Method for producing polythiol compound, method for producing curable composition, and method for producing cured product

Patent metadata

Field	Value
Publication number	US-10975026-B2
Application number	US-201816171476-A
Country	US
Kind code	B2
Filing date	Oct 26, 2018
Priority date	Jun 30, 2016
Publication date	Apr 13, 2021
Grant date	Apr 13, 2021

Abstract

The method for producing a polythiol compound includes reacting 2-mercaptoethanol having a water content of 3000 ppm or less on a mass basis, with epihalohydrin to obtain a halide represented by the formula (1), wherein X represents a halogen atom; and obtaining at least one polythiol compound selected from the group consisting of a polythiol compound represented by the formula (4), a polythiol compound represented by the formula (5), a polythiol compound represented by the formula (6), and a polythiol compound represented by the formula (7).

First claim

What is claimed is:

1. A method for producing a polythiol compound, the method comprising:
reacting 2-mercaptoethanol having a water content of 3000 ppm or less on a mass basis, with epihalohydrin to obtain a halide represented by the formula (1),

wherein X represents a halogen atom;
reacting the halide represented by the formula (1) with an alkali metal compound selected from the group consisting of an alkali metal sulfide and an alkali metal hydroxide to obtain a polyol compound selected from the group consisting of a polyol compound represented by the formula (2) and a polyol compound represented by the formula (3),

reacting the polyol compound with thiourea in the presence of an acid to obtain an isothiuronium salt;
hydrolyzing the isothiuronium salt in the presence of a base to obtain a polythiol salt; and
converting the polythiol salt into a polythiol by an acid to obtain at least one polythiol compound selected from the group consisting of a polythiol compound represented by the formula (4), a polythiol compound represented by the formula (5), a polythiol compound represented by the formula (6), and a polythiol compound represented by the formula (7),

2. The method for producing a polythiol compound according to claim 1 ,
wherein the alkali metal compound is an alkali metal compound selected from the group consisting of sodium sulfide and sodium hydroxide.

3. The method for producing a polythiol compound according to claim 1 ,
wherein the polythiol salt is a salt selected from the group consisting of a polythiol alkali metal salt and a polythiol ammonium salt.

4. A method for producing a curable composition, the method comprising:
producing a polythiol compound according to the production method according to claim 1 ; and
mixing the produced polythiol compound with a polyiso(thio)cyanate compound to prepare the curable composition.

5. A method for producing a cured product, the method comprising:
producing a curable composition according to the production method according to claim 4 ; and
curing the produced curable composition to obtain the cured product.

6. The method for producing a cured product according to claim 5 , wherein the curing is carried out by subjecting the curable composition to cast polymerization.

7. The method for producing a cured product according to claim 5 , wherein the cured product is a spectacle lens base material.

8. A method for producing a curable composition, the method comprising:
producing a polythiol compound according to the production method according to claim 2 ; and
mixing the produced polythiol compound with a polyiso(thio)cyanate compound to prepare the curable composition.

9. A method for producing a curable composition, the method comprising:
producing a polythiol compound according to the production method according to claim 3 ; and
mixing the produced polythiol compound with a polyiso(thio)cyanate compound to prepare the curable composition.

10. A method for producing a cured product, the method comprising:
producing a curable composition according to the production method according to claim 8 ; and
curing the produced curable composition to obtain the cured product.

11. A method for producing a cured product, the method comprising:
producing a curable composition according to the production method according to claim 9 ; and
curing the produced curable composition to obtain the cured product.

12. The method for producing a cured product according to claim 10 ,
wherein the curing is carried out by subjecting the curable composition to cast polymerization.

13. The method for producing a cured product according to claim 11 ,
wherein the curing is carried out by subjecting the curable composition to cast polymerization.

14. The method for producing a cured product according to claim 10 ,
wherein the cured product is a spectacle lens base material.

15. The method for producing a cured product according to claim 11 ,
wherein the cured product is a spectacle lens base material.

16. The method for producing a polythiol compound according to claim 1 ,
wherein the reacting of the 2-mercaptoethanol having a water content of 3000 ppm or less on a mass basis with the epihalohydrin is performed in the absence of a solvent or in the presence of a solvent consisting of an alcohol.

Assignees

• Hoya Lens Thailand Ltd

Inventors

• Kageyama Yukio
• Kousaka Masahisa
• Yamamoto Akinori

Classifications

• C07C319/14 Primary

  of sulfides · CPC title

• C07C319/20

  by reactions not involving the formation of sulfide groups · CPC title

• C07C335/32

  having sulfur atoms of isothiourea groups bound to acyclic carbon atoms · CPC title

• C08G18/7642

  containing at least two isocyanate or isothiocyanate groups linked to the aromatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate groups, e.g. xylylene diisocyanate or homologues substituted on the aromatic ring · CPC title

• C08G18/246

  containing also tin-carbon bonds · CPC title