet having a peel-treated cover film attached to the surface of the pressure-sensitive adhesive sheet that is not in contact with the base material.
  • polyester films such as polyethylene terephthalate (PET); plastic films such as polyolefin films such as polyethylene, polypropylene, and ethylene-vinyl acetate copolymer.
  • PET polyethylene terephthalate
  • plastic films such as polyolefin films such as polyethylene, polypropylene, and ethylene-vinyl acetate copolymer.
  • the conditions for forming the pressure-sensitive adhesive layer and the gel fraction are the same as the conditions described in the column [Pressure-sensitive adhesive layer].
  • the thickness of the pressure-sensitive adhesive layer is usually 5 to 75 ⁇ m, preferably 10 to 50 ⁇ m, from the viewpoint of maintaining adhesive performance.
  • the film thickness of the substrate and the cover film is not particularly limited, but is usually 10 to 125 ⁇ m, preferably 25 to 75 ⁇ m.
  • the polarizing plate with an adhesive layer has a polarizing plate and the adhesive layer formed from the adhesive composition of this invention in the at least one surface of the said polarizing plate.
  • polarizing plate is used to include “polarizing film”.
  • polarizing plate a conventionally known polarizing plate can be used, and examples thereof include a polarizing plate having a polarizer and a polarizer protective film disposed on one side or both sides of the polarizer.
  • Examples of the polarizer include a stretched film obtained by adding a polarizing component to a film made of a polyvinyl alcohol resin and stretching the film.
  • Examples of the polyvinyl alcohol-based resin include polyvinyl alcohol, polyvinyl formal, polyvinyl acetal, and a saponified product of an ethylene / vinyl acetate copolymer.
  • Examples of the polarization component include iodine or a dichroic dye.
  • the polarizer protective film examples include films made of cellulose such as triacetyl cellulose and diacetyl cellulose, polycarbonate films, and polyether sulfone films.
  • films made of cellulose such as triacetyl cellulose and diacetyl cellulose, polycarbonate films, and polyether sulfone films.
  • the long-term reliability, specifically, wet heat resistance is excellent.
  • the thickness of the polarizing plate is preferably 30 to 250 ⁇ m, more preferably 50 to 200 ⁇ m.
  • the method for forming the pressure-sensitive adhesive layer on the surface of the polarizing plate is not particularly limited.
  • the method for applying the pressure-sensitive adhesive composition directly on the surface of the polarizing plate using a bar coater and drying and aging, the pressure-sensitive adhesive sheet for polarizing plate of the present invention There is a method in which the pressure-sensitive adhesive layer possessed by is transferred to the polarizing plate surface and aged.
  • the conditions for drying and aging, the gel fraction, and the like are the same as the conditions described in the [Adhesive layer] column.
  • the thickness of the pressure-sensitive adhesive layer formed on the polarizing plate is preferably 5 to 75 ⁇ m, more preferably 10 to 50 ⁇ m in terms of dry film thickness.
  • the adhesive layer should just be formed in at least one surface of a polarizing plate, the aspect in which an adhesive layer is formed only in the single side
  • the layer which has other functions such as a glare-proof layer, a phase difference layer, a viewing angle improvement layer, may be laminated
  • a liquid crystal element is produced by providing the polarizing plate with the pressure-sensitive adhesive layer of the present invention obtained as described above on the substrate surface of the liquid crystal cell.
  • the liquid crystal cell has a structure in which a liquid crystal layer is sandwiched between two substrates.
  • a laminate in which a polarizing plate, a pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition of the present invention, and a glass substrate are laminated in this order can also be produced.
  • substrate which a liquid crystal cell has glass plates, such as an alkali glass plate, are mentioned, for example.
  • the thickness of the substrate is preferably 5 mm or less, more preferably 0.05 to 2 mm.
  • the measuring method of physical properties is as follows.
  • Mw weight average molecular weight
  • Mn number average molecular weight
  • HLC-8320GPC manufactured by Tosoh Corporation
  • -GPC column configuration The following four columns (all manufactured by Tosoh Corporation) (1) TSKgel HxL-H (guard column) (2) TSKgel GMHxL (3) TSKgel GMHxL (4) TSKgel G2500HxL ⁇ Flow rate: 1.0 mL / min -Column temperature: 40 ° C Sample concentration: 1.5% (w / v) (diluted with tetrahydrofuran) ⁇ Mobile phase solvent: Tetrahydrofuran ⁇ Standard polystyrene conversion
  • Tg Glass transition temperature
  • Example 1 (1) Preparation of pressure-sensitive adhesive composition
  • the plate was allowed to stand and matured for 7 days under the conditions of RH to obtain a polarizing plate with a pressure-sensitive adhesive layer having a PET film, a pressure-sensitive adhesive layer having a thickness of 20 ⁇ m, and a polarizing plate.
  • Example 2 [Examples 2 to 5 and Comparative Examples 1 to 6]
  • Example 1 the adhesive composition, the adhesive sheet, and the polarizing plate with an adhesive layer were obtained like Example 1 except having changed the compounding composition as described in Table 2.
  • a polarizing plate with a pressure-sensitive adhesive layer obtained in Examples and Comparative Examples (a laminate comprising PET film / pressure-sensitive adhesive layer / polarizing plate) was cut into a size of 150 mm ⁇ 250 mm to prepare a test piece.
  • the PET film is peeled off from the test piece, and the laminate composed of the pressure-sensitive adhesive layer / polarizing plate is pasted on one side of the 2 mm-thick alkali glass plate using a laminator roll so that the pressure-sensitive adhesive layer and the alkali glass plate are in contact with each other. I wore it.
  • the obtained laminate was held in an autoclave adjusted to 50 ° C./5 atm for 20 minutes to prepare a test plate.
  • test plate was left in an environment of 60 ° C./90% RH for 500 hours. Appearance defects such as foaming from the pressure-sensitive adhesive layer of the test plate, cracks in the test plate, and peeling of the pressure-sensitive adhesive layer were visually observed and evaluated according to the following criteria.
  • a polarizing plate with a pressure-sensitive adhesive layer (a laminate comprising PET film / pressure-sensitive adhesive layer / polarizing plate) obtained in Examples and Comparative Examples was cut into a size of 25 mm ⁇ 70 mm to prepare a test piece.
  • the PET film is peeled off from the test piece, and the laminate composed of the pressure-sensitive adhesive layer / polarizing plate is pasted on one side of the 2 mm-thick alkali glass plate using a laminator roll so that the pressure-sensitive adhesive layer and the alkali glass plate are in contact with each other. I wore it.
  • the obtained laminate was held in an autoclave adjusted to 50 ° C./5 atm for 20 minutes to prepare a test plate. Two similar test plates were prepared for each polarizing plate with an adhesive layer.
  • One test plate was allowed to stand for 30 minutes in an atmosphere of 23 ° C./50% RH. Thereafter, a peeling test was performed with a tensile tester at a peeling rate of 300 mm / min and 90 ° peeling, and the obtained adhesion strength value was defined as an initial adhesive strength.
  • the other test plate was stored in a 60 ° C./95% RH atmosphere for 100 hours and then allowed to stand in a 23 ° C./50% RH atmosphere for 48 hours. Thereafter, a peeling test was performed with a tensile tester at a peeling rate of 300 mm / min and 90 ° peeling, and the obtained adhesion strength value was defined as an adhesive strength after heat and moisture resistance.
  • TD-75 Xylene diisocyanate crosslinking agent (manufactured by Soken Chemical Co., Ltd., trade name)
  • A-50 Silane coupling (SiC) agent (manufactured by Soken Chemical Co., Ltd., trade name)

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Adhesive Tapes (AREA)
  • Laminated Bodies (AREA)

Abstract

Le problème abordé par la présente invention est de pourvoir à une composition adhésive capable de former une couche adhésive qui manifeste une excellente durabilité dans des conditions de température et d'humidité élevées. La solution selon l'invention porte sur une composition adhésive qui contient : un polymère (méth)acrylique ayant une température de transition vitreuse (Tg) inférieure à 0 °C et (B) un oligomère (méth)acrylique ayant un groupe silyle hydrolysable, un poids moléculaire moyen en poids (Mw) de 500 à 30 000 et une Tg de 0 °C ou plus.
PCT/JP2016/083901 2015-12-10 2016-11-16 Composition adhésive, son procédé de production, feuille adhésive, plaque polarisante pourvue d'une couche adhésive, et stratifié WO2017098870A1 (fr)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2019038946A (ja) * 2017-08-25 2019-03-14 王子ホールディングス株式会社 粘着剤組成物、粘着シートおよび積層体
JP2019038947A (ja) * 2017-08-25 2019-03-14 王子ホールディングス株式会社 粘着剤組成物、粘着シートおよび積層体
KR20240035698A (ko) 2022-09-09 2024-03-18 사이덴 가가쿠 가부시키가이샤 점착제 조성물, 점착제층, 점착제층 부착 광학필름, 및 표시장치

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JPH06192642A (ja) * 1992-12-24 1994-07-12 Mitsui Toatsu Chem Inc 反応性ホットメルト型感圧接着剤組成物
JP2005082750A (ja) * 2003-09-10 2005-03-31 Cemedine Co Ltd 接着性に優れた硬化性組成物
JP2006249251A (ja) * 2005-03-10 2006-09-21 Sekisui Chem Co Ltd 硬化性組成物、シーリング剤及び接着剤
JP2008101168A (ja) * 2006-10-20 2008-05-01 Saiden Chemical Industry Co Ltd 粘着剤組成物および光学機能性フィルム
WO2009008470A1 (fr) * 2007-07-11 2009-01-15 Soken Chemical & Engineering Co., Ltd. Composition d'adhésif autocollant pour plaques polarisantes et plaque polarisante ayant une couche d'adhésif autocollant
JP2014145023A (ja) * 2013-01-29 2014-08-14 Nitto Denko Corp 多層粘着シート

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JPH05230428A (ja) * 1992-02-21 1993-09-07 Nitto Denko Corp 水分散型感圧接着剤組成物
JPH06192642A (ja) * 1992-12-24 1994-07-12 Mitsui Toatsu Chem Inc 反応性ホットメルト型感圧接着剤組成物
JP2005082750A (ja) * 2003-09-10 2005-03-31 Cemedine Co Ltd 接着性に優れた硬化性組成物
JP2006249251A (ja) * 2005-03-10 2006-09-21 Sekisui Chem Co Ltd 硬化性組成物、シーリング剤及び接着剤
JP2008101168A (ja) * 2006-10-20 2008-05-01 Saiden Chemical Industry Co Ltd 粘着剤組成物および光学機能性フィルム
WO2009008470A1 (fr) * 2007-07-11 2009-01-15 Soken Chemical & Engineering Co., Ltd. Composition d'adhésif autocollant pour plaques polarisantes et plaque polarisante ayant une couche d'adhésif autocollant
JP2014145023A (ja) * 2013-01-29 2014-08-14 Nitto Denko Corp 多層粘着シート

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2019038946A (ja) * 2017-08-25 2019-03-14 王子ホールディングス株式会社 粘着剤組成物、粘着シートおよび積層体
JP2019038947A (ja) * 2017-08-25 2019-03-14 王子ホールディングス株式会社 粘着剤組成物、粘着シートおよび積層体
KR20240035698A (ko) 2022-09-09 2024-03-18 사이덴 가가쿠 가부시키가이샤 점착제 조성물, 점착제층, 점착제층 부착 광학필름, 및 표시장치

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