Method of preparing diisocyanate composition and optical lens

Patent metadata

Field	Value
Publication number	US-11518737-B2
Application number	US-202017109893-A
Country	US
Kind code	B2
Filing date	Dec 2, 2020
Priority date	Dec 5, 2019
Publication date	Dec 6, 2022
Grant date	Dec 6, 2022

Abstract

In the embodiments, an aqueous hydrochloric acid solution and an organic solvent instead of hydrogen chloride gas and solid triphosgene instead of phosgene gas may be used in the process of preparing a diisocyanate from a diamine through a diamine hydrochloride. In addition, the embodiments provide processes for preparing a diisocyanate composition and an optical lens, which are excellent in yield and quality with mitigated environmental problems by controlling the total content of metals, cations, or anions in a diamine hydrochloride composition.

First claim

The invention claimed is:

1. A process for preparing a diisocyanate composition, which comprises:
obtaining a diisocyanate composition using a diamine hydrochloride composition,
wherein the diamine hydrochloride composition is obtained by a process comprising reacting a diamine with an aqueous hydrochloric acid solution;
adding a first organic solvent to the reaction resultant of the diamine and the aqueous hydrochloric acid solution; and
washing the diamine hydrochloride composition with a solvent having a polarity index of 3.9 to 5.7,
dissolving the diamine hydrochloride composition in a solvent having a polarity index of 6.2 to 9.8 and recrystallizing the diamine hydrochloride composition,
wherein, in the recrystallization, an amphiphilic organic solvent and an aqueous hydrochloric acid solution having a concentration of 20% to 45% by weight are added to recrystallize 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 solvent having the polarity index of 3.9 to 5.7 is at least one selected from the group consisting of tetrahydrofuran (THF), methyl acetate, methyl ethyl ketone, and acetone, and
wherein the total content of metals in the diamine hydrochloride composition is 100 ppm or less.

2. The process for preparing a diisocyanate composition of claim 1 , wherein the first organic solvent is introduced to the reaction in an amount of 1.3 to 1.5 times the weight of the aqueous hydrochloric acid solution, and
the diamine and the aqueous hydrochloric acid solution are introduced to the reaction at an equivalent ratio of 1:2 to 5.

3. The process for preparing a diisocyanate composition of claim 1 , wherein the diamine is xylylenediamine, the diisocyanate composition comprises xylylene diisocyanate, and the total content of metals in the diisocyanate composition is 5 ppm or less.

4. The process for preparing a diisocyanate composition of claim 1 , wherein the diisocyanate composition is obtained by reacting the diamine hydrochloride composition and triphosgene, and
the diisocyanate composition is obtained as a result of subjecting the resultant of the reaction of the diamine hydrochloride composition and the triphosgene to first distillation at 40° C. to 60° C. for 2 to 8 hours and second distillation at 100° C. to 120° C. for 2 to 10 hours.

5. 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;
washing the diamine hydrochloride composition with a solvent having a polarity index of 3.9 to 5.7 before it is reacted with triphosgene;
measuring the total content of cations in the diamine hydrochloride composition before it is reacted with triphosgene; and
reacting the diamine hydrochloride composition with triphosgene to obtain a diisocyanate composition;
wherein the solvent having the polarity index of 3.9 to 5.7 is at least one selected from the group consisting of tetrahydrofuran (THF), methyl acetate, methyl ethyl ketone, and acetone, and
wherein the total content of cations in the diamine hydrochloride composition is adjusted to 100 ppm or less.

6. The process for preparing a diisocyanate composition of claim 5 , wherein the cations in the diamine hydrochloride composition comprises an ion of at least one metal selected from the group consisting of Fe, Na, Ca, Mg, Cr, Mn, Ni, Cu, and Zn.

7. 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;
washing the diamine hydrochloride composition with a solvent having a polarity index of 3.9 to 5.7 before it is reacted with triphosgene;
measuring the total content of anions in the diamine hydrochloride composition before it is reacted with triphosgene; and
reacting the diamine hydrochloride composition with triphosgene to obtain a diisocyanate composition;
wherein the solvent having a polarity index of 3.9 to 5.7 is at least one selected from the group consisting of tetrahydrofuran (THF), methyl acetate, methyl ethyl ketone, and acetone, and
wherein the total content of anions in the diamine hydrochloride composition is adjusted to 100 ppm or less.

8. The process for preparing a diisocyanate composition of claim 5 , which further comprises dissolving the diamine hydrochloride composition in a solvent having a polarity index of 6.2 to 9.8 and recrystallizing it before it is reacted with triphosgene,
wherein, in the recrystallization, an amphiphilic organic solvent and an aqueous hydrochloric acid solution having a concentration of 20% to 45% by weight are added to recrystallize the diamine hydrochloride composition.

9. The process for preparing a diisocyanate composition of claim 7 , wherein the anions in the diamine hydrochloride composition are at least one selected from the group consisting of Cl − , NO 3 − , SO 4 2− , F − , Br − , NO 2 − , and PO 4 − .

10. The process for preparing a diisocyanate composition of claim 5 , wherein the step of obtaining the diisocyanate composition sequentially comprises:
(2-1) mixing the diamine hydrochloride composition with a second organic solvent to obtain a first solution;
(2-2) mixing triphosgene with the second organic solvent to obtain a second solution; and
(2-3) introducing the second solution to the first solution at 115° C. to 160° C. and stirring them.

11. The process for preparing a diisocyanate composition of claim 5 , wherein the diisocyanate composition is obtained by distillation after the reaction of the diamine hydrochloride composition and triphosgene,
the distillation comprises distillation of a diisocyanate at a temperature of 100° C. to 130° C. and a pressure of 2.0 torr or less,
the yield of the distillation of a diisocyanate is 90% or more,
the diisocyanate composition comprises 99.0% by weight or more of the diisocyanate before the distillation of a diisocyanate, and
the diisocyanate composition, after the distillation of a diisocyanate, comprises the diisocyanate in an amount of 99.9% by weight or more.

12. A process for preparing an optical lens, which comprises:
mixing a diisocyanate composition prepared by the process of claim 1 with a thiol or an episulfide and polymerizing and curing the resultant in a mold.

13. The process for preparing an optical lens of claim 12 , wherein the optical lens has a light transmittance of 90% or more and a yellow index (Y.I.) of 22 or less.

14. The process for preparing a diisocyanate composition of claim 7 , which further comprises dissolving the diamine hydrochloride composition in a solvent having a polarity index of 6.2 to 9.8 and recrystallizing it before it is reacted with triphosgene,
wherein, in the recrystallization, an amphiphilic organic solvent and an aqueous hydrochloric acid solution having a concentration of 20% to 45% by weight are added to recrystallize the diamine hydrochloride composition.

15. The process for preparing a diisocyanate composition of claim 7 , wherein the step of obtaining the diisocyanate composition sequentially comprises:
(2-1) mixing the diamine hydrochloride composition with a second organic solvent to obtain a first solu

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

• C07C2601/14

  The ring being saturated · CPC title

• C08G18/73

  acyclic · CPC title

• Y02P20/582

  Recycling of unreacted starting or intermediate materials · CPC title

• G02B1/041

  Lenses · CPC title

• C08G18/755

  and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate · CPC title