JPH07100911B2 - Dyeing method for polyester fiber - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION <Industrial field of application> The present invention relates to a dyeing method for a polyester fiber, which has particularly excellent fastness to washing after post-processing.

<Prior Art> In recent years, as consumer needs for textile products have become higher-grade and differentiated products, polyester fibers have a tendency to be made into natural fibers. Various techniques have come to be applied such as water absorption and perspiration, anti- (flame-retardant) flame prevention, anti-melting, anti-fouling, hygiene, deep coloration, texture improvement and moisture-permeable waterproofing. These mixed spinning mixed weaving technology and post-processing technology enhance fashionability and comfort, and make it high-class,
On the other hand, there is a problem that the wet fastness of the fiber is lowered more than ever before, though it is differentiating.

That is, it is considered that a dyed product of polyester fiber with a disperse dye can obtain high wet fastness when subjected to sufficient reduction washing during the dyeing process. However, even in the case of such a dyed product, when the high temperature heat setting treatment is performed to perform the post-processing for imparting various functionalities as described above, the disperse dye dyed in the fiber is Thermomigrates on the surface and wet fastness decreases. Therefore, when pursuing functionality, a product having high wet fastness cannot be obtained, and when high wet fastness is required, it is difficult to obtain high functionality.

On the other hand, with respect to wet fastness, consumers' needs have become more sophisticated and diversified, and in particular, regarding wash fastness, there is a movement to revise or establish a fastness test standard in order to meet such needs. For example, in the UK Marks & Spencer (M & S) company ISO (Inter
We have reviewed our national standard) washing fastness and set our own in-house standard. Since this M & S standard is severe, even for deep-colored dyes, of grade 4 or higher, high wet fastness dispersants developed by various companies (for example, JP-A-56-50959,
In Japanese Patent Publication No. 45-7712 and Japanese Patent Publication No. 61-200170), mixed fast-spun woven products and various post-processed products did not have sufficient fastness, and none of the red disperse dyes could pass.

<Problems to be Solved by the Invention> The present invention provides a dark-colored dyeing having high wash fastness even when subjected to various post-treatments and heat-setting for the purpose of imparting functionality to polyester fibers. The purpose is to provide a method of

<Means for Solving Problems> The inventors of the present invention have made extensive studies to solve the above problems, and have completed the present invention by reviewing that the object can be achieved.

That is, the invention has the general formula (I) [In the formula, X, Y and Z each independently represent a hydrogen atom, a chlorine atom or a NO ₂ group, A and B each independently represent a hydrogen atom, a halogen atom, a lower alkyl group or a lower alkoxy group, and R ₁ And R ₂ are each independently OCOR ₃ , O
COOR ₃ (wherein R ₃ represents a lower alkyl group) or an optionally substituted phenyl or phenoxy group. ] A monoazo dye represented by the formula (II) [In the formula, FI is an index indicating fastness, particularly wet fastness,
[D] _HL is a numerical value representing the inorganicity / _organicity of the dye,
[M] _D represents the molecular weight of the dye. ] The process of dyeing a polyester fiber using a monoazo dye having an FI value of 100 or less
A method for dyeing a polyester fiber, which comprises a step of performing a heat setting treatment at 150 ° C. or higher for 20 seconds or longer.

According to the method of the present invention, the effect is remarkable when dyeing at a density of JIS Standard Dyeing Density Table No. 1 or higher, particularly when dyeing at a density twice the density (extreme dark color) or higher.

Represents the inorganic / organic nature of the dye in formula (II) [D]
_The numerical value indicated by _HL indicates the balance between hydrophilicity and hydrophobicity of the dye, Fujita, systematic organic qualitative analysis, pure edition,
It can be calculated by the method described on pages 61 to 84 (1953). The FI value obtained by dividing this value by the molecular weight [M] _D of the dye and multiplying it by a specific constant in formula (II) shows a good correlation with fastness, especially wet fastness including wash fastness. is there.

A monoazo dye represented by the general formula (I) and having the formula (I
Examples of the monoazo dye represented by I) having a FI value of 100 or less include the monoazo dyes represented by the following formulas (a) to (p).

These dyes are liquid products obtained by adding a dispersant such as a formalin condensate of naphthalene sulfonic acid or a lignin sulfonic acid to the wet cake, and then atomizing and dispersing the mixture in a sand mill or spray drying. The obtained powder product is used for dyeing polyester fibers.

These dyes have various hues as well as a single color,
It can also be used by blending dyes satisfying the respective conditions, and the blending method may be either a method of blending as a powder product or blending in a liquid state and then spray drying.

The polyester fiber used in the present invention may be polyester fiber or a mixed spun woven product thereof.

In the practice of the present invention, the polyester fiber is immersed in a dyeing bath in which the above-mentioned monoazo dye is dispersed in an aqueous medium, and dyeing is carried out under pressure at 105 ° C or higher, preferably 110 ° C to 140 ° C.

It is also possible to dye in the presence of a carrier such as o-phenylphenol or methylnaphthalene at a relatively high temperature such as a boiling state of water.

Furthermore, a dyeing method in which the dye dispersion is padded on the cloth and then steaming or dry heat treatment is performed at 100 ° C. or more is also possible.

On the other hand, in the case of printing, the dye dispersion is kneaded together with an appropriate sizing agent, printed on a cloth, and then steamed or dry heat treated.

The dyed product thus obtained is subjected to reduction washing treatment by a known method, or it is omitted and various finishing agents are added as required, and then heat setting treatment is performed. The heat setting treatment is carried out at 150 ° C. or higher and for 20 seconds or longer, but a sufficient effect cannot be obtained at this temperature or lower time, and dry heat treatment at about 170 ° C. for about 30 seconds is preferable.

According to the method of the present invention, even when various post-treatments are applied to polyester fibers, there is no wrinkle, excellent dimensional stability, and high washing fastness without impairing the effect of the post-treatments applied. It is possible to obtain a deep-colored dyeing product that can pass the M & S standard.

Hereinafter, the present invention will be described in more detail with reference to examples. In the text, parts represent parts by weight, and% represents% by weight.

Example 1 0.8 parts of the monoazo dye represented by the formula (a) was commercialized with 2.2 parts of a dispersant of a formalin condensate of naphthalenesulfonic acid, 3.0 parts of disperse dye, 0.6 part of acetic acid, 2.4 parts of sodium acetate, and Sumipon TF (Sumitomo TF). Chemical Industry Co., Ltd. dyeing assistant) 1.5
100 parts of Tetron Tropical (polyester-processed woven fabric manufactured by Teijin Ltd.) was dyed at 130 ° C. for 60 minutes in 1500 parts of a dye bath containing 100 parts. After dyeing, wash in a reducing bath consisting of 40 ° B'e NaOH 2 ml / l, Score Roll 400 (Kao Corp. detergent) 1 ml / l and Na-hydrosulfite 2 g / l, wash with water and dry. To obtain a red dyed product.

Then, the following post-processing was applied to finish. That is, the above dyed product was padded (squeezing ratio 100%) in a resin bath consisting of 20 parts of Permalose ™ (ICI's antistatic and antifouling agent) and 980 parts of water, and dried at 80 ° C. Finished by heat setting at 170 ° C for 30 seconds.

The results of checking the fastness of the finished dyed product according to the following method are shown in Table 1 below, and all show good fastness, and in particular, the wash fastness-2 shows a grade 4. It was

(Fastness test method) (1) Light fastness In accordance with JIS L-0842 method, the dyed fabric was exposed with a blue scale under a carbon arc lamp for 80 hours to compare the discoloration of the dyed fabric with the discoloration of the blue scale. The robustness was judged.

(2) Fastness to sublimation According to JIS L-0850 method, polyester cloth is used as an attached cloth, and the surface temperature is 180 ° C under an electric iron.
Second treatment was performed, and the fastness was judged by comparing the degree of discoloration of the dyed fabric and the degree of contamination of the attached fabric with a gray scale.

(3) Water fastness Dyeing cloth was tested in accordance with JIS L-0846A using nylon and silk cloth as the attached cloth, and the discoloration of the dyed cloth and the degree of contamination of the attached cloth were compared with grayscale. Then, the fastness was judged.

(4) Washing fastness-1 Multi-woven mixed woven cloth (No.1) is attached to the dyed cloth, and AATCC method washing II
-A test was conducted in accordance with No. A, and the degree of fastness was judged by comparing the discoloration of the dyed fabric and the degree of contamination of the acetate and nylon parts in the multi-woven mixed fabric with a gray scale.

(5) Washing fastness-2 Other than using a multi-woven mixed woven fabric (No.10A) attached to the dyed fabric and using the following formulation as the washing liquid
A test was carried out in accordance with ISO method laundry No. C-03, and the fastness was judged by comparing the discoloration and discoloration of the dyed cloth and the degree of contamination of the acetate and nylon parts in the multi-woven cloth with gray scale.

Washing liquid treatment method ECE detergent 4g / l Sodium perborate 1g / l For comparison, the dye (q) (FI = 126) was used instead of the monoazo dye of the above formula (a). When the dyeing process is performed, a dyed product having the same density and hue is obtained, and the general fastness [fastness test item (1) to
(4), the same applies hereinafter) was not a problem, but the stain of washing fastness -2 was grade 3, which was beyond the standard.

(See Table 1) Example 2 Disperse dye obtained by commercializing 0.7 part of the monoazo dye represented by the formula (b) with 2.3 parts of a sodium lignin sulfonate dispersant.
100 parts of tetro jersey (polyester processed fabric manufactured by Teijin Ltd.) was dyed at 130 ° C. for 60 minutes in 1500 parts of a dyeing bath containing 3.0 parts and the same dyeing assistant as in Example 1. After the completion of dyeing, the same washing treatment as in Example 1 was carried out, and then the following post-processing, that is, Elastron F-29 (Daiichi Kogyo Co., Ltd. water-soluble urethane resin, texture improver), 30 parts , Catalyst 32 (Daiichi Kogyo's catalyst, special nonionic activator)
The above dyed product was padded (squeezing ratio 90%) in a resin bath consisting of 3 parts, 0.06 part of heavy sow and 967 parts of water, dried at 120 ° C., and finally heat set at 150 ° C. for 1 minute,
A red dyed product rich in resilience was obtained.

The fastness of the obtained dyed product was tested in the same manner as in Example 1. The results are shown in Table 1, and all had good fastness.

Comparative Example 2 Instead of the monoazo dye of the above formula (b), the dye (r) (FI
= 120) was used and dyeing was carried out in the same manner as in Example 2 to obtain a dyed product having a similar density and hue, but the stain resistance of washing fastness-2 was 2-3 and poor. , I could not pass the standard.

Example 3 0.7 parts of the monoazo dye represented by the above formula (k) was commercialized with 2.3 parts of sodium naphthalenesulfonate-based dispersant, 3.0 parts of a disperse dye, and 12% of Mayprogum NP (a guar-based paste manufactured by Mayhole Chemical AG) paste. Auto-screening a color paste consisting of 60.0 parts, Sunfloren SN (Nikaka Chemical Co., Ltd.) 3.0 parts and water 34.0 parts on Tetoron Georgette (Teijin Co., Ltd. polyester strong twist thin fabric) Printing was performed using a printing tester (manufactured by Tsujii Dyeing Machine Co., Ltd.) and dried at 120 ° C. Then use a high temperature steamer (manufactured by Tsujii Dyeing Machine Co., Ltd.) at 175 ° C.
After the fixing treatment for 8 minutes, washing with water, washing with hot water and the same reduction washing treatment as in Example 1 were performed to obtain a red printed material.

The resulting printed material is subjected to the following deep color and texture improving processing,
In other words, 300 parts of Sumitex resin EM-11 (fluorine-based resin processing agent manufactured by Sumitomo Chemical Co., Ltd.), Sumistat F
-1 (Sumitomo Chemical Co., Ltd. antistatic processing agent) 50 parts, Sumitex Silicon Softener 10 (Sumitomo Chemical Co., Ltd. softening processing agent) 200 parts and water 450 parts (80% squeezing ratio), dried at 80 ° C, and finally heat-set at 160 ° C for 30 seconds.

The obtained processed products were dark-colored prints having a silky texture, and the fastness test results as in Example 1 were all excellent. (See Table 1) Comparative Example 3 Instead of the monoazo dye of the above formula (k), the dye (s) (FI
= 104) and then processed in the same manner as in Example 3 to obtain a print having a similar density and hue, and although the general fastness was not so different, the fastness to washing-2 The pollution was so bad that it was in the 2nd to 3rd class and could not pass the standard. (See Table 1) Example 4 2.0 parts of a disperse dye prepared by commercializing 0.4 part of the compound represented by the formula (e) with 1.6 parts of a formalin condensate dispersant of sodium naphthalenesulfonate, and the same dyeing as in Example 1 100 parts of polyester / cotton (50/50) knit (manufactured by Teijin Ltd., unmercured product) was dyed at 130 ° C. for 60 minutes in 1500 parts of a dye bath containing an auxiliary agent. After the completion of dyeing, the same reduction washing treatment as in Example 1 was performed, followed by drying at 60 ° C and final setting at 170 ° C for 30 seconds to obtain a red dyed product.

The results of testing the fastness of the obtained dyed product in the same manner as in Example 1 are shown in Table 1, and all the items were excellent.

Comparative Example 4 Instead of the disperse dye of the above formula (e), the dye (t) (FI = 11
Dyeing was performed in the same manner as in Example 4 except that 7) was used, and a dyed product having a similar concentration and hue was obtained, but the wash fastness-2 was too much to pass the specifications. there were.

Structural formula of the dye used in Comparative Example 1 Structural formula of the dye used in Comparative Example 2 Structural formula of the dye used in Comparative Example 3 Structural formula of the dye used in Comparative Example 4

 ─────────────────────────────────────────────────── ─── Continuation of front page (72) Inventor Kiyoho Hashimoto 3-98 Kasugadechu, Konohana-ku, Osaka-shi, Sumitomo Chemical Co., Ltd. (56) Reference JP-A-57-121676 (JP, A) JP-A-58-160355 (JP, A)

Claims (1)

[Claims] 1. A general formula (I) [In the formula, X, Y and Z each independently represent a hydrogen atom, a chlorine atom or a NO ₂ group, A and B each independently represent a hydrogen atom, a halogen atom, a lower alkyl group or a lower alkoxy group, and R ₁ And R ₂ are independently OCOR
₃ , OCOOR ₃ (wherein R ₃ represents a lower alkyl group),
Alternatively, it represents an optionally substituted phenyl or phenoxy group. ] A monoazo dye represented by the formula (II) [In the formula, FI is an index indicating fastness, particularly wet fastness,
[D] _HL is a numerical value representing the inorganicity / _organicity of the dye,
[M] _D represents the molecular weight of the dye. ] The FI value represented by is characterized by including a step of dyeing a polyester fiber with a monoazo dye having a FI value of 100 or less, and a step of heat-setting the dyed product at 150 ° C. or more for 20 seconds or more. A method for dyeing and processing polyester fibers.