JP3149964B2 - Novel phosphobetaine and method for producing the same - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel phosphobetaine useful as a base for hair and skin cosmetics, a detergent, an emulsifier, a conditioning agent and the like, and a method for producing the same.

[0002]

2. Description of the Related Art
Alkyl sulfates, polyoxyethylene alkyl sulfates, alkyl benzene sulfonates, etc. have been used as detergents, but since many of them have relatively high irritation to the skin, alkyl phosphates and acylated amino acid salts have recently been used. Cleaning agents that are less irritating to the skin such as hair,
It has come to be used as a detergent or emulsifier for skin cosmetics. However, recently, with the diversification of consumer needs and the trend toward luxury, in addition to low skin irritation,
It has been desired to develop a compound which has a conditioning effect such as giving a favorable feeling to the skin and hair, and which can be used by blending it with skin, hair cleansing agents and the like.

[0003]

Under these circumstances, the present inventors have conducted intensive studies and as a result, have found that a base for hair and skin cosmetics, which has low irritation to the skin and gives a favorable feel to the skin and hair, Novel phosphobetaine useful as an emulsifier, emulsifier, conditioning agent and the like and a method for producing the same have been found, and the present invention has been completed.

That is, the present invention provides a phosphobetaine represented by the general formula (I).

[0005]

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Here, R ¹ , R ² and R ³ are the same or different and each represent a linear or branched alkyl or alkenyl group having 1 to 24 carbon atoms, and at least ^one of R ¹ , R ² and R ³ One is an alkyl or alkenyl group having 5 to 24 carbon atoms. M represents the same or different and represents a hydrogen atom or a cation. m represents a number of 0 or more, and n represents a number of 1 or more. Here, m + n represents a number not exceeding the number of hydroxyl groups of the monosaccharide, oligosaccharide, sugar alcohol or glycerin, respectively. The present invention relates to a compound represented by the general formula (II):

[0007]

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The phosphoric ester represented by the general formula (II)
I)

[0009]

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[0010] The present invention provides a method for producing a phosphobetaine represented by the general formula (I), which comprises reacting an epoxy compound represented by the following formula:

As a compound similar to the novel phosphobetaine represented by the above general formula (I) according to the present invention, a sugar phosphobetaine having a short-chain alkyl group is already known (Japanese Patent Application Laid-Open No. 61-22096). . However, these compounds are significantly inferior in performance to the compound represented by the general formula (I) of the present invention, and therefore cannot be used as a conditioning agent which gives a good feeling to skin and hair. It has been found for the first time by the present invention that phosphobetaine having a long-chain alkyl group represented by the formula (I) has excellent performance as a detergent, an emulsifier and the like having a conditioning effect on hair, skin and the like. .

In the general formula (I), Z is m + n (m and n) of monosaccharide, oligosaccharide, sugar alcohol or glycerin.
Represents the above-mentioned meaning) is a residue excluding the hydroxyl group,
In this case, examples of the monosaccharide include allose, altrose, glucose, mannose, gulose, idose, galactose, talose, fructose, inositol, ribose, arabinose, xylose, lyxose, and ribulose. The monosaccharide may be modified with a suitable organic residue such as acylation, etherification, alkylene oxide addition, or acetalization, except for at least one of the hydroxyl groups.

Examples of oligosaccharides include maltooligosaccharides such as maltose, isomaltose, maltotriose, maltotetraose and maltoheptaose; cellooligosaccharides such as cyclodextrin and cellobiose;
Manno-oligosaccharides, fructooligosaccharides, sucrose, lactose and the like. In addition, the hydroxyl group of these oligosaccharides, except for at least one, may be modified with an appropriate organic residue such as acylation, etherification, alkylene oxide addition, and acetalization.

Further examples of sugar alcohols include sorbitol, mannitol, obtained by reducing a monosaccharide, and the like.
Examples include galactitol, xylitol, arabinitol, ribitol, and maltitol obtained by reducing oligosaccharides. In addition, those in which the hydroxyl group of these sugar alcohols is modified with an appropriate organic residue such as acylation, etherification, alkylene oxide addition, acetalization, etc., except for at least one may be used.

In the compound of the present invention represented by the above formula (I), R ¹ , R ² and R ³ represent a linear or branched alkyl or alkenyl group having 1 to 24 carbon atoms, and R ¹ , R ² , at least one of R ³ is an alkyl or alkenyl group having 5 to 24 carbon atoms. Examples of the linear or branched alkyl group or alkenyl group having 1 to 24 carbon atoms include methyl, ethyl, propyl, butyl, pentyl, hexyl,
Heptyl, octyl, nonyl, decyl, unenyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, heneicosyl, docosyl, tricosyl, tetracosyl, ethenyl, propenyl, butenyl,
Pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, dodecenyl, undecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, octadecenyl, nonadecenyl, eicosenyl, heneicosenyl, docosenyl, tricosyl, tricosenyl, ethylcotyl , Methylnonyl, methylundecenyl, methylheptadecyl, hexyldecyl, octyldecyl and the like.

The phosphobetaine of the present invention represented by the general formula (I) is obtained by reacting the phosphoric ester represented by the general formula (II) with an epoxy compound represented by the general formula (III). As the phosphate ester represented by the general formula (II), for example, glucose-1
-Phosphate, glucose-6-phosphate, mannose-1-
Phosphoric acid, mannose-6-phosphate, galactose-1-
Phosphoric acid, galactose-6-phosphate, fructose-1
-Phosphate, fructose-6-phosphate, fructose-
1,6-diphosphate, ribose-1-phosphate, xylose-
5-phosphate, inositol phosphate, sucrose phosphate, maltose phosphate, maltotriose phosphate, maltotetraose phosphate, maltopentaose phosphate, maltohexaose phosphate, maltoheptaose phosphate, cyclodextrin Inorganic or organic salts such as phosphoric acid, cellobiose phosphate, lactose phosphate, sorbitol phosphate, mannitol phosphate, galactitol phosphate, xylitol phosphate, arabinitol phosphate, ribitol phosphate, maltitol phosphate, glycerophosphate, etc. Salts are exemplified, and M in the general formula (II) is not particularly limited. Examples thereof include a hydrogen atom or an alkali metal, an ammonium group, an alkylammonium group, an acidic amino acid group, and a cationic residue of trialkanolamine.

The epoxy compound represented by the general formula (III) can be easily produced, for example, by reacting a corresponding trialkyl or alkenylamine with epihalohydrin according to a known method. In general formula (III)

[0018]

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Although is not particularly limited, examples thereof include a halogen atom and an anionic group of an alkyl sulfate.

Specific examples of the reaction of the present invention are as follows, for example.

[0021]

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(Wherein R ¹ , R ² , and R ³ have the same meanings as described above.) In order to carry out the production method of the present invention, a compound represented by the general formula (II)
0.1 to 10 with respect to the phosphate group of the phosphate ester represented by
The glycidyl trialkyl or alkenyl ammonium salt represented by the general formula (III) is reacted in a molar amount of 1 to 5 times, preferably 1 to 5 times. The reaction is carried out in the presence of an inert solvent at a temperature of 30 to 150C, preferably 40 to 90C.

As the inert solvent, for example, polar solvents such as water, methanol, ethanol, isopropanol, dimethylformamide, dimethylsulfoxide and the like, or a mixed solvent of two or more kinds thereof are used.
Among them, water or a mixed solvent of water and a lower alcohol is particularly preferred.

The reaction product includes, in addition to the phosphobetaine represented by the general formula (I), which is the object of the present invention, an inorganic salt as a by-product, an unreacted phosphate ester, a glycidyl trialkyl or alkenyl ammonium salt or a salt thereof. Contains epoxy ring-opened products. The proportion of each component in the reaction product depends on conditions such as the type of phosphate ester used, the type of glycidyl trialkyl or alkenyl ammonium salt, their reaction molar ratio, the type and amount of solvent used, and the reaction temperature. I do. Therefore, depending on the purpose of use, the reaction product can be used as it is, but if a higher purity product is required, for example, ion exchange chromatography, electrodialysis, solvent fractionation, recrystallization, etc. It may be appropriately purified and used by a known method.

[0025]

The novel phosphobetaine (I) of the present invention obtained as described above has an excellent conditioning effect on skin and hair, and can be used for shampoos, rinses,
It can be used for cosmetics and the like.

[0026]

EXAMPLES The present invention will be described in more detail with reference to the following examples, but the present invention is not limited to these examples.

Example 1 A reactor was charged with 35 g (0.1 mol) of α-D-glucose-1-phosphate monosodium salt tetrahydrate and 500 g of water.
The temperature was raised to ° C. Next, while maintaining the reaction system at 60 ° C., 78 g of glycidyl dimethyl octadecyl ammonium chloride
(0.2 mol) in a solution of 200 g of a 30% aqueous ethanol solution was gradually added dropwise, followed by reaction at 60 ° C. for 15 hours.
After completion of the reaction, the reaction solvent was removed under reduced pressure.
Washing with twice the volume of acetone removed unreacted glycidyldimethyloctadecyl ammonium chloride and its epoxy ring-opened product. The resulting crude product was purified by thin layer chromatography by recrystallization from ethanol to give a single spot, α-D-glucopyranose-1-.
33 g of [2-hydroxy-3- (N, N-dimethyl-N-octadecylammonio) propyl] phosphate were obtained (54% isolated yield).

¹ H-NMR (D ₂ O) (shown in FIG. 1);
88 (t, 3H, a ), 1.28 (broad, 30H, b ), 1.77 (m, 2H, c ),
3.18 (s, 6H, d ), 3.30 to 4.00 (broad m, 12H, e ), 4.40 (b
road, 1H, f ), 5.46 (m, 1H, g )

[0029]

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IR (KBr tablet method); shown in FIG.

Mass spectrometry (FAB ionization method); M / Z 614 (M + H)⁺  (M = C₂₉H₆₀O_TenNP) Example 2 A reactor was charged with α-D-glucose-1-phosphate monona
Add 35 g (0.1 mol) of thorium salt tetrahydrate and 500 g of water, and add 60 g
The temperature was raised to ° C. Next, while maintaining the reaction system at 60 ° C,
61 g of zyl dimethyl dodecyl ammonium chloride (0.2 g
Mol) dissolved in 200 g of water was slowly added dropwise.
Thereafter, the reaction was performed at 60 ° C. for 10 hours. After completion of the reaction, reactant solution
The reaction solvent was removed by freeze-drying. Obtained anti
The reaction product is washed with 10 volumes of acetone, and unreacted glycidyl
Dimethyl dodecyl ammonium chloride and its epoch
The xyl ring-opened product was removed. This is followed by ion exchange chromatography.
Fee (ion exchange resin: BIO RAD AG501-X8)
Thin-layer chromatography to give a single spot.
And purified from α-D-glucopyranose-1- [2-hydrogen
Roxy-3- (N, N-dimethyl-N-dodecyl ammonium
E) propyl] phosphate (22 g) was obtained (isolation yield: 42).
%).

¹ H-NMR (D ₂ O); δ (ppm) 0.88 (t, 3H, a ),
1.32 (broad, 18H, b ), 1.76 (m, 2H, c ), 3.18 (s, 6H, d ),
3.30 to 4.00 (broad, 12H, e ), 4.35 (broad, 1H, f ), 5.44
(m, 1H, g )

[0033]

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Mass spectrometry (FAB ionization method); M / Z 530 (M + H)⁺  (M = C_{twenty three}H₄₈O_TenNP) Example 3 A reactor was charged with α-D-glucose-1-phosphate monona
Add 35 g (0.1 mol) of thorium salt tetrahydrate and 500 g of water, and add 60 g
The temperature was raised to ° C. Next, while maintaining the reaction system at 60 ° C,
42 g of jyldimethylpentylammonium chloride (0.2 g
Mol) dissolved in 200 g of water was slowly added dropwise.
Thereafter, the reaction was performed at 60 ° C. for 10 hours. After completion of the reaction, reactant solution
The reaction solvent was removed by freeze-drying. Obtained anti
The reaction product is washed with 10 volumes of acetone, and unreacted glycidyl
Dimethylpentylammonium chloride and its epoch
The xyl ring-opened product was removed. This is followed by ion exchange chromatography.
Fee (ion exchange resin: BIO RAD AG501-X8)
And purified from α-D-glucopyranose-1- [2-hydrogen
Roxy-3- (N, N-dimethyl-N-pentylammonium
E) propyl] phosphate (13 g) was obtained (isolation yield: 31).
%).

¹ H-NMR (D ₂ O); δ (ppm) 0.89 (t, 3H, a ),
1.34 (broad, 4H, b ), 1.76 (m, 2H, c ), 3.19 (s, 6H, d ), 3.
29〜4.02 (broad, 12H, e ), 4.38 (broad, 1H, f ), 5.43 (m,
1H, g )

[0036]

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Mass spectrometry (FAB ionization method); M / Z 432 (M + H)⁺  (M = C₁₆H₃₄O_TenNP) Example 4 50 g of disodium α-glycerophosphate (0.23 mol
), 500 g of water and 230 g of 1N hydrochloric acid.
Was. Next, while maintaining the reaction system at 60 ° C, glycidyl dimethyl
95.1 g (0.46 mol) of rupentyl ammonium chloride
Was dissolved in 400 g of a 30% aqueous ethanol solution.
Drop in time. Then, keep the temperature at 60 ° C and carry out the reaction for 15 hours.
Was. After completion of the reaction, the solvent was distilled off under reduced pressure, and the residue was diluted 10 times.
Wash with unreacted glycidyl dimethylpe
Ammonium ammonium chloride and its epoxy ring opening
Things were removed.

The resulting crude product was washed with 80% aqueous ethanol and purified by thin layer chromatography to give a single spot, pure 2,3-dihydroxypropyl [2-hydroxy-3- (N , N-Dimethyl-N-pentylammonio) propyl] phosphate (25 g) was obtained (isolation yield: 35%).

¹ H-NMR (D ₂ O); δ (ppm) 0.87 (t, 3H, a ),
1.28 (broad, 4H, b ), 1.75 (m, 2H, c ), 3.17 (s, 6H, d ), 3.
30 to 3.90 (m, 11H, e ), 4.35 (broad, 1H, f )

[0040]

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Mass spectrometry (FAB ionization method); M / Z 344 (M + H)⁺  (M = C₁₃H₃₀O₇NP) Example 5 50 g of disodium α-glycerophosphate (0.23 mol
), 500 g of water and 230 g of 1N hydrochloric acid.
Was. Next, while maintaining the reaction system at 60 ° C, glycidyl dimethyl
166.5 g of ruhexadecyl ammonium chloride (0.46 g
Mol) was dissolved in 600 g of a 30% aqueous ethanol solution.
The solution is added dropwise in 3 hours. After that, keep the temperature at 60 ° C for 20 hours.
Responded. After completion of the reaction, the solvent was distilled off under reduced pressure to give a residue.
Was washed with 10 volumes of acetone to remove unreacted glycidyl
Tyl hexadecyl ammonium chloride and its
The oxy ring-opened product was removed. The crude product obtained is 90%
Rinsed with an aqueous solution of ethanol
Purify to give a single spot, pure 2,3-diethyl
Droxypropyl [2-hydroxy-3- (N, N-dimethyl
Tyl-N-hexadecylammonio) propyl] phosph
53 g (46% isolated yield) were obtained.

¹ H-NMR (D ₂ O); δ (ppm) 0.88 (t, 3H, a ),
1.28 (broad, 26H, b ), 1.75 (m, 2H, c ), 3.16 (s, 6H, d ),
3.30 ~ 4.00 (m, 11H, e ), 4.36 (broad, 1H, f )

[0043]

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Mass spectrometry (FAB ionization method); M / Z 498
(M + H) ⁺ (M = C ₂₄ H ₅₂ O ₇ NP) Example 6 A reactor was charged with 8.9 g (0.032 mol) of sodium salt of sorbitol phosphate prepared according to the following Synthesis Example 1 and 100 g of water.
Warmed to ° C. Next, while maintaining the reaction system at 60 ° C, glycidyl dimethyl hexadecyl ammonium chloride 17.4
g (0.048 mol) in 100 g of a 30% aqueous ethanol solution is added dropwise over 2 hours. Thereafter, the reaction was carried out at 60 ° C. for 10 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, and the residue was washed with 10 times the volume of acetone to remove unreacted glycidyldimethylhexadecyl ammonium chloride and its epoxy ring-opened product.

The resulting crude product was washed with a 90% aqueous ethanol solution, purified by thin layer chromatography to give a single spot, and pure 2,3,4,5,6-pentahydroxyhexyl [2 5.6 g of -hydroxy-3- (N, N-dimethyl-N-hexadecylammonio) propyl] phosphate was obtained (30% isolated yield).

¹ H-NMR (D ₂ O); δ (ppm) 0.87 (t, 3H, a ),
1.29 (broad, 26H, b ), 1.75 (m, 2H, c ), 3.16 (s, 6H, d ),
3.20 to 4.00 (m, 14H, e ), 4.34 (broad, 1H, f )

[0047]

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Mass spectrometry (FAB ionization method); M / Z 588 (M + H)⁺  (M = C₂₇H₅₈O_TenNP) Example 7 In a reactor, sorbitol resin prepared according to Synthesis Example 1 below was used.
Acid sodium salt 8.9 g (0.032 mol) and water 1
00 g was added and heated to 60 ° C. Next, keep the reaction system at 60 ° C.
While glycidyl dimethylpentyl ammonium chloride
Ride 10g (0.048 mol) to 100g 30% ethanol water
The solution dissolved in the solution is added dropwise over 2 hours. Then 60
The reaction was carried out for 9 hours while maintaining the temperature. After the reaction is completed,
The solvent was distilled off, and the residue was washed with 10 volumes of acetone.
Glycidyldimethylpentylammonium chloride
And its epoxy ring-opened product were removed.

The resulting crude product was washed with a 90% aqueous ethanol solution, purified by thin-layer chromatography until a single spot was obtained, and pure 2,3,4,5,6-pentahydroxyhexyl [2 -Hydroxy-3- (N, N-dimethyl-N-pentylammonio) propyl] phosphate
3.3 g were obtained (isolation yield 26%).

¹ H-NMR (D ₂ O); δ (ppm) 0.87 (t, 3H, a ),
1.28 (broad, 4H, b ), 1.75 (m, 2H, c ), 3.17 (s, 6H, d ), 3.
35 to 3.90 (m, 14H, e ), 4.35 (broad, 1H, f )

[0051]

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Mass spectrometry (FAB ionization method); M / Z 434 (M + H)⁺  (M = C₁₆H₃₆O_TenNP) Example 8 Maltose phosphoric acid synthesized according to Synthesis Example 2 below in a reactor
Disodium salt 47g (0.1 mol), water 400g and 1N hydrochloric acid
200 g was added, and the temperature was raised to 70 ° C. after stirring and dissolving. This is guri
122 g of sidyl dimethyl dodecyl ammonium chloride
(0.4 mol) in 300 g of water
After lowering, the reaction was carried out at 70 ° C. for 20 hours. After the reaction,
The reaction solvent was removed by freeze-drying from the product solution. Profit
Wash the reacted product with 10 volumes of acetone to remove unreacted
Ricidyl dimethyl dodecyl ammonium chloride
The epoxy ring-opened product was removed.

Thereafter, the mixture was purified by ion exchange chromatography (ion exchange resin: AG501-X8 manufactured by BIO RAD), and maltose [2-hydroxy-3- (N, N-dimethyl-N-dodecylammonio) propyl] was used. 35 g of phosphate were obtained (51% isolated yield).

¹ H-NMR (D ₂ O); δ (ppm)

[0055]

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Mass spectrometry (FAB ionization method); M / Z 692 (M + H)⁺  (M = C₂₉H₅₈O_FifteenNP) Example 9 Fructose-1,6-diphosphate trisodium salt in a reactor
Add 45 g (0.09 mol) of hexahydrate and 200 g of water, and raise to 60 ° C.
Warmed. Next, while maintaining the reaction system at 60 ° C.,
84 g of methylpentyl ammonium chloride (0.4 m
Solution) dissolved in 200 g of water was slowly dropped.
Thereafter, the reaction was performed at 60 ° C. for 20 hours. After completion of the reaction, reactant solution
The reaction solvent was removed by freeze-drying. Obtained anti
The reaction product is washed with 10 volumes of acetone, and unreacted glycidyl
Dimethylpentylammonium chloride and its epoch
The xyl ring-opened product was removed. This is followed by ion exchange chromatography.
Fee (ion exchange resin: AG 501-X8 manufactured by BIO RAD)
Until thin spot chromatography gives a single spot
And fructose-1,6-di [2-hydroxy-
3- (N, N-dimethyl-N-pentylammonio) pro
[Pyr] phosphate (32 g) was obtained (isolation yield: 52%).

¹ H-NMR (D ₂ O); δ (ppm) 0.88 (t, 6H, a ),
1.31 (broad, 8H, b ), 1.76 (m, 4H, c ), 3.19 (s, 12H, d ),
3.28 to 4.00 (broad, 19H, e ), 4.35 (broad, 2H, f )

[0058]

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Mass spectrometry (FAB ionization method); M / Z 683
(M + H)⁺  (M = C₂₆H₅₆O₁₄N_TwoP_TwoSynthesis Example 1 Sorbitol phosphate sodium salt is prepared by a known method.
(Japanese Patent Publication No. Sho 50-8052).

That is, 45.5 g of sorbitol was dissolved in 125 ml of water, and 38.4 g of phosphorus oxychloride was added dropwise thereto over about 2 hours while stirring at 0 to 5 ° C. At this time, 10
The pH of the reaction solution was always maintained at 13.5 by adding an aqueous solution of N-caustic soda, and alkali was added dropwise until no change in pH was observed even after the addition of phosphorus oxychloride was completed. The reaction mixture was neutralized using a cation exchange resin (Dowex 50 × 4H ⁺ type), concentrated under reduced pressure, and adjusted to pH 10 with an aqueous solution of sodium hydroxide. Next, 120 ml of ethanol was added and the mixture was cooled. The precipitated inorganic salt was filtered off, and the lower layer of the filtrate separated into two layers was separated. Add water to make 250ml,
Further, 1 liter of methanol was added, and the precipitated sodium salt of sorbitol phosphate was separated by filtration and dried.

This crude product was dissolved again in 100 ml of water, and ethanol was added to cause reprecipitation to obtain 45 g of purified sodium salt of sorbitol phosphate.

Synthesis Example 2 Disodium maltose phosphate was synthesized according to a known method (Japanese Patent Publication No. 50-8052).

That is, the reaction was carried out in the same manner as in Synthesis Example 1 except that 85.4 g of maltose was dissolved in 250 ml of water to obtain 60 g of purified maltose phosphate disodium salt.

Comparative Example 1 As a sugar phosphobetaine having a short-chain alkyl group, α-D-glucopyranose-1- [2
-Hydroxy- (N, N, N-trimethylammonio) propyl] phosphate was synthesized according to a known method (JP-A-61-2209).

That is, α-D-glucose-1-
100 g of disodium phosphate, 100 g of water and 70 g of 4N hydrochloric acid were added, and the temperature was raised to 60 ° C. A solution prepared by dissolving 160 g of glycidyltrimethylammonium chloride in 140 g of water was gradually added dropwise, followed by reaction at 60 ° C. for 4 hours. After completion of the reaction, the reaction solution was filtered to remove floating impurities. This solution is passed through an electrodialysis device to desalinate ionic impurities, and water is distilled off from the reaction solution to obtain α-D −
Glucopyranose-1- [2-hydroxy- (N, N, N-
77 g of trimethylammonio) propyl] phosphate were obtained.

Test Examples Using the compounds of the present invention obtained in Examples 1, 3 to 7 and 9, hair conditioning agents having the compositions shown in Table 1 were produced by the following methods, and the conditioning effects were examined by the following methods. In addition, the conditioning effects of the comparative products having the compositions shown in Table 1 were similarly examined. Table 1 shows the results.

<Production Method> Each component was added to water heated to 70 ° C., and the mixture was stirred and mixed, and then cooled to room temperature with stirring to obtain a hair conditioning agent.

<Evaluation method> 20 g of hair (15 cm in length) of a Japanese woman who has not been subjected to beauty treatment such as cold perm or bleach are bundled, and this hair bundle contains an anionic activator as a main component. After washing with a commercially available shampoo, 2 g of various hair conditioning agents having the compositions shown in Table 1 were applied uniformly, then rinsed with running water for 30 seconds, and then towel dried. The hair bundle in the wet state was subjected to a sensory evaluation for flexibility, smoothness and moist feeling. The evaluation criteria were ◎ for particularly excellent, ○ for good, △ for ordinary, and × for poor.

[0069]

[Table 1]

[Brief description of the drawings]

FIG. 1 shows the ¹ H- of α-D-glucopyranose-1- [2-hydroxy-3- (N, N-dimethyl-N-octadecylammonio) propyl] phosphate obtained in Example 1.
It is an NMR spectrum figure.

FIG. 2 is an IR spectrum of α-D-glucopyranose-1- [2-hydroxy-3- (N, N-dimethyl-N-octadecylammonio) propyl] phosphate obtained in Example 1.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI B01F 17/14 B01F 17/14 (56) References JP-A-61-22096 (JP, A) (58) Fields investigated (Int. .Cl. ⁷ , DB name) C07F 9/10 C07H 11/04 CA (STN) CAOLD (STN) REGISTRY (STN)

Claims (6)

(57) [Claims] 1. A phosphobetaine represented by the general formula (I). Embedded image Here, R ¹ , R ² , and R ³ are the same or different and each represent a linear or branched alkyl group or alkenyl group having 1 to 24 carbon atoms,
At least one of R ¹ , R ² and R ³ is an alkyl or alkenyl group having 5 to 24 carbon atoms. M represents the same or different and represents a hydrogen atom or a cation. m represents a number of 0 or more, and n represents a number of 1 or more. However,
m + n represents a number not exceeding the number of hydroxyl groups of the monosaccharide, oligosaccharide, sugar alcohol or glycerin, respectively. ] 2. The phosphobetaine according to claim 1, wherein m is 0 in the general formula (I). 3. In the general formula (I), m is 0, and Z is a residue remaining after removing n (n has the above-mentioned meaning) hydroxyl groups from glucose or fructose. 2. The phosphobetaine according to 2. 4. In the general formula (I), m is 0 and Z is a residue remaining after removing n (n has the above-mentioned meaning) hydroxyl groups from sorbitol. Phosphobetaine. 5. In the general formula (I), n (n is as defined above) hydroxyl groups are excluded from maltooligosaccharides, sucrose or lactose in which m is 0 and Z is less than 10 in the degree of condensation. 3. The phosphobetaine according to claim 2, which is a residue remaining. 6. A compound of the general formula (II) The phosphoric ester represented by the general formula (III) Wherein an epoxy compound represented by the general formula (I) is reacted: [Wherein, Z, R ¹ , R ² , R ³ , M, m, and n have the same meaning as described above. ] The manufacturing method of the phosphobetaine represented by these.