Bondable flame-retardant vanillin-derived molecules

Patent metadata

Field	Value
Publication number	US-10689577-B2
Application number	US-201816212954-A
Country	US
Kind code	B2
Filing date	Dec 7, 2018
Priority date	May 2, 2017
Publication date	Jun 23, 2020
Grant date	Jun 23, 2020

Abstract

A flame-retardant vanillin-derived molecule, a process for forming a flame-retardant resin, and an article of manufacture comprising a material that contains the flame-retardant vanillin-derived molecule are disclosed. The flame-retardant vanillin-derived 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, epoxide, propylene carbonate, or thioether substituents. The process for forming the flame-retardant resin can include reacting a vanillin derivative and a flame-retardant phosphorus-based molecule to form the flame-retardant vanillin-derived molecule, and binding the flame-retardant vanillin-derived molecule to a resin. The flame-retardant vanillin-derived molecules can also be bound to polymers. The material in the article of manufacture can be flame-retardant, and contain the flame-retardant vanillin-derived 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 process of forming a flame-retardant resin, 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 molecule; and
binding the flame-retardant vanillin-derived molecule to a resin to form the flame-retardant resin.

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 selected from a group consisting of:
a phenol vanillin derivative with a formula of:

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

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

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

4. 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.

5. 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.

6. The process of claim 1 , further comprising chemically reacting the flame-retardant vanillin-derived molecule with a thiol molecule to form a flame-retardant vanillin-derived molecule with a thioether substituent.

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

Assignees

• IBM

Inventors

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

Classifications

• C09K21/12 Primary

  containing phosphorus · CPC title

• C08K5/5317

  Phosphonic compounds, e.g. R—P(:O)(OR')2 · CPC title

• C07F9/65502

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

• C07F9/1403

  containing the structure Hal-P(=O)-O-unsaturated acyclic group · CPC title

• C07F9/08

  Esters of oxyacids of phosphorus {(C07F9/062 takes precedence)} · CPC title