KR100855216B1 - A reactive naphthopyran compound, a photocromic polymethacrylic polymer coating composition containing the naphthopyran compound, a photocromic polymethacrylic polymer grafted with the naphthopyran, and a photochromic optical article comprising the same - Google Patents

Abstract

The present invention relates to a reactive naphthopyran compound, a photochromic polyacrylic coating liquid composition comprising the same, a photochromic polyacryl, and a photochromic optical article including the same, and more particularly, to the following Chemical Formula 1 or It relates to a reactive naphthopyran compound represented by 2, a photochromic polyacrylic coating liquid composition comprising the same, a photochromic polyacryl grafted with a reactive naphthopyran, and a photochromic optical article comprising the same.

Since the photochromic polyacrylic coating liquid composition of the present invention includes a naphthopyran compound which can be grafted directly to polyacrylic molecules, phase separation does not occur even in the coating liquid, and the photochromic coating film prepared therefrom may be used. There is no blooming phenomenon due to, there is an advantage that the photochromic properties can be maintained for a long time.

[Formula 1] [Formula 2]

In Chemical Formulas 1 and 2, X ¹ to X ⁴ Has the same structure as in the detailed description of the invention.

Responsive, Photochromic, Naphthopyran, Polyacrylic, Graft, Coating Film

Description

Reactive naphthopyran compound, photochromic polyacrylic coating liquid composition comprising the same, photochromic polyacrylic and photochromic optical product comprising the same NAPHTHOPYRAN COMPOUND, A PHOTOCROMIC POLY (METH) ACRYLIC POLYMER GRAFTED WITH THE NAPHTHOPYRAN, AND A PHOTOCHROMIC OPTICAL ARTICLE COMPRISING THE SAME}

[Industrial use]

The present invention relates to a reactive naphthopyran compound, a photochromic polyacrylic coating liquid composition comprising the same, a photochromic polyacrylic and a photochromic optical product comprising the same, and more particularly, a phase separation phenomenon does not occur in the coating liquid. , Reactive naphthopyran compound which does not have a blooming phenomenon over time when manufactured with a coating film, a photochromic polyacrylic coating liquid composition comprising the same, a photochromic polyacryl and a photochromic optical product comprising the same It is about.

 [Private Technology]

Eyewear products such as sunglasses, fashion lenses, over-the-counter and prescription lenses, sports masks, face shields and goggles require transparent plastics that can provide good image quality while reducing incident light to the eye.

In response to this need, considerable attention has been paid to photochromic plastic products used for optical applications. In particular, ophthalmic photochromic plastic lenses have been of interest because of the weight advantages they offer over glass lenses.

Photochromism refers to a phenomenon in which the spectral characteristics of a molecule or crystal are reversibly changed by light or light of a specific wavelength, and thus a color change occurs visually. In general, photochromic materials exhibit a color change (coloring) when exposed to ultraviolet light, and return to their original color or colorless state when the ultraviolet light is blocked.

Eye products where photochromic material (s) are applied to or incorporated into the product exhibit this reversible color change and consequently a reversible light transfer change.

The literature describes that such mechanisms govern the reversible color change, ie the change in the absorption spectrum in the electromagnetic spectrum of visible light (400-700 nm), which is characteristic of different types of organic photochromic compounds. It is.

See, eg, John C. Crano, "Chromogenic Materials (Photochromic)", Kirk-Othmer Encyclopedia of Chemical Technology, 4th edition, 1993, pp. 321-332 describe mechanisms that govern the reversible color change of organic photochromic compounds (eg, indolino spiropyran and indolino spiroxazine) include an electron cyclic mechanism. That is, when exposed to activating ultraviolet light, these organic photochromic compounds are transformed from colorless ring-opening form to colored ring-opening form.

In contrast, the electron cyclization mechanism that governs the reversible color change of photochromic fulgide compounds is believed to involve a transformation from colorless ring-opening forms to colored ring closure forms.

U.S. Pat.Nos. 5,130,353 and 5,185,390 produced photochromic plastic articles by incorporating photochromic materials into plastic substrates by surface absorption techniques. For example, one or more photochromic dyes / compounds may first be applied to the surface of a plastic article as neat photochromic dyes / compounds or in dissolved form in a polymer or other organic solvent carrier, and then the coated surface is heated to By diffusing the photochromic dye / compound (s) into the subsurface area of the lens (commonly referred to as "absorption"), the photochromic dye is incorporated into the subsurface area of a plastic product such as a lens.

U. S. Patent No. 6,187, 444 describes forming an organic photochromic coating on the surface of these plastic substrates in order to enable the use of thermoset polymers, thermoplastic polycarbonates and highly crosslinked optical polymer materials as plastic substrates in photochromic products. Suggested.

The polymer forming the photochromic coating layer as described above changes color or cracks as time passes, and degradation (degradation) occurs that loses its original properties little by little by heat or light. To avoid this problem, most polymer products essentially contain one or more additives of antioxidants, UV blockers, and radical inhibitors.

The additive has the advantage of increasing the life of the photochromic layer by preventing the decomposition of the polymer, but may deteriorate the coating properties when used excessively, a blooming (blooming) phenomenon that the photochromic dye leaks after a long time appears.

Recently, a method of using naphthopyran compounds in photochromic layers has been proposed. However, naphthopy itself does not have reactive functional groups that can be combined with the polyacrylic polymer, and simply exists in a mixed state in the coating film, so phase separation may occur over time, and blooming may still occur. There is a problem.

The present invention is to solve the problems of the prior art as described above, it is an object of the present invention to provide a reactive naphthopyran compound that can be grafted directly to a polyacryl polymer.

Another object of the present invention is to provide a photochromic polyacrylic coating liquid composition comprising the reactive naphthopyran compound.

Still another object of the present invention is to provide a photochromic polyacryl grafted with the reactive naphthopyran compound.

Still another object of the present invention is to provide a photochromic optical product including a coating film prepared from the photochromic polyacrylic coating liquid composition.

The present invention to achieve the above object,

It provides a reactive naphthopyran compound represented by the formula (1) or formula (2):

In Chemical Formulas 1 and 2,

X ¹ to X ⁴ are each independently hydrogen, a hydroxy group, an alkyl group having 1 to 5 carbon atoms; An alkoxy group having 1 to 5 carbon atoms, a hydroxy alkyl group having 1 to 5 carbon atoms, an alkylamine group, a halogen group and a -LP group,

At least one of X ¹ to X ⁴ is a -LP group,

The L is a linker connecting the naphthopyran core and the P, -OOC-, -OOC-R ^1- , -OOC-R ¹ -COO-, -R ² -OOC-R ¹ -COO-, and -OOC-NH-R ³ -NH-COO-, wherein R ¹ And R ² are each independently a branched or straight chain alkyl group having 1 to 20 carbon atoms, and R ³ is a branched or straight chain alkyl group having 1 to 20 carbon atoms and an aromatic group having 6 to 40 carbon atoms,

P is an acrylate or methacrylate group containing a vinyl group, preferably P is represented by the following formula (3):

In Formula 3, R ⁴ is hydrogen or a methyl group, R ⁵ is a branched or straight chain alkyl group having 1 to 5 carbon atoms, a is 0 or 1.

Moreover, this invention is bisphenol-A di (meth) acrylate; Polyethylene glycol di (meth) acrylates; A reactive naphthopyran compound represented by Formula 1 or Formula 2; And it provides a photochromic polyacrylic coating liquid composition comprising an ultraviolet initiator or a thermal initiator.

The present invention also provides a photochromic polyacryl grafted with the reactive naphthopyran compound.

In addition, the present invention provides a photochromic optical article comprising a coating film of 5 to 40 ㎛ thickness prepared from the photochromic polyacrylic coating liquid composition.

In the present invention, the 'di (meth) acrylate' means a diacrylate or dimethacrylate.

Hereinafter, the present invention will be described in more detail.

The naphthopyran compound is represented by the following Chemical Formula a, and is known as a photochromic dye that changes color depending on light irradiation.

 [Formula a]

The naphthopyran compound may be present in a mixed state with a polyacrylic resin precursor or a polyacrylic resin even when mixed with a bisphenol A di (meth) acrylate and a polyethylene glycol di (meth) acrylate in a monomer state to form a coating film. However, it is not possible to form a direct bond with the polyacrylic resin.

However, the 'reactive naphthopyran compound' according to the present invention may be grafted directly to the polyacrylic resin because it contains at least one (meth) acryl group, which is a reactive functional group to be grafted to the polyacrylic resin.

The reactive naphthopyran compound of the present invention is represented by the general formula (1) or (2), and preferred examples thereof include a compound represented by the following general formula (4) or (5).

On the other hand, the present invention is a photochromic polyacrylic coating liquid composition bisphenol A-based di (meth) acrylate; Polyethylene glycol di (meth) acrylates; A reactive naphthopyran compound represented by Formula 1 or Formula 2; And ultraviolet initiators or thermal initiators.

Generally, polyacrylic resins are prepared by polymerization of bisphenol A-based di (meth) acrylate and polyethylene glycol-based di (meth) acrylate, and the reactive naphthopyran compound of the present invention is graft-bonded to the polyacrylic resin. It plays a role in imparting photochromic properties.

In the present invention, the bisphenol A-based di (meth) acrylate is generally used in the manufacture of a polyacrylic resin, so its kind is not particularly limited, but bisphenol A-based ethylene oxide dimethacrylate, bisphenol A At least one selected from the group consisting of a propylene oxide dimethacrylate, a bisphenol A ethylene oxide diacrylate, and a bisphenol A propylene oxide diacrylate is preferable.

In addition, the polyethylene glycol-based di (meth) acrylate may also be used in the production of a general polyacrylic resin can be used, but the type thereof is not particularly limited, triethylene glycol di (meth) acrylate, PEG 600 di (meth) It is preferable that at least 1 sort (s) is chosen from the group which consists of a) acrylate, PEG 400 di (meth) acrylate, and PEG 200 di (meth) acrylate.

In this case, the polyethylene glycol di (meth) acrylate is preferably contained in 25 to 150 parts by weight based on 100 parts by weight of the bisphenol A-based di (meth) acrylate. That is, it is preferable to include at least 25 parts by weight in consideration of flexibility, and preferably at most 150 parts by weight in consideration of the structural properties of the coating layer.

As the reactive naphthopyran compound, a compound represented by Chemical Formula 1 or 2 may be selected and used, and the content may be included in an amount of 1 to 20 parts by weight based on 100 parts by weight of the bisphenol A-based di (meth) acrylate. It is preferable. That is, it is preferable to include at least 1 part by weight in order to exhibit the minimum photochromic properties, and to include at least 20 parts by weight in order to prevent excessive discoloration and to secure the mechanical properties of the coating layer. .

The initiator may be added to those commonly used in the production of polyacrylic resins. In this case, the initiator may be used by selecting an ultraviolet (UV) initiator or a thermal initiator according to the curing method of the coating film, the content is 0.1 to 100 parts by weight of the bisphenol A-based di (meth) acrylate in consideration of the reaction efficiency It is preferably included in 10 parts by weight.

In addition, the coating liquid composition of the present invention may further include an organic solvent, if necessary. The organic solvent is not particularly limited because it may be selected and used within the usual range, but is not particularly limited, benzene, toluene, methyl ethyl ketone, acetone, ethanol, methanol, propanol, isopropanol, tetrahydrofuran, dioxane, ethyl acetate, ethylene One or more selected from the group consisting of glycol, xylene, cyclohexane, and N-methyl pyrrolidinone may be used, and the content thereof is in consideration of the reaction efficiency and the thickness of the coating film. It is preferably included in 10 to 70 parts by weight based on 100 parts by weight of the rate.

On the other hand, the photochromic polyacrylamide of the present invention polymerized from the coating solution composition is characterized in that the reactive naphthopyran compound is graft bonded.

In order for the photochromic polyacryl to exhibit excellent photochromic properties, the reactive naphthopyran compound is 0.1 to the total moles of bisphenol A-based di (meth) acrylate and polyethylene glycol-based di (meth) acrylate. It is preferable to be grafted at a ratio of more than% by weight, and in order to ensure excessive discoloration and mechanical properties of the coating layer, it is preferable to be grafted at a ratio of 1.0% by weight or less. However, the content is just described a preferred example, the scope of the present invention is not limited thereto, and the content of the naphthopyran compound can be arbitrarily adjusted according to the degree of the desired color.

On the other hand, the present invention provides a photochromic optical product comprising a coating film prepared from the photochromic polyacrylic coating liquid composition.

The coating liquid composition is coated by coating on one or both surfaces of the optical substrate and the optical substrate using conventional wet coating methods such as spray coating, spin coating, dip coating, and doctor blading coating, and coating the coating film by ultraviolet or thermal curing. Can be formed.

At this time, the coating film is preferably formed to have a certain degree of transparency in order to be applied to the optical product, it is more preferably manufactured in the form of a photochromic polyacrylic coating film having a thickness of 5 to 40 ㎛.

In addition, the coating and curing process of the polyacrylic coating film is not significantly different from the curing process of the conventional polyacrylic coating film, and since the optimum conditions can be determined within a conventional range, the present invention is not particularly limited. However, in order to obtain more excellent coating film properties, the coated coating liquid may be dried at 60 to 90 ° C. to form a film, and may be prepared by performing a photochromic coating film through UV irradiation and curing.

Industrial products to which such coatings can be applied include those in which photochromic materials are typically used, such as optical lenses, flat lenses, face shields, goggles, camera lenses, windows, automotive transparents, inks, decorations, It can be used for films, sheets, coatings, paints and protective documents (such as passports, driver's licenses and check marks on bank notes).

Hereinafter, preferred embodiments of the present invention are described. However, the following examples are only preferred embodiments of the present invention, and the present invention is not limited to the following examples.

[Response type Naphthopyran  Preparation of Compound

Example  One

According to Scheme 1 below, a reactive naphthopyran compound represented by Chemical Formula 4 was prepared.

Scheme 1

(Preparation of Compound of Formula 7)

10.0 g (62.0 mmol) of 2,7-dihroxynaphthalene represented by Chemical Formula 6, pyridinium-p-toulenesulfonate 0.65 g (2.6 mmol), and A solution of 11.0 g (104 mmol) of trimethyl orthoformate dissolved in 30 mL of ethylene chloride; and 1,1-diphenyl-2-propyn-1-ol (1,1-diphenyl -2-propyn-1-ol) 6.0 g (29.0 mmol) dissolved in 20 mL of ethylene chloride (ethylene chloride) was mixed to prepare a reaction mixture.

After the reaction mixture was reacted at reflux for 2 hours while boiling, the reaction mixture was cooled to room temperature (about 25 ° C.), and the solvent was evaporated in vacuo. The organic layer obtained from this was dried over anhydrous sodium sulfate and condensed under reduced pressure.

The reaction product obtained in the above process was passed through a silica gel chromatography ( n- hexane: ethyl acetate = 1: 2 volume ratio) apparatus to obtain a purple solid represented by Chemical Formula 7 in Scheme 1 (4.0 g, yield 40%). ; ¹ H NMR (500 MHz, CDCl ₃ ): δ = 6.24 (d, 1H), 6.92 (d, 1H), 7.07.17 (d, 1H), 7.26 (m, 2H), 7.27 (s, 1H), 7.33 (m, 4 H), 7.49 (d, 4 H), 7.6 (q, 2 H).

(Preparation of Compound of Formula 8)

900 mg (2.57 mmol) of the compound of Formula 7 and 32 g (0.26 mmol) of dimethylaminopyridine (DMAP) were dissolved in 10 mL of dichloromethane (CH ₂ Cl ₂ ), followed by glutaric anhydride. 290 mg (2.57 mmol) was added. The reaction mixture was then reacted at reflux for 4 hours with boiling. The organic layer obtained from this was dried over anhydrous sodium sulfate and condensed under reduced pressure.

The reaction product obtained in the above process was passed through a silica gel chromatography ( n- hexane: ethyl acetate = 1: 1 volume ratio) apparatus to obtain a compound represented by Chemical Formula 8 in Scheme 1 (620 mg, yield 52%); ¹ H NMR (500 MHz, CDCl ₃ ): δ = 2.11 (q, 2H), 2.55 (t, 2H), 2.71 (t, 2H), 6.25 (d, 1H), 7.03 (dd, 1H), 7.18 ( t, 2H), 7.24 (m, 2H), 7.29 (m, 4H), 7.45 (m, 4H), 7.63 (m, 2H), 7.71 (d, 1H).

(Preparation of Compound of Formula 4)

Compound 310 mg (0.67 mmol) of Formula 8, N - (3- dimethylaminopropyl) - N '- ethylcarbodiimide 288 mg (1.01 mmol) and DMAP 9 mg (0.07 mmol) in dichloromethane (CH ₂ Cl ₂ ) After dissolving in 10 mL, 0.14 mL (1.01 mmol) of hydroxypropyl methacrylate was added. The reaction mixture was then reacted at reflux for 4 hours with boiling. The organic layer obtained from this was dried over anhydrous sodium sulfate and condensed under reduced pressure.

The reaction product obtained in the above process was passed through a silica gel chromatography ( n- hexane: ethyl acetate = 1: 1 volume ratio) apparatus to obtain a compound represented by Chemical Formula 4 in Scheme 1 (201 mg, yield 52%); ¹ H NMR (500 MHz, CDCl ₃ ): δ = 1.30 (dd, 3H), 1.95 (m, 2H), 2.09 (m, 2H), 2.50 (m, 2H), 2.69 (m, 2H), 5.56 ( d, 1H), 5.61 (m, 2H), 6.11 (d, 1H), 6.12 (m, 2H), 6.26 (dd, 1H), 7.04 (d, 1H), 7.18 (m, 4H), 7.26 (m , 4H), 7.46 (m, 4H), 7.63 (m, 2H), 7.71 (d, 1H).

Example  2

According to Scheme 2 below, a reactive naphthopyran compound represented by Chemical Formula 5 was prepared.

Scheme 2

(Compound Preparation of Formula 10)

3.0 g (5.9 mmol) of the compound represented by Chemical Formula 9 of Formula 2 and 0.9 g (11.8 mmol) of glutaric anhydride were dissolved in 100 mL of dichloromethane (CH ₂ Cl ₂ ) to prepare a reaction mixture. After the preparation, the reaction mixture was reacted under reflux with boiling for 8 hours in the presence of dimethylaminopyridine (DMAP) corresponding to about 1% by weight of the catalyst.

After the reaction, the reaction mixture was cooled to room temperature (about 25 ° C.) and washed with brine (100 mL × 3). The organic layer obtained from this was dried over anhydrous MgSO ₄ , filtered, and the solvent was evaporated in vacuo.

The reaction product remaining in the above process was passed through a silica gel chromatography ( n- hexane: ethyl alcohol = 1: 1 volume ratio) apparatus to obtain a dark green solid represented by Chemical Formula 10 (2.1 g, yield 60%); ¹ H NMR (500 MHz, CDCl ₃ ): δ = 1.95 (quintet, 2H), 2.05 (m, 4H), 2.40 (q, 4H), 2.90 (s, 6H), 3.41 (m, 4H), 3.75 ( s, 3H), 5.23 (s, 2H), 6.15 (d, 1H), 6.66 (d, 1H), 6.80 (t, 3H), 6.93 (d, 1H), 7.13 (s, 1H), 7.19 (s , 1H), 7.34 (d, 2H), 7.43 (d, 2H), 7.54 (d, 1H).

(Compound Preparation of Formula 5)

The 416 mg (0.67 mmol) compound of Formula 10, N - (3- dimethylaminopropyl) - N '- ethylcarbodiimide 288 mg (1.01 mmol) and DMAP 9.0 mg (0.07 mmol) in dichloromethane (CH ₂ Cl ₂ ) After dissolving in 10 mL, 0.14 mL (1.01 mmol) of hydroxypropyl methacrylate was added. The reaction mixture was then reacted by refluxing for 4 hours with boiling.

The organic layer obtained therefrom was dried over anhydrous sodium sulfate, and condensed under reduced pressure to obtain a compound represented by Chemical Formula 5.

[Response type Polyacrylic Of coating film  Produce]

UV curable

Production Example  One

38 g of a UV curable coating solution (manufactured by LG Chemical, AU21PC: a reactive polyacrylic coating solution containing a diacrylate mixture, vinyl, and polyacryl) was added thereto, and 0.76 g of a reactive naphthopyran compound represented by Chemical Formula 4 was added thereto. After injection, 0.38 g of Irgacure 184 and Irgacure 819, which are photo initiators, were added as initiators, respectively, and stirred for 1 hour at room temperature to prepare a coating composition.

The coating composition was roll-coated with meyer bar # 30 on the surface of the polycarbonate film (0.8 mm thick I-component), followed by preliminary drying in an oven at 80 ° C. for 5 minutes to volatilize the solvent. Subsequently, the obtained film was irradiated with 2,000 mJ / cm 2 by an ultraviolet curing machine to prepare a coating film.

Production Example  2

A photochromic polyacrylic coating was prepared in the same manner as in Preparation Example 1, except that 0.76 g of a reactive naphthopyran compound of Formula 5 was used.

Comparative example  One

A photochromic polyacrylic coating film was prepared in the same manner as in Preparation Example 1, except that 0.76 g of a general naphthopyran compound represented by Chemical Formula a was used.

[Formula a]

(Ii) thermosetting

Production Example  3

A coating composition was prepared in the same manner as in Preparation Example 1, except that 0.04 g of V-65 (2,2'-Azobis (2,4-dimethyl valeronitrile)) manufactured by Wako, which is a thermal initiator, was used as an initiator.

The prepared composition was roll coated with meyer bar # 30 on the surface of a polycarbonate film (0.8 mm thick I-component), and dried and cured in an oven at 75 ° C. for 120 minutes to prepare a coating film.

Production Example  4

A photochromic polyacrylic coating film was prepared in the same manner as in Preparation Example 3, except that 0.76 g of a reactive naphthopyran compound of Formula 5 was used.

Comparative example  2

A photochromic polyacrylic coating film was prepared in the same manner as in Preparation Example 3, except that 0.76 g of the general naphthopyran compound represented by Chemical Formula (a) was used.

[ Photochromic Polyacrylic Of coating film  Property measurement]

In order to determine the physical properties of the photochromic polyacrylic coating film prepared according to Preparation Examples 1 to 4, and Comparative Examples 1 and 2, the following experiment was performed, and the results are shown in Table 1 below.

(1) optical density (OD)

The cured coating film was irradiated with ultraviolet rays (1.35 mW / cm ² ) having a wavelength of 365 nm for 5 minutes, and then immediately measured by using a UV-Vis detector to measure output light in decolorized and colored states, respectively. At this time, ΔOD was calculated according to the following formula (1).

[Calculation 1]

(2) Desorption speed  ( t _{One /2} )

The transmittance at the λ _max wavelength of the sample exposed to ultraviolet light under the same conditions as the optical density (OD) measurement was measured by the time taken to recover to half of the complete decolorization state after the light source was removed.

(3) weather resistance ( T _{One /2} )

Each sample was irradiated for 8 hours at a wavelength of 340 nm, a light quantity of 0.77 W / m ² , and 60 ° C. using a UVA fluorescent lamp in ATLAS UV 2000, an accelerated weathering tester, and condensation was performed at 50 ° C. for 4 hours. After repeating the process (ASTM G 154-99), the optical density was measured and measured by the time taken for the absorption intensity at the initial λ _max wavelength to decrease by half.

(4) membrane strength

The film strength of the UV cured photochromic layer was measured using the Fischer microhardness measuring method.

(5) film thickness

The film thickness was measured by observing the cross section using a micrometer.

division Preparation Example 1 Preparation Example 2 Preparation Example 3 Preparation Example 4 Comparative Example 1 Comparative Example 2 ΔOD _max 0.35 0.45 0.45 0.72 0.30 0.42 λ _{max (nm)} 431 490 430 490 425 432 t _1/2 (sec) 85 345 35 285 28 15 T _1/2 (hr) 100 75 180 120 85 95 Fisher Microhardness (N / mm ² )  167  165  154  153  150  135 Film thickness (㎛) 20 20 18 18 18 17

As shown in Table 1, the polyacrylic coating film grafted with the reactive naphthopyran compound according to the present invention can be seen that the optical density is high, the discoloration time is short, the discoloration is excellent, and the durability is excellent.

Since the photochromic polyacrylic coating liquid composition of the present invention includes a reactive naphthopyran compound which can be grafted directly to polyacryl molecules, phase separation does not occur even in the coating liquid, and the photochromic coating film prepared therefrom is There is no blooming phenomenon with elapsed, and there is an advantage that the photochromic property can be maintained for a long time.

Claims (9)

Reaction type naphthopyran compound represented by the following general formula (1) or (2): [Formula 1] [Formula 2]

In Chemical Formulas 1 and 2, X ¹ to X ⁴ are each independently hydrogen, a hydroxy group, an alkyl group having 1 to 5 carbon atoms; An alkoxy group having 1 to 5 carbon atoms, a hydroxy alkyl group having 1 to 5 carbon atoms, an alkylamine group, a halogen group and a -LP group, At least one of X ¹ to X ⁴ is a -LP group, The L is a linker connecting the naphthopyran core and the P, -OOC-, -OOC-R ^1- , -OOC-R ¹ -COO-, -R ² -OOC-R ¹ -COO-, and -OOC-NH-R ³ -NH-COO-, wherein R ¹ And R ² are each independently a branched or straight chain alkyl group having 1 to 20 carbon atoms, and R ³ is a branched or straight chain alkyl group having 1 to 20 carbon atoms, or an aromatic group having 6 to 40 carbon atoms, P is an acrylate or methacrylate group containing a vinyl group. Bisphenol A type di (meth) acrylate; Polyethylene glycol di (meth) acrylates; Reaction type naphthopyran compound represented by Formula 1 or Formula 2 of claim 1; And Ultraviolet initiator or heat initiator for polymerization reaction of the said bisphenol-A di (meth) acrylate and polyethyleneglycol di (meth) acrylate Photochromic polyacrylic coating liquid composition comprising a. The method of claim 2, To 100 parts by weight of the bisphenol A-based di (meth) acrylate, 25 to 150 parts by weight of the polyethylene glycol di (meth) acrylate; 1 to 20 parts by weight of the reactive naphthopyran compound; And 0.1 to 10 parts by weight of the initiator Photochromic polyacrylic coating liquid composition comprising a. The method of claim 2, The bisphenol A-based di (meth) acrylate is bisphenol A-based ethylene oxide dimethacrylate, bisphenol A-based propylene oxide dimethacrylate, bisphenol A-based ethylene oxide diacrylate, and bisphenol A-based propylene oxide diacrylate Photochromic polyacrylic coating liquid composition which is selected from the group consisting of one or more. The method of claim 2, The polyethylene glycol di (meth) acrylate is composed of triethylene glycol di (meth) acrylate, PEG 600 di (meth) acrylate, PEG 400 di (meth) acrylate, and PEG 200 di (meth) acrylate. Photochromic polyacrylic coating liquid composition which is selected from one or more of the group. The method of claim 2, The reactive naphthopyran compound is a photochromic polyacrylic coating liquid composition selected from the group consisting of compounds represented by the following formula (4) and (5). [Formula 4]

[Formula 5]

Photochromic polyacryl grafted with the reactive naphthopyran compound represented by Formula 1 or Formula 2. The method of claim 7, wherein The polyacryl is grafted at a ratio of 0.1 to 1.0 mol% based on the total number of moles of the bisphenol A di (meth) acrylate and polyethylene glycol di (meth) acrylate. Photochromic polyacrylic. A photochromic polyacrylic coating film prepared from the photochromic polyacrylic coating liquid composition according to any one of claims 2 to 6 and having a thickness of 5 to 40 µm. Photochromic optics comprising a.