US3835169A - Lanolin derivatives essentially comprising esters of lanolin alcohol with lactic acid - Google Patents
Lanolin derivatives essentially comprising esters of lanolin alcohol with lactic acid Download PDFInfo
- Publication number
- US3835169A US3835169A US00156023A US15602371A US3835169A US 3835169 A US3835169 A US 3835169A US 00156023 A US00156023 A US 00156023A US 15602371 A US15602371 A US 15602371A US 3835169 A US3835169 A US 3835169A
- Authority
- US
- United States
- Prior art keywords
- lanolin
- esters
- alcohol
- acid
- lactic acid
- 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
- 239000004166 Lanolin Substances 0.000 title claims abstract description 92
- 235000019388 lanolin Nutrition 0.000 title claims abstract description 89
- 229940039717 lanolin Drugs 0.000 title claims abstract description 76
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 title claims abstract description 39
- 150000002148 esters Chemical class 0.000 title abstract description 31
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 title abstract description 25
- 235000014655 lactic acid Nutrition 0.000 title abstract description 12
- 239000004310 lactic acid Substances 0.000 title abstract description 12
- 150000001875 compounds Chemical class 0.000 claims description 9
- 239000000203 mixture Substances 0.000 abstract description 37
- 235000014113 dietary fatty acids Nutrition 0.000 abstract description 17
- 239000000194 fatty acid Substances 0.000 abstract description 17
- 229930195729 fatty acid Natural products 0.000 abstract description 17
- 238000006243 chemical reaction Methods 0.000 abstract description 14
- 239000002537 cosmetic Substances 0.000 abstract description 12
- 150000004665 fatty acids Chemical class 0.000 abstract description 11
- 239000004615 ingredient Substances 0.000 abstract description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- 229910001868 water Inorganic materials 0.000 description 25
- 239000002253 acid Substances 0.000 description 24
- 229940099367 lanolin alcohols Drugs 0.000 description 16
- 238000000034 method Methods 0.000 description 15
- 150000007513 acids Chemical class 0.000 description 13
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 12
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 11
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 11
- -1 Aliphatic alcohols Chemical class 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 239000006071 cream Substances 0.000 description 9
- 238000009472 formulation Methods 0.000 description 8
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 8
- 238000005886 esterification reaction Methods 0.000 description 7
- BILPUZXRUDPOOF-UHFFFAOYSA-N stearyl palmitate Chemical class CCCCCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCC BILPUZXRUDPOOF-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 6
- 235000012000 cholesterol Nutrition 0.000 description 6
- 230000032050 esterification Effects 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 5
- 239000002480 mineral oil Substances 0.000 description 5
- 235000010446 mineral oil Nutrition 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000004264 Petrolatum Substances 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 210000004209 hair Anatomy 0.000 description 4
- 150000003903 lactic acid esters Chemical class 0.000 description 4
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 4
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 4
- 229940066842 petrolatum Drugs 0.000 description 4
- 235000019271 petrolatum Nutrition 0.000 description 4
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 4
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 4
- 229960003415 propylparaben Drugs 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 229930182558 Sterol Natural products 0.000 description 3
- 239000004203 carnauba wax Substances 0.000 description 3
- 235000013869 carnauba wax Nutrition 0.000 description 3
- 239000007795 chemical reaction product 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
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229940049964 oleate Drugs 0.000 description 3
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 150000003432 sterols Chemical class 0.000 description 3
- 235000003702 sterols Nutrition 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 239000011787 zinc oxide Substances 0.000 description 3
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910052788 barium Inorganic materials 0.000 description 2
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- 235000013871 bee wax Nutrition 0.000 description 2
- 239000012166 beeswax Substances 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 2
- 229940070765 laurate Drugs 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 2
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 2
- 229960002216 methylparaben Drugs 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- 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
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
- RJQQOKKINHMXIM-UHFFFAOYSA-N 2-hydroxypropanoate;tris(2-hydroxyethyl)azanium Chemical compound CC(O)C(O)=O.OCCN(CCO)CCO RJQQOKKINHMXIM-UHFFFAOYSA-N 0.000 description 1
- WLAMNBDJUVNPJU-UHFFFAOYSA-N 2-methylbutyric acid Chemical compound CCC(C)C(O)=O WLAMNBDJUVNPJU-UHFFFAOYSA-N 0.000 description 1
- 239000004255 Butylated hydroxyanisole Substances 0.000 description 1
- 101100264195 Caenorhabditis elegans app-1 gene Proteins 0.000 description 1
- 241000723346 Cinnamomum camphora Species 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 239000004141 Sodium laurylsulphate Substances 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 description 1
- SEQDDYPDSLOBDC-UHFFFAOYSA-N Temazepam Chemical compound N=1C(O)C(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 SEQDDYPDSLOBDC-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 239000000061 acid fraction Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 235000019282 butylated hydroxyanisole Nutrition 0.000 description 1
- 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 1
- 229940043253 butylated hydroxyanisole Drugs 0.000 description 1
- 229960000846 camphor Drugs 0.000 description 1
- 229930008380 camphor Natural products 0.000 description 1
- 239000004204 candelilla wax Substances 0.000 description 1
- 235000013868 candelilla wax Nutrition 0.000 description 1
- 229940073532 candelilla wax Drugs 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000007766 cera flava Substances 0.000 description 1
- HBHZKFOUIUMKHV-UHFFFAOYSA-N chembl1982121 Chemical compound OC1=CC=C2C=CC=CC2=C1N=NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O HBHZKFOUIUMKHV-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000004332 deodorization Methods 0.000 description 1
- 230000001877 deodorizing effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 230000001815 facial effect Effects 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- YQEMORVAKMFKLG-UHFFFAOYSA-N glycerine monostearate Natural products CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 description 1
- SVUQHVRAGMNPLW-UHFFFAOYSA-N glycerol monostearate Natural products CCCCCCCCCCCCCCCCC(=O)OCC(O)CO SVUQHVRAGMNPLW-UHFFFAOYSA-N 0.000 description 1
- 230000003370 grooming effect Effects 0.000 description 1
- IUJAMGNYPWYUPM-UHFFFAOYSA-N hentriacontane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC IUJAMGNYPWYUPM-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229940105132 myristate Drugs 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 210000003739 neck Anatomy 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003883 ointment base Substances 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
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000473 propyl gallate Substances 0.000 description 1
- 235000010388 propyl gallate Nutrition 0.000 description 1
- 229940075579 propyl gallate Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 239000012177 spermaceti Substances 0.000 description 1
- 229940084106 spermaceti Drugs 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- TUNFSRHWOTWDNC-UHFFFAOYSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 1
- BORJONZPSTVSFP-UHFFFAOYSA-N tetradecyl 2-hydroxypropanoate Chemical compound CCCCCCCCCCCCCCOC(=O)C(C)O BORJONZPSTVSFP-UHFFFAOYSA-N 0.000 description 1
- SWGJCIMEBVHMTA-UHFFFAOYSA-K trisodium;6-oxido-4-sulfo-5-[(4-sulfonatonaphthalen-1-yl)diazenyl]naphthalene-2-sulfonate Chemical compound [Na+].[Na+].[Na+].C1=CC=C2C(N=NC3=C4C(=CC(=CC4=CC=C3O)S([O-])(=O)=O)S([O-])(=O)=O)=CC=C(S([O-])(=O)=O)C2=C1 SWGJCIMEBVHMTA-UHFFFAOYSA-K 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/003—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with alcohols
Definitions
- ABSTRACT Lanolin derivatives essentially comprising esters of lanolin alcohol with lactic acid and higher fatty acids are provided. The derivatives are prepared by direct reaction of lanolin alcohol with the higher fatty acid.
- the lanolin derivatives disclosed are especially adapted for use as essential or advantageous ingredients of various cosmetic compositions.
- lanolin commonly termed wool wax or wool fat
- cosmetic compositions as well as in various other products, including pharmaceutical preparations, textile lubricants, textile softening agents, etc.
- Lanolin is generally considered to consist of a mixture of naturally formed esters, derived from higher alcohols and higher fatty acids.
- a highly valuable constituent of lanolin is cholesterol.
- the lanolin alcohol portion of lanolin wax is believed to be of the following composition (determined by column chromatography):
- n-alkanoic acids 7 iso-alkanoic acids 23 ante-iso-alkanoic acids hydroxy-alkanoic acids 28 unidentified l2
- Lanolin alcohols and lanolin acids separated from wool wax and isolated from each other by the procedure above described are of technical grade.
- the principal object of the invention is to provide new compounds constituting derivatives of lanolin.
- lanolin which are lactic acid esters and fatty acid esters of lanolin alcohols.
- Another object of the invention is to provide a method for the preparation of such esters.
- Still another object of the invention is to provide a method for producing, in satisfactory yields, compounds constituting improved lactic acid esters and fatty acid esters of lanolin alcohols.
- a still further object of'the invention is to provide improved cosmetic and other industrial compositions utilizing lactic acid and fatty acid esters of lanolin alcohols as an active ingredient thereof, whereby to impart various desirable properties and advantages to such compositions.
- esters of lanolin alcohol herein described produced by the esterification procedure hereinafter more fully set forth.
- the lanolin alcohol esters of the present invention may be produced by the direct reaction of refined lanolin alcohol with lactic acid or with one of the enumerated fatty acids.
- the lanolin alcohol utilized is the entire wool wax alcohol fraction containing all of the sterols (including cholesterol) isolated from the wool wax.
- the lanolin alcohol used in forming the esters hereof consist of the entire alcohol fraction of wool wax, but it is further characterized by being refined from the technical lanolin alcohols normally isolated from wool wax.
- lanolin alcohols resulting from a distillation and deodorization treatment of technical lanolin alcohols.
- a preferred form of such treatment is described in the US. Pat. Nos. to Richey et al, 3,272,850 and 3,272,851.
- the aforesaid treatment consists of subjecting the technical lanolin alcohols, in the form of a slowly moving, whirling or so-called wiped film of relatively minute thickness, to contact with a heated surface while held under vacuum, and simultaneously subjecting the thus heated film to the stripping action of a counter-current flow of steam.
- the thus refined lanolin alcohol is also treated to bleach or decolorize the same, following the refining treatment.
- the fatty acids employed in esterifying the refined lanolin alcohols to produce the esters of the present invention may be selected from among the fatty acids of 10 or more, preferably 12 to 18, carbon atoms.
- lanolin alcohol esters embodying the invention may be made with lactic acid.
- the acids employed for esterifying the refined lanolin alcohols in accordance with the invention preferably include lauric, myristic, palmitic, isostearic and oleic, as well as lactic acid.
- esters are formed by direct reaction of the refined lanolin alcohol with the selected acid, without necessity of using a solvent during the reaction.
- the reaction be performed in the presence of a suitable catalyst.
- para-toluenesulfonic acid in the amount of about 0.5 gram per mol of lanolin alcohol has been found to be suitable.
- the lanolin alcohol and the selected acid are mixed, the catalyst then added, and the mixture heated. Nitrogen sparge was utilized, as was also stirring of the mixture. Temperature ranges were generally from 85C to' 170 C. Water of reaction was removed through a suitable condenser, and the reactions were continued until an acid value of 15 or less was attained. Esterification was achieved within a heating time of from approximately four to eleven hours.
- the reaction products were washed to remove excess acid.
- the compounds were dissolved in benzene and a calculated amount of a 10% solution of potassium hydroxide was added. After the formed emulsion had separated, the benzene layer was washed with saturated salt water until neutral. Where necessary, or desirable, the color of the compound was lightened by solution in isopropanol and treatment with charcoal. The compounds are thereby rendered ready for testing and use.
- esters of lanolin alcohol produced with the above-named acids together with the temperature range and heating time utilized in the preparation
- the esters embodying the invention are prepared by esterifying refined lanolin alcohols containing the cholesterol and other sterol components of wool wax, with the named acids.
- the resulting esters are in sharp contrast to the compounds referred to in the above-mentioned article by Van Dam, formed by esterification of so-called wool wax alcohols L0.
- the expression wool wax alcohol L refers to the residual wool wax alcohols remaining after the cholesterol has been removed.
- reaction product 100 grams were dissolved in benzene, as in Example I, and the solution shaken with alkali removal of excess acid, following which the benzene layer was separated from the aqueous layer and the benzene distilled in vacuo. After elimination of the benzene, the product could be crystallized readily from solution in isopropanol.
- esters embodying the invention will vary to some extent, depending primarily upon the properties of the starting materials.
- compositions are non-greasy and serves as an excellent base for cleasing creams and so-called night creams. 1t very effectively removes lipstick and eye make-up by use of tissue.
- the preparation of the lanolin lactate differed from that utilized for preparation of the other esters listed in W that the reaction of the lanolin alcohol and the lactic Tegacid, Reg. 2.00 acid was carried out under vacuum (water pump 54 g zlg 238 mm) Also, with respect to this ester, the procedure lsopropyl palmitate 4 3:00 utilized for washing the same differed from that utilized Lanolm Myrislate 5-00 for the washing of the other esters listed, in that in this W1,tcr phase instance the washing was performed with water only. Deionized water 55.40
- This vanishing cream composition is characterized by g a ggs cgg gl 21, its ability to spread easily on the skin, and to leave a Hydroxyl Value Saponification Value Water Absorption USP (Modified for 3 hours) USP, Hanus Special Procedure of Malmstrom Chemical Corporation Reference has hereinabove been made to the fact that the lanolin esters of the invention possess properties which render them especially suitable and advantageous for use in the preparation of cosmetic compositions.
- formulations for a variety of cosmetic compositions are set forth, wherein these esters constitute essential ingredients of the formulations. These formulations are as follows:
- EXAMPLE 1 W/O Emulsion Phase A W W% Beeswax, white 16 Mineral oil (70 visc.) 50 Lanolin oleate 2 Phase B Deionized water Borax I semi-matt film; also by ability to aid in retention of facial powder.
- Moisture Cream which possess long term thermal stability, and have excellent gloss, smoothness with a slightly oily-feel, and are non-tacky and cosmetically elegant.
- the lanolin lactate functions as a highly effective emulsifier when Lipsticks W/W% W/W% W/W% Candclilla wax 5.00 5.00 Carnauba wax 2.00 2.00 2.00 Ozokcrite 1.50 1.50 1.50 Spermaceti 1.50 1.50 1.50 Myristyl lactate 4.00 4.00 4.00 Mineral oil, 70 visc. 5.00 5.00 Tenox 2 butylated hydroxyanisole; 0.30 0.30 0.30 0.30 0.30 0.30 0.30 0.30 0.30 0.30 0.30 0.30 0.30 0.30 0.30 0.30 0.30 0.30 0.30 0.30 0.30 0.30 0.30 0.30 0.30 0.30 0.30 0.30 0.30 0.30 0.30 0.30 0.30 0.30 0.30 0.30 0.30 0.30 0.30 0.30 0.30 0.30 0.30 0.30 0.30 0.30 0.30 0.30 0.30 0.30 0.30 0.30 0.30 0.30 0.30 0.30 0.30 0.30 0.30 0.30 0.30 0.30
- the ester of lanolin alcohol and lactic acid has been found to possess properties which enable it to impart advantageous characteristics not only to lipstick compositions, but to other cosmetic compositions as well.
- Phase A is heated to 75C.. and phase B is heated to 75C. Phase A is added to phase B at 75C. The resultant composition is then cooled to C.
- the resultant composition is an ointment of heavy lotion-like character. It exhibits a relatively high degree of gloss and sheen and a desirable cosmetic look". lts phase properties enable it to be packaged in and used from either a jar or other container.
- the latter is added to the former.
- the zinc oxide and talc are then slowly added, and the composition is allowed to cool to room temperature. It exhibited a desirable white color and a very good appearance and a highgloss.
- the ingredients are' fnixed. maritime is heated until uniform and is poured into jars at 65-70C.
- the tests of this composition show that the lanolin lactate present therein enables the composition to yield an improved and superior hair groom, as compared to the same composition utilizing fatty alcohol (e.g.. cetyl) lactates and not lanolin lactate.
- the hair grooming product above set forth is more homogenous and without substantial tackiness. lt imparts a very good sheen to the hair. and one in which the presence of petroleum in the composition is not discernible by showing through.
- the ingredients of th oiTpliase are mixed, and this phase is heated to C.
- the Carbopol is added slowly to the water phase under good agitation. This phase is heated to 75C. and the other three ingredients of this phase are added thereto.
- the oil phase is then added to the water phase at 75C. Upon com pletion of formation of the emulsified product. it is cooled to 30C.
- the resulting cream exhibits a substantially improved capacity for serving as a barrier against water, as compared to bamer cream formulations heretofore proposed.
- a derivative of lanolin consisting essentially of an ester of a lanolin alcohol consisting of the entire wool wax alcohol fraction containing all of the sterols, including cholesterol, isolated from the wool wax, the acid fraction of said ester being derived from lactic acid.
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Abstract
Lanolin derivatives essentially comprising esters of lanolin alcohol with lactic acid and higher fatty acids are provided. The derivatives are prepared by direct reaction of lanolin alcohol with the higher fatty acid. The lanolin derivatives disclosed are especially adapted for use as essential or advantageous ingredients of various cosmetic compositions.
Description
United States Patent 1191 Kraft et al.
11] 3,835,169 Sept. 10, 1974 LANOLIN DERIVATIVES ESSENTIALLY COMPRISING ESTERS OF LANOLIN ALCOHOL WITH LACTIC ACID [76] Inventors: Elise Kraft, 2109 Broadway, New
York, N .Y. 10023; Mitchell L. Schlossman, 20 Lake Shore Dr., Rockway, NJ. 07866 22 Filed: June 23, 1971 21 App1.No.: 156,023
[52] US. Cl 260/397.2, 260/410, 260/410.6,
260/410.9, 260/484 R, 424/70, 424/365, 424/64 [51] Int. CL... Cllb 11/00, C07c 69/68, A61k 7/00 [58] Field of Search 260/410, 410.9 R, 397.2,
OTHER PUBLICATIONS Conrad et al., American Perfumer and Cosmetics, vol.
Pattison, Fatty Acids and Their Industrial Applications, Marcel Dekker, Inc, N.Y., (1968) pp. 221-224.
Van Dam et al., American Perfumer and Cosmetics 84 8/69, PP. 37-40.
Condensed Chemical Dictionary, 6th ed., Reinhold Publishing Corp., New York, 1961 p. 484.
Primary Examiner-Lewis Gotts Assistant Examiner-Diana G. Rivers [5 7] ABSTRACT Lanolin derivatives essentially comprising esters of lanolin alcohol with lactic acid and higher fatty acids are provided. The derivatives are prepared by direct reaction of lanolin alcohol with the higher fatty acid.
The lanolin derivatives disclosed are especially adapted for use as essential or advantageous ingredients of various cosmetic compositions.
2 Claims, No Drawings LANOLIN DERIVATIVES ESSENTIALLY COMPRISING ESTERS OF LANOLIN ALCOHOL WITH LACTIC ACID This invention relates to new compounds which are derivatives of lanolin. More particularly the invention relates to esters of lanolin alcohols with lactic acid and higher fatty acids.
As is well known, lanolin (frequently termed wool wax or wool fat) is extensively used in cosmetic compositions, as well as in various other products, including pharmaceutical preparations, textile lubricants, textile softening agents, etc.
Lanolin is generally considered to consist of a mixture of naturally formed esters, derived from higher alcohols and higher fatty acids. A highly valuable constituent of lanolin is cholesterol.
The alcohol and acid components of lanolin have become of increasing importance in recent years. Processes for obtaining these two components'by saponifying lanolin and then separating the lanolin alcohols from the lanolin acids are quite well known.
A recently described process for such separation is referred to in an article by Van Dam which appears at pages 37-40, Vol. 84 of American Perfumer and Cosmetics (August, 1969). As there described, the process entails first saponifying the wool wax (as by alcoholic alkali), and separating the alkaline soaps of the lanolin acids from the unsaponifiable portion containing the lanolin alcohols.
The lanolin alcohol portion of lanolin wax is believed to be of the following composition (determined by column chromatography):
Cholesterol 32.5% lsocholesterol 44.2% Aliphatic alcohols l4.7% Aliphatic diols 3.2% Hydrocarbons 0.9%
n-alkanoic acids 7 iso-alkanoic acids 23 ante-iso-alkanoic acids hydroxy-alkanoic acids 28 unidentified l2 Lanolin alcohols and lanolin acids separated from wool wax and isolated from each other by the procedure above described are of technical grade.
Previous efforts to produce fatty acid esters of wool wax alcohols by esterification of lanolin alcohol with such acids have resulted in producing commercially un satisfactory yields of the esters, and in producing esters which fail to exhibit desired properties.
The principal object of the invention is to provide new compounds constituting derivatives of lanolin.
More specifically, it is an object of the invention to provide derivatives of lanolin which are lactic acid esters and fatty acid esters of lanolin alcohols.
Another object of the invention is to provide a method for the preparation of such esters.
Still another object of the invention is to provide a method for producing, in satisfactory yields, compounds constituting improved lactic acid esters and fatty acid esters of lanolin alcohols.
A still further object of'the invention is to provide improved cosmetic and other industrial compositions utilizing lactic acid and fatty acid esters of lanolin alcohols as an active ingredient thereof, whereby to impart various desirable properties and advantages to such compositions.
The aforementioned objects of the invention may be achieved by the esters of lanolin alcohol herein described, produced by the esterification procedure hereinafter more fully set forth.
Briefly stated, the lanolin alcohol esters of the present invention may be produced by the direct reaction of refined lanolin alcohol with lactic acid or with one of the enumerated fatty acids. The lanolin alcohol utilized is the entire wool wax alcohol fraction containing all of the sterols (including cholesterol) isolated from the wool wax.
In accordance with the invention, not only does the lanolin alcohol used in forming the esters hereof consist of the entire alcohol fraction of wool wax, but it is further characterized by being refined from the technical lanolin alcohols normally isolated from wool wax.
By the term refinedas employed herein to refer to the lanolin alcohols utilized in producing the esters of the present invention, is meant lanolin alcohols resulting from a distillation and deodorization treatment of technical lanolin alcohols. A preferred form of such treatment is described in the US. Pat. Nos. to Richey et al, 3,272,850 and 3,272,851.
The aforesaid treatment, briefly stated, consists of subjecting the technical lanolin alcohols, in the form of a slowly moving, whirling or so-called wiped film of relatively minute thickness, to contact with a heated surface while held under vacuum, and simultaneously subjecting the thus heated film to the stripping action of a counter-current flow of steam.
The described action apparently results in so modifying and deodorizing the technical lanolin alcohols as to enable them to react in a more desirably effective manner in the esterification reaction with the hereinmentioned acids, and thus to yield the lanolin alcohol esters of the invention.
Preferably, the thus refined lanolin alcohol is also treated to bleach or decolorize the same, following the refining treatment.
The fatty acids employed in esterifying the refined lanolin alcohols to produce the esters of the present invention may be selected from among the fatty acids of 10 or more, preferably 12 to 18, carbon atoms.
In addition to the esters made with the aforementioned fatty acids, lanolin alcohol esters embodying the invention may be made with lactic acid.
The acids employed for esterifying the refined lanolin alcohols in accordance with the invention preferably include lauric, myristic, palmitic, isostearic and oleic, as well as lactic acid.
As above indicated, the esters are formed by direct reaction of the refined lanolin alcohol with the selected acid, without necessity of using a solvent during the reaction.
In the practice of the esterification method of the invention, it is preferred that the reaction be performed in the presence of a suitable catalyst. To that end, para-toluenesulfonic acid in the amount of about 0.5 gram per mol of lanolin alcohol has been found to be suitable.
The lanolin alcohol and the selected acid are mixed, the catalyst then added, and the mixture heated. Nitrogen sparge was utilized, as was also stirring of the mixture. Temperature ranges were generally from 85C to' 170 C. Water of reaction was removed through a suitable condenser, and the reactions were continued until an acid value of 15 or less was attained. Esterification was achieved within a heating time of from approximately four to eleven hours.
Upon completion of the esterification, the reaction products were washed to remove excess acid. For that purpose, the compounds were dissolved in benzene and a calculated amount of a 10% solution of potassium hydroxide was added. After the formed emulsion had separated, the benzene layer was washed with saturated salt water until neutral. Where necessary, or desirable, the color of the compound was lightened by solution in isopropanol and treatment with charcoal. The compounds are thereby rendered ready for testing and use.
The esters of lanolin alcohol produced with the above-named acids, together with the temperature range and heating time utilized in the preparation As hereinabove indicated, the esters embodying the invention are prepared by esterifying refined lanolin alcohols containing the cholesterol and other sterol components of wool wax, with the named acids. The resulting esters are in sharp contrast to the compounds referred to in the above-mentioned article by Van Dam, formed by esterification of so-called wool wax alcohols L0. The expression wool wax alcohol L, as indicated by Van Dam, refers to the residual wool wax alcohols remaining after the cholesterol has been removed.
Herebelow are set forth examples of a number of lanolin esters embodying the invention, together with the method for preparing the same.
EXAMPLE I LANOLIN LAURATE 200.3 grams (1m) of lauric acid, 362 grams (1m) of refined lanolin alcohol and 0.5 gram para-toluenesulfonic acid were charged into a suitable reaction vessel having four necks. Provision for stirring the mixture was made, a nitrogen sparge was attached, and a condenser for water take-off was also hooked up.
Heat was applied until the reactants were melted, whereupon agitation was initiated. Water began to appear and be driven off at about C. Heating was continued for ten hours, maintaining the reaction mixture at a temperature of from 1 15C to about C. A total of 14 cc. water was obtained. Aliquot portions of the reaction were taken until an acid value of 15 was reached. 100 grams of the reaction product were dissolved in 300 cc. of benzene. This solution was shaken with 40 cc. of a ten percent aqueous solution of potassium hydroxide, the benzene layer was separated from the aqueous layer and washed with three 100 cc. portions of water. Benzene was stripped from the washed solution in vacuo, thereby yielding the lanolin laurate. The product was then decolorized by means of isopropanol as solvent, and charcoal as the decolorizing agent.
EXAMPLE II LANOLIN PALMITATE 724 grams (2m) of refined lanolin alcohol, 512 grams (2m) of palmitic acid and 1 gram of para-toluenesulfonic acid were charged to a four-neck reaction vessel fitted with a nitrogen sparge, a water take-off condenser, and a stirrer. After melting of the components of the reaction mixture in the vessel through the application of heat, water was evolved at 140C. Heating of the mixture was continued for five and one-half hours, during which the temperature of the mixture maintained was in the range of from 135C to C. A total of approximately 17 cc. of water was obtained in the reaction, and the final acid value was 15.4. 100 grams of the reaction product were dissolved in benzene, as in Example I, and the solution shaken with alkali removal of excess acid, following which the benzene layer was separated from the aqueous layer and the benzene distilled in vacuo. After elimination of the benzene, the product could be crystallized readily from solution in isopropanol.
EXAMPLE III LANOLIN ISOSTEARATE 181 grams (%m) of lanolin alcohol, 142.2 grams of isostearic acid, 1 gram of para-toluenesulfonic acid, and 300 cc. of benzene were charged into a suitable reaction vessel, fitted with a Dean Stark trap, with a condenser and a stirrer. The reaction mixture in the vessel was refluxed and the amount of water accumulated in the Dean Stark trap was recorded. Heating of the mixture at reflux conditions was continued for approximately 21 hours, until 8.1 cc. of water was removed. 12 grams KOH in 600 cc. of water were added in a separatory funnel and the layers were separated. The benzene layer was washed with two 100 cc. portions of water, and the benzene was then stripped under vacuo.
The foregoing examples of procedure for preparing certain of the esters of lanolin alcohol embodying the invention, should make it evident that the same or similar procedure will be suitable for the preparation of others of the esters of lanolin alcohol embodying the present invention.
As will be evident to those skilled in the art, the precise physical constants of the esters embodying the invention will vary to some extent, depending primarily upon the properties of the starting materials.
properties at a relative-low concentration and without necessity for the presence of any auxiliary emulsifier. The composition is non-greasy and serves as an excellent base for cleasing creams and so-called night creams. 1t very effectively removes lipstick and eye make-up by use of tissue.
Vanishing Cream (O/W) of wool wax, with the same acids.
The preparation of the lanolin lactate differed from that utilized for preparation of the other esters listed in W that the reaction of the lanolin alcohol and the lactic Tegacid, Reg. 2.00 acid was carried out under vacuum (water pump 54 g zlg 238 mm) Also, with respect to this ester, the procedure lsopropyl palmitate 4 3:00 utilized for washing the same differed from that utilized Lanolm Myrislate 5-00 for the washing of the other esters listed, in that in this W1,tcr phase instance the washing was performed with water only. Deionized water 55.40
In Table B herebelow are set forth the physical con- "?8 stants for a number of the preferred acid esters of lano- Propylene glycol 10.00 1m alcohol embodying the invention. 0000 TABLE B Acid M.P Color- Sap. Water OH 1 Val. "C Gardner Val. Absorp. Val Val.
Lanolin Lactate 1.2 42.1 9 /240 125.5 340 118.9 29.5 Lanolln Laurate .24 47.3 4-5 98.1 184 7.0 28.3 Lanolin Myristate .61 41 992-10 102.7 96 12.0 30.7 Lanolin Palmitate .25 49.7 2-3 88.8 102 7.5 29.6 Lanolin lsostearate .40 Semi- 1213 82.9 198 9.9 27.0
liquid Lanolin Oleate .75 Liquid 11 12 83.9 120 7.6 55.3
Methods of analysis: This vanishing cream composition is characterized by g a ggs cgg gl 21, its ability to spread easily on the skin, and to leave a Hydroxyl Value Saponification Value Water Absorption USP (Modified for 3 hours) USP, Hanus Special Procedure of Malmstrom Chemical Corporation Reference has hereinabove been made to the fact that the lanolin esters of the invention possess properties which render them especially suitable and advantageous for use in the preparation of cosmetic compositions. In the Examples herebelow, formulations for a variety of cosmetic compositions are set forth, wherein these esters constitute essential ingredients of the formulations. These formulations are as follows:
EXAMPLE 1 W/O Emulsion Phase A W W% Beeswax, white 16 Mineral oil (70 visc.) 50 Lanolin oleate 2 Phase B Deionized water Borax I semi-matt film; also by ability to aid in retention of facial powder.
The following formulations are for enriched moisture creams, each made with a higher fatty acid ester of lanolin alcohol, embodying the invention:
Moisture Cream which possess long term thermal stability, and have excellent gloss, smoothness with a slightly oily-feel, and are non-tacky and cosmetically elegant.
The formulations shown in the following tabulation illustrate serveral lipstick compositions utilizing lanolin lactate or one of the higher fatty acid esters of lanolin alcohol embodying the invention:
The mixture of the above ingredients is heated until it is uniform (80C.). and is then cooled to room temperature. 1n the foregoing formulation. the lanolin lactate functions as a highly effective emulsifier when Lipsticks W/W% W/W% W/W% Candclilla wax 5.00 5.00 5.00 Carnauba wax 2.00 2.00 2.00 Ozokcrite 1.50 1.50 1.50 Spermaceti 1.50 1.50 1.50 Myristyl lactate 4.00 4.00 4.00 Mineral oil, 70 visc. 5.00 5.00 5.00 Tenox 2 butylated hydroxyanisole; 0.30 0.30 0.30
6% propyl gallate',
4% citric acid;
70% propylene glycol Yellow beeswax 8.00 8.00 8.00 Nodorlan" (lanolin purified) 10.00 10.00 10.00
according to process of U.S. Pat. No. 3,272,850) Lantrol (lanolin fraction prepared 5.00 5.00 5.00
according to the process of U.S. patent 2,758,125 and purified according to process of U.S. patent 3,272,850) Perfume 0.75 0.75 0.75 castor oil soln of TiO 31.95 31.95 31.95 C-l5004 (brilliant scarlet barium lake dye) 6.00 6.00 6.00 076001 (permanent orange, barium lake dye) 6.00 6.00 6.00 3621 (pale bromo dye) 3.00 3.00 3.00 Lanolin Myristate 10.00 Lanolin Lactate 10.00 Lanolin Oleate 10.00
The ester of lanolin alcohol and lactic acid has been found to possess properties which enable it to impart advantageous characteristics not only to lipstick compositions, but to other cosmetic compositions as well.
Illustrating such cosmetic compositions are those of the formulations shown below:
No. 1 O/W Ointment Base Qil Ehasc A WZW% Lanolin lactate 19.24 Petrolatum 16.00 Propyl Parabcn 0.10
Water Phase B Sodium lauryl sulphate 0.66 Propylene glycol 12.00 H20 $1.90 Methyl Paraben 0.10 100.00
Phase A is heated to 75C.. and phase B is heated to 75C. Phase A is added to phase B at 75C. The resultant composition is then cooled to C.
The resultant composition is an ointment of heavy lotion-like character. It exhibits a relatively high degree of gloss and sheen and a desirable cosmetic look". lts phase properties enable it to be packaged in and used from either a jar or other container.
No. 2 Absorption Base W/W% Mineral oil 31.9
Lanolin lactate 38.0
Wool wax alcohol 100 Petrolatum 16.0
Paraffin 4.0
Propyl Paraben 0.1
No. 3 Zinc Oxide Ointment W/W% Zinc oxide 40.0) C Talc 5.0) Petrolatum 33.0) A Mineral oil 10.0) Lanolin lactate 7.0) B Water 5.0)
the latter is added to the former. The zinc oxide and talc are then slowly added, and the composition is allowed to cool to room temperature. It exhibited a desirable white color and a very good appearance and a highgloss.
No. 4 Cake Mascara W/W% Carnauba wax Beeswax Glycerol Monostearate,
(non-self emulsifying) Stearic acid (3x) Sodium stearate (C-l) Propyl Paraben Lanolin lactate Triethanolamine Cab-O-Sil M-S (silicon dioxide, fine form sub-micron size) Carbon black No. Lip Ice W/W% Carnauba wax Castor oil 7 Ozokerite Candelilla wax Propyl Paraben Lanolin lactate 1 Camphor No. 6 Hair Pomade W/W% Petrolatum 50.0
Lanolin lactate 15.0
High Viscosity Mineral oil 30.0
PEG monostearate 5.0
"The ingredients are' fnixed. maritime is heated until uniform and is poured into jars at 65-70C. The tests of this composition show that the lanolin lactate present therein enables the composition to yield an improved and superior hair groom, as compared to the same composition utilizing fatty alcohol (e.g.. cetyl) lactates and not lanolin lactate. The hair grooming product above set forth is more homogenous and without substantial tackiness. lt imparts a very good sheen to the hair. and one in which the presence of petroleum in the composition is not discernible by showing through.
No. 7 Barrier Cream Oil phase Stearic acid (3x) 3.5 Span 60 2.0 Tween 60 1.5 Lanolin lactate 10.0 Propyl Paraben 0.10
Water phase Carbopol 934 0.25 Water q.s. Triethanolamine 0.25 Propylene glycol 10.0 Methyl Paraben 0.10
The ingredients of th oiTpliase are mixed, and this phase is heated to C. The Carbopol is added slowly to the water phase under good agitation. This phase is heated to 75C. and the other three ingredients of this phase are added thereto. The oil phase is then added to the water phase at 75C. Upon com pletion of formation of the emulsified product. it is cooled to 30C. The resulting cream exhibits a substantially improved capacity for serving as a barrier against water, as compared to bamer cream formulations heretofore proposed.
What is claimed is:
l. A derivative of lanolin consisting essentially of an ester of a lanolin alcohol consisting of the entire wool wax alcohol fraction containing all of the sterols, including cholesterol, isolated from the wool wax, the acid fraction of said ester being derived from lactic acid.
2. The compound of claim 1, wherein said alcohol is refined lanolin alcohol.
Claims (1)
- 2. The compound of claim 1, wherein said alcohol is refined lanolin alcohol.
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US00156023A US3835169A (en) | 1971-06-23 | 1971-06-23 | Lanolin derivatives essentially comprising esters of lanolin alcohol with lactic acid |
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US00156023A US3835169A (en) | 1971-06-23 | 1971-06-23 | Lanolin derivatives essentially comprising esters of lanolin alcohol with lactic acid |
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Cited By (13)
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---|---|---|---|---|
US3953591A (en) * | 1974-04-29 | 1976-04-27 | The Procter & Gamble Company | Fatty acid, polysiloxane and water-soluble polymer containing skin conditioning emulsion |
US3957971A (en) * | 1974-07-29 | 1976-05-18 | Lever Brothers Company | Moisturizing units and moisturizing compositions containing the same |
US4005210A (en) * | 1975-07-03 | 1977-01-25 | Estee Lauder, Inc. | Protein containing emollient composition for a skin moisturizer |
US4035514A (en) * | 1976-02-17 | 1977-07-12 | Ici United States Inc. | Water washable petrolatum compositions |
US4066789A (en) * | 1976-03-12 | 1978-01-03 | Emery Industries, Inc. | Blends of lanolin wax and esters of aliphatic polyols and fatty acids |
US4146649A (en) * | 1976-10-14 | 1979-03-27 | Faberge, Incorporated | Skin moisturizing composition containing a polyethoxy fatty alcohol and a polyethoxy glycoside |
US4382919A (en) * | 1980-09-15 | 1983-05-10 | Bristol-Myers Company | Composition for treatment and prevention of malodorous generating skin conditions |
US4416868A (en) * | 1974-08-12 | 1983-11-22 | Societe Anonyme Dite: L'oreal | Cosmetic excipient |
FR2647805A1 (en) * | 1989-06-06 | 1990-12-07 | Bugat Maurice | Process for manufacture of fatty acid esters, corresponding isolated products and compositions for human or veterinary use containing them |
US5399730A (en) * | 1991-08-01 | 1995-03-21 | Development Products, Inc. | Method of obtaining an purified wool fat and use as an additive to lubricants |
US5783725A (en) * | 1996-02-27 | 1998-07-21 | Haarmann & Reimer Gmbh | Stabilized lactic acid menthyl ester |
EP0837049B1 (en) * | 1996-10-17 | 2002-07-31 | Rohm And Haas Company | A process for preparing monomers |
US6544349B1 (en) | 2000-11-16 | 2003-04-08 | The Fanning Corporation | Method for in situ cleaning of machine components |
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Cited By (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
USRE29814E (en) * | 1974-04-29 | 1978-10-24 | The Procter & Gamble Company | Lanolin fatty acids, polysiloxane and water-soluble polymer containing skin conditioning emulsion |
US3953591A (en) * | 1974-04-29 | 1976-04-27 | The Procter & Gamble Company | Fatty acid, polysiloxane and water-soluble polymer containing skin conditioning emulsion |
US3957971A (en) * | 1974-07-29 | 1976-05-18 | Lever Brothers Company | Moisturizing units and moisturizing compositions containing the same |
US4416868A (en) * | 1974-08-12 | 1983-11-22 | Societe Anonyme Dite: L'oreal | Cosmetic excipient |
US4005210A (en) * | 1975-07-03 | 1977-01-25 | Estee Lauder, Inc. | Protein containing emollient composition for a skin moisturizer |
US4035514A (en) * | 1976-02-17 | 1977-07-12 | Ici United States Inc. | Water washable petrolatum compositions |
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US4146649A (en) * | 1976-10-14 | 1979-03-27 | Faberge, Incorporated | Skin moisturizing composition containing a polyethoxy fatty alcohol and a polyethoxy glycoside |
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FR2647805A1 (en) * | 1989-06-06 | 1990-12-07 | Bugat Maurice | Process for manufacture of fatty acid esters, corresponding isolated products and compositions for human or veterinary use containing them |
EP0474946A1 (en) * | 1989-06-06 | 1992-03-18 | Sarpap | Process for producing fatty acid esters, corresponding isolated products and compositions for human or veterinary use containing same |
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AS | Assignment |
Owner name: HENKEL CORPORATION, A DE CORP., PENNSYLVANIA Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNOR:QUANTUM CHEMICAL CORPORATION;REEL/FRAME:005270/0484 Effective date: 19891013 |