Polyhemiaminal and polyhexahydrotriazine materials from 1,4 conjugate addition reactions

Patent metadata

Field	Value
Publication number	US-2016264744-A1
Application number	US-201514885706-A
Country	US
Kind code	A1
Filing date	Oct 16, 2015
Priority date	Mar 10, 2015
Publication date	Sep 15, 2016
Grant date	—

Abstract

Polyhemiaminal (PHA) and polyhexahydrotriazine (PHT) materials are modified by 1,4 conjugate addition chemical reactions to produce a variety of molecular architectures comprising pendant groups and bridging segments. The materials are formed by a method that includes heating a mixture comprising solvent(s), paraformaldehyde, aromatic amine groups, aliphatic amine Michael donors, and Michael acceptors, such as acrylates. The reaction mixtures may be used to prepare polymer pre-impregnated materials and composites containing PHT matrix resin.

First claim

1 . A method of producing a composite article, comprising:
forming a mixture comprising a solvent, paraformaldehyde, an aromatic amine, a Michael addition donor, and a Michael addition acceptor; heating the mixture to a first temperature to produce a mixture of a first viscosity; coating a work piece with the mixture of the first viscosity to produce a prepreg; heating the prepreg to a second temperature to produce a B-stage prepreg of a second viscosity; cooling the B-stage prepreg; forming an article from the B-stage prepreg; and heating the article at a temperature from about 150° C. to about 280° C. to form a cured composite containing polyhexahydrotriazine.

2 . The method of claim 1 , wherein the mixture of the first viscosity is produced at a temperature from about 20° C. to about 40° C.

3 . The method of claim 1 , wherein the mixture of the first viscosity comprises covalently bonded Michael addition reaction products.

4 . The method of claim 1 , wherein the mixture of the first viscosity comprises covalently bonded Michael addition reaction products and PHA oligomers or polymers.

5 . The method of claim 2 , wherein the second temperature is about 40° C. to about 145° C.

6 . The method of claim 5 , wherein the B-stage prepreg of the second viscosity comprises covalently bonded Michael addition reaction products and PHA oligomers or polymers.

7 . The method of claim 1 , wherein the composite article comprises at least an interpenetrating polymer network comprising two or more polymers.

Assignees

• IBM

Inventors

• Boday Dylan J
• Fevre Mareva
• Garcia Jeannette M
• Hedrick James L
• Wojtecki Rudy J

Classifications

• C08G73/0273 Primary

  Polyamines containing heterocyclic moieties in the main chain · CPC title

• C08J5/24 Primary

  Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs · CPC title

• C08J2361/22

  of aldehydes with acyclic or carbocyclic compounds · CPC title

• C09D161/22

  of aldehydes with acyclic or carbocyclic compounds · CPC title

• C08G73/0638

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