Flame retardant materials derived from furan dicarboxylic methyl ester

Patent metadata

Field	Value
Publication number	US-9822208-B1
Application number	US-201715397406-A
Country	US
Kind code	B1
Filing date	Jan 3, 2017
Priority date	Jan 3, 2017
Publication date	Nov 21, 2017
Grant date	Nov 21, 2017

Abstract

A process of forming a flame retardant material from furan dicarboxylic methyl ester (FDME) includes converting an FDME molecule to a 2,5-furan dicarbonyl dichloride (FDCC) molecule and chemically reacting the FDCC molecule with a phosphorus-containing material to form an FDME-based flame retardant material that includes a phosphorus-based flame retardant moiety.

First claim

What is claimed is:

1. A process of forming a flame retardant material from furan dicarboxylic methyl ester (FDME), the process comprising:
converting a furan dicarboxylic methyl ester (FDME) molecule to a 2,5-furan dicarbonyl dichloride (FDCC) molecule; and
chemically reacting the FDCC molecule with a phosphorus-containing material to form an FDME-derived flame retardant material that includes a phosphorus-based flame retardant moiety.

2. The process of claim 1 , further comprising forming the FDME molecule from renewable resource-derived fructose.

3. The process of claim 1 , wherein the FDME-derived flame retardant material includes an FDME-derived flame retardant molecule that includes two phosphorus-based flame retardant moieties.

4. The process of claim 1 , further comprising chemically reacting the FDME-derived flame retardant material with an alcohol-functionalized reactive group to form a second FDME-derived flame retardant material, the second FDME-derived flame retardant material including the phosphorus-based flame retardant moiety and a cross-linkable functional group.

5. The process of claim 4 , wherein the alcohol-functionalized reactive group includes allyl alcohol, and wherein the cross-linkable functional group includes an allyl group.

6. The process of claim 5 , wherein the second FDME-derived flame retardant material includes an FDME-derived flame retardant molecule that includes the phosphorus-based flame retardant moiety and the allyl group.

7. The process of claim 4 , wherein the second FDME-derived flame retardant material includes an FDME-derived flame retardant oligomer having a terminal cross-linkable functional group and a single phosphorus-based flame retardant moiety per oligomeric repeat unit.

8. The process of claim 7 , wherein the terminal cross-linkable functional group includes an allyl group.

9. The process of claim 4 , wherein the second FDME-derived flame retardant material includes an FDME-derived flame retardant polymer having two terminal phosphorus-based flame retardant moieties and two phosphorus-based flame retardant moieties per polymeric repeat unit.

10. The process of claim 4 , wherein the second FDME-derived flame retardant material includes an FDME-derived flame retardant polymer having two terminal cross-linkable functional groups and two phosphorus-based flame retardant moieties per polymeric repeat unit.

11. The process of claim 10 , wherein the two terminal cross-linkable functional groups include allyl groups.

12. A furan dicarboxylic methyl ester (FDME)-derived flame retardant material formed by a process comprising:
converting a furan dicarboxylic methyl ester (FDME) molecule to a 2,5-furan dicarbonyl dichloride (FDCC) molecule; and
chemically reacting the FDCC molecule with a phosphorus-containing material to form an FDME-derived flame retardant material that includes a phosphorus-based flame retardant moiety.

13. The FDME-derived flame retardant material of claim 12 , the process further comprising forming the FDME molecule from renewable resource-derived fructose.

14. The FDME-derived flame retardant material of claim 12 , wherein the FDME-derived flame retardant material includes an FDME-derived flame retardant molecule that includes two phosphorus-based flame retardant moieties.

15. A furan dicarboxylic methyl ester (FDME)-derived flame retardant material formed by a process comprising:
converting a furan dicarboxylic methyl ester (FDME) molecule to a 2,5-furan dicarbonyl dichloride (FDCC) molecule;
chemically reacting the FDCC molecule with a phosphorus-containing material to form a first FDME-derived flame retardant material that includes a phosphorus-based flame retardant moiety; and
chemically reacting the first FDME-derived flame retardant material with an alcohol-functionalized reactive group to form a second FDME-derived flame retardant material, the second FDME-derived flame retardant material including the phosphorus-based flame retardant moiety and a cross-linkable functional group.

16. The FDME-derived flame retardant material of claim 15 , wherein the alcohol-functionalized reactive group includes allyl alcohol, and wherein the cross-linkable functional group includes an allyl group.

17. The FDME-derived flame retardant material of claim 16 , wherein the first FDME-derived flame retardant material includes a molecule having a chlorocarbonyl group, and wherein the chlorocarbonyl group is converted to an allyl group to form the second FDME-derived flame retardant material.

18. The FDME-derived flame retardant material of claim 15 , wherein the first FDME-derived flame retardant material includes an oligomer having a terminal chloride group, and wherein the terminal chloride group is converted to a terminal allyl group to form the second FDME-derived flame retardant material.

19. The FDME-derived flame retardant material of claim 16 , wherein the first FDME-derived flame retardant material includes a polymer having two terminal chlorocarbonyl groups, and wherein the two terminal chlorocarbonyl groups are converted to two terminal allyl groups to form the second FDME-derived flame retardant material.

20. The FDME-derived flame retardant material of claim 19 , wherein the second FDME-derived flame retardant material has two phosphorus-based flame retardant moieties per polymeric repeat unit.

Assignees

• IBM

Inventors

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

Classifications

• C07F9/65515 Primary

  the oxygen atom being part of a five-membered ring · CPC title

• C08L45/00

  Compositions of homopolymers or copolymers of compounds having no unsaturated aliphatic radicals in side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic or in a heterocyclic ring system; Compositions of derivatives of such polymers (of cyclic anhydrides or imides C08L35/00; of cyclic esters of polyfunctional acids C08L31/00) · CPC title

• C08F234/02 Primary

  in a ring containing oxygen (coumarone-indene polymers C08F244/00) · CPC title

• C08K5/5373

  containing heterocyclic rings not representing cyclic esters of phosphonic acids · CPC title

• C08L2201/02

  Flame or fire retardant/resistant · CPC title