JPH03212654A - Magneta toner for electrophotogrpahy - Google Patents

Abstract

PURPOSE:To obtain a magenta toner for electrophotography controlling a hue and having a fine color and satisfactory weather resistance by adding an anthraquinone dye to a rhodamine dye belonging to C.I. Solvent Red 49. CONSTITUTION:A compd. having a structure represented by the formula as a rhodamine dye belonging to C.I. Solvent Red 49 and an anthraquinone dye are added to a binding resin, preferably styrene-acrylate resin. The pref. amt. of the rhodamine dye added is 3.0-6.0 pts. wt. per 100pts. wt. of the resin. The desirable ratio of the rhodamine dye to the anthraquinone dye is 10/1-6/10 and a lower ratio of the rhodamine dye brings lower saturation. In the case of 10/1-6/10 ratio, the chromaticity of a toner compsn. satisfies 50.0-80.0L*, 61.0-80.0a*, -10.0-40.0b* and 60.0-80.0c*. A magenta toner ensuring high saturation and vivid chromaticity, not coloring a silicone rubber roll and having superior light and heat resistances is obtd.

Description

DETAILED DESCRIPTION OF THE INVENTION Field of Industrial Application The present invention is a function color, full color, or multicolor electrophotographic toner, and provides a magenta toner for electrophotography that provides a clear color tone regardless of whether it is a -component method or a two-component method. Regarding.

Conventional technology The necessary conditions for a coloring agent for magenta toner for color electrophotography are: (1) It must have excellent spectral reflection properties (2) It must have excellent weather resistance (excellent light resistance and heat resistance) (3) Good compatibility with the binder resin (transparency) (4) No bleeding (5) Matching with the developing system of the copying machine (6) No toxicity There are things that don't exist.

Conventional magenta colorants for color electrophotography include rhodamine dyes and pigments and thioindigo pigments.

Quinacridone dyes and pigments, azo dyes and pigments, and other dyes and pigments are used. For example, ``Chiken No. 4946951'' describes quinacridone pigments,
No. 26574 describes a thioindigo pigment. However, any of these colorants may
It cannot be said that all of the characteristics of 11 to (6) are satisfied.

Further, azo dyes and pigments also had problems such as color turbidity, and their performance could not be said to be sufficient.

Problems to be Solved by the Invention Problems to be Solved by the Invention Problems to be Solved by the Invention
It was difficult to realize a magenta toner for electrophotography that solved the above problems with a magenta toner containing only the rhodamine dye of Olvent Red) 49.

The present invention uses anthraquinone dyes in combination with rhodamine dyes to control the hue, ensure brightness, especially bright chroma, and does not dye the silicone rubber roller, providing weather resistance (light resistance). The purpose of the present invention is to provide a magenta toner with excellent properties (e.g., heat resistance and heat resistance).

Means for Solving the Problems In order to solve the problems, the present invention provides a magenta for electrophotography which satisfies both the requirements of containing an anthraquinone dye in a rhodamine dye classified as C, 1, Solvent Red 49. It's toner. C, 1, Solvent
A compound classified as Red 49 is a compound having the following structure.

Anthraquinone dyes are specifically Mitsui Toatsu dyes.
It is TON-M-201 (product name) manufactured by Kogyo.

The amount of coloring agent added in the present invention is always a combination of the above two types,
The amount is 0.1 to 100 parts by weight of resin in total.
10.0 parts by weight is desirable, more preferably 3.0 to 6 parts by weight.
．． It is 0 parts by weight. If it is less than 0.1 parts by weight, coloring properties cannot be obtained and the concentration cannot be ensured, and if it is more than 10 parts by weight, the solubility of the dye in the resin decreases and problems such as bleeding are likely to occur.

The addition ratio of C,1, Solvent Red 49 dye and anthraquinone dye can be selected as appropriate depending on the target, but if the amount of C,1, Solvent Red 49 is extremely large, the color will take on a bluish tinge. This is not very preferable, and if anthraquinone dyes are present in an extremely large amount, the color saturation tends to decrease, which is not preferable. Preferably, C, 1, Solvent Red 49/Anthraquinone dye (TO
N-M-201 (trade name) is in the range of 10/1 to 6/10.

That is, with the above addition ratio, the chromaticity of the toner composition is
L*50.0~80. O, a*61.0-80.0. b
It is possible to satisfy *-10.0 to -40.0, C*60°0 to 80.0.

Note that all known binder resins can be used as the binder resin of the present invention. For example, polystyrene.

Poly-α-methylstyrene, chloropolystyrene, styrene-chlorostyrene copolymer, styrene-propylene copolymer, styrene-butadiene copolymer, styrene-
Vinyl chloride copolymer, styrene-vinyl acetate copolymer,
Styrene-maleic acid copolymer, styrene-acrylic ester copolymer, styrene-methacrylic ester copolymer, styrene-α-methyl chloroacrylate copolymer, styrene-acrylonitrile-acrylic ester copolymer, etc. Styrenic resin (monopolymer or copolymer containing styrene or styrene substitutes), epoxy resin, urethane-modified epoxy resin, silicone-modified epoxy resin, polyester resin, vinyl chloride resin, styrene-vinyl acetate copolymer, rosin modification Maleic acid resin, phenyl resin, polyethylene, polypropylene, ionomer resin, polyurethane resin, silicone resin.

Ketone resin, ethylene-ethyl acrylate copolymer,
Xylene resin, polyvinyl butyral resin, terpene resin, phenol resin, aliphatic or alicyclic hydrocarbon resin, etc. can be used alone or in combination. Particularly preferred in this case are styrene-acrylic ester resins, styrene-methacrylic ester resins, and polyester resins.

In addition, when using this developer as a two-component toner,
As the carrier, known carriers can be used. For example, surface-oxidized or unoxidized iron or iron and metals such as nickel, copper, zinc, cobalt, manganese, chromium, and rare earths, and alloys thereof, or oxides and ferrites can be used. Moreover, those whose surfaces are coated with various resins can also be used.

Depending on the case, a fluidity modifier such as colloidal silica may be added to the developer in an amount of 0.01 to 6.00 to the toner.
It may be added in an amount of approximately 0.1 to 1.0% by weight (particularly preferably 0.1 to 1.0% by weight).

A red dye classified as Effect C, 1, Solvent Red 49 exhibits a clear magenta color, but using this alone leaves some problems in weather resistance. Therefore, by combining it with an anthraquinone dye, it is possible to cover weather resistance while maintaining color saturation. Therefore, when printing is performed with a toner containing both of these, it is possible to obtain a clear magenta color.

Example 1 - 100 parts by weight of styrene-acrylic ester resin (trade name: Baier TBL-500, manufactured by Sanyo Chemical Co., Ltd.) - 4 parts by weight of polypropylene (trade name: Viscol 550-P, manufactured by Sanyo Chemical Co., Ltd.) - Charge control agent 2 Parts by weight (product name E-84, manufactured by Orient Chemical Co., Ltd.)・C,1, Solvent Red 49 5 parts by weight (product name Oil Pi
nk 312. (manufactured by Orient Chemical Co., Ltd.) - 1 part by weight of anthraquinone dye (product name TON-M-201, manufactured by Mitsui Toatsu Dye Co., Ltd.) The above materials were uniformly dispersed using a Henschel mixer, and the dispersion was melt-kneaded using a twin-screw extruder. After cooling, it was finely pulverized using a jet mill, and a classified product having an average particle size of 11 μm was obtained using a classifier.

Add hydrophobic silica (product name R97) to this classified product at 0.3%.
2, manufactured by Nippon Aerosil Co., Ltd.) was added externally using a Henschel mixer to obtain the magenta toner of the present invention. This toner was mixed with a ferrite carrier (FL-150, manufactured by Nippon Tetsuko Co., Ltd.) to form a developer. A laser printer (product name KX-P4450, manufactured by Matsushita Electric Industrial Co., Ltd.) using this developer
20,000 sheets were printed continuously.

The color of the resulting print was a clear magenta color that could be used as a magenta toner.

Sunshine Weather is used to check the light resistance of printed matter.
A 50-hour forced irradiation test was conducted using a meter, but no decrease in fading of magenta color was observed.

As for heat resistance, the sample was stored in a constant temperature bath at 50° C. for 12 days, but there was no deterioration in color and there were no problems with heat resistance. From these results, it can be judged that the weather resistance is excellent.

Example 2 - 100 parts by weight of saturated polyester resin (Polyester-HP-300, manufactured by Nippon Gosei Kagaku Kogyo Co., Ltd.) - 4 parts by weight of polypropylene (Viscol 550-P, manufactured by Sanyo Chemical Co., Ltd.) - Charge control agent
2 parts by weight (Bontron E-84.
Orient Chemical Co., Ltd.) ・C,1, Solvent Red 49 3 parts by weight (Oi
l Pink 312. (manufactured by Orient Chemical Co., Ltd.) - 2 parts by weight of anthraquinone dye (trade name TON-M-201, manufactured by Mitsui Toatsu Dye Co., Ltd.) The above material was made into a toner in the same manner as in Example 1, and the same evaluation test as in Example 1 was conducted. went. As a result, color, light resistance,
The results were fully satisfactory in terms of both heat resistance.

Example 3 - 100 parts by weight of styrene-acrylic acid ester resin (trade name: Hymer TB-1000, manufactured by Sanyo Chemical Co., Ltd.) - 4 parts by weight of polypropylene (trade name: Viscol 550-P, manufactured by Sanyo Chemical Co., Ltd.) - Charge control agent 4 Parts by weight (product name: Kaya Charge N-31, manufactured by Nippon Kayaku Co., Ltd.) - 2 parts by weight of C,1, Solvent Red 49 (product name: Oil Pink 812, manufactured by Orient Chemical Co., Ltd.) - 4 parts by weight of anthraquinone dye (product name: TON) -M-201, manufactured by Mitsui Toatsu Dyes Co., Ltd.) The above material was made into a toner in the same manner as in Example 1, and the same evaluation test as in Example 1 was conducted. As a result, the color, light resistance, and heat resistance were all sufficiently satisfactory.

Comparative Example Tostyrene-acrylic acid ester resin 100 parts by weight (trade name Hymer TB-1000, manufactured by Sanyo Chemical Co., Ltd.) - Polypropylene 4 parts by weight (trade name Viscole 550-P, manufactured by Sanyo Chemical Co., Ltd.) - Charge control agent 2 weight parts (Product name: Bontron E-84. Manufactured by Orient Chemical Co., Ltd.) ・C, 1, Solvent Red 49 5 weight m (Product name: Oil Pink 312. Manufactured by Orient Chemical Co., Ltd.) The above materials were made into a toner in the same manner as in Example 1, and carried out. The same evaluation test as in Example 1 was conducted. As a result, clear colors were obtained, but the light resistance was poor, and when comparing the printed image density in the Sunshine Weather Meter test, it was found to be 1.
The concentration of No. 60 decreased to 0.90 after 30 hours, which was a significant decrease in concentration.

Comparative Example 2 - Polyester resin 100 parts by weight (trade name Hymer ES-508, manufactured by Sanyo Chemical Co., Ltd.) - Polypropylene 2 parts by weight (trade name Viscole 550-P, manufactured by Sanyo Chemical Co., Ltd.) - Charge control agent 4 parts by weight (trade name Kaya Charge N-31 (manufactured by Nippon Kayaku Co., Ltd.) - Anthraquinone dye 6 parts by weight The above materials were made into a toner in the same manner as in Example 1, and the same evaluation tests as in Example 1 were conducted. As a result, although the light resistance and heat resistance were good, a clear color tone could not be obtained.

Effects of the Invention As is clear from the description of the examples above, by using the magenta toner of the present invention, a toner having good color tone and weather resistance can be obtained. It becomes possible to widely use it as a two-component developer, and even as a -component toner.

Claims (2)

[Claims] (1)C. I. A magenta toner for electrophotography characterized by containing both a rhodamine dye classified as Solvent Red 49 and an anthraquinone dye. (2) Chromaticity is L*50.0~80.0a*61.0~
80.0, b*-10.0~40.0, c*60.0~
The magenta toner for electrophotography according to claim 1, which satisfies both of 80.0.