Method for dyeing polyester textile products and simultaneously flame-retarding them

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 azo disperse dye and fire retardant phosphoric acid ester amide represented by formula (VIII), 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 azo disperse dye is small despite the presence of the fire retardant.

Description

[Technical Field]

[0001] The present invention relates to a method for simultaneously dyeing and flame-retarding polyester fiber products, more particularly to a method for simultaneously dyeing and flame-retarding polyester fiber products, which comprises immersing a polyester fiber product in a treatment bath containing a specific azo disperse dye and a specific flame retardant, heating the polyester fiber product, and thereby obtaining a dyed and flame-retardant polyester fiber product with good dye reproducibility.Furthermore, the present invention relates to the dyed and flame-retardant polyester fiber product thus obtained. [Background technology]

[0002] Azo disperse dyes are known to have poorer lightfastness than quinone disperse dyes, but have strong coloring power.

[0003] [ka] ,

[0004] The following formula (II)

[0005] [ka] ,

[0006] and the following formula (III):

[0007] [ka]

[0008] It is known that azo disperse dyes represented by the formula (I) can provide disperse dye compositions that are excellent in both coloring strength and lightfastness when combined with specific quinone disperse dyes (see Patent Document 1).

[0009] In addition, the following formula (IV)

[0010] [ka]

[0011] It is also known that azo disperse dyes represented by the following formula are suitable for dyeing polyester fiber products (see Patent Document 2).

[0012] On the other hand, quinone disperse dyes are generally known to give dyed products excellent in light fastness. Examples of such quinone disperse dyes include those represented by the following formula (V):

[0013] [ka]

[0014] a quinone-based disperse dye represented by The following formula (VI)

[0015] [ka]

[0016] A quinone-based disperse dye represented by the formula: The following formula (VII)

[0017] [ka]

[0018] Quinone-based disperse dyes represented by the following formula are known (see Patent Documents 1, 3 and 4).

[0019] Conventionally, when dyeing polyester-based textile products, it is common to use red, yellow, and blue disperse dyes as the three primary colors and mix them depending on the desired color tone. In such cases, when the dyeing characteristics of these red, yellow, and blue disperse dyes, particularly the dyeing speed, i.e., the rate of increase in dye absorption with increasing temperature during dyeing, are uniform, even if the dyeing conditions, for example, the dyeing temperature, fluctuate to a certain extent, the color tone of the resulting dyed product is not significantly affected. In other words, disperse dyes of the three primary colors having the same dyeing speed are excellent in dyeing reproducibility of polyester-based textile products.

[0020] On the other hand, when the dyeing rates of the disperse dyes of the three primary colors of red, yellow and blue are not uniform, even a slight change in the dyeing conditions will cause a large change in not only the color tone but also the color strength of the resulting dyed product.

[0021] Thus, when dyeing polyester-based textiles with disperse dyes, it is required that the dyeing speeds of the disperse dyes of the three primary colors, red, yellow, and blue, are uniform. Therefore, in order to dye polyester-based textiles with good dyeing reproducibility, it has been proposed to use a combination of disperse dyes of the three primary colors, red, yellow, and blue, each having a specific structure (see Patent Documents 4 and 5).

[0022] As in the dyeing of polyester-based textiles described above, when a polyester-based textile is immersed in a processing bath containing a yellow disperse dye, a red disperse dye, and a blue disperse dye together with a flame retardant, and heated to dye the polyester-based textile while simultaneously subjecting it to flame retardant processing using the flame retardant, depending on the flame retardant used, even when dyeing is performed under the same conditions, the dyeing speed of each of the disperse dyes may vary compared to when a polyester-based textile is dyed with a yellow disperse dye, a red disperse dye, and a blue disperse dye in the absence of a flame retardant, and the color tone and color density of the resulting dyed product may change significantly. As a result, it may not be possible to dye and flame-retardant polyester-based textiles simultaneously with good dyeing reproducibility.

[0023] Therefore, in order to dye polyester fiber products using yellow disperse dyes, red disperse dyes, and blue disperse dyes and simultaneously flame-retardant them to obtain flame-retardant dyed products with good dyeing reproducibility, not only must the dyes used have excellent dyeing reproducibility, but the flame retardants used must also not inhibit the excellent dyeing reproducibility of the disperse dyes used in combination. [Prior art documents] [Patent documents]

[0024] [Patent Document 1] Patent Publication No. 9-176509 [Patent Document 2] Tokko No. 1966-5468 [Patent Document 3] Patent Publication No. 32-9089 [Patent Document 4] Patent Publication No. 2004-168950 [Patent Document 5] WO2012 / 067027A1 Summary of the Invention [Problem to be solved by the invention]

[0025] The present invention aims to provide a method for simultaneously dyeing and flame-retarding polyester fiber products, which uses at least one azo disperse dye selected from the azo disperse dyes represented by the formulas (I) to (IV), or at least one azo disperse dye selected from the azo disperse dyes represented by the formulas (I) to (IV) and at least one quinone disperse dye selected from the quinone disperse dyes represented by the formulas (V) to (VII), in addition to a specific flame retardant, to obtain dyed and flame-retardant polyester fiber products with good dyeing reproducibility.

[0026] A further object of the present invention is to provide a dyed and flame-retardant polyester fiber product obtained by the above-mentioned method for simultaneous dyeing and flame-retardant treatment. [Means for solving the problem]

[0027] According to the present invention, (A)(1) Formula (I) below

[0028] [ka]

[0029] an azo disperse dye represented by (2) Formula (II) below

[0030] [ka]

[0031] an azo disperse dye represented by (3) Formula (III)

[0032] [ka]

[0033] Azo disperse dyes represented by the formula: (4) Formula (IV)

[0034] [ka]

[0035] At least one azo disperse dye selected from the group consisting of: (B) Formula (VIII) below

[0036] [ka]

[0037] The present invention provides a method for simultaneously dyeing and flame-retarding polyester fiber articles, which comprises immersing the polyester fiber articles in a treatment bath containing a phosphoric acid ester amide represented by the formula (I) and heating the bath.

[0038] Hereinafter, in the present invention, the above method may be referred to as the first method.

[0039] Furthermore, according to the present invention, at least one kind selected from the group consisting of azo disperse dyes represented by the above formulas (I) to (IV), The following formula (V)

[0040] [ka]

[0041] a quinone-based disperse dye represented by The following formula (VI)

[0042] [ka]

[0043] A quinone-based disperse dye represented by the formula: The following formula (VII)

[0044] [ka]

[0045] and a phosphoric acid ester amide represented by formula (VIII).

[0046] Hereinafter, in the present invention, the above method may be referred to as the second method.

[0047] In the first method according to the present invention, more specifically, a polyester fiber product is immersed in the processing bath and heated to 105°C or higher, and the processing bath preferably contains at least one azo disperse dye represented by any one of the formulas (I) to (IV) in a concentration ranging from 0.05 to 5% by weight, and a phosphoric acid ester amide represented by the formula (VIII) in a concentration ranging from 0.5 to 10% by weight.

[0048] In the second method according to the present invention, more specifically, a polyester fiber product is immersed in the processing bath and heated to 105°C or higher, and the processing bath preferably contains at least one azo disperse dye represented by the above formulas (I) to (IV) and at least one quinone disperse dye represented by the above formulas (V) to (VII) in a total concentration ranging from 0.05 to 5% by weight, and contains the phosphoric acid ester amide represented by the above formula (VIII) in a concentration ranging from 0.5 to 10% by weight.

[0049] Furthermore, according to the present invention, it is preferable that the azo-based and quinone-based disperse dyes and the phosphoric acid ester amide used have an average particle size in the range of 0.2 to 2.0 μm.

[0050] The method for simultaneously dyeing and flame-retarding polyester fiber products according to the present invention comprises the steps of: At least one selected from the group consisting of azo disperse dyes represented by the formulas (I) to (IV), or At least one selected from the group consisting of azo disperse dyes represented by the formulas (I) to (IV) and at least one selected from the group consisting of quinone disperse dyes represented by the formulas (V) to (VII). This method is used to dye polyester textiles and simultaneously apply flame retardant treatment to them. [Effects of the Invention]

[0051] Conventionally, when a polyester fiber product is dyed and flame-retarded at the same time using a processing bath containing a known flame retardant and an azo disperse dye, the dyeing rate of the azo disperse dye changes significantly compared to when the azo disperse dye is used in the absence of the flame retardant, making it impossible to obtain a dyed and flame-retardant polyester fiber product with good dyeing reproducibility.

[0052] However, according to the present invention, when a polyester fiber product is dyed and flame-retarded in a processing bath containing, together with the flame-retardant phosphate ester amide represented by formula (VIII), at least one selected from the group consisting of azo disperse dyes represented by formulas (I) to (IV), or at least one selected from the group consisting of azo disperse dyes represented by formulas (I) to (IV) and at least one selected from the group consisting of quinone disperse dyes represented by formulas (V) to (VII), the change in the dyeing speed of the azo disperse dye is small, and when the quinone disperse dye is used in combination, the change in the dyeing speed of both the azo disperse dye and the quinone disperse dye is small, so that dyed and flame-retardant polyester fiber products can be obtained with good dyeing reproducibility. DETAILED DESCRIPTION OF THE INVENTION

[0053] The method for simultaneously dyeing and flame-retarding polyester fiber products according to the present invention comprises immersing a polyester fiber product in a treatment bath containing at least one selected from the group consisting of azo disperse dyes represented by the formulas (I) to (IV) above, or at least one selected from the group consisting of azo disperse dyes represented by the formulas (I) to (IV) above, at least one selected from the group consisting of quinone disperse dyes represented by the formulas (V) to (VII) above, and a phosphoric acid ester amide represented by the formula (VIII) above, followed by heating to perform simultaneously dyeing and flame-retarding. This method allows for the production of dyed and flame-retardant polyester fiber products with good dyeing reproducibility.

[0054] That is, the method for simultaneously dyeing and flame-retarding polyester fiber products according to the present invention comprises, in a processing bath, at least one dye selected from the group consisting of azo disperse dyes represented by the formulas (I) to (IV), or at least one dye selected from the group consisting of azo disperse dyes represented by the formulas (I) to (IV), at least one dye selected from the group consisting of quinone disperse dyes represented by the formulas (V) to (VII), and the phosphoric acid ester amide represented by the formula (VIII).

[0055] The azo disperse dyes represented by the above formulas (I) to (IV) are all already known, and commercially available products can be used in the method of the present invention.

[0056] The azo disperse dye represented by the above formula (I) is CI Disperse Yellow 163.

[0057] The azo disperse dye represented by the above formula (II) is CI Disperse Red 167:1, the azo disperse dye represented by the above formula (III) is CI Disperse Blue 165, and the azo disperse dye represented by the above formula (IV) is CI Disperse Blue 79:1.

[0058] Furthermore, the quinone disperse dye represented by the formula (V) is CI Disperse Blue 56, the quinone disperse dye represented by the formula (VI) is CI Disperse Blue 60, and the quinone disperse dye represented by the formula (VII) is CI Disperse Blue 77.

[0059] In the present invention, when a polyester fiber product is subjected to simultaneous dyeing and flame retardancy treatment using the azo disperse dye or the azo disperse dye and quinone disperse dye together with the flame retardant phosphate ester amide, it is preferable that both the disperse dye and the flame retardant phosphate ester amide have an average particle size of 0.2 to 2.0 μm so that the disperse dye and the flame retardant phosphate ester amide can sufficiently diffuse and adhere to the interior of the polyester fiber product. However, it is not necessary for the disperse dye and the flame retardant phosphate ester amide to have the same average particle size.

[0060] The disperse dye and phosphoric acid ester amide having an average particle size within the above-mentioned range can be obtained, for example, by previously pulverizing the system disperse dye and phosphoric acid ester amide, respectively, in water containing a surfactant using a sand mill or a ball mill.

[0061] Preferred examples of surfactants used when micronizing the azo disperse dyes and quinone disperse dyes include anionic surfactants such as formalin condensates of naphthalenesulfonic acid and alkylbenzenesulfonic acid, formalin condensates of naphthalenesulfonic acid, formalin condensates of cresol and 2-naphthol-6-sulfonic acid, formalin condensates of alkylnaphthalenesulfonic acid, formalin condensates of creosote oil sulfonic acid, and ligninsulfonic acid; nonionic surfactants such as block copolymers of ethylene oxide and propylene oxide, ethylene oxide adducts of alkylphenols, and ethylene oxide adducts of polystyrenated phenols; and mixtures of these anionic surfactants with nonionic surfactants.

[0062] Preferred surfactants used in micronizing the phosphoric acid ester amide include, for example, anionic surfactants such as sulfate salts of arylated phenol ethylene oxide adducts and sulfosuccinate salts of styrenated phenol ethylene oxide adducts; nonionic surfactants such as block copolymers of ethylene oxide and propylene oxide, ethylene oxide adducts of alkylphenols, and ethylene oxide adducts of polystyrenated phenols; and mixtures of these anionic surfactants and nonionic surfactants.

[0063] As described above, the method for simultaneously dyeing and flame-retarding polyester fiber products according to the present invention involves wet-grinding a specific azo disperse dye, and, when used in combination with an azo disperse dye, a specific quinone disperse dye and a specific flame retardant, respectively, in the presence of the surfactant to obtain dispersions containing fine particles of the disperse dye and flame retardant, which are then added to a bath containing water to form a processing bath having a predetermined bath ratio. Polyester fiber products are immersed in this processing bath and subjected to in-bath exhaust treatment at a temperature of 105°C or higher, preferably 105 to 140°C, and particularly preferably 110 to 140°C, for 30 to 60 minutes. Thereafter, the polyester fiber products thus treated are removed from the processing bath, soaped, washed with water, and then dehydrated and dried to obtain dyed and flame-retardant processed polyester fiber products.

[0064] In the present invention, for example, when a polyester fiber product is immersed in a processing bath in a jet dyeing machine and heated to 105°C or higher for in-bath exhaustion treatment, the pressure in the dyeing machine is usually in the range of 0.1 to 0.5 MPa.

[0065] In this way, according to the present invention, when the azo disperse dye or the quinone disperse dye is used in combination, a polyester fiber product can be obtained that is dyed with the azo disperse dye and the quinone disperse dye and is flame-retarded with the flame retardant.

[0066] In the first method according to the present invention, the amounts of the azo disperse dye and the flame retardant phosphate ester amide used are not particularly limited, but the amount of the azo disperse dye used is usually in the range of 0.05 to 5% owf, preferably in the range of 0.1 to 5% owf, and more preferably in the range of 0.3 to 3.0% owf.

[0067] In the second method according to the present invention, when the quinone disperse dye is used in combination with the azo disperse dye, the total amount of the azo disperse dye and the quinone disperse dye used is usually in the range of 0.05 to 5% owf, preferably in the range of 0.1 to 5% owf, and more preferably in the range of 0.3 to 3.0% owf.

[0068] In addition, the amount of the flame retardant phosphate ester amide used is usually preferably in the range of 0.5 to 10% owf, more preferably in the range of 0.5 to 8.0% owf, and most preferably in the range of 1.0 to 8.0% owf, in order to impart sufficient flame retardancy to the polyester fiber product to be dyed.

[0069] The bath ratio of the processing bath is not particularly limited, but is usually in the range of 1:3 to 1:30, and preferably in the range of 1:5 to 1:20. If the bath ratio is lower than 1:3, the polyester fiber product may not be sufficiently immersed in the processing bath, resulting in uneven dyeing, while if it is higher than 1:30, the amount of water used for simultaneous dyeing and flame retardancy processing becomes unnecessarily large, which is uneconomical.

[0070] In the method of the present invention, the polyester-based fiber product refers to fibers containing at least polyester fibers and fabrics containing such fibers, such as yarn, cotton, woven fabric, and nonwoven fabric, and preferably refers to polyester fibers and fabrics made thereof, such as yarn, cotton, woven fabric, and nonwoven fabric. Furthermore, fabrics such as woven fabrics and nonwoven fabrics may be single-layered or laminated with two or more layers, or may be composites made of yarn, cotton, woven fabric, nonwoven fabric, etc.

[0071] In the present invention, the polyester fiber may be, for example, polyethylene terephthalate, polypropylene terephthalate, polybutylene terephthalate, polyethylene naphthalate, polybutylene naphthalate, polyethylene terephthalate / isophthalate, polyethylene terephthalate / 5-sulfoisophthalate, polyethylene terephthalate / polyoxybenzoyl, polybutylene terephthalate / isophthalate, poly(D-lactic acid), poly(L-lactic acid), a copolymer of D-lactic acid and L-lactic acid, a copolymer of D-lactic acid and aliphatic hydroxycarboxylic acid, a copolymer of L-lactic acid and aliphatic hydroxycarboxylic acid, or a copolymer of L-lactic acid and aliphatic hydroxycarboxylic acid. Examples of the copolymer include copolymers of aliphatic hydroxycarboxylic acids with hydroxycarboxylic acids, polycaprolactones such as poly-ε-caprolactone (PCL), polyaliphatic hydroxycarboxylic acids such as polymalic acid, polyhydroxycarboxylic butyric acid, polyhydroxyvaleric acid, and β-hydroxybutyric acid (3HB)-3-hydroxyvaleric acid (3HV) random copolymers, and polyesters of glycols and aliphatic dicarboxylic acids such as polyethylene succinate (PES), polybutylene succinate (PBS), polybutylene adipate, and polybutylene succinate-adipate copolymers, but are not limited to these examples.

[0072] The dyed and flame-retardant polyester fiber products obtained by the method of the present invention are suitable for use in, for example, seats, seat covers, curtains, wallpaper, ceiling cloth, carpets, drop curtains, construction protection sheets, tents, canvas, etc.

[0073] In the method of the present invention, other conventionally known disperse dyes can be used in combination as long as the dyeing reproducibility of the method of simultaneously dyeing and flame-retarding polyester fiber products according to the present invention is not impaired. Examples of such disperse dyes include, but are not limited to, red disperse dyes such as CI Disperse Red 53, 60, 86, and 92, yellow disperse dyes such as CI Disperse Yellow 71, 42, 51, and CI Solvent Yellow 163, blue disperse dyes such as CI Disperse Blue 54, and orange disperse dyes such as CI Disperse Orange 29 and 155. [Example]

[0074] The present invention will be described in detail below with reference to examples and comparative examples, but the present invention is not limited to these examples in any way.

[0075] (Average particle size of azo disperse dyes, quinone disperse dyes, and flame retardants) In the following, the azo disperse dye, quinone disperse dye, and flame retardant were all wet-ground in the presence of a surfactant using a mill filled with glass beads having a diameter of 0.5 mm to have a predetermined average particle size, and then used as an aqueous dispersion.

[0076] The average particle diameters of the azo disperse dyes, quinone disperse dyes, and flame retardants are all volume-based median diameters determined based on particle size distribution measurements of the respective dispersions using a laser diffraction particle size distribution analyzer, SALD-2000J, manufactured by Shimadzu Corporation.

[0077] (Color measurement of dyed materials) In the following, the color of the obtained dyed product was measured using a spectrophotometer CM-600d (manufactured by Konica Minolta, Inc.).

[0078] In the following examples and comparative examples, first, polyester double pique (basis weight 240 g / m 2 ) was used as the treated fabric, and a dyed product obtained by dyeing this fabric with a disperse dye in the absence of a flame retardant at a temperature of 100°C and a dyed product obtained by dyeing this fabric with the same disperse dye as above in the presence of a flame retardant were measured for each of the dyed products, and the color difference ΔE(100°C) between these dyed products was determined. Also, a dyed product obtained by dyeing the treated 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 this fabric with the same disperse dye as above in the presence of a flame retardant were measured for each of the dyed products, and the color difference ΔE(130°C) between these dyed products was determined.

[0079] Next, the color difference ΔE (dye) of the dyed fabric obtained by dyeing with disperse dye at temperatures of 100°C and 130°C in the absence of a flame retardant, and the color difference ΔE (dye + flame retardant) of the dyed fabric obtained by dyeing with disperse dye at temperatures of 100°C and 130°C in the presence of a flame retardant were calculated.

[0080] Next, the value of the formula (ΔE(dye) / ΔE(dye+flame retardant)) × 100 was calculated from the color difference ΔE(dye) and the color difference ΔE(dye+flame retardant), and this value was used as the rate of change in dyeing speed when the treated fabric was dyed with a disperse dye in the presence of a flame retardant.

[0081] In the present invention, as will be described later, the dyeing reproducibility is deemed to be excellent when all of the values ​​of ΔE(100°C), ΔE(130°C) and (ΔE(dye) / ΔE(dye+flame retardant))×100, i.e., the dyeing speed change rate, are within a certain range.

[0082] In the present invention, when evaluating the color tone of the dyed product obtained by simultaneously dyeing and flame-retarding the treated fabric, the L * a * b * The color space is based on the color system. * a * b* In the color system, L * The value is called the brightness index, and the larger the value, the brighter it is, and the smaller the value, the darker it is. * The value is 100, and the black L * The value is 0. * value and b * The values ​​represent hue and saturation and are called chromatic indices. * The more positive the value, the more reddish the color becomes, and the more negative the value, the more greenish the color becomes. * The more positive the value, the more yellowish the color becomes, and the more negative the value, the more blueish the color becomes.

[0083] Such a L * a * b * In the color system, the difference between two colors, i.e., the color difference ΔE, is expressed as the distance between the coordinates of the two colors in the color space. △E=[(△L * ) 2 +(△a * ) 2 +(△b * ) 2 ] 1 / 2

[0084] Example 1 The fabric to be treated (polyester double pique (basis weight 240 g / m)) was added to a processing bath containing 0.3% owf of an azo disperse dye having an average particle size of 0.8 μm represented by the formula (I) at a bath ratio of 1:10. 2 )) was added, and the temperature was raised from 40°C to 100°C at a rate of 2°C per minute, followed by an in-bath exhaust treatment, followed by a soaping treatment and a water washing treatment, followed by dehydration and drying to obtain a dyed fabric. The dyed fabric was measured and the L * (100), a * (100) and b * (100) was sought.

[0085] Next, the same fabric to be treated as above was placed in a processing bath with the same composition as above, and the temperature was raised from 40°C to 130°C at a rate of 2°C per minute, and the bath was maintained at that temperature for 30 minutes to carry out an exhaustion treatment in the bath, followed by a soaping treatment and a water washing treatment, followed by dehydration and drying to obtain a dyed fabric. The dyed fabric was measured in the same manner as above to obtain a L * (130), a * (130) and b * (130) was sought.

[0086] Separately, the same fabric to be treated as above was placed in a processing bath containing 0.3% owf of an azo disperse dye having an average particle size of 0.8 μm and represented by the formula (I) above and 4.0% owf of a flame retardant phosphoric acid ester amide having an average particle size of 0.6 μm and represented by the formula (VIII) above at a bath ratio of 1:10, and the bath was heated from 40°C to 100°C at a heating rate of 2°C per minute to perform an exhaustion treatment in the bath, followed by a soaping treatment and a water washing treatment, followed by dehydration and drying to obtain a dyed fabric.

[0087] The dyed fabric was measured in the same manner as above to obtain the L * (100 flame retardant), a * (100 flame retardant) and b * (100 flame retardant).

[0088] Next, the same fabric to be treated as above was placed in a processing bath with the same composition as above, and the temperature was raised from 40°C to 130°C at a rate of 2°C per minute, and the bath was maintained at that temperature for 30 minutes to carry out an exhaustion treatment in the bath, followed by a soaping treatment and a water washing treatment, followed by dehydration and drying to obtain a dyed fabric. The dyed fabric was measured in the same manner as above to obtain a L * (130 flame retardant), a * (130 flame retardants) and b * (130 Flame Retardant).

[0089] Based on the color measurement results thus obtained, the following values ​​were calculated.

[0090] (1) The color difference ΔE(100°C) between the dyed fabric obtained by dyeing the treated fabric with the disperse dye in the absence of the flame retardant at 100°C and the dyed fabric obtained by dyeing the treated fabric with the disperse dye in the presence of the flame retardant is calculated by the formula: △E(100℃)=[(L * (100)-L * (100% flame retardant) 2 +(a * (100)-a * (100% flame retardant) 2 +(b * (100)-b * (100% flame retardant) 2 ] 1 / 2 was obtained from.

[0091] (2) The color difference ΔE(130°C) between the dyed fabric obtained by dyeing the treated fabric with the disperse dye in the absence of the flame retardant at 130°C and the dyed fabric obtained by dyeing the treated fabric with the disperse dye in the presence of the flame retardant is calculated by the formula: △E(130℃)=[(L * (130)-L * (130 Flame retardant) 2 +(a * (130)-a * (130 Flame retardant) 2 +(b * (130)-b * (130 Flame retardant) 2 ] 1 / 2 was obtained from.

[0092] (3) The color difference ΔE (dye) between the dyed fabric obtained by dyeing the treated fabric with the disperse dye at 100°C in the absence of the flame retardant and the dyed fabric obtained by dyeing the treated fabric at 130°C is calculated by the formula △E(dye)=[(L * (100)-L * (130) 2 +(a * (100)-a * (130) 2 +(b * (100)-b * (130) 2 ] 1 / 2 was obtained from.

[0093] (4) The color difference ΔE (dye + flame retardant) between the dyed fabric obtained by dyeing the treated fabric with the disperse dye at 100°C in the presence of the flame retardant and the dyed fabric obtained by dyeing the treated fabric at 130°C was calculated using 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 was obtained from. was obtained from.

[0094] Next, as described above, the following formula (△E(dye) / △E(dye + flame retardant)) x 100 The value obtained by the above procedure was taken as the rate of change in the dyeing speed of the disperse dye when the flame retardant was added to a processing bath containing the disperse dye.

[0095] (evaluation) The evaluation criteria for ΔE (100°C), ΔE (130°C) and the rate of change in dyeing speed are as follows:

[0096] △E (100℃) was rated as ◯ (suitable) if it was less than 5.00, and × (unsuitable) if it was 5.00 or more. △E (130℃) was rated as ◯ (suitable) if it was less than 5.00, and × (unsuitable) if it was 5.00 or more.

[0097] The value of the dyeing speed change rate exceeds 100 when ΔE (dye) is greater than ΔE (dye + flame retardant). In other words, it can be said that the dyeing speed has increased by using a flame retardant in combination with a disperse dye. When ΔE (dye) is smaller than ΔE (dye + flame retardant), the value is 100 or less. In other words, it can be said that the dyeing speed has decreased by using a flame retardant in combination with a disperse dye, and therefore it can be said that the flame retardant has inhibited the dye absorption.

[0098] If the dyeing speed is too fast, uneven dyeing occurs, and if it is too slow, poor color development occurs. Therefore, in the present invention, when the dyeing speed change rate is in the range of 120 to 100, it is evaluated as ◯ (suitable), and when it is less than 100 or is 121 or more, it is evaluated as × (unsuitable).

[0099] Examples 2 to 4 In Example 1, a dyed fabric was obtained in the same manner as in Example 1, except that the azo disperse dye represented by the formula (I) and having an average particle size of 0.8 μm was replaced with the azo disperse dyes represented by the formulas (II) to (IV), each having an average particle size of 0.8 μm.

[0100] The dyed fabric was subjected to color measurement in the same manner as in Example 1 to determine ΔE (100°C), ΔE (130°C) and the rate of change in dyeing speed. The evaluation results of Examples 1 to 4 are shown in Table 1.

[0101] Examples 5 to 8 In Examples 1 to 4, dyed fabrics were obtained in the same manner, except that 3.0% owf of azo disperse dyes each having an average particle size of 0.8 μm and represented by the formula (I) to (IV) were used instead of 0.3% owf of azo disperse dye having an average particle size of 0.8 μm and represented by the formula (I).

[0102] The dyed fabric was subjected to color measurement in the same manner as in Example 1 to determine ΔE (100°C), ΔE (130°C) and the rate of change in dyeing speed. The evaluation results of Examples 5 to 8 are shown in Table 2.

[0103] Examples 9 to 12 In Examples 1 to 4, dyed fabrics were obtained in the same manner as in Examples 1 to 4, except that 8.0% owf of flame retardant phosphate ester amide having an average particle size of 0.6 μm represented by the formula (VIII) was used instead of 4.0% owf of flame retardant phosphate ester amide having an average particle size of 0.6 μm represented by the formula (VIII). Azo disperse dyes each having an average particle size of 0.8 μm represented by the formulas (I) to (IV) were used at 0.3% owf.

[0104] The dyed fabric was subjected to color measurement in the same manner as in Example 1 to determine ΔE (100°C), ΔE (130°C) and the rate of change in dyeing speed. The evaluation results of Examples 9 to 12 are shown in Table 3.

[0105] Examples 13 to 16 In Examples 1 to 4, dyed fabrics were obtained in the same manner as in Examples 1 to 4, except that 1.0% owf of a flame retardant phosphate ester amide having an average particle size of 0.6 μm represented by the formula (VIII) was used instead of 4.0% owf of a flame retardant phosphate ester amide having an average particle size of 0.6 μm represented by the formula (VIII). 0.3% owf of azo disperse dyes each having an average particle size of 0.8 μm represented by the formulas (I) to (IV) were used.

[0106] The dyed fabric was subjected to color measurement to determine ΔE(100°C), ΔE(130°C) and the rate of change in dyeing speed in the same manner as in Example 1. The evaluation results of Examples 13 to 16 are shown in Table 4.

[0107] Examples 17 to 19 In Example 1, a dyed fabric was obtained in the same manner as in Example 1, except that either an azo disperse dye having an average particle size of 0.8 μm and represented by the formula (III) above or a quinone disperse dye having an average particle size of 0.8 μm and represented by the formulas (V) to (VII) above was used as the disperse dye.

[0108] The dyed fabric was subjected to color measurement to determine ΔE (100°C), ΔE (130°C) and the rate of change in dyeing speed in the same manner as in Example 1. The evaluation results of Examples 17 to 19 are shown in Table 5.

[0109] Comparative Example 1 In Example 1, instead of the flame retardant phosphate ester amide represented by the formula (VIII), a flame retardant having an average particle size of 0.6 μm and represented by the following formula (IX) was used.

[0110] [ka]

[0111] A dyed fabric was obtained in the same manner as above, except that resorcinol bis(2,6-dixylenyl phosphate) represented by the following formula was used.

[0112] Comparative Example 2 In Example 1, instead of the flame retardant phosphate ester amide represented by the formula (VIII), a flame retardant having an average particle size of 0.6 μm and represented by the following formula (X) was used.

[0113] [ka]

[0114] A dyed fabric was obtained in the same manner as above, except that 10-benzyl-9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide represented by the following formula was used.

[0115] Comparative Example 3 In Example 1, instead of the flame retardant phosphate ester amide represented by the formula (VIII), a flame retardant having an average particle size of 0.6 μm and represented by the following formula (XI) was used.

[0116] [ka]

[0117] A dyed fabric was obtained in the same manner as above, except that 2-phenoxyethyl diphenyl phosphate represented by the following formula was used.

[0118] Comparative Example 4 In Example 1, instead of the flame retardant phosphate ester amide represented by the formula (VIII), a flame retardant having an average particle size of 0.6 μm and represented by the following formula (XII) was used.

[0119] [ka]

[0120] A dyed fabric was obtained in the same manner as above, except that 5,5-dimethyl-2-(2'-phenylphenoxy)-1,3,2-dioxaphosphorinane-2-oxide represented by the following formula was used.

[0121] Comparative Example 5 In Example 1, instead of the flame retardant phosphate ester amide represented by the formula (VIII), a flame retardant having an average particle size of 0.6 μm and represented by the following formula (XIII) was used.

[0122] [ka]

[0123] A dyed fabric was obtained in the same manner as above, except that p-cresyl phosphate represented by the following formula was used.

[0124] Comparative Example 6 In Example 1, instead of the flame retardant phosphate ester amide represented by the formula (VIII), a flame retardant having an average particle size of 0.6 μm and represented by the following formula (XIV) was used.

[0125] [ka]

[0126] A dyed fabric was obtained in the same manner as above, except that tris(2,3-dibromopropyl)isocyanurate represented by the following formula was used.

[0127] The dyed fabrics obtained in the above Comparative Examples 1 to 6 were subjected to colorimetry in the same manner as in Example 1 to determine ΔE(100°C), ΔE(130°C) and the rate of change in dyeing speed. The evaluation results for Comparative Examples 1 to 6 are shown in Table 6.

[0128] Comparative Examples 7 to 12 Dyed fabrics were obtained in the same manner as in Comparative Examples 1 to 6, except that the azo disperse dye represented by formula (I) was replaced with the azo disperse dye represented by formula (II).

[0129] The dyed fabric was subjected to color measurement in the same manner as in Example 1 to determine ΔE (100°C), ΔE (130°C) and the rate of change in dyeing speed. The evaluation results of Comparative Examples 7 to 12 are shown in Table 7.

[0130] Comparative Examples 13 to 18 Dyed fabrics were obtained in the same manner as in Comparative Examples 1 to 6, except that the azo disperse dye represented by formula (I) was replaced with the azo disperse dye represented by formula (III).

[0131] The dyed fabric was subjected to color measurement in the same manner as in Example 1 to determine ΔE(100°C), ΔE(130°C) and the rate of change in dyeing speed. The evaluation results of Comparative Examples 13 to 18 are shown in Table 8.

[0132] Comparative Examples 19 to 24 Dyed fabrics were obtained in the same manner as in Comparative Examples 1 to 6, except that the azo disperse dye represented by formula (I) was replaced with the azo disperse dye represented by formula (IV).

[0133] The dyed fabric was subjected to color measurement in the same manner as in Example 1 to determine ΔE (100°C), ΔE (130°C) and the rate of change in dyeing speed. The evaluation results of Comparative Examples 19 to 24 are shown in Table 9.

[0134] Comparative Example 25 A dyed fabric was obtained in the same manner as in Example 1, except that 3.0% owf of an azo disperse dye represented by formula (I) and having an average particle size of 0.8 μm was used, and resorcinol bis(2,6-dixylenyl phosphate) represented by formula (IX) and having an average particle size of 0.6 μm was used instead of the flame retardant represented by formula (VIII).

[0135] Comparative Example 26 In Example 1, a dyed fabric was obtained in the same manner as above, except that in place of the azo disperse dye represented by formula (I), 3.0% owf of an azo disperse dye represented by formula (III) having an average particle size of 0.8 μm was used, and in place of the flame retardant represented by formula (VIII), 5,5-dimethyl-2-(2'-phenylphenoxy)-1,3,2-dioxaphosphorinane-2-oxide represented by formula (XII) having an average particle size of 0.6 μm was used.

[0136] Comparative Example 27 A dyed fabric was obtained in the same manner as in Example 1, except that in place of the azo disperse dye represented by formula (I), 3.0% owf of an azo disperse dye represented by formula (III) having an average particle size of 0.8 μm was used, and in place of the flame retardant represented by formula (VIII), tris(2,3-dibromopropyl) isocyanurate represented by formula (XIV) having an average particle size of 0.6 μm was used.

[0137] Comparative Example 28 In Example 1, the azo disperse dye represented by formula (I) was replaced with the azo disperse dye represented by formula (XV)

[0138] [ka]

[0139] A dyed fabric was obtained in the same manner, except that an azo disperse dye having an average particle size of 0.8 μm represented by the formula (XV) was used. The azo disperse dye represented by the formula (XV) is CI Disperse Red 258, which is not an azo disperse dye specified for use in the present invention.

[0140] The dyed fabrics obtained in the above Comparative Examples 25 to 28 were colorimetrically 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. The evaluation results of Comparative Examples 25 to 28 are shown in Table 10.

[0141] [Table 1]

[0142] Table 2

[0143] Table 3

[0144] Table 4

[0145] Table 5

[0146] Table 6

[0147] Table 7

[0148] Table 8

[0149] Table 9

[0150] Table 10

[0151] Table 1 shows that when any of the disperse dyes represented by the formulas (I) to (IV) is used in an amount of 0.3% by weight in the presence of a flame retardant represented by the formula (VIII) in an amount of 4.0% by weight to dye a treated fabric made of polyester fiber, both the color differences ΔE(100°C) and ΔE(130°C) are small and appropriate, and the rate of change in dyeing speed is also appropriate.

[0152] That is, at 100°C and 130°C, there is a small color difference between the dyed fabric obtained by dyeing a treated fabric with a disperse dye represented by each of the formulas (I) to (IV) in the absence of the flame retardant represented by formula (VIII) and the dyed fabric obtained by dyeing a treated fabric with the disperse dye in the presence of the flame retardant, and further, the aforementioned rate of change in dyeing rate is appropriate. Therefore, even when the flame retardant is used in combination with the disperse dye, the rate of change in dyeing rate is smaller than when the disperse dye is used in the absence of the flame retardant.

[0153] Table 2 shows that when any of the disperse dyes represented by the formulas (I) to (IV) is used in an amount of 3.0% by weight in the presence of a flame retardant represented by the formula (VIII) in an amount of 4.0% by weight at 100°C and 130°C, the color differences ΔE(100°C) and ΔE(130°C) obtained are both small and appropriate, and the rate of change in dyeing speed is also appropriate.

[0154] Table 3 shows that when any of the disperse dyes represented by the formulas (I) to (IV) is used in an amount of 0.3% by weight in the presence of the flame retardant represented by the formula (VIII) in an amount of 8.0% by weight at 100°C and 130°C, the color differences ΔE(100°C) and ΔE(130°C) obtained are both small and appropriate, and the rate of change in dyeing speed is also appropriate.

[0155] Table 4 shows that when any of the disperse dyes represented by the formulas (I) to (IV) is used in an amount of 0.3% by weight in the presence of 1.0% by weight of the flame retardant represented by the formula (VIII) at 100°C and 130°C, the color differences ΔE(100°C) and ΔE(130°C) obtained are both small and appropriate, and the rate of change in dyeing speed is also appropriate.

[0156] Table 5 shows that at 100°C and 130°C, when 0.3% of the disperse dye represented by the formula (III) or 0.3% of the disperse dye represented by the formulas (V) to (VII) is used in the presence of 4.0% of the flame retardant represented by the formula (VIII), the dyed products obtained have small and appropriate color differences ΔE(100°C) and ΔE(130°C), and the rate of change in dyeing speed is also appropriate.

[0157] As described above, according to the present invention, a method for simultaneously dyeing and flame-retarding polyester textiles, in which polyester textiles are immersed in a bath containing at least one azo disperse dye selected from the group consisting of azo disperse dyes represented by formulas (I) to (IV) and a flame-retardant phosphate ester amide represented by formula (VIII), and then heated, results in small and appropriate color differences ΔE(100°C) and ΔE(130°C), as well as appropriate dyeing rate change rates, even when the treated fabric is subjected to simultaneously dyeing and flame-retarding treatment at temperatures of 100°C and 130°C, and the amounts of the azo disperse dye and flame-retardant used are varied, compared to when polyester textiles are dyed with an azo disperse dye in the absence of a flame retardant. Thus, according to the present invention, polyester textiles can be subjected to simultaneously dyeing and flame-retarding treatment with good dyeing reproducibility.

[0158] In accordance with the present invention, a method for simultaneously dyeing and flame-retarding polyester textiles is performed by immersing and heating a polyester textile in a bath containing at least one azo disperse dye selected from the group consisting of formulas (I) to (IV) and at least one quinone disperse dye selected from the group consisting of formulas (V) to (VII) and a flame-retardant phosphate ester amide selected from the group consisting of formula (VIII). Compared with dyeing polyester textiles with the azo disperse dye and the quinone disperse dye in the absence of a flame retardant, the color differences ΔE(100°C) and ΔE(130°C) are both small and appropriate, and the dyeing rate change rate is also appropriate. Thus, the present invention enables simultaneously dyeing and flame-retarding polyester textiles with good dyeing reproducibility.

[0159] In contrast, Table 6 shows the results of dyeing polyester textiles using the azo disperse dye represented by formula (I) in the presence of conventionally known representative flame retardants represented by formulas (IX) to (XIV) instead of the flame retardant represented by formula (VIII). In Comparative Examples 2 to 6, at least one of the color difference ΔE (100°C) and the rate of change in dyeing speed was unsatisfactory, but in Comparative Example 1, all of the color difference ΔE (100°C), ΔE (130°C), and the rate of change in dyeing speed were appropriate. Separate results for Comparative Example 1 will be shown later.

[0160] Similarly, Table 7 shows the results of dyeing polyester fiber products in Comparative Examples 7 to 12 using the azo disperse dye represented by formula (II) in the presence of conventionally known representative flame retardants represented by formulas (IX) to (XIV) instead of the flame retardant represented by formula (VIII).

[0161] In Comparative Examples 7 to 12, at least one of the color difference ΔE (100° C.) and the rate of change in dyeing speed was inadequate.

[0162] Table 8 shows the results of dyeing polyester fiber products in Comparative Examples 13 to 18 using the azo disperse dye represented by formula (III) in the presence of conventionally known representative flame retardants represented by formulas (IX) to (XIV) instead of the flame retardant represented by formula (VIII).

[0163] In Comparative Examples 13, 14, 15, and 17, at least one of the color difference ΔE (100°C) and the rate of change in dyeing speed was inadequate, but in Comparative Examples 16 and 18, all of the color difference ΔE (100°C), ΔE (130°C), and the rate of change in dyeing speed were appropriate. Separate results for Comparative Examples 16 and 18 will be shown later.

[0164] Table 9 shows the results of dyeing polyester fiber products in Comparative Examples 19 to 24 using the azo disperse dye represented by formula (IV) in the presence of conventionally known representative flame retardants represented by formulas (IX) to (XIV) instead of the flame retardant represented by formula (VIII).

[0165] In Comparative Examples 19 to 24, at least one of the color difference ΔE (100° C.) and the rate of change in dyeing speed was unsuitable.

[0166] Table 10 shows the results of Comparative Examples 25 to 28. Comparative Example 25 uses a disperse dye represented by formula (I) in combination with a flame retardant represented by formula (IX). Comparative Example 26 uses a disperse dye represented by formula (III) in combination with a flame retardant represented by formula (XII). Comparative Example 27 uses a disperse dye represented by formula (III) in combination with a flame retardant represented by formula (XIV). In all Comparative Examples 25 to 27, the disperse dye had an average particle size of 0.8 μm and was used in an amount of 3.0% owf. The flame retardant had an average particle size of 0.6 μm and was used in an amount of 4.0% owf.

[0167] In Comparative Examples 25 to 27, the combinations of azo disperse dyes and flame retardants correspond to those in Comparative Examples 1, 16, and 18 described above, but the amount of azo disperse dye used was 0.3% owf in Comparative Examples 1, 16, and 18, while it was 3.0% owf in Comparative Examples 25 to 27. As a result, at least one of the color difference ΔE(100°C), ΔE(130°C), and dyeing speed change rate was inappropriate.

[0168] That is, as seen in Comparative Examples 1, 16, and 18, the flame retardants represented by the formulas (IX), (XII), and (XIV) exhibited appropriate color differences ΔE(100°C), ΔE(130°C), and dyeing speed change rates when the amount of azo disperse dye used in combination with the flame retardant was small (0.3% owf), but the dyeing speed change rate increased when the amount of azo disperse dye used in combination with the flame retardant was large (3.0% owf). Thus, the flame retardants represented by the formulas (IX), (XII), and (XIV) inhibited the dyeing reproducibility of the disperse dye in the simultaneous dyeing and flame-retardant treatment of polyester fiber products using the disperse dyes represented by the formulas (I) to (IV).

[0169] Comparative Example 28 shows the results of simultaneously dyeing and flame-retarding a polyester fiber product in the same manner as in Example 1, except that the azo disperse dye represented by the formula (I) in Example 1 was replaced with the azo disperse dye represented by the formula (XV). However, the rate of change in dyeing speed was too large and inappropriate.

Claims

1. (A) (1) Formula (I) 【Chemistry 1】 an azo disperse dye represented by (2) Formula (II) below 【Chemistry 2】 an azo disperse dye represented by (3) Formula (III): 【Transformation 3】 Azo disperse dyes represented by the formula: (4) Formula (IV) 【Chemistry 4】 and at least one azo disperse dye selected from the group consisting of: (B) a compound represented by the following formula (VIII): 【Transformation 5】 and heating the polyester fiber product in a temperature range of 105°C to 140°C, in which the color difference and the rate of change in dyeing rate are small compared to those in the case of dyeing in the absence of the phosphoric acid ester amide.

2. 2. The method for simultaneously dyeing and flame-retarding polyester fiber products according to claim 1, wherein the processing bath contains at least one of the azo disperse dyes represented by formulas (I) to (IV) in a concentration ranging from 0.05 to 5% owf, and the phosphoric acid ester amide represented by formula (VIII) in a concentration ranging from 0.5 to 10% owf.

3. The method for simultaneously dyeing and flame-retarding polyester fiber products according to claim 1, wherein the azo disperse dyes represented by formulas (I) to (IV) and the phosphoric acid ester amide represented by formula (VIII) both have an average particle size in the range of 0.2 to 2.0 μm.

4. (A) (1) A compound represented by the following formula (I): 【Chemistry 1】 an azo disperse dye represented by (2) Formula (II) below 【Chemistry 2】 an azo disperse dye represented by (3) Formula (III): 【Transformation 3】 Azo disperse dyes represented by the formula: (4) Formula (IV): 【Chemistry 4】 and at least one azo disperse dye selected from the group consisting of: (B) a compound represented by the following formula (VIII): 【Transformation 5】 A dyed flame-retardant polyester fiber product containing a phosphoric acid ester amide represented by the formula:

5. (A) (1) Formula (I) 【Transformation 6】 an azo disperse dye represented by (2) Formula (II) below 【Transformation 7】 an azo disperse dye represented by (3) Formula (III): 【Transformation 8】 Azo disperse dyes represented by the formula: (4) Formula (IV) 【Chemistry 9】 and at least one azo disperse dye selected from the group consisting of: (B) (1) Formula (V) below 【Chemistry 10】 a quinone-based disperse dye represented by (2) Formula (VI) below 【Chemistry 11】 A quinone-based disperse dye represented by the formula: (3) Formula (VII) 【Chemistry 12】 At least one quinone-based disperse dye selected from the quinone-based disperse dyes represented by the formula: (C) a compound represented by the following formula (VIII): 【Chemistry 13】 and heating the polyester fiber product in a temperature range of 105°C to 140°C, in which the color difference and the rate of change in dyeing rate are small compared to those in the case of dyeing in the absence of the phosphoric acid ester amide.

6. 6. The method for simultaneously dyeing and flame-retarding polyester fiber products according to claim 5, wherein the processing bath contains at least one azo disperse dye represented by formulas (I) to (IV) and at least one quinone disperse dye represented by formulas (V) to (VII) in a total concentration ranging from 0.05 to 5% owf, and contains the phosphoric acid ester amide represented by formula (VIII) in a concentration ranging from 0.5 to 10% owf.

7. The method for simultaneously dyeing and flame-retarding polyester fiber products according to claim 5, wherein the azo disperse dyes represented by formulas (I) to (IV), the quinone disperse dyes represented by formulas (V) to (VII), and the phosphoric acid ester amide represented by formula (VIII) all have an average particle size in the range of 0.2 to 2.0 μm.

8. (A) (1) A compound represented by the following formula (I): 【Transformation 6】 an azo disperse dye represented by (2) Formula (II) below 【Transformation 7】 an azo disperse dye represented by (3) Formula (III): 【Transformation 8】 Azo disperse dyes represented by the formula: (4) Formula (IV) 【Chemistry 9】 and at least one azo disperse dye selected from the group consisting of: (B) (1) Formula (V) below 【Chemistry 10】 a quinone-based disperse dye represented by (2) Formula (VI) below 【Chemistry 11】 A quinone-based disperse dye represented by the formula: (3) Formula (VII) 【Chemistry 12】 At least one quinone-based disperse dye selected from the quinone-based disperse dyes represented by the formula: (C) a compound represented by the following formula (VIII): 【Chemistry 13】 A dyed flame-retardant polyester fiber product containing a phosphoric acid ester amide represented by the formula:

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