US3689668A - Method of alleviating wrinkles on skin - Google Patents
Method of alleviating wrinkles on skin Download PDFInfo
- Publication number
- US3689668A US3689668A US80492A US3689668DA US3689668A US 3689668 A US3689668 A US 3689668A US 80492 A US80492 A US 80492A US 3689668D A US3689668D A US 3689668DA US 3689668 A US3689668 A US 3689668A
- Authority
- US
- United States
- Prior art keywords
- arginine
- diethylaminoethanol
- para
- compound
- aminobenzoyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title claims abstract description 36
- 230000037303 wrinkles Effects 0.000 title abstract description 22
- 239000000203 mixture Substances 0.000 claims abstract description 46
- 239000004475 Arginine Substances 0.000 claims abstract description 34
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims abstract description 29
- 150000001875 compounds Chemical class 0.000 claims description 39
- 229940009098 aspartate Drugs 0.000 claims description 26
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 239000004615 ingredient Substances 0.000 claims description 6
- 230000000887 hydrating effect Effects 0.000 abstract description 32
- 239000002537 cosmetic Substances 0.000 abstract description 15
- 150000001412 amines Chemical class 0.000 abstract description 3
- 229960003121 arginine Drugs 0.000 description 28
- 239000006071 cream Substances 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- -1 amine compounds Chemical class 0.000 description 13
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 12
- 238000009472 formulation Methods 0.000 description 12
- 210000004381 amniotic fluid Anatomy 0.000 description 10
- 239000012153 distilled water Substances 0.000 description 10
- 239000004480 active ingredient Substances 0.000 description 8
- 239000000284 extract Substances 0.000 description 8
- 238000011282 treatment Methods 0.000 description 8
- 210000002826 placenta Anatomy 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 239000001763 2-hydroxyethyl(trimethyl)azanium Substances 0.000 description 5
- 235000019743 Choline chloride Nutrition 0.000 description 5
- 235000021355 Stearic acid Nutrition 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- SGMZJAMFUVOLNK-UHFFFAOYSA-M choline chloride Chemical compound [Cl-].C[N+](C)(C)CCO SGMZJAMFUVOLNK-UHFFFAOYSA-M 0.000 description 5
- 229960003178 choline chloride Drugs 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 210000001061 forehead Anatomy 0.000 description 5
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 4
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- 229930195712 glutamate Natural products 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 229920000151 polyglycol Polymers 0.000 description 4
- 239000010695 polyglycol Substances 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N squalane Chemical compound CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- AELUALNOBYDJNF-UHFFFAOYSA-N 3-amino-2-(diethylamino)-2-hydroxy-1-phenylpropan-1-one Chemical compound NCC(O)(N(CC)CC)C(C1=CC=CC=C1)=O AELUALNOBYDJNF-UHFFFAOYSA-N 0.000 description 3
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 description 3
- 235000021314 Palmitic acid Nutrition 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000000443 aerosol Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 150000002191 fatty alcohols Chemical class 0.000 description 3
- 235000013336 milk Nutrition 0.000 description 3
- 239000008267 milk Substances 0.000 description 3
- 210000004080 milk Anatomy 0.000 description 3
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 3
- 239000003755 preservative agent Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 230000001153 anti-wrinkle effect Effects 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 229940057995 liquid paraffin Drugs 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
- 229920000053 polysorbate 80 Polymers 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- DSEKYWAQQVUQTP-XEWMWGOFSA-N (2r,4r,4as,6as,6as,6br,8ar,12ar,14as,14bs)-2-hydroxy-4,4a,6a,6b,8a,11,11,14a-octamethyl-2,4,5,6,6a,7,8,9,10,12,12a,13,14,14b-tetradecahydro-1h-picen-3-one Chemical compound C([C@H]1[C@]2(C)CC[C@@]34C)C(C)(C)CC[C@]1(C)CC[C@]2(C)[C@H]4CC[C@@]1(C)[C@H]3C[C@@H](O)C(=O)[C@@H]1C DSEKYWAQQVUQTP-XEWMWGOFSA-N 0.000 description 1
- 150000000218 1-tetradecanols Chemical class 0.000 description 1
- LEACJMVNYZDSKR-UHFFFAOYSA-N 2-octyldodecan-1-ol Chemical compound CCCCCCCCCCC(CO)CCCCCCCC LEACJMVNYZDSKR-UHFFFAOYSA-N 0.000 description 1
- GFJRUFUABGJGMR-UHFFFAOYSA-N 3-ethyltetradecan-3-ol Chemical compound CCCCCCCCCCCC(O)(CC)CC GFJRUFUABGJGMR-UHFFFAOYSA-N 0.000 description 1
- LIFHMKCDDVTICL-UHFFFAOYSA-N 6-(chloromethyl)phenanthridine Chemical compound C1=CC=C2C(CCl)=NC3=CC=CC=C3C2=C1 LIFHMKCDDVTICL-UHFFFAOYSA-N 0.000 description 1
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- 239000004338 Dichlorodifluoromethane Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- NWGKJDSIEKMTRX-BFWOXRRGSA-N [(2r)-2-[(3r,4s)-3,4-dihydroxyoxolan-2-yl]-2-hydroxyethyl] (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](O)C1OC[C@H](O)[C@H]1O NWGKJDSIEKMTRX-BFWOXRRGSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical class COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 1
- 230000003064 anti-oxidating effect Effects 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- BTFJIXJJCSYFAL-UHFFFAOYSA-N arachidyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCO BTFJIXJJCSYFAL-UHFFFAOYSA-N 0.000 description 1
- 229960002223 arginine aspartate Drugs 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- 229940095259 butylated hydroxytoluene Drugs 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- SASYSVUEVMOWPL-NXVVXOECSA-N decyl oleate Chemical compound CCCCCCCCCCOC(=O)CCCCCCC\C=C/CCCCCCCC SASYSVUEVMOWPL-NXVVXOECSA-N 0.000 description 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- YOBAEOGBNPPUQV-UHFFFAOYSA-N iron;trihydrate Chemical compound O.O.O.[Fe].[Fe] YOBAEOGBNPPUQV-UHFFFAOYSA-N 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- 239000012184 mineral wax Substances 0.000 description 1
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 1
- 235000010935 mono and diglycerides of fatty acids Nutrition 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 210000002381 plasma Anatomy 0.000 description 1
- 229940052795 plexion Drugs 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 229940068968 polysorbate 80 Drugs 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 239000007944 soluble tablet Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- IHCDKJZZFOUARO-UHFFFAOYSA-M sulfacetamide sodium Chemical compound O.[Na+].CC(=O)[N-]S(=O)(=O)C1=CC=C(N)C=C1 IHCDKJZZFOUARO-UHFFFAOYSA-M 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 208000001644 thecoma Diseases 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 229940045860 white wax Drugs 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
- A61K8/98—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution of animal origin
- A61K8/981—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution of animal origin of mammals or bird
- A61K8/982—Reproductive organs; Embryos, Eggs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/08—Anti-ageing preparations
Definitions
- ABSTRACT Cosmetic compositions containing an amine, such as the di-aspartate of arginine para-aminobenzoyldiethylaminoethanol, and a method for the substantial reduction of folds and wrinkles in the skin are disclosed.
- the cosmetic compositions are useful in that they have a hydrating effect on the human skin such that the complexion and brightness thereof can be substantially improved, whereas the folds and wrinkles of the skin can be substantially reduced.
- the compounds of the general formula I m y be can be substantially reduced by applying the cosmetic prepared by reaction of one or two moles of arginine compositions to the human skin. glutamate or aspartate with one mole of para- 2.
- This invention relates to cosmetic compositions hav- EXAMPLE 1 ing a significant hydrating activity when topically applied to human skin, due to the presence in the To 46.82 grams of dry (l) arginine di-( l+) glutacosmetic compositions of amine compounds as defined mate dissolved in 500 millilitres of fresh distilled water, hereafter which have a hydrating activity which was h d at 80 C, 2353 grams f i b lunknown heretofore and which have not been used in diethylaminoethanol are added, while stirring.
- the mixture is maintained at the boiling temperature also be added to known hydrating cosmetic composi- C) under d d r ss re and is then conliOnS, in which hey increase surprisingly the hydrating centrated, by distillation of the aqueous solvent, until activity of the known hydrating ihgfedlehtsan opalescent product is obtained.
- the product is then crystallized at a temperature of less than 0 C and dried SUMMARY OF THE INVENTION during 24 hours at 45 C in a drying closet.
- the invention concerns a method for substantially Yi ld; 98 t 99%.
- Cosmetic compositions Containing, as aminobenzoyl-diethylaminoethanol are thus obactive ingredient, at least one amine compound, which 45 mi d may be represented by the following general formula: Melting P i t; 172 173 C NH C2115 o I 0OOH-HzN-il-NH-(CHz)sCHNHzCOOH COOH-lh-(CHQPOil-Q-Nflt 1 (52115 [en-N112 ()HNH2 A 9 a *B s9, 1 (I) in which R represents an alkylene group -(Cll..),, EXAMPLEZ where n l or 2, and m represents 1 or 2.
- EXAMPLE 3 To a boiling solution of 44 grams of dry (1) arginine di-(l-) aspartate in 500 millilitres of fresh distilled water, 23.63 grams of para-aminobenzoyldiethylaminoethanol are added while stirring. The reaction mixture is then treated as described in Example l. About 66 grams of crystalline di-( l--) aspartate of l) arginine diethylaminoethanol are obtained.
- EXAMPLE 6 100 milliliters of a 1N solution of hydrochloric acid are added to 44 grams of (l) arginine di (l) aspartate. The obtained solution is heated to boiling tem-- perature and 400 milliliters of fresh distilled water are added thereto. While maintaining the temperature at 85 C and while stirring the mixture, 23.63 grams of para-aminobenzoyldiethylaminoethanol are added. The reaction mixture is then treated as described in Example l. About 70 grams of crystalline monohydrochloride of di(1) asparate of l)arginine para-aminobenzoyl-diethylaminoethanol are obtained.
- EXAMPLE 7 The tri-glutamate of di-arginine para-aminobenzoyldiethylaminoethanol (M.P.: 235-238 C) and the hydrochloride thereof are prepared by the procedure described in Examples 1, 2 and 3, except that two moles of di-arginine glutamate per mole of paraaminobenzoyl-diethylaminoethanol are used.
- EXAMPLE 8 The tri-aspartate of di-arginine para-aminobenzoyldiethylaminoethanol (M.P.: 205208 C) and the hydrochloride thereof are prepared by the procedure described in Examples 4, 5 and 6, except that two moles of di-arginine aspartate per mole of parapara-aminobenzoylaminobenzoyl-diethylaminoethano1 are used. 1
- the compounds of the general formula 1 and the hydrochlorides thereof are soluble in water. All that is necessary is to apply topically the compounds of the general formula I in an effective amount of the compound sufficient to alleviate the folds and wrinkles of the skin.
- compositions for external use according to this invention may take various forms and may be used on the human skin.
- Said compositions may take the form of fatty or non fatty creams, milky suspensions or emulsions of the water-in-oil or oil-in-water types, lotions, gels or jellies, colloidal or non colloidal aqueous or oily solutions, pastes, soaps, aerosols, soluble tablets (to be dissolved in a fluid, such as water) or sticks.
- the amount of active ingredient contained in the hydrating cosmetic compositions according to the invention applied to the skin may vary between wide limits, depending from the formulating and from the frequency of use of said compositions. Generally, said compositions contain from 0.1% to 2%, by weight of the composition of active ingredient of the formula 1.
- the hydrating cosmetic compositions used in the method according to the invention may contain not only one or more active ingredients of the formula 1 but also conventional vehicles or carriers, such as solvents, fats, oils and mineral waxes, fatty acids and derivatives thereof, alcohols and derivatives thereof, glycols and derivatives thereof, glycerol and derivatives thereof, sorbitol and derivatives thereof, surface-active agents of the anionic, cationic or non ionic type, emulsifying agents, preserving agents, perfumes, etc.
- conventional vehicles or carriers such as solvents, fats, oils and mineral waxes, fatty acids and derivatives thereof, alcohols and derivatives thereof, glycols and derivatives thereof, glycerol and derivatives thereof, sorbitol and derivatives thereof, surface-active agents of the anionic, cationic or non ionic type, emulsifying agents, preserving agents, perfumes, etc.
- EXAMPLE 1 Hydrating Milk Mono and diglycerides of fatty acids 5 to 6% (palmitic and stearic acids) Condensate of polyglycol and saturated 2.5 to 3% fatty alcohol ethers with polyoxyethylene lsopropyleneglycol 5 to 15% Perhydrosqualene 5 to 15% Amniotic fluid 2 to 10% Tri-aspartate of di-arginine-paraaminobenzoyl diethylaminoethanol 0.5 to 1% Distilled water q.s.ad.
- EXAMPLE ll Hydrating Milk High fatty alcohols such as cetyl, stearyl, myristyl alcohols
- Tri-aspartate of di-arginine-paraaminobenzoyl-diethylaminoethanol 0.5 to 1% Distilled water q.s.ad.
- dyes or pigments such as zinc oxide, titanium oxide, ochre and the like
- preserving or antioxidizing agents such as butylhydroxy toluene, butylhydroxy ariisole, sorbic acid, methyl para-hydroxybenzoate, and the like
- the tests have been made by applying on the human face (forehead and cheeks) masks for taking impressions of the relief of the skin before and after treatment by means of various hydrating compositions.
- compositions of the Laboratory of Dr. Renaux (Paris, France) containing rubber or plastic materials, which cure in contact with the skin have been used.
- the masks obtained after curing or hardening on the face of the rubber or plastic-based compositions and after removing the hardened layers from the face may be used for determining objectively the effectiveness of the hydrating compositions acco rding to the invention for reducing or alleviating the skin wrinkles, manly by hydrating the skin.
- the effect of reducing or alleviating the skin wrinkles is determined by counting with an approximation of il% the impressions of the wrinkles on surfaces of an area of 3cm ofthe masks.
- the count of impressions on the masks taken before the treatment by means of hydrating compositions is used as base for the subsequent counts.
- a value of is given to the number of wrinkle impressions counted on the mask taken before the treatment by means of the hydrating compositions.
- Said control cream had the following composition.
- Formulation A Monoand di-glycerides of palmitic and stearic acids 6% Condensate of polyglycol and saturated fatty alcohols with polyoxyethylene 3% Ester of stearic acid and diethyldodecanol 10% Preserving agent and perfume q.s.
- control cream A and the creams B to E were applied respectively on the lefthand part of the forehead or the lefthand cheek and on the righthand part of the forehead or righthand check.
- the patients were then treated, during 30 days, by means of the control cream (Formulation A) and by means of the cream (Formulation B) according to the invention.
- the anti-wrinkle effect of cream C is surprisingly increased of 18% and 19%, whereas the known active ingredients (amniotic fluid, placenta extract and choline chloride) have themselves, at the indicated doses, an anti-wrinkle effect which is substantially equivalent to that of the triaspartate of arginine para-aminobenzoyl diethylaminoethanol, as shown by a comparison of the results obtained with cream B (Table l) and cream C (Table 11) c.
- Third series of tests The procedure was the same as in the first series of tests, except that creams D and E were used and that the results were compared to those obtained with con-- trol cream A.
- a method of temporarily alleviating wrinkles on human skin which comprises topically applying to said skin a wrinkle alleviating effective amount of at least one compound of the formula:
Abstract
Cosmetic compositions containing an amine, such as the diaspartate of arginine para-aminobenzoyl-diethylaminoethanol, and a method for the substantial reduction of folds and wrinkles in the skin are disclosed. The cosmetic compositions are useful in that they have a hydrating effect on the human skin such that the complexion and brightness thereof can be substantially improved, whereas the folds and wrinkles of the skin can be substantially reduced.
Description
United States Paten Piette Sept. 5, 1972 [54] METHOD OF ALLEVIATING WRINKLES ON SKIN [72] Inventor: Emile Leon Piette, 40, Avenue Moliere, Brussels 18, Belgium 1968, abandoned.
[30] Foreign Application Priority Data Oct. 18, 1967 Belgium ..49740 [52] US. Cl. ..424/319, 424/105, 424/329 [51] Int. Cl. ..A6lk 7/00 [58] Field of Search ..424/319 [56] References Cited FOREIGN PATENTS OR APPLICATIONS 640,462 3/ 1964 Belgium OTHER PUBLICATIONS Chemical Abstracts, Vol. 63, p. 13415 (b), 1965.
Primary Examiner-Albert T. Meyers" Assistant Examiner -Doris J. Funderburk Attorney-Sughrue, Mion, Zinn & Macpeak [57] ABSTRACT Cosmetic compositions containing an amine, such as the di-aspartate of arginine para-aminobenzoyldiethylaminoethanol, and a method for the substantial reduction of folds and wrinkles in the skin are disclosed. The cosmetic compositions are useful in that they have a hydrating effect on the human skin such that the complexion and brightness thereof can be substantially improved, whereas the folds and wrinkles of the skin can be substantially reduced.
13 Claims, No Drawings METHOD OF ALLEVIATING WRINKLES ON SKIN When each R represents a methylene group Cl-l and m is 2, the compound of the general formu- CROSS'REFERENCE To RELATED la l is the tri-aspartate of di-L-arginine para- APPLICATIONS aminobenzoyl-diethylaminoethanol.
This application is a continuation of my co-pending 5 When each R represents an ethylene group -(CH application, Ser, No. 736,032, filed June 1 l, 1968 now and m is 2, the compound of the general formula I is abandoned. the tri-glutatmate of di-L-arginine para-aminobenzoyldiethylaminoethanole BACKGROUND OF THE INVENTION The compounds of the general formula I are crystal- 1, Fi ld f h I ti lizable and have similar physico-chemical and biologi- This invention relates to cosmetic compositions ha cal properties. They can be used in their dextrogyre ing such a hydrating effect on the human skin that the gy e o ace c o s a d also as complexion and brightness thereof can be substantially acid addition Salts, Such as the hydroehloridesimproved, whereas the folds and wrinkles of the skin The compounds of the general formula I m y be can be substantially reduced by applying the cosmetic prepared by reaction of one or two moles of arginine compositions to the human skin. glutamate or aspartate with one mole of para- 2. Description of the Prior Art aminobenzoyl-diethylamino-ethanol in a solvent, such The appearance of the skin depends from the comas distilled water, at the reflux boiling temperature of plexion, brightness, ruggedness (folds and wrinkles) the reaction medium. After evaporation under reduced and wear thereof. As is known, the relief of the skin pressure, the product is crystallized at a temperature of may be influenced by hydrating cosmetic compositions less than 0 C or is dried in a drying closet. Crystalline n g. as aetive ingredients, gly or Combmed, pure products, which are clearly distinguished from Various Products Such as extracts y tisues mere mixtures of the starting reactants, are thus obplacenta), animal Serums or plasmas, amniotic fluid, mi d i h i ld f98 t 99%, Plant eXtraetS, leeithines, amino-alcohols, Such as The preparation of the compounds of formula I is choline and the Sa ts a derivatives thereof, and the described with more details in the following examples. like.
This invention relates to cosmetic compositions hav- EXAMPLE 1 ing a significant hydrating activity when topically applied to human skin, due to the presence in the To 46.82 grams of dry (l) arginine di-( l+) glutacosmetic compositions of amine compounds as defined mate dissolved in 500 millilitres of fresh distilled water, hereafter which have a hydrating activity which was h d at 80 C, 2353 grams f i b lunknown heretofore and which have not been used in diethylaminoethanol are added, while stirring.
- cosmetology until now- The e amine comp n m y The mixture is maintained at the boiling temperature also be added to known hydrating cosmetic composi- C) under d d r ss re and is then conliOnS, in which hey increase surprisingly the hydrating centrated, by distillation of the aqueous solvent, until activity of the known hydrating ihgfedlehtsan opalescent product is obtained. The product is then crystallized at a temperature of less than 0 C and dried SUMMARY OF THE INVENTION during 24 hours at 45 C in a drying closet.
The invention concerns a method for substantially Yi ld; 98 t 99%. About 69 grams of crystalline direducing the folds and wrinkles in skin by topically ap- (1+) glutamate of (l) arginine para- P y hydrating Cosmetic compositions Containing, as aminobenzoyl-diethylaminoethanol are thus obactive ingredient, at least one amine compound, which 45 mi d may be represented by the following general formula: Melting P i t; 172 173 C NH C2115 o I 0OOH-HzN-il-NH-(CHz)sCHNHzCOOH COOH-lh-(CHQPOil-Q-Nflt 1 (52115 [en-N112 ()HNH2 A 9 a *B s9, 1 (I) in which R represents an alkylene group -(Cll..),, EXAMPLEZ where n l or 2, and m represents 1 or 2.
To a solution of 50.45 grams of the DETAILED DESCRIPTION OF THE INVENTION monohydrochloride of l) arginine di-( 1+) glutamate When each R in the above described formula dissolved in 450 millilitres of fresh distilled water, represents a methylene group (-Cl-l and m is l, heated at 80 C, 23.63 grams of para-aminobenzoylthe compound of the general formula I is the diaspardiethylaminoethanol are added, while stirring the reactate of arginine para-aminobenzoyltion medium. By treating this medium as described in diethylaminoethanol. Example 1. 72.5 grams of crystalline di-( 1+) glutamate When each R represents an ethylene group (Cl-l of l) arginine para-aminobenzoyland m is l, the compound of the general formula I is diethylaminoethanol are obtained. This compound the di-glutamate of arginine para-aminobenzoylstarts melting at 159 C with decomposition and melts diethylaminoethanol. until ll 72 C.
EXAMPLE 3 EXAMPLE 4 To a boiling solution of 44 grams of dry (1) arginine di-(l-) aspartate in 500 millilitres of fresh distilled water, 23.63 grams of para-aminobenzoyldiethylaminoethanol are added while stirring. The reaction mixture is then treated as described in Example l. About 66 grams of crystalline di-( l--) aspartate of l) arginine diethylaminoethanol are obtained.
Melting point: l44l48 C.
EXAMPLE 5 To a boiling solution of 47.65 grams of the monohydrochloride of l) arginine de (l)aspartate in 500 milliliters of fresh distilled water, 23.63 grams of para-aminobenzoyl-diethylaminoethanol are added while stirring. The reaction mixture is then treated as described in Example 1. About 70 grams of the crystalline monohydrochloride of di( 1) aspartate of l)arginine paraaminobenzoyl-diethylaminoethanol are obtained. This compound starts melting at 152 C (with decomposition).
EXAMPLE 6 100 milliliters of a 1N solution of hydrochloric acid are added to 44 grams of (l) arginine di (l) aspartate. The obtained solution is heated to boiling tem-- perature and 400 milliliters of fresh distilled water are added thereto. While maintaining the temperature at 85 C and while stirring the mixture, 23.63 grams of para-aminobenzoyldiethylaminoethanol are added. The reaction mixture is then treated as described in Example l. About 70 grams of crystalline monohydrochloride of di(1) asparate of l)arginine para-aminobenzoyl-diethylaminoethanol are obtained.
EXAMPLE 7 The tri-glutamate of di-arginine para-aminobenzoyldiethylaminoethanol (M.P.: 235-238 C) and the hydrochloride thereof are prepared by the procedure described in Examples 1, 2 and 3, except that two moles of di-arginine glutamate per mole of paraaminobenzoyl-diethylaminoethanol are used.
EXAMPLE 8 The tri-aspartate of di-arginine para-aminobenzoyldiethylaminoethanol (M.P.: 205208 C) and the hydrochloride thereof are prepared by the procedure described in Examples 4, 5 and 6, except that two moles of di-arginine aspartate per mole of parapara-aminobenzoylaminobenzoyl-diethylaminoethano1 are used. 1
The compounds of the general formula 1 and the hydrochlorides thereof are soluble in water. All that is necessary is to apply topically the compounds of the general formula I in an effective amount of the compound sufficient to alleviate the folds and wrinkles of the skin.
The hydrating cosmetic compositions for external use according to this invention, which contain, as active ingredients, at least one compound of formula 1, may take various forms and may be used on the human skin. Said compositions may take the form of fatty or non fatty creams, milky suspensions or emulsions of the water-in-oil or oil-in-water types, lotions, gels or jellies, colloidal or non colloidal aqueous or oily solutions, pastes, soaps, aerosols, soluble tablets (to be dissolved in a fluid, such as water) or sticks.
The amount of active ingredient contained in the hydrating cosmetic compositions according to the invention applied to the skin may vary between wide limits, depending from the formulating and from the frequency of use of said compositions. Generally, said compositions contain from 0.1% to 2%, by weight of the composition of active ingredient of the formula 1.
The hydrating cosmetic compositions used in the method according to the invention may contain not only one or more active ingredients of the formula 1 but also conventional vehicles or carriers, such as solvents, fats, oils and mineral waxes, fatty acids and derivatives thereof, alcohols and derivatives thereof, glycols and derivatives thereof, glycerol and derivatives thereof, sorbitol and derivatives thereof, surface-active agents of the anionic, cationic or non ionic type, emulsifying agents, preserving agents, perfumes, etc.
A few examples of hydrating cosmetic agents used in the method according to this invention are given hereafter. These examples are only illustrative and must not be considered as limiting the scope of the invention. In said examples, the percentages are by weight.
EXAMPLE 1 Hydrating Milk Mono and diglycerides of fatty acids 5 to 6% (palmitic and stearic acids) Condensate of polyglycol and saturated 2.5 to 3% fatty alcohol ethers with polyoxyethylene lsopropyleneglycol 5 to 15% Perhydrosqualene 5 to 15% Amniotic fluid 2 to 10% Tri-aspartate of di-arginine-paraaminobenzoyl diethylaminoethanol 0.5 to 1% Distilled water q.s.ad.
EXAMPLE ll Hydrating Milk High fatty alcohols (such as cetyl, stearyl, myristyl alcohols) 5 to 6% Condensate of polyglycol and saturated fatty alcohol ethers with polyoxyethylene 2.5 to 3% lsopropyleneglycol 5 to 15% Perhydrosqualene 5 to 15% Amniotic fluid 2 to 10% Tri-aspartate of di-arginine-paraaminobenzoyl-diethylaminoethanol 0.5 to 1% Distilled water q.s.ad. 100% EXAMPLE III Hydrating Milk Mono and diglycerides of palmitic and stearic acids to 6% Condensate of polyglycol and saturated fatty alcohol ethers with polyoxyethylene 2.5 to 3% Glycerol 5 to 15% Ester of stearic acid and octyldodecanol 5 to 15% Amniotic fluid 2 to Fri-glutamate of di-arginine paraaminobenzoyl diethylaminoethanol 0.5 to 1% Distilled water q.s.ad. 100% EXAMPLE IV Cream of the Oil-in-Water Type Liquid paraffin 40 to 60% White wax 5 to 10% Solid paraffin 2 to 8% Borax 0.1 to 0.5% Di-aspartate of arginine para-aminobenzoyl diethylaminoethanol 0.5 to 1% Distilled water q.s.ad. 100% EXAMPLE V Cream of the Water-in-Oil Type Liquid paraffin 30 to 50% Ozokerite 3 to 8% Solid paraffin l to 3% Lanoline 1.5 to 4% Mono-diglycerides of fat-forming fatty acids with not more than l/l00 of 1% butylated anisole, l/lOO of 1% butylated hydroxy toluene, and H100 of 1% citric acid in propylene glycol added as a preservative (Arlacel l86-Atlas Chemical Industries-Wilmington, Delaware, U.S.A.) l to 2% Polysorbate 80, an ester of sorbitan etherified with polyethylene glycol (Tween 80 Atlas Chemical Industries) 0.1 to 0.3% Di-glutamate of arginine paraaminobenzoyl-diethylaminoethanol 0.5 to 1% Water q.s.ad. 100% EXAMPLE VI Hydrating Lotion Triethanolamine lauryl sulfate 1 to 5% lsopropanol 40 to 60% Cetiol V (decylic ester of oleic acid- Dehydag Deutsche Hydrierwerke, Dusseldorf, Germany) 2 to 6% Triglutamate of di-arginine para-aminobenzoyl diethylaminoethanol 0.5 to 1% Water q.s.ad. 100% EXAMPLE VII Cream of the Water-in-Oil Type Amphoccrine K (Dehydag), a mixture of fatty alcohols and waxy esters of animal origin 40 to 60% Placenta extract 5 to Tri-aspartate of di-arginine paraaminobenzoyl diethylaminoethanol 0.5 to 1% Water q.s.ad. 100% EXAMPLE VIII Hydrating Aerosol The cream of the oil-in-water of Example IV and 8% by weight of a mixture of 40% dichlorodifluoromethane and 60% dichlorotetrafluoromethane are introduced into an aerosol container.
To the formulations described in Examples I to VIII,
like), dyes or pigments (such as zinc oxide, titanium oxide, ochre and the like), as well as preserving or antioxidizing agents (such as butylhydroxy toluene, butylhydroxy ariisole, sorbic acid, methyl para-hydroxybenzoate, and the like) may be added in suitable amounts, as well known in cosmetology.
Tests have been made in vivo with the hydrating cosmetic compositions according to the invention. These tests have clearly shown that said compositions have remarkable hydrating properties when topically applied to the skin.
These tests have shown the hydrating properties of the compounds of formula I as well as the synergistic effect of these compounds on already known hydrating products (such as amniotic fluid, placenta extract and the like), when they are used jointly with these known products.
The tests have been made by applying on the human face (forehead and cheeks) masks for taking impressions of the relief of the skin before and after treatment by means of various hydrating compositions. For taking such impressions, compositions of the Laboratory of Dr. Renaux (Paris, France) containing rubber or plastic materials, which cure in contact with the skin, have been used. The masks obtained after curing or hardening on the face of the rubber or plastic-based compositions and after removing the hardened layers from the face may be used for determining objectively the effectiveness of the hydrating compositions acco rding to the invention for reducing or alleviating the skin wrinkles, manly by hydrating the skin. The effect of reducing or alleviating the skin wrinkles is determined by counting with an approximation of il% the impressions of the wrinkles on surfaces of an area of 3cm ofthe masks.
The count of impressions on the masks taken before the treatment by means of hydrating compositions is used as base for the subsequent counts. A value of is given to the number of wrinkle impressions counted on the mask taken before the treatment by means of the hydrating compositions.
As control, a hydrating cream containing only water as the hydrating ingredient has been used.
Said control cream had the following composition.
Formulation A Monoand di-glycerides of palmitic and stearic acids 6% Condensate of polyglycol and saturated fatty alcohols with polyoxyethylene 3% Ester of stearic acid and diethyldodecanol 10% Preserving agent and perfume q.s.
Water q.s.ad. 100% For one series of tests, 1% of tri-aspartate of arginine para-aminobenzoyl-diethylaminoethanol (Formulation B) was added to said base or control cream.
For another series of tests, 20% of amniotic fluid, 10% of human placenta extract and 0.1% of choline chloride (Formulation C) was added to the control cream, these three known products being commonly used in hydrating creams of good quality.
For still another series of tests, 20% of amniotic fluid, 10% of human placenta extract, 0.1% of choline chloride and 1% of tri-aspartate of arginine paraaminobenzoyl-diethylaminoethanol (Formulation D) were added to the control cream.
Finally, for the last series of tests, a cream (Formulation E) similar to Formulation D was used, except that it contained 10% in place of 20% of amniotic fluid,
.in place of of placenta extract and 0.05% in place of 0.1% of choline chloride (i.e., 50% less of these active ingredients than in Formulation D), the proportion of tri-aspartate of arginine paraaminobenzoyldiethylaminoethanol remaining identical 1%).
The various tests were each made on fifteen 40 to 50 years old patients before and after daily treatments, in the evening, with the various creams (Formulations A to E) during 30 days, on the forehead or on the cheeks, of the patients.
The control cream A and the creams B to E were applied respectively on the lefthand part of the forehead or the lefthand cheek and on the righthand part of the forehead or righthand check.
a. First series of tests An impression of the face skin of patients was taken by means of a mask and the number of impressed wrinkles was counted. A value of 100% was given to the average of the total number of impressed wrinkles.
The patients were then treated, during 30 days, by means of the control cream (Formulation A) and by means of the cream (Formulation B) according to the invention.
After said treatment, a new impression of the'face of the 15 patients was taken and the number of remaining wrinkle impressions was counted. By taking the average number of remaining wrinkle impressions, the percentage of the remaining wrinkles was determined in comparison with the percentage 100%) determined before the treatment.
The following results were obtained:
TABLE 1 Treated Before After Treatment Skin Treatment Part Formula- Formulation A tion B Forehead 100% 90%(:1%) 49%(:1%) Cheeks 100% 45%(:1%)
cream A.
diethylaminoethanol to cream C, the anti-wrinkle effect of cream C is surprisingly increased of 18% and 19%, whereas the known active ingredients (amniotic fluid, placenta extract and choline chloride) have themselves, at the indicated doses, an anti-wrinkle effect which is substantially equivalent to that of the triaspartate of arginine para-aminobenzoyl diethylaminoethanol, as shown by a comparison of the results obtained with cream B (Table l) and cream C (Table 11) c. Third series of tests The procedure was the same as in the first series of tests, except that creams D and E were used and that the results were compared to those obtained with con-- trol cream A.
These results are given in the following table:
tri-aspartate of arginine para-aminobenzoyl diethylaminoethanol on conventional ingredients (amniotic fluid, placenta extract and choline chloride), since the results obtained when the percentage of these three known active ingredients is reduced by 50% and when the percentage (1%) of the above tri-aspartate is maintained are nearly the same and even slightly better than the. results obtained with a twofold percentage of these three active ingredients.
Tests made with hydrating compositions containing other compounds of the formula I have given similar results.
What is claimed is:
l. A method of temporarily alleviating wrinkles on human skin, which comprises topically applying to said skin a wrinkle alleviating effective amount of at least one compound of the formula:
in which R represents an alkylene group (Cl-l wherein n=1 or 2, and m represents 1 or 2, or the acid addition salt thereof.
2. The method of claim 1 wherein the compound is the di-aspartate of arginine para-aminobenzoyldiethylaminoethanol.
3. The method of claim 1 wherein the compound is an acid addition salt of the di-aspartate of arginine para-aminobenzoyl-diethylaminoethanol.
4. The method of claim 1 wherein the compound is the hydrochloride of di-aspartate of arginine paraaminobenzoyl-diethylaminoethanol. v
5. The method of claim 1 wherein the compound is the di-glutamate of arginine para-aminobenzoyldiethylaminoethanol.
6. The method of claim 1 wherein the compound is the hydrochloride of di-glutamate of arginine paraaminobenzoyl-diethylaminoethanol.
7. The method of claim 1 wherein the compound is the tri-aspartate of di-L-arginine para-aminobenzoyldiethylaminoethanol.
8. The method of claim 1 wherein the compound is an acid addition salt of the tri-aspartate of di-L-arginine para-aminobenzoyl-diethylaminoethanol.
9. The method of claim 1 wherein the compound is the hydrochloride of tri-aspartate of di-L-arginine paraaminobenzoyl-diethylaminoethanol.
10. The method of claim 1 wherein the compound is the tri-glutamate of di-L-arginine-para-aminobenzoyldiethylaminoethanol.
11. The method of claim 1 wherein the compound is an acid addition salt of the tri-glutamate of di-L-arginine-para-aminobenzoyl-diethylaminoethanol.
12. The method of claim 1 wherein the ingredient is the hydrochloride of the tri-glutamate of di-L-argininepara-aminobenzoyl-diethylaminoethanol.
13. The method of claim 1 wherein the compound is contained in a cosmetically acceptable inert carrier at a level of from 0.1% to about 2% by weight of the composition. I I
Claims (12)
- 2. The method of claim 1 wherein the compound is the di-aspartate of arginine para-aminobenzoyl-diethylaminoethanol.
- 3. The method of claim 1 wherein the compound is an acid addition salt of the di-aspartate of arginine para-aminobenzoyl-diethylaminoethanol.
- 4. The method of claim 1 wherein the compound is the hydrochloride of di-aspartate of arginine para-aminobenzoyl-diethylaminoethanol.
- 5. The method of claim 1 wherein the compound is the di-glutamate of arginine para-aminobenzoyl-diethylaminoethanol.
- 6. The method of claim 1 wherein the compound is the hydrochloride of di-glutamate of arginine para-aminobenzoyl-diethylaminoethanol.
- 7. The method of claim 1 wherein the compound is the tri-aspartate of di-L-arginine para-aminobenzoyl-diethylaminoethanol.
- 8. The method of claim 1 wherein the compound is an acid addition salt of the tri-aspartate of di-L-arginine para-aminobenzoyl-diethylaminoethanol.
- 9. The method of claim 1 wherein the compound is the hydrochloride of tri-aspartate of di-L-arginine para-aminobenzoyl-diethylaminoethanol.
- 10. The method of claim 1 wherein the compound is the tri-glutamate of di-L-arginine-para-aminobenzoyl-diethylaminoethanol.
- 11. The method of claim 1 wherein the compound is an acid addition salt of the tri-glutamate of di-L-arginine-para-aminobenzoyl-diethylaminoethanol.
- 12. The method of claim 1 wherein the ingredient is the hydrochloride of the tri-glutamate of di-L-arginine-para-aminobenzoyl-diethylaminoethanol.
- 13. The method of claim 1 wherein the compound is contained in a cosmetically acceptable inert carrier at a level of from 0.1% to about 2% by weight of the composition.
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Cited By (18)
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---|---|---|---|---|
US5385938A (en) * | 1986-12-23 | 1995-01-31 | Yu; Ruey J. | Method of using glycolic acid for treating wrinkles |
US5389677A (en) * | 1986-12-23 | 1995-02-14 | Tristrata Inc | Method of treating wrinkles using glycalic acid |
US5554597A (en) * | 1986-12-23 | 1996-09-10 | Tristrata Inc | Compositions comprising 2-hydroxycarboxylic acids and related compounds, and methods for alleviating signs of dermatological aging |
US5665776A (en) * | 1986-12-23 | 1997-09-09 | Tristrata Technology, Inc. | Additives enhancing topical actions of therapeutic agents |
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US6191167B1 (en) | 1997-12-29 | 2001-02-20 | Tristrata Technology, Inc. | Pharmaceutical compositions containing hydroxycarboxylic acid and/or ketocarboxylic acids and methods of using the same |
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US8013017B2 (en) | 2001-05-31 | 2011-09-06 | Upsher-Smith Laboratories, Inc. | Dermatological compositions and methods |
US20170157015A1 (en) * | 2014-06-18 | 2017-06-08 | Medicell Technologies, Llc | Stem cell stimulating compositions and methods |
US10555897B1 (en) | 2013-03-16 | 2020-02-11 | Brahm Holdings Llc | Cosmetic composition and methods of treatment |
US11865142B2 (en) | 2016-03-23 | 2024-01-09 | Mimedx Group, Inc. | Compositions and methods of treatment with amniotic fluid |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE640462A (en) * | 1963-11-27 | 1964-03-16 |
-
1970
- 1970-10-13 US US80492A patent/US3689668A/en not_active Expired - Lifetime
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE640462A (en) * | 1963-11-27 | 1964-03-16 |
Non-Patent Citations (1)
Title |
---|
Chemical Abstracts, Vol. 63, p. 13415 (b), 1965. * |
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US5561159A (en) * | 1986-12-23 | 1996-10-01 | Tristrata Technology, Inc. | Method of treating wrinkles using tropic acid |
US5565487A (en) * | 1986-12-23 | 1996-10-15 | Tristrata, Inc. | Method of treating wrinkles using galactonic acid or galactonolactone |
US5571837A (en) * | 1986-12-23 | 1996-11-05 | Tristrata Technology Inc. | Method of treating wrinkles using saccharic acid or saccharolactone |
US5654340A (en) * | 1986-12-23 | 1997-08-05 | Tristrata Technology | Method of using gulonic acid or gulonolactone for treating wrinkles |
US5574067A (en) * | 1986-12-23 | 1996-11-12 | Tristrata Technology, Inc. | Method of treating wrinkles using gluconic acid or gluconolactone |
US5578644A (en) * | 1986-12-23 | 1996-11-26 | Tristrata Technology, Inc. | Method of treating wrinkles using isocitric acid |
US5580902A (en) * | 1986-12-23 | 1996-12-03 | Tristrata Technology, Inc. | Method of treating wrinkles using ethyl pyranate |
US5583156A (en) * | 1986-12-23 | 1996-12-10 | Tristrata Technology Inc. | Method of treating wrinkles using ribonic acid or ribonolactione |
US5589505A (en) * | 1986-12-23 | 1996-12-31 | Tristrata Technology, Inc. | Method of treating wrinkles using quinic acid or quinolactone |
US5656666A (en) * | 1986-12-23 | 1997-08-12 | Tristrata Technology, Inc. | Method of using ribonic acid or ribonolactone for treating wrinkles |
US5599843A (en) * | 1986-12-23 | 1997-02-04 | Tristrata Technology, Inc. | Method of treating wrinkles using 2-phenyllactic acid |
US5612376A (en) * | 1986-12-23 | 1997-03-18 | Tristrata Technology, Inc. | Method of treating wrinkles using 3-phenyllactic acid |
US5621006A (en) * | 1986-12-23 | 1997-04-15 | Yu; Ruey J. | Method for treating acne using benzilic acid |
US5643952A (en) * | 1986-12-23 | 1997-07-01 | Tristrata Technology, Inc. | Method of using 2-phenyllactic acid for treating wrinkles |
US5643962A (en) * | 1986-12-23 | 1997-07-01 | Tristrata Technology, Inc. | Method of using glucoleptonic acid for treating wrinkles |
US5643961A (en) * | 1986-12-23 | 1997-07-01 | Tristrata Technology, Inc. | Method of using malic acid for treating wrinkles |
US5643963A (en) * | 1986-12-23 | 1997-07-01 | Tristrata Technology, Inc. | Method of using isocitric acid for treating wrinkles |
US5643953A (en) * | 1986-12-23 | 1997-07-01 | Tristrata Technology | Method of using 3-phenyllactic acid for treating wrinkles |
US5648388A (en) * | 1986-12-23 | 1997-07-15 | Tristrata Technology, Inc. | Method of using methyllactic acid for treating wrinkles |
US5648395A (en) * | 1986-12-23 | 1997-07-15 | Tristrata Technology, Inc. | Method of using tartaric acid for treating wrinkles |
US5648391A (en) * | 1986-12-23 | 1997-07-15 | Tristrata Technology, Inc. | Method of using galacturonic acid or galacturonolactone for treating wrinkles |
US5650440A (en) * | 1986-12-23 | 1997-07-22 | Tristrata Technology, Inc. | Method of using citramalic acid for treating wrinkles |
US5650436A (en) * | 1986-12-23 | 1997-07-22 | Tristrata Technology, Inc. | Method of using galactonic acid or galactonolactone for treating wrinkles |
US5650437A (en) * | 1986-12-23 | 1997-07-22 | Tristrata Technology, Inc. | Method of using benzilic acid for treating wrinkles |
US5652267A (en) * | 1986-12-23 | 1997-07-29 | Tristrata Technology, Inc. | Method of using saccharic acid or saccharolactone for treating wrinkles |
US5654336A (en) * | 1986-12-23 | 1997-08-05 | Tristrata Technology, Inc. | Methods of using glycolic acid for reversing or retarding the effect of aging on human facial skin |
US5571841A (en) * | 1986-12-23 | 1996-11-05 | Tristrata Technology, Inc. | Method of treating wrinkles using mandelic acid |
US5389677A (en) * | 1986-12-23 | 1995-02-14 | Tristrata Inc | Method of treating wrinkles using glycalic acid |
US5385938A (en) * | 1986-12-23 | 1995-01-31 | Yu; Ruey J. | Method of using glycolic acid for treating wrinkles |
US5665776A (en) * | 1986-12-23 | 1997-09-09 | Tristrata Technology, Inc. | Additives enhancing topical actions of therapeutic agents |
US5668177A (en) * | 1986-12-23 | 1997-09-16 | Tristrata Technology, Inc. | Method of treating wrinkles using tartaric acid |
US5670543A (en) * | 1986-12-23 | 1997-09-23 | Tristrata Technology, Inc. | Method of using pantoic acid or pantolactone for treating wrinkles |
US5670542A (en) * | 1986-12-23 | 1997-09-23 | Tristrata Technology, Inc. | Method of using glucuronic acid or glucronolactone for treating wrinkles |
US5670541A (en) * | 1986-12-23 | 1997-09-23 | Tristrata Technology, Inc. | Method of treating wrinkles using gulonic acid or gulonolactone |
US5674903A (en) * | 1986-12-23 | 1997-10-07 | Tristrata Technology, Inc. | Method of using citric acid for treating wrinkles |
US5674899A (en) * | 1986-12-23 | 1997-10-07 | Tristrata Technology, Inc. | Method of using lactic acid for treating wrinkles |
US5677339A (en) * | 1986-12-23 | 1997-10-14 | Tristrata Technology, Inc. | Method of using mandelic acid for treating wrinkles |
US5677340A (en) * | 1986-12-23 | 1997-10-14 | Tristrata Technology, Inc. | Method of using gluconic acid or gluconolactone for treating wrinkles |
US5681853A (en) * | 1986-12-23 | 1997-10-28 | Tristrata Technology, Inc. | Methods for improved topical delivery of alpha hydroxyacids |
US5684044A (en) * | 1986-12-23 | 1997-11-04 | Tristrata, Incorporated | Methods for improved topical delivery of lactic acid |
US5686489A (en) * | 1986-12-23 | 1997-11-11 | Tristrata Technology, Inc. | Alpha hydroxyacid esters for skin aging |
US5691378A (en) * | 1986-12-23 | 1997-11-25 | Tristrata Technology, Inc. | Method for treating wrinkles using combinations of alpha hydroxyacids and/or alpha ketoacids |
US5690967A (en) * | 1986-12-23 | 1997-11-25 | Tristrata Technology, Inc. | Compositions for improved topical delivery of lactic acid |
US5716992A (en) * | 1986-12-23 | 1998-02-10 | Tristrata Technology, Inc. | Method of using mucic acid or mucolactone for treating wrinkles |
US5827882A (en) * | 1986-12-23 | 1998-10-27 | Tristrata Technology, Inc. | Method of using ethyl pyruvate for treating wrinkles |
US5834510A (en) * | 1986-12-23 | 1998-11-10 | Tristrata Technology, Inc. | Compositions comprising 2-hydroxycarboxylic acids and related compounds, and methods for alleviating signs of dermatological aging |
US5856357A (en) * | 1986-12-23 | 1999-01-05 | Tristrata Technology, Inc. | Method for treating wrinkles using certain alpha hydroxyacids |
US5889054A (en) * | 1986-12-23 | 1999-03-30 | Tristrata Technology, Inc. | Method of using beta hydroxy acids for treating wrinkles |
US5942250A (en) * | 1986-12-23 | 1999-08-24 | Tristrata Technology, Inc. | Compositions and methods for enhancing the topical effects of sunscreen agents |
US5962526A (en) * | 1986-12-23 | 1999-10-05 | Tristrata Technology, Inc. | Pharmaceutical compositions containing hydroxycarboxylic acids and/or ketocarboxylic acids and methods of using same |
US6384079B1 (en) | 1986-12-23 | 2002-05-07 | Tristrata Technology, Incorporated | Compositions comprising 2-hydroxycarboxylic acids and related compounds, and methods for alleviating signs of dermatological aging |
US5886041A (en) * | 1989-08-15 | 1999-03-23 | Tristrata Technology, Inc. | Amphoteric compositions and polymeric forms of alpha hydroxyacids, and their therapeutic use |
US6191167B1 (en) | 1997-12-29 | 2001-02-20 | Tristrata Technology, Inc. | Pharmaceutical compositions containing hydroxycarboxylic acid and/or ketocarboxylic acids and methods of using the same |
US6335023B1 (en) | 1999-06-30 | 2002-01-01 | Ruey J. Yu | Oligosaccharide aldonic acids and their topical use |
US6740327B2 (en) | 1999-06-30 | 2004-05-25 | Ruey J. Yu | Oligosaccharide aldonic acids and their topical use |
US20110091403A1 (en) * | 1999-06-30 | 2011-04-21 | Yu Ruey J | Oligosaccharide aldonic acids and their topical use |
US20100099632A1 (en) * | 1999-06-30 | 2010-04-22 | Yu Ruey J | Oligosaccharide Aldonic Acids and Their Topical Use |
US9456970B2 (en) | 2001-05-31 | 2016-10-04 | Upsher-Smith Laboratories, Inc. | Dermatological compositions and methods |
US8013017B2 (en) | 2001-05-31 | 2011-09-06 | Upsher-Smith Laboratories, Inc. | Dermatological compositions and methods |
US7452545B2 (en) | 2001-11-13 | 2008-11-18 | Yu Ruey J | Oligosaccharide aldonic acids and their topical use |
US20040180854A1 (en) * | 2001-11-13 | 2004-09-16 | Yu Ruey J. | Oligosaccharide aldonic acids and their topical use |
US20070134158A1 (en) * | 2002-03-14 | 2007-06-14 | Allergan, Inc. | Method for comparing multiple botulinum neurotoxins |
US20040060569A1 (en) * | 2002-03-14 | 2004-04-01 | Allergan, Inc. | Surface topography method for determining effect of a botulinum toxin upon a muscle |
US6688311B2 (en) * | 2002-03-14 | 2004-02-10 | Allergan, Inc. | Method for determining effect of a clostridial toxin upon a muscle |
US20070140969A1 (en) * | 2002-03-14 | 2007-06-21 | Allergan, Inc. | Method for comparing botulinum neurotoxins |
US7234469B2 (en) | 2002-03-14 | 2007-06-26 | Allergan, Inc. | Surface topography method for determining effect of a botulinum toxin upon a muscle |
US20070140968A1 (en) * | 2002-03-14 | 2007-06-21 | Allergan, Inc. | Method for determining botulinum potency |
US10555897B1 (en) | 2013-03-16 | 2020-02-11 | Brahm Holdings Llc | Cosmetic composition and methods of treatment |
US11382859B1 (en) | 2013-03-16 | 2022-07-12 | Brahm Holdings, Llc | Cosmetic composition and methods of treatment |
US20170157015A1 (en) * | 2014-06-18 | 2017-06-08 | Medicell Technologies, Llc | Stem cell stimulating compositions and methods |
US11491096B2 (en) * | 2014-06-18 | 2022-11-08 | Medicell Technologies, Llc | Stem cell stimulating compositions and methods |
US11865142B2 (en) | 2016-03-23 | 2024-01-09 | Mimedx Group, Inc. | Compositions and methods of treatment with amniotic fluid |
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