DE753417C - Process for the production of water-in-oil emulsions, especially for cosmetic and pharmaceutical purposes - Google Patents
Process for the production of water-in-oil emulsions, especially for cosmetic and pharmaceutical purposesInfo
- Publication number
- DE753417C DE753417C DED84860D DED0084860D DE753417C DE 753417 C DE753417 C DE 753417C DE D84860 D DED84860 D DE D84860D DE D0084860 D DED0084860 D DE D0084860D DE 753417 C DE753417 C DE 753417C
- Authority
- DE
- Germany
- Prior art keywords
- acid
- water
- weight
- parts
- oil emulsions
- 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
Links
- 239000000839 emulsion Substances 0.000 title claims description 12
- 239000002537 cosmetic Substances 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 239000002253 acid Substances 0.000 claims description 23
- 150000007513 acids Chemical class 0.000 claims description 13
- 239000003921 oil Substances 0.000 claims description 11
- 239000003995 emulsifying agent Substances 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 239000007859 condensation product Substances 0.000 claims description 4
- 241001465754 Metazoa Species 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 235000013311 vegetables Nutrition 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 11
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 8
- -1 vaseline Substances 0.000 description 7
- 239000004310 lactic acid Substances 0.000 description 6
- 235000014655 lactic acid Nutrition 0.000 description 6
- 239000001993 wax Substances 0.000 description 6
- 238000009833 condensation Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 230000005494 condensation Effects 0.000 description 4
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
- 229940099259 vaseline Drugs 0.000 description 4
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 3
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 3
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 3
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 3
- 239000005642 Oleic acid Substances 0.000 description 3
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 239000006071 cream Substances 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 3
- 229940055577 oleyl alcohol Drugs 0.000 description 3
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 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 2
- ALRHLSYJTWAHJZ-UHFFFAOYSA-N 3-hydroxypropionic acid Chemical compound OCCC(O)=O ALRHLSYJTWAHJZ-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000010775 animal oil Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- ROBFUDYVXSDBQM-UHFFFAOYSA-N hydroxymalonic acid Chemical compound OC(=O)C(O)C(O)=O ROBFUDYVXSDBQM-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 2
- 239000011347 resin Chemical class 0.000 description 2
- 229920005989 resin Chemical class 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- JXNPEDYJTDQORS-HZJYTTRNSA-N (9Z,12Z)-octadecadien-1-ol Chemical compound CCCCC\C=C/C\C=C/CCCCCCCCO JXNPEDYJTDQORS-HZJYTTRNSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 1
- 241000283153 Cetacea Species 0.000 description 1
- QXKAIJAYHKCRRA-JJYYJPOSSA-N D-arabinonic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C(O)=O QXKAIJAYHKCRRA-JJYYJPOSSA-N 0.000 description 1
- JPIJQSOTBSSVTP-PWNYCUMCSA-N D-erythronic acid Chemical compound OC[C@@H](O)[C@@H](O)C(O)=O JPIJQSOTBSSVTP-PWNYCUMCSA-N 0.000 description 1
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
- RGHNJXZEOKUKBD-MBMOQRBOSA-N D-mannonic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)C(O)=O RGHNJXZEOKUKBD-MBMOQRBOSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- KCZPXDUCCAGHKE-CLFAGFIQSA-N bis[(z)-octadec-9-enyl] 2,3-dihydroxybutanedioate Chemical compound CCCCCCCC\C=C/CCCCCCCCOC(=O)C(O)C(O)C(=O)OCCCCCCCC\C=C/CCCCCCCC KCZPXDUCCAGHKE-CLFAGFIQSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000004203 carnauba wax Substances 0.000 description 1
- 235000013869 carnauba wax Nutrition 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001841 cholesterols Chemical class 0.000 description 1
- 239000003026 cod liver oil Substances 0.000 description 1
- 235000012716 cod liver oil Nutrition 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- VLHZUYUOEGBBJB-UHFFFAOYSA-N hydroxy stearic acid Natural products OCCCCCCCCCCCCCCCCCC(O)=O VLHZUYUOEGBBJB-UHFFFAOYSA-N 0.000 description 1
- 239000000832 lactitol Substances 0.000 description 1
- VQHSOMBJVWLPSR-JVCRWLNRSA-N lactitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O VQHSOMBJVWLPSR-JVCRWLNRSA-N 0.000 description 1
- 229960003451 lactitol Drugs 0.000 description 1
- 235000010448 lactitol Nutrition 0.000 description 1
- JXNPEDYJTDQORS-UHFFFAOYSA-N linoleyl alcohol Natural products CCCCCC=CCC=CCCCCCCCCO JXNPEDYJTDQORS-UHFFFAOYSA-N 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 239000012170 montan wax Substances 0.000 description 1
- 125000005608 naphthenic acid group Chemical class 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- NELZVYZKKXHHAB-IUPFWZBJSA-N tris[(z)-octadec-9-enyl] 2-hydroxypropane-1,2,3-tricarboxylate Chemical compound CCCCCCCC\C=C/CCCCCCCCOC(=O)CC(O)(C(=O)OCCCCCCCC\C=C/CCCCCCCC)CC(=O)OCCCCCCCC\C=C/CCCCCCCC NELZVYZKKXHHAB-IUPFWZBJSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/34—Higher-molecular-weight carboxylic acid esters
-
- 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
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/37—Esters of carboxylic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/04—Dispersions; Emulsions
- A61K8/06—Emulsions
- A61K8/064—Water-in-oil emulsions, e.g. Water-in-silicone emulsions
-
- 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
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/37—Esters of carboxylic acids
- A61K8/375—Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Emergency Medicine (AREA)
- Dispersion Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Dermatology (AREA)
- Cosmetics (AREA)
Description
Verfahren zur Herstellung von Wasser-in-Ol-Emulsionen, besonders für kosmetische und pharmazeutische Zwecke Es wurde gefunden, daß die Kondensationsprodukte aus organischen Hydroxylverbindungen, die im Molekül lipophile Reste enthalten, und Oxycarbonsäuren wertvolle Emulgatoren darstellen, die insbesondere zur Herstellung für Wasser-in-ÖI-Emulsionen mitVorteilverwendbar sind. Die genannten Stoffe vermitteln den zu emulgierenden Substanzen, denen sie zugegeben werden, ein hervorragendes Wasserbindungsvermögen und geben Emulsionen von hoher Stabilität.Process for the preparation of water-in-oil emulsions, especially for cosmetic and pharmaceutical purposes It has been found that the condensation products from organic hydroxyl compounds that contain lipophilic residues in the molecule, and oxycarboxylic acids are valuable emulsifiers that are used in particular for production are usable with advantage for water-in-oil emulsions. Mediate the substances mentioned the substances to be emulsified to which they are added, an excellent one Water-binding capacity and give emulsions of high stability.
Für die Herstellung der Emulsionen kann man als emulgierbare Ausgangsstoffe außer den bekannten Mineralölen, -fetten und -wachsen, wie Vaseline, Paraffinöl, Ceresin usw., auch andere emulgierbare Stoffe verwenden, wie tierische und pflanzliche Öle und Fette, flüssige oder feste Wachse, synthetische Fettsäureester, Fettalkohole, Wachsalkohole u. dgl. For the production of the emulsions, emulsifiable starting materials can be used apart from the well-known mineral oils, fats and waxes, such as vaseline, paraffin oil, Ceresin, etc., also use other emulsifiable substances, such as animal and vegetable Oils and fats, liquid or solid waxes, synthetic fatty acid esters, fatty alcohols, Wax alcohols and the like
Die verwendeten Kondensationsprodukte sind an sich bekannt, sie werden aus den Ausgangsstoffen nach üblichen Veresterungsverfahren hergestellt, in der Regel bei erhöhter Temperatur unter Wasserabspaltung, wobei man die Kondensation erforderlichenfalls durch Zugabe wasserbindender Mittel oder durch geeignete Katalysatoren fördern kann. In manchen Fällen ist es zweckmäßig, an Stelle der Säuren deren Ester mit beliebigen niedermolekularen Alkoholen zu verwenden und diese auf dem Wege der Umesterung mit den organischen Hydroxylverbindungen umzusetzen. Man kann an Stelle der Säuren auch deren Alkalisalze und an Stelle der Hydroxylverbindungen entsprechende Halogenide einsetzen. Bei der Kondensation können auch gewisse Nebenreaktionen auftreten, wie z. B. Wasserabspaltung aus den Oxycarbonsäuren oder Ätherbildung. Die dabei entstehenden Nebenprodukte treten nur in untergeordneten Mengen auf und stören im allgemeinen bei der Verwendung nicht; infolgedessen kann man die Kondensationsprodukte gegebenenfalls auch ohne besondere Aufarbeitung unmittelbar verwenden. The condensation products used are known per se, they will produced from the starting materials by conventional esterification processes, in which Usually at elevated temperature with elimination of water, whereby the condensation if necessary, by adding water-binding agents or using suitable catalysts can promote. In some cases it is useful to replace the acids whose To use esters with any low molecular weight alcohols and these on the To implement ways of transesterification with the organic hydroxyl compounds. One can in place of the acids also their alkali salts and in place of the hydroxyl compounds use appropriate halides. Certain side reactions can also occur during condensation occur, such as B. elimination of water from the oxycarboxylic acids or ether formation. The resulting by-products occur only in minor amounts and generally do not interfere with use; as a result, one can use the condensation products if necessary, use immediately without any special work-up.
Die beanspruchten Emulgatoren sind ihrer Natur nach im wesentlichen Ester von Oxysäuren, deren Alkoholkomponente wenigstens einen lipophilen Rest im Molekül enthält. Unter einem lipophilen Rest versteht man einen aliphatischen oder cycloaliphatischen Kohlenwasserstoffrest von wenigstens 6 Kohlenstoffatomen oder einen cycloaliphatischen oder aromatischen Kohlenwasserstoffrest, der eine unverzweigt aliphatische Seitenkette von wenigstens 3 Kohlenstoffatomen enthält. Als Oxygruppen enthaltende Verbindungen dieser Art, die als Kondensationskomponenten für die Oxysäuren in Betracht kommen, sind insbesondere höhermolekulare gesättigte und ungesättigte aliphatische Alkohole zu nennen, wie beispielsweise Dodecylalkohol, Hexadecylalkohol, Octadecylalkohol, Oleylalkohol, Linoleylalkohol, Gemische höhermolekularer ungesättigter Alkohole, wie sie aus den flüssigen Wachsen der Seetieröle erhältlich sind, ferner andere höhermolekulare Wachsalkohole, wie Bienenwachs alkohole, Carnaubawachsalkohole und Montanwachsalkohole, sowie auch die aus Naphthensäuren und Harzsäuren durch katalytische Reduktion gewonnenen Naphthen- und Harzalkohole. In gleicher Weise kann man auch entsprechende, auf synthetischem Wege gewonnene Alkohole verwenden, beispielsweise höherinolekulare Paraffinalkohole, höhermolekulare perhydrierte Alkylphenole und -naphthole, höhermolekulare Alkohole, wie sie beispielsweise aus Laurylalkohol durch Selbstkondensation in Gegenwart alkalischer Mittel erhalten werden, u. dgl. Die Kohlenwasserstoffreste dieser Alkohole können auch Substituenten enthalten oder durch Heteroatome bzw. Heteroatomgruppen unterbrochen sein. Hierfür kommen in erster Linie sauerstoffhaltige Gruppen, wie Hydroxylgruppen, Äthergruppen und vor allem Estergruppen, in Betracht. Als Beispiele für derartige Alkohole sind zu nennen die Äthylenglykolmonoester der höhermolekularen Fettsäuren, wie Laurinsäure und Ölsäure, der Diölsäureester des I, 1, I, I-Trimethyloläthans oder der Tetraölsäureester des Dipentaerythrits sowie entsprechende Alkyläther mit höhermolekularen aliphatischen, vorzugsweise ungesättigten Alkylresten. The emulsifiers claimed are essentially essential in nature Esters of oxy acids, the alcohol component of which has at least one lipophilic radical in the Contains molecule. A lipophilic radical is understood to be an aliphatic or cycloaliphatic hydrocarbon radical of at least 6 carbon atoms or a cycloaliphatic or aromatic hydrocarbon radical that is unbranched contains aliphatic side chain of at least 3 carbon atoms. As oxy groups containing compounds of this type, which are used as condensation components for the oxyacids come into consideration are, in particular, higher molecular weight saturated and unsaturated aliphatic alcohols, such as dodecyl alcohol, hexadecyl alcohol, Octadecyl alcohol, oleyl alcohol, linoleyl alcohol, mixtures of higher molecular weight unsaturated Alcohols, such as are obtainable from the liquid waxes of marine animal oils, also other higher molecular wax alcohols, such as beeswax alcohols, carnauba wax alcohols and montan wax alcohols, as well as those made from naphthenic acids and resin acids catalytic reduction of naphthenic and resin alcohols. In the same way you can also use corresponding synthetic alcohols, for example, higher molecular weight paraffin alcohols, higher molecular weight perhydrogenated alkylphenols and naphthols, higher molecular weight alcohols, such as those from lauryl alcohol obtained by self-condensation in the presence of alkaline agents, and the like. The hydrocarbon radicals of these alcohols can also contain or contain substituents be interrupted by heteroatoms or heteroatom groups. For this come first Line oxygen-containing groups, such as hydroxyl groups, ether groups and above all Ester groups, into consideration. Examples of such alcohols are the Ethylene glycol monoesters of higher molecular weight fatty acids, such as lauric acid and oleic acid, the dioleic acid ester of I, 1, I, I-trimethylolethane or the tetraoleic acid ester of Dipentaerythritol and corresponding alkyl ethers with higher molecular weight aliphatic, preferably unsaturated alkyl radicals.
Als Oxycarbonsäuren, die als Kondensationskomponente in Betracht kommen, sind zu nennen: Glykolsäure, Milchsäure, Hydracrylsäure,Oxybuttersäuren, Oxyvaleriansäuren, Oxycapronsäuren,Oxylaurinsäuren, Oxystearinsäure, Ricinolsäure, a-Oxy-diäthylessigsäure, a-Oxytert.-butylessigsäure, ß - Diäthylidenmilchsäure, Oxäthoxyessigsäure, ferner Salicylsäure, p-Oxybenzoesäure, Oxynaphthoesäuren, Erythronsäure, Arabonsäure u. dgl. Als mehrbasische Säuren sind zu nennen: Tartronsäure, Apfelsäure, ß-Oxyisobernsteinsäure, Weinsäure, a-Oxyglutarsäure, Trioxyglutarsäure, Mannonsäure, Gluconsäure, Zitronensäure, Oxyzitronensäure, ferner Oxyisophthalsäure u. a. m. Sofern diese Oxycarbonsäuren mehrere Hydroxylgruppen enthalten, kann ein Teil dieser Hydro xylgruppen auch durch Verätherung oder Veresterung verschlossen sein. As oxycarboxylic acids that can be used as condensation components are to be mentioned: glycolic acid, lactic acid, hydracrylic acid, oxybutyric acids, Oxyvaleric acids, oxycaproic acids, oxylauric acids, oxystearic acid, ricinoleic acid, a-oxy-diethyl acetic acid, a-oxytert.-butyl acetic acid, ß - diethylidene lactic acid, Oxethoxyacetic acid, also salicylic acid, p-oxybenzoic acid, oxynaphthoic acids, erythronic acid, Arabonic acid and the like. The following polybasic acids are to be mentioned: tartronic acid, malic acid, ß-oxyisosuccinic acid, tartaric acid, a-oxyglutaric acid, trioxyglutaric acid, mannonic acid, Gluconic acid, citric acid, oxycitric acid, also oxyisophthalic acid and others. m. If these oxycarboxylic acids contain several hydroxyl groups, some of them can Hydro xyl groups can also be closed by etherification or esterification.
Ester, die erfindungsgemäß verwendet werden können, sind beispielsweise Glycolsäureoleyl ester, Milchsäureoleylester, Oxäthoxyessigsäureoleylester, Zitronensäuretrioleylester, Zitronensäure-dioleyl-octadecylester, Weinsäuredioleylester, der Ester aus I Mol I, I, I-Trimethylol propan, 2 Mol Ölsäure und I Mol Milchsäure, der Ester aus I Mol Dipentaerythrit, 4 Mol Ölsäure und 2 Mol Milchsäure u. dgl. Esters that can be used in the present invention are, for example Glycolic acid oleyl ester, lactic acid oleyl ester, oxethoxyacetic acid oleyl ester, citric acid trioleyl ester, Citric acid dioleyl octadecyl ester, tartaric acid dioleyl ester, the ester of I mol I, I, I-trimethylol propane, 2 moles of oleic acid and 1 mole of lactic acid, the ester from I. Moles of dipentaerythritol, 4 moles of oleic acid and 2 moles of lactic acid and the like.
Die Herstellung der Emulsionen erfolgt in üblicher Weise, indem man die Emulgatoren den zu emulgierenden Komponenten z. B. einverleibt und das Wasser einarbeitet, wobei man Wasser-in-Öl-Emulsionen erhält. Man kann dabei auch andere bekannte Emulgatoren mitverwenden, wie z. B. Wollfettalkohole und andere Cholesterinderivate oder Wasser-in-Öl-Emulga toren synthetischer Herkunft. The emulsions are prepared in a customary manner by the emulsifiers the components to be emulsified e.g. B. incorporated and the water incorporated, giving water-in-oil emulsions. You can do other things too use known emulsifiers, such as. B. wool fatty alcohols and other cholesterol derivatives or water-in-oil emulsifiers of synthetic origin.
Die nach diesem Verfahren erhältlichen Emulsionen haben ein großes Anwendungsgebiet in der Kosmetik, Pharmazie und Technik in Gestalt von Salben, Kremen u. dgl. Während die bisher bekannten Emulgatoren für Wasser-in-Öl-Emulsionen nur für Vaseline u. a. mineralische Stoffe zu verwenden waren, sind die erfindungsgemäßen Emulgatoren imstande, sämtliche eingangs genannten Fettstoffe jeder Art zu emulgieren. Man gelangt also mit Hilfe der erfindungsgemäßen Emulgatoren zu Wasser-in-ÖI-Emulsionen, die leicht resorbierbare hautpflegende Substanzen enthalten, die für Pharmazie und Kosmetik von großer Bedeutung sind. The emulsions obtainable by this process have a large size Application in cosmetics, pharmacy and technology in the form of ointments, creams and the like While the previously known emulsifiers for water-in-oil emulsions only for Vaseline and others Mineral substances were to be used, are those according to the invention Emulsifiers capable of emulsifying all types of fatty substances mentioned at the outset. With the aid of the emulsifiers according to the invention, water-in-oil emulsions are thus obtained, which contain easily absorbable skin care substances that are used in pharmacy and Cosmetics are of great importance.
Beispiel I I7 Gewichtsteile Oleylalkohol und 4,2 Gewichtsteile feinpulverisierte Zitronensäure werden unter Durchleiten von Wasserstoff und unter Rühren vorsichtig bis auf 235° erhitzt, bis etwa I Gewichtsteil Wasser abdestilliert ist. Example I 17 parts by weight of oleyl alcohol and 4.2 parts by weight of finely powdered Citric acid are carefully bubbled through with hydrogen and while stirring heated to 235 ° until about 1 part by weight of water has distilled off.
4 Gewichtsteile des so erhaltenen goldgelben Öls werden in 31 Gewichtsteilen Vaseline in der Wärme gelöst, worauf man nach und nach 65 Gewichtsteile Wasser von gleicher Temperatur unter Rühren zugibt. Die Wasserbindung setzt rasch ein. Der bis zum völligen Erkalten gerührte Krem ist ein hervorragendes Hautpflegemittel.4 parts by weight of the golden yellow oil thus obtained are in 31 parts by weight Vaseline dissolved in the heat, whereupon you gradually remove 65 parts by weight of water at the same temperature while stirring. The water binding sets in quickly. Of the Cream stirred until completely cold is an excellent skin care product.
Beispiel 2 Ein Gemisch von II Gewichtsteilen Oleylalkohol, 5,6 Gewichtsteilen Octadecylalkohol und 4,2 Gewichtsteilen Zitronensäure wird in der im-Beispiel I beschriebenen Weise erhitzt, wobei ein in der Kälte wachsartig erstarrender Mischester erhalten wird. 4,5 Gewichtsteile dieses Wachses löst man unter Erwärmen in einem Gemisch aus 6 Gewichtsteilen Ceresin und 25 Gewichtsteilen Vaseline und fügt unter Rühren, wie oben beschrieben, 78 Gewichtsteile Wasser hinzu. Man erhält eine stabile Wasserin-Öl-Emulsion von guter Streichfähigkeit. Example 2 A mixture of II parts by weight of oleyl alcohol, 5.6 parts by weight Octadecyl alcohol and 4.2 parts by weight of citric acid is used in the example I Heated manner described, with a waxy solidified mixed ester in the cold is obtained. 4.5 parts by weight of this wax are dissolved in a with heating Mixture of 6 parts by weight of ceresin and 25 parts by weight of Vaseline and adds underneath Stir as described above, add 78 parts by weight of water. You get a stable one Water-in-oil emulsion with good spreadability.
Beispiel 3 Ein Gemisch von I5,8 Gewichtsteilen Spermölfettsäure und 3,8 Gewichtsteilen Dipentaerythrit erhitzt man wie oben so lange bis auf 3in", bis kein Wasser mehr abdestilliert. Nach dem Abkühlen bis auf etwa I50° gibt man 2,7 Gewichtsteile Milchsäure oder 2,I6 Gewichtsteile Lactit hinzu und steigert die Temperatur erneut bis auf 270°, bis kein Wasser mehr gebildet wird. 3,7 Gewichtsteile des auf diese Weise erhaltenen gelben Öls löst man auf dem Wasserbad in einem Gemisch von I6 Gewichtsteilen Lebertran und 15 Gewichtsteilen Walrat und emulgiert in bekannter Weise mit 60 Gewichtsteilen Wasser. Die erhaltene Emulsion ist ein weißer Krem von guter Streichfähigkeit, der als Brandsalbe verwendet werden kann. Example 3 A mixture of 15.8 parts by weight of sperm oil fatty acid and 3.8 parts by weight of dipentaerythritol are heated as long as above up to 3 inches no more water distilled off. After cooling to about 150 °, 2.7 is added Parts by weight of lactic acid or 2.16 parts by weight of lactitol are added and the temperature is increased again up to 270 °, until no more water is formed. 3.7 parts by weight of the The yellow oil obtained in this way is dissolved in a mixture of on a water bath 16 parts by weight of cod liver oil and 15 parts by weight of whale rat and emulsified in a known manner Way with 60 parts by weight of water. The emulsion obtained is a white cream of good spreadability, which can be used as a burn ointment.
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Application Number | Priority Date | Filing Date | Title |
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DED84860D DE753417C (en) | 1941-04-13 | 1941-04-13 | Process for the production of water-in-oil emulsions, especially for cosmetic and pharmaceutical purposes |
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DED84860D DE753417C (en) | 1941-04-13 | 1941-04-13 | Process for the production of water-in-oil emulsions, especially for cosmetic and pharmaceutical purposes |
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1941
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