IP Library › Granted Patent US 8,426,636
Granted Patent B2
US 8,426,636 · App. 13/189,887 · Granted Apr 23, 2013

Sterically bulky stabilizers

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Quick Facts
Patent No.
US 8,426,636
App. No.
13/189,887
Granted
Apr 23, 2013
Kind
B2
Abstract

A sterically bulky stabilizer that is associated non-covalently with a benzimidazolone pigment. The sterically bulky stabilizer compound includes an aromatic acid derivative, and the presence of the sterically bulky stabilizer limits an extent of particle growth and aggregation, to afford nanoscale pigment particles.

Claims (686)

1. A sterically bulky stabilizer of the formula:

wherein R 1 to R 6 can be the same or different and represent H, —NH—(C═O)—R′, —(C═O)—NH—R′, —NH—R′, —NH—(C═O)—NH—R′, —O—(C═O)—R′, branched or linear alkyleneoxy chains, or —OR′, wherein R′ is predominantly a linear or branched alkyl or cycloaliphatic group that may contain heteroatoms within the alkyl groups,

provided that at least one of R 1 to R 6 represents —COOH or —CONH 2 , at least one of R 1 to R 6 is hydrogen, and at least one of R 1 to R 6 represents a sterically bulky group comprising a moiety selected from the group consisting of:

2. The sterically bulky stabilizer of claim 1 , wherein the sterically bulky stabilizer is amphiphilic.

3. A sterically bulky stabilizer of the formula:

where at least one of R 1 to R 6 represents —COOH or —CONH 2 , and at least one of R 1 to R 6 is hydrogen, and R y is a bridging group selected from the group consisting of —(CH 2 ) n ; —X—(CH 2 ) n X; —[(XCH 2 CH 2 ) n ]X—; —[(C═O)—(CH 2 ) n —(C═O)]; —X—[(C═O)—X—(CH 2 ) n —X—(C═O)]—X—;

wherein X, X 1 , and X 2 independently represent O, S, or NH, and n is an integer of 1 to 50.

4. A sterically bulky stabilizer compound comprising an alkylated derivative of an aromatic acid, selected from the group consisting of the following compounds:

R 1

R 2

R 3

R 5

—COOH

H

—COOH

H

—COOH

H

—COOH

H

—COOH

H

—COOH

H

—COOH

H

—COOH

H

—COOH

H

—COOH

H

—COOH

H

—COOH

H

—COOH

H

—COOH

H

—COOH

H

—COOH

H

—COOH

H

—COOH

H

—COOH

H

—COOH

H

—CONH 2

H

—CONH 2

H

—CONH 2

H

—CONH 2

H

—CONH 2

H

—CONH 2

H

—CONH 2

H

—CONH 2

H

—CONH 2

H

—CONH 2

H

—CONH 2

H

—CONH 2

H

—CONH 2

H

—CONH 2

H

—CONH 2

H

—CONH 2

H

—CONH 2

H

—CONH 2

H

—CONH 2

H

—CONH 2

H

—CONH 2

H

—COOH

H

—COOH

—COOH

H

—COOH

—COOH

H

—COOH

—COOH

H

—COOH

—COOH

H

—COOH

—COOH

H

—COOH

—COOH

H

—COOH

—COOH

H

—COOH

—COOH

H

—COOH

—COOH

H

—COOH

—COOH

H

—COOH

—COOH

H

—COOH

—COOH

H

—COOH

—COOH

H

—COOH

—COOH

H

—COOH

—COOH

H

—COOH

—COOH

H

—COOH

—COOH

H

—COOH

—COOH

H

—COOH

—CONH 2

H

—CONH 2

—CONH 2

H

—CONH 2

—CONH 2

H

—CONH 2

—CONH 2

H

—CONH 2

—CONH 2

H

—CONH 2

—CONH 2

H

—CONH 2

—CONH 2

H

—CONH 2

—CONH 2

H

—CONH 2

—CONH 2

H

—CONH 2

—CONH 2

H

—CONH 2

—CONH 2

H

—CONH 2

—CONH 2

H

—CONH 2

—CONH 2

H

—CONH 2

—CONH 2

H

—CONH 2

—CONH 2

H

—CONH 2

—CONH 2

H

—CONH 2

—CONH 2

H

—CONH 2

—CONH 2

H

—CONH 2

—CONH 2

H

—CONH 2

—CONH 2

H

—CONH 2

—COOH

—COOH

H

—COOH

—COOH

H

—COOH

—COOH

H

—COOH

—COOH

H

—COOH

—COOH

H

—COOH

—COOH

H

—COOH

—COOH

H

—COOH

—COOH

H

H

—COOH

—COOH

H

—COOH

—COOH

H

—COOH

—COOH

H

—COOH

—COOH

H

—COOH

—COOH

H

—COOH

—COOH

H

—COOH

—COOH

H

—COOH

—COOH

H

—COOH

—COOH

H

—COOH

—COOH

H

—COOH

—COOH

H

—COOH

—COOH

H

—COOH

—COOH

H

—COOH

—COOH

H

—COOH

—COOH

H

—COOH

—COOH

H

—COOH

—COOH

H

—COOH

—COOH

H

—COOH

—COOH

H

—COOH

—COOH

H

—COOH

—COOH

H

—CONH 2

—CONH 2

H

—CONH 2

—CONH 2

H

—CONH 2

—CONH 2

H

—CONH 2

—CONH 2

H

—CONH 2

—CONH 2

H

—CONH 2

—CONH 2

H

—CONH 2

—CONH 2

H

—CONH 2

—CONH 2

H

—CONH 2

—CONH 2

H

—CONH 2

—CONH 2

H

—CONH 2

—CONH 2

H

—CONH 2

—CONH 2

H

—CONH 2

—CONH 2

H

—CONH 2

—CONH 2

H

—CONH 2

—CONH 2

H

—CONH 2

—CONH 2

H

—CONH 2

—CONH 2

H

—CONH 2

—CONH 2

H

—CONH 2

—CONH 2

H

—CONH 2

—CONH 2

H

—CONH 2

—CONH 2

R 1

R 2

R 3

R 4

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

R y

R 1

R 2

R 3

R 4

R 5

X = NH

H

—COOH

H

—COOH

H

X = O

H

—COOH

H

—COOH

H

X = NH

H

—COOH

H

—COOH

H

X = O

H

—COOH

H

—COOH

H

X 1 = X 2 = NH

H

—COOH

H

—COOH

H

X 1 = O, X 2 = NH

H

—COOH

H

—COOH

H

X = NH

H

—CONH 2

H

—CONH 2

H

X = O

H

—CONH 2

H

—CONH 2

H

X = NH

H

—CONH 2

H

—CONH 2

H

X = O

H

—CONH 2

H

—CONH 2

H

X 1 = X 2 = NH

H

—CONH 2

H

—CONH 2

H

X 1 = O, X 2 = NH

H

—CONH 2

H

—CONH 2

H

X = NH

H

—COOH

—COOH

H

H

X = O

H

—COOH

—COOH

H

H

X = NH

H

—COOH

—COOH

H

H

X = O

H

—COOH

—COOH

H

H

X 1 = X 2 = NH

H

—COOH

—COOH

H

H

X 1 = O, X 2 = NH

H

—COOH

—COOH

H

H

X = NH

H

H

—COOH

H

H

X = O

H

H

—COOH

H

H

X = NH

H

H

—COOH

H

H

X = O

H

H

—COOH

H

H

X 1 = X 2 = NH

H

H

—COOH

H

H

X 1 = O, X 2 = NH

H

H

—COOH

H

H

X = NH

H

H

—CONH 2

H

H

X = O

H

H

—CONH 2

H

H

X = NH

H

H

—CONH 2

H

H

X = O

H

H

—CONH 2

H

H

X 1 = X 2 = NH

H

H

—CONH 2

H

H

X 1 = O, X 2 = NH

H

H

—CONH 2

H

H

X = NH

—COOH

H

H

—COOH

H

X = O

—COOH

H

H

—COOH

H

X = NH

—COOH

H

H

—COOH

H

X = O

—COOH

H

H

—COOH

H

X 1 = X 2 = NH

—COOH

H

H

—COOH

H

X 1 = O, X 2 = NH

—COOH

H

H

—COOH

H

X = NH

—CONH 2

H

H

—CONH 2

H

X = O

—CONH 2

H

H

—CONH 2

H

X = NH

—CONH 2

H

H

—CONH 2

H

X = O

—CONH 2

H

H

—CONH 2

H

X 1 = X 2 = NH

—CONH 2

H

H

—CONH 2

H

X 1 = O, X 2 = NH

—CONH 2

H

H

—CONH 2

H.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 14, 2025
From: XEROX CORPORATION
To: GENESEE VALLEY INNOVATIONS, LLC
Reel/Frame 073562/0677 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 1, 2017
From: NATIONAL RESEARCH COUNCIL OF CANADA
To: XEROX CORPORATION
Reel/Frame 042195/0428 →