JP3029603B2 - Optical products - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION The present invention relates to an optical chemical products,
More specifically, high refractive index, low dispersion, excellent transparency,
In addition to excellent optical characteristics such as no optical distortion, heat resistance,
Solvent resistance, weatherability good, lenses, prisms, optical fibers, a recording medium substrate, filter, or even those glasses, an optical products such as flowers bottle.

[0002]

2. Description of the Related Art Compared with glass, plastics are lighter, harder to break, and easier to dye. Therefore, plastics have recently been used for optical applications such as various lenses. As an optical plastic material, polyethylene glycol bisallyl carbonate (CR-39) or polymethyl methacrylate (PMMA) is generally used. However,
Since these plastic materials have a refractive index of 1.5 or less, for example, when used as a lens material, the greater the power, the greater the thickness of the lens must be, and the superiority of lightweight plastics is impaired. Not only was it not good, but it was not desirable in terms of aesthetics. In particular, in the case of a concave lens, the thickness (edge thickness) around the lens is increased, and there is a problem that birefringence and chromatic aberration are likely to occur.

[0003] In order to make the thickness of the lens thinner by making use of the characteristics of plastic having a small specific gravity,
A plastic material having a high refractive index has been desired. Examples of materials having such performance include (1) a polymer comprising a xylylene diisocyanate compound and a polythiol compound (JP-A-63-46213), and (2)
Resin consisting of aliphatic linear sulfur-containing bifunctional isocyanate compound and polythiol compound (JP-A-2-153302)
And (3) a polymer comprising an aliphatic branched sulfur-containing bifunctional isocyanate compound and a polythiol compound (JP-A-10-45707).

[0004] However, the polymer (1) and the resin (2) have a high refractive index by limiting the combination with the polythiol compound as a polymerization partner. There is a problem that the number decreases and chromatic aberration increases, and in (2), a problem occurs that heat resistance deteriorates. on the other hand,
The polymer of (3) has a high refractive index and is improved in terms of chromatic aberration and heat resistance. However, the heat resistance is still not sufficiently satisfactory and the solvent resistance is poor.

Further, since these are uncrosslinked polymers obtained from bifunctional isocyanate compounds, a special crosslinking agent is required separately in order to improve heat resistance, solvent resistance and the like. However, there is a problem that the kind of the polythiol compound is inevitably restricted.

[0006]

Under these circumstances, the present invention provides excellent optical characteristics such as high refractive index, low dispersion, excellent transparency, and no optical distortion, as well as heat resistance. it is intended to solvent resistance, providing weatherability good light chemical products intended.

[0007]

Means for Solving the Problems The inventors of the present invention have conducted intensive studies to develop an optical product having the above-mentioned preferable properties, and as a result, a component containing a specific polyisocyanate compound and a hydroxyl group in one molecule. Alternatively, they have found that an optical product made of poly (thio) urethane obtained by a polyaddition reaction with a component containing a compound having two or more mercapto groups or both of them can be suitable for the purpose. Thus, the present invention has been completed.

That is, the present invention relates to (A) a compound represented by the general formula (I)

Embedded image (Wherein, Z represents a direct bond or —CH ₂ — ), a component containing at least a polyisocyanate compound represented by the formula (B) (A), a compound having two or more mercapto groups in one molecule, (B) containing at least one compound selected from among compounds having two or more hydroxyl groups in one molecule and (c) compounds having one or more hydroxyl groups and one or more mercapto groups in one molecule An optical product comprising a poly (thio) urethane obtained by subjecting a monomer mixture containing a component to a polyaddition reaction.

[0009]

DETAILED DESCRIPTION OF THE INVENTION The optical product of the present invention is a poly (thio)
The component (A), which is made of urethane and is one of the raw materials for the poly (thio) urethane, has a general formula (I)

Embedded image What contains the polyisocyanate compound represented by these is used. The polyisocyanate compound has a basic skeleton of a structure branched from the 3-position of a 2,4-dithiapentylene group and has three isocyanate groups.

In the general formula (I), Z is a direct bond
Or —CH ₂ —.

As described above, since the polyisocyanate compound represented by the general formula (I) contains a sulfur atom in the basic skeleton, the refractive index and Abbe number of the polyisocyanate compound itself can be increased. when manufacturing an optical product with its optical Ltd.
Also increase the refractive index and Abbe number of the product . In addition, since this polyisocyanate compound has three isocyanate groups, it itself becomes a crosslinking agent. Therefore, when an optical product is manufactured using this polyisocyanate compound,
The optical product can be provided with high heat resistance, high solvent resistance, and excellent mechanical properties without adding another crosslinking agent as an accessory component.

As described above, by using the polyisocyanate compound represented by the general formula (I), it is not necessary to use a crosslinking agent, but a crosslinking agent can be used together if necessary. Specific examples of the polyisocyanate compound represented by the general formula (I) include those having the following structures.

[0013]

Embedded image As a production method of this general formula (I) polyisocyanate compound represented by may be any method that polyisocyanate compound having a desired structure can be obtained, is not particularly limited, the production method 1 and 2 below If it follows, it can manufacture very efficiently.

[0014] Production Method 1: production method 1, Z is the formula (I), a direct bond or
Or a method for producing a polyisocyanate compound which is —CH ₂ — .

In this production method 1, first, general formula (III) X ₂ -Y-COOR ¹ ... (III) (where X is a halogen atom, Y is は CH— or ＝ CH
CH ₂ — and R ¹ represent a lower alkyl group. Reaction of the lower alkyl dihalogenoaliphatic carboxylic acid with the lower alkyl thioglycolate to give a compound of the general formula (IV)

Embedded image (Wherein, R ² represents a lower alkyl group, and Y and R ¹ are the same as described above).

In this reaction, in the presence of a hydrogen halide scavenger, substantially 2 moles of a lower alkyl thioglycolic acid ester per mole of a lower alkyl ester of a dihalogenofatty acid carboxylic acid represented by the general formula (III) are added. It is good to react. In this case, an appropriate solvent can be used if necessary.

Next, the thus obtained general formula (I
The tricarboxylic acid ester represented by V) is reacted with hydrazine monohydrate or the like to give a compound of the general formula (V)

Embedded image (Wherein, Y is the same as described above). At this time, if necessary, a solvent such as a lower alcohol can be used.

Finally, the thus-obtained tricarbonylhydrazide represented by the general formula (V) is reacted with, for example, nitrous acid in an aqueous solution of hydrochloric acid, and then subjected to a heat transfer to form a carbonylhydrazide group. By converting into an isocyanate group, the desired general formula (Ia)

Embedded image (Wherein, Y is the same as described above).

Production method 2 : Production method 2 is a method for producing 1,5-diisocyanato-3-isocyanatomethyl-2,4-dithiapentane wherein Z in the general formula (I) is --CH _2-. is there.
This compound can also be produced by the above-mentioned production method 1.

In this production method 2, first, general formula (VI)

Embedded image (Wherein R ³ represents a lower alkyl group) by reacting a lower alkyl ester of propiolic acid and a lower alkyl ester of thioglycolic acid to obtain a compound of the general formula (VII)

Embedded image (Wherein R ² represents a lower alkyl group, and R ³ is the same as described above).

In this reaction, in the presence of a radical type or anionic type catalyst, preferably an anionic type quaternary ammonium salt, substantially 1 mole of the lower alkyl propiolate represented by the general formula (VI) is used. The upper two moles of lower alkyl thioglycolate are preferably reacted. At this time, an appropriate solvent can be used if necessary.

Next, the thus obtained general formula (VI
The tolcarboxylic acid ester represented by I) is reacted with hydrazine monohydrate or the like in the same manner as in Production Method 1 to give a compound of the formula (VIII)

Embedded image 1,5-bis (hydrazinocarbonyl) -3 represented by
-Leads to hydrazinocarbonylmethyl-2,4-dithiapentane.

Finally, the 1,5-bis (hydrazinocarbonyl) -3-hydrazinocarbonylmethyl-2,4
By converting the carbonylhydrazide group of dithiapentane into an isocyanate group in the same manner as in Production Method 1, to obtain the target compound of the formula (Ib)

Embedded image 1,5-diisocyanato-3-isocyanatomethyl-2,4-dithiapentane represented by the following formula:

The polyisocyanate compound represented by the general formula (I) can be produced by a phosgene method in addition to the above-mentioned production method.

Next, the phosgene method will be described by way of an example. First, with respect to 1 mol of dihalogenoacetonitrile represented by the general formula (XI) X ₂ CHCN ... (XI) (wherein X represents a halogen atom), substantially 2 mol of the general formula (XII) MSCN ... (XII) (wherein M represents an alkali metal or ammonium) by reacting a thiocyanate represented by the formula (XIII)

Embedded image After obtaining dithiocyanatoacetonitrile represented by the following formula, hydrogenation is carried out to obtain the formula (XIV)

Embedded image 1,5-diamino-3-aminomethyl-2,
Leads to 4-dithiapentane. Then, by reacting this with phosgene, the desired 1,5-diisocyanato-3-isocyanatomethyl-2,4-dithiapentane represented by the above formula (Ib) is obtained.

The component (A) contains two or more isocyanate groups in one molecule in addition to the polyisocyanate compound represented by the general formula (I) in order to appropriately improve the physical properties and the like of an optical product. One or more compounds may be contained. As these compounds, specifically, o-xylylene diisocyanate, m-xylylene diisocyanate, p-xylylene diisocyanate,
α, α, α ′, α′-tetramethyl-p-xylylene diisocyanate, α, α, α ′, α′-tetramethyl-
m-xylylene diisocyanate, 1,3,5-tris (isocyanatomethyl) benzene, hexamethylene diisocyanate, 1,4-diisocyanatobutane, isophorone diisocyanate, norbornene diisocyanate, bis (4,4'-isocyanatocyclohexyl) Methane, 1,3-bis (isocyanatomethyl) cyclohexane, 1,3,5-tris (isocyanatomethyl) cyclohexane, 1,4-diisocyanatocyclohexane, 1,3,5-triisocyanatocyclohexane, lysine Isocyanate, 2,5-bis (isocyanatomethyl) -1,4-dithiane, 1,3-dithiolane-4,5-diisocyanate, 4,5-bis (isocyanatomethyl) -1,3-dithiolane, Isocyanate methylsul I de, 2-isocyanatoethyl sulfide, bis (isocyanatomethyl thio) methane, 1,2-bis (isocyanatomethyl) ethane, bis (2-isocyanatoethyl thio) methane,
1,2-bis (2-isocyanatoethylthio) ethane, 1,7-diisocyanato-2,4,6-trithiaheptane, 1,5-diisocyanato-2-isocyanatomethyl-3-thiapentane , 1,4-diisocyanato-2-isocyanatomethyl-3-thiabtan and the like. The content of the polyisocyanate compound represented by the general formula (I) in the component (A) is preferably at least 0.1 mol%, particularly preferably at least 5 mol%.

Component (B), which is another raw material of poly (thio) urethane, includes (A) a compound having two or more mercapto groups in one molecule, and (B) two or more compounds in one molecule. A compound having a hydroxyl group and (c) one compound per molecule
A compound containing at least one selected from compounds having one or more hydroxyl groups and one or more mercapto groups is used.

Here, examples of the compound having two or more mercapto groups in one molecule as the component (a) include 2,5.
-Bis (mercaptomethyl) -1,4-dithiane, 2,
5-bis (mercaptomethyl) -1,4-dithiane dimer and multimer (trimer or higher), 1,2,3-trimercaptopropane, tetrakis (7-mercapto-2,5
-Dithiaheptyl) methane, 1,2-ethanedithiol, 1,3-propanedithiol, tetrakismercaptomethylmethane, 2-mercaptoethyl sulfide, pentaerythritol tetrakismercaptopropionate, pentaerythritol tetrakismercaptoacetate, 1,2-benzenedithiol 1,1,3-benzenedithiol, 1,4-benzenedithiol, 1,3,5
-Benzenetrithiol, 1,2-dimercaptomethylbenzene, 1,3-dimercaptomethylbenzene, 1,
4-dimercaptomethylbenzene, 1,3,5-trimercaptomethylbenzene, toluene-3,4-dithiol, tris (3-mercaptopropyl) isocyanurate, 1,3-bis (mercaptomethyl) cyclohexane, 1,4 -Bis (mercaptomethyl) cyclohexane, 2,2-bis (mercaptomethyl) -1,3-propanedithiol, 1,2-bis (2-mercaptoethylthio) -3-mercaptopropane, 4,8-bis (Mercaptomethyl) -3,6,9-trithia-1,11-undecanedithiol.

Examples of the compound having two or more hydroxyl groups in one molecule as the component (b) include ethylene glycol, trimethylolpropane, glycerin, and the like.
Examples include dihydroxybenzene, catechol, 4,4'-dihydroxyphenyl sulfide, 2-hydroxyethyl sulfide, a 5-mol adduct of bisphenol A / propylene oxide, and a 3-mol adduct of glycerin / propylene oxide.

Further, examples of the compound having one or more hydroxyl groups and one or more mercapto groups in one molecule as the component (c) include 2-mercaptoethanol and 2,3
-Dimercaptopropanol, 1,2-dihydroxy-
3-mercaptopropane, 4-mercaptophenol and the like.

As the component (B), the compound containing a mercapto group of the component (A) is preferable, and particularly, the compound represented by the general formula (II):

Embedded image (Where n is an integer of 1 to 20),
5-Bis (mercaptomethyl) -1,4-dithiane and its oligomers are preferred.

In the present invention, the molar ratio of the isocyanate group in the component (A) to the total amount of the mercapto group and the hydroxyl group in the component (B) is NCO group. / (SH group + OH group) is 0.9
It is preferably in the range of 5 to 1.05.

The monomer mixture containing the component (A) and the component (B) has an optical component other than the component (A) and the component (B).
One or more compounds having two or more vinyl groups in one molecule may be contained in order to appropriately improve the properties and the like of the product . In that case, the molar ratio of (isocyanate group + vinyl group) / (mercapto group + hydroxy group) is in the range of 0.95 to 1.5 and (vinyl group) / (isocyanate group). ) Is preferably 0.7 or less, and all the polymerizable functional groups contained in the component (B) are preferably mercapto groups. As these compounds, specifically, 2,
5-bis (2-thia-3-butenyl) -1,4-dithiane, divinylbenzene, ethylene glycol di (meth)
Examples include acrylate, polyethylene glycol di (meth) acrylate, and urethane-modified (meth) acrylate containing at least two or more (meth) acryloxy groups in one molecule. The (meth) acrylate is
Acrylate and methacrylate mean both, and (meth) acryloxy group means both acryloxy group and methacryloxy group.

The optical material of the present invention contains an ultraviolet absorber, a dye or a pigment for improving the light absorption property, an antioxidant or a coloring inhibitor for improving the weather resistance, and a moldability. For improvement, a release agent or the like can be appropriately added as desired.

Here, examples of the ultraviolet absorber include benzotriazoles, benzophenones, and salicylic acids, and examples of the dyes and pigments include anthraquinones and azos.

Examples of the antioxidant and anticolorant include monophenol-based, bisphenol-based, high-molecular-weight phenol-based, sulfur-based, and phosphorus-based agents. Surfactants, acidic phosphate esters, higher fatty acids, and the like.

A catalyst may be appropriately used for improving the polymerization reactivity, and amine compounds, organometallic compounds and the like are effective. Specifically, triethylenediamine, hexamethylenetetramine, N, N-dimethyloctylamine, N, N, N ', N'-tetramethyl-1,6-diaminohexane, 4,4'-trimethylenebis (1 -Methylpiperidine), 1,8-diazabicyclo- (5,4,
0) -7-undecene, dimethyltin dichloride, dimethyltinbis (isooctylthioglycolate), dibutyltin dichloride, dibutyltin dilaurate,
Dibutyltin maleate, dibutyltin maleate polymer, dibutyltin diricinolate, dibutyltin bis (dodecylmercaptide), dibutyltin bis (isooctylthioglycolate), dioctyltin dichloride, dioctyltin maleate, dioctyltin maleate polymer, dioctyltin bis (Butyl maleate), dioctyltin dilaurate, dioctyltin diricinolate, dioctyltin dioleate, dioctyltin di (6-hydroxy) caproate, dioctyltin bis (isooctylthioglycolate), didodecyltin diglycinolate, Copper oleate, copper acetylacetonate, iron acetylacetonate, iron naphthenate, iron lactate, iron citrate, iron gluconate, potassium octanoate,
2-ethylhexyl titanate and the like. The above-mentioned catalysts are effective when used alone or in combination of two or more.

Further, when a vinyl compound is contained in the monomer mixture, it is effective to use an organic peroxide, an azo compound or the like in addition to the above-mentioned catalyst. As an example, the production of the optical product of the present invention using the polyisocyanate compound of the present invention will be described below. The homogeneous mixture of the components (A) and (B) and the additives and catalysts is poured into a known casting polymerization method, that is, a mold in which a glass or metal mold and a resin gasket are combined, and heated. And cure. At this time, in order to facilitate removal of the resin after molding, the mold may be subjected to a release treatment in advance, or a release agent may be mixed into a mixture of the component (A) and the component (B). The polymerization temperature varies depending on the compound used, but is generally -20 to + 150 ° C, and the polymerization time is 0.5 to 72 hours. The optical product of the present invention uses a normal disperse dye, and can be easily dyed in water or an organic solvent.
A carrier may be added or heated. The optical product thus obtained is not particularly limited, but is particularly preferably used as a plastic lens.

[0039]

Next, the present invention will be described in more detail with reference to examples, but the present invention is not limited to these examples.

[0040] The resulting polyisocyanate compound and
The physical properties of the polymer were evaluated according to the methods described below.

(1) ¹ H-NMR spectrum (proton nuclear magnetic resonance spectrum) Measured using an FT-NMR apparatus model EX270 manufactured by JEOL. (2) IR spectrum (infrared absorption spectrum) It was measured using a MAGNA-IR spectrophotometer model 560 manufactured by Nicolet. (3) Refractive index (n _D ) and Abbe number (ν _D ) Measured at 20 ° C. using a KPR-200 precision refractometer manufactured by Calnew. (4) Appearance Observed visually.

(5) Heat resistance The dynamic viscoelasticity was measured at a static tension of 100 g and a frequency of 10 kHz using a dynamic viscoelasticity measuring apparatus manufactured by Toyo Seiki Seisaku-sho, and the elastic modulus obtained by heating at a rate of 2 ° C./min. Was evaluated by the temperature at the descent point of the chart.

[0043] (6) a weatherometer equipped with a weather resistance sunshine carbon arc lamp removed lens was passed lens (optical science products) were set 200 hours, compared to lenses and hue before the test, the following criteria Was used to evaluate the weather resistance. ：: no change Δ: slight yellowing ×: yellowing (7) Solvent resistance A wiping test using acetone was performed, and the solvent resistance was evaluated based on the following criteria. ：: no change ×: swelling or swelling on the surface ：: no distortion is observed ×: distortion is observed

Production Example 1 Production of 1,5-diisocyanato-3-isocyanatomethyl-2,4-dithiapentane 14.7 g (0.15 mol) of ethyl propiolate and 31.8 g (0.3 mol) of methyl thioglycolate ) Was dissolved in 125 ml of benzene, and 0.78 g (0.08 g) of tetrabutylammonium fluoride was used as a catalyst in an ice bath.
After the addition, the mixture was stirred at room temperature for 70 hours. Thereafter, the reaction solution was washed with a dilute aqueous sodium hydroxide solution and water in that order, dried, and benzene was distilled off under reduced pressure. The residue was distilled under reduced pressure to give 1,5-bis (methyloxycarbonyl) -3. -Ethyloxycarbonylmethyl-2,
31.1 g (0.10 mol) of 4-dithiapentane was obtained. (Boiling point: 127 to 129 ° C./0.02 mmHg) This ester compound is dissolved in 30 ml of methanol and added dropwise to a mixed solution of 45.0 g (0.90 mol) of hydrazine monohydrate and 170 ml of methanol at room temperature. Stirred at 70 ° C. for 2 hours. After cooling, the precipitated white crystals were collected by filtration, and recrystallized from methanol-water,
1,5-bis (hydrazinocarbonyl) -3-hydrazinocarbonylmethyl-2,4-dithiapentane 22.0
g (0.075 mol) were obtained.

The hydrazide compound was dissolved in 160 g of a 7.2% by weight aqueous hydrochloric acid solution, and 16.6 g of sodium nitrite (0.24 m
ol) and stirring was continued for 1 hour after completion. The organic phase was removed from the suspension, washed with water, dried (magnesium sulfate), and then heated to complete the transfer reaction. By sufficiently removing toluene as a solvent from the reaction solution, 11.1 g (0.04 g) of a colorless and transparent reaction product was obtained.
5 mol). This reaction product was found to be the target polyisocyanate compound by ¹ H-NMR spectrum and IR spectrum. FIG. 1 shows the ¹ H-NMR spectrum of this novel polyisocyanate compound.
FIG. 2 shows the IR spectrum.

Example 1 0.08 mol of 1,5-diisocyanato-3-isocyanatomethyl-2,4-dithiapentane obtained in Production Example 1 (indicated as DS-1 in Table 1), 2,5 0.12 mol of bis (mercaptomethyl) -1,4-dithiane dimer (designated as DBMD in Table 1) and dibutyltin dilaurate (designated as DBTDL in Table 1) 1.2 × 10 ⁻⁴
mol of the mixture is uniformly stirred, poured into a glass mold for lens molding, and is heated at 50 ° C. for 10 hours, and then at 60 ° C. for 5 hours.
Further, polymerization was carried out by heating at 120 ° C. for 3 hours to obtain a plastic lens. Table 1 shows the physical properties of the obtained plastic lens.
Shown in From Table 1, the polymer obtained using the polyisocyanate compound of Production Example 1 is colorless and transparent, has a very high refractive index (n _D ) of 1.70, and has an Abbe number (ν _D ) of 3
5, high (low dispersion), heat resistance (116 ° C),
It was excellent in weather resistance and solvent resistance, and had no optical distortion.

Examples 2 to 4 As shown in Table 1, the polyisocyanate compound DS-1 [1,5-diisocyanate-3-) obtained in Production Example 1 was used.
Isocyanate methyl-2,4 Jichiapentan] using contains <br/> free monomer composition, the procedure of the actual Example 1 to obtain a plastic lens. Table 1 shows the physical properties of these plastic lenses. From Table 1, the obtained plastic lens is colorless and transparent, and the refractive index (n _D ) is
From 1.67 to 1.69 and very high Abbe's number ([nu _D) also 35-36 high (low dispersion) are those, heat resistance (11
6 to 138 ° C.), excellent in weather resistance and solvent resistance, and without optical distortion.

Comparative Example 1 Pentaerythritol tetrakismercaptopropionate (shown as PETMP in Table 1) 0.06 mol, m
-A mixture of 0.12 mol of xylylene diisocyanate (denoted as XDI in Table 1) and 1.2 × 10 ^-4 mol of dibutyltin dilaurate (denoted as DBTDL in Table 1) is uniformly stirred to form a glass mold for lens molding. Inject 5
10 hours at 0 ° C., then 5 hours at 60 ° C., then 120
Polymerization was carried out at a temperature of 3 ° C. for 3 hours to obtain a plastic lens. Table 1 shows the physical properties of the obtained plastic lens. Table 1
Thus, the plastic lens of Comparative Example 1 was colorless and transparent, no optical distortion was observed, and was excellent in solvent resistance, but had a low refractive index of 1.59 and was inferior in heat resistance (86 ° C.).

Comparative Examples 2-3 Comparative Example 1 was conducted except that the monomer compositions shown in Table 1 were used.
The same operation as described above was performed to obtain a plastic lens. Table 1 shows the physical properties of these plastic lenses. Table 1
Therefore, the refractive index of the plastic lens of Comparative Example 2 was 1.6.
8, which is excellent in heat resistance (128 ° C.) and solvent resistance, is colored yellow, has a low Abbe number (25), is inferior in weather resistance, and has optical distortion. The plastic lens of Comparative Example 3 is colorless and transparent and has a refractive index of 1.
Although it was as high as 68 and no optical distortion was observed, the Abbe number was low (29) and the heat resistance (89 ° C.) and the solvent resistance were poor.

[0050]

[Table 1]

[0051] [Note 1] DS-1: 1,5- diisocyanate 3-isocyanatomethyl-2,4 Jichiapenta down, IMTM: bis (isocyanatomethyl thio) methane, Chti: 1,3,5 Triisocyanatocyclohexane, IPDI: isophorone diisocyanate, DBMD: 2,5-bis (mercaptomethyl) -1,4
Dithiane dimer, BMMD: 2,5-bis (mercaptomethyl) -1,4
-Dithiane, BMMC: 2,5-bis (mercaptomethyl) cyclohexane, TMP: 1,2,3-trimercaptopropane, DBTDL: di-n-butyltin dilaurate, DBTDC: di-n-butyltin dichloride, XDI: m-xylylene diisocyanate, TDI: tolylene diisocyanate, TPDI: 2,4-dithiapentane-1,3-diisocyanate PETMP: pentaerythritol tetrakis (3-mercaptopropionate), XDT: m-xylylene dithiol, PETMA: penta Erythritol tetrakis (2-mercaptoacetate) DMTDC: dimethyltin dichloride

[0052]

The optical product of the present invention contains a sulfur atom in its main chain and is further crosslinked, so that it has a high refractive index and Abbe number, and is excellent in heat resistance, weather resistance, solvent resistance and transparency. It has features such as no optical distortion. Optical product of the present invention
Specific examples of the spectacle lenses, lenses such as camera lenses, prisms, optical fibers, an optical disk, a substrate for a recording medium used in a magnetic disk or the like, the filter over, grayed La <br/> scan, ornaments such as flower bins No.

[Brief description of the drawings]

FIG. 1 is a ¹ H-NMR spectrum of 1,5-diisocyanato-3-isocyanatomethyl-2,4-dithiapentane obtained in Production Example 1.

FIG. 2 is an IR spectrum diagram of 1,5-diisocyanato-3-isocyanatomethyl-2,4-dithiapentane obtained in Production Example 1.

──────────────────────────────────────────────────続 き Continuation of the front page (56) References JP-A-9-71632 (JP, A) JP-A-6-65193 (JP, A) JP-A-9-52931 (JP, A) JP-A-7-716 118390 (JP, A) JP-A-3-236386 (JP, A) JP-A-8-208801 (JP, A) (58) Fields investigated (Int. Cl. ⁷ , DB name) C08G 18/00-18 / 87 G02B 1/00-1/12 G02C 7/02 CA (STN) REGISTRY (STN)

Claims (4)

(57) [Claims] (A) General formula (I) (Wherein, Z represents a direct bond or —CH ₂ — ), a component containing at least a polyisocyanate compound represented by the formula (B) (A), a compound having two or more mercapto groups in one molecule, (B) containing at least one compound selected from among compounds having two or more hydroxyl groups in one molecule and (c) compounds having one or more hydroxyl groups and one or more mercapto groups in one molecule An optical product comprising a poly (thio) urethane obtained by subjecting a monomer mixture containing a component to a polyaddition reaction . 2. The component (A) of the component (B) is represented by the general formula (II): The optical product according to claim 1, wherein the compound is a compound represented by the formula (wherein, n represents an integer of 1 to 20). 3. The optical product according to any one of claims 1 to 2 which is optically transparent. 4. claims 1 is a spectacle lens 3 Neu
2. The optical product according to claim 1 .