Non-aqueous compositions containing nanosized particles of monoazo laked pigment
View Patent ↗Non-aqueous disperson compositions, such as ink compositions, contain a polymeric dispersant, a polymeric resin, an organic liquid, and a nanoscale pigment particle composition including an organic monoazo laked pigment including at least one functional moiety, and a sterically bulky stabilizer compound including at least one functional group, wherein the functional moiety of the pigment associates non-covalently with the functional group of the stabilizer; and the presence of the associated stabilizer limits the extent of particle growth and aggregation, to afford nanoscale-sized pigment particles.
1. A non-aqueous dispersion composition comprising:
a non-aqueous carrier,
a polymeric dispersant,
a polymer resin, and
a nanoscale pigment particle composition comprising:
an organic monoazo laked pigment having at least one functional moiety, and
a sterically bulky stabilizer compound having at least one functional group,
wherein the functional moiety of the pigment associates non-covalently with the functional group of the stabilizer; and
presence of the associated stabilizer limits an extent of particle growth and aggregation, so as to afford nanoscale-sized pigment particles.
2. The composition of claim 1 , wherein the nanoscale pigment particle composition imparts color to the non-aqueous dispersion composition.
3. The composition of claim 1 , wherein the carrier is present in an amount of about 50 to about 99.9 weight %, and said nanoscale pigment particle composition is present in an amount of about 0.1 to about 50 weight % by weight of the non-aqueous dispersion composition.
4. The composition of claim 1 , wherein the polymeric dispersant is selected from the group consisting of derivatives of rosin natural products, acrylic-based polymers, styrene-based copolymers, copolymers of α-olefins, copolymers of vinyl pyridine, vinyl imidazole, vinyl pyrrolidinone, polyester copolymers, polyamide copolymers, copolymers of acetals, poly(vinyl butyral-co-vinyl alcohol-co-vinyl acetate), poly(vinyl acetate), poly(acrylic acid), poly(methacrylic acid), poly(vinyl alcohol), poly(N-vinylcarbazole), poly(methyl methacrylate), polyvinylidene difluoride, polyesters, polycarbonate polymers, poly(2-hydroxyethyl methacrylate), poly(styrene-b-4-vinylpyridine), polyurethane resins, polyetheretherketones, phenol-formaldehyde resins, polyols, glycolic polymers, polysulfones, polyarylethers, and polyarylsulfones.
5. The composition of claim 1 , wherein the polymeric dispersant is selected from the group consisting of copolymers of 1-hexadecene, copolymers of 1-octadecene, copolymers of 1-eicosene, copolymers of 1-triacontene, poly(vinyl butyral-co-vinyl alcohol-co-vinyl acetate), poly(vinyl acetate), poly(acrylic acid), poly(methacrylic acid), poly(vinyl alcohol), poly(methyl methacrylate), polyester, polycarbonate, poly(styrene-b-4-vinylpyridine), polyethylene glycol polymers and their derivatives, and mixtures thereof.
6. The composition of claim 1 , wherein the carrier is selected from the group consisting of acetone, acetonitrile, methyl acetate, ethyl acetate, n-butyl acetate, methoxypropylacetate, tetrahydrofuran, methanol, ethanol, n-propanol, iso-propanol, n-butanol, iso-butanol, sec-butanol, propylene glycol monomethyl ether, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, dipropylene glycol methyl ether, propylene glycol methyl ether acetate, methyl ethyl ketone, methyl isobutyl, ketone, toluene, o-xylene, m-xylene, p-xylene, monochlorobenzene, chloromethane, dichloromethane, drying oils, non-drying oils, and mixtures thereof.
7. The composition of claim 1 , wherein the composition is an ink composition.
8. The composition of claim 1 , further comprising at least one additive selected from the group consisting of surfactants, light stabilizers, UV absorbers, optical brighteners, thixotropic agents, dewetting agents, slip agents, foaming agents, antifoaming agents, flow agents, oils, plasticizers, binders, electrical conductive agents, fungicides, bactericides, organic and inorganic filler particles, leveling agents, opacifiers, antistatic agents, dispersants, drying agents, and mixtures thereof.
9. The composition of claim 1 , further comprising an additional colorant different from said nanoscale pigment particle composition, selected from the group consisting of pigment, dye, mixtures of pigment and dye, mixtures of pigments, mixtures of dyes, and the like.
10. The composition of claim 1 , wherein the nanoscale-sized pigment particles have an average particle diameter, as derived from transmission electron microscopy imaging, of less than about 200 nm.
11. The composition of claim 1 , wherein the at least one functional moiety of the organic monoazo laked pigment is selected from the group consisting of sulfonate/sulfonic acid, (thio)carboxylate/(thio)carboxylic acid, phosphonate/phosphonic acid, ammonium and substituted ammonium salts, phosphonium and substituted phosphonium salts, substituted carbonium salts, substituted arylium salts, alkyl/aryl (thio)carboxylate esters, thiol esters, primary and secondary amides, primary and secondary amines, hydroxyl, ketone, aldehyde, oxime, hydroxylamino, enamines, porphyrins, (phthalo)cyanines, urethane, carbamate, substituted ureas, guanidines and guanidinium salts, pyridine and pyridinium salts, imidazolium and (benz)imidazolium salts, (benz)imidazolones, pyrrolo, pyrimidine and pyrimidinium salts, pyridinone, piperidine and piperidinium salts, piperazine and piperazinium salts, triazolo, tetraazolo, oxazole, oxazolines and oxazolinium salts, indoles, indenones, and mixtures thereof.
12. The composition of claim 1 , wherein the organic monoazo laked pigment comprises a diazonium component linked to a coupling component through an azo or hydrazone group, with a counterion.
13. The composition of claim 12 , wherein a precursor to the diazonium component of the monoazo laked pigment is a compound of Formula (2):
where R 1 , R 2 , and R 3 independently represent H, a straight or branched alkyl group of from about 1 to about 10 carbon atoms, halogen, NH 2 , NO 2 , CO 2 H, or CH 2 CH 3 ; and FM represents SO 3 H, —C(═O)—NH-Aryl-SO 3 − (where Aryl represents an aryl group that can be unsubstituted or substituted with either halogens or alkyl groups having from about 1 to about 10 carbons), CO 2 H, halogen, NH 2 , or —C(═O)—NH 2 , or is a compound of Formula (3):
14. The composition of claim 13 , wherein the precursor to the diazonium component is selected from the group consisting of the following compounds of Formula (2) wherein:
FM is SO 3 H, R 1 is CH 3 , R 2 is H, and R 3 is NH 2 ,
FM is SO 3 H, R 1 is CH 3 , R 2 is Cl, and R 3 is NH 2 ,
FM is SO 3 H, R 1 is Cl, R 2 is CH 3 , and R 3 is NH 2 ,
FM is SO 3 H, R 1 is Cl, R 2 is CO 2 H, and R 3 is NH 2 ,
FM is SO 3 H, R 1 is Cl, R 2 is CH 2 CH 3 , and R 3 is NH 2 ,
FM is SO 3 H, R 1 is Cl, R 2 is Cl, and R 3 is NH 2 ,
FM is SO 3 H, R 1 is H, R 2 is NH 2 , and R 3 is H,
FM is SO 3 H, R 1 is H, R 2 is NH 2 , and R 3 is CH 3 ,
FM is SO 3 H, R 1 is NH 2 , R 2 is H, and R 3 is Cl,
FM is SO 3 H, R 1 is H, R 2 is H, and R 3 is NH 2 ,
FM is SO 3 H, R 1 is H, R 2 is NH 2 , and R 3 is H,
FM is SO 3 H, R 1 is NO 2 , R 2 is NH 2 , and R 3 is H,
FM is —C(═O) —NH-Phenyl-SO 3 - , R 1 is NH 2 , R 2 is CH 3 , and R 3 is H,
FM is CO 2 H, R 1 is H, R 2 is H, and R 3 is NH 2 ,
FM is Cl, R 1 is H, R 2 is H, and R 3 is NH 2 ,
FM is NH 2 , R 1 is CH 3 , R 2 is H, and R 3 is H,
FM is NH 2 , R 1 is H, R 2 is CH 3 , and R 3 is H,
FM is —C(═O)NH 2 , R 1 is NH 2 , R 2 is CH 3 , and R 3 is H,
FM is —C(═O)NH 2 , R 1 is H, R 2 is NH 2 , and R 3 is H, and
FM is NH 2 , R 1 is H, R 2 is H, and R 3 is H.
15. The composition of claim 12 , wherein a precursor to the coupling component of the monoazo laked pigment is selected from the group consisting of β-naphthol and derivatives thereof, naphthalene sulfonic acid derivatives, pyrazolone derivatives, and acetoacetic arylide derivatives.
16. The composition of claim 12 , wherein a precursor to the coupling component is selected from the group consisting of compounds of Formulas (4)-(8), wherein * denotes a point of coupling or attachment to the azo or hydrazone group:
where FM represents H, CO 2 H, SO 3 H, —C(═O)-NH-Aryl-SO 3 − where the aryl group can be unsubstituted or substituted with either halogens, or alkyl groups having from about 1 to about 10 carbons, CO 2 H, halogen, NH 2 , —C(═O)—NH 2 , substituted benzamides, or benzimidazolone amides;
where FM represents SO 3 H, CO 2 H, —C(═O)-NH-Aryl-SO 3 − where the aryl group can be unsubstituted or substituted with either halogens, or alkyl groups having from about 1 to about 10 carbons, CO 2 H, halogens, NH 2 , —C(═O)—NH 2 groups R 3 and R 4 independently represent H, SO 3 H;
where FM represents SO 3 H, CO 2 H, —C(═O) —NH-Aryl-SO 3 − where the aryl group can be unsubstituted or substituted with either halogens, or alkyl groups having from about 1 to about 10 carbons, CO 2 H, halogens, NH 2 , —C(═O) —NH 2 ; R 1 , R 2 , R 3 and R 4 independently represent H, SO 3 H, —C(═O)—NH-Phenyl;
where G represents CO 2 H, straight or branched alkyl having from 1 to about 10 carbons atoms; and R 1 ′, R 2 ′, R 3 ′ and R 4 ′ independently represent H, halogens, SO 3 H, NO 2 or alkoxyl groups;
where R 1 ′ represents a straight or branched alkyl group having from 1 to about 10 carbon atoms, R 2 ′ represents
where each of R a , R b , and R c independently represents H, a straight or branched alkyl group having from 1 to about 10 carbon atoms, OCH 3 , or halogens.
17. The composition of claim 12 , wherein the counterion is selected from the group consisting of metals, non-metals, and cations or anions based on either carbon, nitrogen or phosphorus.
18. The composition of claim 1 , wherein the at least one functional group of the sterically bulky stabilizer is selected from the group consisting of sulfonate/sulfonic acid, (thio)carboxylate/(thio)carboxylic acid, phosphonate/phosphonic acid, ammonium and substituted ammonium salts, phosphonium and substituted phosphonium salts, substituted carbonium salts, substituted arylium salts, alkyl/aryl (thio)carboxylate esters, thiol esters, primary and secondary amides, primary and secondary amines, hydroxyl, ketone, aldehyde, oxime, hydroxylamino, enamines, porphyrins, (phthalo)cyanines, urethane, carbamate, substituted ureas, guanidines and guanidinium salts, pyridine and pyridinium salts, imidazolium and (benz)imidazolium salts, (benz)imidazolones, pyrrolo, pyrimidine and pyrimidinium salts, pyridinone, piperidine and piperidinium salts, piperazine and piperazinium salts, triazolo, tetraazolo, oxazole, oxazolines and oxazolinium salts, indoles, indenones, and mixtures thereof.
19. The composition of claim 1 , wherein the sterically bulky stabilizer comprises at least one aliphatic hydrocarbon moiety.
20. The composition of claim 1 , further comprising adding a surfactant selected from the group consisting of rosin-type compounds; acrylic-based polymers; styrene-based copolymers; copolymers of a-olefins; copolymers of vinyl pyridine, vinyl imidazole, and vinyl pyrrolidinone; polyester copolymers; polyamide copolymers; and copolymers of vinyl acetals and vinyl acetates, and mixtures thereof
21. The composition of claim 1 , wherein the non-covalent association between the organic monoazo laked pigment and the sterically bulky stabilizer compound is at least one of van der Waals' forces, ionic bonding, coordination bonding, hydrogen bonding, and aromatic pi-stacking bonding.
22. The composition of claim 1 , wherein the nano-sized monoazo laked pigment composition has tunable coloristic properties as a function of particle size of the nano-sized particles.
23. The composition of claim 1 , wherein the sterically bulky stabilizer is selected from the group consisting of the following compounds: