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 an alkylated derivative of an aromatic acid; and the presence of the associated stabilizer limits the extent of particle growth and aggregation, to afford nanoscale pigment particles.
1. A nanoscale pigment particle composition, comprising:
a benzimidazolone pigment, and
a sterically bulky stabilizer compound associated non-covalently with the benzimidazolone pigment, wherein the sterically bulky stabilizer compound comprises an aromatic acid derivative;
wherein presence of the sterically bulky stabilizer limits an extent of particle growth and aggregation, to afford nanoscale pigment particles.
2. The composition of claim 1 , wherein the nanoscale pigment particles have an average particle diameter as derived from transmission electron microscopy imaging, of less than about 150 nm.
3. The composition of claim 1 , wherein the benzimidazolone pigment comprises a diazo component group and a nucleophilic coupling component group that are linked together with at least one azo group, wherein at least one of the diazo component group and the nucleophilic coupling component group comprises a benzimidazolone moiety.
4. The composition of claim 3 , wherein the diazo component group is selected from the group consisting of DC 1 to DC 7 :
wherein:
* denotes a point of attachment to an amino group (—NH 2 ) in pigment precursor and a point of attachment to an azo group (—N═N—) in the benzimidazolone pigment,
R 1 to R 8 independently represent H; halogens; (CH 2 ) n CH 3 where n=0-6; OH;
alkoxyl groups —OR′ where R′ represents H, (CH 2) ) n CH 3 , or C 6 H 5 , and n represents a number of from 1 to about 6; CO 2 H; CO 2 CH 3 ; CO 2 (CH 2 ) n CH 3 wherein n=0-5; CONH 2 ; (CO)R′ wherein R′ can independently represent H, C 6 H 5 , (CH 2 ) n CH 3 wherein n=0-12, or (CH 2 ) n N(CH 3 ) 2 wherein n=1-6; OCH 3 ; OCH 2 CH 2 OH; NO 2 ; SO 3 H; or any of the following structural groups:
in DC 2 and DC 3 R′ represents H, (CH 2 ) n CH 3 , or C 6 H 5 , and n represents a number of from 1 to about 6, and
A represents —(CH 2 ) n — where n=0-6; —[O—(CH 2 ) n —O]— where n=0-6; [O—CH 2 CHR) n ]— where n=0-6 and R═H or CH 3 ; —(C═O)—; O; S; —(CH 2 ) n —(C═O)— where n=1-6; and —(C═O)—(CH 2 ) n (C═O)— where n=1-6.
5. The composition of claim 3 , wherein the nucleophilic coupling component group is selected from the group consisting of:
wherein R 9 , R 10 , R 11 , R 12 , and R 13 all independently represent H, Br, Cl, I, F, CH 3 , or OCH 3 , and * denotes a point of attachment to the azo group.
6. The composition of claim 1 , wherein the sterically bulky stabilizer is non-covalently associated with the benzimidazolone pigment predominantly by at least one of intra-molecular and inter-molecular hydrogen bonding, aromatic pi-stacking, and van der Waals forces.
7. The composition of claim 1 , wherein the sterically bulky stabilizer is a compound 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′, —NH—(C═O)—O—R′, O—(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 —COON 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.
8. The composition of claim 7 , wherein the sterically bulky group comprises a functional linker 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)—(CH 2 ), —(C═O)]—X—; —X—[(C═O)—X—(CH 2 ) n —X—(C═O)]—X—; and —[(C═O)—X—(CH 2 ) n —X—(C═O)]—, wherein X is defined as O, S, or NH and n is an integer of 1 to 50.
9. The composition of claim 7 , wherein the sterically bulky stabilizer is selected from the group consisting of:
where Y═OH or NH 2 , and X—R 1 and X—R 2 represent sterically bulky groups where R 1 and R 2 may be the same or different.
10. The composition of claim 7 , wherein the sterically bulky stabilizer is amphiphilic.
11. The composition of claim 7 , wherein the sterically bulky group comprises a functional group selected from the group consisting of —COOK, —NHCOR, —OR, and —CONHR, where R is a substituted or unsubstituted, linear, branched or cyclic alkyl group of 1 to 100 carbon atoms.
12. The composition of claim 7 , wherein the sterically bulky group comprises a moiety selected from the group consisting of
13. The composition of claim 1 , wherein the sterically bulky stabilizer is a compound 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)—(CH 2 ) n —(C═O)]—X—; —X—[(C═O)—X—(CH 2 ) n —X—(C═O)]—X—; and —[(C═O)—X—(CH 2 ) n —X—(C═O)]—, wherein X is defined as O, S, or NH and n is an integer of 1 to 50.
14. The composition of claim 13 , wherein R y is 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)—(CH 2 ) n —(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.
15. The composition of claim 1 , wherein the sterically bulky stabilizer compound comprises 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
—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
—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
—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
—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
—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
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
H
H
H
R y
R 1
R 2
X = NH
H
—COOH
X = O
H
—COOH
X = NH
H
—COOH
X = O
H
—COOH
X 1 = X 2 = NH
H
—COOH
X 1 = O, X 2 = NH
H
—COOH
X = NH
H
—CONH 2
X = O
H
—CONH 2
X = NH
H
—CONH 2
X = O
H
—CONH 2
X 1 = X 2 = NH
H
—CONH 2
X 1 = O, X 2 = NH
H
—CONH 2
X = NH
H
—COOH
X = O
H
—COOH
X = NH
H
—COOH
X = O
H
—COOH
X 1 = X 2 = NH
H
—COOH
X 1 = O, X 2 = NH
H
—COOH
X = NH
H
H
X = O
H
H
X = NH
H
H
X = O
H
H
X 1 = X 2 = NH
H
H
X 1 = O, X 2 = NH
H
H
X = NH
H
H
X = O
H
H
X = NH
H
H
X = O
H
H
X 1 = X 2 = NH
H
H
X 1 = O, X 2 = NH
H
H
X = NH
—COOH
H
X = O
—COOH
H
X = NH
—COOH
H
X = O
—COOH
H
X 1 = X 2 = NH
—COOH
H
X 1 = O, X 2 = NH
—COOH
H
X = NH
—CONH 2
H
X = O
—CONH 2
H
X = NH
—CONH 2
H
X = O
—CONH 2
H
X 1 = X 2 = NH
—CONH 2
H
X 1 = O, X 2 = NH
—CONH 2
H
R 2
R 3
R 4
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
—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
—COOH
H
H
—COOH
—COOH
H
H
—COOH
—COOH
H
H
—COOH
—COOH
H
H
—COOH
—COOH
H
H
—COOH
—COOH
H
H
H
—COOH
H
H
H
—COOH
H
H
H
—COOH
H
H
H
—COOH
H
H
H
—COOH
H
H
H
—COOH
H
H
H
—CONH 2
H
H
H
—CONH 2
H
H
H
—CONH 2
H
H
H
—CONH 2
H
H
H
—CONH 2
H
H
H
—CONH 2
H
H
H
H
—COOH
H
H
H
—COOH
H
H
H
—COOH
H
H
H
—COOH
H
H
H
—COOH
H
H
H
—COOH
H
H
H
—CONH 2
H
H
H
—CONH 2
H
H
H
—CONH 2
H
H
H
—CONH 2
H
H
H
—CONH 2
H
H
H
—CONH 2
H.
16. The composition of claim 1 , further comprising a surfactant selected from the group consisting of derivatives of rosin natural products; long-chain or branched hydrocarbon alcohols; alcohol ethoxylates; acrylic-based polymers; styrene-based copolymers; copolymers of α-olefins; copolymers of vinyl pyridine, vinyl imidazole, and vinyl pyrrolidinone; polyester copolymers; polyamide copolymers; and copolymers of acetals and acetates.
17. The composition of claim 1 , wherein the nanoscale pigment particles have an aspect ratio of 1:1 to about 7:1.
18. The composition of claim 1 , wherein the nanoscale pigment particles have a shape selected from the group consisting of rods, platelets, needles, prisms, and substantially spherical.
19. A marking material composition comprising the nanoscale pigment particle composition of claim 1 , wherein the marking material composition is an ink composition or a toner composition.
20. An electrophotographic photoreceptor comprising the nanoscale pigment particle composition of claim 1 .
21. A solar cell comprising an organic photo conducting material comprising the nanoscale pigment particle composition of claim 1 .
22. A biological or chemical sensor comprising the nanoscale pigment particle composition of claim 1 .