Diamine composition, and method of preparing diisocyanate composition

Patent metadata

Field	Value
Publication number	US-11760719-B2
Application number	US-202017111779-A
Country	US
Kind code	B2
Filing date	Dec 4, 2020
Priority date	Dec 6, 2019
Publication date	Sep 19, 2023
Grant date	Sep 19, 2023

Abstract

A diamine composition comprising a benzylmonoamine having a methyl group in an amount of 10 ppm to 2,000 ppm in the composition and use thereof for the preparation of a diisocyanate composition and an optical material. A process for preparing a diisocyanate composition wherein the b* value according to the CIE color coordinate of the diamine composition is adjusted to a specific range, whereby the yield and purity of the diisocyanate composition and the optical characteristics of the final optical lens are enhanced. Use of the process for the diisocyanate composition for preparing a plastic optical lens of high quality.

First claim

The invention claimed is:

1. A process for preparing a diisocyanate composition, which comprises:
reacting a diamine composition with an aqueous hydrochloric acid solution to obtain a diamine hydrochloride composition; and
obtaining a diisocyanate composition by reacting the diamine hydrochloride composition with triphosgene,
wherein the diamine composition comprises a diamine; and a benzylmonoamine having a methyl group in an amount of 10 ppm to 2,000 ppm based on the total amount of the diamine composition, and
wherein after the reaction of the diamine composition and the aqueous hydrochloric acid solution, a first organic solvent is further added to obtain the diamine hydrochloride composition in a solid phase,
wherein the reaction of the diamine hydrochloride composition with triphosgene is carried out in a second organic solvent,
wherein the second organic solvent is introduced to the reaction in an amount of 3 to 5 times of the weight of the diamine hydrochloride composition,
wherein the first organic solvent is at least one selected from the group consisting of diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, methanol, ethanol, dimethyl sulfoxide, dimethylformamide, acetonitrile, acetone, trichloroethylene, tetrachloroethane, trichloroethanol, n-butanol, isobutanol, methyl ethyl ketone, methyl butyl ketone, isopropanol, hexane, chloroform, and methyl acetate,
wherein the second organic solvent is at least one selected from the group consisting of benzene, toluene, ethylbenzene, chlorobenzene, monochlorobenzene, 1,2-dichlorobenzene, dichloromethane, 1-chloro-n-butane, 1-chloro-n-pentane, 1-chloro-n-hexane, chloroform, carbon tetrachloride, n-pentane, n-hexane, n-heptane, n-octane, cyclohexane, cyclopentane, cyclooctane, and methylcyclohexane.

2. The process for preparing a diisocyanate composition of claim 1 , wherein the diamine hydrochloride composition comprises a benzylmonoamine hydrochloride having a methyl group,
the benzylmonoamine hydrochloride having a methyl group is reacted with triphosgene to produce a benzyl isocyanate having a methyl group,
the benzyl isocyanate having a methyl group is contained in the diisocyanate composition in an amount of 5 ppm to 200 ppm based on the amount of the diisocyanate composition, and
the ratio of the content of the benzyl isocyanate having a methyl group to the content of the benzylmonoamine having a methyl group which remains unconverted in the diisocyanate composition is 0.05 to 0.9.

3. The process for preparing a diisocyanate composition of claim 2 , which further comprises distilling the reaction resultant obtained by reacting the diamine hydrochloride composition and triphosgene, and the distillation comprises a first distillation at 40° C. to 60° C. for 2 hours to 8 hours and a second distillation at 100° C. to 120° C. for 2 to 10 hours.

4. The process for preparing a diisocyanate composition of claim 1 , wherein the diamine hydrochloride composition and triphosgene are introduced to the reaction at an equivalent ratio of 1:1 to 5, and the reaction of the diamine hydrochloride composition and triphosgene is carried out at a temperature of 110° C. to 160° C.

Assignees

• Skc Co Ltd
• Woori Fine Chem Co Ltd

Inventors

• Pai Jaeyoung
• Kim Jeongmoo
• Han Hyuk Hee
• Myung Jung Hwan
• JUNG Jooyoung
• Kyun Myung-Ok

Classifications

• C07C263/10 Primary

  by reaction of amines with carbonyl halides, e.g. with phosgene · CPC title

• C07C263/20 Primary

  Separation; Purification · CPC title

• C07C209/74

  by halogenation, hydrohalogenation, dehalogenation, or dehydrohalogenation · CPC title

• C08G18/753

  containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group · CPC title

• C08G18/3876

  containing mercapto groups · CPC title