MXPA94005923A - Improvements in process to smoke and soften p - Google Patents
Improvements in process to smoke and soften pInfo
- Publication number
- MXPA94005923A MXPA94005923A MXPA/A/1994/005923A MX9405923A MXPA94005923A MX PA94005923 A MXPA94005923 A MX PA94005923A MX 9405923 A MX9405923 A MX 9405923A MX PA94005923 A MXPA94005923 A MX PA94005923A
- Authority
- MX
- Mexico
- Prior art keywords
- compound
- composition
- skin
- treatment
- softening
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 239000000779 smoke Substances 0.000 title 1
- 210000003491 Skin Anatomy 0.000 claims abstract description 19
- 230000003020 moisturizing Effects 0.000 claims abstract description 7
- 239000000203 mixture Substances 0.000 claims description 43
- 150000001875 compounds Chemical class 0.000 claims description 19
- 206010013786 Dry skin Diseases 0.000 claims description 18
- 230000037336 dry skin Effects 0.000 claims description 18
- 238000009472 formulation Methods 0.000 claims description 12
- HNDZVVPAHINRHT-BDNRQGISSA-N COCCC[C@](O)(C(N)=O)[C@@H](O)[C@H](O)[C@H](O)CO Chemical compound COCCC[C@](O)(C(N)=O)[C@@H](O)[C@H](O)[C@H](O)CO HNDZVVPAHINRHT-BDNRQGISSA-N 0.000 claims description 8
- 150000001408 amides Chemical class 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 238000009736 wetting Methods 0.000 claims 3
- 229940085262 Cetyl dimethicone Drugs 0.000 claims 1
- 229940049964 Oleate Drugs 0.000 claims 1
- CMBYOWLFQAFZCP-UHFFFAOYSA-N hexyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCCCCCC CMBYOWLFQAFZCP-UHFFFAOYSA-N 0.000 claims 1
- 229940100463 hexyl laurate Drugs 0.000 claims 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-M oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC([O-])=O ZQPPMHVWECSIRJ-KTKRTIGZSA-M 0.000 claims 1
- 150000001261 hydroxy acids Chemical class 0.000 abstract description 3
- 238000009499 grossing Methods 0.000 abstract 1
- -1 amide compound Chemical class 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 238000010992 reflux Methods 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 8
- 210000000245 Forearm Anatomy 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- LXCFILQKKLGQFO-UHFFFAOYSA-N Methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 150000002596 lactones Chemical class 0.000 description 5
- PHOQVHQSTUBQQK-SQOUGZDYSA-N Glucono δ-lactone Chemical group OC[C@H]1OC(=O)[C@H](O)[C@@H](O)[C@@H]1O PHOQVHQSTUBQQK-SQOUGZDYSA-N 0.000 description 4
- 229960003681 Gluconolactone Drugs 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 235000012209 glucono delta-lactone Nutrition 0.000 description 4
- 239000000182 glucono-delta-lactone Substances 0.000 description 4
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 4
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- UQEAIHBTYFGYIE-UHFFFAOYSA-N Hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 230000001476 alcoholic Effects 0.000 description 3
- 230000004075 alteration Effects 0.000 description 3
- 238000005336 cracking Methods 0.000 description 3
- 239000006071 cream Substances 0.000 description 3
- 229940008099 dimethicone Drugs 0.000 description 3
- 239000004205 dimethyl polysiloxane Substances 0.000 description 3
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- ZCTXEAQXZGPWFG-UHFFFAOYSA-N imidurea Chemical compound O=C1NC(=O)N(CO)C1NC(=O)NCNC(=O)NC1C(=O)NC(=O)N1CO ZCTXEAQXZGPWFG-UHFFFAOYSA-N 0.000 description 3
- 239000006210 lotion Substances 0.000 description 3
- 239000002674 ointment Substances 0.000 description 3
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 3
- 239000000344 soap Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 230000000699 topical Effects 0.000 description 3
- WLAMNBDJUVNPJU-UHFFFAOYSA-N 2-methylbutyric acid Chemical compound CCC(C)C(O)=O WLAMNBDJUVNPJU-UHFFFAOYSA-N 0.000 description 2
- RGZSQWQPBWRIAQ-CABCVRRESA-N Bisabolol Chemical compound CC(C)=CCC[C@](C)(O)[C@H]1CCC(C)=CC1 RGZSQWQPBWRIAQ-CABCVRRESA-N 0.000 description 2
- 229940043253 Butylated Hydroxyanisole Drugs 0.000 description 2
- CZBZUDVBLSSABA-UHFFFAOYSA-N Butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 2
- 239000004255 Butylated hydroxyanisole Substances 0.000 description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-N Gluconic acid Chemical group OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
- 206010040844 Skin exfoliation Diseases 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Tris Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000000996 additive Effects 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-M benzoate Chemical compound [O-]C(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-M 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229940036350 bisabolol Drugs 0.000 description 2
- 229930000006 bisabolols Natural products 0.000 description 2
- 235000019282 butylated hydroxyanisole Nutrition 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000004299 exfoliation Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 229950004594 levomenol Drugs 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229960002216 methylparaben Drugs 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- VBICKXHEKHSIBG-UHFFFAOYSA-N rac-1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- FAXDZWQIWUSWJH-UHFFFAOYSA-N 3-methoxypropan-1-amine Chemical compound COCCCN FAXDZWQIWUSWJH-UHFFFAOYSA-N 0.000 description 1
- 206010000496 Acne Diseases 0.000 description 1
- 229940075509 Carbomer 1342 Drugs 0.000 description 1
- 206010012444 Dermatitis diaper Diseases 0.000 description 1
- 208000003105 Diaper Rash Diseases 0.000 description 1
- 229940100242 Glycol Stearate Drugs 0.000 description 1
- RFVNOJDQRGSOEL-UHFFFAOYSA-N Glycol stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCO RFVNOJDQRGSOEL-UHFFFAOYSA-N 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 206010020649 Hyperkeratosis Diseases 0.000 description 1
- 206010021198 Ichthyosis Diseases 0.000 description 1
- 206010021197 Ichthyosis Diseases 0.000 description 1
- 208000001126 Keratosis Diseases 0.000 description 1
- 229940100556 Laureth-23 Drugs 0.000 description 1
- 239000004264 Petrolatum Substances 0.000 description 1
- 229940066842 Petrolatum Drugs 0.000 description 1
- QCDWFXQBSFUVSP-UHFFFAOYSA-N Phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
- 229960005323 Phenoxyethanol Drugs 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- QELSKZZBTMNZEB-UHFFFAOYSA-N Propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- 208000008742 Seborrheic Dermatitis Diseases 0.000 description 1
- 206010039792 Seborrhoea Diseases 0.000 description 1
- GLDOVTGHNKAZLK-UHFFFAOYSA-N Stearyl alcohol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 1
- 206010042496 Sunburn Diseases 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 230000002009 allergen Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- SHHIADHOJKLUIZ-UHFFFAOYSA-N azane;molecular hydrogen Chemical compound N.[H][H] SHHIADHOJKLUIZ-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000008406 cosmetic ingredient Substances 0.000 description 1
- 229940086555 cyclomethicone Drugs 0.000 description 1
- 230000001809 detectable Effects 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N edta Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 239000003974 emollient agent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 229950006191 gluconic acid Drugs 0.000 description 1
- 229940075507 glyceryl monostearate Drugs 0.000 description 1
- 229940075529 glyceryl stearate Drugs 0.000 description 1
- 239000008311 hydrophilic ointment Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- NKBWPOSQERPBFI-UHFFFAOYSA-N octadecyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCCCC NKBWPOSQERPBFI-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N p-acetaminophenol Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 229920000059 polyethylene glycol stearate Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002335 preservative Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 201000004681 psoriasis Diseases 0.000 description 1
- 239000005297 pyrex Substances 0.000 description 1
- 150000003334 secondary amides Chemical class 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000000516 sunscreening agent Substances 0.000 description 1
- 230000001225 therapeutic Effects 0.000 description 1
- 230000002588 toxic Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
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)
- 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. 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. 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
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US18485888A | 1988-04-22 | 1988-04-22 | |
US184858 | 1988-04-22 |
Publications (2)
Publication Number | Publication Date |
---|---|
MX9405923A MX9405923A (en) | 1998-07-31 |
MXPA94005923A true MXPA94005923A (en) | 1998-11-09 |
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