WO1999032907A1 - Synthetic resin lens and process for producing the same - Google Patents

Abstract

A synthetic resin lens which has a high refractive index, a low specific gravity, and excellent transparency, is reduced in the dispersion of light, and is easily molded through cast polymerization without causing the sealing material to dissolve away or be damaged. The synthetic resin lens is characterized by being obtained by polymerizing a monomer mixture comprising [A] a polyfunctional (meth)acrylate having a urethane bond, [B] divinylbenzene, and [C] a polythiol compound using a radical polymerization initiator.

Description

 Description Synthetic resin lens and method of manufacturing the same Technical field

 The present invention relates to a synthetic resin lens and a method for producing the same, and more particularly, to a lens for spectacles having a high refractive index (for example, 1.57 or more) and low light dispersion (for example, an Abbe number of 30 or more). The present invention relates to a synthetic resin lens having excellent characteristics, and a method for producing such a synthetic resin lens. Background technology

 Recently, synthetic resin lenses have been widely used as eyeglass lenses. Important characteristics required of such a synthetic resin lens include (1) a high refractive index and (2) low light dispersion.

 According to the synthetic resin having a high refractive index, the thickness of the peripheral portion of the lens for correcting myopia and the thickness of the central portion of the lens for correcting hyperopia and the lens for presbyopia can be reduced, thereby reducing the weight of the lens. And ^ can be improved.

 Further, according to the synthetic resin having low light dispersibility, a lens with small chromatic aberration can be obtained.

 On the other hand, polydiethylene dalichol bisaryl carbonate (CR-39), which is widely used as a constituent material for spectacle lenses, has a low refractive index of about 1.50, so that the thickness of the lens can be sufficiently increased. The size cannot be reduced, and the appearance is not favorable.

 Under such circumstances, development of a synthetic resin lens having a high refractive index and a low dispersibility has been desired.

As a means for responding to such a request, attempts have been made to introduce a sulfur atom into a synthetic resin (Japanese Patent Application Laid-Open Nos. 2-28059 / 1990 and 5-2005050 / 1990). See). In this case, it is obtained with an increase in the content of sulfur atoms. The refractive index of the lens increases and the light dispersion decreases.

 The following methods (1) to (3) are known as methods for introducing a sulfur atom into a synthetic resin.

 (1) A method of synthesizing a radically polymerizable monomer containing a sulfur atom and polymerizing the monomer (see JP-A-63-188660 and JP-A-2-261808).

(2) A method of reacting a mercaptan compound with an isocyanate compound to obtain a thiourethane polymer (see JP-A-60-199016 and JP-A-3-236386).

 (3) A method of adding a mercaptan compound to a double bond portion of a radical polymerizable monomer (see JP-A-62-270627, JP-A-63-235332, and JP-A-11-197528).

 However, in the above method (1), the operation of synthesizing and purifying a monomer containing a sulfur atom is complicated. For example, the monomer is reacted by reacting a (meth) atalylic acid derivative with a mercaptan compound to convert the monomer. When it is obtained, the mercaptan compound is added to the double bond of the (meth) acrylic acid derivative, and the yield of the target monomer is significantly reduced.

 In the above method (2), when molding a lens by the casting polymerization method, a single amount of a seal material (for example, a gasket / tape for sealing a joint between a male mold and a female mold) is used. There is a problem of elution into the body composition, and the design for preventing this is complicated.

 In addition, the method (2) also has a problem in that the glass constituting the mold and the isocyanate compound react with each other, so that the releasability is impaired. In this case, it is conceivable to add a release agent to the monomer composition. However, the release agent may remain in the polymer (lens material) and adversely affect the processability of the lens material. is there. Also in the above method (3), there is a problem that when the lens is molded by the casting polymerization method, the sealing material of the mold elutes into the monomer composition.

Here, in order to prevent elution and breakage of the sealing material, it is also possible to control the viscosity of the system by performing a prepolymerization treatment of the monomer composition (Japanese Patent Laid-Open No. 63-309). No. 509, Japanese Patent Application Laid-Open No. 2-289962, Japanese Patent Application Laid-Open No. 2-283331)

 However, it is difficult to control the viscosity within a suitable range by the prepolymerization treatment, and a reproducible prepolymer (monomer composition) cannot be obtained. Furthermore, when performing thermal polymerization or photopolymerization as this prepolymerization treatment, the stability of the prepolymer (monomer composition) is impaired by the residual polymerization initiator. Disclosure of the invention

 [Problems to be solved by the invention]

 The present invention has been made based on the above circumstances.

 A first object of the present invention is to provide a synthetic resin lens having a high refractive index and low light dispersibility, and a method for producing the same.

 A second object of the present invention is to provide a synthetic resin lens having low specific gravity and excellent transparency, and a method for producing the same.

 A third object of the present invention is to provide a synthetic resin lens and a method for producing the same, which can be easily molded without dissolving or breaking a sealing material when molded by a casting polymerization method. Is to do.

 [Means for solving the problem]

 The synthetic resin lens of the present invention comprises a radical polymerization initiator comprising a monomer mixture containing [A] a polyfunctional (meth) acrylate having a urethane bond, [B] dibutylbenzene, and [C] a polythiol compound. Characterized by being obtained by polymerization using

Further, [A] a polyfunctional (meth) acrylate having a urethane bond includes a (meth) acrylate (a ¹ ) having a hydroxyl group in a molecule and a polyisocyanate (a) having two or more isocyanate groups in a molecule. a ² ) is preferably obtained by reacting

Further, [A] a polyfunctional (meth) acrylate having a urethane bond has a hydroxyl group-containing (meth) acrylate (a ') and a molecule having an isocyanate group. A polyisocyanate having two or more (a ² ), [OH] a mole number of a hydroxyl group of the (meth) acrylate (a ¹ ), and a polyisocyanate (a ² ) of the polyisocyanate (a ² ). When the number of moles is [NCO], it is preferably obtained by reacting at a ratio of [OH] / [NCO] of 1 or more, especially 1 to 1.3.

Furthermore, [A] a polyfunctional having a urethane bond (meth) Atari rate, having a hydroxyl group in the molecule (meth) and Atari rate ^(a]), polyisobutylene Xia sulfonates having two or more Isoshianeto groups in the molecule ( a ² ) is preferably obtained in the presence of a highly active organotin-based catalyst.

Further, [A] a polyfunctional (meth) acrylate having a urethane bond includes a (meth) acrylate (a ¹ ) having a hydroxyl group in a molecule and a polyisocyanate (a) having two or more isocyanate groups in a molecule. It is preferably obtained by reacting a ² ) with a compound (a ³ ) having two or more hydroxyl groups in the molecule.

Further, [A] a polyfunctional (meth) acrylate having a urethane bond includes a (meth) acrylate (a ¹ ) having a hydroxyl group in a molecule and a polyisocyanate (a) having two or more isocyanate groups in a molecule. a ² ) and a compound (a ³ ) having two or more hydroxyl groups in the molecule, the number of moles of the hydroxyl groups of the (meth) acrylate (a ¹ ) and the compound (a ³ ) is represented by [OH When the number of moles of isocyanate groups in the polyisocyanate (a ² ) is [NCO], the reaction is carried out at a ratio of [OH] / [NCO] of 1 or more, especially 1 to 1.3. It is preferably obtained by the following method.

Also, [A] a polyfunctional (meth) acrylate having a urethane bond includes a (meth) acrylate (a ¹ ) having a hydroxyl group in the molecule and a polyisocyanate (a) having two or more isocyanate groups in the molecule. It is preferably obtained by reacting ² ) with a compound (a ³ ) having two or more hydroxyl groups in the molecule in the presence of a highly active organotin catalyst.

The synthetic resin lens of the present invention comprises [A] a polyfunctional (meth) acrylate having a urethane bond, [B] dibutylbenzene, [C] a polythiol compound, and [D] It is obtained by polymerizing a monomer mixture containing an aromatic compound having two or more (meth) acrylic groups using a radical polymerization initiator.

 The synthetic resin lens of the present invention comprises [A] a polyfunctional (meth) acrylate having a urethane bond, [B] dibutylbenzene, [C] a polythiol compound, and [D] two or more (meth) acrylinyl groups. A monomer mixture containing the aromatic compound having a mass ratio of 10 to 70: 10 to 60: 5 to 50: 0 to 30 by using a radical polymerization initiator. And obtained by polymerization.

 The synthetic resin lens of the present invention comprises [A] a polyfunctional (meth) acrylate having a urethane bond, [B] dibutylbenzene, [C] a polythiol compound, and [D] two or more (meth) acryl groups. A monomer mixture containing the aromatic compound having a ratio satisfying the following formula (i) by using a radical polymerization initiator to polymerize the monomer mixture.

 Formula (i) 1.5 (a + b + d) Zc 3.0

 Here, a: [A] the number of moles of the (meth) acryl group of the polyfunctional (meth) acrylate having a urethane bond

 b: [B] mole number of a Bier group possessed by dibierbenzene c: [C] mole number of a thiol group possessed by a polythiol compound d-CD) (meth) possessed by an aromatic compound possessing two or more acrylic groups ) Number of moles of acrylic group

 The method for producing a synthetic resin lens of the present invention comprises the steps of: preparing a monomer mixture containing [A] a polyfunctional (meth) atalylate having a urethane bond, [B] divininolebenzene, and [C] a polythiol compound, It is characterized in that polymerization is carried out using a polymerization initiator.

[A] The urethane bond can be obtained by reacting (meth) acrylate (a ¹ ) having a hydroxyl group in the molecule with polyisocyanate (a ² ) having two or more isocyanate groups in the molecule. A polyfunctional (meth) acrylate having a polyfunctional (meth) acrylate having a urethane bond is prepared. Preferably, the monomer mixture is polymerized.

Further, a (meth) acrylate (a ′) having a hydroxyl group in the molecule and a polyisocyanate (a ² ) having two or more isocyanate groups in the molecule can be obtained by mixing the (meth) acrylate (a ¹ ) ) Is [〇H], and the number of moles of isocyanate groups in the polyisocyanate (a ² ) is [NCO], the value of [OH] / [NCO] is 1 or more, In particular, [A] a polyfunctional (meth) acrylate having a urethane bond is prepared by reacting at a ratio of 1 to 1.3, and the obtained [A] polyfunctional (meth) acrylate having a urethane bond is obtained. It is preferable to polymerize a monomer mixture containing

In addition, a (meth) atalylate (a ¹ ) having a hydroxyl group in a molecule and a polyisocyanate (a ² ) having two or more isocyanate groups in a molecule are combined in the presence of a highly active organotin catalyst. [A] A polyfunctional (meth) acrylate having a urethane bond is prepared by reacting the obtained monomer mixture with the obtained monomer mixture containing the [A] polyfunctional (meth) acrylate which has a urethane bond. Polymerization is preferred. Also, (meth) acrylate (a ¹ ) having a hydroxyl group in the molecule, polyisocyanate (a ² ) having two or more isocyanate groups in the molecule, and two or more hydroxyl groups in the molecule [A] a polyfunctional (meth) acrylate having a urethane bond is prepared by reacting the compound (a ³ ) with the compound (a ³ ), and the resulting polyfunctional (meth) acrylate having a [A] urethane bond is contained. It is preferable to polymerize the resulting monomer mixture.

Also, (meth) acrylate (a ¹ ) having a hydroxyl group in the molecule, polyisocyanate (a ² ) having two or more isocyanate groups in the molecule, and two or more hydroxyl groups in the molecule The compound (a ³ ) having the (meth) acrylate (a ¹ ) and the compound (a ³ ) having a hydroxyl number of [OH], the polyisocyanate (a ² ) having an isocyanate group When the number of moles is [NCO], the reaction is performed at a ratio of [OH] / [NCO] of 1 or more, particularly 1 to 1.3, so that [A] a polyfunctional (meth) atali having a urethane bond is obtained. And (A) a simple composition containing the obtained polyfunctional (meth) acrylate having a urethane bond. It is preferred to polymerize the monomer mixture.

Also, (meth) acrylate (a ¹ ) having a hydroxyl group in the molecule, polyisocyanate (a ² ) having two or more isocyanate groups in the molecule, and two or more hydroxyl groups in the molecule [A] Polyfunctional (meth) atalylate having a urethane bond was prepared by reacting the compound (a ³ ) with the compound (a ³ ) in the presence of a highly active organotin catalyst, and the obtained [A] urethane bond It is preferable to polymerize a monomer mixture containing a polyfunctional (meth) acrylate which has

Further, a (meth) acrylate having a hydroxyl group in the molecule (a ¹ ) and a polyisocyanate having two or more isocyanate groups in the molecule (a ² ) are subjected to a urethanation reaction in [B] divinyl benzene. Thus, a mixed system of [A] a polyfunctional (meth) acrylate having a urethane bond and [B] dibutylbenzene is prepared, and [C] a polythiol compound is added to the mixed system and mixed. It is preferable to prepare a monomer mixture and polymerize this monomer mixture using a radical polymerization initiator.

Also, (meth) acrylate (a ¹ ) having a hydroxyl group in the molecule, polyisocyanate (a ² ) having two or more isocyanate groups in the molecule, and two or more hydroxyl groups in the molecule Urethanation reaction of the compound (a ³ ) with the compound (a ³ ) in [B] dibutylbenzene to form a mixed system of [A] a polyfunctional (meth) acrylate having a urethane bond and [B] dibibenzenebenzene. It is preferable to prepare a monomer mixture by adding and mixing the (C) polythiol compound into the mixed system, and then polymerize the monomer mixture using a radical polymerization initiator. .

 The method for producing a synthetic resin lens of the present invention comprises: [A] a polyfunctional (meth) acrylate having a urethane bond, [B] dibutylbenzene, [C] a polythiol compound, and [D] (meth) acrylic group. A monomer mixture containing two or more aromatic compounds is polymerized using a radical polymerization initiator.

The method for producing a synthetic resin lens of the present invention comprises: [A] a polyfunctional (meth) acrylate having a urethane bond, [B] dibutylbenzene, [C] a polythiol compound, and [D] an (meth) acryl group. Aromatic compounds having two or more by mass ratio of 10 to It is characterized in that a monomer mixture containing 70: 10 to 60: 5 to 50: 0 to 30 is polymerized by using a radical polymerization initiator.

 The method for producing a synthetic resin lens of the present invention comprises: [A] a polyfunctional (meth) acrylate having a urethane bond, [B] dibutylbenzene, [C] a polythiol compound, and [D] a (meth) acryl group. It is characterized in that a monomer mixture containing at least one aromatic compound having a ratio satisfying the following formula (i) is polymerized using a radical polymerization initiator.

 Formula (i) 1.5 (a + b + d) Zc 3, 0

 Here, a: [A] the number of monoles of the (meth) acrylic group of the polyfunctional (meth) acrylate having a urethane bond

 b: [B] mole number of vinyl group of dibutylbenzene c: [C] mole number of thiol group of polythiol compound d: [D] of aromatic compound having two or more (meth) acrylic groups ( Meth) Number of moles of acrylic group

In addition, (B) urethanation reaction in (B) divinyl benzene is carried out with (meth) acrylate (a ′) having a hydroxyl group in the molecule and polyisocyanate (a ² ) having two or more isocyanate groups in the molecule. Thus, a mixed system of [A] a polyfunctional (meth) atalylate having a urethane bond and [B] dibutylbenzene is prepared, and [C] a polythiol compound and [D] (meta) are added to the mixed system. It is preferable to prepare a monomer mixture by adding and mixing with an aromatic compound having two or more acrylic groups, and polymerize this monomer mixture using a radical polymerization initiator.

Also, (meth) acrylate (a ′) having a hydroxyl group in the molecule, polyisocyanate (a ² ) having two or more isocyanate groups in the molecule, and two or more hydroxyl groups in the molecule The compound (a ³ ) has a urethanation reaction in [B] dibutylbenzene to form a mixed system of [A] a polyfunctional (meth) acrylate having a urethane bond and [B] divinylbenzene. The mixture is prepared as follows: [C] a polythiol compound and [D] an aromatic compound having two or more (meth) acryl groups. It is preferable that a monomer mixture is prepared by adding and mixing the monomer mixture, and the monomer mixture is polymerized using a radical polymerization initiator.

 Figure 3

 (1) [A3 Since a polyfunctional (meth) acrylate which has a urethane bond is contained in the monomer mixture, the copolymer (lens material) obtained by polymerizing the monomer mixture has a crosslinked structure. be introduced. In addition, the copolymer having a urethane bond has a small thermal deformation in a low temperature range.

 (2) The urethane bond introduced into the copolymer imparts toughness to the copolymer, makes the synthetic resin lens finally obtained hard to crack, and further improves the dyeability of the synthetic resin lens and the hard coat. Adhesion can also be improved.

 (3) [A] The viscosity of a monomer mixture containing a polyfunctional (meth) acrylate which has a urethane bond is relatively high at 35 to 200 cp (25 ° C). During the casting polymerization of the monomer mixture, the sealing material can be easily formed (molded) without elution or breakage of the sealing material.

 (4) [A] The viscosity of the monomer mixture is adjusted to a suitable range by containing a polyfunctional (meth) acrylate which has a urethane bond, and the monomer mixture has good storage stability. It has the property.

 (5) [A] Polyfunctional (meth) atalylate having a urethane bond and [B] divinylbenzene undergo a copolymerization reaction, and the unsaturated double bond of both components is

[C] A polythiol compound is added (addition reaction of a thiol group to an unsaturated double bond proceeds simultaneously). The copolymer (lens material) into which the sulfur atom is introduced in this way has both high refractive index and low dispersibility.

 [Embodiment of the invention]

 Hereinafter, the present invention will be described specifically.

 In the present invention, “(meta) acrylate” means “acrylate” and

"(Meth) acrylic group" means both "acrylic group" and "methacrylic group".

The monomer mixture used to obtain the synthetic resin lens of the present invention is ( _A ) urethane A polyfunctional (meth) acrylate having a tan bond, [B] divinylbenzene,

[C] It may contain a polythiol compound as an essential component, and [D] may contain an aromatic compound having two or more (meth) acryl groups.

 The [A] polyfunctional (meth) acrylate having a urethane bond (hereinafter, also referred to as “[A] component”) constituting the monomer mixture is as follows:

(1) by subjecting a (meth) acrylate (a ′) having a hydroxyl group in the molecule to a polyisocyanate (a ² ) having two or more isocyanate groups in the molecule to undergo a urethanization reaction, or

(2) (meth) acrylate (a ') having a hydroxyl group in the molecule, polyisocyanate (a ² ) having two or more isocyanate groups in the molecule, and a compound having two or more hydroxyl groups in the molecule (a ³ ) and urethanation reaction

Can be prepared.

Here, (meth) acrylate (a ¹ ) having a hydroxyl group in the molecule [hereinafter, simply referred to as “(meth) acrylate (a ¹ )”. ] 2-hydroxyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutynole (meth) acrylate, 2-hydroxy-1,3-dimethacryloxypropane, 2-methacrylic Loxyshetyl 2-hydroxypropyl phthalate, 2-hydroxy 3-acryloxypropyl methacrylate, 3-chloro-2-hydroxypropyl methacrylate, 2-hydroxy 3-phenoxypropyl phthalate, etc. These can be used alone or in combination of two or more.

Polyisocyanate (a ² ) having two or more isocyanate groups in the molecule [hereinafter, simply referred to as “polyisocyanate (a ² )”. ] Hexamethylene diisocyanate, octamethylene diisocyanate, isophorone diisocyanate, 2,2,4-trimethinolehexamethylene diisocyanate, dicyclohexynolemethane-1,4,4-diisocyanate, Tetramethylene diisocyanate, 1,3-bis (isocyanatomethyl) cyclohexane, tolylene diisocyanate, 4,4-diphenyl methane diisocyanate, naphthalene diisocyanate , 3,3-Dimethyl-4,4-bisphenylenediisocyanate, m-xylylenediisocyanate, hexamethylenediisocyanate buretation reaction product, isocyanate compound with trimer structure or trimethylolpropane Reaction product with adduct, trifunctional or tetrafunctional polyisocyanate compound derived from isophorone diisocyanate, 2-isocyanateethyl-2,6 diisocyanateethylhexanoate And the like, and these can be used alone or in combination of two or more.

Further, a compound having two or more hydroxyl groups in the molecule used in the reaction (2) (a ³ ) [hereinafter referred to as “hydroxyl-containing compound (a ³ )”. ], 2,2'-thiojetanol, ethylenebis (2-hydroxyshetyl sulfide), 4,4'-thio (6-tert-butyl-meth-cresol), 4,4-thiodiphenol, 1 Sulfur-containing alcohols such as 1,2′-thiobis (2-naphthol), 2,2-bis (4-hydroxyethoxyphenyl) propane, 2,2-bis (4-hydroxypropyl) propane, 2, Hydroxy group-containing aromatic compounds such as 2'-bis (hydroxymethyl) diphene oleate ^^, bis (hydroxymethinole) duran, bis (2-hydroxyxenotinole) terephthalate, 2,2—bis (4—hydroxy ethoxy-3 Examples of halogen-containing compounds such as 2,5-bis (bromomethyl) propane and 2,2-bis (bromomethyl) 1-1,3-propanediol Rukoto can, you, alone or in urethane-forming reaction described above can be used in combination of two or more (1) to (2) (meth) Atari rate (a ^1), polyisobutylene Xia sulfonate ( a ² ) and the ratio of the hydroxyl group-containing compound (a ³ ) used are (OH), the number of moles of the hydroxyl group of the (meth) acrylate (a ¹ ) and the number of hydroxyl groups of the hydroxyl group-containing compound (a ³ ). When the number of moles of isocyanate groups in the nate (a ² ) is [NCO], the value of [OH] / [NCO] is usually 1 or more, and this value may be 1 to: I.3. preferable.

When the value of [OH] / [NCO] is less than 1, the releasability at the time of lens molding (molding) is reduced due to the isocyanate groups remaining after the urethanization reaction. And the weather resistance of the finally obtained lens (copolymer) may be impaired. On the other hand, when this value exceeds 1.3, the finally obtained lens (copolymer) tends to have hydrophilicity and water absorption, and the lens does not have sufficient heat resistance.

 The reaction catalyst used in the urethanization reaction of the above (1) and (2) is not particularly limited, such as an amine catalyst, a metal salt catalyst, and an organometallic catalyst. It is preferable to use a highly active organotin catalyst such as acetate or dibutyltin dilaurate.

 [C] The polythiol compound constituting the monomer mixture is a compound having two or more thiol groups in the molecule. Such [C] polythiol compounds include 1,4-bismercaptomethylbenzene, ethanedithiol, 1,4-butanedithiol, ethylene glycol dithioglycolate, 1,2-propanedithiol, bismercaptoethyl sulfide, Bis (mercaptoethylthio) ethane, trimethylolpropanetris (thioglycolate), trimethylolpropanetris (thiopropionate), pentaerythritol tetrakis (thiodalicholate), pentaerythritol tetrakis (thiopropionate), etc. These can be exemplified, and these can be used alone or in combination of two or more.

 The aromatic compound having two or more [D] (meth) acrylic groups (hereinafter also referred to as “[D] component”) constituting the monomer mixture as an optional component includes 2,2-bis (4) —Bisphenol A derivative such as methacryloxyethoxyphenyl) propane, 2,2-bis (3,5-dichloro-4-propmethacryloxyethoxyphenyl) propane, 2,2-bis (3,5-dibromo-4) -Methacryloxyethoxyphenyl) Derivatives of halogen-substituted bisphenol A such as propane, and diphenylfluorene derivatives such as 9,9-bis (4-methacrylic xylethoxyphenyl) fluorene.

By containing the [D] component in the monomer mixture, the moldability (moldability) of the lens can be improved, and the heat resistance and dyeing of the finally obtained lens can be improved. Color properties can be improved.

 The content ratio of [A] component, [B] dibutylbenzene, [C] polythiol compound and [D] component in the monomer mixture is as follows: [[A] component: [B] divinylbenzene: [C] Polythiol compound: [D] component (mass ratio) force is preferably from 10 to 70:10 to 60: 5 to 50: 0 to 30, more preferably a ratio that satisfies the following formula (i). You.

 (i) 1.5 <(a + b + d) / c <3.0

 Here, a: the number of moles of the (meth) acrylic group in the component [A]

 b: [B] Number of moles of a Bier group in divinylbenzene c: [C] Number of moles of a thiol group in a polythiol compound d: Number of moles of a (meth) acryl group in a CD] component

 [A] When the content of the component is less than 10% by mass, it is difficult to control the viscosity of the monomer mixture to a suitable range (35 to 200 cp), and the moldability (moldability) is sufficiently improved. I can't let it. Further, the obtained lens cannot sufficiently satisfy properties such as toughness. On the other hand, when this content ratio exceeds 70% by mass, the viscosity of the monomer mixture becomes excessive, thereby impairing the moldability (moldability) and making it difficult to obtain a lens having a low specific gravity.

 The content of the component (D) is 30% by mass. /. If it exceeds, the effect of introducing a sulfur atom is impaired, the dispersibility is low (abbe number is high), and it is difficult to obtain a lens with a low specific gravity.

 Further, if the value of (a + b + d) Zc is less than 1.5, the finally obtained lens will not have sufficient hardness and heat resistance. On the other hand, if this value exceeds 3.0, the finally obtained lens becomes brittle, and the lens into which a sufficient amount of sulfur atoms has not been introduced has a high refractive index and low dispersibility. It doesn't work.

 Various additives may be contained in the monomer mixture in order to improve the weather resistance, thermal characteristics, and the like of the synthetic resin lens of the present invention.

Examples of such additives include p-tert-butylphenyl salicylate and the like. Benzophenone-based UV absorbers such as 2,4-dihydroxybenzophenone, 2,4-dihydroxybenzophenone, and 2,4-dihydroxybenzophenone; 2- (2,2-hydroxy-3,1-tert.) —Butyl-5,1-methylphenyl) 1-5 monobenzobenzotriazole, 2- (2, -hydroxy-15′-octylphenyl) benzotriazole-based UV absorber such as benzotriazole, etc. 2-ethyl-cyano— UV absorbers based on cyanoacrylates such as 3,3-diphenylacrylate; bis (1,2,2,6,6-pentamethyl-4-piperidyl) sebacate, bis (2,2,6,6-tetramethyl) 4-piperidyl) sebacate, di (1,2,2,6,6-pentamethyl-4-piperidyl) -butyl (3,, 5'-di-tert-butyl-4-hydroxy- Jill) malonate, 1- (2- (3

(3,5-ditert-butylinole-4-hydroxyphenyl) propionyloxy) ethyl) -4- (3- (3,5-ditert-butyl-4-hydroxyphenyl) propionyloxy) 1,2, 2,6,6-tetramethylpiperidine, poly {

(6-{(1,1,3,3-tetramethylbutyl) amino) — 1,3,5-triazine —2,4 diyl) (1,6— {2,2,6,6-tetramethyl — 4—piperidinyl} aminohexamethylene)}, poly {{6— (morpholino) —S—triazine—2,4-diyl} {1,6— (2,2,6,6-tetramethyl—4-piperidyl) ) Amino} hexamethylene), hindered amine-based light stabilizers such as dimethyl succinate polymer with 4-hydroxy-2,2,6,6-tetramethyl-1-piperidinetanol; hindered phenol-based antioxidants Agents, trialkylphosphine-based antioxidants, sulfur-based antioxidants, and the like. It is also possible to add a colorant to adjust the color tone of the lens. The method of preparing the monomer mixture is not particularly limited, but a preferred method is (B) dibutylbenzene in the medium, (meth) and Atari rate (a ^1), polyisobutylene Xia sulfonate (a ²⁾ and by urethanization reaction, or (meth) Atari rate and (a ^1), polyisobutylene Xia sulfonate (a ² ) And a hydroxyl group-containing compound (a ³ ), followed by a urethanation reaction. A mixed system with benzene), and (c) a polythiol conjugate.

[B] Divinylbenzene, [D] Component and various additives may be added and mixed.

 In this method, [B] dibutylbenzene is used as a reaction solvent in the urethanization reaction for producing the [A] component.

 In this way, by using all or part of (B) dibutylbenzene, which is an essential component of the monomer mixture, as the urethanation reaction solvent, there is no need to remove the solvent after the reaction. The preparation process can be simplified.

 Here, [B] divinylbenzene used as a reaction solvent in the urethanization reaction is preferably of high purity, specifically, preferably 80 mass%.

 The reaction temperature of the urethanization reaction is usually 20 to 120 ° C, and preferably 30 to 80 ° C. If the reaction temperature is lower than 20 ° C., the reaction time is undesirably too long, or unreacted isocyanate groups remain. On the other hand, when the reaction temperature exceeds 120 ° C., a polymerization reaction of [B] dibutylbenzene used as a reaction solvent may occur. From the viewpoint of preventing the polymerization of [B] dibutylbenzene during the urethanization reaction, it is preferable to add a polymerization inhibitor to the reaction system. Here, examples of the polymerization inhibitor include dihydroxybenzene and methoxyphenol-phenol-based antioxidants.

 The synthetic resin lens of the present invention comprises the above monomer mixture comprising (A) component, (B) dibutylbenzene and (C) polythiol compound as essential components, and (D) component and various additives as optional components. A monomer composition can be obtained by adding a radical polymerization initiator, and the monomer composition can be produced by subjecting the monomer composition to a polymerization treatment by a cast polymerization method.

 Here, the casting polymerization method involves injecting the monomer composition into a mold or mold (mold) made of glass, plastic, or metal designed to obtain a lens having a desired shape and power. Is polymerized by raising the temperature.

The viscosity of the monomer mixture containing the component (A) is 35 to 200 cp (2 (5 ° C), the sealing material elutes or breaks during casting polymerization of a monomer composition obtained by adding a radical polymerization initiator to this monomer mixture. It can be easily molded (molded) without rubbing.

 Here, examples of the radical polymerization initiator include ordinary organic peroxide-based polymerization initiators. Specifically, tert-butyl peroxy neodecanoate, tert-butylvaloxyvivalate, and tert Peroxyesters such as butyl peroxybenzoate, tert-butynolepoxy-1-2-ethynolehexanoate, tert-butyl benzoyl laurate, tert-butyl peroxy-1,3,5,5-trimethylenolehexanoate Oxides, 3,5,5-trimethylhexanoyl peroxide, and other disilver oxides; 1,1-bis (tert-butyl-butoxy) -1,3,5,5-trimethylcyclo Preferred are peroxy ketals such as hexane. Also, 2,2, -azobis (isobutyronitrile), 2,2, -azobis (2,4-dimethylpareronitrile), 1,1, -azobis (cyclohexane-2-carbonitrile), etc. Are also preferred.

 The monomer composition to be subjected to the polymerization treatment may further contain a polymerization regulator such as 2,4-diphenyl-4-methyl-1-pentene.

 The synthetic resin lens obtained as described above can be subjected to a force grinding process, a polishing process, a dyeing process, a forming process of a hard coat layer, a forming process of an anti-reflection layer, or the like, which can be used as it is.

 The synthetic resin lens of the present invention has a high refractive index (for example, 1.57 or more, further 1.58 or more, especially 1.59 or more), and low light dispersion (for example, an Abbe number of 30 or more). , Especially over 31). Further, the synthetic resin lens of the present invention has a low specific gravity (for example, 1.3 or less) and is excellent in transparency. BEST MODE FOR CARRYING OUT THE INVENTION

Hereinafter, examples of the present invention will be described, but the present invention is not limited thereto. In the following, “parts” means “parts by mass”. <Example 1>

According to the formulation shown in Table 1 below, 24.59 parts of 2-hydroxy-3-phenoxypropyl acrylate [(meth) atalylate (a ')] and m-xylylene diisocyanate [polyisocyanate (a ² )] 10. 41 parts, 10 parts of dibulbenzene, and 0.2 parts of pentaerythritol-tetrakis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate] (antioxidant) Was charged into a reaction vessel, and this was mixed well by stirring. To this system, 0.02 parts of dibutyltin diallate (a urethanization reaction catalyst) was added, and a urethanation reaction (a reaction for producing the component (A)) was performed at 45 ° C for 2 hours.

In this urethanation reaction, when the number of moles of hydroxyl groups of (meth) acrylate (a ¹ ) is [OH] and the number of moles of isocyanate groups of polyisocyanate (a ² ) is [NCO], The value of [OH] / [NCO] is 1.0. After cooling the system to room temperature, 20 parts of divinylbenzene, 35 parts of pentaerythritol tetrakis (thiodalicholate) ([C] polythiol compound), and 2_ (2, -hydroxy-15, -tert-octylphenyl) benztria 0.2 parts of sol (ultraviolet absorber) was added, and the mixture was stirred and mixed to prepare a monomer mixture having a viscosity of 75 cp (25 ° C).

Mol of the content of component [A] in the monomer mixture is 35 weight _^0/0, the number of moles of (meth) acrylic groups of the component [A] a, vinyl Le group of the [B] di Bulle benzene When the number was b and the number of moles of the thiol group of the [C] polythiol compound was c, the value of (a + b) / c was 1.77.

 To this monomer mixture, 0.8 part of tert-butylperoxy-2-ethylhexanoate (radical polymerization initiator) was added, and the mixture was stirred and mixed to prepare a monomer composition.

The joint between the male mold and the female mold constituting the glass mold is sealed with an adhesive tape having an acryl resin adhesive layer, and the monomer composition obtained as described above is placed in the cavity of the glass mold. After the material was injected and kept at 45 ° C for 8 hours, the temperature was raised to 80 ° C over 4 hours, and further raised to 120 ° C over 2 hours. 120 ° C , And cooled to 70 ° C, and the glass mold was peeled off to obtain a colorless and transparent lens (the synthetic resin lens of the present invention).

 The refractive index of this lens was as high as 1.596, and the Abbe number was 37 with low light dispersion. The specific gravity was 1.27, which was light.

 When the lens was stained for 10 minutes in a brown staining bath for CR-39, the light transmittance decreased from 87% to 42%.

 The results are shown in Table 2 below.

<Example 2>

According to the formulation shown in Table 1 below, 6.1 parts of 2-hydroxy-3-phenoxypropyl acrylate [(meth) acrylate (a ¹ )] and m-xylylene diisocyanate [polyisocyanate ( a ² )] 5.2 parts and 2,2-bis (4-hydroxyethoxy-3,5-dibromophenyl) propane [hydroxyl-containing compound (a ³ )] 8.7 parts and dibutylbenzene 15 parts and 0.3 part of 2,4-difluoro-4-methyl-1-pentene (polymerization regulator) were charged in a reaction vessel, and they were mixed well by stirring. To this system, 0.02 parts of dibutyltin dilaurate (a urethanization reaction catalyst) was added, and a urethanization reaction (reaction of component [A], J) was carried out at 50 ° C for 1.5 hours.

In this urethanization reaction, (meth) Akurireto _(a ') and a hydroxyl-containing organic compound (a ³⁾ [OH] to the number of moles of hydroxyl groups in, polyisobutylene Xia sulfonate (a

^When the monole number of the isocyanate group of ² ) is [NCO], the value of [OH] / [NCO] is 1.0. .

 After cooling this system to room temperature, 16.3 parts of divinylbenzene and pentaerythritol tetrakis (thiopropionate) ([C] polythiol compound)

34. 9 parts, 2,2-bis (4-methacryloxyethoxypheninole) propane (CD) component) 13. 8 parts, 2- (2'-hydroxy-5'-tert-octylphenyl) benzotriazole (UV absorber) 0.2 parts and 1,3,5-tris (3,5-ditert-butyl-4-hydroxybenzyl-S-triazine-2,4,6-trione (antioxidant Agent) and mix with stirring As a result, a monomer mixture having a viscosity of 80 cp (25 ° C.) was prepared.

 In the monomer mixture, the content of the component [A] is 20% by mass, [a] is the number of moles of the (meth) acrylic group of the component A3, and [B] is the number of moles of the vinyl group of dibutylbenzene. , [C] the number of moles of the thiol group of the polythiol compound is c

The value of (a + b + d) / c was 1.99, where d is the number of moles of the (meth) acryl group contained in the [D] component.

 To this monomer mixture, 0.6 part of 1,1, -azobis (cyclohexane-11-carbonitrile) (radical polymerization initiator) is added, and the mixture is stirred and mixed to obtain a monomer composition. Prepared.

 The joint between the male mold and the female mold constituting the glass mold is sealed with an adhesive tape having an acryl resin adhesive layer, and the monomer obtained as described above is placed in the cavity of the glass mold. After injecting the composition and keeping it at 60 ° C for 8 hours, the temperature was raised to 95 ° C over 4 hours, and further raised to 130 ° C over 2 hours. After maintaining at 130 ° C for 1 hour, the temperature was cooled to 70 ° C and the glass mold was peeled off to obtain a colorless and transparent lens (the synthetic resin lens of the present invention).

 The refractive index of this lens was as high as 1.597, and the Abbe number was 36 with low light dispersion. The specific gravity was as light as 1.25.

 When the lens was stained for 10 minutes in a CR-39 brown staining bath, the light transmittance decreased from 87% to 35%.

 The results are shown in Table 2 below.

Example 3>

According to the formulation shown in Table 1 below, 2-hydroxy-3-phenoxypropyl acrylate [(meth) atalylate (a ¹ )] 28.6 parts and a trimer of hexamethylene diisocyanate [polyisocyanate] (A ² )] 16.4 parts, dibininole benzene 15 parts, pentaerythritol-tetrakis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate] (antioxidant) 0.2 parts Was charged into a reaction vessel, and this was mixed well by stirring. To this system, add 0.02 parts of dibutyltin dilaurate (an urethane-forming hornworm medium), and incubate at 45 ° C for 2 hours. Urethanization reaction (reaction for the formation of component [A]).

In this urethanation reaction, when the number of moles of hydroxyl groups of (meth) acrylate (a ¹ ) is [OH] and the number of moles of isocyanate groups of polyisocyanate (a ² ) is [NCO], The value of [OH] / [NCO] is 1.3. After cooling this production system to room temperature, 18 parts of jibirubenzene, 22 parts of bismercaptoethyl sulfide ([C] polythiol compound), and 2- (2, -hydroxy) 5'-tert-octylphenyl 0.2 parts of benzotriazole (ultraviolet absorber) was added and mixed with stirring to prepare a monomer mixture having a viscosity of 60 cp (25 ° C.).

The number of moles of the content of component [A] in the monomer mixture has a 45 mass ⁰ I component [A] (meth) acryl group a, the number of moles of vinyl Le groups of (B) di Bulle benzene b, [C] The value of (a + b) / c was 2.23, where c is the number of moles of the thiol group in the polythiol compound.

 0.8 parts of tert-butylperoxy-2-ethylhexanoate (radical polymerization initiator) was added to the monomer mixture, and the mixture was stirred and mixed to prepare a monomer composition.

 The joint between the male and female molds constituting the glass mold is sealed with an adhesive tape having an acrylic resin-based adhesive layer, and the monomer composition obtained as described above is placed in the cavity of the glass mold. After the material was injected and kept at 45 ° C for 8 hours, the temperature was raised to 80 ° C over 4 hours, and further raised to 120 ° C over 2 hours. After holding at 120 ° C for 1 hour, the temperature was cooled to 70 ° C and the glass mold was peeled off to obtain a colorless and transparent lens (the synthetic resin lens of the present invention).

 The refractive index of this lens was as high as 1.598, and the Abbe number was 35 with low light dispersion. The specific gravity was as light as 1.21.

 When this lens was stained for 10 minutes in a brown staining bath for CR-39, the light transmittance decreased from 87% to 28%.

 The results are shown in Table 2 below.

<Comparative Example 1> According to the formulation shown in Table 1 below, 52 parts of biebibenzene, 8 parts of pentaerythritol-letetrakis (thiopropionate), and 2 parts of 2- (2, -hydroxy-5, -tert-octylphenyl) benztriazole (ultraviolet absorption) 0.2 part) was charged into a reaction vessel and mixed well with stirring to prepare a monomer mixture having a viscosity of 15 cp (25 ° C.).

 This monomer mixture does not contain the component (A), and the number of moles of the butyl group of dibutylbenzene is b, and the number of moles of the thiol group of pentaerythritol tetrakis (thiopropionate) is c. The value of b / c was 2.03.

 To this monomer mixture was added 0.8 parts of tert-butyl xy-2-ethylhexanoate (radical polymerization initiator), and the mixture was stirred and mixed to prepare a monomer composition. did.

 The joint between the male mold and the female mold constituting the glass mold is sealed with an adhesive tape having an acryl resin adhesive layer, and the monomer composition obtained as described above is placed in the cavity of the glass mold. After injecting the substance and keeping it at 45 ° C for 8 hours, the temperature was raised to 80 ° C over 4 hours, and then raised to 120 ° C over 2 hours. And the monomer composition leaked out of the glass mold. When the same operation was repeated 10 times, the monomer composition leaked out seven times before the polymerization reaction was completed. For three of the ten times, the temperature was raised to 120 ° C, held at 120 ° C for one hour, cooled to 70 ° C, the glass mold was peeled off, and the lens was removed. Obtained. When the obtained lenses were observed, cloudiness was observed at each peripheral portion.

The results are shown in Table 2 below. Example Example Example Comparative example

 1 2 3 1

a ¹ 2—Hydroxy-1-3-phenoxypropyl acrylate 24.59 6.1 28.6

 [A] m-xylylene diisocyanate 10.41 5.2

Simple a ²

 Hexamethylene diisocyanate trimer 16.4

The amount min a ³ 2, 2-bis (4-hydroxyethoxy 8.7

 -3,5-dibromophenyl) propane

Dibutyltin dilaurate (catalyst for urethanization reaction) 0.02 0.02 0.02

 [B] Divinylbenzene (Amount used as reaction solvent + amount added) 30 31.3 33 52

Mixed

 [C] Pentaerythritol Thorte Trakis (thiodarycolate) 35

CC) Pentaerythritol tetrakis (thiopropionate) 34.9 48

 t

[C] Bismercaptoethyl sulfide 22

object

 CD) 2, 2--Bis (4-methacrylic acid chethetoxyphenyl) propane 13.8

 Penyu Erythri Thor-Tetrakis [3- (3,5-G-0.2 0.2

 tert-butyl-1-4-hydroxypropyl) propionate]

 2-(2'-hydroxy-5'-ter octylphenyl) 0.2 0.2 0.2 0.2

 Benztriazole (UV absorber)

 2,4--diph j: 2-ru 4-methyl-1-pentene (polymerization regulator) 0.3

 1,3,5—tris (3,5—di t er t—butyl 4—0.2

 Hydroxybenzyl-S-triazine-2,4,6-trione

 t e r t--Butyl butyl-2- (ethylhexanoate) 0.8 0.8 0.8

Initiator 1, Γ-azobis (cyclohexane-111-carbonitrile) 0.6

Example Example Example Comparative example

 1 2 3 1

Viscosity of monomer mixture (25 ° C) Ccp 75 80 60 15

Ratio of component [A] in monomer mixture [% by mass] 35 20 450

The value of the expression (i) [(a + b + d) / c] 1.77 1.99 2.23 2.03

Refractive index 1.596 1.597 1.598

Abbe number 37 36 35

Specific gravity 1.27 1.25 1.21

Light transmittance Before staining 87 87 87

 (%)

 After staining 42 35 28

¾2 Example 4>

2- arsenide Dorokishi 3 phenoxyethanol propyl § chestnut rate and [(meth) Atari rate (a ')] 11.55 parts, m- xylylene iso Xia sulphonate [Poriisoshia sulfonate (a ^2)] 9.87 parts If, 2, 2- bis (4-hydroxycarboxylic ethoxy one 3, 5-dibromo-phenylalanine) propane [hydroxyl group-containing compound (a ^3)] 16. and 57 parts, and 25 parts of divinylbenzene, Pentaerisuri tall chromatography tetrakis [ 3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate] (antioxidant) 0.2 part was charged into a reaction vessel and mixed well with stirring. To this system, 0.22 parts of dibutyltin dilaurate (a urethanization reaction catalyst) was added, and a urethanization reaction (a reaction for producing the component (A)) was performed at 40 ° C. for 3 hours.

In this urethanization reaction, (meth) Atari rate (a ¹⁾ and a hydroxyl-containing organic compound (a ³⁾ [OH] to the number of moles of hydroxyl groups in, for Isoshiane one bets group of the polyisobutyl Xia sulfonate (a ²⁾ When the number of moles is [NCO], the value of [OH] / [NCO] is 1.0.

 After the production system was cooled to room temperature, 7 parts of dibutylbenzene, 30 parts of pentaerythritol tetrakis (thiodalicholate) ([C] polythioly bonded compound), and 2- (2, -hydroxy-5,1-tert.) 0.2 part of octynolephenyl) benztriazole (ultraviolet absorber) was added to the mixture, and the mixture was stirred and mixed to prepare a monomer mixture having a viscosity of 40 cp (25 ° C). .

The content of component [A] in the monomer mixture has a 38 mass ⁰ I component [A] (meth) a number of moles of acrylic group, the number of moles of vinyl Le groups of (B) di Bulle benzene b, [C] When the number of moles of the thiol group in the polythiol compound is c, the value of (a + b) Zc was 1.96.

 To this monomer mixture, 0.8 part of t-tert-butylhydroxy-12-ethylhexanoate (radical polymerization initiator) was added, and the mixture was stirred and mixed to prepare a monomer composition.

The joint between the male mold and the female mold making up the glass mold is sealed with an adhesive tape having an ataryl resin-based adhesive layer. After injecting the monomer composition obtained as described above and maintaining at 45 ° C for 8 hours, the temperature is raised to 75 ° C over 4 hours, and further raised to 120 ° C over 2 hours. Was. After holding at 120 ° C for 1 hour, the temperature was cooled to 70 ° C and the glass mold was peeled off to obtain a colorless and transparent lens (the synthetic resin lens of the present invention).

 The refractive index of this lens was as high as 1.597, and the Abbe number was 33 with low light dispersion. The specific gravity was as light as 1.22.

 When this lens was stained for 10 minutes in a brown staining bath for CR-39, the light transmittance decreased from 87% to 33%.

Example 5>

And 2 heat Dorokishi one 3 phenoxyethanol propyl Atari rate [(meth) Akuri rate (a ^1)] 21.02 parts of a m-xylylene iso Xia sulphonate [Poriisoshia sulfonate (a ^2)] 8.98 parts of di 24 parts of benzene and 0.2 part of 2,4-diphenyl-4-methyl-1-pentene (polymerization regulator) were charged in a reaction vessel, and mixed well with stirring. To this system, 0.02 parts of dibutyltin dilaurate (a urethanization reaction catalyst) was added, and a urethanization reaction (a reaction for producing the component (A)) was carried out at 40 ° C. for 3 hours.

In this urethanation reaction, when the number of moles of hydroxyl groups in (meth) acrylate (a ¹ ) is [OH] and the number of moles of isocyanate groups in polyisocyanate (a ² ) is [NCO] The value of [OH] / [NCO] is 1.0. After cooling this production system to room temperature, 26 parts of pentaerythritol tetrakis (thiop mouth pionate) ([C] polythiol compound) and 2,2 bis (4-methacryloxyethoxyphenyl) propane ([D] component) 20 parts, 2- (2, -hydroxy-5, -tert-octylphenyl) benzotriazole (ultraviolet absorber) ◦. 2 parts, 1,3,5-tris (3,5 ditertbutyl-4H Droxybenzyl-S triazine 2,4,6 trione (antioxidant) 0.2 part was added to the mixture, and the mixture was stirred and mixed to obtain a monomer mixture having a viscosity of 60 cp (25 ° C). Prepared.

The content of the component [A] in the monomer mixture is 30% by mass, and the content of the component [A] (A) The number of moles of the (meth) acrylic group is a, [B] The number of moles of the vinyl group of dibutylbenzene is b, and [C] The number of moles of the thiol group of the polythiol compound is c. (Meta) Assuming that the number of monoles of the acrylic group is d, the value of (a + b + d) / c was 2.59.

 To this monomer mixture, 0.8 part of 1,1, -azobis (cyclohexane-11-carbonitrile) (radical polymerization initiator) is added, and the mixture is stirred and mixed to form a monomer composition. Prepared.

 The joint between the male mold and the female mold that constitute the glass monoredo is sealed with an adhesive tape having an acryl resin adhesive layer, and the monomer composition obtained as described above is placed in the cavity of the glass mold. Was injected and maintained at 55 ° C. for 10 hours, then heated to 80 ° C. over 4 hours, and further raised to 130 ° C. over 2 hours. After holding at 130 ° C for 1 hour, the temperature was cooled to 70 ° C and the glass mold was peeled off to obtain a colorless and transparent lens (the synthetic resin lens of the present invention).

 This lens had a high refractive index of 1.57, an Abbe number of 36, and low light dispersion. The specific gravity was 1.22, which was light.

 When this lens was stained with a brown dyeing bath for CR-39 for 10 minutes, the light transmittance decreased from 88% to 57%. The invention's effect

 The lens according to the present invention has a high refractive index and low power, light and light dispersion. Further, the lens according to the present invention has a low specific gravity and is excellent in transparency.

 Further, when the lens of the present invention is molded by the casting polymerization method, the sealing material can be easily molded without being eluted or damaged.

Claims

 The scope of the claims  [1] [A] A monomer mixture containing a polyfunctional (meth) acrylate having a urethane bond, [B] divinyl benzene, and [C] a polythiol compound is polymerized using a radical polymerization initiator. A synthetic tree lens obtained by: [2] [A] A polyfunctional (meth) acrylate having a urethane bond is composed of a (meth) acrylate (a ') having a hydroxyl group in the molecule and a polyisocyanate having two or more isocyanate groups in the molecule. ^2. The synthetic resin lens according to claim 1, wherein the synthetic resin lens is obtained by reacting the compound with a nate (a ² ). [3] [A] A polyfunctional (meth) acrylate having a urethane bond is a (meth) acrylate having a hydroxyl group in the molecule (a ¹ ) and a polyiso having two or more isocyanate groups in the molecule. Cyanate (a ² ) and The (meth) Atari rate (a ') [OH] to the number of moles of hydroxyl groups in, when the Monore number of Isoshianeto groups of the polyisobutylene Xia sulfonate (a ²⁾ and [NCO], [OH] / [ 2. The synthetic resin lens according to claim 1, wherein the synthetic resin lens is obtained by reacting at a ratio at which the value of [NCO] is 1 or more. [4] [A] A polyfunctional (meth) acrylate having a urethane bond is a (meth) acrylate having a hydroxyl group in the molecule (a ¹ ) and a polyiso having two or more isocyanate groups in the molecule. Cyanate (a ² ) and When the number of moles of hydroxyl groups of the (meth) acrylate (a ¹ ) is [OH] and the number of moles of isocyanate groups of the polyisocyanate (a ² ) is [NCO], [OH] / [ 2. The synthetic resin lens according to claim 1, wherein the synthetic resin lens is obtained by reacting at a ratio of NCO] of 1 to 1.3. [5] [A] A polyfunctional (meth) acrylate having a urethane bond is composed of a (meth) acrylate (a ') having a hydroxyl group in a molecule and a polyiso (a) having two or more isocyanate groups in a molecule. synthetic resin lenses according to claim 1, wherein the Shianeto and (a ²⁾ is obtained by reacting in the presence of a highly active organic tin catalyst. [6] [A] A polyfunctional (meth) acrylate having a urethane bond is composed of a (meth) acrylate (a ') having a hydroxyl group in the molecule, and a polyiso having two or more isocyanate groups in the molecule. and Shianeto (a ^2), a compound having two or more hydroxyl groups in the molecule (a ¹⁾ and wherein the synthetic resin lens in claim 1, characterized in that is obtained by reacting. [7] [A] A polyfunctional (meth) acrylate having a urethane bond is a (meth) acrylate having a hydroxyl group in the molecule (a ¹ ) and a polyiso having two or more isocyanate groups in the molecule. A cyanate (a ² ) and a compound (a ¹ ) having two or more hydroxyl groups in the molecule, The number of moles of hydroxyl groups of the (meth) acrylate (a ¹ ) and the compound (a ³ ) is [OH], and the number of moles of isocyanate groups of the polyisocyanate (a ² ) is [NCO]. 2. The synthetic resin lens according to claim 1, wherein the synthetic resin lens is obtained by reacting at a ratio of [OH] / [NCO] being 1 or more. [8] [A] A polyfunctional (meth) acrylate having a urethane bond is a (meth) acrylate having a hydroxyl group in the molecule (a ¹ ) and a polyiso having two or more isocyanate groups in the molecule. A cyanate (a ² ) and a compound having two or more hydroxyl groups in the molecule (a ³ ) The number of moles of hydroxyl groups of the (meth) acrylate (a ¹ ) and the compound (a ³ ) is [OH], and the number of moles of isocyanate groups of the polyisocyanate (a ² ) is [NCO]. 2. The synthetic resin lens according to claim 1, wherein the lens is obtained by reacting at a ratio of [OH] / [NCO] of 1 to: I.3. [9] [A] A polyfunctional (meth) acrylate having a urethane bond is composed of a (meth) acrylate (a ') having a hydroxyl group in the molecule and a polyisocyanate having two or more isocyanate groups in the molecule. and sulfonates (a ^s), wherein the is obtained by I匕合product having two or more hydroxyl groups and (a ³⁾ is reacted in the presence of a highly active organic tin catalyst in the molecule The synthetic resin lens according to claim 1. [10] [A] a polyfunctional (meth) acrylate having a urethane bond, [B] divinylbenzene, [C] a polythiol compound, and [D] an aromatic compound having two or more (meth) acryl groups. A synthetic resin lens obtained by polymerizing a monomer mixture using a radical polymerization initiator. [11] [A] Mass ratio of polyfunctional (meth) acrylate having urethane bond, [B] divinylbenzene, [C] polythiol compound, and [D] aromatic compound having two or more (meth) acrylic groups From 10 to 70: 10 to 60: 5 to 50: 0 to 30 by polymerization using a radical polymerization initiator. A synthetic resin lens, characterized in that:  [12] [A] A polyfunctional (meth) acrylate having a urethane bond, [B] divinyl benzene, [C] a polythiol compound, and [D] an aromatic compound having two or more (meth) acryl groups are represented by the following formula: A synthetic lens which is obtained by polymerizing, using a radical polymerization initiator, a monomer mixture containing (i) in a ratio that satisfies (i).  Formula (i) 1.5 (a + b + d) Zc 3.0  Here, a: [A] the number of moles of the (meth) acryl group of the polyfunctional (meth) acrylate having a urethane bond  b: [B] The number of moles of the butyl group of dibutylbenzene c: [C] The number of moles of the thiol group of the polythiol compound d: CD] The aromatic compound having two or more (meth) acrylic groups. Meth) Number of moles of acrylic group  [13] [A] A monomer mixture containing a polyfunctional (meth) atalylate having a urethane bond, [B] divinylbenzene and [C] a polythiol compound is polymerized using a radical polymerization initiator. A method for producing a synthetic resin lens, comprising: And [14] having a hydroxyl group in the molecule (meth) Akurireto (a ^1), by reacting a polyisobutylene Xia sulfonates having two or more iso Shianeto groups in the molecule (a ²⁾ a [A] urethane bonds Preparing polyfunctional (meth) acrylates having 14. The method for producing a synthetic resin lens according to claim 13, wherein the obtained monomer mixture containing the polyfunctional (meth) acrylate which has a urethane bond is polymerized. [15] a (meth) acrylate (a ′) having a hydroxyl group in the molecule and a polyisocyanate (a ² ) having two or more isocyanate groups in the molecule, When the number of moles of hydroxyl groups of the (meth) acrylate (a ¹ ) is [OH] and the number of moles of isocyanate groups of the polyisocyanate (a ² ) is [NCO], [OH] / [ [A] A polyfunctional (meth) acrylate having a urethane bond is prepared by reacting at a ratio where the value of [NCO] is 1 or more.  14. The method for producing a synthetic resin lens according to claim 13, wherein the obtained monomer mixture containing the polyfunctional (meth) acrylate having a [A] urethane bond is polymerized. [16] a (meth) acrylate having a hydroxyl group in the molecule (a ¹ ) and a polyisocyanate having two or more isocyanate groups in the molecule (a ² ) When the number of moles of the hydroxyl group of the (meth) acrylate (a ¹ ) is [OH] and the number of moles of the isocyanate group of the polyisocyanate (a ² ) is [NCO], [〇H] / [A] A polyfunctional (meth) acrylate having a urethane bond was prepared by reacting at a ratio such that the value of [NCO] was 1 to 1.3, and the obtained [A] polyfunctional (U) having a urethane bond was obtained. 14. The method for producing a synthetic resin lens according to claim 13, wherein a monomer mixture containing (meth) acrylate is polymerized. (17) and having a hydroxyl group in the molecule (meth) Atari rate (a ^1), polyisobutylene Xia sulfonates having two or more iso Shianeto groups in the molecule (a ²⁾ and a high activity of organic scan's catalyst By reacting in the presence of [A] to prepare a polyfunctional (meth) atalylate having a urethane bond, 14. The method for producing a synthetic resin lens according to claim 13, wherein the obtained monomer mixture containing the polyfunctional (meth) acrylate which has a urethane bond is polymerized. [18] (meth) acrylate (a ′) having a hydroxyl group in the molecule, polyisocyanate (a ² ) having two or more isocyanate groups in the molecule, and a compound having two or more hydroxyl groups in the molecule (a ³⁾ and the polyfunctional (meth) Atari rate with (a) a urethane bond by reacting prepared,  14. The method for producing a synthetic resin lens according to claim 13, wherein the obtained monomer mixture containing the polyfunctional (meth) acrylate which has a urethane bond is polymerized. [19] (meth) atalylate (a ¹ ) having a hydroxyl group in the molecule, polyisocyanate (a ² ) having two or more isocyanate groups in the molecule, and two or more hydroxyl groups in the molecule Compound (a ³ ) and The number of moles of hydroxyl groups of the (meth) acrylate (a ¹ ) and the compound (a ³ ) is [OH], and the number of moles of isocyanate groups of the polyisocyanate (a ² ) is [NCO]. At this time, [A] a polyfunctional (meth) acrylate having a urethane bond is prepared by reacting at a ratio such that the value of [OH] Z CNCO becomes 1 or more,  14. The method for producing a synthetic resin lens according to claim 13, wherein the obtained monomer mixture containing the polyfunctional (meth) acrylate which has a urethane bond is polymerized. [20] (Meth) acrylate (a ′) having a hydroxyl group in the molecule, polyisocyanate (a ² ) having two or more isocyanate groups in the molecule, and a compound having two or more hydroxyl groups in the molecule (a. ³ ) and When the number of moles of hydroxyl groups of the (meth) acrylate (a ¹ ) and the compound (a ³ ) is [OH], and the number of moles of isocyanate groups of the polyisocyanate (a ² ) is [NCO]. , [OH] / [NCO] values are :! (A) Polyfunctional (meth) acrylate having a urethane bond is prepared by reacting at a ratio of 14. The synthetic resin resin according to claim 13, wherein the obtained monomer mixture containing [A] a polyfunctional (meth) acrylate having a urethane bond is polymerized. Production method. [21] (meth) acrylate having a hydroxyl group in the molecule (a ¹ ), polyisocyanate having two or more isocyanate groups in the molecule (a ² ), and having two or more hydroxyl groups in the molecule compound and (a ³⁾ to prepare a polyfunctional (meth) Atari rate with (a) a urethane bond by reacting in the presence of a highly active organic tin catalyst,  14. The method for producing a synthetic resin lens according to claim 13, wherein the obtained monomer mixture containing the [A] polyfunctional (meth) acrylate having a urethane bond is polymerized. [22] (B) Urethane formation in dibutylbenzene with (meth) acrylate (a ¹ ) having a hydroxyl group in the molecule and polyisocyanate (a ² ) having two or more isocyanate groups in the molecule By reacting, a mixed system of [A] a polyfunctional (meth) acrylate having a urethane bond and [B] dibutylbenzene is prepared, and [C] a polythiolic compound is added to the mixed system. 14. The method for producing a synthetic resin lens according to claim 13, wherein a monomer mixture is prepared by mixing and mixing, and the monomer mixture is polymerized using a radical polymerization initiator. [23] (Meth) acrylate having a hydroxyl group in the molecule (a ¹ ), polyisocyanate having two or more isocyanate groups in the molecule (a ² ), and having two or more hydroxyl groups in the molecule the compound (a ³⁾ and thereby urethanes reaction in the [B] in divinylbenzene, to prepare a mixed system of a polyfunctional (meth) Akuri rate and (B) di Bulle benzene having (a) a urethane bond Adding a (C) polythiol compound to the mixture and mixing to prepare a monomer mixture, and polymerizing the monomer mixture using a radical polymerization initiator. 13. The method for producing a synthetic resin lens according to item 13. [24] [A] Polyfunctional (meth) atalylate having a urethane bond, [B] divinylbenzene, [C] polythiol compound, and [D] an aromatic compound having two or more (meth) acryl groups. A method for producing a synthetic resin lens, comprising polymerizing a monomer mixture obtained by using a radical polymerization initiator. [25] [A] Polyfunctional (meth) acrylate having a urethane bond, [B] divinyl benzene, [C] polythiol compound, and [D] an aromatic compound having two or more (meth) acryl groups in mass ratio. It is characterized in that a monomer mixture containing 10 to 70: 10 to 60: 5 to 50: 0 to 30 is polymerized using a radical polymerization initiator. A method for manufacturing a synthetic resin lens.  [26] [A] Polyfunctional (meth) atalylate having urethane bond, [B] divinyl benzene, [C] polythiol compound, and [D] aromatic compound having two or more (meth) acrylic groups are as follows. A method for producing a synthetic resin lens, comprising polymerizing a monomer mixture containing a ratio satisfying the formula (i) using a radical polymerization initiator.  Formula (i) 1.5 <(a + b + d) Zc <3.0  Here, a: [A] The number of moles of the (meth) acryl group of the polyfunctional (meth) acrylate having a urethane bond  b: [B] Number of moles of the butyl group of dibutylbenzene c: [C] Number of moles of the thiol group of the polythiol compound d: [D] Of the aromatic compound having two or more (meth) acrylic groups ( Meth) Number of moles of acrylic group [27] A (meth) acrylate having a hydroxyl group in the molecule (a ¹ ) and a polyisocyanate having two or more isocyanate groups in the molecule (a ² ) [B] Urethane reaction in dibutylbenzene Thus, a mixed system of [A] a polyfunctional (meth) acrylate having a urethane bond and [B] dibutylbenzene is prepared, and [C] a polythiol compound and [D] ( (Meth) A monomer mixture is prepared by adding and mixing with an aromatic compound having two or more acrylic groups, and the monomer mixture is polymerized using a radical polymerization initiator. A method for producing the synthetic resin lens according to claim 24. [28] (Meth) acrylate (a ′) having a hydroxyl group in the molecule, polyisocyanate (a ² ) having two or more isocyanate groups in the molecule, and two or more hydroxyl groups in the molecule urethane in the compound (a ³⁾ and (B) in di Bulle benzene A mixed system of [A] a polyfunctional (meth) acrylate having a urethane bond and [B] divinylbenzene is prepared by the polymerization reaction, and [C] a polythiol compound and [D] A monomer mixture is prepared by adding and mixing an aromatic compound having two or more (meth) acrylic groups, and the monomer mixture is polymerized using a radical polymerization initiator. 25. The method for producing a synthetic resin lens according to claim 24.