JPH0670310B2 - Dyeing method and dyed product obtained by the method - Google Patents

Description

Description: TECHNICAL FIELD The present invention relates to a thermally stable dyeing method and a dyed product obtained by the method, and in particular to wool, silk, nylon, polyacrylic fibers, and polyurethane. Fibers such as system fibers or woven or non-woven fabrics made of these fibers, or mixed spun woven fabrics or non-woven spun fabrics made of these fibers and other fibers, have excellent levelness, and light fastness and resistance to dyeing The present invention relates to a dyeing method having extremely good fastness to washing and a dyed product obtained by the method.

(Prior Art) Conventionally, fibers such as wool, silk, nylon, polyacrylic fibers, polyurethane fibers, etc., or woven fabrics or nonwoven fabrics made of these fibers, or mixed-spun woven fabrics or mixed-spun nonwoven fabrics made of these fibers and other fibers. The dyeing is carried out with a dyeing solution in which a reactive dye or an acid dye is dissolved in an aqueous medium, for example, a dyeing method such as dip dyeing or padding treatment. In particular, the dyeing method using an acid dye can be dyed with a relatively small-scale facility because dyeing can be done in one bath and the dyeing process is simple, and is widely used in various places.

(Problems to be Solved by the Present Invention) However, when a dyeing solution using an acid dye that is currently on the market is used, the properties that a person skilled in the art particularly desires during the dyeing process or the dyed product, that is, (1) Excellent levelness of dyed products.

(2) The dye is thermally stable in the aqueous dyebath and has very good dissolution stability even at a high concentration.

(3) The dyed product should have a lightfastness and a washfastness that can withstand practical levels.

Those equipped with all of the above properties are extremely limited.
In addition, when a dyeing solution having a good magenta color suitable for a dyeing method by color mixing of dyes, so-called subtractive color mixing, there is almost no state.

Therefore, the object of the present invention is not always the problem of level dyeability in dyeing with a dyeing solution using a conventional commercially available acid dye as described above, a problem of color tone, a problem in the dyeing process, and various fastnesses of the dyed product. It is an object of the present invention to provide a dyeing method and a dyed product obtained by the method, which can simultaneously solve the problem of being unsatisfactory.

Such an object of the present invention is achieved by the following present invention.

(Means for Solving Problems) That is, the present invention relates to wool, silk, nylon, polyacrylic fibers or polyurethane fibers, woven or non-woven fabrics containing these fibers, or blended fibers containing these fibers and other fibers. A dyeing method characterized by dyeing a woven fabric or a mixed-spun non-woven fabric with a dyeing solution containing at least one kind of a dye compound represented by the following general formula (A) in a liquid medium, and a dyed product obtained by the method. is there.

(In the formula, Y represents any one of a hydrogen atom, a methyl group, a methoxy group, an acetylamino group, and a nitro group, and may form a benzene ring together with the carbon atom at the 3-position of the benzene ring B. X is an acetyl group, a benzoyl group, a paratoluenesulfonyl group, 4-chloro-6-hydroxy-1,3,5-
Represents any of triazin-2-yl groups, and M represents
It is a base selected from alkali metals, ammonium and amines. (Operation) The compound represented by the general formula (A) used in the present invention may be any compound as long as it is included in the general formula (A), but particularly preferred specific examples are shown below.

(X is 4-chloro-6-hydroxy-1,3,5-triazine-2-
Represents an yl group. The same applies below) These compounds can be synthesized by a conventionally known method.

The dyeing solution used in the present invention is mainly characterized in that it contains a dye compound represented by the above general formula (A) in a liquid medium, and the dye compound contained is one kind or a mixture of two or more kinds. But it's okay.

The content of the compound represented by the general formula (A) in the total amount of the dyeing solution is preferably 0.01 to 30% by weight. When the content is less than 0.01% by weight, almost no coloring effect can be expected on the object to be dyed even with light color dyeing, and when the content exceeds 30% by weight, the stability of the dye in the dye bath is considered to be stable. It is not preferable because the levelness of the dyed product is lowered.

Water is mainly used as a medium for dissolving the compound represented by the general formula (A), but when a mixed system of water and a water-soluble or hydrophobic organic solvent is used, dyeing workability and dyeing speed are improved. In this respect, preferable results can be obtained. Further, in the case of the type of the article to be dyed, for example, the article to be dyed other than fibers such as synthetic resin filaments and molded articles, a water-soluble or hydrophobic organic solvent may be mainly used.

Examples of suitable water-soluble organic solvents used in combination here include alkyl alcohols having 1 to 4 carbon atoms such as methyl alcohol, ethyl alcohol, propyl alcohol, and butyl alcohol; tetrahydrofurfuryl alcohol; ethylene glycol, diethylene glycol, triethylene. Glycols such as glycol, tetraethylene glycol, propylene glycol, dipropylene glycol, thiodiethylene glycol, hexylene glycol and trimethylene glycol and their mono- or di-lower (C1-4) alkyl ethers; dimethylformamide, dimethylacetamides; Ketones or ketone alcohols such as acetone and diacetone alcohol; ethers such as tetrahydrofuran and dioxane; polyethylene glycol, Polyalkylene glycols such as polypropylene glycol; glycerin; N-methyl-2-pyrrolidone; 1,3-dimethyl-2-imidazolidinone; alkanolamines such as triethanolamine, diethanolamine, monoethanolamine; sulfolane, etc. is there.

The content of these water-soluble organic solvents in the liquid medium is
Generally, it is desirable that the content is 1 to 50% by weight, preferably 5 to 40%, and more preferably 10 to 30%.

The content of water is preferably in the range of 50 to 95% by weight.

The pH of the dyeing solution is preferably adjusted within the range of 2-5.

The essential components of the dyeing solution used in the present invention are as described above, but it is preferable to add a water-soluble inorganic salt to the dyeing bath in order to control the dyeing speed and the dyeing rate. Specifically, it is (anhydrous) sodium sulfate, sodium chloride, ammonium acetate, ammonium sulfate and the like, and the content thereof is preferably in the range of 3 to 30% by weight of the dyeing solution.

Further, in addition, various conventionally known pH adjusting agents, penetrants, defoamers, bath softeners, solubilizers, reduction inhibitors, leveling agents, slow-dyeing agents, carriers, migration inhibitors, etc. may be added as necessary. Can be added.

Typical examples include (ice) acetic acid, ammonium acetate, sulfuric acid, ammonium sulfate as a pH adjusting agent, and urea as a dissolving agent. In addition, fatty acid salts, alkyl sulfate ester salts, alkylbenzene sulfonates, alkylnaphthalene sulfonates, dialkyl sulfosuccinates, which also have the effects of penetration, level dyeing, and slowing agents,
Alkyl phosphate ester salt, naphthalene sulfonic acid formalin condensate, polyoxyethylene alkyl sulfate ester salt, polyoxyethylene alkyl ether, polyoxyethylene alkylphenyl ether, polyoxyethylene fatty acid ester, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester , Polyoxyethylene alkylamine, glycerin fatty acid ester,
Various anionic and nonionic surfactants such as oxyethylene oxypropylene block polymers are particularly important.

As described above, the dyeing solution used in the present invention is a level dyeing problem in dyeing with a dyeing solution using a conventional commercial acid dye, a problem of color tone, a problem in a dyeing process, various fastnesses of dyed products. With the desire to be able to solve the problem that is not always satisfied at the same time, the present invention has been achieved as a result of diligent study focusing on the structure of the dye.

The dyeing method of the present invention comprises fibers such as wool, silk, nylon, polyacrylic fibers and polyurethane fibers, or woven or non-woven fabrics containing these fibers, or these fibers and other fibers, in the dyeing method of the present invention. It is carried out by applying a conventionally known dyeing method, for example, dip dyeing, padding treatment, textile printing, etc., to a mixed-spun woven fabric or a mixed-spun nonwoven fabric, and further to shaped articles other than fibers.

The temperature at the time of dyeing, for example, the temperature of the dyeing bath and padding bath, etc., is set to be optimal depending on the conditions such as dyeing concentration, type of dye, type of material to be dyed, pH of the bath, etc. In this case, further, for example, a dyeing treatment by a steaming method, an HT steaming method, a thermofix method, or a thermosol method is performed, and then an undyed dye is removed by a known washing treatment such as soaping. Further, in some cases, it is subjected to a fixing treatment to obtain a final dyed product.

Next, the present invention will be described more specifically with reference to Examples and Comparative Examples. In the text, parts are based on weight unless otherwise specified.

Example 1 (Preparation of dyeing solution) Anhydrous sodium sulfate 10 parts (No. 2) pigment compound 3 parts Urine 5 parts Thiodiethylene glycol 5 parts Anionic surfactant (dialkylsulfosuccinate) 1 part Water 80 parts All of the above The components were stirred for 3 hours and adjusted to pH 3 with sulfuric acid to obtain a dyeing solution (a) used in the present invention.

Example 2 (Preparation of dyeing solution) 0.5 part of anhydrous sodium carbonate (No. 6) 5 parts triethylene glycol monobutyl ether 5 parts water 90 parts All the above components were stirred for 3 hours, and the pH became 3.5 with acetic acid. Thus, a staining solution (b) used in the present invention was obtained.

Example 3 (Preparation of dyeing solution) Ammonium sulfate 5 parts (No.7) dye compound 2 parts Nonionic surfactant 1 part (trade name; Carazol LT, manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd.) Water 93 parts The mixture was stirred for a period of time, and the pH was adjusted to about 5 with acetic acid to obtain a dyeing solution (C) used in the present invention.

Comparative Example 1 (Preparation of Dyeing Solution) The same treatment as in Example 1 was carried out except that the dye compound of (No. 2) was replaced with CI Acid Red 35 to obtain a dyeing solution for comparison (d).

Comparative Example 2 (Preparation of Dyeing Solution) The same treatment as in Example 2 was carried out except that the dye compound of (No. 6) was replaced with CI Acid Red 52 to obtain a dyeing solution for comparison (e).

The dyeing solutions (a-e) of Examples and Comparative Examples were both uniform solutions. In order to compare the thermal stability of these dyeing solutions, when they were stored in an oven at 60 ° C. for one month, only the dyeing solution for comparison (e) slightly decomposed the dye.

Example 4 (Dyeing method) A wool cloth impregnated with water and impregnated with the dyeing solution (a) shown in Example 1 was soaked in a bath ratio (1:50),
It was heated to 40 ° C and left for 10 minutes. After that, the temperature was gradually raised to the boiling point in 60 minutes, and dyeing was performed in that state for 45 minutes. The dyed product was soaped and thoroughly washed.

Example 5 (Dyeing method) A fully scoured nylon cloth was padded with the dyeing solution (b) shown in Example 2 and steamed at 100 ° C for 10 minutes. After dyeing, soaping treatment was performed and washing was sufficiently repeated.

Example 6 (Dyeing method) A silk cloth thoroughly scoured and impregnated with the dyeing solution (C) shown in Example 3 was dipped in a bath ratio (1:50) to give 40
It was heated to ℃ and left for 10 minutes. 80 ° C gradually over the next 30 minutes
The temperature was raised up to and dyeing was performed for 45 minutes in that state. The dyed product was soaped and thoroughly washed.

Comparative Example 3 (Dyeing method) A dyed product was obtained by performing the same treatment as in Example 4 except that the dyeing solution (a) was replaced with the dyeing solution for comparison (d).

Comparative Example 4 (Dyeing method) A dyed product was obtained by the same treatment as in Example 5 except that the dyeing solution (b) was replaced with the comparative dyeing solution (e).

Table 1 shows the properties of the dyed products obtained in Examples (4 to 6) and Comparative Examples (3 to 4).

The present invention has been described above by using several examples of the dye compounds as representative examples, but all of the above-exemplified dye compounds other than those used in the examples exhibited the same excellent effects as in the case of the examples.

(Effect) The dyeing solution used in the present invention is thermally stable, and using this dyeing solution, fibers such as wool, silk, nylon, polyacrylic fibers, polyurethane fibers, or woven fabrics containing these fibers are used. When dyeing a non-woven fabric or a mixed-spun woven fabric or a mixed-spun nonwoven fabric or a mixed-spun nonwoven fabric composed of these fibers and other fibers, the leveling property is higher than that in the case where a dyeing solution using a conventional commercially available acid dye is used. It is also excellent in light fastness and wash fastness. Further, the color tone of the dyed product is also clear, which is suitable for color matching by color mixing.

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁵ Identification number Office reference number FI technical display location D06P 3/74 9356-4H (56) Reference JP-A-59-131657 (JP, A) JP JP-A-57-187358 (JP, A) JP-A-51-149983 (JP, A) JP-A-59-75950 (JP, A) JP-A-60-58958 (JP, A) JP-A-59-78273 (JP , A) JP 60-81250 (JP, A) JP 61-241370 (JP, A)

Claims (2)

[Claims] 1. A wool, silk, nylon, polyacrylic fiber or polyurethane fiber, or a woven or non-woven fabric containing these fibers, or a mixed spun woven fabric or a mixed spun non-woven fabric composed of these fibers and other fibers, represented by the following general formula: A dyeing method comprising dyeing with a dyeing solution containing at least one of the dye compounds represented by (A) in a liquid medium. (In the formula, Y represents any one of a hydrogen atom, a methyl group, a methoxy group, an acetylamino group, and a nitro group, and may form a benzene ring together with the carbon atom at the 3-position of the benzene ring B. X is an acetyl group, a benzoyl group, a paratoluenesulfonyl group, 4-chloro-6-hydroxy-1,3,5-
Represents any of triazin-2-yl groups, and M represents
It is a base selected from alkali metals, ammonium and amines. ) " 2. Wool, silk, nylon, polyacrylic fibers or polyurethane fibers, woven or non-woven fabrics containing these fibers, or a mixed spun woven fabric or a non-woven spun fabric composed of these fibers and other fibers is represented by the following general formula: A dyed product characterized by being dyed with a dye compound represented by (A). (In the formula, Y represents any one of a hydrogen atom, a methyl group, a methoxy group, an acetylamino group, and a nitro group, and may form a benzene ring together with the carbon atom at the 3-position of the benzene ring B. X is an acetyl group, a benzoyl group, a paratoluenesulfonyl group, 4-chloro-6-hydroxy-1,3,5-
Represents any of triazin-2-yl groups, and M represents
It is a base selected from alkali metals, ammonium and amines. )