IP Library Granted Patent US 9,428,445
Granted Patent B2
US 9,428,445 · App. 14/406,920 · Granted Aug 30, 2016

Amine compounds and their use as zero or low VOC neutralizers

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Quick Facts
Patent No.
US 9,428,445
App. No.
14/406,920
Granted
Aug 30, 2016
Kind
B2
Abstract

Provided are compounds for use as neutralizing agents in aqueous formulations. The compounds are of the formula I: (Formula I should be inserted here.) wherein R, R 1 , R 2 , R 3 , R 4 , and R 5 are as defined herein.

Claims (15)

1. A compound of formula I:

or a salt or zwitterion thereof,

wherein R and R 1 are each H;

R 4 is H or linear or branched C 1 -C 3 alkyl;

R 2 and R 3 are independently linear or branched C 1 -C 6 alkyl, or R 2 , R 3 , together with the carbon to which they are attached, form C 3 -C 8 cycloalkyl; and

R 5 is H or linear or branched C 1 -C 6 alkyl optionally substituted with: OH, C(═O)OH, C(═O)NH 2 , SH, CH 3 S, HOOCCH(NH 2 )CH 2 S—S—CH 2 —, phenyl, hydroxyphenyl, imidazolyl, or indoyl; or

R 4 and R 5 , together with the atoms to which they are attached, form a pyrrolidine ring optionally substituted with OH.

2. The compound of claim 1 wherein R 5 is H.

3. The compound of claim 1 wherein R 5 is unsubstituted linear or branched C 1 -C 6 alkyl.

4. The compound of claim 1 wherein R 5 is linear or branched C 1 -C 6 alkyl substituted with OH or C(═O)OH.

5. The compound of claim 1 that is: N-[2-(amino)-2-methylpropyl]-glycine; 2-((2-amino-2-methylpropyl)amino)propanoic acid; 2-((2-amino-2-methylpropyl)amino)-3-methylbutanoic acid; 2-((2-amino-2-methylpropyl)amino)-4-methylpentanoic acid; 2-((2-amino-2-methylpropyl)amino)-3-hydroxypropanoic acid; 2-((2-amino-2-methylpropyl)amino)-3-hydroxybutanoic acid; 2-((2-amino-2-methylpropyl)amino)succinic acid; or 2-((2-amino-2-methylpropyl)amino)pentanedioic acid.

6. A method for neutralizing an aqueous formulation identified as in need of neutralization, the method comprising using, as a neutralizing agent in the formulation, the compound of claim 1 .

7. The method of claim 6 wherein the formulation is an aqueous based paint or coating, or a cleaning product.

8. An aqueous based paint or coating comprising a neutralizing agent, a binder, a carrier, and an optional pigment, wherein the neutralizing agent is a compound of claim 1 .

9. A cleaning formulation comprising a neutralizing agent, a surfactant, and water, wherein the neutralizing agent is a compound of claim 1 .

Assignments (6)
CHANGE OF NAME Recorded Feb 27, 2024
From: ANGUS CHEMICAL COMPANY
To: ADVANCION CORPORATION
Reel/Frame 066697/0518 →
PATENT SECURITY AGREEMENT (1ST LIEN) Recorded Dec 1, 2020
From: ANGUS CHEMICAL COMPANY
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 054553/0706 →
PATENT SECURITY AGREEMENT (2ND LIEN) Recorded Dec 1, 2020
From: ANGUS CHEMICAL COMPANY
To: JEFFERIES FINANCE LLC, AS COLLATERAL AGENT
Reel/Frame 054553/0719 →
RELEASE OF SECURITY INTEREST Recorded Nov 24, 2020
From: JPMORGAN CHASE BANK, N.A.
To: ANGUS CHEMICAL COMPANY
Reel/Frame 054462/0821 →
SUPPLEMENTAL SECURITY AGREEMENT Recorded Jun 10, 2016
From: ANGUS CHEMICAL COMPANY
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 038950/0373 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 13, 2015
From: COBURN, CHARLES E.; MILES, WILLIAM C.
To: ANGUS CHEMICAL COMPANY
Reel/Frame 035162/0847 →