JP3533589B2 - Pressure-sensitive adhesive composition for polarizing plate and polarizing plate - Google Patents
Pressure-sensitive adhesive composition for polarizing plate and polarizing plateInfo
- Publication number
- JP3533589B2 JP3533589B2 JP09081197A JP9081197A JP3533589B2 JP 3533589 B2 JP3533589 B2 JP 3533589B2 JP 09081197 A JP09081197 A JP 09081197A JP 9081197 A JP9081197 A JP 9081197A JP 3533589 B2 JP3533589 B2 JP 3533589B2
- Authority
- JP
- Japan
- Prior art keywords
- meth
- weight
- molecular weight
- acrylic
- polarizing plate
- 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.)
- Expired - Fee Related
Links
Classifications
-
- 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
- C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09J133/08—Homopolymers or copolymers of acrylic acid esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/30—Polarising elements
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Organic Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polarising Elements (AREA)
- Adhesive Tapes (AREA)
- Adhesives Or Adhesive Processes (AREA)
Description
【０００１】[0001]
【発明の技術分野】本発明は、液晶素子などに使用され
る偏光板を位相差板あるいは基板に貼着するための粘着
剤およびこの粘着剤からなる層を有する偏光板に関す
る。TECHNICAL FIELD The present invention relates to a pressure-sensitive adhesive for sticking a polarizing plate used for a liquid crystal element or the like to a retardation plate or a substrate, and a polarizing plate having a layer made of this pressure-sensitive adhesive.
【０００２】[0002]
【従来技術】液晶素子は、所定の方向に配向した液晶成
分が二枚の基板間に挟持された構造を有しており、この
基板の表面には偏光板や偏光板と位相差板の積層体が貼
着されている。このような液晶素子は、表示装置として
広範な分野で使用されるようになってきている。2. Description of the Related Art A liquid crystal element has a structure in which a liquid crystal component oriented in a predetermined direction is sandwiched between two substrates, and a polarizing plate or a laminate of a polarizing plate and a retardation plate is formed on the surface of this substrate. The body is attached. Such a liquid crystal element has come to be used in a wide range of fields as a display device.
【０００３】液晶素子は、装置の軽量化、薄型化に適し
ているため、近年、この液晶素子を車載用、屋外計器
用、さらにはパソコンのディスプレイや壁掛けテレビな
どの表示装置として使用されるようになってきており、
これに伴い使用環境も非常に過酷になってきている。こ
のような過酷な条件下では、偏光板の寸法変化が生じ、
この寸法変化に伴い、発泡、ハガレが生じやすくなる。
偏光板を位相差板あるいは基板に貼着するための粘着剤
は、分子量をあげたり、架橋度をあげて粘着剤層を過酷
な条件下における使用に耐えるように改良されている。Since the liquid crystal element is suitable for making the apparatus lighter and thinner, in recent years, the liquid crystal element has been used for in-vehicle equipment, outdoor instruments, and as a display device for personal computer displays, wall-mounted televisions, and the like. Is becoming
As a result, the usage environment has become extremely severe. Under such severe conditions, dimensional changes of the polarizing plate occur,
Along with this dimensional change, foaming and peeling are likely to occur.
The pressure-sensitive adhesive for adhering the polarizing plate to the retardation plate or the substrate has been improved so that the pressure-sensitive adhesive layer can be used under severe conditions by increasing the molecular weight or the degree of crosslinking.
【０００４】しかしながら、粘着剤の分子量をあげた
り、架橋度をあげて粘着剤層を過酷な条件における使用
に耐えられるようすることは、偏光板の寸法変化を粘着
剤で抑制しようとするものであり、一定の寸法変化ある
いは一定期間の寸法変化は抑えることができるが、長期
間の使用により偏光板の寸法変化によって生ずる内部応
力が偏光板周縁部に集中し、液晶素子の周縁部が中央部
より明るかったり、あるいは暗くなったりするなどの液
晶素子表面に色むらが発生する。However, increasing the molecular weight of the pressure-sensitive adhesive or increasing the degree of cross-linking so that the pressure-sensitive adhesive layer can withstand use under harsh conditions is to suppress dimensional change of the polarizing plate with the pressure-sensitive adhesive. Yes, it is possible to suppress a certain dimensional change or dimensional change for a certain period, but internal stress caused by dimensional change of the polarizing plate is concentrated on the peripheral edge of the polarizing plate due to long-term use, and the peripheral edge of the liquid crystal element is central. Color unevenness occurs on the surface of the liquid crystal element such as becoming brighter or darker.
【０００５】ところで、特開昭６０-２０７１０１号公
報には、概略、(A)反応性官能基を有するアルキル（メ
タ）アクリレート共重合体、(B)官能基を有しないアル
キル（メタ）アクリレート（共）重合体、および、(C)
上記反応性官能基と反応し得る官能基を少なくとも２個
有する多官能性化合物からなり上記(A)と(B)とを１：４
〜４：１の量比で含有する感圧接着剤層が偏光フィルム
の少なくとも一面に積層されている偏光板の発明が開示
されている。By the way, in JP-A-60-207101, roughly, (A) an alkyl (meth) acrylate copolymer having a reactive functional group, (B) an alkyl (meth) acrylate having no functional group ( (Co) polymer, and (C)
It is a polyfunctional compound having at least two functional groups capable of reacting with the above-mentioned reactive functional groups, and the above (A) and (B) are 1: 4.
The invention of a polarizing plate in which a pressure-sensitive adhesive layer, which is contained in an amount ratio of ˜4: 1, is laminated on at least one surface of a polarizing film is disclosed.
【０００６】そして、上記のような構成を採用すること
により、感圧接着剤の凝集力、接着力及び粘弾性が優れ
かつバランスがとれており、また架橋することにより遊
離の官能基が残存しなくなることから、品質が安定して
おり、高温高湿の条件下でも偏光フィルムと基板とのに
気泡が生じたりあるいは界面剥離が生じないと記載され
ている。By adopting the above-mentioned constitution, the cohesive force, adhesive force and viscoelasticity of the pressure sensitive adhesive are excellent and well balanced, and free functional groups remain by crosslinking. Since it disappears, it is described that the quality is stable and bubbles are not generated or interfacial peeling does not occur between the polarizing film and the substrate even under conditions of high temperature and high humidity.
【０００７】しかしながら、この公報に記載されている
発明において、(A)反応性官能基を有するアルキル（メ
タ）アクリレート共重合体、および、(B)官能基を有し
ないアルキル（メタ）アクリレート（共）重合体は、同
様の反応条件で製造されており、この(A)反応性官能基
を有するアルキル（メタ）アクリレート共重合体、およ
び、(B)官能基を有しないアルキル（メタ）アクリレー
ト（共）重合体はほぼ同等の分子量を有していると考え
られる。即ち、この公報には、異なる分子量を有する
(A)反応性官能基を有するアルキル（メタ）アクリレー
ト共重合体および(B)官能基を有さないアルキル（メ
タ）アクリレート（共）重合体を使用するという技術的
思想は示されていない。このため、この公報に記載され
た接着剤を使用しても、偏光板の寸法変化に対応する接
着剤層の追随性は発現しない。However, in the invention described in this publication, (A) an alkyl (meth) acrylate copolymer having a reactive functional group and (B) an alkyl (meth) acrylate (copolymer having no functional group) ) The polymer is produced under the same reaction conditions, and (A) an alkyl (meth) acrylate copolymer having a reactive functional group, and (B) an alkyl (meth) acrylate having no functional group ( The co) polymers are considered to have about the same molecular weight. That is, this publication has different molecular weights.
The technical idea of using (A) an alkyl (meth) acrylate copolymer having a reactive functional group and (B) an alkyl (meth) acrylate (co) polymer having no functional group is not shown. Therefore, even if the adhesive described in this publication is used, the adhesiveness of the adhesive layer corresponding to the dimensional change of the polarizing plate is not exhibited.
【０００８】また、特許掲載公報第２５４９３８８号に
は、「偏光板の表面に、アルキル基の炭素数が１〜１２
のアクリル酸ないしメタアクリル酸のアルキルエステル
を主成分とするアクリル系ポリマーからなる感圧性接着
剤層が設けられてなる偏光板であって、該感圧性接着剤
層が重量平均分子量１０万以下のポリマー成分を１５重
量％以下含有し、かつ重量平均分子量１００万以上のポ
リマー成分を１０重量％以上含有するアクリル系ポリマ
ーからなることを特徴とする感圧接着剤型偏光板。」の
発明が開示されている。そして、この感圧性接着剤層が
架橋されていること、架橋されてなる感圧性接着剤層中
の全ポリマー重量に対して重量平均分子量１０万以下の
未架橋ポリマー成分が１５重量％以下含有されているこ
とが開示されている。Further, Japanese Patent Publication No. 2549388 discloses that "the number of carbon atoms of an alkyl group is 1 to 12 on the surface of a polarizing plate.
Of the acrylic acid or methacrylic acid alkyl ester as a main component, which is a polarizing plate provided with a pressure-sensitive adhesive layer made of an acrylic polymer, wherein the pressure-sensitive adhesive layer has a weight average molecular weight of 100,000 or less. A pressure-sensitive adhesive type polarizing plate comprising an acrylic polymer containing 15% by weight or less of a polymer component and 10% by weight or more of a polymer component having a weight average molecular weight of 1,000,000 or more. The invention is disclosed. Further, the pressure-sensitive adhesive layer is crosslinked, and 15% by weight or less of an uncrosslinked polymer component having a weight average molecular weight of 100,000 or less is contained with respect to the total weight of the polymer in the crosslinked pressure-sensitive adhesive layer. Is disclosed.
【０００９】この公報に記載されている発明では、感圧
性接着剤層中における重量平均分子量１００万以上の高
分子量ポリマーの含有率は１０重量％以上であり、高濃
度で含有されているが、逆に重量平均分子量１０万以下
の低分子量ポリマーの含有率が１５重量％以下であり、
この発明では、低分子量ポリマーの含有率を低くしよう
としている。本発明者の検討によると、このように低分
子量ポリマーの含有率が低いと、偏光板の寸法変化に対
する感圧性接着剤層の追随性が低く、一定の範囲内で生
ずる内部応力には抗することができるが、長期間に亘っ
て繰返し生ずる内部応力が偏光板周縁部に集中し、液晶
素子の周縁部が中心部より明るくなったり、あるいは暗
くなったりするなど、液晶素子表面に色むらが発生す
る。即ち、この公報に記載されている発明では、高分子
量ポリマーを多量に使用することにより、感圧性接着剤
が長期間の使用により生ずる内部応力にも抗するように
しているのである。従って、この公報に開示されている
発明には、接着された偏光板と液晶セル基板との間に生
ずる内部応力を接着剤層で吸収して長期間の使用によっ
て生ずる内部応力を吸収して偏光板と液晶セル基板との
間の内部歪みを是正しようとする技術的思想は存在しな
い。従って、この公報に記載されている接着剤を用いて
も偏光板の寸法変化に対応した追随性を有する接着剤層
を形成することはできない。In the invention described in this publication, the content of the high molecular weight polymer having a weight average molecular weight of 1,000,000 or more in the pressure-sensitive adhesive layer is 10% by weight or more, and the content is high, but On the contrary, the content of the low molecular weight polymer having a weight average molecular weight of 100,000 or less is 15% by weight or less,
This invention seeks to lower the content of low molecular weight polymers. According to the study of the present inventor, when the content of the low molecular weight polymer is low, the followability of the pressure-sensitive adhesive layer to the dimensional change of the polarizing plate is low, and the internal stress generated within a certain range is resisted. However, the internal stress that is repeatedly generated over a long period of time is concentrated on the peripheral edge of the polarizing plate, and the peripheral edge of the liquid crystal element becomes brighter or darker than the central part. Occur. That is, in the invention described in this publication, a large amount of a high molecular weight polymer is used so that the pressure-sensitive adhesive can withstand internal stress caused by long-term use. Therefore, in the invention disclosed in this publication, the internal stress generated between the bonded polarizing plate and the liquid crystal cell substrate is absorbed by the adhesive layer, and the internal stress generated by long-term use is absorbed and polarized. There is no technical idea to correct the internal distortion between the plate and the liquid crystal cell substrate. Therefore, even if the adhesive described in this publication is used, it is not possible to form an adhesive layer having conformability to the dimensional change of the polarizing plate.
【００１０】[0010]
【発明の目的】本発明は、偏光板に生ずる寸法変化に追
随するという特性を有し、高温高湿条件下における長期
間の繰返し使用によっても、発泡することがなく、界面
剥離性が発生することがなく、従って周縁部と中央部と
の色むらの少ない液晶素子を形成することができる偏光
板用粘着剤およびこの粘着剤からなる層が少なくとも一
方の面に形成された偏光板を提供することを目的として
いる。The object of the present invention is to follow the dimensional changes that occur in a polarizing plate, and even if it is repeatedly used for a long period of time under high temperature and high humidity conditions, it does not foam and exhibits interfacial peelability. Provided is a pressure-sensitive adhesive for a polarizing plate, which is capable of forming a liquid crystal element having less color unevenness between the peripheral portion and the central portion, and a polarizing plate having a layer made of this adhesive formed on at least one surface. Is intended.
【００１１】[0011]
【発明の概要】本発明の偏光板用粘着剤は、(Ａ) (メ
タ)アクリル酸エステルから誘導される繰返し単位を主
繰返し単位とし、多官能性化合物(C)に対して反応性を
有する官能基含有モノマーから誘導される繰返し単位が
０.５〜２０重量％の量で共重合すると共に重量平均分
子量が１００万以上の高分子量(メタ)アクリル系共重合
体と、該高分子量（メタ）アクリル系共重合体１００重
量部に対して、(Ｂ) 多官能性化合物(C)に対して反応
性を有する官能基含有モノマーから誘導される繰返し単
位が０〜１０重量％の量で重合した重量平均分子量３万
以下の低分子量(メタ)アクリル系(共)重合体２０〜２０
０重量部と、(Ｃ) 上記高分子量(メタ)アクリル系共重
合体(A)および／または低分子量（メタ）アクリル系
（共）重合体(B)と結合して架橋構造を形成可能な官能
基を分子内中に少なくとも２個有する多官能性化合物
０.００５〜５重量部とからなり、該高分子量（メタ）
アクリル系共重合体(A)および低分子量（メタ）アクリ
ル系（共）重合体(B)に共重合している多官能性化合物
(C)に対して反応性を有する官能基含有モノマーから誘
導される繰返し単位が、次式で表される官能基分配率で
高分子量（メタ）アクリル系共重合体(A)および低分子
量（メタ）アクリル系（共）重合体(B)に含有されるこ
とを特徴としている。SUMMARY OF THE INVENTION The pressure-sensitive adhesive for polarizing plate of the present invention has a repeating unit derived from (A) (meth) acrylic acid ester as a main repeating unit and has reactivity with a polyfunctional compound (C). A repeating unit derived from a functional group-containing monomer is copolymerized in an amount of 0.5 to 20% by weight, and a high molecular weight (meth) acrylic copolymer having a weight average molecular weight of 1,000,000 or more is used. ) The repeating unit derived from the functional group-containing monomer (B) having reactivity with the polyfunctional compound (C) is polymerized in an amount of 0 to 10% by weight based on 100 parts by weight of the acrylic copolymer. 20 to 20 low molecular weight (meth) acrylic (co) polymers having a weight average molecular weight of 30,000 or less
It is possible to form a crosslinked structure by combining with 0 part by weight of (C) the high molecular weight (meth) acrylic copolymer (A) and / or the low molecular weight (meth) acrylic (co) polymer (B). The high molecular weight (meth) compound comprises 0.005 to 5 parts by weight of a polyfunctional compound having at least two functional groups in the molecule.
Polyfunctional compound copolymerized with acrylic copolymer (A) and low molecular weight (meth) acrylic (co) polymer (B)
The repeating unit derived from a functional group-containing monomer having reactivity with (C) has a functional group partition ratio represented by the following formula: a high molecular weight (meth) acrylic copolymer (A) and a low molecular weight ( It is characterized in that it is contained in the (meth) acrylic (co) polymer (B).
【００１２】官能基分配率 ＝［低分子量(メタ)アクリ
ル系共重合体中における多官能性化合物(C)に対して反
応性を有する官能基含有モノマーから誘導される繰返し
単位のモノマー換算重量／高分子量(メタ)アクリル系共
重合体中における多官能性化合物(C)に対して反応性を
有する官能基含有モノマーから誘導される繰返し単位の
モノマー換算重量］×１００＝０〜１５重量％。Functional group distribution ratio = [weight equivalent of repeating units derived from a functional group-containing monomer having reactivity with the polyfunctional compound (C) in the low molecular weight (meth) acrylic copolymer / converted monomer weight / Monomer equivalent weight of repeating units derived from a functional group-containing monomer having reactivity with the polyfunctional compound (C) in the high molecular weight (meth) acrylic copolymer] × 100 = 0 to 15% by weight.
【００１３】また、本発明の偏光板は、(Ａ) (メタ)ア
クリル酸エステルから誘導される繰返し単位を主繰返し
単位とし、多官能性化合物(C)に対して反応性を有する
官能基含有モノマーから誘導される繰返し単位が０.５
〜２０重量％の量で共重合すると共に重量平均分子量が
１００万以上の高分子量(メタ)アクリル系共重合体と、
該高分子量（メタ）アクリル系共重合体１００重量部に
対して、(Ｂ) 多官能性化合物(C)に対して反応性を有
する官能基含有モノマーから誘導される繰返し単位が０
〜１０重量％の量で重合した重量平均分子量３万以下の
低分子量(メタ)アクリル系(共)重合体２０〜２００重量
部と、(Ｃ) 上記高分子量(メタ)アクリル系共重合体
(A)および／または低分子量（メタ）アクリル系（共）
重合体(B)と結合して架橋構造を形成可能な官能基を分
子内中に少なくとも２個有する多官能性化合物０.００
５〜５重量部とからなり、該高分子量（メタ）アクリル
系共重合体(A)および低分子量（メタ）アクリル系
（共）重合体(B)に共重合している多官能性化合物(C)に
対して反応性を有する官能基含有モノマーから誘導され
る繰返し単位が、上記式で表される官能基分配率で高分
子量（メタ）アクリル系共重合体(A)および低分子量
（メタ）アクリル系（共）重合体(B)に含有されること
を特徴とする粘着剤からなる粘着剤層が、偏光板の少な
くとも一方の面に形成されていることを特徴としてい
る。Further, the polarizing plate of the present invention comprises a repeating unit derived from (A) (meth) acrylic acid ester as a main repeating unit and contains a functional group having reactivity with the polyfunctional compound (C). 0.5 repeating units derived from monomers
A high molecular weight (meth) acrylic copolymer having a weight average molecular weight of 1,000,000 or more,
Based on 100 parts by weight of the high molecular weight (meth) acrylic copolymer, the repeating unit derived from the functional group-containing monomer (B) having reactivity with the polyfunctional compound (C) is 0.
20 to 200 parts by weight of a low molecular weight (meth) acrylic (co) polymer having a weight average molecular weight of 30,000 or less polymerized in an amount of 10 to 10% by weight, and (C) the high molecular weight (meth) acrylic copolymer
(A) and / or low molecular weight (meth) acrylic (co)
A polyfunctional compound having at least two functional groups capable of forming a crosslinked structure by binding to the polymer (B) in the molecule 0.00
5 to 5 parts by weight, which is a polyfunctional compound copolymerized with the high molecular weight (meth) acrylic copolymer (A) and the low molecular weight (meth) acrylic (co) polymer (B) ( The repeating unit derived from a functional group-containing monomer having reactivity with C) has a functional group distribution ratio represented by the above formula and has a high molecular weight (meth) acrylic copolymer (A) and a low molecular weight (meth). ) A pressure-sensitive adhesive layer made of a pressure-sensitive adhesive contained in the acrylic (co) polymer (B) is formed on at least one surface of the polarizing plate.
【００１４】本発明の偏光板用粘着剤では、多官能性化
合物と反応する（メタ）アクリル系共重合体として、重
量平均分子量が１００万以上である高分子量（メタ）ア
クリル系共重合体を使用すると共に、多官能性化合物と
の反応性がないあるいは少ない（メタ）アクリル系
（共）重合体として、重量平均分子量３万以下の低分子
量（メタ）アクリル系（共）重合体の２種類の異なる
（メタ）アクリル系重合体を使用し、かつ多官能性化合
物に対して、反応性を有する官能基の量が、高分子量
（メタ）アクリル系共重合体に比べ低分子量（メタ）ア
クリル（共）重合体の方が少ないため、低分子量体（メ
タ）アクリル系共重合体は、多官能化合物と結合するこ
とはないか、あるいは結合しても三次元架橋構造を形成
しにくい。従って、本発明の組成の粘着剤を使用するこ
とにより、高分子量（メタ）アクリル系共重合体と多官
能性化合物によって三次元架橋構造が形成され、この三
次元架橋構造中に低分子量（メタ）アクリル系（共）重
合体が存在するようになる。In the pressure-sensitive adhesive for polarizing plate of the present invention, a high molecular weight (meth) acrylic copolymer having a weight average molecular weight of 1,000,000 or more is used as the (meth) acrylic copolymer which reacts with the polyfunctional compound. Two types of low molecular weight (meth) acrylic (co) polymers with a weight average molecular weight of 30,000 or less are used as (meth) acrylic (co) polymers that have no or little reactivity with polyfunctional compounds. Of different (meth) acrylic polymers, and the amount of functional groups reactive with polyfunctional compounds is lower than that of high molecular weight (meth) acrylic copolymers. Since the amount of the (co) polymer is less, the low molecular weight (meth) acrylic copolymer does not bond with the polyfunctional compound or does not easily form a three-dimensional crosslinked structure even when bonded. Therefore, by using the pressure-sensitive adhesive of the composition of the present invention, a three-dimensional crosslinked structure is formed by the high molecular weight (meth) acrylic copolymer and the polyfunctional compound, and a low molecular weight (meth) is formed in the three-dimensional crosslinked structure. ) An acrylic (co) polymer becomes present.
【００１５】このような構成を有する本発明の偏光板用
粘着剤においては、高温高湿条件下おいて発生する発泡
やハガレを形成された三次元構造によって防止し、偏光
板の寸法変化に伴う内部応力を三次元架橋構造中に存在
する低分子量（メタ）アクリル系（共）重合体によって
吸収して、温度あるいは湿度の変化に伴う偏光板の形態
変化に追従して変化するという特性を粘着剤層に付与し
ているのである。In the pressure-sensitive adhesive for polarizing plate of the present invention having such a constitution, foaming and peeling which occur under high temperature and high humidity conditions are prevented by the formed three-dimensional structure, which is accompanied by dimensional change of the polarizing plate. The internal stress is absorbed by the low molecular weight (meth) acrylic (co) polymer existing in the three-dimensional cross-linking structure, and changes according to the shape change of the polarizing plate due to the change of temperature or humidity. It is applied to the agent layer.
【００１６】従って、この粘着剤で基板あるいは位相差
板に接着された偏光フィルムは、温度の変化、湿度の変
化などによって生ずる内部応力がこの粘着剤層によって
吸収されるので、液晶素子の周縁部が中央部より明るか
ったり、あるいは暗かったりするなどの色むらが発生せ
ず、しかも発泡、ハガレも生じない。Therefore, in the polarizing film adhered to the substrate or the retardation plate with this adhesive, internal stress caused by temperature change, humidity change, etc. is absorbed by the adhesive layer, and therefore, the peripheral portion of the liquid crystal element is absorbed. There is no unevenness in color such as lighter or darker than the center, and neither foaming nor peeling occurs.
【００１７】[0017]
【発明の具体的説明】次に本発明の偏光板用粘着剤およ
びこの粘着剤からなる粘着層を有する偏光板について具
体的に説明する。DETAILED DESCRIPTION OF THE INVENTION Next, the pressure-sensitive adhesive for polarizing plate of the present invention and the polarizing plate having a pressure-sensitive adhesive layer made of this pressure-sensitive adhesive will be specifically described.
【００１８】本発明の偏光板用粘着剤は、高分子量（メ
タ）アクリル系共重合体と、低分子量体（メタ）アクリ
ル系（共）重合体と、多官能性化合物とを含有してい
る。高分子量（メタ）アクリル系共重合体は、（メタ）
アクリル酸エステルを主成分とし、この（メタ）アクリ
ル酸エステルと多官能性化合物(C)に対して反応性を有
する官能基含有モノマーとの共重合体である。この高分
子量（メタ）アクリル系共重合体を形成する（メタ）ア
クリル酸エステルとしては、メチル（メタ）アクリレー
ト、エチル（メタ）アクリレート、プロピル（メタ）ア
クリレート、n-ブチル（メタ）アクリレート、iso-ブチ
ル（メタ）アクリレート、2-エチルヘキシル（メタ）ア
クリレート、n-オクチル（メタ）アクリレート、iso-オ
クチル（メタ）アクリレート、ラウリル（メタ）アクリ
レート、ステアリル（メタ）アクリレート、シクロヘキ
シル（メタ）アクリレート、ベンジル（メタ）アクリレ
ート、メトキシエチル（メタ）アクリレート、エトキシ
メチル（メタ）アクリレートおよびフェノキシエチル
（メタ）アクリレートなどを挙げることができる。これ
らは単独であるいは組み合わせて使用することができ
る。The pressure-sensitive adhesive for polarizing plate of the present invention contains a high molecular weight (meth) acrylic copolymer, a low molecular weight (meth) acrylic (co) polymer, and a polyfunctional compound. . The high molecular weight (meth) acrylic copolymer is (meth)
It is a copolymer of an acrylic acid ester as a main component, and this (meth) acrylic acid ester and a functional group-containing monomer having reactivity with the polyfunctional compound (C). Examples of the (meth) acrylic acid ester forming this high molecular weight (meth) acrylic copolymer include methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, n-butyl (meth) acrylate and iso. -Butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, n-octyl (meth) acrylate, iso-octyl (meth) acrylate, lauryl (meth) acrylate, stearyl (meth) acrylate, cyclohexyl (meth) acrylate, benzyl Examples thereof include (meth) acrylate, methoxyethyl (meth) acrylate, ethoxymethyl (meth) acrylate, and phenoxyethyl (meth) acrylate. These can be used alone or in combination.
【００１９】また、多官能性化合物に対して反応性を有
する官能基含有モノマーの例としては、（メタ）アクリ
ル酸、β-カルボキシエチルアクリレート、イタコン
酸、クロトン酸、マレイン酸、無水マレイン酸およびマ
レイン酸ブチルなどのカルボキシル基を含有するモノマ
ー、2-ヒドロキシエチル（メタ）アクリレート、2-ヒド
ロキシプロピル（メタ）アクリレート、4-ヒドロキシブ
チル（メタ）アクリレート、クロロ-2-ヒドロキシプロ
ピル（メタ）アクリレート、ジエチレングリコールモノ
（メタ）アクリレートおよびアリルアリコールなどの水
酸基を含有するモノマー、アミノメチル（メタ）アクリ
レート、ジメチルアミノメチル（メタ）アクリレート、
ジメチルアミノエチル（メタ）アクリレート、ジメチル
アミノプロピル（メタ）アクリレートおよびビニルピリ
ジンなどのアミノ基を含有するモノマー、グリシジル
（メタ）アクリレートなどのエポキシ基を含有するモノ
マーおよびアセトアセトキシエチル（メタ）アクリレー
トなどのアセトアセチル基を含有するモノマーなどを挙
げることができる。これらは単独であるいは組み合わせ
て使用することができる。Examples of the functional group-containing monomer having reactivity with a polyfunctional compound include (meth) acrylic acid, β-carboxyethyl acrylate, itaconic acid, crotonic acid, maleic acid, maleic anhydride and Carboxyl group-containing monomers such as butyl maleate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, chloro-2-hydroxypropyl (meth) acrylate, Monomers containing hydroxyl groups such as diethylene glycol mono (meth) acrylate and allyl alicol, aminomethyl (meth) acrylate, dimethylaminomethyl (meth) acrylate,
Amino group-containing monomers such as dimethylaminoethyl (meth) acrylate, dimethylaminopropyl (meth) acrylate and vinylpyridine, epoxy group-containing monomers such as glycidyl (meth) acrylate and acetoacetoxyethyl (meth) acrylate Examples thereof include a monomer containing an acetoacetyl group. These can be used alone or in combination.
【００２０】これらの中でもカルボキシル基を含有する
モノマーおよび水酸基を含有するモノマーが好ましい。
高分子量（メタ）アクリル系共重合体は、８０〜９９.
５重量％、好ましくは９０〜９９.５重量％のアルキル
(メタ)アクリル酸エステルと、０.５〜２０重量％、好
ましくは０.５〜１５重量％の多官能性化合物に対する
反応性を有する官能基含有モノマーとの共重合体であ
る。Of these, monomers containing a carboxyl group and monomers containing a hydroxyl group are preferred.
The high molecular weight (meth) acrylic copolymer is 80 to 99.
5% by weight, preferably 90-99.5% by weight of alkyl
It is a copolymer of (meth) acrylic acid ester and 0.5 to 20% by weight, preferably 0.5 to 15% by weight of a functional group-containing monomer having reactivity with a polyfunctional compound.
【００２１】上記のような量で、アルキル（メタ）アク
リル酸エステルと多官能性化合物に対する反応性を有す
る重合性モノマーとを共重合させることにより、多官能
性化合物と結合して良好な接着性を有する共重合体を形
成することができる。By copolymerizing the alkyl (meth) acrylic acid ester and the polymerizable monomer having reactivity with the polyfunctional compound in the amount as described above, the poly (functional compound) is bonded to the poly (functional) compound to have good adhesiveness. Can be formed.
【００２２】本発明の粘着剤組成物を構成する上記高分
子量（メタ）アクリル系共重合体の重量平均分子量は、
１００万以上であることが必要であり、さらに１００万
〜２００万の範囲にあることが好ましい。このように高
分子量の（メタ）アクリル系共重合体を用いることによ
り、基板と偏光板あるいは位相差板と偏光板との間に良
好な接着性を確保し、発泡やハガレを防止することがで
きる。The weight average molecular weight of the above-mentioned high molecular weight (meth) acrylic copolymer constituting the pressure-sensitive adhesive composition of the present invention is
It is necessary to be 1,000,000 or more, and it is preferable to be in the range of 1,000,000 to 2,000,000. By using a high molecular weight (meth) acrylic copolymer in this manner, good adhesion can be secured between the substrate and the polarizing plate or between the retardation plate and the polarizing plate, and foaming and peeling can be prevented. it can.
【００２３】なお、本発明における高分子量（メタ）ア
クリル系共重合体は、（メタ）アクリル酸エステルと多
官能性化合物に対する反応性を有する重合性モノマーと
の共重合体であるが、さらにこの高分子量（メタ）アク
リル系共重合体には、この高分子量（メタ）アクリル系
共重合体の特性を損なわない範囲内で、他の単量体が共
重合していてもよい。The high molecular weight (meth) acrylic copolymer in the present invention is a copolymer of (meth) acrylic acid ester and a polymerizable monomer having reactivity with a polyfunctional compound. The high molecular weight (meth) acrylic copolymer may be copolymerized with other monomers within a range that does not impair the properties of the high molecular weight (meth) acrylic copolymer.
【００２４】ここで共重合することができる他の単量体
の例としては、酢酸ビニル、スチレン、メチルスチレ
ン、ビニルトルエン、アクリロニトリル、（メタ）アク
リルアミドおよびＮ−メチルアクリルアミドなどを挙げ
ることができる。この単量体の重合量は、（メタ）アク
リル酸エステルと多官能性化合物に対する反応性を有す
る重合性モノマーとの合計量１００重量％に対して、通
常は０〜３０重量％は、好ましくは０〜１５重量％であ
る。Examples of other monomers which can be copolymerized here include vinyl acetate, styrene, methylstyrene, vinyltoluene, acrylonitrile, (meth) acrylamide and N-methylacrylamide. The polymerization amount of this monomer is usually 0 to 30% by weight, preferably 0 to 30% by weight, based on 100% by weight of the total amount of the (meth) acrylic acid ester and the polymerizable monomer having reactivity with the polyfunctional compound. It is 0 to 15% by weight.
【００２５】本発明の偏光板用粘着剤は、低分子量（メ
タ）アクリル系（共）重合体を含有している。この低分
子量体（メタ）アクリル系（共）重合体は、多官能性化
合物に対して反応性がないか、あるいは少ない（共）重
合体であり、多官能性化合物と反応性を有する官能基を
有するモノマーから誘導される繰返し単位の量が、高分
子量（メタ）アクリル系共重合体中に存在する官能基を
有するモノマーから誘導される繰返し単位の量に比べて
低い。即ち、この低分子量（メタ）アクリル系（共）重
合体は、（メタ）アクリル酸エステルから誘導される繰
返し単位を主繰返し単位としており、多官能性化合物と
反応性を有する官能基含有モノマーからなる繰返し単位
を含まないか、あるいはその含有量は極めて少ない
（共）重合体である。さらに、この共重合体は、他の単
量体が共重合していてもよい。The pressure-sensitive adhesive for polarizing plate of the present invention contains a low molecular weight (meth) acrylic (co) polymer. This low molecular weight (meth) acrylic (co) polymer is a (co) polymer having no or little reactivity with a polyfunctional compound, and a functional group having reactivity with the polyfunctional compound. The amount of the repeating unit derived from the monomer having a is lower than the amount of the repeating unit derived from the monomer having a functional group present in the high molecular weight (meth) acrylic copolymer. That is, this low molecular weight (meth) acrylic (co) polymer has a repeating unit derived from a (meth) acrylic acid ester as a main repeating unit, and contains a functional group-containing monomer reactive with a polyfunctional compound. Is a (co) polymer containing no or a very small amount of repeating units. Furthermore, this copolymer may be copolymerized with other monomers.
【００２６】低分子量（メタ）アクリル系（共）重合体
の製造の際に使用される（メタ）アクリル酸エステル、
多官能性化合物に対して反応性を有する官能基含有モノ
マーおよび他の単量体は、上記高分子量（メタ）アクリ
ル系共重合体で記載したものが通常使用される。そし
て、この低分子量（メタ）アクリル（共）重合体の重量
平均分子量は３万以下であることが必要であり、さらに
１０００〜２００００の範囲内にあることが好ましい。
このような分子量の（メタ）アクリル系（共）重合体を
使用することにより、本発明の粘着剤組成物は、偏光板
の温度、湿度による寸法変化に対する粘着剤層の追随性
が良好となり、液晶素子が高温高湿条件下で使用され、
偏光板の寸法が変化しても、その寸法変化に粘着剤層が
追随して変動するので、液晶素子の周縁部の明るさと中
心部の明るさとの間に差がなくなり、色むらなどが発生
しなくなる。(Meth) acrylic acid ester used in the production of low molecular weight (meth) acrylic (co) polymers,
As the functional group-containing monomer and other monomer having reactivity with the polyfunctional compound, those described in the above-mentioned high molecular weight (meth) acrylic copolymer are usually used. The weight average molecular weight of the low molecular weight (meth) acrylic (co) polymer needs to be 30,000 or less, and is preferably in the range of 1,000 to 20,000.
By using a (meth) acrylic (co) polymer having such a molecular weight, the pressure-sensitive adhesive composition of the present invention has good followability of the pressure-sensitive adhesive layer with respect to dimensional changes of the polarizing plate due to temperature and humidity. The liquid crystal element is used under high temperature and high humidity conditions,
Even if the dimensions of the polarizing plate change, the adhesive layer will follow the changes in dimension, so there will be no difference between the brightness of the peripheral part of the liquid crystal element and the brightness of the center part, and color unevenness will occur. Will not do.
【００２７】この低分子量体（メタ）アクリル系（共）
重合体は、上記高分子量体（メタ）アクリル系共重合体
に対して２０〜２００重量部、好ましくは３０〜１００
重量部の量で使用される。２０重量部未満であると、偏
光板の寸法変化に対する粘着剤層の追随性が不十分とな
り、色むらが抑えきれず、また２００重量部を超して使
用すると、高温高湿下での接着性が低下し、ハガレを生
じてしまう。This low molecular weight (meth) acrylic (co)
The polymer is 20 to 200 parts by weight, preferably 30 to 100 parts by weight based on the above-mentioned high molecular weight (meth) acrylic copolymer.
Used in parts by weight. If the amount is less than 20 parts by weight, the adhesiveness of the pressure-sensitive adhesive layer to the dimensional change of the polarizing plate will be insufficient and color unevenness cannot be suppressed, and if it is used in excess of 200 parts by weight, adhesion under high temperature and high humidity will occur. The sex is reduced and peeling occurs.
【００２８】さらに、本発明においては、高分子量（メ
タ）アクリル系共重合体と低分子量（メタ）アクリル系
（共）重合体とを上記の割合で混合した際に、両者の混
合物中におけるそれぞれの重合体における、多官能性化
合物(C)に対して反応性を有する官能基含有モノマーか
ら誘導される繰返し単位のモノマーの換算重量の比であ
る官能基分配率が特定の範囲内にあることが必要であ
る。Further, in the present invention, when the high molecular weight (meth) acrylic copolymer and the low molecular weight (meth) acrylic (co) polymer are mixed in the above-mentioned proportions, respectively, in the mixture of both. In the polymer of (1), the functional group distribution ratio, which is the ratio of the reduced weight of the repeating units derived from the functional group-containing monomer having reactivity with the polyfunctional compound (C), is within a specific range. is necessary.
【００２９】この官能基分散率は、次式で表される。
官能基分配率 ＝［低分子量(メタ)アクリル系共重合体
中における多官能性化合物(C)に対して反応性を有する
官能基含有モノマーから誘導される繰返し単位のモノマ
ー換算重量／高分子量(メタ)アクリル系共重合体中にお
ける多官能性化合物(C)に対して反応性を有する官能基
含有モノマーから誘導される繰返し単位のモノマー換算
重量］×１００。This functional group dispersion rate is expressed by the following equation. Distribution of functional group = [(weight equivalent of monomer of repeating unit derived from functional group-containing monomer having reactivity to polyfunctional compound (C) in low molecular weight (meth) acrylic copolymer) / high molecular weight ( Monomer equivalent weight of repeating units derived from a functional group-containing monomer having reactivity with the polyfunctional compound (C) in the (meth) acrylic copolymer] × 100.
【００３０】そして、本発明では、上記官能基分配率が
０〜１５重量％の範囲内にあることが必要であり、さら
に０〜１０重量％の範囲内にあることが好ましい。この
官能基分配率は、後述する架橋剤（Ｃ）（多官能性化合
物）によって形成される架橋構造の形成の仕方を示すも
のであり、低分子量（メタ）アクリル系（共）重合体
は、高分子量（メタ）アクリル系共重合体（Ａ）を形成
する多官能性化合物（Ｃ）に対して反応性を有する官能
基含有モノマーから誘導される繰返し単位の１５重量％
以下、好ましくは１０重量％以下の量で官能基を有する
モノマーから誘導される繰返し単位を有するか、あるい
は、この繰返し単位を有していないのである。このよう
に低分子量（メタ）アクリル系（共）重合体が、多官能
性化合物（Ｃ）に対して反応性を有する官能基含有モノ
マーから誘導される繰返し単位を有しないか、あるいは
有していてもその数が少ないので、低分子量（メタ）ア
クリル系（共）重合体に架橋構造が形成されないかある
いはされにくく、従って、この低分子量（メタ）アクリ
ル系（共）重合体（Ｂ）は、高分子量（メタ）アクリル
系共重合体（Ａ）と多官能性化合物（Ｃ）とによって形
成される三次元架橋構造物中をある程度自由に移動する
ことができる。偏光板と液晶セル基板等との基本的な接
着強度は、主としてこの三次元架橋構造物によって発現
するが、長期間の接着により偏光板と液晶セル基板等と
の間に生ずる内部応力は、この三次元架橋構造物によっ
ては吸収されないので、この内部応力によって内部歪み
が生ずる。本発明の接着剤は、低分子量（メタ）アクリ
ル系（共）重合体（Ｂ）によって、この内部応力を吸収
させることができるのである。即ち、特定重量平均分子
量の低分子量（メタ）アクリル系（共）重合体（Ｂ）を
上記の量で含有し、かつ官能基の分配率が上記範囲内に
ある低分子量（メタ）アクリル系（共）重合体（Ｂ）を
含有することにより、本発明の接着剤組成物によって形
成された接着剤層は、偏光板の経時変化に対応した形態
追随性を有するようになる。この形態追随性の向上によ
って、色むらを抑制することができるのである。In the present invention, the distribution ratio of the functional group needs to be in the range of 0 to 15% by weight, and preferably in the range of 0 to 10% by weight. The distribution ratio of the functional group indicates the method of forming a crosslinked structure formed by the crosslinking agent (C) (polyfunctional compound) described later, and the low molecular weight (meth) acrylic (co) polymer is 15% by weight of a repeating unit derived from a functional group-containing monomer having reactivity with a polyfunctional compound (C) forming a high molecular weight (meth) acrylic copolymer (A)
Hereafter, it preferably has a repeating unit derived from a monomer having a functional group in an amount of 10% by weight or less, or does not have this repeating unit. Thus, the low molecular weight (meth) acrylic (co) polymer has no or no repeating unit derived from a functional group-containing monomer having reactivity with the polyfunctional compound (C). However, since the number is small, a cross-linked structure is not formed or is unlikely to be formed in the low molecular weight (meth) acrylic (co) polymer. Therefore, this low molecular weight (meth) acrylic (co) polymer (B) is It can move to some extent in the three-dimensional crosslinked structure formed by the high molecular weight (meth) acrylic copolymer (A) and the polyfunctional compound (C). The basic adhesive strength between the polarizing plate and the liquid crystal cell substrate is mainly expressed by this three-dimensional crosslinked structure, but the internal stress generated between the polarizing plate and the liquid crystal cell substrate due to long-term adhesion is This internal stress causes internal strain because it is not absorbed by the three-dimensional cross-linked structure. The adhesive of the present invention can absorb this internal stress by the low molecular weight (meth) acrylic (co) polymer (B). That is, the low molecular weight (meth) acrylic (co) polymer (B) containing the low molecular weight (meth) acrylic (co) polymer (B) having a specific weight average molecular weight in the above amount and having a functional group distribution ratio within the above range ( By containing the (co) polymer (B), the adhesive layer formed by the adhesive composition of the present invention has shape conformability corresponding to the change with time of the polarizing plate. By improving the form following property, it is possible to suppress color unevenness.
【００３１】従って、この官能基分配率が１５重量％を
超えると、低分子量（メタ）アクリル系（共）重合体と
多官能性化合物の反応の比率が増加し、高分子量（メ
タ）アクリル系共重合体と多官能性化合物で形成される
三次元架橋構造の量の低下が起こるため、高温高湿下で
の発泡を生じてしまう。Therefore, when the distribution ratio of the functional group exceeds 15% by weight, the ratio of the reaction between the low molecular weight (meth) acrylic (co) polymer and the polyfunctional compound increases, and the high molecular weight (meth) acrylic type is increased. Since the amount of the three-dimensional crosslinked structure formed by the copolymer and the polyfunctional compound is reduced, foaming occurs under high temperature and high humidity.
【００３２】本発明の偏光板用粘着剤は、多官能性化合
物として多官能性化合物を含有する。この化合物の有す
る官能基は、上記（メタ）アクリル系重合体の反応性を
有する官能基と反応するものであり、一分子内に官能基
を少なくとも２個、好ましくは２〜４個有している。The pressure-sensitive adhesive for polarizing plate of the present invention contains a polyfunctional compound as the polyfunctional compound. The functional group of this compound reacts with the reactive functional group of the (meth) acrylic polymer, and has at least two, preferably 2 to 4 functional groups in one molecule. There is.
【００３３】このような多官能性化合物の例としては、
イソシアネート系化合物、エポキシ系化合物、アミン系
化合物、金属キレート系化合物およびアジリジン系化合
物などを挙げることができる。Examples of such polyfunctional compounds include:
Examples thereof include an isocyanate compound, an epoxy compound, an amine compound, a metal chelate compound, and an aziridine compound.
【００３４】イソシアネート系化合物の例としては、ト
リレンジイソシアネート、ヘキサメチレンジイソシアネ
ート、イソホロンジイソシアネート、キシリレンジイソ
シアネート、水添キシリレンジイソシアネート、ジフェ
ニルメタンジイソシアネート、水添ジフェニルメタンジ
イソシアネート、テトラメチルキシリレンジイソシアネ
ート、ナフタレンジイソシアネート、トリフェニルメタ
ントリイソシアネート、ポリメチレンポリフェニルイソ
シアネートおよびこれらのトリメチロールプロパンなど
ポリオールとのアダクト体などを挙げることができる。Examples of the isocyanate compound include tolylene diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, xylylene diisocyanate, hydrogenated xylylene diisocyanate, diphenylmethane diisocyanate, hydrogenated diphenylmethane diisocyanate, tetramethylxylylene diisocyanate, naphthalene diisocyanate, triphenylene diisocyanate. Examples thereof include phenylmethane triisocyanate, polymethylene polyphenyl isocyanate, and adducts thereof with polyols such as trimethylolpropane.
【００３５】また、エポキシ系化合物の例としては、ビ
スフェノールＡ、エピクロルヒドリン型のエポキシ系樹
脂、エチレングリコールグリシジルエーテル、ポリエチ
レングリコールジグリシジルエーテル、グリセリンジグ
リシジルエーテル、グリセリントリグリシジルエーテ
ル、1,6-ヘキサンジオールジグリシジルエーテル、トリ
メチロールプロパントリグリシジルエーテル、ジグリシ
ジルアニリン、ジグリシジルアミン、N,N,N',N'-テトラ
グリシジル-m-キシレンジアミンおよび1,3-ビス(N,N'-
ジグリシジルアミノメチル)シクロヘキサンなどを挙げ
ることができる。Examples of epoxy compounds include bisphenol A, epichlorohydrin type epoxy resin, ethylene glycol glycidyl ether, polyethylene glycol diglycidyl ether, glycerin diglycidyl ether, glycerin triglycidyl ether, 1,6-hexanediol. Diglycidyl ether, trimethylolpropane triglycidyl ether, diglycidyl aniline, diglycidyl amine, N, N, N ', N'-tetraglycidyl-m-xylenediamine and 1,3-bis (N, N'-
Examples thereof include diglycidylaminomethyl) cyclohexane.
【００３６】さらに、アミン系化合物の例としては、ヘ
キサメチレンジアミン、トリエチルジアミン、ポリエチ
レンイミン、ヘキサメチレンテトラミン、ジエチレント
リアミン、トリエチルテトラミン、イソホロンジアミ
ン、アミノ樹脂およびメチレン樹脂などを挙げることが
できる。Further, examples of amine compounds include hexamethylenediamine, triethyldiamine, polyethyleneimine, hexamethylenetetramine, diethylenetriamine, triethyltetramine, isophoronediamine, amino resins and methylene resins.
【００３７】またさらに、金属キレート化合物の例とし
ては、アルミニウム、鉄、銅、亜鉛、スズ、チタン、ニ
ッケル、アンチモン、マグネシウム、バナジウム、クロ
ムおよびジルコニウムなどの多価金属がアセチルアセト
ンやアセト酢酸エチルに配位した化合物などを挙げるこ
とができる。Further, as an example of the metal chelate compound, a polyvalent metal such as aluminum, iron, copper, zinc, tin, titanium, nickel, antimony, magnesium, vanadium, chromium and zirconium is distributed in acetylacetone or ethyl acetoacetate. The compound etc. which were coordinated can be mentioned.
【００３８】さらに、アジリジン系化合物の例として
は、N,N'-ジフェニルメタン-4,4'-ビス(1-アジリジンカ
ルボキサイド)、N,N'-トルエン-2,4-ビス(1-アジリジン
カルボキサミド)、トリエチレンメラミン、ビスイソフ
タロイル-1-(2-メチルアジリジン)、トリ-1-アジリジニ
ルホスフィンオキサイド、N,N'-ヘキサメチレン-1.6-ビ
ス(1-アジリジンカルボキサイド)、トリメチロールプロ
パン-トリ-β-アジリジニルプロピオネートおよびテト
ラメチロールメタン-トリ-β-アジリジニルプロピオネ
ートなどを挙げることができる。Further, examples of the aziridine compound include N, N'-diphenylmethane-4,4'-bis (1-aziridinecarboxide), N, N'-toluene-2,4-bis (1-aziridine. Carboxamide), triethylenemelamine, bisisophthaloyl-1- (2-methylaziridine), tri-1-aziridinylphosphine oxide, N, N'-hexamethylene-1.6-bis (1-aziridinecarboxide), Examples thereof include trimethylolpropane-tri-β-aziridinylpropionate and tetramethylolmethane-tri-β-aziridinylpropionate.
【００３９】このような多官能性化合物は、上記高分子
量（メタ）アクリル系共重合体１００重量部に対して、
通常は０.００５〜５重量部、好ましくは０.０１〜３重
量部の量で使用される。このような量で多官能性化合物
を使用することにより、上記高分子量（メタ）アクリル
系共重合体との間で好適な三次元架橋構造が形成され
る。なお、これら多官能性化合物は、単独であるいは組
み合わせて使用することができる。Such a polyfunctional compound is added to 100 parts by weight of the above-mentioned high molecular weight (meth) acrylic copolymer.
It is usually used in an amount of 0.005 to 5 parts by weight, preferably 0.01 to 3 parts by weight. By using the polyfunctional compound in such an amount, a suitable three-dimensional crosslinked structure is formed with the above-mentioned high molecular weight (meth) acrylic copolymer. In addition, these polyfunctional compounds can be used individually or in combination.
【００４０】本発明の偏光板用粘着剤を構成する高分子
量（メタ）アクリル系共重合体および低分子量（メタ）
アクリル系（共）重合体の製造には、公知の任意の方法
を採用することができる。High molecular weight (meth) acrylic copolymer and low molecular weight (meth) which compose the pressure-sensitive adhesive for polarizing plate of the present invention.
Any known method can be adopted for producing the acrylic (co) polymer.
【００４１】例えば高分子量（メタ）アクリル系共重合
体は、原料モノマー１００重量部に対して、０.０１〜
１重量部の重合開始剤（アゾビスイソビチロニトリル、
アゾビスシクロヘキサンカルボニトリルなどのアゾ系重
合開始剤、過酸化ベンゾイル、過酸化アセチルなどの過
酸化物、ジフェニルケトン、2-ヒドロキシ-2-メチル-1-
フェニル-プロパン-1-オンなどの光重合開始剤など）を
用い、塊状重合、溶液重合、乳化重合、懸濁重合などの
方法により合成され、好ましくは溶液重合で合成され
る。For example, the high molecular weight (meth) acrylic copolymer is 0.01 to 100 parts by weight of the raw material monomer.
1 part by weight of a polymerization initiator (azobisisobityronitrile,
Azo-based polymerization initiators such as azobiscyclohexanecarbonitrile, benzoyl peroxide, peroxides such as acetyl peroxide, diphenyl ketone, 2-hydroxy-2-methyl-1-
It is synthesized by a method such as bulk polymerization, solution polymerization, emulsion polymerization or suspension polymerization using a photopolymerization initiator such as phenyl-propan-1-one), and preferably solution polymerization.
【００４２】溶液重合法の場合、重合溶媒として酢酸エ
チル、トルエン、ヘキサン、アセトンなどが用いられ、
反応温度は５０〜１５０℃、好ましくは５０〜１１０
℃、反応時間は３〜１５時間、好ましくは５〜１０時間
である。In the case of the solution polymerization method, ethyl acetate, toluene, hexane, acetone or the like is used as a polymerization solvent,
The reaction temperature is 50 to 150 ° C., preferably 50 to 110.
C., the reaction time is 3 to 15 hours, preferably 5 to 10 hours.
【００４３】また、低分子量（メタ）アクリル系（共）
重合体は、高分子量アクリル系共重合体と同様、塊状重
合、溶液重合、乳化重合、懸濁重合などの方法により合
成され、好ましくは、溶液重合で合成される。但し、重
量平均分子量３万以下にするため、重合開始剤の使用量
を高分子量アクリル系共重合体の場合の１０〜１００倍
程度にし、さらに好ましくはラウリルメルカプタン、n-
ドデシルメルカプタン、n-オクチルメルカプタンなどの
メルカプタン、α-メチルスチレンダイマーおよびリモ
ネンなどの連鎖移動剤が使用される。Further, low molecular weight (meth) acrylic (co)
The polymer, like the high molecular weight acrylic copolymer, is synthesized by a method such as bulk polymerization, solution polymerization, emulsion polymerization or suspension polymerization, preferably solution polymerization. However, in order to reduce the weight average molecular weight to 30,000 or less, the amount of the polymerization initiator used is about 10 to 100 times that of the high molecular weight acrylic copolymer, and more preferably lauryl mercaptan, n-
Chain transfer agents such as mercaptans such as dodecyl mercaptan, n-octyl mercaptan, α-methylstyrene dimer and limonene are used.
【００４４】本発明の偏光板用粘着剤は、上記のように
して製造した高分子量（メタ）アクリル系共重合体、低
分子量（メタ）アクリル系（共）重合体および多官能性
化合物を混合することにより製造することができる。The pressure-sensitive adhesive for polarizing plate of the present invention is a mixture of the high molecular weight (meth) acrylic copolymer, the low molecular weight (meth) acrylic (co) polymer and the polyfunctional compound produced as described above. It can be manufactured by
【００４５】この際、低分子量（メタ）アクリル系
（共）重合体は、上記高分子量（メタ）アクリル系共重
合体１００重量部に対して、２０〜２００重量部、好ま
しくは３０〜１５０重量部、多官能性化合物は、上記高
分子量（メタ）アクリル系共重合体１００重量部に対し
て、０.００５〜５重量部、好ましくは０.０１〜３重量
部の量で含有する。In this case, the low molecular weight (meth) acrylic (co) polymer is 20 to 200 parts by weight, preferably 30 to 150 parts by weight, relative to 100 parts by weight of the above high molecular weight (meth) acrylic copolymer. The polyfunctional compound is contained in an amount of 0.005 to 5 parts by weight, preferably 0.01 to 3 parts by weight, based on 100 parts by weight of the high molecular weight (meth) acrylic copolymer.
【００４６】本発明の偏光板用粘着剤は、上記のように
高分子量（メタ）アクリル系共重合体、低分子量（メ
タ）アクリル系（共）重合体および多官能性化合物から
なるが、さらに、この偏光板用粘着剤には、通常粘着剤
に配合される、耐候安定剤、タッキファイヤー、可塑
剤、軟化剤、染料、顔料、シランカップリング剤および
無機フィラー等を配合することができる。The polarizing plate pressure-sensitive adhesive of the present invention comprises a high molecular weight (meth) acrylic copolymer, a low molecular weight (meth) acrylic (co) polymer and a polyfunctional compound as described above. The pressure-sensitive adhesive for polarizing plate may contain a weather resistance stabilizer, a tackifier, a plasticizer, a softening agent, a dye, a pigment, a silane coupling agent, an inorganic filler and the like, which are usually mixed with the pressure-sensitive adhesive.
【００４７】本発明の偏光板は、偏光フィルムの一方の
面に、上記粘着剤から形成された粘着剤層を積層する。
本発明で使用される偏光フィルムとしては、従来公知の
偏光フィルムを使用することができる。In the polarizing plate of the present invention, a pressure-sensitive adhesive layer formed of the above-mentioned pressure-sensitive adhesive is laminated on one surface of the polarizing film.
As the polarizing film used in the present invention, a conventionally known polarizing film can be used.
【００４８】例えば、ポリビニルアルコール、ポリビニ
ルホルマール、ポリビニルアセタールおよびエチレン・
酢酸ビニル共重合体の鹸化物等のポリビニルアルコール
系樹脂からなるフィルムに、ヨウ素あるいは二色性染料
等の偏光成分をが含有させて延伸することにより得られ
るフィルムに、三酢酸セルロース等のセルロース系フィ
ルム、ポリカーボネートフィルム、ポリエーテルスルホ
ン系フィルム等の保護フィルムが積層された多層フィル
ムなどを使用することができる。For example, polyvinyl alcohol, polyvinyl formal, polyvinyl acetal and ethylene.
A film made of a polyvinyl alcohol-based resin such as a saponified product of vinyl acetate copolymer containing a polarizing component such as iodine or a dichroic dye and stretched, a cellulose-based film such as cellulose triacetate A multilayer film in which protective films such as a film, a polycarbonate film and a polyether sulfone film are laminated can be used.
【００４９】このような偏光フィルムに粘着剤層を形成
する方法に特に制限はなく、この偏光フィルム表面に直
接バーコーター等を用いて上記粘着剤を塗布し乾燥させ
る方法を採用することもできるが、上記粘着剤を一旦剥
離性基材表面に塗布し乾燥させた後、この剥離性基材表
面に形成された粘着剤層を偏光フィルム表面に転写し、
次いで熟成させる方法を採用することが好ましい。The method of forming the pressure-sensitive adhesive layer on such a polarizing film is not particularly limited, and a method of directly applying the pressure-sensitive adhesive to the surface of the polarizing film using a bar coater or the like and drying it can also be adopted. , The adhesive is once applied to a peelable substrate surface and dried, and then the adhesive layer formed on the peelable substrate surface is transferred to a polarizing film surface,
Then, it is preferable to adopt a method of aging.
【００５０】こうして形成される粘着剤層の厚さは、乾
燥厚で通常は１０〜１００μｍ、好ましくは２０〜５０
μｍの範囲内にある。なお、この粘着剤層は、偏光フィ
ルムの少なくとも一方の面に形成されていればよく、従
って本発明では偏光フィルムの両面にこの粘着剤層を形
成することもできる。The pressure-sensitive adhesive layer thus formed has a dry thickness of usually 10 to 100 μm, preferably 20 to 50 μm.
It is in the range of μm. The pressure-sensitive adhesive layer only needs to be formed on at least one surface of the polarizing film. Therefore, in the present invention, the pressure-sensitive adhesive layer can be formed on both surfaces of the polarizing film.
【００５１】また、本発明の偏光板には、例えば保護
層、反射層、防眩層等の他の機能を有する層が積層され
ていてもよい。The polarizing plate of the present invention may be laminated with layers having other functions such as a protective layer, a reflective layer and an antiglare layer.
【００５２】[0052]
【発明の効果】本発明の偏光板用粘着剤は、重量平均分
子量１００万以上高分子量（メタ）アクリル系共重合体
と、重量平均分子量３万以下の低分子量（メタ）アクリ
ル系（共）重合体と、多官能性化合物とからなり、この
多官能性化合物は主として高分子量（メタ）アクリル系
共重合体と結合して三次元架橋構造を形成する。一方、
低分子量（メタ）アクリル系（共）重合体は、多官能性
化合物と反応しないかあるいは反応しても三次元架橋構
造を形成しにくいので、上記のように形成された三次元
架橋構造中に独自に存在する。このように多官能性化合
物と高分子量（メタ）アクリル系共重合物とから形成さ
れた三次元架橋構造と、この三次元架橋構造中に独自に
存在する低分子量（メタ）アクリル系（共）重合体によ
り構成される粘着剤層は、温度および湿度に起因する偏
光板の寸法変化に追随することが可能になる。The pressure-sensitive adhesive for polarizing plate of the present invention comprises a high-molecular weight (meth) acrylic copolymer having a weight average molecular weight of 1,000,000 or more and a low molecular weight (meth) acrylic (co) polymer having a weight average molecular weight of 30,000 or less. It is composed of a polymer and a polyfunctional compound, and this polyfunctional compound mainly bonds with a high molecular weight (meth) acrylic copolymer to form a three-dimensional crosslinked structure. on the other hand,
The low molecular weight (meth) acrylic (co) polymer does not react with the polyfunctional compound or does not easily form a three-dimensional crosslinked structure even when reacted, so that the three-dimensional crosslinked structure formed as described above Exist independently. Thus, the three-dimensional crosslinked structure formed from the polyfunctional compound and the high molecular weight (meth) acrylic copolymer, and the low molecular weight (meth) acrylic (co) polymer uniquely present in the three-dimensional crosslinked structure The pressure-sensitive adhesive layer composed of the polymer can follow the dimensional change of the polarizing plate due to temperature and humidity.
【００５３】従って、本発明の粘着剤を用いて偏光フィ
ルムを液晶素子の位相差板あるいは基板に貼着すること
により、高温高湿下における繰り返し使用によっても、
粘着剤層に発泡が生ずることなく、また、界面剥離等が
発生することがなく、しかも周縁部と中央部との色むら
の少ない液晶素子を形成することができる。Therefore, by sticking a polarizing film to the retardation plate or substrate of a liquid crystal element using the pressure-sensitive adhesive of the present invention, it can be repeatedly used under high temperature and high humidity.
It is possible to form a liquid crystal element in which foaming does not occur in the pressure-sensitive adhesive layer, interfacial peeling or the like does not occur, and color unevenness between the peripheral portion and the central portion is small.
【００５４】[0054]
【実施例】次に本発明の実施例を示して本発明をさらに
詳細に説明するが、本発明はこれらによって限定される
ものではない。The present invention will now be described in more detail with reference to examples of the present invention, but the present invention is not limited thereto.
【００５５】（ポリマー溶液１）n-ブチルアクリレート
９５重量部、アクリル酸５重量部、酢酸エチル１００重
量部および過酸化ベンゾイル０.２重量部を反応容器に
入れ、この反応溶液器内の空気を窒素ガスで置換した
後、撹拌下に窒素雰囲気中で、この反応溶液を６６℃に
昇温させ、１０時間反応させた。反応後、酢酸エチルで
希釈し、固形分２０重量％の（メタ）アクリル系ポリマ
ー溶液を得た。(Polymer Solution 1) 95 parts by weight of n-butyl acrylate, 5 parts by weight of acrylic acid, 100 parts by weight of ethyl acetate and 0.2 parts by weight of benzoyl peroxide were placed in a reaction vessel, and the air in the reaction solution vessel was replaced with air. After purging with nitrogen gas, the reaction solution was heated to 66 ° C. in a nitrogen atmosphere with stirring and reacted for 10 hours. After the reaction, the mixture was diluted with ethyl acetate to obtain a (meth) acrylic polymer solution having a solid content of 20% by weight.
【００５６】（ポリマー溶液２）n-ブチルアクリレート
８９重量部、ベンジルアクリレート１０重量部、2-ヒド
ロキシエチルアクリレート１重量部、酢酸エチル１００
重量部、およびアゾビスイソブチロニトリル０.２重量
部を反応容器に入れ、この反応溶液器内の空気を窒素ガ
スで置換した後、撹拌下に窒素雰囲気中で、この反応溶
液を６６℃に昇温させ、１０時間反応させた。反応後、
酢酸エチルで希釈し、固形分２２重量％の（メタ）アク
リル系ポリマー溶液を得た。(Polymer solution 2) 89 parts by weight of n-butyl acrylate, 10 parts by weight of benzyl acrylate, 1 part by weight of 2-hydroxyethyl acrylate, 100 parts of ethyl acetate
Parts by weight and 0.2 parts by weight of azobisisobutyronitrile were placed in a reaction vessel, the air in the reaction solution vessel was replaced with nitrogen gas, and the reaction solution was stirred at 66 ° C. in a nitrogen atmosphere. The temperature was raised to 10, and the reaction was performed for 10 hours. After the reaction
It was diluted with ethyl acetate to obtain a (meth) acrylic polymer solution having a solid content of 22% by weight.
【００５７】（ポリマー溶液３）n-ブチルアクリレート
９０重量部、ベンジルアクリレート１０重量部、酢酸エ
チル１００重量部、およびアゾビスイソブチロニトリル
０.２重量部を反応容器に入れ、この反応溶液器内の空
気を窒素ガスで置換した後、撹拌下に窒素雰囲気中で、
この反応溶液を６６℃に昇温させ、１５時間反応させ
た。反応後、酢酸エチルで希釈し、固形分２２重量％の
（メタ）アクリル系ポリマー溶液得た。(Polymer Solution 3) 90 parts by weight of n-butyl acrylate, 10 parts by weight of benzyl acrylate, 100 parts by weight of ethyl acetate, and 0.2 parts by weight of azobisisobutyronitrile were placed in a reaction vessel, and this reaction solution container was used. After replacing the air inside with nitrogen gas, in a nitrogen atmosphere with stirring,
The reaction solution was heated to 66 ° C. and reacted for 15 hours. After the reaction, the mixture was diluted with ethyl acetate to obtain a (meth) acrylic polymer solution having a solid content of 22% by weight.
【００５８】（ポリマー溶液４）n-ブチルアクリレート
９５重量部、アクリル酸５重量部、酢酸エチル１２０重
量部、トルエン３０重量部および過酸化ベンゾイル０.
３重量部を反応容器に入れ、この反応器内の空気を窒素
ガスで置換した後、撹拌下に窒素雰囲気中で、この反応
溶液を７０℃に昇温させ、１０時間反応させた。反応
後、酢酸エチルで希釈し、固形分２５重量％の（メタ）
アクリル系ポリマー溶液得た。(Polymer solution 4) 95 parts by weight of n-butyl acrylate, 5 parts by weight of acrylic acid, 120 parts by weight of ethyl acetate, 30 parts by weight of toluene, and benzoyl peroxide (0.1 parts by weight).
After 3 parts by weight was placed in a reaction vessel and the air in the reactor was replaced with nitrogen gas, the reaction solution was heated to 70 ° C. in a nitrogen atmosphere with stirring and reacted for 10 hours. After the reaction, dilute with ethyl acetate to obtain a solid content of 25% by weight (meth)
An acrylic polymer solution was obtained.
【００５９】（ポリマー溶液５）n-ブチルアクリレート
６５重量部、メチルメタクリレート３０重量部、アクリ
ルアマイド５重量部、トルエン１００重量部、アゾビス
イソブチロニトリル２重量部およびラウリルメルカプタ
ン２重量部を反応容器に入れ、この反応溶液器内の空気
を窒素ガスで置換した後、撹拌下に窒素雰囲気中で、こ
の反応溶液を１１０℃に昇温させ、６時間反応させた。
反応後、トルエンで希釈し、固形分４０重量％の（メ
タ）アクリル系ポリマー溶液得た。(Polymer solution 5) 65 parts by weight of n-butyl acrylate, 30 parts by weight of methyl methacrylate, 5 parts by weight of acrylate, 100 parts by weight of toluene, 2 parts by weight of azobisisobutyronitrile and 2 parts by weight of lauryl mercaptan were reacted. After being placed in a container and replacing the air in the reaction solution vessel with nitrogen gas, the reaction solution was heated to 110 ° C. in a nitrogen atmosphere with stirring and reacted for 6 hours.
After the reaction, the mixture was diluted with toluene to obtain a (meth) acrylic polymer solution having a solid content of 40% by weight.
【００６０】（ポリマー溶液６）n-ブチルアクリレート
６５重量部、メチルメタクリレート３０重量部、アクリ
ルアマイド５重量部、トルエン１００重量部およびアゾ
ビスイソブチロニトリル２重量部を反応容器に入れ、こ
の反応溶液器内の空気を窒素ガスで置換した後、撹拌下
に窒素雰囲気中で、この反応溶液を１１０℃に昇温さ
せ、６時間反応させた。反応後、トルエンで希釈し、固
形分４０重量％の（メタ）アクリル系ポリマー溶液得
た。(Polymer solution 6) 65 parts by weight of n-butyl acrylate, 30 parts by weight of methyl methacrylate, 5 parts by weight of acrylate, 100 parts by weight of toluene and 2 parts by weight of azobisisobutyronitrile were placed in a reaction vessel and the reaction was carried out. After replacing the air in the solution container with nitrogen gas, the temperature of this reaction solution was raised to 110 ° C. in a nitrogen atmosphere with stirring, and the reaction was carried out for 6 hours. After the reaction, the mixture was diluted with toluene to obtain a (meth) acrylic polymer solution having a solid content of 40% by weight.
【００６１】（ポリマー溶液７）メトキシエチルアクリ
レート５２.５重量部、イソブチルメタクリレート４７
重量部、２-ヒドロキシエチルアクリレート０.５重量
部、トルエン１００重量部、過酸化ベンゾイル３重量部
およびα-メチルスチレンダイマー３重量部を反応容器
に入れ、この反応溶液器内の空気を窒素ガスで置換した
後、撹拌下に窒素雰囲気中で、この反応溶液を１１０℃
に昇温させ、６時間反応させた。反応後、トルエンで希
釈し、固形分４０重量％の（メタ）アクリル系ポリマー
溶液得た。(Polymer solution 7) 52.5 parts by weight of methoxyethyl acrylate, 47 of isobutyl methacrylate
Parts by weight, 0.5 parts by weight of 2-hydroxyethyl acrylate, 100 parts by weight of toluene, 3 parts by weight of benzoyl peroxide and 3 parts by weight of α-methylstyrene dimer were placed in a reaction vessel, and the air in the reaction solution vessel was replaced with nitrogen gas. After replacement with, the reaction solution was stirred at 110 ° C. in a nitrogen atmosphere.
The temperature was raised to, and the reaction was performed for 6 hours. After the reaction, the mixture was diluted with toluene to obtain a (meth) acrylic polymer solution having a solid content of 40% by weight.
【００６２】（ポリマー溶液８）メトキシエチルアクリ
レート４８重量部、イソブチルメタクリレート４７重量
部、２-ヒドロキシエチルアクリレート５重量部、トル
エン１００重量部、過酸化ベンゾイル３重量部およびα
-メチルスチレンダイマー３重量部を反応容器に入れ、
この反応溶液器内の空気を窒素ガスで置換した後、撹拌
下に窒素雰囲気中で、この反応溶液を１１０℃に昇温さ
せ、６時間反応させた。反応後、トルエンで希釈し、固
形分４０重量％の（メタ）アクリル系ポリマー溶液得
た。(Polymer solution 8) 48 parts by weight of methoxyethyl acrylate, 47 parts by weight of isobutyl methacrylate, 5 parts by weight of 2-hydroxyethyl acrylate, 100 parts by weight of toluene, 3 parts by weight of benzoyl peroxide and α
-Add 3 parts by weight of methyl styrene dimer to the reaction vessel,
After replacing the air in the reaction solution vessel with nitrogen gas, the reaction solution was heated to 110 ° C. in a nitrogen atmosphere with stirring and reacted for 6 hours. After the reaction, the mixture was diluted with toluene to obtain a (meth) acrylic polymer solution having a solid content of 40% by weight.
【００６３】（ポリマー溶液９）n-ブチルアクリレート
９０重量部、ベンジルアクリレート１０重量部、トルエ
ン１００重量部、アゾビスイソブチロニトリル２重量部
およびラウリルメルカプタン２重量部を反応容器に入
れ、この反応溶液器内の空気を窒素ガスで置換した後、
撹拌下に窒素雰囲気中で、この反応溶液を１１０℃に昇
温させ、６時間反応させた。反応後、トルエンで希釈
し、固形分４０重量％の（メタ）アクリル系ポリマー溶
液得た。(Polymer solution 9) 90 parts by weight of n-butyl acrylate, 10 parts by weight of benzyl acrylate, 100 parts by weight of toluene, 2 parts by weight of azobisisobutyronitrile and 2 parts by weight of lauryl mercaptan were placed in a reaction vessel and the reaction was carried out. After replacing the air in the solution container with nitrogen gas,
In a nitrogen atmosphere with stirring, the reaction solution was heated to 110 ° C. and reacted for 6 hours. After the reaction, the mixture was diluted with toluene to obtain a (meth) acrylic polymer solution having a solid content of 40% by weight.
【００６４】上記ポリマー溶液における各ポリマーのス
チレン換算による重量平均分子量（Ｍｗ）をゲル浸透ク
ロマトグラフ法（ＧＰＣ）から求めた。なお、測定条件
は以下の通りである。The styrene-equivalent weight average molecular weight (Mw) of each polymer in the polymer solution was determined by gel permeation chromatography (GPC). The measurement conditions are as follows.
【００６５】 装置名：東ソー(株)製、ＨＬＣ-８１２０ カラム：東ソー(株)製、Ｇ７０００ＨＸＬ 7.8mmID×30cm １本 ＧＭＨＸＬ 7.8mmID×30cm ２本 Ｇ２５００ＨＸＬ 7.8mmID×30cm １本 サンプル濃度：１.５ｍｇ／ｍｌになるようにテトラヒドロフランで希釈 移動相溶媒：テトラヒドロフラン 流量：１.０ｍｌ／ｍｉｎ カラム温度：４０℃ 結果を表１に示す。[0065] Device name: Tosoh Corp., HLC-8120 Column: Tosoh Corporation, G7000HXL 7.8mm ID x 30cm 1 GMHXL 7.8mm ID x 30cm 2 Pieces G2500HXL 7.8mm ID x 30cm 1 Piece Sample concentration: Diluted with tetrahydrofuran to 1.5 mg / ml Mobile phase solvent: Tetrahydrofuran Flow rate: 1.0 ml / min Column temperature: 40 ° C The results are shown in Table 1.
【００６６】[0066]
【実施例１】ポリマー溶液１とポリマー溶液５を固形分
比１００重量部／１５０重量部になるように混合し、こ
れに多官能性化合物としてエポキシ系化合物（商品名：
テトラッドＸ、三菱ガス化学(株)製）固形分０.０２重
量部を添加し、よく撹拌して偏光板用粘着剤溶液を得
た。Example 1 Polymer solution 1 and polymer solution 5 were mixed at a solid content ratio of 100 parts by weight / 150 parts by weight, and an epoxy compound (trade name: as a polyfunctional compound) was added thereto.
Tetrad X, manufactured by Mitsubishi Gas Chemical Co., Inc.) 0.02 part by weight of solid content was added and well stirred to obtain a pressure-sensitive adhesive solution for a polarizing plate.
【００６７】なお多官能性化合物に対して反応性を有す
る官能基量の比率は、ポリマー溶液５／ポリマー溶液１
＝０重量％である。このようにして得られた偏光板用粘
着剤溶液をポリエステル製剥離フィルムに塗布した後、
乾燥させた。このとき、乾燥後の塗布厚は、２５μｍに
なるように調整した。The ratio of the amount of functional groups having reactivity with the polyfunctional compound is as follows: polymer solution 5 / polymer solution 1
= 0% by weight. After applying the polarizing plate pressure-sensitive adhesive solution thus obtained to a polyester release film,
Dried. At this time, the coating thickness after drying was adjusted to be 25 μm.
【００６８】次いでこの剥離フィルム上に塗布された粘
着剤を２００μｍの偏光フィルム上に転写し、温度２３
℃、湿度６５％の条件で７日間熟成させて本発明の偏光
板を得た。Next, the pressure-sensitive adhesive applied on this release film was transferred onto a 200 μm polarizing film, and the temperature was adjusted to 23.
The polarizing plate of the present invention was obtained by aging for 7 days under the conditions of ° C and a humidity of 65%.
【００６９】粘着剤層が設けられた偏光板を、吸収軸が
偏光板長辺に対して４５°になるように６０ｍｍ×１０
０ｍｍに裁断して、この偏光板をガラス板の片面に、５
０℃圧力５ｋｇ／ｃｍ2の条件で２０分保持して接着さ
せた。A polarizing plate provided with an adhesive layer was 60 mm × 10 so that the absorption axis was 45 ° with respect to the long side of the polarizing plate.
Cut it to 0 mm and put this polarizing plate on one side of the glass plate.
It was held for 20 minutes under the conditions of 0 ° C. and a pressure of 5 kg / cm 2 for adhesion.
【００７０】こうして得られたサンプルを１００℃およ
び８０℃９０％の条件下に５００時間放置し、発泡、ハ
ガレの発生状態を目視観察にて評価した。結果を表２に
示す。The sample thus obtained was left to stand under conditions of 100 ° C. and 80 ° C. 90% for 500 hours, and the state of foaming and peeling was evaluated by visual observation. The results are shown in Table 2.
【００７１】また、同様に調製したサンプルをガラス板
の両面に、吸収軸が直行するように配置して、５０℃圧
力５ｋｇ／ｃｍ2の条件で２０分保持して接着させた。
こうして得られたサンプルを１００℃の条件下に５００
時放置し、色むらの発生状態を目視観察にて評価し、ま
た、偏光板の長辺における接着位置のずれ距離をノギス
にて測定した。結果を表２に示す。Samples prepared in the same manner were arranged on both sides of a glass plate so that the absorption axis was perpendicular to each other, and held for 20 minutes under the condition of 50 ° C. and a pressure of 5 kg / cm 2 to bond them.
The sample thus obtained is subjected to 500 ° C. under the condition of 100 ° C.
Then, the state of occurrence of color unevenness was evaluated by visual observation, and the displacement distance of the bonding position on the long side of the polarizing plate was measured with a caliper. The results are shown in Table 2.
【００７２】[0072]
【実施例２】ポリマー溶液２とポリマー溶液７とを固形
分比１００重量部／２５重量部になるように混合し、こ
れに多官能性化合物としてポリイソシアネート系化合物
（商品名：コロネートＬ、日本ポリウレタン(株)製）固
形分１.０重量部を添加し、よく撹拌して偏光板用粘着
剤溶液を得た。Example 2 Polymer solution 2 and polymer solution 7 were mixed at a solid content ratio of 100 parts by weight / 25 parts by weight, and a polyisocyanate compound (trade name: Coronate L, Japan Polyurethane Co., Ltd. solid content 1.0 part by weight was added and well stirred to obtain an adhesive solution for a polarizing plate.
【００７３】なお多官能性化合物に対して反応性を有す
る官能基量の比率は、ポリマー溶液７／ポリマー溶液２
＝１２.５重量％である。このようにして得られた偏光
板用粘着剤を用い、実施例１と同様にして粘着剤層を設
けた偏光板を調製した。The ratio of the amount of functional groups reactive with the polyfunctional compound is as follows: polymer solution 7 / polymer solution 2
= 12.5% by weight. Using the pressure-sensitive adhesive for polarizing plate thus obtained, a polarizing plate provided with a pressure-sensitive adhesive layer was prepared in the same manner as in Example 1.
【００７４】この偏光板について、実施例１と同様にし
て発泡、ハガレの発生状態を観察した。また、色むらの
発生状態を観察し、偏光板の長辺におけるずれ距離を測
定した。これら結果を表２に示す。With respect to this polarizing plate, foaming and peeling were observed in the same manner as in Example 1. In addition, the occurrence state of color unevenness was observed, and the displacement distance on the long side of the polarizing plate was measured. The results are shown in Table 2.
【００７５】[0075]
【実施例３】ポリマー溶液２とポリマー溶液９とを固形
分比１００重量部／１００重量部になるように混合し、
これに多官能性化合物としてポリイソシアネート系化合
物（商品名：コロネートＨＬ、日本ポリウレタン(株)
製）固形分０.０４重量部を添加し、よく撹拌して偏光
板用粘着剤溶液を得た。Example 3 Polymer solution 2 and polymer solution 9 were mixed in a solid content ratio of 100 parts by weight / 100 parts by weight,
In addition to this, polyisocyanate compounds as polyfunctional compounds (trade name: Coronate HL, Nippon Polyurethane Co., Ltd.)
0.04 part by weight of solid content was added and well stirred to obtain an adhesive solution for polarizing plate.
【００７６】なお多官能性化合物に対して反応性を有す
る官能基量の比率は、ポリマー溶液９／ポリマー溶液２
＝０重量％である。このようにして得られた偏光板用粘
着剤を用い、実施例１と同様にして粘着剤層を設けた偏
光板を調製した。The ratio of the amount of functional groups having reactivity with the polyfunctional compound is as follows: polymer solution 9 / polymer solution 2
= 0% by weight. Using the pressure-sensitive adhesive for polarizing plate thus obtained, a polarizing plate provided with a pressure-sensitive adhesive layer was prepared in the same manner as in Example 1.
【００７７】この偏光板について、実施例１と同様にし
て発泡、ハガレの発生状態を観察した。また、色むらの
発生状態を観察し、偏光板の長辺におけるずれ距離を測
定した。これら結果を表２に示す。With respect to this polarizing plate, foaming and peeling were observed in the same manner as in Example 1. In addition, the occurrence state of color unevenness was observed, and the displacement distance on the long side of the polarizing plate was measured. The results are shown in Table 2.
【００７８】[0078]
【実施例４】ポリマー溶液１とポリマー溶液９とを固形
分比１００重量部／２５重量部になるように混合し、こ
れに多官能性化合物として実施例１で使用したエポキシ
系化合物０.０２重量部を添加し、よく撹拌して偏光板
用粘着剤溶液を得た。Example 4 Polymer solution 1 and polymer solution 9 were mixed in a solid content ratio of 100 parts by weight / 25 parts by weight, and the epoxy compound 0.02 used as a polyfunctional compound in Example 1 was added thereto. Parts by weight were added and well stirred to obtain an adhesive solution for polarizing plate.
【００７９】なお多官能性化合物に対して反応性を有す
る官能基量の比率は、ポリマー溶液９／ポリマー溶液１
＝０重量％である。このようにして得られた偏光板用粘
着剤を用い、実施例１と同様にして粘着剤層を設けた偏
光板を調製した。The ratio of the amount of functional groups reactive with the polyfunctional compound is as follows: polymer solution 9 / polymer solution 1
= 0% by weight. Using the pressure-sensitive adhesive for polarizing plate thus obtained, a polarizing plate provided with a pressure-sensitive adhesive layer was prepared in the same manner as in Example 1.
【００８０】この偏光板について、実施例１と同様にし
て発泡、ハガレの発生状態を観察した。また、色むらの
発生状態を観察し、偏光板の長辺におけるずれ距離を測
定した。これら結果を表２に示す。With respect to this polarizing plate, foaming and peeling were observed in the same manner as in Example 1. In addition, the occurrence state of color unevenness was observed, and the displacement distance on the long side of the polarizing plate was measured. The results are shown in Table 2.
【００８１】[0081]
【比較例１】ポリマー溶液１とポリマー溶液５を固形分
比１００重量部／１０重量部になるように混合し、これ
に多官能性化合物として実施例１で使用したエポキシ系
化合物固形分０.０２重量部を添加し、よく撹拌して偏
光板用粘着剤溶液を得た。Comparative Example 1 Polymer solution 1 and polymer solution 5 were mixed at a solid content ratio of 100 parts by weight / 10 parts by weight, and the epoxy compound solid content used in Example 1 as a polyfunctional compound was 0.1. 02 parts by weight was added and well stirred to obtain an adhesive solution for a polarizing plate.
【００８２】なお多官能性化合物に対して反応性を有す
る官能基量の比率は、ポリマー溶液５／ポリマー溶液１
＝０重量％である。このようにして得られた偏光板用粘
着剤を用い、実施例１と同様にして粘着剤層を設けた偏
光板を調製した。The ratio of the amount of functional groups reactive with the polyfunctional compound is 5 polymer solution / 1 1 polymer solution.
= 0% by weight. Using the pressure-sensitive adhesive for polarizing plate thus obtained, a polarizing plate provided with a pressure-sensitive adhesive layer was prepared in the same manner as in Example 1.
【００８３】この偏光板について、実施例１と同様にし
て発泡、ハガレの発生状態を観察した。また、色むらの
発生状態を観察し、偏光板の長辺におけるずれ距離を測
定した。これら結果を表２に示す。With respect to this polarizing plate, foaming and peeling were observed in the same manner as in Example 1. In addition, the occurrence state of color unevenness was observed, and the displacement distance on the long side of the polarizing plate was measured. The results are shown in Table 2.
【００８４】[0084]
【比較例２】ポリマー溶液２とポリマー溶液９を固形分
比１００重量部／２５０重量部になるように混合し、こ
れに多官能性化合物として実施例３で使用したポリイソ
シアネート系化合物固形分０.０４重量部を添加し、よ
く撹拌して偏光板用粘着剤溶液を得た。Comparative Example 2 Polymer solution 2 and polymer solution 9 were mixed so that the solid content ratio was 100 parts by weight / 250 parts by weight, and the polyisocyanate-based compound used in Example 3 as a polyfunctional compound had a solid content of 0 parts. 0.04 parts by weight was added and well stirred to obtain a pressure-sensitive adhesive solution for a polarizing plate.
【００８５】なお多官能性化合物に対して反応性を有す
る官能基量の比率は、ポリマー溶液９／ポリマー溶液２
＝０重量％である。このようにして得られた偏光板用粘
着剤を用い、実施例１と同様にして粘着剤層を設けた偏
光板を調製した。The ratio of the amount of functional groups reactive with the polyfunctional compound is 9 polymer solution / 2 polymer solution.
= 0% by weight. Using the pressure-sensitive adhesive for polarizing plate thus obtained, a polarizing plate provided with a pressure-sensitive adhesive layer was prepared in the same manner as in Example 1.
【００８６】この偏光板について、実施例１と同様にし
て発泡、ハガレの発生状態を観察した。また、色むらの
発生状態を観察し、偏光板の長辺におけるずれ距離を測
定した。これら結果を表２に示す。With respect to this polarizing plate, the state of foaming and peeling was observed in the same manner as in Example 1. In addition, the occurrence state of color unevenness was observed, and the displacement distance on the long side of the polarizing plate was measured. The results are shown in Table 2.
【００８７】[0087]
【比較例３】ポリマー溶液１とポリマー溶液６を固形分
比１００重量部／１５０重量部になるように混合し、こ
れに多官能性化合物として実施例１で使用したエポキシ
系化合物固形分０.０２重量部を添加し、よく撹拌して
偏光板用粘着剤溶液を得た。Comparative Example 3 Polymer solution 1 and polymer solution 6 were mixed so that the solid content ratio was 100 parts by weight / 150 parts by weight, and the epoxy compound solid content used in Example 1 as a polyfunctional compound was 0.1. 02 parts by weight was added and well stirred to obtain an adhesive solution for a polarizing plate.
【００８８】なお多官能性化合物に対して反応性を有す
る官能基量の比率は、ポリマー溶液６／ポリマー溶液１
＝０重量％である。このようにして得られた偏光板用粘
着剤を用い、実施例１と同様にして粘着剤層を設けた偏
光板を調製した。The ratio of the amount of functional groups reactive with the polyfunctional compound is as follows: polymer solution 6 / polymer solution 1
= 0% by weight. Using the pressure-sensitive adhesive for polarizing plate thus obtained, a polarizing plate provided with a pressure-sensitive adhesive layer was prepared in the same manner as in Example 1.
【００８９】この偏光板について、実施例１と同様にし
て発泡、ハガレの発生状態を観察した。また、色むらの
発生状態を観察し、偏光板の長辺におけるずれ距離を測
定した。これら結果を表２に示す。With respect to this polarizing plate, foaming and peeling were observed in the same manner as in Example 1. In addition, the occurrence state of color unevenness was observed, and the displacement distance on the long side of the polarizing plate was measured. The results are shown in Table 2.
【００９０】[0090]
【比較例４】ポリマー溶液４とポリマー溶液５を固形分
比１００重量部／１５０重量部になるように混合し、こ
れに多官能性化合物として実施例１で使用したエポキシ
系化合物固形分０.０４重量部を添加し、よく撹拌して
偏光板用粘着剤溶液を得た。Comparative Example 4 Polymer solution 4 and polymer solution 5 were mixed so that the solid content ratio was 100 parts by weight / 150 parts by weight, and the epoxy compound solid content used in Example 1 as a polyfunctional compound was 0.1. 04 parts by weight was added and well stirred to obtain an adhesive solution for polarizing plate.
【００９１】なお多官能性化合物に対して反応性を有す
る官能基量の比率は、ポリマー溶液５／ポリマー溶液４
＝０重量％である。このようにして得られた偏光板用粘
着剤を用い、実施例１と同様にして粘着剤層を設けた偏
光板を調製した。The ratio of the amount of functional groups reactive with the polyfunctional compound is 5 polymer solution / 4 polymer solution.
= 0% by weight. Using the pressure-sensitive adhesive for polarizing plate thus obtained, a polarizing plate provided with a pressure-sensitive adhesive layer was prepared in the same manner as in Example 1.
【００９２】この偏光板について、実施例１と同様にし
て発泡、ハガレの発生状態を観察した。また、色むらの
発生状態を観察し、偏光板の長辺におけるずれ距離を測
定した。これら結果を表２に示す。With respect to this polarizing plate, foaming and peeling were observed in the same manner as in Example 1. In addition, the occurrence state of color unevenness was observed, and the displacement distance on the long side of the polarizing plate was measured. The results are shown in Table 2.
【００９３】[0093]
【比較例５】ポリマー溶液２とポリマー溶液７を固形分
比１００重量部／４０重量部になるように混合し、これ
に多官能性化合物として実施例２で使用したポリイソシ
アネート系化合物固形分１.０重量部を添加し、よく撹
拌して偏光板用粘着剤溶液を得た。Comparative Example 5 Polymer solution 2 and polymer solution 7 were mixed so that the solid content ratio was 100 parts by weight / 40 parts by weight, and the polyisocyanate-based compound solid content 1 used in Example 2 as a polyfunctional compound was mixed therein. 0.0 parts by weight was added and well stirred to obtain an adhesive solution for polarizing plate.
【００９４】なお多官能性化合物に対して反応性を有す
る官能基量の比率は、ポリマー溶液７／ポリマー溶液２
＝２０重量％である。このようにして得られた偏光板用
粘着剤を用い、実施例１と同様にして粘着剤層を設けた
偏光板を調製した。The ratio of the amount of the functional groups reactive with the polyfunctional compound is as follows: polymer solution 7 / polymer solution 2
= 20% by weight. Using the pressure-sensitive adhesive for polarizing plate thus obtained, a polarizing plate provided with a pressure-sensitive adhesive layer was prepared in the same manner as in Example 1.
【００９５】この偏光板について、実施例１と同様にし
て発泡、ハガレの発生状態を観察した。また、色むらの
発生状態を観察し、偏光板の長辺におけるずれ距離を測
定した。これら結果を表２に示す。With respect to this polarizing plate, foaming and peeling were observed in the same manner as in Example 1. In addition, the occurrence state of color unevenness was observed, and the displacement distance on the long side of the polarizing plate was measured. The results are shown in Table 2.
【００９６】[0096]
【比較例６】ポリマー溶液２とポリマー溶液８を固形分
比１００重量部／２０重量部になるように混合し、これ
に多官能性化合物として実施例２で使用したポリイソシ
アネート系化合物固形分１.０重量部を添加し、よく撹
拌して偏光板用粘着剤溶液を得た。Comparative Example 6 Polymer solution 2 and polymer solution 8 were mixed so that the solid content ratio was 100 parts by weight / 20 parts by weight, and the polyisocyanate compound solid content 1 used in Example 2 as a polyfunctional compound was mixed therein. 0.0 parts by weight was added and well stirred to obtain an adhesive solution for polarizing plate.
【００９７】なお多官能性化合物に対して反応性を有す
る官能基量の比率は、ポリマー溶液８／ポリマー溶液２
＝１００重量％である。このようにして得られた偏光板
用粘着剤を用い、実施例１と同様にして粘着剤層を設け
た偏光板を調製した。The ratio of the amount of functional groups reactive with the polyfunctional compound is 8 polymer solution / 2 polymer solution.
= 100% by weight. Using the pressure-sensitive adhesive for polarizing plate thus obtained, a polarizing plate provided with a pressure-sensitive adhesive layer was prepared in the same manner as in Example 1.
【００９８】この偏光板について、実施例１と同様にし
て発泡、ハガレの発生状態を観察した。また、色むらの
発生状態を観察し、偏光板の長辺におけるずれ距離を測
定した。これら結果を表２に示す。With respect to this polarizing plate, foaming and peeling were observed in the same manner as in Example 1. In addition, the occurrence state of color unevenness was observed, and the displacement distance on the long side of the polarizing plate was measured. The results are shown in Table 2.
【００９９】[0099]
【比較例７】ポリマー溶液２とポリマー溶液３を固形分
比１００重量部／１００重量部になるように混合し、こ
れに多官能性化合物として実施例３で使用したポリイソ
シアネート系化合物固形分０.０４重量部を添加し、よ
く撹拌して偏光板用粘着剤溶液を得た。Comparative Example 7 Polymer solution 2 and polymer solution 3 were mixed at a solid content ratio of 100 parts by weight / 100 parts by weight, and the polyisocyanate-based compound used in Example 3 as a polyfunctional compound had a solid content of 0. 0.04 parts by weight was added and well stirred to obtain a pressure-sensitive adhesive solution for a polarizing plate.
【０１００】なお多官能性化合物に対して反応性を有す
る官能基量の比率は、ポリマー溶液３／ポリマー溶液２
＝０重量％である。このようにして得られた偏光板用粘
着剤を用い、実施例１と同様にして粘着剤層を設けた偏
光板を調製した。The ratio of the amount of functional groups having reactivity with the polyfunctional compound is as follows: polymer solution 3 / polymer solution 2
= 0% by weight. Using the pressure-sensitive adhesive for polarizing plate thus obtained, a polarizing plate provided with a pressure-sensitive adhesive layer was prepared in the same manner as in Example 1.
【０１０１】この偏光板について、実施例１と同様にし
て発泡、ハガレの発生状態を観察した。また、色むらの
発生状態を観察し、偏光板の長辺におけるずれ距離を測
定した。これら結果を表２に示す。With respect to this polarizing plate, foaming and peeling were observed in the same manner as in Example 1. In addition, the occurrence state of color unevenness was observed, and the displacement distance on the long side of the polarizing plate was measured. The results are shown in Table 2.
【０１０２】[0102]
【比較例８】ポリマー溶液１の固形分１００重量部に多
官能性化合物として実施例１で使用したエポキシ系化合
物固形分０.０２重量部を添加し、よく撹拌して偏光板
用粘着剤溶液を得た。Comparative Example 8 To 100 parts by weight of the solid content of Polymer Solution 1, 0.02 parts by weight of the solid content of the epoxy compound used in Example 1 as a polyfunctional compound was added, and the mixture was well stirred to obtain a pressure-sensitive adhesive solution for a polarizing plate. Got
【０１０３】このようにして得られた偏光板用粘着剤を
用い、実施例１と同様にして粘着剤層を設けた偏光板を
調製した。この偏光板について、実施例１と同様にして
発泡、ハガレの発生状態を観察した。また、色むらの発
生状態を観察し、偏光板の長辺におけるずれ距離を測定
した。これら結果を表２に示す。Using the pressure-sensitive adhesive for polarizing plate thus obtained, a polarizing plate provided with a pressure-sensitive adhesive layer was prepared in the same manner as in Example 1. With respect to this polarizing plate, foaming and peeling were observed in the same manner as in Example 1. In addition, the occurrence state of color unevenness was observed, and the displacement distance on the long side of the polarizing plate was measured. The results are shown in Table 2.
【０１０４】なお、上記実施例および比較例におけるポ
リマー溶液の配合比率を表３に記載する。Table 3 shows the compounding ratios of the polymer solutions in the above Examples and Comparative Examples.
【０１０５】[0105]
【表１】 [Table 1]
【０１０６】[0106]
【表２】 [Table 2]
【０１０７】[0107]
【表３】 [Table 3]
───────────────────────────────────────────────────── フロントページの続き (56)参考文献 特開 昭60−207101（ＪＰ，Ａ) 特開 昭56−22371（ＪＰ，Ａ) 特開 平４−31480（ＪＰ，Ａ) 特開 昭61−47772（ＪＰ，Ａ) 特開 昭53−97851（ＪＰ，Ａ) 特許2549388（ＪＰ，Ｂ２) (58)調査した分野(Int.Cl.7，ＤＢ名) C09J 133/06 - 133/12 C09J 7/02 - 7/04 G02B 5/30 ─────────────────────────────────────────────────── ─── Continuation of the front page (56) Reference JP-A-60-207101 (JP, A) JP-A-56-22371 (JP, A) JP-A-4-31480 (JP, A) JP-A 61- 47772 (JP, A) JP-A-53-97851 (JP, A) Patent 2549388 (JP, B2) (58) Fields investigated (Int.Cl. 7 , DB name) C09J 133/06-133/12 C09J 7 / 02-7/04 G02B 5/30
Claims (4)
される繰返し単位を主繰返し単位とし、多官能性化合物
(C)に対して反応性を有する官能基含有モノマーから誘
導される繰返し単位が０.５〜２０重量％の量で共重合
すると共に重量平均分子量が１００万以上の高分子量
(メタ)アクリル系共重合体と、 該高分子量（メタ）アクリル系共重合体１００重量部に
対して、 (Ｂ) 多官能性化合物(C)に対して反応性を有する官能
基含有モノマーから誘導される繰返し単位が０〜１０重
量％の量で重合した重量平均分子量３万以下の低分子量
(メタ)アクリル系(共)重合体２０〜２００重量部と、 (Ｃ) 上記高分子量(メタ)アクリル系共重合体(A)およ
び／または低分子量（メタ）アクリル系（共）重合体
(B)と結合して架橋構造を形成可能な官能基を分子内中
に少なくとも２個有する多官能性化合物０.００５〜５
重量部とからなり、 該高分子量（メタ）アクリル系共重合体(A)および低分
子量（メタ）アクリル系（共）重合体(B)に共重合して
いる多官能性化合物(C)に対して反応性を有する官能基
含有モノマーから誘導される繰返し単位が、次式で表さ
れる官能基分配率で高分子量（メタ）アクリル系共重合
体(A)および低分子量（メタ）アクリル系（共）重合体
(B)に含有されることを特徴とする偏光板用粘着剤； 官能基分配率 ＝［低分子量(メタ)アクリル系共重合体
中における多官能性化合物(C)に対して反応性を有する
官能基含有モノマーから誘導される繰返し単位のモノマ
ー換算重量／高分子量(メタ)アクリル系共重合体中にお
ける多官能性化合物(C)に対して反応性を有する官能基
含有モノマーから誘導される繰返し単位のモノマー換算
重量］×１００＝０〜１５重量％。1. A polyfunctional compound comprising a repeating unit derived from (A) a (meth) acrylic acid ester as a main repeating unit.
A repeating unit derived from a functional group-containing monomer having reactivity with (C) is copolymerized in an amount of 0.5 to 20% by weight and has a high molecular weight of 1,000,000 or more.
A (meth) acrylic copolymer and (B) a functional group-containing monomer having reactivity with the polyfunctional compound (C) with respect to 100 parts by weight of the high molecular weight (meth) acrylic copolymer. Low molecular weight of weight average molecular weight of 30,000 or less polymerized in an amount of 0 to 10% by weight of the repeating unit to be derived.
20 to 200 parts by weight of a (meth) acrylic (co) polymer, and (C) the high molecular weight (meth) acrylic copolymer (A) and / or the low molecular weight (meth) acrylic (co) polymer
Multifunctional compound 0.005 to 5 having at least two functional groups capable of forming a crosslinked structure by bonding with (B)
And a polyfunctional compound (C) copolymerized with the high molecular weight (meth) acrylic copolymer (A) and the low molecular weight (meth) acrylic (co) polymer (B). Repeating units derived from a functional group-containing monomer that is reactive with the high molecular weight (meth) acrylic copolymer (A) and low molecular weight (meth) acrylic group have a functional group distribution ratio represented by the following formula. (Co) polymer
Adhesive for polarizing plate characterized by being contained in (B); functional group distribution ratio = [having reactivity with polyfunctional compound (C) in low molecular weight (meth) acrylic copolymer) Monomer equivalent weight of repeating units derived from functional group-containing monomer / repetition derived from functional group-containing monomer having reactivity with polyfunctional compound (C) in high molecular weight (meth) acrylic copolymer Monomer equivalent weight of unit] × 100 = 0 to 15% by weight.
(A)の重量平均分子量が１００万〜２００万の範囲内に
あり、かつ上記低分子量(メタ)アクリル系(共)重合体
(B)の重量平均分子量が１０００〜２００００の範囲内
にあることを特徴とする請求項第１項記載の偏光板用粘
着剤。2. The high molecular weight (meth) acrylic copolymer
The weight average molecular weight of (A) is in the range of 1 to 2,000,000 and the above low molecular weight (meth) acrylic (co) polymer
The pressure-sensitive adhesive for a polarizing plate according to claim 1, wherein the weight average molecular weight of (B) is in the range of 1,000 to 20,000.
される繰返し単位を主繰返し単位とし、多官能性化合物
(C)に対して反応性を有する官能基含有モノマーから誘
導される繰返し単位が０.５〜２０重量％の量で共重合
すると共に重量平均分子量が１００万以上の高分子量
(メタ)アクリル系共重合体と、 該高分子量（メタ）アクリル系共重合体１００重量部に
対して、 (Ｂ) 多官能性化合物(C)に対して反応性を有する官能
基含有モノマーから誘導される繰返し単位が０〜１０重
量％の量で重合した重量平均分子量３万以下の低分子量
(メタ)アクリル系(共)重合体２０〜２００重量部と、 (Ｃ) 上記高分子量(メタ)アクリル系共重合体(A)およ
び／または低分子量（メタ）アクリル系（共）重合体
(B)と結合して架橋構造を形成可能な官能基を分子内中
に少なくとも２個有する多官能性化合物０.００５〜５
重量部とからなり、 該高分子量（メタ）アクリル系共重合体(A)および低分
子量（メタ）アクリル系（共）重合体(B)に共重合して
いる多官能性化合物(C)に対して反応性を有する官能基
含有モノマーから誘導される繰返し単位が、次式で表さ
れる官能基分配率で高分子量（メタ）アクリル系共重合
体(A)および低分子量（メタ）アクリル系（共）重合体
(B)に含有されることを特徴とする粘着剤からなる粘着
剤層が、偏光板の少なくとも一方の面に形成されている
ことを特徴とする偏光板； 官能基分配率 ＝［低分子量(メタ)アクリル系共重合体
中における多官能性化合物(C)に対して反応性を有する
官能基含有モノマーから誘導される繰返し単位のモノマ
ー換算重量／高分子量(メタ)アクリル系共重合体中にお
ける多官能性化合物(C)に対して反応性を有する官能基
含有モノマーから誘導される繰返し単位のモノマー換算
重量］×１００＝０〜１５重量％。3. A polyfunctional compound comprising a repeating unit derived from (A) a (meth) acrylic acid ester as a main repeating unit.
A repeating unit derived from a functional group-containing monomer having reactivity with (C) is copolymerized in an amount of 0.5 to 20% by weight and has a high molecular weight of 1,000,000 or more.
A (meth) acrylic copolymer and (B) a functional group-containing monomer having reactivity with the polyfunctional compound (C) with respect to 100 parts by weight of the high molecular weight (meth) acrylic copolymer. Low molecular weight of weight average molecular weight of 30,000 or less polymerized in an amount of 0 to 10% by weight of the repeating unit to be derived.
20-200 parts by weight of a (meth) acrylic (co) polymer, and (C) the high molecular weight (meth) acrylic copolymer (A) and / or the low molecular weight (meth) acrylic (co) polymer
Multifunctional compound 0.005 to 5 having at least two functional groups capable of forming a crosslinked structure by bonding with (B)
And a polyfunctional compound (C) copolymerized with the high molecular weight (meth) acrylic copolymer (A) and the low molecular weight (meth) acrylic (co) polymer (B). Repeating units derived from a reactive functional group-containing monomer have a high molecular weight (meth) acrylic copolymer (A) and a low molecular weight (meth) acrylic type with a functional group distribution ratio represented by the following formula. (Co) polymer
A polarizing plate characterized in that an adhesive layer composed of the adhesive contained in (B) is formed on at least one surface of the polarizing plate; functional group distribution ratio = [low molecular weight ( In the (meth) acrylic copolymer, the monomer-equivalent weight of the repeating unit derived from the functional group-containing monomer reactive with the polyfunctional compound (C) in the (meth) acrylic copolymer / high molecular weight (meth) acrylic copolymer Monomer equivalent weight of repeating units derived from a functional group-containing monomer having reactivity with the polyfunctional compound (C)] × 100 = 0 to 15% by weight.
の重量平均分子量(A)が１００万〜２００万の範囲内に
あり、かつ上記低分子量(メタ)アクリル系(共)重合体
(B)の重量平均分子量が１０００〜２００００の範囲内
にあることを特徴とする請求項第３項記載の偏光板。4. The weight average molecular weight (A) of the high molecular weight (meth) acrylic copolymer is in the range of 1,000,000 to 2,000,000, and the low molecular weight (meth) acrylic (co) polymer is
The polarizing plate according to claim 3, wherein the weight average molecular weight of (B) is in the range of 1,000 to 20,000.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP09081197A JP3533589B2 (en) | 1997-04-09 | 1997-04-09 | Pressure-sensitive adhesive composition for polarizing plate and polarizing plate |
| KR1019970024155A KR100485626B1 (en) | 1997-04-09 | 1997-06-11 | Adhesive Composition for Polarizing Plates and Polarizing Plates |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP09081197A JP3533589B2 (en) | 1997-04-09 | 1997-04-09 | Pressure-sensitive adhesive composition for polarizing plate and polarizing plate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH10279907A JPH10279907A (en) | 1998-10-20 |
| JP3533589B2 true JP3533589B2 (en) | 2004-05-31 |
Family
ID=14008990
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP09081197A Expired - Fee Related JP3533589B2 (en) | 1997-04-09 | 1997-04-09 | Pressure-sensitive adhesive composition for polarizing plate and polarizing plate |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JP3533589B2 (en) |
| KR (1) | KR100485626B1 (en) |
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| JPS5397851A (en) * | 1977-02-07 | 1978-08-26 | Nitto Electric Ind Co | Light bending plate |
| JPS5622371A (en) * | 1979-07-31 | 1981-03-02 | Nitto Electric Ind Co Ltd | Water-dispersible pressure-sensitive adhesive |
| JPS60207101A (en) * | 1984-03-31 | 1985-10-18 | Sekisui Chem Co Ltd | Polarizing plate |
| JPS6147772A (en) * | 1984-08-15 | 1986-03-08 | Toagosei Chem Ind Co Ltd | Resin composition for pressure-sensitive adhesive |
| JP2549388B2 (en) * | 1987-09-08 | 1996-10-30 | 日東電工株式会社 | Pressure-sensitive adhesive polarizing plate |
| JPH0431480A (en) * | 1990-05-28 | 1992-02-03 | Soken Kagaku Kk | Acrylic pressure-sensitive adhesive composition |
-
1997
- 1997-04-09 JP JP09081197A patent/JP3533589B2/en not_active Expired - Fee Related
- 1997-06-11 KR KR1019970024155A patent/KR100485626B1/en not_active IP Right Cessation
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8962135B2 (en) | 2007-10-22 | 2015-02-24 | Nitto Denko Corporation | Pressure-sensitive adhesive composition for optical film, pressure-sensitive adhesive layer for optical film, production method thereof, pressure-sensitive adhesive optical film and image display |
| US7846542B2 (en) | 2008-02-15 | 2010-12-07 | Nitto Denko Corporation | Pressure-sensitive adhesive composition for optical films, pressure-sensitive adhesive optical film and image display |
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| US7862888B2 (en) | 2008-03-14 | 2011-01-04 | Nitto Denko Corporation | Pressure-sensitive adhesive composition for optical films, pressure-sensitive adhesive optical film and image display |
Also Published As
| Publication number | Publication date |
|---|---|
| KR100485626B1 (en) | 2006-01-12 |
| KR19980079266A (en) | 1998-11-25 |
| JPH10279907A (en) | 1998-10-20 |
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