IP Library Granted Patent US 10,703,852
Granted Patent B2
US 10,703,852 · App. 15/980,265 · Granted Jul 7, 2020

Isocyanate composition for optical lenses and process for preparing the same

Inventors: Junghwan Shin (Suwon-si, KR); Hyuk Hee Han (Seongnam-si, KR); Jongmin Shim (Hwaseong-si, KR)
Assignee: SKC CO., LTD.
C08G18/7642C07C263/10C08G18/3876G02B1/041
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Quick Facts
Patent No.
US 10,703,852
App. No.
15/980,265
Granted
Jul 7, 2020
Kind
B2
Abstract

An isocyanate composition is prepared from an amine composition, which comprises (a) 99% to less than 100% by weight of m-xylylenediamine; (b) greater than 0% to 0.5% by weight of p-xylylenediamine; and (c) greater than 0% to 0.5% by weight of at least one selected from the group consisting of benzylamine, 4-methylbenzylamine, and 4-cyanobenzylamine. Therefore, the isocyanate composition used in the preparation of a polythiourethane can be controlled to a specific composition in the synthesis thereof, which makes it possible to conveniently produce an optical lens with a high quality.

Claims (30)

1. A process for preparing an isocyanate composition, which comprises:

preparing a first amine composition comprising m-xylylenediamine;

reducing the content of at least one of p-xylylenediamine, benzylamine, 4-methylbenzylamine, and 4-cyanobenzylamine in the first amine composition to obtain a second amine composition; and

synthesizing an isocyanate from the second amine composition to produce the isocyanate composition,

wherein the step of synthesizing the isocyanate is carried out by reacting the second amine composition with phosgene, a halo C 1-10 alkyl chloroformate, or a halo di-C 1-10 alkyl carbonate.

2. The process for preparing an isocyanate composition of claim 1 , wherein the second amine composition comprises:

(a) 99% to less than 100% by weight of m-xylylenediamine;

(b) greater than 0% to 0.5% by weight of p-xylylenediamine; and

(c) greater than 0% to 0.5% by weight of at least one selected from the group consisting of benzylamine, 4-methylbenzylamine, and 4-cyanobenzylamine, based on the total weight of the composition.

3. The process for preparing an isocyanate composition of claim 1 , wherein the second amine composition comprises:

(a) 99.7% to less than 100% by weight of m-xylylenediamine;

(b) greater than 0% to 0.15% by weight of p-xylylenediamine; and

(c) greater than 0% to 0.05% by weight of each of benzylamine, 4-methylbenzylamine, and 4-cyanobenzylamine, based on the total weight of the composition.

4. The process for preparing an isocyanate composition of claim 1 , wherein the step of obtaining the second amine composition is carried out by reducing the contents of all of p-xylylene diamine, benzylamine, 4-methylbenzylamine, and 4-cyanobenzylamine in the first amine composition.

5. The process for preparing an isocyanate composition of claim 1 , wherein the step of obtaining the second amine composition is carried out by a method comprising at least one of:

removing the distilled compounds while the first amine composition is heated to 100 to 185° C. under a reduced pressure; and

removing the precipitated compounds while the first amine composition is cooled to 15 to 18° C.

6. The process for preparing an isocyanate composition of claim 1 , wherein the step of obtaining the second amine composition is carried out by removing the distilled compounds while the first amine composition is heated to 100 to 185° C. under a reduced pressure; and then removing the precipitated compounds while the first amine composition is cooled to 15 to 18° C.

7. The process for preparing an isocyanate composition of claim 1 , wherein the isocyanate composition comprises:

(a′) 99% to less than 100% by weight of m-xylylene diisocyanate;

(b′) greater than 0% to 0.5% by weight of p-xylylene diisocyanate; and

(c′) greater than 0% to 0.5% by weight of at least one selected from the group consisting of benzyl isocyanate, 4-methylbenzyl isocyanate, and 4-cyanobenzyl isocyanate, based on the total weight of the composition.

8. A process for producing an optical lens, which comprises:

preparing a first amine composition comprising m-xylylenediamine;

reducing the content of at least one of p-xylylenediamine, benzylamine, 4-methylbenzylamine, and 4-cyanobenzylamine in the first amine composition to obtain a second amine composition;

synthesizing an isocyanate from the second amine composition to prepare an isocyanate composition; and

mixing the isocyanate composition with a thiol and thermally curing the mixture in a mold,

wherein the step of synthesizing the isocyanate is carried out by reacting the second amine composition with phosgene, a halo C 1-10 alkyl chloroformate, or a halo di-C 1-10 alkyl carbonate.

9. The process for producing an optical lens of claim 8 , wherein the optical lens has a yellowness index (YI) of 1 to 20 and a light transmittance of 85 to 99% at a wavelength of 550 nm.

10. The process for producing an optical lens of claim 9 , wherein the optical lens has an Abbe number of 30 to 45 and a glass transition temperature of 95 to 120° C.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 8, 2024
From: SKC CO., LTD.
To: SK PUCORE CO., LTD.
Reel/Frame 066417/0742 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 7, 2019
From: SHIN, JUNGHWAN; HAN, HYUK HEE; SHIM, JONGMIN
To: SKC CO., LTD.
Reel/Frame 047918/0287 →
Priority Claims (1)
KR 10-2017-0060524 · May 16, 2017 · national
Continuity (1)
Related Publication 20180334531A1 · Nov 22, 2018
Cited By (1)
US 12,503,427