JP3303000B2 - Penetrant for alkali weight reduction processing of polyester fiber - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a penetrating agent for reducing the alkali content of polyester fibers, and more particularly, to promoting uniform and rapid penetration of an alkali solution in reducing the alkali content of polyester fibers. The present invention relates to a penetrant that enables uniform processing without lumps.

[0002]

2. Description of the Related Art Polyester fibers are usually subjected to alkali weight reduction processing in order to finish them with a soft feel like silk. This alkali weight reduction treatment is carried out by immersing the polyester fiber in an alkali solution such as sodium hydroxide. However, in order to carry out the weight loss treatment efficiently, the surface tension is high, the wetting (penetration) is low, and the concentration is high. Since an alkali solution is required, a penetrating agent that enhances the permeability of the alkali solution to the polyester fibers has been generally used.

[0003] The penetrant used in this application is used under high-concentration strong alkaline conditions, so that it has high stability to alkalis, excellent solubility in high-concentration strong alkaline solutions, Selectively and evenly hydrolyzes the surface, does not inhibit the alkali hydrolysis reaction of polyester, has excellent surface tension lowering ability of high-concentration alkaline aqueous solution, finishes polyester fiber to soft texture, polyester What satisfy | fills all conditions, such as not reducing the intensity | strength of a system fiber, is requested | required, As such a penetrating agent, the surfactant of a phosphate ester type | system | group is used conventionally (Japanese Patent Publication No. 55-22587). ).

However, phosphate ester-based penetrants not only have insufficient solubility in aqueous alkaline solutions in a high concentration range, but also contain phosphorus, and thus have problems such as eutrophication of wastewater. However, with the growing interest in environmental issues in recent years, there has been a keen need to develop alternatives to penetrants that are safe and pollution-free for the global environment.

[0005]

SUMMARY OF THE INVENTION An object of the present invention is to provide a penetrant which satisfies all of the above-mentioned properties required for a penetrant and has higher environmental safety.

[0006]

The present inventors have conducted intensive studies to solve the above-mentioned problems, and as a result, have found that the alkyl glycoside represented by the following general formula (1) has a solubility in an alkaline solution and an alkali It has been found that the stability in a solution is high, and the above object can be achieved by using the alkyl glycoside.

That is, the present invention provides the following general formula (1)

[0008]

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[Wherein, R represents a linear or branched alkyl group having 1 to 18 carbon atoms, and X and Y are the same or different and represent -CH ₂ CH ₂ O-, -CH (CH ₃ ) CH ₂ O-
Or —CH ₂ CH (CH ₃ ) O—, G represents the same or different and represents a sugar residue having 5 or 6 carbon atoms, and n and n ′ have an average value of 0 ≦ n ≦ 10 and 0 ≦ n ′ ≦ 10, n ″ represents a number having an average value of 1 ≦ n ″ ≦ (3x + 1) or less, and x represents an average value of 1 ≦ x ≦ 10. It is an object of the present invention to provide a penetrant for alkali weight reduction processing of polyester fibers comprising at least one kind of alkyl glycosides represented by the formula (1).

In the compound of the general formula (1), as the linear or branched alkyl group having 1 to 18 carbon atoms represented by R, methyl, ethyl, n-propyl, isopropyl, n -Butyl group, isobutyl group, sec-butyl group, pentyl group, hexyl group, 2-ethylhexyl group, n-heptyl group, n-octyl group, n-nonyl group,
n-decyl group, n-undecyl group, n-dodecyl group, n
-Tetradecyl group, n-hexadecyl group, n-octadecyl group and the like, preferably a linear or branched alkyl group having 4 to 14 carbon atoms, more preferably 6 carbon atoms.
-12 straight-chain or branched alkyl groups.

N represents an average value of 0 ≦ n ≦ 10, preferably an average value of 0 ≦ n ≦ 5, more preferably 0 ≦ n ≦ 2.
Is shown. n ′ has an average value of 0 ≦ n ′ ≦ 10, preferably has an average value of 0 ≦ n ′ ≦ 5, more preferably 0 ≦ n ′ ≦
2 is shown. n ″ has an average value of 1 ≦ n ″ ≦ (3x + 1), and preferably has an average value of 1 ≦ n ″ ≦ 16. x represents an average value of 1 ≦ n ″ ≦ 10, and preferably an average value of 1 ≦ n ″
n ″ ≦ 5.

Examples of the sugar residue represented by G include sugar residues having 5 carbon atoms such as apiose, arabinose, lyxose, ribose and xylose, and glucose, galactose, mannose, fructose, altrose, and the like.
A sugar residue having 6 carbon atoms such as idose, galose, and talose is mentioned, and a preferable sugar residue is glucose. A sugar residue represented by G _x (x is 2 or more)
Examples thereof include sucrose, maltose, isomaltose, maltotriose, isomalttriose and the like.

X and Y are the same or different and each represents --CH
_{2 CH 2 O -, - CH} (CH 3) CH 2 O- or -C
H ₂ CH (CH ₃ ) O—, preferably —CH ₂ C
H ₂ O- are shown.

The compound of the present invention represented by the general formula (1) wherein n '= 0 and n is not 0 can be produced, for example, according to the method shown in the following reaction scheme (I).

Reaction scheme (I)

[0016]

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Wherein R, X, G, n and x are as defined above. However, n is not 0. The reaction involves the sugar residue G
_x and ethylene glycol monomethyl ethers (2)
Is reacted in the presence of an acid catalyst in a solvent to obtain an alkyl glycoside represented by the general formula (1a). Examples of the acid catalyst include hydrogen chloride gas, sulfuric acid, p-toluenesulfonic acid, etc., and 1 to 10 equivalents of ethylene glycol monomethyl ethers (2) per 1 mol of the sugar residue G _x , and 0.005 to 5 equivalents of the acid catalyst Use about 0.5 equivalent. N as the solvent
-Methylpyrrolidone, DMF and the like can be used, and ethylene glycol monomethyl ethers (2) itself may be used as a solvent. When ethylene glycol monomethyl ethers (2) is used as a solvent, the system becomes heterogeneous at the start of the reaction, but shifts to a homogeneous system as the reaction proceeds. The reaction time is 0.5-5 hours, and the reaction temperature is 80 ° C-1.
At 40 ° C., the reaction advantageously proceeds.

The general formula (1) of the present invention wherein n = n '= 0.
Can be produced, for example, according to the method shown in the following reaction scheme (II).

[0019]

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Wherein R, G and x are as defined above. ]
The reaction is carried out under the same conditions as in the above reaction step formula (I) except that RO-X _n (2) is replaced with ROH (3).
The compound of the present invention represented by b) is obtained.

The compound of the present invention represented by the general formula (1) in which both n 'and n are not 0 can be produced according to the method shown in the reaction scheme (III).

Reaction scheme (III)

[0023]

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Wherein R, X, Y, G, and x are the same as above, n ″ represents an average value of 0 <n ″ ≦ 10, and n and n ′ represent an average value of 0 <n ≦ 10 and 0 <n ′ ≦ 10. Reaction step The reaction is carried out by reacting 1 mol of the compound of the formula (1a) obtained in the formula (I) with 0.1 to 10 equivalents of ethylene oxide, propylene oxide or a mixture thereof in a solvent in the presence of a catalyst. Equation (1)
An alkyl glycoside represented by c) is obtained. As the solvent, ethyl acetate, N-methylpyrrolidone, DMF, water and the like can be used, but if the reaction is carried out at a temperature at which the compound of (1a) melts, the reaction can be carried out without a solvent. As the catalyst, caustic soda, caustic potash, sodium methylate, sodium ethylate and the like can be used.
The catalyst is used in an amount of 0.005 to 0.05 equivalent based on 1 mol of the compound. The reaction proceeds advantageously at a reaction time of about 0.5 to 5 hours and at a reaction temperature of about 70 to 150 ° C.

The compound of the present invention represented by the general formula (1) wherein n = 0 and n 'is not 0 can be produced according to the method shown in the reaction scheme (IV).

Reaction scheme (IV)

[0027]

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[Wherein, R, X, Y, G, and x are the same as above, n ″ represents an average value of 0 <n ″ ≦ 10, and n ′ represents an average value of 0 <n ′ ≦ 10 is shown. The reaction is RO- _Xn
The reaction is carried out under the same conditions as in the above reaction step formula (I) except that -G _x (1a) is replaced with RO-G _x (1b) to obtain a compound of the present invention represented by the formula (1d).

The polyester fibers to which the alkyl glycosides of the present invention are applied include polyester fiber materials and blended and woven materials of polyester fibers and cellulosic fiber materials. However, the cellulosic fiber material means cotton, hemp, rayon and the like, and the polyester fiber means polyethylene terephthalate, a polycondensate of dimethyl terephthalate and 1,4-cyclohexanedimethanol, dimethyl terephthalate and dimethyl isophthalate. And a polyester obtained by melt-spinning a polyester such as a mixed ester type polycondensate of ethylene glycol and ethylene glycol.

The alkali weight reduction processing of polyester fibers using the alkyl glycosides of the present invention can be carried out according to a conventional method, and specifically, for example, as follows. That is, 0.1 to 5.0% by weight of an alkyl glycoside as a penetrant is added to a 3 to 40% by weight aqueous sodium hydroxide solution, and then a cloth made of a polyester fiber is immersed in a roll batch method, a pad. It can be performed by a steam method, a batch-type hanging kneading method, or the like.

[0031]

Industrial Applicability The alkyl glycosides of the present invention have high alkali stability and solubility in an alkaline solution even though they are phosphorus-free compounds. By performing the weight reduction processing, the surface of the polyester fiber can be selectively and uniformly hydrolyzed, and the polyester fiber can be finished with a soft feel. Moreover, since it does not contain phosphorus, it has no adverse effect on the environment.

[0032]

EXAMPLES Hereinafter, the present invention will be described more specifically with reference to examples and comparative examples, but the present invention is not limited to these examples.

[0033]

Example 1 Alkali compatibility The compatibility of the alkyl glycosides of the present invention was determined using a commercially available penetrating agent for mercerizing (alcohol sulfate ester type, trade name: Neolate CM-20, manufactured by Nikka Chemical Co., Ltd.) and a commercially available penetrant. It was compared with a penetrant for alkali weight reduction processing (alcohol phosphate ester salt type, trade name: Neolate NA-30, manufactured by Nichika Chemical Co., Ltd.).

For the alkali compatibility, aqueous alkali solutions having the concentrations shown in Table 1 below were prepared using sodium hydroxide of the first grade. A predetermined amount of a penetrant was added to the solution, and the alkali compatibility was evaluated. Table 1 shows the results.

[0035] Table 1 A Le Ca Li compatibilization sodium hydroxide concentration (%) 25 30 35 penetrant concentration (%) 0.5 1.0 0.5 1.0 0.5 1.0 Sucraph AG-8 ○ ○ ○ ○ ○ ○ Sucrap AG-8 '○ ○ ○ ○ ○ ○ Sucrap AG-10 ○ ○ ○ ○ ○ △ Penetrant for mercury △ △ △ × × × Penetrant for alkali reduction processing ○ ○ ○ ○ △ △ In Table 1, Sucrap AG-8 (trade name, manufactured by Nippon Seika Co., Ltd.) contains n-octyl glucoside as a main component, and Sucrap AG-8 '(trade name, manufactured by Nippon Seika Co., Ltd.) -Ethylhexyl glucoside as a main component, and Sucrapph AG-10 (trade name, manufactured by Nippon Seika Co., Ltd.) as a main component is n-decyl glucoside.

In Table 1, ○ indicates the same state as when no penetrant was added.

△ indicates a turbid, translucent state that is separated when left for a long time.

X indicates a state in which the oily molecules are dispersed and separated when left for a short time.

From the results shown in Table 1, it was found that the penetrant of the present invention exhibited excellent compatibility even in a high concentration aqueous sodium hydroxide solution.

[0040]

Example 2 Penetration Force The penetration force of various penetrants for the same solution as in Example 1 was compared using a polyester woven fabric. Specifically, a scouring cloth made of a woven cloth (satin) of polyester fiber is used for 2.5 times.
It was cut into a size of × 2.5 cm, and a test piece was floated on the surface of each aqueous solution at 25 ° C., and the time until the test piece was completely wetted was measured. Table 2 shows the results. When no penetrant was used, 180 seconds or more was required for any of the alkaline aqueous solutions.

[0041] Table 2 and penetration force sodium hydroxide concentration (%) 25 30 35 penetrant concentration (%) 0.5 1.0 0.5 1.0 0.5 1.0 Sucraph AG-8 <1 <1 <1 <1 21 Sucrap AG-8 '<1 <1 <1 <1 <1 21 Sacrap AG-10 <1 <1 <1 2 3 2 Penetrating agent for mercerizing 5 3 9 4 18 8 Penetrating agent for alkali weight reduction processing From the results shown in Table 2, it was revealed that the penetrant of the present invention significantly improved the wetting of polyester fibers.

[0042]

Example 3 Surface tension The surface tension of the same solution as in Example 1 was measured at 25 ° C. using a Genuine surface tensiometer. Each measured value was converted into a specific surface tension using the following formula: specific surface tension = surface tension of each solution / surface tension of water. The results are shown in Table 3 below.

Table 3Specific surface tension Sodium hydroxide concentration (%) 25 30 35 Penetrant concentration (%) 0.5 1.0 0.5 1.0 0.5 1.0 Sucrap AG-8 0.422 0.390 0.428 0.420 0.453 0.450 Sucrap AG-8 '0.483 0.472 0.492 0.491 0.502 0.491 Sucrap AG-10 0.382 0.380 0.400 0.402 0.430 0.421 Penetrant for mercerizing 0.600 0.587 0.619 0.608 0.620 0.618 Penetrant for alkali reduction processing 0.448 0.439 0.455 0.483 0.470 Without penetrant 1.17 1.17 1.20 1.20 1.30 1.30 From the results in Table 3, the penetrant of the present invention is the same as the conventional penetrant.
Has the effect of lowering the specific surface tension of polyester fiber
It turned out to be.

[0044]

Example 4 a) Pat roll batch test Polyester satin was immersed in a predetermined solution containing 0.5% of various penetrants at room temperature, and a pickup rate of 8 was obtained with a mangle.
A 5% squeezing was performed. The squeezed cloth was put in a polyvinyl bag, left at 40 ° C. ± 2 ° C. for 15 hours, washed with water, air-dried, and the weight of the polyester satin was measured to calculate the weight loss rate. Was. The results are shown in Table 4 below. Table 4 Weight loss rate Sodium hydroxide concentration (%) 25 30 35 Sucrap AG-8 23.0 23.5 24.0 Sucrap AG-8 '22.6 23.1 23.1 Sucrap AG-10 21.3 23 6.6 23.9 Penetrant for mercury 11.8 12.3 13.2 Penetrant for alkali weight loss processing 21.5 23.4 23.8 No penetrant 21.8 23.3 23.7 From the results in Table 4 It has been clarified that the penetrant of the present invention has a weight-reducing effect on polyester fibers equal to or higher than that of the conventional penetrant.

B) Effect on Weight Loss Reaction Polyester satin was immersed in a 30% aqueous sodium hydroxide solution (40 ° C.) containing 0.5% of Sucrap AG-8, and a pickup rate of 85% was squeezed with a mangle. Put the squeezed cloth in a polyvinyl bag, 40 ℃ ± 2 ℃
, And the weight loss rate at each time was measured. The results are shown in FIG.

Incidentally, in FIG. 1, ○ indicates Sucrap AG.
-8 shows the weight loss rate when -8 is added, and ● shows the weight loss rate when no penetrant is added.

From the results shown in FIG. 1, it was confirmed that the penetrant of the present invention did not inhibit the weight loss reaction unlike the conventional penetrant for mercerizing.

C) Pad-steam method Polyester satin is immersed in a predetermined solution containing 0.5% of various penetrants at normal temperature, and a pickup rate of 8 using a mangle.
A 5% squeezing was performed. This was put on a tenter, steamed at 100 ° C. for 20 minutes, washed with water and dried, and the weight loss of polyester satin was measured. The results are shown in Table 4 below.

Table 4 Weight loss rate Sodium hydroxide concentration (%) 25 30 35 Sucrap AG-8 20.8 21.3 22.1 Sucrap AG-8 '20.7 20.9 22.0 Sucrap AG-10 20 .2 20.8 21.2 Mercerizing penetrant 16.3 17.2 18.8 Alkaline weight loss processing penetrant 19.8 21.1 21.9 No penetrant 19.5 19.8 20.2 Table 5 From the results, it has been clarified that the penetrant of the present invention has a polyester fiber weight reduction action equal to or higher than that of the conventional penetrant.

[Brief description of the drawings]

FIG. 1 is a graph showing the effect of weight loss on Sucrap AG-8 on polyester satin.

──────────────────────────────────────────────────続 き Continuing on the front page (72) Inventor Masakazu Okumura 5-1-1, Umei, Takasago City Nippon Seika Co., Ltd. (58) Field surveyed (Int. Cl. ⁷ , DB name) D06M 13/00 -13/493 D06M 11/38

Claims (1)

(57) [Claims] 1. A compound represented by the following general formula (1): RO-X _n -G _x- (Y _{n ′} H) _{n ″} (1) X and Y are the same or different and represent a branched alkyl group;
_{H 2 CH 2 O -, -} CH (CH 3) CH 2 O- or -CH
₂ CH (CH ₃ ) O—, G represents the same or different and represents a sugar residue having 5 or 6 carbon atoms, and n and n ′ represent an average value of 0 ≦ n ≦ 10 and 0 ≦ n ′ ≦ 10. And n ″
Indicates a number whose average value is 1 ≦ n ″ ≦ (3x + 1) or less,
x indicates an average value of 1 ≦ x ≦ 10. ] The penetrant for alkali weight reduction processing of the polyester fiber which consists of at least 1 type of alkyl glycoside represented by these.