JPH057681B2 - - Google Patents

Description

[Detailed description of the invention]

[Industrial Field of Application] The present invention relates to a polarizing sheet having photochromic properties. [Prior Art] Products with various functions have been developed to make it easier to see objects and protect the eyes. Changes from colorless to colored. Much research has been carried out on so-called photochromic compounds and their applications. On the other hand, attempts have been made to use polarizing sheets to reduce glare caused by reflected light and to make the reflective surface itself easier to see. Many proposals have already been made regarding the use of such sheets having photochromic properties or sheets having a polarizing function alone. [Problems to be Solved by the Invention] However, there is no known sheet that satisfies both functions at the same time, and an object of the present invention is to provide a single sheet that has both functions. [Means for Solving the Problems] The present invention has the following configuration to achieve the above object. "At least a part of the substrate having a polarizing function,
1. A polarizing sheet having photochromic properties, comprising a film having a thickness of 0.1 to 30 μm and containing a singlet oxygen quencher. ” Here, a substrate with a polarization function is used to convert electromagnetic waves that vibrate perpendicularly to the direction of propagation of light, generally called natural light, which is a collection of light from vibration planes in all directions, into light that has a certain vibration bias. It is a substrate that has a function that allows for polarization, and its types include linear polarizing plates, circular polarizing plates, and elliptically polarizing plates. Especially for removing reflected light, such as water surfaces,
A linear polarizing plate is preferably used for the purpose of removing unpleasant glare reflected from glass surfaces, road surfaces, etc., and the photochromic coating of the present invention is particularly preferred since it controls the amount of light. Further, as a specific example of the substrate having the polarizing function, a film made by stretching polyvinyl alcohol and then adsorbing iodine is a preferable polarizing substrate because it is inexpensive and easily available. It is not particularly limited as long as it has the following. On the other hand, such polarizing films also have heat resistance,
In order to provide sufficient water resistance, chemical resistance, light resistance, etc., it is generally preferable to use a composite of various substrates in the form of a sandwich. Inorganic glass and various plastics, especially plastics that do not have birefringence, are preferably used as the substrate used for the sandwich. Among such plastics, acrylic plates, thermoplastic resins such as acetyl cellulose, and thermosetting resins such as diethylene glycol bisallyl carbonate polymer plates are particularly preferably used from the viewpoint of moldability and flexibility. In the case of linear polarization, the polarization function is as follows ()
Those having a degree of polarization expressed by the formula of 70% or more are preferably used from the viewpoint of polarization performance. V (%)=Fp/F×100 () Here, V is the degree of polarization, F is the polarized light flux, and Fp is the light flux for vibration in either the vertical or horizontal direction. The present invention provides a film having a photochromic property on at least a portion of the substrate having a polarizing function, which has a thickness of 0.1 to
Although the film is provided with a 30 μm coating, not only various known photochromic compounds but also other photochromic compounds can be used to impart photochromic properties. For specific examples of such photochromic compounds, see, for example, GH
BROWN, “PHOTOCHROMISM”, Wiley
Interscience, New York (1971)
Publication No. 28892, Japanese Patent Publication No. 49-48631, Japanese Unexamined Patent Publication No. 1983
-36284 Publication, JP-A-61-53288, JP-A-Sho
61-161286, JP 61-161287, JP 61-233079, JP 61-243087, JP 61-268686, JP 62-33184
Publication No. 153288, Japanese Patent Publication No. 153288, Japanese Patent Publication No. 1982-15328-
Examples are given in Publication No. 164685. In particular, a photochromic compound represented by the following general formula (A) is particularly preferably used from the viewpoint of color developing/fading property, repeatability, etc. (However, X is C-R ₉ or nitrogen, and R ₉
is hydrogen, _C1 - _C8 alkyl group, alkoxy group,
Selected from halogen. R ₁ is selected from the group consisting of a C ₁ to C ₆ alkyl group and a C ₇ to _{C 20} substituted or unsubstituted aralkyl group. R ₂ and R ₃ are each hydrogen, a C ₁ to _{C 5} alkyl group, a phenyl group,
selected from the group consisting of mono- or di-substituted phenyl group, benzyl group, or combined with 6 to
It is selected from a cyclic ring selected from an alicyclic ring containing 8 carbon atoms (including spiro carbon atoms), a norbornyl group, and an atamantyl group. R ₄ , R ₅ , R ₆ , R ₇ and R ₈ are each hydrogen, C ₁ to C ₅ alkyl group, alkoxy group, halogen, nitro group, cyano group, hydroxy group, C ₁ to _{C 5} halogen selected from alkyl groups, alkoxycarbonyl groups, and amino groups. ) Specific examples of such spirooxazine compounds include 1-benzyl-3,3-dimethylspiro[indolino-2,3'-[3H]naphtho[2,1-b]
(1,4)oxazine], 1-(4-methoxybenzyl)-3,3-dimethylspiro[indolino-
2,3′-[3H]naphtho[2,1-b](1,4)
oxazine], 1-(2-methylbenzyl)-3,
3-dimethylspiro[indolino-2,3'-
[3H]naphtho[2,1-b](1,4)oxazine], 1-(3-methylbenzyl)-3,3-dimethylspiro[indolino-2,3'-[3H]naphtho[2,1 -b](1,4)oxazine], 1-(4-
methylbenzyl)-3,3-dimethylspiro[indolino-2,3'-[3H]naphtho[2,1-b]
(1,4)oxazine], 1-(3,5-dimethylbenzyl)-3,3-dimethylspiro[indolino-2,3'-[3H]naphtho[2,1-b](1,
4) Oxazine], 1-(2,4,6-trimethylbenzyl)-3,3-dimethylspiro[indolino-2,3'-[3H]naphtho[2,1-b](1,
4) Oxazine], 1-(4-chlorobenzyl)-
3,3-dimethylspiro[indolino-2,3'-
[3H]naphtho[2,1-b](1,4)oxazine], 1-(4-bromobenzyl)-3,3-dimethylspiro[indolino-2,3'-[3H]naphtho[2,1 -b](1,4)oxazine], 1-(2-
fluorobenzyl)-3,3-dimethylspiro[indolino-2,3'-[3H]naphtho[2,1-
b](1,4)oxazine], 1-(3-fluorobenzyl)-3,3-dimethylspiro[indolino-2,3'-[3H]naphtho[2,1-b](1,
4) Oxazine], 1-(4-fluorobenzyl)
-3,3-dimethylspiro[indolino-2,
3′-[3H]naphtho[2,1-b](1,4)oxazine], 1-(2,4-difluorobenzyl)-
3,3-dimethylspiro[indolino-2,3'-
[3H]naphtho[2,1-b](1,4)oxazine], 1-(2,3,4,5,6-pentafluorobenzyl)-3,3-dimethylspiro[indolino-2,3' −[3H]naphtho[2,1-b](1,
4) Oxazine], 1-(4-cyanobenzyl)-
3,3-dimethylspiro[indolino-2,3'-
[3H]naphtho[2,1-b](1,4)oxazine], 1-(4-trifluoromethylbenzyl)-
3,3-dimethylspiro[indolino-2,3'-
[3H]naphtho[2,1-b](1,4)oxazine], 1-(4-nitrobenzyl)-3,3-dimethylspiro[indolino-2,3'-[3H]naphtho[2,1 -b](1,4)oxazine], 1-(2-
phenylethyl)-3,3-dimethylspiro[indolino-2,3'-[3H]naphtho[2,1-b]
(1,4)oxazine], 1-(3-phenylpropyl)-3,3-dimethylspiro[indolino-
2,3′-[3H]naphtho[2,1-b](1,4)
oxazine], 1-(2-naphthyl)-3,3-dimethylspiro[indolino-2,3'-[3H]naphtho[2,1-b](1,4)oxazine], 1,
3,3-trimethylspiro[indolino-2,
3′-[3H]naphtho[2,1-b](1,4)oxazine, 1,3,3-trimethylspiro[indolino-2,3′-[3H]pyrido[2,1-b](1 ，
4) benzoxazine]. Furthermore, these photochromic compounds can be used not only alone, but also in combination of two or more. These photochromic compounds are used by being dispersed in an organic polymer matrix, but the organic polymer is not particularly limited as long as it has good compatibility with the photochromic compound. Specific examples of organic polymers that can be used include acrylic resins, polyurethane resins, epoxy resins, melamine resins, polyvinyl acetate, polycarbonates, polystyrene resins, and celluloses such as cellulose acetate, cellulose acetate butyrate, hydroxyethyl cellulose, and hydroxypropyl. cellulose, and even polyvinyl alcohol,
Examples include urea resin and nylon resin. In addition, two or more of these resins can be used in combination, and various curing agents, crosslinking agents, etc. can be added to achieve three-dimensional crosslinking. In particular, matrices made by crosslinking acrylic resins with hydroxyl or carboxyl groups in their side chains with melamine resins, and matrices made by crosslinking acrylic resins with amino groups with epoxy resins as organic polymers are particularly useful for photochromics. The repetition resistance of the compound, the rate of color development and fading, and when a hard coat layer is provided on the coating, the resistance to solvents when coating the hard coat layer,
This is particularly preferred from the viewpoint of adhesion to the hard coat film. Furthermore, a radically polymerizable functional group such as a methacrylic group, an acrylic group, a vinyl group, a methacryloxy group, an acryloxy group, a methacryloxyalkyl group, or an acryloxyalkyl group is introduced as a substituent into the photochromic compound described above. However, it is also possible to contain it pendantly in an organic polymer. Introducing such a photochromic compound into an organic polymer through chemical bonding improves the dissolution properties of the photochromic compound,
It is useful because it allows control of light fastness and rate of color development and fading. In addition, the film thickness of the film having photochromic properties in the present invention is determined from the viewpoint of color density after irradiation with light and prevention of uneven color density due to film thickness.
It is necessary that it is 0.1μm or more, preferably
It is desirable that the thickness is 2 μm or more. Further, from the viewpoint of ease of application and uniformity, it is necessary that the thickness is 30 μm or less, and preferably 25 μm or less. The amount of the photochromic compound contained in the photochromic coating should be determined based on the required performance, especially the relationship with the coloring density, but when using the sheet of the present invention for optical lenses such as ski sunglass lenses, it is recommended to 20 weight percent is preferred. More preferably, it is 0.5 to 15 weight percent. If the amount is less than 0.1% by weight, the color density at room temperature will be poor. Moreover, if it exceeds 20% by weight, it becomes necessary to increase the amount of solvent relative to the matrix resin due to solubility.
It becomes difficult to obtain a sufficient coating thickness. The coating of the present invention can be applied to a substrate by applying a coating composition made of a mixed solution of the matrix resin and a photochromic compound by dipping or spin coating, or by coating the substrate with the matrix resin in advance. Various methods can be applied, such as a method in which the photochromic compound is incorporated into the matrix resin by using a dyeing method or the like after being coated on the matrix resin. Various organic solvents can be used as the solvent when applied as a coating composition, specifically various alcohols, ketones, ethers, esters, aromatic (halogenated) hydrocarbons, There are no particular limitations on the material as long as it dissolves both the matrix resin and the photochromic compound, such as aliphatic (halogenated) hydrocarbons, cellosolves, various formamides, and sulfoxides. In the present invention, it is preferable to further coat the above-mentioned film with a film having hard coat properties, and the film is preferably a polyorganosiloxane having hard coat properties. Here, the polyorganosiloxane having hard coat properties is not particularly limited as long as it can improve the scratch resistance of the film having photochromic properties and is crosslinked, but it has good adhesion to the film, low temperature, short time curing. Since it is possible, the following general formula
A cured polyorganosiloxane film obtained from the organosilicon compound represented by (b) and/or its hydrolyzate is preferably used. R ¹² _a R ¹³ _b SiY _4-ab (b) (Here, R ¹² and R ¹³ are each an alkyl group, an alkenyl group, an aryl group, or a halogen, a glycidoxy group, an epoxy group, an amino group, a mercapto group, a (meth) ) a hydrocarbon group having an acryloxy group or a cyano group, Y is a hydrolyzable group,
a and b are 0 or 1). Specific representative examples of the organosilicon compound represented by general formula (b) and/or its hydrolyzate include methyl silicate, ethyl silicate, n-
Propyl silicate, i-propyl silicate,
Tetraalkoxysilanes such as n-butylsilicate, sec-butylsilicate and t-butylsilicate, and their hydrolysates, as well as methyltrimethoxysilane, methyltriethoxysilane, methyltrimethoxyethoxysilane, methyltriacetoxysilane, methyl Tributoxysilane, ethyltrimethoxylane, ethyltriethoxysilane, vinyltrimethoxysilane, vinyltriethoxysilane, vinyltriacetoxysilane, vinyltrimethoxyethoxysilane, phenyltrimethoxysilane, phenyltriethoxysilane, phenyltrimethoxysilane Acetoxysilane, γ-chloropropyltrimethoxysilane, γ-chloropropyltriethoxysilane, γ-chloropropyltriacetoxysilane, 3,3,3-trifluoropropyltrimethoxysilane, γ-methacryloxypropyltrimethoxysilane, γ -aminopropyltrimethoxysilane, γ-aminopropyltriethoxysilane, γ-mercaptopropyltrimethoxysilane, γ-mercaptopropyltriethoxysilane, N-β-(aminoethyl)-γ-aminopropyltrimethoxysilane, β- Cyanoethyltriethoxysilane, methyltriphenoxysilane, chloromethyltrimethoxysilane, chloromethyltriethoxysilane, glycidoxymethyltrimethoxysilane, glycidoxymethyltriethoxysilane, α-glycidoxyethyltrimethoxysilane, α -glycidoxyethyltriethoxysilane, β-glycidoxyethyltrimethoxysilane, β-glycidoxyethyltriethoxysilane, α-glycidoxypropyltrimethoxysilane, α-glycidoxypropyltriethoxysilane, β -Glycidoxypropyltrimethoxysilane, β-glycidoxypropyltriethoxysilane, γ-glycidoxypropyltrimethoxysilane, γ-glycidoxypropyltriethoxysilane, γ-glycidoxypropyltripropoxysilane, γ -Glycidoxypropyltributoxysilane, γ-glycidoxypropyltrimethoxyethoxysilane, γ-glycidoxypropyltriphenoxysilane, α-glycidoxybutyltrimethoxysilane, α-glycidoxybutyltriethoxysilane , β-glycidoxybutyltrimethoxysilane, β-glycidoxybutyltriethoxysilane, γ-glycidoxybutyltrimethoxysilane, γ-glycidoxybutyltriethoxysilane, δ-glycidoxybutyltrimethoxysilane , δ-glycidoxybutyltriethoxysilane, (3,4-epoxycyclohexyl)methyltrimethoxysilane, (3,4-epoxycyclohexyl)methyltriethoxysilane, β-(3,
4-epoxycyclohexyl)ethyltrimethoxysilane, β-(3,4-ethylcyclohexyl)
Ethyltriethoxysilane, β-(3,4-epoxycyclohexyl)ethyltripropoxysilane, β-(3,4-epoxycyclohexyl)ethyltributoxysilane, β-(3,4-epoxycyclohexyl)ethyltrimethethoxyethoxy Ran, β-(3,4-epoxycyclohexyl)ethyltriphenoxysilane, γ-(3,4
-epoxycyclohexyl)propyltrimethoxysilane, γ-(3,4-epoxycyclohexyl)propyltriethoxysilane, δ-(3,4-epoxycyclohexyl)propyltriethoxysilane,
-epoxycyclohexyl)butyltrimethoxysilane, δ-(3,4-epoxycyclohexyl)
Trialkoxysilanes such as butyltriethoxysilane, triacyloxysilanes or triphenoxysilanes or their hydrolysates, dimethyldimethoxysilane, phenylmethyldimethoxysilane, dimethyldiethoxysilane, phenylmethyldiethoxysilane, γ-chloro Propylmethyldimethoxysilane, γ-chloropropylmethyldiethoxysilane, dimethyldiacetoxysilane, γ-methacryloxypropylmethyldimethoxysilane, γ-methacryloxypropylmethyldiethoxysilane, γ-mercaptopropylmethyldimethoxysilane, γ-mercaptopropyl Methyldiethoxysilane, γ-aminopropylmethyldimethoxysilane, γ-aminopropylmethylethoxysilane, methylvinyldimethoxysilane, methylvinyldiethoxysilane, glycidoxymethylmethyldimethoxysilane, glycidoxymethylmethyldiethoxysilane, α -Glycidoxyethylmethyldimethoxysilane, α-glycidoxyethylmethyldiethoxysilane, β-glycidoxyethylmethyldimethoxysilane, β-glycidoxyethylmethyldiethoxysilane, α-glycidoxypropylmethyldimethoxysilane ,α
-Glycidoxypropylmethyldiethoxysilane, β-glycidoxypropylmethyldimethoxysilane, β-glycidoxypropylmethyldiethoxysilane, γ-glycidoxypropylmethyldimethoxysilane, γ-glycidoxypropylmethyldiethoxy Silane, γ-glycidoxypropylmethyldipropoxysilane, γ-glycidoxypropylmethyldibutoxysilane, γ-glycidoxypropylmethyldimethoxyethoxysilane, γ
-Glycidoxypropylmethyldiphenoxysilane, γ-glycidoxypropylethyldimethoxysilane, γ-glycidoxypropylethyldiethoxysilane, γ-glycidoxypropylethyldipropoxysilane, γ-glycidoxypropylvinyl Dialkoxysilanes, diphenoxysilanes or diacyloxysilanes such as dimethoxysilane, γ-glycidoxypropylvinyldiethoxysilane, γ-glycidoxypropylphenyldimethoxysilane, γ-glycidoxypropylphenyldiethoxysilane An example is a hydrolyzate or a hydrolyzate thereof. It is also possible to add one type or two or more types of these organosilicon compounds. It is preferable to use such an organosilicon compound by hydrolyzing it in terms of low temperature curing and shortening of curing time. For hydrolysis, normal hydrolysis methods can be applied, such as pure water, hydrochloric acid, sulfuric acid,
Acidic aqueous solution such as acetic acid, or caustic soda,
This is done by adding an alkaline aqueous solution such as caustic potash or calcium hydroxide. The temperature during hydrolysis is not particularly limited, and there is no problem in controlling it to either a low temperature or a high temperature depending on the purpose. Curing of organosilicon compounds and/or their hydrolysates is usually carried out by heating, but various curing catalysts are added for the purpose of shortening heating time and curing at low temperatures. Examples of the curing catalyst include alkali metal salts of carboxylic acids and chelate compounds of aluminum, titanium, zirconium, and the like. In particular, aluminum chelate compounds such as acetylacetone aluminum salt are preferably used from the viewpoint of composition stability, transparency, and absence of coloration. Among the organosilicon compounds represented by (b) above, R ¹² and R ¹³ are preferred from the viewpoint of adhesion to photochromic coatings, improvement in surface hardness, heat resistance, weather resistance, etc.
Preferred examples include an alkyl group having 1 to 4 carbon atoms, an alkenyl group, or a phenyl group, as well as an organic group having an epoxy group or a glycidoxy group. The thickness of the polysiloxane coating applied to the present invention is sufficient as long as it prevents the photochromic coating from becoming easily damaged, and should be determined in relation to the photochromic coating.
From the standpoint of protecting the film, the thickness is 0.2 μm or more, preferably 0.5 μm or more. In addition, from the viewpoint of preventing cracks caused by bending during processing, etc., we recommend
Preferably it is 30 μm or less. Such film thickness is usually controlled by diluting with a solvent, but it can also be controlled by coating conditions.
The solvent that can be used is not particularly limited as long as it can uniformly dissolve the composition, but water, lower alcohols, etc. are preferably used in order to prevent elution and decomposition of the photochromic compound contained in the coating. It will be done. These solvents can be used as a mixed solvent of two or more. In the present invention, it is possible to pre-treat the photochromic coating in advance for the purpose of improving the adhesion with the photochromic coating when applying the polysiloxane coating. Examples of pretreatment methods include activated gas treatment, particularly low-temperature plasma treatment, in order to prevent decomposition of the photochromic compound in the photochromic coating and significantly improve adhesion. The type of gas used for the activated gas treatment should be appropriately selected depending on the type of organic polymer in the photochromic coating, but it is generally preferable to use oxygen gas. The polarizing sheet made of the photochromic film and polysiloxane film formed as described above has sufficient photochromic properties in addition to the polarizing function, and the surface is resistant to scratches.
Although there are no practical problems, in order to further improve the durability, especially the fatigue resistance of the photochromic coating, we add the following to the photochromic coating and, if necessary, to the polysiloxane coating:
Add singlet oxygen quencher. Many known compounds can be used as singlet oxygen quenchers, but N _i salt compounds and/or hindered amine compounds are particularly effective for spirooxazine compounds, which are photochromic compounds represented by general formula (A). can be mentioned.
In particular, a chelate compound of _Ni such as acetylacetone nickel salt is preferably used from the viewpoint of stability of the coating composition used for preparing a photochromic film. The amount of these singlet oxygen quenchers to be added is optimized depending on the conditions of use and the environment, but from the viewpoint of the effect of addition and the coloring of the photochromic film, it is usually expressed by the general formula (A). It is used in an amount of 1 to 200 parts by weight per 100 parts by weight of the photochromic compound contained in the photochromic coating. Furthermore, it is also possible to add ultraviolet absorbers, antioxidants, dyes, etc. to the photochromic coating and polysiloxane coating, respectively, as required. In a preferred embodiment of the present invention, a coating composition that forms a photochromic film and a polysiloxane film is applied to a polarizing plate made of plastic or colored plastic, so that it has photochromic properties and hard coat properties in addition to the polarizing function. One example is a method of assigning. When performing such coating, it is effective to add various surfactants, such as silicone surfactants and fluorine surfactants, for the purpose of improving the uniformity and smoothness of the coating. In addition, since the obtained polarizing sheet has flexibility, it can be bent and processed, so it is also preferable to make it into single-lens lenses, such as for goggles, at low cost by punching and heat bending. This is an embodiment. Furthermore, when used in goggles, it is also useful to apply an anti-fog finish to the inner surface. [Examples] Examples are shown below, but the present invention is not limited to these examples. Example 1 (1) Preparation of photochromic coating (a) Preparation of coating composition A copolymer (OH
3000 g of a 50% by weight solution of toluene/butyl acetate (50/50 weight ratio) of 10) was further diluted to 25% by weight with methyl ethyl ketone, a silicone surfactant was added, and 1-( 3-methylbenzyl)-3,3-dimethylspiro[indolino-2,3'-[3H]naphtho[2,1-b](1,4)-oxazine] at 150.0
g and 90.0 g of hindered amine were added,
The mixture was thoroughly stirred and dissolved to obtain a coating composition. (b) Application and drying The coating composition obtained in (a) above was applied to a plastic polarizing plate (manufactured by Sanritsu Electric Co., Ltd., HC ₂
-4-75 type, thickness 0.75 mm, 310 x 87 (mm) was coated using the dip method at a pulling speed of 20 cm/min. The coated sheet was dried at 65℃ for 4 hours.
Hardening was performed. (2) Performance test The following tests were conducted. The results are shown in Table 1. (B) Adhesion test As a test method, a steel knife is used to make 1 mm square gongs on the coating surface of the sheet that reach the substrate.
Put the pieces in and firmly stick them with cellophane adhesive tape (product name: “Cellotape” manufactured by Nichiban Co., Ltd.).
It was rapidly peeled off in a 90 degree direction and the presence or absence of paint film peeling was examined. (b) Photochromic performance After light was irradiated using a chemical lamp as an excitation light source to develop color, the irradiation was stopped and the state of color development and rate of decolorization at that time were observed with the naked eye. All showed uniform color development. (c) Durability test The state of color development in photochromic performance after irradiation was observed using a fade meter manufactured by Suga Test Instruments Co., Ltd. for 40 hours. Example 2 On top of the plastic polarizing plate having the photochromic coating obtained in Example 1, a polysiloxane coating was further applied. (1) Preparation of polysiloxane coating (l) Preparation of coating composition In a reactor equipped with a rotor, 240 g of γ-glycidoxypropyltrimethoxysilane and 240 g of γ-glycidoxypropylmethyldiethoxysilane were added. 1470 g of vinyltriethoxysilane was charged, and while stirring using a magnetic stirrer, 510 g of a 0.05 N hydrochloric acid aqueous solution was added dropwise while maintaining the liquid temperature at 10°C. After the dropwise addition was completed, stirring was continued for an additional 30 minutes to perform hydrolysis. Summer. 56.0 g of acetylacetone aluminum salt was added as a curing agent to the obtained hydrolyzate, and ethanol/water (80/20 weight ratio) was added as an additional solvent.
Added 710.0g, silicone surfactant 6.0g
After adding and stirring thoroughly, a coating composition was obtained. (b) Coating and drying The paint obtained in the previous section (1) and (a) was applied to the polarizing plate having the photochromic film obtained in Example 1 and (1) using a dip method at a rate of 10 cm/min. The coating was applied by drying and curing at 65°C for 15 hours. (2) Performance test The same test as in Example 1 was conducted. Table 1 shows the results.
Shown below. Furthermore, the following tests were conducted. (a) Friction resistance test Using #0000 steel wool, the material was rubbed under a load of 200 g/cm ² to examine its resistance to scratches. As a result, there was no damage at all. (b) Heat resistance, moist heat resistance test Heat resistance: After being left in a hot air oven at 80°C for 2 hours, changes in appearance, adhesion, and photochromic properties were examined. Humidity and heat resistance: Changes in appearance, adhesion, and photochromic properties were examined after being left in high humidity at 40°C and 90% RH for one week. As a result, it was found that it had very excellent performance in both heat resistance and moist heat resistance. (c) Punching test A goggle-shaped single-lens lens was punched using a press machine, and a curved surface was further processed using a wooden mold. The appearance after processing was examined, especially the presence or absence of cracks and wrinkles on the surface. As a result, there was no change at all before and after the test, and neither cracks nor wrinkles were observed.

[Table] Application Example The polarizing sheet having photochromic properties obtained in Example 2 was cut into the shape of a single-lens lens by press processing. Thereafter, a curved surface was processed using heat bending, and the material was attached to a goggle frame. When I wore the created goggles and stood on the slopes of a ski resort and looked at the gap, I was able to clearly recognize the shape of the gap and was able to ski safely. This effect is due to the polarization and photochromic functions of the goggles of the present invention. [Effects of the Invention] The polarizing sheet having photochromic properties obtained by the present invention has the following effects. 1. It has both photochromic properties with excellent color developing and erasing properties and polarizing function. 2. Has photochromic properties with excellent repeatability. 3. It is a composite material with high surface hardness and excellent practical durability. 4. Composite with excellent heat resistance, water resistance, and acid resistance. 5. Color development after light irradiation can be freely selected from a wide range.

Claims (1)

[Claims] 1. At least a part of the substrate having a polarizing function,
1. A polarizing sheet having photochromic properties, comprising a film having a thickness of 0.1 to 30 μm and containing a singlet oxygen quencher. 2. A polarizing sheet having photochromic properties as set forth in claim 1, wherein the substrate having a polarizing function is an organic plastic. 3. A polarizing sheet having photochromic properties according to claim 1, wherein the coating is an organic polymer containing a spirooxazine compound represented by the following general formula (a). (However, X is C-R ₉ or nitrogen, and R ₉
is hydrogen, _C1 - _C8 alkyl group, alkoxy group,
Selected from halogen. R ₁ is selected from the group consisting of a C ₁ to C ₆ alkyl group and a C ₇ to _{C 20} substituted or unsubstituted aralkyl group. R ₂ and R ₃ are each hydrogen, a C ₁ to _{C 5} alkyl group, a phenyl group,
selected from the group consisting of mono- or di-substituted phenyl group, benzyl group, or combined with 6 to
It is selected from a cyclic ring selected from an alicyclic ring containing 8 carbon atoms (including spiro carbon atoms), a norbornyl group, and an adamantyl group. R ₄ , R ₅ , R ₆ , R ₇ and R ₈ are each hydrogen, C ₁ to C ₅ alkyl group, alkoxy group, halogen, nitro group, cyano group, hydroxy group, C ₁ to _{C 5} halogen selected from alkyl groups, alkoxycarbonyl groups, and amino groups. ) 4. The polarizing sheet having photochromic properties according to claim 1, wherein the singlet oxygen quencher is a Ni salt compound. 5. The polarizing sheet having photochromic properties according to claim 1, wherein the singlet oxygen quencher is a hindered amine compound. 6. A polarizing sheet having photochromic properties according to claim 1, wherein the polarizing sheet is a lens. 7. A polarizing sheet having photochromic properties according to claim 1, wherein the polarizing sheet is a single-lens lens.