JPS5941383A - Photochromic composition - Google Patents

Abstract

PURPOSE:To provide titled composition of high durability, capable of color development and fading within a few seconds when irradiating and shielding a light, particularly sunlight, respectively, comprising a condensed polynuclear aromatic compound and specific resin medium. CONSTITUTION:The objective composition comprising (A) 1l of a benzene ring- contg. resin medium free from both heteroatom and multiple bond [pref. polystyrene, poly-p-xylylene, polymethylstyrene (among others, polystyrene, because of low cost, colorless and clear, and outstanding molding processability)] and (B) pref. 5X10<-3>-1X10<-2>mol of a condensed polynuclear aromatic compound (e.g., 3,4-5,6-7,8-12,13-tetrabenzoperopyrene of formula).

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a photochromink composition containing a fused polycyclic aromatic compound, and particularly to a photochromink composition comprising a fused polycyclic aromatic compound and a resin medium in which it is molecularly dispersed.

In the present invention, when irradiated with light, the term 7 otochromink composition develops or changes color under the influence of light of a certain wavelength, and when brought to a dark place, it returns to a colorless state or a color different from that at the time of irradiation with light. Used for material systems. In addition, the term fused polycyclic aromatic compound does not refer to S-membered rings, 7-membered rings, etc., but is used for fused polycyclic aromatic IN compounds consisting only of O@ rings, but does not refer to S-membered rings, 7-membered rings, etc. May contain.

There has been extensive research on photochromic compounds;
゛Spiropyran is limited to 5H organic compounds.

Triphenylmethane dye leuco, imidazole.

Indico, thioindico, dinitrobenzyl, pyridine, fluquito, stilbene, heterocyclic compounds.

Condensed polycyclic aromatic compounds are being studied.

Particularly regarding spiropyran, many studies have been conducted in liquids and resins, and applications have been attempted, but there is a problem that the durability is not very good. Regarding fused polycyclic aromatic compounds, 118 studies have been conducted on systems in which they are dispersed in various resin media such as epoxy resins, polyvinyl chloride, polymethyl methacrylate, and polycarbonate. (Special UH Showa lter//1I4133, Japanese Patent Publication Showa ss-1
sistza) However, the first scene is IRI QJ +
a m 7 o'clock, the color develops and discolors repeatedly within a few seconds, and the fruit moon j
A photochromic composition with good viscosity and durability has not yet been reported.

The purpose of the present invention is to provide a highly durable 7A advantageous composition that develops and discolors within a few seconds when exposed to or interrupted by light, especially sunlight. be done.

That is, the present invention is a photochromic composition comprising a fused polycyclic aromatic compound and a resin medium containing a benzene ring and containing no heteroatoms or multiple bonds.

In the present invention, the fused polycyclic aromatic compound is molecularly dispersed in a resin medium, and the rate of color development, fading, or discoloration due to changes in electronic state due to light irradiation, such as sunlight irradiation, is extremely fast. Within a few seconds. The irradiated light may include at least ultraviolet light and visible light, and examples include sunlight, xenon lamp light, carbon arc lamp light, and mercury lamp light.

Examples of the fused polycyclic aromatic compounds in the present invention are as follows.

/, +2-3, +-dibenzanthracene.

Pisen.

3,'l-benzotetrafen.

/, 2-6.7-dibencypyrene.

8, 2-3. ! -j, 4;-tribenzanthracene.

/, 2-benzocoronene.

8/, 2-2.3-IO, //-)ribenzoperylene.

/, +2-! ;, g-dibenzocoronene.

/, 2-3.11-! ;, 1. −) Ribenzocoronene.

/,,2-3. 'l-4,7-7,2,/3-tetrabenzopentacene.

/, 2-3.11-5+Otsu-7, Za-tetrabenzanthracene.

3.11-s, Otsu-7, g-/+2. /3-tetrabenzoberopyrene.

/ r+23 *Q 3 +6-7, Za-ta, 10-/
2. /3-hexabenzoperopyrene.

Chrysene, coronene, etc., which are condensed polycyclic aromatic compounds with a relatively small degree of condensation (number of benzene rings), develop color when irradiated with very strong light, but do not develop or change color when irradiated with sunlight. In order to develop or change color upon irradiation with sunlight, it is preferable to use a compound that has a degree of condensation that is greater than a certain level and has at least the number of benzene rings.Condensed 1η
Is A relatively large? i Polycyclic aromatic fIs compound has a methyl group, fluorine, etc. 1? Even if it contains a substituent, sunlight I
(Color develops or changes color at f'74.

If the resin medium is one that disperses the fused polycyclic aromatic compound in molecular form, the photochromic composition will exhibit the A tochromic phenomenon; In order to improve the durability of the photochromic composition consisting of a compound and a resin medium, it contains a benzene ring, a heteroatom and a multi-l! Polystyrene is a bond-free layer.

Polyparaxylylene and polymethylstyrene are preferred.

The benzene ring contained in the resin medium increases the affinity with the condensed polycyclic aromatic compound and helps to disperse this compound uniformly and widely in the medium.

The resin medium is epoxy resin and polyvinyl chloride.

Unlike polymethyl methacrylate and polycarbonate, it does not contain any heteroatoms or multiple bonds, so it has low reactivity with the condensed polycyclic aromatic compound dispersed therein, which reduces the durability of the photochromink composition. Useful for increasing sexuality. Among these resin media, polystyrene is optimal because it is inexpensive, colorless and transparent, and has excellent moldability.

The blending ratio of the condensed polycyclic aromatic compound and the resin medium is usually /X10-7 to /X/ with respect to the resin body/liter.
in the range of 1-' mol, particularly preferably from tXlo-3 to
The condensed polycyclic aromatic compound in the range of /

According to the present invention, irradiation with light, such as sunlight, which has not been available in the past,
A highly durable photochromic composition that develops, fades, or changes color within a few seconds upon interruption is obtained. This photochromic composition exhibits its function when irradiated with light including at least ultraviolet light and visible light, and therefore, its ability to develop or change color when exposed to sunlight, which is natural light, has important industrial significance. . For example, for plastic lenses, plastic windows for buildings, automobiles, aircraft, etc.
The intensity of the tl+ + photochromic material of the present invention for decoration.
J. Mick introduction products can be used. Others
<Device 1 It can be applied to safety glasses for high-intensity light, devices for measuring light intensity, etc. Furthermore, compared to spiropyran and the like, fused polycyclic aromatic compounds are extremely stable thermally, so they are advantageous when it is necessary to apply heat for kneading into a resin medium, molding, etc.

The present invention will be explained in more detail with reference to Examples below.
It goes without saying that this does not limit the scope of the present invention.

Examples/Known methods such as JP-A-Sho,! ;! is a compound of the following formula (1) by the method described in ;-/3/3g,
,? , 4'-t, Otsu-71za-ii, /,? -Tetrabenzoperopyrene was synthesized.

Compound (1) 0. A pellet of polystyrene (manufactured by Mitsui Toatsu Chemical Co., Ltd.) of 7.0 mm was placed in a Pyrex glass tube with an outer diameter of 7.2 mm and an inner diameter of 9 mm, and the mixture was vigorously shaken. Approximately 7 (79 f2 mm under reduced pressure of H9) in the vacuum line
It was heated at 0°C for S hours and sealed into a tube under reduced pressure.

The sample in the glass tube was virtually colorless and transparent in the shade.

When exposed to sunlight, it developed a green color in about a second, and when placed on a parrot, the color disappeared within a few seconds. This sample K'l 1.
Xenon lamp with an intensity of mW10m2 (UX made by Ushio)
L! ;0O8) When irradiated with light, it developed a green color.

This sample was continuously irradiated with xenon lamp light.

Another similar sample was subjected to intermittent irradiation of /min irradiation and interruption /j seconds. When both samples were subjected to continuous irradiation or intermittent irradiation for 1 hour and then blocked from sunlight, both samples showed the same color development and fading as at the initial stage.

Example) A compound represented by the following formula (II) was prepared by a known method/, 2-3. 'l-5. A-7, Za-9, 70-
/, 2. /3-hexahenzoperobylene was synthesized. A sample similar to Example 1 was prepared using polystyrene (manufactured by Mitsui Toatsu Chemical Co., Ltd.) as the resin medium.

In the 1-1 shade, it was substantially colorless and transparent. When exposed to sunlight, it developed a bluish-green color in about a second, and when placed in the shade, the color disappeared within a few seconds. When irradiated with xenon lamp light of 1'l m W/0 m2, a bluish-green color developed.

Before irradiation with xeno lamp light similar to Example/, irradiation with sunlight,
When the light was cut off, the same coloring and fading as before the xeno lamp light irradiation was repeated.

Comparative Example A sample similar to Example was prepared using polymethyl methacrylate (manufactured by Sumitomo Chemical) in place of the polystyrene used in Example. When exposed to sunlight, it turned green. As in Example 1, after continuous irradiation with xenon lamp light for 10 hours and heat irradiation for 1 lyi, irradiation with sunlight and blocking were performed, and none of the samples developed a green color.

Comparative Example 2 When an experiment similar to Comparative Example 2 was conducted using Compound (I) and polyester (manufactured by Nippon Gosei Ka), it deteriorated under light 4-J between xenon lamp light 101-1.

Claims (1)

[Claims] (1) From a fused polycyclic aromatic compound and a resin medium containing a benzene ring and not containing a J bond and a polycyclic aromatic compound. 7. The Otochrominok composition as set forth in claim 8, wherein the opposite medium is at least one unique J8J resin selected from polystyrene, polyparaxylylene, and polymethylstyrene.