KR20110088900A - Composition of coating materials for clolr changeable lense to the light and coating method using the same - Google Patents

Abstract

PURPOSE: A photochromic hard coating composition is provided to ensure excellent lightness, moldability, dyeability, and transparency and to enable the hardcoating enhancing impact resistance, durability and discoloration effects. CONSTITUTION: A photochromic hard coating composition comprises the urethane composition of a polyurethane prepolymer having a polyisocyanate terminal, polyol, polyol composition, polyvinylbutyral resin, photochromic dye, catalyst, and other additives. A coating method for the hard coating liquid comprises the steps of: applying the hard coating liquid on the surface of the lens; curing the coating lens to form a film; applying general hard coating liquid to the hardened film; and hardening the surface of the lenses to form a film.

Description

Photochromic hard coating solution composition for polycarbonate and general lens and coating method using same {{COMPOSITION OF COATING MATERIALS FOR CLOLR CHANGEABLE LENSE TO THE LIGHT AND COATING METHOD USING THE SAME}

The present invention is a coating liquid for coating for adhesion and discoloration of polycarbonate (PC) and general lenses, and a coating method using the same, a urethane composition of a polyisocyanate-terminated polyurethane prepolymer, polyol, epoxy composition, polyvinyl buty Consists of ral resins, photochromic dyes, catalysts and other additives. The present invention relates to a hard coating solution composition for photochromic lenses, which can produce photochromic products using polyurethane urethane compositions and polyols. The present invention relates to a coating liquid composition capable of hard coating with high impact resistance, durability and discoloration effect while having optical properties such as light weight, moldability, dyeing property and transparency of a lens.

As the number of people wearing glasses increases in modern times, interest in eyes has been increasing. For this reason, eye protection products such as sunglasses, fashion lenses, over-the-counter and prescription lenses, safety guards and goggles, which are transparent plasticine products that provide good image quality while reducing incident light to the eyes, are needed and used in various applications. . The need for these various applications has led to an interest in photochromic plastic products used for optical applications, and in particular, eye photochromic plastic lenses have received a lot of attention due to the weight advantages they offer compared to glass lenses. come.

Photochromicity also refers to a phenomenon involving reversible color change that occurs when an organic or inorganic material, or a product containing such materials, is exposed to ultraviolet light. The radiation sources contained by ultraviolet light include all light from the light of sunlight and mercury lamps. When the photochromic material is exposed to ultraviolet light, it shows color change, and when the ultraviolet light is blocked, the photochromic material returns to its original color or colorless state. Products containing this photochromic material exhibit color changes, resulting in reversible light transmission changes.

As described above, the lens of the color changing method by the ultraviolet light is differently referred to as a dimming lens. Most photochromic lenses on the market are manufactured by casting in a mold by mixing polymers and photochromic dyes. Photochromic dyes had to secure internal space to generate structural changes when UV light was irradiated. However, when high density resin is used, it is difficult to secure space. Therefore, there are many limitations to increase the strength and scratch resistance of the coated film. This exists. Current photochromic compounds are 1,3,3-trimethyl-indolinobenzospiropy. Later, various photochromic compounds were introduced to complement this compound, and are typically spirooxazine compounds. At present, the lens produced by mixing photochromic compound and monomer into a mold mold and hardening thereof has low strength and difficulty in manufacturing a high refractive index lens, which makes it difficult to produce lenses of various materials. The lens produced by the casting method has to secure a space for the photochromic dye to act, there is a problem that the strength of the lens itself is weakened, there was a problem that the thickness of the lens can not be made thinner than a certain.

FIG. 1 schematically shows a layer of a lens manufactured by a general coating method, and has a total of four layers of a hard coating layer, a coloring layer, a multi-coating layer, and a functional coating layer. One layer is a coating layer for protecting the lens with a hard coating layer. The second layer is a coloring layer for imparting various colors of the lens, and the coloring layer contains a photochromic dye. The third layer is a multi-coating layer that removes the reflection of light, and the fourth layer consists of a functional coating layer that improves the functionality by adding the functionality of the lens. This is impossible. Therefore, when coating with hard solution developed by this time, only multi-coating after hard coating including discoloration dye on general lens is completed, and considering the production cost and quality, it is superior to the existing method when producing with this coating method. By using the general lens of the lens itself was also excellent in intensity and discoloration characteristics.

However, in the manufacture of discolored lenses by dissolving photochromic dyes with commonly used hard coating solutions, polar materials could not be used due to electrical properties. Therefore, the lenses prepared by the conventional coating method has a problem of adhesion of the coating film, the use of the polyacrylic resin of the coating film was not good because the strength of the coating film was not possible to manufacture a photochromic coating lens.

Among the existing materials, the photochromic lens is easy to manufacture and has good chemical and thermal stability, but it is difficult to diversify into the material, and the center thickness of the lens should be 2mm or more and the thickness deviation with the variable is severe. The difference in chromaticity was severe and there were many visual problems.

The present invention has been made to solve the above problems, it is possible to produce a photochromic product using a polyol and a urethane composition of a polyisocyanate terminated polyurethane prepolymer, the light weight, moldability, An object of the present invention is to provide a coating liquid composition capable of hard coating which has optical properties such as dyeability, transparency, and high impact resistance, durability and discoloration effect.

In addition, photochromic dyes can be mixed-coated in hard coatings, thereby reducing the four coating layers into two layers, thereby improving the productivity of lens products and changing the binder to simplify the manufacturing process. It is an object of the present invention to provide a coating liquid which provides a composition, enhances the efficiency of discoloring effect of the coating, and enhances the adhesion of the coating liquid to the lens.

The present invention relates to a photochromic hard coating liquid composition for polycarbonate and a general lens and a coating method using the same. In the coating liquid for coating for adhesion and discoloration of a photochromic lens, the urethane of a polyurethane prepolymer of a polyisocyanate terminal And a composition, a polyol, an epoxy composition, a polyvinyl butyral resin, a photochromic dye, a catalyst and other additives.

Further, 20 to 40% by weight of the urethane composition of the polyisocyanate terminated polyurethane prepolymer, 20 to 60% by weight of polyol, 2 to 8% by weight of epoxy composition, 1 to 5% by weight of polyvinyl butyral resin, and 0.04 to photochromic dye 0.08% by weight, 0.1-0.5% by weight of catalyst and 0.1-35% by weight of other additives.

In addition, the first step of coating the hard coating solution of the photochromic lens on the surface of the lens; Curing the lens coated with the coating solution at 85 ° C. or lower for 3 to 4 minutes to form a film; Second coating the cured film with a general hard coating solution; Forming a film by curing the surface of the secondary coated lens at 75 to 85 ° C. for 3 to 4 minutes and curing (moistening) at 120 ° C. for 90 to 120 minutes; It is done.

The present invention can produce a photochromic product using a polyurethane composition and a polyol of the polyurethane prepolymer of the polyisocyanate terminal, and has an optical resistance such as light weight, moldability, dyeability, transparency of the lens, and impact resistance. It is possible to provide a coating liquid composition capable of hard coating with improved performance and durability and discoloration effect. By reducing the existing lens coating layer into two layers, it is possible to change the refractive index by changing the binder to simplify the production of technical problems for improving the productivity of the lens products and the simple manufacturing process. It is effective in providing a coating liquid composition applicable to the lens of the present invention, increasing the efficiency of discoloration effect of the coating, and improving the adhesion of the coating liquid to lenses such as polycarbonate that are difficult to attach.

1 is a view schematically showing a coating layer of a conventional lens.
Figure 2 schematically shows the structural change of the photochromic dye contained in the photochromic hard coating liquid composition according to the present invention.
Figure 3 schematically shows a coating layer of a lens coated with a photochromic hard coating solution composition according to the present invention.

Hereinafter, a photochromic hard coating solution composition (hereinafter, a coating solution composition) for a polycarbonate and a general lens according to the present invention will be described in detail.

First, the coating liquid composition according to the present invention is a mixture of a urethane composition, a polyol, an epoxy composition, a polyvinyl butyral resin, a photochromic dye, a catalyst and other additives of a polyurethane prepolymer of a polyisocyanate terminal.

The present invention is a coating liquid composition which can be coated on the surface of a spectacle lens composed of a general spectacle lens and a polycarbonate having a somewhat low adhesion, the spectacle lens composed of an organic polymer material having a relatively high adhesion than a polycarbonate is composed of a photochromic lens To do it.

The preferred amount of the coating liquid composition according to the present invention is 20 to 40% by weight of the urethane composition of the polyisocyanate terminated polyurethane prepolymer, 20 to 60% by weight of the polyol, 2 to 8% by weight of the epoxy composition, and 1 to 5 polyvinyl butyral resins. Weight%, photochromic dye 0.04-0.08 weight%, catalyst 0.1-0.5 weight% and other additives 0.1-35 weight%.

The urethane composition and the polyol of the polyurethane prepolymer of the polyisocyanate terminal determine the impact strength and the heat resistance of the lens coated with the coating liquid composition as the main raw material of the coating liquid composition. The coating liquid composition which can comprise a male lens can be formed.

The urethane composition (NCO-PRP) of a polyisocyanate terminated polyurethane prepolymer is a compound containing two or more NCO groups in a molecule obtained by reacting an excess polyisocyanate with a polyol.

The ratio of NCO group and OH group is 2: 1 to 4: 1 so that the NCO group remains at the end of the polymer and the molecular weight (Mn) is 1500 to 4000.

As a main raw material of the coating liquid composition, it is an additive having excellent optical properties such as impact resistance, abrasion resistance, and scratch resistance.

The urethane composition of the polyisocyanate-terminated polyurethane prepolymer is composed of one selected from HMDI Isocyanurate Trimer, HMDI Uretidione Dimer, and HMDI Biuret Trimer.

HMDI is a block copolymer as 4.4-methylenebis (cyclohexylisocyanate).

HMDI Isocyanurate Trimer has a rigid property, and the chemical structure at its end is configured as follows. The three ends of the chemical structure have NCO groups, which have excellent durability and mechanical properties, and are excellent in cost compared to excellent performance.

HMDI Uretidione Dimer has a rigid property, and the chemical structure at the end thereof is configured as follows. The two ends of the chemical structure have NCO groups, which have excellent durability and mechanical properties, and are excellent in cost compared to excellent performance.

HMDI Biuret Trimer has strong characteristics, and its chemical structure is composed as follows. The three ends of the chemical structure have NCO groups, so it has excellent durability and weather resistance.

Polyol is made of dicarboxylic acid and polyhydric alcohol, excellent molecular weight (Mn) of 50 ~ 6000, and provides the efficiency of reversible photochromic by securing the free space of the photochromic dye.

The polyol was composed by mixing at least one of polyester polyol, polyether polyol, and polycapolactone polyol, and the chemical structural formula of each polyol is shown below.

Epoxy composition to improve the adhesion of the coating liquid composition to the spectacle lens by using Diglycidly Ether of Bisphenol-A excellent in moisture resistance chemical resistance, the chemical structural formula according to it is shown as follows.

Polyvinyl butyral resin (PVB) improves the adhesion of the coating liquid composition to a lens composed of a general spectacle lens and a low adhesion polycarbonate such as the epoxy composition.

Photochromic dyes include a photochromic compound composed of spirorin, spiroxazine, and azo compounds in the coating solution, and are transparent. However, when exposed to ultraviolet light, the color of the photochromic compound changes its molecular form, resulting in a colored state.

That is, the variable color of photochromic color can be designated by mixing one or more dyes containing said photochromic compound.

Figure 2 schematically shows the structural change of the photochromic dye, the structural change of the photochromic dye is exposed to ultraviolet light, the portion of the normal structure is bound by the ionizer breaks the coloration state appears to require sufficient space to change the structure Done.

If the space of the structural change of the photochromic dye is insufficient, it is necessary to ensure sufficient space for the structural change of the dye because the structure can be changed by ultraviolet rays and affect other external spaces.

Therefore, in the present invention, in the structural change of the photochromic dye, photochromic containing a photochromic compound composed of spiropyran (SP), spirooxazine (SO) and azo compounds which can secure sufficient space Use dyes.

Photochromic dyes containing photochromic compounds consisting of spirorin, spirochete and azo compounds include Rush yellow, Corn yellow, Ruby, Berry red, Oxford blue, Volcanic grey, Midnight grey, Solar yellow, Graphite, etc. In addition, one or more colors may be selected and mixed according to the purpose and characteristics thereof, but the variable color of photochromism may be designated by adjusting the amount of color added within the range of the total amount of photochromic dye.

Spiropyran (SP) and spirooxazine (SO) fix photochromic substances contained in photochromic dyes. When the molecules of photochromic substance are exposed to ultraviolet rays, CO bonds are broken and the coloring structure of isomers When exposed to visible light or heat, the broken CO is combined to return to its original color.

However, when photochromic dye molecules are exposed to ultraviolet rays for a long time, photolysis occurs and photochromic properties are lost. The photochromic dye material immobilized on the matrix is slower than photoimmobilized on the polymer matrix, and the matrix itself is polymer. Compared to the photochemical stability against ultraviolet rays is excellent. In particular, when the photochromic molecule naphthopyran (NP) is immobilized on the matrix, the environment of the matrix is highly dependent on the photostability. Due to the attraction between the matrix, the photochromic molecules are stabilized in polar form, resulting in a slow discoloration rate.

In other words, when a hydrophobic matrix without OH groups is used, OH groups on the surface form strong bonds, thereby minimizing dye movement, resulting in fast discoloration rate and high light stability.

Catalysts include Tinoctylate, Stannous octoate, Dibutyltin dichloride (DBTDC), Dibutyltin dilaurate (DBTDL), 1,4-diazabicyclo [2,2,2] octane (1, One or more of 4-Diazabicyclo [2,2,2] octane, DABCO) can be selected and used, and the amount added is adjusted according to the characteristics of the added catalyst within the total amount of addition.

The above catalysts have characteristics as curing accelerators as reaction indicators.

Other additives include a pinol inhibitor including a solvent and an antioxidant or an ultraviolet stabilizer. The additive is added as necessary to facilitate the mixing of the additive including the urethane composition and to form a stable coating solution in ultraviolet light.

The solvent is made of MetyhlEthyl Ketone, Toluene, and Ethylene Glycol Monomethyl Ether (MCS) to facilitate dissolution and mixing of the urethane composition and additives such as polyol.

When the solvent, the pinol inhibitor, the antioxidant, or the UV stabilizer is added, when the coating liquid composition is coated to form a photochromic lens, the characteristics of the additive to be added depending on the purpose and characteristics of the photochromic lens configured It may be added by adjusting the amount to be added in consideration.

In the method of coating the coating liquid composition prepared by adding as described above to the lens, pre-treatment with corona, plasma, electron beam, acid or base on the surface of the lens, and the composition according to the present invention on the surface of the pre-treated spectacle lens Coating the coating liquid composition, and curing the coated spectacle lens at 85 ° C. or lower for 3 to 4 minutes to form a film, and second coating the cured film with a general hard coating liquid; The surface of the secondary coating lens is first cured at 75 ~ 85 ℃, then cured (cured curing) for 90 to 120 minutes at 120 ℃ consists of a step of forming a film.

First, the surface of a spectacle lens made of polycarbonate or a conventional spectacle lens is pretreated with corona, plasma, electron beam, acid, or base.

This is to enable the coating liquid composition according to the present invention to improve the adhesion to be coated on the surface of the spectacle lens.

After coating the coating liquid composition according to the present invention on the surface of the pre-treated spectacle lens, the primary coated spectacle lens is cured at 85 ° C or less for 3 to 4 minutes to form a film.

The thickness of the film is to be 0.6 ~ 20㎛, which is for the optimal coating in consideration of the concentration of the color change dye.

After the second coating on the cured film with a general hard coating solution, and then cured for 3 to 4 minutes at 75 ~ 85 ℃ or less, Curing curing (moxicity curing) at 120 ℃ for 90 to 120 minutes.

Stickiness remains on the surface of the film formed on the lens surface after the primary coating, there is no stickiness by the secondary coating, it is possible to form a photochromic lens excellent in impact resistance and scratch resistance and adhesion.

At this time, the general hard coating liquid to be coated with a secondary coating is preferable to use abrasion resistance, scratch resistance, the wear resistance of the primary coated film by using a hard coating liquid consisting of a polymer of poly (meth) acrylate or silicone-based material or Epoxyalkoxysilane And it is possible to configure a photochromic spectacle lens excellent in heat resistance and durability by complementing scratch resistance.

Figure 3 schematically shows the coating sequence of the lens coated in the above manner, by reducing the conventional lens coating layer consisting of four layers to two layers, the technical problem and the production is simple to improve the productivity of the lens product By changing the binder, it is possible to provide a coating liquid composition that can be applied to lenses having various refractive indices, to improve the efficiency of discoloration effect of the coating, and to improve the adhesion of the coating liquid to lenses that are difficult to attach, such as polycarbonate.

Hereinafter, the coating liquid composition and the coating method according to the present invention will be described in detail with reference to Examples.

Example.

Urethane compositions (polyurethane compositions), polyols, epoxy compositions, polyvinyl butyral resins (PVB), photochromic dyes, catalysts and other additives such as polyisocyanate terminated polyurethane prepolymers; The coating liquid composition was prepared by mixing, but the composition was prepared by variously adding the amount and type of additives to be added.

After the above-mentioned coating liquid composition was pretreated by using plasma on the surface of a general spectacle lens, the spectacle lens obtained by first coating the respective coating liquid composition was cured at 85 ° C. or less for 4 minutes to form a film.

After the primary coating, the cured film was first cured at 75 ° C. on the surface of the lens second-coated with a general hard coating solution, and then cured at 120 ° C. for 90 minutes to form a film. The composition was coated on the spectacle lens.

The adhesion test, scratch resistance, hot water resistance, 5˚ bending test, color change, darkening time, fading time and manufacturing time were tested for each of the spectacle lenses that were cured after the first and second coatings. The results are shown in Example Table 1.

Category Example One 2 3 4 5 Urethane composition

HMDI Isocyanurate Trimer 32.7 39.4 20.3 HMDI Uretidione Dimer 27.7 HMDI Biuret Timer 33.3 Polyol

Polyester polyol 30 35 Polyether polyol 50 Polycapolactone polyol 40 40 catalyst


Tinoctylate 0.1 0.2 0.2 Stannous octoate 0.3 DBTDC 0.2 DABCO 0.2 PVB

BL-1 2.5 2.5 BM-2 2.5 BM-5 2.5 2.5 Epoxy composition Diglycidylether of Bisphenol-A 2.5 2.5 solvent

MethylEthyl Ketone 15 5 Toluene 15 20 30 20 22 MCS 2.5 2.5 Anti-phenol

BYK-306 0.5 0.2 0.2 0.2 0.2 BYK-308 0.2 0.2 0.2 0.2 RAD-2200N 0.1 0.1 Antioxidant
Irgafox 1010 0.01 0.01 Songnox 3114 0.02 0.02 0.02 UV stabilizer
Tinuvin-144 0.1 Tinuvin-328 0.1 Photochromic dye






Volcanic gray 0.04 0.04 Midnight gray 0.014 0.014 0.014 Solar yellow 0.002 0.002 0.002 Rush yellow 0.03 0.03 0.03 Corn yellow 0.01 0.01 Ruby 0.005 0.005 Oxford blue Graphite 0.01 0.01 0.01 Lens property after coating


Adhesion test 5 times / 5 times 5 times / 5 times 5 times / 5 times 5 times / 5 times 5 times / 5 times Scratch resistance 6H 6H 7H 6H 7H Hot water resistance Good Good Good Good Good 5˚ bending test Good Good Good Good Good


Color change ○ ○ ○ ○ ○ Darkening time 20 seconds 30 seconds 36 seconds 38 seconds 28 seconds Fading time 3 minutes 3 minutes 7 minutes 13 minutes 6 minutes Manufacture time 5:11 5:34 5:53 5:57 5:41

Among the anti-phenols, BYK is the BYK series of ARTANA, antioxidants and UV stabilizers are from CIBA Specialty Chemical, and photochromic dyes are from JAMES ROBINSON, UK.

As a result of performing the adhesion test on the properties of the lens after the coating, excellent results were obtained in each item. Through this, the coating liquid composition according to the present invention was coated on the spectacle lens, and thus it was found to have an excellent adhesive force. .

The present invention is not limited only to the above-described embodiments, and those skilled in the art can variously modify, change, and substitute the present invention without departing from the spirit and scope of the present invention.

Claims (3)

In the coating liquid for coating for adhesion and color change of the photochromic lens,
A hard coating solution composition for a photochromic lens comprising a urethane composition of a polyisocyanate terminated polyurethane prepolymer, a polyol, an epoxy composition, a polyvinyl butyral resin, a photochromic dye, a catalyst, and other additives.
According to claim 1, Polyurethane isocyanate 20-40% by weight urethane composition of the polyurethane prepolymer, polyol 20-60% by weight, epoxy composition 2-8% by weight, polyvinyl butyral resin 1-5% by weight, light Hard coating liquid composition of a photochromic lens, characterized in that consisting of 0.04 to 0.08% by weight of the color change dye, 0.1 to 0.5% by weight of the catalyst and 0.1 to 35% by weight of other additives.
Primary coating the hard coating solution of the photochromic lens of claim 1 on the surface of the lens;
Curing the lens coated with the coating solution at 85 ° C. or lower for 3 to 4 minutes to form a film;
Second coating the cured film with a general hard coating solution;
Forming a film by first curing the surface of the secondary coated lens at 75 to 85 ° C. for 3 to 4 minutes, and curing at 120 ° C. for 90 to 120 minutes;
Hard coating solution coating method of a photochromic lens, characterized in that consisting of.

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