# US 10,370,508 B1 · High temperature chemical compositions and composites produced therefrom

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- Number: US 10,370,508 B1
- Document ID: US10370508B1
- Status: Granted
- Kind: B1
- Application number: 15/635,794
- Filed: 2017-06-28
- Granted: 2019-08-06
- Earliest claimed: 2016-06-28
- Assignees: Jalapeno Holdings, LLC
- Applicants: Jalapeno Holdings, LLC
- Inventors: Richard D. Hreha; Joel P. Brubaker; Patrick J. Hood
- Web page: https://patentgrep.com/patent/US10370508B1

## CPC

- C08J 5/042: {with carbon fibres}
- C08G 73/02: Polyamines
- C08G 73/0273: {Polyamines containing heterocyclic moieties in the main chain}
- C08G 73/0611: {with only one nitrogen atom in the ring, e.g. polypyrroles (polysuccinimides C08G73/1092)}
- C08G 73/0672: {with only one nitrogen atom in the ring}
- C08J 5/04: Reinforcing macromolecular compounds with loose or coherent fibrous material
- C08J 2379/02: Polyamines
- C08J: WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H (working, e.g. shaping, of plastics B29)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS

## Abstract

Chemical compositions are provided that include at least one of Formula I or Formula II: where n and m are integers, at least one of R1 or R2 comprises an aromatic moiety, and X is selected from the group consisting of CH2, NH, O, S, SO2, and combinations thereof. Composites formed from the chemical composition and at least one reinforcement material are also provided.

## Claims

### Claim 1

A chemical composition comprising at least one of Formula I or Formula II:
wherein:
where n and m are each an integer greater than or equal to 1,
at least one of R1 or R2 comprises an aromatic moiety, and
X is selected from the group consisting of CH2, NH, O, S, SO2, and combinations thereof.

### Claim 2 (depends on 1)

The chemical composition of claim 1, wherein X is selected from the group consisting of CH2, NH, O, S, and combinations thereof.

### Claim 3 (depends on 1)

The chemical composition of claim 1, wherein n, m, or both, are integers from 1 to 200.

### Claim 4 (depends on 1)

The chemical composition of claim 1, wherein R1, R2, or both comprise one or more of a phenyl group, a naphthyl group, a benzyl group, or a 4-cyanophenyl group.

### Claim 5 (depends on 1)

The chemical composition of claim 1, wherein R1, R2, or both comprise one or more of an ether group, a sulfur group, a sulfonyl group, an imine group, an amide group, a methylene group, a dialkyl methylene group, an isopropyl group, a trifluoromethyl group, a hexafluoroisopropyl group, a carbonyl group, a methyl group, a propyl group, a dimethylamino group, or a boronic acid group.

### Claim 6 (depends on 1)

The chemical composition of claim 1, wherein R1, R2, or both comprise one or more of an (1-(5-(1-(5-Formyl-2-furfyl)-1-methylethyl)-2-furfyl)-1-methylethyl), diphenylsulfone, diphenyl sulfone, diphenyl ether, 1,3-bis(phenoxy)-benzene, moiety, 4,4′-(1,3-phenylenedioxy)dianiline, 1,3-bis(3-aminophenoxy)benzene, 4,4′-oxydianiline, 4-aminophenyl sulfone, 3-aminophenyl sulfone, or isophthalaldehyde derivatives.

### Claim 7 (depends on 1)

The chemical composition of claim 1, wherein the composition is used in one or more of the architecture, coating, composite, construction, oil and gas, mining, defense, space, aerospace, automotive, marine, or electronic industries.

### Claim 8 (depends on 1)

A composite comprising the chemical composition of claim 1 and at least one reinforcement material.

### Claim 9 (depends on 8)

The composite of claim 8, wherein the reinforcement material comprises one or more of carbon fiber, glass fiber, aramid fiber, polymer fiber, felt material, carbon felt, aerogel, syntactic material, random fiber mats, scrims, chopped fibers, fiber knits, unidirectional fiber plies, three-dimensional fiber weaves, three-dimensional fiber preforms, plain weave fabrics, twill fabrics, harness satin fabrics or combinations thereof.

### Claim 10 (depends on 8)

The composite of claim 8, wherein the composite is an article used in at least one of an architecture, coating, composite, construction, oil and gas, mining, defense, space, aerospace, automotive, marine, or electronic industries.

### Claim 11 (depends on 1)

The chemical composition of claim 1, wherein X is O.

### Claim 12 (depends on 1)

The chemical composition of claim 1, wherein X is NH.

### Claim 13 (depends on 1)

The chemical composition of claim 1, wherein R1, R2, or both comprise a phenyl group.

### Claim 14 (depends on 1)

The chemical composition of claim 1, wherein R1, R2, or both comprise a naphthyl group.

### Claim 15 (depends on 1)

The chemical composition of claim 1, wherein R1, R2, or both comprise one or more of an ether group, an imine group, an amide group, a hexafluoroisopropyl group, or an isopropyl group.

### Claim 16 (depends on 1)

The chemical composition of claim 1, wherein R1, R2, or both comprise a diphenyl ether moiety.

### Claim 17 (depends on 1)

The chemical composition of claim 1, wherein R1, R2, or both comprise an isophthalaldehyde derivative.

### Claim 18 (depends on 8)

The composite of claim 8, wherein the reinforcement material comprises one or more of carbon fiber, glass fiber, three-dimensional fiber preforms, or combinations thereof.