JPH09318814A - Adhesive for polarizing plate and polarizing plate - Google Patents
Adhesive for polarizing plate and polarizing plateInfo
- Publication number
- JPH09318814A JPH09318814A JP8134927A JP13492796A JPH09318814A JP H09318814 A JPH09318814 A JP H09318814A JP 8134927 A JP8134927 A JP 8134927A JP 13492796 A JP13492796 A JP 13492796A JP H09318814 A JPH09318814 A JP H09318814A
- Authority
- JP
- Japan
- Prior art keywords
- adhesive
- polarizing plate
- polyvinyl alcohol
- metal alkoxide
- alkoxide compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Landscapes
- Adhesives Or Adhesive Processes (AREA)
- Polarising Elements (AREA)
- Adhesive Tapes (AREA)
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、偏光板用接着剤に
係わり、特にポリビニルアルコール系偏光フィルムの両
面に、酢酸セルロース系フィルムを接着剤層を介して積
層してなる偏光板において、該接着剤として好適に使用
される偏光板用接着剤およびそれを使用した偏光板に関
する。TECHNICAL FIELD The present invention relates to a polarizing plate adhesive, and more particularly to a polarizing plate obtained by laminating a cellulose acetate film on both surfaces of a polyvinyl alcohol polarizing film via an adhesive layer. The present invention relates to a polarizing plate adhesive that is preferably used as an agent and a polarizing plate using the same.
【０００２】[0002]
【従来技術】近年、卓上電子計算機、電子時計、ワープ
ロ、各種表示器機等に液晶表示装置が用いられ、これに
伴い偏光板の需要も増大している。また、市場の多様化
により、特に計器類においては過酷な条件下で使用され
る場合が多く、耐熱性、耐湿性等の耐久性および高偏光
度の偏光板が要求されている。上記偏光板の代表的なも
のの一つに、一軸延伸ポリビニルアルコール系フィルム
に沃素や二色性染料を吸着固定させたものがある。この
ポリビニルアルコール系フィルムは、薄く強度も弱いた
め、両面を光学的特性のよい酢酸セルロース系フィルム
で保護されているが、ポリビニルアルコール系フィルム
自体の耐湿性が劣ることに加え、保護フィルムとしての
酢酸セルロース系フィルムの透湿性が高いため、十分な
保護機能が得られていない。かかる偏光板のフィルム相
互の接着剤として、従来からポリビニルアルコール系接
着剤が知られているが、耐水性が不十分であり、上記保
護フィルムの高透湿性により、特に高温高湿下において
各フィルムの層間剥離が発生し易いという問題があっ
た。2. Description of the Related Art In recent years, liquid crystal display devices have been used in desk-top electronic computers, electronic timepieces, word processors, various display devices, etc., and the demand for polarizing plates has increased accordingly. Further, due to the diversification of the market, it is often used under severe conditions, especially in instruments, and there is a demand for a polarizing plate having durability such as heat resistance and moisture resistance and a high polarization degree. One of the typical polarizing plates is a uniaxially stretched polyvinyl alcohol-based film in which iodine or a dichroic dye is adsorbed and fixed. Since this polyvinyl alcohol-based film is thin and weak, both surfaces are protected by a cellulose acetate-based film having good optical characteristics, but in addition to the poor moisture resistance of the polyvinyl alcohol-based film itself, acetic acid as a protective film. Since the cellulose-based film has high moisture permeability, a sufficient protective function is not obtained. As a mutual adhesive of films of such a polarizing plate, a polyvinyl alcohol-based adhesive has been conventionally known, but its water resistance is insufficient, and due to the high moisture permeability of the above-mentioned protective film, each film particularly under high temperature and high humidity. However, there is a problem that delamination is likely to occur.
【０００３】[0003]
【発明が解決しようとする課題】本発明は、偏光板用接
着剤として耐水性、耐湿熱性に優れたポリビニルアルコ
ール系接着剤およびこれを用いた偏光板を提供すること
を課題とする。SUMMARY OF THE INVENTION It is an object of the present invention to provide a polyvinyl alcohol adhesive having excellent water resistance and wet heat resistance as a polarizing plate adhesive, and a polarizing plate using the same.
【０００４】[0004]
【課題を解決するための手段】本発明者らは、上記課題
を解決するため、鋭意研究を重ねた結果、金属アルコキ
シド化合物の加水分解、縮重合反応によってポリビニル
アルコール系樹脂の架橋による耐水化を行うことによっ
て、耐水性、耐湿熱性の良好な偏光板用接着剤が得られ
ることを見出し、本発明に至ったものである。すなわ
ち、本発明は、ポリビニルアルコール系樹脂に金属アル
コキシド化合物を配合してなる偏光板用接着剤に係わ
り、キレート剤で修飾された金属アルコキシド化合物を
配合するのが好ましい。金属アルコキシド化合物として
は、チタニウムあるいはジルコニウムのアルコキシド化
合物が好適であり、またキレート剤としては、β−ジケ
トン、β−ジケトエステルおよび２価アルコールの群か
ら選ばれる少なくとも一つを使用するのが好ましい。こ
の偏光板用接着剤は、ポリビニルアルコール系偏光フィ
ルムの両面に、酢酸セルロース系フィルムを介して積層
して偏光板とするための接着剤として、特に好適なもの
である。Means for Solving the Problems The inventors of the present invention have conducted extensive studies to solve the above problems, and as a result, hydrolyzed a metal alkoxide compound and reduced water resistance by crosslinking a polyvinyl alcohol resin by a polycondensation reaction. It was found that the adhesive for polarizing plates having good water resistance and resistance to moist heat can be obtained by carrying out, and the present invention has been completed. That is, the present invention relates to a polarizing plate adhesive obtained by blending a polyvinyl alcohol resin with a metal alkoxide compound, and it is preferable to blend a metal alkoxide compound modified with a chelating agent. The metal alkoxide compound is preferably a titanium or zirconium alkoxide compound, and the chelating agent is preferably at least one selected from the group of β-diketones, β-diketoesters and dihydric alcohols. This adhesive for polarizing plates is particularly suitable as an adhesive for laminating both sides of a polyvinyl alcohol-based polarizing film via a cellulose acetate film to form a polarizing plate.
【０００５】[0005]
【発明の実施の形態】本発明に使用されるポリビニルア
ルコール系樹脂としては、水溶性のものであればよく、
通常のポリビニルアルコール（ＰＶＡ）他に、シラン変
性ＰＶＡ、エポキシ変性ＰＶＡ、カルボキシ基変性ＰＶ
Ａ、アミノ基変性ＰＶＡ、アセト酢酸変性ＰＶＡ等も使
用しうる。これらのＰＶＡ系樹脂の重合度は特に制限は
ないが、通常１００〜５０００の範囲から選ばれ、就中
５００〜３５００が好ましい。ケン化度としては、水溶
性の範囲であれば特に制限はないが、通常７０〜１００
モル％の範囲から選ばれ、９０〜１００モル％が好まし
い。BEST MODE FOR CARRYING OUT THE INVENTION The polyvinyl alcohol-based resin used in the present invention may be any water-soluble one,
Besides ordinary polyvinyl alcohol (PVA), silane-modified PVA, epoxy-modified PVA, carboxy group-modified PV
A, amino group-modified PVA, acetoacetic acid-modified PVA, etc. may also be used. The degree of polymerization of these PVA-based resins is not particularly limited, but is usually selected from the range of 100 to 5000, preferably 500 to 3500. The saponification degree is not particularly limited as long as it is in the water-soluble range, but is usually 70 to 100.
It is selected from the range of mol% and is preferably 90 to 100 mol%.
【０００６】本発明に使用される金属アルコキシド化合
物としては、一般式；Ｒ1 ｎＭ（ＯＲ2 ）ｍ−ｎ（式
中、Ｒ1 、Ｒ2 はアルキル基、Ｍは金属、ｍは金属Ｍの
原子価、ｎは０≦ｎ≦ｍ−１となる整数である）で表さ
れる各種金属のアルコキシドであるが、官能基として２
つ以上のメトキシ基、エトキシ基、プロポキシ基等のア
ルコキシ基を持つものであればよく、且つ水溶性のもの
が好ましい。上記金属Ｍとしてはアルミニウム、銅、ホ
ウ素、チタニウム、錫、ジルコニウムが用いられるが、
就中、チタニウム或いはジルコニウム系が好ましい。こ
れらの金属アルコキシド化合物の例としては、チタニウ
ムテトラエトキシド、チタニウムテトラ−ｎ−プロポキ
シド、チタニウムテトライソプロポキシド、チタニウム
テトラ−ｎ−ブトキシド等のチタニウムアルコキシド、
およびジルコニウムテトラエトキシド、ジルコニウムテ
トライソプロポキシド、ジルコニウムテトラ−ｎ−プロ
ポキシド、ジルコニウムテトラ−ｎ−ブトキシド等のジ
ルコニウムアルコキシドを挙げることができる。The metal alkoxide compound used in the present invention has a general formula: R 1 nM (OR 2 ) mn (wherein R 1 and R 2 are alkyl groups, M is a metal, and m is a metal M). Valence, n is an integer satisfying 0 ≦ n ≦ m−1) and is an alkoxide of various metals represented by 2 as a functional group.
Any one having at least one alkoxy group such as a methoxy group, an ethoxy group and a propoxy group may be used, and a water-soluble one is preferable. Aluminum, copper, boron, titanium, tin, and zirconium are used as the metal M,
Above all, titanium or zirconium is preferable. Examples of these metal alkoxide compounds include titanium alkoxides such as titanium tetraethoxide, titanium tetra-n-propoxide, titanium tetraisopropoxide and titanium tetra-n-butoxide,
And zirconium alkoxides such as zirconium tetraethoxide, zirconium tetraisopropoxide, zirconium tetra-n-propoxide and zirconium tetra-n-butoxide.
【０００７】金属アルコキシド化合物の配合量は、ポリ
ビニルアルコール系樹脂の重合度、ケン化度にもよる
が、ポリビニルアルコール系樹脂１００重量部に対して
０．１〜５０重量部、就中１〜２０重量部が好ましい。
配合量が０．１重量部以下では耐水性が発現せず、５０
重量部以上では配合系が増粘し、ゲル化する。また、金
属アルコキシド化合物をキレート修飾するためのキレー
ト剤としては、一般式；Ｒ1 −ＣＯＣＨ2 ＣＯ−Ｒ
2 （Ｒ1 、Ｒ2 はアルキル基もしくはアリール基）で表
されるアセチルアセトン、ベンゾイルアセトンのような
β−ケトン、Ｒ3 −ＣＯＣＨ2 ＣＯＯ−Ｒ4 （Ｒ3 、Ｒ
4 はアルキル基）で表されるメチルアセトアセテート、
エチルアセトアセテートのようなβ−ジケトエステル、
およびエチレングリコール、プロピレングリコールのよ
うな２価アルコール等が挙げられる。一般に金属アルコ
キシド化合物は水との反応性が高いが、キレート剤で修
飾することにより、水との反応を抑制することができ、
接着剤として使用する際の加熱により、キレート剤は解
離するよう作用する。The amount of the metal alkoxide compound blended depends on the degree of polymerization and saponification of the polyvinyl alcohol resin, but is 0.1 to 50 parts by weight, preferably 1 to 20 parts by weight, relative to 100 parts by weight of the polyvinyl alcohol resin. Parts by weight are preferred.
If the blending amount is 0.1 parts by weight or less, water resistance is not exhibited, and
If it is more than part by weight, the compounding system thickens and gels. Moreover, as a chelating agent for chelating modification of a metal alkoxide compound, a compound represented by the general formula: R 1 —COCH 2 CO—R
2 (R 1 and R 2 are alkyl groups or aryl groups) represented by acetylacetone, β-ketone such as benzoylacetone, R 3 —COCH 2 COO—R 4 (R 3 , R 2
4 is an alkyl group) represented by methyl acetoacetate,
Β-diketoesters such as ethyl acetoacetate,
And dihydric alcohols such as ethylene glycol and propylene glycol. Generally, metal alkoxide compounds have high reactivity with water, but by modifying with a chelating agent, the reaction with water can be suppressed,
The chelating agent acts so as to be dissociated by heating when used as an adhesive.
【０００８】キレート剤の金属アルコキシド化合物への
添加比率は、金属アルコキシド化合物１モルに対して
０．５〜２０モル、就中１〜１０モルが好ましい。添加
比率が０．５モル以下では、キレート修飾の効果が少な
く、水との反応の抑制が不十分であり、また２０モル以
上では溶媒として残存し、接着時に除去し難くなる。金
属アルコキシド化合物或いはキレート修飾された金属ア
ルコキシド化合物を加水分解、縮重合させる際には、無
機または有機の酸や塩基を加えてもよい。かかる無機酸
としては塩酸、硫酸、硝酸等、有機酸としては酢酸、蓚
酸等が用いられる。塩基としてはアンモニア、有機のア
ミノ化合物等が用いられる。さらに、上記の金属アルコ
キシド化合物の配合時に、分子末端にアミノ基、グリシ
ジル基、ヒドロキシル基を有するシランカップリング剤
を併用することができる。また、必要に応じて各種の消
泡剤、防腐剤、防黴剤、凍結防止剤、粘度安定剤、着色
顔料等も任意に添加することができる。The ratio of the chelating agent added to the metal alkoxide compound is preferably 0.5 to 20 mol, and more preferably 1 to 10 mol per mol of the metal alkoxide compound. If the addition ratio is 0.5 mol or less, the effect of chelate modification is small and the reaction with water is insufficiently suppressed, and if it is 20 mol or more, it remains as a solvent and is difficult to remove during adhesion. When the metal alkoxide compound or the chelate-modified metal alkoxide compound is hydrolyzed or polycondensed, an inorganic or organic acid or base may be added. Hydrochloric acid, sulfuric acid, nitric acid or the like is used as the inorganic acid, and acetic acid, oxalic acid or the like is used as the organic acid. As the base, ammonia, an organic amino compound or the like is used. Furthermore, a silane coupling agent having an amino group, a glycidyl group or a hydroxyl group at the molecular end can be used in combination when the above metal alkoxide compound is compounded. Further, if necessary, various antifoaming agents, antiseptics, antifungal agents, antifreezing agents, viscosity stabilizers, coloring pigments and the like can be optionally added.
【０００９】[0009]
【発明の効果】本発明は、ポリビニルアルコール系樹脂
を金属アルコキシド化合物の加水分解、縮重合反応によ
り架橋することによって、耐水性や耐湿熱性の良好な偏
光板用接着剤が得られ、また金属アルコキシド化合物を
キレート剤で修飾することによって、水との反応を抑制
することができ、接着剤として反応性の制御が可能であ
る。この接着剤は、ポリビニルアルコール系偏光フィル
ムの両面に酢酸セルロース系フィルムを積層するための
偏光板用接着剤として、特に好適である。INDUSTRIAL APPLICABILITY According to the present invention, a polyvinyl alcohol-based resin is crosslinked by hydrolysis and polycondensation reaction of a metal alkoxide compound to obtain a polarizing plate adhesive having good water resistance and wet heat resistance, and a metal alkoxide. By modifying the compound with a chelating agent, the reaction with water can be suppressed, and the reactivity of the adhesive can be controlled. This adhesive is particularly suitable as a polarizing plate adhesive for laminating a cellulose acetate film on both surfaces of a polyvinyl alcohol polarizing film.
【００１０】[0010]
【発明の実施の形態】本発明の実施例および比較例にお
いて、部とあるのは重量部を意味する。また耐水性試験
および接着性試験は次の方法により評価したものであ
る。 〔耐水性試験〕各接着剤溶液を８０℃で硬化させ、次に
６０℃の熱水に２時間浸漬後の固形分残渣量により耐水
性を評価した。評価の判定基準は、初期に対する残渣の
割合を表１に示した。 〔接着性試験〕各接着剤溶液を用い、ポリビニルアルコ
ール系偏光フィルム（厚さ約３０μｍ）の両面に、三酢
酸セルロースフィルム（厚さ約８０μｍ）を貼り合わ
せ、８０℃で接着剤溶液を硬化させて、寸法５０ｍｍ×
１５０ｍｍの偏光板を作製した。この偏光板を６０℃、
湿度９５％の雰囲気に５００時間放置した後の外観およ
び接着性を観察した結果を表２に示した。外観の項は、
発泡および変色の有無を示し、接着性の項は、偏光フィ
ルムとセルロースフィルムとの間の剥離状態を、目視に
より観察した結果を、次の評価基準で示した。 ○；セルロースフィルムの浮き上がり部分が周辺端部か
ら１ｍｍ以下 △；セルロースフィルムの浮き上がり部分が周辺端部か
ら１〜５ｍｍの範囲 ×；セルロースフィルムの浮き上がり部分が周辺端部か
ら５ｍｍ以上BEST MODE FOR CARRYING OUT THE INVENTION In the examples and comparative examples of the present invention, "parts" means "parts by weight". The water resistance test and the adhesion test are evaluated by the following methods. [Water Resistance Test] Each adhesive solution was cured at 80 ° C., and then water resistance was evaluated by the amount of solid content residue after immersion in hot water at 60 ° C. for 2 hours. As a criterion for evaluation, the ratio of the residue to the initial stage is shown in Table 1. [Adhesion test] Using each adhesive solution, a cellulose triacetate film (thickness: about 80 μm) was attached to both surfaces of a polyvinyl alcohol-based polarizing film (thickness: about 30 μm), and the adhesive solution was cured at 80 ° C. 50 mm x size
A 150 mm polarizing plate was prepared. This polarizing plate at 60 ° C,
Table 2 shows the results of observing the appearance and the adhesiveness after leaving it in an atmosphere of 95% humidity for 500 hours. The appearance section is
The presence or absence of foaming and discoloration was indicated, and the adhesiveness item was obtained by visually observing the peeled state between the polarizing film and the cellulose film, and the results are shown below. ◯: The lifted portion of the cellulose film is 1 mm or less from the peripheral edge. Δ: The lifted portion of the cellulose film is in the range of 1 to 5 mm from the peripheral edge. X: The lifted portion of the cellulose film is 5 mm or more from the peripheral edge.
【００１１】実施例１ 溶解槽内に、ポリビニルアルコール樹脂（重合度１７０
０、ケン化度９８．５％）１００部を所定量（１９００
部）の水に溶解して、ＰＶＡ水溶液とした。この水溶液
を攪拌しながら、チタンテトラプロポキシド／アセチル
アセトン混合液３部（前者／後者＝１／２モル比）を滴
下し、室温において１時間混合して接着剤溶液を調整し
た。この接着剤溶液の耐水性試験および接着性試験の結
果を、表１および表２に示した。Example 1 A polyvinyl alcohol resin (degree of polymerization: 170) was placed in a dissolution tank.
0, saponification degree 98.5%) 100 parts by predetermined amount (1900
Part) to dissolve in water to obtain a PVA aqueous solution. While stirring this aqueous solution, 3 parts of titanium tetrapropoxide / acetylacetone mixed solution (former / latter = 1/2 molar ratio) was added dropwise and mixed at room temperature for 1 hour to prepare an adhesive solution. The results of the water resistance test and the adhesion test of this adhesive solution are shown in Tables 1 and 2.
【００１２】実施例２ 実施例１と同様のポリビニルアルコール樹脂１００部を
含むＰＶＡ水溶液を用い、チタンテトラプロポキシド／
アセチルアセトン混合液に代えて、ジルコニウムテトラ
−ｎ−プロポキシド／アセチルアセトン混合液３部（前
者／後者＝１／２モル比）を用いる以外は、実施例と同
様の操作により接着剤溶液を調整した。この接着剤溶液
の耐水性試験および接着性試験の結果を、表１および表
２に示した。Example 2 Using the same PVA aqueous solution containing 100 parts of polyvinyl alcohol resin as in Example 1, titanium tetrapropoxide /
An adhesive solution was prepared in the same manner as in the example except that 3 parts of zirconium tetra-n-propoxide / acetylacetone mixed solution (former / latter = 1/2 molar ratio) was used instead of the acetylacetone mixed solution. The results of the water resistance test and the adhesion test of this adhesive solution are shown in Tables 1 and 2.
【００１３】実施例３ 実施例１と同様のポリビニルアルコール樹脂に代えて、
ポリビニルアルコール樹脂（重合度３５００、ケン化度
９９．７％）を使用する以外は、実施例１と同様にして
接着剤溶液を調整した。この接着剤溶液の耐水性試験お
よび接着性試験の結果を、表１および表２に示した。Example 3 Instead of the same polyvinyl alcohol resin as in Example 1,
An adhesive solution was prepared in the same manner as in Example 1 except that a polyvinyl alcohol resin (polymerization degree: 3500, saponification degree: 99.7%) was used. The results of the water resistance test and the adhesion test of this adhesive solution are shown in Tables 1 and 2.
【００１４】比較例１ 実施例１で使用したＰＶＡ水溶液を、接着剤溶液として
使用した。この接着剤溶液の耐水性試験および接着性試
験の結果を、表１および表２に示した。Comparative Example 1 The PVA aqueous solution used in Example 1 was used as an adhesive solution. The results of the water resistance test and the adhesion test of this adhesive solution are shown in Tables 1 and 2.
【表１】 [Table 1]
【表２】 [Table 2]
Claims (5)
コキシド化合物を配合してなる偏光板用接着剤。1. An adhesive for a polarizing plate, which is obtained by blending a polyvinyl alcohol resin with a metal alkoxide compound.
剤で修飾された金属アルコキシド化合物を配合してなる
偏光板用接着剤。2. An adhesive for a polarizing plate, which comprises a polyvinyl alcohol resin and a metal alkoxide compound modified with a chelating agent.
あるいはジルコニウムのアルコキシド化合物である請求
項１又は２記載の偏光板用接着剤。3. The adhesive for polarizing plates according to claim 1, wherein the metal alkoxide compound is a titanium or zirconium alkoxide compound.
トエステルおよび２価アルコールの群から選ばれる請求
項２記載の偏光板用接着剤。4. The adhesive for a polarizing plate according to claim 2, wherein the chelating agent is selected from the group of β-diketones, β-diketoesters and dihydric alcohols.
両面に、酢酸セルロース系フィルムを接着剤層を介して
積層してなる偏光板において、該接着剤として請求項１
〜４のいずれかに記載の偏光板用接着剤が使用されてい
る偏光板。5. A polarizing plate in which a cellulose acetate film is laminated on both surfaces of a polyvinyl alcohol-based polarizing film with an adhesive layer interposed therebetween, the adhesive being used as the adhesive.
A polarizing plate in which the polarizing plate adhesive according to any one of to 4 is used.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13492796A JP3812755B2 (en) | 1996-05-29 | 1996-05-29 | Polarizing plate adhesive and polarizing plate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13492796A JP3812755B2 (en) | 1996-05-29 | 1996-05-29 | Polarizing plate adhesive and polarizing plate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH09318814A true JPH09318814A (en) | 1997-12-12 |
| JP3812755B2 JP3812755B2 (en) | 2006-08-23 |
Family
ID=15139809
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13492796A Expired - Lifetime JP3812755B2 (en) | 1996-05-29 | 1996-05-29 | Polarizing plate adhesive and polarizing plate |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3812755B2 (en) |
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| WO2005063910A1 (en) * | 2003-12-26 | 2005-07-14 | Nitto Denko Corporation | Adhesive for polarizing plate, polarizing plate, method for producing same, optical film and image display |
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| JP2015057464A (en) * | 2013-08-12 | 2015-03-26 | 日本合成化学工業株式会社 | Adhesive composition, adhesive composition for polarizing plate, adhesive for polarizing plate, and polarizing plate using the same |
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- 1996-05-29 JP JP13492796A patent/JP3812755B2/en not_active Expired - Lifetime
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| JP2010008812A (en) * | 2008-06-27 | 2010-01-14 | Chiba Inst Of Technology | Moisture resistant polarization film |
| JP2015057464A (en) * | 2013-08-12 | 2015-03-26 | 日本合成化学工業株式会社 | Adhesive composition, adhesive composition for polarizing plate, adhesive for polarizing plate, and polarizing plate using the same |
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| JP3812755B2 (en) | 2006-08-23 |
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