toner

Abstract

To provide a toner that can prevent fogging and density unevenness.SOLUTION: A toner has a toner particle containing a binder resin. The toner particle contains a compound represented by a structural formula (1) and a compound represented by a structural formula (2). A content of the compound represented by the structural formula (2) in the toner is 0.3 mass ppm or more.SELECTED DRAWING: Figure 1

Description

[Technical Field]

[0001] This disclosure relates to toner used to develop an electrostatic latent image formed by methods such as electrophotography, electrostatic recording, and toner jet recording to form a toner image. [Background technology]

[0002] Electrophotographic technology, used in photocopiers, printers, and facsimile receivers, is facing increasingly stringent demands from users as the devices themselves have advanced. Recent trends show a growing use in advertising and design, requiring high color reproduction for output images. Therefore, there is a strong demand for toners used in image formation that offer expanded color gamuts and improved coloring capabilities.

[0003] As a colorant for yellow toner, a weather-resistant pigment containing the compound represented by the following structural formula (1) is preferred. [ka] Pigments containing the compound represented by structural formula (1) form intermolecular hydrogen bonds between carbonyl and imino groups, resulting in a strong crystalline structure in toner, and thus are considered to have excellent weather resistance. However, when pigments containing the compound represented by structural formula (1) are used as colorants, pigment aggregation due to hydrogen bonding is likely to occur, leading to a decrease in coloring power. As a means of improving coloring power, Patent Documents 1 and 2 disclose toners in which the pigment is treated with rosin acid to improve the dispersibility of the colorant. [Prior art documents] [Patent Documents]

[0004] [Patent Document 1] Japanese Patent Publication No. 2003-280246 [Patent Document 2] Japanese Patent Publication No. 2013-113981 [Overview of the Initiative]

Problems to be Solved by the Invention

[0005] According to the technology of the above document, abietic acid acts as a surfactant and the coloring power is improved. However, since abietic acid has a carboxy group, the hydrophilicity of the compound of Structural Formula (1) does not decrease. As a result, the compound of Structural Formula (1) with still high hydrophilicity adsorbs moisture particularly in a high temperature and high humidity environment, causing image defects such as fogging and density unevenness due to the difference in the rate of charge rise. The present disclosure provides a toner capable of suppressing image defects such as fogging and density unevenness even when a specific pigment is used in a high temperature and high humidity environment.

Means for Solving the Problems

[0006] The present disclosure relates to a toner having toner particles containing a binder resin, where the toner particles contain a compound represented by the following Structural Formula (1) and a compound represented by the following Structural Formula (2), and relates to a toner in which the content of the compound represented by the following Structural Formula (2) in the toner is 0.3 mass ppm or more.

Chemical Formula

Advantages of the Invention

[0007] According to the present disclosure, it is possible to provide a toner capable of suppressing image defects such as fogging and density unevenness even when a specific pigment is used in a high temperature and high humidity environment.

Brief Description of the Drawings

[0008] [Figure 1] Evaluation image of density unevenness

Modes for Carrying Out the Invention

[0009] In the present disclosure, descriptions such as "XX or more and YY or less" and "XX to YY" representing numerical ranges mean numerical ranges including the lower limit and the upper limit which are the endpoints, unless otherwise specified. When numerical ranges are described stepwise, the upper and lower limits of each numerical range can be arbitrarily combined.

[0010] Hereinafter, embodiments of the present disclosure will be specifically described. The present disclosure is a toner having toner particles containing a binder resin, where the toner particles contain a compound represented by the following structural formula (1) and a compound represented by the following structural formula (2), and relates to a toner in which the content of the compound represented by the following structural formula (2) in the toner is 0.3 mass ppm or more.

Chemical formula

[0011] The inventors have found that by containing at least the compound represented by structural formula (1) and the compound represented by structural formula (2) in the toner particles, fogging and density unevenness in a high-temperature and high-humidity environment can be suppressed. Regarding the detailed mechanism, the inventors think as follows.

[0012] The compound represented by structural formula (1) has polar groups such as an imino group and a carbonyl group in the molecule and is relatively hydrophilic. Therefore, a toner containing the compound represented by structural formula (1) is likely to adsorb moisture in the air in a high-temperature and high-humidity environment. By adsorbing moisture, the charge on the toner surface leaks and the charge amount decreases. This is considered to cause fogging and density unevenness. Even if rosin treatment is performed to improve the dispersibility of the pigment, since rosin acid has a carboxy group in the molecule, the hydrophilicity of the compound represented by structural formula (1) does not decrease and moisture adsorption occurs. However, by containing the compound represented by structural formula (2) in the toner particles, a decrease in charging can be suppressed and fogging and density unevenness can be suppressed.

[0013] The compound represented by structural formula (2) has a structure that readily interacts with the compound represented by structural formula (1), while having low molecular polarity and readily coexisting with the binder resin. Therefore, in the binder resin, the compound represented by structural formula (1) becomes more stable when it interacts with the compound represented by structural formula (2), and the presence of the less hydrophilic compound represented by structural formula (2) reduces the apparent hydrophilicity of the compound represented by structural formula (1). It is presumed that this inhibits moisture adsorption, thereby suppressing image defects such as haze and uneven density.

[0014] The content of the compound represented by structural formula (2) in the toner must be 0.3 ppm by mass or more. Only when the content of the compound represented by compound (2) is 0.3 ppm by mass or more will the effect of suppressing image defects such as fogging and density unevenness be achieved.

[0015] The preferred form of toner is described below. The content of the compound represented by structural formula (1) in the toner is preferably 0.5 to 10.0% by mass, more preferably 2.5 to 8.0% by mass, even more preferably 3.0 to 7.0% by mass, and even more preferably 4.0 to 6.0% by mass. By having a content of 0.5% by mass or more of the compound represented by structural formula (1), the coloring power and color can be further improved. On the other hand, by reducing the content of the compound represented by structural formula (1) to 10.0% by mass or less, the clouding and unevenness of concentration associated with the increased water adsorption by the compound represented by structural formula (1) can be further suppressed.

[0016] Furthermore, the content of the compound represented by structural formula (2) in the toner is preferably 0.5 to 10.0 ppm by mass, more preferably 1.0 to 7.0 ppm by mass, even more preferably 1.5 to 5.0 ppm by mass, and even more preferably 2.0 to 3.0 ppm by mass. By having a compound represented by structural formula (2) at a concentration of 0.5 ppm by mass or more, moisture adsorption in high-temperature, high-humidity environments can be further suppressed. On the other hand, by limiting the content of the compound represented by structural formula (2) to 10.0 ppm by mass or less, the interacting compound represented by structural formula (1) is prevented from localizing within the toner due to increased hydrophobicity, thereby maintaining better coloring power. The content of the compound represented by structural formula (2) can be controlled by the amount added.

[0017] Furthermore, the ratio (A) of the content of the compound represented by structural formula (1) in the toner to the content of the compound represented by structural formula (2) in the toner is preferably 5,000 to 100,000. More preferably 10,000 to 50,000, and even more preferably 15,000 to 30,000. By staying within the above range, the coloring power of the toner can be ensured while further suppressing the decrease in charge in high-humidity environments. (A) = Content of the compound represented by structural formula (1) / Content of the compound represented by structural formula (2)

[0018] Furthermore, the SP value of the binder resin is 9.5~10.6 (cal / cm²). 3 ) 0.5 Preferably, it is 9.6 to 10.0 (cal / cm²). 3 ) 0.5 That is the case. The SP value being within the above range allows structural formula (2) to maintain good affinity with the binder resin, making it easier for it to interact with the compound represented by structural formula (1).

[0019] Furthermore, it is preferable that the toner particles contain aluminum. The ratio (B) of the content of the compound represented by structural formula (1) in the toner to the content of the aluminum in the toner particles is preferably 3 to 105. More preferably, it is 4 to 70, even more preferably 4 to 60, and even more preferably 5 to 50. The aluminum content refers to the content of aluminum in the toner particles based on the mass of the toner. (B) = Content of the compound represented by structural formula (1) / Content of aluminum element

[0020] Aluminum has a relatively high ionization tendency and is easily ionized, so when the ratio (B) is 105 or less, aluminum ions efficiently coordinate to the compound represented by structural formula (1). This lowers the electron density of the aromatic ring of the compound represented by structural formula (1), causing it to interact more strongly with the compound represented by structural formula (2), resulting in a greater suppression of charge reduction. On the other hand, under conditions where the ratio (B) is 3 or higher, toner charge leakage by aluminum ions is suppressed, further reducing fogging and density unevenness.

[0021] While there are no particular limitations on the method for producing toner particles, methods for producing toner particles in an aqueous medium, such as suspension polymerization, emulsification and agglutination, are preferred from the viewpoint of efficiently incorporating the compound represented by structural formula (2) into the interior of the toner particles.

[0022] [Coloring agent] The compound represented by structural formula (1) is used as the yellow pigment. For example, CI Pigment Yellow 155, which contains the compound represented by structural formula (1) as its main component, can be used. The yellow pigment used in the toner may be treated with a processing agent. Furthermore, fatty acid metal salts or aromatic carboxylic acid metal salts may be used as pigment dispersants. For use as a pigment dispersant, aluminum compounds containing aluminum ions that readily coordinate to the compound represented by structural formula (1) are preferred, such as fatty acid metal salts or aromatic carboxylic acid metal salts.

[0023] In addition to the compound represented by structural formula (1), other pigments or dyes may be used as colorants. For example, yellow dyes such as CI Solvent Yellow 98 or CI Solvent Yellow 162 may be used in combination with the compound represented by structural formula (1). The content of colorants other than the compound represented by structural formula (1) is preferably 0.3 to 10.0 parts by mass, and more preferably 0.5 to 3.0 parts by mass, per 100 parts by mass of the binder resin.

[0024] [Additives] To provide a toner that can suppress image defects such as fogging and density unevenness in high-temperature and high-humidity environments, a compound represented by structural formula (2) is added. The compound represented by structural formula (2) may be a commercially available product; for example, it can be obtained as an isooctane solution of the compound represented by structural formula (2) (manufactured by Fuji Chemical Co., Ltd.).

[0025] [Charge control agent] Toner can also contain a charge control agent as needed. Known charge control agents can be used. Specific examples of compounds used as negative charge control agents include, for example, metal compounds of aromatic carboxylic acids such as salicylic acid, alkylsalicylic acid, dialkylsalicylic acid, naphthoic acid, and dicarboxylic acid, metal salts or metal complexes of azo dyes or azo pigments, boron compounds, silicon compounds, and calixarenes. Examples of positive charge control agents include quaternary ammonium salts, polymeric compounds having the quaternary ammonium salt in their side chains, guanidine compounds, nigrosine compounds, and imidazole compounds. The charge control agent may be used alone or in combination of two or more types.

[0026] Other charge control agents besides resin-based charge control agents include metal-containing salicylic acid-based and stearic acid-based compounds, with those containing aluminum or zirconium being particularly preferred. Particularly preferred control agents are salts of aluminum and a linear saturated fatty acid having 12 to 30 (preferably 16 to 24) carbon atoms, such as aluminum distearate. As a resin-based antistatic agent, it is preferable to use a polymer or copolymer having a sulfonic acid group, a sulfonic acid base or sulfonic acid ester group, a salicylic acid moiety, or a benzoic acid moiety. The amount of charge control agent added is preferably 0.01 parts by mass or more and 10.0 parts by mass or less, and more preferably 0.06 parts by mass or more and 1.2 parts by mass or less, per 100.0 parts by mass of the binder resin.

[0027] [Agglutinants] In toner manufacturing, flocculants may be used as needed. Additives that form complexes or similar bonds with the metal ions of the flocculant may also be used as needed. Chelating agents are preferably used as such additives. Examples of inorganic metal salts include metal salts such as calcium chloride, calcium nitrate, barium chloride, magnesium chloride, zinc chloride, aluminum chloride, and aluminum sulfate, as well as inorganic metal salt polymers such as polyaluminum chloride, polyaluminum hydroxide, and calcium polysulfide. As a chelating agent, a water-soluble chelating agent may be used. Examples of chelating agents include oxycarboxylic acids such as tartaric acid, citric acid, and gluconic acid, as well as iminodic acid (IDA), nitrilotriacetic acid (NTA), and ethylenediaminetetraacetic acid (EDTA). From the viewpoint of incorporating aluminum into toner particles, aluminum-containing flocculants such as aluminum chloride, aluminum sulfate, polyaluminum chloride, and polyaluminum hydroxide are preferred.

[0028] [Aluminum element] Toner particles preferably contain aluminum. Aluminum can be incorporated into the toner by using aluminum compounds in the charge control agent or flocculant, for example.

[0029] [Binding resin] The resin that can be used as the binder resin is not particularly limited, and resins conventionally used in toners can be used. Examples include polyester resins, vinyl resins, polyamide resins, furan resins, epoxy resins, xylene resins, and silicone resins.

[0030] Among these, the binder resin preferably contains at least one resin selected from the group consisting of vinyl resins and polyester resins. More preferably, it is a vinyl resin. The SP value of the binder resin is 9.5 to 10.6 (cal / cm²). 3 ) 0.5 It is preferable that this be the case. The toner particles may be toner particles with a core-shell structure having a core particle and a shell on the surface of the core particle. For example, it is preferable that the binder resin contained in the core particle is a vinyl resin, and the shell is a polyester resin.

[0031] Polymerizable monomers that can form vinyl resins include styrene monomers such as styrene, α-methylstyrene, and divinylbenzene; unsaturated carboxylic acid esters such as methyl acrylate, butyl acrylate, methyl methacrylate, 2-hydroxyethyl methacrylate, butyl methacrylate, and 2-ethylhexyl methacrylate; unsaturated carboxylic acids such as acrylic acid and methacrylic acid; unsaturated dicarboxylic acids such as maleic acid; unsaturated dicarboxylic acid anhydrides such as maleic acid anhydride; nitrile vinyl monomers such as acrylonitrile; halogen-containing vinyl monomers such as vinyl chloride; and nitro vinyl monomers such as nitrostyrene. These can be used individually or in combination. Preferably, it is a copolymer of a styrene monomer and an unsaturated carboxylic acid ester.

[0032] When using polyester resins, known polyester resins can be used. Specific examples include condensed polymers of dibasic acids and their derivatives (carboxylic acid halides, esters, acid anhydrides) and dihydric alcohols. If necessary, polybasic acids with a valency of three or higher and their derivatives (carboxylic acid halides, esters, acid anhydrides), monobasic acids, alcohols with a valency of three or higher, monohydric alcohols, etc., may also be used.

[0033] Examples of dibasic acids include aliphatic dibasic acids such as maleic acid, fumaric acid, itaconic acid, oxalic acid, malonic acid, succinic acid, dodecylsuccinic acid, dodecenylsuccinic acid, adipic acid, azelaic acid, sebacic acid, and decane-1,10-dicarboxylic acid; and aromatic dibasic acids such as phthalic acid, tetrahydrophthalic acid, hexahydrophthalic acid, tetrabromophthalic acid, tetrachlorophthalic acid, hetic acid, hymic acid, isophthalic acid, terephthalic acid, and 2,6-naphthalenedicarboxylic acid. Furthermore, examples of dibasic acid derivatives include carboxylic acid halides, esters, and acid anhydrides of the above-mentioned aliphatic dibasic acids and aromatic dibasic acids.

[0034] On the other hand, examples of dihydric alcohols include acyclic aliphatic diols such as ethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, diethylene glycol, dipropylene glycol, triethylene glycol, and neopentyl glycol; bisphenols such as bisphenol A and bisphenol F; alkylene oxide adducts of bisphenol A such as ethylene oxide adducts of bisphenol A and propylene oxide adducts of bisphenol A; aralkylene glycols such as xylylene diglycol; and isosorbide. Examples of polybasic acids with a valency of 3 or higher, and their anhydrides, include trimellitic acid, trimellitic anhydride, pyromellitic acid, and pyromellitic anhydride.

[0035] [wax] Toner particles preferably contain wax. Examples of waxes include the following: Hydrocarbon waxes such as low molecular weight polyethylene, low molecular weight polypropylene, alkylene copolymers, microcrystalline wax, paraffin wax, and Fischer-Tropsch wax; oxides of hydrocarbon waxes such as oxidized polyethylene wax or block copolymers thereof; waxes mainly composed of fatty acid esters such as carnauba wax; and deoxidized fatty acid esters such as deoxidized carnauba wax, which have been partially or completely deoxidized.

[0036] Furthermore, the following can be listed: saturated linear fatty acids such as palmitic acid, stearic acid, and montanic acid; unsaturated fatty acids such as brassic acid, eleostearic acid, and parinalic acid; saturated alcohols such as stearyl alcohol, aralkyl alcohol, behenyl alcohol, carnaubyl alcohol, ceryl alcohol, and melissyl alcohol; polyhydric alcohols such as sorbitol; esters of fatty acids such as palmitic acid, stearic acid, behenic acid, and montanic acid with alcohols such as stearyl alcohol, aralkyl alcohol, behenyl alcohol, carnaubyl alcohol, ceryl alcohol, and melissyl alcohol; fatty acid amides such as linoleic acid amide, oleic acid amide, and lauric acid amide; methylenebisstearate amide, ethylenebiscaprate amide, ethylenebislaurate amide, and hexamethylene Saturated fatty acid bisamides such as bis-stearamide; unsaturated fatty acid amides such as ethylenebisoleamide, hexamethylenebisoleamide, N,N'dioleyladipamide, and N,N'dioleylsebacamide; aromatic bisamides such as m-xylenebis-stearamide and N,N'distearylisophthalamide; fatty acid metal salts (commonly known as metal soaps) such as calcium stearate, calcium laurate, zinc stearate, and magnesium stearate; waxes grafted onto aliphatic hydrocarbon waxes with vinyl monomers such as styrene and acrylic acid; partially esterified fatty acids and polyhydric alcohols such as behenic acid monoglyceride; methyl ester compounds having hydroxyl groups obtained by hydrogenation of vegetable oils and fats. The wax content is preferably 0.5 parts by mass or more and 25 parts by mass or less per 100.0 parts by mass of the binder resin.

[0037] Furthermore, from the viewpoint of achieving both toner storage properties and resistance to high-temperature offset, it is preferable that the peak temperature of the maximum endothermic peak in the temperature range of 30°C to 200°C, as measured by a differential scanning calorimetry (DSC), be between 50°C and 110°C.

[0038] [Career] Toner may be used as a two-component developer when mixed with a magnetic carrier, as this provides stable images over a long period of time. As magnetic carriers, the following known materials can be used: iron powder with an oxidized surface, or unoxidized iron powder, metal particles such as iron, lithium, calcium, magnesium, nickel, copper, zinc, cobalt, manganese, chromium, and rare earth elements, their alloy particles, oxide particles, magnetic materials such as ferrite, and magnetic material dispersion resin carriers (so-called resin carriers) containing a magnetic material and a binder resin that holds the magnetic material in a dispersed state.

[0039] [Inorganic fine particles] The toner particles may be used as toner as is. Toner may also be obtained by adding various inorganic microparticles to the toner particles as needed. Examples of inorganic microparticles include the following: Silica, metal oxides (e.g., strontium titanate, cerium oxide, alumina, magnesium oxide, chromium oxide), nitrides (e.g., silicon nitride), metal salts (e.g., calcium sulfate, barium sulfate, calcium carbonate), fatty acid metal salts (e.g., zinc stearate, calcium stearate). The amount of inorganic fine particles as an external additive is preferably 0.5 to 5.0 parts by mass per 100 parts by mass of toner particles.

[0040] Inorganic microparticles can also be hydrophobized to improve toner fluidity and equalize the charge of toner particles. Examples of treatment agents for hydrophobizing inorganic microparticles include unmodified silicone varnish, various modified silicone varnishes, unmodified silicone oil, various modified silicone oils, silane compounds, silane coupling agents, other organosilicon compounds, and organotitanium compounds. These treatment agents may be used individually or in combination.

[0041] [Manufacturing method] The method for producing toner particles is not particularly limited and may be any known method, but suspension polymerization is preferred. For example, a polymerizable monomer composition is obtained by mixing a polymerizable monomer that produces a binder resin, a compound represented by structural formula (1), a compound represented by structural formula (2), and, if necessary, a compound containing an aluminum element, a mold release agent, other colorants, and other additives. Subsequently, this polymerizable monomer composition is added to a continuous phase (for example, an aqueous medium (which may contain a dispersion stabilizer if necessary)). Then, particles of the polymerizable monomer composition are formed in the continuous phase (aqueous medium), and the polymerizable monomers are polymerized. In this way, toner particles can be obtained.

[0042] The following describes methods for measuring various physical properties. <Identification and quantification of binder resins and colorants> The composition and ratio of constituent compounds such as resins and colorants contained in toner are identified using pyrolysis gas chromatography-mass spectrometry (hereinafter also referred to as "pyrolysis GC / MS") and NMR. If the resin contained in the toner is available separately, it can also be measured individually. Pyrolysis GC / MS is used to analyze the types of constituent compounds in resins. The resin is heated at 550°C~ The types of constituent compounds are identified by analyzing the mass spectrum of the components of the resin decomposition products generated when the resin is thermally decomposed at 700°C. The specific measurement conditions are as follows.

[0043] [Measurement conditions for pyrolysis GC / MS] Pyrolysis device: JPS-700 (Japan Analysis Industry) Decomposition temperature: 590℃ GC / MS instrument: Focus GC / ISQ (Thermo Fisher) Column: HP-5MS, length 60m, inner diameter 0.25mm, film thickness 0.25μm Inlet temperature: 200℃ Flow pressure: 100kPa Split: 50 mL / min MS ionization: EI Ion source temperature: 200℃ Mass range: 45-650

[0044] Next, the relative abundance of the constituent compounds of the identified resin was determined in the solid 1 Measurement and calculation are performed using 1H-NMR. Structural determination is performed using nuclear magnetic resonance spectroscopy. 1 The procedure is performed using 1H-NMR [400MHz, CDCl3, room temperature (25℃)]. Measuring device: FT NMR device JNM-EX400 (manufactured by JEOL Ltd.) Measurement frequency: 400MHz Pulse condition: 5.0 μs Frequency range: 10500Hz Total number of times: 1024 The molar ratio of each monomer component is determined from the integral values ​​of the obtained spectrum, and the composition ratio (mass%) is calculated based on this. The resin constituting 50% or more by mass of the toner is defined as the binder resin.

[0045] <Content of the compound represented by structural formula (2)> [Preparation of extracted samples] Add 18g of ethanol to 2g of toner and irradiate with ultrasound for 5 minutes. Then, let it stand in a 60°C constant temperature bath for 18 hours, and then let it stand at room temperature for 24 hours. Collect the supernatant and filter it through a PTFE syringe filter (250nm diameter), and use the filtrate as the measurement sample. [GC / MS analysis] GC:TRACE-1310 (manufactured by Thermo Fisher Scientific) MS:ISQ LT (manufactured by Thermo Fisher Scientific) Column: HP-5MS, 30m length x 250 μm inner diameter x 0.25 μm film thickness (manufactured by Agilent Technologies) Carrier gas: He gas (purity 99.99995%) Inlet temperature: 250℃ MS transfer line temperature: 250℃ MS ion source temperature: 250℃ MS ion source: EI (Electron Ionization Method) MS detection range (m / z): 45~800 GC column temperature: After holding at 40°C for 3 minutes, the column was heated to 300°C at a heating rate of 10°C / min. It was then held at 300°C for 1 minute. GC carrier gas flow rate: 1.5 mL / min Injection method: Split method, split ratio 1 / 1 Injection volume: 1.0μL Library: NIST

[0046] [Creating a calibration curve] A calibration curve was prepared using an isooctane solution of the compound represented by structural formula (2) (manufactured by Fuji Chemical Co., Ltd.) as a standard sample. Specifically, the standard sample was diluted with ethanol to five concentrations (0.10 ppm, 0.25 ppm, 0.54 ppm, 1.16 ppm, and 26.5 ppm), and the solutions were measured as samples for calibration curve preparation. The relationship between the peak area value and the concentration of structural formula (2) was plotted to obtain the calibration curve. The correlation coefficient was 0.992, showing good linearity. Subsequently, the sample was measured, and the content of the compound represented by structural formula (2) in the toner was calculated from the peak area value attributed to structural formula (2).

[0047] <Content of the compound represented by structural formula (1)> In calculating the content of the compound represented by structural formula (2) above, the content of the compound represented by structural formula (1) is calculated using a calibration curve prepared as follows. A calibration curve was created using CI Pigment Yellow 155 as the standard sample. Specifically, solutions of the standard sample diluted with ethanol at five concentrations (0.10%, 0.55%, 1.10%, 7.89%, and 15.7%) were measured as samples for calibration curve creation, and the relationship between the peak area value and the concentration of the compound represented by structural formula (1) was plotted to obtain the calibration curve. The correlation coefficient was 0.986, showing good linearity. Subsequently, the sample was measured, and the content of the compound represented by structural formula (1) in the toner was calculated from the peak area value attributed to structural formula (1).

[0048] <Method for measuring the content of aluminum element> The measurement equipment consists of the wavelength-dispersive X-ray fluorescence analyzer "ZSX Primus IV" (manufactured by Rigaku Corporation) and the accompanying dedicated software "ZSX" for setting measurement conditions and analyzing measurement data. The "Guidance" (manufactured by Rigaku Corporation) will be used. The anode of the X-ray tube will be Rh, the measurement atmosphere will be vacuum, the measurement diameter will be 30 mm, and the measurement time will be 20 seconds. Place an aluminum ring (40mm inner diameter, 43mm outer diameter, 5mm height) on the sample molding die of a semi-automatic MiniPress machine (manufactured by Specac). Place 3g of toner inside it. The material was placed inside and pressed and molded at a pressure of 15 tons for 1 minute to produce pellets for measurement. Pellets molded to a thickness of 3 mm and a diameter of 40 mm were used. Measurements are performed under the above conditions, and the elements are identified based on the peak positions of the obtained X-rays. The count rate (unit: cps), which is the number of X-ray photons per unit time, is then measured. At this time, the acceleration voltage and current values ​​of the X-ray generator are set to 32kV and 125mA, respectively. Furthermore, if aluminum-containing fine particles or other external additives are added to the toner particles, the external additives can be removed by a known method, and the resulting toner particles can then be measured using the method described above.

[0049] (Creation of a calibration curve for aluminum element) As a pellet for creating a calibration curve for determining the content, 0.001 part by mass of aluminum hydroxide Al(OH)3 is added to 100 parts by mass of a binder [trade name: Spectro Blend, components: C 81.0, O 2.9, H 13.5, N 2.6 (mass %), chemical formula: C 19 H 38 ON, shape: powder (44 μm); manufactured by Rigaku Corporation], and they are thoroughly mixed using a coffee mill, and pellets are prepared by pellet molding in the same manner as the above measurement pellets. Similarly, pellets are prepared by mixing and pellet molding such that the aluminum hydroxide is 0.005 part by mass, 0.01 part by mass, 0.05 part by mass, 0.1 part by mass, 0.5 part by mass, 1.0 part by mass, and 5.0 parts by mass, respectively. Taking the counting rate of the obtained X-rays on the vertical axis and the added concentration of aluminum element in each calibration curve sample on the horizontal axis, a calibration curve of a linear function is obtained. Based on the obtained calibration curve, the content of aluminum element contained in toner particles in the toner is calculated.

[0050] <Calculation method of SP value> The SP value is obtained as follows according to the calculation method proposed by Fedors. For each polymerizable monomer, for the atoms or atomic groups in the molecular structure, the evaporation energy (Δei) (cal / mol) and molar volume (Δvi) (cm 3 / mol) are obtained from the table described in "Polym. Eng. Sci, 14(2), 147 - 154(1974)", and (ΣΔei / ΣΔvi) 0.5 is taken as the SP value (cal / cm 3 ) 0.5 and so on. The SP value of the binder resin is obtained by obtaining the evaporation energy (Δei) and molar volume (Δvi) of the monomer units derived from the polymerizable monomers constituting the binder resin for each monomer unit, calculating the product with the molar ratio (j) of each monomer unit in the binder resin, respectively, and dividing the sum of the evaporation energies of each monomer unit by the sum of the molar volumes, and taking {(Σj×ΣΔei) / (Σj×ΣΔvi)} 0.5 as the SP value (cal / cm 3 ) 0.5 and so on.

[0051] <Method for measuring the weight-average particle size (D4) of toner particles> The weight-average particle size (D4) of toner particles is measured using the "Coulter Counter Multisizer 3" (registered trademark, manufactured by Beckman Coulter, Inc.), a precision particle size distribution analyzer using the pore electrical resistance method with a 100 μm aperture tube, and the accompanying dedicated software "Beckman Coulter Multisizer 3 Version 3.51" (manufactured by Beckman Coulter, Inc.) for setting measurement conditions and analyzing measurement data, with an effective measurement channel count of 25,000. The measurement data is then analyzed and calculated. The electrolytic aqueous solution used for measurement is prepared by dissolving special grade sodium chloride in deionized water to a concentration of approximately 1% by mass. For example, "ISOTON II" (manufactured by Beckman Coulter, Inc.) can be used. Before performing measurements and analysis, configure the dedicated software as follows.

[0052] In the "Change Standard Measurement Method (SOM)" screen of the dedicated software, set the total count in control mode to 50,000 particles, the number of measurements to 1, and the Kd value to the value obtained using "standard particle 10.0 μm" (manufactured by Beckman Coulter, Inc.). Press the threshold / noise level measurement button to automatically set the threshold and noise level. Also, set the current to 1,600 μA, the gain to 2, the electrolyte to ISOTON II, and check the box for flushing the aperture tube after measurement. In the dedicated software's "Pulse to Particle Size Conversion Settings Screen," set the bin spacing to logarithmic particle size, the particle size bins to 256 particle size bins, and the particle size range to 2 μm or more and 60 μm or less. The specific measurement method is as follows:

[0053] (1) Place approximately 200 mL of the electrolytic solution into a 250 mL round-bottom glass beaker specifically designed for the Multisizer 3, set it on the sample stand, and stir the mixture with the stirrer rod at 24 revolutions per second in a counterclockwise direction. Then, use the "Aperture Tube Flash" function of the dedicated software to remove any dirt and air bubbles from inside the aperture tube. (2) Place approximately 30 mL of the electrolytic aqueous solution into a 100 mL flat-bottomed glass beaker, and add approximately 0.3 mL of the following dilution as a dispersant. • Dilution solution: A 10% by mass aqueous solution of "Contaminon N" (a pH 7 neutral detergent for cleaning precision measuring instruments, consisting of a nonionic surfactant, anionic surfactant, and organic builder, manufactured by Wako Pure Chemical Industries, Ltd.) diluted three times by mass with deionized water. (3) Two oscillators with an oscillation frequency of 50 kHz are built in with their phases shifted by 180 degrees, and a predetermined amount of deionized water is placed in the water tank of the ultrasonic disperser described below, which has an electrical output of 120 W, and approximately 2 mL of the Contaminon N is added to this water tank. • Ultrasonic Dispersion System: "Ultrasonic Dispersion System Tetora150" (manufactured by Nikko Bios Co., Ltd.) (4) Place the beaker from (2) into the beaker fixing hole of the ultrasonic disperser and operate the ultrasonic disperser. Then, adjust the height of the beaker so that the resonance state of the liquid surface of the electrolytic aqueous solution inside the beaker is maximized. (5) While irradiating the electrolytic aqueous solution in the beaker described in (4) with ultrasound, add approximately 10 mg of toner to the electrolytic aqueous solution in small amounts and disperse it. Continue the ultrasonic dispersion treatment for another 60 seconds. During ultrasonic dispersion, adjust the water temperature in the tank to be between 15°C and 40°C as appropriate. (6) Using a pipette, the electrolytic aqueous solution (5) containing the dispersed toner is dropped into the round-bottom beaker (1) placed in the sample stand, and the concentration is adjusted to approximately 5%. The measurement is then continued until the number of particles reaches 50,000. (7) The measurement data is analyzed using the dedicated software attached to the device, and the weight-average particle size (D4) is calculated. Note that the "Average Diameter" on the Analysis / Volume Statistics (Arithmetic Mean) screen when the dedicated software is set to Graph / Volume % is the weight-average particle size (D4). [Examples]

[0054] The present invention will be described in more detail below with reference to examples. The present invention is not limited to the following examples. Unless otherwise specified, the parts and percentages in the following formulations are all based on mass.

[0055] <Manufacturing of polyester resin 1 for binding resins> In a reaction vessel equipped with a nitrogen inlet tube, a dewatering tube, a stirrer, and a thermocouple, the amounts of monomers shown in Table 1 were added, and then 1.5 parts of dibutyltin oxide were added as a catalyst per 100 parts of the total amount of monomer. Next, the temperature was rapidly raised to 180°C at atmospheric pressure under a nitrogen atmosphere, and then polycondensation was carried out by distilling off the water while heating from 180°C to 210°C at a rate of 10°C / hour. After reaching 210°C, the pressure inside the reaction vessel was reduced to 5 kPa or less, and polycondensation was carried out under conditions of 210°C and 5 kPa or less to obtain polyester resin 1.

[0056] <Manufacturing of polyester resin 2 for binding resins> Polyester resin 2 was manufactured using the same manufacturing method as polyester 1, except that the raw materials were changed as shown in Table 1. [Table 1] BPA-PO: Bisphenol A propylene oxide 2mol adduct The unit of SP value is (cal / cm). 3 ) 0.5 That is the case.

[0057] <Manufacturing of Toner 1> (Manufacturing of polyester resin A for shells) The following materials were added to an autoclave equipped with a vacuum device, water separator, nitrogen gas introduction device, temperature measuring device, and stirring device. Terephthalic acid 32.3 parts (50.0 mol%) • Bisphenol A-propylene oxide 2 molar adduct 67.7 parts (50.0 mol%) • Potassium titanium oxalate (catalyst) 0.02 parts Next, the reaction was carried out under a nitrogen atmosphere and atmospheric pressure at 220°C until the desired molecular weight was reached. After cooling, the mixture was pulverized to obtain polyester resin A for the shell.

[0058] (Preparation of dispersion) In a granulation tank, 100.0 parts of deionized water, 5.0 parts of sodium phosphate, and 0.8 parts of 10% by mass hydrochloric acid were added to prepare an aqueous sodium phosphate solution, which was then heated to 50°C. To this granulation tank, an aqueous calcium chloride solution prepared by dissolving 1.0 part of calcium chloride hexahydrate in 7.0 parts of deionized water was added, and the mixture was stirred for 30 minutes at a peripheral speed of 25 m / s using a TK homomixer (manufactured by Tokushu Kika Kogyo). This yielded a dispersion (aqueous dispersion) containing calcium phosphate fine particles as poorly water-soluble inorganic fine particles.

[0059] (Preparation of Pigment Dispersion Composition 1) • Polymerizable monomer (styrene): 50.0 parts • Coloring agent (CI Pigment Yellow 155): 6.0 parts • Compound represented by structural formula (2): 0.0003 parts • Aluminum distearate: 0.12 parts The above materials were introduced into an attritor (manufactured by Nippon Coke Co., Ltd.), and stirred at 200 rpm at 25°C for 180 minutes using zirconia beads with a radius of 1.25 mm to prepare pigment dispersion composition 1.

[0060] (Preparation of Pigment Dispersion Composition 2) Pigment dispersion composition 2 was prepared using the same preparation method as pigment dispersion composition 1, except that 0.0003 parts of dehydroabietic acid were added instead of the compound represented by structural formula (2).

[0061] (Preparation of colorant-containing composition 1) The following materials were placed in the same container and mixed and dispersed using a TK Homomixer (manufactured by Tokushu Kika Kogyo) at a peripheral speed of 20 m / s. Pigment dispersion composition 1: 56.1003 parts • Polymerizable monomer: Styrene: 20.0 parts • Polymerizable monomer: n-butyl acrylate: 30.0 parts • Coloring agent (CI Solvent Yellow 98): 1.0 part • Polyester resin A: 2.0 parts Crosslinking agent: Divinylbenzene: 0.5 parts Furthermore, after heating to 60°C, 9.0 parts of the release agent, behenyl behenate, were added, and the mixture was dispersed and mixed for 30 minutes to prepare colorant-containing composition 1.

[0062] (Preparation of toner particles 1) The above-mentioned colorant-containing composition 1 was added to a dispersion containing calcium phosphate fine particles and stirred at a peripheral speed of 30 m / s with a TK homomixer (trade name, manufactured by Tokushu Kika Kogyo) at a temperature of 60°C under a nitrogen atmosphere. To this, 9.0 parts of the polymerization initiator t-butyl peroxypivalate (manufactured by Nippon Oil & Fats Co., Ltd., trade name "Perbutyl PV", molecular weight: 174.2, 10-hour half-life temperature: 58°C) were added to prepare a dispersion containing polymerizable monomer composition particles. Next, the dispersion of the polymerizable monomer composition particles was transferred to another tank, and while stirring with a paddle agitator, the temperature was raised to 70°C. The mixture was reacted at 70°C for 5 hours, then the liquid temperature was raised to 82°C and the mixture was reacted for another 2 hours. After cooling, while maintaining stirring, dilute hydrochloric acid was added to dissolve the dispersion stabilizer until the pH reached 1.5. The solid components were filtered off, thoroughly washed with deionized water, and then vacuum-dried at 40°C for 24 hours to obtain toner particles 1 with a weight-average particle size (D4) of 6.8 μm.

[0063] (External addition process) For 100 parts of the toner particles 1 obtained from the above, hydrophobic silica (Nippon Aerosil Co., Ltd.) 1.5 parts of RY50 (manufactured by the company) were added and mixed using a Mitsui Henschel mixer (manufactured by Mitsui Miike Chemical Machinery Co., Ltd.). Then, the mixture was sieved using a vibrating sieve with a mesh size of 45 μm to obtain toner 1.

[0064] <Manufacturing of toners 2-3, 5, and 7-13> In the preparation of pigment dispersion composition 1 for toner 1, the amount of aluminum distearate, the compound represented by structural formula (2), was changed as shown in Table 2. Similarly, in the preparation of colorant-containing composition 1, toners 2-3, 5, and 7-13 were obtained by changing the amount of polymerizable monomer added. [Table 2] In Table 2, the amounts of styrene and n-butyl acrylate represent the amounts added to the pigment dispersion composition during the preparation of the colorant-containing composition. The amount of pigment represents the compound shown by structural formula (1).

[0065] <Manufacturing of Toner 14> In the preparation of the colorant-containing composition 1 of toner 1, toner 14 was obtained in the same manner except that pigment dispersion composition 1 was changed to pigment dispersion composition 2.

[0066] <Manufacturing of Toner 4> (Preparation of polyester resin particle dispersion) Polyester resin 1: 200.0 parts • Ion-exchanged water: 500.0 parts The above materials were placed in a stainless steel container and heated to 95°C in a warm bath to melt them. Using a homogenizer (IKA Ultra-Turrax T50), 0.1N sodium bicarbonate was added while stirring thoroughly at 7800 rpm to raise the pH above 7.0. Subsequently, a mixed solution of 3 parts sodium dodecylbenzenesulfonate and 297 parts deionized water was gradually added dropwise to emulsify and disperse, thereby obtaining a dispersion of polyester resin particles. When the particle size distribution of this polyester resin particle dispersion was measured using a particle size analyzer (Horiba, Ltd., LA-950), the number-average particle size of the contained polyester resin particles was 0.25 μm, and no coarse particles larger than 1 μm were observed.

[0067] (Preparation of wax particle dispersion) • Ion-exchanged water: 500.0 parts Behenyl behenate: 250.0 parts The above materials were placed in a stainless steel container and heated to 95°C in a warm bath to melt them. Using a homogenizer (IKA: Ultra-Turrax T50), 0.1N sodium bicarbonate was added while stirring thoroughly at 7800 rpm to raise the pH above 7.0. Subsequently, a mixed solution of 5 parts by mass of sodium dodecylbenzenesulfonate and 245 parts of deionized water was gradually added dropwise to emulsify and disperse the mixture. The particle size distribution of the wax particles contained in this wax particle dispersion was measured using a particle size analyzer (Horiba, Ltd., LA-920). The number-average particle size of the contained wax particles was 0.35 μm, and no coarse particles exceeding 1 μm were observed.

[0068] (Preparation of a dispersion of coloring agent particles) • Coloring agent (CI Pigment Yellow 155): 150.0 parts • Sodium dodecylbenzenesulfonate: 5.0 parts • Compound represented by structural formula (2): 0.0075 parts • Ion-exchanged water: 350.0 parts The above ingredients were mixed and dispersed using a sand grinder mill. The particle size distribution of the colorant particles contained in this dispersion was measured using a particle size analyzer (Horiba LA-920). The number-average particle size of the colorant particles contained was 0.2 μm, and no coarse particles larger than 1 μm were observed.

[0069] (Manufacturing of toner particles 4) • Polyester resin particle dispersion: 450.0 parts • Dispersion of coloring agent particles: 100.0 parts • Wax particle dispersion: 45.0 parts • Sodium dodecylbenzenesulfonate: 5.0 parts A dispersion of polyester resin particles, a dispersion of wax particles, and sodium dodecylbenzenesulfonate were charged into a reactor (1-liter flask with baffled anchor blades) and mixed uniformly. Meanwhile, a dispersion of coloring agent particles was uniformly mixed in a 500 mL beaker and gradually added to the reactor while stirring to obtain a mixed dispersion. While stirring the obtained mixed dispersion, 9.8 parts of an aqueous aluminum chloride solution was added dropwise as solid content to form aggregated particles. After the dropwise dispensing was complete, the system was purged with nitrogen and held at 50°C for 1 hour, followed by 55°C for another 1 hour. The temperature was then raised and maintained at 90°C for 30 minutes. After that, the temperature was lowered to 63°C and maintained for 3 hours to form fused particles. After the predetermined time, the mixture was cooled to room temperature (approximately 25°C) at a rate of 0.5°C per minute, washed, filtered, and separated into solid and liquid components, and then dried using a vacuum dryer to obtain toner particles 4. (External addition process) Toner 4 was obtained in the same manner as the external addition process for toner particles 1, except that the toner particles 4 described above were used.

[0070] <Manufacturing of Toner 6> In the preparation of the polyester resin particle dispersion for toner 4, polyester resin 1 was replaced with polyester resin 2. In the preparation of the colorant particle dispersion, the compound represented by structural formula (2) was changed to 0.0015 parts. Furthermore, in the toner particle manufacturing process, the polyester resin particle dispersion was changed to 420 parts, the colorant particle dispersion to 130 parts, and the added aluminum chloride aqueous solution as solid content to 12.8 parts, while all other steps remained the same to obtain toner 6.

[0071] <Manufacturing of Toner 15> (Preparation of dispersion) A magnesium chloride aqueous solution was prepared by dissolving 10.2 parts of magnesium chloride in 250.0 parts of deionized water in a granulation tank. To this granulation tank, an aqueous solution prepared by dissolving 6.2 parts of sodium hydroxide in 50.0 parts of deionized water was gradually added while stirring at a peripheral speed of 25 m / s using a TK homomixer (trade name, manufactured by Tokushu Kika Kogyo Co., Ltd.) to obtain a dispersion containing magnesium hydroxide (fine particles).

[0072] (Preparation of pigment dispersion composition 3) • Polymerizable monomer (styrene): 50.0 parts • Coloring agent (CI Pigment Yellow 155): 6.0 parts • Compound represented by structural formula (2): 0.00002 parts The above materials were introduced into an attritor (manufactured by Nippon Coke Co., Ltd.), and stirred at 200 rpm at 25°C for 180 minutes using zirconia beads with a radius of 1.25 mm to prepare pigment dispersion composition 3.

[0073] (Preparation of colorant-containing composition 3) The following materials were placed in the same container and mixed and dispersed at a peripheral speed of 20 m / s using a TK Homomixer (product name, manufactured by Tokushu Kika Kogyo). • 3 parts of the above pigment dispersion composition: 56.00002 parts • Polymerizable monomer: Styrene 20.0 parts • Polymerizable monomer: n-butyl acrylate 30.0 parts • Coloring agent (Solvent Yellow 98) 1.0 part • Electrostatic control agent: FCA-5 (product name, manufactured by Fujikura Chemical Co., Ltd.) 2.0 parts Crosslinking agent: Divinylbenzene 0.5 parts Furthermore, after heating to 60°C, 10.0 parts of the release agent, behenyl behenate, were added, and the mixture was dispersed and mixed for 30 minutes to prepare colorant-containing composition 3.

[0074] (Preparation of polymerizable monomer composition particles) The above-mentioned coloring agent-containing composition 3 was added to a dispersion containing magnesium hydroxide fine particles and stirred at a peripheral speed of 30 m / s with a TK homomixer (trade name, manufactured by Tokushu Kika Kogyo) at a temperature of 60°C under a nitrogen atmosphere. To this, 9.0 parts of the polymerization initiator t-butyl peroxypivalate (manufactured by Nippon Oil & Fats Co., Ltd., trade name "Perbutyl PV", molecular weight: 174.2, 10-hour half-life temperature: 58°C) were added to prepare a dispersion containing polymerizable monomer composition particles. Next, the dispersion of the polymerizable monomer composition particles was transferred to another tank, and the temperature was raised to 70°C while stirring with a paddle blade to carry out the polymerization reaction.

[0075] When the conversion rate of the polymerizable monomer reaches 95%, the temperature is raised to 90°C, and 2.0 parts of methyl methacrylate are dissolved as the polymerizable monomer for the shell, and 0.2 parts of 2,2'-azobis(N-butyl-2-methylpropionamide) are dissolved in 10 parts of ion-exchanged water as a water-soluble initiator. The solution was added. The polymerization reaction was carried out at 90°C for 3 hours to obtain a polymerization reaction solution (polymerization slurry) containing toner particles 1. After cooling, sulfuric acid was added to lower the pH to 6.5 or below, and the mixture was stirred for 2 hours to dissolve the poorly water-soluble inorganic fine particles on the surface of the toner particles. The dispersion of toner particles was filtered off, washed with water, and dried at 40°C for 48 hours to obtain toner particles 15 having a core-shell structure with a weight-average particle size (D4) of 6.8 μm.

[0076] (External addition process) 15 parts toner particles and 1.5 parts dry silica particles (AEROSIL® REA90, manufactured by Nippon Aerosil Co., Ltd.: positively charged hydrophobic silica particles) are mixed for 3 minutes using an FM mixer (manufactured by Nippon Coke Industries Co., Ltd.). Silica particles were attached to the material. Then, the material was sieved with a 300-mesh sieve (mesh opening 48 μm) to obtain toner 15.

[0077] <Physical properties of toners 1-15> The various physical properties described above were measured for toners 1 to 15, and the obtained properties are shown in Table 4. [Table 3]

[0078] <Overlap Rating> 300g of toner was left in a constant temperature bath at 40°C and 95% RH for 30 days, and the toner after this harsh exposure was evaluated. A Hewlett-Packard color laser beam printer (HP LaserJet Enterprise Color M652n) was used as the image forming apparatus, and it was modified to have a process speed of 300mm / sec. An HP 656X LaserJet toner cartridge (yellow) was used as the cartridge. The product toner was removed from inside the cartridge, cleaned with compressed air, and then 300g of the toner to be evaluated was filled in.

[0079] The toner was evaluated by performing the following tests using the above-mentioned cartridges. The above-mentioned cartridges were installed in the yellow station, and dummy cartridges were installed in the others for evaluation. Since toner 15 is a positively charged toner, various potential settings were changed to enable development of the positively charged toner. The evaluation conditions involved printing 30,000 images with an initial print density of 0.5% for horizontal lines under high temperature and high humidity conditions (temperature 32°C / humidity 85%RH). The reflectance (%) of the non-image area after the test was completed was measured using a "REFLECTOMETER MODEL TC-6DS" (manufactured by Tokyo Denshoku Co., Ltd.). The obtained reflectance was evaluated using the following criteria, subtracting it from the reflectance (%) of unused printout paper (standard paper) measured in the same manner. A smaller value indicates better suppression of image fringing. The evaluation was performed in gloss paper mode using plain paper (HP Brochure Paper 200g, Glossy, manufactured by HP, 200g / m²). 2 This was done using ). (Evaluation Criteria) A: Less than 0.5% B: 0.5% or more and less than 1.5% C: 1.5% or more and less than 3.0% D: 3.0% or more

[0080] <Uneven concentration> 300g of toner was left in a constant temperature chamber at 40°C and 95%RH for 30 days, and the toner after being subjected to harsh conditions was evaluated. The evaluation was performed by printing the image shown in Figure 2 under high temperature and high humidity conditions (temperature 32°C / humidity 85%RH) and evaluating the difference in image density between the solid image downstream of the printed area and the solid image downstream of the unprinted area. To measure image density, a Macbeth RD918 reflectance densitometer (manufactured by Macbeth Corporation) was used to measure the relative density of the white background area with a document density of 0.00 relative to the printout image. The transfer material is plain letter-sized paper (Xerox 4200, manufactured by Xerox, 75g / m²). 2 ) was used. (Evaluation Criteria) A: Less than 0.05 B: 0.05 or higher, less than 0.10 C: 0.10 or higher, less than 0.20 D:0.20 or more

[0081] <Image density> The toner's coloring power is comparable to that of a solid image (toner application rate: 0.4 mg / cm²). 2 The image density was evaluated based on the image density of the original document. A Macbeth RD918 reflectance densitometer (Macbeth Corporation) was used to measure the relative density of the printout image relative to the white background area with a document density of 0.00. The recording medium used was letter-sized plain paper (Xerox 4200, Xerox Corporation, 75 g / m²). 2 ) was used. (Evaluation Criteria) A: 1.40 or higher B: 1.20 or higher, less than 1.40 C: 1.00 or higher, less than 1.20 D: Less than 1.00

[0082] <Examples 1-15> In Examples 1 to 13, the above evaluation was performed using toners 1 to 13, respectively. The evaluation results are shown in Table 4.

[0083] <Comparative Examples 1 and 2> In Comparative Examples 1 and 2, the above evaluation was performed using toners 14 and 15, respectively. The evaluation results are shown in Table 4.

[0084] [Table 4]

[0085] This disclosure relates to the following configuration. (Composition 1) A toner having toner particles containing a binder resin, The toner particles contain a compound represented by the following structural formula (1) and a compound represented by the following structural formula (2), A toner characterized in that the content of the compound represented by the following structural formula (2) in the toner is 0.3 ppm by mass or more. TIFF0007853023000008.tif121168 (Configuration 2) The toner according to configuration 1, wherein the content of the compound represented by structural formula (1) in the toner is 0.5 to 10.0% by mass. (Composition 3) The toner according to configuration 1 or 2, wherein the content of the compound represented by structural formula (2) in the toner is 0.5 to 10.0 ppm by mass. (Composition 4) The toner according to any one of configurations 1 to 3, wherein the ratio (A) of the content of the compound represented by structural formula (1) in the toner to the content of the compound represented by structural formula (2) in the toner is 5,000 to 1,000,000. (A) = Content of the compound represented by structural formula (1) / Content of the compound represented by structural formula (2) (Composition 5) The SP value of the aforementioned binder resin is 9.5 to 10.6 (cal / cm²). 3 ) 0.5 The toner described in any of configurations 1 to 4. (Composition 6) The toner particles contain an aluminum element, The toner according to any one of configurations 1 to 5, wherein the ratio (B) of the content of the compound represented by structural formula (1) in the toner to the content of the aluminum element contained in the toner particles in the toner is 3 to 105. (B) = Content of the compound represented by the structural formula (1) / Content of the aluminum element (Composition 7) The toner according to any one of configurations 1 to 6, wherein the binder resin comprises at least one resin selected from the group consisting of vinyl resins and polyester resins.

Claims

1. A toner having toner particles containing a binder resin, The toner particles contain a compound represented by the following structural formula (1) and a compound represented by the following structural formula (2), A toner characterized in that the content of the compound represented by the following structural formula (2) in the toner is 0.3 ppm by mass or more.

2. The toner according to claim 1, wherein the content of the compound represented by the structural formula (1) in the toner is 0.5 to 10.0% by mass.

3. The toner according to claim 1 or 2, wherein the content of the compound represented by structural formula (2) in the toner is 0.5 to 10.0 ppm by mass.

4. The toner according to claim 1 or 2, wherein the ratio (A) of the content of the compound represented by structural formula (1) in the toner to the content of the compound represented by structural formula (2) in the toner is 5,000 to 1,000,000. (A) = Content of the compound represented by structural formula (1) / Content of the compound represented by structural formula (2)

5. The SP value of the aforementioned binder resin is 9.5 to 10.6 (cal / cm²). ３ ) ０．５ The toner according to claim 1 or 2.

6. The toner particles contain an aluminum element, The toner according to claim 1 or 2, wherein the ratio (B) of the content of the compound represented by structural formula (1) in the toner to the content of the aluminum element contained in the toner particles in the toner is 3 to 105. (B) = Content of the compound represented by the structural formula (1) / Content of the aluminum element

7. The toner according to claim 1 or 2, wherein the binder resin comprises at least one resin selected from the group consisting of vinyl resins and polyester resins.

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