TW201326322A - Antifogging plastic lens - Google Patents

Abstract

To provide an antifogging plastic lens exhibiting excellent anti-fog performance, which has excellent water resistance so that separation from a plastic lens does not easily occur even in cases where the antifogging plastic lens is in contact with water. An antifogging plastic lens which is obtained by forming a coating film that is formed of an antifogging agent on the surface of a plastic lens. This antifogging plastic lens is characterized in that the coating film is formed of an antifogging agent that contains a (meth)acrylic polymer having a repeating unit represented by formula (I) (wherein R1 represents a hydrogen atom or a methyl group, and R2 represents a hydrophilic group) and having an alkoxysilyl group represented by formula (II) (wherein each of R3, R4 and R5 independently represents an alkyl group having 1-4 carbon atoms or an alkoxy group having 1-4 carbon atoms, with at least one of R3, R4 or R5 being an alkoxy group having 1-4 carbon atoms; and R6 represents an alkylene group having 1-12 carbon atoms) at at least one end.

Description

Anti-fog plastic lens

The present invention relates to an anti-fog plastic lens. More specifically, the present invention relates to an antifogging plastic lens which is preferably used as an optical lens such as a spectacle lens for vision correction, an eyeglass lens for sunglasses, a lens for a goggle, or a lens for an optical device.

The surface characteristics required for plastic lenses used for glasses and the like are antifogging properties. The antifogging property is generally applied by applying a surfactant to a plastic lens (for example, refer to JP-A-2002-16185 and JP-A-2003-238207). However, when the surfactant is applied to the plastic lens, the formed coating film of the surfactant may have poor water resistance due to dissolution of the water when it adheres to the plastic lens, and the antifogging cannot be stably maintained. Sex.

In addition to an antifogging agent containing a surfactant, an antifogging agent and a coating composition having hygroscopicity are known for use as an antifogging agent for imparting antifogging property to a plastic lens (for example, refer to JP-A-2011-179007) Japanese Laid-Open Patent Publication No. 2000-44879, and an anti-fogging agent containing a photocatalyst such as titanium oxide (for example, refer to JP-A-2004-137350). As a plastic lens having antifogging property, a plastic lens having a surface layer containing a photocatalyst is known (for example, refer to Japanese Laid-Open Patent Publication No. 2004-109388).

However, the hygroscopic antifogging agent and the coating composition have the disadvantage that the strength of the formed coating film is lowered due to moisture absorption. Moreover, containing photocatalyst The surface layer may be deteriorated due to the catalytic action of the photocatalyst, or the transparency may be lowered.

The present invention has been made in view of the above-described conventional techniques, and an object thereof is to provide an antifogging plastic lens which is excellent in water resistance and antifogging property, and which is less likely to cause a decrease in antifogging property even when it comes into contact with water. Another object of the present invention is to provide an anti-fog plastic lens which has excellent anti-reflection properties and excellent anti-reflection properties when it forms an anti-reflection layer on the surface of the lens, and has excellent water resistance and excellent anti-fog property.

The present invention relates to:

[1] An antifogging plastic lens in which a coating film composed of an antifogging agent is formed on a surface of a plastic lens, characterized in that the coating film is antifogging containing a (meth)acrylic polymer. Forming the agent, the (meth)acrylic polymer having a repeating unit represented by the formula (I) and having an alkoxythio group represented by the formula (II) at at least one terminal:

(wherein R ¹ represents a hydrogen atom or a methyl group, and R ² represents a hydrophilic group)

(wherein R ³ , R ⁴ and R ⁵ each independently represent an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and at least one of R ³ , R ⁴ and R ⁵ is represented by An alkoxy group having 1 to 4 carbon atoms, and R ^{6 is} an alkylene group having 1 to 12 carbon atoms.

[2] The antifogging plastic lens according to [1], wherein, in the formula (I), R ² represents a hydrophilic group of the formula (III), a group represented by the formula (IV), a hydrogen atom, and At least one hydroxyl group having 1 to 4 carbon atoms, a terminal having a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and having a carbon number of 1 to 20, having a hydrogen atom or a carbon number at one end a polypropylene glycol having 1 to 10 carbon atoms of 1 to 10:

(wherein R ⁷ and R ⁸ each independently represent an alkylene group having 1 to 4 carbon atoms, and R ⁹ and R ¹⁰ each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms)

(wherein R ¹¹ represents an alkylene group having 1 to 4 carbon atoms, and R ¹² and R ¹³ each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, R ¹⁴ represents an organic group, and X ^- represents an anion).

[3] The antifogging plastic lens according to [1] or [2], wherein the number of the repeating units represented by the formula (I) is from 1 to 1,000.

[4] The antifogging plastic lens according to any one of [1] to [3], wherein an antireflection film is formed on a surface of the plastic lens, and a coating composed of an antifogging agent is formed on the antireflection film. Made of film.

The antifogging plastic lens of the present invention exhibits the following effects: it is excellent in water resistance, and is not easily detached from the plastic lens even when it comes into contact with water, and is excellent in antifogging property. Further, the antifogging plastic lens of the present invention can exhibit the following excellent effects when an antireflection layer is formed on the surface of the lens: it exhibits excellent anti-reflection properties and exhibits excellent water resistance and Anti-fog.

As described above, the antifogging plastic lens of the present invention has a coating film composed of an antifogging agent formed on the surface of the plastic lens, and the coating film is formed of an antifogging agent containing a (meth)acrylic polymer. The (meth)acrylic polymer has a repeating unit represented by the formula (I) and has an alkoxyfluorenyl group represented by the formula (II) at least at one end:

(wherein R ¹ represents a hydrogen atom or a methyl group, and R ² represents a hydrophilic group)

(wherein R ³ , R ⁴ and R ⁵ each independently represent an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and at least one of R ³ , R ⁴ and R ⁵ is represented by An alkoxy group having 1 to 4 carbon atoms, and R ^{6 is} an alkylene group having 1 to 12 carbon atoms.

In the repeating unit represented by the formula (I), R ¹ is a hydrogen atom or a methyl group. R ² is a hydrophilic group. The hydrophilic group represented by R ² may, for example, be a group represented by the formula (III), a group represented by the formula (IV), a hydrogen atom, an alkyl group having 1 to 4 carbon atoms having at least one hydroxyl group, and hydrogen at one terminal. a polyglycol group having 1 to 20 carbon atoms of an alkyl group having 1 to 4 carbon atoms, a polypropylene glycol group having 1 to 10 carbon atoms having a hydrogen atom or an alkyl group having 1 to 4 carbon atoms at one end, However, the invention is not limited to this illustration:

(wherein R ⁷ and R ⁸ each independently represent an alkylene group having 1 to 4 carbon atoms, and R ⁹ and R ¹⁰ each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms)

(wherein R ¹¹ represents an alkylene group having 1 to 4 carbon atoms, and R ¹² and R ¹³ each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, R ¹⁴ represents an organic group, and X ^- represents an anion).

Among these bases, from the viewpoint of improving the mechanical strength of the coating film composed of the antifogging agent, it is preferably a group represented by the formula (III) and a group represented by the formula (IV), and more preferably represented by the formula (III). base.

In the formula (III), R ⁷ and R ⁸ are each independently an alkylene group having 1 to 4 carbon atoms. R ^{7 is} preferably a methylene group, an ethyl group, an extended propyl group or an extended isopropyl group, more preferably a methylene group or an ethyl group. R ^{8 is} preferably a methylene group or an ethyl group. R ⁹ and R ¹⁰ are each independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. An alkyl group having 1 to 4 carbon atoms, for example, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a t-butyl group or the like.

In the formula (IV), R ¹¹ is an alkylene group having 1 to 4 carbon atoms. R ^{11 is} preferably a methylene group, an ethyl group, an extended propyl group or an extended isopropyl group, more preferably a methylene group or an ethyl group. R ¹² and R ¹³ are each independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. An alkyl group having 1 to 4 carbon atoms, for example, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a t-butyl group or the like. R ¹⁴ is an organic group. Specific examples of the organic group include an alkyl group having 1 to 22 carbon atoms, an aryl group having 6 to 12 carbon atoms, and a carboxyalkyl group having 2 to 6 carbon atoms. However, the present invention is not limited to the examples. X ^- is an anion. A preferred example of X ^- may be an alkyl chloride ion having 1 to 4 carbon atoms, a dialkyl sulfate ion having a carbon number of 1 to 4, an aryl chloride ion having 6 to 8 carbon atoms, or an alkyl group. The carbon number of the base is 1 to 4 alkylsulfate halide, halogen ion, acetate ion, boric acid ion, citrate ion, tartaric acid ion, hydrogen sulfate ion, bisulfite ion, sulfate ion, phosphate ion, etc., but the present invention Not only this illustration is limited. Examples of the halogen atom of the alkylsulfate halide include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Examples of the halogen ion in the halogen ion include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. X ^- among preferred is alkyl having 1 to 4 of chloride ion, an alkyl group of carbon atoms and a dialkyl sulfate ion having 1 to 4 carbon atoms of the monovalent aromatic group having 6 to 8 of the chloride ion.

The lower limit of the number of repeating units represented by the formula (I) is preferably 1 or more, more preferably 10 or more, from the viewpoint of improving the water resistance of the plastic lens, and the upper limit of the number of repeating units represented by the formula (I) The value is preferably 1000 or less, more preferably 500 or less from the viewpoint of improving the antifogging property of the plastic lens.

In the alkoxyfluorenyl group represented by the formula (II), R ³ , R ⁴ and R ⁵ are each independently an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and R ³ and R ⁴ are each independently And at least one of R ⁵ is an alkoxy group having 1 to 4 carbon atoms. At least one of R ³ , R ⁴ and R ⁵ is an alkoxy group having 1 to 4 carbon atoms and is used for fixing an antifogging agent to a plastic lens by a chemical bond. Therefore, at least one of R ³ , R ⁴ and R ^{5 is} preferably an alkoxy group having 1 to 4 carbon atoms, and at least 2 of R ³ , R ⁴ and R ^{5 are} alkoxy groups having 1 to 4 carbon atoms. More preferably, R ³ , R ⁴ and R ⁵ are each alkoxy groups having 1 to 4 carbon atoms. Among the alkyl groups having 1 to 4 carbon atoms, a methyl group and an ethyl group are preferred, and a methyl group is more preferred. Among the alkoxy groups having 1 to 4 carbon atoms, a methoxy group and an ethoxy group are preferred, and a methoxy group is more preferred.

In the alkoxyfluorenyl group represented by the formula (II), R ⁶ is an alkylene group having 1 to 12 carbon atoms. Among R ⁶ , an alkylene group having 1 to 8 carbon atoms is preferred, an alkylene group having 1 to 6 carbon atoms is more preferable, and an alkylene group having 2 to 6 carbon atoms is more preferable.

The alkoxyfluorenyl group represented by the formula (II) is present at at least one end of the (meth)acrylic polymer, but from the viewpoint of sufficiently exhibiting antifogging property, only one end of the (meth)acrylic polymer is present. good. When the alkoxyfluorenyl group represented by the formula (II) is present only at one end of the (meth)acrylic polymer, The viewpoint of sufficiently exhibiting antifogging property is preferably such that a hydroxyl group, an alkoxy group having 1 to 4 carbon atoms, or a residue of a polymerization initiator is preferably present at the other end.

a (meth)acrylic polymer having a repeating unit represented by the formula (I) and having an alkoxyfluorenyl group represented by the formula (II) at at least one terminal, which may be represented by, for example, the formula (V) The monomer component of the acrylic monomer is polymerized in the presence of a compound containing an alkoxyfluorenyl group represented by the formula (VI):

(wherein R ¹ and R ^{2 are the} same as described above)

(wherein R ³ , R ⁴ , R ⁵ and R ^{6 are the} same as described above)

A (meth)acrylic monomer represented by the formula (V), for example, N-(methyl)propenyloxyethyl-N,N-dimethylammonium-α-N-methylcarboxybetaine, N -(Meth)acryloylaminoethyl-N,N-dimethylammonium-α-N-methylcarboxybetaine, methoxytriethylene glycol (meth)acrylate, methacrylic acid 2, 2,2-trifluoroethyl ester or the like, but the invention is not limited to the examples. These (meth)acrylic monomers may be used alone or in combination of two or more. For example, JP-A-9-95474, and JP-A-9-95586, It is easily prepared by the method described in JP-A-H11-222470 or the like.

Further, the monomer component may contain a polymerizable monomer other than the (meth)acrylic monomer represented by the formula (V) within the range not impairing the object of the present invention.

Other polymerizable monomers such as styrene, α-hydroxystyrene, p-hydroxystyrene, methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, (methyl) ) isobutyl acrylate, tert-butyl (meth)acrylate, neopentyl (meth)acrylate, cyclohexyl (meth)acrylate, benzyl (meth)acrylate, octyl (meth)acrylate, Lauryl (meth)acrylate, stearyl (meth)acrylate, cetyl (meth)acrylate, ethyl carbitol (meth)acrylate, hydroxyethyl (meth)acrylate, (methyl) Hydroxypropyl acrylate, hydroxybutyl (meth) acrylate, methoxyethyl (meth) acrylate, methoxybutyl (meth) acrylate, N-methyl (meth) acrylamide, N -ethyl (meth) acrylamide, N-propyl (meth) acrylamide, N-isopropyl (meth) acrylamide, N-butoxymethyl (meth) acrylamide , N-tert-butyl (meth) acrylamide, N-octyl (meth) acrylamide, N, N-dimethyl (meth) acrylamide, N, N-diethyl ( Methyl) acrylamide, (meth) propylene sulfhydryl Porphyrin, diacetone (meth) acrylamide, styrene, methyl itaconate, ethyl itaconate, vinyl acetate, vinyl propionate, N-vinyl pyrrolidone, N-vinyl caprolactam Etc., but the invention is not limited to this illustration. These other polymerizable monomers may be used alone or in combination of two or more.

The content of the other monomer in the monomer component varies depending on the type of the other monomer, and therefore it cannot be determined in general, and it is preferred to appropriately adjust it within the range not impairing the object of the present invention.

The compound containing an alkoxyfluorenyl group represented by the formula (VI), for example, 3-mercaptopropyltrimethoxydecane, 3-mercaptopropyltriethoxydecane, 3-mercaptopropyltriisopropoxydecane, 3-mercaptopropylmethyldimethoxydecane, 3-mercaptopropylmethyldiethoxydecane, 3-mercaptopropylmethyldipropoxydecane, etc., but the present invention is not limited to this example. These alkoxyfluorenyl group-containing compounds may be used alone or in combination of two or more.

The amount of the alkoxyfluorenyl group-containing compound represented by the formula (VI) is not particularly limited, and from the viewpoint of sufficiently exhibiting water resistance and antifogging property, it is usually contained in an amount of about 0.01 to 10 parts by weight per 100 parts by weight of the monomer component. good.

When the monomer component is polymerized in the presence of a compound containing an alkoxyfluorenyl group represented by the formula (VI), a polymerization initiator is preferably used.

A polymerization initiator such as azoisobutyronitrile, methyl azoisobutyrate, azobisdimethylvaleronitrile, benzammonium peroxide, potassium persulfate, ammonium persulfate, diphenyl ketone derivative A phosphine oxide derivative, a diphenyl ketone derivative, a phenyl sulfide derivative, an azide derivative, a diazo derivative, a disulfide derivative or the like, but the present invention is not limited to the examples. These polymerization initiators may be used alone or in combination of two or more.

The amount of the polymerization initiator is not particularly limited, and is usually preferably from 0.01 to 5 parts by weight per 100 parts by weight of the monomer component.

A method of polymerizing the (meth)acrylic monomer represented by the formula (V), for example, a solution polymerization method, etc., is not limited to the examples. When the monomer component is polymerized by a solution polymerization method, for example, a monomer component and a compound containing an alkoxyfluorenyl group represented by the formula (VI) can be dissolved in a solvent, and a polymerization initiator can be added while stirring the obtained solution. The monomer component is polymerized.

The solvent is, for example, an alcohol such as methanol, ethanol, isopropanol, ethylene glycol or propylene glycol, a ketone such as acetone or methyl ethyl ketone, an ether such as diethyl ether or tetrahydrofuran, an aromatic hydrocarbon compound such as benzene, toluene or xylene, or an aliphatic such as n-hexane. Examples thereof include a hydrocarbon compound, an alicyclic hydrocarbon compound such as cyclohexane, an acetate such as methyl acetate or ethyl acetate, and the like, but the invention is not limited to the examples. These solvents may be used alone or in combination of two or more.

The amount of the solvent is usually preferably adjusted so that the monomer component concentration in the solution obtained by dissolving the monomer component and the alkoxyfluorenyl group-containing compound represented by the formula (VI) in a solvent is about 10~. 80% by weight is preferred.

The polymerization conditions such as the polymerization temperature and the polymerization time in the polymerization of the monomer component are preferably adjusted as appropriate depending on the type of the monomer used for the monomer component, the amount thereof used, the type of the polymerization initiator, and the amount thereof to be used.

The gas atmosphere at the time of polymerizing the monomer component is preferably a passive gas. A passive gas such as nitrogen gas, argon gas or the like is used, but the present invention is not limited to this example.

Whether or not an unreacted monomer is present at the end of the polymerization reaction or in the reaction system can be confirmed by, for example, a general analytical method such as gas chromatography.

By polymerizing the monomer component in the presence of the alkoxyfluorenyl group-containing compound represented by the formula (VI) in the above manner, a (meth)acrylic polymer having an alkoxyfluorenyl group can be obtained.

The viscosity average molecular weight of the (meth)acrylic polymer having an alkoxyfluorenyl group is preferably 100 or more, more preferably 500 or more, from the viewpoint of sufficiently exhibiting a surface modification effect, and is improved from having an alkoxy group. The viewpoint of the solubility of the (meth)acrylic polymer is preferably 100,000 or less, more preferably Below 50000. The viscosity average molecular weight of the (meth)acrylic polymer having an alkoxyfluorenyl group can be obtained by using a Ubbelohde type viscometer [manufactured by Mutual Chemicals Co., Ltd., product number: U-0327-26] at 25 ° C The viscosity of the (meth)acrylic polymer solution was measured and found by gel permeation chromatography.

A (meth)acrylic polymer having the above alkoxyfluorenyl group. The antifogging agent may be composed only of the (meth)acrylic polymer having an alkoxyfluorenyl group, or may contain a solvent.

The solvent is, for example, an alcohol such as methanol, ethanol, isopropanol, ethylene glycol or propylene glycol, a ketone such as acetone or methyl ethyl ketone, an ether such as diethyl ether or tetrahydrofuran, an aromatic hydrocarbon compound such as benzene, toluene or xylene, or an aliphatic such as n-hexane. Examples thereof include a hydrocarbon compound, an alicyclic hydrocarbon compound such as cyclohexane, an acetate such as methyl acetate or ethyl acetate, and the like, but the invention is not limited to the examples. These solvents may be used alone or in combination of two or more.

The amount of the solvent is not particularly limited, and it is usually adjusted to a (meth)acrylic polymer having an alkoxyfluorenyl group in a solution obtained by dissolving a (meth)acrylic polymer having an alkoxyfluorenyl group in a solvent. The concentration is preferably about 10 to 80% by weight.

The aforementioned antifogging agent is desirably used as an antifogging agent for plastic lenses. The antifogging plastic lens of the present invention can be produced, for example, by forming a coating film made of an antifogging agent on the surface of a plastic mirror surface by applying an antifogging agent to a plastic lens or the like.

A resin constituting a plastic lens, such as an acrylic resin, a polystyrene resin, a polychlorinated vinyl resin, or a polyamine-based tree represented by nylon A fat, a polyimide resin, a polyvinyl alcohol resin, a vinyl acetate resin, a polycarbonate resin, a polyester resin, a polyether resin, or the like, but the present invention is not limited to this example. Further, the size and shape of the plastic lens are not particularly limited, and may be appropriately determined depending on the use thereof.

From the viewpoint that the above-mentioned antifogging agent is firmly fixed to a plastic lens having a hydroxyl group on the surface, it is preferable that a plastic lens having a hydroxyl group on the surface is preferable. When a plastic lens having no hydroxyl group on its surface is used, it is preferred to modify the surface so that a hydroxyl group is preferably present on the surface thereof.

From the viewpoint of imparting antireflection properties, it is preferred that the surface of the plastic lens is formed of an antireflection layer composed of an antireflection agent. In this case, it is preferable that the coating film composed of the antifogging agent is formed on the antireflection layer.

The antireflection agent is, for example, a fluorine-containing compound, an organic antireflective agent containing a decane compound, or an inorganic antireflective agent containing cerium oxide or the like. Among the antireflection agents, the antifogging agent has an excellent property of being strongly bonded to an inorganic antireflective agent. Among the inorganic antireflective agents, an inorganic antireflective agent containing cerium oxide is preferred from the viewpoint of firmly bonding the antifogging agent.

The method of forming the antireflection layer on the surface of the plastic lens varies depending on the type of the antireflection agent, and therefore cannot be determined uniformly, and it should be appropriately determined depending on the type of the antireflection agent. A method of forming an antireflective agent on the surface of a plastic lens. For example, when an antireflective agent is an organic antireflective agent, a solution or dispersion of the organic antireflective agent is applied to the surface of the plastic lens. The method of formation, etc. Further, in the case where an antireflective agent is an inorganic antireflective agent, for example, a vacuum deposition method, a sputtering method, or a chemical method may be mentioned. A method of depositing an inorganic antireflective agent on the surface of a plastic lens by vapor deposition or the like to form an antireflection layer on the surface of the plastic lens, but the present invention is not limited to this example. For example, when the cerium oxide is vapor-deposited on the surface of the plastic lens by vacuum evaporation, the alkoxy decane such as tetramethoxy decane can be obtained by placing the plastic lens in a vacuum container and deaerating under heating. Vapor is introduced into the vacuum vessel, and cerium oxide is evaporated on the surface of the plastic lens to form an antireflection layer.

The amount of anti-reflective layer formed on the surface of the plastic lens depends on the type of anti-reflective agent, the type of resin used in the plastic lens, etc., so it cannot be determined in general, and should be used depending on the type of anti-reflective agent and plastic lens. The type of the resin or the like is appropriately determined. The amount of the antireflection layer formed on the surface of the plastic lens is usually an amount sufficient to impart antireflection to the plastic lens and to form a uniform antireflection layer.

Examples of the method of applying the antifogging agent to the plastic lens include a flow coating method, a spray coating method, a dipping method, a brush coating method, a roll coating method, and the like, but the present invention is not limited to the examples.

The gas atmosphere when the antifogging agent is applied to the plastic lens is usually atmospheric. Further, the temperature at which the antifogging agent is applied to the plastic lens may be usually normal temperature or heated. The amount of the anti-fogging agent applied to the plastic lens when the anti-fogging agent is applied to the plastic lens depends on the use of the plastic lens, and therefore cannot be determined uniformly, and should be appropriately adjusted depending on the use thereof. After the anti-fogging agent is applied to the plastic lens, it is preferable to heat the plastic lens from the viewpoint of improving production efficiency. The heating temperature of the plastic lens varies depending on the heat-resistant temperature of the plastic lens, so it cannot be determined uniformly, but it is usually in the range of 50 to 150 °C. It is preferred to select a temperature suitable for the plastic lens.

By applying the antifogging agent to the plastic lens in the above manner, a coating film composed of an antifogging agent can be formed on the surface of the plastic lens.

The thickness of the coating film composed of the antifogging agent formed on the surface of the plastic lens is preferably 10 nm or more from the viewpoint of sufficiently imparting antifogging property, and is preferably 100 nm or less from the viewpoint of maintaining the antireflection property of the plastic lens.

As described above, since the antifogging plastic lens of the present invention has a coating film composed of the antifogging agent formed on the surface thereof, it is excellent in water resistance and antifogging property, and can prevent when a conventional surfactant is used. The coating film is lost when moisture adheres. Therefore, the antifogging plastic lens of the present invention is not easily deteriorated in antifogging property even when it comes into contact with water, so that excellent antifogging property can be maintained. Furthermore, the antifogging plastic lens of the present invention does not impair the antireflection property of the antireflection layer when it forms an antireflection layer on the surface of the lens, and has excellent antifogging property and excellent water resistance.

Example

Next, the present invention will be described in more detail based on examples, but the present invention is not limited to the examples.

Example 1

Add N-methyl propylene oxirane-N,N-dimethylammonium-α-N-methylcarboxybetaine to a 500 mL flask equipped with a nitrogen gas introduction tube, a condenser, and a stirrer [Osaka Organic Chemistry Industrial (stock) system, trade name: GLBT] 32.31 g, 3-mercaptopropyltrimethoxydecane [manufactured by Shin-Etsu Chemical Co., Ltd., trade name: KBM-803] 1.55 g and ethanol 146.20 g. After depressurizing the inside of the flask to degas, introduce nitrogen into the flask and return to normal pressure, as much as possible Exclude oxygen from the flask.

Next, the contents of the flask were heated to 65 ° C by an oil bath attached to the flask, and then 1.83 g of azobisisobutyronitrile was added, and the temperature of the contents of the flask was maintained at 70 ° C for 4 hours. Thereafter, 0.37 g of azobisisobutyronitrile was added to the flask, and the mixture was aged for 4 hours while maintaining the reaction temperature at 70 ° C to obtain a polymer solution.

The obtained polymer solution was cooled to 30 ° C in a water bath and diluted with 182.76 g of ethanol to obtain a (meth)acrylic polymer solution having an alkoxyfluorenyl group.

The (meth)acrylic polymer solution having an alkoxyfluorenyl group was obtained by a Ubbelohde type viscometer [manufactured by Mutual Chemicals Co., Ltd., product number: U-0327-26] at 25 ° C. The viscosity and the viscosity average molecular weight were obtained, and as a result, the average molecular weight of the viscosity was 15,000. This (meth)acrylic polymer solution having an alkoxyfluorenyl group is used as an antifogging agent.

On the other hand, a plastic lens made of an acrylic resin (convex lens, diameter: 40 mm, thickness of the central portion of the lens: 1 mm) was placed in a vacuum vessel, and after degassing, a vapor of trimethoxydecane (vapor pressure: about 400 Pa) was introduced. The plastic lens was vapor-deposited with cerium oxide for 3 hours.

Next, on the plastic lens on which the cerium oxide is vapor-deposited, the anti-fogging agent obtained by the above is applied by flow coating, and the excess anti-fogging agent is washed with ethanol to be removed, and then the plastic lens is placed in a warm air drying. In the machine, the air was dried at a temperature of 80 ° C for 30 minutes to obtain an anti-fog plastic lens.

Example 2

Add N-methyl propylene oxiranyl-N,N-dimethylammonium-α-N-methylcarboxybetaine to a 500 mL flask equipped with a nitrogen gas introduction tube, a condenser, and a stirrer [Osaka Organic Chemistry Industrial (stock) system, trade name: GLBT] 35.00 g, 3-mercaptopropyltrimethoxydecane [manufactured by Shin-Etsu Chemical Co., Ltd., trade name: KBM-803] 3.27 g and ethanol 153.10 g. After the inside of the flask was depressurized to degas, nitrogen gas was introduced into the flask and returned to normal pressure, and oxygen in the flask was excluded as much as possible.

Next, the contents of the flask were heated to 65 ° C in an oil bath attached to the flask, and then 0.38 g of azobisisobutyronitrile was added thereto, and the temperature of the contents of the flask was maintained at 70 ° C for 4 hours. Thereafter, 0.38 g of azobisisobutyronitrile was added to the flask, and the mixture was aged for 4 hours while maintaining the reaction temperature at 70 ° C to obtain a polymer solution.

The obtained polymer solution was cooled to 30 ° C in a water bath and diluted with 191.37 g of ethanol to obtain a (meth)acrylic polymer solution having an alkoxyfluorenyl group. This (meth)acrylic polymer solution having an alkoxyfluorenyl group is used as an antifogging agent.

The viscosity of the obtained (meth)acrylic polymer solution having an alkoxyfluorenyl group was measured in the same manner as in Example 1 to obtain a viscosity average molecular weight, and as a result, the viscosity average molecular weight was 3,000.

Next, using the anti-fogging agent obtained as described above, an anti-fogging agent was applied to the plastic lens on which the cerium oxide was vapor-deposited in the same manner as in Example 1 to obtain an anti-fogging plastic lens.

Example 3

500mL with a nitrogen inlet, condenser and mixer N-methyl propylene oxiranyl-N,N-dimethylammonium-α-N-methylcarboxybetaine [Osaka Organic Chemical Industry Co., Ltd., trade name: GLBT] was added to the flask, 35.00 g, 3-mercaptopropyltrimethoxydecane [manufactured by Shin-Etsu Chemical Co., Ltd., trade name: KBM-803] 0.75 g and ethanol 143.02 g. After the inside of the flask was depressurized to degas, nitrogen gas was introduced into the flask and returned to normal pressure, and oxygen in the flask was excluded as much as possible.

Next, the contents of the flask were heated to 65 ° C in an oil bath attached to the flask, and then 0.89 g of azobisisobutyronitrile was added thereto, and the temperature of the contents of the flask was maintained at 70 ° C for 4 hours. Then, 0.36 g of azobisisobutyronitrile was added to the flask, and the mixture was aged for 4 hours while maintaining the reaction temperature at 70 ° C to obtain a polymer solution.

The obtained polymer solution was cooled to 30 ° C in a water bath and diluted with 178.78 g of ethanol to obtain a (meth)acrylic polymer solution having an alkoxyfluorenyl group.

The viscosity of the obtained (meth)acrylic polymer solution having an alkoxyfluorenyl group was measured in the same manner as in Example 1 to obtain a viscosity average molecular weight, and as a result, the viscosity average molecular weight was 5,000. This (meth)acrylic polymer solution having an alkoxyfluorenyl group is used as an antifogging agent.

Next, using the anti-fogging agent obtained as described above, an anti-fogging agent was applied to the plastic lens on which the cerium oxide was vapor-deposited in the same manner as in Example 1 to obtain an anti-fogging plastic lens.

Comparative example 1

In the first embodiment, a plastic lens in which a coating film composed of an antifogging agent was not formed was used.

Comparative example 2

A 1% sodium laurate aqueous solution was applied to a plastic lens deposited with cerium oxide in the same manner as in Example 1, and the plastic lens was placed in a warm air dryer at a temperature of 80 ° C for 30 minutes. The air is dried to obtain an anti-fog plastic lens.

N-methylpropenyloxyethyl-N,N-dimethylammonium-α-N-methylcarboxybetaine monohydrate was added to a 1 L flask equipped with a nitrogen gas introduction tube, a condenser and a stirrer [ Osaka Organic Chemical Industry Co., Ltd., trade name: GLBT] 25.0 g, γ-methyl propylene methoxypropyl trimethoxy decane [Shin-Etsu Chemical Co., Ltd., trade name: KBM-503] 30.6 g and ethanol 500.3 g. After depressurizing the inside of the flask to degas, nitrogen gas was introduced into the flask and returned to normal pressure.

Next, 2.8 g of azobisisobutyronitrile was added to the flask, and the temperature of the contents of the flask was maintained at 70 ° C for 8 hours, and then cooled to 30 ° C in a water bath to obtain a (meth)acrylic polymer solution ( The content of the solid content of the resin: 10% by mass). The viscosity of the obtained (meth)acrylic polymer solution was measured at 25 ° C using an Ubbelohde type viscometer [manufactured by Mutual Chemicals Co., Ltd., product number: U-0327-26] to obtain a viscosity average molecular weight. As a result, the viscosity average molecular weight was 39,000.

The obtained (meth)acrylic polymer solution was coated on the cerium oxide-deposited plastic lens manufactured in the same manner as in Example 1 to obtain an antifogging agent treated with a moisture-absorbing antifogging agent. Plastic lenses.

Next, in view of the physical properties of the anti-fog plastic lens or the plastic lens obtained as described above, the anti-fog property, water resistance, anti-reflection property and coating were evaluated according to the following methods. The thickness of the film. The results are shown in Table 1.

(1) Anti-fog property

The coating film composed of the antifogging agent formed on the antifogging plastic lens was exposed to a humidified environment (temperature: 30° C., relative humidity: 90%) for 30 seconds, and was visually observed to be composed of an antifogging agent. The plastic lens of the coated film was easy to see and evaluated based on the following evaluation criteria.

(evaluation benchmark)

○: The plastic lens can be clearly seen.

△: The plastic lens can be seen slightly blurred.

×: The plastic lens is foggy and invisible.

(2) Water resistance

After immersing the antifogging plastic lens in hot water heated to 80° C. for 30 minutes, the visibility of the plastic lens with the coating film formed of the antifogging agent was visually observed, and the evaluation was performed based on the following evaluation criteria. .

(evaluation benchmark)

○: The plastic lens can be clearly seen.

△: The plastic lens can be seen slightly blurred.

×: The plastic lens is foggy and invisible.

(3) Anti-reflection

The anti-fog plastic lens was irradiated with monochromatic light to visually observe whether interference fringes were generated at this time, and evaluated according to the following evaluation criteria.

(evaluation benchmark)

○: The interference fringes were hardly seen.

△: The interference fringes are slightly visible.

×: Interference fringes were clearly observed.

(4) Thickness of the coating film

The thickness of the coating film composed of the antifogging agent formed on the antifogging plastic lens was measured using a stylus type height difference meter [KLA-Tencor Co., Ltd., product number: P-10].

As is apparent from the results shown in Table 1, the antifogging plastic lenses obtained in the respective examples were excellent in water resistance, and were not easily detached from the plastic lens even in contact with water, and were excellent in antifogging property. Furthermore, it can be seen that the anti-fog plastic lenses obtained in the respective embodiments all have an anti-reflection property against the anti-reflection film even when an anti-reflection film is formed on the surface of the lens, and have excellent water resistance and anti-fog. Sex.

Claims (7)

An anti-fog plastic lens having a coating film made of an anti-fogging agent formed on a surface of a plastic lens, wherein the coating film is formed of an anti-fogging agent containing a (meth)acrylic polymer, The (meth)acrylic polymer has a repeating unit represented by the formula (I) and has an alkoxyfluorenyl group represented by the formula (II) at least at one end: (wherein R ¹ represents a hydrogen atom or a methyl group, and R ² represents a hydrophilic group) (wherein R ³ , R ⁴ and R ⁵ each independently represent an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and at least one of R ³ , R ⁴ and R ⁵ is represented by An alkoxy group having 1 to 4 carbon atoms, and R ^{6 is} an alkylene group having 1 to 12 carbon atoms. An antifogging plastic lens according to the first aspect of the invention, wherein, in the formula (I), R ² represents a hydrophilic group of the formula (III), a group represented by the formula (IV), a hydrogen atom, and At least one hydroxyl group having 1 to 4 carbon atoms, a terminal having a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and having a carbon number of 1 to 20, having a hydrogen atom or a carbon number at one end a polypropylene glycol having 1 to 10 carbon atoms of 1 to 10: (wherein R ⁷ and R ⁸ each independently represent an alkylene group having 1 to 4 carbon atoms, and R ⁹ and R ¹⁰ each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms) (wherein R ¹¹ represents an alkylene group having 1 to 4 carbon atoms, and R ¹² and R ¹³ each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, R ¹⁴ represents an organic group, and X ^- represents an anion). An anti-fog plastic lens according to claim 1 or 2, wherein the number of repeating units represented by the formula (I) is from 1 to 1,000. An antifogging plastic lens according to any one of claims 1 to 3, which is formed by forming a coating film composed of an antifogging agent on an antireflection film formed on a surface of a plastic lens. An antifogging agent comprising: a (meth)acrylic polymer having a repeating unit represented by the formula (I) and having an alkane represented by the formula (II) at at least one terminal Oxycarbonyl group: (wherein R ¹ represents a hydrogen atom or a methyl group, and R ² represents a hydrophilic group) (wherein R ³ , R ⁴ and R ⁵ each independently represent an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and at least one of R ³ , R ⁴ and R ⁵ is represented by It is an alkoxy group having 1 to 4 carbon atoms, and R ⁶ represents an alkylene group having 1 to 12 carbon atoms. An anti-fogging agent according to claim 5, wherein, in the formula (I), R ² is a group represented by the formula (III), a group represented by the formula (IV), a hydrogen atom, and a carbon number having at least one hydroxyl group; a alkyl group of ~4, a polyglycol group having 1 to 20 carbon atoms at a terminal or a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and a hydrogen atom or an alkyl group having 1 to 4 carbon atoms at one terminal. Polypropylene glycol with 1 to 10 carbon atoms: (wherein R ⁷ and R ⁸ each independently represent an alkylene group having 1 to 4 carbon atoms, and R ⁹ and R ¹⁰ each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms) (wherein R ¹¹ represents an alkylene group having 1 to 4 carbon atoms, and R ¹² and R ¹³ each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; R ¹⁴ represents an organic group; and X ^- represents an anion). An anti-fogging agent according to claim 5 or 6, wherein the number of repeating units represented by the formula (I) is from 1 to 1,000.