Method of preparing aqueous pigment dispersions
View Patent ↗A process for preparing an aqueous pigment dispersion is provided in which a pigment, a coating agent, a grinding agent and a vehicle are subjected to grinding, followed by removal of the grinding agent and the vehicle to form a press cake, and dispersing the press cake to form a pigment dispersion. Also disclosed is an ink-jet ink containing an aqueous vehicle and the aqueous pigment dispersion thus made.
1. A process for making an aqueous pigment dispersion comprising the steps of:
(a) grinding a mixture comprising a pigment, one or a combination of coating agents, a grinding agent and a vehicle, wherein said grinding agent is insoluble in said vehicle and soluble in water, and said coating agents contain an ionizable moiety and have a structure of formula (I):
Q M 1 ] n (I);
(b) washing with an aqueous medium to remove said grinding agent to form a press cake; and
(c) adding an aqueous vehicle, adjusting the pH to ionize said ionizable moiety on said coating agents, and dispersing said press cake from step (b), in this order or any other workable orders, to form a dispersion;
wherein each M 1 is COOH or NR 1 R 2 , or two M 1 groups can be taken together with the carbon atoms they are bonded to form a cyclic anhydride, or M 1 is OH when Q is C 6 -C 40 aryl; n is an integer from 2 to 6; each R 1 and R 2 is independently H, C 1 -C 9 alkyl or C 3 -C 12 cycloalkyl; and Q is C 6 -C 40 alkyl, C 6 -C 40 substituted alkyl, C 6 -C 40 aryl or Q is —Ar 1 —Y—Ar 2 — and forms a molecule of formula (II):
wherein Ar 1 and Ar 2 are independently C 6 -C 40 aryl; Y is CR 3 R 4 , S, S(O) or a straight bond; R 3 and R 4 are independently H or C 1 -C 9 alkyl; each M 2 is COOH, or two M 2 groups can be taken together with the carbon atoms they are bonded to form a cyclic anhydride; and each m is independently an integer from 2 to 4.
2. The process of claim 1 , further comprising a ultrafiltration step after step (c).
3. The process of claim 1 , wherein said grinding agent is an inorganic salt.
4. The process of claim 3 , wherein grinding takes place at temperature greater than 85° C.
5. The process of claim 4 , wherein grinding initially takes place at temperature greater than 85° C. and subsequently at temperature greater than 135° C.
6. The process of claim 4 , wherein grinding initially takes place at temperature greater than 160° C. and subsequently at temperature greater than 85° C.
7. The process of claim 4 , wherein said aqueous medium in step (b) has a conductivity of less than 100 micro-Siemens per centimeter.
8. The process of claim 7 , wherein M 1 is COOH and a base is used to adjust the pH.
9. The process of claim 7 , wherein M 1 is NR 1 R 2 and an acid is used to adjust the pH.
10. The process of claim 7 , wherein two M 1 groups are taken together with the carbon atoms they are bonded to form a cyclic anhydride.
11. The process of claim 7 , wherein said combination of coating agents comprises a first coating agent and a second coating agent, wherein said first coating agent has a structure of formula (I):
Q M 1 ] n (I);
and
said second coating agent has a structure of formula (II):
wherein Q is C 6 -C 40 alkyl, C 6 -C 40 substituted alkyl or C 6 -C 40 aryl; each M 1 is NR 1 R 2 ; and each M 2 is COOH.
12. The process of claim 11 , wherein the molar amount of said second coating agent is less than the molar amount of said first coating agent.
13. The process of claim 10 , wherein Q is C 6 -C 40 aryl.
14. The process of claim 13 , wherein n is 4.
15. The process of claim 10 , wherein Q is —Ar 1 —Y—Ar 2 —.
16. The process of claim 15 , wherein Ar 1 and Ar 2 are phenyl.
17. The process of claim 16 , wherein Y is a straight bond.
18. The process of claim 17 , wherein each m is 2.
19. A process for making a readily dispersible press cake comprising the steps of:
(a) grinding a mixture comprising a pigment, one or a combination of coating agents, a grinding agent and a vehicle, wherein said grinding agent is insoluble in said vehicle and soluble in water, and said coating agents contain an ionizable moiety and have a structure of formula (I):
Q M 1 ] n (I);
and
(b) washing with an aqueous medium to remove said grinding agent to form a press cake;
wherein each M 1 is COOH or NR 1 R 2 , or two M 1 groups can be taken together with the carbon atoms they are bonded to form a cyclic anhydride, or M 1 is OH when Q is C 6 -C 40 aryl; n is an integer from 2 to 6; each R 1 and R 2 is independently H, C 1 -C 9 alkyl or C 3 -C 12 cycloalkyl; and Q is C 6 -C 40 alkyl, C 6 -C 40 substituted alkyl, C 6 -C 40 aryl or Q is —Ar 1 —Y—Ar 2 — and forms a molecule of formula (II):
wherein Ar 1 and Ar 2 are independently C 6 -C 40 aryl; Y is CR 3 R 4 , S, S(O) or a straight bond; R 3 and R 4 are independently h or C 1 -C 9 alkyl; each M 2 is COOH, or two M 2 groups can be taken together with the carbon atoms they are bonded to form a cyclic anhydride; and each m is independently an integer from 2 to 4.
20. An ink-jet ink comprising an aqueous ink-jet vehicle and an aqueous pigment dispersion, where said aqueous pigment dispersion is prepared by a process comprising the steps of:
(a) grinding a mixture comprising a pigment, one or a combination of coating agents, a grinding agent and a vehicle, wherein said grinding agent is insoluble in said vehicle and soluble in water, and said coating agents contain an ionizable moiety and have a structure of formula (I):
Q M 1 ] n (I);
(b) washing with an aqueous medium to remove said grinding agent to form a press cake; and
(c) adding an aqueous vehicle, adjusting the pH to ionize said ionizable moiety on said coating agents, and dispersing said press cake from step (b), in this order or any other workable orders, to form a dispersion;
wherein each M 1 is COOH or NR 1 R 2 , or two M 1 groups can be taken together with the carbon atoms they are bonded to form a cyclic anhydride, or M 1 is OH when Q is C 6 -C 40 aryl; n is an integer from 2 to 6; each R 1 and R 2 is independently H, C 1 -C 9 alkyl or C 3 -C 12 cycloalkyl; and Q is C 6 -C 40 alkyl, C 6 -C 40 substituted alkyl, C 6 -C 40 aryl or Q is —Ar 1 —Y—Ar 2 — and forms a molecule of formula (II):
wherein Ar 1 and Ar 2 are independently C 6 -C 40 aryl; Y is CR 3 R 4 , S, S(O) or a straight bond; R 3 and R 4 are independently H or C 1 -C 9 alkyl; each M 2 is COOH, or two M 2 groups can be taken together with the carbon atoms they are bonded to form a cyclic anhydride; and each m is independently an integer from 2 to 4.