CH626534A5 - Cosmetic composition with a content of humectant for the skin - Google Patents

Description

626 534

2nd

PATENT CLAIM Cosmetic agent, characterized in that it contains at least one N-hydroxyalkyl alkanoic acid amide of the formula as a skin moisturizer

/ R2

R ± - CON ^

wherein Ri is hydrogen or alkyl with 1-4 C atoms, R2 hydroxyalkyl with 2-6 C atoms and 1-5 hydroxyl groups and R3 hydrogen, alkyl with 1-4 C atoms or hydroxyalkyl with 2-6 C atoms and 1-5 hydroxyl groups, in a proportion of 1-20 wt .-%, based on the total weight of the agent.

The invention relates to a cosmetic agent, in particular skin care, skin protection and skin cleaning agent, containing N-hydroxyalkyl alkanoic acid amides as skin moisturizers.

It is well known that protective measures for healthy skin include a certain hygroscopicity, among other factors. If the substances on which this hygroscopicity and its ongoing restoration are based are removed from the skin by environmental influences, such as repeated washing with strongly wetting and extracting substances, chemical influences, strong weather influences, changes occur in the horny layer, through which the protective effect of the skin can be greatly reduced against damaging environmental influences.

It was therefore the task to develop cosmetic agents, in particular skin care, skin protection and skin cleansing agents, through which the functionality of the skin is retained in full or to an increased extent despite damaging environmental influences and effectively supports the restoration of the cornea in the event of damage becomes.

The products hitherto used as skin moisturizers consisted entirely of ionic compounds, such as acids and primarily salts, which in some cases provided useful results as skin moisture regulators, but their incorporation into cosmetic preparations often caused difficulties. especially when it came to sensitive emulsion bases. In such cases, it was often only possible to incorporate completely inadequate amounts of skin moisture regulators. In addition to the general task of developing good skin moisturizers, there was particular interest in products that do not pose any difficulties when incorporated, even in sensitive cosmetic emulsions.

This object was achieved in that cosmetic agents, in particular skin care, skin protection and skin cleansing agents, based on customary ingredients, such as surfactants, emulsifiers, fatty substances, plant extracts, solvents, fragrances, thickeners, preservatives, were used, containing N- Hydroxyalkyl alkanoic acid amides of the formula

R1 - CON ^

in which Rx is hydrogen or an alkyl radical with 1-4 carbon atoms, R2 for a hydroxyalkyl radical with 2-6 carbon atoms and 1-5 hydroxyl groups and R3 for hydrogen, an alkyl radical with IA carbon atoms or a hydroxyalkyl radical with 2-6 carbon atoms and 1 5 hydroxyl groups are in an amount of 1-20% by weight, preferably 3-10% by weight, based on the total agent.

These products to be used in the agent according to the invention are excellently suited to maintaining or restoring the water retention of the skin and thereby keeping the skin soft and flexible and fully functional.

The compounds described, which are to be used as skin moisturizers, can be prepared by generally known processes. For example, they can be obtained by aminolysis of the alkyl esters of the corresponding alkanoic acids in a solvent-free manner or in solvents such as alkanols, dioxane or tetrahydrofuran. Furthermore, the N-hydroxyalkylalkanoic acid amides can be obtained from the alkanoic acids and the corresponding amines by heating to a higher temperature with or without solvent. The solvents for azeotropic water separation can be e.g. Toluene, xylene, chlorobenzene or ligroin are used.

Suitable N-hydroxyalkyl alkanoic acid amides are e.g. N- (2-hydroxyethyl) acetamide, hydroxyethyl) acetamide,

N- (2-hydroxyethyl) formamide, N- (2-hydroxyethyl) propionamide, N- (2-hydroxyethyl) butyl amide, N- (2-hydroxyethyl) pivalic acid amide, N- (2-hydroxyethyl) valeramide, 2- (2-hydroxypropyl) formamide, N- (2-hydroxypropyl) acetamide, N- (2-hydroxypropyl) propionamide, N- (2-hydroxypropyl) butyramide, N- (2-hydroxypropyl) pivalic acid amide, N- (2-hydroxypropyl) -valeramide, N- (3-hydroxypropyl) -formamide, N- (3-hydroxypropyl) -acetamide, N- (3-hydroxypropyl) -propionamide, N- (3-hydroxypropyl) -butyramide, N- (3-hydroxypropyl) pivalic acid amide, N- (3-hydroxypropyl) valeramide, N- (2-hydroxybutyl) formamide,

N- (2-hydroxybutyl) acetamide, N- (2-hydroxybutyl) propionamide, N- (2-hydroxybutyl) butyramide, N- (2-hydroxybutyl) pivalic acid amide, N- (2-hydroxybutyl) valeramide, N- (1-Hydroxy-2-methyl-2-propyl) formamide, N- (l-hydroxy-2-methyl-2-propyl) -acetamide, N- (l-hydroxy-2-methyl-2-propyl ) -propionamide, N- (l-hydroxy-2-methyl-2-propyl) -butyramide, N- (l-hydroxy-2-methyl-2-propyl) -pivalic acid amide, N- (1-hydroxy-2-methyl -2-propyl) valeramide, N- (2,3-dihydroxypropyl) formamide, N- (2,3-dihydroxypropyl) acetamide, N- (2,3-dihydroxypropyl) propionamide, N- (2,3 -Dihydroxypropyl) -butyramide, N- (2,3-dihydroxypropyl) -pivalic acid amide, N- (2,3-dihydroxypropyl) -valeramide, N- (1,3-dihydroxy-2-propyl) -formamide, N- (l , 3-dihydroxy-2-propyl) -acetamide, N- (1,3-dihydroxy-2-propyl) -propionamide, N- (1,3-dihydroxy-2-propyl) -butyramide, N- (1,3 Dihydroxy-2-propyl) -pivalic acid amide, N- (1,3-dihydroxy-2-propyl) -valeramide, N- (1,3-dihydroxy-2-methyl-2-propyl) -formamide,

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626 534

N- (1,3-dihydroxy-2-methyl-2-propyl) acetamide,

N- (1,3-dihydroxy-2-methyl-2-propyl) propionamide,

N- (1,3-dihydroxy-2-methyl-2-propyl) -butyramide,

N- (1,3-dihydroxy-2-methyl-2-propyl) -pivalic acid amide,

N- (1,3-dihydroxy-2-methyl-2-propyl) valeramide,

N- (1,3-dihydroxy-2-ethyl-2-propyl) formamide,

N- (1,3-dihydroxy-2-ethyl-2-propyl) acetamide,

N- (1,3-dihydroxy-2-ethyl-2-propyl) propionamide,

N- (1,3-dihydroxy-2-ethyl-2-propyl) -butyramide,

N- (1,3-dihydroxy-2-ethyl-2-propyl) -pivalic acid amide,

N- (1,3-dihydroxy-2-ethyl-2-propyl) -valeramide, •

N- (trishydroxymethyl-methyl) formamide,

N- (trishydroxymethyl-methyl) -acetamide,

N- (trishydroxymethyl-methyl) propionamide,

N- (trishydroxymethyl-methyl) -butyramide,

N- (trishydroxymethyl-methyl) -pivalic acid amide,

N- (trishydroxymethyl-methyl) -valeramide,

N- (2-hydroxyethyl) -N-methyl-formamide,

N- (2-hydroxyethyl) -N-methyl-acetamide,

N- (2-hydroxyethyl) -N-methyl-propionamide,

N- (2-hydroxyethyl) -N-methylbutyramide,

N- (2-hydroxyethyl) -N-methyl-pivalic acid amide,

N- (2-hydroxyethyl) -N-methylvaleramide,

N- (2-hydroxypropyl) -N-methyl-formamide,

N- (2-hydroxypropyl) -N-methyl-acetamide,

N- (2-hydroxypropyl) -N-methyl-propionamide,

N- (2-hydroxypropyl) -N-methylbutyramide,

N- (2-hydroxypropyl) -N-methyl-pivalic acid amide,

N- (2-hydroxypropyl) -N-methylvaleramide,

N- (2,3-dihydroxypropyl) -N-ethyl-formamide,

N- (2,3-dihydroxypropyl) -N-ethyI-acetamide,

N- (2,3-dihydroxypropyl) -N-ethyl-propionamide,

N- (2,3-dihydroxypropyl) -N-ethyI-butyramide,

N- (2,3-dihydroxypropyl) -N-ethyl-pivalic acid amide,

N- (2,3-dihydroxypropyl) -N-ethyl-valeramide,

N- (2,3,4,5,6-pentahydroxyhexyl) formamide,

N- (2,3,4,5,6-pentahydroxyhexyl) acetamide,

N- (2,3,4,5,6-pentahydroxyhexyl) propionamide,

N- (2,3,4,5,6-pentahydroxyhexyl) -butyramide,

N- (2,3,4,5,6-pentahydroxyhexyl) pivalic acid amide,

N- (2,3,4,5,6-pentahydroxyhexyl) valeramide,

N- (l, 3,4,5,6-penta-hydroxy-2-hexyl) formamide,

N- (1,3,4,5,6-penta-hydroxy-2-hexyl) acetamide,

N- (1,3,4,5,6-penta-hydroxy-2-hexyl) propionamide,

N- (l, 3,4,5,6-penta-hydroxy-2-hexyl) -butyramide,

N- (l, 3,4,5,6-penta-hydroxy-2-hexyl) -pivalic acid amide,

N- (l, 3,4,5,6-penta-hydroxy-2-hexyl) valeramide,

N, N-bis (2-hydroxyethyl) formamide,

N, N-bis (2-hydroxyethyl) acetamide,

N, N-bis (2-hydroxyethyI) propionamide,

N, N-bis- (2-hydroxyethyl) -butyramide,

N, N-bis (2-hydroxyethyl) pivalic acid amide,

N, N-bis (2-hydroxyethyl) valeramide,

N, N-bis (2-hydroxypropyl) formamide,

N, N-bis (2-hydroxypropyl) acetamide,

N, N-bis (2-hydroxypropyl) propionamide,

N, N-bis- (2-hydroxypropyl) -butyramide,

N, N-bis (2-hydroxypropyl) pivalic acid amide,

N, N-bis (2-hydroxypropyl) valeramide.

The N-hydroxyalkyl-alkanoic acid amides described are colorless to pale yellow, crystalline or highly viscous, completely stable products which have very good physiological compatibility and are notable for being neutral, nonionic compounds by particularly easy incorporation into cosmetic emulsion bases.

As skin care, skin protection and skin cleansing agents, which are given special skin care properties by the addition of the N-hydroxyalkylalkanoic acid amides described, day creams, baby creams, night and nutritional creams, cleaning creams, skin protection creams, glycerol creams, creams with special additives are animal and of vegetable origin, sunscreen creams and sunscreen emulsions, soaps, bath oils, bubble baths, shower baths, facial tonic, aftershave. The incorporation into the skin care, skin protection and skin cleaning agent can be carried out in a known manner by simply stirring or dissolving. In addition to the N-hydroxyalkyl alkanoic acid amides described, the cosmetic preparations can contain the constituents which are usually present in these, e.g. Emulsifiers, fatty substances, plant extracts, preservatives, fragrances, solvents contained in conventional amounts. The pH value of the skin care and skin protection agents can range from acid to neutral and is expediently set to weakly acidic values around pH 6. In the case of soap-based skin cleansers, the aim is to make the alkaline setting as weak as possible.

Of the N-hydroxyalkylalkanoic acid amides to be used as skin moisturizers in the agent according to the invention, the compounds listed below were subjected to the tests and used in recipes.

A. N- (2-hydroxyethyl) acetamide (Beilstein 4.1430)

Manufacturing

A mixture of 91.6 g (1.5 mol) of ethanolamine and 200 ml (approx. 2 mol) of ethyl acetate was heated to boiling for 18 hours and the reaction product was distilled twice under reduced pressure. 102 g (66% of theory) of N- (2-hydroxyethyl) acetamide with a boiling point of 125-127 ° C./0.01 Torr and n20 1.4720 were obtained.

The following carboxamides were prepared in an analogous manner.

B. N- (2-hydroxypropyl) acetamide (J.O.C. (B) 1966, 690)

Bp 108 ° C / 0.01 torr; n20 1.4670.

C. N- (1,3-Dihydroxy-2-methyl-2-propyl) acetamide

Mp 111-112 ° C (from ethanol).

D. N, N-bis (2-hydroxyethyl) acetamide colorless oil.

E. N- (2-hydroxypropyl) formamide

Bp 114-115 ° C / 0.01 Torr; n20 1.4723.

F. N- (1,3-Dihydroxy-2-methyl-2-propyl) formamide light yellow oil. n20 1.4972.

G. N, N-bis (2-hydroxyethyl) formamide bp 120 ° C / 0.01 Torr; n20 1.4848.

H. N, N-bis (2-hydroxypropyl) formamide colorless oil, n20 1.4795.

I. N- (2-hydroxyethyl) propionamide (JACS 59, 111 (1937)

Bp 115-117 ° C / 0.01 Torr, n20 1.4685.

J. N- (2-hydroxypropyl) propionamide bp 117 ° C / 0.01 torr; n20 1.4647.

K. N- (1,3-Dihydroxy-2-methyl-2-propyl) -propionamide mp 97-98 ° C (from ethanol).

The favorable behavior of the described compounds with regard to water absorption and water retention was determined using the test methods described in more detail below. It is a Ver5

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626 534

4th

drive to determine the equilibrium moisture, which is a measure of the water retention, and to determine the water retention, rehydration and elasticity of impregnated pig epidermis.

1. Determination of the equilibrium moisture

The substances to be examined (approx. 300-500 mg) were moistened with a defined amount of water and exposed to various relative atmospheric humidities (1, 30, 47, 65, 89 and 100% relative humidity) at 23 ° C for 24 hours. The amount of water taken up or released was determined gravimetrically and plotted graphically. From the curves resulting from this, it can be concluded that relative humidity at which there is neither water release nor water absorption. This value, known as equilibrium moisture, is a measure of the water retention capacity of a substance. The lower the value, the more positive the product should be assessed. The water absorption capacity (hygroscopicity) of the substance can also be read from the steepness of the curve.

2. Measurements on the pig epidermis a) Extraction of the pig epidermis

Immediately after the pigs have been killed, the bristles of the skin are cut off using a hair clipper (shaving head 0.1 mm). The pigs are scalded in water at 60 ° C for approx. 1-5 minutes, the epidermis is then peeled off and stored at -20 ° C until use.

b) Determination of water retention and rehydration of impregnated pig epidermis

Punched-out pieces of epidermis (1x2 cm) were bathed in 10% strength by weight solution of the test substance for two hours, dabbed under standardized conditions using a small press and suspended for 24 hours between 2 clamps in a 100 ml Erlenmeier flask at 23 ° C and 30% relative humidity and 50 % relative humidity (adjusted by sulfuric acid-water mixtures) dried. The drying out of the impregnated sample to X% of the initial weight was compared with the corresponding value of the epidermis bathed only in water (blank value). The table shows the improvement in water retention and rehydration compared to the blank value in% H20. The deviations in the respective double tests were a maximum of ± 2 absolute units. The experiment was repeated for larger deviations. The rehydration was determined analogously by drying 15 of the impregnated and dabbed pork epidermis for 24 hours at 30% relative humidity and then for 24 hours at 90% relative humidity.

c) Elasticity measurements on impregnated porcine epidermis Punched-out epidermal pieces (1x6 cm) were bathed in 10% by weight aqueous solution of the substance to be tested and blotted under standardized conditions. The samples were incubated between 2 clamps free-hanging at 75% relative humidity and 90% relative humidity for 24 hours and stretched in a Zwick tensile testing machine (type: 1402) at 0-50 p load. The elongation in mm was given as a measure of the elasticity and was measured in Hooke's range at a load between 5-30 p.

The measured values obtained in the tests described above are shown in Table 1 below.

20th

Table 1

Product measurements on the pig epidermis

Equal water retention rehydration weight% H20 after drying out with% water moisture increase

(% RH) 30% RH 50% RH 90% RH

mm elongation after loading between 5-30 g

90% RH

75% RH

Blank value

-

0

0

0

0.3-0.5

0

A

54

15

15

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3.4

0.3

B

60

10th

15

32

2.5

-

C.

75

10th

13

31

4.0

0.5

E

59

16

19th

19th

4.8

0.5

F

68

9

12th

20th

2.2

0.6

H

68

9

12th

23

2.5

0.7

I.

68

9

9

36

5.1

0.3

J

71

8th

10th

21st

3.4

0.5

K

88

3rd

9

15

3.0

0.6

In addition to the strong water absorption capacity, the table above also shows the remarkable water retention capacity of the compounds described and thus their suitability as skin moisturizers in skin care, skin protection and skin cleaning agents.

Below are some examples of cosmetic preparations that contain the substances described as skin moisturizers.

1. Day cream slightly greasy

Partial fatty acid glyceride "Cutina" MD parts by weight

Dehydag 6.0

Stearic acid 8.0 Mixture of nonionic emulsifiers

"Emulgin" C 700® Dehydag 3.0

2-octyldodecanol 4.0

Vegetable oil 3.0

Paraffin oil 5.0

55 triethanolamine 0.4

1,2-propylene glycol 3.0

Product A 6.0

"Nipagin" M 0.2

Perfume oil 1.0

60 water 60.4 2nd baby cream mixture of high molecular weight esters, parts by weight predominantly mixed esters of pentaerythritol fatty acid ester and citric acid fatty acid

65 alcohol esters «Dehymuls» E® Dehydag 7.0

Oleic acid decyl ester 10.0

Vaseline 10.0

Wool fat 5.0

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626 534

Boric acid

0.2

Ethanol 96% 15.0

talc

12.0

Product A 5.0

zinc oxide

8.0

Product B 5.0

"Nipagin" M

0.2

Perfume 1.0

Product B

8.0

5

Water 58.8

water

39.6

9. Bubble bath

3. Night cream

Monoethanolamine lauryl sulfate parts by weight

Colloid-disperse mixture of

Parts by weight

approx. 33% active washing substance (WAS) 66.0

90 parts of cetylstearyl alcohol and

Coconut fatty acid diethanolamide 3.0

10 parts of sodium lauryl sulfate

10.0

10th

Product K 10.0

2-octyldodecanol

12.0

Perfume oil 3.0

Vegetable oil

7.0

Water 18.0

Wool fat

2.0

10. Cream bubble bath

Glycerin

1.0

Sodium lauryl ether sulfate parts by weight

Product C

10.0

15

approx. 30% WAS 78.0

"Nipagin" M

0.2

Oleic acid diethanolamide 4.0

Perfume oil

1.0

Hexyl laurate 8.0

water

56.8

Product E 5.0

4. Boron glycerin cream

1,2-propylene glycol 2.0

Colloid-disperse mixture of

Parts by weight

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Perfume oil 3.0

90 parts of cetylstearyl alcohol and

11. Soap containing skin moisturizers

10 parts of sodium lauryl sulfate

12.0

It was 80% by weight of sodium tallow soap

2-octyldodecano1

8.0

and a mixture of 20% sodium coconut soap

Vegetable oil

5.0

used. The soap in the form of flakes with egg

Boric acid

2.0

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A water content of 20% was included

Glycerin

28.0

0.2 parts by weight of l-hydroxyethane-l, l-diphosphonic acid,

"Nipagin" M

0.2

10.0 parts by weight of product A,

Products

6.0

3.0 parts by weight of perfume oil,

water

38.8

based on 100 parts by weight of soap, mixed, in one

5. Sunscreen cream

30th

Extruded press deformed and pressed into pieces.

Mixture of higher molecular esters with

Parts by weight

Fat substances «Dehymuls» K® Dehydag

30.0

Oleic acid decyl ester

15.0

12. Syndet soap bar with a salary

Sunscreen

5.0

of skin moisturizers

"Nipagin" M

0.2

35

In the example, a syndet piece based on a Gemi

Product F

8.0

of olefin sulfonate and sulfoberstein ester salt

water

41.8

placed. The disodium

6. Face mask

salt of a sulfosuccinic acid monofatty alcohol ester, which consists of

Mixture of fatty acid partial glyceride

Parts by weight

the C12-C18 fraction of a coconut fatty alcohol was made using emulsifiers "Cutina" LE Dehydag

12.0

40

that was. The olefin sulfonate was from a mixture

Oleic acid decyl ester

4.0

wheel-chain a-olefins with 15-18 carbon atoms. This

Vitamin oil

5.0

The olefin mixture was obtained by sulfonating 1 mol of olefin with approx.

kaolin

2.0

1.2 moles of gaseous sulfur trioxide diluted with inert gas,

Rice starch

3.0

Hydrolyzing the crude sulfonation product with the

"Nipagin" M

0.2

45 "calculated amount of caustic soda at temperatures of about

Product H

10.0

100 ° C and bleaching of the sulfonate with the help of hypochlorite

water

63.8

been made. The mixture of the two sulfonates contained

7. Aftershave

Parts by weight

about 5% by weight of neutral salts (sodium sulfate and sodium chloride) based on anhydrous sulfonate. The Syndet

Oleyl cetyl alcohol

1.0

50

mass had the following composition:

Ethanol 96%

67.5

70 parts by weight of surfactant mixture consisting of

Methanol

0.2

60% by weight olefin sulfonate

Fighter

0.2

40% by weight disodium salt of the sulfosuccinic acid ester

Peru balsam

0.1

15 parts by weight of tallow fatty acid (JZ 2)

Perfume

0.5

55

2 parts by weight of lanolin

Hammam extract

10.0

5 parts by weight of water

Boric acid

0.5

8 parts by weight of product F

Product I

5.0

2 parts by weight of perfume oil.

Product J

5.0

The mass was deformed in an extrusion press and closed

water

10.0

60

Pieces pressed.

8. Facial toner

Parts by weight

In place of the compounds mentioned in the above formulations, it is also possible with equally good success

Cucumber juice

15.0

of the listed products occur.

Citric acid

0.2

s