JP4606918B2 - Compositions containing stabilized aliphatic and / or alicyclic isocyanates - Google Patents

Description

  The present invention is an isocyanate that is suitably used as a raw material for urethane resins used not only for polyurethane foam, synthetic resins such as paints and adhesives, but also for optical resins such as eyeglass lenses that require high transparency. The present invention relates to the storage stability of a narate compound, particularly an aliphatic isocyanate compound.

  The isocyanate compound is a compound that is used in a very wide range as a raw material for urethane resin and is commercially produced on a huge scale, and its usefulness is high. However, it is difficult to maintain the stability of the isocyanate compound for a long time due to the extremely high reactivity exhibited by the isocyanate group, and there are cases where the compound is colored during long-term storage or causes white turbidity due to self-polymerization. Also, when the isocyanate compound packed in a container is extracted and used, the stability of the residual liquid in the container that has come into contact with air may be extremely reduced, and it is often necessary to pay great attention to handling. is there.

Numerous studies have been made for the purpose of stabilizing such isocyanate compounds, and various methods have been proposed. In general, stabilization is achieved by adding a stabilizer (for example, see Patent Documents 1 to 11). Among them, the stabilizer proposed in Patent Document 11 is more effective as a stabilizer than those proposed in other Patent Documents.
U.S. Pat. No. 3,715,381 Japanese Patent Publication No. 45-033438 Japanese Patent Laid-Open No. 50-036546 German Patent No. 2837770 U.S. Pat. No. 3,247,236 JP 50-101344 A JP 57-123159 A Japanese Unexamined Patent Publication No. 63-179917 JP-A-1-125359 JP-A-5-0783304 JP-A-9-087239

  However, in recent years, for isocyanate compounds used for applications requiring transparency such as optical material applications, it has been required to achieve higher levels of prevention of coloration and suppression of cloudiness. The coloring of isocyanate compounds and the suppression of white turbidity with stabilizers proposed in the prior art may not fully satisfy this high level requirement.

  As described above, the stabilizer proposed in Patent Document 11 is more effective as a stabilizer than those proposed in other Patent Documents, but it is still difficult to satisfy the above high level requirements. Met. In addition, depending on the lot of isocyanate compound produced, there may be a difference in the effect as a stabilizer, and it is difficult to predict the storage period and determine an appropriate addition amount.

  Therefore, the above high level requirements (for example, coloring in long-term storage for about one year, suppression of white turbidity due to self-polymerization, and repeated use of residual liquid in a container used halfway) In addition, there has been a demand for a method that can meet the target) and can stabilize the isocyanate compounds of different lots uniformly.

  In order to solve the above-mentioned problems, the present inventors have intensively studied the method for stabilizing an isocyanate compound by paying attention not only to the stabilizer but also to the isocyanate compound side. As a result, the inventors found that the storage stability and reproducibility of the isocyanate compound are remarkably improved by adjusting the acidity of the isocyanate component containing the isocyanate compound within a certain range.

That is, the first aspect of the present invention is
[1] An isocyanate component for transparent resin containing at least one aliphatic or alicyclic isocyanate compound, wherein the acidity in terms of HCl based on the total amount of the aliphatic or alicyclic isocyanate compound is The isocyanate component is 1 to 100 ppm.

Hereinafter, [2] to [10] are each one of preferred embodiments of the present invention.
[2] The above-mentioned [1] obtained by adjusting the acidity by adding a hydrogen halide gas and / or removing at least a part of the fraction obtained by performing a distillation operation. Isocyanate component [3] The aliphatic or alicyclic isocyanate compound is xylylene diisocyanate, 2,5-bis (isocyanatomethyl) bicyclo- [2,2,1] -heptane, 2,6 -Bis (isocyanatomethyl) bicyclo- [2,2,1] -heptane, 1,3-bis (isocyanatomethyl) cyclohexane, 1,6 diisocyanatohexane, isophorone diisocyanate, and methylenebis (4,1 -Cyclohexylene) The isocyanate component according to [1] or [2] above, which is one or more compounds selected from diisocyanates.
[4] The isocyanate component according to the above [3], wherein the aliphatic and / or alicyclic isocyanate compound is xylylene diisocyanate.
[5] A composition for transparent resin obtained using the isocyanate component according to any one of [1] to [4].
[6] The composition for transparent resin as described in [5] above, which contains polythiol and / or polyol.
[7] The composition for transparent resin according to [5] or [6], which is for optical materials.
[8] An optical material produced using the composition according to the above [7].
[9] A method for producing a plastic lens using the composition according to the above [7].
[10] A plastic lens made of the optical material according to [8]. Here, “consisting of” includes both the case where the entire plastic lens is made of the optical material and the case where a part of the plastic lens is made of the optical material. It is the purpose.

The second aspect of the present invention is:
[11] The acidity in terms of HCl based on the total amount of the aliphatic or alicyclic isocyanate compound of the isocyanate component for transparent resin containing at least one aliphatic or alicyclic isocyanate compound, A method of adjusting to 1 to 100 ppm by adding hydrogen fluoride gas and / or removing at least a part of the fraction obtained by performing a distillation operation.

  The present invention has enabled the stabilization of isocyanate compounds at higher levels. As a result, conventional problems such as coloring due to aging and generation of white turbidity due to contact with slight air are improved, and the storage period is extended, for example, if not handled under a strict nitrogen atmosphere. It can be expected that the yield, which has been reduced by the above, will be greatly improved. In addition, the necessity of a strict nitrogen atmosphere at each stage from production to disposal of the isocyanate compound has been alleviated, and it has become possible to handle the isocyanate compound more easily.

  Hereinafter, the present invention will be described in detail. A first aspect of the present invention is an isocyanate component for a transparent resin containing at least one aliphatic or alicyclic isocyanate compound, and is based on the total amount of the aliphatic or alicyclic isocyanate compound. It is an isocyanate component whose acidity is 1 to 100 ppm in terms of HCl.

  The isocyanate component which is the first form of the present invention contains at least one aliphatic or alicyclic isocyanate compound. That is, the aliphatic or alicyclic isocyanate compound contained in the isocyanate component may be a single type or a combination of two or more types. In the case of a combination of two or more, it may be a combination of aliphatic isocyanate compounds, a combination of alicyclic isocyanate compounds, or an aliphatic isocyanate compound and A combination with an alicyclic isocyanate compound may also be used.

  The isocyanate component which is the 1st form of this invention is used in order to polymerize with other components, such as polythiol, and to manufacture a transparent resin.

  The isocyanate compound used in the isocyanate component according to the first aspect of the present invention is a compound having at least one isocyanate group in the molecule. The object of stabilization according to the present invention is an aliphatic or alicyclic group in which an isocyanato group is bonded to an aliphatic skeleton hydrocarbon group or an alicyclic skeleton hydrocarbon group from the viewpoint of the reactivity of the isocyanato group of the compound. Isocyanate. As used herein, the aliphatic or alicyclic isocyanate only needs to have an isocyanate group bonded to the aliphatic skeleton hydrocarbon group or alicyclic skeleton hydrocarbon group, and has an aromatic ring at other positions. May be.

Specific examples of the aliphatic or alicyclic isocyanate compound in the present invention include, for example, monoisocyanate compounds such as butyl isocyanate and benzyl isocyanate, which are compounds having one isocyanate group in the molecule, Hexamethylene diisocyanate, 2,2-dimethylpentane diisocyanate, 2,2,4-trimethylhexane diisocyanate, butene diisocyanate, which are compounds having two or more isocyanate groups in the molecule, 3-butadiene-1,4-diisocyanate, 2,4,4-trimethylhexamethylene diisocyanate, 1,6,11-undecatriisocyanate, 1,3,6-hexamethylene triisocyanate, 1, 8-diisocyanato-4-isocyanatomethyloctane, bis (isocyana Ethyl) carbonate, bis (isocyanatoethyl) ether, lysine diisocyanate methyl ester, lysine triisocyanate, xylylene diisocyanate, bis (isocyanatoethyl) benzene, bis (isocyanatopropyl) benzene, α, α, α ', Α'-tetramethylxylylene diisocyanate, bis (isocyanatobutyl) benzene, bis (isocyanatomethyl) naphthalene, bis (isocyanatomethyl) diphenyl ether, bis (isocyanatoethyl) phthalate, mesityrylene triisocyanate Aliphatic polyisocyanates such as 2,6-di (isocyanatomethyl) furan,
Isophorone diisocyanate, bis (isocyanatomethyl) cyclohexane, methylenebis (4,1-cyclohexylene) diisocyanate, cyclohexane diisocyanate, methylcyclohexane diisocyanate, dicyclohexyldimethylmethane diisocyanate, 2,2-dimethyl Dicyclohexylmethane diisocyanate, 2,5-bis (isocyanatomethyl) bicyclo- [2,2,1] -heptane, 2,6-bis (isocyanatomethyl) bicyclo- [2,2,1] -heptane, 3,8-bis (isocyanatomethyl) tricyclodecane, 3,9-bis (isocyanatomethyl) tricyclodecane, 4,8-bis (isocyanatomethyl) tricyclodecane, 4,9-bis (isocyanato) Aliphatic polyiso, such as methyl) tricyclodecane Annatto,
Bis (isocyanatomethyl) sulfide, bis (isocyanatoethyl) sulfide, bis (isocyanatopropyl) sulfide, bis (isocyanatohexyl) sulfide, bis (isocyanatomethyl) sulfone, bis (isocyanatomethyl) disulfide, bis ( Isocyanatoethyl) disulfide, bis (isocyanatopropyl) disulfide, bis (isocyanatomethylthio) methane, bis (isocyanatoethylthio) methane, bis (isocyanatoethylthio) ethane, bis (isocyanatomethylthio) ethane, 1, 5-diisocyanato-2-isocyanatomethyl-3-thiapentane, 2,5-diisocyanatotetrahydrothiophene, 2,5-bis (isocyanatomethyl) tetrahydrothiophene, 3,4-bis (isocyanatomethyl) ) Tetrahydrothiophene, 2,5-diisocyanato-1,4-dithiane, 2,5-bis (isocyanatomethyl) -1,4-dithiane, 4,5-diisocyanato-1,3-dithiolane, 4,5-bis Sulfur-containing aliphatic isocyanates such as (isocyanatomethyl) -1,3-dithiolane, 4,5-bis (isocyanatomethyl) -2-methyl-1,3-dithiolane,
Other examples include sulfur-containing heterocyclic compounds such as 2,5-diisocyanatothiophene and 2,5-bis (isocyanatomethyl) thiophene, but are not limited to these exemplified compounds. Among these exemplified compounds, compounds in which the stabilizing effect is particularly remarkable include xylylene diisocyanate, 2,5-bis (isocyanatomethyl) bicyclo- [2,2,1] -heptane, 2,6-bis. (Isocyanatomethyl) bicyclo- [2,2,1] -heptane, 1,3-bis (isocyanatomethyl) cyclohexane, 1,6-diisocyanatohexane, isophorone diisocyanate, and methylenebis (1,4- (Cyclohexylene) diisocyanate and the like, and the effect on xylylene diisocyanate is particularly great.

  The isocyanate component which is the first form of the present invention may contain a substance other than the aliphatic or alicyclic isocyanate compound as long as the object of the present invention is not realized.

  The “acidity” in the isocyanate component according to the first embodiment of the present invention is a value obtained by converting the amount of acidic component that reacts with alcohol at room temperature and is liberated into HCl. The ratio of the amount of the acid component converted to HCl to the total amount of the aliphatic or alicyclic isocyanate compound is represented by a weight ratio. Within the scope of the present invention, it is convenient to mark in ppm. The acidity can be measured by titration with an inorganic base such as KOH. More specifically, the acidity is usually measured by the method shown in Examples.

  As described above, since the acidity of the isocyanate component is defined based on the total amount of the aliphatic or alicyclic isocyanate compound, it is affected by the presence of a substance other than the aliphatic or alicyclic isocyanate compound. I do not receive it.

  Since the isocyanate component according to the first embodiment of the present invention has an acidity of 1 ppm or more, a stabilizing effect can be sufficiently expected, which is preferable. The acidity is more preferably 2 ppm or more, and further preferably 5 ppm or more. In addition, since the acidity is 100 ppm or less, the deterioration and coloring of the isocyanate compound is suppressed, or the necessity for changing the production conditions of the synthetic resin using the isocyanate composition mixed with the stabilizer is small, and the synthetic resin itself This is preferable since the deterioration of the performance, particularly the hue and weather resistance, is suppressed. More preferably, it is 90 ppm or less. If it is 80 ppm or less, it is still more preferable. In any case, it is preferable to adjust the addition amount according to the type of isocyanate compound to be stabilized, the required storage period and storage conditions.

  In addition, the isocyanate component containing the aliphatic or alicyclic isocyanate compound of the present invention is an essential requirement that the acidity is in the range of 1 to 100 ppm, as long as the stabilizing effect of the present invention is not hindered. It does not matter at all if it contains an additive usually used for an isocyanate compound. In particular, some compounds among the stabilizers described in Patent Documents 1 to 11 described above are used in combination with the stabilization according to the first aspect of the present invention, whereby the stabilization effect increases synergistically. There is also preferred.

  A transparent resin can be prepared by polymerizing the isocyanate component which is the first embodiment of the present invention and other components. That is, the composition obtained by using the isocyanate component which is the first embodiment of the present invention is preferable as the composition for transparent resin because it is excellent in the stability of the isocyanate component.

  The other components used in combination with the isocyanate component are not particularly limited, but preferably include an active hydrogen group-containing compound. In view of the properties of the resulting resin, the polythiol and / or polyol It is particularly preferable that it is included. That is, the transparent resin composition containing the isocyanate component and the polythiol and / or polyol which is the first embodiment of the present invention is particularly preferable as an embodiment of the present invention.

  The polythiol and polyol preferably used in the present invention are not particularly limited, and any compound having two or more mercapto groups and / or hydroxyl groups in one molecule can be suitably used. For example, various polythiols represented by polythiol described in JP-A Nos. 64-90168 and 64-90169 can be used as appropriate.

  The composition for transparent resin, which is a preferred embodiment of the present invention, is a polymerization component other than those described above (for example, a compound having a polymerizable unsaturated group, a compound having an episulfide group, an epoxy group, as long as the object of the present invention is not impaired. And other additives (light stabilizers, ultraviolet absorbers, antioxidants, anti-coloring agents, etc.) and the like.

  Many transparent resins obtained by polymerizing a polymerizable composition which is one of the preferred embodiments of the present invention are excellent in optical properties such as transparency and refractive index. Therefore, the use of the transparent resin composition that is one of the preferred embodiments of the present invention for an optical material, and the optical material produced using such a composition are both preferred embodiments of the present invention. It is one of. Such an optical material can be obtained in various shapes, and can be used for various applications as an optical material used for spectacle lenses, camera lenses, light emitting diodes (LEDs), light guide plates, optical fibers, prisms, and the like. Is possible. In particular, it is suitable for optical materials and optical elements such as eyeglass lenses, camera lenses, and light emitting diodes.

  Many of the above optical materials have excellent characteristics required for lenses such as transparency, refractive index, and Abbe number. Therefore, a method for producing a plastic lens using the above-mentioned composition for transparent resin and a plastic lens made of the above optical material are both preferred embodiments of the present invention.

  As a plastic lens, a polythiourethane resin in which a sulfur atom is introduced into the resin is known. Polythiourethane resin is a well-balanced resin such as high refractive index and good impact resistance. For example, various polythiourethane resins represented by resins described in JP-A-63-46213 are used for plastic lenses. Therefore, taking a plastic lens made of polythiourethane resin as an example, a method for producing a plastic lens and a plastic lens, which are preferred embodiments of the present invention, will be described.

  The plastic lens which is a preferred embodiment of the present invention is usually obtained by cast polymerization. The isocyanate component and the polythiol component are mixed, and the mixed solution is defoamed by an appropriate method if necessary, and then poured into a mold and polymerized while gradually raising the temperature normally from a low temperature to a high temperature. The polymerization temperature and time vary depending on the composition of the monomer, the type and amount of the additive, and cannot be determined in general. By heating, the resin is cured and the resin can be taken out.

  As the curing catalyst used in the present invention, tertiary amines, phosphines, quaternary ammonium salts, quaternary phosphonium salts, Swiss acids, radical polymerization catalysts, and cationic polymerization catalysts are usually used, but are not limited thereto. is not.

  Specific examples of the curing catalyst include triethylamine, tri-n-butylamine, tri-n-hexylamine, N, N-diisopropylethylamine, triethylenediamine, triphenylamine, N, N-dimethylethanolamine, N, N- Diethylethanolamine, N, N-dibutylethanolamine, N, N-dimethylbenzylamine, diethylbenzylamine, N, N-dimethylcyclohexylamine, N, N-diethylcyclohexylamine, N-methyldicyclohexylamine, N-methylmori Folin, N-isopropylmorpholine, pyridine, N, N-dimethylaniline, β-pyridone, N, N′-dimethylpiperazine, N-methylpiperidine, 2,2′-bipyridyl, hexamethylenetetramine, 1,8-diazabicyclo ( 5,4,0) -7-U Tertiary amines such as decene, trimethylphosphine, triethylphosphine, tri-n-propylphosphine, triisopropylphosphine, tri-n-butylphosphine, triphenylphosphine, tribenzylphosphine, 1,2-bis (diphenylphosphino) Phosphines such as ethane, 1,2-bis (dimethylphosphino) ethane, quaternary ammonium salts such as tetramethylammonium bromide, tetrabutylammonium chloride, tetrabutylammonium bromide, tetramethylboronium bromide, tetrabutylboronium chloride , Quaternary boronium salts such as tetrabutyl boronium bromide, dimethyltin dichloride, dibutyltin dichloride, dibutyltin dilaurate, tetrachlorotin, dibutyltin Lewis acids such as oxide, diacetoxytetrabutyl distanoxane, zinc chloride, acetylacetone zinc, aluminum chloride, aluminum fluoride, triphenylaluminum, tetrachlorotitanium, calcium acetate, 2,2′-azobis (2-cyclopropylpro Piononitrile), 2,2′-azobis (4-methoxy-2,4-dimethylvaleronitrile), 2,2′-azobis (2,4-dimethylvaleronitrile), t-butylperoxy-2-ethylhexanoate Radical polymerization agents such as n-butyl-4,4′-bis (t-butylperoxy) valerate, t-butylperoxybenzoate, diphenyliodonium hexafluorophosphoric acid, diphenyliodonium hexafluoroarsenic acid, diphenyliodonium hexafluoroantimony, Triphenylphospho Cationic polymerization catalysts such as nium hexafluoroboric acid, triphenylphosphonium hexafluorophosphoric acid, and triphenylsulfonium hexafluoroarsenic acid may be mentioned, but the present invention is not limited to these exemplified compounds.

  Among these exemplified compounds, preferred are organic tin compounds such as dimethyltin dichloride, dibutyltin dichloride, dibutyltin dilaurate, tetrachlorotin, dibutyltin oxide, and diacetoxytetrabutyldistanoxane. The above curing catalysts may be used alone or in combination of two or more, but when two or more kinds of curing catalysts having different activities are used in combination, the hue of the resulting resin is improved or optical distortion (pulse separation) is suppressed. It is desirable to select the combination appropriately.

  In the resin molding of the present invention, a chain extender, a crosslinking agent, a light stabilizer, an ultraviolet absorber, an antioxidant, an anti-coloring agent, a dye, a filling, and the like in the known molding method according to the purpose. Various substances such as an agent, an external or internal mold release agent, and an adhesion improver may be added.

  Furthermore, in the plastic lens which is a preferred embodiment of the present invention, if necessary, antireflection, imparting high hardness, improving wear resistance, improving chemical resistance, imparting antifogging, surface polishing, antistatic treatment, hard Physical or chemical treatment such as coating treatment, non-reflective coating treatment, and dyeing treatment can be performed.

  Then, the adjustment method of the acidity of the isocyanate component which is the 2nd form of this invention is demonstrated. According to a second aspect of the present invention, HCl based on the total amount of the aliphatic or alicyclic isocyanate compound of the isocyanate component for transparent resin containing at least one aliphatic or alicyclic isocyanate compound is used. This is a method of adjusting the converted acidity to 1 to 100 ppm by adding a hydrogen halide gas and / or performing a distillation operation and removing at least a part of the fraction obtained thereby.

  The meanings of “aliphatic or alicyclic isocyanate compound” and “acidity” in the second embodiment of the present invention are the same as those in the first embodiment of the present invention.

  In the second embodiment of the present invention, the hydrogen halide that can be used for adjusting the acidity is not particularly limited as long as it is a compound having halogen and hydrogen, and any compound can be used. Preferable specific examples include hydrogen fluoride, hydrogen chloride, hydrogen bromide, hydrogen iodide and the like. Of these, hydrogen chloride is preferable in view of handling.

  The hydrogen halide that can be used in the present invention is not necessarily special, and a commercially available inorganic acid can be preferably used. The compound is preferably low in impurities, and is preferably filled in a cylinder so that moisture, oxygen, and the like are not mixed during use.

  In the second embodiment of the present invention, as a method of mixing hydrogen halide into an isocyanate component containing an aliphatic or alicyclic isocyanate compound, for example, a gas feed pipe is installed in the liquid of the isocyanate component. And a certain amount of gas can be fed directly from the feed pipe. At that time, it is more preferable if the tip of the gas feed tube has a porous shape such as a filter (a shape in which gas can be finely sprayed). It is widely carried out as a normal operation that the liquid is made uniform by blowing or stirring while blowing a certain amount of gas.

  Conversely, when using an isocyanate component containing an aliphatic and / or alicyclic isocyanate compound with high acidity, perform distillation operation and cut all or part of the initial fraction appropriately. It is possible to reduce the acidity, which is a preferable treatment in such a case.

  The isocyanate component containing the aliphatic and / or alicyclic isocyanate compound after being adjusted according to the second aspect of the present invention is the first aspect of the present invention, except for the limitation of the adjustment method. This is the same as the isocyanate component. Since the acidity of the isocyanate component containing the aliphatic and / or alicyclic isocyanate compound prepared according to the second aspect of the present invention is 1 ppm or more, a sufficient stabilizing effect can be expected, which is preferable. The acidity is more preferably 2 ppm or more, and further preferably 5 ppm or more. Further, since the acidity is 100 ppm or less, the deterioration and coloring of the isocyanate compound is suppressed, or the necessity for changing the production conditions of the transparent resin using the isocyanate composition mixed with the stabilizer is small, and the transparent resin itself The performance, particularly the hue and weather resistance, are preferably suppressed. The acidity is more preferably 90 ppm or less. If it is 80 ppm or less, it is still more preferable. In any case, it is preferable to adjust the addition amount according to the type of isocyanate compound to be stabilized, the required storage period and storage conditions.

  In addition, the isocyanate component containing the aliphatic or alicyclic isocyanate compound prepared according to the second embodiment of the present invention is required to have an acidity in the range of 1 to 100 ppm. As long as the stabilizing effect is not hindered, other additives usually used in isocyanate compounds may be contained. In particular, some compounds among the stabilizers described in Patent Documents 1 to 11 described above are used in combination with a hydrogen halide that can be used in the present invention, and the stabilization effect increases synergistically. There is also preferred.

[Example]
Hereinafter, the effects of the present invention will be specifically described with reference to Examples and Comparative Examples, but the present invention is not limited to these Examples.
(Evaluation of isocyanate) The acidity and stability in Examples 1 to 4 and Comparative Examples 1 to 4 were evaluated according to the following test methods.
Coloring: According to the hue APHA method of JIS K-1556.
-Turbidity: The sample was placed in a colorless and transparent glass container, and turbidity was confirmed under the fluorescent lamp and through the light of the slide projector lamp. The case where turbidity was seen under a fluorescent lamp was marked with △ when the turbidity was seen through a slide projector, and the case where no turbidity was seen even when seen through a slide projector.
Acidity: Weigh accurately 20 g of sample in a 200 ml beaker containing a stir bar, add 100 ml of a solvent (a mixture of acetone and ethanol at a ratio of 1: 1 (volume ratio)), place on a hot plate and heat. After dissolving the sample, the mixture is allowed to react while stirring at room temperature for 10 to 20 minutes. Next, N / 100 methanolic potassium hydroxide solution (according to JIS K4101, adjusted and standardized with methanol, 0.1 mol / L methanolic potassium hydroxide accurately diluted 10 times using an automatic measuring device is prepared. The end point is the inflection point of the titration curve obtained by the titration in (1). In addition, this test is a blank test under the same conditions. From the titration result, acidity (%) is calculated according to the following formula.

A: Amount (ml) of N / 100 methanolic potassium hydroxide solution required for titration of the sample
B: Use amount of N / 100 methanolic potassium hydroxide solution required for the blank test (ml)
f: Factor of N / 100 methanolic potassium hydroxide solution S: Weight of sample (g)
・ Measurement equipment Automatic titrator: Hiranuma COM-500
[Example 1]
Purity 99.8% or more, hue (APHA) 10, transparency (no turbidity through projector lamp light), good quality m-xylylene diisocyanate, hydrogen chloride gas is added, acidity is 80 ppm It was adjusted. This m-xylylene diisocyanate was sealed in a brown bottle filled with nitrogen gas to obtain a measurement sample. A total of 5 or more samples were prepared and stored at 40 ° C. to conduct a stability test. At the end of 10 weeks after the start of the test, one of the samples was opened and the coloring and turbidity were evaluated. Thereafter, each time 10 weeks passed, one sample was opened, and coloring and turbidity were evaluated. The stability test was continued until 50 weeks had passed since the start. The test results are shown in Table 1.
[Examples 2-3]
A sample was prepared and a stability test was conducted in the same manner as in Example 1 except that the addition amount of hydrogen chloride gas was changed and the acidity was 20 ppm and 1 ppm, respectively. The test results are shown in Table 1.
[Comparative Examples 1-3]
A sample was prepared and a stability test was performed in the same manner as in Example 1 except that the addition amount of hydrogen chloride gas was changed and the acidity was set to 200 ppm, 120 ppm, and 0.1 ppm, respectively. The test results are shown in Table 1.
[Example 4]
A sample was prepared in the same manner as in Example 1 except that the acidity was 20 ppm. In the same manner as in Example 1, the sample was stored at 40 ° C. and subjected to a stability test for 50 weeks, and sampling, coloring and turbidity were evaluated every 10 weeks.

  However, in this example, sampling was performed from the same sample (bottle), and every time it was opened and sampled, it was sufficiently purged with nitrogen, sealed again, and stored again. Furthermore, opening, sampling operation, nitrogen purging, and sealing were performed at the start of the test (week 0).

The test results are shown in Table 1.
[Comparative Example 4]
A sample was prepared and a stability test was performed in the same manner as in Example 4 except that the acidity was 0.1 ppm. The test results are shown in Table 1.

(Evaluation of resin)
Of the m-xylylene diisocyanate used in the above storage test, a resin was prepared using the one at the start (0 week) and the end (50 weeks) of the storage test. The hue, turbidity and weather resistance of the obtained resin were evaluated. The evaluation method is as follows.
-Residual turbidity: The resin was visually recognized through the light of the slide projector lamp. The turbidity was evaluated as x, and the turbidity was determined as o.
-Resin hue: The yellow index (YI) of the resin was measured using a color difference meter. A sample having a YI of less than 5 was evaluated as ◯, and a sample having a YI of 5 or more was evaluated as ×.
-Weather resistance: Using a carbon arc fade meter, the obtained resin was put on a test machine for 20 hours. The one with large discoloration was x, the one with slight discoloration was △, and the one with little discoloration. ○.
[Example 5]
Dissolve in 18.2 g of m-xylylene diisocyanate used in Example 1 by adding 10 mg of dibutyltin dichloride as a polymerization catalyst, 30 mg of trade name biosorb583 as a UV absorber, and 40 mg of trade name ZelecUN as an internal mold release agent. Subsequently, 16.8 g of 1,8-dimercapto-4- (mercaptomethyl) -3,6-dithiaoctane was added, and the mixture was deaerated for 1 hour while mixing at a vacuum degree of 0.4 kPa. After degassing, the product was filtered using a Teflon (registered trademark) filter, and the filtered filtrate was poured into a mold comprising a gasket and a glass plate. Subsequently, the mold mold after injection was set in an oven, and polymerization was performed by raising the temperature from 25 ° C. to 120 ° C. in 20 hours. After completion of the polymerization, the temperature in the oven was returned to room temperature, and the resin (flat plate shape) was taken out of the mold. The obtained resin was evaluated for turbidity, hue, and weather resistance according to the above method, and the results are shown in Table 2.
[Examples 6 to 8]
In Example 5, in place of the m-xylylene diisocyanate used in Example 1, m-xylylene diisocyanate used in Examples 2 to 4 was used. Fabrication and evaluation were performed. The evaluation results are shown in Table 2.
[Comparative Examples 6-8]
In Example 5, instead of the m-xylylene diisocyanate used in Example 1, the m-xylylene diisocyanate used in Comparative Examples 1 to 4 was used under the same conditions as in Example 5 except that Fabrication and evaluation were performed. The evaluation results are shown in Table 2.

Claims (8)

An isocyanate component for a transparent resin containing at least one aliphatic or alicyclic isocyanate compound, wherein the HCl-based acidity based on the total amount of the aliphatic or alicyclic isocyanate compound is 1 to A transparent resin composition for optical materials, obtained using an isocyanate component that is 100 ppm. The isocyanate component was obtained by adjusting the acidity by adding hydrogen halide gas and / or removing at least a part of the fraction obtained by performing a distillation operation. Item 2. A transparent resin composition for an optical material according to Item 1. The aliphatic or alicyclic isocyanate compound is xylylene diisocyanate, 2,5-bis (isocyanatomethyl) bicyclo- [2,2,1] -heptane, 2,6-bis (isocyanatomethyl) bicyclo- From [2,2,1] -heptane, 1,3-bis (isocyanatomethyl) cyclohexane, 1,6 diisocyanatohexane, isophorone diisocyanate, and methylenebis (4,1-cyclohexylene) diisocyanate The transparent resin composition for optical materials according to claim 1, which is one or more selected compounds. The transparent resin composition for an optical material according to claim 3, wherein the aliphatic or alicyclic isocyanate compound is xylylene diisocyanate. The transparent resin composition for optical materials according to any one of claims 1 to 4, comprising polythiol and / or polyol. An optical material produced using the composition according to claim 1 . A method for producing a plastic lens using the composition according to claim 1 . A plastic lens comprising the optical material according to claim 6 .