JPS61263958A - Far infrared ray absorbing azo compound - Google Patents

Abstract

NEW MATERIAL:A compound shown by the formula I (M is H, alkali metal or alkaline earth metal; X is lower alkoxy; Y is H or lower alkyl; Z is alkyl or aralkyl). USE:A far infrared ray absorber. Capable of forming a thin film having a uniform composition in good reproducibility, useful as a dyestuff for an optical recording having high stability to light and heat. Since the compound has absorption wavelength reaching a visible light range and light screening action on wavelength from visible light range to far infrared ray range and is useful as a remote control device for TV, etc., speed and distance measurement of camera, etc., an optical filter for preventing malfunction caused by visible light rays having vigrous change in light volume of receptor element in game machine, etc. PREPARATION:A compound shown by the formula II is tetrazotized, reacted with m-phenylenediamine to give a compound shown by the formula III, which is alkylated with an alkyl halide or aralkyl halide to give a compound shown by the formula I.

Description

DETAILED DESCRIPTION OF THE INVENTION (1) Industrial Application Field The present invention relates to a novel azo compound having absorption in the near-infrared region.

In recent years, the use of near-infrared rays has attracted attention in a wide range of fields, and for example, optical discs such as compact discs and video discs that utilize laser light as a light source are being developed for optical recording in the information field. A near-infrared absorber may be used as the main material or medium of the recording element in the optical disc. One of the principles is to form a laser beam absorption layer on the substrate,
A laser beam corresponding to light or sound is irradiated and recorded (written) as a signal. This change in the absorption layer (recording layer) is again read as a signal using a laser beam, which is then converted into sound or light and reproduced. Therefore, the role of the near-infrared absorber present in this recording layer is one of the most important elements, which has the effect of efficiently absorbing laser light and enhancing thermal effects.

(2) Prior Art Known near-infrared absorbers used in conventional recording layers include Ta, In, Bi, C52-Te, Te-C,
Examples of inorganic metal complexes such as TeOx, metal complexes described in Japanese Patent Publication No. 46-3452, and dye-based ones include 3.
One example is 3'-dimethyloxatrylpocyanine iodide, but in the case of inorganic metals, special equipment is required to form a thin film of the recording layer on the substrate using a vacuum evaporation method. The issue of toxicity cannot be ignored either.

Further, in the case of metal complexes, they have a small extinction coefficient and must be used in large quantities, and they also have poor solubility or compatibility in solvents, resins, etc., and are not sufficiently stable.

On the other hand, although the dye type has a large extinction coefficient, it has poor heat resistance and has not been found to be of any practical use.

(3) Problems to be solved by the invention The desired performance of the near-infrared absorber as a recording layer material is that a thin film with a uniform composition can be formed with good reproducibility, and high stability (research, heat resistance, etc.) , high sensitivity, uniformity of recording pit shape, etc.

(4) Means for solving the problem As a result of studying azo compounds as near-infrared absorbing compounds, the present inventors found that among the compounds shown in formula (I), compounds with excellent near-infrared absorption were found. This heading led to the present invention.

General formula (I)' (wherein, Ml and H, an alkali metal or alkaline earth metal, X represents lower alkoxy, Y represents H or lower alkyl, and 2 represents alkyl or aralkyl.) In this general formula CI) The azo compound represented can be produced by the following steps. For example, an azo dye represented by general formula (TI) (where M, X, and Y are as defined in formula (I)) is tetrazotized by a conventional method,
■-By reacting with phenylene diamine, the formula (m) (in the formula,
In the formula, M, X, and Y are as defined in formula (I). ) and can be obtained by alkylating formula (m) with an alkyl halide or an aralkyl halide.

As the azo compound of the general formula (H) used in the present invention, it is important that X is methoxy or ethoxy, and Y is 11 or methyl. In addition to being represented by H, H in the azo compound of general formula (II) may be an alkali metal or an alkaline earth metal depending on the process leading to formula (III) or the method of purification treatment. Examples of the alkylating agent of formula (III) include benzyl chloride, p-isopropylbenzyl chloride, P-isododecylbenzyl chloride, n-octyl bromide, and n-dodecyl bromide.

(5) Actions and Effects Next, the excellent near-infrared absorption performance of the azo compound represented by the general formula (I) will be explained.

That is, the azo compound represented by the above general formula (■) is 70
It has a maximum absorption wavelength in the wavelength range of 0 to 900 nm, a molecular extinction coefficient of 30,000 or more, excellent heat resistance, solubility in various solvents, and compatibility with various resins.
It was found to be useful as an optical recording dye.

In addition, the azo compound shown in the above general formula (I) has an absorption wavelength range that extends to the visible range, and it goes without saying that it is useful as a filter for light shielding at wavelengths from the visible range to the near-infrared range. do not have. For this purpose, for example, it is used to measure the speed and distance of electrical appliances, especially remote control devices such as televisions, radios, and stereos, cameras and projectors, or to prevent malfunctions of light receiving elements in game machines and automatically opening/closing doors due to light in the visible region, where the light dose changes rapidly. Extremely useful for light incident filters.

(6) Examples The present invention will be explained in detail below using examples.

Example 1 16.1 g of a disazo compound represented by the following formula (IV) '+031i was dissolved in 400 ml of water to pH 9 using caustic soda, and then 4.3 g of sodium nitrite was mixed and dissolved therein. Add this to ice water containing 8.5g of hydrochloric acid.
The mixture was poured into a 40ml volume and stirred at about 5°C for 2 hours to form tetrazotization. After neutralizing to pH 5 to 6, about 50 ml of an aqueous solution containing 6.5 g of metaphenylenediamine was injected, the pH was adjusted to 7 to 8 with soda ash, and the mixture was stirred for about 4 hours. Inorganic salts were removed using a water filtration method, and impurities were removed into the filtrate by washing with methanol to obtain 90 g of a paste of a tetrakisazo compound represented by formula (V).

30 g of the azo compound paste of formula (V) was dispersed in 140 ml of water, and the pH was adjusted to 8.5 with soda ash at about 50°C, and then 28 ml of dimethylformamide was added to give a pH of 90 to 9.
Heated to 5°C. After alternately adding 6.5 g of p-isododecylbenzyl chloride and 2.5 g of soda ash, the pH was adjusted to 8.
, 5 to 9, and heated at 90 to 95° C. for about 3 hours.

The reaction product was cooled, filtered, washed with water and dried. 9 g of black powder was obtained. This product had the structure shown below and showed good solubility in various organic solvents. The maximum absorption wavelength in dimethylformamide is 735 nm.

Example 2 In Example 1, 3.7 g of p-isopropylbenzyl chloride was used instead of 6.5 g of p-isododecylbenzyl chloride to obtain 8 g of black powder having the structure of the following formula. Maximum absorption wavelength in dimethylformamide is 735
It is nm.

Example 3 In Example 1, 2.8 g of benzyl chloride was used instead of 6.5 g of p-isododecylbenzyl chloride to obtain 6 g of a black powder having the following formula structure. The maximum absorption wavelength in dimethylformamide was 735 nm. Examples 4 to 6 Azo compounds of the present invention having the structures shown in Table 1 were obtained in the same manner as in Example 1. Dimethylformamide = 8-

[Brief explanation of the drawing]

Figure 1 Visible and near-infrared absorption curve of Example 1 Figure 2 Visible and near-infrared absorption curve of Example 2 Figure 3 Visible and near-infrared absorption curve of Example 3 Figure 4 Infrared absorption curve of Example 1 Figure 5 Infrared absorption curve of Example 2 Figure 6 Infrared absorption curve of Example 3 Patent applicant: Taoka Chemical Industry Co., Ltd. =10=

Claims (1)

[Claims] The following general formula (I) ▲Mathematical formulas, chemical formulas, tables, etc.▼(I) (In the formula, M is H, an alkali metal or alkaline earth metal, X is lower alkoxy, Y is H or lower alkyl,
A near-infrared absorbing azo compound represented by Z (Z represents alkyl or aralkyl).