DE1215730B - Process for preparing water-in-oil emulsions - Google Patents
Process for preparing water-in-oil emulsionsInfo
- Publication number
- DE1215730B DE1215730B DEC29920A DEC0029920A DE1215730B DE 1215730 B DE1215730 B DE 1215730B DE C29920 A DEC29920 A DE C29920A DE C0029920 A DEC0029920 A DE C0029920A DE 1215730 B DE1215730 B DE 1215730B
- Authority
- DE
- Germany
- Prior art keywords
- urea
- oil emulsions
- preparing water
- monooleat
- water
- 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.)
- Pending
Links
- 239000000839 emulsion Substances 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title description 7
- 239000002253 acid Substances 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims description 2
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims description 2
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims description 2
- 239000003995 emulsifying agent Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- CUNWUEBNSZSNRX-RKGWDQTMSA-N (2r,3r,4r,5s)-hexane-1,2,3,4,5,6-hexol;(z)-octadec-9-enoic acid Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CCCCCCCC\C=C/CCCCCCCC(O)=O.CCCCCCCC\C=C/CCCCCCCC(O)=O.CCCCCCCC\C=C/CCCCCCCC(O)=O CUNWUEBNSZSNRX-RKGWDQTMSA-N 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- -1 pentaerythritol fatty acid esters Chemical class 0.000 description 2
- 229960005078 sorbitan sesquioleate Drugs 0.000 description 2
- 150000003672 ureas Chemical class 0.000 description 2
- 210000002268 wool Anatomy 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 150000001913 cyanates Chemical class 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 229940099259 vaseline Drugs 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
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
- A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
- A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/20—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing sulfur, e.g. dimethyl sulfoxide [DMSO], docusate, sodium lauryl sulfate or aminosulfonic 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
-
- 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
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/42—Amides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
-
- 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)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Dispersion Chemistry (AREA)
- Organic Chemistry (AREA)
- Materials Engineering (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Birds (AREA)
- Agronomy & Crop Science (AREA)
- Environmental Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Dentistry (AREA)
- Toxicology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Dermatology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
Description
Verfahren zum Herstellen von Wasser-in-ol-Emulsionen Zum Emulgieren von Wasser-in-Öl kann man bekanntlich im pharmazeutischen und kosmetischen Bereich Wollwachsalkohole bzw. deren Derivate sowie Sorbitan- oder Pentaerithrit-Fettsäureester verwenden.Process for preparing water-in-ol emulsions For emulsification It is well known that water-in-oil can be used in the pharmaceutical and cosmetic fields Wool wax alcohols or their derivatives and sorbitan or pentaerythritol fatty acid esters use.
Es wurde nun gefunden, daß man gegenüber der Verwendung der bekannten Emulgatoren mehr Wasser emulgieren kann, wenn man Monofettsäureester von ungesättigten Fettsäuren mit symmetrischen oder asymmetrischen disubstituierten Oxyalkylharnstoffen oder Oxyalkylthioharnstoffen der Formel bzw. in denen X und Y gleich oder verschieden sind und die Reste (CHn - (CH2)2 -0- (CH2)n - bedeuten, wobei n größer als 1 und m gleich oder größer als 1 und R ein Alkylrest einer höheren, mindestens 10 C-Atome enthaltenden, geradkettigen oder verzweigten, vorzugsweise ungesättigten Carbonsäure ist, als Emulgatoren verwendet. Diese Stoffe besitzen ein großes Wasserbindevermögen und ermöglichen die Herstellung stabiler Wasser-in-Öl-Emulsionen. Die damit hergestellten Emulsionen bedürfen keiner mechanischen Nachbehandlung, z. B. durch abschließendes Homogenisieren auf einem Walzenstuhl, wie sie bei Verwendung bekannter Emulgatoren in der Praxis allgemein üblich ist.It has now been found that, compared with the use of the known emulsifiers, more water can be emulsified if monofatty acid esters of unsaturated fatty acids with symmetrical or asymmetrical disubstituted oxyalkylureas or oxyalkylthioureas of the formula or in which X and Y are identical or different and the radicals (CHn - (CH2) 2 -0- (CH2) n - where n is greater than 1 and m is equal to or greater than 1 and R is an alkyl radical of a higher, straight-chain or branched, preferably unsaturated, carboxylic acid containing at least 10 carbon atoms, used as emulsifiers. These substances have a high water-binding capacity and enable the production of stable water-in-oil emulsions. The emulsions produced therewith do not require any mechanical aftertreatment, e.g. B. by final homogenization on a roller mill, as is common practice when using known emulsifiers.
Die erfindungsgemäß verwendeden Verbindungen lassen sich nach bekannten, hier nicht beanspruchten Verfahren herstellen, beispielsweise durch thermische oder katalytische Veresterung der entsprechenden Harnstoffderivate, durch Umesterung aus Fettsäureestern oder durch Veresterung über die entsprechenden Säurechloride der Fettsäure (vgl. zum Beispiel deut- sche Auslegeschrift 1 122 938 und USA.-Patentschrift 2 738 333). Eine andere Möglichkeit speziell für den Fall der Herstellung von asymmetrischen Harnstoffderivaten besteht in der Herstellung der Aminesterhydrochloride und anschließender Überführung der Aminogruppe mit Cyanaten in die Harnstoffgruppierung. The compounds used according to the invention can be according to known, Manufacture not claimed here processes, for example by thermal or catalytic esterification of the corresponding urea derivatives by transesterification from fatty acid esters or by esterification via the corresponding acid chlorides of fatty acids (cf., for example, German Sche Auslegeschrift 1 122 938 and U.S. Patent 2,738,333). Another option especially for the case of asymmetrical production Urea derivatives consists in the production of the amine ester hydrochloride and subsequent Conversion of the amino group with cyanates into the urea group.
Die erfindungsgemäß zu verwendeten Emulgatoren lassen sich für die verschiedensten Zwecke einsetzen, insbesondere in der Kosmetik, z. B. zur Cremeherstellung, in der Pharmazie, zur Schädlingsbekämpfung oder in der Textilindustrie. The emulsifiers to be used according to the invention can be used for use a wide variety of purposes, especially in cosmetics, z. B. for cream production, in the pharmaceutical industry, for pest control or in the textile industry.
Das Wasserbindevermögen der erfindungsgemäß zu verwendenden Emulgatoren
gegenüber dem aus dem Stand der Technik bekannten wurde an einer Mischung aus 90
Teilen Vaselin mit 10 Teilen Emulgatoren bestimmt: -Tabelle 1
Tabelle 2
Claims (1)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC29920A DE1215730B (en) | 1963-05-11 | 1963-05-11 | Process for preparing water-in-oil emulsions |
| GB17320/64A GB1038015A (en) | 1963-05-11 | 1964-04-27 | Water-in-oil emulsifier |
| CH561764A CH461533A (en) | 1963-05-11 | 1964-04-29 | Process for the production of water-in-oil emulsions |
| FR973576A FR1405879A (en) | 1963-05-11 | 1964-05-06 | water-in-oil emulsifiers |
| NL6405040A NL6405040A (en) | 1963-05-11 | 1964-05-06 | |
| BE647684A BE647684A (en) | 1963-05-11 | 1964-05-08 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC29920A DE1215730B (en) | 1963-05-11 | 1963-05-11 | Process for preparing water-in-oil emulsions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1215730B true DE1215730B (en) | 1966-05-05 |
Family
ID=7019146
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEC29920A Pending DE1215730B (en) | 1963-05-11 | 1963-05-11 | Process for preparing water-in-oil emulsions |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE647684A (en) |
| CH (1) | CH461533A (en) |
| DE (1) | DE1215730B (en) |
| GB (1) | GB1038015A (en) |
| NL (1) | NL6405040A (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2738333A (en) * | 1950-11-06 | 1956-03-13 | Colgate Palmolive Co | Surface-active compounds and detergent compositions containing same |
| DE1122938B (en) * | 1957-04-08 | 1962-02-01 | Chem Fab Dueren G M B H | Process for the production of sulfuric acid and phosphoric acid esters or their salts |
-
1963
- 1963-05-11 DE DEC29920A patent/DE1215730B/en active Pending
-
1964
- 1964-04-27 GB GB17320/64A patent/GB1038015A/en not_active Expired
- 1964-04-29 CH CH561764A patent/CH461533A/en unknown
- 1964-05-06 NL NL6405040A patent/NL6405040A/xx unknown
- 1964-05-08 BE BE647684A patent/BE647684A/xx unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2738333A (en) * | 1950-11-06 | 1956-03-13 | Colgate Palmolive Co | Surface-active compounds and detergent compositions containing same |
| DE1122938B (en) * | 1957-04-08 | 1962-02-01 | Chem Fab Dueren G M B H | Process for the production of sulfuric acid and phosphoric acid esters or their salts |
Also Published As
| Publication number | Publication date |
|---|---|
| BE647684A (en) | 1964-11-09 |
| NL6405040A (en) | 1964-11-12 |
| CH461533A (en) | 1968-08-31 |
| GB1038015A (en) | 1966-08-03 |
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