# US 11,028,194 B1 · Bis-Schiff base compositions and formulations

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- Number: US 11,028,194 B1
- Document ID: US11028194B1
- Status: Granted
- Kind: B1
- Application number: 16/662,642
- Filed: 2019-10-24
- Granted: 2021-06-08
- 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/US11028194B1

## CPC

- C08F 34/02: in a ring containing oxygen (coumarone-indene polymers C08F244/00)
- C07D 307/52: Radicals substituted by nitrogen atoms not forming part of a nitro radical
- C09D 4/00: Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond {; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16}
- C09D 7/20: Diluents or solvents
- C09D 145/00: Coating compositions based on homopolymers or copolymers of compounds having no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic or in a heterocyclic system; Coating compositions based on derivatives of such polymers (based on polymers of cyclic esters of polyfunctional acids C09D131/00; based on polymers of cyclic anhydrides or imides C09D135/00)
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)

## 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 a chemical having the structure of Formula (I):
wherein:
R is selected from at least one of Formula (IV), Formula (V), Formula (VI), Formula (VII), 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), Formula (XXVI), Formula (XXVII), Formula (XXVIII), Formula (XXIX), Formula (XXX), or Formula (XXXI);
X comprises an aromatic moiety, an aliphatic moiety, or a hydrogen when R is selected from Formula (VI), Formula (VII), Formula (VIII), Formula (XII), Formula (XIII), Formula (XIV), Formula (XV), Formula (XVI), Formula (XIX), Formula (XX), Formula (XXII), Formula (XXIII), Formula (XXIV), Formula (XXV), Formula (XXVI), Formula (XXVII), Formula (XXVIII), Formula (XXIX), Formula (XXX), or Formula (XXXI);
X consists of a hydrogen when R is selected from Formula (IV), Formula (V), Formula (IX), Formula (X), Formula (XI), or Formula (XVII);
X′ comprises an aromatic moiety, an aliphatic moiety, or a hydrogen when R is selected from Formula (VI), Formula (VII), Formula (VIII), Formula (XII), Formula (XIII), Formula (XIV), Formula (XV), Formula (XVI), Formula (XIX), Formula (XX), Formula (XXII), Formula (XXIII), Formula (XXIV), Formula (XXV), Formula (XXVI), Formula (XXVII), Formula (XXVIII), Formula (XXIX), Formula (XXX), or Formula (XXXI); and
X′ consists of a hydrogen when R is selected from Formula (IV), Formula (V), Formula (IX), Formula (X), Formula (XI), or Formula (XVII):
wherein for Formula (XXV), Formula (XXVI), Formula (XXVII), Formula (XXVIII), Formula (XXIX), Formula (XXX), or Formula (XXXI):
R1, R2, R3, R4, R5, R6, R7, and R8 are each independently selected from 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 (XXI), Formula (XXII), Formula (XXIII), and Formula (XXIV),
the aromatic moieties Ar1, Ar2, Ar3, Ar4, Ar5, Ar6, and Ar7 are meta-substituted or para-substituted; and
Formula (XXVIII), Formula (XXIX), Formula (XXX), and Formula (XXXI) are each illustrated broken across multiple lines but represent a single continuous structure.

### 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 500 cP at less than or equal to 150° C., as measured by rotational rheometry.

### Claim 3 (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 4 (depends on 3)

The chemical composition of claim 3, wherein the chemical composition is used as a thermosetting resin in the composite industry.

### Claim 5 (depends on 3)

The chemical composition of claim 3, wherein the chemical composition is used as a thermosetting resin in the coating industry.

### Claim 6 (depends on 1)

A polymer produced from the chemical composition of claim 1.

### Claim 7 (depends on 6)

The polymer of claim 6, wherein the polymer is used in at least one of an architecture, coating, construction, oil and gas, mining, defense, space, aerospace, automotive, marine, manufacturing, or electronic industries.

### Claim 8 (depends on 6)

The polymer of claim 6, wherein the polymer is used as a thermosetting resin in the composite industry.

### Claim 9 (depends on 6)

The polymer of claim 6, wherein the polymer is used as a thermosetting resin in the coating industry.

### Claim 10

A chemical formulation comprising:
at least one solvent; and
a chemical having the structure of Formula (I):
wherein:
R is selected from at least one of Formula (IV), Formula (V), Formula (VI), Formula (VII), 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), Formula (XXVI), Formula (XXVII), Formula (XXVIII), Formula (XXIX), Formula (XXX), or Formula (XXXI);
X comprises an aromatic moiety, an aliphatic moiety, or a hydrogen when R is selected from Formula (VI), Formula (VII), Formula (VIII), Formula (XII), Formula (XIII), Formula (XIV), Formula (XV), Formula (XVI), Formula (XIX), Formula (XX), Formula (XXII), Formula (XXIII), Formula (XXIV), Formula (XXV), Formula (XXVI), Formula (XXVII), Formula (XXVIII), Formula (XXIX), Formula (XXX), or Formula (XXXI);
X consists of a hydrogen when R is selected from Formula (IV), Formula (V), Formula (IX), Formula (X), Formula (XI), or Formula (XVII);
X′ comprises an aromatic moiety, an aliphatic moiety, or a hydrogen when R is selected from Formula (VI), Formula (VII), Formula (VIII), Formula (XII), Formula (XIII), Formula (XIV), Formula (XV), Formula (XVI), Formula (XIX), Formula (XX), Formula (XXII), Formula (XXIII), Formula (XXIV), Formula (XXV), Formula (XXVI), Formula (XXVII), Formula (XXVIII), Formula (XXIX), Formula (XXX), or Formula (XXXI); and
X′ consists of a hydrogen when R is selected from Formula (IV), Formula (V), Formula (IX), Formula (X), Formula (XI), or Formula (XVII):
wherein for Formula (XXV), Formula (XXVI), Formula (XXVII), Formula (XXVIII), Formula (XXIX), Formula (XXX), or Formula (XXXI):
R1, R2, R3, R4, R5, R6, R7, and R8 are each independently selected from 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 (XXI), Formula (XXII), Formula (XXIII), and Formula (XXIV), the aromatic moieties Ar1, Ar2, Ar3, Ar4, Ar5, Ar6, and Ar7 are meta-substituted or para-substituted; and
Formula (XXVIII), Formula (XXIX), Formula (XXX), and Formula (XXXI) are each illustrated broken across multiple lines but represent a single continuous structure.

### Claim 11 (depends on 10)

The chemical formulation of claim 10, 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 12 (depends on 10)

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

### Claim 13 (depends on 10)

The chemical formulation of claim 10, wherein the chemical composition contains from 40 wt % to 85 wt % of the chemical having the structure of Formula (I).

### Claim 14 (depends on 10)

The chemical formulation of claim 10, 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.