JPH09217276A - Treating agent for hydrophobic fiber and improvement in color fastness to light of hydrophobic fiber using the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To improve the color fastness to light of a dyed product of a hydrophobic fiber by applying a treating agent containing an ultraviolet absorber of a specific structure and a dispersing agent therein to the hydrophobic fiber. SOLUTION: This treating agent for a hydrophobic fiber comprises 5-50wt.%, preferably 10-40wt.% compound, represented by the formula (R1 is a 1-12C alkyl or cumyl; R2 is hydroxy, a 1-12C alkoxy or benzyloxy; R3 is H, hydroxy or a 1-12C alkoxy; R4 is H or hydroxy; X is H or chlorine) and blended with 5-50wt.%, preferably 10-40wt.% sulfonate type anionic surfactant such as a formalin condensate of sodium naphthalenesulfonate, 0-25wt.%, preferably 0-20wt.% polyoxyalkylene type nonionic surfactant such as ethylene oxide adduct to polypropylene glycol and its fatty acid ester and 0-25wt.%, preferably 0-20wt.% water-soluble polymer such as polyvinyl alcohol. The resultant treating agent is added to a dye bath for a polyester fiber to treat the polyester fiber in the same bath.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a treatment agent for hydrophobic fibers and a method for improving the light fastness of hydrophobic fibers using the same. More specifically, it relates to a treating agent for improving the light resistance of hydrophobic fibers, especially polyester fibers, which are dyed with a disperse dye, a cationic dye or the like.

[0002]

2. Description of the Related Art In recent years, hydrophobic fibers dyed with disperse dyes or cationic dyes have come to be widely used in fields where there is a lot of opportunity to be exposed to natural light for a long time, such as a sheet or a sheet of caten. . As described above, when exposed to natural light for a long time, fading of the dyed product due to light is remarkable over time, which is a serious problem in use. Of course, studies are underway to increase the light fastness of the dye itself used for dyeing, but the effect is not always sufficient, and it is difficult to improve the light resistance of dyes having a wide hue. is there. As one method for solving this problem, an ultraviolet absorber is used in combination during dyeing.

As an example, in dyeing, a benzotriazole-based light fastness improver (eg, 2- (2'-hydroxy-3'-t-butyl-5'-methylphenyl) -5) is used.
-Chlorobenzotriazole) is known (JP-A-2-41468 and JP-A-4-3516).
It is widely used in the dyeing industry. However, with some dyes, the treatment with this light fastness improver causes a problem that the light fastness is rather decreased.
Furthermore, this light fastness improver has a poor sublimation fastness, so
There is a problem that when the dyed product is heated in the tosset process or the like, it is sublimated and its effect is lost.

On the other hand, it is known that a benzophenone compound, which is known as a compound having a property of absorbing ultraviolet rays, is used as a light fastness improving agent (Japanese Patent Application Laid-Open No. Sho 5).
9-223379, JP-A-59-157881, JP-A-1-287189, etc.). However, since this light fastness improver generally has a low affinity for hydrophobic fibers, it is difficult to impart it to the fibers during dyeing. This means that the ultraviolet absorption effect is not good, that is, the light resistance improving effect is poor. Therefore, although the benzophenone-based light fastness improver is superior in sublimation fastness to the benzotriazole-based, it is hardly used as a fiber treating agent.

Although a method of using a benzotriazole compound and a benzophenone compound in combination has been proposed (Japanese Patent Laid-Open No. 4-339885, etc.), it does not lead to a fundamental solution to the above problems.

Further, a method using an s-triazine compound has been disclosed (Japanese Patent Laid-Open No. 4-239581, etc.), but the sublimability has been improved, but the affinity for hydrophobic fibers is still insufficient.

[0007]

SUMMARY OF THE INVENTION A treatment agent for improving light fastness, which has a sufficient affinity for hydrophobic fibers and a sufficiently high sublimation fastness, is desired.

[0008]

The inventor of the present invention has achieved the present invention as a result of extensive studies to solve the above-mentioned conventional drawbacks.

That is, the present invention is based on the following equation (1):

[0010]

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(Wherein R ₁ is a linear or branched alkyl group having 1 to 12 carbon atoms or a cumyl group, and R ₂ is a hydroxy group or a linear or branched alkoxy group having 1 to 12 carbon atoms, or benzyl. An oxy group, R ₃ is a hydrogen atom, a hydroxy group or a linear or branched alkoxy group having 1 to 12 carbon atoms, R ₄ is a hydrogen atom or a hydroxy group, and X is a hydrogen atom or a chlorine atom. .) A treatment agent for hydrophobic fibers containing a compound and a dispersant (2) The dispersant is a group consisting of a sulfonate type anionic surfactant, a polyoxyalkylene type nonionic surfactant and a water-soluble polymer. 1 to 3 kinds of hydrophobic fiber treating agent according to the above item (1) (3) Hydrophobic fiber characterized by using the hydrophobic fiber treating agent according to the above item (1) or (2) For lightfastness Regarding the law.

[0012]

BEST MODE FOR CARRYING OUT THE INVENTION The present invention will be described in detail below.
In the compound represented by the formula (1) used in the present invention, R ₁ represents a linear or branched alkyl group having 1 to 12 carbon atoms or a cumyl group, and a linear or branched chain having 1 to 12 carbon atoms. Specific examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a neopentyl group, and a tert-group.
Pentyl group, n-hexyl group, isohexyl group, 2-ethylhexyl group, heptyl group, n-octyl group, isooctyl group, tert-octyl group, 1,1,3,3-tetramethylbutyl group, n-nonyl group, Examples thereof include isononyl group, decyl group, undecyl group, octadecyl group and dodecyl group. R ₂ is a hydroxy group or has 1 carbon atom
~ 12 straight or branched chain alkoxy groups, benzyloxy group, R ₃ represents a hydrogen atom, a hydroxy group or a straight or branched chain alkoxy group having 1 to 12 carbon atoms,
Specific examples of the linear or branched alkoxy group having 1 to 12 carbon atoms in R ₂ and R ₃ include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group,
Examples thereof include a hexyloxy group, a heptyloxy group, an octyloxy group, a nonyloxy group, a decyloxy group, an undecyloxy group and a dodecyloxy group. R ₄ represents a hydrogen atom or a hydroxy group, and X represents a hydrogen atom or a chlorine atom. The compound of formula (1) used in preparing the treating agent of the present invention is known, and can be easily obtained by a known production method (Japanese Patent Laid-Open Publication No. H6 (1994) -63242).
-321918).

Further, as the dispersant used in the present invention, a general dispersant used for making fine particles (dispersion) of a disperse dye is used, but a preferable one is a sulfonate type anion interface. Activators and polyoxyalkylene type nonionic surfactants are mentioned. As a specific example of the sulfonate type anionic surfactant that can be used, any surfactant can be used as long as it has one or more sulfonic acid groups. Examples thereof include a formalin condensate of sodium naphthalene sulfonic acid salt, a formalin condensate of a special aromatic sulfonic acid soda salt, an alkylbenzene sulfonate, an alkylnaphthalene sulfonate, and the like. Among these, preferred are formalin condensates of sodium naphthalene sulfonic acid salts and formalin condensates of special aromatic sulfonic acid soda salts.

Specific examples of the polyoxyalkylene type nonionic surfactant that can be used include nonionic surfactants of the type in which alkylene oxide is added to alcohols, phenols, amines and the like. Although any of these can be used, specific examples of such polyoxyalkylene type nonionic surfactants include higher alcohol alkylene oxide adducts, alkylphenol alkylene oxide adducts, and fatty acid alkylene oxide adducts. , Polyhydric alcohol fatty acid ester alkylene oxide adducts, higher alkylamine alkylene oxide adducts, polypropylene glycol ethylene oxide adducts and fatty acid esters thereof. Of these, preferred are higher alcohol alkylene oxide adducts, polypropylene glycol ethylene oxide adducts and fatty acid esters thereof,
Particularly preferred are polypropylene glycol ethylene oxide adducts and fatty acid esters thereof.

Other dispersants that can be used in the treatment agent of the present invention include water-soluble polymers. Specific examples of the water-soluble polymer include polyvinyl alcohol, polyacrylic acid ester emulsion, methyl cellulose, hydroxymethyl cellulose and hydroxyethyl cellulose.
Examples thereof include polyvinyl alcohol and carboxymethyl cellulose, and polyvinyl alcohol is preferable.

The above sulfonate type anionic surfactants, polyoxyalkylene type nonionic surfactants and water-soluble polymers may be used alone or in combination.

The treatment agent for hydrophobic fibers of the present invention is prepared by using the compound represented by the formula (1), a dispersant and the like, for example, by the following method. Water is 20 to 80% by weight, the compound of formula (1) is usually 5 to 50% by weight, preferably 10 to 40% by weight, and the sulfonic acid type anionic surfactant is usually 5 to 50% by weight, preferably 10 to 40%. weight%,
The polyoxyalkylene type nonionic surfactant is usually 0 to
25% by weight, preferably 0 to 20% by weight, and 0 to 25% by weight, preferably 1 to 20% by weight of another dispersant are mixed and finely divided (dispersed) with a sand grinder or the like. A particle size of several microns is usually sufficient, but the particle size may be reduced to about 1/10 of the particle size depending on the application. At this time, if necessary, additives such as a non-drying agent, a defoaming agent, and a thickener can be added. Further, the treatment agent for hydrophobic fiber of the present invention may be used in a liquid state, but may also be used in a powder state after being dried with a spray dryer or the like.

In the actual use, the treating agent of the present invention is used in the form of being diluted with water when it is in a liquid state, and when being dispersed in water when it is a dried product. When using the treating agent of the present invention, the concentration of the compound of formula (1) in water is usually 0.1 to 20% ow.
f (relative to fiber weight), preferably 0.1 to 10% owf, and if less than 0.1%, the effect of improving light resistance is insufficient. Conversely, if it is more than 10% owf, light resistance is improved. The effect is not so great as compared with the case of 10% owf or less, which is uneconomical.

The improvement method of the present invention is achieved by applying the treatment agent of the present invention to fibers. As a method of applying the treatment agent of the present invention to the fiber, a method of treating the fiber with the treatment agent in advance before dyeing, a method of treating the fiber with the treatment agent together with a dye at the time of dyeing, a method after dyeing Examples thereof include a method of treating fibers with a treating agent. Of these,
A preferred method is to treat the fiber with the dye during dyeing.
When the treatment agent of the present invention is applied by the dipping method or the thermosol method, the treatment agent of the present invention is added to the dye bath together with the dye. When the printing method is used, the treatment agent of the present invention is added to the color paste. For example, in the case of a polyester fiber dip dyeing method, 100 to 100
Usually 10 to 60 minutes at 135 ° C, 1 in the case of the thermosol method
Usually 30 to 120 seconds at 50 to 210 ° C., 160 to 190 by HT method (normal temperature high temperature steaming method) in the case of printing method.
Usually 5 to 10 minutes at 110 ° C., 110 to 130 ° C. at 20 to 40 minutes by HP method (high pressure steaming method), and 1 at dipping method in the case of acidified polyester fiber (abbreviated as CDP fiber).
It is usually 10 to 90 minutes at 00 to 120 ° C., usually 30 to 120 seconds at 150 to 200 ° C. in the thermosol method, and 120 to 160 usually 5 to 10 minutes in the HT method in the case of the printing method.
In the method, it is usually 10 to 30 minutes at 100 to 120 ° C.
Further, in order to pretreat the fibers with the treatment agent of the present invention before dyeing, 100 to 135 under pressure in an aqueous medium in which the fibers are immersed.
It is preferable to carry out the treatment usually at 10 ° C for 10 to 60 minutes.

When the treating agent of the present invention is applied to fibers, it can be used in combination with various agents depending on the method. For example, a refining agent when treated before dyeing, a leveling agent, an antifoaming agent or the like in addition to the dye in the case of the dip dyeing method, and a sizing agent or the like in addition to the dye in the case of the thermosol method. When used, they are various finishing agents and the like.

Specific examples of the hydrophobic fibers to which the treating agent of the present invention can be applied include polyester fibers, acetate fibers, polyamide fibers and aramid fibers. That is, polyester fibers such as polyethylene terephthalate, polyethylene terephthalate / isophthalate, polyethylene terephthalate / paraoxybenzoate, polyethylene terephthalate / polybutylene terephthalate, and acidified polyester. And acetate fibers such as diacetate and triacetate, polyamide fibers such as nylon 66 and nylon 6, aramid fibers such as poly (m-phenylene isophthalamide) and poly (p-phenylene terephthalamide), and Examples include mixed spinning of these fibers with other natural fibers, semi-synthetic fibers, synthetic fibers, and interwoven fabrics. It should be noted that the treating agent of the present invention has the same improvement effect on polyester fibers and polyamide fibers such as nylon. That is, even when applied to a blended product of these different fibers, the same and good effect of improving light resistance can be obtained for both fibers.

The treatment agent of the present invention is uniformly dispersed in the treatment liquid, has excellent emulsion stability, and has a sufficiently high affinity for the hydrophobic fiber, so that it uniformly diffuses and permeates into the hydrophobic fiber. Therefore, the treating agent of the present invention is a polyester fiber,
By using it for hydrophobic fibers such as acetate fibers and nylon, the light resistance of these hydrophobic fibers dyed with a disperse dye or a cationic dye can be remarkably improved. Further, since the compound of formula (1) in the treatment agent of the present invention has high fastness to sublimation, the effect of improving light resistance does not deteriorate even by heat treatment such as heat setting.

[0023]

EXAMPLES The present invention will be described more specifically with reference to examples, but the present invention is not limited to these examples. In the examples, "parts" and "%" are "parts by weight" and "% by weight", respectively.

Example 1 15 parts of a compound of the following formula (2),

[0025]

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Demol N (trade name, formalin condensate of sodium naphthalenesulfonic acid salt, manufactured by Kao Corporation) 15
Part, Levenol DT-400 (trade name, polypropylene glycol ethylene oxide adduct, manufactured by Kao Corporation)
1 part, non-drying agent (glycerin) 5 parts, goshenol GL
-05 (trade name, polyvinyl alcohol 25% aqueous solution,
4 parts of Nippon Synthetic Chemical Industry Co., Ltd., several drops of an antifoaming agent, and 60 parts of water were wet pulverized using a sand grinder (6 hours) to obtain a sufficiently finely treated treatment agent of the present invention.

Example 2 15 parts of a compound of the following formula (3),

[0028]

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Demol C (trade name, formalin condensation product of soda salt of special aromatic sulfonic acid, manufactured by Kao Corporation) 15
, 5 parts of Goshenol GL-05, 5 parts of non-drying agent (glycerin), a few drops of defoaming agent, and 61 parts of water are wet pulverized using a sand grinder (5 hours) to form fine particles. The processed treating agent of the present invention was obtained.

Example 3 15 parts of a compound of the following formula (4)

[0031]

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Demol SNB (trade name, formalin condensate of β-naphthalene sulfonic acid soda salt, Kao Corporation)
15 parts, Lebenol DT-400 3 parts, non-drying agent (glycerin) 10 parts, a few drops of antifoaming agent, and 57 parts of water were microparticulated using a sand grinder to give the treatment agent of the present invention. Obtained.

Example 4 15 parts of a compound of the following formula (5),

[0034]

[Chemical 6]

Demol N 15 parts, Demol C 5 parts,
5 parts of a non-drying agent (glycerin), a few drops of a defoaming agent, and 60 parts of water were wet-milled using a sand grinder (6 hours) to obtain a sufficiently finely treated treatment agent of the present invention.

Example 5 15 parts of a compound of the following formula (6),

[0037]

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30 parts of Gosenoll GL-05, 5 parts of a non-drying agent (glycerin), a few drops of an antifoaming agent, and 50 parts of water were wet-milled using a sand grinder (6 hours) to obtain fine particles. Thus, the treated agent of the present invention was obtained.

Examples 6 to 22 The following general formula (7) synthesized by a known method

[0040]

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Represented by X, R ₁ , R ₂ , R ₃ and R ₄
Was used in place of the compound of formula (2) or formula (3) of Example 1 or Example 2 in the same manner as described above, but the compound having the structure shown in Table 1 below was treated in the same manner to obtain the treatment agent of the present invention. Obtained.

[0042]

Table 1 Table 1 Example X R ₁ R ₂ R ₃ R ₄ 6 H methyl n-octyloxy H H 7 H methyl sec-octyloxy H H 8 Cl methyl n-octyloxy H H 9 H methyl octadecyloxy H H10H Methyl dodecyloxy HH11H t-butyl methoxy HH12H t-pentyl methoxy HH13H t-octyl methoxy HH14H t-octyl isooctyloxy HH15Cl t-octyl hydroxy HH 16 H t-octyl n-octyloxy H H 17 H methyl benzyloxy H H 18 H 1-methyl-1 methoxy H H-phenylethyl (cumyl) 19 H 1,1,3,3-methoxy H H tetramethylbutyl 20 H t-octyl methoxy methoxy hydroxy 21 H t-oct Cyl hydroxy hydroxy hydroxy 22 H t-octyl methoxy H hydroxy

Example 23 Application to polyester fiber and results of light resistance test (dipping method) (1) Treatment agent (a) Treatment agent of the present invention (obtained in Example 1) (b) Commercially available benzotriazole System (2- (2'-hydroxy-3'-t-butyl-5'-methylphenyl)-
5-Chloro-benzotriazole) treating agent (preparation of treating agent was in accordance with Example 1)

(2) Processing conditions (a) Dye: The following three types of dyes were mixed and dyed (brown color). Kayaron Polyester Yellow AUL-S (trade name, disperse dye, manufactured by Nippon Kayaku Co., Ltd.) 0.38% owf Kayaron Polyester Red AUL-S (trade name,
Disperse dye, manufactured by Nippon Kayaku Co., Ltd. 0.12% owf Kayaron Polyester Blue AUL-S (trade name,
Disperse dye, manufactured by Nippon Kayaku Co., Ltd. 0.39% owf (b) Acetic acid 0.7 g / l (c) Sodium acetate 1.0 g / l (d) Each treatment agent of (1) 4.0% owf (E) Bath ratio 1:30 (F) Test cloth Polyester processed yarn fabric (G) Dyeing (treatment) conditions 130 ° C, 60 minutes

(3) Light fastness test (accelerated irradiation test) conditions For the dyed cloth prepared under the above conditions and the dyed cloth dyed without using the treating agent, a thickness of 1 is provided between them and the panel.
Irradiation was carried out with a carbon fade meter under the conditions of 83 ° C. and 200 hours with a 0 mm urethane foam sandwiched therebetween. The irradiated cloth and the non-irradiated cloth were checked with a JIS discoloring gray scale, and the results are shown in Table 2 as light fastness.

(4) Sublimation resistance test For each dyed fabric obtained in (2) of Example 23, 1
Heat setting was carried out at 80 ° C. for 1 minute, and the same light fastness test was performed on the dyed cloth before heat set and the dyed cloth after heat set. The results are also shown in Table 2.

[0047]

[Table 2] Table 2 Light-proof and no-hardness additive Processing agent of the present invention (a) Commercially available processing agent (b) Grade 3 to 4 Grade 3 (without heat setting) Grade 3 to 4 Grade 2 ( 〃)

As shown in Table 2, the effect of improving the light fastness of the treating agent of the present invention is recognized. Further, the treatment agent of the present invention has a higher effect of improving the light fastness than the commercially available benzotriazole type light fastness improver. Further, it was confirmed that the light fastness was not deteriorated by the heat treatment, and the light fastness was strong.

[0049]

EFFECT OF THE INVENTION A treatment agent for hydrophobic fibers having a high affinity for hydrophobic fibers and having a high sublimation resistance for improving the fastness to sunlight was obtained.

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁶ Identification code Internal reference number FI Technical display location D06P 5/06 DBC D06P 5/06 DBC DBG DBG

Claims (3)

[Claims] (1) Formula (1) (In the formula, R ₁ represents a linear or branched alkyl group having 1 to 12 carbon atoms or a cumyl group, and R ₂ represents a hydroxy group, a linear or branched alkoxy group having 1 to 12 carbon atoms, or a benzyloxy group. , R ₃ is a hydrogen atom, a hydroxy group or a linear or branched alkoxy group having 1 to 12 carbon atoms, R ₄
Represents a hydrogen atom or a hydroxy group, and X represents a hydrogen atom or a chlorine atom. ) A treatment agent for hydrophobic fibers, which comprises a compound represented by the formula (4) and a dispersant. 2. The hydrophobicity according to claim 1, wherein the dispersant is 1 to 3 kinds selected from the group consisting of a sulfonate type anionic surfactant, a polyoxyalkylene type nonionic surfactant and a water-soluble polymer. Textile treatment agent. 3. A method for improving light fastness of hydrophobic fibers, which comprises using the treatment agent for hydrophobic fibers according to claim 1 or 2.