JPH0460102B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention relates to a process for preparing amphoteric surfactant betaine compounds. Recently, betaine compounds, which belong to amphoteric surfactants, have surface activity over a wide pH range and are compatible with all types of surfactants, anionic, cationic, and nonionic, so they are widely used in various industrial fields. It has come to be used. The present inventor focused on the usefulness of such amphoteric surfactants and conducted intensive research on new amphoteric surfactants, and as a result arrived at the present invention. However, R is an alkyl or alkenyl group having 8 to 24 carbon atoms, R' is ethylene and/or propylene,
We propose a betaine compound represented by the following formula (n is an integer from 1 to 50, R ₁ and R ₂ are alkyl having 5 or less carbon atoms) as a new amphoteric surfactant. The betaine compound of the present invention is synthesized by the following reaction. (1) ROHH+n(R ³ )→RO(R′O) _oH (2) RO(R′O)nH+SOX ₂ →RO(R′O) _o-1 R′X+
SO ₂ +HCl (R is an alkyl or alkenyl group having 8 to 24 carbon atoms, R' is ethylene and/or propylene, n is an integer of 1 to 50, R ₁ R ₂ is an alkyl group having 5 or less carbon atoms, and X is a halogen atom. , M is a monovalent alkali metal.) Reaction (1) is a higher alcohol having from 24 carbon atoms, such as octanol, decanol, lauryl alcohol, myristyl alcohol, cetyl alcohol,
Higher alcohols such as stearyl alcohol, behenyl alcohol, oleyl alcohol, oxo mixed alcohol with 11 to 15 carbon atoms, secondary alcohol with 12 carbon atoms, tridecyl alcohol, etc.1
ethylene oxide or/and in a known manner.
It adds about 1 to 50 moles of propylene oxide, but from the viewpoint of economy and usefulness, lauryl alcohol, myristyl alcohol, oleyl alcohol, tridecyl alcohol, carbon number
It is preferable to add 2 to 10 moles of ethylene oxide to 1 mole of oxo mixed alcohol of 11 to 15. Also, adducts of only propylene oxide have no utility. Reaction (2) is to add thionyl halide, preferably thionyl chloride, to 1 mol of the higher alcohol alkylene oxide adduct thus obtained at 40 to 100°C.
React at At this time, it is preferable to use dimethyl formamide as a catalyst in an amount of about 1% of the total amount, and to perform post-distillation. In reaction (3), 1 mole of the unterminated halide obtained in reaction (2) is added with a dialkylamine such as dimethylamine, diethylamine, dipropylamine,
1 mole of an alkylamine such as dibutylamine, preferably dimethylamine, is reacted at 80 to 180° C. under normal pressure or under pressure, and then,
Add an alkali such as caustic potash or a 1 mol aqueous solution of caustic soda at a temperature below 100°C. Reaction (4) is the thus obtained tertiary amine compound 1
A monohalogen acetate, preferably 1 mole of monochlorosodium acetate, is added to the mol at 50 to 100°C as an aqueous solution and reacted. At this time, it is also possible to add 1 mol of alkali, such as caustic soda, to obtain the alkali metal salt of this product. The surfactant betaine compound of the present invention obtained in reaction (4) can be optionally dehydrated to obtain a purified product. When the surfactant betaine compound of the present invention is purified, its IR spectrum shows 2930, 2870,
Absorption is observed at 1640, 1600, 1470, 1270, and 1110 (cm ^- ). The compound of the present invention is an excellent amphoteric surfactant and is used as a detergent penetrant, foaming agent, wetting agent, AE agent, etc. Next, examples of the present invention will be shown. Example 1 450 g of 1 mole of poly(6)oxyethylene lauryl ether with 6 moles of ethyl oxide attached to 1 mole of lauryl alcohol was placed in a four-necked colben, 5 g of dimethyl formamide was added, and the temperature was raised to 70°C. 1 mole of thionyl chloride (119 g) was gradually added dropwise over 1 hour, and the reaction was continued for a further 6 hours. then 120
The temperature was raised to ℃, N ₂ gas was introduced, and dimethylformamide was removed for 2 hours, resulting in a pale yellow liquid at room temperature.
468.5 g of lauryloxypoly(5) ethyleneoxyethyl chloride with OHV: 0.2 and Cl content of 7.5% was obtained.
Next, 1 mol (468.5 g) of lauryloxypoly(5) ethyleneoxyethyl chloride was placed in an autoclave, 1 mol (45 g) of dimethylamine was added, the temperature was raised to 140°C, the mixture was reacted for 4 hours, and then cooled and transferred to a four-necked Kolben at 60°C. Add 100g of 40% caustic soda aqueous solution,
Next, 241 g of a 50% aqueous solution of monochlorosodium acetate was added and reacted at 0°C for 6 hours. After that, N ₂ gas was introduced and dehydrated at 105℃, which turned into a pale yellow liquid at room temperature, moisture 0.1%, Cl: 0.03%, N: 2.60%, PH.
(1%) 528 g of a betaine compound of 6.7 was obtained. This product will be subjected to the tests described below. Example 2 1 mole of poly(2) oxypropylene poly(5) oxyethylene myristyl ether (544 g of poly(2) oxypropylene poly(5) oxyethylene myristyl ether added to 1 mole of myristyl alcohol, 2 moles of propylene oxide and 5 moles of ethylene oxide) was placed in a four-necked colben, and 6 g of dimethyl formamide was added thereto. addition
After raising the temperature to 70°C, 1 mole of thionyl chloride (119 g) was gradually added dropwise over a period of 1 hour, and the reaction was continued for a further 6 hours. After that, the temperature was kept at 120℃, N ₂ gas was introduced, and dimethylformamide was removed for 2 hours. Myristyloxypoly(2)propyleneoxypoly(4) became a pale yellow liquid at room temperature, OHV: 0.1, Cl content 6.3%. Ethyleneoxyethyl chloride 562.5 was obtained. Next, 1 mol 562.5 g of the obtained unterminated chloride was placed in an autoclave, and 1 mol 45 g of dimethylamine was added thereto.
After raising the temperature to ℃ and reacting for 4 hours, it was cooled and transferred to a four-necked kolben, and 100 g of a 40% aqueous solution of caustic soda was added at 60℃, followed by a 50% aqueous solution of sodium monochloroacetate.
241g was added and the reaction was continued at 80°C for 6 hours. after that
Introducing _N2 gas, heating to 105℃, dehydration, filtering, pale yellow liquid at room temperature moisture 0.05%, Cl: 0.01%, N: 2.22
% and PH (1%) of 6.9, 614 g of betainate was obtained.
This product will be subjected to the tests described below. Examples 3 to 18 Examples 3 to 15 were synthesized in the same manner as in Examples 1 and 2 as shown in Table 1. These will be subjected to the tests described later. Table 2 also shows the solubility and surface activity of the compounds of Examples 1 to 18. As shown in Table 2, the compounds of Examples 1 to 18 all have excellent surface activity.

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Claims (1)

[Claims] 1. The following general formula (However, R is an alkyl or alkenyl group having 8 to 24 carbon atoms, R' is ethylene and/or propylene, n is an integer of 1 to 50, and R ₁ and R ₂ are alkyl groups having 5 or less carbon atoms.) Amphoteric surfactant betaine compounds represented. 2. 1 mole of polyoxyalkylene alkyl ether or polyoxyalkylene alkenyl ether prepared by adding 1 to 50 moles of ethylene oxide and/or propylene oxide to 1 mole of higher alcohol having 8 to 24 carbon atoms is reacted with 1 mole of thionyl halide. Tertiary amine compound 1 obtained by substituting the terminal -OH group with -X (X is halogen), then reacting the obtained unterminated halide with a dialkylamine having 5 or less carbon atoms, and then dehalogenating with an alkali. 1. A method for producing an amphoteric surface-active betaine compound, which comprises reacting 1 mol of a monohalogen acetate with 1 mol of a monohalogen acetate. 3 In the general formula, R is dodecyl, tridecyl, tetradecyl, oleyl, or a mixed alkyl group having 11 to 15 carbon atoms, R' is ethylene, n is 2 to 10, and R ₁ and R ₂ are methyl groups, Claim No. The amphoteric surfactant betaine compound according to item 1.