GB854925A - Improvements in or relating to phosphatide emulsifying agents - Google Patents
Improvements in or relating to phosphatide emulsifying agentsInfo
- Publication number
- GB854925A GB854925A GB16287/57A GB1628757A GB854925A GB 854925 A GB854925 A GB 854925A GB 16287/57 A GB16287/57 A GB 16287/57A GB 1628757 A GB1628757 A GB 1628757A GB 854925 A GB854925 A GB 854925A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phosphatide
- oxide
- oxyalkylated
- ethylene oxide
- soybean
- 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
- 239000003995 emulsifying agent Substances 0.000 title abstract 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract 4
- 235000010469 Glycine max Nutrition 0.000 abstract 4
- 244000068988 Glycine max Species 0.000 abstract 4
- 229910052740 iodine Inorganic materials 0.000 abstract 4
- 239000011630 iodine Substances 0.000 abstract 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- 239000003795 chemical substances by application Substances 0.000 abstract 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 238000007911 parenteral administration Methods 0.000 abstract 2
- 239000000047 product Substances 0.000 abstract 2
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 abstract 2
- LRYZPFWEZHSTHD-HEFFAWAOSA-O 2-[[(e,2s,3r)-2-formamido-3-hydroxyoctadec-4-enoxy]-hydroxyphosphoryl]oxyethyl-trimethylazanium Chemical class CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](NC=O)COP(O)(=O)OCC[N+](C)(C)C LRYZPFWEZHSTHD-HEFFAWAOSA-O 0.000 abstract 1
- AAMHBRRZYSORSH-UHFFFAOYSA-N 2-octyloxirane Chemical compound CCCCCCCCC1CO1 AAMHBRRZYSORSH-UHFFFAOYSA-N 0.000 abstract 1
- GJEZBVHHZQAEDB-UHFFFAOYSA-N 6-oxabicyclo[3.1.0]hexane Chemical compound C1CCC2OC21 GJEZBVHHZQAEDB-UHFFFAOYSA-N 0.000 abstract 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 abstract 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 abstract 1
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 abstract 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 abstract 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 abstract 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 1
- 229940087168 alpha tocopherol Drugs 0.000 abstract 1
- 239000003963 antioxidant agent Substances 0.000 abstract 1
- 230000003078 antioxidant effect Effects 0.000 abstract 1
- 235000006708 antioxidants Nutrition 0.000 abstract 1
- 239000012736 aqueous medium Substances 0.000 abstract 1
- 239000007900 aqueous suspension Substances 0.000 abstract 1
- 150000001720 carbohydrates Chemical class 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 235000019864 coconut oil Nutrition 0.000 abstract 1
- 239000003240 coconut oil Substances 0.000 abstract 1
- 230000000052 comparative effect Effects 0.000 abstract 1
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 abstract 1
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- -1 glucose Chemical class 0.000 abstract 1
- 239000008103 glucose Substances 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 239000000787 lecithin Substances 0.000 abstract 1
- 235000010445 lecithin Nutrition 0.000 abstract 1
- 239000002960 lipid emulsion Substances 0.000 abstract 1
- 239000002609 medium Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000003921 oil Substances 0.000 abstract 1
- 235000019198 oils Nutrition 0.000 abstract 1
- 239000002574 poison Substances 0.000 abstract 1
- 231100000614 poison Toxicity 0.000 abstract 1
- 239000012429 reaction media Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
- 229960000984 tocofersolan Drugs 0.000 abstract 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 abstract 1
- 239000002076 α-tocopherol Substances 0.000 abstract 1
- 235000004835 α-tocopherol Nutrition 0.000 abstract 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
- C09K23/14—Derivatives of phosphoric acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/10—Phosphatides, e.g. lecithin
- C07F9/103—Extraction or purification by physical or chemical treatment of natural phosphatides; Preparation of compositions containing phosphatides of unknown structure
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23J—PROTEIN COMPOSITIONS FOR FOODSTUFFS; WORKING-UP PROTEINS FOR FOODSTUFFS; PHOSPHATIDE COMPOSITIONS FOR FOODSTUFFS
- A23J7/00—Phosphatide compositions for foodstuffs, e.g. lecithin
-
- 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
- A61K47/24—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing atoms other than carbon, hydrogen, oxygen, halogen, nitrogen or sulfur, e.g. cyclomethicone or phospholipids
-
- 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
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
Abstract
The invention comprises an oxyalkylated phosphatide, the phosphatide prior to oxyalkylation having an iodine number of from 30 to 60 and demonstrating a cloud point of not more than 60 DEG C. The oxyalkylated phosphatide may be obtained by treating a crude phosphatide to separate at least a portion of the hydrogenation catalyst poisons present, hydrogenating the separated phosphatide to an iodine number of from 30 to 60, e.g. by the process described in Specification 825,936, and then reacting the product with an oxyalkylating agent. The phosphatide may be derived from lecithins, cephalins or sphingomyelins and particularly from crude soybean phosphatide. Specified oxyalkylating agents are ethylene oxide, propylene oxide, butylene oxide, decene oxide, styrene oxide, epichlorhydrin, glycide, cyclohexene oxide and cyclopentene oxide. The oxyalkyation may be effected in any suitable solvent medium and an aqueous suspension of the phosphatide is suitably used. The amount of oxyalkylating agent reacted with the phosphatide is preferably such as to raise the pH of a 5% aqueous W/V suspension to from 5,5 to 8,0 and more preferably to from 6,9 to 7,2. Any excess ethylene oxide (when used) can be expelled from the reaction product by heating to about 80 DEG C. for about 20 minutes. An example is given for the oxyethylation of a soybean phosphatide (iodine value about 52 and cloud point 32 DEG C.) in aqueous medium using gaseous ethylene oxide in such amount as to increase the initial pH of 5,8 to 6,7. Examples are also given in which cyclohexane or a mixture of cyclohexane and methanol are used instead of water as reaction medium in a similar oxyethylation process and a comparative example is included in which commercial soybean phosphatide is oxyalkylated with ethylene oxide. The products are suitable as emulsifying agents in oil and water emulsions for parenteral administration (see Group VI). Specification 770,427 also is referred to.ALSO:A fat emulsion suitable for parenteral administration comprises an injectable trigylceride emulsified with water and containing as an emulsifying agent an oxyalkylated phosphatide (especially soybean phosphatide), the phosphatide (prior to oxyalkylation) having an iodine number of from 30 to 60 and demonstrating a cloud point of not more than 60 DEG C. (see Group IV(b)). The injectable triglyceride is suitably a refined, edible coconut oil and a metabolisable carbohydrate e.g. glucose, and an anti-oxidant e.g. alphatocopherol may also be present. Specifications 770,427 and 825,936 are referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US854925XA | 1956-05-23 | 1956-05-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB854925A true GB854925A (en) | 1960-11-23 |
Family
ID=22191962
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB16287/57A Expired GB854925A (en) | 1956-05-23 | 1957-05-22 | Improvements in or relating to phosphatide emulsifying agents |
Country Status (2)
| Country | Link |
|---|---|
| FR (1) | FR1175676A (en) |
| GB (1) | GB854925A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4104403A (en) * | 1976-12-21 | 1978-08-01 | Witco Chemical Corporation | Water-oil emulsions and method of preparing same |
-
1957
- 1957-05-22 GB GB16287/57A patent/GB854925A/en not_active Expired
- 1957-05-22 FR FR1175676D patent/FR1175676A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4104403A (en) * | 1976-12-21 | 1978-08-01 | Witco Chemical Corporation | Water-oil emulsions and method of preparing same |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1175676A (en) | 1959-03-31 |
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