Flame-retardant polydiketoenamines

Patent metadata

Field	Value
Publication number	US-11912830-B2
Application number	US-202017126239-A
Country	US
Kind code	B2
Filing date	Dec 18, 2020
Priority date	Dec 18, 2020
Publication date	Feb 27, 2024
Grant date	Feb 27, 2024

Abstract

A composition, method, and article of manufacture are disclosed. The composition is formed by polymerizing monomers, and includes at least one flame-retardant bis(triketone) monomer and at least one amine monomer. The method includes obtaining at least one flame-retardant bis(triketone) monomer, obtaining at least one amine monomer, and polymerizing the monomers to form a flame-retardant polydiketoenamine. The article of manufacture includes a polymer formed by polymerizing at least one flame-retardant bis(triketone) monomer and at least one amine monomer.

First claim

What is claimed is:

1. A composition formed by polymerizing monomers, the monomers comprising:
at least one flame-retardant bis(triketone) monomer comprising a phosphoryl group; and
at least one amine monomer.

2. The composition of claim 1 , wherein the at least one amine monomer is selected from the group consisting of tris(2-aminoethyl)amine, poly(propylene glycol) bis(2-aminopropyl ether), poly(ethylene glycol) bis(2-aminopropyl ether), poly(ethylene glycol) bis(amine), dipropylenetriamine, diethylenetriamine, diaminooctane, 4,4′-oxydianiline, and combinations thereof.

3. The composition of claim 1 , wherein the at least one flame-retardant bis(triketone) monomer is an organophosphorus compound selected from the group consisting of organophosphates, organophosphonates, organophosphinates, organophosphites, and organophosphonites.

4. The composition of claim 1 , wherein the monomers further comprise at least one non-flame-retardant bis(triketone) monomer.

5. The composition of claim 1 , wherein the at least one flame-retardant bis(triketone) monomer is derived from a dicarboxyl flame retardant.

6. The composition of claim 1 , wherein the at least one amine monomer has at least two primary amine groups.

7. A method, comprising:
obtaining at least one flame-retardant bis(triketone) monomer comprising a phosphoryl group;
obtaining at least one amine monomer; and
polymerizing the at least one flame-retardant bis(triketone) monomer and the at least one amine monomer to form a flame-retardant polydiketoenamine.

8. The method of claim 7 , wherein the polymerizing is carried out in a ball mill.

9. The method of claim 7 , wherein the at least one amine monomer is selected from the group consisting of tris(2-aminoethyl)amine, poly(propylene glycol) bis(2-aminopropyl ether), poly(ethylene glycol) bis(2-aminopropyl ether), poly(ethylene glycol) bis(amine), dipropylenetriamine, diethylenetriamine, diaminooctane, 4,4′-oxydianiline, and combinations thereof.

10. The method of claim 7 , wherein the at least one flame-retardant bis(triketone) monomer is an organophosphorus compound selected from the group consisting of organophosphates, organophosphonates, organophosphinates, organophosphites, and organophosphonites.

11. The method of claim 7 , wherein the obtaining the at least one flame-retardant bis(triketone) monomer comprises reacting a dicarboxyl flame retardant with a diketone compound.

12. The method of claim 11 , wherein the diketone compound is a 1,3-diketone.

13. The method of claim 11 , wherein the dicarboxyl flame retardant has the following structure:

wherein:
each Y is a substituent comprising a carboxyl group;
R is an organic substituent; and
n is an integer greater than or equal to 1.

14. The method of claim 7 , further comprising:
obtaining at least one non-flame-retardant bis(triketone) monomer; and
including the at least one non-flame-retardant bis(triketone) monomer in the polymerizing.

15. The method of claim 7 , wherein the polymerizing forms a flame-retardant polydiketoenamine (PDK).

16. The method of claim 7 , wherein the flame-retardant bis(triketone) monomer has the following structure:

17. An article of manufacture, comprising:
a flame-retardant polymer formed by polymerizing monomers, the monomers comprising:
at least one flame-retardant bis(triketone) monomer comprising a phosphoryl group; and
at least one amine monomer.

18. The article of manufacture of claim 17 , wherein the at least one flame-retardant bis(triketone) monomer is an organophosphorus compound selected from the group consisting of organophosphates, organophosphonates, organophosphinates, organophosphites, and organophosphonites.

19. The article of manufacture of claim 17 , wherein the at least one amine monomer has at least two primary amine groups.

20. The article of manufacture of claim 17 , wherein the at least one flame-retardant bis(triketone) monomer is derived from a dicarboxyl flame retardant.

Assignees

• IBM

Inventors

• Kobilka Brandon M
• Wertz Jason T
• Czaplewski-Campbell Sarah K
• Campbell Eric J

Classifications

• C08G79/04 Primary

  Phosphorus linked to oxygen or to oxygen and carbon · CPC title

• C08G12/00

  Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen (aminophenols C08G8/16) · CPC title

• C08G73/02

  Polyamines · CPC title

• C08G79/02

  a linkage containing phosphorus · CPC title