MXPA94005923A - Improvements in process to smoke and soften p - Google Patents

Abstract

Certain novel N-alkoxyalkylamides of hydroxy acids are provided for use in providing moisturizing and / or smoothing properties to human skin.

Description

"IMPROVEMENTS IN PROCESS TO SMOKE AND SOFTEN THE SKIN" INVENTOR: JOSEPH P. CIAUDELLI, citizen of EE. UU , with address at 54 Jean Street, Ramsey, New Jersey, USA. UU CAUSAHABIENTE: REVLON, INC., A society of EE. UU., With address at 767 Fifth Avenue, New York, New York, EE. UU EXTRACT OF THE DESCRIPTION Certain N-alkoxyalkylamides of hydroxy acids are provided; novelties; for use in providing moisturizing and / or softening properties to human skin: DESCRIPTIVE MEMORY The present invention relates to certain N-alkoxyalkylamides of hydroxy acids and to the use of such compounds in compositions and methods for providing skin moisturizing and / or softening properties. human, particularly to the "dry skin" common or moderate to moderate. The alteration of human skin known as "dry skin" is characterized by cracking, scaling or exfoliation of the skin of the hands, feet, neck, face or other parts of the body. This alteration can be the result of a hereditary alteration known as ichthyosis, which is a severe form of dry skin. This form of dry skin is not too prevalent. The most common form of "dry skin," which affects a relatively large portion of the population, is a mild to moderate form of dry skin that arises due to exposure to low humidity environmental conditions in autumn and winter climate zones. tempered. These environmental conditions give rise, in the skin areas 3 exposed thereto, to a loss of moisture from said areas of the skin, with the consequent formation of cracks, cracks, crevices or scales, in said affected areas of the skin. Various chemical compounds have been proposed for use in combating said dry skin problems. These compounds are usually formulated with other materials, in order to be useful for topical application to the skin in the form of a lotion, cream or ointment. Examples of such prior art compounds, and topical compositions in which they can be used to treat dry skin, are described, for example, in U.S. Patent 3,230,228; 3,322,635; 4,105,783; 4,197,316; 4,382,765 and in the OLS of West Germany 2, 632,391. The compounds of these references include some hydroxy-containing carboxylic acid amides. The present invention relates to novel compounds of N-alkoxyalkylamide having the general formula: H 2 H 2 CH 2 - (CH 0 H) p-CN- (Cn-H 2n) _ 0 (CmH 2m + 1) (I) wherein p is a whole number from 1 to 4.

(CnH n) is a straight or branched chain alkyl bridge, wherein n is an integer from 1 to 6 and preferably, is 3; and '"in ^ m + l is up to 9'ruP ° alkyl or straight or branched chain, where m is an integer from 1 to 6 and preferably, it is 1. The most preferred amide compound, from the structure I, is that in which p is 4, n is 3 and m is 1. Said compound is metoprilgluconamide, HO-CH2- (CHOH) 4 (CH2) 3-0- (CH3) (II) The amide compounds of structure I of the present invention are prepared under amide-forming conditions by reacting an amine compound having the structure: H2 N- < CnH2n > - ° - (CmH2m + l) d ") where (CnH.2m + l) are as 3e defined above, with a carboxylic acid or a lactone having one of the structures: 0 HO-CH2- (CHOH) -C - (OH (IV)? CH20H (V) in q is a r, »tero c; _t.-O de - k - The preferred amine compounds of said structure IV is gluconic acid. The preferred lactones of said structure V is glucono-delta-lactone, ie, where q is 3. When carrying out the reaction, a mole is contacted. of the amine of structure III with one mole of acid / lactone of structure IV / V, usually an excess of the amine is used to help fill the reaction to completion. Said excess is usually in an amount of 0.1 to 0.5 mole percent. The lactone / acid is first heated with stirring in an alcoholic solvent at reflux, at atmospheric pressure, to form suspension with solids. The alcohol used is aliphatic and has a reflux temperature of around 65 to 85 ° C. The amine is then added dropwise to the suspension, in the refluxing solvent, and the solids are dissolved therein to produce a light yellow solution. The reaction takes about 10 to 30 minutes at reflux temperatures. The reaction is slight exothermic. however, any rise in temperature is only noticeable when the amine is added at room temperature, but it is not detectable at the reflux temperatures of the solvent. The heating is then discontinued and the solution allowed to cool with stirring. Generally, the formation of a precipitate begins approximately 20 degrees below the ambient temperature (about 25 ° C), the solids are filtered off using an Euchner funnel under vacuum. The solids are washed with alcohol solvent. In this way, yields of approximately 90 to 98% are obtained after drying. The compositions of the present invention are intended to be used to treat humans having a dry skin condition. The active ingredient used in said compositions for that purpose is one or more of I03 amide compounds of structure I described above and, preferably, the amide compound of structure II. The compositions of the present invention can be used for prophylactic as well as therapeutic purposes, with respect to their proposed use in treating dry skin by topical application thereto, so as to prevent or cure the occurrence of any cracking, flaking or scaling. ? n, exfoliation or cracking of the skin. Thus, the compositions of the present invention can be used to prevent, cure or ameliorate dry skin conditions and acne, psoriasis, seborrhea, keratosis, diaper rash, sunburn and windburn. The compositions of the present invention may be prepared and used in the form of a lotion, cream, ointment, bar or soap, or other forms commonly employed in the art for skin care formulations. Preferably they are used in an emulsified form.

The compositions of the present invention are prepared by employing effective, skin softening and moisturizing amounts of one or more of the amide compounds of the present invention, is a cosmetically acceptable vehicle, such as a hydrophilic ointment (USP) or petrolatum. When used in said compositions, about 1 to 20, and preferably 5 to 15% by weight, of about one or more amide compound is used herein. The volume of the compositions of the present invention will comprise about 50 to 75, and preferably about 55 to 65 weight percent distilled water and about 10 to 40, and preferably about 15 to 30%, of a combination of other components cosmetically effective, commonly used auxiliaries of the various types of compositions in question (ie, lotion, cream, ointment, bar or soap). The auxiliary components chosen for use in said compositions must be chemically inert with respect to each other and with respect to the amide compounds of the present invention. The auxiliary components used in the compositions of the present invention, in addition to water, would include the following amounts of the following types of additives, in percent by weight, based on the total weight of the final composition: about 0.75 to 7.00% agents emulsifiers, approximately 3.00 to 15.00% of emollients, approximately 1.00 to 20.00% of medicament of the invention, approximately 0.10 to 5.00% of lubricant, approximately 0.20 to 1.00% of preservative, approximately 0.20 to 1.00% of perfume, approximately 0.01 to 0.10% of coloring, the rest, water. Lists of such materials, which are well known in the art, are described, for example in: "Cos etics: Science and Technology", edited by M. S. Balsam and E. Sagarin, 2a. edition, 1972, Wiley Publ. Co.; "The Chemistry and Manufacture of Cosmetics", by M. G.

DeNavasse; and "Harry's Cosmeticology", J. B: ilkinson and coauthors, 7a. edition, 1982, Che. Pu. Co. The amide compounds, in themselves, can be applied topically in an uncomplexed form, to the areas of the skin to be treated with them. Whether used as they are, or in the form of compounds or compositions, for purposes of treating dry pei, the amide compounds of the present invention are topically applied one or more, and preferably about 2 to 4 times daily, to the area of the skin that is going to be treated with them, for a period of about 7 to 21 days, in order to obtain the desired improvement of the dry skin condition.

The compounds of the present invention can be stored as they are or in the form of the compositions described herein, in closed containers at room temperature, for extended periods, without a change in their usefulness for treatment of dry skin. The amide compounds and the amide-containing compositions of the present invention are not irritating to the skin, are not allergenic or toxic. The following examples are merely illustrative of the present invention and are not intended to limit its scope. EXAMPLE 1 Glucono-delta-lactone (352 g) was heated in 1000 ml. of isopropyl alcohol at reflux temperatures, about 86 ° C (at atmospheric pressure) in a two-liter, three-neck glass flask equipped with a stirrer, a reflux condenser column and a plug inlet protrusion. Then 180g of methoxypropylamine was added to the lactone suspension at reflux, over a period of about 10 minutes, through the entry port. The resulting system was then stirred and heated to reflux (86 ° C) for an additional 10 minutes, and then the heat was turned off. At this temperature (approximately 86 ° C), all the components of the system were dissolved in the isopropyl alcohol. When the system cooled, a precipitate began to form at approximately 65 ° C. When the temperature of the system reached room temperature (approximately 25 ° C), the system was filtered through a Buchner funnel, under vacuum (domestic) and the filtrate was recovered.The solid was transferred to a pyrex dish to dry at room temperature. air (more than about 6 hours).

Thus, a yield of 510 g of product was obtained (methoxypropylgluconamide) for a yield of 95.86% of theory. An additional quantity of said product was also obtained, 12 g, after distilling off about 90% of the isopropyl alcohol from the filtrate passing through the filter. The two portions of recovered solids were mixed together and approximately 100 g of the solids thus recovered were recrystallized in water and isopropyl alcohol. An analysis of said product showed that it contained 5.17% nitrogen, compared to 5.18% of theory. The compound had a melting point of 107.5 ° C. the infrared spectrum of the moatro compound sink aiguii ieu i vuu to 3500, 3400, 3340, 2920, 2880, 1650, 1535, 1430, 1240, 1180, 1095, 1070, 1035, 730 and 630 reciprocal centimeters (cm). These bands are characteristics of hydroxy stretching, 1G Nitrogen-hydrogen stretching, methyl stretching, methoxy stretching and several secondary amide bands. EXAMPLES 2 TO 3 or component weight Component Water 70.36 70.36 Propylene glycol 1.00 1.00 methyl p-hydroxybenzoate 0.30 0.30 Mineral oil 1.50 1.50 Alcoholic benzoate of Ci _ g 1.50 1.50 Glyceryl monostearate 2.30 2.30 Polawax * 4.08 4.08 Stearyl alcohol 1.50 1.50 Stearilic ether of polyoxie i log 0.75 0.75 Silicone oil 0.21 0.21 Steararoi stearyl stearate 1.00 1.00 propyl p-hydroxybenzoate 0.10 0.10 Bisabolol 0.20 0.20 Imidazolidinylurea 0.20 0.20 Metoxipropylgluconamide 15.00 Glucono-delta-lactone 15.00 TOTAL 100.00 100.00 * Polawax (Croda, Inc. ) is a preparation of higher fatty alcohols and reaction products of ethyl oxide. Both emulsions were prepared from four (4) subcombinations, or phases, of the components listed above. Phase A is made of 52.36% water, 1.00% propylene glycol and 0.30% methyl p-hydroxybenzoate. Phase D is made of 15.00% water and 15.00% of the additive that is being evaluated comparatively, that is, methoxypropylgluconamide or glucono-delta-lactone. Phase B contains all the remaining components, except imidazolidinylurea. The components of phase A are mixed together first by heating to 82 ° C and the components of phase B are also mixed together at 80 ° C. Phase B is then added to phase A and heating is continued (a 80 ° C) and mixing for about 10 minutes, then the heating is stopped Phase C is formed by dissolving the imidazolidinylurea in the water and heating to 5 ° C. Phase C is then added to the mixture of phases A / B. Phase D is made by dissolving the selected additive in water and heating to 45 ° C, then phase D is added to the mixture of A / B / C phases. The resulting product is then cooled to 35 ° C by mixing and packing.

The formulations of Examples 2 to 3 were comparatively evaluated by a panel test of 10 panelists with dry skin. In evading the test formulations, the istua panel cleaned their forearms with their regular soap once in the morning and once in the afternoon, and then applied the test formulation to a forearm. The other forearm was left untreated, as a control. Thus, each formulation was tested twice daily for a period of two weeks. At the end of this time, the forearms of each panel were compared. The results showed that, although the formulation of Example 2 provided some improvement of the dry skin condition of the treantized forearms, compared to the untreated forearms, the use of the formulation of Example 3 provided a markedly improved difference in its effect on the dry skin of the forearms treated with it, in comparison with the effect provided by the use of the formulation of example 2 EXAMPLE 4 This example illustrates the compatibility of methoxypropylgluconamide with other cosmetic ingredients, including sunscreen agents. Component% by weight »Water 62.125 Methylparaben 0: 250 Propylene glycol 5.000 Carbomer 941 0.125 Triethanolamine 0.100 Glyceryl stearate and Laureth-23 (polysxyethylene ether) 8,000 Cetilic alcohol 1,500 Methylparaben 0.150 Butylated hydroxyanisole 0.150 Alcoholic benzoate of n-j-i? 5,000 Ethylhexyl oxysterate 1-1 inoleoi lo 5,000 Bisabolol 0.200 Glycol stearate 3.000 Dimethicone 1,000 Stereoaryl ether of polyoxyethylene wood 21 0.750 Octildimethyl-PABA 3,000 Benzof nona-3 1,500 Dimetilol-dimeti lhidanto i at 0. 00 Perfume • 0.0.250 Methoxypropylgluconamide 2,500 TOTAL 100.000 Methoxypropylgluconamide was physically, chemically and functionally compatible with the other components of the formulation of Example 4. The use of methoxypropylgluconamide in the formulation of Example 4 provides markedly improved dry skin treatment properties, as compared to the use of the same formulation without said amide in it. The formulation is also useful for sunlight filtration purposes. EXAMPLE 5 The following illustrates the compatibility of the present amide compound in a water-in-oil emulsion formulation.

Component% by weight Water 52,058 Metilparab? N 0.200 Ethylparabon 0.150 Disodium salt of ethylenediaminetetraacetic acid 0.240 Butylated hydroxyanisole 0.150 Propylene glycol 4.000 Triethanolamine 0.092 Cyclomethicone 10,000 Carpobol 1342 (Carbomer 1342) 0.110 Dimethicone 50 is 10,000 dimethicone 1000 is 7,500 Isocetine oxyethate 1-1 inoleoi lo 5,000 * Abil WS08 5,000 Phenoxyethanol 0.500 Me toxiprcpi lgluconamide 5,000 TOTAL 100.00

Claims (3)

* Abil WS08 (Goldschmidt AG) is a combination of cetyldimethicone, copolol iol-cethi ldimethicone, oleate of ig igeri lo-3 and hexyl laurate. Methoxypropylgluconamide was physically, "chemically and functionally compatible with the other components of the formulation of Example 5. The use of methoxypropylgluconamide in the formulation of Example 5 provides remarkably improved dry skin treatment properties, as compared to the use, for purposes, of the same formulations, without said amide in them CLAIMS 1. In a process for moisturizing the human skin by means of the application to it of a composition adapted to provide such treatment, the improvement that comprises using said composition or compound , at least, a compound that has the structure:
1. HO-CH2- (CHOH) -0- (CmH2m + 1) wherein p is an integer from 1 to 4, (CnH2n) is a straight or branched chain alkyl bridge in which n is an integer of 1 to 6,, (CmH2m + 1) is a straight or branched chain alkyl group in which m is an integer from 1 to 6, as a wetting and softening active agent.
2. 2. In a process for moisturizing and softening the human skin by means of applying to it a composition or compound adapted to provide said treatment, the. improvement comprising employing as said composition or compound at least one compound of claim 1, wherein p is 4, as a wetting and softening active agent.
3. 3. In a process for moisturizing and softening the human skin by means of applying it to a composition or compound adapted to provide said treatment, the improvement comprising employing as said composition or compound, at least one compound of the claim 1, wherein m is 1, as a wetting and softening active agent. IN WITNESS WHEREOVER, I sign the above in this city of Mexico, D. F., on the 21st day of the month of April of 1989. BY REVLON, INC. C