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Azo compound and dye polarizing film containing the same

a technology of polarizing film and compound, which is applied in the direction of polarizing elements, instruments, disazo dyes, etc., can solve the problems of insufficient light resistance, heat resistance, and wet heat resistance of dye-containing polarizing elements, and achieve excellent polarization performance and resistance to humidity, heat and light, and high performance. , the effect of excellent polarization performance and resistan

Inactive Publication Date: 2010-10-14
NIPPON KAYAKU CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0010]An object of the present invention is to provide a polarizing plate of high performance having excellent polarization performance and resistance to humidity, heat, and light. Further, another object of the present invention is to provide a polarizing plate of high performance which does not cause color leakage at the perpendicular position in the wavelength range of visible light and which has excellent polarization performance and resistance to humidity, heat, and light, the polarizing plate being a neutral color polarizing plate produced by adsorbing two or more dichromatic dyes in a polymer film, followed by orientation thereof.
[0011]A further object of the present invention is to provide polarizing plates of high performance corresponding to three primary colors for a color liquid crystal projector, which are good in all of brightness, polarization performance, durability, and light resistance.

Problems solved by technology

On the other hand, this polarizing film is weak to moisture and heat, and when it is used for a long time under conditions of high temperature and high humidity, there arises a problem of durability.
However, the effects of these methods are not satisfactory.
On the other hand, a dye-containing polarizing film comprising a dichromatic dye as a polarizing element has better humidity resistance and heat resistance than an iodine polarizing film, but, generally, initial polarizing performance of the dye-containing polarizing element is insufficient.
However, as mentioned above, the iodine polarizing plate has a problem that its light resistance, heat resistance, and wet heat resistance are insufficient, because iodine is a polarizer.
Thus, there is a problem that to the demand of the marketplace for more brightness as in the color liquid crystal projector, the transmittance is still poor, and in order to realize brightness, it is necessary to increase intensity of the light source.
Furthermore, desire for further increase in brightness of a liquid crystal projector is strong and, as a result, the intensity of the light source used is inevitably growing stronger.
However, conventional polarizing plates containing the water soluble dyes have not yet satisfied the market needs sufficiently in terms of polarization characteristics, the range of absorption wavelength, hues, and the like.
Furthermore, among three polarizing plates corresponding to three primary colors for a color liquid crystal projector, namely, the plates for each of the blue channel, the green channel, and the red channel, none is good in all aspects of brightness, polarization performance, durability under conditions of high temperature and high humidity, and resistance to prolonged irradiation of light.

Method used

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  • Azo compound and dye polarizing film containing the same
  • Azo compound and dye polarizing film containing the same
  • Azo compound and dye polarizing film containing the same

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0051]27.7 parts of 4-(4′-aminophenyl)-azobenzenesulfonic acid were added to 500 parts of water and dissolved with sodium hydroxide. 32 parts of 35% aqueous hydrochloric acid were added thereto followed by addition of 6.9 parts of sodium nitrite and the mixture was stirred for one hour. Separately, 55 parts of the naphthol compound represented by the following formula (19) were added to 250 parts of a 20% pyridine aqueous solution and dissolved by making weakly alkaline with sodium carbonate. Subsequently, in this solution was introduced the diazotized product of the disazo compound obtained above with keeping the pH at 7 to 10, and the solution was stirred to complete the coupling reaction. Salting-out was carried out with sodium chloride and the precipitate was filtered to obtain 24.7 parts of the trisazo compound represented by the above formula (2). This compound had a reddish violet color and a maximum absorption wavelength at 542 nm in a 20% pyridine aqueous solution.

example 2

[0052]25.3 parts of the compound represented by the above formula (3) were obtained in the same manner as in Example 1, except that the naphthol compound represented by the above formula (19) used in Example 1 was replaced with the compound represented by the following formula (20). This compound had a violet color and a maximum absorption wavelength at 542 nm in a 20% pyridine aqueous solution.

example 3

[0053]27.7 parts of 4-(4′-aminophenyl)-azobenzenesulfonic acid were added to 500 parts of water and dissolved with sodium hydroxide. 32 parts of 35% aqueous hydrochloric acid were added thereto followed by addition of 6.9 parts of sodium nitrite and the mixture was stirred for one hour. 12.1 parts of 2,5-dimethylaniline dissolved in dilute hydrochloric acid water were added thereto and pH was adjusted to 3 by adding sodium carbonate while stirring at 30 to 40° C. The mixture was further stirred to complete the coupling reaction and 32.8 parts of the disazo compound represented by the following formula (21) were obtained.

[0054]In 600 parts of water were dispersed 40.9 parts of the disazo compound of the above formula (21), and then thereto were added 32 parts of 35% aqueous hydrochloric acid and then 6.9 parts of sodium nitrite, followed by stirring at 25 to 30° C. for 2 hours to perform diazotization. Separately, 34.5 parts of the naphthol compound represented by the following formu...

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Abstract

Disclosed is an azo compound represented by the formula (1) below, a salt thereof, or a copper complex salt compound thereof.(In the formula, R1 and R2 independently represent a hydrogen atom, a sulfonic acid group, a lower alkyl group or a lower alkoxyl group; R3-R6 independently represent a hydrogen atom, a lower alkyl group or a lower alkoxyl group; R7 represents a lower alkyl group or a lower alkoxyl group; and n represents 0 or 1.)

Description

TECHNICAL FIELD[0001]The present invention relates to a novel azo compound, a salt thereof or a copper complex salt compound thereof and a dye-containing polarizing film containing the same.BACKGROUND ART[0002]A polarizing plate having a function to transmit or shield light is a fundamental constituent element of a display device such as a liquid crystal display (LCD), along with liquid crystals which have a function of switching light. The area of application of this LCD has expanded broadly from small items such as an electronic calculator, a watch, and the like in the early day to a notebook computer, a word processor, a liquid crystal projector, a liquid crystal television, a car navigation system, indoor and outdoor measurement instruments, and the like. Also, the LCD is used in broad conditions from low to high temperature, from low to high humidity, and from low to high light intensity. Thus, a polarizing plate having high polarizing performance and excellent durability is de...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C09B31/08C09B31/22C09B45/28
CPCC09B31/08C09B31/22G02B5/3033C09B56/08C09B45/28C09K2323/031G02B5/30
Inventor SADAMITSU, YUICHIHIGETA, TAKAHIRO
Owner NIPPON KAYAKU CO LTD
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