PHOSPHORUS-CONTAINING CAPROLACTONE MONOMERS FOR SYNTHESIS OF FLAME RETARDANT POLYCAPROLACTONES

• US 20190248955A1
• Filed: 04/24/2019
• Published: 08/15/2019
• Est. Priority Date: 04/06/2017
• Status: Active Grant

• Current Assignee: International Business Machines Corporation
• Original Assignee: International Business Machines Corporation
• Inventors: Campbell, Eric J., Czaplewski, Sarah K., Kobilka, Brandon M., Wertz, Jason T.
• Granted Patent: US 10,640,608 B2
• Time in Patent Office: Days
• CPC Class Codes: C08G 63/6922 derived from hydroxy carboxylic acids
• CPC Class Codes: C08G 63/78 Preparation processes
• CPC Class Codes: C08G 63/912 derived from hydroxycarboxylic acids

Abstract

A process of forming a flame retardant polycaprolactone includes utilizing a caprolactone molecule to form a hydroxyl-functionalized caprolactone molecule. The process also includes chemically reacting the hydroxyl-functionalized caprolactone molecule with a phosphorus-containing flame retardant molecule to form a flame retardant-functionalized caprolactone monomer. The process further includes polymerizing a mixture that includes at least the flame retardant-functionalized caprolactone monomer to form a flame retardant polycaprolactone.

Claims

1. A process of forming a flame retardant polycaprolactone, the process comprising:

utilizing a caprolactone molecule to form a hydroxyl-functionalized caprolactone molecule;

chemically reacting the hydroxyl-functionalized caprolactone molecule with a phosphorus-containing flame retardant molecule to form a flame retardant-functionalized caprolactone monomer; and

polymerizing a mixture that includes at least the flame retardant-functionalized caprolactone monomer to form a flame retardant polycaprolactone.

2. The process of claim 1, wherein the mixture further includes an unfunctionalized caprolactone monomer, and wherein the flame retardant polycaprolactone includes a flame retardant polycaprolactone copolymer.

3. The process of claim 1, wherein the phosphorus-containing flame retardant molecule includes a cross-linking moiety to cross-link the flame retardant polycaprolactone into a second polymeric material.

4. The process of claim 3, wherein the cross-linking moiety includes an allyl group, an epoxide group, or a furan group.

5. The process of claim 3, wherein the cross-linking moiety includes an allyl group, and wherein the phosphorus-containing flame retardant molecule is formed from allylic alcohol.

6. The process of claim 3, wherein the cross-linking moiety includes an epoxide group, and wherein the phosphorus-containing flame retardant molecule is formed from glycidol.

7. The process of claim 3, wherein the cross-linking moiety includes a furan group, and wherein the phosphorus-containing flame retardant molecule is formed from furfuryl alcohol.

8. The process of claim 3, wherein the cross-linking moiety includes a furan group, and wherein the phosphorus-containing flame retardant molecule is formed from 2-(chloromethyl)furan.

9. A process of forming a flame retardant polycaprolactone, the process comprising:

utilizing a caprolactone molecule to form a hydroxyl-functionalized caprolactone molecule;

chemically reacting the hydroxyl-functionalized caprolactone molecule with a phosphorus-containing flame retardant molecule that includes an allyl group to form a flame retardant-functionalized caprolactone molecule that includes the allyl group;

chemically reacting the allyl group of the flame retardant-functionalized caprolactone molecule with a thiol that includes a cross-linking moiety to form a flame retardant-functionalized caprolactone monomer that includes the cross-linking moiety; and

polymerizing a mixture that includes at least the flame retardant-functionalized caprolactone monomer to form a flame retardant polycaprolactone.

10. The process of claim 9, wherein the cross-linking moiety includes a hydroxyl group, an amine group, a carboxyl group, or an ester group to cross-link the flame retardant polycaprolactone into a second polymeric material.

11. The process of claim 10, further comprising chemically reacting the flame retardant polycaprolactone and the second polymeric material to form a cross-linked flame retardant polymeric material.

12. The process of claim 9, wherein the phosphorus-containing flame retardant molecule includes a phosphate molecule that includes the allyl group and a chloride group to chemically react with a hydroxyl group of the hydroxyl-functionalized caprolactone molecule.

13. The process of claim 9, wherein the phosphorus-containing flame retardant molecule includes a phosphonate molecule that includes the allyl group and a chloride group to chemically react with a hydroxyl group of the hydroxyl-functionalized caprolactone molecule.

14. The process of claim 9, wherein the mixture further includes an unfunctionalized caprolactone monomer, and wherein the flame retardant polycaprolactone includes a flame retardant polycaprolactone copolymer.