JP2002069133A - Plastic lens material, method for producing the material, composition for plastic lens, plastic lens obtained by curing the composition and method for producing the plastic lens - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a compound useful as a plastic lens material having high Abbe number of a cured product and relatively small hardening shrinkage, to provide a method for producing the compound, to provide a composition for plastic lens containing the compound, to provide a plastic lens obtained by curing the composition and to provide a method for producing the plastic lens. SOLUTION: The plastic lens material has at least one or more sorts of a group represented by formula (1) as a terminal group and a group represented by formula (2) as a repeating unit [wherein R1 is each independently an allyl group or a methallyl group; A1 and A2 are each independently an organic residue derived from a bivalent carboxylic acid or a carboxylic acid anhydride; X is each independently an organic residue derived from a polyvalence alcohol having 2 or 3 hydroxy groups and an alicyclic structure in a molecule; provided that X may have a branched structure having the group of formula (1) as the terminal group and the group of formula (2) as the repeating unit by an ester bond].

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a plastic lens material, a method for producing the material, a composition for a plastic lens containing the material, a plastic lens obtained by curing the composition, and a method for producing the plastic lens. .

More specifically, it is used for a plastic lens composition capable of suppressing damage to a lens or a mold due to curing shrinkage, which is a problem in polymerization of a polyethylene glycol poly (allyl carbonate) -based plastic lens material. The present invention relates to a possible plastic lens material, a method for producing the material, a composition for a plastic lens containing the material, a plastic lens obtained by curing the composition, and a method for producing the plastic lens.

[0003]

2. Description of the Related Art In recent years, organic glass has been widely used for optical materials, for example, cameras, televisions, prisms, telescopes, and spectacle lenses. In particular, as for spectacle lenses, the replacement of inorganic glass with organic glass, especially plastic lenses, is in progress. Under these circumstances, plastic lenses are required to have characteristics such as lighter weight and easier molding than ever before.

A typical example of a resin conventionally used as a raw material for a plastic lens is a polystyrene resin.
Examples thereof include a polycarbonate resin, a polymethyl methacrylate resin, and a polydiethylene glycol bis (allyl carbonate) resin. The physical properties and production methods of these resins have been known for some time, and are described in detail in, for example, Plastic Age (Vol 35, pp. 198-202 (1989)).

[0005] Among them, the features of plastic lenses derived from each resin are described as follows. For plastic lenses derived from polystyrene resin,
Although it has a high refractive index, it is said that there is a drawback that sufficient values are not obtained in terms of birefringence and light scattering. Further, it has been pointed out that a plastic lens derived from a polycarbonate resin has a high impact resistance, but is inferior in solvent resistance, scratch resistance and the like. Furthermore, it is described that a plastic lens derived from a polymethyl methacrylate resin has a low refractive index and does not have a satisfactory level of impact resistance.

On the other hand, plastic lenses derived from polydiethylene glycol bis (allyl carbonate) resin are known (for example, European Patent Application Publication No. 04).
No. 73163), this plastic lens has a low refractive index of 1.498, but has excellent characteristics such as excellent impact resistance and a high Abbe number, and is particularly advantageous as a plastic lens for spectacles. Many are used.

Further, since the polymerization reaction of polydiethylene glycol bis (allyl carbonate) resin is slower than that of acrylic resin, the polymerization reaction can be easily controlled. Therefore, a uniform polymerization reaction is possible, and a plastic lens derived from polydiethylene glycol bis (allyl carbonate) resin has an advantage that optical distortion is small.

Further, regarding the dyeability of a plastic lens derived from polydiethylene glycol bis (allyl carbonate) resin, when a plastic lens obtained by a casting method is dyed by a general method of applying a dye solution at a high temperature, It is known that the dyeing density is superior to plastic lenses derived from other resins.

Generally, a plastic lens is
It is made by so-called cast polymerization, in which monomers are polymerized between two glass molds. The mold must be washed after casting, and such washing is usually performed using a strong alkaline solution or strong acid. Glass is preferably used because, unlike metal, it is difficult to deteriorate by washing. Furthermore, the glass is easily polished and can have very low surface roughness.

Generally, the polymerization process involves curing shrinkage. However, the lens must completely shape the curve of the glass surface. This requires good adhesion of the monomer to the glass during polymerization.

However, if the curing shrinkage is too high, the lens may be cracked when the curing speed is increased, or the lens or the mold may be damaged when the lens is peeled off from the mold. This is a phenomenon that occurs randomly in the manufacture of lenses. Usually, for plastic lenses derived from polyethylene glycol bis (allyl carbonate) resin, this phenomenon affects a few percent of plastic lens production.

[0012]

DISCLOSURE OF THE INVENTION The present invention provides a compound useful as a plastic lens material having a high Abbe number of a cured product and relatively small curing shrinkage, a method for producing the compound, and a compound containing the compound. An object of the present invention is to provide a composition for a plastic lens, a plastic lens obtained by curing the composition, and a method for producing the plastic lens.

[0013]

Means for Solving the Problems The present inventors have intensively studied to solve the above problems. As a result, it has been found that the use of a (meth) allyl ester-based compound containing an alicyclic structure can provide a plastic lens material having a high Abbe number of a cured product and relatively small curing shrinkage, and completed the present invention. It led to.

That is, the present invention (I) has the following general formula (1)
Is a plastic lens material having at least one or more groups represented by the following formulas as a terminal group, and having a group represented by the following general formula (2) as a repeating unit. General formula (1)

[0015]

Embedded image

(Wherein, R ¹ each independently represents an allyl group or a methallyl group, and A ¹ each independently represents an organic residue derived from a divalent carboxylic acid or carboxylic anhydride. ) General formula (2)

[0017]

Embedded image

(Wherein A ² each independently represents an organic residue derived from a divalent carboxylic acid or a carboxylic anhydride, X represents each independently 2 to 3 hydroxyl groups and Represents an organic residue derived from a polyhydric alcohol having a cyclic structure in the molecule, wherein X is an ester bond, and the above-mentioned general formula (1) is a terminal group; Can be provided.)

Further, the present invention (II) can be carried out in the presence of a catalyst.
At least one or more selected from the following general formula (4);
The present invention (I) comprising a step of performing a transesterification reaction with the polyhydric alcohol according to claim 1 or 2 to obtain a plastic lens material.
And a method for producing the material. General formula (4)

[0020]

Embedded image

(Wherein A represents an organic residue derived from a divalent carboxylic acid or carboxylic acid anhydride,
R ⁴ and R ⁵ each independently represent either an allyl group or a methallyl group. )

Further, the present invention (III) relates to a composition for a plastic lens, which comprises at least one of the materials of the present invention (I).

The present invention (IV) further relates to the present invention (II)
A plastic lens composition comprising at least one kind of radical polymerization initiator in an amount of 0.1 part by mass to 10 parts by mass based on 100 parts by mass of the plastic lens composition of I).

Further, the present invention (V) relates to the present invention (II)
It is a plastic lens obtained by curing the composition for plastic lens of I) or the present invention (IV).

Further, the present invention (VI) is a compound of the present invention (V)
Is a method of manufacturing a plastic lens.

[0026]

BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, the present invention will be described in more detail.

First, the material of the present invention (I) will be described. The present invention (I) is a plastic lens material having at least one or more of groups represented by the following general formula (1) as a terminal group and having a group represented by the following general formula (2) as a repeating unit. . General formula (1)

[0028]

Embedded image

(Wherein, R ¹ each independently represents an allyl group or a methallyl group, and A ¹ each independently represents an organic residue derived from a divalent carboxylic acid or carboxylic anhydride. ) General formula (2)

[0030]

Embedded image

(Wherein A ² each independently represents an organic residue derived from a divalent carboxylic acid or carboxylic anhydride, X represents each independently 2 to 3 hydroxyl groups and Represents an organic residue derived from a polyhydric alcohol having a cyclic structure in the molecule, wherein X is an ester bond, and the above-mentioned general formula (1) is a terminal group; Can be provided.)

In the general formula (1), R ¹ each independently represents either an allyl group or a methallyl group. In the general formula (1), A ¹ is each independently:
It represents an organic residue derived from a divalent carboxylic acid or carboxylic anhydride. In the general formula (2), A ²
Each independently represents an organic residue derived from a divalent carboxylic acid or carboxylic anhydride. Further, in the general formula (2), X independently represents an organic residue derived from a polyhydric alcohol having 2 to 3 hydroxyl groups and having an alicyclic structure in the molecule.

As used herein, "each R ¹ is independently" means that all the moieties represented by R ¹ in the terminal group represented by the general formula (1) in the material of the present invention (I) are allyl. Group, a methallyl group, or a part thereof may be an allyl group and the other part may be a methallyl group.

A ¹ in the general formula (1) and A ² in the general formula (2) represent an organic residue derived from a divalent carboxylic acid or carboxylic anhydride. As the “divalent carboxylic acid or carboxylic anhydride” here, the following compounds can be exemplified.

Aliphatic dicarboxylic acids or anhydrides such as succinic acid or its anhydride, glutaric acid or its anhydride, adipic acid, malonic acid or its anhydride, 2-methylsuccinic acid or its anhydride, 1,
4-cyclohexanedicarboxylic acid, 1,3-cyclohexanedicarboxylic acid, 1,2-cyclohexanedicarboxylic acid or its acid anhydride, 4-methylcyclohexane-
Examples include dicarboxylic acids having an alicyclic structure such as 1,2-dicarboxylic acid or acid anhydride thereof or anhydride thereof, and aromatic dicarboxylic acids such as terephthalic acid, isophthalic acid, phthalic acid or anhydride thereof or anhydride thereof. be able to. However, it goes without saying that the present invention is not limited to these specific examples.

In the above, from the viewpoint of the fluidity of the compound,
Particularly preferred are glutaric acid, succinic acid, adipic acid, 2-methylsuccinic acid and 1,3-cyclohexanedicarboxylic acid, and particularly preferred are glutaric acid, 2-methylsuccinic acid, adipic acid and succinic acid.

The expression “A ¹ is independently of each other” or “A ² is independently of each other” is used in the present invention (I)
A portion represented by A ¹ in the terminal group represented by the general formula (1) in the material of the formula (I) and A ² of a repeating unit represented by the general formula (2) in the material of the present invention (I) Part (hereinafter,
“A ¹ ” and “A ² ” are collectively expressed as “A”. ) Are all organic residues derived from a divalent carboxylic acid or carboxylic anhydride having the same alicyclic structure, but all have an alicyclic structure having a different alicyclic structure.
Organic residues derived from divalent carboxylic acids or carboxylic acid anhydrides, or organic residues partially derived from divalent carboxylic acids having an alicyclic structure having the same structure as other residues. May be an organic residue derived from a divalent carboxylic acid having an alicyclic structure having a different structure.

That is, in the following structural formula (16), which is an example of the material of the present invention (I), it means that each of k A's contained in the repeating structure is independent. Structural formula (16)

[0039]

Embedded image

(In the structural formula (16), A independently represents an organic residue derived from a divalent carboxylic acid, k represents an integer of 2 to 3. X represents 2 to 3 Represents an organic residue derived from a polyhydric alcohol having one hydroxyl group and having an alicyclic structure in the molecule.)

For example, k A in the structural formula (16)
Is an organic residue derived from a divalent carboxylic acid having all different alicyclic structures (that is, one organic residue derived from a divalent carboxylic acid having k kinds of alicyclic structures)
Organic residues each derived from a divalent carboxylic acid having the same alicyclic structure (that is, derived from a divalent carboxylic acid having one kind of alicyclic structure). Or k of A), some of the A are organic residues derived from divalent carboxylic acids having the same alicyclic structure, and some of the others are different. Or a mixed structure such as an organic residue derived from a divalent carboxylic acid having an alicyclic structure.

Further, "X is independently of each other" herein means that in the following structural formula (17) which is an example of a repeating unit represented by the general formula (2), m X is independent of each other.

Structural formula (17)

[0044]

Embedded image

(In the structural formula (17), X independently represents an organic residue derived from a polyhydric alcohol having 2 to 3 hydroxyl groups and having an alicyclic structure in the molecule; Represents an integer of 0 or 1 or more, and when m is an integer of 1 or more, n represents 0 or an integer of 1 or more;
Are each independently an organic residue derived from a divalent carboxylic acid. )

For example, m Xs in the structural formula (17)
Are all derived from the same polyhydric alcohol, even if they are organic residues derived from different polyhydric alcohols (ie, one organic residue derived from m kinds of polyhydric alcohols). Organic residues (ie, m organic residues derived from one kind of polyhydric alcohol)
Alternatively, a mixed structure in which some of the m Xs are organic residues derived from the same polyhydric alcohol and some others are organic residues derived from another type of polyhydric alcohol. No problem. Further, the mixed structure may be entirely random or partially repeated.

Further, X can have a branched structure in which general formula (1) is a terminal group and general formula (2) is a repeating unit by an ester bond. That is,
For example, when X has an organic residue derived from cyclohexane-1,2,4-trimethanol, which is an example of a trivalent saturated alcohol, the material of the present invention (I) is represented by the following structural formula (18). Can be provided. Structural formula (18)

[0048]

Embedded image

Of course, X is an organic residue derived from a polyhydric alcohol having 2 to 3 hydroxyl groups independently and having an alicyclic structure in the molecule. A is
Each is independently an organic residue derived from a divalent carboxylic acid.

X in the general formula (2) independently represents an organic residue derived from a polyhydric alcohol having 2 to 3 hydroxyl groups and having an alicyclic structure in the molecule. Examples of the “polyhydric alcohol having two to three hydroxyl groups and having an alicyclic structure in the molecule” include the following. However, it goes without saying that the present invention is not limited to these specific examples.

Structural formula (1)

Embedded image

Structural formula (2)

Embedded image

Structural formula (3)

Embedded image

Structural formula (4)

Embedded image

Structural formula (5)

Embedded image

Structural formula (6)

Embedded image

Structural formula (7)

Embedded image Further, a dihydric alcohol represented by the following general formula (3) may be used.

General formula (3)

Embedded image

[0059] (wherein, R ² represents at least one selected from organic groups represented by each independently represent the following structural formula (8) to the following structural formula (10), R ³ are each independently Represents at least one selected from the following structural formulas (11) to (13), wherein a and b each independently represent an integer of 0 or 1 to 10, and Y represents the following structural formula ( 14) or any organic group selected from the following structural formula (15):

Structural formula (8)

Embedded image

Structural formula (9)

Embedded image

Structural formula (10)

Embedded image

Structural formula (11)

Embedded image

Structural formula (12)

Embedded image

Structural formula (13)

Embedded image

Structural formula (14)

Embedded image

Structural formula (15)

Embedded image

In the general formula (3), “R ² independently of each other” means that even if all a ² R ² have an organic group having the same structure, all of R ² have an organic group having a different structure. Even
Further, it means that some may be organic groups having the same structure and other parts may be organic groups having different structures. Where R
² needs to be selected from the organic groups represented by the structural formulas (8) to (10).

In the general formula (3), “R ³ is each independently” means that even when all of b R ³ have an organic group of the same structure, all of the organic groups of different structures are present. However, it also means that some may be organic groups having the same structure and other parts may be organic groups having different structures. However, R ³ needs to be selected from the organic groups represented by the structural formulas (11) to (13).

Further, in the general formula (3), a and b each independently represent 0 or an integer of 1 to 10.

Further, Y represents any one of the organic groups selected from the following structural formulas (14) and (15).

Specific examples of the dihydric alcohol represented by the general formula (3) include 2,2-bis [4- (2-hydroxyethoxy) cyclohexyl] propane and 2,2-bis [4- (2 -Hydroxypropoxy) cyclohexyl]
Propane, 3 mol ethylene oxide adduct of 2,2-bis (4-hydroxycyclohexyl) propane,
4 mol of (4-hydroxycyclohexyl) propane
Propylene oxide adduct, bis [4- (2-hydroxyethoxy) cyclohexyl] methane, bis [4-
(2-hydroxypropoxy) cyclohexyl] methane and bis (4-hydroxycyclohexyl) methane
mol ethylene oxide adduct, 4 mol propylene oxide adduct of bis (4-hydroxycyclohexyl) methane, and the like. However, it goes without saying that the present invention is not limited to these specific examples.

Among the above-mentioned polyhydric alcohols, the compounds represented by the structural formulas (1) and (2)
A compound of structural formula (3), 2,2-bis [4-
(2-hydroxyethoxy) cyclohexyl] propane, 2,2-bis [4- (2-hydroxypropoxy)
[Cyclohexyl] propane and 3 mol ethylene oxide adduct of 2,2-bis (4-hydroxycyclohexyl) propane are preferably used. More preferably, structural formula (1), 2,2-bis [4- (2-hydroxyethoxy) cyclohexyl] propane, 2,2-bis [4- (2-hydroxypropoxy) cyclohexyl]
It is a 3 mol ethylene oxide adduct of propane and 2,2-bis (4-hydroxycyclohexyl) propane.

There are no particular restrictions on the number of repetitions of the group represented by the general formula (2), which is a repeating unit of the material of the present invention (I). Materials having various repetition times may be mixed and used. Further, there is no problem in using the material having the number of repetitions of 0 in combination with the material having the number of repetitions of 1 or an integer. However, the number of repetitions is 0
It is not preferable to use only the compound which is in order to achieve the object of the present invention.

The number of repetitions of the group represented by formula (2), which is a repeating unit of the material of the present invention (I), is usually from 0 to
It is preferably an integer of 50. Repeat count is 50
When a plastic lens material consisting only of a compound exceeding the above is used in the composition for a plastic lens, the concentration of allyl groups is low, so that curing may be delayed during curing or some of the compound may remain uncured and cure. This is unfavorable because it may affect physical properties such as mechanical properties of the product. Preferably, the number of repetitions of all compounds in the plastic lens material is an integer in the range of 0 to 50, more preferably an integer in the range of 0 to 30, and even more preferably an integer in the range of 0 to 10. .

In the material of the present invention (I), the compound represented by the general formula (4), which is a raw material, may remain depending on the production conditions, but it may be used as it is as a plastic lens material. Absent. However, when the present invention (I) is used as a plastic lens material,
The fact that the compound represented by the general formula (4) is present in an amount of 90% by mass or more with respect to all the curable components is not preferable in order to reduce the curing shrinkage.

The “total curable component” described in the present specification means the total amount of the material of the present invention (I) and a monomer copolymerizable with at least one of the materials of the present invention (I). .

Next, the present invention (II) will be described. The present invention (II) is characterized by including a step of performing a transesterification reaction of at least one selected from the following general formula (4) with a polyhydric alcohol in the presence of a catalyst to obtain a compound for a plastic lens material. And a method for producing the material of the present invention (I).

Formula (4)

Embedded image

(Where A represents an organic residue derived from a divalent carboxylic acid or carboxylic anhydride,
R ⁴ and R ⁵ each independently represent either an allyl group or a methallyl group. )

In the general formula (4), R ⁴ and R ⁵ each independently represent either an allyl group or a methallyl group.

A in the general formula (4) represents an organic residue derived from a divalent carboxylic acid or carboxylic anhydride. As used herein, “divalent carboxylic acid or carboxylic anhydride” includes succinic acid or its anhydride, glutaric acid or its anhydride, adipic acid, malonic acid or its anhydride, 2-methylsuccinic acid or Aliphatic dicarboxylic acids such as acid anhydrides or anhydrides thereof, 1,4-cyclohexanedicarboxylic acid, 1,3
Dicarboxylic acid having an alicyclic structure such as -cyclohexanedicarboxylic acid, 1,2-cyclohexanedicarboxylic acid or an acid anhydride thereof, 4-methylcyclohexane-1,2-dicarboxylic acid or an acid anhydride thereof or an anhydride thereof, terephthalic acid Examples thereof include aromatic dicarboxylic acids such as acid, isophthalic acid, phthalic acid and anhydride thereof and anhydrides thereof, but needless to say, the present invention is not limited to these specific examples.

The compound of the present invention (I) can be produced, for example, by the following method.

At least one of the compounds represented by the general formula (4) is used in a fixed ratio, and these compounds and a compound having two to three hydroxyl groups and an alicyclic structure in the molecule are used. The target compound can be obtained by a step of performing a transesterification reaction with at least one or more of the polyols in the presence of a catalyst. Of course, the present invention is not limited to this, and a process such as purification may be performed if necessary.

The catalyst used in the above step is not particularly limited as long as it can be generally used in a transesterification reaction. Organic metal compounds are particularly preferred, specifically tetraisopropoxytitanium, tetrabutoxytitanium, dibutyltin oxide, dioctyltin oxide,
Examples include, but are not limited to, acetylacetone hafnium, acetylacetone zirconium, and the like. Among them, dibutyltin oxide and dioctyltin oxide are preferred.

The reaction temperature in this step is not particularly limited, but is preferably in the range of 100 ° C. to 230 ° C., more preferably in the range of 120 ° C. to 200 ° C. In particular, when a solvent is used, it may be restricted by its boiling point.

In this step, a solvent is not usually used, but a solvent can be used if necessary. The solvent that can be used is not particularly limited as long as it does not inhibit the transesterification reaction. Specific examples include, but are not limited to, benzene, toluene, xylene, and cyclohexane. Of these, benzene and toluene are preferred. However, it is also possible to carry out without using a solvent as described above.

Next, the present invention (III) or the present invention (I
The composition for a plastic lens V) will be described.

The present invention (III) is a composition for a plastic lens comprising at least one compound of the present invention (I).

The present invention (I) with respect to all the curable components contained in the plastic lens composition of the present invention (III)
Is preferably from 5% by mass to 80% by mass, and more preferably from 15% by mass to 70% by mass. If the amount of the material is less than 5% by mass, it is difficult to satisfy both the high Abbe number and the low curing shrinkage properties, which is not preferable.

On the other hand, in the present invention (III), a compound copolymerizable with the compound of the present invention (I) is contained in the plastic lens composition of the present invention mainly for the purpose of adjusting the viscosity of the composition. One or more kinds can be added within a range not exceeding 20% by mass based on the total curable components to be prepared.

Examples of the compound include a monomer having an acryl group, a vinyl group and an allyl group. As specific examples, methyl (meth) acrylate, isobornyl (meth) acrylate, and the like can be given as monomers having an acryl group, and vinyl acetate, vinyl benzoate, and the like can be given as monomers having a vinyl group. Further, examples of the monomer having an allyl group include compounds having the following structural formulas (19) to (25). Furthermore, the product name CR-39 manufactured by PPG
(Registered trademark), polyethylene glycol bis (allyl carbonate) resin. Of course, it is not limited to these specific examples, diallyl phthalate, diallyl terephthalate, as long as the physical properties of the plastic lens obtained by curing are not impaired.
It is also possible to use diallyl isophthalate, allyl benzoate and the like.

Among the compounds, specific examples which are preferably used are compounds represented by the structural formulas (19) to (25) and polyethylene glycol bis (allyl carbonate) resin.

Structural formula (19)

Embedded image

Structural formula (20)

Embedded image

Structural formula (21)

Embedded image

Structural formula (22)

Embedded image

Structural formula (23)

Embedded image

Structural formula (24)

Embedded image

Structural formula (25)

Embedded image

The amount of the compound varies greatly depending on which monomer is used, but is generally 90% by mass or less based on the total curable components contained in the plastic lens composition of the present invention. , Preferably 80% by mass or less, more preferably 75% by mass or less. If the content exceeds 90% by mass, it is difficult to satisfy both the high Abbe number and the low curing shrinkage required for the plastic lens of the present invention.

As another effect, by adding 0.5% by mass or more of the plastic lens material (I) of the present invention to a polyethylene glycol bis (allyl carbonate) resin, the polyethylene glycol bis (allyl carbonate) resin Can be improved.

Further, the most suitable monomer is selected according to the kind and the mixing ratio of the above-mentioned and allyl ester oligomers contained in the resin composition for a plastic lens, and the physical properties such as the optical properties required of the plastic lens obtained by curing. .

The viscosity of the plastic lens composition of the present invention (III) is 25 ° C. in consideration of the workability of casting.
Is generally 3000 mPa · s or less, preferably 1000 mPa · s or less, more preferably 500 mPa · s or less.

The term "viscosity" as used herein refers to a value measured by a rotational viscometer. For details of the rotational viscometer, see Iwanami Physical and Chemical Dictionary, 3rd edition, June 1, 1977, 3rd edition, 8th edition.
There is a description in the printing issue.

Further, the present invention (IV) is a compound of the present invention (II)
A plastic lens composition comprising at least one kind of radical polymerization initiator in an amount of 0.1 part by mass to 10 parts by mass based on 100 parts by mass of the plastic lens composition of I).

It is possible and preferable to add a radical polymerization initiator as a curing agent to the plastic lens composition of the present invention (IV).

The radical polymerization initiator that can be added to the plastic lens composition of the present invention (IV) is not particularly limited. Known ones may be used as long as they do not adversely affect physical properties such as optical properties of the plastic lens obtained by curing.

However, the radical polymerization initiators used in the present invention are those which are soluble in other components present in the composition to be cured and which generate free radicals at 30 ° C. to 120 ° C. desirable. Specific examples of the radical polymerization initiator that can be added include diisopropyl peroxy dicarbonate, dicyclohexyl peroxy dicarbonate, di-n-propyl peroxy dicarbonate, di-
Examples include, but are not limited to, sec-butyl peroxydicarbonate, t-butyl perbenzoate, and the like. From the viewpoint of curability, diisopropyl peroxydicarbonate is preferred.

The radical polymerization initiator is added in an amount of 0.1 to 10 parts by mass based on 100 parts by mass of the total curable components contained in the plastic lens composition of the present invention (III).
It is in the range of parts by mass, preferably in the range of 1 part by mass to 5 parts by mass. If the amount is less than 0.1 part by mass, the composition may be insufficiently cured. It is economically undesirable to add more than 10 parts by mass.

The composition for a plastic lens of the present invention (III) or (IV) includes a coloring agent such as a general dye or pigment used for improving the performance of a plastic lens.
Additives such as an ultraviolet absorber, a release agent and an antioxidant may be added.

Examples of the coloring agent include organic pigments such as anthraquinone type, azo type, carbonium type, quinoline type, quinone imine type, indigoid type and phthalocyanine type; organic dyes such as azoic dyes and sulfur dyes; Inorganic pigments such as iron, zinc yellow, chrome orange, molybdenum red, cobalt violet, cobalt blue, cobalt green, chromium oxide, titanium oxide, zinc sulfide, and carbon black.

Examples of the release agent include stearic acid, butyl stearate, zinc stearate, stearamide,
Fluorine compounds, silicon compounds and the like can be mentioned.

Examples of the ultraviolet absorber include triazoles such as 2- (2'-hydroxy-tert-butylphenyl) benzotriazole, benzophenones such as 2,4-dihydroxybenzophenone, 4-tert-butylphenyl salicylate and the like. Salicylates, bis-
(2,2,6,6-tetramethyl-4-piperidinyl)
Hindered amines such as Seva sheet.

Examples of antioxidants include 2,6-di-ter
t-butyl-4-methylphenol, tetrakis- [methylene-3- (3 ', 5'-di-tert-butyl-4-
[Hydroxyphenyl) propionate], phenols such as methane, sulfurs such as dilauryl-3,3'-thiodiproonate, and phosphorus-based antioxidants such as trisnonylphenylphosphite.

Colorants such as dyes and pigments, ultraviolet absorbers,
The total amount of additives such as a release agent and an antioxidant is desirably 1% by mass or less based on all the curable resin components contained in the plastic lens resin composition of the present invention.

Next, the present invention (V) will be described. The present invention (V) is a plastic lens obtained by curing the plastic lens composition of the present invention (III) or (IV).

The curing shrinkage of the plastic lens of the present invention is preferably not more than 10.0% at 23 ° C. The reason is that if the curing shrinkage is too large when cured, cracks are likely to occur during curing, and as a result, the yield during molding will be reduced.

Finally, the present invention (VI) will be described.
The present invention (VI) is the present invention (III) or the present invention (I
This is a method for producing the plastic lens of the present invention (V) obtained by curing the composition for a plastic lens of V).

Cast molding is suitable for the molding method of the plastic lens composition of the present invention. Specifically, a method of adding a radical polymerization initiator to the composition, injecting it through a line into a mold immobilized with an elastomer gasket or a spacer, and molding the composition by a method of curing by heat in an oven or the like. And the like.

At this time, the material used as the mold is metal or glass. Generally, plastic lens molds must be cleaned after casting, and such cleaning is usually performed using a strong alkaline solution or strong acid. Glass, unlike metal, is preferably used because it is not easily deteriorated by cleaning, is easily polished, and has a very low surface roughness.

Since the plastic lens composition of the present invention (III) or (IV) has an alicyclic structure, polydiethylene glycol bis (allyl), which is often used in plastic lenses, depends on the molecular design. The refractive index of a plastic lens made of (carbonate) as a raw material can be easily approached to 1.498. Therefore,
There is also an advantage that a conventionally used product can be used as it is without changing a mold or the like used for molding.

The curing temperature during molding is about 30 ° C. to 120 ° C.
° C, preferably 40 ° C to 100 ° C. Regarding the operation of the curing temperature, in consideration of shrinkage and distortion during curing, a method of gradually curing while raising the temperature is preferable, and is generally 0.5 to 100 hours, preferably 3 to 5 hours.
The curing is preferably performed for 0 hours, more preferably for 10 hours to 30 hours.

The method for dyeing a plastic lens of the present invention is not particularly limited. Any known dyeing method for plastic lenses may be used. Among them, the immersion dyeing method conventionally known as a general method is preferable. The “immersion dyeing method” here is a method in which a disperse dye is dispersed in water together with a surfactant to prepare a dyeing solution, and a plastic lens is immersed in the dyeing solution and dyed under heating.

The method of dyeing a plastic lens is not limited to the immersion dyeing method, but other known methods, for example, a method of dyeing a plastic lens by sublimating an organic pigment (Japanese Patent Publication No. 35-1384), a method of sublimation Method for dyeing plastic lenses by sublimating a sexual dye (Japanese Patent Publication Sho 56
-159376, Japanese Patent Publication No. 1-277814) can also be used. The immersion dyeing method is most preferable because the operation is simple.

[0126]

EXAMPLES The present invention will be described in detail below with reference to examples, but the present invention is not limited to these examples.

The measurement of various physical properties was carried out as follows. 1. Refractive index (n _D ) and Abbe number (ν _D ) A test piece having a size of 9 mm × 16 mm × 4 mm was prepared, and the refractive index (n _D ) at 25 ° C. and the Abbe number were measured using an Abago “Abbe refractometer 1T” The number (ν _D ) was measured. The contact liquid used was α-bromonaphthalene. 2. Viscosity Example 1, Example 3 to Example 6, Example 8 to Example 1
5. For Comparative Examples 1 to 5, the measurement temperature was 25 ° C.
No. was measured using a B-type viscometer (model BH type) manufactured by Tokyo Keiki Co., Ltd. Using one rotor, 300 g of a sample was put into a 300 ml tall beaker, and the measurement was performed at a rotation speed of 20 rpm. For Example 2 and Example 7, the measurement temperature was 25
At ℃, Tokyo Keiki Co., Ltd. type B viscometer (model B8U type)
Was measured using an HH-1 rotor and a sample of 5.2 ml in a designated container at a rotation speed of 100 rpm.

[0128] 3. It was measured according to JIS K 6911 using Barcol hardness 934-1. 4. Measurement of Curing Shrinkage The value of the curing shrinkage (%) was calculated from the specific gravity of the composition before curing and the specific gravity of the cured product using the following formula. Curing shrinkage (%) = (1− (specific gravity of composition before curing / specific gravity of cured product)) × 100 At this time, the specific gravity of the composition before curing is determined by a specific gravity measuring method using a specific gravity bottle at a measurement temperature of 23 ° C. (See JIS Z 8804)
Was measured by Further, the specific gravity of the cured product after curing was measured by a float-sink method (23 ° C.) (see JIS K7112).

[0129] 5. Dyeing method and evaluation of uneven dyeing 0.8 g of Sumicaron Blue E was placed in a 1-liter beaker.
-FBL (Sumitomo Chemical Co., Ltd.) and 0.5 liter of water were added and dissolved by stirring. This was heated in a water bath at 80 ° C., and the cured plastic lens sample was attached to a holder so as not to overlap with the disperse dye solution, immersed at 80 ° C. for 10 minutes, and then taken out. After sufficiently washing with water, it was dried with hot air in an oven at 30 ° C. The obtained dyed plastic lens sample was visually inspected, and a sample in which uneven dyeing was observed without being uniformly dyed in appearance was regarded as defective. The total number of cured samples was 30 and the number of defective samples was counted.

(Production Example-1) 500 m with distillation apparatus
160.2 g of dimethyl glutarate in a three-necked flask
Allyl alcohol 232.3 g, potassium acetate 0.27
g, 1.33 g of calcium hydroxide (1% by mass with respect to dimethyl glutarate), and a bath temperature of 11 under a nitrogen stream.
Methanol produced by heating at 0 ° C to 120 ° C was distilled off. The reaction was continued until the theoretical amount of methanol was distilled off. When 64 g (100% of the theoretical methanol distilled amount) had been distilled off, the reactor was cooled. The obtained reaction solution was purified by distillation under reduced pressure, and 200 g of diallyl glutarate as a colorless and transparent liquid (isolated yield: 95%, raw material: 1 mo)
l) obtained.

In a 300 ml three-necked flask equipped with a distillation apparatus, 101 g (0.48 mol) of diallyl glutarate,
53.8 g of 1,4-cyclohexanedimethanol (0.
373 mol) and 0.1 g of dibutyltin oxide (1% by mass based on diallyl glutarate) and heated at 180 ° C. in a nitrogen stream to distill off allyl alcohol produced. When about 26 g of allyl alcohol was distilled off, the pressure in the reaction system was reduced to 1.33 kPa, and the distillation rate of allyl alcohol was increased. Theoretical amount (43.6
g) After distilling off the allyl alcohol, the mixture was further heated for 1 hour and kept at 190 ° C.-0.13 kPa for 1 hour.
The reactor was cooled to obtain 110 g of an allyl ester compound (hereinafter, referred to as “sample A”). 400 MHz ¹ H-NMR spectrum of the obtained sample A (solvent:
CDCl ₃ ) and FT-IR spectra are shown in FIGS. 1 and 2, respectively.

In FIG. 1, the peak around 0.9 ppm to 2.0 ppm is for a proton derived from a cyclohexane ring, the peak around 2.3 ppm to 2.5 ppm is for a proton derived from a glutaric acid skeleton, 3.7ppm ~
The peak around 4.1 ppm is that of a methylene proton derived from ester-bonded cyclohexanedimethanol, the peak around 4.6 ppm is that of a methylene proton at the allyl position, and the peak around 5.3 ppm is the allyl position. Of the terminal proton of the double bond of
The peak around 5.8 ppm is due to the proton inside the allyl double bond.

In FIG. 2, the peak at 1738 cm ^-1 is the absorption of the carbonyl stretching vibration of the carboxyl group. Gas chromatography (manufactured by Shimadzu Corporation, GC-14B,
Column used for hydrogen flame ionization detector OV-17 0.5
m, the sample A contained 3.88% by mass of diallyl glutarate.

(Production Example 2) 660.6 g of succinic anhydride, 1056 g of allyl alcohol, 1000 ml of benzene, 6.61 g of concentrated sulfuric acid (1% by mass based on succinic anhydride) were placed in a 3 liter three-necked flask equipped with a distillation apparatus. ) And heated at 100 ° C. under a stream of nitrogen to produce H
₂ O was distilled off. The reaction is continued until the distilled of H ₂ O of theory, where the 109 g (100% relative to the theoretical H ₂ O evaporated amount), the reactor was cooled. The obtained reaction solution is
Neutralized with OH aqueous solution and washed with water. After distilling off benzene and excess allyl alcohol, the residue was purified by distillation under reduced pressure to obtain 1130 g of diallyl succinate as a colorless and transparent liquid.

In a 3 liter three-necked flask equipped with a distillation apparatus, 1784 g of diallyl succinate, 829 g of 1,4-cyclohexanedimethanol, and dibutyltin oxide.
784 g (1% by mass based on diallyl succinate) was charged and heated at 180 ° C. under a nitrogen stream to distill off allyl alcohol produced. 418 g of allyl alcohol
After the distillation was completed, the pressure in the reaction system was reduced to 1.33 kPa, and the distillation speed of allyl alcohol was increased. After distilling off the theoretical amount (618 g) of allyl alcohol, the mixture was further heated for 1 hour, kept at 190 ° C.-0.13 kPa for 1 hour, cooled, and cooled with an allyl ester compound (hereinafter “Sample B”). 1897 g).
The 400 MHz ¹ H-NMR spectrum (solvent: CDCl ₃ ) and the FT-IR spectrum of the obtained sample B are shown in FIGS. 3 and 4, respectively.

In FIG. 3, peaks around 0.9 ppm to 2.0 ppm are those of protons derived from the cyclohexane ring, peaks around 2.6 ppm to 2.7 ppm are those of protons derived from the succinic acid skeleton, 3.9 ppm ~
The peak around 4.2 ppm is that of a methylene proton derived from ester-bonded cyclohexane dimethanol, the peak around 4.5 ppm is that of a methylene proton in the allyl position, and the peak around 5.3 ppm is the allyl position. Of the terminal proton of the double bond of
The peak around 5.9 ppm is due to the proton inside the allylic double bond.

In FIG. 4, the peak at 1736 cm ^-1 is the absorption of the carbonyl stretching vibration of the carboxyl group. Gas chromatography (manufactured by Shimadzu Corporation, GC-14B,
Column used for hydrogen flame ionization detector OV-17 0.5
m, the sample B contained 11.8% by mass of diallyl succinate.

(Production Example-3) Dimethyl 2-methylsuccinate 100 was placed in a 1-liter three- necked flask equipped with a distillation apparatus.
0 g, allyl alcohol 1441 g, potassium acetate 25
g, 5 g of calcium hydroxide and 11
The resulting methanol was distilled off by heating at 0 ° C. The reaction is continued until the theoretical amount of methanol is distilled off.
When 7 g (97%) had been distilled off, the reactor was cooled. The obtained reaction solution was Suction filtration was performed using a 5C Kiriyama funnel to separate a solid substance in the reaction solution. Thereafter, distillation purification was performed under reduced pressure to obtain 1200 g of diallyl 2-methylsuccinate which was a colorless and transparent liquid.

In a 1-liter three-necked flask equipped with a distillation apparatus, 640 g of diallyl 2-methylsuccinate, 336 g of 1,4-cyclohexanedimethanol, and 0.639 g of dibutyltin oxide were charged, and heated at 180 ° C. under a nitrogen stream to produce. The coming allyl alcohol was distilled off. When about 190 g of allyl alcohol was distilled off, the pressure in the reaction system was reduced to 1.33 kPa, and the distillation rate of allyl alcohol was increased. After distilling off the theoretical amount (270.7 g) of allyl alcohol, the mixture was further heated for 1 hour at 190 ° C.
After maintaining at -0.13 kPa for 1 hour, the reactor was cooled to obtain 705 g of an allyl ester compound (hereinafter, referred to as "sample C"). 400M of sample C obtained
The ¹ H-NMR spectrum (solvent: CDCl ₃ ) and the FT-IR spectrum at Hz are shown in FIGS. 5 and 6, respectively.

In FIG. 5, peaks near 0.9 ppm to 2.0 ppm are those of protons derived from the cyclohexane ring, and among them, peaks near 1.2 ppm are peaks derived from the branched methyl group of succinic acid. Yes, 2.4pp
The peak around m to 3.0 ppm is that of a proton derived from the 2-methylsuccinic acid skeleton, and is from 3.9 ppm to 4.2.
The peak around ppm is that of a proton of methylene derived from cyclohexanedimethanol with an ester bond,
The peak around 4.6 ppm is that of the methylene proton at the allylic position, and the peak around 5.3 ppm is that of the proton at the terminal of the double bond at the allylic position.
The peak around pm to 6.0 ppm is due to the proton inside the allyl double bond.

In FIG. 6, the peak at 1738 cm ^-1 is the absorption of the carbonyl stretching vibration of the carboxyl group. Gas chromatography (manufactured by Shimadzu Corporation, GC-14B,
Column used for hydrogen flame ionization detector OV-17 0.5
m, when analyzed under the temperature condition of 160 ° C.), the sample C contained 3.8% by mass of diallyl 2-methylsuccinate.

(Production Example-4) 660.6 g of succinic anhydride, 1056 g of allyl alcohol, 1000 ml of benzene, 6.61 g of concentrated sulfuric acid (1% by mass based on succinic anhydride) were placed in a 3 liter three-necked flask equipped with a distillation apparatus. ) And heated at 100 ° C. under a stream of nitrogen to produce H
₂ O was distilled off. The reaction was continued until the theoretical amount of H ₂ O was distilled off, and 109 g (100% of the theoretical H ₂ O distilling amount) of H ₂ O was removed.
When O was distilled off, the reactor was cooled. The obtained reaction solution was neutralized with an aqueous NaOH solution and washed with water. After distilling off benzene and excess allyl alcohol, distillation and purification were carried out under reduced pressure.
130 g were obtained.

In a 1-liter three-necked flask equipped with a distillation apparatus, 396.4 g of diallyl succinate, 2,2-bis [4
-(2-hydroxyethoxy) cyclohexyl] propane (trade name: HBA-2 manufactured by Nippon Emulsifier Co., Ltd.) 32
8.5 g and 0.4 g of dibutyltin oxide were charged and heated at 180 ° C. in a nitrogen stream to distill off allyl alcohol produced. When about 81.3 g of allyl alcohol was distilled off, the pressure in the reaction system was reduced to 1.33 kPa, and the distillation rate of allyl alcohol was increased. After distilling off the theoretical amount (116.2 g) of allyl alcohol, the mixture was further heated for 1 hour, kept at 190 ° C.-0.13 kPa for 1 hour, cooled, and cooled with an allyl ester compound (hereinafter, referred to as “ 256 g of sample D "). The 400 MHz ¹ H-NMR spectrum (solvent: CDCl ₃ ) and the FT-IR spectrum of the obtained sample D are shown in FIGS. 7 and 8, respectively.

In FIG. 7, the peak around 0.6 ppm to 0.8 ppm is that of a proton derived from the propane skeleton.
The peak around 0.9 ppm to 2.2 ppm is for a proton derived from a cyclohexane ring, the peak around 2.6 ppm is for a proton derived from a succinic acid skeleton,
The peak near 3.6 ppm is that of a methylene proton derived from cyclohexanedimethanol that is ester-bonded, the peak near 4.6 ppm is that of a methylene proton in the allyl position, and the peak near 5.3 ppm is the allyl position. Of the terminal proton of the double bond of
The peak around 5.8 ppm to 6.0 ppm is for a proton on the internal side of the double bond at the allylic position.

In FIG. 8, the peak at 1737 cm ^-1 is the absorption of the carbonyl stretching vibration of the carboxyl group. Gas chromatography (manufactured by Shimadzu Corporation, GC-14B,
Column used for hydrogen flame ionization detector OV-17 0.5
m, the sample was analyzed under the temperature condition of 160 ° C.). As a result, Sample D contained 12.3% by mass of diallyl succinate.

In the following Examples, in order to reduce the viscosity of Samples A to D, dilution was carried out using a compound of the following structural formula (19) or (24).

Structural formula (19)

Embedded image

Structural formula (24)

Embedded image Table 1 shows the types and compositions of the diluted compounds.

Example 1 (Production of Composition for Plastic Lens) As shown in Table 1, 40.0 parts by mass of the allyl ester compound of Sample A and 60.50 parts of the compound of structural formula (24) were used.
0 parts by mass and 3 parts by mass of diisopropyl peroxydicarbonate (IPP) were blended, mixed and stirred to obtain a completely uniform solution composition, and the viscosity at that time was measured. Thereafter, the container containing the solution was placed in a desiccator that can be depressurized, and the pressure in the solution was reduced by a vacuum pump for about 15 minutes, thereby degassing the gas in the solution. This solution composition is carefully injected with a syringe so as not to mix gas into a mold made of a glass mold for an eyeglass plastic lens and a mold made of a resin gasket, and then placed in an oven at 40 ° C. for 7 hours. 10 hours from 40 ° C to 60 ° C, 6
3 hours from 0 ° C to 80 ° C, 1 hour at 80 ° C, 2 hours at 85 ° C
Curing was carried out by heating for a programmed period of time. Table 1 shows the measurement results of the refractive index, Abbe number, and Barcol hardness of the obtained lens, and the results of the curing shrinkage.

[0150]

[Table 1]

Examples 2 to 5 and Comparative Examples 1 to Comparative Examples
2 (Production of composition for plastic lens) A composition was prepared according to the formulation shown in Table 1, and the viscosity was measured in the same manner as in Example 1. Thereafter, the composition was cured, and the refractive index and Abbe number of the lens were obtained. , Barcol hardness and cure shrinkage. Table 1 shows the results.

Examples 6 to 10 and Comparative Examples 3 to
Example 4 (Production of plastic lens) Further , the composition described in Table 1 (Examples 1 to 5,
The container in which the solution of Comparative Example 1 or Comparative Example 2 was placed was placed in a desiccator capable of reducing the pressure, and the pressure in the solution was reduced by a vacuum pump for about 15 minutes to degas the gas in the solution. This solution composition is carefully injected into a mold (thickness: 3 mm) assembled with a glass mold and a resin gasket with a syringe so that no gas is mixed therein, and then in an oven at 40 ° C. for 3 hours. Curing was carried out by heating at 40 ° C. to 85 ° C. for 3 hours and at 85 ° C. for 2 hours. Whether or not the cured product was cracked when cured by the above method was visually observed. Table 2 shows the results.

[0153]

[Table 2]

Example 11 (Production of plastic lens) As shown in Table 3, 95.0 parts by mass of diethylene glycol bis (allyl carbonate) (trade name: CR-39 (registered trademark) manufactured by PPG) and 5 parts of sample A were prepared. 0.0 parts by mass, diisopropyl peroxydicarbonate (IP
3 parts by mass of P) was blended, mixed and stirred to obtain a completely uniform solution composition, and the viscosity at that time was measured. Thereafter, the container containing the solution was placed in a desiccator that can be depressurized, and the pressure in the solution was reduced by a vacuum pump for about 15 minutes, thereby degassing the gas in the solution. This solution composition was carefully injected with a syringe so that no gas was mixed into a glass mold for spectacle plastic lenses and a mold assembled with a resin gasket, and then heated in an oven at 40 ° C.
7 hours, 40 ° C to 60 ° C for 10 hours, 60 ° C to 80 ° C
Curing was performed by heating at a programmed temperature of 3 hours to 80 ° C, 1 hour at 80 ° C, and 2 hours at 85 ° C.

Table 3 shows the measurement results of the refractive index, Abbe number, and Barcol hardness of the obtained lenses, and the evaluation results of uneven dyeing. The viscosity (25 ° C.) of the compound before curing in Example 11 was less than 100 mPa · s.

Examples 12 to 15 and Comparative Example 5
Production of a plastic lens) A composition was prepared according to the formulation shown in Table 3, and the viscosity was measured in the same manner as in Example 6. Thereafter, the composition was cured, and the refractive index, Abbe number, and Barcol hardness of the lens were measured. And uneven dyeing were evaluated. Table 3 shows the results.

The viscosities (25 ° C.) of the compounds before curing in Examples 12 to 15 were all less than 100 mPa · s.

[0158]

[Table 3]

From the results in Tables 1 and 2, according to the present invention,
It is clear that a plastic lens having a high Abbe number and a small cure shrinkage can be produced, and that curing can be performed in a short time.

From the results shown in Table 3, it was found that the plastic lens material of the present invention also has an effect of improving the dyeing of polyethylene glycol bis (allyl carbonate) resin.

[0161]

As described above, the compounds of the present invention are:
Compared to conventional polyethylene glycol bis (allyl carbonate) resin, it is a compound that has a small curing shrinkage ratio. Furthermore, it is possible to produce a cured product having a high Abbe number similarly to polyethylene glycol bis (allyl carbonate) resin. It is clear. Therefore, it is possible to produce a plastic lens more efficiently than the conventional polyethylene glycol bis (allyl carbonate) resin.

Further, by using the compound of the present invention in combination with a polyethylene glycol bis (allyl carbonate) resin, it is possible to improve the dyeing unevenness which occurs when the polyethylene glycol bis (allyl carbonate) resin is dyed. .

[0163]

[Brief description of the drawings]

The figures shown below are a 400 MHz ¹ H-NMR spectrum chart and an FT-IR spectrum chart of the compounds for plastic lens materials described in Examples.

[0164]

FIG. 1 is a 400 MHz ¹ H-NMR spectrum chart of an allyl ester compound produced in Production Example-1.

FIG. 2 is an FT-IR spectrum chart of the allyl ester compound produced in Production Example-1.

FIG. 3 is a 400 MHz ¹ H-NMR spectrum chart of the allyl ester compound produced in Production Example-2.

FIG. 4 is an FT-IR spectrum chart of the allyl ester compound produced in Production Example-2.

FIG. 5 is a 400 MHz ¹ H-NMR spectrum chart of the allyl ester compound produced in Production Example-3.

[0165]

FIG. 6 is an FT-IR spectrum chart of the allyl ester compound produced in Production Example-3.

FIG. 7 is a 400 MHz ¹ H-NMR spectrum chart of the allyl ester compound produced in Production Example-4.

FIG. 8 is an FT-IR spectrum chart of the allyl ester compound produced in Production Example-4.

Continued on the front page (51) Int.Cl. ⁷ Identification FI FI Theme Court II (Reference) B29L 11:00 B29L 11:00 (72) Inventor Kazufumi Kai Oita City, Oita City, Oita Prefecture 2 Nakanoshima 2 Showa Denko Co., Ltd. Within the Production and Technology Management Department (72) Inventor Tsuneo Tajima Oita Prefecture Oita City, Nakanoshima 2 Showa Denko Co., Ltd.Oita Production and Technology Management Department (72) Inventor Hiroshi Uchida Oita Prefecture Oita City, Nakanoshima 2 Showa Denko Stock F-term (reference) in the Oita Production & Technology Division 4F204 AA20A AH74 EA03 EA04 EB01 EE02 EF01 EF27 EK13 EK17 4J100 AG15P AG69P AG69Q AG70Q AG71Q BA02Q BA15P BA22Q BC04P BC04Q BC08Q BC27Q CA04 DA09 FA22 FA03

Claims (11)

[Claims] 1. A plastic lens material having at least one of the groups represented by the following general formula (1) as a terminal group and having a group represented by the following general formula (2) as a repeating unit. General formula (1) (In the formula, R ¹ each independently represents either an allyl group or a methallyl group, and A ¹ each independently represents an organic residue derived from a divalent carboxylic acid or carboxylic anhydride.) (2) (Wherein A ² independently represents an organic residue derived from a divalent carboxylic acid or carboxylic acid anhydride;
Each independently represents an organic residue derived from a polyhydric alcohol having 2 to 3 hydroxyl groups and having an alicyclic structure in the molecule. However, X is an ester bond, and the above-mentioned general formula (1) is a terminal group, and the above-mentioned general formula (2)
Is a repeating unit. ) 2. The polyhydric alcohol is represented by the following structural formula (1)
The plastic lens material according to claim 1, wherein the plastic lens material is at least one selected from compounds represented by the following structural formulas (7) and (3). Structural formula (1) Structural formula (2) Structural formula (3) Structural formula (4) Structural formula (5) Structural formula (6) Structural formula (7) General formula (3) (Wherein, R ² independently represents at least one or more selected from organic groups represented by the following structural formulas (8) to (10), and R ³ each independently represent the following structural formula: (11) to at least one selected from the following structural formulas (13), wherein a and b are each independently 0
Alternatively, Y represents an integer of 1 to 10, and Y is the following structural formula (1
4) or any organic group selected from the following structural formula (15). ) Structural formula (8) Structural formula (9) Structural formula (10) Structural formula (11) Structural formula (12) Structural formula (13) Structural formula (14) Structural formula (15) 3. A plastic lens material by subjecting at least one selected from the following formula (4) to a transesterification reaction with the polyhydric alcohol according to claim 1 in the presence of a catalyst. The method for producing a material according to claim 1, further comprising: General formula (4) (In the formula, A represents an organic residue derived from a divalent carboxylic acid or a carboxylic anhydride, and R ⁴ and R ⁵ each independently represent either an allyl group or a methallyl group.) 4. The catalyst used in the process according to claim 3,
Tetraisopropoxy titanium, tetrabutoxy titanium,
The method for producing a plastic lens material according to claim 3, wherein the material is at least one selected from the group consisting of dibutyltin oxide, dioctyltin oxide, hafnium acetylacetone, and zirconium acetylacetone. 5. A composition for a plastic lens, comprising at least one of the plastic lens materials according to claim 1 or 2. 6. A plastic lens comprising 0.1 part by mass to 10 parts by mass of at least one radical polymerization initiator based on 100 parts by mass of the plastic lens composition according to claim 5. Composition. 7. The plastic lens composition according to claim 6, wherein at least one or more radical polymerization initiators contain diisopropyl peroxydicarbonate. 8. The composition for a plastic lens according to claim 5, wherein the composition comprises 25 parts of the composition.
A composition for a plastic lens, which has a viscosity at 1000C of not more than 1000 mPas. 9. A plastic lens obtained by curing the plastic lens composition according to any one of claims 5 to 8. 10. The plastic lens according to claim 9, wherein the curing shrinkage at 23 ° C. is 10.0% or less. 11. The plastic lens according to claim 9, wherein said plastic lens is produced by a casting method at a polymerization temperature of 30 ° C. to 120 ° C. and a polymerization time of 0.5 to 100 hours. A method for producing a plastic lens.