Solution of gallium phthalocyanine method for preparing the same method for producing gallium phthalocyanine crystal method for purifying composition containing gallium phthalocyanine and method for producing electrophotographic photosensitive member

Patent metadata

Field	Value
Publication number	US-9535345-B2
Application number	US-201514702546-A
Country	US
Kind code	B2
Filing date	May 1, 2015
Priority date	Jan 31, 2013
Publication date	Jan 3, 2017
Grant date	Jan 3, 2017

Abstract

A solution of a gallium phthalocyanine contains a compound of formula (1) and a gallium phthalocyanine of formula (2),

H 2 N—CH 2 —R 1 —CH 2 —NH 2   (1)

wherein R 1 represents a single bond, or a substituted or unsubstituted alkylene group having 1 to 10 main-chain carbon atoms, a substituent of the substituted alkylene group is an alkyl group having 1 to 3 carbon atoms, an alkyl group having 1 to 3 carbon atoms and being substituted with an amino group, or a hydroxy group, one of the carbon atoms in the main chain of the alkylene group may be replaced with an oxygen atom, a sulfur atom, or a bivalent group represented by the formula —NR 2 —, and R 2 represents a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, or an alkyl group having 1 to 3 carbon atoms and being substituted with an amino group, and

wherein X 1 represents a chlorine atom or hydroxy group.

First claim

What is claimed is:

1. A method for producing a gallium phthalocyanine crystal, comprising:
(a1) dissolving a gallium phthalocyanine represented by the formula (2) in a compound represented by the formula (1), to prepare a solution of a gallium phthalocyanine represented by the formula (2),

wherein, in the formula (2),
X 1 represents a chlorine atom or a hydroxy group
H 2 N—CH 2 —R 1 —CH 2 —NH 2   (1)

wherein, in the formula (1), R 1 represents a single bond, or a substituted or unsubstituted alkylene group having 1 to 10 main-chain carbon atoms,
a substituent of the substituted alkylene group is an alkyl group having 1 to 3 carbon atoms, an alkyl group having 1 to 3 carbon atoms and being substituted with an amino group, or a hydroxy group,
one of the carbon atoms in the main chain of the alkylene group may be replaced with an oxygen atom, a sulfur atom, or a bivalent group represented by the formula —NR 2 —, and
R 2 represents a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, or an alkyl group having 1 to 3 carbon atoms and being substituted with an amino group, and
(b1) mixing the solution prepared in the step (a1) with a poor solvent for the gallium phthalocyanine represented by the formula (2) to perform the crystal transformation of the gallium phthalocyanine represented by the formula (2), thereby forming a hydroxygallium phthalocyanine crystal having peaks at Bragg angles 2θ of 6.9°±0.3° and 26.6°±0.3° in X-ray diffraction with CuKα radiation or a hydroxygallium phthalocyanine crystal having peaks at Bragg angles 2θ of 7.4°±0.3° and 28.3°±0.3° in X-ray diffraction with CuKα radiation.

2. The method for producing a gallium phthalocyanine crystal according to claim 1 , wherein the poor solvent is an aprotic solvent having a solubility parameter value of 9 or more and 14 or less, and
the hydroxygallium phthalocyanine crystal prepared in the step (b1) is a hydroxygallium phthalocyanine crystal having peaks at Bragg angles 2θ of 7.4°±0.3° and 28.3°±0.3° in X-ray diffraction with CuKα radiation.

3. The method for producing a gallium phthalocyanine crystal according to claim 1 , wherein the poor solvent is an aprotic solvent having a solubility parameter value of less than 9 or more than 14, and
the hydroxygallium phthalocyanine crystal prepared in the step (b1) is a hydroxygallium phthalocyanine crystal having peaks at Bragg angles 2θ of 6.9°±0.3° and 26.6°±0.3° in X-ray diffraction with CuKα radiation.

4. A method for purifying a composition containing a gallium phthalocyanine, comprising:
(a2) mixing a compound represented by the formula (1) with a composition containing a gallium phthalocyanine represented by the formula (2) to prepare a solution; and
(b2) filtering the solution prepared in the step (a2) to purify the composition containing the gallium phthalocyanine represented by the formula (2),
H 2 N—CH 2 —R 1 —CH 2 —NH 2   (1)

wherein, in the formula (1),
R 1 represents a single bond, or a substituted or unsubstituted alkylene group having 1 to 10 main-chain carbon atoms,
a substituent of the substituted alkylene group is an alkyl group having 1 to 3 carbon atoms, an alkyl group having 1 to 3 carbon atoms and being substituted with an amino group, or a hydroxy group,
one of the carbon atoms in the main chain of the alkylene group may be replaced with an oxygen atom, a sulfur atom, or a bivalent group represented by the formula —NR 2 —, and
R 2 represents a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, or an alkyl group having 1 to 3 carbon atoms and being substituted with an amino group, and

wherein, in the formula (2),
X 1 represents a chlorine atom or a hydroxy group.

5. The method for purifying a composition containing a gallium phthalocyanine according to claim 4 , further comprising:
subjecting the solution prepared in the step (a2) to adsorption treatment between the step (a2) and the step (b2).

6. The method for purifying a composition containing a gallium phthalocyanine according to claim 4 , wherein the compound represented by the formula (1) is a compound represented by the formula (1a),
H 2 N—CH 2 —R 3 —CH 2 —NH 2   (1a)

wherein, in the formula (1a), R 3 represents a substituted or unsubstituted alkylene group having 1 to 3 main-chain carbon atoms, a substituent of the substituted alkylene group is an alkyl group having 1 or 2 carbon atoms or an alkyl group having 1 or 2 carbon atoms and being substituted with an amino group, one of the carbon atoms in the main chain of the alkylene group may be replaced with an oxygen atom, a sulfur atom, or a bivalent group represented by the formula —NR 4 —, and R 4 represents an alkyl group having 1 or 2 carbon atoms, or an alkyl group having 1 or 2 carbon atoms and being substituted with an amino group.

7. A method for producing an electrophotographic photosensitive member, comprising:
producing a hydroxygallium phthalocyanine crystal by the method according to claim 6 ; and
producing an electrophotographic photosensitive member by the use of the produced hydroxygallium phthalocyanine crystal.

8. The method for producing a gallium phthalocyanine crystal according to claim 3 ,
wherein the aprotic solvent having a solubility parameter value of 9 or more and 14 or less is N,N-dimethylformamide, tetrahydrofuran, acetone, 1,3-dioxolan, pyridine, N-methyl-2-pyrrolidone, acetonitrile, dimethyl sulfoxide, or γ-butyrolactone.

9. The method for producing a gallium phthalocyanine crystal according to claim 2 ,
wherein the aprotic solvent having a solubility parameter value of less than 9 or more than 14 is water, toluene, triethylamine, or propylene carbonate.

Assignees

• Canon Kk

Inventors

• Nishida Tsutomu
• Tanaka Masato
• Kawahara Masataka

Classifications

• G03G5/0662 Primary

  containing metal elements · CPC title

• G03G5/0696 Primary

  Phthalocyanines · CPC title

• C09B67/0083

  Solutions of dyes · CPC title

• G03C1/735

  Organo-metallic compounds · CPC title

• C09B67/0026

  of phthalocyanine pigments · CPC title