IP Library Granted Patent US 11,572,351
Granted Patent B1
US 11,572,351 · App. 17/332,237 · Granted Feb 7, 2023

Bis-Schiff base compositions and formulations

Inventors: Richard D. Hreha (Dayton, OH); Tat H. Tong (Bellbrook, OH)
Assignee: Systima Technologies, Inc.
C07D307/34
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Quick Facts
Patent No.
US 11,572,351
App. No.
17/332,237
Granted
Feb 7, 2023
Kind
B1
Abstract

A chemical formulation having at least one solvent and a chemical 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.

Claims (16)

1. 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 (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):

R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 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 Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 , Ar 6 , and Ar 7 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, wherein the solvent is selected from the aromatic imines of Formula (XXXIV), Formula (XXXV), Formula (XXXVI), Formula (XXXVII), Formula (XXXVIII), Formula (XXXIX), or Formula (XL):

2. The chemical formulation of claim 1 , wherein the chemical composition contains from 10 wt % to 95 wt % of the chemical having the structure of Formula (I).

3. The chemical formulation of claim 1 , wherein the chemical composition contains from 40 wt % to 85 wt % of the chemical having the structure of Formula (I).

4. The chemical formulation of claim 1 , 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 (10)
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 →
RELEASE OF SECURITY INTEREST Recorded Apr 8, 2025
From: TCW ASSET MANAGEMENT COMPANY, LLC
To: SYSTIMA TECHNOLOGIES, INC.; KARMAN SPACE & DEFENSE LLC
Reel/Frame 070767/0760 →
SECURITY INTEREST Recorded May 28, 2024
From: SYSTIMA TECHNOLOGIES, INC.; KARMAN HOLDINGS LLC
To: TCW ASSET MANAGEMENT COMPANY, LLC, AS ADMINISTRATIVE AGENT
Reel/Frame 067536/0743 →
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 May 27, 2021
From: CORNERSTONE RESEARCH GROUP, INC.
To: JALAPENO HOLDINGS, LLC
Reel/Frame 056373/0785 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 27, 2021
From: HREHA, RICHARD D.; TONG, TAT H.
To: CORNERSTONE RESEARCH GROUP, INC.
Reel/Frame 056373/0687 →
Continuity (3)
Continuation In Part 16662642 · Oct 24, 2019
Continuation In Part 15440829 · Feb 23, 2017
Provisional Application 62298504 · Feb 23, 2016
Cited By (1)
US 12,297,334