JPH06247826A - Moisturizer and cosmetic and cleaning composition containing the same - Google Patents

Abstract

(57) [Summary] [Structure] The following general formula (1) [In the formula, Z is a residue obtained by removing n hydroxyl groups from glycerin or a glycerin condensate or HO-A- (A is a carbon number of 1 to
A humectant consisting of carboxybetaine represented by the formula 5)], and a cosmetic or cleaning composition containing the same. [Effect] It has an excellent moisturizing effect that gives a moist feel to hair and skin, and the effect does not disappear easily.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a moisturizing agent and its use. More specifically, it is a moisturizing agent comprising specific carboxybetaine useful for hair cosmetics, skin cosmetics, etc., and cosmetics and detergent compositions containing the same. Regarding

[0002]

2. Description of the Related Art Conventionally, the problems to be solved by the invention
Various moisturizers are added to many shampoos, rinses, cosmetics and the like in order to impart a moist feel to hair and skin. Usually, glycerin, propylene glycol, sorbitol, urea, alkylene oxide adducts of sugars, etc. are used as the moisturizer.

However, none of these moisturizers are satisfactory in moisturizing properties and touch, and they easily diffuse and flow out due to sweat or water, and their effects do not last. Furthermore, in a type of cosmetics such as rinses and body rinses that are used after washing, or in a detergent containing a large amount of a surfactant, most of them are washed away, and the original effect is often not sufficiently exhibited.

Therefore, it has excellent moisturizing properties, touch properties, etc.,
Moreover, it has been desired to develop a compound having a long-lasting moisturizing effect even after being rinsed off with sweat or water.

[0005]

Means for Solving the Problems The inventors of the present invention have made extensive studies in view of the above-mentioned circumstances, and as a result, the carboxybetaine compound described below has an excellent moisturizing property, and further, the above-mentioned effects are long when used in various cosmetics and detergents. The inventors have found that it lasts over time, and have completed the present invention.

That is, the present invention provides the following general formula (1)

[0007]

[Chemical 2]

[In the formula, Z is a residue obtained by removing n hydroxyl groups from glycerin or a glycerin condensate, or HO-A- (A
Represents a linear or branched alkylene group having 2 to 5 carbon atoms), R ¹ and R ² are the same or different, and are linear or branched alkyl having 1 to 5 carbon atoms. Represents a group, Y represents a linear or branched alkylene group which may have a hydroxyl group, n is 1 or more, and represents a number not exceeding the number of hydroxyl groups of glycerin or glycerin condensate,
The present invention provides a moisturizing agent comprising carboxybetaine represented by the formula [1] when Z is HO-A-], and a cosmetic and detergent composition containing the carboxybetaine.

In the general formula (1), as a preferable example of Z,
Is a 2,3-dihydroxypropyl group, 2,6,7-to
Lihydroxy-4-oxaheptyl group, HOCH₂CH (OH) CH₂
O- (CH ₂CH (OH) CH₂O)_m-CH₂CH (OH) CH₂-(M is a number from 1 to 10
A polyglycerin group represented by
Ciethyl group, 3-hydroxypropyl group, 4-hydroxy
Examples include a cibutyl group and a 5-hydroxypentyl group.
It

In the general formula (1), preferable examples of R ¹ and R ² include a methyl group, an ethyl group, a propyl group, a butyl group and a pentyl group.

In the general formula (1), preferable examples of Y include methylene group, ethylene group, trimethylene group, tetramethylene group, pentamethylene group, hydroxyethylene group and hydroxymethylmethylene group.

Particularly, the carboxybetaine (1) used in the present invention preferably satisfies the following formula.

[0013]

[Equation 2]

Specifically, the following (1-1) to (1-8)
Is mentioned.

[0015]

[Chemical 3]

Among these, particularly preferable carboxybetaines are p in the above formula (1-1), and q
There is one.

Carboxybetaine used in the present invention (1)
Can be produced, for example, according to the following reaction formula.

[0018]

[Chemical 4]

(In the formula, X represents a halogen atom, M represents a cation, and Z, R ¹ , R ² , Y, and n have the same meanings as described above.)

Preferred examples of the compound represented by the general formula (2) include a glycidyl etherified glycerin or glycerin condensate obtained by reacting a condensate of glycidol, glycerin or glycerin with epihalohydrin and a dialkylamine. Examples thereof include compounds obtained by the reaction and dialkylalkanolamines.

In the general formula (3), X includes a fluorine atom, chlorine atom, bromine atom, iodine atom and the like, and M includes Na ⁺ , K ^{+ and the} like.

To carry out the above reaction, 1 to 5 times, preferably 1 to 2 times, the amount of the compound (3) is added to the compound (2) in the presence of an inert solvent at 20 to 120 ° C., preferably. May be reacted at 40 to 90 ° C.

As the inert solvent used in the above reaction, water, methanol, ethanol, isopropanol,
Examples thereof include polar solvents such as dimethylformamide and dimethylsulfoxide, and two or more kinds of mixed solvents selected from these, and among these, lower alcohols and mixed solvents of water and lower alcohols are preferable.

Carboxybetaine used in the present invention (1)
The moisturizing agent consisting of is excellent in moisturizing feel when applied to hair and skin, and since it lasts for a long time, it is applied to various uses, that is, cosmetics and detergent compositions.

The cosmetic of the present invention preferably contains carboxybetaine (1) in an amount of 0.1 to 20% by weight (hereinafter simply referred to as "%"), particularly 0.5 to 10%.

In the cosmetic of the present invention, in addition to the above-mentioned carboxybetaine (1), components used in ordinary cosmetics, for example, ethylene glycol, diethylene glycol, triethylene glycol, and higher polyethylene glycols, propylene glycol, dipropylene. Glycol,
Further polypropylene glycols, 1,3-butylene glycol, butylene glycols such as 1,4-butylene glycol, glycerin, diglycerin, further polyglycerins, sorbitol, mannitol,
Sugar alcohols such as xylitol and maltitol, ethylene oxide (hereinafter abbreviated as EO) adduct of glycerins, propylene oxide (hereinafter abbreviated as PO) adduct, EO and PO adducts of sugar alcohols, galactose, glucose, fructose, etc. Monosaccharides and their EO and PO adducts,
Polysaccharides such as maltose and lactose and polyhydric alcohols such as EO and PO adducts; hydrocarbons such as liquid paraffin, squalane, vaseline and solid paraffin, natural oils and fats such as olive oil, jojoba oil, evening primrose oil, coconut oil and beef tallow ,
Isopropyl myristate, cetyl isooctanoate, ester oils such as neopentyl glycol dicaprate, silicone oils such as dimethyl silicone and methylphenyl silicone, oily components such as isostearic acid and higher fatty acids such as oleic acid; polyoxyethylene (hereinafter , Abbreviated as “POE”) alkyl ether, POE branched alkyl ether, POE sorbitan ester, POE
Nonionic surfactant such as glycerin fatty acid ester, POE hydrogenated castor oil, sorbitan ester, glycerin fatty acid ester, polyglycerin fatty acid ester, anionic surfactant such as phosphoric acid type, sulfonic acid type, sulfuric acid type, carboxylic acid type Agents, other amphoteric surfactants, cationic surfactants, etc .; vitamins, bactericides such as triclosan, trichlorocarban, dipotassium glycyrrhizinate,
Anti-inflammatory agents such as tocopherol acetate, zinc pyrithione,
Anti-dandruff agents such as octopirox, activators, cooling agents such as menthol, agents such as UV absorbers; methylparaben,
Preservatives such as butylparaben, inorganic salts, viscosity modifiers such as polyethylene glycol stearate ethanol, pearling agents, fragrances, pigments, antioxidants; water-swelling clays such as montmorillonite, saponite, hecklite, bee gum, kunivia, smecton Minerals; Polymers such as carrageenan, xanthan gum, sodium alginate, pullulan, methylcellulose, carboxymethylcellulose, hydroxyethylcellulose, hydroxypropylcellulose and other polysaccharides, carboxyvinyl polymers, polyvinylpyrrolidone and other synthetic polymers; titanium oxide, kaolin, mica Inorganic pigments such as sericite, zinc white, and talc, and pigments such as polymethylmethacrylic acid and polymer powder such as nylon powder may be appropriately blended within a range that does not impair the effects of the present invention. Kill.

The cosmetic composition of the present invention can be produced by a usual method, and its dosage form can be any liquid form, creamy form, solid form, powder form, etc., but especially liquid form or It is preferably creamy.

The detergent composition of the present invention contains carboxybetaine (1) in an amount of 0.5 to 50%, particularly 1 to 30.
% Is preferably contained.

In the detergent composition of the present invention, various surfactants usually used in detergents can be optionally used within the range not impairing the effects of the present invention.

Specifically, as anionic surfactants, for example, as sulfates and sulfonates,
Alkyl sulfate, polyoxyethylene alkyl sulfate,
Sulfosuccinic acid type, taurate type, isethionate type,
Examples of the surfactant include α-olefin sulfonic acid-based surfactants, examples of the carboxylate-based surfactant include fatty acid soap, ether carboxylic acid-based surfactant, and acylated amino acid-based surfactant, and examples of the phosphate-based surfactant include alkyl. Examples thereof include phosphoric acid ester-based surfactants.

Examples of the amphoteric surfactant include carbobetaine-based, phosphobetaine-based, sulfobetaine-based and imidazolinium betaine-based amphoteric surfactants.

As the nonionic surfactant, polyoxyalkylene addition type, polyoxypropylene / polyoxyethylene addition type, amine oxide type, mono- or diethanolamide type, other sorbitan fatty acid ester, glycerin fatty acid ester, sucrose fatty acid are used. Examples thereof include esters, alkyl saccharide-based sugars, N-polyhydroxyalkyl fatty acid amide-based sugars, and polyhydric alcohols.

Examples of the cationic surfactants include mono- or di-alkyl addition type quaternary ammonium salts having a linear or branched alkyl group and those obtained by adding alkylene oxide to the alkyl group.

These surfactants may be used alone or in combination of two or more, and the compounding amount thereof may vary depending on the dosage form, but is 2 to 60%, particularly 10% in the detergent composition of the present invention.
-50% is preferable. In addition, carboxybetaine (1)
To 1: 2 to 1:50 by weight, in particular 1: 3 to 1:
A range of 30 is preferable.

In the detergent composition of the present invention, in addition to the above-mentioned components, components used in ordinary detergents, for example, ethylene glycol, diethylene glycol, triethylene glycol, further polyethylene glycols, propylene glycol, dipropylene. Glycols, polypropylene glycols higher than them, butylene glycols such as 1,3-butylene glycol and 1,4-butylene glycol, glycerin, diglycerin, further polyglycerins, sorbitol, mannitol, xylitol, maltitol, etc. Sugar alcohols, EO or PO adducts of glycerins, EO or PO adducts of sugar alcohols, monosaccharides such as galactose, glucose and fructose and their EO or PO adducts, and polysaccharides such as maltose and lactose. Polyhydric alcohols such as EO or PO adducts; hydrocarbons such as liquid paraffin, squalane, vaseline, solid paraffin, natural oils such as olive oil, jojoba oil, evening primrose oil, coconut oil and beef tallow, isopropyl myristate, cetyl isooctano Ate, ester oils such as neopentyl glycol dicaprate, silicone oils such as dimethyl silicone and methylphenyl silicone, oily components such as higher fatty acids such as isostearic acid and oleic acid; fungicides such as vitamins, triclosan and trichlorocarban, glycyrrhizin Anti-inflammatory agents such as dipotassium acid and tocopherol acetate, antidandruff agents such as zinc pyrithione and octopirox, activators, cooling sensation agents such as menthol, agents such as ultraviolet absorbers; montmorillonite, saponite, hecklite, bee gum, kunibia Water-swellable clay minerals, such as Sumecton; carrageenan, xanthan gum,
Sodium alginate, pullulan, methylcellulose,
Polysaccharides such as carboxymethyl cellulose, hydroxyethyl cellulose and hydroxypropyl cellulose, polymers such as carboxyvinyl polymer and synthetic polymers such as polyvinylpyrrolidone; inorganic pigments such as titanium oxide, kaolin, mica, sericite, zinc white, talc, etc. Pigments such as polymethylmethacrylic acid and polymer powder such as nylon powder; preservatives such as methylparaben and butylparaben; inorganic salts, polyethylene glycol stearate,
Viscosity modifiers such as ethanol; Pearling agents; Fragrances; Dyes;
Antioxidants and the like can be appropriately added within a range that does not impair the effects of the present invention.

The detergent composition of the present invention can be produced by an ordinary method, and its dosage form can be any dosage form such as liquid, paste, solid, and powder. It is particularly preferable that the liquid or paste is used.

[0037]

EFFECT OF THE INVENTION The moisturizing agent of the present invention and the cosmetic and detergent compositions containing the same have an excellent moisturizing effect which gives a moist feel to hair and skin. Moreover, the effect is not easily lost by perspiration or water, even if washed off.

[0038]

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

Reference Example 1 Production of N, N-dimethyl-N- (2,3-dihydroxypropyl) -glycine

[0040]

[Chemical 5]

A 50% aqueous dimethylamine solution 18 was added to the reactor.
0 g (2.0 mol) was added, and 74 g of glycidol (1.
(0 mol) was added dropwise over 40 minutes, and the mixture was further reacted for 1 hour at room temperature. Then, the temperature is gradually raised, and at 50 ° C., water and excess dimethylamine are distilled off under a nitrogen gas stream, and then dried under reduced pressure to obtain crude N, N-dimethyl-N- (2,3-dihydroxypropyl). ) Obtained the amine. 61.5 g (0.5 mol) of the obtained amine and 120 g of water were placed in a reactor, and 116.5 g (1.0 mol) of sodium chloroacetate was added.
The aqueous solution was added dropwise over 40 minutes, after which the temperature was gradually raised to 6
The reaction was carried out at 0 ° C for 1 hour. After the reaction is completed, the solvent is subjected to ion exchange chromatography (ion exchange resin: BIORA
D501 AG501-X8) and the solvent was distilled off under reduced pressure to obtain 25 g of the title compound (yield 75%).

Reference Example 2 Production of N, N-dimethyl-N- (2,6,7-trihydroxy-4-oxaheptyl) -glycine

[0043]

[Chemical 6]

90% dimethylamine 50% aqueous solution was added to the reactor.
0 g (10.2 mol) was added, and 2,3-dihydroxypropyl 2,3-epoxypropyl ether 1 was added at room temperature.
126 g (7.6 mol) was added dropwise over 3 hours. After dropping
The temperature was raised for removal, and the mixture was reacted at 50 ° C. for 4 hours. After the reaction was completed, residual dimethylamine and water were removed under reduced pressure to obtain 1482 g of a crude product. To this, 1000 g of water was added and dissolved, and a solution in which 1000 g (8.7 mol) of sodium chloroacetate was dissolved in 1000 g of water was added dropwise over 5 hours while maintaining the reaction system at 60 ° C. Then, it was made to react at 60 degreeC for 5 hours. After completion of the reaction, as it is, ion exchange chromatography (ion exchange resin: manufactured by BIORAD)
AG501-X8) and the solvent was distilled off under reduced pressure to obtain 1241 g of the title compound (yield 65%).

Reference Example 3 Production of N, N-dimethyl-N-hydroxyethyl-glycine

[0046]

[Chemical 7]

89.1 g (1.0 mol) of water, 100 g of N, N-dimethylethanolamine was placed in the reactor, and 134.0 g (1.15 mol) of sodium chloroacetate aqueous solution was added.
It dripped over time. After the dropping, the temperature was gradually raised to 70 ° C. and the reaction was carried out for 8 hours. After completion of the reaction, the solution was purified by ion exchange chromatography (ion exchange resin: AG501-X8 manufactured by BIO RAD), and the solvent was distilled off under reduced pressure to obtain 113.2 g of the title compound (yield 77%).

Reference Example 4 Production of N, N-dimethyl-N-hydroxypropyl-glycine

[0049]

[Chemical 8]

After adding 300 g (2.9 mol) of N, N-dimethylpropanolamine and 320 g of water to the reactor,
The temperature was raised to 55 ° C and 407 g of sodium chloroacetate was added.
A solution of (3.5 mol) in 450 g of water was added dropwise over 2.5 hours. Then, while maintaining this at 55 ℃,
The mixture was stirred for 8 hours. After completion of the reaction, as it is, ion exchange chromatography (ion exchange resin: BIO RA
D501 AG501-X8) and the solvent was distilled off under reduced pressure to obtain 380 g of the title compound (yield 81%).

Reference Example 5 Production of N, N-dimethyl-N-hydroxyethyl-β-alanine

[0052]

[Chemical 9]

Sodium chloropropionate 4 in the reactor
Add 100 g of 3.3 g (0.33 mol) ethanol,
20 g (0.22 mol) of N, N-dimethylethanolamine was added dropwise over 1 hour. After dropping, the temperature is raised to remove, and 8
The reaction was carried out at 0 ° C for 26 hours. After the reaction was completed, the solution was concentrated to dryness, 300 ml of methanol was added, and the insoluble matter was filtered off.
After that, the solvent was distilled off, 300 g of water was added, and the mixture was purified by ion exchange chromatography (ion exchange resin: AG501-X8 manufactured by BIO RAD), and the solvent was distilled off under reduced pressure to obtain 12.4 g of the title compound. Rate 34.3%).

Example 1 (Evaluation of Moisture Retention and Touch) Compounds 1-5 and Comparative Compound 1 obtained in Reference Examples 1-5
About 4 to 4, the moisturizing ability and the touch feeling were evaluated by the following methods. The results are shown in Table 1.

Method for evaluating moisturizing ability: A 2% aqueous solution of each sample was prepared, and 10 μl of the sample solution was applied to 1 cm ^{2 of} the human forearm flexion side, which was conditioned at 20 ° C./40% RH, and left for 10 minutes. Before and after this process
Using -200 (manufactured by IBS Co., Ltd.), the skin conductance is measured, and the moisturizing ability is determined from the ratio of the conductance before and after the treatment. Here, the moisturizing ability is represented by conductance after treatment / conductance before treatment. The above operation 1
Repeated 0 times and the result is shown as an average value. After that, the treated site was rinsed with running water, towel-dried, and allowed to stand for 10 minutes, and the skin conductance was measured in the same manner to determine the moisturizing ability after rinsing. Here, the moisturizing ability after rinsing is represented by conductance after rinsing / conductance before rinsing.

Tactile evaluation method: A 10% aqueous solution of each sample was prepared, and 200 μl of each of 10 panelists was evenly applied to the flexion side of each forearm and left for 3 minutes. Then, the application site was touched with the palm and the moist feeling and the sticky feeling were evaluated according to the following criteria.

(Moisture) ○: Moist. Δ: Slightly moist. ×: Not moisturized.

(Stickiness) ○: No stickiness is felt. Δ: A little sticky is felt. X: Feels sticky. The results are the average of the evaluations of the 10 panelists.

[0059]

[Table 1]

As is clear from the results shown in Table 1, all the products of the present invention have an excellent moisturizing ability, and they are retained even after rinsing, and further, they have a good moist feeling and stickiness. It turns out that it is what gives the lack.

Example 7 A paste-like face wash having the following composition was prepared by a conventional method.

[0062]

(Composition) (% by weight) Sodium sesquilauryl phosphate 25 Dipotassium myristyl sulfosuccinate 5 Cocoyl diethanolamide 2 Polyethylene glycol monostearate 4 Compound of Reference Example 1 5 Carboxyvinyl polymer 0.5 Paraben 0.3 Perfume 0 .3 Purified water balance

The obtained facial cleanser was refreshed after washing and had a moist feeling.

Example 3 A liquid body shampoo having the following composition was prepared by a conventional method.

[0065]

[Table 3] (Composition) (wt%) Lauryl phosphate triethanolamine 20 Alkyl saccharide [C ₁₂ -O- (G) _2.5 ] ^{* 1} 5 Lauroyl sarcosine sodium 5 Compound of Reference Example 3 8 Xanthan gum 0.5 Propylene glycol 3 Perfume 0.7 Purified water balance * 1: C ₁₂ is a lauryl group and G is glucose.

This body shampoo did not cause bulkiness even after washing, and had a moist feeling.

Example 4 An anti-dandruff shampoo having the following composition was prepared by a conventional method.

[0068]

[Table 4] (Composition) (% by weight) Lauryl dimethylamine acetic acid betaine 10 N-lauroyl glutamate sodium 10 Piroctone auramine (Octopirox, Hoechst) 0.5 Ethylene glycol distearate 2 Compound of Reference Example 3 5 fragrance 0.5 water balance

This anti-dandruff shampoo did not have a squeaky feeling when washing and rinsing hair, was not sticky after washing, and was moist, and the feeling was maintained.

Example 5 A dishwashing detergent having the following composition was prepared by a conventional method.

[0071]

(Table 5) (Composition) (wt%) polyoxyethylene (4) sodium lauryl ether sulfate 8 polyoxyethylene (20) myristyl ether 5 lauryl dimethylamine oxide 3 ethanol 3 compound of Reference Example 2 perfume 0.1 water balance

The dishwashing detergent was moist with less bulkiness on the hands after use, and the touch was maintained.

Example 6 A hair treatment having the following composition was prepared by a conventional method.

[0074]

[Table 6] (Composition) (wt%) 2-dodecylhexadecyltrimethylammonium chloride 2 Stearyl trimethylammonium chloride 2 Compound of Reference Example 5 Stearyl alcohol 5 Lanolin 3 Liquid paraffin 3 Polypeptide (collagen hydrolyzate) 5 Hydroxyethylcellulose (1% aqueous solution viscosity 8,000cp) 0.5 polyethylene (5) oleyl ether 0.5 methyl paraben 0.2 perfume 0.4 water balance

This hair treatment had an excellent effect of imparting softness to the hair, was not sticky, and gave a moist feel, and it lasted for a long time.

Example 7 A lotion having the following composition was prepared by a conventional method.

[0077]

Table 7 (Composition) (wt%) Lactic acid 0.03 Sodium lactate 0.84 Compound of Reference Example 5 5 Glycerin 2 Polyoxyethylene oleyl ether (20EO adduct) 1 Ethanol 10 Perfume 0.3 Water balance

The lotion did not lose its moisturizing ability due to sweat, was not sticky, and had a moist feeling, and it was lasting.

Example 8 A powder bathing agent having the following composition was prepared by a conventional method.

[0080]

Table 8 (Composition) (wt%) Sodium hydrogen carbonate 67 Dextrin 30 Compound 2 of Reference Example 5 Perfume 0.5 Dye 0.5

The powder bathing agent had an excellent moisturizing effect on the skin and gave a moist feeling, and it lasted for a long time.

 ─────────────────────────────────────────────────── --- Continuation of the front page (72) Inventor Tomohito Kitsuki 1450 Nishihama, Wakayama, Wakayama Kao Suisensha, Room 222 (72) Masatoshi Arisawa 523-8, Oyama, Matsudo, Chiba

Claims (4)

[Claims] 1. The following general formula (1): [In the formula, Z is a residue obtained by removing n hydroxyl groups from glycerin or a glycerin condensate or HO-A- (A is a carbon number of 2 to 2).
5 represents a straight chain or branched chain alkylene group), R ¹ and R ² are the same or different and represent a straight chain or branched chain alkyl group having 1 to 5 carbon atoms, and Y Represents a linear or branched alkylene group which may have a hydroxyl group, n is 1 or more and represents a number not exceeding the number of hydroxyl groups of glycerin or a glycerin condensate, and Z is HO-A-.
A humectant composed of carboxybetaine represented by 1). 2. Carboxybetaine (1) is represented by the following formula: The moisturizing agent according to claim 1, which satisfies the above condition. 3. A cosmetic containing the carboxybetaine (1) according to claim 1. 4. A detergent composition containing the carboxybetaine (1) according to claim 1.