JP2001005230A - Charge control agent for electrostatic charge image developing toner - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a charge control agent having improved high stability. SOLUTION: The charge control agent for electrostatic charge image developing toner uses a compound expressed by general formula 1 (in the formula, R represents a (substituted) alkyl group, a (substituted) aryl group or a (substituted) alalkyl group, R' represents hydrogen atom, an alkyl group, an aryl group or an alalkyl group, each of X1 and X2 represents hydrogen atom, a (substituted) alkyl group, a (substituted) aryl group, a (substituted) alkoxy group, a (substituted) alalkyl group or halogen atom, M represents hydrogen ion or metallic ion, (n) represents integers of 1-3 corresponding to the valency of M and (x) represents 0:15).

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an electrostatic charge developing toner used for electrophotography, electrostatic recording and the like, and more particularly to a charge control agent contained in the electrostatic charge developing toner.

[0002]

2. Description of the Related Art Conventionally, dry developing methods and wet developing methods have been known as developing methods used for electrophotography and the like. In the toner used in the dry development method, sufficient charge characteristics cannot be obtained only by dispersing the dye and pigment in the binder resin.
An appropriate amount of a charge control agent (charge control agent) is used.

As a conventional charge control agent, a nigrosine dye, an azine dye, a quaternary ammonium salt or the like is used to give a positive charge to the toner, and a metal salt of monoazo dye, salicylic acid, naphthoe is used to give a negative charge to the toner. Metal salts of acids and the like are known. Among them, the dye-based charge control agent is colored as its name implies, and it is extremely difficult to use it for a color toner. In many cases, the metal salt of salicylic acid is colorless or has a light color that does not cause a practical problem, and is therefore often used for a color toner.

As a toner using salicylic acid or a metal salt of a salicylic acid derivative, a chromium salicylate compound disclosed in JP-B-55-42752 is disclosed in
JP-A-37065 and JP-A-64-10261 disclose aluminum salicylate compounds.
255, JP-A-63-2074, JP-A-62-274
JP-A-3-33755 discloses a zinc salicylate compound.

[0005]

The toner using the above-mentioned metal compound of salicylic acid or a salicylic acid derivative as a charge control agent has a problem in stability against a change in use environment, particularly a change in humidity, and has a more stable charge control. The development of agents has been strongly desired.

[0006]

The present inventors have conducted intensive studies to solve the above problems, and as a result, have found that a series of compounds represented by the general formula (1) have stable charging ability. Reached.

That is, the present invention provides a compound represented by the general formula (1):

Embedded image (Wherein, R represents an alkyl group which may have a substituent, an aryl group which may have a substituent, or an aralkyl group which may have a substituent, and R ′ is a hydrogen atom, an alkyl group, X1 and X2 represent a hydrogen atom, an alkyl group optionally having a substituent, an aryl group optionally having a substituent, an alkoxy group optionally having a substituent, a substituent Represents an aralkyl group or a halogen atom, which may have, M represents a hydrogen ion or a metal ion, n represents an integer of 1 to 3 corresponding to the valence of M, and x
Represents a compound represented by formula (1), wherein X1 and X2 are hydrogen atoms, and R ′ is a hydrogen atom. , M is a charge control agent for a toner for electrostatic charge development, wherein M is a hydrogen ion, a zinc ion, an aluminum ion, a calcium ion, a barium ion or an iron ion.

[0008]

BEST MODE FOR CARRYING OUT THE INVENTION The salicylic acid derivative and its metal salt used in the present invention have a general formula (1) in which X1 and X2 each represent a hydrogen atom, an alkyl group which may have a substituent, or a substituent. Represents an aryl group which may be substituted, an alkoxy group which may have a substituent, an aralkyl group which may have a substituent or a halogen atom, preferably a hydrogen atom, a methyl group, an ethyl group, a propyl group, an isopropyl group, Butyl group, isobutyl group, sec-butyl group, t-butyl group,
Pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, linear alkyl group having 1 to 20 carbon atoms such as dodecyl group, aralkyl group such as benzyl group, phenethyl group, cyclopentyl group, cyclohexyl Group, a methylcyclohexyl group, a cycloheptyl group, a cyclic alkyl group having 1 to 12 carbon atoms such as a cyclooctyl group,
A phenyl group, a phenyl group having a substituent, an aryl group such as a naphthyl group, a methoxy group, an ethoxy group, a propoxy group, a chain alkoxy group having 1 to 20 carbon atoms such as a butoxy group, a fluorine atom, a chlorine atom, and a bromine atom. And more preferably a hydrogen atom, an alkyl group having 1 to 4 carbon atoms such as a methyl group, an ethyl group, a propyl group and a butyl group, a cyclohexyl group, a benzyl group and a phenyl group, and particularly preferably a hydrogen atom.

R represents an alkyl group which may have a substituent, an aryl group which may have a substituent or an aralkyl group which may have a substituent, and is preferably a methyl group, an ethyl group or a propyl group. , Isopropyl group, butyl group, isobutyl group, sec-butyl group, t-butyl group, pentyl group,
Hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, linear alkyl group having 1 to 20 carbon atoms such as dodecyl group, fluoromethyl group, difluoromethyl group, trifluoromethyl group, chloromethyl group, Dichloromethyl group, trichloromethyl group, trifluoroethyl group, hydroxyethyl group, chain alkyl group having a substituent such as aminoethyl group, benzyl group, aralkyl group such as phenethyl group, cyclopentyl group, cyclohexyl group,
A methylcyclohexyl group, a cycloheptyl group, a cyclic alkyl group having 1 to 12 carbon atoms such as a cyclooctyl group, a phenyl group, an aryl group such as a naphthyl group, a chlorophenyl group,
An aryl group having a substituent such as a fluorophenyl group and a bromophenyl group.

R 'represents a hydrogen atom, an alkyl group which may have a substituent, an aryl group which may have a substituent or an aralkyl group which may have a substituent, and is preferably a hydrogen atom, methyl Group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, t-
C1-C20 chain alkyl groups such as butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, fluoromethyl, difluoromethyl, trifluoromethyl Group, chloromethyl group, dichloromethyl group, trichloromethyl group, trifluoroethyl group, hydroxyalkyl group, chain alkyl group having a substituent such as aminoethyl group, benzyl group, aralkyl group such as phenethyl group, cyclopentyl group, C1-C12 cyclic alkyl groups such as cyclohexyl group, methylcyclohexyl group, cycloheptyl group, and cyclooctyl group; aryl groups such as phenyl group and naphthyl group; substituents such as chlorophenyl group, fluorophenyl group and bromophenyl group. And more preferably an aryl group having Is hydrogen atom, a methyl group, an ethyl group, a propyl group, an alkyl group having 1 to 4 carbon atoms such as butyl group, a cyclohexyl group, a benzyl group, a phenyl group, a hydrogen atom is particularly preferable.

M represents a hydrogen ion or a metal ion, preferably a hydrogen ion, calcium ion, barium ion, iron ion, nickel ion, cobalt ion, aluminum ion, zinc ion, magnesium ion, chromium ion, copper ion, manganese ion. , Titanium ion, more preferably hydrogen ion, calcium ion, barium ion, iron ion, aluminum ion,
Zinc ions, magnesium ions, and chromium ions.

The general formula (1) used in the present invention

Embedded image (Wherein, R represents an alkyl group which may have a substituent, an aryl group which may have a substituent, or an aralkyl group which may have a substituent, and R ′ is a hydrogen atom, an alkyl group, X1 and X2 represent a hydrogen atom, an alkyl group optionally having a substituent, an aryl group optionally having a substituent, an alkoxy group optionally having a substituent, a substituent Represents an aralkyl group or a halogen atom, which may have, M represents a hydrogen ion or a metal ion, n represents an integer of 1 to 3 corresponding to the valence of M, and x
The compound represented by 0 to 15) can be exemplified by the following salicylic acid derivatives and metal salts thereof, but is not limited thereto.

Illustrative compounds (1) 3- (methyloxycarbonylamino) salicylic acid (2) 3- (ethyloxycarbonylamino) salicylic acid (3) 3- (propyloxycarbonylamino) salicylic acid (4) 3- (isopropyloxycarbonyl) Amino) salicylic acid (5) 3- (butyloxycarbonylamino) salicylic acid (6) 3- (isobutyloxycarbonylamino) salicylic acid (7) 3- (sec-butyloxycarbonylamino)
Salicylic acid (8) 3- (t-butyloxycarbonylamino) salicylic acid (9) 3- (pentyloxycarbonylamino) salicylic acid (10) 3- (hexyloxycarbonylamino) salicylic acid (11) 3- (octyloxycarbonylamino) Salicylic acid (12) 3- (Nonyloxycarbonylamino) salicylic acid (13) 3- (Decyloxycarbonylamino) salicylic acid (14) 3- (Undecyloxycarbonylamino) salicylic acid (15) 3- (Dodecyloxycarbonylamino) salicylic acid (16) 3- (tridecyloxycarbonylamino) salicylic acid (17) 3- (tetradecyloxycarbonylamino)
Salicylic acid (18) 3- (pentadecyloxycarbonylamino)
Salicylic acid (19) 3- (Fluoromethyloxycarbonylamino) salicylic acid (20) 3- (Difluoromethyloxycarbonylamino) salicylic acid (21) 3- (Trifluoromethyloxycarbonylamino) salicylic acid (22) 3- (Chloromethyloxy) Carbonylamino)
Salicylic acid (23) 3- (Dichloromethyloxycarbonylamino) salicylic acid (24) 3- (Trichloromethyloxycarbonylamino) salicylic acid (25) 3- (Trifluoroethyloxycarbonylamino) salicylic acid (26) 3- (2-hydroxy Ethyloxycarbonylamino) salicylic acid (27) 3- (2-aminoethyloxycarbonylamino) salicylic acid (28) 3- (benzyloxycarbonylamino) salicylic acid (29) 3- (phenethyloxycarbonylamino) salicylic acid (30) 3- (Cyclopentyloxycarbonylamino) salicylic acid (31) 3- (cyclohexyloxycarbonylamino) salicylic acid (32) 3- (2-methylcyclohexyloxycarbonylamino) salicylic acid (33) 3- ( -Methylcyclohexyloxycarbonylamino) salicylic acid (34) 3- (4-methylcyclohexyloxycarbonylamino) salicylic acid (35) 3- (cycloheptyloxycarbonylamino) salicylic acid (36) 3- (cyclooctyloxycarbonylamino) salicylic acid ( 37) 3- (phenyloxycarbonylamino) salicylic acid (38) 3- (naphthyloxycarbonylamino) salicylic acid (39) 3- (2-chlorophenyloxycarbonylamino) salicylic acid (40) 3- (3-chlorophenyloxycarbonylamino) Salicylic acid (41) 3- (4-Chlorophenyloxycarbonylamino) salicylic acid (42) 3- (2-Fluorophenyloxycarbonylamino) salicylic acid (43) 3- (3-Fluorophthalic acid) Nyloxycarbonylamino) salicylic acid (44) 3- (4-fluorophenyloxycarbonylamino) salicylic acid (45) 3- (2-bromophenyloxycarbonylamino) salicylic acid (46) 3- (3-bromophenyloxycarbonylamino) Salicylic acid (47) 3- (4-Bromophenyloxycarbonylamino) salicylic acid (48) 4- (Methyloxycarbonylamino) salicylic acid (49) 4- (Ethyloxycarbonylamino) salicylic acid (50) 4- (Propyloxycarbonylamino) ) Salicylic acid (51) 4- (isopropyloxycarbonylamino)
Salicylic acid (52) 4- (butyloxycarbonylamino) salicylic acid (53) 4- (isobutyloxycarbonylamino) salicylic acid (54) 4- (sec-butyloxycarbonylamino) salicylic acid (55) 4- (t-butyloxycarbonyl) Amino) salicylic acid (56) 4- (pentyloxycarbonylamino) salicylic acid (57) 4- (hexyloxycarbonylamino) salicylic acid (58) 4- (octyloxycarbonylamino) salicylic acid (59) 4- (nonyloxycarbonylamino) Salicylic acid (60) 4- (decyloxycarbonylamino) salicylic acid (61) 4- (Undecyloxycarbonylamino) salicylic acid (62) 4- (Dodecyloxycarbonylamino) salicylic acid (63) 4- (Tridecylo) Shi carbonylamino) salicylate (64) 4- (tetradecyloxy carbonylamino)
Salicylic acid (65) 4- (pentadecyloxycarbonylamino)
Salicylic acid (66) 4- (Fluoromethyloxycarbonylamino) salicylic acid (67) 4- (Difluoromethyloxycarbonylamino) salicylic acid (68) 4- (Trifluoromethyloxycarbonylamino) salicylic acid (69) 4- (Chloromethyloxy) Carbonylamino)
Salicylic acid (70) 4- (Dichloromethyloxycarbonylamino) salicylic acid (71) 4- (Trichloromethyloxycarbonylamino) salicylic acid (72) 4- (Trifluoroethyloxycarbonylamino) salicylic acid (73) 4- (2-hydroxy Ethyloxycarbonylamino) salicylic acid (74) 4- (2-Aminoethyloxycarbonylamino) salicylic acid (75) 4- (Benzyloxycarbonylamino) salicylic acid (76) 4- (Phenethyloxycarbonylamino) salicylic acid (77) 4- (Cyclopentyloxycarbonylamino) salicylic acid (78) 4- (cyclohexyloxycarbonylamino) salicylic acid (78) 4- (2-methylcyclohexyloxycarbonylamino) salicylic acid (80) 4- ( -Methylcyclohexyloxycarbonylamino) salicylic acid (81) 4- (4-methylcyclohexyloxycarbonylamino) salicylic acid (82) 4- (cycloheptyloxycarbonylamino) salicylic acid (83) 4- (cyclooctyloxycarbonylamino) salicylic acid ( 84) 4- (phenyloxycarbonylamino) salicylic acid (85) 4- (naphthyloxycarbonylamino) salicylic acid (86) 4- (2-chlorophenyloxycarbonylamino) salicylic acid (87) 4- (3-chlorophenyloxycarbonylamino) Salicylic acid (88) 4- (4-Chlorophenyloxycarbonylamino) salicylic acid (89) 4- (2-Fluorophenyloxycarbonylamino) salicylic acid (90) 4- (3-Fluorophthalic acid) Nyloxycarbonylamino) salicylic acid (91) 4- (4-fluorophenyloxycarbonylamino) salicylic acid (92) 4- (2-bromophenyloxycarbonylamino) salicylic acid (93) 4- (3-bromophenyloxycarbonylamino) Salicylic acid: Calcium, barium, iron, aluminum, zinc, magnesium, and chromium salts of (94) 4- (4-bromophenyloxycarbonylamino) salicylic acid and the exemplified salicylic acid derivatives. Some of the metal salts of the exemplified compounds form hydrates, but even if they form hydrates, they can be applied to the present invention.

The compound represented by the general formula (1) is disclosed in
-72984. That is, the alkali metal salt of an aminosalicylic acid derivative has the general formula (2)

[0015]

Embedded image (Where R is the same as in the general formula (1)).

In the toner containing the charge control agent of the present invention, all colorants for color toners such as magenta, cyan, and yellow can be used as the colorant, as well as those for monochrome.

As the binder resin used in the present invention, all of those which have been used as binder resins for toner can be used. Specifically, polystyrene resins such as polystyrene, styrene-acrylic acid copolymer, styrene-methacrylic acid copolymer, styrene-acrylic acid ester copolymer, styrene-methacrylic acid ester copolymer, polyester resin, epoxy resin Phenolic resin, vinyl resin, polyolefin and the like.

In the toner containing the charge control agent of the present invention, a crosslinking agent can be used, and specific examples thereof include divinylbenzene, divinylnaphthalene, ethylene glycol diacrylate, ethylene glycol dimethacrylate, divinyl ether, divinyl sulfide and the like. It is possible.

In the toner containing the charge control agent of the present invention, specific examples of the magnetic material include metals such as iron, nickel and cobalt, and metals such as aluminum, copper, lead, magnesium, tin, bismuth, cadmium, and the like. manganese,
Examples thereof include alloys and mixtures with metals such as titanium, ferrite, magnetite, and iron oxides such as γ-iron oxide.

The toner containing the charge control agent of the present invention can be produced by any known method. Specifically, it is manufactured by kneading at a temperature higher than the melting point of the resin in a ball mill, cooling, pulverizing, and classifying.

After the preparation of the toner containing the charge control agent of the present invention, the flowability of the toner can be improved by adding silica, alumina, titania, or the like.

[0022]

EXAMPLES The present invention will be specifically described below with reference to examples. Production Example 1 (Production of Exemplified Compound 49) 4-Aminosalicylic acid sodium salt (dihydrate) 21
After 1.1 g (1.0 mol) was dissolved in 1 kg of methanol, 108.5 g (1.0 mol) of ethyl chloroformate was added dropwise at a temperature of 0 to 10 ° C. over 1.5 hours. After completion of the dropwise addition, stirring was further performed at a temperature of 0 to 10 ° C. for 1 hour. After adding 2 kg of water, the pH of the reaction mass is adjusted to 1 to 2 using hydrochloric acid, and the precipitated crystals are filtered, washed with water and dried at 60 ° C. to obtain the desired 4- (ethyloxycarbonylamino). 202.7 g of salicylic acid were obtained as white crystals. 90% yield.

Production Example 2 (Production of Exemplified Compound 50) The same operation as in Production Example 1 was carried out except that ethyl chloroformate was changed to propyl chloroformate, to obtain 227.3 g of 4- (propyloxycarbonylamino) salicylic acid.
Was obtained as white crystals. 95% yield.

Production Example 3 (Production of Exemplified Compound 52) The same operation as in Production Example 1 was carried out except that ethyl chloroformate was changed to butyl chloroformate, to give 240.6 g of 4- (butyloxycarbonylamino) salicylic acid. Obtained as white crystals. 95% yield.

Production Example 4 (Production of Exemplified Compound 58) The same operation as in Production Example 1 was carried out except that ethyl chloroformate was changed to octyl chloroformate, and 300.1 g of 4- (octyloxycarbonylamino) salicylic acid was obtained.
Was obtained as white crystals. 97% yield.

Production Example 5 (Production of calcium salt of Exemplified Compound 49) 4- (Ethyloxycarbonylamino) salicylic acid 1
6.5 g of 49% NaOH in 3.5 g (0.06 mol)
(0.08 mol) and 500 g of water to dissolve as sodium salt, and then 4.4 g of calcium chloride dihydrate
(0.03 mol) was added dropwise at room temperature over a period of 0.5 hour at room temperature. After dropping, the mixture was further stirred at room temperature for 1 hour. The reaction mass was neutralized with hydrochloric acid, and the precipitated crystals were filtered, washed with water and dried at 60 ° C. to obtain 13.2 g of the objective calcium salt of 4- (ethyloxycarbonylamino) salicylic acid as white crystals. Was. Yield 9
0%.

Production Example 6 (Production of calcium salt of Exemplified Compound 50) 4- (Ethyloxycarbonylamino) salicylic acid was added to 4
The same operation as in Production Example 5 was carried out except that-(propyloxycarbonylamino) salicylic acid was used, to obtain 13.8 g of calcium salt of 4- (propyloxycarbonylamino) salicylic acid as white crystals. 89% yield.

Production Example 7 (Production of calcium salt of Exemplified Compound 52) 4- (Ethyloxycarbonylamino) salicylic acid was converted to 4
The same operation as in Production Example 5 was performed except that-(butyloxycarbonylamino) salicylic acid was changed to calcium salt of 4- (butyloxycarbonylamino) salicylic acid.
0.0 g was obtained as white crystals. Yield 61%.

Production Example 8 (Production of calcium salt of Exemplified Compound 58) 4- (Ethyloxycarbonylamino) salicylic acid was converted to 4
The same operation as in Production Example 5 was carried out except for using-(octyloxycarbonylamino) salicylic acid, to obtain 16.2 g of calcium salt of 4- (octyloxycarbonylamino) salicylic acid as white crystals. 82% yield.

Production Example 9 (Production of barium salt of Exemplified Compound 49) 4- (Ethyloxycarbonylamino) salicylic acid 1
6.5 g of 49% NaOH in 3.5 g (0.06 mol)
(0.08 mol) and 500 g of water were added and dissolved as a sodium salt, followed by 7.3 g of barium chloride dihydrate.
(0.03 mol) was added dropwise at room temperature over a period of 0.5 hour at room temperature. After dropping, the mixture was further stirred at room temperature for 1 hour. The reaction mass is neutralized with hydrochloric acid, and the precipitated crystals are filtered, washed with water and dried at 60 ° C. to obtain 12.5 g of the objective barium salt of 4- (ethyloxycarbonylamino) salicylic acid as white crystals. Was. Yield 71
%.

Production Example 10 (Production of barium salt of Exemplified Compound 50) 4- (Ethyloxycarbonylamino) salicylic acid was converted to 4
The same operation as in Production Example 9 was performed, except that-(propyloxycarbonylamino) salicylic acid was changed to barium salt of 4- (propyloxycarbonylamino) salicylic acid.
2.9 g were obtained as white crystals. Yield 70%.

Production Example 11 (Production of barium salt of Exemplified Compound 52) 4- (Ethyloxycarbonylamino) salicylic acid was converted to 4
15. The same operation as in Production Example 9 was carried out except that-(butyloxycarbonylamino) salicylic acid was used, and the barium salt of 4- (butyloxycarbonylamino) salicylic acid was used.
0 g was obtained as white crystals. Yield 83%.

Production Example 12 (Production of barium salt of Exemplified Compound 58) 4- (Methyloxycarbonylamino) salicylic acid was converted to 4
The same operation as in Production Example 9 was performed, except that-(octyloxycarbonylamino) salicylic acid was changed to barium salt of 4- (octyloxycarbonylamino) salicylic acid.
2.4 g were obtained as white crystals. Yield 99%.

Production Example 13 (Production of zinc salt of Exemplified Compound 49) 4- (ethyloxycarbonylamino) salicylic acid 1
5.3 g of 49% NaOH in 3.5 g (0.06 mol)
(0.065 mol) and 500 g of water to dissolve as a sodium salt, and then 8.6 g of zinc sulfate heptahydrate
40 g of an aqueous solution containing (0.03 mol) was added dropwise at room temperature over 0.5 hours. After the dropwise addition, the mixture was further stirred at room temperature for 1 hour, and the precipitated crystals were filtered, washed with water, and dried at 60 ° C. to give 14.2 g of the objective zinc salt of 4- (ethyloxycarbonylamino) salicylic acid in white. Obtained as crystals. Yield 92%.

Production Example 14 (Production of zinc salt of Exemplified Compound 50) 4- (Ethyloxycarbonylamino) salicylic acid was converted to 4
The same operation as in Production Example 13 was carried out except that-(propyloxycarbonylamino) salicylic acid was changed to zinc salt of 4- (propyloxycarbonylamino) salicylic acid.
4.8 g were obtained as white crystals. Yield 91%.

Production Example 15 (Production of zinc salt of Exemplified Compound 52) 4- (ethyloxycarbonylamino) salicylic acid was converted to 4
The same operation as in Production Example 13 was carried out except that-(butyloxycarbonylamino) salicylic acid was changed to zinc salt of 4- (butyloxycarbonylamino) salicylic acid 16.2
g were obtained as white crystals. 95% yield.

Production Example 16 (Production of zinc salt of Exemplified Compound 58) 4- (Ethyloxycarbonylamino) salicylic acid was converted to 4
The same operation as in Production Example 13 was carried out except that-(octyloxycarbonylamino) salicylic acid was used, to obtain 19.6 g of zinc salt of 4- (octyloxycarbonylamino) salicylic acid monohydrate as white crystals. 95%).
When 10.0 g of the obtained zinc salt of 4- (octyloxycarbonylamino) salicylic acid was treated at 110 ° C. for 6 hours, the zinc salt of 4- (octyloxycarbonylamino) salicylic acid from which the hydrate was removed was 9 g. 0.7 g was obtained.

Production Example 17 (Production of Aluminum Salt of Exemplified Compound 49) 4- (Ethyloxycarbonylamino) salicylic acid 1
5.3 g of 49% NaOH in 3.5 g (0.06 mol)
(0.065 mol) and water (500 g), and dissolved as a sodium salt.
40 g of an aqueous solution containing 5 g (0.02 mol) was added at room temperature to 0.1 g.
It was charged dropwise over 5 hours. After the dropwise addition, the mixture was further stirred at room temperature for 1 hour, and the precipitated crystals were filtered, washed with water and washed with water.
13.4 g of the desired aluminum salt of 4- (ethyloxycarbonylamino) salicylic acid by drying at
Was obtained as white crystals. 96% yield.

Production Example 18 (Production of Aluminum Salt of Exemplary Compound 50) 4- (Ethyloxycarbonylamino) salicylic acid was converted to 4
The same operation as in Production Example 17 was carried out except for using-(propyloxycarbonylamino) salicylic acid, to obtain 13.9 g of aluminum salt of 4- (propyloxycarbonylamino) salicylic acid as white crystals. 94% yield.

Production Example 19 (Production of Aluminum Salt of Exemplified Compound 52) 4- (Ethyloxycarbonylamino) salicylic acid was converted to 4
The same operation as in Production Example 17 was carried out except for using-(butyloxycarbonylamino) salicylic acid, to obtain 15.2 g of aluminum salt of 4- (butyloxycarbonylamino) salicylic acid as white crystals. 97% yield.

Production Example 20 (Production of Aluminum Salt of Exemplified Compound 58) 4- (Ethyloxycarbonylamino) salicylic acid was converted to 4
The same operation as in Production Example 17 was carried out except for using-(octyloxycarbonylamino) salicylic acid, to obtain 18.2 g of aluminum salt of 4- (octyloxycarbonylamino) salicylic acid as white crystals. 96% yield.

Examples 1 to 24 (Evaluation as Charge Control Agent) Compounds (1 part by weight) obtained in Production Examples 1 to 20 at 22 ° C./55% and 35 ° C./85%, respectively, and a carrier Non-coated iron powder F-100 (99 parts by weight) was mixed for 5 minutes with a paint conditioner, and the charge amount was measured by a blow-off method. Table 1 shows the results.

[0043]

[Table 1]

Comparative Examples 1 to 3 A metal charge of 3,5-di-t-butylsalicylic acid (hereinafter referred to as DBSA), which is an existing charge control agent, was treated in the same manner, and the charge amount was measured. Table 2 shows the results.

[0045]

[Table 2]

[0046]

According to the present invention, a charge control agent for a toner for electrostatic charge development having a stable charge performance even at high temperature and high humidity can be provided.

Claims (3)

[Claims] 1. A compound of the general formula (1) (Wherein, R represents an alkyl group which may have a substituent, an aryl group which may have a substituent, or an aralkyl group which may have a substituent, and R ′ is a hydrogen atom, an alkyl group, X1 and X2 represent a hydrogen atom, an alkyl group optionally having a substituent, an aryl group optionally having a substituent, an alkoxy group optionally having a substituent, a substituent Represents an aralkyl group or a halogen atom, which may have, M represents a hydrogen ion or a metal ion, n represents an integer of 1 to 3 corresponding to the valence of M, and x
Represents a charge control agent for a toner for electrostatic charge development using a compound represented by the following formula: 2. The charge controlling agent according to claim 1, wherein X1 and X2 are hydrogen atoms, and R 'is a hydrogen atom. 3. The charge control agent according to claim 1, wherein M is a hydrogen ion, a zinc ion, an aluminum ion, a calcium ion, a barium ion or an iron ion.