WO2011067959A1 - Coating liquid for forming polarizing film, and polarizing film - Google Patents
Coating liquid for forming polarizing film, and polarizing film Download PDFInfo
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- WO2011067959A1 WO2011067959A1 PCT/JP2010/061008 JP2010061008W WO2011067959A1 WO 2011067959 A1 WO2011067959 A1 WO 2011067959A1 JP 2010061008 W JP2010061008 W JP 2010061008W WO 2011067959 A1 WO2011067959 A1 WO 2011067959A1
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/30—Polarising elements
- G02B5/3025—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state
- G02B5/3033—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state in the form of a thin sheet or foil, e.g. Polaroid
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/02—Disazo dyes
- C09B31/08—Disazo dyes from a coupling component "C" containing directive hydroxyl and amino groups
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/41—Organic pigments; Organic dyes
Definitions
- the present invention suppresses a decrease in the degree of polarization and has a high degree of polarization even when drying according to the evaporation of the solvent.
- the present invention relates to a polarizing film generating coating liquid capable of generating a film and a polarizing film generated from a polarizing film generating coating liquid.
- the present invention has been made in order to solve the above-described conventional problems, and when a polarizing film is produced by casting a thin film to evaporate the solvent, even when drying according to the evaporation of the solvent, It is an object of the present invention to provide a polarizing film generating coating liquid capable of generating a polarizing film having a high degree of polarization while suppressing a decrease in the polarizing degree, and a polarizing film generated from the polarizing film generating coating liquid.
- a polarizing film generating coating liquid according to claim 1 contains an azo compound having an anionic group, a solvent for dissolving the azo compound, and an ionic liquid.
- the polarizing film according to claim 2 is obtained by casting the coating liquid for forming a polarizing film according to claim 1 into a thin film and evaporating the solvent.
- the azo compound is preferably contained in the polarizing film generating coating solution in a range of 0.5 wt% to 50 wt%.
- the azo compound is preferably a compound represented by the following chemical formula 1, as described in claim 4.
- M is a hydrogen atom, an alkali metal or ammonium compound
- R is a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, an acetyl group, a benzoyl group, a phenyl group, or a derivative group thereof
- X is a hydrogen atom, halogen
- An atom, a nitro group, a cyano group, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a —SO 3 M group is represented.
- the ionic liquid is preferably contained in the range of 1 to 15 parts by weight with respect to 100 parts by weight of the total solid content.
- the ionic liquid may be selected from 1-butyl-3-methylimidazolium salt, 1-ethyl-3-methylimidazolium salt, or a mixture thereof as described in claim 6. preferable.
- the polarizing film generating coating liquid according to the present invention when the polarizing film is produced by casting in a thin film to evaporate the solvent, the degree of polarization decreases even when drying is performed according to evaporation of the solvent. And a polarizing film having a high degree of polarization can be generated.
- the present inventors and others have intensively studied that the polarizing film generation coating liquid according to the present invention can generate a polarizing film having a high degree of polarization while suppressing a decrease in the degree of polarization. It is presumed as follows that the mechanism is expressed.
- a polarizing film is generated from a conventional coating liquid for generating a polarizing film as described above will be described with reference to FIG. 1A.
- the polarizing film generating coating solution was cast into a thin film on a glass plate or a resin film, the azo compound AZ and the solvent molecule SV were used in the thin polarizing film generating coating solution as shown in the left figure. Exists in a random state.
- the volume of the coating film decreases as the solvent evaporates, and the azo compound AZ is regularly oriented as shown in the center figure. It becomes. In this state, the degree of orientation of the azo compound AZ is the largest.
- the azo compounds AZ are tilted and oriented in order to relieve stress between molecules of the azo compound AZ. As a result, the degree of orientation of the azo compound is lowered.
- FIG. 1B a case where a polarizing film is generated from the polarizing film generating coating liquid according to the present invention will be described with reference to FIG. 1B.
- the polarizing film generating coating solution was cast into a thin film on a glass plate or a resin film, the azo compound AZ and the solvent molecule SV were used in the thin polarizing film generating coating solution as shown in the left figure.
- the ionic liquid IL exists in a random state.
- the volume of the coating film decreases as the solvent evaporates, and the azo compound AZ is regularly oriented as shown in the center figure. It becomes. In this state, the degree of orientation of the azo compound AZ is the largest.
- the interval between the azo compounds AZ becomes smaller at a certain point, but as shown in the figure on the right side, there is an ionic liquid IL between the molecules of the azo compound AZ.
- the azo compounds AZ are not too close to each other even when the solvent evaporates. From this, the orientation of the azo compounds AZ is maintained without being disturbed, and the degree of orientation is lowered. There is nothing.
- the coating liquid for generating a polarizing film according to the present invention by containing the ionic liquid in addition to the azo compound and the solvent, it is possible to prevent the polarization degree of the generated polarizing film from being lowered.
- the “ionic liquid” is a liquid containing an organic salt that does not crystallize even at room temperature, and has a characteristic that the cation size is large and asymmetric. For this reason, when an ionic liquid is mixed in the coating liquid for forming a polarizing film of the present invention, the cation of the ionic liquid forms an ion pair with a part of the azo compound having an anionic group. It is considered that the orientation of the azo compound molecules can be maintained in one direction in order to appropriately widen the molecular spacing.
- generation coating liquid which concerns on this invention is demonstrated based on embodiment.
- the polarizing film generating coating liquid of the present embodiment includes an azo compound having an anionic group, a solvent for dissolving the azo compound, and an ionic liquid.
- Such a coating liquid preferably exhibits liquid crystallinity when the concentration of the azo compound is in the range of 0.5 wt% to 50 wt%.
- generation may contain the other compound and additive, as long as there exists the said effect.
- the ionic liquid used in the coating liquid for producing a polarizing film of this embodiment is a liquid containing an organic salt that does not crystallize even at room temperature (for example, 20 ° C. to 40 ° C.).
- the ionic liquid is typically a salt of a cation of a cyclic compound containing nitrogen such as imidazole or triazole and an anion such as phosphorus hexafluoride or sulfonic imide.
- 1-butyl-3-methylimidazolium salt, 1-ethyl-3-methylimidazolium salt, or a mixture thereof is preferable because of its excellent solubility in a hydrophilic solvent.
- These ionic liquids are available from, for example, Nippon Synthetic Chemical Company or ALDRICH.
- the mixing amount of the ionic liquid to the polarizing film forming coating liquid is preferably 1 to 15 parts by weight with respect to 100 parts by weight of the total solid content. If the mixing amount of the ionic liquid is less than 1 part by weight, the effect of suppressing the decrease in the degree of polarization may be reduced during the drying process. If it exceeds 15 parts by weight, the orientation of the azo compound is disturbed, and the polarization There is a risk that the degree will decrease.
- the azo compound used in the coating liquid for producing a polarizing film of this embodiment has an anionic group.
- the anionic group include —SO 3 M, —COOM, —PO 3 MH, —PO 3 M 2 and the like.
- M is a hydrogen atom, an alkali metal, or an ammonium compound.
- the azo compound is preferably a compound represented by the following chemical formula 1. Such a compound exhibits good orientation and exhibits absorption dichroism in the visible light region (wavelength 380 nm to 780 nm).
- M is a hydrogen atom, an alkali metal, or an ammonium compound as described above
- R is a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, an acetyl group, a benzoyl group, a phenyl group, or a derivative group thereof.
- X represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or an —SO 3 M group.
- the azo compound can be obtained, for example, by subjecting an aniline derivative and a naphthalene derivative to diazotization and coupling reaction by a conventional method to obtain a monoazo compound, followed by further diazotization and coupling reaction with a 1-amino-8-naphthol derivative. be able to.
- the solvent used in the coating liquid for forming a polarizing film of this embodiment is one that dissolves an azo compound, and preferably a hydrophilic solvent is used.
- the hydrophilic solvent is preferably water, alcohols, cellosolves or a mixed solvent thereof.
- the polarizing film according to this embodiment is obtained by flowing the coating liquid into a book film and evaporating the solvent.
- the thickness of the polarizing film is preferably 0.1 ⁇ m or more and less than 10 ⁇ m.
- the court means is not particularly limited as long as the coating liquid can be uniformly cast, and an appropriate coater such as a slide coater, a slot die coater, a bar coater, or the like is used.
- As the drying method for example, natural drying, reduced pressure drying, heat drying or the like is used.
- the drying temperature is preferably 50 ° C to 120 ° C.
- the concentration of the azo compound in the coating liquid for producing a polarizing film is 9% by weight, and the mixing amount of the ionic liquid is 2 parts by weight with respect to 100 parts by weight of the total solid content of the coating liquid for producing a polarizing film. .
- This polarizing film-generating coating solution is cast into a thin film using a bar coater (manufactured by BUSHMAN) on a cycloolefin resin film (manufactured by Nippon Zeon Co., Ltd., trade name “ZEONOR”) to evaporate moisture. Then, a polarizing film having a thickness of 0.2 ⁇ m was produced on the cycloolefin-based resin film.
- FIG. 2 shows a change in polarization degree (graph) in the drying process until moisture is evaporated from the coating liquid and a polarizing film is formed.
- a polarizing film producing coating solution was prepared in the same manner as in Example 1 except that 1-ethyl-3-methylpyridinium ethyl sulfate (manufactured by Tokyo Chemical Industry Co., Ltd.) was used as the ionic liquid. Produced.
- 1-ethyl-3-methylpyridinium ethyl sulfate manufactured by Tokyo Chemical Industry Co., Ltd.
- the graph shown in FIG. 2 was obtained as in the case of Example 1.
- FIG. 3 shows a change in polarization degree (graph) in the drying process until moisture is evaporated from the polarizing film-generating coating liquid and a light-repelling film is generated.
- the horizontal axis represents the drying time (sec), and the vertical axis represents the degree of polarization.
- the degree of polarization was the highest when the drying time was around 80 seconds, and the high degree of polarization (98.3%) was maintained as it was thereafter.
- the degree of polarization of the polarizing film shows a maximum value (98%) at a drying time of about 80 seconds, and thereafter the degree of polarization is increased. Decreased by about 1%.
- the present invention suppresses a decrease in the degree of polarization and has a high degree of polarization even when drying according to the evaporation of the solvent.
- a polarizing film generating coating liquid capable of generating a film and a polarizing film generated from the polarizing film generating coating liquid can be provided, and the effect exerted industrially is great.
Abstract
Disclosed is a coating liquid for forming a polarizing film, which is characterized by containing an azo compound that has an anionic group, a solvent that dissolves the azo compound, and an ionic liquid.
Description
本発明は、薄膜状に流延して溶媒を蒸発させて偏光膜を生成する際に、溶媒の蒸発に従って乾燥していく場合においても、偏光度の低下を抑制して高い偏光度を有する偏光膜を生成可能な偏光膜生成用コーティング液及び偏光膜生成用コーティング液から生成される偏光膜に関するものである。
In the case of producing a polarizing film by casting a thin film and evaporating the solvent, the present invention suppresses a decrease in the degree of polarization and has a high degree of polarization even when drying according to the evaporation of the solvent. The present invention relates to a polarizing film generating coating liquid capable of generating a film and a polarizing film generated from a polarizing film generating coating liquid.
従来より、特開２００９－１７３８４９号公報に記載されているように、陰イオン性置換基を有するアゾ化合物とアゾ化合物を溶解する溶媒を含む液晶性コーティング液が知られている。このような液晶性コーティング液を乾燥して得られる偏光膜は、ポリビニルアルコールフィルムを延伸染色して得られる汎用の偏光膜に比べて、厚みを格段に薄くできるため、将来期待されている。
特開２００９－１７３８４９号公報
Conventionally, as described in JP-A-2009-173849, a liquid crystalline coating solution containing an azo compound having an anionic substituent and a solvent for dissolving the azo compound is known. A polarizing film obtained by drying such a liquid crystalline coating liquid is expected in the future because it can be made much thinner than a general-purpose polarizing film obtained by stretching and staining a polyvinyl alcohol film.
JP 2009-173849 A
しかしながら、前記特許文献１に記載された液晶性コーティング液をガラス板や樹脂フィルム上に流延し、溶媒を蒸発させて偏光膜を生成する場合、溶媒が蒸発して乾燥が進むに従って偏光度が上昇していき、所定の時間が経過した時点で偏光度は最高値を示すものの、その後乾燥が進むに従って偏光度が数パーセント低下してしまうという課題がある。
However, when the liquid crystalline coating liquid described in Patent Document 1 is cast on a glass plate or a resin film and the solvent is evaporated to form a polarizing film, the degree of polarization increases as the solvent evaporates and drying proceeds. Although the degree of polarization reaches its maximum value when the predetermined time elapses, there is a problem that the degree of polarization decreases by several percent as drying proceeds thereafter.
本発明は前記従来における課題を解決するためになされたものであり、薄膜状に流延して溶媒を蒸発させて偏光膜を生成する際に、溶媒の蒸発に従って乾燥していく場合においても、偏光度の低下を抑制して高い偏光度を有する偏光膜を生成可能な偏光膜生成用コーティング液及びその偏光膜生成用コーティング液から生成される偏光膜を提供することを目的とする。
The present invention has been made in order to solve the above-described conventional problems, and when a polarizing film is produced by casting a thin film to evaporate the solvent, even when drying according to the evaporation of the solvent, It is an object of the present invention to provide a polarizing film generating coating liquid capable of generating a polarizing film having a high degree of polarization while suppressing a decrease in the polarizing degree, and a polarizing film generated from the polarizing film generating coating liquid.
前記目的を達成するため請求項１に係る偏光膜生成用コーティング液は、陰イオン性基を有するアゾ化合物と、前記アゾ化合物を溶解する溶媒と、イオン性液体とを含有することを特徴とする。
In order to achieve the above object, a polarizing film generating coating liquid according to claim 1 contains an azo compound having an anionic group, a solvent for dissolving the azo compound, and an ionic liquid. .
また、請求項２に係る偏光膜は、請求項１に記載の偏光膜生成用コーティング液を薄膜状に流延し溶媒を蒸発させて得られる。
ここに、前記アゾ化合物は、請求項３に記載されているように、０．５重量％～５０重量％の範囲で前記偏光膜生成用コーティング液に含有されていることが好ましい。
また、前記アゾ化合物は、請求項４に記載されているように、下記化１で表わされる化合物であることが好ましい。
化１中、Ｍは水素原子、アルカリ金属又はアンモニウム化合物、Ｒは水素原子、炭素数１～３のアルキル基、アセチル基、ベンゾイル基、フェニル基、又はそれらの誘導体基、Ｘは水素原子、ハロゲン原子、ニトロ基、シアノ基、炭素数１～４のアルキル基、炭素数１～４のアルコキシ基又は－ＳＯ3Ｍ基をそれぞれ表す。
更に、前記イオン性液体は、請求項５に記載されているように、全固形分１００重量部に対して１重量部～１５重量部の範囲で含有されていることが好ましい。
また、前記イオン性液体は、請求項６に記載されているように、１－ブチル－３－メチルイミダゾリウム塩、１－エチル－３－メチルイミダゾリウム塩又はこれらの混合物から選択されることが好ましい。 The polarizing film according to claim 2 is obtained by casting the coating liquid for forming a polarizing film according to claim 1 into a thin film and evaporating the solvent.
Here, as described in claim 3, the azo compound is preferably contained in the polarizing film generating coating solution in a range of 0.5 wt% to 50 wt%.
The azo compound is preferably a compound represented by the followingchemical formula 1, as described in claim 4.
In formula 1, M is a hydrogen atom, an alkali metal or ammonium compound, R is a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, an acetyl group, a benzoyl group, a phenyl group, or a derivative group thereof, X is a hydrogen atom, halogen An atom, a nitro group, a cyano group, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a —SO 3 M group is represented.
Further, as described in claim 5, the ionic liquid is preferably contained in the range of 1 to 15 parts by weight with respect to 100 parts by weight of the total solid content.
The ionic liquid may be selected from 1-butyl-3-methylimidazolium salt, 1-ethyl-3-methylimidazolium salt, or a mixture thereof as described in claim 6. preferable.
ここに、前記アゾ化合物は、請求項３に記載されているように、０．５重量％～５０重量％の範囲で前記偏光膜生成用コーティング液に含有されていることが好ましい。
また、前記アゾ化合物は、請求項４に記載されているように、下記化１で表わされる化合物であることが好ましい。
更に、前記イオン性液体は、請求項５に記載されているように、全固形分１００重量部に対して１重量部～１５重量部の範囲で含有されていることが好ましい。
また、前記イオン性液体は、請求項６に記載されているように、１－ブチル－３－メチルイミダゾリウム塩、１－エチル－３－メチルイミダゾリウム塩又はこれらの混合物から選択されることが好ましい。 The polarizing film according to claim 2 is obtained by casting the coating liquid for forming a polarizing film according to claim 1 into a thin film and evaporating the solvent.
Here, as described in claim 3, the azo compound is preferably contained in the polarizing film generating coating solution in a range of 0.5 wt% to 50 wt%.
The azo compound is preferably a compound represented by the following
Further, as described in claim 5, the ionic liquid is preferably contained in the range of 1 to 15 parts by weight with respect to 100 parts by weight of the total solid content.
The ionic liquid may be selected from 1-butyl-3-methylimidazolium salt, 1-ethyl-3-methylimidazolium salt, or a mixture thereof as described in claim 6. preferable.
本発明に係る偏光膜生成用コーティング液によれば、薄膜状に流延して溶媒を蒸発させて偏光膜を生成する際に、溶媒の蒸発に従って乾燥していく場合においても、偏光度の低下を抑制して高い偏光度を有する偏光膜を生成することができる。
According to the polarizing film generating coating liquid according to the present invention, when the polarizing film is produced by casting in a thin film to evaporate the solvent, the degree of polarization decreases even when drying is performed according to evaporation of the solvent. And a polarizing film having a high degree of polarization can be generated.
ここで、本発明に係る偏光膜生成用コーティング液により、偏光度の低下を抑制して高い偏光度を有する偏光膜を生成することができることに関して、本発明者等が鋭意検討したところ、かかる効果が発現するメカニズムとして以下のように推察される。
Here, the present inventors and others have intensively studied that the polarizing film generation coating liquid according to the present invention can generate a polarizing film having a high degree of polarization while suppressing a decrease in the degree of polarization. It is presumed as follows that the mechanism is expressed.
先ず、前記したように従来の偏光膜生成用コーティング液から偏光膜を生成する場合について図１Ａに基づき説明する。偏光膜生成用コーティング液をガラス板や樹脂フィルムに薄膜状に流延した当初においては、左側の図に示すように、薄膜状の偏光膜生成用コーティング液中で、アゾ化合物ＡＺ、溶媒分子ＳＶはランダム状態で存在している。
First, a case where a polarizing film is generated from a conventional coating liquid for generating a polarizing film as described above will be described with reference to FIG. 1A. At the beginning, when the polarizing film generating coating solution was cast into a thin film on a glass plate or a resin film, the azo compound AZ and the solvent molecule SV were used in the thin polarizing film generating coating solution as shown in the left figure. Exists in a random state.
薄膜状の偏光膜生成用コーティング液から溶媒が蒸発していくと、溶媒が蒸発するにつれて塗膜の体積が減少し、中央の図に示すように、アゾ化合物ＡＺは規則的に配向された状態となる。この状態でアゾ化合物ＡＺの配向度はもっとも大きくなる。
As the solvent evaporates from the coating liquid for forming a thin polarizing film, the volume of the coating film decreases as the solvent evaporates, and the azo compound AZ is regularly oriented as shown in the center figure. It becomes. In this state, the degree of orientation of the azo compound AZ is the largest.
更に溶媒が蒸発していくと、ある時点でアゾ化合物ＡＺ相互間の間隔が小さくなり過ぎ過密状態となる。そして、右側の図に示すように、アゾ化合物ＡＺの分子間のストレスを緩和するために、アゾ化合物ＡＺ相互が傾いて配向する。これに起因して、アゾ化合物の配向度は低下してしまう。
Further, when the solvent further evaporates, the interval between the azo compounds AZ becomes too small at a certain point in time, resulting in an overcrowded state. Then, as shown in the diagram on the right side, the azo compounds AZ are tilted and oriented in order to relieve stress between molecules of the azo compound AZ. As a result, the degree of orientation of the azo compound is lowered.
次に、本発明に係る偏光膜生成用コーティング液から偏光膜を生成する場合について図１Ｂに基づき説明する。偏光膜生成用コーティング液をガラス板や樹脂フィルムに薄膜状に流延した当初においては、左側の図に示すように、薄膜状の偏光膜生成用コーティング液中で、アゾ化合物ＡＺ、溶媒分子ＳＶ及びイオン性液体ＩＬはランダム状態で存在している。
Next, a case where a polarizing film is generated from the polarizing film generating coating liquid according to the present invention will be described with reference to FIG. 1B. At the beginning, when the polarizing film generating coating solution was cast into a thin film on a glass plate or a resin film, the azo compound AZ and the solvent molecule SV were used in the thin polarizing film generating coating solution as shown in the left figure. The ionic liquid IL exists in a random state.
薄膜状の偏光膜生成用コーティング液から溶媒が蒸発していくと、溶媒が蒸発するにつれて塗膜の体積が減少し、中央の図に示すように、アゾ化合物ＡＺは規則的に配向された状態となる。この状態でアゾ化合物ＡＺの配向度はもっとも大きくなる。
As the solvent evaporates from the coating liquid for forming a thin polarizing film, the volume of the coating film decreases as the solvent evaporates, and the azo compound AZ is regularly oriented as shown in the center figure. It becomes. In this state, the degree of orientation of the azo compound AZ is the largest.
更に溶媒が蒸発していくと、ある時点でアゾ化合物ＡＺ相互間の間隔が小さくなっていくが、右側の図に示すように、アゾ化合物ＡＺの分子間には、イオン性液体ＩＬが存在してアゾ化合物分子ＡＺ相互の間隔を広げることから、溶媒が蒸発しても各アゾ化合物ＡＺ同士が近接し過ぎることはなく、これよりアゾ化合物ＡＺの配向は乱れることなく維持され配向度が低下することはない。
As the solvent further evaporates, the interval between the azo compounds AZ becomes smaller at a certain point, but as shown in the figure on the right side, there is an ionic liquid IL between the molecules of the azo compound AZ. As the distance between the azo compound molecules AZ is increased, the azo compounds AZ are not too close to each other even when the solvent evaporates. From this, the orientation of the azo compounds AZ is maintained without being disturbed, and the degree of orientation is lowered. There is nothing.
このように、本発明に係る偏光膜生成用コーティング液では、アゾ化合物と溶媒に加えて、イオン性液体を含むことにより、生成される偏光膜の偏光度が低下することを防ぐことができる。
As described above, in the coating liquid for generating a polarizing film according to the present invention, by containing the ionic liquid in addition to the azo compound and the solvent, it is possible to prevent the polarization degree of the generated polarizing film from being lowered.
ここに、「イオン性液体」とは、常温でも結晶化しない有機塩を含む液体であり、陽イオンサイズが大きく非対称であるという特徴を有する。このため、本発明の偏光膜生成用コーティング液中に、イオン性液体を混合すると、イオン性液体の陽イオンが、陰イオン性基を有するアゾ化合物の一部とイオン対を形成し、アゾ化合物の分子間隔を適度に広げるため、アゾ化合物分子の配向を一方向に維持できると考えられる。
Here, the “ionic liquid” is a liquid containing an organic salt that does not crystallize even at room temperature, and has a characteristic that the cation size is large and asymmetric. For this reason, when an ionic liquid is mixed in the coating liquid for forming a polarizing film of the present invention, the cation of the ionic liquid forms an ion pair with a part of the azo compound having an anionic group. It is considered that the orientation of the azo compound molecules can be maintained in one direction in order to appropriately widen the molecular spacing.
因みに、単に分子サイズの大きい化合物（イオン性液体でないもの／常温で固体）を用いた場合、混合した化合物が凝集してアゾ化合物の配向を阻害したり、偏光膜の表面に析出して光学的欠点となったりして、前記した本発明の効果は得られない。
By the way, when a compound with a large molecular size (non-ionic liquid / solid at room temperature) is used, the mixed compound aggregates to inhibit the orientation of the azo compound, or precipitates on the surface of the polarizing film and becomes optical. The above-described effects of the present invention cannot be obtained due to disadvantages.
ＡＺ アゾ化合物
ＳＶ 溶媒分子
ＩＬ イオン性液体 AZ Azo compound SV Solvent molecule IL Ionic liquid
ＳＶ 溶媒分子
ＩＬ イオン性液体 AZ Azo compound SV Solvent molecule IL Ionic liquid
以下、本発明に係る偏光膜生成用コーティング液について、実施形態に基づき説明する。
［偏光膜生成用コーティング液］
本実施形態の偏光膜生成用コーティング液は、陰イオン性基を有するアゾ化合物と、アゾ化合物を溶解する溶媒と、イオン性液体とを含む。
かかるコーティング液は、好ましくはアゾ化合物の濃度が０．５重量％～５０重量％の範囲で、液晶性を示す。
尚、偏光膜生成用コーティング液は、上記効果を奏する限りにおいて、他の化合物や添加剤を含有していてもよい。 Hereinafter, the polarizing film production | generation coating liquid which concerns on this invention is demonstrated based on embodiment.
[Coating liquid for polarizing film production]
The polarizing film generating coating liquid of the present embodiment includes an azo compound having an anionic group, a solvent for dissolving the azo compound, and an ionic liquid.
Such a coating liquid preferably exhibits liquid crystallinity when the concentration of the azo compound is in the range of 0.5 wt% to 50 wt%.
In addition, the coating liquid for polarizing film production | generation may contain the other compound and additive, as long as there exists the said effect.
［偏光膜生成用コーティング液］
本実施形態の偏光膜生成用コーティング液は、陰イオン性基を有するアゾ化合物と、アゾ化合物を溶解する溶媒と、イオン性液体とを含む。
かかるコーティング液は、好ましくはアゾ化合物の濃度が０．５重量％～５０重量％の範囲で、液晶性を示す。
尚、偏光膜生成用コーティング液は、上記効果を奏する限りにおいて、他の化合物や添加剤を含有していてもよい。 Hereinafter, the polarizing film production | generation coating liquid which concerns on this invention is demonstrated based on embodiment.
[Coating liquid for polarizing film production]
The polarizing film generating coating liquid of the present embodiment includes an azo compound having an anionic group, a solvent for dissolving the azo compound, and an ionic liquid.
Such a coating liquid preferably exhibits liquid crystallinity when the concentration of the azo compound is in the range of 0.5 wt% to 50 wt%.
In addition, the coating liquid for polarizing film production | generation may contain the other compound and additive, as long as there exists the said effect.
［イオン性液体］
本実施形態の偏光膜生成用コーティング液に用いられるイオン性液体は、常温（例えば、２０℃～４０℃）でも結晶化しない有機塩を含む液体である。イオン性液体は、代表的には、イミダゾールやトリアゾール等の窒素を含む環状化合物の陽イオンと、六フッ化リンやスルホン酸イミド等の陰イオンとの塩である。かかるイオン性液体は、１－ブチル－３－メチルイミダゾリウム塩、１－エチル－３－メチルイミダゾリウム塩又はこれらの混合物が、親水性溶媒への溶解性に優れるため好ましい。これらのイオン性液体は、例えば、日本合成化学社や、ＡＬＤＲＩＣＨ社から入手可能である。 [Ionic liquid]
The ionic liquid used in the coating liquid for producing a polarizing film of this embodiment is a liquid containing an organic salt that does not crystallize even at room temperature (for example, 20 ° C. to 40 ° C.). The ionic liquid is typically a salt of a cation of a cyclic compound containing nitrogen such as imidazole or triazole and an anion such as phosphorus hexafluoride or sulfonic imide. As such an ionic liquid, 1-butyl-3-methylimidazolium salt, 1-ethyl-3-methylimidazolium salt, or a mixture thereof is preferable because of its excellent solubility in a hydrophilic solvent. These ionic liquids are available from, for example, Nippon Synthetic Chemical Company or ALDRICH.
本実施形態の偏光膜生成用コーティング液に用いられるイオン性液体は、常温（例えば、２０℃～４０℃）でも結晶化しない有機塩を含む液体である。イオン性液体は、代表的には、イミダゾールやトリアゾール等の窒素を含む環状化合物の陽イオンと、六フッ化リンやスルホン酸イミド等の陰イオンとの塩である。かかるイオン性液体は、１－ブチル－３－メチルイミダゾリウム塩、１－エチル－３－メチルイミダゾリウム塩又はこれらの混合物が、親水性溶媒への溶解性に優れるため好ましい。これらのイオン性液体は、例えば、日本合成化学社や、ＡＬＤＲＩＣＨ社から入手可能である。 [Ionic liquid]
The ionic liquid used in the coating liquid for producing a polarizing film of this embodiment is a liquid containing an organic salt that does not crystallize even at room temperature (for example, 20 ° C. to 40 ° C.). The ionic liquid is typically a salt of a cation of a cyclic compound containing nitrogen such as imidazole or triazole and an anion such as phosphorus hexafluoride or sulfonic imide. As such an ionic liquid, 1-butyl-3-methylimidazolium salt, 1-ethyl-3-methylimidazolium salt, or a mixture thereof is preferable because of its excellent solubility in a hydrophilic solvent. These ionic liquids are available from, for example, Nippon Synthetic Chemical Company or ALDRICH.
イオン性液体の偏光膜生成用コーティング液への混合量は、全固形分１００重量部に対して、好ましくは１重量部～１５重量部である。イオン性液体の混合量が１重量部未満である場合は、乾燥過程で偏光度の低下を抑える効果が小さくなる虞があり、１５重量部を超える場合は、却ってアゾ化合物の配向が乱れ、偏光度が低下する虞がある。
The mixing amount of the ionic liquid to the polarizing film forming coating liquid is preferably 1 to 15 parts by weight with respect to 100 parts by weight of the total solid content. If the mixing amount of the ionic liquid is less than 1 part by weight, the effect of suppressing the decrease in the degree of polarization may be reduced during the drying process. If it exceeds 15 parts by weight, the orientation of the azo compound is disturbed, and the polarization There is a risk that the degree will decrease.
[アゾ化合物］
本実施形態の偏光膜生成用コーティング液に用いられるアゾ化合物は、陰イオン性基を有するものである。陰イオン性基としては、－ＳＯ3Ｍ、－ＣＯＯＭ、－ＰＯ3ＭＨ、－ＰＯ3Ｍ2などが挙げられる。ここに、Ｍは、水素原子、アルカリ金属、又はアンモニウム化合物である。 [Azo compounds]
The azo compound used in the coating liquid for producing a polarizing film of this embodiment has an anionic group. Examples of the anionic group include —SO 3 M, —COOM, —PO 3 MH, —PO 3 M 2 and the like. Here, M is a hydrogen atom, an alkali metal, or an ammonium compound.
本実施形態の偏光膜生成用コーティング液に用いられるアゾ化合物は、陰イオン性基を有するものである。陰イオン性基としては、－ＳＯ3Ｍ、－ＣＯＯＭ、－ＰＯ3ＭＨ、－ＰＯ3Ｍ2などが挙げられる。ここに、Ｍは、水素原子、アルカリ金属、又はアンモニウム化合物である。 [Azo compounds]
The azo compound used in the coating liquid for producing a polarizing film of this embodiment has an anionic group. Examples of the anionic group include —SO 3 M, —COOM, —PO 3 MH, —PO 3 M 2 and the like. Here, M is a hydrogen atom, an alkali metal, or an ammonium compound.
上記アゾ化合物は、好ましくは下記化１で表される化合物である。
このような化合物は、良好な配向性を示し、可視光領域（波長３８０ｎｍ～７８０ｎｍ）で吸収二色性を示す。
式中、Ｍは上記と同様、水素原子、アルカリ金属、又はアンモニウム化合物であり、Ｒは水素原子、炭素数１～３のアルキル基、アセチル基、ベンゾイル基、フェニル基、又はそれらの誘導体基を表す。Ｘは水素原子、ハロゲン原子、ニトロ基、シアノ基、炭素数１～４のアルキル基、炭素数１～４のアルコキシ基、又は－ＳＯ3Ｍ基を表す。
上記アゾ化合物は、例えば、アニリン誘導体とナフタレン誘導体とを常法によりジアゾ化およびカップリング反応させてモノアゾ化合物とした後、更にジアゾ化し、１－アミノ－８－ナフトール誘導体とカップリング反応させて得ることができる。 The azo compound is preferably a compound represented by the followingchemical formula 1.
Such a compound exhibits good orientation and exhibits absorption dichroism in the visible light region (wavelength 380 nm to 780 nm).
In the formula, M is a hydrogen atom, an alkali metal, or an ammonium compound as described above, and R is a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, an acetyl group, a benzoyl group, a phenyl group, or a derivative group thereof. To express. X represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or an —SO 3 M group.
The azo compound can be obtained, for example, by subjecting an aniline derivative and a naphthalene derivative to diazotization and coupling reaction by a conventional method to obtain a monoazo compound, followed by further diazotization and coupling reaction with a 1-amino-8-naphthol derivative. be able to.
このような化合物は、良好な配向性を示し、可視光領域（波長３８０ｎｍ～７８０ｎｍ）で吸収二色性を示す。
上記アゾ化合物は、例えば、アニリン誘導体とナフタレン誘導体とを常法によりジアゾ化およびカップリング反応させてモノアゾ化合物とした後、更にジアゾ化し、１－アミノ－８－ナフトール誘導体とカップリング反応させて得ることができる。 The azo compound is preferably a compound represented by the following
Such a compound exhibits good orientation and exhibits absorption dichroism in the visible light region (wavelength 380 nm to 780 nm).
The azo compound can be obtained, for example, by subjecting an aniline derivative and a naphthalene derivative to diazotization and coupling reaction by a conventional method to obtain a monoazo compound, followed by further diazotization and coupling reaction with a 1-amino-8-naphthol derivative. be able to.
[溶媒］
本実施形態の偏光膜生成用コーティング液に用いられる溶媒は、アゾ化合物を溶解するものであり、好ましくは親水性溶媒が用いられる。親水性溶媒は、好ましくは水、アルコール類、セロソルブ類及びそれらの混合溶媒である。 [solvent]
The solvent used in the coating liquid for forming a polarizing film of this embodiment is one that dissolves an azo compound, and preferably a hydrophilic solvent is used. The hydrophilic solvent is preferably water, alcohols, cellosolves or a mixed solvent thereof.
本実施形態の偏光膜生成用コーティング液に用いられる溶媒は、アゾ化合物を溶解するものであり、好ましくは親水性溶媒が用いられる。親水性溶媒は、好ましくは水、アルコール類、セロソルブ類及びそれらの混合溶媒である。 [solvent]
The solvent used in the coating liquid for forming a polarizing film of this embodiment is one that dissolves an azo compound, and preferably a hydrophilic solvent is used. The hydrophilic solvent is preferably water, alcohols, cellosolves or a mixed solvent thereof.
［偏光膜］
本実施形態に係る偏光膜は、上記コーティング液を簿膜状に流廷し溶媒を蒸発させて得られるものである。上記偏光膜の厚みは、好ましくは０．１μｍ以上１０μｍ未満である。流廷手段はコーティング液を均－に流延できるものであれば特に制限はなく、適切なコータ、例えばスライドコータ、スロットダイコータ、バーコータ等が用いられる。転燥方法は、例えば、自然乾燥、減圧乾燥、加熱乾燥などが用いられる。乾燥温度は、好ましくは５０℃～１２０℃である。 [Polarizing film]
The polarizing film according to this embodiment is obtained by flowing the coating liquid into a book film and evaporating the solvent. The thickness of the polarizing film is preferably 0.1 μm or more and less than 10 μm. The court means is not particularly limited as long as the coating liquid can be uniformly cast, and an appropriate coater such as a slide coater, a slot die coater, a bar coater, or the like is used. As the drying method, for example, natural drying, reduced pressure drying, heat drying or the like is used. The drying temperature is preferably 50 ° C to 120 ° C.
本実施形態に係る偏光膜は、上記コーティング液を簿膜状に流廷し溶媒を蒸発させて得られるものである。上記偏光膜の厚みは、好ましくは０．１μｍ以上１０μｍ未満である。流廷手段はコーティング液を均－に流延できるものであれば特に制限はなく、適切なコータ、例えばスライドコータ、スロットダイコータ、バーコータ等が用いられる。転燥方法は、例えば、自然乾燥、減圧乾燥、加熱乾燥などが用いられる。乾燥温度は、好ましくは５０℃～１２０℃である。 [Polarizing film]
The polarizing film according to this embodiment is obtained by flowing the coating liquid into a book film and evaporating the solvent. The thickness of the polarizing film is preferably 0.1 μm or more and less than 10 μm. The court means is not particularly limited as long as the coating liquid can be uniformly cast, and an appropriate coater such as a slide coater, a slot die coater, a bar coater, or the like is used. As the drying method, for example, natural drying, reduced pressure drying, heat drying or the like is used. The drying temperature is preferably 50 ° C to 120 ° C.
下記化２で表されるアゾ化合物と、イオン性液体（日本合成化学社製 １－ブチル－３－メチルイミダゾリウムテトラフルオロボラート）とを水に溶解して、液晶性を示す偏光膜生成用コーティング液を調製した。
For producing a polarizing film exhibiting liquid crystallinity by dissolving an azo compound represented by Chemical Formula 2 below and an ionic liquid (manufactured by Nippon Synthetic Chemical Co., Ltd., 1-butyl-3-methylimidazolium tetrafluoroborate) in water. A coating solution was prepared.
この偏光膜生成用コーティング液を、厚み１００μｍのシクロオレフィン系樹脂フィルム（日本ゼオン社製 商品名「ＺＥＯＮＯＲ」）上にバーコータ（ＢＵＳＨＭＡＮ社製）を用いて薄膜状に流延し、水分を蒸発させて、シクロオレフィン系樹脂フィルム上に、厚み０．２μｍの偏光膜を作製した。コーティング液から水分が蒸発し、偏光膜が生成されるまでの乾燥過程における偏光度変化（グラフ）を図２に示す。
This polarizing film-generating coating solution is cast into a thin film using a bar coater (manufactured by BUSHMAN) on a cycloolefin resin film (manufactured by Nippon Zeon Co., Ltd., trade name “ZEONOR”) to evaporate moisture. Then, a polarizing film having a thickness of 0.2 μm was produced on the cycloolefin-based resin film. FIG. 2 shows a change in polarization degree (graph) in the drying process until moisture is evaporated from the coating liquid and a polarizing film is formed.
イオン性液体として、１－エチル－３－メチルピリジニウムエチルスルファート（東京化成工業株式会社製）を用いた以外は、実施例１と同様に、偏光膜生成用コーティング液を調製し、偏光膜を作製した。かかる偏光膜生成用コーティング液から水分が蒸発し、偏光膜が生成されるまでの乾燥過程における偏光度変化を測定したところ、実施例１の場合と同様、図２に示すグラフが得られた。
A polarizing film producing coating solution was prepared in the same manner as in Example 1 except that 1-ethyl-3-methylpyridinium ethyl sulfate (manufactured by Tokyo Chemical Industry Co., Ltd.) was used as the ionic liquid. Produced. When the change in the degree of polarization in the drying process until moisture was evaporated from the coating liquid for forming a polarizing film and the polarizing film was formed was measured, the graph shown in FIG. 2 was obtained as in the case of Example 1.
イオン性液体を混合しなかった以外は、実施例１と同様の方法で偏光膜生成用コーティング液を調製し、その偏光膜生成用コーティング液を用いて偏光膜を作製した。偏光膜生成用コーティング液から水分が蒸発し、備光膜が生成されるまでの乾燥過程における偏光度変化（グラフ）を、図３に示す。
A polarizing film producing coating solution was prepared in the same manner as in Example 1 except that the ionic liquid was not mixed, and a polarizing film was produced using the polarizing film producing coating solution. FIG. 3 shows a change in polarization degree (graph) in the drying process until moisture is evaporated from the polarizing film-generating coating liquid and a light-repelling film is generated.
［評価］
図２及び図３において、横軸は乾燥時間（ｓｅｃ）、縦軸は偏光度を表し、実施例１及び実施例２の偏光膜生成用コーティング液の場合、図２に示すように、偏光膜の偏光度は、乾燥時間が８０秒付近になった時点で最高となり、それ以後も高い偏光度（９８．３％）がそのまま維持された。一方、比較例に係る偏光膜生成用コーティング液の場合、図３に示すように、偏光膜の偏光度は乾燥時間８０秒付近で最高値（９８％）を示した後、それ以後において偏光度は１％程度低下した。 [Evaluation]
2 and 3, the horizontal axis represents the drying time (sec), and the vertical axis represents the degree of polarization. In the case of the coating liquid for producing a polarizing film of Example 1 and Example 2, as shown in FIG. The degree of polarization was the highest when the drying time was around 80 seconds, and the high degree of polarization (98.3%) was maintained as it was thereafter. On the other hand, in the case of the coating liquid for producing a polarizing film according to the comparative example, as shown in FIG. 3, the degree of polarization of the polarizing film shows a maximum value (98%) at a drying time of about 80 seconds, and thereafter the degree of polarization is increased. Decreased by about 1%.
図２及び図３において、横軸は乾燥時間（ｓｅｃ）、縦軸は偏光度を表し、実施例１及び実施例２の偏光膜生成用コーティング液の場合、図２に示すように、偏光膜の偏光度は、乾燥時間が８０秒付近になった時点で最高となり、それ以後も高い偏光度（９８．３％）がそのまま維持された。一方、比較例に係る偏光膜生成用コーティング液の場合、図３に示すように、偏光膜の偏光度は乾燥時間８０秒付近で最高値（９８％）を示した後、それ以後において偏光度は１％程度低下した。 [Evaluation]
2 and 3, the horizontal axis represents the drying time (sec), and the vertical axis represents the degree of polarization. In the case of the coating liquid for producing a polarizing film of Example 1 and Example 2, as shown in FIG. The degree of polarization was the highest when the drying time was around 80 seconds, and the high degree of polarization (98.3%) was maintained as it was thereafter. On the other hand, in the case of the coating liquid for producing a polarizing film according to the comparative example, as shown in FIG. 3, the degree of polarization of the polarizing film shows a maximum value (98%) at a drying time of about 80 seconds, and thereafter the degree of polarization is increased. Decreased by about 1%.
［実施例、比較例で用いた測定方法］
［偏光膜の厚みの測定方法］
偏光膜の一部を剥離し、触針式表面形状測定器（Ｖｅｅｃｏ社製 製品名「Ｄｅｋｔａｋ」を用いて求めた。
［偏光度の測定方法］
ポラリメーター（ＡＸＯＭＥＴＲＩＣＳ社製 製品名「ＡｘｏＳｃａｎ」）を用いて、偏光膜を２３℃の室温で自然乾燥させながら、偏光度を測定した。 [Measurement methods used in Examples and Comparative Examples]
[Measurement method of polarizing film thickness]
A part of the polarizing film was peeled off and obtained using a stylus type surface shape measuring instrument (product name “Dektak” manufactured by Veeco).
[Measurement method of polarization degree]
Using a polarimeter (product name “AxoScan” manufactured by AXOMETRICS), the degree of polarization was measured while naturally drying the polarizing film at a room temperature of 23 ° C.
［偏光膜の厚みの測定方法］
偏光膜の一部を剥離し、触針式表面形状測定器（Ｖｅｅｃｏ社製 製品名「Ｄｅｋｔａｋ」を用いて求めた。
［偏光度の測定方法］
ポラリメーター（ＡＸＯＭＥＴＲＩＣＳ社製 製品名「ＡｘｏＳｃａｎ」）を用いて、偏光膜を２３℃の室温で自然乾燥させながら、偏光度を測定した。 [Measurement methods used in Examples and Comparative Examples]
[Measurement method of polarizing film thickness]
A part of the polarizing film was peeled off and obtained using a stylus type surface shape measuring instrument (product name “Dektak” manufactured by Veeco).
[Measurement method of polarization degree]
Using a polarimeter (product name “AxoScan” manufactured by AXOMETRICS), the degree of polarization was measured while naturally drying the polarizing film at a room temperature of 23 ° C.
本発明は、薄膜状に流延して溶媒を蒸発させて偏光膜を生成する際に、溶媒の蒸発に従って乾燥していく場合においても、偏光度の低下を抑制して高い偏光度を有する偏光膜を生成可能な偏光膜生成用コーティング液及びその偏光膜生成用コーティング液から生成される偏光膜を提供でき、産業上奏する効果は大きい。
In the case of producing a polarizing film by casting a thin film and evaporating the solvent, the present invention suppresses a decrease in the degree of polarization and has a high degree of polarization even when drying according to the evaporation of the solvent. A polarizing film generating coating liquid capable of generating a film and a polarizing film generated from the polarizing film generating coating liquid can be provided, and the effect exerted industrially is great.
Claims (6)
- 陰イオン性基を有するアゾ化合物と、
前記アゾ化合物を溶解する溶媒と、
イオン性液体とを含有することを特徴とする偏光膜生成用コーティング液。 An azo compound having an anionic group;
A solvent for dissolving the azo compound;
A coating liquid for producing a polarizing film, comprising an ionic liquid. - 請求項１に記載の偏光膜生成用コーティング液を薄膜状に流延し溶媒を蒸発させて得られる偏光膜。 A polarizing film obtained by casting the coating liquid for forming a polarizing film according to claim 1 into a thin film and evaporating the solvent.
- 前記アゾ化合物は、０．５重量％～５０重量％の範囲で前記偏光膜生成用コーティング液に含有されていることを特徴とする請求項１に記載の偏光膜生成用コーティング液。 2. The polarizing film generating coating liquid according to claim 1, wherein the azo compound is contained in the polarizing film generating coating liquid in a range of 0.5 wt% to 50 wt%.
- 前記アゾ化合物は、下記化１で表わされる化合物であることを特徴とする請求項１又は請求項３に記載の偏光膜生成用コーティング液。
- 前記イオン性液体は、全固形分１００重量部に対して１重量部～１５重量部の範囲で含有されていることを特徴とする請求項１、請求項３又は請求項４に記載の偏光膜生成用コーティング液。 5. The polarizing film according to claim 1, wherein the ionic liquid is contained in an amount of 1 to 15 parts by weight with respect to 100 parts by weight of the total solid content. Coating liquid for generation.
- 前記イオン性液体は、１－ブチル－３－メチルイミダゾリウム塩、１－エチル－３－メチルイミダゾリウム塩又はこれらの混合物から選択されることを特徴とする請求項１、請求項３、請求項４又は請求項５に記載の偏光膜生成用コーティング液。 The ionic liquid is selected from 1-butyl-3-methylimidazolium salt, 1-ethyl-3-methylimidazolium salt, or a mixture thereof. The polarizing film production | generation coating liquid of Claim 4 or Claim 5.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2009-276780 | 2009-12-04 | ||
| JP2009276780A JP2011118237A (en) | 2009-12-04 | 2009-12-04 | Coating liquid for forming polarizing film, and polarizing film |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2011067959A1 true WO2011067959A1 (en) | 2011-06-09 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/JP2010/061008 WO2011067959A1 (en) | 2009-12-04 | 2010-06-29 | Coating liquid for forming polarizing film, and polarizing film |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JP2011118237A (en) |
| TW (1) | TW201120164A (en) |
| WO (1) | WO2011067959A1 (en) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JP7127834B2 (en) * | 2017-02-20 | 2022-08-30 | 公立大学法人大阪 | Compositions containing liquid dyes, membranes, methods of making the same, chemical sensors, liquid dyes, methods of making liquid dyes, devices or kits for simple testing (drug discovery and/or diagnostic analysis), and thin film luminescent materials |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0289008A (en) * | 1988-09-26 | 1990-03-29 | Sumitomo Chem Co Ltd | Production of polarizing film and polarizing plate of dye system |
| JP2001517329A (en) * | 1997-12-16 | 2001-10-02 | ゴスダルストベンニ ナウチニ ツェントル ロシイスコイ フェデラツィイ“ニオピク”（ゲーエヌテーエス エルエフ“ニオピク”） | Polarizer and liquid crystal display device |
| JP2005128152A (en) * | 2003-10-22 | 2005-05-19 | Fuji Photo Film Co Ltd | Composition and nonlinear optical material |
| JP2007241036A (en) * | 2006-03-10 | 2007-09-20 | Toppan Printing Co Ltd | Anisotropic scattering element and its manufacturing method |
| JP2009173849A (en) * | 2007-12-28 | 2009-08-06 | Nitto Denko Corp | Liquid-crystalline coating liquid, and polarizing film |
-
2009
- 2009-12-04 JP JP2009276780A patent/JP2011118237A/en active Pending
-
2010
- 2010-06-29 WO PCT/JP2010/061008 patent/WO2011067959A1/en active Application Filing
- 2010-07-13 TW TW099122963A patent/TW201120164A/en unknown
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0289008A (en) * | 1988-09-26 | 1990-03-29 | Sumitomo Chem Co Ltd | Production of polarizing film and polarizing plate of dye system |
| JP2001517329A (en) * | 1997-12-16 | 2001-10-02 | ゴスダルストベンニ ナウチニ ツェントル ロシイスコイ フェデラツィイ“ニオピク”（ゲーエヌテーエス エルエフ“ニオピク”） | Polarizer and liquid crystal display device |
| JP2005128152A (en) * | 2003-10-22 | 2005-05-19 | Fuji Photo Film Co Ltd | Composition and nonlinear optical material |
| JP2007241036A (en) * | 2006-03-10 | 2007-09-20 | Toppan Printing Co Ltd | Anisotropic scattering element and its manufacturing method |
| JP2009173849A (en) * | 2007-12-28 | 2009-08-06 | Nitto Denko Corp | Liquid-crystalline coating liquid, and polarizing film |
Also Published As
| Publication number | Publication date |
|---|---|
| TW201120164A (en) | 2011-06-16 |
| JP2011118237A (en) | 2011-06-16 |
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