DE2416556A1 - Skin care compsns contg. moisture-retaining agents - comprising N-hydroxyalkylated, non aromatic N-heterocyclic cpds - Google Patents

Abstract

Skin cleaning- and protective agents are based on the usual components such as emulsifiers, fatty substances, vegetable extracts, solvents, perfumes, thickeners and preservatives, together with 1-20 wt. %, esp. 3-10 wt. % on total compsn. of N-hydroxyalkylsubstitued non-aromatic N-heterocyclic cpds. or their salts of formula (I):- (where R1 = 1-6C (di)hydroxyalkyl gp.; R2=1-4C alkylene chain opt. substd. by low alkyl, hydroxyalkyl, OH or carbonyl oxygen gps., R3 = direct bond or as R2 and X = O, imino gp., which is opt. substd. by 1-6C (di)hydroxyalkyl gp., or a methylene gp., such that R2, R3, X and the N atom form a 5- or 6- ring). (I) act as moisture-retaining agents and maintain or replace moisture lost from the skin due to environmental effects.

Description

"Skin care and skin protection agents containing skin moisturizers The invention relates to skin care and skin protection agents containing nitrogen hydroxyalkyl-substituted non-aromatic N-heterocycles as skin moisturizers.

It is common knowledge that to protect the healthy A certain hygroscopicity belongs among other factors. Will the substances on which this hygroscopicity and its ongoing restoration are based, the skin due to environmental influences, such as repeated washing with highly wetting agents and extracted substances, chemical influences, strong weather influences removed, changes occur in the horny layer, through which the protective effect of the Skin against harmful environmental influences can be greatly reduced.

The task was therefore to add skin care and skin protection agents develop, through which the functionality of the skin despite damaging environmental influences remains fully or to a greater extent and in the event of damage the restoration of the cornea is effectively supported.

This object was achieved by using skin care and skin protection agents based on conventional ingredients such as emulsifiers, fatty substances, plant extracts, solvents, fertilizers, thickeners and preservatives with a content of non-aromatic N-heterocycles substituted on the nitrogen atom hydroxyalkyl-substituted or their salts in general formula in which R1 can stand for a hydroxyalkyl or dihydroxyalkyl group with 1 - 6 carbon atoms, R2 for an alkylene chain with 1 - 4 carbon atoms which is optionally substituted by short-chain alkyl, hydroxyalkyl groups, hydroxyl groups or carbonyl oxygen, R3 can represent a direct bond or an optionally short-chain alkyl chain , Hydroxyalkyl groups, hydroxyl groups or carbonyl oxygen-substituted alkylene chain with 1 - 4 carbon atoms and X denotes oxygen, an imino group optionally substituted by a hydroxyalkyl or dihydroxyalkyl group with 1 - 6 carbon atoms or a methylene group, with the proviso that the nitrogen atom together with R2, X and R3 form a five- or six-membered ring system, in an amount of 1 to 20 percent by weight, preferably 3 to 10 percent by weight, based on the total agent.

These products to be used according to the invention are excellent Way suitable to maintain or restore the water retention of the skin and thereby keeping the skin soft, flexible and fully functional.

The production of the invention as skin moisturizers too The compounds used can be carried out by generally known processes. So lets 2-Hydroxy-2-methyl-4- (2-hydroxyethyl) morpholine according to the information from B.M. Mikhailov and on. Makarova in Zhur. Obshchei Khim 27, 2526-32 from NH (CH2-CH2OH) 2 and BrCH2-COCH3 manufacture at 500C.

N- (2'-hydroxyethyl) -2-ethyl-oxazolidine is obtained according to the British Patent 839 289 by converting diethanolamine and acetaldehyde in benzene at boiling temperature. N, N'-bis (2'hydroxyethyl) -2-imidazolidone can be according to the American Patent 2,847,418 from monoethanolamine, diethanolamine and carbon monoxide obtained at 130 0C under high pressure. The production of N-tris (hydroxymethyl) methylmorpholine is used by J.S. Pierce and J. Wotiz in the Journal of the American Chemical Society 66, 880 (1944).

N- (2'-hydroxyethyl) -2-hydroxymethyl-morpholine is obtained after Information from A.A. Schleppnik and C.D. Gutsche in the Journal of Organic Chemistry 25, 1381 (1960) by reacting diethanolamine, epichlorohydrin and sodium ethylate. Many of the compounds to be used according to the invention can be converted by reaction of the corresponding N-heterocycles obtained with alkylene oxides, as described in the monograph "Epoxides and their Derivatives" by M.S. Malinovskii, Israel Program for Scientific Translations, Jerusalem 1965, on pages 249 ff.

According to the invention, hydroxyalkyl-substituted on the nitrogen atom, non-aromatic N-heterocycles are, for example, N- (2'-hydroxyethyl) piperidine, N- (21 3'-dihydroxypropyl) -piperidine, N- (2'-hydroxy-2'-methylpropyl) -piperidine, N- (1'-methyl-2'-hydroxy-2'-methylpropyl) piperidine, N- (2'-hydroxyethyl) -2-piperidone, N- (2'-hydroxyethyl) piperazine, N, N'-bis (2'-hydroxyethyl) piperazine, N, N'-bis (2'-hydroxypropyl) piperazine, N, N'-bis (2'-hydroxy-2'-methylpropyl) -piperazine, -N- (2'-hydroxy-2'-methylbutyl) -piperazine, N, N'-bis- (2'-hydroxy-2'-methylbutyl) -piperazine, N, N'-bis- (1'-methyl-2'-hydroxy-2'-methylpropyS) -piperazine, N- (2'-hydroxyethyl) -3-oxo-piperazine, N, N'-bis (2'-hydroxypropyl) -2,5-dimethyl-piperazine, N- (2'-Hydroxyethyl) -piperidazine, N- (2'-HydroxySthyl) -pyrrolidine, N- (2'-Hydroxypropyl) -pyrrolidine N- (2'-hydroxyethyl) -2,5-dimethyl-pyrrolidine, N- (2'-hydroxypropyl) -2-pyrrolidone, N, N'-bis (2'-hydroxyethyl) -2-imidazolidone, N- (2'-hydroxyethyl) oxazolidine, N- (2w-hydroxyethyl) -2-methyloxazolidine, N- (2'-hydroxyethyl) -2-ethyl-oxazolidine, N- (2'-hydroxyethyl) -morpholine, N- (2'-hydroxypropyl) -morpholine, N- (21 3'-dihydroxypropyl) -morpholine, N- (2'-hydroxyethyl) -2-hydroxymethyl-morpholine, N- (2'-hydroxyethyl) -2-hydroxy-2-methyl-morpholine, N-tris (hydroxymethyl) methylmorpholine, ß-hydroxyethyl succinimide. You can find in the skin care and skin protection products are mainly used in the form of their salts.

As salts of the non-aromatic compounds listed above and hydroxyalkyl-substituted on the nitrogen atom Heterocycles come, for example, the halides, especially chlorides, sulfates, Phosphates, acetates, lactates, tartrates, citrates, glycolates, oxalates, fumarates, succinates and malate in question.

The salts are preferably adjusted so that they are concentrated in aqueous solution have a pH of 6.

All of the aforementioned salts are completely colorless and odorless stable products that have excellent physiological compatibility and no adverse effects on the skin care and skin care products associated with them Have skin protectants.

As a skin care and skin protection agent, which by the addition of the invention to be used, non-aromatic heterocycles which are hydroxyalkyl-substituted on the nitrogen respectively.

the salts of which are given special skin-care properties, are day creams, baby creams, night and nourishing creams, cleansing creams, protective skin creams, Glycerine creams, creams with special additives of animal and vegetable origin, To mention sun protection creams and sun protection emulsions, face tonic, aftershave. Incorporation into the skin care and skin protection agents can be carried out in a known manner by simply stirring in or dissolving. In addition to the to be used according to the invention, nonaromatic heterocycles or heterocycles thereof which are hydroxyalkyl-substituted on the nitrogen The cosmetic preparations can salt those normally present in them Components, such as B. emulsifiers, fatty substances, plant extracts, preservatives, fragrances, Solvent contained in conventional amounts.

The pH of skin care and skin protection products can be in the range Move from acidic to neutral and is conveniently set to weakly acidic values adjusted to pH 6.

The following examples are intended to illustrate the subject matter of the invention in greater detail explain without, however, restricting it to this.

.Examples of those to be used according to the invention as skin moisturizers, nonaromatic N-heterocycles which are hydroxyalkyl-substituted on the nitrogen atom The compounds listed below are subjected to the tests and in formulations used.

A) N- (2'-hydroxyethyl) piperazine. HCl (pH 6) The product was after prepared from ethylene oxide and piperazine according to the information provided by M. S. Malinovskii and adjusted to pH 6 with HCl.

B) N- (2 ', 3t-dihydroxypropyl) piperidine. HC1 (pH 6) The compound according to the information provided by M. S.

Malinovskii by reacting piperidine with 1-chloro-propanediol-2,3 obtain.

C) N- (2'-hydroxyethyl) morpholine.

The connection was established according to the information provided by M. S. Malinovskii from ethylene oxide and morpholine.

The favorable behavior of the compounds to be used according to the invention with regard to water absorption capacity and water retention capacity was determined by means of test methods described in more detail below.

The water absorption capacity was determined by measurement the weight increase when stored at 100% relative humidity over 48 hours in mg of water per 100 mg of substance.

The water retention capacity was determined by determining the Residual water content of a sample moistened with 300 mg of water per 100 mg of substance after storage at 0% relative humidity under a pressure of 12 torr during a time of 45 minutes, 1 1/2 hours and 8 hours as mg of water per 100 mg Substance.

The measured values listed in Table 1 below were obtained obtain.

Table 1 Water retention and water absorption capacity of non-aromatic N-heterocycles which are hydroxyalkyl-substituted on the nitrogen atom. Product water retention in mg / 100 mg substance water absorption in mg / 100 mg substance: after 45 min. after 90 min. after 8 hours after 118 hours A 114 81 12 375 B 102 52 8 228 C 126 45 6 104 In addition to the strong water absorption capacity, the table above also shows the considerable water retention capacity of the compounds to be used according to the invention and thus their good suitability as skin moisturizers in skin care and skin protection agents.

A few more examples of cosmetic preparations are given below listed the substances to be used according to the invention as skin moisturizers contain.

Day cream low-fat fatty acid partial glyceride Cutina MD (R) Dehydag 6.0 parts by weight of stearic acid 8.0 mixture of non-ionic emulsifiers Eumulgin C 700 (R) Dehydag 3.0 2 Octyldodecanol 4.0 "Vegetable Oil 3.0 Paraffin Oil 5.0 Triethanolamine 0.4 "1,2-propylene glycol 3.0 product A 3.0 Nipagin M 0.2 perfume oil 1.0 water 63.11 Baby cream mixture of higher molecular esters, mainly mixed esters of pentaerythritol fatty acid esters and citric acid fatty alcohol ester Dehymuls E (R) Dehydag 7.0 parts by weight of oleic acid decyl ester 10.0 Vaseline 10.0 Wool fat 5.0 Boric acid 0.2 Talc 12.0 Zinc oxide 8.0 Nipagin M. 0.2 product B 5.0 water 42.6 Night cream colloidal mixture from 90 parts of cetostearyl alcohol and 10 parts of sodium lauryl sulfate 10.0 parts by weight 2-octyldodecanol 12.0 vegetable oil 7.0 wool fat 2.0 glycerine 1.0 product C 5.0 n nipagin M 0.2 Perfume oil 1.0 Water 61.8 Boron-glycerine cream Colloid-disperse mixture of 90 Parts of cetostearyl alcohol and 10 parts of sodium lauryl sulfate, 12.0 parts by weight of 2-octyldodecanol 8.0 Vegetable Oil 5.0 Boric Acid 2.0 Glycerin 28.0 Nipagin M 0.2 Product A 3.0 "Water 41.8 "sun protection cream Mixture of higher molecular esters with fatty substances Dehymuls K (R) Dehydag 30.0 parts by weight decyl ester 15.0 light stabilizer 5.0 nipagin M 0.2 product B 3.0 water 46.8 Face mask mixture of fatty acid partial glyceride with emulsifiers Cutina LE (R) Dehydag 12.0 parts by weight of decyl olate 4.0 vitamin oil 5.0 kaolin 2.0 rice starch 5.0 n nipagin M 0.2 product C 6.0 water 67.8 aftershave Oleyl cetyl alcohol 1.0 part by weight ethanol 96% 67.5 menthol 0.2 camphor 0.2 balsam of Peru 0.1 Perfume 0.5 Hammamelis Extract 10.0 Boric Acid 0.5 Product B 10.0 Water 10.0 Facial Toner Cucumber juice 15.0 parts by weight citric acid 0.2 ethanol 96% 15.0 product A 10.0 fragrance 1.0 water 58.8 instead of those mentioned in the above formulations according to the invention The compounds to be used can also be other of those listed with equal success products to be used according to the invention occur.

Claims (4)

Claims Xf) Skin care and skin protection agents based on common ingredients such as emulsifiers, fatty substances, plant extracts, solvents, fragrances, thickening preservatives, characterized by a content of hydroxyalkyl-substituted, non-aromatic N-heterocycles or their salts of the general formula in which R1 can stand for a hydroxyalkyl or dihydroxyalkyl group with 1 - 6 carbon atoms, R2 for an alkylene chain with 1 - Li carbon atoms which is optionally substituted by short-chain alkyl, hydroxyalkyl groups, hydroxyl groups or corbonyl oxygen, R3 can be a direct bond or an optionally short-chain alkyl , Hydroxyalkyl groups, hydroxyl groups or carbonyl oxygen-substituted alkylene chain with 1 - 4 carbon atoms and X denotes oxygen, an imino group optionally substituted by a hydroxyalkyl or dihydroxyalkyl group with 1 - 6 carbon atoms or a methylene group, with the proviso that the nitrogen atom together with R2, X and R3 form a five- or six-membered ring system, in an amount of 1 to 20 percent by weight, preferably 3 to 10 percent by weight, based on the total agent. 2. Skin care and skin protection agents according to claim 1, characterized in that that they are the non-aromatic N-heterocycles which are hydroxyalkyl-substituted on the nitrogen atom in the form of their halides, in particular chlorides, sulfates, phosphates, acetates, lactates, Contains tartrates, citrates, glycolates, oxalates, fumarates, succinates and malates. 3. skin care and skin protection agent according to claim 1 and 2, characterized characterized in that they act as a skin moisturizer on the nitrogen atom hydroxyalkyl-substituted, non-aromatic N-heterocycles or their salts common ingredients such as emulsifiers, fatty substances, plant extracts, preservatives, Contains fragrances, thickeners, solvents in the conventional quantities. 4. Skin care and skin protection agents according to claim 1 - 3, characterized in that that their pH is adjusted to weakly acidic values around pH 6.