JPS5979256A - Toner for developing electrostatic latent image - Google Patents

Abstract

PURPOSE:To obtain a toner stable in chargeability, long in life, and undergoing no unfavorable effect in tone by using a specified compd. as a charge controller. CONSTITUTION:The toner used here incorporates compds. represented by general formulae I , II, III in which X is H, K, Na, NH4, aliphatic ammonium, or alicyclic ammonium.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a toner for developing an electrostatic latent image formed by electrophotography, electrostatic recording, electrostatic printing, or the like.

For example, in the electrophotographic method, an electrostatic latent image is formed on the surface of a photoreceptor and then developed and transferred using a dry method. 〇 (Yo, due to repeated development due to continuous use, the 1tHJ of the copied image may change due to collisions between l-no particles and carrier particles, and mutual deterioration between them and the surface of the photoreceptor. ]
The quality of the copies increases and the quality of the copies deteriorates.

Furthermore, more toner increases the amount of toner (=J) attached to the surface of the photoreceptor that has an electrical latent image, increasing the copy density I!J
, usually increases by as much as 1 degree at the back end, resulting in the so-called fogging phenomenon.

Dry type 1-: As J-1, when 17 is marked as Kiria, 11 or (, 1) is used, and a 64-electrode control agent is usually used in 1 to 1.

The conventional charge control agent used in this scale is mainly dye-based, which has a complex structure and poor stability, and is decomposed or altered by mechanical, electrical, or optical impact, resulting in charge control. 9i1 characteristics are easily lost. Furthermore, a significant drawback of conventional dye-based charge control agents is their colored nature. Rinawa 4),
Conventional dyes are suitable for use in monochrome and non-color applications, but demand for full-color copiers and two-color copies such as black and red, for which demand has been increasing in recent years, has increased.
No significant deterioration of tone occurs when applied to Colors 1 to 1.

The present invention solves the above-mentioned conventional problem of viscosity. Therefore, the present invention is a 1-ner which charges the carrier to Ω polarity,
The charge is stable and the color tone is not adversely affected.

Of course, the present invention provides a tonneau for electrostatic latent images comprising at least resin J3 and a colorant, which is based on the general formula (a).
It has been discovered that at least one of the compounds represented by (c) shows excellent properties as a charge control agent.

Specific examples of compounds corresponding to general formula (a) are shown in the notes.

...(a)-[11 As a synthesis example of such a compound, compound (a)-(11) is shown below.

Synthesis Example 1 18.8 g of 1-hydroxy-2-naphtho-1 acid was dissolved in 250 mβ of methanol, 24.5 g of a 40% aqueous chromic sulfate solution was added, and a 25% aqueous sodium hydroxide solution was added. -1 was adjusted to about 5. After stirring this solution under reflux for 3 hours, the precipitated crystals were collected by filtration and 1%
After washing with an aqueous sulfuric acid solution, washing with water at 500m℃ three times and then once with methanol 400111J2 (a)-
A chromium complex of 111 was obtained.

Eleven examples of compounds corresponding to general formula (b) are shown below.

...... (mouth) - (sword...1) -13j An example of the synthesis of such a compound is compound (b) - (1) (according to Juki).

Synthesis Example 2 2-Human [, 1 Sea 1-Boo 71-1 acid 18,8 (
Dissolve 250ml of methanol and ffi, add 24.5ml of 40% aqueous chromic sulfate solution, and add 25ml of 40% aqueous chromic sulfate solution to
% aqueous sodium hydroxide solution was added to adjust pl-1 to about 5.

This liquid was stirred under reflux for 3 #1, then concentrated, and the residue was washed with 500 rrl β of water. Then, after washing with a 1% aqueous sulfuric acid solution, washing with water 5 (Hl mρ) three times and then once with methanol 400 m12 (b) remove the chromium complex of dll, which corresponds to the general formula (c). If specific examples of the compounds are not shown, they are as follows.

......(c)-[11...(c)i21...(c)-+31 Synthesis examples of such compounds are as follows for compound (c)-(1). Please accept the following.

Synthesis Example 3 2-Human['xy-3naph 1-di acid 18,8 (J) was dissolved in methanol 250mρ, and to this solution was added 24.5% of a 40% aqueous chromic sulfate solution to give 25% hydroxy- In addition to Nori~lium aqueous solution, 11+1 was adjusted to about 5.

This solution was stirred until 17 il, concentrated, and the residue was washed with 300 mρ of water. After washing with C1% sulfuric acid aqueous solution, rinse with water at 500 rnA.
3 times and then once with 400 mJ2 of methanol to obtain 1 g of (c)-(1) paste 11m button rest.

Electrical latent image 1 according to the present invention! The toner for A image can be obtained by combining one or more of the charge control agents mentioned above and mixing the toner components with 8". Within this range, charge controllability can be stably exhibited over a long period of time.

As the vine binder resin used in the present invention, it is preferable to use almost all 4ifl resins that have been conventionally used in the past.

For example, small polymers of styrene and its substituted products such as polystyrene, poly(1)-chlorostyrene, and polyvinyl-1-helene, styrene-1)chlorostyrene polymers, styrene-pyrene polymers, and styrene-vinyltolene polymers. Car coalescence, styrene-butylene acrylate copolymer, styrene-methylene acrylate copolymer, styrene-acetyl acrylate copolymer, styrene-methacrylate copolymer, styrene-edyl methacrylate copolymer , styrene-butyl methacrylate copolymer, styrene-alpha chloromethyl methacrylate copolymer, styrene-acrylic L to 1
-lyl copolymer, styrene-vinyl methyl 1-del copolymer, styrene-vinylethyl 1-thyl copolymer, styrene-vinyl methyl lactone copolymer, styrene-j-di-1 copolymer, styrene-isoprene Styrenic copolymers such as copolymers, polymethylmethacrylate-1~, polybutylmethacrylate-1~, vinyl-based polymers such as polyvinyl chloride, polyacid-resistant vinyl, polystyrene, polypropylene, and other Borini L Sprue, polyurethane, polyamide, 1-boxy resin, rosin, modified rosin, Derben resin, phenol resin, aliphatic or alicyclic hydrocarbon resin, aromatic petroleum resin, chlorinated paraffin, paraffin wax, etc. 111 Germany or! IX, used appropriately (
I can do it.

In addition to the resin, the hue is adjusted from 1 to 1 in the explanation.
1i1-! To achieve this, various dyes, pigments, or colorants are added as colorants.

They include carbon black, aniline black, Ahiboolen black, Yellow 1 (), Kado 49641 day-,
Hansa Yellow G1 Benzidine Yellow 01 Quinoline Yellow L', I-G, Red] Yellow lead, Palcan Orange, Indanthrene Brilliant 1~Orange, Pencil, Cadmium Red, Lysole Red, Pyran [1 Red,
Brilliant 1-Carmine 6B1 [21-Tamine Lake B17 As 1 ~ Violet B1 State Portrait, Kobal 1-Blue, Hifu 1 ~ Rear Blue Lake, Lid 1'' 1 Cyanine Blue, Heat Metal Phthalocyanin Blue, Oxidized L1 Mu,
Makkai 1 - green lake, zinc white, titanium oxide, Murai 1 - powder, clay, silica, alumina, etc.

Next, the present invention will be described in detail with examples.

Example 1 Try -C tree for the following formulation ('l L/　/ko.

Styrene-11-bubur methacrylate-1-copolymer
100 parts by weight Mashibon Black
10 parts by weight) Compound of example (a) 11)
2 parts by weight of the obtained Iζ toner were mixed with the iron powder carrier of the 5th wheel hanging section and the 95th wheel hanging section to prepare a developer.

Measure the amount of charge on the 1-ner at B:J--47 Charge M measurement position C! ζ becomes -15μc/q, i-pole 1 (1
It turns out that it is controlled by = (.

Apply this developer to the FL-6200, which is a copy of this developer, and perform continuous -1 piece 1-/, -, 2
Charge amount after 75 sheets (.&-10μC/(l or more)
It was confirmed that the charging was stable.

Comparative Example 1 The compound of structure example (1) [,), but with the exception of the unadded steel, the fruit color tone 'l was made using the same method as 1-ner (81),
Current 1qA agent 1! ) Iko.

Measure the amount of charge from 1 to Boo, +1.3μC
/ It was almost completely charged.

A blue color 1-boo was prototyped in the process Ij of Example-1.
.

Sudilene-n butyl methacrylate-1/J (polymer 100 Shigekawa Shigekawa talocyanine pur = (Bigmen 1 to Blue 15) 2 parts by weight of compound [11] of structure example (a) obtained l
The amount of charge was measured by mixing the toner with 5 layers and 9 and 1 layer of ♀ powder and measuring the amount of charge as a developer.-15
μC/g is controlled to negative polarity.1. , :.

Next, use this developer as our company's Duplex I [Double G20]
I got a 1-sea bee at 0. The density of toner 1 was measured using blue, green, and red filters, and the efficiency (E Hiciency) specified in IZ was determined to be 70%.

H: 3-color filter ii' 1 degree maximum dark melon M: medium, 1-: minimum temperature 1 good (E ff1c: ancy is ＾ culm fin color (eroded)) This is a structural example ( b) 1 that does not contain the compound of (1)
- There is no difference from the value of 70% in the case of no image, and the present developer has no adverse effect on the color tone.

Understood.

Example 33 1.92! , /J produced a prototype of the color i-boo.

Jubo 1-shi resin (Toto Kasei YD 017) 1 (1
(l car m part j Lillian 1-Carmine 6F3 5 weight part J(?1
Light control (a)]2) Compound 2 wheel 7β part Example 1
When I measured the amount of C charge on Dol1ffi1, it was -20
μC/Li... Example 4 47 of Example 1. j In place of the compound in (1) of Situation (A), 1' 4fli i The compound of (2) in Opening (A) was used, and the other conditions were exactly the same as those in Example 1. Henner charge ω is -18μC/(lt”,
2 pieces - 11 - L) - 15IIC/g or more IC Atsulko.

Example 55 In place of the compound (1) in Example 48 (a) of Example 1, (
(B) Except for using the compound in (1), the procedure was carried out in exactly the same manner as in Example 1, and the same results were obtained.

Comparative Example 2 Comparative Examples 1 to 1 were prepared in exactly the same manner as in Example 5, except that the compound (1) in Structural Example (B) was not added, and 1 g of developer was used. When we measured the amount of charge on the toner, it was +1.3μ.
It wasn't as charged as C/.

Example 6 The same procedure as in Example 2 was carried out except that (1) in Structure Example (B) was used in place of (1) in Example (A). It's late.

Example 7 The same results were obtained using the compound (2) of the structural example (['') instead of the compound (2) of the structural example (a) of Example 3.

Example 8 The same results as in Example 1 were obtained by using the compound of IM 3^ Example (B) (2) in place of Structural Example (A) (2) of Example 4.

Example 9 The compound of (c) (1) was used in place of the compound of structural example (a) of 11) of Example 1, and the same procedure was carried out except for /=, and the same results as in Example 1 were obtained. is 1η 1. , :
,.

Comparative example 3 4.1. j jlJ, 1-ner was prepared in exactly the same manner as in Example 9 except that the compound (1) of Example (c) was not added, and the current t'A agent was 141k. When the amount of charge was measured for 1 to 3, it was found to be +1.3 μC/CI, which was hardly any charge.

Example 10 The procedure was carried out in exactly the same manner as in Example 2, except that (1) of IM structure example C) was used in place of (1) of IM structure example A) of Example 2, and the results were the same as in Example 2! 2 is 1;

Fruit/11! ! Example 11 tj, l of Example 33 A similar result was obtained by using the compound of structure example (c) (2) instead of the compound of structure (c) (2).

Example 12 When the compound of structure example (c) (2) was used in place of IFJ Jlla example (a) (2) of Example 4, Example 4
I got similar results.

Claims (1)

[Scope of Claims] +1) The electrostatic latent image developing agent 1 to 1 consisting of at least Wood 1117 J3 and a colorant contains at least one of the compounds represented by the following general formulas (A) to (C). Characteristic 1-ner for developing electrostatic latent images. General formula % Formula % () () However, in the formula, X represents any of Na, N, I4, aliphatic ammonium, alicyclic ammonium, and heterocyclic ammonium