JPH0617091A - Sulfobetaine ampholytic surfactant - Google Patents

Abstract

PURPOSE:To obtain a sulfobetaine ampholytic surfactant whose hydrophilicity level can be adjusted, by forming a compound having a specified molecular structure. CONSTITUTION:The surfactant is represented by the formula, wherein R is 8-24C alkyl or alkenyl; R' is an ethylene and/or propylene group; n is an integer of 1 to 50; and R'' is 5C or lower alkyl. It has good solubility in an alcohol and in water in a wide pH range 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 can be widely used for detergents and the like.

[0002]

2. Description of the Related Art Recently, amphoteric surfactants have surface activity in a wide pH range and are compatible with any type of anionic, cationic, and nonionic surfactants, and thus are used in various industrial fields. It has come to be widely used.

[0003]

However, in the conventional amphoteric surfactant, the degree of hydrophilicity is determined by the type of the alkyl group, and like the nonionic surfactant, the hydrophilicity depends on the number of added moles of ethylene oxide. I couldn't adjust the degree.

[Means for Solving the Problems]

The present inventors have arrived at the present invention as a result of earnestly researching novel amphoteric surfactants, paying attention to the usefulness and improvement points of such amphoteric surfactants. That is,
The present invention has the general formula

Embedded image (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, and R "is an alkyl group having 5 or less carbon atoms.) Is a novel sulfobetaine-type 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 → R (OR ') X + S
O ₂ + HX (3) R (OR ') X + (R ") ₂ NH + MOH → R (OR') N (R") ₂ + MX + H ₂ O (4) R (OR ') N (R ") ₂ + XCH ₂ CH (OH) CH ₂ S
O ₃ M →

Embedded image (wherein R is an alkyl group having 8 to 24 carbon atoms, an alkenyl group, R ′ is an ethylene or propylene group, 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 such as octanol, decanol, lauryl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol, behenyl alcohol, oleyl alcohol, oxo process mixed alcohol having 11 to 15 carbons, carbon. 1 to 50 of ethylene oxide or / and propylene oxide is added to 1 mol of a secondary alcohol of the formula 12 or a higher alcohol such as tridecyl alcohol by a known method.
In terms of economic efficiency and usefulness, lauryl alcohol, myristyl alcohol, and oleyl alcohol are prepared by adding 2 to 10 moles of ethylene oxide to 1 mole of the oxo-method mixed alcohol having 11 to 15 carbon atoms. 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 halide obtained in the reaction (2) is dialkylamine such as dimethylamine, diethylamine, dipropylamine, dibutylamine, preferably 1 mol or more of dimethylamine is caustic soda,
It can be obtained by reacting at 100 to 180 ° C. in the presence of 1 mol or more of potassium hydroxide under normal pressure or under pressure, preferably under pressure.

The reaction (4) is carried out by adding 1 mol of sodium monohalogen hydroxypropyl sulfonate as an aqueous solution to 1 mol of the tertiary amine compound thus obtained at 50 to 100 ° C. At this time, it is also possible to add 1 mol of alkali, for example, caustic soda to obtain the carboxylic acid sodium salt of this product, and in this case the reactivity is higher.

The amphoteric surfactant of the present invention obtained in the reaction (4) is optionally dehydrated and filtered, or a purified product can be obtained by filtering with a large amount of isopropanol or the like, followed by dehydration and solvent removal. The amphoteric surfactant of the present invention has an IR spectrum of 3300 and 2 when the purified product is obtained.
Absorption is observed in 930, 2870, 1110, 1050 Kaiser. The amphoteric surfactant of the present invention is used as a detergent, a foaming agent, an AE agent, etc., and the hydrophilicity can be adjusted according to the purpose by changing the number of moles of alkylene oxide added as a starting material. .

[0011]

EXAMPLES Examples of the present invention will be shown below.

Example 1 450 g of 1 mol of poly (6) oxyethylenelauryl ether obtained by adding 6 mol of ethylene oxide to 1 mol of lauryl alcohol was placed in a four-necked Korben, 5 g of dimethylformamide was added, and the temperature was raised to 70 ° C. Thionyl chloride (1 mol, 119 g) was gradually added dropwise over 1 hour, 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 to obtain a pale yellow liquid at room temperature, OHV: 0.2, C
There were obtained 468.5 g of lauryl poly (6) oxyethylene chloride with 1 min: 7.5%. Next, 468.5 g of lauryl poly (6) oxyethylene chloride was placed in an autoclave, and 90 g of dimethylamine (2 mol) was added. % Aqueous solution 100 g,
Further, the mixture was reacted at 150 ° C. for 5 hours and then cooled, and N ₂ gas was introduced at 90 ° C. to distill excess methylamine.
Then, 766 g of 25% sodium monochlorohydroxypropyl sulfonate was added and reacted at 80 ° C. for 30 hours. Thereafter, 1 kg of isopropyl alcohol was added and filtered, and then N ₂ gas was introduced to dehydrate and desolvate at 80 to 105 ° C., and a pale yellow liquid at normal temperature, water content: 0.1
%, Cl: 0.02%, N: 2.32%, S: 5.32
%, PH (1%) 6.1 amphoteric surfactant 595 g was obtained. 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, and 1 mol of poly (2) oxypropylene poly (5) oxyethylene myristyl ether 544 g was placed in a four-necked corben and 6 g of dimethylformamide was used. After the temperature was raised to 70 ° C., 1 mol of thionyl chloride (119 g) was gradually added dropwise over 1 hour, and the reaction was further continued for 6 hours. Then 120
The temperature was raised to ℃, N ₂ gas was introduced, and dedimethylformamide was carried out for 2 hours. A pale yellow liquid at room temperature, OHV: 0.0
562.5 g of myristyl poly (2) oxypropylene poly (5) oxyethylene chloride having a Cl content of 6.3% was obtained. Then, 1 mol 56 of the obtained terminal chlorinated product
Take 2.5 into the autoclave and add 1 mole 4 of dimethylamine.
5 g was added and the temperature was raised to 140 ° C. to react for 4 hours. Then, cool, transfer to a four-neck Kolben, and add caustic soda 40 at 60 ℃.
% Aqueous solution 100 g, and then 25% sodium monochlorohydroxypropylsulfonate aqueous solution 766 g was added, and the reaction was carried out at 80 ° C. for 24 hours. After that, N ₂ gas was introduced, the temperature was raised to 105 ° C., dehydration was performed, and filtration was carried out at room temperature to give a pale yellow liquid, moisture 0.05%, Cl 0.01%, N 1.99%,
S: 4.54%, pH (1%) 6.0 amphoteric surfactant 69
9 g was obtained. This product is subjected to the test described below.

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

[0014]

[Table 1]

[0015] The solubility shows the state at 20 ° C. by mixing 1 g of the amphoteric surfactant of Examples 1 to 18 and the test liquid: 99 gr. Unit of surface tension: dyne / cm

[0016]

As shown in Table 2, the amphoteric surfactant of the present invention is well soluble in alcohol and water in a wide pH range and exhibits surface tension lowering ability.

Claims (1)

[Claims] 1. A sulfobetaine-type 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 5
0 is an integer, R "represents an alkyl group having 5 or less carbon atoms)