JP2008214397A - Coating composition and plastic lens using the same - Google Patents

Abstract

To provide a coating composition capable of forming a hard coat film having sufficient adhesion to a high refractive index plastic lens substrate.
SOLUTION: (A) Titanium oxide-containing composite oxide fine particles, and (B) the following general formula: R ¹ _a R ² _b Si (OR ³ ) _{4- (a + b)} (1) (in formula (1), R ¹ represents an organic group having a functional group or an organic group having 4 to 14 carbon atoms having an unsaturated double bond, R ² represents a hydrocarbon group or halogenated hydrocarbon group having 1 to 6 carbon atoms, R ³ represents an alkyl group having 1 to 4 carbon atoms, an alkoxyalkyl group, or an acyl group, a and b each represents 0 or 1, and a + b represents 1 or 2.) A coating composition comprising: a hydrolyzate; (C) iron (III) ethylenediaminetetraacetate; and (D) an acetylacetonate metal complex compound.
[Selection figure] None

Description

  The present invention relates to a coating composition and a plastic lens using the same.

  Plastic lenses are widely used for eyeglasses because they have higher moldability, processability, and safety than glass lenses. However, in plastic lenses, the weakness (scratch resistance) against scratches due to insufficient hardness of the plastic itself becomes a problem, and as a plastic lens, there are widely used those in which a hard coat film is formed on the surface of a plastic lens substrate. It is used.

  In addition, the coating composition for forming such a hard coat film has conventionally been composed mainly of silicon oxide fine particles. However, as the refractive index of plastic lenses increases, interference fringes are formed on the hard coat film. There was a problem that I could see and look bad. Therefore, instead of silicon oxide fine particles, a coating composition mainly composed of composite oxide fine particles made of a metal oxide having a high refractive index such as titanium oxide, tin oxide, tungsten oxide, and zirconium oxide has been proposed. Yes.

  Furthermore, as a coating composition for a plastic lens having a high refractive index, for example, JP-A-07-168002 (Patent Document 1) discloses fine particles of a composite oxide of titanium oxide and zirconium oxide, and an organosilicon compound or A coating composition containing the hydrolyzate is disclosed, and in the specification a coating composition further containing a metal complex compound is described. Japanese Patent Laying-Open No. 2006-89749 (Patent Document 2) discloses a coating composition containing an acetylacetonate metal complex compound.

However, in the hard coat film obtained by using the coating composition as described in the above-mentioned patent document etc., the problems of scratch resistance and interference fringes are solved, but the plastic lens substrate having a high refractive index and It is not always satisfactory in terms of adhesion to the hard coat film, and there is a problem that the adhesion of the hard coat film is remarkably lowered (inferior in weather resistance) particularly when exposed to sunlight or the like. .
Japanese Patent Laid-Open No. 07-168002 JP 2006-89749 A

  The present invention has been made in view of the above-mentioned problems of the prior art, has sufficient scratch resistance, and is excellent in weather resistance, for example, even when exposed to sunlight for a long period of time. It is an object of the present invention to provide a coating composition capable of forming a hard coat film having sufficient adhesion to a plastic lens substrate, and a plastic lens using the same.

  As a result of intensive studies to achieve the above object, the inventors of the present invention contain titanium oxide-containing composite oxide fine particles and an organosilicon compound as main components, and include ethylenediaminetetraacetic acid iron (III) and a specific acetylacetonate. According to the coating composition further containing a metal complex compound, it has sufficient scratch resistance and excellent weather resistance, for example, even when exposed to sunlight for a long period of time, a high refractive index plastic lens substrate. The present inventors have found that a hard coat film having sufficient adhesiveness can be formed and completed the present invention.

That is, the coating composition of the present invention comprises (A) titanium oxide-containing composite oxide fine particles,
(B) The following general formula:
R ¹ _a R ² _b Si (OR ³ ) _{4- (a + b)} (1)
(In formula (1), R ¹ represents an organic group having a functional group or an organic group having 4 to 14 carbon atoms having an unsaturated double bond, and R ² represents a hydrocarbon group having 1 to 6 carbon atoms or a halogenated group. A hydrocarbon group, R ³ represents an alkyl group having 1 to 4 carbon atoms, an alkoxyalkyl group or an acyl group, a and b each represent 0 or 1, and a + b represents 1 or 2.
An organosilicon compound represented by the formula:
(C) ethylenediaminetetraacetic acid iron (III);
(D) An acetylacetonate metal whose central metal is at least one metal selected from the group consisting of lithium, copper, zinc, cobalt, nickel, manganese, chromium, zirconium, magnesium, iron, calcium, bismuth, and aluminum A complex compound;
It is characterized by containing.

  Moreover, in the coating composition of this invention, it is preferable to further contain (E) ethylenediaminetetraacetic acid aluminum.

  Furthermore, in the coating composition of this invention, content of the said (C) ethylenediaminetetraacetic acid iron (III) is 0.5-10 with respect to 100 mass parts of said (B) organosilicon compounds or its hydrolyzate. It is preferable that it is the quantity used as the range of a mass part.

  Moreover, in the coating composition of this invention, content of the said (D) acetylacetonate metal complex compound is 0.1-15 mass with respect to 100 mass parts of said (B) organosilicon compound or its hydrolyzate. The amount is preferably in the range of parts.

  Furthermore, in the coating composition of this invention, content of the said (E) ethylenediaminetetraacetate is 0.5-10 mass parts with respect to 100 mass parts of said (B) organosilicon compound or its hydrolyzate. The amount is preferably in the range.

  The plastic lens of the present invention comprises a plastic lens substrate having a refractive index of 1.60 or more, and a hard coat film formed on the surface of the plastic lens substrate and formed from the coating composition. To do.

  According to the present invention, it has sufficient scratch resistance and excellent weather resistance, for example, sufficient adhesion to a high refractive index plastic lens substrate even when exposed to sunlight for a long period of time. It is possible to provide a coating composition capable of forming a hard coat film having the same, and a plastic lens using the same.

  Hereinafter, the present invention will be described in detail with reference to preferred embodiments thereof.

  First, the coating composition of the present invention will be described. That is, the coating composition of the present invention comprises (A) titanium oxide-containing composite oxide fine particles, (B) an organosilicon compound or a hydrolyzate thereof, (C) iron (III) ethylenediaminetetraacetate, and (D ) An acetylacetonate metal complex compound is contained.

  The (A) titanium oxide-containing composite oxide fine particles according to the present invention are composite oxide fine particles containing titanium oxide. Such composite oxide fine particles are used as a sol in which the composite oxide is dispersed in water, methanol, other organic solvents, or the like. Moreover, it is preferable that the particle diameter of such composite oxide fine particles is in the range of 1 to 100 nm. If the particle diameter is less than the lower limit, the stability of the titanium oxide-containing composite oxide sol itself is also deteriorated, and the production of the sol tends to be difficult. On the other hand, if the upper limit is exceeded, the stability of the coating composition is obtained. The transparency and smoothness of the hard coat film tend to decrease.

  Such a complex oxide is a compound of titanium oxide and another metal oxide. Examples of other metal oxides that can be used in combination with titanium oxide are not particularly limited. For example, zirconium oxide, silicon oxide, tin oxide, iron oxide, aluminum oxide, antimony oxide, cerium oxide, and oxidation. Examples thereof include zinc, beryllium oxide, tungsten oxide, tantalum oxide, lanthanum oxide, indium oxide, and niobium oxide. These other metal oxides can be used alone or in combination of two or more. Examples of such a titanium oxide-containing composite oxide include titanium oxide / zirconium oxide composite oxide, titanium oxide / zirconium oxide / silicon dioxide composite oxide, titanium oxide / iron oxide / silicon dioxide composite oxide, and oxidation. Titanium / tin oxide / zirconium oxide / silicon dioxide composite oxide, titanium oxide / silicon dioxide composite oxide, titanium oxide / tin oxide / zirconium oxide composite oxide, titanium oxide / zirconium oxide / silicon dioxide / antimony oxide composite oxide Can be mentioned. Among these, from the viewpoint of scratch resistance and weather resistance of the obtained hard coat film, titanium oxide / tin oxide / zirconium oxide / silicon dioxide composite oxide, titanium oxide / zirconium oxide / silicon dioxide composite oxide, titanium oxide / A tin oxide / zirconium oxide composite oxide and a titanium oxide / zirconium oxide / silicon dioxide / antimony oxide composite oxide are preferred.

  Moreover, the content ratio of titanium oxide in such a titanium oxide-containing composite oxide is not particularly limited, but is preferably in the range of 10 to 95% by mass. If the content ratio of titanium oxide is less than the lower limit, a refractive index sufficient to reduce interference fringes tends not to be obtained. On the other hand, if the content exceeds the upper limit, the hard coat is exposed to sunlight or the like. There is a tendency to cause a problem that the film is easily discolored. In addition, the refractive index of the hard coat film | membrane obtained can also be adjusted by adjusting the content rate of a titanium oxide.

The (B) organosilicon compound according to the present invention has the following general formula:
R ¹ _a R ² _b Si (OR ³ ) _{4- (a + b)} (1)
It is represented by

In the general formula (1), R ¹ represents an organic group having a functional group or an organic group having 4 to 14 carbon atoms having an unsaturated double bond. R ² represents a hydrocarbon group having 1 to 6 carbon atoms or a halogenated hydrocarbon group. R ³ represents an alkyl group having 1 to 4 carbon atoms, an alkoxyalkyl group, or an acyl group. A and b each represent 0 or 1, and a + b represents 1 or 2.

In the general formula (1), R ¹ is preferably an organic group having an epoxy group as a functional group. Thus, the organosilicon compound which has an epoxy group as a functional group is called an epoxy silane. Examples of such organosilicon compounds include γ-glycidoxypropyltrimethoxysilane, γ-glycidoxypropyltriethoxysilane, γ-glycidoxypropyltriacetoxysilane, and γ-glycidoxypropylmethyl. Examples include dimethoxysilane, γ-glycidoxypropylmethyldiethoxysilane, and β- (3,4-epoxycyclohexyl) ethyltriethoxysilane. In addition, among the organosilicon compounds represented by the general formula (1), as the organosilicon compounds other than those in which R ¹ has an epoxy group as a functional group (including those having a = 0), for example, methyltri Methoxysilane, methyltriethoxysilane, vinyltrimethoxysilane, vinyltriethoxysilane, γ-methacryloxypropyltrimethoxysilane, aminomethyltrimethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, phenyl Trialkoxysilane compounds such as trimethoxysilane, phenyltriethoxysilane, γ-chloropropyltrimethoxysilane, γ-mercaptopropyltriethoxysilane, 3,3,3-trifluoropropyltrimethoxysilane; vinyltriacetoxysilane, etc. bird Acyloxysilane compounds; trialkoxyalkoxysilane compounds such as vinyltrimethoxyethoxysilane. These organosilicon compounds can be used individually by 1 type or in combination of 2 or more types.

  The organosilicon compound (B) according to the present invention may be used as it is, but it is used as a hydrolyzate of the organosilicon compound from the viewpoint of increasing the reaction rate of the resulting coating composition and lowering the curing temperature. You can also

  The coating composition of the present invention contains (A) titanium oxide-containing composite oxide fine particles and (B) an organosilicon compound or a hydrolyzate thereof as the main components. As a content ratio of the (A) titanium oxide-containing composite oxide fine particles and the (B) organosilicon compound or a hydrolyzate thereof in the coating composition of the present invention, a mass ratio (the above (A): the above ( In B)), it is preferably in the range of 1: 0.5 to 1:10, more preferably in the range of 1: 0.5 to 1: 3. When the content ratio of the (B) organosilicon compound or its hydrolyzate is less than the lower limit, cracks may occur in the obtained hard coat film, and sufficient adhesion to the lens substrate may be ensured. On the other hand, when the above upper limit is exceeded, it tends to be difficult to sufficiently ensure the refractive index and scratch resistance of the obtained hard coat film. In addition, the refractive index of the hard coat film | membrane obtained can also be adjusted by adjusting these content rates.

  The coating composition of the present invention comprises (C) iron (III) ethylenediaminetetraacetate and (D) in addition to (A) titanium oxide-containing composite oxide fine particles and (B) organosilicon compound or a hydrolyzate thereof. It contains an acetylacetonate metal complex compound. Thus, by using a coating composition containing both (C) iron (III) ethylenediaminetetraacetate and (D) acetylacetonate metal complex compound, it has sufficient scratch resistance and excellent weather resistance. A hard coat film can be formed. Moreover, by adding such (C) ethylenediaminetetraacetic acid iron (III) and (D) acetylacetonate metal complex compounds, (B) the three-dimensional structure forming reaction of the organosilicon compound or the hydrolyzate thereof is carried out. The effect of promoting or the effect of extending the pot life of the resulting coating composition can also be obtained.

  In such (D) acetylacetonate metal complex compound, the central metal is lithium (Li), copper (Cu), zinc (Zn), cobalt (Co), nickel (Ni), manganese (Mn), chromium ( Acetylacetonate metal, which is at least one metal selected from the group consisting of Cr), zirconium (Zr), magnesium (Mg), iron (Fe), calcium (Ca), bismuth (Bi), and aluminum (Al) It is a complex compound. Among these acetylacetonate metal complex compounds, aluminum acetylacetonate and iron (III) acetylacetonate are preferable from the viewpoint of ensuring sufficient scratch resistance and weather resistance. Moreover, these acetylacetonate metal complex compounds can be used individually by 1 type or in combination of 2 or more types.

  Moreover, in the coating composition of this invention, content of the said (C) ethylenediaminetetraacetic acid iron (III) is 0.5-10 with respect to 100 mass parts of said (B) organosilicon compounds or its hydrolyzate. The amount is preferably in the range of parts by mass, and more preferably in the range of 1 to 5 parts by mass. When the content is less than the lower limit, the weather resistance of the resulting hard coat film tends to be insufficient, and when it exceeds the upper limit, the stability of the coating composition (coating liquid) tends to be impaired.

  Furthermore, in the coating composition of this invention, content of the said (D) acetylacetonate metal complex compound is 0.1-15 mass with respect to 100 mass parts of said (B) organosilicon compound or its hydrolyzate. The amount is preferably in the range of parts by weight, and more preferably in the range of 0.5 to 10 parts by weight. If the content is less than the lower limit, the scratch resistance of the resulting hard coat film tends to be insufficient. On the other hand, if the content exceeds the upper limit, cracks may occur in the obtained hard coat film and the lens. There is a tendency that sufficient adhesion to the substrate cannot be ensured.

  Moreover, in the coating composition of this invention, it is preferable to further contain (E) ethylenediaminetetraacetic acid aluminum. By using such (E) ethylenediaminetetraacetic acid aluminum together with the (C) ethylenediaminetetraacetic acid iron (III) and the (D) acetylacetonate metal complex compound, the scratch resistance of the resulting hard coat film is further increased. Can be improved.

  When such (E) ethylenediaminetetraacetic acid aluminum acetate is used, the content thereof is in the range of 0.5 to 10 parts by mass with respect to 100 parts by mass of the (B) organosilicon compound or its hydrolyzate. It is preferable that it is a quantity, and it is more preferable that it is the quantity used as the range of 1-5 mass parts. When the content is less than the lower limit, the effect of improving the scratch resistance of the obtained hard coat film tends to be insufficient, and when the content exceeds the upper limit, the stability of the coating liquid tends to be impaired. When such (E) ethylenediaminetetraacetic acid aluminum is used, the total amount of (E) ethylenediaminetetraacetic acid aluminum content and (C) ethylenediaminetetraacetic acid iron (III) content, (B) It is preferable to set it as the quantity used as 10 mass parts or less with respect to 100 mass parts of organosilicon compounds or its hydrolyzate, and it is more preferable to set it as the quantity used as 5 mass parts or less. When these contents exceed the upper limit, the stability of the coating liquid tends to be impaired.

  Furthermore, the coating composition of the present invention may further contain a solvent as necessary in order to make the coating composition liquid or to lower the viscosity. Examples of such a solvent include water, lower alcohol, acetone, ether, ketone, and ester. Moreover, the coating composition of this invention may contain various additives further as needed. Examples of such additives include pH adjusters, viscosity modifiers, leveling agents, matting agents, dyes, pigments, stabilizers, ultraviolet absorbers, and antioxidants.

  According to the coating composition of the present invention as described above, it has sufficient scratch resistance and is excellent in weather resistance. For example, even when exposed to sunlight for a long period of time, it has a high refractive index plastic lens base. A hard coat film having sufficient adhesion to the material can be formed.

  As a method for forming a hard coat film using the coating composition of the present invention, for example, the coating composition of the present invention is applied to a plastic lens substrate and then thermally cured, whereby the surface of the plastic lens substrate is hardened. A method of forming a coat film can be employed.

  As such an application means, a normal coating method such as brush coating, dipping, roll coating, spray coating, or flow coating can be used. Furthermore, the coating film thickness of the coating composition is preferably such that the thickness of the hard coat film after curing is in the range of 0.5 to 6 μm. Furthermore, the temperature of thermosetting is preferably in the range of 70 to 130 ° C. In addition, after applying the coating composition of the present invention to a mold, the raw material of the plastic lens base material may be cast polymerized to mold the plastic lens base material, or the coating composition of the present invention may be formed into a molded product. After coating, the surface of the coating film that has not been cured may be brought into close contact with the mold, and the coating film may be cured thereon.

  Further, such a plastic lens substrate is not particularly limited to one having a high refractive index. Furthermore, as a raw material of such a plastic lens substrate, for example, polymethyl methacrylate and its copolymer, acrylonitrile-styrene copolymer, polycarbonate, cellulose acetate, polyvinyl chloride, polyethylene terephthalate, epoxy resin, unsaturated polyester Examples include resins, polyurethane resins, and polymers of diethylene glycol bisallyl carbonate (CR-39).

  Next, the plastic lens of the present invention will be described. That is, the plastic lens of the present invention includes a plastic lens substrate having a refractive index of 1.60 or more and a hard coat film formed from the coating composition formed on the surface of the plastic lens substrate. It is a feature.

  Thus, as a raw material of a high refractive index plastic lens base material having a refractive index of 1.60 or more, for example, a thiourethane resin or an episulfide resin can be used. Moreover, as a method of forming a hard coat film using the coating composition, the method as described above can be employed.

  EXAMPLES Hereinafter, although this invention is demonstrated more concretely based on an Example and a comparative example, this invention is not limited to a following example.

(Preparation Example 1)
45 parts by mass of γ-glycidoxypropyltrimethoxysilane was added to the reaction vessel, and 10 parts by mass of 0.1N hydrochloric acid aqueous solution was gradually added dropwise with stirring to obtain an organosilicon compound hydrolyzate.

(Example 1)
With respect to 55 parts by mass of the hydrolyzate of the organosilicon compound obtained in Preparation Example 1, titanium oxide / zirconium oxide / silicon dioxide composite oxide sol (methanol dispersion, manufactured by Catalyst Kasei Kogyo Co., Ltd., solid content: 30 mass) %) 120 parts by mass were added, and then 1 part by mass of ethylenediaminetetraacetate and 0.5 parts by mass of ethylenediaminetetraacetate were dissolved in 25 parts by mass of pure water and added. Thereafter, an aluminum acetylacetonate solution in which 1 part by mass of aluminum acetylacetonate was dissolved in 45 parts by mass of methanol was further added to the reaction vessel, and then 5 parts by mass of tetraethoxysilane and surfactant L-7001 (Toray Dow Corning) (Product made) After adding 0.5 mass part, it stirred and obtained the coating composition.

  Next, a plastic lens substrate having a refractive index of 1.67 (manufactured by Nikon Essilor, product name “Nikonlite 4AS400”) was prepared, and washed and alkali-treated. Then, the coating composition obtained on such a plastic lens substrate is applied by a dip coating method so that the film thickness becomes 2.0 μm, and cured at a temperature of 100 ° C. for 4 hours to obtain a plastic lens with a hard coat. Obtained.

(Example 2)
A coating composition and a hard-coated plastic lens were obtained in the same manner as in Example 1 except that the amount of iron ethylenediaminetetraacetate added was 0.5 parts by mass.

(Example 3)
A coating composition and a hard-coated plastic lens were obtained in the same manner as in Example 1 except that the amount of iron ethylenediaminetetraacetate added was 0.25 parts by mass.

Example 4
Instead of titanium oxide / zirconium oxide / silicon dioxide composite oxide sol (methanol dispersion, manufactured by Catalyst Kasei Kogyo Co., Ltd., solid content: 30% by mass), titanium oxide / iron oxide / silicon dioxide composite oxide sol (methanol) A coating composition and a hard-coated plastic lens were obtained in the same manner as in Example 1 except that the dispersion, produced by Catalyst Chemical Industry Co., Ltd., solid content: 30% by mass) was used.

(Example 5)
In place of 120 parts by mass of titanium oxide / zirconium oxide / silicon dioxide composite oxide sol (methanol dispersion, manufactured by Catalyst Kasei Kogyo Co., Ltd., solid content: 30% by mass), titanium oxide / tin oxide / zirconium oxide / silicon dioxide Example 1 except that 180 parts by mass of a composite oxide sol (methanol dispersion, manufactured by Catalyst Chemical Industry Co., Ltd., solid content: 20% by mass) was used, and the amount of methanol in the aluminum acetylacetonate solution was 5 parts by mass. In the same manner as above, a coating composition and a plastic lens with a hard coat were obtained.

(Example 6)
A coating composition and a hard-coated plastic lens were obtained in the same manner as in Example 1 except that ethylenediaminetetraacetate aluminum was not added.

(Comparative Example 1)
A coating composition and a hard-coated plastic lens were obtained in the same manner as in Example 1 except that no ethylenediaminetetraacetic acid iron was added.

(Comparative Example 2)
A coating composition and a plastic lens with a hard coat were obtained in the same manner as in Example 1 except that no ethylenediaminetetraacetic acid iron was added and the amount of ethylenediaminetetraacetic acid aluminum added was 1.5 parts by mass.

(Comparative Example 3)
A coating composition and a hard-coated plastic lens were obtained in the same manner as in Example 1, except that the amount of ethylenediaminetetraacetic acid iron added was 1.5 parts by mass, and ethylenediaminetetraacetate aluminum and aluminum acetylacetonate were not added. .

<Evaluation of weather resistance and scratch resistance>
(1) Weather resistance evaluation method The weather resistance of the hard-coated plastic lens was evaluated by the following method. That is, using a plastic lens with a hard coat as a sample, the surface of the sample was irradiated with 60 kilolux ultraviolet rays. And the weather resistance of the plastic lens with a hard coat was evaluated by evaluating the adhesiveness of the hard coat film to the plastic lens substrate for the sample before UV irradiation (initial stage) and every irradiation time of 50 hours. In addition, the evaluation of adhesion is to check the degree of peeling of the hard coat film after performing a peeling operation using a cellophane tape by cutting the sample into 25 square grids (1 mm ² / mass) with a cutter. It went by. And the adhesiveness of the sample was determined according to the following criteria.
A: There is no peeling.
○: Slight peeling occurred in a dot shape.
Δ: Peeling less than 10% with respect to the surface area.
X: Peeling of 10% or more with respect to the surface area occurred.

(2) Evaluation method of scratch resistance The scratch resistance of the plastic lens with a hard coat was evaluated by the following two scratch tests.

(I) Scratch test 1
The degree of scratching when the surface of a hard-coated plastic lens was rubbed with steel wool # 0000 was determined according to the following criteria.
(Double-circle): Even if it rubs quite strongly, it is not damaged.
○: Slightly scratched when rubbed considerably.
X: Scratches are observed even with weak friction.

(Ii) Abrasion test 2
Using a plastic lens with a hard coat as a sample, scratch resistance was evaluated by a method based on the Bayer Test method of COLTS Laboratories. That is, both the sample and the uncoated CR39 standard lens were subjected to a vibration test in sand, and the haze of the lens surface after the vibration test was measured. Then, the ratio of the haze of the sample to the haze of the CR39 standard lens (CR39 standard lens haze / sample haze) was calculated, and the determination was made according to the following criteria based on the numerical value of this ratio. A numerical value of this ratio of 1 indicates that the scratch resistance is comparable to that of the CR39 standard lens, and an increase in the numerical value indicates that the scratch resistance of the evaluation lens is increased.
A: The numerical value of the ratio is 2.5 or more.
○: The numerical value of the ratio is 2.0 or more and less than 2.5.
(Triangle | delta): The numerical value of ratio is 1.5 or more, and is less than 2.0.
X: The numerical value of the ratio is less than 1.5.

(3) Evaluation results Table 1 shows the results of evaluating the weather resistance and scratch resistance of the hard-coated plastic lenses obtained in Examples 1 to 6 and Comparative Examples 1 to 3.

  As is clear from the results shown in Table 1, when the coating composition of the present invention was used (Examples 1 to 6), the weather resistance and scratch resistance were sufficiently excellent. On the other hand, when a coating composition containing no iron ethylenediaminetetraacetate was used (Comparative Examples 1 and 2), the adhesion of the hard coat film to the plastic lens substrate after UV irradiation was insufficient, and the weather resistance It was inferior in nature. Further, when a coating composition not containing aluminum acetylacetonate was used (Comparative Example 3), the scratch resistance was inferior.

  As described above, according to the present invention, it has sufficient scratch resistance and is excellent in weather resistance, for example, even when exposed to sunlight for a long period of time, for a high refractive index plastic lens substrate. It is possible to provide a coating composition capable of forming a hard coat film having sufficient adhesion, and a plastic lens using the same.

Claims (6)

(A) titanium oxide-containing composite oxide fine particles;
(B) The following general formula:
R ¹ _a R ² _b Si (OR ³ ) _{4- (a + b)} (1)
(In formula (1), R ¹ represents an organic group having a functional group or an organic group having 4 to 14 carbon atoms having an unsaturated double bond, and R ² represents a hydrocarbon group having 1 to 6 carbon atoms or a halogenated group. A hydrocarbon group, R ³ represents an alkyl group having 1 to 4 carbon atoms, an alkoxyalkyl group or an acyl group, a and b each represent 0 or 1, and a + b represents 1 or 2.
An organosilicon compound represented by the formula:
(C) ethylenediaminetetraacetic acid iron (III);
(D) An acetylacetonate metal whose central metal is at least one metal selected from the group consisting of lithium, copper, zinc, cobalt, nickel, manganese, chromium, zirconium, magnesium, iron, calcium, bismuth, and aluminum A complex compound;
A coating composition comprising:   The coating composition according to claim 1, further comprising (E) aluminum aluminum diaminetetraacetate.   The content of the iron (III) ethylenediaminetetraacetate (C) is an amount that is in the range of 0.5 to 10 parts by mass with respect to 100 parts by mass of the (B) organosilicon compound or its hydrolyzate. The coating composition according to claim 1 or 2, characterized in that   Content of said (D) acetylacetonate metal complex compound is the quantity used as the range which is the range of 0.1-15 mass parts with respect to 100 mass parts of said (B) organosilicon compound or its hydrolyzate. The coating composition according to any one of claims 1 to 3.   Content of said (E) ethylenediaminetetraacetic acid aluminum is the quantity used as the quantity used as the range of 0.5-10 mass parts with respect to 100 mass parts of said (B) organosilicon compound or its hydrolyzate. The coating composition as described in any one of Claims 2-4.   A hard coat film formed from a plastic lens substrate having a refractive index of 1.60 or more and a coating composition according to any one of claims 1 to 5 formed on a surface of the plastic lens substrate. And a plastic lens.