JPH0443061B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention relates to a novel surface-active betaine compound and a method for producing the same. Recently, betaine compounds, which belong to amphoteric surfactants, have surface activity over a wide pH range and are compatible with anionic, cationic, and nonionic surfactants, so they are widely used in various industrial fields. It has reached the point where The present inventors 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/or propylene, n
is an integer from 1 to 50, and R'' is an alkyl group having 5 or less carbon atoms).The present invention proposes a surface-active betaine compound as a novel amphoteric surfactant. Active betaine compounds are synthesized by the following reaction: (1) ROH+n(R′O)→RO(R′O) _o H (However, R is an alkenyl group having 8 to 24 carbon atoms,
R' is ethylene and/or propylene group, n
is a positive integer of 1 to 50, R'' is an alkyl group having 5 or less carbon atoms, X is a halogen atom, and M is a monovalent alkali metal.) Reaction (1) is a higher alcohol having 8 to 24 carbon atoms, For example, octanol, decanol, lauryl alcohol, myristyl alcohol, cetyl alcohol,
1 to 1 mole of higher alcohol such as stearyl alcohol, behenyl alcohol, oleyl alcohol, oxo mixed alcohol having 11 to 15 carbon atoms, secondary alcohol having 12 carbon atoms, and tridecyl alcohol is mixed with 1 to 10% of ethylene oxide or/and propylene oxide by a known method. However, in terms of economy and usefulness, it is recommended to add 3 to 3 to 50 moles of ethylene oxide to 1 mole of higher alcohols such as lauryl alcohol, myristyl alcohol, tridecyl alcohol, and oxo-synthesized alcohols having 8 to 15 carbon atoms. Preferably, 10 moles are added. Also, adducts of only propylene oxide have no utility. Reaction (2) is to add 1 mol of the higher alcohol alkylene oxide adduct thus obtained to 1 mol of epihalogenhydrin, preferably epichlorohydrin or epibromohydrin, and a Lewis acid, preferably
BF ₃ , 40~ under normal pressure or pressurization under alllate catalyst
React at 140℃. Reaction (3) is the terminal halide 2 obtained in reaction (2).
1 mole of an alkylamine, such as methylamine, ethylamine, propylamine, butylamine, preferably methylamine, is added to 1 mole of an alkylamine such as methylamine, and the reaction is carried out at 50 to 100°C. However, before adding the amine, an alkali such as caustic potash, caustic soda 2 The reaction is more reliably carried out by adding moles and desalting to form an epoxide compound. Reaction (4) results in the tertiary amine compound thus obtained.
A monohalogen acetate, preferably monochloroacetic acid, is reacted at 50 to 100°C. The betaine compound of the present invention obtained in reaction (4) can be optionally dehydrated to obtain a purified product. Further, in reaction (4), 1 mol of alkali can be further added to obtain a metal salt composite. When the betaine compound of the present invention is purified, its IR spectrum (cm ^- ) is 3470, 2930,
Absorption is observed at 2870, 1640, 1600, 1470, 1270, and 1110. The betaine compound of the present invention is an excellent amphoteric surfactant and is used in industrial detergents, shampoos, foaming agents, AE agents, etc. Next, examples of the present invention will be shown. Example 1 450 g (1 mol) of poly(6)oxyethylene lauryl ether obtained by adding 6 mol of ethylene oxide to 1 mol of lauryl alcohol was placed in a four-necked kolben, and 0.5 g of BF ₃ etherate was added thereto.
92.5 g of epichlorohydrin while stirring to raise the temperature to ℃.
After 1 mol was gradually added dropwise over 30 minutes, the mixture was stirred at the same temperature for 8 hours. After that, caustic soda corresponding to the residual BF ₃ was added, the temperature was raised to 120℃, N ₂ gas was introduced, dehydration and deetherization were carried out, and then filtration (decatalyst) was carried out as a pale yellow liquid OHV104 at room temperature, lauryl poly(6) with a Cl content of 6.5%. Oxyethyl hydroxypropyl chloride 535g
I got it. Next, 434 g (0.8 mol) of lauryl poly(6) oxyethyl hydroxypropyl chloride was placed in a four-necked colben, 80 g of a 40% aqueous solution of caustic soda was added at 50°C, and then the temperature was raised to 70°C (0.4 mol of methylamine).
12.4 g was added and reacted for 5 hours, and further 97 g of a 50% aqueous solution of monochlorosodium acetate was added and reacted at 80°C for 6 hours. After that, N ₂ gas was introduced and dehydrated at 105℃, which turned into a pale yellowish brown liquid at room temperature, moisture 0.1%, Cl; 0.01%,
401 g of a surface-active betaine compound with N: 1.27% and pH (1%) of 6.7 was obtained. This product will be subjected to the tests described below. Example 2 544 g of poly(2) oxypropylene poly(5) oxyethylene myristyl ether, in which 2 moles of propylene oxide and 5 moles of ethylene oxide were added to 1 mole of myristyl alcohol, was placed in a four-necked colben, and 0.6 g of BF ₃ etherate was added thereto. The temperature was raised to .degree. C., and while stirring, 1 mole of epibromohydrin (127 g) was gradually added dropwise over 30 minutes, followed by stirring at the same temperature for 8 hours. Then add caustic soda corresponding to the residual BF ₃ .
The temperature was raised to 120°C, N ₂ gas was introduced, dehydration and etherification were carried out, and the mixture was filtered and turned into a pale yellow liquid at room temperature.
665 g of myristyl poly(2) oxypropyloxy, poly(5) ethyloxyhydroxypropyl bromide with OHV82.5 and Br: 11.7% was obtained. Next, 536.8 g (0.8 mol) of this material was placed in a four-necked Kolben, and a 40% aqueous solution of caustic soda was added at 50°C.
Add 18g of ethylamine and raise the temperature to 70℃ and add 0.4mol of ethylamine18
Then, 97 g of a 50% aqueous solution of sodium monochloroacetate was added and the reaction was carried out at 80° C. for 10 hours. After that, _N2 gas was introduced and the water was dehydrated at 105℃.
0.05%, Br: 0%, N: 1.08%, PH (1%) 6.8
512 g of surface active betaine compound 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 shows the solubility and surface activity of the compounds obtained in the examples. As shown in Table 2, the compounds of Examples 1 to 18 all have excellent surface activity.

【table】

【table】

【table】

[Table] Solubility is Examples 1 to 18: 1g, test solution: 99g
The state after mixing and at 20℃ is shown.

Claims (1)

[Claims] 1. The following general formula (R is an alkyl or alkenyl group having 8 to 24 carbon atoms, R' is an ethylene and/or propylene group, n is a positive integer of 1 to 50, and R'' is an alkyl group having 5 or less carbon atoms) 2. Polyoxyalkylene alkyl ether or polyoxyalkylene alkenyl obtained 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. 1 mole of ether is reacted with 1 mole of epihalogenhydrin to replace the terminal OH group with a [formula] group (where X is a halogen atom), and then reacted with 0.5 mole of an alkylamine having 5 or less carbon atoms and an alkali,
A method for producing an amphoteric surface-active betaine compound, which comprises reacting 1 mol of a monohalogen acetate with 1 mol of the obtained N-alkyl N,N-di(alkyl[polyalkyleneoxy], hydroxypropyl)amine. 3 In the general formula, R is laurin, tridecyl, tetradecyl, oleyl and a mixed alkyl group having 11 to 15 carbon atoms, R' is an ethylene group, n is an integer of 2 to 10,
The amphoteric surface-active betaine compound according to claim 1, wherein R'' is a methyl group.