KR20000046973A - Cosmetic composition comprising polyethoxylated letineamide derivatives - Google Patents

Abstract

PURPOSE: A cosmetic composition comprising polyethoxylated letineamide derivatives is provided for inhibiting aging of the skin. CONSTITUTION: A cosmetic composition comprises polyethoxylated letineamide derivatives of the following formula I in the range from 0.001 to 50 wt %, preferably 0.01 to 20 wt %, wherein R is hydrogen or C1-6 alkyl group, and n is an integer of 2 to 100; anti-oxidant agents selected from the group consisting of water-soluble Kosan Hongkyungchun extract, nordihydroguaiaretic acid, fat-soluble tocopherol, tocopherol acetate, butylhydroxytoluene, and butylhydroxyanisole in the range from 0.01 to 5 wt %; divalent ionic metal salts selected from the group consisting of magnesium hydrogen sulfate, magnesium stearic acid, magnesium acetylsalicylic acid, calcium acetylsalicylic acid, calcium hydroxide, barium hydrogen sulfate, zinc hydrogen sulfate, strontium chloride, and strontium bromide in the range from 0.001 to 5 wt %.

Description

Anti-aging cosmetic composition containing polyethoxylated retinamide

The present invention relates to an anti-aging cosmetic composition containing a polyethoxylated retinamide derivative of the following general formula (1). More specifically, the present invention uses the 13-trans-polyethoxylated retinamide derivative of Formula 1, which is an anti-aging raw material having excellent collagen synthesis and cell regeneration effect, with an antioxidant and a divalent metal salt to prevent photoaging and wrinkle improvement. It relates to an anti-aging cosmetic composition further enhanced the anti-aging effect.

Where

R is hydrogen or a C _1-6 alkyl group,

n is a number from 2 to 100.

Wrinkle prevention is one of the important functions of cosmetics has been a lot of research in the past for this purpose. For example, application of cosmetics containing tretinoin (all-trans-retinoic acid) may improve photoaging of the skin (see Webb et al., "Topical Tretinoin Improves Photoaged Skin", JAMA, 259, vol 4, pp 95, 527-532, Jan, 22/29, 1988). However, while the cosmetics have a photoaging effect, they cause side effects such as skin dryness, wounds, peeling off during periods of irritation of the skin due to the properties of tretinoin, that is, low absorption by fat solubility, instability, and incubation periods. Because of these side effects, there are many difficulties in using tretinoin as a main ingredient of cosmetics. Therefore, there is an urgent need for development of anti-aging cosmetics having a new function, which is essentially non-irritating for suppressing photoaging while maintaining tretinoin activity as a skin treatment.

In addition, it is known that an ester or amide derivative of 13-trans retinoic acid has an anti-aging function such as treating skin diseases and acne. For example, the use of a compound of 2- (all-trans-retinoyloxy) -4-methoxy acetophenone has been reported to be relatively non-irritating and effective in inhibiting skin cancer or photoaging (see US Pat. No. 4,677,120). Compounds obtained by esterification of retinoic acid with tetraethylene glycol are known to increase the penetration effect of the skin (see US Pat. No. 4,900,478). Meanwhile, N- (4-hydroxyphenyl) retinamide (4-HPR) and retinoyl β-gluronide (RAG) have also been reported to have decreased relative toxicity while retaining the activity of conventional retinoic acid (FASEB J). , 10,1014-1024,1996).

However, the above-mentioned esters and amides of retinoic acid have insufficient skin absorption due to the fat-soluble properties, so it is difficult to expect the enhanced function of collagen synthesis and the anti-elastin degradation effect, and the stability against light, temperature and oxygen is poor, and the biological There is a problem of stability due to rapid enzymatic degradation in the interior. Therefore, even though the irritant, which is a disadvantage in using conventional retinoic acid derivative anti-aging cosmetics, has been somewhat overcome, there is still a need for an anti-aging agent for maximizing cell regeneration in vivo and improving preservation stability. I would say.

Therefore, the present inventors conducted an intensive study to solve the conventional problems, and in the process, the polyethoxylated retinamide derivatives are soluble in water or oil, have high skin absorption, and have excellent stability in vivo. Considering that there was an attempt to apply it to the anti-aging cosmetics. The cosmetic composition developed as described above has excellent stability and skin absorption ability compared to the existing skin anti-aging cosmetic composition, and showed an excellent effect in preventing skin aging.

Figure 1 shows the surface tension lowering ability of the polyethoxylated retinamide derivative (R: methyl, n: 10.7) of formula (1).

2 shows the interfacial tension-lowering ability of the polyethoxylated retinamide derivative (R: methyl, n: 10.7) of formula (1).

FIG. 3 shows a water layer, an emulsified layer and an oil layer in which the polyethoxylated retinamide derivative (R: methyl, n: 10.7) of Chemical Formula 1 is dispersed in Experimental Example 2. FIG.

The present invention relates to a skin anti-aging cosmetic composition containing a polyethoxylated retinamide derivative of the general formula (1):

Where

R is hydrogen or a C _1-6 alkyl group,

n is a number from 2 to 100.

The polyethoxylated retinamide derivatives of the general formula (1) have surface-active properties, so they are oriented at the interface between water, oil, and water and oil, and show a difference in storage stability depending on the orientation position. In particular, the storage stability was higher when oriented to the interface or oil side than in water, which is thought to be due to dissolved oxygen in water. In view of these characteristics, the present inventors solved the oxidation stability by dissolved oxygen by using a water-soluble antioxidant instead of an oil-soluble antioxidant for oil oxidation, which was previously used as an antioxidant, and using a divalent metal salt. The polyethoxylated retinamide derivative of was orientated to the oil or the interface of water and oil as much as possible to further increase the storage stability. Therefore, the present invention further contains a water-soluble antioxidant and a divalent metal salt.

The composition of the present invention contains 0.001 to 50% by weight, preferably 0.01 to 20% by weight of the polyethoxylated retinamide derivative of formula (1). If the amount of use is less than 0.001% by weight, it is difficult to expect a substantial effect. If the amount is more than 50% by weight, the formulation and product stability are affected.

In the present invention, one paper is selected from the group consisting of water-soluble high-acid rhodiola sac extract, nordihydroguaiaretic adid, oil-soluble tocopherol, tocopheryl acetate, butylhydroxytoluene and butylhydroxyanisole as antioxidants. 0.01 to 5% by weight. If the amount is less than 0.01% by weight, there is no antioxidant effect. If the amount is more than 5% by weight, there is no apparent increase in effect due to the increase in content.

The divalent metal salt contains 0.001 to 5% by weight of one or more selected from the group consisting of magnesium sulfate, magnesium stearate, magnesium acetylsalicylate, calcium acetylsalicylate, calcium hydroxide, barium sulfate, zinc sulfate, strontium chloride and strontium bromide. If the amount is less than 0.001% by weight, there is no antioxidant effect. If the amount is more than 5% by weight, there is no apparent increase in effect due to the increase in content.

When antioxidants, divalent metal salts and polyethoxylated retinamide derivatives of formula (1) are used in the amounts mentioned above, the stability of the raw materials and products is maximized.

The composition according to the present invention can be prepared according to a conventional method, such as skin external ointment, softening longevity, nutrient fluid, nutrition cream, massage cream pack or essence.

Hereinafter, the present invention will be described in detail with reference to Examples, but these Examples do not limit the technical scope of the present invention.

Example 1

Skin Ointment

A skin external ointment having the following composition was prepared according to a conventional method.

weight%

Polyethoxylated Retinamide Derivatives (R: Methyl, n: 10.7) 15.0

Diethyl Sebacate 8.0

Low payment 5.0

Polyoxyethylene Oleyl-Ether Phosphate (EO 4) 6.0

Paraoxybenzoic acid ester appropriate amount

Remaining amount of vaseline

Total 100

Example 2

Flexible Cosmetics

According to a conventional method, a flexible cosmetic having the following composition was prepared.

weight%

Polyethoxylated Retinamide Derivatives (R: Methyl, n: 10.7) 3.0

Glycerin 2.0

Hyaluronic Acid 1.0

Polyoxyethylene Oleyl Ether (EO20) 0.1

Polyoxyethylene Cured Castor Oil (EO40) 0.1

Paraoxybenzoic acid ester appropriate amount

Spices

Pigment amount

Purified water level

Total 100

Example 3

essence

According to the conventional method, an essence having the following composition was prepared.

weight%

Polyethoxylated Retinamide Derivatives (R: Methyl, n: 10.7) 12.0

Concentrated glycerin 10.0

Propylene Glycol 10.0

Polyoxyethylene Cured Castor Oil (EO40) 1.0

Ethanol 5.0

Paraoxybenzoic acid ester appropriate amount

Spices

Purified water level

Total 100

Example 4

Nutrition

According to the conventional method, a nutrient emulsion having the following composition was prepared.

weight%

Polyethoxylated Retinamide Derivatives (R: Methyl, n: 10.7) 1.0

Cetanol 1.0

Beeswax 0.5

Vaseline 2.0

Squalane 6.0

Ethanol 3.0

1,3-butylene glycol 4.0

Polysorbate 60 1.0

Solbitan Sesqui Olate 0.3

Carboxy Vinyl Polymer 0.3

Triethanolamine 0.3

Paraoxybenzoic acid ester appropriate amount

Spices

Pigment amount

Purified water level

Total 100

Example 5

Nutrition Cream

According to the conventional method, a nourishing cream having the following composition was prepared.

weight%

Polyethoxylated Retinamide Derivatives (R: Methyl, n: 10.7) 20.0

Stearyl Alcohol 6.0

Stearic Acid 2.0

Concentrated glycerin 1.0

Squalane 9.0

1,3-butylene glycol 6.0

Polysorbate 60 1.5

Polyethylene Glycol 1000 4.0

Cured Lanolin 4.0

Octyl Dodecanol 10.0

Sorbitan Stearate 0.8

Triethanolamine 0.5

Paraoxybenzoic acid ester appropriate amount

Spices

Pigment amount

Purified water level

Total 100

Comparative Example 1 and Examples 6 to 8

Essences were prepared according to conventional methods using the ingredients listed in Table 1 below.

essence Raw material name Comparative Example 1 Example 6 Example 7 Example 8 Cyclomethicone 15.0 15.0 15.0 15.0 Caprylic Capric Triglyceride 3.0 3.0 3.0 3.0 Mineral oil 3.0 3.0 3.0 3.0 Beeswax 1.0 1.0 1.0 1.0 Tocopherol - 1.0 1.0 1.0 Cetyl Dimethicone Copolyol 3.0 3.0 3.0 3.0 Polyethoxylated retinamide derivatives (R: methyl, n: 10.7) 5.0 5.0 5.0 5.0 glycerin 5.0 5.0 5.0 5.0 Alpine Honggyeongcheon Extract - - 3.0 3.0 Magnesium sulfate - - - 3.0 Paraoxybenzoic Acid Ester Quantity Quantity Quantity Quantity Purified water Remaining amount Remaining amount Remaining amount Remaining amount

(weight%)

Experiment 1: Surfactability Test of Polyethoxylated Retinamide Derivatives of Formula 1 (R: Methyl, n: 10.7)

The interfacial tension, i.e., surface tension, of the aqueous solution with air was measured in the aqueous solution state to test the interfacial capacity of the polyethoxylated retinamide derivative of Formula 1 wherein R is methyl and n was 10.7. The measurement was performed after leaving an aqueous solution in a concentration range of 10 ^-7 mol to 10 ^-2 mol of the polyethoxylated retinamide derivative of Chemical Formula 1 in a cool dark place for 24 hours to maintain the equilibrium and then measure the change in surface tension. The instrument used Krus's K12 Tensiometer, and the measurement method was De Nuoy's cyclization method. The ring was an alloy ring of platinum and iridium. In addition, the interfacial tension between water and some oils was performed in the same manner, and the measurement results are shown in FIGS. 1 and 2. As shown in FIG. 1, the polyethoxylated retinamide derivative of Chemical Formula 1 was adsorbed on the surface in an aqueous solution to reduce the surface tension of water, and was saturated at 5 × 10 ⁻⁵ mol. The surface tension was 40 dyne / cm at that time. . 2 shows that the polyethoxylated retinamide derivative of Formula 1 is adsorbed at the interface between oil and water, thereby reducing the interfacial tension. These results show that the raw material is oriented at both water, oil, or the interface of water and oil.

Experiment 2: Preservation Stability Test of Polyethoxylated Retinamide Derivatives of Formula 1 according to Solvents (R: Methyl, n: 10.7)

A 0.2% aqueous solution of a polyethoxylated retinamide derivative of formula (1) wherein R is methyl and n is 10.7 is mixed 1: 1 with caprylic capric triglyceride (40 milliliters) and placed in a stoppered glass test tube, followed by shaking incubator ( shaking incubator) and shaking at 150 rpm at 40 ° C. for 72 hours. After shaking, the oil layer, the emulsion layer, and the water layer can be seen as shown in FIG. This was again stored in a 40 ° C. thermostat for one month, and the oil layer, the emulsion layer and the water layer were fractionated with a syringe to test the storage stability over time by calibrating the polyethoxylated retinamide derivative of Chemical Formula 1 by HPLC. Dilutions for calibration were first diluted 5 times with purified water and then diluted 15 times with methanol, shaken for 30 minutes with a vortex mixer, and extracted with a sonicator for 1 hour. As can be seen in Table 2, the raw material of Formula 1 was the least stable when present in water.

Preservation Stability of the Formula 1 Raw Material (R: Methyl, n: 10.7) in Water, Oil, and Emulsified Layers division 1 parking 2 parking 3 parking 4 parking Water layer 78 67 54 42 Oil layer 92 87 84 79 Oil painting layer 93 87 85 83

Survival rate (%)

Experiment 2: Evaluate the Effect of Inhibiting Photoaging

In this example, the effect of inhibiting skin photoaging by ultraviolet rays was tested as follows (Bisset PL, et al Photodermatol. Photoimmunol. Phtomed 7: 56-62,1990). 60 hairless mice of about 10 weeks of age were divided into 6 groups of 10 animals, and then UV light B was used three times a week for 30 weeks at a light intensity of 30 mJ / cm 2 using an ultraviolet lamp (Westinghouse FS-40 Sunlamp × 4). Investigate. Example 1, 3, 5 was apply | coated to three experimental groups 2 hours before irradiation, and each base is apply | coated to the other three groups. The extent of wrinkles was determined 1 week after the last UV irradiation. The criterion was determined by four stages of no improvement, slight improvement, severity improvement, and significant improvement compared to each base application group, and the results are shown in Table 3.

Wrinkle generation suppression effect by the ultraviolet rays of the embodiments of the present invention (mari) No improvement Minor improvements Moderate improvement A significant improvement Example 1 One 2 6 2 Example 3 2 3 3 2 Example 5 0 2 4 4

As can be seen in Table 3, the embodiments of the present invention effectively prevent wrinkles caused by ultraviolet rays in hairless mice. This means that the present invention can effectively prevent or reduce light aging due to ultraviolet rays when used as an external preparation for application to the skin.

Experiment 3. Wrinkle Improvement

The wrinkle improvement effect was evaluated about the said Example.

Twenty females in their 30s were asked to apply the base and Examples 2 and 6 once daily for three months to the periphery wrinkles. The wrinkle improvement state was visually observed to determine four stages of no improvement, slight improvement, moderate improvement, and significant improvement, and the results are shown in Table 4.

Wrinkle improvement effect of embodiments according to the present invention No improvement Minor improvements Moderate improvement A significant improvement Mechanism 16 4 One Example 2 3 8 7 2 Example 4 2 8 10

As can be seen in Table 4, the embodiments according to the present invention show an effect of improving wrinkles on the wrinkled skin of the eyes. This means that the present invention alleviates and improves wrinkles when used as an external preparation for application to the skin.

Experiment 4: Stability of Polyethoxylated Retinamide Derivatives (R: Methyl, n: 10.7)

Comparative Examples 1 and 6, Example 7, and Example 8 were placed in a glass test tube with a 50 milliliter stopper and stored in a 45 ° C. thermostat for 4 months, and the polyethoxylated retinamide derivative (R: methyl, n = 10.7) was maintained at 1 month intervals. ) Was calibrated by HPLC. The dilution for calibration was first diluted 5 times with the sample of Comparative Example, purified water and then diluted 15 times with methanol, shaken for 30 minutes with a vortex mixer, and then extracted with a sonicator for 1 hour. The results are shown in Table 5. As shown in Table 5, the polyethoxylated retinamide derivatives have an increased storage capacity according to the application of antioxidants, and especially when the magnesium sulfate, a divalent metal salt, is used together, the storage capacity is increased and thus the stability is excellent. It was confirmed to maximize the anti-wrinkle effect of the derivative.

Stability of the Formula 1 Raw Material (R: Methyl, n: 10.7) in Comparative Examples and Examples 1 month tea 2 moon tea 3 moon tea 4 moon tea Comparative Example 1 87 76 68 54 Example 6 94 87 80 71 Example 7 95 91 84 81 Example 8 98 94 89 86

The composition according to the present invention containing polyethoxylated retinamide as described above is excellent in the anti-aging effect.

Claims (4)

A cosmetic composition for preventing skin aging, comprising 0.001 to 50% by weight of a polyethoxylated retinamide derivative of formula (1): Where R is hydrogen or a C _1-6 alkyl group, n is a number from 2 to 100. The cosmetic composition for preventing skin aging according to claim 1, further comprising 0.01 to 5.0% by weight of antioxidant and 0.001 to 5.0% by weight of divalent metal salt. The anti-aging agent according to claim 2, wherein the antioxidant is at least one selected from the group consisting of rhodiola sac extract, nordihydroguairetinic acid, tocopherol, tocopheryl acetate, butylhydroxytoluene and butylhydroxyanisole. Cosmetic composition. The anti-aging agent according to claim 2, wherein the divalent metal salt is at least one member selected from the group consisting of magnesium sulfate, magnesium stearate, magnesium acetylsalicylate, potassium hydroxide, barium sulfate, zinc sulfate, strontium chloride and strontium bromide. Cosmetic composition.