CN102012535A - Polarizing plate and photocurable adhesive for forming polarizing plate - Google Patents
Polarizing plate and photocurable adhesive for forming polarizing plate Download PDFInfo
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- CN102012535A CN102012535A CN2010102661759A CN201010266175A CN102012535A CN 102012535 A CN102012535 A CN 102012535A CN 2010102661759 A CN2010102661759 A CN 2010102661759A CN 201010266175 A CN201010266175 A CN 201010266175A CN 102012535 A CN102012535 A CN 102012535A
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/30—Polarising elements
- G02B5/3025—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state
- G02B5/3033—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state in the form of a thin sheet or foil, e.g. Polaroid
- G02B5/3041—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state in the form of a thin sheet or foil, e.g. Polaroid comprising multiple thin layers, e.g. multilayer stacks
- G02B5/305—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state in the form of a thin sheet or foil, e.g. Polaroid comprising multiple thin layers, e.g. multilayer stacks including organic materials, e.g. polymeric layers
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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
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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
- C09J7/00—Adhesives in the form of films or foils
- C09J7/20—Adhesives in the form of films or foils characterised by their carriers
- C09J7/22—Plastics; Metallised plastics
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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
- C09J7/00—Adhesives in the form of films or foils
- C09J7/20—Adhesives in the form of films or foils characterised by their carriers
- C09J7/29—Laminated material
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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
- C09J7/00—Adhesives in the form of films or foils
- C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
- C09J7/38—Pressure-sensitive adhesives [PSA]
- C09J7/381—Pressure-sensitive adhesives [PSA] based on macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- C09J7/385—Acrylic polymers
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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
- C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
- C09J2203/318—Applications of adhesives in processes or use of adhesives in the form of films or foils for the production of liquid crystal displays
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Polarising Elements (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Liquid Crystal (AREA)
- Adhesive Tapes (AREA)
Abstract
The present invention provides a polarizing plate, wherein two surfaces of a polyvinyl alcohol series polarizer are respectively protected by a protecting film while the two surfaces are separated from the protecting films by adhesion layers. The adhesion layers are obtained through solidifying a photo-curing adhesive which comprises the following components: (a) 60-99.8wt% of free radical polymeric compound, (c) 0.02-40wt% of cation polymeric compound which comprises cation polymeric functional groups and does not comprise (methyl)acryloyl group, (d) an optical free radical initiating agent, and (e) an optical cation polymerization initiating agent.
Description
Technical field
The present invention relates to be used for the Polarizer of liquid crystal indicator etc. and this Polarizer forms and uses Photocurable adhesive agent.
Background technology
Use among monitor, DVD player and the TV etc. at wrist-watch, mobile phone, personal portable terminating machine (PDA), notebook, computer, liquid crystal indicator is flooded with market just hastily.Liquid crystal indicator is that the polarized condition that the switch by liquid crystal causes is carried out visible apparatus, can use polarizer from its displaying principle.Special high brightness, high-contrast and the wide visual angle of in purposes such as TV, more and more requiring, and also more and more require high permeability, high degree of polarization and high colorrendering quality etc. for polarizer.
The polarizer that uses in liquid crystal display association area etc. normally will be adsorbed with iodine or dyestuff in polyvinyl alcohol (PVA) (PVA) material carries out uniaxial tension and makes.This polyethenol series polarizer shrinks because of heat or moisture, causes the reduction of polarizing properties.Here, will be that the object that the surface of polarizer is fitted with diaphragm uses as Polarizer at PVA.
As the bonding agent that is used for polarizer is sticked together diaphragm, used the aqueous solution (PVA is a bonding agent) (with reference to patent documentation 1,2) of polyvinyl alcohol resin widely in the past.
In addition, disclosing a kind of aqueous polyurethane that uses in the patent documentation 3 is the Polarizer that bonding agent forms.
Yet, along with the progress of big pictureization that particularly is the image display device of representative in recent years, Polarizer has also been improved the requirement of maximizing with TV, become important problem.
But, use in the Polarizer of aforesaid water system bonding agent, size by thermal conductance deflection tabula rasa backlight changes, the distortion that is caused by this change in size just is present in the part of picture partly, its result is that the integral body of original picture should be shown as when deceiving, seepage part light, that is, there is light leak (spot) the significantly such problem that becomes.
From above-mentioned reason, motion has the technology (with reference to patent documentation 4) of using cationically polymerizable ultraviolet hardening bonding agent to replace the water system bonding agent.
But therefore cationically polymerizable ultraviolet hardening bonding agent, in the time will growing the solidfied material coiling tubular of size, has to be easy to generate the such problem of custom of curling when keeping owing to produce dark reaction (back polymerization) in ultraviolet ray irradiation back.And the influence of humidity when cationically polymerizable ultraviolet hardening bonding agent is solidified easily has the uneven so easily problem of solid state.Here, in order to manifest the solid state of homogeneous, be not ambient humidity, and need strictly manage the water percentage that PVA is a polarizer.
Free-radical polymerised ultraviolet hardening bonding agent such problem fewer aspect on be excellent.
But liquid crystal indicator becomes and uses under various environment along with the expansion of its purposes, and is demanding environment resistant for the Polarizer that constitutes liquid crystal indicator.
For example, for the hot durability of the demanding moisture-proof of liquid crystal indicator that with the mobile phone is the mobile purposes of representative.
As mentioned above, free-radical polymerised ultraviolet hardening bonding agent is compared with cationically polymerizable curing type bonding agent, is excellent on aspect all.
But, when using free-radical polymerised ultraviolet hardening bonding agent,, reduce polarizing properties easily if be exposed to for a long time under the hygrothermal environment, have and cutting off the polarizer crossed with iodine or dye coloring takes place easily in the end color such problem that comes off.
In addition, than hygrothermal environment more under the exacting terms (for example, impregnated in 60 ℃ warm water), the color that polarizer significantly takes place comes off.
That is,, wish to have and further improved in the past that the Polarizer of the humidity resistance of Polarizer is a truth in today that the environment for use of Polarizer becomes harsher.
Further, for easy and full intensity bonding Polarizer polyvinyl alcohol (PVA) mesentery and plastic foil, again motion and with the adhesive composition (patent documentation 5) of (methyl) acrylic acid series free-radical polymerised compound and cationically polymerizable compound.But requirement further improves this technology for punch process.
Patent documentation 1: Japanese kokai publication hei 09-258023 communique
Patent documentation 2: TOHKEMY 2005-208456 communique
Patent documentation 3: TOHKEMY 2004-37841 communique
Patent documentation 4: TOHKEMY 2008-233874 communique
Patent documentation 5: TOHKEMY 2008-260879 communique
Summary of the invention
The object of the present invention is to provide a kind of Polarizer, it serves as to constitute layer with polyethenol series polarizer and diaphragm, excellence aspect the cementability of diaphragm and polarizer and punch process, and on water tolerance also excellence.
The inventor has carried out further investigation repeatedly in order to solve above-mentioned problem, it found that by Polarizer shown below can reach described target, thereby has finished the present invention.
Promptly; the present invention relates to Polarizer, it is characterized in that, it contains the polyethenol series polarizer, Photocurable adhesive agent solidifies adhesive linkage and the diaphragm that forms; its for across described adhesive linkage by the diaphragm Polarizer that the two sides of described polarizer forms that is covered respectively
Described Photocurable adhesive agent contains host, optical free radical polymerization initiator and the light cationic polymerization initiators of being made up of free-radical polymerised compound and cationically polymerizable compound,
As described free-radical polymerised compound, the formed glass temperature that contains 60～99.8 quality % in described host is the free-radical polymerised compound (a) of-80 ℃～0 ℃ homopolymer,
As described cationically polymerizable compound, in described host, contain the cationically polymerizable compound (c) that does not possess (methyl) acryloyl group of 0.02～40 quality %,
With respect to described host 100 mass parts, contain described optical free radical polymerization initiator 1～10 mass parts, described smooth cationic polymerization initiators 0.5～5 mass parts respectively.
Further, the present invention relates to Polarizer formation and use Photocurable adhesive agent, it is characterized in that, contain host, optical free radical polymerization initiator and the light cationic polymerization initiators formed by free-radical polymerised compound and cationically polymerizable compound,
As described free-radical polymerised compound, the formed glass temperature that contains 60～99.8 quality % in described host is the free-radical polymerised compound (a) of-80 ℃～0 ℃ homopolymer,
As described cationically polymerizable compound, in described host, contain the cationically polymerizable compound (c) that does not possess (methyl) acryloyl group of 0.02～40 quality %,
With respect to described host 100 mass parts, contain described optical free radical polymerization initiator 1～10 mass parts, described smooth cationic polymerization initiators 0.5～5 mass parts respectively.
Description of drawings
Fig. 1 is for showing the sectional view (synoptic diagram) of Polarizer one example of the present invention.
Fig. 2 is for showing the process flow diagram (synoptic diagram) of polarizing plate making method one example of the present invention.
Symbol description
1,5 diaphragms
2 the 1st bond layers
3 polyethenol series polarizers
4 the 2nd bond layers
1 ' diaphragm 1 and layer 2 ' the duplexer of forming by solidification compound
5 ' diaphragm 5 and layer 4 ' the duplexer of forming by solidification compound
6 active energy beams
Embodiment
Below, describe for preferred implementation of the present invention.Can provide with polyethenol series polarizer and diaphragm by the present invention is the Polarizer that constitutes layer, the Polarizer of excellence on cementability, punch process and water tolerance.
Adhesive linkage
Below, the relevant adhesive linkage (or bond layer) that constitutes Polarizer of the present invention is described.
Adhesive linkage (symbol is 2,4 among Fig. 1 and 2) is to solidify the layer that Photocurable adhesive agent forms.
Photocurable adhesive agent contains host and the polymerization initiator of being made up of photocurable compound.Host comprises free-radical polymerised composition (free-radical polymerised compound) and cationically polymerizable composition (cationically polymerizable compound).
Free-radical polymerised composition be with can form the free-radical polymerised compound (a) that glass temperature is-80 ℃～0 ℃ a homopolymer (below, be also referred to as " free-radical polymerised compound (a) " or " low Tg free-radical polymerised compound (a) ") as neccessary composition, also can further contain and to form the free-radical polymerised compound (b) that glass temperature is 60 ℃～250 ℃ a homopolymer (below, be also referred to as " free-radical polymerised compound (b) " or " high Tg free-radical polymerised compound (b) ").That is, as free-radical polymerised composition, the glass temperature that contains homopolymer is-80 ℃～0 ℃ a free-radical polymerised compound (a), and the glass temperature that at random contains homopolymer is 60 ℃～250 ℃ a free-radical polymerised compound (b).
In low Tg free-radical polymerised compound (a), compound for simple function for example can be enumerated: be (methyl) acrylic acid terminal hydroxy group Arrcostab of representative with acrylic acid 2-hydroxy methacrylate (Tg:-9 of homopolymer ℃, below identical), acrylic acid 2-hydroxy propyl ester (7 ℃), acrylic acid 4-hydroxyl butyl ester (55 ℃);
With acrylic acid 2-methoxyl ethyl ester (43 ℃), acrylic acid 3-methoxyl butyl ester (47 ℃), tridecyl acrylate (65 ℃) and methacrylic acid tridecyl ester (37 ℃) is (methyl) acrylic acid end alkyl-alkyl ester of representative;
With diethylene glycol monoethyl ether acrylate (54 ℃), ethoxy diethylene glycol acrylate (51 ℃), methoxy poly (ethylene glycol) (n=9) acrylate (71 ℃) and methoxyl tripropylene glycol acrylate (75 ℃) is end alkyl (gathering) aklylene glycol system (methyl) acrylate of representative;
Acrylic acid phenoxy ethyl (15 ℃), acrylic acid trifluoro ethyl ester (10 ℃), ω-carboxyl-polycaprolactone acrylate (46 ℃) etc.
In addition, in the low Tg free-radical polymerised compound (a), can enumerate for polyfunctional compound: polyglycol (400) diacrylate (28 ℃), polyglycol (600) diacrylate (42 ℃), triethylene glycol dimethylacrylate (5 ℃), ethoxylation (9) trimethylolpropane triacrylate (19 ℃) etc.
Photocurable adhesive agent among the present invention can make up these materials aptly and use.
Compound for the preferred simple function of low Tg free-radical polymerised compound (a).Even low Tg free-radical polymerised compound (a) if only use polyfunctional compound, has in the not preferred situation of cutting test aspect of performance described later.Here, in order to become the also good compound of this cutting test performance, when also hanging down Tg free-radical polymerised compound (a) with polyfunctional compound conduct, about in low Tg free-radical polymerised compound (a) (being 100 quality %), being controlled to be, be preferably less than about 10 quality % less than 40 quality %.
Further, when using high Tg free-radical polymerised compound described later (b), this high Tg free-radical polymerised compound (b) is preferably not multifunctional yet, and preferred simple function.In other words, when using multifunctional free-radical polymerised compound as free-radical polymerised compound ((a) or (a)+(b)), preferably its ratio in host (being 100 quality %) for about, more preferably less than about 10 quality % less than 40 quality %.
Perhaps, the ratio of simple function free-radical polymerised compound in the free-radical polymerised compound (free-radical polymerised compound (a) and the total (b) of free-radical polymerised compound of simple function (a) or simple function) is preferably more than the 60 quality %, more preferably more than the 70 quality %, more preferably more than the 90 quality %.
This free-radical polymerised compound (a) the more preferably glass temperature of homopolymer is-60 ℃～-20 ℃ a compound, and the glass temperature of further preferred homopolymer is-60 ℃～-40 ℃ a compound.
In these low Tg free-radical polymerised compounds (a), from PVA be the angle that the cementability of polarizer improves, the compound with hydroxyl of preferred (methyl) acrylic acid hydroxyalkyl acrylate etc. wherein, is preferably acrylic acid 4-hydroxyl butyl ester.On aspect the Tg that is difficult to reduce solidfied material, preferably do not use acrylic acid 2-hydroxy methacrylate and acrylic acid 2-hydroxy propyl ester even have hydroxyl yet.That is, the carbon number of the alkyl of (methyl) acrylic acid hydroxyalkyl acrylate is preferably about 4～40.
In addition, at the cohesion that improves the bond layer after solidifying, strengthen on the aspect of bonding force, preferred ω-carboxyl-polycaprolactone list (methyl) acrylate that further uses is as low Tg free-radical polymerised compound (a).Just; because the curable of ω-carboxyl-polycaprolactone list (methyl) acrylate is not fine; therefore the lamp that kind that can be by selecting radical polymerization initiator aptly or amount are selected ultraviolet lamp is aptly selected condition of cure such as exposure intensity or exposure aptly or is selected the kind of diaphragm aptly or thickness etc., assists curable.There is no particular limitation for the degree of polymerization (n) of the caprolactone of ω-carboxyl-polycaprolactone list (methyl) acrylate, still, is preferably about n=2～20.
For example, with the 100 quality % that add up to of host, the free-radical polymerised compound of 60～99.8 quality % (a) is that 10～99.8 quality %, ω-carboxyl-polycaprolactone list (methyl) acrylate are that each scope of 0～50 quality % makes up according to (methyl) acrylic acid hydroxyalkyl acrylates such as acrylic acid 4-hydroxyl butyl esters preferably.
In addition, when mixing ω-carboxyl-polycaprolactone list (methyl) acrylate, be that 10～99.7 quality %, ω-carboxyl-polycaprolactone list (methyl) acrylate are that the scope of 0.01～50 quality % is used preferably further according to (methyl) acrylic acid hydroxyalkyl acrylate.
High Tg free-radical polymerised compound (b) for any mixing, for example can enumerate: methacrylic acid dicyclopentenyloxyethyl methacrylate (Tg:180 of homopolymer ℃, below identical), trifluoroethyl methacrylate (81 ℃), metering system tert-butyl acrylate (113 ℃), Jia Jibingxisuanyizhi (65 ℃), tetrahydrofurfuryl methacrylate (68 ℃), isobornyl acrylate (85 ℃) and acryloyl morpholine (106 ℃) etc.Wherein, from stable on heating viewpoint, preferably use isobornyl acrylate and acryloyl morpholine.
This free-radical polymerised compound (b) the more preferably glass temperature of homopolymer is 60 ℃～200 ℃ a compound, and the glass temperature of further preferred homopolymer is 80 ℃～150 ℃ a compound.
Photocurable adhesive agent of the present invention can make up these materials aptly and use.
In addition, the Tg by described low Tg free-radical polymerised compound (a), formed each homopolymer of high Tg free-radical polymerised compound (b) is the value of being obtained by following operation.
Each compound of appropriate amount and initiating agent are packed in the plastic container, and irradiation ultraviolet radiation is got 10mg with the material after solidifying and use sample as measuring, and use differential scanning calorimeter (DSC) is measured with the programming rate of 10 ℃/minute or 20 ℃/minute.
The cationically polymerizable compound (c) (below be also referred to as " cationically polymerizable compound (c) ") that does not have (methyl) acryloyl group is the compound that has the functional group of cationically polymerizable and do not have (methyl) acryloyl group; for example can enumerate: 3; 4-epoxycyclohexyl methyl-3; the 4-epoxycyclohexane carboxylate; 2-(3; 4-epoxycyclohexyl-5; 5-spiral shell-3; the 4-epoxy radicals) cyclohexane--diox; two (3; 4-epoxycyclohexyl methyl) adipate; two (3; 4-epoxy radicals-6-methyl cyclohexane ylmethyl) adipate; the vinyl cyclohexene monoxide; 1,2-epoxy radicals-4-vinyl cyclohexane etc. contains the compound of the ester ring type epoxy radicals more than 1 or the compound with oxa-cyclobutyl in 1 molecule.Cationically polymerizable compound (c) is being undertaken the task of the water tolerance that improves the adhesive linkage after solidifying.
In compound, from reactive angle, preferably use 3,4-epoxycyclohexyl methyl-3,4-epoxycyclohexane carboxylate with ester ring type epoxy radicals.
Among the present invention, from the viewpoint of guaranteeing that bonding force and punch process are good, cationically polymerizable compound (c) selects not have the compound of (methyl) acryloyl group.Though can will have cationically polymerizable compound and above-mentioned (c) and the usefulness of (methyl) acryloyl group; but; the combined amount of cationically polymerizable compound in this case with (methyl) acryloyl group; in host 100 quality %; must be controlled at less than about 20 quality %, preferably be controlled at less than about 10 quality %.
Perhaps, in whole cationically polymerizable compound, the shared ratio of cationically polymerizable compound (c) that does not have (methyl) acryloyl group is preferably more than the 50 quality %, more preferably more than the 75 quality %.
It is that 60～99.8 quality %, cationically polymerizable compound (c) are 0.02～40 quality % that the host of Photocurable adhesive agent contains free-radical polymerised compound (a), preferred free-radical polymerised compound (a) is that 60～99 quality %, cationically polymerizable compound (c) are 1～40 quality %, and more preferably free-radical polymerised compound (a) is that 90～99 quality %, cationically polymerizable compound (c) are 1～10 quality %.
Low Tg free-radical polymerised compound (a) is if be less than 60 quality %, and formed adhesive linkage becomes really up to the mark, not only can not guarantee bonding force, and has worsened punch process.
And on the other hand, low Tg free-radical polymerised compound (a) is if more than 99.8 quality %, promptly, the situation that contains cationically polymerizable compound (c) hardly, the water tolerance variation of formed adhesive linkage, if Polarizer is immersed in the warm water, the color relation of PVA polarizer can come off.
When using cellulose acetate resin film such as Triafol T as diaphragm, high Tg free-radical polymerised compound (b) helps the raising of bonding force.
When using high Tg free-radical polymerised compound (b), preferred low Tg free-radical polymerised compound (a) is that 60～75 quality %, high Tg free-radical polymerised compound (b) are that 0.01～39.98 quality %, cationically polymerizable compound (c) are 0.02～24.99 quality %, and more preferably low Tg free-radical polymerised compound (a) is that 60～70 quality %, high Tg free-radical polymerised compound (b) are that 10～35 quality %, cationically polymerizable compound (c) are 5～20 quality %.
Perhaps, the Photocurable adhesive agent in the preferred embodiment is the bonding agent of following feature:
Contain as host and can form the simple function free-radical polymerised compound (a) that glass temperature is-80 ℃～0 ℃ a homopolymer: 60～99.8 quality %, can form the simple function free-radical polymerised compound (b) that glass temperature is 60 ℃～250 ℃ a homopolymer: 0～39.98 quality % and have cationically polymerizable functional group and do not have the cationically polymerizable compound (c) of (methyl) acryloyl group: 0.02～40 quality % (wherein, above-mentioned (a)～(c) add up to 100 quality %);
And contain optical free radical polymerization initiator (d): 1～10 mass parts (adding up to 100 mass parts) and light cationic polymerization initiators (e): 0.5～5 mass parts (adding up to 100 mass parts) with respect to above-mentioned (a)～(c) with respect to above-mentioned (a)～(c) as polymerization initiator.
Further preferably contain low Tg free-radical polymerised compound (a) 60～99 quality %, high Tg free-radical polymerised compound (b) 0～39 quality %, and cationically polymerizable compound (c) 1～40 quality %.
In the Photocurable adhesive agent of the present invention, except low Tg free-radical polymerised compound (a) and high Tg free-radical polymerised compound (b), can also further add other free-radical polymerised compound.Free-radical polymerised compound as other can be enumerated urethane acrylate, epoxy acrylate, polyester acrylate and polyether acrylate.But as mentioned above, free-radical polymerised compound preferably uses in the blend range that is limited.
In addition, in Photocurable adhesive agent of the present invention, can also add suitable adjuvant if desired.At the bonding force that can increase with diaphragm, and can suppress the contraction aspect of Polarizer, the preferred silane coupling agent is as adjuvant.Preferably has acryloyl group as silane coupling agent.
Photocurable adhesive agent of the present invention contains optical free radical polymerization initiator (d).
(d) has no particular limits for the optical free radical polymerization initiator, for example can enumerate gorgeous good solid (IRGACURE)-184,907,651,1700,1800,819,369,261, moral firmly-TPO (DAROCUR-TPO) (Ciba corporate system), moral is-1173 (DAROCUR-1173) (Merck ﹠ Co., Inc.'s system (Merck), Esacure-KIP 150, TZT (Japanese Waja corporate system (Japanese SiberHegner)), Kayacure BMS, Kayacure DMBI (Japanese chemical drug corporate system) etc. firmly.
Wherein, aspect the bond layer after improving photocuring transparent, the preferred DAROCUR-TPO that carried out photobleaching that uses.
With respect to total 100 mass parts of described free-radical polymerised compound (a) and (b) and cationically polymerizable compound (c), the blending ratio of optical free radical polymerization initiator (d) is 1～10 mass parts, is preferably 1～5 mass parts.
Photocurable adhesive agent of the present invention contains light cationic polymerization initiators (e).
For example can enumerate UVACURE 1590 (Daicel-Cytec system), CPI-110P sulfonium salts such as (San-Apro systems) as light cationic polymerization initiators (e), or IRGACURE 250 (Ciba corporate system), WPI-113 (with the pure medicine corporate system of light), Rp-2074 salt compounded of iodine such as (the inferior Japanese firm in sieve ground systems) etc.
With respect to total 100 mass parts of described free-radical polymerised compound (a) and (b) and cationically polymerizable compound (c), the blending ratio of light cationic polymerization initiators (e) is 0.5～10 mass parts, is preferably 0.5～5 mass parts.
With regard to Photocurable adhesive agent, except above-mentioned host and polymerization initiator, in the scope of not damaging effect of the present invention, can also contain various known adjuvants such as polymerization inhibitor, polymerization initiation auxiliary agent, ultraviolet light absorber, plastifier, colorant, antioxidant, defoamer and plastifier as required.
Polarizer
The polyethenol series polarizer (among Fig. 1,2, symbol is 3) that uses in the Polarizer of the present invention is described.
As forming polarizer, promptly becoming the polyvinyl alcohol resin of polarizer base material, can enumerate polyvinyl alcohol (PVA), ethylene-vinyl alcohol copolymer etc., but from the water tolerance aspect, optimal ethylene-ethenol copolymer.Can enumerate as polyvinyl alcohol (PVA) remainingly has the partly-hydrolysed polyvinyl alcohol (PVA) of tens of % acetates or the not fully saponified polyvinyl alcohol (PVA) of remaining acetate or the modified polyvinylalcohol that hydroxyl is modified etc., but is not defined in especially in these alcohol.Polyvinyl alcohol resin can use a kind individually, and also two or more kinds may be used.
Can enumerate RS polymkeric substance RS-110 (saponification degree=99%, the degree of polymerization=1 of (strain) Kuraray system as the object lesson of above-mentioned polyvinyl alcohol (PVA), 000), with Kuraray POVAL LM-20SO (saponification degree=40%, the degree of polymerization=2 of corporate system, 000), the Gohsenol NM-14 (saponification degree=99%, the degree of polymerization=1,400) of Japanese synthetic chemical industry (strain) system etc.Polyvinyl alcohol (PVA) for example can use base catalyst etc. that the polymkeric substance of fatty acid vinyl esters such as vinyl acetate, propionate, pivalic acid vinyl acetate is carried out saponification and get.
Above-mentioned ethylene-vinyl alcohol copolymer is the saponified of ethene and vinyl acetate copolymer, promptly, the ethane-acetic acid ethyenyl ester random copolymers is carried out saponification and obtains, from the remaining partly-hydrolysed thing that tens of moles of % acetates are arranged, to only remaining have the saponified of several moles of % acetates or not the fully saponified thing of remaining acetate comprise that all there is no particular limitation.
Polarizer can, be orientated iodine or dichromatic dye (bitintability pigment) absorption and obtain above-mentioned polyvinyl alcohol resin filming by methods such as cast-forming methods according to known method.Described polarizer also can be to carry out polarizer crosslinked or that stretch by boric acid etc.When stretching, can be before dyeing, in the dyeing or dyeing these any one stages of back carry out, there is no particular limitation as the shape of polarizer, for example can enumerate film etc.In addition, in this instructions, the term of " film " except the little object of thickness (thickness is less than 1mm), comprises that also (for example, thickness is 1～5mm) to thick sheet.There is no particular limitation for the thickness of polarizer, about for example preferred 10～40 μ m.
Diaphragm
The diaphragm (among Fig. 1,2, symbol is 1,5) that uses in the Polarizer of the present invention is described.
There is no particular limitation for diaphragm, concrete, can use as the diaphragm of present Polarizer and by the most widely used Triafol T cellulose acetate resin films such as (TAC), or the transparent resin film lower than the moisture permeability of Triafol T.
Material as the low diaphragm of the moisture permeability of constituent ratio Triafol T for example can use thermoplastic resin excellent such as the transparency, physical strength, thermal stability, dash branch and isotropy.Object lesson as such thermoplastic resin can be enumerated cyclic olefine resin and acrylic resin.
The cyclic olefine resin is as polymerized unit and the general name of the resin of polymerization with cyclic olefin.As concrete example, can enumerate the multipolymer (representative be random copolymers) of addition polymer, cyclic olefin and alpha-olefins such as ethene, propylene of open loop (being total to) polymkeric substance, the cyclic olefin of cyclic olefin, with with these graft polymer of unsaturated carboxylic acid or derivatives thereof modification, and these hydride etc., preferred norbornene resin.The norbornene resin film can be opened 2005-164632 communique, spy by the spy and open 2006-201736 communique, spy and open the known method of records such as 2008-233279 communique and obtain.
As the cyclic olefine resin, various products are arranged on the market.As concrete example, can enumerate the trade name " ZEONOR " of Japanese auspicious father-in-law (ZEON) Co., Ltd. system, the trade name " ARTON " of JSR Corp.'s system, the trade name " TOPAS " of TICONA corporate system and the trade name " Apel " of Mitsui Chemicals, Inc's system.
Acrylic resin is the resin (=multipolymer) of major component with headed by the polymethylmethacrylate with alkyl esters such as methyl methacrylate or butyl methacrylate (methyl) acrylate.According to circumstances, ooze with other resin and close and filming.The known method that the acrylic acid mesentery can be opened records such as 2002-361712 communique by the spy obtains.
As the acrylic acid mesentery, various products are arranged on the market.Can enumerate the trade name " Acryplen " of Mitsubishi Rayon Co., Ltd's system or the trade name of KANEKA corporate system " Sunduren " as concrete example.
The diaphragm that uses in the Polarizer of the present invention, 1,5 two sides can be same compositions, also can be different compositions.For example, use the cyclic olefine resin molding in 1, and use the acrylic resin film in 5, also without any problem.
Can determine the thickness of diaphragm aptly, still,, be generally about 1～500 μ m from operation, thin layer equal angles such as intensity or the property handled.Be preferably 1～300 μ m especially, more preferably 5～200 μ m.Diaphragm 1 can be identical with 5 thickness, also can be different.
In addition, when diaphragm being set, can use the diaphragm of forming by identical polymeric material, also can use the diaphragm of forming by different polymeric material etc. in its about side in the both sides of polarizer.For example, even use the situation of acrylic acid mesentery on the two sides of polarizer, the kind of acrylic acid series polymeric compounds can be different mutually, and the adjuvant of mixing also can be different mutually, without any qualification.
Polarizer of the present invention can carry out following operation and obtain.
That is, preferably make by following method: on the face of the 1st diaphragm 1 one sides, apply the 1st Photocurable adhesive agent, form the 1st curable bond layer 2 ',
On the face of the 2nd diaphragm 5 one sides, apply the 2nd Photocurable adhesive agent, form the 2nd curable bond layer 4 ',
Then, on each face of polyethenol series polarizer 3, simultaneously/or overlap the 1st curable bond layer 2 ' and the 2nd curable bond layer 4 ' in order,
From the 2nd diaphragm 5 sides irradiation active energy beam, solidify the 1st curable bond layer 2 ' and the 2nd curable bond layer 4 '.
Above-mentioned curable bond layer 2 ' and 4 ', diaphragm 1 can be identical mutually separately with 5, also can be different mutually separately.That is, curable bond layer 2 ' and curable bond layer 4 ' (in other words, the 1st Photocurable adhesive agent and the 2nd Photocurable adhesive agent) can be same compositions, also can be different the compositions.The bond layer 2 that forms can be identical mutually with 4 thickness, also can be different, and there is no particular limitation, but generally be preferably 0.1 μ m～50 μ m, more preferably 0.5 μ m～20 μ m.
Below, based on Fig. 2, each operation is described.
Operation (a)
Operation (a) is following operation: shown in Fig. 2 (a); on the one side separately of diaphragm 1 and 5; the coating adhesive layer forms uses Photocurable adhesive agent, carries out drying etc. as required, obtains having curable bond layer 2 ', 4 ' duplexer 1 ', 5 '.
There is no particular limitation as the coating process of Photocurable adhesive agent, for example can enumerate squash type (die) rubbing method, rolling method, intaglio plate rubbing method, spin-coating method etc.
Operation (b)
Operation (b) is following operation: shown in Fig. 2 (b); respectively; to have the face (in figure be above) of the duplexer 1 ' coincidence of diaphragm 1 and curable bond layer 2 ', will have the duplexer 5 ' coincidence of diaphragm 5 and curable bond layer 4 ' another face (below among the figure being) at polyethenol series polarizer 3 at polyethenol series polarizer 3.
Operation (c)
Operation (c) is following operation: shown in Fig. 2 (c), by irradiation active energy beam 6, the curable bond layer 2 ', 4 ' that is clipped between diaphragm 1,5 and the polyethenol series polarizer 3 is solidified, form bond layer 2,4.
Among the figure, though shown from the situation of diaphragm 5 sides irradiations active energy beam 6,, also can be from diaphragm 1 side irradiation active energy beam 6, also can be simultaneously from both sides, or shine active energy beam 6 in turn from both sides.
The exposure of active energy beam is not the amount that is specially limited, and still, preferred illumination wavelength is that 200～450nm, illumination are 1～500mW/cm
2Light to make exposure be 10～5000mJ/cm
2And expose.Exposure is less than 10mJ/cm
2The time, can not promote the curing of ultra-violet solidified composition, might can not bring into play desirable performance, exposure is greater than 5000mJ/cm
2The time, it is very long that irradiation time becomes, and problem is arranged on the throughput rate.As the kind of the active energy beam that shines, can enumerate visible light, ultraviolet ray, infrared ray, X ray, alpha ray, β ray, gamma-rays etc., preferred especially ultraviolet ray.Irradiation unit as light for example preferably uses high-pressure mercury-vapor lamp, Cooper-Hewitt lamp, metal halide lamp and Excimer lamp etc.
Behind the irradiation active energy beam 6, also can at room temperature carry out wearing out about 1 week.
Via operation (c), curable bond layer 2 ', 4 ' solidifies and becomes bond layer 2,4, finishes polarizer 3 and diaphragm 1 and 5 across bond layer 2, the 4 bonding Polarizers that form (with reference to (d) among Fig. 1, Fig. 2).
In addition; Polarizer of the present invention can also be made by following method: on a face of polyethenol series polarizer 3; apply Photocurable adhesive agent; form the 1st curable bond layer 2 '; cover the surface of formed the 1st curable bond layer 2 ' with the 1st diaphragm 1; then; on another face of polyethenol series polarizer 3; apply Photocurable adhesive agent; form the 2nd curable bond layer 4 ', with the surface of formed the 2nd curable bond layer 4 ' of the 2nd diaphragm 5 coverings, next; from the 2nd diaphragm 5 sides irradiation active energy beam, solidify the 1st curable bond layer 2 ' and the 2nd curable bond layer 4 '.
Polarizer is that to contain as mentioned above with polarizer, adhesive linkage and diaphragm be the plate of necessary formation, but also can contain other any formation.For example, in position arbitrarily, can contain reflection horizon, anti-reflection layer, hard conating, stain-proofing layer, anti-fog layer, adherent layer etc. as required.
Embodiment
The Production Example of (polyethenol series polarizer)
Boric acid 20 mass parts, iodine 0.2 mass parts and potassium iodide 0.5 mass parts are dissolved in the water of 480 mass parts, are modulated into dyeing liquor.In this dyeing liquor, flood PVA film (vinylon (Vinylon) film #40, Aicello corporate system) after 30 seconds, in one direction with 2 times of stretched film, drying, obtaining thickness is the PVA polarizer of 30 μ m.
Use the acrylic film that contains ultraviolet light absorber of the beautiful sun of Mitsubishi (strain) system: HBD-002 (50 μ m) is as diaphragm 1; the cycloolefin film ZEONOR film " ZF-14 " that does not contain ultraviolet light absorber (100 μ m) that uses Nippon Zeon Co., Ltd.'s system is as diaphragm 5; on its surface separately, with 300Wmin/m
2Discharge capacity, carry out corona treatment.After surface treatment in 1 hour; use the ring rod coater # 3 photopolymerizable composition shown in the coating table 1 on diaphragm 1 and 5 respectively; form curable bond layer 2 ', 4 '; the above-mentioned PVA polarizer of clamping between this curable bond layer 2 ', 4 ', obtaining by diaphragm 1/ curable bond layer 2 '/PVA is the duplexer that polarizer 3/ curable bond layer 4 '/diaphragm 5 is formed.
Fix around this duplexer with cellophane tape, diaphragm 1 and tinplate dermatotome are joined, thereby be fixed on the tinplate dermatotome.
Is 500mW/cm with UV irradiation unit (Toshiba's system, high-pressure mercury-vapor lamp) from diaphragm 5 sides irradiation maximal illumination
2, the integration light quantity is 800mJ/cm
2Ultraviolet ray, make Polarizer.The thickness of formed each bond layer is 3～4 μ m.
Except changing the photo-curable polymeric compositions as shown in Table 1 and Table 2, make Polarizer similarly to Example 1, according to method described later, estimate its performance.
Embodiment 9 and 10
Except respectively the diaphragm among the embodiment 91 being changed to the Triafol T mesentery that contains ultraviolet light absorber of Fujiphoto (strain) system: trade name " FujiTac " (80 μ m); the cycloolefin film ZEONOR film " ZF-14 " that does not contain ultraviolet light absorber (100 μ m) that diaphragm among the embodiment 10 1 is changed to Nippon Zeon Co., Ltd.'s system in addition; obtain Polarizer similarly to Example 3, carry out same evaluation.
Embodiment 11
Except diaphragm 1 being changed to the Triafol T mesentery that contains ultraviolet light absorber of Fujiphoto (strain) system: trade name " FujiTac " (80 μ m); diaphragm 5 is changed to the Triafol T mesentery that does not contain ultraviolet light absorber: trade name " TACPHAN N882GL " (80 μ m) in addition; obtain Polarizer similarly to Example 3, carry out same evaluation.
With diaphragm 1,5 similarly to Example 11, the Photocurable adhesive agent that contains high Tg free-radical polymerised compound (b) shown in the use table 1 obtains Polarizer similarly to Example 3, carries out same evaluation.
Embodiment 13
Except the cycloolefin film ZEONOR film " ZF-14 " that does not contain ultraviolet light absorber (100 μ m) that diaphragm 1,5 is become Nippon Zeon Co., Ltd.'s system, use Photocurable adhesive agent similarly to Example 12, obtain Polarizer, carry out same evaluation.
Embodiment 14 and 15
With diaphragm 1,5 similarly to Example 13; comprising polyfunctional acrylic ester (b) or having the Photocurable adhesive agent of the cationically polymerizable compound (x) of acryloyl group shown in the use table 1; obtain Polarizer similarly to Example 13, carry out same evaluation.
Comparative example 8～11
Bonding force (peel strength)
Use cutting machine that the Polarizer that obtains is cut into the size of 25mm * 150mm, as sample.(the system DF8712S of Toyo Ink Manufacturing Co., Ltd.) sticks on sample on the sheet metal by two sides adhesion adhesive tape.Between the diaphragm of sample (Polarizer) and polarizer, set in advance the beginning of peeling off, under 23 ℃, 50%RH environment, measure bonding force with peeling rate: 300mm/min.Bonding force in the table is estimated by following benchmark.
2.5 (N/25mm) above ◎
1.5 (N/25mm)～less than 2.5 (N/25mm) zero
1.0 (N/25mm)～less than 1.5 (N/25mm) △
Less than 1.0 (N/25mm) *
Cutting test (closing force test)
Between the diaphragm of the Polarizer that obtains and polarizer, put into the cutter of cutting machine, the cutter mode of entrance when advancing cutter with following benchmark evaluation.
The cutter of cutting machine is not easy to enter intermembranous ◎
When advancing the cutter of cutting machine, cutter stops zero in the place that enters intermembranous 4～5mm
That the cutter of cutting machine successfully enters is intermembranous *
Punch process
For the Polarizer of making, use the cutter of the 100mm * 100mm of Dumbbell corporate system, press from diaphragm 1 side blow.
With the state of peeling off around the Polarizer of visualization institute punching press.
Area (100cm with respect to Polarizer
2), the ratio of the area of peeling off (%) less than 1% for ◎, 1% or more and less than 2% be more than zero, 2% and less than 3% be △, peel off area and be more than 3% be *.
Warm water immersion test (water tolerance)
Use cutting machine that the Polarizer that obtains is cut into the size of 25mm * 50mm, as sample, it is flooded 24 hours and 72 hours respectively in thermostatted water (60 ℃) after, with the color of visualization sample (Polarizer) degree that comes off.
With respect to the area of Polarizer, color come off area ratio (%) less than 10% for ◎, more than 10% and less than 30% be more than zero, 30% be *.
Show evaluation result in table 1 and the table 2.About the details of the compound that uses and diaphragm on the books below table 1.
As shown in table 1, any one embodiment can be formed on polarizer excellent on cementability, punch process and the water tolerance.
It is the situation of the Photocurable adhesive agent of 90 quality % that embodiment 3 and embodiment 6 are to use the content that does not contain high Tg free-radical polymerised compound (b) and low Tg free-radical polymerised compound (a), as low Tg free-radical polymerised compound (a) except acrylic acid 4-hydroxyl butyl ester, and with the embodiment 3 of ω-carboxyl-polycaprolactone acrylate cohesion height, excellence aspect bonding force than embodiment 6.
In addition; embodiment 12 is to use the situation of the Photocurable adhesive agent that contains high Tg free-radical polymerised compound (b); compare with the embodiment 11 that does not contain high Tg free-radical polymerised compound (b); since at diaphragm for excellence aspect the cementability of three cellulose acetate membrane; therefore, excellence aspect bonding force and water tolerance.
Further, embodiment 13 compares with embodiment 12, is the situation that diaphragm uses the low cycloolefin film of moisture-penetrability, and is more excellent aspect water tolerance.
And on the other hand, use the comparative example 1 of the Photocurable adhesive agent that does not contain cationically polymerizable compound (c), even 24 hours water tolerance is also bad.
In addition, any one in the poor comparative example 2～5 and 10 of low Tg free-radical polymerised compound (a) all is possible become really up to the mark because of the adhesive linkage after solidifying, and makes bonding force diminish, and punch process is also bad.
Further; comparative example 6,7 is few for the content of low Tg free-radical polymerised compound (a); and use the free-radical polymerised compound of 3 officials energy to replace the high Tg free-radical polymerised compound of simple function (b); and use the compound with cationically polymerizable functional group and (methyl) acryloyl group to replace the situation of cationically polymerizable compound (c), bonding force is minimum.
Comparative example 8 and 9 low Tg free-radical polymerised compound (a) though content be sufficient; but it is to use the compound with cationically polymerizable functional group and (methyl) acryloyl group to replace the situation of cationically polymerizable compound (c), and bonding force is minimum.
In addition, although comparative example 4～9 bonding forces are minimum, water tolerance is good, and it is good by the shown adaptation of cutting machine test that one of its reason is considered to.
Claims (11)
1. a Polarizer is characterized in that, it is to contain polyethenol series polarizer, Photocurable adhesive agent to solidify adhesive linkage and the diaphragm that forms, and the Polarizer that formed by the diaphragm lining respectively across described adhesive linkage of the two sides of described polarizer,
Described Photocurable adhesive agent contains host, optical free radical polymerization initiator and the light cationic polymerization initiators of being made up of free-radical polymerised compound and cationically polymerizable compound,
As described free-radical polymerised compound, the formed glass temperature that contains 60～99.8 quality % in described host is the free-radical polymerised compound (a) of-80 ℃～0 ℃ homopolymer,
As described cationically polymerizable compound, in described host, contain the cationically polymerizable compound (c) that does not possess (methyl) acryloyl group of 0.02～40 quality %,
With respect to described host 100 mass parts, contain described optical free radical polymerization initiator 1～10 mass parts, described smooth cationic polymerization initiators 0.5～5 mass parts respectively.
2. Polarizer according to claim 1, wherein, described free-radical polymerised compound (a) is a simple function.
3. Polarizer according to claim 1, wherein, described Photocurable adhesive agent contain have the ester ring type epoxy radicals compound as described cationically polymerizable compound (c).
4. Polarizer according to claim 2, wherein, described Photocurable adhesive agent contains acrylic acid 4-hydroxyl butyl ester as described free-radical polymerised compound (a).
5. Polarizer according to claim 4, wherein, described Photocurable adhesive agent further contains ω-carboxyl-polycaprolactone list (methyl) acrylate as described free-radical polymerised compound (a).
6. according to claim 4 or 5 described Polarizers, wherein, in described host, contain acrylic acid 4-hydroxyl butyl ester 10～99.8 quality %, ω-carboxyl-polycaprolactone list (methyl) acrylate 0～50 quality % as described free-radical polymerised compound (a).
7. Polarizer according to claim 1, wherein, described Photocurable adhesive agent further contains can form the free-radical polymerised compound (b) that glass temperature is 60 ℃～250 ℃ a homopolymer.
8. Polarizer according to claim 1, wherein, described cationically polymerizable compound (c) shared ratio in described cationically polymerizable compound is more than the 75 quality %.
9. a Polarizer forms and uses Photocurable adhesive agent, it is characterized in that, contains host, optical free radical polymerization initiator and the light cationic polymerization initiators be made up of free-radical polymerised compound and cationically polymerizable compound,
As described free-radical polymerised compound, the formed glass temperature that contains 60～99.8 quality % in described host is the free-radical polymerised compound (a) of-80 ℃～0 ℃ homopolymer,
As described cationically polymerizable compound, in described host, contain the cationically polymerizable compound (c) that does not possess (methyl) acryloyl group of 0.02～40 quality %,
With respect to described host 100 mass parts, contain described optical free radical polymerization initiator 1～10 mass parts, described smooth cationic polymerization initiators 0.5～5 mass parts respectively.
10. Polarizer according to claim 9 forms and uses Photocurable adhesive agent, and wherein, described free-radical polymerised compound (a) is a simple function.
11. forming, Polarizer according to claim 10 uses Photocurable adhesive agent, wherein, contain acrylic acid 4-hydroxyl butyl ester 10～99.8 quality %, ω-carboxyl-polycaprolactone list (methyl) acrylate 0～50 quality % as described free-radical polymerised compound (a).
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| JP2009-204197 | 2009-09-04 | ||
| JP2009204197 | 2009-09-04 | ||
| JP2010095020A JP4561936B1 (en) | 2009-09-04 | 2010-04-16 | Polarizing plate and light curable adhesive for forming polarizing plate |
| JP2010-095020 | 2010-04-16 |
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| CN102012535A true CN102012535A (en) | 2011-04-13 |
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| JP (2) | JP4561936B1 (en) |
| KR (1) | KR101010574B1 (en) |
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| KR101622079B1 (en) | 2015-07-24 | 2016-05-19 | 삼성에스디아이 주식회사 | Adhesive composition, polarizing plate using the same, method for preparing the same and optical member comprising the same |
| JP6300128B2 (en) * | 2016-11-14 | 2018-03-28 | 大日本印刷株式会社 | Optical film manufacturing method, optical film, optical functional member including the same, and image display device |
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| JP7491457B1 (en) | 2023-11-24 | 2024-05-28 | ａｒｔｉｅｎｃｅ株式会社 | Active energy ray curable adhesive and laminate |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005508435A (en) * | 2001-11-02 | 2005-03-31 | スリーエム イノベイティブ プロパティズ カンパニー | Hybrid adhesive, article and method |
| JP2008007694A (en) * | 2006-06-30 | 2008-01-17 | Sanyo Chem Ind Ltd | Photosensitive composition for adhesive agent |
| CN101114123A (en) * | 2006-07-28 | 2008-01-30 | 富士胶片电子材料有限公司 | Photo-setting property composition and color filter using the composition |
| WO2008111584A1 (en) * | 2007-03-15 | 2008-09-18 | Sumitomo Chemical Company, Limited | Photocurable adhesive agent, polarizing plate using the photocurable adhesive agent, method for production of the polarizing plate, optical member, and liquid crystal display device |
| JP2009073896A (en) * | 2007-09-19 | 2009-04-09 | Nippon Carbide Ind Co Inc | Adhesive composition and optical film |
| JP2009075192A (en) * | 2007-09-19 | 2009-04-09 | Jsr Corp | Method for manufacturing polarizing plate |
| CN101845286A (en) * | 2009-03-06 | 2010-09-29 | 住友化学株式会社 | Photocurable adhesive agent composition, polarization plates and manufacturing process thereof, optics and liquid crystal indicator |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05117592A (en) * | 1991-10-25 | 1993-05-14 | Ricoh Co Ltd | Adhesive |
| JPH08100163A (en) * | 1994-09-29 | 1996-04-16 | Nippon Zeon Co Ltd | Epoxy resin-based adhesive composition |
| JP3825506B2 (en) * | 1996-09-02 | 2006-09-27 | Ｊｓｒ株式会社 | Liquid curable resin composition |
-
2010
- 2010-04-16 JP JP2010095020A patent/JP4561936B1/en active Active
- 2010-04-21 TW TW099112470A patent/TWI404784B/en active
- 2010-07-21 JP JP2010164200A patent/JP5459128B2/en active Active
- 2010-08-27 CN CN201010266175.9A patent/CN102012535B/en active Active
- 2010-09-02 KR KR1020100086119A patent/KR101010574B1/en active IP Right Grant
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005508435A (en) * | 2001-11-02 | 2005-03-31 | スリーエム イノベイティブ プロパティズ カンパニー | Hybrid adhesive, article and method |
| JP2008007694A (en) * | 2006-06-30 | 2008-01-17 | Sanyo Chem Ind Ltd | Photosensitive composition for adhesive agent |
| CN101114123A (en) * | 2006-07-28 | 2008-01-30 | 富士胶片电子材料有限公司 | Photo-setting property composition and color filter using the composition |
| WO2008111584A1 (en) * | 2007-03-15 | 2008-09-18 | Sumitomo Chemical Company, Limited | Photocurable adhesive agent, polarizing plate using the photocurable adhesive agent, method for production of the polarizing plate, optical member, and liquid crystal display device |
| JP2009073896A (en) * | 2007-09-19 | 2009-04-09 | Nippon Carbide Ind Co Inc | Adhesive composition and optical film |
| JP2009075192A (en) * | 2007-09-19 | 2009-04-09 | Jsr Corp | Method for manufacturing polarizing plate |
| CN101845286A (en) * | 2009-03-06 | 2010-09-29 | 住友化学株式会社 | Photocurable adhesive agent composition, polarization plates and manufacturing process thereof, optics and liquid crystal indicator |
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Also Published As
| Publication number | Publication date |
|---|---|
| CN102012535B (en) | 2014-08-13 |
| JP4561936B1 (en) | 2010-10-13 |
| TW201109404A (en) | 2011-03-16 |
| TWI404784B (en) | 2013-08-11 |
| JP2011076058A (en) | 2011-04-14 |
| JP2011076067A (en) | 2011-04-14 |
| KR101010574B1 (en) | 2011-01-25 |
| JP5459128B2 (en) | 2014-04-02 |
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