JPH0617090A - Ampholytic surfactant - Google Patents

Abstract

PURPOSE:To obtain a new ampholytic surfactant whose lipophilicity and hydrophilicity can be adjusted in accordance with purposes, by forming a constitution having both an alkylene oxide group and a betaine group as the hydrophilic groups. CONSTITUTION:An ampholytic surfactant represented by the formula, wherein R is 8-24C alkyl or alkenyl; R' is an ethylene and/or propylene group; n is 1 to 20; and R'' is 5C or lower alkyl. It has good solubility in water, whether acidic, neutral or alkaline, and in an alcohol and exhibits an excellent ability to reduce surface tension.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel amphoteric surfactant, which is widely used for detergents and the like. Recently, amphoteric surfactants have surface activity in a wide range of pH, and are compatible with any type of anionic, cationic, and nonionic surfactants, and thus have been widely used in various industrial fields. There is. The present inventors have arrived at the present invention as a result of earnestly researching novel amphoteric surfactants while paying attention to the usefulness of such amphoteric surfactants.

[0002]

2. Description of the Related Art Conventionally, it has been difficult to adjust the lipophilicity and hydrophilicity of an amphoteric surfactant according to the purpose, and the degree thereof is determined by the alkyl group.

[0003]

The present invention has an alkylene oxide group and a betaine group as hydrophilic groups,
The lipophilicity and hydrophilicity can be adjusted according to the purpose.

[0004]

The present invention has the general formula

(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 20, and R "is an alkyl group having 5 or less carbon atoms. ) Is proposed as a new amphoteric surfactant.

The amphoteric surfactant of the present invention is synthesized by the following reaction. (1) ROH + n (R'O) → RO (R'O) nH (2) RO (R'O) nH + SOX ₂ →

[Chemical 2] + SO ₂ + HCl (3) 2

[Chemical formula 2] + R "NH + 2MOH →

[Chemical 3] + 2MX + 2H ₂ O (4)

[Chemical Formula 3] + XCH ₂ COOM →

Embedded image (provided that R is an alkyl or alkenyl group having 8 to 24 carbon atoms, R ′ is ethylene and / or propylene, and n is 1 to 5)
(An integer of 0, R "is an alkyl group 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, myristyl alcohol, cetyl alcohol, stearyl alcohol, behenyl alcohol, oleyl alcohol, oxo process mixed alcohol having 11 to 15 carbon atoms,
1 to 5 of ethylene oxide or / and propylene oxide is added to 1 mol of a higher alcohol such as a secondary alcohol having 12 carbon atoms or tridecyl alcohol by a known method.
Although 0 mol is added, 2 to 10 mol of ethylene oxide is added to 1 mol of lauryl alcohol, myristyl alcohol, oleyl alcohol, and an oxo-method mixed alcohol having 11 to 15 carbon atoms from the viewpoint of economy and usefulness. Those are preferable. Also, the adduct of propylene oxide alone is not useful.

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.
Alternatively, hydrochloric acid gas may be reacted at 100 to 150 ° C.

In the reaction (3), 1 mol of the terminal halogenated product obtained in the reaction (2) is added to a monoalkylamine such as methylamine,
Propylamine, butylamine, preferably methylamine in an amount of 1 mol or more in the presence of caustic soda or caustic potash of 1 mol or more at atmospheric pressure or under pressure, preferably 100 to 180 under pressure.
Obtained by reacting at ℃.

In the reaction (4), 1 mol of the thus obtained tertiary amine compound is added with 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, it is also possible to add 1 mol of alkali, for example, caustic soda, to obtain the alkali metal salt of this product. The amphoteric surfactant of the present invention obtained in the reaction (4) may be purified by dehydration filtration if necessary.

The amphoteric surfactants of the present invention have IR absorption spectra of 2930 and 287 when obtaining their purified products.
0, 1640, 1600, 1470, 1270, 111
Absorption is observed at 0 Kaiser. The amphoteric surfactant of the present invention is used for detergents, foaming agents, AE agents and the like.

[0011]

EXAMPLES Examples of the present invention will be shown below.

Example 1 1 mol of poly (6) cyethylenelauryl ether obtained by adding 6 mol of ethylene oxide to 1 mol of lauryl alcohol, 450 g was placed in a four-necked Korben, 5 g of dimethylformamide was added, and the temperature was raised to 70 ° C. Then, 119 g of thionyl chloride (1 mol) was gradually added dropwise over 1 hour, and the reaction was continued for 6 hours. Then 120 ° C
The temperature was raised to _2, N ₂ gas was introduced, dedimethylformamide was carried out for 2 hours, and a pale yellow liquid at room temperature, OHV: 0.0
2, 468.5 g of 1 mol of lauryloxypoly (5) ethyleneoxyethyl chloride having a Cl content of 7.5% was obtained. Next, 46 mol of 1 mol of lauryloxypoly (5) ethyleneoxyethyl chloride was placed in an autoclave, 0.6 mol of methylamine and 18.6 g of methylamine were added, the temperature was raised to 140 ° C. and the reaction was carried out for 4 hours, followed by cooling. Move to mouth Kolben 6
At 0 ° C, add 50 g of 40% aqueous solution of caustic soda, and add 15 more
After reacting at 0 ° C for 5 hours, the mixture was cooled and excess methylamine was distilled at 90 ° C by introducing N ₂ gas. Next, add 121 g of a 50% aqueous solution of sodium monochloroacetate,
The reaction was allowed to proceed at 0 ° C for 6 hours. After that, N ₂ gas was introduced, dehydration filtration was performed at 105 ° C., and a pale yellow liquid was obtained at room temperature.
0.1%, Cl: 0.02%, N: 1.47%, pH (1
%) 6.6 amphoteric surfactant 468 g. This product is subjected to the test described below.

[0012]

Example 2 1 mol of myristyl alcohol, 2 mol of propylene oxide and 5 mol of ethylene oxide were added to poly (2) oxypropylene polyoxy (5) ethylene myristyl ether 1 mol, 544 g was taken in a four-necked corben, and dimethylform was prepared. After 6 g of amide was added and the temperature was raised to 70 ° C., 119 g of 1 mol of thionyl chloride 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 at room temperature, OHV:
Myristyloxypoly (2) propylene poly (4) ethyleneoxyethyl chloride 56 having 0.1 and a Cl content of 6.3% 56
2.5 g was obtained. Then, the above-obtained terminal chlorinated compound 1
Mole 562.5 g was put in an autoclave, methylamine 0.5 mol 15.5 g was added, the temperature was raised to 140 ° C., reacted for 4 hours, cooled, transferred to a four-necked Korben, and 50 g of caustic soda 40% aqueous solution was added at 60 ° C. Next, 122 gr 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., dehydrated, filtered, and a pale yellow liquid at room temperature, water content 0.05%, C
Thus, 554 g of a betaine compound having a l: 0.01%, N: 1.22% and pH (1%) of 6.8 was obtained. This product is subjected to the test described below.

[0013]

Examples 3 to 18 Table 1 is the same as in Examples 1 and 2.
Examples 3 to 15 were synthesized as described above. These will be used in the tests described below. Table 2 shows the solubility and surface activity of the compounds of Examples 1-18. As shown in Table 2, all the compounds of Examples 1 to 18 have excellent surface activity.

[0014]

[Table 1]

[0015]

Washing test 10 g of a cotton cloth to which 2% beef tallow was adhered was placed in a 500 cc beaker, and each of the compounds of Examples 1, 3, 7, and 16 was added to 0.10.
5 Aqueous solution (300 cc) was added, and the mixture was kept at 40 ° C. and stirred and washed for 5 minutes with a stirring rod. After air-drying each wash cloth, the beef tallow of the wash cloth was measured by the ether extraction method.
21%, 0.11% and 0.24% showed good cleaning effect.

[0017]

As shown in the examples, the amphoteric surfactant according to the present invention is well soluble in water and alcohol regardless of acidity, neutrality or alkalinity, and exhibits an excellent surface tension lowering ability.

Claims (1)

[Claims] 1. A novel amphoteric surfactant represented by the following general formula. [Chemical 1] (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 2
(An integer of 0, R "represents an alkyl group having 5 or less carbon atoms)