Polyhemiaminal and polyhexahydrotriazine materials from 1,4 conjugate addition reactions
AssigneeInternational Business Machines Corporation
InventorsDylan J. Boday, Mareva Fevre, Jeannette M. Garcia, James L. Hedrick, Rudy J. Wojtecki
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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.
Claims20
A polymeric material, comprising:
- a first trivalent hemiaminal group having the structure:
- and
- a first, second, and third phenyl group each having the structure:
- wherein:
- each wavy bond site of the first trivalent hemiaminal group is covalently attached to a respective one of the first, second, and third phenyl groups at a wavy bond site of the respective one of the first, second, and third phenyl groups;
- at least one of B, C, or D on at least one of the first, second, or third phenyl groups has the structure:
- and B, C, and D are hydrogen (H) otherwise;
- at least one of R1 and R2 has the structure:
- and
- R3 includes at least one carbon.
A polymeric material, comprising:
- a first trivalent hemiaminal group having the structure:
- and
- a first, second, and third phenyl group each having the structure:
- wherein:
- each wavy bond site of the first trivalent hemiaminal group is covalently attached to a respective one of the first, second, and third phenyl groups at a wavy bond site of the respective one of the first, second, and third phenyl groups;
- at least one of B, C, or D on at least one of the first, second, or third phenyl groups has the structure:
- and B, C, and D are hydrogen (H) otherwise;
- R1 in at least one instance is hydrogen (H);
- R2 has the structure:
- and
- R3 includes at least one carbon.
A polymeric material, comprising:
- a first trivalent hemiaminal group having the structure:
- and
- a first, second, and third phenyl group each having the structure:
- wherein:
- each wavy bond site of the first trivalent hemiaminal group is covalently attached to a respective one of the first, second, and third phenyl groups at a wavy bond site of the respective one of the first, second, and third phenyl groups;
- at least one of B, C, or D on at least one of the first, second, or third phenyl groups has the structure:
- and B, C, and D are hydrogen (H) otherwise;
- R1 in each instance is hydrogen (H);
- R2 has the structure:
- and
- R3 in at least one instance has the structure:
- wherein R4 comprises a methylene unit, and R5 comprises a second trivalent hemiaminal group.
Dependencies are inferred from the claim text.