JPH044215A - Plastic lens material and production thereof - Google Patents

Abstract

PURPOSE:To obtain the subject material, having a high refractive index and a low specific gravity and excellent in impact resistance and dyeability by reacting hexamethylene diisocyanate cyclic trimer with a specific diol, a specified acrylic ester, divinylbenzene and an aromatic group-containing monomer. CONSTITUTION:The objective material is obtained by preparing (A) a cyclic trimer of hexamethylene diisocyanate expressed by formula I, (B) a diol compound expressed by formula II (m and n are 0-2), (C) a compound expressed by formula III (Y is H or methyl), (D) a radical-polymerizable compound having an aromatic group and (E) divinylbenzene, bisecting the component (C) into a part for the reaction in the former stage and part for the reaction in the latter stage in the number of mol equal to (alpha-beta) mol when the number of mol of NCO groups in the component (A) is alpha and the number of mol of hydroxyl groups in the component (B) is beta, adding a urethane forming catalyst to the part for reaction in the former stage of the components (A) to (C) and a mixture of the components (D) with (E), carrying out urethane forming reaction, then adding the part for the reaction in the latter stage of the component (C) and a radical polymerization catalyst thereto and performing radical polymerization reaction.

Description

[Detailed Description of the Invention] [Industrial Application Field 2] The present invention relates to a plastic lens material and a method for producing the same, and more specifically, a plastic lens material that has a high refractive index, low specific gravity, high impact strength, and dyeability. The present invention relates to a plastic lens material with excellent adhesion of a first coat and a method for producing the same.

[Prior art]

In modern eyeglass lenses, plastic lenses have various features that cannot be obtained with inorganic glass lenses, such as light weight, safety, and good stainability.
It is becoming widely used.

Materials for eyeglass lenses are desired to have the following properties in a well-balanced manner.

■High refractive index.

■It has a low specific gravity.

■High impact strength.

■Excellent dyeability and hard coat adhesion.

When athletes and the like wear eyeglasses, plastic lens materials for eyeglass lenses are particularly required to be lightweight and have high impact strength from the viewpoint of safety such as protection of the wearer's eyes.

Currently, the most popular plastic lens material is diethylene glycol bisallyl carbonate resin, which has a refractive index of 1.
．． It is relatively low at around 50.

In order to obtain a resin with a high refractive index, it has been proposed to introduce an aromatic unit having a bromine atom into a resin material (for example, JP-A-60-63214).

However, although a high refractive index is achieved by such a method, the specific gravity becomes high and the advantage of light weight is lost.

Furthermore, if the proportion of aromatic structural units is increased in order to obtain a resin with a high refractive index, the impact strength will decrease and the dyeability will also decrease.

On the other hand, in order to obtain resins with high impact strength and excellent dyeing properties, a method has been proposed in which a cyclic trimer derivative of hexamethylene diisocyanate is used as a monomer component (for example, Japanese Patent Laid-Open No. 63-265922 ). but,
Even with this method, it is not possible to obtain sufficiently satisfactory impact strength.

[Problem to be solved by the invention]

Thus, at present, a plastic lens material that has a high refractive index, low specific gravity, high impact strength, and has a well-balanced combination of dyeability and hard coat adhesion has not yet been developed.

The present invention has been made based on the above-mentioned circumstances, and an object of the present invention is to have a high refractive index, low specific gravity, and high impact strength, and to have a balance between dyeability and hard coat adhesion. The object of the present invention is to provide a plastic lens material with good characteristics and a method for manufacturing the same.

[Means to solve the problem]

The plastic lens material of the present invention has the following structural formula (I)
Component A consisting of a cyclic trimer of hexamethylene diisocyanate represented by Component B consisting of a diol compound represented by the following structural formula (II); Component C consisting of a compound represented by the following structural formula (II [)] , D consisting of divinylbenzene, and a radical polymerization-reactive compound having an aromatic group.
The total of component A, component B, component C, divinylbenzene and component D is 100 parts by weight, and the proportion of component A is 5 to 13 parts by weight, and the proportion of component B is lower than that of component A. When the number of moles is a, it is 0.4a to 0.6a mole, and when the proportion of the C component is the number of moles of the A component, it is 9a to 20a.
mole, and the proportion of divinylbenzene is 5 to 20 parts by weight, and is obtained by urethanization reaction and radical polymerization reaction, has a refractive index of 1.58 or more, and has an Izot impact strength (with V notch) of I kg. f −
cm/cm" or more.

Structural formula (I) CH2'''e CH2) 5-NCO Structural formula (II) (m and n are each an integer of 0 to 2.) (Y
represents a hydrogen atom or a methyl group. ) Furthermore, in the method for producing the plastic lens material of the present invention, component A, component B, component C, divinylbenzene, and component D are prepared in the above proportions, and the incyanate group of component A is When the number of moles of the hydroxyl group of component B is α, and the number of moles of the hydroxyl group of component B is β, the number of moles of component C is approximately equal to (α−β) moles). Then, a urethanization catalyst is added to a mixture consisting of component A, component B, the first reaction portion of component C, divinylbenzene, and component D to cause a urethanization reaction,
Thereafter, the method is characterized by including a step of adding a later reaction portion of component C and a radical polymerization catalyst to cause a radical polymerization reaction.

This will be explained in more detail below.

Plastic Lens Material> The plastic lens material according to the present invention comprises a component A consisting of a cyclic trimer of hexamethylene diisocyanate, a component B consisting of a specific diol compound, a specific component C, divinylbenzene, and an aromatic group. A copolymer obtained by subjecting component D, which is a radical polymerization-reactive compound having the following, to a urethanization reaction and a radical polymerization reaction in a specific ratio.

Component A is represented by the above structural formula (I), and its isocyanate group forms a urethane bond with the hydroxyl groups of components B and C to form a bulky structural unit, resulting in a low specific gravity and high durability. A copolymer having a urethane resin structure with excellent impact resistance is obtained.

As component B, which undergoes a urethanization reaction with component A, a diol compound having a specific molecular structure represented by the above structural formula (n) is used, and the resulting copolymer has high impact strength and high refraction. It will have a certain rate.

The longer the molecular chain of the component B compound that constitutes the portion sandwiched between the hydroxyl groups at both ends, the more flexible and high impact strength a copolymer can be obtained.

However, if this molecular chain becomes too long, the aliphaticity will increase and the resulting copolymer will tend to have a low refractive index.

In order to reliably exhibit the above-mentioned effects of component B, it is desirable that all or almost all of the hydroxyl groups at both ends of the molecule of component B bond with the incyanate groups of different molecules of component A.

In the diol compound used as component B),
A copolymer with a large number of bromine atoms and a high refractive index can be obtained, but its specific gravity will be high. However, the difference caused by the number of bromine atoms and the substituted position is not large, and the proportion of this B component used is relatively small, so by selecting an appropriate compound as this B component, the characteristics of the final product can be improved. Can be fine-tuned. Particularly preferable B
A specific example of the component is 2,2-bis[3,5-dibromo-4(2-hydroxyethoxy)phenyldipropane.

The proportion of component A is 5 to 1 when the total of component B, component C, divinylbenzene, and component D is 100 parts by weight.
It is 3 parts by weight. If this proportion is less than 5 parts by weight, it will not be possible to improve impact strength and reduce specific gravity. On the other hand, if this proportion exceeds 13 parts by weight, it will be difficult to achieve a high refractive index, and (This is not preferable because the viscosity of the product becomes very high, which causes problems in its handling, especially in the cast polymerization described below).

The ratio of component B is in the range of 0.4a to 0.6a mol, when the amount of component A used is a mol.

If this ratio is less than 0.4 a mol, the impact strength will be low, and if it exceeds 0.6 a mol, the viscosity of the product after the urethanization reaction will be extremely high.

Component C is represented by the above structural formula (II[), and has a hydroxyl group, a radically polymerizable moiety, and a biphenyl skeleton moiety in the molecule.

A part of the hydroxyl group of component 200 is bonded to the incyanate group of component A by a urethanization reaction, and the radically polymerizable part is bonded to divinylbenzene and component D by a radical polymerization reaction, so this component C completely binds to the incyanate group of component A. The component can be a copolymer with a high degree of crosslinking. The 200 ingredients are
It does not simply have a hydroxyl group and a radically polymerizable moiety,
Since it has a specific molecular structure, the copolymer finally obtained has a high refractive index, excellent dyeability, and excellent hard coat adhesion. In other words, the biphenyl skeleton of component C imparts a high refractive index to the resulting copolymer, and the hydroxyl groups remaining without undergoing a urethanization reaction with the incyanate groups impart excellent dyeability and hard coat adhesion. be done.

Here, the radically polymerizable portion may have an acrylic acid structure or a methacrylic acid structure, or may be a mixture thereof.

Furthermore, as for the biphenyl skeleton part (the part of the phenylphenoxy group), there are isomers of the 2-position, 3-position and 4-position depending on the bonding position of the phenyl group, but in the present invention, any isomer may be used, or a mixture thereof may be used. But that's fine.

The ratio of component C is in the range of 9a to 20a mol, when the amount of component A used is a mol.

When the amount is 9 a mol or more, 0.05 mol or more of hydroxyl groups can remain in 100 g of the copolymer, and therefore a copolymer with high dyeability and hard coat adhesion can be obtained. Therefore, the lower limit of the proportion of C component is
It is defined as the proportion necessary to ensure that the above proportion of hydroxyl groups remains after bonding with all of the isocyanate groups of component A that are not bonded to the hydroxyl groups of component B.

On the other hand, the upper limit of the proportion of component C is determined by considering the required proportions of divinylbenzene and component D.

Divinylbenzene has the role of giving the obtained copolymer a sufficiently crosslinked structure and a high refractive index. By having a sufficiently crosslinked structure, the obtained copolymer has excellent heat resistance, weather resistance, and chemical resistance, and also has sufficient strength.

Even when divinylbenzene is not used, since component A is a trifunctional compound, a certain degree of crosslinked structure is formed, but the degree of crosslinking is insufficient by itself, and divinylbenzene By using this, a high degree of crosslinking can be achieved, and not only high heat resistance, weather resistance, and chemical resistance can be obtained, but also a high refractive index can be achieved.

The proportion of divinylbenzene is 5 to 2 parts by weight when the total of component A, component B, component C, and component D is 100 parts by weight.
It is 0 parts by weight. If this proportion is less than 5 parts by weight, the degree of crosslinking will be insufficient, resulting in poor heat resistance, weather resistance, and chemical resistance. On the other hand, if this proportion exceeds 20 parts by weight, impact strength decreases, which is not preferable.

Component D is a radically polymerizable compound having an aromatic group, and is a compound other than the above-mentioned component C and divinylbenzene. By using this component D, it is possible to adjust the properties of the resulting copolymer, such as its refractive index, impact strength, and specific gravity.

In order to make the copolymer high in refractive index, it is necessary that this D component has at least an aromatic group, while it is preferable that the aliphatic moiety be as small as possible.

In addition, since component D has an aromatic group, component A, B
When combined with component C and divinylbenzene, the copolymer can be made optically homogeneous.

In addition, this component D, together with divinylbenzene, is effective as a solvent in the urethanization reaction. Due to the action of component D as a solvent, excessive increase in the viscosity of the reaction product due to condensation of component A, component B, and part of component C during the urethanization reaction is suppressed, and the reaction product is converted into a liquid state. During the subsequent casting polymerization reaction, ease of pouring into the mold is ensured. From this point of view, it is not preferable to use a compound with a large molecular weight and high viscosity as component D.

Specific examples of preferred component D include styrene, α-methylstyrene, and ethylstyrene.

<Method for Manufacturing Plastic Lens Material> Next, a method for manufacturing the plastic lens material of the present invention will be described.

In this method, component A, component B, component C, divinylbenzene, and component D are each prepared in the specific proportions described above. Then, when the number of moles of the isocyanate group of the component A used is α, and the number of moles of the hydroxyl group of the component B is β, the component C is added to the first reaction portion with a number of moles approximately equal to (α−β) moles, and the part for the second step reaction. It is divided into two parts. Of course, the first stage reaction part and the second stage reaction part may be prepared separately from the beginning.

First, step (I) is performed using each of the above components.

In this step (I), component A, component B, the first reaction portion of component C, divinylbenzene, and component D are mixed, a urethanization catalyst is added to this mixture, and the temperature is adjusted. , a urethane reaction is carried out between the isocyanate group of component A and the hydroxyl group of component B and component C.

In step (I), only the part for the first stage reaction, which is a part of component C, is used. This ensures that all of the B component reacts with the partial molecules of the A component, and as a result, bulky structural units are produced, so the resulting copolymer has a low specific gravity and high impact strength. , unreacted hydroxyl groups of component B are prevented from remaining.

If an excessive amount of component C is used in step (I), for example, the entire amount that should be used, there will be a large excess of hydroxyl groups with respect to the isocyanate groups of component A, so some of the hydroxyl groups of component B will be used as component A. Component B remains unreacted without being bonded to the isocyanate group of component B, and as a result, it may not be possible to sufficiently achieve high impact strength by component B.

The amount of the first reaction portion of component C used in step (I) is approximately equal to the number of moles (α - β) obtained by subtracting the number of moles β of hydroxyl groups in component B from the number α of incyanate groups in component A. The number of moles is γ, and here, “approximately equal to” means that γ is “equal to (α−β) or slightly less than”.

Actually, it is preferable that the value of α/(β+T) is 1.0 to 1.3.

If the value of T is too large, the hydroxyl group of component B remains unreacted as described above, making it impossible to achieve a sufficiently high impact.On the other hand, if the value of T is too small, Because a polymeric substance is produced by the urethanization reaction between component A and component B, the viscosity of the product obtained in step (I) increases, and the reaction in step (2) that is performed subsequently increases. or injection into a mold during cast polymerization.

Examples of the urethanization catalyst used in step (I) include catalysts commonly used in urethanization reactions, such as dibutyltin dilaurate. The amount used is preferably 0.001 to 0.1% by weight based on the reaction mixture to be subjected to the urethanization reaction.

The reaction temperature of the urethanization reaction in step (I) is preferably 5 to 80°C, and the reaction time is preferably 0.5 to 6 hours.

After completion of step (I), step (2) is carried out. In this step (2), the post-reaction portion of component C and a radical polymerization catalyst are added to the product obtained in step (I), the temperature is adjusted, and the post-reaction portion of component C is added to the product obtained in step (I). Divinylbenzene and component D are subjected to a radical polymerization reaction.

Through this radical copolymerization reaction, a copolymer with a high degree of crosslinking in which all the components are integrated can be obtained.

As the radical polymerization catalyst used in this radical copolymerization reaction, catalysts commonly used in radical polymerization reactions, such as lauryl peroxide, can be used. The amount used is preferably 0.5 to 4% by weight based on the reaction mixture j2 consisting of the product obtained in step (I) and the portion for the subsequent reaction of component C.

The reaction temperature is preferably in the range of 20 to 120°C. The reaction temperature may be always constant, but it may also be carried out at a low temperature initially, and then the temperature may be raised stepwise. The reaction time varies depending on temperature conditions, but is preferably about 5 to 36 hours.

In this step (2), since the urethanization reaction catalyst remains in the reaction system, if unreacted isocyanate groups remain in component A, the incyanate groups and the hydroxyl groups of component C form urethane. The remaining incyanate groups of component A are completely consumed, and as a result, the resulting copolymer has no deterioration in weather resistance due to the presence of free incyanate groups. Become.

The reaction in step (2) can be carried out in a normal reactor, or the reaction mixture can be injected into a mold and reacted.
A so-called cast polymerization reaction can also be carried out.

The copolymer obtained by reacting in a reactor is in the form of a block, and when a lens is manufactured from this, cutting and polishing is performed. On the other hand, a cast polymerization reaction is preferable because a desired lens can be directly produced.

In the method of the present invention, when carrying out each step, stabilizers such as oxidation stabilizers, light stabilizers, and thermal stabilizers can be used as necessary within a range that does not inhibit the reaction.

In addition, when obtaining a colored plastic lens material for fashionability or other reasons, the copolymer itself has sufficient coloring properties, so it may be dyed after step (2). However, a pigment or dye can also be added to the reaction mixture when carrying out step [2].

In the method of the present invention, the proportions of catalysts and additives such as stabilizers and pigments are handled as being outside the system depending on the monomer components to be polymerized.

〔Effect of the invention〕

According to the invention of claim 1, it has a high refractive index, low specific gravity, and high impact strength, and has excellent dyeability and hard coat adhesion, and in addition to the above properties, it has the properties required for plastic lens materials. It is possible to provide a plastic lens material that also has other properties in a well-balanced manner.

According to the second aspect of the invention, the plastic lens material described above can be efficiently and advantageously manufactured, and a cast polymerization method suitable for manufacturing plastic lenses can be advantageously applied.

Examples of the present invention will be described below, but the present invention is not limited thereto.

〔Example〕

Regarding the following Examples and Comparative Examples, each characteristic was measured according to the following conditions.

(I) Refractive index The refractive index nW at 25° C. was measured using an Atsube refractometer.

(2) Specific gravity was measured at 25° C. using a specific gravity density meter (manufactured by Toyo Seiki (Ro)).

(3) Impact strength ■Izotsu impact strength test Measured with a V-notch according to JIS K 7110.

■Falling ball destruction test: 16.3g from a height of 1.27m according to US FDA standards
Drop a steel ball onto the fabricated lens, find the number k of broken lenses among the 10 lenses, and calculate the result as /
Displayed in the form of 10.

(4) Dyeability test A plate-shaped sample with a thickness of 1°2 mm was prepared, and its parallel light transmittance was measured using a turbidimeter model 1001 DPJ (manufactured by Nippon Denshoku Kogyo ■). The parallel light transmittance is taken as the parallel light transmittance.Next, this sample is immersed in a 15% aqueous solution of the blue dye "Sumikalon Blue-E-FBLj (manufactured by Sumikagaku Co., Ltd.) at 93°C for 10 minutes, and then taken out, washed with water, and dried. Then, use the same turbidity meter to measure parallel light transmittance.

The difference in parallel light transmittance before and after dyeing was used as a measure of dyeability. The larger this value is, the better the stainability is determined to be.

(5) Hard coat adhesion test After thoroughly cleaning the molded lens with ultrasonic waves using isopropyl alcohol and drying it, apply a silicone resin hard coat agent "TS-56-HJ" (manufactured by Tiyama Soda Co., Ltd.) to the molded lens. It was applied by a dipping method, left to dry at room temperature for 30 minutes, and then heated and cured at 120°C for 2 hours to form a hard coat layer.Next, a 1 cm square area in the center of the hard coated lens was coated. In the test area, cross-cut the hard coat layer with parallel lines vertically and horizontally at 1 mm intervals to form a total of 100 sections, and then paste cellophane adhesive tape on top of the cross-cuts. The tape was peeled off, and the number p of the 100 sections remaining without being peeled off from the lens was calculated, and the result was expressed as p/100.

The larger this value is, the better the adhesion of the hard coat layer is judged to be.

(6) Chemical resistance test Samples were immersed in methanol, acetone, and toluene solvents at room temperature for 6 hours, and then surface changes were observed.

(7) Viscosity Measured using a 7B type viscometer (BM type) (manufactured by Tokyo Keiki Co., Ltd.).

Example 1 Component A cyclic trimer of hexamethylene diisocyanate (incyanate group content 23.1% by weight, effective molecular weight 545 when inocyanate group is the standard of purity)
...8.41 parts by weight Component B 2.2-bis[3,5-dibromo-4-(2-hydroxyethoxy)phenyl]furopane...4.88 parts by weight! !
! 'EC component 1-methacryloquine-3-(2-phenylphenoquine)
-2- Propatool (purity 99.2% by weight)... 46
．． 71 parts by weight divinylbenzene...15.00!1
Part component α-methylstyrene: 25.00 parts by weight Each component was prepared in the above proportions, and 46.71 parts by weight of C component was added to the former reaction part (9.71 parts by weight) and the latter reaction part. (37.0mm part).

In this example, the number of moles of component B is 0.5 times the number of moles of component A, and the number of moles of component C is 9 times the number of moles of component A.
．． It is 63 times more.

Further, the number of moles of the first-stage reaction portion of component C is approximately equal to the number of moles obtained by subtracting the number of moles of hydroxyl groups of component B from the number of moles of insinate groups of component A.

Step (I) Mix the first reaction portion of component C, the above component A, the Bt component, divinylbenzene, and component D, and add dibutyltin dilaurate (urethanization reaction catalyst) to this mixture.
was added at a ratio of 0.01% by weight to the mixture, and 60
The urethanization reaction was carried out at ℃ for 2 hours to obtain a product.

Step (2) The latter reaction portion of component C was added to the product obtained in step (I) and mixed. The viscosity of this mixture was 60 centipoise at 24°C. Add lauryl peroxide (radical polymerization catalyst) to this mixture at a rate of 1.0 to this mixture.
% by weight, poured into a glass mold with a spherical inner surface, and heated at 40°C for 10 hours and at 60°C for 4 hours.
The radical copolymerization reaction was carried out by changing the reaction conditions stepwise at 80° C. for 2 hours and then at 90° C. for 1 hour.

The glass mold was removed to obtain a colorless and transparent concave lens with a center thickness of 1.2 mm and a diameter of 72 mm.

The measurement results of various physical properties of the obtained lens were as follows.

Refractive index n%t: 1.595 Specific gravity: 1.19 Izod impact strength: 1.8 Kg f -cm/c
m2 falling ball destruction test: 0/10 Dyeability = 36% Hard coat adhesion: 100/100 Chemical resistance: No change Example 2 Each component was prepared in the same proportion as Example 1, component A, component B
Component, divinylbenzene, and component D are mixed, and dibutyltin dilaurate (urethanization reaction catalyst) is added to the mixture at a rate of 0. A urethane reaction was carried out at 60° C. for 2 hours to obtain a product.

All of component C was added to the obtained product. The viscosity of this mixture was 230 centipoise at 24°C.

To this mixture, lauryl peroxide (radical polymerization catalyst) was added and mixed at a ratio of 1.0% by weight based on the mixture, and the mixture was poured into a glass mold similar to Example 1, but the viscosity was high. This process took time, and great care was required to prevent air bubbles from entering and to degas before the reaction.

After injection, a radical copolymerization reaction was carried out under the same conditions as in Example 1 to obtain a colorless and transparent concave lens with a center thickness of 1.2 mm and a diameter of 72 mm.

The measurement results of the physical properties of the obtained lens showed similar values except that the Izod impact strength was 1.85 Kg f-cm/cm', which was a slightly higher value than Example 1.

Example 3 Each component was prepared in the same proportion as in Example 1, and component A and component B
Component C, divinylbenzene, and D component were mixed, 0.01% by weight of dibutyltin dilaurate (urethanization reaction catalyst) was added to the mixture, and 6
A urethane reaction was carried out at 0° C. for 2 hours to obtain a product.

The viscosity of this product was 55 centipoise at 24°C.

Lauryl peroxide (radical polymerization catalyst) was added to this product in an amount of 1.0% by weight based on the product, and a radical copolymerization reaction was carried out under the same conditions as in Example 1.
．． After two attempts, a colorless and transparent concave lens with a diameter of 72 mm was obtained.

The results of measuring the physical properties of the obtained lenses showed similar values, except that the Izod impact strength was 1.55 Kg f -cm/cm2, which was a slightly lower value.

Example 4 The proportion of component A was 10.43 parts by weight, and the proportion of component B was 5.
05 weight 1 part, the proportion of divinylbenzene was changed to 10.00 parts by weight, the proportion of component D was changed to 14.00 parts by weight, and 1-acryloxy-3-(2-phenylphenoxy)-2-propanol was added as component C. (Purity 99% by weight) 60.52
Each component was prepared in the same manner as in Example 1 except that parts by weight were used, and 6052 parts by weight of component C was added to the pre-reaction part (
The mixture was divided into a portion for subsequent reaction (48.05 parts by weight) and a portion for subsequent reaction (48.05 parts by weight).

In this example, the number of moles of component B is 0.42 times the number of moles of component A, and the number of moles of component C is 10.5 times the number of moles of component A.

Further, the number of moles of the first-stage reaction portion of component C is approximately equal to the number of moles obtained by subtracting the number of moles of hydroxyl groups of component B from the number of moles of isocyanate groups of component A.

Step (I) Mix the first reaction portion of component C, the above-mentioned component A, component B, divinylbenzene, and component D, and add dibutyltin dilaurate (urethanization reaction catalyst) to this mixture.
was added at a ratio of 0.01% by weight to the mixture, and 60
The urethanization reaction was carried out at ℃ for 2 hours to obtain a product.

Step (2) The latter reaction portion of component C was added to the product obtained in step (I) and mixed. Lauryl peroxide (radical polymerization catalyst) was added to this mixture at a ratio of 1.0% by weight based on the mixture, and the mixture was poured into a glass mold similar to that used in Example 1, and the same reaction as in Example 1 was carried out. A radical copolymerization reaction was carried out under the following conditions to obtain a colorless and transparent concave lens with a center thickness of 1, 2 mm and a diameter of 72 mm.

The measurement results of various physical properties of the obtained lens were as follows.

Refractive index nf: 1.598 Specific gravity: 1.20 Izod impact strength: 1.9 Kg f -cm/c
m' Falling ball destruction test: 0/10 Dyeability: 5% Hard coat adhesion: 100/100 Chemical resistance: No change Example 5 The proportion of A component was 548 parts by weight, the proportion of B component was 3.69
Part by weight, the proportion of component D is 19. ．． Change to 50 parts by weight,
As component C: 1-methacryloxy-3-(4 phenylphenoquine)-2-propatol (99% pure a by weight) 56
．． Each component was prepared in the same manner as in Example 1 except that 1 part of C. ，
51 parts by weight).

In this example, the number of moles of component B is 0.58 times the number of moles of component A, and the number of moles of component C is 17.8 times the number of moles of component A.

Further, the number of moles of the first-stage reaction portion of component C is approximately equal to the number of moles obtained by subtracting the number of moles of hydroxyl groups of component B from the number of moles of isocyanate groups of component A.

Step (I) Mix the first reaction portion of component C, the above-mentioned component A, the Bt component, divinylbenzene, and component D, and add dibutyltin dilaurate (urethanization reaction catalyst) to the mixture. Added at a ratio of 0601% by weight to
The urethane reaction was carried out for 2 hours to obtain a product.

Step (2) The latter reaction portion of component C was added to the product obtained in step (I) and mixed. Lauryl peroxide (radical polymerization catalyst) was added to this mixture at a ratio of 1.0% by weight based on the mixture, and the mixture was poured into a glass mold similar to that used in Example 1, and the same reaction as in Example 1 was carried out. A radical copolymerization reaction was carried out under the following conditions, and the center thickness was 1.2 mm and the diameter was 7 mm.
A colorless and transparent concave lens of 2+11111 was obtained.

The measurement results of various physical properties of the obtained lens were as follows.

Refractive index ng: 1.601 Specific gravity: 1.19 Izod impact strength: l 3 Kg f -cn+/
cm' falling ball fracture test: (]/10 Dyeability: 40% Hard coat adhesion: 100/100 No change in chemical resistance Comparative Example 1 The proportion of component C was reduced to 26.71 parts by weight, and the proportion of component D was Each component was prepared in the same manner as in Example 1, except that the proportion was changed to 45.00 parts by weight by increasing the proportion by the amount equivalent to the reduced amount of component C, and 26.71 parts by weight of component C was added to the pre-reaction part (9 parts by weight). ，
71 parts by weight) and a part for subsequent reaction (7.00 parts by weight).

In this comparative example, the number of moles of component B is 0.50 times the number of moles of component A, and the number of moles of component C is 5.5 times the number of moles of component A.

The first stage reaction part of component C, the component A prepared above,
Component B, divinylbenzene, and component D are mixed, and dibutyltin dilaurate (urethanization reaction catalyst) is added to this mixture at a ratio of 0% by weight to the mixture,
A urethane reaction was carried out at 60° C. for 2 hours to obtain a product.

A portion of component C for subsequent reaction was added to the obtained product. Lauryl peroxide (radical polymerization catalyst) was added to this mixture at a ratio of 1.0% by weight based on the mixture, and the mixture was poured into a glass mold similar to that used in Example 1.
A radical copolymerization reaction was carried out under the same reaction conditions as in Example 1 to obtain a colorless and transparent concave lens with a center thickness of 1.2 mm and a diameter of 72 mm.

When the dyeability of the obtained lens was measured, it was as low as 8%, and the adhesion of the hard coat was 0/100, indicating poor dyeability and adhesion.

Comparative Example 2 The proportion of divinylbenzene was reduced to 3.00 parts by weight, and D
Each component was prepared in the same manner as in Example 1, except that the proportion of the components was changed to 37.0 parts by weight, which was increased by the amount equivalent to the weight loss of divinylbenzene, and the urethanization reaction and A radical copolymerization reaction was carried out to obtain a colorless and transparent concave lens having a center thickness of 1.2 mm and a diameter of 72 mm.

This lens had rubber-like elasticity, but was brittle and easily broke when bent. This is thought to be due to insufficient crosslinking, and the lens was completely unsuitable for use as an eyeglass lens.

Example 6 2,2-bis[4-(2-hydroquinethoquine)phenyl:furopane 2.44 weight 11 was used as the B component, and 1-methacryloquine-3-(4-phenylphenoquine)- was used as the C component. 2-7' lovanol (purity 99% by weight) 4
Each component was prepared in the same manner as in Example 1, except that 9.15 parts by weight was used, and 49.15 parts by weight of component C was added to the former reaction part (9.71 parts by weight) and the latter reaction part ( 39,
44 parts by weight).

In this example, the number of moles of component B is 0.50 times the number of moles of component A, and the number of moles of component C is 10.10 times the number of moles of component A.

Further, the number of moles of the first reaction portion of component C is approximately equal to the number of moles obtained by subtracting the number of moles of hydroxyl group of component B from the number of moles of incyanate groups of component A.

Using each component prepared above, step (I) and step (2) were carried out in the same manner as in Example 1, and the center thickness l,
A colorless and transparent concave lens with a diameter of 72 mm was obtained.

The measurement results of various physical properties of the obtained lens were as follows.

Refractive index n%t: 1.590 Specific gravity: 1.1g Izod impact strength + 1.9 Kg f -cm/c
m” falling ball destruction test: 0/10 Dyeability: 38% Hard coat adhesion: 100/100 Chemical resistance: No change

Claims (1)

[Scope of Claims] 1) A component consisting of a cyclic trimer of hexamethylene diisocyanate represented by the following structural formula (I), a B component consisting of a diol compound represented by the following structural formula (II), and the following structure: Component C consisting of a compound represented by formula (III), divinylbenzene, and D consisting of a radical polymerization-reactive compound having an aromatic group.
The total of component A, component B, component C, divinylbenzene and component D is 100 parts by weight, and the proportion of component A is 5 to 13 parts by weight, and the proportion of component B is lower than that of component A. When the number of moles is a, it is 0.4a to 0.6a mole, and when the proportion of the C component is the number of moles of the A component, it is 9a to 20a.
mole, and the proportion of divinylbenzene is 5 to 20 parts by weight, and is obtained by urethanization reaction and radical polymerization reaction, and has a refractive index of 1.58 or more and an Izod impact strength (with V notch) of 1 kgf. cm/
A plastic lens material comprising a copolymer having a diameter of cm^2 or more. Structural formula (I) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ Structural formula (II) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (m and n are each integers from 0 to 2.) Structural formula (III ) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (Y represents a hydrogen atom or a methyl group.) 2) In the method for manufacturing the plastic lens material according to claim 1, A component, B component, C component,
Divinylbenzene and component D are prepared, and when the number of moles of isocyanate groups in component A is α and the number of moles of hydroxyl groups in component B is β, component C is used in the first stage where the number of moles is approximately equal to (α−β) moles. Divided into a reaction part and a post-reaction part, a urethane-forming catalyst is added to a mixture consisting of component A, component B, first-stage reaction part of component C, divinylbenzene, and component D to convert into urethane. A method for producing a plastic lens material, comprising the steps of causing a reaction, and then adding a portion of component C for a subsequent reaction and a radical polymerization catalyst to cause a radical polymerization reaction.