Flame retardants derived from biobased dicarboxylic acids

Patent metadata

Field	Value
Publication number	US-11279816-B2
Application number	US-201916444611-A
Country	US
Kind code	B2
Filing date	Jun 18, 2019
Priority date	Jun 18, 2019
Publication date	Mar 22, 2022
Grant date	Mar 22, 2022

Abstract

A biobased flame retardant, a process for forming a biobased flame retardant, and an article of manufacture. The flame-retardant compound includes at least one moiety derived from a biobased dicarboxylic acid and at least one organophosphorus moiety. The process includes providing an organophosphorus compound and malic acid or a hydroxylated derivative of a biobased dicarboxylic acid. The process also includes reacting the organophosphorus compound and the malic acid or hydroxylated derivative to form a flame retardant. The article of manufacture includes a polymer and an organophosphorus flame retardant derived from a biobased dicarboxylic acid.

First claim

What is claimed is:

1. A flame-retardant compound
having the structure:

wherein each L is an organophosphorus moiety.

2. The flame-retardant compound of claim 1 , wherein the flame-retardant compound is derived from malic acid.

3. The flame-retardant compound of claim 1 , wherein the organophosphorus moiety has an organic substituent with a reactive functional group.

4. The flame-retardant compound of claim 3 , wherein the reactive functional group is selected from the group consisting of an aldehyde, a halide, an epoxy, a carboxylate, a vinyl, a propylene carbonate, an imine, an imide, an amine, an amide, and a thiol.

5. The flame-retardant compound of claim 1 , wherein the organophosphorus moiety has a formula selected from the group consisting of:

where R and R′ are organic substituents.

6. The flame-retardant compound of claim 5 , wherein at least one of the R and the R′ is an alkyl substituent.

7. The flame-retardant compound of claim 5 , wherein the at least one of the R and the R′ is a substituent selected from the group consisting of a methyloxirane, an allyl, and a propylene carbonate.

8. An article of manufacture, comprising:
a polymer; and
a flame retardant, wherein the flame retardant is an additive flame retardant or covalently bound to the polymer, and wherein the flame retardant has the structure:

wherein each L is an organophosphorus moiety.

9. The article of manufacture of claim 8 , further comprising an electronic component.

10. The article of manufacture of claim 8 , wherein the polymer is selected from the group consisting of polystyrenes, epoxide resins, polyhydroxyurethanes, polycarbonates, polyesters, polyacrylates, polyimides, polyamides, polyureas, and poly(vinyl-esters).

11. The article of manufacture of claim 8 , wherein the flame retardant is an additive flame retardant.

12. The article of manufacture of claim 8 , wherein the flame retardant is covalently bound to the polymer.

13. The article of manufacture of claim 8 , wherein the flame retardant is a monomer unit in the polymer.

14. A process, comprising:
providing a hydroxyl-protected biobased malic acid;
providing an organophosphorus compound;
reacting the organophosphorus compound and the hydroxyl-protected biobased malic acid to form a flame retardant intermediate; and
deprotecting the flame retardant intermediate to form a flame retardant having the following structure:

wherein each L is an organophosphorus moiety.

15. The process of claim 14 , further comprising polymerizing the flame retardant.

16. The process of claim 14 , further comprising blending the flame retardant with a polymer as an additive flame retardant.

17. The process of claim 14 , further comprising covalently binding the flame retardant to a polymer.

18. The process of claim 14 , further comprising carrying out a reaction involving at least one functional group on the flame retardant.

19. The process of claim 14 , wherein the organophosphorus compound is selected from the group consisting of a chlorophosphate ester, a phosphonate ester, a phosphinate ester, and phosphorus oxychloride.

Assignees

• IBM

Inventors

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

Classifications

• C08L75/06

  from polyesters · CPC title

• C08L2201/02

  Flame or fire retardant/resistant · CPC title

• C08L75/02

  Polyureas · CPC title

• C08K5/5337 Primary

  containing also halogens · CPC title

• C08K3/016

  Flame-proofing or flame-retarding additives · CPC title