JPS62253659A - 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 textile fibers 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 [Y1 is H, halogen, alkyl, alkoxy, nitro, alkyl sulfonylamino, aryl sulfonylamino, triazinylamino, acylamino, -COOM, or -SO3M; Y2 is H or -SO3M; M is alkali metal, ammonium or amine; Q is (substituted) phenyl or naphthyl; n is 1-3; W is Cu, Co, or Ni; where, in said Q, azo group and -O- group are at ortho-sites each other] (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 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, V-fiber, polyurethane. It has excellent level dyeing properties for fibers such as polyester fibers, woven fabrics or non-woven fabrics made of these fibers, or warm-spun woven fabrics or blended non-woven fabrics made of these fibers and other fibers, and also has excellent light fastness and durability of dyed products. The present invention relates to a dyeing solution with extremely good washing fastness and a dyeing method using the same.

(Prior art) Conventionally, fibers such as wool, silk, nylon, polyacrylic fibers, polyurethane fibers, woven fabrics or non-woven fabrics made of these fibers, or warm-spun woven fabrics or blended non-woven fabrics made of these fibers and other fibers have been used. Dyeing is carried out 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 a bath for dyeing, and the dyeing process is simple, so dyeing can be carried out using relatively small-scale equipment, and is widely practiced overseas.

(Problems to be Solved by the Present Invention) However, when using a dyeing solution using an acidic dye that is currently commercially available, those skilled in the art will not be able to find the properties that are particularly desired during the dyeing process or for the dyed product, that is, ( 1) Excellent level dyeing properties for dyed objects.

(2) The dye is thermally stable in the aqueous dyebath, and
- The dissolution stability is extremely good even at a concentration of 5.

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

Those that have all the measurement properties J1 are extremely limited. 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 objectives of the present invention are to solve the problem of level dyeing, the problem of color tone, the problem of dyeing and fabrication in dyeing using a dyeing solution using conventional commercially available acid dyes as described in -. It is an object of the present invention to provide a vine dyeing solution and a dyeing method using the same, which solves the problem that various fastnesses are not necessarily satisfactory.

These objects of the present invention are achieved by the following invention.

(First Step for Solving the Problems) That is, the present invention provides a staining liquid characterized by containing at least one type of dye compound represented by the following general formula (8) in a liquid medium, and the staining liquid. This is a dyeing method that uses

(However, Y in the above formula is hydrogen atom f, halogen atom, alkyl group, alkoxy group, nitro group, alkylsulfonylamino group, arylsulfonylamino group, triazinylamino group, acylamino group, -(:OOM JI
ll, or -5o3- group, Q represents a phenyl group or naphthyl J^ which may be substituted with an alkoxy group, an acylamino group, a hydroxyl group, or a trianidylamino group, and n
represents 1.2 or 3, M represents an alkali metal, ammonium or amines, W represents (:u, Go
, represents Ni. However, in Q, the azo group and the 10-group are located at the ortho position. ) (Function) The compound represented by the general formula (A) used in the present invention is:
Any compound may be used as long as it is included in general formula (8), but particularly preferred specific examples are shown below.

1'1aula 5t13Na compound l

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

Containment of the compound represented by general formula (8) in the total amount of staining solution! The content of No. 11 is preferably 0.01 to 30% by weight. When the Jil content is less than 0.01% by weight, almost no coloring effect can be expected on the dyed object even in light color dyeing, and when the Jil content exceeds 30% by weight, the dissolution of the dye in the dye bath becomes unstable. It is not preferable because it reduces the quality and level dyeing property of the dyed product.

Water is the main medium for dissolving the compound represented by the direct formula (A), but a mixed system of water and a water-soluble or hydrophobic organic solvent improves dyeing workability and dyeing speed. Favorable results are obtained in terms of rings. 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: 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, trimethylene glycol, and their 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 gellicols such as polyethylene glycol 5 polypropylene glycol: glycerin; N-methyl-2-pyrrolidone; 1,3-dimethyl- 2-imidazolidinone; alkanolamines such as triethanolamine, jetanolamine, and monoethanolamine; and sulfolane.

Containment of these water-soluble organic solvents in the liquid medium! 11
is generally 1 to 50% in ton%f%, preferably ! ,
, -+ 1st 17/. , preferably 10 to 30
% range [preferably within the river.

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

Further, the pH of the staining solution is preferably adjusted to a range of 2 to 5: J4.

Although the essential components of the dyeing solution used in the present invention are as described above, it is preferable to add water-soluble inorganic salts to the dyebath in order to control the dyeing speed and dye dyeing rate. Specific examples include (anhydrous) sodium sulfate, sodium chloride, ammonium acetate, ammonium sulfate, etc., and the content thereof in terms of weight percent is preferably in the range of 3 to 30% of the dyeing solution.

In addition, various conventionally known pH adjusters, penetrants,
Antifoaming agents, bath softeners, solubilizing agents, reduction inhibitors, leveling agents, slow dyeing agents, carriers, migration inhibitors, etc. can be added as necessary.

As a typical example, specifically, as a pH adjuster (
ice) ammonium acetate, sulfuric acid, anthonicum sulfate, and urea as a dissolving agent. In addition, it also has the effects of penetrating, level dyeing, and slow dyeing agents, including fatty acid salts, alkyl phosphate ester salts, alkylbenzenesulfone i*u, alkylnaphthalene sulfonates, dialkyl sulfosuccinates, alkyl phosphate ester salts, and naphthalene sulfones. Acid formalin condensate, polyoxyethylene alkyl (dLPfR ester salt, polyoxyethylene alkyl ether, polyoxyethylene alkyl phenyl ether, polyoxyethylene fatty acid ester, sorbitan fatty acid ester,
Particularly important are various anionic and nonionic surfactants such as polyoxyethylene sorbitan fatty acid ester, polyoxyethylene alkylamine, glycerin fatty acid ester, and oxyethylene oxybrobylene block polymer.

As mentioned above, the dyeing solution of the present invention does not necessarily have problems with level dyeing, color tone, problems in the dyeing process, and various fastnesses of dyed products when dyeing with a dyeing solution using conventional commercially available acid dyes. Our desire was to solve the unsatisfactory problems at the same time, 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 a blended nonwoven fabric (11) or a blended nonwoven fabric, or even to a shape other than a fiber, by a conventionally known dyeing method, such as dip dyeing, badging, or printing.

The temperature during dyeing, for example, the temperature of the dye bath and badging bath, etc., depends on the dyeing concentration, the polarity of the dye, the type of material to be dyed, and the temperature of the bath.
If the dyeing is insufficient, further dyeing treatment is performed, for example, by the steaming method, HT steaming method, thermofix method, or thermosol method, and then The dye is removed by a known cleaning process 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 specifically explained with reference to Examples and Comparative Examples. In addition, unless otherwise specified, parts in the text are based on In j11 standards.

Example 1 (Preparation of !A color liquid) 10 parts of anhydrous sodium sulfate (No.
, l) Pigment Compound Tripartite Urea
5 parts thiodiethylene glycol 5 parts anionic surfactant (dialkyl sulfosuccinate) 1 part water
80 part F
All the ingredients were stirred for 3 hours and the pH was adjusted to 3 with sulfuric acid to obtain a staining solution (a) of the present invention.

Example 2 (Preparation of staining solution) Anhydrous sodium carbonate 0.5 parts (NO,
2) Pigment compound Sin triethylene glycol monobutyl 5 parts Ether water 90
part, L: The gold component was stirred for 3 hours, and the pH was adjusted to 3 with acetic acid.
．． The staining solution (b) of the present invention was obtained.

Example 3 (Preparation of staining solution) Ammonium sulfate 5Ii5(N
o, 4) Pigment compound 2 parts Nonionic surfactant 1? I5 (Product name: Carazol LT, manufactured by Dai-Kogyo F) Water
93 parts All of the above components were stirred for 3 hours and adjusted to a pH of about 5 with pentaacetic acid to obtain a staining solution (c) of the present invention.

Comparative Example 1 (Preparation of staining solution) The dye compound of (No. 1) was mixed with C, 1, Ac1d 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 (staining solution made by s4) The dye compound of (No. 2) was mixed with C31,^cid ne
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. That f&60
The temperature was gradually raised to the boiling point over a period of minutes, and dyeing was carried out for 45 minutes in that state. The dyed material was soaped and thoroughly washed repeatedly.

Example 5 (Dyeing method) A sufficiently purified nylon cloth was buzzed with the dyeing liquid (b) 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) A silk cloth that had been thoroughly soaked and impregnated with water was immersed in the dyeing solution (c) shown in Example 3 at a bath ratio of 1:50, and heated to 40°C. It was warmed and left for 10 minutes. Thereafter, the temperature was gradually raised to 80° C. over a period of 30 minutes, and dyeing was continued for 45 minutes in that state. 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 a comparative staining solution (d).

Comparative Example 4 (Dyeing 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).

−Ko ni 2 history (− Dyeing, level dyeing, 1 piece, color tone -Retsu- Once in a while 'IJMJ! iA　OOOO mﾂ　oo　　　o　.

Pus cord chewing o OOO Fat crane grudge 0 Δ Δ Δ m Mosquito box A　Δ　　XXO The evaluation and evaluation criteria in the above table are shown below.

*1 Level dyeing property The dyeing was visually judged.

○・−1・There is no unevenness at all.

Δ---There is some unevenness.

*2 Indication fastness resistance: 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.

+i? The value is L$B according to the CIE LAB color system of the test piece.
Points on the coordinate system were determined using this conversion formula to b*, and the calculation was performed based on the color difference (ΔEab*) between the two points of the irradiation chamber and the sample after irradiation.

0-1-ΔEab*<5 △−−−−S≦ΔE ab*≦lO ×−−ΔEab*>t.

*3 Washing fastness synthetic detergent New Beads (product name: Kako) 0 not included,
The value of 51 was determined using ΔEab* in the same manner as the light fastness.

○−・−ΔEaM<5 Δ--5≦ΔE ab*≦10 X-----ΔEab*>10 Book 4 color tone The dyed matter was judged by IJ vision.

0-1 Bright magenta color.

△・−The color is slightly off from magenta.

Although the present invention has been described using the several dye compounds as representative examples, all of the dye compounds illustrated above other than those used in the examples exhibited 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, silk, nylon, polyacrylic fibers, polyurethane fibers, or woven fabrics containing these fibers. When dyeing non-a fabrics, warm-spun woven fabrics made of these fibers and other fibers, blended impure Ji, or blended non-woven fabrics, the dyeing is more uniform than when dyeing solutions using conventional commercially available acid dyes are used. It has excellent dyeability, and the dyed product has extremely good light fastness and washing fastness.

The color tones of dyed products are also vivid, making it suitable for color matching by mixing colors.

Patent applicant Canon Co., Ltd. agent Patent attorney -= II+ Katsuhiro:・', 2
・.

・-me】゛-r Hand 4 sale city IE’u,! , F (voluntary) 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) (However, Y_1 in the above formula is a hydrogen atom, a halogen atom,
It represents an alkyl group, an alkoxy group, a nitro group, an alkylsulfonylamino group, an arylsulfonylamino group, a triazinylamino group, an acylamino group, a -COOM group, or a -SO_3M group, and Q is an alkoxy group, an acylamino group, a hydroxyl group, a trianidine It represents a phenyl group or a naphthyl group which may be substituted with a dylamino group, n represents 1, 2 or 3, M represents an alkali metal, ammonium or amines, and W represents Cu, Co or Ni. However, in Q, the azo group and the -O- group are located at the ortho position. ) (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) (4) The object to be dyed is wool, silk, nylon, polyacrylic fiber, polyurethane fiber, woven fabric or non-woven fabric containing these fibers, or warm-spun woven fabric or blended non-woven fabric consisting of these fibers and other fibers. A dyeing method according to claim (3).