JP6462338B2 - Cosmetics containing amino sugar derivatives - Google Patents

Description

  The present invention relates to a cosmetic containing a specific amino sugar derivative, and shows an excellent moisturizing effect and feel improvement when blended in skin cosmetics, and when blended in hair cosmetics, It has a hair repairing effect to soften, has excellent moisture retention, and has an effect of improving touch.

  Hair is damaged by living environment such as ultraviolet rays and free chlorine, and human behavior such as hair care and hair makeup. In washing damaged hair, it is known that the surfactant, which is the main component of shampoo, elutes sebum and hair constituent proteins of the hair and weakens the hair.

  In recent years, the frequency of cold perms, hair coloring, hair bleaching, and the like has increased, and chemical treatment with chemicals has promoted elution and structural change of hair constituent proteins, which has spurred damage.

  Such weakened damaged hair and naturally thin and soft hair have a problem of difficulty in styling because there is no volume feeling.

  Styling is an especially important factor for hair makeup behavior for women, and cosmetics and makeup methods that give a sense of volume to hair have been developed and reported for a long time, but the effect has not been sufficient.

  On the other hand, the cosmetic use of amino sugars is disclosed in Patent Documents 1 to 3 regarding the use of alkylamino sugars and salts thereof. The substance should provide smoothness, moisturization, keratin softening effect and skin improvement effect to the skin, and it should give the hair a glossy, suppleness, a feeling of hair finish and improve combing. Is disclosed.

  The compounds carboxyalkylated to the nitrogen atom of the amino sugar are described in Patent Document 4 and Patent Document 5, but since the expression of foaming power and surface activity was sought, the nitrogen atom of the amino sugar simultaneously with the carboxyalkylation The substance group described in Patent Documents 4 to 5 exhibits the effect of the present invention, in which a hydrophobic group is provided with an alkyl group having 4 or more carbon atoms, an alkenyl group, an alkylphenyl group, or an acyl group. do not do.

JP 59-212419 A JP 59-212420 A JP 59-212421 A JP 05-117216 A JP 05-277351 A

  The problem to be solved by the present invention is to provide a cosmetic that has a hair repair effect that makes the hair thicker and softer when used in hair, is excellent in moisture retention, and has an effect of improving touch. is there.

  The present inventors have found that a cosmetic containing a specific amino sugar derivative has a hair repair effect that makes the hair thicker and softer. Furthermore, it has been found that the amino sugar derivative of the present invention has a moisturizing effect, and the cosmetic compounding this has excellent performance.

That is, the present invention
General formula (1)

[Wherein R ¹ is an alkyl group having 1 to 3 carbon atoms and a hydrogen atom, and when 1 is 2, R ¹ may be different from each other.

R ² is a hydrogen atom or a methyl group l is an integer from 1 to 2 m is an integer from 0 to 1 n is an integer from 1 to 2, l + n is an integer from 2 to 3, Y is 1 + n is 2 In this case, a nitrogen atom N is shown, and when l + n is 3, a quaternized nitrogen atom N ⁺ is shown.

The sugar residue is a reducing sugar having 4 to 6 carbon atoms, a disaccharide having a reducing end, an oligosaccharide, a group remaining after removing the glycosidic OH of the carbon bonded to Y from the condensate thereof X is a hydrogen atom or an alkali metal Represents. ]
It is related with the cosmetics containing the amine and / or quaternary nitrogen containing which are derived from the aminosaccharide shown by these.

  In particular, amines derived from aminosaccharides and / or quaternary nitrogen-containing compounds are represented by the general formula (2)

[Wherein R ³ is a hydrogen atom, p is an integer of 3 to 4 and others are the same as defined in the general formula (1)]
The present invention relates to a cosmetic containing a substance represented by

  The present invention relates to a cosmetic containing a specific amino sugar derivative, and shows an excellent moisturizing effect and feel improvement when blended in skin cosmetics, and when blended in hair cosmetics, It has a hair repairing effect to soften, has excellent moisture retention, and has an effect of improving touch.

1 is a ¹ H-NMR chart of a compound prepared in Production Example 1. FIG.

  Hereinafter, embodiments of the present invention will be described.

  The essential component in the cosmetic of the present invention is an amine and / or a quaternary nitrogen-containing substance derived from an amino sugar represented by the following general formula (1).

[Wherein R ¹ is an alkyl group having 1 to 3 carbon atoms and a hydrogen atom, and when 1 is 2, R ¹ may be different from each other.

R ² is a hydrogen atom or a methyl group l is an integer from 1 to 2 m is an integer from 0 to 1 n is an integer from 1 to 2, l + n is an integer from 2 to 3, Y is 1 + n is 2 In this case, a nitrogen atom N is shown, and when l + n is 3, a quaternized nitrogen atom N ⁺ is shown.

The sugar residue is a reducing sugar having C5-6, a disaccharide having a reducing end, an oligosaccharide, a group remaining after removing the glycosidic OH of the carbon condensed to Y from the condensate X represents a hydrogen atom or an alkali metal . ]
The important points of the amine and / or quaternary nitrogen-containing compound derived from the aminosaccharide represented by the general formula (1) are that it always has one or more carboxyalkyl groups and that the substituent represented by R ¹ is , A hydrogen atom or an alkyl group having 1 to 3 carbon atoms.

When there is no carboxyalkyl group, there is no ion binding site with hair, so only the same effect as in the prior art occurs. When R ¹ group is an alkyl group having 4 or more carbon atoms, water retention (moisturization) by hydrophobization There is a decrease in the sorption (affinity) to hair due to a decrease in property and an increase in molecular weight, and the effect of addition to cosmetics is lost. In addition, when the R ¹ group is an alkyl group having 4 or more carbon atoms, surface active ability is exhibited and foaming is observed, which may cause inconvenience when added to cosmetics.

  The amine derived from the aminosaccharide represented by the general formula (1) and / or the quaternary nitrogen-containing material may be blended individually or as a mixture. When blending a mixture, it may be blended after synthesis. In some cases, the reaction proceeds with a primary amine, secondary amine, tertiary amine, and quaternary nitrogen, so that a mixture can be formed during synthesis. The reaction molar ratio may be changed to synthesize a mixture, which may be blended.

  Amines derived from aminosaccharides represented by the general formula (1) and / or quaternary nitrogen-containing substances and mixtures thereof are carboxy-containing monohalocarboxylic acids such as monochloroacetic acid, acrylic acid, etc. with respect to amino sugars. It can be easily synthesized by reacting an alkylating agent and an alkylating agent comprising an alkyl halide (C1-C3) such as methyl iodide by a conventional method.

  The raw amino sugars include erythrosaminitol, threosaminitol, xylosaminitol, arabinosaminitol, liposaminitol, lyxosaminitol, abiosaminitol, glucosaminitol, galactosaminitol, mannosamini Toll, tarosaminitol, allosaminitol, altosaminitol, grosaminitol, idosaminitol, lactosaminitol and erythrosamine, threosamine, glucamine, arabinosamine, liposamine, lixosamine, abiosamine, galactamine, mannaamine, tarosamine, allosamin, altosamine, grosamine, grosamine Lactosamine, N-methyl-D-erythrosamine, N-ethyl-D-threosamine, N-propyl-D-arabinosamine, N-methyl-D-gluca Emissions, N- ethyl -D- glucamine, N- propyl -D- glucamine, N- ethyl -D- junk Min, N- methyl -D- Mantamin, N- propyl -D- Tarosamin the like.

  Among these amino sugars, N-methyl-D-glucamine, N-ethyl-D-glucamine, D-glucamine, N-methyl-D-mantamine, N-propyl-D- Glucamine is particularly preferred.

  In addition, amines derived from aminosaccharides represented by the general formula (1) and / or quaternary nitrogen-containing substances and mixtures thereof can also be synthesized from reducing sugars and amino acids by reductive amination reaction.

  Examples of the reducing sugar as a raw material include ribose, arabinose, xylose, lyxose, deoxyribose, allose, altrose, glucose, mannose, gulose, idose, galactose, talose and the like.

  Among these reducing sugars, glucose and mannose are particularly desirable in consideration of distribution / price and effects.

  Examples of the raw material amino acid include glycine, α-alanine, β-alanine, N-methylglycine, N-methyl β-alanine, and the like.

  Among these amino acids, glycine and β-alanine are particularly desirable in consideration of distribution / price and effects.

  An amine and / or quaternary nitrogen-containing substance derived from an aminosaccharide represented by the following general formula (2) is further included as an amine and / or quaternary nitrogen-containing substance derived from the aminosaccharide represented by the general formula (1). preferable.

[Wherein R ³ is a hydrogen atom, p is an integer of 3 to 4 and others are the same as defined in the general formula (1)]
The hair cosmetic composition of the present invention will be described.

  In the case of hair cosmetics, the hair repair effect, which is a feature of the present invention, can be expected, so that it is more preferable as an implementation of the present invention. Furthermore, the property of having a moisturizing property while having a hair repairing effect is an effect not found in other cosmetic raw materials. That is, the feature of the present invention is that it has both the effect of thickening hair and the effect of softening hair.

  In recent years, polyol and amino acid condensates and the like have been disclosed as repair agents, but none of these substances have a function of softening hair because of their low moisturizing properties.

  The hair cosmetic composition preferably contains 0.1% to 10.0% of an amine and / or quaternary nitrogen-containing compound derived from the amino sugar represented by the general formula (1) and a mixture thereof. .

  If the addition amount is less than 0.1%, the effect of increasing the volume of the hair is not recognized, and if the blending is more than 10.0%, the effect does not expand in proportion to the addition amount, and blending is possible, but the further effect is I can't hope. Further, when the amount is more than 10.0%, stickiness is felt during use, and the touch is not good.

  Specific examples of hair cosmetics include hair brushing agent compositions, hair treatment compositions, hair rinse compositions, hair shampoo compositions, hair essence compositions, and the like.

  The skin cosmetic of the present invention will be described.

  In the case of skin cosmetics, it becomes the thing using the moisture retention of the amine and / or quaternary nitrogen containing substance derived from the aminosaccharide shown by General formula (1), and these mixtures.

  The skin cosmetic composition preferably contains 0.1% to 10.0% of an amine and / or quaternary nitrogen-containing substance derived from the amino sugar represented by the general formula (1) and a mixture thereof. .

  When the addition amount is less than 0.1%, the moisturizing effect is not sufficiently observed, and when the blending amount is more than 10.0%, the effect does not expand in proportion to the addition amount, and blending is possible, but no further effect can be expected. . Further, when the amount is more than 10.0%, stickiness is felt during use, and the touch is not good.

  Specific examples of hair cosmetics include emulsions, lotions and creams.

  In the cosmetics of the present invention, animals, plants, fish shellfish, microorganism-derived extracts, powder components, liquid fats and oils, solid fats and oils, waxes, hydrocarbons, higher fatty acids, higher alcohols and esters, as long as the effects are not impaired. , Silicone, anionic surfactant, cationic surfactant, amphoteric surfactant, nonionic surfactant, moisturizer, water-soluble polymer, thickener, coating agent, ultraviolet absorber, flame retardant, metal sequestering agent, Lower alcohols, sugars other than the general formula (1) of the present invention, amino acids, organic amines, synthetic resin emulsions, pH adjusters, skin nutrients, vitamins, antioxidants, antioxidant aids, fragrances and deep ocean water 1 type or 2 types or more may be used as needed.

  Hereafter, it is an essential component of this invention by a test example and a comparative test example. The usefulness of amines and / or quaternary nitrogen-containing substances derived from aminosaccharides represented by the general formula (1) will be shown, and the present invention will be described in more detail by way of examples. It is not limited to.

  By the methods of Production Examples 1 to 11, amines and / or quaternary nitrogen-containing substances derived from aminosaccharides represented by the general formula (1) were synthesized. The performance of the substances obtained in Production Examples 1 to 11 as cosmetic raw materials was carried out in Test Examples 1 to 11, and N-propyl-D-glucamine, which is a synthetic intermediate of Production Example 9, and Tokyo Chemical Industry as a comparative test example. D-glucamine, N-methyl-D-glucamine, and N-ethyl-D-glucamine were added and the various tests shown in Table 1 were carried out and shown in Comparative Test Examples 1 to 4. The results of test examples and comparative test examples are summarized in Table 1.

  It was confirmed that amines and / or quaternary nitrogen-containing substances derived from aminosaccharides represented by the general formula (1) are useful cosmetic raw materials.

Production Example 1
In a 300 ml four-necked flask, 20 g of N-methyl-D-glucamine (Tokyo Kasei) was added and dissolved by adding 100 g of distilled water. 10.3 g (1 equivalent) of ethyl acrylate was added dropwise, heated to 60 ° C. and stirred for 3 hours. The ester is hydrolyzed by adding 48% NaOH dropwise, and the ester is hydrolyzed. After cooling to room temperature, neutralization with hydrochloric acid, acetone and ethanol are added to precipitate the target product, and the by-product NaCl is removed by filtration and washing. As a result, 28 g of a white powdery target product was obtained. The structure of the target product was confirmed by ¹ H-NMR. ¹ H-NMR measurement and analysis results are shown in FIG.
It can be seen that N-methyl-N-carboxyethylglucamine has been synthesized.

Production Example 2
In a 300 ml four-necked flask, 20 g of N-methyl-D-glucamine (Tokyo Kasei) was added and dissolved by adding 100 g of distilled water. A 50% aqueous monochloroacetic acid solution (pure 9.7 g, 1 equivalent) and a 24% aqueous NaOH solution were added dropwise so that the pH was 8-9, and the mixture was heated to 60 ° C. and stirred for 7 hours. After allowing to cool to room temperature, acetone and ethanol were added to precipitate the target product, which was then filtered and washed to remove by-produced NaCl, thereby obtaining 25 g of a white powdery target product. The structure of the target product was confirmed by ¹ H-NMR.

Production Example 3
In a 300 ml four-necked flask, 20 g of the compound of Production Example 1 was added, and 100 g of distilled water was added and dissolved. 9.8 g (1 equivalent) of methyl iodide was added dropwise, and the mixture was stirred at room temperature for 4 hours. Lyophilization gave 29 g of the white powdery target product. The structure of the target product was confirmed by ¹ H-NMR.

Production Example 4
In a 300 ml four-necked flask, 20 g of the compound of Production Example 2 was added, and 100 g of distilled water was added and dissolved. Methyl iodide (10.3 g, 1 equivalent) was added dropwise, and the mixture was stirred at room temperature for 4 hours. Lyophilization gave 29 g of the white powdery target product. The structure of the target product was confirmed by ¹ H-NMR.

Production Example 5
In a 300 ml four-necked flask, 20 g of N-ethyl-D-glucamine (Tokyo Kasei) was added and dissolved by adding 100 g of distilled water. A 50% aqueous monochloroacetic acid solution (pure content: 9.0 g, 1 equivalent) and a 24% aqueous NaOH solution were added dropwise so that the pH was 8 to 9, and the mixture was heated to 60 ° C. and stirred for 7 hours. After allowing to cool to room temperature, acetone and ethanol were added to precipitate the target product, and by-product NaCl was removed by filtration and washing to obtain 24 g of a white powdery target product. The structure of the target product was confirmed by ¹ H-NMR.

Production Example 6
In a 300 ml four-necked flask, 20 g of D-glucamine (Tokyo Kasei) was added and dissolved by adding 100 g of distilled water. 11.0 g (1 equivalent) of ethyl acrylate was added dropwise, heated to 60 ° C. and stirred for 3 hours. The ester is hydrolyzed by adding 48% NaOH dropwise, and the ester is hydrolyzed. After cooling to room temperature, neutralization with hydrochloric acid, acetone and ethanol are added to precipitate the target product, and the by-product NaCl is removed by filtration and washing. As a result, 28 g of a white powdery target product was obtained. The structure of the target product was confirmed by ¹ H-NMR.

Production Example 7
In a 300 ml four-necked flask, 20 g of N-methyl-D-glucamine (Tokyo Kasei) was added and dissolved by adding 100 g of distilled water. A 50% aqueous monochloroacetic acid solution (pure 19.4 g, 2 equivalents) and a 24% aqueous NaOH solution were added dropwise so that the pH was 8-9, and the mixture was heated to 60 ° C. and stirred for 7 hours. After allowing to cool to room temperature, acetone and ethanol were added to precipitate the target product, and by-product NaCl was removed by filtration and washing to obtain 33 g of a white powdery target product. The structure of the target product was confirmed by ¹ H-NMR.

Production Example 8
A 500 mL autoclave was charged with 36 g of anhydrous maltose, 53 mL (1 equivalent) of a 2M methanol solution of methylamine, 200 mL of methanol, 1 g (dry weight) of palladium carbon catalyst (Kawaken Fine Chemical), and stirred at 60 ° C. and a hydrogen pressure of 5 MPa for 6 hours. When the theoretical amount of hydrogen is absorbed, it is cooled to room temperature, hydrogen is blown, the catalyst is filtered from the reaction solution, methanol is distilled off from the filtrate under reduced pressure, and a slightly yellow solid of N-methyl-D-mantamine is obtained. 35 g of was obtained.
In a 300 ml four-necked flask, 20 g of N-methyl-D-mantamine was added, and 100 g of distilled water was added and dissolved. A 50% aqueous monochloroacetic acid solution (pure content 5.3 g, 1 equivalent) and a 24% aqueous NaOH solution were added dropwise so that the pH was 8-9, and the mixture was heated to 60 ° C. and stirred overnight. After allowing to cool to room temperature, acetone and ethanol were added to precipitate the target product, and by-product NaCl was removed by filtration and washing to obtain 22 g of a white powdery target product. The structure of the target product was confirmed by ¹ H-NMR.

Production Example 9
A 500 mL autoclave was charged with 36 g of anhydrous glucose, 11.8 g (1 equivalent) of n-propylamine, 250 mL of methanol, 1 g (dry weight) of 5% palladium carbon catalyst (Kawaken Fine Chemical), and stirred at 60 ° C. and a hydrogen pressure of 5 MPa for 5 hours. When the theoretical amount of hydrogen is absorbed, it is cooled to room temperature, blown with hydrogen, the catalyst is filtered from the reaction solution, methanol is distilled off from the filtrate under reduced pressure, and a white solid of N-propyl-D-glucamine is obtained. 40 g was obtained.
In a 300 ml four-necked flask, 20 g of N-propyl-D-glucamine was added, and 100 g of distilled water was added and dissolved. A 50% aqueous monochloroacetic acid solution (pure content 8.5 g, 1 equivalent) and a 24% aqueous NaOH solution were added dropwise so that the pH was 8-9, and the mixture was heated to 60 ° C. and stirred for 8 hours. After allowing to cool to room temperature, acetone and ethanol were added to precipitate the target product, and by-product NaCl was removed by filtration and washing to obtain 23 g of a white powdery target product. The structure of the target product was confirmed by ¹ H-NMR.

Production Example 10
In a 300 ml four-necked flask, 20 g of N-methyl-D-glucamine (Tokyo Kasei) was added and dissolved by adding 100 g of distilled water. Methyl methacrylate (10.3 g, 1 equivalent) was added dropwise, heated to 60 ° C. and stirred for 5 hours. The ester is hydrolyzed by adding 48% NaOH dropwise, and the ester is hydrolyzed. After cooling to room temperature, neutralization with hydrochloric acid, acetone and ethanol are added to precipitate the target product, and the by-product NaCl is removed by filtration and washing. As a result, 26 g of a white powdery target product was obtained. The structure of the target product was confirmed by ¹ H-NMR.

Production Example 11
A 500 mL autoclave was charged with 54.1 g of anhydrous glucose, 26.7 g of β-alanine (1 equivalent), 120 g of distilled water, 1.8 g (dry weight) of 5% palladium carbon catalyst (Kawaken Fine Chemical), 60 ° C., hydrogen pressure 5 MPa. For 10 hours, when the theoretical amount of hydrogen was absorbed, cooled to room temperature, blown hydrogen, filtered the catalyst from the reaction solution, and then added acetone and ethanol to precipitate the target product. 42 g of product was obtained. The structure of the target product was confirmed by ¹ H-NMR.

Description of test method Measurement of hair thickness change rate Six straight hairs were selected from a bleached hair bundle (Buelux, BR-3-A) and fixed on an electron microscope measurement stage. Twelve places were measured and set as the initial hair diameter. Immerse the hair in a 1% aqueous solution of the compound of the production example (pH 5.0, prepared with citric acid or NaOH) at 40 ° C. for 10 minutes at the measurement stage, rinse with distilled water, dry with a dryer, and measure the initial hair diameter. The same twelve locations were measured, the thickness change rate was calculated, and the average value is shown in Table 1. As a calculation example, in the case of the compound of Production Example 1, the initial hair diameter is 86 μm, the hair diameter after immersion is 103 μm, and the change rate of the hair thickness is 103 ÷ 86 × 100 = 120%. The larger the value, the thicker the hair.
<Evaluation criteria for rate of change of hair thickness>
○: 110% or more △: 105% or more and 109% or less ×: Less than 105%

2. Measuring the rate of change in the softness of hair Select 50 straight hairs from a bleached hair bundle (Buelux, BR-3-A) and place them in parallel at 1 mm intervals, with a measurement site of 2 cm, and a transparent plastic thin plate on both sides Fixed with tape. The sample was left standing overnight in a constant temperature and humidity room at room temperature of 20 ° C. and humidity of 60%, and was subjected to stress [B value (gf · cm ² / g / f) by a pure bending tester (KESFB2-S type, manufactured by Kato Tech Co., Ltd.). cm)]. This B value is a numerical value indicating bending elasticity when one of the hairs is fixed and bent at a constant speed, and the smaller the numerical value, the softer the hair. The B value of bleached hair is 0.257 gf · cm ² / cm, 0.223 for black hair (Buelux, BS-B), and it is quantified that bleaching healthy hair (black hair) results in hard hair. It was done.
A sample for measurement of bleached hair bundles is immersed in a 1% aqueous solution of the compound of the preparation example (pH 5.0, prepared with citric acid or NaOH) at 40 ° C. for 10 minutes, rinsed with distilled water, dried with a dryer, and room temperature 20 ° C. The sample was allowed to stand overnight in a constant temperature and humidity chamber with a humidity of 60%, the B value was measured, and the rate of change in the softness of the hair was calculated. As a calculation example, in the case of the compound of Production Example 1, the B value after immersion is 0 · 193 gf · cm ² / cm, and the change rate of the softness of the hair is 0.257 ÷ 0 · 193 × 100 = 133%. The higher the value, the softer the hair.
<Evaluation criteria for rate of change of hair softness>
○: 116% or more △: 107% or more and 115% or less ×: Less than 106%

3. Measurement of sorption amount on hair Weight: 1 g of bleached hair bundle (Buelux, BR-3-A) 20 g of 5% aqueous solution of the compound of the preparation example (prepared with 1 g of pure component, pH 5.0, citric acid or NaOH) For 30 minutes at 40 ° C. The hair bundle was removed, and the amount of sorption on the hair was calculated from the evaporation residue of the aqueous solution. As a calculation example, in the case of the compound of Production Example 1, the evaporation residue of the aqueous solution is 0.79 g, and the sorption amount to the hair is (1−0.79) ÷ 1 × 100 = 21%. It shows that there is so much sorption amount to hair that a numerical value is large.
<Evaluation criteria for sorption amount on hair>
○: 15% or more △: 5% or more and 14% or less ×: Less than 5%

4). Measurement of water retention of hair Weight 1 g of bleached hair bundle (Buelux, BR-3-A) to 100 g of 5% aqueous solution of the compound of preparation example (pH 5.0, prepared with citric acid or NaOH) at 40 ° C. Soaked for hours. Rinse the hair bundle with distilled water, dry it with a dryer, leave it overnight in a constant temperature and humidity chamber at room temperature of 20 ° C and 60% humidity, and dry it in a thermostatic chamber at 130 ° C for 30 minutes to measure the weight of the hair bundle. The water retention was calculated. As a calculation example, in the case of the compound of Production Example 1, the weight of the hair bundle after drying is 0.94 g, and the water retention of the hair is 0.94 ÷ 1 × 100 = 94%. It shows that the water retention of hair is so high that a numerical value is large.
<Evaluation criteria for water retention of hair>
○: 92% or more △: 88% or more and 91% or less ×: Less than 88%

5. Moisture absorption and retention test 300 mg of the dry powder of the compound of Production Example was allowed to stand at 20 ° C. for 7 days in a desiccator with a humidity of 80%, and the weight was measured. Subsequently, it was left still at 20 ° C. with a desiccator having a humidity of 33%, and the weight was measured. As a calculation example, in the case of the compound of Production Example 1, the weight after storage at 80% humidity is 510 mg, the weight after storage at 33% humidity is 348 mg,
The water absorption is (510−300) ÷ 300 × 100 = 70%,
The water retention rate is (348−300) ÷ 300 × 100 = 16%, and the larger the value, the higher the water absorption rate and the water retention rate.
<Evaluation criteria for water absorption>
○: 65% or more Δ: 50% or more and 64% or less ×: Less than 50% <Evaluation criteria for water retention>
○: 10% or more △: 5% or more and 9% or less ×: Less than 5%

  Below are the structures of the compounds synthesized in the test examples and comparative test examples, and the measurement values of the change rate of the thickness of the hair, the change rate of the softness, the amount of sorption to the hair, the water retention property of the hair, and the moisture absorption and retention property. The evaluation results are shown in Table 1. In addition, the rate of change in the thickness of the hair, the rate of change in softness, the amount of sorption on the hair, the water retention and moisture absorption evaluation results are shown in the upper part of each column, and the measured values are shown in the lower part of each column. Show.

  All of Test Examples 1 to 11 in the present invention are compounds that have a good rate of change in the thickness of the hair and increase the volume of the hair. All of Test Examples 1 to 11 are compounds that have a good rate of change in the softness of the hair and make the hair soft and supple. Each of Test Examples 1 to 11 is a compound that has an excellent sorption amount on hair and is easily compatible with hair. Each of Test Examples 1 to 11 is a compound having good water retention and moisture absorption and moisture retention, and excellent moisture retention and moist feeling. On the other hand, all of Comparative Test Examples 1 to 4 having no carboxylic acid were not good in the change rate of the thickness of the hair, the change rate of the softness, the sorption amount to the hair, the water retention property and the moisture retention property. It was.

  All show that amines derived from aminosaccharides represented by the general formula (1) and / or quaternary nitrogen-containing substances are excellent cosmetic raw materials.

  The cosmetics which mix | blended the amine and / or quaternary nitrogen containing material derived from the aminosaccharide shown by General formula (1) below, and these mixtures were mix | blended, and the outstanding effect was confirmed.

Example 1
When the hair brushing agent composition shown below was prepared and its performance was evaluated, this hair brushing agent composition showed high moisturizing properties, and the user felt excellent moist feeling, hair volume up feeling, hair softness. I could feel it. The numbers in the composition indicate mass%.
(composition)
Cocoyl arginine ethyl ester / PCA salt 0.5
Compound obtained in Production Example 1 0.5
Ethanol 5.0
Methylparaben 0.1
Fragrance 0.1
Purified water balance (prepared so that the total is 100)

Example 2
The hair treatment composition shown below was prepared and its performance was evaluated. This hair treatment composition showed high moisture retention, and the user felt excellent moist feeling, increased hair volume, and softness of the hair. I was able to.
(composition)
PPG-1 / PEG-1 stearamine 3.0
Compound obtained in Production Example 2 0.3
Cetostearyl alcohol 2.5
Liquid paraffin 1.5
POE (5) stearyl ether 1.0
Glycerin 5.0
Preservative 0.1
Purified water balance (prepared so that the total is 100)

Example 3
When the emulsion shown below was prepared and the performance was evaluated, this emulsion showed high moisturizing properties and the user could feel an excellent moist feeling.
(composition)
Liquid paraffin 10.0
Squalane 2.0
Vaseline 2.0
Sorbitan sesquioleate 0.9
Polyoxyethylene oleyl ether 1.2
Glycerin 3.0
Ethanol 3.0
Carboxyvinyl polymer 0.2
Potassium hydroxide 0.1
Compound obtained in Production Example 3 0.2
PCA soda 1.0
Loofah extract 1.0
Preservative 0.5
Purified water balance (prepared so that the total is 100)

Example 4
When the hair rinse composition shown below was prepared and its performance was evaluated, this hair rinse composition showed high moisture retention, and the user felt excellent moist feeling, hair volume up feeling, and hair softness. I was able to.
(composition)
PPG-1 / PEG-1 stearamine 3.0
Cetanol 3.5
Jojoba oil 2.0
Lipophilic glyceryl monostearate 1.0
Polyethylene glycol (8EO) 0.3
1.3-Butylene glycol 5.0
Compound 1.0 obtained in Production Example 4
Hyaluronic acid 0.2
Amino-modified silicone polymer 0.5
Preservative 0.3
Purified water balance (prepared so that the total is 100)

Example 5
The hair shampoo composition shown below was prepared and its performance was evaluated. The hair shampoo composition showed high moisture retention, and the user felt excellent moist feeling, hair volume up, and softness of the hair. I was able to.
(composition)
Polyoxyethylene (3) sodium lauryl ether sulfate (25%) 10.0
Lauroylmethyl-β-alanine sodium (30%) 15.0
Hydroxyalkyl (C12-14)
Hydroxyethyl sarcosine (27%) 15.0
N-cocoyl-L-glutamic acid monotriethanol amine salt (30%) 10.0
Lauric acid diethanolamide 3.0
Compound 1.0 obtained in Production Example 5
Sodium edetate 0.2
Preservative 0.3
Purified water balance (prepared so that the total is 100)

Example 6
When the lotion composition shown below was prepared and the performance was evaluated, this lotion showed high moisturizing properties and the user could feel an excellent moist feeling.
(composition)
Ethanol 10.0
Glycerin 5.0
Compound obtained in Production Example 6 5.0
Methylparaben 0.1
Sodium edetate 0.1
Purified water balance (prepared so that the total is 100)

Example 7
When the hair essence composition shown below was prepared and its performance was evaluated, this hair essence showed high moisturizing properties, and the user might feel excellent moist feeling, hair volume up, and hair softness. did it.
(composition)
Ethanol 20.0
Compound obtained in Production Example 7 0.3
Methylparaben 0.1
Sodium edetate 0.1
Purified water balance (prepared so that the total is 100)

Example 8
When the lotion composition shown below was prepared and the performance was evaluated, this lotion showed high moisturizing properties and the user could feel an excellent moist feeling.
(composition)
Compound obtained in Production Example 8 1.8
Sorbit liquid 2.0
Polyoxyethylene sorbitan monooleate 0.5
Ethanol 5.0
Methyl paraoxybenzoate 0.2 Purified water The remainder (prepared so that the total is 100)

Example 9
When the following O / W type cream was prepared and its performance was evaluated, this O / W type cream showed high moisturizing properties and the user could feel an excellent moist feeling.
(composition)
Olive oil 9.0
Paraffin 3.0
Isopropyl myristate 2.5
Lanolin 3.5
Beeswax 2.0
Cetanol 5.5
Tetraoleic acid polyoxyethylene sorbit (40 mol) 2.0
Tetraoleic acid polyoxyethylene sorbit (60 mol) 2.0
Propyl paraoxybenzoate 0.1
Ethyl paraoxybenzoate 0.1
Propylene glycol 9.0
Fragrance 0.2
Compound obtained in Production Example 9 0.6
Purified water balance (prepared so that the total is 100)

Example 10
When the emulsion shown below was prepared and the performance was evaluated, this emulsion showed high moisturizing properties and the user could feel an excellent moist feeling.
(composition)
Isopropyl myristate 3.5
Lanolin 2.0
Olive oil 1.5
Cetanol 2.0
Squalane 0.5
Tetraoleic acid polyoxyethylene sorbit (40 mol) 2.0
Tetraoleic acid polyoxyethylene sorbit (60 mol) 2.0
Propyl paraoxybenzoate 0.1
Ethyl paraoxybenzoate 0.1
Propylene glycol 9.0
Compound obtained in Production Example 10 0.8
Purified water balance (prepared so that the total is 100)

Example 11
The hair shampoo composition shown below was prepared and its performance was evaluated. The hair shampoo composition showed high moisture retention, and the user felt excellent moist feeling, hair volume up, and softness of the hair. I was able to.
(composition)
Compound obtained in Production Example 11 0.5
Sodium lauryl ether (2EO) sulfate 6.0
Sodium lauryl sulfate 3.5
Palm oil fatty acid diethanolamide 4.5
Propylene glycol 2.0
Edetic acid 0.2
Purified water balance (prepared so that the total is 100)

Example 12
The hair shampoo composition shown below was prepared and its performance was evaluated. The hair shampoo composition showed high moisture retention, and the user felt excellent moist feeling, hair volume up, and softness of the hair. I was able to.
(composition)
Hydroxyalkyl (C12-14)
Hydroxyethyl sarcosine (27%) 30.0
Lauroylmethyl-β-alanine sodium (30%) 15.0
Coconut oil fatty acid diethanolamide 3.0
Compound obtained in Production Example 1 1.0
Compound 1.0 obtained in Production Example 2
Polyquaternium-10 0.2
Preservative 0.3
Purified water balance (prepared so that the total is 100)

  The present invention shows an excellent moisturizing effect and feel improvement when blended with a specific amino sugar derivative in skin cosmetics, and has a hair repair effect that thickens and softens hair when blended into hair cosmetics. It is also useful as a cosmetic because it has excellent moisturizing properties and improves the feel.

Claims (5)

General formula (1)
[Wherein R ¹ is an alkyl group having 1 to 3 carbon atoms and a hydrogen atom, and when 1 is 2, R ¹ may be different from each other.
R ² is a hydrogen atom or a methyl group l is an integer from 1 to 2 m is an integer from 0 to 1 n is an integer from 1 to 2, l + n is an integer from 2 to 3, Y is 1 + n is 2 In this case, a nitrogen atom N is shown, and when l + n is 3, a quaternized nitrogen atom N ⁺ is shown.
The sugar residue is a reducing sugar having 4 to 6 carbon atoms, a disaccharide having a reducing end, an oligosaccharide, a group remaining after removing the glycosidic OH of the carbon bonded to Y from the condensate thereof X is a hydrogen atom or an alkali metal Represents. ]
In the indicated Rua Min and / or quaternary nitrogen-containing substance a cosmetic for hair repair containing 0.2 to 10.0 wt%. A Min and / or quaternary nitrogen-containing compound is represented by the general formula (2)
[Wherein R ³ is a hydrogen atom, p is an integer of 3 to 4 and others are the same as defined in the general formula (1)]
The cosmetic according to claim 1, which is a compound represented by the formula: Comprising the amine and / or quaternary nitrogen-containing compound represented by the general formula (1), induced by reductive amination of a reducing sugar and amino acids, the production of cosmetic according to claim 1 or 2 Method. Wherein the reducing sugar is ribose, arabinose, xylose, lyxose, deoxyribose, allose, altrose, glucose, mannose, gulose, idose, to claim 3 is at least one reducing sugar selected from the group consisting of galactose and talose The manufacturing method of cosmetics as described . The cosmetic preparation according to claim 3 or 4 , wherein the amino acid is at least one amino acid selected from the group consisting of glycine, α-alanine, β-alanine, N-methylglycine and N-methyl β-alanine. Method.