# US 10,501,578 B1 · Bis-Schiff base compositions and formulations

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- Number: US 10,501,578 B1
- Document ID: US10501578B1
- Status: Granted
- Kind: B1
- Application number: 15/440,829
- Filed: 2017-02-23
- Granted: 2019-12-10
- Earliest claimed: 2016-02-23
- Assignees: Jalapeno Holdings, LLC
- Applicants: Jalapeno Holdings, LLC
- Inventors: Richard D. Hreha; Tat H. Tong
- Web page: https://patentgrep.com/patent/US10501578B1

## CPC

- C08G 73/00: Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00 {(polycarbodiimides prepared from isocyanates C08G18/025, C08G18/797)}
- C07D 307/34: having two or three double bonds between ring members or between ring members and non-ring members
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

Chemical compositions are provided having the structure of Formula (I): where R includes at least one aromatic moiety, and X and X′ may both or independently include an aromatic moiety, an aliphatic moiety, or a hydrogen. Additionally, chemical formulations are provided which include the chemical composition having the structure of Formula (I) and at least one solvent.

## Claims

### Claim 1

A chemical composition comprising the structure of Formula (I):
wherein:
X consists of a hydrogen;
R is selected from at least one of Formula (IV), Formula (V), Formula (VI), Formula (VII), Formula (VIII), Formula (IX), Formula (X), Formula (XI), Formula (XII), Formula (XIII), Formula (XIV), Formula (XV), Formula (XVI), Formula (XVII), Formula (XVIII), Formula (XIX), Formula (XX), Formula (XXII), Formula (XXIII), Formula (XXIV), Formula (XXV), or Formula (XXVI);
X′ comprises an aromatic moiety, an aliphatic moiety, or a hydrogen when R is selected from Formula (IV), Formula (V), Formula (VI), Formula (VII), Formula (VIII), Formula (XII), Formula (XIII), Formula (XIV), Formula (XV), Formula (XVI), Formula (XVII), Formula (XVIII), Formula (XIX), Formula (XX), Formula (XXII), Formula (XXIII), Formula (XXIV), Formula (XXV), or Formula (XXVI); and
X′ consists of a hydrogen when R is selected from Formula (IX), Formula (X), or Formula (XI):

### Claim 2 (depends on 1)

The chemical composition of claim 1, wherein the chemical composition has a melt viscosity of less than or equal to 100,000 centipoises (cP) at less than or equal to 150° C., as measured by rotation rheometry.

### Claim 3 (depends on 1)

The chemical composition of claim 1, wherein the chemical composition has a melt viscosity of less than or equal to 500 cP at less than or equal to 150° C., as measured by rotational rheometry.

### Claim 4 (depends on 1)

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

### Claim 5 (depends on 4)

The chemical composition of claim 4, wherein the chemical composition is used as a thermosetting resin in the composite industry.

### Claim 6 (depends on 4)

The chemical composition of claim 4, wherein the chemical composition is used as a thermosetting resin in the coating industry.

### Claim 7

A chemical formulation comprising:
at least one solvent; and
a component having the structure of Formula (I):
wherein:
X consists of a hydrogen;
R is selected from at least one of Formula (IV), Formula (V), Formula (VI), Formula (VII), Formula (VIII), Formula (IX), Formula (X), Formula (XI), Formula (XII), Formula (XIII), Formula (XIV), Formula (XV), Formula (XVI), Formula (XVII), Formula (XVIII), Formula (XIX), Formula (XX), Formula (XXII), Formula (XXIII), Formula (XXIV), Formula (XXV), or Formula (XXVI);
X′ comprises an aromatic moiety, an aliphatic moiety, or a hydrogen when R is selected from Formula (IV), Formula (V), Formula (VI), Formula (VII), Formula (VIII), Formula (XII), Formula (XIII), Formula (XIV), Formula (XV), Formula (XVI), Formula (XVII), Formula (XVIII), Formula (XIX), Formula (XX), Formula (XXII), Formula (XXIII), Formula (XXIV), Formula (XXV), or Formula (XXVI); and
X′ consists of a hydrogen when R is selected from Formula (IX), Formula (X), or Formula (XI):

### Claim 8 (depends on 7)

The chemical formulation of claim 7, wherein the solvent is selected from the group consisting of toluene, dichloromethane, chloroform, acetone, tetrahydrofuran, cyclopentanone, parachlorobenzotrifluoride, dibasic ester, N-methylpyrrolidine, and combinations thereof.

### Claim 9 (depends on 7)

The chemical formulation of claim 7, wherein the chemical composition contains from 10 wt % to 90 wt % of the component having the structure of Formula (I).

### Claim 10 (depends on 8)

The chemical formulation of claim 8, wherein the chemical composition contains from 40 wt % to 85 wt % of the component having the structure of Formula (I).

### Claim 11 (depends on 7)

The chemical formulation of claim 7, wherein the formulation is used in at least one of an architecture, coating, construction, oil and gas, mining, defense, space, aerospace, automotive, marine, manufacturing, or electronic industries.