JP2002155218A - Tris-azo compound or its salt and polarizing dye membrane including the same - Google Patents
Tris-azo compound or its salt and polarizing dye membrane including the sameInfo
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- JP2002155218A JP2002155218A JP2000357358A JP2000357358A JP2002155218A JP 2002155218 A JP2002155218 A JP 2002155218A JP 2000357358 A JP2000357358 A JP 2000357358A JP 2000357358 A JP2000357358 A JP 2000357358A JP 2002155218 A JP2002155218 A JP 2002155218A
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- salt
- polarizing film
- dye
- film
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Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、トリスアゾ化合物
又はその塩及びそれを含有してなる染料系偏光膜に関す
るものである。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a trisazo compound or a salt thereof and a dye-based polarizing film containing the same.
【０００２】[0002]
【従来の技術】偏光膜は、延伸配向したポリビニルアル
コール系のフィルム又は、ポリ塩化ビニルフィルムの脱
塩酸若しくはポリビニルアルコール系フィルムの脱水に
よりポリエンを生成して配向せしめたポリエン系のフィ
ルムなどの偏光膜基材に、偏光素子としてヨウ素や二色
性染料を含有させて製造される。これらのうち、ヨウ素
系偏光膜は、初期偏光性能には優れるものの、熱に対す
る耐久性や水に対する耐久性が劣るため、高温・高湿の
状態ではその性能が低下するという問題がある。このよ
うな耐久性を向上させるために、ホルムアルデヒド又は
ホウ酸を含む水溶液で処理する方法や、透湿度の低い高
分子フィルムを保護膜として用いる方法などが考えられ
ているが、未だ十分とはいえない。2. Description of the Related Art A polarizing film is a polarizing film such as a stretch-oriented polyvinyl alcohol-based film or a polyene-based film oriented by generating polyene by dehydrochlorination of a polyvinyl chloride film or dehydration of a polyvinyl alcohol-based film. It is manufactured by adding iodine or a dichroic dye as a polarizing element to a base material. Among them, the iodine-based polarizing film is excellent in initial polarization performance, but has poor durability against heat and water, and thus has a problem that its performance deteriorates at high temperature and high humidity. In order to improve such durability, a method of treating with an aqueous solution containing formaldehyde or boric acid, a method of using a polymer film having low moisture permeability as a protective film, and the like have been considered, but it is still sufficient. Absent.
【０００３】一方、偏光素子として二色性染料を用いた
染料系偏光膜は、ヨウ素系偏光膜に比べて熱及び水に対
する耐久性に優れるものの、一般に初期偏光性能が劣る
傾向があり、特に初期偏光性能に優れた偏光膜用染料が
要望されている。[0003] On the other hand, a dye-based polarizing film using a dichroic dye as a polarizing element is excellent in durability against heat and water as compared with an iodine-based polarizing film, but generally tends to have poor initial polarization performance. There is a demand for a dye for a polarizing film having excellent polarization performance.
【０００４】[0004]
【発明が解決しようとする課題】本発明者は、偏光膜製
造時の染色性が良好であり、偏光性能や、高温、高湿条
件における耐久性及び耐光性に優れ、且つ、高分子フィ
ルムに２種類以上の二色性染料を吸着配向させてなる液
晶プロジェクター用途等の偏光膜において、５００〜５
８０nmの範囲の領域をカバーする染料を探索した結果、
特定のアゾ化合物又はその塩が上記目的を達成すること
を見出して、本発明を完成するに至った。SUMMARY OF THE INVENTION The present inventors have found that the dyeing properties during the production of a polarizing film are good, the polarizing performance, the durability under high-temperature and high-humidity conditions and the light resistance are excellent, and that the polymer film is excellent. In a polarizing film for use in a liquid crystal projector or the like in which two or more dichroic dyes are adsorbed and aligned, 500 to 5
As a result of searching for a dye covering the range of 80 nm,
The present inventors have found that a specific azo compound or a salt thereof achieves the above object, and have accomplished the present invention.
【０００５】[0005]
【課題を解決するための手段】すなわち、本発明は、
（イ）下式（Ｉ）That is, the present invention provides:
(A) The following formula (I)
【０００６】[0006]
【化２】 Embedded image
【０００７】（式中、Ａは、１〜３個のスルホ基を有す
るナフチルを表し、Ｒ1、Ｒ2、Ｒ3及びＲ4は、同一又は
相異なり、水素又は低級アルキルを表す。）で示される
トリスアゾ化合物又はその塩、並びに、（ロ）上記
（イ）のトリスアゾ化合物又はその塩を偏光膜基材に含
有してなる染料系偏光膜を提供するものである。以下、
本発明を詳細に説明する。Wherein A represents naphthyl having 1 to 3 sulfo groups, and R 1 , R 2 , R 3 and R 4 are the same or different and represent hydrogen or lower alkyl. The present invention provides a trisazo compound or a salt thereof, and (b) a dye-based polarizing film comprising the above-mentioned trisazo compound or a salt thereof (a) in a polarizing film base material. Less than,
The present invention will be described in detail.
【０００８】[0008]
【発明の実施の形態】上式（Ｉ）におけるＡは、１〜３
個のスルホ基を有するナフチルである。上記Ａで示され
るナフチルとしては、スルホを２個有するジスルホナフ
チルが好ましく、ジスルホ−２−ナフチルが特に好まし
い。Ａで示されるナフチルとしては、例えば、５−、６
−、７−又は８−スルホ−２−ナフチル、４−、５−、
６−又は７−スルホ−１−ナフチル、１，５−、６，８
−、４，８−、５，７−又は３，６−ジスルホ−２−ナ
フチル、３，６−又は４，６−ジスルホ−１−ナフチ
ル、１，５，７−、３，６，８−又は４，６，８−トリ
スルホ−２−ナフチル等が挙げられる。BEST MODE FOR CARRYING OUT THE INVENTION A in the above formula (I) is 1 to 3
Is a naphthyl having two sulfo groups. As the naphthyl represented by A, disulfonaphthyl having two sulfo is preferable, and disulfo-2-naphthyl is particularly preferable. As naphthyl represented by A, for example, 5-, 6
-, 7- or 8-sulfo-2-naphthyl, 4-, 5-,
6- or 7-sulfo-1-naphthyl, 1,5-, 6,8
-, 4,8-, 5,7- or 3,6-disulfo-2-naphthyl, 3,6- or 4,6-disulfo-1-naphthyl, 1,5,7-, 3,6,8- Or 4,6,8-trisulfo-2-naphthyl and the like.
【０００９】Ｒ1、Ｒ2、Ｒ3及びＲ4は、同一又は相異な
り、水素又は低級アルキルであり、該低級アルキルとし
ては、炭素数１〜４の直鎖もしくは分岐状のものが好ま
しい。低級アルキルの具体例としては、メチル、エチル
及びプロピルなどが挙げられる。上記のＲ1、Ｒ2、Ｒ3
及びＲ4としては、水素又はメチルが好ましい。R 1 , R 2 , R 3 and R 4 are the same or different and are hydrogen or lower alkyl, and the lower alkyl is preferably a straight or branched one having 1 to 4 carbon atoms. Specific examples of lower alkyl include methyl, ethyl and propyl. The above R 1 , R 2 , R 3
And R 4 are preferably hydrogen or methyl.
【００１０】トリスアゾ化合物（Ｉ）又はその塩は、例
えば、以下に述べる方法によって製造することができ
る。即ち、先ず、下式（II）The trisazo compound (I) or a salt thereof can be produced, for example, by the following method. That is, first, the following formula (II)
【００１１】[0011]
【化３】 Embedded image
【００１２】（式中、Ａ、Ｒ1、Ｒ2、Ｒ3及びＲ4は前記
の意味を表す。）で示される化合物を、酸性の水性媒体
中、５〜４０℃の条件下で亜硝酸ナトリウムと反応させ
て、ジアゾ化する。得られたジアゾ化物を、下式(ＩＩ
Ｉ)(Wherein A, R 1 , R 2 , R 3 and R 4 have the same meanings as described above), and the nitrous acid is reacted in an acidic aqueous medium at 5 to 40 ° C. React with sodium to diazotize. The obtained diazotized compound is represented by the following formula (II)
I)
【００１３】[0013]
【化４】 Embedded image
【００１４】（式中、Ｂはアミノフェニル基を表す。）
で示される化合物と、水性媒体中、５〜４０℃、ｐＨ６
〜１１の条件下でカップリング反応させることにより、
式（Ｉ）で示されるトリスアゾ化合物又はその塩を得る
ことができる。(Wherein B represents an aminophenyl group)
And a compound represented by the formula:
By performing a coupling reaction under the conditions of ~ 11,
The trisazo compound represented by the formula (I) or a salt thereof can be obtained.
【００１５】上記トリスアゾ化合物（Ｉ）が塩の形で存
在する場合、その塩としては、例えば、リチウム、ナト
リウムやカリウム塩のようなアルカリ金属塩、アンモニ
ウム塩、及び、エタノールアミン塩やアルキルアミン塩
のような有機アミン塩等が挙げられる。トリスアゾ化合
物（Ｉ）を偏光膜基材に含有させる場合は、ナトリウム
塩の形で用いるのが好ましい。When the trisazo compound (I) is present in the form of a salt, the salt may be, for example, an alkali metal salt such as lithium, sodium or potassium salt, an ammonium salt, an ethanolamine salt or an alkylamine salt. And organic amine salts such as When the trisazo compound (I) is contained in the polarizing film substrate, it is preferably used in the form of a sodium salt.
【００１６】トリスアゾ化合物（Ｉ）又はその塩を偏光
膜基材に含有させて偏光膜とする場合は、他の有機染料
と併用することにより、色相を補正し、偏光性能を向上
させることができる。この場合に用いられる有機染料と
しては、二色性の高いものであればいかなる染料でもよ
いが、特に耐光性に優れる染料を選択することにより、
液晶プロジェクター用途に適した偏光膜とすることがで
きる。When the trisazo compound (I) or a salt thereof is contained in a polarizing film substrate to form a polarizing film, the hue can be corrected and the polarizing performance can be improved by using it together with another organic dye. . As the organic dye used in this case, any dye may be used as long as it has high dichroism, but by selecting a dye having excellent light resistance,
A polarizing film suitable for a liquid crystal projector can be obtained.
【００１７】かかる有機染料の具体例としては、カラー
・インデックス・ジェネリック・ネーム(Color Index
Generic Name)で表して、以下のものが例示される。Specific examples of such organic dyes include a color index generic name (Color Index).
Generic Name), the following are exemplified.
【００１８】シー・アイ・ダイレクト・イエロー12 シー・アイ・ダイレクト・イエロー28 シー・アイ・ダイレクト・イエロー44 シー・アイ・ダイレクト・オレンジ26 シー・アイ・ダイレクト・オレンジ39 シー・アイ・ダイレクト・オレンジ107 シー・アイ・ダイレクト・レッド2 シー・アイ・ダイレクト・レッド31 シー・アイ・ダイレクト・レッド79 シー・アイ・ダイレクト・レッド81 シー・アイ・ダイレクト・レッド247Sea Eye Direct Yellow 12 Sea Eye Direct Yellow 28 Sea Eye Direct Yellow 44 Sea Eye Direct Orange 26 Sea Eye Direct Orange 39 Sea Eye Direct Orange 107 C I Direct Red 2 C I Direct Red 31 C I Direct Red 79 C I Direct Red 81 C I Direct Red 247
【００１９】本発明の染料系偏光膜は、トリスアゾ化合
物（Ｉ）又はその塩からなる、あるいは、さらに他の有
機染料を含んでなる二色性染料を、偏光膜基材である高
分子フィルムに公知の方法で含有させることによって、
製造することができる。この高分子フィルムとしては、
例えば、ポリビニルアルコール系の樹脂、ポリ酢酸ビニ
ル樹脂、エチレン／酢酸ビニル（ＥＶＡ）樹脂、ナイロ
ン樹脂、ポリエステル樹脂などからなるものが利用され
る。ここでいうポリビニルアルコール系の樹脂には、ポ
リ酢酸ビニルの部分又は完全ケン化物であるポリビニル
アルコール自体のほか、ケン化ＥＶＡ樹脂のような、酢
酸ビニルと他の共重合可能な単量体、例えば、エチレン
やプロピレンのようなオレフィン類、クロトン酸やアク
リル酸、メタクリル酸、マレイン酸のような不飽和カル
ボン酸類、不飽和スルホン酸類、ビニルエーテル類など
との共重合体のケン化物、さらにはポリビニルアルコー
ルをアルデヒドで変性したポリビニルホルマールやポリ
ビニルアセタールなども包含される。偏光膜基材として
は、ポリビニルアルコール系のフィルム、特にポリビニ
ルアルコールフィルムが、染料の吸着性及び配向性の点
から、好適に用いられる。The dye-based polarizing film of the present invention comprises a dichroic dye comprising a trisazo compound (I) or a salt thereof, or a dichroic dye further containing another organic dye, is added to a polymer film as a polarizing film base material. By containing by a known method,
Can be manufactured. As this polymer film,
For example, a resin made of a polyvinyl alcohol resin, a polyvinyl acetate resin, an ethylene / vinyl acetate (EVA) resin, a nylon resin, a polyester resin, or the like is used. The polyvinyl alcohol-based resin referred to here includes, in addition to polyvinyl alcohol itself, which is a partially or completely saponified product of polyvinyl acetate, a monomer copolymerizable with vinyl acetate, such as a saponified EVA resin, for example, Saponified copolymers with olefins such as ethylene and propylene, unsaturated carboxylic acids such as crotonic acid, acrylic acid, methacrylic acid and maleic acid, unsaturated sulfonic acids and vinyl ethers, and further polyvinyl alcohol And aldehyde-modified polyvinyl formal and polyvinyl acetal. As the polarizing film substrate, a polyvinyl alcohol-based film, particularly a polyvinyl alcohol film, is suitably used from the viewpoint of the dye adsorbing property and orientation.
【００２０】このような高分子フィルムに二色性染料を
含有させるにあたっては、通常、高分子フィルムを染色
する方法が採用される。染色は、例えば次のようにして
行うことができる。まず、二色性染料を水に溶解して染
浴を調製する。染浴中の染料濃度は特に制限されない
が、通常は０.０００１〜１０重量％の範囲から選択さ
れる。また、必要により染色助剤を用いてもよく、例え
ば、芒硝を染浴中で１〜１０重量％用いるのが好適であ
る。このようにして調製した染浴に高分子フィルムを浸
漬し、染色を行う。染色温度は、好ましくは４０〜８０
℃である。二色性染料の配向は、高分子フィルムを延伸
することによって行われる。延伸する方法としては、例
えば湿式法や乾式法など、公知のいずれの方法を採用し
てもよい。高分子フィルムの延伸は、染色の前に行って
も、染色の後に行ってもよい。When a dichroic dye is contained in such a polymer film, a method of dyeing the polymer film is usually employed. Staining can be performed, for example, as follows. First, a dichroic dye is dissolved in water to prepare a dye bath. The dye concentration in the dye bath is not particularly limited, but is usually selected from the range of 0.0001 to 10% by weight. If necessary, a dyeing aid may be used. For example, it is preferable to use sodium sulfate in an amount of 1 to 10% by weight in a dyeing bath. The polymer film is immersed in the dyeing bath prepared in this way to perform dyeing. The dyeing temperature is preferably 40-80.
° C. The dichroic dye is oriented by stretching the polymer film. As a stretching method, any known method such as a wet method or a dry method may be employed. Stretching of the polymer film may be performed before or after dyeing.
【００２１】二色性染料を含有させ、配向させた高分子
フィルムは、必要に応じて、公知の方法によりホウ酸処
理などの後処理が施される。このような後処理は、偏光
膜の光線透過率、偏光度及び耐久性を向上させる目的で
行われる。ホウ酸処理の条件は、用いる高分子フィルム
の種類や用いる染料の種類によって異なるが、一般的に
は、ホウ酸水溶液のホウ酸濃度を１〜１５重量％、好ま
しくは５〜１０重量％の範囲とし、処理は３０〜８０
℃、好ましくは５０〜８０℃の温度範囲で行われる。さ
らには必要に応じて、カチオン系高分子化合物を含む水
溶液でフィックス処理を併せて行ってもよい。The oriented polymer film containing the dichroic dye is subjected to post-treatment such as boric acid treatment by a known method, if necessary. Such a post-treatment is performed for the purpose of improving the light transmittance, the degree of polarization, and the durability of the polarizing film. The conditions of the boric acid treatment vary depending on the type of the polymer film to be used and the type of the dye to be used, but generally, the boric acid concentration of the aqueous boric acid solution is in the range of 1 to 15% by weight, preferably 5 to 10% by weight. And the processing is 30 to 80
C., preferably at a temperature in the range of 50 to 80C. Further, if necessary, the fix treatment may be performed together with an aqueous solution containing a cationic polymer compound.
【００２２】このようにして得られる染料系偏光膜は、
その片面又は両面に、光学的透明性及び機械的強度に優
れる保護膜を貼合して、偏光板とすることができる。保
護膜を形成する材料は、従来から使用されているもので
よく、例えば、セルロースアセテート系フィルムやアク
リル系フィルムのほか、四フッ化エチレン／六フッ化プ
ロピレン共重合体のようなフッ素樹脂系フィルム、ポリ
エステル系フィルム、ポリオレフィン系フィルム、ポリ
アミド系フィルムなどが用いられる。The dye-based polarizing film thus obtained is
A polarizing plate can be obtained by laminating a protective film having excellent optical transparency and mechanical strength on one or both surfaces thereof. The material for forming the protective film may be a conventionally used material, for example, a cellulose acetate film or an acrylic film, or a fluororesin film such as an ethylene tetrafluoride / propylene hexafluoride copolymer. And polyester-based films, polyolefin-based films, polyamide-based films, and the like.
【００２３】[0023]
【実施例】以下、実施例により本発明をさらに詳細に説
明するが、本発明はこれらの例により、何ら限定される
ものではない。例中の「％」及び「部」は、特記ない限
り、重量％及び重量部である。EXAMPLES The present invention will be described in more detail with reference to the following Examples, which should not be construed as limiting the invention thereto. "%" And "parts" in the examples are% by weight and parts by weight unless otherwise specified.
【００２４】実施例１ 下式（１）Embodiment 1 The following equation (1)
【００２５】[0025]
【化５】 Embedded image
【００２６】で示される化合物４．５部と亜硝酸ナトリ
ウム０．８部を水９０部とＮ−メチルピロリドン４５部
の混合液に加え、常温で攪拌しながら、３５％塩酸１０
部を加えて、２時間攪拌し、ジアゾ体を得た。他方、遊
離酸の形が下式（２）To a mixture of 90 parts of water and 45 parts of N-methylpyrrolidone was added 4.5 parts of the compound represented by the following formula, and 0.8 parts of sodium nitrite.
Was added and stirred for 2 hours to obtain a diazo compound. On the other hand, the form of the free acid is represented by the following formula (2)
【００２７】[0027]
【化６】 Embedded image
【００２８】で示される化合物３．５部を水４０部に加
えて、常温でｐＨ７．５に調整した。攪拌下に、先に得
たジアゾ体を２時間かけて仕込み、更に２時間保温し
て、下式（３）3.5 parts of the compound represented by the above formula was added to 40 parts of water, and the pH was adjusted to 7.5 at room temperature. Under stirring, the diazo compound obtained above was charged over 2 hours, and the temperature was further maintained for 2 hours to obtain the following formula (3)
【００２９】[0029]
【化７】 Embedded image
【００３０】で示されるトリスアゾ化合物を得た。この
化合物は、水性媒体中でλmax５３７nmを示した。A trisazo compound represented by the following formula was obtained. This compound exhibited a λmax of 537 nm in an aqueous medium.
【００３１】実施例２ 原料化合物を変更する以外は、実施例１に準拠すること
により、下式（４）で示されるトリスアゾ化合物の塩を
得た。この化合物は、水性媒体中でλmax５４５nmを示
した。Example 2 A salt of a trisazo compound represented by the following formula (4) was obtained in the same manner as in Example 1 except that the starting compound was changed. This compound exhibited a λmax of 545 nm in an aqueous medium.
【００３２】[0032]
【化８】 Embedded image
【００３３】合成例１ 原料化合物を変更する以外は、実施例１に準拠すること
により、それぞれ、下式（５）、（６）、（７）及び
（８）で示されるアゾ化合物の塩を得ることができる。Synthesis Example 1 A salt of an azo compound represented by the following formulas (5), (6), (7) and (8) was prepared in the same manner as in Example 1 except that the starting compound was changed. Obtainable.
【００３４】[0034]
【化９】 Embedded image
【００３５】[0035]
【化１０】 Embedded image
【００３６】実施例３ 厚さ７５μm のポリビニルアルコールフィルム［クラレ
ビニロン＃７５００、（株）クラレ製品］を縦一軸に５
倍延伸して、偏光膜基材とした。このポリビニルアルコ
ールフィルムを緊張状態に保ったまま、実施例１で得ら
れた式（３）で示されるトリスアゾ化合物の塩を０.０
２５％、染色助剤である芒硝を２.０％の濃度とした７
０℃の水溶液に浸漬した。次に７８℃の７.５％ホウ酸
水溶液に５分間浸漬したのち取り出して、２０℃の水で
２０秒間洗浄し、５０℃で乾燥することにより、偏光膜
を得た。得られた偏光膜のλmax （膜の延伸方向の透過
率が最小となる波長）は５５０nmであり、この偏光膜は
高い偏光度を有し、高温・高湿の状態でも長時間にわた
る耐久性を示した。また、長時間暴露に対する耐光性に
も優れていた。Example 3 A 75 μm thick polyvinyl alcohol film [Kuraray Vinylon # 7500, a product of Kuraray Co., Ltd.] was coated with 5
The film was stretched twice to obtain a polarizing film substrate. With the polyvinyl alcohol film kept in a strained state, the salt of the trisazo compound represented by the formula (3) obtained in Example 1 was added to 0.0
25%, and sodium sulfate, a dyeing aid, at a concentration of 2.0% 7
It was immersed in an aqueous solution at 0 ° C. Next, the film was immersed in a 7.5% aqueous solution of boric acid at 78 ° C. for 5 minutes, taken out, washed with water at 20 ° C. for 20 seconds, and dried at 50 ° C. to obtain a polarizing film. The obtained polarizing film has a λmax (wavelength at which the transmittance in the stretching direction of the film is minimum) of 550 nm, and this polarizing film has a high degree of polarization and has a long-term durability even in a high temperature and high humidity state. Indicated. Also, the light resistance to long-term exposure was excellent.
【００３７】実施例４ 染色浴の温度を６５℃に、またホウ酸処理の温度を７３
℃に変更して、実施例３と同様の処理を施すことにより
偏光膜を得た。得られた偏光膜のλmax は５５０nmであ
った。この偏光膜は高い偏光度を有し、高温・高湿の状
態でも長時間にわたる耐久性を示した。また、長時間暴
露に対する耐光性にも優れていた。Example 4 The temperature of the dyeing bath was 65 ° C. and the temperature of the boric acid treatment was 73 ° C.
The temperature was changed to ° C., and the same treatment as in Example 3 was performed to obtain a polarizing film. The λmax of the obtained polarizing film was 550 nm. This polarizing film had a high degree of polarization and exhibited long-term durability even in a high-temperature and high-humidity state. Also, the light resistance to long-term exposure was excellent.
【００３８】実施例５ 染料を実施例１で得られた式（３）で示されるトリスア
ゾ化合物の塩を実施例２で得られた式（４）で示される
アゾ化合物の塩に変更した他は実施例３と同様の処理を
施すことにより偏光膜を得た。得られた偏光膜のλmax
は５５０nmであった。この偏光膜は高い偏光度を有し、
高温・高湿の状態でも長時間にわたる耐久性を示した。
また、長時間暴露に対する耐光性にも優れていた。Example 5 The dye was changed from the salt of the trisazo compound of the formula (3) obtained in Example 1 to the salt of the azo compound of the formula (4) obtained in Example 2, except that By performing the same processing as in Example 3, a polarizing film was obtained. Λmax of the obtained polarizing film
Was 550 nm. This polarizing film has a high degree of polarization,
It exhibited long-term durability even in high temperature and high humidity conditions.
Also, the light resistance to long-term exposure was excellent.
【００３９】[0039]
【発明の効果】本発明のトリスアゾ化合物又はその塩は
染料系偏光膜として有用であり、該トリスアゾ化合物又
はその塩を用いた染料系偏光膜は、ヨウ素を用いた偏光
膜に匹敵する高い偏光性能を示し、又、耐久性と長時間
暴露に対する耐光性に優れるので、各種液晶表示体、な
かでも高い偏光性能と耐光性を必要とする液晶プロジェ
クター用途に好適である。The trisazo compound of the present invention or a salt thereof is useful as a dye-based polarizing film, and a dye-based polarizing film using the trisazo compound or a salt thereof has high polarization performance comparable to a polarizing film using iodine. And is excellent in durability and light resistance to long-term exposure, so that it is suitable for various liquid crystal displays, especially for liquid crystal projector applications requiring high polarization performance and light resistance.
───────────────────────────────────────────────────── フロントページの続き Ｆターム(参考） 2H049 BA02 BA30 BB43 BC02 BC22 4F071 AA29 AC14 AE09 AF35 AF57 AH19 BC01 4J002 BE021 EV236 FD096 GP00 ──────────────────────────────────────────────────続 き Continued on the front page F term (reference) 2H049 BA02 BA30 BB43 BC02 BC22 4F071 AA29 AC14 AE09 AF35 AF57 AH19 BC01 4J002 BE021 EV236 FD096 GP00
Claims (4)
表し、Ｒ1、Ｒ2、Ｒ3及びＲ4は、同一又は相異なり、水
素又は低級アルキルを表す。）で示されるトリスアゾ化
合物又はその塩。(1) The following formula (I): (Wherein, A represents naphthyl having 1 to 3 sulfo groups, and R 1 , R 2 , R 3 and R 4 are the same or different and represent hydrogen or lower alkyl). A compound or a salt thereof.
メチルである請求項１に記載のトリスアゾ化合物又はそ
の塩。2. The trisazo compound or a salt thereof according to claim 1, wherein R 1 to R 4 are the same or different and are hydrogen or methyl.
又はその塩を偏光膜基材に含有してなる染料系偏光膜。3. A dye-based polarizing film comprising the trisazo compound according to claim 1 or a salt thereof in a polarizing film substrate.
樹脂からなるフィルムである請求項３に記載の染料系偏
光膜。4. The dye-based polarizing film according to claim 3, wherein the polarizing film base is a film made of a polyvinyl alcohol-based resin.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2000357358A JP2002155218A (en) | 2000-11-24 | 2000-11-24 | Tris-azo compound or its salt and polarizing dye membrane including the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2000357358A JP2002155218A (en) | 2000-11-24 | 2000-11-24 | Tris-azo compound or its salt and polarizing dye membrane including the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2002155218A true JP2002155218A (en) | 2002-05-28 |
Family
ID=18829441
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000357358A Pending JP2002155218A (en) | 2000-11-24 | 2000-11-24 | Tris-azo compound or its salt and polarizing dye membrane including the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2002155218A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005290055A (en) * | 2004-03-31 | 2005-10-20 | Sumitomo Chemical Co Ltd | Polyazo compound or its salt and dye-based polarizing film containing the same |
| WO2006070818A1 (en) * | 2004-12-27 | 2006-07-06 | Mitsubishi Chemical Corporation | Trisazo dye, composition containing the same for anisotropic dye film, anisotropic dye film, and polarizing element |
| WO2013008735A1 (en) * | 2011-07-08 | 2013-01-17 | 日本化薬株式会社 | Polarizing element and polarizing plate |
| WO2020027021A1 (en) * | 2018-07-31 | 2020-02-06 | 三菱ケミカル株式会社 | Polyvinyl alcohol-based film and polarizing film |
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|---|---|---|---|---|
| JP2005290055A (en) * | 2004-03-31 | 2005-10-20 | Sumitomo Chemical Co Ltd | Polyazo compound or its salt and dye-based polarizing film containing the same |
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| WO2013008735A1 (en) * | 2011-07-08 | 2013-01-17 | 日本化薬株式会社 | Polarizing element and polarizing plate |
| JPWO2013008735A1 (en) * | 2011-07-08 | 2015-02-23 | 日本化薬株式会社 | Polarizing element and polarizing plate |
| WO2020027021A1 (en) * | 2018-07-31 | 2020-02-06 | 三菱ケミカル株式会社 | Polyvinyl alcohol-based film and polarizing film |
| CN112262177A (en) * | 2018-07-31 | 2021-01-22 | 三菱化学株式会社 | Polyvinyl alcohol film and polarizing film |
| JPWO2020027021A1 (en) * | 2018-07-31 | 2021-08-02 | 三菱ケミカル株式会社 | Polyvinyl alcohol film and polarizing film |
| CN112262177B (en) * | 2018-07-31 | 2023-08-22 | 三菱化学株式会社 | Polyvinyl alcohol film and polarizing film |
| JP7396045B2 (en) | 2018-07-31 | 2023-12-12 | 三菱ケミカル株式会社 | Polyvinyl alcohol film and polarizing film |
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