JPH0795123B2 - Polarizing film - Google Patents
Polarizing filmInfo
- Publication number
- JPH0795123B2 JPH0795123B2 JP62028698A JP2869887A JPH0795123B2 JP H0795123 B2 JPH0795123 B2 JP H0795123B2 JP 62028698 A JP62028698 A JP 62028698A JP 2869887 A JP2869887 A JP 2869887A JP H0795123 B2 JPH0795123 B2 JP H0795123B2
- Authority
- JP
- Japan
- Prior art keywords
- film
- liquid crystalline
- polarizing film
- polarizing
- component
- 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
- 239000007788 liquid Substances 0.000 claims description 18
- 229920001634 Copolyester Polymers 0.000 claims description 15
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- 229920000728 polyester Polymers 0.000 claims description 7
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 6
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 6
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000000687 hydroquinonyl group Chemical class C1(O)=C(C=C(O)C=C1)* 0.000 claims description 3
- 229920006267 polyester film Polymers 0.000 claims description 2
- 150000003855 acyl compounds Chemical class 0.000 claims 1
- 239000000975 dye Substances 0.000 description 16
- 230000015572 biosynthetic process Effects 0.000 description 11
- 238000002834 transmittance Methods 0.000 description 8
- 238000000034 method Methods 0.000 description 7
- 238000002156 mixing Methods 0.000 description 6
- 230000010287 polarization Effects 0.000 description 6
- -1 vinyl halide Chemical class 0.000 description 5
- 229920000106 Liquid crystal polymer Polymers 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000004372 Polyvinyl alcohol Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229920002451 polyvinyl alcohol Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000005033 polyvinylidene chloride Substances 0.000 description 2
- XDUKPUDGTQCPFY-UHFFFAOYSA-N (2,5-dihydroxyphenyl) acetate Chemical class CC(=O)OC1=CC(O)=CC=C1O XDUKPUDGTQCPFY-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- SJEYSFABYSGQBG-UHFFFAOYSA-M Patent blue Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 SJEYSFABYSGQBG-UHFFFAOYSA-M 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000980 acid dye Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- MGIAHHJRDZCTHG-UHFFFAOYSA-N benzene-1,3-dicarboxylic acid;terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1.OC(=O)C1=CC=CC(C(O)=O)=C1 MGIAHHJRDZCTHG-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 1
- 239000000982 direct dye Substances 0.000 description 1
- 239000000986 disperse dye Substances 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920001600 hydrophobic polymer Polymers 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002074 melt spinning Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 150000004291 polyenes Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明は偏光フイルムに存する。詳しくは、サーモトロ
ピツク液晶性ポリエステルに二色性色素を染着配向させ
た偏光フイルムに関するもので、平行光線透過率に優
れ、かつ溶融製膜により簡便に製造することのできる偏
光フイルムに関する。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention resides in a polarizing film. More particularly, it relates to a polarizing film obtained by dyeing and orienting a dichroic dye on a thermotropic liquid crystalline polyester, which has excellent parallel light transmittance and can be easily produced by melt film formation.
従来の偏光フイルムとしては、ポリビニルアルコール
（PVA）系フイルムにヨウ素あるいは二色性染料を染着
したものが周知である。しかしながら、これらの偏光フ
イルムは偏光性能はすぐれているが、耐熱性、耐湿性な
どに難点があり、これを改良するために酢酸セルロース
系フイルムなどをラミネートして用いられている。しか
しながら、これでも用途によつては耐湿性が十分でな
い。As a conventional polarizing film, a polyvinyl alcohol (PVA) -based film dyed with iodine or a dichroic dye is well known. However, although these polarizing films have excellent polarization performance, they have drawbacks in heat resistance and moisture resistance, and in order to improve them, they are used by laminating a cellulose acetate film or the like. However, this still does not have sufficient moisture resistance depending on the application.
PVA系以外の疎水性重合体を基材とする偏光フイルムと
してポリ塩化ビニル（PVC）、ポリ塩化ビニリデン（PVD
C）などのハロゲン化ビニル系重合体を脱ハロゲン化水
素処理してポリエン構造を形成させた偏光フイルムも検
討されているが、これらも耐熱性および光、酸素に対す
る安定性に問題があるほか色相の自由な選択が不可能で
あることなどの理由から未だ偏光フイルムの主流を占め
るには至つていない。Polyvinyl chloride (PVC) and polyvinylidene chloride (PVD) as polarizing films based on hydrophobic polymers other than PVA
Polarizing films prepared by dehydrohalogenation treatment of vinyl halide polymers such as C) to form a polyene structure have also been investigated, but these also have problems in heat resistance and stability to light and oxygen, as well as hue. The mainstream of the polarizing film has not yet been dominated by the reason that it is impossible to freely select.
さらに例えば特開昭57−84409号公報、特開昭58−12462
1号公報などによればポリアミド系及びポリエステル系
偏光フイルムが示されている。ポリアミド−染料系及び
ポリエステル−染料系偏光フイルムは耐熱性、耐湿性、
力学的強度等はPVA−ヨウ素系偏光フイルム、PVA−二色
性染料系偏光フイルムにくらべてすぐれているが偏光性
能が２者にくらべて劣つているため未だ実用化の段階ま
で至つていない。Further, for example, JP-A-57-84409 and JP-A-58-12462.
According to Japanese Unexamined Patent Publication No. 1, etc., polyamide-based and polyester-based polarizing films are shown. Polyamide-dye-based and polyester-dye-based polarizing films have heat resistance, moisture resistance,
Mechanical strength such as PV A - Itaritsu to the stage of yet practical because is excellent as compared with the dichroic dye-containing polarizing film is the polarizing performance is Retsutsu than the two parties - iodine polarizing film, PV A Not not.
本発明者等は上述のような従来の問題点を解消すべく鋭
意検討を行なつた結果、特定のサーモトロピツク液晶性
ポリエステルと二色性色素を組合せて用いれば、溶融製
膜という簡単な方法で高度な偏光性能を発揮し、しかも
透明性の良好なフイルムとなることを見いだし、本発明
を完成した。The present inventors have conducted extensive studies to solve the above conventional problems, and as a result, if a specific thermotropic liquid crystalline polyester and a dichroic dye are used in combination, it is easy to perform melt film formation. The present invention has been completed by finding that the film can exhibit a high polarization performance by the method and has a good transparency.
即ち、本発明の要旨は、二色性色素が染着配向されたサ
ーモトロピツク液晶性ポリエステルフイルムからなる偏
光フイルムであつて、サーモトロピツク液晶性ポリエス
テルがハイドロキノン誘導体成分（Ａ）、テレフタル酸
成分（Ｂ）、イソフタル酸成分（Ｃ）及びパラヒドロキ
シ安息香酸成分（Ｄ）からなる共重合ポリエステルであ
る偏光フイルムに存する。That is, the gist of the present invention is a polarizing film comprising a thermotropic liquid crystalline polyester film in which a dichroic dye is dyed and oriented, wherein the thermotropic liquid crystalline polyester is a hydroquinone derivative component (A) or a terephthalic acid component. It exists in a polarizing film which is a copolyester composed of (B), an isophthalic acid component (C) and a parahydroxybenzoic acid component (D).
（Ａ）成分のハイドロキノン誘導体成分は、下記一般式
（Ｉ）又は（II）で示される化合物、あるいはこれらの
アシル化物から得られる成分である。The hydroquinone derivative component as the component (A) is a component obtained from a compound represented by the following general formula (I) or (II), or an acylated product thereof.
（（Ｉ）、（II）式中、Ｘ、Ｘ′は同一又は異なつてい
てもよく、炭素数１〜８のアルキル基または の基を表わす。） ここで、炭素数１〜８のアルキル基としては直鎖又は分
岐状のアルキル基であつて、例えばメチル基、エチル
基、プロピル基、イソプロピル基、ブチル基、イソブチ
ル基sec−ブチル基、tert−ブチル基、ペンチル基、1,1
−ジメチルブチル基、1,1−ジメチル−3,3−ジメチルブ
チル基、アミル基、ヘキシル基等が挙げられる。 (In the formulas ((I) and (II), X and X'may be the same or different, and may be an alkyl group having 1 to 8 carbon atoms or Represents the base of. Here, the alkyl group having 1 to 8 carbon atoms is a linear or branched alkyl group, for example, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group sec-butyl group, tert. -Butyl group, pentyl group, 1,1
-Dimethylbutyl group, 1,1-dimethyl-3,3-dimethylbutyl group, amyl group, hexyl group and the like.
また、 基を有する化合物、例べば、 3,4,5,6−ジベンゾ−1,2−オキサホスフアン−２−オキ
シドをハイドロキノンと反応させることにより得られ
る。Also, A compound having a group, for example, Obtained by reacting 3,4,5,6-dibenzo-1,2-oxaphosphane-2-oxide with hydroquinone.
本発明の共重合ポリエステルを製造するには、例えば、
アセトキシハイドロキノン誘導体、パラアセトキシ安息
香酸、テレフタル酸及びイソフタル酸の各成分を仕込
み、275℃に昇温し２時間撹拌後、減圧下（0.3mmHg）で
５〜８時間重合すればよい。To produce the copolyester of the present invention, for example,
The acetoxyhydroquinone derivative, paraacetoxybenzoic acid, terephthalic acid, and isophthalic acid are charged, the temperature is raised to 275 ° C., the mixture is stirred for 2 hours, and then the mixture is polymerized under reduced pressure (0.3 mmHg) for 5 to 8 hours.
このサーモトロピツク液晶性共重合ポリエステルは、剪
断及びドラフト下で溶融製膜することにより、高配向
で、しかも非常に透明性の優れたフイルムとすることが
できる。This thermotropic liquid crystalline copolyester can be formed into a highly oriented film with excellent transparency by melt-forming under shear and draft.
溶液状態あるいは溶融状態で液晶性を示す高分子化合物
（液晶性ポリマー）の高配向性は溶液あるいは溶融紡糸
又は製膜により加工して高弾性を有する繊維、フイルム
とする技術として知られているが、液晶性ポリマーの不
均一性や液晶相の回位などにより得られる繊維、フイル
ムは不透明なものであり、偏光フイルムなどの光学的用
途への応用は不可能であつた。The high orientation of a polymer compound (liquid crystalline polymer) that exhibits liquid crystallinity in a solution state or a molten state is known as a technology for producing a fiber or film having high elasticity by processing by solution or melt spinning or film formation. The fibers and films obtained by the non-uniformity of the liquid crystalline polymer and the rotation of the liquid crystal phase are opaque and cannot be applied to optical applications such as polarizing films.
以上のように本発明によりサーモトロピツク液晶性共重
合ポリエステルフイルムに透明性が付与され、かつ該フ
イルムの高配向性を利用し二色性色素を染着配向させ、
偏光フイルムとした事は非常に画期的な事である。As described above, according to the present invention, the thermotropic liquid crystalline copolyester film is provided with transparency, and the dichroic dye is dyed and oriented by utilizing the high orientation of the film,
Having a polarizing film is a very epoch-making thing.
上記の液晶性共重合ポリエステル樹脂から偏光フイルム
を製造するには該樹脂に二色性色素を混合した後溶融製
膜される。In order to produce a polarizing film from the above-mentioned liquid crystalline copolyester resin, a dichroic dye is mixed with the resin and then the film is melted.
本発明に使用される二色性色素は、その分子構造上二色
性を有する直接染料、分散染料、酸性染料などの中から
選ばれ、その一例を挙げれば次のような構造式を有する
ものである。The dichroic dye used in the present invention is selected from direct dyes, disperse dyes, acid dyes and the like having a dichroism in its molecular structure, and examples thereof include those having the following structural formulas. Is.
二色性色素は、上記したようなものを一種類あるいは数
種類の混合物として用いれば良い。使用方法は、例えば
サーモトロピツク液晶性共重合ポリエステルとドライブ
レンド、溶融ブレンド、溶媒混合等の方法で混合して用
いる。二色性色素の混合量としては0.01重量％以上10重
量％未満の間から選ばれるのが好ましい。 As the dichroic dye, the above-mentioned ones may be used alone or as a mixture of several kinds. As for the method of use, for example, they are mixed with the thermotropic liquid crystalline copolymer polyester by a method such as dry blending, melt blending, solvent mixing and the like. The mixing amount of the dichroic dye is preferably selected from 0.01% by weight or more and less than 10% by weight.
本発明に用いるサーモトロピツク液晶性共重合ポリエス
テルの特徴は溶融製膜という非常に簡単な工程のみで高
配向性能を発起し、製膜時二色性色素をブレンドするこ
とにより容易に偏光フイルムを製造できることである。
このことは通常のポリマーの場合、配向フイルムを得よ
うとすると製膜後なんらかの延伸処理を施す必要がある
事に比較すると、製造コスト面で大きな長所であり、又
溶融製膜工程のみで偏光フイルムを製造する方法は新規
なものである。The feature of the thermotropic liquid crystalline copolyester used in the present invention is that the high orientation performance is generated only by a very simple process of melt film formation, and a polarizing film can be easily formed by blending a dichroic dye during film formation. It is possible to manufacture.
This is a great advantage in terms of production cost compared to the fact that in the case of ordinary polymers, it is necessary to perform some stretching treatment after film formation in order to obtain an oriented film, and the polarizing film can be formed only by the melt film formation process. The method of manufacturing is a novel one.
溶融製膜は通常矩形、円形のダイスを用いて適当な剪断
及びドラフト条件下にて成形される。Melt film formation is usually performed using a rectangular or circular die under appropriate shear and draft conditions.
本発明におけるサーモトロピツク液晶性共重合ポリエス
テルを剪断下で製膜すると樹脂セグメントの剛直性によ
り流れ方向にセグメントが配向し、その結果としてフイ
ルムに透明感が付与される。When the thermotropic liquid crystalline copolyester of the present invention is formed into a film under shearing, the rigidity of the resin segment causes the segments to be oriented in the flow direction, and as a result, the film is given a sense of transparency.
製膜温度は本発明のサーモトロピツク液晶性共重合ポリ
エステルが液晶性（溶融時異方性）を示す温度範囲であ
ればよく、通常230℃〜400℃の範囲で行なわれる。The film-forming temperature may be in the temperature range in which the thermotropic liquid crystalline copolyester of the present invention exhibits liquid crystallinity (anisotropic property during melting), and is usually in the range of 230 ° C to 400 ° C.
以上のようにして得られた偏光フイルムはサーモトロピ
ツク液晶性共重合ポリエステルを素材としており、しか
も、液晶性共重合ポリエステルを用いたフイルムとして
は画期的な透明性を有しているという点で全く新規なも
のであり、該共重合ポリエステルフイルムはそれ自体で
すぐれた力学的性質、耐熱、耐水、耐候性を有し、これ
よりなる偏光フイルムは高温、高湿度の条件下において
偏光性能の低下を起こさない。The polarizing film obtained as described above is made of a thermotropic liquid crystalline copolyester as a material, and has a epoch-making transparency as a film using the liquid crystalline copolyester. The copolyester film itself has excellent mechanical properties, heat resistance, water resistance, and weather resistance, and a polarizing film made of this has a high polarization performance under high temperature and high humidity conditions. Does not cause a drop.
又、使用目的によつては他のプラスチツクとのラミネー
シヨンや共押出し等により偏光フイルムを保護した状態
で使用してもよく、さらには偏光フイルム自体、あるい
は保護層を介して、表面に蒸着、スパツタリングまたは
塗布法によりインジウム−スズ系酸化物等の透明導電性
膜を形成して実用に供する。Also, depending on the purpose of use, it may be used in a state in which the polarizing film is protected by lamination or coextrusion with other plastics, and further, the polarizing film itself, or via a protective layer, vapor deposition on the surface, A transparent conductive film such as an indium-tin oxide is formed by sputtering or a coating method and put to practical use.
以下実施例を挙げて本発明を説明するが本発明はその要
旨を越えない限り以下の実施例に限定されるものではな
い。The present invention will be described below with reference to examples, but the present invention is not limited to the following examples as long as the gist thereof is not exceeded.
実施例に先だつて下記項目の測定法について記載する。Prior to the examples, the measuring methods of the following items will be described.
平行光線透過率…… 積分球式光線透過率測定装置 テジタル濁度計NDH−20D（日本電色工業株式会社製）を
用いたJIS K6714に準じた。Parallel light transmittance ... In accordance with JIS K6714 using an integrating sphere light transmittance measuring device Digital Turbidity Meter NDH-20D (Nippon Denshoku Industries Co., Ltd.).
Fdye値…… 分光光度計228形（日立製作所製）を用いて入射光線の
偏光面と配向軸が垂直、平行の場合の透過率II、IIIを
可視領域において測定し、次式に基づく配向係数（Fdy
e）を算出した。Fdye value …… Measures the transmittances I I and I II in the visible region when the polarization plane of the incident light is perpendicular to and parallel to the orientation axis using a spectrophotometer type 228 (manufactured by Hitachi, Ltd.) and is based on the following formula Orientation factor (Fdy
e) was calculated.
Fdye＝（Ｄ−１）／（Ｄ＋２） （但し、Ｄは吸収二色比であり、 Ｄ＝Log（I0/III）/Log（I0/II） I0は同一延伸処理条件の無染色フイルムの透過率であ
る） Fdye値は二色性色素の配向度を表わし、Fdye値が大なる
ことは偏光フイルムの偏光性能が大なることを示す。Fdye = (D-1) / (D + 2) (where D is the absorption dichroic ratio, and D = Log (I 0 / I II ) / Log (I 0 / I I ) I 0 is the same drawing treatment condition. The Fdye value, which is the transmittance of the undyed film, represents the degree of orientation of the dichroic dye, and a large Fdye value indicates that the polarization performance of the polarizing film is large.
実施例１ ハイドロキノン誘導体 テレフタル酸 イソフタル酸 及びパラヒドロキシ安息香酸 を、5/5/3/2のモル比で共重合した高分子化合物をＴダ
イ（ダイ幅120mm;リツプクリアランス0.2mm）を備えた3
0mmφ押出機を用いて、温度340℃、剪断速度500sec-1、
ドラフト比10の条件で製膜した。この時得られた無染色
フイルムは透明で、その平行光線透過率はフイルム厚25
μｍで87％を示した。又上記高分子化合物をヒートステ
ージを装着した偏光顕微鏡下で観察し、340℃で溶融時
異方性を示すことを確認した。Example 1 Hydroquinone derivative Terephthalic acid Isophthalic acid And para-hydroxybenzoic acid 3) equipped with T-die (die width 120 mm; lip clearance 0.2 mm)
Using a 0 mmφ extruder, temperature 340 ℃, shear rate 500 sec -1 ,
The film was formed under the condition that the draft ratio was 10. The undyed film obtained at this time is transparent, and its parallel light transmittance is 25 mm.
It showed 87% in μm. Further, the above polymer compound was observed under a polarizing microscope equipped with a heat stage, and it was confirmed that it exhibited anisotropy when melted at 340 ° C.
次に上記サーモトロピツク液晶性高分子化合物に下記式
で示される色素を ヘンシエルミキサーで0.5重量％の割合に混合したのち
上記と同様の方法でＴダイ製膜を行なう青色の偏光フイ
ルムを製造した。得られた偏光フイルムのFdye値は0.75
であつた。Next, a dye represented by the following formula is added to the thermotropic liquid crystalline polymer compound. A blue polarizing film was produced by mixing in a Hensiel mixer at a ratio of 0.5% by weight and then performing T-die film formation in the same manner as above. The obtained polarizing film has an Fdye value of 0.75
It was.
比較例１ ポリエチレンテレフタレート成分が50モル％、パラヒド
ロキシ安息香酸成分が50モル％である共重合ポリエステ
ルをドラフト比を15、温度を275℃とした以外は実施例
１と全く同様の製膜を行なつた。得られた無染色フイル
ムの平行光線透過率はフイルム厚15μｍで30％と不透明
なものであつた。又、この共重合ポリエステルをヒート
ステージを装着した偏光顕微鏡下で観察したところ275
℃で溶融異方性を示し、該共重合ポリエステルもサーモ
トロピツク液晶性高分子化合物であることを確認した。Comparative Example 1 Except for using a copolyester having a polyethylene terephthalate component of 50 mol% and a parahydroxybenzoic acid component of 50 mol% in a draft ratio of 15 and a temperature of 275 ° C., the same film formation as in Example 1 was performed. Natsuta. The parallel light transmittance of the resulting undyed film was opaque, 30% at a film thickness of 15 μm. In addition, when this copolyester was observed under a polarizing microscope equipped with a heat stage, 275
Melting anisotropy was exhibited at ° C, and it was confirmed that the copolymerized polyester was also a thermotropic liquid crystalline polymer compound.
次に実施例１と同一の色素を実施例１と同様の方法で混
合した後上記と同様の方法でＴダイ製膜を行なつたがFd
ye値は0.42と配向性も低いフイルムであつた。Next, the same dye as in Example 1 was mixed in the same manner as in Example 1, and then T-die film formation was performed in the same manner as above.
The ye value was 0.42, and the film had low orientation.
以上のように本発明のサーモトロピツク液晶性共重合ポ
リエステルは無染色時のフイルムは平行光線透過率が80
％以上と高く、またこれを用いた偏光フイルムも透明性
が良好で配向係数Fdye値が0.5以上と高く偏光能が大き
いことがわかる。As described above, the thermotropic liquid crystalline copolyester of the present invention has a parallel light transmittance of 80 when the film is not dyed.
%, The polarizing film using the same has good transparency and the orientation coefficient Fdye value is 0.5 or more, and the polarizing ability is high.
本発明によれば簡便な方法で、透明性、偏光性能等に優
れたフイルムを得ることができ、実用上大変効果的であ
る。According to the present invention, a film having excellent transparency and polarization performance can be obtained by a simple method, which is very effective in practice.
Claims (2)
ック液晶性ポリエステルフィルムからなる偏光フィルム
であって、サーモトロピック液晶性ポリエステルが下記
一般式（Ｉ）又は（II）で示される化合物、あるいはこ
れらのアシル化物から形成されるハイドロキノン誘導体
成分（Ａ）、テレフタル酸成分（Ｂ）、イソフタル酸成
分（Ｃ）及びパラヒドロキシ安息香酸成分（Ｄ）からな
る共重合ポリエステルであることを特徴とする偏光フィ
ルム。 （（Ｉ）、（II）式中、Ｘ、Ｘ′は同一又は異なつてい
てもよく、炭素数１〜８のアルキル基又は 1. A polarizing film comprising a thermotropic liquid crystalline polyester film in which a dichroic dye is dyed and oriented, wherein the thermotropic liquid crystalline polyester is a compound represented by the following general formula (I) or (II): Alternatively, it is a copolyester comprising a hydroquinone derivative component (A), a terephthalic acid component (B), an isophthalic acid component (C) and a parahydroxybenzoic acid component (D) formed from these acyl compounds. Polarizing film. (In the formulas ((I) and (II), X and X ′ may be the same or different, and may be an alkyl group having 1 to 8 carbon atoms or
般式（III）で示される化合物、あるいはこれらのアシ
ル化物から形成される成分であることを特徴とする特許
請求範囲第１項に記載の偏光フィルム。 2. The polarized light according to claim 1, wherein the hydroquinone derivative component (A) is a compound represented by the following general formula (III) or a component formed from an acylated product thereof. the film.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62028698A JPH0795123B2 (en) | 1987-02-10 | 1987-02-10 | Polarizing film |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62028698A JPH0795123B2 (en) | 1987-02-10 | 1987-02-10 | Polarizing film |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63195602A JPS63195602A (en) | 1988-08-12 |
| JPH0795123B2 true JPH0795123B2 (en) | 1995-10-11 |
Family
ID=12255691
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62028698A Expired - Fee Related JPH0795123B2 (en) | 1987-02-10 | 1987-02-10 | Polarizing film |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0795123B2 (en) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2620815B2 (en) * | 1990-07-18 | 1997-06-18 | ヘキストジャパン株式会社 | Liquid crystal display device |
| US5667719A (en) * | 1995-06-02 | 1997-09-16 | Hoechst Celanese Corp. | High extinction polarizer films comprising liquid crystal polymeric moieties |
| US5753145A (en) * | 1995-06-02 | 1998-05-19 | Hoecst Celanese Corp. | Polarizer films with high thermal and hygroscopic stability |
| US5707566A (en) * | 1995-06-02 | 1998-01-13 | Hoechst Celanese Corp. | Process for preparing high performance polarizer films |
| US5672296A (en) * | 1995-06-02 | 1997-09-30 | Hoechst Celanese Corp. | Polarizer films comprising wholly aromatic liquid crystalline polymers and dichroic dyes |
| US5746949A (en) * | 1995-11-21 | 1998-05-05 | Hoechst Celanese Corp. | Polarizer films comprising aromatic liquid crystalline polymers comprising dichroic dyes in their main chains |
| US5738803A (en) * | 1995-12-14 | 1998-04-14 | Hoechst Celanese Corp | Polarizer films comprising wholly aromatic liquid crystalline polymers and dichroic dyes |
| US5738918A (en) * | 1996-06-14 | 1998-04-14 | Hoechst Celanese Corp | Laminates of liquid crystalline polymeric films for polarizer applications |
| US5863622A (en) * | 1996-12-05 | 1999-01-26 | Hoechst Celanese Corporation | Polarizer laminates comprising coextruded liquid crystal polymer moieties and integral thermoplastic cover layers |
| US5851423A (en) * | 1997-05-22 | 1998-12-22 | Hoechst Celanese Corporation | Liquid crystal display devices incorporating polarizers comprising liquid crystal polymers |
| US6312772B1 (en) | 1997-10-20 | 2001-11-06 | Hoechst Celanese Corporation | Multilayer laminate formed from a substantially stretched non-molten wholly aromatic liquid crystalline polymer and non-polyester thermoplastic polymer |
| US6268026B1 (en) | 1997-10-20 | 2001-07-31 | Hoechst Celanese Corporation | Multilayer laminate formed from a substantially stretched non-molten wholly aromatic liquid crystalline polymer and non-liquid crystalline polyester and method for forming same |
| US6426128B1 (en) | 1998-01-06 | 2002-07-30 | Hna Holdings, Inc. | Co-processable multi-layer laminates for forming high strength, haze-free, transparent articles and methods of producing same |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55123425A (en) * | 1979-03-19 | 1980-09-22 | Teijin Ltd | Preparation of polyester film |
| JPS60218602A (en) * | 1984-04-16 | 1985-11-01 | Mitsui Toatsu Chem Inc | polarizing film |
| JPS6197326A (en) * | 1984-10-18 | 1986-05-15 | Unitika Ltd | Production of liquid crystal polyster |
-
1987
- 1987-02-10 JP JP62028698A patent/JPH0795123B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPS63195602A (en) | 1988-08-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR100554582B1 (en) | Modified Copolyester and Improved Multilayer Reflective Film | |
| JP5048505B2 (en) | Modified copolyester and optical film comprising modified copolyester | |
| KR100648552B1 (en) | Multilayer optics | |
| JPH0795123B2 (en) | Polarizing film | |
| KR20020035654A (en) | Optical Bodies Made With a Birefringent Polymer | |
| JP2002509282A (en) | Optical device including dichroic polarizer and multilayer optical film | |
| JPWO2001009649A1 (en) | Retardation film, retardation film composite, and liquid crystal display device using the same | |
| JP2710630B2 (en) | Polarizing film and method for producing the same | |
| JPH0652327B2 (en) | Polarizing film | |
| JPH0686594B2 (en) | Process for producing monodomain cholesteric liquid crystalline polyester film or sheet | |
| JP2017052824A (en) | Copolyester resin and UV cut film | |
| KR20090113368A (en) | Cellulose ester film and its manufacturing method | |
| JPH0470603B2 (en) | ||
| JP2008052170A (en) | Polarization film, method for manufacturing polarization film, and polarization plate and liquid crystal using the same | |
| JPS62270664A (en) | Quinophthalone dye and polarizing film obtained by using same | |
| JPS61285259A (en) | Dichroic dye and polarizing film containing same | |
| CN101819292B (en) | Retardation film, use of said retardation film, and novel modified polymer | |
| JPS62204202A (en) | Polarizing film | |
| JPH083564B2 (en) | Polarizing film | |
| JP5146252B2 (en) | Polarizing film, manufacturing method of polarizing film, and liquid crystal display device using the same | |
| JP3428295B2 (en) | Polarizing plate protective film and polarizing plate | |
| JPS6233931B2 (en) | ||
| JPS60125804A (en) | Polarizing film | |
| JPS5926471B2 (en) | laminate | |
| CN100579993C (en) | Retardation film, use thereof, and novel modified polymer |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |