Pinene-derived diisocyanates

Patent metadata

Field	Value
Publication number	US-11225458-B2
Application number	US-201916674859-A
Country	US
Kind code	B2
Filing date	Nov 5, 2019
Priority date	Oct 6, 2017
Publication date	Jan 18, 2022
Grant date	Jan 18, 2022

Abstract

A pinene-derived diisocyanate compound, a process for forming a pinene-derived polyurethane, and an article of manufacture that includes the polyurethane are disclosed. The process for forming the polyurethane includes forming a pinene-derived diisocyanate compound, and reacting the pinene-derived diisocyanate compound with a polyol in a polymerization compound.

First claim

What is claimed is:

1. A process of forming a polyurethane, comprising:
forming a pinene-derived diisocyanate compound, wherein the forming comprises:
obtaining pinene;
oxidizing the pinene to form a pinene-derived ketone compound;
converting the pinene-derived ketone compound to a diamine compound; and
reacting the diamine compound with phosgene; and

reacting the pinene-derived diisocyanate compound with a polyol in a polymerization reaction.

2. The process of claim 1 , wherein the converting the pinene-derived ketone compound to the diamine compound comprises a reaction between the pinene-derived ketone compound and potassium cyanide.

3. The process of claim 1 , wherein the polymerization reaction is catalyzed by a tertiary amine.

4. The process of claim 1 , wherein the polymerization reaction is catalyzed by a metal based catalyst.

5. The process of claim 1 , further comprising incorporating a blowing agent into the polymerization reaction to form a polyurethane foam.

6. The process of claim 1 , wherein the pinene-derived diisocyanate compound has a formula of:

7. The process of claim 1 , wherein the pinene-derived diisocyanate compound has a formula of:

8. The process of claim 1 , wherein the pinene-derived diisocyanate compound has a formula of:

9. The process of claim 1 , wherein the polyol is selected from the group consisting of polyether polyols, polyester polyols, polycarbonate polyols, graft polyols, polycaprolactone polyols, polybutadiene polyols, polysulfide polyols, and polyols derived from vegetable oils.

10. The process of claim 1 , further comprising adding at least one additive selected from a group consisting of a cross-linker, a chain-extender, an inorganic pigment, an organic pigment, a flame retardant, a surfactant, a filler, a smoke suppressant, and a plasticizer to the polymerization reaction.

11. The process of claim 1 , wherein the polymerization reaction forms a polyurethane foam.

12. The process of claim 1 , wherein the obtaining the pinene comprises:
obtaining a resin from a plant source; and
isolating the pinene from the resin.

Assignees

• IBM

Inventors

• Kobilka Brandon M
• Kuczynski Joseph
• Porter Jacob T
• Wertz Jason T

Classifications

• C08G18/758 Primary

  containing two or more cycloaliphatic rings · CPC title

• C07C2601/14

  The ring being saturated · 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

• C07C253/10

  to compounds containing carbon-to-carbon double bonds · CPC title

• C07C209/62

  by cleaving carbon-to-nitrogen, sulfur-to-nitrogen, or phosphorus-to-nitrogen bonds, e.g. hydrolysis of amides, N-dealkylation of amines or quaternary ammonium compounds (C07C209/24 takes precedence) · CPC title