Phosphorous-containing compounds as adjuvant for positive electrostatic liquid developers

Claim 2

An improved positive electrostatic liquid developer having improved charging characteristics consisting essentially of (A) a nonpolar liquid having a Kauributanol value of less than 30, present in a major amount, (B) thermoplastic resin particles having dispersed therein 0.1 to 10 percent by weight based on the total weight of developer solids of a phosphorous-containing compound which is substantially insoluble or immiscible in the nonpolar liquid at ambient temperatures and is selected from the group consisting of (1) polyphosphoric acids; (2) the +1 and +2 metal salts of said polyphosphoric acids; (3) phosphorous pentoxide; (4) pyrophosphate compounds of the general formula: ##STR10## wherein R and R', which can be the same or different are alkyl of 1 to 10 carbon atoms; (5) the +1 and +2 metal salts of said pyrophosphates; (6) phosphonic acids of the general formula: ##STR11## wherein R is alkyl of 1 to 30 carbon atoms and aryl of 6 to 30 carbon atoms, n is a whole number of 1 to 6; (7) the +1 and +2 metal salts of said phosphonic acids; (8) phosphate compounds of the general formula: ##STR12## wherein R and R', which can be the same or different, are H, alkyl of 1 to 30 carbon atoms and aryl of 6 to 30 carbon atoms, n is whole number of 1 to 6; and (9) the +1 and +2 metal salts of said phosphate compounds, the resin particles having an average by area particle size of less than 10 μm, and (C) a nonpolar liquid soluble ionic or zwitterionic charge director compound.

Claim 3

A positive, liquid electrostatic developer according to claim 1 wherein the phosphorous-containing compound is a polyphosphoric acid.

Claim 4

A positive, liquid electrostatic developer according to claim 1 wherein the phosphorous-containing compound is a +1 or +2 metal salt of a polyphosphoric acid.

Claim 5

A positive, liquid electrostatic developer according to claim 1 wherein the phosphorous-containing compound is phosphorous pentoxide.

Claim 6

A positive, liquid electrostatic developer according to claim 1 wherein the phosphorous-containing compound is of the general formula: ##STR13## wherein R is alkyl of 1 to 30 carbon atoms and aryl of 6 to 30 carbon atoms, and n is a whole number of 1 to 6.

Claim 7

A positive, liquid electrostatic developer according to claim 5 wherein the phosphorous-containing compound is n-dodecylphosphonic acid.

Claim 8

A positive liquid electrostatic developer according to claim 1 wherein the phosphorous-containing compound is of the general formula: ##STR14## wherein R and R', which can be the same or different, are H, alkyl of 1 to 30 carbon atoms and aryl of 6 to 30 carbon atoms, and n is a whole number of 1 to 6.

Claim 9

A positive, liquid electrostatic developer according to claim 1 wherein component (A) is present in 85 to 99.9% by weight, based on the total weight of liquid developer, the total weight of developer solids to 15.0% by weight, and component (C) is present in an amount of 0.1 to 10,000 mg/g developer solids.

Claim 10

A positive, liquid electrostatic developer according to claim 1 containing up to about 60 percent by weight of a colorant based on the total weight of developer solids.

Claim 11

A positive, liquid electrostatic developer according to claim 9 wherein the colorant is a pigment.

Claim 12

A positive, liquid electrostatic developer according to claim 1 wherein no colorant is present.

Claim 13

A positive, liquid electrostatic developer according to claim 1 wherein an additional compound is present which is an adjuvant selected from the group consisting of aminoalcohol, polybutylene succinimide, and aromatic hydrocarbon.

Claim 14

A positive, liquid electrostatic developer according to claim 9 wherein an additional compound is present which is an adjuvant selected from the group consisting of aminoalcohol, polybutylene succinimide, and an aromatic hydrocarbon.

Claim 15

A positive liquid electrostatic developer according to claim 13 wherein an aminoalcohol adjuvant compound is present.

Claim 16

A positive, liquid electrostatic developer according to claim 13 wherein a polybutylene succinimide adjuvant compound is present.

Claim 17

A positive, liquid electrostatic developer according to claim 13 wherein an aromatic hydrocarbon adjuvant compound is present.

Claim 18

A positive, liquid electrostatic developer according to claim 14 wherein the aminoalcohol adjuvant compound is triisopropanolamine.

Claim 19

A positive, liquid electrostatic developer according to claim 1 wherein the thermoplastic resin is a copolymer of ethylene and an alpha,betaethylenically unsaturated acid selected from the group consisting of acrylic acid and methacrylic acid.

Claim 20

A positive, liquid electrostatic developer according to claim 1 wherein the thermoplastic resin is a terpolymer of methylacrylate/methacrylic acid/ethylhexyl acrylate.

Claim 21

A positive, liquid electrostatic developer according to claim 1 wherein the thermoplastic resin is a copolymer of ethylene (80 to 99.9%)/acrylic or methacrylic acid (20 to 0%)/alkyl ester of acrylic or methacrylic acid wherein alkyl is 1 to 5 carbon atoms (0 to 20%).

Claim 22

A positive, liquid electrostatic developer according to claim 9 wherein the thermoplastic resin is a copolymer of ethylene (80 to 99.9%)/acrylic or methacrylic acid (20 to 0%)/alkyl ester of acrylic or methacrylic acid wherein alkyl is 1 to 5 carbon atoms (9 to 20%).

Claim 23

A positive, liquid electrostatic developer, according to claim 20 wherein the thermoplastic resin is a copolymer of ethylene (89%)/methacrylic acid (11%) having a melt index at 190° C. of 100.

Claim 24

A positive, liquid electrostatic developer according to claim 1 wherein the particles have an average by area particle size of less than 5 μm.

Claim 25

A positive, liquid electrostatic toner according to claim 1 wherein component (C) is an oil-soluble petroleum sulfonate.

Claim 26

A positive, liquid electrostatic toner according to claim 1 wherein component (C) is lecithin.

Claim 27

A process for preparing a positive, liquid electrostatic developer for electrostatic imaging comprising (A) dispersing at an elevated temperature in a vessel a thermoplastic resin, 0.1 to 10 percent by weight based on the total weight of developer solids of a phosphorous-containing compound which is substantially insoluble or immiscible in a nonpolar liquid at ambient temperatures as is selected from the group consisting of (1) polyphosphoric acids; (2) the +1 and +2 metal salts of said polyphosphoric acids; (3) phosphorous pentoxide; (4) pyrophosphate compounds of the general formula: ##STR15## wherein R and R', which can be the same or different are alkyl of 1 to 10 carbon atoms; (5) the +1 and +2 metal salts of said pyrophosphates; (6) phosphonic acids of the general formula: ##STR16## wherein R is alkyl of 1 to 30 carbon atoms and aryl of 6 to 30 carbon atoms, n is a whole number of 1 to 6; (7) the +1 and +2 metal salts of said phosphonic acids; (8) phosphate compounds of the general formula: ##STR17## wherein R and R', which can be the same or different, are H, alkyl of 1 to 30 carbon atoms and aryl of 6 to 30 carbon atoms, n is whole number of 1 to 6; and (9) the +1 and +2 metal salts of said phosphate compounds, a dispersant nonpolar liquid having a Kauri-butanol value of less than 30, and a colorant, while maintaining the temperature in the vessel at a temperature sufficient to plasticize and liquify the resin and below that at which the dispersant nonpolar liquid degrades and the resin and/or colorant decomposes, (B) cooling the dispersion, either (1) without stirring to form a gel or solid mass, followed by shredding the gel or solid mass and grinding by means of particulate media with or without the presence of additional liquid; (2) with stirring to form a viscous mixture and grinding by means of particulate with or without the presence of additional liquid; or (3) while grinding by means of particulate media to prevent the formation of a gel or solid mass with or without the presence of additional (C) separating the dispersion of thermoplastic toner particles having an average by area particle size of less than 10 μm from the particulate media, and (D) adding to the dispersion (during or subsequent to Step (A)) a nonpolar liquid soluble ionic or zwitterionic charge director compound.

Claim 28

A process for preparing a positive, liquid electrostatic developer for electrostatic imaging comprising (A) dispersing at an elevated temperature in a vessel a thermoplastic resin, 0.1 to 10 percent by weight based on the total weight of developer solids of a phosphorous-containing compound which is substantially insoluble or immiscible in a nonpolar liquid at ambient temperatures as is selected from the group consisting of (1) polyphosphoric acids; (2) the +1 and +2 metal salts of said polyphosphoric acids; (3) phosphorous pentoxide; (4) pyrophosphate compounds of the general formula: ##STR15## wherein R and R', which can be the same or different are alkyl of 1 to 10 carbon atoms; (5) the +1 and +2 metal salts of said pyrophosphates; (6) phosphonic acids of the general formula: ##STR16## wherein R is alkyl of 1 to 30 carbon atoms and aryl of 6 to 30 carbon atoms, n is a whole number of 1 to 6; (7) the +1 and +2 metal salts of said phosphonic acids; (8) phosphate compounds of the general formula: ##STR17## wherein R and R', which can be the same or different, are H, alkyl of 1 to 30 carbon atoms and aryl of 6 to 30 carbon atoms, n is whole number of 1 to 6; and (9) the +1 and +2 metal salts of said phosphate compounds, a dispersant nonpolar liquid having a Kauri-butanol value of less than 30, and a colorant, while maintaining the temperature in the vessel at a temperature sufficient to plasticize and liquify the resin and below that at which the dispersant nonpolar liquid degrades and the resin and/or colorant decomposes, (B) cooling the dispersion, either (1) without stirring to form a gel or solid mass, followed by shredding the gel or solid mass and grinding by means of particulate media with or without the presence of additional liquid; (2) with stirring to form a viscous mixture and grinding by means of particulate with or without the presence of additional liquid; or (3) while grinding by means of particulate media to prevent the formation of a gel or solid mass with or without the presence of additional (C) separating the dispersion of thermoplastic toner particles having an average by area particle size of less than 10 μm from the particulate media, and (D) adding to the dispersion (during or subsequent to Step (A)) a nonpolar liquid soluble ionic or zwitterionic charge director compound.

Claim 29

A process according to claim 26 wherein the phosphorous-containing compound is a polyphosphoric

Claim 30

A process according to claim 26 wherein the phosphorous-containing compound is a +1 or +2 metal salt of a polyphosphoric acid.

Claim 31

A process according to claim 26 wherein the phosphorous-containing compound is phosphorous pentoxide.

Claim 32

A process according to claim 26 wherein the phosphorous-containing compound is of the general formula: ##STR18## wherein R is alkyl of 1 to 30 carbon atoms and aryl of 6 to 30 carbon atoms, n is a whole number of 1 to 6.

Claim 33

A process according to claim 30 wherein the phosphorous-containing compound is n-dodecylphosphonic acid.

Claim 34

A process according to claim 26 wherein the phosphorous-containing compound is of the general formula: ##STR19## wherein R and R', which can be the same or different, are H, alkyl of 1 to 30 carbon atoms and aryl of 6 to 30 carbon atoms, n is a whole number of 1 to 6.

Claim 35

A process according to claim 26 wherein there is present in the vessel up to 100% by weight of a polar additive having a Kauri-butanol value of at least 30, the percentage based on the total weight of the liquid in the developer.

Claim 36

A process according to claim 26 wherein the particulate media are selected from the group consisting of stainless steel, carbon steel, ceramic, alumina, zirconium, silica and sillimanite.

Claim 37

A process according to claim 26 wherein the thermoplastic resin is a copolymer of ethylene and an alpha,beta-ethylenically unsaturated acid selected from the group consisting of acrylic acid and methacrylic acid.

Claim 38

A process according to claim 26 wherein the thermoplastic resin is a copolymer of ethylene (80 to 99.9%)/acrylic or methacrylic acid (20 to 0%)/alkyl ester of acrylic or methacrylic acid wherein alkyl is 1 to 5 carbon atoms (0 to 20%).

Claim 39

A process acording to claim 36 wherein the thermoplastic resin is a copolymer of ethylene (89%) methacrylic acid (11%) having a melt index at 190° C. of 100.

Claim 40

A process according to claim 26 wherein the ionic or zwitterionic compound is an oil-soluble petroleum sulfonate.

Claim 41

A process according to claim 26 wherein the ionic or zwitterionic compound is lecithin.

Claim 42

A process according to claim 26 wherein additional dispersant nonpolar liquid, polar liquid, or combinations thereof is present to reduce the concentration of toner particles to between 0.1 to 15 percent by weight with respect to the liquid.

Claim 43

A process according to claim 40 wherein the concentration of toner particles is reduced by additional dispersant nonpolar liquid.

Claim 44

A process according to claim 26 wherein cooling the dispersion is accomplished while grinding by means of particulate media to prevent the formation of a gel or solid mass with or without the presence of additional liquid.

Claim 45

A process according to claim 26 wherein cooling the dispersion is accomplished without stirring to form a gel or solid mass, followed by shredding the gel or solid mass and grinding by means of particulate media with or without the presence of additional liquid.

Claim 46

A process according to claim 26 wherein cooling the dispersion is accomplished with stirring to form a viscous mixture and grinding by means of particulate media with or without the presence of additional liquid.

Claim 47

A process according to claim 26 wherein an adjuvant compound selected from the group consisting of aminoalcohol, polybutylene succinimide, and an aromatic hydrocarbon is added.

Claim 48

A process according to claim 45 wherein the adjuvant compound is an aminoalcohol.

Claim 49

A process according to claim 46 wherein the aminoalcohol is triisopropanolamine.

Claim 50

A process according to claim 40 wherein an adjuvant compound selected from the group consisting of aminoalcohol, polybutylene succinimide, and an aromatic hydrocarbon is added to the liquid developer.

Claim 51

A process according to claim 26 wherein no colorant is present.

Claim 52

A process for preparing a positive liquid electrostatic developer for electrostatic imaging comprising (A) dispersing 0.1 to 10 percent by weight based on the total weight of developer solids of a phosphorous-containing compound which is substantially insoluble or immiscible in a nonpolar liquid at ambient temperatures and is selected from the group consisting of (1) polyphosphoric acids; (2) the +1 and +2 metal salts of said polyphosphoric acids; (3) phosphorous pentoxide; (4) pyrophosphate compounds of the general formula: ##STR20## wherein R and R', which can be the same or different are alkyl of 1 to 10 carbon atoms; (5) the +1 and +2 metal salts of said pyrophosphates; (6) phosphonic acids of the general formula: ##STR21## wherein R is alkyl of 1 to 30 carbon atoms and aryl of 6 to 30 carbon atoms, n is a whole number of 1 to 6; (7) the +1 and +2 metal salts of said phosphonic acids; (8) phosphate compounds of the general formula: ##STR22## wherein R and R', which can be the are H, alkyl of 1 to 30 carbon atoms and aryl of 6 to 30 carbon atoms, n is whole number of 1 to 6; and (9) the +1 and +2 metal salts of said phosphate compounds in a thermoplastic resin in the absence of a dispersant nonpolar liquid having a Kauri-butanol value of less than 30 to form a solid mass, (B) shredding the solid mass, (C) grinding the shredded solid mass by means of particulate media in the presence of a liquid selected from the group consisting of a polar liquid having a Kauri-butanol value of at least 30, a nonpolar liquid having a Kauri-butanol value of less than 30, and combinations thereof, thereby forming a dispersion of toner particles, (D) separating the dispersion of toner particles having an average by area particle size of less than 10 μm from the particulate media, and (E) adding additional nonpolar liquid, polar liquid or combinations thereof to reduce the concentration of toner particles to between 0.1 to 15.0 percent by weight with respect to the liquid; and (F) adding to the dispersion a liquid soluble ionic or zwitterionic compound.

Claim 53

A process for preparing a positive liquid electrostatic developer for electrostatic imaging comprising (A) dispersing 0.1 to 10 percent by weight based on the total weight of developer solids of a phosphorous-containing compound which is substantially insoluble or immiscible in a nonpolar liquid at ambient temperatures and is selected from the group consisting of (1) polyphosphoric acids; (2) the +1 and +2 metal salts of said polyphosphoric acids; (3) phosphorous pentoxide; (4) pyrophosphate compounds of the general formula: ##STR20## wherein R and R', which can be the same or different are alkyl of 1 to 10 carbon atoms; (5) the +1 and +2 metal salts of said pyrophosphates; (6) phosphonic acids of the general formula: ##STR21## wherein R is alkyl of 1 to 30 carbon atoms and aryl of 6 to 30 carbon atoms, n is a whole number of 1 to 6; (7) the +1 and +2 metal salts of said phosphonic acids; (8) phosphate compounds of the general formula: ##STR22## wherein R and R', which can be the are H, alkyl of 1 to 30 carbon atoms and aryl of 6 to 30 carbon atoms, n is whole number of 1 to 6; and (9) the +1 and +2 metal salts of said phosphate compounds in a thermoplastic resin in the absence of a dispersant nonpolar liquid having a Kauri-butanol value of less than 30 to form a solid mass, (B) shredding the solid mass, (C) grinding the shredded solid mass by means of particulate media in the presence of a liquid selected from the group consisting of a polar liquid having a Kauri-butanol value of at least 30, a nonpolar liquid having a Kauri-butanol value of less than 30, and combinations thereof, thereby forming a dispersion of toner particles, (D) separating the dispersion of toner particles having an average by area particle size of less than 10 μm from the particulate media, and (E) adding additional nonpolar liquid, polar liquid or combinations thereof to reduce the concentration of toner particles to between 0.1 to 15.0 percent by weight with respect to the liquid; and (F) adding to the dispersion a liquid soluble ionic or zwitterionic compound.

Claim 54

A process according to claim 50 wherein a colorant is present in step (A).

Claim 55

A process for preparing a positive, electrostatic liquid developer for electrostatic imaging comprising (A) dispersing 0.1 to 10 percent by weight based on the total weight of developer solids of a phosphorous-containing compound which is substantially insoluble or immiscible in a nonpolar liquid at ambient temperatures and is selected from the group consisting of (1) polyphosphoric acids; (2) the +1 and +2 metal salts of said polyphosphoric acids; (3) phosphorous pentoxide; (4) pyrophosphate compounds of the general formula: ##STR23## wherein R and R', which can be the same or different are alkyl of 1 to 10 carbon atoms; (5) the +1 and +2 metal salts of said pyrophosphates; (6) phosphonic acids of the general formula: ##STR24## wherein R is alkyl of 1 to 30 carbon atoms and aryl of 6 to 30 carbon atoms, n is a whole number of 1 to 6; (7) the +1 and +2 metal salts of said phosphonic acids; (8) phosphate compounds of the general formula: ##STR25## wherein R and R', which can be the same or different, are H, alkyl of 1 to 30 carbon atoms and aryl of 6 to 30 carbon atoms, n is whole number of 1 to 6; and (9) the +1 and +2 metal salts of said phosphate compounds in a thermoplastic resin in the absence of a dispersant nonpolar liquid having a Kauri-butanol value of less than 30 to form a solid mass, (B) shredding the solid mass, (C) redispersing the shredded solid mass at an elevated temperature in a vessel in the presence of a dispersant nonpolar liquid having a Kauri-butanol value of less than 30, while maintaining the temperature in the vessel at a temperature sufficient to plasticize and liquify the resin and below that at which the dispersant nonpolar liquid degrades and the resin decomposes, (D) cooling the dispersion, either (1) without stirring to form a gel or solid mass, followed by shredding the gel or solid mass and grinding by means of particulate media with or without the presence of additional liquid, (2) with stirring to form a viscous mixture and grinding by means of particulate media with or without the presence of additional liquid; or (3) while grinding by means of particulate media to prevent the formation of a gel or solid mass with or without the presence of additional liquid; (E) separating the dispersion of toner particles having an average by area particle size of less than 10 μm from the particulate media, and (F) adding additional nonpolar liquid, polar liquid or combinations thereof to reduce the concentration of toner particles to between 0.1 to 15.0 percent by weight with respect to the liquid; and (G) adding to the dispersion a liquid soluble ionic or zwitterionic compound.

Claim 56

A process for preparing a positive, electrostatic liquid developer for electrostatic imaging comprising (A) dispersing 0.1 to 10 percent by weight based on the total weight of developer solids of a phosphorous-containing compound which is substantially insoluble or immiscible in a nonpolar liquid at ambient temperatures and is selected from the group consisting of (1) polyphosphoric acids; (2) the +1 and +2 metal salts of said polyphosphoric acids; (3) phosphorous pentoxide; (4) pyrophosphate compounds of the general formula: ##STR23## wherein R and R', which can be the same or different are alkyl of 1 to 10 carbon atoms; (5) the +1 and +2 metal salts of said pyrophosphates; (6) phosphonic acids of the general formula: ##STR24## wherein R is alkyl of 1 to 30 carbon atoms and aryl of 6 to 30 carbon atoms, n is a whole number of 1 to 6; (7) the +1 and +2 metal salts of said phosphonic acids; (8) phosphate compounds of the general formula: ##STR25## wherein R and R', which can be the same or different, are H, alkyl of 1 to 30 carbon atoms and aryl of 6 to 30 carbon atoms, n is whole number of 1 to 6; and (9) the +1 and +2 metal salts of said phosphate compounds in a thermoplastic resin in the absence of a dispersant nonpolar liquid having a Kauri-butanol value of less than 30 to form a solid mass, (B) shredding the solid mass, (C) redispersing the shredded solid mass at an elevated temperature in a vessel in the presence of a dispersant nonpolar liquid having a Kauri-butanol value of less than 30, while maintaining the temperature in the vessel at a temperature sufficient to plasticize and liquify the resin and below that at which the dispersant nonpolar liquid degrades and the resin decomposes, (D) cooling the dispersion, either (1) without stirring to form a gel or solid mass, followed by shredding the gel or solid mass and grinding by means of particulate media with or without the presence of additional liquid, (2) with stirring to form a viscous mixture and grinding by means of particulate media with or without the presence of additional liquid; or (3) while grinding by means of particulate media to prevent the formation of a gel or solid mass with or without the presence of additional liquid; (E) separating the dispersion of toner particles having an average by area particle size of less than 10 μm from the particulate media, and (F) adding additional nonpolar liquid, polar liquid or combinations thereof to reduce the concentration of toner particles to between 0.1 to 15.0 percent by weight with respect to the liquid; and (G) adding to the dispersion a liquid soluble ionic or zwitterionic compound.

Claim 57

A process according to claim 52 wherein a colorant is present in step (C).