# US 10,118,993 B2 · Systems chemistry approach to polyhexahydrotriazine polymeric structures

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- Number: US 10,118,993 B2
- Document ID: US10118993B2
- Status: Granted
- Kind: B2
- Application number: 15/460,785
- Filed: 2017-03-16
- Published: 2017-06-29
- Granted: 2018-11-06
- Earliest claimed: 2015-11-24
- Assignees: International Business Machines Corporation
- Applicants: International Business Machines Corporation
- Inventors: Dylan J. Boday; Mareva B. Fevre; Jeannette M. Garcia; James L. Hedrick; Rudy J. Wojtecki
- Web page: https://patentgrep.com/patent/US10118993B2

## CPC

- C08G 73/0644: {Poly(1,3,5)triazines}
- C07D 207/452: with hydrocarbon radicals, substituted by hetero atoms, directly attached to the ring nitrogen atom
- C08G 73/065: {Preparatory processes}
- C08G 73/1039: {comprising halogen-containing substituents}
- C08G 73/1064: {containing sulfur}
- C08G 73/1067: {Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound}
- C08L 63/00: Compositions of epoxy resins; Compositions of derivatives of epoxy resins
- C08L 63/04: Epoxynovolacs
- C08L 79/04: Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)

## Abstract

In some embodiments, a product, such as a thermoset, has a polyhexahydrotriazine and a self-polymerized cross-linkable polymer. In some embodiments, a product is the reaction product of a diamine, an aldehyde, and a compound having an α,β-unsaturated electron withdrawing moiety.

## Claims

### Claim 1

A product that is the reaction product of:
a diamine;
an aldehyde; and
a compound having an α,β-unsaturated electron withdrawing moiety.

### Claim 2 (depends on 1)

The product of claim 1, wherein the aldehyde is paraformaldehyde.

### Claim 3 (depends on 1)

The product of claim 1, wherein the compound having an α,β-unsaturated electron withdrawing moiety is
wherein R is selected from the group consisting of ether, aryl, and alkyl.

### Claim 4 (depends on 3)

The product of claim 3, wherein the ether is
the aryl is
and the alkyl is

### Claim 5 (depends on 1)

The product of claim 1, wherein the diamine is of the structure: NH2—X—NH2, wherein X is selected from the group consisting of a phosphine derivative, an ether, and a lactone.

### Claim 6 (depends on 5)

The product of claim 5, wherein the phosphine derivative is
the ether is
and the lactone is

### Claim 7 (depends on 1)

The product of claim 1, wherein the product comprises a polyhexahydrotriazine including the structure:
wherein each instance of X is independently a phosphine derivative, ether, or lactone.

### Claim 8 (depends on 7)

The product of claim 7, wherein the product further comprises: the structure
wherein R is selected from the group consisting of an ether, an aryl group, and an alkyl group, wherein X is selected from the group consisting of a phosphine, an ether, and a lactone, and wherein n is a positive integer.

### Claim 9 (depends on 8)

The composition of claim 8, wherein R is selected from the group consisting of ether of structure
aryl of structure
and alkyl of structure:

### Claim 10 (depends on 9)

The composition of claim 9, wherein n is a positive integer from between about 2 to about 500.

### Claim 11 (depends on 8)

The composition of claim 8, wherein R is ether.

### Claim 12 (depends on 8)

The composition of claim 8, wherein R is aryl.

### Claim 13 (depends on 8)

The composition of claim 8, wherein R is alkyl.

### Claim 14 (depends on 7)

The product of claim 7, wherein the product further comprises: the structure
wherein R is selected from the group consisting of ether, aryl, and alkyl, and wherein n is a positive integer.

### Claim 15 (depends on 14)

The composition of claim 14, wherein R is selected from the group consisting of ether of structure
aryl of structure
and alkyl of structure:

### Claim 16 (depends on 15)

The composition of claim 15, wherein n is a positive integer from between about 2 to about 500.

### Claim 17 (depends on 14)

The composition of claim 14, wherein R is ether.

### Claim 18 (depends on 14)

The composition of claim 14, wherein R is aryl.

### Claim 19 (depends on 14)

The composition of claim 14, wherein R is alkyl.

### Claim 20 (depends on 1)

The product of claim 1, wherein the product comprises: the structure
wherein R is selected from the group consisting of an ether, an aryl group, and an alkyl group, wherein X is selected from the group consisting of a phosphine, an ether, and a lactone, and wherein n is a positive integer.