IP Library Granted Patent US 10,501,578
Granted Patent B1
US 10,501,578 · App. 15/440,829 · Granted Dec 10, 2019

Bis-Schiff base compositions and formulations

Inventors: Richard D. Hreha (Dayton, OH); Tat H. Tong (Bellbrook, OH)
Assignee: Jalapeno Holdings, LLC
C08G73/00C07D307/34
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Quick Facts
Patent No.
US 10,501,578
App. No.
15/440,829
Granted
Dec 10, 2019
Kind
B1
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 (23)

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):

2. 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.

3. 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.

4. 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.

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

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

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):

8. 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.

9. 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).

10. 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).

11. 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.

Assignments (8)
SECURITY INTEREST Recorded Apr 8, 2025
From: SYSTIMA TECHNOLOGIES, INC.
To: CITIBANK, N.A., AS AGENT
Reel/Frame 070775/0023 →
RELEASE OF SECURITY INTEREST Recorded Apr 8, 2025
From: TCW ASSET MANAGEMENT COMPANY, LLC
To: SYSTIMA TECHNOLOGIES, INC.
Reel/Frame 070767/0592 →
SECURITY INTEREST Recorded Sep 30, 2022
From: SYSTIMA TECHNOLOGIES, INC.
To: TCW ASSET MANAGEMENT COMPANY, LLC, AS ADMINISTRATIVE AGENT
Reel/Frame 061276/0116 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 2, 2022
From: CORNERSTONE RESEARCH GROUP, INCORPORATED
To: SYSTIMA TECHNOLOGIES, INC.
Reel/Frame 060694/0679 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 27, 2022
From: CORNERSTONE RESEARCH GROUP, INCORPORATED
To: SYSTIMA TECHNOLOGIES, INC.
Reel/Frame 060318/0876 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 14, 2022
From: JALAPENO HOLDINGS, LLC
To: CORNERSTONE RESEARCH GROUP, INC.
Reel/Frame 059595/0149 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 1, 2019
From: CORNERSTONE RESEARCH GROUP, INC.
To: JALAPENO HOLDINGS, LLC
Reel/Frame 048482/0219 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 27, 2017
From: HREHA, RICHARD D.; TONG, TAT H.
To: CORNERSTONE RESEARCH GROUP, INC.
Reel/Frame 042166/0022 →
Continuity (1)
Provisional Application 62298504 · Feb 23, 2016
Cited By (1)
US 12,359,024