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Nanosized particles of monoazo laked pigment with tunable properties

a monoazo laked pigment and nanoscale technology, applied in the field of nanoscale pigment particle compositions, can solve the problems of poor ink performance, poor lightfastness, poor image quality and showthrough,

Active Publication Date: 2008-12-11
XEROX CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The present patent provides a solution for creating nanoscale pigment particles with adjustable coloristic properties. These particles are composed of an organic monoazo laked pigment and a sterically bulky stabilizer compound. The functional moiety of the pigment associates non-covalently with the functional group of the stabilizer, resulting in a stable and uniform particle size. The nanoscale pigment particles can be used to create thin film coatings with vivid and adjustable color properties. The patent also provides a process for preparing these nanoscale pigment particles.

Problems solved by technology

However, since dyes are molecularly dissolved in the ink vehicle, they are often susceptible to unwanted interactions that lead to poor ink performance, for example photooxidation from light (will lead to poor lightfastness), dye diffusion from the ink into paper or other substrates (will lead to poor image quality and showthrough), and the ability for the dye to leach into another solvent that makes contact with the image (will lead to poor water / solventfastness).
Key challenges with using pigments for inkjet inks are their large particle sizes and wide particle size distribution, the combination of which can pose critical problems with reliable jetting of the ink (i.e. inkjet nozzles are easily blocked).
Kazuyuki Hayashi et al., “Uniformed nano-downsizing of organic pigments through core-shell structuring,” Journal of Materials Chemistry, 17(6), 527-530 (2007) discloses that mechanical dry milling of organic pigments in the presence of mono-dispersed silica nanoparticles gave core-shell hybrid pigments with uniform size and shape reflecting those of the inorganic particles, in striking contrast to conventional milling as a breakdown process, which results in limited size reduction and wide size distribution.

Method used

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  • Nanosized particles of monoazo laked pigment with tunable properties
  • Nanosized particles of monoazo laked pigment with tunable properties
  • Nanosized particles of monoazo laked pigment with tunable properties

Examples

Experimental program
Comparison scheme
Effect test

example 1

Synthesis of Nano-Sized Particles of Pigment Red 57:1 by a Two-Step Method

[0096]Step 1: Diazotization and Coupling: Into a 500 mL round bottom flask equipped with a mechanical stirrer, thermometer, and addition funnel was dissolved 2-amino-5-methylbenzenesulfonic acid (8.82 g) into 0.5M KOH aqueous solution (97.0 mL). The resulting brown solution was cooled to 0° C. A 20 wt % aqueous solution of sodium nitrite (NaNO2; 3.28 g dissolved into 25 mL water) was added slowly to the first solution while maintaining the temperature below 3° C. To the red-brown homogeneous mixture was added dropwise concentrated HCl (10M, 14.15 mL) over 1 hour, maintaining the internal temperature below 2° C. The mixture formed a pale brown suspension, and following complete addition of conc. HCl, the suspension was stirred an additional 30 min.

[0097]In a separate 2-L resin kettle was dissolved 3-hydroxy-2-naphthoic acid (8.86 g) into an aqueous solution of KOH (8.72 g) in water (100 mL). An additional 250 m...

example 2

Synthesis of Nano-Sized Particles of Pigment Red 57:1 by a Two-Step Method

[0100]The procedure of Step 1 of Example 1 above was reproduced.

[0101]Step 2: Laking

[0102]Into a 500 mL round bottom flask equipped with mechanical stirrer and condenser was charged 126 g of aqueous slurry of Lithol Rubine-Potassium salt dye from above (Example 1) having about 1.6% wt solids content. The pH of the slurry was adjusted to at least 9.0 or higher by addition of 0.5 M KOH solution, after which the dyestuff was fully dissolved. An aqueous solution 5 wt % Dresinate X (4.0 mL) was added, followed by a solution containing sodium dioctyl sulfosuccinate (0.96 g) dissolved in 100 mL of 90:10 deionized water / THF mixture. No visible change was observed. An aqueous solution of calcium chloride dihydrate (0.5 M solution, 13 mL) was added dropwise to the slurry while stirring vigorously. A red precipitate formed immediately, and after complete addition of the calcium chloride solution, the slurry was stirred f...

example 3

Synthesis of Nano-Sized Particles of Pigment Red 57:1 by a Two-Step Method

[0103]Step 1: Diazotization and Coupling: Into a 500 mL round bottom flask equipped with a mechanical stirrer, thermometer, and addition funnel was dissolved 2-amino-5-methylbenzenesulfonic acid (12.15 g) into 0.5M KOH aqueous solution (135 mL). The resulting brown solution was cooled to 0° C. A 20 wt % aqueous solution of sodium nitrite (NaNO2; 4.52 g dissolved into 30 mL water) was added slowly to the first solution while maintaining the temperature below −2° C. Concentrated HCl (10M, 19.5 mL) was then slowly added dropwise over 1 hour while maintaining the internal temperature below 0° C. The mixture formed a pale brown suspension and following complete addition of conc. HCl, the suspension was stirred an additional 30 min.

[0104]In a separate 2-L resin kettle was dissolved 3-hydroxy-2-naphthoic acid (12.2 g) into an aqueous solution of KOH (12.0 g) in water (130 mL). An additional 370 mL of water was added,...

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Abstract

A nanoscale pigment particle composition includes 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 on the pigment associates non-covalently with the functional group of the stabilizer; and the nanoscale pigment particles have an average particle size of from about 10 nm to about 500 nm and have tunable coloristic properties that depend on both particle composition and average particle size.

Description

[0001]This application is a continuation-in-part of U.S. patent application Ser. No. 11 / 759,913 to Rina Carlini et al. filed Jun. 7, 2007, the entire disclosure of which is incorporated herein by reference.TECHNICAL FIELD[0002]This disclosure is generally directed to nanoscale pigment particle compositions, and methods for producing such nanoscale pigment particle compositions, as well as to uses of such compositions, for example, in ink compositions. More specifically, this disclosure is directed to organic mono-azo laked nanoscale pigments with tunable properties such as particle size, coloristic properties, and properties as pigmented liquid dispersions. Such particles are useful, for example, as nanoscopic colorants for such compositions as inks, toners and the like.CROSS-REFERENCE TO RELATED APPLICATIONS[0003]Disclosed in commonly assigned U.S. patent application Ser. No. 11 / 759,913 to Rina Carlini et al. filed Jun. 7, 2007, is a nanoscale pigment particle composition, comprisi...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C09B63/00
CPCB82Y30/00C09B63/005C09B67/0005C09B67/0009C09B67/0013C09D7/007C09D11/037C09D11/101C09D11/322C09D11/34C09D11/36C09D7/41
Inventor ALLEN, C. GEOFFREYCARLINI, RINAGARDNER, SANDRA J.
Owner XEROX CORP
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