TW201638275A - Adhesive composition, adhesive layer, adhesive sheet, optical member provided with adhesive layer, and image display device - Google Patents

Abstract

Provided is an adhesive composition for forming an adhesive layer which is excellent in stress relaxation properties and durability, and has a sufficiently low haze value. Further, provided is an adhesive layer formed out of the adhesive composition. Still further, provided are an adhesive sheet containing the adhesive layer, and an optical member provided with the adhesive layer. Still further, provided is an image display device having at least one optical member provided with the adhesive layer. The adhesive component according to the present invention contains a (meth)acrylic polymer and a polyrotaxane that has a cyclic molecule, a linear molecule threaded through the opening of the cyclic molecule, and blocking groups arranged at both ends of the linear molecule to prevent dislocation of the cyclic molecule from the linear molecule. The (meth)acrylic polymer contains a structural unit derived from a monomer having no aromatic ring structure and also contains a structural unit derived from a monomer having an aromatic ring structure.

Description

Adhesive composition, adhesive layer, adhesive sheet, optical member with adhesive layer, and image display device

This invention relates to an adhesive composition. Further, the present invention relates to an adhesive layer comprising the adhesive composition, an adhesive sheet comprising the adhesive layer, and an optical member having an adhesive layer. Further, the present invention relates to an image display apparatus comprising at least one such optical member with an adhesive layer.

An adhesive composition containing a specific polyrotaxane is reported as an adhesive composition constituting an adhesive layer having excellent stress relaxation properties and durability (Patent Document 1). The specific polyrotaxane is a special polymer known as "SeRM (registered trademark) super polymer" which is known as a slide-ring material of Advanced Soft Materials Co., Ltd., and has a cyclic molecule, a linear molecule that penetrates the opening of the cyclic molecule, and a polyrotaxane that is disposed at a blocking group at both ends of the linear molecule so that the cyclic molecule does not detach from the linear molecule .

In the case where an adhesive layer containing an adhesive composition containing such a specific polyrotaxane is applied to an optical member, in order not to lower the optical characteristics of the optical member, it is required to lower the haze value of the adhesive layer. .

For such a request, there are reports of an adhesive containing a (meth) acrylate-based polymer having no carboxyl group and a (meth) acrylate-based polymer having a carboxyl group in addition to the specific polyrotaxane as described above. A composition (Patent Document 2); and an adhesive composition containing a chelating compound in addition to the specific polyrotaxane as described above (Patent Document 3).

However, in the adhesive composition reported in Patent Document 2 or Patent Document 3, the haze value of the adhesive layer containing the adhesive composition cannot be sufficiently lowered. In Patent Document 2, in the 25 examples, the haze value is 1.0 or more, the haze value is 1.0 or more, the haze value is 1.5 or more, and the haze value is 2.0 or more. Said that the effect is sufficient. In Patent Document 3, in the twenty-first embodiment, the haze value is 1.0 or more, and the haze value is 1.0 or more, and the haze value is 1.5 or more. It cannot be said that the effect is sufficient.

Further, in the adhesive composition reported in Patent Document 2 or 3, the newly added component for suppressing the haze does not participate in the cross-linking formation of the adhesive layer, and thus there is a possibility that the following problems occur: gel fraction The rate is not sufficiently increased, or the added components ooze out to the surface of the adhesive layer to affect the adhesive properties.

[Previous Technical Literature] [Patent Literature]

[Patent Document 1] Japanese Patent Laid-Open Publication No. 2007-224133

[Patent Document 2] Japanese Patent Laid-Open Publication No. 2013-056962

[Patent Document 3] Japanese Patent Laid-Open Publication No. 2013-203854

An object of the present invention is to provide an adhesive composition which is excellent in stress relaxation property and durability and which can exhibit a sufficiently low haze value. Further, an adhesive layer comprising such an adhesive composition is provided. Further, an adhesive sheet comprising such an adhesive layer and an optical member with an adhesive layer are provided. Further, an image display device including at least one such optical member with an adhesive layer can be provided.

The adhesive composition of the present invention contains a (meth)acrylic polymer and a polyrotaxane, and the polyrotaxane has a cyclic molecule and a linear component penetrating through an opening of the cyclic molecule. And a blocking group disposed at both ends of the linear molecule so that the cyclic molecule does not detach from the linear molecule, The (meth)acrylic polymer includes a structural unit derived from a monomer having no aromatic ring structure, and a structural unit derived from a monomer having an aromatic ring structure.

In a preferred embodiment, the content ratio of the (meth)acrylic polymer in the adhesive composition is 70% by weight to 99.9% by weight based on the weight ratio.

In a preferred embodiment, the content ratio of the polyrotaxane in the adhesive composition is from 0.1% by weight to 30% by weight based on the weight ratio.

In a preferred embodiment, the content ratio of the structural unit derived from the monomer having an aromatic ring structure in the (meth)acrylic polymer is from 1% by weight to 35% by weight based on the weight ratio.

In a preferred embodiment, the monomer having an aromatic ring structure contains at least one selected from the group consisting of benzyl acrylate and phenoxyethyl acrylate.

The adhesive layer of the present invention comprises the adhesive composition of the present invention.

The adhesive sheet of the present invention comprises the adhesive layer and the substrate layer of the present invention.

The optical member with an adhesive layer of the present invention comprises the adhesive layer of the present invention and an optical member.

The image display device of the present invention comprises at least one optical member of the present invention with an adhesive layer.

According to the present invention, it is possible to provide an adhesive composition which is excellent in stress relaxation property and durability and which can exhibit a sufficiently low haze value. Further, an adhesive layer comprising such an adhesive composition can be provided. Further, an adhesive sheet comprising such an adhesive layer and an optical member with an adhesive layer can be provided. Further, an image display device including at least one such optical member with an adhesive layer can be provided.

≪Adhesive composition≫

The adhesive composition of the present invention contains a (meth)acrylic polymer and a polyrotaxane, and the polyrotaxane has a cyclic molecule, a linear molecule penetrating the opening of the cyclic molecule, and the ring A blocking group which is disposed at both ends of the linear molecule in such a manner that the molecule does not detach from the linear molecule. Hereinafter, in the present specification, the (meth)acrylic polymer contained in the adhesive composition of the present invention is simply referred to as "(meth)acrylic polymer", and the adhesive composition of the present invention is used. The above polyrotaxane is simply referred to as "polyrotaxane".

In the present specification, the "(meth)acrylic group" means an acryl group and/or a methacryl group, and the "(meth)acrylate" means an acrylate and/or a methacrylate, and so-called "( The "methyl) acrylonitrile group means an acryl fluorenyl group and/or a methacryl fluorenyl group.

The content ratio of the (meth)acrylic polymer in the adhesive composition of the present invention is preferably 70% by weight to 99.9% by weight, more preferably 75% by weight to 99.5% by weight, and still more preferably 80% by weight. It is preferably from 5% by weight to 99% by weight, particularly preferably from 85% by weight to 99% by weight. By adjusting the content ratio of the (meth)acrylic polymer in the adhesive composition of the present invention to the above range, it is possible to provide a haze which is more excellent in stress relaxation property and durability and which can exhibit further sufficiently low haze. The adhesive composition of the adhesive layer of the value, and an adhesive layer comprising the adhesive composition, an adhesive sheet comprising the adhesive layer, and an optical member with an adhesive layer.

The content of the polyrotaxane in the adhesive composition of the present invention is preferably from 0.01% by weight to 30% by weight, more preferably from 0.05% by weight to 25% by weight, even more preferably from 1% by weight to 20% by weight, based on the weight ratio. %, particularly preferably from 1% by weight to 15% by weight. By adjusting the content ratio of the polyrotaxane in the adhesive composition of the present invention to the above range, it is possible to provide adhesion which is more excellent in stress relaxation property and durability and which can exhibit a further sufficiently low haze value. The adhesive composition of the agent layer, and an adhesive layer comprising the adhesive composition, an adhesive sheet comprising the adhesive layer, and an optical member with an adhesive layer can be provided.

<(Meth)acrylic polymer>

The (meth)acrylic polymer includes a structural unit derived from a monomer having no aromatic ring structure, and a structural unit derived from a monomer having an aromatic ring structure. The (meth)acrylic polymer is preferably composed of a structural unit derived from a monomer having no aromatic ring structure and a structural unit derived from a monomer having an aromatic ring structure. By providing a (meth)acrylic polymer comprising a structural unit derived from a monomer having no aromatic ring structure and a structural unit derived from a monomer having an aromatic ring structure, stress relaxation and durability can be provided. An adhesive composition which is excellent in an adhesive layer which exhibits a sufficiently low haze value, and which can provide an adhesive layer comprising such an adhesive composition, an adhesive sheet comprising the adhesive layer, and an adhesive The optical component of the layer.

The "structural unit derived from a monomer" is a repeating structural unit derived from a monomer of a polymerization reaction, for example, when the monomer is represented by "Ra(Rb)=Rc(Rd)", the structure derived from the monomer The unit is "-Ra(Rb)-Rc(Rd)-". Here, Ra, Rb, Rc, and Rd are any groups bonded to the unsaturated double bond of the monomer.

The content ratio of the structural unit derived from the monomer having an aromatic ring structure in the (meth)acrylic polymer is preferably from 1% by weight to 35% by weight, more preferably from 3% by weight to 30% by weight, based on the weight ratio. More preferably, it is 5% by weight to 28% by weight, particularly preferably 8% by weight to 25% by weight, most preferably 10% by weight to 23% by weight. By adjusting the content ratio of the structural unit derived from the monomer having an aromatic ring structure in the (meth)acrylic polymer to the above range, it is possible to provide excellent stress relaxation and durability and to exhibit further An adhesive composition of an adhesive layer of sufficiently low haze value, and an adhesive layer comprising the adhesive composition, an adhesive sheet comprising the adhesive layer, and an optical member with an adhesive layer.

Furthermore, in the present invention, the (meth)acrylic polymer is derived from an aromatic The content ratio of the structural unit of the monomer of the ring structure is treated as substantially the same as the content ratio of the monomer having an aromatic ring structure among all the monomer components for producing the (meth)acrylic polymer.

The content ratio of the structural unit derived from the monomer having no aromatic ring structure in the (meth)acrylic polymer is preferably from 65% by weight to 99% by weight, more preferably from 70% by weight to 97% by weight, based on the weight ratio. More preferably, it is 72% by weight to 95% by weight, particularly preferably 75% by weight to 92% by weight, most preferably 77% by weight to 90% by weight. By adjusting the content ratio of the structural unit derived from the monomer having no aromatic ring structure in the (meth)acrylic polymer to the above range, it is possible to provide excellent stress relaxation property and durability and can be expressed. An adhesive composition of an adhesive layer further having a sufficiently low haze value, and an adhesive layer comprising the adhesive composition, an adhesive sheet comprising the adhesive layer, and an optical member with an adhesive layer .

Further, in the present invention, the content ratio of the structural unit derived from the monomer having no aromatic ring structure in the (meth)acrylic polymer is substantially the same as that used for the production of the (meth)acrylic polymer. The content ratio of the monomer having no aromatic ring structure among all the monomer components is the same.

The monomer having no aromatic ring structure may be any suitable monomer within a range that does not impair the effects of the present invention as long as it is a polymerizable monomer having an unsaturated double bond and does not have an aromatic ring structure. . The aromatic ring structure may be a single ring structure or a complex ring (condensed ring) structure.

The monomer having no aromatic ring structure, for example, one or more polymerizable functional groups having an unsaturated double bond such as a (meth) acrylonitrile group or a vinyl group, for the purpose of improving adhesion or heat resistance Comonomer.

Specific examples of such a comonomer include 2-hydroxyethyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, and (methyl). ) 6-hydroxyhexyl acrylate, 8-hydroxyoctyl (meth)acrylate, 10-hydroxyindole (meth)acrylate a monomer having a hydroxyl group such as ester, 12-hydroxylauryl (meth)acrylate, (4-hydroxymethylcyclohexyl)methyl acrylate; (meth)acrylic acid, carboxyethyl (meth)acrylate, (methyl) a carboxyl group-containing monomer such as carboxypentyl acrylate, itaconic acid, maleic acid, fumaric acid or crotonic acid; an acid anhydride group-containing monomer such as maleic anhydride or itaconic acid; and a caprolactone adduct of acrylic acid. ; styrene sulfonic acid, allyl sulfonic acid, 2-(methyl) propylene decylamine-2-methylpropane sulfonic acid, (meth) acrylamide propylene sulfonic acid, sulfopropyl (meth) acrylate, a monomer containing a sulfonic acid group such as (meth)acryloxynaphthalenesulfonic acid or a monomer having a phosphate group such as 2-hydroxyethyl acryloylphosphoryl phosphate.

Moreover, as such a comonomer, the modified monomer for the purpose of modification is mentioned. Examples of such a modified monomer include (meth)acrylamide, N,N-dimethyl(meth)acrylamide, N-butyl(meth)acrylamide, and N-hydroxyl. (N-substituted) guanamine monomer such as methyl (meth) acrylamide or N-methylolpropane (meth) acrylamide; aminoethyl (meth) acrylate, (meth) acrylate N,N-dimethylaminoethyl ester, alkylaminoalkyl (meth)acrylate such as tert-butylaminoethyl (meth)acrylate; methoxy (meth)acrylate (meth)acrylic acid alkoxyalkyl ester monomer such as ester, ethoxyethyl (meth)acrylate; N-(methyl) propylene oxymethylene succinimide, N-(A) Acetyl fluorenyl-6-oxyhexamethylene succinimide, N-(methyl) propylene decyl-8-oxy octamethyl succinimide, N-propylene fluorenyl Amber quinone imine monomer such as porphyrin; N-cyclohexylmaleimide, N-isopropylmaleimide, N-lauryl maleimide, N-phenylmaleimide And other maleic imine monomers; N-methyl Ikonium imine, N-ethyl Ikonium imine, N-butyl Ikonide, N-octylkonkine, An Ikonideimine monomer such as N-2-ethylhexyliconazole, N-cyclohexylkkonium imine or N-lauryl Ikonide.

Further, examples of such a modified monomer include vinyl acetate, vinyl propionate, N-vinyl pyrrolidone, methyl vinyl pyrrolidone, vinyl pyridine, and vinyl piperidone. Vinylpyrimidine Vinylpyr , vinyl pyrrole, vinyl imidazole, vinyl Azole, vinyl a vinyl monomer such as a porphyrin, an N-vinyl carboxamide, a styrene, an α-methylstyrene or an N-vinyl caprolactam; a cyanoacrylate monomer such as acrylonitrile or methacrylonitrile; An epoxy group-containing acrylic monomer such as glycidyl (meth)acrylate; polyethylene glycol (meth) acrylate, polypropylene glycol (meth) acrylate, methoxyethylene glycol (meth) acrylate a glycol-based acrylate monomer such as an ester or a methoxypolypropylene glycol (meth) acrylate; a tetrahydrofurfuryl (meth) acrylate, a fluorine (meth) acrylate, or a poly methoxy (meth) acrylate; An acrylate monomer such as 2-methoxyethyl acrylate. Further, examples of such a modified monomer include isoprene, butadiene, isobutylene, and vinyl ether.

Further, examples of the comonomer include a decane-based monomer containing a ruthenium atom. Examples of such a decane-based monomer include 3-propenyloxypropyltriethoxydecane, vinyltrimethoxydecane, vinyltriethoxydecane, and 4-vinylbutyltrimethoxy. Decane, 4-vinylbutyltriethoxydecane, 8-vinyloctyltrimethoxydecane, 8-vinyloctyltriethoxydecane, 10-methylpropenyloxydecyltrimethoxy Decane, 10-propenyloxydecyltrimethoxydecane, 10-methylpropenyloxydecyltriethoxydecane, 10-propenyloxydecyltriethoxydecane, and the like.

Further, examples of the comonomer include tripropylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, and bisphenol. A diglycidyl ether di(meth) acrylate, neopentyl glycol di (meth) acrylate, trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra ( (meth)acrylic acid and polyhydric alcohol, such as methyl acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, caprolactone modified dipentaerythritol hexa (meth) acrylate a polyfunctional monomer having two or more unsaturated double bonds such as a (meth) acryl fluorenyl group or a vinyl group; and an addition to the polyester skeleton, the epoxy skeleton, and the urethane skeleton; Polyester (meth) acrylate, epoxy (meth) acrylate, (meth) acrylate, etc. of unsaturated double bonds such as (meth) acrylonitrile or vinyl

As the monomer having no aromatic ring structure, it is preferred to contain (meth) acrylate, A (meth)acrylic monomer such as (meth)acrylic acid or a salt thereof (such as a sodium salt or a potassium salt) is used as a main monomer. The content ratio of the (meth)acrylic monomer in the monomer having no aromatic ring structure is preferably 50% by weight or more, more preferably 70% by weight to 100% by weight, still more preferably 90% by weight to 100% by weight. % by weight, particularly preferably from 95% by weight to 100% by weight. By adjusting the content ratio of the (meth)acrylic monomer in the monomer having no aromatic ring structure within the above range, it is possible to provide a mist which is excellent in stress relaxation property and durability and which can exhibit further sufficiently low fog. An adhesive composition of an adhesive layer of a degree, and an adhesive layer comprising the adhesive composition, an adhesive sheet comprising the adhesive layer, and an optical member with an adhesive layer.

The (meth)acrylic monomer is preferably a (meth) acrylate, (meth) acrylate or a salt thereof (such as a sodium salt or a potassium salt).

Examples of the (meth) acrylate include an alkyl (meth)acrylate having a carbon number of 1 to 30 (including a cycloalkyl group), a (meth)acrylate containing a hydroxyl group, and the like. The (meth) acrylate may be used alone or in combination of two or more.

Examples of the (meth)acrylic acid alkyl ester having an alkyl group having 1 to 30 carbon atoms (including a cycloalkyl group) include methyl (meth)acrylate, ethyl (meth)acrylate, and (methyl). ) propyl acrylate, isopropyl (meth) acrylate, butyl (meth) acrylate, isobutyl (meth) acrylate, second butyl (meth) acrylate, tert-butyl (meth) acrylate , pentyl (meth)acrylate, amyl(meth)acrylate, hexyl (meth)acrylate, cyclohexyl (meth)acrylate, (a) Heptyl acrylate, 2-ethylhexyl (meth) acrylate, octyl (meth) acrylate, isooctyl (meth) acrylate, decyl (meth) acrylate, isophthalic acid (meth) acrylate Ester, decyl (meth) acrylate, isodecyl (meth) acrylate, undecyl (meth) acrylate, dodecyl (meth) acrylate, tridecyl (meth) acrylate Ester, tetradecyl (meth) acrylate, pentadecyl (meth) acrylate, octadecyl (meth) acrylate, hexadecyl (meth) acrylate, (methyl) Epoxyalkyl acrylate, (meth)acrylic acid Ester An alkyl (meth)acrylate having an alkyl group having 1 to 30 carbon atoms (including a cycloalkyl group). Among the (meth) acrylates, an alkyl (meth) acrylate having an alkyl group having 2 to 20 carbon atoms (including a cycloalkyl group) is preferred, and an alkane having a carbon number of 4 to 18 is more preferred. An alkyl (meth)acrylate of a base (also containing a cycloalkyl group).

Examples of the hydroxyl group-containing (meth) acrylate include 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, and 4-hydroxybutyl (meth)acrylate.

The monomer having no aromatic ring structure is preferably an alkyl (meth)acrylate containing an alkyl group having 1 to 30 carbon atoms (including a cycloalkyl group). In this case, the content ratio of the alkyl (meth)acrylate having an alkyl group having 1 to 30 carbon atoms (including a cycloalkyl group) in the monomer having no aromatic ring structure is preferably a weight ratio. 50% by weight to 99.999% by weight, more preferably 70% by weight to 99.99% by weight, still more preferably 80% by weight to 99.9% by weight, particularly preferably 90% by weight to 99.5% by weight, most preferably 95% by weight to 99.5% by weight weight%. By adjusting the content ratio of the alkyl (meth) acrylate having an alkyl group having 1 to 30 carbon atoms (including a cycloalkyl group) in the monomer having no aromatic ring structure to the above range, it is possible to provide An adhesive composition constituting an adhesive layer excellent in stress relaxation property and durability and capable of exhibiting a further sufficiently low haze value, and an adhesive layer containing the adhesive composition, comprising the adhesive layer Adhesive sheet and optical member with adhesive layer.

The monomer having no aromatic ring structure preferably contains a hydroxyl group-containing (meth) acrylate. In this case, the content ratio of the hydroxyl group-containing (meth) acrylate in the monomer having no aromatic ring structure is preferably from 0.001% by weight to 50% by weight, more preferably from 0.01% by weight to 30% by weight. The weight %, more preferably 0.1% by weight to 20% by weight, particularly preferably 0.5% by weight to 10% by weight, most preferably 0.5% by weight to 5% by weight. By adjusting the content ratio of the hydroxyl group-containing (meth) acrylate in the monomer having no aromatic ring structure to the above range, it is possible to provide excellent stress relaxation property and durability, and to exhibit further sufficiently low. An adhesive composition of an adhesive layer of haze value, and an adhesive layer comprising the adhesive composition, an adhesive sheet comprising the adhesive layer, and an adhesive attached thereto The optical component of the layer.

The monomer having no aromatic ring structure preferably contains (meth)acrylic acid or a salt thereof (sodium salt or potassium salt, etc.). In this case, the content ratio of (meth)acrylic acid or a salt thereof (sodium salt or potassium salt) in the monomer having no aromatic ring structure is preferably from 0% by weight to 50% by weight based on the weight ratio, more preferably It is preferably from 0.01% by weight to 40% by weight, more preferably from 0.1% by weight to 30% by weight, even more preferably from 0.5% by weight to 20% by weight, most preferably from 1% by weight to 10% by weight. By adjusting the content ratio of (meth)acrylic acid or a salt thereof (sodium salt or potassium salt) in the monomer having no aromatic ring structure to the above range, it is possible to provide excellent stress relaxation property and durability. An adhesive composition which exhibits a further sufficiently low haze value of an adhesive layer, and which can provide an adhesive layer comprising the adhesive composition, an adhesive sheet comprising the adhesive layer, and an adhesive layer Optical member.

When the monomer having an aromatic ring structure is a polymerizable monomer having an unsaturated double bond and has an aromatic ring structure, any suitable monomer can be used without departing from the effects of the present invention. The aromatic ring structure may be a single ring structure or a complex ring (condensed ring) structure.

Examples of the monomer having an aromatic ring structure include benzyl acrylate, phenoxyethyl acrylate, phenyl acrylate, phenoxy (meth) acrylate, and phenoxyethyl (meth) acrylate. Benzyl (meth) acrylate, phenoxy diethylene glycol (meth) acrylate, ethylene oxide modified nonyl phenol (meth) acrylate, hydroxyethylated β-naphthol acrylate, ( Biphenyl (meth) acrylate and the like. Further, for example, phenol ethylene oxide modified (meth) acrylate, (meth) acrylate 2-naphthyl ethyl acrylate, 2-naphthyloxyethyl acrylate, (meth) acrylate 2-(4- Methoxy-1-naphthyloxy)ethyl ester, phenoxypropyl (meth)acrylate, phenoxy diethylene glycol (meth) acrylate, thiol acrylate, pyridyl acrylate, pyrrolyl acrylate , phenyl acrylate, poly(meth) acrylate styrene and the like. The monomer having an aromatic ring structure may be one type or two or more types.

The monomer having an aromatic ring structure preferably comprises a benzyl acrylate and acrylic acid. At least one of phenoxyethyl esters. When the monomer having an aromatic ring structure contains at least one selected from the group consisting of benzyl acrylate and phenoxyethyl acrylate, it is possible to provide a haze value which is excellent in stress relaxation property and durability and which can exhibit a sufficiently sufficiently low haze value. The adhesive composition of the adhesive layer, and an adhesive layer comprising the adhesive composition, an adhesive sheet comprising the adhesive layer, and an optical member with an adhesive layer.

The (meth)acrylic polymer can be produced by any suitable method. As a method for producing the (meth)acrylic polymer, for example, a known production method such as solution polymerization, bulk polymerization, emulsion polymerization, or various radical polymerization can be suitably selected. Further, the obtained (meth)acrylic polymer may be any of a random copolymer, a block copolymer, and a graft copolymer. Further, in the solution polymerization, as the polymerization solvent, for example, ethyl acetate, toluene or the like can be used. As a specific example of the solution polymerization, for example, a polymerization initiator is added under an inert gas flow such as nitrogen, and solution polymerization is usually carried out under the reaction conditions of about 50 to 70 ° C for about 5 to 30 hours.

The polymerization initiator, the chain transfer agent, the emulsifier, and the like used in the radical polymerization can be appropriately selected as appropriate within the range not impairing the effects of the present invention. Further, the weight average molecular weight of the (meth)acrylic polymer (A) can be controlled by, for example, the amount of the polymerization initiator used, the amount of the chain transfer agent used, the reaction conditions, and the like, and is suitable according to the types thereof. Adjust the usage of these, etc.

Examples of the polymerization initiator include 2,2'-azobisisobutyronitrile, 2,2'-azobis(2-amidinopropane) dihydrochloride, and 2,2'-azodiene. [2-(5-Methyl-2-imidazolin-2-yl)propane] dihydrochloride, 2,2'-azobis(2-methylpropionamidine) disulfate, 2,2'- Azobis(N,N'-dimethyleneisobutylphosphonium), 2,2'-azobis[N-(2-carboxyethyl)-2-methylpropionamidine] hydrate (and pure light) Manufactured by a pharmaceutical company, VA-057), such as azo initiators, persulfate such as potassium persulfate or ammonium persulfate, di(2-ethylhexyl) peroxydicarbonate, and di(2-dicarbonate) Tertiary butylcyclohexyl) ester, dibutyl phthalate dihydrate, tert-butyl peroxy neodecanoate, third hexyl peroxypivalate, tert-butyl peroxypivalate Oxidized dilaurin Di-n-octyl oxidized, 1,2-,3,3-tetramethylbutyl peroxy (2-ethylhexanoic acid), bis(4-methylbenzhydryl) peroxide, dibenzoguanidine peroxide , peroxide-based isomerization of isobutyl isobutyrate, 1,1-di(t-hexylperoxy)cyclohexane, tert-butyl hydroperoxide, hydrogen peroxide, etc., persulfuric acid A combination of a salt and a sodium hydrogen sulfite, a combination of a peroxide and sodium ascorbate, and the like, and a redox initiator, which is a combination of a peroxide and a reducing agent, is not limited thereto.

The polymerization initiator may be used singly or in combination of two or more.

The amount of the polymerization initiator to be used is preferably from 0.005 part by weight to 1 part by weight, more preferably 0.02 part by weight, per 100 parts by weight of all the monomer components for producing the (meth)acrylic polymer. 0.5 parts by weight.

Further, when a (meth)acrylic polymer is produced by using, for example, 2,2'-azobisisobutyronitrile as a polymerization initiator, the amount of the polymerization initiator used is relative to that used for the production (methyl). The 100 parts by weight of all the monomer components of the acrylic polymer is preferably 0.06 part by weight to 0.2 part by weight, more preferably 0.08 part by weight to 0.175 part by weight.

Examples of the chain transfer agent include lauryl mercaptan, glycidyl mercaptan, mercaptoacetic acid, 2-mercaptoethanol, thioglycolic acid, 2-ethylhexyl thioglycolate, and 2,3-didecyl. -1-propanol and the like. The chain transfer agent may be used singly or in combination of two or more.

The amount of the chain transfer agent used is preferably 0.1 part by weight or less based on 100 parts by weight of all the monomer components for producing the (meth)acrylic polymer.

Examples of the emulsifier used in the case of performing emulsion polymerization include sodium lauryl sulfate, ammonium lauryl sulfate, sodium dodecylbenzenesulfonate, polyoxyethylene alkyl ether sulfate, and polyoxyethylene alkyl. Anionic emulsifier such as sodium phenyl ether sulfate; nonionic emulsifier such as polyoxyethylene alkyl ether, polyoxyethylene alkyl phenyl ether, polyoxyethylene fatty acid ester, polyoxyethylene-polyoxypropylene block polymer, etc. . These emulsifiers may be used singly or in combination of two or more.

Further, as the emulsifier, it is also possible to use a propylene group or an allyl ether group to introduce a free A reactive emulsifier based on a polymerizable functional group. As such a reactive emulsifier, for example, AQUALON HS-10, HS-20, KH-10, BC-05, BC-10, BC-20 (all of which are manufactured by First Industrial Pharmaceutical Co., Ltd.), and ADEKA REASOAP are present. SE10N (made by Asahi Chemical Co., Ltd.). Since the reactive emulsifier is introduced into the polymer chain after polymerization, the water resistance becomes good and is preferable.

The amount of the emulsifier used is preferably 0.3 parts by weight to 5 parts from the viewpoint of polymerization stability or mechanical stability with respect to 100 parts by weight of all the monomer components used for the production of the (meth)acrylic polymer. The parts by weight are more preferably 0.5 parts by weight to 1 part by weight.

The (meth)acrylic polymer of the present invention which can be obtained by the above-described method generally has a weight average molecular weight of from 500,000 to 3,000,000. The weight average molecular weight of the (meth)acrylic polymer in the present invention is preferably from 700,000 to 2.7 million, more preferably from 800,000 to 2.5 million, in view of durability, particularly heat resistance. When the weight average molecular weight of the (meth)acrylic polymer in the present invention is less than 500,000, it is not preferable in terms of heat resistance. In addition, when the weight average molecular weight of the (meth)acrylic polymer in the present invention is more than 3,000,000, it is not preferable because a large amount of a diluent solvent is required to adjust the viscosity for coating, and the cost is increased. In addition, the weight average molecular weight is a value calculated by GPC (gel permeation chromatography) and calculated by polystyrene conversion.

<polyrotaxane>

The polyrotaxane has a cyclic molecule, a linear molecule that penetrates the opening of the cyclic molecule, and is disposed at both ends of the linear molecule so that the cyclic molecule does not detach from the linear molecule. Blocking base.

The cyclic molecule is a molecule that can move on a linear molecule in a linear form in the opening, and has a hydroxyl group or an active energy ray polymerizable group, so as not to damage the ring-shaped molecule. Any suitable cyclic molecule is employed within the scope of the effects of the present invention. In the present specification, the "ring" of the "cyclic molecule" means substantially "cyclic". That is, as long as it can move on the linear molecule, the cyclic molecule may also be incompletely closed loop.

Specific examples of the cyclic molecule include a cyclic polymer such as a cyclic polyether, a cyclic polyester, a cyclic polyether amine, and a cyclic polyamine, and an α-cyclodextrin and a β-ring. Cyclodextrin such as dextrin and γ-cyclodextrin. Among them, cyclodextrin such as α-cyclodextrin, β-cyclodextrin, and γ-cyclodextrin is preferred from the viewpoint of relatively easy availability and selection of a plurality of types of blocking groups. The cyclic molecule may be mixed in two or more kinds in the polyrotaxane.

In the polyrotaxane, the above cyclic molecule preferably has a hydroxyl group. Further, a part of such a hydroxyl group may be substituted with another group. Examples of such other groups include a hydrophilic group, a hydrophobic group, and a photoreactive group.

The linear molecule is not particularly limited as long as it is a molecule or a substance which is integrated by mechanical bonding without being bonded by a chemical bond such as a covalent bond, and is linear. In addition, in the present specification, the "straight chain" of "linear molecule" means substantially "straight chain". That is, the linear molecule may have a branch as long as the cyclic molecule can move on the linear molecule.

As the linear molecule, for example, polyethylene glycol, polypropylene glycol, polyisoprene, polyisobutylene, polybutadiene, polytetrahydrofuran, polyacrylate, polydimethyl siloxane, polyethylene, or the like is preferable. Polypropylene, etc. The linear molecules may be one type or two or more types.

The number average molecular weight of the linear molecules is preferably from 1,000 to 300,000, more preferably from 2,000 to 200,000, and even more preferably from 4,000 to 100,000.

The blocking group may be any suitable group within a range that does not impair the effects of the present invention as long as it can maintain a matrix in which the cyclic molecules are in a string shape. Examples of such a group include dinitrophenyls, cyclodextrins, adamantyls, trityls, fluoresceins, anthraquinones, anthracenes, and a number average molecular weight of 1,000 to 1,000,000. The main chain or side chain of the polymer. The blocking group may be one type or two or more types.

In polyrotaxane, the largest molecular group is bound by a linear molecule into a string. When the amount of the cyclic molecule (maximum inclusion amount) is limited to 100%, the cyclic molecule is preferably 0.1% to 60%, more preferably 1% to 50%, and still more preferably 5 The amount of %~40% is bundled in a linear molecule. Furthermore, the maximum amount of inclusion of the cyclic molecule can be determined by the length of the linear molecule and the thickness of the cyclic molecule. For example, when the linear molecule is polyethylene glycol and the cyclic molecule is an α-cyclodextrin molecule, the maximum amount of inclusion is experimentally determined (refer to Macromolecules 1993, 26, 5698-5703).

As the polyrotaxane, for example, polyrotaxane described in JP-A-2005-154675, JP-A-2009-270119, WO2009/145073, and the like can be used.

The polyrotaxane can be obtained, for example, by the method described in JP-A-2005-154675, JP-A-2009-270119, WO2009/145073, and the like. Further, a commercially available product (for example, "SeRM (registered trademark) super polymer" series manufactured by Advanced Soft Materials Co., Ltd.) can also be used.

<crosslinker>

The adhesive composition of the present invention may also contain a crosslinking agent. Examples of such a crosslinking agent include an organic crosslinking agent or a polyfunctional metal chelate compound.

Examples of the organic crosslinking agent include an isocyanate crosslinking agent, a peroxide crosslinking agent, an epoxy crosslinking agent, and an imide crosslinking agent. The polyfunctional metal chelate is a covalent bond or a coordination bond of an organic compound with a polyvalent metal atom. Examples of the polyvalent metal atom include Al, Cr, Zr, Co, Cu, Fe, Ni, V, Zn, In, Ca, Mg, Mn, Y, Ce, Sr, Ba, Mo, La, and Sn. Ti et al. Examples of the atom in the organic compound which is a covalent bond or a coordinate bond include an oxygen atom, and examples of the organic compound include an alkyl ester, an alcohol compound, a carboxylic acid compound, an ether compound, and a ketone compound.

As the crosslinking agent, an isocyanate crosslinking agent is preferred. Examples of the isocyanate crosslinking agent include toluene diisocyanate, chlorophenyl diisocyanate, and tetramethylene diiso. Cyanate ester, benzodimethyl diisocyanate, hydrogenated benzodimethyl diisocyanate, diphenylmethane diisocyanate, hydrogenated diphenylmethane diisocyanate, hexamethylene diisocyanate, isophorone II a diisocyanate such as an isocyanate; a polyisocyanate compound derived from such a diisocyanate; an adduct obtained by adding such a diisocyanate to trimethylolpropane or the like; and isocyanide as a terpolymer of the diisocyanate a urate body; a biuret body as a reactant of hexamethylene diisocyanate and water or a tertiary alcohol; and the diisocyanate and polyether polyol, polyester polyol, acrylic polyol, polybutylene A urethane prepolymer type isocyanate obtained by an addition reaction such as an olefin polyol or a polyisoprene polyol.

Preferred examples of the isocyanate crosslinking agent include toluene diisocyanate, chlorophenyl diisocyanate, tetramethylene diisocyanate, benzodimethyl diisocyanate, hydrogenated benzodimethyl diisocyanate, and diphenylmethane II. A diisocyanate such as an isocyanate, hydrogenated diphenylmethane diisocyanate, hexamethylene diisocyanate or isophorone diisocyanate; or a polyisocyanate compound derived from such a diisocyanate.

The diisocyanate is more preferably hexamethylene diisocyanate, hydrogenated dimethyl diisocyanate or isophorone diisocyanate.

The polyisocyanate compound derived from a diisocyanate is more preferably a polyol-modified hexamethylene diisocyanate, a polyol-modified hydrogenated dimethyl dimethyl diisocyanate, a terpolymer-type hydrogenated dimethyl dimethyl diisocyanate, or a polyhydric alcohol. Modified isophorone diisocyanate.

The isocyanate-based crosslinking agent rapidly reacts with a hydroxyl group by causing an acid or a base contained in a polymer to act as a catalyst, so that it is advantageous in terms of speeding up crosslinking. It is a polyisocyanate compound derived from a diisocyanate.

In the case of using a crosslinking agent, the amount thereof is preferably 0.001% by weight to 10% by weight, more preferably 0.01% by weight to 5% by weight based on the (meth)acrylic polymer. More preferably, it is 0.03 wt% to 3% by weight, particularly preferably 0.03 wt% to 2 wt%, most preferably 0.05 wt% to 1.5 wt%. By adjusting the ratio of use of the crosslinking agent In the above range, an appropriate crosslinking reaction can be produced, and an adhesive composition which is excellent in stress relaxation property and durability and which can exhibit a further sufficiently low haze value can be provided, and can be provided. An adhesive layer comprising such an adhesive composition, an adhesive sheet comprising such an adhesive layer, and an optical member with an adhesive layer.

<Other ingredients>

The adhesive composition of the present invention may also contain other ingredients. The adhesive composition of the present invention may contain any appropriate additives within the range not impairing the effects of the present invention. Examples of such an additive include powders such as coloring agents and pigments, dyes, surfactants, plasticizers, adhesion-imparting agents, surface lubricants, leveling agents, softeners, antioxidants, and anti-aging agents. Antistatic agent, light stabilizer, ultraviolet absorber, polymerization inhibitor, inorganic or organic filler, metal powder, particulate, foil, and the like. Further, a reducing agent may be added as an additive to the redox system without impairing the effects of the present invention.

A decane coupling agent may be contained in the adhesive composition of the present invention. The durability of the adhesive composition of the present invention can be improved by containing a decane coupling agent.

Specific examples of the decane coupling agent include 3-glycidoxypropyltrimethoxydecane, 3-glycidoxypropyltriethoxydecane, and 3-glycidoxypropylmethyldiene. An epoxy group-containing decane coupling agent such as ethoxy decane or 2-(3,4-epoxycyclohexyl)ethyltrimethoxy decane; 3-aminopropyltrimethoxydecane, N-2-( Aminoethyl)-3-aminopropylmethyldimethoxydecane, 3-triethoxydecyl-N-(1,3-dimethylbutylidene)propylamine, N-phenyl - an amide-containing coupling agent such as γ-aminopropyltrimethoxydecane; 3-propenyloxypropyltrimethoxydecane, 3-methylpropenyloxypropyltriethoxydecane, etc. a (meth)acrylic decane coupling agent; an isocyanate group-containing decane coupling agent such as 3-isocyanate propyl triethoxy decane.

The decane coupling agent may have a general formula: -SiR _a M _3-a (wherein R may also have a substituent of a monovalent organic group having 1 to 20 carbon atoms, a M-based hydroxyl group or a hydrolyzable group, a is an integer from 0 to 2. Wherein, when there are a plurality of R, the plurality of Rs may be the same or different, and when there are a plurality of M, the plurality of M may be the same or different) the represented reactive decane Base and acetaminophen. As a commercial item of the decane coupling agent which has a reactive decyl group and an ethyl hydrazine group as mentioned above, A100 etc. by the Research Chemicals company are mentioned, for example.

The decane coupling agent may be used alone or in combination of two or more.

The content of the decane coupling agent is preferably 0.001 part by weight to 5 parts by weight, more preferably 0.01 part by weight to 1 part by weight, even more preferably 0.02, based on 100 parts by weight of the (meth)acrylic polymer. It is preferably from 0.05 part by weight to 0.6 parts by weight, based on parts by weight to 1 part by weight. By adjusting the content of the decane coupling agent to the above range, the durability of the adhesive composition of the present invention can be improved, and the adhesion to an optical member such as a liquid crystal cell can be appropriately maintained.

However, the adhesive composition of the present invention can provide an adhesive composition which is excellent in stress relaxation property and durability and which can exhibit a low haze value even if it does not contain other components, and can provide inclusion. An adhesive layer of such an adhesive composition, an adhesive sheet comprising the adhesive layer, and an optical member with an adhesive layer. Therefore, in order to suppress the decrease or exudation of the gel fraction, it is preferred to contain other components as needed.

The adhesive composition of the present invention can form an adhesive layer. When the adhesive layer is formed, it is preferred to adjust the addition amount of the crosslinking agent as a whole, and to fully consider the crosslinking treatment temperature or crosslinking when performing the crosslinking treatment. The impact of processing time.

The crosslinking treatment temperature or the crosslinking treatment time can be adjusted depending on the crosslinking agent used. The crosslinking treatment temperature is preferably 170 ° C or lower.

The crosslinking treatment may be carried out at a temperature at the drying step of the adhesive layer, or may be carried out separately after the drying step by providing a crosslinking treatment step for crosslinking treatment.

Regarding the crosslinking treatment time, it can be set in consideration of productivity or workability. The crosslinking treatment time is preferably from 0.2 minutes to 20 minutes, more preferably from 0.5 minutes to 10 minutes.

As an example of the adhesive layer, in the case of the adhesive layer in the polarizing film to which the adhesive layer is attached, the adhesive composition of the present invention forms an adhesive layer on at least one side of the polarizing film.

For example, the adhesive composition of the present invention is applied to a release-treated separator or the like, and a polymerization solvent or the like is dried to form an adhesive layer, and then transferred to a polarizing film. A method of applying the adhesive composition of the present invention to a polarizing film, drying a polymerization solvent or the like, and forming an adhesive layer on a polarizing film. Further, when the adhesive composition of the present invention is applied, one or more solvents other than the polymerization solvent may be appropriately added.

<Method for Producing Adhesive Composition>

The adhesive composition of the present invention can be produced by any appropriate method within the range not impairing the effects of the present invention. For example, the (meth)acrylic polymer, the polyrotaxane, and other components as needed may be added to a stirrer or the like together with any appropriate solvent, stirred and mixed, and optionally A method of adding a crosslinking agent and stirring.

≪Adhesive layer≫

The adhesive layer of the present invention comprises the adhesive composition of the present invention.

The adhesive layer of the present invention is preferably formed by hardening the adhesive composition of the present invention.

The adhesive layer of the present invention is preferably formed by applying the adhesive composition of the present invention to any suitable substrate and hardening it.

As a method of hardening, any appropriate method can be employed. For example, heat hardening and light hardening.

As the thickness of the adhesive layer of the present invention, any appropriate thickness can be employed depending on the purpose. The thickness of the adhesive layer is preferably from 0.1 μm to 100 μm, more preferably from 2 μm to 50 μm, still more preferably from 2 μm to 40 μm, particularly preferably from 5 μm to 35 μm.

The haze value of the adhesive layer of the present invention is preferably less than 1.0, more preferably 0.95 or less, still more preferably 0.90 or less, still more preferably 0.85 or less, still more preferably 0.80 or less, and particularly preferably 0.75 or less. The best is below 0.70.

≪Adhesive sheet ≫

The adhesive sheet of the present invention comprises the adhesive layer and the substrate layer of the present invention. The adhesive sheet of the present invention may contain any suitable other layer within the range not impairing the effects of the present invention. The adhesive sheet of the present invention is preferably a laminate of the adhesive layer and the substrate layer of the present invention.

As the thickness of the adhesive sheet of the present invention, any appropriate thickness can be employed depending on the purpose. The thickness of the adhesive sheet is preferably 10 μm to 1000 μm, more preferably 10 μm to 500 μm, still more preferably 20 μm to 500 μm, and particularly preferably 30 μm to 400 μm.

The base material layer may be a single layer or a laminate of two or more layers. The substrate layer can also be an extender.

As the base material layer, any appropriate base material layer can be employed within a range that does not impair the effects of the present invention. Examples of the material of the base material layer include plastic, paper, metal film, and nonwoven fabric. It is preferably plastic. The base material layer may contain one type of material, or may contain two or more types of materials. For example, it is also possible to include two or more kinds of plastics.

Examples of the plastic material include a polyester resin, a polyamide resin, and a polyolefin resin. Examples of the polyester resin include polyethylene terephthalate, polybutylene terephthalate, and polyethylene naphthalate. Examples of the polyolefin-based resin include a homopolymer of an olefin monomer, a copolymer of an olefin monomer, and the like. Specific examples of the polyolefin-based resin include homopolypropylene; a propylene-based copolymer such as a block system, a random system, or a graft system in which an ethylene component is used as a copolymer component; and a reactor TPO; low density and high density; Ethylene polymer with density, linear low density, ultra low density, etc.; ethylene-propylene copolymer, ethylene-vinyl acetate copolymer, ethylene-methyl acrylate copolymer, ethylene-ethyl acrylate copolymer, ethylene-acrylic acid butyl An ethylene copolymer such as an ester copolymer, an ethylene-methacrylic acid copolymer or an ethylene-methyl methacrylate copolymer.

The substrate layer may optionally contain any suitable additives. Examples of the additive which may be contained in the base layer include an antioxidant, an ultraviolet absorber, a light stabilizer, an antistatic agent, a filler, a pigment, and the like. The kind, number, and amount of the additives which can be contained in the base material layer can be appropriately set depending on the purpose. In particular, when the material of the base material layer is a plastic, it is preferable to contain several kinds of the above additives for the purpose of preventing deterioration or the like. From the viewpoints of improvement in weather resistance, etc., as an additive, an antioxidant, a UV absorber, a light stabilizer, and a filler are especially preferable.

The adhesive sheet of the present invention may also have a release liner on the surface of the adhesive layer.

As the release liner, any suitable separator can be employed. As such a release liner, for example, a substrate having a release layer such as a plastic film or paper surface-treated with a release agent such as a polyfluorene-based, long-chain alkyl-based, fluorine-based or molybdenum sulfide; Low adhesion of fluorine-based polymers such as polytetrafluoroethylene, polychlorotrifluoroethylene, polyvinyl fluoride, polyvinylidene fluoride, tetrafluoroethylene-hexafluoropropylene copolymer, and chlorofluoroethylene-vinylidene fluoride copolymer A base material; a low-adhesive base material containing a nonpolar polymer such as an olefin resin (for example, polyethylene or polypropylene).

The adhesive sheet of the present invention can be produced by any suitable method. As such a production method, for example, a method in which the pressure-sensitive adhesive composition of the present invention is applied to a release liner or the like, and a polymerization solvent or the like is dried and removed is exemplified. At the time of coating the adhesive composition of the present invention, it is also possible to appropriately re-add one or more solvents other than the polymerization solvent. In such a step, as a method of drying the adhesive composition of the present invention, any appropriate method can be employed depending on the purpose. As such a method, a method of heating and drying the coating film obtained by applying the pressure-sensitive adhesive composition of the present invention is preferred. The heating and drying temperature in this method is preferably from 40 ° C to 200 ° C, more preferably from 50 ° C to 180 ° C, and still more preferably from 70 ° C to 170 ° C. By adjusting the heating and drying temperature to the above range, an adhesive sheet having excellent adhesive properties can be obtained. As the heating and drying time, any appropriate time can be employed. The heating and drying time is preferably from 5 seconds to 20 minutes, more preferably from 5 seconds to 10 minutes, and further Good for 10 seconds to 5 minutes.

As a method of forming the adhesive layer, various methods can be used. Specific examples thereof include roll coating, contact roll coating, gravure coating, reverse coating, roll coating, spray coating, dip roller coating, bar coating, blade coating, and air knife coating. A cloth, a curtain coating, a lip coating, an extrusion coating method using a die coater or the like.

Optical member with adhesive layer≫

The optical member with an adhesive layer of the present invention comprises the adhesive layer of the present invention and an optical member. The optical member to which the adhesive layer of the present invention is applied may also include any suitable other layer within the range not impairing the effects of the present invention. The optical member with the adhesive layer of the present invention is preferably a laminate of the adhesive layer and the optical member of the present invention.

The thickness of the optical member to which the adhesive layer of the present invention is applied may be any appropriate thickness depending on the purpose. The thickness of the optical member to which the adhesive layer is attached is preferably 10 μm to 1000 μm, more preferably 30 μm to 750 μm, still more preferably 40 μm to 500 μm, and particularly preferably 50 μm to 400 μm.

The optical member may be a single layer or a laminate of two or more layers. The optical member can also be an extender.

Examples of the optical member include a polarizing plate, a retardation plate, an optical compensation plate, a brightness enhancement plate, a liquid crystal display device, an organic EL display device, and an image display device such as a PDP.

The optical member of the adhesive layer of the present invention may also comprise a release liner on the surface of the adhesive layer.

As the release liner, any suitable separator can be employed. As such a release liner, for example, a substrate having a release layer such as a plastic film or paper surface-treated with a release agent such as a polyfluorene-based, long-chain alkyl-based, fluorine-based or molybdenum sulfide; Low adhesion of fluorine-based polymers such as polytetrafluoroethylene, polychlorotrifluoroethylene, polyvinyl fluoride, polyvinylidene fluoride, tetrafluoroethylene-hexafluoropropylene copolymer, and chlorofluoroethylene-vinylidene fluoride copolymer base A low-adhesive substrate containing a nonpolar polymer such as an olefin resin (for example, polyethylene or polypropylene).

≪Image display device≫

The optical member to which the adhesive layer of the present invention is applied is preferably used in the formation of an image display device such as a liquid crystal display device, and as such a type, any appropriate one can be employed without damaging the effects of the present invention. kind. That is, the image display device of the present invention comprises at least one optical member of the present invention with an adhesive layer. As the optical member, a polarizing plate is preferred. The polarizing plate can be manufactured by any suitable method.

As the polarizing plate, it is generally used for a transparent protective film on one side or both sides of a polarizing element. As the polarizing element, any appropriate polarizing element can be employed without departing from the effects of the present invention. As such a polarizing element, for example, iodine or a two-color adsorption on a hydrophilic polymer film such as a polyvinyl alcohol film, a partially formalized polyvinyl alcohol film, or an ethylene-vinyl acetate copolymer partial saponified film is used. The dichroic substance of the dye is uniaxially stretched, and a polyene-based alignment film such as a dehydrated material of polyvinyl alcohol or a dehydrochlorination product of polyvinyl chloride is used. Among these, a polarizing element including a polyvinyl alcohol-based film and a dichroic substance such as iodine is preferable. As the thickness of the polarizing element, any appropriate thickness can be employed within a range that does not impair the effects of the present invention. As such a thickness, it is preferably 5 μm to 80 μm.

As the material constituting the transparent protective film, for example, a thermoplastic resin excellent in transparency, mechanical strength, thermal stability, moisture barrier property, and isotropic property can be used. Specific examples of such a thermoplastic resin include a cellulose resin such as triethyl fluorene cellulose, a polyester resin, a polyether oxime resin, a polyfluorene resin, a polycarbonate resin, a polyamide resin, and a polyimine. Resin, polyolefin resin, (meth)acrylic resin, cyclic polyolefin resin (for example, An olefin resin, a polyarylate resin, a polystyrene resin, a polyvinyl alcohol resin, a mixture thereof, and the like.

The content of the above thermoplastic resin in the transparent protective film is preferably from 50% by weight to 100% by weight. The amount % is more preferably from 50% by weight to 99% by weight, still more preferably from 60% by weight to 98% by weight, particularly preferably from 70% by weight to 97% by weight. When the content of the above thermoplastic resin in the transparent protective film is less than 50% by weight, the high transparency and the like which the thermoplastic resin originally has cannot be sufficiently exhibited.

The transparent protective film is bonded to the one or both sides of the polarizing element by an adhesive layer. A thermosetting resin such as a (meth)acrylic resin, a urethane-based resin, an urethane-based resin, an epoxy resin, or a polyfluorene-based resin may be used for at least one surface of the polarizing element or The ultraviolet curable resin is used as a transparent protective film. One or more optional additives may be contained in the transparent protective film. Examples of the additive include a UV absorber, an antioxidant, a lubricant, a plasticizer, a release agent, a coloring inhibitor, a flame retardant, a nucleating agent, an antistatic agent, a pigment, a colorant, and the like.

An adhesive is used in the subsequent treatment of the polarizing element and the transparent protective film. Examples of the adhesive include an isocyanate-based adhesive, a polyvinyl alcohol-based adhesive, a gelatin-based adhesive, an ethylene-based latex, and an aqueous polyester. The subsequent agent is usually used as an adhesive containing an aqueous solution, preferably containing 0.5% by weight to 60% by weight of a solid content component. In addition to the above, examples of the adhesive for the polarizing element and the transparent protective film include an ultraviolet curable adhesive, an electron beam curable adhesive, and the like. The electron beam hardening type adhesive exhibits an appropriate adhesion to the above various transparent protective films. Further, the adhesive used in the present invention may contain a metal compound filler.

The polarizing plate can be laminated with other optical films. Examples of the other optical film include a reflection plate, a reverse transmission plate, a phase difference plate (including a wave plate such as 1/2 or 1/4), a visual compensation film, and a brightness enhancement film, which may be formed in a liquid crystal display device or the like. The optical layer used in the process. These layers are laminated on a polarizing plate in practical use, and one layer or two or more layers can be used.

The optical film formed by laminating an optical layer on a polarizing plate can also be formed by sequentially laminating in a manufacturing process of a liquid crystal display device or the like. As such an optical film, an optical film is laminated in advance to have excellent quality stability, assembly work, and the like, and liquid crystal display can be exhibited. The manufacturing steps of the display device and the like are improved. Any appropriate attachment mechanism such as an adhesive layer can be used in the laminate. When the polarizing plate and the optical layer are adjacent to each other, the optical axes can be set to any appropriate arrangement angle according to the phase difference characteristics of the target or the like.

The optical member to which the adhesive layer of the present invention is applied can be preferably used in formation of various image display devices such as liquid crystal display devices. The formation of the liquid crystal display device can be performed based on the prior. In other words, the liquid crystal display device can be generally formed by arranging a polarizing plate with an adhesive layer on one side or both sides of a display panel such as a liquid crystal cell; and incorporating the components such as a lighting system as needed; Drive circuit. When the polarizing plate with the adhesive layer is disposed on both sides of the display panel, the same may be different. As the liquid crystal cell, for example, any appropriate type such as a TN type, an STN type, a π type, a VA type, or an IPS type can be employed.

When the liquid crystal display device is formed, one or two or more layers such as a diffusion plate, an anti-glare layer, an anti-reflection film, a protective plate, a tantalum array, a lens array sheet, a light diffusing plate, and a backlight may be disposed at any appropriate position. Any suitable part such as a device.

[Examples]

Hereinafter, the present invention will be specifically described by way of examples, but the present invention is not limited by the examples. Further, in the examples, "parts" and "%" are based on weight unless otherwise specified. Furthermore, "weight" can also be called "quality."

Furthermore, the meanings of the abbreviations in Table 1 are as follows.

BA: butyl acrylate (manufactured by Osaka Organic Chemical Industry Co., Ltd.)

AA: Acrylic (manufactured by Mitsubishi Chemical Corporation)

NVP: N-vinylpyrrolidone (manufactured by Nippon Shokubai Co., Ltd.)

HEA: Hydroxyethyl acrylate (manufactured by Osaka Organic Chemical Industry Co., Ltd.)

HBA: hydroxybutyl acrylate (manufactured by Osaka Organic Chemical Industry Co., Ltd.)

BzA: benzyl acrylate (manufactured by Osaka Organic Chemical Industry Co., Ltd.)

PEA: phenoxyethyl acrylate (manufactured by Osaka Organic Chemical Industry Co., Ltd.)

<Measurement of Weight Average Molecular Weight Mw>

The weight average molecular weight of the obtained (meth)acrylic polymer was measured by GPC (gel permeation chromatography). The sample was prepared by dissolving a sample in dimethylformamide to prepare a 0.1% by weight solution, and after allowing it to stand overnight, the filtrate was filtered through a 0.45 μm membrane filter.

‧Analytical device: manufactured by Tosoh Corporation, HLC-8120GPC

‧Tube: manufactured by Tosoh Corporation, Super AWM-H, AW4000, AW2500

‧ Column size: 6.0mm each ×150mm

‧ Dissolution: 30 mM lithium bromide, 30 mM-phosphoric acid dimethylformamide solution

‧Flow: 0.4ml/min

‧Detector: Differential Refractometer (RI)

‧column temperature: 40 ° C

‧Injection amount: 20μl

<Measurement of haze value>

The obtained adhesive sheet was attached to a micro-glass slide (thickness: 1.0 mmt to 1.2 mmt, manufactured by Songlang Glass Industrial Co., Ltd., part number S1112). The separator attached to one side of the adhesive sheet of the micro-slide was peeled off as described above, and was measured by a haze meter (HM-150, manufactured by Murakami Color Research Laboratory). The haze value of the adhesive layer.

<Appearance evaluation of optical members with adhesive layer>

The obtained polarizing plate with the adhesive layer was double-sidedly bonded to a 10-inch liquid crystal panel so as to be crossed nicol, and the backlight (B/L) was lit, and the appearance after the liquid crystal driving was visually observed. .

○‧‧‧ There is no problem in appearance

×‧‧‧Influence on appearance, problems

[Synthesis Example 1]

(Preparation of slip ring material solution)

Slide ring material manufactured by Advanced Soft Materials Co., Ltd. (SeRM (registered trademark) super polymer, part number: SH3400P) (linear molecule: polyethylene glycol, cyclic molecule: with hydroxypropyl and caprolactone) Chain α-cyclodextrin, blocking group: adamantyl group, weight average molecular weight (Mw) = 600,000, hydroxyl value = 72 mg KOH / g, solid content concentration of 100% by mass) mixed with ethyl acetate, will The temperature was adjusted to 50 ° C and dissolved while stirring for 60 minutes to prepare an 11% by weight ethyl acetate solution of the slip ring material.

[Example 1]

(Preparation of acrylic polymer)

In a reaction vessel having a stirrer, a thermometer, a reflux condenser, and a nitrogen introduction tube, a monomer blended at a blending ratio (weight ratio) shown in Table 1 was charged: 100 parts by weight, ethyl acetate: 200 weight And 2,2'-azobisisobutyronitrile: 0.1 part by weight, the air in the reaction vessel was replaced by nitrogen. Thereafter, the reaction solution was heated to 60 ° C while stirring in a nitrogen atmosphere, and allowed to react for 12 hours, followed by cooling to room temperature. Thereby, an ethyl acetate solution of the acrylic polymer (1) having a weight average molecular weight (Mw) = 2.04 million was obtained. Further, ethyl acetate was added to the ethyl acetate solution of the obtained acrylic polymer (1), and the solid content of the acrylic polymer (1) was diluted to 12% by weight to obtain an acrylic polymer (1). Ethyl acetate solution (solid content = 12% by weight).

(Manufacture of adhesive composition)

An 11% by weight ethyl acetate solution of the slip ring material obtained in Synthesis Example 1 and an ethyl acetate solution (solid content = 12% by weight) of the acrylic polymer (1) were used to obtain an acrylic polymer (1)/ The slip ring material was adjusted to a ratio of 90/10 (weight ratio) in a reaction vessel, and stirred and mixed by a stirrer. Then, 0.6 parts by weight of an isocyanate crosslinking agent (CORONATE HX, Nippon Polyurethane) is added to 100 parts by weight of the total solid content of the acrylic polymer (1) and the slip ring material in the reaction container. Stirring was carried out again to obtain an adhesive composition (1).

(Manufacture of adhesive layer and adhesive sheet)

The adhesive composition (1) was applied to a polyethylene terephthalate (PET) film (Mitsubishi Chemical Polyester Film Co., Ltd.) subjected to polyfluorination treatment so that the thickness of the dried adhesive layer became 23 μm. The single side of MRF38) was dried at 155 ° C for 1 minute to form an adhesive sheet (1) having an adhesive layer (1).

The results are shown in Table 1.

(Manufacture of optical member with adhesive layer)

The polyvinyl alcohol film having a thickness of 80 μm was dyed for one minute in a 0.3% iodine solution at 30° C., and stretched three times between rolls having different speed ratios. Thereafter, the mixture was immersed for 0.5 minute in an aqueous solution containing 4% of boric acid and 10% of potassium iodide at 60 ° C until the total stretching ratio was 6 times. Next, the mixture was immersed in an aqueous solution containing potassium iodide at a concentration of 1.5% at 30 ° C for 10 seconds to be washed, and then dried at 50 ° C for 4 minutes to obtain a polarizing element. A polarizing plate was prepared by laminating a saponified triacetyl cellulose film having a thickness of 80 μm on both sides of the obtained polarizing element by a polyvinyl alcohol-based adhesive. Further, a polarizing plate (B) was produced in the same manner as described above except that an acrylic film (lactone-modified acrylic resin film) having a thickness of 30 μm was used instead of the triacetyl cellulose film having a thickness of 80 μm. Also, use a thickness of 60 μm An olefin film (ZEONOR FILM ZB12, manufactured by ZEON Co., Ltd.) was used instead of the triacetyl cellulose film having a thickness of 80 μm, and a polarizing plate (C) was produced in the same manner as above. Next, the adhesive layer (1) is transferred from the adhesive sheet (1) to each of the polarizing plates (A) to (C) to form a polarizing plate (1A) to (1C) with an adhesive layer. The polarizing plate (1A) with an adhesive layer is obtained by moving the adhesive layer (1) from the adhesive sheet (1) to the polarizing plate (A). The polarizing plate (1B) with an adhesive layer is obtained by moving the adhesive layer (1) from the adhesive sheet (1) to the polarizing plate (B). The polarizing plate (1C) with an adhesive layer is obtained by moving the adhesive layer (1) from the adhesive sheet (1) to the polarizing plate (C).

The results are shown in Table 1.

[Embodiment 2]

(Preparation of acrylic polymer)

An acrylic polymer having a weight average molecular weight (Mw) of 2,000,000 was obtained in the same manner as in Example 1 except that the monomer was blended in the blending ratio (weight ratio) shown in Table 1 (2). Ethyl acetate solution. Further, ethyl acetate was added to the ethyl acetate solution of the obtained acrylic polymer (2), and the solid content of the acrylic polymer (2) was diluted to 12% by weight to obtain an acrylic polymer (2). Ethyl acetate solution (solid content = 12% by weight).

(Manufacture of adhesive composition)

An ethyl acetate solution (solid content = 12% by weight) of the acrylic polymer (2) was used instead of the ethyl acetate solution (solid content = 12% by weight) of the acrylic polymer (1), and Example 1 was carried out in the same manner to obtain an adhesive composition (2).

(Manufacture of adhesive layer and adhesive sheet)

The obtained adhesive composition (2) was applied to a separator (manufactured by Mitsubishi Chemical Polyester Film Co., Ltd., MRF38) by an applicator so as to have a film thickness of 23 μm after drying, and was adjusted to 155. The solvent was dried in an oven at ° C for 1 minute to prepare an adhesive sheet (2) having an adhesive layer (2).

The results are shown in Table 1.

(Manufacture of optical member with adhesive layer)

A polarizing plate (2A) to (2C) with an adhesive layer was produced in the same manner as in Example 1 except that the adhesive layer (2) was used instead of the adhesive layer (1). The polarizing plate (2A) with an adhesive layer is obtained by moving the adhesive layer (2) from the adhesive sheet (2) to the polarizing plate (A). The polarizing plate (2B) with an adhesive layer is obtained by moving the adhesive layer (2) from the adhesive sheet (2) to the polarizing plate (B). The polarizing plate (2C) with an adhesive layer is obtained by moving the adhesive layer (2) from the adhesive sheet (2) to the polarizing plate (C).

The results are shown in Table 1.

[Example 3]

(Preparation of acrylic polymer)

An acrylic polymer having a weight average molecular weight (Mw) = 920,000 was obtained in the same manner as in Example 1 except that the monomer was blended in the blending ratio (weight ratio) shown in Table 1 (3). Ethyl acetate solution. Further, ethyl acetate was added to the ethyl acetate solution of the obtained acrylic polymer (3), and the solid content of the acrylic polymer (3) was diluted to 12% by weight to obtain an acrylic polymer (3). Ethyl acetate solution (solid content = 12% by weight).

(Manufacture of adhesive composition)

An ethyl acetate solution (solid content = 12% by weight) of the acrylic polymer (3) was used instead of the ethyl acetate solution (solid content = 12% by weight) of the acrylic polymer (1), and Example 1 was carried out in the same manner to obtain an adhesive composition (3).

(Manufacture of adhesive layer and adhesive sheet)

The obtained adhesive composition (3) was applied to a separator (manufactured by Mitsubishi Chemical Polyester Film Co., Ltd., MRF38) by an applicator so that the film thickness after drying became 23 μm, and was adjusted to 155. The solvent was dried in an oven at ° C for 1 minute to prepare an adhesive sheet (3) having an adhesive layer (3).

The results are shown in Table 1.

(Manufacture of optical member with adhesive layer)

A polarizing plate (3A) to (3C) with an adhesive layer was produced in the same manner as in Example 1 except that the adhesive layer (3) was used instead of the adhesive layer (1). The polarizing plate (3A) with an adhesive layer is obtained by moving the adhesive layer (3) from the adhesive sheet (3) to the polarizing plate (A). The polarizing plate (3B) with an adhesive layer is obtained by moving the adhesive layer (3) from the adhesive sheet (3) to the polarizing plate (B). The polarizing plate (3C) with an adhesive layer is obtained by moving the adhesive layer (3) from the adhesive sheet (3) to the polarizing plate (C).

The results are shown in Table 1.

[Comparative Example 1]

(Preparation of acrylic polymer)

An acrylic polymer (C1) having a weight average molecular weight (Mw) of 2.2 million was obtained in the same manner as in Example 1 except that the monomer to be blended in the blending ratio (weight ratio) shown in Table 1 was used. Ethyl acetate solution. Further, ethyl acetate was added to the ethyl acetate solution of the obtained acrylic polymer (C1), and the solid content of the acrylic polymer (C1) was diluted to 12% by weight to obtain an acrylic polymer (C1). Ethyl acetate solution (solid content = 12% by weight).

(Manufacture of adhesive composition)

An ethyl acetate solution (solid content = 12% by weight) of the acrylic polymer (C1) was used instead of the ethyl acetate solution (solid content = 12% by weight) of the acrylic polymer (1), and Example 1 was carried out in the same manner to obtain an adhesive composition (C1).

(Manufacture of adhesive layer and adhesive sheet)

The obtained adhesive composition (C1) was applied to a separator (manufactured by Mitsubishi Chemical Polyester Film Co., Ltd., MRF38) by an applicator so as to have a film thickness of 23 μm after drying, and was adjusted to 155. The solvent was dried in an oven at ° C for 1 minute to prepare an adhesive sheet (C1) having an adhesive layer (C1).

The results are shown in Table 1.

(Manufacture of optical member with adhesive layer)

A polarizing plate (C1A) to (C1C) with an adhesive layer was produced in the same manner as in Example 1 except that the adhesive layer (C1) was used instead of the adhesive layer (1). The polarizing plate (C1A) with an adhesive layer is obtained by moving the adhesive layer (C1) from the adhesive sheet (C1) to the polarizing plate (A). The polarizing plate (C1B) with an adhesive layer is obtained by moving the adhesive layer (C1) from the adhesive sheet (C1) to the polarizing plate (B). The polarizing plate (C1C) with an adhesive layer is obtained by moving the adhesive layer (C1) from the adhesive sheet (C1) to the polarizing plate (C).

The results are shown in Table 1.

[Comparative Example 2]

(Preparation of acrylic polymer)

An acrylic polymer (C2) having a weight average molecular weight (Mw) of 1.6 million was obtained in the same manner as in Example 1 except that the monomer having the blending ratio (weight ratio) shown in Table 1 was used. Ethyl acetate solution. Further, ethyl acetate was added to the ethyl acetate solution of the obtained acrylic polymer (C2), and the solid content of the acrylic polymer (C2) was diluted to 12% by weight to obtain an acrylic polymer (C2). Ethyl acetate solution (solid content = 12% by weight).

(Manufacture of adhesive composition)

An ethyl acetate solution (solid content = 12% by weight) of the acrylic polymer (C2) was used instead of the ethyl acetate solution (solid content = 12% by weight) of the acrylic polymer (1), and Example 1 was carried out in the same manner to obtain an adhesive composition (C2).

(Manufacture of adhesive layer and adhesive sheet)

The obtained adhesive composition (C2) was applied to a separator (manufactured by Mitsubishi Chemical Polyester Film Co., Ltd., MRF38) by an applicator so as to have a film thickness of 23 μm after drying, and was adjusted to 155. The solvent was dried in an oven at ° C for 1 minute to prepare an adhesive sheet (C2) having an adhesive layer (C2).

The results are shown in Table 1.

(Manufacture of optical member with adhesive layer)

A polarizing plate (C2A) to (C2C) with an adhesive layer was produced in the same manner as in Example 1 except that the adhesive layer (C2) was used instead of the adhesive layer (1). The polarizing plate (C2A) with an adhesive layer is obtained by moving the adhesive layer (C2) from the adhesive sheet (C2) to the polarizing plate (A). The polarizing plate (C2B) with an adhesive layer is obtained by moving the adhesive layer (C2) from the adhesive sheet (C2) to the polarizing plate (B). The polarizing plate (C2C) with an adhesive layer is obtained by moving the adhesive layer (C2) from the adhesive sheet (C2) to the polarizing plate (C).

The results are shown in Table 1.

[Comparative Example 3]

(Preparation of acrylic polymer)

An acrylic polymer (C3) having a weight average molecular weight (Mw) of 1 to 100,000 was obtained in the same manner as in Example 1 except that the monomer to be blended in the blending ratio (weight ratio) shown in Table 1 was used. Ethyl acetate solution. Further, ethyl acetate was added to the ethyl acetate solution of the obtained acrylic polymer (C3), and the solid content of the acrylic polymer (C3) was diluted to 12% by weight to obtain an acrylic polymer (C3). Ethyl acetate solution (solid content = 12% by weight).

(Manufacture of adhesive composition)

An ethyl acetate solution (solid content = 12% by weight) of the acrylic polymer (C3) was used instead of the ethyl acetate solution (solid content = 12% by weight) of the acrylic polymer (1), and Example 1 was carried out in the same manner to obtain an adhesive composition (C3).

(Manufacture of adhesive layer and adhesive sheet)

The obtained adhesive composition (C3) was applied to a separator (manufactured by Mitsubishi Chemical Polyester Film Co., Ltd., MRF38) by an applicator so as to have a film thickness of 23 μm after drying, and was adjusted to 155. The solvent was dried in an oven at ° C for 1 minute to prepare an adhesive sheet (C3) having an adhesive layer (C3).

The results are shown in Table 1.

(Manufacture of optical member with adhesive layer)

A polarizing plate (C3A) to (C3C) with an adhesive layer was produced in the same manner as in Example 1 except that the adhesive layer (C3) was used instead of the adhesive layer (1). The polarizing plate (C3A) with an adhesive layer is obtained by moving the adhesive layer (C3) from the adhesive sheet (C3) to the polarizing plate (A). The polarizing plate (C3B) with an adhesive layer is obtained by moving the adhesive layer (C3) from the adhesive sheet (C3) to the polarizing plate (B). The polarizing plate (C3C) with an adhesive layer is obtained by moving the adhesive layer (C3) from the adhesive sheet (C3) to the polarizing plate (C).

The results are shown in Table 1.

[Comparative Example 4]

(Preparation of acrylic polymer)

An acrylic polymer (C4) having a weight average molecular weight (Mw) of 950,000 was obtained in the same manner as in Example 1 except that the monomer was blended in the blending ratio (weight ratio) shown in Table 1. Ethyl acetate solution. Further, ethyl acetate was added to the ethyl acetate solution of the obtained acrylic polymer (C4), and the solid content of the acrylic polymer (C4) was diluted to 12% by weight to obtain an acrylic polymer (C4). Ethyl acetate solution (solid content = 12% by weight).

(Manufacture of adhesive composition)

An ethyl acetate solution (solid content = 12% by weight) of the acrylic polymer (C4) was used instead of the ethyl acetate solution (solid content = 12% by weight) of the acrylic polymer (1), and Example 1 was carried out in the same manner to obtain an adhesive composition (C4).

(Manufacture of adhesive layer and adhesive sheet)

The obtained adhesive composition (C4) was applied to a separator (manufactured by Mitsubishi Chemical Polyester Film Co., Ltd., MRF38) by an applicator so as to have a film thickness of 23 μm after drying, and was adjusted to 155. The solvent was dried in an oven at ° C for 1 minute to prepare an adhesive sheet (C4) having an adhesive layer (C4).

The results are shown in Table 1.

(Manufacture of optical member with adhesive layer)

A polarizing plate (C4A) to (C4C) with an adhesive layer was produced in the same manner as in Example 1 except that the adhesive layer (C4) was used instead of the adhesive layer (1). The polarizing plate (C4A) with an adhesive layer is obtained by moving the adhesive layer (C4) from the adhesive sheet (C4) to the polarizing plate (A). The polarizing plate (C4B) with an adhesive layer is obtained by moving the adhesive layer (C4) from the adhesive sheet (C4) to the polarizing plate (B). The polarizing plate (C4C) with an adhesive layer is obtained by moving the adhesive layer (C4) from the adhesive sheet (C4) to the polarizing plate (C).

The results are shown in Table 1.

[Comparative Example 5]

(Preparation of acrylic polymer)

An acrylic polymer (C5) having a weight average molecular weight (Mw) = 840,000 was obtained in the same manner as in Example 1 except that the monomer to be blended in the blending ratio (weight ratio) shown in Table 1 was used. Ethyl acetate solution. Further, ethyl acetate was added to the ethyl acetate solution of the obtained acrylic polymer (C5), and the solid content of the acrylic polymer (C5) was diluted to 12% by weight to obtain an acrylic polymer (C5). Ethyl acetate solution (solid content = 12% by weight).

(Manufacture of adhesive composition)

An ethyl acetate solution (solid content = 12% by weight) of an acrylic polymer (C5) was used instead of the ethyl acetate solution (solid content = 12% by weight) of the acrylic polymer (1), and Example 1 was carried out in the same manner to obtain an adhesive composition (C5).

(Manufacture of adhesive layer and adhesive sheet)

The obtained adhesive composition (C5) was applied to a separator (manufactured by Mitsubishi Chemical Polyester Film Co., Ltd., MRF38) by an applicator so as to have a film thickness of 23 μm after drying, and was adjusted to 155. The solvent was dried in an oven at ° C for 1 minute to prepare an adhesive sheet (C5) having an adhesive layer (C5).

The results are shown in Table 1.

(Manufacture of optical member with adhesive layer)

A polarizing plate (C5A) to (C5C) with an adhesive layer was produced in the same manner as in Example 1 except that the adhesive layer (C5) was used instead of the adhesive layer (1). The polarizing plate (C5A) with an adhesive layer is obtained by moving the adhesive layer (C5) from the adhesive sheet (C5) to the polarizing plate (A). The polarizing plate (C5B) with an adhesive layer is obtained by moving the adhesive layer (C5) from the adhesive sheet (C5) to the polarizing plate (B). The polarizing plate (C5C) with an adhesive layer is obtained by moving the adhesive layer (C5) from the adhesive sheet (C5) to the polarizing plate (C).

The results are shown in Table 1.

[Reference Example 1]

(Preparation of acrylic polymer)

An acrylic polymer (R1) having a weight average molecular weight (Mw) = 2.04 million was obtained in the same manner as in Example 1 except that the monomer to be blended in the blending ratio (weight ratio) shown in Table 1 was used. Ethyl acetate solution. Further, ethyl acetate was added to the ethyl acetate solution of the obtained acrylic polymer (R1), and the solid content of the acrylic polymer (R1) was diluted to 12% by weight to obtain an acrylic polymer (R1). Ethyl acetate solution (solid content = 12% by weight).

(Manufacture of adhesive composition)

The sliding polymer material obtained in Synthesis Example 1 was not used, and the acrylic polymer (1) was directly used as the adhesive composition (R1).

(Manufacture of adhesive layer and adhesive sheet)

The obtained adhesive composition (R1) was applied to a separator (manufactured by Mitsubishi Chemical Polyester Film Co., Ltd., MRF38) by an applicator so as to have a film thickness of 23 μm after drying, and was adjusted to 155. The solvent was dried in an oven at ° C for 1 minute to prepare an adhesive sheet (R1) having an adhesive layer (R1).

The results are shown in Table 1.

(Manufacture of optical member with adhesive layer)

A polarizing plate (R1A) to (R1C) with an adhesive layer was produced in the same manner as in Example 1 except that the pressure-sensitive adhesive layer (R1) was used instead of the pressure-sensitive adhesive layer (1). The polarizing plate (R1A) with an adhesive layer is obtained by moving the adhesive layer (R1) from the adhesive sheet (R1) to the polarizing plate (A). The polarizing plate (R1B) with an adhesive layer is obtained by moving the adhesive layer (R1) from the adhesive sheet (R1) to the polarizing plate (B). The polarizing plate (R1C) with an adhesive layer is obtained by moving the adhesive layer (R1) from the adhesive sheet (R1) to the polarizing plate (C).

The results are shown in Table 1.

[Table 1]

According to the results of Table 1, it is understood that the haze can be greatly suppressed by containing a monomer having an aromatic ring structure in an optimum composition. Moreover, it was confirmed that the appearance evaluation was improved to be approximately the same as the state in which the material of the slip ring was not placed.

[Industrial availability]

The adhesive composition, the adhesive layer, the adhesive sheet, the optical member with the adhesive layer of the present invention, and the image display device can be utilized, for example, in the field of optics.

Claims (11)

An adhesive composition comprising a (meth)acrylic polymer and a polyrotaxane, wherein the polyrotaxane has a cyclic molecule, a linear molecule penetrating through an opening of the cyclic molecule, and a blocking group which is disposed at both ends of the linear molecule so as not to be detached from the linear molecule, and the (meth)acrylic polymer contains a monomer derived from a structure having no aromatic ring structure The structural unit and the structural unit derived from a monomer having an aromatic ring structure. The adhesive composition according to claim 1, wherein the content ratio of the (meth)acrylic polymer in the adhesive composition is 70% by weight to 98% by weight based on the weight ratio. The adhesive composition according to claim 1, wherein the content ratio of the above polyrotaxane in the above adhesive composition is from 2% by weight to 30% by weight based on the weight ratio. The adhesive composition according to claim 2, wherein the content ratio of the above polyrotaxane in the above adhesive composition is from 2% by weight to 30% by weight based on the weight ratio. The adhesive composition according to any one of claims 1 to 4, wherein a content ratio of the structural unit derived from the monomer having an aromatic ring structure in the (meth)acrylic polymer is 1% by weight to 35% by weight. The adhesive composition according to any one of claims 1 to 4, wherein the monomer having an aromatic ring structure contains at least one selected from the group consisting of benzyl acrylate and phenoxyethyl acrylate. The adhesive composition according to claim 5, wherein the monomer having an aromatic ring structure contains at least one selected from the group consisting of benzyl acrylate and phenoxyethyl acrylate. An adhesive layer comprising the adhesive composition of any one of claims 1 to 7. An adhesive sheet comprising the adhesive layer and the substrate layer of claim 8. An optical member with an adhesive layer comprising the adhesive layer of claim 8 and an optical member. An image display device comprising at least one optical member such as the adhesive layer of claim 10.