JPS62253658A - Dyeing liquid and dyeing using same - Google Patents

Abstract

PURPOSE:To provide a dyeing liquid capable of clearly dyeing with outstanding uniform dyeability, light-fastness and fastness to laundering such textiles as of wool, silk, nylon, polyacrylic fiber, polyurethane fiber, etc., containing specific azo compound(s) in a liquid medium. CONSTITUTION:The objective dyeing liquid containing, in a liquid medium, at least one kind of coloring matter compound of formula I (Y is H, methyl, methoxy, acetylamino or nitro, forming, in some cases, a benzene ring together with the carbon atom at 3-site of the benzene ring B; X is acetyl, benzoyl, p-toluenesulfonyl, or 4-chloro-6-hydroxy-1,3,5-triazine-2-yl; M is alkali metal, ammonium or amine) (e.g. a compound of formula II). Using this liquid, such textile fibers as of wool, etc., or (non)woven fabrics and mixed (non)woven fabrics containing, respectively, such fibers will be dyed.

Description

Detailed Description of the Invention (Field of Industrial Application) The present invention relates to a thermally stable dyeing liquid and a dyeing method using the same, and in particular to wool, silk, nylon, polyacrylic fibers, polyurethane fibers. It has excellent level dyeing properties for fibers such as, woven fabrics or non-woven fabrics made of these fibers, or blended woven fabrics or blended non-woven fabrics made of these fibers and other fibers, and has excellent light fastness and washing fastness of dyed products. The present invention relates to a staining solution with extremely good staining properties and a staining method using the same.

(Prior art) Conventionally, fibers such as wool, silk, nylon, polyacrylic fibers, polyurethane fibers, woven or non-woven fabrics made of these fibers, or blended woven fabrics or blended non-woven fabrics made of these fibers and other fibers have been used. The fabric 11 is dyed using a dyeing solution in which a reactive dye or an acidic dye is dissolved in an aqueous medium, for example, by dyeing methods such as dip dyeing or badging. In particular, dyeing methods using acidic dyes require only one bath, and the dyeing process is simple, so dyeing can be done using relatively small-scale equipment, and is widely practiced in various places.

(Problems to be Solved by the Present Invention) However, when using a dyeing solution using an acidic dye that is currently commercially available, the properties that those skilled in the art particularly desire during the dyeing process or in the dyed product, namely (+) Excellent level dyeing properties for dyed products.

(2) The dye is thermally stable in an aqueous dyebath and has extremely good dissolution stability even at high concentrations.

(3) The light fastness and washing fastness of the dyed product should be sufficient for practical use.

There are very few things that have all these properties.

In addition, there are almost no dyeing solutions that have a good magenta color, which is suitable for color matching using subtractive color mixing.

Therefore, the purpose of the present invention is to solve the problems of level dyeing, color tone, problems in the dyeing process, and various fastnesses of dyed products in dyeing using a dyeing solution using conventional commercially available acid dyes as mentioned above. It is an object of the present invention to provide vine dyeing #i and a dyeing method using the same, which solves the problems that are not always satisfactory.

The first object of the present invention is achieved by the following invention.

(Means for Solving the Problems) That is, the present invention provides a dyeing liquid characterized by containing at least one persimmon of a dye compound represented by the following general formula (^) in the liquid medium, and the dyeing liquid. This is the dyeing method used.

In the formula, Y represents a hydrogen atom T-, a methyl group, a methoxy group, an acetylamino group, or a nitro group, and B may form a benzene ring together with the carbon atom at the 3-position of the benzene ring B. be. On the other hand, and a base selected from amines.

(Function) The compound represented by formula (A) used in the present invention is:
- Any compound may be used as long as it is included in general formula (A), but particularly preferred specific examples are shown below.

(X represents a 4-chloro-6-hydroxy-1,3,5-triazin-2-yl group. The same applies hereinafter) [M = H
N(CII2CII□011)3 ] These compounds can be synthesized by conventionally known methods.

The main feature of the dyeing liquid of the present invention is that it contains a dye compound represented by the above general formula (Δ) in the liquid medium, and the dye compound contained may be a single persimmon or a mixture of two or more types. .

The content of the compound represented by the general formula (^) 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, even light color dyeing is not affected Almost no coloring effect on dyed items can be expected, and the content is 30 nails! If it exceeds 11%, it is not preferable because the dissolution stability of the dye in the dye bath and the level dyeing property of the dyed product decrease.

The main medium for dissolving the compound represented by the general formula (A) is 5 water, but a mixed system of water and a water-soluble or hydrophobic organic solvent can improve dyeing workability and dyeing speed, etc. The preferred result is 1:t. Furthermore, in the case of the type of object to be dyed, for example, in the case of objects 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: C1-C4 alkyl alcohols 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, trimethylene glycol, and mono- or di-lower (1 to 4 carbon atoms) alkyl ethers: dimethylformamide, dimethylacetamide. Ketones or ketone alcohols such as acetone and diacetone alcohol; Ethers such as tetrahydrofuran and dioxane; Polyalkylene glycols such as polyethylene glycol and polypropylene glycol: glycerin; N-methyl-2-pyrrolidone; 1,3-dimethyl- 2-imidazolidinone: Alkanolamines such as triethanolamine, jetanolamine, and monoethanolamine; sulfolane and the like.

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

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

Moreover, it is preferable to adjust the pH of the staining solution to a range of 2 to 5.

The essential components of the dyeing solution used in the present invention are as described above, but in order to control the dyeing speed and dye dyeing rate, it is preferable to add water-soluble inorganic salts to the dyebath. (j!!Water) Sodium sulfate, sodium chloride, ammonium acetate, ammonium sulfate, etc., and their content is preferably in the range of 3 to 30% by weight of the dyeing solution.

In addition, various conventionally known pH adjusters, penetrants, antifoaming agents, bath softeners, solubilizers, reduction inhibitors, leveling agents,
A loosening agent, a carrier, a migration inhibitor, etc. can be added as necessary.

As a typical example, specifically, as a pH adjuster (
ice) ammonium acetate, sulfuric acid, ammonium sulfate, and urea as a dissolving agent. In addition, fatty acid salts, alkyl! Acid ester salt, alkylbenzene sulfonate, alkylnaphthalene sulfonate, dialkyl sulfosuccinate, alkyl phosphate ester salt, naphthalene sulfonic acid formalin condensate, boxoxyethylene alkyl sulfate ester salt, polyoxyethylene alkyl ether, polyoxyethylene Various anionic and nonionic surfactants such as alkylphenyl ether, polyoxyethylene fatty acid ester, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene alkylamine, glycerin fatty acid ester, oxyethylene oxybrobylene block polymer, etc. This is especially important.

As mentioned above, the dyeing solution of the present invention has problems with level dyeing, color tone, dyeing process problems, and various fastness of dyed products when dyeing with a dyeing solution using conventional commercially available acid dyes. Our goal was to simultaneously solve the problems that were not always satisfactory, and we arrived at this result after intensive study, paying particular attention to the structure of the dye.

The dyeing method of the present invention uses the dyeing liquid as described above to dye fibers such as wool, silk, nylon, polyacrylic fibers, polyurethane fibers, woven fabrics or non-woven fabrics containing these fibers, or fabrics made of these fibers and other fibers. It is applied to blended woven fabrics, blended nonwoven fabrics, and objects in shapes other than fibers by conventionally known dyeing methods such as dip dyeing, badging, and printing.

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

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

Example 1 (Preparation of staining solution) Anhydrous sodium sulfate 10 parts (No.
2) Pigment compound Tripartite urea
5 parts thiodiethylene glycol 5 parts anionic surfactant (dialkyl sulfosuccinate) 1 part water
80 parts The above-mentioned mixture was stirred for 3 hours, and the p)I was adjusted to 3 with sulfuric acid to obtain the staining solution (a) of the present invention.

Example 2 (staining solution made by W4) Anhydrous sodium carbonate 0.5 part (NO,
Pigment compound of 6) 5 parts triethylene glycol monobutyl 5 parts ether water 90 parts All the above ingredients were stirred for 3 hours, ii. Obtained.

Example 3 (Preparation of staining solution) Ammonium sulfate 5 parts (No.
7) Pigment compound 2 parts Nonionic surfactant 1 part (Product name: Carazol LT, manufactured by Dai-Kogyo; manufactured by LL) Water
93 parts All of the above components were stirred for 3 hours, and the pH was adjusted to about 5 with acetic acid to obtain a staining solution (c) of the present invention.

Comparative Example 1 (Preparation of staining solution) The dye compound of (No. 2) was mixed with C, 1, 8 cid Re.
A comparative staining solution (d) was obtained by performing the same treatment as in Example 1 except that d35 was used instead.

Comparative Example 2 (Preparation of staining solution) The dye compound of (No. 6) was mixed with C,1,^cid Re
A comparative staining solution (e) was obtained by carrying out the same treatment as in Example 2 except that d52 was used instead.

The staining solutions (I to H) of Examples and Comparative Examples were all 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 comparative dyeing solution (e) showed slight pigment decomposition.

Example 4 (Dyeing method) A wool cloth thoroughly scoured and impregnated with water was immersed in the dyeing solution (a) shown in Example 1 at a bath ratio of 1:50, and heated to 40°C. It was heated and left for 10 minutes. Thereafter, the temperature was gradually raised to the boiling point over a period of 60 minutes, and dyeing was continued for 45 minutes in that state. The dyed material was soaped and thoroughly washed repeatedly.

Example 5 (Dyeing method) A well prepared nylon cloth was bagged using the dyeing method 11i shown in Example 2 and steamed at 100° C. for 10 minutes. After staining, soaping treatment was performed and washing was repeated thoroughly.

Example 6 (Dyeing method) Thoroughly purified silk cloth impregnated with water was soaked in the dyeing solution (c) shown in Example 3 at a bath ratio of 1:50, and heated to 40°C. and left for 10 minutes. Thereafter, the sample was gradually warmed to 80° C. over a period of 30 minutes, and dyed in that state for 45 minutes. The dyed material was soaped and washed thoroughly.

Comparative Example 3 (Dyeing Method) A dyed product was obtained by performing the same treatment as in Example 4, except that the staining solution (A) was replaced with comparative staining* (D).

, Comparative Example 4 (Dyeing Power Method) A dyed product was obtained by performing the same treatment as in Example 5, except that the staining solution (B) was replaced with a comparative staining solution (E).

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

-YoΣ22J(-Tues b■4 0 0 0 0Tuesday example 2
〇〇 〇 〇Jōhō±600.00 Mosquito Example O△ Δ Δ Comparative Example A Δ
The evaluation and evaluation criteria for the x x O ■ table are shown below.

*1 Level dyeing property The dyeing was visually judged.

〇--No unevenness at all Δ・−・～・There is some unevenness.

*2 Light fastness Irradiation was performed using a xenon arc fade-o-meter C135 (manufactured by Atlas Corporation) at a black panel temperature of 63° C. for 50 hours.

The evaluation is based on the test piece (1 piece 31 according to the IE LAD color system)
Points on the coordinate system were determined using the conversion formula to b-umbrella, and the color difference (ΔEab*) between the two points between the irradiation chamber and the sample after irradiation was used.

〇--ΔEaM<5 8-・-5≦ΔEaM≦10 ×...-ΔEab book 〉10 *3 Washing resistance ♂ Fastness Washing machine using synthetic detergent New Bead (trade name - Kako Co., Ltd.) using a conventional method Washing was carried out 10 times, and evaluation was made using ΔEatl in the same manner as in the case of light fastness.

〇--ΔEab 5 △−−−−5≦ΔE ab*≦10 X −−−−ΔEab4+>10 *4 colors The dyed matter was judged at 1 sight.

0 --- Clear magenta color.

Δ−−・Slightly off the magenta color.

Herein-1: The present invention is continued using several dye compounds as representative examples.
IR1, f-h< Denka Gaya Shin [■1. All of the dye compounds exemplified above other than b showed excellent effects as in the examples.

(Effects) The dyeing solution of the present invention is thermally stable, and can be used to dye fibers such as wool, braid, nylon, polyacrylic fibers, polyurethane fibers, or woven fabrics containing these fibers. When dyeing non-woven fabrics or blended woven fabrics made of these AA fibers and other fibers, or blended non-woven fabrics or blended non-woven fabrics, the level dyeing property is higher than when dyeing solutions using conventional commercially available acid dyes are used. The dyed product has excellent light fastness and washing fastness.

Furthermore, the color tone of the dyed product is clear and suitable for color matching by mixing colors.

Patent applicant: Canon Co., Ltd. Procedure Nefu Seisho (self-motivated) October 2, 1986

Claims (4)

[Claims] (1) A staining liquid characterized by containing at least one dye compound represented by the following general formula (A) in a liquid medium. ▲There are mathematical formulas, chemical formulas, tables, etc.▼(A) [In the formula, Y represents a hydrogen atom, a methyl group, a methoxy group, an acetylamino group, or a nitro group, and B represents the benzene ring B's 3 It may also form a benzene ring with the carbon atom in position. On the other hand, and a base selected from amines. ) (2) The dyeing solution according to claim (1), which contains 3 to 30% by weight of a water-soluble inorganic salt based on the total weight of the dyeing solution. (3) A method for dyeing an object to be dyed, characterized in that the dyeing liquid contains at least one type of dye compound represented by the following general formula (A) in the liquid medium. ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (A) [In the formula, Y represents a hydrogen atom, a methyl group, a methoxy group, an acetylamino group, or a nitro group, and B represents the benzene ring B's 3 It may also form a benzene ring with the carbon atom in position. On the other hand, and a base selected from amines. ] (4) The object to be dyed is wool, silk, nylon, polyacrylic fiber, polyurethane fiber, woven fabric or non-woven fabric containing these fibers, or blended woven fabric or blended non-woven fabric consisting of these fibers and other fibers. A dyeing method according to claim (3).