JPH01265205A - Polarizing plate - Google Patents
Polarizing plateInfo
- Publication number
- JPH01265205A JPH01265205A JP9337988A JP9337988A JPH01265205A JP H01265205 A JPH01265205 A JP H01265205A JP 9337988 A JP9337988 A JP 9337988A JP 9337988 A JP9337988 A JP 9337988A JP H01265205 A JPH01265205 A JP H01265205A
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- sulfonic acid
- polarizing plate
- hydrogen atom
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 125000000542 sulfonic acid group Chemical group 0.000 claims abstract description 24
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 14
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 125000003277 amino group Chemical group 0.000 claims abstract description 7
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 43
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims 3
- 238000000576 coating method Methods 0.000 abstract description 10
- 239000011248 coating agent Substances 0.000 abstract description 7
- 238000002156 mixing Methods 0.000 abstract description 3
- 230000010287 polarization Effects 0.000 description 19
- 239000000975 dye Substances 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 238000000034 method Methods 0.000 description 10
- 238000002834 transmittance Methods 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 7
- 238000007796 conventional method Methods 0.000 description 6
- 239000011521 glass Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 230000008878 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000002736 nonionic surfactant Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- -1 polypropylene Polymers 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- 229920002284 Cellulose triacetate Polymers 0.000 description 2
- 239000004695 Polyether sulfone Substances 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000004957 naphthylene group Chemical group 0.000 description 2
- 239000000123 paper Substances 0.000 description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
- 229920006267 polyester film Polymers 0.000 description 2
- 229920006393 polyether sulfone Polymers 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 241000270666 Testudines Species 0.000 description 1
- 239000003082 abrasive agent Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 238000003851 corona treatment Methods 0.000 description 1
- 229920005994 diacetyl cellulose Polymers 0.000 description 1
- 150000002169 ethanolamines Chemical class 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
Landscapes
- Polarising Elements (AREA)
Abstract
Description
【発明の詳細な説明】
産業上の利用分野
本発明は染料で塗布されてなる偏光板に関し更に詳しく
は任意の方向に偏光性を与え、かつその偏光部分が連続
的にパターン化された偏光板に関する。DETAILED DESCRIPTION OF THE INVENTION Field of Industrial Application The present invention relates to a polarizing plate coated with a dye, and more specifically to a polarizing plate which provides polarization in any direction and whose polarizing portion is continuously patterned. Regarding.
従来の技術
従来、偏光板を製造する代表的な方法としては、延伸ポ
リビニルアルコール膜をヨウ素で着色したのち透明基板
に貼着する方法がある。この種の偏光板は高い偏光度、
透過率の均一性、材質の安定性において優れている。し
かし、この偏光板は、ポリビニルアルコール膜の延伸方
向にのみ偏光性が得られるものであり、この延伸が通常
一方向にしか出来ないため、偏光方向も一方向に限定さ
れ、円状、放射状、波状等の偏光板を製造することが出
来ないという欠点がある。BACKGROUND OF THE INVENTION Conventionally, a typical method for manufacturing a polarizing plate includes a method in which a stretched polyvinyl alcohol film is colored with iodine and then attached to a transparent substrate. This kind of polarizing plate has a high degree of polarization,
Excellent in transmittance uniformity and material stability. However, this polarizing plate can obtain polarization only in the stretching direction of the polyvinyl alcohol film, and since this stretching can usually only be done in one direction, the polarizing direction is also limited to one direction, such as circular, radial, There is a drawback that it is not possible to manufacture a polarizing plate having a wave shape or the like.
従って、この種の偏光板を用いて例えば偏光軸が放射状
に伸びた偏光板を得るには、扇状形に切断された、半径
方向に偏光性を有する多数の偏光板を円状に貼着する等
の方法を採用しなければならないため、製作も困難であ
り、高価なものとなり、且つ連続的な偏光軸をもった偏
光板が得られにくいという欠点がある。Therefore, in order to obtain a polarizing plate in which the polarization axis extends radially using this type of polarizing plate, for example, a large number of polarizing plates cut into fan shapes and having polarizing properties in the radial direction are pasted in a circular shape. This method is difficult and expensive to manufacture, and it is difficult to obtain a polarizing plate with a continuous polarization axis.
一方、ガラス、有機膜等に偏光性を直接形成させろ方法
としては、例えば米国特許第２．４００，８７７号等に
記載されている方法がある。On the other hand, as a method for directly forming polarizing properties on glass, organic films, etc., there is a method described, for example, in US Pat. No. 2,400,877.
この方法は、ガラス、或いは有機膜を予め、布、紙、パ
フ等でラビングしておき、その後、二色性色素をコーテ
ィングしてラビングされた方向に二色性色素を配向させ
る方法である。この方法は、二色性色素をコーティング
する前に、ガラス、或いは有機膜にラビング処理を行い
、このラビング方向に二色性色素を配向させるもの・で
あり、ラビング方向を任意に変えることにより、連続的
にパターン化された、むらの少ない偏光板を形成するこ
とが出来る。しかし、該米国！持許記載の二色性色素を
用い、ガラス、或いは有機膜に偏光性を直接形成させた
場合、偏光能が低く、コントラストが優れな（・と−・
う欠点がある。In this method, glass or an organic film is rubbed in advance with cloth, paper, puff, etc., and then a dichroic dye is coated and the dichroic dye is oriented in the direction of the rubbing. In this method, before coating the dichroic dye, the glass or organic film is rubbed, and the dichroic dye is oriented in the rubbing direction. By arbitrarily changing the rubbing direction, A continuously patterned polarizing plate with less unevenness can be formed. But the US! When polarizing properties are directly formed on glass or organic films using the dichroic dye described in the patent, the polarizing ability is low and the contrast is excellent (...
There are some drawbacks.
発明が解決しようとする課題
偏光能が高く、コントラストに優れ、任意の方向に偏光
性を与え、偏光部分が連続的にパターン化された、むら
の少ない偏光板が望まれている。Problems to be Solved by the Invention There is a need for a polarizing plate with high polarization ability, excellent contrast, polarization in any direction, continuous pattern of polarization portions, and less unevenness.
課題を解決するための手段
染料を用いた偏光板において、偏光軸が任意の方向であ
って、偏光能力が高く、コントラストの優れた偏光板を
得るべく鋭意研発を重ねた結果本発明に至った。Means for Solving the Problems In order to obtain a polarizing plate using a dye, the polarization axis can be set in any direction, the polarization ability is high, and the contrast is excellent.As a result of intensive research, the present invention has been achieved. Ta.
即ち、本発明は式（１）
〔式（１１において、ＡＩは低級アルキル基、低級アル
コキシ基又はスルホン酸基で置換されてし・てもよいフ
ェニル基を、 Ａ２はスルホン酸基で置換されていても
よいフェニル基を、Ｒ３とＲ４は水素原子、水酸基又は
低級アルコキシ基を、Ｒ２＊ １１３１Ｒｓ、１１ａは
それぞれ独立に水素原子、水酸基又はスルホン酸基を、
Ｒ７は水素原子、メチル基又は置換されていてもよいフ
ェニル基をそれぞれ表す。〕
で表される化合物と下記式（ＩＩ）及び／′又は（Ｉｎ
）〔式（１１）において、Ｒ，、ＩＩ、は互いに独立し
て水素原子、メチル基、メトキシ基又はスルホン酸基を
、Ｂは水酸基、スルホン酸基又はアミノ基で置換された
ナフチル基をそれぞれ表す。〕〔式（ＩＩ）において、
Ｃは水酸基、アミノ基又はスルホン酸基で置換さ扛てい
てもよいナフチル基を、Ｄは低級アルキル基、低級アル
コキシ基、水酸基若しくはスルホン酸基で置換されそい
てもよいフェニレン基又はナフチレン基を、Ｒ＋ｏハ水
素原子、メチル基、アセチル基、カルバモイル基、置換
されていてもよいフェニル基又はベンゾイル基をそれぞ
れ表す。〕で表される化合物との混合物を塗布してなる
偏光板を提供する。That is, the present invention provides formula (1) [In formula (11, AI is a phenyl group optionally substituted with a lower alkyl group, a lower alkoxy group, or a sulfonic acid group, and A2 is a phenyl group substituted with a sulfonic acid group) R3 and R4 are hydrogen atoms, hydroxyl groups or lower alkoxy groups, R2* 1131Rs and 11a are each independently hydrogen atoms, hydroxyl groups or sulfonic acid groups,
R7 represents a hydrogen atom, a methyl group, or an optionally substituted phenyl group, respectively. ] A compound represented by the following formula (II) and /' or (In
) [In formula (11), R, II independently represent a hydrogen atom, a methyl group, a methoxy group, or a sulfonic acid group, and B represents a naphthyl group substituted with a hydroxyl group, a sulfonic acid group, or an amino group, respectively. represent. ] [In formula (II),
C is a naphthyl group which may be substituted with a hydroxyl group, an amino group or a sulfonic acid group, and D is a phenylene group or a naphthylene group which may be substituted with a lower alkyl group, a lower alkoxy group, a hydroxyl group or a sulfonic acid group. , R+o each represent a hydrogen atom, a methyl group, an acetyl group, a carbamoyl group, an optionally substituted phenyl group or a benzoyl group. ] A polarizing plate is provided which is coated with a mixture of the compound represented by:
本発明で用いる式（１）で表される化合物は、−膜内に
は次の方法によって製造出来る。即ち、式ＧＶ）
ＡＩ Ｎｌ２ ＧＶ）
〔式（ＩＶ）において、 ＡＩは低級アルキル基、低級
アルコキシ基又はスルボン酸基で置換されていてもよい
フェニル基を表す。〕で表される化合物を常法によりジ
アゾ化し、弐Ｍ
Ｒ１
〔式（■において、ＲＩは水素原子、水酸基又は低級ア
ルコキシ基を、 Ｒ２とＲ３はそれぞれ独立に水素原子
、水酸基又はスルホン酸基を表す。〕で表される化合物
にカップリングし、式（７）〔式（■中、ＡＩ、ＲＩ、
Ｒ２及び亀は前記と同じ意味を表す。〕で表される化合
物を製造する。更に式例の化合物を常法によりジアゾ化
して式（■１）ｐ。The compound represented by formula (1) used in the present invention can be produced in the membrane by the following method. That is, formula GV) AI Nl2 GV) [In formula (IV), AI represents a phenyl group which may be substituted with a lower alkyl group, a lower alkoxy group, or a sulfonic acid group. ] A compound represented by the formula is diazotized by a conventional method, and 2 M is coupled to a compound represented by the formula (7) [formula (■, AI, RI,
R2 and turtle have the same meanings as above. ] is produced. Further, the compound of the formula example is diazotized by a conventional method to obtain the formula (■1)p.
〔式（ｖＩＩ）において、Ｒ４は水素原子、水酸基又は
低級アルコキシ基を、Ｒ５と凡はそれぞれ独立に水素原
子、水酸基又はスルホン酸基を表す。〕で表される化合
物にカップリングし、式（Ｖｌｌｌ）〔式（Ｖｌｌｌ）
中、ん、 Ｒ１，Ｒ２，Ｒ３，Ｒ４，Ｒ５及び＆は前記
と同じ意味を表す。〕で表される化合物を製造する。[In formula (vII), R4 represents a hydrogen atom, a hydroxyl group, or a lower alkoxy group, and R5 and R5 each independently represent a hydrogen atom, a hydroxyl group, or a sulfonic acid group. ] to a compound represented by the formula (Vllll) [formula (Vllll)
Naka, N, R1, R2, R3, R4, R5 and & represent the same meanings as above. ] is produced.
次いで、別途に、式（ＩＸ）
ん−Ｎｌ２（ＩＸ）
〔式（ＩＸ）中、Ａ２はスルホン酸基で置換されていて
もよいフェニル基を表す。〕で表される化合物を常法に
よりジアゾ化し、式（Ｘ）〔式（１）において、Ｒ７は
水素原子、メチル基又は置換されていてもよいフェニル
基を表ｔ。〕で表される化合物と酸性下でカップリング
し、式（ＸＩ）
Ｎ＝Ｎ Ａ２
〔式（ＸＩ）中、ん及びＲ７は前記と同じ意味を表す。Then, separately, formula (IX) -Nl2(IX) [In formula (IX), A2 represents a phenyl group which may be substituted with a sulfonic acid group. ] A compound represented by the formula (X) is diazotized by a conventional method, and R7 is a hydrogen atom, a methyl group, or an optionally substituted phenyl group. [In formula (XI), N and R7 represent the same meanings as above.
〕で表される化合物を得る。次いで、式（Ｖメで表さ扛
る化合物を常法によりジアゾ化し、ピリジン水溶液中で
式（ＸＩ）で表される化合物とカップリングすることに
よって製造する。もちろん、これり外の製造ルートによ
っても式（１）で表される化合物を製造することが出来
る。] is obtained. Next, the compound represented by the formula (V) is diazotized by a conventional method, and the compound is produced by coupling with the compound represented by the formula (XI) in an aqueous pyridine solution.Of course, it can be produced by other production routes. It is also possible to produce a compound represented by formula (1).
式（ＩＶ）で表される化合物の具体例としては、等を挙
げることが出来る。（式中「Ｓ」はｒＳＯＪ−ｊＪを意
味する。以下同じ。）
弐Ｍ及び（Ｖｌ）で表される化合物の具体例とじては。Specific examples of the compound represented by formula (IV) include the following. (In the formula, "S" means rSOJ-jJ. The same applies hereinafter.) Specific examples of the compounds represented by 2M and (Vl) are as follows.
ＯＨ 等を挙げることが出来る。OH etc. can be mentioned.
式（Ｘ）で表される化合物の具体例としては、０、■１ 等を挙げることが出来る。Specific examples of the compound represented by formula (X) include 0, ■1 etc. can be mentioned.
文武（ＩＸ）で表される化合物の具体例としては等を挙
げることが出来る。Specific examples of the compound represented by Bunmu (IX) include the following.
本発明で用いる式（ロ）で表される化合物は、−膜内に
は次の方法によって製造出来る。即ち、式（ＸＩＩ）
Ｂ−ＮＨ２（ＸＩＩ）
〔式（Ｘｌｌ ）において、Ｂは水酸基、スルホン酸基
、又はアミノ基で置換さ扛たナフチル基を表す。〕で表
される化合物を常法によりジアゾ化し、式（■）
〔式（■）において、Ｒ８，Ｒ９は互いに独立して水素
原子。メチル基、メトキシ基又はスルホン酸基を表す。The compound represented by formula (b) used in the present invention can be produced in the membrane by the following method. That is, Formula (XII) B-NH2(XII) [In Formula (Xll), B represents a naphthyl group substituted with a hydroxyl group, a sulfonic acid group, or an amino group. ] A compound represented by the formula (■) is diazotized by a conventional method to obtain the formula (■) [In the formula (■), R8 and R9 are independently hydrogen atoms. Represents a methyl group, a methoxy group, or a sulfonic acid group.
〕で表される化合物とカップリングすることによって得
らｎた化合物２モルを、塩基の存在下で、ホスゲン１モ
ルと縮合することによって製造する。もちろん、これ以
外の製造ルートによっても弐（ＩＩ）で表される化合物
を製造することが出来る。It is produced by condensing 2 moles of the compound obtained by coupling with the compound represented by ] with 1 mole of phosgene in the presence of a base. Of course, the compound represented by II (II) can also be produced by other production routes.
式（Ｘｌｌ）で表される化合物の具体例としては、等を
挙げることが出来る。Specific examples of the compound represented by formula (Xll) include the following.
式（■）で表さ扛る化合物の具体例としては、等を挙げ
ることが出来る。Specific examples of the compound represented by formula (■) include the following.
本発明で用いる式（１）で表される化合物は、−膜内に
は次の方法によって製造出来る。即ち、式（ＸＩＶ）
ｃ −Ｎｌｌ２（ＸＩＶ）
〔式（′ｙＪＶ）において、Ｃは水酸基、アミノ基又は
スルホン酸基で置換されていてもよいナフチル基を表す
。〕で表される化合物を常法によりジアゾ化し、式（Ｘ
Ｖ）
Ｄ −ＮＦ２（ＸＶ）
〔式（ＸＶ）において、Ｄは低級アルキル基、低級アル
コキシ基、水酸基若しくはスルホン酸基で置換されてい
てもよいフェニレン基又はナフチレン基を表す。〕で表
される化合物にカップリングし、式■）
Ｃ−Ｎ＝Ｎ−Ｄ−ＮＦ２ （ＸＶＩ）〔式（Ｘ
ＶＩ）中、Ｃ及びＤは前記と同じ意味を表す。〕で表さ
れる化合物を製造する。更に、式（ＸＶＩ）の化合物を
常法によりジアゾ化して式（ＸＶＩＩ）Ｈ
〔式（Ｘ１１１１）において、１１１Ｇは水素原子、メ
チル基、アセチル基、カルバモイル基、置換すれていて
もよいフェニル基又はベンゾイル基を表す。〕で表され
る化合物とカップリングすることによって製造する。も
ちろん、これ以外の製造ルートによっても式（ＩＩ）で
表される化合物を製造することが出来る。The compound represented by formula (1) used in the present invention can be produced in the membrane by the following method. That is, formula (XIV) c -Nll2(XIV) [In formula ('yJV), C represents a naphthyl group which may be substituted with a hydroxyl group, an amino group or a sulfonic acid group. ] The compound represented by the formula (X
V) D -NF2(XV) [In formula (XV), D represents a phenylene group or naphthylene group which may be substituted with a lower alkyl group, a lower alkoxy group, a hydroxyl group, or a sulfonic acid group. ], and the formula (■) C-N=N-D-NF2 (XVI) [formula (X
VI), C and D represent the same meanings as above. ] is produced. Furthermore, the compound of formula (XVI) is diazotized by a conventional method to obtain formula (XVII)H [In formula (X1111), 111G is a hydrogen atom, a methyl group, an acetyl group, a carbamoyl group, an optionally substituted phenyl group, or Represents a benzoyl group. It is produced by coupling with a compound represented by ]. Of course, the compound represented by formula (II) can also be produced by other production routes.
式（ｘｒｖ）で表される化合物の具体例としては、等を
挙げることが出来る。Specific examples of the compound represented by formula (xrv) include the following.
式（ＸＶ）で表される化合物の具体例としては、等を挙
げることが出来る。Specific examples of the compound represented by formula (XV) include the following.
式（ＸＶｌｌ）で表される化合物の具体例としては、等
を挙げることが出来る。Specific examples of the compound represented by formula (XVll) include the following.
式（１）、（Ｉｌｌ、（Ｉ［）で表される化合物は通常
す） ＩＪウム塩として利用するが、それらは遊離酸と
して、或いは、カリウム塩、リチウム塩、アンモニウム
塩、アルキルアミン類、エタノールアミン類の塩として
も利用することが出来る。Compounds represented by formula (1), (Ill, (I[)) are usually used as IJium salts, but they can also be used as free acids, potassium salts, lithium salts, ammonium salts, alkylamines, It can also be used as a salt of ethanolamines.
弐（１１、（■）、（ＩＩ）で表される化合物はそれぞ
れ単独で用いた場合においても偏光能を有するが、二種
又は三種を配合することにより、単独の場合よりも優れ
た偏光能を有する偏光板を製造出来る。更に、弐（１）
、 （ｆｌｌ、（ＩＩＩ）の配合比を変えることにより
種々の色相を有する偏光板を製造することが出来る。The compounds represented by 2 (11, (■), and (II) each have polarizing ability even when used alone, but by blending two or three types, they have polarizing ability that is superior to that when used alone. It is possible to manufacture a polarizing plate having
, (fll, (III)), polarizing plates having various hues can be manufactured.
本発明の偏光板は、−膜内には予めラビング処理を施し
た基材上に、式（１）で表される化合物と（Ｕ）及び／
′又はｆ、ＩＩ、ｌで表される化合物とを含有した溶液
を塗布することにより得られる。 “本発明の偏
光板に用いられる基材としては、ガラスの他、トリアセ
チルセルローズフィルム（以下ＴＡＣフィルムという）
、ジアセチルセルローズフィルム、セルローズアセテー
トフィルム、ポリエステルフィルム、塩化ビニールフィ
ルム、ポリスチレンフィルム、ポリプロピレンフィルム
、ポリアミドフィルム、ポリエチレンフィルム、ポリエ
ーテルスルホンフィルム、アク’Ｊ ル系フィルム等が
用いられるが、これらのうち好ましいものは、Ｔへ〇フ
ィルム、ポリエステルフィルム等を挙ケろことができる
。これらの基材は場合により、コロナ処理、シランカッ
プリング処理等の表面処理を行ってから用いることが出
来る。The polarizing plate of the present invention comprises: - A compound represented by formula (1) and (U) and/or
' or by coating a solution containing a compound represented by f, II, or l. “As the base material used for the polarizing plate of the present invention, in addition to glass, triacetyl cellulose film (hereinafter referred to as TAC film)
, diacetyl cellulose film, cellulose acetate film, polyester film, vinyl chloride film, polystyrene film, polypropylene film, polyamide film, polyethylene film, polyether sulfone film, acryl-based film, etc., among which preferred ones are used. For T, examples include 〇 film, polyester film, etc. These base materials can be used after surface treatment such as corona treatment and silane coupling treatment, depending on the case.
ラビング剤としては、布、紙、皮革、綿、フェルト、パ
フ等を、場合によりクレー、ジルコニア、アルミナ等の
研磨剤と共に用いることが出来る。また、ラビングの程
度はラビング剤によって異なるが、ラビングの回数は１
〜３０回が望ましい。As the rubbing agent, cloth, paper, leather, cotton, felt, puff, etc. can be used together with an abrasive agent such as clay, zirconia, alumina, etc., depending on the case. Also, the degree of rubbing varies depending on the rubbing agent, but the number of times of rubbing is 1
~30 times is desirable.
式（１）で表される化合物と式（ＩＩ）及び／又は式（
１）で表される化合物を溶かすための溶剤としては水及
び水と混合しうる有機溶剤類が適し、その具体例として
は、水、メチルアルコール、エチルアルコール、イソプ
ロピルアルコール、エチレングリコール等のアルコール
類、メチルセロソルブ、エチルセロソルブ等のセロソル
ブ類、アセトン、ジメチルホルムアミド等の単独又は二
種以上の混合溶剤を挙げることが出来る。A compound represented by formula (1) and formula (II) and/or formula (
As the solvent for dissolving the compound represented by 1), water and organic solvents that are miscible with water are suitable; specific examples include water, alcohols such as methyl alcohol, ethyl alcohol, isopropyl alcohol, and ethylene glycol. , cellosolves such as methyl cellosolve and ethyl cellosolve, acetone, dimethylformamide and the like alone or in combination of two or more solvents.
式（１）で表される化合物と式（ＩＩ）及び／又は式（
Ｍｌで表される化合物を溶解すべき濃度は溶媒忙より異
なるが、０．５〜１０％が望ましい。更に、場合により
界面活性剤等の添加剤を加えることが出来る。A compound represented by formula (1) and formula (II) and/or formula (
The concentration at which the compound represented by Ml should be dissolved varies depending on the solvent content, but is preferably 0.5 to 10%. Furthermore, additives such as surfactants may be added depending on the case.
式（１）で表される化合物と式（ｉｔ）及び／′又は式
（Ｉｆｆ）で表される化合物溶液を基材に塗布する塗布
法としては例えば、バーコーター、スプレー、ロール等
のコート法にて塗布出来る。コート時の温度は通常Ｏ〜
８０℃、好ましくは２５〜４０℃である。乾燥温度は２
５〜１２０℃、好ましくは５０〜８０℃である。Examples of coating methods for applying a solution of the compound represented by formula (1) and the compound represented by formula (it) and/' or formula (Iff) to a substrate include coating methods such as bar coater, spray, and roll coating methods. Can be applied at. The temperature during coating is usually O~
The temperature is 80°C, preferably 25-40°C. The drying temperature is 2
The temperature is 5 to 120°C, preferably 50 to 80°C.
このようにして製造された偏光板はそのまま使用される
他、耐久性を要求される分野においてはポリエステル、
塩化ビニール、トリアセチルセルローズ、アクリル樹脂
、ポリエーテルスルホン等の支持フィルムを接着したり
、特殊アクリル樹脂等でコーティングして高耐久性の偏
光板として使用に供される。Polarizing plates manufactured in this way can be used as is, and in fields where durability is required, polyester,
It can be used as a highly durable polarizing plate by adhering a supporting film such as vinyl chloride, triacetylcellulose, acrylic resin, or polyether sulfone, or by coating it with a special acrylic resin.
本発明の偏光板は各種デイスプレィ、装飾材料、透過防
止、フィルター等に用いることができる。The polarizing plate of the present invention can be used for various displays, decorative materials, transmission prevention, filters, etc.
以下実施例により本発明を更に詳しく説明する。尚、実
施例において部は重量部をあられしスルホン酸基は遊離
酸の形で表すものとする。The present invention will be explained in more detail with reference to Examples below. In the examples, parts are by weight, and sulfonic acid groups are expressed in the form of free acids.
また、ＳはＳ ０３ Ｈを表すものとする。なお波長３
８０〜７０００ｍの範囲で求めた三刺激値のＹ値で表し
、単板の場合なＹ＋ （視感透過率）、二枚を平行位に
配した場合をＹ／／、二枚を直行位に配した場合をＹ工
で表すと、平均偏光率ρはＹ／／、ＹＬを用いて次式に
よって定義される。Further, S represents S 03 H. Furthermore, wavelength 3
It is expressed as the Y value of tristimulus values obtained in the range of 80 to 7000 m, Y+ (luminous transmittance) for a single plate, Y// for two plates arranged in parallel, and Y// for two plates arranged in perpendicular position. When the case where Y is arranged is expressed as Y, the average polarization rate ρ is defined by the following equation using Y// and YL.
実施例１゜
水１００部に
非イオン性界面活性剤エマルゲン９２０（化工アトラス
社製）０．０５部を加え、加熱溶解後冷却し、濾過して
不溶解分を除去することにより染料溶液を得た。Example 1 0.05 part of the nonionic surfactant Emulgen 920 (manufactured by Kako Atlas Co., Ltd.) was added to 100 parts of water, dissolved by heating, cooled, and filtered to remove insoluble matter to obtain a dye solution. Ta.
ＴＡＣフィルム（厚さ８０μ）の全面を縦方向にフェル
トで１０回ラビングし、その後一定間隔で横方向に２０
回ラビングした後、水洗、乾燥した。Rub the entire surface of the TAC film (thickness 80μ) 10 times in the vertical direction with felt, then rub it 20 times in the horizontal direction at regular intervals.
After rubbing twice, it was washed with water and dried.
得られたフィルム上に前記染料溶液をバーコーターで塗
布した後、６０℃で乾燥することによって偏光板を得た
。このものはデイスプレーとして用いられる。The dye solution was applied onto the obtained film using a bar coater, and then dried at 60°C to obtain a polarizing plate. This item is used as a display.
得られた偏光板の視感透過率Ｙｄ家３６．０％、平均偏
光率ρは８０．０％であった。The luminous transmittance Yd of the obtained polarizing plate was 36.0%, and the average polarization ratio ρ was 80.0%.
実施例２゜
水９５部、インプロビルアルコール５部の混合溶媒に
非イオン性界面活性剤エマルゲン９２０（化工アトラス
社製）０．０５部を加え、加熱溶解後冷却し、濾過して
不溶解分を除去することにより染料溶液を得た。Example 2゜0.05 part of the nonionic surfactant Emulgen 920 (manufactured by Kako Atlas Co., Ltd.) was added to a mixed solvent of 95 parts of water and 5 parts of Improvil alcohol, dissolved by heating, cooled, and filtered to remove the insoluble matter. A dye solution was obtained by removing.
ＴＡＣフィルム（厚さ８０μ）の全面を縦方向に工業用
ワイピング材キムワイプ（十條キンバリー社製、ワイパ
ーＳ−２００）でラビングし、その後一定間隔で横方向
にラビングした後、水洗、乾燥した。得られたフィルム
上に前記染料溶液をバーコーターで塗布した後、６０℃
で乾燥することによって偏光板を得た。The entire surface of the TAC film (thickness: 80 μm) was rubbed in the vertical direction with an industrial wiping material Kimwipe (manufactured by Jujo Kimberly Co., Ltd., Wiper S-200), then laterally rubbed at regular intervals, washed with water, and dried. After coating the dye solution on the obtained film with a bar coater, the film was heated at 60°C.
A polarizing plate was obtained by drying.
得られた偏光板の視感透過率Ｙ１は３７．３％、平均偏
光率ρは８１．０％であった。The luminous transmittance Y1 of the obtained polarizing plate was 37.3%, and the average polarization rate ρ was 81.0%.
実施例３゜
水１００部に
非イオン性界面活性剤エマルゲンＬ−７０（化工アトラ
ス社製）０．０５部を加え、加熱溶解後冷却し濾過して
不溶解分を除去することにより染料溶液を得た。Example 3 A dye solution was prepared by adding 0.05 part of a nonionic surfactant Emulgen L-70 (manufactured by Kako Atlas Co., Ltd.) to 100 parts of water, heating and dissolving it, then cooling and filtering to remove insoluble matter. Obtained.
ＴＡＣフィルム（厚さ８０μ）の全面を実施例２と同様
にラビングした後、水洗、乾燥した。得られたフィルム
上に前記染料溶液をバーコーターで塗布した後、熱風ド
ライヤーで４０℃で乾燥することによって偏光板を得た
。The entire surface of the TAC film (thickness: 80 μm) was rubbed in the same manner as in Example 2, then washed with water and dried. The dye solution was applied onto the obtained film using a bar coater, and then dried at 40°C using a hot air dryer to obtain a polarizing plate.
得られた偏光板の視感透過率Ｙ、は４１．０％、平均偏
光率ρは８３．０％であった。The luminous transmittance Y of the obtained polarizing plate was 41.0%, and the average polarization rate ρ was 83.0%.
実施例４
水１００部に
Ｓ Ｓ
非イオン性界面活性剤エマルゲンＬ−７０（化工アトラ
ス社製）０．０５部を加え、加熱溶解後冷却し濾過して
不溶尊公を除去することにより染料溶液を得た。Example 4 A dye solution was prepared by adding 0.05 part of S S nonionic surfactant Emulgen L-70 (manufactured by Kako Atlas Co., Ltd.) to 100 parts of water, dissolving it by heating, cooling and filtering to remove insoluble particles. I got it.
ＴＡＣフィルム（厚さ８０μ）の全面を実施例２と同様
にラビングした後、水洗、乾燥した。得られたフィルム
上に前記染料溶液をバーコーターで塗布した後、６０℃
で乾燥することによって偏光板を得た。The entire surface of the TAC film (thickness: 80 μm) was rubbed in the same manner as in Example 2, then washed with water and dried. After coating the dye solution on the obtained film with a bar coater, the film was heated at 60°C.
A polarizing plate was obtained by drying.
得られた偏光板の視感透過率Ｙ、は４００％、平均偏光
率ρは８３．５％であった。The luminous transmittance Y of the obtained polarizing plate was 400%, and the average polarization rate ρ was 83.5%.
実施例５〜実施例１９゜
・実施例３において使用する染料の種類及びそれらの使
用量を表に示された「染料構造」及び「使用量」に代え
る他は実施例３と同様に処理して偏光板を得た。そして
それら視感透過率及び平均偏光率をそれぞれ「透過率」
及び「偏光率」として表に示した。Examples 5 to 19゜Processed in the same manner as in Example 3, except that the types of dyes used in Example 3 and their amounts used were replaced with the "dye structure" and "amount used" shown in the table. A polarizing plate was obtained. The luminous transmittance and average polarization rate are respectively called "transmittance".
and shown in the table as "polarization rate".
発明の効果
偏光軸が任意の方向に、かつ連続的にパターン化された
高い偏光率を有する偏光板が容易にかつ安価に製作出来
るようになった。Effects of the Invention It has become possible to easily and inexpensively produce a polarizing plate with a high polarization index and whose polarization axis is continuously patterned in any direction.
Claims (1)
ルコキシ基又はスルホン酸基で置換されていてもよいフ
ェニル基を、Ａ＿２はスルホン酸基で置換されていても
よいフェニル基を、Ｒ＿１とＲ＿４は水素原子、水酸基
又は低級アルコキシ基を、Ｒ＿２、Ｒ＿３、Ｒ＿５、Ｒ
＿６はそれぞれ独立に水素原子、水酸基又はスルホン酸
基を、Ｒ＿７は水素原子、メチル基又は置換されていて
もよいフェニル基をそれぞれ表す。〕 で表される化合物と下記式（II）及び／又は（III）▲
数式、化学式、表等があります▼（II） 〔式（II）において、Ｒ＿８、Ｒ＿９は互いに独立して
水素原子、メチル基、メトキシ基又はスルホン酸基を、
Ｂは水酸基、スルホン酸基又はアミノ基で置換されたナ
フチル基をそれぞれ表す。〕 ▲数式、化学式、表等があります▼（III） 〔式（III）において、Ｃは水酸基、アミノ基又はスル
ホン酸基で置換されていてもよいナフチル基を、Ｄは低
級アルキル基、低級アルコキシ基、水酸基若しくはスル
ホン酸基で置換されていてもよいフェニレン基又はナフ
チレン基を、Ｒ＿１＿０は水素原子、メチル基、アセチ
ル基、カルバモイル基、置換されていてもよいフェニル
基又はベンゾイル基をそれぞれ表す。〕で表される化合
物との混合物を塗布してなる偏光板。[Claims] 1. The following formula (1) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (1) [In formula (1), A_1 is substituted with a lower alkyl group, a lower alkoxy group, or a sulfonic acid group. A_2 is a phenyl group which may be substituted with a sulfonic acid group, R_1 and R_4 are hydrogen atoms, hydroxyl groups or lower alkoxy groups, R_2, R_3, R_5, R
_6 each independently represents a hydrogen atom, a hydroxyl group, or a sulfonic acid group, and R_7 represents a hydrogen atom, a methyl group, or an optionally substituted phenyl group, respectively. ] A compound represented by the following formula (II) and/or (III) ▲
There are mathematical formulas, chemical formulas, tables, etc. ▼ (II) [In formula (II), R_8 and R_9 independently represent a hydrogen atom, a methyl group, a methoxy group, or a sulfonic acid group,
B represents a naphthyl group substituted with a hydroxyl group, a sulfonic acid group, or an amino group, respectively. ] ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (III) [In formula (III), C is a naphthyl group which may be substituted with a hydroxyl group, an amino group or a sulfonic acid group, and D is a lower alkyl group or a lower alkoxy group. R_1_0 represents a hydrogen atom, a methyl group, an acetyl group, a carbamoyl group, an optionally substituted phenyl group or a benzoyl group, respectively. A polarizing plate coated with a mixture of compounds represented by ].
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63093379A JP2568882B2 (en) | 1988-04-18 | 1988-04-18 | Polarizer |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63093379A JP2568882B2 (en) | 1988-04-18 | 1988-04-18 | Polarizer |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01265205A true JPH01265205A (en) | 1989-10-23 |
| JP2568882B2 JP2568882B2 (en) | 1997-01-08 |
Family
ID=14080671
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63093379A Expired - Fee Related JP2568882B2 (en) | 1988-04-18 | 1988-04-18 | Polarizer |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2568882B2 (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998044051A1 (en) * | 1997-03-31 | 1998-10-08 | Nippon Kayaku Kabushiki Kaisha | Water-soluble disazo compounds, water-base ink composition, and colored object |
| EP1975686A2 (en) | 2007-03-30 | 2008-10-01 | FUJIFILM Corporation | Liquid crystal display provided with an optical phase retarder |
| WO2012165224A1 (en) * | 2011-05-31 | 2012-12-06 | 日本化薬株式会社 | Dye-based polarizing element and polarizing plate |
| EP2641940A1 (en) * | 2012-03-22 | 2013-09-25 | ILFORD Imaging Switzerland GmbH | Water soluble and water fast dyes for ink jet printing |
| WO2014156852A1 (en) * | 2013-03-28 | 2014-10-02 | 日本化薬株式会社 | Tetrakis-azo compound for black colors, dye composition including same, and dyeing method using same |
| WO2020230647A1 (en) * | 2019-05-13 | 2020-11-19 | 日本化薬株式会社 | Achromatic polarizer, achromatic polarizing plate using same, and display device |
-
1988
- 1988-04-18 JP JP63093379A patent/JP2568882B2/en not_active Expired - Fee Related
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998044051A1 (en) * | 1997-03-31 | 1998-10-08 | Nippon Kayaku Kabushiki Kaisha | Water-soluble disazo compounds, water-base ink composition, and colored object |
| EP1975686A2 (en) | 2007-03-30 | 2008-10-01 | FUJIFILM Corporation | Liquid crystal display provided with an optical phase retarder |
| JPWO2012165224A1 (en) * | 2011-05-31 | 2015-02-23 | 日本化薬株式会社 | Dye-type polarizing element and polarizing plate |
| WO2012165224A1 (en) * | 2011-05-31 | 2012-12-06 | 日本化薬株式会社 | Dye-based polarizing element and polarizing plate |
| EP2641940A1 (en) * | 2012-03-22 | 2013-09-25 | ILFORD Imaging Switzerland GmbH | Water soluble and water fast dyes for ink jet printing |
| WO2013139485A1 (en) * | 2012-03-22 | 2013-09-26 | Ilford Imaging Switzerland Gmbh | Water soluble and water fast dyes for ink jet printing |
| CN104379678A (en) * | 2012-03-22 | 2015-02-25 | 莱克斯-托恩工业有限公司 | Water soluble and water fast dyes for ink jet printing |
| JP2015514137A (en) * | 2012-03-22 | 2015-05-18 | レックス−トーン・インダストリーズ・リミテッド | Water-soluble and water-resistant dyes for inkjet printing |
| US9499707B2 (en) | 2012-03-22 | 2016-11-22 | Rex-Tone Industries Ltd | Water soluble and water fast dyes for ink jet printing |
| CN104379678B (en) * | 2012-03-22 | 2017-07-18 | 莱克斯-托恩工业有限公司 | Inkjet printing water solubility and water resistance dyestuff |
| WO2014156852A1 (en) * | 2013-03-28 | 2014-10-02 | 日本化薬株式会社 | Tetrakis-azo compound for black colors, dye composition including same, and dyeing method using same |
| JPWO2014156852A1 (en) * | 2013-03-28 | 2017-02-16 | 日本化薬株式会社 | Tetrakisazo compound for black, dye composition containing the same, and dyeing method using the same |
| CN105102546B (en) * | 2013-03-28 | 2017-03-08 | 日本化药株式会社 | Black with four azo-compounds, comprise its dye composite and use its colouring method |
| WO2020230647A1 (en) * | 2019-05-13 | 2020-11-19 | 日本化薬株式会社 | Achromatic polarizer, achromatic polarizing plate using same, and display device |
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|---|---|
| JP2568882B2 (en) | 1997-01-08 |
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