JP2012190019A - Method for producing dyed plastic lens - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a method for producing a dyed plastic lens which uses a metal-containing dye, which is difficult to dye a plastic lens by the conventional methods, can be uniformly dyed and is excellent in weather resistance.SOLUTION: In a method for producing a dyed plastic lens, a dyeing solution that contains a metal-containing dye, an amphipathic solvent and water and has a pH value of 3.0-6.5 at 25°C is brought into contact with a plastic lens to perform dyeing under the conditions of temperature 90-140°C and pressure 0.5-5.0 MPa.

Description

  The present invention relates to a method for producing a dyed plastic lens. More specifically, the present invention relates to a method for producing a dyed plastic lens that is uniformly dyed and excellent in weather resistance using a metal-containing dye, which has been difficult to dye plastic lenses by a conventional method.

Conventionally, immersion dyeing, pressure dyeing, dye film heating, and the like have been used for dyeing plastic lenses for spectacles. Among these dyeing methods, the immersion dyeing method is a convenient dyeing method because the process is simple and the penetration of the dye into a plastic lens having a refractive index of about 1.5 to 1.6 is easy. (For example, see Patent Documents 1 and 2).
Disperse dyes are mainly used as dyes for dyeing plastic lenses, and they are used in various dyeing methods including immersion dyeing. For example, Patent Document 1 discloses a method for producing a colored plastic lens that is immersed in a dye dispersion bath containing a disperse dye and a carrier made of a halogenated aromatic hydrocarbon. Patent Document 2 discloses a method in which a thermoplastic resin used for a plastic lens or the like is dyed by immersing it in a dyeing solution containing a disperse dye and a monocyclic monoterpene.
However, plastic lenses dyed with disperse dyes may fade during long-term use, and further improvement in the weather resistance of dyed plastic lenses is desired.
Therefore, it is conceivable to improve the weather resistance of the dyed plastic lens by using a dye having a better weather resistance than the disperse dye. Metal-containing dyes are known as dyes having excellent weather resistance.

Japanese Patent Laid-Open No. 11-248901 JP 2004-2690 A

However, even when the dyeing method described in Patent Documents 1 and 2 is used and the disperse dye is replaced with a metal-containing dye, the plastic lens cannot be dyed.
An object of the present invention is to provide a method for producing a dyed plastic lens excellent in weather resistance, which is uniformly dyed using a metal-containing dye, which has been difficult to dye plastic lenses by conventional methods.

As a result of intensive studies, the present inventors have found that the above problem can be solved by dyeing plastic lenses under specific conditions.
That is, the present invention comprises a metal-containing dye, an amphiphilic solvent, and water, and a staining solution having a pH of 3.0 to 6.5 at 25 ° C. and a plastic lens are brought into contact with each other at a temperature of 90 to 140 ° C. It is a manufacturing method of the dyeing plastic lens dye | stained on the conditions of a pressure of 0.5-5.0 MPa.

  According to the present invention, even when a metal-containing dye is used, it is possible to dye a plastic lens, and it is possible to provide a dyed plastic lens that is uniformly dyed and excellent in weather resistance. The obtained stained plastic lens is suitably used for spectacle lenses, camera lenses, projector lenses, telescope lenses, magnifier lenses, and the like.

  The present invention comprises a metal-containing dye, an amphiphilic solvent, and water, and a dyeing solution having a pH of 3.0 to 6.5 at 25 ° C. and a plastic lens are brought into contact with each other at a temperature of 90 to 140 ° C. and a pressure. It is a manufacturing method of the dyeing plastic lens dye | stained on the conditions of 0.5-5.0 MPa.

The mechanism of dyeing plastic lenses with metal-containing dyes is thought to be the adsorption of metal-containing dyes to plastic lenses and / or the dyeing by the formation of chemical bonds between functional groups present in plastic lenses and metal-containing dyes. It is done.
A plastic lens used as a spectacle lens is molded by cast polymerization using, for example, a thermosetting resin. Here, when a thermosetting resin having high reactivity is used, the reaction is fast and the composition is likely to be non-uniform. In particular, in the portion near the resin injection port of the molded lens, a crystalline region and an amorphous region Is likely to occur. When such a lens is dyed by a conventional method using a disperse dye, the disperse dye dyed by penetrating into the lens has a difference in dyeing degree between the crystalline region and the non-crystalline region of the lens, Uneven dyeing occurs.
On the other hand, when dyed with a metal-containing dye under specific conditions, even if there are crystalline and non-crystalline regions in the plastic lens, a uniformly stained plastic lens is obtained without causing uneven dyeing. I found out that

  In the method for producing a dyed plastic lens according to the present invention, the dyeing solution is allowed to act on the plastic lens under a specific range of temperature and pressure conditions, whereby the metal-containing dye in the dyeing solution is adsorbed to the plastic lens and / or the metal-containing material. It is considered that chemical bond formation between the dye and the plastic lens is promoted.

<Plastic lens>
The material of the plastic lens used in the present invention is not particularly limited. For example, it is generally used for a lens made of a thermoplastic resin that can be molded by an injection molding method, a spectacle lens that can be molded by casting polymerization, or the like. A lens made of a thermosetting resin can be used.
Examples of the material of the plastic lens include, for example, methyl methacrylate homopolymer, copolymer of methyl methacrylate and one or more other monomers, diethylene glycol bisallyl carbonate homopolymer, diethylene glycol bisallyl carbonate and one or more other. A copolymer of the above monomers, an acrylonitrile-styrene copolymer, a halogen-containing copolymer, a homopolymer of a monomer having a sulfide bond, a copolymer of a monomer having a sulfide bond and one or more other monomers, Examples include polyurea resin, polycarbonate resin, polystyrene resin, polyolefin resin, polyvinyl chloride resin, polyester resin, polyethylene terephthalate, polyurethane resin, polythiourethane resin, and epoxy resin.
Among these, a plastic lens made of polyurea resin or polythiourethane resin is preferably used, and a plastic lens made of polyurea resin is more preferably used. This is because the plastic lens made of polyurea resin has an amino group which is a functional group capable of forming a chemical bond with the metal in the metal-containing dye, and thus the metal-containing dye is easily dyed. The functional group capable of forming a chemical bond with the metal in the metal-containing dye will be described later.
The shape of the plastic lens is not particularly limited. For example, a plastic lens having various curved surfaces such as a spherical surface, a rotationally symmetric aspherical surface, a multifocal lens, an aspherical surface such as a toric surface, a convex surface, and a concave surface can be used.
The plastic lens molding method is not particularly limited, and a plastic lens molded by an injection molding method, a molding method using casting polymerization, or the like can be used according to the material or shape of the lens.

The plastic lens used in the present invention preferably has a functional group capable of forming a chemical bond with the metal in the metal-containing dye from the viewpoint of uniformly dyeing the plastic lens.
The functional group may be any functional group that can form a chemical bond such as an ionic bond or a coordinate bond with the metal in the metal-containing dye. Among these, from the viewpoint of easily forming a chemical bond with the metal in the metal-containing dye, the functional group is preferably at least one selected from an amino group and a carboxyl group, and more preferably an amino group. preferable. The plastic lens may have one or more of these functional groups.

  Examples of commercially available plastic lenses used in the present invention include Phoenix (made by HOYA), which is a plastic lens made of polyurea resin, EYAS (made by HOYA), which is a plastic lens made of polythiourethane resin, and the like. Is mentioned.

<Dyeing liquid>
In the method for producing a dyed plastic lens of the present invention, a dye solution containing a metal-containing dye, an amphiphilic solvent, and water and having a pH of 3.0 to 6.5 at 25 ° C. is used. Hereinafter, each component contained in the staining liquid will be described.

(Metallic dyes)
The dyeing liquid used in the present invention contains a metal-containing dye as a dye. The metal-containing dye is a dye containing a heavy metal cation in the form of a complex salt in the molecule, and examples thereof include metal azo complex dyes. Examples of metal azo complex dyes include complex salts of heavy metal cations such as chromium, copper, nickel, cobalt, iron, and antimony with dyes having an azobenzene structure such as o, o′-dihydroxyazobenzene. A metal-containing dye can be used individually or in combination of 2 or more types.
Since metal-containing dyes are excellent in weather resistance, dyed plastic lenses dyed with metal-containing dyes exhibit excellent weather resistance.

  Examples of commercially available metal-containing dyes used in the present invention include Kayakalan Bordeaux BL (manufactured by Nippon Kayaku Co., Ltd.), Kayakalan Gray BL 167 (manufactured by Nippon Kayaku Co., Ltd.), Kayakalan OLive (manufactured by Nippon Kayaku Co., Ltd.). ) And the like.

  The content of the metal-containing dye in the dyeing liquid is not particularly limited, but is preferably 0.01 to 2.0% by mass, more preferably 0.1 to 1.0% by mass. If the content of the metal-containing dye in the dyeing liquid is in the range of 0.01 to 2.0% by mass, the plastic lens can be dyed efficiently.

(Amphiphilic solvent)
The dyeing liquid used in the present invention contains an amphiphilic solvent as an essential component.
Both plastic lenses and disperse dyes used in the past have a high degree of hydrophobicity, so both have high affinity. However, since metal-containing dyes are hydrophilic, they have an affinity for plastic lenses with high hydrophobicity. Therefore, an amphiphilic solvent having a carrier effect of a metal-containing dye is required.
The amphiphilic solvent has solubility in water, solubility of metal-containing dyes and carrier agents such as monocyclic monoterpenes which are optional components described later, and there is no damage to the plastic lens to be dyed. Any material can be used without particular limitation. Examples of the amphiphilic solvent include methanol, ethanol, propanol, isopropyl alcohol, butanol, isobutyl alcohol, tert-butyl alcohol, pentanol, hexanol, cyclohexanol, benzyl alcohol, ethylene glycol, propylene glycol, diethylene glycol, and dipropylene glycol. , Triethylene glycol, tripropylene glycol, methoxyethanol, ethoxyethanol, propoxyethanol, butoxyethanol, butoxyethoxyethanol, alcohols such as methoxypropanol, ethoxypropanol, propoxypropanol, butoxypropanol, methyl acetate, ethyl acetate, propyl acetate, Esters such as butyl acetate, acetone, methyl ethyl keto , Methyl isobutyl ketone and cyclohexanone and the like.
Among these, at least one selected from alcohols having 1 to 7 carbon atoms is preferable from the viewpoint of high solubility in water and difficulty in swelling the plastic lens. Ethanol, isopropyl alcohol, ethoxy More preferred is butoxyethanol.
These amphiphilic solvents can be used alone or in combination of two or more.
The content of the amphiphilic solvent in the staining solution is preferably 1 to 30% by mass, more preferably 10 to 15% by mass, from the viewpoint that the effect as a carrier can be obtained without fear of damaging the plastic lens. It is.

(Other ingredients)
The staining solution used in the present invention may optionally contain an organic solvent other than the above components, a surfactant, a carrier agent, and an amphiphilic solvent, from the viewpoint of uniformly staining the plastic lens. Good.
The surfactant is not particularly limited and may be a conventionally known surfactant. However, when a carrier agent such as a monocyclic monoterpene described later is used as an optional component, the monocyclic monoterpene is stably used. From the viewpoint of emulsification, an anionic or nonionic surfactant is preferable, and a polyoxyethylene structure is more preferable. Examples of the anionic surfactant include alkylbenzene sulfonate, alkyl naphthalene sulfonate, alkyl sulfosuccinate, aromatic sulfonic acid formalin condensate, and lauryl sulfate. Nonionic surfactants include polyoxy Examples include ethyl alkyl ether, alkyl amine ether, polyoxyethylene sorbitan fatty acid ester and the like. These can be used alone or in combination of two or more.

  When the surfactant is contained in the staining liquid, the content of the anionic surfactant is preferably 0.0001 to 1% by mass, more preferably 0.01 to 0.1% by mass in the staining liquid. Further, the content of the nonionic surfactant is preferably 0.0001 to 1% by mass, more preferably 0.01 to 0.1% by mass in the dyeing solution. When the content of the surfactant is within the above range, the plastic lens can be more uniformly dyed.

  The carrier agent is not particularly limited as long as it can permeate the metal-containing dye into the plastic lens without damaging the plastic lens. From the viewpoint that the plastic lens can be uniformly and efficiently dyed, the monocyclic monoterpene can be used. Is preferred. Examples of monocyclic monoterpenes include limonene, menthol, terpinene, ferrandrene, sylvestrene, pinene and terpineol. These carrier agents can be used alone or in combination of two or more.

(PH)
The pH of the staining solution used in the present invention is 3.0 to 6.5 at 25 ° C. If the pH is outside the above range, the plastic lens cannot be dyed, and the plastic lens may be damaged during dyeing.
The pH is preferably in the range of 4.0 to 6.5 at 25 ° C. in order to ionize the metal-containing dye and efficiently dye the plastic lens without damaging the plastic lens.
The pH adjustment can be performed using a pH adjuster such as acetic acid or sodium acetate.

[Production method of dyed plastic lens]
In the method for producing a dyed plastic lens of the present invention, the dyeing solution and the plastic lens are brought into contact with each other, and dyeing is performed under conditions of a temperature of 90 to 140 ° C. and a pressure of 0.5 to 5.0 MPa. Thereby, the dyeing | staining plastic lens which was dye | stained uniformly and excellent in a weather resistance can be obtained. Hereinafter, a method for manufacturing a dyed plastic lens will be described.

<Preparation of staining solution>
The dyeing liquid is prepared by mixing a metal-containing dye, an amphiphilic solvent, water, and other optional components. There are no particular restrictions on the mixing order and mixing method of each component, and for example, a known method such as mixing the above components contained in the dyeing solution and stirring with a stirrer can be used.
Moreover, it adjusts so that pH at 25 degreeC of the said dyeing | staining liquid may be set to 3.0-6.5 by using a pH adjuster as needed.

<Pretreatment of plastic lens>
The plastic lens to be dyed may be subjected to a pretreatment such as a cleaning treatment and / or a surface treatment before being immersed in the dyeing solution from the viewpoint of enhancing the affinity with the metal-containing dye and uniformly dyeing the plastic lens.
Examples of the cleaning treatment include ozone treatment and plasma treatment. If the surface to be dyed is subjected to ozone treatment or plasma treatment, organic substances adhering to the lens surface will be removed and the hydrophilicity of the plastic lens surface will be increased. It is considered that the affinity with the lens surface is improved.
There is no particular limitation on the ozone treatment and the plasma treatment, and the cleaning treatment may be performed using a known ozone treatment apparatus or plasma treatment apparatus. The plasma output in the plasma treatment is preferably 50 to 500 W, more preferably 100 to 300 W, still more preferably 200 to 300 W, and the degree of vacuum is preferably substantially under vacuum (for example, a degree of vacuum of 1 × 10 ⁻³ to 1 ×). 10 ⁴ Pa, more preferably 1 × 10 ⁻³ to 1 × 10 ³ Pa, and still more preferably 1 × 10 ^{−2 to} 5 × 10 ² Pa). If the plasma output and the degree of vacuum are within this range, the plastic lens is sufficiently cleaned.
From the viewpoint of the cleaning effect, it is preferable to dye the plastic lens immediately after performing the above treatment.

<Dyeing of plastic lenses>
The dyeing solution prepared as described above is brought into contact with the pre-treated plastic lens as necessary, and dyeing is performed under conditions of a temperature of 90 to 140 ° C. and a pressure of 0.5 to 5.0 MPa. Under the above conditions, the plastic lens can be uniformly and efficiently dyed with the metal-containing dye without causing the modification and deformation of the plastic lens due to heating and pressurization.
The method for bringing the staining solution and the plastic lens into contact with each other is not particularly limited, and the staining solution may be attached to the surface of the plastic lens, or the plastic lens may be dyed while being immersed in the staining solution.
The temperature at which the plastic lens is dyed is preferably 95 to 130 ° C., more preferably 100 to 125 ° C., from the viewpoint of uniformly and efficiently dyeing the plastic lens. Moreover, the pressure at the time of dyeing a plastic lens becomes like this from a viewpoint similar to the above, Preferably it is 0.8-3.0 MPa, More preferably, it is 1.0-2.0 MPa.
The dyeing time may be appropriately selected depending on the material of the lens, the type of the metal-containing dye, the type of the amphiphilic solvent, etc., but is preferably 5 to 120 minutes, more preferably 5 to 60 minutes.
The dyeing can be performed using an apparatus such as an autoclave.

[Dyed plastic lens]
The dyed plastic lens manufactured as described above is uniformly dyed and has excellent weather resistance. For example, as a spectacle lens, a camera lens, a projector lens, a telescope lens, a magnifying lens, etc. Useful.
The dyeing density and weather resistance of the dyed plastic lens obtained can be measured by the methods described in the examples. In addition, the dyeing | staining density | concentration of a plastic lens can be suitably selected according to the use and required characteristic of a dyeing plastic lens.

  EXAMPLES Hereinafter, although an Example demonstrates this invention further in detail, this invention is not limited to these Examples. Various physical properties of the dyed plastic lens were evaluated by the following evaluation methods.

(1) Dyeing density After dyeing a plastic lens by the method described in Examples and Comparative Examples, transmission of the dyed plastic lens at a wavelength of 550 nm using a spectrophotometer (manufactured by Hitachi, Ltd., model number: U3410) The rate t (%) was measured, and the staining density (%) was determined from the following equation. In addition, the transmittance | permeability in wavelength 550nm of the plastic lens before dyeing was set to t0 (%).
Staining density (%) = t0−t

(2) Dyeing uniformity The appearance of the stained plastic lens dyed by the method described in the examples and comparative examples is visually observed, and if the surface roughness or unevenness of the lens is not observed, “pass”, surface roughness and / or Those with uneven dyeing were evaluated as “fail”.

(3) Weather resistance evaluation After dyeing a plastic lens by the method described in Examples and Comparative Examples, the lens is divided into two parts, and one side is xenon long life weather meter (manufactured by Suga Test Instruments Co., Ltd., model number: WEL-25AX-). HC / B / EC) was used to conduct a light resistance acceleration test for 200 hours. After the implementation, the light resistance accelerated test was not visually observed, and those that did not show fading were evaluated as “pass”, and those that were fading were evaluated as “fail”.

(4) Lens shape evaluation After the plastic lens was dyed by the methods described in Examples and Comparative Examples, the lens shape change (presence or absence of deformation) was visually observed. Those that maintained the lens shape before dyeing were evaluated as “pass”, and those in which the lens was deformed were evaluated as “fail”.

Preparation Example 1 (Preparation of staining solution 1)
After mixing 1.0 g of metal-containing dye “Kayakalan Bordeaux BL” (manufactured by Nippon Kayaku Co., Ltd.) and 30.0 g of isopropyl alcohol which is an amphiphilic solvent, water was added to this solution to make the total amount 240 mL. . Using acetic acid, the pH at 25 ° C. was adjusted to 5.0 to obtain staining solution 1.

Comparative Preparation Example 1 (Preparation of Comparative Staining Solution 1)
Comparative staining solution 1 was obtained in the same manner as in Preparation Example 1 except that isopropyl alcohol was not added.

Comparative Preparation Example 2 (Preparation of Comparative Staining Solution 2)
After mixing 1.0 g of metal-containing dye “Kayakalan Bordeaux BL” (manufactured by Nippon Kayaku Co., Ltd.) and 30.0 g of isopropyl alcohol which is an amphiphilic solvent, the pH at 25 ° C. is adjusted to 2.5 using acetic acid. It was adjusted. Water was added to this solution to make the total volume 240 mL, and a comparative staining solution 2 was obtained.

Comparative Preparation Example 3 (Preparation of Comparative Staining Solution 3)
After mixing 1.0 g of metal-containing dye “Kayakalan Bordeaux BL” (manufactured by Nippon Kayaku Co., Ltd.) and 30.0 g of isopropyl alcohol which is an amphiphilic solvent, the pH at 25 ° C. is adjusted to 7.0 using acetic acid. It was adjusted. Water was added to this solution to make the total volume 240 mL, and a comparative staining solution 3 was obtained.

Comparative Preparation Example 4 (Preparation of Comparative Staining Solution 4)
Comparative dyeing solution in the same manner as in Preparation Example 1, except that instead of the metal-containing dye “Kayakalan Bordeaux BL”, a disperse dye “Kayalon Microester Blue AQ-LE” (manufactured by Nippon Kayaku Co., Ltd.) was used. 4 was obtained.

Comparative Preparation Example 5 (Preparation of Comparative Staining Solution 5)
Comparative staining solution 5 was obtained in the same manner as in Preparation Example 1, except that o-dichlorobenzene was used instead of isopropyl alcohol.

Example 1 (Production of dyed plastic lens 1)
A commercially available plastic lens “Phoenix” (manufactured by HOYA Corporation, material: polyurea resin, center wall thickness: 2.0 mm, transmittance at a wavelength of 550 nm before dyeing: 90.4%) prepared in Preparation 1 Was dyed in an autoclave at a temperature of 115 ° C. and a pressure of 1.13 MPa for 20 minutes to obtain a dyed plastic lens 1. The evaluation results are shown in Table 1. The dyed plastic lens obtained by the manufacturing method of Example 1 showed good results in all of the dyeing density, dyeing uniformity, and weather resistance. In addition, no lens deformation occurred before and after dyeing.

Example 2 (Production of dyed plastic lens 2)
Commercially available plastic lens “EYAS” (manufactured by HOYA Co., Ltd., material: polythiourethane resin, center wall thickness: 2.0 mm, transmittance at a wavelength of 550 nm before dyeing; 90.7; dyeing solution 1 prepared in Preparation Example 1 %), And the others were the same as in Example 1 to obtain a dyed plastic lens 2. The evaluation results are shown in Table 1. The dyed plastic lens obtained by the production method of Example 2 showed good results in all of the dyeing density, dyeing uniformity, and weather resistance. In addition, no lens deformation occurred before and after dyeing.

Comparative Example 1 (Production of comparatively dyed plastic lens 1)
Using the dyeing solution 1 prepared in Preparation Example 1, dyeing was performed for 20 minutes at a temperature of 85 ° C. and atmospheric pressure to obtain a comparatively dyed plastic lens 1. The evaluation results are shown in Table 1. Plastic lenses were not dyed because they were dyed under temperature and pressure conditions outside the scope of the present invention.

Comparative Example 2 (Production of Comparative Dyeing Plastic Lens 2)
A comparative dyed plastic lens 2 was obtained in the same manner as in Example 1 except that the comparative dyeing solution 1 prepared in Comparative Preparation Example 1 was used. The evaluation results are shown in Table 1. Since it dye | stained with the comparative dyeing liquid 1 which does not contain an amphiphilic solvent, the plastic lens was not dye | stained.

Comparative Example 3 (Production of comparatively dyed plastic lens 3)
A comparative dyed plastic lens 3 was obtained in the same manner as in Example 1 except that the comparative dyeing solution 2 prepared in Comparative Preparation Example 2 was used. The evaluation results are shown in Table 1. Since the dye was stained with the comparative staining solution 2 having a pH of less than 3.0 at 25 ° C., the plastic lens was only stained at a low density.

Comparative Example 4 (Production of Comparative Dyeing Plastic Lens 4)
A comparative dyed plastic lens 4 was obtained in the same manner as in Example 1 except that the comparative dyeing solution 3 prepared in Comparative Preparation Example 3 was used. The evaluation results are shown in Table 1. The plastic lens was stained only at a low density because it was stained with the comparative staining solution 3 having a pH at 25 ° C. exceeding 6.5.

Comparative Example 5 (Manufacture of Comparative Dyeing Plastic Lens 5)
A comparatively stained plastic lens 5 was obtained in the same manner as in Example 1 except that the dyeing was performed at a temperature of 85 ° C. The evaluation results are shown in Table 1. Since the dyeing was performed at a temperature of less than 90 ° C., the plastic lens was dyed only at a low density.

Comparative Example 6 (Production of comparatively dyed plastic lens 6)
A comparatively stained plastic lens 6 was obtained in the same manner as in Example 1 except that the dyeing was performed at a temperature of 145 ° C. The evaluation results are shown in Table 1. Since the dyeing was performed at a temperature exceeding 140 ° C., the plastic lens was deformed.

Comparative Example 7 (Production of comparative dyeing plastic lens 7)
A comparatively stained plastic lens 7 was obtained in the same manner as in Example 1 except that it was dyed at a pressure of 0.43 MPa. The evaluation results are shown in Table 1. The plastic lens was not dyed because it was dyed at a pressure of less than 0.5 MPa.

Comparative Example 8 (Production of Comparative Dyeing Plastic Lens 8)
A comparatively dyed plastic lens 8 was obtained in the same manner as in Example 1 except that it was dyed at a pressure of 5.13 MPa. The evaluation results are shown in Table 1. Since the dyeing was performed at a pressure exceeding 5.0 MPa, the plastic lens was deformed.

Comparative Example 9 (Production of Comparative Dyeing Plastic Lens 9)
A comparatively stained plastic lens 9 was obtained in the same manner as in Example 1 except that the comparative dyeing solution 4 prepared in Comparative Preparation Example 4 was used. The evaluation results are shown in Table 1. Plastic lenses dyed with disperse dyes instead of metal-containing dyes could not be dyed uniformly and had poor weather resistance.

Comparative Example 10 (Production of Comparative Dyeing Plastic Lens 10)
A comparative dyed plastic lens 10 was obtained in the same manner as in Example 1 except that the comparative dyeing solution 5 prepared in Comparative Preparation Example 5 was used. The evaluation results are shown in Table 1. When o-dichlorobenzene was used as a carrier instead of the amphiphilic solvent, the surface of the plastic lens was roughened and uniform dyeing could not be achieved.

  According to the method for producing a dyed plastic lens of the present invention, it is possible to uniformly dye a plastic lens using a metal-containing dye, and it can be used for spectacle lenses, camera lenses, projector lenses, telescope lenses, magnifier lenses, A dyed plastic lens that is suitably used and has excellent weather resistance can be produced.

Claims (4)

  A dyeing solution containing a metal-containing dye, an amphiphilic solvent, and water and having a pH of 3.0 to 6.5 at 25 ° C. and a plastic lens are brought into contact with each other, and a temperature of 90 to 140 ° C. and a pressure of 0.5 to A method for producing a dyed plastic lens, which is dyed under a condition of 5.0 MPa.   The method for producing a dyed plastic lens according to claim 1, wherein at least one of the amphiphilic solvents is an alcohol having 1 to 7 carbon atoms.   The said plastic lens has a functional group which can form a chemical bond with the metal in the said metal-containing dye, and this functional group is at least 1 sort (s) chosen from an amino group and a carboxyl group. The manufacturing method of the dyeing | staining plastic lens of description.   The dyed plastic lens obtained by the manufacturing method in any one of Claims 1-3.