WO2015016015A1 - Composé trisazo conférant une couleur noire, composition de colorant conférant une couleur noire contenant ledit composé, et utilisation associée - Google Patents

Composé trisazo conférant une couleur noire, composition de colorant conférant une couleur noire contenant ledit composé, et utilisation associée Download PDF

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Publication number
WO2015016015A1
WO2015016015A1 PCT/JP2014/068156 JP2014068156W WO2015016015A1 WO 2015016015 A1 WO2015016015 A1 WO 2015016015A1 JP 2014068156 W JP2014068156 W JP 2014068156W WO 2015016015 A1 WO2015016015 A1 WO 2015016015A1
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WIPO (PCT)
Prior art keywords
salt
parts
dye composition
dye
group
Prior art date
Application number
PCT/JP2014/068156
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English (en)
Japanese (ja)
Inventor
桂丈 佐々木
信孝 山本
Original Assignee
日本化薬株式会社
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Priority to JP2015529484A priority Critical patent/JP6198349B2/ja
Publication of WO2015016015A1 publication Critical patent/WO2015016015A1/fr

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Classifications

    • 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
    • C09B33/00—Disazo and polyazo dyes of the types A->K<-B, A->B->K<-C, or the like, prepared by diazotising and coupling
    • C09B33/18—Trisazo or higher polyazo dyes
    • C09B33/22—Trisazo dyes of the type A->B->K<-C
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/02—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using azo dyes
    • D06P1/04—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using azo dyes not containing metal
    • D06P1/06—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using azo dyes not containing metal containing acid groups
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/39—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using acid dyes
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/58—Material containing hydroxyl groups
    • D06P3/60—Natural or regenerated cellulose
    • D06P3/6008—Natural or regenerated cellulose using acid dyes
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/58—Material containing hydroxyl groups
    • D06P3/60—Natural or regenerated cellulose
    • D06P3/62—Natural or regenerated cellulose using direct dyes

Definitions

  • the present invention relates to a black trisazo compound or a salt thereof, a black dye composition containing the same, a dyeing method using the same, and a dyed product thereof.
  • direct dyes having good dyeing properties are often used.
  • C.I. I. Direct Black 19 and C.I. I. Direct Black 168 is often used.
  • these dyes have low light resistance and are positive in the Ames test known as the mutagenicity test. If the Ames test is positive, it is considered that there is a risk of adverse effects on the human body and the environment, and the use and production must be performed under extremely strict protective equipment. There are many problems in terms of production efficiency.
  • Ames test negative dyes have been developed from the viewpoint of safe operation of plants and environmental protection, but there are still many problems to be overcome such as few dyes with dyeing and light fastness.
  • Ames test negative dye compositions and dyed products thereof are required to have improved light resistance, but no satisfactory dye or dye composition has been found at present. (See Patent Documents 1 to 3 and Non-Patent Document 1).
  • the present inventors have found a novel black azo dye having a negative Ames test and a dye composition containing the same, leading to the present invention. That is, the present invention relates to the following 1) to 8).
  • a trisazo compound represented by the following formula (1) or a salt thereof [Wherein, R 1 represents a hydrogen atom, a hydroxy group, or a sulfonic acid group, and A represents a substituent represented by the following formula (2). ] [Wherein R 2 represents a hydrogen atom, a hydroxy group, a sulfonic acid group, or a carboxy group. ]
  • a method for dyeing a cellulose fiber material comprising a step of dyeing the cellulose fiber material using the dye composition described in 5) or 6) above.
  • the trisazo compound or a salt thereof of the present invention that can be used as a black dye has a negative Ames test and can dye cellulose fiber materials, particularly paper and pulp, at a high concentration. Moreover, the dyed material dye
  • the trisazo compound of the present invention or a salt thereof is a trisazo compound represented by the above formula (1) or a salt thereof, and A in the formula is represented by the above formula (2).
  • the bonding position of R 1 in the above formula (1) is not particularly limited as long as the bonding position of the naphthyl group to be bonded is, but is preferably 1-position or 2-position, and more preferably 2-position.
  • the bonding position of A in the above formula (1) is not particularly limited as long as the naphthyl group to be bonded can be bonded, but is preferably 6-position or 7-position, and more preferably 7-position.
  • the bonding position of R 2 in the above formula (2) is not particularly limited as long as it can be bonded to the phenyl group to which it is bonded, but is preferably the 3-position or 4-position, particularly preferably a hydrogen atom or 4-carboxy group, A hydrogen atom is more preferable.
  • the substitution position of the substituent is as indicated by a subscript in each chemical formula.
  • the azo group may be syn type, anti type or a mixture thereof.
  • the trisazo compound represented by the above formula (1) may be used as a free acid or a salt of a trisazo compound.
  • the salt of the trisazo compound include salts of acidic groups such as sulfonic acid groups.
  • the salt of the acidic group include alkali metal salts such as lithium salt, sodium salt and potassium salt, and organic salts such as ammonium salt and amine salt.
  • sodium salt is preferable.
  • trisazo compound of the present invention compounds described in Examples below are particularly preferable.
  • the dye composition containing the trisazo compound of the present invention or a salt thereof is also included in the present invention.
  • the dye composition may contain, for example, a solvent such as water and an additive used in a normal dye composition.
  • the additive include ethanol, triethanolamine, diethanolamine, proxel GXL, urea and the like.
  • the dye composition of the present invention may contain other direct dyes as long as the effects of the present invention are not impaired.
  • the direct dye is not particularly limited. I. Direct Orange 39, C.I. I. Direct Yellow 86, C.I. I. Direct Red 225, and C.I. I.
  • One or two dyes selected from the group consisting of Direct Red 83: 1 are preferably blended. These dyes are preferably incorporated in the dye composition in an amount of about 0.04 to 20% by mass. These dyes can be produced according to known literature, but commercially available dyes can also be used.
  • the dye composition of the present invention can be used for dyeing cellulose fiber materials, particularly paper and pulp, and in particular, a dyeing method using a solution of the dye composition, and a dyed product dyed by the dyeing method It is included in the present invention.
  • the solution is preferably an aqueous solution, and can be obtained by dissolving or diluting the trisazo compound of the present invention or a salt thereof or a dye composition containing it.
  • the dyeing method include a dyeing method under normal dyeing conditions for dyeing paper and pulp, a surface coating dyeing method including a size press method and a coating method, an internal dyeing method, and the like.
  • the dyed product includes paper and pulp dyed by the dyeing method of the present invention and articles obtained by processing the same.
  • the trisazo compound represented by the above formula (1) or a salt thereof is produced, for example, by performing a diazotization reaction and a coupling reaction in accordance with a conventional azo dye production method as described in Non-Patent Document 1. Is done.
  • R 1 and A used as appropriate in the following formulas (7), (9), and (10) have the same meaning as described above.
  • the compound represented by the following formula (3) is diazotized, and the compound represented by the following formula (4) and 0 to 40 ° C., preferably 10 to 15 ° C., pH 0.5 to 11, preferably pH 4.0.
  • a coupling reaction is carried out at ⁇ 5.0 to obtain a monoazo compound represented by the following formula (5).
  • a compound represented by the following formula (6) is diazotized to form a compound represented by the following formula (7) with 0 to 40 ° C., preferably 20 to 25 ° C., pH 0.5 to 11, preferably pH 8.0.
  • a coupling reaction is carried out at ⁇ 8.5 to obtain a monoazo compound represented by the following formula (9).
  • the monoazo compound represented by the above formula (5) is diazotized and mixed with the monoazo compound represented by the above formula (9) at 0 to 40 ° C., preferably 20 to 25 ° C., pH 0.5 to 11, preferably pH 8
  • the trisazo compound (10) represented by the following formula (10) of the present invention is obtained by a coupling reaction at .5 to 9.5.
  • the diazotization reaction may be carried out according to a conventional method in which a nitrite such as sodium nitrite is mixed in a mineral acid aqueous solution or suspension of the component to be diazotized, such as hydrochloric acid or sulfuric acid, Alternatively, the nitrite is added to a weakly alkaline aqueous solution, and a mineral acid is mixed with the nitrite.
  • the diazotization reaction may be performed at ⁇ 10 to 40 ° C.
  • the azo compound obtained by the coupling reaction may be taken out as it is or precipitated by aciding out or salting out and filtered, or may be taken to the next step as a solution or suspension.
  • the diazonium salt is hardly soluble and is in a suspension, it can be filtered and used as a press cake for the next coupling reaction.
  • salting out may be repeated or precipitated from water using an organic solvent.
  • the organic solvent include water-soluble organic solvents such as alcohols such as methanol and ethanol, and ketones such as acetone.
  • the resulting diazotized suspension was added dropwise to the dissolved solution at a temperature of 10 to 15 ° C. over about 30 minutes.
  • the pH of the reaction solution was maintained at 4.0 to 5.0 by adding an aqueous sodium carbonate solution.
  • the mixture was stirred at 5 to 10 ° C. and pH 4.0 to 5.0 for 5 hours, and further stirred overnight to complete the reaction.
  • sodium chloride was added to the reaction solution for salting out, followed by filtration, washing with water, and drying to obtain 15 parts of a compound represented by the above formula (5).
  • the pH value of the reaction solution was maintained at pH 8.5 to 9.5 by adding an aqueous sodium hydrogen carbonate solution.
  • the mixture was stirred for 3 hours while maintaining 20 to 25 ° C. and pH 9.0 to 9.5, and further stirred overnight to complete the reaction.
  • sodium chloride was added to the reaction solution for salting out, or acid precipitation with 35% hydrochloric acid, filtration, washing with water and drying to obtain 28 parts of the compound represented by the above formula (13).
  • Example 2 A dye bath was prepared by dissolving 0.210 parts of the dye synthesized in Example 1 in 1000 parts of water. After adding 300 parts of beating kraft pulp (30 parts of absolutely dry pulp, beating degree 35SR) to this dyeing bath and stirring for 15 minutes at room temperature, 1 part of rosin size (30% aqueous solution) is added and stirring is further performed for 10 minutes. 3 parts of aluminum sulfate was added and stirred for 20 minutes. The dyed pulp was paper-made and dried to obtain a black dyed product.
  • the trisazo compound for black whose Ames test of the present invention is negative shows slightly better dyeability and light resistance equivalent to the conventional dye A whose Ames test is positive, and is currently widely used. Compared to the known dye B, it shows slightly better dyeability and excellent light resistance.
  • Example 3 0.108 parts of the dye synthesized in Example 1 and 0.078 parts of C.I. I. Direct Orange 39 was blended and dissolved in 1000 parts of water to prepare a dye bath. After adding 300 parts of beating kraft pulp (30 parts of absolutely dry pulp, beating degree 35SR) to this dyeing bath and stirring for 15 minutes at room temperature, 1 part of rosin size (30% aqueous solution) is added and stirring is further performed for 10 minutes. 3 parts of aluminum sulfate was added and stirred for 20 minutes. The dyed pulp was paper-made and dried to obtain a black dyed product. COLOR EYE CE3000 (Macbeth) and visual color measurement were performed on the obtained dyed product, and color measurement device determination and visual determination by blue scale comparison were performed.
  • Example 3 shows the results of dyeability and light resistance. Table 3 also shows the results of dyeability and light resistance of the dyed product obtained by the above comparative example.
  • Example 4 0.108 parts of the dye synthesized in Example 1 and 0.066 parts of C.I. I. Direct Orange 39 and 0.006 parts C.I. I. Direct Red 83: 1 was blended and dissolved in 1000 parts of water to prepare a dye bath. After adding 300 parts of beating kraft pulp (30 parts of absolutely dry pulp, beating degree 35SR) to this dyeing bath and stirring for 15 minutes at room temperature, 1 part of rosin size (30% aqueous solution) is added and stirring is further performed for 10 minutes. 3 parts of aluminum sulfate was added and stirred for 20 minutes. The dyed pulp was paper-made and dried to obtain a black dyed product.
  • COLOR EYE CE3000 Macbeth
  • visual color measurement were performed on the obtained dyed product, and color measurement device determination and visual determination by blue scale comparison were performed. Further, a light resistance test was conducted in the same manner as in Example 2. There was no difference in light resistance with time. Table 3 shows the results of dyeability and light resistance.
  • Example 5 0.108 parts of the dye synthesized in Example 1 and 0.042 parts of C.I. I. Direct Orange 39 and 0.003 parts C.I. I. Direct Red 225 was blended and dissolved in 1000 parts of water to prepare a dye bath. After adding 300 parts of beating kraft pulp (30 parts of absolutely dry pulp, beating degree 35SR) to this dyeing bath and stirring for 15 minutes at room temperature, 1 part of rosin size (30% aqueous solution) is added and stirring is further performed for 10 minutes. 3 parts of aluminum sulfate was added and stirred for 20 minutes. The dyed pulp was paper-made and dried to obtain a black dyed product.
  • COLOR EYE CE3000 Macbeth
  • visual color measurement were performed on the obtained dyed product, and color measurement device determination and visual determination by blue scale comparison were performed. Further, a light resistance test was conducted in the same manner as in Example 2. There was no difference in light resistance with time. Table 3 shows the results of dyeability and light resistance.
  • the trisazo compound for black whose Ames test of the present invention is negative shows a slightly good dyeing result as compared with the conventional dye A whose Ames test is positive, and shows the same light resistance. Yes.
  • the dyeing result is slightly better than that of the known dye B, which is widely used at present, and the light resistance is excellent.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Paper (AREA)
  • Coloring (AREA)

Abstract

La présente invention concerne un composé trisazo ou un sel associé représenté par la formule (1) utilisé comme un excellent colorant azoïque conférant une couleur noire à un matériau de fibre de cellulose, et un papier et une pâte en particulier, ayant de bonnes propriétés de teinture et de solidité à la lumière, et dans lequel un test d'Ames est négatif. L'invention concerne également une composition de colorant contenant le composé trisazo ou un sel associé. Dans la formule (1), R1 représente un atome d'hydrogène, un groupe hydroxyle, ou une fonction acide sulfonique ; et A représente un groupe substituant représenté par la formule (2). Dans la formule (2), R2 représente un atome d'hydrogène, un groupe hydroxyle, une fonction acide sulfonique, ou un groupe carboxyle.
PCT/JP2014/068156 2013-08-01 2014-07-08 Composé trisazo conférant une couleur noire, composition de colorant conférant une couleur noire contenant ledit composé, et utilisation associée WO2015016015A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2015529484A JP6198349B2 (ja) 2013-08-01 2014-07-08 黒色用トリスアゾ化合物、それを含む黒色用染料組成物およびその使用

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JP2013160347 2013-08-01
JP2013-160347 2013-08-01

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WO2015016015A1 true WO2015016015A1 (fr) 2015-02-05

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Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH07224238A (ja) * 1994-02-15 1995-08-22 Mitsubishi Chem Corp 近赤外光読みとり用記録液、それを用いた記録方法及び近赤外光により情報を読みとる方法
JPH0892494A (ja) * 1994-09-27 1996-04-09 Orient Chem Ind Ltd トリスアゾ染料およびこれらを含有する水性インキ組成物
JP2001288379A (ja) * 2000-04-07 2001-10-16 Nippon Kayaku Co Ltd 水溶性トリスアゾ化合物、水性インク組成物及び着色体
JP2003518141A (ja) * 1998-07-13 2003-06-03 チバ スペシャルティ ケミカルズ ホールディング インコーポレーテッド 反応性染料、その製造およびその使用
JP2006076908A (ja) * 2004-09-08 2006-03-23 Nippon Kayaku Co Ltd ポリアゾ化合物の製造方法
JP2009132794A (ja) * 2007-11-30 2009-06-18 Nippon Kayaku Co Ltd アゾ化合物、インク組成物、記録方法及び着色体
JP2009536240A (ja) * 2006-05-09 2009-10-08 フジフィルム・イメイジング・カラランツ・リミテッド トリスアゾ化合物、組成物及びインクジェット印刷方法

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH07224238A (ja) * 1994-02-15 1995-08-22 Mitsubishi Chem Corp 近赤外光読みとり用記録液、それを用いた記録方法及び近赤外光により情報を読みとる方法
JPH0892494A (ja) * 1994-09-27 1996-04-09 Orient Chem Ind Ltd トリスアゾ染料およびこれらを含有する水性インキ組成物
JP2003518141A (ja) * 1998-07-13 2003-06-03 チバ スペシャルティ ケミカルズ ホールディング インコーポレーテッド 反応性染料、その製造およびその使用
JP2001288379A (ja) * 2000-04-07 2001-10-16 Nippon Kayaku Co Ltd 水溶性トリスアゾ化合物、水性インク組成物及び着色体
JP2006076908A (ja) * 2004-09-08 2006-03-23 Nippon Kayaku Co Ltd ポリアゾ化合物の製造方法
JP2009536240A (ja) * 2006-05-09 2009-10-08 フジフィルム・イメイジング・カラランツ・リミテッド トリスアゾ化合物、組成物及びインクジェット印刷方法
JP2009132794A (ja) * 2007-11-30 2009-06-18 Nippon Kayaku Co Ltd アゾ化合物、インク組成物、記録方法及び着色体

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JP6198349B2 (ja) 2017-09-20
JPWO2015016015A1 (ja) 2017-03-02

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