JPS63195602A - Polarizing film - Google Patents
Polarizing filmInfo
- Publication number
- JPS63195602A JPS63195602A JP2869887A JP2869887A JPS63195602A JP S63195602 A JPS63195602 A JP S63195602A JP 2869887 A JP2869887 A JP 2869887A JP 2869887 A JP2869887 A JP 2869887A JP S63195602 A JPS63195602 A JP S63195602A
- Authority
- JP
- Japan
- Prior art keywords
- component
- film
- polarizing
- polarizing film
- polyester
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000007788 liquid Substances 0.000 claims abstract description 22
- 229920000728 polyester Polymers 0.000 claims abstract description 18
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims abstract description 10
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims abstract description 10
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 229920006267 polyester film Polymers 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims 3
- 125000000687 hydroquinonyl group Chemical class C1(O)=C(C=C(O)C=C1)* 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 15
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 abstract description 10
- 238000002156 mixing Methods 0.000 abstract description 6
- 239000004974 Thermotropic liquid crystal Substances 0.000 abstract description 2
- 229920001577 copolymer Polymers 0.000 abstract description 2
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- 239000000155 melt Substances 0.000 abstract 1
- 239000000975 dye Substances 0.000 description 20
- 229920001634 Copolyester Polymers 0.000 description 10
- 238000002834 transmittance Methods 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 5
- 229920000106 Liquid crystal polymer Polymers 0.000 description 3
- 239000004372 Polyvinyl alcohol Substances 0.000 description 3
- 239000004020 conductor Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 230000010287 polarization Effects 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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 239000004800 polyvinyl chloride Substances 0.000 description 2
- 229920000915 polyvinyl chloride Polymers 0.000 description 2
- 238000010008 shearing Methods 0.000 description 2
- -1 vinyl halide Chemical class 0.000 description 2
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 1
- XDUKPUDGTQCPFY-UHFFFAOYSA-N (2,5-dihydroxyphenyl) acetate Chemical compound 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
- 229940126657 Compound 17 Drugs 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
- 229920001328 Polyvinylidene chloride Polymers 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
- 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
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 239000000982 direct dye Substances 0.000 description 1
- 239000000986 disperse dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 210000004177 elastic tissue Anatomy 0.000 description 1
- 210000003038 endothelium Anatomy 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 239000000835 fiber Substances 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
- 238000003475 lamination Methods 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000002074 melt spinning Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 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
- 239000005033 polyvinylidene 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
- 239000002904 solvent Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000003756 stirring 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
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は偏光フィルムに存する。詳しくは、サーモトロ
ピック液晶性ポリエステルに二色性色素を染着配向させ
た偏光フィルムに関するもので、平行光線透過率に優れ
、かつ必融裂膜により簡便に製造することのできる偏光
フィルムに関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention resides in a polarizing film. More specifically, the present invention relates to a polarizing film in which a dichroic dye is dyed and oriented to a thermotropic liquid crystalline polyester, which has excellent parallel light transmittance, and which can be easily manufactured using a fusing film.
従来の偏光フィルムとしては、ポリビニルアルコール（
ＰＶＡ）系フィ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
ィ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
系フィルムなどをラミネートして用いられている。Conventional polarizing films include polyvinyl alcohol (
PVA) type films dyed with iodine or dichroic dyes are well known. However, although these polarizing films have excellent polarizing performance, they have drawbacks in heat resistance, moisture resistance, etc., and in order to improve these problems, they are laminated with a cellulose acetate film or the like.
しかしながら、これでも用途によっては耐湿性が十分で
ない。However, even this does not provide 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ィルム
としてポリ塩化ビニル（ＰＶＯ）、ポリ塩化ビニリデン
（ＰＶＤＯＪ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°ポリエン構造な形成させた偏光フ
ィ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ィルムの
主流を占めるには至っていない。As a polarizing film based on hydrophobic polymers other than PVA, vinyl halide polymers such as polyvinyl chloride (PVO) and polyvinylidene chloride (PVDOJ) are dehydrohalogenated to form a polyene structure. Polarizing films are also being considered, but these also have poor heat resistance and light resistance.
It has not yet become the mainstream of polarizing films because of its stability against oxygen and the inability to freely select hues.
さらに例えば特開昭！ｒ７−４’ｌ’１０９号公報、特
開昭５ｇ−／４４Ｉ４コ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ィルムが示されている。Furthermore, for example, Tokukai Akira! Polyamide-based and polyester-based polarizing films are disclosed in R7-4'l'109, JP-A-5G-/44I4-1, and the like.
ポリアミド−染料系及びポリエステル−染料系偏光フィ
ルムは耐熱性、耐湿性、力学的強度等はＰＴＡ−ヨウ素
系偏光フィルム、ＰｖＡ−二色性染料系偏光フィルムに
くらべてすぐれているが偏光性能がコ者にくらべて劣っ
ているため未だ実用化の段階まで至っていない。Polyamide-dye-based and polyester-dye-based polarizing films have better heat resistance, moisture resistance, mechanical strength, etc. than PTA-iodine-based polarizing films and PvA-dichroic dye-based polarizing films, but their polarizing performance is inferior. However, it has not yet reached the stage of practical use because it is inferior to those of other researchers.
本発明省等は上述のような従来の問題点を解消するべく
鋭意検討を行なった結果、特定のサーモトロピック液晶
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
も透明性の良効なフィルムとなることを見いだし、本発
明を完成した。The Ministry of the Invention and others conducted intensive studies to solve the above-mentioned conventional problems, and found that if a specific thermotropic liquid crystalline polyester and dichroic dye are used in combination, it can be made by a simple method of melt film formation. The present invention was completed by discovering that the film exhibits high polarization performance and is highly transparent.
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
テルがハイドロキノン肪導体成分（Ａ）、テレフタル酸
成分（Ｅ）、イソフタル酸成分（ＯＪ及びパラヒドロキ
シ安息香酸成分（ＤＪからなる共重合ポリエステルで（
Ａ）対（Ｄ）の組成比がモル％で３対９５からり０対Ｊ
Ｏかつ、（Ｂ）対（Ｃ）の組成比がモル％で５θ対ＳＯ
から１００対θの間である偏光フィルムに存する。That is, the gist of the present invention is a polarizing film made of a thermotropic liquid crystalline polyester film in which a dichroic dye is dyed and oriented, the thermotropic liquid crystalline polyester containing a hydroquinone fatty conductor component (A), a terephthalic acid component ( E), a copolymerized polyester consisting of an isophthalic acid component (OJ) and a para-hydroxybenzoic acid component (DJ).
The composition ratio of A) to (D) is 3 to 95 in mol% and 0 to J
O and the composition ratio of (B) to (C) is 5θ to SO in mol%
and 100 to θ.
本発明の偏光フィルムを得るためのサーモトロピック液
晶性ポリエステルはハイドロキノンＭｉ体成分（Ａ）、
テレフタル酸成分（Ｂ）、イソフタル酸成分ＣＯ）及び
パラヒドロキシ安息香酸成分（ＤＪからなる共重合ポリ
エステルで（Ａ）対（ＤＪの組成比がモル％でＳ対９！
から７０対３０かつ、（Ｂ）対（Ｃ）の組成比がモル％
でＳＯ対ＳＯから１００対０の間であるサーモトロピッ
ク液晶性共重合ポリエステルである。The thermotropic liquid crystalline polyester for obtaining the polarizing film of the present invention includes hydroquinone Mi component (A),
A copolymerized polyester consisting of a terephthalic acid component (B), an isophthalic acid component CO), and a para-hydroxybenzoic acid component (DJ, where the composition ratio of DJ is S to 9!
70:30 and the composition ratio of (B) to (C) is mol%
It is a thermotropic liquid crystalline copolyester having a ratio of SO to SO to 100 to 0.
（Ａ）対（Ｄ）の組成比において、上記範囲よりも（Ａ
）成分が多くなると配向性が阻害され、（Ｄ）成分が多
（なると結晶化が促進されるために透明性が阻害される
。In the composition ratio of (A) to (D), (A)
If the amount of component (D) increases, the orientation will be inhibited, and if the component (D) increases, crystallization will be promoted and transparency will be inhibited.
（Ｂ）対（Ｃ）の組成比において、上記範囲よりも（Ｃ
）成分が多くなると配向性が阻害される。In the composition ratio of (B) to (C), (C
) When the amount of the component increases, the orientation is inhibited.
（Ａ）成分のハイドロキノン肪導体成分は、好ましくは
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 fatty conductor component (A) is preferably a compound represented by the following general formula (I) or (II), or a component obtained from an acylated product thereof.
λ′
（（１）、（ＩＩ）式中、Ｘ、Ｘ’は同−又は異なって
いてもよく、炭素数／ −ｆｆのアルキル基またはここ
で、炭素数ｌ−ざのアルキル基としては直鎖又は分岐状
のアルキル基であって、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、
５ｅＣ−ブチル基、ｔａｒｔ−ブチル基、ペンチル基、
／、 ／−ジメチルブチル基、／、 ／−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
げもれる。λ' (In formulas (1) and (II), X and X' may be the same or different, and as an alkyl group with carbon number/-ff or an alkyl group with carbon number l-ff, A chain or branched alkyl group, such as a methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group,
5eC-butyl group, tart-butyl group, pentyl group,
/, /-dimethylbutyl group, /, /-dimethyl-3
, 3-dimethylbutyl group, amyl group, hexyl group, etc.
、７． ｌｌ、 、！ｔ、 ４−ジベンゾ−／、−一オ
キサホスファンーＪ−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。,7. ll, ,! It is obtained by reacting t,4-dibenzo-/,-monooxaphosphane-J-oxide with hydroquinone.
本発明の共重合ポリエステルを製造するには。To produce the copolymerized polyester of the present invention.
例えば、アセトキシハイドロキノン酵導体、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
を前記モル比になるように仕込み、コアｊ℃に昇温し２
時間攪拌後、減圧下（Ｏ，ｊｍｉＨｇ）で、ｔ −ｆｆ
時間重合すればよい。For example, each component of acetoxyhydroquinone fermentation conductor, paraacetoxybenzoic acid, terephthalic acid, and isophthalic acid is charged in the molar ratio as described above, heated to core j℃, and heated to 2.
After stirring for an hour, under reduced pressure (O, jmiHg), t -ff
It is sufficient to polymerize over time.
このサーモトロピッ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ィルムとすることがで
きる。This thermotropic liquid crystalline copolyester can be melt-formed under shearing and drafting to form a highly oriented film with excellent transparency.
浴液状態あるいは溶融状態で液晶性を示す高分子化合物
（液晶性ボ１７．）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、フィルム
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Ｋより得られる繊維、フィル
ムは不透明なものであり、偏光フィルムなどの光学的用
途への応用は不可能であった。The high orientation of polymer compounds that exhibit liquid crystallinity in a bath liquid state or molten state (liquid crystalline compound 17.) is known as a technique for processing them into highly elastic fibers and films by solution, melt spinning, or film forming. However, fibers and films obtained from K are opaque due to non-uniformity of the liquid crystalline polymer and dislocation of the liquid crystal phase, making it impossible to apply them 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ック液晶性共重
合ポリエステルフィルムに透明性が付与され、かつ該フ
ィルムの高配向性を利用し二色性色素を染着配向させ、
偏光フィ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, transparency is imparted to a thermotropic liquid crystalline copolyester film, and the dichroic dye is dyed and oriented using the high orientation of the film,
The use of polarizing film is an extremely innovative development.
上記の液晶性共重合ポリエステル樹脂から偏光フィルム
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
瞑される。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 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−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, etc., which have dichroism in their molecular structure, and has the following structural formula, for example. It is something.
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。As the dichroic dye, the above-mentioned ones may be used alone or as a mixture of several types.
使用方法は、例えばサーモトロピック液晶性共重合ポリ
エステルとトライブレンド、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
０．０／重量％以上ＩＯ′Ｍ−＃、％未滴の間から選ば
れるのが好ましい。The method of use is, for example, by mixing it with a thermotropic liquid crystalline copolyester by methods such as triblending, melt blending, and solvent mixing. The amount of the dichroic dye to be mixed is preferably selected from 0.0% by weight or more and IO'M-#,% by weight.
本発明に用いるす―モトロピッ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ィルムを製造できることである。The characteristics of the Sumotropic liquid crystalline copolymerized polyester used in the present invention are that it exhibits high alignment performance with only a very simple process of melt film formation, and it can be easily formed into a polarizing film by blending a dichroic dye during film formation. It is something that can be manufactured.
このことは通常のポリマーの場合、配向フィルムを得よ
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ィルムを製造する方法は新規
なものである。This is a major advantage in terms of production costs compared to the case of ordinary polymers, which require some kind of stretching treatment after film formation in order to obtain an oriented film. The method of manufacturing is new.
浴融製膜は通常矩形、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。The bath melt film is usually formed 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ッ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、その結果としてフィ
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 segments are oriented in the flow direction due to the rigidity of the resin segments, and as a result, transparency is imparted to the film.
製ＦＡ温度は本発明のサーモトロピック液晶性共重合ポ
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、通常コ３０℃〜ｇｏｏ℃の範囲で行なわれ
る。The production FA temperature may be within a temperature range in which the thermotropic liquid crystal copolymerized polyester of the present invention exhibits liquid crystallinity (anisotropy when melted), and is usually carried out in the range of 30°C to 30°C.
以上のようにして得られた偏光フィルムはサーモトロピ
ッ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ィルムとして
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ィルムはそれ自体で
すぐれた力学的性質、耐熱、耐水、耐候性を有し、これ
よりなる偏光フィルムは高温、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 thermotropic liquid crystalline copolymer polyester, and has breakthrough transparency for a film using liquid crystalline copolyester. This copolymerized polyester film itself has excellent mechanical properties, heat resistance, water resistance, and weather resistance, and the polarizing film made of it has no deterioration in polarizing performance under high temperature and high humidity conditions. Don't wake up.
又、使用目的によっては他のプラスチックとのラミネー
ションや共押出し等により偏光フィルムを保護した状態
で使用してもよく、さらには偏光フィルム自体、あるい
は保護層を介して、表面に蒸着、スパッタリングまたは
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。Furthermore, depending on the purpose of use, the polarizing film may be used in a protected state by lamination or coextrusion with other plastics, or it may be used by vapor deposition, sputtering, or coating on the surface of the polarizing film itself or through a protective layer. A transparent conductive film made of indium-tin oxide or the like is formed by this method and put into 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 unless the gist of the invention is exceeded.
実施例に先だって下記項目の測定法について記載する。Prior to working examples, methods for measuring 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
デジタル濁度計ＮＤＨ−２０Ｄ
（日本電色工業株式会社製）
を用いＪ工８ＫＡ７１Ｑに準じ
た。Parallel light transmittance: Using an integrating sphere type light transmittance measuring device, digital turbidity meter NDH-20D (manufactured by Nippon Denshoku Kogyo Co., Ltd.), according to J-8KA71Q.
Ｆ ｄｙｅ値・・・・・・・・・・・・・・・分光光度
計−一を形（日立製作所りを用いて入射光
線の偏光面と配向軸が垂直、
平行の場合の透過率１１、■。F dye value: Transmittance 11 when the polarization plane of the incident light and the orientation axis are perpendicular and parallel using a spectrophotometer (Hitachi) ,■.
を可視領域において測定し、 次式に基づく配向係数 （Ｐ ｄｙｅ ）を算出した。is measured in the visible range, Orientation coefficient based on the following formula (P dye) was calculated.
Ｆ ａ７ｅ＝＝ （Ｄ−／）／（Ｄ＋！、）（但し、Ｄ
は吸収二色比で
あり、
Ｄ＝ＬＯｇ（工。／釉）／Ｌｏｇ（工。／工、）工。は
同一延伸処理条件の無
染色フィルムの透過率であ
る）
Ｆ ｄｙｅ値は二色性色素の配
内皮を表わし、ＩＦ ｄｙｅ値が
犬なることは偏光フィルム
の偏光性能が大なることを
示す。F a7e== (D-/)/(D+!,) (However, D
is the absorption dichroic ratio, D=LOg(technique/glaze)/Log(technique/technique,)technique. is the transmittance of an undyed film under the same stretching conditions.) The F dye value represents the endothelium of the dichroic dye, and a small IF dye value indicates that the polarizing performance of the polarizing film is high.
実施例１ 重合した高分子化合物なＴダイ（ダイ幅ｉｘ。Example 1 Polymerized polymer compound T-die (die width ix.
朋；リップクリアランス０．２ ｍ ）を備えた３０ｍ
ｘ ｐ押出機を用いて、温度３’ｌＯ℃、剪断速度！
００５ｅｃ−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ィルムは透明で、その平行光線透
過率はフィルム厚２５μｍで１７％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、３ｅｃ℃で溶融時異方性を示すことを確認した
。30m with lip clearance 0.2m)
x p extruder, temperature 3'lO ℃, shear rate!
The film was formed under the conditions of 005ec-1 and a draft ratio of 10. The undyed film obtained at this time was transparent, and its parallel light transmittance was 17% at a film thickness of 25 μm. Furthermore, 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 3 ec°C.
次に上記サーモトロピック液晶性高分子化合物に下記式
で示される色素を
ヘンシェルミキサーで０．ｊｆＸ量％の割合に混合した
のち上記と同様の方法でＴダイ製膜を行ない青色の偏光
フィルムを製造した。得られた偏光フィルムのＦｃＬｙ
ｅ値はＯ９９５であった。Next, a dye represented by the following formula was added to the thermotropic liquid crystalline polymer compound using a Henschel mixer at 0.00%. After mixing at a ratio of % jf FcLy of the obtained polarizing film
The e value was O995.
比較例１
ポリエチレンテレフタレート成分がＳＯ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７３、温度を２７！ｒ’Ｃとした
以外は実施例１と全く同様の製膜な行なった。得られた
無染色フィルムの平行光線透過率はフィルム厚ｌ！μｍ
で３０％と不透明なものであった。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
察したところコク３℃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ック液晶性高分子化合物であ
ることを確認した。Comparative Example 1 A copolymerized polyester with a polyethylene terephthalate component of SO mol% and a parahydroxybenzoic acid component of 50 mol% was prepared at a draft ratio of 73 and a temperature of 27! Film formation was carried out in exactly the same manner as in Example 1, except that r'C was used. The parallel light transmittance of the obtained undyed film is equal to the film thickness l! μm
It was unclear at 30%. When this copolyester was observed under a polarizing microscope equipped with a heat stage, it showed melting anisotropy at 3°C, confirming that the copolyester was also a thermotropic liquid crystalline polymer compound.
次に実施例１と同一の色素を実施例／と同様の方法で混
合した後上記と同様の方法でＴダイ製膜を行なったがＦ
ｄ７θ値はＯ，ＩＩａと配向性も低いフィルムであっ
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 d7θ value was O, IIa, indicating that the film had low orientation.
以上のように本発明のサーモトロピック液晶性共重合ポ
リエステルは無染色時のフィルムは平行光線透過率が１
０％以上と高く、またこれを用いた偏光フィルムも透明
性が良好で配向係Ｍ Ｉ’ ｄＦｅ値が００３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 1 when undyed.
It can be seen that the polarizing film using this film has good transparency and has a high orientation coefficient M I' dFe value of 003 or more, indicating a high polarizing ability.
本発明によれば簡便な方法で、透明性、偏光性能等に優
れたフィ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, polarization performance, etc. can be obtained by a simple method, and is very effective in practice.
Claims (2)
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（Ａ）対（Ｄ）の組
成比がモル％で５対９５から７０対３０かつ、（Ｂ）対
（Ｃ）の組成比がモル％で５０対５０から１００対０の
間であることを特徴とする偏光フィルム。(1) A polarizing film made of a thermotropic liquid crystalline polyester film in which a dichroic dye is dyed and oriented, the thermotropic liquid crystalline polyester being a hydroquinone derivative component (A), a terephthalic acid component (B), and an isophthalic acid component. (C) and parahydroxybenzoic acid component (
A copolymerized polyester consisting of D) in which the composition ratio of (A) to (D) is 5:95 to 70:30 in mol%, and the composition ratio of (B) to (C) is 50:50 to 100 in mol% A polarizing film characterized in that the polarizing film is between 0 and 0.
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成分であることを特徴とする
特許請求の範囲第１項に記載の偏光フィルム。 ▲数式、化学式、表等があります▼・・・（ I ）▲数
式、化学式、表等があります▼・・・（II） （（ I ）、（II）式中、Ｘ、Ｘ′は同一又は異なって
いてもよく、炭素数１〜８のアルキル基又は▲数式、化
学式、表等があります▼の基を表わす。）(2) The hydroquinone derivative component (A) has the following general formula (
The polarizing film according to claim 1, which is a component formed from a compound represented by I) or (II), or an acylated product thereof. ▲There are mathematical formulas, chemical formulas, tables, etc.▼...(I)▲There are mathematical formulas, chemical formulas, tables, etc.▼...(II) (In the formulas (I) and (II), X and X' are the same or They may be different and represent an alkyl group with 1 to 8 carbon atoms or a group ▲with numerical formulas, chemical formulas, tables, etc.)
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 true JPS63195602A (en) | 1988-08-12 |
| JPH0795123B2 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) |
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0445674A2 (en) * | 1990-03-07 | 1991-09-11 | Hoechst Aktiengesellschaft | Method of orienting liquid crystal polymers and their use as orientation layer in liquid crystal switching and display device |
| US5408347A (en) * | 1990-07-18 | 1995-04-18 | Hoechst Aktiengesellschaft | Polyester based liquid-crystal display device |
| WO1996038747A1 (en) * | 1995-06-02 | 1996-12-05 | Hoechst Celanese Corporation | Process for preparing high performance polarizer films |
| WO1996038745A1 (en) * | 1995-06-02 | 1996-12-05 | Hoechst Celanese Corporation | High extinction polarizer films comprising liquid crystal polymeric moieties |
| WO1996038746A1 (en) * | 1995-06-02 | 1996-12-05 | Hoechst Celanese Corporation | Polariser films with high thermal and hygroscopic stability |
| WO1997019374A1 (en) * | 1995-11-21 | 1997-05-29 | Hoechst Celanese Corporation | Polarizer films comprising aromatic liquid crystalline polymers comprising dichroic dyes in their main chains |
| WO1997023790A1 (en) * | 1995-12-14 | 1997-07-03 | Hoechst Celanese Corporation | Polarizer films comprising wholly aromatic liquid crystalline polymers and dichroic dyes |
| US5672296A (en) * | 1995-06-02 | 1997-09-30 | 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 |
| US5851423A (en) * | 1997-05-22 | 1998-12-22 | Hoechst Celanese Corporation | Liquid crystal display devices incorporating polarizers comprising liquid crystal polymers |
| US5863622A (en) * | 1996-12-05 | 1999-01-26 | Hoechst Celanese Corporation | Polarizer laminates comprising coextruded liquid crystal polymer moieties and integral thermoplastic cover layers |
| 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 |
| 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 |
| 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 |
Citations (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
Patent Citations (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 |
Cited By (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0445674A2 (en) * | 1990-03-07 | 1991-09-11 | Hoechst Aktiengesellschaft | Method of orienting liquid crystal polymers and their use as orientation layer in liquid crystal switching and display device |
| US5408347A (en) * | 1990-07-18 | 1995-04-18 | Hoechst Aktiengesellschaft | Polyester based liquid-crystal display device |
| US5672296A (en) * | 1995-06-02 | 1997-09-30 | Hoechst Celanese Corp. | Polarizer films comprising wholly aromatic liquid crystalline polymers and dichroic dyes |
| WO1996038745A1 (en) * | 1995-06-02 | 1996-12-05 | Hoechst Celanese Corporation | High extinction polarizer films comprising liquid crystal polymeric moieties |
| WO1996038746A1 (en) * | 1995-06-02 | 1996-12-05 | Hoechst Celanese Corporation | Polariser films with high thermal and hygroscopic stability |
| US5753145A (en) * | 1995-06-02 | 1998-05-19 | Hoecst Celanese Corp. | Polarizer films with high thermal and hygroscopic stability |
| US5667719A (en) * | 1995-06-02 | 1997-09-16 | Hoechst Celanese Corp. | High extinction polarizer films comprising liquid crystal polymeric moieties |
| WO1996038747A1 (en) * | 1995-06-02 | 1996-12-05 | Hoechst Celanese Corporation | Process for preparing high performance polarizer films |
| US5707566A (en) * | 1995-06-02 | 1998-01-13 | Hoechst Celanese Corp. | Process for preparing high performance polarizer films |
| WO1997019374A1 (en) * | 1995-11-21 | 1997-05-29 | Hoechst Celanese Corporation | Polarizer films comprising aromatic liquid crystalline polymers comprising dichroic dyes in their main chains |
| 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 |
| WO1997023790A1 (en) * | 1995-12-14 | 1997-07-03 | Hoechst Celanese Corporation | 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 |
| 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 |
| 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 |
| 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0795123B2 (en) | 1995-10-11 |
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