Method for manufacturing optical materials, polymerizable compositions for optical materials, optical material manufacturing systems, methods for manufacturing optical components, films for manufacturing optical components, molds for manufacturing optical components, and cured products.

Abstract

This method for producing an optical material uses a total of 100 parts by mass of two or more different monomers for an optical material and 0.010-2.0 parts by mass of a polymerization catalyst as raw materials to produce an optical material. The method includes: a preparation step for preparing a total of 100 parts by mass of two or more different monomers for an optical material and 0.010-2.0 parts by mass of a polymerization catalyst; and a prepolymerization step for mixing a part of the two or more different monomers for an optical material and at least a part of the polymerization catalyst, and polymerizing at least a part of the part of the two or more different monomers for an optical material so as to obtain a prepolymer, thereby obtaining a mixture containing the prepolymer.

Description

[Technical Field]

[0001] This disclosure relates to a method for manufacturing optical materials, polymerizable compositions for optical materials, optical material manufacturing systems, methods for manufacturing optical components, films for manufacturing optical components, molds for manufacturing optical components, and cured products. [Background technology]

[0002] One method for manufacturing resins used in optical materials for plastic lenses is the casting polymerization method, in which a polymerizable composition containing monomers is injected into a mold and heated to cure. In the casting polymerization method, a polymerizable composition is prepared and degassed, then injected into a mold, heated and cured (polymerization reaction), the product is removed from the mold (release), and annealed to obtain optical materials (e.g., lenses, semi-finished blanks, etc.). In heat curing, to improve the quality of optical materials, polymerization reactions are generally carried out over several hours to tens of hours while gradually increasing the temperature through heating; specifically, this typically takes about 20 to 48 hours. It is also known that a large portion of the total manufacturing process time (for example, 90% of the total time) is spent on polymerization.

[0003] The example in Patent Document 1 describes how a mold into which a polymerizable composition has been injected was gradually heated from 10°C to 120°C, and polymerized over 20 hours to obtain a molded article.

[0004] Furthermore, the example in Patent Document 2 describes how a mold into which a polymerizable composition has been injected was gradually heated from 25°C over 16 hours to 120°C, and then heated at 120°C for 4 hours to obtain a molded body.

[0005] Patent Document 1: International Publication No. 2014 / 027427 Patent Document 2: International Publication No. 2014 / 133111 [Overview of the Initiative] [Problems that the invention aims to solve]

[0006] As mentioned above, conventionally, in the process of manufacturing optical materials, polymerization reactions were carried out over several hours to tens of hours (for example, 20 to 48 hours) while gradually increasing the temperature through heating. On the other hand, when manufacturing optical materials using conventional methods, shortening the heating polymerization time can lead to problems such as insufficient polymerization resulting in the optical material not hardening, or the formation of striations within the optical material even if it hardens, thus degrading the quality of the optical material. Therefore, in the manufacturing of optical materials, there is a need to suppress striations in the resulting optical materials and to shorten the manufacturing time of the optical materials.

[0007] The problem that one embodiment of the first embodiment of this disclosure aims to solve is to provide a method for manufacturing an optical material that can suppress striations in the resulting optical material and shorten the manufacturing time of the optical material, and a polymerizable composition for optical materials used in the above method for manufacturing an optical material. The problem that one embodiment of the second embodiment of this disclosure aims to solve is to provide a method for manufacturing an optical material and an optical material manufacturing system that can suppress U-shaped striations in the resulting optical material. The problem that one embodiment of the third embodiment of this disclosure aims to solve is to provide a method for manufacturing an optical component, a film for manufacturing an optical component, a mold for manufacturing an optical component, and a cured product, which can manufacture an optical component having a smooth outer surface. The problem that one embodiment of the fourth embodiment of this disclosure aims to solve is to provide a method for manufacturing an optical component, a film for manufacturing an optical component, a mold for manufacturing an optical component, and a cured product, which can manufacture an optical component having a smooth outer surface. [Means for solving the problem]

[0008] Specific means for solving the aforementioned problems include the following embodiments. <1> A method for producing an optical material using a total of 100 parts by mass of two or more different monomers for optical materials and 0.010 to 2.0 parts by mass of a polymerization catalyst as raw materials, A preparation step of preparing a total of 100 parts by mass of two or more different monomers for optical materials and 0.010 to 2.0 parts by mass of the polymerization catalyst, A prepolymerization step to obtain a mixture containing the prepolymer by mixing a portion of the two or more different monomers for optical materials and at least a portion of the polymerization catalyst, and polymerizing at least a portion of the two or more different monomers for optical materials to obtain a prepolymer, A method for manufacturing optical materials containing [specific material]. <2> Furthermore, a process for producing a polymerizable composition for optical materials is provided, in which at least the remainder of the two or more different monomers for optical materials is added to the mixture containing the prepolymer to obtain a polymerizable composition for optical materials containing the two or more different monomers for optical materials, the prepolymer, and the polymerization catalyst. The process includes a curing step of curing two or more different monomers for optical materials in the polymerizable composition for optical materials to obtain an optical material which is a cured product of the polymerizable composition for optical materials. <1> A method for manufacturing optical materials as described above. <3> The prepolymerization step is a step of obtaining a mixture containing the prepolymer by mixing a portion of the two or more different monomers for optical materials with all of the polymerization catalyst, and polymerizing at least a portion of the two or more different monomers for optical materials to obtain a prepolymer. <2> A method for manufacturing optical materials as described above. <4> A portion of the two or more different monomers for optical materials comprises the entirety of one of the two or more different monomers for optical materials and a portion of the other monomers for optical materials other than the one monomer. <3> A method for manufacturing optical materials as described above. <5> The prepolymerization step is a step of obtaining a mixture containing the prepolymer by mixing a portion of the two or more different monomers for optical materials and a portion of the polymerization catalyst, and polymerizing at least a portion of the two or more different monomers for optical materials to obtain a prepolymer. The process for producing the polymerizable composition for optical materials is a step of obtaining a polymerizable composition for optical materials containing the two or more different monomers for optical materials, the prepolymer, and the polymerization catalyst by adding at least the remainder of the two or more different monomers for optical materials and the remainder of the polymerization catalyst to a mixture containing the prepolymer. <2> A method for manufacturing optical materials as described above. <6> The two or more different monomers for optical materials include an isocyanate compound (A), A portion of the two or more different monomers for optical materials comprises a portion of isocyanate compound (A), and the remainder of the two or more different monomers for optical materials comprises the remainder of isocyanate compound (A). <5> A method for manufacturing optical materials as described above. <7> A portion of the polymerization catalyst is 5 to 80 parts by mass out of 100 parts by mass of the polymerization catalyst. <5> or <6> A method for manufacturing optical materials as described above. <8> A portion of the two or more different monomers for optical materials is 5 to 95 parts by mass out of 100 parts by mass of the two or more different monomers for optical materials. <2> ~ <7> A method for manufacturing an optical material as described in any one of the following. <9> The process, which is performed after the prepolymerization step and before the manufacturing step of the polymerizable composition for optical materials, further includes a viscosity adjustment step in which the viscosity of the mixture containing the prepolymer, measured with a B-type viscometer at 25°C and 60 rpm, is adjusted to 30 mPa·s to 2000 mPa·s. <2> ~ <8> A method for manufacturing an optical material as described in any one of the following. <10> Furthermore, a second prepolymerization step is performed to obtain a mixture containing the second prepolymer by mixing the remainder of the two or more different monomers for optical materials with the remainder of the polymerization catalyst, and polymerizing at least a portion of the remainder of the two or more different monomers for optical materials to obtain a second prepolymer. By adding the mixture containing the second prepolymer to the mixture containing the prepolymer, a polymerizable composition for an optical material containing the prepolymer, the second prepolymer, and the polymerization catalyst is obtained in a polymerizable composition manufacturing process for an optical material. By curing the prepolymer and the second prepolymer in the polymerizable composition for an optical material, a curing process is carried out to obtain an optical material which is a cured product of the polymerizable composition for an optical material. The method for manufacturing an optical material according to <1>, which includes the above steps. <11> After the polymerizable composition manufacturing process for an optical material and before the curing process, the method further includes a liquid feeding process of feeding the polymerizable composition for an optical material into a casting mold. The method for manufacturing an optical material according to any one of <2> to <10>, wherein the liquid feeding process is a process of feeding the polymerizable composition for an optical material into a casting mold while remixing it in a static mixer. <12> The method for manufacturing an optical material according to any one of <2> to <11>, wherein the curing process includes a process of curing the polymerizable composition for an optical material by allowing it to stand still. <13> The method for manufacturing an optical material according to any one of <2> to <12>, wherein the curing process includes a process of curing the polymerizable composition for an optical material by allowing it to stand still in a closed space. <14> The method for manufacturing an optical material according to any one of <2> to <13>, wherein the curing process includes a process of curing the polymerizable composition for an optical material by allowing it to stand still without heating from the outside. <15> The method for manufacturing an optical material according to any one of <2> to <14>, wherein the curing process includes a process of curing the polymerizable composition for an optical material by allowing it to stand still for 2 to 10 hours. <16> The method for producing an optical material according to any one of <1> to <15>, wherein the two or more different monomers for optical materials contain an isocyanate compound (A) and an active hydrogen compound (B) selected from at least one of a polythiol compound having two or more mercapto groups, a hydroxythiol compound having one or more mercapto groups and one or more hydroxyl groups, a polyol compound having two or more hydroxyl groups, and an amine compound. <17> The method for producing an optical material according to <16>, wherein the isocyanate compound (A) contains at least one of an alicyclic isocyanate compound and an aromatic isocyanate compound. <18> The method for producing an optical material according to any one of <1> to <17>, wherein the polymerization catalyst contains at least one selected from the group consisting of a basic catalyst having a pKa value of 4 to 8 and an organometallic catalyst. <19> The method for producing an optical material according to any one of <1> to <18>, wherein the polymerization catalyst contains at least one selected from the group consisting of an amine-based catalyst and an organotin-based catalyst. <20> The method for producing an optical material according to any one of <1> to <19>, wherein the polymerization catalyst contains at least one selected from the group consisting of 3,5-lutidine, 2,4,6-collidine, triethylenediamine, N,N-dimethylethanolamine, triethylamine, N-ethylmorpholine, dibutyltin dichloride, dimethyltin dichloride, dibutyltin dilaurate, and dibutyltin diacetate. <21> Two or more different monomers for optical materials, A polymerization catalyst, A prepolymer obtained by polymerizing at least two of the two or more different monomers for optical materials, and The polymerization composition for an optical material, wherein the content of the polymerization catalyst is 0.010 parts by mass to 2.0 parts by mass with respect to a total of 100 parts by mass of the two or more different monomers for optical materials and the prepolymer. <22> The polymerization composition for an optical material according to <21>, having a viscosity of 70 mPa·s to 1000 mPa·s measured at 25°C and 60 rpm with a B-type viscometer. <23> A method for producing an optical material using a polymerizable composition for optical materials containing two or more different monomers for optical materials and a polymerization catalyst, A raw material composition preparation step for preparing a first raw material composition and a second raw material composition, A shearing step to produce the polymerizable composition for optical materials by applying shear force to the first raw material composition and the second raw material composition, A stirring step in which stirring force is applied to the polymerizable composition for optical materials, After the stirring step, a casting step is performed in which the polymerizable composition for optical materials is poured into a mold. A curing step in which the polymerizable composition for optical materials is cured by polymerizing two or more different monomers for optical materials in the polymerizable composition for optical materials in the mold, Includes, At least one of the first raw material composition and the second raw material composition comprises a mixture containing the prepolymer. <1> ~ <20> A method for manufacturing an optical material as described in any one of the following. <24> The viscosity Va of the first raw material composition, measured with a B-type viscometer under the conditions of 25°C and 60 rpm, The absolute value V of the difference between the viscosity Vb of the second raw material composition, measured with a B-type viscometer under the conditions of 25°C and 60 rpm, and the other viscosity Vb is within the range of 20 mPa·s to 1500 mPa·s. <23> A method for manufacturing optical materials as described above. <25> The viscosity Va is in the range of 10 mPa·s to 2000 mPa·s. <24> A method for manufacturing optical materials as described above. <26> The first raw material composition comprises at least one compound selected from the group consisting of polyisocyanate compounds, epoxy compounds, and epithio compounds. <23> ~ <25> A method for manufacturing an optical material as described in any one of the following. <27> The second raw material composition contains at least one active hydrogen compound selected from the group consisting of a polythiol compound having two or more mercapto groups, a hydroxythiol compound containing one or more mercapto groups and one or more hydroxyl groups, a polyol compound containing two or more hydroxyl groups, and an amine compound. <23> ~ <26> A method for manufacturing an optical material as described in any one of the following. <28> The viscosity of the polymerizable composition for optical materials in the casting process, measured with a Type B viscometer at 25°C and 60 rpm, is between 10 mPa·s and 1000 mPa·s. <23> ~ <27> A method for manufacturing an optical material as described in any one of the following. <29> The polymerization catalyst satisfies the following condition 1. <23> ~ <28> A method for manufacturing an optical material as described in any one of the following. [Condition 1] -Ea / R is between -7100 and -2900. (Ea is the activation energy calculated by Arrhenius plot from the reaction rate constants of the two or more different monomers for optical materials at two or more different temperatures, and R is the gas constant (8.314 J / mol / K).) <30> The polymerization catalyst includes at least one selected from the group consisting of basic catalysts with a pKa value of 4 to 8 and organometallic catalysts. <23> ~ <29> A method for manufacturing an optical material as described in any one of the following. <31> A system for producing optical materials using a polymerizable composition for optical materials containing two or more different monomers for optical materials and a polymerization catalyst, A shearing section for producing the polymerizable composition for optical materials by applying shear force to the first raw material composition and the second raw material composition, A stirring unit that applies stirring force to the polymerizable composition for optical materials, A casting section for pouring the polymerizable composition for optical materials into a mold, A curing section that cures the polymerizable composition for optical materials by polymerizing two or more different monomers for optical materials in the polymerizable composition for optical materials in the mold, The quantitative liquid delivery unit, Optical material manufacturing systems including <32> Furthermore, the system includes a viscosity control unit that controls the viscosity of the polymerizable composition for optical materials measured at 25°C and 60 rpm in the stirring unit, according to at least one condition selected from the group consisting of the shear force of the shear section, the temperature of the polymerizable composition for optical materials in the stirring section, the optical quality of the cured product obtained by curing the polymerizable composition for optical materials in the curing section, and a characteristic quantity correlated with the viscosity measured at 25°C and 60 rpm using a B-type viscometer for the polymerizable composition for optical materials. <31> Optical material manufacturing system as described above. <33> Furthermore, the system includes a temperature control unit that controls the temperature in the stirring unit according to at least one condition selected from the group consisting of the shear force in the shearing unit, the temperature of the polymerizable composition for optical materials in the stirring unit, the optical quality of the cured product obtained by curing the polymerizable composition for optical materials in the curing unit, and a characteristic quantity that correlates with the viscosity of the polymerizable composition for optical materials measured with a B-type viscometer at 25°C and 60 rpm. <31> or <32> Optical material manufacturing system as described above. <34> A method for manufacturing an optical component, comprising: a space formation step of attaching a film to the outer circumferential surfaces of two mold substrates arranged opposite each other at a predetermined distance apart to form a space surrounded by the two mold substrates and the film; an injection step of injecting a polymerizable composition into the space; and a curing step of curing the polymerizable composition injected into the space to obtain a cured product, wherein the film is a film that peels off completely from glass when attached to glass and subjected to a heat resistance index test at 85°C, and the film has a heat distortion temperature of 70°C or higher. <35> The polymerizable composition exhibits a thickening curve (y=ae) at 25°C. bx The slope of ) is 0.4 or greater. <34> A method for manufacturing optical components as described above. <36> In the curing process, the curing time is 10 hours or less. <34> or <35> A method for manufacturing optical components as described above. <37> The aforementioned film exhibits a glass ball tack test at 80°C, where the distance the glass ball travels is 200 mm or less. <34> ~ <36> A method for manufacturing an optical component as described in any one of the following. <38> In the curing step, as the polymerizable composition hardens, at least one of the two mold substrates moves on the contact surface with the film, and the distance between the mold substrates becomes smaller than the distance between the mold substrates in the space formation step. <34> ~ <37> A method for manufacturing an optical component as described in any one of the following. <39> The polymerizable composition comprises two or more different monomers for optical materials and a polymerization catalyst, wherein the content of the polymerization catalyst is 0.010 parts by mass to 2.0 parts by mass per 100 parts by mass of the total of the two or more different monomers for optical materials, and the viscosity measured with a B-type viscometer at 25°C and 60 rpm is 10 mPa·s to 1000 mPa·s. <34> ~ <38> A method for manufacturing an optical component as described in any one of the following. <40> The polymerizable composition comprises two or more different monomers for optical materials, a polymerization catalyst, and a prepolymer which is a polymer of the two or more different monomers for optical materials and contains polymerizable functional groups. <34> ~ <39> A method for manufacturing an optical component as described in any one of the following. <41> The aforementioned two or more different monomers for optical materials include at least one active hydrogen compound selected from the group consisting of a polythiol compound containing two or more mercapto groups, a hydroxythiol compound containing one or more mercapto groups and one or more hydroxyl groups, a polyol compound containing two or more hydroxyl groups, and an amine compound. <39> or <40> A method for manufacturing optical components as described above. <42> The polymerization catalyst satisfies the following condition 1. <39> ~ <41> A method for manufacturing an optical component as described in any one of the following. [Condition 1] -Ea / R is between -7100 and -2900. (Ea is the activation energy calculated by Arrhenius plot from the reaction rate constants of the two or more different monomers for optical materials at two or more different temperatures, and R is the gas constant (8.314 J / mol / K).) <43> The polymerization catalyst comprises at least one selected from the group consisting of amine-based catalysts and organotin-based catalysts. <39> ~ <42> A method for manufacturing an optical component as described in any one of the following. <44> A film for manufacturing optical components, comprising: attaching a film to the outer circumferential surfaces of two mold substrates arranged opposite each other at a predetermined distance to form a space surrounded by the two mold substrates and the film; placing a polymerizable composition in the space; and curing the polymerizable composition in 10 hours or less to obtain a cured product, wherein the optical component is manufactured by: A film for manufacturing optical components, comprising at least a base layer and an adhesive layer, which completely peels off from glass when attached to glass and subjected to a heat resistance index test at 85°C. <45> A mold for manufacturing an optical component, wherein a film is attached to the outer surfaces of two mold substrates arranged opposite each other at a predetermined distance to form a space surrounded by the two mold substrates and the film, a polymerizable composition is placed in the space, and the polymerizable composition is cured to obtain a cured product, the mold having a main surface diameter of approximately 60 cm to 80 cm. <46> A cured product of two or more different optical monomers, wherein there are no striations of 1.0 mm or longer in length within a radius of 15 mm from the center of the cured product. The outer surface of the cured product is mirror-like, and the shape between the intersection point of one main surface and the outer surface, and the intersection point of the other main surface and the outer surface, is substantially straight. <47> The intersection of one main surface and the outer circumferential surface, and the intersection of the other main surface and the outer circumferential surface, include projections substantially parallel to the outer circumferential surface. <46> The cured product described above. <48> The amine content, as measured by gas chromatography-mass spectrometry, is between 0.03% by mass and 2.5% by mass. <46> or <47> The cured product described above. <49> Contains thiourethane resin <46> ~ <48> A cured product as described in any one of the following. <50> A method for manufacturing an optical component, comprising: a space formation step of attaching a film to the outer circumferential surfaces of two mold substrates arranged opposite each other at a predetermined interval to form a space surrounded by the two mold substrates and the film; an injection step of injecting a polymerizable composition into the space; and a curing step of curing the polymerizable composition injected into the space to obtain a cured product, wherein the film has a heat resistance index of 1 mm or more when attached to glass and subjected to a heat resistance index test at 85°C (excluding cases where it completely peels off from the glass), and the film has a heat distortion temperature of 120°C or less. <51> The polymerizable composition has a thickening curve slope (y=ae) at 25°C. bx ) is 0.4 or higher <50> A method for manufacturing optical components as described above. <52> In the curing process, the curing time is 10 hours or less. <50> or <51> A method for manufacturing optical components as described above. <53> The aforementioned film exhibits a glass ball tack test at 80°C, where the distance the glass ball travels is 200 mm or less. <50> ~ <52> A method for manufacturing an optical component as described in any one of the following. <54> In the curing step, the polymerizable composition injected into the space is cured by being left to stand in a closed system space. <50> ~ <53> A method for manufacturing an optical component as described in any one of the following. <55> The polymerizable composition comprises two or more different monomers for optical materials and a polymerization catalyst, wherein the content of the polymerization catalyst is 0.010 parts by mass to 2.0 parts by mass per 100 parts by mass of the total of the two or more different monomers for optical materials, and the viscosity measured with a B-type viscometer at 25°C and 60 rpm is 10 mPa·s to 1000 mPa·s. <50> ~ <54> A method for manufacturing an optical component as described in any one of the following. <56> The polymerizable composition comprises two or more different monomers for optical materials, a polymerization catalyst, and a prepolymer which is a polymer of the two or more different monomers for optical materials and contains polymerizable functional groups. <50> ~ <55> A method for manufacturing an optical component as described in any one of the following. <57> The aforementioned two or more different monomers for optical materials include at least one active hydrogen compound selected from the group consisting of a polythiol compound containing two or more mercapto groups, a hydroxythiol compound containing one or more mercapto groups and one or more hydroxyl groups, a polyol compound containing two or more hydroxyl groups, and an amine compound. <55> or <56> A method for manufacturing optical components as described above. <58> The polymerization catalyst satisfies the following condition 1. <55> ~ <57> A method for manufacturing an optical component as described in any one of the following. [Condition 1] -Ea / R is between -7100 and -2900. (Ea is the activation energy calculated by Arrhenius plot from the reaction rate constants of the two or more different monomers for optical materials at two or more different temperatures, and R is the gas constant (8.314 J / mol / K).) <59> The polymerization catalyst comprises at least one selected from the group consisting of amine-based catalysts and organotin-based catalysts. <55> ~ <58> A method for manufacturing an optical component as described in any one of the following. <60> A film for manufacturing optical components, comprising: attaching a film to the outer circumferential surfaces of two mold substrates arranged opposite each other at a predetermined distance to form a space surrounded by the two mold substrates and the film; placing a polymerizable composition in the space; and curing the polymerizable composition in 10 hours or less to obtain a cured product, wherein the optical component is manufactured by: A film for manufacturing optical components, comprising at least a base layer and an adhesive layer, wherein when attached to glass and subjected to a heat resistance test at 85°C, the heat resistance index is 1 mm or more (excluding cases where it completely peels off from the glass). <61> A mold for manufacturing an optical component, wherein a film is attached to the outer surfaces of two mold substrates arranged opposite each other at a predetermined distance to form a space surrounded by the two mold substrates and the film, a polymerizable composition is placed in the space, and the polymerizable composition is cured to obtain a cured product, the mold having a main surface diameter of approximately 60 cm to 80 cm. <62> A cured product of two or more different optical monomers, wherein there are no striations of 1.0 mm or longer in length within a radius of 15 mm from the center of the cured product. The outer surface of the cured product is mirror-like, and the shape between the intersection of one main surface and the outer surface, and the intersection of the other main surface and the outer surface, is a concave curve. <63> The intersection of one main surface and the outer circumferential surface, and the intersection of the other main surface and the outer circumferential surface, include projections substantially parallel to the outer circumferential surface. <62> The cured product described above. <64> The amine content, as measured by gas chromatography-mass spectrometry, is between 0.03% by mass and 2.5% by mass. <62> or <63> The cured product described above. <65> Contains thiourethane resin <62> ~ <64> A cured product as described in any one of the following. [Effects of the Invention]

[0009] According to one embodiment of the first embodiment of this disclosure, it is possible to provide a method for manufacturing an optical material that can suppress striations in the resulting optical material and shorten the manufacturing time of the optical material, and a polymerizable composition for optical materials used in the above method for manufacturing an optical material. According to one embodiment of the second embodiment of this disclosure, it is possible to provide a method for manufacturing an optical material and an optical material manufacturing system that can suppress U-shaped striations in the resulting optical material. According to one embodiment of the third embodiment of this disclosure, a method for manufacturing an optical component, a film for manufacturing an optical component, a mold for manufacturing an optical component, and a cured product can be provided, which can manufacture an optical component having a smooth outer surface. According to one embodiment of the fourth embodiment of this disclosure, a method for manufacturing an optical component, a film for manufacturing an optical component, a mold for manufacturing an optical component, and a cured product can be provided that can manufacture an optical component having a smooth outer surface. [Brief explanation of the drawing]

[0010] [Figure 1]This flowchart shows an example of a control routine for acquiring shear force information using a viscosity control unit and a temperature control unit. [Figure 2] This flowchart shows an example of a control routine for acquiring temperature information of a polymerizable composition for optical materials in a stirring section using a viscosity control unit and a temperature control unit. [Figure 3] This flowchart shows an example of a control routine for acquiring information on feature quantities correlated with the viscosity of a polymerizable composition for optical materials using a viscosity control unit and a temperature control unit. [Figure 4] This flowchart shows an example of a control routine for acquiring optical quality information of a cured product using a viscosity control unit and a temperature control unit. [Figure 5] This is a schematic diagram illustrating an example of an optical material manufacturing system. [Figure 6] This figure shows an example of the configuration of a computer that implements a viscosity control unit and a temperature control unit. [Figure 7] This is a schematic diagram illustrating the spatial formation process. [Figure 8] This is a schematic diagram illustrating the injection process. [Figure 9] This is a schematic diagram illustrating the movement of the molded substrate during the curing process. [Figure 10] This is a schematic diagram illustrating the change in film shape during the curing process. [Modes for carrying out the invention]

[0011] In this disclosure, a numerical range represented by "~" means a range that includes the numbers written before and after "~" as the lower and upper limits, respectively. In this disclosure, the amount of each component in a composition means the total amount of any multiple substances present in the composition, unless otherwise specified, if there are multiple substances corresponding to each component in the composition. In numerical ranges described in stages within this disclosure, the upper or lower limit of one numerical range may be replaced with the upper or lower limit of another numerical range described in stages. Furthermore, in numerical ranges described within this disclosure, the upper or lower limit of that range may be replaced with the values ​​shown in the examples. In this disclosure, the term "process" includes not only independent processes but also processes that cannot be clearly distinguished from other processes, as long as their intended purpose is achieved.

[0012] This disclosure includes the following first to fourth embodiments. Each embodiment will be described in detail.

[0013] [First Embodiment] ≪Method for manufacturing optical materials≫ The first embodiment of the method for producing an optical material is a method for producing an optical material using a total of 100 parts by mass of two or more different monomers for optical materials and 0.010 to 2.0 parts by mass of a polymerization catalyst as raw materials, comprising: a preparation step of preparing a total of 100 parts by mass of two or more different monomers for optical materials and 0.010 to 2.0 parts by mass of a polymerization catalyst; and a prepolymerization step of mixing a portion of the two or more different monomers for optical materials with at least a portion of the polymerization catalyst, and polymerizing at least a portion of the portion of the two or more different monomers for optical materials to obtain a prepolymer, thereby obtaining a mixture containing the prepolymer.

[0014] The method for manufacturing the optical material according to the first embodiment includes a preparation step and a prepolymerization step, which suppresses striations in the resulting optical material and shortens the manufacturing time of the optical material. In the first embodiment, striations refer to a state in which the refractive index of a specific part differs from the normal refractive index of the surrounding area. In optical materials, striations are one of the factors that degrade quality.

[0015] The method for producing an optical material according to the first embodiment further includes, in addition to the above-described preparation step and prepolymerization step, a step for producing a polymerizable composition for optical materials, by adding at least the remainder of the two or more different monomers for optical materials to a mixture containing the prepolymer, thereby obtaining a polymerizable composition for optical materials containing the two or more different monomers for optical materials, the prepolymer, and the polymerization catalyst. Preferably, the method includes a curing step of curing two or more different monomers for optical materials in the polymerizable composition for optical materials to obtain an optical material which is a cured product of the polymerizable composition for optical materials.

[0016] The method for manufacturing the optical material of the first embodiment, by further including a preparation step and a prepolymerization step, a polymerizable composition manufacturing step for optical materials, and a curing step, can more effectively suppress striations in the resulting optical material and more effectively shorten the manufacturing time of the optical material.

[0017] In the preparation step of the first embodiment, the polymerizable composition for optical materials prepared contains a polymerization catalyst in an amount of 0.010 to 2.0 parts by mass per 100 parts by mass of two or more different monomers for optical materials. This amount of polymerization catalyst is higher than that of conventional methods for producing optical materials. This allows the reaction heat (i.e., heat due to self-heating) of the polymerizable composition for optical materials to be generated in a short time when polymerizing the monomers for optical materials in the polymerizable composition for optical materials during the curing process. By utilizing the reaction heat described above, the polymerization reaction of monomers for optical materials in polymerizable compositions for optical materials can be accelerated, making it possible to obtain high-quality optical materials with suppressed striations in a shorter time than conventional methods. Conventionally, when carrying out a polymerization reaction, the polymerizable composition for optical materials was heated to induce the polymerization reaction. However, in the method for producing optical materials of the first embodiment, heating of the polymerizable composition for optical materials is not necessarily required. Furthermore, the method for manufacturing the optical material according to the first embodiment includes a preparation step, a prepolymerization step, a polymerizable composition manufacturing step for optical materials, and a curing step, which makes it possible to suppress convection within the mold in which the polymerization reaction takes place, and to suppress the occurrence of striations in the resulting cured product. Furthermore, the prepolymer in the optical material manufacturing method of the first embodiment can maintain good storage stability. For example, even when the prepolymer is stored for a certain period of time, hardening of the prepolymer can be suppressed. That is, a long pot life can be ensured.

[0018] <Preparation process> The method for producing the optical material according to the first embodiment includes a preparation step of preparing a total of 100 parts by mass of two or more different monomers for optical materials and 0.010 to 2.0 parts by mass of a polymerization catalyst. The number of different monomers for optical materials may be, for example, five or fewer, or three or fewer.

[0019] (Monomers for optical materials) Two or more different monomers for optical materials used in the preparation step are partially used to obtain the prepolymer in the prepolymerization step described later. Furthermore, the remainder of two or more different monomers for optical materials is included in the polymerizable composition for optical materials produced in the polymerizable composition for optical materials manufacturing process described later.

[0020] Examples of monomers for optical materials include isocyanate compounds, polythiol compounds having two or more mercapto groups, hydroxythiol compounds having one or more mercapto groups and one or more hydroxyl groups, polyol compounds having two or more hydroxyl groups, and amine compounds.

[0021] Preferably, two or more different monomers for optical materials include an isocyanate compound (A) and an active hydrogen compound (B) which is at least one selected from the group consisting of a polythiol compound having two or more mercapto groups, a hydroxythiol compound having one or more mercapto groups and one or more hydroxyl groups, a polyol compound having two or more hydroxyl groups, and an amine compound.

[0022] [Isocyanate compound (A)] Examples of isocyanate compounds (A) include aliphatic isocyanate compounds, alicyclic isocyanate compounds, aromatic isocyanate compounds, heterocyclic isocyanate compounds, etc., and are used individually or in combination of two or more. These isocyanate compounds may include dimers, trimers, and prepolymers. Examples of these isocyanate compounds include those exemplified in International Publication No. 2011 / 055540. In the first embodiment, the alicyclic isocyanate compound refers to an isocyanate compound that includes an alicyclic structure and may also include structures other than alicyclic structures, such as heterocyclic structures. Aromatic isocyanate compounds refer to isocyanate compounds that contain an aromatic structure and may also contain one or a combination thereof of an aliphatic structure, an alicyclic structure, and a heterocyclic structure. Heterocyclic isocyanate compounds refer to isocyanate compounds that contain a heterocyclic structure but do not contain alicyclic or aromatic structures. Aliphatic isocyanate compounds refer to isocyanate compounds that do not contain aromatic, alicyclic, or heterocyclic structures.

[0023] The isocyanate compound (A) preferably includes at least one selected from aliphatic isocyanate compounds, alicyclic isocyanate compounds, aromatic isocyanate compounds, and heterocyclic isocyanate compounds, and more preferably includes at least one of alicyclic isocyanate compounds and aromatic isocyanate compounds.

[0024] In the first embodiment, from the viewpoint of suppressing striations in the optical material and shortening the manufacturing time of the optical material, the isocyanate compound (A) preferably contains at least one selected from 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, m-xylylene diisocyanate, 2,4-tole diisocyanate, 2,6-tole diisocyanate, dicyclohexylmethane diisocyanate, 1,3-bis(isocyanatomethyl)cyclohexane, 1,4-bis(isocyanatomethyl)cyclohexane, isophorone diisocyanate, 1,6-hexamethylene diisocyanate, and 1,5-pentamethylene diisocyanate. It is more preferable to include at least one selected from 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, m-xylylene diisocyanate, dicyclohexylmethane diisocyanate, and 1,3-bis(isocyanatomethyl)cyclohexane. It is even more preferable to include at least one selected from m-xylylene diisocyanate, 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, and 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane.

[0025] [Active hydrogen compounds] Examples of active hydrogen compounds include polythiol compounds having two or more mercapto groups, hydroxythiol compounds having one or more mercapto groups and one or more hydroxyl groups, polyol compounds having two or more hydroxyl groups, and amine compounds. As the active hydrogen compound, oligomers of the above-mentioned active hydrogen compound or halogen-substituted derivatives of the above-mentioned active hydrogen compound (e.g., chlorine-substituted derivatives, bromine-substituted derivatives, etc.) may be used. Furthermore, the active hydrogen compounds may be used individually or in mixtures of two or more types.

[0026] (Polythiol compounds having two or more mercapto groups) Polythiol compounds are compounds having two or more mercapto groups, and examples include those exemplified in International Publication No. 2016 / 125736. In the first embodiment, from the viewpoint of suppressing striations in the optical material and shortening the manufacturing time of the optical material, the polythiol compound is 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, penta Preferably, it contains at least one selected from erythritol tetrakis(3-mercaptopropionate), bis(mercaptoethyl) sulfide, pentaerythritol tetrakis(2-mercaptoacetate), 2,5-bis(mercaptomethyl)-1,4-dithiane, 1,1,3,3-tetrakis(mercaptomethylthio)propane, 4,6-bis(mercaptomethylthio)-1,3-dithiane, and 2-(2,2-bis(mercaptomethylthio)ethyl)-1,3-dithiane. 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane It is more preferable to include at least one selected from pentaerythritol tetrakis(3-mercaptopropionate), pentaerythritol tetrakis(2-mercaptoacetate), and 2,5-bis(mercaptomethyl)-1,4-dithiane. It is even more preferable to include at least one selected from 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, and pentaerythritol tetrakis(3-mercaptopropionate).

[0027] (Hydroxythiol compounds having one or more mercapto groups and one or more hydroxyl groups) Examples of thiol compounds having a hydroxyl group include 2-mercaptoethanol, 3-mercapto-1,2-propanediol, glycerin bis(mercaptoacetate), 4-mercaptophenol, 2,3-dimercapto-1-propanol, pentaerythritol tris(3-mercaptopropionate), and pentaerythritol tris(thioglycolate), but the list is not limited to these example compounds.

[0028] (Polyol compounds having two or more hydroxyl groups) Examples of polyol compounds include one or more aliphatic or alicyclic alcohols. Specifically, these include linear or branched aliphatic alcohols, alicyclic alcohols, and alcohols obtained by adding at least one substance selected from the group consisting of ethylene oxide, propylene oxide, and ε-caprolactone to these alcohols. More specifically, examples include the compounds exemplified in International Publication No. 2016 / 125736.

[0029] The polyol compound is preferably at least one selected from ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, 1,3-propanediol, 1,2-cyclopentanediol, 1,3-cyclopentanediol, 1,2-cyclohexanediol, 1,3-cyclohexanediol, and 1,4-cyclohexanediol.

[0030] (Amine compounds) Examples of amine compounds include ethylenediamine, 1,2- or 1,3-diaminopropane, 1,2-, 1,3- or 1,4-diaminobutane, 1,5-diaminopentane, 1,6-diaminohexane, 1,7-diaminoheptane, 1,8-diaminooctane, 1,10-diaminodecane, 1,2-, 1,3- or 1,4-diaminocyclohexane, o-, m- or p-diaminobenzene, 3,4- or 4,4'-diaminobenzophenone, 3,4- or 4,4'-diaminodiphenyl ether, 4,4'-diaminodiphenylmethane, 4,4'-diaminodiphenyl sulfide, 3,3' or primary polyamine compounds such as 4,4'-diaminodiphenylsulfone, 2,7-diaminofluorene, 1,5-, 1,8- or 2,3-diaminonaphthalene, 2,3-, 2,6- or 3,4-diaminopyridine, 2,4- or 2,6-diaminotoluene, m- or p-xylylenediamine, isophoronediamine, diaminomethylbicycloheptane, 1,3- or 1,4-diaminomethylcyclohexane, 2- or 4-aminopiperidine, 2- or 4-aminomethylpiperidine, 2- or 4-aminoethylpiperidine, N-aminoethylmorpholine, N-aminopropylmorpholine, etc. Diethylamine, dipropylamine, di-n-butylamine, di-sec-butylamine, diisobutylamine, di-n-pentylamine, di-3-pentylamine, dihexylamine, dioctylamine, di(2-ethylhexyl)amine, methylhexylamine, diallylamine, N-methylallylamine, piperidine, pyrrolidine, diphenylamine Monofunctional secondary amine compounds such as N-methylamine, N-ethylamine, dibenzylamine, N-methylbenzylamine, N-ethylbenzylamine, dicyclohexylamine, N-methylaniline, N-ethylaniline, dinaphthylamine, 1-methylpiperazine, and morpholine; N,N'-dimethylethylenediamine, N,N'-dimethyl-1,2-diaminopropane, N,N'-dimethyl-1,3-diaminopropane, N,N'-dimethyl-1,2-diaminobutane, N,N'-dimethyl-1,3-diaminobutane, N,N'-dimethyl-1,4-diaminobutane, N,N'-dimethyl-1,5-diaminopentane, N,N'-dimethyl-1,6-diaminohexane, N,N'-dimethyl-1,7-diaminoheptane, N,N'-diethylethylenediamine, N,N'-diethyl-1,2-diaminopropane, N,N'-diethyl-1,3-diaminopropane, N,N'-diethyl-1,2-diamino Examples include secondary polyamine compounds such as nobutane, N,N'-diethyl-1,3-diaminobutane, N,N'-diethyl-1,4-diaminobutane, N,N'-diethyl-1,5-diaminopentane, N,N'-diethyl-1,6-diaminohexane, N,N'-diethyl-1,7-diaminoheptane, piperazine, 2-methylpiperazine, 2,5-dimethylpiperazine, 2,6-dimethylpiperazine, homopiperazine, 1,1-di-(4-piperidyl)methane, 1,2-di-(4-piperidyl)ethane, 1,3-di-(4-piperidyl)propane, 1,4-di-(4-piperidyl)butane, and tetramethylguanidine.

[0031] Among the above, it is preferable that the active hydrogen compound (B) includes a polythiol compound having two or more mercapto groups. The content of the polythiol compound having two or more mercapto groups is preferably 60% by mass or more, more preferably 70% by mass or more, and even more preferably 80% by mass or more, based on the total mass of the active hydrogen compound (B).

[0032] Furthermore, in the first embodiment, the total content of 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane and pentaerythritol tetrakis(3-mercaptopropionate) as the active hydrogen compound (B) is preferably 60% by mass or more, more preferably 70% by mass or more, and even more preferably 80% by mass or more, based on the total mass of the active hydrogen compound (B).

[0033] In the composition, the molar ratio of the total number of hydroxyl groups (OH groups) and mercapto groups (SH groups) in the active hydrogen compound to the isocyanate group (NCO group) in the isocyanate compound (A) (NCO group / (OH group + SH group)) is preferably 0.8 to 1.2, more preferably 0.85 to 1.15, and even more preferably 0.9 to 1.1.

[0034] <Polymerization catalyst> At least a portion of the polymerization catalyst used in the preparation step is used to obtain the prepolymer in the prepolymerization step described later.

[0035] There are no particular restrictions on the polymerization catalyst, but for example, basic catalysts, organometallic catalysts, zinc carbamate salts, ammonium salts, sulfonic acids, etc., can be used. The polymerization catalysts described above may be used individually or in appropriate combinations of two or more types.

[0036] (Basic catalyst) Examples of basic catalysts include amine-based catalysts and imidazole-based catalysts. Specifically, tertiary amine catalysts such as triethylenediamine, N,N-dimethylethanolamine, triethylamine, and N-ethylmorpholine, 2-methylpyrazine, pyridine, α-picoline, β-picoline, γ-picoline, 2,6-lutidine, and 3,5-lutidine. Examples include 2,4,6-collidine, 3-chlorpyridine, N,N-diethylaniline, N,N-dimethylaniline, hexamethylenetetramine, quinoline, isoquinoline, N,N-dimethyl-p-toluidine, N,N-dimethylpiperazine, quinaldine, 4-methylmorpholine, triallylamine, trioctylamine, 1,2-dimethylimidazole, and 1-benzyl-2-methylimidazole.

[0037] Among the above, amine-based catalysts are preferred as basic catalysts. Examples of amine-based catalysts include tertiary amine catalysts such as 3,5-lutidine, 2,4,6-collidine, triethylenediamine, N,N-dimethylethanolamine, triethylamine, and N-ethylmorpholine.

[0038] The amine catalyst preferably contains at least one selected from 3,5-lutidine, 2,4,6-collidine, triethylenediamine, N,N-dimethylethanolamine, triethylamine, and N-ethylmorpholine.

[0039] The basic catalyst may also preferably contain a compound represented by the following general formula (2) and / or a compound represented by the following general formula (3).

[0040] [ka]

[0041] In general formula (2), R1 represents a linear alkyl group having 1 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, or a halogen atom. Multiple R1 atoms may be the same or different. Q represents a carbon atom or a nitrogen atom. m represents an integer from 0 to 5.

[0042] [ka]

[0043] In general formula (3), R2, R3, and R4 each independently represent a linear alkyl group having 1 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, or an allyl group.

[0044] As a basic catalyst, a pKa value of 1 to 9 is preferred, more preferably 3 to 8, and even more preferably 4 to 8.

[0045] The pKa value (acid dissociation index) can be measured, for example, by (a) the method described in The Journal of Physical Chemistry vol.68, number 6, page 1560 (1964), (b) a method using a potentiometric automatic titrator manufactured by Kyoto Electronics Manufacturing Co., Ltd. (such as AT-610 (product name)), or (c) the acid dissociation index described in the Chemical Handbook edited by the Chemical Society of Japan (3rd revised edition, June 25, 1984, published by Maruzen Co., Ltd.).

[0046] (organometallic catalyst) Examples of organometallic catalysts include organotin catalysts; organic acid salts of iron, nickel, zinc, etc.; acetylacetonate complexes; catalyst compositions consisting of carboxylate metal compounds and quaternary ammonium salt compounds; catalyst compositions consisting of bicyclic tertiary amine compounds and quaternary ammonium salt compounds; and metal catalysts in which alkoxy groups, carboxyl groups, etc., are coordinated to titanium or aluminum. Among the organometallic catalysts mentioned above, organotin catalysts are preferred. Examples of organotin catalysts include dibutyltin dichloride (DBC), dimethyltin dichloride (DMC), dibutyltin dilaurate (DBTDL), and dibutyltin diacetate.

[0047] It is preferable that the organotin catalyst includes at least one selected from dibutyltin dichloride, dimethyltin dichloride, dibutyltin dilaurate, and dibutyltin diacetate.

[0048] Polymerization catalysts include basic catalysts with a pKa value of 4-8, and organometallic catalysts. It is preferable to include at least one selected from the group.

[0049] The polymerization catalyst may also preferably include at least one selected from amine-based catalysts and organotin-based catalysts.

[0050] The polymerization catalyst may also preferably include at least one selected from the group consisting of 3,5-lutidine, 2,4,6-collidine, triethylenediamine, N,N-dimethylethanolamine, triethylamine, N-ethylmorpholine, dibutyltin dichloride, dimethyltin dichloride, dibutyltin dilaurate, and dibutyltin diacetate.

[0051] In the preparation step, a total of 100 parts by mass of two or more different monomers for optical materials and 0.010 to 2.0 parts by mass of polymerization catalyst are prepared. In other words, the method for producing the optical material of the first embodiment uses 0.010 to 2.0 parts by mass of polymerization catalyst per 100 parts by mass of a total of two or more different monomers for optical materials. As described above, the amount of polymerization catalyst used in the first embodiment is large compared to conventional methods for producing optical materials. This allows for the rapid generation of reaction heat in the polymerizable composition for optical materials during the curing process, when polymerizing the monomers for optical materials within the polymerizable composition. By further utilizing this reaction heat for polymerization, the polymerization reaction can be effectively promoted, resulting in high-quality optical materials with suppressed striations in a shorter time than conventional methods.

[0052] By using 0.010 parts by mass or more of polymerization catalyst with 100 parts by mass of two or more different monomers for optical materials, the polymerization reaction can be effectively promoted, allowing for the production of high-quality optical materials with suppressed striations in a short time. Furthermore, by effectively promoting the polymerization reaction, the release properties when removing the cured product from the mold can be improved. From the above viewpoint, it is preferable to use 0.015 parts by mass or more of polymerization catalyst per 100 parts by mass of two or more different monomers for optical materials, more preferably 0.038 parts by mass or more, even more preferably 0.10 parts by mass or more, and particularly preferably 0.17 parts by mass or more.

[0053] The range of the polymerization catalyst content described above may be appropriately changed depending on the type of monomer and polymerization catalyst used for optical materials. For example, when the monomers for optical materials include 2,5(6)-bis(isocyanatomethyl)-bicyclo-[2.2.1]-heptane, pentaerythritol tetrakis(3-mercaptopropionate), and 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, and the polymerization catalyst includes 3,5-lutidine, it is preferable to use 0.10 parts by mass or more of the polymerization catalyst per 100 parts by mass of two or more different monomers for optical materials, and more preferably 0.17 parts by mass or more.

[0054] For example, if the monomer for optical materials includes m-xylylene diisocyanate, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, and 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, and the polymerization catalyst includes 3,5-lutidine, it is preferable to use 0.015 parts by mass or more of the polymerization catalyst per 100 parts by mass of two or more different monomers for optical materials, and more preferably 0.020 parts by mass or more.

[0055] For example, if the monomer for optical materials contains m-xylylene diisocyanate and 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, and the polymerization catalyst contains 3,5-lutidine, the polymerization catalyst is used in a ratio of 100 parts by mass of two or more different monomers for optical materials. It is preferable to use 0.010 parts by mass or more, and more preferable to use 0.015 parts by mass or more.

[0056] For example, if the monomer for optical materials contains a mixture of dicyclohexylmethane diisocyanate and 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, and 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, and the polymerization catalyst contains 3,5-lutidine, it is preferable to use 1.0 part by mass or more of the polymerization catalyst per 100 parts by mass of two or more different monomers for optical materials, and more preferably 1.5 parts by mass or more.

[0057] For example, if the monomer for optical materials includes 1,3-bis(isocyanatemethyl)cyclohexane, pentaerythritol tetrakis(2-mercaptoacetate), and 2,5-bis(mercaptomethyl)-1,4-dithiane, and the polymerization catalyst includes 3,5-lutidine, it is preferable to use 0.03 parts by mass or more of the polymerization catalyst per 100 parts by mass of two or more different monomers for optical materials, and more preferably 0.07 parts by mass or more.

[0058] By using 2.0 parts by mass or less of polymerization catalyst with 100 parts by mass of two or more different monomers for optical materials, for example, the handling properties when injecting a polymerizable composition for optical materials into a mold can be improved. From the above viewpoint, it is preferable to use a polymerization catalyst in an amount of 1.5 parts by mass or less per 100 parts by mass of two or more different monomers for optical materials. Furthermore, depending on the type of monomer for optical materials and polymerization catalyst, the polymerization catalyst may be used in amounts of 1.0 part by mass or less, 0.3 parts by mass or less, or 0.15 parts by mass or less, per 100 parts by mass of two or more different monomers for optical materials.

[0059] The amount of the polymerization catalyst can be appropriately determined depending on the type of polymerization catalyst, the type and amount of monomers used (isocyanate compounds, active hydrogen compounds, other components, etc.), and the desired shape of the molded product.

[0060] <Prepolymerization process> The method for producing an optical material according to the first embodiment includes a prepolymerization step of mixing a portion of two or more different monomers for optical materials with at least a portion of a polymerization catalyst, and polymerizing at least a portion of the portion of the two or more different monomers for optical materials to obtain a prepolymer, thereby obtaining a mixture containing a prepolymer.

[0061] The inventors of this invention considered that convection caused by an uneven temperature distribution within the mold in which the polymerization reaction takes place is one of the causes of striations in the resulting cured product. Therefore, the inventors focused on producing a prepolymer by prepolymerizing a portion of the monomers for optical materials, and increasing the viscosity of the polymerizable composition for optical materials by including the prepolymer. This makes it possible to suppress convection within the mold. Furthermore, the manufacturing method of the optical material in the first embodiment makes it less likely for a temperature difference to occur between the inside and outside of the mold by preventing self-heating from escaping to the outside. Considering the above points in combination, it is presumed that the method for manufacturing optical materials according to the first embodiment can suppress striations in the resulting cured product.

[0062] In the first embodiment, the method for producing an optical material involves, in the prepolymerization step, including all of one of two or more different monomers for optical materials, a portion of the other monomers other than the aforementioned monomer, and all or part of a polymerization catalyst, thereby obtaining a prepolymer with excellent pot life.

[0063] There are no particular restrictions on the form of "a part of two or more different monomers for optical materials." For example, "a portion of two or more different monomers for optical materials" may refer to a portion of each of the two or more different monomers for optical materials. Furthermore, "a portion of two or more different monomers for optical materials" may refer to one or all of the two or more different monomers for optical materials.

[0064] In the prepolymerization process, the polymerization catalyst may be used partially or entirely. When using a portion of the monomer as a polymerization catalyst, there are no particular restrictions on the form of the "part of the polymerization catalyst," similar to the "part of two or more different monomers for optical materials." For example, "a portion of the polymerization catalyst" may refer to a portion of the polymerization catalyst.

[0065] When a portion is used as a polymerization catalyst, the portion of the polymerization catalyst is preferably 5 to 80 parts by mass, more preferably 10 to 60 parts by mass, and even more preferably 15 to 50 parts by mass, of 100 parts by mass of the polymerization catalyst, from the viewpoint of ensuring a long pot life.

[0066] From the viewpoint of ensuring a long pot life, a portion of the two or more different monomers for optical materials is preferably 5 to 95 parts by mass, more preferably 20 to 80 parts by mass, and even more preferably 30 to 70 parts by mass, out of 100 parts by mass of the two or more different monomers for optical materials.

[0067] Examples of specific embodiments of the prepolymerization process are shown below, but the prepolymerization process in the first embodiment is not limited to the following embodiments.

[0068] (Aspect a) The prepolymerization step of embodiment a is a step of obtaining a mixture containing a prepolymer by mixing a portion of two or more different monomers for optical materials with all of a polymerization catalyst, and polymerizing at least a portion of the portion of the two or more different monomers for optical materials to obtain a prepolymer.

[0069] In embodiment a, it is preferable that a portion of two or more different monomers for optical materials consists of the entirety of one of the two or more different monomers for optical materials and a portion of the other monomers other than the one monomer for optical materials.

[0070] (Aspect b) The prepolymerization step of embodiment b is a step of obtaining a mixture containing a prepolymer by mixing a portion of two or more different monomers for optical materials and a portion of a polymerization catalyst, and polymerizing at least a portion of the portion of the two or more different monomers for optical materials to obtain a prepolymer. If the method for producing the optical material of the first embodiment includes the prepolymerization step of embodiment b, the polymerizable composition production step for optical materials described later is a step of obtaining a polymerizable composition for optical materials containing two or more different monomers for optical materials, a prepolymer, and a polymerization catalyst by adding the remainder of at least two or more different monomers for optical materials and the remainder of a polymerization catalyst to a mixture containing a prepolymer.

[0071] In embodiment b, two or more different monomers for optical materials are isocyanate compounds (A) Preferably, the monomers for optical materials include a portion of the isocyanate compound (A), and the remainder of the monomers for optical materials includes the remainder of the isocyanate compound (A).

[0072] <Viscosity adjustment process> The method for producing the optical material of the first embodiment preferably further includes a viscosity adjustment step, which is performed after the prepolymerization step and before the polymerizable composition production step for optical materials, in which the viscosity (hereinafter simply referred to as viscosity) of the mixture containing the prepolymer, measured with a B-type viscometer at 25°C and 60 rpm, is adjusted to 30 mPa·s to 2000 mPa·s. By ensuring that the viscosity of the mixture containing the prepolymer is within the above range, the viscosity of the polymerizable composition for optical materials produced in the manufacturing process for polymerizable compositions for optical materials can be kept within an appropriate range, from the viewpoint of suppressing striations in the resulting optical material. As a result, striations in the resulting optical material can be suppressed.

[0073] From the above viewpoint, the viscosity of the mixture containing the prepolymer is preferably 40 mPa·s to 2000 mPa·s, and more preferably 50 mPa·s to 1800 mPa·s. Viscosity is measured using a Type B viscometer under conditions of 25°C and 60 rpm (revolutions per minute).

[0074] There are no particular limitations on the method for adjusting the viscosity of a mixture containing a prepolymer. For example, the viscosity of the mixture containing the prepolymer may be adjusted by methods such as heating and stirring.

[0075] The temperature at which the mixture containing the prepolymer is prepared is not particularly limited, as long as it is within the range at which the prepolymer can be obtained through the polymerization reaction. For example, it may be 20°C to 50°C, or 25°C to 45°C. There are no particular restrictions on the stirring time when preparing a mixture containing a prepolymer, as long as it is sufficient to obtain the prepolymer through the polymerization reaction. For example, it could be 30 minutes to 5 hours, or 1 hour to 5 hours.

[0076] A specific method for preparing a mixture containing a prepolymer may be to prepare the mixture while adjusting the viscosity by stirring under conditions of 40°C for 3 hours.

[0077] <Polymerizable composition manufacturing process for optical materials> The method for producing an optical material according to the first embodiment includes a step for producing a polymerizable composition for optical materials, which involves adding the remainder of at least two or more different monomers for optical materials to a mixture containing a prepolymer, thereby obtaining a polymerizable composition for optical materials containing two or more different monomers for optical materials, a prepolymer, and a polymerization catalyst.

[0078] The process for producing a polymerizable composition for optical materials involves adding the remainder of at least two different monomers for optical materials to a mixture containing a prepolymer, thereby obtaining a polymerizable composition for optical materials containing two or more different monomers for optical materials, a prepolymer, and a polymerization catalyst. This prevents polymerization between the prepolymer and the remainder of the two or more different monomers for optical materials until the mixture containing the prepolymer is mixed with the remainder of the two or more different monomers for optical materials. Therefore, by performing the polymerizable composition manufacturing process for optical materials at an appropriate time, it is possible to improve the handling of the polymerizable composition for optical materials when injecting it into a mold, for example. In the process of manufacturing polymerizable compositions for optical materials, a small amount of the prepolymer is used in the mixture. When adding the remainder of two or more different monomers for optical materials, the remainder of the two or more different monomers for optical materials may be mixed in a single step or in multiple steps.

[0079] There are no particular restrictions on the temperature at which the above components are mixed, but it is preferable to mix them at 30°C or lower, and more preferably at room temperature (25°C) or lower. It is preferable to mix the components at a temperature lower than 25°C. However, if the solubility of additives such as internal release agents with the above components is not good, the above components may be heated beforehand to dissolve the additives in them.

[0080] Specific embodiments of the manufacturing process for polymerizable compositions for optical materials include, for example, the following embodiments.

[0081] First, an additive (e.g., an internal mold release agent) is added to a mixture containing a prepolymer to prepare a mixed solution. This mixed solution is stirred at 25°C for 1 hour to completely dissolve each component, and then degassed to obtain the first mixed solution. Furthermore, the remaining monomer for optical materials and, if necessary, the remaining polymerization catalyst are stirred at 25°C for 30 minutes to completely dissolve them and obtain a second mixture. Then, the first and second mixed solutions are mixed, stirred, and degassed to obtain a polymerizable composition for optical materials as a homogeneous solution.

[0082] <Liquid Transfer Process> The method for manufacturing the optical material according to the first embodiment may further include a liquid delivery step of delivering the polymerizable composition for optical materials to a casting mold after the manufacturing step of the polymerizable composition for optical materials and before the curing step. The liquid delivery step may be a step in which the polymerizable composition for optical materials is delivered to a casting mold while being remixed in a stationary mixer. The liquid delivery step may also be a step in which the polymerizable composition for optical materials is delivered to a casting mold while being remixed by a dynamic mixer. This eliminates the non-uniformity of the distribution of the polymerizable composition for optical materials while it is being delivered to the mold, thereby suppressing the striations in the resulting cured product.

[0083] <Polymerizable composition for optical materials> The polymerizable composition for optical materials of the first embodiment comprises two or more different monomers for optical materials, a polymerization catalyst, and a prepolymer obtained by polymerizing at least two of the two or more different monomers for optical materials, wherein the content of the polymerization catalyst is 0.010 parts by mass to 2.0 parts by mass per 100 parts by mass of the total of the two or more different monomers for optical materials and the prepolymer. This makes it possible to increase the reaction heat (i.e., heat due to self-heating) of the polymerizable composition for optical materials when polymerizing the monomers for optical materials in the polymerizable composition for optical materials. By utilizing the heat generated by the above reaction, the polymerization reaction of monomers for optical materials in polymerizable compositions for optical materials can be accelerated, making it possible to obtain high-quality optical materials with suppressed striations in a shorter time than conventional methods. Furthermore, the polymerizable composition for optical materials according to the first embodiment, having the above configuration, can suppress convection within the mold in which the polymerization reaction takes place, and can suppress the occurrence of striations in the resulting cured product.

[0084] In the polymerizable composition for optical materials of the first embodiment, the content of the polymerization catalyst is preferably 0.015 parts by mass or more, more preferably 0.038 parts by mass or more, and 0.10 parts by mass, based on 100 parts by mass of the total of two or more different monomers and prepolymers for optical materials. It is more preferably 0.17 parts by mass or more, and particularly preferably 0.17 parts by mass or more.

[0085] In the polymerizable composition for optical materials of the first embodiment, the content of the polymerization catalyst is preferably 1.5 parts by mass or less, and more preferably 1.0 part by mass or less, based on a total of 100 parts by mass of two or more different monomers and prepolymers for optical materials.

[0086] From the viewpoint of suppressing striations, the polymerizable composition for optical materials of the first embodiment preferably has a viscosity (hereinafter simply referred to as viscosity) of 70 mPa·s or more, more preferably 80 mPa·s or more, even more preferably 100 mPa·s or more, and particularly preferably 120 mPa·s or more, as measured with a B-type viscometer at 25°C and 60 rpm. The polymerizable composition for optical materials of the first embodiment preferably has a viscosity of 1000 mPa·s or less, more preferably 700 mPa·s or less, and even more preferably 400 mPa·s or less, from the viewpoint of maintaining good handling when molding the optical material into a desired shape. The method for measuring viscosity is as described above.

[0087] (Other additives) The polymerizable composition for optical materials of the first embodiment may contain any additives. Optional additives include photochromic compounds, internal mold release agents, bluing agents, and ultraviolet absorbers.

[0088] (Photochromic compounds) Photochromic compounds are compounds whose molecular structure reversibly changes upon irradiation with light of a specific wavelength, and whose absorption properties (absorption spectrum) change accordingly. Examples of photochromic compounds used in the first embodiment include compounds whose absorption characteristics (absorption spectrum) change in response to light of a specific wavelength.

[0089] In the first embodiment, there are no particular restrictions on the photochromic compound, and any conventionally known compound that can be used in photochromic lenses can be appropriately selected and used. For example, one or more compounds can be used from spiropyran compounds, spirooxazine compounds, fulgide compounds, naphthopyran compounds, bisimidazole compounds, etc., depending on the desired coloration.

[0090] The photochromic compounds in the first embodiment include Vivimed's Reversacol Humber Blue (polydimethylsiloxane chain, naphtopyran chromophore), Reversacol Calder Blue (polydimethylsiloxane chain, naphtopyran chromophore), Reversacol Trent Blue (polydimethylsiloxane chain, naphtopyran chromophore), Reversacol Pennine Green (polydimethylsiloxane chain, naphtopyran chromophore), Reversacol Heath Green (polyoxyalkylene chain, naphtopyran chromophore), Reversacol Chilli Red (polydimethylsiloxane chain, naphtopyran chromophore), Reversacol Wembley Grey (polyoxyalkylene chain, naphtopyran chromophore), Reversacol Cayenne Red (polyoxyalkylene chain, naphtopyran chromophore), and Peacock. Examples include Blue (polyoxyalkylene chains, naphthopyran-based chromophores) and Jalapeno Red (polyoxyalkylene chains, naphthopyran-based chromophores), and can be used individually or in combination of two or more types.

[0091] Examples of internal mold release agents include acidic phosphate esters. Examples of acidic phosphate esters include phosphate monoesters and phosphate diesters, which can be used individually or in combination of two or more types.

[0092] Furthermore, when using highly polymerizable monomers for optical materials, it is preferable to use an internal mold release agent with relatively low release properties. Examples of highly polymerizable monomers for optical materials include isocyanate compounds having aromatic rings and trifunctional polythiol compounds (specifically, 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, etc.). These highly polymerizable monomers for optical materials are prone to detaching from the mold earlier than expected (for example, during polymerization of the monomer) (also known as early release). Therefore, when using highly polymerizable monomers for optical materials, the occurrence of early release can be suppressed by using an internal mold release agent with relatively low release properties. As an internal release agent with relatively low release properties, for example, an acidic phosphate ester with relatively low release properties is preferred, and specifically JP-506H (manufactured by Johoku Chemical Industry Co., Ltd.) is more preferred. Furthermore, from the viewpoint of suppressing early release, it is also preferable to reduce the release properties of the monomer for optical materials by adjusting the amount of internal release agent added. Specifically, from the viewpoint of suppressing the occurrence of early release, the content of the internal release agent is preferably 1000 ppm by mass or less.

[0093] Furthermore, there is no particular limit to the timing of adding the internal release agent to a mixture containing a prepolymer, a polymerizable composition for optical materials, etc. The internal release agent may be added during the prepolymerization process, added to the mixture containing the prepolymer after the prepolymerization process, or added to the remainder of two or more different optical material monomers added to the mixture containing the prepolymer.

[0094] When using an internal release agent such as an acidic phosphate ester that may form a salt with the polymerization catalyst, the formation of the salt may reduce the catalytic activity of the polymerization catalyst and prolong the reaction time. Therefore, from the viewpoint of suppressing the extension of the polymerization reaction time in the prepolymerization process, it is preferable not to add the internal release agent while the polymerization reaction is progressing in the prepolymerization process. From the viewpoint of shortening the polymerization reaction time in the prepolymerization process, it is preferable to add the internal release agent to the mixture containing the prepolymer in a stable state after the polymerization reaction has progressed to a certain extent, or to the remainder of two or more different monomers for optical materials.

[0095] Furthermore, from the viewpoint of improving the stability of the prepolymer (for example, improving the pot life), it is preferable to add the internal release agent to the mixture containing the prepolymer when the polymerization reaction during the prepolymerization process is relatively stable or at a time when stability is desired, in order to suppress the activity of the polymerization catalyst in the mixture containing the prepolymer.

[0096] Examples of bluing agents include those that have an absorption band in the orange to yellow wavelength range within the visible light spectrum and have the function of adjusting the hue of optical materials made of resin. More specifically, bluing agents include substances that exhibit blue to purple colors.

[0097] Examples of UV absorbers used include benzophenone-based UV absorbers such as 2,2'-dihydroxy-4-methoxybenzophenone, 2-hydroxy-4-acryloyloxybenzophenone, 2-hydroxy-4-acryloyloxy-5-tert-butylbenzophenone, and 2-hydroxy-4-acryloyloxy-2',4'-dichlorobenzophenone.

[0098] 2-[4-[(2-hydroxy-3-dodecyloxypropyl)oxy]-2-hydro Triazine-based UV absorbers such as [xyphenyl]4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2-[4-(2-hydroxy-3-tridecyloxypropyl)oxy]-2-hydroxyphenyl]-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2-[4-[(2-hydroxy-3-(2'-ethyl)hexyl)oxy]-2-hydroxyphenyl]-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2,4-bis(2-hydroxy-4-butyloxyphenyl)-6-(2,4-bis-butyloxyphenyl)-1,3,5-triazine, 2-(2-hydroxy-4-[1-octyloxycarbonylethoxy]phenyl)-4,6-bis(4-phenylphenyl)-1,3,5-triazine,

[0099] 2-(2H-benzotriazol-2-yl)-4-methylphenol, 2-(2H-benzotriazol-2-yl)-4-tert-octylphenol, 2-(2H-benzotriazol-2-yl)-4,6-bis(1-methyl-1-phenylethyl)phenol, 2-(2H-benzotriazol-2-yl)-4,6-di-tert-pentylphenol, 2-(5-chloro-2H-benzotriazol-2-yl)-4-methyl-6-tert-butylphenol, 2-(5-chloro-2H-benzotri Examples of benzotriazole-based UV absorbers include zole-2-yl)-2,4-tert-butylphenol and 2,2'-methylenebis[6-(2H-benzotriazole-2-yl)-4-(1,1,3,3-tetramethylbutyl)phenol], but preferred examples include benzotriazole-based UV absorbers such as 2-(2H-benzotriazole-2-yl)-4-tert-octylphenol and 2-(5-chloro-2H-benzotriazole-2-yl)-4-methyl-6-tert-butylphenol. These UV absorbers can be used alone or in combination of two or more.

[0100] <Curing process> The method for producing an optical material according to the first embodiment includes a curing step in which two or more different monomers for optical materials in a polymerizable composition for optical materials are cured to obtain an optical material which is a cured product of the polymerizable composition for optical materials. The method for manufacturing the optical material of the first embodiment includes a curing step, which allows the polymerizable composition for optical materials to be polymerized to obtain a cured product, and this cured product can be used as an optical material. Conventionally, when carrying out a polymerization reaction, the polymerizable composition for optical materials was heated to generate the polymerization reaction. However, the polymerizable composition for optical materials in the first embodiment can accelerate the polymerization reaction of the monomers for optical materials in the polymerizable composition for optical materials by increasing the reaction heat (i.e., heat due to self-heating) associated with the polymerization reaction. In the method for producing optical materials according to the first embodiment, heating of the polymerizable composition for optical materials may be performed, but from the above viewpoint, heating of the polymerizable composition for optical materials is not required. In other words, in the curing step of the first embodiment, the polymerizable composition for optical materials can be cured by polymerization by allowing it to stand.

[0101] As described above, the curing step may include a step of curing the polymerizable composition for optical materials by allowing it to stand. Furthermore, from the viewpoint of curability, during the curing process, the polymerizable composition for optical materials may be left to stand in a closed system space or in an open system space, but it is preferable to leave it to stand in a closed system space. A closed system space refers to an environment in which heat is retained internally and heat conduction between the inside and outside is suppressed. An environment in which heat conduction between the inside and outside is suppressed means that when a polymerizable composition for optical materials is left standing in a closed system space, the heat conductivity between the inside and outside of the closed system space is sufficient to cure the polymerizable composition for optical materials. An example of a closed space is an insulated environment. An open space refers to any space other than a closed space.

[0102] The curing step preferably includes a step of curing the polymerizable composition for optical materials by allowing it to stand in a closed system space. By allowing a polymerizable composition for optical materials to stand in a closed system space, the heat generated by the self-heating of the polymerizable composition for optical materials can be prevented from being released to the outside. As a result, the heat generated by self-heating can be retained within the closed system space, which can promote the polymerization reaction more efficiently and enable the manufacture of optical materials in a shorter time.

[0103] In the "thermal insulation" or "thermal insulation environment" of the first embodiment, it is preferable to heat the adiabatic reaction vessel to a constant temperature state (constant temperature reaction vessel) within a range that does not hinder the polymerization reaction of the polymerizable composition for optical materials due to the reaction heat or excessively accelerate the polymerization reaction of the polymerizable composition for optical materials by external heating. This allows the ambient temperature inside the reaction vessel (constant temperature reaction vessel) where the mold is placed to be maintained at a constant temperature or a warm temperature, depending on the temperature rise due to the self-heating of the monomer for optical materials, thereby promoting the polymerization reaction more effectively.

[0104] For example, an insulated reaction vessel or a constant-temperature reaction vessel, as described above, can be used as an insulated environment. For example, when a mold into which monomers have been injected is placed in a vacuum vessel which is an adiabatic reaction vessel, adiabatic polymerization in an adiabatic environment using an adiabatic reaction vessel (constant temperature reaction vessel) can be carried out by the following procedure. The inner surface of the vacuum container is covered with a heat-insulating or heat-retaining material such as urethane foam or cork, and the mold into which the monomer has been injected is wrapped in a cloth or other material as needed. Then, the mold into which the monomer has been injected is left to stand in the vacuum container.

[0105] The curing step may include a step of curing the polymerizable composition for optical materials by allowing it to stand without external heating (i.e., a non-heating step). As described above, in the method for manufacturing optical materials of the first embodiment, heating of the polymerizable composition for optical materials may be performed, but heating of the polymerizable composition for optical materials is not necessarily required. External heating may require the use of equipment, which can increase the economic burden. The optical material manufacturing method of the first embodiment allows for the simple production of optical materials, thus reducing the economic burden.

[0106] The curing step preferably includes a step of curing the polymerizable composition for optical materials by allowing it to stand for 2 to 10 hours. According to conventional methods, polymerization reactions are generally carried out over several hours to tens of hours (for example, 20 to 48 hours) while gradually increasing the temperature through heating. If the polymerization reaction time is too short, the polymerizable composition for optical materials may not fully cure, making it impossible to obtain the optical material, or the quality of the optical material may deteriorate. However, according to the method for manufacturing optical materials of the first embodiment, it is possible to manufacture optical materials in a short time while suppressing striations in the resulting optical materials. Specifically, optical materials can be manufactured by letting a polymerizable composition for optical materials stand for 10 hours or less. From the above perspective, it is more preferable to allow the polymerizable composition for optical materials to stand for 8 hours or less during the curing process. Furthermore, from the viewpoint of obtaining an optical material that has undergone polymerization and hardened well, it is preferable to allow the polymerizable composition for optical materials to stand for 2 hours or more.

[0107] In the curing process, a microwave irradiation step may be provided, if necessary, in which microwaves are irradiated onto the polymerizable composition for optical materials for a predetermined time.

[0108] One embodiment of the curing process includes the following steps a and b. Step a: The polymerizable composition for optical materials is injected (cast) into the mold (into the cavity of the mold). Step b: The mold into which the polymerizable composition for optical materials has been injected is allowed to stand for a predetermined time to cure.

[0109] (Step a) First, the polymerizable composition is injected into a molding mold (casting mold) held in place by a gasket or tape. Depending on the required properties of the resulting optical material, it is preferable to perform degassing under reduced pressure, filtration under pressure or reduced pressure, etc., as needed.

[0110] (Step b) As described above, in step b, the mold into which the polymerizable composition for optical materials has been injected may be left to stand in an open space for a predetermined time to polymerize, or it may be left to stand in a closed space for adiabatic polymerization.

[0111] While the polymerization conditions are not limited, it is preferable to adjust them as appropriate depending on the composition of the polymerizable composition for optical materials, the type and amount of catalyst used, the shape of the mold, etc. The mold into which the polymerizable composition for optical materials has been injected may be left to stand in an insulating environment for 2 to 4 hours to polymerize.

[0112] In step b, if necessary, a heating step may be added after an adiabatic polymerization process in which the mold into which the polymerizable composition for optical materials has been injected is left to stand in an adiabatic environment for a certain period of time. In step b, if necessary, in parallel with the step of leaving the mold into which the polymerizable composition for optical materials has been injected in an adiabatic environment (adiabatic polymerization), the mold into which the polymerizable composition for optical materials has been injected may be heated continuously or intermittently at a temperature that does not exceed the self-heating generated by the polymerizable composition for optical materials in the adiabatic polymerization process, or the inside of the adiabatic reaction vessel may be heated to maintain the ambient temperature inside the adiabatic reaction vessel.

[0113] The curing step may include a step of heating and curing the polymerizable composition for optical materials (i.e., a heating step). As described above, in the method for manufacturing optical materials of the first embodiment, heating of the polymerizable composition for optical materials is not necessarily required, but the curing step may include the above-mentioned heating step. In other words, the curing process in the first embodiment may be a combination of a non-heating process and a heating process.

[0114] If the curing process includes a heating process, the heating process is preferably carried out for 1% to 40% of the total curing process duration, and more preferably for 1% to 35% of the total curing process duration.

[0115] <Second prepolymerization process> The method for producing the optical material of the first embodiment further includes, in addition to the preparation step and prepolymerization step described above, a second prepolymerization step in which the remainder of the two or more different monomers for optical materials and the remainder of the polymerization catalyst are mixed, and at least a portion of the remainder of the two or more different monomers for optical materials is polymerized to obtain a second prepolymer, thereby obtaining a mixture containing the second prepolymer. A process for producing a polymerizable composition for optical materials, comprising adding a mixture containing the second prepolymer to a mixture containing the first prepolymer, thereby obtaining a polymerizable composition for optical materials containing the first prepolymer, the second prepolymer, and the polymerization catalyst, A curing step to obtain an optical material which is a cured product of the polymerizable composition for optical materials by curing the prepolymer and the second prepolymer in the polymerizable composition for optical materials. It may include ,.

[0116] The method for manufacturing the optical material according to the first embodiment, by including the above configuration, makes it possible to obtain a mixture containing a prepolymer obtained by a prepolymerization step and a mixture containing a second prepolymer obtained by a second prepolymerization step. This allows the viscosity of the mixture containing the prepolymer and the mixture containing the second prepolymer to be brought closer together, making it easier to mix the two.

[0117] In the second prepolymerization step, the two or more different monomers for optical materials, polymerization catalysts, specific embodiments, preferred embodiments, etc. are the same as those in the prepolymerization step.

[0118] In the first embodiment, the method for producing an optical material, when it includes a second prepolymerization step, is a step of producing a polymerizable composition for optical materials, in which a mixture containing the second prepolymer is added to a mixture containing the prepolymer to obtain a polymerizable composition for optical materials containing the prepolymer, the second prepolymer, and the polymerization catalyst. In the above process for manufacturing polymerizable compositions for optical materials, the mixture containing the prepolymer, specific embodiments, preferred embodiments, etc., are the same as those described in the above-mentioned <Process for manufacturing polymerizable compositions for optical materials>.

[0119] In the first embodiment, the method for producing an optical material includes a second prepolymerization step, wherein the curing step is a step of curing the prepolymer and the second prepolymer in the polymerizable composition for optical materials to obtain an optical material which is a cured product of the polymerizable composition for optical materials. In the curing process described above, the prepolymer, specific embodiment, preferred embodiment, etc., are the same as those described in the <curing process> described above.

[0120] <Annealing process> The method for producing the optical material according to the first embodiment may optionally include an annealing step of annealing the cured polymerizable composition for optical materials. The annealing process is typically carried out at a temperature of 50-150°C, but is preferably carried out at 90-140°C, and more preferably at 100-130°C.

[0121] <Optical materials> The optical material in the first embodiment is a cured product of a polymerizable composition for optical materials. The optical material in the first embodiment is a high-quality optical material with suppressed striations.

[0122] Generally, the thicker an optical material is, the more likely it is to develop striations. Optical materials manufactured using the optical material manufacturing method of the first embodiment can effectively suppress striations even when they are relatively thick. For example, the optical material in the first embodiment may have a thickness of 1 mm to 20 mm, or 4 mm to 16 mm.

[0123] <Applications of optical materials> The optical material in the first embodiment can be used in plastic lenses, prisms, optical fibers, information recording substrates, filters, light-emitting diodes, and the like. Among the above, the optical material in the first embodiment can be suitably used in plastic lenses, and more suitably used in plastic lenses for eyeglasses.

[0124] [Second Embodiment] ≪Method for manufacturing optical materials≫ The method for producing an optical material according to the second embodiment is a method for producing an optical material using a polymerizable composition for optical materials containing two or more different monomers for optical materials and a polymerization catalyst, comprising: a raw material composition preparation step of preparing a first raw material composition and a second raw material composition; a shearing step of applying shear force to the first raw material composition and the second raw material composition to produce the polymerizable composition for optical materials; a stirring step of applying stirring force to the polymerizable composition for optical materials; a casting step of pouring the polymerizable composition for optical materials into a mold after the stirring step; and a curing step of curing the polymerizable composition for optical materials by polymerizing the two or more different monomers for optical materials in the polymerizable composition for optical materials in the mold. "Applying shear force to the first and second raw material compositions" means applying force to the first and second raw material compositions, mainly in a direction intersecting the flow direction, while the first and second raw material compositions are flowing. "Applying stirring force to a polymerizable composition for optical materials" means applying force to the polymerizable composition for optical materials while it is flowing, mainly in a direction roughly parallel to and opposite to the flow direction (i.e., the direction from the inlet to the outlet on a hypothetical line connecting the point where the composition enters the stirring process (inlet) and the point where it exits (outlet)), or stopping the flow and stirring the polymerizable composition for optical materials.

[0125] The method for manufacturing the optical material according to the second embodiment, by including the above-described steps, can suppress U-shaped striations in the resulting optical material. U-shaped striations are likely to occur after a certain amount of time has elapsed since the polymerizable composition for optical materials was poured into the mold. The inventors focused on the process of shearing and stirring the first and second raw material compositions from the viewpoint of suppressing U-shaped striations. Furthermore, after continuing to examine the manner and sequence of shearing and stirring, we found that the manufacturing method of the optical material in the second embodiment, with the above configuration including the shearing step and the stirring step, can suppress U-shaped striations in the resulting optical material. The reason for this is presumed to be as follows: It is believed that by applying a force to the first and second raw material compositions in a direction perpendicular to the flow direction while they are flowing, the first and second raw material compositions are sheared and orientation occurs. By applying a force to the obtained polymerizable composition for optical materials in a direction substantially parallel to and opposite to the flow direction while it is flowing, it is possible to homogenize the concentration unevenness before and after the flow direction, and to mitigate or homogenize the orientation. As a result, it is believed that U-shaped striations can be suppressed.

[0126] The polymerizable composition for optical materials in the second embodiment contains two or more different monomers for optical materials and a polymerization catalyst. Furthermore, polymerizable compositions for optical materials are manufactured by applying shear force to the first raw material composition and the second raw material composition. Therefore, the first raw material composition and the second raw material composition, as a whole, comprise two or more different monomers for optical materials and a polymerization catalyst. For example, the first raw material composition and the second raw material composition may each contain different types of monomers for optical materials, and at least one of the first raw material composition and the second raw material composition may contain a polymerization catalyst (see, for example, the Examples section).

[0127] In the second embodiment, it is preferable that at least one of the first raw material composition and the second raw material composition contains a mixture comprising the prepolymer in the first embodiment. More specifically, the method for producing an optical material according to the second embodiment is a method for producing an optical material using a polymerizable composition for optical materials containing two or more different monomers for optical materials and a polymerization catalyst, A raw material composition preparation step for preparing a first raw material composition and a second raw material composition, A shearing step to produce the polymerizable composition for optical materials by applying shear force to the first raw material composition and the second raw material composition, A stirring step in which stirring force is applied to the polymerizable composition for optical materials, After the stirring step, a casting step is performed in which the polymerizable composition for optical materials is poured into a mold. A curing step in which the polymerizable composition for optical materials is cured by polymerizing two or more different monomers for optical materials in the polymerizable composition for optical materials in the mold, Includes, Preferably, at least one of the first raw material composition and the second raw material composition contains a mixture comprising the prepolymer in the first embodiment.

[0128] <Raw material composition preparation process> The raw material composition preparation process is the process of preparing the first raw material composition and the second raw material composition.

[0129] In the raw material composition preparation process, the first raw material composition and the second raw material composition are not particularly limited as long as they contain, in whole, two or more different monomers for optical materials and a polymerization catalyst. The first raw material composition and the second raw material composition may be commercially available products, or they may be prepared by mixing an optical material monomer and a polymerization catalyst. There are no particular restrictions on the method of mixing as described above, and known methods can be used.

[0130] There are no particular restrictions on the temperature at which the above components are mixed, but it is preferable to mix them at 30°C or lower, and more preferably at room temperature (25°C) or lower. From the viewpoint of the pot life of the polymerizable composition for optical materials being prepared, it may be preferable to use a temperature even lower than 25°C. However, if the solubility of additives such as internal release agents with the above components is not good, the above components may be heated beforehand to dissolve the additives in them.

[0131] When mixing the above components, it is preferable to do so under dry, inert gas conditions to prevent moisture from being incorporated into the polymerizable composition for optical materials.

[0132] In the raw material composition preparation process, a polymerization catalyst may be pre-mixed with a portion of two or more different monomers for optical materials, and then the remaining portion of the two or more different monomers for optical materials may be mixed in a single step or in multiple steps. Specific embodiments of the raw material composition preparation process include, for example, the following:

[0133] First, a mixture is prepared by adding a portion of the monomer for optical materials and an additive (e.g., an internal release agent). This mixture is stirred at 25°C for 1 hour to completely dissolve each component. Then, a portion of the remaining monomer for optical materials is added and stirred to obtain a homogeneous solution. This solution is then degassed to obtain the first raw material composition. Then, the remaining monomer for optical materials and the catalyst are stirred at 25°C for 30 minutes to completely dissolve and obtain a homogeneous solution. This solution is then degassed to obtain the second raw material composition.

[0134] <Shearing process> The shearing process is a process for producing polymerizable compositions for optical materials by applying shear force to the first raw material composition and the second raw material composition. In the second embodiment, the force applied in a direction intersecting the flow direction is also referred to as the shear force. In the second embodiment, applying force primarily in a direction intersecting the flow direction is also referred to as "shearing."

[0135] "To make a composition flow" means, for example, by transferring the composition from a tank to a power mixer, or from a power mixer to a stirring tank.

[0136] When shearing, the flow rates of the first and second raw material compositions are preferably 3 g / s or more, more preferably 6 g / s or more, and even more preferably 9 g / s or more, from the viewpoint of suppressing an increase in viscosity of the polymerizable composition for optical materials while increasing productivity. When shearing, the flow rates of the first raw material composition and the second raw material composition are preferably 50 g / s or less, more preferably 45 g / s or less, and even more preferably 40 g / s or less, from the viewpoint of suppressing U-shaped striations in the polymerizable composition for optical materials.

[0137] There are no particular limitations on the method of applying force to the first raw material composition and the second raw material composition in a direction intersecting the flow direction. One example of such a method is to use a power mixer.

[0138] The rotational speed in the shearing process is preferably 200 rpm or higher, more preferably 400 rpm or higher, and even more preferably 500 rpm or higher. The rotational speed in the shearing process is preferably 3000 rpm or less, more preferably 2500 rpm or less, and even more preferably 2000 rpm or less.

[0139] <Polymerizable composition for optical materials> Polymerizable compositions for optical materials are manufactured by applying shear force to a first raw material composition and a second raw material composition. The polymerizable composition for optical materials contains two or more different monomers for optical materials and a polymerization catalyst.

[0140] (Monomers for optical materials) Details regarding specific examples, preferred embodiments, and preferred content of monomers for optical materials in the second embodiment are the same as those regarding specific examples, preferred embodiments, and preferred content of monomers for optical materials in the first embodiment.

[0141] [Isocyanate compound (A)] Details regarding specific examples, preferred embodiments, preferred content, and definitions of isocyanate compound (A) in the second embodiment are the same as those regarding specific examples, preferred embodiments, preferred content, and definitions of isocyanate compound (A) in the first embodiment.

[0142] [Active hydrogen compounds] Details regarding specific examples of active hydrogen compounds, preferred embodiments, preferred content, etc., in the second embodiment are the same as those regarding specific examples of active hydrogen compounds, preferred embodiments, preferred content, etc., in the first embodiment.

[0143] (Polythiol compounds having two or more mercapto groups) Details such as specific examples, preferred embodiments, and preferred content of polythiol compounds having two or more mercapto groups in the second embodiment are the same as details such as specific examples, preferred embodiments, and preferred content of polythiol compounds having two or more mercapto groups in the first embodiment.

[0144] (Hydroxythiol compounds having one or more mercapto groups and one or more hydroxyl groups) Details such as specific examples, preferred embodiments, and preferred content of hydroxythiol compounds having one or more mercapto groups and one or more hydroxyl groups in the second embodiment are the same as details such as specific examples, preferred embodiments, and preferred content of hydroxythiol compounds having one or more mercapto groups and one or more hydroxyl groups in the first embodiment.

[0145] (Polyol compounds having two or more hydroxyl groups) Details regarding specific examples, preferred embodiments, and preferred content of polyol compounds having two or more hydroxyl groups in the second embodiment are the same as those regarding specific examples, preferred embodiments, and preferred content of polyol compounds having two or more hydroxyl groups in the first embodiment.

[0146] (Amine compounds) Details of specific examples of amine compounds in the second embodiment, preferred embodiments, preferred content, (NCO group / (OH group+SH group)), viscosity Va, viscosity difference V, etc. are the same as details of specific examples of amine compounds in the first embodiment, preferred embodiments, preferred content, (NCO group / (OH group+SH group)), viscosity Va, viscosity difference V, etc.

[0147] <Polymerization catalyst> Details regarding specific examples, preferred embodiments, and preferred content of the polymerization catalyst in the second embodiment are the same as those regarding specific examples, preferred embodiments, and preferred content of the polymerization catalyst in the first embodiment.

[0148] (Basic catalyst) Details regarding specific examples of basic contact, preferred embodiments, preferred pKa, etc., in the second embodiment are the same as those regarding specific examples of basic contact, preferred embodiments, preferred pKa, etc., in the first embodiment.

[0149] (organometallic catalyst) Details regarding specific organometallic catalysts and preferred embodiments in the second embodiment are the same as those regarding specific organometallic catalysts and preferred embodiments in the first embodiment.

[0150] The polymerization catalyst preferably satisfies condition 1 below. [Condition 1] -Ea / R is between -7100 and -2900. (Ea is the activation energy calculated by Arrhenius plot from the reaction rate constants of the two or more different monomers for optical materials at two or more different temperatures, and R is the gas constant (8.314 J / mol / K).)

[0151] When the polymerization catalyst satisfies condition 1, variations in the polymerization rate can be suppressed during the polymerization and curing process of the polymerizable composition. As a result, the occurrence of optical distortion and striations is suppressed, and an optical material with excellent appearance can be obtained.

[0152] The value of Ea is calculated using the following method. A property acquisition step involves heating a composition 1 containing a polymerization-reactive compound and a predetermined amount of polymerization catalyst, and maintaining the temperature at multiple temperatures to obtain physical property values ​​1a derived from the functional groups of the polymerization-reactive compound before heating and physical property values ​​1b derived from the remaining functional groups after maintaining the temperature for a predetermined time. A residual functional group calculation step that calculates the residual functional group ratio 1 at multiple temperatures from physical property values ​​1a and 1b, A reaction rate constant calculation step, which involves calculating a reaction rate constant 1 at multiple temperatures based on the reaction rate equation from the residual functional group ratio 1, A fitting step of calculating the activation energy Ea1 and frequency factor A1 from multiple reaction rate constants 1 at the aforementioned temperatures using an Arrhenius plot, By doing this, the value of Ea is calculated. The calculated Ea is used to determine whether the polymerization catalyst satisfies condition 1. The specific aspects of the method for calculating the value of Ea and the method for determining whether or not the polymerization catalyst satisfies condition 1 are the same as the specific aspects described in International Publication No. 2020 / 256057.

[0153] <Agitation process> The stirring step is a step of applying stirring force to the polymerizable composition for optical materials. In the second embodiment, the force applied in a direction substantially parallel to and opposite to the flow direction is also referred to as the stirring force.

[0154] When applying a force in a direction substantially parallel to and opposite to the flow direction, the preferred range of flow velocity of the polymerizable composition for optical materials is the same as the preferred range of flow velocity of the polymerizable composition for optical materials in the <shearing process> described above.

[0155] There are no particular limitations on the method of applying force to a polymerizable composition for optical materials in a direction substantially parallel to or opposite to the flow direction. One example of such a method is to use a stirring tank containing a stirring bar.

[0156] The rotation speed in the stirring process is preferably 50 rpm or higher, more preferably 100 rpm or higher, and even more preferably 200 rpm or higher. The rotation speed in the stirring process is preferably 800 rpm or less, more preferably 700 rpm or less, and even more preferably 600 rpm or less.

[0157] The method for producing the optical material according to the second embodiment, by including a shearing step and a stirring step, allows for the continuous production of a uniform polymerizable composition for optical materials, from the viewpoint of suppressing U-shaped striations in the resulting optical material.

[0158] In the second embodiment, the method for manufacturing the optical material preferably includes a shearing step and a stirring step in that order, from the viewpoint of suppressing U-shaped striations in the resulting optical material. That is, the method for manufacturing an optical material according to the second embodiment is a method for manufacturing an optical material using a polymerizable composition for optical materials containing two or more different monomers for optical materials and a polymerization catalyst, and preferably includes in this order: a raw material composition preparation step of preparing a first raw material composition and a second raw material composition; a shearing step of manufacturing the polymerizable composition for optical materials by applying shear force to the first raw material composition and the second raw material composition; a stirring step of applying stirring force to the polymerizable composition for optical materials; a casting step of pouring the polymerizable composition for optical materials into a mold after the stirring step; and a curing step of curing the polymerizable composition for optical materials by polymerizing the two or more different monomers for optical materials in the polymerizable composition for optical materials in the mold.

[0159] <Filtration process> The method for producing the optical material according to the second embodiment may further include a filtration step of filtering the polymerizable composition for the optical material. The filtration process can be carried out using a filter. For example, a capsule filter can be used as a filter. The filtration accuracy of the filter is preferably between 1.0 μm and 4.5 μm.

[0160] <Second stirring step> The method for producing the optical material according to the second embodiment may further include a second stirring step of stirring the polymerizable composition for the optical material, in addition to the steps described above. The second stirring step is a step to further stir the polymerizable composition for optical materials, in addition to the shearing step and stirring step described above. When the second stirring step is performed, the stirring step described in the above-mentioned <stirring step> is also called the first stirring step. In the second stirring step, one method for stirring the polymerizable composition for optical materials is, for example, to use a static mixer.

[0161] When using a static mixer, the inner diameter of the static mixer is preferably 5 to 8 mm, and more preferably 6 to 8 mm. When using a static mixer, the number of elements of the static mixer is preferably 16 to 48, more preferably 24 to 48.

[0162] <Casting process> The casting process is a process of casting the polymerizable composition for an optical material into a mold after the first or second stirring process. The viscosity of the polymerizable composition for an optical material measured by a B-type viscometer at 25 °C and 60 rpm in the casting process is preferably 10 mPa·s to 1000 mPa·s. The casting process is preferably a process of adjusting the viscosity of the polymerizable composition for an optical material measured by a B-type viscometer at 25 °C and 60 rpm to 10 mPa·s to 1000 mPa·s and casting it into a mold. By adjusting the viscosity of the polymerizable composition for an optical material within the above range and casting it, the viscosity of the polymerizable composition for an optical material can be within an appropriate range, and streaks in the obtained optical material can be suppressed.

[0163] From the above viewpoints, the viscosity of the polymerizable composition for an optical material in the casting process is preferably 10 mPa·s or more, more preferably 40 mPa·s or more, further preferably 70 mPa·s or more, particularly preferably 80 mPa·s or more, even more preferably 100 mPa·s or more, and even further preferably 120 mPa·s or more. The viscosity of the polymerizable composition for an optical material in the casting process is preferably 1000 mPa·s or less, more preferably 700 mPa·s or less, and further preferably 400 mPa·s or less from the viewpoint of maintaining good handling properties when shaping the optical material into a desired shape.

[0164] There is no particular limitation on the method for adjusting the viscosity of the polymerizable composition for an optical material. For example, the viscosity of the polymerizable composition for an optical material may be adjusted by methods such as adding a high-viscosity compound, heating, stirring, etc.

[0165] The casting step may be a step of casting the polymerizable composition for an optical material into a mold by a multi-axis method. Further, it may be a step of casting the polymerizable composition for an optical material into a mold by an immediately-before-casting mixing method.

[0166] In the casting step, the casting method may be manual casting or automatic casting by a machine. The method of automatic casting may be pressure feeding with nitrogen, or may be liquid feeding by a pump (such as a diaphragm pump or a gear pump).

[0167] In the casting step, it is preferable to apply pressure (for example, back pressure) to the polymerizable composition for an optical material using nitrogen or the like and cast the polymerizable composition for an optical material into a mold. Thereby, more preferably, the polymerizable composition for an optical material can be cast into a mold by a multi-axis method.

[0168] <Curing step> The curing step is a step of curing the polymerizable composition for an optical material by polymerizing the two or more different monomers for an optical material in the polymerizable composition for an optical material in the mold. Since the method for producing an optical material according to the second embodiment includes a curing step, the polymerizable composition for an optical material can be polymerized, and an optical material can be produced.

[0169] The method of polymerization is not particularly limited, and a method of generating a polymerization reaction by heating by a known method may also be used. For example, a method of injecting a polymerizable composition into a molded mold (casting mold) held by a gasket or tape or the like and gradually raising the temperature while heating to promote the polymerization reaction may also be used. At this time, depending on the physical properties required for the obtained optical material, it is preferable to perform a defoaming treatment under reduced pressure and a filtration treatment under pressure, reduced pressure, or the like as necessary.

[0170] As a method of polymerization, a method of performing a polymerization reaction without heating may also be used. That is, in the curing step of the second embodiment, the polymerizable composition for optical materials may be cured by polymerization by allowing it to stand.

[0171] The environment in which the curing process is carried out is not particularly limited, and the mold can be heated and cured from outside the mold. However, from the viewpoint of improving optical quality such as striations and polymerization in a short time, it is preferable to cure the polymerizable composition for optical materials by letting it stand in a closed system space. By allowing a polymerizable composition for optical materials to stand in a closed system space, the heat generated by the self-heating of the polymerizable composition for optical materials can be prevented from being released to the outside. As a result, the heat generated by self-heating can be retained within the closed system space, which can promote the polymerization reaction more efficiently and enable the manufacture of optical materials in a shorter time. An example of a closed space is an insulated environment. An insulating environment refers to an environment in which heat is retained internally and heat conduction between the inside and outside is suppressed. An environment in which heat conduction between the inside and outside is suppressed means that when a polymerizable composition for optical materials is left standing in a closed system space, the heat conductivity between the inside and outside of the closed system space is sufficient to cure the polymerizable composition for optical materials.

[0172] An insulated environment can be created, for example, by using insulating materials. In other words, by placing a polymerizable composition for optical materials in an insulated container made of an insulating material, heat can be retained inside the insulated container, and heat conduction between the inside and outside can be suppressed.

[0173] The thermal conductivity of the insulating material is preferably 0.50 W / mK or less, more preferably 0.10 W / mK or less, and even more preferably 0.05 W / mK or less.

[0174] The density of the insulation material is 10 kg / m³. 3 Preferably, it should be 15 kg / m 3It is more preferable that the amount be greater than or equal to 20 kg / m 3 It is even more preferable that the above conditions are met.

[0175] In the "thermal insulation" or "thermal insulation environment" of the second embodiment, it is preferable to heat the adiabatic reaction vessel to a constant temperature state (constant temperature reaction vessel) within a range that does not hinder the polymerization reaction of the polymerizable composition for optical materials due to the reaction heat or excessively accelerate the polymerization reaction of the polymerizable composition for optical materials by external heating. This allows the ambient temperature inside the reaction vessel (constant temperature reaction vessel) where the mold is placed to be maintained at a constant temperature or a warm temperature, depending on the temperature rise due to the self-heating of the monomer for optical materials, thereby promoting the polymerization reaction more effectively.

[0176] For example, an insulated reaction vessel or a constant-temperature reaction vessel, as described above, can be used as an insulated environment. For example, when a mold into which monomers have been injected is placed in a vacuum vessel which is an adiabatic reaction vessel, adiabatic polymerization in an adiabatic environment using an adiabatic reaction vessel (constant temperature reaction vessel) can be carried out by the following procedure. The inner surface of the vacuum container is covered with a heat-insulating and heat-retaining material such as urethane foam or cork, and the mold into which the monomer has been injected is wrapped in a cloth or other material as needed. Then, the mold into which the monomer has been injected is left to stand in the vacuum container.

[0177] The curing step may be a step of curing the polymerizable composition for optical materials by allowing it to stand without external heating. As described above, in the second embodiment, heating of the polymerizable composition for optical materials is not necessarily required. External heating may require the use of equipment, which can increase the economic burden. Methods that do not involve external heating allow for the simpler manufacture of optical materials, thus reducing the economic burden.

[0178] The curing step is preferably a step of curing the polymerizable composition for an optical material by allowing the polymerizable composition for an optical material to stand for 2 to 10 hours. In the curing step, it is more preferable to allow the polymerizable composition for an optical material to stand for 8 hours or less. Also, from the viewpoint of performing a polymerization reaction to obtain an optical material that is cured well, it is preferable to allow the polymerizable composition for an optical material to stand for 2 hours or more, and more preferably to allow it to stand for 3 hours or more.

[0179] In the curing step, if necessary, a microwave irradiation step of irradiating the polymerizable composition for an optical material with microwaves for a predetermined time may be provided.

[0180] As one aspect of the curing step in the second embodiment, the aspect described as one aspect of the curing step in the first embodiment can be mentioned.

[0181] <Annealing step> The method for producing an optical material according to the second embodiment may include an annealing step of annealing the cured polymerizable composition for an optical material, if necessary. The temperature at which the annealing treatment is performed is usually 50 to 150°C, but it is preferably 90 to 140°C, and more preferably 100 to 130°C.

[0182] <Uses of the optical material> The optical material produced by the method for producing an optical material according to the second embodiment can be used for plastic lenses, prisms, optical fibers, information recording substrates, filters, light-emitting diodes, etc. Among these, the optical material can be suitably used for plastic lenses, and more suitably used for plastic lenses for glasses.

[0183] ≪Optical material production system≫ The optical material production system according to the second embodiment is a system for producing an optical material using a polymerizable composition for an optical material containing two or more different monomers for an optical material and a polymerization catalyst, A shearing section for producing the polymerizable composition for optical materials by applying shear force to the first raw material composition and the second raw material composition, A stirring unit that applies stirring force to the polymerizable composition for optical materials, A casting section for pouring the polymerizable composition for optical materials into a mold, A curing section that cures the polymerizable composition for optical materials by polymerizing two or more different monomers for optical materials in the polymerizable composition for optical materials in the mold, Includes a quantitative liquid delivery unit.

[0184] <Shear section> In the shear section, shear force is applied to the first raw material composition and the second raw material composition to produce the polymerizable composition for optical materials. One method for applying force in a direction intersecting the flow direction at the shear section is to use a power mixer. The preferred ranges for the flow rate of the polymerizable composition for optical materials and the rotation speed of the power mixer in the sheared section are the same as the preferred ranges for the flow rate of the polymerizable composition for optical materials and the rotation speed of the power mixer in the <shearing process> described above.

[0185] <Agitation section> In the stirring section, stirring force is applied to the polymerizable composition for optical materials. One method for applying force in the stirring section in a direction approximately parallel to or opposite to the flow direction is to use a stirring tank containing a stirring bar. The preferred ranges for the flow rate of the polymerizable composition for optical materials in the stirring section, the rotation speed of the stirring tank, etc., are the same as the preferred ranges for the flow rate of the polymerizable composition for optical materials and the rotation speed of the stirring tank, etc., in the <stirring step> described above.

[0186] <Casting section> In the casting section, polymerizable compositions for optical materials are poured into molds. Details such as the specific form of casting and the preferred range of viscosity of the polymerizable composition for optical materials in the casting area are the same as the details such as the specific form of casting and the preferred range of viscosity of the polymerizable composition for optical materials in the casting area in the <casting process> described above.

[0187] <Cured part> In the curing section, the polymerizable composition for optical materials is cured by polymerizing two or more different monomers for optical materials in the polymerizable composition for optical materials within the mold. Details regarding the specific and preferred embodiments of the cured portion are the same as those regarding the specific and preferred embodiments of the curing process described above.

[0188] <Quantitative liquid delivery unit> In the quantitative liquid delivery section, the first raw material composition and the second raw material composition are delivered to the shearing section. Specific examples of quantitative liquid delivery units include pumps such as gear pumps and diaphragm pumps. In the quantitative liquid delivery section, the rate at which the first raw material composition and the second raw material composition are delivered to the shearing section may be adjusted as appropriate.

[0189] <Viscosity Control Section> The optical material manufacturing system of the second embodiment preferably further comprises a viscosity control unit that controls the viscosity of the polymerizable composition for optical materials measured at 25°C and 60 rpm in the stirring unit, according to at least one condition selected from the group consisting of a feature quantity correlated with the shear force of the shearing unit, the temperature of the polymerizable composition for optical materials in the stirring unit, the optical quality of the cured product obtained by curing the polymerizable composition for optical materials in the curing unit, and the viscosity of the polymerizable composition for optical materials measured at 25°C and 60 rpm in the stirring unit using a B-type viscometer (hereinafter also referred to simply as viscosity).

[0190] By controlling the viscosity of the polymerizable composition for optical materials in the stirring section according to the above conditions, U-shaped striations can be suppressed more effectively. Furthermore, U-shaped striations can be suppressed more effectively over a longer period of time.

[0191] The optical material manufacturing system of the second embodiment preferably further includes a temperature control unit that controls the temperature in the stirring unit according to at least one condition selected from the group consisting of the shear force of the shearing unit, the temperature of the polymerizable composition for optical materials in the stirring unit, the optical quality of the cured product obtained by curing the polymerizable composition for optical materials in the curing unit, and a characteristic quantity that correlates with the viscosity of the polymerizable composition for optical materials measured with a B-type viscometer at 25°C and 60 rpm.

[0192] By controlling the temperature in the stirring section according to the above conditions, U-shaped striations can be suppressed more effectively. Furthermore, U-shaped striations can be suppressed more effectively over a longer period of time.

[0193] In the viscosity control unit and the temperature control unit, the determination of whether or not the above conditions are met may be made within the manufacturing apparatus, or it may be made outside the manufacturing apparatus by means of an online system or the like. Furthermore, the determination of whether or not the above conditions are met can also be performed using a pre-trained model generated in advance through statistical machine learning.

[0194] In the viscosity control unit and temperature control unit, control other than viscosity and temperature may also be performed. For example, the liquid level of the polymerizable composition for optical materials in the stirring section may be controlled. That is, if the liquid level of the polymerizable composition for optical materials drops, the liquid level is raised by supplying the polymerizable composition for optical materials using a quantitative liquid supply section (e.g., a pump).

[0195] Below, an example of a control routine by the viscosity control unit and temperature control unit will be explained using Figures 1 to 4. Figure 1 is a flowchart showing an example of a control routine when shear force information is acquired by the viscosity control unit and the temperature control unit. Figure 2 is a flowchart showing an example of a control routine when the viscosity control unit and temperature control unit acquire temperature information of the polymerizable composition for optical materials in the stirring unit. Figure 3 is a flowchart showing an example of a control routine for acquiring information on feature quantities correlated with the viscosity of a polymerizable composition for optical materials using a viscosity control unit and a temperature control unit. Figure 4 is a flowchart showing an example of a control routine when acquiring optical quality information of a cured product using a viscosity control unit and a temperature control unit.

[0196] The optical material manufacturing system of the second embodiment begins with preparing a first raw material composition and a second raw material composition, and then the prepared first and second raw material compositions are supplied to a shearing section. The first and second raw material compositions, in whole, contain two or more different monomers for optical materials and a polymerization catalyst. While the first and second raw material compositions are being delivered and flowing, a force is applied to the first and second raw material compositions in a direction intersecting the flow direction.

[0197] In step 200 of Figure 1, the viscosity control unit and the temperature control unit acquire information on the shear force of the shear section. The acquired shear force information is then used for determination in step 210. Specifically, for example, the viscosity control unit and the temperature control unit determine whether the shear force of the shear section is above a certain value. If the shear force at the shear section exceeds a certain value, control is executed in step 220. Specifically, the viscosity control unit reduces the viscosity of the polymerizable composition for optical materials in the stirring section to an appropriate range. Additionally, the temperature control unit raises the temperature in the stirring section to an appropriate range.

[0198] In steps 200 to 220, the viscosity control unit and the temperature control unit control the viscosity of the polymerizable composition for optical materials in the stirring unit (described later) and the temperature in the stirring unit, respectively, according to the shear force in the shear unit. Specifically, in steps 200 to 220, it is determined whether or not the above conditions are met. If they are not met, the viscosity control unit controls the viscosity of the polymerizable composition for optical materials in the stirring section, and the temperature control unit controls the temperature in the stirring section, both within appropriate ranges. After steps 200 to 220 are completed, the sheared polymerizable composition for optical materials is transferred to the stirring section.

[0199] In the stirring section, the polymerizable composition for optical materials is stirred by applying force to the composition in a direction approximately parallel to and opposite to the flow direction while it is flowing, or by temporarily stopping the flow and stirring the polymerizable composition for optical materials.

[0200] In step 230 of Figure 2, the viscosity control unit and the temperature control unit acquire temperature information of the polymerizable composition for optical materials in the stirring section. The acquired temperature information is used for determination in step 240. Specifically, for example, the viscosity control unit and the temperature control unit determine whether the temperature of the polymerizable composition for optical materials in the stirring section is above a certain value. If the temperature of the polymerizable composition for optical materials in the stirring section is above a certain value, control is performed in step 250. Specifically, the viscosity control unit increases the viscosity of the polymerizable composition for optical materials in the stirring section to an appropriate range. Additionally, the temperature control unit lowers the temperature in the stirring section to an appropriate range. By performing the above control, the temperature rise of polymerizable compositions for optical materials can be suppressed. Furthermore, heat generation can also be suppressed by reducing the rotation speed of the shear section during the process.

[0201] In steps 230 to 250, the viscosity control unit and the temperature control unit control the viscosity of the polymerizable composition for optical materials in the stirring unit and the temperature in the stirring unit according to the temperature of the polymerizable composition for optical materials in the stirring unit.

[0202] In step 260 of Figure 3, the viscosity control unit and the temperature control unit acquire information on feature quantities that correlate with the viscosity of the polymerizable composition for optical materials. The acquired information on these feature quantities is then evaluated in step 270. Specifically, it determines whether a characteristic quantity correlated with the viscosity of a polymerizable composition for optical materials deviates from a certain range.

[0203] Characteristics that correlate with the viscosity of a polymerizable composition for optical materials include, for example, the resistance value of the polymerizable composition for optical materials in the stirring section, the refractive index of the polymerizable composition for optical materials in the stirring section, the electrical conductivity of the polymerizable composition for optical materials in the stirring section, and the optical spectrum of the polymerizable composition for optical materials in the stirring section.

[0204] The viscosity control unit and the temperature control unit perform control in step 280 if a characteristic quantity correlated with the viscosity of the polymerizable composition for optical materials deviates from a certain range.

[0205] In the viscosity control unit and temperature control unit, the viscosity of the polymerizable composition for optical materials in the stirring unit may be measured directly, or it may be calculated from a characteristic quantity that correlates with the viscosity of the polymerizable composition for optical materials. One method for calculating the viscosity of a polymerizable composition for optical materials in a stirring section from a feature quantity correlated with the viscosity of the polymerizable composition for optical materials is to calculate the viscosity from the resistance value of the polymerizable composition for optical materials in a stirring section. Specifically, electricity is passed through the polymerizable composition for optical materials using a tester, and a calibration curve of the resistance and viscosity is created. The viscosity is then calculated from the resistance value. Note that as the curing reaction progresses, polymerization progresses, and the resistance value increases. Similarly, a method can be used to calculate viscosity from, for example, the refractive index of the polymerizable composition for optical materials in the stirring section, the electrical conductivity of the polymerizable composition for optical materials in the stirring section, or the optical spectrum of the polymerizable composition for optical materials in the stirring section.

[0206] Specifically, the control performed in step 280 involves, for example, if the above-mentioned feature quantity deviates from a certain range, controlling the viscosity of the polymerizable composition for optical materials in the stirring section by the viscosity control unit and the temperature in the stirring section by the temperature control unit, both within appropriate ranges, in order to control the viscosity calculated from the feature quantity within a certain range.

[0207] Methods for controlling the viscosity of the polymerizable composition for optical materials in the stirring section to an appropriate range include, for example, adjusting the shear force in the shear section, adjusting the stirring force in the stirring section, discarding and replacing a portion of the polymerizable composition for optical materials, and adjusting the liquid delivery rate in the quantitative liquid delivery section of the optical material manufacturing system. A method for discarding and refreshing a portion of a polymerizable composition for optical materials specifically involves, for example, discharging at least a portion of the polymerizable composition for optical materials from the stirring section through the casting section and replacing at least a portion of the polymerizable composition for optical materials.

[0208] Methods for controlling the temperature in the stirring section to an appropriate range include, for example, controlling the rotation speed of the stirring in the stirring section and controlling the temperature of the water bath in the stirring section.

[0209] In the stirring section, after steps 260 to 280 are completed, the polymerizable composition for optical materials is transferred to the casting section.

[0210] In the casting section, the polymerizable composition for optical materials is poured into a mold. Once casting is complete, the polymerizable composition for optical materials is transferred to the curing section. In the curing section, the polymerizable composition for optical materials is cured by polymerizing two or more different monomers for optical materials in the polymerizable composition for optical materials within the mold.

[0211] In step 290 of Figure 4, the viscosity control unit and the temperature control unit acquire optical quality information of the cured product obtained by curing the polymerizable composition for optical materials in the curing unit. Optical quality information for cured products includes, for example, whether or not striations have occurred in the cured product. The acquired optical quality information is evaluated in step 300. Specifically, for example, the viscosity control unit and the temperature control unit determine whether or not striations have occurred in the hardened material. If striations are present in the cured material, control is performed in step 310. Specifically, the viscosity control unit increases or decreases the viscosity of the polymerizable composition for optical materials in the stirring section within an appropriate range. In addition, the temperature control unit raises or lowers the temperature in the stirring section within an appropriate range. In steps 290 to 310, it is determined whether striations have occurred in the cured product obtained by curing the polymerizable composition for optical materials in the curing section. If striations have occurred, the viscosity control unit increases or decreases the viscosity of the polymerizable composition for optical materials in the stirring section, and the temperature control unit increases or decreases the temperature in the stirring section. This routine is completed when step 310 is finished.

[0212] Figure 5 is a schematic diagram illustrating an example of an optical material manufacturing system. In Figure 5, a first raw material composition and a second raw material composition are prepared for producing a polymerizable composition for optical materials. When the first and second raw material compositions are stirred, they become polymerizable compositions for optical materials containing two or more different monomers for optical materials and a polymerization catalyst. Therefore, the first and second raw material compositions only need to become polymerizable compositions for optical materials when stirred, and the first and second raw material compositions as a whole only need to contain two or more different monomers for optical materials and a polymerization catalyst. Furthermore, the first raw material composition and the second raw material composition may also contain a prepolymer obtained by partially polymerizing two or more different monomers for optical materials.

[0213] The first raw material composition prepared above is placed in liquid A tank 1, and the second raw material composition is placed in liquid B tank 2. Then, while adjusting the liquid temperature with chiller 3, the first raw material composition is transferred from liquid A tank 1 to liquid A metering unit 4 (e.g., a gear pump) and the second raw material composition is transferred from liquid B tank 2 to liquid B metering unit 6 (e.g., a gear pump) using nitrogen back pressure or the like. At this time, the transfer speeds of liquid A metering unit 4 and liquid B metering unit 6 may be the same or different. Subsequently, the first raw material composition is sent from the liquid A metering unit 4 via the liquid A flow sensor head 5 to the upper power mixer 8, which is the shearing unit, and the second raw material composition is sent from the liquid B metering unit 6 via the liquid B flow sensor head 7 to the upper power mixer 8, which is the shearing unit. At this stage, the first raw material composition and the second raw material composition are sheared by applying force in a direction intersecting the flow direction using the upper power mixer 8 to obtain a polymerizable composition for optical materials.

[0214] The polymerizable composition for optical materials may be sheared by the upper power mixer 8, filtered by the capsule filter 10, and then sent to the lower power mixer 9, which is the shearing section. Subsequently, the polymerizable composition for optical materials may be sheared in the lower power mixer 9. Furthermore, the polymerizable composition for optical materials may be sheared by multiple power mixers as described above, or it may be sheared by a single power mixer. For example, the polymerizable composition for optical materials may be sheared by the upper power mixer 8 alone. The polymerizable composition for optical materials is sheared by a lower power mixer 9, filtered by a capsule filter 10, and then sent to a stirring tank 11, which is the stirring section. The stirring tank 11 includes a stirrer 12. In the stirring tank 11, the polymerizable composition for optical materials is stirred by applying force in a direction substantially parallel to and opposite to the flow direction. Subsequently, the polymerizable composition for optical materials is further mixed or stirred in the static mixer 13, and then poured into the mold 14, which is the curing section, by the casting section. Then, in mold 14, the polymerizable composition for optical materials is cured by polymerizing two or more different monomers for optical materials in the polymerizable composition for optical materials.

[0215] In Figure 5, the control panel 15 consists of a viscosity control unit and a temperature control unit. The control panel 15 determines whether the above-mentioned conditions are met and measures or calculates the viscosity of the polymerizable composition for optical materials in the stirring section. Depending on the results, the viscosity and temperature can be controlled as described above. For example, by turning on the foot switch 16, at least a portion of the polymerizable composition for optical materials in the stirring section can be discharged from the casting section in order to replace at least a portion of the polymerizable composition for optical materials.

[0216] Figure 6 shows an example of the configuration of a computer that implements a viscosity control unit and a temperature control unit. The viscosity control unit and temperature control unit can be implemented by a computer 60, for example, as shown in Figure 6. The computer 60 implementing the viscosity control unit and temperature control unit comprises a Central Processing Unit (CPU) 61, a memory 62 as a temporary storage area, and a non-volatile storage unit 63. The computer also includes an input / output interface (I / F) 64 to which input / output devices (not shown) are connected, and a read / write (R / W) unit 65 that controls the reading and writing of data to and from the recording medium 68. The computer also includes a network I / F 66 that connects to a network such as the Internet. The CPU 61, memory 62, storage unit 63, input / output I / F 64, R / W unit 65, and network I / F 66 are connected to each other via a bus 67. The storage unit 63 can be implemented by a Hard Disk Drive (HDD), Solid State Drive (SSD), flash memory, etc. The storage unit 63, as a storage medium, stores a program for making the computer function. The CPU 61 reads the program from the storage unit 63, loads it into memory 62, and sequentially executes the processes contained in the program. This realizes each of the control routines shown in Figures 1 to 4 above.

[0217] [Third Embodiment] ≪Method for manufacturing optical components≫ The manufacturing method of the optical component according to the third embodiment includes a space formation step of attaching a film to the outer circumferential surfaces of two mold substrates arranged opposite each other at a predetermined interval to form a space surrounded by the two mold substrates and the film; an injection step of injecting a polymerizable composition into the space; and a curing step of curing the polymerizable composition injected into the space to obtain a cured product, wherein the film is a film that peels off completely from the glass when attached to the glass and subjected to a heat resistance index test at 85°C, and the film has a heat distortion temperature of 70°C or higher. Furthermore, in the curing step, the curing time is preferably 10 hours or less. Furthermore, the polymerizable composition preferably has a viscosity curving curve (y=ae) at 25°C. bx The slope of ) is 0.4 or greater.

[0218] The method for manufacturing an optical member according to the third embodiment, by including the above configuration, can manufacture an optical member having a smooth outer surface. In the third embodiment, "the outer surface is smooth" means, for example, that the outer surface of the cured product is mirror-like, and it is preferable that the shape between the intersection of one main surface and the outer surface, and the intersection of the other main surface and the outer surface, is substantially straight.

[0219] Furthermore, the manufacturing method for the optical component of the third embodiment makes it possible to manufacture an optical component with a smooth outer surface without polishing, or with a small amount of polishing. The film in the third embodiment is a film with relatively weak static adhesive strength. This allows the film to move along the contact surface with the mold substrate when the polymerizable composition is cured and shrinks during the curing process. As a result, phenomena such as indentation or unevenness of the contact surface between the film and the polymerizable composition can be suppressed.

[0220] Furthermore, adhesives in films with relatively weak static tackiness may leach into the polymerizable composition. This leaching of adhesive into the polymerizable composition can cause clouding, voids, and other problems in the resulting cured product. The manufacturing method for the optical component of the third embodiment, by combining the above-described configuration, can effectively suppress the above-described opacity, voids, etc. In particular, in the curing process of the third embodiment, when the curing time is 10 hours or less, the amount of adhesive elution tends to be significantly suppressed, and the above-mentioned clouding, voids, etc. can be suppressed more effectively.

[0221] <Space formation process> The space formation step in the third embodiment is a step of attaching a film to the outer circumferential surface of two mold substrates that are arranged facing each other at a predetermined interval to form a space surrounded by the two mold substrates and the film. An example of the space formation process will be explained using Figure 7. Figure 7 is a schematic diagram illustrating the space formation process.

[0222] First, as shown in Figure 7, a lens casting polymerization mold 110 is prepared. For example, a first mold substrate 111 for forming a convex surface and a second mold substrate 112 for forming a concave surface are prepared, both made of glass. The outer diameters of the mold substrates 111 and 112 may be the same as the finished outer diameter of the plastic lens. With the mold substrates 111 and 112 positioned opposite each other at a predetermined distance, a film (e.g., adhesive tape) 113 is wrapped around the outer circumferential surface of the mold substrates 111 and 112 slightly more than one full turn, fixing the mold substrates 111 and 112 with the adhesive tape and closing the gap between the mold substrates 111 and 112. This forms a space (i.e., a cavity 114 for forming the lens) surrounded by the two mold substrates and the film. The film 113 may be a heat-release or re-peelable adhesive tape.

[0223] In the manufacturing method of the optical component of the third embodiment, a mold is used. In the third embodiment, the mold (also referred to as a mold for manufacturing optical components) is preferably a mold for manufacturing optical components by attaching a film to the outer circumferential surfaces of two mold substrates arranged opposite each other at a predetermined interval to form a space surrounded by the two mold substrates and the film, placing a polymerizable composition in the space, and curing the polymerizable composition to obtain a cured product. In the third embodiment, the mold preferably has a main surface diameter of approximately 60 cm to 80 cm. As described above, when using the manufacturing method for optical members of the third embodiment, an optical member with a smooth outer surface can be manufactured without polishing, or with minimal polishing. Therefore, the approximate diameter of the main surface of the mold can be reduced by eliminating the need for polishing.

[0224] <film> The method for manufacturing the optical component of the third embodiment uses the film of the third embodiment (also referred to as the film for manufacturing optical components). The film in the third embodiment is preferably a film for manufacturing optical components, which is used to manufacture optical components by attaching the film to the outer circumferential surfaces of two mold substrates arranged opposite each other at a predetermined interval to form a space surrounded by the two mold substrates and the film, placing a polymerizable composition in the space, and curing the polymerizable composition in 10 hours or less to obtain a cured product. The film in the third embodiment (also referred to as a film for manufacturing optical components) preferably includes at least a base layer and an adhesive layer.

[0225] [Heat resistance index test] The film in the third embodiment is a film that peels off completely from the glass when it is attached to the glass and subjected to a heat resistance index test at 85°C. The static adhesive strength of a film can be measured by a heat resistance index test. The film in the third embodiment is such that when it is attached to glass and subjected to a heat resistance index test at 85°C, it peels off the glass completely, thereby suppressing static adhesive strength. The film in the third embodiment is a film with relatively weak static adhesive strength. This allows the film to move along the contact surface with the mold substrate when the polymerizable composition is cured and shrinks during the curing process. As a result, phenomena such as indentation or unevenness of the contact surface between the film and the polymerizable composition can be suppressed.

[0226] The specific method of the heat resistance index test is as follows. (Method) At room temperature, among the exposed surfaces of the adhesive layer of the film with a width of 25 mm ± 0.5 mm and a length of 80 mm ± 0.5 mm, an area of 625 mm 2 ± 25 mm 2 of the portion is adhered to a glass plate and crimped under a load of 1 kg / cm 2 . Then, a 1 kg weight is attached to the end of the folded portion of the film that is not adhered to the glass plate, and the glass plate is installed in a constant temperature bath at 85°C so that it is in the vertical direction. Thirty minutes after being placed in the constant temperature bath, the position of the upper end of the tape is measured, and the moving distance (mm) from the position immediately after attaching the 1 kg weight is calculated as the heat resistance index.

[0227] "When the heat resistance index test is performed by attaching to glass and it completely peels off from the glass" means that when the above heat resistance index test is performed, the film adhered to the glass plate separates from the glass plate within 30 minutes after being placed in the constant temperature bath, and there is no portion adhered to the glass plate.

[0228] The film in the third embodiment preferably has a heat resistance index of 0.4 mm or less, more preferably 0.3 mm or less, when the heat resistance index test is performed at 22°C by attaching to glass. By satisfying the above range of the heat resistance index, the film can firmly fix the mold substrate. Also, leakage of the polymerizable composition from the space can be suppressed when injecting the polymerizable composition. The film in the third embodiment may have a heat resistance index of 0 or more when the heat resistance index test is performed at 22°C.

[0229] 〔Heat distortion temperature〕 The film in the third embodiment preferably has a heat distortion temperature of 70°C or higher, and also preferably has a heat distortion temperature not lower than the maximum temperature of the mold in the curing process. By having a thermal distortion temperature of 70°C or higher, it is possible to manufacture optical components with a smooth outer surface. From the same viewpoint as above, it is preferable that the heat distortion temperature be 80°C or higher, more preferably 90°C or higher, even more preferably 120°C or higher, and particularly preferably 150°C or higher. The heat distortion temperature may be 500°C or lower, or 400°C or lower.

[0230] The heat distortion temperature was determined in accordance with ASTM-D648-56, using a heat distortion temperature measuring device, under a load of 4.6 kgf·cm. 2 Measured at [location / location].

[0231] In the third embodiment, it is preferable that the film exhibits a glass ball tack test at 80°C, with the glass ball traveling 200 mm or less. The dynamic adhesive strength of a film can be measured using a glass ball tack test. The film in the third embodiment exhibits excellent dynamic adhesion, as evidenced by the fact that the distance the glass ball travels is 200 mm or less when a glass ball tack test is performed at 80°C. As a result, the film in the third embodiment can fix the molded substrate more effectively.

[0232] In the third embodiment, the glass ball tack test is performed using a ball tack tester in accordance with JIS-Z0237. First, prepare a board with the film on its surface. Tilt the prepared board at a 30° angle so that the adhesive side of the film is facing upwards. Next, under a predetermined temperature, a measuring glass ball (4.65 ± 0.03 g) is rolled from a predetermined position on the film, and the distance traveled until the glass ball stops is measured.

[0233] In the third embodiment, it is preferable that the film exhibits a glass ball tack test at 25°C to 80°C, with the glass ball traveling 200 mm or less. In other words, when a glass ball tack test is performed at temperatures between 25°C and 80°C, it is preferable that the distance the glass ball travels is 200 mm or less in the entire temperature range from 25°C to 80°C. In the third embodiment, it is also preferable that the film exhibits a glass ball tack test at 120°C, with the glass ball traveling 200 mm or less.

[0234] In the third embodiment, when a glass ball tack test is performed at 25°C, 80°C, or 120°C, the film preferably has a glass ball migration distance of 10 mm or more, more preferably 20 mm or more, and even more preferably 30 mm or more. By keeping the glass ball's movement distance within the above range, the gap between mold substrates decreases at a suitable speed during curing, making leakage of the polymerizable composition less likely. Furthermore, the problem of the tape's adhesive layer remaining on the outer surface of the cured product (also known as adhesive residue) is less likely to occur.

[0235] The film in the third embodiment has a storage modulus of 1.0 × 10⁻⁶ at 80°C. 10 It is preferable that it be Pa or higher, 2.0 × 10 10 It is more preferable that it be Pa or higher, 3.0 × 10 10 It is even more preferable that the value be Pa or higher. The film in the third embodiment has a storage modulus of 10.0 × 10 at 80°C. 10 It is preferable that it is less than or equal to Pa, 8.0 × 10 10 It is more preferable that it be less than or equal to Pa, 6.0 × 10 10 It is even more preferable that it be Pa or less.

[0236] The following are specific examples of detailed conditions for the storage modulus measurement test. Measurement method: DMA single cantilever measurement • Test model: DMA8000 • Test temperature: 0~120℃ • Frequency: 1.0Hz • Heating rate: 3°C / min ·Measurement area: 1.2(cm 2 ) • Chuck spacing: 12.5mm

[0237] <Injection process> The injection step in the third embodiment is the step of injecting a polymerizable composition into the space. An example of the injection process will be explained using Figure 8. Figure 8 is a schematic diagram illustrating the injection process.

[0238] As shown in Figure 8, in the injection process, the adhesive tape 113 is peeled back to the extent that a gap is created in the cavity 114 through which the polymerizable composition can be injected. The polymerizable composition 120 is then injected into the cavity 114 through this gap, and the gap is sealed again with the adhesive tape 113.

[0239] The temperature during the injection process is preferably 30°C or lower, more preferably 27°C or lower, and even more preferably 25°C or lower. The temperature during the injection process is preferably 15°C or higher, more preferably 18°C ​​or higher, and even more preferably 20°C or higher.

[0240] <Polymerizable composition> The polymerizable composition in the third embodiment may be a polymerizable composition comprising two or more different monomers for optical materials and a polymerization catalyst.

[0241] The polymerizable composition in the third embodiment has a slope of the thickening curve (y=ae) at 25°C. bx It is preferable that ) is 0.4 or higher. By having a slope of 0.4 or higher on the thickening curve of the polymerizable composition at 25°C, the contact time between the relatively low-viscosity polymerizable composition and the film can be shortened. As a result, the amount of adhesive elution can be suppressed, and clouding, voids, and the like can be suppressed more effectively. From the same viewpoint as above, it is more preferable that the polymerizable composition has a slope of 0.5 or more on the thickening curve at 25°C, and even more preferable that it has a slope of 0.6 or more. The polymerizable composition in the third embodiment exhibits excellent handling properties because the slope of the thickening curve is 8.0 or less at 25°C. From the same viewpoint as described above, the polymerizable composition is more preferably such that the slope of the thickening curve at 25°C is 7.0 or less, and even more preferably 6.0 or less. y=ae bx The explanations for each symbol in this context are as follows: y: viscosity a: intercept e: Napier's number b: slope x: time

[0242] The slope of the thickening curve of a polymerizable composition at 25°C is measured by the following method. The polymerizable composition is placed in a water bath heated to 25°C and stirred. Then, the viscosity is measured at regular time intervals (e.g., every 5 minutes, every hour, etc.) using a B-type viscometer at 60 rpm. For the values ​​obtained from the measurements, a viscosity curvature curve (y=ae) is drawn with viscosity (unit: mPa·s) on the vertical axis and time (unit: h) on the horizontal axis. bx Create a graph and calculate the slope.

[0243] The polymerizable composition of the third embodiment comprises two or more different monomers for optical materials and a polymerization catalyst, wherein the content of the polymerization catalyst is preferably 0.010 parts by mass to 2.0 parts by mass per 100 parts by mass of the total of the two or more different monomers for optical materials, and the viscosity measured with a B-type viscometer at 25°C and 60 rpm is preferably 10 mPa·s to 1000 mPa·s.

[0244] (Monomers for optical materials) The polymerizable composition of the third embodiment may contain two or more different monomers for optical materials. The monomer used for optical materials can be any monomer used for optical purposes, and is not particularly limited. For example, a monomer used to manufacture an optical material having any of the following properties: Optical materials obtained using monomers for optical materials may have a total light transmittance of 10% or more. The total light transmittance of the above optical material may be measured in accordance with JIS K 7361-1 (1997). The optical material obtained using the monomer for optical materials has a haze (i.e., total haze) of 10% or less, preferably 1% or less, and more preferably 0.5% or less. The haze of the optical material is the value measured at 25°C using a haze measuring instrument [(Tokyo Denshoku Co., Ltd., TC-HIII DPK)] in accordance with JIS-K7105. The optical material obtained using the monomer for optical materials preferably has a refractive index of 1.58 or higher. The refractive index of the optical material obtained using the monomer for optical materials may also be 1.80 or lower, or 1.75 or lower. The refractive index of the optical material may be measured in accordance with JIS K7142 (2014).

[0245] The shape of the optical material obtained using the monomer for optical materials is not particularly limited and may be plate-shaped, cylindrical, rectangular, or the like.

[0246] Examples of monomers for optical materials include polymerizable monomers that polymerize when a polymerization catalyst, as described later, is used. Details regarding specific examples, preferred embodiments, and preferred content of monomers for optical materials in the third embodiment are the same as those regarding specific examples, preferred embodiments, and preferred content of monomers for optical materials in the first embodiment.

[0247] [Isocyanate compounds] Examples of isocyanate compounds include aliphatic isocyanate compounds, alicyclic isocyanate compounds, aromatic isocyanate compounds, and heterocyclic isocyanate compounds, which are used individually or in combination of two or more. These isocyanate compounds may include dimers, trimers, and prepolymers. Examples of these isocyanate compounds include those exemplified in International Publication No. 2011 / 055540. Furthermore, as isocyanate compounds, halogen-substituted compounds (e.g., chlorine-substituted compounds, bromine-substituted compounds, etc.), alkyl-substituted compounds, alkoxy-substituted compounds, carbodiimide-modified compounds, urea-modified compounds, and biuret-modified compounds of the above-mentioned compounds are also available. The above-mentioned compounds are used to create prepolymer-type modified products with nitro-substituted compounds, polyhydric alcohols, etc. The dimerization or trimmerization reaction products of the above-mentioned compounds can also be used. These compounds may be used individually or in combination of two or more.

[0248] The definitions of alicyclic isocyanate compounds, aromatic isocyanate compounds, heterocyclic isocyanate compounds, and aliphatic isocyanate compounds in the third embodiment are the same as the definitions of alicyclic isocyanate compounds, aromatic isocyanate compounds, heterocyclic isocyanate compounds, and aliphatic isocyanate compounds in the first embodiment.

[0249] The isocyanate compound preferably includes at least one selected from the group consisting of aliphatic isocyanate compounds, alicyclic isocyanate compounds, aromatic isocyanate compounds, and heterocyclic isocyanate compounds.

[0250] In the third embodiment, at least one of the monomers for the optical material may be an isocyanate compound having an aromatic ring. Specifically, examples of isocyanate compounds having an aromatic ring include aromatic isocyanate compounds, and more specifically, isocyanate compounds in which an isocyanate group is directly bonded to the aromatic ring, and isocyanate compounds in which an isocyanate group is bonded to the benzyl position of the aromatic ring. Monomers for optical materials may include isocyanate compounds other than those having an aromatic ring, i.e., isocyanate compounds that do not have an aromatic ring.

[0251] There are no particular restrictions on isocyanate compounds other than those having an aromatic ring, but examples include isocyanate compounds without an aromatic ring. When the monomer for optical materials includes isocyanate compounds without an aromatic ring and isocyanate compounds having an aromatic ring, it is preferable that the number of moles of isocyanate groups in the isocyanate compound without an aromatic ring is less than the number of moles of isocyanate groups in the isocyanate compound having an aromatic ring.

[0252] In the third embodiment, from the viewpoint of maintaining the quality of the optical material and shortening the manufacturing time of the optical material, the isocyanate compound preferably comprises at least one selected from the group consisting of isophorone diisocyanate, 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, m-xylylene diisocyanate, 2,4-tole diisocyanate, 2,6-tole diisocyanate, dicyclohexylmethane diisocyanate, 1,3-bis(isocyanatomethyl)cyclohexane, 1,4-bis(isocyanatomethyl)cyclohexane, 1,6-hexamethylene diisocyanate, and 1,5-pentamethylene diisocyanate. It is more preferable to include at least one selected from the group consisting of isophorone diisocyanate, 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, m-xylylene diisocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, dicyclohexylmethane diisocyanate, and 1,3-bis(isocyanatomethyl)cyclohexane. It is even more preferable to include at least one selected from the group consisting of 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, and 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane and m-xylylene diisocyanate.

[0253] [Active hydrogen compounds] Details regarding specific examples, preferred embodiments, and preferred content of the active hydrogen compound in the third embodiment are the same as those regarding specific examples, preferred embodiments, and preferred content of the active hydrogen compound in the first embodiment.

[0254] (Polythiol compounds having two or more mercapto groups) Details regarding specific examples, preferred embodiments, and preferred content of polythiol compounds having two or more mercapto groups in the third embodiment are the same as those regarding specific examples, preferred embodiments, and preferred content of polythiol compounds having two or more mercapto groups in the first embodiment.

[0255] (Polythiol compounds having three or more mercapto groups) Examples of active hydrogen compounds include polythiol compounds having three or more mercapto groups. In the polymerizable composition of the third embodiment, if it contains a polythiol compound having three or more mercapto groups as an active hydrogen compound, it is preferable from the viewpoint of promoting the polymerization reaction that it contains a compound (also referred to as compound (N1)) in which at least one of the three or more mercapto groups contained in the polythiol compound having three or more mercapto groups is substituted with a group represented by the following formula (N1).

[0256] [ka]

[0257] In formula (N1), * represents the bonding position.

[0258] In the polymerizable composition of the third embodiment, from the viewpoint of facilitating the adjustment of the polymerization reaction, when the peak area is measured by high-performance liquid chromatography, the peak area of ​​compound (N1) is preferably 3.0 or less, and more preferably 1.5 or less, relative to the peak area of ​​the polythiol compound having three or more mercapto groups (100). Furthermore, when measuring the peak area by high-performance liquid chromatography, it is preferable that the peak area of ​​compound (N1) be 0.01 or more relative to the peak area of ​​the polythiol compound having three or more mercapto groups (100), from the viewpoint of promoting the polymerization reaction. Furthermore, peak area obtained by high-performance liquid chromatography can be measured using the method described in paragraph 0146 of International Publication No. 2014 / 027665, etc.

[0259] (Hydroxythiol compounds containing one or more mercapto groups and one or more hydroxyl groups) Details regarding specific examples, preferred embodiments, and preferred content of hydroxythiol compounds having one or more mercapto groups and one or more hydroxyl groups in the third embodiment are the same as details regarding specific examples, preferred embodiments, and preferred content of hydroxythiol compounds having one or more mercapto groups and one or more hydroxyl groups in the first embodiment.

[0260] (Polyol compounds containing two or more hydroxyl groups) Details regarding specific examples, preferred embodiments, and preferred content of polyol compounds having two or more hydroxyl groups in the third embodiment are the same as those regarding specific examples, preferred embodiments, and preferred content of polyol compounds having two or more hydroxyl groups in the first embodiment.

[0261] (Amine compounds) Details of specific examples of amine compounds in the second embodiment, preferred embodiments, preferred content, (NCO group / (OH group+SH group)), viscosity Va, viscosity difference V, etc. are the same as details of specific examples of amine compounds in the first embodiment, preferred embodiments, preferred content, (NCO group / (OH group+SH group)), viscosity Va, viscosity difference V, etc.

[0262] <Polymerization catalyst> Details regarding specific examples, preferred embodiments, and preferred content of the polymerization catalyst in the third embodiment are the same as those regarding specific examples, preferred embodiments, and preferred content of the polymerization catalyst in the first embodiment.

[0263] (Basic catalyst) Details regarding specific examples of basic contact, preferred embodiments, preferred pKa, etc., in the third embodiment are the same as those regarding specific examples of basic contact, preferred embodiments, preferred pKa, etc., in the first embodiment.

[0264] As a basic catalyst, it is preferable that the pKa value is 1 or higher, more preferably 3 or higher, and even more preferably 4 or higher. As a basic catalyst, a pKa value of 9 or less is preferred, and a pKa value of 8 or less is more preferred.

[0265] (organometallic catalyst) Details regarding specific examples and preferred embodiments of organometallic catalysts in the third embodiment are the same as those regarding specific examples and preferred embodiments of organometallic catalysts in the first embodiment. By having a polymerization catalyst content of 0.010 parts by mass or more relative to a total of 100 parts by mass of the two or more different monomers for optical materials, the polymerization reaction can be effectively promoted, allowing for the acquisition of high-quality optical materials in a short time. Furthermore, by effectively promoting the polymerization reaction, the release properties when removing the cured product from the mold can be improved. From the above viewpoint, it is preferable that the content of the polymerization catalyst relative to 100 parts by mass of the total of the two or more different monomers for optical materials be 0.02 parts by mass or more, and more preferably 0.03 parts by mass or more.

[0266] By having the polymerization catalyst content be 2.0 parts by mass or less per 100 parts by mass of the total of the two or more different monomers for optical materials, for example, the handling properties when injecting the polymerizable composition into a mold can be improved. From the above viewpoint, the content of the polymerization catalyst relative to 100 parts by mass of the total of the two or more different monomers for optical materials is preferably 0.20 parts by mass or less, more preferably 0.10 parts by mass or less, and even more preferably 0.09 parts by mass or less. The content of the polymerization catalyst can be appropriately determined depending on the type of polymerization catalyst, the type and amount of monomers used (isocyanate compounds, active hydrogen compounds, other components, etc.), and the desired shape of the molded product.

[0267] The polymerization catalyst preferably satisfies condition 1 below. [Condition 1] -Ea / R is between -7100 and -2900. (Ea is the activation energy calculated by Arrhenius plot from the reaction rate constants of the two or more different monomers for optical materials at two or more different temperatures, and R is the gas constant (8.314 J / mol / K).)

[0268] The details of the significance of Condition 1 and the measurement method in the third embodiment are the same as those of the significance of Condition 1 and the measurement method in the second embodiment.

[0269] (Other additives) The polymerizable composition of the third embodiment may contain any additives. Optional additives include photochromic compounds, internal mold release agents, bluing agents, and ultraviolet absorbers. Details regarding specific examples of the photochromic compound, internal release agent, bluing agent, and ultraviolet absorber, as well as preferred embodiments, in the third embodiment are the same as those regarding specific examples of the photochromic compound, internal release agent, bluing agent, and ultraviolet absorber, as well as preferred embodiments, in the first embodiment.

[0270] (viscosity) The polymerizable composition of the third embodiment has a viscosity of 10 mPa·s or more, preferably 40 mPa·s or more, more preferably 70 mPa·s or more, even more preferably 80 mPa·s or more, particularly preferably 100 mPa·s or more, and even more preferably 120 mPa·s or more, as measured with a B-type viscometer at 25°C and 60 rpm, from the viewpoint of suppressing striation and suppressing the elution of the adhesive. The polymerizable composition of the third embodiment has a viscosity of 1000 mPa·s or less, preferably 700 mPa·s or less, and more preferably 400 mPa·s or less, as measured with a B-type viscometer at 25°C and 60 rpm, from the viewpoint of maintaining good handling when molding the optical material into a desired shape.

[0271] The viscosity of the polymerizable composition in the third embodiment may be adjusted depending on the intended use of the resulting cured product. For example, when obtaining a cured product using a mold for positive lenses, the edge (or injection port) is narrow (e.g., 1 mm to 3 mm), so from the viewpoint of suppressing striations, the polymerizable composition of the third embodiment preferably has a viscosity of 10 mPa·s to 100 mPa·s. On the other hand, when obtaining a cured product using a mold for ordinary lenses other than plus lenses, the edge (i.e., the injection port) is wide (for example, 5 mm to 15 mm), so the polymerizable composition of the third embodiment preferably has a viscosity of 10 mPa·s to 1000 mPa·s, and more preferably 100 mPa·s to 1000 mPa·s, from the viewpoint of suppressing striations.

[0272] By increasing the viscosity of the polymerizable composition, when heat is applied to the composition from the outside, thermal convection due to the temperature difference between the inside and outside of the composition can be suppressed, thereby reducing striations caused by thermal convection. However, if the amount of catalyst is insufficient, the viscosity increase rate during polymerization will not be sufficient, preventing the viscosity from becoming high enough to suppress thermal convection, and thus preventing a rapid increase in temperature in a short time. Furthermore, the time required to complete polymerization will also be longer. On the other hand, in the third embodiment, by considering the reactivity of the isocyanate compound and increasing the amount of catalyst to an optimal range, the viscosity of the entire composition can be increased more rapidly. This suppresses uneven polymerization and prevents thermal convection caused by a rapid temperature rise, allowing polymerization to proceed in a short time.

[0273] In the polymerizable composition of the third embodiment, from the viewpoint of suppressing striations and suppressing the elution of adhesives, the viscosity measured with a B-type viscometer at 40°C and 60 rpm when the temperature of the polymerizable composition reaches 40°C after the start of polymerization is preferably 100 mPa·s or more, more preferably 200 mPa·s or more, and even more preferably 500 mPa·s or more. In the third embodiment, from the viewpoint of maintaining good handling when injecting the polymerizable composition, the viscosity measured with a B-type viscometer at 40°C and 60 rpm when the temperature of the polymerizable composition reaches 40°C after the start of polymerization is preferably 2000 mPa·s or less, and more preferably 1500 mPa·s or less.

[0274] The polymerizable composition of the third embodiment preferably comprises two or more different monomers for optical materials, a polymerization catalyst, and a prepolymer which is a polymer of two or more different monomers for optical materials and has polymerizable functional groups. A prepolymer is a polymer of two or more different monomers used for optical materials, and is a polymer that has polymerizable functional groups. A cured product obtained by polymerizing a prepolymer with two or more different monomers for optical materials can be used as an optical material. Examples of prepolymers include polymers in which two of the optical material monomers are not polymerized in an equivalent ratio of 1:1, and polymers in which two of the optical material monomers are polymerized in an unbalanced equivalent ratio. The polymerizable functional group mentioned above is a functional group that can polymerize with other polymerizable functional groups, and specifically refers to functional groups having active hydrogen, such as isocyanate groups and mercapto groups, which will be described later. Polymerization at an equivalent ratio of 1:1 means, for example, when polymerizing an isocyanate compound and a polythiol compound, polymerizing in amounts such that the isocyanate group of the isocyanate compound and the mercapto group of the polythiol compound are in a molar ratio of 1:1.

[0275] <Curing process> The curing step in the third embodiment is a step of curing a polymerizable composition injected into a space to obtain a cured product. The method for manufacturing the optical component of the third embodiment, by including a curing step, allows the polymerizable composition to be polymerized and an optical material to be manufactured.

[0276] In the curing process, the curing time is preferably 10 hours or less. In particular, in the curing process of the third embodiment, when the curing time is 10 hours or less, the amount of adhesive elution tends to be significantly suppressed, and the above-mentioned clouding, voids, etc. can be suppressed more effectively.

[0277] In the third embodiment, the curing time refers to the time from when the temperature of the polymerizable composition reaches 30°C until the polymerizable composition is completely cured.

[0278] From the above perspective, a curing time of 7 hours or less is more preferable, and 5 hours or less is even more preferable.

[0279] From the viewpoint of the curability of the polymerizable composition, a curing time of 1 hour or more is preferable, and a curing time of 3 hours or more is more preferable.

[0280] The maximum curing temperature in the curing process is preferably 150°C or lower, more preferably 130°C or lower, even more preferably 100°C or lower, and particularly preferably 80°C or lower. The maximum curing temperature in the curing process is preferably 50°C or higher, more preferably 60°C or higher, and even more preferably 70°C or higher.

[0281] In the curing process, as the polymerizable composition cures, it is preferable that at least one of the two mold substrates moves on the contact surface with the film, and the distance between the mold substrates becomes smaller than the distance between the mold substrates in the space formation process. The above points will be explained in detail using Figure 9. Figure 9 is a schematic diagram illustrating the movement of the molded substrate during the curing process.

[0282] As shown in Figure 9, the curing process cures the polymerizable composition 120 in the cavity 114. The polymerizable composition 120 polymerizes, for example, by heating, active energy rays, etc., and polymerization shrinkage occurs. When this polymerization shrinkage occurs most severely, the holding power of the film (e.g., adhesive tape) 113 in holding the mold substrate decreases.

[0283] As a result of the decrease in the holding and adhesive strength of the film 113, the stress and self-weight associated with the polymerization shrinkage of the polymerizable composition 120 in the cavity 114 cause the upper mold substrate to slide down along the inner surface of the film 113 from the position fixed in the space formation process (shown by the dashed line in Figure 9) and approach the lower mold substrate. At this time, the amount of movement of the mold substrate is approximately equal to the amount of polymerization shrinkage of the polymerizable composition 120.

[0284] This allows the volume shrinkage of the polymerizable composition 120 to be absorbed by the movement of the mold substrates 111 and 112, preventing the film 113 from deforming. The sides of the resulting cured product (plastic lens) 130 have the shape of the undeformed film 113 transferred onto them, resulting in an aesthetically pleasing shape. Therefore, the outer diameters of the mold substrates 111 and 112 can be the same as the finished outer diameter of the plastic lens. This eliminates the waste of several millimeters of outer circumference that was previously removed during the polishing process. In the case of lenses with a thick outer circumference, this results in a reduction of more than 10% in polymerizable composition. Another advantage is that polishing is no longer required.

[0285] Conventionally, polymerization reactions were carried out by heating the polymerizable composition to initiate the polymerization reaction. The polymerizable composition in the third embodiment can also accelerate the polymerization reaction of the monomers for optical materials in the polymerizable composition by generating reaction heat (i.e., heat due to self-heating) in a short time. Therefore, in the method for manufacturing the optical component of the third embodiment, heating of the polymerizable composition is not necessarily required, but it may be done. That is, in the curing step of the third embodiment, the polymerizable composition can be cured by polymerization by allowing it to stand.

[0286] When promoting the polymerization reaction of monomers for optical materials in a polymerizable composition by generating reaction heat (i.e., heat due to self-heating) in a short time, the polymerization time can be shortened. Conventionally, in heat curing, it is common practice to gradually raise the temperature through heating and carry out the polymerization reaction over several hours to tens of hours in order to improve the quality of optical materials, and specifically, it generally takes about 20 to 48 hours. As mentioned above, when the polymerization reaction of monomers for optical materials in a polymerizable composition is accelerated by generating reaction heat (i.e., heat due to self-heating) in a short period of time, the curing time is often completed in a few hours to 20 hours.

[0287] In the curing process, it is preferable to cure the polymerizable composition by allowing the polymerizable composition injected into the space to stand in a closed system space. This makes it possible to obtain a cured product with excellent edge condition. Furthermore, by allowing the polymerizable composition to stand in a closed system space, the heat generated by the self-heating of the polymerizable composition can be prevented from being released to the outside. As a result, the heat generated by self-heating can be retained within the closed system space, which can promote the polymerization reaction more efficiently and allow optical materials to be manufactured in a shorter time. An example of a closed space is an insulated environment. An insulating environment refers to an environment in which heat is retained internally and heat conduction between the inside and outside is suppressed. An environment in which heat conduction between the inside and outside is suppressed means that when a polymerizable composition is left standing in a closed space, the heat conductivity between the inside and outside of the closed space prevents the polymerizable composition from curing. It means an environment that is at a level where it is possible to do so.

[0288] An insulated environment can be created, for example, by using insulating materials. In other words, by placing the polymerizable composition in an insulated container made of an insulating material, heat can be retained inside the insulated container, and heat conduction between the inside and outside can be suppressed.

[0289] The thermal conductivity of the insulating material is preferably 0.50 W / mK or less, more preferably 0.10 W / mK or less, and even more preferably 0.05 W / mK or less.

[0290] The density of the insulation material is 10 kg / m³. 3 Preferably, it should be 15 kg / m 3 It is more preferable that the amount be greater than or equal to 20 kg / m 3 It is even more preferable that the above conditions are met.

[0291] In the third embodiment, in the "thermal insulation" or "thermal insulation environment," it is preferable to heat the adiabatic reaction vessel to a constant temperature state (constant temperature reaction vessel) within a range that does not hinder the polymerization reaction due to the reaction heat of the polymerizable composition or excessively accelerate the polymerization reaction of the polymerizable composition by external heating. This allows the ambient temperature inside the reaction vessel (constant temperature reaction vessel) where the mold is placed to be maintained at a constant temperature or a warm temperature, depending on the temperature rise due to the self-heating of the monomer for optical materials, thereby promoting the polymerization reaction more effectively.

[0292] For example, an insulated reaction vessel or a constant-temperature reaction vessel, as described above, can be used as an insulated environment. For example, when a mold into which monomers have been injected is placed in a vacuum vessel which is an adiabatic reaction vessel, adiabatic polymerization in an adiabatic environment using an adiabatic reaction vessel (constant temperature reaction vessel) can be carried out by the following procedure. The inner surface of the vacuum container is covered with a material that has insulating and heat-retaining properties, such as urethane foam or cork, and the mold into which the monomer has been injected is wrapped in a material such as a cloth as needed. Then, the mold into which the monomer has been injected is left to stand in the vacuum container.

[0293] The curing step may also be a step in which the polymerizable composition is cured by allowing it to stand without external heating. As described above, in the third embodiment, heating of the polymerizable composition is not necessarily required. External heating may require the use of equipment, which can increase the economic burden. The manufacturing method for optical components of the third embodiment allows for the simple production of optical materials, thus reducing the economic burden.

[0294] The curing step is preferably a step in which the polymerizable composition is cured by allowing it to stand for 2 to 10 hours. According to conventional methods, polymerization reactions are generally carried out over several hours to tens of hours (for example, 20 to 48 hours) while gradually increasing the temperature through heating. If the polymerization reaction time is too short, the polymerizable composition may not fully harden, making it impossible to obtain an optical material, or the quality of the optical material may deteriorate. However, according to the third embodiment, optical materials can be manufactured in a short time while maintaining the quality of the resulting optical material. Specifically, optical materials can be manufactured by letting the polymerizable composition stand for 10 hours or less. From the above perspective, it is more preferable to allow the polymerizable composition to stand for 8 hours or less during the curing process. Furthermore, from the viewpoint of obtaining an optical material that has undergone polymerization and hardened well, it is preferable to allow the polymerizable composition to stand for 2 hours or more, and more preferably for 5 hours or more.

[0295] In the curing process, a microwave irradiation step may be provided, if necessary, in which the polymerizable composition is irradiated with microwaves for a predetermined time.

[0296] One embodiment of the curing process in the third embodiment is an embodiment that includes step b, which was described as one embodiment of the curing process in the first embodiment.

[0297] (cured product) The cured product of the third embodiment is a cured product of the polymerizable composition of the third embodiment. In the cured product of the third embodiment, from the viewpoint of reducing striations, when an amine-based catalyst is used as the polymerization catalyst, the amine content is preferably 0.03% by mass or more, more preferably 0.05% by mass or more, and even more preferably 0.07% by mass or more. Furthermore, from the viewpoint of improving the handling properties of the polymerizable composition for optical materials, the cured product of the third embodiment preferably has an amine content of 2.5% by mass or less, more preferably 2.0% by mass or less, and even more preferably 1.5% by mass or less. The amine content mentioned above is the amine content measured by gas chromatography-mass spectrometry from a dichloromethane composition obtained by dispersing the cured material in dichloromethane and ultrasonically extracting it.

[0298] In the cured product of the third embodiment, from the viewpoint of reducing striations, when an organotin-based catalyst is used, the tin content is preferably 0.05% by mass or more, more preferably 0.1% by mass or more, and even more preferably 0.2% by mass or more. Furthermore, from the viewpoint of improving the handling properties of the polymerizable composition for optical materials, the cured product of the third embodiment preferably has a tin content of 2.5% by mass or less, more preferably 2.0% by mass or less, and even more preferably 1.5% by mass or less.

[0299] The cured product of the third embodiment preferably has an amine content measured by gas chromatography-mass spectrometry of 0.03% by mass or more and 2.5% by mass or less.

[0300] The method for measuring the amine content in the cured product is as follows: 200 mg of the hardened material, powdered with a metal file, and 3 mL of dichloromethane are placed in a centrifuge tube (volume 10 mL). The mixture is ultrasonically extracted at room temperature for 10 minutes using an ultrasonic cleaner (IUCHI, US-4), and then centrifuged at 4000 rpm for 10 minutes using a centrifuge (KUBOTA, Benchtop Mini Centrifuge 2410). The supernatant is collected, the residue is dispersed again in 3 mL of dichloromethane, and the above ultrasonic extraction and centrifugation are performed, and the supernatant is collected (hereinafter also referred to as "residue extraction"). After performing the above residue extraction two more times, the obtained supernatant liquid was mixed to a total volume of 10 mL. Dichloromethane was added to achieve the desired result. The obtained 10 mL supernatant is filtered and analyzed by gas chromatography-mass spectrometry (GC-MS) (GC-MS instrument: Agilent 6890GC / 5973N MSD, column: CP-Sil 8 CB for Amine (0.25 mm ID × 30 m FT = 0.25 μm)) to obtain the peak area values ​​derived from amines. A calibration curve is prepared using the obtained amine-derived peak area values ​​and amine content to measure the amine content in the cured product.

[0301] The term "amine" refers to an amine compound that can be used as a polymerization catalyst, or an amine compound derived from the above-mentioned amine compound.

[0302] In optical applications where light transmittance is particularly required, the cured product of the third embodiment preferably has a devitrification degree of less than 50, and more preferably less than 35. Devitrification is measured by the following method. Apply a light source (for example, Hayashi Repic Luminar Ace) to the cured material in the dark. Light from LA-150A is transmitted. An image of the light transmitted through the cured material is captured by an image processing device (for example, an image processing device manufactured by Ube Information Systems Co., Ltd.), and grayscale processing is performed on the captured image. The degree of grayscale in the processed image is quantified for each pixel, and the value calculated as the average of the grayscale values ​​for each pixel is defined as the degree of detransparency.

[0303] In the third embodiment, it is preferable that the cured product does not have striations of 1.0 mm or longer within a radius of 15 mm from the center of the cured product, and it is more preferable that the cured product does not have striations of 1.0 mm or longer both within and outside a radius of 15 mm from the center of the cured product.

[0304] The cured product of the third embodiment may more specifically be a cured product of two or more different optical monomers, wherein at least one of the two or more different optical material monomers is an isocyanate compound that does not have an aromatic ring, and the cured product does not have striations of a length of 1.0 mm or more within a radius of 15 mm from the center of the cured product, and the amine content measured by gas chromatography-mass spectrometry is 0.03% by mass or more and 2.5% by mass or less.

[0305] The cured product of the third embodiment is a cured product of two or more different optical monomers, wherein there are no striations of a length of 1.0 mm or more within a radius of 15 mm from the center of the cured product. Preferably, the outer surface of the cured product is mirror-like, and the shape between the intersection of one main surface and the outer surface, and the intersection of the other main surface and the outer surface, is substantially straight.

[0306] In the third embodiment, it is preferable that the cured product includes projections substantially parallel to the outer circumferential surface at the intersection of one main surface and the outer circumferential surface, and at the intersection of the other main surface and the outer circumferential surface. When curing a polymerizable composition, small gaps (also called chamfers) are often provided in the mold at the intersection of the main surface of one mold and the film, and at the intersection of the main surface of the other mold and the film. The aforementioned protrusions are formed when the polymerizable composition enters the gaps and hardens.

[0307] The cured product of the third embodiment preferably contains at least one selected from the group consisting of urethane resin, thiourethane resin, and episulfide resin, and more preferably contains thiourethane resin.

[0308] <Annealing process> The method for manufacturing the optical component of the third embodiment may optionally include an annealing step of annealing the cured polymerizable composition. The annealing process is typically carried out at a temperature of 50-150°C, but is more preferably carried out at 90-140°C, and more preferably at 100-130°C.

[0309] <Optical components> The cured product in the third embodiment can be suitably used as an optical component. For example, the optical element in the third embodiment may have a thickness of 1 mm to 20 mm, or 4 mm to 16 mm.

[0310] <Applications of optical components> The optical component in the third embodiment can be used as a plastic lens, prism, optical fiber, information recording substrate, filter, light-emitting diode, etc. Among the above, the optical component in the third embodiment can be suitably used in plastic lenses, and more suitably used in plastic lenses for eyeglasses.

[0311] [Fourth Embodiment] ≪Method for manufacturing optical components≫ The manufacturing method for the optical component of the fourth embodiment includes a space formation step of attaching a film to the outer circumferential surfaces of two mold substrates arranged opposite each other at a predetermined interval to form a space surrounded by the two mold substrates and the film; an injection step of injecting a polymerizable composition into the space; and a curing step of curing the polymerizable composition injected into the space to obtain a cured product. The film has a heat resistance index of 1 mm or more when attached to glass and subjected to a heat resistance index test at 85°C (excluding cases where it completely peels off from the glass), and the film has a heat distortion temperature of 120°C or less. In addition, the curing time in the curing step is preferably 10 hours or less. In addition, the polymerizable composition preferably has a slope of 0.4 or more on the thickness curing curve at 25°C.

[0312] The method for manufacturing an optical member according to the fourth embodiment, by including the above configuration, can manufacture an optical member having a smooth outer surface. In the fourth embodiment, "the outer surface is smooth" means, for example, that the outer surface of the cured product is mirror-like, and the shape between the intersection of one main surface and the outer surface, and the intersection of the other main surface and the outer surface, is preferably a concave curve.

[0313] Furthermore, the method for manufacturing an optical component according to the fourth embodiment makes it possible to manufacture an optical component with a smooth outer surface without polishing, or with a small amount of polishing. During the curing process, when the polymerizable composition is cured and shrinks, the movement of the mold substrate on the contact surface with the film can be suppressed. As a result, the contact surface between the film and the polymerizable composition can be recessed inward.

[0314] Furthermore, the adhesive in the film may leach into the polymerizable composition. The adhesive that leaches into the polymerizable composition may cause clouding, voids, and other problems in the resulting cured product. The manufacturing method for the optical component of the fourth embodiment, by combining the above-described configurations, can effectively suppress the above-described opacity, voids, etc. In particular, in the curing process of the fourth embodiment, when the curing time is 10 hours or less, and the viscosity of the polymerizable composition is above a certain level, as will be described later, the amount of adhesive elution tends to be significantly suppressed, and the above-mentioned wrinkles, clouding, voids, etc. can be suppressed more effectively.

[0315] <Space formation process> Details of the specific and preferred modes of the space formation process in the fourth embodiment are the same as those of the specific and preferred modes of the space formation process in the third embodiment.

[0316] In the manufacturing method of the optical component of the fourth embodiment, a mold is used. Details of the specific and preferred forms of the mold in the fourth embodiment are the same as those of the specific and preferred forms of the mold in the third embodiment.

[0317] <film> The method for manufacturing the optical component of the fourth embodiment uses the film of the fourth embodiment (also referred to as the film for manufacturing optical components). The film in the fourth embodiment is preferably a film for manufacturing optical components, which is used to manufacture optical components by attaching the film to the outer circumferential surfaces of two mold substrates arranged opposite each other at a predetermined interval to form a space surrounded by the two mold substrates and the film, placing a polymerizable composition in the space, and curing the polymerizable composition in 10 hours or less to obtain a cured product. The film in the fourth embodiment (also referred to as a film for manufacturing optical components) preferably includes at least a base layer and an adhesive layer.

[0318] [Heat resistance index test] The film in the fourth embodiment has a heat resistance index of 1 mm or more when attached to glass and subjected to a heat resistance index test at 85°C (excluding cases where it completely peels off from the glass). The static adhesive strength of a film can be measured by a heat resistance index test. In the fourth embodiment, the film, when attached to glass and subjected to a heat resistance index test at 85°C, has a heat resistance index of 1 mm or more (excluding cases where it completely peels off from the glass), thereby allowing for good adjustment of static adhesive strength. In other words, during the curing process, when the polymerizable composition is cured and shrinks, the movement of the mold substrate on the contact surface with the film can be suppressed. As a result, the contact surface between the film and the polymerizable composition can be recessed inward.

[0319] From the above perspective, a heat resistance index of 2 mm or more is preferable, and 3 mm or more is more preferable. In the fourth embodiment, there is no particular limit to the upper limit of the heat resistance index of the film, as long as it does not completely peel off the glass when the film is attached to the glass and subjected to a heat resistance index test at 85°C. For example, the heat resistance index is preferably 15 mm or less, more preferably 10 mm or less, and even more preferably 7 mm or less. By satisfying the above range of heat resistance index, leakage of the polymerizable composition from the space can be suppressed when the polymerizable composition is injected. When the polymerizable composition is cured and at least one of the two mold substrates moves on the contact surface with the film, the mold substrate does not shift (i.e. It can suppress the deformation of space.

[0320] The specific method for the heat resistance index test in the fourth embodiment is the same as the specific method for the heat resistance index test in the third embodiment.

[0321] [Heat distortion temperature] Details regarding the preferred range and measurement method for the thermal distortion temperature of the film and the glass ball tack test in the fourth embodiment are the same as those regarding the preferred range and measurement method for the thermal distortion temperature of the film and the glass ball tack test in the third embodiment.

[0322] The film in the fourth embodiment has a storage modulus of 3.0 × 10 at 80°C. 10 It is preferable that it be Pa or higher, 5.0 × 10 10 It is more preferable that it be Pa or higher, 7.0 × 10 10 It is even more preferable that the value be Pa or higher. The film in the fourth embodiment has a storage modulus of 40.0 × 10 at 80°C. 10 It is preferable that it is less than or equal to Pa, 30.0 × 10 10 It is more preferable that it be less than or equal to Pa, 20.0 × 10 10 It is even more preferable that it be Pa or less.

[0323] The specific details of the storage modulus measurement test in the fourth embodiment are the same as the specific details of the storage modulus measurement test in the third embodiment.

[0324] [Adhesive strength] In the fourth embodiment, if the film includes at least a base layer and an adhesive layer, the adhesive strength of the adhesive layer is preferably 1.0 N / 10 mm to 10.0 N / 10 mm, more preferably 2.0 N / 10 mm to 7.0 N / 10 mm, and even more preferably 3.0 N / 10 mm to 5.0 N / 10 mm. Adhesion strength is measured in accordance with JIS Z 0237:2009.

[0325] <Injection process> Details of the specific and preferred embodiments of the injection process in the fourth embodiment are the same as those of the specific and preferred embodiments of the injection process in the third embodiment.

[0326] <Polymerizable composition> The polymerizable composition of the fourth embodiment may be a polymerizable composition comprising two or more different monomers for optical materials and a polymerization catalyst.

[0327] In the fourth embodiment, the polymerizable composition preferably has a slope of 0.4 or more on the thickening curve at 25°C. Details such as the preferred range of the slope of the thickening curve at 25°C for the polymerizable composition in the fourth embodiment, and the measurement method, are the same as those details such as the preferred range of the slope of the thickening curve at 25°C for the polymerizable composition in the third embodiment.

[0328] The polymerizable composition of the fourth embodiment comprises two or more different monomers for optical materials and a polymerization catalyst, wherein the content of the polymerization catalyst is preferably 0.010 parts by mass to 2.0 parts by mass per 100 parts by mass of the total of the two or more different monomers for optical materials, and the viscosity measured with a B-type viscometer at 25°C and 60 rpm is preferably 10 mPa·s to 1000 mPa·s.

[0329] (Monomers for optical materials) Details regarding specific examples, preferred embodiments, and preferred content of monomers for optical materials in the fourth embodiment are the same as those regarding specific examples, preferred embodiments, and preferred content of monomers for optical materials in the third embodiment.

[0330] [Isocyanate compounds] Details regarding specific examples, preferred embodiments, preferred content, and definitions of isocyanate compounds in the fourth embodiment are the same as those regarding specific examples, preferred embodiments, preferred content, and definitions of isocyanate compounds in the third embodiment.

[0331] The isocyanate compound preferably includes at least one selected from the group consisting of aliphatic isocyanate compounds, alicyclic isocyanate compounds, aromatic isocyanate compounds, and heterocyclic isocyanate compounds. In particular, from the viewpoint of suppressing polymerization reactivity to a certain extent and improving the edge condition, it is preferable that the isocyanate compound does not contain aromatic isocyanate compounds. Furthermore, if the isocyanate compound includes an aromatic isocyanate compound, from the same viewpoint as above, it is also preferable that the monomer for optical materials includes an aromatic isocyanate compound and a polythiol compound with four or more functions.

[0332] [Active hydrogen compounds] Details regarding specific examples, preferred embodiments, and preferred content of the active hydrogen compound in the fourth embodiment are the same as those regarding specific examples, preferred embodiments, and preferred content of the active hydrogen compound in the third embodiment.

[0333] (Polythiol compounds having two or more mercapto groups) Details regarding specific examples, preferred embodiments, and preferred content of polythiol compounds having two or more mercapto groups in the fourth embodiment are the same as those regarding specific examples, preferred embodiments, and preferred content of polythiol compounds having two or more mercapto groups in the third embodiment.

[0334] (Polythiol compounds having three or more mercapto groups) Details regarding specific examples, preferred embodiments, and preferred content of polythiol compounds having three or more mercapto groups in the fourth embodiment are the same as those regarding specific examples, preferred embodiments, and preferred content of polythiol compounds having three or more mercapto groups in the third embodiment.

[0335] (Hydroxythiol compounds containing one or more mercapto groups and one or more hydroxyl groups) Details regarding specific examples, preferred embodiments, and preferred content of hydroxythiol compounds having one or more mercapto groups and one or more hydroxyl groups in the fourth embodiment are the same as details regarding specific examples, preferred embodiments, and preferred content of hydroxythiol compounds having one or more mercapto groups and one or more hydroxyl groups in the third embodiment.

[0336] (Polyol compounds containing two or more hydroxyl groups) Details regarding specific examples, preferred embodiments, and preferred content of polyol compounds having two or more hydroxyl groups in the fourth embodiment are the same as those regarding specific examples, preferred embodiments, and preferred content of polyol compounds having two or more hydroxyl groups in the third embodiment.

[0337] (Amine compounds) Details of specific examples of amine compounds in the fourth embodiment, preferred embodiments, preferred content, (NCO group / (OH group + SH group)), viscosity Va, viscosity difference V, etc. are the same as details of specific examples of amine compounds in the third embodiment, preferred embodiments, preferred content, (NCO group / (OH group + SH group)), viscosity Va, viscosity difference V, etc.

[0338] <Polymerization catalyst> Details of the specific polymerization catalyst, preferred embodiment, preferred content, condition 1 (-Ea / R), etc. in the fourth embodiment are the same as those of the specific polymerization catalyst, preferred embodiment, preferred content, condition 1 (-Ea / R), etc. in the third embodiment.

[0339] (Basic catalyst) Details regarding specific examples of basic contact, preferred embodiments, preferred pKa, etc., in the fourth embodiment are the same as those regarding specific examples of basic contact, preferred embodiments, preferred pKa, etc., in the third embodiment.

[0340] (organometallic catalyst) Details regarding specific organometallic catalysts and preferred embodiments in the fourth embodiment are the same as those regarding specific organometallic catalysts and preferred embodiments in the third embodiment.

[0341] (Other additives) The polymerizable composition of the fourth embodiment may contain any additives. Optional additives include photochromic compounds, internal mold release agents, bluing agents, and ultraviolet absorbers. Details regarding specific examples of the photochromic compound, internal release agent, bluing agent, and ultraviolet absorber, as well as preferred embodiments, in the fourth embodiment are the same as those regarding specific examples of the photochromic compound, internal release agent, bluing agent, and ultraviolet absorber, as well as preferred embodiments, in the third embodiment.

[0342] (viscosity) Details such as the preferred viscosity range and adjustment method of the polymerizable composition in the fourth embodiment are the same as those details such as the preferred viscosity range and adjustment method of the polymerizable composition in the third embodiment.

[0343] <Curing process> Details of the specific mode, preferred mode, preferred time, preferred temperature, etc. of the curing process in the fourth embodiment are the same as details of the specific mode, preferred mode, preferred time, preferred temperature, etc. of the curing process in the third embodiment.

[0344] In the curing process, as the polymerizable composition hardens, it is preferable that the shape of the film between the intersection of one main surface and the outer peripheral surface, and between the intersection of the other main surface and the outer peripheral surface, becomes a concave curve. The above points will be explained in detail using Figure 10. Figure 10 is a schematic diagram illustrating the change in the shape of the film during the curing process.

[0345] As shown in Figure 10, the curing process cures the polymerizable composition 120 in the cavity 114. The polymerizable composition 120 polymerizes, for example, by heating or active energy rays, and polymerization shrinkage occurs. When this polymerization shrinkage occurs most severely, the shape-retaining force of the film (e.g., adhesive tape) 113 decreases.

[0346] As a result of the reduced shape retention of the film 113, the stress associated with the polymerization shrinkage of the polymerizable composition 120 in the cavity 114 causes the shape of the film between the intersection of one main surface and the outer surface, and between the intersection of the other main surface and the outer surface, to deform into a concave curve. In this case, the amount of deformation of the film is approximately equal to the amount of polymerization shrinkage of the polymerizable composition 120.

[0347] This allows the volume shrinkage of the polymerizable composition 120 to be absorbed by making the shape of the film between the intersection of one main surface and the outer surface, and between the intersection of the other main surface and the outer surface, a concave curve. The side surface of the resulting cured product 130 forms a concave curve. Therefore, the outer diameters of the mold substrates 111 and 112 can be the same as the finished outer diameter of the plastic lens. This eliminates the waste of several millimeters of outer circumference that was previously removed during the polishing process. In the case of lenses with a thick outer circumference, this results in a reduction of more than 10% in polymerizable composition. Another advantage is that polishing is no longer required.

[0348] Conventionally, polymerization reactions were carried out by heating the polymerizable composition to initiate the polymerization reaction. The polymerizable composition in the fourth embodiment can also accelerate the polymerization reaction of the monomers for optical materials in the polymerizable composition by generating reaction heat (i.e., heat due to self-heating) in a short time. The specific embodiments, preferred embodiments, definitions of closed-system spaces and thermal insulation environments, thermal conductivity and density of thermal insulation materials, polymerization time, etc., related to accelerating the polymerization reaction using the reaction heat associated with the polymerization reaction in the fourth embodiment are the same as the specific embodiments, preferred embodiments, definitions of closed-system spaces and thermal insulation environments, thermal conductivity and density of thermal insulation materials, polymerization time, etc., related to accelerating the polymerization reaction using the reaction heat associated with the polymerization reaction in the third embodiment.

[0349] One embodiment of the curing process in the fourth embodiment is an embodiment that includes step b, which was described as one embodiment of the curing process in the third embodiment.

[0350] (cured product) Details regarding the specific form of the cured product in the fourth embodiment, preferred form, preferred amine content, method for measuring the amine content, preferred tin content, devitrification degree, presence or absence of striations, etc., are the same as those regarding the specific form of the cured product, preferred form, preferred amine content, method for measuring the amine content, preferred tin content, devitrification degree, method for measuring the devitrification degree, presence or absence of striations, etc., in the third embodiment.

[0351] <Annealing process> The method for manufacturing the optical component of the fourth embodiment may optionally include an annealing step of annealing the cured polymerizable composition. The annealing process is typically carried out at a temperature of 50-150°C, but is preferably carried out at 90-140°C, and more preferably at 100-130°C.

[0352] <Optical components> The cured product in the fourth embodiment can be suitably used as an optical component. For example, the optical element in the fourth embodiment may have a thickness of 1 mm to 20 mm, or 4 mm to 16 mm.

[0353] <Applications of optical components> The optical component in the fourth embodiment can be used as a plastic lens, prism, optical fiber, information recording substrate, filter, light-emitting diode, etc. Among the above, the optical component in the fourth embodiment can be suitably used in plastic lenses, and more suitably in plastic lenses for eyeglasses. [Examples]

[0354] The following describes in detail one embodiment of the first embodiment, but the first embodiment is an implementation of these. This is not limited to the example. The method for measuring viscosity in the examples is the same as the method described above. The molded articles obtained in each example or comparative example were evaluated as follows.

[0355] (striae) The molded body was projected using an ultra-high pressure mercury lamp (light source model OPM-252HEG: manufactured by Ushio Inc.), and the transmitted image was visually observed and evaluated according to the following criteria. A: No pulse was observed, or pulse was not clearly observed. B: Although slight striations were observed, the product was generally acceptable. C: Numerous striations were observed, making the product unacceptable.

[0356] [Example 1] A mixture was prepared by charging 0.1 parts by mass of Mitsui Chemicals' internal release agent for MR [internal release agent], 1.5 parts by mass of Tinuvin 329 [ultraviolet absorber], and 40.6 parts by mass of 2,5(6)-bis(isocyanatomethyl)-bicyclo-[2.2.1]-heptane [monomer for optical materials]. This mixture was stirred at 25°C for 1 hour to completely dissolve the components. Then, 23.9 parts by mass of pentaerythritol tetrakis(3-mercaptopropionate) [monomer for optical materials] and 25.5 parts by mass of 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane [monomer for optical materials] were added to this mixture, and the mixture was stirred at 25°C for 5 minutes to obtain a homogeneous solution. Furthermore, 0.05 parts by mass of 3,5-lutidine [polymerization catalyst] (pKa value = 6.14) was added to the obtained homogeneous solution, and the mixture was stirred for 1 hour at 400 Pa and 25°C while degassing. The monomer for optical materials was polymerized while adjusting the viscosity to obtain a first mixture containing a prepolymer. The viscosity of the mixture containing the prepolymer is shown in Table 1.

[0357] A mixture was prepared by charging 10.0 parts by mass of 2,5(6)-bis(isocyanatomethyl)-bicyclo-[2.2.1]-heptane [monomer for optical materials] and 0.15 parts by mass of 3,5-lutidine [polymerization catalyst]. This mixture was stirred at 25°C for 15 minutes to obtain a second mixture. The first and second mixed solutions were then mixed at 20°C to obtain a polymerizable composition for optical materials.

[0358] The resulting polymerizable composition for optical materials was remixed in a stationary mixer and then transferred to a casting mold (i.e., a mold). The viscosity (also called casting viscosity) of the polymerizable composition for optical materials when it is delivered to the mold and cast was adjusted to the values ​​shown in Table 1. During the delivery of the polymerizable composition for optical materials, the polymerizable composition for optical materials was filtered through a 1 μm PTFE filter and injected at a rate of 10 g / second into the cavity of a mold type having a lens-making cavity with a set center thickness as described in Table 1, while being filtered through a 1 μm PTFE filter. The mold type consisted of a 78 mm diameter 4-curve or 6-curve glass mold (upper mold) and a 78 mm diameter 4-curve or 2-curve glass mold (lower mold). The cast material was placed in an insulated container at 25°C and allowed to stand for 2 hours to undergo adiabatic polymerization. After that, the cast material was removed from the insulated container and further heated and polymerized at 120°C for 1 hour. The hardened molded body was released from the mold, and then annealed at 120°C for 2 hours to obtain the molded body (lens).

[0359] [Examples 2-4] A molded article (lens) was obtained in the same manner as in Example 1, except that the amount of polymerization catalyst and stirring time of the first mixture in the prepolymerization step were changed to the values ​​shown in Table 1, and the casting viscosity of the polymerizable composition for optical materials was adjusted to the value shown in Table 1.

[0360] [Example 5] A mixture was prepared by charging 0.1 parts by mass of Mitsui Chemicals' internal release agent for MR [internal release agent], 1.5 parts by mass of Tinuvin 329 [ultraviolet absorber], and 50.6 parts by mass of 2,5(6)-bis(isocyanatomethyl)-bicyclo-[2.2.1]-heptane [monomer for optical materials]. This mixture was stirred at 25°C for 1 hour to completely dissolve the components. Then, 1.7 parts by mass of pentaerythritol tetrakis(3-mercaptopropionate) [monomer for optical materials] and 1.8 parts by mass of 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane [monomer for optical materials] into this mixture, and stirring at 25°C for 5 minutes was performed to obtain a homogeneous solution. Furthermore, 0.2 parts by mass of 3,5-lutidine [polymerization catalyst] was added to the obtained homogeneous solution and stirred at 40°C for 3 hours to polymerize the monomer for optical materials while adjusting the viscosity, thereby obtaining a mixture containing a prepolymer. The viscosity of the mixture containing the prepolymer is shown in Table 1. Subsequently, the mixture containing the prepolymer was degassed at 400 Pa and 25°C for 1 hour to obtain the first mixed solution. A mixture was prepared by charging 22.2 parts by mass of pentaerythritol tetrakis(3-mercaptopropionate) [monomer for optical materials] and 23.7 parts by mass of 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane [monomer for optical materials]. The resulting mixture was then degassed at 400 Pa and 25°C for 1 hour to obtain a second mixture. The first and second mixed solutions were then mixed at 20°C to obtain a polymerizable composition for optical materials. The obtained polymerizable composition for optical materials was poured into a casting mold using the same method as in Example 1, and the casting viscosity was adjusted to the values ​​shown in Table 1. The cast material was placed in an insulated container at 25°C and allowed to stand for 2 hours to undergo adiabatic polymerization. After that, the cast material was removed from the insulated container and further heated and polymerized at 120°C for 1 hour. The hardened molded body was released from the mold, and then annealed at 120°C for 2 hours to obtain the molded body (lens).

[0361] [Examples 6-7] A molded article (lens) was obtained in the same manner as in Example 5, except that the content of pentaerythritol tetrakis(3-mercaptopropionate) and 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctan in the prepolymerization step was changed to the values ​​shown in Table 1, and the casting viscosity of the polymerizable composition for optical materials was adjusted to the value shown in Table 1.

[0362] [Example 8] A molded body (lens) was obtained in the same manner as in Example 7, except that the cast material was placed in an insulated container at 25°C and left to stand for 3 hours to undergo adiabatic polymerization, and then the cast material was removed from the insulated container and demolded.

[0363] [Example 9] A molded body (lens) was obtained in the same manner as in Example 7, except that the cast material was heated from 30°C to 120°C over time, and thermal polymerization was carried out over 3 hours, without thermal polymerization of the cast material.

[0364] [Examples 10-11] A molded article (lens) was obtained in the same manner as in Example 5, except that the content of pentaerythritol tetrakis(3-mercaptopropionate) and 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctan in the prepolymerization step was changed to the values ​​shown in Table 1, and the casting viscosity of the polymerizable composition for optical materials was adjusted to the value shown in Table 1.

[0365] [Comparative Example 1] Mitsui Chemicals, Inc. Internal release agent for MR [Internal release agent] 0.1 parts by mass, Tinuvin 329 [ A mixture was prepared by charging 1.5 parts by mass of ultraviolet absorber and 40.6 parts by mass of 2,5(6)-bis(isocyanatomethyl)-bicyclo-[2.2.1]-heptane [monomer for optical materials]. This mixture was stirred at 25°C for 1 hour to completely dissolve the substances. Then, 23.9 parts by mass of pentaerythritol tetrakis(3-mercaptopropionate) [monomer for optical materials] and 25.5 parts by mass of 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane [monomer for optical materials] were added to this mixture, and the mixture was stirred at 25°C for 5 minutes to obtain a homogeneous solution. This solution was degassed at 400 Pa and 25°C for 1 hour to obtain the first mixture. 10.0 parts by mass of 2,5(6)-bis(isocyanatomethyl)-bicyclo-[2.2.1]-heptane [monomer for optical materials] and 0.035 parts by mass of dibutyltin dichloride (also known as DBC) [polymerization catalyst] were stirred at 25°C for 30 minutes to completely dissolve them and obtain a second mixture. The first and second mixtures were then mixed at 25°C to obtain a polymerizable composition for optical materials. The obtained polymerizable composition for optical materials was poured into a casting mold in the same manner as in Example 1. Without performing adiabatic polymerization on the cast object, it was heated from 10°C to 120°C over time, and thermal polymerization was carried out over 38 hours. Then, a molded body (lens) was obtained in the same manner as in Example 1.

[0366] [Comparative Example 2] The first mixture was obtained using the same method as in Comparative Example 1. 10.0 parts by mass of 2,5(6)-bis(isocyanatomethyl)-bicyclo-[2.2.1]-heptane [monomer for optical materials] and 0.2 parts by mass of 3,5-lutidine [polymerization catalyst] were stirred at 25°C for 30 minutes to completely dissolve them and obtain a second mixture. The first and second mixtures were mixed at 20°C to obtain a polymerizable composition for optical materials. The obtained polymerizable composition for optical materials was poured into a casting mold using the same method as in Example 1, and the casting viscosity was adjusted to the values ​​shown in Table 1. The cast material was placed in an insulated container at 25°C and allowed to stand for 2 hours to undergo adiabatic polymerization. After that, the cast material was removed from the insulated container and further heated and polymerized at 120°C for 1 hour. The hardened molded body was released from the mold, and then annealed at 120°C for 2 hours to obtain the molded body (lens).

[0367] [Table 1]

[0368] The monomer species listed in Tables 1 to 3 are as follows: a1: 2,5-Bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane and 2 Mixture with ,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane a2: m-xylylene diisocyanate a3: Dicyclohexylmethane diisocyanate a4: 1,3-Bis(isocyanatemethyl)cyclohexane b1:4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane b2: Pentaerythritol tetrakis (3-mercaptopropionate) b3: A mixture of 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, and 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane. b4: Pentaerythritol tetrakis (2-mercaptoacetate) b5: 2,5-Bis(mercaptomethyl)-1,4-Dithiane

[0369] As shown in Table 1, the preparation step involves preparing a total of 100 parts by mass of two or more different monomers for optical materials and 0.010 to 2.0 parts by mass of a polymerization catalyst. A prepolymerization step to obtain a mixture containing a prepolymer by mixing a portion of two or more different monomers for optical materials with at least a portion of a polymerization catalyst, and polymerizing at least a portion of the two or more different monomers for optical materials to obtain a prepolymer, A process for producing a polymerizable composition for optical materials, comprising adding the remainder of at least two different monomers for optical materials to a mixture containing a prepolymer, thereby obtaining a polymerizable composition for optical materials containing two or more different monomers for optical materials, a prepolymer, and a polymerization catalyst, A curing step to obtain an optical material which is a cured product of a polymerizable composition for optical materials by curing two or more different monomers for optical materials in a polymerizable composition for optical materials, The example using a method for manufacturing optical materials containing the material demonstrated that striations in the resulting optical material could be suppressed and the manufacturing time of the optical material could be shortened. On the other hand, Comparative Example 2, which did not undergo the prepolymerization process, was unable to suppress striations, and although Comparative Example 1 was able to suppress striations, the manufacturing time for the optical material was long at 38 hours, and the manufacturing time could not be shortened. Among the examples, Examples 2 to 4 and Examples 6 to 11, in which the viscosity of the polymerizable composition for optical materials during casting (i.e., casting viscosity) was 70 mPa·s or higher, were able to suppress striations more effectively.

[0370] [Example 12] A mixture was prepared by stirring 0.03 parts by mass of JP-506H (manufactured by Johoku Chemical Industry Co., Ltd.), an acidic phosphate ester, 1.5 parts by mass of Tinuvin 329 [ultraviolet absorber], and 40.7 parts by mass of m-xylylene diisocyanate [monomer for optical materials] at 25°C for 1 hour to completely dissolve them. Then, 49.3 parts by mass of a mixture of 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, and 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane [monomer for optical materials] was added to this mixture, and the mixture was stirred at 25°C for 5 minutes to obtain a homogeneous solution. Furthermore, 0.015 parts by mass of 3,5-lutidine [polymerization catalyst] (pKa value = 6.14) was added to the obtained homogeneous solution, and the mixture was stirred for 1 hour at 400 Pa and 25°C while degassing. The monomer for optical materials was polymerized while adjusting the viscosity to obtain a first mixture containing a prepolymer. The viscosity of the mixture containing the prepolymer is shown in Table 2. A mixture was prepared by charging 10 parts by mass of m-xylylene diisocyanate [monomer for optical materials] and 0.01 parts by mass of 3,5-lutidine [polymerization catalyst]. This mixture was stirred at 25°C for 15 minutes to obtain a second mixture. Then, the first and second mixtures are mixed at 20°C to obtain a polymerizable composition for optical materials. Ta. The obtained polymerizable composition for optical materials was poured into a casting mold using the same method as in Example 1, and the casting viscosity was adjusted to the values ​​shown in Table 2. The cast material was placed in an insulated container at 25°C and allowed to stand for 2 hours to undergo adiabatic polymerization. After that, the cast material was removed from the insulated container and further heated and polymerized at 120°C for 1 hour. Then, a molded body (lens) was obtained using the same method as in Example 1.

[0371] [Example 13] A molded article (lens) was obtained in the same manner as in Example 12, except that the amount of polymerization catalyst and stirring time of the first mixture in the prepolymerization step were changed to the values ​​shown in Table 2, and the casting viscosity of the polymerizable composition for optical materials was adjusted to the value shown in Table 2.

[0372] [Example 14] A mixture was prepared by charging 0.03 parts by mass of JP-506H (manufactured by Johoku Chemical Industry Co., Ltd.), an acidic phosphate ester, 1.5 parts by mass of Tinuvin 329 [ultraviolet absorber], and 50.7 parts by mass of m-xylylene diisocyanate [monomer for optical materials]. This mixture was stirred at 25°C for 1 hour to completely dissolve the substances. Then, 6.9 parts by mass of a mixture of 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, and 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane into this mixture and stirring at 25°C for 5 minutes to obtain a homogeneous solution. Furthermore, 0.025 parts by mass of 3,5-lutidine [polymerization catalyst] was added to the obtained homogeneous solution and stirred at 40°C for 3 hours to polymerize the monomer for optical materials while adjusting the viscosity, thereby obtaining a mixture containing a prepolymer. The viscosity of the mixture containing the prepolymer is shown in Table 2. Subsequently, the mixture containing the prepolymer was degassed at 400 Pa and 25°C for 1 hour to obtain the first mixed solution. A mixture of 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, and 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane was charged, and the mixture was degassed at 400 Pa and 25°C for 1 hour to obtain a second mixture. The first and second mixed solutions were then mixed at 20°C to obtain a polymerizable composition for optical materials. The obtained polymerizable composition for optical materials was poured into a casting mold using the same method as in Example 1, and the casting viscosity was adjusted to the values ​​shown in Table 2. The cast material was placed in an insulated container at 25°C and allowed to stand for 2 hours to undergo adiabatic polymerization. After that, the cast material was removed from the insulated container and further heated and polymerized at 120°C for 1 hour. The hardened molded body was released from the mold, and then annealed at 120°C for 2 hours to obtain the molded body (lens).

[0373] [Examples 15-19] A molded body (lens) was obtained in the same manner as in Example 14, except that the amount of polymerization catalyst in the prepolymerization step, the content of the mixture of 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, and 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, and the stirring time were changed to the values ​​shown in Table 2, and the casting viscosity of the polymerizable composition for optical materials was adjusted to the value shown in Table 2.

[0374] [Example 20] After placing the cast material in an insulated container at 25°C and allowing it to stand for 3 hours to undergo adiabatic polymerization, remove it from the insulated container. A molded body (lens) was obtained in the same manner as in Example 19, except that the cast material was removed and demolded.

[0375] [Example 21] A molded body (lens) was obtained in the same manner as in Example 19, except that the cast material was heated from 30°C to 120°C over time, and thermal polymerization was carried out over 3 hours, without thermal polymerization of the cast material.

[0376] [Comparative Example 3] A mixture was prepared by stirring 0.1 parts by mass of Mitsui Chemicals' internal mold release agent for MR, 1.5 parts by mass of Tinuvin 329 [ultraviolet absorber], and 40.7 parts by mass of m-xylylene diisocyanate [monomer for optical materials] at 25°C for 1 hour until completely dissolved. Then, 49.3 parts by mass of a mixture of 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, and 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane was added to this mixture and stirred at 25°C for 5 minutes to obtain a homogeneous solution. This solution was degassed at 400 Pa for 1 hour to obtain the first mixture. Furthermore, 10.0 parts by mass of m-xylylene diisocyanate [monomer for optical materials] and 0.008 parts by mass of dimethyltin dichloride (DMC) [polymerization catalyst] were stirred at 25°C for 10 minutes to completely dissolve them and obtain a second mixed solution. The first and second mixed solutions were then mixed at 20°C to obtain a polymerizable composition for optical materials. The obtained polymerizable composition for optical materials was poured into a casting mold using the same method as in Example 1, and the casting viscosity was adjusted to the values ​​shown in Table 2. The cast material was not subjected to adiabatic polymerization. Instead, it was heated from 20°C to 120°C over time, and thermal polymerization was carried out over 30 hours. Then, a molded body (lens) was obtained using the same method as in Example 1.

[0377] [Comparative Example 4] The first mixed solution was obtained in the same manner as in Comparative Example 3, except that 0.03 parts by mass of JP-506H (manufactured by Johoku Chemical Industry Co., Ltd.) was used instead of 0.1 parts by mass of Mitsui Chemicals' internal release agent for MR. 10.0 parts by mass of m-xylylene diisocyanate [monomer for optical materials] and 0.025 parts by mass of 3,5-lutidine [polymerization catalyst] were stirred at 25°C for 30 minutes to completely dissolve them and obtain a second mixed solution. The first and second mixtures were mixed at 20°C to obtain a polymerizable composition for optical materials. The obtained polymerizable composition for optical materials was poured into a casting mold using the same method as in Example 1, and the casting viscosity was adjusted to the values ​​shown in Table 2. The cast material was placed in an insulated container at 25°C and allowed to stand for 2 hours to undergo adiabatic polymerization. After that, the cast material was removed from the insulated container and further heated and polymerized at 120°C for 1 hour. The hardened molded body was released from the mold, and then annealed at 120°C for 2 hours to obtain the molded body (lens).

[0378] [Table 2]

[0379] As shown in Table 2, a total of 100 parts by mass of two or more different monomers for optical materials and 0. A preparation step to prepare 0.10 to 2.0 parts by mass of polymerization catalyst, A prepolymerization step to obtain a mixture containing a prepolymer by mixing a portion of two or more different monomers for optical materials with at least a portion of a polymerization catalyst, and polymerizing at least a portion of the two or more different monomers for optical materials to obtain a prepolymer, A process for producing a polymerizable composition for optical materials, comprising adding the remainder of at least two different monomers for optical materials to a mixture containing a prepolymer, thereby obtaining a polymerizable composition for optical materials containing two or more different monomers for optical materials, a prepolymer, and a polymerization catalyst, A curing step to obtain an optical material which is a cured product of a polymerizable composition for optical materials by curing two or more different monomers for optical materials in a polymerizable composition for optical materials, The example using a method for manufacturing optical materials containing the material demonstrated that striations in the resulting optical material could be suppressed and the manufacturing time of the optical material could be shortened. On the other hand, Comparative Example 4, which did not undergo a prepolymerization process, was unable to suppress striations, and Comparative Example 3, which contained less than 0.010 parts by mass of polymerization catalyst, had a long manufacturing time of 30 hours for the optical material, and the manufacturing time could not be shortened. Furthermore, Comparative Example 3 performed poorly in evaluating striations when manufacturing an optical material with a thickness of 15.6 mm (front: 6 curves, back: 2 curves). Among the examples, Examples 11-12 and 14-21, in which the viscosity of the polymerizable composition for optical materials during casting (i.e., casting viscosity) was 120 mPa·s or higher, were able to suppress striations more effectively.

[0380] [Example 22] A mixture was prepared by charging 0.05 parts by mass of JP-506H (manufactured by Johoku Chemical Industry Co., Ltd.), an acidic phosphate ester, 1.5 parts by mass of Tinuvin 329 [ultraviolet absorber], and 52 parts by mass of m-xylylene diisocyanate [monomer for optical materials]. This mixture was stirred at 25°C for 1 hour to completely dissolve the substances. Then, 7.7 parts by mass of 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane [monomer for optical materials] was charged into this mixture, and the mixture was stirred at 25°C for 5 minutes to obtain a homogeneous solution. Furthermore, 0.02 parts by mass of 3,5-lutidine [polymerization catalyst] was charged into the obtained homogeneous solution, and the mixture was stirred at 40°C for 3 hours to polymerize the monomer for optical materials while adjusting the viscosity, thereby obtaining a mixture containing a prepolymer. The viscosity of the mixture containing the prepolymer is shown in Table 3. Subsequently, the mixture containing the prepolymer was degassed at 400 Pa and 25°C for 1 hour to obtain the first mixed solution. 40.3 parts by mass of 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane were added, and the mixture was degassed at 400 Pa and 25°C for 1 hour to obtain a second mixture. The first and second mixed solutions were then mixed at 20°C to obtain a polymerizable composition for optical materials. The obtained polymerizable composition for optical materials was poured into a casting mold using the same method as in Example 1, and the casting viscosity was adjusted to the values ​​shown in Table 3. The cast material was placed in an insulated container at 25°C and allowed to stand for 2 hours to undergo adiabatic polymerization. After that, the cast material was removed from the insulated container and further heated and polymerized at 120°C for 1 hour. The hardened molded body was released from the mold, and then annealed at 120°C for 2 hours to obtain the molded body (lens).

[0381] [Examples 23-25] A molded article (lens) was obtained in the same manner as in Example 22, except that the content of 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctan in the prepolymerization step was changed to the value shown in Table 3, and the casting viscosity of the polymerizable composition for optical materials was adjusted to the value shown in Table 3.

[0382] [Example 26] A molded body (lens) was obtained in the same manner as in Example 25, except that the cast material was placed in an insulated container at 25°C and left to stand for 3 hours to undergo adiabatic polymerization, and then the cast material was removed from the insulated container and demolded.

[0383] [Example 27] A molded body (lens) was obtained in the same manner as in Example 25, except that the cast material was heated from 30°C to 120°C over time, and thermal polymerization was carried out over 3 hours, without thermal polymerization.

[0384] [Comparative Example 5] A mixture was prepared by stirring 0.1 parts by mass of Mitsui Chemicals' internal mold release agent for MR, 1.5 parts by mass of Tinuvin 329 [ultraviolet absorber], and 42.0 parts by mass of m-xylylene diisocyanate [monomer for optical materials] at 25°C for 1 hour until completely dissolved. Then, 48.0 parts by mass of 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane was added to this mixture and stirred at 25°C for 5 minutes to obtain a homogeneous solution. This solution was degassed at 400 Pa for 1 hour to obtain the first mixture. Furthermore, 10.0 parts by mass of m-xylylene diisocyanate [monomer for optical materials] and 0.01 parts by mass of dimethyltin dichloride (DMC) [polymerization catalyst] were stirred at 25°C for 10 minutes to completely dissolve them and obtain a second mixed solution. The first and second mixed solutions were then mixed at 20°C to obtain a polymerizable composition for optical materials. The obtained polymerizable composition for optical materials was poured into a casting mold using the same method as in Example 1, and the casting viscosity was adjusted to the values ​​shown in Table 3. The cast material was not subjected to adiabatic polymerization. Instead, it was heated from 20°C to 120°C over time, and thermal polymerization was carried out over 38 hours. Then, a molded body (lens) was obtained using the same method as in Example 1.

[0385] [Comparative Example 6] The first mixed solution was obtained in the same manner as in Comparative Example 5, except that 0.05 parts by mass of JP-506H (manufactured by Johoku Chemical Industry Co., Ltd.) was used instead of 0.1 parts by mass of Mitsui Chemicals' internal release agent for MR. 10.0 parts by mass of m-xylylene diisocyanate [monomer for optical materials] and 0.02 parts by mass of 3,5-lutidine [polymerization catalyst] were stirred at 25°C for 30 minutes to completely dissolve them and obtain a second mixed solution. The first and second mixtures were mixed at 20°C to obtain a polymerizable composition for optical materials. The obtained polymerizable composition for optical materials was poured into a casting mold using the same method as in Example 1, and the casting viscosity was adjusted to the values ​​shown in Table 3. The cast material was placed in an insulated container at 25°C and allowed to stand for 2 hours to undergo adiabatic polymerization. After that, the cast material was removed from the insulated container and further heated and polymerized at 120°C for 1 hour. The hardened molded body was released from the mold, and then annealed at 120°C for 2 hours to obtain the molded body (lens).

[0386] [Table 3]

[0387] As shown in Table 3, a total of 100 parts by mass of two or more different monomers for optical materials and 0. A preparation step to prepare 0.10 to 2.0 parts by mass of polymerization catalyst, A prepolymerization step to obtain a mixture containing a prepolymer by mixing a portion of two or more different monomers for optical materials with at least a portion of a polymerization catalyst, and polymerizing at least a portion of the two or more different monomers for optical materials to obtain a prepolymer, A process for producing a polymerizable composition for optical materials, comprising adding the remainder of at least two different monomers for optical materials to a mixture containing a prepolymer, thereby obtaining a polymerizable composition for optical materials containing two or more different monomers for optical materials, a prepolymer, and a polymerization catalyst, A curing step to obtain an optical material which is a cured product of a polymerizable composition for optical materials by curing two or more different monomers for optical materials in a polymerizable composition for optical materials, The example using a method for manufacturing optical materials containing the material demonstrated that striations in the resulting optical material could be suppressed and the manufacturing time of the optical material could be shortened. On the other hand, Comparative Example 6, which did not undergo a prepolymerization process, was unable to suppress striations, and in Comparative Example 5, the manufacturing time for the optical material was long at 38 hours, and the manufacturing time could not be shortened. Among the examples, Examples 23 to 27, in which the viscosity of the polymerizable composition for optical materials during casting (i.e., casting viscosity) was 230 mPa·s or higher, showed better suppression of striations.

[0388] [Example 28] A mixed solution was prepared by adding 58.9 parts by mass of dicyclohexylmethane diisocyanate [monomer for optical materials], 1.5 parts by mass of Tinuvin 329 [ultraviolet absorber], and 0.1 parts by mass of Mitsui Chemicals' MR internal release agent [internal release agent]. This mixture was stirred at 25°C for 1 hour to completely dissolve the substances. Then, 4.1 parts by mass of a mixture of 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, and 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane was added to this mixture, and the mixture was stirred at 25°C for 5 minutes to obtain a homogeneous solution. Furthermore, 1.5 parts by mass of 3,5-lutidine [polymerization catalyst] was added to the obtained homogeneous solution and stirred at 40°C for 4 hours to polymerize the monomer for optical materials while adjusting the viscosity, thereby obtaining a mixture containing a prepolymer. The viscosity of the mixture containing the prepolymer is shown in Table 4. Subsequently, the mixture containing the prepolymer was degassed at 400 Pa and 25°C for 1 hour to obtain the first mixed solution. A mixture of 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, and 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane was charged at 37.0 parts by mass, and the mixture was degassed at 400 Pa and 25°C for 1 hour to obtain a second mixture. The first and second mixed solutions were then mixed at 20°C to obtain a polymerizable composition for optical materials. The obtained polymerizable composition for optical materials was poured into a casting mold using the same method as in Example 1, and the casting viscosity was adjusted to the values ​​shown in Table 4. The cast material was placed in an insulated container at 25°C and allowed to stand for 3 hours to undergo adiabatic polymerization. After that, the cast material was removed from the insulated container and further heated and polymerized at 130°C for 2 hours. The hardened molded body was released from the mold, and then annealed at 120°C for 2 hours to obtain the molded body (lens).

[0389] [Table 4]

[0390] As shown in Table 4, the preparation step involves preparing a total of 100 parts by mass of two or more different monomers for optical materials and 0.010 to 2.0 parts by mass of a polymerization catalyst. A prepolymerization step to obtain a mixture containing a prepolymer by mixing a portion of two or more different monomers for optical materials with at least a portion of a polymerization catalyst, and polymerizing at least a portion of the two or more different monomers for optical materials to obtain a prepolymer, A process for producing a polymerizable composition for optical materials, comprising adding the remainder of at least two different monomers for optical materials to a mixture containing a prepolymer, thereby obtaining a polymerizable composition for optical materials containing two or more different monomers for optical materials, a prepolymer, and a polymerization catalyst, A curing step to obtain an optical material which is a cured product of a polymerizable composition for optical materials by curing two or more different monomers for optical materials in a polymerizable composition for optical materials, The example using a method for manufacturing optical materials containing the material demonstrated that striations in the resulting optical material could be suppressed and the manufacturing time of the optical material could be shortened.

[0391] [Example 29] A mixed solution was prepared by charging 48 parts by mass of 1,3-bis(isocyanatemethyl)cyclohexane [monomer for optical materials], 1.5 parts by mass of Tinuvin 329 [ultraviolet absorber], and 0.18 parts by mass of JP-506H (manufactured by Johoku Chemical Industry Co., Ltd.). This mixture was stirred at 25°C for 1 hour to completely dissolve the substances. Then, 4.0 parts by mass of pentaerythritol tetrakis(2-mercaptoacetate) and 3.9 parts by mass of 2,5-bis(mercaptomethyl)-1,4-dithiane were charged into this mixture, and the mixture was stirred at 25°C for 5 minutes to obtain a homogeneous solution. Furthermore, 0.1 parts by mass of 3,5-lutidine [polymerization catalyst] was charged into the obtained homogeneous solution, and the monomer for optical materials was polymerized while adjusting the viscosity by stirring at 40°C for 3 hours to obtain a mixture containing a prepolymer. The viscosity of the mixture containing the prepolymer is shown in Table 5. Subsequently, the mixture containing the prepolymer was degassed at 400 Pa and 25°C for 1 hour to obtain the first mixed solution. 22.7 parts by mass of pentaerythritol tetrakis(2-mercaptoacetate) and 22.3 parts by mass of 2,5-bis(mercaptomethyl)-1,4-dithiane were charged together, and the mixture was degassed at 400 Pa and 25°C for 1 hour to obtain a second mixture. The first and second mixed solutions were then mixed at 20°C to obtain a polymerizable composition for optical materials. The obtained polymerizable composition for optical materials was poured into a casting mold using the same method as in Example 1, and the casting viscosity was adjusted to the values ​​shown in Table 5. The cast material was placed in an insulated container at 25°C and allowed to stand for 2 hours to undergo adiabatic polymerization. After that, the cast material was removed from the insulated container and further heated and polymerized at 120°C for 1 hour. The hardened molded body was released from the mold, and then annealed at 120°C for 2 hours to obtain the molded body (lens).

[0392] [Table 5]

[0393] As shown in Table 5, a total of 100 parts by mass of two or more different monomers for optical materials and 0. A preparation step to prepare 0.10 to 2.0 parts by mass of polymerization catalyst, A prepolymerization step to obtain a mixture containing a prepolymer by mixing a portion of two or more different monomers for optical materials with at least a portion of a polymerization catalyst, and polymerizing at least a portion of the two or more different monomers for optical materials to obtain a prepolymer, A process for producing a polymerizable composition for optical materials, comprising adding the remainder of at least two different monomers for optical materials to a mixture containing a prepolymer, thereby obtaining a polymerizable composition for optical materials containing two or more different monomers for optical materials, a prepolymer, and a polymerization catalyst, A curing step to obtain an optical material which is a cured product of a polymerizable composition for optical materials by curing two or more different monomers for optical materials in a polymerizable composition for optical materials, The example using a method for manufacturing optical materials containing the material demonstrated that striations in the resulting optical material could be suppressed and the manufacturing time of the optical material could be shortened.

[0394] [Examples 101 to 103] In the prepolymerization step, isocyanates and thiols [monomers for optical materials] listed in Table 6 were used in the amounts listed in Table 6, 3,5-lutidine [polymerization catalyst] was used in the amount listed in Table 6, and MR internal release agent [release agent] was used in the amount listed in Table 6. The amount of monomers for optical materials added to the polymerizable composition for optical materials was adjusted to match the amount listed in Table 7, and the polymerization time and method were changed as shown in Table 6. Except for these changes, a molded article (lens) was obtained in the same manner as in Example 5. The evaluation of the striations is shown in Table 6.

[0395] [Examples 104-105] In the prepolymerization step, isocyanates and thiols [monomers for optical materials] listed in Table 6 were used in the amounts listed in Table 6, 3,5-lutidine [polymerization catalyst] was used in the amount listed in Table 6, JP-506H [release agent] was used in the amount listed in Table 6, and the amount of monomers for optical materials added to the polymerizable composition for optical materials was prepared as shown in Table 7. Except for changing the polymerization time and method as shown in Table 6, a molded article (lens) was obtained in the same manner as in Example 22. The evaluation of the striations is shown in Table 6.

[0396] [Example 106] A mixture was prepared by charging 1.5 parts by mass of Tinuvin 329 [ultraviolet absorber] and 48.9 parts by mass of m-xylylene diisocyanate [monomer for optical materials]. This mixture was stirred at 25°C for 1 hour to completely dissolve the substances. Then, 10.1 parts by mass of 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane [monomer for optical materials] was charged into this mixture, and it was stirred at 25°C for 5 minutes to obtain a homogeneous solution. Furthermore, 0.025 parts by mass of 3,5-lutidine [polymerization catalyst] was charged into the obtained homogeneous solution, and the monomer for optical materials was polymerized while adjusting the viscosity by stirring at 40°C for 1 hour to obtain a mixture containing a prepolymer. The viscosity of the mixture containing the prepolymer is shown in Table 6. Subsequently, the mixture containing the prepolymer was degassed at 400 Pa and 25°C for 1 hour, and 0.1 parts by mass of JP-506H [release agent] was added and stirred for 10 minutes to obtain the first mixed solution. A mixture was prepared by charging 37.9 parts by mass of 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane and 3.1 parts by mass of m-xylylene diisocyanate [monomer for optical materials]. This mixture was stirred at 25°C for 5 minutes to obtain a homogeneous solution. Furthermore, 0.005 parts by mass of 3,5-lutidine [polymerization catalyst] was charged into the obtained homogeneous solution and stirred at 40°C for 1 hour, thereby polymerizing the monomer for optical materials while adjusting the viscosity, to obtain a mixture containing a prepolymer. The viscosity of the mixture containing the prepolymer is shown in Table 6. This mixture was degassed at 400 Pa and 25°C for 1 hour to obtain a second mixture. The first and second mixed solutions were then mixed at 20°C to obtain a polymerizable composition for optical materials. The obtained polymerizable composition for optical materials was poured into a casting mold using the same method as in Example 1, and the casting viscosity was adjusted to the values ​​shown in Table 6. The cast material was placed in an insulated container at 25°C and allowed to stand for 2 hours to undergo adiabatic polymerization. After that, the cast material was removed from the insulated container and further heated and polymerized at 120°C for 1 hour. The hardened molded body was released from the mold, and then annealed at 120°C for 2 hours to obtain a molded body (lens). The evaluation of the striations is shown in Table 6.

[0397] [Examples 107-108] In the prepolymerization step, isocyanates and thiols [monomers for optical materials] listed in Table 6 were used in the amounts listed in Table 6, 3,5-lutidine [polymerization catalyst] was used in the amount listed in Table 6, JP-506H [release agent] was used in the amount listed in Table 6, and the amount of monomers for optical materials added to the polymerizable composition for optical materials was prepared as shown in Table 7. Except for changing the polymerization time and method as shown in Table 6, a molded article (lens) was obtained in the same manner as in Example 14. The evaluation of the striations is shown in Table 6.

[0398] [Table 6]

[0399] [Table 7]

[0400] Details regarding the descriptions of each item in Tables 6 and 7 are as follows: ·NBDI 2,5(6)-bis(isocyanatomethyl)-bicyclo-[2.2.1]-heptane ·XDI m-Xylylene diisocyanate PEMP Pentaerythritol Tetrakis (3-mercaptopropionate) GST 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane A mixture of FSH 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, and 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane.

[0401] The following describes in detail one embodiment of the second embodiment with reference to examples, but the second embodiment is not limited to these examples. The method for measuring viscosity in the examples is the same as the method described above. The molded articles obtained in each example or comparative example were evaluated as follows.

[0402] (striae) The molded body was projected using an ultra-high pressure mercury lamp (light source model OPM-252HEG: manufactured by Ushio Inc.), and the transmitted image was visually observed and evaluated according to the following criteria. A: No U-shaped striations were observed, or U-shaped striations were not clearly observed. B: Although slight U-shaped striations were observed, the product was generally acceptable. C: Clearly U-shaped striations were observed, which were unacceptable for a product.

[0403] [Examples 201-211] (Creation of a portrait) A mixture was prepared by charging 0.1 parts by mass of Mitsui Chemicals' internal release agent for MR [internal release agent], 1.5 parts by mass of Tinuvin 329 [ultraviolet absorber], and 50.6 parts by mass of 2,5(6)-bis(isocyanatomethyl)-bicyclo-[2.2.1]-heptane [monomer for optical materials]. This mixture was stirred at 25°C for 1 hour to completely dissolve the components. Then, 3.6 parts by mass of pentaerythritol tetrakis(3-mercaptopropionate) [monomer for optical materials] and 3.8 parts by mass of 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane [monomer for optical materials] into this mixture, and stirring at 25°C for 5 minutes was performed to obtain a homogeneous solution. Furthermore, 0.2 parts by mass of 3,5-lutidine [polymerization catalyst] (pKa value = 6.14, -Ea / R = -3397) was added to the obtained homogeneous solution and stirred at 40°C for 3 hours to polymerize the monomer for optical materials while adjusting the viscosity, thereby obtaining a mixture containing a prepolymer. Subsequently, the mixture containing the prepolymer was degassed at 400 Pa and 25°C for 1 hour to obtain the first raw material composition. The viscosity Va of the first raw material composition is shown in Table 8.

[0404] 20.3 parts by mass of pentaerythritol tetrakis(3-mercaptopropionate) [monomer for optical materials] and 21.7 parts by mass of 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane [monomer for optical materials] were charged and stirred at 25°C for 15 minutes to obtain a homogeneous solution. This mixture was degassed at 400 Pa and 25°C for 1 hour to obtain the second raw material composition. The viscosity Vb of the second raw material composition is shown in Table 8.

[0405] (Shearing and stirring of the composition) The first raw material composition was placed in the first tank, and the second raw material composition was placed in the second tank. Using a gear pump, each composition was delivered to a power mixer at the flow rates shown in Table 8. Next, using a power mixer at the rotation speeds shown in Table 8, shear force was applied to the first and second raw material compositions that had been delivered, and then they were passed through a capsule filter (manufactured by F-Tech Co., Ltd.) having the filtration accuracy shown in Table 8. The polymerizable composition for optical materials, after passing through the filter, was sent to a stirring tank and stirred in the tank at the rotational speeds listed in Table 8, thereby applying force to the polymerizable composition for optical materials in a direction approximately parallel to and opposite to the flow direction. At that time, back pressure was applied using nitrogen from the liquid surface side of the agitated tank at the pressures shown in Table 8. Subsequently, the polymerizable composition for optical materials was stirred in a static mixer having the inner diameter and number of elements described in Table 8, and then poured into a lens manufacturing mold with a diameter of 78 mm, 4 curves, and the set center thickness described in Table 8. The number of casting axes and the discharge volume of the castings are shown in Table 8.

[0406] (Curing of the composition) The polymerization reaction was carried out using one of the following methods. The molds after casting were placed in an insulated container at 25°C and allowed to stand for 2 hours to undergo adiabatic polymerization. After that, the cast material was removed from the insulated container and further heated and polymerized at 120°C for 1 hour. Using an oven, the mold after casting is heated from 30°C to 70°C over 1.5 hours, then heated from 70°C to 120°C over 0.5 hours, and then maintained at 120°C for 1 hour to perform heat polymerization.

[0407] After the polymerization reaction, the mold was allowed to cool naturally, the hardened molded body was released from the mold, and then the molded body (lens) was annealed at 120°C for 2 hours to obtain the molded body.

[0408] [Table 8]

[0409] In Table 8, "-" indicates that the corresponding operation was not performed or that the corresponding value does not exist.

[0410] As shown in Table 8, an example of a method for producing an optical material using a polymerizable composition for optical materials containing two or more different monomers for optical materials and a polymerization catalyst, comprising: a raw material composition preparation step of preparing a first raw material composition and a second raw material composition; a shearing step of applying shear force to the first raw material composition and the second raw material composition to produce a polymerizable composition for optical materials; a stirring step of applying stirring force to the polymerizable composition for optical materials; a casting step of pouring the polymerizable composition for optical materials into a mold after the stirring step; and a curing step of curing the polymerizable composition for optical materials by polymerizing two or more different monomers for optical materials in the polymerizable composition for optical materials in the mold, showed excellent evaluation of striations and was able to suppress U-shaped striations in the optical material.

[0411] The following describes a specific embodiment of the third embodiment with reference to examples, but the third embodiment is not limited to these examples. The method for measuring viscosity in the examples is the same as the method described above. The method for the heat resistance index test in the examples is the same as the method described above. The method for measuring the heat distortion temperature in the examples is the same as the method described above. The method for measuring the storage modulus in the examples is the same as the method described above. The method for the glass ball tack test in the examples is the same as the method described above. The method for measuring adhesive strength in the examples is the same as the method described above.

[0412] The following evaluations were performed on the cured products (i.e., lenses) obtained in each example or comparative example. [Edge smoothness] The smoothness of the outer surface of the cured material was visually confirmed. Case A was defined as having no irregularities of 1 mm or more in depth on the outer surface, and case B was defined as having irregularities of 1 mm or more in depth on the outer surface.

[0413] [Glue residue] We visually inspected the lenses and molds after curing to check for any remaining adhesive residue. Case A was defined as having no adhesive residue, case B as having adhesive residue that could be easily removed, and case C as having adhesive residue that was difficult to remove. Note that when adhesive residue was present, the outer surface appeared cloudy to the naked eye, while when there was no adhesive residue, the outer surface appeared mirror-like and almost transparent.

[0414] [Void] We visually inspected the cured material to see if voids had formed. Case A was defined as no voids occurring, and case B was defined as voids occurring.

[0415] [leak] Monomer leakage rate: "Monomer leakage" refers to the phenomenon of leakage from the mold in the oven after injection. The amount of monomer injected into the mold and the weight of the polymerized resin were measured, and the monomer leakage rate was defined and calculated using the following formula, representing the percentage of monomer that leaked from the mold in the oven after injection. Case A was defined as having a monomer leakage rate of 1% or less, and case B was defined as having a rate greater than 1%. Monomer injection amount = X (g) Resin mass after polymerization = Y (g) Monomer leakage amount = XY(g) Monomer leakage rate = (XY) / X × 100 (%)

[0416] [Development of resin burrs] "Resin burr formation" refers to the phenomenon where burrs form when the hardened material is released from a glass mold due to chipping of the material. Case A was defined as no burrs occurring, and case B was defined as burrs occurring.

[0417] [Cloudiness / elution] The cured product was visually inspected to see if any clouding or leaching of the adhesive had occurred. Cases where no clouding or leaching of adhesive was observed were classified as A, and cases where clouding or leaching of adhesive was observed were classified as B.

[0418] [protrusion] The intersection of one main surface and the outer peripheral surface in the cured product, and the intersection of the other main surface and the outer peripheral surface, were visually inspected to determine whether or not they contained protrusions substantially parallel to the outer peripheral surface. Cases where a protrusion was found were designated as A, and cases where no protrusion was found were designated as B.

[0419] <film> The film used in this embodiment is as follows: A: SLIONTEC #6261 (manufactured by Maxell Corporation) B: Mending Tape #810 (manufactured by 3M Japan Ltd.) C: SLIONTEC 6263-73 (manufactured by Maxell Corporation) Details of each film are shown in Table 9.

[0420] [Example 301] A mixture was prepared by charging 0.1 parts by mass of Mitsui Chemicals' internal release agent for MR [internal release agent], 1.5 parts by mass of Tinuvin 329 [ultraviolet absorber], and 50.6 parts by mass of 2,5(6)-bis(isocyanatomethyl)-bicyclo-[2.2.1]-heptane [monomer for optical materials]. This mixture was stirred at 25°C for 1 hour to completely dissolve the components. Then, 3.1 parts by mass of pentaerythritol tetrakis(3-mercaptopropionate) [monomer for optical materials] and 3.3 parts by mass of 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane [monomer for optical materials] were added to this mixture, and the mixture was stirred at 25°C for 5 minutes to obtain a homogeneous solution. Furthermore, the polymerization catalysts listed in Table 9 were added to the obtained homogeneous solution in the amounts listed in Table 9, and the mixture was stirred at 40°C for 3 hours to polymerize the monomers for optical materials while adjusting the viscosity, thereby obtaining a mixture containing a prepolymer. Subsequently, the mixture containing the prepolymer was degassed at 400 Pa and 25°C for 1 hour to obtain the first mixed solution. A mixture was prepared by charging 20.8 parts by mass of pentaerythritol tetrakis(3-mercaptopropionate) [monomer for optical materials] and 22.2 parts by mass of 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane [monomer for optical materials]. The resulting mixture was then degassed at 400 Pa and 25°C for 1 hour to obtain a second mixture. The first and second mixtures were then mixed at 20°C to obtain a polymerizable composition. The resulting polymerizable composition had a thickness curvature slope of 4.6822 at 25°C.

[0421] A casting mold was prepared by attaching the film described in Table 9 to the outer circumferential surfaces of two mold substrates arranged opposite each other at a predetermined distance, thereby forming a space surrounded by the two mold substrates and the film.

[0422] The resulting polymerizable composition is remixed in a stationary mixer while being processed in a 4-curve 80mm diameter container. The material was injected at a rate of 6 g / second into the aforementioned space, which has a central thickness of 10 mm and is composed of a glass mold (upper mold) and a glass mold with four curves and a diameter of 80 mm (lower mold). The viscosity (also called casting viscosity) of the polymerizable composition when it is delivered to the mold and cast was adjusted to the values ​​shown in Table 9.

[0423] Polymerization was carried out by heating the cast material in an oven at the temperatures and times listed in Table 9. The hardened material was released from the mold, and then annealed at 120°C for 2 hours to obtain a hardened product (lens).

[0424] [Example 302] A lens was obtained in the same manner as in Example 301, except that the cast material was placed in an insulated container at 25°C and allowed to stand for the curing time shown in Table 9 to carry out adiabatic polymerization. The maximum curing temperature is shown in Table 9.

[0425] [Example 303] A mixture was prepared by charging 0.05 parts by mass of JP-506H (manufactured by Johoku Chemical Industry Co., Ltd.), an acidic phosphate ester, 1.5 parts by mass of Tinuvin 329 [ultraviolet absorber], and 52.0 parts by mass of m-xylylene diisocyanate [monomer for optical materials]. The mixture was stirred at 25°C for 1 hour to completely dissolve it. Then, 12.0 parts by mass of 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane [monomer for optical materials] was added to this mixture, and it was stirred at 25°C for 5 minutes to obtain a homogeneous solution. Furthermore, the polymerization catalysts listed in Table 9 were added to the obtained homogeneous solution in the amounts listed in Table 9, and the mixture was stirred at 40°C for 3 hours to polymerize the monomer for optical materials while adjusting the viscosity, thereby obtaining a mixture containing a prepolymer. The viscosity of the mixture containing the prepolymer is shown in Table 9. Subsequently, the mixture containing the prepolymer was degassed at 400 Pa and 25°C for 1 hour to obtain the first mixed solution. 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane 36.0 mass After preparing the mixture, the second mixture was obtained by degassing it at 400 Pa and 25°C for 1 hour. The first and second mixtures were then mixed at 20°C to obtain a polymerizable composition. The resulting polymerizable composition had a slope of 1.8476 on the thickening curve at 25°C. The obtained polymerizable composition was then transferred to a casting mold using the same method as in Example 301, and the casting viscosity was adjusted to the values ​​shown in Table 9. Polymerization was carried out by heating the cast material in an oven at the temperature and time specified in Table 9. The hardened material was released from the mold, and then annealed at 120°C for 2 hours to obtain a hardened product (lens).

[0426] [Example 304] A lens was obtained in the same manner as in Example 303, except that the cast material was placed in an insulated container at 25°C and allowed to stand for the curing time shown in Table 9 to carry out adiabatic polymerization. The maximum curing temperature is shown in Table 9.

[0427] [Example 305] A lens was obtained in the same manner as in Example 303, except that 0.1 parts by mass of JP-506H and the polymerization catalyst were added in the total amount shown in Table 9. The maximum curing temperature is shown in Table 9. The resulting polymerizable composition had a slope of 0.9010 on the thickening curve at 25°C.

[0428] In Examples 301 and 302, the polymerizable composition had a viscosity of 164 mPa·s when measured with a B-type viscometer at 40°C and 60 rpm after the polymerization had started and the temperature of the polymerizable composition reached 40°C.

[0429] [Comparative Example 301] A lens was obtained in the same manner as in Example 301, except that the film was changed to the film listed in Table 9. The maximum curing temperature is shown in Table 9.

[0430] [Comparative Example 302] A lens was obtained in the same manner as in Example 302, except that the film was changed to the film listed in Table 9. The maximum curing temperature is shown in Table 9.

[0431] [Comparative Example 303] A mixed solution was prepared by charging 0.035 parts by mass of dibutyltin(II) dichloride [polymerization catalyst], 0.1 parts by mass of Mitsui Chemicals' internal release agent for MR [internal release agent], 1.5 parts by mass of Tinuvin 329 [ultraviolet absorber], and 50.6 parts by mass of 2,5(6)-bis(isocyanatomethyl)-bicyclo-[2.2.1]-heptane [monomer for optical materials]. This mixed solution was stirred at 25°C for 1 hour to completely dissolve the compounds. Then, 25.5 parts by mass of 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane and Pentaeri into this solution. 23.9 parts by mass of thritol tetrakis (3-mercaptopropionate) were added and stirred at 25°C for 30 minutes to prepare a homogeneous solution. The resulting solution (i.e., polymerizable composition) had a thickening curve slope of 0.2336 at 25°C. A casting mold was prepared using the film described in Table 9, in the same manner as described in Example 301. The obtained solution was degassed at 400 Pa for 1 hour, filtered through a 1 μm PTFE filter, and then transferred to a casting mold in the same manner as in Example 301, and the casting viscosity was adjusted to the values ​​shown in Table 9. Polymerization was carried out by heating the cast material in an oven at the temperature and time shown in Table 9. The cured material was released from the mold, and then annealed at 120°C for 2 hours to obtain a cured product (lens). The maximum curing temperature is shown in Table 9.

[0432] [Comparative Example 304] A lens was obtained in the same manner as in Example 301, except that the film was changed to one of the films listed in Table 9.

[0433] [Comparative Example 305] A lens was obtained in the same manner as in Example 302, except that the film was changed to one of the films listed in Table 9.

[0434] [Comparative Example 306] A lens was obtained in the same manner as in Comparative Example 303, except that the film was changed to the film listed in Table 9.

[0435] [Table 9]

[0436] As shown in Table 9, the process involves a space formation step of attaching a film to the outer circumferential surface of two mold substrates arranged opposite each other at a predetermined distance to form a space surrounded by the two mold substrates and the film, an injection step of injecting a polymerizable composition into the space, and the injection into the space An example of a method for manufacturing an optical component, comprising a curing step of curing the polymerizable composition to obtain a cured product, wherein the film is a film that peels completely off the glass when attached to glass and subjected to a heat resistance index test at 85°C, the film has a heat distortion temperature of 70°C or higher, and the curing time in the curing step is 10 hours or less, showed excellent evaluation of edge smoothness, adhesive residue, and protrusions. As a result, it was possible to manufacture an optical component with a smooth outer surface. In addition, the slope of the thickening curve in the example was 0.4 or higher at 25°C. Furthermore, the examples demonstrated excellent performance in evaluating voids, leaks, resin burr formation, and turbidity / elution. On the other hand, Comparative Examples 301 to 303, whose films did not have a thermal distortion temperature of 70°C or higher, performed poorly in the evaluation of edge smoothness, and were unable to manufacture optical components with smooth outer surfaces. Comparative Examples 301 to 303 also performed poorly in the evaluation of adhesive residue. Comparative Examples 304 to 306, which used films that did not completely peel off the glass when attached to glass and subjected to a heat resistance index test at 85°C, performed poorly in evaluating edge smoothness, and it was not possible to manufacture optical components with a smooth outer surface.

[0437] The following describes a specific embodiment of the fourth embodiment with reference to examples, but the fourth embodiment is not limited to these examples. The method for measuring viscosity in the examples is the same as the method described above. The method for the heat resistance index test in the examples is the same as the method described above. The method for measuring the heat distortion temperature in the examples is the same as the method described above. The method for measuring the storage modulus in the examples is the same as the method described above. The method for the glass ball tack test in the examples is the same as the method described above. The method for measuring adhesive strength in the examples is the same as the method described above.

[0438] The following evaluations were performed on the cured products (i.e., lenses) obtained in each example or comparative example. [Edge smoothness] The smoothness of the outer surface of the cured material was visually confirmed. In a cured product, if the shape between the intersection of one main surface and the outer surface and the intersection of the other main surface and the outer surface is a concave curve, and there are no irregularities of 1 mm or more in depth on the outer surface, then it is defined as A. In the cured product, if the shape between the intersection of one main surface and the outer surface, and the intersection of the other main surface and the outer surface, is not a concave curve, or if there are irregularities of 1 mm or more in depth on the outer surface, then it was defined as B.

[0439] [Void] We visually inspected the cured material to see if voids had formed. Case A was defined as no voids occurring, and case B was defined as voids occurring.

[0440] [leak] Monomer leakage rate: "Monomer leakage" refers to the phenomenon of leakage from the mold in the oven after injection. The amount of monomer injected into the mold and the weight of the polymerized resin were measured, and the monomer leakage rate was defined and calculated using the following formula, representing the percentage of monomer that leaked from the mold in the oven after injection. Case A was defined as having a monomer leakage rate of 1% or less, and case B was defined as having a rate greater than 1%. Monomer injection amount = X (g) Resin mass after polymerization = Y (g) Monomer leakage amount = XY(g) Monomer leakage rate = (XY) / X × 100 (%)

[0441] [Cloudiness / elution] The cured product was visually inspected to determine whether or not clouding or leaching of the adhesive had occurred. Cases where no clouding or leaching of adhesive was observed were classified as A, and cases where clouding or leaching of adhesive was observed were classified as B.

[0442] [protrusion] The intersection of one main surface and the outer peripheral surface in the cured product, and the intersection of the other main surface and the outer peripheral surface, were visually inspected to determine whether or not they contained protrusions substantially parallel to the outer peripheral surface. Cases where a protrusion was found were designated as A, and cases where no protrusion was found were designated as B.

[0443] <film> The film used in this embodiment is as follows: A: Cellotape (registered trademark) CT405AP-18 (manufactured by Nichiban Co., Ltd.) B: Cellotape (registered trademark) No. 252 (manufactured by Sekisui Chemical Co., Ltd.) © Cellotape (registered trademark) Tanosee (manufactured by Sekisui Chemical Co., Ltd.) D: Cellotape (registered trademark) NO29NEW (manufactured by Nitto Denko Corporation) E: Removable Tape #821 (Manufactured by 3M Japan Ltd.) Details of each film are shown in Table 10.

[0444] [Example 401] A mixture was prepared by charging 0.1 parts by mass of Mitsui Chemicals' internal release agent for MR [internal release agent], 1.5 parts by mass of Tinuvin 329 [ultraviolet absorber], and 50.6 parts by mass of 2,5(6)-bis(isocyan...

Claims

1. A method for producing an optical material using a total of 100 parts by mass of two or more different monomers for optical materials and 0.010 to 2.0 parts by mass of a polymerization catalyst as raw materials, A preparation step of preparing a total of 100 parts by mass of two or more different monomers for optical materials and 0.010 to 2.0 parts by mass of the polymerization catalyst, A prepolymerization step to obtain a mixture containing the prepolymer by mixing a portion of the two or more different monomers for optical materials and at least a portion of the polymerization catalyst, and polymerizing at least a portion of the two or more different monomers for optical materials to obtain a prepolymer, Includes, Furthermore, a process for producing a polymerizable composition for optical materials is provided, in which at least the remainder of the two or more different monomers for optical materials is added to the mixture containing the prepolymer to obtain a polymerizable composition for optical materials containing the two or more different monomers for optical materials, the prepolymer, and the polymerization catalyst. A curing step to obtain an optical material which is a cured product of the polymerizable composition for optical materials by curing two or more different monomers for optical materials in the polymerizable composition for optical materials, Includes, The prepolymerization step is a step of obtaining a mixture containing the prepolymer by mixing a portion of the two or more different monomers for optical materials with a portion or all of the polymerization catalyst, and polymerizing at least a portion of the two or more different monomers for optical materials to obtain a prepolymer. When the prepolymerization step involves mixing a portion of the two or more different monomers for optical materials and a portion of the polymerization catalyst, the polymerizable composition for optical materials manufacturing step involves adding at least the remainder of the two or more different monomers for optical materials and the remainder of the polymerization catalyst to the mixture containing the prepolymer to obtain a polymerizable composition for optical materials containing the two or more different monomers for optical materials, the prepolymer, and the polymerization catalyst. The two or more different monomers for optical materials include an isocyanate compound (A) and an active hydrogen compound (B) which is a polythiol compound having two or more mercapto groups. The polymerization catalyst comprises at least one selected from the group consisting of 3,5-lutidine, 2,4,6-collidine, triethylenediamine, N,N-dimethylethanolamine, and N-ethylmorpholine. A method for manufacturing optical materials.

2. A method for producing an optical material according to claim 1, wherein a portion of the two or more different monomers for optical materials comprises the entirety of one of the two or more different monomers for optical materials and a portion of the other monomers for optical materials other than the one monomer for optical materials.

3. The method for producing an optical material according to claim 1, wherein a portion of the polymerization catalyst is 5 to 80 parts by mass of 100 parts by mass of the polymerization catalyst.

4. A method for producing an optical material according to any one of claims 1 to 3, wherein a portion of the two or more different monomers for optical materials is 5 to 95 parts by mass out of 100 parts by mass of the two or more different monomers for optical materials.

5. A method for producing an optical material according to any one of claims 1 to 4, further comprising a viscosity adjustment step, which, after the prepolymerization step and before the polymerizable composition production step for optical materials, adjusts the viscosity of the mixture containing the prepolymer, measured with a B-type viscometer at 25°C and 60 rpm, to 30 mPa·s to 2000 mPa·s.

6. Furthermore, the method includes a second prepolymerization step of mixing the remainder of the two or more different monomers for optical materials with the remainder of the polymerization catalyst, and polymerizing at least a portion of the remainder of the two or more different monomers for optical materials to obtain a second prepolymer, thereby obtaining a mixture containing the second prepolymer. The process for producing the polymerizable composition for optical materials is a process of obtaining a polymerizable composition for optical materials containing the prepolymer, the second prepolymer, and the polymerization catalyst by adding a mixture containing the second prepolymer to a mixture containing the prepolymer. The method for producing an optical material according to claim 1, wherein the curing step is a step of curing the prepolymer and the second prepolymer in the polymerizable composition for optical materials to obtain an optical material which is a cured product of the polymerizable composition for optical materials.

7. The process, after the manufacturing step of the polymerizable composition for optical materials and before the curing step, further includes a liquid delivery step of delivering the polymerizable composition for optical materials to a casting mold, The method for producing an optical material according to any one of claims 1 to 6, wherein the liquid delivery step is a step of delivering the polymerizable composition for optical materials to a casting mold while remixing it in a stationary mixer.

8. A method for producing an optical material according to any one of claims 1 to 7, wherein the curing step includes a step of curing the polymerizable composition for optical materials by allowing the polymerizable composition for optical materials to stand.

9. A method for producing an optical material according to any one of claims 1 to 8, wherein the curing step includes a step of curing the polymerizable composition for optical materials by allowing it to stand in a closed system space.

10. A method for producing an optical material according to any one of claims 1 to 9, wherein the curing step includes a step of curing the polymerizable composition for optical materials by allowing it to stand without external heating.

11. A method for producing an optical material according to any one of claims 1 to 10, wherein the curing step includes a step of curing the polymerizable composition for optical materials by allowing it to stand for 2 to 10 hours.

12. The method for producing an optical material according to claim 1, wherein the isocyanate compound (A) comprises at least one of an alicyclic isocyanate compound and an aromatic isocyanate compound.

13. A method for producing an optical material using a polymerizable composition for optical materials containing two or more different monomers for optical materials and a polymerization catalyst, A raw material composition preparation step for preparing a first raw material composition and a second raw material composition, A shearing step to produce the polymerizable composition for optical materials by applying shear force to the first raw material composition and the second raw material composition, A stirring step in which stirring force is applied to the polymerizable composition for optical materials, After the stirring step, a casting step is performed in which the polymerizable composition for optical materials is poured into a mold. A curing step in which the polymerizable composition for optical materials is cured by polymerizing two or more different monomers for optical materials in the polymerizable composition for optical materials in the mold, Includes, A method for producing an optical material according to any one of claims 1 to 12, wherein at least one of the first raw material composition and the second raw material composition comprises a mixture containing the prepolymer.

14. The viscosity Va of the first raw material composition, measured with a B-type viscometer under the conditions of 25°C and 60 rpm, The method for producing an optical material according to claim 13, wherein the absolute value V of the difference between the viscosity Vb of the second raw material composition measured with a B-type viscometer at 25°C and 60 rpm is in the range of 20 mPa·s to 1500 mPa·s.

15. The method for producing an optical material according to claim 14, wherein the viscosity Va is in the range of 10 mPa·s to 2000 mPa·s.

16. The method for producing an optical material according to any one of claims 13 to 15, wherein the first raw material composition comprises at least one compound selected from the group consisting of polyisocyanate compounds, epoxy compounds, and epithio compounds.

17. A method for producing an optical material according to any one of claims 13 to 16, wherein the second raw material composition comprises at least one active hydrogen compound selected from the group consisting of a polythiol compound having two or more mercapto groups, a hydroxythiol compound containing one or more mercapto groups and one or more hydroxyl groups, a polyol compound containing two or more hydroxyl groups, and an amine compound.

18. A method for producing an optical material according to any one of claims 13 to 17, wherein the viscosity of the polymerizable composition for optical material in the casting step, measured with a B-type viscometer at 25°C and 60 rpm, is 10 mPa·s to 1000 mPa·s.

19. The polymerization catalyst is a method for producing an optical material according to any one of claims 13 to 18, satisfying the following condition 1. [Condition 1] -Ea / R is between -7100 and -2900. (Ea is the activation energy calculated by Arrhenius plot from the reaction rate constants of the two or more different monomers for optical materials at two or more different temperatures, and R is the gas constant (8.314 J / mol / K).)

20. The method for producing an optical material according to any one of claims 13 to 19, wherein the polymerization catalyst comprises at least one selected from the group consisting of a basic catalyst having a pKa value of 4 to 8 and an organometallic catalyst.

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