Terminally-functionalized cashew nut shell liquid derivatives

Patent metadata

Field	Value
Publication number	US-11274177-B2
Application number	US-201916411422-A
Country	US
Kind code	B2
Filing date	May 14, 2019
Priority date	May 14, 2019
Publication date	Mar 15, 2022
Grant date	Mar 15, 2022

Abstract

A terminally-functionalized derivative of a cashew nut shell liquid (CNSL) compound, a method to form a polymer, and an article of manufacture comprising a polymer derived from the terminally-functionalized CNSL derivative. The terminally-functionalized CNSL derivative has two, three, four, or five reactive functional groups. The polymer is prepared by obtaining CNSL compounds, reacting the CNSL compounds to form the terminally-functionalized CNSL derivative, and polymerizing the terminally-functionalized CNSL derivative.

First claim

What is claimed is:

1. A compound having the structure:

wherein R, R′, R″, Q, and Q′ are hydroxyl groups.

2. A method, comprising:
obtaining a cashew nutshell liquid (CNSL) compound;
converting sidechain alkene moieties on the CNSL compound to alkyne moieties to form an alkyne CNSL derivative;
reacting the alkyne CNSL derivative with a base to form a terminal alkyne CNSL derivative;
hydroxylating the terminal alkyne CNSL derivative to form a terminal polyol CNSL derivative; and
polymerizing the terminal polyol CNSL derivative.

3. The method of claim 2 , wherein the polymerizing comprises forming a polyurethane.

4. The method of claim 3 , wherein the forming the polyurethane comprises reacting the terminal polyol CNSL derivative with an isocyanate.

5. The method of claim 4 , wherein the isocyanate is selected from the group consisting of toluene diisocyanate, pentamethylene diisocyanate (PDI), methylene dicyclohexyl diisocyanate (MDI), hydrogenated MDI, isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), HDI trimer, HDI biuret, HDI uretdione, and IPDI trimer.

6. The method of claim 2 , wherein the polymerizing comprises reacting the terminal polyol CNSL derivative with a diisocyanate.

7. The method of claim 2 , wherein the polymerizing comprises adding a blowing agent.

8. The method of claim 2 , wherein the polymerizing comprises forming a mixture, the mixture comprising:
the terminal polyol CNSL derivative; and
at least one monomer from a non-CNSL source.

9. The method of claim 8 , wherein the at least one monomer is a petrochemical-derived polyol.

10. An article of manufacture comprising a polymer, the polymer comprising:
a number (n) of repeat units derived from a terminally-functionalized cashew nutshell liquid (CNSL) derivative having the structure:

wherein R, R′, R″, Q, and Q′ are hydroxyl groups.

11. The article of manufacture of claim 10 , wherein the polymer is a polyurethane.

12. The article of manufacture of claim 10 , wherein the polymer is a foam.

13. The article of manufacture of claim 10 , wherein the polymer is a polyester.

14. The article of manufacture of claim 10 , wherein at least 5% by weight of the polymer is derived from the CNSL derivative.

Assignees

• IBM

Inventors

• Kobilka Brandon M
• Porter Jacob
• Wertz Jason T
• King Scott B

Classifications

• C08G63/133

  Hydroxy compounds containing aromatic rings · CPC title

• C08G18/3215 Primary

  containing aromatic groups or benzoquinone groups · CPC title

• C07C37/00

  Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring · CPC title

• C08G2110/0008

  flexible · CPC title

• C07C39/11

  Alkylated hydroxy benzenes containing also acyclically bound hydroxy groups, e.g. saligenol · CPC title