1,3-bisisocyanatomethylcyclohexane composition and optical resin prepared therefrom

Patent metadata

Field	Value
Publication number	US-12264121-B2
Application number	US-202017772352-A
Country	US
Kind code	B2
Filing date	Jul 7, 2020
Priority date	Nov 29, 2019
Publication date	Apr 1, 2025
Grant date	Apr 1, 2025

Abstract

Disclosed is a 1,3-bisisocyanatomethylcyclohexane composition and an optical resin prepared therefrom. The composition comprises, based on the weight of 1,3-bisisocyanatomethylcyclohexane, a) 65%-95 wt % of trans-1,3-bisisocyanatomethylcyclohexane; b) greater than 0 and less than or equal to 0.5 wt %, preferably 0.02-0.5 wt % of 1,4-bisisocyanatomethylcyclohexane. Preferably, the 1,3-bisisocyanatomethylcyclohexane composition contains greater than 0 and less than or equal to 600 ppm of 1-isocyanatomethyl-3-methylcyclohexane, based on the weight of 1,3-bisisocyanatomethylcyclohexane. The 1,3-bisisocyanatomethylcyclohexane composition is used for preparing an optical resin, which can be applied to produce an optical lens with a better performance in preventing opacification and optical distortion.

First claim

What is claimed is:

1. A 1,3-bis(isocyanatomethyl)cyclohexane composition, comprising: based on a weight of 1,3-bis(isocyanatomethyl)cyclohexane,
a) 65 wt % to 95 wt % of trans-1,3-bis(isocyanatomethyl)cyclohexane; and
b) greater than 0 and less than or equal to 0.5 wt % of 1,4-bis(isocyanatomethyl)cyclohexane;

wherein the 1,3-bis(isocyanatomethyl)cyclohexane comprises cis-1,3-bis(isocyanatomethyl)cyclohexane and trans-1,3-bis(isocyanatomethyl)cyclohexane;
wherein the 1,3-bis(isocyanatomethyl)cyclohexane composition comprises more than 0 and less than or equal to 600 ppm of 1-isocyanatomethyl-3-methylcyclohexane, based on the weight of 1,3-bis(isocyanatomethyl)cyclohexane.

2. The 1,3-bis(isocyanatomethyl)cyclohexane composition according to claim 1 , wherein a preparation method of the composition comprises the following steps: (1) a salt-forming process, mixing a 1,3-cyclohexyldimethylamine raw material with hydrogen chloride to prepare 1,3-cyclohexyldimethylamine hydrochloride; (2) an isocyanate-forming process, subjecting the 1,3-cyclohexyldimethylamine hydrochloride and phosgene to an isocyanate-forming reaction, of which a product includes 1,3-bis(isocyanatomethyl)cyclohexane and 1-isocyanatomethyl-3-methylcyclohexane; and (3) a purification process, performing purification on the product of step (2) to prepare the 1,3-bis(isocyanatomethyl)cyclohexane composition.

3. The 1,3-bis(isocyanatomethyl)cyclohexane composition according to claim 2 , wherein in the 1,3-cyclohexyldimethylamine raw material, trans-1,3-cyclohexyldimethylamine has a content of 50 wt % to 95 wt %, and cis-1,3-cyclohexyldimethylamine has a content of 5 wt % to 50 wt %, based on the weight of 1,3-cyclohexyldimethylamine raw material.

4. The 1,3-bis(isocyanatomethyl)cyclohexane composition according to claim 2 , wherein a preparation method of the 1,3-cyclohexyldimethylamine raw material comprises the following step: subjecting 1,3-cyclohexyldimethylamine (trans-1,3-cyclohexyldimethylamine: cis-1,3-cyclohexyldimethylamine=50:50) to a isomerization reaction for 1 h to 4 h, with a ruthenium/alumina catalyst, a hydrogen absolute pressure of 4 MPa to 6 MPa, and a temperature of 200° C. to 220° C.

5. An optical resin, which is prepared by polymerizing the 1,3-bis(isocyanatomethyl)cyclohexane composition according to claim 1 and a polythiol compound raw material.

6. The optical resin according to claim 5 , wherein the polythiol compound comprises one or more of aliphatic polythiol, aromatic polythiol, polythiol containing a heterocycle, aliphatic polythiol containing a sulfur atom in addition to mercapto, aromatic polythiol containing a sulfur atom in addition to mercapto, and polythiol containing a sulfur atom in addition to a heterocycle and mercapto.

7. The optical resin according to claim 6 , wherein the polythiol compound comprises one or more of 1,2-bis[(2-mercaptoethyl)thio]-3-mercaptopropane, bis(mercaptomethyl)-3,6,9-trithia-1,11-undecanedithiol, pentaerythritol tetrakis(3-mercaptopropionate), 1,1,3,3-tetrakis(mercapto methylthio)propane and 2-mercaptoethanol.

8. A lens, which is prepared from the optical resin according to claim 5 .

9. The 1,3-bis(isocyanatomethyl)cyclohexane composition according to claim 1 , comprising: based on a weight of 1,3-bis(isocyanatomethyl)cyclohexane,
a) 65 wt % to 95 wt % of trans-1,3-bis(isocyanatomethyl)cyclohexane; and
b) 0.02 wt % to 0.5 wt % of 1,4-bis(isocyanatomethyl)cyclohexane.

10. The 1,3-bis(isocyanatomethyl)cyclohexane composition according to claim 1 , wherein the 1,3-bis(isocyanatomethyl)cyclohexane composition comprises 0.1 ppm to 600 ppm of 1-isocyanatomethyl-3-methylcyclohexane, based on the weight of 1,3-bis(isocyanatomethyl)cyclohexane.

11. The 1,3-bis(isocyanatomethyl)cyclohexane composition according to claim 3 , wherein in the 1,3-cyclohexyldimethylamine raw material, trans-1,3-cyclohexyldimethylamine has a content of 65 wt % to 95 wt %, and cis-1,3-cyclohexyldimethylamine has a content of 5 wt % to 35 wt %, based on the weight of 1,3-cyclohexyldimethylamine raw material.

Assignees

• Wanhua Chemical Group Co Ltd

Inventors

• Zhu Fulin
• Li Jianfeng
• Wang Peng
• Li Wenbin
• Chen Jie
• Wang Qiao
• Wu Qian
• Chen Hao
• Shang Yonghua
• Li Yuan

Classifications

• G02B1/041

  Lenses · CPC title

• C08G18/757

  containing at least two isocyanate or isothiocyanate groups linked to the cycloaliphatic ring by means of an aliphatic group · CPC title

• C08G18/3855

  having sulfur · CPC title

• C07B2200/09

  Geometrical isomers · CPC title

• C07C2601/14

  The ring being saturated · CPC title