GB962919A - Process for the preparation of emulsifiers for ointment base compositions - Google Patents
Process for the preparation of emulsifiers for ointment base compositionsInfo
- Publication number
- GB962919A GB962919A GB28330/61A GB2833061A GB962919A GB 962919 A GB962919 A GB 962919A GB 28330/61 A GB28330/61 A GB 28330/61A GB 2833061 A GB2833061 A GB 2833061A GB 962919 A GB962919 A GB 962919A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ester
- pentaerythritol
- citric acid
- acid
- oil fatty
- 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
- 239000003883 ointment base Substances 0.000 title abstract 4
- 239000003995 emulsifying agent Substances 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 2
- 239000000203 mixture Substances 0.000 title 1
- -1 alcohol ester Chemical class 0.000 abstract 20
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 abstract 11
- 150000002148 esters Chemical class 0.000 abstract 10
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 8
- 229930195729 fatty acid Natural products 0.000 abstract 8
- 239000000194 fatty acid Substances 0.000 abstract 8
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 abstract 7
- 239000003921 oil Substances 0.000 abstract 6
- MUURADZHQSPGFN-UHFFFAOYSA-N 4-dodecoxy-2-(2-dodecoxy-2-oxoethyl)-2-hydroxy-4-oxobutanoic acid Chemical compound CCCCCCCCCCCCOC(=O)CC(O)(C(O)=O)CC(=O)OCCCCCCCCCCCC MUURADZHQSPGFN-UHFFFAOYSA-N 0.000 abstract 5
- 239000002253 acid Substances 0.000 abstract 5
- IMQYZLJIDNYQLX-UHFFFAOYSA-N 2-hydroxy-4-octadecoxy-2-(2-octadecoxy-2-oxoethyl)-4-oxobutanoic acid Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CC(O)(C(O)=O)CC(=O)OCCCCCCCCCCCCCCCCCC IMQYZLJIDNYQLX-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- 239000003240 coconut oil Substances 0.000 abstract 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 abstract 2
- 238000009884 interesterification Methods 0.000 abstract 2
- 239000012188 paraffin wax Substances 0.000 abstract 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 abstract 1
- CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical compound [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 abstract 1
- 229960000541 cetyl alcohol Drugs 0.000 abstract 1
- SASYSVUEVMOWPL-NXVVXOECSA-N decyl oleate Chemical compound CCCCCCCCCCOC(=O)CCCCCCC\C=C/CCCCCCCC SASYSVUEVMOWPL-NXVVXOECSA-N 0.000 abstract 1
- 239000012186 ozocerite Substances 0.000 abstract 1
- 229940099259 vaseline Drugs 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- 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
- 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
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty 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
- A61K8/375—Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
-
- 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
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
- C07C69/675—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids of saturated hydroxy-carboxylic acids
- C07C69/704—Citric acid esters
-
- 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
-
- 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
-
- 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
- C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
- C11C3/10—Ester interchange
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Materials Engineering (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Wood Science & Technology (AREA)
- Emergency Medicine (AREA)
- Birds (AREA)
- Medicinal Preparation (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Mixed esters are prepared by an interesterification process from a citric acid difatty alcohol ester and a pentaerythritol difatty acid ester in the molar ratio of 1:1. The citric acid ester is prepared at 140-170 DEG C. under a pressure of about 25 mm Hg by the addition to the alcohol of only as much aqueous citric acid as reacts simultaneously with the alcohol. Examples describe the preparation of a citric acid dioctadecyl ester, and a pentaerythritol di-coconut oil fatty acid ester and a mixed ester therefrom. Citric acid dilauryl ester and pentaerythritoldistearic acid ester, or pentaerythritol dicoconut oil fatty acid ester; citric acid-di-Guerbet (C22) alcohol ester and pentaerythritol distearic acid ester; citric acid-dioctadecanediol ester and pentaerythritol dicoconut oil fatty acid ester; citric acid-dioctadecanediol ester and pentaerythritol distearic acid ester; citric acid-didodecyl ester and pentaerythritol dicoconut oil fatty acid ester are also mentioned and the products are heat stable, show improved water-binding properties, and are suitable for use as emulsifiers for ointment bases.ALSO:Emulsifiers for ointment bases comprise mixed esters prepared by the interesterification of a citric acid difatty alcohol ester and a pentaerythritol difatty acid ester in a molar ratio of 1 : 1. The preparation of a mixed ester of a citric acid dioctadecyl ester and a pentaerythritol di-coconut oil fatty acid ester is described and it is used in an ointment base with "Vaseline" (Registered Trade Mark), decyl oleate, cetyl alcohol, ozocerite, hard paraffin, viscous paraffin, and aluminium stearate. Mixed esters of citric acid-dilauryl ester and pentaerythritol-distearric acid ester; citric acid-dilauryl ester and pentaerythritol-dicoconut oil fatty acid ester, citric acid-di-Guerbet (C22) alcohol ester and pentaerythritol-distearic acid ester; citric acid-dioctadecanediol ester and pentaerythritol-dicoconut oil fatty acid ester; citric acid-dioctadecanediol ester and pentaerythritoldistearic acid ester; and citric acid-didodecyl ester and pentaerythritol-dicoconut oil fatty acid ester are also mentioned.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DED33979A DE1165574B (en) | 1960-08-08 | 1960-08-08 | Process for the production of mixed esters used as emulsifiers for ointment bases |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB962919A true GB962919A (en) | 1964-07-08 |
Family
ID=7041984
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB28330/61A Expired GB962919A (en) | 1960-08-08 | 1961-08-04 | Process for the preparation of emulsifiers for ointment base compositions |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE639411A (en) |
| CH (1) | CH397633A (en) |
| DE (1) | DE1165574B (en) |
| GB (1) | GB962919A (en) |
| NL (1) | NL267914A (en) |
Cited By (85)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6033652A (en) * | 1996-05-15 | 2000-03-07 | Henkel Kommanditgesellschaft Auf Aktien | Hair-treatment formulations |
| US6121331A (en) * | 1996-06-07 | 2000-09-19 | Henkel Kommanditgesellschaft Auf Aktien | Aqueous nacreous luster concentrates |
| US6207140B1 (en) | 1996-10-07 | 2001-03-27 | Cognis Deutschland Gmbh | Sun screening agents in the form of oil/water micro emulsions |
| US6210659B1 (en) | 1996-11-13 | 2001-04-03 | Henkel Kommanditgesellschaft Auf Aktien | Aqueous pearlescing concentrates |
| US6221370B1 (en) | 1996-09-02 | 2001-04-24 | Henkel Kommanditgesellschaft Auf Aktien | Fatty acid ethoxylates and partial glycerides for preparing phase inversion temperature emulsions |
| US6228831B1 (en) | 1996-06-07 | 2001-05-08 | Henkel Kommanditgesellschaft Auf Aktien | Aqueous nacreous lustre concentrates |
| US6235702B1 (en) | 1996-05-30 | 2001-05-22 | Henkel Kommaditgesellschaft Auf Aktien | Aqueous nacreous lustre concentrate |
| US6280712B1 (en) | 1997-08-29 | 2001-08-28 | Cognis Deutschland Gmbh | Sun screen agents |
| US6300297B1 (en) | 1997-08-25 | 2001-10-09 | Cognis Deutschland Gmbh | Hard soap containing fatty acid polyglycol ester sulphates |
| US6306410B1 (en) | 1997-09-24 | 2001-10-23 | Cognis Deutschland Gmbh | Cosmetic formulations containing ethoxylated partial glycerides |
| US6309628B1 (en) | 1996-11-13 | 2001-10-30 | Henkel Kommanditgesellschaft Auf Aktien | Pearlescent cosmetic preparations containing dialkyl ethers, silicone compounds and emulsifier |
| US6313085B1 (en) | 1999-06-29 | 2001-11-06 | Cognis Deutschland Gmbh | High-concentration flowable anionic surfactant mixtures containing alkyl ether sulfates and alkyl sulfates |
| US6333040B1 (en) | 1997-03-19 | 2001-12-25 | Henkel Kommanditgesellschaft Auf Aktien | Cosmetic preparations |
| US6348202B1 (en) | 1996-12-05 | 2002-02-19 | Henkel Kommanditgesellschaft Auf Aktien | Cosmetic compositions containing dihydroxyacetone and methods of stabilizing the same |
| US6362142B1 (en) | 1997-07-17 | 2002-03-26 | Cognis Deutschland Gmbh | Detergent mixtures containing ester quats, chitosan and/or chitosan derivatives and protein hydrolyzates |
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| US6432419B2 (en) | 1996-06-12 | 2002-08-13 | Cognis Deutschland Gmbh | Use of fats to replace silicone in cosmetic and/or pharmaceutical preparations |
| US6479618B1 (en) | 1998-12-10 | 2002-11-12 | Cognis Deutschland Gmbh | Enzymatic esterification |
| US6482418B1 (en) | 1996-06-12 | 2002-11-19 | Henkel Kommanditgesellschaft Auf Aktien | Cosmetic and/or pharmaceutical preparations comprising dialkenyl carbonates |
| US6494920B1 (en) | 1999-02-04 | 2002-12-17 | Cognis Deutschland Gmbh & Co. Kg | Detergent mixtures |
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| US6569410B1 (en) | 1999-04-10 | 2003-05-27 | Cognis Deutschland Gmbh | Sun protection compositions containing UV protection factors and esters of hydroxycarboxylic acids and alk(en)yl oligoglycosides |
| US6572663B1 (en) | 1997-12-13 | 2003-06-03 | Cognis Deutschland Gmbh & Co. Kg | Method for producing hair coloring preparations with improved viscosity |
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| US6586379B1 (en) | 1998-10-02 | 2003-07-01 | Cognis Deutschland Gmbh | Syndet soap bars comprising olefin sulfonate |
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| US6616706B1 (en) | 1997-05-12 | 2003-09-09 | Henkel Kommanditgesellschaft Auf Aktien | Method for producing hair dye products |
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| DE860204C (en) * | 1941-06-22 | 1952-12-18 | Hydrierwerke A G Deutsche | Process for the preparation of ester-like condensation products |
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1960
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- 1961-08-04 NL NL267914A patent/NL267914A/en unknown
- 1961-08-04 GB GB28330/61A patent/GB962919A/en not_active Expired
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| US10941370B2 (en) | 2014-07-25 | 2021-03-09 | Henkel Ag & Co. Kgaa | Transparent textile care agent |
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Also Published As
| Publication number | Publication date |
|---|---|
| BE639411A (en) | 1964-02-17 |
| CH397633A (en) | 1965-08-31 |
| DE1165574B (en) | 1964-03-19 |
| NL267914A (en) | 1964-06-25 |
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