Flame-retardant vanillin-derived small molecules

Patent metadata

Field	Value
Publication number	US-10214693-B2
Application number	US-201715584866-A
Country	US
Kind code	B2
Filing date	May 2, 2017
Priority date	May 2, 2017
Publication date	Feb 26, 2019
Grant date	Feb 26, 2019

Abstract

A flame-retardant vanillin-derived small molecule, a process for forming a flame-retardant polymer, and an article of manufacture comprising a material that contains the flame-retardant vanillin-derived small molecule are disclosed. The flame-retardant vanillin-derived small molecule can be synthesized from vanillin 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 a diol vanillin derivative and a flame-retardant phosphorus-based molecule to form the flame-retardant vanillin-derived small molecule, and binding the flame-retardant vanillin-derived small molecule to a polymer. The material in the article of manufacture can be flame-retardant, and contain the flame-retardant vanillin-derived small molecules. 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 flame-retardant vanillin-derived small molecule with a formula of:

wherein M is a flame-retardant substituent;
wherein FR is a 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.

2. The flame-retardant vanillin-derived small molecule of claim 1 , wherein the M is a substituent selected from a group consisting of substituents with formulas of:

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

3. The flame-retardant vanillin-derived small molecule of claim 1 , wherein the PR is a phosphoryl moiety with a formula of:

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

5. The flame-retardant vanillin-derived small molecule of claim 1 , wherein the thioether substituent is selected from a group consisting of thioether substituents with formulas of:

6. The flame-retardant vanillin-derived small molecule of claim 1 , wherein, the vanillin from a bio-based source is a starting material for the flame-retardant vanillin-derived small molecule.

7. The flame-retardant vanillin-derived small molecule of claim 1 , wherein the flame-retardant vanillin-derived small molecule is blended with a polymer.

Assignees

• IBM

Inventors

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

Classifications

• C08K5/5337

  containing also halogens · CPC title

• C07F9/4419

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

• C08K5/5399

  Phosphorus bound to nitrogen · CPC title

• C08K5/372

  Sulfides {, e.g. R-(S)x-R'} · CPC title

• C08K5/3725

  containing nitrogen · CPC title