Method for forming toner particles having controlled morphology and containing a quaternary ammonium tetraphenylborate and a polymeric phosphonium salt

• US 6,416,921 B1
• Filed: 03/22/2001
• Issued: 07/09/2002
• Est. Priority Date: 03/22/2001
• Status: Expired due to Fees

• Current Assignee: Eastman Kodak Company
• Original Assignee: Heidelberg Digital LLC (Eastman Kodak Company)
• Inventors: McGrath, Gretchen S., Wilson, John C., Ezenyilimba, Matthew C.
• Primary Examiner(s): Rodee, Christopher
• Application Number:
  US09/814,923
• Time in Patent Office: 474 Days
• Field of Search: 430/137.14, 430/137.1, 523/339
• US Class Current: 430/137.14
• CPC Class Codes: G03G 9/0804 whereby the components are brought together in a liquid dispersing medium
• CPC Class Codes: G03G 9/0806 whereby chemical synthesis of at least one of the toner components takes place
• CPC Class Codes: G03G 9/0827 characterised by their shape, e.g. degree of sphericity

Abstract

A process for forming non-spherical toner particles by limited coalescence comprises: forming an organic phase comprising a polymeric material, a pigment, a quaternary ammonium tetraphenylborate salt, a phosphonium salt polymer formed by condensation of at least one dicarboxylic acid or dicarboxylic ester monomer with at least one diol monomer, at least one of the acid or ester monomers including a triarylphosphonium salt group, and a water-immiscible liquid; dispersing the organic phase in an aqueous phase containing a solid colloidal stabilizer; forming a suspension of small droplets of the organic phase in the aqueous phase by high shear agitation; removing the water-immiscible liquid from the small droplets, thereby forming a suspension of small solid particles in the aqueous phase; and separating and drying the solid particles, which are toner particles having a non-spherical shape.

Claims

1. A process for forming non-spherical toner particles by limited coalescence, said process comprising:

forming an organic phase comprising a polymeric material, a pigment, a quaternary ammonium tetraphenylborate salt, a phosphonium salt polymer formed by condensation of at least one dicarboxylic acid or dicarboxylic ester monomer with at least one diol monomer, at least one of said acid or ester monomers including a triarylphosphonium salt group, and a water-immiscible liquid;

dispersing said organic phase in an aqueous phase containing a solid colloidal stabilizer;

forming a suspension of small droplets of said organic phase in said aqueous phase by high shear agitation;

removing said water-immiscible liquid from said small droplets, thereby forming a suspension of small solid particles in said aqueous phase; and

separating said solid particles from said aqueous phase and drying said particles, thereby forming toner particles having a non-spherical shape.

2. The process of claim 1 wherein said quaternary ammonium tetraphenyl-borate salt is selected from the group consisting of salts represented by the general formulas (I), (II), and (III), and mixtures thereof:

wherein R¹ represents a substituted or unsubstituted alkyl or aryl group;

R² represents an alkylene or arylene group;

R₃, R₄, and R⁵ independently represent a substituted or unsubstituted alkyl group, and R³ and R⁴ taken together may represent a cyclic ring system; and

R⁶ represents hydrogen or an alkyl group;

wherein R¹ represents a substituted or unsubstituted alkyl or aryl group;

R² represents an alkylene or arylene group;

R³, R⁴ and R⁵ each independently represents a substituted or unsubstituted alkyl group; and

R³ and R⁴ taken together may represent a cyclic ring system;

wherein R¹, R², R³ and R⁴ each independently represents an alkyl or substituted alkyl group, and R¹ and R² taken together may represent a cyclic ring system.

3. The process of claim 2 wherein, in general formula (I), R¹ is selected from the group consisting of methyl, ethyl, n-propyl, n-butyl, n-hexyl, n-undecyl, n-heptadecyl, phenyl, 4-methylphenyl, and 4-t-butylphenyl;

R₂ is selected from the group consisting of ethylene, 1,3-propylene, 1,4-butylene, hexamethylene, and p-phenylene;

R³, R⁴, and R⁵ are each independently selected from the group consisting of methyl, ethyl, propyl, octadecyl, and benzyl, and R³ and R⁴ taken together may be 1,4-butylene or 1,5-pentylene, and R⁶ is selected from the group consisting of hydrogen, methyl, ethyl, n-propyl, n-butyl, octadecyl, and benzyl.

4. The process of claim 3 wherein R¹ is n-undecyl, R² is 1,3-propylene, R³ and R₄ are each methyl, R⁵ is benzyl, and R⁶ is hydrogen.

5. The process of claim 2 wherein, in general formula (II), R¹ is selected from the group consisting of methyl, ethyl, n-propyl, n-butyl, n-hexyl, n-undecyl, n-heptadecyl, phenyl, 4-methylphenyl, and 4-t-butylphenyl;

R² is selected from the group consisting of ethylene, 1,3-propylene, 1,4-butylene, hexamethylene, and p-phenylene;

R³, R⁴ and R⁵ are each independently selected from the group consisting of methyl, ethyl, propyl, octadecyl, and benzyl, and and R³ and R⁴ taken together may be 1,4-butylene or 1,5-pentylene.

6. The process of claim 5 wherein R¹ is n-undecyl or phenyl, R² is 1,3are each methyl, and R⁵ is benzyl.

7. The process of claim 2 wherein, in general formula (III), R¹, R², R³ and R⁴ are each independently selected from the group consisting of methyl, ethyl, propyl, isopropyl, n-butyl, t-butyl, pentyl, hexyl, 2-ethylhexyl, heptyl, octyl, decyl, octadecyl, benzyl, and 2-naphthylmethyl, and R¹ and R² taken together may be 1,4-butylene or 1,5-pentylene.

8. The process of claim 7 wherein R¹ and R² are each methyl, R³ is octadecyl, and R⁴ is 2-naphthylmethyl.

9. The process of claim 1 wherein said quaternary ammonium tetraphenyl-borate salt is selected from the group of salts listed in Tables 1, 2, and 3 following.

10. The process of claim 1 wherein said quaternary ammonium tetraphenylborate salt comprises about 0.1 to about 10 weight percent of total solids.

11. The process of claim 10 wherein said quaternary ammonium tetraphenylborate salt comprises about 0.5 to about 5 weight percent of total solids.

12. The process of claim 1 wherein said pigment comprises a dispersion.

13. The process of claim 1 wherein said water-immiscible liquid is selected from the group consisting of dichloromethane, ethyl acetate, methyl ethyl ketone, and mixtures thereof.

14. The process of claim 1 wherein said solid colloidal stabilizer comprises silicon dioxide.

15. The process of claim 1 wherein said aqueous phase has a pH of about 2 to about 7.

16. The process of claim 15 wherein said aqueous phase has a pH buffered to about 4.

17. The process of claim 1 wherein said phosphonium salt polymer is a condensation polymer of at least one dicarboxylic acid or dicarboxylic ester monomer with at least one diol monomer, at least one said acid or ester monomer including a triarylphosphonium salt group, said polymer having the general formula (IV)

wherein R¹ represents a substituted or unsubstituted alkylene group, a substituted or unsubstituted 1,2-ethenyl group, or a substituted or unsubstituted arylene group;

R₂ represents a substituted or unsubstituted alkylene group or a substituted or unsubstituted arylene group; and

R³ represents a substituted or unsubstituted alkyl group;

X⁻

represents an anion;

m and n are mole percents totaling 100, based on total diacid or diester, m having a value of 0.01 to 100; and

—

O—

R²—

O—

represents the radical of at least one diol monomer having a total mole percent, w, of 100, based on total diol.

18. The process of claim 17 wherein R¹ is selected from the group consisting of ethylene, 1,3-propylene, 1,4-butylene, p-phenylene, m-phenylene, 1,2-ethenyl, and 2,6-naphthalenyl.

19. The process of claim 17 wherein R² is is selected from the group consisting of ethylene, 1,2-propylene, 1,4-butylene, 2,2-dimethyl-1,3-propylene, 1,4-cyclohexylenedimethylene, 2,2,4,4-tetramethyl-1,3-cyclobutylene, 4,4′

-isopropylidenediphenylenepolyoxyalkylene, and p-phenylenepolyoxyalkylene.

20. The process of claim 17 wherein X⁻

is selected from the group consisting of tosylate, halide, tetraphenylborate, methosulfate, and triflate.

21. The process of claim 17 wherein R¹ is 1,2-ethenyl, R² is 4,4′

-isopropylidenediphenylene(2.0)oxypropylene, R³ is methyl, and X⁻

is tosylate.

22. The process of claim 17 wherein m is 10, n is 90, and w is 100.

23. The process of claim 1 wherein said phosphonium salt polymer comprises about 0.1 to about 10 weight percent of total solids.

24. The process of claim 23 wherein said phosphonium salt polymer comprises about 0.5 to about 5 weight percent of total solids.