Phosphorus-containing caprolactone monomers for synthesis of flame retardant polycaprolactones

• US 10,336,861 B2
• Filed: 04/06/2017
• Issued: 07/02/2019
• 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.
• Primary Examiner(s): Choi, Ling Siu
• Assistant Examiner(s): Grinsted, Ronald
• Application Number:
  US15/480,785
• Publication Number:
  US 20180291143A1
• Time in Patent Office: 817 Days
• Field of Search: 526 75
• 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 flame retardant polycaprolactone formed according to a 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, wherein the phosphorus-containing flame retardant molecule includes an allyl group, an epoxide group, or a furan group; and

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

2. The flame retardant polycaprolactone 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 flame retardant polycaprolactone of claim 1, wherein a cross-linking moiety includes an allyl group, and wherein the phosphorus-containing flame retardant molecule is formed from allylic alcohol or allyl chloride.

4. The flame retardant polycaprolactone of claim 1, wherein a cross-linking moiety includes an epoxide group, and wherein the phosphorus-containing flame retardant molecule is formed from glycidol or epichlorohydrin.

5. The flame retardant polycaprolactone of claim 1, wherein a cross-linking moiety includes a furan group, and wherein the phosphorus-containing flame retardant molecule is formed from furfuryl alcohol.

6. The flame retardant polycaprolactone of claim 1, wherein a cross-linking moiety includes a furan group, and wherein the phosphorus-containing flame retardant molecule is formed from 2-(chloromethyl)furan.