Dry toner of polymerization type for electronic photography

• US 6,383,702 B1
• Filed: 10/13/2000
• Issued: 05/07/2002
• Est. Priority Date: 10/13/1999
• Status: Expired due to Fees

• Current Assignee: Samsung Electronics Co. Ltd.
• Original Assignee: Samsung Electronics Co. Ltd.
• Inventors: Kim, Soon-Nam, Hong, Soon-Gil, Park, Moon-Soo, Ryu, Seung-Min, Eun, Jong-Moon, Jung, Hee-Won, Jang, Seung-Soon
• Primary Examiner(s): GOODROW, JOHN L
• Application Number:
  US09/689,742
• Time in Patent Office: 571 Days
• Field of Search: 430/108.3, 430/108.1, 430/137.15
• US Class Current: 430/108.1
• 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 9/08702 comprising macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
• CPC Class Codes: G03G 9/08704 Polyalkenes
• CPC Class Codes: G03G 9/08711 with esters of acrylic or methacrylic acid
• CPC Class Codes: G03G 9/08773 Polymers having silicon in the main chain, with or without sulfur, oxygen, nitrogen or carbon only
• CPC Class Codes: G03G 9/08782 Waxes

Abstract

A dry toner of polymerization type for electronic photography for forming an image on a recordable medium is synthesized during a polymerization process by adding a hydrophobic silica system compound having both hydrophobic groups and hydrophilic groups and having the following chemical structure formula:

the silica system compound being a stabilizer in a polymerization composition.

Claims

1. A toner, comprising:

a thermoplastic resin prepared from a solution including;

a stabilizer comprising a silicon compound, said silicon compound comprising a first structural unit of structural formula

 

a second structural unit of structural formula

 

and a third structural unit of structural formula

were R1 and R2 are independently selected from the group consisting essentially of an aliphatic compound of C₁ to C₃₀, an aliphatic compound of C₁ to C₃₀ including at least one functional group (G), a heteroaliphatic compound of C₁ to C₃₀, a heteroaliphatic compound of C₁ to C₃₀ including at least one functional group (G), a cycloaliphatic compound, a cycloaliphatic compound including at least one functional group (G), a heterocyclic aliphatic compound of C₁ to C₃₀, a heterocyclic aliphatic compound of C₁ to C₃₀ including at least one functional group (G), an aromatic compound of C₁ to C₃₀, and an aromatic compound including at least one functional group (G);

where G is selected from the group consisting essentially of amide (—

CONH—

), imine (—

CH═

N—

), amidino (—

N(NH₂)₂), amine (—

NRH, where R is an alkyl group), hydrazine (—

NHNH₂), hydrazone (—

N═

NH), halide, hydroxy, nitro (—

NO₂), cyano (—

CN), thiocyano (—

SCN), thiol (—

SH), carboxylic acid (—

COOH), carboxylate salt (COO—

M⁺, where M is an alkali metal), sulfonic (SO₃H), alkali sulfonate acid(SO₃—

M⁺), phosphoric acid(—

OPO₃H₂), and alkali salt of phosphate (—

OPO₃H—

M⁺);

said silicon compound being a three-dimensional network structure of cross-linking of said first structural unit, said second structural unit and said third structural unit of said silicon compound; and

a thermoplastic resin monomer.

2. The toner of claim 1, further comprised of said first structural unit and said second structural unit both being of structural formula

3. The toner of claim 1, further comprised of said thermoplastic resin monomer selected from the group consisting essentially of styrene, α

-methylstyrene, acrylic acid, methacrylic acid and methacrylic acid derivatives.

4. The toner of claim 2, further comprised of said thermoplastic resin monomer selected from the group consisting essentially of styrene, α

-methylstyrene, acrylic acid, methacrylic acid and methacrylic acid derivatives.

5. The toner of claim 4, further comprised of said thermoplastic resin being a polymer formed from styrene and butyl methacrylate.

6. The toner of claim 1, further comprised of a mole ratio of said first structural unit plus said second structural unit to said third structural unit in said silicon compound being greater than 6:

4.

7. The toner of claim 2, further comprised of a mole ratio of said first structural unit and said second structural unit to said third structural unit in said silicon compound being 7:

3.

8. The toner of claim 1, further comprising:

a coloring pigment.

9. The toner of claim 2, further comprising:

a coloring pigment.

33. The toner of claim 1, said solution further comprised of said silicon compound being at a concentration in a range of from 0.1 to 2% by weight in said solution.

34. The toner of claim 1, said solution further comprised of said thermoplastic resin monomer being in a range of from 15 to 30% by weight in said solution.

35. The toner of claim 1, said solution further comprising a solvent which is in a range of from 51.5 to 78.8% by weight of said solution.

36. The toner of claim 35, further comprised of:

said solvent being water; and

said solution further comprising one of an acidic solution or an alkaline solution which is in a range of from 0.1 to 10% by weight of said water.

37. The toner of claim 1, said solution further comprising a polymerization initiator.

38. The toner of claim 37, further comprised of said polymerization initiator being in a range of approximately from 0.1 to 2% by weight of said solution.

39. The toner of claim 1, said solution further comprising a charge control agent.

40. The toner of claim 39, further comprised of said charge control agent being in a range of approximately from 1 to 4% by weight of said solution.

41. The toner of claim 1, said solution further comprising a release agent.

42. The toner of claim 41, further comprised of said release agent being a wax group release agent which is in a range of approximately from 0.1 to 0.5% by weight of said solution.

43. The toner of claim 8, further comprised of a concentration of said coloring pigment being in a range of from 5 to 10% by weight of said solution.

10. A method of making a toner, comprising the steps of:

preparing a solution comprising;

a thermoplastic resin monomer;

a stabilizer comprising a silicon compound, said silicon compound comprising a first structural unit of structural formula

 

a second structural unit of structural formula

 

and a third structural unit of structural formula

where R1 and R2 are independently selected from the group consisting essentially of an aliphatic compound of C₁ to C₃₀, an aliphatic compound of C₁ to C₃₀ including at least one functional group (G), a heteroaliphatic compound of C₁ to C₃₀, a heteroaliphatic compound of C₁ to C₃₀ including at least one functional group (G), a cycloaliphatic compound, a cycloaliphatic compound including at least one functional group (G), a heterocyclic aliphatic compound of C₁ to C₃₀, a heterocyclic aliphatic compound of C₁ to C₃₀ including at least one functional group (G), an aromatic compound of C₁ to C₃₀, and an aromatic compound including at least one functional group (G);

where G is selected from the group consisting essentially of amide (—

CONH—

), imine (—

CH═

N—

), amidino (—

N(NH₂)₂), amine (—

NRH, where R is an alkyl group), hydrazine (—

NHNH₂), hydrazone (—

N═

NH), halide, hydroxy, nitro (—

NO₂), cyano (—

CN), thiocyano (—

SCN), thiol (—

SH), carboxylic acid (—

COOH), carboxylate salt (COO—

M⁺, where M is an alkali metal), sulfonic (SO₃H), alkali sulfonate acid(SO₃—

M⁺), phosphoric acid(—

OPO₃H₂), and alkali salt of phosphate (—

OPO₃H—

M⁺);

said silicon compound being a three-dimensional network structure of cross-linking of said first structural unit, said second structural unit and said third structural unit of said silicon compound; and

a coloring pigment; and

polymerizing said thermoplastic resin monomer in said solution to form toner particles.

11. The method of claim 10, further comprised of said silicon compound being at a concentration in a range of from 0.1 to 2% by weight in said solution.

12. The method of claim 10, further comprised of a mole ratio of said first structural unit plus said second structural unit to said third structural unit in said silicon compound being greater than 6:

4.

13. The method of claim 10, further comprised of said thermoplastic resin monomer being in a range of from 15 to 30% by weight in said solution.

14. The method of claim 10, further comprised of said solution further comprising a solvent which is in a range of from 51.5 to 78.8% by weight of said solution.

15. The method of claim 14, further comprised of said solvent being a solution in a range of from 0.1 to 10% by weight of one of an acidic compound or an alkaline compound in water.

16. The method of claim 10, further comprised of a concentration of said coloring pigment being in a range of from 5 to 10% by weight of said solution.

17. The method of claim 10, further comprised of said solution further comprising a polymerization initiator.

18. The method of claim 17, further comprised of said polymerization initiator being in a range of approximately from 0.1 to 2% by weight of said solution.

19. The method of claim 10, further comprised of said solution further comprising a charge control agent.

20. The method of claim 19, further comprised of said charge control agent being in a range of approximately from 1 to 4% by weight of said solution.

21. The method of claim 10, further comprised of said solution further comprising a wax group release agent.

22. The method of claim 21, further comprised of said wax group release agent being in a range of approximately from 0.1 to 0.5% by weight of said solution.

23. The method of claim 10, further comprised of said first structural unit and said second structural unit both being of structural formula

24. The method of claim 10, further comprised of said thermoplastic resin monomer being selected from the group consisting essentially of styrene, α

-methylstyrene, acrylic acid, methacrylic acid and methacrylic acid derivatives.

25. The method of claim 23, further comprised of said solution comprising styrene and butyl methacrylate.

26. The method of claim 10, further comprised of said step of preparing said solution further comprising the steps of:

dispersing said silicon compound in an alkaline aqueous solution to form a dispersion of said silicon compound;

then

dispersing said thermoplastic resin monomer in said dispersion of said silicon compound; and

then

adding said coloring pigment to said dispersion of said silicon compound including said thermoplastic resin monomer.

27. The method of claim 10, further comprised of said step of polymerizing said thermoplastic resin monomer further comprising the step of:

stirring said solution under nitrogen at a temperature of approximately 50°

C.

28. The method of claim 10, further comprising the step of:

separating and drying said toner particles.

29. The method of claim 10, further comprised of said coloring pigment being carbon black.

30. Toner particles prepared by the method of claim 10.

31. Toner particles prepared by the method of claim 23.

32. Toner particles prepared by the method of claim 25.