Flame-retardant aconitic acid-derived cross-linkers

Patent metadata

Field	Value
Publication number	US-10301436-B2
Application number	US-201715611360-A
Country	US
Kind code	B2
Filing date	Jun 1, 2017
Priority date	Jun 1, 2017
Publication date	May 28, 2019
Grant date	May 28, 2019

Abstract

A flame-retardant aconitic acid-derived cross-linker, a process for forming a flame-retardant resin, and an article of manufacture comprising a material that contains a flame-retardant aconitic acid-derived cross-linker are disclosed. The flame-retardant aconitic acid-derived cross-linker can have at least two phosphoryl or phosphonyl moieties with allyl functional groups, epoxy functional groups, propylene carbonate functional group, or functionalized thioether substituents. The process for forming the flame-retardant polymer can include forming an aconitic acid derivative, forming a phosphorus-based flame-retardant molecule, and reacting the aconitic acid derivative with the phosphorus-based flame-retardant molecule to form a flame-retardant aconitic acid-derived cross-linker, and binding the cross-linker to a polymer. The aconitic acid derivative can be synthesized from aconitic acid obtained from a bio-based source. Examples of aconitic acid derivatives include carboxysuccinic acid, 2-(hydroxymethyl)-1,4-butenediol, and 2-(hydroxymethyl)-1,4-butanediol. The article of manufacture can further comprise an electronic component.

First claim

What is claimed is:

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

and
at least two functional groups, wherein the at least two functional groups bind to a polymer at at least two positions.

2. The flame-retardant aconitic acid-derived cross-linker of claim 1 , wherein the flame-retardant aconitic acid-derived cross-linker has a structure selected from a group consisting of molecules with formulas of:

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

3. The flame-retardant aconitic acid-derived cross-linker of claim 2 , wherein the functionalized 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.

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

5. 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 a flame-retardant aconitic acid-derived cross-linker; and
binding the flame-retardant aconitic acid-derived cross-linker to a polymer to form the flame-retardant polymer.

6. The of claim 5 , wherein the aconitic acid derivative is synthesized from aconitic acid that has been obtained from a bio-based source.

7. The process of claim 6 , wherein the bio-based source is citric acid.

8. The process of claim 5 , wherein the phosphorus-based flame-retardant molecule is selected from a group consisting of phosphorus-based molecules with formulas of:

wherein R is selected from a group consisting of an allyl functional group and an epoxy functional group.

9. The process of claim 5 , further comprising chemically reacting the flame-retardant aconitic acid-derived cross-linker with a thiol molecule to form a thioether-linked flame-retardant aconitic acid-derived cross-linker.

10. The process of claim 9 , wherein the thiol molecule is selected from a group consisting of 2-mercaptoethanol, cysteamine hydrochloride, and 3-mercaptopropionate.

11. The process of claim 5 , further comprising chemically reacting the flame-retardant aconitic acid-derived cross-linker with lithium bromide and carbon dioxide to form a propylene carbonate-functionalized flame-retardant aconitic acid-derived cross-linker.

12. An article of manufacture, comprising:
a material containing a flame-retardant aconitic acid-derived cross-linker, the cross-linker 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.

13. The article of manufacture of claim 12 , wherein the flame-retardant aconitic acid-derived cross-linker is synthesized from aconitic acid obtained from a bio-based source.

14. The article of manufacture of claim 13 , wherein the bio-based source is citric acid.

15. The article of manufacture of claim 12 , wherein the material is selected from a group consisting of an adhesive, a resin, and a polymer.

16. The article of manufacture of claim 15 , wherein the polymer is 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).

17. The article of manufacture of claim 12 , further comprising an electronic component.

Assignees

• IBM

Inventors

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

Classifications

• C07F9/113

  with unsaturated acyclic alcohols · CPC title

• H05K1/032 Primary

  consisting of one material · CPC title

• C08G81/027 Primary

  containing polyester or polycarbonate sequences · CPC title

• C08L2201/02

  Flame or fire retardant/resistant · CPC title

• C07C69/003

  Esters of saturated alcohols having the esterified hydroxy group bound to an acyclic carbon atom · CPC title