Flame-retardant vanillin-derived monomers

Patent metadata

Field	Value
Publication number	US-10689580-B2
Application number	US-201916371689-A
Country	US
Kind code	B2
Filing date	Apr 1, 2019
Priority date	May 2, 2017
Publication date	Jun 23, 2020
Grant date	Jun 23, 2020

Abstract

A flame-retardant vanillin-derived monomer, a process for forming a flame-retardant polymer, and an article of manufacture comprising a material that contains flame-retardant vanillin-derived monomer are disclosed. The flame-retardant vanillin-derived monomer can be synthesized from vanillin obtained from a bio-based source, and can have at least one phosphoryl or phosphonyl moiety with phenyl, allyl, epoxide, or propylene carbonate substituents. The process for forming the flame-retardant polymer can include reacting a vanillin derivative and a flame-retardant phosphorus-based molecule to form the flame-retardant vanillin-derived monomer, and then polymerizing the flame-retardant vanillin-derived monomer. The material in the article of manufacture can be flame-retardant, and contain the flame-retardant vanillin-derived monomer. Examples of materials that can be in the article of manufacture can include resins, plastics, adhesives, polymers, etc.

First claim

What is claimed is:

1. A process of forming a flame-retardant polymer, comprising:
forming a phosphorus-based flame-retardant molecule selected from the group consisting of a chlorophosphate-based molecule and a phosphonate-based molecule;
forming a vanillin derivative;
chemically reacting the vanillin derivative with the phosphorus-based flame-retardant molecule to form a flame-retardant vanillin-derived monomer; and
polymerizing the flame-retardant vanillin-derived monomer.

2. The process of claim 1 , wherein the vanillin derivative is synthesized from vanillin that has been obtained from a bio-based source.

3. The process of claim 1 , wherein the vanillin derivative is a diol vanillin derivative selected from a group consisting of:
a phenol diol vanillin derivative with a formula of:

a carboxylic acid diol vanillin derivative with a formula of:

and
a benzyl alcohol diol vanillin derivative with a formula of:

4. The process of claim 1 , wherein the vanillin derivative is a flame-retardant vanillin derivative selected from a group consisting of:
a flame-retardant phenol vanillin derivative with a formula of:

wherein FR is a phosphorus-based moiety and Ph is a phenyl substituent,
a flame-retardant carboxylic acid vanillin derivative with a formula of:

wherein FR is a phosphorus-based moiety and Ph is a phenyl substituent, and
a flame-retardant benzyl alcohol vanillin derivative with a formula of:

wherein FR is a phosphorus-based moiety and Ph is a phenyl substituent.

5. The process of claim 4 , wherein the FR is a phosphoryl moiety with a formula of:

wherein Ph is a phenyl substituent.

6. The process of claim 4 , wherein the FR is a phosphonyl moiety with a formula of:

wherein Ph is a phenyl substituent.

7. The process of claim 1 , wherein the phosphorus-based flame-retardant molecule has a formula of:

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

8. The process of claim 1 , wherein the phosphorus-based flame-retardant molecule has a formula of:

wherein Ph is a phenyl substituent and R is a substituent selected from the group consisting of the epoxide substituent and the allyl substituent.

9. The process of claim 1 , further comprising chemically reacting the flame-retardant vanillin-derived monomer with lithium bromide and carbon dioxide to form a flame-retardant vanillin-derived monomer with at least one propylene carbonate substituent.

Assignees

• IBM

Inventors

• Kobilka Brandon M
• Kuczynski Joseph
• Porter Jacob T
• Wertz Jason T

Classifications

• C07F9/4021

  Esters of aromatic acids (P-C aromatic linkage) · CPC title

• C07F9/65515

  the oxygen atom being part of a five-membered ring · CPC title

• C07F9/1406

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

• C07C15/04

  Benzene · CPC title

• C09K21/14

  Macromolecular materials · CPC title