JPH0396901A - Optical member made of polarizing resin with light control function - Google Patents

Abstract

PURPOSE:To enhance the repetitive durability of the color development effect at a high temp. and weatherability by providing a polarizing film and a light control function part contg. a specific org. photochromic material. CONSTITUTION:Any of the mode of sticking optical member elements 11, 12 to each other while holding the polarizing film P inserted therebetween, the mode of sticking the film P to one surface of a body 13 and the mode of polymerizing a monomer to embed the film P in the body 13 while holding the film P immersed into the material monomer at the time of forming the body 13 by cast polymerization is adopted. The light control layer C consisting of a resin contg. the spirooxadine compd. expressed by formula I is provided on the body 13 provided with the film P. In the formula I, R<1> denotes an alkyl group, allyl group, alkoxyalkyl group, substd. or unsubstd. alkyl group, substd. or unsubstd. aryloxyalkyl group; R<2> and R<3> respectively denote a substd. or unsubstd. alkyl group; R<4> to R<7> denote a hydrogen atom, halogen atom, alkyl group, alkoxy group, hydroxyl group, alkoxyalkyl group or substd. or unsubstd. amino group.

Description

DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a polarizing resin optical member having a light control function, particularly to a polarizing resin optical member used for polarizing lenses, sunglasses, goggles, and the like.

[Prior art]

In general, polarized lenses, sunglasses or goggles, etc.
It blocks the polarized light that occurs when natural light is reflected, thereby achieving an anti-glare or light-reducing effect.In recent years, these properties have been used to prevent polarization or glare, especially outdoors. For example, it can be used to prevent polarized light reflected from the snow surface when skiing, to prevent diffusely reflected light from the water surface when fishing, or as sunglasses to prevent dazzling for car drivers. It is used in a wide variety of applications, such as sunglasses and fashion lenses.

Conventional polarized lenses and sunglasses have the above-mentioned unique effects, but polarized lenses and sunglasses equipped with a polarizing film have a light attenuation rate determined by the characteristics of the polarizing film. Therefore, it is not possible to obtain a dimming function according to the intensity of incident light.

On the other hand, lenses and sunglasses made of resin have recently been widely used because of their features such as IN quantity, processability, and impact resistance. It was difficult to add functionality. That is,
Silver halide, which is commonly used to impart light control function to inorganic glass lenses, has poor compatibility with resins, and organic photochromic materials also have problems in terms of durability, degree of color development, speed of fading, etc. However, it has not always been possible to provide a resin optical member with a light control function.

For example, among various known organic photochromic compounds, spirooxazine compounds are known as having relatively good durability against repeated coloring action, such as those disclosed in Japanese Patent Publication No. 45-28892, Japanese Patent Publication No. 49-48631, JP-A-55-36284, JP-A-60-53
586, JP-A-61-53288, and JP-A-61-263982, 1,3.3-}
Limethylspiro[indoline-2,3'-(3H)naf31[2,1-bco(+.,4)oxazine] and its derivatives are disclosed.

However, conventional photochromic compositions containing spirooxazine compounds have had the problem of insufficient color development and, furthermore, low color development at high temperatures above room temperature.

Therefore, there has been a demand for a resin optical member that has both a polarizing function and a dimming function that are sufficient for light such as sunlight even in an outdoor natural environment.

However, in the past, no excellent resin optical member has been provided that can sufficiently and stably exhibit both of these functions over a long period of time.

[Problem to be solved by the invention]

The present invention meets the above-mentioned demands, and has a polarization function as well as a light control function using a specific organic photochromic substance, and has both excellent polarization and light control properties, and can be used at room temperature or higher. To provide a resin optical member that has excellent coloring property under high temperatures and repeated resistance to coloring action 4. Provides a resin optical member that has excellent durability and weather resistance, particularly a resin optical member that has such characteristics and is suitable for resin lenses, sunglasses, or goggles. The purpose is to

[Means to solve the problem]

The present polarizing resin optical member having a light control effect includes a resin optical member main body and a polarizing film, and contains at least one spirooxazine compound represented by the following general formula (I). It is characterized by having a dimming function part.

General formula (I) K+ (wherein R1 represents an alkyl group, an allyl group, an alkoxyalkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aryloxyalkyl group, R2 and R3 each represents a substituted or unsubstituted alkyl group, R4, R5, R6 and R7
each represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a hydroxyl group, an alkoxyalkyl group, or a substituted or unsubstituted amino group, and R4, R6 and R
7 may be plural. ) [Effects of the Invention] The polarizing resin optical member having a light control function according to the present invention not only has a polarizing effect due to a polarizing film but also has a light control function part containing a unique organic photochromic material, so that the incident light is The amount of light can be adjusted depending on the strength of the light, and it has both anti-glare and dimming effects, making it very useful from the viewpoint of protecting the eyes. Moreover, since the light control function part contains an organic photochromic substance made of a specific spirooxazine compound, the resin optical member of the present invention has color-forming properties and color-forming effects at room temperature or higher temperatures. It has excellent repeated durability and also has excellent weather resistance.

[Specific description of the invention]

The material of the optical member main body used in the present invention is not particularly limited as long as it is a resin, and resin materials used for ordinary resin lenses, sunglasses, goggles, etc. can be used. Specific examples include allyl carbonates of polyols such as diethylene glycol bisallyl carbonate, acrylic resins, cellulose resins, polyvinyl alcohol, polyvinyl acetate, polyurethane, epoxy resins, silicone resins, polystyrene, polyesters such as polyethylene terephthalate, and polyvinyl butyral. , polyamide, polyvinyl chloride, polyvinylidene chloride, etc.Also, aromatic resins containing bromine atoms, iodine atoms, etc. are being developed recently from the perspective of increasing the refractive index of resin lenses. Various resins can be mentioned, such as aromatic resins, resins containing sulfur atoms, phosphorus atoms, etc.

In the present invention, various polarizing films can be used. Specific examples include an iodine-volivinyl alcohol polarizing film called a so-called thin-film type polarizing film, a highly dichroic dye-polyvinyl alcohol polarizing film, and a film produced by intramolecular dehydration or dehydrochlorination of polyvinyl alcohol or polyvinyl chloride. Examples include so-called polyvinylene-based polarizing films that have a polyene structure and obtain polarizing properties through conjugated double bonds, and others.

Iodine-based polyvinyl alcohol polarizing films are mainly neutral or blue-based, and dye-based polyvinyl alcohol polarizing films are preferably used in the present invention, especially when coloring is intended. Further, in order to protect the polarizing film, a protective layer may be formed by laminating another transparent film such as a triacetate film on both surfaces or one surface of the polarizing film.

In the polarizing resin optical member of the present invention, in order to obtain a light control function, at least one or more spirooxazine compounds represented by the general formula (I) are contained in any part thereof. I am forced to do it.

Specific examples of such spirooxazine compounds include 1,3.3-}limethylspiro[indoline-2,3'
(3H)-pyrido(3.4-f)(I,4)penzoxazine] l-isoprobyl-3,3-dimethylspiro[indoline-2.3'-(3H)-pyrido(3.4-f) )
(I, 4) penzoxazine], 1-benzyl-3,3-dimethyl spout [indoline-2,3°-(3H)-pyrido (3.4-f) (
I, 4) penzoxazine), l-(2-phenoxyethyl)-3,3-dimethylspiro[indoline-2,3°-(3H) monopyrido(3,4
f) (I.4) Penzoxazine], 1-(p-
methoxybenzyl)-3,3-dimethylspiro [indoline-2,3°-(3H)-monopyrido(3,4f)
(I, 4) Penzoxazine], 1-(2-methoxyethyl) -3. 3-dimethylspiro [indoline-2.3” (3H) monopyrido (3.4-f) (I4> penzoxazine], 1,3-dimethyl-3-ethylspiro [indoline 2,
3” (3H) one pyrido (3, t- f ) (L 4
) penzoisazine], 5-chloro-1.3.3-}limethylspiku [intrin-2.3'-(3H)-pyrido (3.4-f)
(L4) penzoxazine], L3,35-tetramethylspiro[indoline-2.3
(3H)-pyrido(3.4-f) (I.4)penzoxazine], 2″-(N.N-diethylamino)-1 3 :3-
Trimethylspiro [indoline-2.3"-(3H)-1pyrido(3.4-f) (I.4) pensoxazine], 1-isopropyl-3-methyl-3-ethylspiro[indoline-2.3" -(3H)-pyrido(3
．． 4-f) <1.4) Penzoosazine], 1-phenethyl-33-dimethylspiro[indoline-23″-(3H)-pyrido(3.4-f) (I
, 4) Penzoxazine], 1-(2-ethoxyethyl)-3.3-dimethylspiro[Indoline-2.3'-(3H)-pyrido(3.4-
f) (I. 4) Penzoxazine], 5-chloro-1.3edimethyl-3-ethylspiro[indoline-2.3” (3H)-pit (3.4-f) (
L 4) Penzoxacin], 5-methoxy1.3,:3-}limethylspiro[indoline-2.3-(3}I)-pyrido(3..4
-f) (I. 4) Penzoxazine], ], 3, 3, 5. 6-pentamethyl spiro[indoline 2,3'-(3H)-pyrido (3.4-r
) (I. 4) Penzoisazine], 8-Hydroxy-1.3.3-}limethylspinal [Indoline-2,3''-(3H)-pyrido(3.4-
f) (I,4)penzoxazine], 8-methoxy1,3,3-trimethylspiro[indoline-2,3°-(3H)-pyrido(3.4-f)
(I, 4) penzoxazine], and others, but are not limited to these.

11 These spirooxazine compounds have excellent durability against repeated color development and fading due to irradiation and removal of light under normal environments, and also exhibit large color development even at room temperature or higher temperatures.

Among the spirooxazine compounds represented by the general formula (I), compounds in which R1 is a linear or branched alkyl group having 4 or more and 25 or less carbon atoms are particularly suitable for color-forming properties and repeated color-forming actions. Excellent durability.

Specific examples of such compounds include -(n-butyl)-3,3-dimethylspiro[indoline-2.3'-(3H)-pyrido(3.4-f)(
I. 4) Penzoxazine] I-isobutyl-3,3-dimethylspiro[indoline-2,3''-(3H)-pyrito(3,4-f) (
I. 4) Penzoxazine], 1-(n-amyl)-3,3-dimethylspiro[indoline-2.3'-(3H)-pyrido(3,4-f
) (I. 4) Penzoxazine], -12 1-isoamyl-3,3-dimethylspiro[Indoline-2,3''-(3H) -pyrido (3.4-f) (
I. 4) Penzoisazine], 1-(n-hexyl)-3,3-dimethylspiku [indoline-2.3°-(3H)-pyrido(3.4-f)(
I,4) penzoxazine], 1-(n-h7'thyl)-3,3-dimethylspiro[indoline-2,3'-(3H)-monopyrido(3.4-
f) (I,4)penzoxazine], ■-(n-hevicyl)-3-methyl-3-ethylspiro [indoline-2,3'-(3H) monopyrido(3,4
f) (I.4) Penzoxazine], 1-cyclohexyl-3,3-dimethylspiro[indoline-2.
3'-(3H)-pyrido(3.4-f)(I
, 4) Penzoxazine], 1-hexylmethyl-3,3-dimethylspiro[
Indoline-2.3” (3H)-pyrido (3.4-f)
(I.4>penzoxazine], 1-(n-octyl13,3.5-trimethylspiro[
Indoline-2.3゜-(3H)-pyrido(3.4-f
) (I. 4) Penzoxazine], 1-(2-ethylhexyl)-33-dimethylspiro[
Indoline-2.3″-(3H)-pyrido(3.4-f
) (I. 4) Penzoxazine], 1-(n-decyl)-3,3-dimethylspiro[indoline-2.3''-(3H)-pyrido(3,4-f
) (L 4) penzoxazine], 1-(n-dodecyl)-3.3.2°-trimethylspiro[indoline-2.3'-(3H) monopyrido (3.4
-f)(I,4)penzoxazine], 1-(n-dodecyl>-3-methyl-3-ethylspiro [indoline-2.3”-(3H) monopyrido(3,4
f) (I, 4)penzoxazine], 1-(n-
dodecyl)-3,3-dimethyl spout [indoline-2
,3”-(3H)-pyrido(3.4-f) (I
．． 4) Penzoxazine], 1-(n-octadecyl)-3,3-dimethylspiro[
Indoline-2,3°-(3H)-pyrido(3,4-f
) (I. 4) Penzoxazine], 1-(n-docosyl)-3,3-dimethylspiro[Indoline-2,3''-(3H)-monopyrido (3.4-f
) (I, 4) Penzoxazine], 1-(n-hexyl) -3. 3, 4. 5-tetramethylspiro[indoline-2,3°-(3H)-pyrido(3.4-f) (I.4>penzoxazine),
1-(n-hexyl)-3. 3. 5. 6-tetramethylspiro [indoline-2,3'-(3H)-pyrido(3,4f) (I.4) penzoxazine],
8'-hydroxy-1-(n-hexyl)-3,3-dimethylspiro [indoline-2,3''-(3H)-pyrido(3,4-f) (I.4) penzoxazine]
, and others, but are not limited to these.

Next, a description will be given of means for applying the above polarizing film and spiroosazine compound to the main body of a resin optical member.

A mode of providing the polarizing film on the resin optical member body is as follows: (a) As shown in FIG. (Ex) As shown in FIG. 2, the polarizing film P is attached to at least one surface of the optical member main body 13 using an adhesive; (C) The optical member main body 13 is bonded together by cast polymerization. 13, the polarizing film P is immersed in the material monomer and the monomer is polymerized, thereby embedding the polarizing film P in the optical member main body 13, as shown in FIG. , etc. As already mentioned, the polarizing film may have a protective layer formed on both surfaces or one surface thereof.

A means for applying the specific spirooxazine compound to obtain a light control function is a means for providing a light control layer made of a resin containing the spirooxazine compound on an optical member body provided with a polarizing film as described above. Alternatively, it is possible to utilize a method of containing the spirooxazine compound in either or both of the polarizing film and the optical member main body of the optical member main body provided with the polarizing film as described above.

In the case of the latter method, in order to incorporate the spirooxazine compound into the optical member main body, the optical member main body is brought into contact by, for example, immersing the spirooxazine compound in a solution of an organic solvent. The compound can be diffused into the body of the optical member. Further, it is also possible to obtain an optical member having a light control function by mixing a spirooxazine compound with a polymerizable monomer that is polymerized to form an optical member main body, and then performing cast polymerization.

In the case of such a method, the spirooxazine compound is added in an amount of 0.00% based on 100 parts by weight of the resin. 00
It is preferably added in an amount of 1 to 50 parts by weight.

In the case of applying the spirooxazine compound by the former method, that is, by providing a light control layer, the spirooxazine compound is dissolved in an organic solvent together with the resin material for the light control layer, and this solution is used to apply the spirooxazine compound by providing a light control layer. What is necessary is just to apply|coat to the surface of an optical member main body, and to harden it as needed. The type of resin material for the light control layer used here is not particularly limited, and various transparent resin materials can be used. Specific examples include polymethyl methacrylate, polystyrene, polyvinyl acetate,
Examples include thermoplastic resins such as ethylene-vinyl acetate copolymer, polycarbonate, polyvinyl chloride, and polyethylene terephthalate, and thermosetting resins such as cellulose resins, polyurethane resins, melamine resins, Epoquin resins, and phenolic resins.

Furthermore, silicone hard coating resins and photocrosslinkable polyfunctional acrylic resins, which are generally known as hard coating agents, can also be used.

In the case of such means, the spirooxazine compound is added in an amount of 0 to 100 parts by weight of these resins.
．． It is preferably added in a proportion of 0.01 to 50 parts by weight.

For example, as shown in FIG. 4, the light control layer is provided on the surface of one optical member element 11 or the other optical member element 12 of the optical member body having the polarizing film P in the manner shown in FIG. be able to. C indicates a light control layer. Or the fifth
As shown in the figure, it is also possible to provide a light control layer C between the two optical member elements 11 and 12 in a state where it is laminated with a polarizing film P. Furthermore, as shown in FIG. A laminate of a polarizing film P and a light control layer C may be provided on the surface of the optical member main body 13. In the structures shown in FIGS. 5 and 6, the order of the polarizing film P and the light control layer C is not particularly limited. That is, the light control layer can be provided alone in the same manner as the polarizing layer P shown in FIGS. 1 to 3 by bonding, pasting, embedding during cast polymerization, etc. .

As described above, the spirooxazine compound is contained in the optical member main body or light control layer made of resin to form a light control function part, but the resin of the light control function part is three-dimensionally crosslinked. It is preferable that it has a structure.

This is because, in a resin having a three-dimensional crosslinked structure, the spirooxazine compound can reliably exhibit an excellent dimming function over a long period of time even at 19 room temperature or higher temperatures.

Therefore, when providing a light control layer in the present invention, the resin material forming the light control layer may be a resin precursor forming a three-dimensionally crosslinked resin such as a thermosetting resin or a resin for a hard coating agent. Alternatively, a polyfunctional acrylic compound is used, the spirooxazine compound is mixed into this resin material to form a light control layer coating liquid, and this light control layer coating liquid is applied to the surface of an optical member body provided with a polarizing film. It is preferable to provide the light control layer on the surface of the polarizing film or the optical member main body by drying and shaping the film or further curing it.

In this case, the spirooxazine compound is preferably contained in a proportion of 0.01 to 50 parts by weight based on 100 parts by weight of the three-dimensional crosslinked resin, and the thickness of the light control layer is in the range of 1 to 100 tsubo. It is preferable that it be within.

If an independent light control layer is not formed, the main body of the optical part 20 or the polarizing film or its protective film may be formed with a resin having a three-dimensional crosslinked structure, or by immersing it in a solution of a spirooxazine compound. It is preferable to form the light control function portion by diffusing and incorporating a spirooxazine compound into the resin.

In this case, it is particularly preferable that the polarizing film is provided on the optical member main body in the manner shown in FIG.

In any of the above cases, in order to improve the weather resistance of the subirooxazine compound, antioxidants, ultraviolet absorbers that block unnecessary short wavelength light, and light stabilizers are added to the subirooxazine compound. It is also possible to add other additives.

In particular, by using a hindered amine light stabilizer as a light stabilizer in combination with the spirooxazine compound, it is possible to further improve the weather resistance of the resulting optical material having a dimming effect. Such light stabilizers include bis(I, 2, 2, 6. 6-pentamethyl-4
-piperidyl) sebacate, bis(2. 2, 6. 6-tetramethyl-4-piperidyl) sebacate, di(I, 2, 2, 6. 6-pencmethyl-4-
piperidyl)butyl (3'.5"-di-tert-butyl-4-hydroxybenzyl) malonate, 1- (2- [3-(3.5-di-tert-butyl-4-hydroxyphenyl) propionyloxy] ethyl} -4- (3-(3,5-di-tert-butyl-4
hydroxyphenyl)propionyloxy]2, 2,
6. 6-tetramethylpiveridine, poly { (
6-((I, 1.3.3-tetramethylbutyl)amino)-1.3.5-}riazine-2,4-diyl] [
1.6 - (2, 2, 6. 6-tetramethyl-
4-piperidinyl)aminehexamethylene]}, poly((6-(morpholino)-S-}riazine2,
4-diyl) [1,6-(2,2,6.6-tetramethyl4-piperidyl)amino]hexamethylene}, 4
-Hydroxy-2. 2, 6. 6-tetramethyl-
Dimethyl succinate polymers with 1-piperidinethanol and other commercially available products can be usefully used.

The light stabilizer is 0.01 to 50 parts by weight based on 100 parts by weight of the resin containing the spirooxazine compound,
It is preferably used in an amount of 0.01 to 30 parts by weight.

Furthermore, a singlet oxygen quencher can be added for the purpose of suppressing the adverse effect of oxygen on the coloring mechanism of the spirooxazine compound and improving the durability of the coloring action of the spirooxazine compound. Specific examples of such singlet oxygen quenchers include β-monocarotene, various ship base Ni(I[) complexes, 1,4-diazabicyclo[2,
2, 2) Amines such as octane and triethylamine, and the already mentioned phenols can be mentioned.

Among these, amines and phenols can be preferably used because they have no absorption in the visible region although the singlet oxygen extinction coefficient is somewhat small. The amount of the singlet oxygen quencher added is preferably as large as possible, but 0.1 parts by weight per 100 parts by weight of the resin containing the spirooxazine compound.
-10 (l parts by weight, preferably 0.5=23-50 parts by weight).

In the manner described above, it is possible to obtain a resin optical member having both a polarizing function and a light control function using an organic photochromic substance made of a specific spirooxazine compound.

This optical member can be suitably used as it is as a polarized lens, sunglasses, or goggles, but it can also be coated with a hard coat or non-reflective coating that is usually applied to polarized lenses, sunglasses, and goggles. It can also be dyed.

In particular, if the light control function part containing the spirooxazine compound is exposed on the outer surface, the spirooxazine compound may be hydrolyzed by atmospheric moisture, human sweat, etc. after a considerable period of time has passed. Therefore, it is preferable to provide, for example, a silicone-based hard coat layer on the surface. In this case, the thickness of the hard coat layer is preferably in the range of 0.1 to 200 μs.

-24 [Example] Examples of the present invention will be described below, but the present invention is not limited thereto.

In addition, the measurement of the light transmittance in each Example was performed using a light beam having a peak wavelength at which the change in the light transmittance was maximum.

Example 1 Commercially available polyvinyl alcohol-iodine complex polarizing film (neutral gray color, degree of polarization 94.5%, single transmittance 45.8%)
, parallel transmittance 39.6%, orthogonal transmittance 2.2%) was hot-pressed into a spherical lens shape, and held in a glass mold for lens production. A monomer mixture of 100 parts by weight of allyl carbonate and 2.5 parts by weight of isopropyl peroxydicarbonate as a polymerization initiator was injected, and the temperature was raised sequentially from 40°C to 80°C over 20 hours to polymerize. As a result, a polarizing resin lens made of diethylene glycol bisallyl carbonate having a polarizing film embedded therein was produced as shown in FIG.

On the other hand, 1. ．． 3.3-}Limethylspiro [indoline 2
,3″-(3H)pyrido(3, ,l-f)(I.
4) 4.0 parts by weight of penzoxazine] and 100 parts by weight of Epoquine resin precursor "Eponisox [100 Clear" (manufactured by Dainippon Paint Co., Ltd.)] were dissolved in 100 parts by weight of methyl ethyl ketone to prepare a light control layer. A coating solution was prepared. This light control layer coating solution was applied to the above-mentioned polarizing resin lens by dipping, dried at 40°C until the coated surface lost its tackiness, and then cured at 80°C for 16 hours to a thickness of 7.
A polarizing resin lens having a light control layer on the side was produced.

This lens had a slight green tinge, and when exposed to sunlight, it gradually changed from gray to blue-green. In addition, when this lens is irradiated with ultraviolet rays, it develops a color, and the change in transmittance of light with a peak wavelength of 612 nm is 42% before irradiation with ultraviolet rays, and 25% after 5 minutes of irradiation with ultraviolet rays. It declined to . Thereafter, when the film was placed in a dark place, the light transmittance returned to its original state.

Further, a commercially available silicone hard coat agent "Tosguard 520J (manufactured by Toshiba Silicone ■)" was applied to the surface of the light control layer of this lens by a dipping method, and then heated and cured to form a hard coat.

This lens was measured with a weather meter "Atlas Weatherometer C135" (manufactured by Toyo Seiki Seisakusho) at 120
After performing accelerated deterioration treatment by time treatment, and then UV irradiation in the same manner as above, the transmittance of light with a peak wavelength of 612 nm was measured, and it was 42% before UV irradiation, and the UV irradiation time was 5. 32 minutes have elapsed
%.

Example 2 26.97 parts by weight of 2-hydroxyethyl methacrylate and 23.9 parts by weight of inphorone diisocyanate. 03 parts by weight, 50 parts by weight of 2-ethyl hequinyl methacrylate, and 0.0 parts by weight of di-n-butyltin silaurate as a urethanization catalyst.
5 parts by weight was added, and the urethane-forming reaction was carried out at 60° C. for 3 hours.

The urethane monomer composition 27 thus obtained was added with 1,3.3-}'J methylspiro[indoline-2
3'-(3H)-pyrido(3 4-f ) (I, 4
) After adding and mixing 0.2 parts by weight of penzoxazine, 1.0 parts by weight of tert-butylperoxypiparate as a polymerization initiator was added to form a monomer composite solution having photochromic properties. I got it.

This monomer composition solution was poured into a glass mold holding a polarizing film in the same manner as in Example 1, and the temperature was raised sequentially from 40 to 80°C over 20 hours to polymerize. A polarizing resin lens was manufactured in which a polarizing film was embedded and the optical member body had a light control function.

This lens has a slightly green tint, and when it is irradiated with ultraviolet rays, it develops a color.The change in transmittance of light with a peak wavelength of 612 nm due to this is 40% before irradiation with ultraviolet rays, and when the irradiation time is 5 minutes. After that, the percentage changed to 14%. Thereafter, when the lens was placed in a dark place, the transmittance of the light beam returned to its original state.

This lens was subjected to accelerated deterioration treatment in the same manner as in Example 1, and then irradiated with ultraviolet rays in the same manner as above to measure the transmittance of light with a peak wavelength of 612 nm. %, and decreased to 19% when the ultraviolet irradiation time exceeded 5 minutes.

Example 3 A polarizing resin lens having an embedded polarizing film produced in the same manner as in Example 1 was treated with diethylene glycol 10
0 parts by weight and 1.3.3-1 methyl spiro[indoline-2,3°-(3H)-pyrido(3,4-f)(I.4
) Penzoxazine] was immersed in a mixed solution of 2.0 parts by weight at a temperature of 120° C. for IO minutes, thereby diffusing the spirooxazine compound to the surface portion of the lens.

After washing this lens with 2-propyl alcohol, the hard coat was removed in the same manner as in Example 1 to produce a polarizing resin lens having a light control function.

This lens had a slight green tinge, and when exposed to sunlight, it gradually changed from gray to blue-green. In addition, when this lens is irradiated with ultraviolet rays, it develops a color, and the change in transmittance of light with a peak wavelength of 612 nm is 43% before irradiation with ultraviolet rays, and decreases to 33% after 5 minutes of irradiation with ultraviolet rays. did. Thereafter, when the lens was placed in a dark place, the transmittance of the light beam returned to its original state.

Example 4 In the preparation of the monomer composition solution of Example 2, 1,3.3-}limethylspiro was used as the spirooxazine compound.
[Indoline-2,3'-(3H)-pyrido(3,4-
f) (I.4) 1-(n-hexyl)-3.3-dimethyl-indoline-2.3°-(3H)-pyrido(3.4-f) in place of 0.2 parts by weight of penzoxazine
) (I.4) penzoxazine) using 0.1 part by weight,
Bis(2, 2,
6. A polarizing film was embedded inside the optical member body in the same manner as in Example 2 except that 0.5 parts by weight of Sanol LS-7704 (manufactured by Sankyo ■) was added. We created a polarizing resin lens with a light control function.

This lens has a slightly green tint and develops color when it is irradiated with ultraviolet rays.The change in transmittance of light with a peak wavelength of 612 1m due to this is 38% before irradiation with ultraviolet rays, and the irradiation time is 5 minutes. After that, it dropped to 11%. After that, when I put the lens in a dark place,
The transmittance of the light beam returned to its original state.

This lens was subjected to accelerated deterioration treatment in the same manner as in Example 1, and then irradiated with ultraviolet rays to achieve a peak wavelength of 612 nm.
When the transmittance of light rays of m was measured, it was 38% before UV irradiation, and decreased to 14% after 5 minutes of UV irradiation. From this, it is clear that this lens has excellent weather resistance.

Example 5 1-isoamyl-3,3-dimethylspiro[indoline-2.3'-(3H)-pyrido(3.4-f)
(I, 4>penzoxazine)■. 0 parts by weight and 1- (2- (3-(
3.5-di-tert-butyl-4-hydroxyphenyl>probionyloxy]ethyl) -4- (3-(3
．． 5-di-tert-31 phthyl-4-hydroxyphenyl)probionyloxy) -2.2.6. 6-Tetramethylpiperidine “L
2.0 parts by weight of "S-2626" (manufactured by Sankyo ■) and 30 parts of ethylene vinyl acetate copolymer resin "Evaflex 150"
parts by weight were heated and dissolved in 300 parts by weight of toluene to prepare a light control film or solution, and this solution was cast on a Teflon sheet and dried to produce a light control film with a thickness of 20JIIn.

On each side of this light control film and a commercially available multicolor polarizing film (blue, transmittance 40%, polarization degree 91%),
Epoxy resin precursor “Epotec 301J (Epoxy resin)
(manufactured by Technology Co., Ltd.) and bonded the respective surfaces together, and then this was further coated with a layer of diethylene glycol bisallyl carbonate resin containing no ultraviolet absorber.
．． It is sandwiched between two 2mm resin lens elements and crimped.
Thereafter, by holding this at 80° C. for 3 hours, the polarizing resin according to the present invention has a structure shown in FIG. 5, in which a polarizing film and a light control film are laminated between two lens elements. A manufactured lens was manufactured.

32 Then, a hard coat layer was formed on both sides of this lens in the same manner as in Example 1.

This lens has a slightly greenish blue color, and when exposed to sunlight, the blue color gradually deepened.

In addition, when this lens is irradiated with ultraviolet rays, it develops a color, and the change in transmittance of light with a peak wavelength of 612 nm is 38% before irradiation with ultraviolet rays, and decreases to 15% after 5 minutes of irradiation with ultraviolet rays. did.

Thereafter, when the lens was placed in a dark place, the transmittance of the light beam returned to its original state.

Further, this lens was subjected to accelerated deterioration treatment in the same manner as in Example 1, and then irradiated with ultraviolet rays to obtain a peak wavelength of 6.
When the transmittance of 12 nm light was measured, it was 41% before UV irradiation, and decreased to 20% after 5 minutes of UV irradiation.

From this, it is clear that this lens has excellent weather resistance.

[Brief explanation of drawings]

FIGS. 1 to 3 are sectional views for explaining an embodiment in which a polarizing film is provided, and FIGS. 4 to 6 are sectional views for explaining an embodiment in which a light control layer is further provided. 11. 12... Optical member element 13... Optical member body P... Polarizing film C... Light control layer 35-

Claims (1)

[Claims] 1) A resin optical member main body and a polarizing film, and having a light control function portion containing at least one spirooxazine compound represented by the following general formula (I). An optical member made of polarizing resin that has a characteristic light control effect. General formula (I) ▲ Numerical formulas, chemical formulas, tables, etc. represents an aryloxyalkyl group, R^2 and R^3 each represent a substituted or unsubstituted alkyl group, R^4, R^5, R^
6 and R^7 each represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a hydroxyl group, an alkoxyalkyl group, or a substituted or unsubstituted amino group, and R^
4, R^6 and R^7 may each be plural. ) 2) The light control function portion is a light control layer made of a three-dimensional crosslinked resin containing the spirooxazine compound, and the light control layer is provided on the surface of a resin optical member body provided with a polarizing film. The polarizing resin optical member according to claim 1, characterized in that: 3) The polarized light according to claim 1, wherein the resin optical member main body is made of a three-dimensional crosslinked resin, and the spirooxazine compound is contained in the optical member main body to form a dimming function part. Optical components made of synthetic resin.