Covalently-bound polybromocyclododecane flame retardants

Patent metadata

Field	Value
Publication number	US-11072744-B2
Application number	US-201816157221-A
Country	US
Kind code	B2
Filing date	Oct 11, 2018
Priority date	Oct 11, 2018
Publication date	Jul 27, 2021
Grant date	Jul 27, 2021

Abstract

A polybrominated flame-retardant compound, a process for forming a flame-retardant material, and an article of manufacture are disclosed. The polybrominated flame-retardant compound includes a cyclododecane moiety, at least two bromo groups, and at least one substituent having a reactive functional group. The process includes forming a polybromocyclododecane (PBCD) compound having at least one reactive functional group and incorporating the PBCD compound into a polymer in a process that includes covalent binding of the PBCD compound. The article of manufacture includes a flame-retardant material that comprises a polymer with a covalently-bound PBCD compound.

First claim

What is claimed is:

1. A polybrominated flame-retardant compound, comprising:
a cyclododecane moiety;
at least two bromo groups; and
at least one substituent having a reactive functional group selected from the group consisting of an allyl group, an epoxide, an acryloyl group, a methacryloyl group, a propylene carbonate group, an oxalate group, an amine group, and an amide group.

2. The polybrominated flame-retardant compound of claim 1 , wherein the at least two bromo groups are bound to the cyclododecane moiety.

3. The polybrominated flame-retardant compound of claim 1 , wherein at least one of the at least two bromo groups is bound to the at least one substituent.

4. The polybrominated flame-retardant compound of claim 1 , wherein the at least one substituent includes the allyl group.

5. The polybrominated flame-retardant compound of claim 1 , wherein the at least one substituent includes a thioether linker.

6. The polybrominated flame-retardant compound of claim 1 , wherein the at least one substituent includes a benzyl moiety.

7. The polybrominated flame-retardant compound of claim 1 , wherein the at least one substituent is linked to the cyclododecane moiety by an oxygen atom linker or an ester linker.

8. The polybrominated flame-retardant compound of claim 1 , further comprising at least one additional substituent having a reactive functional group selected from the group consisting of a hydroxyl group, an epoxide group, a vinyl group, an acryloyl group, a methacryloyl group, a propylene carbonate group, an oxalate group, a carboxylic acid group, an amine group, and an amide group.

9. A process of forming a flame-retardant material, comprising:
providing the polybrominated flame-retardant compound of claim 1 ; and
incorporating the polybrominated flame-retardant compound into a polymer, wherein the incorporating includes covalent binding of the at least one reactive functional group to the polymer.

10. The process of claim 9 , wherein the providing the the polybrominated flame-retardant compound comprises:
selecting a substituent having the at least one reactive functional group;
providing a compound having the selected substituent; and
reacting the compound having the selected substituent with a brominated precursor, wherein the reaction causes the selected substituent to attach to the brominated precursor.

11. The process of claim 10 , wherein the compound having the selected substituent is selected from the group consisting of a chloroacetate ester, a chloro-enone, 2-chloroacetamide, epichlorohydrin, and allyl chloride.

12. The process of claim 10 , wherein the compound having the selected substituent is selected from the group consisting of a glycolic acid, a glycolate ester, a hydroxy-substituted enone, N-hydroxyacetamide, an acryloyl benzyl alcohol, methacryloyl benzyl alcohol, glycidol, and allyl alcohol.

13. The process of claim 10 , wherein the brominated precursor includes at least two bromo groups and at least one hydroxyl group.

14. The process of claim 9 , wherein the polymer is selected from the group consisting of a polystyrene, an epoxide resin, a polyhydroxyurethane, a polycarbonate, a polyester, a polyacrylate, a polyimide, a polyamide, a polyurea, and a poly(vinyl-ester).

15. An article of manufacture comprising a flame-retardant material, the flame-retardant material comprising:
a polymer; and
the polybrominated flame-retardant compound of claim 1 covalently bound to the polymer.

16. The article of manufacture of claim 15 , wherein the polybrominated flame-retardant compound acts as a crosslinker in the polymer.

17. The article of manufacture of claim 15 , wherein the polymer is selected from the group consisting of a polystyrene, an epoxide resin, a polyhydroxyurethane, a polycarbonate, a polyester, a polyacrylate, a polyimide, a polyamide, a polyurea, and a poly(vinyl-ester).

18. The article of manufacture of claim 15 , further comprising an electronic component.

19. The article of manufacture of claim 15 , further comprising a printed circuit board.

20. The article of manufacture of claim 15 , wherein the polybrominated flame-retardant compound includes a cyclododecane moiety with four bromo groups.

Assignees

• IBM

Inventors

• Kobilka Brandon M
• Kuczynski Joseph
• Wertz Jason T
• King Scott B

Classifications

• C07C31/272

  Monocyclic · CPC title

• C07C69/54

  Acrylic acid esters; Methacrylic acid esters · CPC title

• C08J2300/00

  Characterised by the use of unspecified polymers · CPC title

• C07C323/12

  the carbon skeleton being acyclic and saturated · CPC title

• C08J2369/00

  Characterised by the use of polycarbonates; Derivatives of polycarbonates · CPC title