JPH0718585A - Method for dyeing polyester-based fiber - Google Patents

Abstract

PURPOSE:To obtain a dyed material excellent in fastness to light by adding a dispersion of a specific ultraviolet absorbing agent to a dyeing bath in a high-temperature state and continuing dyeing when dyeing a polyester-based fiber. CONSTITUTION:In dyeing a polyester-based fiber, one kind of ultraviolet absorbing agent selected from ultraviolet absorbing agents of formula I and formula II (X1 to X6 are each H, halogen, OH, a 1-8C alkyl, aryl, benzyl, alkoxy, aryloxy, benzyloxy, tetrahydrophthalimidemethyl) and formula III (X7 and X8 are same as the X1 to X6 in the above description from H to benzyloxy group or amino, aminoalkyl or aminoaryl; X9 and X10 are same as X1 to X6 in the description from H to aryloxy group) and formula IV (R is a 1-8C alkylene; X11 to X12 are H or OH; X12 and X14 are same as X7 and X8 in the description from H to aryloxy group) is added to a dyeing bath heated to 100-140 deg.C and then kept in the same temperature and the polyester-based fiber is treated with the ultraviolet absorbing agent at 120-140 deg.C for 5-30min to provide the objective dyed polyester fibers excellent in fastness to light.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a dyeing method for polyester fibers. The present invention, in particular, when dyeing a fiber material composed of a polyester fiber or a mixed fiber of a polyester fiber and another fiber with a dye such as a disperse dye or a cationic dye, the sun fastness of the obtained product is improved. It relates to a method that can be significantly improved.

[0002]

2. Description of the Related Art Textile products made of polyester fibers are now widely used as various industrial materials and are becoming increasingly important as automobile interior materials. In particular, in recent years, automobile interior materials have been made into fabrics more and more due to the trend toward higher quality and higher performance, and further, higher degree of fastness to sunlight has been required for these cloth products and the like. Is coming. That is, regarding the fastness to sunlight,
200-40 at 83 ° C in high temperature fade odometer
It is required to have a high performance of passing grade 3 under the condition of irradiation for 0 hours.

In order to impart sunlight resistance to a polyester fiber dyeing product, a dye having excellent fastness to sunlight is selected, and an ultraviolet absorber generally called a light fastness improving agent is used in the first stage of dyeing, that is, a dipping bath. When preparing, a method is generally used in which a dye, a pH adjuster, a dispersion leveling agent, and the like are added, and the dye and the dye are adsorbed to the textile product in a single step.

[0004]

The conventional method in which an ultraviolet absorber is added to the dyeing bath in the first stage of the dyeing process so that the dye is adsorbed in a single step has achieved some effects, but a higher degree of resistance to sunlight. In the present situation, the effect of improving the fastness to sunlight is still insufficient when high performance is required or when a wider range of dyes must be used.

Accordingly, the present invention is intended to provide a method capable of significantly improving the fastness to sunlight of a product when dyeing a polyester fiber.

[0006]

The inventors of the present invention have arrived at the treatment method of the present invention as a result of intensive studies to solve the above problems. That is, when dyeing a fiber material composed of polyester fibers or fibers mixed with polyester fibers with other fibers with a dye such as a disperse dye or a cationic dye, first the dye is adsorbed, and then the light resistance improver is adsorbed. By carrying out the step treatment, it was found that the fastness to sunlight of the obtained product was significantly improved as compared with the general method of exhausting the dye and the light resistance improver in one step, and the present invention was completed. It is a thing.

Therefore, according to the present invention, when dyeing a fiber material composed of a polyester fiber or a mixed fiber of a polyester fiber and another fiber, the fiber material is put into a dye bath and the dye bath is heated at 100 to 140 ° C. After the temperature was raised, at least one type of aqueous dispersion selected from the ultraviolet absorbers represented by the following general formulas (I) to (IV) was added while maintaining this temperature, and at 120 to 140 ° C. After treating for 5 to 30 minutes or raising the temperature of the dyebath to 100 to 140 ° C., the temperature is once lowered, and then the following general formulas (I) to (I
V) at least one selected from the ultraviolet absorbers represented by
Add an aqueous dispersion of seeds and raise the temperature again to 120-140 ° C.
The method for dyeing a polyester fiber is characterized by treating the polyester fiber for 5 to 30 minutes.

[0008]

[Chemical 5]

[0009]

[Chemical 6]

In the above formula, X ₁ , X ₂ , X ₃ , X ₄ , X ₅ and X ₆ are each independently hydrogen, halogen, a hydroxyl group, an alkyl group having 1 to 8 carbon atoms, an aryl group or a benzyl group. , An alkoxy group, an aryloxy group, a benzyloxy group or a tetrahydrophthalimidomethyl group.

[0011]

[Chemical 7]

In the above formula, X ₇ and X ₈ are each independently hydrogen, halogen, hydroxyl group, alkyl group having 1 to 8 carbon atoms, aryl group, benzyl group, alkoxy group, aryloxy group, benzyloxy group, Represents an amino group, an aminoalkyl group or an aminoaryl group, X ₉ and X
_10's each independently represent hydrogen, halogen, a hydroxyl group, an alkyl group having 1 to 8 carbon atoms, an aryl group, a benzyl group, an alkoxy group or an aryloxy group.

[0013]

[Chemical 8]

In the above formula, R represents an alkylene group having 1 to 8 carbon atoms, X ₁₁ and X ₁₃ each independently represent hydrogen or a hydroxyl group, and X ₁₂ and X ₁₄ each independently.
Hydrogen, halogen, hydroxyl group, alkyl group having 1 to 8 carbon atoms,
It represents an aryl group, a benzyl group, an alkoxy group or an aryloxy group. The method of dropping the temperature and then adding the aqueous dispersion of the ultraviolet absorber is effective when using a dyeing machine in which it is difficult to add the treatment liquid under high temperature and high pressure.

Textile materials useful in the present invention include woven fabrics, knitted fabrics and non-woven fabrics made of polyester synthetic fibers or mixed fibers of polyester fibers and other fibers such as cotton, rayon, wool, nylon and acetate. Etc. The dyeing process can be performed under substantially the same conditions as the conventionally known process. That is,
A textile dyeing machine, with or without scouring of textile materials,
The processing is performed using a dyeing machine such as a beam dyeing machine or a cheese dyeing machine.

The ultraviolet absorber which can be used in the present invention is a benzotriazole type compound represented by the general formula (I),
A benzophenone-type compound of the general formula (II), a general formula (I
II) triazine-type compounds and general formula (IV) benzophenone-type dimer compounds. Specific examples of the benzotriazole-based ultraviolet absorber represented by the general formula (I) include 2- (2′-hydroxy-5′-methylphenyl) in which X ₁ and X ₂ are hydrogen and X ₃ is a methyl group. )
-Benzotriazole, X ₁ and X ₂ are hydrogen,
X ₃ is a t- butyl group 2- (2'-hydroxy -
5'-t-butylphenyl) -benzotriazole, X
2- (2'-hydroxy-3 ', 5'-t-butylphenyl) -benzotriazole wherein ₁ is hydrogen and X ₂ and X ₃ are each t-butyl groups, X ₁ is chlorine and X ₂ and X ₃ are each a t-butyl group 2-
(2'-hydroxy-3 ', 5'-t-butylphenyl) -5-chlorobenzotriazole, X ₁ is chlorine, X ₂ is a t-butyl group, and X ₃ is a methyl group 2- (2′-hydroxy-3′-t-butyl-5′-methylphenyl) -5-chlorobenzotriazole, X ₁
Is hydrogen and X ₂ and X ₃ are each a t-amyl group, 2- (2′-hydroxy-3 ′, 5′-t-amylphenyl) -benzotriazole, X ₁ and X ₂ are hydrogen. , X ₃ is a t-octyl group, 2- (2′-
Hydroxy-5′-t-octylphenyl) -benzotriazole, X ₁ is hydrogen, and X ₂ is 3 ″, 4 ″,
5 ″, 6 ″ -tetrahydrophthalimidomethyl,
2- {2'-hydroxy-3'- in which X ₃ is a methyl group
(3 ", 4", 5 ", 6" -tetrahydrophthalimidomethyl) -5'-methylphenyl} -benzotriazole and the like.

Benzophenone represented by the general formula (II)
Specific examples of the ultraviolet absorbers include X_FourAnd X_FiveBut water
Elementary and X₆2,4-dihydroxy ester in which is a hydroxyl group
Nzophenone, X_FourAnd X_FiveIs hydrogen and X₆The
2-hydroxy-4-methoxybenzophyl which is a toxy group
Kenon, X_FourAnd X_FiveIs hydrogen and X₆Is n-oct
2-Hydroxy-4-n-octoxybe which is a toxy group
Nzophenone, X_FourAnd X_FiveIs hydrogen and X₆Is
2-hydroxy-4-benzoi which is a benzoyloxy group
Luoxybenzophenone, X_FourIs a hydroxyl group, X_FiveBut
Hydrogen and X ₆2,2'-hydro in which is a methoxy group
Xy-4-methoxybenzophenone, X _Four, X_Fiveand
X₆2,2'-hydroxy-4,4'- in which is a hydroxyl group
Methoxybenzophenone, X_FourAnd X_FiveIs a hydroxyl group
X₆Is a methoxy group, 2,2'-hydroxy-
4,4'-dimethoxybenzophenone and the like can be mentioned.
It

Triazine type compound represented by the general formula (III)
Specific examples of the ultraviolet absorber include X ₇, X₈And X₉
Is a methyl group, X_Ten2- (2′-hydr) in which is hydrogen
Roxy-5'-methylphenyl) -4,6-dimethyl-
s-triazine, X₇, X₈, X₉And X_TenIs methyl
The group 2- (2'-hydroxy-3 ', 5'-methyl
Phenyl) -4,6-dimethyl-s-triazine and
2- (2'-hydroxy-4 ', 5'-methylpheny
) -4,6-Dimethyl-s-triazine, X₇and
X₈Is an ethyl group, X₉And X_TenIs a methyl group
2- (2'-hydroxy-3 ', 5'-methylpheny
) -4,6-Diethyl-s-triazine, X₇and
X₈Is a methyl group, X₉Is chlorine and X_TenIs hydrogen
2- (2'-hydroxy-5'-chlorophenyl
) -4,6-Dimethyl-s-triazine, X₇and
X₈Is a methyl group, X₉And X_TenIs hydrogen 2
-(2'-hydroxyphenyl) -4,6-dimethyl-
s-triazine, X₇And X ₈Is a methyl group, X
₉Is a t-butyl group, X_TenIs hydrogen 2- (2 '
-Hydroxy-5'-t-butylphenyl) -4,6-
Dimethyl-s-triazine, X₇And X₈Is phenyl
The group, X₉Is a methoxy group, X_TenIs hydrogen
2- (2'-hydroxy-4'-methoxyphenyl)-
4,6-diphenyl-s-triazine, X₇And X₈
Is a phenyl group, X₉Is an ethoxy group, X_TenBut
2- (2'-hydroxy-4'-ethoxyphen which is hydrogen
Phenyl) -4,6-diphenyl-s-triazine, X₇
And X₈Is a phenyl group, X ₉Is an isopropyl group
And X_TenIs hydrogen 2- (2'-hydroxy-
4'-isopropylphenyl) -4,6-diphenyl-
Examples thereof include s-triazine.

Benzophenone represented by the general formula (IV)
As the type dimer compound, X₁₁, X ₁₂, X₁₃And X₁₄
Is hydrogen and R is a butylene group, 1,4-bis
(4'-benzoyl-3'-hydroxyphenoxy)-
Butane, X₁₁, X₁₂And X₁₄Is hydrogen and X₁₃But water
1- (4'-benzo which is an acid group and R is a butylene group
Yl-3'-hydroxyphenoxy) -4- {4'-
(2 ″ -hydroxybenzoyl) -3′-hydroxy group
Enoxy} -butane, X₁₂And X₁₄Is hydrogen and X
₁₁And X₁₃Is a hydroxyl group and R is a butylene group
1,4-bis {4 '-(2 "-hydroxybenzoyl)
-3'-hydroxyphenoxy} -butane, X₁₁，
X₁₂, X₁₃And X₁₄Is hydrogen and R is a hexylene group
1,4-bis (4'-benzoyl-3'-hydro)
Xyphenoxy) -hexane, X₁₁, X₁₂And X₁₄But
Hydrogen and X₁₃Is a hydroxyl group, R is a hexylene group
Some 1- (4'-benzoyl-3'-hydroxypheno
Xy) -4- {4 '-(2 "-hydroxybenzoyl)
-3'-hydroxyphenoxy} -hexane, X₁₂And
And X₁₄Is hydrogen and X₁₁And X₁₃Is a hydroxyl group,
1,4-bis {4 '-(2 "-in which R is a hexylene group
Hydroxybenzoyl) -3'-hydroxyphenoxy
Si} -hexane and the like.

Since the above-mentioned ultraviolet absorber is insoluble in water, 5 to 50% by weight of the ultraviolet absorber is dispersed in water by using a dispersant to prepare a preliminary dispersion liquid, which is further physically pulverized. It is better to add it to the bath in the state of. The size of the particles is not particularly limited, but it is desirable that the particles are used after being crushed to have an average particle size of 2 μm or less.

[0021]

The reason why the fastness of sunlight of the polyester fiber dyed by the method of the present invention is greatly improved as compared with that obtained by the conventional method is that the ultraviolet absorber is internally diffused in the fiber. It is presumed that this is due to efficient adsorption to the fiber surface and blocking of ultraviolet rays near the fiber surface.

[0022]

The present invention will be further described below with reference to examples.
The particle diameters shown in the examples are values measured by a particle size distribution analyzer SALD-1100 manufactured by Shimadzu Corporation. Preparation of UV Absorber Aqueous Dispersion UV Absorber Aqueous Dispersion Example 1 2- (2′-hydroxy-3′-t-butyl-5-methylphenyl) -5-chlorobenzotriazole powder 15
0 g, Lipotol B-12 (Nikaka Chemical Co., Ltd. anion activator) 100 g, water 250 g Igarashi Machine Manufacturing Co., Ltd.
It was treated with a sand grinder made for 4 hours to obtain a fine particle dispersion having an average particle diameter of 0.42 μm.

Similarly, the following ultraviolet absorbent fine particle dispersion liquid was prepared. UV absorber aqueous dispersion example 2 2- {2'-hydroxy-3 '-(3 ", 4", 5 ",
6 ″ -tetrahydrophthalimidomethyl) -5′-methylphenyl} -benzotriazole fine particle dispersion liquid. Average particle diameter 0.43 μm. UV absorber aqueous dispersion example 3 2,2′-dihydroxy-4,4′-dimethoxybenzophenone Fine particle dispersion liquid, average particle diameter 0.43 μm, UV absorber aqueous dispersion example 4, 1,4-bis (4-benzoyl-3-oxyphenoxy) -butane fine particle dispersion liquid, average particle diameter 0.41 μm, UV absorber Aqueous Dispersion Example 5 2- (2-hydroxyphenyl) -4,6-diphenyl-s-triazine fine particle dispersion, average particle size 0.42μ
m. Example 1 Using a mini jet dyeing machine manufactured by Texum Giken Co., Ltd., a test cloth was placed in a dyeing bath containing a dye, a pH adjusting agent and a dispersion leveling agent at a dyeing bath of 130% at the following dyeing bath and bath ratio. 2 at ℃
After treating for 5 minutes, while keeping the temperature at 130 ° C, the aqueous dispersion of the ultraviolet absorber is added to this dyebath, and the mixture is further heated at 130 ° C for 5 minutes.
Processed for a minute. Then, after 10 minutes of reduction cleaning and drying,
A gray dyed product was obtained. Next, dry heat treatment was performed at 160 ° C. for 2 minutes using a pin tenter manufactured by Uenoyama Iron Works Co., Ltd. Example 2 Using a mini jet dyeing machine manufactured by Texum Giken Co., Ltd., a test cloth was placed in a dyeing bath containing a dye, a pH adjusting agent and a disperse leveling agent at a dyeing bath and bath ratio shown below. 2 at ℃
The treatment was performed for 5 minutes, and the temperature was once lowered. When the temperature reached 90 ° C, the aqueous dispersion of the ultraviolet absorber was added to the dyebath, the temperature was raised again, and the mixture was treated at 130 ° C for 5 minutes. Then, the product was reduced and washed for 10 minutes and dried to obtain a gray dyed product. Next, dry heat treatment was performed at 160 ° C. for 2 minutes using a pin tenter manufactured by Uenoyama Iron Works Co., Ltd. Comparative Example Using the mini-jet dyeing machine manufactured by Texum Giken Co., Ltd., the ultraviolet absorbent dispersion was used in the dyeing bath in the following dyeing bath and bath ratio, and the test cloth was dyed at 130 ° C. for 30 minutes.
After reducing and washing for 10 minutes, the product was dried to obtain a gray dyed product.
Then, using a pin tenter manufactured by Uenoyama Iron Works Co., Ltd., 16
A dry heat treatment was performed at 0 ° C. for 2 minutes. a) Test cloth Polyester napped product for car seats (Unit weight: 650 g / m
²⁾ b) dyeing dye bath composition CI Disperse Yellow 42 0.21% owf CI Disperse Red 302 0.08% owf CI Disperse Violet 57 0.07% owf CI Disperse Bule 60 0.11% owf CI Basic Yellow 67 0. 11% owf CI Basic Red 29 0.15% owf CI Basic Bule 54 0.40% owf Nikka Sunsalt SD-07 (Nippon Kagaku Dispersing and Leveling Agent) 0.5 g / l 90% acetic acid 0.5 g / l Ultraviolet absorbent dispersion (Examples 1, 2, 3, 4, 5) 2% owf Bath ratio 1:60 Reduction cleaning bath composition Sunmor RC-1 (Soaping agent manufactured by Nichika Kagaku Co., Ltd.) 2 g / l c) Evaluation method ( 1) Sunlight fastness A method high temperature fade odometer (manufactured by Suga Test Instruments Co., Ltd.) was used to irradiate at 83 ° C. for 400 hours (polyurethane 1 cm
backing). Then, the degree of discoloration was evaluated by a series using a discolored gray scale (JIS-0804-74) (the larger the series, the better the fastness).

Using a method B xenon fade odometer (manufactured by Suga Test Instruments Co., Ltd.), irradiation was performed at 89 ° C. for 3.8 hours, and then at 38 ° C., 1 hour in darkness for 1 cycle was operated for 50 cycles (integrated radiation). Illuminance 110000KJ / m ² , polyurethane 1cm lining). Then, the degree of discoloration was evaluated by a series using a discolored gray scale (JIS-0804-74) (the larger the series, the better the fastness). d) Results The obtained results are shown in Tables 1 and 2 below.

[0025]

[Table 1]

[0026]

[Table 2]

Claims (1)

[Claims] 1. When dyeing a fiber material composed of a polyester fiber or a mixed fiber of a polyester fiber and another fiber, the fiber material is put into a dye bath and the dye bath is set to 100.
After the temperature is raised to a temperature of 140 ° C., at least one water dispersion liquid selected from the ultraviolet absorbers represented by the following general formulas (I) to (IV) is added while maintaining this temperature, and 1
Treatment is carried out at 20 to 140 ° C. for 5 to 30 minutes, or after the dyeing bath is heated to a temperature of 100 to 140 ° C., the temperature is once lowered, and then the UV absorption represented by the following general formulas (I) to (IV) is absorbed. A method for dyeing a polyester fiber, which comprises adding at least one aqueous dispersion selected from the agents, heating again, and treating at 120 to 140 ° C. for 5 to 30 minutes. [Chemical 1] [Chemical 2] In the above formula, X ₁ , X ₂ , X ₃ , X ₄ , X ₅ and X ₆ are
Each independently, hydrogen, halogen, hydroxyl group, carbon number 1 ~
8 represents an alkyl group, an aryl group, a benzyl group, an alkoxy group, an aryloxy group, a benzyloxy group or a tetrahydrophthalimidomethyl group. [Chemical 3] In the above formula, X ₇ and X ₈ are each independently hydrogen, halogen, hydroxyl group, alkyl group having 1 to 8 carbon atoms, aryl group, benzyl group, alkoxy group, aryloxy group, benzyloxy group, amino group, Represents an aminoalkyl group or an aminoaryl group, and X ₉ and X ₁₀ each independently represent hydrogen, halogen, a hydroxyl group, an alkyl group having 1 to 8 carbon atoms, an aryl group, a benzyl group, an alkoxy group or an aryloxy group. . [Chemical 4] In the above formula, R represents an alkylene group having 1 to 8 carbon atoms, and X ₁₁
And X ₁₃ each independently represent hydrogen or a hydroxyl group, and X ₁₂ and X ₁₄ are each independently hydrogen, halogen, a hydroxyl group, an alkyl group having 1 to 8 carbon atoms, an aryl group,
It represents a benzyl group, an alkoxy group or an aryloxy group.