JPH0649440A - Antistatic agent composition - Google Patents

Abstract

PURPOSE:To obtain an antistatic agent composition providing synthetic fiber and synthetic resins with excellent antistatic properties with a small amount, comprising an amphoteric surfactant having a specific structure and its salt. CONSTITUTION:The composition comprises an amphoteric surfactant of formula I (R is 8-24C alkyl or alkenyl; R' is ethylene and/or propylene; n is 1-50; R1 and R2 are <=5C alkyl) and its monovalent or bivalent metal salt. The composition is preferably obtained by adding ethylene oxide and/or propylene oxide to a 8-24C alcohol to give an adduct of the formula RO(R'O)nH, reacting the adduct with a thionyl halide, reacting a formed compound of formula II (X is halogen) with a dialkyklamine in the presence of an alkali and then reacting a prepared compound of formula III with a monohalogenoacetate of formula IV (M is monovalent alkali metal).

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to antistatic agents such as synthetic fibers and synthetic resins.

[0002]

2. Description of the Related Art Conventionally, synthetic fibers, synthetic resin products, etc. are prone to electrification, which has been a big problem. Various antistatic agents have been developed to solve this problem, but the effects are not always sufficient. Further, high performance antistatic agents have been demanded.

[0003]

In view of the current state of such antistatic agents, the inventors of the present invention have earnestly studied antistatic agents of higher performance, and arrived at the present invention.

[0004]

That is, the present invention provides a novel antistatic composition.

(Wherein R is an alkyl group having 8 to 24 carbon atoms, an alkenyl group, R'is ethylene and / or propylene, n is an integer of 1 to 50, R ₁ and R ₂ are alkyl groups having 5 or less carbon atoms. The present invention proposes a novel amphoteric surfactant which is a betaine compound represented by the formula (1) and a monovalent or divalent metal salt thereof.

The antistatic agent composition of the present invention is disclosed in JP-A-60-
It can be synthesized by the following reaction disclosed in 89458. (1) ROH + n (R'O) → RO (R'O) nH (2) RO (R'O) nH + SOX ₂ → RO (R'O) _n-1 R'X + SO ₂ + HX

[0006]

[0007] →

Embedded image (wherein R is an alkyl group having 8 to 24 carbon atoms, an alkenyl group, R ′ is ethylene and / or propylene, and n is 1 to 5).
An integer of 0, R ₁ and R ₂ are alkyl groups having 5 or less carbon atoms, X is a halogen atom, and M is a monovalent alkali metal. )

The reaction (1) is a higher alcohol having 8 to 24 carbon atoms, for example, octanol, decanol, lauryl alcohol, cetyl alcohol, stearyl alcohol, behenyl alcohol, oleyl alcohol, 11 to 1 carbon atoms.
1 to 5.0 of ethylene oxide and / or propylene oxide is added to 1 mol of a higher alcohol such as an oxo-method mixed alcohol of 5, a secondary alcohol having 12 carbon atoms, and tridecyl alcohol by a known method. From the viewpoint of properties and usefulness, lauryl alcohol, myristyl alcohol, oleyl alcohol, tridecyl alcohol, and 1 mol of the oxo-method mixed alcohol having 11 to 15 carbon atoms and 2 to 10 mol of ethylene oxide added are preferable.

In the reaction (2), 1 mol of the higher alcohol alkylene oxide adduct thus obtained is added with thionyl halide, preferably 1 mol of thionyl chloride at 40 to 100 ° C.
React with. At this time, it is desirable to use dimethylformamide as a catalyst in an amount of about 1% and to distill it off.

In the reaction (3), 1 mol of the terminal halide obtained in the reaction (2) is reacted with a dialkylamine such as dimethylamine, diethylamine, dipropylamine, dibutylamine, preferably dimethylamine, and the alkali is heated at 100 ° C. or lower. , An aqueous solution of 1 mol of caustic potash and caustic soda is added.

The reaction (4) is carried out by adding 1 mol of the thus obtained tertiary amine compound to a monohalogen acetate at 50 to 100 ° C.
Preferably, 1 mol of sodium monochloroacetate is added as an aqueous solution and reacted. At this time, 1 mol of alkali, for example, caustic soda, caustic potash, magnesium hydroxide, zinc hydroxide, calcium hydroxide or the like can be added to obtain the alkali metal salt of the product.

The antistatic agent of the present invention thus obtained exhibits a superior antistatic effect on synthetic fibers, synthetic resins and the like in a small amount, and shows a superior antistatic effect on synthetic fibers and wool in a small amount. It is used as a component of synthetic fiber, wool spinning, spinning oil, and as an antistatic agent for kneading or coating synthetic resin as a finishing agent for final products.

The present invention will be described below with reference to examples.

【Example】

Examples 1 to 3 450 g of poly (6) oxyethylene lauryl ether (1 mol) obtained by adding 6 mol of ethylene oxide to 1 mol of lauryl alcohol was placed in a 4-necked Korben, 5 g of dimethylformamide was added, and the temperature was raised to 70 ° C. After that, 119 g of thionyl chloride (1 mol) was gradually added dropwise over 1 hour, and the reaction was continued for 6 hours. Then 1
The temperature was raised to 20 ° C., N ₂ gas was introduced, dedimethylformamide was carried out for 2 hours, and a pale yellow liquid OHV at room temperature:
468.5 g of lauryloxypoly (5) ethyleneoxyethyl chloride having a content of 0.2 and a Cl content of 7.5% was obtained. Then, 46 mol of 1 mol of lauryloxypoly (5) ethyleneoxyethyl chloride was placed in an autoclave, 45 g of 1 mol of dimethylamine was added, and the temperature was raised to 140 ° C. to react for 4 hours. Then, the mixture was cooled and transferred to a four-necked Kolben, and 100 g of a 40% aqueous solution of caustic soda was added at 60 ° C., then 241 g of a 40% aqueous solution of sodium monochloroacetate was added, and the mixture was reacted at 80 ° C. for 6 hours. Then, N ₂ gas was introduced, dehydration was carried out at 105 ° C., and filtration was carried out to obtain 528 g of a betaine compound having a pale yellow liquid at room temperature, water content of 0.1%, N: 2.60% and pH (1%) of 6.7. It was This product is subjected to the following test as Example 1 together with Examples 2 and 3 below.

Next, 528 g of this product was dissolved in 350 g of a 10% sodium hydroxide solution and 693 g of water to obtain Example 2 having a solid content of 35% and a pH of 8.4 of 1%. Further, 80 g of an aqueous dispersion of 40 g of magnesium hydroxide was added to 528 g of this product, kneaded well, and then dehydrated to obtain Example 3.

[0015]

Examples 4 to 6 Poly (2) oxypropylene poly (5) oxyethylene myristyl ether 1 mol 544 g obtained by adding 2 mol of propylene oxide and 5 mol of ethylene oxide to 1 mol of myristyl alcohol were placed in a four-necked Korben, and dimethylform was prepared. Add 6g of amide, 70 ℃
Then, 1 mol of thionyl chloride (119 g) was gradually added to 1
The solution was added dropwise over a period of time, and the reaction was continued for 6 hours. After that, the temperature was raised to 120 ° C., N ₂ gas was introduced, and dedimethylformamide was carried out for 2 hours.
V: 0.1, myristyloxypoly (2) with Cl content of 6.3%
562.5 g of propyleneoxy poly (4) ethyleneoxyethyl chloride was obtained. Next, 562.5 g of 1 mol of the obtained terminal chlorinated product was placed in an autoclave,
45 g of 1 mol of dimethylamine was added, the temperature was raised to 140 ° C., and the reaction was carried out for 4 hours. After cooling, transfer to a four-necked Kolben, add 100 g of 40% aqueous solution of caustic soda at 60 ° C,
Next, 241 g of a 50% aqueous solution of sodium monochloroacetate was added, and the mixture was reacted at 80 ° C. for 6 hours. After that, N ₂ gas was introduced, the temperature was raised to 105 ° C., dehydration, filtration, and a pale yellow liquid at room temperature, water content 0.05%, Cl: 0.01%, N: 2.22
%, PH (1%): 6.9 g of betaine compound (6.9 g) were obtained. This product is subjected to the test described below as Example 4.

Next, 63 g of this product was dissolved in 52 g of 10% aqueous potassium hydroxide solution and 73 g of water to obtain Example 5 having a solid content of 35%. This product is subjected to the test described below. Next, 63 g of this product and 8 g of barium hydroxide were added, kneaded well, and then dehydrated to obtain Example 6. This product is subjected to the test described below.

[0017]

[Embodiments 7 and 8] Similar to Embodiments 1 and 3, Embodiment 7,
8 was obtained as in Table 1. This product is subjected to the test described below.

Performance Test 1 After degreasing Toray polyester taffeta with carbon tetrachloride,
It was dipped in a 0.5% solid content solution of each of Examples 1, 2, 4, 5, 7, and 8 at 40 ° C. for 1 minute, then squeezed to 100% and air dried. Next, these treated cloths were treated at 20 ° C. and 60% R.C. H. The sample was allowed to stand in a constant temperature and humidity chamber for 48 hours, and the surface resistivity was measured with a teraohm meter model VE-30 manufactured by Kawaguchi Electric Co., Ltd., and the results shown in Table 2 were obtained.

[0019]

Performance test 2 Polyvinyl chloride powder 100 g, DOP 45 g,
2 g of the cadparly stabilizer and 2 g of the sample obtained in Example 3 or 6 were mixed and kneaded with a baby roll at 180 ° C. for 10 minutes to form a film. Then these films
0 ° C., 60% R. H. After leaving it in the constant temperature and humidity chamber for 48 hours, it is made by Kawaguchi Electric Co., Ltd., Tera ohm meter model VE-30
The surface resistivity was measured with and the results shown in Table 3 were obtained.

[0021]

[0022]

As is apparent from the examples, it is clear that the amphoteric surfactant of the present invention imparts excellent antistatic performance to synthetic fibers and synthetic resins.

Claims (1)

[Claims] 1. The following general formula: (However, R is an alkyl group having 8 to 24 carbon atoms, an alkenyl group, R'is ethylene and / or propylene, and n is 1 to 5
An integer of 0, R ₁ and R ₂ are alkyl groups having 5 or less carbon atoms. ) An amphoteric surfactant and an antistatic agent composition comprising a monovalent or divalent metal salt thereof.