KR100649348B1 - Dyeing method of photochromic spectacles lens - Google Patents

Abstract

A glasses lens dyeing method adopting photochromic is provided to reduce defective of the lens, when the lens is subjected to a dyeing process, by directly dyeing the glasses lens. A dyeing solution consisting of photochromic compound, ultraviolet absorption agent, organic solvent, and surfactant is prepared. The dyeing solution is stirred in water of 100 wt% at a temperature of 60 to 120 deg.C in order to form aqueous dyeing solution. A glasses lens is immersed in the aqueous dyeing solution for 30 to 120 minutes. The photochromic compound is a naphtopyran based compound.

Description

Dyeing method of photochromic spectacles lens

The present invention relates to a method for dyeing spectacle lenses into which photo-compatible photochromic is introduced, and more particularly, forming a aqueous dyeing solution by dissolving a dye solution containing a photo-compatible photochromic compound and an ultraviolet absorber in water and then molding It relates to a method of immersing one spectacle lens as it is.

In general, there are various methods known to dye plastic eyeglass lenses, but they have the following problems.

That is, when the dyeing is performed using a disperse dye using water as a dispersion medium, it is difficult to apply to a thermoplastic resin lens having a low glass transition temperature because the dyeing is performed at a relatively high temperature. In carrier dyeing, thermoplastic resins are inferior in solvent resistance as compared with thermosetting resins. Therefore, in the carrier agent generally used in the optical plastic lens, there is a tendency that the lens surface is invaded and the transparency is lost.

Moreover, the conventional carrier contains trichlorobenzene, dichlorobenzene, phenylphenol, diphenyl, methylnaphthalene, etc. as a main component. These compounds are mentioned as a substance which concerns about environmental pollution and the bad effect to a human body. Therefore, in consideration of environmental problems, it is not preferable to use a carrier agent containing these compounds as a main component in the future.

In the case of pressure dyeing, there is a possibility that the optical performance as a plastic lens may be lost by pressurization, and in the method of heating and subliming the organic dye in the gas phase to color, in general, the thermoplastic resin is inferior in heat resistance, so this method is applied. It's hard to do

In hard coat film dyeing, since it is difficult to contain a large amount of dye in a hard film, high concentration dyeing is difficult. In addition, when the film thickness is made thick to contain a large amount of dye, cracks tend to enter the hard coat film, the shape of the lens is distorted, and the film hardness is weakened. Moreover, there also exists a problem that light resistance is bad compared with the case of dyeing directly on a base material.

In the method of dissolving and polymerizing a dye in a raw material of a plastic lens base material, the colored concentration of the formed lens depends on the thickness of the lens. For example, in a concave lens in which the central portion of the lens is thinner than the peripheral portion, the color of the central portion is light and the peripheral portion is dark. Therefore, there is a possibility that the tints of colors are different from each other in the entire lens.

On the other hand, in the case of manufacturing a color changing lens is generally a method of injecting a color change drug and dye before casting for the molding of the spectacle lens. In the case of the above method, since the material of the spectacle lens is denatured, there is a problem that the defect rate is considerably high. In addition, it is pointed out that when rimless processing, the introduction of a color change lens is easily broken or broken.

In addition, in spite of many techniques for the color fading lens as described above, no color fading lens imparted UV blocking function to the color fading lens.

The inventors of the present invention solve the problem of the conventional dyeing method of the spectacle lens, can be dyed by a simple method, and researched to find a dyeing method of the spectacle lens introduced at the same time UV protection function and fashion.

As a result, a method of aqueousizing a dye solution containing a photocompatible photochromic compound and an ultraviolet absorber and immersing a previously formed spectacle lens was developed.

According to the present invention, unlike the spectacle lens in which the existing photochromic compound is introduced, since the dye is directly applied to the surface, the defect rate occurring during the casting process can be improved, and the physical properties of the spectacle lens before dyeing can be maintained as it is. Breakage can be significantly reduced.

In addition, the spectacle lens manufactured according to the present invention is characterized in that the color is changed from colorless to ultraviolet in the case of indoors, colorless to colored, or discoloration can also be changed from colored to colored and other products due to the variety of colors It is excellent in differentiation, and is excellent in other glare prevention, durability, and UV protection rate.

Accordingly, an object of the present invention is to provide a method of dyeing spectacle lenses into which photo-compatible photochromic is introduced.

In addition, the present invention includes a spectacle lens introduced with a photo-compatible photochromic compound having excellent UV resistance and durability and fashion.

The present invention provides a dyeing solution (A) comprising 1) 0.01 to 1 part by weight of the photocompatible photochromic compound, 0.01 to 1 part by weight of an ultraviolet absorber, 1 to 10 parts by weight of an organic solvent and 1 to 10 parts by weight of a surfactant. Step 2) preparing an aqueous dyeing solution (B) by stirring 2 to 20 parts by weight of the dyeing solution (A) at a temperature of 60 ~ 100 ℃ to 100 parts by weight of water, and 3) the aqueous dyeing solution The spectacle lens dyeing method is characterized by the introduction of a photo-compatible photochromic method comprising the step of immersing and dyeing the spectacle lens molded in (B) for 30 to 120 minutes.

The present invention also includes a spectacle lens cast on the surface of the photo-compatible photochromic prepared by the above method.

Hereinafter, the present invention will be described in detail.

The present invention is prepared by dissolving a dyeing solution containing a photo-compatible photochromic compound and an ultraviolet absorber in water to prepare an aqueous dyeing solution, and then immersed and dyed the formed spectacle lens as it is. Unlike the lens, it can be dyed directly on the surface to improve the defective rate during the casting process, and can maintain the physical properties of the spectacle lens before dyeing, which can greatly reduce the damage of the spectacle lens. In this case, it is characterized by the change in color, and it can be changed from colorless to colored, or from colored to colored, so it is excellent in differentiation from other products due to the variety of colors, and is excellent in anti-glare, durability, and UV blocking rate. A spectacle lens in which photochromic is introduced can be manufactured.

Hereinafter, the spectacle lens dyeing method in which the photocompatible photochromic of the present invention is introduced will be described in detail.

Step 1) is a step of preparing a dyeing solution (A) comprising 0.01 to 1 part by weight of the photocompatible photochromic compound, 0.01 to 1 part by weight of the ultraviolet absorber, 1 to 10 parts by weight of the organic solvent and 1 to 10 parts by weight of the surfactant. to be.

The photocompatible photochromic compound refers to a compound that exhibits photochromism or photochromism, and refers to a compound that changes from colorless to colored by color reaction to colored to colored.

When the compound is irradiated with light of a specific wavelength in solution or solid state, the chemical structure is changed, and thus the absorption spectrum is changed. However, when the compound is irradiated with light of a different wavelength or left in a dark place, the compound returns to the beginning.

Specific examples of the above-described photocompatible photochromic compounds include silver halides and the like as inorganic compounds, and there are many types of organic compounds, but isomerization of double bonds (azobenzene and thioindigo), hydrogen, depending on the reaction mode. Based on compatibility by migration (salicylidene aniline), by pericyclic reactions (purgid), by causing cyclic addition reactions (anthracene), by indicating bound ion series (triphenylmethane and spiropyrane) There is this.

In the present invention, all of the above-described compounds may be used as the photocompatible photochromic compound, but it is particularly preferable to use naphthopyran compounds. Such photochromic compounds are processed in a neutral state that can be used in a neutral solvent in the art, or processed in an aqueous state for use in an aqueous solvent, or are provided in a powder form (oil-based) as it is, and in the present invention, a powder form is used. It is desirable to.

The amount of the photo-compatible photochromic compound is 0.01 to 1 part by weight, and when the amount is less than 0.01 part by weight, it is difficult to realize the color of the photochromic compound. Is saturated and not dyed.

The ultraviolet absorber may be a formamidine-based UV absorber, a polymer Hals-based UV absorber or a mixture thereof.

The formamidine-based ultraviolet absorber may be used including a compound represented by the following formula (1).

[Formula 1]

The polymer Halus ultraviolet absorber 1,3.5-triazine-2,4,6-triamine (1,3.5-Triazine-2,4,6-triamine,), N, N '' '-[1,2 -Ethane-diyl-bis [[[4,6-bis- [butyl (1,2,2,6,6-pentamethyl-4-piperidinyl) amino] -1,3,5-triazine-2 -Yl] imino] -3,1-propanediyl]]-bis- [N ', N "-dibutyl-N', N" -bis (1,2,2,6,6-penta) Methyl-4-piperidinyl (N '' '-[1,2-ethane-diyl-bis [[[4,6-bis- [butyl (1,2,2,6,6-pentamethyl-4-piperidinyl ) amino] -1,3,5-triazine-2-yl] imino] -3,1-propanediyl]]-bis- [N ', N' '-dibutyl-N', N ''-bis (1, 2,2,6,6-pentamethyl-4-piperidinyl) may be used, and the molecular weight of the polymer is preferably in the range of 2,000 to 4,000.

The amount of the ultraviolet absorber is 0.01 to 1 parts by weight, and when the amount of the ultraviolet absorber is less than 0.01 parts by weight or more than 1 part by weight, the durability (points of discoloration when exposed to ultraviolet rays) decreases depending on the type of the photocompatible pigment. have.

      The organic solvent may be used one or a mixture of two or more selected from methylene chloride, chloroform and methyl ethyl ketone, the amount of use is in the range of 1 to 10 parts by weight, when the amount is less than 1 part by weight of the solution of the photochromic compound It is difficult to paint, and if it exceeds 10 parts by weight, it may change the physical properties of the lens surface.

As the organic solvent, it is more preferable that the organic solvent is a mixture of 1 to 3 parts by weight of methylene chloride, 1 to 3 parts by weight of chloroform and 1 to 4 parts by weight of methyl ethyl ketone.

The surfactant may be one or a mixture of two or more selected from nonionic surfactants and anionic surfactants. The nonionic surfactants may be propylene glycol, amine oxide, polyoxyethylene ether, ethylene glycol, fatty acid amide, or the like. One kind or a mixture of two or more kinds selected from can be used.

The anionic surfactant may be used one or a mixture of two or more selected from alpha olefins, alkyl sulfonates, alkyl sulfates and alkyl phosphoric acid salts.

The amount of the surfactant is 1 to 10 parts by weight, and if the amount of the surfactant is less than 1 part by weight, it is impossible to mix the organic material and the water. When the amount of the surfactant is more than 10 parts by weight, the physical properties of the dye may be changed on the lens surface. .

Step 2) is a step of preparing an aqueous dyeing solution (B) by stirring 1 to 10 parts by weight of the dyeing solution (A) to 60 ~ 100 ℃ temperature conditions with respect to 100 parts by weight of water.

At this time, when the amount of the dyeing solution (A) is less than 1 part by weight or more than 10 parts by weight, the dispersibility of the lens surface may be weak or physical properties may be changed on the lens surface. If it exceeds 100 ℃, it gives a change in the physical properties of the lens.

Step 3) is a step of dyeing by dipping for 30 to 120 minutes the spectacle lens molded in the aqueous dye solution (B).

The molded spectacle lens may be made of a polymer resin selected from polymethyl methacrylate and polycarbonate, and may be particularly preferable when the spectacle lens is made of polymethyl methacrylate.

As described above, the spectacle lens dyed by the method of the present invention and coated on the surface of the photo-compatible photochromic finishes the discoloration within 2 to 3 minutes after various colors and fast discoloration speed discoloration, thereby reliably obscuring the dark and dark disadvantages of the existing discoloration lens. It can be improved.

In addition, when processing rimless glasses, it is not easily broken or broken as compared to conventional color changing lenses, so it is possible to process any type of spectacle frames without any difficulty. It can maintain the sun protection even afterwards, protecting the eyes from harmful rays.

In addition, unlike the existing discoloration lens, which is difficult to wear due to deterioration of the lens or change of the color itself when exposed to long-term sun exposure or wear for a long time, it has excellent durability in discoloring function and maintenance.

Hereinafter, the present invention will be described in detail with reference to Examples, but the present invention is not limited by the following Examples.

Example 1 Preparation of Staining Solution

2 parts by weight of methylene chloride as an organic solvent, 1 part by weight of chloroform, 2 parts by weight of methyl ethyl ketone, and 0.1 parts by weight of naphthopyran compound as a photochromic compound are added thereto, and 0.05 parts by weight of formamidine-based ultraviolet absorber and polymer Hals ( A dyeing solution (A) containing 0.05 parts by weight of a HALS) ultraviolet absorber, 2 parts by weight of propylene glycol as a surfactant, 1 part by weight of an alpha olefin, and 2 parts by weight of an amine oxide was prepared.

10 parts by weight of the dye solution (A) was mixed with 100 parts by weight of water, and stirred at about 90 ° C. to prepare an aqueous dye solution (B).

Example 2 Dyeing of Spectacle Lenses

The preformed spectacle lens of polymethyl methacrylate (PMMA) material is immersed in 100 parts by weight of the aqueous dyeing solution (B) prepared in Example 1 and then dyed for about 50 minutes and dried to obtain the present invention. The spectacle lens into which the photocompatible photochromic compound was introduced was prepared.

Experimental Example

The UV blocking effect of the spectacle lens manufactured by Example 2 was measured using a UV meter (ultraviolet B section), and as a result, an effect of blocking at least 80% was confirmed.

In addition, the discoloration rate was measured by direct exposure to sunlight, and as a result, the recovery rate after 10 minutes was confirmed to be within 1 minute.

As described above, according to the present invention, unlike conventional dyeing lenses can be directly dyed to the molded spectacle lens to reduce the defective rate (30 ~ 40% improvement) occurring in the dyeing process, and The physical properties can be kept intact, and the damage of the spectacle lens can be greatly reduced.

In addition, it is excellent in differentiation from other products due to the variety of colors, and also excellent in preventing glare, durability, and UV protection.

In addition, indoors can remain colorless and change to colored when exposed to ultraviolet light or from colored to colored.

You can also judge the darkness and blur of the color according to the intensity of ultraviolet rays. Due to the various colors, not only the design aspect, but also the production cost reduction and improvement of the parts dependent on imports can be improved compared to the existing photochromic sunglass, and this can be effective as a functional item in the shrunk spectacle lens industry. It is also effective for refraction.

Claims (13)

delete 1) preparing a dyeing solution (A) comprising a photo-compatible photochromic compound, an ultraviolet absorber, an organic solvent and a surfactant, 2) preparing an aqueous dyeing solution (B) by stirring the dyeing solution (A) at a temperature condition of 60 ~ 100 ℃ with respect to 100 parts by weight of water, and 3) comprising the step of immersing the spectacle lens molded in the aqueous dye solution (B) for 30 to 120 minutes, the dyeing, The optically compatible photochromic compound is a naphthopyran-based compound, characterized in that the optical lens photochromic introduced dye lens method. The method of claim 2, The ultraviolet absorber is a formamide-based UV absorber, a polymer Hals-based UV absorber or a mixture of the optical compatibility photochromic introduced, characterized in that a mixture thereof. The method of claim 3, wherein The method of dyeing spectacle lenses, wherein the formamidine-based ultraviolet absorbents include a compound represented by Formula 1 below: [Formula 1]

The method of claim 4, wherein The polymer Halus ultraviolet absorber 1,3.5-triazine-2,4,6-triamine (1,3.5-Triazine-2,4,6-triamine,), N, N '' '-[1,2 -Ethane-diyl-bis [[[4,6-bis- [butyl (1,2,2,6,6-pentamethyl-4-piperidinyl) amino] -1,3,5-triazine-2 -Yl] imino] -3,1-propanediyl]]-bis- [N ', N "-dibutyl-N', N" -bis (1,2,2,6,6-pentamethyl 4-piperidinyl (N '' '-[1,2-ethane-diyl-bis [[[4,6-bis- [butyl (1,2,2,6,6-pentamethyl -4-piperidinyl) amino] -1,3,5-triazine-2-yl] imino] -3,1-propanediyl]]-bis- [N ', N' '-dibutyl-N', N ''-bis (1,2 , 2,6,6-pentamethyl-4-piperidinyl), wherein the spectacle lens dyeing method introduced photo-compatible photochromic. The method of claim 5, The organic solvent is a spectacle lens dye-introduced method of photo-compatible photochromic introduced, characterized in that one or two or more selected from methylene chloride, chloroform and methyl ethyl ketone. The dyeing solution (A) according to any one of claims 2 to 6, wherein 0.01 to 1 part by weight of the photocompatible photochromic compound, 0.01 to 1 part by weight of an ultraviolet absorber, 1 to 10 parts by weight of an organic solvent and The spectacle lens dyeing method of the photo-compatible photochromic introduced, characterized in that contained in 1 to 10 parts by weight of the surfactant. The method of claim 7, wherein The organic solvent is a spectacle lens dyeing method, characterized in that a mixture of 1 to 3 parts by weight of methylene chloride, 1 to 3 parts by weight of chloroform and 1 to 4 parts by weight of methyl ethyl ketone. The method of claim 8, The surfactant is a spectacle lens dyeing method introduced photo-compatible photochromic, characterized in that the mixture of one or two or more selected from nonionic surfactants and anionic. The method of claim 9, The nonionic surfactant is a photolensyl dye-induced spectacle lens, characterized in that the propylene glycol, amine oxide, polyoxyethylene ether, ethylene glycol and fatty acid amide selected from the group consisting of one or two or more. The method of claim 9, The anionic surfactant is a spectacle lens dyeing method introduced photo-compatible photochromic, characterized in that one or a mixture of two or more selected from alpha olefins, alkyl sulfonates, alkyl sulfates and alkyl phosphates. The method of claim 7, wherein The molded spectacle lens dyeing method of the optical compatibility photochromic introduced, characterized in that the polymethyl methacrylate polymer resin material. As prepared by any one of claims 2 to 6, The spectacle lens, wherein the photo-compatible photochromic is dyed on the surface.