JPH08218278A - Disperse leveling agent for dyeing polyester fiber - Google Patents

Abstract

PURPOSE: To obtain a disperse leveling agent consisting of specific ether compound(s), capable of uniformly dyeing polyester fibers through its addition to a high-temperature dyeing bath for such fibers irrespective of the pH level of the dyeing bath. CONSTITUTION: This disperse leveling agent consists of at least one kind of compound selected from ether compounds of formula I [(m) is an integer of 0-5; (n) is 2 or 3; R<1> is a 6-12C alkyl, cycloalkyl, phenyl, benzyl or α- methylbenzyl; when (n) is 2, A is a dioxane group derived from ethylene glycol, propylene glycol or polyalkylene glycols <=4000 in molecular weight; when (n) is 3, A is a trioxy group of formula II or III (R<2> is a 2C or 3C alkylene; (a), (b), (c), (d), (e) and (f) are each an integer of 0-50, and (a+b+c) is 0-50, and (d+e+f) is 0-50]. This agent is added to a polyester fiber dyeing bath containing a disperse dye to conduct a high-temperature dyeing of the polyester fibers.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a disperse dyeing agent for dyeing polyester fibers and a method for dyeing polyester fibers using the same. More specifically, the present invention is an ether type dispersion level agent that enables stable dispersion of dyes in a dyeing bath and uniform dyeing evenly when dyeing polyester fiber materials at high temperature using disperse dyes. The present invention relates to a dye and a method for dyeing a polyester fiber material using the dye.

[0002]

2. Description of the Related Art Conventionally, high-temperature dyeing of polyester fibers with a disperse dye is generally carried out at a pH of 4 to 6 in a weakly acidic range,
It is carried out at a high temperature of 0 to 140 ° C., and in order to prevent the dye from agglomerating and to dye uniformly without spots, a dispersion leveling agent is always added to the dyeing bath. Here, as the dispersion leveling agent which has been conventionally used, an aliphatic alcohol, a mono-penta (α-methylbenzyl) phenol, a compound obtained by adding ethylene oxide to an alkylphenol, etc. Many of these are ester type compounds consisting of ester derivatives formed by the reaction (Japanese Patent Laid-Open No. 53-70175).

However, in recent years, in order to eliminate the one-bath scouring dyeing for labor saving of the process and the dyeing troubles caused by the polyester oligomer, so-called dyeing is performed at a high temperature of 120 to 140 ° C. in an alkaline range of pH 8 or more. Alkali dyeing is performed. When a conventional ester-type dispersion leveling agent is used under such dyeing conditions, the ester group is hydrolyzed, and the conventional leveling effect is reduced, and the aliphatic carboxylic acid produced by the decomposition causes dye aggregation and the like. Is causing the trouble of. Therefore, in the recent alkali dyeing, it is not preferable to use the conventional ester-type dispersion leveling agent.

[0004]

DISCLOSURE OF THE INVENTION The present invention solves the drawbacks of conventional ester-type disperse and leveling agents in high-temperature dyeing of polyester fibers using disperse dyes, not to mention dyeing in acidic regions. It is an object of the present invention to provide a disperse-leveling agent and a dyeing method that prevent dye aggregation even in dyeing in an alkaline region and enable uniform dyeing without spots.

[0005]

The inventors of the present invention have conducted extensive studies to solve the above problems, and as a result, when a polyester fiber is dyed at high temperature using a disperse dye, a compound having a specific ether structure It has been found that it has an excellent dispersion leveling effect, and, surprisingly, such an ether compound can be effectively used without being hydrolyzed even in alkaline dyeing in which high temperature dyeing is performed in an alkaline range of pH 8 or more. The inventors have found that the dispersion and leveling effect is maintained, and completed the present invention.

Accordingly, the present invention provides one or more compounds selected from the ether compounds represented by the following general formula (1), which are useful for high temperature dyeing of polyester fiber materials using a disperse dye. Disclosed is a dispersion leveling agent for dyeing polyester fibers.

[0007]

[Chemical 4]

[In the above formula, m is an integer of 0 to 5, n is 2 or 3, and R ¹ is an alkyl or cycloalkyl group having 6 to 12 carbon atoms, a phenyl group, a benzyl group or α-methyl. Represents a benzyl group, when n is 2, A represents a dioxy group derived from ethylene glycol, propylene glycol or polyalkylene glycol having a molecular weight of 4000 or less, and when n is 3, A represents the following general formula (2) Or (3)

[0009]

Embedded image

[0010]

[Chemical 6]

(In the above formula, R ² represents an alkylene group having 2 or 3 carbon atoms, a, b, c, d, e and f are each an integer of 0 to 50, and a + b + c is 0 to 50. And d + e + f is 0 to 50) represents a trioxy group represented by the present invention] The present invention also provides a compound represented by the general formula (1) when dyeing a polyester fiber material at a high temperature using a disperse dye. The present invention provides a method for dyeing polyester fibers, which comprises adding one or more of the above to a dye bath.

In the compound of the general formula (1), the substituent R
Examples of the alkyl group of ¹ include a hexyl group, a cyclohexyl group, an octyl group, a nonyl group, and a lauryl group. When m is 2 or more, all the substituents R ¹ do not have to be the same and may be different groups. The dioxy group of A includes ethylene glycol and propylene glycol, and polyalkylene glycols such as diethylene glycol, triethylene glycol, polyethylene glycol having a molecular weight of 4000 or less, dipropylene glycol, tripropylene glycol, and polypropylene glycol having a molecular weight of 4000 or less. And a dioxy group derived from polyalkylene glycol or the like obtained by a random or block addition reaction of ethylene oxide and propylene oxide having a molecular weight of 4000 or less. Examples of the trioxy group of the general formula (2) include trioxy groups derived from glycerin and compounds obtained by adding ethylene oxide, propylene oxide or a mixture of ethylene oxide and propylene oxide to glycerin, and the general formula (3) Examples of the trioxy group include trimethylolpropane and those derived from trimethylolpropane with a compound obtained by adding ethylene oxide, propylene oxide, or a mixture of ethylene oxide and propylene oxide.

The ether-type dispersion leveling agent of the present invention can be easily obtained by the synthetic method described below. That is, a Lewis acid catalyst (for example, boron trifluoride ether complex salt) is added to an alcohol corresponding to the oxy group of A in the general formula (1), and this alcohol is reacted with an equivalent amount of epichlorohydrin. Then, the above alcohol and an equivalent amount of phenol or a phenol derivative having a substituent on the aromatic ring, and 1.1 times equivalent amount of sodium hydroxide of the phenol or phenol derivative are added and reacted. Thereby, the target compound can be obtained in high yield.

The compounds represented by the following general formulas (4) and (5), which are similar to the compound represented by the general formula (1), also have the same effects as the dispersion leveling agent of the present invention.

[0015]

[Chemical 7]

[0016]

Embedded image

[In the above formula, R ³ O- represents an alkoxy group (including a group derived from an ethylene oxide or propylene oxide adduct of alcohol, phenol or a phenol derivative), n is 2 or 3, and
A represents the same as defined in the general formula (1)] However, in the production of the compounds of the general formulas (4) and (5), the reaction rate is lowered because they are all synthesized by induction from alcohol. It is not realistic because it has drawbacks such as

The dispersion leveling agent of the present invention can be used not only in the case of using the compound alone, but also after emulsifying and dispersing the above dispersion leveling agent compound in water by appropriately using a surfactant having another structure. . The amount of the dispersion leveling agent of the present invention, as a simple substance of the compound, is usually in the range of 0.1 to 4 g / l, preferably in the range of 0.2 to 2 g / l in the dyeing bath.

The polyester fibers useful in the present invention may be polyester fibers alone or may be in the form of composite fibers composed of polyester fibers and other fibers,
Further, it may be in any form such as a woven fabric, a knitted fabric, a non-woven fabric, loose fibers and threads. Dyeing can be carried out under pressure at a temperature of 120 to 140 ° C., as in the case of dyeing polyester fibers with a disperse dye. The pH of the dyeing bath may be in a wide range from an acidic range of pH 4 to an alkaline range of pH 8 or higher. In particular, in the dyeing method of the present invention, even in an alkaline region of pH 8 or higher, the dispersion leveling action is maintained, and an excellent effect that a uniform dyed product is obtained can be achieved.

[0020]

It is considered that the dispersion leveling agent according to the present invention can maintain stable dispersion leveling property because of the chemical structure of the compound used. That is, the compound used in the conventional dispersion leveling agent has a structure having an ester group having poor chemical stability, whereas the dispersion leveling agent compound of the present invention is composed of an ether bond which is chemically stable. And does not have an ester group.

[0021]

The present invention will be described in more detail with reference to the following examples, but the present invention should not be limited to these examples. Example 1 30 g of polyethylene glycol having an average molecular weight of 1500
0.3 g of boron trifluoride ethyl ether complex salt is added to (0.02 mol), and the temperature is raised to 70 ° C. under a nitrogen gas stream. 3.7 g (0.04 mol) of epichlorohydrin was added dropwise, and the mixture was reacted at 80 to 90 ° C for 2 hours. Then, 24.6 g of penta (α-methylbenzyl) phenol (0.
04 mol) and 1.76 g (0.0
44 mol) was added, and the mixture was reacted at 90 to 110 ° C. for 3 hours to obtain a dispersion leveling agent composed of the compound described below. The reaction rate was 91%. The reaction rate is obtained by measuring the chloride ion concentration in the reaction system by the Mohr method (method described in Experimental Chemistry Lecture 15, edited by The Chemical Society of Japan) and by the following equation. Reaction rate (%) = (Actually measured chloride ion concentration / Theoretical chloride ion concentration at the time of 100% reaction) × 100 Example 2 Pluronic L-64 which is an ethylene oxide adduct of polypropylene glycol (average molecular weight of about 2900)
To 58 g (0.02 mol) of Asahi Denka Co., Ltd., 0.3 g of boron trifluoride ethyl ether complex salt is added, and the temperature is raised to 70 ° C. under a nitrogen gas stream. Epichlorohydrin 3.
7 g (0.04 mol) is added dropwise and reacted at 80 to 90 ° C. for 2 hours. Then penta (α-methylbenzyl)
24.6 g (0.04 mol) of phenol and 1.76 g (0.044 mol) of sodium hydroxide are added, 90
The reaction was carried out at ˜110 ° C. for 3 hours to obtain a dispersion leveling agent composed of the compound described below. The reaction rate determined in the same manner as in Example 1 was 89%.

Examples 3 to 10 Example 3 was repeated by repeating the same operations as in Examples 1 and 2.
Synthesis of 10 was performed. Table 1 below shows the alcohols, phenol derivatives and their reaction molar amounts that were subjected to the reaction in these Examples.

[0023]

[Table 1]

The structural formulas of the compounds obtained in Examples 1 to 10 are shown below. Example 1

[0025]

[Chemical 9]

Example 2

[0027]

[Chemical 10]

Example 3

[0029]

[Chemical 11]

Example 4

[0031]

[Chemical 12]

Example 5

[0033]

[Chemical 13]

Example 6

[0035]

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Example 7

[0037]

[Chemical 15]

Example 8

[0039]

Embedded image

Example 9

[0041]

[Chemical 17]

Embodiment 10

[0043]

Embedded image

In the above formula, PO is a propyleneoxy group and MB is an α-methylbenzyl group. Performance Test Examples The dispersion leveling agents obtained in Examples 1 to 10 and the oleic acid ester of penta (α-methylbenzyl) phenol ethylene oxide adduct (addition mole number 30 mol) as comparative examples were subjected to the following tests. .

In Examples 1, 2, 6, 7 and Comparative Example, the compound was used alone as a dispersion leveling agent, and
In 5 and 8 to 10, a nonionic surfactant consisting of penta (α-methylbenzyl) phenol ethylene oxide adduct (addition mole number 30 moles) was added to each compound in an amount of 2
The compound added in an amount of 0% by weight and emulsified with water was used as the compound alone so that a predetermined amount was obtained.

Further, the test dyeing bath for performance test is set to pH 4
Tests were conducted under two conditions (adjusted with acetic acid) and pH 10 (adjusted with sodium hydroxide). Performance test method 1. Dispersibility test (color pet winding method) The following dyeing solution was put into a color pet (manufactured by Nippon Dyeing Machine) pot, and a polyester processed yarn knit was wound on a holder,
Set the both ends stopped by O bands, rapidly raise the temperature to 115 ° C. for dyeing, and immediately cool. After lightly washing the knit with water, the dispersibility is evaluated based on the number of casing spots due to the aggregation of the dye.

Dyes: C.I. I. Disperse Red 167 3% owf Dispersing and leveling agent: 0.5 g / liter Bath ratio: 1:20 (Evaluation): ○ No casing spot △ There is a slight casing spot × There is a considerable casing spot 2. Level dyeing test A polyester knitted yarn knit dyed under the following conditions and an undyed polyester yarn knitted knit are placed in an aqueous solution containing a disperse leveling agent at a ratio of 1: 1 and treated at 130 ° C for 5 minutes in a color pet. Perform and compare how much the dye in the dyed knit transferred to the undyed knit.

Dyeing conditions for dyeing knit Dyes: C.I. I. Disperse Red 127 3% owf acetic acid: 0.3 cc / l bath ratio: 1:20 Temperature × time: 130 ° C. × 30 minutes levelness test conditions dispersing leveling agent: 0.5 g / liter bath ratio: 1:20 (Evaluation) The dye-dyeing density (K / S value) of the transfer dyed knit (dyed knit) and the transfer dyed white knit (undyed knit) obtained in the above level dyeing test was measured by Macbeth spectrophotometer. Total M
S-2020 was measured, and the migration rate was calculated by the following formula. The higher the number, the better the level dyeing property.

Transfer rate = {(K / S value of transfer white knit) /
(K / S value of transfer dyed knit)} × 100 The performance test results are summarized in Table 2.

[0050]

[Table 2]

[0051]

By using the disperse-leveling agent of the present invention, a stable disperse-leveling effect can be obtained in high-temperature dyeing of polyester fibers with a disperse dye, regardless of whether it is dyed in acidic areas or dyed in alkaline areas.

Claims (3)

[Claims] 1. A polyester fiber dyeing containing one or more compounds selected from an ether compound represented by the following general formula (1), which is useful for dyeing a polyester fiber material at a high temperature using a disperse dye. Dispersing and leveling agent. Embedded image [In the above formula, m is an integer of 0 to 5, n is 2 or 3, and R ¹ is an alkyl or cycloalkyl group having 6 to 12 carbon atoms, a phenyl group, a benzyl group or an α-methylbenzyl group. When n is 2, A is ethylene glycol, propylene glycol, or has a molecular weight of 4000.
Represents a dioxy group derived from the following polyalkylene glycol, and when n is 3, A is represented by the following general formula (2) or (3): Embedded image (In the above formula, R ² represents an alkylene group having 2 or 3 carbon atoms, a, b, c, d, e and f are each an integer of 0 to 50, a + b + c is 0 to 50, and d + e +
f represents a trioxy group represented by 0 to 50] 2. When the polyester fiber material is dyed at high temperature using a disperse dye, the compound of claim 1 is used.
A method for dyeing polyester fibers, which comprises adding one or more kinds to a dye bath. 3. The method according to claim 2, wherein the dyeing is performed in an alkaline area.