Limonene-based, non-halogenated flame retardants for polymeric applications

Patent metadata

Field	Value
Publication number	US-2020140468-A1
Application number	US-202016732994-A
Country	US
Kind code	A1
Filing date	Jan 2, 2020
Priority date	Dec 4, 2017
Publication date	May 7, 2020
Grant date	—

Abstract

A limonene-based flame-retardant compound, a method of making a flame-retardant polymer, and an article of manufacture comprising a material that includes a limonene-based flame-retardant compound are provided. In an embodiment, the method includes forming a limonene-based derivative; forming a phosphorus-based flame-retardant molecule; reacting the limonene-based derivative with the phosphorus-based flame-retardant molecule to form a limonene-based flame-retardant compound; and forming a flame-retardant polymer from the limonene-based flame-retardant compound. In some embodiments, the limonene-based flame-retardant compound has variable functionality including vinyl, epoxide, methylene bridges, and thioethers.

First claim

What is claimed is:

1 . A limonene-based flame-retardant compound having the structure

wherein:
each FR includes a phosphate group; and
each R is independently alkyl, substituted alkyl, alkenyl, or substituted alkenyl.

2 . The limonene-based flame-retardant compound of claim 1 , wherein the substituted alkenyl includes an alkene functional group.

3 . The limonene-based flame-retardant compound of claim 1 , wherein the substituted alkyl includes an epoxide functional group.

4 . The limonene-based flame-retardant compound of claim 1 , wherein the substituted alkyl includes a carbonate functional group.

5 . The limonene-based flame-retardant compound of claim 1 , wherein the substituted alkyl independently includes one or more of

wherein:
y is an integer between 1 and 12, and
the dotted line bond indicates a connection to the phosphate group.

6 . The limonene-based flame-retardant compound of claim 1 , wherein is a hydroxyl-functionalized limonene.

7 . The limonene-based flame-retardant compound of claim 1 , wherein the substituted alkenyl is

wherein:
y is an integer between 1 and 12, and
the dotted line bond indicates a connection to the phosphate group.

8 . A method of forming a limonene-based flame-retardant polymer, comprising:
forming a limonene-based derivative; forming a phosphorus-based flame-retardant molecule; reacting the limonene-based derivative with the phosphorus-based flame-retardant molecule to form a limonene-based flame-retardant compound; and forming a flame-retardant polymer from the limonene-based flame-retardant compound.

9 . The method of claim 8 , wherein the limonene-based derivative is synthesized from limonene that has been obtained from a bio-based source.

10 . The method of claim 8 , wherein the limonene-based derivative comprises one or more hydroxyl groups.

11 . The method of claim 8 , wherein the phosphorus-based flame-retardant molecule includes a phosphate group or a phosphonate group.

12 . The method of claim 11 , wherein the phosphate group is represented by formula

and the phosphonate group is represented by formula

wherein:
X is chlorine or hydroxyl,
R′ is alkyl, substituted alkyl, aryl, or substituted aryl, and
R is an allyl group, an alkenyl group, an epoxy group, a carbonate group, or a thioether group.

13 . The method of claim 8 , wherein the forming a flame-retardant polymer comprises performing a base-initiated polymerization or a Ziegler-Natta type polymerization.

14 . The method of claim 8 , wherein the limonene-based flame-retardant compound is incorporated into the polymer by chemically bonding the limonene-based flame-retardant compound to one or more polymer chains.

15 . The method of claim 8 , wherein the limonene-based flame-retardant compound is incorporated into the polymer by blending or by a polymerization reaction.

16 . The method of claim 15 , wherein the polymerization reaction includes at least one additional monomer.

17 . An article of manufacture, comprising:
a material containing a limonene-based flame-retardant polymer.

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

19 . The article of manufacture of claim 17 , wherein the material is an adhesive.

20 . The article of manufacture of claim 17 , wherein the material is a plastic for integrated circuit packaging.

Assignees

• IBM

Inventors

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

Classifications

• C07F9/4081

  Esters with cycloaliphatic alcohols · CPC title

• C07F9/12

  with hydroxyaryl compounds · CPC title

• C07F9/113

  with unsaturated acyclic alcohols · CPC title

• C07F9/1406

  containing the structure Hal-P(=O)-O-aryl · CPC title

• C07F9/3217

  Esters of acyclic unsaturated acids · CPC title