JPH0657714B2 - Phosphobetaine - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION (Industrial field of application) The present invention is applicable to pharmaceutical bases, cosmetics and emulsifiers such as paints and inks, solubilizers, dispersants, cleaning bases, thickeners, etc. And a phosphobetaine composed of 2- (trialkylammonio) ethyl phosphate represented by the following general formula (1) having excellent antibacterial properties.

(Prior Art and Problems) While the development of a surfactant that causes less skin irritation is desired in the general formula, an antibacterial agent containing a substance having a broad antibacterial spectrum as an active ingredient is also always required. As shown in US Pat. No. 3,856,893, a phosphate ester-based surfactant having a phospholipid-like structure has been proposed. When this surfactant was examined in detail, this substance had an excellent surface-active ability, but its antibacterial property was not always sufficient.

(Means for Solving the Problems) Therefore, as a result of intensive studies in order to solve this problem, as a result, the phosphobetaine-based surfactant represented by the general formula described below has excellent surface activity and at the same time has a wide range. The inventors have found that they have a strong antibacterial spectrum and have completed the present invention.
Therefore, the object of the present invention is 2-
It is intended to provide a phosphobetaine composed of (trialkylammonio) ethyl phosphate.

That is, the present invention is the following general formula (1) (In the formula, R'is an alkyl group having 10 to 18 carbon atoms and R "and R is an alkyl group having 1 to 6 carbon atoms) and relates to phosphobetaine composed of 2- (trialkylammonio) ethyl phosphate.

(Detailed Description of the Invention) Phosphobetaine consisting of 2- (trialkylammonio) ethyl phosphate represented by the general formula (1) of the present invention is 2- (decyldimethylammonio) ethyl phosphate, 2- (Dimethyldecylammonio) ethylphosphate, 2- (diethyldodecylammonio) ethylphosphate, 2- (dodecylethylpropylammonio) ethylphosphate, 2- (dibutyldodecylammonio) ethylphosphate, 2- (dimethyltetradecylammonio) E) ethyl phosphate, 2- (diethyltetradecylammonio) ethyl phosphate, 2-
(Ethylpropyltetradecylammonio) ethylphosphate, 2- (dibutyltetradecylammonio) ethylphosphate, 2- (dimethylhexadecylammonio) ethylphosphate, 2- (diethylhexadecylammonio) ethylphosphate, 2- ( Dipropylhexadecylammonio) ethyl phosphate, 2-
Examples thereof include (dibutylhexadecylammonio) ethyl phosphate and 2- (dimethyloctadecylammonio) ethyl phosphate, but are not limited thereto. The phosphobetaine composed of 2- (trialkylammonio) ethyl phosphate represented by the general formula (1) of the present invention is produced, for example, as follows. The following formula (In the formula, R'is an alkyl group having 10 to 18 carbon atoms, R "and R are an alkyl group having 1 to 6 carbon atoms, and X is a halogenated (2-hydroxyethyl) represented by chlorine, iodine, bromine or fluorine) Trialkylammonium is converted to benzene (concentration is 1
˜40% by weight) in a solution
After gradually adding ˜4 times the molar amount of phosphorus oxychloride with stirring at room temperature, the stirring is continued for 2 to 30 hours. Then, the solvent is distilled off from the reaction solution, and the mixture is stirred at room temperature for 2 to 10 hours using water as a solvent. After the reaction, the pH of the reaction solution is adjusted to 6.0 with a base. Then, water is removed and desalted to obtain the desired phosphobetaine.

As the base, sodium hydroxide, potassium hydroxide, aqueous ammonia, triethanolamine and the like are applied.

Further, for desalting, an ion exchange membrane or an ion exchange resin is generally used, but depending on the purpose, it is also possible to use without desalting treatment.

The phosphobetaine of the present invention represented by the above general formula (1) and obtained in the examples described later was identified by the analytical values shown in Table 1 below.

(Examples) Hereinafter, the present invention will be described in detail with reference to Examples.

The parts shown in the examples mean parts by weight.

Example 1 Synthesis of 2- (dimethyldodecylammonio) ethyl phosphate 3.9 g (0.00) of dimethyldodecyl (2-hydroxyethyl) ammonium iodide in a 0.5 flask equipped with stirrer
(1 mol) is dissolved in 200 m of benzene, and 4.6 g (0.03 mol) of phosphorus oxychloride is gradually added dropwise at room temperature with stirring. After the dropping is completed, stirring is continued for 20 hours as it is.
After that, the solvent is removed by an evaporator, water is added to the residue, and the mixture is stirred at room temperature for 5 hours. After the reaction, the pH is adjusted to 6.0 with sodium hydroxide, and water is removed with an evaporator. Using the obtained residue as a sample, Soxhlet extraction is performed using ethanol as a solvent, and the solvent is distilled off from the ethanol extract. Furthermore, using the obtained residue as a sample, Micro Analyzer G-1100 (manufactured by Asahi Kasei)
After completely removing the inorganic ions by using, the mixture was recrystallized using a mixed solution of ethanol and ethyl acetate (2: 1) as a solvent to obtain 2.9 g of a white powder. The obtained white powder was confirmed to be 2% of the target compound from the analysis results shown in Table 1 below.
It was confirmed to be-(dimethyldodecylammonio) ethyl phosphate.

(Yield: 85%) Example 2 Synthesis of 2- (dimethyltetradecylammonio) ethyl phosphate Dimethyl (2-hydroxyethyl) tetradecylammonium iodide 0.01 instead of dimethyldodecyl (2-hydroxyethyl) ammonium iodide 0.01 By the same procedure as in Example 1 except that the moles were used, 3.0 g of a white powder was obtained.
From the analysis results shown in Table 1 below, it was confirmed that the obtained white powder was 2- (dimethyltetradecylammonio) ethyl phosphate as the target compound.

(Yield: 82%) Example 3 Synthesis of 2- (dimethylhexadecylammonio) ethyl phosphate Dimethylhexadecyl iodide (2-) instead of dimethyldodecyl (2-hydroxyethyl) ammonium iodide
By the same procedure as in Example 1 except that 0.01 mol of hydroxyethyl) ammonium was used, 2.9 g of a white powder was obtained.
It was confirmed from the analysis results shown in Table 1 below that the obtained white powder was 2- (dimethylhexadecylammonio) ethyl phosphate as the target compound. (Yield: 73%) Example 4 Synthesis of 2- (dimethyloctadecylammonio) ethyl phosphate Dimethyloctadecyl iodide (2-) instead of dimethyldodecyl (2-hydroxyethyl) ammonium iodide.
3.3 g of white powder was obtained by the same procedure as in Example 1 except that 0.01 mol of hydroxyethyl) ammonium was used.
From the analysis results shown in Table 1 below, it was confirmed that the obtained white powder was 2- (dimethyldodecylammonio) ethyl phosphate as the target compound. (Yield: 78%) Example 5 Synthesis of 2- (diethylhexadecylammonio) ethyl phosphate Diethylhexadecyl iodide (2-) instead of dimethyldodecyl (2-hydroxyethyl) ammonium iodide
3.5 g of white powder was obtained by the same procedure as in Example 1 except that 0.01 mol of hydroxyethyl) ammonium was used.
From the analysis results shown in Table 1 below, it was confirmed that the obtained white powder was 2- (diethylhexadecylammonio) ethyl phosphate as the target compound. (Yield: 83%) Example 6 Synthesis of 2- (dipropylhexadecylammonio) ethyl phosphate Dipropylhexadecyl iodide (2) instead of dimethyldodecyl (2-hydroxyethyl) ammonium iodide
By the same procedure as in Example 1 except that 0.01 mol of -hydroxyethyl) ammonium was used, 3.6 g of a white powder was obtained. It was confirmed from the analysis results shown in Table 1 below that the obtained white powder was 2- (dipropylhexadecylammonio) ethyl phosphate which was the target compound. (Yield: 75%) Example 7 Synthesis of 2- (dibutylhexadecylammonio) ethyl phosphate Dibutylhexadecyl iodide (2-) instead of dimethyldodecyl (2-hydroxyethyl) ammonium iodide
4.0 g of white powder was obtained by the same procedure as in Example 1 except that 0.01 mol of hydroxyethyl) ammonium was used.
From the analysis results shown in Table 1 below, it was confirmed that the obtained white powder was 2- (dibutylhexadecylammonio) ethyl phosphate as the target compound. (Yield: 83%) Example 8 Synthesis of 2- (ethylhexadecylpropylammonio) ethyl phosphate Ethylhexadecyl (2-hydroxyethyl) propyl iodide instead of dimethyldodecyl (2-hydroxyethyl) ammonium iodide By the same procedure as in Example 1 except that 0.01 mol of ammonium was used, 3.5 g of a white powder was obtained. From the analysis results shown in Table 1 below, it was confirmed that the obtained white powder was 2- (ethylhexadecylpropylammonio) ethyl phosphate as the target compound. (Yield: 80%) Example 9 Synthesis of 2- (butylethylhexadecylammonio) ethyl phosphate Butylethylhexadecyl iodide (2-hydroxyethyl) iodide instead of dimethyldodecyl (2-hydroxyethyl) ammonium iodide By the same procedure as in Example 1 except that 0.01 mol of ammonium was used, 3.6 g of white powder was obtained. From the analysis results shown in Table 1 below, it was confirmed that the obtained white powder was 2- (butylethylhexadecylammonio) ethyl phosphate as the target compound. (Yield: 80%) Experimental Example 1 This experimental example is for explaining the surface active property of the phosphobetaine according to the present invention.

The surface tension lowering ability and the foaming force of the phosphobetaines obtained in Examples 1 to 9 were measured. The same measurement was carried out using phosphobetaine (R = dodecyl) described in US Pat. No. 3,856,893 as a target substance for comparison. The surface tension was measured at 23.5 ° C using a Fischer surface tension meter. The surface tension of the phosphobetaine of the present invention is about 10% lower than that of the comparative substance. The foam height (super foam strength) is measured by the loss miles method (ASTMD1
178-53). The measurement results are shown in Table 2 below. High values indicate excellent foaming power.

Experimental Example 2 This experimental example is for explaining the antibacterial activity of phosphobetaine according to the present invention.

The antibacterial test was performed according to the method specified by the Japanese Society of Chemotherapy. The results are shown in Table 3.

(Effects of the Invention) As described above, the phosphobetaine of the present invention has excellent surface chemical properties as well as excellent antibacterial activity and is a cleaning base, emulsifier, solubilizer, and shampoo as a dispersant, a face-wash cream, and a skin cream. , Hair creams, hair treatments, foundations, creams, ointments, and other pharmaceutical bases and cosmetics, as well as oral hygiene agents, antibacterial fibers, antibacterial paints, antibacterial cleaners, athlete's foot remedies and cosmetics It can be applied widely as an ingredient.

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁵ Identification code Office reference number FI technical display location A61K 31/685 ADB 8314-4C

Claims (1)

[Claims] 1. The following general formula (1) (In the formula, R ′ is an alkyl group having 10 to 18 carbon atoms, R ″ and R are each having 1 to 6 carbon atoms), and phosphobetaine composed of 2- (trialkylammonio) ethyl phosphate.