Toner for developing electrostatic images

Abstract

Relates to an electrostatic charge image developing toner excellent in weather resistance and image density. 【Solution means】An electrostatic charge image developing toner containing a crystalline polyester resin, an amorphous polyester resin, a quinacridone pigment, and a hydroxy group-containing amide compound, wherein the content of the quinacridone pigment is 4 parts by mass or more and 12 parts by mass or less with respect to 100 parts by mass of the total amount of the crystalline polyester resin and the amorphous polyester resin, and the hydroxy group-containing amide compound is represented by the formula (I): R 1 -CONH-X-NHCO-R 2 (I) Or the formula (II): R 3 -CONH-R 4 (II) And is a compound represented by the formula, and the content of the hydroxy group-containing amide compound is 0.4 parts by mass or more and 13 parts by mass or less with respect to 100 parts by mass of the total amount of the crystalline polyester resin and the amorphous polyester resin.

Description

Technical Field

[0001] The present invention relates to an electrostatic charge image developing toner used for developing a latent image formed in an electrophotographic method, an electrostatic recording method, an electrostatic printing method, or the like.

Background Art

[0002] From the viewpoints of storage stability, durability, chargeability, etc., it has been studied to use an amide compound as a toner raw material together with a crystalline polyester resin and an amorphous polyester resin (see Patent Documents 1 to 4).

[0003] In recent years, printing using toner has come to be used in industrial printing and commercial printing. In such printing, since printed matter is often used outdoors, weather resistance of the printed matter is required. In addition, there are many applications for high-quality images such as photographs, and it is required to improve image density.

Prior Art Documents

Patent Documents

[0004]

Patent Document 1

Patent Document 2

Patent Document 3

Patent Document 4

Summary of the Invention

Problems to be Solved by the Invention

[0005] Among the magenta pigments used in electrostatic developer toners, quinacridone pigments are known for their high weather resistance. Quinacridone pigments have high weather resistance due to strong intermolecular hydrogen bonds and layered molecular structure. However, these same intermolecular hydrogen bonds result in poor dispersibility in polyester resins, leading to low coloring power and the inability to obtain printed materials with high image density.

[0006] This invention relates to a toner for electrostatic image development that exhibits excellent weather resistance and image density. [Means for solving the problem]

[0007] The present invention relates to a toner for developing electrostatic images, comprising a crystalline polyester resin, an amorphous polyester resin, a quinacridone pigment, and a hydroxyl group-containing amide compound, wherein the content of the quinacridone pigment is 4 parts by mass or more and 12 parts by mass or less per 100 parts by mass of the total amount of the crystalline polyester resin and the amorphous polyester resin, and the hydroxyl group-containing amide compound is of formula (I): R 1 -CONH-X-NHCO-R 2 (I) (In the formula, R 1 and R 2 Each of these is independently a hydroxyalkyl group having 12 to 22 carbon atoms, and X is a divalent hydrocarbon group having 2 to 12 carbon atoms. Or formula (II): R 3 -CONH-R 4 (II) (In the formula, R 3 R is a hydroxyalkyl group having 12 to 22 carbon atoms. 4 (This is a hydroxyalkyl group having 2 to 22 carbon atoms.) The present invention relates to a toner for developing electrostatic images, wherein the compound is represented by [formula], and the content of the hydroxyl group-containing amide compound is 0.4 parts by mass or more and 13 parts by mass or less, based on 100 parts by mass of the total amount of the crystalline polyester resin and the amorphous polyester resin. [Effects of the Invention]

[0008] The electrostatic image developing toner of the present invention exhibits excellent effects in terms of weather resistance and image density. [Modes for carrying out the invention]

[0009] The electrostatic image developing toner of the present invention contains a crystalline polyester resin, an amorphous polyester resin, a quinacridone pigment, and an amide compound, and is characterized in that it contains a predetermined hydroxyl group-containing amide compound as the amide compound. The reason why the effects of the present invention are achieved is not clear, but it is presumed to be as follows. Note that the following mechanism is a hypothesis and is not limited thereto.

[0010] In this invention, by using a fatty acid amide compound containing a hydroxyl group (hydroxyl group-containing amide compound), the NH and OH groups of the hydroxy fatty acid amide compound form strong hydrogen bonds with the NH group of the quinacridone pigment. The hydroxy fatty acid amide compound acts as an adsorption group to the pigment, improving pigment dispersibility and increasing the image density of printed materials. Furthermore, it is believed that the interaction between the hydroxy fatty acid amide compound and the quinacridone pigment stabilizes the quinacridone pigment in the toner, further improving weather resistance.

[0011] Examples of crystalline polyester resins include crystalline polyester resins, composite resins containing crystalline polyester resins and vinyl resins such as styrene-acrylic resins, epoxy resins, polycarbonate, polyurethane, and other resins. Among these, crystalline polyester resins are preferred.

[0012] The crystalline or amorphous nature of a resin is determined by its crystallinity index. The crystallinity index is defined as the ratio of the resin's softening point to its maximum endothermic peak temperature (softening point (°C) / maximum endothermic peak temperature (°C)) in the measurement method described in the examples below. A crystalline resin is one in which the crystallinity index is between 0.6 and 1.4. An amorphous resin is one in which no endothermic peak is observed, or if observed, the crystallinity index is less than 0.6 or greater than 1.4. The crystallinity of a resin can be adjusted by the type and ratio of raw material monomers, as well as the manufacturing conditions (e.g., reaction temperature, reaction time, cooling rate). The maximum endothermic peak temperature refers to the temperature of the peak with the largest peak area among the observed endothermic peaks. In crystalline resins, the maximum endothermic peak temperature is defined as the melting point.

[0013] As for the crystalline polyester resin, a polycondensate of an alcohol component containing an aliphatic diol and a carboxylic acid component is preferred.

[0014] Examples of aliphatic diols include ethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, 1,4-butenediol, 1,7-heptanediol, 1,8-octanediol, neopentyl glycol, 1,9-nonanediol, 1,10-decanediol, 1,11-undecanediol, and 1,12-dodecanediol.

[0015] The aliphatic diol has two or more carbon atoms, and from the viewpoint of low-temperature fixability, it is preferably 12 or less, more preferably 6 or less, and even more preferably 4 or less.

[0016] From the viewpoint of improving the low-temperature fixability of the toner, aliphatic diols are preferably those having a hydroxyl group at the end of the carbon chain, and more preferably α,ω-linear alkanediols.

[0017] As the aliphatic diol, an aliphatic diol having 2 to 6 carbon atoms is preferred, and ethylene glycol is more preferred.

[0018] The aliphatic diol content is preferably 80 mol% or more, more preferably 90 mol% or more, even more preferably 95 mol% or more, and 100 mol% or less, in the alcohol component.

[0019] Examples of alcohol components other than aliphatic diols include alkylene oxide adducts of bisphenol A, aromatic diols such as bisphenol A, hydrogenated bisphenol A, sorbitol, pentaerythritol, glycerin, trivalent or higher alcohols such as trimethylolpropane, etc.

[0020] The carboxylic acid component preferably contains an aliphatic dicarboxylic acid compound.

[0021] Examples of aliphatic dicarboxylic acid compounds include succinic acid (4 carbon atoms), fumaric acid (4 carbon atoms), adipic acid (6 carbon atoms), suberic acid (8 carbon atoms), azelaic acid (9 carbon atoms), sebacic acid (10 carbon atoms), dodecanediic acid (12 carbon atoms), tetradecanediic acid (14 carbon atoms), anhydrides of these acids, and alkyl esters of these acids with 1 to 3 carbon atoms.

[0022] From the viewpoint of heat-resistant storage, the carbon number of the aliphatic dicarboxylic acid compound is preferably 10 or more, more preferably 12 or more, and from the viewpoint of low-temperature fixability, it is preferably 16 or less, more preferably 14 or less. Here, the carbon number of the alkyl group when the aliphatic dicarboxylic acid compound is an alkyl ester is not included in the above carbon number.

[0023] The content of aliphatic dicarboxylic acid compounds in the carboxylic acid component is preferably 50 mol% or more, more preferably 60 mol% or more, even more preferably 70 mol% or more, even more preferably 80 mol% or more, and 100 mol% or less, from the viewpoint of hydrophobicity. If the carboxylic acid component includes aliphatic monocarboxylic acid compounds, the content is preferably 98 mol% or less, more preferably 97 mol% or less.

[0024] From the viewpoint of electrostatic stability, it is preferable that the carboxylic acid component further contains an aliphatic monocarboxylic acid compound.

[0025] Examples of aliphatic monocarboxylic acid compounds include capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid, and alkyl esters of these acids in which the alkyl group has 1 to 3 carbon atoms.

[0026] From the viewpoint of glossiness, the carbon number of the aliphatic monocarboxylic acid compound is preferably 12 or more, more preferably 18 or more, and even more preferably 20 or more. From the viewpoint of low-temperature fixability, it is preferably 30 or less, more preferably 24 or less, and even more preferably 22 or less. Here, the carbon number of the alkyl group when the aliphatic monocarboxylic acid compound is an alkyl ester is not included in the above carbon number.

[0027] When the carboxylic acid component contains an aliphatic monocarboxylic acid compound, the content of the aliphatic monocarboxylic acid compound is preferably 2 mol% or more, more preferably 3 mol% or more, and preferably 15 mol% or less, and more preferably 10 mol% or less, in the carboxylic acid component.

[0028] Other carboxylic acid components include aromatic dicarboxylic acid compounds such as phthalic acid, isophthalic acid, and terephthalic acid, and trivalent or higher carboxylic acid compounds such as trimellitic acid and pyromellitic acid.

[0029] In this specification, macromonomers and hydroxycarboxylic acids are not included in the alcohol and carboxylic acid components.

[0030] The equivalent ratio of the carboxyl group of the carboxylic acid component to the hydroxyl group of the alcohol component (COOH group / OH group) is preferably 0.7 or higher, more preferably 0.8 or higher, from the viewpoint of electrostatic stability, and preferably 1.3 or lower, more preferably 1.2 or lower, from the viewpoint of low-temperature fixability.

[0031] Crystalline polyester resins can be produced, for example, by polycondensing an alcohol component and a carboxylic acid component in an inert gas atmosphere, preferably in the presence of an esterification catalyst, and optionally in the presence of a co-catalyst, polymerization inhibitor, etc., at a temperature preferably 120°C or higher, more preferably 180°C or higher, and preferably 230°C or lower, more preferably 220°C or lower.

[0032] Examples of esterification catalysts include tin compounds such as dibutyltin oxide and tin(II) 2-ethylhexanoate, and titanium compounds such as titanium diisopropoxybis(triethanolamine) and titanium dihydroxybis(triethanolamine). The amount of esterification catalyst used is preferably 0.01 parts by mass or more, more preferably 0.1 parts by mass or more, and preferably 1.5 parts by mass or less, and more preferably 1 part by mass or less, per 100 parts by mass of the total amount of alcohol and carboxylic acid components. Examples of co-catalysts for the esterification catalyst include gallic acid. The amount of co-catalyst used is preferably 0.001 parts by mass or more, more preferably 0.01 parts by mass or more, and preferably 0.5 parts by mass or less, and more preferably 0.1 parts by mass or less, per 100 parts by mass of the total amount of alcohol and carboxylic acid components. Examples of polymerization inhibitors include tert-butylcatechol. The amount of polymerization inhibitor used is preferably 0.001 parts by mass or more, more preferably 0.01 parts by mass or more, and preferably 0.5 parts by mass or less, and more preferably 0.1 parts by mass or less, based on 100 parts by mass of the total amount of alcohol and carboxylic acid components.

[0033] In this invention, the polyester resin may be a polyester resin that has been modified to such an extent that its properties are not substantially impaired. Examples of modified polyester resins include polyester resins that have been grafted or blocked with phenol, urethane, epoxy, etc., by methods described in Japanese Patent Publication No. 11-133668, Japanese Patent Publication No. 10-239903, Japanese Patent Publication No. 8-20636, etc. Among modified polyester resins, urethane-modified polyester resins obtained by urethane elongation of polyester resin with a polyisocyanate compound are preferred.

[0034] The softening point of the crystalline polyester resin is preferably 50°C or higher, more preferably 65°C or higher, and even more preferably 70°C or higher, from the viewpoint of hot offset resistance, and preferably 120°C or lower, more preferably 110°C or lower, from the viewpoint of low-temperature fixation.

[0035] The melting point of the crystalline polyester resin is preferably 45°C or higher, more preferably 60°C or higher, and even more preferably 65°C or higher, from the viewpoint of heat-resistant storage, and preferably 115°C or lower, more preferably 105°C or lower, from the viewpoint of low-temperature fixation.

[0036] The ratio of the softening point to the melting point (softening point / melting point) of the crystalline polyester resin is preferably 0.7 or higher, more preferably 0.9 or higher, and preferably 1.3 or lower, more preferably 1.2 or lower.

[0037] The weight-average molecular weight of the crystalline polyester resin is preferably 10,000 or more, more preferably 15,000 or more, from the viewpoint of heat-resistant storage, and preferably 30,000 or less, more preferably 25,000 or less, from the viewpoint of low-temperature fixation.

[0038] From the viewpoint of low-temperature fixing property, the content of the crystalline polyester resin in the total amount of the crystalline polyester resin and the amorphous polyester resin is preferably 5% by mass or more, more preferably 8% by mass or more, still more preferably 10% by mass or more, and preferably 25% by mass or less, more preferably 20% by mass or less, still more preferably 17% by mass or less.

[0039] Examples of the amorphous polyester resin include an amorphous polyester resin, a composite resin containing an amorphous polyester resin and a vinyl resin such as a styrene-acrylic resin, a resin such as an epoxy resin, a polycarbonate, and a polyurethane. Among these, an amorphous polyester resin is preferable.

[0040] As the amorphous polyester resin, an amorphous polyester resin which is a polycondensate of an alcohol component containing an alkylene oxide adduct of bisphenol A and a carboxylic acid component is preferable.

[0041] As the alkylene oxide adduct of bisphenol A, the formula (III):

[0042] [Chemical formula]

[0043] (In the formula, OR 5 and R 5 O is an oxyalkylene group, R 5 is an ethylene group and / or a propylene group, x and y represent the average number of moles of alkylene oxide added, and are each a positive number. The value of the sum of x and y is 1 or more, preferably 1.5 or more, and 16 or less, preferably 8 or less, more preferably 6 or less, still more preferably 4 or less) The compound represented by is preferable, and examples include an ethylene oxide adduct of bisphenol A and a propylene oxide adduct of bisphenol A.

[0044] From the viewpoint of low-temperature fixability, the content of the bisphenol A alkylene oxide adduct is preferably 40 mol% or more, more preferably 60 mol% or more, even more preferably 80 mol% or more, even more preferably 90 mol% or more, and even more preferably 95 mol% or more, and 100 mol% or less, in the alcohol component.

[0045] Other alcohol components include aliphatic diols such as ethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,4-butanediol, 2,3-butanediol, 1,5-pentanediol, 1,6-hexanediol, and neopentyl glycol, as well as trivalent or higher alcohols such as bisphenol A, hydrogenated bisphenol A, sorbitol, pentaerythritol, glycerin, and trimethylolpropane.

[0046] Examples of carboxylic acid components include aromatic dicarboxylic acid compounds, aliphatic dicarboxylic acid compounds, and trivalent or higher carboxylic acid compounds.

[0047] Examples of aromatic dicarboxylic acid compounds include phthalic acid, isophthalic acid, terephthalic acid, anhydrides of these acids, and alkyl esters of these acids with 1 to 3 carbon atoms.

[0048] The content of aromatic dicarboxylic acid compounds is preferably 40 mol% or more, more preferably 60 mol% or more, even more preferably 70 mol% or more, and preferably 95 mol% or less, and more preferably 90 mol% or less, from the viewpoint of heat resistance and storage properties among the carboxylic acid components.

[0049] Examples of aliphatic dicarboxylic acid compounds include fumaric acid, maleic acid, succinic acid, succinic acid derivatives substituted with hydrocarbon groups, glutaric acid, adipic acid, sebacic acid, anhydrides of these acids, and alkyl esters of these acids with 1 to 3 carbon atoms.

[0050] Examples of carboxylic acid compounds with a valency of 3 or higher include trimellitic acid, pyromellitic acid, anhydrides of these acids, and alkyl esters of these acids with 1 to 3 carbon atoms.

[0051] The alcohol component may contain a monohydric alcohol, and the carboxylic acid component may contain a monohydric carboxylic acid compound, as appropriate.

[0052] The equivalent ratio (COOH group / OH group) of the carboxyl group of the carboxylic acid component to the hydroxyl group of the alcohol component is preferably 0.6 or higher, more preferably 0.7 or higher, even more preferably 0.8 or higher, and preferably 1.3 or lower, more preferably 1.2 or lower, from the viewpoint of adjusting the softening point of the polyester resin.

[0053] The polycondensation reaction conditions between the alcohol component and the carboxylic acid component of the amorphous polyester resin are the same as those for the crystalline polyester resin, except that the preferred reaction temperature is 160°C or higher, more preferably 200°C or higher, and 250°C or lower, more preferably 240°C or lower.

[0054] The softening point of amorphous polyester resin is preferably 70°C or higher, more preferably 85°C or higher, and even more preferably 100°C or higher, from the viewpoint of electrostatic stability, and preferably 170°C or lower, more preferably 160°C or lower, and even more preferably 150°C or lower, from the viewpoint of low-temperature fixability.

[0055] From the viewpoint of low-temperature fixability and fixation width, the amorphous polyester resin is preferably composed of amorphous polyester resins with different softening points. The difference in softening points between the two amorphous polyester resins is preferably 10°C or more, more preferably 15°C or more, and preferably 60°C or less, more preferably 50°C or less.

[0056] The softening point of the amorphous polyester resin (resin AH) with a high softening point is preferably 100°C or higher, more preferably 110°C or higher, from the viewpoint of fixing width, and preferably 170°C or lower, more preferably 160°C or lower, and even more preferably 150°C or lower, from the viewpoint of low-temperature fixing properties.

[0057] The weight-average molecular weight of resin AH is preferably 50,000 or more, more preferably 100,000 or more, and preferably 200,000 or less, more preferably 150,000 or less.

[0058] Furthermore, the softening point of the amorphous polyester resin (resin AL) with a lower softening point is preferably 70°C or higher, more preferably 85°C or higher, from the viewpoint of electrostatic stability, and preferably 120°C or lower, more preferably 110°C or lower, and even more preferably 100°C or lower, from the viewpoint of low-temperature fixation.

[0059] The weight-average molecular weight of resin AL is preferably 3,000 or more, more preferably 4,000 or more, and preferably 9,000 or less, more preferably 8,000 or less.

[0060] The mass ratio of resin AL to resin AH (resin AL / resin AH) is preferably 55 / 45 or more, more preferably 60 / 40 or more, even more preferably 65 / 35 or more, and preferably 90 / 10 or less, more preferably 85 / 15 or less, and even more preferably 80 / 20 or less.

[0061] The glass transition temperature of amorphous polyester resin is preferably 40°C or higher, more preferably 45°C or higher, from the viewpoint of storage properties, and preferably 80°C or lower, more preferably 70°C or lower, from the viewpoint of electrostatic stability.

[0062] The content of amorphous polyester resin is preferably 70% by mass or more, more preferably 80% by mass or more, even more preferably 90% by mass or more, even more preferably 95% by mass or more, and 100% by mass or less, in the amorphous polyester resin.

[0063] Furthermore, the content of amorphous polyester resin in the total amount of amorphous polyester resin and crystalline polyester resin is preferably 75% by mass or more, more preferably 80% by mass or more, even more preferably 83% by mass or more, and preferably 95% by mass or less, more preferably 92% by mass or less, and even more preferably 90% by mass or less.

[0064] The mass ratio of crystalline polyester resin to amorphous polyester resin (crystalline polyester resin / amorphous polyester resin) is preferably 5 / 95 or more, more preferably 8 / 92 or more, even more preferably 10 / 90 or more, and preferably 25 / 75 or less, more preferably 20 / 80 or less, and even more preferably 17 / 83 or less.

[0065] In the toner of the present invention, crystalline polyester resin and amorphous polyester resin are contained as binder resins (binders).

[0066] The total content of crystalline polyester resin and amorphous polyester resin in the binder resin is preferably 70% by mass or more, more preferably 80% by mass or more, even more preferably 90% by mass or more, even more preferably 95% by mass or more, and 100% by mass or less.

[0067] Other binder resins include vinyl resins such as styrene-acrylic resin, polyamide resin, epoxy resin, polycarbonate resin, polyurethane resin, and composite resins containing two or more of these resins.

[0068] The binder resin content in the toner is preferably 60% by mass or more, more preferably 70% by mass or more, even more preferably 75% by mass or more, and preferably 97% by mass or less, more preferably 95% by mass or less, and even more preferably 93% by mass or less.

[0069] From the viewpoint of improving image density, the quinacridone-based pigment preferably contains at least one selected from the group consisting of dimethylquinacridone pigment, unsubstituted quinacridone pigment, and dichloroquinacridone pigment, and more preferably contains dimethylquinacridone pigment.

[0070] CI Pigment Red 122 is preferred as the dimethylquinacridone pigment.

[0071] Examples of unsubstituted quinacridone pigments include CI Pigment Violet 19, CI Pigment Red 206, CI Pigment Orange 48, and 49.

[0072] Examples of dichloroquinacridone pigments include CI Pigment Red 202 and 209.

[0073] The quinacridone pigment content is 4 parts by mass or more, preferably 5 parts by mass or more, more preferably 6 parts by mass or more, based on 100 parts by mass of the total amount of crystalline polyester resin and amorphous polyester resin. From the viewpoint of low-temperature fixability, it is 12 parts by mass or less, preferably 11 parts by mass or less, more preferably 10 parts by mass or less.

[0074] The toner of the present invention may contain colorants other than the quinacridone pigment, as long as the effects of the present invention are not impaired. However, the content of the quinacridone pigment is preferably 80% by mass or more, more preferably 90% by mass or more, even more preferably 95% by mass or more, and 100% by mass or less, in the colorants. Other colorants include carbon black, phthalocyanine blue, permanent brown FG, brilliant first scarlet, pigment green B, rhodamine-B base, solvent red 49, solvent red 146, solvent blue 35, carmine 6B, disazo yellow, and the like.

[0075] Hydroxyl group-containing amide compounds are given by formula (I): R 1 -CONH-X-NHCO-R2 (I) (In the formula, R 1 and R 2 Each of these is independently a hydroxyalkyl group having 12 to 22 carbon atoms, and X is a divalent hydrocarbon group having 2 to 12 carbon atoms. Or formula (II): R 3 -CONH-R 4 (II) (In the formula, R 3 R is a hydroxyalkyl group having 12 to 22 carbon atoms. 4 (This is a hydroxyalkyl group having 2 to 22 carbon atoms.) The compound is represented by [formula]. The toner of the present invention may contain either the compound represented by formula (I) or the compound represented by formula (II) as a hydroxyl group-containing amide compound, or it may contain both the compound represented by formula (I) and the compound represented by formula (II).

[0076] R 1 , R 2 and R 3 The number of carbon atoms in the hydroxyalkyl group is preferably 13 or more, more preferably 15 or more, and preferably 21 or less, more preferably 19 or less, from the viewpoint of further improving the weather resistance and image density of the printed material.

[0077] R 4 The number of carbon atoms in the hydroxyalkyl group is preferably 10 or less, more preferably 6 or less, from the viewpoint of further improving the weather resistance and image density of the printed material.

[0078] R 1 ~R 4 The alkyl group in this combination may be branched or linear, but it is preferably linear.

[0079] Examples of divalent hydrocarbon groups in X include divalent aliphatic hydrocarbon groups and divalent aromatic hydrocarbon groups.

[0080] Examples of divalent aliphatic hydrocarbon groups include ethylene, trimethylene, tetramethylene, and hexamethylene groups.

[0081] Examples of divalent aromatic hydrocarbon groups include phenylene groups, m-xylylene groups, and p-xylylene groups.

[0082] The number of carbon atoms in the divalent hydrocarbon group of X is preferably 10 or less, more preferably 8 or less, and even more preferably 6 or less.

[0083] Specific examples of hydroxyl group-containing amide compounds represented by formula (I) include 12-hydroxystearate ethylenebisamide, 12-hydroxystearate hexamethylenebisamide, 12-hydroxystearate xylylenebisamide, and 12-hydroxypalmitate ethylenebisamide.

[0084] Specific examples of hydroxyl group-containing amide compounds represented by formula (II) include hydroxyethyl 12-hydroxystearate and hydroxyethyl 12-hydroxypalmitate.

[0085] The melting point of the hydroxyl group-containing amide compound is preferably 100°C or higher, more preferably 110°C or higher, and even more preferably 120°C or higher, from the viewpoint of glossiness, and preferably 180°C or lower, more preferably 170°C or lower, and even more preferably 160°C or lower, from the viewpoint of low-temperature fixability.

[0086] The content of the hydroxyl group-containing amide compound is 0.4 parts by mass or more, preferably 0.5 parts by mass or more, more preferably 0.6 parts by mass or more, even more preferably 0.7 parts by mass or more, even more preferably 0.8 parts by mass or more, and 13 parts by mass or less, preferably 12 parts by mass or less, more preferably 7 parts by mass or less, even more preferably 4 parts by mass or less, and even more preferably 2 parts by mass or less, based on 100 parts by mass of the total amount of crystalline polyester resin and amorphous polyester resin.

[0087] Furthermore, the mass ratio of the hydroxyl group-containing amide compound to the quinacridone pigment (hydroxyl group-containing amide compound / quinacridone pigment) is preferably 5 / 95 or more, more preferably 10 / 90 or more, even more preferably 13 / 87 or more, and preferably 70 / 30 or less, more preferably 50 / 50 or less, even more preferably 30 / 70 or less, and even more preferably 20 / 80 or less.

[0088] The toner of the present invention may further contain additives such as release agents, charge control agents, magnetic powders, flowability enhancers, conductivity modifiers, reinforcing fillers such as fibrous materials, antioxidants, and cleaning properties enhancers.

[0089] Examples of mold release agents include hydrocarbon waxes and their oxides, such as polypropylene wax, polyethylene wax, ethylene propylene copolymer wax, microcrystalline wax, paraffin wax, and Fischer-Tropsch wax; ester waxes such as carnauba wax, montane wax and their deoxidizing waxes, and fatty acid ester waxes; and fatty acid amides, fatty acids, higher alcohols, fatty acid metal salts, etc., which can be used individually or in combination of two or more.

[0090] The melting point of the release agent is preferably 60°C or higher, more preferably 70°C or higher, from the viewpoint of toner transferability, and preferably 160°C or lower, more preferably 140°C or lower, even more preferably 120°C or lower, and even more preferably 110°C or lower, from the viewpoint of low-temperature fixation.

[0091] The release agent content is preferably 0.5 parts by mass or more, more preferably 1 part by mass or more, even more preferably 1.5 parts by mass or more, and preferably 10 parts by mass or less, more preferably 8 parts by mass or less, and even more preferably 7 parts by mass or less, per 100 parts by mass of binder resin, from the viewpoint of low-temperature fixation and offset resistance of the toner and dispersibility in the binder resin.

[0092] The charge control agent is not particularly limited and may contain either a positively charged charge control agent or a negatively charged charge control agent.

[0093] Positively charged charge control agents include nigrosine dyes, such as "Nigrosine Base EX," "Oil Black BS," "Oil Black SO," "Bontron N-01," "Bontron N-04," "Bontron N-07," "Bontron N-09," "Bontron N-11," and "Bontron N-79" (all manufactured by Orient Chemical Industries, Ltd.); triphenylmethane-based dyes containing tertiary amines as side chains; quaternary ammonium salt compounds, such as "Bontron P-51" (manufactured by Orient Chemical Industries, Ltd.), cetyltrimethylammonium bromide, and "COPY CHARGE PX." Examples include VP435 (manufactured by Clariant), polyamine resins such as AFP-B (manufactured by Orient Chemical Industries, Ltd.), imidazole derivatives such as PLZ-2001 and PLZ-8001 (both manufactured by Shikoku Chemicals, Ltd.), and styrene-acrylic resins such as FCA-701PT and FCA-201-PS (manufactured by Fujikura Chemicals, Ltd.).

[0094] Furthermore, as negative charge control agents, metal-containing azo dyes, such as "Barifast Black 3804," "Bontron S-31," "Bontron S-32," "Bontron S-34," and "Bontron S-36" (all manufactured by Orient Chemical Industries, Ltd.), "Eisenspiron Black TRH," and "T-77" (manufactured by Hodogaya Chemical Co., Ltd.); metal compounds of benzyl acid compounds, such as "LR-147" and "LR-297" (both manufactured by Nippon Carlit Co., Ltd.); metal compounds of salicylic acid compounds, such as "Bontron E-81," "Bontron E-84," "Bontron E-88," and "Bontron E-304" (all manufactured by Orient Chemical Industries, Ltd.), and "TN-105" (manufactured by Hodogaya Chemical Co., Ltd.); copper phthalocyanine dyes; and quaternary ammonium salts, such as "COPY CHARGE NX" Examples include VP434 (manufactured by Clariant), nitroimidazole derivatives, organometallic compounds, etc.

[0095] From the viewpoint of the charge stability of the toner, the content of the charge control agent is preferably 0.01 parts by mass or more, more preferably 0.2 parts by mass or more, and preferably 10 parts by mass or less, more preferably 5 parts by mass or less, even more preferably 3 parts by mass or less, and even more preferably 2 parts by mass or less, per 100 parts by mass of the binder resin.

[0096] The toner of the present invention may be obtained by any of the conventionally known methods, such as the melt-kneading method, the emulsification-coagulation method, or the suspension polymerization method, and may also be a toner having a core-shell structure. However, from the viewpoint of the mixability of the toner raw materials, pulverized toner is preferred, and pulverized toner obtained by the melt-kneading method, that is, pulverized toner obtained by a method including the steps of melt-kneading the raw materials and pulverizing the resulting mixture, is more preferred. Specifically, for example, a crystalline polyester resin, an amorphous polyester resin, a quinacridone pigment, and a hydroxyl group-containing amide compound, along with raw materials such as a mold release agent and a charge control agent as needed, can be uniformly mixed in a mixer such as a Henschel mixer, then melt-kneaded in a closed-type kneader, a single-screw or twin-screw extruder, an open-roll type kneader, etc., and then cooled, pulverized, and classified to produce the toner. Furthermore, from the viewpoint of dispersibility of the hydroxyl group-containing amide compound, it is preferable to use the hydroxyl group-containing amide compound after mixing all or part of the amorphous polyester resin with it at a temperature above the melting point of the hydroxyl group-containing amide compound. It is even more preferable to add and mix the hydroxyl group-containing amide compound after the polycondensation reaction of the raw material monomers of the amorphous polyester resin at a temperature above the melting point of the hydroxyl group-containing amide compound.

[0097] In order to improve the transferability of the toner of the present invention, it is preferable to use external additives. Examples of external additives include inorganic fine particles such as silica, alumina, titania, zirconia, tin oxide, and zinc oxide, and organic fine particles such as melamine resin fine particles and polytetrafluoroethylene resin fine particles, and two or more may be used in combination. Among these, silica is preferred, and from the viewpoint of the transferability of the toner, hydrophobic silica that has been treated to hydrophobicity is more preferable.

[0098] Examples of hydrophobic agents used to hydrophobize the surface of silica particles include hexamethyldisilazane (HMDS), dimethyldichlorosilane (DMDS), cyclic silazane, silicone oil, aminosilane, octyltriethoxysilane (OTES), and methyltriethoxysilane.

[0099] The average particle size of the external additive is preferably 5 nm or larger, more preferably 10 nm or larger, even more preferably 15 nm or larger, and preferably 250 nm or smaller, more preferably 200 nm or smaller, and even more preferably 90 nm or smaller, from the viewpoint of the toner's chargeability, fluidity, and transferability.

[0100] External additive treatment, which involves mixing toner particles with external additives, can be carried out according to conventional methods, and a mixer such as a Henschel mixer can be used.

[0101] From the viewpoint of the toner's electrostatic properties, fluidity, and transferability, the content of the external additive is preferably 0.05 parts by mass or more, more preferably 0.1 parts by mass or more, even more preferably 0.3 parts by mass or more, and preferably 5 parts by mass or less, and more preferably 3 parts by mass or less, per 100 parts by mass of toner particles before treatment with the external additive.

[0102] The volume-intermediate particle size (D) of the toner of the present invention 50 The volume median particle size (D) is preferably 3 μm or more, more preferably 4 μm or more, and preferably 15 μm or less, more preferably 10 μm or less. 50 ) refers to the particle size at which the cumulative volume frequency calculated using volume fractions accounts for 50% when calculated from the smallest particle size. Furthermore, if the toner is treated with an external additive, the volume median particle size of the toner particles before treatment with the external additive is taken as the volume median particle size of the toner.

[0103] The toner of the present invention can be used as is as a one-component developing toner, or as a two-component developing toner used in combination with a carrier, in image forming apparatuses using either a one-component developing method or a two-component developing method, respectively. [Examples]

[0104] The present invention will be specifically described below with reference to examples, but the present invention is not limited in any way by these examples. The physical properties of resins, etc., can be measured by the following methods.

[0105] [Softening point of resin] Using a flow tester "CFT-500D" (manufactured by Shimadzu Corporation), 1 g of sample is heated at a heating rate of 6°C / min while a load of 1.96 MPa is applied by a plunger, and the sample is extruded from a nozzle with a diameter of 1 mm and a length of 1 mm. The amount of plunger descent of the flow tester is plotted against temperature, and the temperature at which half of the sample has flowed out is defined as the softening point.

[0106] [Maximum peak temperature of endothermic heat of resins and amide compounds] Using a differential scanning calorimeter "Q-100" (manufactured by T.A. Instruments Japan Co., Ltd.), 0.01 to 0.02 g of the sample is weighed into an aluminum pan, cooled from room temperature (25°C) at a rate of 10°C / min to 0°C, and maintained at 0°C for 1 minute. Then, measurements are taken at a rate of 10°C / min. Among the observed endothermic peaks, the temperature of the peak with the largest peak area is defined as the maximum endothermic peak temperature. For crystalline resins and amide compounds, the maximum endothermic peak temperature is defined as the melting point.

[0107] [Glass transition temperature of resins] Using a differential scanning calorimeter "Q-100" (manufactured by T.A. Instruments Japan Co., Ltd.), 0.01 to 0.02 g of the sample is weighed into an aluminum pan and heated from room temperature (20°C) to 200°C at a heating rate of 10°C / min, and then cooled to 0°C at a cooling rate of 10°C / min. Next, the sample is heated at a heating rate of 10°C / min and the endothermic peak is measured. The temperature at the intersection of the extension of the baseline below the maximum endothermic peak temperature and the tangent line showing the maximum slope from the rising part of the peak to the peak apex is defined as the glass transition temperature.

[0108] [Weight-average molecular weight of resins] The molecular weight distribution is measured by gel permeation chromatography (GPC) using the following method, and the weight-average molecular weight is determined. (1) Preparation of sample solution The sample is dissolved in tetrahydrofuran (amorphous resin) or chloroform (crystalline resin) at 40°C to a concentration of 0.5 g / 100 mL. Then, this solution is filtered using a PTFE type membrane filter "DISMIC-25JP" (manufactured by ADVANTEC) with a pore size of 0.20 μm to remove insoluble components and obtain the sample solution. (2) Molecular weight measurement Using the measurement apparatus and analytical column described below, tetrahydrofuran (amorphous resin) or chloroform (crystalline resin) is flowed as the eluent at a flow rate of 1 mL / min, and the column is stabilized in a constant temperature bath at 40°C. 100 μL of the sample solution is then injected, and the measurement is performed. The molecular weight of the sample is calculated based on a calibration curve prepared in advance. The calibration curve used in this case includes several types of monodisperse polystyrene (A-500 (5.0 × 10) manufactured by Tosoh Corporation). 2 ), A-1000 (1.01 x 10 3 ), A-2500 (2.63 x 10 3 ), A-5000 (5.97 x 10 3 ), F-1 (1.02×10 4 ), F-2 (1.81×10 4 ), F-4 (3.97×10 4 ), F-10 (9.64×10 4 ), F-20 (1.90×10 5 ), F-40 (4.27×10 5 ), F-80 (7.06×10 5 ), F-128 (1.09×10 6 The sample prepared using )) as a standard sample is used. The value in parentheses indicates the molecular weight. Measuring device: HLC-8220GPC (manufactured by Tosoh Corporation) Analysis column: TSKgel GMH XL +TSKgel G3000H XL (Manufactured by Tosoh Corporation)

[0109] [Melting point of release agent] Using a differential scanning calorimeter "Q-100" (manufactured by T.A. Instruments Japan Co., Ltd.), 0.02 g of the sample is weighed into an aluminum pan, heated to 200°C, and then cooled from 200°C to 0°C at a rate of 10°C / min. Next, the sample is heated at a rate of 10°C / min and the heat quantity is measured, with the maximum endothermic peak temperature being defined as the melting point.

[0110] [Average particle size of external additives] The average particle diameter refers to the number-average particle diameter, which is calculated by measuring the particle size (average of the major and minor axes) of 500 particles from scanning electron microscope (SEM) images and using the number-average value of these measurements.

[0111] [Toner volume medium particle size (D 50 )〕 • Measuring instrument: "Coulter Multisizer (Registered Trademark) III" (manufactured by Beckman Coulter, Inc.) • Aperture diameter: 50 μm • Analysis software: "Multisizer (registered trademark) III version 3.51" (manufactured by Beckman Coulter, Inc.) • Electrolyte: "Isoton (registered trademark) II" (manufactured by Beckman Coulter, Inc.) • Dispersion: Prepared by dissolving polyoxyethylene lauryl ether "Emulgen (registered trademark) 109P" [manufactured by Kao Corporation, HLB (Griffin) = 13.6] in the electrolyte to adjust the concentration to 5% by mass. • Dispersion conditions: Add 10 mg of the sample to 5 mL of the dispersion and disperse for 1 minute using an ultrasonic disperser (machine name: US-1 manufactured by SND Corporation, output: 80W). Then, add 25 mL of electrolyte and disperse for another minute using the ultrasonic disperser to prepare the sample dispersion. • Measurement conditions: The sample dispersion is added to 100 mL of the electrolyte to adjust the concentration so that the particle size of 30,000 particles can be measured in 20 seconds. Then, the 30,000 particles are measured, and the volume median particle size (D) is determined from the particle size distribution. 50 )

[0112] Resin manufacturing example 1 The alcohol components, carboxylic acid components other than adipic acid, esterification catalyst, and co-catalyst shown in Tables 1 and 2 were placed in a 10-liter four-necked flask equipped with a thermometer, stainless steel stirring rod, dehydration tube, condenser, and nitrogen inlet tube, and heated to 235°C over 2 hours in a mantle heater under a nitrogen atmosphere. After confirming that the reaction rate reached over 95% at 235°C, the mixture was cooled to 180°C, adipic acid was added, and the mixture was heated to 220°C over 2 hours. After reacting at 220°C for 1 hour, the reaction was carried out at 8 kPa until the softening point shown in Tables 1 and 2 was reached to obtain amorphous polyester resins (resins A1-A6, A8-A12). The mixture was then cooled to 180°C, the amide compounds shown in Tables 1 and 2 were added, and the mixture was melt-mixed at 180°C for 30 minutes to obtain mixtures of resin and amide compounds (mixtures 1-6, 8-12). The physical properties of the resins measured by taking a sample of the obtained resins are shown in Tables 1 and 2. In this specification, the reaction rate refers to the value of (mol) of reacted water produced / (mol) of theoretically produced water produced × 100.

[0113] Resin manufacturing example 2 The alcohol component, carboxylic acid components other than dodecenyl succinic anhydride, esterification catalyst, and co-catalyst shown in Table 1 were placed in a 10-liter four-necked flask equipped with a thermometer, stainless steel stirring rod, dehydration tube, condenser, and nitrogen inlet tube, and heated to 235°C over 2 hours in a mantle heater under a nitrogen atmosphere. After confirming that the reaction rate reached over 95% at 235°C, the mixture was cooled to 180°C, dodecenyl succinic anhydride was added, and the mixture was heated to 220°C over 2 hours. After reacting at 220°C for 1 hour, the reaction was carried out at 8 kPa until the softening point shown in Table 1 was reached to obtain amorphous polyester resin (resin A7). After cooling to 180°C, the amide compound shown in Table 1 was added, and the mixture was melt-mixed at 180°C for 30 minutes to obtain a mixture of resin and amide compound (mixture 7). The physical properties of the resin, measured by taking a sample of the obtained resin, are shown in Table 1.

[0114] Resin manufacturing example 3 The alcohol component, carboxylic acid components other than adipic acid and trimellitic anhydride, esterification catalyst, and co-catalyst shown in Table 2 were placed in a 10-liter four-necked flask equipped with a thermometer, stainless steel stirring rod, dehydration tube, condenser, and nitrogen inlet tube, and heated to 235°C over 2 hours in a mantle heater under a nitrogen atmosphere. After confirming that the reaction rate reached 95% or more at 235°C, the mixture was cooled to 180°C, and then adipic acid and trimellitic anhydride were added. The mixture was then heated to 220°C over 2 hours. After reacting at 220°C for 1 hour, the reaction was continued at 8 kPa until the softening point shown in Table 2 was reached, yielding an amorphous polyester resin (resin A13). The physical properties of the obtained resin are shown in Table 2.

[0115] Details of the amide compounds used are as follows: 12-Hydroxystearate ethylenebisamide: ITOHWAX J-530 (manufactured by Ito Oil Co., Ltd.), melting point 142℃ 12-Hexamethylenebisamide hydroxystearate: ITOHWAX J-630 (manufactured by Ito Oil Co., Ltd.), melting point 135℃ 12-Hydroxystearate xylylenebisamide: ITOHWAX J-700 (manufactured by Ito Oil Co., Ltd.), melting point 125℃ 12-Hydroxyethyl hydroxystearate: ITOHWAX J-420 (manufactured by Ito Oil Co., Ltd.), melting point 105℃ Ethylenebisamide stearate: Kao Wax EB-P (manufactured by Kao Corporation), melting point 143℃

[0116] [Table 1]

[0117] [Table 2]

[0118] Resin manufacturing example 4 The alcohol and carboxylic acid components shown in Table 3 were placed in a 10-liter four-necked flask equipped with a thermometer, stainless steel stirring rod, dehydration tube, condenser, and nitrogen inlet tube. The mixture was then kept at 140°C for 1 hour in a mantle heater under a nitrogen atmosphere, followed by a 10°C / h increase in temperature from 140°C to 200°C. A polycondensation reaction was then carried out at 200°C for 1 hour. Finally, the esterification catalyst shown in Table 3 was added, and the reaction was carried out at 200°C and 8 kPa until the softening point indicated in Table 3 was reached to obtain crystalline polyester resins (resins C1-C6).

[0119] [Table 3]

[0120] Examples 1-4, 7-18, Comparative Examples 1-3, 5-6 100 parts by mass of the mixture and resin shown in Table 4, 1 part by mass of the negative charge control agent "Bontron E-81" (manufactured by Orient Chemical Industry Co., Ltd.), the amount of the coloring agent "FASTOGEN SUPER MAGENTA R3-E" (manufactured by DIC Corporation, quinacridone pigment, CI Pigment Red 122 (PR122)) shown in Table 5, and 3 parts by mass of the release agent "HNP-9" (manufactured by Nippon Seiro Co., Ltd., paraffin wax, melting point: 75℃) were thoroughly mixed in a Henschel mixer. Then, using a twin-screw extruder with a total length of 1560 mm in the mixing section, a screw diameter of 42 mm, and a barrel inner diameter of 43 mm, the mixture was melt-kneaded at a roll rotation speed of 200 r / min and a heating temperature in the rolls of 100℃. The feed rate of the mixture was 20 kg / h, and the average residence time was approximately 18 seconds. The resulting kneaded material was cooled, coarsely ground, then ground in a jet mill, and classified to obtain the medium particle size (D) by volume. 50 ) yielded toner particles with a diameter of 8 μm.

[0121] To 100 parts by mass of the obtained toner particles, 1 part by mass of hydrophobic silica "AEROSIL NAX 50" (manufactured by Nippon Aerosil Co., Ltd., hydrophobic treatment agent: HMDS, average particle size: approximately 30 nm) was added as an external additive, and the mixture was combined in a Henschel mixer to obtain magenta toner.

[0122] Example 5 A magenta toner was obtained in the same manner as in Example 1, except that 8 parts by mass of "Ink Jet Magenta E5B02" (manufactured by Clariant, quinacridone-based pigment, CI Pigment Violet 19 (PV19)) was used as a coloring agent instead of "FASTOGEN SUPER MAGENTA R3-E".

[0123] Example 6 A magenta toner was obtained in the same manner as in Example 1, except that 8 parts by mass of "FASTOGEN SUPER RED 209 228-6736" (manufactured by DIC Corporation, quinacridone-based pigment, CI Pigment Red 209 (PR209)) was used as a coloring agent instead of "FASTOGEN SUPER MAGENTA R3-E".

[0124] Comparative Example 4 A magenta toner was obtained in the same manner as in Example 1, except that 8 parts by mass of "FUJI FAST CARMINE 520 (manufactured by Fuji Pigment Co., Ltd., naphthol-based pigment, CI Pigment Red 150 (PR150))" were used as a coloring agent instead of "FASTOGEN SUPER MAGENTA R3-E".

[0125] Test Example 1 [Printed Material Image Density] Toner was mounted on the non-magnetic single-component developer "COREFIDO C712dnw" (manufactured by OKI Electric Industry Co., Ltd.), and the toner adhesion amount was 0.40 mg / cm². 2 A solid image was printed on high-quality paper "J Paper A4 size" (manufactured by Fujifilm Business Innovation Co., Ltd.) without fixing it. Furthermore, the fuser of "COREFIDO C712dnw" (manufactured by Oki Electric Industry Co., Ltd.) was modified into an external fuser with a fixing speed of 100 mm / sec, and the fixing temperature was set to 170°C to fix the unfixed image. The reflective image density of the solid image portion of the printed material was measured using a colorimeter "SpectroEye" (manufactured by X-Rite, lighting conditions: standard light source D50, observation field of view 2°, density standard DINNB, absolute white standard), and the average of the values ​​measured at three arbitrary points on the image was used as the image density. The results are shown in Table 5. A higher value indicates better image density.

[0126] Test Example 2 [Weather Resistance of Printed Materials] White toner was installed in the non-magnetic single-component developer "COREFIDO C712dnw" (manufactured by OKI Electric Industry Co., Ltd.), and the toner adhesion amount was 0.40 mg / cm². 2 The resulting solid image was printed on high-quality paper "J Paper A4 size" (manufactured by Fujifilm Business Innovation Co., Ltd.) without fixing it. Furthermore, the fuser of the "COREFIDO C712dnw" (manufactured by Oki Electric Industry Co., Ltd.) was modified into an external fuser with a fixing speed of 100 mm / sec, and the fixing temperature was set to 170°C to fix the unfixed image.

[0127] The obtained fixed images were subjected to weather resistance testing using a xenon weatherometer under the following conditions.

[0128] • Irradiation test machine: SX75, manufactured by Suga Test Machine Co., Ltd. • Light source: Xenon lamp Filter: Inner = Quartz filter, Outer = #275 Panel temperature: 50℃ ·Battle humidity: 35~50%RH ·Irradiation intensity: 50 (W / m 2 ), measured values ​​at 300-400 (nm) • Cumulative illuminance: 40,000 (kJ / m 2 ), integrated value at 300-400 (nm)

[0129] Using a SpectroEye colorimeter (manufactured by X-Rite, lighting conditions: standard light source D50, observation field of view 2°, density reference DINNB, absolute white reference), the values ​​measured at three arbitrary points on the image were averaged, and the hue change amount ΔE was calculated based on the following formula. The results are shown in Table 5. A smaller hue change amount ΔE indicates better weather resistance.

[0130] ΔE=[(L * 1-L * 2) 2 +(a * 1-a * 2) 2 +(b * 1-b * 2)2 ] 1 / 2 L * 1, a * 1, b * 1: L before irradiation * a * b * value L * 2, a * 2, b * 2: L after irradiation * a * b * value

[0131] [Table 4]

[0132] [Table 5]

[0133] From the above results, it can be seen that the toners of Examples 1 to 18 produce images with excellent weather resistance, high image density, and excellent scratch resistance. In contrast, Comparative Example 1, which contains an amide compound without a hydroxyl group, and Comparative Examples 2 and 3, which do not contain a predetermined amount of a hydroxyl group-containing amide compound, exhibit insufficient weather resistance and image density. Furthermore, while Comparative Example 5, which contains too little quinacridone pigment, has good weather resistance, its image density is insufficient. Comparative Example 4, which contains a magenta pigment that is not a quinacridone pigment, and Comparative Example 6, which contains too much quinacridone pigment, have sufficient image density but lack weather resistance. [Industrial applicability]

[0134] The electrostatic image developing toner of the present invention is suitably used for developing latent images formed in electrostatic image developing methods, electrostatic recording methods, electrostatic printing methods, and the like.

Claims

1. A toner for developing electrostatic images, comprising a crystalline polyester resin, an amorphous polyester resin, a quinacridone pigment, and a hydroxyl group-containing amide compound, wherein the content of the quinacridone pigment is 4 parts by mass or more and 12 parts by mass or less per 100 parts by mass of the total amount of the crystalline polyester resin and the amorphous polyester resin, and the hydroxyl group-containing amide compound is of formula (I): R １ -CONH-X-NHCO-R ２ (I) (In the formula, R １ and R ２ Each of these is independently a hydroxyalkyl group having 12 to 22 carbon atoms, and X is a divalent hydrocarbon group having 2 to 12 carbon atoms. Or formula (II): R ３ -.ONH-R ４ (-I) (In the formula, R ３ R is a hydroxyalkyl group having 12 to 22 carbon atoms. ４ (This is a hydroxyalkyl group having 2 to 22 carbon atoms.) A toner for developing electrostatic images, wherein the compound represented by [formula] is such that the content of the hydroxyl group-containing amide compound is 0.4 parts by mass or more and 13 parts by mass or less, based on 100 parts by mass of the total amount of the crystalline polyester resin and the amorphous polyester resin.

2. The toner for developing electrostatic images according to claim 1, wherein the alcohol component of the crystalline polyester resin contains ethylene glycol.

3. The electrostatic image developing toner according to claim 1 or 2, wherein the carboxylic acid component of the crystalline polyester resin contains an aliphatic monocarboxylic acid compound having 12 to 30 carbon atoms.

4. Amorphous polyester resin, formula (III): 【Chemistry 1】 (wherein, OR ５ and R ５ O is an oxyalkylene group, R ５ is an ethylene group and / or a propylene group, x and y represent the average number of moles of alkylene oxide added, are each a positive number, and the value of the sum of x and y is 1 or more and 16 or less) The electrostatic image developing toner according to claim 1 or 2, comprising an amorphous polyester resin which is a polycondensate of an alcohol component and a carboxylic acid component, the alcohol component containing an alkylene oxide adduct of bisphenol A represented by [formula].

5. The toner for developing electrostatic images according to claim 1 or 2, wherein the quinacridone pigment contains C.I. Pigment Red 122.

Images