Polymerizable composition and method for producing same, resin, molded body, optical material, and lens

Abstract

This polymerizable composition contains: a polyiso(thio)cyanate compound (A); an active hydrogen compound (B); a nitrogen-containing compound (C) that is at least one of a nitrogen-containing aromatic heterocyclic compound and a tertiary amine compound; and water. The contained amount of the water with respect to the total amount of the polymerizable composition is 1900 mass ppm or less.

Description

Polymerizable composition and method for producing the same, resin, molded article, optical material, and lens

[0001] The present disclosure relates to a polymerizable composition and a method for producing the same, a resin, a molded article, an optical material, and a lens.

[0002] Polymerizable compositions containing an active hydrogen compound (e.g., a polythiol compound) and a polyiso(thio)cyanate compound are sometimes used as polymerizable compositions for producing resin optical materials (e.g., lenses). By polymerizing the monomers (i.e., the active hydrogen compound and the polyiso(thio)cyanate compound) in this polymerizable composition, an optical material containing a resin can be obtained. For example, Patent Document 1 discloses a polymerizable composition capable of producing a resin molded product with reduced opacity and striae, the polymerizable composition comprising: a bifunctional or higher iso(thio)cyanate compound; a bifunctional or higher active hydrogen compound (e.g., a polythiol compound); and a non-tin catalyst consisting of a compound having a specific chemical structure and a pKa of 1 to 9 (e.g., 2-methylpyrazine, β-picoline, γ-picoline, 2,6-lutidine, 3,5-lutidine, 3-chloropyridine, triallylamine, and trioctylamine).

[0003] Patent Document 1: International Publication No. 2018-079829

[0004] However, when the polymerizable composition described in Patent Document 1 containing the above-mentioned specific non-tin catalyst is used, although opacity and striae can be suppressed in the obtained resin, devitrification (i.e., devitrification evaluated by the devitrification degree) may not be suppressed. An object of one aspect of the present disclosure is to provide a polymerizable composition that is a composition containing a polyiso(thio)cyanate compound (A), an active hydrogen compound (B), a nitrogen-containing compound (C) that is at least one of a nitrogen-containing aromatic heterocyclic compound and a tertiary amine compound, and water, and that can produce a resin in which opacity, bubbles, and devitrification are suppressed, a method for producing the polymerizable composition, and a resin, molded article, and lens in which opacity, bubbles, and devitrification are suppressed.

[0005] Means for solving the above problems include the following aspects: <1> A polymerizable composition comprising: a polyiso(thio)cyanate compound (A), an active hydrogen compound (B), a nitrogen-containing compound (C) which is at least one of a nitrogen-containing aromatic heterocyclic compound and a tertiary amine compound, and water, wherein the water content is 1900 ppm by mass or less based on the total amount of the polymerizable composition.

[0006] <2> The polymerizable composition according to <1>, wherein the nitrogen-containing compound (C) includes at least one of a compound represented by the following formula (1) and a compound represented by the following formula (2):

[0007]

[0008] In formula (1), m R １ each independently 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; Q represents a carbon atom or a nitrogen atom; and m represents an integer of 0 to 5. ２ , R ３ , and R ４ R each independently represents a linear alkyl group having 3 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. ２ and R ３ may be bonded to each other to form a ring.

[0009] <3> The polymerizable composition according to <2>, wherein the compound represented by formula (1) is at least one selected from the group consisting of 2-methylpyrazine, pyridine, α-picoline, β-picoline, γ-picoline, 2,6-lutidine, 3,5-lutidine, 2,4,6-trimethylpyridine, 3-chloropyridine, 2-ethylpyridine, and 3-ethylpyridine, and the compound represented by formula (2) is at least one selected from the group consisting of triallylamine and trioctylamine. <4> The polymerizable composition according to any one of <1> to <3>, wherein the polyiso(thio)cyanate compound (A) includes at least one selected from the group consisting of pentamethylene diisocyanate, hexamethylene diisocyanate, xylylene diisocyanate, isophorone diisocyanate, bis(isocyanatomethyl)cyclohexane, bis(isocyanatocyclohexyl)methane, 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, tolylene diisocyanate, 4,4'-diphenylmethane diisocyanate, and phenylene diisocyanate. <5> The polymerizable composition according to any one of <1> to <4>, wherein the active hydrogen compound (B) is a polythiol compound (B1).<6> The polythiol compound (B1) is 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, 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, pentaerythritol tetrakis(3-mercaptopropionate), pentaerythritol tetrakis(2-mercaptoacetate), 2,5-bis(mercaptomethyl)-1,11-dimercaptopropionate, ... The polymerizable composition according to <5>, comprising at least one selected from the group consisting of 1,1,3,3-tetrakis(mercaptomethylthio)propane, 4,6-bis(mercaptomethylthio)-1,3-dithiane, 2-(2,2-bis(mercaptomethylthio)ethyl)-1,3-dithietane, 1,1,2,2-tetrakis(mercaptomethylthio)ethane, 3-mercaptomethyl-1,5-dimercapto-2,4-dithiapentane, and tris(mercaptomethylthio)methane. <7> The polymerizable composition according to any one of <1> to <6>, wherein the water content is 100 ppm by mass or more relative to the total amount of the polymerizable composition. <8> A method for producing the polymerizable composition according to any one of <1> to <6>, comprising a step of mixing a raw material composition (BX) containing the active hydrogen compound (B) and water, wherein the water content is 3800 ppm by mass or less based on the total amount of the raw material composition (BX), the polyiso(thio)cyanate compound (A), and the nitrogen-containing compound (C). <9> A resin that is a cured product of the polymerizable composition according to any one of <1> to <7>. <10> A molded product containing the resin according to <9>. <11> An optical material containing the resin according to <9>. <12> A lens containing the resin according to <9>.

[0010] According to one aspect of the present disclosure, there are provided a polymerizable composition that includes a polyiso(thio)cyanate compound (A), an active hydrogen compound (B), a nitrogen-containing compound (C) that is at least one of a nitrogen-containing aromatic heterocyclic compound and a tertiary amine compound, and water, and that can produce a resin in which opacity, bubbles, and devitrification are suppressed; a method for producing the polymerizable composition; and a resin, molded article, and lens in which opacity, bubbles, and devitrification are suppressed.

[0011] In the present disclosure, a numerical range expressed using "to" means a range that includes the numerical values ​​written before and after "to" as the lower and upper limits. In the present disclosure, when a composition contains multiple substances corresponding to each component, the amount of each component refers to the total amount of the multiple substances present in the composition, unless otherwise specified. In the numerical ranges described in stages in the present disclosure, the upper or lower limit described in one numerical range may be replaced with the upper or lower limit of another numerical range described in stages. Furthermore, in the numerical ranges described in the present disclosure, the upper or lower limit of that numerical range may be replaced with a value shown in the examples.

[0012] [Polymerizable Composition] The polymerizable composition of the present disclosure comprises: a polyiso(thio)cyanate compound (A); an active hydrogen compound (B); a nitrogen-containing compound (C) which is at least one of a nitrogen-containing aromatic heterocyclic compound and a tertiary amine compound; and water, wherein the water content is 1900 ppm by mass or less with respect to the total amount of the polymerizable composition.

[0013] The polymerizable composition of the present disclosure can produce a resin in which opacity, bubbles, and devitrification are suppressed. The effects of suppressing opacity and bubbles are achieved by the nitrogen-containing compound (C) as a curing catalyst. The effects of suppressing devitrification are achieved by controlling the water content to 1900 ppm by mass or less relative to the total amount of the polymerizable composition.

[0014] In particular, when a nitrogen-containing compound (C) is used as a curing catalyst, opacity and striae can be suppressed, but devitrification (i.e., devitrification evaluated by the devitrification degree) may not be suppressed. In this regard, in the polymerizable composition of the present disclosure, by setting the water content to 1900 ppm by mass or less relative to the total amount of the polymerizable composition, the effect of suppressing opacity and striae can be obtained while also suppressing devitrification.

[0015] <Polyiso(thio)cyanate Compound (A)> The polymerizable composition of the present disclosure contains at least one polyiso(thio)cyanate compound (A). The polyiso(thio)cyanate compound (A) is not particularly limited as long as it is a compound having at least two iso(thio)cyanate groups in one molecule. Specific examples of the polyiso(thio)cyanate compound (A) include: aliphatic polyisocyanate compounds such as tetramethylene diisocyanate, pentamethylene diisocyanate, hexamethylene diisocyanate, heptamethylene diisocyanate, octamethylene diisocyanate, 2,2,4-trimethylhexamethylene diisocyanate, 2,4,4-trimethylhexamethylene diisocyanate, lysine diisocyanate methyl ester, lysine triisocyanate, and xylylene diisocyanate; Alicyclic polyisocyanate compounds such as isophorone diisocyanate, bis(isocyanatomethyl)cyclohexane, bis(isocyanatocyclohexyl)methane, dicyclohexyldimethylmethane diisocyanate, 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, 3,8-bis(isocyanatomethyl)tricyclodecane, 3,9-bis(isocyanatomethyl)tricyclodecane, 4,8-bis(isocyanatomethyl)tricyclodecane, and 4,9-bis(isocyanatomethyl)tricyclodecane; aromatic polyisocyanate compounds such as tolylene diisocyanate, 4,4'-diphenylmethane diisocyanate, diphenyl sulfide-4,4'-diisocyanate, and phenylene diisocyanate; Heterocyclic polyisocyanate compounds such as 2,5-diisocyanatothiophene, 2,5-bis(isocyanatomethyl)thiophene, 2,5-diisocyanatotetrahydrothiophene, 2,5-bis(isocyanatomethyl)tetrahydrothiophene, 3,4-bis(isocyanatomethyl)tetrahydrothiophene, 2,5-diisocyanato-1,4-dithiane, 2,5-bis(isocyanatomethyl)-1,4-dithiane, 4,5-diisocyanato-1,3-dithiolane, and 4,5-bis(isocyanatomethyl)-1,3-dithiolane;Aliphatic polyisothiocyanate compounds such as hexamethylene diisothiocyanate, lysine diisothiocyanate methyl ester, lysine triisothiocyanate, and xylylene diisothiocyanate; alicyclic polyisothiocyanate compounds such as isophorone diisothiocyanate, bis(isothiocyanatomethyl)cyclohexane, bis(isothiocyanatocyclohexyl)methane, cyclohexane diisothiocyanate, methylcyclohexane diisothiocyanate, 2,5-bis(isothiocyanatomethyl)bicyclo-[2.2.1]-heptane, 2,6-bis(isothiocyanatomethyl)bicyclo-[2.2.1]-heptane, 3,8-bis(isothiocyanatomethyl)tricyclodecane, 3,9-bis(isothiocyanatomethyl)tricyclodecane, 4,8-bis(isothiocyanatomethyl)tricyclodecane, and 4,9-bis(isothiocyanatomethyl)tricyclodecane; Aromatic polyisothiocyanate compounds such as tolylene diisothiocyanate, 4,4'-diphenylmethane diisothiocyanate, and diphenyl disulfide-4,4'-diisothiocyanate; and sulfur-containing heterocyclic polyisothiocyanate compounds such as 2,5-diisothiocyanatothiophene, 2,5-bis(isothiocyanatomethyl)thiophene, 2,5-isothiocyanatotetrahydrothiophene, 2,5-bis(isothiocyanatomethyl)tetrahydrothiophene, 3,4-bis(isothiocyanatomethyl)tetrahydrothiophene, 2,5-diisothiocyanato-1,4-dithiane, 2,5-bis(isothiocyanatomethyl)-1,4-dithiane, 4,5-diisothiocyanato-1,3-dithiolane, and 4,5-bis(isothiocyanatomethyl)-1,3-dithiolane. The polyiso(thio)cyanate compound may contain at least one selected from these compounds;

[0016] Furthermore, as the polyiso(thio)cyanate compound (A), halogen-substituted products such as chlorine-substituted products and bromine-substituted products, alkyl-substituted products, alkoxy-substituted products, nitro-substituted products, prepolymer-type modified products with polyhydric alcohols, carbodiimide-modified products, urea-modified products, biuret-modified products, dimerization or trimerization reaction products, etc. can also be used.

[0017] The polyiso(thio)cyanate compound (A) preferably contains a polyisocyanate compound, and more preferably contains at least one selected from pentamethylene diisocyanate, hexamethylene diisocyanate, xylylene diisocyanate, isophorone diisocyanate, bis(isocyanatomethyl)cyclohexane, bis(isocyanatocyclohexyl)methane, 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, tolylene diisocyanate, 4,4'-diphenylmethane diisocyanate, and phenylene diisocyanate.

[0018] When the polyiso(thio)cyanate compound (A) contains xylylene diisocyanate, the polyiso(thio)cyanate compound (A) may further contain at least one selected from the group consisting of the following compound (N1), the following compound (N2), and the following compound (N3):

[0019]

[0020] When the polyiso(thio)cyanate compound (A) contains xylylene diisocyanate and compound (N1), it is preferable that the peak area of ​​compound (N1) measured by gas chromatography under the following GC condition 1 is 0.20 ppm or more relative to the peak area 1 of xylylene diisocyanate. -GC condition 1- Packing: DB-1 (film thickness) 1.5 μm Column: inner diameter 0.53 mm × length 60 m (manufactured by Agilent) Oven temperature: heating from 130°C to 220°C at 3°C / min, and after reaching 220°C, heating to 300°C at 10°C / min Split ratio: pulsed splitless method Injection port temperature: 280°C Detector temperature: 300°C Carrier gas: N ２ 158 kPa, H ２ 55 kPa, Air 45 kPa (constant pressure control) Solvent: Chloroform Sample concentration: 2.0 mass% chloroform solution Injection amount: 2 μL Detection method: FID

[0021] The peak area of ​​the compound (N1) is more preferably 5.0 ppm or more, even more preferably 50 ppm or more, and even more preferably 100 ppm or more, relative to the peak area of ​​xylylene diisocyanate 1. The peak area of ​​the compound (N1) is preferably 4000 ppm or less, more preferably 3000 ppm or less, even more preferably 2000 ppm or less, even more preferably 1500 ppm or less, and even more preferably 1000 ppm or less, relative to the peak area of ​​xylylene diisocyanate 1. The peak area of ​​the compound (N1) can be measured in accordance with the method described in paragraph 0377 of Japanese Patent No. 6373536.

[0022] When the polyiso(thio)cyanate compound (A) contains xylylene diisocyanate and compound (N2), the peak area of ​​compound (N2) in gas chromatography measurement under the following GC condition 2 is preferably 0.05 ppm or more relative to the peak area of ​​xylylene diisocyanate, 1. -GC condition 2- Column: HP-50+, inner diameter 0.25 mm × length 30 m × film thickness 0.25 μm (manufactured by Hewlett-Packard Company) Oven temperature: temperature increased from 50°C to 280°C at a rate of 10°C / min, and held for 6 minutes after reaching 280°C. Split ratio: pulsed splitless method Injection port temperature: 200°C Detector temperature: 280°C Carrier gas: He Carrier gas flow rate: 1.0 ml / min (constant flow rate control) Sample concentration: 1.0 mass% dichloromethane solution Injection amount: 1.0 μL Detection method: SIM (monitoring ions: m / z 180, 215) (content ratio of xylylene diisocyanate)

[0023] The peak area of ​​the compound (N2) is more preferably 0.1 ppm or more, even more preferably 0.3 ppm or more, and even more preferably 0.6 ppm or more, relative to the peak area of ​​xylylene diisocyanate 1. The peak area of ​​the compound (N2) is preferably 200 ppm or less, more preferably 150 ppm or less, even more preferably 100 ppm or less, even more preferably 80 ppm or less, even more preferably 70 ppm or less, and even more preferably 60 ppm or less, relative to the peak area of ​​xylylene diisocyanate 1. The peak area of ​​the compound (N2) can be measured in accordance with the method described in paragraphs 0375 and 0376 of Japanese Patent No. 6,373,536.

[0024] When the polyiso(thio)cyanate compound (A) contains xylylene diisocyanate and compound (N3), the peak area of ​​compound (N3) measured by gas chromatography under the above-mentioned GC condition 1 is preferably 0.10 ppm or more relative to the peak area of ​​xylylene diisocyanate. The peak area of ​​compound (N3) is more preferably 0.1 ppm or more, even more preferably 3.0 ppm or more, and even more preferably 5.0 ppm or more relative to the peak area of ​​xylylene diisocyanate. The peak area of ​​compound (N3) is preferably 1000 ppm or less, more preferably 500 ppm or less, even more preferably 300 ppm or less, even more preferably 100 ppm or less, and even more preferably 75 ppm or less relative to the peak area of ​​xylylene diisocyanate. The peak area of ​​compound (N3) can be measured in accordance with the method described in paragraph 0377 of Japanese Patent No. 6373536.

[0025] The acid content of the polyiso(thio)cyanate compound (A) is preferably 3000 ppm or less, more preferably 2000 ppm or less, even more preferably 1000 ppm or less, even more preferably 100 ppm or less, even more preferably 50 ppm or less, even more preferably 30 ppm or less, and even more preferably less than 15 ppm. The lower limit of the acid content of the polyiso(thio)cyanate compound (A) is not particularly limited, but the lower limit is, for example, 1 ppm. The acid content of the polyiso(thio)cyanate compound (A) can be measured in accordance with the method described in paragraph 0091 of WO 2021 / 256417. The polyiso(thio)cyanate compound (A) may contain a stabilizer.

[0026] When the polymerizable composition of the present disclosure contains a polythiol compound (B1) as the active hydrogen compound (B) described later, the mixing ratio of the polythiol compound (B1) to the polyiso(thio)cyanate compound (A) is such that the molar ratio of mercapto groups contained in the polythiol compound (B1) to the iso(thio)cyanate groups of the polyiso(thio)cyanate compound (A) (mercapto groups / iso(thio)cyanate groups) is preferably 0.5 to 3.0, more preferably 0.6 to 2.0, and even more preferably 0.8 to 1.3.

[0027] <Active Hydrogen Compound (B)> The polymerizable composition of the present disclosure contains at least one active hydrogen compound (B).

[0028] In the present disclosure, an active hydrogen compound refers to a compound containing an active hydrogen group, such as a hydroxyl group, a mercapto group (i.e., a thiol group), a primary amino group, or a secondary amino group.

[0029] Examples of the active hydrogen compound (B) include polythiol compounds (B1) (i.e., compounds containing two or more mercapto groups (i.e., thiol groups)), polyol compounds (B2) (i.e., compounds containing two or more hydroxyl groups), hydroxythiol compounds (B3) (i.e., compounds containing one or more hydroxyl groups and one or more mercapto groups), polyamine compounds (B4) (i.e., compounds containing two or more amino groups), and the like. For these compounds, the descriptions in WO 2021 / 153631 and WO 2021 / 153632 can be appropriately referenced.

[0030] (Polythiol Compound (B1)) As the active hydrogen compound (B), a polythiol compound (B1) is preferred. The polythiol compound (B1) is not particularly limited as long as it is a compound containing two or more mercapto groups. The polythiol compound (B1) that can be contained in the polymerizable composition of the present disclosure may be one type of compound or two or more types of compounds.

[0031] Examples of the polythiol compound (B1) include 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, 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, pentaerythritol tetrakis(2-mercaptoacetate), pentaerythritol tetrakis(3-mercaptopropionate), 2,5-bis(mercaptomethyl)-1,4-dithiane, bis(mercaptoethyl)sulfide, 1,1,3,3-tetrakis(mercaptomethylthio)propane, The polythiol compound (B1) preferably contains at least one selected from the group consisting of 4,6-bis(mercaptomethylthio)-1,3-dithiane, 2-(2,2-bis(mercaptomethylthio)ethyl)-1,3-dithietane, 1,1,2,2-tetrakis(mercaptomethylthio)ethane, 3-mercaptomethyl-1,5-dimercapto-2,4-dithiapentane, tris(mercaptomethylthio)methane, and ethylene glycol bis(3-mercaptopropionate) (hereinafter also referred to as "polythiol T"). It is more preferable that the polythiol compound (B1) contains polythiol T as a main component.

[0032] Here, "the polythiol compound (B1) contains polythiol T as a main component" means that the total content of polythiol T relative to the total amount of polythiol compound (B1) is 50% or more. The total content of polythiol T relative to the total amount of polythiol compound (B1) is preferably 60% or more, more preferably 70% or more, and even more preferably 80% or more. Here, "%" means the ratio (area %) of the total area of ​​all peaks of polythiol T relative to the total area of ​​all peaks of polythiol compound (B1) determined by high performance liquid chromatography.

[0033] More specific embodiments of the polythiol compound (B1) include: an embodiment containing 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane (hereinafter also referred to as "polythiol T1") as a main component; an embodiment containing at least one selected from the group consisting of 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, and 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane (hereinafter also referred to as "polythiol T2") as a main component; an embodiment containing pentaerythritol tetrakis(3-mercaptopropionate) (hereinafter also referred to as "polythiol T3") as a main component; an embodiment containing polythiol T1 and polythiol T3 as main components; The term "contains as a main component" as used herein is the same as the term "contains as a main component" in the description of "Polythiol T" above.

[0034] When the polythiol compound (B1) contains a compound containing three or more mercapto groups (for example, at least one of the polythiols T1 to T3 described above), the polythiol compound (B1) may contain a compound in which at least one of the three or more mercapto groups contained in the compound containing three or more mercapto groups is substituted with a group represented by the following formula (S1) (hereinafter also referred to as compound (S1)). This can further promote the polymerization reaction.

[0035]

[0036] In formula (S1), * represents a bonding position.

[0037] In the polythiol compound (B1) of an embodiment comprising a compound containing three or more mercapto groups (for example, at least one of the polythiols T1 to T3 described above) and the compound (S1), when the peak area is measured by high performance liquid chromatography, the peak area of ​​the compound (S1) is preferably 0.01 to 3.0, more preferably 0.01 to 1.5, relative to 100 of the peak area of ​​the compound containing three or more mercapto groups. When the peak area of ​​the compound (S1) is 0.01 or more relative to 100 of the peak area of ​​the compound containing three or more mercapto groups, the polymerization reaction is further promoted. When the peak area of ​​the compound (S1) is 3.0 or less relative to 100 of the peak area of ​​the compound containing three or more mercapto groups, the controllability of the polymerization reaction is excellent.

[0038] In the polymerizable composition of the present disclosure, the total content of the polyiso(thio)cyanate compound (A) and the active hydrogen compound (B) is preferably 70% by mass or more, more preferably 80% by mass or more, and even more preferably 90% by mass or more, based on the total amount of the polymerizable composition. The upper limit of the total content of the polyiso(thio)cyanate compound (A) and the active hydrogen compound (B) is, for example, 98% by mass or less, based on the total amount of the polymerizable composition.

[0039] <Nitrogen-Containing Compound (C)> The polymerizable composition of the present disclosure contains at least one nitrogen-containing compound (C), which is at least one of a nitrogen-containing aromatic heterocyclic compound and a tertiary amine compound. The nitrogen-containing compound (C) can function as a curing catalyst. The nitrogen-containing compound (C) contributes to suppressing opacity and striae in a resin obtained by curing the polymerizable composition.

[0040] The nitrogen-containing aromatic heterocyclic compound as the nitrogen-containing compound (C) is not particularly limited, but is preferably a compound represented by the following formula (1): The tertiary amine compound as the nitrogen-containing compound (C) is not particularly limited, but is preferably a compound represented by the following formula (2):

[0041] The nitrogen-containing compound (C) preferably contains at least one of a compound represented by the following formula (1) and a compound represented by the following formula (2).

[0042] (Compound Represented by Formula (1)) The compound represented by formula (1) is as follows: The compound represented by formula (1) is included in the concept of a nitrogen-containing aromatic heterocyclic compound.

[0043]

[0044] In formula (1), m R １ each independently 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; Q represents a carbon atom or a nitrogen atom; and m represents an integer of 0 to 5.

[0045] In formula (1), m R １ each independently 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; Q represents a carbon atom, a nitrogen atom, or an oxygen atom; and m represents an integer of 0 to 5.

[0046] In formula (1), m is preferably an integer of 0 to 3, and more preferably an integer of 1 to 3.

[0047] In formula (1), R １ Examples of the linear alkyl group having 1 to 20 carbon atoms represented by the formula (1) include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, a pentyl group, a hexyl group, a heptyl group, an n-octyl group, a nonyl group, a decyl group, and a dodecyl group. １ Examples of the branched alkyl group having 3 to 20 carbon atoms represented by the formula (1) include an isopropyl group, an isobutyl group, a t-butyl group, an isopentyl group, an isooctyl group, a 2-ethylhexyl group, a 2-propylpentyl group, and an isodecyl group. １ Examples of the cycloalkyl group having 3 to 20 carbon atoms represented by the formula (I) include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group.

[0048] In formula (1), R １ is preferably a linear alkyl group having 1 to 20 carbon atoms or a halogen atom, and more preferably a linear alkyl group having 1 to 3 carbon atoms or a chlorine atom.

[0049] The compound represented by formula (1) is preferably at least one selected from the group consisting of 2-methylpyrazine, pyridine, α-picoline, β-picoline, γ-picoline, 2,6-lutidine, 3,5-lutidine, 2,4,6-trimethylpyridine, 3-chloropyridine, 2-ethylpyridine, and 3-ethylpyridine.

[0050] (Compound Represented by Formula (2)) The compound represented by formula (2) is as follows: The compound represented by formula (2) is included in the concept of a tertiary amine compound.

[0051]

[0052] In formula (2), R ２ , R ３ , and R ４ R each independently represents a linear alkyl group having 3 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. ２ and R ３ may be bonded to each other to form a ring.

[0053] In formula (2), R ２ , R ３ , and R ４ are each independently preferably a linear alkyl group having 3 to 20 carbon atoms, more preferably a linear alkyl group having 3 to 10 carbon atoms, and particularly preferably a linear alkyl group having 5 to 10 carbon atoms.

[0054] R ２ , R ３ , or R ４ Examples of the linear alkyl group having 3 to 20 carbon atoms represented by the formula (I) include an n-propyl group, an n-butyl group, a pentyl group, a hexyl group, a heptyl group, an n-octyl group, a nonyl group, a decyl group, and a dodecyl group.

[0055] R ２ and R ３ may be bonded to each other to form a ring. That is, the compound represented by formula (2) ２ and R ３may be a cyclic amine compound having a structure in which the groups bond to each other to form a ring. Examples of the cyclic amine compound include 1-propylpiperidine, 1-butylpiperidine, 1-cyclohexylpiperidine, 1-butylpyrrolidine, and 1-cyclohexylpyrrolidine.

[0056] The compound represented by formula (2) is preferably at least one selected from the group consisting of triallylamine and trioctylamine.

[0057] The content of the nitrogen-containing compound (C) in the polymerizable composition (i.e., the total content of the nitrogen-containing aromatic heterocyclic compound and the tertiary amine compound; for example, the total content of the compound represented by Formula (1) and the compound represented by Formula (2)) is preferably 0.01% by mass to 1% by mass, and more preferably 0.01% by mass to 0.5% by mass, based on the total content of the polyiso(thio)cyanate compound (A) and the active hydrogen compound (B).

[0058] The content of the nitrogen-containing compound (C) in the polymerizable composition (i.e., the total content of the nitrogen-containing aromatic heterocyclic compound and the tertiary amine compound; for example, the total content of the compound represented by Formula (1) and the compound represented by Formula (2)) is preferably 0.01% by mass to 1% by mass, and more preferably 0.01% by mass to 0.5% by mass, relative to the total amount of the polymerizable composition.

[0059] For the content of the nitrogen-containing compound (C) in the polymerizable composition, reference may be made to WO 2021 / 153631 and WO 2021 / 153632.

[0060] The polymerizable composition of the present disclosure may contain a compound other than the nitrogen-containing compound (C) as a curing catalyst, provided that the proportion of the nitrogen-containing compound (C) in the curing catalyst is preferably 50% by mass to 100% by mass, more preferably 60% by mass to 100% by mass, even more preferably 80% by mass to 100% by mass, and still more preferably 90% by mass to 100% by mass.

[0061] <Water> The polymerizable composition of the present disclosure contains water. The water content is 1,900 ppm by mass or less based on the total amount of the polymerizable composition.

[0062] As described above, in general, when a nitrogen-containing compound (C) is added as a curing catalyst to a polymerizable composition containing a polyiso(thio)cyanate compound (A) and an active hydrogen compound (B), devitrification of the resulting resin may not be suppressed. In contrast, in the polymerizable composition of the present disclosure, the water content is 1900 ppm by mass or less relative to the total amount of the polymerizable composition, thereby suppressing devitrification of the resulting resin.

[0063] From the viewpoint of more effectively suppressing devitrification, the water content is preferably 1500 ppm by mass or less, and more preferably 1100 ppm by mass or less, based on the total amount of the polymerizable composition.

[0064] From the viewpoint of further improving the production suitability of the polythiol composition and / or the polymerizability of the monomer, the water content is preferably 10 ppm by mass or more, more preferably 100 ppm by mass or more, and even more preferably 200 ppm by mass or more, relative to the total amount of the polymerizable composition.

[0065] <Other Components> The polymerizable composition of the present disclosure may contain components other than the above-described components. Examples of other components include an internal mold release agent, a resin modifier, a chain extender, a crosslinking agent, a radical scavenger, a light stabilizer, an ultraviolet absorber, an antioxidant, an oil-soluble dye, a filler, an adhesion improver, an antibacterial agent, an antistatic agent, a dye, a blue ink agent such as a fluorescent whitening agent, a fluorescent pigment, or an inorganic pigment.

[0066] The internal mold release agent may be an acidic phosphate ester. Examples of the acidic phosphate ester include a phosphate monoester and a phosphate diester, and these may be used alone or in combination of two or more.

[0067] The polymerizable composition of the present disclosure may further contain a prepolymer which is a polymer (i.e., a reaction product) of a polyiso(thio)cyanate compound (A) and an active hydrogen compound (B) and has a polymerizable functional group. Examples of the polymerizable functional group include an iso(thio)cyanato group, which is a polymerizable functional group contained in the polyiso(thio)cyanate compound (A), and an active hydrogen group (e.g., a mercapto group) contained in the active hydrogen compound (B). For details of the prepolymer, see, for example, International Publication Nos. 2021 / 153631 and 2021 / 153632.

[0068] The method for producing the polymerizable composition of the present disclosure is not particularly limited, and any known method for mixing the above-mentioned components can be appropriately applied. An example of the method for producing the polymerizable composition of the present disclosure (hereinafter also referred to as Production Method A) is as follows, but the method for producing the polymerizable composition of the present disclosure is not limited to Production Method A.

[0069] [Example of a method for producing a polymerizable composition (Production method A)] Production method A includes a step of mixing (hereinafter also referred to as a mixing step) a raw material composition (BX) containing an active hydrogen compound (B) and water, wherein the water content is 3800 mass ppm or less based on the total amount of the raw material composition (BX), a polyiso(thio)cyanate compound (A), and a nitrogen-containing compound (C). In the mixing step, in addition to the components described above, components other than the components described above may be mixed. Production method A may include other steps other than the mixing step.

[0070] In the mixing step of Production Method A, raw material composition (BX) is used. Raw material composition (BX) contains an active hydrogen compound (B) and water, and has a water content of 3800 ppm by mass or less, based on the total amount of raw material composition (BX). The water content in raw material composition (BX) is preferably 2200 ppm by mass or less, more preferably 1000 ppm by mass or less. The water content in raw material composition (BX) is preferably 10 ppm by mass or more, more preferably 100 ppm by mass or more, even more preferably 200 ppm by mass or more, even more preferably 300 ppm by mass or more, and even more preferably 400 ppm by mass or more.

[0071] In Production Method A, the order in which the raw materials (i.e., raw material composition (BX), polyiso(thio)cyanate compound (A), and nitrogen-containing compound (C)) are mixed (i.e., the order in which they are charged into a container used for mixing) is not particularly limited. For example, the polymerizable composition may be obtained by charging all of the raw materials into a container at once and mixing them, or by adding the raw materials little by little to the container and mixing them. Alternatively, the polymerizable composition may be obtained by first charging a portion of the total amount of the raw materials into a container to form a prepolymer having a polymerizable functional group as a polymer of the polyiso(thio)cyanate compound (A) and the active hydrogen compound (B), and then adding the rest of the raw materials to obtain a polymerizable composition containing the polyiso(thio)cyanate compound (A), the active hydrogen compound (B), the nitrogen-containing compound (C), the prepolymer having a polymerizable functional group, and water.

[0072] [Resin, Molded Article] The resin of the present disclosure is a cured product of the polymerizable composition of the present disclosure. The molded article of the present disclosure contains the resin of the present disclosure.

[0073] That is, the resin of the present disclosure can be produced by curing the above-described polymerizable composition of the present disclosure, specifically by polymerizing and curing the monomers in the polymerizable composition of the present disclosure.

[0074] Examples of methods for polymerizing the monomers in the polymerizable composition of the present disclosure include cast polymerization, which can produce a molded article of the present disclosure containing the resin of the present disclosure (i.e., a cured product of the polymerizable composition of the present disclosure).

[0075] In cast polymerization, first, a polymerizable composition according to one example of the present disclosure is injected between a pair of molds held together by a gasket, tape, or the like. At this time, degassing, filtration, or the like may be performed as necessary. Next, the monomer in the composition injected between the molds is polymerized to harden the composition between the molds and obtain a cured product. The cured product is then removed from the molds to obtain a cured product. Polymerization of the monomer may be performed by heating the polymerizable composition according to the present disclosure. This heating can be performed, for example, using a heating device equipped with a mechanism for heating an object to be heated in an oven, water, or the like.

[0076] The polymerization conditions (e.g., polymerization temperature, polymerization time, etc.) for polymerizing the monomers in the polymerizable composition of the present disclosure are appropriately set in consideration of the composition, the type and amount of monomers used in the composition, the type and amount of polymerization catalyst used in the composition, the shape of the mold, etc. Examples of the polymerization temperature include −50° C. to 150° C., 10° C. to 150° C., etc. Examples of the polymerization time include 1 hour to 200 hours, 1 hour to 80 hours, etc.

[0077] The resin or resin-containing molded article of the present disclosure may be obtained by subjecting the monomer to polymerization followed by treatment such as annealing, etc. Annealing temperatures include 50°C to 150°C, 90°C to 140°C, and 100°C to 130°C.

[0078] [Optical Material] The optical material of the present disclosure includes the resin of the present disclosure described above. The optical material of the present disclosure can be produced, for example, by the above-mentioned cast polymerization.

[0079] The optical material of the present disclosure may be made of the resin of the present disclosure, or may contain the resin of the present disclosure and other elements, such as other members and a coating layer provided on the resin of the present disclosure.

[0080] Optical materials of the present disclosure include lenses (e.g., eyeglass lenses, camera lenses, polarized lenses, etc.), light-emitting diodes (LEDs), and the like.

[0081] [Lens] The lens of the present disclosure is an example of the optical material of the present disclosure, and contains the resin of the present disclosure described above. The lens of the present disclosure can be manufactured, for example, by the cast polymerization described above.

[0082] The lens of the present disclosure may be made of the resin of the present disclosure, or may include the resin of the present disclosure and other elements, such as other members and a coating layer provided on the resin of the present disclosure.

[0083] Lenses according to the present disclosure include eyeglass lenses, camera lenses, polarized lenses, etc. Hereinafter, eyeglass lenses will be described as an example of lenses according to the present disclosure. The eyeglass lenses contain the resin according to the present disclosure molded into a desired lens shape. The eyeglass lenses preferably further contain a coating layer provided on one or both sides of the resin.

[0084] Specific examples of the coating layer include a primer layer, a hard coat layer, an antireflection layer, an antifogging coat layer, an antifouling layer, and a water-repellent layer. Each of these coating layers can be used alone, or multiple coating layers can be used in combination. When coating layers are applied to both sides of the cured product, the same coating layer or different coating layers can be applied to each side.

[0085] The components of the coating layer can be appropriately selected depending on the purpose, and examples of the components of the coating layer include resins (e.g., urethane resins, epoxy resins, polyester resins, melamine resins, polyvinyl acetal resins, etc.), infrared absorbers, light stabilizers, antioxidants, photochromic compounds, dyes, pigments, and antistatic agents.

[0086] For details about eyeglass lenses and coating layers, reference can be made to the descriptions in publicly known documents such as JP 2002-194083 A and WO 2017 / 047745 A, as appropriate.

[0087] Examples of the present disclosure will be shown below, but the present disclosure is not limited to the following examples. Unless otherwise specified, "parts" and "%" are based on mass.

[0088] Examples 1 to 3, and Comparative Examples 1 and 2: <Production of Polythiol Compound (B1-1)> A polythiol compound (B1-1) containing polythiol T1 as a main component was produced. Here, polythiol compound (B1-1) is an example of an active hydrogen compound (B). Details are provided below. A reactor was charged with 124.6 parts by mass of 2-mercaptoethanol and 18.3 parts by mass of degassed water. 101.5 parts by mass of a 32% by mass aqueous sodium hydroxide solution was added dropwise over 40 minutes at 12°C to 35°C, followed by 73.6 parts by mass of epichlorohydrin at 29°C to 36°C over 4.5 hours, followed by stirring for 40 minutes. As a result, 1,3-bis(2-hydroxyethylthio)-2-propanol was produced in the reactor. This production was confirmed by NMR data. Next, 331.5 parts by mass of 35.5% by mass hydrochloric acid was charged into the reactor, followed by 183.8 parts by mass of 99.90% by mass thiourea, and then the mixture was stirred at 110°C reflux for 3 hours to carry out a thiuronium chloride reaction. Next, the liquid in the reactor was cooled to 45°C, and then 320.5 parts by mass of toluene was added thereto. The resulting liquid was cooled to 31°C, and then 243.1 parts by mass of 25% by mass aqueous ammonia solution was added thereto at 31°C to 41°C over 44 minutes, followed by stirring at 54°C to 62°C for 3 hours to carry out a hydrolysis reaction. As a result, a toluene solution of polythiol compound (B1-1) composed mainly of polythiol T1 (i.e., 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane) was obtained. This toluene solution was acid washed with 162.8 parts by mass of 35.5% by mass hydrochloric acid at 35°C to 43°C for 1 hour. The toluene solution after the acid washing was washed twice with 174.1 parts by mass of degassed water at 35°C to 45°C for 30 minutes. The toluene solution after the second washing with degassed water was washed with 162.1 parts by mass of 0.1% by mass ammonia water for 30 minutes. The toluene solution after the ammonia water washing was washed twice with 174.2 parts by mass of degassed water at 35°C to 45°C for 30 minutes.Next, toluene and trace amounts of water were removed from this under heating and reduced pressure, followed by treatment with silica gel column chromatography and subsequent filtration under reduced pressure through a 1.2 μm PTFE-type membrane filter to obtain a polythiol compound (B1-1) (205.0 parts by mass) containing polythiol T1 as a main component.

[0089] <Preparation of Raw Material Composition (BX)> The polythiol compound (B1-1) obtained as described above was mixed with water to obtain raw material composition (BX). The mixing ratio of polythiol compound (B1-1) to water was adjusted so that the water content (mass%) relative to the total amount of raw material composition (BX) would be the value shown in Table 1. Here, the water content relative to the total amount of raw material composition (BX) was measured using a Karl Fischer moisture meter (MKC-710, manufactured by Kyoto Electronics Manufacturing Co., Ltd.).

[0090] <Preparation of Polymerizable Composition> m-xylylene diisocyanate (hereinafter also referred to as "NCO1") (52 parts by mass) as the polyiso(thio)cyanate compound (A) and VIOSORB583 (manufactured by Kyodo Pharmaceutical Co., Ltd.) (1.0 part by mass) as an ultraviolet absorber were mixed, and then 3,5-lutidine (0.03 parts by mass) as the nitrogen-containing compound (C), and JP-506H (manufactured by Johoku Chemical Industry Co., Ltd.; acidic phosphate ester) (0.075 parts by mass) as an internal mold release agent were mixed therewith at 20°C to prepare a mixed liquid, and the resulting mixed liquid was degassed at 600 Pa for 1 hour. Next, raw material composition (BX) that had been degassed in advance at 600 Pa for 1 hour was added to the resulting mixture in an amount that would amount to 47% by mass with respect to the entire composition, and the mixture was mixed at 20°C to obtain a polymerizable composition.

[0091] The water content (ppm by mass) relative to the total amount of the resulting polymerizable composition was measured using a Karl Fischer moisture meter (MKC-710, manufactured by Kyoto Electronics Manufacturing Co., Ltd.), and the values ​​shown in Table 1 were obtained.

[0092] <Production of Resin Molded Article> Next, the polymerizable composition was degassed at 600 Pa for 10 minutes. The degassed polymerizable composition was filtered through a 1 μm Teflon (registered trademark) filter, and the filtrate was poured between a pair of glass molds secured with tape. The pair of glass molds were then placed in an oven, and the temperature inside the oven was set to 30°C. Next, the temperature inside the oven was raised from 30°C to 70°C over 1.5 hours, then from 70°C to 120°C over 0.5 hours, then maintained at 120°C for 1 hour, and then lowered from 120°C to 70°C over 1 hour. Through the above process, the monomers in the polymerizable composition (i.e., NCO1 and polythiol compound (B1-1)) were polymerized, and a molded article containing the resin (i.e., a cured product of the polymerizable composition) was formed between the pair of glass molds. The oven was then cooled, and the pair of glass molds were removed from the oven. The resin-containing molded body (hereinafter referred to as the resin molded body) was then removed from the pair of glass molds. The obtained resin molded body was annealed at 120°C for 1 hour to obtain a circular, flat lens having a thickness of 9.0 mm and a diameter of 75 mm.

[0093] <Measurement and Evaluation of Lens> The circular flat lens (i.e., the resin molded article after annealing) was subjected to the following evaluation. The results are shown in Table 1. In Table 1, "B1-1" means polythiol compound (B1-1).

[0094] (Air Bubbles) The lenses were visually observed and evaluated for air bubbles in the lenses according to the following evaluation criteria: In the following evaluation criteria, rank A indicates that the generation of air bubbles is most suppressed.

[0095] -Evaluation criteria for air bubbles- A. No air bubbles were found throughout the entire lens. B. Air bubbles were found in some parts of the lens. C. Air bubbles were found throughout the entire lens.

[0096] (Striae) The lenses were visually observed and evaluated for striae in the lenses according to the following evaluation criteria: In the following evaluation criteria, rank A indicates that the occurrence of striae is most suppressed.

[0097] --Evaluation criteria for striae-- A. No striae were found over the entire lens. B. Striae were found in part of the lens. C. Striae were found over the entire lens.

[0098] (Devitrification) Light from a light source (Luminar Ace LA-150A manufactured by Hayashi Repic Co., Ltd.) was transmitted through the lens in a dark place. An image of the light transmitted through the lens was captured into an image processing device (manufactured by Ube Information Systems Co., Ltd.), and the captured image was subjected to shading processing. The degree of shading of the processed image was quantified for each pixel, and the average value of the numerical values ​​of the degree of shading for each pixel was obtained to determine the degree of devitrification of the lens. Based on the obtained degree of devitrification, the devitrification of the lens was evaluated according to the following evaluation criteria. In the evaluation criteria below, the rank A is the rank in which devitrification of the lens is most suppressed.

[0099] - Evaluation criteria for devitrification - A: The devitrification degree was less than 35. B: The devitrification degree was 35 or more and less than 50. C: The devitrification degree was 50 or more.

[0100] Example 4, Comparative Examples 3 and 4 <Production of Polythiol Compound (B1-1)> Polythiol compound (B1-1) was produced in the same manner as in Example 1.

[0101] <Production of Polythiol Compound (B1-2)> A polythiol compound (B1-2) containing polythiol T3 (i.e., pentaerythritol tetrakis(3-mercaptopropionate)) as a main component was produced. Here, polythiol compound (B1-2) is an example of the active hydrogen compound (B). Details are provided below. 136.9 parts by mass of pentaerythritol with a purity of 99.5%, 406.3 parts by mass of 3-mercaptopropionic acid, 3.8 parts by mass of p-toluenesulfonic acid monohydrate, and 185.2 parts by mass of toluene were added to a four-necked reaction flask equipped with a stirrer, a Dean-Stark apparatus, a nitrogen gas purge tube, and a thermometer to obtain a mixture. Here, the molar ratio of 3-mercaptopropionic acid to pentaerythritol was 3.80. The temperature of the mixture was then increased using an oil bath. 120 minutes after the start of the temperature increase, reflux began when the internal temperature reached 97°C (oil bath temperature: 113°C). After the start of reflux, the reaction was carried out for 7 hours (internal temperature: 97-121°C). During the reaction, water by-produced under reflux was continuously removed from the system. The amount of water removed from the system was 93.2% of the theoretically produced water. The reaction solution after the reaction was cooled, and then washed with a base and then with water. After the water washing, toluene and trace amounts of water were removed from the reaction solution under heating and reduced pressure. The remaining reaction solution was filtered through a PTFE-type membrane filter to obtain 462.3 parts by mass of a polythiol compound (B1-2) containing polythiol T3 as a main component.

[0102] <Preparation of Raw Material Composition (BX)> The polythiol compound (B1-1), polythiol compound (B1-2), and water obtained as described above were mixed to obtain raw material composition (BX). The mixing ratio of polythiol compound (B1-1), polythiol compound (B1-2), and water was adjusted so that the mass ratio [polythiol compound (B1-1):polythiol compound (B1-2)] was 1:1, and the water content (mass%) relative to the total amount of raw material composition (BX) was the value shown in Table 1. Here, the water content relative to the total amount of raw material composition (BX) was measured using a Karl Fischer moisture meter (MKC-710, manufactured by Kyoto Electronics Manufacturing Co., Ltd.).

[0103] <Preparation of Polymerizable Composition> A mixture of 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane and 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane (hereinafter also referred to as "NCO2") (50.6 parts by mass) as the polyiso(thio)cyanate compound (A) and an ultraviolet absorber VIOSORB583 (manufactured by Kyodo Pharmaceutical Co., Ltd.) (1.0 part by mass) were mixed, and then 3,5-lutidine (0.20 parts by mass) as the nitrogen-containing compound (C), and JP-506H (manufactured by Johoku Chemical Industry Co., Ltd.; acidic phosphate ester) (0.10 parts by mass) as an internal mold release agent were mixed therewith at 20°C to prepare a mixed liquid, and the resulting mixed liquid was degassed at 600 Pa for 1 hour. Next, raw material composition (BX) that had been degassed in advance at 600 Pa for 1 hour was added thereto in an amount that would give 49 mass % based on the total mass of the resulting composition, and the mixture was mixed at 20°C to obtain a polymerizable composition.

[0104] The water content (ppm by mass) relative to the total amount of the resulting polymerizable composition was measured using a Karl Fischer moisture meter (MKC-710, manufactured by Kyoto Electronics Manufacturing Co., Ltd.), and the values ​​shown in Table 1 were obtained.

[0105] <Production of Resin Molded Article> Using the above polymerizable composition, a resin molded article was obtained in the same manner as in the production of the resin molded article in Example 1. The obtained resin molded article was annealed at 120°C for 1 hour to obtain a circular flat lens having a thickness of 9.0 mm and a diameter of 75 mm.

[0106] <Measurement and Evaluation of Lens> The circular flat lens (i.e., the annealed resin molded product) was subjected to the same evaluations as in Example 1. The results are shown in Table 1. In Table 1, "B1-1" means polythiol compound (B1-1), and "B1-2" means polythiol compound (B1-2).

[0107]

[0108] As shown in Table 1, in Examples 1 to 3, which used polymerizable compositions containing a polyiso(thio)cyanate compound (A), an active hydrogen compound (B), a nitrogen-containing compound (C), and water, where the water content was 1900 ppm by mass or less based on the total amount of the polymerizable composition, bubbles, striae, and devitrification were suppressed in the resulting lens (i.e., resin molded product). In contrast to Examples 1 to 3, in Comparative Example 1, which used a polymerizable composition containing a polyiso(thio)cyanate compound (A), an active hydrogen compound (B), a nitrogen-containing compound (C), and water, where the water content was more than 1900 ppm by mass based on the total amount of the polymerizable composition, bubbles and striae were suppressed in the resulting lens (i.e., resin molded product), but devitrification could not be suppressed.

[0109] The disclosure of Japanese Patent Application No. 2023-122891, filed on July 27, 2023, is incorporated herein by reference in its entirety. All documents, patent applications, and technical standards described herein are incorporated herein by reference to the same extent as if each individual document, patent application, and technical standard was specifically and individually indicated to be incorporated by reference.

Claims

1. A polymerizable composition comprising: a polyiso(thio)cyanate compound (A); an active hydrogen compound (B); a nitrogen-containing compound (C) which is at least one of a nitrogen-containing aromatic heterocyclic compound and a tertiary amine compound; and water, wherein the water content is 1,900 ppm by mass or less based on the total amount of the polymerizable composition.

2. The polymerizable composition according to claim 1, wherein the nitrogen-containing compound (C) comprises at least one of a compound represented by the following formula (1) and a compound represented by the following formula (2): [In formula (1), m R １ each independently 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, Q represents a carbon atom or a nitrogen atom, and m represents an integer of 0 to 5. ２ , R ３ , and R ４ R each independently represents a linear alkyl group having 3 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. ２ and R ３ may be bonded to each other to form a ring.

3. The polymerizable composition according to claim 2, wherein the compound represented by formula (1) is at least one selected from the group consisting of 2-methylpyrazine, pyridine, α-picoline, β-picoline, γ-picoline, 2,6-lutidine, 3,5-lutidine, 2,4,6-trimethylpyridine, 3-chloropyridine, 2-ethylpyridine, and 3-ethylpyridine, and the compound represented by formula (2) is at least one selected from the group consisting of triallylamine and trioctylamine.

4. The polymerizable composition according to claim 1, wherein the polyiso(thio)cyanate compound (A) comprises at least one selected from the group consisting of pentamethylene diisocyanate, hexamethylene diisocyanate, xylylene diisocyanate, isophorone diisocyanate, bis(isocyanatomethyl)cyclohexane, bis(isocyanatocyclohexyl)methane, 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, tolylene diisocyanate, 4,4'-diphenylmethane diisocyanate, and phenylene diisocyanate.

5. The polymerizable composition according to claim 1, wherein the active hydrogen compound (B) is a polythiol compound (B1).

6. The polythiol compound (B1) is 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, 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, pentaerythritol tetrakis(3-mercaptopropionate), pentaerythritol tetrakis(2-mercaptoacetate), 2,5-bis(mercapto 6. The polymerizable composition of claim 5, comprising at least one selected from the group consisting of bis(mercaptomethylthio)-1,4-dithiane, bis(2-mercaptoethyl)sulfide, 1,1,3,3-tetrakis(mercaptomethylthio)propane, 4,6-bis(mercaptomethylthio)-1,3-dithiane, 2-(2,2-bis(mercaptomethylthio)ethyl)-1,3-dithietane, 1,1,2,2-tetrakis(mercaptomethylthio)ethane, 3-mercaptomethyl-1,5-dimercapto-2,4-dithiapentane, and tris(mercaptomethylthio)methane.

7. The polymerizable composition according to claim 1, wherein the water content is 100 ppm by mass or more based on the total amount of the polymerizable composition.

8. A method for producing the polymerizable composition according to claim 1, comprising a step of mixing a raw material composition (BX) containing the active hydrogen compound (B) and water, the water content of which is 3,800 ppm by mass or less based on the total amount of the raw material composition (BX), the polyiso(thio)cyanate compound (A), and the nitrogen-containing compound (C).

9. A resin which is a cured product of the polymerizable composition according to any one of claims 1 to 7.

10. A molded article comprising the resin according to claim 9.

11. An optical material comprising the resin according to claim 9.

12. A lens comprising the resin of claim 9.

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