JPS58180496A - L-arginine salt of phosphoric ester and emulsifying agent containing it - Google Patents

Abstract

NEW MATERIAL:A monoalkyl phosphate L-arginine salt shown by the formula (R is 8-36C alkyl, or alkenyl; R' is ethylene or propylene; n is 0-30). EXAMPLE:L-Anginine dodecyl phosphate. USE:An emulsifying agent, detergent, antistatic agent, or rust preventive. It forms an emulsion in a wide range irrespective of oil component, the emulsion is stable for aging, and causes neither crysatllization nor reduction in yield point and viscosity resulting from it. Having toxicity and skin irritation equal to or lower than those of an existing product. PROCESS:A monoalkyl phosphate is neutralized with L-arginine in equimolar amounts.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to an L-arginine salt of a phosphoric acid ester and an emulsifier containing the same.

Conventionally, phosphorous esters of organic hydroxy compounds having surface activity and their salts such as alkali metal salts and alkanolamine salts have been used as detergents, emulsifiers, antistatic agents,
It is widely used as ultrafine oil agents, rust preventives, lubricating oil additives, etc. In particular, monoalkyl phosphate ester salts are highly safe anionic surfactants with extremely low loin-like properties and dandruff-trapping properties, and are used in cleansers, other cosmetics, and perfumes that are used directly on the human body. It is known that Ichikawa raw materials and 17 are useful. However, it is known that conventionally known monoalkyl phosphoric acids are rapidly degraded, which is a fatal drawback for cosmetics.

Therefore, the present inventors conducted intensive studies to obtain a monoalkyl phosphate without the above-mentioned drawbacks, and found that L-arginine salt of a specific monoalkyl phosphate, Nisder, can be widely used regardless of the oil component. It forms a good emulsion over time, and the emulsion is extremely stable over time, and does not cause crystallization or an accompanying decrease in the yield value and viscosity of the yarn. The present invention was completed based on the discovery that the toxicity and skin irritation retrieval properties of this compound are the same or lower than those of acid ester salts.

That is, the present invention relates to the following general formula (1), (wherein R represents an alkyl or alkenyl group having 8 to 66 carbon atoms, R' represents an ethyne group or a propylene group, and n represents a number from ( ) to 60. ) A novel monoalkyl phosphate Nisdel L-
The present invention provides an arginine salt and an emulsifier containing the same.

Examples of the 7/' alkyl phosphate/L-arginine salt of the present invention represented by formula (1) include L-arzonine-octyl phosphate, L-arginine dodecyl phosphate, and L-arginine-tetradecyl. Phosphate, L-arginine hexadecyl phosphate, L-arginine octadecyl phosphate, L-arginine polyoxyethylene (5) dodecyl phosphate, L-arginine polyoxyethylene (3) tetradecyl phosphate, L-arzonine Examples include polyoxyethylene (7) octadecyl phosphate), L-fulginine/2-decyltetradecyl phosphate, L-arginine/2-dodecylhexadecyl phosphate, and the like.

These monoalkyl phosphate Nisdel llTll-arginine salts can be prepared by known methods (for example, JP-A-56-8619).
Nisder monoalkyl phosphate obtained by 1) and L-
The monoalkyl phosphate ester IL-arginine salt of the present invention, which can be easily obtained by neutralizing equimolar amounts of arginine, does not exhibit the desired effect of the present invention even when used alone as an emulsifier. However, it is more preferable to further combine this with a nonionic active agent having an HLB of 6 or less to form an emulsifier composition.

Nonionic activators with HLB 6 or less include polyoxyethylene alkyl ether, holoxyethylene fatty acid ester, polyoxyethylene sorbitan fatty acid nisder, polyoxyethylene rubi 1--/lJ]kilic acid ester, sorbitan fatty acid ester, glycerin Among nonionic surfactants such as fatty acid esters, those having an HLB of 6 or less can be mentioned.

The combination of Mata, monoalkyl phosphate ester @L-flujl' diphosphate and a nonionic activator with HLB 6 or less is 1
:10 to 2:1, particularly preferably 1:6 to 1:1.

To produce emulsified cosmetics using this emulsifier composition,
An L-arginine salt of a phosphoric acid ester, a nonionic active agent having an HLB of 6 or less, an oily base, and water may be emulsified in a conventional manner. Further, known cosmetic ingredients such as other types of surfactants, viscosity modifiers, medicinal agents, preservatives, humectants, colorants, fragrances, etc. can be added to this as necessary.

Examples of oily bases include hydrocarbons such as liquid paraffin, paraffin wax, ceresin, and squalane; waxes such as beeswax, heddle wax, and carnauba wax; natural *seed oils and fats such as olive oil, camellia oil, jojoba oil, and lanolin; Examples include silicone oil, B-containing acid, higher alcohol, and ester oil obtained by reacting these.

In addition, other types of surfactants include polyoxyethylene alkyl ether fatty acid ester, polyoxyethylene Rubitan Gekiden 11
71 ester, polyoxyethylene sorbitol fatty acid ester, polyoxyethylene hydrogenated castor oil alkyl sulfate ester, polyoxyethylene alkyl sulfate ester, alkyl phosphate ester, polyoxyethylene alkyl phosphoric acid alkali metal salt, sorbitan fatty acid ester, glycerin fatty acid Nisdel Polyvinyl alcohol, carboxyvinylbo IJ-r-, carboxymethylcellulose, polyvinylpyrrolidone, hydroxyethylcellulose, methylcellulose, and other high-molecular compounds are used as viscosity modifiers; natural products such as gelatin and tufted gum; alcohols such as ethanol and isozolopanol; The kind is
Medicinal agents include disinfectants, anti-inflammatory agents, vitamins, etc. Humectants include propylene glycol, glycerin, 1 r
3-':””ethylene glycol, sorbitol,
Examples of the preservative include lactic acid, sodium lactate, and sodium bimetridonecarboxylate. Further, examples of the preservative include paraoxybenzoic acid ester, benzoic acid, sodium benzoate, sorbic acid, potassium sorbate, and phenoxyethanol.

The emulsified cosmetic prepared using the compound (1) of the present invention is excellent in that it does not crystallize even when stored for a long period of time, and does not exhibit a decrease in yield or viscosity. In addition to being used as the emulsifier, the compound (1) of the present invention can also be used as a detergent, an antistatic agent, a rust preventive, and the like.

Next, the present invention will be explained with reference to Examples, but the present invention is not limited to these Examples.

(7) Example 1 In a 1 t beaker, monododecyl phosphate 2 7,
4 2, 9 (, 1st Shodoten Soyu 2 0 4. 6
4. Second equivalent point acid value 406.0, [), 1 mole) is 2
L]07! After dissolving 6 ml of methanol, add 200 ml of
L-arginine highly dissolved in ion-exchanged water of me 18
．． 1 8,! T' (0.1 mol) was added thereto and stirred at a temperature of 60 to 40'C for 15 minutes to obtain a slightly paste-like solidified product.

Next, the solvent was removed using a sieve, and the remaining solids totaled 200-
When washed with warm methanol 6 times with stirring, the state of the salt changed and a white powder was obtained. After filtration, dry under reduced pressure.
-White powder of arzonine dodecyl phosphate 4 3
．． 3 2 & (yield 95.0 items) was obtained.

Elemental analysis value practical 1] 1st shift: c 4 8.7s;, H
9. s%llJ12.3% Calculated value: 0 4
9. 1%, 896%. N12.7%I l( (KB
r) Figure 1 6400-3100, 2i0, 2850.168 [J.

1660, 1b40, 1450, 1170.1060-
.

950cIn-1 (8) iHNMIR (D20, external camphor TMS) 2nd
Figure δ ppm (, ii, )
D: 3.78 3Hlit
:4.35 2H13ONM
R [D20, internal standard zooxane] Figure 6 δ (
ppm): 1 77, 4(f), 1 59.7 (θ halo B.
6 (g) + 5 7. 1 (d) r43,4(
0) + 32.9 ~ 34.8 (blhJjlklt1
a+In) 2 5, 5 (n), 1 6.6 (Q) Example 2 In Example 1, monohexadecyl phosphate was replaced with monododecyl phosphate) 33.059 (first class). Point acid value 169.8, 2nd equivalent point acid value 345.7.0
．． Using 1 mol), the reaction and purification were carried out in the same manner as in Example 1, and L-arginino hexadecyl phosphate 4B, 679cW (95.0%) was obtained.

Actual elemental analysis value: 051.2%, H94, io, 8% Calculated value:
053.2CH, H99%lN11.3%IR(KBr
) 6400 to 3100, 2930, 2850, 1680° 1540.1470, 1450, 1410, 1050° 950.820.72-” Example 6 A weakly oily moisture cream (0/W type) having the following composition was produced. 7. The emulsification state, stability and yield value were investigated.The results are shown in Table 1.

■ Squalane 7.0■
Vaseline 6.0■
Setanol 2°0■
Lipophilic glyceryl monostearate 6.
0■ Butylparaben 0.
1■ Hexadecylphosphate) jf [(1st ff)
1.0 ■ Glycerin 4
・0■ Propylene glycol 6
,0 [phase] Methylparaben
0.10 Ice made by Kozue
Balance @ inspection fee
Small amount (v@manufacturing method) Heat and stir at 70-75°C to melt ■~■, gradually add ■~0 heated and dissolved at 70-75°C to emulsify, and immediately heat to 50°C. Cool to room temperature and add fragrance.Furthermore, while stirring to mix uniformly, cool to room temperature.

As is clear from the results, the cream using L-arginino hexadecyl phosphate of the present invention as an emulsifier did not crystallize over time and had good emulsification state and yield value.

[Brief explanation of drawings]

Fig. 1 is a drawing showing the infrared absorption spectrum of 1-alyanine 9-dodecyl phosphate of the present invention, Fig. 2 is a drawing showing the 1H nuclear magnetic resonance spectrum of the same substance, and Fig. 6 is a drawing showing the 130 nuclear magnetic resonance spectrum of the same substance. It is a drawing showing a resonance spectrum. Applicant: Kao Soap Co., Ltd.

Claims (1)

[Claims] 1. The following general formula (1), (wherein R represents an alkyl or alkenyl group having 8 to 66 carbon atoms, R' represents an ethylene group or a zolopyrene group, and n
represents a number from 0 to 60) monoalkyl phosphoric acid ester b l, −
arginine salt. 2. The following general formula (1), N1(2 (wherein, R is an alkyl or alkenyl group having 8 to 66 carbon atoms, R' is an ethylene group or a propylene group, and n
An emulsifier composition containing a monoalkyl phosphoric acid ester @L-alyanine salt represented by 6. The following general formula (1), (wherein R represents an alkyl or alkenyl group having 8 to 66 carbon atoms, R' represents an ethylene group or a propylene group, and n
represents a number from 0 to 30) An emulsifier composition containing a heptanoalkyl phosphoric acid ester-L-alyanine salt represented by the following formula and a nonionic active agent having an HLB of 6 or less.