Preparation method of polythiol for optical lenses by using metal sulfide

Patent metadata

Field	Value
Publication number	US-10723697-B2
Application number	US-201815941289-A
Country	US
Kind code	B2
Filing date	Mar 30, 2018
Priority date	Mar 31, 2017
Publication date	Jul 28, 2020
Grant date	Jul 28, 2020

Abstract

Provided is a preparation of a thioether-based polythiol in a high purity using a metal monosulfide for the incorporation of a thioether group, wherein the content of such components as a metal polysulfide present in the metal monosulfide is controlled to a predetermined level or lower. As a result, an optical lens of high quality with a high refractive index can be produced using the polythiol.

First claim

The invention claimed is:

1. A process for preparing a polythiol, which comprises:
(1) preparing a first composition comprising a metal monosulfide;
(2) reducing the content of a metal polysulfide in the first composition to obtain a second composition;
(3) reacting the second composition with a halogenated alcohol to synthesize a polyol having a thioether group; and
(4) reacting the polyol with thiourea, followed by hydrolysis of the resultant to synthesize a polythiol having a thioether group.

2. The process for preparing a polythiol of claim 1 , wherein the content of the metal polysulfide in the second composition is 5% by weight or less.

3. The process for preparing a polythiol of claim 1 , wherein the step (2) further comprises reducing the content of an ammonium salt, a carbonate, a sulfate, and an iodide oxide in the first composition.

4. The process for preparing a polythiol of claim 3 , wherein the total content of the metal polysulfide, the ammonium salt, the carbonate, the sulfate, and the iodide oxide in the second composition is 5% by weight or less.

5. The process for preparing a polythiol of claim 1 , wherein the step (2) is carried out by at least one of (a) washing or recrystallizing the first composition using a difference in solubility, and (b) recrystallizing the first composition using a difference in melting point.

6. The process for preparing a polythiol of claim 1 , wherein the reaction with the halogenated alcohol in the step (3) is carried out by adjusting the amount and the feed rate of the second composition such that the temperature during the reaction is maintained in the range of 0 to 15° C.

7. The process for preparing a polythiol of claim 1 , wherein the reaction with the halogenated alcohol in the above step (3) is carried out after storage of the second composition for one day to twelve months once the second composition has been prepared in the step (2), and the storage is performed under a light-shielding condition at a temperature of 0 to 20° C.

8. The process for preparing a polythiol of claim 1 , wherein the metal polysulfide is represented by the following Formula 2:
(M) n S m   Formula 2

wherein M is Na, K, Mn, Ca, or MgBr; n is 1 or 2 depending on the oxidation number of M; and m is an integer of 2 to 8.

9. The process for preparing a polythiol of claim 1 , wherein the second composition comprises 95% by weight or more of the metal monosulfide represented by the above Formula 1:
(M) n S   Formula 1

wherein M is Na, K, Mn, Ca, or MgBr; and n is 1 or 2 depending on the oxidation number of M.

10. The process for preparing a polythiol of claim 1 , wherein the metal monosulfide is at least one selected from the group consisting of Na 2 S.5H 2 O, Na 2 S.9H 2 O, K 2 S, MnS, CaS, and (MgBr) 2 S.

11. The process for preparing a polythiol of claim 1 , wherein the second composition comprises 95% by weight or more of sodium monosulfide (Na 2 S), and the total content of the sodium polysulfide, an ammonium salt, sodium carbonate, sodium sulfate, and an iodide oxide in the second composition is 5% by weight or less.

12. The process for preparing a polythiol of claim 1 , wherein the polythiol is represented by the following Formula 3:
R 1 —S—R 2   Formula 3

wherein R 1 and R 2 are each independently a linear or branched C1-C20 alkyl group substituted with at least one selected from the group consisting of a thiol group, a hydroxyl group, and an amino group, wherein the total number of the entire thiol groups contained in R 1 and R 2 is 2 to 6; and
R 1 and R 2 may, or may not, each independently contain at least one group selected from the group consisting of —O—, —S—, —C(═O)—O—, —O—C(═O)—O—, —NH—C(═O)—NH—, —NH—C(═S)—O—, —NH—C(═O)—S—, —NH—C(═S)—S—, and —NH—C(═S)—NH— in the alkyl chain.

13. The process for preparing a polythiol of claim 1 , wherein the polythiol has a b* value according to the Lab color space of greater than 0 and 2 or less.

14. A process for preparing an optical lens, which comprises:
(1) preparing a first composition comprising a metal monosulfide;
(2) reducing the content of a metal polysulfide in the first composition to obtain a second composition;
(3) reacting the second composition with a halogenated alcohol to synthesize a polyol having a thioether group;
(4) reacting the polyol with thiourea, followed by hydrolysis of the resultant to synthesize a polythiol having a thioether group; and
(5) mixing the polythiol with an isocyanate and thermally curing the mixture in a mold.

15. The process for preparing an optical lens of claim 14 , wherein the optical lens has a glass transition temperature (Tg) of 80 to 125° C. and a yellow index (YI) of 5 to 15.

Assignees

• Skc Co Ltd

Inventors

• Shin Junghwan
• Hong Seung Mo
• Shim Jongmin
• Han Hyuk Hee
• Myung Jung Hwan
• Seo Hyeon Myeong
• Song Yu Jeong
• JUNG Jooyoung

Classifications

• C07C319/02

  of thiols · CPC title

• G02B1/041

  Lenses · CPC title

• C07C321/14

  of an acyclic saturated carbon skeleton · CPC title

• B29D11/00009 Primary

  Production of simple or compound lenses · CPC title

• C07C319/14 Primary

  of sulfides · CPC title