JPS607755B2 - Dyeing method for polyester synthetic fibers - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention provides a method for dyeing polyester synthetic fibers or blended, interwoven, and interwoven fabrics of polyester synthetic fibers and other fibers at high temperatures using disperse dyes or dispersed Azozic dyes. This invention relates to a dyeing method for obtaining a dyed product.

In recent years, with the development of so-called rapid dyeing (short-time dyeing) methods, there has been a demand for beam coloring auxiliaries with low foaming properties and an initial slow beam type.

On the other hand, ``With the tightening of regulations on factory wastewater, the treatment of these dyeing aids has become a major social issue. Conventionally, ester-type or ether-type nonionic activators have been used as dyeing aids for rapid dyeing. However, these activators have problems such as dispersion destruction and a decrease in the final dyeing amount due to cloud point phenomenon at high temperatures, and furthermore, they cannot be removed by factory wastewater treatment methods such as coagulation treatment methods. There are some drawbacks that cannot be avoided.

In addition, to compensate for these drawbacks, anionic activators have been added to the formulation, but as this generally increases foaming properties, antifoaming agents are often used in combination, resulting in the formation of scum, staining, etc. Problems have also arisen. The present inventors have arrived at the present invention as a result of intensive studies to solve such problems. Alkylphenol having 12 alkyl groups (or formaldehyde condensate thereof)
, a residue of an arylphenol (or formaldehyde condensate thereof) having 2 to 6 benzene moieties, or an alkylarylphenol having an alkyl group having 1 to 12 carbon atoms and 2 to 6 benzene rings ( or formaldehyde condensate thereof), R2 has 2 carbon atoms
-6 alkyl (or alkenyl) dicarboxylic acid residue or C2-6 alkyl (or alkenyl) benzene dicarboxylic acid residue, m or n is 0-500
The integer and M represent potassium, sodium, calcium, magnesium, barium, ammonium, N-alkanolammonium having 6 or less carbon atoms, or N-alkylammonium having 6 or less carbon atoms.

] or (and) general formula [where R3 is a residue of a formaldehyde condensate of an alkylphenol having an alkyl group having 1 to 12 carbon atoms, 2
- Residue of formaldehyde condensate of arylphenol having 6 benzene rings or residue of formaldehyde condensation of alkylarylphenol having alkyl group having 1 to 12 carbon atoms and 2 to 6 benzene rings, R
4 is a higher fatty acid residue having 8 to 22 carbon atoms, and R5 is a residue having 2 carbon atoms.
Residue of alkyl (or alkenyl) dicarboxylic acid having ~6 or residue of alkyl (or alkenyl) benzene dicarboxylic acid having 2 to 6 carbon atoms, p, q, s or t is 0
The integer of ~500 and M represent potassium, sodium, calcium, magnesium, /dium, ammonium, N-alkanolammonium having 6 or less carbon atoms, or N-alkylammonium having 6 or less carbon atoms.

] This is a dyeing method characterized by adding one or more compounds represented by the following to the dyeing process.

Examples of R in the compound represented by the general formula [A] include the following residues of the compound. {1) Octyl alcohol, lauryl alcohol, myristyl alcohol, palmityl alcohol,
Oleyl alcohol, stearyl alcohol/shi {2}
Cresol, pt-butylphenol, octylphenol, nonylphenol, dinonylphenol, dodecylphenol, cyclohexylphenol, or
These pendylated or styrenated products Chlorophenol, cumylphenol, phenylphenol, naphthol or their pendylated or styrenated products {41 Bisphenol, resorcin or their pendylated or styrenated products [5} [2}, [3] ' or {4} formaldehyde condensate In addition, R3 of the compound represented by the general formula [B] may be a residue of a compound exemplified by '4} or {5} in the above example, and R4 For example, residues such as caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, terracotta fatty acid, and tall oil fatty acid can be exemplified.

Further examples of R2 or R5 of the compound represented by the general formula [A] or [B] include maleic acid, fumaric acid,
These are residues of succinic acid, adipic acid, phthalic acid, or terephthalic acid, but in actual synthesis it is also possible to use acid anhydrides such as maleic anhydride, succinic anhydride, or phthalic anhydride.

The compounds used in the present invention can be easily obtained by known methods.

That is, the compound represented by general formula [A] is an ether type/ion obtained by adding ethylene oxide or (and) propylene oxide to the compound listed as an example of R, and the dibasic acid listed as an example of R2 or R5. (or their acid anhydrides) and then neutralized with an alkali. In this case, the amount of dibasic acid used is equal to or less than the amount of hydroxyl groups possessed by the ether type nonion. or,
In the compound represented by the general formula [B], R4 is a part of the hydroxyl group of an ether type nonion obtained by adding ethylene oxide or (and) propylene oxide to the compound exemplified for R3. esterification with the higher fatty acid, then the remaining hydroxyl group and R2 or R5
It can be easily obtained by reacting with the dibasic acids (or their acid anhydrides) listed as examples and neutralizing with an alkali.

In this case, the amount of higher fatty acid used is 1/2 equivalent or less of the hydroxyl group possessed by the ether type nonion, and the amount of dibasic acid (or acid anhydride thereof) used is equivalent to the remaining hydroxyl group. It is. The amount of ethylene oxide or propylene oxide to be added is preferably 50 to 30% by weight based on the weight of the hydrophobic group raw material, but especially when propylene oxide is used, it is preferable that propylene oxide and ethylene oxide in an amount greater than the number of moles of propylene oxide added,
Moreover, it is preferable that the total addition of propylene oxide and ethylene oxide is 50 to 30% by weight based on the weight of the hydrophobic group raw material.

The beam coloring auxiliary agent of the present invention is a known dyeing agent, such as an alkyl (alkenyl) of polyoxyethylene alkyl (alkenyl) ether
alkenyl) ester, alkyl (alkenyl) ester of polyoxyethylene arylphenol ether,
Or, compared with mixtures of these and polyoxyethylene alkyl (alkenyl) ether sulfate, polyoxyethylene aryl phenol ether sulfate, etc., it is particularly excellent in the following properties. 1 Dye transfer effect,
Excellent permeability.

2. There is almost no decrease in the final dyeing amount.

3 Extremely low foaming.

(In particular, the higher the temperature and the more acidic the foam, the lower the foaming property.
) 4 Excellent wastewater treatment properties (coagulation treatment properties).

Although the beam coloring aid of the present invention can be used alone,
Among the compounds represented by the general formula [A], particularly preferred are:
Among the compounds listed as examples of R, compounds using (1' or nonylphenol, dinonylphenol, or octylphenol) and compounds listed as examples of R,
It is used in combination with a compound represented by the general formula [A] using 31 to [51] or a compound represented by the general formula [B], in which case the dye penetrating property of the former compound and that of the latter two compounds are Due to the mutual effect with the moderate dye affinity that it has, it exhibits a particularly excellent leveling effect. In this case, the blending ratio of the former and the latter is 9:1 to 1:9, particularly preferably 7:3 to 3:7. The beam coloring auxiliary agent of the present invention usually exhibits its effect by adding 0.1 to 18' in the dyeing agent. Furthermore, the compound of the present invention can be used in combination with a dyeing aid, so-called covering agent, which is used for the purpose of preventing streaks, etc., to improve the covering effect. It is also possible to use it as a soaping agent for dyed products by using it in combination with alkali and alkali.Alternatively, among the compounds represented by the general formula [A], R is particularly an alcohol having 10 to 14 carbon atoms, nonylphenol or dinonylphenol. In the case of enol etc., it can also be used as a scouring agent.

Examples of the present invention are shown below.

Example 1 A solution containing 0.3 liters of crab dyeing aid and 0.12 liters of acetic acid was placed in a column with an inner diameter of 5 arcs, and 600 liters of nitrogen gas was introduced from the bottom.
The foaming properties were measured while increasing the temperature of the column.

Table 1 Test dyeing/auxiliary agent The sample beam color aids are shown in Table 1, and the test results are shown in Table 2.

Table 2 Test Results Example 0 Polyester processed yarn fabric (manufactured by Teijin) was dyed under the following conditions.

Amount of dye used: 1% o. w. f. pH: 4.5 (adjusted with 80% acetic acid) Yuhi: 1:30 Dyeing temperature and time: 13000 x 3 minutes The test dyes are as follows.

1 Dianix Orange B-SE 2 Dianix Red KB-SE 3 Dianix Full KB-FS Next, the fabric to be dyed is placed in a beam color auxiliary solution along with the same amount of white fabric. A relocation test was conducted under the following conditions.

Amount of dyeing aid used: 1 mochi/L pH: 4.5 (adjusted with 80% acetic acid) Dyeing temperature and time: 1300oo x 30 minutes The dyeing aids shown in Table 1 were used for dyeing. The machine used was Karamaster HD-12 (manufactured by Tsujii Someki Kogyo ■).

The test results are shown in Table 3.

◎ (Good beam transferability) ~ △ (Slightly good) ~ x (Poor) Example m Samaron Flu HBLO. 58/L, beam color aid 1
Approximately 1 skin of one end of a commercially available processed polyester yarn fabric cut into 1 skin was immersed in a solution 100% adjusted to have a concentration of bait/L and acetic acid of 0.4 cc/L. The time for the solution to rise to 200 oo and the degree of rise after 5 minutes.
It was measured with

The test results are shown in Table 4. Table 4 Test Results Example W A commercially available polyester processed yarn fabric (Tropical) was dyed under the following conditions.

Amount of dye used: 1% o. w. f. Amount of auxiliary agent used: 18/L PH: 4.5 (adjusted with 80% acetic acid) Yield ratio: 1:30 Dyeing temperature and time: 130qo x 3 Dyeing machine: Karamaster HD-12 Next, dye the fabric 8000x containing poly(30)oxyethylene hexadecylamine 1 bait/L, sodium hydroxide 1 gr'L and hydrosulfite 1 gr/L
Reduction cleaning was performed for 10 minutes, and after further washing with water and drying, the reflectance was measured. From this, the K/S value was calculated and the dyeing rate was compared.

The dyes used are as follows.

1 Sumikalon Yellow Brown S-2RL2 Huolon Rubin S-20FL3 Dianix Blue RN1E The test results are shown in Table 5.

Table 5 Test Results Sweat) The values in the table are the K/S value of the dyed fabric without the addition of auxiliary agents.
Expressed as 00.

Example V Tetoron taffeta was used for staining under the following conditions.

Dye and its usage amount: Calon Polyester Blue TSF I%o. w. f. Amount of auxiliary agent used: IQ/L pH: 4.5 (adjusted with 80% acetic acid) Yield ratio: 1:30 Dyeing temperature and time: 130oo x 30 minutes Dyeing machine used: Colorpet 12 (manufactured by Nippon Senzo Kikai) The dyed material was subjected to reduction cleaning in the same manner as in Example W, washed with water, and dried. The level dyeing property of the dyed material was visually judged.
1.No. 2.No. 3 and NO. When dyeing with No. 4, no beam spots were observed, but when no auxiliary agent was added, considerable staining spots were observed. 1 and no. In case 2, some beam spots were also observed.

In the dyeing aid solution with a concentration of 100 in Example, 15% of polyaluminum chloride was added.
The skin was added, and the pH was adjusted to 7 to 8 with calcium hydroxide, followed by flocculation treatment.

The TOC of the beam color auxiliary agent solution was measured before and after the aggregation treatment, and the aggregation treatment rate was calculated using the following formula. Agglomeration treatment rate (%) = TOC before treatment - TOCXI after treatment.

〇 The TOC test results before treatment are shown in Table 6.

Table 6

Claims (1)

[Claims] 1. When dyeing polyester synthetic fibers or blended, interwoven, or interwoven fabrics of polyester synthetic fibers and other fibers using disperse dyes or dispersed azoic dyes at high temperatures,
General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [However, R_1 is a residue of a higher alcohol having 8 to 22 carbon atoms, or an alkylphenol having an alkyl group having 1 to 12 carbon atoms (or a formaldehyde condensate thereof). basis,
Residues of arylphenols having 2 to 6 benzene rings (or formaldehyde condensates thereof) or alkylarylphenols having an alkyl group having 1 to 12 carbon atoms and 2 to 6 benzene rings (or their formaldehyde condensates) R_2 is a residue of an alkyl (or alkenyl) dicarboxylic acid having 2 to 6 carbon atoms or a residue of an alkyl (or alkenyl) benzene dicarboxylic acid having 2 to 6 carbon atoms, m or n is 0 to The integer 500 and M represent potassium, sodium, calcium, magnesium, barium, ammonium, N-alkanolammonium having 6 or less carbon atoms, or N-alkylammonium having 6 or less carbon atoms. ] Or (and) general formula ▲ Numerical formula, chemical formula, table, etc. ▼ [However, R_3 is a residue of a formaldehyde condensate of an alkylphenol having an alkyl group having 1 to 12 carbon atoms,
The residue of a formaldehyde condensate of an arylphenol having 2 to 6 benzene rings, or the residue of a formaldehyde condensation of an alkylarylphenol having an alkyl group having 1 to 12 carbon atoms and 2 to 6 benzene rings,
R_4 is a higher fatty acid residue having 8 to 22 carbon atoms, R_5 is a residue of alkyl (or alkenyl) dicarboxylic acid having 2 to 6 carbon atoms or a residue of alkyl (or alkenyl) benzene dicarboxylic acid having 2 to 6 carbon atoms, p, q, s or t is an integer of 0 to 500 and M is potassium, sodium,
Calcium, magnesium, barium, ammonium,
Indicates N-alkanol ammonium having 6 or less carbon atoms or N-alkylammonium having 6 or less carbon atoms. A dyeing method characterized by adding one or more compounds represented by ] to a dye bath.