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

Abstract

A polymerizable composition containing a polyiso (thio) cyanate compound (A), an active hydrogen compound (B), a nitrogen-containing compound (C), and water, the nitrogen-containing compound (C) being a nitrogen-containing aromatic heterocyclic compound and / or a tertiary amine compound, and the water content being 1900 ppm by mass or less relative to the total amount of the polymerizable composition.

Description

Technical Field

[0001] This disclosure relates to polymeric compositions and methods of manufacturing thereof, resins, molded articles, optical materials, and lenses. Background Technology

[0002] As a polymerizable composition for manufacturing resin-based optical materials (such as lenses), a polymerizable composition containing an active hydrogen compound (such as a polythiol compound) and a polyisocyanate compound is sometimes used. By polymerizing the monomers (i.e., the active hydrogen compound and the polyisocyanate compound) in this polymerizable composition, an optical material containing resin can be obtained.

[0003] For example, Patent Document 1 discloses a polymerizable composition capable of producing a resin molded article that suppresses turbidity and ripples, comprising: Isocyanate compounds with more than two functionalities; Difunctional or higher active hydrogen compounds (e.g., polythiols); and Non-tin catalysts are composed of compounds with pKa of 1 to 9 having specific chemical structures (e.g., 2-methylpyrazine, β-methylpyridine, γ-methylpyridine, 2,6-dimethylpyridine, 3,5-dimethylpyridine, 3-chloropyridine, triallylamine, and trioctylamine).

[0004] Patent Document 1: International Publication No. 2018-079829 Summary of the Invention

[0005] The problem that the invention aims to solve However, when using the polymerizable composition described in Patent Document 1, which contains the aforementioned specific non-tin catalyst, the resulting resin can suppress turbidity and ripples, but sometimes it cannot suppress devitrification (i.e., devitrification evaluated by devitrification degree).

[0006] One aspect of this disclosure is to provide a polymerizable composition capable of producing a resin that suppresses turbidity, bubbles, and devitrification, a method thereof, and a resin, molded article, and lens that suppress turbidity, bubbles, and devitrification, said polymerizable composition being a composition comprising a polyisocyanate compound (A), an active hydrogen compound (B), a nitrogen-containing compound (C), and water, said nitrogen-containing compound (C) being at least one of a nitrogen-containing aromatic heterocyclic compound and a tertiary amine compound.

[0007] Methods for solving problems The means to solve the above problems include the following methods.

[0008] <1> Polymerizable composition comprising: Polyisocyanate compound (A); Active hydrogen compounds (B); Nitrogen-containing compound (C), wherein the nitrogen-containing compound (C) is at least one of a nitrogen-containing aromatic heterocyclic compound and a tertiary amine compound; and water, The water content is less than 1900 ppm by mass relative to the total amount of the polymeric composition.

[0009] <2> like <1> The polymeric composition wherein the aforementioned nitrogen-containing compound (C) comprises at least one of the compounds represented by formula (1) and the compounds represented by formula (2).

[0010] [Chemical Formula 1] In formula (1), each of the m R1s independently represents a straight-chain alkyl group with 1 to 20 carbon atoms, a branched alkyl group with 3 to 20 carbon atoms, a cycloalkyl group with 3 to 20 carbon atoms, or a halogen atom, Q represents a carbon atom or a nitrogen atom, and m represents an integer from 0 to 5.

[0011] In formula (2), R2, R3 and R4 each independently represent a straight-chain alkyl group with 3 to 20 carbon atoms, a branched alkyl group with 3 to 20 carbon atoms, a cycloalkyl group with 3 to 20 carbon atoms, or an allyl group. R2 and R3 can bond to each other to form a ring.

[0012] <3> like <2> The polymerizable composition wherein the compound represented by the aforementioned formula (1) is at least one selected from the group consisting of 2-methylpyrazine, pyridine, α-methylpyridine, β-methylpyridine, γ-methylpyridine, 2,6-dimethylpyridine, 3,5-dimethylpyridine, 2,4,6-trimethylpyridine, 3-chloropyridine, 2-ethylpyridine, and 3-ethylpyridine. The compound represented by the aforementioned formula (2) is selected from at least one of the groups consisting of triallylamine and trioctylamine.

[0013] <4> like <1> ~ <3> The polymerizable composition according to any one of the above-mentioned polyisocyanate compounds (A) comprises at least one selected from the group consisting of pentamethylene diisocyanate, hexamethylene diisocyanate, phenylene 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, toluene diisocyanate, 4,4'-diphenylmethane diisocyanate, and phenyl diisocyanate.

[0014] <5> like <1> ~ <4> The polymeric composition according to any one of the following methods, wherein the aforementioned active hydrogen compound (B) is a polythiol compound (B1).

[0015] <6> like <5> The polymerizable composition wherein the aforementioned polythiol compound (B1) comprises a subset selected from 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), and pentaerythritol tetrakis (2-mercaptoacetate). At least one of the following groups: 2,5-bis(mercaptomethyl)-1,4-dithiacyclohexane, bis(2-mercaptoethyl) sulfide, 1,1,3,3-tetra(mercaptomethylthio)propane, 4,6-bis(mercaptomethylthio)-1,3-dithiacyclohexane, 2-(2,2-bis(mercaptomethylthio)ethyl)-1,3-dithiacyclobutane, 1,1,2,2-tetra(mercaptomethylthio)ethane, 3-mercaptomethyl-1,5-dimercapto-2,4-dithiapentane, and tri(mercaptomethylthio)methane.

[0016] <7> like <1> ~ <6> The polymeric composition according to any one of the following methods, wherein the water content is 100 ppm by mass or more relative to the total amount of the polymeric composition.

[0017] <8> A method for manufacturing a polymeric composition, which is for manufacturing... <1> ~ <6> The method of any one of the polymeric compositions, The manufacturing method includes a step of mixing a raw material composition (BX), the aforementioned polyisocyanate compound (A), and the aforementioned nitrogen-containing compound (C), wherein the raw material composition (BX) contains the aforementioned active hydrogen compound (B) and water, and the water content is less than 3800 ppm by mass relative to the total amount of the raw material composition (BX).

[0018] <9> Resin, which is <1> ~ <7> The cured product of the polymeric composition described in any one of the above statements.

[0019] <10> Molded body, which includes <9> The aforementioned resin.

[0020] <11> Optical materials, which include <9> The aforementioned resin.

[0021] <12> Lens, which includes <9> The aforementioned resin.

[0022] According to one aspect of this disclosure, a polymerizable composition capable of producing a resin that suppresses turbidity, bubbles, and devitrification, a method for producing the same, and a resin, molded article, and lens that suppress turbidity, bubbles, and devitrification are provided, said polymerizable composition being a composition comprising a polyisocyanate compound (A), an active hydrogen compound (B), a nitrogen-containing compound (C), and water, said nitrogen-containing compound (C) being at least one of a nitrogen-containing aromatic heterocyclic compound and a tertiary amine compound. Detailed Implementation

[0023] In this public document, the range of values ​​indicated by “~” refers to the range of values ​​recorded before and after “~” as the lower and upper limits.

[0024] In this disclosure, the amount of each component in the composition, unless otherwise specified, refers to the total amount of the various substances present in the composition when multiple substances belonging to each component are present in the composition.

[0025] In the numerical ranges described in this disclosure, the upper or lower limit of one numerical range can be replaced with the upper or lower limit of another numerical range described in other stages. Furthermore, the upper or lower limit of a numerical range described in this disclosure can be replaced with the values ​​shown in the embodiments.

[0026] [Polymerizable Composition] The polymeric composition disclosed herein comprises: Polyisocyanate compound (A); Active hydrogen compounds (B); Nitrogen-containing compound (C), wherein the nitrogen-containing compound (C) is at least one of a nitrogen-containing aromatic heterocyclic compound and a tertiary amine compound; and water, The water content is less than 1900 ppm by mass relative to the total amount of the polymeric composition.

[0027] According to the polymerizable composition disclosed herein, it is possible to manufacture a resin that suppresses turbidity, bubbles, and devitrification.

[0028] Here, the effect of suppressing turbidity and bubbles is achieved by using a nitrogen-containing compound (C) as a curing catalyst.

[0029] The effect of suppressing devitrification is achieved by keeping the water content below 1900 ppm by mass relative to the total amount of the polymeric composition.

[0030] In detail, when a nitrogen-containing compound (C) is used as a curing catalyst, although turbidity and ripples can be suppressed, devitrification (i.e., devitrification evaluated by devitrification degree) is sometimes not suppressed.

[0031] In this regard, in the polymeric composition disclosed herein, by making the water content less than 1900 ppm by mass relative to the total amount of the polymeric composition, the effects of suppressing turbidity and ripples can be obtained, and the effect of suppressing devitrification can also be obtained.

[0032] <Polyisocyanate compound (A)> The polymeric compositions disclosed herein contain at least one polyisocyanate compound (A).

[0033] As a polyisocyanate compound (A), there are no particular limitations as long as it is a compound having at least two isocyanate groups in one molecule.

[0034] As a polyisocyanate compound (A), specifically, examples include: Tetramethylene diisocyanate, pentamethylene diisocyanate, hexamethylene diisocyanate, heptamethylene diisocyanate, octamethylene diisocyanate, 2,2,4-trimethylhexamethylene diisocyanate, 2,4,4-trimethylhexamethylene diisocyanate, lysine methyl ester diisocyanate, lysine triisocyanate, phenylene diisocyanate and other aliphatic polyisocyanate compounds; Alicyclic polyisocyanate compounds, including isophorone diisocyanate, bis(isocyanate-methyl)cyclohexane, bis(isocyanate-cyclohexyl)methane, dicyclohexyl dimethylmethane diisocyanate, 2,5-bis(isocyanate-methyl)bicyclo-[2.2.1]-heptane, 2,6-bis(isocyanate-methyl)bicyclo-[2.2.1]-heptane, 3,8-bis(isocyanate-methyl)tricyclodecane, 3,9-bis(isocyanate-methyl)tricyclodecane, 4,8-bis(isocyanate-methyl)tricyclodecane, and 4,9-bis(isocyanate-methyl)tricyclodecane; Aromatic polyisocyanate compounds such as toluene diisocyanate, 4,4'-diphenylmethane diisocyanate, diphenyl sulfide-4,4'-diisocyanate, and phenyl diisocyanate. 2,5-Diisocyanate-thiophene, 2,5-bis(isocyanate-methyl)thiophene, 2,5-diisocyanate-tetrahydrothiophene, 2,5-bis(isocyanate-methyl)tetrahydrothiophene, 3,4-bis(isocyanate-methyl)tetrahydrothiophene, 2,5-diisocyanate-1,4-dithiocyclohexane, 2,5-bis(isocyanate-methyl)-1,4-dithiocyclohexane, 4,5-diisocyanate-1,3-dithiocyclopentane, 4,5-bis(isocyanate-methyl)-1,3-dithiocyclopentane and other heterocyclic polyisocyanate compounds; Aliphatic polyisothiocyanate compounds such as hexamethylene diisothiocyanate, lysine methyl ester diisothiocyanate, lysine triisothiocyanate, and phenylene diisothiocyanate. Isophorone diisothiocyanate, bis(isothiocyanate methyl)cyclohexane, bis(isothiocyanate cyclohexyl)methane, cyclohexane diisothiocyanate, methylcyclohexane diisothiocyanate, 2,5-bis(isothiocyanate methyl)bicyclo-[2.2.1]-heptane, 2,6-bis(isothiocyanate methyl)bicyclo-[2.2.1]-heptane, 3,8-bis(isothiocyanate methyl)tricyclodecane, 3,9-bis(isothiocyanate methyl)tricyclodecane, 4,8-bis(isothiocyanate methyl)tricyclodecane, 4,9-bis(isothiocyanate methyl)tricyclodecane, and other alicyclic polyisothiocyanate compounds; Aromatic polyisothiocyanate compounds such as toluene diisothiocyanate, 4,4'-diphenylmethane diisothiocyanate, and diphenyl sulfide-4,4'-diisothiocyanate. 2,5-Diisothiocyanate-based thiophene, 2,5-bis(isothiocyanate-based methyl)thiophene, 2,5-isothiocyanate-based tetrahydrothiophene, 2,5-bis(isothiocyanate-based methyl)tetrahydrothiophene, 3,4-bis(isothiocyanate-based methyl)tetrahydrothiophene, 2,5-diisothiocyanate-1,4-dithiacyclohexane, 2,5-bis(isothiocyanate-based methyl)-1,4-dithiacyclohexane, 4,5-diisothiocyanate-1,3-dithiacyclopentane, 4,5-bis(isothiocyanate-based methyl)-1,3-dithiacyclopentane, and other sulfur-containing heterocyclic polyisothiocyanate compounds.

[0035] Polyisocyanate compounds may contain at least one selected from among them.

[0036] In addition, as a polyisocyanate compound (A), its halogen-substituted derivatives such as chlorinated derivatives and bromine-substituted derivatives, alkyl-substituted derivatives, alkoxy-substituted derivatives, nitro-substituted derivatives, prepolymer-type modified derivatives with polyols, carbodiimide-modified derivatives, urea-modified derivatives, biuret-modified derivatives, dimerization or trimerization reaction products, etc., can also be used.

[0037] The polyisocyanate compound (A) preferably contains a polyisocyanate compound. Preferably, it comprises at least one selected from pentamethylene diisocyanate, hexamethylene diisocyanate, phenylene 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, toluene diisocyanate, 4,4'-diphenylmethane diisocyanate, and phenyl diisocyanate.

[0038] In the case where the polyisocyanate compound (A) contains phenylene diisocyanate, the polyisocyanate compound (A) may further contain at least one compound selected from the group consisting of compound (N1), compound (N2), and compound (N3).

[0039] [Chemical Formula 2] When the polyisocyanate compound (A) includes phenylene diisocyanate and compound (N1), the peak area of ​​compound (N1) in the gas chromatographic determination under the following GC conditions 1 is preferably 0.20 ppm or more relative to the peak area 1 of phenylene diisocyanate.

[0040] -GC Condition 1- Filler: DB-1 (film thickness) 1.5μm Column: Inner diameter 0.53mm × length 60m (manufactured by Agilent Technologies) Column oven temperature: Increase from 130℃ to 220℃ at 3℃ / min, and after reaching 220℃, increase to 300℃ at 10℃ / min.

[0041] Shunt ratio: Pulse shunt method Inlet temperature: 280℃ Detector temperature: 300℃ Carrier gas: N2 158kPa, H2 55kPa, air 45kPa (constant pressure control) Solvent: Chloroform Sample concentration: 2.0% chloroform solution Injection volume: 2μL Detection method: FID The peak area of ​​the above-mentioned compound (N1) is more preferably 5.0 ppm or more relative to the peak area 1 of phenylene diisocyanate, more preferably 50 ppm or more, and more preferably 100 ppm or more.

[0042] The peak area of ​​the above 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 1 of phenylene diisocyanate.

[0043] The peak area of ​​the above compound (N1) can be determined according to the method described in paragraph 0377 of Japanese Patent No. 6373536.

[0044] When the polyisocyanate compound (A) includes phenylene diisocyanate and compound (N2), the peak area of ​​compound (N2) in the gas chromatographic determination under the following GC conditions 2 is preferably 0.05 ppm or more relative to the peak area 1 of phenylene diisocyanate.

[0045] -GC Condition 2- Column: HP-50+, inner diameter 0.25mm × length 30m × film thickness 0.25μm (manufactured by Hewlett-Packard Company) Column oven temperature: Increase from 50℃ to 280℃ at a rate of 10℃ / min, and hold at 280℃ for 6 minutes.

[0046] Shunt ratio: Pulse shunt method Inlet temperature: 200℃ Detector temperature: 280℃ Carrier gas: He Carrier gas flow rate: 1.0 ml / min (constant flow control) Sample concentration: 1.0% by mass dichloromethane solution Injection volume: 1.0 μL Detection method: SIM (monitoring ions: m / z 180, 215) (content of diphenylene diisocyanate) The peak area of ​​the above compound (N2) is more preferably 0.1 ppm or more, more preferably 0.3 ppm or more, and more preferably 0.6 ppm or more, relative to the peak area 1 of phenylene diisocyanate.

[0047] The peak area of ​​the above 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 1 of phthalic acid diisocyanate.

[0048] The peak area of ​​the above compound (N2) can be determined according to the method described in paragraphs 0375 and 0376 of Japanese Patent No. 6373536.

[0049] When the polyisocyanate compound (A) includes phenylene diisocyanate and compound (N3), the peak area of ​​compound (N3) in the gas chromatographic determination under the aforementioned GC conditions 1 is preferably 0.10 ppm or more relative to the peak area 1 of phenylene diisocyanate.

[0050] The peak area of ​​the above compound (N3) is more preferably 0.1 ppm or more relative to the peak area 1 of phenylene diisocyanate, more preferably 3.0 ppm or more, and more preferably 5.0 ppm or more.

[0051] The peak area of ​​the above 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 1 of phthalic acid diisocyanate.

[0052] The peak area of ​​the above compound (N3) can be determined according to the method described in paragraph 0377 of Japanese Patent No. 6373536.

[0053] The acid content of the polyisocyanate 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.

[0054] There is no particular limit to the lower limit of the acid content of polyisocyanate compound (A), but the lower limit is, for example, 1 ppm.

[0055] The acid content of polyisocyanate compound (A) can be determined according to the method described in paragraph 0091 of International Publication No. 2021 / 256417.

[0056] Polyisocyanate compound (A) may contain a stabilizer.

[0057] When the polymerizable composition of this disclosure contains a polythiol compound (B1) as the active hydrogen compound (B) described later, the molar ratio (thiol group / isocyanate group) of the thiol compound (B1) to the isocyanate group of the polyisocyanate compound (A) is preferably 0.5 to 3.0, more preferably 0.6 to 2.0, and even more preferably 0.8 to 1.3.

[0058] <Active Hydrogen Compounds (B)> The polymeric composition disclosed herein contains at least one active hydrogen compound (B).

[0059] In this publication, the term "active hydrogen compound" refers to a compound containing an active hydrogen group.

[0060] In this publication, the term "active hydrogen group" refers to a hydroxyl group, a mercapto group (i.e., a thiol group), a primary amino group, or a secondary amino group.

[0061] Examples of active hydrogen compounds (B) include: Polythiol compounds (B1) (i.e., compounds containing two or more thiol groups). Polyol compounds (B2) (i.e., compounds containing two or more hydroxyl groups), Hydroxythiols (B3) (i.e., compounds containing one or more hydroxyl groups and one or more thiol groups). Polyamine compounds (B4) (i.e., compounds containing two or more amino groups), etc.

[0062] For information concerning these compounds, reference may be made to International Publication Nos. 2021 / 153631 and 2021 / 153632.

[0063] (Polythiol compound (B1)) As the active hydrogen compound (B), the polythiol compound (B1) is preferred.

[0064] As a polythiol compound (B1), there are no particular restrictions as long as it contains two or more thiol groups.

[0065] The polymeric composition disclosed herein may contain one or more polythiol compounds (B1).

[0066] The polythiol compound (B1) preferably contains selected from 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 tetra(2-mercaptoacetate), Pentaerythritol tetra(3-mercaptopropionate) 2,5-bis(mercaptomethyl)-1,4-dithionecyclohexane, bis(mercaptoethyl) sulfide, 1,1,3,3-Tetra(mercaptomethylthio)propane, 4,6-bis(mercaptomethylthio)-1,3-dithionecyclohexane, 2-(2,2-bis(mercaptomethylthio)ethyl)-1,3-dithionecyclobutane, 1,1,2,2-Tetra(mercaptomethylthio)ethane, 3-Mercaptomethyl-1,5-dimercapto-2,4-dithiapentane, Tris(mercaptomethylthio)methane, and Ethylene glycol bis(3-mercaptopropionate) At least one of the groups (hereinafter also referred to as "polythiol T").

[0067] The polythiol compound (B1) more preferably contains polythiol T as the main component.

[0068] Here, the phrase "polythiol compound (B1) contains polythiol T as the main component" means that the total content of polythiol T is more than 50% relative to the total amount of polythiol compound (B1).

[0069] The total content of polythiols T relative to the total amount of polythiols (B1) is preferably 60% or more, more preferably 70% or more, and even more preferably 80% or more.

[0070] The "%" here refers to 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), as determined by high performance liquid chromatography.

[0071] More specific examples of polythiol compounds (B1) include: The method of containing 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane (hereinafter also referred to as "polythiol T1") as the main component; The method comprising at least one of the following groups selected from 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 the main component; The method of including pentaerythritol tetra(3-mercaptopropionate) (hereinafter also known as "polythiol T3") as the main component; The method includes polythiols T1 and T3 as main components; The method includes polythiols T2 and T3 as main components; etc.

[0072] Here, the meaning of "containing... as a main component" is the same as the meaning of "containing... as a main component" in the aforementioned description of "polythiol T".

[0073] When the polythiol compound (B1) contains a compound having three or more thiol groups (e.g., at least one of the polythiols T1 to T3 described above), the polythiol compound (B1) may also contain a compound (hereinafter also referred to as compound (S1)) in which at least one of the three or more thiol groups in the compound having three or more thiol groups is replaced with a group represented by the following formula (S1). This further promotes the polymerization reaction.

[0074] [Chemical Formula 3] In formula (S1), Indicates the bonding location.

[0075] For a polythiol compound (B1) containing a compound having three or more thiol groups (e.g., at least one of the polythiols T1 to T3 described above) and the compound (S1) described above, when the peak area is determined by high performance liquid chromatography, the peak area of ​​the compound (S1) is preferably 0.01 to 3.0 relative to the peak area 100 of the compound containing three or more thiol groups, more preferably 0.01 to 1.5.

[0076] When the peak area of ​​the above compound (S1) is 0.01 or more relative to the peak area 100 of the compound containing 3 or more thiol groups, the polymerization reaction can be further promoted.

[0077] When the peak area of ​​the above compound (S1) is less than 3.0 relative to the peak area of ​​100 of compounds containing 3 or more thiol groups, the polymerization reaction exhibits excellent controllability.

[0078] In the polymerizable composition disclosed herein, the total content of the polyisocyanate 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, relative to the total amount of the polymerizable composition.

[0079] The upper limit of the total content of polyisocyanate compound (A) and active hydrogen compound (B) is, for example, 98% by mass or less relative to the total amount of the polymerizable composition.

[0080] <Nitrogen-containing compounds (C)> The polymerizable composition disclosed herein contains at least one nitrogen-containing compound (C), said nitrogen-containing compound (C) being at least one of a nitrogen-containing aromatic heterocyclic compound and a tertiary amine compound.

[0081] Nitrogen-containing compounds (C) can function as curing catalysts.

[0082] Nitrogen-containing compounds (C) help to suppress turbidity and ripples in the resin obtained by curing polymeric compositions.

[0083] There are no particular restrictions on nitrogen-containing aromatic heterocyclic compounds (C) that are nitrogen-containing compounds, but compounds represented by the following formula (1) are preferred.

[0084] There are no particular restrictions on the tertiary amine compounds that are nitrogen-containing compounds (C), but compounds represented by the following formula (2) are preferred.

[0085] The nitrogen-containing compound (C) preferably includes at least one of the compounds represented by formula (1) and the compounds represented by formula (2).

[0086] (The compound represented by formula (1)) The compound represented by formula (1) is described below.

[0087] The compound represented by formula (1) is included in the concept of nitrogen-containing aromatic heterocyclic compounds.

[0088] [Chemical Formula 4] In formula (1), each of the m R1s independently represents a straight-chain alkyl group with 1 to 20 carbon atoms, a branched alkyl group with 3 to 20 carbon atoms, a cycloalkyl group with 3 to 20 carbon atoms, or a halogen atom, Q represents a carbon atom or a nitrogen atom, and m represents an integer from 0 to 5.

[0089] In formula (1), each of the m R1s independently represents a straight-chain alkyl group with 1 to 20 carbon atoms, a branched alkyl group with 3 to 20 carbon atoms, a cycloalkyl group with 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 from 0 to 5.

[0090] In equation (1), m is preferably an integer from 0 to 3, and more preferably an integer from 1 to 3.

[0091] In formula (1), the straight-chain alkyl group with 1 to 20 carbon atoms represented by R1 can be methyl, ethyl, n-propyl, n-butyl, pentyl, hexyl, heptyl, n-octyl, nonyl, decyl, dodecyl, etc.

[0092] In formula (1), branched alkyl groups with 3 to 20 carbon atoms represented by R1 can be represented by isopropyl, isobutyl, tert-butyl, isopentyl, isooctyl, 2-ethylhexyl, 2-propylpentyl, isodecyl, etc.

[0093] In formula (1), cycloalkyl groups with 3 to 20 carbon atoms represented by R1 can be cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, etc.

[0094] In formula (1), R1 is preferably a straight-chain alkyl or halogen atom with 1 to 20 carbon atoms, and more preferably a straight-chain alkyl or chlorine atom with 1 to 3 carbon atoms.

[0095] The compound represented by formula (1) is preferably selected from at least one of the group consisting of 2-methylpyrazine, pyridine, α-methylpyridine, β-methylpyridine, γ-methylpyridine, 2,6-dimethylpyridine, 3,5-dimethylpyridine, 2,4,6-trimethylpyridine, 3-chloropyridine, 2-ethylpyridine, and 3-ethylpyridine.

[0096] (The compound represented by formula (2)) The compound represented by formula (2) is described below.

[0097] The compound represented by formula (2) is included in the concept of tertiary amine compounds.

[0098] [Chemical Formula 5] In formula (2), R2, R3 and R4 each independently represent a straight-chain alkyl group with 3 to 20 carbon atoms, a branched alkyl group with 3 to 20 carbon atoms, a cycloalkyl group with 3 to 20 carbon atoms, or an allyl group. R2 and R3 can bond to each other to form a ring.

[0099] In formula (2), R2, R3 and R4 are each preferably straight-chain alkyl with 3 to 20 carbon atoms, more preferably straight-chain alkyl with 3 to 10 carbon atoms, and particularly preferably straight-chain alkyl with 5 to 10 carbon atoms.

[0100] Examples of straight-chain alkyl groups with 3 to 20 carbon atoms, represented by R2, R3, or R4, include n-propyl, n-butyl, pentyl, hexyl, heptyl, n-octyl, nonyl, decyl, and dodecyl.

[0101] R2 and R3 can bond together to form a ring.

[0102] That is, the compound represented by formula (2) can also be a cyclic amine compound with R2 and R3 bonded to each other to form a ring.

[0103] Examples of the aforementioned cyclic amine compounds include 1-propylpiperidine, 1-butylpiperidine, 1-cyclohexylpiperidine, 1-butylpyrrolidine, and 1-cyclohexylpyrrolidine.

[0104] The compound represented by formula (2) is preferably at least one selected from the group consisting of triallylamine and trioctylamine.

[0105] The content of nitrogen-containing compound (C) in the polymerizable composition (i.e., the total content of nitrogen-containing aromatic heterocyclic tertiary amine compounds; for example, the total content of compounds represented by formula (1) and compounds represented by formula (2)) is preferably 0.01% to 1% by mass, more preferably 0.01% to 0.5% by mass, relative to the total content of polyisocyanate compound (A) and active hydrogen compound (B).

[0106] The content of nitrogen-containing compounds (C) in the polymerizable composition (i.e., the total content of nitrogen-containing aromatic heterocyclic compounds and tertiary amine compounds; for example, the total content of compounds represented by formula (1) and compounds represented by formula (2)) is preferably 0.01% to 1% by mass, more preferably 0.01% to 0.5% by mass, relative to the total amount of the polymerizable composition.

[0107] Regarding the content of nitrogen-containing compounds (C) in polymeric compositions, please refer to International Publication Nos. 2021 / 153631 and 2021 / 153632.

[0108] The polymerizable compositions disclosed herein may also contain other compounds besides the nitrogen-containing compound (C) described above as curing catalysts.

[0109] The proportion of nitrogen-containing compound (C) in the curing catalyst is preferably 50% to 100% by mass, more preferably 60% to 100% by mass, even more preferably 80% to 100% by mass, and even more preferably 90% to 100% by mass.

[0110] <Water> The polymeric composition disclosed herein contains water.

[0111] The water content is less than 1900 ppm by mass relative to the total amount of the polymeric composition.

[0112] As mentioned above, when a nitrogen-containing compound (C) is used as a curing catalyst in a polymeric composition containing a polyisocyanate compound (A) and an active hydrogen compound (B), devitrification in the resulting resin is sometimes not suppressed.

[0113] In contrast, in the polymeric composition of this disclosure, devitrification in the resulting resin can be suppressed by keeping the water content below 1900 ppm by mass relative to the total amount of the polymeric composition.

[0114] From the viewpoint of more effectively obtaining the effect of suppressing devitrification, the water content is preferably 1500 ppm by mass or less, more preferably 1100 ppm by mass or less, relative to the total amount of the polymerizable composition.

[0115] From the viewpoint of further improving the manufacturing adaptability of the polythiol composition and / or the polymerizability of the monomers, the water content is preferably 10 ppm by mass or more relative to the total amount of the polymerizable composition, more preferably 100 ppm by mass or more, and even more preferably 200 ppm by mass or more.

[0116] <Other Ingredients> The polymeric compositions disclosed herein may contain other components besides those described above.

[0117] Other components include internal mold release agents, resin modifiers, chain extenders, crosslinking agents, free radical scavengers, light stabilizers, ultraviolet absorbers, antioxidants, oil-soluble dyes, fillers, adhesion enhancers, antibacterial agents, antistatic agents, dyes, fluorescent whitening agents, fluorescent pigments, inorganic pigments, and bluing agents.

[0118] Acidic phosphate esters can be used as internal mold release agents. Examples of acidic phosphate esters include monophosphate esters and diphosphate esters, which can be used alone or in combination of two or more.

[0119] In addition, the polymerizable composition of this disclosure may further comprise a prepolymer having polymerizable functional groups as a polymer (i.e., reactant) of a polyisocyanate compound (A) and an active hydrogen compound (B).

[0120] Examples of polymerizable functional groups include, for example, the isocyanate group contained in the polyisocyanate compound (A), and the active hydrogen group (e.g., mercapto) contained in the active hydrogen compound (B).

[0121] Regarding prepolymers, for example, see International Publication No. 2021 / 153631 and International Publication No. 2021 / 153632.

[0122] There are no particular limitations on the method of manufacturing the polymeric composition described above, and known methods of mixing the above-described components may be suitably applied.

[0123] An example of a method for manufacturing the polymeric composition of this disclosure (hereinafter also referred to as method A) is described below, but the method for manufacturing the polymeric composition of this disclosure is not limited to method A.

[0124] [An example of a method for manufacturing a polymeric composition (method A)] Method A includes a step (hereinafter also referred to as the mixing step) of mixing a raw material composition (BX), a polyisocyanate compound (A), and a nitrogen-containing compound (C), wherein the raw material composition (BX) contains an active hydrogen compound (B) and water, and the water content is less than 3800 ppm by mass relative to the total amount of the raw material composition (BX).

[0125] In the mixing process, other components besides those mentioned above may also be mixed.

[0126] Method A may also include other steps besides the mixing step.

[0127] In the mixing step of method A, the raw material composition (BX) is used.

[0128] The raw material composition (BX) is a composition containing an active hydrogen compound (B) and water, wherein the water content is less than 3800 ppm by mass relative to the total amount of the raw material composition (BX).

[0129] The water content in the raw material composition (BX) is preferably 2200 ppm by mass or less, more preferably 1000 ppm by mass or less.

[0130] The water content in the 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.

[0131] In method A, there are no particular restrictions on the order in which the raw materials (i.e., the raw material composition (BX), the polyisocyanate compound (A), and the nitrogen-containing compound (C)) are mixed (i.e., the order in which they are added to the container used for mixing).

[0132] For example, the total amount of raw materials can be added into the container at once and mixed to obtain a polymerizable composition, or the raw materials can be added into the container little by little and mixed to obtain a polymerizable composition.

[0133] Alternatively, a portion of the total amount of raw materials can be added to a container first to form a prepolymer with polymerizable functional groups, which is a polymer of polyisocyanate compound (A) and active hydrogen compound (B). Then, the remaining portion of the raw materials is added to obtain a polymerizable composition containing polyisocyanate compound (A), active hydrogen compound (B), nitrogen-containing compound (C), prepolymer with polymerizable functional groups, and water.

[0134] [Resin, Molded Body] The resin in this disclosure is a cured product of the polymeric composition described above.

[0135] The molded body of this disclosure contains the resin of this disclosure.

[0136] That is, the resin of this disclosure can be manufactured by curing the polymeric composition of this disclosure described above, specifically by polymerizing and curing the monomers in the polymeric composition of this disclosure.

[0137] As a method for polymerizing monomers in the polymerizable composition of this disclosure, casting polymerization can be cited as an example. By casting polymerization, a molded body of this disclosure containing the resin of this disclosure (i.e., a cured polymerizable composition of this disclosure) can be obtained.

[0138] In casting polymerization, firstly, the polymerizable composition, as exemplified in this disclosure, is injected between a pair of molding dies held by gaskets or tapes. At this point, degassing, filtration, etc., may be performed as needed.

[0139] Next, the monomers in the composition injected into the molding die are polymerized, thereby curing the composition in the molding die to obtain a cured product. Then, the cured product is removed from the molding die to obtain the cured product.

[0140] The polymerization of the aforementioned monomers can be carried out by heating the polymerizable composition of this disclosure. This heating can be carried out, for example, using a heating device equipped with a mechanism for heating the object in an oven, water, or similar medium.

[0141] The polymerization conditions (e.g., polymerization temperature, polymerization time, etc.) used to polymerize the monomers in the polymerizable compositions of this disclosure can be suitably set taking into account the composition of the composition, the type and amount of monomers in the composition, the type and amount of polymerization catalyst in the composition, the shape of the mold, etc.

[0142] Examples of polymerization temperatures include -50℃ to 150℃ and 10℃ to 150℃.

[0143] As for the aggregation time, examples include 1 hour to 200 hours, 1 hour to 80 hours, etc.

[0144] The resin or molded body containing the resin in this disclosure may also be obtained by annealing or other treatments after polymerization of the monomer.

[0145] Examples of annealing temperatures include 50℃~150℃, 90℃~140℃, and 100℃~130℃.

[0146] [Optical Materials] The optical material of this disclosure includes the resin described above.

[0147] The optical materials disclosed herein can be manufactured, for example, by the aforementioned casting polymerization.

[0148] The optical material of this disclosure may be formed from the resin of this disclosure, or may contain the resin of this disclosure and other elements.

[0149] Other elements include other components, coatings provided for the resin used in this disclosure, etc.

[0150] Examples of optical materials used in this disclosure include lenses (e.g., spectacle lenses, camera lenses, polarizing lenses, etc.) and light-emitting diodes (LEDs).

[0151] 〔lens〕 The lens in this disclosure is an example of the optical material of this disclosure, including the resin described above.

[0152] The lens of this disclosure can be manufactured, for example, by the aforementioned casting polymerization.

[0153] The lens of this disclosure may be formed from the resin of this disclosure, or may contain the resin of this disclosure and other elements.

[0154] Other elements include other components, coatings provided for the resin used in this disclosure, etc.

[0155] Examples of lenses used in this disclosure include eyeglass lenses, camera lenses, and polarizing lenses.

[0156] The following description, as an example of a lens used in this disclosure, illustrates an eyeglass lens.

[0157] The eyeglass lens comprises resin formed into the desired lens shape as described in this disclosure.

[0158] The eyeglass lens preferably also includes a coating disposed on one or both sides of the resin.

[0159] As a coating, examples include primers, hard coatings, anti-reflective layers, anti-fog coatings, anti-fog layers, and waterproof layers. These coatings can be used individually or in multiple layers.

[0160] When applying a coating to both sides of a cured material, the same coating can be applied to each side, or different coatings can be applied.

[0161] The composition of the coating can be appropriately selected according to the purpose.

[0162] As components of the coating, examples 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, antistatic agents, etc.

[0163] Regarding eyeglass lenses and coatings, for example, reference may be made to known documents such as Japanese Patent Application Publication No. 2002-194083 and International Publication No. 2017 / 047745.

[0164] Example The following are examples of embodiments of this disclosure, but this disclosure is not limited to the following embodiments.

[0165] It should be noted that unless otherwise specified, "parts" and "%" are based on mass.

[0166] [Examples 1-3, and Comparative Examples 1 and 2] <Preparation of polythiol compounds (B1-1)> The production of a polythiol compound (B1-1) containing polythiol T1 as the main component is carried out. Here, the polythiol compound (B1-1) is an example of an active hydrogen compound (B). Details are shown below.

[0167] 124.6 parts by mass of 2-mercaptoethanol and 18.3 parts by mass of degassed water were charged into a reactor. After 40 minutes at 12°C–35°C, 101.5 parts by mass of a 32% sodium hydroxide aqueous solution were added dropwise. Then, after 4.5 hours at 29°C–36°C, 73.6 parts by mass of epichlorohydrin were added dropwise, followed by stirring for another 40 minutes. The result was the formation of 1,3-bis(2-hydroxyethylthio)-2-propanol in the reactor. This formation was confirmed using NMR data.

[0168] Next, 331.5 parts by mass of 35.5% hydrochloric acid were added to the reactor, followed by 183.8 parts by mass of thiourea with a purity of 99.90%. The mixture was then stirred under reflux at 110°C for 3 hours to carry out the thiourea onium salting reaction. Next, the liquid in the reactor was cooled to 45°C, and 320.5 parts by mass of toluene were added. The resulting liquid was cooled to 31°C, and then 243.1 parts by mass of 25% ammonia solution were added at 31°C to 41°C for 44 minutes. The mixture was then stirred at 54°C to 62°C for 3 hours to carry out the hydrolysis reaction. The result was a toluene solution of a polythiol compound (B1-1) with polythiol T1 (i.e., 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane) as the main component. The toluene solution was acid-washed for 1 hour at 35°C–43°C using 162.8 parts by mass of 35.5% hydrochloric acid. The acid-washed toluene solution was then washed twice at 35°C–45°C using 174.1 parts by mass of degassed water for 30 minutes. The toluene solution after the second water-based wash was then washed for 30 minutes using 162.1 parts by mass of 0.1% ammonia. The ammonia-based toluene solution was then washed twice at 35°C–45°C using 174.2 parts by mass of degassed water for 30 minutes. Next, toluene and trace amounts of water were removed under reduced pressure by heating. The solution was then processed by silica gel column chromatography, followed by reduced pressure filtration using a 1.2 μm PTFE membrane filter to obtain a polythiol compound (B1-1) (205.0 parts by mass) containing polythiol T1 as the main component.

[0169] <Preparation of the raw material composition (BX)> The polythiol compound (B1-1) obtained as described above is mixed with water to obtain the raw material composition (BX).

[0170] The mixing ratio of polythiol compound (B1-1) to water was adjusted so that the water content (mass%) relative to the total amount of the raw material composition (BX) was the value shown in Table 1.

[0171] Here, the water content relative to the total amount of the raw material composition (BX) was determined using a Karl Fischer moisture meter (MKC-710 manufactured by Kyoto Electronics Industry Co., Ltd.).

[0172] <Preparation of Polymer Compositions> 52 parts by weight of isophthalene diisocyanate (hereinafter also referred to as "NCO1"), which is a polyisocyanate compound (A), were mixed with VIOSORB583 (manufactured by Kyodo Pharmaceutical Co., Ltd.) (1.0 part by weight). Then, 3,5-dimethylpyridine (0.03 parts by weight), which is a nitrogen-containing compound (C), and JP-506H (manufactured by Jōhoku Chemical Industry Co., Ltd.; acidic phosphate ester) (0.075 parts by weight), which is an internal mold release agent, were mixed in at 20°C to prepare a mixture. The resulting mixture was degassed at 600 Pa for 1 hour.

[0173] Next, the raw material composition (BX), which had been degassed at 600 Pa for 1 hour, was added to the composition at an addition amount of 47% by mass relative to the total composition, and the mixture was mixed at 20°C to obtain a polymerizable composition.

[0174] The water content (mass ppm) relative to the total amount of the obtained polymeric composition was determined using a Karl Fischer moisture meter (MKC-710, Kyoto Electronics Industry Co., Ltd.), and the results are shown in Table 1.

[0175] <Manufacturing of Resin Molded Components> Next, the above polymeric composition was subjected to degassing at 600 Pa for 10 minutes.

[0176] The degassed polymeric composition was filtered using a 1μm Teflon (registered trademark) filter. The filtrate was then injected between a pair of glass molds secured with tape. The molds were then placed in an oven at 30°C. The oven temperature was then increased from 30°C to 70°C over 1.5 hours, followed by an increase to 120°C over 0.5 hours, maintained at 120°C for 1 hour, and then decreased to 70°C over 1 hour. This process polymerized the monomers in the polymeric composition (i.e., NCO1 and the polythiol compound (B1-1)), forming a resin-containing molded body (i.e., the cured polymeric composition) between the glass molds.

[0177] Next, the oven is cooled. After cooling, a pair of glass molds are removed from the oven, and then the resin-containing molded body (hereinafter referred to as the resin molded body) is removed from the pair of glass molds.

[0178] The obtained resin molded body was annealed at 120°C for 1 hour to obtain a circular flat lens with a thickness of 9.0 mm and a diameter of 75 mm.

[0179] <Lens Measurement and Evaluation> The following evaluation is made for the above-mentioned circular flat lens (i.e., the annealed resin molded body).

[0180] The results are shown in Table 1.

[0181] It should be noted that in Table 1, "B1-1" refers to polythiol compounds (B1-1).

[0182] (bubble) The lens is visually inspected, and the bubbles in the lens are evaluated according to the following evaluation criteria.

[0183] In the following evaluation criteria, the grade that suppresses bubble formation to the greatest extent is A.

[0184] -Evaluation Criteria for Bubbles- A. No bubbles were detected throughout the entire lens.

[0185] B. The formation of bubbles was confirmed in a portion of the lens.

[0186] C. The formation of the bubble was confirmed by examining the entire lens.

[0187] (Waves) The lens is visually observed, and the ridges in the lens are evaluated according to the following evaluation criteria.

[0188] In the following evaluation criteria, the level that suppresses the generation of ridges to the greatest extent is A.

[0189] -Evaluation Criteria for Corrugations- A. No ridges were detected throughout the entire lens.

[0190] B. The generation of ridges was confirmed in a portion of the lens.

[0191] C. The generation of the ridge was confirmed by examining the entire lens.

[0192] (Opacity loss) For the lens, light from a light source (HAYASHI-REPIC Luminar Ace LA-150A) is allowed to pass through in a dark environment. An image of the light passing through the lens is captured and processed in an image processing device (Ube Information Systems, Inc.) to adjust the image's density. The density of the processed image is then quantified for each pixel, and the average density value of each pixel is calculated to determine the lens's deflection.

[0193] Based on the obtained devitrification, the devitrification of the lens is evaluated according to the following evaluation criteria.

[0194] In the following evaluation criteria, the grade that suppresses lens de-reflection to the greatest extent is A.

[0195] -Evaluation Criteria for De-opaqueness- A: Devitrification is less than 35.

[0196] B: Devitrification is 35 or higher and less than 50.

[0197] C: Devitrification is above 50.

[0198] [Example 4, and Comparative Examples 3 and 4] <Preparation of polythiol compounds (B1-1)> The polythiol compound (B1-1) was prepared by operating in the same manner as in Example 1.

[0199] <Preparation of polythiol compounds (B1-2)> The production of a polythiol compound (B1-2) comprising polythiol T3 (i.e., pentaerythritol tetra(3-mercaptopropionate)) as the main component is carried out. Here, the polythiol compound (B1-2) is an example of an active hydrogen compound (B). Details are shown below.

[0200] A mixture was prepared by adding 136.9 parts by mass of pentaerythritol (99.5% purity), 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 to a four-necked reaction flask equipped with a stirrer, a Dean-Stark tube, a nitrogen purging tube, and a thermometer. Here, the molar ratio of 3-mercaptopropionic acid to pentaerythritol was 3.80.

[0201] For the above mixture, heating was initiated using an oil bath. 120 minutes after the start of heating, when the internal temperature reached 97°C, reflux was initiated (oil bath temperature 113°C). After reflux began, the reaction was carried out for 7 hours (internal temperature 97~121°C).

[0202] During the above reaction, water generated by the side reaction is continuously discharged from the system under reflux. The amount of water discharged from the system is 93.2% relative to the theoretically generated water.

[0203] The reaction solution after the above reaction was cooled, and then alkali washing and water washing were performed in sequence.

[0204] Toluene and trace amounts of water were removed from the reaction solution after washing with water under heating and reduced pressure. The remaining reaction solution was filtered using a PTFE membrane filter to obtain 462.3 parts by mass of a polythiol compound (B1-2) containing polythiol T3 as the main component.

[0205] <Preparation of the raw material composition (BX)> The polythiol compounds (B1-1) and (B1-2) obtained as described above are mixed with water to obtain the raw material composition (BX).

[0206] The mixing ratio of polythiol compound (B1-1), polythiol compound (B1-2) and water was adjusted to a mass ratio of 1:1 [polythiol compound (B1-1): polythiol compound (B1-2)] and the water content (mass%) relative to the total amount of the raw material composition (BX) was adjusted to the values ​​shown in Table 1.

[0207] Here, the water content relative to the total amount of the raw material composition (BX) was determined using a Karl Fischer moisture meter (MKC-710 manufactured by Kyoto Electronics Industry Co., Ltd.).

[0208] <Preparation of Polymer Compositions> A mixture of 2,5-bis(isocyanate methyl)bicyclo-[2.2.1]-heptane and 2,6-bis(isocyanate methyl)bicyclo-[2.2.1]-heptane (hereinafter also referred to as "NCO2") (50.6 parts by mass) as polyisocyanate compound (A) was mixed with ultraviolet absorber VIOSORB583 (manufactured by Kyodo Pharmaceutical Co., Ltd.) (1.0 parts by mass). Then, at 20°C, 3,5-dimethylpyridine (0.20 parts by mass) as nitrogen-containing compound (C) and JP-506H (manufactured by Jōhoku Chemical Industry Co., Ltd.; acidic phosphate ester) (0.10 parts by mass) as internal mold release agent were added to prepare a mixture. The resulting mixture was degassed at 600 Pa for 1 hour.

[0209] Next, the raw material composition (BX), which had been degassed at 600 Pa for 1 hour, was added to the composition at an addition amount of 49% by mass relative to the total composition, and the mixture was mixed at 20°C to obtain a polymerizable composition.

[0210] The water content (mass ppm) relative to the total amount of the obtained polymeric composition was determined using a Karl Fischer moisture meter (MKC-710, Kyoto Electronics Industry Co., Ltd.), and the results are shown in Table 1.

[0211] <Manufacturing of Resin Molded Components> Using the above-described polymeric composition, a resin molded article was obtained by operating in the same manner as the resin molded article in Example 1.

[0212] The obtained resin molded body was annealed at 120°C for 1 hour to obtain a circular flat lens with a thickness of 9.0 mm and a diameter of 75 mm.

[0213] <Lens Measurement and Evaluation> The same evaluations as those in Example 1 were performed on the above-mentioned circular flat lens (i.e., the annealed resin molded body).

[0214] The results are shown in Table 1.

[0215] It should be noted that in Table 1, "B1-1" refers to polythiol compound (B1-1), and "B1-2" refers to polythiol compound (B1-2).

[0216] [Table 1] As shown in Table 1, in Examples 1 to 3, which used a polymeric composition containing a polyisocyanate compound (A), an active hydrogen compound (B), a nitrogen-containing compound (C), and water, and in which the water content was less than 1900 ppm by mass relative to the total amount of the polymeric composition, bubbles, ripples, and devitrification were suppressed in the resulting lenses (i.e., resin molded bodies).

[0217] Compared to Examples 1-3, in Comparative Example 1, which used a polymeric composition containing a polyisocyanate compound (A), an active hydrogen compound (B), a nitrogen-containing compound (C), and water, and in which the water content was greater than 1900 ppm by mass relative to the total amount of the polymeric composition, devitrification was not suppressed in the resulting lens (i.e., the resin molded body).

[0218] The full disclosure of Japanese Patent Application 2023-122891, filed on July 27, 2023, is incorporated herein by reference.

[0219] All documents, patent applications and technical standards described in this specification are incorporated herein by reference to the extent that each document, patent application and technical standard is incorporated by reference to the extent that it is specifically and separately described.

Claims

1. A polymerizable composition comprising: Polyisocyanate compound (A); Active hydrogen compounds (B); Nitrogen-containing compound (C), wherein the nitrogen-containing compound (C) is at least one of a nitrogen-containing aromatic heterocyclic compound and a tertiary amine compound; and water, The water content is less than 1900 ppm by mass relative to the total amount of the polymeric composition.

2. The polymeric composition of claim 1, wherein, The nitrogen-containing compound (C) comprises at least one of the compounds represented by formula (1) and the compounds represented by formula (2). [Chemical Formula 1] In formula (1), each of the m R1s independently represents a straight-chain alkyl group with 1 to 20 carbon atoms, a branched alkyl group with 3 to 20 carbon atoms, a cycloalkyl group with 3 to 20 carbon atoms, or a halogen atom; Q represents a carbon atom or a nitrogen atom; and m represents an integer from 0 to 5. In formula (2), R2, R3 and R4 each independently represent a straight-chain alkyl group with 3 to 20 carbon atoms, a branched alkyl group with 3 to 20 carbon atoms, a cycloalkyl group with 3 to 20 carbon atoms, or an allyl group. R2 and R3 can bond to each other to form a ring.

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

4. The polymerizable composition of claim 1, wherein, The polyisocyanate compound (A) comprises at least one selected from the group consisting of pentamethylene diisocyanate, hexamethylene diisocyanate, phenylene 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, toluene diisocyanate, 4,4'-diphenylmethane diisocyanate, and phenyl diisocyanate.

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

6. The polymerizable composition of claim 5, wherein, The polythiol compound (B1) comprises, selected from 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(2-mercaptoacetate), etc. At least one of the following groups: (mercaptomethyl)-1,4-dithiacyclohexane, bis(2-mercaptoethyl) sulfide, 1,1,3,3-tetra(mercaptomethylthio)propane, 4,6-bis(mercaptomethylthio)-1,3-dithiacyclohexane, 2-(2,2-bis(mercaptomethylthio)ethyl)-1,3-dithiacyclobutane, 1,1,2,2-tetra(mercaptomethylthio)ethane, 3-mercaptomethyl-1,5-dimercapto-2,4-dithiapentane, and tri(mercaptomethylthio)methane.

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

8. A method for manufacturing a polymeric composition, wherein the method is for manufacturing the polymeric composition of claim 1. The manufacturing method includes a step of mixing a raw material composition (BX), the polyisocyanate compound (A), and the nitrogen-containing compound (C), wherein the raw material composition (BX) contains the active hydrogen compound (B) and water, and the water content is less than 3800 ppm by mass relative to the total amount of the raw material composition (BX).

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

10. A molded article comprising the resin of claim 9.

11. An optical material comprising the resin of claim 9.

12. A lens comprising the resin of claim 9.

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