Method of producing gallium phthalocyanine crystal and method of producing electrophotographic photosensitive member using the method of producing gallium phthalocyanine crystal

• US 9,068,083 B2
• Filed: 11/29/2012
• Issued: 06/30/2015
• Est. Priority Date: 11/30/2011
• Status: Expired due to Fees

• Current Assignee: Canon Kabushiki Kaisha (Canon Inc.)
• Original Assignee: Canon Kabushiki Kaisha (Canon Inc.)
• Inventors: Tanaka, Masato, Kawahara, Masataka, Watariguchi, Kaname, Murakami, Takeshi, Yoshida, Akira
• Primary Examiner(s): Dote, Janis L
• Application Number:
  US13/688,880
• Publication Number:
  US 20130137032A1
• Time in Patent Office: 943 Days
• Field of Search: 540/141, 430/59.4, 430/78, 430/133
• US Class Current: 1/1
• CPC Class Codes: C09B 67/0002 Grinding; Milling with solid grinding or milling assistants
• CPC Class Codes: C09B 67/0016 of phthalocyanines
• CPC Class Codes: C09B 67/0026 of phthalocyanine pigments
• CPC Class Codes: G03G 5/0542 Polyvinylalcohol, polyallylalcohol; Derivatives thereof, e.g. polyvinylesters, polyvinylethers, polyvinylamines
• CPC Class Codes: G03G 5/0564 Polycarbonates
• CPC Class Codes: G03G 5/0696 Phthalocyanines
• CPC Class Codes: G03G 5/14756 Polycarbonates

Abstract

Provided is a method of producing an electrophotographic photosensitive member having improved sensitivity and capable of outputting an image having less image defects due to a ghost phenomenon not only under a normal-temperature, normal-humidity environment but also under a low-temperature, low-humidity environment as a particularly severe condition. The method of producing a gallium phthalocyanine crystal includes subjecting a gallium phthalocyanine and a specific amine compound, which are added to a solvent, to a milling treatment to perform crystal transformation of the gallium phthalocyanine. In addition, the gallium phthalocyanine crystal is used in the photosensitive layer of the electrophotographic photosensitive member.

Claims

1. A method of producing a gallium phthalocyanine crystal, comprising

providing a low-crystalline hydroxygallium phthalocyanine treated by an acid pasting method;

providing a dispersion by dispersing the low-crystalline hydroxygallium phthalocyanine and an amine compound represented by the following formula (1) into an amide solvent or a sulfoxide solvent, and

subjecting the dispersion to a milling treatment to conduct a crystal transformation of the low-crystalline hydroxygallium phthalocyanine, and obtaining a hydroxygallium phthalocyanine crystal containing the amine compound represented by the formula (1) in the crystal;

2. The method of producing a gallium phthalocyanine crystal according to claim 1, wherein at least one of R¹ to R¹⁰ represents an amino group substituted with a substituted or unsubstituted alkyl group.

3. The method of producing a gallium phthalocyanine crystal according to claim 2, wherein the substituted or unsubstituted alkyl group in the amino group substituted with the substituted or unsubstituted alkyl group comprises an alkyl group substituted with an alkoxy group, an alkyl group substituted with an aryl group, or an unsubstituted alkyl group.

4. The method of producing a gallium phthalocyanine crystal according to claim 3, wherein the amino group substituted with the substituted or unsubstituted alkyl group comprises a dialkylamino group.

5. The method of producing a gallium phthalocyanine crystal according to claim 4, wherein the dialkylamino group comprises a dimethylamino group or a diethylamino group.

6. The method of producing a gallium phthalocyanine crystal according to claim 5, wherein the amine compound comprises an amine compound represented by the following formula (2):

7. The method of producing a gallium phthalocyanine crystal according to claim 1, wherein at least one of R¹ to R¹⁰ represents a substituted or unsubstituted cyclic amino group.

8. The method of producing a gallium phthalocyanine crystal according to claim 7, wherein the substituted or unsubstituted cyclic amino group comprises a morpholino group or a 1-piperidino group.

9. The method of producing a gallium phthalocyanine crystal according to claim 8, wherein the amine compound comprises an amine compound represented by the following formula (3)

10. The method of producing a gallium phthalocyanine crystal according to claim 1, wherein the hydroxygallium phthalocyanine crystal comprises a hydroxygallium phthalocyanine crystal having peaks at Bragg angles 2θ

±

0.2°

of 7.4° and

28.3°

in CuKα

X-ray diffraction.

11. The method of producing a gallium phthalocyanine crystal according to claim 1, wherein the amide solvent comprises N,N-dimethylformamide and the sulfoxide solvent comprises dimethyl sulfoxide.

12. A method of producing an electrophotographic photosensitive member including an electric-conductive support, and a photosensitive layer formed on the electric-conductive support, the photosensitive layer containing a hydroxygallium phthalocyanine crystal, the method comprising:

producing the hydroxygallium phthalocyanine crystal by the production method according to claim 1;

preparing a mixed liquid comprising the hydroxygallium phthalocyanine crystal and a binder resin; and

applying the mixed liquid onto the electric-conductive support as a film and drying the resultant applied film to form the photosensitive layer.