Impact resistant flame retardant polyhexahydrotriazine polymers via generation of polyhexahydrotriazine monomers and hexahydro-1,3,5-triazine small molecules

Patent metadata

Field	Value
Publication number	US-11008422-B2
Application number	US-201916556563-A
Country	US
Kind code	B2
Filing date	Aug 30, 2019
Priority date	Aug 10, 2017
Publication date	May 18, 2021
Grant date	May 18, 2021

Abstract

An impact resistant polyhexahydrotriazine polymer, processes of forming an impact resistant polyhexahydrotriazine polymer, and an article of manufacture comprising an impact resistant polyhexahydrotriazine polymer are disclosed. The impact resistant polyhexahydrotriazine polymer includes at least one hexahydrotriazine group and at least one chain comprising an allylic portion and a styrenic portion. Variations in the chain control properties of the impact resistant polymer. The process of forming the impact resistant polyhexahydrotriazine polymer includes reactions between formaldehyde and at least two classes of monomer that form hexahydrotriazine groups and impact resistant chains. Adjusting relative monomer concentrations controls properties of the impact resistant polyhexahydrotriazine polymer. The article of manufacture contains a material that has an impact resistant polymer. Impact resistance of the impact resistant polyhexahydrotriazine polymer is dependent upon variation in relative amounts of monomers used in its synthesis.

First claim

What is claimed is:

1. A process of forming an impact resistant polyhexahydrotriazine polymer, comprising:
providing an aromatic amine monomer;
providing one or more additional monomers, wherein at least one of the one or more additional monomers is an allylic compound;
providing formaldehyde;
forming a hexahydrotriazine compound in a reaction between the formaldehyde and the aromatic amine monomer; and
reacting the hexahydrotriazine compound with the one or more additional monomers in a polymerization reaction.

2. The process of claim 1 , wherein at least one of the one or more additional monomers is a flame retardant monomer.

3. The process of claim 2 , wherein the flame retardant monomer is selected from the group consisting of a phosphorus-containing compound, a melamine compound, a halogen, a halogen-containing compound, and a dianiline compound.

4. The process of claim 1 , wherein at least one of the one or more additional monomers further comprises a styrenic compound.

5. The process of claim 1 , wherein the aromatic amine is an amino-functionalized diphenyl ether compound.

6. The process of claim 1 , further comprising blending the impact resistant polyhexahydrotriazine polymer with a material selected from the group consisting of polyhemiaminal, a carbon filler, an epoxy, a polyhydroxyurethane, a polycarbonate, a polyester, a polyacrylate, a polyimide, a polyamide, a polyurea, and a poly(vinyl-ester).

7. The process of claim 4 , wherein the providing the one or more additional monomers comprises providing unequal portions of the one or more additional monomers.

Assignees

• IBM

Inventors

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

Classifications

• C08G73/0644 Primary

  Poly(1,3,5)triazines · CPC title

• C08F212/28 Primary

  Amines · CPC title

• C08G12/08

  aromatic · CPC title

• C08F12/28

  Amines · CPC title

• C08G73/0638

  with at least three nitrogen atoms in the ring · CPC title