WO2015020165A1

WO2015020165A1 - Powder, method for preventing agglomeration of powder, and method for improving dyeing properties

Info

Publication number: WO2015020165A1
Application number: PCT/JP2014/070928
Authority: WO
Inventors: 諒寺西; 慎介清水; 鈴木　祐司
Original assignee: 日本化薬株式会社
Priority date: 2013-08-09
Filing date: 2014-08-07
Publication date: 2015-02-12
Also published as: JPWO2015020165A1

Abstract

[Problem] The present invention addresses the problem of providing: a powder of a resin composition comprising at least a resin and two types of dyes; a method for preventing powder agglomeration in the powder of the resin composition; and a method for improving dyeing properties in a dyeing method using the powder of the resin composition as a coloring agent. [Solution] A powder of a resin composition comprising at least a resin and two types of dyes, wherein at least one of the two types of dyes is a disperse or oil-soluble dye of which the solubility in propylene glycol monomethyl ether acetate is 0.04 to 20 g/100 ml.

Description

Powder, method for suppressing powder aggregation and method for improving dyeability

The present invention relates to a powder of a resin composition containing at least a resin and a dye, a method of suppressing powder aggregation in the powder of the resin composition, and a method of improving dyeability in the powder of the resin composition.

The powder of the resin composition containing the dye is, for example, as a coloring material, various inks such as ultraviolet curable ink, thermosetting ink, inkjet ink, gravure ink, offset ink, liquid toner, transfer type silver halide photosensitive material. It is used in various fields such as thermal transfer recording materials, recording pens, optical recording medium materials, adhesives, powder paints, powder toners and the like.
Examples of the colorant contained in these powders include various pigments and dyes. However, the resin composition powder containing a disperse dye or oil-soluble dye as a colorant is different from other colorants, for example, during transportation, when used as a coloring material, due to long-term storage or change over time, etc. In particular, since it has been known that powder agglomeration occurs at high temperatures, the suppression thereof is an extremely important issue.
This powder agglomeration is caused by the fact that the dye that has been uniformly melted or dispersed in the resin composition is likely to become non-uniform due to heat and come out on the surface of the resin composition. It was suggested that it is caused by chemical or chemical interaction. When such agglomeration occurs, various physical properties such as the fluidity, dispersibility, and charging property of the powder are impaired. Therefore, suppression of the agglomeration is strongly demanded.

Examples of the dyeing method using a resin composition powder containing these dyes as a colorant include, for example, an ink-jet dyeing method using an ink-jet ink, and an electrophotographic method using a dry powder toner or liquid toner. Examples include dyeing methods.
In the dyeing method using the resin composition powder containing a dye as a colorant as described above, it is known that defects are likely to occur in the dyeability of the dyed product such as white background contamination, density unevenness, and dyeing unevenness. ing. The reason for this is not clear, but in the case of resin composition powder containing a dye, when it is exposed to high temperatures during transportation and use, it tends to cause poorer dyeability. It is speculated that some physical property change occurs in the powder, which is the cause.
Such a dyeing defect is not observed in the powder of the resin composition containing the pigment, and is a phenomenon peculiar to the powder containing the dye. Therefore, the improvement in the powder containing the dye is extremely important. It is a difficult task.

Patent Document 1 discloses a colorant fine particle dispersion prepared from a hydrophobic colorant selected from oil-soluble dyes and disperse dyes and a rosin compound that is a natural resin, as a raw material for water-based inkjet recording inks.
Further, as dry powder toners and liquid toners used in the electrophotographic method, for example, Patent Documents 2 to 5 disclose various types.
Sublimation transfer dyeing using an electrophotographic method is disclosed, for example, in Patent Documents 6 to 11 below.

JP-A-8-34941 JP 2012-1829 A Japanese Patent Laid-Open No. 5-27474 Japanese Unexamined Patent Publication No. 9-73198 Japanese Patent Laid-Open No. 3-18866 Japanese Patent Laid-Open No. 02-295787 Japanese Patent Laid-Open No. 06-055991 Japanese Patent Laid-Open No. 10-058638 JP 2000-029238 A Special Table 2006-500602 JP 2011-100129 A

The present invention uses a powder of a resin composition containing at least a resin and two types of dyes, a method for suppressing powder aggregation in the powder of the resin composition, and the powder of the resin composition as a colorant. It is an object of the present invention to provide a method for improving dyeability in a dyeing method.

As a result of intensive studies to solve the above problems, the present inventors have found that at least one of the two types of dyes is contained in the powder of the resin composition containing at least a resin and two types of dyes. The present invention has been completed by finding that the above-mentioned problems can be solved by using a disperse dye or oil-soluble dye having a solubility in propylene glycol monomethyl ether acetate of 0.04 g / 100 ml to 20 g / 100 ml. That is, the present invention relates to the following (1) to (13).

(1) A powder of a resin composition containing at least a resin and two types of dyes, wherein at least one of the two types of dyes has a solubility in propylene glycol monomethyl ether acetate of 0.04 g / A powder which is a disperse dye or an oil-soluble dye of 100 ml to 20 g / 100 ml.
(2) Of the at least two dyes, the at least one dye is a disperse dye or oil-soluble dye having a solubility in propylene glycol monomethyl ether acetate of 0.04 g / 100 ml to 20 g / 100 ml, and the at least one dye The powder according to (1) above, wherein the other type of dye is a dye selected from the group of oil-soluble dyes consisting of disperse dyes, basic dyes, vat dyes, and solvent dyes.
(3) Among the at least two kinds of dyes, the at least one kind of dye is a dye selected from anthraquinone series, quinophthalone series, and azo series compounds,
The at least one other dye is an anthraquinone, azo, azomethine, indophenol, indoaniline, pyrroline, quinophthalone, naphthalimide compound, disperse dye, basic dye, The powder according to (1) or (2) above, which is a dye selected from the group of oil-soluble dyes consisting of vat dyes and solvent dyes.
(4) Any one of the above (1) to (3), wherein the at least one other dye is a dye selected from the group of oil-soluble dyes consisting of disperse dyes, basic dyes, and solvent dyes The powder described in.
(5) The powder of the resin composition according to any one of (1) to (4), which is used for suppressing powder aggregation or used as a colorant in a method for improving dyeability.
(6) A toner containing the powder of the resin composition according to any one of (1) to (4) above, at least a charge control agent, a wax, and an external additive.
(7) The toner according to (6), which is used for suppressing powder aggregation or used as a colorant in a method for improving dyeability.
(8) A method for suppressing powder aggregation in the powder of the resin composition according to any one of (1) to (4) above.
(9) A method for improving dyeability in a dyeing method using the powder of the resin composition according to any one of (1) to (4) as a colorant.
(10) A dyeing method using the powder of the resin composition according to any one of (1) to (4) above.
(11) A substance stained by the staining method described in (10) above.
(12) In the dyeing method using the resin composition powder as a colorant, the resin composition powder is adhered to an intermediate recording medium by an electrophotographic method, and the resin composition powder is adhered to the intermediate recording medium. The method for improving dyeability according to the above (9), which is a sublimation transfer dyeing method in which dyeing is performed by sublimating and transferring a dye contained in a body to an object to be dyed.
(13) An intermediate recording medium in which the powder of the resin composition is adhered by an electrophotographic method in the method for improving dyeability according to the above (12).

According to the present invention, a powder of a resin composition containing at least a resin and two kinds of dyes, a method for suppressing powder aggregation in the powder of the resin composition, and dyeing using the powder of the resin composition as a colorant A method for improving dyeability in a method is provided.

Hereinafter, the present invention will be described in detail. Unless otherwise specified, in this specification, “parts” means parts by mass, and “%” means mass%, including examples.
The present invention is “a powder of a resin composition containing at least a resin and two types of dyes, and at least one of the two types of dyes has a solubility in propylene glycol monomethyl ether acetate of 0. "04g / 100ml to 20g / 100ml of disperse dye or oil-soluble dye, powder". In other words, at least two or more kinds of dyes are added by adding one kind of dye to the above-mentioned problem in the powder of the resin composition containing at least one kind of dye selected from resin and disperse dye or oil-soluble dye. And containing at least one of these two dyes as a disperse dye or oil-soluble dye having a solubility in propylene glycol monomethyl ether acetate of 0.04 g / 100 ml to 20 g / 100 ml, It solves the above problems.

Further, the present invention is “a method for suppressing powder aggregation in a powder of a resin composition containing at least a resin and two kinds of dyes, wherein at least one kind of dye among the two kinds of dyes, The present invention relates to a method for suppressing powder aggregation, which is a disperse dye or an oil-soluble dye having a solubility in propylene glycol monomethyl ether acetate of 0.04 g / 100 ml to 20 g / 100 ml. In other words, at least two or more kinds of dyes are added by adding one kind of dye to the above-mentioned problem in the powder of the resin composition containing at least one kind of dye selected from resin and disperse dye or oil-soluble dye. And containing at least one of these two dyes as a disperse dye or oil-soluble dye having a solubility in propylene glycol monomethyl ether acetate of 0.04 g / 100 ml to 20 g / 100 ml, It solves the above problems.

Furthermore, the present invention is “a method for improving dyeability in a powder of a resin composition containing at least a resin and two kinds of dyes, wherein at least one of the two kinds of dyes is propylene. The present invention relates to a method for improving dyeability, which is a disperse dye or oil-soluble dye having a solubility in glycol monomethyl ether acetate of 0.04 g / 100 ml to 20 g / 100 ml. In other words, at least two or more dyes can be obtained by adding one or more dyes to the above-mentioned problem in the powder of the resin composition containing at least one resin selected from a resin and a disperse dye or an oil-soluble dye. And at least one of the at least two dyes is a disperse dye or oil-soluble dye having a solubility in propylene glycol monomethyl ether acetate of 0.04 g / 100 ml to 20 g / 100 ml. Thus, the above-mentioned problem is solved.

The solubility in propylene glycol monomethyl ether acetate is preferably 0.04 g / 100 ml to 15 g / 100 ml, more preferably 0.04 g / 100 ml to 10 g / 100 ml.
Further, the “powder” of the resin composition is used in the meaning including all powders having various shapes such as particles.
Note that propylene glycol monomethyl ether acetate means propylene glycol-1-monomethyl ether-2-acetate, and may be abbreviated as “PGMEA” in this specification.

When the powder of the resin composition contains two kinds of dyes, one of the dyes is a disperse dye or an oil-soluble dye having a solubility in PGMEA of 0.04 g / 100 ml to 20 g / 100 ml. One kind of dye is not particularly limited. The remaining one kind of dye may be various dyes described below, or a disperse dye or oil-soluble dye having a solubility in PGMEA of 0.04 g / 100 ml to 20 g / 100 ml.
When the resin composition powder contains three or more dyes, all the dyes may be disperse dyes or oil-soluble dyes having a solubility in PGMEA of 0.04 g / 100 ml to 20 g / 100 ml. Of these dyes, only one type may be a disperse dye or oil-soluble dye having a solubility in PGMEA of 0.04 g / 100 ml to 20 g / 100 ml. In such a case, it is preferable that more than half of the plurality of types of dyes are disperse dyes or oil-soluble dyes having a solubility in PGMEA of 0.04 g / 100 ml to 20 g / 100 ml, and the solubility in PGMEA is 0. It is more preferable that the number of dyes other than 0.04 g / 100 ml to 20 g / 100 ml other than the disperse dye or the oil-soluble dye is one.
When the powder of the resin composition contains a dye other than a disperse dye or an oil-soluble dye having a solubility in PGMEA of 0.04 g / 100 ml to 20 g / 100 ml, the solubility in PGMEA is 0.04 g / 100 ml to 20 g / For the content of 100 ml of disperse dye or oil-soluble dye and other dyes, the former total content is usually 50 to 80%, preferably 60 to 80%, and the latter total content is usually 20% to 50%, preferably 20% to 30%.
When the resin composition powder contains two or more dyes, at least one of the dyes is a sublimation dye, and the dispersion thereof has a solubility in PGMEA of 0.04 g / 100 ml to 20 g / 100 ml. A dye selected from the group of oil-soluble dyes consisting of disperse dyes, basic dyes, vat dyes, and solvent dyes, which is a dye or oil-soluble dye and at least one other dye is non-sublimable It is sometimes preferred to be a dye. At this time, the latter dye is preferably an oil-soluble dye represented by Formula (1) or Formula (2) described later.

The solubility of the dye in PGMEA was determined by adding an excessive disperse dye or oil-soluble dye solid in 100 ml of PGMEA at 25 ° C. and stirring for 1 hour, and then removing the solid that did not dissolve into Nutsche (filter diameter 70 mm) and filter paper (Advantech). No. 5C, 70 mm), suction bottle, and aspirator (Azuwan Corporation, ASPIRATOR model number AS-01, ultimate vacuum 0.09 MPa (25 ° C.)) are filtered under reduced pressure, and the mass of the filtration residue is measured. The measurement is performed at least twice for one dye, and the value obtained by rounding the second significant digit of the obtained numerical value is taken as the solubility of the dye. When there is a difference between the two measurement values, the numerical values obtained by the two measurements are described as the lower limit value and the upper limit value.
A person skilled in the art can easily measure the solubility in PGMEA. As an example of such a dye, three primary colors of yellow, magenta, and cyan are listed as C.I. I. Disperse Yellow 54, C.I. I. Disperse thread 60, C.I. I. Disperse Blue 359 is exemplified as a disperse dye or an oil-soluble dye having a solubility in PGMEA of 0.04 g / 100 ml to 20 g / 100 ml.

Among the two types of dyes contained in the powder of the resin composition, the type of dye other than the disperse dye or the oil-soluble dye having a solubility in PGMEA of 0.04 g / 100 ml to 20 g / 100 ml is not particularly limited. For example, water-insoluble dyes including water-soluble dyes such as reactive dyes, direct dyes, acid dyes, metal complex hydrochloric acid dyes or acid mordant dyes; and oil-soluble dyes such as disperse dyes, basic dyes, vat dyes and solvent dyes Dyes; and the like. Among these, water-insoluble dyes including oil-soluble dyes such as disperse dyes, basic dyes, and vat dyes are preferable, and water-insoluble dyes including oil-soluble dyes such as disperse dyes and basic dyes are more preferable.
In the present specification, the “water-insoluble dye” means a dye that is insoluble or hardly soluble in water. “Slightly soluble” in water means a dye having a solubility in water at 25 ° C. of usually 0.01 g / liter or less, preferably 0.001 g / liter or less.

Specific examples of reactive dyes include C.I. I. Yellow dyes such as Reactive Yellow 2, 3, 18, 81, 84, 85, 95, 99, 102; I. Orange dyes such as Reactive Orange 5, 9, 12, 13, 35, 45, 99; I. Brown dyes such as Reactive Brown 2, 8, 9, 17, 33; I. Red dyes such as Reactive Red 3, 3: 1, 4, 13, 24, 29, 31, 33, 125, 151, 206, 218, 226, 245; I. Violet dyes such as Reactive Violet 1, 24; I. Blue dyes such as Reactive Blue 2, 5, 10, 13, 14, 15, 15: 1, 49, 63, 71, 72, 75, 162, 176; I. Green dyes such as Reactive Green 5, 8, 19; I. And black dyes such as Reactive Black 1, 8, 23, 39; and the like.

Specific examples of direct dyes include C.I. I. Yellow dyes such as direct yellow 4, 5, 11, 12, 50, 86, 87, 127, 130, 132, 142, 147, 153; I. Orange dyes such as direct orange 15, 34, 39, 102; I. Brown dyes such as Direct Brown 195, 209, 210; I. Red dyes such as Direct Red 81, 89, 224, 225, 226, 227, 239, 243, 252, 255; I. Violet dyes such as direct violet 9, 51, 66; I. Blue dyes such as Direct Blue 86, 87, 108, 199, 200, 202, 218, 237, 248, 267, 273, 279, 281; I. Green dyes such as direct green 59 and 80; I. And black dyes such as direct black 19, 22, 112, 117, 161, 170, and 171;

Specific examples of acid dyes include C.I. I. Acid Yellow 1, 3, 11, 17, 18, 19, 23, 25, 36, 38, 40, 40: 1, 42, 44, 49, 59, 59: 1, 61, 65, 72, 73, 79, Yellow dyes such as 99, 104, 110, 159, 169, 176, 184, 193, 200, 204, 207, 215, 219, 219: 1, 220, 230, 232, 235, 241, 242, 246; I. Acid Orange 3, 7, 8, 10, 19, 24, 51, 56, 67, 74, 80, 86, 87, 88, 89, 94, 95, 107, 108, 116, 122, 127, 140, 142, Orange dyes such as 144, 149, 152, 156, 162, 166, 168; I. Brown dyes such as Acid Brown 2, 4, 13, 14, 19, 28, 44, 123, 224, 226, 227, 248, 282, 283, 289, 294, 297, 298, 301, 355, 357, 413; C. I. Acid Red 1, 6, 8, 9, 13, 18, 27, 35, 37, 52, 54, 57, 73, 82, 88, 97, 97: 1, 106, 111, 114, 118, 119, 127, 131, 138, 143, 145, 151, 183, 195, 198, 211, 215, 217, 225, 226, 249, 251, 254, 256, 257, 260, 261, 265, 266, 274, 276, 277, Red dyes such as 289, 296, 299, 315, 318, 336, 337, 357, 359, 361, 362, 364, 366, 399, 407, 415; I. Violet dyes such as Acid Violet 17, 19, 21, 42, 43, 47, 48, 49, 54, 66, 78, 90, 97, 102, 109, 126; I. Acid Blue 1, 7, 9, 15, 23, 25, 40, 61: 1, 62, 72, 74, 80, 83, 90, 92, 103, 104, 112, 113, 114, 120, 127, 127: 1, 128, 129, 138, 140, 142, 156, 158, 171, 182, 185, 193, 199, 201, 203, 204, 205, 207, 209, 220, 221, 224, 225, 229, 230, Blue dyes such as 239, 249, 258, 260, 264, 277: 1, 278, 279, 280, 284, 290, 296, 298, 300, 317, 324, 333, 335, 338, 342, 350; I. Acid Green 9, 12, 16, 19, 20, 25, 27, 28, 40, 43, 56, 73, 81, 84, 104, 108, 109, etc .; I. Acid Black 1, 2, 3, 24, 24: 1, 26, 31, 50, 52, 52: 1, 58, 60, 63, 107, 109, 112, 119, 132, 140, 155, 172, 187, Black dyes such as 188, 194, 207, and 222;

Specific examples of metal complex hydrochloric acid dyes include C.I. I. Acid yellow 59, 111, 112, 116, 161 and the like yellow dyes; C.I. I. Orange dyes such as Acid Orange 82, 87, 88, 95, 122, 147; I. Red dyes such as Acid Red 209, 211, 215, 216, 217, 256, 262, 317, and 355; I. Violet dyes such as Acid Violet 66, 75 and 116; I. Acid blue 167, 168, 171, 234, 250, 276 and the like; I. Brown dyes such as Acid Brown 30, 44, 45, 46, 224, 282, 283, 294, 295, 296, 297, 333, 352, 353, 369, 368; I. Acid Green 43, 60, 76, 77, 80 and other green dyes; C.I. I. Acid black 52: 1, 107, 110, 132, 155, 179 and the like black dyes;

Specific examples of acid mordant dyes include C.I. I. Mordant Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 50, 56, 61, 62, 65, etc. yellow dyes; C.I. I. Orange dyes such as mordanto orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48 C. I. Moldand Red 1, 2, 3, 4, 9, 11, 12, 14, 17, 18, 19, 22, 23, 24, 25, 26, 30, 32, 33, 36, 37, 38, 39, 41 Red dyes such as C., 43, 45, 46, 48, 53, 56, 63, 71, 74, 85, 86, 88, 90, 94, 95; I. Violet dyes such as mold violet 2, 4, 5, 7, 14, 22, 24, 30, 31, 32, 37, 40, 41, 44, 45, 47, 48, 53, 58; I. Moldan Blue 2, 3, 7, 8, 9, 12, 13, 15, 16, 19, 20, 21, 22, 23, 24, 26, 30, 31, 32, 39, 40, 41, 43, 44 48, 49, 53, 61, 74, 77, 83, 84, etc .; I. And green dyes such as Mordant Green 1, 3, 4, 5, 10, 15, 19, 26, 29, 33, 34, 35, 41, 43, and 53;

Specific examples of basic dyes include C.I. I. Yellow dyes such as Basic Yellow 1, 2, 11, 28, 51, 57, 87; I. Orange dyes such as Basic Orange 2, 14, 21, 24, 31; I. C. Brown Brown 1, 16, 17, etc. brown dyes; I. Red dyes such as Basic Red 1, 2, 5, 9, 12, 13, 14, 15, 18, 22, 27, 29, 35, 36, 40, 51, 76, 118; I. Violet dyes such as Basic Violet 1, 2, 3, 4, 7, 10, 14, 15, 20, 27; I. Blue dyes such as Basic Blue 1, 3, 5, 7, 9, 16, 22, 24, 25, 26, 28, 29, 64, 99, 117; I. Basic Green 1, 4, 5, etc. green dyes; C.I. I. Black dyes such as Basic Black 2;

Specific examples of vat dyes include C.I. I. Vat yellow 2, 4, 10, 20, 33, etc. yellow dyes; I. Vat orange 1, 2, 3, 5, 7, 9, 13, 15 etc. orange dyes; I. Vat red 1, 2, 10, 13, 15, 16, 41, 61 etc. red dye; I. Violet dyes such as vat violet 1, 2, 9, 13, 21; I. Vat blue 1, 3, 4, 5, 6, 8, 12, 14, 18, 19, 20, 29, 35, 41, etc .; I. Vat green 1, 2, 3, 4, 8, 9 etc. green dyes; C.I. I. Vat Brown 1, 3, 25, 44, 46, etc. Brown dyes; I. Bat black 1, 8, 9, 13, 14, 20, 25, 27, 29, 36, 56, 57, 59, 60, etc.

Specific examples of disperse dyes include C.I. I. Disperse Yellow 3, 4, 5, 7, 8, 9, 13, 23, 24, 30, 33, 34, 39, 42, 44, 49, 50, 51, 54, 56, 58, 60, 63, 64 , 66, 68, 71, 74, 76, 79, 82, 83, 85, 86, 88, 90, 91, 93, 98, 99, 100, 104, 114, 116, 118, 119, 122, 124, 126 135, 140, 141, 149, 160, 162, 163, 164, 165, 179, 180, 182, 183, 186, 192, 198, 199, 200, 202, 204, 210, 211, 215, 216, 218 Yellow dyes such as 224, 237; I. Disperse Orange 1, 1: 1, 3, 5, 7, 11, 13, 17, 20, 21, 23, 25, 25: 1, 29, 30, 31, 32, 33, 37, 38, 42, 43 44, 45, 47, 48, 49, 50, 53, 54, 55, 56, 57, 58, 59, 61, 66, 71, 73, 76, 78, 80, 86, 89, 90, 91, 93 Orange dyes such as C., 96, 97, 118, 119, 127, 130, 139, 142; I. Disperse thread 1, 4, 5, 7, 11, 12, 13, 15, 17, 27, 43, 44, 50, 52, 53, 54, 55, 55: 1, 56, 58, 59, 60, 65, 70, 72, 73, 74, 75, 76, 78, 81, 82, 86, 88, 90, 91, 92, 93, 96, 103, 105, 106, 107, 108, 110, 111, 113, 117, 118, 121, 122, 126, 127, 128, 131, 132, 134, 135, 137, 143, 145, 146, 151, 152, 153, 154, 157, 158, 159, 164, 167, 169, 177, 179, 181, 183, 184, 185, 188, 189, 190, 190: 1, 191, 192, 200, 201, 202, 203, 205, 206, 207, 210, 221, 224, 225, 227, 229, 239, 240, 257, 258, 277, 278, 279, 281, 283, 288, 298, 302, 303, 310, 311, 312, 320, 323, 324, Red dyes such as 328, 359; I. Disperse violet 1, 4, 8, 11, 17, 23, 26, 27, 28, 29, 31, 33, 35, 36, 38, 40, 43, 46, 48, 50, 51, 52, 56, 57 Violet dyes such as C., 59, 61, 63, 69, 77, 97; I. Green dyes such as disperse green 9; I. Brown dyes such as disperse brown 1, 2, 4, 9, 13, 19; I. Disperse Blue 3, 5, 7, 9, 14, 16, 19, 20, 26, 26: 1, 27, 35, 43, 44, 54, 55, 56, 58, 60, 60: 1, 62, 64 64: 1, 71, 72, 72: 1, 73, 73: 1, 75, 77, 79, 79: 1, 81, 81: 1, 82, 83, 87, 91, 93, 94, 95, 64 : 1, 96, 102, 106, 108, 112, 113, 115, 118, 120, 122, 125, 128, 130, 131, 139, 141, 142, 143, 145, 146, 148, 149, 153, 154 158, 165, 165: 1, 165: 2, 167, 171, 173, 174, 176, 181, 183, 185, 186, 187, 189, 197, 198, 200, 201, 205, 207, 211 214, 224, 225, 257, 259, 266, 267, 270, 281, 284, 285, 287, 288, 291, 293, 295, 297, 301, 315, 330, 333, 334, 341, 353, 354, Blue dyes such as 358, 359, 360, 364, 365, 368; I. Examples thereof include black dyes such as Disperse Black 1, 3, 10, 24.

Specific examples of solvent dyes include C.I. I. Yellow dyes such as Solvent Yellow 9, 17, 19, 21, 24, 31, 35, 43, 44, 58, 61, 80, 93, 100, 102, 103, 105, 112, 114, 162, 163; I. Orange dyes such as Solvent Orange 1, 67; I. Red dyes such as Solvent Red 1, 3, 8, 23, 24, 25, 27, 30, 49, 81, 82, 83, 84, 100, 109, 121, 146; I. Violet dyes such as Solvent Violet 8, 21; I. Blue dyes such as Solvent Blue 2, 11, 25, 36, 55, 63, 83, 105, 111; I. Green dyes such as Solvent Green 3; I. Brown dyes such as Solvent Brown 3; C.I. I. And black dyes such as Solvent Black 3, 5, 7, 22, 27, 29, and the like.

The above dyes are, for example, anthraquinone, azo, azomethine, indophenol, indoaniline, quinophthalone, methine, anthrapyridone, naphthalimide, xanthene, triallylmethane, quinacridone, The compounds can be classified into oxazine-based, pyrroline-based, cyanine-based, and phthalocyanine-based compounds.
Among the dyes contained in the powder of the resin composition, at least one kind of dye may be any dye as long as it is a disperse dye or an oil-soluble dye having a solubility in PGMEA of 0.04 g / 100 ml to 20 g / 100 ml. Can be used together.
Among them, anthraquinone and anthraquinone, anthraquinone and azo, anthraquinone and azomethine, anthraquinone and indophenol, anthraquinone and indoaniline, anthraquinone and pyrroline, quinophthalone and quinophthalone, quinophthalone And anthraquinone, quinophthalone and azo, quinophthalone and naphthalimide, azo and azo, azo and azomethine, azo and indophenol, azo and indoaniline, azo and pyrroline, etc. It is preferable to contain 2 or more types of dyes including the combination of these compounds.
Among these combinations, it is more preferable to contain two or more kinds of dyes including combinations of anthraquinone and anthraquinone, anthraquinone and azo, quinophthalone and azo, and quinophthalone and anthraquinone. .

Any of the above dyes may be used alone. Further, two or more types may be used (mixed) in accordance with the purpose of obtaining a desired color tone.
For example, in the preparation of a black ink, a blue dye as a main component, an orange dye and a red dye can be appropriately blended to adjust a black color, and this can be used as a black dye. Further, for example, a plurality of dyes may be blended for the purpose of finely adjusting a color tone such as blue, orange, red, violet, or black to a desired color tone.
However, even when a plurality of dyes are used in combination, at least one of the dyes contained in the powder of the resin composition has a solubility in PGMEA of 0.04 g / 100 ml to 20 g / 100 ml of disperse dye or oil-soluble dye.

Among the above dyes, there is a difference in the easiness of the resin composition to come out on the surface, and disperse dyes and oil-soluble dyes tend to come out on the surface, and as a result, powder aggregation tends to occur. Further, among disperse dyes and oil-soluble dyes, dyes having sublimation properties are more likely to appear on the surface of the resin composition. For this reason, the inhibitory effect of powder aggregation is exhibited very well in the powder of the resin composition containing these dyes.

There is no restriction | limiting in particular as resin which the powder of the said resin composition contains, If it can mix with dye, it can select suitably according to a use purpose from well-known resin.
Specific examples thereof include, for example, a polymer of styrene or a styrene derivative, a styrene copolymer, polymethyl methacrylate, polybutyl methacrylate, polyvinyl chloride, polyvinyl acetate, polyethylene, polypropylene, polyester, epoxy resin, epoxy polyol resin. , Polyurethane, polyamide, polyvinyl butyral, polyacrylic acid resin, rosin, modified rosin, terpene resin, aliphatic hydrocarbon resin, alicyclic hydrocarbon resin, aromatic petroleum resin, chlorinated paraffin, paraffin wax, etc. .
Any of the above-described resins may be used alone or in combination of two or more.

Examples of the styrene or styrene derivative polymer include polystyrene, poly p-chlorostyrene, and polyvinyltoluene.
Examples of the styrene copolymer include a styrene-p-chlorostyrene copolymer, a styrene-propylene copolymer, a styrene-vinyltoluene copolymer, a styrene-vinylnaphthalene copolymer, and a styrene-acrylic acid ester copolymer. Polymers (styrene-methyl acrylate copolymer, styrene-ethyl acrylate copolymer, styrene-butyl acrylate copolymer, styrene-octyl acrylate copolymer, etc.), styrene-methacrylic acid ester copolymer ( Styrene-methyl methacrylate copolymer, styrene-ethyl methacrylate copolymer, styrene-butyl methacrylate copolymer, etc.), styrene-α-chloromethyl methacrylate copolymer, styrene-acrylonitrile copolymer, styrene- Vinyl methyl ketone copolymer, styrene-butadiene Polymers, styrene - isoprene copolymer, styrene - acrylonitrile - indene copolymer, styrene - maleic acid copolymer, styrene - maleic acid ester copolymers and the like.

As an example of a commercial product of the above-mentioned resin, it is known as a styrene-acrylic acid ester copolymer, such as Diacron FC-684, Diacron FC-1224, Diacron FC-316 made by Mitsubishi Rayon Co., Ltd. known as polyester CPR-100, CPR-250, CPR-390, etc. manufactured by Mitsui Chemicals, Inc.

The use of the resin composition powder is not particularly limited. For example, a coloring material contained in a printing ink or liquid toner such as an ultraviolet curable ink, a thermosetting ink, an inkjet ink, a gravure ink, or an offset ink; Examples include silver halide photosensitive materials; thermal transfer recording materials; coloring materials containing recording pens, optical recording medium materials, adhesives, etc .; coloring materials containing powder paints, powder toners, etc. . Among these uses, as coloring materials contained in printing inks and liquid toners such as ultraviolet curable inks, thermosetting inks, inkjet inks, gravure inks and offset inks; powder paints, powder toners, etc. Are preferable, and examples thereof include powdered colored resin compositions, powder paints, and powder toners contained in liquid toners.

There is no restriction | limiting in particular in the total content of the dye which the powder of the said resin composition contains, According to the objective, it can select suitably. The standard is usually 1 to 40%, preferably 2 to 35%, more preferably 3 to 25% with respect to the total mass of the powder.
When the total content of the dye is less than 1%, sufficient performance as a coloring material cannot be exhibited, and when it exceeds 40%, the dye is not melted or dispersed in the powder, and it is difficult to suppress powder aggregation. In addition, it becomes difficult to improve the dyeability.

The powder of the resin composition can be used for various applications as described above. For this reason, the powder of this resin composition may contain additives other than resin according to the use application.
As an example of the additive, powder toner may be mentioned, for example, additives such as wax, charge control agent, and external additive. These types, the content of the resin composition in the total mass of the powder, and the production method of the powder toner containing these additives are all described in known prior art documents. When the powder of the resin composition is used as a powder toner, it may be prepared as a powder toner based on known prior art documents, and may be prepared in the same manner when used for other purposes.
Even if the powder of the said resin composition contains such an additive, the sufficient aggregation inhibitory effect is exhibited.

Of the above, a combination of preferable ones is more preferable, and a combination of more preferable ones is more preferable. The same applies to combinations of preferable and more preferable, combinations of more preferable, and more preferable.

The method for suppressing powder agglomeration of the present invention can suppress a phenomenon in which a dye appears on the surface of a powder of a resin composition, particularly during transportation, use or storage at a high temperature. . For this reason, it is possible to suppress the powder aggregation of the resin composition, and it is possible to provide a high-quality resin composition powder that has extremely high heat stability and stability over time and can be applied to various applications.
In addition, the dyeing property improving method of the present invention suppresses the phenomenon that the dye appears on the surface of the powder of the resin composition, particularly during transportation at high temperature, use, or storage. It improves various dyeing properties. These various dyeing properties include sweeping unevenness, image memory, dyeing density, white background contamination, dyeing unevenness, dyeing reproducibility, build-up property, dyeing property, leveling property and the like. Thus, the present invention can provide a method for improving dyeability using a resin composition powder, which has extremely high heat stability and stability over time and can be applied to various applications.

The present invention will be described in more detail with reference to the following examples, but the present invention is not limited to these examples.
In the examples, the average particle size was measured using a precision particle size distribution measuring device “Multisizer 3 (manufactured by Beckman Coulter, Inc.)”.

<Example A>
As an example of the powder of the resin composition, a powder toner was prepared, and the effect of suppressing the aggregation was tested.
[Example A-1]
(Process 1)
Mitsubishi Rayon Co., Ltd. Diacron FC-316 (105 parts), Kayaset Yellow AG (Nippon Kayaku Co., Ltd., CI Disperse Yellow 54: 5 parts), represented by the following formula (1) Dye (5 parts), Bontron E-84 (1 part) and Carnauba wax C1 (4 parts) were placed in a Henschel mixer, premixed for 10 minutes at a rotational speed of 30 m / sec, and then melted by a twin screw extruder. Kneaded. The obtained melt-kneaded product was pulverized and classified using a pulverizer / classifier to obtain toner base particles having an average particle diameter of 7.8 μm.
The dye represented by the following formula (1) was synthesized by the method described in JP-A-6-184481.

(Process 2)
Toner base particles (100 parts) obtained in Example A-1 (Step 1), H05TM (1.5 parts) manufactured by Clariant Japan, TG-811F (1.5 parts) manufactured by Cabot, Titanium Industry SW-100 (1.0 part) manufactured by KK was placed in a Henschel mixer and stirred at a rotational speed of 30 m / sec for 10 minutes to prepare a yellow toner.

[Example A-2]
(Process 1)
Mitsubishi Rayon Co., Ltd. Diacron FC-316 (96 parts), C.I. I. Disperse Blue 359 (11.5 parts), a dye represented by the following formula (2) (3 parts), Bontron E-84 (1 part), and Carnauba wax C1 (4 parts) were placed in a Henschel mixer, 30 m / After premixing for 10 minutes at a rotational speed of seconds, the mixture was melt-kneaded by a twin screw extruder. The obtained melt-kneaded product was pulverized and classified using a pulverizer / classifier to obtain toner base particles having an average particle diameter of 7.5 μm.
The dye represented by the following formula (2) was synthesized by the method described in JP-A-6-228444.

(Process 2)
Toner base particles (100 parts) obtained in Example A-2 (Step 1), H05TM (1.5 parts) manufactured by Clariant Japan, TG-811F (1.5 parts) manufactured by Cabot, Titanium Industry SW-100 (1.0 part) manufactured by KK was put in a Henschel mixer and stirred at a rotational speed of 30 m / sec for 10 minutes to prepare a cyan toner.

[Comparative Example A-3]
(Process 1)
Mitsubishi Rayon Co., Ltd. Diacron FC-316 (105 parts), Kayaset Yellow AG (Nippon Kayaku Co., Ltd., CI Disperse Yellow 54: 5 parts), Bontron E-84 (1 part) ), Carnauba wax C1 (4 parts) was placed in a Henschel mixer, premixed for 10 minutes at a rotational speed of 30 m / sec, and then melt-kneaded by a twin screw extruder. The obtained melt-kneaded product was pulverized and classified using a pulverizer / classifier to obtain toner base particles having an average particle diameter of 7.8 μm.

(Process 2)
Toner base particles (100 parts) obtained in Comparative Example A-3 (Step 1), H05TM (1.5 parts) manufactured by Clariant Japan, TG-811F (1.5 parts) manufactured by Cabot, Titanium Industry SW-100 (1.0 part) manufactured by KK was placed in a Henschel mixer and stirred at a rotational speed of 30 m / sec for 10 minutes to obtain a comparative yellow toner containing only one type of dye.

[Comparative Example A-4]
(Process 1)
Mitsubishi Rayon Co., Ltd. Diacron FC-316 (96 parts), Nippon Kayaku Co., Ltd. C.I. I. Disperse Blue 359 (11.5 parts), Bontron E-84 (1 part) and Carnauba wax C1 (4 parts) were placed in a Henschel mixer and premixed for 10 minutes at a rotational speed of 30 m / second, followed by twin-screw extrusion. It was melt kneaded with a machine. The obtained melt-kneaded product was pulverized and classified using a pulverizer / classifier to obtain toner base particles having an average particle diameter of 7.8 μm.

(Process 2)
Toner base particles (100 parts) obtained in Comparative Example A-4 (Step 1), H05TM (1.5 parts) manufactured by Clariant Japan, TG-811F (1.5 parts) manufactured by Cabot, Titanium Industry SW-100 (1.0 part) manufactured by KK was put in a Henschel mixer and stirred at a rotational speed of 30 m / sec for 10 minutes to obtain a comparative cyan toner containing only one type of dye.

The solubility of each dye contained in the powder of each resin composition prepared as described above in PGMEA is shown in Table 1 below.
The abbreviations in Table 1 below have the following meanings.
DsY 54: C.I. I. Disperse Yellow 54.
DsB 359: C.I. I. Disperse Blue 359.

The aggregation property of each powder toner prepared as described above was evaluated based on the following method. The results are shown in Table 2.

[Cohesiveness evaluation test]
Weigh 5.0 g of toner in a 50 ml glass tube (manufactured by Nidec Rika Glass Co., Ltd., SV-50A), seal with a cap lid, store for 24 hours under the following four conditions, and then leave it to return to room temperature. did. Thereafter, the cap lid was opened and the glass tube bottle was turned upside down, and the discharge state of each powder toner and the presence or absence of powder agglomerates were evaluated according to the following evaluation criteria AC.
Condition 1: Stored at room temperature (25 ° C.) for 24 hours.
Condition 2: Place in a thermostat at 40 ° C ± 1 ° C and store for 24 hours.
Condition 3: Place in a thermostat at 50 ° C. ± 1 ° C. and store for 24 hours.
Condition 4: Place in a thermostat at 60 ° C. ± 1 ° C. and store for 24 hours.

[Aggregation evaluation criteria]
A: Immediately after turning upside down, the toner inside is discharged by natural fall.
B: Even if it is turned upside down, it will not be discharged immediately, but it will naturally fall within 30 seconds to 1 minute.
C: Even if it passes upside down for more than 1 minute, it does not fall naturally.
The more the powder is agglomerated, the more difficult it is to spontaneously fall. Therefore, the shorter the time to natural fall means that powder agglomeration does not occur, which is an excellent state.

[Presence of agglomerates]
A: Agglomerates are not found in the powder that spontaneously falls.
B: Although the powder which fell spontaneously is in the shape of a lump, it returns to powder as soon as it is pressed with a finger.
C: The fallen powder has agglomerates and does not return to powder even when pressed with a finger.
It means that the powder is in such an excellent state that no agglomerates are formed.

As apparent from Table 2, the powder toner of the present invention has reduced powder agglomeration from both aspects of agglomeration and agglomerate formation, and it is clear that the powder toner has an effect of suppressing powder agglomeration. became.

Hereinafter, preparation examples of the resin composition powder will be described as Examples A-5 to A-12 and Comparative Examples A-13 to A-16, respectively. The mixer used in each preparation example is BM-RS08 manufactured by ZOJIRUSHI CORP.

[Example A-5]
Mitsubishi Rayon Co., Ltd. Diacron FC-316 (50.0 parts), Kayaset Yellow AG (Nippon Kayaku Co., Ltd., CI Disperse Yellow 54: 2.4 parts), the above formula ( The dye represented by 1) (2.4 parts) was melt blended on a hot plate heated to 220 ° C. After cooling, the resulting kneaded product was pulverized with a mixer to obtain a resin composition powder.

[Example A-6]
Mitsubishi Rayon Co., Ltd. Diacron FC-316 (36.0 parts), Nippon Kayaku Co., Ltd. C.I. I. Disperse Blue 359 (2.5 parts) and the dye represented by the above formula (2) (1.5 parts) were melt-blended on a hot plate heated to 220 ° C. After cooling, the resulting kneaded product was pulverized with a mixer to obtain a resin composition powder.

[Example A-7]
Mitsubishi Rayon Co., Ltd. Diacron FC-316 (52.5 parts), C.I. I. Disper Thread 60 (Nippon Kayaku Co., Ltd .: 3.0 parts), C.I. I. Disperse thread 92 (manufactured by Nippon Kayaku Co., Ltd .: 2.0 parts) was melt blended on a hot plate heated to 220 ° C. After cooling, the resulting kneaded product was pulverized with a mixer to obtain a resin composition powder.

[Example A-8]
Mitsubishi Rayon Co., Ltd. Diacron FC-316 (52.5 parts), C.I. I. Disper Thread 60 (Nippon Kayaku Co., Ltd .: 3.0 parts), C.I. I. Disperse thread 74 (Nippon Kayaku Co., Ltd .: 2.0 parts) was melt blended on a hot plate heated to 220 ° C. After cooling, the resulting kneaded product was pulverized with a mixer to obtain a resin composition powder.

[Example A-9]
Mitsubishi Rayon Co., Ltd. Diacron FC-316 (52.5 parts), C.I. I. Disperse Blue 359 (Nippon Kayaku Co., Ltd .: 2.5 parts) and the dye represented by the above formula (1) (2.5 parts) were melt blended on a hot plate heated to 220 ° C. After cooling, the resulting kneaded product was pulverized with a mixer to obtain a resin composition powder.

[Example A-10]
Mitsubishi Rayon Co., Ltd. Diacron FC-316 (52.0 parts), C.I. I. Disperse Blue 359 (Nippon Kayaku Co., Ltd .: 1.5 parts), Kayaset Yellow AG (Nippon Kayaku Co., Ltd., CI Disperse Yellow 54: 2.0 parts), the above formula ( The dye represented by 1) (4.0 parts) was melt blended on a hot plate heated to 220 ° C. After cooling, the resulting kneaded product was pulverized with a mixer to obtain a resin composition powder.

[Example A-11]
Mitsubishi Rayon Co., Ltd. Diacron FC-316 (52.0 parts), Kayaset Yellow AG (Nippon Kayaku Co., Ltd., CI Disperse Yellow 54: 2.0 parts), formula (1 ) And a dye represented by the formula (2) (1.5 parts) were melt blended on a hot plate heated to 220 ° C. After cooling, the resulting kneaded product was pulverized with a mixer to obtain a resin composition powder.

[Example A-12]
Mitsubishi Rayon Co., Ltd. Diacron FC-316 (45.8 parts), C.I. I. Disperse Blue 359 (Nippon Kayaku Co., Ltd .: 2.1 parts), dye represented by formula (2) (1.3 parts), C.I. I. A dye (1.5 parts) represented by Solvent Blue 63 (Nippon Kayaku Co., Ltd .: 0.9 parts) was melt blended on a hot plate heated to 220 ° C. After cooling, the resulting kneaded product was pulverized with a mixer to obtain a resin composition powder.

[Comparative Example A-13]
Mitsubishi Rayon Co., Ltd. Diacron FC-316 (52.5 parts), Kayaset Yellow AG (Nippon Kayaku Co., Ltd., CI Disperse Yellow 54: 5.0 parts) at 220 ° C Melt blended on a heated hot plate. After cooling, the obtained kneaded product was pulverized with a mixer to obtain a comparative resin composition powder.

[Comparative Example A-14]
Mitsubishi Rayon Co., Ltd. Diacron FC-316 (48.0 parts), Nippon Kayaku Co., Ltd. C.I. I. Disperse Blue 359 (6.5 parts) was melt blended on a hot plate heated to 220 ° C. After cooling, the obtained kneaded product was pulverized with a mixer to obtain a comparative resin composition powder.

[Comparative Example A-15]
Mitsubishi Rayon Co., Ltd. Diacron FC-316 (52.5 parts), Kayaset Yellow AH (Nippon Kayaku Co., Ltd., CI Disperse Yellow 160: 2.5 parts), the above formula ( The dye represented by 1) (2.5 parts) was melt blended on a hot plate heated to 220 ° C. After cooling, the obtained kneaded product was pulverized with a mixer to obtain a comparative resin composition powder.

[Comparative Example A-16]
Mitsubishi Rayon Co., Ltd. Diacron FC-316 (52.5 parts), Kayaset Yellow AH (Nippon Kayaku Co., Ltd., CI Disperse Yellow 160: 2.5 parts), the above formula ( The dye represented by 2) (2.5 parts) was melt blended on a hot plate heated to 220 ° C. After cooling, the obtained kneaded product was pulverized with a mixer to obtain a comparative resin composition powder.

The solubility of each dye contained in the powder of each resin composition prepared as described above in PGMEA is shown in Table 3 below. In Table 3 below, “<0.01” means that the solubility in PGMEA is less than 0.01 g / 100 ml.
The abbreviations in Table 3 below have the following meanings.
DsY54: C.I. I. Disperse Yellow 54.
DsY160: C.I. I. Disperse Yellow 160.
DsR60: C.I. I. Disperse thread 60.
DsR74: C.I. I. Disperse thread 74.
DsR92: C.I. I. Disperse thread 92.
DsB359: C.I. I. Disperse Blue 359.
SvB63: C.I. I. Solvent Blue 63.

The bleedability of the powder of each resin composition prepared as described above was evaluated based on the following method. The results are shown in Table 4 below.

[Bleedability test]
Weigh 5.0 g of the dye resin composition in a 50 ml glass tube (manufactured by Nidec Rika Glass Co., Ltd., SV-50A), seal it with a cap lid, store it under the following two conditions, and leave it still until it returns to room temperature. I put it. Thereafter, the presence or absence of bleed-out was evaluated according to the following evaluation criteria A to D from photographs of the electron microscope (S-4800 field emission scanning electron microscope manufactured by Hitachi High-Technologies Corporation) of the powder of each resin composition. .
Condition 1: Stored at room temperature (25 ° C.) for 24 hours.
Condition 2: Place in a thermostat at 60 ° C. ± 1 ° C. and store for 24 hours.

[Evaluation criteria]
A: The bleed-out solid is hardly observed.
B: A bleed-out solid is observed, but most of the solids are less than 1 μm.
C: A bleed-out solid is observed, but many medium-sized solids of 1 μm or more and less than 3 μm are observed.
D: There are many solids that bleed out, and many large solids of 3 μm or more are observed.

As is apparent from Table 4, the powder of the present invention was found to have an effect of suppressing bleed out at high temperatures. Further, as the evaluation result of bleed-out deteriorated from A to D, the cohesiveness and the state of the coagulated mass also deteriorated, and it was confirmed that there is a correlation between the bleed-out and the cohesiveness.

<Example B>
As an example of the powder of the resin composition, a powder toner was prepared, and the effect of improving the dyeability was tested.

[Example B-1]
A yellow toner of Example B-1 was prepared in the same manner as in Example A-1 (Step 1) and (Step 2). The yellow toners of Example A-1 and Example B-1 are substantially the same toner.

[Example B-2]
A cyan toner of Example B-2 was prepared in the same manner as in Example A-2 (Step 1) and (Step 2). The cyan toners of Example A-2 and Example B-1 are substantially the same toner.

[Comparative Example B-3]
A yellow toner of Comparative Example B-3 was prepared in the same manner as Comparative Example A-3 (Step 1) and (Step 2). The yellow toners of Comparative Example A-3 and Comparative Example B-3 are substantially the same toner.

[Comparative Example B-4]
In the same manner as in Comparative Example A-4 (Step 1) and (Step 2), a yellow toner of Comparative Example B-4 was prepared. The yellow toners of Comparative Example A-4 and Comparative Example B-4 are substantially the same toner.

The solubility of each dye contained in the powder of each resin composition prepared as described above in PGMEA is as shown in Table 1 above.

Using the toners of the above examples and comparative examples, the dyeability was evaluated by the following method. The evaluation results are shown in Table 5.

Each color toner obtained in the above Examples and Comparative Examples was filled in a dry non-magnetic one-component developing type printer (Katsukawa Electric Co., Ltd .: KIPc7800). Using an A0 size bond paper as an intermediate recording medium, an intermediate recording medium (bond paper) on which a solid image was printed under the conditions of resolution: 600 pixels / inch, fixing temperature: 140 ° C., development bias: 200 V was obtained.

Evaluation test 1: [Image quality of intermediate recording medium]
Each of the obtained intermediate recording media was visually observed for sweeping unevenness and presence of an image memory, and image quality was evaluated according to the following evaluation criteria. The evaluation results are shown in Table 5 below.

A: A uniform solid image is obtained without unevenness in sweeping and image memory.
B: Sweep unevenness and image memory are slightly observed.
C: Uneven sweeping and image memory are clearly observed.
D: Extremely conspicuous sweep unevenness and image memory are clearly observed.

After superposing the toner adhering surface of each obtained intermediate recording medium on a double picket (weight per unit area: 90 g / m ² ) made of 100% polyester fiber as the object to be dyed, a heat press machine (manufactured by Taiyo Seiki Co., Ltd.) By using a transfer press machine TP-600A2), heat treatment was performed under the conditions of 195 ° C. × 60 seconds to obtain dyed double pickets dyed by the sublimation transfer dyeing method.

Evaluation test 2: [Dyeing density]
The dyed portion of each dyed product thus obtained was measured using a spectrophotometer “Spectroeye (manufactured by Gretag Macbeth)” to measure the dyeing density. A staining density of 1.35 or higher indicates that it is good. In each of the examples and comparative examples, the staining density was 1.4 or more, and the staining density was good.

Evaluation Test 3: [Evaluation by Colorimetry of White Contamination of Dyeing]
The white background portion of each dyed product obtained in Evaluation Example 1 is measured using a spectrophotometer “Spectroeye (manufactured by Gretag Macbeth)”, and the following degree of white background contamination (= measurement of the white background portion of each dyed product) Value—a value obtained by measuring the color of a double picket before dyeing in the same manner). The evaluation results are shown in Table 5 below.

Evaluation Test 4: [Visual Evaluation of Dyeing Contamination on White Background]
In each dyed product used in Evaluation Example 2, the degree of contamination of the white portion where the color measurement was performed was visually observed and evaluated according to the following four-stage criteria. The evaluation results are shown in Table 5 below.

A: Almost no white background contamination is observed.
B: White background contamination is slightly observed.
C: It is clearly observed that the white background is contaminated.
D: It is clearly observed that the white background is heavily contaminated.

Evaluation test 5: [Evaluation by visual inspection of dyeing unevenness of dyed product]
In each dyed product used in Evaluation Example 4, the degree of uneven dyeing was visually observed and evaluated according to the following four-stage criteria. The evaluation results are shown in Table 5 below.

A: A high-quality dyed product having no dyeing unevenness is obtained.
B: Dyeing unevenness is slightly observed.
C: Dyeing unevenness is clearly observed.
D: It is clearly observed that there is intense dyeing unevenness.

As is clear from Table 5, it was found that each example improved all dyeing properties to the same or better level as compared with each comparative example.

The method for suppressing powder aggregation of the present invention is extremely useful because it can suppress aggregation of powder of a resin composition containing a dye that can be used in various applications. In addition, the dyeing property improving method of the present invention has a high dyeing concentration, and can suppress white background contamination and dyeing unevenness of the dyed product, so that it is used for direct dyeing by electrophotography, sublimation transfer dyeing, etc. It is extremely useful as a method for obtaining a high-quality dyed product or printed matter free from image defects in dyeing or printing using a powder toner or powder coating material containing the toner.

Claims

A powder of a resin composition containing at least a resin and two types of dyes, wherein at least one of the two types of dyes has a solubility in propylene glycol monomethyl ether acetate of 0.04 g / 100 ml to 20 g. / 100 ml of disperse dye or oil-soluble dye.
Of the at least two kinds of dyes, the at least one dye is a disperse dye or oil-soluble dye having a solubility in propylene glycol monomethyl ether acetate of 0.04 g / 100 ml to 20 g / 100 ml. The powder according to claim 1, wherein the dye is a dye selected from the group of oil-soluble dyes consisting of disperse dyes, basic dyes, vat dyes, and solvent dyes.
Among the at least two kinds of dyes, the at least one kind of dye is a dye selected from anthraquinone series, quinophthalone series, and azo series compounds,
The at least one other dye is an anthraquinone, azo, azomethine, indophenol, indoaniline, pyrroline, quinophthalone, naphthalimide compound, disperse dye, basic dye, The powder according to claim 1 or 2, which is a dye selected from the group of oil-soluble dyes comprising vat dyes and solvent dyes.
The powder according to any one of claims 1 to 3, wherein the at least one other dye is a dye selected from the group of oil-soluble dyes consisting of disperse dyes, basic dyes, and solvent dyes.
The resin composition powder according to any one of claims 1 to 4, which is used for suppressing powder aggregation or used as a colorant in a method for improving dyeability.
A toner containing the powder of the resin composition according to any one of claims 1 to 4, at least a charge control agent, a wax, and an external additive.
The toner according to claim 6, which is used for suppressing powder aggregation or used as a colorant in a method for improving dyeability.
A method for suppressing powder aggregation in the powder of the resin composition according to any one of claims 1 to 4.
A method for improving dyeability in a dyeing method using the powder of the resin composition according to any one of claims 1 to 4 as a colorant.
A dyeing method using the powder of the resin composition according to any one of claims 1 to 4.
A substance stained by the staining method according to claim 10.
The dyeing method using the resin composition powder as a colorant comprises attaching the resin composition powder to an intermediate recording medium by an electrophotographic method, and the resin composition powder attached to the intermediate recording medium contains The dyeing property improving method according to claim 9, which is a sublimation transfer dyeing method in which dyeing is performed by sublimation-transferring a dye to be dyed to a dyed object.
13. An intermediate recording medium according to claim 12, wherein the powder of the resin composition is adhered by an electrophotographic method.