JP6188136B2 - Method for improving dyeability - Google Patents

Description

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

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 as a colorant in various fields such as thermal transfer recording materials, recording pens, optical recording medium materials, adhesives, powder paints, and powder toners.
Examples of the dyeing method using the resin composition powder containing these dyes as a colorant include, for example, an ink-jet dyeing method using an ink-jet ink, an electrophotographic dyeing method using a dry powder toner or a liquid toner, and the like. Is mentioned.
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.
As dry powder toners and liquid toners used in the electrophotographic system, for example, various types are disclosed in Patent Documents 2 to 5.
Sublimation transfer dyeing using an electrophotographic method is disclosed, for example, in Patent Documents 6 to 10 below.

JP-A-8-34941 JP 2012-1829 A JP-A-5-27474 Japanese Patent Laid-Open No. 9-73198 Japanese Patent Laid-Open No. 3-18866 Japanese Patent Laid-Open No. 02-295787 Japanese Patent Application Laid-Open No. 06-051591 Japanese Patent Laid-Open No. 10-058638 JP 2000-029238 A JP 2006-500602 Gazette

  An object of the present invention is to provide a method for improving dyeability in a dyeing method using a powder of a resin composition containing at least a resin and two kinds of dyes as a colorant.

  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 was completed by finding that the above problems can be solved by using a disperse dye or oil-soluble dye having a solubility in acetone of 0.01 g / 100 ml to 20 g / 100 ml. That is, the present invention relates to the following (1) to (9).

(1)
A method for improving dyeability in a dyeing method using a powder of a resin composition containing at least a resin and at least two kinds of dyes as a colorant, wherein at least one of the at least two kinds of dyes A method for improving dyeability, wherein the dye is a disperse dye or an oil-soluble dye having a solubility in acetone of 0.01 g / 100 ml to 20 g / 100 ml.
(2)
Among the at least two kinds of dyes, at least one dye is a disperse dye or oil-soluble dye having a solubility in acetone of 0.01 g / 100 ml to 20 g / 100 ml, and at least one dye is a disperse dye or basic dye. The method for improving dyeability according to (1) above, which is a dye selected from the group of oil-soluble dyes consisting of dyes, vat dyes, and solvent dyes.
(3)
Among the at least two kinds of dyes, at least one dye is a disperse dye or oil-soluble dye having a solubility in acetone of 0.01 g / 100 ml to 20 g / 100 ml, and at least one dye is a disperse dye or basic dye. The method for improving dyeability according to (1) above, which is a dye selected from the group of oil-soluble dyes consisting of dyes and solvent dyes.
(4)
Of the at least two dyes, at least one dye is a disperse dye or an oil-soluble dye having a solubility in acetone of 0.01 g / 100 ml to 20 g / 100 ml, and at least one dye is represented by the following formula (1): And the method for improving dyeability according to (1) above, which is an oil-soluble dye selected from Formula (2).

(5)
A powder of a resin composition containing at least a resin and at least two types of dyes used in the method for improving dyeability described in (1) above, wherein at least one of the at least two types of dyes The resin composition powder is a disperse dye or an oil-soluble dye having a solubility in acetone of 0.01 g / 100 ml to 20 g / 100 ml.
(6)
The dyeing | staining method using the powder of the resin composition as described in said (5).
(7)
A substance stained by the staining method described in (6) above.
(8)
A dyeing method using a resin composition powder containing at least a resin and at least two kinds of dyes as a colorant is obtained by attaching the resin composition powder to an intermediate recording medium by an electrophotographic method. The dyeing property according to any one of (1) to (4) above, wherein the dye contained in the powder of the resin composition adhered to the medium is dyed by sublimation transfer to a dyed object. How to improve.
(9)
An intermediate recording medium in which the powder of the resin composition is adhered by an electrophotographic method in the method for improving dyeability described in (8) above.

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

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 method for improving dyeability in 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 solubility in acetone. Is a disperse dye or oil-soluble dye of 0.01 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 an oil-soluble dye having a solubility in acetone of 0.01 g / 100 ml to 20 g / 100 ml. It solves the problem.
The solubility in acetone is preferably 0.02 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.
When the powder of the resin composition contains two kinds of dyes, if one of the dyes is a disperse beverage or oil-soluble dye having a solubility in acetone of 0.01 g / 100 ml to 20 g / 100 ml, the rest The one kind of dye is not particularly limited. The remaining one kind of dye may be the various dyes described below, or a disperse beverage or oil-soluble dye having a solubility in acetone of 0.01 g / 100 ml to 20 g / 100 ml.
When the resin composition powder contains three or more types of dyes, all the dyes may be dispersed beverages or oil-soluble dyes having a solubility in acetone of 0.01 g / 100 ml to 20 g / 100 ml. Of these dyes, only one type may be a disperse beverage or oil-soluble dye having a solubility in acetone of 0.01 g / 100 ml to 20 g / 100 ml. In such a case, among a plurality of types of dyes, more than half of the dyes are preferably a dispersion beverage or oil-soluble dye having a solubility in acetone of 0.01 g / 100 ml to 20 g / 100 ml, and the solubility in acetone is preferably It is more preferable that there is one kind of dye other than 0.01 g / 100 ml to 20 g / 100 ml of the dispersion beverage or the oil-soluble dye.
When the resin composition contains a dye other than a disperse beverage having a solubility in acetone of 0.01 g / 100 ml to 20 g / 100 ml or an oil-soluble dye, the solubility in acetone is 0.01 g / 100 ml to 20 g / 100 ml. As for the content of the dispersion beverage or oil-soluble dye and the 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%.

The solubility of the dye in acetone was determined by adding an excessive disperse dye or oil-soluble dye solid in 100 ml of acetone at 25 ° C. and stirring for 1 hour. 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. To decide.
The measurement is performed at least twice for one dye, and the value obtained by rounding the second significant digit of the obtained 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.
Those skilled in the art can easily measure the solubility in acetone. As an example of such a dye, the three primary colors of yellow, magenta, and cyan are 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 acetone of 0.01 g / 100 ml to 20 g / 100 ml.

Of 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 acetone of 0.01 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. Black dyes such as Reactive Black 1, 8, 23, 39; and the like.

Specific examples of the direct dye 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. Direct black 19
, 22, 112, 117, 161, 170, 171 and the like;

  Specific examples of the acid dye 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 the metal complex hydrochloric acid dye include C.I. I. Yellow dyes such as Acid Yellow 59, 111, 112, 116, 161; 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, 355; I. Violet dyes such as Acid Violet 66, 75, 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. A black dye such as Acid Black 52: 1, 107, 110, 132, 155, 179;

  Specific examples of the acid mordant dye 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 the basic dye 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. Brown dyes such as Basic Brown 1, 16, 17; 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. B. Blue dyes such as Basic Blue 1, 3, 5, 7, 9, 16, 22, 24, 25, 26, 28, 29, 64, 99, 117; I. Green dyes such as Basic Green 1, 4, 5; I. Black dyes such as Basic Black 2;

  Specific examples of vat dyes include C.I. I. Yellow dyes such as vat yellow 2, 4, 10, 20, 33; I. Orange dyes such as Vat Orange 1, 2, 3, 5, 7, 9, 13, 15; I. Red dyes such as Vat Red 1, 2, 10, 13, 15, 16, 41, 61; I. Violet dyes such as vat violet 1, 2, 9, 13, 21; I. B. Blue dyes such as 1, 3, 4, 5, 6, 8, 12, 14, 18, 19, 20, 29, 35, 41; I. Green dyes such as Vat Green 1, 2, 3, 4, 8, 9; I. Brown dyes such as Vat Brown 1, 3, 25, 44, 46; I. And black dyes such as Bat Black 1, 8, 9, 13, 14, 20, 20, 25, 27, 29, 36, 56, 57, 59, 60;

  Specific examples of the disperse dye 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 the solvent dye 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.

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 acetone of 0.01 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 coming out to the surface of the resin composition, and disperse dyes and oil-soluble dyes are likely to appear 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 effect of improving dyeability is exhibited extremely 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. Polymer (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 copolymer, styrene-isoprene copolymer, styrene-acrylonitrile-indene copolymer, styrene-maleic acid copolymer, styrene-maleic acid ester A copolymer etc. are mentioned.

  As an example of a commercial product of the above resin, Diacron FC-684, Diacron FC-1224, Diacron FC-316, etc. manufactured by Mitsubishi Rayon Co., Ltd., known as polyester, etc .; known as styrene-acrylate copolymer 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. As a guide, it is usually 1 to 40%, preferably 2 to 35% 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%, it is 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 dyeing | staining property improvement effect is exhibited.

  The dyeing property improving method of the present invention can be used in various ways by suppressing the phenomenon of dye appearing on the surface of the powder of the resin composition, especially during transportation, use or storage at high temperatures. This improves the dyeability of the. 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.)”.

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

[Preparation Example 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), Carnauba wax C1 (4 parts) are 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.
In addition, the dye represented by the following formula (1) was synthesized by the method described in JP-A No. 6-184481.

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

[Preparation Example 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 Preparation Example 2 (Step 1), H05TM (1.5 parts) manufactured by Clariant Japan, TG-811F (1.5 parts) manufactured by Cabot, and Titanium Industry Co., Ltd. Of SW-100 (1.0 part) was placed in a Henschel mixer and stirred at a rotational speed of 30 m / sec for 10 minutes to prepare a cyan toner.

[Preparation Example 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 Preparation Example 3 (Step 1), H05TM (1.5 parts) manufactured by Clariant Japan, TG-811F (1.5 parts) manufactured by Cabot, and Titanium Industry Co., Ltd. Of SW-100 (1.0 part) 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.

[Preparation Example 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, premixed for 10 minutes at a rotational speed of 30 m / sec, and then twin screw extrusion The mixture 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 Preparation Example 4 (Step 1), H05TM (1.5 parts) manufactured by Clariant Japan, TG-811F (1.5 parts) manufactured by Cabot, and Titanium Industry Co., Ltd. Of SW-100 (1.0 part) was placed 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 dendritic composition prepared as described above in acetone is shown in Table 1 below.
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.

  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 1.

  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 2 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 superimposing the toner adhesion surface of each obtained intermediate recording medium and a double picket (weight per unit area: 90 g / m ² ) made of 100% polyester fiber as a dyed object, a heat press machine (manufactured by Taiyo Seiki Co., Ltd.) : Using a transfer press machine TP-600A2), heat treatment was performed under the conditions of 195 ° C. × 60 seconds to obtain dyed products of the 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 the double picket before dyeing in the same manner). The evaluation results are shown in Table 2 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 2 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 2 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.

  As is apparent from Table 2, it was found that each example improved all dyeing properties to the same or better level as compared with each comparative example.

  The dyeing property improving method of the present invention contains a dye used for direct dyeing by electrophotographic method, sublimation transfer dyeing, etc., because the dyeing concentration is high and can suppress dyeing of white background contamination and dyeing unevenness. In dyeing or printing using powder toner, powder paint, or the like, it is extremely useful as a method for obtaining a high-quality dyed product or printed product without image defects.

Claims (4)

  A method for improving dyeability in a dyeing method in which a powder toner of a resin composition used in a dry non-magnetic one-component developing system containing at least a resin and two kinds of dyes is used as a colorant. Among them, at least one dye is a disperse dye or oil-soluble dye having a solubility in acetone of 0.04 g / 100 ml to 0.07 g / 100 ml.   A powder toner of a resin composition for use in a dry non-magnetic one-component developing system, which contains at least a resin and two kinds of dyes, which is used in the method for improving dyeability according to claim 1, wherein the two kinds of dyes are used. Among them, the powder of the resin composition, wherein at least one dye is a disperse dye or an oil-soluble dye having a solubility in acetone of 0.04 g / 100 ml to 0.07 g / 100 ml.   A dyeing method using the powder toner of the resin composition according to claim 2.   A dyeing method using a powder toner of a resin composition containing at least a resin and two kinds of dyes used for a dry non-magnetic one-component developing method as a colorant is an intermediate between a powder toner of a resin composition by an electrophotographic method. 2. The sublimation transfer dyeing method according to claim 1, wherein the dye is attached to a recording medium, and dyeing is performed by sublimation-transferring a dye contained in the powder of the resin composition attached to the intermediate recording medium to a dyed object. To improve the dyeing property of shampoo.