Flame-retardant aconitic acid-derived small molecules

Patent metadata

Field	Value
Publication number	US-10280287-B2
Application number	US-201715611237-A
Country	US
Kind code	B2
Filing date	Jun 1, 2017
Priority date	Jun 1, 2017
Publication date	May 7, 2019
Grant date	May 7, 2019

Abstract

A flame-retardant aconitic acid-derived small molecule, a process for forming a flame-retardant polymer, and an article of manufacture comprising a material that contains a flame-retardant aconitic acid-derived small molecule are disclosed. The flame-retardant aconitic acid-derived small molecule can be synthesized from aconitic acid obtained from a bio-based source, and can have at least one phosphoryl or phosphonyl moiety with phenyl, allyl, or thioether substituents. The process for forming the flame-retardant polymer can include reacting an aconitic acid derivative with a flame-retardant phosphorus-based molecule to form a flame-retardant aconitic acid-derived small molecule, and combining the flame-retardant aconitic acid-derived small molecule with a polymer. The material in the article of manufacture can be a resin, adhesive, polymer, etc.

First claim

What is claimed is:

1. A flame-retardant aconitic acid-derived small molecule comprising:
at least one phosphorus-based moiety with a formula selected from a group of formulas consisting of:

and
at least one substituent bound to the at least one phosphorus-based moiety.

2. The flame-retardant aconitic acid-derived small molecule of claim 1 , wherein the flame-retardant aconitic acid-derived small molecule is selected from a group of aconitic acid-derived small molecules with formulas of:

wherein FR is the at least one phosphorus-based moiety; and
wherein R is a substituent selected from a group consisting of a phenyl substituent, an allyl substituent, and a thioether substituent.

3. The flame-retardant aconitic acid-derived small molecule of claim 2 , wherein the thioether substituent is selected from a group consisting of thioether substituents with formulas of:

4. The flame-retardant aconitic acid-derived small molecule of claim 1 , wherein the flame-retardant aconitic acid-derived small molecule is synthesized from aconitic acid obtained from a bio-based source.

5. The flame-retardant aconitic acid-derived small molecule of claim 1 , wherein the flame-retardant aconitic acid-derived small molecule is blended with a polymer.

6. A process of forming a flame-retardant polymer, comprising:
forming a phosphorus-based flame-retardant molecule;
forming an aconitic acid derivative selected from a group consisting of carboxysuccinic acid, 2-(hydroxymethyl)-1,4-butenediol, and 2-(hydroxymethyl)-1,4-butanediol;
chemically reacting the aconitic acid derivative with the phosphorus-based flame-retardant molecule to form an aconitic acid-based flame-retardant small molecule; and
combining the flame-retardant aconitic acid-derived small molecule with a polymer to form the flame-retardant polymer.

7. The process of claim 6 , wherein the aconitic acid derivative is synthesized from aconitic acid obtained from a bio-based source.

8. The process of claim 7 , wherein the bio-based source is citric acid.

9. The process of claim 6 , wherein the phosphorus-based flame-retardant molecule is selected from a group consisting of phosphorus-based molecules with formulas of:

wherein R is a substituent selected from a group consisting of a phenyl substituent and an allyl substituent.

10. The process of claim 6 , wherein the phosphorus-based flame-retardant molecule is a thiol molecule with a formula of:

11. The process of claim 6 , wherein the phosphorus-based flame-retardant molecule is a thiol molecule with a formula of:

12. The process of claim 6 , wherein the phosphorus-based flame-retardant molecule is a thiol molecule with a formula of:

13. An article of manufacture, comprising:
a material containing a flame-retardant aconitic acid-derived small molecule, comprising:
at least one phosphorus-based moiety with a formula selected from a group of formulas consisting of:

and
at least one substituent bound to the at least one phosphorus-based moiety.

14. The article of manufacture of claim 13 , wherein the material is a resin in a printed circuit board.

15. The article of manufacture of claim 13 , wherein the flame-retardant aconitic acid derived small molecules is synthesized from aconitic obtained from a bio-based source.

16. The article of manufacture of claim 13 , wherein the material is selected from a group consisting of an adhesive and a plastic.

17. The article of manufacture of claim 13 , wherein the material is a polymer selected from a group consisting of polyurethane, an epoxy, a polyhydroxyurethane, a polycarbonate, a polyester, a polyacrylate, a polyimide, a polyamide, a polyurea, and a poly(vinyl-ester).

Assignees

• IBM

Inventors

• Czaplewski Sarah K
• Kobilka Brandon M
• Kuczynski Joseph
• Wertz Jason T
• Zhang Jing

Classifications

• H05K1/0326

  containing O · CPC title

• C07F9/2458

  of aliphatic amines · CPC title

• C08K5/524

  Esters of phosphorous acids, e.g. of H3PO3 · CPC title

• C08K5/521

  Esters of phosphoric acids, e.g. of H3PO4 · CPC title

• H05K2201/012

  Flame-retardant; Preventing of inflammation · CPC title