JP2009226742A - Manufacturing method of plastic lens - Google Patents

Abstract

Provided is a method of manufacturing a plastic lens having a practical productivity and capable of obtaining a thick plastic lens free from optical distortion and striae.
The method for producing a plastic lens according to the present invention includes a filling step of filling a polymerizable mold with a polymerizable composition, and a curing step of curing the polymerizable composition by exposing the mold under a predetermined temperature condition. A curing step in which, after the filling step, the polymerizable composition is maintained at an initial temperature or higher during the filling step, and after the holding step, the polymerizable composition And a cooling step for cooling.
[Selection] Figure 1

Description

  The present invention relates to a method for manufacturing a plastic lens.

A plastic lens is lighter than a glass lens, and has various merits such as good moldability and workability, being hard to break and having high safety. For this reason, it is widely used in fields such as eyeglass lenses and camera lenses.
At first, plastic lenses with a refractive index of 1.50 were widely used, but in recent years, development of plastic lenses with a high refractive index has been promoted, and polythiourethane materials have been proposed (for example, Patent Literatures 1 to 3).

  These plastic lenses have been developed for the purpose of realizing a thin spectacle lens with a high refractive index, but are beginning to be studied for correcting amblyopia, which was difficult to cope with with conventional spectacle lenses. For such applications, a thick plastic lens with a high refractive index is desired.

Japanese Patent Laid-Open No. 2-270859 JP 7-252207 A JP 2001-342252 A

However, thick plastic lenses have the following problems.
A plastic lens is usually formed by polymerizing and curing a polymerizable composition filled in a mold, but since the polymerization rate of the polymerizable composition varies depending on the temperature, a slight temperature distribution is locally present. Increase or decrease the polymerization rate.
For this reason, for example, the part where the polymerization rate is increased has a molecular weight higher than that of the others and settles downward or rises upward. Further, convection of the polymerizable composition may occur in the molding mold. If the polymerizable composition is cured with these traces remaining, optical distortion or striae may occur in the plastic lens.

Here, when a thick plastic lens is to be formed, it is difficult to uniformly heat the polymerizable composition so as not to cause a temperature distribution. In addition, since a large amount of the polymerizable composition is polymerized, the polymerizable composition itself generates heat of polymerization reaction, which may cause temperature distribution.
For this reason, when trying to form a thick plastic lens, defects such as optical distortion are likely to occur.

On the other hand, in order to suppress the occurrence of optical distortion or the like, a method is known in which polymerization is advanced slowly and slowly at low temperatures so that the reaction proceeds as uniformly as possible.
However, this method increases the time required for polymerization and curing, leading to a decrease in productivity.
Moreover, since the low-temperature polymerizable composition has a high viscosity, it may be difficult to fill the molding mold, or unevenness of the polymerizable composition generated at the time of filling may remain as a defective appearance of the plastic lens.

  SUMMARY OF THE INVENTION Accordingly, the present invention has an object to provide a method for manufacturing a plastic lens that solves such conventional problems and has a practical productivity and can provide a thick plastic lens without optical distortion or striae. And

  The method for producing a plastic lens of the present invention includes a filling step of filling a polymerizable composition into a molding mold, and a curing step of curing the polymerizable composition by exposing the molding mold under a predetermined temperature condition. A method for producing a plastic lens, wherein the curing step includes a holding step of maintaining the polymerizable composition at an initial temperature or higher during the filling step after the filling step, and a polymerization step after the holding step. And a cooling step for cooling the sex composition.

In general, the polymerization rate is slow at the beginning of the reaction, but rapidly increases at a certain stage. When the polymerization rate increases, problems such as optical distortion are likely to occur.
In the present invention, it is possible to prevent the local increase in the polymerization rate by performing the cooling step before the rapid increase in the polymerization rate occurs and lowering the temperature of the polymerizable composition.
Thereby, even when a thick plastic lens is formed, it is possible to suppress the occurrence of defects such as optical distortion and striae.

On the other hand, in the holding step corresponding to the initial stage of polymerization and curing, which is less likely to cause problems, the polymerizable composition is held at a relatively high initial temperature or higher, and the polymerization proceeds to some extent.
For this reason, in the manufacturing method of the present invention, the time required for manufacturing the plastic lens is dramatically reduced as compared with the conventional manufacturing method in which the polymerizable composition is kept at a low temperature from the initial stage of the polymerization curing in order to ensure the uniformity of the polymerization. It can be shortened.

In addition, since the holding process is carried out following the filling process, it is not necessary to keep the polymerizable composition at a low temperature from the stage of the filling process. Therefore, if the initial temperature is set so that the viscosity of the polymerizable composition becomes moderate, the polymerizable composition can be easily filled into the molding mold, and unevenness does not occur during filling.
Furthermore, when a low-temperature polymerizable composition is filled in a high-temperature molding mold, the molding mold may shrink and the polymerizable composition may leak or bubbles may be generated, but in the present invention, the initial temperature is lowered. Since there is no need to set, such a problem does not occur.
Therefore, according to the present invention, a thick plastic lens free from optical distortion or striae can be manufactured easily and in a short time.

In the method for producing a plastic lens of the present invention, it is preferable that the cooling step is performed before the polymerizable composition is gelled.
During the progress of gelation of the polymerizable composition, a local increase in the polymerization rate tends to occur.
On the other hand, in the present invention, since the cooling step is performed before gelation, it is possible to prevent a local increase in the polymerization rate and reliably prevent the occurrence of optical distortion and striae.
In addition, the gelation in this invention shows the state which the polymerization reaction of the polymeric composition advanced, the viscosity rose and the fluidity | liquidity was lose | eliminated. If the standard of gelation is shown by a viscosity, it will be 10000000 mPa * s (10 kPa * s) or more, for example.

In the method of manufacturing a plastic lens of the present invention, when the time from the start to the end of the curing step is 100%, the cooling step is a time when 15% or more and 80% or less has elapsed from the start of the holding step. Is preferably carried out in
According to such a configuration, it is possible to carry out the cooling step before the start of gelation while proceeding the polymerization in the holding step to shorten the production time.

  Here, it is not preferable that the cooling process is performed at a point of less than 15% from the start of the holding process because the holding process is too short and the effect of shortening the manufacturing time is reduced. On the other hand, if it exceeds 80%, the gelation starts before the cooling step, and optical distortion or striae may occur, which is not preferable.

In addition, when the polymerizable composition contains a compound having a thioepoxy group or an epoxy group, the cooling step is more preferably performed at a time of 20% or more and 80% or less from the start of the holding step.
In addition, the cooling step is carried out by using an inorganic compound (A) in which the polymerizable composition has at least one of a sulfur atom and a selenium atom, a compound (B) represented by the following formula (1), a thiol ( SH) When the compound (C) having one or more groups is contained, it is more preferably 20% or more and 80% or less from the start of the holding step.

In addition, when the polymerizable composition contains at least one of a polyisocyanate compound and a polyisothiocyanate compound and at least one of a polyol compound and a polythiol compound, the cooling step is performed by 50% or more from the start of the holding step. More preferably, the time is less than or equal to%.
In addition, when the polymerizable composition contains a compound having at least one of an acryl group, a methacryl group, and an allyl group, the cooling step may be performed at a time of 30% to 70% from the start of the holding step. More preferred.

The method for producing a plastic lens of the present invention preferably includes a low temperature maintaining step for maintaining the temperature of the cooled polymerizable composition after the cooling step.
According to such a configuration, the temperature of the polymerizable composition can be kept at a low temperature while the gelation proceeds by the low temperature maintaining step, so that the occurrence of optical distortion and striae can be prevented more reliably. can do.

In the method for producing a plastic lens of the present invention, the temperature change of the polymerizable composition between the start and end of the cooling step is preferably 5 ° C. or more and 50 ° C. or less.
According to such a configuration, the temperature of the polymerizable composition can be appropriately reduced by the cooling step, and the occurrence of optical distortion and striae can be prevented while suppressing an increase in production time.

Here, if the temperature change is less than 5 ° C., the effect of suppressing a local increase in the polymerization rate is small, such being undesirable. On the other hand, if the temperature change exceeds 50 ° C., the polymerization rate is too low and the time required for the production of the plastic lens increases, which is not preferable. Further, since the temperature difference is large, there is a problem that the shrinkage amount of the molding mold increases, and the target center thickness and desired frequency cannot be obtained.
The temperature change is more preferably 10 ° C. or higher and 45 ° C. or lower, and further preferably 10 ° C. or higher and 40 ° C. or lower.

In the plastic lens manufacturing method of the present invention, the initial temperature is preferably 0 ° C. or higher and 50 ° C. or lower.
According to such a configuration, by setting the initial temperature within an appropriate range, the polymerizable composition has a viscosity that is easy to handle and the filling process is facilitated, and unevenness during filling is less likely to occur. In addition, the polymerization rate in the holding step is moderately maintained, and the effect of shortening the production time can be obtained.

Here, when the initial temperature is less than 0 ° C., the viscosity of the polymerizable composition becomes high, the filling process becomes difficult, the polymerization rate is lowered, and the effect of shortening the production time is reduced. On the other hand, if the initial temperature exceeds 50 ° C., there is a risk of leakage of the polymerizable composition due to the thermal expansion of the molding mold and the generation of bubbles, and the polymerization rate in the holding step is too high, resulting in a local polymerization rate. It is not preferable because the rise tends to occur.
The initial temperature is more preferably 5 ° C. or more and 45 ° C. or less, and further preferably 10 ° C. or more and 40 ° C. or less.

In the method for producing a plastic lens of the present invention, it is preferable that in the holding step, the polymerizable composition is maintained at the initial temperature.
According to such a configuration, by maintaining the polymerizable composition at the initial temperature, expansion and contraction of the molding mold can be prevented, and problems such as leakage of the polymerizable composition can be prevented.

In the method for producing a plastic lens of the present invention, it is preferable that the holding step includes an initial heating step of heating the polymerizable composition.
According to such a configuration, since the temperature of the polymerizable composition is increased in the initial heating step, the polymerization rate can be increased, and the time required for manufacturing the plastic lens can be shortened.

In the method for producing a plastic lens of the present invention, in the initial heating step, the polymerizable composition is preferably heated at a temperature rising speed of 0.1 ° C./hour or more and 3.0 ° C./hour or less.
According to such a configuration, the time required for producing the plastic lens can be shortened by increasing the polymerization rate without causing problems such as leakage of the polymerizable composition.

Here, it is not preferable that the temperature increase rate is less than 0.1 ° C./hour because the temperature increase is too slow and the effect of shortening the production time is small. On the other hand, when the temperature rising speed exceeds 3.0 ° C./hour, there is a risk of problems such as leakage of the polymerizable composition due to thermal expansion of the molding mold, and the polymerization rate in the initial heating step is too high. This is not preferable because a local increase in polymerization rate is likely to occur.
The temperature rising speed is more preferably 0.5 ° C./hour or more and 2.5 ° C./hour or less, and further preferably 1 ° C./hour or more and 2 ° C./hour or less.

In the method for producing a plastic lens of the present invention, the curing step includes a heating step of heating the polymerizable composition to 80 ° C. or higher and 200 ° C. or lower after the polymerizable composition is gelled, and after the heating step, And a high temperature maintaining step of maintaining the temperature of the heated polymerizable composition for 5 minutes or more.
According to such a configuration, after the gelation is completed and there is no possibility of occurrence of optical distortion or striae, the polymerizable composition is fully cured to obtain a finished plastic lens.

Here, when the heating temperature in the heating step is less than 80 ° C. or the high temperature maintaining step is less than 5 minutes, the main curing cannot be sufficiently performed, which is not preferable. On the other hand, when the heating temperature exceeds 200 ° C., the plastic lens may be discolored or deformed, and the molding mold may be damaged.
In addition, as for heating temperature, it is more preferable that they are 100 degreeC or more and 150 degrees C or less.
Moreover, it is preferable to implement a heating process over the time of 5 minutes or more and 50 hours or less, and it is more preferable to take the time of 1 hour or more and 25 hours or less. Less than 5 minutes is not preferable because the polymerizable composition is not completely cured. If it exceeds 50 hours, the plastic lens may be discolored or deformed, and the molding mold may be damaged, and at the same time, the manufacturing time is increased, which is not preferable.
The high temperature maintaining step is preferably 10 hours or less from the viewpoint of production time, and more preferably 30 minutes or more and 5 hours or less.

In the method for producing a plastic lens of the present invention, the polymerizable composition preferably contains a compound having a thioepoxy group or an epoxy group.
In the plastic lens of the present invention, the polymerizable composition preferably contains at least one of a polyisocyanate compound and a polyisothiocyanate compound and at least one of a polyol compound and a polythiol compound.
Moreover, in the manufacturing method of the plastic lens of this invention, it is preferable that the said polymeric composition contains the compound which has at least any one of an acryl group, a methacryl group, and an allyl group.
In the method for producing a plastic lens of the present invention, the polymerizable composition comprises (A) an inorganic compound having a sulfur atom and / or selenium atom, and (B) a structure represented by the following general formula (1): It is preferable to contain the compound which has 1 or more in 1 molecule, and (C) SH group containing organic compound which has 1 or more of SH groups in 1 molecule.

In the formula, R ¹ is a hydrocarbon having 1 to 10 carbon atoms, R ² , R ³ and R ⁴ are each a hydrocarbon group or hydrogen having 1 to 10 carbon atoms, Y is O, S, Se or Te, l = 0 -5, m = 0 or 1, n = 1-5.

  When these polymerizable compositions are polymerized and cured, a resin having a high refractive index can be obtained, so that a thick plastic lens having a high refractive index can be obtained without optical distortion or striae.

  ADVANTAGE OF THE INVENTION According to this invention, the manufacturing method of the plastic lens which has practical productivity and can obtain a thick plastic lens without an optical distortion, a striae, etc. can be provided.

Hereinafter, embodiments of the plastic lens manufacturing method of the present invention will be described in detail. In this embodiment, a plastic lens for spectacles is exemplified, but the use of the plastic lens of the present invention is not limited to this, and can be preferably applied to various optical lenses including a camera lens, for example.
The plastic lens manufactured in this embodiment is thicker than a general plastic lens, and has a thickness of about 10 mm to 15 mm, for example.

  The method for producing a plastic lens according to the present embodiment includes a filling step of filling a polymerizable mold with a polymerizable composition, and a curing step of curing the polymerizable composition by exposing the molding mold under a predetermined temperature condition. .

[Filling process]
In the filling step, the polymerizable composition is filled into the molding mold.
As the molding mold, for example, a glass mold in which two glass molds corresponding to the convex surface side and the concave surface side of the lens are arranged to face each other and the peripheral surface thereof is wound with a gasket or an adhesive tape and sealed can be used.

The temperature of the polymerizable composition in the filling step can be arbitrarily set, and this temperature is set as an initial temperature that serves as a reference for the holding step described later.
For adjusting the temperature of the molding mold and the polymerizable composition, for example, an apparatus such as an electric furnace can be appropriately used.

The initial temperature is preferably 0 ° C. or higher and 50 ° C. or lower.
If the initial temperature is 0 ° C. or higher, the filling step can be easily performed by lowering the viscosity of the polymerizable composition, and the effect of shortening the production time can be obtained by securing the polymerization rate in the holding step. . In addition, if the initial temperature is 50 ° C. or less, leakage of the polymerizable composition and generation of bubbles due to thermal expansion of the molding mold can be prevented, and uneven polymerization rate occurs due to an increase in the polymerization rate in the holding step. Can be prevented.

[Curing process]
The curing process includes a holding process, a cooling process, a low temperature maintaining process, a heating process, and a high temperature maintaining process.

[Holding process]
The holding step is a step of keeping the polymerizable composition at an initial temperature or higher from the filling step to the cooling step.
In the present embodiment, the holding step includes an initial heating step for heating the polymerizable composition.
In the initial heating step, the polymerizable composition is heated at a temperature rising speed of 0.1 ° C./hour or more and 3.0 ° C./hour or less.
If the heating rate is less than 0.1 ° C./hour, the effect of increasing the polymerization rate and shortening the production time can be obtained. If the heating rate is 3.0 ° C./hour or less, problems such as leakage of the polymerizable composition due to thermal expansion of the molding mold can be prevented.

[Cooling process]
The cooling step is a step of cooling the polymerizable composition by a predetermined temperature after a predetermined time has elapsed since the start of the holding step.

When the time from the start of the curing process (that is, the end of the filling process) to the end is 100%, the cooling process may be performed at the time when the time of 15% or more and 80% or less has elapsed from the start of the holding process. preferable.
If the cooling process is performed at a time of 15% or more from the start of the holding process, the maintenance process time is secured to some extent, and the effect of shortening the manufacturing time can be obtained. If it is 80% or less, a cooling process can be implemented before gelatinization of a polymeric composition, and an optical distortion, a striae, etc. can be prevented.

The temperature change of the polymerizable composition between the start and end of the cooling step is preferably 5 ° C. or more and 50 ° C. or less.
If the temperature change is 5 ° C. or more, an effect of suppressing a local increase in the polymerization rate can be obtained. If a temperature change is 50 degrees C or less, it can prevent that a polymerization rate falls too much and manufacturing time increases excessively. Moreover, shrinkage | contraction of the shaping | molding mold by a temperature difference can be suppressed, and the target center thickness and desired frequency can be obtained.

[Low temperature maintenance process]
The low temperature maintaining step is a step of maintaining the temperature of the cooled polymerizable composition for a predetermined time after the cooling step.
The low temperature maintaining step is preferably performed up to a time region where the polymerizable composition is sufficiently gelled and no optical distortion or striae occurs.

[Heating process and high temperature maintenance process]
The heating step is a step of heating the polymerizable composition to 80 ° C. or higher and 200 ° C. or lower after the polymerizable composition is gelled.
The high temperature maintaining step is a step of maintaining the temperature of the heated polymerizable composition for 5 minutes or more after the heating step.
These are processes for completely curing the polymerizable composition and completing a plastic lens.
If the heating temperature in the heating step is 80 ° C. or higher and the high temperature maintaining step is 5 minutes or longer, the polymerizable composition can be fully cured. If heating temperature is 200 degrees C or less, it can prevent damaging a plastic lens and a shaping | molding mold by high temperature.

[About post-processing]
The polymerization curing of the polymerizable composition is completed up to the high temperature maintaining step, and the plastic lens is completed.
Thereafter, the plastic lens is gradually cooled to a temperature at which it can be taken out, for example, up to 80 ° C. or less, more preferably 60 ° C. or less over 0.1 to 50 hours, and more preferably over 1 to 25 hours.
This plastic lens can be used as a spectacle lens or the like as it is, but a functional layer such as a primer layer, a hard coat layer, an antireflection layer or an antifouling layer may be formed on the surface. As these functional layers, conventionally known layers can be appropriately selected.

[Polymerizable composition]
Hereinafter, the polymerizable composition used in the present embodiment will be described.
The polymerizable composition is not particularly limited as long as it is a composition that is polymerized and cured by heat. For example, the following can be used.
In addition, the composition enumerated below is an example of the composition which can be utilized as a polymerizable composition, Comprising: The polymerizable composition of this invention is not limited to these compositions at all.

[Composition containing a compound having a thioepoxy group or the like]
A composition containing a thioepoxy group or a compound having an epoxy group can be suitably used as the polymerizable composition.
As the compound having a thioepoxy group, a known compound having a thioepoxy group can be used. Specific examples of the compound having a thioepoxy group include a thioepoxy compound obtained by replacing part or all of the oxygen of an epoxy group of an existing epoxy compound with sulfur. Further, in order to increase the refractive index of the plastic lens, a compound containing a sulfur atom in addition to the thioepoxy group is more preferable.

Specific examples include 1,2-bis (β-epithiopropylthio) ethane, bis (β-epithiopropyl) sulfide, 1,4-bis (β-epithiopropylthiomethyl) benzene, 2,5- Examples thereof include bis (β-epithiopropylthiomethyl) -1,4-dithiane and bis (2,3-epithiopropyl) disulfide.
In addition, 1,2-bis (2,3-epithiopropylthio) ethane, 1,2-bis (2,3-epithiopropylthio) propane, 1,3-bis (2,3-epithiopropylthio) ) Propane, 1,4-bis (2,3-epithiopropylthio) butane, 2,2-bis (2,3-epithiopropylthio) -1,3-bis (2,3-epithiopropylthio) A chain aliphatic 2,3-epithiopropylthio compound such as methyl) propane, 1,3-bis (2,3-epithiopropylthio) cyclohexane, 1,4-bis (2,3-epi) Cycloaliphatic 2,3-epithiopropylthio compounds such as thiopropylthio) cyclohexane and 2,5-bis (2,3-epithiopropylthiomethyl) -1,4-dithiane, bis (2,3- Epithiopropyl) disulfide, , 2-bis (2,3-epithiopropylthio) benzene, 1,3-bis (2,3-epithiopropylthio) benzene, bis (2,3-epithiopropyldithio) methane, bis (2, 3-epithiopropyldithio) ethane, bis (6,7-epithio-3,4-dithiaheptane) sulfide, 1,4-dithian-2,5-bis (2,3-epithiopropyldithiomethyl), 1, In addition to a thioepoxy group such as 3-bis (2,3-epithiopropyldithiomethyl) benzene, a compound containing a sulfur atom may be mentioned.

As the compound having an epoxy group, a known compound having an epoxy group can be used. Specific examples of compounds having at least one epoxy group in one molecule include, for example, phenol-derived epoxy compounds, alcohol-derived epoxy compounds, carboxylic acid-derived epoxy compounds, amine-derived epoxy compounds, diphenyl epoxy resins, and ethylene oxide. , Propylene oxide, and a polymer having an epoxy group.
Examples of the epoxy compound derived from phenol include a compound obtained by reacting a phenol compound such as resorcinol, hydroquinone, bisphenol A, and bisphenol F with epichlorohydrin, or a commercially available product Epicoat 828 manufactured by Yuka Shell Epoxy. .
Examples of alcohol-derived epoxy compounds include ethanol, propanol, butanol, octanol, ethylene glycol, diethylene glycol, polyethylene glycol, propylene glycol, tripropylene glycol, polypropylene glycol, glycerin, trimethylolpropane, pentaerythritol, sorbitol, and 2,4-diethyl. Examples include epoxy compounds obtained by reacting alcohols such as -1,5-pentanediol and epichlorohydrin.

Examples of the epoxy compound derived from carboxylic acid include epoxy compounds obtained by reacting acetic acid, propionic acid, butyric acid, stearic acid, phthalic acid and the like with epichlorohydrin.
Examples of the amine-derived epoxy compounds include epoxy compounds obtained by reacting epichlorohydrin with diaminodiphenylmethane, p-aminomethylphenol, pheylylenediamine, and the like.
As an actual example including the above-mentioned epoxy compound, as a compound containing one epoxy group in one molecule, 2-ethylhexyl glycidyl ether, phenyl glycidyl ether, allyl glycidyl ether, pt-butylphenyl glycidyl ether Etc. Examples of the compound having two or more epoxy groups in one molecule include 1,6-hexanediol diglycol ether, hydroquinone diglycol ether, terephthalic acid diglycol ether, or ethylene or propylene having n = 1 to 22 repeating units. Examples include glycol diglycidyl ether, trimethylolpropane triglycidyl ether, pentaerythritol tetraglycidyl ether, sorbitol polyglycidyl ether, and bis (2,3-epoxypropyl) disulfide.

  The polymerizable composition contains such a thioepoxy group or a compound having an epoxy group as a main component. As content with respect to the polymeric composition of these compounds, it is preferable that they are 50 to 99 mass%.

[Composition containing polyisocyanate compound and polyol compound, etc.]
A composition containing at least one of a polyisocyanate compound and a polyisothiocyanate compound and at least one of a polyol compound and a polythiol compound can be suitably used as the polymerizable composition.
As the polyisocyanate compound or polyisothiocyanate compound, compounds having a known isocyanate group or isothiocyanate group can be used. Suitable examples are m-xylylene diisocyanate and norbornane diisocyanate, and one or both may be used.

  Specific examples of the polyisocyanate compound include 1,2-diisocyanatobenzene, 1,3-diisocyanatobenzene, 1,4-diisocyanatobenzene, 2,4-diisocyanatotoluene, ethylphenylene diisocyanate. , Isopropylphenylene diisocyanate, dimethylphenylene diisocyanate, diethylphenylene diisocyanate, diisopropylphenylene diisocyanate, trimethylbenzene triisocyanate, benzene triisocyanate, biphenyl diisocyanate, toluidine diisocyanate, 4,4'-methylenebis (phenylisocyanate), 4,4'- Methylenebis (2-methylphenylisocyanate), bibenzyl-4,4′-diisocyanate, bis (isocyanatophenyl) ethylene Isophorone diisocyanate, cyclohexane diisocyanate, methylcyclohexane diisocyanate, 4,4′-methylenebis (cyclohexyl isocyanate), 4,4′-methylenebis (2-methylcyclohexylisocyanate), 3,8-bis (isocyanatomethyl) tricyclodecane, 3 , 9-bis (isocyanatomethyl) tricyclodecane, 4,8-bis (isocyanatomethyl) tricyclodecane, 4,9-bis (isocyanatomethyl) tricyclodecane.

Further, p-xylylene diisocyanate, tetrachloro-m-xylylene diisocyanate, hydrogenated xylylene diisocyanate, hydrogenated diphenylmethane diisocyanate, tetramethylxylylene diisocyanate, 2,5-bis (isocyanate methyl) bicyclo [2.2.1]. ] Heptane, 2,6-bis (isocyanatomethyl) bicyclo [2.2.1] heptane, 3,8-bis (isocyanatomethyl) tricyclo [5.2.1,02,6] -decane, 3,9- Bis (isocyanatomethyl) tricyclo [5.2.1.02,6] -decane, 4,8-bis (isocyanatomethyl) tricyclo [5.2.1,02,6] -decane, 4,9-bis ( Isocyanatomethyl) tricyclo [5.2.1,02,6] -decane, dimer acid diiso Polyisocyanate compounds such as ananate and allophanate-modified products of these compounds, 1,3-bis (α, α-dimethylisocyanatomethyl) benzene, 1,4-bis (α, α-dimethylisocyanatomethyl) benzene, hexamethylene diisocyanate , Isophorone diisocyanate, tolylene diisocyanate, diphenylmethane diisocyanate, polymeric diphenylmethane diisocyanate, tolidine diisocyanate, naphthalene diisocyanate, 4,4'-diphenylmethane diisocyanate, hexamethylene diisocyanate biuretation reaction product, hexamethylene diisocyanate and trimethylolpropane adduct product 4,4'-dicyclohexylmethane diisocyanate, modified isocyanurate, etc. It is.
In addition, although illustrated with isocyanate, isothiocyanate may be sufficient.
These polyisocyanate compounds and polyisothiocyanate compounds can be used alone or in admixture of two or more.

  Examples of the polyol compound include ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, butylene glycol, neopentyl glycol, glycerin, trimethylolethane, trimethylolpropane, butanetriol, 1,2-methylglucoside, pentaerythritol, Dipentaerythritol, tripentaerythritol, sorbitol, erythritol, threitol, ribitol, arabinitol, xylitol, allitol, mannitol, dolcitol, idiitol, glycol, inositol, hexanetriol, triglycerol, diglycerol, triethylene glycol, polyethylene glycol, tris (2 -Hydroxyethyl) isocyanurate, cyclobuta Diol, cyclopentanediol, cyclohexanediol, cycloheptanediol, cyclooctanediol, cyclohexanedimethanol, hydroxypropylcyclohexanol, tricyclo [5,2,1,0,2,6] decane-dimethanol, bicyclo [4,3 , 0] -nonanediol, dicyclohexanediol, tricyclo [5,3,1,1] dodecanediol, bicyclo [4,3,0] nonanedimethanol, tricyclo [5,3,1,1] dodecane-diethanol, Aliphatic acids such as hydroxypropyltricyclo [5,3,1,1] dodecanol, spiro [3,4] octanediol, butylcyclohexanediol, 1,1'-bicyclohexylidenediol, cyclohexanetriol, maltitol, lactitol Po All, dihydroxynaphthalene, trihydroxynaphthalene, tetrahydroxynaphthalene, dihydroxybenzene, benzenetriol, biphenyltetraol, pyrogallol, (hydroxynaphthyl) pyrogallol, trihydroxyphenanthrene, bisphenol A, bisphenol F, xylylene glycol, tetrabromobisphenol A, etc. Aromatic polyols, di- (2-hydroxyethyl) sulfide, 1,2-bis- (2-hydroxyethyl mercapto) ethane, bis (2-hydroxyethyl) disulfide, 1,4-dithian-2,5-diol Bis (2,3-dihydroxypropyl) sulfide, tetrakis (4-hydroxy-2-thiabutyl) methane, bis (4-hydroxyphenyl) sulfone (trade name Enol S), tetrabromobisphenol S, tetramethylbisphenol S, 4,4′-thiobis (6-tert-butyl-3-methylphenol), 1,3-bis (2-hydroxyethylthioethyl) -cyclohexane, etc. Examples include polyols containing sulfur atoms.

  Examples of the polythiol compound include various compounds shown below and those employing one or more of these compounds. Suitable examples are 1,1,3,3-tetrakis (mercaptomethylthio) propane and 1,1,2,2-tetrakis (mercaptomethylthio) ethane, one or both may be used. Examples of other polythiol compounds include the following. 1,2,5-trimercapto-4-thiapentane, 3,3-dimercaptomethyl-1,5-dimercapto-2,4-dithiapentane, 3-mercaptomethyl-1,5-dimercapto-2,4-dithiapentane, 3-mercaptomethylthio-1,7-dimercapto-2,6-dithiaheptane, 3,6-dimercaptomethyl-1,9-dimercapto-2,5,8-trithianonane, 3,7-dimercaptomethyl-1,9 -Dimercapto-2,5,8-trithianonane, 4,6-dimercaptomethyl-1,9-dimercapto-2,5,8-trithianonane, 3-mercaptomethyl-1,6-dimercapto-2,5-dithiahexane, 3-mercaptomethylthio-1,5-dimercapto-2-thiapentane, 1,1,2,2-tetrakis (mercapto Tilthio) ethane, 1,4,8,11-tetramercapto-2,6,10-trithiaundecane, 1,4,9,12-tetramercapto-2,6,7,11-tetrathiadecane, 2, 3-dithia-1,4-butanedithiol, 2,3,5,6-tetrathia-1,7-heptanedithiol, 2,3,5,6,8,9-hexathia-1,10-decanedithiol, 4 , 5-bis (mercaptomethylthio) -1,3-dithiolane, 4,6-bis (mercaptomethylthio) -1,3-dithiane, 2-bis (mercaptomethylthio) methyl-1,3-dithietane, 2- (2, 2-bis (mercaptomethylthio) ethyl) -1,3-dithietane and the like.

  Also, 3-mercapto-1,2-propanediol, glycerin di (mercaptoacetate), 1-hydroxy-4-mercaptocyclohexane, 2,4-dimercaptophenol, 2-mercaptohydroquinone, 4-mercaptophenol, 3,4 Dimercapto-2-propanol, 1,3-dimercapto-2-propanol, 2,3-dimercapto-1-propanol, 1,2-dimercapto-1,3-butanediol, pentaerythritol tris (3-mercaptopropionate ), Pentaerythritol mono (3-mercaptopropionate), pentaerythritol bis (3-mercaptopropionate), pentaerythritol tris (thioglycolate), dipentaerythritol pentakis (3-mercaptopropio) Over G), hydroxymethyl - tris (mercaptoethylthiomethyl) methane, 1-hydroxyethylthio-3-mercaptoethylthio benzene.

  Furthermore, as a compound having two or more mercapto groups in the structure, methanedithiol, 1,2-ethanedithiol, 1,1-propanedithiol, 1,2-propanedithiol, 1,3-propanedithiol, 2,2 -Propanedithiol, 1,6-hexanedithiol, 1,2,3-propanetrithiol, 1,1-cyclohexanedithiol, 1,2-cyclohexanedithiol, 2,2-dimethylpropane-1,3-dithiol, 3, 4-dimethoxybutane-1,2-dithiol, 2-methylcyclohexane-2,3-dithiol, 1,1-bis (mercaptomethyl) cyclohexane, bis (2-mercaptoethyl ester) thiomalate, 2,3-dimercapto- 1-propanol (2-mercaptoacetate), 2,3-dimerca To-1-propanol (3-mercaptopropionate), diethylene glycol bis (2-mercaptoacetate), diethylene glycol bis (3-mercaptopropionate), 1,2-dimercaptopropyl methyl ether, 2,3-dimercapto Propyl methyl ether, 2,2-bis (mercaptomethyl) -1,3-propanedithiol, bis (2-mercaptoethyl) ether, ethylene glycol bis (2-mercaptoacetate), ethylene glycol bis (3-mercaptopropionate) ), Trimethylolpropane bis (2-mercaptoacetate), trimethylolpropane bis (3-mercaptopropionate), pentaerythritol tetrakis (2-mercaptoacetate), pentaerythritol tetra (3-mercaptopropionate), aliphatic polythiol compounds such as tetrakis (mercaptomethyl) methane, 1,2-dimercaptobenzene, 1,3-dimercaptobenzene, 1,4-dimercaptobenzene, 1,2 -Bis (mercaptomethyl) benzene, 1,3-bis (mercaptomethyl) benzene, 1,4-bis (mercaptomethyl) benzene, 1,2-bis (mercaptoethyl) benzene, 1,3-bis (mercaptoethyl) Benzene, 1,4-bis (mercaptoethyl) benzene, 1,2,3-trimercaptobenzene, 1,2,4-trimercaptobenzene, 1,3,5-trimercaptobenzene, 1,2,3-tris (Mercaptomethyl) benzene, 1,2,4-tris (mercaptomethyl) benzene, 1,3,5-tris (Mercaptomethyl) benzene, 1,2,3-tris (mercaptoethyl) benzene, 1,2,4-tris (mercaptoethyl) benzene, 1,3,5-tris (mercaptoethyl) benzene, 2,5-toluene Dithiol, 3,4-toluenedithiol, 1,3-di (p-methoxyphenyl) propane-2,2-dithiol, 1,3-diphenylpropane-2,2-dithiol, phenylmethane-1,1-dithiol, Aromatic polythiols such as 2,4-di (p-mercaptophenyl) pentane, 1,2-bis (mercaptoethylthio) benzene, 1,3-bis (mercaptoethylthio) benzene, 1,4-bis (mercaptoethyl) Thio) benzene, 1,2,3-tris (mercaptomethylthio) benzene, 1,2,4-tris (mercapto) Tilthio) benzene, 1,3,5-tris (mercaptomethylthio) benzene, 1,2,3-tris (mercaptoethylthio) benzene, 1,2,4-tris (mercaptoethylthio) benzene, 1,3,5 -Aromatic polythiol compounds containing sulfur atoms in addition to mercapto groups such as tris (mercaptoethylthio) benzene, etc., and their nuclear alkylated products, bis (mercaptomethyl) sulfide, bis (mercaptomethyl) disulfide, bis (mercaptoethyl) ) Sulfide, bis (mercaptoethyl) disulfide, bis (mercaptopropyl) sulfide, bis (mercaptomethylthio) methane, bis (2-mercaptoethylthio) methane, bis (3-mercaptopropylthio) methane, 1,2-bis ( Mercaptomethylthio) Tan, 1,2-bis (2-mercaptoethylthio) ethane, 1,2-bis (3-mercaptopropyl) ethane, 1,3-bis (mercaptomethylthio) propane, 1,3-bis (2-mercaptoethyl) Thio) propane, 1,3-bis (3-mercaptopropylthio) propane, 1,2,3-tris (mercaptomethylthio) propane, 1,2,3-tris (2-mercaptoethylthio) propane, 1,2 , 3-tris (3-mercaptopropylthio) propane, 1,2-bis [(2-mercaptoethyl) thio] -3-mercaptopropane, 4-mercaptomethyl-3,6-dithia-1,8-octanedithiol 4,8-dimercaptomethyl-1,11-mercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,1 1-mercapto-3,6,9-trithiaundecane, 5,7-dimercaptomethyl-1,11-mercapto-3,6,9-trithiaundecane, tetrakis (mercaptomethylthiomethyl) methane, tetrakis (2- Mercaptoethylthiomethyl) methane, tetrakis (3-mercaptopropylthiomethyl) methane, bis (2,3-dimercaptopropyl) sulfide, bis (1,3-dimercaptopropyl) sulfide, 2,5-dimercapto-1, 4-dithiane, 2,5-dimercaptomethyl-1,4-dithiane, 2,5-dimercaptomethyl-2,5-dimethyl-1,4-dithiane, bis (mercaptomethyl) disulfide, bis (mercaptoethyl) Disulfides, bis (mercaptopropyl) disulfides, etc., and their thiols Esters of richolic acid and mercaptopropionic acid, hydroxymethyl sulfide bis (2-mercaptoacetate), hydroxymethyl sulfide bis (3-mercaptopropionate), hydroxyethyl sulfide bis (2-mercaptoacetate), hydroxyethyl sulfide bis (3 -Mercaptopropionate), hydroxypropyl sulfide bis (2-mercaptoacetate), hydroxypropyl sulfide bis (3-mercaptopropionate), hydroxymethyl disulfide bis (2-mercaptoacetate), hydroxymethyl disulfide bis (3-mercapto Propionate), hydroxyethyl disulfide bis (2-mercaptoacetate), hydroxyethyl disulfide bis (3-mercapto) Lopionate), hydroxypropyl disulfide bis (2-mercaptoacetate), hydroxypropyl disulfide bis (3-mercaptopropionate), 2-mercaptoethyl ether bis (2-mercaptoacetate), 2-mercaptoethyl ether bis (3-mercapto) Propionate), 1,4-dithian-2,5-diol bis (2-mercaptoacetate), 1,4-dithian-2,5-diol bis (3-mercaptopropionate), bis (thiodiglycolate) (2 -Mercaptoethyl ester), thiodipropionic acid bis (2-mercaptoethyl ester), 4,4-thiodibutyric acid bis (2-mercaptoethyl ester), dithiodiglycolic acid bis (2-mercaptoethyl ester), dithiodipropion acid Bis (2-mercaptoethyl ester), 4,4-dithiodibutyric acid bis (2-mercaptoethyl ester), thiodiglycolic acid bis (2,3-dimercaptopropyl ester), thiodipropionic acid bis (2,3 -Dimercaptopropyl ester), dithioglycolic acid bis (2,3-dimercaptopropyl ester), dithiodipropionic acid bis (2,3-dimercaptopropyl ester) and other aliphatic compounds containing sulfur atoms in addition to mercapto groups Examples include polythiol compounds.

  The polymerizable composition contains these compounds as main components. The total content of these compounds is preferably 90% by mass or more and 99.9% by mass or less.

[Composition containing a compound capable of radical polymerization]
Further, a composition containing a radical polymerizable compound containing at least one unsaturated hydrocarbon group such as vinyl group, allyl group, acrylic group or methacryl group, vinylidene group, vinylene group or the like as a radical polymerizable group in the molecule. Can be suitably used as a polymerizable composition.
Among these, a compound having an acryl group or a methacryl group, or a compound having an allyl group is preferably used from the viewpoint of optical characteristics, mechanical characteristics, heat resistance, and the like of the lens.

  Specific examples of the compound having an acrylic group or a methacrylic group include acrylic acid, methyl acrylate, ethyl acrylate, n-butyl acrylate, butoxyethyl acrylate, benzyl acrylate, phenyl acrylate, phenoxyethyl acrylate, and cyclohexyl acrylate. , Dicyclopentanyl acrylate, dicyclopentenyl acrylate, dicyclopentenyloxyethyl acrylate, tetrahydrofurfuryl acrylate, isobornyl acrylate, 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, 2-acryloyloxyethyl succinic acid, Monofunctional acrylic esters such as 2-acryloyloxyethyl phthalic acid, caprolactone acrylate, glycidyl acrylate, methacrylic acid, meta Methyl acrylate, ethyl methacrylate, n-butyl methacrylate, 2-ethylhexyl methacrylate, butoxymethyl methacrylate, benzyl methacrylate, phenyl methacrylate, phenoxyethyl methacrylate, cyclohexyl methacrylate, dicyclopentanyl methacrylate, dicyclopentenyl methacrylate, Dicyclopentenyloxyethyl methacrylate, tetrahydrofurfuryl methacrylate, isobornyl methacrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl methacrylate, 2-hydroxybutyl methacrylate, glycerol methacrylate, 2-methacryloyloxyethyl succinic acid, 2-methacryloyl Oxyethylphthalic acid, caprolactone methacrylate, glycidylme Such as a monofunctional methacrylic acid esters such as acrylate and the like.

  Furthermore, in order to increase the degree of crosslinking of these, ethylene glycol diacrylate, diethylene glycol diacrylate, triethylene glycol diacrylate, tetraethylene glycol diacrylate, polyethylene glycol diacrylate, allyl acrylate, bis (acryloxyethyl) hydroxyethyl isocyanurate Bis (acryloxy neopentyl glycol) adipate, 1,3-butylene glycol diacrylate, 1,6-hexanediol diacrylate, neopentyl glycol diacrylate, propylene glycol diacrylate, polypropylene glycol diacrylate, 2-hydroxy-1 , 3-Diacryloxypropane, 2,2-bis [4- (acryloxy) phenyl] propane, 2,2-bi [4- (acryloxyethoxy) phenyl] propane, 2,2-bis [4- (acryloxyethoxy diethoxy) phenyl] propane, 2,2-bis [4- (acryloxyethoxy polyethoxy) phenyl] propane, Hydroxypivalate neopentyl glycol diacrylate, 1,4-butanediol diacrylate, dicyclopentanyl diacrylate, dipentaerythritol hexaacrylate, dipentaerythritol monohydroxypentaacrylate, ditrimethylolpropane tetraacrylate, pentaerythritol triacrylate, Tetrabromobisphenol A diacrylate, triglycerol diacrylate, trimethylolpropane triacrylate, tris (acryloxyethyl) isocyanur , Ethylene glycol dimethacrylate, diethylene glycol dimethacrylate, triethylene glycol dimethacrylate, tetraethylene glycol dimethacrylate, polyethylene glycol dimethacrylate, propylene glycol dimethacrylate, polypropylene glycol dimethacrylate, 1,3-butylene glycol dimethacrylate, 1, 4-butanediol dimethacrylate, 1,6-hexanediol dimethacrylate, neopentyl glycol dimethacrylate, 2-hydroxy-1,3-dimethacryloxypropane, 2,2-bis [4- (methacryloxy) phenyl] propane, 2,2-bis [4- (methacryloxyethoxy) phenyl] propane, 2,2-bis [4- (methacryloxyethoxy die) Toxi) phenyl] propane, 2,2-bis [4- (methacryloxyethoxy polyethoxy) phenyl] propane, tetrabromobisphenol A dimethacrylate, dicyclopentanyl dimethacrylate, dipentaerythritol hexamethacrylate, glycerol dimethacrylate, hydroxy Pivalic acid neopentyl glycol dimethacrylate, dipentaerythritol monohydroxypentamethacrylate, ditrimethylolpropane tetramethacrylate, pentaerythritol trimethacrylate, pentaerythritol tetramethacrylate, triglycerol dimethacrylate, trimethylolpropane trimethacrylate, tris (methacryloxyethyl) Polyfunctional monomers such as isocyanurate can also be used .

As the compound having an allyl group, a known compound having an allyl group can be used. Specific examples include allyl compounds such as allylbenzene, allyl-3-cyclohexanepropionate, 1-allyl-3,4-dimethoxybenzene, allylphenoxyacetate, allylphenylacetate, allylcyclohexane, and allyl polycarboxylate. It is done.
Furthermore, in order to increase the degree of crosslinking, polyfunctional monomers such as diallyl phthalate, diallyl terephthalate, diallyl isophthalate, and diethylene glycol bisallyl carbonate can also be used.

  Among the compounds having a vinyl group, as a sulfur-containing vinyl compound having one or more polymerizable double bonds in the molecule, for example, 2- (4-vinylbenzylthio) ethanol and m-xylylene diisocyanate are urethanized. Sulfur-containing vinyl compound obtained by urethanization, sulfur-containing vinyl compound obtained by urethanization of 2- (3-vinylbenzylthio) ethanol and m-xylylene diisocyanate, p-bis (β-methacryloyloxyethylthio) xylylene, etc. Is mentioned.

  The polymerizable composition contains these compounds as main components. The total content of these compounds is preferably 50% by mass or more and 99.9% by mass or less.

[Composition containing an inorganic compound having a sulfur atom or a selenium atom]
(A) an inorganic compound having a sulfur atom and / or selenium atom, (B) a compound having one or more structures represented by the following general formula (1) in one molecule, and (C) in one molecule A composition containing an SH group-containing organic compound having one or more SH groups can be suitably used as the polymerizable composition.

In the formula, R ¹ is a hydrocarbon having 1 to 10 carbon atoms, R ² , R ³ and R ⁴ are each a hydrocarbon group or hydrogen having 1 to 10 carbon atoms, Y is O, S, Se or Te, l = 0 -5, m = 0 or 1, n = 1-5.

The inorganic compound (A) used in the present invention is all inorganic compounds having at least one of a sulfur atom and a selenium atom.
As for the addition amount of the inorganic compound (A), when the total of the inorganic compound (A) and the compound (B) is 100% by mass, 1% by mass to 50% by mass is used, but 1% by mass to 30% by mass. The following is preferable, and more preferably 5% by mass or more and 20% by mass or less.

  Specific examples of the inorganic compound (A) having a sulfur atom include sulfur, hydrogen sulfide, carbon disulfide, carbon selenosulfide, ammonium sulfide, sulfur dioxide, sulfur trioxide, and other sulfur oxides, thiocarbonate, sulfuric acid, and the like. Salt, hydrogen sulfate, sulfite, hyposulfite, persulfate, thiocyanate, thiosulfate, sulfur dichloride, thionyl chloride, thiophosgene and other halides, boron sulfide, nitrogen sulfide, silicon sulfide, phosphorus sulfide, Examples thereof include arsenic sulfide, selenium sulfide, metal sulfide, and metal hydrosulfide. Among these, sulfur, carbon disulfide, phosphorus sulfide, selenium sulfide, metal sulfide and metal hydrosulfide are preferable, sulfur, carbon disulfide and selenium sulfide are more preferable, and sulfur is particularly preferable. .

The inorganic compound (A) having a selenium atom includes all inorganic compounds satisfying this condition except for the selenocarbon sulfide and selenium sulfide mentioned as specific examples of the inorganic compound (A) containing a sulfur atom.
Specific examples include selenium oxides such as selenium, hydrogen selenide, selenium dioxide, carbon diselenide, ammonium selenide, selenium dioxide, selenic acid and salts thereof, selenite and salts thereof, hydrogen selenate salts, seleno Examples thereof include sulfuric acid and its salts, selenopyrosulfuric acid and its salts, halides such as selenium tetrabromide and selenium oxychloride, selenocyanate, boron selenide, phosphorus selenide, arsenic selenide, metal selenide and the like. Among these, preferred are selenium, carbon diselenide, phosphorus selenide, and metal selenide, and particularly preferred are selenium and carbon diselenide.
The inorganic compound (A) having at least one of these sulfur atoms and selenium atoms may be used alone or in combination of two or more.

The compound (B) is a compound represented by the formula (1).
Specific examples include bis (β-epithiopropyl) sulfide, bis (β-epithiopropyl) disulfide, bis (β-epithiopropyl) trisulfide, bis (β-epithiopropylthio) methane, 1,2 -Bis (β-epithiopropylthio) ethane, 1,3-bis (β-epithiopropylthio) propane, 1,2-bis (β-epithiopropylthio) propane, 1,4-bis (β- And episulfides such as epithiopropylthio) butane and bis (β-epithiopropylthioethyl) sulfide. Compound (B) may be used alone or in combination of two or more. Among them, preferred specific examples are bis (β-epithiopropyl) sulfide and / or bis (β-epithiopropyl) disulfide, and the most preferred specific example is bis (β-epithiopropyl) sulfide.

  The addition amount of the compound (B) is 25% by mass or more and 96% by mass or less, more preferably 50% by mass or more and 80% by mass when the total of the compound (A) and the compound (B) is 100% by mass. % Or less.

The compound (C) is a compound having one or more thiol (SH) groups.
Since the thiol (SH) group has active hydrogen, a low yellow plastic lens can be obtained by adding to the compound (A) and the compound (B). Further, from the viewpoint of obtaining a polymerizable composition having a low viscosity, the compound (C) is more preferably a compound having only one thiol (SH) group.
Of these compounds (C), the compound (C) having an aromatic ring is preferable in order to maintain the high refractive index of the plastic lens, and the molecular weight of the compound (C) is required in order to realize the low yellow color of the plastic lens. Is preferably less than 200, and the molecular weight of the compound (C) is preferably 100 or more from the viewpoint that the compound (C) is liquid or solid and has a weak odor and is easy to handle.

  Specific examples of the compound (C) include methyl mercaptan, ethyl mercaptan, n-propyl mercaptan, n-butyl mercaptan, n-hexyl mercaptan, n-octyl mercaptan, n-decyl mercaptan, n-dodecyl mercaptan, n-tetradecyl. Mercaptan, n-hexadecyl mercaptan, n-octadecyl mercaptan, i-propyl mercaptan, t-butyl mercaptan, t-nonyl mercaptan, t-dodecyl mercaptan, allyl mercaptan, 2-mercaptoethanol, 2- (2-mercaptoethylthio) Ethanol, 3-mercapto-1,2-propanediol, 2-mercapto-1,3-propanediol, mercaptoacetic acid, mercaptoglycolic acid, mercaptopropionic acid, methyl mercapto Licolate, methyl mercaptopropionate, (2-mercaptoethylthioacetic acid) methyl ester, (2-mercaptoethylthiopropionic acid) methyl ester, 2-dimethylaminoethanethiol, 2-diethylaminoethanethiol, 2-dibutylaminoethanethiol 2- (1-pyrrolidinyl) ethanethiol, 2- (1-piperidinyl) ethanethiol, 2- (4-morpholinyl) ethanethiol, 2- (N-methylanilino) ethanethiol, 2- (N-ethylanilino) ethanethiol 2- (2-mercaptoethylmethylamino) -ethanethiol, cyclopentyl mercaptan, cyclohexyl mercaptan, mercapto-1,4-dithiane, mercaptomethyl-1,4-dithiane, mercaptoethylthiomethyl-1, 4-dithiane, thiophenol, 4-hydroxythiophenol, 2-methylthiophenol, 3-methylthiophenol, 4-methylthiophenol, 4-t-butylthiophenol, 2,4-dimethylthiophenol, 2,5-dimethylthio Phenol, 3-methoxythiophenol, 4-methoxythiophenol, 5-t-butyl-2-methylthiophenol, 2-chlorothiophenol, 3-chlorothiophenol, 4-chlorothiophenol, 2,5-dichlorothiophenol 3,4-dichlorothiophenol, 2,3-dichlorothiophenol, 2,6-dichlorothiophenol, 3,5-dichlorothiophenol, 2,4-dichlorothiophenol, 2,4,5-trichlorothiophenol , Pentachlorothiophenol, -Amino-4-chlorothiophenol, 2-bromothiophenol, 3-bromothiophenol, 4-bromothiophenol, 4-nitrothiophenol, 2-aminothiophenol, 3-aminothiophenol, 4-aminothiophenol Benzyl mercaptan, 4-methoxybenzyl mercaptan, 4-chlorobenzyl mercaptan, 2,4-dichlorobenzyl mercaptan, 4-bromobenzyl mercaptan, 3-vinylbenzyl mercaptan, 4-vinylbenzyl mercaptan, 2-phenylthioethanethiol, 2 -Benzylthioethanethiol, 2-mercaptonaphthalene, 1-mercaptofuran, 2-mercaptofuran, 1-mercaptomethylfuran, 2-mercaptomethylfuran, 1-mercaptothiophene, 2-mer Script thiophene, 1-mercaptomethyl-thiophene, 2-mercaptomethyl-thiophene, 2-mercaptopyridine, 4-mercaptopyridine, 2-mercapto-biphenyl, 4-mercapto-biphenyl, and the like mercapto benzoate. Compound (C) may be used alone or in combination of two or more. Among them, preferred specific examples are thiophenol, 2-methylthiophenol, 3-methylthiophenol, 4-methylthiophenol, benzyl mercaptan, 4-chlorobenzyl mercaptan, 1-mercaptomethylfuran, 2-mercaptoethanol, cyclohexyl mercaptan, A preferred embodiment is benzyl mercaptan.

  The addition amount of the compound (C) is 3% by mass or more and 40% by mass or less, more preferably 5% by mass or more and 20% by mass when the total of the compound (A) and the compound (B) is 100% by mass. It is as follows.

  In addition, when the above material is polymerized and cured, a polymerization catalyst can be added as necessary. Polymerization catalysts include amines, phosphines, quaternary ammonium salts, quaternary phosphonium salts, condensates of aldehydes and amine compounds, salts of carboxylic acids and ammonia, urethanes, thiourethanes, guanidines, Thioureas, thiazoles, sulfenamides, thiurams, dithiocarbamates, xanthates, tertiary sulfonium salts, secondary iodonium salts, mineral acids, Lewis acids, organic acids, silicic acids, tetrafluoride Examples thereof include boric acids, peroxides, azo compounds, and acidic phosphate esters.

These polymerization catalysts may be used alone or in combination of two or more. Among these, preferred specific examples include tetra-n-butylammonium bromide, triethylbenzylammonium chloride, cetyldimethylbenzylammonium chloride, quaternary ammonium salts such as 1-n-dodecylpyridinium chloride, tetra-n-butylphosphonium bromide, Quaternary phosphonium salts such as tetraphenylphosphonium bromide can be mentioned. Among these, further preferred specific examples are triethylbenzylammonium chloride and / or tetra-n-butylphosphonium bromide, and the most preferred specific example is tetra-n-butylphosphonium bromide.
The addition amount of the polymerization catalyst is 0.001% by mass or more and 5% by mass or less, preferably 0.002% by mass or more and 5% by mass with respect to 100% by mass in total of the inorganic compound (A) and the compound (B). Or less, more preferably 0.005 mass% or more and 3 mass% or less.

Furthermore, when the material is polymerized and cured, a polymerization regulator may be added as necessary for the purpose of extending the pot life or dispersing the polymerization heat. Examples of the polymerization regulator include halides of Groups 13 to 16 in the long-term periodic table.
These polymerization regulators may be used alone or in combination of two or more. Of these, preferred are halides of silicon, germanium, tin and antimony. More preferred are chlorides of silicon, germanium, tin and antimony, and further preferred are chlorides of germanium, tin and antimony having an alkyl group. Specific examples of the most preferred are dibutyltin dichloride, butyltin trichloride, dioctyltin dichloride, octyltin trichloride, dibutyldichlorogermanium, butyltrichlorogermanium, diphenyldichlorogermanium, phenyltrichlorogermanium, triphenylantimony dichloride.
The addition amount of the polymerization regulator is 0.001% by mass or more and 5% by mass or less, preferably 0.002% by mass or more and 5% by mass with respect to 100% by mass in total of the compound (A) and the compound (B). Or less, more preferably 0.005 mass% or more and 3 mass% or less.

  Moreover, you may add the prepolymerization reaction catalyst which accelerates | stimulates reaction, when making it pre-react. Examples of the prepolymerization reaction catalyst include the same compounds as the polymerization catalyst described above, among which compounds containing nitrogen or phosphorus atoms are preferred, and compounds containing nitrogen or phosphorus atoms and having an unsaturated bond are more preferred. Particularly preferred are imidazoles, and most preferred is 2-mercapto-1-methylimidazole. The addition amount of the prepolymerization reaction catalyst is 0.001% by mass or more and 5% by mass or less, preferably 0.002% by mass or more and 5% by mass or less with respect to 100% by mass of the total of the compound (A) and the compound (B). It is not more than mass%, and more preferably not less than 0.005 mass% and not more than 3 mass%.

In addition to the above, for the purpose of improving various performances such as oxidation resistance, weather resistance, dyeability, strength, and refractive index, a compound capable of reacting with some or all of the compounds contained in the polymerizable composition is added. It is also possible to cure by polymerization. In this case, a known polymerization catalyst can be added separately as necessary for the reaction.
Compounds that can react with some or all of the compounds contained in the polymerizable composition include compounds having two or more SH groups, epoxy compounds, iso (thio) cyanates, carboxylic acids, and carboxylic acid anhydrides. Phenols, amines, vinyl compounds, allyl compounds, acrylic compounds, methacrylic compounds and the like.
Furthermore, it is of course possible to further improve the practicality of the resulting plastic lens by adding various additives such as known antioxidants, bluing agents, ultraviolet absorbers, deodorants and the like.

[Effects of Embodiment]
According to the plastic lens of the present embodiment as described above, for example, the following operational effects can be achieved.

(1) When a thick plastic lens is formed because a cooling step is performed before a rapid increase in reaction rate occurs, and the temperature of the polymerizable composition is lowered to prevent a local increase in polymerization rate. Also, the occurrence of defects such as optical distortion and striae can be suppressed.
On the other hand, in the holding step corresponding to the initial stage of the polymerization and curing, which is less likely to cause problems, the polymerization is allowed to proceed to a certain degree while maintaining the polymerizable composition at a relatively high initial temperature or higher, so that the conventional manufacturing method has been made low from the initial stage of the polymerization and curing Compared with, the time required for manufacturing can be drastically reduced.
In addition, since the initial temperature can be set so that the viscosity of the polymerizable composition becomes moderate, filling into the molding mold is facilitated, and unevenness does not occur during filling. Leakage of the polymerizable composition and generation of bubbles due to shrinkage of the molding mold can also be prevented.
Therefore, a thick plastic lens free from optical distortion or striae can be manufactured easily and in a short time.

(2) Since the cooling step is performed before gelation, local increase in polymerization rate can be prevented, and optical distortion and striae can be reliably prevented.
(3) Since the cooling step is performed at a time when 15% or more and 80% or less have elapsed since the start of the holding step, gelation starts to progress while the polymerization is progressed in the holding step to shorten the manufacturing time. A cooling step can be performed before.
(4) Since the temperature of the polymerizable composition while gelation proceeds can be maintained at a low temperature by the low temperature maintaining step, it is possible to more reliably prevent the occurrence of optical distortion and striae.

(5) Since the temperature change of the polymerizable composition in the cooling step is set to 5 ° C. or more and 50 ° C. or less, the temperature of the polymerizable composition can be appropriately reduced, and the optical distortion and pulse can be suppressed while suppressing the increase in production time. It is possible to prevent occurrence of reason.
(6) Since the initial temperature is set to 0 ° C. or more and 50 ° C. or less, the polymerizable composition has a viscosity that is easy to handle, and the filling process is facilitated, and unevenness during filling is less likely to occur. In addition, the polymerization rate in the holding step is moderately maintained, and the effect of shortening the production time can be obtained.
(7) Since the temperature of the polymerizable composition is increased in the initial heating step, the polymerization rate can be increased and the time required for producing the plastic lens can be shortened.

(8) In the initial heating step, the polymerizable composition is heated at a temperature rising speed of 0.1 ° C./hour or more and 3.0 ° C./hour or less, thereby causing problems such as leakage of the polymerizable composition. In addition, the polymerization rate can be increased to shorten the time required for manufacturing the plastic lens.
(9) After the gelation is completed by the heating step and the high temperature maintaining step and there is no possibility of occurrence of optical distortion or striae, the polymerizable composition is fully cured to obtain a finished plastic lens. .
(10) Since the above-mentioned composition is polymerized and cured, a resin having a high refractive index can be obtained. Therefore, in this embodiment using these as a polymerizable composition, there is no optical distortion or striae, and there is no high distortion and a thick plastic. A lens can be obtained.

[Modification]
The present invention is not limited to the above-described embodiments, and modifications, improvements, and the like within the scope that can achieve the object of the present invention are included in the present invention.
For example, in the above-described embodiment, the configuration in which the holding process includes the initial overheating process is illustrated, but the present invention is not limited thereto.
In the holding step, the polymerizable composition may be maintained at the initial temperature.
In this case, although the effect of shortening the manufacturing time by the initial heating step cannot be obtained, the expansion and contraction of the molding mold can be prevented, and problems such as leakage of the polymerizable composition can be prevented.

[Example]
Next, examples and comparative examples based on the embodiment of the present invention will be described, but the present invention is not limited thereto.

[Example 1]
A plastic lens was manufactured using the above-described “composition containing an inorganic compound having a sulfur atom or a selenium atom” as a polymerizable composition.

(Preparation of polymerizable composition)
First, 20% by mass of sulfur and 80% by mass of bis (β-epithiopropyl) sulfide were mixed well at 65 ° C. to make uniform.
Next, 0.5% by mass of 2-mercapto-1-methylimidazole was added and reacted at 60 ° C. for about 60 minutes.
Thereafter, the obtained resin composition was cooled to 20 ° C.
On the other hand, 5% by mass of benzyl mercaptan, 0.03% by mass of triethylbenzylammonium chloride and 0.2% by mass of di-n-butyltin dichloride were added and mixed well to obtain a solution A.
And this A solution was added to the above-mentioned cooled composition for resin, and it was set as the uniform polymerizable composition.
Next, the obtained polymerizable composition was degassed under conditions of 10 torr, 10 minutes, and 20 ° C.

(Manufacture of plastic lenses)
Two glass molds for glass molding (glass mold) were used, and the glass molds were arranged to face each other with a minimum thickness of 15 mm, and an adhesive tape was wound around the periphery to form a molding mold.
Many plastic lenses have a thin thickness of about 1 mm, and a thick one has a thickness of 10 to 15 mm. In this example, the plastic lens was manufactured under the condition that the lens thickness is the thickest, the minimum thickness is 15 mm, and optical distortion is likely to occur during the manufacturing process.

The polymerizable composition was poured into the molding mold, and the molding mold was placed in a temperature raising furnace, and a curing process was performed for approximately 25 hours along the temperature pattern shown in FIG.
Thereafter, the cured plastic lens was released from the mold for molding, and was annealed by heating at 130 ° C. for 2 hours.

  In FIG. 1, A to B are holding steps (initial heating step), B to C are cooling steps, C to D are low temperature maintaining steps, D to E are heating steps, and E to F are high temperatures. This is the maintenance process. F to G are cooling for releasing the plastic lens after the curing process.

[Example 2]
A plastic lens was produced using the above-described “composition containing a polyisocyanate compound and a polyol compound” as a polymerizable composition.

(Preparation of polymerizable composition)
In the polymerizable composition of Example 2, 19.6 parts by weight of m-xylylene diisocyanate which is one kind of aromatic polyisocyanate and 29.7 weights of norbornane diisocyanate which is one kind of alicyclic polyisocyanate. Part and 50.7 parts by weight of a polythiol composition mainly composed of 1,1,3,3-tetrakis (mercaptomethylthio) propane, which is a kind of polythiol.
After mixing and stirring the polymerizable composition, 0.1 part by weight of ZelecUN (manufactured by Stepan) as an internal mold release agent and 0.05 part by weight of SEESORB701 (Cipro Kasei Kogyo) as an ultraviolet absorber were further added. And stirred until completely dissolved. Thereafter, 0.01 parts by weight of dibutyltin dichloride was added as a polymerization catalyst, and the mixture was stirred and dissolved well at room temperature, and then deaerated for 30 minutes while stirring under reduced pressure to 5 mmHg.

(Manufacture of plastic lenses)
This polymerizable composition was poured into the same molding mold as in Example 1 in the same manner. The molding mold was placed in a temperature raising furnace, and the curing process was carried out over 28 hours substantially along the temperature pattern shown in FIG.
Thereafter, the cured plastic lens was released from the mold for molding, and was annealed by heating at 130 ° C. for 2 hours.

Example 3
A plastic lens was produced using the above-described “composition containing a compound having a thioepoxy group or the like” as a polymerizable composition.

(Preparation of polymerizable composition)
The polymerizable composition of this Example 3 is composed of 90 parts by weight of bis (2,3-epithiopropyl) disulfide, 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane. And 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane and 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane 10 parts by weight and 1.0 part by weight of SEESORB 701 (Cipro Kasei Kogyo) as an ultraviolet absorber are added and mixed, and then sufficiently stirred to completely disperse or dissolve. Further, in the raw material, as a catalyst N, N-dimethylcyclohexylamine is added in an amount of 0.1 part by weight and sufficiently stirred at room temperature to obtain a uniform solution. Furthermore, this polymerizable composition was deaerated for 30 minutes while reducing the pressure to 5 mmHg and stirring.

(Manufacture of plastic lenses)
This polymerizable composition was poured into the same molding mold as in Example 1 in the same manner. The molding mold was put in a temperature raising furnace, and the curing process was carried out over 21 hours almost along the temperature pattern shown in FIG.
Thereafter, the cured lens was released from the mold for molding, and was annealed by heating at 130 ° C. for 2 hours.

Example 4
A plastic lens was produced using the above-described “composition containing a compound capable of radical polymerization” as a polymerizable composition.

(Preparation of polymerizable composition)
After mixing and stirring 50 parts by weight of diethylene glycol bisallyl carbonate and 50 parts by weight of diallyl isophthalate, 3 parts of benzoyl peroxide was added and mixed well.
(Manufacture of plastic lenses)
This polymerizable composition was poured into the same molding mold as in Example 1 in the same manner. The molding mold was placed in a temperature raising furnace, and the curing process was performed for approximately 16.5 hours along the temperature pattern shown in FIG.
Thereafter, the cured lens was released from the molding mold and annealed by heating at 100 ° C. for 2 hours.

[Comparative Example 1]
The same polymerizable composition as in Example 1 was injected into the same molding mold as in Example 1 in the same manner. The molding mold was placed in a temperature raising furnace, and a curing process that did not include a cooling process was carried out over 18 hours almost along the temperature pattern shown in FIG.
Thereafter, the cured lens was released from the mold for molding, and was annealed by heating at 130 ° C. for 2 hours.

[Comparative Example 2]
The same polymerizable composition as in Example 2 was injected into the same molding mold as in Example 1 in the same manner. The molding mold was put in a temperature raising furnace, and a curing process not including a cooling process was performed over 21 hours almost along the temperature pattern shown in FIG.
Thereafter, the cured lens was released from the mold for molding, and was annealed by heating at 130 ° C. for 2 hours.

[Comparative Example 3]
The same polymerizable composition as in Example 3 was poured into the same molding mold as in Example 1 in the same manner. The molding mold was put in a temperature raising furnace, and a curing process not including a cooling process was performed over 21 hours almost along the temperature pattern shown in FIG.
Thereafter, the cured lens was released from the mold for molding, and was annealed by heating at 130 ° C. for 2 hours.

[Comparative Example 4]
The same polymerizable composition as in Example 4 was poured into the same molding mold as in Example 1 in the same manner. The molding mold was placed in a temperature raising furnace, and a curing process not including a cooling process was performed over 14.5 hours substantially along the temperature pattern shown in FIG.
Thereafter, the cured lens was released from the mold for molding, and was annealed by heating at 130 ° C. for 2 hours.

[Comparative Example 5]
The same polymerizable composition as in Example 1 was injected into the same molding mold as in Example 1 in the same manner. The molding mold was placed in a temperature raising furnace, and a curing process that did not include a cooling process was carried out over 42 hours almost in accordance with the temperature pattern shown in FIG.
Thereafter, the cured lens was released from the mold for molding, and was annealed by heating at 130 ° C. for 2 hours.

[Comparative Example 6]
The same polymerizable composition as in Example 2 was injected into the same molding mold as in Example 1 in the same manner. The molding mold was placed in a temperature raising furnace, and a curing process that did not include a cooling process was carried out over 51 hours almost along the temperature pattern shown in FIG.
Thereafter, the cured lens was released from the mold for molding, and was annealed by heating at 130 ° C. for 2 hours.

[Comparative Example 7]
The same polymerizable composition as in Example 3 was poured into the same molding mold as in Example 1 in the same manner. The molding mold was placed in a temperature raising furnace, and a curing process not including a cooling process was performed over 49 hours substantially along the temperature pattern shown in FIG.
Thereafter, the cured lens was released from the mold for molding, and was annealed by heating at 130 ° C. for 2 hours.

[Comparative Example 8]
The same polymerizable composition as in Example 4 was poured into the same molding mold as in Example 1 in the same manner. The molding mold was placed in a temperature rising furnace, and a curing process not including a cooling process was performed over 28.5 hours substantially along the temperature pattern shown in FIG.
Thereafter, the cured lens was released from the mold for molding, and was annealed by heating at 130 ° C. for 2 hours.

[Evaluation of plastic lens]
The appearance (optical distortion, presence / absence of peeling) of the plastic lenses of Examples 1 to 4 and Comparative Examples 1 to 8 was inspected visually with a mercury lamp.
(Optical distortion)
Light projected from a high-pressure mercury lamp (manufactured by USHIO, UI-100) and transmitted through a plastic lens was projected onto a projection screen. This transmission image was visually observed. “◯” indicates that there is no distortion, “Δ” indicates that there is slight distortion, and “X” indicates that there is much distortion.
(Polymerization peel)
The surface of the plastic lens when released from the molding mold was visually observed and evaluated. The case where unevenness was not observed on the surface was indicated as “◯”, and the case where unevenness was observed as “x”.
The results of these evaluations are shown in Table 1 below.

As shown in Table 1, optical distortion and peeling were not confirmed about the plastic lens manufactured with the manufacturing method of Examples 1-4 which implement the cooling process of this invention.
On the other hand, optical distortion was large in Comparative Example 1, and slight optical distortion was observed in Comparative Examples 2 to 4.
In the case of a conventional plastic lens having a general thickness, optical distortion does not occur even when manufactured with a temperature pattern as in Comparative Examples 1 to 4. However, when manufacturing a thick plastic lens, it turned out that an optical distortion generate | occur | produces in the temperature pattern like Comparative Examples 1-4.
In Comparative Examples 5 to 8, the temperature from the start of polymerization curing to the heating step for main curing is set to a lower temperature than Comparative Examples 1 to 4. For this reason, a local increase in polymerization rate was prevented, and a plastic lens free from optical distortion was obtained. However, since the polymerizable compound is kept at a low temperature for a long time from the start of polymerization to the heating step, it can be seen that the production of the plastic lens has a longer time than Examples 1-4 and Comparative Examples 1-4.
On the other hand, in the manufacturing method of Examples 1-4, an optical distortion can be prevented even if it has thickness by implementing a cooling process. Moreover, an excessive increase in manufacturing time can be prevented by carrying out the holding step.

The generation mechanism of polymerization peeling is considered as follows.
Volume shrinkage occurs when the polymerizable composition changes from a liquid state to a solid state.
If a high temperature is applied while the progress of the reaction is slow and the curing (volume shrinkage) has not yet finished, the cure (volume shrinkage) proceeds at once. When the mold shape cannot follow the volume shrinkage, the curing polymerizable composition is peeled off from the molding mold, and the unevenness generated along with this is considered to be so-called peeling.
In Examples 1-4, even if it implemented the cooling process, generation | occurrence | production of peeling was not seen. Therefore, it is considered that the appearance of the plastic lens does not deteriorate when the cooling process is performed in terms of the presence or absence of peeling.

The figure which shows the temperature pattern of Example 1 which concerns on embodiment of this invention. The figure which shows the temperature pattern of Example 2 which concerns on embodiment of this invention. The figure which shows the temperature pattern of Example 3 which concerns on embodiment of this invention. The figure which shows the temperature pattern of Example 4 which concerns on embodiment of this invention. The figure which shows the temperature pattern of the comparative example 1 which concerns on embodiment of this invention. The figure which shows the temperature pattern of the comparative example 2 which concerns on embodiment of this invention. The figure which shows the temperature pattern of the comparative example 3 which concerns on embodiment of this invention. The figure which shows the temperature pattern of the comparative example 4 which concerns on embodiment of this invention. The figure which shows the temperature pattern of the comparative example 5 which concerns on embodiment of this invention. The figure which shows the temperature pattern of the comparative example 6 which concerns on embodiment of this invention. The figure which shows the temperature pattern of the comparative example 7 which concerns on embodiment of this invention. The figure which shows the temperature pattern of the comparative example 8 which concerns on embodiment of this invention.

Claims (14)

A filling step of filling the mold with the polymerizable composition;
A curing step of curing the polymerizable composition by exposing the molding mold under a predetermined temperature condition, and a method for producing a plastic lens,
The curing step includes
After the filling step, the holding step of keeping the polymerizable composition at or above the initial temperature during the filling step;
A cooling step for cooling the polymerizable composition after the holding step;
A method for producing a plastic lens, comprising: In the manufacturing method of the plastic lens of Claim 1,
The method for producing a plastic lens, wherein the cooling step is performed before gelation of the polymerizable composition. In the manufacturing method of the plastic lens of Claim 1 or Claim 2,
The cooling step is performed when a time of 15% or more and 80% or less has elapsed from the start of the holding step, assuming that the time from the start to the end of the curing step is 100%. Lens manufacturing method. In the manufacturing method of the plastic lens in any one of Claim 1 thru | or 3,
The manufacturing method of the plastic lens characterized by including the low temperature maintenance process of maintaining the temperature of the cooled said polymeric composition after the said cooling process. In the manufacturing method of the plastic lens in any one of Claims 1 thru | or 4,
The method for producing a plastic lens, wherein the temperature change of the polymerizable composition between the start and end of the cooling step is 5 ° C. or more and 50 ° C. or less. In the manufacturing method of the plastic lens in any one of Claim 1 thru | or 5,
The said initial temperature is 0 degreeC or more and 50 degrees C or less. The manufacturing method of the plastic lens characterized by the above-mentioned. In the manufacturing method of the plastic lens in any one of Claims 1 thru | or 6,
In the holding step, the polymerizable composition is maintained at the initial temperature. A method for producing a plastic lens, wherein: In the manufacturing method of the plastic lens in any one of Claim 1 thru | or 6,
The method for producing a plastic lens, wherein the holding step includes an initial heating step of heating the polymerizable composition. In the manufacturing method of the plastic lens of Claim 8,
In the initial heating step, the polymerizable composition is heated at a temperature rising speed of 0.1 ° C./hour or more and 3.0 ° C./hour or less. In the manufacturing method of the plastic lens in any one of Claim 1 thru | or 9,
The curing step includes
A heating step of heating the polymerizable composition to 80 ° C. or higher and 200 ° C. or lower after the polymerizable composition is gelled;
After the heating step, a high temperature maintaining step for maintaining the temperature of the heated polymerizable composition for 5 minutes or more;
A method for producing a plastic lens, comprising: In the manufacturing method of the plastic lens in any one of Claims 1 thru | or 10,
The said polymeric composition contains the compound which has a thioepoxy group or an epoxy group. The manufacturing method of the plastic lens characterized by the above-mentioned. In the manufacturing method of the plastic lens in any one of Claims 1 thru | or 10,
The polymerizable composition includes at least one of a polyisocyanate compound and a polyisothiocyanate compound,
At least one of a polyol compound and a polythiol compound;
A method for producing a plastic lens, comprising: In the manufacturing method of the plastic lens in any one of Claims 1 thru | or 10,
The said polymeric composition contains the compound which has at least any one of an acryl group, a methacryl group, and an allyl group. The manufacturing method of the plastic lens characterized by the above-mentioned. In the manufacturing method of the plastic lens in any one of Claims 1 thru | or 10,
The polymerizable composition is
(A) an inorganic compound having a sulfur atom and / or a selenium atom;
(B) a compound having one or more structures represented by the following general formula (1) in one molecule;
(C) an SH group-containing organic compound having one or more SH groups in one molecule;
A method for producing a plastic lens, comprising:
(Wherein R ¹ is a hydrocarbon having 1 to 10 carbon atoms, R ² , R ³ and R ⁴ are each a hydrocarbon group or hydrogen having 1 to 10 carbon atoms, Y is O, S, Se or Te, l = 0-5, m = 0 or 1, n = 1-5.)