Lysine and proline based flame retardants

Patent metadata

Field	Value
Publication number	US-10329488-B2
Application number	US-201715726248-A
Country	US
Kind code	B2
Filing date	Oct 5, 2017
Priority date	Oct 5, 2017
Publication date	Jun 25, 2019
Grant date	Jun 25, 2019

Abstract

A flame retardant lysine-based derivative, a process for forming a flame retardant lysine-based derivative, and an article of manufacture comprising a flame retardant lysine-based derivative are disclosed. The flame retardant lysine-derived molecule can be synthesized from a bio-based source, and can have at least one phosphoryl or phosphonyl moiety. A flame retardant proline-based derivative, a process for forming a flame retardant proline-based derivative, and an article of manufacture comprising a flame retardant proline-based derivative are also disclosed. The flame retardant proline-derived molecule can be synthesized from a bio-based source and can have at least one phosphoryl or phosphonyl moiety.

First claim

What is claimed is:

1. A flame retardant lysine-derived molecule with a formula of:

wherein X is selected from a group consisting of a methanediyl moiety and a carbonyl moiety;
wherein FR is a phosphorus-based moiety;
wherein R 1 is a substituent selected from a group consisting of an allyl substituent, an epoxide substituent, a propylene carbonate substituent, a phenyl substituent, and a thioether substituent;
wherein R 2 is a substituent selected from a group consisting of an allyl substituent, an epoxide substituent, a propylene carbonate substituent, a phenyl substituent, and a thioether substituent;
wherein R 3 is a substituent selected from a group consisting of an allyl substituent, an epoxide substituent, a propylene carbonate substituent, a phenyl substituent, and a thioether substituent.

2. The flame retardant lysine-derived molecule of claim 1 , wherein the FR is a phosphoryl moiety with a formula of:

3. The flame retardant lysine-derived molecule of claim 1 , wherein the FR is a phosphonyl moiety with a formula of:

4. The flame retardant lysine-derived molecule of claim 1 , wherein R 1 is the phenyl substituent, wherein R 2 is the phenyl substituent, and wherein R 3 is the phenyl substituent.

5. The flame retardant lysine-derived molecule of claim 1 , wherein R 1 is the epoxide substituent, wherein R 2 is the epoxide substituent, and wherein R 3 is the epoxide substituent.

6. The flame retardant lysine-derived molecule of claim 1 , wherein R 1 is the allyl substituent, wherein R 2 is the allyl substituent, and wherein R 3 is the allyl substituent.

7. The flame retardant lysine-derived molecule of claim 1 , wherein R 1 is the propylene carbonate substituent, wherein R 2 is the propylene carbonate substituent, and wherein R 3 is the propylene carbonate substituent.

8. The flame retardant lysine-derived molecule of claim 1 , wherein the thioether substituent is selected from a group consisting of a hydroxyl-functionalized thioether substituent, an amino-functionalized thioether substituent, and a carboxylic acid-functionalized thioether substituent.

9. The flame retardant lysine-derived molecule of claim 1 , wherein R 1 is the phenyl substituent, wherein R 3 is the phenyl substituent, and wherein R 2 is not the phenyl substituent.

10. The flame retardant lysine-derived molecule of claim 1 , wherein R 1 is not the phenyl substituent, wherein R 3 is not the phenyl substituent, and wherein R 2 is the phenyl substituent.

11. A flame retardant proline-derived molecule with a formula of:

wherein X is selected from a group consisting of a methanediyl moiety and a carbonyl moiety;
wherein FR is a phosphorus-based moiety;
wherein R 1 is a substituent selected from a group consisting of an allyl substituent, an epoxide substituent, a propylene carbonate substituent, a phenyl substituent, and a thioether substituent;
wherein R 2 is a substituent selected from a group consisting of an allyl substituent, an epoxide substituent, a propylene carbonate substituent, a phenyl substituent, and a thioether substituent.

12. The flame retardant proline-derived molecule of claim 11 , wherein the FR is a phosphoryl moiety with a formula of:

13. The flame retardant proline-derived molecule of claim 11 , wherein the FR is a phosphonyl moiety with a formula of:

14. The flame retardant proline-derived molecule of claim 11 , wherein R 1 is the phenyl substituent and wherein R 2 is the phenyl substituent.

15. The flame retardant proline-derived molecule of claim 11 , wherein R 1 is the epoxide substituent and wherein R 2 is the epoxide substituent.

16. The flame retardant proline-derived molecule of claim 11 , wherein R 1 is the allyl substituent and wherein R 2 the allyl substituent.

17. The flame retardant proline-derived molecule of claim 11 , wherein R 1 is the propylene carbonate substituent and wherein R 2 is the propylene carbonate substituent.

18. The flame retardant proline-derived molecule of claim 11 , wherein the thioether substituent is selected from a group consisting of a hydroxyl-functionalized thioether substituent, an amino-functionalized thioether substituent, and a carboxylic acid-functionalized thioether substituent.

19. The flame retardant proline-derived molecule of claim 11 , wherein R 1 is a phenyl substituent and wherein R 2 is not a phenyl substituent.

20. An article of manufacture, comprising a material containing the flame retardant lysine-derived molecule of claim 1 , wherein the article of manufacture further comprises a printed circuit board (PCB).

Assignees

• IBM

Inventors

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

Classifications

• C08K3/32

  Phosphorus-containing compounds · CPC title

• C09K21/10 Primary

  containing nitrogen · CPC title

• C08K2003/329

  Phosphorus containing acids · CPC title

• C07D207/04

  having no double bonds between ring members or between ring members and non-ring members · CPC title

• C07C211/12

  1,6-Diaminohexanes · CPC title