Isocyanate composition, optical lens comprising same, and isocyanate composition storage method using same

Abstract

The present invention relates to an isocyanate composition, an optical lens comprising same, and an isocyanate composition storage method using same.

Description

Isocyanate composition, optical lens containing the same, and method for storing the isocyanate composition using the same

[0001] The present invention relates to an isocyanate composition, an optical lens comprising the same, and a method for storing an isocyanate composition using the same.

[0002]

[0003] Isocyanate compounds are raw materials for polyurethane, widely used in coatings, adhesives, paints, foams, and optical materials. Polyurethanes used in fields requiring superior appearance properties, particularly optical applications requiring transparency, require minimal discoloration. To achieve this, it is crucial that not only does the polyurethane polymer resist discoloration during the polyurethane reaction, but also that the raw isocyanate compounds themselves, particularly those with higher than difunctionality, remain discolored.

[0004] However, since isocyanate compounds are highly reactive, they are easily oxidized by oxygen in the air during the storage process, or they form self-polymers, causing deterioration or discoloration. There was also a problem of discoloration or clouding occurring in optical products such as urethane lenses that applied them.

[0005] To this end, various methods have been studied and proposed to suppress discoloration in isocyanate compounds and products manufactured using them, such as sealing with nitrogen gas to block air and storing in a refrigerator, or storing by adding additives such as ultraviolet absorbers.

[0006] However, in order to use an isocyanate compound, it must be moved from the storage location to the atmospheric environment. During this process, the isocyanate compound may discolor or become cloudy depending on changes in the moisture content or temperature of the atmosphere. If an isocyanate compound that has discolored or become cloudy is used to manufacture optical lenses, there is a problem that the clarity is reduced, resulting in a deterioration in quality.

[0007] Additionally, there are difficulties in ensuring long-term storage stability of isocyanate compounds.

[0008]

[0009] The present invention has been devised to overcome the above-described problems, and provides an isocyanate composition having excellent storage stability even when the isocyanate compound is stored for a long period of time by including a specific compound, an optical lens including the same, and a method for storing the isocyanate composition using the same.

[0010] In addition, the present invention aims to provide an isocyanate composition with improved clarity, an optical lens including the same, and a method for storing the isocyanate composition using the same.

[0011] In addition, the present invention aims to provide an isocyanate composition capable of producing a polyurethane resin having excellent thermal stability using the isocyanate composition, an optical lens including the same, and a method for storing the isocyanate composition using the same.

[0012] In addition, the present invention aims to provide an isocyanate composition capable of manufacturing a transparent optical material (e.g., an optical lens) that is not only less likely to cause defects but also has improved yellowness (YI), an optical lens comprising the same, and a method for storing an isocyanate composition using the same.

[0013] In addition, the present invention aims to provide an isocyanate composition having excellent impact resistance and strength, an optical lens including the same, and a method for storing the isocyanate composition using the same.

[0014]

[0015] To solve the above-described problem, the isocyanate composition of the present invention may include a diisocyanate compound and a compound having a retention time of 10.5 to 12.5 minutes when measured under the measurement conditions of the following gas chromatography mass spectrometry.

[0016] <Measurement conditions for gas chromatography mass spectrometry>

[0017] Column; DB-17MS (inner diameter 0.25 mm × length 30 m, film 0.25 μm)

[0018] Injection volume; 1 μl, Split ratio 10:1

[0019] Injection temperature; 280℃

[0020] Oven temperature: Maintain at 100°C for 1 minute, increase at 10.0°C / min from 100°C to 165°C, maintain for 3 minutes after reaching 165°C, increase at 3.0°C / min from 165°C to 177°C, increase at 20.0°C / min from 177°C to 300°C, maintain for 15 minutes after reaching 300°C.

[0021] As a preferred embodiment of the present invention, when measured under the measurement conditions of the gas chromatography mass spectrometry, a compound having a retention time of 10.5 to 12.5 minutes may have a mass-to-charge ratio (m / z) of 148 to 150, 119 to 121, 106 to 108, 93 to 95, 76 to 78, and 64 to 66.

[0022] As a preferred embodiment of the present invention, when measured under the measurement conditions of the gas chromatography mass spectrometry, the compound having a retention time of 10.5 to 12.5 minutes may be a compound represented by the following chemical formula 1.

[0023] [Chemical Formula 1]

[0024]

[0025] In the above chemical formula 1, B1 is -CH2-, -CH2CH2-, -CH2CH2CH2-, -CH2CH2CH2CH2-, or -CH2CH2CH2CH2CH2-, and R1 is -H, a straight-chain alkyl group of C1 to C12, or a branched alkyl group of C3 to C12.

[0026] As a preferred embodiment of the present invention, the isocyanate composition of the present invention can satisfy the following condition (1).

[0027] (1) 0.1 ppm ≤ A ≤ 60 ppm

[0028] In the above condition (1), A represents the content (ppm) of a compound having a retention time of 10.5 to 12.5 minutes when measured under the measurement conditions of the gas chromatography mass spectrometry with respect to the total weight of the isocyanate composition.

[0029] As a preferred embodiment of the present invention, the isocyanate composition of the present invention may further include a compound represented by the following chemical formula 2.

[0030] [Chemical Formula 2]

[0031]

[0032] In the above chemical formula 2, B2 is -CH2-, -CH2CH2-, -CH2CH2CH2-, -CH2CH2CH2CH2-, or -CH2CH2CH2CH2CH2-.

[0033] As a preferred embodiment of the present invention, the isocyanate composition of the present invention can satisfy the following condition (2).

[0034] (2) 0.1 ppm ≤ B ≤ 100 ppm

[0035] In the above condition (2), B represents the content (ppm) of the compound represented by the above chemical formula 2 with respect to the total weight of the isocyanate composition.

[0036] As a preferred embodiment of the present invention, the isocyanate composition of the present invention may include a compound represented by Chemical Formula 2 and a compound having a retention time of 10.5 to 12.5 minutes when measured under the measurement conditions of the gas chromatography mass spectrometry, in a weight ratio of 1:0.05 to 0.6.

[0037] As a preferred embodiment of the present invention, the diisocyanate compound may include at least one selected from 1,4-tetramethylene diisocyanate, 1,5-pentamethylene diisocyanate, 1,6-hexamethylene diisocyanate, 1,3-cyclohexylene diisocyanate, 1,4-cyclohexylene diisocyanate, isophorone diisocyanate, norbornene diisocyanate, methylenediphenyl diisocyanate, methylenedicyclohexyl isocyanate, toluene diisocyanate, m-xylylene diisocyanate, p-xylylene diisocyanate, and o-xylylene diisocyanate.

[0038] In a preferred embodiment of the present invention, the diisocyanate compound may be m-xylylene diisocyanate.

[0039] As a preferred embodiment of the present invention, the compound represented by the chemical formula 1 may be a compound represented by the following chemical formula 1-1.

[0040] [Chemical Formula 1-1]

[0041]

[0042] In the above chemical formula 1-1, B1 is -CH2-, -CH2CH2- or -CH2CH2CH2-, and R1 is a straight-chain alkyl group of C1 to C12.

[0043] As a preferred embodiment of the present invention, the compound represented by the chemical formula 2 may be a compound represented by the following chemical formula 2-1.

[0044] [Chemical Formula 2-1]

[0045]

[0046] In the above chemical formula 2-1, B2 is -CH2-, -CH2CH2- or -CH2CH2CH2-.

[0047] As a preferred embodiment of the present invention, the isocyanate composition of the present invention can satisfy the following condition (3).

[0048] (3) 0% ≤ D - C ≤ 2.0%

[0049] In the above condition (3), C represents the haze value of the isocyanate composition, and D represents the haze value measured after storing the isocyanate composition under conditions of a temperature of 20°C or lower and a humidity of 1%RH or lower for 160 to 200 days.

[0050] Meanwhile, the method for storing an isocyanate composition of the present invention may include a first step of preparing an isocyanate composition including a diisocyanate compound and a compound having a retention time of 10.5 to 12.5 minutes when measured under the measurement conditions of gas chromatography mass spectrometry below, and a second step of storing the prepared isocyanate composition under conditions of a nitrogen-substituted atmosphere, a temperature of 20°C or lower, and a humidity of 1% RH or lower.

[0051] <Measurement conditions for gas chromatography mass spectrometry>

[0052] Column; DB-17MS (inner diameter 0.25 mm × length 30 m, film 0.25 μm)

[0053] Injection volume; 1 μl, Split ratio 10:1

[0054] Injection temperature; 280℃

[0055] Oven temperature: Maintain at 100°C for 1 minute, increase at 10.0°C / min from 100°C to 165°C, maintain for 3 minutes after reaching 165°C, increase at 3.0°C / min from 165°C to 177°C, increase at 20.0°C / min from 177°C to 300°C, maintain for 15 minutes after reaching 300°C.

[0056] As a preferred embodiment of the present invention, when measured under the measurement conditions of the gas chromatography mass spectrometry, the compound having a retention time of 10.5 to 12.5 minutes may be a compound represented by the following chemical formula 1.

[0057] [Chemical Formula 1]

[0058]

[0059] In the above chemical formula 1, B1 is -CH2-, -CH2CH2-, -CH2CH2CH2-, -CH2CH2CH2CH2-, or -CH2CH2CH2CH2CH2-, and R1 is -H, a straight-chain alkyl group of C1 to C12, or a branched alkyl group of C3 to C12.

[0060] As a preferred embodiment of the present invention, the isocyanate composition prepared in the first step can satisfy the following condition (1).

[0061] (1) 0.1 ppm ≤ A ≤ 60 ppm

[0062] In the above condition (1), A represents the content (ppm) of a compound having a retention time of 10.5 to 12.5 minutes when measured under the measurement conditions of the gas chromatography mass spectrometry with respect to the total weight of the isocyanate composition.

[0063] As a preferred embodiment of the present invention, the isocyanate composition prepared in the first step may further include a compound represented by the following chemical formula 2.

[0064] [Chemical Formula 2]

[0065]

[0066] In the above chemical formula 2, B2 is -CH2-, -CH2CH2-, -CH2CH2CH2-, -CH2CH2CH2CH2-, or -CH2CH2CH2CH2CH2-.

[0067] As a preferred embodiment of the present invention, the isocyanate composition of the present invention prepared in the first step can satisfy the following condition (2).

[0068] (2) 0.1 ppm ≤ B ≤ 100 ppm

[0069] In the above condition (2), B represents the content (ppm) of the compound represented by the above chemical formula 2 with respect to the total weight of the isocyanate composition.

[0070] As a preferred embodiment of the present invention, the second step may be to store the isocyanate composition under nitrogen-substituted atmosphere, at a temperature of 0 to 20°C and a humidity of 0.0001 to 1%RH.

[0071] Furthermore, the optical lens of the present invention may include the isocyanate composition of the present invention.

[0072] As a preferred embodiment of the present invention, the optical lens of the present invention may have a yellowness (YI) of 2.5 or less.

[0073] Meanwhile, the non-foam resin of the present invention may include the isocyanate composition of the present invention.

[0074] As a preferred embodiment of the present invention, the non-foam resin of the present invention may be used for a coating, an adhesive, a sealant, or an elastomer.

[0075]

[0076] The isocyanate composition of the present invention, the optical lens comprising the same, and the storage method of the isocyanate composition using the same not only have excellent storage stability, but also can improve clarity and yellowness (YI).

[0077]

[0078] Hereinafter, the present invention will be described in more detail.

[0079] Various methods have been studied and proposed to suppress discoloration in existing isocyanate compounds and products manufactured using them, such as sealing them with nitrogen gas to block air and storing them in a refrigerator, or storing them using additives such as ultraviolet absorbers. However, in order to use isocyanate compounds, they must be moved from their storage location to the open air. During this process, the isocyanate compounds may discolor or become cloudy depending on changes in the moisture content or temperature of the air. If discolored or cloudy isocyanate compounds are used to manufacture optical lenses, there is a problem of reduced clarity and deterioration in quality. In addition, it is difficult to ensure the long-term storage stability of isocyanate compounds.

[0080] Accordingly, the present invention not only has excellent storage stability by including a specific compound, but also improves clarity and yellowness (YI).

[0081]

[0082] The isocyanate composition of the present invention may include a diisocyanate compound and a compound having a retention time of 10.5 to 12.5 minutes, preferably 11.0 to 12.0 minutes, and more preferably 11.4 to 11.6 minutes, when measured under the measurement conditions of the following gas chromatography mass spectrometry.

[0083] <Measurement conditions for gas chromatography mass spectrometry>

[0084] Column; DB-17MS (inner diameter 0.25 mm × length 30 m, film 0.25 μm)

[0085] Injection volume; 1 μl, Split ratio 10:1

[0086] Injection temperature; 280℃

[0087] Oven temperature: Maintain at 100°C for 1 minute, increase at 10.0°C / min from 100°C to 165°C, maintain for 3 minutes after reaching 165°C, increase at 3.0°C / min from 165°C to 177°C, increase at 20.0°C / min from 177°C to 300°C, maintain for 15 minutes after reaching 300°C.

[0088] At this time, the diisocyanate compound of the present invention may include at least one selected from among 1,4-tetramethylene diisocyanate, 1,5-pentamethylene diisocyanate, 1,6-hexamethylene diisocyanate, 1,3-cyclohexylene diisocyanate, 1,4-cyclohexylene diisocyanate, isophorone diisocyanate, norbornene diisocyanate, methylenediphenyl diisocyanate, methylenedicyclohexyl isocyanate, toluene diisocyanate, m-xylylene diisocyanate, p-xylylene diisocyanate, and o-xylylene diisocyanate, and preferably may include m-xylylene diisocyanate.

[0089] Additionally, the diisocyanate compound may be included in an amount of 98.00 to 99.99 wt%, preferably 99.00 to 99.99 wt%, more preferably 99.30 to 99.99 wt%, and even more preferably 99.60 to 99.95 wt%, based on the total weight of the isocyanate composition.

[0090]

[0091] Meanwhile, when measured under the measurement conditions of the gas chromatography mass spectrometry, the compound having a retention time of 10.5 to 12.5 minutes, preferably 11.0 to 12.0 minutes, more preferably 11.4 to 11.6 minutes may be a by-product and / or compound generated in the process of manufacturing a diisocyanate compound, and is generally removed in the purification process during the synthesis of the diisocyanate compound. In the present invention, the amount of the compound having a retention time of 10.5 to 12.5 minutes, preferably 11.0 to 12.0 minutes, more preferably 11.4 to 11.6 minutes, when measured under the measurement conditions of the gas chromatography mass spectrometry, removed in the purification process can be controlled to be contained in the isocyanate composition in a specific content range, and may also be a compound additionally added to the diisocyanate compound.

[0092] In addition, when measured under the measurement conditions of the above gas chromatography mass spectrometry, a compound having a retention time of 10.5 to 12.5 minutes, preferably 11.0 to 12.0 minutes, and more preferably 11.4 to 11.6 minutes may have a mass-to-charge ratio (m / z) of 148 to 150.

[0093] In addition, when measured under the measurement conditions of the above gas chromatography mass spectrometry, a compound having a retention time of 10.5 to 12.5 minutes, preferably 11.0 to 12.0 minutes, and more preferably 11.4 to 11.6 minutes may have a mass-to-charge ratio (m / z) of 119 to 121.

[0094] In addition, when measured under the measurement conditions of the above gas chromatography mass spectrometry, a compound having a retention time of 10.5 to 12.5 minutes, preferably 11.0 to 12.0 minutes, and more preferably 11.4 to 11.6 minutes may have a mass-to-charge ratio (m / z) of 106 to 108.

[0095] In addition, when measured under the measurement conditions of the above gas chromatography mass spectrometry, a compound having a retention time of 10.5 to 12.5 minutes, preferably 11.0 to 12.0 minutes, and more preferably 11.4 to 11.6 minutes may have a mass-to-charge ratio (m / z) of 93 to 95.

[0096] In addition, when measured under the measurement conditions of the above gas chromatography mass spectrometry, a compound having a retention time of 10.5 to 12.5 minutes, preferably 11.0 to 12.0 minutes, and more preferably 11.4 to 11.6 minutes may have a mass-to-charge ratio (m / z) of 76 to 78.

[0097] In addition, when measured under the measurement conditions of the above gas chromatography mass spectrometry, a compound having a retention time of 10.5 to 12.5 minutes, preferably 11.0 to 12.0 minutes, and more preferably 11.4 to 11.6 minutes may have a mass-to-charge ratio (m / z) of 64 to 66.

[0098] Preferably, when measured under the measurement conditions of the above gas chromatography mass spectrometry, the compound having a retention time of 10.5 to 12.5 minutes, preferably 11.0 to 12.0 minutes, and more preferably 11.4 to 11.6 minutes may be a compound represented by the following chemical formula 1.

[0099] [Chemical Formula 1]

[0100]

[0101] In the above chemical formula 1, B1 is -CH2-, -CH2CH2-, -CH2CH2CH2-, -CH2CH2CH2CH2- or -CH2CH2CH2CH2CH2-, and preferably -CH2-, -CH2CH2- or -CH2CH2CH2-.

[0102] In the above chemical formula 1, R1 is -H, a straight-chain alkyl group of C1 to C12 or a branched alkyl group of C3 to C12, preferably a straight-chain alkyl group of C1 to C12, and more preferably a straight-chain alkyl group of C1 to C3.

[0103] Specifically, the compound represented by the above chemical formula 1 may be a compound represented by the following chemical formula 1-1.

[0104] [Chemical Formula 1-1]

[0105]

[0106] In the above chemical formula 1-1, B1 is -CH2-, -CH2CH2- or -CH2CH2CH2-, and R1 is a straight-chain alkyl group having C1 to C12, preferably a straight-chain alkyl group having C1 to C3.

[0107] Meanwhile, the isocyanate composition of the present invention can satisfy the following condition (1).

[0108] (1) 0.1 ppm ≤ A ≤ 60 ppm, preferably 0.2 ppm ≤ A ≤ 40 ppm, more preferably 0.4 ppm ≤ A ≤ 20 ppm, and even more preferably 0.75 ppm ≤ A ≤ 10 ppm

[0109] In the above condition (1), A represents the content (ppm) of a compound having a retention time of 10.5 to 12.5 minutes, preferably 11.0 to 12.0 minutes, and more preferably 11.4 to 11.6 minutes, when measured under the measurement conditions of the gas chromatography mass spectrometry, relative to the total weight of the isocyanate composition. If in the condition (1), A is less than 0.1 ppm, there may be a problem of increased yellowness when manufacturing an optical lens using the isocyanate composition of the present invention, and if it exceeds 60 ppm, not only may the storage stability deteriorate, but there may also be a problem of increased yellowness when manufacturing an optical lens using the isocyanate composition of the present invention.

[0110]

[0111] Furthermore, the isocyanate composition of the present invention may further include a compound represented by the following chemical formula 2.

[0112] [Chemical Formula 2]

[0113]

[0114] In the above chemical formula 2, B2 is -CH2-, -CH2CH2-, -CH2CH2CH2-, -CH2CH2CH2CH2- or -CH2CH2CH2CH2CH2-, and preferably -CH2-, -CH2CH2- or -CH2CH2CH2-.

[0115] The compound represented by the above chemical formula 2 may be a by-product and / or compound produced in the process of manufacturing a diisocyanate compound, and is generally removed in a purification process during the diisocyanate compound synthesis process. In the present invention, the amount of the compound represented by the above chemical formula 2 removed in the purification process may be controlled to be contained in an isocyanate composition within a specific content range, and may also be a compound additionally added to a diisocyanate compound.

[0116] In addition, the isocyanate composition of the present invention can satisfy the following condition (2).

[0117] (2) 0.1 ppm ≤ B ≤ 100 ppm, preferably 0.5 ppm ≤ B ≤ 50 ppm, more preferably 1.0 ppm ≤ B ≤ 30 ppm, and even more preferably 2.0 ppm ≤ B ≤ 8.0 ppm

[0118] In the above condition (2), B represents the content (ppm) of the compound represented by the above chemical formula 2 with respect to the total weight of the isocyanate composition. If in the condition (2), B is less than 0.1 ppm, there may be a problem of reduced storage stability such as yellowing and / or whitening, and if it exceeds 100 ppm, there may be a problem of deformation occurring when manufacturing an optical lens using the isocyanate composition of the present invention.

[0119] In addition, the isocyanate composition of the present invention may contain a compound represented by the above chemical formula 2 and a compound having a retention time of 10.5 to 12.5 minutes, preferably 11.0 to 12.0 minutes, and more preferably 11.4 to 11.6 minutes when measured under the measurement conditions of the gas chromatography mass spectrometry, in a weight ratio of 1:0.05 to 0.6, preferably 1:0.08 to 0.5, and more preferably 1:0.1 to 0.3. If the weight ratio is less than 1:0.05, when manufacturing an optical lens using the isocyanate composition of the present invention, not only may the yellowness increase, but there may also be a problem of deformation such as striae, and if it exceeds 1:0.6, there may be a problem of reduced storage stability such as yellowing and / or whitening, and there may also be a problem of increased yellowness when manufacturing an optical lens using the isocyanate composition of the present invention.

[0120]

[0121] Meanwhile, the isocyanate composition of the present invention can satisfy the following condition (3).

[0122] (3) 0% ≤ D - C ≤ 2.0%, preferably 0% ≤ D - C ≤ 1.5%, more preferably 0% ≤ D - C ≤ 1.0%, even more preferably 0% ≤ D - C ≤ 0.5%, even more preferably 0.001% ≤ D - C ≤ 0.1%, most preferably 0.001% ≤ D - C ≤ 0.05%

[0123] In the above condition (3), C represents the haze value of the isocyanate composition, and D represents the haze value measured after storing the isocyanate composition under conditions of a temperature of 20°C or lower, preferably a temperature of 0 to 20°C, and a humidity of 1%RH or lower, preferably a humidity of 0.0001 to 1%RH, for 160 to 200 days, preferably 170 to 190 days.

[0124]

[0125] Furthermore, the method for storing the isocyanate composition of the present invention includes a first step and a second step.

[0126] First, the first step of the method for preserving an isocyanate composition of the present invention can prepare an isocyanate composition including a diisocyanate compound and a compound having a retention time of 10.5 to 12.5 minutes, preferably 11.0 to 12.0 minutes, and more preferably 11.4 to 11.6 minutes when measured under the measurement conditions of the following gas chromatography mass spectrometry.

[0127] <Measurement conditions for gas chromatography mass spectrometry>

[0128] Column; DB-17MS (inner diameter 0.25 mm × length 30 m, film 0.25 μm)

[0129] Injection volume; 1 μl, Split ratio 10:1

[0130] Injection temperature; 280℃

[0131] Oven temperature: Maintain at 100°C for 1 minute, increase at 10.0°C / min from 100°C to 165°C, maintain for 3 minutes after reaching 165°C, increase at 3.0°C / min from 165°C to 177°C, increase at 20.0°C / min from 177°C to 300°C, maintain for 15 minutes after reaching 300°C.

[0132] In addition, the isocyanate composition prepared in the first step can satisfy the following condition (1).

[0133] (1) 0.1 ppm ≤ A ≤ 60 ppm, preferably 0.2 ppm ≤ A ≤ 40 ppm, more preferably 0.4 ppm ≤ A ≤ 20 ppm, and even more preferably 0.75 ppm ≤ A ≤ 10 ppm

[0134] In the above condition (1), A represents the content (ppm) of a compound having a retention time of 10.5 to 12.5 minutes, preferably 11.0 to 12.0 minutes, and more preferably 11.4 to 11.6 minutes, when measured under the measurement conditions of the gas chromatography mass spectrometry, relative to the total weight of the isocyanate composition.

[0135] In addition, the isocyanate composition prepared in the first step may further include a compound represented by the following chemical formula 2.

[0136] [Chemical Formula 2]

[0137]

[0138] In the above chemical formula 2, B2 is -CH2-, -CH2CH2-, -CH2CH2CH2-, -CH2CH2CH2CH2- or -CH2CH2CH2CH2CH2-, and preferably -CH2-, -CH2CH2- or -CH2CH2CH2-.

[0139] In addition, the isocyanate composition prepared in the first step can satisfy the following condition (2).

[0140] (2) 0.1 ppm ≤ B ≤ 100 ppm, preferably 0.5 ppm ≤ B ≤ 50 ppm, more preferably 1.0 ppm ≤ B ≤ 30 ppm, and even more preferably 2.0 ppm ≤ B ≤ 8.0 ppm

[0141] In the above condition (2), B represents the content (ppm) of the compound represented by the above chemical formula 2 with respect to the total weight of the isocyanate composition.

[0142]

[0143] Next, the second step of the method for storing the isocyanate composition of the present invention may be to store the isocyanate composition prepared in the first step under a nitrogen-substituted atmosphere, at a temperature of 20°C or lower, preferably 0 to 20°C, more preferably 5 to 15°C, and a humidity of 1%RH or lower, preferably 0.0001 to 1%RH, more preferably 0.001 to 0.1%RH. If the storage temperature in the second step exceeds 20°C, not only may the storage stability deteriorate, but also haze may increase, causing a problem in that the optical lens manufactured using the composition may be opaque and / or in that the optical lens may not be manufactured using the composition. If the storage humidity in the second step exceeds 1%RH, not only may the storage stability deteriorate, but also haze may increase, causing a problem in that the optical lens manufactured using the composition may be opaque.

[0144]

[0145] Meanwhile, the optical lens of the present invention may include the isocyanate composition of the present invention, and may have a yellowness (YI) of 2.5 or less, preferably 0.1 to 2.0, and more preferably 0.5 to 1.5.

[0146]

[0147] Furthermore, the non-foam resin of the present invention may include the isocyanate composition of the present invention.

[0148] The non-foam resin of the present invention is a resin that does not have a foam shape, and can be used as a coating agent, an adhesive, a sealant, or an elastomer, but is not limited thereto.

[0149] As a specific example, the non-foaming resin of the present invention may be a reaction product of the isocyanate composition of the present invention and an active hydrogen group-containing component. The active hydrogen group-containing component may include a polyol component (a component mainly containing a polyol having two or more hydroxyl groups), a polythiol component (a component mainly containing a polythiol having two or more mercapto groups (thiol groups)), a polyamine component (a compound mainly containing a polyamine having two or more amino groups), etc., and a preferred example of the active hydrogen group-containing component may be a raw material required for producing a polyurethane resin.

[0150] Meanwhile, the non-foam resin of the present invention used for coating, adhesive, sealant or elastomer may be a raw material used in the manufacture of automobiles, ships, flexible packaging, food packaging, construction, paints, inks, solar cells, microcapsules, adhesives for displays, optical materials and fuel cells, but is not limited thereto.

[0151]

[0152] Furthermore, a method for producing the isocyanate composition of the present invention described above will be described as an example as follows.

[0153] The isocyanate composition is synthesized by reacting an amine compound with phosgene in a solvent.

[0154] Solvents that can be used in the above phosgenation reaction include aromatic hydrocarbon solvents such as benzene, toluene, xylene, and ethylbenzene; chlorinated aromatic hydrocarbon solvents such as monochlorobenzene, 1,2-dichlorobenzene, and 1,4-dichlorobenzene; and chlorinated hydrocarbon solvents such as dichloromethane, chloroform, and carbon tetrachloride. Two or more of these can be used in combination.

[0155] The amine compound used in the above phosgenation reaction may be, for example, an amine compound obtained by hydrogenating a nitro compound or a chloride thereof. Specifically, the amine compound may be at least one selected from the group consisting of 1,4-tetramethylene diamine, 1,5-pentamethylene diamine, 1,6-hexamethylene diamine, 1,3-cyclohexylene diamine, 1,4-cyclohexylene diamine, isophorone diamine, diamine, methylenediphenyl diamine, methylenedicyclohexyl diamine, toluene diamine, m-xylylene diamine, p-xylylene diamine, and o-xylylene diamine, and salts thereof, and preferably m-xylylene diamine, p-xylylene diamine, o-xylylene diamine, or a salt thereof.

[0156] The above amine compound may be included in an amount of 1 to 20 parts by weight per 100 parts by weight of the solvent. If the content of the amine compound exceeds 20 parts by weight, there is a risk of precipitation of a large amount of the amine compound. Preferably, the content may be included in an amount of 1 to 15 parts by weight or 3 to 10 parts by weight.

[0157] Specifically, the phosgenation reaction can be carried out by a direct phosgenation method (Method 1) in which an amine compound is directly reacted with phosgene; a method in which an amine compound is reacted with anhydrous hydrochloric acid to form an amine-hydrochloride compound and then the formed salt is reacted with phosgene (Method 2); or a method in which an amine compound is reacted with carbonic acid to form an aliphatic amine-carbonate compound and then the formed salt is reacted with phosgene (Method 3).

[0158] The direct phosgenation method of the above method 1 can be performed by reacting an amine compound and phosgene in the above organic solvent. At this time, the phosgene can be introduced all at once at the beginning of the reaction, or can be introduced in part at the beginning of the reaction and the remainder can be introduced in installments during the reaction.

[0159] Meanwhile, the above method 1 can be performed by a first step of dissolving a portion of phosgene in the solvent and then adding the amine compound; and a second step of adding the remaining phosgene after the addition of the amine compound is complete and causing a reaction. At this time, the first step is preferably performed at a temperature of -15°C to -10°C to prevent leakage of highly toxic phosgene and also to prevent rapid heat generation when the amine compound is added, and the phosgenation reaction in the second step can be controlled at a temperature of 120°C to 140°C so that the reaction can occur at an appropriate reaction rate without concern for decomposition of the amine compound.

[0160] In the case of the above method 2, it can be carried out by a step of reacting an amine compound with hydrochloric acid in an organic solvent to form an amine-hydrochloride compound, and then introducing phosgene to cause the reaction. The formation of the amine-hydrochloride compound can be carried out at a temperature of 30°C or lower, preferably at a temperature of about 23±5°C, and the reaction after the introduction of phosgene can be controlled to 120°C to 140°C. When carried out under such temperature conditions, the solubility of the amine-hydrochloride compound can be increased, and thermal decomposition of the isocyanate can be prevented, thereby producing a high-purity isocyanate compound in high yield.

[0161] In the case of the above method 3, it can be carried out by a step of reacting an amine compound with carbonic acid in a solvent to form an amine-carbonate compound, and then introducing phosgene to cause the reaction. At this time, the formation of the amine-carbonate compound can be carried out at a temperature of 30°C or lower, preferably about 23±5°C, and the reaction after the introduction of phosgene can be controlled to 80°C to 180°C. Preferably, it can be in the range of 100°C or higher, or 120°C or higher, and 150°C or lower, or 140°C or lower. When carried out under such temperature conditions, the solubility of the amine-carbonate compound is increased, and thermal decomposition of the isocyanate is prevented, thereby producing a high-purity isocyanate compound in a high yield.

[0162] After the reaction with phosgene is completed according to each method, a removal process such as nitrogen bubbling for unreacted phosgene and hydrogen chloride gas and a solvent removal process such as distillation may be optionally further performed, and these processes may be performed according to a conventional method.

[0163]

[0164] Hereinafter, the present invention will be described in more detail through examples, but the following examples do not limit the scope of the present invention, and should be interpreted as helping to understand the present invention.

[0165]

[0166] Preparation Example 1: Preparation of a compound

[0167] (1) A compound with a retention time of 11.5 minutes was prepared when measured using a gas chromatograph mass spectrometer (GC-MSD) under the following measurement conditions.

[0168] <Measurement conditions for gas chromatography mass spectrometry>

[0169] Measuring instrument; Agilent 8890 5977C GC-MS

[0170] Column; DB-17MS (inner diameter 0.25 mm × length 30 m, film 0.25 μm)

[0171] Filtration filter; 0.45 ㎛ Teflon filter

[0172] Injection concentration; 1.0 wt%, dichloromethane solution

[0173] Injection volume; 1 μl, Split ratio 10:1

[0174] Injection temperature; 280℃

[0175] Carrier gas; He, 1 mL / min

[0176] Detection method; Scan method (30 to 550 m / z)

[0177] Oven temperature: Maintain at 100°C for 1 minute, increase at 10.0°C / min from 100°C to 165°C, maintain for 3 minutes after reaching 165°C, increase at 3.0°C / min from 165°C to 177°C, increase at 20.0°C / min from 177°C to 300°C, maintain for 15 minutes after reaching 300°C.

[0178] (2) It was confirmed that the compound with a prepared retention time of 11.5 minutes was a compound represented by the following chemical formula 1-2 with mass-to-charge ratios (m / z) of 149, 120, 107, 94, 77, and 65.

[0179] [Chemical Formula 1-2]

[0180]

[0181] In the above chemical formula 1-2, B1 is -CH2- and R1 is a methyl group.

[0182]

[0183] Example 1: Preparation of isocyanate composition

[0184] (1) 471 g of 1,2-dichlorobenzene and 32.5 g of m-xylylene diamine (m-XDA) with a purity of 99.4% were introduced into the reactor, and stirred while injecting anhydrous hydrochloric acid at a rate of 20 g / hr at room temperature (23±5°C). During the process of injecting the anhydrous hydrochloric acid, the internal temperature of the reactor rose to 50°C.

[0185] (2) After the above anhydrous hydrochloric acid was injected for 4 hours, the reactor was cooled until the internal temperature became room temperature (23±5℃). Thereafter, 43 ml of liquid phosgene was injected into the reactor, and the reactor was heated until the internal temperature reached 130℃. At this time, a dry ice-acetone cooler was used to prevent phosgene from leaking to the outside from the time of phosgene injection until the time of confirming the completion of the reaction, which will be described later. After the internal temperature of the reactor reached 130℃, the internal temperature of the reactor was maintained at 125 to 135℃ for 2 hours so that the solution contained inside the reactor became transparent. By confirming the completion of the reaction when the solution contained inside the reactor became transparent, it was confirmed that a reactant from which phosgene was removed was produced inside the reactor.

[0186] (3) Afterwards, nitrogen was blown into the reactor and the reactor was cooled until the internal temperature reached 80°C, and the reactant generated inside the reactor was obtained.

[0187] (4) The solvent contained in the reactant obtained through vacuum distillation was removed, and a purification process was performed by distillation using a thin film distillation device (TFE), and then an additional vacuum purification process was performed to remove the oligomer contained in the reactant, thereby finally manufacturing an isocyanate composition. Purification using a thin film distillation device (TFE) was performed under the conditions of a feeding temperature of 150°C, a thin film distillation device (TFE) temperature of 160°C, a vacuum of 0.5 torr, and a feeding rate of 20 ml / min, and vacuum purification was performed under the conditions of a pressure of 3.2 mbar and a temperature of 160°C.

[0188] Meanwhile, it was confirmed that the manufactured isocyanate composition contained 0.86 ppm of the compound prepared in Preparation Example 1 based on the total weight of the manufactured isocyanate composition, and that the compound represented by the following Chemical Formula 2-2 contained 3.60 ppm based on the total weight of the manufactured isocyanate composition.

[0189] [Chemical Formula 2-2]

[0190]

[0191] In the above chemical formula 2-2, B2 is -CH2-.

[0192]

[0193] Example 2: Preparation of isocyanate composition

[0194] An isocyanate composition was prepared in the same manner as in Example 1. However, unlike Example 1, purification using a thin film distillation device (TFE) was performed under the following conditions: feeding temperature of 150°C, TFE temperature of 160°C, vacuum of 0.8 torr, and feeding rate of 20 ml / min, and reduced pressure purification was performed under the following conditions: pressure of 3.2 mbar, temperature of 160°C.

[0195] Meanwhile, it was confirmed that the manufactured isocyanate composition contained 25.49 ppm of the compound prepared in Preparation Example 1 based on the total weight of the manufactured isocyanate composition, and that the compound represented by Chemical Formula 2-2 contained 46.10 ppm based on the total weight of the manufactured isocyanate composition.

[0196]

[0197] Example 3: Preparation of isocyanate composition

[0198] An isocyanate composition was prepared in the same manner as in Example 1. However, unlike Example 1, purification using a thin film distillation device (TFE) was performed under the following conditions: feeding temperature of 150°C, TFE temperature of 160°C, vacuum of 1.0 torr, and feeding rate of 20 ml / min, and reduced pressure purification was performed under the following conditions: pressure of 3.2 mbar, temperature of 160°C.

[0199] Meanwhile, it was confirmed that the manufactured isocyanate composition contained 0.73 ppm of the compound prepared in Preparation Example 1 based on the total weight of the manufactured isocyanate composition, and that the compound represented by Chemical Formula 2-2 contained 10.80 ppm based on the total weight of the manufactured isocyanate composition.

[0200]

[0201] Example 4: Preparation of isocyanate composition

[0202] (1) 471 g of 1,2-dichlorobenzene and 32.5 g of m-xylylene diamine (m-XDA) with a purity of 99.4% were introduced into the reactor, and stirred while injecting anhydrous hydrochloric acid at a rate of 20 g / hr at room temperature (23±5°C). During the process of injecting the anhydrous hydrochloric acid, the internal temperature of the reactor rose to 50°C.

[0203] (2) After the above anhydrous hydrochloric acid was injected for 4 hours, the reactor was cooled until the internal temperature became room temperature (23±5℃). Thereafter, 43 ml of liquid phosgene was injected into the reactor, and the reactor was heated until the internal temperature reached 130℃. At this time, a dry ice-acetone cooler was used to prevent phosgene from leaking to the outside from the time of phosgene injection until the time of confirming the completion of the reaction, which will be described later. After the internal temperature of the reactor reached 130℃, the internal temperature of the reactor was maintained at 125 to 135℃ for 2 hours so that the solution contained inside the reactor became transparent. By confirming the completion of the reaction when the solution contained inside the reactor became transparent, it was confirmed that a reactant from which phosgene was removed was produced inside the reactor.

[0204] (3) Afterwards, nitrogen was blown into the reactor and the reactor was cooled until the internal temperature reached 80°C, and the reactant generated inside the reactor was obtained.

[0205] (4) The solvent contained in the reactant obtained through vacuum distillation was removed, and a purification process was performed by distillation using a thin film distillation device (TFE) to remove the oligomer contained in the reactant, thereby finally producing an isocyanate composition. The purification using the thin film distillation device (TFE) was performed under the following conditions: a feeding temperature of 80°C, a thin film distillation device (TFE) temperature of 150°C, a vacuum of 0.5 torr, and a feeding rate of 30 ml / min.

[0206] Meanwhile, it was confirmed that the manufactured isocyanate composition contained 39.90 ppm of the compound prepared in Preparation Example 1 based on the total weight of the manufactured isocyanate composition, and that the compound represented by Chemical Formula 2-2 contained 178.10 ppm based on the total weight of the manufactured isocyanate composition.

[0207]

[0208] Comparative Example 1: Preparation of isocyanate composition

[0209] An isocyanate composition was prepared in the same manner as in Example 4. However, unlike Example 4, purification using a thin film distillation device (TFE) was performed under the following conditions: feeding temperature of 150°C, thin film distillation device (TFE) temperature of 160°C, vacuum of 0.01 torr, and feeding rate of 2.6 ml / min.

[0210] Meanwhile, it was confirmed that the manufactured isocyanate composition contained the compound represented by the above chemical formula 2-2 at 1.90 ppm based on the total weight of the manufactured isocyanate composition.

[0211]

[0212] Experimental Example 1: APHA Color and Haze Measurement

[0213] According to the method of ASTM E313, the APHA color and haze of each of the isocyanate compositions manufactured in Examples 1 to 4 and Comparative Example 1 were measured using Ultrascan Pro from HunterLab (light source: C / 2) and are shown in Table 1 below.

[0214]

[0215] As can be seen in Table 1, it was confirmed that the isocyanate compositions prepared in Example 3 and Comparative Example 1 had significantly high APHA color values ​​that made them unusable as transparent optical materials.

[0216]

[0217] Except for the isocyanate compositions manufactured in Example 3 and Comparative Example 1, each of the isocyanate compositions manufactured in Examples 1 to 2 and 4 was stored for 180 days under nitrogen-substituted atmosphere, temperature of 15°C and humidity of 0.1%RH, and then the APHA color and haze of each of the stored isocyanate compositions manufactured in Examples 1 to 2 and 4 were measured (light source: C / 2) and are shown in Table 2 below.

[0218]

[0219] As can be seen in Table 2, it was confirmed that the isocyanate compositions manufactured in Examples 1 and 2 had low haze values ​​and low APHA color values ​​even after 180 days of storage.

[0220] However, it was confirmed that the isocyanate composition manufactured in Example 4 had a high haze value after 180 days of storage.

[0221]

[0222] Manufacturing Examples 1 to 2, 4: Manufacturing of optical lenses

[0223] Each of the isocyanate compositions manufactured in Examples 1 to 2 and 4 was stirred and mixed at room temperature (= 23°C) for 20 minutes with 0.04 g of ZELEC™ UN (manufactured by Stepan) as an internal release agent and 0.04 g of Biosorb™ 583 (manufactured by Sakai Chemical industry Co., Ltd) as an ultraviolet absorbent, and then a mixture was prepared. 0.24 g of a dye solution containing 0.047 wt% of Quinizarin Blue and 0.002 g of DBTC (dibutyltin dichloride) were added to the mixture and stirred for 10 minutes. 19.2 g of 2,3-bis(2-sulfanyl ethyl sulfanyl)propane-1-thiol was added, and then the mixture was stirred for 1 hour while degassing under a pressure condition of 5 mbar, thereby preparing a composition for polyisocyanate polymerization.

[0224] The prepared polyisocyanate polymerization composition was filtered using a 1 μm PTFE filter and then injected into a mold formed of a glass mold and tape, respectively. Thereafter, the mold was placed in an oven and polymerization was performed for 20 hours while gradually increasing the temperature from 10°C to 120°C. After completion of the polymerization, the mold was taken out from the oven and released to obtain each plastic optical lens. The obtained optical lenses were annealed at 120°C for 6 hours to manufacture optical lenses having a thickness of 3 mm, respectively. The optical lens manufactured using the isocyanate composition manufactured in Example 1 is shown as Manufacturing Example 1 in Table 3 below, the optical lens manufactured using the isocyanate composition manufactured in Example 2 is shown as Manufacturing Example 2 in Table 3 below, and the optical lens manufactured using the isocyanate composition manufactured in Example 4 is shown as Manufacturing Example 4 in Table 3 below.

[0225]

[0226] Experimental Example 2: Color Difference Measurement

[0227] According to the method of ASTM D1209, the yellowness (YI) of each optical lens manufactured in Manufacturing Examples 1 to 2 and 4 was measured using Ultrascan Pro from HunterLab, and the results are shown in Table 3.

[0228]

[0229] As can be seen in Table 3, the optical lens of Manufacturing Example 1 was found to have particularly low yellowness.

[0230]

[0231] The above illustrates and describes specific embodiments. However, the invention is not limited to the aforementioned embodiments, and those skilled in the art will readily appreciate that various modifications and implementations can be made without departing from the spirit and scope of the invention as set forth in the claims below.

Claims

1. Diisocyanate compounds; and A compound having a retention time of 10.5 to 12.5 minutes when measured under the measurement conditions of the following gas chromatography mass spectrometry; An isocyanate composition comprising: <Measurement conditions for gas chromatography mass spectrometry> Column; DB-17MS (inner diameter 0.25 mm × length 30 m, film 0.25 μm) Injection volume; 1 μl, Split ratio 10:1 Injection temperature; 280℃ Oven temperature: Maintain at 100°C for 1 minute, increase at 10.0°C / min from 100°C to 165°C, maintain for 3 minutes after reaching 165°C, increase at 3.0°C / min from 165°C to 177°C, increase at 20.0°C / min from 177°C to 300°C, maintain for 15 minutes after reaching 300°C.

2. In paragraph 1, An isocyanate composition wherein the compounds having a retention time of 10.5 to 12.5 minutes have mass-to-charge ratios (m / z) of 148 to 150, 119 to 121, 106 to 108, 93 to 95, 76 to 78, and 64 to 66.

3. In paragraph 2, An isocyanate composition wherein the compound having a retention time of 10.5 to 12.5 minutes is a compound represented by the following chemical formula 1. [Chemical Formula 1] In the above chemical formula 1, B1 is -CH2-, -CH2CH2-, -CH2CH2CH2-, -CH2CH2CH2CH2-, or -CH2CH2CH2CH2CH2-, and R1 is -H, a straight-chain alkyl group of C1 to C12, or a branched alkyl group of C3 to C12.

4. In paragraph 1, The above isocyanate composition is an isocyanate composition that satisfies the following condition (1). (1) 0.1 ppm ≤ A ≤ 60 ppm In the above condition (1), A represents the content (ppm) of the compound having a retention time of 10.5 to 12.5 minutes with respect to the total weight of the isocyanate composition.

5. In paragraph 1, An isocyanate composition further comprising a compound represented by the following chemical formula 2. [Chemical Formula 2] In the above chemical formula 2, B2 is -CH2-, -CH2CH2-, -CH2CH2CH2-, -CH2CH2CH2CH2-, or -CH2CH2CH2CH2CH2-.

6. In paragraph 5, The above isocyanate composition is an isocyanate composition that satisfies the following condition (2). (2) 0.1 ppm ≤ B ≤ 100 ppm In the above condition (2), B represents the content (ppm) of the compound represented by the above chemical formula 2 with respect to the total weight of the isocyanate composition.

7. In paragraph 5, The above isocyanate composition comprises a compound represented by chemical formula 2 and a compound having a retention time of 10.5 to 12.5 minutes in a weight ratio of 1:0.05 to 0.

6.

8. In paragraph 1, An isocyanate composition comprising at least one selected from the group consisting of 1,4-tetramethylene diisocyanate, 1,5-pentamethylene diisocyanate, 1,6-hexamethylene diisocyanate, 1,3-cyclohexylene diisocyanate, 1,4-cyclohexylene diisocyanate, isophorone diisocyanate, norbornene diisocyanate, methylenediphenyl diisocyanate, methylenedicyclohexyl isocyanate, toluene diisocyanate, m-xylylene diisocyanate, p-xylylene diisocyanate, and o-xylylene diisocyanate.

9. In paragraph 1, An isocyanate composition wherein the above diisocyanate compound is m-xylylene diisocyanate.

10. In paragraph 3, An isocyanate composition, wherein the compound represented by the above chemical formula 1 is a compound represented by the following chemical formula 1-1. [Chemical Formula 1-1] In the above chemical formula 1-1, B1 is -CH2-, -CH2CH2- or -CH2CH2CH2-, and R1 is a straight-chain alkyl group of C1 to C12.

11. In paragraph 5, An isocyanate composition wherein the compound represented by the above chemical formula 2 is a compound represented by the following chemical formula 2-1. [Chemical Formula 2-1] In the above chemical formula 2-1, B2 is -CH2-, -CH2CH2- or -CH2CH2CH2-.

12. In paragraph 1, The above isocyanate composition is an isocyanate composition that satisfies the following condition (3). (3) 0% ≤ D - C ≤ 2.0% In the above condition (3), C represents the haze value of the isocyanate composition, and D represents the haze value measured after storing the isocyanate composition under conditions of a temperature of 20°C or lower and a humidity of 1%RH or lower for 160 to 200 days.

13. A first step of preparing an isocyanate composition comprising a diisocyanate compound and a compound having a retention time of 10.5 to 12.5 minutes when measured under the measurement conditions of the following gas chromatography mass spectrometry; and A second step of storing the above isocyanate composition under a nitrogen-substituted atmosphere, at a temperature of 20°C or lower and a humidity of 1%RH or lower; A method for storing an isocyanate composition, comprising: <Measurement conditions for gas chromatography mass spectrometry> Column; DB-17MS (inner diameter 0.25 mm × length 30 m, film 0.25 μm) Injection volume; 1 μl, Split ratio 10:1 Injection temperature; 280℃ Oven temperature: Maintain at 100°C for 1 minute, increase at 10.0°C / min from 100°C to 165°C, maintain for 3 minutes after reaching 165°C, increase at 3.0°C / min from 165°C to 177°C, increase at 20.0°C / min from 177°C to 300°C, maintain for 15 minutes after reaching 300°C.

14. In paragraph 13, A method for storing an isocyanate composition, wherein the compound having a retention time of 10.5 to 12.5 minutes is a compound represented by the following chemical formula 1. [Chemical Formula 1] In the above chemical formula 1, B1 is -CH2-, -CH2CH2-, -CH2CH2CH2-, -CH2CH2CH2CH2-, or -CH2CH2CH2CH2CH2-, and R1 is -H, a straight-chain alkyl group of C1 to C12, or a branched alkyl group of C3 to C12.

15. In paragraph 13, A method for storing an isocyanate composition, wherein the isocyanate composition prepared in the above first step satisfies the following condition (1). (1) 0.1 ppm ≤ A ≤ 60 ppm In the above condition (1), A represents the content (ppm) of the compound having a retention time of 10.5 to 12.5 minutes with respect to the total weight of the isocyanate composition.

16. In paragraph 13, A method for storing an isocyanate composition, wherein the isocyanate composition further comprises a compound represented by the following chemical formula 2. [Chemical Formula 2] In the above chemical formula 2, B2 is -CH2-, -CH2CH2-, -CH2CH2CH2-, -CH2CH2CH2CH2-, or -CH2CH2CH2CH2CH2-.

17. In paragraph 16, A method for storing an isocyanate composition, wherein the isocyanate composition prepared in the above first step satisfies the following condition (2). (2) 0.1 ppm ≤ B ≤ 100 ppm In the above condition (2), B represents the content (ppm) of the compound represented by the above chemical formula 2 with respect to the total weight of the isocyanate composition.

18. In paragraph 13, The second step is a method for storing an isocyanate composition, wherein the isocyanate composition is stored under a nitrogen-substituted atmosphere, at a temperature of 0 to 20°C and a humidity of 0.0001 to 1%RH.

19. An optical lens comprising the isocyanate composition of paragraph 1.

20. In paragraph 19, The above optical lens is an optical lens having a yellowness (YI) of 2.5 or less.

21. A non-foam resin comprising the isocyanate composition of claim 1.

22. In paragraph 21, The above non-foam resin is a non-foam resin for coating, adhesive, sealant or elastomer.

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