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WO2015020165A1 - Poudre, procédé permettant d'éviter l'agglomération de poudre et procédé permettant d'améliorer des propriétés colorantes - Google Patents

Poudre, procédé permettant d'éviter l'agglomération de poudre et procédé permettant d'améliorer des propriétés colorantes Download PDF

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Publication number
WO2015020165A1
WO2015020165A1 PCT/JP2014/070928 JP2014070928W WO2015020165A1 WO 2015020165 A1 WO2015020165 A1 WO 2015020165A1 JP 2014070928 W JP2014070928 W JP 2014070928W WO 2015020165 A1 WO2015020165 A1 WO 2015020165A1
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WO
WIPO (PCT)
Prior art keywords
dyes
powder
dye
resin composition
disperse
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2014/070928
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English (en)
Japanese (ja)
Inventor
諒 寺西
慎介 清水
鈴木　祐司
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Nippon Kayaku Co Ltd
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Nippon Kayaku Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
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Priority to JP2015530961A priority Critical patent/JPWO2015020165A1/ja
Publication of WO2015020165A1 publication Critical patent/WO2015020165A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0041—Optical brightening agents, organic pigments
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L101/00—Compositions of unspecified macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0001—Post-treatment of organic pigments or dyes
    • C09B67/0002—Grinding; Milling with solid grinding or milling assistants
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/0092—Dyes in solid form
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G9/00—Developers
    • G03G9/08—Developers with toner particles
    • G03G9/0802—Preparation methods
    • G03G9/0804—Preparation methods whereby the components are brought together in a liquid dispersing medium
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G9/00—Developers
    • G03G9/08—Developers with toner particles
    • G03G9/0802—Preparation methods
    • G03G9/0812—Pretreatment of components
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G9/00—Developers
    • G03G9/08—Developers with toner particles
    • G03G9/09—Colouring agents for toner particles
    • G03G9/0906—Organic dyes
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G9/00—Developers
    • G03G9/08—Developers with toner particles
    • G03G9/09—Colouring agents for toner particles
    • G03G9/0906—Organic dyes
    • G03G9/091—Azo dyes
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G9/00—Developers
    • G03G9/08—Developers with toner particles
    • G03G9/09—Colouring agents for toner particles
    • G03G9/0906—Organic dyes
    • G03G9/0914—Acridine; Azine; Oxazine; Thiazine-;(Xanthene-) dyes
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G9/00—Developers
    • G03G9/08—Developers with toner particles
    • G03G9/09—Colouring agents for toner particles
    • G03G9/0906—Organic dyes
    • G03G9/0916—Quinoline; Polymethine dyes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K2201/00—Specific properties of additives
    • C08K2201/014—Additives containing two or more different additives of the same subgroup in C08K

Definitions

  • 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.
  • 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.
  • 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.
  • 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).
  • 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 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.
  • 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
  • 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.
  • the toner according to (6) which is used for suppressing powder aggregation or used as a colorant in a method for improving dyeability.
  • (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.
  • 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.
  • 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".
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • the “powder” of the resin composition is used in the meaning including all powders having various shapes such as particles.
  • propylene glycol monomethyl ether acetate means propylene glycol-1-monomethyl ether-2-acetate, and may be abbreviated as “PGMEA” in this specification.
  • 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.
  • 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.
  • 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.
  • the solubility in PGMEA is 0.04 g / 100 ml to 20 g /
  • 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 resin composition powder contains two or more dyes
  • at least one of the dyes is a sublimation dye
  • the dispersion thereof has a solubility in PGMEA of 0.04 g / 100 ml to 20 g / 100 ml.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • water-insoluble dye means a dye that is insoluble or hardly soluble in water.
  • lightly 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.
  • 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.
  • Yellow dyes such as Reactive Yellow 2, 3, 18, 81, 84, 85, 95, 99, 102
  • Orange dyes such as Reactive Orange 5, 9, 12, 13, 35, 45, 99
  • I. Brown dyes such as Reactive Brown 2, 8, 9, 17,
  • 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;
  • 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.
  • 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.
  • 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;
  • 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;
  • 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 .;
  • And green dyes such as Mordant Green 1, 3, 4, 5, 10, 15, 19, 26, 29, 33, 34, 35, 41, 43, and 53;
  • 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;
  • 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.
  • 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.
  • Orange dyes such as C., 96, 97, 118, 119, 127, 130, 139, 142; I.
  • 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.
  • Yellow dyes such as Solvent Yellow 9, 17, 19, 21, 24, 31, 35, 43, 44, 58, 61, 80, 93, 100, 102, 103, 105,
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • styrene or styrene derivative polymer examples include polystyrene, poly p-chlorostyrene, and polyvinyltoluene.
  • styrene copolymer examples 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- ⁇ -chloromethyl methacrylate copolymer, styrene-acrylonitrile copolymer, styrene- Vinyl methyl ketone copolymer, styrene-butadiene Polymers, styrene - isoprene copolymer, styrene - acrylonit
  • 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.
  • 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. .
  • 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.
  • 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.
  • the powder of the resin composition can be used for various applications as described above.
  • the powder of this resin composition may contain additives other than resin according to the use application.
  • 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.
  • the powder of the resin composition 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.
  • 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.
  • 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.
  • 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.
  • 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 ⁇ m.
  • the dye represented by the following formula (1) was synthesized by the method described in JP-A-6-184481.
  • Example A-1 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 ⁇ m.
  • the dye represented by the following formula (2) was synthesized by the method described in JP-A-6-228444.
  • Example A-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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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).
  • a dry non-magnetic one-component developing type printer Katsukawa Electric Co., Ltd .: KIPc7800.
  • 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.
  • 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 evaluation results are shown in Table 5 below.
  • Evaluation Test 4 [Visual Evaluation of Dyeing Contamination on White Background]
  • 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.
  • 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.
  • 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.

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Abstract

Le problème à résoudre dans le cadre de la présente invention consiste à fournir : une poudre d'une composition de résine comprenant au moins une résine et deux types de colorants ; un procédé permettant d'éviter l'agglomération de poudre dans la poudre de la composition de résine ; et un procédé permettant d'améliorer des propriétés colorantes dans un procédé de coloration utilisant la poudre de la composition de résine en tant qu'agent colorant. La solution de l'invention consiste en une poudre d'une composition de résine qui comprend au moins une résine et deux types de colorants, au moins un des deux types de colorants étant un colorant dispersé ou un colorant liposoluble, dont la solubilité dans l'acétate de 2-méthoxy-1-méthyléthyle représente de 0,04 g/100 ml à 20 g/100 ml.
PCT/JP2014/070928 2013-08-09 2014-08-07 Poudre, procédé permettant d'éviter l'agglomération de poudre et procédé permettant d'améliorer des propriétés colorantes Ceased WO2015020165A1 (fr)

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US10942464B2 (en) 2017-03-20 2021-03-09 Esprix Technologies, LP. Ames negative sublimation toner

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JP2010160172A (ja) * 2009-01-06 2010-07-22 Konica Minolta Business Technologies Inc 静電荷像現像用トナーおよび画像形成方法
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US10942464B2 (en) 2017-03-20 2021-03-09 Esprix Technologies, LP. Ames negative sublimation toner

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