JP2009217012A - Polypropylene polarizing plate - Google Patents
Polypropylene polarizing plate Download PDFInfo
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- JP2009217012A JP2009217012A JP2008061125A JP2008061125A JP2009217012A JP 2009217012 A JP2009217012 A JP 2009217012A JP 2008061125 A JP2008061125 A JP 2008061125A JP 2008061125 A JP2008061125 A JP 2008061125A JP 2009217012 A JP2009217012 A JP 2009217012A
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- polarizing plate
- polypropylene
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- dichroic dye
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- -1 Polypropylene Polymers 0.000 title claims abstract description 15
- 239000004743 Polypropylene Substances 0.000 title claims abstract description 15
- 229920001155 polypropylene Polymers 0.000 title claims abstract description 15
- 238000004519 manufacturing process Methods 0.000 claims abstract description 7
- 238000010438 heat treatment Methods 0.000 claims abstract description 4
- 239000000975 dye Substances 0.000 claims description 30
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 7
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 7
- 238000004898 kneading Methods 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 150000001336 alkenes Chemical class 0.000 claims description 2
- 239000000987 azo dye Substances 0.000 claims description 2
- 229920001400 block copolymer Polymers 0.000 claims description 2
- 229920001519 homopolymer Polymers 0.000 claims description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 2
- 229920005604 random copolymer Polymers 0.000 claims description 2
- 239000000049 pigment Substances 0.000 abstract description 4
- 239000000243 solution Substances 0.000 description 9
- 239000004372 Polyvinyl alcohol Substances 0.000 description 8
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 8
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 8
- 229920002451 polyvinyl alcohol Polymers 0.000 description 8
- 239000007787 solid Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- GFGBNISGCXRRGF-UHFFFAOYSA-N 6-butyl-1,3-benzothiazol-2-amine Chemical compound CCCCC1=CC=C2N=C(N)SC2=C1 GFGBNISGCXRRGF-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 3
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- RBRCCWBAMGPRSN-UHFFFAOYSA-N thieno[2,3-d][1,3]thiazole Chemical compound S1C=NC2=C1C=CS2 RBRCCWBAMGPRSN-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical group C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical group COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- VQTGUFBGYOIUFS-UHFFFAOYSA-N nitrosylsulfuric acid Chemical compound OS(=O)(=O)ON=O VQTGUFBGYOIUFS-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical group C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JFGQHAHJWJBOPD-UHFFFAOYSA-N 3-hydroxy-n-phenylnaphthalene-2-carboxamide Chemical compound OC1=CC2=CC=CC=C2C=C1C(=O)NC1=CC=CC=C1 JFGQHAHJWJBOPD-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical group CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- AJSINQAAKNYUDA-UHFFFAOYSA-M sodium;anilinomethanesulfonate Chemical compound [Na+].[O-]S(=O)(=O)CNC1=CC=CC=C1 AJSINQAAKNYUDA-UHFFFAOYSA-M 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Landscapes
- Polarising Elements (AREA)
- Shaping By String And By Release Of Stress In Plastics And The Like (AREA)
Abstract
Description
本発明は、ポリプロピレン系の偏光板の製法に関する。本明細書において、「偏光板」と呼ぶときには、偏光フィルムをも包含するものである。 The present invention relates to a method for producing a polypropylene-based polarizing plate. In this specification, the term “polarizing plate” includes a polarizing film.
近年、液晶ディスプイの普及にともない、様々な用途での利用が進められているが、耐久性という観点から、特に湿度や熱、光に対する耐久性への要請が高まっている。従来の液晶ディスプレイではヨウ素系偏光フィルムを使用していることから湿度に対する耐久性が低く、耐湿潤性、耐熱性を改善することで将来的に大きな需要が見込まれることから、耐久性、生産性に優れる二色性色素を用いた偏光フィルムの技術の確立が期待されている状況にある。現在、耐久性に優れた二色性色素を用いた偏光フィルム部品の生産技術の確立に向けた研究開発が国内外で進められている。
従来、偏光板は、透明性、ヨウ素等の親和性や延伸時における高い配向性に優れるポリビニルアルコールのフィルムを延伸することによって製造されている。ヨウ素を吸着させたポリビニルアルコールのフィルムを一軸延伸する事により、ヨウ素が延伸方向に配向し、偏光性能を持った偏光素子層が得られる。
また、特開２００２−４８９１８号公報は、二色性色素を含有するポリビニルアルコールの層を用いて偏光板を製造することを開示している。
Conventionally, a polarizing plate is produced by stretching a film of polyvinyl alcohol that is excellent in transparency, affinity for iodine, etc. and high orientation during stretching. By uniaxially stretching a polyvinyl alcohol film on which iodine is adsorbed, the polarizing element layer having polarizing performance is obtained by orienting iodine in the stretching direction.
Japanese Patent Application Laid-Open No. 2002-48918 discloses manufacturing a polarizing plate using a polyvinyl alcohol layer containing a dichroic dye.
しかし、従来、ポリビニルアルコールが水溶性であるので偏光板が耐湿潤性に劣るという欠点、使用できる二色性色素が限定されているという欠点などが存在した。 However, conventionally, since polyvinyl alcohol is water-soluble, there have been a drawback that the polarizing plate is inferior in wet resistance, and a dichroic dye that can be used is limited.
本発明の目的は、種々の二色性色素が使用でき、耐湿潤性に優れた偏光板を提供することにある。 An object of the present invention is to provide a polarizing plate which can use various dichroic dyes and has excellent wet resistance.
本発明は、ポリプロピレンに二色性色素を加熱下で練り込み、成形してシートとし、シートを延伸することを特徴とする偏光板の製法を提供する。 The present invention provides a method for producing a polarizing plate characterized by kneading a dichroic dye into polypropylene under heating, forming the sheet into a sheet, and stretching the sheet.
本発明によれば、偏光板を、疎水性のポリプロピレンを使用して製造する。
耐湿潤性に優れた偏光板や偏光フィルムを作製できる。従来は、水溶性のポリビニルアルコール（ＰＶＡ）を使用しているために、偏光フィルムは、高湿度の条件では使用できなかったが、疎水性のポリプロピレンを使用しているので、高湿度の環境下でも偏光板の使用が可能となる。
According to the present invention, the polarizing plate is manufactured using hydrophobic polypropylene.
A polarizing plate and a polarizing film having excellent wet resistance can be produced. Conventionally, since a water-soluble polyvinyl alcohol (PVA) is used, the polarizing film cannot be used under high humidity conditions. However, since hydrophobic polypropylene is used, the polarizing film can be used in a high humidity environment. However, it is possible to use a polarizing plate.
親水性基を持たない色素であれば、様々な種類の二色性色素が適用できる。従来は、二色性色素は、ポリビニルアルコール（ＰＶＡ）に相溶するように、親水性の色素に限定されていた。しかし、本発明によれば、油溶性の二色性色素を使用でき、二色性色素の選択肢が広がる。
プロピレンは、容易に塑性変形するので、偏光板の加工が容易である。
Various types of dichroic dyes can be applied as long as they do not have a hydrophilic group. Conventionally, dichroic dyes are limited to hydrophilic dyes so as to be compatible with polyvinyl alcohol (PVA). However, according to the present invention, oil-soluble dichroic dyes can be used, and the options for dichroic dyes are expanded.
Since propylene easily plastically deforms, the polarizing plate can be easily processed.
本発明においては、プロピレンを使用する。プロピレンは、プロピレンを単独重合したホモポリマー、プロピレンとエチレン等の他のオレフィン（特にα−オレフィン）とのブロックコポリマー、ランダムコポリマーなどのポリプロピレンであってよい。ポリプロピレンの融点は、１５０℃以上、特に１６０℃以上であってよい。
ポリプロピレンに二色性色素を練り込むには、ポリプロピレンを融点以上の温度（例えば、１８０℃以上、例えば１９０〜２４０℃）に加熱し、ポリプロピレンと二色性色素とを混合することによって行える。
In the present invention, propylene is used. The propylene may be a polypropylene such as a homopolymer obtained by homopolymerizing propylene, a block copolymer of propylene and another olefin such as ethylene (particularly an α-olefin), or a random copolymer. The melting point of polypropylene may be 150 ° C. or higher, particularly 160 ° C. or higher.
The kneading of the dichroic dye into polypropylene can be performed by heating the polypropylene to a temperature equal to or higher than the melting point (for example, 180 ° C. or higher, for example, 190 to 240 ° C.) and mixing the polypropylene and the dichroic dye.
二色性色素は、どのようなものであっても良い。二色性色素は、アゾ系色素であることが好ましい。アゾ基の数は２（すなわち、ジアゾ）または３（すなわち、トリアゾ）であることが好ましい。アゾ基とアゾ基の間に芳香族基（例えば、ベンゼン環、ナフタレン環）またはスチルベン基が存在することが好ましい。１つの末端には、ベンゾチアゾールまたはチエノチアゾールが存在することが好ましい。他の末端には、ジエチルアミノベンゼン基、アニソール基、またはベンゼン環が存在することが好ましい。本発明において、基（例えば、アニソール基およびベンゼン環）は、置換されていてもあるいはされていなくてもよい。 Any dichroic dye may be used. The dichroic dye is preferably an azo dye. The number of azo groups is preferably 2 (ie diazo) or 3 (ie triazo). It is preferable that an aromatic group (for example, a benzene ring or a naphthalene ring) or a stilbene group exists between the azo group and the azo group. It is preferred that benzothiazole or thienothiazole is present at one end. A diethylaminobenzene group, anisole group, or benzene ring is preferably present at the other end. In the present invention, groups (for example, anisole group and benzene ring) may or may not be substituted.
二色性色素の具体例は次のとおりである。場合によりその合成スキームも示す。
ベンゾチアゾール系色素（１）：
ベンゾチアゾール系色素（２）：
上記スキーム中、Ｒ、Ｒ１、Ｒ２およびＲ３のそれぞれは、同一または異なって、水素原子または炭素数１〜３０の炭化水素基であってよい。
Specific examples of the dichroic dye are as follows. In some cases, the synthesis scheme is also shown.
Benzothiazole dye (1):
Benzothiazole dye (2):
In the above scheme, each of R, R 1 , R 2 and R 3 may be the same or different and each may be a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms.
チエノチアゾール系色素（１）：
チエノチアゾール系色素（１）：
スキーム中、Ｅｔはエチル基である。
Thienothiazole pigment (1):
Thienothiazole pigment (1):
In the scheme, Et is an ethyl group.
スチルベン系色素：
次いで、ポリプロピレン／色素混合物をシートに成形する。成形方法としては、種々の成形法が可能であるが、プレス成形法が好ましい。得られたシートの厚さは、一般に、０．１〜２ｍｍである．
成形されたシートを延伸する。一般に、一軸方向に延伸を行う。延伸倍率は、一般に、２〜２０倍、特に３〜１０倍である。
こうして、偏光板または偏光フィルムが得られる。
The polypropylene / dye mixture is then formed into a sheet. Various molding methods can be used as the molding method, but a press molding method is preferable. The thickness of the obtained sheet is generally 0.1 to 2 mm.
The formed sheet is stretched. In general, stretching is performed in a uniaxial direction. The draw ratio is generally 2 to 20 times, in particular 3 to 10 times.
Thus, a polarizing plate or a polarizing film is obtained.
以下、実施例を示し、本発明を具体的に説明する。 Hereinafter, the present invention will be specifically described with reference to examples.
合成例１
ベンゾチアゾール系二色性色素の合成：
以下のようにして、二色性色素4aを合成した。
Synthesis of benzothiazole dichroic dyes:
The dichroic dye 4a was synthesized as follows.
2-アミノ-6-ブチルベンゾチアゾール(1)5ｇ（24.2mmol）を85％リン酸83ｍｌ中、80℃で加熱分散させた後、30℃まで冷却した。このリン酸溶液に40％硫酸水素ニトロシル9.2ｇ(29mmol)を30℃〜５℃で滴下し、ジアゾニウム溶液を得た。一方、4四つ口フラスコにアニリノメタンスルホン酸ソーダ20.9ｇ(100mmol)を氷水500 mlに溶解させ、５℃以下に冷却した。この水溶液中に、ジアゾニウム溶液を０〜５℃で、１時間かけて滴下した。滴下終了後、１時間攪拌し、飽和食塩水43 mlを加え、更に５分間攪拌した。析出した固体をろ過し、飽和食塩水で、洗浄して残ったウェットケーキ状の(2)を３％炭酸ナトリウム水溶液170 mlと15％水酸化ナトリウム水溶液40 mlの混合液に加え、90〜95℃に加熱し、１時間攪拌した。10℃以下まで冷却後、析出した固体をろ過した。固体を水洗し、50℃で真空乾燥することにより、黒色固体2-(4-アニリノアゾ）-6-ブチルベンチアゾール(3)を得た。この粗製品をアセトン100 ml中で、還流後熱時ろ過し、この操作を３回繰り返した。ろ液を濃縮乾固させ、オイル状のものを得た。これにヘキサン100 mlを加え、還流後熱時ろ過し、この操作を３回繰り返した。得られた固体をアミノクロマトグラフィー（展開溶媒；クロロホルム）で精製することによって、モノアゾアミノ中間体(3)を1.0ｇ(収率13.8％)で得た。 2-amino-6-butylbenzothiazole (1) (5 g, 24.2 mmol) was heated and dispersed at 83 ° C. in 83 ml of 85% phosphoric acid, and then cooled to 30 ° C. To this phosphoric acid solution, 9.2 g (29 mmol) of 40% nitrosyl hydrogen sulfate was added dropwise at 30 ° C. to 5 ° C. to obtain a diazonium solution. On the other hand, 20.9 g (100 mmol) of sodium anilinomethanesulfonate was dissolved in 500 ml of ice water in a four-necked flask and cooled to 5 ° C. or lower. In this aqueous solution, the diazonium solution was dripped at 0-5 degreeC over 1 hour. After completion of the dropwise addition, the mixture was stirred for 1 hour, added with 43 ml of saturated saline, and further stirred for 5 minutes. The precipitated solid was filtered, washed with saturated brine, and the wet cake-like (2) remaining after addition was added to a mixture of 170 ml of 3% aqueous sodium carbonate solution and 40 ml of 15% aqueous sodium hydroxide solution. Heated to ° C. and stirred for 1 hour. After cooling to 10 ° C. or lower, the precipitated solid was filtered. The solid was washed with water and vacuum dried at 50 ° C. to obtain a black solid 2- (4-anilinoazo) -6-butylbenchazole (3). This crude product was refluxed in 100 ml of acetone and heated, and this operation was repeated three times. The filtrate was concentrated to dryness to obtain an oily product. To this was added 100 ml of hexane, and after refluxing, it was filtered while hot, and this operation was repeated three times. The obtained solid was purified by amino chromatography (developing solvent; chloroform) to obtain 1.0 g (yield 13.8%) of monoazoamino intermediate (3).
次に、ナフトールＡＳ1.2ｇ(4.56mmol)をＤＭＦ20 mlに溶解させた溶液に、モノアゾアミノ中間体(3)１ｇ(3.22mmol) を40％硫酸水素ニトロシルでジアゾ化溶液を０〜５℃で、１時間かけて、滴下した。反応後、この溶液を５％水酸化ナトリウム溶液300 mlに加え、30分間攪拌後、ろ過した。得られた固体を水50 mlとメタノール70 mlで洗浄し、50℃にて真空乾燥した。この固体をシリカゲルクロマトグラフィー（展開溶媒；クロロホルム）で精製することによって、二色性色素4aを0.28ｇ得た。（収率15％） Next, in a solution of 1.2 g (4.56 mmol) of naphthol AS in 20 ml of DMF, 1 g (3.22 mmol) of the monoazoamino intermediate (3) was converted to a diazotized solution with 0% nitrosyl hydrogen sulfate at 0 to 5 ° C. It was added dropwise over 1 hour. After the reaction, this solution was added to 300 ml of 5% sodium hydroxide solution, stirred for 30 minutes and then filtered. The obtained solid was washed with 50 ml of water and 70 ml of methanol and dried in vacuo at 50 ° C. The solid was purified by silica gel chromatography (developing solvent; chloroform) to obtain 0.28 g of dichroic dye 4a. (Yield 15%)
4a :Yiled 15%. 1H NMR (CDCl3) δ (ppm): 0.97 (t, J = 7.2Hz, 3H), 1.37-1.45 (m, 2H), 1.64-1.74 (m, 2H), 2.77 (t, J= 7.2Hz, 2H), 7.17 (t, J = 7.2Hz, 1H), 7.36 (dd, J = 1.2 and 7.2Hz, 1H), 7.41 (t, J = 8.4Hz, 2H), 7.51 (dt, J = 1.2 and 8.3 Hz, 1H), 7.67-7.72 (m,2H), 7.77 (d, J = 7.8Hz, 1H), 7.82 (d, J = 7.8Hz, 2H), 7.87(d, J = 9.0Hz, 2H) ,8.07 (d,J=8.4Hz, 1H), 8.22 (d,J=9.0Hz, 2H),8.48 (d, J = 8.1 Hz, 1H),9.02 (s, 1H). IR(KBr)1676 cm-1.MALDI-TOF MS: m/z 585 (M+). Dec: 281 ℃. λmax (ε)(CHCl3): 558 nm (5.5x104). 4a: Yiled 15%. 1 H NMR (CDCl 3 ) δ (ppm): 0.97 (t, J = 7.2Hz, 3H), 1.37-1.45 (m, 2H), 1.64-1.74 (m, 2H), 2.77 ( t, J = 7.2Hz, 2H), 7.17 (t, J = 7.2Hz, 1H), 7.36 (dd, J = 1.2 and 7.2Hz, 1H), 7.41 (t, J = 8.4Hz, 2H), 7.51 ( dt, J = 1.2 and 8.3 Hz, 1H), 7.67-7.72 (m, 2H), 7.77 (d, J = 7.8Hz, 1H), 7.82 (d, J = 7.8Hz, 2H), 7.87 (d, J = 9.0Hz, 2H), 8.07 (d, J = 8.4Hz, 1H), 8.22 (d, J = 9.0Hz, 2H), 8.48 (d, J = 8.1 Hz, 1H), 9.02 (s, 1H). IR (KBr) 1676 cm -1 .MALDI-TOF MS: m / z 585 (M + ). Dec: 281 ° C. Λ max (ε) (CHCl 3 ): 558 nm (5.5x10 4 ).
二色性色素4aと同様にして、二色性色素4b〜4hを製造した。
4b:Yield 13%. 1H NMR (CDCl3) δ (ppm):0.92 (t, J = 7.2Hz, 3H), 1.31-1.43 (m, 4H), 1.63-1.77 (m, 2H), 2.77 (t, J= 7.8Hz, 2H), 7.17 (t, J = 7.2Hz, 1H), 7.36 (d, J = 8.0Hz, 1H), 7.41 (t, J = 8.0Hz, 2H), 7.51 (dt, J = 1.2 and 7.2 Hz, 1H), 7.69 (t, J = 7.2Hz ,2H), 7.77 (d, J = 8.0Hz, 1H), 7.82 (d, J = 8.0Hz, 2H), 7.86(d, J = 8.8Hz, 1H) ,8.07 (d,J=8.4Hz, 1H), 8.22 (d,J = 8.8Hz, 2H),8.48 (d, J = 8.0 Hz, 1H),9.02 (s,1H),11.4(s,1H). IR(KBr)1670 cm-1.MALDI-TOF MS: m/z 597 (M+). Dec: 268 ℃. λmax (ε)(CHCl3): 558 nm (5.4x104).
Dichroic dyes 4b to 4h were produced in the same manner as the dichroic dye 4a.
4b: Yield 13%. 1 H NMR (CDCl 3 ) δ (ppm): 0.92 (t, J = 7.2Hz, 3H), 1.31-1.43 (m, 4H), 1.63-1.77 (m, 2H), 2.77 ( t, J = 7.8Hz, 2H), 7.17 (t, J = 7.2Hz, 1H), 7.36 (d, J = 8.0Hz, 1H), 7.41 (t, J = 8.0Hz, 2H), 7.51 (dt, J = 1.2 and 7.2 Hz, 1H), 7.69 (t, J = 7.2Hz, 2H), 7.77 (d, J = 8.0Hz, 1H), 7.82 (d, J = 8.0Hz, 2H), 7.86 (d, J = 8.8Hz, 1H), 8.07 (d, J = 8.4Hz, 1H), 8.22 (d, J = 8.8Hz, 2H), 8.48 (d, J = 8.0 Hz, 1H), 9.02 (s, 1H) IR (KBr) 1670 cm -1 .MALDI-TOF MS: m / z 597 (M + ). Dec: 268 ° C. Λ max (ε) (CHCl 3 ): 558 nm (5.4 x10 4 ).
4c: Yield 15%. 1H NMR (CDCl3) δ (ppm):0.90 (t, J = 6.8Hz, 3H), 1.37-1.41 (m, 6H), 1.63-1.77 (m, 2H), 2.76 (t, J= 8.0Hz, 2H), 7.17 (t, J = 7.2Hz, 1H), 7.36 (d, J = 8.8Hz, 1H), 7.41 (t, J = 7.6Hz, 2H), 7.51 (dt, J = 1.2 and 7.6 Hz, 1H), 7.69 (t, J = 8.8Hz ,2H), 7.77 (d, J = 8.0Hz, 1H), 7.82 (d, J = 7.2Hz, 2H), 7.86(d, J = 8.8Hz, 1H) ,8.07 (d,J=8.4Hz, 1H), 8.22 (d,J = 8.4Hz, 2H),8.48 (d, J = 8.4 Hz, 1H),9.02 (s, 1H),11.40(s,1H). IR(KBr)1676 cm-1.MALDI-TOF MS: m/z 611 (M+). Dec: 252 ℃. λmax (ε)(CHCl3): 559 nm (5.2x104). 4c: Yield 15%. 1 H NMR (CDCl 3 ) δ (ppm): 0.90 (t, J = 6.8Hz, 3H), 1.37-1.41 (m, 6H), 1.63-1.77 (m, 2H), 2.76 ( t, J = 8.0Hz, 2H), 7.17 (t, J = 7.2Hz, 1H), 7.36 (d, J = 8.8Hz, 1H), 7.41 (t, J = 7.6Hz, 2H), 7.51 (dt, J = 1.2 and 7.6 Hz, 1H), 7.69 (t, J = 8.8Hz, 2H), 7.77 (d, J = 8.0Hz, 1H), 7.82 (d, J = 7.2Hz, 2H), 7.86 (d, J = 8.8Hz, 1H), 8.07 (d, J = 8.4Hz, 1H), 8.22 (d, J = 8.4Hz, 2H), 8.48 (d, J = 8.4 Hz, 1H), 9.02 (s, 1H) , 11.40 (s, 1H). IR (KBr) 1676 cm -1 .MALDI-TOF MS: m / z 611 (M + ). Dec: 252 ° C. Λ max (ε) (CHCl 3 ): 559 nm (5.2 x10 4 ).
4d: Yield 17%.1H NMR (CDCl3) δ (ppm): 0.89 (t, J = 7.0Hz, 3H), 1.25-1.41 (m, 8H), 1.66-1.73 (m, 2H), 2.77 (t, J= 7.6Hz, 2H), 7.17 (t, J = 7.2Hz, 1H), 7.36 (d, J = 8.0Hz, 1H), 7.41 (t, J = 8.0Hz, 2H), 7.51 (dt, J = 1.2 and 8.0 Hz, 1H), 7.69 (t, J = 8.0Hz ,2H), 7.77 (d, J = 8.0Hz, 1H), 7.82 (d, J = 8.0Hz, 2H), 7.87(d, J = 8.8Hz, 1H) ,8.08 (d,J=8.4Hz, 1H), 8.22 (d,J = 8.8Hz, 2H),8.49 (d, J = 8.8 Hz, 1H),9.03 (s, 1H),11.40(s,1H). IR(KBr)1676 cm-1.MALDI-TOF MS: m/z 626 (M+). Dec: 226 ℃. λmax (ε)(CHCl3): 555 nm (5.2x104). 4d: Yield 17%. 1 H NMR (CDCl 3 ) δ (ppm): 0.89 (t, J = 7.0Hz, 3H), 1.25-1.41 (m, 8H), 1.66-1.73 (m, 2H), 2.77 ( t, J = 7.6Hz, 2H), 7.17 (t, J = 7.2Hz, 1H), 7.36 (d, J = 8.0Hz, 1H), 7.41 (t, J = 8.0Hz, 2H), 7.51 (dt, J = 1.2 and 8.0 Hz, 1H), 7.69 (t, J = 8.0Hz, 2H), 7.77 (d, J = 8.0Hz, 1H), 7.82 (d, J = 8.0Hz, 2H), 7.87 (d, J = 8.8Hz, 1H), 8.08 (d, J = 8.4Hz, 1H), 8.22 (d, J = 8.8Hz, 2H), 8.49 (d, J = 8.8 Hz, 1H), 9.03 (s, 1H) , 11.40 (s, 1H) .IR (KBr) 1676 cm -1 .MALDI-TOF MS: m / z 626 (M + ). Dec: 226 ° C. Λ max (ε) (CHCl 3 ): 555 nm (5.2 x10 4 ).
4e:Yield 13%. 1H NMR (CDCl3) δ (ppm): 0.90 (t, J = 7.2Hz, 3H), 1.25-1.47 (m, 10H), 1.64-1.72 (m, 2H), 2.75 (t, J= 7.8Hz, 2H), 7.16 (t, J = 7.2Hz, 1H), 7.34 (d, J = 8.4Hz, 1H), 7.41 (t, J = 8.0Hz, 2H), 7.50 (dt, J = 1.2 and 7.1 Hz, 1H), 7.69 (t, J = 6.9Hz ,2H), 7.76 (d, J = 8.1Hz, 1H), 7.83 (d, J = 8.0Hz, 2H), 7.85(d, J = 8.8Hz, 1H) ,8.06 (d,J=9.0Hz, 1H), 8.21 (d,J = 8.7Hz, 2H),8.47 (d, J = 8.1Hz, 1H),9.00 (s, 1H),11.39(s,1H). IR(KBr)1676 cm-1.MALDI-TOF MS: m/z 640 (M+). Dec: 241 ℃. λmax (ε)(CHCl3): 560 nm (5.8x104). 4e: Yield 13%. 1 H NMR (CDCl 3 ) δ (ppm): 0.90 (t, J = 7.2Hz, 3H), 1.25-1.47 (m, 10H), 1.64-1.72 (m, 2H), 2.75 ( t, J = 7.8Hz, 2H), 7.16 (t, J = 7.2Hz, 1H), 7.34 (d, J = 8.4Hz, 1H), 7.41 (t, J = 8.0Hz, 2H), 7.50 (dt, J = 1.2 and 7.1 Hz, 1H), 7.69 (t, J = 6.9Hz, 2H), 7.76 (d, J = 8.1Hz, 1H), 7.83 (d, J = 8.0Hz, 2H), 7.85 (d, J = 8.8Hz, 1H), 8.06 (d, J = 9.0Hz, 1H), 8.21 (d, J = 8.7Hz, 2H), 8.47 (d, J = 8.1Hz, 1H), 9.00 (s, 1H) , 11.39 (s, 1H). IR (KBr) 1676 cm -1 .MALDI-TOF MS: m / z 640 (M + ). Dec: 241 ° C. Λ max (ε) (CHCl 3 ): 560 nm (5.8 x10 4 ).
4f: Yield 19%. 1H NMR (CDCl3) δ (ppm): 0.89 (t, J = 7.0Hz, 3H), 1.22-1.35 (m, 8H), 1.71 (t, J= 7.2Hz, 2H),2.77(t, J = 7.5Hz, 2H), 3.73(s, 1H), 4.00(s, 3H), 6.97 (dd, J = 1.1 and 7.5Hz, 1H), 7.02 (t, J = 6.3Hz, 1H), 7.13 (t, J = 6.9Hz, 1H), 7.37 (dd, J = 1.1 and 8.4 Hz, 1H), 7.51(t, J = 7.5Hz, 1H), 7.67-7.71 (m, 2H), 7.77 (dd, J = 1.1, 7.8Hz, 1H), 7.85(dd, J = 1.1 and 9.0Hz, 2H), 8.08(d, J = 8.4Hz, 1H) 8.23 (d,J=9.0Hz, 2H), 8.49 (d, J = 8.7Hz, 1H),8.62 (dd, J = 1.1 and 8.1 Hz, 1H),9.02 (s, 1H). 11.62(s, 1H). IR(KBr)1670 cm-1. MALDI-TOF MS: m/z 655 (M+). Dec: 258 ℃. λmax (ε)(CHCl3): 555nm (5.7x104). 4f: Yield 19%. 1 H NMR (CDCl 3 ) δ (ppm): 0.89 (t, J = 7.0Hz, 3H), 1.22-1.35 (m, 8H), 1.71 (t, J = 7.2Hz, 2H) , 2.77 (t, J = 7.5Hz, 2H), 3.73 (s, 1H), 4.00 (s, 3H), 6.97 (dd, J = 1.1 and 7.5Hz, 1H), 7.02 (t, J = 6.3Hz, 1H), 7.13 (t, J = 6.9Hz, 1H), 7.37 (dd, J = 1.1 and 8.4 Hz, 1H), 7.51 (t, J = 7.5Hz, 1H), 7.67-7.71 (m, 2H), 7.77 (dd, J = 1.1, 7.8Hz, 1H), 7.85 (dd, J = 1.1 and 9.0Hz, 2H), 8.08 (d, J = 8.4Hz, 1H) 8.23 (d, J = 9.0Hz, 2H) , 8.49 (d, J = 8.7Hz, 1H), 8.62 (dd, J = 1.1 and 8.1 Hz, 1H), 9.02 (s, 1H). 11.62 (s, 1H). IR (KBr) 1670 cm -1 . MALDI-TOF MS: m / z 655 (M + ). Dec: 258 ° C. Λ max (ε) (CHCl 3 ): 555 nm (5.7x10 4 ).
4g: Yield 23%. 1H NMR (CDCl3) δ (ppm): 0.89 (t, J = 6.7Hz, 3H), 1.23-1.36 (m, 8H), 1.71 (t, J= 6.4Hz, 2H), 2.77(t, J = 8.9Hz, 2H), 3.94(s, 3H), 4.08(s, 3H), 6.62 (s, 1H), 7.37 (d, J = 8.0Hz, 1H), 7.51 (t, J = 7.5Hz, 1H), 7.68-7.70 (m, 2H), 7.76 (dd, J = 1.1 and 7.2Hz, 1H), 7.84(d, J = 8.8Hz, 2H), 8.08(d, J = 8.4Hz, 1H), 8.22 (d, J = 8.8Hz, 2H), 8.48 (d, J = 8.4Hz, 1H), 8.69 (s, 1H) , 9.00 (s, 1H). 11.49(s, 1H). IR(KBr)1670 cm-1. MALDI-TOF MS: m/z 720 (M+). Dec: 227 ℃. λmax (ε)(CHCl3): 554nm (5.5x104). 4g: Yield 23%. 1 H NMR (CDCl 3 ) δ (ppm): 0.89 (t, J = 6.7Hz, 3H), 1.23-1.36 (m, 8H), 1.71 (t, J = 6.4Hz, 2H) , 2.77 (t, J = 8.9Hz, 2H), 3.94 (s, 3H), 4.08 (s, 3H), 6.62 (s, 1H), 7.37 (d, J = 8.0Hz, 1H), 7.51 (t, J = 7.5Hz, 1H), 7.68-7.70 (m, 2H), 7.76 (dd, J = 1.1 and 7.2Hz, 1H), 7.84 (d, J = 8.8Hz, 2H), 8.08 (d, J = 8.4 Hz, 1H), 8.22 (d, J = 8.8Hz, 2H), 8.48 (d, J = 8.4Hz, 1H), 8.69 (s, 1H), 9.00 (s, 1H). 11.49 (s, 1H). IR (KBr) 1670 cm -1 . MALDI-TOF MS: m / z 720 (M + ). Dec: 227 ° C. Λ max (ε) (CHCl 3 ): 554 nm (5.5x10 4 ).
4h: Yield 32%. 1H NMR (CDCl3) δ (ppm): 0.96 (t, J = 7.2Hz, 3H), 1.35-1.43 (m, 2H), 1.67 (q,J = 7.6Hz, 2H), 2.51 (s, 3H), 2.74 (t, J= 7.6Hz, 2H), 7.10 (t, J = 7.6Hz, 1H), 7.27-7.36 (m, 3H), 7.49 (t, J = 7.6Hz, 1H), 7.57 (s, 1H), 7.68 (t, J = 7.6Hz ,1H), 7.74 (d, J = 7.6 Hz, 1H), 7.80 (d, J = 8.0Hz, 2H), 8.03(d, J = 8.4Hz, 1H) ,8.17 (d,J=8.8Hz, 2H), 8.32 (d,J = 8.0Hz, 1H),8.45 (d, J = 8.4 Hz, 1H),9.00 (s, 1H),11.19(s,1H). IR(KBr)1683 cm-1. MALDI-TOF MS: m/z 598 (M+). Dec: 269 ℃. λmax (ε)(CHCl3): 558nm (5.6x104). 4h: Yield 32%. 1 H NMR (CDCl 3 ) δ (ppm): 0.96 (t, J = 7.2Hz, 3H), 1.35-1.43 (m, 2H), 1.67 (q, J = 7.6Hz, 2H) , 2.51 (s, 3H), 2.74 (t, J = 7.6Hz, 2H), 7.10 (t, J = 7.6Hz, 1H), 7.27-7.36 (m, 3H), 7.49 (t, J = 7.6Hz, 1H), 7.57 (s, 1H), 7.68 (t, J = 7.6Hz, 1H), 7.74 (d, J = 7.6 Hz, 1H), 7.80 (d, J = 8.0Hz, 2H), 8.03 (d, J = 8.4Hz, 1H), 8.17 (d, J = 8.8Hz, 2H), 8.32 (d, J = 8.0Hz, 1H), 8.45 (d, J = 8.4 Hz, 1H), 9.00 (s, 1H) , 11.19 (s, 1H). IR (KBr) 1683 cm -1 . MALDI-TOF MS: m / z 598 (M + ). Dec: 269 ° C. Λ max (ε) (CHCl 3 ): 558 nm (5.6x10 4 ).
実施例１
ポリプロピレン（アルドリッチ製452157（平均分子量127000〜54000））70ｇを200℃の加熱した混練り機に投入し、混練り後、上記二色性色素4を50ｍｇ加え、さらに１０分間混練りを行い、着色した塊状の樹脂6.5ｇを取り出した。この塊状の樹脂を10ｃｍ×10ｃｍ×400μｍの型に入れ、200℃、135kgf/cm2の条件でプレス成形して、フィルムを作製した。作製したフィルムを3ｃｍ×5ｃｍの大きさに切断し、90℃で５倍に延伸し、偏光フィルム（エドモンド製TECH-SPEC）で入射光の方向を制御した可視光分光光度計（島津製ＵＶ−３１００）を用いて、延伸したフィルムの二色性を測定した。結果を表１に示す。
Example 1
70 g of polypropylene (452157 made by Aldrich (average molecular weight 127000-54000)) is put into a kneading machine heated at 200 ° C., and after kneading, 50 mg of the above dichroic dye 4 is added and further kneaded for 10 minutes to be colored. 6.5 g of the lump-shaped resin thus taken out was taken out. This massive resin was put into a 10 cm × 10 cm × 400 μm mold and press-molded under the conditions of 200 ° C. and 135 kgf / cm 2 to produce a film. The produced film was cut to a size of 3cm x 5cm, stretched 5 times at 90 ° C, and the visible light spectrophotometer (Shimadzu UV-) controlled the direction of the incident light with a polarizing film (TECH-SPEC made by Edmond). 3100) was used to measure the dichroism of the stretched film. The results are shown in Table 1.
色素Ｉ：
本発明によれは、種々の二色性色素を使用して、耐久性（耐湿潤性、耐熱性）のある偏光板または偏光フィルムが得られる。 According to the present invention, a polarizing plate or a polarizing film having durability (wet resistance, heat resistance) can be obtained using various dichroic dyes.
Claims (4)
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2014095899A (en) * | 2012-11-07 | 2014-05-22 | Samsung Electronics Co Ltd | Polarizing film and display device |
| US20140339482A1 (en) * | 2013-05-14 | 2014-11-20 | Kyungpook National University Industry-Academic Cooperation Foundation | Composition for polarization film, polarization film, and display device |
| KR20160079447A (en) * | 2014-12-26 | 2016-07-06 | 삼성전자주식회사 | Composition for polarizing film and polarizing film and display device |
| US9442220B2 (en) | 2010-08-30 | 2016-09-13 | Samsung Electronics Co., Ltd. | Composition for polarizing film, polarizing film, method of manufacturing the same, and liquid crystal display provided with the polarizing film |
| JP2022028423A (en) * | 2020-08-03 | 2022-02-16 | 三菱ケミカル株式会社 | Anisotropic dye film-forming composition, anisotropic dye film, and optical element |
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| JPH04333002A (en) * | 1991-05-08 | 1992-11-20 | Mitsubishi Petrochem Co Ltd | Polarization film and manufacture thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JPH04333002A (en) * | 1991-05-08 | 1992-11-20 | Mitsubishi Petrochem Co Ltd | Polarization film and manufacture thereof |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9442220B2 (en) | 2010-08-30 | 2016-09-13 | Samsung Electronics Co., Ltd. | Composition for polarizing film, polarizing film, method of manufacturing the same, and liquid crystal display provided with the polarizing film |
| US9448335B2 (en) | 2010-08-30 | 2016-09-20 | Samsung Electronics Co., Ltd. | Composition for polarizing film, polarizing film, method of manufacturing the same, and liquid crystal display provided with the polarizing film |
| JP2014095899A (en) * | 2012-11-07 | 2014-05-22 | Samsung Electronics Co Ltd | Polarizing film and display device |
| JP2018112756A (en) * | 2012-11-07 | 2018-07-19 | 三星電子株式会社Ｓａｍｓｕｎｇ Ｅｌｅｃｔｒｏｎｉｃｓ Ｃｏ．，Ｌｔｄ． | Polarizing film and display device |
| US20140339482A1 (en) * | 2013-05-14 | 2014-11-20 | Kyungpook National University Industry-Academic Cooperation Foundation | Composition for polarization film, polarization film, and display device |
| US9798057B2 (en) | 2013-05-14 | 2017-10-24 | Samsung Electronics Co., Ltd. | Composition for polarization film, polarization film, and display device |
| KR102057722B1 (en) * | 2013-05-14 | 2019-12-19 | 삼성전자주식회사 | Composition for polarizing film and polarizing film and display device |
| KR20160079447A (en) * | 2014-12-26 | 2016-07-06 | 삼성전자주식회사 | Composition for polarizing film and polarizing film and display device |
| KR102392187B1 (en) | 2014-12-26 | 2022-04-28 | 삼성전자주식회사 | Composition for polarizing film and polarizing film and display device |
| JP2022028423A (en) * | 2020-08-03 | 2022-02-16 | 三菱ケミカル株式会社 | Anisotropic dye film-forming composition, anisotropic dye film, and optical element |
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