Sterically bulky stabilizers
View Patent ↗A sterically bulky stabilizer that includes an alkylated-benzimidazolone compound, where the sterically bulky stabilizer is associated non-covalently with a benzimidazolone pigment, and the presence of the sterically bulky stabilizer limits the extent of particle growth and aggregation, to afford nanoscale pigment particles.
1. A sterically bulky stabilizer of the formula:
wherein each of R a and R b independently represent H or substituted or unsubstituted alkyl groups, provided that at least one of R a and R b on each benzimidazolone group represents H, and R c represents a group selected from the group consisting of:
—X—(CH 2 ) n X—; —[(XCH 2 CH 2 ) n ]X—; —[(C═O)—(CH 2 ) n — (C═O)]—; —X—[(C═O)—(CH 2 ) n —(C═O)]—X—; —X—[(C═O)—X—(CH 2 ) n —X—(C═O)]—X—; —[(C═O)—X—(CH 2 ) n —X—(C═O)]—;
wherein X, X 1 , and X 2 independently represent O, S, or NH, and n is an integer of 1 to 50.
2. The sterically bulky stabilizer of claim 1 , wherein the sterically bulky stabilizer compound comprises an alkylated-benzimidazolone selected from the group consisting of the following compounds:
Group X
R 1
R 2
R 3
X 1 = X 2 = NH
H
H
X 1 = O X 2 = NH
H
H
X 1 = NH
H
H
X 1 = O
H
H
X 1 = O
H
H
X 1 = NH
H
H
3. A sterically bulky stabilizer comprising an alkylated-benzimidazolone selected from the group consisting of the following compounds:
Position 5
functional
Sterically Bulky Group(s)
moiety
X
R 1
R 2
R 3
NH
(CH 2 ) n CH 3 n = 2, 11, 17
—
—
NH
—
—
NH
—
—
NH
—
—
X 1 = X 2 = NH
(CH 2 ) n CH 3 n = 11, 17
—
—
X 1 = O X 2 = NH
(CH 2 ) n CH 3 n = 11, 17
—
—
N
H
(CH 2 ) n CH 3 n = 1, 17
—
N
H
—
N
(CH 2 ) n CH 3 n = 3, 11, 17
(CH 2 ) n CH 3 n = 3, 11, 17
—
N
—
N
—
N
(CH 2 ) n CH 3 n = 1, 17
(CH 2 ) n CH 3 n = 1, 17
(CH 2 ) n CH 3 n = 1, 17
N
N
Position 5
functional
moiety
R 1
R 2
R 3
X 1 = X 2 = NH
H
H
X 1 = O X 2 = NH
H
H
X 1 = NH
H
H
X 1 = O
H
H
X 1 = O
H
H
X 1 = NH
H
H
—
H
—(CH 2 ) n CH 3 n = 1, 17
—
—
—(CH 2 ) n CH 3 n = 1, 17
H
—
—
H
H
—
—
H
H
—
Group X
R c
wherein DC n represents a diazo moiety.