WO2023286282A1 - Fire retardant and simultaneously dyeing method for polyester-based textile - Google Patents

Fire retardant and simultaneously dyeing method for polyester-based textile Download PDF

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Publication number
WO2023286282A1
WO2023286282A1 PCT/JP2021/026874 JP2021026874W WO2023286282A1 WO 2023286282 A1 WO2023286282 A1 WO 2023286282A1 JP 2021026874 W JP2021026874 W JP 2021026874W WO 2023286282 A1 WO2023286282 A1 WO 2023286282A1
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represented
formula
red disperse
quinone
disperse dye
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PCT/JP2021/026874
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French (fr)
Japanese (ja)
Inventor
愛子 竹本
輝文 岩城
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大京化学株式会社
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Priority to PCT/JP2021/026874 priority Critical patent/WO2023286282A1/en
Priority to JP2023534574A priority patent/JPWO2023286282A1/ja
Publication of WO2023286282A1 publication Critical patent/WO2023286282A1/en

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    • 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
    • D06P1/16—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 dispersed, e.g. acetate, dyestuffs
    • D06P1/18—Azo 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
    • 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
    • D06P1/16—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 dispersed, e.g. acetate, dyestuffs
    • D06P1/20—Anthraquinone 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
    • 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
    • D06P1/44—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 insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/667—Organo-phosphorus compounds
    • 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
    • D06P3/34—Material containing ester groups
    • D06P3/52—Polyesters
    • D06P3/54—Polyesters using dispersed dyestuffs

Definitions

  • the present invention relates to a method for dyeing and simultaneously flame-retarding polyester fiber products, and more specifically, immersing a polyester fiber product in a processing bath containing a specific quinone red disperse dye and a specific flame retardant, and heating under pressure.
  • a method for simultaneously dyeing and flame-retarding a polyester fiber product which can obtain a dyed and flame-retardant polyester fiber product with good dyeing reproducibility by subjecting the polyester fiber product to flame-retardant treatment at the same time as dyeing.
  • the present invention relates to dyed, flame-retardant polyester fiber articles thus obtained.
  • the quinone-based red disperse dye represented by is known to give a disperse dye composition having a higher degree of light fastness by combining with a specific yellow disperse dye (see, for example, Patent Document 1).
  • the quinone-based red disperse dye represented by is conventionally known to give a dyed product with excellent light fastness (see Patent Document 2).
  • the quinone-based red disperse dye represented by is also known to give a disperse dye composition with improved light fastness by combining these with a specific quinophthalone-based disperse dye (see, for example, Patent Document 3) ).
  • azo disperse dyes are generally known to be inferior to quinone disperse dyes in light fastness, but to have strong coloring power.
  • the azo red disperse dye represented by is known to give various dyes with excellent fastness by combining it with other azo red disperse dyes having different structures (for example, patent documents 4).
  • red, yellow and blue disperse dyes as the three primary colors according to the desired color tone, and to mix these colors.
  • the dyeing characteristics of these red, yellow and blue disperse dyes, particularly the dyeing speed, that is, the rate of increase in the amount of dyeing accompanying the temperature rise during dyeing are uniform, the dyeing conditions, such as Even if the dyeing temperature fluctuates to a certain extent, the resulting dyed goods have little effect on the shade. That is, the disperse dyes of the three primary colors with uniform dyeing speeds are excellent in reproducibility of dyeing of polyester fiber products.
  • the polyester textiles are immersed in a processing bath containing a flame retardant together with a quinone red disperse dye and heated to dye the polyester textiles, and at the same time, the flame retardant Even when performing flame retardant processing, depending on the flame retardant used, even if dyeing is performed under the same conditions, compared to dyeing polyester textiles with a quinone red disperse dye in the absence of a flame retardant. As a result, the dyeing speed of the red disperse dye fluctuates, and the color tone and color density of the resulting dyed product change significantly. .
  • the quinone red disperse dye used has a good dyeing reproducibility.
  • the flame retardant to be used must not only be excellent in color reproducibility, but must also not interfere with the excellent dyeing reproducibility of the quinone red disperse dye used in combination.
  • a method for simultaneously dyeing and flame-retarding a polyester fiber article comprising immersing the polyester fiber article in a processing bath containing a phosphoric acid ester amide represented by and heating the polyester fiber article.
  • the above method may be referred to as the first method.
  • the above method may be referred to as the second method.
  • the polyester fiber product is immersed in the processing bath and heated to 105° C. or higher, and the processing bath preferably contains the quinone red dispersion to be used. It contains a dye in a concentration range of 0.05 to 5% owf, and the phosphate ester amide in a concentration range of 0.5 to 10% owf.
  • the polyester fiber product is immersed in the processing bath and heated to 105° C. or higher.
  • the total concentration of the dye and the azo red disperse dye is in the range of 0.05 to 5% wf, and the phosphate ester amide is in the concentration range of 0.5 to 10% wf.
  • the red disperse dye to be used regardless of whether it is a quinone-based or azo-based red disperse dye, and both of the phosphoric acid ester amides have an average particle size of It is preferable that the diameter is in the range of 0.2 to 2.0 ⁇ m.
  • a dyed flame-retardant polyester fiber product containing the red disperse dye and the flame retardant phosphate ester amide.
  • the dyeing and simultaneous flame retardant processing method for polyester fiber products according to the present invention includes, together with the flame retardant phosphate ester amide represented by the formula (VII), At least one selected from the group consisting of the quinone red disperse dyes represented by the formulas (I) to (V), or consisting of the quinone red disperse dyes represented by the formulas (I) to (V) Using at least one selected from the group and the azo red disperse dye represented by the formula (VI), a polyester fiber product is dyed and at the same time subjected to flame retardant treatment.
  • the flame retardant phosphate ester amide represented by the formula (VII) At least one selected from the group consisting of the quinone red disperse dyes represented by the formulas (I) to (V), or consisting of the quinone red disperse dyes represented by the formulas (I) to (V)
  • a polyester fiber product is dyed and at the same time subjected to flame retardant treatment.
  • the present invention together with the flame retardant phosphate amide of formula (VII), at least one of the quinone red disperse dyes of formulas (I) to (V), or Dyeing and simultaneously flame retarding a polyester fiber product in a processing bath containing at least one of the quinone red disperse dyes represented by I) to (V) and the azo red disperse dye represented by the above formula (VI)
  • the dyeing rate of the red disperse dye is small, so that the dyed flame-retardant polyester fiber product can be obtained with good dyeing reproducibility.
  • the method for dyeing and simultaneously flame-retarding a polyester fiber product according to the present invention is at least one of the quinone red disperse dyes represented by the above formulas (I) to (V), or the above formulas (I) to (V).
  • the flame-retardant treatment is carried out at the same time as dyeing by immersing and heating the polyester-based textile product. According to such a method, the dyed flame-retardant polyester-based textile product can be obtained with good dyeing reproducibility.
  • At least one of the quinone red disperse dyes represented by the above formulas (I) to (V) or the above formula ( At least one of the quinone red disperse dyes represented by I) to (V) and the azo red disperse dye represented by the formula (VI) together with the phosphate ester amide represented by the formula (VII) include.
  • the quinone-based red disperse dye represented by the above formula (I) is C.I. I. Disperse Red 86.
  • the quinone-based red disperse dye represented by the formula (II) is C.I. I. Disperse Red 191
  • the quinone-based red disperse dye represented by the above formula (III) is C.I. I. Disperse Red 92
  • the quinone-based red disperse dye represented by the above formula (IV) is C.I. I. Disperse Red 53
  • the quinone-based red disperse dye represented by the above formula (V) is C.I. I. Disperse Red 60.
  • the azo red disperse dye represented by the formula (VI) is C.I. I. Disperse Red 167:1.
  • the quinone-based red disperse dye, or the quinone-based red disperse dye and the azo-based red disperse dye, and the flame retardant phosphate ester amide are used to perform dyeing and simultaneous flame retardancy on the polyester fiber product.
  • both the red disperse dye and the flame retardant phosphate ester amide are 0.2 It preferably has an average particle size of ⁇ 2.0 ⁇ m.
  • the red disperse dye and the flame retardant phosphate ester amide need not have the same average particle size.
  • the red disperse dye and the phosphate ester amide having an average particle size within the range described above can be obtained, for example, by pulverizing the red disperse dye and the phosphate ester amide in advance with a sand mill or a ball mill in water containing a surfactant. can be obtained by
  • surfactants used for refining the red disperse dye include formalin condensates of naphthalenesulfonic acid and alkylbenzenesulfonic acid, formalin condensates of naphthalenesulfonic acid, and cresol and 2-naphthol-6-sulfonic acid.
  • Formalin condensates formalin condensates of alkylnaphthalene sulfonic acid, formalin condensates of creosote oil sulfonic acid, anionic surfactants such as lignin sulfonic acid, block copolymers of ethylene oxide and propylene oxide, ethylene oxide adducts of alkylphenols
  • anionic surfactants such as ethylene oxide adducts of polystyrenated phenols, and mixtures of these anionic surfactants and nonionic surfactants are preferred.
  • surfactants used for refining the phosphoric acid ester amide include anionic surfactants such as sulfuric acid ester salts of arylated phenol ethylene oxide adducts and sulfosuccinic acid ester salts of styrenated phenol ethylene oxide adducts.
  • anionic surfactants such as sulfuric acid ester salts of arylated phenol ethylene oxide adducts and sulfosuccinic acid ester salts of styrenated phenol ethylene oxide adducts.
  • nonionic surfactants such as agents, block copolymers of ethylene oxide and propylene oxide, ethylene oxide adducts of alkylphenols, ethylene oxide adducts of polystyrenated phenols, or combinations of these anionic surfactants and nonionic surfactants Mixtures are preferred.
  • a specific red disperse dye and a specific flame retardant are wet pulverized in the presence of the surfactant, and the red dispersion A dispersion liquid containing fine particles of a dye and a flame retardant is added to a bath containing water to form a processing bath having a predetermined bath ratio. ° C.
  • polyester fiber product is removed from the processing bath, soaped, washed with water, dehydrated and dried to obtain a dyed flame-retardant polyester fiber product.
  • the polyester fiber product is immersed in the processing bath in the dyeing machine, heated to 105 ° C. or higher, and exhausted in the bath. is in the range of 0.1-0.5 MPa.
  • a polyester fiber product dyed with the red disperse dye and flame-retardant-treated with the flame retardant can be obtained.
  • the amounts of the quinone red disperse dye and the flame retardant phosphate ester amide used are not particularly limited, but the amount of the quinone red disperse dye used is usually 0.5. It is in the range of 05 to 5%owf, preferably in the range of 0.1 to 5%owf, more preferably in the range of 0.3 to 3.0%owf.
  • the amount of the flame retardant phosphate ester amide used is preferably in the range of 0.5 to 10% owf in order to impart sufficient flame retardancy to the dyed polyester fiber product, and 0.5 to A range of 8.0% owf is more preferred, and a range of 1.0 to 8.0% owf is most preferred.
  • the amounts of the quinone red disperse dye, the azo red disperse dye and the flame retardant phosphate ester amide are not particularly limited, but the quinone red disperse dye And the amount of the azo red disperse dye used, in total amount, is usually in the range of 0.05 to 5% owf, preferably in the range of 0.1 to 5% owf, more preferably It ranges from 0.3 to 3.0%owf.
  • the amount of the flame retardant phosphate ester amide used is the same as above.
  • the bath ratio of the working bath is not particularly limited, but is usually in the range of 1:3 to 1:30, preferably in the range of 1:5 to 1:20. If the bath ratio is lower than 1:3, uneven dyeing may occur because the polyester fiber product is not sufficiently immersed in the processing bath. It is uneconomical because the amount of water used for processing is unnecessarily large.
  • polyester fiber products refer to fibers containing at least polyester fibers, and fabrics such as yarns, cotton, knitted and woven fabrics, and non-woven fabrics containing such fibers.
  • it refers to polyester fibers, yarns made from these fibers, cotton, and fabrics such as knitted and woven fabrics and non-woven fabrics.
  • the fabric such as a woven fabric or a non-woven fabric may be a single layer or a laminate of two or more layers, or may be a composite made of yarn, cotton, a woven fabric, a non-woven fabric, or the like.
  • the polyester fiber is, for example, polyethylene terephthalate, polypropylene terephthalate, polybutylene terephthalate, polyethylene naphthalate, polybutylene naphthalate, polyethylene terephthalate/isophthalate, polyethylene terephthalate/5-sulfoisophthalate, polyethylene terephthalate/polyoxy benzoyl, polybutylene terephthalate/isophthalate, poly(D-lactic acid), poly(L-lactic acid), copolymers of D-lactic acid and L-lactic acid, copolymers of D-lactic acid and aliphatic hydroxycarboxylic acids, Copolymers of L-lactic acid and aliphatic hydroxycarboxylic acids, polycaprolactones such as poly- ⁇ -caprolactone (PCL), polymalic acid, polyhydroxycarboxylic butyric acid, polyhydroxyvaleric acid, ⁇ -hydroxybutyric acid (3HB)-3 - Polyaliphatic
  • the dyed flame-retardant polyester fiber product obtained by the method of the present invention is suitably used for, for example, seat sheets, seat covers, curtains, wallpapers, ceiling cloths, carpets, drop curtains, architectural protection sheets, tents, canvases, and the like.
  • disperse dyes can be used in combination as long as the dyeing reproducibility of the flame retardant processing method for simultaneously dyeing polyester fiber products according to the present invention is not hindered.
  • disperse dyes include C.I. I. Disperse Yellow 71, 42, 51, C.I. I. Yellow disperse dyes such as Solvent Yellow 163, C.I. I. blue disperse dyes such as Disperse Blue 54, 60, 77, 165; I. Orange disperse dyes such as Disperse Orange 29 and 155 can be used, but the dyes are not limited to these.
  • both the red disperse dye and the flame retardant are wet-ground using a mill filled with glass beads with a diameter of 0.5 mm so as to have a predetermined average particle size in the presence of a surfactant. used as a dispersion.
  • the average particle size of both the disperse dye and the flame retardant was determined based on the particle size distribution of each dispersion measured by a laser diffraction particle size distribution analyzer SALD-2000J manufactured by Shimadzu Corporation. Refers to the volume-based median diameter.
  • CM-600d manufactured by Konica Minolta, Inc.
  • a polyester double picket (basis weight of 240 g/m 2 ) was used as a fabric to be treated, and this was obtained by dyeing with a disperse dye at a temperature of 100 ° C. in the absence of a flame retardant.
  • the color difference ⁇ E 100° C.
  • a dyed product obtained by dyeing a fabric with a disperse dye in the absence of a flame retardant at a temperature of 130 ° C. and a dyed product obtained by dyeing with the same disperse dye as above in the presence of a flame retardant were measured.
  • the color difference .DELTA.E 130.degree. C.
  • the color difference ⁇ E (dye + flame retardant) of the dyed product obtained by dyeing with each disperse dye at °C was determined.
  • the L * a * b * color specification formulated by the International Commission on Illumination (CIE) in 1974 According to the color space by the system.
  • CIE International Commission on Illumination
  • the L * value is called a brightness index, and a larger value indicates a brighter color, and a smaller value indicates a darker color.
  • White has an L * value of 100 and black has an L * value of 0.
  • the a * and b* values represent hue and saturation and are called chromaticity indices.
  • Example 1 A fabric to be treated (polyester double picket (basis weight: 240 g/m 2 ) into a processing bath with a bath ratio of 1:10 containing 0.3% owf of a red disperse dye with an average particle size of 0.8 ⁇ m represented by the formula (I) ) is added, the temperature is raised from 40 ° C. to 100 ° C. at a rate of 2 ° C. per minute, and the bath is exhausted, then soaped and washed with water, dehydrated and dried, and the dyed fabric. got This dyed fabric was colorimetrically measured to determine L * (100), a * (100) and b * (100).
  • the same treated fabric as above is put into a processing bath having the same structure as above, and the temperature is raised from 40 ° C. to 130 ° C. at a rate of 2 ° C. per minute, and held at that temperature for 30 minutes. It was exhausted in a bath, then soaped and washed with water, and then dehydrated and dried to obtain a dyed fabric. This dyed fabric was measured in the same manner as above to determine L * (130), a * (130) and b * (130).
  • the dyed fabric was measured in the same manner as described above to determine L * (100 flame retardant), a * (100 flame retardant) and b * (100 flame retardant).
  • the same treated fabric as above is put into a processing bath having the same structure as above, and the temperature is raised from 40 ° C. to 130 ° C. at a rate of 2 ° C. per minute, and held at that temperature for 30 minutes. It was exhausted in a bath, then soaped and washed with water, and then dehydrated and dried to obtain a dyed fabric.
  • the dyed fabric was measured in the same manner as above to determine L * (130 flame retardant), a * (130 flame retardant) and b * (130 flame retardant).
  • the color difference ⁇ E (100 ° C.) from the dyed fabric obtained by the formula ⁇ E (100 ° C.) [(L * (100) - L * (100 flame retardant)) 2 + (a * (100) - a * (100 flame retardant)) 2 + (b * (100) - b * (100 flame retardant)) 2 ] 1/2 .
  • the color difference ⁇ E (130 ° C.) from the dyed fabric obtained by the formula ⁇ E (130 ° C.) [(L * (130) - L * (130 flame retardant)) 2 + (a * (130) - a * (130 flame retardant)) 2 + (b * (130) - b * (130 flame retardant)) 2 ] 1/2 .
  • ⁇ E (100° C.) was evaluated as ⁇ (appropriate) when less than 5.00 and x (unsuitable) when 5.00 or more.
  • ⁇ E (130° C.) was evaluated as ⁇ (appropriate) when less than 5.00 and x (unsuitable) when 5.00 or more.
  • the dyeing speed change rate value exceeds 100 when ⁇ E (dye) is greater than ⁇ E (dye + flame retardant). That is, it can be said that the dyeing speed was increased by using the flame retardant together with the disperse dye.
  • ⁇ E(dye) is less than ⁇ E(dye+flame retardant)
  • the value is 100 or less. That is, it can be said that the dyeing speed is slowed down by using the flame retardant together with the disperse dye, so it can be said that the flame retardant inhibits the dyeing.
  • Example 2-5 instead of the red disperse dye represented by formula (I) having an average particle size of 0.8 ⁇ m, each of the formulas (II) to (V) represented by each of the above formulas (II) to (V) having an average particle size of 0.8 ⁇ m was used. A dyed fabric was obtained in the same manner except that an 8 ⁇ m red disperse dye was used.
  • Examples 6-10 In Examples 1 to 5, instead of the red disperse dye 0.3% owf having an average particle size of 0.8 ⁇ m represented by the formula (I), any of the formulas (I) to (V) respectively A dyed fabric was obtained in the same manner, except that 3.0% owf of a red disperse dye having an average particle size of 0.8 ⁇ m was used.
  • Examples 11-15 In Examples 1 to 5, instead of the flame retardant phosphoric acid ester amide 4.0% owf having an average particle size of 0.6 ⁇ m represented by the formula (VII), the average particles represented by the formula (VII) In the same manner as in Examples 1 to 5, except that 8.0% owf of a flame retardant phosphoric acid ester amide having a diameter of 0.6 ⁇ m was used, all of the average particle sizes represented by the formulas (I) to (V) A dyed fabric was similarly obtained using 0.8 ⁇ m red disperse dye 0.3% owf.
  • Examples 16-20 In Examples 1 to 5, instead of the flame retardant phosphoric acid ester amide 4.0% owf having an average particle size of 0.6 ⁇ m represented by the formula (VII), the average particles represented by the formula (VII) In the same manner as in Examples 1 to 5, except that 1.0% owf of a flame retardant phosphoric acid ester amide having a diameter of 0.6 ⁇ m was used, all of the average particle sizes represented by the formulas (I) to (V) A dyed fabric was similarly obtained using 0.8 ⁇ m red disperse dye 0.3% owf.
  • any of the quinone red disperse dyes having an average particle size of 0.8 ⁇ m represented by the formulas (I) to (V) and the average represented by the formula (VI) A dyed fabric was obtained in the same manner except that an azo red disperse dye having a particle size of 0.8 ⁇ m was used.
  • Example 1 instead of the flame retardant phosphate amide represented by the formula (VII), the following formula (VIII) having an average particle size of 0.6 ⁇ m was used as a flame retardant.
  • a dyed fabric was obtained in the same manner except that resorcinol bis (2,6-dixylenyl phosphate) represented by was used.
  • Example 2 instead of the flame retardant phosphate amide represented by the formula (VII), the following formula (IX) having an average particle size of 0.6 ⁇ m was used as a flame retardant.
  • the flame retardant phosphate amide represented by the formula (VII) instead of the flame retardant phosphate amide represented by the formula (VII), the following formula (IX) having an average particle size of 0.6 ⁇ m was used as a flame retardant.
  • a dyed fabric was obtained in the same manner except that 10-benzyl-9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide represented by was used.
  • Example 3 instead of the flame retardant phosphate amide represented by the formula (VII), the following formula (X) having an average particle size of 0.6 ⁇ m was used as a flame retardant.
  • a dyed fabric was obtained in the same manner except that 2-phenoxyethyl diphenyl phosphate represented by was used.
  • a dyed fabric was obtained in the same manner except that 5,5-dimethyl-2-(2'-phenylphenoxy)-1,3,2-dioxaphosphorinane-2-oxide represented by was used.
  • Example 1 instead of the flame retardant phosphate amide represented by the formula (VII), the following formula (XII) having an average particle size of 0.6 ⁇ m was used as the flame retardant.
  • the flame retardant phosphate amide represented by the formula (VII) instead of the flame retardant phosphate amide represented by the formula (VII), the following formula (XII) having an average particle size of 0.6 ⁇ m was used as the flame retardant.
  • a dyed fabric was obtained in the same manner except that p-cresyl phosphate represented by was used.
  • Example 6 instead of the flame retardant phosphate amide represented by the formula (VII), the following formula (XIII) having an average particle size of 0.6 ⁇ m was used as a flame retardant.
  • a dyed fabric was obtained in the same manner except that tris (2,3-dibromopropyl) isocyanurate represented by was used.
  • Comparative Examples 13-18 Dyed fabrics were obtained in the same manner as in Comparative Examples 1 to 6, except that the red disperse dye represented by formula (III) was used in place of the red disperse dye represented by formula (I).
  • Comparative Examples 19-24 Dyed fabrics were obtained in the same manner as in Comparative Examples 1 to 6, except that the red disperse dye represented by formula (IV) was used in place of the red disperse dye represented by formula (I).
  • Comparative Examples 25-30 Dyed fabrics were obtained in the same manner as in Comparative Examples 1 to 6, except that the red disperse dye represented by formula (I) was replaced with the red disperse dye represented by formula (V).
  • Comparative example 31 In Example 1, 3.0% owf of the red disperse dye represented by the formula (I) was used, and instead of the flame retardant represented by the formula (VII), the average represented by the formula (XIII) A dyed fabric was obtained in the same manner except that tris(2,3-dibromopropyl)isocyanurate with a particle size of 0.6 ⁇ m was used.
  • Comparative example 32 In Example 1, instead of the red disperse dye represented by formula (I), a red disperse dye 3.0% owf having an average particle size of 0.8 ⁇ m represented by formula (II) was used, and the formula In the same manner, except that resorcinol bis(2,6-dixylenyl phosphate) having an average particle size of 0.6 ⁇ m represented by the formula (VIII) was used instead of the flame retardant represented by (VII). A dyed fabric was obtained.
  • resorcinol bis(2,6-dixylenyl phosphate) having an average particle size of 0.6 ⁇ m represented by the formula (VIII) was used instead of the flame retardant represented by (VII).
  • Example 1 instead of the red disperse dye represented by formula (I), a red disperse dye 3.0% owf having an average particle size of 0.8 ⁇ m represented by formula (III) was used, and the formula A dyed fabric was obtained in the same manner except that the flame retardant represented by (VII) was replaced with 2-phenoxyethyldiphenyl phosphate represented by the formula (X) having an average particle size of 0.6 ⁇ m.
  • the flame retardant represented by (VII) was replaced with 2-phenoxyethyldiphenyl phosphate represented by the formula (X) having an average particle size of 0.6 ⁇ m.
  • Example 1 instead of the red disperse dye represented by formula (I), a red disperse dye 3.0% owf having an average particle size of 0.8 ⁇ m represented by formula (III) was used, and the formula 5,5-dimethyl-2-(2′-phenylphenoxy)-1,3,2 with an average particle size of 0.6 ⁇ m represented by the formula (XI) instead of the flame retardant represented by (VII) - A dyed fabric was obtained in the same manner, except that dioxaphosphorinane-2-oxide was used.
  • Comparative example 35 In Example 1, instead of the red disperse dye represented by formula (I), 3.0% owf of red disperse dye having an average particle size of 0.8 ⁇ m represented by formula (IV) was used, and the formula 10-benzyl-9,10-dihydro-9-oxa-10-phosphaphenanthrene having an average particle size of 0.6 ⁇ m represented by the formula (IX) instead of the flame retardant represented by (VII) A dyed fabric was obtained in the same manner except that -10-oxide was used.
  • red disperse dye represented by formula (I) 3.0% owf of red disperse dye having an average particle size of 0.8 ⁇ m represented by formula (IV) was used, and the formula 10-benzyl-9,10-dihydro-9-oxa-10-phosphaphenanthrene having an average particle size of 0.6 ⁇ m represented by the formula (IX) instead of the flame retardant represented by (VII)
  • a dyed fabric was obtained in the same manner except that -10-oxid
  • Comparative example 36 In Example 1, instead of the red disperse dye represented by formula (I), 3.0% owf of red disperse dye having an average particle size of 0.8 ⁇ m represented by formula (IV) was used, and the formula 5,5-dimethyl-2-(2′-phenylphenoxy)-1,3,2 with an average particle size of 0.6 ⁇ m represented by the formula (XI) instead of the flame retardant represented by (VII) - A dyed fabric was obtained in the same manner, except that dioxaphosphorinane-2-oxide was used.
  • Table 1 shows 0.3% of any of the quinone red disperse dyes represented by the formulas (I) to (V) in the presence of 4.0% of the flame retardant represented by the formula (VII). Even when used in the amount of wf, when the treated fabric made of polyester fiber is dyed, both the color difference ⁇ E (100 ° C.) and ⁇ E (130 ° C.) are small and appropriate, and the dyeing speed change rate is also appropriate. indicates that
  • the fabric to be treated with the quinone red disperse dye represented by the formulas (I) to (V), respectively. and the dyed fabric obtained by dyeing the treated fabric with the quinone red disperse dye in the presence of the flame retardant is small, and the dyeing speed described above is small. Since the rate of change is appropriate, even if the flame retardant is used in combination with the quinone red disperse dye, compared to the case of dyeing using the quinone red disperse dye in the absence of the flame retardant, dyeing It can be said that the speed change rate is small.
  • Table 2 shows the quinone red disperse dyes represented by the formulas (I) to (V) in the presence of 4.0% of the flame retardant represented by the formula (VII) at 100 ° C. and 130 ° C. 3.0% wf amount, the obtained dyed product has both small color difference ⁇ E (100°C) and ⁇ E (130°C) and is appropriate, and the rate of change in dyeing speed is also appropriate. indicates that
  • Table 3 shows the quinone red disperse dyes represented by the formulas (I) to (V) in the presence of 8.0% of the flame retardant represented by the formula (VII) at 100 ° C. and 130 ° C. 0.3% wf amount, the resulting dyed product has both small color difference ⁇ E (100° C.) and ⁇ E (130° C.) and is appropriate, and the rate of change in dyeing speed is also appropriate. indicates that
  • Table 4 shows the quinone red disperse dyes represented by the formulas (I) to (V) in the presence of 1.0% of the flame retardant represented by the formula (VII) at 100 ° C. and 130 ° C. 0.3% wf amount, the resulting dyed product has both small color difference ⁇ E (100° C.) and ⁇ E (130° C.) and is appropriate, and the rate of change in dyeing speed is also appropriate. indicates that
  • Table 5 shows the quinone red disperse dyes represented by the formulas (I) to (V) in the presence of 4.0% of the flame retardant represented by the formula (VII) at 100 ° C. and 130 ° C. and 0.3% of the azo red disperse dye represented by the above formula (VI), the resulting dyed product has a color difference ⁇ E (100°C ) and ⁇ E (130° C.) are both small and appropriate, and the dyeing speed change rate is also appropriate.
  • At least one selected from the quinone red disperse dyes represented by the formulas (I) to (V), or the quinones represented by the formulas (I) to (V) Polyester fiber in a processing bath containing at least one selected from red disperse dyes, the azo red disperse dye represented by the formula (VI), and the flame retardant phosphate ester amide represented by the formula (VII)
  • the dyeing simultaneous flame retardant treatment method in which the product is immersed and heated, at temperatures of 100 ° C.
  • Table 6 shows the existence of conventionally known representative flame retardants represented by the formulas (VIII) to (XIII) instead of the flame retardant represented by the formula (VII).
  • the quinone-based red disperse dye represented by the formula (I) the results of dyeing polyester-based textiles are shown. At least one of the dyeing speed change rate was unsuitable, but in Comparative Example 6, all of the color difference ⁇ E (100° C.), ⁇ E (130° C.) and the dyeing speed change rate were proper. Another result of Comparative Example 6 will be shown later.
  • Table 7 shows, in Comparative Examples 7 to 12, instead of the flame retardant represented by the formula (VII), typical conventionally known representatives represented by the formulas (VIII) to (XIII) The results of dyeing polyester textiles with each of the quinone red disperse dyes represented by the formula (II) in the presence of a flame retardant are shown.
  • Comparative Examples 8 to 12 At least one of color difference ⁇ E (100°C) and dyeing speed change rate was unsuitable, but in Comparative Example 7, color difference ⁇ E (100°C) and ⁇ E (130°C) were unsuitable. and dyeing rate change rate were all appropriate. Another result of Comparative Example 7 will be shown later.
  • Table 8 shows, in Comparative Examples 13 to 18, instead of the flame retardant represented by the formula (VII), conventionally known typical flame retardants represented by the formulas (VIII) to (XIII) In the presence of, each of the quinone red disperse dyes represented by the formula (III) is used to show the results when polyester textiles are dyed.
  • Comparative Examples 13, 14, 17 and 18 at least one of the color difference ⁇ E (100°C) and the dyeing speed change rate was unsuitable, but in Comparative Examples 15 and 16, the color difference ⁇ E (100°C) ⁇ E (130° C.) and dyeing rate change were all correct. Other results for Comparative Examples 15 and 16 will be shown later.
  • Table 9 shows typical conventionally known flame retardants represented by the formulas (VIII) to (XIII) instead of the flame retardant represented by the formula (VII) in Comparative Examples 19 to 24.
  • each of the quinone-based red disperse dyes represented by the formula (IV) is used to dye a polyester-based textile product.
  • Comparative Examples 19, 21, 23 and 24 at least one of the color difference ⁇ E (100°C) and the dyeing speed change rate was unsuitable, but in Comparative Examples 20 and 22 the color difference ⁇ E (100°C) ⁇ E (130° C.) and dyeing rate change were all correct. Other results for Comparative Examples 20 and 22 are shown later.
  • Table 10 shows typical conventionally known flame retardants represented by the formulas (VIII) to (XIII) in place of the flame retardant represented by the formula (VII) in Comparative Examples 25 to 30.
  • each of the quinone-based red disperse dyes represented by the formula (V) is used to show the results of dyeing polyester-based textiles.
  • Comparative Example 31 uses a combination of the quinone red disperse dye represented by the formula (I) and the flame retardant represented by the formula (XIII), and Comparative Example 32 is represented by the formula (II).
  • Comparative Example 33 is represented by the quinone red disperse dye represented by the formula (III) and the formula (X).
  • Comparative Example 34 uses a combination of the quinone red disperse dye represented by the formula (III) and the flame retardant represented by the formula (XI), and Comparative Example 35 uses the formula ( IV) and the flame retardant represented by the formula (IX) are used in combination, and Comparative Example 36 uses the quinone red disperse dye represented by the formula (IV) and the above The flame retardants represented by the formula (XI) are used together to show the results of simultaneously dyeing and flame-retarding polyester textiles.
  • the quinone red disperse dye has an average particle size of 0.8 ⁇ m and the amount used is 3.0% wf, and the flame retardant has an average particle size of 0.6 ⁇ m and is used in an amount of 4 .0% owf.
  • Comparative Examples 31-36 the combinations of red disperse dye and flame retardant correspond to those in Comparative Examples 6, 7, 15, 16, 20 and 22 previously described in that order, but the use of red disperse dye While the amount was 0.3% in Comparative Examples 6, 7, 15, 16, 20 and 22, it was 3.0% in Comparative Examples 31 to 36. As a result, At least one of color difference ⁇ E (100° C.), ⁇ E (130° C.) and dyeing speed change rate is unsuitable.
  • the flame retardants represented by the formulas (VIII), (IX), (X), (XI) and (XIII) are, as seen in Comparative Examples 6, 7, 15, 16, 20 and 22,
  • the amount of the red disperse dye used in combination is small (0.3% wf)
  • both the color difference ⁇ E (100°C), ⁇ E (130°C) and the rate of change in the dyeing speed are appropriate.
  • the red disperse dye used in combination is used in a large amount (3.0% wf)

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Abstract

According to the present invention, there is provided a fire retardant and simultaneously dyeing method for polyester-based textiles, the method comprising immersing a polyester-based textile in a processing bath containing a specific quinone red disperse dye and fire retardant phosphoric acid ester amide represented by formula (VII), and heating the textile.　According to this method, it is possible to obtain a dyed fire-retardant polyester-based textile having excellent reproducibility because the change in the dyeing speed of the quinone red disperse dye is small despite the presence of the fire retardant.

Description

ポリエステル系繊維品の染色同時難燃加工方法Method for dyeing and flame retardant treatment of polyester textiles
　本発明はポリエステル系繊維品の染色同時難燃加工方法に関し、詳しくは、特定のキノン系赤色分散染料と特定の難燃剤を含む加工浴にポリエステル系繊維品を浸漬し、加圧下に加熱して、ポリエステル系繊維品を染色同時難燃加工することによって、染色再現性よく、染色難燃加工ポリエステル系繊維品を得ることができる、ポリエステル系繊維品の染色同時難燃加工方法に関する。更に、本発明は、そのようにして得られる染色難燃加工ポリエステル系繊維品に関する。 The present invention relates to a method for dyeing and simultaneously flame-retarding polyester fiber products, and more specifically, immersing a polyester fiber product in a processing bath containing a specific quinone red disperse dye and a specific flame retardant, and heating under pressure. relates to a method for simultaneously dyeing and flame-retarding a polyester fiber product, which can obtain a dyed and flame-retardant polyester fiber product with good dyeing reproducibility by subjecting the polyester fiber product to flame-retardant treatment at the same time as dyeing. Furthermore, the present invention relates to dyed, flame-retardant polyester fiber articles thus obtained.
　ポリエステル系繊維品のような疎水性繊維品の染色には、通常、耐光堅牢度にすぐれるキノン系分散染料が用いられているが、なかでも、下記式（Ｉ） Quinon-based disperse dyes, which have excellent light fastness, are usually used for dyeing hydrophobic textiles such as polyester textiles. Among them, the following formula (I)
Figure JPOXMLDOC01-appb-C000014
  
で表されるキノン系赤色分散染料は、特定の黄色分散染料と組み合わせることによって、より高度の耐光堅牢度を有する分散染料組成物を与えることが知られている（例えば、特許文献１参照）。
Figure JPOXMLDOC01-appb-C000014
The quinone-based red disperse dye represented by is known to give a disperse dye composition having a higher degree of light fastness by combining with a specific yellow disperse dye (see, for example, Patent Document 1).
　また、下記式（ＩＩ） Also, the following formula (II)
Figure JPOXMLDOC01-appb-C000015
  
で表されるキノン系赤色分散染料は、従来、耐光堅牢度にすぐれる染色物を与えることが知られている分散染料である（特許文献２参照）。
Figure JPOXMLDOC01-appb-C000015
The quinone-based red disperse dye represented by is conventionally known to give a dyed product with excellent light fastness (see Patent Document 2).
　下記式（ＩＩＩ） Formula (III) below
Figure JPOXMLDOC01-appb-C000016
  
、
Figure JPOXMLDOC01-appb-C000016
,
下記式（ＩＶ） Formula (IV) below
Figure JPOXMLDOC01-appb-C000017
  
、及び
Figure JPOXMLDOC01-appb-C000017
,as well as
下記式（Ｖ） Formula (V) below
Figure JPOXMLDOC01-appb-C000018
  
Figure JPOXMLDOC01-appb-C000018
  
で表されるキノン系赤色分散染料も、これらを特定のキノフタロン系分散染料と組み合わせることによって、耐光堅牢度が改善された分散染料組成物を与えることも知られている（例えば、特許文献３参照）。 The quinone-based red disperse dye represented by is also known to give a disperse dye composition with improved light fastness by combining these with a specific quinophthalone-based disperse dye (see, for example, Patent Document 3) ).
　一方、アゾ系分散染料は、一般に、耐光堅牢度はキノン系分散染料よりも劣るが、着色力が強いことが知られている。 On the other hand, azo disperse dyes are generally known to be inferior to quinone disperse dyes in light fastness, but to have strong coloring power.
　下記式（ＶＩ） The following formula (VI)
Figure JPOXMLDOC01-appb-C000019
  
Figure JPOXMLDOC01-appb-C000019
  
で表されるアゾ系赤色分散染料は、これを構造の異なる他のアゾ系赤色分散染料と組み合わせることによって、各種の堅牢度にすぐれる染色物を与えることが知られている（例えば、特許文献４参照）。 The azo red disperse dye represented by is known to give various dyes with excellent fastness by combining it with other azo red disperse dyes having different structures (for example, patent documents 4).
　そして、従来、ポリエステル系繊維品を染色する場合、求める色調に応じて、赤色、黄色及び青色の分散染料を三原色として用いて、これらの混色によるのが一般的である。このような場合、これら赤色、黄色及び青色の分散染料の染色特性、特に、染色速度、即ち、染色時の温度上昇に伴う染着量の増加率が揃っているときは、染色条件、例えば、染色温度がある程度、変動しても、得られる染色物が色調において受ける影響は少ない。即ち、上記染色速度が揃っている三原色の分散染料は、ポリエステル系繊維品の染色の再現性にすぐれている。 Conventionally, when dyeing polyester textiles, it is common to use red, yellow and blue disperse dyes as the three primary colors according to the desired color tone, and to mix these colors. In such a case, when the dyeing characteristics of these red, yellow and blue disperse dyes, particularly the dyeing speed, that is, the rate of increase in the amount of dyeing accompanying the temperature rise during dyeing, are uniform, the dyeing conditions, such as Even if the dyeing temperature fluctuates to a certain extent, the resulting dyed goods have little effect on the shade. That is, the disperse dyes of the three primary colors with uniform dyeing speeds are excellent in reproducibility of dyeing of polyester fiber products.
　反対に、赤色、黄色及び青色の三原色の分散染料の染色速度が揃っていないときは、染色条件の僅かな変動によっても、得られる染色物の色調のみならず、色濃度も大幅に変化する。 On the contrary, when the dyeing speeds of the disperse dyes of the three primary colors of red, yellow and blue are not uniform, not only the color tone of the dyed material obtained but also the color density will change significantly even with a slight change in the dyeing conditions.
　かくして、ポリエステル系繊維品を分散染料にて染色する場合、赤色、黄色及び青色の三原色の分散染料の染色速度が揃っていることが求められる。そこで、染色再現性よく、ポリエステル系繊維品を染色するために、赤色、黄色及び青色の三原色の分散染料について、それぞれ特定の構造を有する染料の組み合わせを用いることが提案されている（例えば、特許文献５及び６参照）。 Thus, when polyester textiles are dyed with disperse dyes, it is required that the disperse dyes of the three primary colors of red, yellow and blue have uniform dyeing speeds. Therefore, in order to dye polyester textiles with good dyeing reproducibility, it has been proposed to use a combination of three primary color disperse dyes of red, yellow and blue, each having a specific structure (for example, patent References 5 and 6).
　上述したポリエステル系繊維品の染色におけると同様に、キノン系赤色分散染料と共に難燃剤を含む加工浴にポリエステル系繊維品を浸漬し、加熱して、ポリエステル系繊維品を染色すると同時に、難燃剤によって難燃加工を施す場合においても、用いる難燃剤によっては、同じ条件下に染色しても、難燃剤の不存在下にキノン系赤色分散染料にてポリエステル系繊維品を染色する場合に比較して、上記赤色分散染料の染色速度が変動し、得られる染色物における色調や色濃度が大幅に変化する結果、染色再現性よく、ポリエステル系繊維品を染色同時難燃加工することができないことがある。 As in the dyeing of the polyester textiles described above, the polyester textiles are immersed in a processing bath containing a flame retardant together with a quinone red disperse dye and heated to dye the polyester textiles, and at the same time, the flame retardant Even when performing flame retardant processing, depending on the flame retardant used, even if dyeing is performed under the same conditions, compared to dyeing polyester textiles with a quinone red disperse dye in the absence of a flame retardant. As a result, the dyeing speed of the red disperse dye fluctuates, and the color tone and color density of the resulting dyed product change significantly. .
　従って、キノン系赤色分散染料を用いて、ポリエステル系繊維品を染色すると同時に難燃加工して、染色再現性よく、難燃加工染色物を得るには、用いるキノン系赤色分散染料が染色再現性にすぐれるのみならず、用いる難燃剤もまた、併用するキノン系赤色分散染料のすぐれた染色再現性を阻害するものであってはならない。 Therefore, using a quinone red disperse dye to dye a polyester fiber product and simultaneously flame retarding it to obtain a flame retardant dyed product with good dyeing reproducibility, the quinone red disperse dye used has a good dyeing reproducibility. The flame retardant to be used must not only be excellent in color reproducibility, but must also not interfere with the excellent dyeing reproducibility of the quinone red disperse dye used in combination.
ＷＯ２０１２／０７３６９６Ａ１WO2012/073696A1 特開平９－１７６５０９Japanese Patent Laid-Open No. 9-176509 特開昭５９－５１９５０Japanese Patent Laid-Open No. 59-51950 特開平１０－７７５８３Japanese Patent Laid-Open No. 10-77583 特開２００４－１６８９５０JP 2004-168950 ＷＯ２０１２／０６７０２７Ａ１WO2012/067027A1
　本発明は、キノン系赤色分散染料と共に難燃剤を含む加工浴中にてポリエステル系繊維品を染色同時難燃加工する場合において、前記式（Ｉ）～（Ｖ）で表されるキノン系赤色分散染料から選ばれる少なくとも１種、又は前記式（Ｉ）～（Ｖ）で表されるキノン系赤色分散染料から選ばれる少なくとも１種と前記式（ＶＩ）で表されるアゾ系赤色分散染料を用いると共に、特定の難燃剤を用いることによって、染色再現性よく、染色難燃加工ポリエステル系繊維品を得るポリエステル系繊維品の染色同時難燃加工方法を提供することを目的とする。 The present invention provides the quinone red dispersant represented by the above formulas (I) to (V) when simultaneously dyeing and flame retarding polyester textiles in a processing bath containing a flame retardant together with a quinone red disperse dye. At least one selected from dyes, or at least one selected from quinone red disperse dyes represented by formulas (I) to (V) and an azo red disperse dye represented by formula (VI) are used. Another object of the present invention is to provide a method for simultaneously dyeing and flame-retarding polyester textiles, which yields dyed flame-retardant polyester textiles with good dyeing reproducibility by using a specific flame retardant.
　更に、本発明によれば、上記染色同時難燃加工方法によって得られた染色難燃加工ポリエステル系繊維品を提供することを目的とする。 Furthermore, according to the present invention, it is an object to provide a dyed flame-retardant polyester fiber product obtained by the method for flame-retardant treatment at the same time as dyeing.
　本発明によれば、
（Ａ）（１）下記式（Ｉ） According to the invention,
(A) (1) Formula (I) below
Figure JPOXMLDOC01-appb-C000020
  
Figure JPOXMLDOC01-appb-C000020
  
で表されるキノン系赤色分散染料、
（２）下記式（ＩＩ） A quinone-based red disperse dye represented by
(2) Formula (II) below
Figure JPOXMLDOC01-appb-C000021
  
Figure JPOXMLDOC01-appb-C000021
  
で表されるキノン系赤色分散染料、
（３）下記式（ＩＩＩ） A quinone-based red disperse dye represented by
(3) the following formula (III)
Figure JPOXMLDOC01-appb-C000022
  
Figure JPOXMLDOC01-appb-C000022
  
で表されるキノン系赤色分散染料、
（４）下記式（ＩＶ） A quinone-based red disperse dye represented by
(4) Formula (IV) below
Figure JPOXMLDOC01-appb-C000023
  
Figure JPOXMLDOC01-appb-C000023
  
で表されるキノン系赤色分散染料、及び
（５）下記式（Ｖ） and (5) a quinone-based red disperse dye represented by the following formula (V)
Figure JPOXMLDOC01-appb-C000024
  
Figure JPOXMLDOC01-appb-C000024
  
で表されるキノン系赤色分散染料よりなる群から選ばれる少なくとも１種と、
（Ｂ）下記式（ＶＩＩ） At least one selected from the group consisting of quinone-based red disperse dyes represented by
(B) Formula (VII) below
Figure JPOXMLDOC01-appb-C000025
  
Figure JPOXMLDOC01-appb-C000025
  
で表されるリン酸エステルアミドを含む加工浴中にポリエステル系繊維品を浸漬し、加熱するポリエステル系繊維品の染色同時難燃加工方法が提供される。 Provided is a method for simultaneously dyeing and flame-retarding a polyester fiber article, comprising immersing the polyester fiber article in a processing bath containing a phosphoric acid ester amide represented by and heating the polyester fiber article.
　以下、本発明において、上記方法を第１の方法ということがある。 Hereinafter, in the present invention, the above method may be referred to as the first method.
　更に、本発明によれば、上記式（Ｉ）～（Ｖ）で表されるキノン系赤色分散染料よりなる群から選ばれる少なくとも１種と式（ＶＩ） Furthermore, according to the present invention, at least one selected from the group consisting of the quinone-based red disperse dyes represented by the above formulas (I) to (V) and the formula (VI)
Figure JPOXMLDOC01-appb-C000026
  
Figure JPOXMLDOC01-appb-C000026
  
で表されるアゾ系赤色分散染料と、上記式（ＶＩＩ）で表されるリン酸エステルアミドを含む加工浴中にポリエステル系繊維品を浸漬し、加熱するポリエステル系繊維品の染色同時難燃加工方法が提供される。 and the azo red disperse dye represented by and the polyester fiber product is immersed in a processing bath containing the phosphoric acid ester amide represented by the above formula (VII), and the polyester fiber product is dyed and simultaneously flame retarded. A method is provided.
　以下、本発明において、上記方法を第２の方法ということがある。 Hereinafter, in the present invention, the above method may be referred to as the second method.
　本発明による上述した第１の方法においては、詳しくは、上記加工浴中にポリエステル系繊維品を浸漬し、１０５℃以上に加熱し、また、上記加工浴は、好ましくは、用いるキノン系赤色分散染料を濃度０．０５～５％оｗｆの範囲で有し、上記リン酸エステルアミドを濃度０．５～１０％оｗｆの範囲で有する。 Specifically, in the above-described first method according to the present invention, the polyester fiber product is immersed in the processing bath and heated to 105° C. or higher, and the processing bath preferably contains the quinone red dispersion to be used. It contains a dye in a concentration range of 0.05 to 5% owf, and the phosphate ester amide in a concentration range of 0.5 to 10% owf.
　本発明による上述した第２の方法においては、詳しくは、上記加工浴中にポリエステル系繊維品を浸漬し、１０５℃以上に加熱し、また、上記加工浴は、好ましくは、用いるキノン系赤色分散染料とアゾ系赤色分散染料を合計濃度０．０５～５％оｗｆの範囲で有し、上記リン酸エステルアミドを濃度０．５～１０％оｗｆの範囲で有する。 Specifically, in the second method according to the present invention, the polyester fiber product is immersed in the processing bath and heated to 105° C. or higher. The total concentration of the dye and the azo red disperse dye is in the range of 0.05 to 5% wf, and the phosphate ester amide is in the concentration range of 0.5 to 10% wf.
　また、本発明による上述した第１と第２の方法においては、用いる赤色分散染料は、キノン系、アゾ系赤色分散染料を問わず、いずれも、そして、リン酸エステルアミドはいずれも、平均粒子径０．２～２．０μｍの範囲にあるものであることが好ましい。 In the above-described first and second methods according to the present invention, the red disperse dye to be used, regardless of whether it is a quinone-based or azo-based red disperse dye, and both of the phosphoric acid ester amides have an average particle size of It is preferable that the diameter is in the range of 0.2 to 2.0 μm.
　更に、本発明によれば、上記赤色分散染料と上記難燃剤リン酸エステルアミドを含む染色難燃加工ポリエステル系繊維品が提供される。 Furthermore, according to the present invention, there is provided a dyed flame-retardant polyester fiber product containing the red disperse dye and the flame retardant phosphate ester amide.
　本発明によるポリエステル系繊維品の染色同時難燃加工方法は、前記式（ＶＩＩ）で表される難燃剤リン酸エステルアミドと共に、
　前記式（Ｉ）～（Ｖ）で表されるキノン系赤色分散染料よりなる群から選ばれる少なくとも１種か、又は
　前記式（Ｉ）～（Ｖ）で表されるキノン系赤色分散染料よりなる群から選ばれる少なくとも１種と前記式（ＶＩ）で表されるアゾ系赤色分散染料
を用いて、ポリエステル系繊維品を染色すると同時に難燃加工するものである。 The dyeing and simultaneous flame retardant processing method for polyester fiber products according to the present invention includes, together with the flame retardant phosphate ester amide represented by the formula (VII),
At least one selected from the group consisting of the quinone red disperse dyes represented by the formulas (I) to (V), or consisting of the quinone red disperse dyes represented by the formulas (I) to (V) Using at least one selected from the group and the azo red disperse dye represented by the formula (VI), a polyester fiber product is dyed and at the same time subjected to flame retardant treatment.
　従来、知られている難燃剤とキノン系赤色分散染料を含む加工浴にてポリエステル系繊維品を染色同時難燃加工した場合、上記難燃剤の不存在下に上記赤色分散染料にて染色した場合と比較して、通常、上記赤色分散染料は、その染色速度が大きく変化するために、染色再現性よく染色難燃加工ポリエステル系繊維品を得ることができない。 Conventionally, when a polyester fiber product is dyed and simultaneously flame retarded in a processing bath containing a known flame retardant and a quinone red disperse dye, when dyeing with the above red disperse dye in the absence of the above flame retardant Compared with red disperse dyes, the dyeing speed of the red disperse dyes generally varies greatly, so that it is not possible to obtain flame-retardant polyester textiles with good dyeing reproducibility.
　しかしながら、本発明に従って、前記式（ＶＩＩ）で表される難燃剤リン酸エステルアミドと共に、前記式（Ｉ）から（Ｖ）で表されるキノン系赤色分散染料の少なくとも１種、又は前記式（Ｉ）から（Ｖ）で表されるキノン系赤色分散染料の少なくとも１種と上記式（ＶＩ）で表されるアゾ系赤色分散染料を含む加工浴中にてポリエステル系繊維品を染色同時難燃加工した場合、上記赤色分散染料の染色速度の変化がいずれも、小さいことから、染色再現性よく、染色難燃加工ポリエステル系繊維品を得ることができる。 However, according to the present invention, together with the flame retardant phosphate amide of formula (VII), at least one of the quinone red disperse dyes of formulas (I) to (V), or Dyeing and simultaneously flame retarding a polyester fiber product in a processing bath containing at least one of the quinone red disperse dyes represented by I) to (V) and the azo red disperse dye represented by the above formula (VI) When processed, the dyeing rate of the red disperse dye is small, so that the dyed flame-retardant polyester fiber product can be obtained with good dyeing reproducibility.
　本発明によるポリエステル系繊維品の染色同時難燃加工方法は、前記式（Ｉ）から（Ｖ）で表されるキノン系赤色分散染料の少なくとも１種か、又は前記式（Ｉ）から（Ｖ）で表されるキノン系赤色分散染料の少なくとも１種と前記式（ＶＩ）で表されるアゾ系赤色分散染料と、前記式（ＶＩＩ）で表されるリン酸エステルアミドを含む加工浴中にポリエステル系繊維品を浸漬し、加熱して、染色同時難燃加工するものであり、このような方法によれば、染色再現性よく、染色難燃加工ポリエステル系繊維品を得ることができる。 The method for dyeing and simultaneously flame-retarding a polyester fiber product according to the present invention is at least one of the quinone red disperse dyes represented by the above formulas (I) to (V), or the above formulas (I) to (V). Polyester in a processing bath containing at least one quinone red disperse dye represented by the formula (VI) and the azo red disperse dye represented by the formula (VI), and a phosphoric acid ester amide represented by the formula (VII) The flame-retardant treatment is carried out at the same time as dyeing by immersing and heating the polyester-based textile product. According to such a method, the dyed flame-retardant polyester-based textile product can be obtained with good dyeing reproducibility.
　即ち、本発明によるポリエステル系繊維品の染色同時難燃加工方法は、その加工浴に前記式（Ｉ）から（Ｖ）で表されるキノン系赤色分散染料の少なくとも１種か、又は前記式（Ｉ）から（Ｖ）で表されるキノン系赤色分散染料の少なくとも１種と前記式（ＶＩ）で表されるアゾ系赤色分散染料と共に、前記式（ＶＩＩ）で表されるリン酸エステルアミドを含む。 That is, in the method for simultaneously dyeing and flame-retarding a polyester fiber product according to the present invention, at least one of the quinone red disperse dyes represented by the above formulas (I) to (V) or the above formula ( At least one of the quinone red disperse dyes represented by I) to (V) and the azo red disperse dye represented by the formula (VI) together with the phosphate ester amide represented by the formula (VII) include.
　前記式（Ｉ）から（Ｖ）で表されるキノン系赤色分散染料と前記式（ＶＩ）で表されるアゾ系赤色分散染料はいずれも既に知られており、本発明の方法においては、いずれも市販品を用いることができる。 Both the quinone red disperse dyes represented by the above formulas (I) to (V) and the azo red disperse dyes represented by the above formula (VI) are already known. A commercially available product can also be used.
　上記式（Ｉ）で表されるキノン系赤色分散染料は、Ｃ．Ｉ．Ｄｉｓｐｅｒｓｅ　Ｒｅｄ　８６である。 The quinone-based red disperse dye represented by the above formula (I) is C.I. I. Disperse Red 86.
　上記式（ＩＩ）で表されるキノン系赤色分散染料は、Ｃ．Ｉ．Ｄｉｓｐｅｒｓｅ　Ｒｅｄ　１９１であり、上記式（ＩＩＩ）で表されるキノン系赤色分散染料は、Ｃ．Ｉ．Ｄｉｓｐｅｒｓｅ　Ｒｅｄ　９２であり、上記式（ＩＶ）で表されるキノン系赤色分散染料は、Ｃ．Ｉ．Ｄｉｓｐｅｒｓｅ　Ｒｅｄ　５３であり、上記式（Ｖ）で表されるキノン系赤色分散染料は、Ｃ．Ｉ．Ｄｉｓｐｅｒｓｅ　Ｒｅｄ　６０である。上記式（ＶＩ）で表されるアゾ系赤色分散染料は、Ｃ．Ｉ．Ｄｉｓｐｅｒｓｅ　Ｒｅｄ　１６７：１である。 The quinone-based red disperse dye represented by the formula (II) is C.I. I. Disperse Red 191, and the quinone-based red disperse dye represented by the above formula (III) is C.I. I. Disperse Red 92, and the quinone-based red disperse dye represented by the above formula (IV) is C.I. I. Disperse Red 53, the quinone-based red disperse dye represented by the above formula (V), is C.I. I. Disperse Red 60. The azo red disperse dye represented by the formula (VI) is C.I. I. Disperse Red 167:1.
　本発明においては、上記キノン系赤色分散染料か、又は上記キノン系赤色分散染料とアゾ系赤色分散染料と共に、前記難燃剤リン酸エステルアミドを用いて、ポリエステル系繊維品に染色同時難燃加工を施すに際して、上記赤色分散染料と難燃剤リン酸エステルアミドがポリエステル系繊維品の内部に十分に拡散し、付着するように、上記赤色分散染料と難燃剤リン酸エステルアミドはいずれも、０．２～２．０μｍの平均粒子径を有するものであることが好ましい。但し、上記赤色分散染料と難燃剤リン酸エステルアミドが同じ平均粒子径を有する必要はない。 In the present invention, the quinone-based red disperse dye, or the quinone-based red disperse dye and the azo-based red disperse dye, and the flame retardant phosphate ester amide are used to perform dyeing and simultaneous flame retardancy on the polyester fiber product. At the time of application, both the red disperse dye and the flame retardant phosphate ester amide are 0.2 It preferably has an average particle size of ~2.0 µm. However, the red disperse dye and the flame retardant phosphate ester amide need not have the same average particle size.
　上述した範囲の平均粒子径を有する赤色分散染料とリン酸エステルアミドは、例えば、上記赤色分散染料とリン酸エステルアミドをそれぞれ、予め、界面活性剤を含む水中でサンドミルやボールミルで微細化することによって得ることができる。 The red disperse dye and the phosphate ester amide having an average particle size within the range described above can be obtained, for example, by pulverizing the red disperse dye and the phosphate ester amide in advance with a sand mill or a ball mill in water containing a surfactant. can be obtained by
　前記赤色分散染料を微細化する際に用いる界面活性剤としては、例えば、ナフタリンスルホン酸とアルキルベンゼンスルホン酸のホルマリン縮合物、ナフタレンスルホン酸のホルマリン縮合物、クレゾールと２－ナフトール－６－スルホン酸のホルマリン縮合物、アルキルナフタレンスルホン酸のホルマリン縮合物、クレオソート油スルホン酸のホルマリン縮合物、リグニンスルホン酸等のアニオン界面活性剤、エチレンオキサイドとプロピレンオキサイドのブロック共重合物、アルキルフェノールのエチレンオキサイド付加物、ポリスチレン化フェノールのエチレンオキサイド付加物等のノニオン界面活性剤や、これらのアニオン界面活性剤とノニオン界面活性剤との混合物が好ましい。 Examples of surfactants used for refining the red disperse dye include formalin condensates of naphthalenesulfonic acid and alkylbenzenesulfonic acid, formalin condensates of naphthalenesulfonic acid, and cresol and 2-naphthol-6-sulfonic acid. Formalin condensates, formalin condensates of alkylnaphthalene sulfonic acid, formalin condensates of creosote oil sulfonic acid, anionic surfactants such as lignin sulfonic acid, block copolymers of ethylene oxide and propylene oxide, ethylene oxide adducts of alkylphenols Nonionic surfactants such as ethylene oxide adducts of polystyrenated phenols, and mixtures of these anionic surfactants and nonionic surfactants are preferred.
　前記リン酸エステルアミドを微細化する際に用いる界面活性剤としては、例えば、アリール化フェノールエチレンオキサイド付加物の硫酸エステル塩、スチレン化フェノールエチレンオキサイド付加物のスルホ琥珀酸エステル塩等のアニオン界面活性剤、エチレンオキサイドとプロピレンオキサイドのブロック共重合物、アルキルフェノールのエチレンオキサイド付加物、ポリスチレン化フェノールのエチレンオキサイド付加物等のノニオン界面活性剤、又は、これらのアニオン界面活性剤とノニオン界面活性剤との混合物が好ましい。 Examples of surfactants used for refining the phosphoric acid ester amide include anionic surfactants such as sulfuric acid ester salts of arylated phenol ethylene oxide adducts and sulfosuccinic acid ester salts of styrenated phenol ethylene oxide adducts. nonionic surfactants such as agents, block copolymers of ethylene oxide and propylene oxide, ethylene oxide adducts of alkylphenols, ethylene oxide adducts of polystyrenated phenols, or combinations of these anionic surfactants and nonionic surfactants Mixtures are preferred.
　本発明によるポリエステル系繊維品の染色同時難燃加工方法は、上述したように、特定の赤色分散染料と特定の難燃剤をそれぞれ上記界面活性剤の存在下に湿式粉砕して、それぞれ上記赤色分散染料及び難燃剤の微粒子を含む分散液とし、これらを水を含む浴に加えて、所定の浴比を有する加工浴を構成し、この加工浴にポリエステル系繊維品を浸漬し、加圧下に１０５℃以上、好ましくは、１０５～１４０℃の範囲の温度、特に好ましくは、１１０～１４０℃の範囲の温度で３０～６０分間、浴中吸尽処理し、この後、このように処理したポリエステル系繊維品を加工浴から取り出し、ソーピング処理、水洗処理した後、脱水乾燥すれば、染色難燃加工したポリエステル系繊維品を得ることができる。 In the method for dyeing and simultaneously flame-retarding polyester fiber products according to the present invention, as described above, a specific red disperse dye and a specific flame retardant are wet pulverized in the presence of the surfactant, and the red dispersion A dispersion liquid containing fine particles of a dye and a flame retardant is added to a bath containing water to form a processing bath having a predetermined bath ratio. ° C. or higher, preferably in the range from 105 to 140 ° C., particularly preferably at a temperature in the range from 110 to 140 ° C., for 30 to 60 minutes in a bath exhaust treatment, after which the polyester system thus treated The fiber product is removed from the processing bath, soaped, washed with water, dehydrated and dried to obtain a dyed flame-retardant polyester fiber product.
　本発明において、例えば、液流染色機を用いて、染色機内の加工浴にポリエステル系繊維品を浸漬し、１０５℃以上に加熱して、浴中吸尽処理する際、通常、染色機内の圧力は、０．１～０．５ＭＰａの範囲である。 In the present invention, for example, using a liquid jet dyeing machine, the polyester fiber product is immersed in the processing bath in the dyeing machine, heated to 105 ° C. or higher, and exhausted in the bath. is in the range of 0.1-0.5 MPa.
　このようにして、本発明によれば、上記赤色分散染料にて染色されていると共に、上記難燃剤にて難燃加工されているポリエステル系繊維品を得ることができる。 Thus, according to the present invention, a polyester fiber product dyed with the red disperse dye and flame-retardant-treated with the flame retardant can be obtained.
　本発明による第１の方法において、前記キノン系赤色分散染料と難燃剤リン酸エステルアミドの使用量は、特に限定されるものではないが、キノン系赤色分散染料の使用量は、通常、０．０５～５％ｏｗｆの範囲であり、好ましくは、０．１～５％ｏｗｆの範囲であり、更に好ましくは、０．３～３．０％ｏｗｆの範囲である。難燃剤リン酸エステルアミドの使用量は、通常、染色するポリエステル系繊維品に十分な難燃性能を付与するために、０．５～１０％ｏｗｆの範囲であることが好ましく、０．５～８．０％ｏｗｆの範囲であることがより好ましく、１．０～８．０％ｏｗｆの範囲であることが最も好ましい。 In the first method according to the present invention, the amounts of the quinone red disperse dye and the flame retardant phosphate ester amide used are not particularly limited, but the amount of the quinone red disperse dye used is usually 0.5. It is in the range of 05 to 5%owf, preferably in the range of 0.1 to 5%owf, more preferably in the range of 0.3 to 3.0%owf. The amount of the flame retardant phosphate ester amide used is preferably in the range of 0.5 to 10% owf in order to impart sufficient flame retardancy to the dyed polyester fiber product, and 0.5 to A range of 8.0% owf is more preferred, and a range of 1.0 to 8.0% owf is most preferred.
　本発明による第２の方法においては、前記キノン系赤色分散染料と前記アゾ系赤色分散染料と難燃剤リン酸エステルアミドの使用量は、特に限定されるものではないが、前記キノン系赤色分散染料と前記アゾ系赤色分散染料の使用量は、合計量にて、通常、０．０５～５％ｏｗｆの範囲であり、好ましくは、０．１～５％ｏｗｆの範囲であり、更に好ましくは、０．３～３．０％ｏｗｆの範囲である。難燃剤リン酸エステルアミドの使用量は、上記と同じである。 In the second method according to the present invention, the amounts of the quinone red disperse dye, the azo red disperse dye and the flame retardant phosphate ester amide are not particularly limited, but the quinone red disperse dye And the amount of the azo red disperse dye used, in total amount, is usually in the range of 0.05 to 5% owf, preferably in the range of 0.1 to 5% owf, more preferably It ranges from 0.3 to 3.0%owf. The amount of the flame retardant phosphate ester amide used is the same as above.
　また、加工浴の浴比は、特に制限されるものではないが、通常、１：３～１：３０の範囲であり、好ましくは、１：５～１：２０の範囲である。浴比が１：３よりも低い場合は、ポリエステル系繊維品が加工浴に十分に浸漬されないために染色むらが発生するおそれがあり、他方、１：３０よりも高い場合は、染色同時難燃加工に用いる水量が徒に多くなるので不経済である。 Also, the bath ratio of the working bath is not particularly limited, but is usually in the range of 1:3 to 1:30, preferably in the range of 1:5 to 1:20. If the bath ratio is lower than 1:3, uneven dyeing may occur because the polyester fiber product is not sufficiently immersed in the processing bath. It is uneconomical because the amount of water used for processing is unnecessarily large.
　本発明によるポリエステル系繊維品の染色同時難燃加工方法において、ポリエステル系繊維品とは、少なくともポリエステル繊維を含む繊維と、そのような繊維を含む糸、綿、編織布や不織布等の布帛をいい、好ましくは、ポリエステル繊維、これよりなる糸、綿、編織布や不織布等の布帛をいう。更に、編織布や不織布等の布帛は単層であっても二層以上の積層体であってもよく、糸、綿、編織布や不織布等からなる複合体であってもよい。 In the method of dyeing and simultaneously flame-retarding polyester fiber products according to the present invention, polyester fiber products refer to fibers containing at least polyester fibers, and fabrics such as yarns, cotton, knitted and woven fabrics, and non-woven fabrics containing such fibers. Preferably, it refers to polyester fibers, yarns made from these fibers, cotton, and fabrics such as knitted and woven fabrics and non-woven fabrics. Further, the fabric such as a woven fabric or a non-woven fabric may be a single layer or a laminate of two or more layers, or may be a composite made of yarn, cotton, a woven fabric, a non-woven fabric, or the like.
　本発明において、上記ポリエステル繊維は、例えば、ポリエチレンテレフタレート、ポリプロピレンテレフタレート、ポリブチレンテレフタレート、ポリエチレンナフタレート、ポリブチレンナフタレート、ポリエチレンテレフタレート／イソフタレート、ポリエチレンテレフタレート／５－スルホイソフタレート、ポリエチレンテレフタレート／ポリオキシベンゾイル、ポリブチレンテレフタレート／イソフタレート、ポリ（Ｄ－乳酸）、ポリ（Ｌ－乳酸）、Ｄ－乳酸とＬ－乳酸の共重合体、Ｄ－乳酸と脂肪族ヒドロキシカルボン酸との共重合体、Ｌ－乳酸と脂肪族ヒドロキシカルボン酸との共重合体、ポリ－ε－カプロラクトン（ＰＣＬ）等のポリカプロラクトン、ポリリンゴ酸、ポリヒドロキシカルボン酪酸、ポリヒドロキシ吉草酸、β－ヒドロキシ酪酸（３ＨＢ）－３－ヒドロキシ吉草酸（３ＨＶ）ランダム共重合体等のポリ脂肪族ヒドロキシカルボン酸、ポリエチレンサクシネート（ＰＥＳ）、ポリブチレンサクシネート（ＰＢＳ）、ポリブチレンアジペート、ポリブチレンサクシネート－アジペート共重合体等のグリコールと脂肪族ジカルボン酸とのポリエステル等を挙げることができるが、これら例示されたものに限定されない。 In the present invention, the polyester fiber is, for example, polyethylene terephthalate, polypropylene terephthalate, polybutylene terephthalate, polyethylene naphthalate, polybutylene naphthalate, polyethylene terephthalate/isophthalate, polyethylene terephthalate/5-sulfoisophthalate, polyethylene terephthalate/polyoxy benzoyl, polybutylene terephthalate/isophthalate, poly(D-lactic acid), poly(L-lactic acid), copolymers of D-lactic acid and L-lactic acid, copolymers of D-lactic acid and aliphatic hydroxycarboxylic acids, Copolymers of L-lactic acid and aliphatic hydroxycarboxylic acids, polycaprolactones such as poly-ε-caprolactone (PCL), polymalic acid, polyhydroxycarboxylic butyric acid, polyhydroxyvaleric acid, β-hydroxybutyric acid (3HB)-3 - Polyaliphatic hydroxycarboxylic acids such as hydroxyvaleric acid (3HV) random copolymers, polyethylene succinate (PES), polybutylene succinate (PBS), polybutylene adipate, polybutylene succinate-adipate copolymers, etc. Examples include polyesters of glycol and aliphatic dicarboxylic acid, but are not limited to these examples.
　本発明の方法によって得られる染色難燃加工ポリエステル系繊維品は、例えば、座席シート、シートカバー、カーテン、壁紙、天井クロス、カーペット、緞帳、建築養生シート、テント、帆布等に好適に用いられる。 The dyed flame-retardant polyester fiber product obtained by the method of the present invention is suitably used for, for example, seat sheets, seat covers, curtains, wallpapers, ceiling cloths, carpets, drop curtains, architectural protection sheets, tents, canvases, and the like.
　本発明においては、本発明によるポリエステル系繊維品の染色同時難燃加工方法による染色再現性が阻害されない限り、従来から既に知られているその他の分散染料を併用することができる。そのような分散染料としては、例えば、Ｃ．Ｉ．Ｄｉｓｐｅｒｓｅ　Ｙｅｌｌｏｗ　７１、４２、５１、Ｃ．Ｉ．Ｓｏｌｖｅｎｔ　Ｙｅｌｌｏｗ １６３等の黄色分散染料、Ｃ．Ｉ．Ｄｉｓｐｅｒｓｅ　Ｂｌｕｅ　５４、６０、７７、１６５等の青色分散染料、Ｃ．Ｉ．Ｄｉｓｐｅｒｓｅ　Ｏｒａｎｇｅ　２９、１５５等の橙色分散染料等を挙げることができるが、これらに限定されるものではない。 In the present invention, other conventionally known disperse dyes can be used in combination as long as the dyeing reproducibility of the flame retardant processing method for simultaneously dyeing polyester fiber products according to the present invention is not hindered. Examples of such disperse dyes include C.I. I. Disperse Yellow 71, 42, 51, C.I. I. Yellow disperse dyes such as Solvent Yellow 163, C.I. I. blue disperse dyes such as Disperse Blue 54, 60, 77, 165; I. Orange disperse dyes such as Disperse Orange 29 and 155 can be used, but the dyes are not limited to these.
　以下に実施例と共に比較例を挙げて、本発明を詳細に説明するが、本発明はそれら実施例によって何ら限定されるものではない。 The present invention will be described in detail below with examples and comparative examples, but the present invention is not limited by these examples.
（赤色分散染料と難燃剤の平均粒子径）
　以下において、赤色分散染料と難燃剤はいずれも、直径０．５ｍｍのガラスビーズを充填したミルを用いて、それぞれ界面活性剤の存在下に所定の平均粒子径を有するように湿式粉砕し、水分散液として用いた。 (Average particle size of red disperse dye and flame retardant)
In the following, both the red disperse dye and the flame retardant are wet-ground using a mill filled with glass beads with a diameter of 0.5 mm so as to have a predetermined average particle size in the presence of a surfactant. used as a dispersion.
　また、分散染料と難燃剤の平均粒子径はいずれも、それぞれの分散液について（株）島津製作所製レーザー回折式粒度分布測定装置ＳＡＬＤ－２０００Ｊによって粒度分布を測定して、これに基づいて求めた体積基準のメディアン径をいう。 In addition, the average particle size of both the disperse dye and the flame retardant was determined based on the particle size distribution of each dispersion measured by a laser diffraction particle size distribution analyzer SALD-2000J manufactured by Shimadzu Corporation. Refers to the volume-based median diameter.
（染色物の測色）
　以下において、得られた染色物の測色は、分光測色計ＣＭ－６００ｄ（コニカミノルタ（株）製）を用いた。 (Color measurement of dyeing)
In the following, a spectrophotometer CM-600d (manufactured by Konica Minolta, Inc.) was used to measure the color of the obtained dyed material.
　以下の実施例及び比較例においては、先ず、ポリエステルダブルピケ（目付重量２４０ｇ／ｍ２）を被処理布帛とし、これを温度１００℃において難燃剤の不存在下に分散染料で染色して得た染色物と、難燃剤の存在下に上記と同じ分散染料で染色して得た染色物のそれぞれについて測色して得たそれら染色物の間の色差△Ｅ（１００℃）と、上記被処理布帛を温度１３０℃において難燃剤の不存在下に分散染料で染色して得た染色物と、難燃剤の存在下に上記と同じ分散染料で染色して得た染色物のそれぞれについて測色して得たそれら染色物の間の色差△Ｅ（１３０℃）を求めた。 In the following examples and comparative examples, first, a polyester double picket (basis weight of 240 g/m 2 ) was used as a fabric to be treated, and this was obtained by dyeing with a disperse dye at a temperature of 100 ° C. in the absence of a flame retardant. The color difference ΔE (100° C.) between the dyed article and the dyed article obtained by dyeing with the same disperse dye as above in the presence of a flame retardant, and the above treated A dyed product obtained by dyeing a fabric with a disperse dye in the absence of a flame retardant at a temperature of 130 ° C. and a dyed product obtained by dyeing with the same disperse dye as above in the presence of a flame retardant were measured. The color difference .DELTA.E (130.degree. C.) between the dyeings obtained by
　次に、難燃剤の不存在下に温度１００℃と温度１３０℃でそれぞれ分散染料で染色して得た染色物の色差△Ｅ（染料）と、難燃剤の存在下に温度１００℃と温度１３０℃でそれぞれ分散染料で染色して得た染色物の色差△Ｅ（染料＋難燃剤）を求めた。 Next, the color difference ΔE (dye) of the dyed product obtained by dyeing with a disperse dye at a temperature of 100 ° C. and a temperature of 130 ° C. in the absence of a flame retardant, and the temperature of 100 ° C. and the temperature of 130 ° C. in the presence of a flame retardant. The color difference ΔE (dye + flame retardant) of the dyed product obtained by dyeing with each disperse dye at °C was determined.
　次いで、上記色差△Ｅ（染料）と色差△Ｅ（染料＋難燃剤）より、式（△Ｅ（染料）／△Ｅ（染料＋難燃剤））×１００の値を求め、この値を難燃剤の存在下に分散染料にて上記被処理布帛を染色したときの染色速度変化率とした。 Next, from the color difference ΔE (dye) and the color difference ΔE (dye + flame retardant), the value of the formula (ΔE (dye) / ΔE (dye + flame retardant)) × 100 is obtained, and this value is used as the flame retardant. The rate of change in dyeing speed when the treated fabric was dyed with a disperse dye in the presence of .
　本発明については、後述するように、上記△Ｅ（１００℃）、△Ｅ（１３０℃）及び（△Ｅ（染料）／△Ｅ（染料＋難燃剤））×１００の値、即ち、染色速度変化率のすべてが一定の範囲にある場合を染色再現性がすぐれるとした。 Regarding the present invention, as described later, the values of ΔE (100 ° C.), ΔE (130 ° C.) and (ΔE (dye) / ΔE (dye + flame retardant)) × 100, that is, the dyeing speed Staining reproducibility was judged to be excellent when all of the rate of change was within a certain range.
　本発明においては、上記被処理布帛を染色同時難燃加工して得られた染色物の色調を評価するに際して、国際照明委員会（ＣＩＥ）が１９７４年に策定したＬ*ａ*ｂ* 表色系による色空間によった。上記Ｌ*ａ*ｂ* 表色系において、Ｌ* 値は明度指数と呼ばれており、値が大きい程、明るいことを示し、値が小さい程、暗いことを示す。白色のＬ* 値は１００であり、黒色のＬ* 値は０である。ａ* 値とｂ* 値は色調と彩度を表し、クロマティクス指数と呼ばれている。ａ* 値が正の値方向に大きくなるほど、赤味が強くなり、負方向に大きくなるほど、緑味が強くなる。ｂ* 値が正の値方向に大きくなるほど、黄味が強くなり、負方向に大きくなるほど、青味が強くなる。 In the present invention, when evaluating the color tone of the dyed product obtained by flame retarding the treated fabric at the same time as dyeing, the L * a * b * color specification formulated by the International Commission on Illumination (CIE) in 1974 According to the color space by the system. In the L * a * b * color system, the L * value is called a brightness index, and a larger value indicates a brighter color, and a smaller value indicates a darker color. White has an L * value of 100 and black has an L * value of 0. The a * and b* values represent hue and saturation and are called chromaticity indices. As the a * value increases in the positive direction, the color becomes reddish, and as the a* value increases in the negative direction, the color becomes greenish. As the b * value increases in the positive direction, the color becomes more yellowish, and as the b* value increases in the negative direction, the color becomes more bluish.
　このようなＬ*ａ*ｂ* 表色系において、２つの色の差、即ち、色差△Ｅは、色空間における上記２つの色の座標間の距離で表される。即ち、
△Ｅ＝[(△Ｌ*)２＋(△ａ*)２＋(△ｂ*)２]１／２ In such an L * a * b * color system, the difference between two colors, ie, the color difference ΔE, is represented by the distance between the coordinates of the two colors in the color space. Namely
ΔE=[(ΔL * ) 2 +(Δa * ) 2 +(Δb * ) 2 ] 1/2
実施例１
　前記式（Ｉ）で表される平均粒子径０．８μｍの赤色分散染料０．３％ｏｗｆを含む浴比１：１０の加工浴へ被処理布帛（ポリエステルダブルピケ（目付重量２４０ｇ／ｍ２））を投入し、４０℃から毎分２℃の昇温速度で１００℃まで昇温して浴中吸尽処理し、次いで、ソーピング処理と水洗処理を行った後、脱水乾燥して、染色布帛を得た。この染色布帛を測色して、Ｌ*(100）、ａ*(100)及びｂ*(100)を求めた。 Example 1
A fabric to be treated (polyester double picket (basis weight: 240 g/m 2 ) into a processing bath with a bath ratio of 1:10 containing 0.3% owf of a red disperse dye with an average particle size of 0.8 μm represented by the formula (I) ) is added, the temperature is raised from 40 ° C. to 100 ° C. at a rate of 2 ° C. per minute, and the bath is exhausted, then soaped and washed with water, dehydrated and dried, and the dyed fabric. got This dyed fabric was colorimetrically measured to determine L * (100), a * (100) and b * (100).
　次に、上記と同じ構成にした加工浴へ上記と同じ被処理布帛を投入し、４０℃から毎分２℃の昇温速度で１３０℃まで昇温し、その温度で３０分間保持して、浴中吸尽処理し、次いで、ソーピング処理と水洗処理を行った後、脱水乾燥して、染色布帛を得た。この染色布帛を上記と同様に測色して、Ｌ*(130）、ａ*(130) 及びｂ*(130)を求めた。 Next, the same treated fabric as above is put into a processing bath having the same structure as above, and the temperature is raised from 40 ° C. to 130 ° C. at a rate of 2 ° C. per minute, and held at that temperature for 30 minutes. It was exhausted in a bath, then soaped and washed with water, and then dehydrated and dried to obtain a dyed fabric. This dyed fabric was measured in the same manner as above to determine L * (130), a * (130) and b * (130).
　別に、前記式（Ｉ）で表される平均粒子径０．８μｍの赤色分散染料０．３％ｏｗｆと共に前記式（ＶＩＩ）で表される平均粒子径０．６μｍの難燃剤リン酸エステルアミド４．０％ｏｗｆを含む浴比１：１０の加工浴に上記と同じ被処理布帛を投入し、４０℃から毎分２℃の昇温速度で１００℃まで昇温して浴中吸尽処理し、次いで、ソーピング処理と水洗処理を行った後、脱水乾燥して、染色布帛を得た。 Separately, 0.3% owf of a red disperse dye having an average particle size of 0.8 µm represented by the formula (I) and a flame retardant phosphate ester amide 4 having an average particle size of 0.6 µm represented by the formula (VII) The same treated fabric as above was put into a processing bath containing 0% owf at a bath ratio of 1:10, and the temperature was raised from 40 ° C. to 100 ° C. at a rate of 2 ° C. per minute to perform exhaust treatment in the bath. Then, after performing soaping treatment and water washing treatment, the fabric was dehydrated and dried to obtain a dyed fabric.
　上記染色布帛を前記と同様に測色して、Ｌ*(100難燃剤)、ａ*(100難燃剤)及びｂ*(100難燃剤) を求めた。 The dyed fabric was measured in the same manner as described above to determine L * (100 flame retardant), a * (100 flame retardant) and b * (100 flame retardant).
　次に、上記と同じ構成にした加工浴へ上記と同じ被処理布帛を投入し、４０℃から毎分２℃の昇温速度で１３０℃まで昇温し、その温度で３０分間保持して、浴中吸尽処理し、次いで、ソーピング処理と水洗処理を行った後、脱水乾燥して、染色布帛を得た。上記染色布帛を上記と同様に測色して、Ｌ*(130難燃剤)、ａ*(130難燃剤)及びｂ*(130難燃剤) を求めた。 Next, the same treated fabric as above is put into a processing bath having the same structure as above, and the temperature is raised from 40 ° C. to 130 ° C. at a rate of 2 ° C. per minute, and held at that temperature for 30 minutes. It was exhausted in a bath, then soaped and washed with water, and then dehydrated and dried to obtain a dyed fabric. The dyed fabric was measured in the same manner as above to determine L * (130 flame retardant), a * (130 flame retardant) and b * (130 flame retardant).
　このようにして得られた測色結果に基づいて以下の数値を求めた。 The following numerical values were obtained based on the colorimetric results obtained in this way.
（１）１００℃において、上記難燃剤の不存在下に上記分散染料にて被処理布帛を染色して得た染色布帛と、上記難燃剤の存在下に上記分散染料にて被処理布帛を染色して得た染色布帛との色差△Ｅ（１００℃）を式
△Ｅ(１００℃)＝［（Ｌ*(100)－Ｌ*(100難燃剤))２＋（ａ*(100)－ａ*(100難燃剤))２＋（ｂ*(100)－ｂ*(100難燃剤)) ２]１／２ から求めた。 (1) A dyed fabric obtained by dyeing a treated fabric with the disperse dye in the absence of the flame retardant at 100 ° C., and a treated fabric with the disperse dye in the presence of the flame retardant. The color difference ΔE (100 ° C.) from the dyed fabric obtained by the formula ΔE (100 ° C.) = [(L * (100) - L * (100 flame retardant)) 2 + (a * (100) - a * (100 flame retardant)) 2 + (b * (100) - b * (100 flame retardant)) 2 ] 1/2 .
（２）１３０℃において、上記難燃剤の不存在下に上記分散染料にて被処理布帛を染色して得た染色布帛と、上記難燃剤の存在下に上記分散染料にて被処理布帛を染色して得た染色布帛との色差△Ｅ（１３０℃）を式
△Ｅ(１３０℃)＝［（Ｌ*(130)－Ｌ*(130難燃剤)）２＋（ａ*(130)－ａ*(130難燃剤)）２＋（ｂ*(130)－ｂ*(130難燃剤)）２]１／２ から求めた。 (2) A dyed fabric obtained by dyeing a treated fabric with the disperse dye in the absence of the flame retardant at 130 ° C., and a treated fabric with the disperse dye in the presence of the flame retardant. The color difference ΔE (130 ° C.) from the dyed fabric obtained by the formula ΔE (130 ° C.) = [(L * (130) - L * (130 flame retardant)) 2 + (a * (130) - a * (130 flame retardant)) 2 + (b * (130) - b * (130 flame retardant)) 2 ] 1/2 .
（３）上記難燃剤の不存在下に上記分散染料にて、１００℃において被処理布帛を染色して得た染色布帛と、１３０℃において被処理布帛を染色して得た染色布帛との色差△Ｅ（染料）を式
△Ｅ(染料)＝［（Ｌ*(100)－Ｌ*(130)）２＋（ａ*(100)－ａ*(130)）２＋（ｂ*(100)－ｂ*(130)）２]１／２から求めた。 (3) Color difference between the dyed fabric obtained by dyeing the treated fabric at 100 ° C. with the disperse dye in the absence of the flame retardant and the dyed fabric obtained by dyeing the treated fabric at 130 ° C. ΔE (dye) is expressed by the formula ΔE (dye) = [(L * (100) - L * (130)) 2 + (a * (100) - a * (130)) 2 + (b * (100) −b * (130)) 2 ] 1/2 .
（４）上記難燃剤の存在下に上記分散染料にて、１００℃において被処理布帛を染色して得た染色布帛と、１３０℃において被処理布帛を染色して得た染色布帛との色差△Ｅ（染料＋難燃剤）を式
△Ｅ(染料＋難燃剤)＝［（Ｌ*(100難燃剤)－Ｌ*(130難燃剤))２＋（ａ*(100難燃剤)－ａ*(130難燃剤))２＋（ｂ*(100難燃剤)－ｂ*(130難燃剤)) ２]１／２から求めた。 (4) Color difference Δ between the dyed fabric obtained by dyeing the treated fabric at 100 ° C. with the disperse dye in the presence of the flame retardant and the dyed fabric obtained by dyeing the treated fabric at 130 ° C. E (dye + flame retardant) is expressed by the formula △ E (dye + flame retardant) = [(L * (100 flame retardant) - L * (130 flame retardant)) 2 + (a * (100 flame retardant) - a * ( 130 flame retardant)) 2 + (b * (100 flame retardant) - b * (130 flame retardant)) 2 ] 1/2 .
　次に、前述したように、下記式
（△Ｅ（染料）／△Ｅ（染料＋難燃剤））×１００
によって得られる値を上記分散染料を含む加工浴に上記難燃剤を加えた場合の上記分散染料の染色速度変化率とした。 Next, as described above, the following formula (ΔE (dye) / ΔE (dye + flame retardant)) × 100
The value obtained by the disperse dye dyeing speed change rate when the flame retardant was added to the processing bath containing the disperse dye.
（評価）
　△Ｅ（１００℃）、△Ｅ（１３０℃）及び染色速度変化率の評価基準は下記のとおりである。 (evaluation)
Evaluation criteria for ΔE (100° C.), ΔE (130° C.) and dyeing speed change rate are as follows.
　△Ｅ（１００℃）は５．００未満を〇（適正）、５．００以上を×（不適）とした。
△Ｅ（１３０℃）は５．００未満を〇（適正）、５．００以上を×（不適）とした。 ΔE (100° C.) was evaluated as ◯ (appropriate) when less than 5.00 and x (unsuitable) when 5.00 or more.
ΔE (130° C.) was evaluated as ◯ (appropriate) when less than 5.00 and x (unsuitable) when 5.00 or more.
　染色速度変化率の値は、△Ｅ（染料）が△Ｅ（染料＋難燃剤）よりも大きいとき、１００を超える。即ち、分散染料と共に難燃剤を併用することによって、染色速度が速くなったということができる。△Ｅ（染料）が△Ｅ（染料＋難燃剤）よりも小さいときは、値は１００以下である。即ち、分散染料と共に難燃剤を併用することによって、染色速度が遅くなったということができるから、難燃剤が染料の染着を阻害したということができる。 The dyeing speed change rate value exceeds 100 when ΔE (dye) is greater than ΔE (dye + flame retardant). That is, it can be said that the dyeing speed was increased by using the flame retardant together with the disperse dye. When ΔE(dye) is less than ΔE(dye+flame retardant), the value is 100 or less. That is, it can be said that the dyeing speed is slowed down by using the flame retardant together with the disperse dye, so it can be said that the flame retardant inhibits the dyeing.
　染色速度が速すぎるときは染色むらを生じ、遅くなるときは発色不良となることから、本発明においては、上記染色速度変化率が１２０～１００の範囲にあるときを〇（適正）とし、１００未満であるとき及び１２１以上であるときを×（不適）とした。 When the dyeing speed is too fast, uneven dyeing occurs, and when it is too slow, the color development is poor. When it was less than or 121 or more, it was marked as x (unsuitable).
実施例２～５
　実施例１において、前記式（Ｉ）で表される平均粒子径０．８μｍの赤色分散染料に代えて、それぞれ前記式（ＩＩ）～（Ｖ）で表される、いずれも平均粒子径０．８μｍの赤色分散染料を用いた以外は同様にして、染色布帛を得た。 Examples 2-5
In Example 1, instead of the red disperse dye represented by formula (I) having an average particle size of 0.8 μm, each of the formulas (II) to (V) represented by each of the above formulas (II) to (V) having an average particle size of 0.8 μm was used. A dyed fabric was obtained in the same manner except that an 8 μm red disperse dye was used.
　上記染色布帛について、実施例１と同様に測色して、△Ｅ（１００℃）、△Ｅ（１３０℃）及び染色速度変化率を求めた。実施例１から５による評価結果を表１に示す。 For the above dyed fabric, colorimetry was performed in the same manner as in Example 1 to obtain ΔE (100°C), ΔE (130°C), and the rate of change in dyeing speed. Table 1 shows the evaluation results of Examples 1 to 5.
実施例６～１０
　実施例１～５において、前記式（Ｉ）で表される平均粒子径０．８μｍの赤色分散染料０．３％ｏｗｆに代えて、それぞれ前記式（Ｉ）～（Ｖ）で表されるいずれも平均粒子径０．８μｍの赤色分散染料３．０％ｏｗｆを用いた以外は、同様にして、染色布帛を得た。 Examples 6-10
In Examples 1 to 5, instead of the red disperse dye 0.3% owf having an average particle size of 0.8 μm represented by the formula (I), any of the formulas (I) to (V) respectively A dyed fabric was obtained in the same manner, except that 3.0% owf of a red disperse dye having an average particle size of 0.8 μm was used.
　上記染色布帛について、実施例１と同様に測色して、△Ｅ（１００℃）、△Ｅ（１３０℃）及び染色速度変化率を求めた。実施例６から１０による評価結果を表２に示す。 For the above dyed fabric, colorimetry was performed in the same manner as in Example 1 to obtain ΔE (100°C), ΔE (130°C), and the rate of change in dyeing speed. Table 2 shows the evaluation results of Examples 6 to 10.
実施例１１～１５
　実施例１～５において、前記式（ＶＩＩ）で表される平均粒子径０．６μｍの難燃剤リン酸エステルアミド４．０％ｏｗｆに代えて、それぞれ前記式（ＶＩＩ）で表される平均粒子径０．６μｍの難燃剤リン酸エステルアミド８．０％ｏｗｆを用いた以外は、実施例１～５におけると同様に、前記式（Ｉ）～（Ｖ）で表されるいずれも平均粒子径０．８μｍの赤色分散染料０．３％ｏｗｆを用いて、同様にして染色布帛を得た。 Examples 11-15
In Examples 1 to 5, instead of the flame retardant phosphoric acid ester amide 4.0% owf having an average particle size of 0.6 μm represented by the formula (VII), the average particles represented by the formula (VII) In the same manner as in Examples 1 to 5, except that 8.0% owf of a flame retardant phosphoric acid ester amide having a diameter of 0.6 μm was used, all of the average particle sizes represented by the formulas (I) to (V) A dyed fabric was similarly obtained using 0.8 μm red disperse dye 0.3% owf.
　上記染色布帛について、実施例１と同様に測色して、△Ｅ（１００℃）、△Ｅ（１３０℃）及び染色速度変化率を求めた。実施例１１から１５による評価結果を表３に示す。 For the above dyed fabric, colorimetry was performed in the same manner as in Example 1 to obtain ΔE (100°C), ΔE (130°C), and the rate of change in dyeing speed. Table 3 shows the evaluation results of Examples 11 to 15.
実施例１６～２０
　実施例１～５において、前記式（ＶＩＩ）で表される平均粒子径０．６μｍの難燃剤リン酸エステルアミド４．０％ｏｗｆに代えて、それぞれ前記式（ＶＩＩ）で表される平均粒子径０．６μｍの難燃剤リン酸エステルアミド１．０％ｏｗｆを用いた以外は、実施例１～５におけると同様に、前記式（Ｉ）～（Ｖ）で表されるいずれも平均粒子径０．８μｍの赤色分散染料０．３％ｏｗｆを用いて、同様にして染色布帛を得た。 Examples 16-20
In Examples 1 to 5, instead of the flame retardant phosphoric acid ester amide 4.0% owf having an average particle size of 0.6 μm represented by the formula (VII), the average particles represented by the formula (VII) In the same manner as in Examples 1 to 5, except that 1.0% owf of a flame retardant phosphoric acid ester amide having a diameter of 0.6 μm was used, all of the average particle sizes represented by the formulas (I) to (V) A dyed fabric was similarly obtained using 0.8 μm red disperse dye 0.3% owf.
　上記染色布帛について、実施例１と同様に、測色して、△Ｅ（１００℃）、△Ｅ（１３０℃）及び染色速度変化率を求めた。実施例１６から２０による評価結果を表４に示す。 For the above dyed fabric, colorimetry was performed in the same manner as in Example 1 to obtain ΔE (100°C), ΔE (130°C) and the rate of change in dyeing speed. Table 4 shows the evaluation results of Examples 16 to 20.
実施例２１～２５
　実施例１～５において、赤色分散染料として、前記式（Ｉ）～（Ｖ）で表される平均粒子径０．８μｍのキノン系赤色分散染料のいずれかと前記式（ＶＩ）で表される平均粒子径０．８μｍのアゾ系赤色分散染料を用いた以外は、同様にして染色布帛を得た。 Examples 21-25
In Examples 1 to 5, as the red disperse dye, any of the quinone red disperse dyes having an average particle size of 0.8 μm represented by the formulas (I) to (V) and the average represented by the formula (VI) A dyed fabric was obtained in the same manner except that an azo red disperse dye having a particle size of 0.8 μm was used.
　上記染色布帛について、実施例１と同様に測色して、△Ｅ（１００℃）、△Ｅ（１３０℃）及び染色速度変化率を求めた。実施例２１から２５による評価結果を表５に示す。 For the above dyed fabric, colorimetry was performed in the same manner as in Example 1 to obtain ΔE (100°C), ΔE (130°C), and the rate of change in dyeing speed. Table 5 shows the evaluation results of Examples 21 to 25.
比較例１
　実施例１において、前記式（ＶＩＩ）で表される難燃剤リン酸エステルアミドに代えて、難燃剤として平均粒子径０．６μｍの下記式（ＶＩＩＩ） Comparative example 1
In Example 1, instead of the flame retardant phosphate amide represented by the formula (VII), the following formula (VIII) having an average particle size of 0.6 μm was used as a flame retardant.
Figure JPOXMLDOC01-appb-C000027
  
Figure JPOXMLDOC01-appb-C000027
  
で表されるレゾルシノールビス（２，６－ジキシレニルホスフェート）を用いた以外は、同様にして、染色布帛を得た。 A dyed fabric was obtained in the same manner except that resorcinol bis (2,6-dixylenyl phosphate) represented by was used.
比較例２
　実施例１において、前記式（ＶＩＩ）で表される難燃剤リン酸エステルアミドに代えて、難燃剤として平均粒子径０．６μｍの下記式（ＩＸ） Comparative example 2
In Example 1, instead of the flame retardant phosphate amide represented by the formula (VII), the following formula (IX) having an average particle size of 0.6 μm was used as a flame retardant.
Figure JPOXMLDOC01-appb-C000028
  
Figure JPOXMLDOC01-appb-C000028
  
で表される１０－ベンジル－９，１０－ジヒドロ－９－オキサ―１０－ホスファフェナンスレン―１０－オキシドを用いた以外は、同様にして、染色布帛を得た。 A dyed fabric was obtained in the same manner except that 10-benzyl-9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide represented by was used.
比較例３
　実施例１において、前記式（ＶＩＩ）で表される難燃剤リン酸エステルアミドに代えて、難燃剤として平均粒子径０．６μｍの下記式（Ｘ） Comparative example 3
In Example 1, instead of the flame retardant phosphate amide represented by the formula (VII), the following formula (X) having an average particle size of 0.6 μm was used as a flame retardant.
Figure JPOXMLDOC01-appb-C000029
  
Figure JPOXMLDOC01-appb-C000029
  
で表される２－フェノキシエチルジフェニルホスフェートを用いた以外は、同様にして、染色布帛を得た。 A dyed fabric was obtained in the same manner except that 2-phenoxyethyl diphenyl phosphate represented by was used.
比較例４
　実施例１において、前記式（ＶＩＩ）で表される難燃剤リン酸エステルアミドに代えて、難燃剤として平均粒子径０．６μｍの下記式（ＸＩ） Comparative example 4
In Example 1, instead of the flame retardant phosphate amide represented by the formula (VII), the following formula (XI) having an average particle size of 0.6 μm was used as the flame retardant.
Figure JPOXMLDOC01-appb-C000030
  
Figure JPOXMLDOC01-appb-C000030
  
で表される５，５－ジメチル－２－（２’－フェニルフェノキシ）－１，３，２－ジオキサホスホリナン－２－オキシドを用いた以外は、同様にして、染色布帛を得た。 A dyed fabric was obtained in the same manner except that 5,5-dimethyl-2-(2'-phenylphenoxy)-1,3,2-dioxaphosphorinane-2-oxide represented by was used.
比較例５
　実施例１において、前記式（ＶＩＩ）で表される難燃剤リン酸エステルアミドに代えて、難燃剤として平均粒子径０．６μｍの下記式（ＸＩＩ） Comparative example 5
In Example 1, instead of the flame retardant phosphate amide represented by the formula (VII), the following formula (XII) having an average particle size of 0.6 μm was used as the flame retardant.
Figure JPOXMLDOC01-appb-C000031
  
Figure JPOXMLDOC01-appb-C000031
  
で表されるｐ－クレジルホスフェートを用いた以外は、同様にして染色布帛を得た。 A dyed fabric was obtained in the same manner except that p-cresyl phosphate represented by was used.
比較例６
　実施例１において、前記式（ＶＩＩ）で表される難燃剤リン酸エステルアミドに代えて、難燃剤として平均粒子径０．６μｍの下記式（ＸＩＩＩ） Comparative example 6
In Example 1, instead of the flame retardant phosphate amide represented by the formula (VII), the following formula (XIII) having an average particle size of 0.6 μm was used as a flame retardant.
Figure JPOXMLDOC01-appb-C000032
  
Figure JPOXMLDOC01-appb-C000032
  
で表されるトリス（２，３－ジブロモプロピル）イソシアヌレートを用いた以外は、同様にして染色布帛を得た。 A dyed fabric was obtained in the same manner except that tris (2,3-dibromopropyl) isocyanurate represented by was used.
　上記比較例１～６において得た染色布帛について、実施例１と同様に測色して、△Ｅ（１００℃）、△Ｅ（１３０℃）及び染色速度変化率を求めた。比較例１から６による評価結果を表６に示す。 For the dyed fabrics obtained in Comparative Examples 1 to 6 above, the colors were measured in the same manner as in Example 1 to determine ΔE (100°C), ΔE (130°C) and the rate of change in dyeing speed. Table 6 shows the evaluation results of Comparative Examples 1 to 6.
比較例７～１２
　比較例１～６において、式（Ｉ）で表される赤色分散染料に代えて、それぞれ式（ＩＩ）で表される赤色分散染料を用いた以外は同様にして、染色布帛を得た。 Comparative Examples 7-12
Dyed fabrics were obtained in the same manner as in Comparative Examples 1 to 6, except that the red disperse dye represented by formula (II) was used instead of the red disperse dye represented by formula (I).
　上記染色布帛について、実施例１と同様に測色して、△Ｅ（１００℃）、△Ｅ（１３０℃）及び染色速度変化率を求めた。比較例７から１２による評価結果を表７に示す。 For the above dyed fabric, colorimetry was performed in the same manner as in Example 1 to obtain ΔE (100°C), ΔE (130°C), and the rate of change in dyeing speed. Table 7 shows the evaluation results of Comparative Examples 7 to 12.
比較例１３～１８
　比較例１～６において、式（Ｉ）で表される赤色分散染料に代えて、それぞれ式（ＩＩＩ）で表される赤色分散染料を用いた以外は同様にして、染色布帛を得た。 Comparative Examples 13-18
Dyed fabrics were obtained in the same manner as in Comparative Examples 1 to 6, except that the red disperse dye represented by formula (III) was used in place of the red disperse dye represented by formula (I).
　上記染色布帛について、実施例１と同様に測色して、△Ｅ（１００℃）、△Ｅ（１３０℃）及び染色速度変化率を求めた。比較例１３から１８による評価結果を表８に示す。 For the above dyed fabric, colorimetry was performed in the same manner as in Example 1 to obtain ΔE (100°C), ΔE (130°C), and the rate of change in dyeing speed. Table 8 shows the evaluation results of Comparative Examples 13 to 18.
比較例１９～２４
　比較例１～６において、式（Ｉ）で表される赤色分散染料に代えて、それぞれ式（ＩＶ）で表される赤色分散染料を用いた以外は同様にして、染色布帛を得た。 Comparative Examples 19-24
Dyed fabrics were obtained in the same manner as in Comparative Examples 1 to 6, except that the red disperse dye represented by formula (IV) was used in place of the red disperse dye represented by formula (I).
　上記染色布帛について、実施例１と同様に測色して、△Ｅ（１００℃）、△Ｅ（１３０℃）及び染色速度変化率を求めた。比較例１９から２４による評価結果を表９に示す。 For the above dyed fabric, colorimetry was performed in the same manner as in Example 1 to obtain ΔE (100°C), ΔE (130°C), and the rate of change in dyeing speed. Table 9 shows the evaluation results of Comparative Examples 19 to 24.
比較例２５～３０
　比較例１～６において、式（Ｉ）で表される赤色分散染料に代えて、それぞれ式（Ｖ）で表される赤色分散染料を用いた以外は同様にして、染色布帛を得た。 Comparative Examples 25-30
Dyed fabrics were obtained in the same manner as in Comparative Examples 1 to 6, except that the red disperse dye represented by formula (I) was replaced with the red disperse dye represented by formula (V).
　上記染色布帛について、実施例１と同様に測色して、△Ｅ（１００℃）、△Ｅ（１３０℃）及び染色速度変化率を求めた。比較例２５から３０による評価結果を表１０に示す。 For the above dyed fabric, colorimetry was performed in the same manner as in Example 1 to obtain ΔE (100°C), ΔE (130°C), and the rate of change in dyeing speed. Table 10 shows the evaluation results of Comparative Examples 25 to 30.
比較例３１
　実施例１において、式（Ｉ）で表される赤色分散染料３．０％ｏｗｆを用いると共に、前記式（ＶＩＩ）で表される難燃剤に代えて、前記式（ＸＩＩＩ）で表される平均粒子径０．６μｍのトリス（２，３－ジブロモプロピル）イソシアヌレートを用いた以外は同様にして、染色布帛を得た。 Comparative example 31
In Example 1, 3.0% owf of the red disperse dye represented by the formula (I) was used, and instead of the flame retardant represented by the formula (VII), the average represented by the formula (XIII) A dyed fabric was obtained in the same manner except that tris(2,3-dibromopropyl)isocyanurate with a particle size of 0.6 μm was used.
比較例３２
　実施例１において、式（Ｉ）で表される赤色分散染料に代えて、前記式（ＩＩ）で表される平均粒子径０．８μｍの赤色分散染料３．０％ｏｗｆを用いると共に、前記式（ＶＩＩ）で表される難燃剤に代えて、前記式（ＶＩＩＩ）で表される平均粒子径０．６μｍのレゾルシノールビス（２，６－ジキシレニルホスフェート）を用いた以外は同様にして、染色布帛を得た。 Comparative example 32
In Example 1, instead of the red disperse dye represented by formula (I), a red disperse dye 3.0% owf having an average particle size of 0.8 μm represented by formula (II) was used, and the formula In the same manner, except that resorcinol bis(2,6-dixylenyl phosphate) having an average particle size of 0.6 μm represented by the formula (VIII) was used instead of the flame retardant represented by (VII). A dyed fabric was obtained.
比較例３３
　実施例１において、式（Ｉ）で表される赤色分散染料に代えて、前記式（ＩＩＩ）で表される平均粒子径０．８μｍの赤色分散染料３．０％ｏｗｆを用いると共に、前記式（ＶＩＩ）で表される難燃剤に代えて、前記式（Ｘ）で表される平均粒子径０．６μｍの２－フェノキシエチルジフェニルホスフェートを用いた以外は同様にして、染色布帛を得た。 Comparative example 33
In Example 1, instead of the red disperse dye represented by formula (I), a red disperse dye 3.0% owf having an average particle size of 0.8 μm represented by formula (III) was used, and the formula A dyed fabric was obtained in the same manner except that the flame retardant represented by (VII) was replaced with 2-phenoxyethyldiphenyl phosphate represented by the formula (X) having an average particle size of 0.6 μm.
比較例３４
　実施例１において、式（Ｉ）で表される赤色分散染料に代えて、前記式（ＩＩＩ）で表される平均粒子径０．８μｍの赤色分散染料３．０％ｏｗｆを用いると共に、前記式（ＶＩＩ）で表される難燃剤に代えて、前記式（ＸＩ）で表される平均粒子径０．６μｍの５，５－ジメチル－２－（２’－フェニルフェノキシ）－１，３，２－ジオキサホスホリナン－２－オキシドを用いた以外は同様にして、染色布帛を得た。 Comparative example 34
In Example 1, instead of the red disperse dye represented by formula (I), a red disperse dye 3.0% owf having an average particle size of 0.8 μm represented by formula (III) was used, and the formula 5,5-dimethyl-2-(2′-phenylphenoxy)-1,3,2 with an average particle size of 0.6 μm represented by the formula (XI) instead of the flame retardant represented by (VII) - A dyed fabric was obtained in the same manner, except that dioxaphosphorinane-2-oxide was used.
比較例３５
　実施例１において、式（Ｉ）で表される赤色分散染料に代えて、前記式（ＩＶ）で表される平均粒子径０．８μｍの赤色分散染料３．０％ｏｗｆを用いると共に、前記式（ＶＩＩ）で表される難燃剤に代えて、前記式（ＩＸ）で表される平均粒子径０．６μｍの１０－ベンジル－９，１０－ジヒドロ－９－オキサ―１０－ホスファフェナンスレン―１０－オキシドを用いた以外は同様にして、染色布帛を得た。 Comparative example 35
In Example 1, instead of the red disperse dye represented by formula (I), 3.0% owf of red disperse dye having an average particle size of 0.8 μm represented by formula (IV) was used, and the formula 10-benzyl-9,10-dihydro-9-oxa-10-phosphaphenanthrene having an average particle size of 0.6 μm represented by the formula (IX) instead of the flame retardant represented by (VII) A dyed fabric was obtained in the same manner except that -10-oxide was used.
比較例３６
　実施例１において、式（Ｉ）で表される赤色分散染料に代えて、前記式（ＩＶ）で表される平均粒子径０．８μｍの赤色分散染料３．０％ｏｗｆを用いると共に、前記式（ＶＩＩ）で表される難燃剤に代えて、前記式（ＸＩ）で表される平均粒子径０．６μｍの５，５－ジメチル－２－（２’－フェニルフェノキシ）－１，３，２－ジオキサホスホリナン－２－オキシドを用いた以外は同様にして、染色布帛を得た。 Comparative example 36
In Example 1, instead of the red disperse dye represented by formula (I), 3.0% owf of red disperse dye having an average particle size of 0.8 μm represented by formula (IV) was used, and the formula 5,5-dimethyl-2-(2′-phenylphenoxy)-1,3,2 with an average particle size of 0.6 μm represented by the formula (XI) instead of the flame retardant represented by (VII) - A dyed fabric was obtained in the same manner, except that dioxaphosphorinane-2-oxide was used.
　上記比較例３１～３６において得た染色布帛について、実施例１と同様に測色して、△Ｅ（１００℃）、△Ｅ（１３０℃）及び染色速度変化率を求めた。比較例３１から３６による評価結果を表１１に示す。 The dyed fabrics obtained in Comparative Examples 31 to 36 were colorimetrically measured in the same manner as in Example 1 to determine ΔE (100°C), ΔE (130°C), and dyeing speed change rate. Table 11 shows the evaluation results of Comparative Examples 31 to 36.
Figure JPOXMLDOC01-appb-T000033
  
Figure JPOXMLDOC01-appb-T000033
  
Figure JPOXMLDOC01-appb-T000034
  
Figure JPOXMLDOC01-appb-T000034
  
Figure JPOXMLDOC01-appb-T000035
  
Figure JPOXMLDOC01-appb-T000035
  
Figure JPOXMLDOC01-appb-T000036
  
Figure JPOXMLDOC01-appb-T000036
  
Figure JPOXMLDOC01-appb-T000037
  
Figure JPOXMLDOC01-appb-T000037
  
Figure JPOXMLDOC01-appb-T000038
  
Figure JPOXMLDOC01-appb-T000038
  
Figure JPOXMLDOC01-appb-T000039
  
Figure JPOXMLDOC01-appb-T000039
  
Figure JPOXMLDOC01-appb-T000040
  
Figure JPOXMLDOC01-appb-T000040
  
Figure JPOXMLDOC01-appb-T000041
  
Figure JPOXMLDOC01-appb-T000041
  
Figure JPOXMLDOC01-appb-T000042
  
Figure JPOXMLDOC01-appb-T000042
  
Figure JPOXMLDOC01-appb-T000043
  
Figure JPOXMLDOC01-appb-T000043
  
　表１は、前記式（ＶＩＩ）で表される難燃剤４．０％оｗｆ量の存在下に前記式（Ｉ）～（Ｖ）で表されるキノン系赤色分散染料のいずれを０．３％оｗｆ量で用いても、ポリエステル系繊維からなる被処理布帛を染色したとき、色差△Ｅ（１００℃）と△Ｅ（１３０℃）が共に小さく、適正であり、染色速度変化率もまた、適正であることを示す。 Table 1 shows 0.3% of any of the quinone red disperse dyes represented by the formulas (I) to (V) in the presence of 4.0% of the flame retardant represented by the formula (VII). Even when used in the amount of wf, when the treated fabric made of polyester fiber is dyed, both the color difference ΔE (100 ° C.) and ΔE (130 ° C.) are small and appropriate, and the dyeing speed change rate is also appropriate. indicates that
　即ち、１００℃と１３０℃において、前記式（ＶＩＩ）で表される難燃剤の不存在下に、それぞれ前記式（Ｉ）～（Ｖ）で表されるキノン系赤色分散染料にて被処理布帛を染色して得られた染色布帛と、上記難燃剤の存在下に上記キノン系赤色分散染料にて被処理布帛を染色して得られた染色布帛との色差が小さく、更に、前述した染色速度変化率が適正であることから、上記キノン系赤色分散染料に上記難燃剤を併用しても、上記難燃剤の不存在下に上記キノン系赤色分散染料を用いて染色する場合に比べて、染色速度変化率が小さいということができる。 That is, at 100 ° C. and 130 ° C., in the absence of the flame retardant represented by the formula (VII), the fabric to be treated with the quinone red disperse dye represented by the formulas (I) to (V), respectively. and the dyed fabric obtained by dyeing the treated fabric with the quinone red disperse dye in the presence of the flame retardant is small, and the dyeing speed described above is small. Since the rate of change is appropriate, even if the flame retardant is used in combination with the quinone red disperse dye, compared to the case of dyeing using the quinone red disperse dye in the absence of the flame retardant, dyeing It can be said that the speed change rate is small.
　表２は、１００℃と１３０℃において、前記式（ＶＩＩ）で表される難燃剤４．０％оｗｆ量の存在下に前記式（Ｉ）～（Ｖ）で表されるキノン系赤色分散染料のいずれを３．０％оｗｆ量で用いても、得られる染色物は、色差△Ｅ（１００℃）と△Ｅ（１３０℃）が共に小さく、適正であり、染色速度変化率もまた、適正であることを示す。 Table 2 shows the quinone red disperse dyes represented by the formulas (I) to (V) in the presence of 4.0% of the flame retardant represented by the formula (VII) at 100 ° C. and 130 ° C. 3.0% wf amount, the obtained dyed product has both small color difference ΔE (100°C) and ΔE (130°C) and is appropriate, and the rate of change in dyeing speed is also appropriate. indicates that
　表３は、１００℃と１３０℃において、前記式（ＶＩＩ）で表される難燃剤８．０％оｗｆ量の存在下に前記式（Ｉ）～（Ｖ）で表されるキノン系赤色分散染料のいずれを０．３％оｗｆ量で用いても、得られる染色物は、色差△Ｅ（１００℃）と△Ｅ（１３０℃）が共に小さく、適正であり、染色速度変化率もまた、適正であることを示す。 Table 3 shows the quinone red disperse dyes represented by the formulas (I) to (V) in the presence of 8.0% of the flame retardant represented by the formula (VII) at 100 ° C. and 130 ° C. 0.3% wf amount, the resulting dyed product has both small color difference ΔE (100° C.) and ΔE (130° C.) and is appropriate, and the rate of change in dyeing speed is also appropriate. indicates that
　表４は、１００℃と１３０℃において、前記式（ＶＩＩ）で表される難燃剤１．０％оｗｆ量の存在下に前記式（Ｉ）～（Ｖ）で表されるキノン系赤色分散染料のいずれを０．３％оｗｆ量で用いても、得られる染色物は、色差△Ｅ（１００℃）と△Ｅ（１３０℃）が共に小さく、適正であり、染色速度変化率もまた、適正であることを示す。 Table 4 shows the quinone red disperse dyes represented by the formulas (I) to (V) in the presence of 1.0% of the flame retardant represented by the formula (VII) at 100 ° C. and 130 ° C. 0.3% wf amount, the resulting dyed product has both small color difference ΔE (100° C.) and ΔE (130° C.) and is appropriate, and the rate of change in dyeing speed is also appropriate. indicates that
　表５は、１００℃と１３０℃において、前記式（ＶＩＩ）で表される難燃剤４．０％оｗｆ量の存在下に前記式（Ｉ）～（Ｖ）で表されるキノン系赤色分散染料のいずれかの０．３％оｗｆ量と前記式（ＶＩ）で表されるアゾ系赤色分散染料０．３％оｗｆ量を用いても、得られる染色物はいずれも、色差△Ｅ（１００℃）と△Ｅ（１３０℃）が共に小さく、適正であり、染色速度変化率もまた、適正であることを示す。 Table 5 shows the quinone red disperse dyes represented by the formulas (I) to (V) in the presence of 4.0% of the flame retardant represented by the formula (VII) at 100 ° C. and 130 ° C. and 0.3% of the azo red disperse dye represented by the above formula (VI), the resulting dyed product has a color difference ΔE (100°C ) and ΔE (130° C.) are both small and appropriate, and the dyeing speed change rate is also appropriate.
　以上のように、本発明に従って、前記式（Ｉ）から（Ｖ）で表されるキノン系赤色分散染料から選ばれる少なくとも１種か、又は前記式（Ｉ）から（Ｖ）で表されるキノン系赤色分散染料から選ばれる少なくとも１種と前記式（ＶＩ）で表されるアゾ系赤色分散染料と、前記式（ＶＩＩ）で表される難燃剤リン酸エステルアミドを含む加工浴にポリエステル系繊維品を浸漬し、加熱する染色同時難燃加工方法によれば、難燃剤の不存在下に赤色分散染料にてポリエステル系繊維品を染色した場合に比べて、温度１００℃と１３０℃において、上記赤色分散染料と上記難燃剤の使用量を種々に変化させて、被処理布帛を染色同時難燃加工しても、上記色差△Ｅ（１００℃）と△Ｅ（１３０℃）が共に小さく、適正であると共に、染色速度変化率もまた、適正である。かくして、本発明によれば、染色再現性よく、ポリエステル系繊維品を染色同時難燃加工することができる。 As described above, according to the present invention, at least one selected from the quinone red disperse dyes represented by the formulas (I) to (V), or the quinones represented by the formulas (I) to (V) Polyester fiber in a processing bath containing at least one selected from red disperse dyes, the azo red disperse dye represented by the formula (VI), and the flame retardant phosphate ester amide represented by the formula (VII) According to the dyeing simultaneous flame retardant treatment method in which the product is immersed and heated, at temperatures of 100 ° C. and 130 ° C., the above Even if the amount of the red disperse dye and the flame retardant used is varied and the treated fabric is subjected to flame retardant treatment at the same time as dyeing, both the color differences ΔE (100 ° C.) and ΔE (130 ° C.) are small and appropriate. and the dyeing speed change rate is also appropriate. Thus, according to the present invention, it is possible to simultaneously dye and flame retard polyester textiles with good dyeing reproducibility.
　これに対して、表６は、前記式（ＶＩＩ）で表される難燃剤に代えて、前記式（ＶＩＩＩ）～（ＸＩＩＩ）で表される従来から知られている代表的な難燃剤の存在下に、前記式（Ｉ）で表されるキノン系赤色分散染料を用いて、ポリエステル系繊維品を染色したときの結果を示し、比較例１～５においては、色差△Ｅ（１００℃）及び染色速度変化率の少なくとも１つが不適であったが、比較例６においては、色差△Ｅ（１００℃）、△Ｅ（１３０℃）及び染色速度変化率のすべてが適正であった。比較例６については後に別の結果を示す。 On the other hand, Table 6 shows the existence of conventionally known representative flame retardants represented by the formulas (VIII) to (XIII) instead of the flame retardant represented by the formula (VII). Below, using the quinone-based red disperse dye represented by the formula (I), the results of dyeing polyester-based textiles are shown. At least one of the dyeing speed change rate was unsuitable, but in Comparative Example 6, all of the color difference ΔE (100° C.), ΔE (130° C.) and the dyeing speed change rate were proper. Another result of Comparative Example 6 will be shown later.
　同様に表７は、比較例７～１２において、前記式（ＶＩＩ）で表される難燃剤に代えて、前記式（ＶＩＩＩ）～（ＸＩＩＩ）で表される従来から知られている代表的な難燃剤の存在下に、前記式（ＩＩ）で表されるキノン系赤色分散染料をそれぞれ用いて、ポリエステル系繊維品を染色したときの結果を示す。 Similarly, Table 7 shows, in Comparative Examples 7 to 12, instead of the flame retardant represented by the formula (VII), typical conventionally known representatives represented by the formulas (VIII) to (XIII) The results of dyeing polyester textiles with each of the quinone red disperse dyes represented by the formula (II) in the presence of a flame retardant are shown.
　比較例８～１２においては、色差△Ｅ（１００℃）及び染色速度変化率の少なくとも１つが不適であったが、比較例７においては、色差△Ｅ（１００℃）、△Ｅ（１３０℃）及び染色速度変化率のすべてが適正であった。比較例７については後に別の結果を示す。 In Comparative Examples 8 to 12, at least one of color difference ΔE (100°C) and dyeing speed change rate was unsuitable, but in Comparative Example 7, color difference ΔE (100°C) and ΔE (130°C) were unsuitable. and dyeing rate change rate were all appropriate. Another result of Comparative Example 7 will be shown later.
　表８は、比較例１３～１８において、前記式（ＶＩＩ）で表される難燃剤に代えて、前記式（ＶＩＩＩ）～（ＸＩＩＩ）で表される従来から知られている代表的な難燃剤の存在下に、前記式（ＩＩＩ）で表されるキノン系赤色分散染料をそれぞれ用いて、ポリエステル系繊維品を染色したときの結果を示す。 Table 8 shows, in Comparative Examples 13 to 18, instead of the flame retardant represented by the formula (VII), conventionally known typical flame retardants represented by the formulas (VIII) to (XIII) In the presence of, each of the quinone red disperse dyes represented by the formula (III) is used to show the results when polyester textiles are dyed.
　比較例１３、１４、１７及び１８においては、色差△Ｅ（１００℃）及び染色速度変化率の少なくとも１つが不適であったが、比較例１５及び１６においては、色差△Ｅ（１００℃）、△Ｅ（１３０℃）及び染色速度変化率のすべてが適正であった。比較例１５及び１６については後に別の結果を示す。 In Comparative Examples 13, 14, 17 and 18, at least one of the color difference ΔE (100°C) and the dyeing speed change rate was unsuitable, but in Comparative Examples 15 and 16, the color difference ΔE (100°C) ΔE (130° C.) and dyeing rate change were all correct. Other results for Comparative Examples 15 and 16 will be shown later.
　表９は、比較例１９～２４において、前記式（ＶＩＩ）で表される難燃剤に代えて、前記式（ＶＩＩＩ）～（ＸＩＩＩ）で表される従来から知られている代表的な難燃剤の存在下に、前記式（ＩＶ）で表されるキノン系赤色分散染料をそれぞれ用いて、ポリエステル系繊維品を染色したときの結果を示す。 Table 9 shows typical conventionally known flame retardants represented by the formulas (VIII) to (XIII) instead of the flame retardant represented by the formula (VII) in Comparative Examples 19 to 24. In the presence of, each of the quinone-based red disperse dyes represented by the formula (IV) is used to dye a polyester-based textile product.
　比較例１９、２１、２３及び２４においては、色差△Ｅ（１００℃）及び染色速度変化率の少なくとも１つが不適であったが、比較例２０及び２２においては、色差△Ｅ（１００℃）、△Ｅ（１３０℃）及び染色速度変化率のすべてが適正であった。比較例２０及び２２については後に別の結果を示す。 In Comparative Examples 19, 21, 23 and 24, at least one of the color difference ΔE (100°C) and the dyeing speed change rate was unsuitable, but in Comparative Examples 20 and 22 the color difference ΔE (100°C) ΔE (130° C.) and dyeing rate change were all correct. Other results for Comparative Examples 20 and 22 are shown later.
　表１０は、比較例２５～３０において、前記式（ＶＩＩ）で表される難燃剤に代えて、前記式（ＶＩＩＩ）～（ＸＩＩＩ）で表される従来から知られている代表的な難燃剤の存在下に、前記式（Ｖ）で表されるキノン系赤色分散染料をそれぞれ用いて、ポリエステル系繊維品を染色したときの結果を示す。 Table 10 shows typical conventionally known flame retardants represented by the formulas (VIII) to (XIII) in place of the flame retardant represented by the formula (VII) in Comparative Examples 25 to 30. In the presence of, each of the quinone-based red disperse dyes represented by the formula (V) is used to show the results of dyeing polyester-based textiles.
　比較例２５～３０においては、色差△Ｅ（１００℃）及び染色速度変化率の少なくとも一つが不適であった。 In Comparative Examples 25-30, at least one of the color difference ΔE (100°C) and the rate of change in dyeing speed was unsuitable.
　比較例３１～３６においては、色差△Ｅ（１００℃）及び染色速度変化率の少なくとも一つが不適であった。 In Comparative Examples 31 to 36, at least one of the color difference ΔE (100°C) and the rate of change in dyeing speed was unsuitable.
　表１１は比較例３１～３６の結果を示す。このうち、比較例３１は前記式（Ｉ）で表されるキノン系赤色分散染料と前記式（ＸＩＩＩ）で表される難燃剤を併用して、比較例３２は前記式（ＩＩ）で表されるキノン系赤色分散染料と前記式（ＶＩＩＩ）で表される難燃剤を併用して、比較例３３は前記式（ＩＩＩ）で表されるキノン系赤色分散染料と前記式（Ｘ）で表される難燃剤を併用して、比較例３４は前記式（ＩＩＩ）で表されるキノン系赤色分散染料と前記式（ＸＩ）で表される難燃剤を併用して、比較例３５は前記式（ＩＶ）で表されるキノン系赤色分散染料と前記式（ＩＸ）で表される難燃剤を併用して、そして、比較例３６は前記式（ＩＶ）で表されるキノン系赤色分散染料と前記式（ＸＩ）で表される難燃剤を併用して、それぞれ、ポリエステル系繊維品を染色同時難燃加工した結果を示す。上記比較例３１～３６においては、いずれも、キノン系赤色分散染料は平均粒子径０．８μｍ、使用量は３．０％оｗｆであり、難燃剤は平均粒子径０．６μｍ、使用量は４．０％оｗｆである。 Table 11 shows the results of Comparative Examples 31-36. Among these, Comparative Example 31 uses a combination of the quinone red disperse dye represented by the formula (I) and the flame retardant represented by the formula (XIII), and Comparative Example 32 is represented by the formula (II). Using a combination of a quinone red disperse dye and a flame retardant represented by the formula (VIII), Comparative Example 33 is represented by the quinone red disperse dye represented by the formula (III) and the formula (X). Comparative Example 34 uses a combination of the quinone red disperse dye represented by the formula (III) and the flame retardant represented by the formula (XI), and Comparative Example 35 uses the formula ( IV) and the flame retardant represented by the formula (IX) are used in combination, and Comparative Example 36 uses the quinone red disperse dye represented by the formula (IV) and the above The flame retardants represented by the formula (XI) are used together to show the results of simultaneously dyeing and flame-retarding polyester textiles. In each of Comparative Examples 31 to 36, the quinone red disperse dye has an average particle size of 0.8 μm and the amount used is 3.0% wf, and the flame retardant has an average particle size of 0.6 μm and is used in an amount of 4 .0% owf.
　比較例３１～３６において、赤色分散染料と難燃剤の組み合わせは、この順序にて前述した比較例６、７、１５、１６、２０及び２２におけるそれらと対応しているが、赤色分散染料の使用量が比較例６、７、１５、１６、２０及び２２においては０．３％оｗｆ量であるところ、比較例３１～３６においては、３．０％оｗｆ量としたものであり、その結果、色差△Ｅ（１００℃）、△Ｅ（１３０℃）及び染色速度変化率の少なくとも１つにおいて不適である。 In Comparative Examples 31-36, the combinations of red disperse dye and flame retardant correspond to those in Comparative Examples 6, 7, 15, 16, 20 and 22 previously described in that order, but the use of red disperse dye While the amount was 0.3% in Comparative Examples 6, 7, 15, 16, 20 and 22, it was 3.0% in Comparative Examples 31 to 36. As a result, At least one of color difference ΔE (100° C.), ΔE (130° C.) and dyeing speed change rate is unsuitable.
　即ち、前記式（ＶＩＩＩ）、（ＩＸ）、（Ｘ）、（ＸＩ）及び（ＸＩＩＩ）で表される難燃剤は、比較例６、７、１５、１６、２０及び２２にみられるように、これと併用する赤色分散染料の使用量が少ないとき（０．３％оｗｆ）は、色差△Ｅ（１００℃）、△Ｅ（１３０℃）及び染色速度変化率のいずれも適正であるが、しかし、併用する赤色分散染料の使用量が多いとき（３．０％оｗｆ）は、染色速度変化率が大きくなる。よって、前記式（ＶＩＩＩ）、（ＩＸ）、（Ｘ）、（ＸＩ）及び（ＸＩＩＩ）で表される難燃剤は、前記式（Ｉ）～（ＶＩ）で表される分散染料を用いるポリエステル系繊維品の染色同時難燃加工において、上記分散染料の染色再現性を阻害している。
 
 
  That is, the flame retardants represented by the formulas (VIII), (IX), (X), (XI) and (XIII) are, as seen in Comparative Examples 6, 7, 15, 16, 20 and 22, When the amount of the red disperse dye used in combination is small (0.3% wf), both the color difference ΔE (100°C), ΔE (130°C) and the rate of change in the dyeing speed are appropriate. When the red disperse dye used in combination is used in a large amount (3.0% wf), the rate of change in dyeing speed increases. Therefore, the flame retardants represented by formulas (VIII), (IX), (X), (XI) and (XIII) are polyester-based using disperse dyes represented by formulas (I) to (VI). In flame-retardant processing simultaneously with dyeing of textiles, the dyeing reproducibility of the above-mentioned disperse dyes is hindered.

Claims (10)

  1. （Ａ）（１）下記式（Ｉ）
    Figure JPOXMLDOC01-appb-C000001
      
    で表されるキノン系赤色分散染料、
    （２）下記式（ＩＩ）
    Figure JPOXMLDOC01-appb-C000002
      
    で表されるキノン系赤色分散染料、
    （３）下記式（ＩＩＩ）
    Figure JPOXMLDOC01-appb-C000003
      
    で表されるキノン系赤色分散染料、
    （４）下記式（ＩＶ）
    Figure JPOXMLDOC01-appb-C000004
      
    で表されるキノン系赤色分散染料、及び
    （５）下記式（Ｖ）
    Figure JPOXMLDOC01-appb-C000005
      
    で表されるキノン系赤色分散染料よりなる群から選ばれる少なくとも１種と、
    （Ｂ）下記式（ＶＩＩ）
    Figure JPOXMLDOC01-appb-C000006
      
    で表されるリン酸エステルアミドを含む加工浴中にポリエステル系繊維品を浸漬し、加熱するポリエステル系繊維品の染色同時難燃加工方法。     (A) (1) Formula (I) below
    Figure JPOXMLDOC01-appb-C000001
    A quinone-based red disperse dye represented by
    (2) Formula (II) below
    Figure JPOXMLDOC01-appb-C000002
    A quinone-based red disperse dye represented by
    (3) the following formula (III)
    Figure JPOXMLDOC01-appb-C000003
    A quinone-based red disperse dye represented by
    (4) Formula (IV) below
    Figure JPOXMLDOC01-appb-C000004
    and (5) a quinone-based red disperse dye represented by the following formula (V)
    Figure JPOXMLDOC01-appb-C000005
    At least one selected from the group consisting of quinone-based red disperse dyes represented by
    (B) Formula (VII) below
    Figure JPOXMLDOC01-appb-C000006
    A dyeing and simultaneous flame retardant treatment method for polyester textiles, comprising immersing polyester textiles in a processing bath containing a phosphoric acid ester amide represented by and heating.
  2. 　前記加工浴中にポリエステル系繊維品を浸漬し、１０５℃以上に加熱する請求項１に記載のポリエステル系繊維品の染色同時難燃加工方法。 The method for simultaneously dyeing and flame-retarding a polyester fiber product according to claim 1, wherein the polyester fiber product is immersed in the processing bath and heated to 105°C or higher.
  3. 　前記加工浴は前記式（Ｉ）から（Ｖ）で表されるキノン系赤色分散染料よりなる群から選ばれる少なくとも１種を濃度０．０５～５％оｗｆの範囲で有し、前記式（ＶＩＩ）で表されるリン酸エステルアミドを濃度０．５～１０％оｗｆの範囲で有する請求項１に記載のポリエステル系繊維品の染色同時難燃加工方法。 The processing bath contains at least one selected from the group consisting of quinone red disperse dyes represented by formulas (I) to (V) at a concentration range of 0.05 to 5% wf, and ) in a concentration range of 0.5 to 10%owf.
  4. 　前記式（Ｉ）から（Ｖ）で表されるキノン系赤色分散染料と前記式（ＶＩＩ）で表されるリン酸エステルアミドがいずれも、平均粒子径０．２～２．０μｍの範囲にあるものである請求項１に記載のポリエステル系繊維品の染色同時難燃加工方法。 Both the quinone-based red disperse dyes represented by formulas (I) to (V) and the phosphate ester amide represented by formula (VII) have an average particle size in the range of 0.2 to 2.0 μm. The flame-retardant treatment method at the same time as dyeing the polyester fiber product according to claim 1.
  5. 　請求項１に記載の前記式（Ｉ）から（Ｖ）で表されるキノン系赤色分散染料よりなる群から選ばれる少なくとも１種と前記式（ＶＩＩ）で表されるリン酸エステルアミドを含む染色難燃加工ポリエステル系繊維品。 Dyeing containing at least one selected from the group consisting of quinone red disperse dyes represented by the formulas (I) to (V) according to claim 1 and a phosphate ester amide represented by the formula (VII) Flame-retardant polyester fiber product.
  6. （Ａ）（１）下記式（Ｉ）
    Figure JPOXMLDOC01-appb-C000007
      
    で表されるキノン系赤色分散染料、
    （２）下記式（ＩＩ）
    Figure JPOXMLDOC01-appb-C000008
      
    で表されるキノン系赤色分散染料、
    （３）下記式（ＩＩＩ）
    Figure JPOXMLDOC01-appb-C000009
      
    で表されるキノン系赤色分散染料、
    （４）下記式（ＩＶ）
    Figure JPOXMLDOC01-appb-C000010
      
    で表されるキノン系赤色分散染料、及び
    （５）下記式（Ｖ）
    Figure JPOXMLDOC01-appb-C000011
      
    で表されるキノン系赤色分散染料よりなる群から選ばれる少なくとも１種、及び
    （Ｂ）下記式（ＶＩ）
    Figure JPOXMLDOC01-appb-C000012
      
    で表されるアゾ系赤色分散染料と、
    （Ｃ）下記式（ＶＩＩ）
    Figure JPOXMLDOC01-appb-C000013
      
    で表されるリン酸エステルアミドを含む加工浴中にポリエステル系繊維品を浸漬し、加熱するポリエステル系繊維品の染色同時難燃加工方法。     (A) (1) Formula (I) below
    Figure JPOXMLDOC01-appb-C000007
    A quinone-based red disperse dye represented by
    (2) Formula (II) below
    Figure JPOXMLDOC01-appb-C000008
    A quinone-based red disperse dye represented by
    (3) the following formula (III)
    Figure JPOXMLDOC01-appb-C000009
    A quinone-based red disperse dye represented by
    (4) Formula (IV) below
    Figure JPOXMLDOC01-appb-C000010
    and (5) a quinone-based red disperse dye represented by the following formula (V)
    Figure JPOXMLDOC01-appb-C000011
    At least one selected from the group consisting of quinone-based red disperse dyes represented by and (B) the following formula (VI)
    Figure JPOXMLDOC01-appb-C000012
    and an azo red disperse dye represented by
    (C) the following formula (VII)
    Figure JPOXMLDOC01-appb-C000013
    A dyeing and simultaneous flame retardant treatment method for polyester textiles, comprising immersing polyester textiles in a processing bath containing a phosphoric acid ester amide represented by and heating.
  7. 　前記加工浴中にポリエステル系繊維品を浸漬し、１０５℃以上に加熱する請求項６に記載のポリエステル系繊維品の染色同時難燃加工方法。 The method for simultaneously dyeing and flame-retarding a polyester fiber product according to claim 6, wherein the polyester fiber product is immersed in the processing bath and heated to 105°C or higher.
  8. 　前記加工浴は前記式（Ｉ）から（Ｖ）で表されるキノン系赤色分散染料よりなる群から選ばれる少なくとも１種及び前記式（ＶＩ）で表されるアゾ系赤色分散染料を合計濃度０．０５～５％оｗｆの範囲で有し、前記式（ＶＩＩ）で表されるリン酸エステルアミドを濃度０．５～１０％оｗｆの範囲で有する請求項６に記載のポリエステル系繊維品の染色同時難燃加工方法。 The processing bath contains at least one selected from the group consisting of quinone red disperse dyes represented by formulas (I) to (V) and an azo red disperse dye represented by formula (VI) at a total concentration of 0. 0.05 to 5% owf, and the dyeing of the polyester fiber product according to claim 6, which has the phosphoric ester amide represented by the formula (VII) in a concentration range of 0.5 to 10% owf. Simultaneous flame retardant processing method.
  9. 　前記式（Ｉ）から（Ｖ）で表されるキノン系赤色分散染料及び前記式（ＶＩ）で表されるアゾ系赤色分散染料と前記式（ＶＩＩ）で表されるリン酸エステルアミドがいずれも、平均粒子径０．２～２．０μｍの範囲にあるものである請求項６に記載のポリエステル系繊維品の染色同時難燃加工方法。 The quinone red disperse dye represented by the formulas (I) to (V), the azo red disperse dye represented by the formula (VI), and the phosphate ester amide represented by the formula (VII) are all 7. The method for simultaneously dyeing and flame-retarding polyester fiber products according to claim 6, wherein the average particle size is in the range of 0.2 to 2.0 μm.
  10. 　請求項６に記載の前記式（Ｉ）から（Ｖ）で表されるキノン系赤色分散染料よりなる群から選ばれる少なくとも１種及び前記式（ＶＩ）で表されるアゾ系赤色分散染料と前記式（ＶＩＩ）で表されるリン酸エステルアミドを含む染色難燃加工ポリエステル系繊維品。
     
          At least one selected from the group consisting of the quinone red disperse dyes represented by the formulas (I) to (V) according to claim 6 and the azo red disperse dye represented by the formula (VI); A dyed, flame-retardant polyester fiber product containing a phosphoric acid ester amide represented by formula (VII).
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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH04164969A (en) * 1990-10-30 1992-06-10 Nippon Kayaku Co Ltd Disperse dye composition and method of dyeing hydrophobic fiber
JP2009270213A (en) * 2008-05-02 2009-11-19 Nicca Chemical Co Ltd Flame-retardant finishing agent for polyester-based fiber, flame-retardant polyester-based fiber using the same, and method for producing the same
JP2012102444A (en) * 2010-11-12 2012-05-31 Daikyo Kagaku Kk Scouring agent composition for polyester-based fiber knit and scouring method using the same

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH04164969A (en) * 1990-10-30 1992-06-10 Nippon Kayaku Co Ltd Disperse dye composition and method of dyeing hydrophobic fiber
JP2009270213A (en) * 2008-05-02 2009-11-19 Nicca Chemical Co Ltd Flame-retardant finishing agent for polyester-based fiber, flame-retardant polyester-based fiber using the same, and method for producing the same
JP2012102444A (en) * 2010-11-12 2012-05-31 Daikyo Kagaku Kk Scouring agent composition for polyester-based fiber knit and scouring method using the same

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