Nanosized particles of benzimidazolone pigments
View Patent ↗A nanoscale pigment particle composition includes an organic benzimidazolone pigment, and a sterically bulky stabilizer compound, wherein the benzimidazolone pigment associates non-covalently with the sterically bulky stabilizer compound that is a substituted pyridine derivative; and the presence of the associated stabilizer limits the extent of particle growth and aggregation, to afford nanoscale pigment particles.
1. A sterically bulky stabilizer of the formula:
where X represents —O—, and R 1 and R 2 are different and independently represent a linear or branched alkyl or cycloaliphatic group, and which may contain heteroatoms.
2. A sterically bulky stabilizer of the formula:
where X represents —N(H)— or —O—, and R 2 are different and independently selected from the group consisting of
wherein m and n independently represent an integer of 0 to about 30.
3. A sterically bulky stabilizer compound of the formula:
where:
R 1 to R 4 can be the same or different and represent H, —NH—(C═O)—R′, —(C═O)—NH—R′), —NH—R′, —NH—(C═O)—NH—R′, —NH—(C═O)—O—R′, O—(C═O)—NH—R′, —(C═O)—O—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, and
R y represents a group selected from the group consisting of:
—(CH 2 ) p —,
—NH—(CH 2 ) n NH—,
—S—(CH 2 ) q —S—,
—O—(CH 2 ) r —O—,
—[(XCH 2 CH 2 ) n ]—X—,
—[(C═O)—(CH 2 ) n —(C═O)]—,
—NH—[(C═O)—(CH 1 ) m —(C═O)]—NH—,
—[(C═O)—(CH 2 ) n —(C═O)]—O—,
—S—[(C═O)—(CH 2 ) n —(C═O)]—S—,
—O—[(C═O)—O—(CH 2 ) n —O—(C═O)]—O—,
—S—[(C═O)—S—(CH 2 ) n —S—(C═O)]—S—,
—[(C═O)—X—(CH 2 ) n —X—(C═O)]—,
wherein:
X, X 1 , and X 2 independently represent O, S, or NH,
p is an integer of 6 to 50,
q is an integer of 7 to 50,
r is an integer of 3 to 50,
m is an integer of 2 to 50, and
n is an integer of 1 to 50.
4. A sterically bulky stabilizer comprising a substituted pyridine derivative selected from the group consisting of the following compounds:
Groups X
R 1 = R 2 = R 3
R y
X 1 = X 2 = NH
H
X 1 = O X 2 = NH
H
X 1 = NH
H
X 1 = O
H
X 1 = O
H
X 1 = NH
H
wherein:
R 4 represents H, —NH—(C═O)—R′, —(C═O)—NH—R′, —NH—R′, —NH—(C═O)—NH—R′, —NH—(C═O)—O—R′, O—(C═O)—NH—R′, —(C═O)—O—R′, —O—(C═O)—R′, branched or linear alkyleneoxy chains, or —OR′, and
R′ is predominantly a linear or branched alkyl or cycloaliphatic group that may contain heteroatoms within the alkyl groups.
5. A sterically bulky stabilizer compound comprising a substituted pyridine derivative selected from the group consisting of the following compounds:
R 1
R 2
R 3
R 4
R 5
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
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