Developer compositions

A toner composition for the development of electrostatic latent images comprising particles comprising a mixture of a resin and a colorant selected from the group consisting of:

• (a) the following formulae, wherein R.sub.1 and R'.sub.1 are each electron withdrawing groups, R.sub.2 and R'.sub.2 are each independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, and substituted arylalkyl, R.sub.3 and R'.sub.3 are each independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, and substituted arylalkyl, Ar and Ar' are each independently selected from the group consisting of aryl, substituted aryl, arylalkyl, and substituted arylalkyl, and X is selected from the group consisting of alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, and substituted arylalkyl, wherein the substituents on the substituted alkyl, substituted aryl, and substituted arylalkyl groups are selected from the group consisting of silyl groups, halide atoms, nitro groups, amine groups, hydroxy groups, alkoxy groups, ether groups, aldehyde groups, ketone groups, ester groups, amide groups, and carboxylic acid groups:
• ##STR96## wherein R is a group that meets the definitions of both R.sub.1 and R'.sub.2 ##STR97## wherein R is a group that meets the definitions of both R.sub.1 and R'.sub.3 ##STR98## wherein R is a group that meets the definitions of both R.sub.1 and Ar' ##STR99## wherein R is a group that meets the definitions of both R.sub.2 and R'.sub.3 ##STR100## wherein R is a group that meets the definitions of both R.sub.2 and Ar' ##STR101## wherein R is a group that meets the definitions of both R.sub.3 and Ar' ##STR102## (b) those of the following formulae, wherein R.sub.1 and R'.sub.1 are each independently selected from the group consisting of hydrogen, alkyl, and substituted alkyl, R.sub.2 and R'.sub.2 are each independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, and substituted arylalkyl, Ar and Ar' are each independently selected from the group consisting of aryl, substituted aryl, arylalkyl, and substituted arylalkyl, and Y is selected from the group consisting of alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, and substituted arylalkyl, wherein the substituents on the substituted alkyl, substituted aryl, and substituted arylalkyl groups are selected from the group consisting of silyl groups, halide atoms, nitro groups, amine groups, hydroxy groups, alkoxy groups, ether groups, aldehyde groups, ketone groups, ester groups, and carboxylic acid groups:
• ##STR103## wherein R is a group that meets the definitions of both Ar and R'.sub.1 ##STR104## wherein R is a group that meets the definitions of both Ar and R'.sub.2 ##STR105## wherein R is a group that meets the definitions of both R.sub.1 and R'.sub.2 ##STR106## (c) those of the following formulae, wherein R.sub.1 and R'.sub.1 are each independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, and substituted arylalkyl, R.sub.2 and R'.sub.2 are each independently selected from the group consisting of aryl, substituted aryl, arylalkyl, and substituted arylalkyl, Ar and Ar' are each independently selected from the group consisting of aryl, substituted aryl, arylalkyl, and substituted arylalkyl, and Y is selected from the group consisting of alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, and substituted arylalkyl, wherein the substituents on the substituted alkyl, substituted aryl, and substituted arylalkyl groups are selected from the group consisting of silyl groups, halide atoms, nitro groups, amine groups, hydroxy groups, alkoxy groups, ether groups, aldehyde groups, ketone groups, ester groups, and carboxylic acid groups:
• ##STR107## wherein R is a group that meets the definitions of both Ar and R'.sub.1 ##STR108## wherein R is a group that meets the definitions of both Ar and R'.sub.2 ##STR109## wherein R is a group that meets the definitions of both R.sub.1 and R'.sub.2 ##STR110## (d) those of the following formulae, wherein R.sub.1 is an electron withdrawing group, R.sub.2 is selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, and substituted arylalkyl, R3 is selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, and substituted arylalkyl, Ar is selected from the group consisting of aryl, substituted aryl, arylalkyl, and substituted arylalkyl, R'.sub.1 is selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, and substituted arylalkyl, R'.sub.2 is selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, and substituted arylalkyl, Ar' is selected from the group consisting of aryl, substituted aryl, arylalkyl, and substituted arylalkyl, and Z is selected from the group consisting of alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, and substituted arylalkyl, wherein the substituents on the substituted alkyl, substituted aryl, and substituted arylalkyl groups are selected from the group consisting of silyl groups, halide atoms, nitro groups, amine groups, hydroxy groups, alkoxy groups, ether groups, aldehyde groups, ketone groups, ester groups, amide groups, and carboxylic acid groups:
• ##STR111## wherein R is a group that meets the definitions of both R.sub.1 and Ar' ##STR112## wherein R is a group that meets the definitions of both R.sub.1 and R'.sub.1 ##STR113## wherein R is a group that meets the definitions of both R.sub.1 and R'.sub.2 ##STR114## wherein R is a group that meets the definitions of both R.sub.2 and Ar' ##STR115## wherein R is a group that meets the definitions of both R.sub.2 and R'.sub.1 ##STR116## wherein R is a group that meets the definitions of both R.sub.2 and R'.sub.2 ##STR117## wherein R is a group that meets the definitions of both R.sub.3 and Ar' ##STR118## wherein R is a group that meets the definitions of both R.sub.3 and R'.sub.1 ##STR119## wherein R is a group that meets the definitions of both R.sub.3 and R'.sub.2 ##STR120## wherein R is a group that meets the definitions of both Ar and Ar' ##STR121## wherein R is a group that meets the definitions of both Ar and R'.sub.1 ##STR122## wherein R is a group that meets the definitions of both Ar and R'.sub.2 ##STR123## and (e) mixtures thereof.

A liquid developer composition for the development of electrostatic latent images which comprises a nonaqueous liquid vehicle and a colorant selected from the group consisting of:

• (a) dimeric compounds containing one moiety of Formula I ##STR124## wherein R.sub.1 is an electron withdrawing group, R.sub.2 is selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, and substituted arylalkyl, R.sub.3 is selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, and substituted arylalkyl, and Ar is selected from the group consisting of aryl, substituted aryl, arylalkyl, and substituted arylalkyl, wherein the substituents on the substituted alkyl, substituted aryl, and substituted arylalkyl groups are selected from the group consisting of silyl groups, halide atoms, nitro groups, amine groups, hydroxy groups, alkoxy groups, ether groups, aldehyde groups, ketone groups, ester groups, amide groups, and carboxylic acid groups;
• and one moiety of Formula II ##STR125## wherein R.sub.1 is selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, and substituted arylalkyl, R.sub.2 is selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, and substituted arylalkyl, and Ar is selected from the group consisting of aryl, substituted aryl, arylalkyl, and substituted arylalkyl, wherein the substituents on the substituted alkyl, substituted aryl, and substituted arylalkyl groups are selected from the group consisting of silyl groups, halide atoms, nitro groups, amine groups, hydroxy groups, alkoxy groups, ether groups, aldehyde groups, ketone groups, ester groups, and carboxylic acid groups;
• (b) trimeric compounds containing three moieties of Formula I;
• (c) trimeric compounds containing two moieties of Formula I and one moiety of Formula II;
• (d) trimeric compounds containing one moiety of Formula I and two moieties of Formula II;
• and (e) mixtures thereof, wherein the liquid developer has a resistivity of from about 10.sup.8 to about 10.sup.11 ohm-cm and a viscosity of from about 25 to about 500 centipoise.

A liquid developer composition for the development of electrostatic latent images which comprises a nonaqueous liquid vehicle and a colorant selected from the group consisting of:

• (a) the following formulae, wherein R.sub.1 and R'.sub.1 are each electron withdrawing groups, R.sub.2 and R'.sub.2 are each independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, and substituted arylalkyl, R.sub.3 and R'.sub.3 are each independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, and substituted arylalkyl, Ar and Ar' are each independently selected from the group consisting of aryl, substituted aryl, arylalkyl, and substituted arylalkyl, and X is selected from the group consisting of alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, and substituted arylalkyl, wherein the substituents on the substituted alkyl, substituted aryl, and substituted arylalkyl groups are selected from the group consisting of silyl groups, halide atoms, nitro groups, amine groups, hydroxy groups, alkoxy groups, ether groups, aldehyde groups, ketone groups, ester groups, amide groups, and carboxylic acid groups:
• ##STR126## wherein R is a group that meets the definitions of both R.sub.1 and R'.sub.2 ##STR127## wherein R is a group that meets the definitions of both R.sub.1 and R'.sub.3 ##STR128## wherein R is a group that meets the definitions of both R.sub.1 and Ar' ##STR129## wherein R is a group that meets the definitions of both R.sub.2 and R'.sub.3 ##STR130## wherein R is a group that meets the definitions of both R.sub.2 and Ar' ##STR131## wherein R is a group that meets the definitions of both R.sub.3 and Ar' ##STR132## (b) those of the following formulae, wherein R.sub.1 and R'.sub.1 are each independently selected from the group consisting of hydrogen, alkyl, and substituted alkyl, R.sub.2 and R'.sub.2 are each independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, and substituted arylalkyl, Ar and Ar' are each independently selected from the group consisting of aryl, substituted aryl, arylalkyl, and substituted arylalkyl, and Y is selected from the group consisting of alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, and substituted arylalkyl, wherein the substituents on the substituted alkyl, substituted aryl, and substituted arylalkyl groups are selected from the group consisting of silyl groups, halide atoms, nitro groups, amine groups, hydroxy groups, alkoxy groups, ether groups, aldehyde groups, ketone groups, ester groups, and carboxylic acid groups:
• ##STR133## wherein R is a group that meets the definitions of both Ar and R'.sub.1 ##STR134## wherein R is a group that meets the definitions of both Ar and R'.sub.2 ##STR135## wherein R is a group that meets the definitions of both R.sub.1 and R'.sub.2 ##STR136## (c) those of the following formulae, wherein R.sub.1 and R'.sub.1 are each independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, and substituted arylalkyl, R.sub.2 and R'.sub.2 are each independently selected from the group consisting of aryl, substituted aryl, arylalkyl, and substituted arylalkyl, Ar and Ar' are each independently selected from the group consisting of aryl, substituted aryl, arylalkyl, and substituted arylalkyl, and Y is selected from the group consisting of alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, and substituted arylalkyl, wherein the substituents on the substituted alkyl, substituted aryl, and substituted arylalkyl groups are selected from the group consisting of silyl groups, halide atoms, nitro groups, amine groups, hydroxy groups, alkoxy groups, ether groups, aldehyde groups, ketone groups, ester groups, and carboxylic acid groups:
• ##STR137## wherein R is a group that meets the definitions of both Ar and R'.sub.1 ##STR138## wherein R is a group that meets the definitions of both Ar and R'.sub.2 ##STR139## wherein R is a group that meets the definitions of both R.sub.1 and R'.sub.2 ##STR140## (d) those of the following formulae, wherein R.sub.1 is an electron withdrawing group, R.sub.2 is selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, and substituted arylalkyl, R.sub.3 is selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, and substituted arylalkyl, Ar is selected from the group consisting of aryl, substituted aryl, arylalkyl, and substituted arylalkyl, R'.sub.1 is selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, and substituted arylalkyl, R'.sub.2 is selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, and substituted arylalkyl, Ar' is selected from the group consisting of aryl, substituted aryl, arylalkyl, and substituted arylalkyl, and Z is selected from the group consisting of alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, and substituted arylalkyl, wherein the substituents on the substituted alkyl, substituted aryl, and substituted arylalkyl groups are selected from the group consisting of silyl groups, halide atoms, nitro groups, amine groups, hydroxy groups, alkoxy groups, ether groups, aldehyde groups, ketone groups, ester groups, amide groups, and carboxylic acid groups:
• ##STR141## wherein R is a group that meets the definitions of both R.sub.1 and Ar' ##STR142## wherein R is a group that meets the definitions of both R.sub.1 and R'.sub.1 ##STR143## wherein R is a group that meets the definitions of both R.sub.1 and R'.sub.2 ##STR144## wherein R is a group that meets the definitions of both R.sub.2 and Ar' ##STR145## wherein R is a group that meets the definitions of both R.sub.2 and R'.sub.1 ##STR146## wherein R is a group that meets the definitions of both R.sub.2 and R'.sub.2 ##STR147## wherein R is a group that meets the definitions of both R.sub.3 and Ar' ##STR148## wherein R is a group that meets the definitions of both R.sub.3 and R'.sub.1 ##STR149## wherein R is a group that meets the definitions of both R.sub.3 and R'.sub.2 ##STR150## wherein R is a group that meets the definitions of both Ar and Ar' ##STR151## wherein R is a group that meets the definitions of both Ar and R'.sub.1 ##STR152## wherein R is a group that meets the definitions of both Ar and R'.sub.2 ##STR153## and (e) mixtures thereof, wherein the liquid developer has a resistivity of from about 10.sup.8 to about 10.sup.11 ohm-cm and a viscosity of from about 25 to about 500 centipoise.

A liquid developer composition for the development of electrostatic latent images which comprises a nonaqueous liquid vehicle, a charge control agent, and toner particles comprising a mixture of a resin and a colorant selected from the group consisting of:

• (a) dimeric compounds containing one moiety of Formula I ##STR154## wherein R.sub.1 is an electron withdrawing group, R.sub.2 is selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, and substituted arylalkyl, R.sub.3 is selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, and substituted arylalkyl, and Ar is selected from the group consisting of aryl, substituted aryl, arylalkyl, and substituted arylalkyl, wherein the substituents on the substituted alkyl, substituted aryl, and substituted arylalkyl groups are selected from the group consisting of silyl groups, halide atoms, nitro groups, amine groups, hydroxy groups, alkoxy groups, ether groups, aldehyde groups, ketone groups, ester groups, amide groups, and carboxylic acid groups;
• and one moiety of Formula II ##STR155## wherein R.sub.1 is selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, and substituted arylalkyl, R.sub.2 is selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, and substituted arylalkyl, and Ar is selected from the group consisting of aryl, substituted aryl, arylalkyl, and substituted arylalkyl, wherein the substituents on the substituted alkyl, substituted aryl, and substituted arylalkyl groups are selected from the group consisting of silyl groups, halide atoms, nitro groups, amine groups, hydroxy groups, alkoxy groups, ether groups, aldehyde groups, ketone groups, ester groups, and carboxylic acid groups;
• (b) trimeric compounds containing three moieties of Formula I;
• (c) trimeric compounds containing two moieties of Formula I and one moiety of Formula II;
• (d) trimeric compounds containing one moiety of Formula I and two moieties of Formula II;
• and (e) mixtures thereof.

A liquid developer composition for the development of electrostatic latent images which comprises a nonaqueous liquid vehicle, a charge control agent, and toner particles comprising a mixture of a resin and a colorant selected from the group consisting of:

• (a) the following formulae, wherein R.sub.1 and R'.sub.1 are each electron withdrawing groups, R.sub.2 and R'.sub.2 are each independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, and substituted arylalkyl, R.sub.3 and R'.sub.3 are each independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, and substituted arylalkyl, Ar and Ar' are each independently selected from the group consisting of aryl, substituted aryl, arylalkyl, and substituted arylalkyl, and X is selected from the group consisting of alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, and substituted arylalkyl, wherein the substituents on the substituted alkyl, substituted aryl, and substituted arylalkyl groups are selected from the group consisting of silyl groups, halide atoms, nitro groups, amine groups, hydroxy groups, alkoxy groups, ether groups, aldehyde groups, ketone groups, ester groups, amide groups, and carboxylic acid groups:
• ##STR156## wherein R is a group that meets the definitions of both R.sub.1 and R'.sub.2 ##STR157## wherein R is a group that meets the definitions of both R.sub.1 and R'.sub.3 ##STR158## wherein R is a group that meets the definitions of both R.sub.1 and Ar' ##STR159## wherein R is a group that meets the definitions of both R.sub.2 and R'.sub.3 ##STR160## wherein R is a group that meets the definitions of both R.sub.2 and Ar' ##STR161## wherein R is a group that meets the definitions of both R.sub.3 and Ar' ##STR162## (b) those of the following formulae, wherein R.sub.1 and R'.sub.1 are each independently selected from the group consisting of hydrogen, alkyl, and substituted alkyl, R.sub.2 and R'.sub.2 are each independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, and substituted arylalkyl, Ar and Ar' are each independently selected from the group consisting of aryl, substituted aryl, arylalkyl, and substituted arylalkyl, and Y is selected from the group consisting of alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, and substituted arylalkyl, wherein the substituents on the substituted alkyl, substituted aryl, and substituted arylalkyl groups are selected from the group consisting of silyl groups, halide atoms, nitro groups, amine groups, hydroxy groups, alkoxy groups, ether groups, aldehyde groups, ketone groups, ester groups, amide groups, and carboxylic acid groups:
• ##STR163## wherein R is a group that meets the definitions of both Ar and R'.sub.1 ##STR164## wherein R is a group that meets the definitions of both Ar and R'.sub.2 ##STR165## wherein R is a group that meets the definitions of both R.sub.1 and R'.sub.2 ##STR166## (c) those of the following formulae, wherein R.sub.1 and R'.sub.1 are each independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, and substituted arylalkyl, R.sub.2 and R'.sub.2 are each independently selected from the group consisting of aryl, substituted aryl, arylalkyl, and substituted arylalkyl, Ar and Ar' are each independently selected from the group consisting of aryl, substituted aryl, arylalkyl, and substituted arylalkyl, and Y is selected from the group consisting of alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, and substituted arylalkyl, wherein the substituents on the substituted alkyl, substituted aryl, and substituted arylalkyl groups are selected from the group consisting of silyl groups, halide atoms, nitro groups, amine groups, hydroxy groups, alkoxy groups, ether groups, aldehyde groups, ketone groups, ester groups, and carboxylic acid groups:
• ##STR167## wherein R is a group that meets the definitions of both Ar and R'.sub.1 ##STR168## wherein R is a group that meets the definitions of both Ar and R'.sub.2 ##STR169## wherein R is a group that meets the definitions of both R.sub.1 and R'.sub.2 ##STR170## (d) those of the following formulae, wherein R.sub.1 is an electron withdrawing group, R.sub.2 is selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, and substituted arylalkyl, R3 is selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, and substituted arylalkyl, Ar is selected from the group consisting of aryl, substituted aryl, arylalkyl, and substituted arylalkyl, R'.sub.1 is selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, and substituted arylalkyl, R'.sub.2 is selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, and substituted arylalkyl, Ar' is selected from the group consisting of aryl, substituted aryl, arylalkyl, and substituted arylalkyl, and Z is selected from the group consisting of alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, and substituted arylalkyl, wherein the substituents on the substituted alkyl, substituted aryl, and substituted arylalkyl groups are selected from the group consisting of silyl groups, halide atoms, nitro groups, amine groups, hydroxy groups, alkoxy groups, ether groups, aldehyde groups, ketone groups, ester groups, amide groups, and carboxylic acid groups:
• ##STR171## wherein R is a group that meets the definitions of both R.sub.1 and Ar' ##STR172## wherein R is a group that meets the definitions of both R.sub.1 and R'.sub.1 ##STR173## wherein R is a group that meets the definitions of both R.sub.1 and R'.sub.2 ##STR174## wherein R is a group that meets the definitions of both R.sub.2 and Ar' ##STR175## wherein R is a group that meets the definitions of both R.sub.2 and R'.sub.1 ##STR176## wherein R is a group that meets the definitions of both R.sub.2 and R'.sub.2 ##STR177## wherein R is a group that meets the definitions of both R.sub.3 and Ar' ##STR178## wherein R is a group that meets the definitions of both R.sub.3 and R'.sub.1 ##STR179## wherein R is a group that meets the definitions of both R.sub.3 and R'.sub.2 ##STR180## wherein R is a group that meets the definitions of both Ar and Ar' ##STR181## wherein R is a group that meets the definitions of both Ar and R'.sub.1 ##STR182## wherein R is a group that meets the definitions of both Ar and R'.sub.2 ##STR183## and (e) mixtures thereof.