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 an isocyanate composition using the same

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

[0002]

[0003] Isocyanate compounds serve as raw materials for polyurethanes and are widely used in coatings, adhesives, paints, foams, and optical materials. For polyurethanes used in fields requiring excellent appearance properties, particularly in optical applications where transparency is required, minimal discoloration is necessary. To achieve this, it is crucial not only that the polyurethane reaction does not cause discoloration, but also that the isocyanate compounds themselves—specifically, polyvalent isocyanate compounds with difunctionality or higher—do not undergo discoloration.

[0004] However, because isocyanate compounds are highly reactive, they are prone to oxidation by oxygen in the air or deterioration and discoloration due to the formation of self-polymers during storage, and there have been problems with discoloration or cloudiness occurring in optical products such as urethane lenses to which they are applied.

[0005] In response to this, various methods have been researched and proposed to inhibit discoloration in isocyanate compounds and products manufactured using them, such as sealing with nitrogen gas to block air and refrigerating, or storing with additives like UV absorbers.

[0006] However, when isocyanate compounds are moved from their storage location to the atmosphere for use, the isocyanate compounds may become discolored or cloudy depending on the moisture content or temperature changes in the atmosphere during this process. If optical lenses or the like are manufactured using isocyanate compounds that have become discolored or cloudy, there is a problem of reduced clarity and degraded quality.

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

[0008]

[0009] The present invention has been devised to overcome the aforementioned problems and aims to provide an isocyanate composition having excellent storage stability even when a diisocyanate compound is stored for a long time by including specific conditions and specific compounds, an optical lens containing the same, and a method for storing an isocyanate composition using the same.

[0010] In addition, the present invention aims to provide an isocyanate composition with improved clarity, an optical lens containing 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 with excellent thermal stability using the isocyanate composition, an optical lens containing 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 producing a transparent optical material (e.g., an optical lens) that not only has a low likelihood of causing defects but also improves color and opacity, an optical lens containing the same, and a method for storing the isocyanate composition using the same.

[0013]

[0014] To solve the above-mentioned problem, the isocyanate composition of the present invention may include a diisocyanate compound, a dimer, and a trimer.

[0015] As a preferred embodiment of the present invention, the isocyanate composition of the present invention may satisfy the following condition (1).

[0016] (1) 0.2 wt% ≤ A ≤ 2.0 wt%

[0017] In the above condition (1), A represents the content (weight%) of the dimer relative to the total weight of the isocyanate composition.

[0018] As a preferred embodiment of the present invention, the isocyanate composition of the present invention may further satisfy the following condition (2).

[0019] (2) 0.005 wt% ≤ B ≤ 0.3 wt%

[0020] In the above condition (2), B represents the content (weight%) of the trimer relative to the total weight of the isocyanate composition.

[0021] 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 1.

[0022] [Chemical Formula 1]

[0023]

[0024] In the above chemical formula 1, B1 is -CH2-, -CH2CH2-, -CH2CH2CH2-, -CH2CH2CH2CH2- or -CH2CH2CH2CH2CH2-.

[0025] As a preferred embodiment of the present invention, the compound represented by Formula 1 may be included in an amount of 200 ppm or less with respect to the total weight of the isocyanate composition.

[0026] As a preferred embodiment of the present invention, the isocyanate composition of the present invention may satisfy the following condition (3).

[0027] (3) 0.1 ppm ≤ E ≤ 100 ppm

[0028] In the above condition (3), E represents the content (ppm) of the compound represented by the above formula 1 with respect to the total weight of the isocyanate composition.

[0029] As a preferred embodiment of the present invention, the diisocyanate compound may include one or more 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, methylene diphenyl diisocyanate, methylene dicyclohexyl diisocyanate, toluene diisocyanate, m-xylylene diisocyanate, p-xylylene diisocyanate, and o-xylylene diisocyanate.

[0030] As a preferred embodiment of the present invention, the diisocyanate compound may be m-xylylene diisocyanate.

[0031] As a preferred embodiment of the present invention, the compound represented by Chemical Formula 1 may be a compound represented by Chemical Formula 1-1 below.

[0032] [Chemical Formula 1-1]

[0033]

[0034] In the above chemical formula 1-1, B1 is -CH2-, -CH2CH2- or -CH2CH2CH2-.

[0035] As a preferred embodiment of the present invention, the isocyanate composition of the present invention may satisfy the following condition (4).

[0036] (4) 0.001% ≤ D - C ≤ 0.2%

[0037] In the above conditions (4), C represents the haze value of the isocyanate composition, and D represents the haze value measured after storing the isocyanate composition for 70 to 110 days at a temperature of 20°C or lower and a humidity of 1%RH or lower.

[0038] Meanwhile, the storage method for an isocyanate composition according to the present invention may include a first step of preparing an isocyanate composition comprising a diisocyanate compound, a dimer, and a trimer, and a second step of storing the prepared isocyanate composition under a nitrogen-substituted atmosphere, at a temperature of 20°C or lower and a humidity of 1%RH or lower.

[0039] As a preferred embodiment of the present invention, the isocyanate composition may satisfy the following condition (1).

[0040] (1) 0.2 wt% ≤ A ≤ 2.0 wt%

[0041] In the above condition (1), A represents the content (weight%) of the dimer relative to the total weight of the isocyanate composition.

[0042] As a preferred embodiment of the present invention, the isocyanate composition prepared in the first step may further satisfy the following condition (2).

[0043] (2) 0.005 wt% ≤ B ≤ 0.3 wt%

[0044] In the above condition (2), B represents the content (weight%) of the trimer relative to the total weight of the isocyanate composition.

[0045] 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 1.

[0046] [Chemical Formula 1]

[0047]

[0048] In the above chemical formula 1, B1 is -CH2-, -CH2CH2-, -CH2CH2CH2-, -CH2CH2CH2CH2- or -CH2CH2CH2CH2CH2-.

[0049] As a preferred embodiment of the present invention, the compound represented by Formula 1 may be included in an amount of 200 ppm or less with respect to the total weight of the isocyanate composition prepared in the first step.

[0050] As a preferred embodiment of the present invention, the second step may store the isocyanate composition under a nitrogen-substituted atmosphere, at a temperature of 0 to 20°C and a humidity of 0.0001 to 1%RH.

[0051] Furthermore, the optical lens of the present invention may include the isocyanate composition of the present invention.

[0052] Meanwhile, the non-foam resin of the present invention may include the isocyanate composition of the present invention.

[0053] As a preferred embodiment of the present invention, the non-foam resin of the present invention may be for use as a coating agent, an adhesive, a sealant, or an elastomer.

[0054]

[0055] The isocyanate composition of the present invention, the optical lens containing the same, and the method for storing the isocyanate composition using the same not only have excellent storage stability, but also improve the clarity of the isocyanate and can improve the opacity (transparency) and color of the optical lens.

[0056]

[0057] The present invention will be described in more detail below.

[0058] Various methods have been researched and proposed to suppress discoloration in existing isocyanate compounds and products manufactured using them, such as sealing with nitrogen gas to block air and refrigerating, or adding additives like UV absorbers for storage. However, when isocyanate compounds are moved from their storage location to an atmospheric environment for use, discoloration or cloudiness may occur depending on the moisture content or temperature changes in the air during this process. Furthermore, if discolored or cloudy isocyanate compounds are used to manufacture optical lenses, there is a problem of reduced quality due to decreased clarity. Additionally, it is difficult to ensure the long-term storage stability of isocyanate compounds.

[0059] Accordingly, by including a specific compound, the present invention not only provides excellent storage stability but also improves the clarity of the isocyanate and can improve the opacity (transparency) and color of the optical lens.

[0060]

[0061] The isocyanate composition of the present invention may include a diisocyanate compound, a dimer, and a trimer.

[0062] At this time, the diisocyanate compound of the present invention may include one or more 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, methylene diphenyl diisocyanate, methylene dicyclohexyl diisocyanate, toluene diisocyanate, m-xylylene diisocyanate, p-xylylene diisocyanate, and o-xylylene diisocyanate, and preferably may include m-xylylene diisocyanate.

[0063] In addition, the diisocyanate compound may be included in an amount of 98.00 to 99.99 weight%, preferably 99.00 to 99.99 weight%, more preferably 99.30 to 99.99 weight%, and even more preferably 99.60 to 99.95 weight% based on the total weight of the isocyanate composition.

[0064]

[0065] Meanwhile, a dimer is a substance formed by the polymerization of two molecules, meaning that the two molecules are bonded by forces such as hydrogen bonding. It is also referred to as a dimer. The dimer of the present invention may be a byproduct and / or compound generated during the process of manufacturing a diisocyanate compound, and is generally removed during the purification process in the synthesis of the diisocyanate compound. The present invention may contain the dimer within a specific content range in the isocyanate composition by controlling the amount of dimer removed during the purification process, and may also be a compound additionally added to the diisocyanate compound.

[0066] In addition, a trimer is a product formed by the bonding of three molecules of low molecular weight compounds that are easy to polymerize, and refers to a compound having a molecular weight three times that of the original. The trimer of the present invention may be a byproduct and / or compound generated in the process of manufacturing a diisocyanate compound, and is generally removed during the purification process in the synthesis of the diisocyanate compound. The present invention may contain the trimer within a specific content range in the isocyanate composition by controlling the amount of trimer removed during the purification process, and may also be a compound additionally added to the diisocyanate compound.

[0067]

[0068] In addition, the isocyanate composition of the present invention can satisfy the following condition (1).

[0069] (1) 0.2 wt% ≤ A ≤ 2.0 wt%, preferably 0.4 wt% ≤ A ≤ 1.8 wt%, more preferably 0.6 wt% ≤ A ≤ 1.6 wt%, even more preferably 0.8 wt% ≤ A ≤ 1.4 wt%, and even more preferably 1.1 wt% ≤ A ≤ 1.3 wt%

[0070] In the above condition (1), A represents the content (weight%) of the dimer relative to the total weight of the isocyanate composition. If, in the above condition (1), A is less than 0.2 weight%, there may be a problem of reduced stability and reduced clarity, and if A is more than 2.0 weight%, there may be a problem of increased cloudiness when manufacturing optical lenses.

[0071] In addition, the isocyanate composition of the present invention may further satisfy the following condition (2).

[0072] (2) 0.005 wt% ≤ B ≤ 0.3 wt%, preferably 0.01 wt% ≤ B ≤ 0.25 wt%, more preferably 0.015 wt% ≤ B ≤ 0.2 wt%, even more preferably 0.02 wt% ≤ B ≤ 0.15 wt%, even more preferably 0.03 wt% ≤ B ≤ 0.1 wt%, most preferably 0.035 wt% ≤ B ≤ 0.07 wt%

[0073] In the above condition (2), B represents the content (weight%) of the trimer relative to the total weight of the isocyanate composition, and if B is less than 0.005 weight%, there may be a problem of deformation occurring during the manufacture of optical lenses, and if B is more than 0.3 weight%, there may be a problem of reduced stability and reduced clarity.

[0074]

[0075] Furthermore, the isocyanate composition of the present invention may further include a compound represented by the following chemical formula 1.

[0076] [Chemical Formula 1]

[0077]

[0078] In the above chemical formula 1, B1 is -CH2-, -CH2CH2-, -CH2CH2CH2-, -CH2CH2CH2CH2- or -CH2CH2CH2CH2CH2-, preferably -CH2-, -CH2CH2- or -CH2CH2CH2-.

[0079] The compound represented by the above chemical formula 1 may be a byproduct and / or compound generated in the process of manufacturing a diisocyanate compound, and is generally removed during the purification process in the synthesis of the diisocyanate compound. The present invention may contain the phenyl compound in a specific content range within the isocyanate composition by controlling the amount of phenyl compound removed during the purification process, and may also be a compound additionally added to the diisocyanate compound.

[0080] Specifically, the compound represented by the above chemical formula 1 may be a compound represented by the following chemical formula 1-1.

[0081] [Chemical Formula 1-1]

[0082]

[0083] In the above chemical formula 1-1, B1 is -CH2-, -CH2CH2- or -CH2CH2CH2-.

[0084] In addition, the compound represented by Formula 1 of the present invention may be 200 ppm or less with respect to the total weight of the isocyanate composition. If the compound represented by Formula 1 is included in an amount exceeding 200 ppm, there may be a problem in which mac and haze phenomena are observed during the manufacture of optical lenses.

[0085] In addition, the isocyanate composition of the present invention can satisfy the following condition (3).

[0086] (3) 0.1 ppm ≤ E ≤ 100 ppm, preferably 0.5 ppm ≤ E ≤ 50 ppm, more preferably 1.0 ppm ≤ E ≤ 30 ppm, even more preferably 1.5 ppm ≤ E ≤ 20 ppm

[0087] In the above condition (3), E represents the content (ppm) of the compound represented by the above chemical formula 1 relative to the total weight of the isocyanate composition. In the above condition (1), if E is less than 0.1 ppm, there may be a problem with reduced storage stability due to yellowing and / or cloudiness, and if it exceeds 100 ppm, there may be a problem with magma, yellowing and / or cloudiness when manufacturing an optical lens using it.

[0088] Meanwhile, the isocyanate composition of the present invention can satisfy the following condition (4).

[0089] (4) 0.001% ≤ D - C ≤ 0.2%, preferably 0.001% ≤ D - C ≤ 0.1%, more preferably 0.001% ≤ D - C ≤ 0.08%

[0090] In the above conditions (4), C represents the haze value of the isocyanate composition, and D represents the haze value measured after storing the isocyanate composition for 70 to 110 days at a temperature of 20°C or lower, preferably 0 to 20°C, and a humidity of 1%RH or lower, preferably 0.0001 to 1%RH.

[0091]

[0092] Furthermore, the storage method of the isocyanate composition of the present invention includes a first step and a second step.

[0093] First, the first step of the storage method for an isocyanate composition of the present invention may be to prepare an isocyanate composition comprising a diisocyanate compound, a dimer, and a trimer.

[0094] At this time, the diisocyanate compound, dimer, and trimer are each as described above. That is, the isocyanate composition prepared in the first step can satisfy the following condition (1).

[0095] (1) 0.2 wt% ≤ A ≤ 2.0 wt%, preferably 0.4 wt% ≤ A ≤ 1.8 wt%, more preferably 0.6 wt% ≤ A ≤ 1.6 wt%, even more preferably 0.8 wt% ≤ A ≤ 1.4 wt%, and even more preferably 1.1 wt% ≤ A ≤ 1.3 wt%

[0096] In the above condition (1), A represents the content (weight%) of the dimer relative to the total weight of the isocyanate composition.

[0097] In addition, the isocyanate composition prepared in the first step can further satisfy the following condition (2).

[0098] (2) 0.005 wt% ≤ B ≤ 0.3 wt%, preferably 0.01 wt% ≤ B ≤ 0.25 wt%, more preferably 0.015 wt% ≤ B ≤ 0.2 wt%, even more preferably 0.02 wt% ≤ B ≤ 0.15 wt%, even more preferably 0.03 wt% ≤ B ≤ 0.1 wt%, most preferably 0.035 wt% ≤ B ≤ 0.07 wt%

[0099] In the above condition (2), B represents the content (weight%) of the trimer relative to the total weight of the isocyanate composition.

[0100] In addition, the isocyanate composition prepared in the first step may further include a compound represented by the following chemical formula 1, and the compound represented by the following chemical formula 1 is as described above.

[0101] [Chemical Formula 1]

[0102]

[0103] In the above chemical formula 1, B1 is -CH2-, -CH2CH2-, -CH2CH2CH2-, -CH2CH2CH2CH2- or -CH2CH2CH2CH2CH2-, preferably -CH2-, -CH2CH2- or -CH2CH2CH2-.

[0104] In addition, the compound represented by the above chemical formula 1 may be included in an amount of 200 ppm or less relative to the total weight of the isocyanate composition prepared in the first step.

[0105] Next, the second step of the storage method for the isocyanate composition of the present invention may 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 is storage stability reduced, but there may also be a problem where the optical lens manufactured using it becomes opaque due to an increase in haze, and / or the optical lens cannot be manufactured using it. If the storage humidity in the second step exceeds 1%RH, not only is storage stability reduced, but there may also be a problem where the optical lens manufactured using it becomes opaque due to an increase in haze.

[0106]

[0107] Meanwhile, the optical lens of the present invention may include the isocyanate composition of the present invention.

[0108]

[0109] Furthermore, the non-foam resin of the present invention may include the isocyanate composition of the present invention.

[0110] The non-foam resin of the present invention is a resin that does not have the shape of a foam and can be used for coatings, adhesives, sealants, or elastomers, but is not limited thereto.

[0111] As a specific example, the non-foam 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. As a preferred example of the active hydrogen group-containing component, it may be a raw material required to manufacture a polyurethane resin.

[0112] 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.

[0113]

[0114] Furthermore, the method for preparing the isocyanate composition of the present invention described above is explained as an example as follows.

[0115] Isocyanate compositions are synthesized by reacting an amine compound with phosgene in a solvent.

[0116] The solvents used in the above phosgenation reaction may 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, and two or more of these may be mixed and used.

[0117] 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 one or more 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, methylene diphenyl diamine, methylene dicyclohexyl diamine, toluene diamine, m-xylylene diamine, p-xylylene diamine and o-xylylene diamine, and salts thereof, and preferably may be m-xylylene diamine, p-xylylene diamine, o-xylylene diamine, or salts thereof.

[0118] The above amine compound may be included in an amount of 1 to 20 parts by weight per 100 parts by weight of solvent. If the content of the amine compound exceeds 20 parts by weight, there is a risk that a large amount of amine compound may precipitate. Preferably, it may be included in an amount of 1 to 15 parts by weight or 3 to 10 parts by weight.

[0119] Specifically, the phosgenation reaction may be carried out by a direct phosgenation method in which an amine compound is directly reacted with phosgene (Method 1); 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).

[0120] The direct phosgenation method of Method 1 above can be carried out by reacting an amine compound with phosgene in the organic solvent. At this time, the phosgene may be added in a lump sum at the beginning of the reaction, or a portion may be added at the beginning of the reaction, and the remainder may be added in portions during the reaction.

[0121] Meanwhile, the above method 1 may be carried out 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 completed and reacting. At this time, the first step is preferably carried out at a temperature of -15°C to -10°C to prevent leakage of highly toxic phosgene and to prevent rapid exothermic reaction when the amine compound is added, and the phosgeneization reaction in the second step may 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.

[0122] In the case of Method 2 above, the process can be carried out by reacting an amine compound with hydrochloric acid in an organic solvent to form an amine-hydrochloride compound, and then adding phosgene to react. The formation of the amine-hydrochloride compound can be carried out at a temperature of 30°C or lower, preferably about 23±5°C, and the reaction after the addition 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 is increased and thermal decomposition of the isocyanate is prevented, thereby enabling the production of a high-purity isocyanate compound in high yield.

[0123] In the case of Method 3 above, the process can be carried out by reacting an amine compound with carbonic acid in a solvent to form an amine-carbonate compound, and then adding phosgene to react. 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 addition of phosgene can be controlled to a temperature of 80°C to 180°C. Preferably, the temperature may 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 enabling the production of a high-purity isocyanate compound in a high yield.

[0124] After the reaction with phosgene is completed according to each method, a removal process such as nitrogen bubbling and a solvent removal process such as distillation for unreacted phosgene and hydrogen chloride gas may be optionally further performed, and these processes may be carried out according to conventional methods.

[0125]

[0126] The present invention will be explained in more detail below through examples, but the following examples are not intended to limit the scope of the invention and should be interpreted as being for the purpose of aiding understanding of the invention.

[0127]

[0128] Example 1: Preparation of an isocyanate composition

[0129] (1) 471 g of 1,2-dichlorobenzene and 32.5 g of m-xylylene diamine (m-XDA) with a purity of 99.4% were added into a reactor and stirred while injecting anhydrous hydrochloric acid at a rate of 20 g / hr at room temperature (23±5℃). During the process of injecting the anhydrous hydrochloric acid, the internal temperature of the reactor rose to 50℃.

[0130] (2) After injecting the anhydrous hydrochloric acid for 4 hours, the reactor was cooled until the internal temperature reached room temperature (23±5℃). Then, 43 ml of liquid phosgene was added to the reactor, and the reactor was heated until the internal temperature reached 130℃. During this time, from the time of phosgene addition until the time of reaction termination confirmation described later, a dry ice-acetone cooler was used to prevent the phosgene from leaking out. After the internal temperature of the reactor reached 130℃, the internal temperature of the reactor was maintained at 125 to 135℃ for 2 hours to make the solution inside the reactor transparent. By confirming that the reaction was terminated when the solution inside the reactor became transparent, it was confirmed that a reaction product with phosgene removed was produced inside the reactor.

[0131] (3) After that, nitrogen was blown into the reactor and the reactor was cooled until the internal temperature reached 80°C, and then the reaction product produced inside the reactor was obtained.

[0132] (4) The solvent contained in the reaction product obtained through vacuum distillation was removed, and a purification process was performed by distilling using a thin film distillation apparatus (TFE), followed by a vacuum purification process to remove the oligomer contained in the reaction product, thereby finally preparing an isocyanate composition. Purification using the thin film distillation apparatus (TFE) was performed under conditions of a feeding temperature of 150°C, a thin film distillation apparatus (TFE) temperature of 160°C, a vacuum of 0.6 torr, and a feeding rate of 20 ml / min, and then vacuum purification was performed under conditions of a pressure of 3.4 mbar and a temperature of 165°C.

[0133] Meanwhile, it was confirmed that the prepared isocyanate composition contains 1.20 wt% of a dimer relative to the total weight of the prepared isocyanate composition, 0.041 wt% of a trimer relative to the total weight of the prepared isocyanate composition, and 17 ppm of a compound represented by the following chemical formula 1-2 relative to the total weight of the prepared isocyanate composition.

[0134] [Chemical Formula 1-2]

[0135]

[0136] In the above chemical formula 1-2, B1 is -CH2-.

[0137]

[0138] Example 2: Preparation of an isocyanate composition

[0139] An isocyanate composition was prepared in the same manner as in Example 1. However, unlike in Example 1, purification using a thin-film distillation apparatus (TFE) was performed under conditions of a feeding temperature of 150°C, a thin-film distillation apparatus (TFE) temperature of 160°C, a vacuum of 0.4 torr, and a feeding rate of 30 ml / min, and then vacuum purification was performed under conditions of a pressure of 3.4 mbar and a temperature of 165°C to prepare the isocyanate composition.

[0140] Meanwhile, it was confirmed that the prepared isocyanate composition contains 1.03% by weight of the dimer relative to the total weight of the prepared isocyanate composition, 0.009% by weight of the trimer relative to the total weight of the prepared isocyanate composition, and 20 ppm of the compound represented by Chemical Formula 1-2 relative to the total weight of the prepared isocyanate composition.

[0141]

[0142] Example 3: Preparation of an isocyanate composition

[0143] An isocyanate composition was prepared in the same manner as in Example 1. However, unlike in Example 1, purification using a thin-film distillation apparatus (TFE) was performed under conditions of a feeding temperature of 150°C, a thin-film distillation apparatus (TFE) temperature of 160°C, a vacuum of 0.9 torr, and a feeding rate of 20 ml / min, and then vacuum purification was performed under conditions of a pressure of 3.4 mbar and a temperature of 165°C to prepare the isocyanate composition.

[0144] Meanwhile, it was confirmed that the prepared isocyanate composition contains 1.10 wt% of the dimer relative to the total weight of the prepared isocyanate composition, 0.38 wt% of the trimer relative to the total weight of the prepared isocyanate composition, and 23 ppm of the compound represented by Chemical Formula 1-2 relative to the total weight of the prepared isocyanate composition.

[0145]

[0146] Example 4: Preparation of an isocyanate composition

[0147] An isocyanate composition was prepared in the same manner as in Example 1. However, unlike in Example 1, purification using a thin-film distillation apparatus (TFE) was performed under conditions of a feeding temperature of 150°C, a thin-film distillation apparatus (TFE) temperature of 160°C, a vacuum of 0.9 torr, and a feeding rate of 20 ml / min, and then vacuum purification was performed under conditions of a pressure of 3.4 mbar and a temperature of 155°C to prepare the isocyanate composition.

[0148] Meanwhile, it was confirmed that the prepared isocyanate composition contains 2.0 wt% of a dimer relative to the total weight of the prepared isocyanate composition, 0.12 wt% of a trimer relative to the total weight of the prepared isocyanate composition, and 13 ppm of a compound represented by the chemical formula 1-2 relative to the total weight of the prepared isocyanate composition.

[0149]

[0150] Example 5: Preparation of an isocyanate composition

[0151] An isocyanate composition was prepared in the same manner as in Example 1. However, unlike in Example 1, purification using a thin-film distillation apparatus (TFE) was performed under conditions of a feeding temperature of 150°C, a thin-film distillation apparatus (TFE) temperature of 160°C, a vacuum of 0.3 torr, and a feeding rate of 10 ml / min, and then vacuum purification was performed under conditions of a pressure of 3.0 mbar and a temperature of 165°C to prepare the isocyanate composition.

[0152] Meanwhile, it was confirmed that the prepared isocyanate composition contains 1.30% by weight of a dimer and 0.05% by weight of a trimer based on the total weight of the prepared isocyanate composition, and does not contain the compound represented by Chemical Formula 1-2.

[0153]

[0154] Example 6: Preparation of an isocyanate composition

[0155] An isocyanate composition was prepared in the same manner as in Example 1. However, unlike in Example 1, purification using a thin-film distillation apparatus (TFE) was performed under conditions of a feeding temperature of 100°C, a thin-film distillation apparatus (TFE) temperature of 160°C, a vacuum of 0.6 torr, and a feeding rate of 30 ml / min to prepare the isocyanate composition.

[0156] Meanwhile, it was confirmed that the prepared isocyanate composition contains 1.2% by weight of the dimer relative to the total weight of the prepared isocyanate composition, 0.1% by weight of the trimer relative to the total weight of the prepared isocyanate composition, and 124 ppm of the compound represented by Chemical Formula 1-2 relative to the total weight of the prepared isocyanate composition.

[0157]

[0158] Comparative Example 1: Preparation of an isocyanate composition

[0159] An isocyanate composition was prepared in the same manner as in Example 1. However, unlike in Example 1, purification using a thin-film distillation apparatus (TFE) was performed under conditions of a feeding temperature of 140°C, a thin-film distillation apparatus (TFE) temperature of 150°C, a vacuum of 1.2 torr, and a feeding rate of 30 ml / min, and then vacuum purification was performed under conditions of a pressure of 3.8 mbar and a temperature of 160°C to prepare the isocyanate composition.

[0160] Meanwhile, it was confirmed that the prepared isocyanate composition contains 2.20 wt% of a dimer relative to the total weight of the prepared isocyanate composition, 0.33 wt% of a trimer relative to the total weight of the prepared isocyanate composition, and 318 ppm of a compound represented by the chemical formula 1-2 relative to the total weight of the prepared isocyanate composition.

[0161]

[0162] Experimental Example 1: Analysis of Components Included in the Isocyanate Composition

[0163] For the isocyanate compositions prepared in Examples 1 to 6 and Comparative Example 1, the content of dimers and trimers was confirmed through gel permeation chromatography (GPC) analysis, and the content of compounds represented by Chemical Formula 1-2 was confirmed through gas chromatography (GC) analysis. In addition, the analysis conditions for each are as follows.

[0164] <Gel Permeation Chromatography Analysis Conditions>

[0165] - Device used: Agilent

[0166] - Column: Agilent PL Mixded D, Agilent PLgel 100Å Agilent PLgel 50Å

[0167] - Sample concentration: 2 wt% / vol% (Prepared by dissolving 0.2 mg of sample in 9.8 ml of tetrahydrofuran)

[0168] - Carrier: THF

[0169] - Detection method: RI

[0170] - Flow rate: 1.0 ml / min

[0171] - Column temperature: 25℃

[0172] - Detector: Agilent RI detector

[0173] - When constructing the calibration curve, use polystyrene standard foam with a molecular weight of 104 to 24,600 g / mol.

[0174] <Gas Chromatography Analysis Conditions>

[0175] - Device used: Agilent 7890A

[0176] - Column; DB-17 (Inner diameter 0.25mm x Length 30m, Film 0.5㎛)

[0177] - Filtration filter; 0.45 µm Teflon filter

[0178] - Injection concentration; 1.0 mass%, dichloromethane solution

[0179] - Injection volume: 1 µl, Split ratio 100:1

[0180] - Injection temperature; 250℃

[0181] - Carrier gas; N21 mL / min

[0182] - Detector; FID

[0183] - Oven temperature: Hold at 80°C for 1 minute, increase from 80°C to 160°C at 5.0°C / min, hold for 8 minutes after reaching 160°C, increase from 160°C to 280°C at 20.0°C / min, hold for 18 minutes after reaching 280°C.

[0184]

[0185] Experimental Example 2: Haze Measurement

[0186] According to the method of ASTM E313, the haze of each isocyanate composition prepared in Examples 1 to 6 and Comparative Example 1 was measured (light source: C / 2) using HunterLab’s Ultrascan Pro and is shown in Table 1 below.

[0187] In addition, each of the isocyanate compositions prepared in Examples 1 to 6 and Comparative Example 1 was stored for 90 days under a nitrogen-substituted atmosphere, at a temperature of 15°C and a humidity of 0.1% RH, and then the haze of each of the stored isocyanate compositions prepared in Examples 1 to 6 and Comparative Example 1 was measured (light source: C / 2) and is shown in Table 1 below.

[0188]

[0189] As can be seen in Table 1, the isocyanate composition prepared in Example 1 had a low haze value, and it was confirmed to have excellent stability, especially having the lowest haze value after 90 days of storage.

[0190]

[0191] Preparation Examples 1 to 6 and Comparative Preparation Example 1: Preparation of optical lenses

[0192] A mixture was prepared by stirring and mixing 20.8 g of the isocyanate composition prepared in Examples 1 to 6 and Comparative Example 1, 0.04 g of ZELEC UN (Stepan) as an internal release agent, and 0.04 g of Biosorb 583 (Sakai Chemical Industry Co., Ltd) as a UV absorber for 20 minutes at room temperature (=23℃). To the prepared mixture, 0.24 g of a dye solution containing 0.047 wt% of Quinizarin Blue and 0.002 g of DBTC (dibutyltin dichloride) were added and stirred for 10 minutes. Then, 19.2 g of 2,3-bis(2-sulfanyl ethyl sulfanyl)propane-1-thiol was added, and the mixture was stirred for 1 hour while degassing under a pressure of 5 mbar to prepare a polyisocyanate polymerization composition.

[0193] The prepared polyisocyanate polymerization composition was filtered using a 1 μm PTFE filter and then poured into a mold consisting of a glass mold and a tape, respectively. Subsequently, the mold was placed in an oven, and the polymerization reaction was carried out for 20 hours while gradually increasing the temperature from 10°C to 120°C. After the polymerization was completed, the mold was removed from the oven and released to obtain each plastic optical lens. The obtained optical lenses were annealed at 120°C for 6 hours to produce each optical lens having a thickness of 9 mm. The optical lens prepared using the isocyanate composition prepared in Example 1 is shown as Preparation Example 1 in Table 2 below, the optical lens prepared using the isocyanate composition prepared in Example 2 is shown as Preparation Example 2 in Table 2 below, the optical lens prepared using the isocyanate composition prepared in Example 3 is shown as Preparation Example 3 in Table 2 below, the optical lens prepared using the isocyanate composition prepared in Example 4 is shown as Preparation Example 4 in Table 2 below, the optical lens prepared using the isocyanate composition prepared in Example 5 is shown as Preparation Example 5 in Table 2 below, the optical lens prepared using the isocyanate composition prepared in Example 6 is shown as Preparation Example 6 in Table 2 below, and the optical lens prepared using the isocyanate composition prepared in Comparative Example 1 is shown as Comparative Preparation Example 1 in Table 2 below.

[0194]

[0195] Experimental Example 3: Evaluation of Color and Cloudiness

[0196] (1) Color evaluation

[0197] For each of the optical lenses prepared in Preparation Examples 1 to 6 and Comparative Preparation Example 1, the color was evaluated visually, and the results are shown in Table 2 below.

[0198]

[0199] (2) Evaluation of turbidity

[0200] For each optical lens prepared in Examples 1 to 6 and Comparative Example 1, the degree of cloudiness was evaluated visually when irradiated with a fluorescent lamp and a zirconium lamp, respectively, as a light source, and the results are shown in Table 2 below. At this time, the evaluation criteria listed in Table 2 below were described as Clear when transparent when irradiated with both a fluorescent lamp and a zirconium lamp; Slightly lamp Haze when transparent when irradiated with a fluorescent lamp but some cloudiness is observed when irradiated with a zirconium lamp; Lamp Haze when transparent when irradiated with a fluorescent lamp but cloudiness is observed when irradiated with a zirconium lamp; and Visual Haze when cloudiness is observed when irradiated with both a fluorescent lamp and a zirconium lamp.

[0201]

[0202]

[0203] As can be seen in Table 2, it was confirmed that the optical lenses prepared in Examples 1 to 6 had superior chromaticity and opacity (=transparency) compared to the optical lens prepared in Comparative Example 1.

[0204]

[0205] Specific embodiments have been illustrated and described above. However, the invention is not limited to the aforementioned embodiments, and those skilled in the art may make various modifications without departing from the essence of the technical concept of the invention as described in the following claims.

Claims

1. A diisocyanate compound; a dimer; and a trimer; comprising, Isocyanate composition satisfying the following condition (1). (1) 0.2 wt% ≤ A ≤ 2.0 wt% In the above condition (1), A represents the content (weight%) of the dimer relative to the total weight of the isocyanate composition.

2. In Paragraph 1, The above isocyanate composition is an isocyanate composition that further satisfies the following condition (2). (2) 0.005 wt% ≤ B ≤ 0.3 wt% In the above condition (2), B represents the content (weight%) of the trimer relative to the total weight of the isocyanate composition.

3. In Paragraph 1, The above isocyanate composition further comprises 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-.

4. In Paragraph 3, An isocyanate composition comprising a compound represented by the above chemical formula 1 in an amount of 200 ppm or less based on the total weight of the isocyanate composition.

5. In Paragraph 4, The above isocyanate composition is an isocyanate composition that satisfies the following condition (3). (3) 0.1 ppm ≤ E ≤ 100 ppm In the above condition (3), E represents the content (ppm) of the compound represented by the above formula 1 with respect to the total weight of the isocyanate composition.

6. In Paragraph 1, The above diisocyanate compound comprises one or more 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, methylene diphenyl diisocyanate, methylene dicyclohexyl isocyanate, toluene diisocyanate, m-xylylene diisocyanate, p-xylylene diisocyanate, and o-xylylene diisocyanate, forming an isocyanate composition.

7. In Paragraph 1, The above diisocyanate compound is an isocyanate composition in which the diisocyanate compound is m-xylylene diisocyanate.

8. In Paragraph 3, An isocyanate composition in which 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-.

9. In Paragraph 1, The above isocyanate composition is an isocyanate composition that satisfies the following condition (4). (4) 0.001% ≤ D - C ≤ 0.2% In the above conditions (4), C represents the haze value of the isocyanate composition, and D represents the haze value measured after storing the isocyanate composition for 70 to 110 days at a temperature of 20°C or lower and a humidity of 1%RH or lower.

10. A first step of preparing an isocyanate composition comprising a diisocyanate compound, a dimer, and a trimer; 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; comprising, A storage method for an isocyanate composition satisfying the following condition (1). (1) 0.2 wt% ≤ A ≤ 2.0 wt% In the above condition (1), A represents the content (weight%) of the dimer relative to the total weight of the isocyanate composition.

11. In Paragraph 10, A method for storing an isocyanate composition, wherein the isocyanate composition prepared in the first step above further satisfies the following condition (2). (2) 0.005 wt% ≤ B ≤ 0.3 wt% In the above condition (2), B represents the content (weight%) of the trimer relative to the total weight of the isocyanate composition.

12. In Paragraph 10, A method for storing an isocyanate composition, wherein the isocyanate composition prepared in the first step above further comprises 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-.

13. In Paragraph 12, A method for storing an isocyanate composition, wherein the compound represented by the above chemical formula 1 is included in an amount of 200 ppm or less based on the total weight of the isocyanate composition prepared in the first step.

14. In Paragraph 10, The second step above 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.

15. An optical lens comprising the isocyanate composition of claim 1.

16. A non-form resin comprising the isocyanate composition of claim 1.

17. In Paragraph 16, The above non-foam resin is a non-foam resin for use as a coating agent, adhesive, sealant, or elastomer.

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