CN106795407A - Polarizer adhesive composition, bonding sheet, polarizer and layered product with adhesive phase - Google Patents
Polarizer adhesive composition, bonding sheet, polarizer and layered product with adhesive phase Download PDFInfo
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- CN106795407A CN106795407A CN201580054308.7A CN201580054308A CN106795407A CN 106795407 A CN106795407 A CN 106795407A CN 201580054308 A CN201580054308 A CN 201580054308A CN 106795407 A CN106795407 A CN 106795407A
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- polarizer
- methyl
- adhesive phase
- adhesive
- adhesive composition
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
-
- 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
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
-
- 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
-
- 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
- C09J7/10—Adhesives in the form of films or foils without carriers
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/10—Optical coatings produced by application to, or surface treatment of, optical elements
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/30—Polarising elements
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- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Adhesive Tapes (AREA)
- Liquid Crystal (AREA)
- Laminated Bodies (AREA)
Abstract
It is excellent and possess the polarizer adhesive composition of the adhesive phase of hot and humid lower durability that the present invention provides a kind of antistatic performance that can be formed.The polarizer adhesive composition contains：(A) (methyl) acrylic polymer, (B) crosslinking agent and (C) anion as obtained by the polymerizable monomer polymerization with polyoxyalkylenes or (methyl) acrylate (a1) of alkoxyalkyl comprising more than 41 mass % are selected from N, double (fluorine sulphonyl) imines of N and double (trifluoro methylsulfonyl) imines of N, N, cation are the ionic compound of organic cation and fusing point more than 25 DEG C.
Description
Technical field
The present invention relates to polarizer adhesive composition, bonding sheet, polarizer and layered product with adhesive phase.
Background technology
In recent years, liquid crystal cell vehicle-mounted, outdoor instrument use or display, the television set etc. of PC on use
Way constantly expands, and use environment also becomes very harsh therewith.Liquid crystal cell has liquid crystal material by two pieces of substrate (such as glass
Plate) clamped by structure, polarizer adheres to the surface of the substrate via adhesive phase.It is therefore desirable to described adhesive layer
Also there is the durability under hot and humid heat.
When liquid crystal cell is manufactured, polarizer adhesive phase is generally stained with the cover layer that lift-off processing is crossed in one side
It is pasted on polarizer under state, then, peels off cover layer and expose adhesive phase, then be attached on substrate.Now, by
It is high in the insulating properties of cover layer or polarizer and produce electrostatic, upset liquid crystal aligning can be produced, the bad shadows such as electronic unit are damaged
Ring.
It is therefore desirable to polarizer adhesive phase also has antistatic performance, as the polarizer with antistatic performance
With adhesive phase, the technology containing ionic compound in the adhesive composition for making to be formed adhesive phase is reported.
For example, recorded in patent document 1 containing the acrylic resin as obtained by specific (methyl) acrylic ester polymerization,
It is with organic cation and at room temperature the ionic compound and the adhesive composition of crosslinking agent of solid.In patent document 2
Describe and contain ionic compound of the fusing point more than 50 DEG C, the matrix polymer with less than 0 DEG C of glass transition temperature
Adhesive composition.
Prior art literature
Patent document
Patent document 1：Japanese Patent Laid-Open 2010-66756 publications
Patent document 2：Japanese Patent Laid-Open 2009-19162 publications
The content of the invention
The technical problems to be solved by the invention
Polarizer generally has for protecting polarizer (Japanese mostly：Polarisation) diaphragm.Adhesive phase and institute
Diaphragm is stated to connect and formed.However, according to the research of the present inventor, finding under hygrothermal environment, by institute in adhesive phase
Comprising ionic compound, can produce the component of polymer for constituting the diaphragm that hydrolysis, corrosion polarizer etc. occur long-term
The problem of reliability.Further, since the further filming of part uses extensiveization of scope in recent years, it is desirable to than so far
Untill long term test it is harsher under conditions of also there is no above mentioned problem.
It is excellent and possess hot and humid that the technical problems to be solved by the invention are that offer can form antistatic performance
The polarizer adhesive composition of the adhesive phase of lower durability, the bonding with the adhesive phase formed by above-mentioned composition
Piece, the polarizer with adhesive phase with above-mentioned adhesive phase and the layered product with above-mentioned adhesive phase.
Solve the technical scheme that technical problem is used
The present inventor has made intensive studies to solve above-mentioned technical problem.Result discovery, will contain specified quantitative
(methyl) acrylic polymer, crosslinking agent and specific ion as obtained by the polymerizable monomer of specific (methyl) acrylate
Under the occasion of compound, above-mentioned technical problem is can solve the problem that, so as to complete the present invention.
The present invention is, for example, following [1]~[6].
[1] a kind of polarizer adhesive composition, it contains：
(A) comprising more than 41 mass % by (methyl) acrylate (a1) with polyoxyalkylenes or alkoxyalkyl
Polymerizable monomer polymerization obtained by (methyl) acrylic polymer,
(B) crosslinking agent and
(C) anion is selected from N, and double (fluorine sulphonyl) imines of N- and double (trifluoro methylsulfonyl) imines of N, N-, cation are organic
The ionic compound of cation and fusing point more than 25 DEG C.
[2] the polarizer adhesive composition as described in [1], wherein, also contain silane coupler (D).
[3] the polarizer adhesive composition as described in [1] or [2], wherein, in ionic compound (C), it is organic sun from
Son is the tetraalkylammonium cation represented with formula (c-1),
In formula (c-1), R1、R2、R3And R4It is separately alkyl.
[4] a kind of polarizer bonding sheet, it has the polarizer adhesive group as any one of [1]~[3]
The adhesive phase that compound is formed.
[5] a kind of polarizer with adhesive phase, its have polarizer and at least one side of the polarizer by
[1] adhesive phase that the polarizer any one of~[3] is formed with adhesive composition.
[6] a kind of layered product, wherein, polarizer has the diaphragm of polarizer and configuration on the polarizer,
The layered product is combined by the polarizer, the diaphragm, the polarizer any one of [1]~[3] with adhesive
The adhesive phase and glass substrate that thing is formed are laminated in this order.
The effect of invention
By means of the invention it is possible to it is excellent and possess the inclined of the adhesive phase of hot and humid lower durability to form antistatic performance
Shake piece adhesive composition, the bonding sheet with the adhesive phase formed by above-mentioned composition, with above-mentioned adhesive phase
Polarizer with adhesive phase and the layered product with above-mentioned adhesive phase.
Specific embodiment
Below, to polarizer adhesive composition of the invention, polarizer bonding sheet, the polarization with adhesive phase
Piece and layered product are illustrated.Hereinafter, polarizer adhesive composition of the invention is also referred to as " adhesive group
Compound ", polarizer bonding sheet of the invention is also referred to as " bonding sheet ".
Acrylic acid and methacrylic acid are referred to as in this specification and are denoted as " (methyl) acrylic acid ".
[polarizer adhesive composition]
Polarizer adhesive composition of the invention contains (methyl) acrylic polymer (A) as described below, hands over
Connection agent (B) and ionic compound (C).Above-mentioned adhesive composition can also contain silane coupler (D) as needed, or also
Organic solvent (E) can be contained.
[(methyl) acrylic compounds polymers (A)]
(methyl) acrylic polymer (A) is comprising with polyoxyalkylenes or alkoxyalkyl (methyl) acrylic acid
The polymer of the polymerizable monomer of ester (a1), is polymerized by above-mentioned polymer monomer and is obtained.Thus, (methyl) acrylic polymer
(A) preferably there is the construction unit for coming from (a1).
Both can only be with polyoxyalkylenes or alkoxyalkyl (methyl) acrylic acid as above-mentioned polymerizable monomer
Ester (a1), it is also possible to also comprising selected from without polyoxyalkylenes, alkoxyalkyl and crosslinking while comprising above-mentioned (a1)
(methyl) acrylate (a2) of any one in property group, the monomer (a3) containing crosslinkable groups, and other monomers (a4)
In at least one.For example, can enumerate comprising above-mentioned (a1)~(a3) and according to the necessary also polymerism list comprising above-mentioned (a4)
Body.
Here, the crosslinkable groups are to refer to be imported to (methyl) acrylic polymer (A) handed over by crosslinking agent (B)
The group of the crosslinking points that connection is obtained, can enumerate hydroxyl, carboxyl etc..
Hereinafter, described (methyl) acrylate (a1) is also referred to as " monomer (a1) ", (methyl) acrylate (a2)
Also referred to as " monomer (a2) ", the monomer (a3) containing crosslinkable groups is also referred to as " monomer (a3) ", and other monomers (a4) are also referred to as
" monomer (a4) ".
《Monomer (a1)》
Monomer (a1) is with polyoxyalkylenes or alkoxyalkyl (methyl) acrylate.Monomer (a1) is preferably not
(methyl) acrylate containing crosslinkable groups.
Monomer (a1) can for example be represented with formula (a-1).
CH2=CR1-COOR2···(a-1)
R1It is hydrogen atom or methyl, R2It is the group represented with formula (g-1).
-(R3O)nR4···(g-1)
R3It is alkylidene, R4It is alkyl, n is more than 1 integer.The carbon number of alkylidene is usually 1~10, preferably 1~5.
The carbon number of alkyl is usually 1~10, preferably 1~4.N is preferably 1~20, more preferably 1~4, more preferably 1~2.
As monomer (a1), such as (methyl) alkyl acrylate epoxide alkyl ester, single (methyl) alkyl acrylate epoxide can be enumerated many
Alkylene glycols ester.
As (methyl) alkyl acrylate epoxide alkyl ester, such as (methyl) methoxyethyl methyl esters, (methyl) third can be enumerated
Olefin(e) acid 2- methoxy acrylates, (methyl) acrylic acid 2- ethoxy ethyl esters, (methyl) acrylic acid 3- methoxyl groups propyl ester, (methyl) propylene
Sour 3- ethyoxyls propyl ester, (methyl) acrylic acid 4- methoxybutyls, (methyl) acrylic acid 4- Ethoxybutyls.
As many alkylene glycols esters of list (methyl) alkyl acrylate epoxide, for example single (methyl) methoxyethyl two can be enumerated
Glycol ester, list (methyl) methoxyethyl DPG ester, single (methyl) ethioxy triglycol ester, single (first
Base) ethioxy binaryglycol ester, singly (methyl) methoxyethyl triglycol ester.
As monomer (a1), from from the viewpoint of reactivity, the R of preferred formula (a-1) in above-mentioned substance2It is alkoxyalkyl
(methyl) alkoxyalkyl acrylate.
Monomer (a1) both can be used alone one kind, it is possible to use two or more.
In the mass % of polymerizable monomer 100 for forming (methyl) acrylic polymer (A), the consumption of monomer (a1) exists
More than 41 mass %, preferably in more than 50 mass %, more preferably 60~99.3 mass %.
If the consumption of monomer (a1) is in more than 41 mass %, by viscous containing (methyl) acrylic polymer (A)
The adhesive phase that mixture composite is formed show it is highly polar, and to the adaptation of polarizer and substrate (particularly glass plate) etc.
It is excellent.Therefore, even if in the case where high temperature, height are damp and hot, tilting, peeling of the adhesive phase from polarizer or substrate etc. will not also occur
Deng the adhesive phase of excellent in te pins of durability can be formed.Further, since the excellent adhesion with base material, therefore doing over again property (リ ワ ー
Network) it is good, so that adhesive phase is not susceptible to the adhesion to piercing tip (beating Chi order I sword), surrounding polarizer etc., operation
Property is excellent.If the consumption of monomer (a1) is in more than 50 mass %, the effect above is more significantly.If the consumption of monomer (a1)
Within the above range, then (methyl) acrylic polymer (A) is good with the compatibility of ionic compound (C) hereinafter described, energy
Enough suppress oozing out for ionic compound (C).
《Monomer (a2)》
Monomer (a2) is without (methyl) third of any one in polyoxyalkylenes, alkoxyalkyl and crosslinkable groups
Olefin(e) acid ester.(methyl) acrylic polymer (A) preferably has the construction unit for coming from (a2).
Monomer (a2) can for example be represented with formula (a-2).
CH2=CR5-COOR6···(a-2)
R5It is hydrogen atom or methyl, R6Be without in polyoxyalkylenes, alkoxyalkyl and crosslinking group any one have
Machine group.
As R6Represented organic group, can enumerate the ester ring type group such as alkyl, cycloalkyl, aryl, aralkyl, fragrant oxygen
Base alkyl, aminoalkyl of N- monoalkyls substitution etc..The carbon number of alkyl is usually 1~24.The carbon of the ester ring type group such as cycloalkyl
Number is usually 3~15.The carbon number of aryl is usually 6~10.Aralkyl generally by alkylidene that carbon number is 1~6 and carbon number be 6~
10 aryl is constituted.Aryloxy alkyl is generally made up of the oxyalkylene group that carbon number is 1~6 and the aryl that carbon number is 6~10.N- is mono-
The carbon number of alkyl-substituted aminoalkyl is usually 1~12.
As monomer (a2), such as (methyl) alkyl acrylate, (methyl) acrylate base ester etc. can be enumerated and contained
(methyl) acrylate of ester ring type group, (methyl) benzyl acrylate, (methyl) acrylic acid aralkyl ester, (methyl) propylene
(methyl) acrylate of sour aryloxy group alkyl base ester, the aminoalkyl containing the substitution of N- monoalkyls.
As (methyl) alkyl acrylate, such as (methyl) acrylate methyl esters, (methyl) acrylic acid second can be enumerated
Ester, (methyl) n-propyl, (methyl) isopropyl acrylate, (methyl) propylene N-butyl, (methyl) isobutyl acrylate,
(methyl) tert-butyl acrylate, (methyl) acrylic acid n-pentyl ester, (methyl) the just own ester of acrylic acid, the positive heptyl ester of (methyl) acrylic acid,
(methyl) 2-EHA, (methyl) n-octyl, (methyl) Isooctyl acrylate monomer, the positive nonyl of (methyl) acrylic acid
Ester, the different nonyl ester of (methyl) acrylic acid, the positive last of the ten Heavenly stems ester of (methyl) acrylic acid, (methyl) isodecyl acrylate, (methyl) acrylic acid 11
Arrcostab, (methyl) dodecylacrylate, (methyl) octadecyl acrylate, (methyl) acrylic acid isooctadecane base
Ester.
(methyl) acrylate containing ester ring type group, (methyl) acrylic acid as (methyl) acrylate base ester etc.
Aryl ester and (methyl) acrylic acid aralkyl ester, can enumerate such as (methyl) cyclohexyl acrylate, the different ice of (methyl) acrylic acid
Piece ester, (methyl) phenyl acrylate, (methyl) benzyl acrylate.
As (methyl) acrylic acid aryloxy group alkyl base ester, such as (methyl) acrylic acid phenoxy group methyl esters, (methyl) can be enumerated
Acrylic acid 2- phenoxy ethyls, (methyl) acrylic acid 2- toloxyls ethyl ester, (methyl) acrylic acid xylyloxy methyl esters, (first
Base) acrylic acid naphthoxy methyl esters.
As (methyl) acrylate for the aminoalkyl replaced containing N- monoalkyls, such as (methyl) acrylic acid can be enumerated
Monomethylaminoethylester, (methyl) acrylic acid list ethylamino ethyl ester, (methyl) acrylic acid mono-methyl amino propyl ester, (methyl) third
Olefin(e) acid list ethylamino propyl ester.
Monomer (a2) both can be used alone one kind, it is possible to use two or more.
In the mass % of polymerizable monomer 100 for forming (methyl) acrylic polymer (A), the consumption of monomer (a2) is excellent
Choosing is less than 59 mass %, more preferably more preferably 0.2~49.9 mass %, 0.5~39.8 mass %.
《Monomer (a3)》
Monomer (a3) is the monomer containing crosslinkable groups.(methyl) acrylic polymer (A) can also have come from
(a3) construction unit.
As the polymerizable monomer for constituting (methyl) acrylic polymer (A), can be come to (first by using monomer (a3)
Base) acrylic polymer (A) imported by crosslinking agent (B) crosslinking points that obtain of crosslinking.
Monomer (a3) can for example be represented with formula (a-3).
CH2=CR7-COOR8···(a-3)
R7It is hydrogen atom or methyl, R8It is the organic group with crosslinkable groups.As the crosslinkable groups, can example
Lift hydroxyl, carboxyl etc..
As R8Represented organic group, can enumerate the aliphatic group of hydroxyalkyl, the carboxyl substitution that carbon number is 1~12
Deng.
As monomer (a3), (methyl) acrylate for example containing hydroxyl, (methyl) propylene containing carboxyl can be enumerated
Acid esters.
As (methyl) acrylate containing hydroxyl, (methyl) acrylic acid hydroxy alkyl ester etc., such as (methyl) can be enumerated
Acrylic acid 2- hydroxyl ethyl esters, (methyl) acrylic acid 2- hydroxypropyl acrylates, (methyl) acrylic acid 4- hydroxy butyl esters, (methyl) acrylic acid 6- hydroxyls oneself
Ester, (methyl) acrylic acid 8- hydroxyl monooctyl esters.
As (methyl) acrylate containing carboxyl, such as (methyl) β-acryloxypropionic acid, (methyl) third can be enumerated
Olefin(e) acid 5- carboxylic pentyl esters.
As monomer (a3), in addition to the compound represented with formula (a-3), alkene unsaturated carboxylic acid can be also enumerated.Make
It is alkene unsaturated carboxylic acid, such as (methyl) acrylic acid, butenoic acid, maleic acid, fumaric acid, itaconic acid, citraconic acid can be enumerated.
Monomer (a3) both can be used alone one kind, it is possible to use two or more.
In the mass % of polymerizable monomer 100 for forming (methyl) acrylic polymer (A), from by appropriately crosslinked
Show from the viewpoint of durability and stress relaxation properties, the consumption of monomer (a3) is preferably greater than 0 mass % and in 15 matter
Amount below %, more preferably more preferably 0.1~10 mass %, 0.2~5 mass %.
《Monomer (a4)》
(methyl) acrylic polymer (A) can also have the construction unit for coming from (a4).
As monomer (a4), can enumerate for example：The alkene esters such as vinyl acetate, propionate；Ethene, propylene, isobutyl
The olefines such as alkene；The haloalkene hydro carbons such as vinyl chloride, vinylidene chloride；The styrene monomers such as styrene, AMS；Fourth two
The diene-based monomers such as alkene, isoprene, chlorobutadiene；The nitrile monomers such as (methyl) acrylonitrile；Monomer containing amide groups.
As the monomer containing amide groups, can enumerate for example：(methyl) acrylamide, N- methyl (methyl) acrylamide,
The N- monoalkyls such as N- ethyls (methyl) acrylamide, N- propyl group (methyl) acrylamide, N- hexyls (methyl) acrylamide replace
Acrylamide；The N such as N, N- DMAA, N, N- dimethylmethacryl amides, the acryloyl of N- dialkyl group substitution
Amine.
Monomer (a4) both can be used alone one kind, it is possible to use two or more.
《The manufacturing condition of (methyl) acrylic polymer (A)》
(methyl) acrylic polymer (A) can be for example, by solution polymerization process, mass polymerization, emulsion polymerization, outstanding
Known polymerization is manufactured so far for floating polymerization etc., wherein it is preferred that solution polymerization process.Specifically, it is by polymer solvent, gathers
Conjunction property monomer loads in reaction vessel, and polymerization initiator, reacting initial temperature setting are added under the inert gas atmospheres such as nitrogen
It is usual 40~100 DEG C, preferably 50~80 DEG C, reaction system is maintained usual 50~90 DEG C, preferably 60~90 DEG C of temperature
Lower reaction 4~20 hours.
As polymerization initiator, such as azo-initiator, peroxide type polymerization initiator can be enumerated.
As azo-initiator, such as 2 can be enumerated, 2 '-azodiisobutyronitrile, 2,2 '-azo two (4- methoxyl group -2,
4- methyl pentane nitriles), 2,2 '-azo two (2- cyclopropyl propionitrile), 2,2 '-azo two (2,4- methyl pentane nitriles), 2,2 '-azo
Two (2- methylbutyronitriles), 1,1 '-azo two (hexamethylene -1- nitriles), 2- (carbamoyl azo) isobutyronitrile, 2- phenylazos -4-
Methoxyl group -2,4- methyl pentane nitriles, two acidified 2,2 '-azos two (2- amidine propanes), (N, the N methylene of '-two of 2,2 '-azo two
Base NSC 18620), 2,2 '-azo two [2- methyl-N- (2- ethoxys)-propionamide], 2,2 '-azo two (isobutyramide) two be hydrated
Thing, 4,4 '-azo two (4- cyanopentanoic acids), 2,2 '-azo two (2- cyano group propyl alcohol), dimethyl -2,2 ' (the 2- methyl of-azo two
Propionic ester), the azo-compound such as 2,2 '-azo two [2- methyl-N- (2- ethoxys) propionamide].
As peroxide type polymerization initiator, such as TBHP, cumyl hydroperoxide, peroxide can be enumerated
Change diisopropylbenzene (DIPB), benzoyl peroxide, lauroyl peroxide, peroxidating hexanoyl, di-isopropyl peroxydicarbonate, peroxidating two
The 2- Octyl Nitrites of carbonic acid two, tert-Butyl peroxypivalate, 2,2- bis- (peroxidating 4,4- di-t-butyls cyclohexyl) propane, 2,2-
Two (tert-amylcyclohexyls of peroxidating 4,4- bis-) propane, 2,2- bis- (the t-octyl cyclohexyl of peroxidating 4,4- bis-) propane, 2,2- bis-
(bis- α of peroxidating 4,4--cumyl cyclohexyl) propane, 2,2- bis- (peroxidating 4,4- di-t-butyls cyclohexyl) butane, (mistakes of 2,2- bis-
Oxidation 4,4- bis- t-octyl cyclohexyl) butane.
Polymerization initiator can be used alone one kind, it is possible to use two or more.
Also it is not limited in multiple addition polymerization initiator in polymerization.
Relative to the mass parts of polymerizable monomer 100 for forming (methyl) acrylic polymer (A), with generally 0.001
~5 mass parts, the amount preferably in the range of 0.005~3 mass parts use polymerization initiator.In addition, in above-mentioned polymerisation,
Addition polymerization initiator, chain-transferring agent, polymerizable monomer, polymer solvent can also suitably be added.
As the polymer solvent for polymerisation in solution, can enumerate for example：Benzene,toluene,xylene etc. is aromatic hydrocarbon；Positive penta
The aliphatic hydrocarbons such as alkane, n-hexane, normal heptane, normal octane；The ester ring type hydro carbons such as pentamethylene, hexamethylene, cycloheptane, cyclooctane；
Diethyl ether, diisopropyl ether, 1,2- dimethoxy-ethanes, butyl oxide, tetrahydrofuran, dioxs (dioxane), methyl phenyl ethers anisole, benzene second
The ethers such as ether, diphenyl ether；The halogenated hydrocarbons such as chloroform, carbon tetrachloride, 1,2- dichloroethanes, chlorobenzene；Ethyl acetate, propyl acetate,
The esters such as butyl acetate, methyl propionate；The ketones such as acetone, MEK, diethyl ketone, methylisobutylketone, cyclohexanone；N, N- dimethyl
The amide-types such as formamide, DMAC N,N' dimethyl acetamide, 1-METHYLPYRROLIDONE；The nitriles such as acetonitrile, benzonitrile；Dimethyl sulfoxide, ring
The sulfoxide types such as fourth sulfone.
Polymer solvent both can be used alone one kind, it is possible to use two or more.
《The physical property and content of (methyl) acrylic polymer (A)》
(methyl) acrylic polymer (A) is the Weight-average molecular determined for example, by gel permeation chromatography (GPC method)
Amount (Mw) in terms of polystyrene conversion value generally more than 400,000, be preferably 450,000~2,000,000, more preferably 600,000~1,800,000,
More preferably 800,000~1,800,000 polymer (A-1).If Mw is more than above-mentioned lower limit, in the resistance to of adhesive phase
It is long preferred on this aspect of property.It is excellent on the coating of adhesive composition this aspect if Mw is below above-mentioned higher limit
Choosing.
The molecular weight distribution (weight average molecular weight (Mw)/number-average molecular weight (Mn)) that polymer (A-1) is determined by GPC method is led to
It is often 2~60, preferably 3~45, more preferably 3~20.If Mw/Mn is more than above-mentioned lower limit, to substrate or partially
It is preferred that the piece etc. that shakes is showed on adaptation this aspect.If Mw/Mn is below above-mentioned higher limit, in excellent heat resistance and guarantor
It is preferred to hold on durability this aspect.
(methyl) acrylic polymer (A) only can be made up of above-mentioned polymer (A-1).Additionally, (methyl) acrylic acid
Compound (A) of birdsing of the same feather flock together can also be the admixture of above-mentioned polymer (A-1) and the polymer (A-2) of low-molecular-weight.If using upper
Admixture is stated, is then preferred improving wetability and improving on stress retentivity this aspect.
Relative to the mass parts of above-mentioned polymer (A-1) 100, the content of the polymer (A-2) of low-molecular-weight is preferably in 50 matter
Below amount part, more preferably below 40 mass parts, more preferably 1~30 mass parts.
The Mw that the polymer (A-2) of low-molecular-weight is determined by GPC method in terms of polystyrene conversion value generally 50,000 with
Under, preferably 1000~50,000, more preferably 2000~20,000.
The glass transition temperature (Tg) of (methyl) acrylic polymer (A) can come for example, by differential scanning calorimeter
Determine, additionally, can be calculated according to Fox formula by the monomeric unit and its content ratio that constitute the copolymer.For example, can be according to
The glass transition temperature (Tg) tried to achieve by Fox formula reaches generally -70~10 DEG C, preferably -60~0 DEG C of condition synthesizes
(methyl) acrylic polymer (A).The glass transition temperature of the homopolymers being made up of each monomer in Fox formula can be used example
Such as《Polymer handbook (Polymer Handbook)》Described number in fourth edition (Wiley-Interscience 2003)
Value.
[crosslinking agent (B)]
Adhesive composition of the invention has crosslinking agent (B).Crosslinking agent (B) is according to meeting to (methyl) acrylic
The crosslinkable groups that thing (A) is imported suitably are selected, and such as isocyanate compound, epoxide, metal-chelating can be used
Thing.
(methyl) acrylic polymer (A) is crosslinked by crosslinking agent (B), crosslinked can be thereby formed (netted poly-
Compound), obtain the adhesive phase of excellent heat resistance.
Crosslinking agent (B) both can be used alone one kind, it is possible to use two or more.
In adhesive composition of the invention, the content of crosslinking agent (B) is fitted according to (methyl) acrylic polymer (A)
Work as selection, be 0.01~25 mass parts preferably with respect to the above-mentioned mass parts of (methyl) acrylic polymer (A) 100.More preferably
, the content of crosslinking agent (B) under the occasions of the Mw more than 800,000 of (methyl) acrylic polymer (A-1) for 0.01~
3 mass parts, are 5~25 mass parts under 400,000 occasions less than 800,000 in Mw.
By blending the crosslinking agent (B) in above range under the occasion in the Mw of (A-1) more than 800,000, by adhesive group
The adhesive phase that compound is formed shows stress relaxation properties, can obtain substantially resistant to hot.And, flexibility, adaptation
It is excellent.By admixing in the Mw of (A-1) crosslinking agent (B) in above range under 400,000 occasions less than 800,000, by
The adhesive phase that adhesive composition is formed can be obtained substantially resistant to hot due to the cohesive force of adhesive phase.And, bonding
Layer oozes out or the adhesion of piercing tip, surrounding polarizer etc. is suppressed from substrate or base material, and workability is excellent.
As isocyanate compound, usually using isocyanates chemical combination of the isocyanates radix more than 2 in a molecule
Thing, isocyanates radix is preferably 2~8, more preferably 3~6 in a molecule.If isocyanates radix is within the above range,
It is then upper in (methyl) acrylic polymer (A) and the cross-linking reaction efficiency of isocyanate compound this aspect and glued in holding
It is preferred on the flexibility of mixture this aspect.
As the diisocyanate cpd that isocyanates radix in a molecule is 2, for example aliphatic two isocyanide can be enumerated
Acid esters, alicyclic diisocyanate, aromatic diisocyanates.As aliphatic vulcabond, ethylene isocyanic acid can be enumerated
Ester, tetramethylene diisocyanate, pentamethylene diisocyanate, hexamethylene diisocyanate, 2- methyl isophthalic acids, 5- pentanes two
The carbon numbers such as isocyanates, 3- methyl isophthalic acids, 5- pentane diisocyanates, 2,2,4- trimethyl -1,6- hexamethylene diisocyanates
It is 4~30 aliphatic vulcabond.As alicyclic diisocyanate, IPDI, cyclopenta can be enumerated
Diisocyanate, cyclohexyl diisocyanate, the sub- XDI of hydrogenation, HTDI, hydrogenation two
The carbon numbers such as phenylmethane diisocyanate, hydrogenation tetramethyl Asia XDI are 7~30 alicyclic diisocyanate.
As aromatic diisocyanates, such as phenylene vulcabond, toluene di-isocyanate(TDI), the sub- isocyanic acid of dimethylbenzene two can be enumerated
The carbon numbers such as ester, naphthalene diisocyanate, diphenyl ether diisocyanate, '-diphenylmethane diisocyanate, diphenylpropane diisocyanate
It is 8~30 aromatic diisocyanates
As isocyanate compound of the isocyanates radix more than 3 in a molecule, the poly- isocyanide of such as aromatics can be enumerated
Acid esters, aliphatic polymeric isocyanate, alicyclic polymeric isocyanate.Specifically, 2,4,6- triisocyanate toluene, 1,3 can be enumerated,
5- triisocyanates benzene, 4,4 ', 4 "-triphenylmethane triisocyanate.
In addition, as isocyanate compound, above-mentioned isocyanic acid of such as isocyanates radix 2 or more than 3 can be enumerated
The polymer (such as dimer or tripolymer, biuret body, isocyanuric acid ester body) of ester compounds, derivative (such as polyalcohol
With the addition reaction product of diisocyanate cpds more than two molecules), polymer.As polynary in said derivative
Alcohol, low molecular weight polyols can enumerate the alcohol more than such as ternary such as trimethylolpropane, glycerine, pentaerythrite；Macromolecule
Weight polyalcohol can enumerate such as PPG, PEPA, acrylic polyol, polybutadiene polyol, poly- isoamyl two
Alkene polyalcohol.
Such isocyanate compound can enumerate the tripolymer of such as '-diphenylmethane diisocyanate, polymethylene polyphenyl
The biuret body or isocyanuric acid ester body of base PIC, hexamethylene diisocyanate or toluene di-isocyanate(TDI), three hydroxyls
Methylpropane and toluene di-isocyanate(TDI) or product (such as toluene di-isocyanate(TDI) or Asia of sub- XDI
Three molecule addition products of XDI), the product (example of trimethylolpropane and hexamethylene diisocyanate
As hexamethylene diisocyanate three molecule addition products), polyethers PIC, polyester PIC.
In isocyanate compound, can be on this aspect good curing performance and resistance to light leakage can be put forward, preferred trimethylolpropane
With toluene di-isocyanate(TDI) or product (Japanese polyurethane Co., Ltd. (Japanese Port リ ウ レ of sub- XDI
タ Application society) manufacture CORONATE L (U ロ ネ ー ト L), the TD-75 etc. of Soken Chemical ＆ Engineering Co., Ltd.'s manufacture), hexa-methylene two
The isocyanuric acid ester body of isocyanates or toluene di-isocyanate(TDI) be (Asahi Chemical Industry Co., Ltd (industry society of Asahi Chemical Industry) manufacture
TSE-100,2050 etc. of the manufacture of Japanese polyurethane Co., Ltd.).
As epoxide, the compound with two or more epoxy radicals in molecule can be enumerated, such as second two can be enumerated
Alcohol diglycidyl ether, polyethyleneglycol diglycidylether, glycerin diglycidyl ether, T 55,1,6- oneself
Glycol diglycidyl ether, trihydroxymethylpropanyltri diglycidyl ether, diglycidylaniline, diamines diglycidyl
Amine (ジ ア ミ Application グ リ シ ジ Le ア ミ Application), N, N, N ', N '-four glycidyl group m-xylene diamine, 1,3- are double, and (N, N- bis- shrinks
Glyceryl amino methyl).As commercially available prod, such as E-5CM of Soken Chemical ＆ Engineering Co., Ltd.'s manufacture can be enumerated, comprehensive chemical strain is ground
The E-5XM of formula commercial firm manufacture.
As metallo-chelate, can enumerate such as alkoxide, acetylacetone,2,4-pentanedione, ethyl acetoacetate etc. to aluminium, iron, copper, zinc,
The compound of the polyvalent metal coordinations such as tin, titanium, nickel, antimony, magnesium, vanadium, chromium, zirconium.Specifically, aluminium isopropoxide, secondary can be enumerated
Butyric acid aluminium, acetoacetate aluminium ethide diisopropyl ester, tri ethylacetoacetate aluminium, praseodynium aluminium.
[ionic compound (C)]
Adhesive composition of the invention is by selected from N, N- pairs of (fluorine sulphonyl) imines and double (trifluoro methylsulfonyl) imines of N, N-
Anion and organic cation constitute, and the ionic compound (C) containing fusing point more than 25 DEG C.
Adhesive composition is by that containing ionic compound (C), can reduce the adhesive formed by adhesive composition
The sheet resistance value of layer, obtains the adhesive phase with antistatic performance.
Additionally, the polarizer for being pasted with described adhesive layer generally has the diaphragm for protecting polarizer mostly,
As the diaphragm, the cellulose membranes such as tri acetyl cellulose, polycarbonate membrane, poly (ether sulfone) film etc. can be enumerated, it is particularly common
Be the cellulose membranes such as tri acetyl cellulose.
Hitherto known ionic compound is mostly that the ionic compound of hydrolysis can occur with tri acetyl cellulose,
And then hardly there is hydrolysis with tri acetyl cellulose in the ionic compound (C).Due to this point, even if described
The adhesive phase containing the ionic compound (C) is attached on diaphragm, also there is no concern that described adhesive layer is in hygrothermal environment
Under can to the diaphragm produce corrosion, the polarizer with adhesive phase excellent therefore, it is possible to obtain long-term reliability.
Anion included in ionic compound (C) is selected from N, double (fluorine sulphonyl) the imines ((FSO of N-2)2N-) and N, N- pair
(trifluoro methylsulfonyl) imines ((CF3SO2)2N-)。
As the organic cation included in ionic compound (C), can enumerate for example pyridylium, piperidines sun from
Son, pyrrolidonium cation, pyrroles's cation moiety, the cation with pyrrole ring, glyoxaline cation, tetrahydropyrimidine cation,
Dihydro-pyrimidin cation, pyrazoles cation, dihydropyazolo cation (ピ ラ ゾ リ ニ ウ system カ チ オ Application), alkylammonium sun from
Son, alkyl sulfonium cation, alkylphosphines cation and their derivative.As the cation with pyrrole ring, pyrrole can be enumerated
Cough up cation, indoles cation, carbazole cation etc..As derivative, can enumerate on the ring for constituting the organic cation and have
The carbon number for having cation of one or more alkyl etc., the alkyl is usually 1~12.
Wherein, preferred alkyl ammonium cation, it is particularly more preferred with tetraalkylammonium cation that formula (c-1) is represented.
In formula (c-1), R1、R2、R3And R4It is separately alkyl.
Preferably, R1It is alkyl that carbon number is 1~18, R2~R4It is alkyl that carbon number is 1~8.From obtaining humidity resistance more
Plus from the point of view of excellent adhesive phase, it is further preferred that R1It is alkyl that carbon number is 1~14, R2~R4It is that carbon number is 1~6
Alkyl, it is further preferred that, R1It is alkyl that carbon number is 1~10, R2~R4It is alkyl that carbon number is 1~6.It is preferred that R1、R2、
R3And R4Represented alkyl is all alkyl.Additionally, being presented from (methyl) acrylic polymer (A) and ionic compound (C)
Go out from the point of view of appropriate intermiscibility, the carbon number of alkyl is advisable within the above range.By showing appropriate intermiscibility,
While showing the good antistatic performance at initial stage, it is suppressed that with time duration occur because oozing out caused by antistatic
Performance degradation is deteriorated with the adaptation of clung body.And, humidity resistance is excellent.
As the tetraalkylammonium cation represented with formula (c-1), tetramethylammonium cation, tetraethyl ammonium sun can be enumerated
Ion, tetrabutyl ammonium cation, tetrahexyl ammonium cation, trimethyldecylammonium ammonium cation, triethyl methyl ammonium cation, three fourths
Ylmethyl ammonium cation, tributyl ethyl ammonium cations, dodecyl trimethyl ammonium cation etc..
The fusing point of ionic compound (C) more than 25 DEG C, preferably at 25 DEG C less than 60 DEG C, particularly preferably at 27 DEG C
Less than 50 DEG C.Fusing point ionic compound (C) within the above range is affine with (methyl) acrylic polymer (A)
Property it is good, and can suppress for a long time take care of when ionic compound (C) oozed out from adhesive phase.Fusing point can be for example, by differential scanning warm
Measure fixed (DSC), determined in the method described in embodiment.
As ionic compound (C), specifically, preferred tributyl-methyl phosphonium ammonium double (trifluoro methylsulfonyl) imines, positive 12
Double (fluorine sulphonyl) imines of alkyl trimethyl ammonium.
From from the viewpoint of durability, the content of the ionic compound (C) in adhesive composition of the invention relative to
The mass parts of (methyl) acrylic polymer (A) 100 are typically larger than 0 mass parts and below 15 mass parts, and preferably 0.1~10
Mass parts, more preferably 0.1~8 mass parts.
[silane coupler (D)]
Adhesive composition of the invention can also contain silane coupler (D) in addition to above-claimed cpd.By using
Silane coupler (D), makes the substrate strong bonds such as adhesive phase and glass plate, helps to prevent polarizer under high humid and warm environment
It is peeling-off.
As silane coupler (D), can enumerate for example：Vinyltrimethoxy silane, VTES, 3-
Methacryloyloxypropyl methyl dimethoxysilane, 3- methacryloxypropyl trimethoxy silanes, 3- methyl-props
Alkene methyl diethoxy silane, 3- methacryloxypropyls etc. contain polymerism insatiable hunger
With the silane coupler of group；3- glycidoxypropyltrime,hoxysilanes, 3- glycidoxypropyl groups triethoxysilane,
3- glycidoxypropyls dimethoxysilane, 3- glycidoxypropyls diethoxy silane, 2- (3,4- epoxies
Cyclohexyl) silane coupler containing epoxy radicals such as ethyl trimethoxy silane；3- TSL 8330s, 3- amino
Propyl-triethoxysilicane, N- (2- amino-ethyls) -3- TSL 8330s, N- (2- amino-ethyls) -3- amino
Hydroxypropyl methyl dimethoxysilane, 3- triethoxysilyls-N- (1,3- dimethyl-butylidene) propyl group amine, N- phenyl -3-
The silane coupler containing amino such as TSL 8330；The silicon containing halogen such as 3- r-chloropropyl trimethoxyl silanes
Alkane coupling agent.
The content of the silane coupler (D) in polarizer adhesive composition of the invention is relative to (methyl) acrylic acid
The mass parts of compound (A) 100 of birdsing of the same feather flock together are usually 0~1 mass parts, more preferably preferably 0.01~1 mass parts, 0.05~0.5 matter
Amount part.
[organic solvent (E)]
Adhesive composition of the invention preferably comprises organic solvent (E) to adjust its coating.As organic molten
Agent, can enumerate《The manufacturing condition of (methyl) acrylic polymer (A)》The polymer solvent illustrated in one column.For example, will can wrap
Polymer solution containing (methyl) acrylic polymer (A) and polymer solvent mixes with crosslinking agent (B), ionic compound (C)
Carry out modulating adhesive composition.In adhesive composition of the invention, the content of organic solvent is usually 50~90 mass %, excellent
Elect 60~90 mass % as.
In addition, " solid constituent " in this specification refers to have except above-mentioned in contained composition in adhesive composition
Whole compositions beyond machine solvent (E), " solid component concentration " refers to above-mentioned solid constituent relative to the matter of adhesive composition 100
Measure the ratio of %.
[additive]
Adhesive composition of the invention can also contain not damaging in addition to mentioned component in the range of effect of the present invention
Have selected from antioxidant, light stabilizer, preventing metal corrosion agent, tackifier, plasticizer, crosslinking accelerator, surfactant, above-mentioned
(A) (methyl) acrylic polymer and agent (リ ワ ー Network drug of doing over again beyond) in one or more.
[modulation of polarizer adhesive composition]
Polarizer adhesive composition of the invention can by with known method so far to (methyl) acrylic polymer
Compound (A), crosslinking agent (B), ionic compound (C) and other compositions for using as needed are mixed to modulate.Can
It is resulting comprising (methyl) acrylic polymer (A) when enumerating for example to synthesis (methyl) acrylic polymer (A)
Polymer solution in blend crosslinking agent (B), ionic compound (C) and other compositions for using as needed.
Described adhesive composition is to the durability under the adaptation and high-temperature high-humidity of glass substrate or polarizer etc.
It is excellent, it is thus possible to suitable for fitting for polarizer and glass substrate.
[adhesive phase]
Adhesive phase of the invention is formed by above-mentioned adhesive with composition.Described adhesive layer can be above-mentioned viscous by carrying out
Cross-linking reaction in mixture composite is obtained, and specifically can make (methyl) acrylic polymer (A) by with crosslinking agent (B)
It is crosslinked to obtain.
The formation condition of adhesive phase is for example as described below.Adhesive composition of the invention is coated on supporting mass,
Temperature is different according to solvent species, but generally 50~150 DEG C, preferably carried out at 60~100 DEG C usually 1~10 minute,
The drying of preferably 2~7 minutes and remove solvent, formed film.The thickness of dry coating is usually 5~75 μm, preferably 10
~50 μm.
Adhesive phase is preferably formed under the following conditions.Adhesive composition of the invention is coated on supporting mass,
On the film formed under above-mentioned condition after stickup cover layer, at usual 5~60 DEG C, preferably 15~40 DEG C and usual 30~70%
Conserved in the environment of RH, preferably 40~70%RH usual more than 3 days, preferably 7~10 days.If in cooking conditions as described above
Under be crosslinked, then crosslinked (network polymers) can be efficiently formed.
As the coating method of adhesive composition, known method can be used, such as by spin-coating method, cutter painting method, roller
Coating, stick coating method, scraper coating, die coating method, gravure coating method form the coating drying means of specific thickness.
As supporting mass and cover layer, can enumerate for example：The polyester films such as polyethylene terephthalate (PET)；Poly- second
The plastic foil of the polyolefin films such as alkene, polypropylene, vinyl-vinyl acetate copolymer etc..
The adhesive phase formed by adhesive composition of the invention is from suppressing polarizer distortion, cohesiveness, bonding force, again
From the viewpoint of fissility, gel fraction is preferably 20~98 mass %, more preferably 30~98 mass %, further
Preferably 35~95 mass %.
Additionally, the sheet resistance value of described adhesive layer preferably existsHereinafter, more preferably existHereinafter, particularly preferablyThe electricity of sheet resistance value indication adhesive layer surface
Resistance, it is smaller that numerical value gets over small resistor, and display antistatic performance is excellent.Sheet resistance value can be surveyed by the method for embodiment record
It is fixed.
Adhesive phase of the invention is formed by with the above-mentioned adhesive composition for constituting, even if therefore than 60 DEG C/90
Excellent durability is also showed under the conditions of the damp and hot promotion of DEG C 85 DEG C RH harsher/90%RH.
[polarizer bonding sheet]
Polarizer of the invention has the adhesive phase formed with adhesive composition by above-mentioned polarizer with bonding sheet.Make
Be bonding sheet, can enumerate for example only the double-sided adhesive sheet with above-mentioned adhesive phase, with base material and be formed on base material two sides
Above-mentioned adhesive phase double-sided adhesive sheet, with base material and be formed at base material one side on above-mentioned adhesive phase one side bonding
Piece and these bonding sheets are pasted with by the viscous of the cover layer of lift-off processing on the face not contacted with base material of adhesive phase
Close piece.
As base material and cover layer, can enumerate for example：The polyester films such as polyethylene terephthalate (PET)；Polyethylene,
The plastic foil of the polyolefin films such as polypropylene, vinyl-vinyl acetate copolymer etc..
The formation condition or gel fraction of adhesive phase are identical with condition described in [adhesive phase] one column.
The thickness of adhesive phase is usually 5~75 μm, preferably 10~50 μm from from the viewpoint of maintaining bond properties.Base
The thickness of material and cover layer is not particularly limited, but usually 10~125 μm, preferably 25~75 μm.
[polarizer and layered product with adhesive phase]
Polarizer with adhesive phase of the invention have polarizer and at least one side of above-mentioned polarizer by this
The adhesive phase that invention polarizer is formed with adhesive composition.In addition, in this specification, " polarizer " is with comprising " polarizing coating "
Implication use.
As polarizer, polarizer known so far can be used, can enumerate for example has polarizer and configuration described
The polarizer of the polarizer diaphragm on the single or double of polarizer.
As polarizer, can enumerate in the film for for example making to be made up of polyvinyl alcohol resin containing after polarized component by it
Stretched film obtained from stretching.As polyvinyl alcohol resin, such as polyvinyl alcohol, polyvinyl formal, poly- second can be enumerated
Ketene acetal, EVAc it is saponified.As polarized component, such as iodine or dichroism dye can be enumerated
Material.
As polarizer diaphragm, can enumerate for example by acetyl group such as tri acetyl cellulose, diacetyl celluloses
Film, polycarbonate membrane, poly (ether sulfone) film that the celluloses such as cellulose are constituted.In the present invention, using cellulose membrane as polarizer
Diaphragm, even if under the occasion that adhesive phase connects and formed with the cellulose membrane, long-term reliability, specifically wet-heat resisting
Property is also excellent.
The thickness of polarizer is usually 30~250 μm, preferably 50~200 μm.
The method for forming adhesive phase on polarizer surface is not particularly limited, and can enumerate using direct stick coating method etc. inclined
Shake be coated with piece surface after above-mentioned adhesive composition make its dry and curing method, by polarizer bonding sheet of the invention
The adhesive phase being had is transferred to the method for curing it behind polarizer surface.Dry and cooking conditions or gel fraction etc. with
Described condition is identical in [adhesive phase] one column.
The thickness of the adhesive phase being formed on polarizer is usually 5~75 μm, preferably 10~50 μ in terms of dry film thickness
m.In addition, adhesive phase is formed at least one side of polarizer, adhesive phase can be enumerated and be only formed at polarizer one side
On form, adhesive phase be formed at form on polarizer two sides.
There is it further, it is also possible to be laminated such as antiglare layer, phase separation layer, angle of visibility on above-mentioned polarizer and improve layer etc.
The layer of its function.
The base of liquid crystal cell is arranged on by the polarizer with adhesive phase of the invention that will be obtained in the manner described above
Liquid crystal cell is manufactured in plate surface.Here liquid crystal cell has construction of the liquid crystal layer clamped by two pieces of substrates.
For example, following layered product can be manufactured, wherein, the polarizer has polarizer and configuration in the polarizer
On diaphragm, the layered product is by the polarizer, the diaphragm, by polarizer of the invention adhesive composition shape
Into adhesive phase and glass substrate be laminated in this order.
As the substrate with liquid crystal cell, such as glass plate such as alkali-free glass plate can be enumerated.The thickness of substrate preferably exists
Below 5mm, more preferably 0.05~2mm.
[embodiment]
More specific description is carried out to the present invention below based on embodiment, but the present invention is not limited to these embodiments.With
In the record of lower embodiment etc., unless otherwise instructed, " part " expression " mass parts ".
[evaluation of ionic compound]
To 2g water and 2g ionic compounds is added in polypropylene bottle, the testing liquid that concentration is 50 mass % is made.
To 0.25g (40 μm of thickness, 40mm × 120mm) tri acetyl cellulose film is put into the testing liquid, (TAC film, Konica is beautiful
The K-10 of Co., Ltd.'s (U ニ カ ミ ノ Le タ (strain)) manufacture can be reached), impregnate it.By above-mentioned polypropylene bottle in temperature
85 DEG C, stand 300 hours afterwards in the environment of humidity 85%, above-mentioned testing liquid is gathered, using high-speed liquid chromatography (strain formula
Shimadzu Seisakusho Ltd. of commercial firm manufactures) acetic acid concentration in solution is analyzed.The results are shown in table 1.
Ionic compound used in above-mentioned evaluation is as described below.Additionally, the fusing point of ionic compound is swept by showing difference
Calorimetry (DSC) is retouched to be determined with 10 DEG C per minute of programming rate between -20 DEG C~400 DEG C.
[table 1]
Table 1
As shown in table 1, in ionic compound (C3) and (C4), the acetic acid concentration in solution is high, it is thus regarded that TAC film enters
Hydrolysis is gone.And in ionic compound (C1) and (C2), the acetic acid concentration in solution is low, it is thus regarded that the hydrolysis of TAC film is entered
Row low degree.Particularly in ionic compound (C1), the acetic acid concentration in solution is almost identical with the water of reference.
[GPC]
For (methyl) acrylic polymer (A), weight is tried to achieve by gel permeation chromatography (GPC) method, with following conditions
Average molecular weight (Mw) and number-average molecular weight (Mn).
Determine device：HLC-8320GPC (TOSOH Co., Ltd (East ソ ー (strain)) is manufactured)
The composition of GPC posts：Following four pedestals (all being manufactured by TOSOH Co., Ltd)
(1) TSKgel HxL-H (guard column)
(2)TSKgel GMHxL
(3)TSKgel GMHxL
(4)TSKgel G2500HxL
Flow velocity：1.0 ml/mins
Column temperature：40℃
Sample solution concentration：1.5% (w/v) (being diluted with tetrahydrofuran)
Mobile phase solvent：Tetrahydrofuran
It is converted into polystyrene standard
[synthesis example A1]
To 90 parts of acrylic acid of addition in the reaction unit for possessing mixer, reflux cooler, thermometer and nitrogen ingress pipe
2- methoxy acrylates, 6.5 parts of n-butyl acrylates, 3 parts of acrylic acid 2- hydroxyl ethyl esters, 0.5 part of acrylamide and 100 parts of ethyl acetate
Solvent, imports nitrogen while being warming up to 80 DEG C.Then, the 2 of 0.1 part, 2 '-azodiisobutyronitrile, in nitrogen atmosphere are added
Under the polymerisation of 6 hours is carried out in 80 DEG C.After reaction terminates, it is diluted with ethyl acetate, prepared solid component concentration is
The polymer solution of 30 mass %.The Mw of resulting (methyl) acrylic polymer A1 is 7.5 for 1,000,000, Mw/Mn.
[synthesis example A2 and A3]
In addition to polymerizable monomer used in by polymerisation content described in being changed to table 2, according to
Synthesis example A1 identical modes are synthesized, and are obtained and are comprising (methyl) acrylic polymer A2 or A3 and solid component concentration
The polymer solution of 30 mass %.Result is shown in table 2.
[synthesis example A4]
To being added in the reaction unit for possessing mixer, reflux cooler, thermometer and nitrogen ingress pipe, 100 parts of toluene are molten
Liquid, imports nitrogen while being warming up to 90 DEG C.Then, using dropping funel with 2 hours 80 parts of acrylic acid 2- methoxyl groups that drip
Ethyl ester, 20 parts of n-butyl acrylates, 2 part 2,2 '-azodiisobutyronitrile adds 1 part 2,2 '-azodiisobutyronitrile, in nitrogen
The polymerisation of 6 hours is carried out in 90 DEG C under atmosphere.After reaction terminates, be diluted with ethyl acetate, be obtained comprising toluene and
The mixed solution and solid component concentration of ethyl acetate are the polymer solution of 30 mass %.Resulting (methyl) acrylic compounds
The Mw of polymer A4-2 is 2.1 for 5,000, Mw/Mn.
Then, to 100 parts include according to (methyl) acrylic polymer A4- obtained in synthesis example A1 identical modes
1 and solid component concentration be 30 mass % polymer solution in add 10 parts comprising (methyl) acrylic polymer A4-2 and
Solid component concentration is the polymer solution of 30 mass %, and prepared solid component concentration is the polymer solution of 30 mass %.
[synthesis example A5]
Except the polymerizable monomer used in polymerisation is changed into described content in table 2 and 0.15 part is mixed
2, beyond 2 '-azodiisobutyronitrile, synthesized according to synthesis example A1 identical modes, it is obtained and includes (methyl) acrylic compounds
Polymer A5 and solid component concentration are the polymer solution of 30 mass %.Result is shown in table 2.
[synthesis example A6 and A7]
Except the polymerizable monomer used in polymerisation being changed into described content in table 2 and being made and polymerism
The blended amount of the ethyl acetate that monomer is added together in addition, is synthesized for 200 parts according to synthesis example A1 identical modes, is made
The polymer solution that (methyl) acrylic polymer A6 or A7 and solid component concentration are 25 mass % must be included.Result is shown in
Table 2.
[table 2]
Table 2
[embodiment 1]
(1) regulation of adhesive composition
To (methyl) acrylic polymer solution (solid component concentration is 30 mass %), the work that are obtained in synthesis example A1
It is (B1) of crosslinking agent (B)：(solid component concentration is 75 matter to " the CORONATE L " of Nippon Polyurethane Industry Co., Ltd.'s manufacture
Amount %), as (C1) of ionic compound (C)：(n-C4H9)3(CH3)N+(CF3SO2)2N- and the letter as silane coupler (D)
" KBM-403 " of more chemical industry Co., Ltd. (SHIN-ETSU HANTOTAI's chemical industry (strain)) manufacture is mixed, and obtains adhesive composition.
The ratio of each composition is, relative to the polymer included in (methyl) acrylic polymer solution obtained in synthesis example A1
100 parts of A1, (B1) is 0.4 part, and (C1) is 2.0 parts, and (D) is 0.2 part of amount (being all above solid constituent value).
(2) making of bonding sheet
After froth breaking, with scraper under 25 DEG C of liquid temperature in the polyethylene terephthalate film (PET by lift-off processing
Film) on be coated with the adhesive composition obtained by above-mentioned (1), at 90 DEG C dry 3 minutes, form the painting that dry film thickness is 20 μm
Film.The PET film further fitted by lift-off processing on the reverse side of the sticking veneer of the above-mentioned PET film of film, 23 DEG C/50%
Stood under RH environment after being cured within 7 days, obtained with the viscous of the adhesive phase that the thickness clamped by two pieces of PET films is 20 μm
Close piece.
(3) making of the polarizer with adhesive phase
After froth breaking, with scraper under 25 DEG C of liquid temperature in the polyethylene terephthalate film (PET by lift-off processing
Film) on be coated with the adhesive composition obtained by above-mentioned (1), at 90 DEG C dry 3 minutes, obtain with dry film thickness be 20 μm
Film bonding sheet.Make sheet above and polarizer (thickness：110 μm, Rotating fields：Tri acetyl cellulose film/polyvinyl alcohol
Film/tri acetyl cellulose film) fitted in the way of above-mentioned film is connected with polarizer, under conditions of 23 DEG C/50%RH
After standing is cured for 7 days, obtain with the adhesive phase and polarizer that PET film and thickness are 20 μm with adhesive phase
Polarizer.
[embodiment 2~10, comparative example 1~3]
In addition to described content during the blending composition in embodiment 1 is changed into table 3, according to the phase of embodiment 1
Same mode obtains adhesive composition, bonding sheet and the polarizer with adhesive phase.
In addition, each material in table 3 is as follows.
Crosslinking agent (B)
B1：The trimethylolpropane adduct of toluene di-isocyanate(TDI)
(Nippon Polyurethane Industry Co., Ltd. manufactures, CORONATE L, and solid component concentration is 75 mass %)
B2：The trimethylolpropane adduct of sub- XDI
(Soken Chemical ＆ Engineering Co., Ltd. manufactures, TD-75, and solid component concentration is 75 mass %)
B3：Epoxies crosslinking agent (Soken Chemical ＆ Engineering Co., Ltd. manufactures, E-5CM, and solid component concentration is 5 mass %)
Ionic compound (C)
It is identical with the ionic compound C1~C4 used in above-mentioned [evaluation of ionic compound].
Silane coupler (D)
D：3- glycidoxypropyltrime,hoxysilanes
(Shin-Etsu Chemial Co., Ltd manufactures, KBM-403)
[evaluation]
[gel fraction]
It is placed in sample bottle from the bonding sheet collection about 0.1g adhesive phases obtained by embodiment comparative example, is added
Shaken 4 hours after 30mL ethyl acetate, the content of the sample bottle was carried out with 200 purposes stainless steel wire netting then
Filter, dry weight is determined after the drying for carrying out 2 hours to the residue on wire netting at 100 DEG C.Bonding is obtained using following formula
The gel fraction of agent.
Gel fraction (%)=(dry weight/adhesive collection weight) × 100 (%)
[sheet resistance value]
The bonding sheet obtained in embodiment comparative example is cut into the size of 100mm × 100mm, test film is made.Will
PET film is peeled off from bonding sheet, and adhesive phase is clamped with circular surface electrode and backplate.Apply 100V voltages, determine
Sheet resistance value after 60 seconds.Additionally, determining double rings electrode method (the double リ Application utilized on the basis of JIS K6911 (nineteen ninety-five)
グ Electricity Very methods) carry out, the measure of sheet resistance value used R8252 digital electrometers (Co., Ltd. ADC ((strain) エ ー デ ィ
ー シ ー) manufacture).
[measure of bonding force]
The polarizer with adhesive phase that will be obtained by embodiment comparative example is (by PET film/adhesive phase/polarizer structure
Into layered product) cut into the size of 70mm × 25mm, test film is obtained.PET film is peeled off from test film, will with laminating roll
Being bonded to thickness in the way of adhesive phase is connected with alkali glass plate by the layered product that adhesive phase/polarizer is constituted is
On the one side of the alkali glass plate of 2mm.Resulting layered product is being adjusted into 50 DEG C/5 autoclaves of atmospheric pressure holding
20 minutes.Then, placed more than 2 hours under 23 DEG C/50%RH environment, further along the alkali glass plate table relative to clung body
The peel angle in face is that 180 DEG C of direction is pullled polarizer end with the peeling rate of 300 mm/mins, determines viscous
With joint efforts (peel strength).
[endurancing]
The polarizer with adhesive phase that will be obtained by embodiment comparative example is (by PET film/adhesive phase/polarizer structure
Into layered product) cut into the size of 150mm × 250mm, test film is obtained.PET film is peeled off from test film, laminating roll is used
It is by thickness is bonded in the way of adhesive phase is connected with alkali-free glass plate by the layered product that adhesive phase/polarizer is constituted
On the one side of the alkali metal-free glass plate of 2mm.Resulting layered product is being adjusted into 50 DEG C/5 autoclaves of atmospheric pressure
Kept for 20 minutes, breadboard is obtained.It is made two pieces of identical breadboards.Under conditions of being 85 DEG C in temperature by above-mentioned breadboard
(heat resistance) or temperature are that 85 DEG C/humidity is (humidity resistance) placement 500 hours under conditions of 90%RH.With following benchmark pair
The open defects such as foaming, the cracking of above-mentioned breadboard, the stripping of adhesive phase that the autoadhesion oxidant layer of above-mentioned breadboard rises are carried out
Visually observe and evaluate.
(benchmark)
·AA：Open defect occurring area is 0%
·BB：Open defect occurring area is more than 0% and less than 3%
·CC：Open defect occurring area is 3% less than 5%
·DD：Open defect occurring area is more than 5%
[table 3]
Claims (6)
1. a kind of polarizer adhesive composition, it contains：
(A) the gathering by (methyl) acrylate (a1) with polyoxyalkylenes or alkoxyalkyl comprising more than 41 mass %
Close property monomer polymerization obtained by (methyl) acrylic polymer,
(B) crosslinking agent and
(C) anion is selected from N, double (fluorine sulphonyl) imines of N- and double (trifluoro methylsulfonyl) imines of N, N-, cation for organic sun from
Son and ionic compound of the fusing point more than 25 DEG C.
2. polarizer adhesive composition as claimed in claim 1, it is characterised in that also contain silane coupler (D).
3. polarizer adhesive composition as claimed in claim 1 or 2, it is characterised in that in ionic compound (C), have
Machine cation is the tetraalkylammonium cation represented with formula (c-1),
In formula (c-1), R1、R2、R3And R4It is separately alkyl.
4. a kind of polarizer bonding sheet, there is the polarizer any one of claims 1 to 3 to be combined with adhesive for it
The adhesive phase that thing is formed.
5. a kind of polarizer with adhesive phase, its have polarizer and at least one side of the polarizer will by right
The adhesive phase for asking the polarizer any one of 1~3 to be formed with adhesive composition.
6. a kind of layered product, it is characterised in that polarizer has the diaphragm of polarizer and configuration on the polarizer,
The layered product is as the polarizer, the diaphragm, the polarizer bonding as any one of claims 1 to 3
The adhesive phase and glass substrate that agent composition is formed are laminated in this order.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2014209833 | 2014-10-14 | ||
| JP2014-209833 | 2014-10-14 | ||
| PCT/JP2015/076160 WO2016059926A1 (en) | 2014-10-14 | 2015-09-15 | Adhesive composition for polarizing plates, adhesive sheet, polarizing plate with adhesive layer, and laminate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN106795407A true CN106795407A (en) | 2017-05-31 |
| CN106795407B CN106795407B (en) | 2019-03-01 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201580054308.7A Active CN106795407B (en) | 2014-10-14 | 2015-09-15 | Polarizing film adhesive composition, bonding sheet, polarizing film and laminated body with adhesive phase |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JP6499193B2 (en) |
| KR (1) | KR102217610B1 (en) |
| CN (1) | CN106795407B (en) |
| TW (1) | TWI688626B (en) |
| WO (1) | WO2016059926A1 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110878191A (en) * | 2018-09-04 | 2020-03-13 | 利诺士尖端材料有限公司 | Bonding sheet for display and display including the same |
| CN110997320A (en) * | 2017-08-10 | 2020-04-10 | 综研化学株式会社 | Laminate and touch panel |
| CN111630125A (en) * | 2017-11-21 | 2020-09-04 | 日东电工株式会社 | Basic ionic liquid composition and element comprising same |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6521896B2 (en) * | 2016-04-25 | 2019-05-29 | 藤森工業株式会社 | Pressure sensitive adhesive composition and antistatic surface protective film |
| JP2017200975A (en) * | 2016-05-06 | 2017-11-09 | 王子ホールディングス株式会社 | Adhesive sheet and laminate |
| KR102314549B1 (en) * | 2016-07-08 | 2021-10-19 | 닛토덴코 가부시키가이샤 | Pressure-sensitive adhesive composition, pressure-sensitive adhesive layer, optical film with pressure-sensitive adhesive layer, image display panel, and liquid crystal display device |
| KR102186080B1 (en) * | 2017-06-27 | 2020-12-03 | 주식회사 엘지화학 | Adhesive composition, protective film and polarizing plate comprising adhesive layer comprising the same and display device comprising the same |
| JP7291474B2 (en) * | 2018-12-04 | 2023-06-15 | 三星エスディアイ株式会社 | OPTICAL FILM ADHESIVE, ADHESIVE LAYER, OPTICAL MEMBER, AND IMAGE DISPLAY DEVICE |
| TWI828646B (en) * | 2018-12-26 | 2024-01-11 | 日商日東電工股份有限公司 | Adhesive compositions for optical films, adhesive layers for optical films, and optical films with adhesive layers |
| CN113227297B (en) * | 2018-12-26 | 2023-06-13 | 日东电工株式会社 | Adhesive composition for optical film, adhesive layer for optical film, and optical film with adhesive layer |
| US11267707B2 (en) | 2019-04-16 | 2022-03-08 | Honeywell International Inc | Purification of bis(fluorosulfonyl) imide |
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- 2015-09-15 WO PCT/JP2015/076160 patent/WO2016059926A1/en active Application Filing
- 2015-09-15 KR KR1020177000619A patent/KR102217610B1/en active IP Right Grant
- 2015-09-15 JP JP2016554019A patent/JP6499193B2/en active Active
- 2015-09-15 CN CN201580054308.7A patent/CN106795407B/en active Active
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Also Published As
| Publication number | Publication date |
|---|---|
| CN106795407B (en) | 2019-03-01 |
| TWI688626B (en) | 2020-03-21 |
| JPWO2016059926A1 (en) | 2017-07-27 |
| TW201617427A (en) | 2016-05-16 |
| WO2016059926A1 (en) | 2016-04-21 |
| JP6499193B2 (en) | 2019-04-10 |
| KR20170069191A (en) | 2017-06-20 |
| KR102217610B1 (en) | 2021-02-19 |
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