Flame-retardant vanillin-derived cross-linkers

Patent metadata

Field	Value
Publication number	US-10167427-B2
Application number	US-201715584798-A
Country	US
Kind code	B2
Filing date	May 2, 2017
Priority date	May 2, 2017
Publication date	Jan 1, 2019
Grant date	Jan 1, 2019

Abstract

A flame-retardant vanillin-derived cross-linker, a process for forming a flame-retardant polymer, and an article of manufacture comprising a material that contains the flame-retardant vanillin-derived cross-linker are disclosed. The flame-retardant vanillin-derived cross-linker 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 polymer can include reacting a diol vanillin derivative and a flame-retardant phosphorus-based molecule to form the flame-retardant vanillin-derived cross-linker, and binding the flame-retardant vanillin-derived cross-linker to a polymer. The material in the article of manufacture can be flame-retardant, and contain flame-retardant vanillin-derived cross-linkers. 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 cross-linker 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 an allyl substituent, an epoxide substituent, a propylene carbonate substituent, and a thioether substituent.

2. The flame-retardant vanillin-derived cross-linker of claim 1 , wherein the M is 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 allyl substituent, the epoxide substituent, the propylene carbonate substituent, and the thioether substituent.

3. The flame-retardant vanillin-derived cross-linker of claim 1 , wherein the FR is a phosphoryl moiety with a formula of:

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

5. The flame-retardant vanillin-derived cross-linker of claim 1 , wherein the 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.

6. The flame-retardant vanillin-derived cross-linker of claim 1 , wherein the flame-retardant vanillin-derived cross-linker has one phosphoryl moiety and one phosphonyl moiety.

7. The flame-retardant vanillin-derived cross-linker of claim 1 , wherein the flame-retardant vanillin-derived cross-linker is bound to a polymer.

Assignees

• IBM

Inventors

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

Classifications

• C07D317/12

  with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms · CPC title

• C08K5/5337

  containing also halogens · CPC title

• C08K5/5313

  Phosphinic compounds, e.g. R2=P(:O)OR' · CPC title

• C12P7/26

  Ketones · CPC title

• C08K5/5317

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