CA2111773A1 - Phospholipid composition - Google Patents
Phospholipid compositionInfo
- Publication number
- CA2111773A1 CA2111773A1 CA002111773A CA2111773A CA2111773A1 CA 2111773 A1 CA2111773 A1 CA 2111773A1 CA 002111773 A CA002111773 A CA 002111773A CA 2111773 A CA2111773 A CA 2111773A CA 2111773 A1 CA2111773 A1 CA 2111773A1
- Authority
- CA
- Canada
- Prior art keywords
- weight
- composition
- phospholipid
- phospholipid composition
- acylphosphatidylethanolamine
- 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.)
- Abandoned
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/66—Phosphorus compounds
-
- 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
- A61K8/34—Alcohols
-
- 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
- A61K8/34—Alcohols
- A61K8/345—Alcohols containing more than one hydroxy group
-
- 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
- A61K8/18—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
- A61K8/41—Amines
-
- 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
- A61K8/55—Phosphorus compounds
- A61K8/553—Phospholipids, e.g. lecithin
-
- 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
- A61K8/67—Vitamins
- A61K8/676—Ascorbic acid, i.e. vitamin C
-
- 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
- A61K8/67—Vitamins
- A61K8/678—Tocopherol, i.e. vitamin E
-
- 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
- A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
- A61K8/922—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of vegetable origin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q13/00—Formulations or additives for perfume preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/02—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings containing insect repellants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/52—Stabilizers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/74—Biological properties of particular ingredients
- A61K2800/75—Anti-irritant
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Dermatology (AREA)
- Emergency Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Molecular Biology (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Biophysics (AREA)
- Cosmetics (AREA)
- Medicinal Preparation (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Fats And Perfumes (AREA)
Abstract
Abstract A novel phospholipid preparation is described, which comprises at least 20 % by weight phosphatidylcholine, at least 20 % by weight N-acylphosphatidylethanolamine, as well as less than 3 % by weight phosphatidylethanolamine, besides the usual ingredients.
A process for the production of the phospholipid composition uses acylated crudelecthin as starting material, which is treated with methanol.
After the separation of the sediment the phospholipid composition is isolated from the methanol extract.
A process for the production of the phospholipid composition uses acylated crudelecthin as starting material, which is treated with methanol.
After the separation of the sediment the phospholipid composition is isolated from the methanol extract.
Description
21117'13 Phospholipid composilion.
s The present invention relates to a phospholipid composition with the characteristic features of the generic part of claim 1, as well as a process for the production of such a phospholipid composition with the characteristic features of the generic part of claim 1 1 . , Phospholipid compositions appear in nature in different chemical forms. For instance, phospholipid compositions can be isolated from animal starting matetials, like for instance eggs. Additionally plant sources like coconut-copra, palm kernels, earth nuts, rape, sun-flower, olives or in particular soybean may be used to obtain the 15 phospholipid compositions.
To produce the phospholipid composition from the above-mentioned plant material the respective oil is degummed, for instance by the treatment with small quantities of steam or water. The resulting phospholipid composition also called degummed 20 lecithin, usually provides between 8 % by weight and 59 % by weight phospholipids.
After drying, a product is obtained which is called a crude lecithin.
Depending on the respective starting material from which the degununed lecithin was isolated, its chemical composition varies. The most important crude lecithin, which is 25 isolated from soybean and is accordingly called soybean lecithin, comprises according to PARDUN (Pardun H., Die Pflanzenlecithine, Verlag fur Chem. Industrie H.Ziolkowsly, 1988) -~ ~ 30 %byweight - 35 %byweight triglycerides 2 %byweight - 5 %byweight freefattyacids, sterols, tocopheroles, 11 %byweight - 17 %byweight glycolipids,carbohydrates, 48 %byweight - 55 -%byweight phospholipidsand 0,2 %byweight - 0,7 %byweight water.
.~
30 It can be taken from the previously presented chemical composition, that the phospholipids are with their 48 % by weight to appr. 55 % by weight me main ~, component of phospholipid compositions. The phospholipids in crude lecithin are mainly phosphatidylcholine, phosphatidylethanolamine, and phosphatidylinositol, the amounts of these three main components varying as follows, relative to the mass of the - 3s crude lecithin:
12 % by weight - 18 % by weight phosphatidylcholine, 9 % by weight - 15 % by weight phosphatidylethanolamine and 8 % by weight - 12 % by weight phosphatidylinositol.
Besides these main components crude soybean lecithin further comprises Iysophosphatidylcholine, Iysophosphatidylethanolamine, phosphatidic acid as well as , .- . ~ . . .. , .. - .
2 2111'~ ~3 nl-acylphospllatidylethanolamine as further phospholipid inL~redients, the concentr~tion of N-acylphospllatidylethanolamine varying between I % by weight and 3 % by weight, relative to the mass of the crude soybean lecithin.
5 The previously mentioned crude lecithin can, depending on the intended use, befurther processed. One of the possibilities is to remove the oil from the crude lecithin by a treatment with acetone. Such an acetone treatment removes most of the neutral lipids, leading to an increase in phosphatidylcholine content in this purified lecithin to a value between 25 % by weight and 30 % by weight .
A further possibility is an acylation of degummed lecithin, which as was said before is produced from plant oil by the treatment with small quantities of steam or water, with acid anhydrides. After drying these acylated lecithins provide the following composition of the phospholipid ingredients 12 % by weight - 18 % by weight phosphatidylcholine, 3 % by weight - 5 % by weight phosphatidylethanolamine, 6 % by weight - 10% by weight N-acylphosphatidylethanolamine and 8 % by weight - 12 % by weight phosphatidylinositol.
Furthermore the acylated lecithin comprises small quantities of the previously mentioned further phospholipid ingredients.
The above-mentioned acylated lecithins have a limited place in pharmaceutical and 25 cosmetic technology. This relates to the danger, that cosmetic or pharmaceutical preparations containing them age fairly rapidly, which expresses itself in unwanted changes in taste, colour and/or smell The aim of the present invention was to provide a phospholipid composition, which is 30 suitable for the preparation of stable edible products, luxury products, cosmetics and/or pharmaceutical products.
The aim is reached according to the present invention by a phospholipid composition with the characteristic features of the characteristic part of claim 1.
3s The subject pbospholipid composition with a content of at least 20 % by weight phosphatidylcholine further comprises besides the usual ingredients at least 20 % by weight N-acylphosphatidylethanolamine as well as less than 3 % by weight phosphatidylethanolamine.
Surprisingly it could be observed, that the afore-mentioned phospholipid composition is excellently suited for the production of foodstuffs, luxury products, cosmetics and/or pharmaceutical products, since the produced foodstuffs, luxury products, cosmetics and/or pharmaceuticals provide a substantial stability, which could be achieved only 45 to a limited extent with the conventional acylated phospholipids. A further obvious advantage of the subject phospholipid composition is the fact that the foodstuffs, luxury products, cosmetics and/or pharmaceuticals, which have been produced fromit, do not show any changes in smell andlor taste. The reason of this improvement is !, ~ ................................... . :
;..... . : - ' 21~773 thought to be the fact, that in the subject composition the concentration of phosphatidylethanolamine is kept wilfully at a very low level, namely less than 3% I~y weight . Such a low content in phosphatidylethnnolamine prevents unwanted reactions between the phosphatidylethanolamine itself and the flavours and the active 5 ingredients present in the foodstuffs, luxury products, cosmetics and/or pharmaceuticals, so that when the phospholipid composltion is used to produce the foodstuffs, luxury products, cosmetics and/or pharmaceuticals, no reaction products of the phosphatidylethanolamine with the active ingredients and/or flavours can be generated. It is obvious, that since no reaction or hardly any reaction takes place o between the phosphatidylethanolamine contained in the inventive phosholipid composition and the active ingredients or the flavours, they are not inactivated durinL~
the production and/or storage of the foodstuffs, luxury products, cosmetics and/or pharmaceutical products, which explains the increased efficacy and improved storage stability of the foodstuffs, luxury products, cosmetics and pharmaceutical products 15 manufactured with the inventive phospholipid composition. During the production phase of the above products, the use of the subject composition prevents any unwanted colour changes in the final products and this colour stability continues to be present during storage of such products over long periods of time.
Again this colour stability is explained by the fact that no reaction takes place between 20 the phosphatidylethanolamine and the respective ingredients of the foodstuffs, luxury products, cosmetics and/or pharmaceuticals.
An additional phenomenon is the apparent inhibition by the inventive phospho1ipid composition of the oxidation of the foodstuffs, luxury products, cosmetics and/or pharmaceuticals, this protection against oxidation being due to the presence of the high 25 content in N-acylphosphatidylethanolamine.
The subject phospholipid composition provides further advantages. It could be observed, that it was perfectly suited as dispersifier or emulsifier and enabled the preparation of excellent dispersions or emulsions from a large number of excipients or 30 active ingredients used in foodstuffs, luxury products, cosmetics and/or pharmaceuticals. Correspondingly prepared emulsions and dispersions, which may be oil-in-water emulsions as well as water-in-oil emulsions, do not show any separating phenomena not even after extremely long storage and provide for instance to fluid or pasty foodstuffs, luxury products, cosmetics and/or pharmaceutical preparations, over 3s a long period of time a stable consistency. Furthermore, the topical use of the subject composition does not provoke any skin irritation or skin erythema even in the most sensitive users, which makes the subject composition perfectly suited to be used as base material in the production of topical cosmetics or pharmaceuticals in the form of ointments, creams, shampoos, or others.
Apart from the phosphatidylcholine, the N-acylphosphatidylethanolamine and the phosphatidylethanolamine the subject phospholipid composition further provides as usual ingredients, such ingredients, which have been listed at the beginning of the description under specification of their weight ranges, namely the triglycerides, free 45 fatty acids, sterols, tocopheroles, glycolipids, carbohydrates and water. Further the subject phospholipid composition comprises other phospholipids like for instanceIysophosphatidylcholine, Iysophosphatidylethanolamine, phosphatidic acid and/or their derivatives.
. .
, ... . . ... .. ., ~ . , .
i; . - . ~ . .
~ !, . .:
,.... .
s The present invention relates to a phospholipid composition with the characteristic features of the generic part of claim 1, as well as a process for the production of such a phospholipid composition with the characteristic features of the generic part of claim 1 1 . , Phospholipid compositions appear in nature in different chemical forms. For instance, phospholipid compositions can be isolated from animal starting matetials, like for instance eggs. Additionally plant sources like coconut-copra, palm kernels, earth nuts, rape, sun-flower, olives or in particular soybean may be used to obtain the 15 phospholipid compositions.
To produce the phospholipid composition from the above-mentioned plant material the respective oil is degummed, for instance by the treatment with small quantities of steam or water. The resulting phospholipid composition also called degummed 20 lecithin, usually provides between 8 % by weight and 59 % by weight phospholipids.
After drying, a product is obtained which is called a crude lecithin.
Depending on the respective starting material from which the degununed lecithin was isolated, its chemical composition varies. The most important crude lecithin, which is 25 isolated from soybean and is accordingly called soybean lecithin, comprises according to PARDUN (Pardun H., Die Pflanzenlecithine, Verlag fur Chem. Industrie H.Ziolkowsly, 1988) -~ ~ 30 %byweight - 35 %byweight triglycerides 2 %byweight - 5 %byweight freefattyacids, sterols, tocopheroles, 11 %byweight - 17 %byweight glycolipids,carbohydrates, 48 %byweight - 55 -%byweight phospholipidsand 0,2 %byweight - 0,7 %byweight water.
.~
30 It can be taken from the previously presented chemical composition, that the phospholipids are with their 48 % by weight to appr. 55 % by weight me main ~, component of phospholipid compositions. The phospholipids in crude lecithin are mainly phosphatidylcholine, phosphatidylethanolamine, and phosphatidylinositol, the amounts of these three main components varying as follows, relative to the mass of the - 3s crude lecithin:
12 % by weight - 18 % by weight phosphatidylcholine, 9 % by weight - 15 % by weight phosphatidylethanolamine and 8 % by weight - 12 % by weight phosphatidylinositol.
Besides these main components crude soybean lecithin further comprises Iysophosphatidylcholine, Iysophosphatidylethanolamine, phosphatidic acid as well as , .- . ~ . . .. , .. - .
2 2111'~ ~3 nl-acylphospllatidylethanolamine as further phospholipid inL~redients, the concentr~tion of N-acylphospllatidylethanolamine varying between I % by weight and 3 % by weight, relative to the mass of the crude soybean lecithin.
5 The previously mentioned crude lecithin can, depending on the intended use, befurther processed. One of the possibilities is to remove the oil from the crude lecithin by a treatment with acetone. Such an acetone treatment removes most of the neutral lipids, leading to an increase in phosphatidylcholine content in this purified lecithin to a value between 25 % by weight and 30 % by weight .
A further possibility is an acylation of degummed lecithin, which as was said before is produced from plant oil by the treatment with small quantities of steam or water, with acid anhydrides. After drying these acylated lecithins provide the following composition of the phospholipid ingredients 12 % by weight - 18 % by weight phosphatidylcholine, 3 % by weight - 5 % by weight phosphatidylethanolamine, 6 % by weight - 10% by weight N-acylphosphatidylethanolamine and 8 % by weight - 12 % by weight phosphatidylinositol.
Furthermore the acylated lecithin comprises small quantities of the previously mentioned further phospholipid ingredients.
The above-mentioned acylated lecithins have a limited place in pharmaceutical and 25 cosmetic technology. This relates to the danger, that cosmetic or pharmaceutical preparations containing them age fairly rapidly, which expresses itself in unwanted changes in taste, colour and/or smell The aim of the present invention was to provide a phospholipid composition, which is 30 suitable for the preparation of stable edible products, luxury products, cosmetics and/or pharmaceutical products.
The aim is reached according to the present invention by a phospholipid composition with the characteristic features of the characteristic part of claim 1.
3s The subject pbospholipid composition with a content of at least 20 % by weight phosphatidylcholine further comprises besides the usual ingredients at least 20 % by weight N-acylphosphatidylethanolamine as well as less than 3 % by weight phosphatidylethanolamine.
Surprisingly it could be observed, that the afore-mentioned phospholipid composition is excellently suited for the production of foodstuffs, luxury products, cosmetics and/or pharmaceutical products, since the produced foodstuffs, luxury products, cosmetics and/or pharmaceuticals provide a substantial stability, which could be achieved only 45 to a limited extent with the conventional acylated phospholipids. A further obvious advantage of the subject phospholipid composition is the fact that the foodstuffs, luxury products, cosmetics and/or pharmaceuticals, which have been produced fromit, do not show any changes in smell andlor taste. The reason of this improvement is !, ~ ................................... . :
;..... . : - ' 21~773 thought to be the fact, that in the subject composition the concentration of phosphatidylethanolamine is kept wilfully at a very low level, namely less than 3% I~y weight . Such a low content in phosphatidylethnnolamine prevents unwanted reactions between the phosphatidylethanolamine itself and the flavours and the active 5 ingredients present in the foodstuffs, luxury products, cosmetics and/or pharmaceuticals, so that when the phospholipid composltion is used to produce the foodstuffs, luxury products, cosmetics and/or pharmaceuticals, no reaction products of the phosphatidylethanolamine with the active ingredients and/or flavours can be generated. It is obvious, that since no reaction or hardly any reaction takes place o between the phosphatidylethanolamine contained in the inventive phosholipid composition and the active ingredients or the flavours, they are not inactivated durinL~
the production and/or storage of the foodstuffs, luxury products, cosmetics and/or pharmaceutical products, which explains the increased efficacy and improved storage stability of the foodstuffs, luxury products, cosmetics and pharmaceutical products 15 manufactured with the inventive phospholipid composition. During the production phase of the above products, the use of the subject composition prevents any unwanted colour changes in the final products and this colour stability continues to be present during storage of such products over long periods of time.
Again this colour stability is explained by the fact that no reaction takes place between 20 the phosphatidylethanolamine and the respective ingredients of the foodstuffs, luxury products, cosmetics and/or pharmaceuticals.
An additional phenomenon is the apparent inhibition by the inventive phospho1ipid composition of the oxidation of the foodstuffs, luxury products, cosmetics and/or pharmaceuticals, this protection against oxidation being due to the presence of the high 25 content in N-acylphosphatidylethanolamine.
The subject phospholipid composition provides further advantages. It could be observed, that it was perfectly suited as dispersifier or emulsifier and enabled the preparation of excellent dispersions or emulsions from a large number of excipients or 30 active ingredients used in foodstuffs, luxury products, cosmetics and/or pharmaceuticals. Correspondingly prepared emulsions and dispersions, which may be oil-in-water emulsions as well as water-in-oil emulsions, do not show any separating phenomena not even after extremely long storage and provide for instance to fluid or pasty foodstuffs, luxury products, cosmetics and/or pharmaceutical preparations, over 3s a long period of time a stable consistency. Furthermore, the topical use of the subject composition does not provoke any skin irritation or skin erythema even in the most sensitive users, which makes the subject composition perfectly suited to be used as base material in the production of topical cosmetics or pharmaceuticals in the form of ointments, creams, shampoos, or others.
Apart from the phosphatidylcholine, the N-acylphosphatidylethanolamine and the phosphatidylethanolamine the subject phospholipid composition further provides as usual ingredients, such ingredients, which have been listed at the beginning of the description under specification of their weight ranges, namely the triglycerides, free 45 fatty acids, sterols, tocopheroles, glycolipids, carbohydrates and water. Further the subject phospholipid composition comprises other phospholipids like for instanceIysophosphatidylcholine, Iysophosphatidylethanolamine, phosphatidic acid and/or their derivatives.
. .
, ... . . ... .. ., ~ . , .
i; . - . ~ . .
~ !, . .:
,.... .
4 2~ ~1773 The phosphatidylcholine concentration in the subject phospholipid composition must be higher than 20 % by weight, relative to the phospholipid composition. Preferal~ly however the phospholipid composition provides a phospholipid concentration of 5 between 22% by weight and 40% by weight, in particular between 25% by weight and 30% by weight, relative to the mass of the phospholipid composition.
The content in N-acylphosphatidylethanolamine in the subject phospholipid composition varies between ~1 % by weight and 40 % by weight, preferably betweeno 24 % by weight and 28 % by weight .
In order to prevent the previously described unwanted reactions between phosphatidylethanolamine and any further ingredient, a further particularly suitable embodiment of the phospholipid composition provides a composition with a s phosphatidylethanolamine content between 0,01 % and 1,5 % by weight . In particular when the phosphatidylethanolamine content is below I % by weight, relative to the phospholipid composition, then said unwanted reactions, which may lead to changes in smell and/or taste andtor which may lead to unwanted colour changes, are prevented.
20 Another embodiment of the subject composition provides, that the subject phospholipid composition comprises at least 30 % by weight negatively charged phospholipids, in particular N-acylphosphatidylethanolamine in the amount as stated before, phosphatidic acid at between appr. I % by weight and 3 % by weight, phosphatidylinositol at between appr. 2 % by weight and appr. 6 % by weight as well 25 as further negatively charged phospholipids, preferably salts of phosphatidylglycerol or its corresponding derivatives.
Due to its before-mentioned relatively high content in negatively charged phospholipids, such an embodiment is very effective to stabilise liposomes, produced 30 from phospholipid fractions, which contain a large concentration in phosphatidylcholine, in particular a concentration of at least 80% by weight andpreferably 90 % by weight .
A particularly suited and preferably used phospholipid composition according to the 35 invention comprises 25 %byweight - 30 %byweight phosphatidylcholine, 24 % by weight - 28 % by weight N-acylphosphatidylethanolamine, 0.01 % by weight - 1.5 % by weight phosphatidylethanolamine and 40.5 % by weight - 50.99 % by weight other ingredients.
The other ingredients of tbe above list may constitute the previously mentioned 40 ingredients, in particular triglycerides, free fatty acids, sterols, tocopheroles, glycolipids, carbohydrates or other phospholipids like for instance phosphatidic acid, Iysophosphatidylethanolamine, phosphatidylglycerol and/or their derivatives. Thepreviously mentioned embodiment of the subject phospholipid composition providesexcellent dispersing and emulsifying properties for a number of active ingredients or 21~1773 ingredients, making it a very appropriate product to be used in the production of foodstuffs, luxury products, cosmetics and/or pharmaceuticals. Furthermore, thisembodiment provides all advantages even in more pronounced form, as have been described before for the subject phospholipid composition.
In the previous text there was only spoken generally of N-acyl-phosphatidylethanolamine. Preferred products from this class of products are N-oleoylphosphatidylethanolamine, N-palmitoylphosphatidylethanolamine, N-stearylphosph?tidylethanolamine, N-miristoylphosphatidylethanolamine and/or N-o acetylphosphatidylethanolamine alone or as a mixture. Particularly preferred is anembodiment, which contains N-acylphosphatidylethanolamine consisting to at least 90 % by weight of N-acetylphosphatidylethanolamine. This specific embodiment is particularly suitable for the use in pharmaceutical and/or cosmetic preparations for topical use, since in particular N-acetylphosphatidylethanolamine is highly efficacious s in the prevention of skin irritations and eye irritations and furthermore possesses a therapeutic quality towards skin inflammations and/or skin damage. This phenomenon has been described extensively in the German patent applications P 42 42 959.5 and P
42 42 960.9.
20 All concentrations which have been cited in the present specification in connection with the inventive phospholipid composition especially for phosphatidylcholine, N-acylphosphatidylethano1amine and phosphatidylethanolamine were relative to a solid, undiluted phospho1ipid composition. This would mean the solid phospholipid composition to be used as such. For special cases it is to be recommended, in view of a 25 better handling, to use liquid formulations of the phospholipid composition, preferably so1utions of the subject phospholipid composition. Different solvents may be used depending on the specific chemical structure of the phospholipid compositions, so for instance Cl-C4-alcohols, mono-or diglycerides and/or poly-alcohols, so1utions inpropylene glycol being preferred. To prepare such solutions of the subject 30 phospholipid composition, 70 % by weight to 90 % by weight of the previously described subject phospholipid composition, comprising at least 20 % by weight phosphatidylcholine, at least 20 % by weight N-acylphosphatidylethanolamine and less than 3 % by weight phosphatidylethanolamine are dissolved in 30 % by weightto 10% by weight of propylene glycol.
The subject invention further relates to a process for the production of the previously described phospholipid composition.
The subject process for the production of the previously described phospholipid 40 composition utilises as starting material an acylated crude phosphatide, treats the crude phosphatide with methanol and isolates the methanol-soluble fraction.
The subject method distinguishes itself by the major advantage, that it is simple to perform and with a relatively simple apparatus. Use of the inventive method for the 45 manufacturing of the previously described inventive phospholipid composition results in short production times and as a consequence against a low cost price, the final phospholipid composition containing at least 20 % by weight N-acyl-phosphatidylethanolamine and less than 3 % by weight phosphatidylethanolamine, as 6 2~il773 .
well as the usual ingredients, like free fatty acids, sterols, tocopheroles, glycolipi<ls, carbohydrates, water, other phospholipids, in particular lysophosphati(lylcholille, Iysophosphatidylethanolamine, phosphatidic acid and/or phosphatidylglycerol.
5 A preferred starting mnterial for the subject invention is the lype of acylated crude phosphatide, which is obtained by acylation of crude soybean lecithin accordin~ to known methods, for instance described by PARDUN ( Pardun, Die Pflanzenlecithine,Verlag fur chemische Industrie, H.Ziolkowsky KG, Augsburg, 1988).
o In order to prevent any unwanted change in the used acylated crude phosphatideduring the treatment with the methanol and in particular to warrant, that the fraction isolated with methanol from the crude lecithin provides the chemical structure which was described above for the subject phospholipid composition, the treatment is preferably performed at room temperature, at a temperature range between 5 C and 5 35 C, in particular between 10 C and lS C. It is evident, that a higher temperature range may be selected, for instance between 35 C and 60 C, but the risk at such increased temperatures is connected with the danger, that unwanted side reactions of the acylated starting material may occur.
20 If the treatment with methanol according to the subject process is performed at a temperature between 5 C and 35 C, then the treatment period varies between 30 min and 3 h. A temperature increase to appr. 50 C reduces the reaction time to 25 min to l,Sh.
25 In order to remove all methanol from the methanol-soluble fraction, the extract is dried at a normal pressure at temperatures between 70 C and 120 C.
In order to be sure of the reproducibility of the quantitative chemical composition of the methanol-extracted fraction, which constitutes the subject phospholipid 30 composition, it is recommended to produce the phospholipid composition at a mass ratio of acylated crude phosphatide to methanol between 1:3 and 1:5.
As was stated above, the subject phospholipid composition acquired in this manner, can be further processed as a solid preparation or preferably in a suitable solvent, in 35 particular propylene glycol. A mass ratio of the isolated methanol-soluble fraction (represented as the methanol-free subject phospholipid composition) to the solvent between 7:3 and 9:1 is selected.
As was declared previously in connection with the subject phospholipid composition, 40 this subject phospholipid composition is suitable as an admixture in the production of food products, luxury products, cosmetics or pharmaceutical products. The expression "luxury products" represents such products, which are fit for human consumption, like for instance chocolate, cake, biscuits, soft drinks and others, whereas the expression "cosmetics" represents such products, which may change the human exterior, in 45 particular skin care products, skin browning products, face packs, deodorants, balhin~
products, perfumes, eau de toilettes, lipsticks, eye-liners, or others.
',~''" . ' ` ` ~ ` ' ~'`' ~ ' ' , ' 211~773 It is most preferred, to use the previously described phospholipid composition as an emulsifier or dispersifier in cosmetic preparations, in food products, in luxury products or in pharmaceutical preparations. For that reason the subject invention also relates to foodstuffs, luxury products, cosmetics or pharmaceutical preparations, which contain s any of the embodiments of the subject phospholipid composition.
If the subject phospholipid composition is being used for the production of cosmetic or pharmaceutical preparations, then these preparations may have a fluid, a halr-solid or a solid form.
A fluid cosmetic or pharmaceutical preparation may have the forrn of drops, tinctures or sprays, which may contain, in addition to the subject phospholipid composition, further active ingredients, which furlher ingredients may be dissolved, suspended, emulsified or dispersed.
A half-solid cosmetic or pharmaceutical preparation may have the form of a gel, an ointment, a cream or a foam; solid preparations may have the form of powders, granulates, pellets or micro capsules.
20 If the previously described phospholipid composition is prepared as a pharmaceutical and/or cosmetic preparation in a fluid dosage form, then it is recommendable to use solvents, which do not irritate the skin when being applied topically. Such solvents are water, alcohols with one hydroxy group, like ethanol, ispropano1 and n-propanol,alcohols with more than one hydroxy group, in particular glycerol and/or propanediol, 25 polyglycols, in particular poly ethylene glycol, poly propylene glycol and/or Miglyol, glycerinformal, dimethyl isosorbite, natural and synthetic oils and/or esters.
For the preparation of the half solid preparations like gels, ointments, creams and foams, besides the previously mentioned solvents, various groundmass materials may 30 be used, like bentonite, veegum, guar flour and/or cellulose derivatives, in particular methyl cellulose and/or carboxy methyl cellulose. Additional possible groundmassmaterials are polymers from vinyl alcohols, vinyl pyrrolidones, alginates, pectines, polyacrylates, solid and/or fluid polyethylene glycols, paraffins, fat alcohols, vaseline, waxes, fatty acids and/or esterified fatly esters.
To produce the solid preparations, like the before-mentioned powders, granulates, pellets or micro capsules, there is the possibility to use as an agglutinant for instance colloidal silicum dioxide, talcum, lactose, starch, sugar, cellulose derivatives, gelatine metal oxides and/or metal salts. The concentration of the inventive phospholipid40 composition in such solid pharmaceutical and/or cosmetic preparations depends on the intended use of these preparations.
A cosmetic and/or pharmaceutical preparation manufactured using the inventive phospholipid composition may contain further possible components which comprise 45 specific active ingredients, preservatives, stabilisers, surfactants, emulsifiers, penetration enhancers, spreading agents and/or propellants.
~ 2111773 Advantageous embodiments of the subject phospholipid composition as well as of tllc subject process are defined in the dependent claims.
The subject phospllolipid composition and the subject process are described below in 5 the form of examples.
Example 1.
500 g raw acetylated cnlde phosphatide, which was produced from soybean crude o lecithin by acetylation according to PARDUN ("Die Pflanzenlecithine", Verlag fur Chemische Industrie H.Ziolkowsky KG, Augsburg 1988), was under permanent stirring (stirring device: Stephan UC5) treated with 1500 g methanol at 30~ C for 2 h.
Subsequently the stirred product was left standing for one hour until separation of a sediment. The methanolic phase was decanted and brought to dryness in a rotations evaporator. The process resulted in 120 g of phospholipid composition.
The concentrations of phosphatidylcholine, N-acetylphosphatidylethanolamine and phosphatidylethanolamine in the phospho1ipid composition were determined quantitatively. The analysis resulted in the following values: 0 29,9 % by weight phosphatidylcholine, 27 % by weight N-acetylphosphatidylethanolamine, 0,1 % by weight phosphatidylethanolamine and 43 % by weight usual ingredients.
Qualitatively the usual ingredients can be defined as triglycerides, free fatty acids, sterols, tocopheroles, glycolipids, carbohydrates as well as other phospholipids.
120 g of the phospholipid composition were dissolved in 24 g propylene glycol and the 30 solution produced in this way was called solution I.
Example 2.
500 g acetylated crude phosphatide, produced in the same manner as described in 35 Example 1, was treated in the same manner as described in example 1. In contrast to the method used in example 1, 2000 g of methanol was used for the isolation of the pbospho1ipid composition, the isolation being performed in two phases, 1000 g methanol being used in each phase. The temperature during the isolation procedure was 15 C to 20 C. The further conditions were the same as in example 1.
40 After the evaporation of methanol the yield of phospholipid composition was 150 g.
In the joint phospholipid composition the concentration of phosphatidylcholine, N-acetylphosphatidylethanolamine and phosphatidylethanolamine was determined quantitatively.
45 The further ingredients were estimated qualitatively.
The fraction isolated in the above described manner from the methanol extract, showed the following composition:
'~'t ~ . , " , , ~:, 2~ 1773 24~5 % by weight phosphatidylcholine, 22 % by weight N-acetylphosphatidylethanolamine, 0,5 % by weight phosphatidylethanolamine and 53 % by weight usual ingredients.
The qualitative composition of the usual ingredients was the same as in example I .
150 g of the isolated fraction were dissolved in 30 g propylene glycol, which solution o was then named solution Il.
Example 3.
The isolation of the phospholipid composition was performed as described in example 1. Differing from that example, 2500 g methanol were used at 20 C to 25 C.
The methanol-free extract amounted to 168 g. In this isolated extract the concentrations of phosphatidylcholine, N-acetylphosphatidylethanolamine and phosphatidylethanolamine were determined quantitatively.
20 The further present usual ingredients were estimated qualitatively. Again they were qualitatively the same as in example 1.
The isolated, methanol-soluble extract provided the following composition:
21 % by weight phosphatidylcholine, 20,5 % by weight N-acetylphosphatidylethanolamine 1,5 % by weight phosphatidylethanolamine and 57,0 % by weight usual ingredients.
30 The isolated extract (168 g) was dissolved in 34 g propylene glycol. ~ - This solution was named solution 111.
Experimental example A.
3s In order to investigate the emulsifying capability of the solutions 1, 11 and Ill produced according to the examples I to 3 in comparison with crude lecithin (solution V) and acylated crude lecithin (solution IV), the following experiment was performed:
A fat mixture consisting of the following ingredients was prepared:
69,9 % by weight bovine grease, 30,0 % by weight coconut oil (Cocopur, Fa. Rau) and 0,1 % by weight Sudan red ( Fa. Fluka).
4s The above ingredients were melted at 70 C on a water bath and stirred until the dye was distributed homogeneously in the fat mixture.
2~1773 25,7 g of the melted fat mixture was mixed to homogeneily with 110 g low fat milk powder ( spray dried type) and 1,76 g phospholipid solution ( optionally solution 1, solution 11, solution 111, solution IV or solution V). These fat/milk/phospholipid mixtures were mixed with 1 I water (temperature 50 C, 10-15 dH) in a Krups mixer 5 according to the following schedule:
I minute step I
1 minute step 11 2 minut,es step 111.
This procedure led to the formation of an emulsion, which was poured into a calibrated cylinder pre-warmed at 50 C, whereby at the time of pouring the fluid was a homogeneous emulsion.
15 The height of the red-coloured separated fat layer was measured after 30 minutes and indicated in mm. The volume of the cylinder was I 1, all cylinders had identicaldimensions.
After 30 minutes the following thickness of the fat-phases was noted:
table 1.
Fat-layer thickness after a period of 30 minutes.
2S emulsifier thickness (mm) solution 1 3 (according to example 1) solution 11 4 30 (according to example 2) solution 111 7 (according to example 3) solution IV (*) 14 solution V (**) 21 3 s (*) and (**) comparative emulsifiers.
(*) 12 g acetylated crude lecithin (starting product in the examples 1-3), dissolved in 2,4 g propylene glycol ~; 40 (**) 12 g crude lecithin from soybean, dissolved in 2,4 g propylene glycol.
The values from table 1 illustrate without any doubt, that the solutions IV and V
constitute emulsifiers of substantially worse properties than the solutions I to 111.
i ......... : ,- , . ;-:
,~ - : . .. ,. . , .
r; ' : '' ~ : ' 21~77~
Experimcntal example B.
In order to prove, that the phospholipid compositions produced according to the 5 examples I to 3 possess excellent properties as emulsifying or dispersing agent, different flavours, scents, and light protective filters were emulsified or dis~ersed using the previously described solutions I to V.
The following,basis composition was used: 0 5 g of the product to be emulsified or dispersed and 4 g of one of the solutions I to V.
The previously mentioned ingredients were added together under stirring.
s Subsequently the mixed components were homogenised in a rapidly turning mixture (Waring Blender) with 100 g demineralised water for 7 min.
The particle size in the dispersions resp. the emulsions was determined by the "Laser Light Scattering" principle (Coulter N4SD ).
The stability of the prepared dispersions resp. emulsions was judged visually, whereby the next table 2 indicates the stability periods of the preparations, or the time when the investigation was broken off.
25 table 2.
emulsified or dispersed emulsifier particle stability product siæ (nm) perfume concentrate 1 solution lV 193 separation after 3 (producer 1) days perfume concentrate 1 solution 111 113 stable after 27 days;
(producer 1) investigation discontinued perfume concentrate 2 solution IV 188 separation after 4 -(producer2) days perfume concentrate 2 solution 1 127 stable after 27 days;
(producer 2) investigation discontinued light filter (Parsol MCX) solution IV 323 separation after 3 days 12 21117 1 ~
light filter (Parsol MCX) solution 111 294 stable after 27 days;
investigation discontinued light filter (Eusolex solution IV 360 separation after 3 4360) days light filter (Eusolex solution Ill 294 stable after 27 days;
4360) afler 29 days visible separation light filter /(Eusolex solution 11 272 stable after 45 days;
4360) investigation discontinued Experimental example C.
5 A sun protection gel C was prepared according to the following composition:
1. octyl methoxycinnamate 2,5%
2. benzophenone-3 0,5%
3. thistle oil 10,0%
lo 4. phospho1ipid composition according 6,0%
to example 1 5. water, dem. 79,0%
6. Hostacerin PN 73 1,0%
The content in N-acylphosphatidylethanolamine in the subject phospholipid composition varies between ~1 % by weight and 40 % by weight, preferably betweeno 24 % by weight and 28 % by weight .
In order to prevent the previously described unwanted reactions between phosphatidylethanolamine and any further ingredient, a further particularly suitable embodiment of the phospholipid composition provides a composition with a s phosphatidylethanolamine content between 0,01 % and 1,5 % by weight . In particular when the phosphatidylethanolamine content is below I % by weight, relative to the phospholipid composition, then said unwanted reactions, which may lead to changes in smell and/or taste andtor which may lead to unwanted colour changes, are prevented.
20 Another embodiment of the subject composition provides, that the subject phospholipid composition comprises at least 30 % by weight negatively charged phospholipids, in particular N-acylphosphatidylethanolamine in the amount as stated before, phosphatidic acid at between appr. I % by weight and 3 % by weight, phosphatidylinositol at between appr. 2 % by weight and appr. 6 % by weight as well 25 as further negatively charged phospholipids, preferably salts of phosphatidylglycerol or its corresponding derivatives.
Due to its before-mentioned relatively high content in negatively charged phospholipids, such an embodiment is very effective to stabilise liposomes, produced 30 from phospholipid fractions, which contain a large concentration in phosphatidylcholine, in particular a concentration of at least 80% by weight andpreferably 90 % by weight .
A particularly suited and preferably used phospholipid composition according to the 35 invention comprises 25 %byweight - 30 %byweight phosphatidylcholine, 24 % by weight - 28 % by weight N-acylphosphatidylethanolamine, 0.01 % by weight - 1.5 % by weight phosphatidylethanolamine and 40.5 % by weight - 50.99 % by weight other ingredients.
The other ingredients of tbe above list may constitute the previously mentioned 40 ingredients, in particular triglycerides, free fatty acids, sterols, tocopheroles, glycolipids, carbohydrates or other phospholipids like for instance phosphatidic acid, Iysophosphatidylethanolamine, phosphatidylglycerol and/or their derivatives. Thepreviously mentioned embodiment of the subject phospholipid composition providesexcellent dispersing and emulsifying properties for a number of active ingredients or 21~1773 ingredients, making it a very appropriate product to be used in the production of foodstuffs, luxury products, cosmetics and/or pharmaceuticals. Furthermore, thisembodiment provides all advantages even in more pronounced form, as have been described before for the subject phospholipid composition.
In the previous text there was only spoken generally of N-acyl-phosphatidylethanolamine. Preferred products from this class of products are N-oleoylphosphatidylethanolamine, N-palmitoylphosphatidylethanolamine, N-stearylphosph?tidylethanolamine, N-miristoylphosphatidylethanolamine and/or N-o acetylphosphatidylethanolamine alone or as a mixture. Particularly preferred is anembodiment, which contains N-acylphosphatidylethanolamine consisting to at least 90 % by weight of N-acetylphosphatidylethanolamine. This specific embodiment is particularly suitable for the use in pharmaceutical and/or cosmetic preparations for topical use, since in particular N-acetylphosphatidylethanolamine is highly efficacious s in the prevention of skin irritations and eye irritations and furthermore possesses a therapeutic quality towards skin inflammations and/or skin damage. This phenomenon has been described extensively in the German patent applications P 42 42 959.5 and P
42 42 960.9.
20 All concentrations which have been cited in the present specification in connection with the inventive phospholipid composition especially for phosphatidylcholine, N-acylphosphatidylethano1amine and phosphatidylethanolamine were relative to a solid, undiluted phospho1ipid composition. This would mean the solid phospholipid composition to be used as such. For special cases it is to be recommended, in view of a 25 better handling, to use liquid formulations of the phospholipid composition, preferably so1utions of the subject phospholipid composition. Different solvents may be used depending on the specific chemical structure of the phospholipid compositions, so for instance Cl-C4-alcohols, mono-or diglycerides and/or poly-alcohols, so1utions inpropylene glycol being preferred. To prepare such solutions of the subject 30 phospholipid composition, 70 % by weight to 90 % by weight of the previously described subject phospholipid composition, comprising at least 20 % by weight phosphatidylcholine, at least 20 % by weight N-acylphosphatidylethanolamine and less than 3 % by weight phosphatidylethanolamine are dissolved in 30 % by weightto 10% by weight of propylene glycol.
The subject invention further relates to a process for the production of the previously described phospholipid composition.
The subject process for the production of the previously described phospholipid 40 composition utilises as starting material an acylated crude phosphatide, treats the crude phosphatide with methanol and isolates the methanol-soluble fraction.
The subject method distinguishes itself by the major advantage, that it is simple to perform and with a relatively simple apparatus. Use of the inventive method for the 45 manufacturing of the previously described inventive phospholipid composition results in short production times and as a consequence against a low cost price, the final phospholipid composition containing at least 20 % by weight N-acyl-phosphatidylethanolamine and less than 3 % by weight phosphatidylethanolamine, as 6 2~il773 .
well as the usual ingredients, like free fatty acids, sterols, tocopheroles, glycolipi<ls, carbohydrates, water, other phospholipids, in particular lysophosphati(lylcholille, Iysophosphatidylethanolamine, phosphatidic acid and/or phosphatidylglycerol.
5 A preferred starting mnterial for the subject invention is the lype of acylated crude phosphatide, which is obtained by acylation of crude soybean lecithin accordin~ to known methods, for instance described by PARDUN ( Pardun, Die Pflanzenlecithine,Verlag fur chemische Industrie, H.Ziolkowsky KG, Augsburg, 1988).
o In order to prevent any unwanted change in the used acylated crude phosphatideduring the treatment with the methanol and in particular to warrant, that the fraction isolated with methanol from the crude lecithin provides the chemical structure which was described above for the subject phospholipid composition, the treatment is preferably performed at room temperature, at a temperature range between 5 C and 5 35 C, in particular between 10 C and lS C. It is evident, that a higher temperature range may be selected, for instance between 35 C and 60 C, but the risk at such increased temperatures is connected with the danger, that unwanted side reactions of the acylated starting material may occur.
20 If the treatment with methanol according to the subject process is performed at a temperature between 5 C and 35 C, then the treatment period varies between 30 min and 3 h. A temperature increase to appr. 50 C reduces the reaction time to 25 min to l,Sh.
25 In order to remove all methanol from the methanol-soluble fraction, the extract is dried at a normal pressure at temperatures between 70 C and 120 C.
In order to be sure of the reproducibility of the quantitative chemical composition of the methanol-extracted fraction, which constitutes the subject phospholipid 30 composition, it is recommended to produce the phospholipid composition at a mass ratio of acylated crude phosphatide to methanol between 1:3 and 1:5.
As was stated above, the subject phospholipid composition acquired in this manner, can be further processed as a solid preparation or preferably in a suitable solvent, in 35 particular propylene glycol. A mass ratio of the isolated methanol-soluble fraction (represented as the methanol-free subject phospholipid composition) to the solvent between 7:3 and 9:1 is selected.
As was declared previously in connection with the subject phospholipid composition, 40 this subject phospholipid composition is suitable as an admixture in the production of food products, luxury products, cosmetics or pharmaceutical products. The expression "luxury products" represents such products, which are fit for human consumption, like for instance chocolate, cake, biscuits, soft drinks and others, whereas the expression "cosmetics" represents such products, which may change the human exterior, in 45 particular skin care products, skin browning products, face packs, deodorants, balhin~
products, perfumes, eau de toilettes, lipsticks, eye-liners, or others.
',~''" . ' ` ` ~ ` ' ~'`' ~ ' ' , ' 211~773 It is most preferred, to use the previously described phospholipid composition as an emulsifier or dispersifier in cosmetic preparations, in food products, in luxury products or in pharmaceutical preparations. For that reason the subject invention also relates to foodstuffs, luxury products, cosmetics or pharmaceutical preparations, which contain s any of the embodiments of the subject phospholipid composition.
If the subject phospholipid composition is being used for the production of cosmetic or pharmaceutical preparations, then these preparations may have a fluid, a halr-solid or a solid form.
A fluid cosmetic or pharmaceutical preparation may have the forrn of drops, tinctures or sprays, which may contain, in addition to the subject phospholipid composition, further active ingredients, which furlher ingredients may be dissolved, suspended, emulsified or dispersed.
A half-solid cosmetic or pharmaceutical preparation may have the form of a gel, an ointment, a cream or a foam; solid preparations may have the form of powders, granulates, pellets or micro capsules.
20 If the previously described phospholipid composition is prepared as a pharmaceutical and/or cosmetic preparation in a fluid dosage form, then it is recommendable to use solvents, which do not irritate the skin when being applied topically. Such solvents are water, alcohols with one hydroxy group, like ethanol, ispropano1 and n-propanol,alcohols with more than one hydroxy group, in particular glycerol and/or propanediol, 25 polyglycols, in particular poly ethylene glycol, poly propylene glycol and/or Miglyol, glycerinformal, dimethyl isosorbite, natural and synthetic oils and/or esters.
For the preparation of the half solid preparations like gels, ointments, creams and foams, besides the previously mentioned solvents, various groundmass materials may 30 be used, like bentonite, veegum, guar flour and/or cellulose derivatives, in particular methyl cellulose and/or carboxy methyl cellulose. Additional possible groundmassmaterials are polymers from vinyl alcohols, vinyl pyrrolidones, alginates, pectines, polyacrylates, solid and/or fluid polyethylene glycols, paraffins, fat alcohols, vaseline, waxes, fatty acids and/or esterified fatly esters.
To produce the solid preparations, like the before-mentioned powders, granulates, pellets or micro capsules, there is the possibility to use as an agglutinant for instance colloidal silicum dioxide, talcum, lactose, starch, sugar, cellulose derivatives, gelatine metal oxides and/or metal salts. The concentration of the inventive phospholipid40 composition in such solid pharmaceutical and/or cosmetic preparations depends on the intended use of these preparations.
A cosmetic and/or pharmaceutical preparation manufactured using the inventive phospholipid composition may contain further possible components which comprise 45 specific active ingredients, preservatives, stabilisers, surfactants, emulsifiers, penetration enhancers, spreading agents and/or propellants.
~ 2111773 Advantageous embodiments of the subject phospholipid composition as well as of tllc subject process are defined in the dependent claims.
The subject phospllolipid composition and the subject process are described below in 5 the form of examples.
Example 1.
500 g raw acetylated cnlde phosphatide, which was produced from soybean crude o lecithin by acetylation according to PARDUN ("Die Pflanzenlecithine", Verlag fur Chemische Industrie H.Ziolkowsky KG, Augsburg 1988), was under permanent stirring (stirring device: Stephan UC5) treated with 1500 g methanol at 30~ C for 2 h.
Subsequently the stirred product was left standing for one hour until separation of a sediment. The methanolic phase was decanted and brought to dryness in a rotations evaporator. The process resulted in 120 g of phospholipid composition.
The concentrations of phosphatidylcholine, N-acetylphosphatidylethanolamine and phosphatidylethanolamine in the phospho1ipid composition were determined quantitatively. The analysis resulted in the following values: 0 29,9 % by weight phosphatidylcholine, 27 % by weight N-acetylphosphatidylethanolamine, 0,1 % by weight phosphatidylethanolamine and 43 % by weight usual ingredients.
Qualitatively the usual ingredients can be defined as triglycerides, free fatty acids, sterols, tocopheroles, glycolipids, carbohydrates as well as other phospholipids.
120 g of the phospholipid composition were dissolved in 24 g propylene glycol and the 30 solution produced in this way was called solution I.
Example 2.
500 g acetylated crude phosphatide, produced in the same manner as described in 35 Example 1, was treated in the same manner as described in example 1. In contrast to the method used in example 1, 2000 g of methanol was used for the isolation of the pbospho1ipid composition, the isolation being performed in two phases, 1000 g methanol being used in each phase. The temperature during the isolation procedure was 15 C to 20 C. The further conditions were the same as in example 1.
40 After the evaporation of methanol the yield of phospholipid composition was 150 g.
In the joint phospholipid composition the concentration of phosphatidylcholine, N-acetylphosphatidylethanolamine and phosphatidylethanolamine was determined quantitatively.
45 The further ingredients were estimated qualitatively.
The fraction isolated in the above described manner from the methanol extract, showed the following composition:
'~'t ~ . , " , , ~:, 2~ 1773 24~5 % by weight phosphatidylcholine, 22 % by weight N-acetylphosphatidylethanolamine, 0,5 % by weight phosphatidylethanolamine and 53 % by weight usual ingredients.
The qualitative composition of the usual ingredients was the same as in example I .
150 g of the isolated fraction were dissolved in 30 g propylene glycol, which solution o was then named solution Il.
Example 3.
The isolation of the phospholipid composition was performed as described in example 1. Differing from that example, 2500 g methanol were used at 20 C to 25 C.
The methanol-free extract amounted to 168 g. In this isolated extract the concentrations of phosphatidylcholine, N-acetylphosphatidylethanolamine and phosphatidylethanolamine were determined quantitatively.
20 The further present usual ingredients were estimated qualitatively. Again they were qualitatively the same as in example 1.
The isolated, methanol-soluble extract provided the following composition:
21 % by weight phosphatidylcholine, 20,5 % by weight N-acetylphosphatidylethanolamine 1,5 % by weight phosphatidylethanolamine and 57,0 % by weight usual ingredients.
30 The isolated extract (168 g) was dissolved in 34 g propylene glycol. ~ - This solution was named solution 111.
Experimental example A.
3s In order to investigate the emulsifying capability of the solutions 1, 11 and Ill produced according to the examples I to 3 in comparison with crude lecithin (solution V) and acylated crude lecithin (solution IV), the following experiment was performed:
A fat mixture consisting of the following ingredients was prepared:
69,9 % by weight bovine grease, 30,0 % by weight coconut oil (Cocopur, Fa. Rau) and 0,1 % by weight Sudan red ( Fa. Fluka).
4s The above ingredients were melted at 70 C on a water bath and stirred until the dye was distributed homogeneously in the fat mixture.
2~1773 25,7 g of the melted fat mixture was mixed to homogeneily with 110 g low fat milk powder ( spray dried type) and 1,76 g phospholipid solution ( optionally solution 1, solution 11, solution 111, solution IV or solution V). These fat/milk/phospholipid mixtures were mixed with 1 I water (temperature 50 C, 10-15 dH) in a Krups mixer 5 according to the following schedule:
I minute step I
1 minute step 11 2 minut,es step 111.
This procedure led to the formation of an emulsion, which was poured into a calibrated cylinder pre-warmed at 50 C, whereby at the time of pouring the fluid was a homogeneous emulsion.
15 The height of the red-coloured separated fat layer was measured after 30 minutes and indicated in mm. The volume of the cylinder was I 1, all cylinders had identicaldimensions.
After 30 minutes the following thickness of the fat-phases was noted:
table 1.
Fat-layer thickness after a period of 30 minutes.
2S emulsifier thickness (mm) solution 1 3 (according to example 1) solution 11 4 30 (according to example 2) solution 111 7 (according to example 3) solution IV (*) 14 solution V (**) 21 3 s (*) and (**) comparative emulsifiers.
(*) 12 g acetylated crude lecithin (starting product in the examples 1-3), dissolved in 2,4 g propylene glycol ~; 40 (**) 12 g crude lecithin from soybean, dissolved in 2,4 g propylene glycol.
The values from table 1 illustrate without any doubt, that the solutions IV and V
constitute emulsifiers of substantially worse properties than the solutions I to 111.
i ......... : ,- , . ;-:
,~ - : . .. ,. . , .
r; ' : '' ~ : ' 21~77~
Experimcntal example B.
In order to prove, that the phospholipid compositions produced according to the 5 examples I to 3 possess excellent properties as emulsifying or dispersing agent, different flavours, scents, and light protective filters were emulsified or dis~ersed using the previously described solutions I to V.
The following,basis composition was used: 0 5 g of the product to be emulsified or dispersed and 4 g of one of the solutions I to V.
The previously mentioned ingredients were added together under stirring.
s Subsequently the mixed components were homogenised in a rapidly turning mixture (Waring Blender) with 100 g demineralised water for 7 min.
The particle size in the dispersions resp. the emulsions was determined by the "Laser Light Scattering" principle (Coulter N4SD ).
The stability of the prepared dispersions resp. emulsions was judged visually, whereby the next table 2 indicates the stability periods of the preparations, or the time when the investigation was broken off.
25 table 2.
emulsified or dispersed emulsifier particle stability product siæ (nm) perfume concentrate 1 solution lV 193 separation after 3 (producer 1) days perfume concentrate 1 solution 111 113 stable after 27 days;
(producer 1) investigation discontinued perfume concentrate 2 solution IV 188 separation after 4 -(producer2) days perfume concentrate 2 solution 1 127 stable after 27 days;
(producer 2) investigation discontinued light filter (Parsol MCX) solution IV 323 separation after 3 days 12 21117 1 ~
light filter (Parsol MCX) solution 111 294 stable after 27 days;
investigation discontinued light filter (Eusolex solution IV 360 separation after 3 4360) days light filter (Eusolex solution Ill 294 stable after 27 days;
4360) afler 29 days visible separation light filter /(Eusolex solution 11 272 stable after 45 days;
4360) investigation discontinued Experimental example C.
5 A sun protection gel C was prepared according to the following composition:
1. octyl methoxycinnamate 2,5%
2. benzophenone-3 0,5%
3. thistle oil 10,0%
lo 4. phospho1ipid composition according 6,0%
to example 1 5. water, dem. 79,0%
6. Hostacerin PN 73 1,0%
7. Perfume concentrate 0,5%
8. phenonip 0,5%
To produce the sun protective gel, a clear solution was made under heating from the ingredients 1 to 3. Ingredient 4 was added to the clear solution at the same temperature. Subsequently the water (ingredient 5) was warmed to the respective 20 temper:ature and the mixture of the ingredients I to 4 was added under stirring to this water. The temperature during the dispersing procedure was 60 C to 70 C. A
~- dispersion was stirred for a time sufficient for particles of appr. 250 nm to be formed.
The dispersion was cooled to room temperature and mixed with Hostacerin (ingredient 6), the perfume concentrate (ingredient 7) and the preservative (ingredient 8), thereby 25 forming the sun protective gel C.
Experimentaî example D. ~ -A sun protective gel D was formulated from the following components, according to 30 the same method as the one used for the production of sun protective gel C.
5.jj ~
The sun protective gel D contained the following ingredients:
I. octyl methoxycinnamate 4,0%
s 2. benzophenone-3 1,0%
3. Miglyol 812 10,0%
4. phospholipid compositionaccording 5,0%
to example 2 S. water dem. 77,3%
o 6. xanthan 1,7%
7. phenonip 0,5%
8. perfume concentrate 0,5%.
Experimental example E.
A pre-shave lotion E was produced, which comprised the following ingredients:
1. phospholipid composition according 0,5%
to example 3 2. alpha-tocopherol 0,5%
3. perfumeoil 0,25%
4. Carbopol 980 0,75%
5. NaOH, 10% q.s.
6. ethanot 15%
7. water, dem. 82,0%
8. phenonip 1,0%
- The ingredients 1 to 3 were pre-mixed and mixed with a third of the total amount of water and stirred until a dispersion was present, which contained particles with a size 30 of appr. 200 nm. This dispersion was processed into ingredient 4. After completion of the swelling the remaining water was admixed and the pH value of the lotion was adjusted to 6,8 with ingredient 5. Finally ingredients 6 and 8 were admixed.
Experimental example F.
A sunprotective lotion F was produced from the following ingredients: ~ :
1. Crodamol DOA 8,0%
2. Cithrol GMS/AS 6,0%
3. Crodamol PMP 5,0%
4. BaseCB3929 5,0%
5. Antaron V-220 2,0%
6. Emulgin B 2 1,2%
7. Emutgin B l 0,8%
8. Carbopol 980 0,1%
To produce the sun protective gel, a clear solution was made under heating from the ingredients 1 to 3. Ingredient 4 was added to the clear solution at the same temperature. Subsequently the water (ingredient 5) was warmed to the respective 20 temper:ature and the mixture of the ingredients I to 4 was added under stirring to this water. The temperature during the dispersing procedure was 60 C to 70 C. A
~- dispersion was stirred for a time sufficient for particles of appr. 250 nm to be formed.
The dispersion was cooled to room temperature and mixed with Hostacerin (ingredient 6), the perfume concentrate (ingredient 7) and the preservative (ingredient 8), thereby 25 forming the sun protective gel C.
Experimentaî example D. ~ -A sun protective gel D was formulated from the following components, according to 30 the same method as the one used for the production of sun protective gel C.
5.jj ~
The sun protective gel D contained the following ingredients:
I. octyl methoxycinnamate 4,0%
s 2. benzophenone-3 1,0%
3. Miglyol 812 10,0%
4. phospholipid compositionaccording 5,0%
to example 2 S. water dem. 77,3%
o 6. xanthan 1,7%
7. phenonip 0,5%
8. perfume concentrate 0,5%.
Experimental example E.
A pre-shave lotion E was produced, which comprised the following ingredients:
1. phospholipid composition according 0,5%
to example 3 2. alpha-tocopherol 0,5%
3. perfumeoil 0,25%
4. Carbopol 980 0,75%
5. NaOH, 10% q.s.
6. ethanot 15%
7. water, dem. 82,0%
8. phenonip 1,0%
- The ingredients 1 to 3 were pre-mixed and mixed with a third of the total amount of water and stirred until a dispersion was present, which contained particles with a size 30 of appr. 200 nm. This dispersion was processed into ingredient 4. After completion of the swelling the remaining water was admixed and the pH value of the lotion was adjusted to 6,8 with ingredient 5. Finally ingredients 6 and 8 were admixed.
Experimental example F.
A sunprotective lotion F was produced from the following ingredients: ~ :
1. Crodamol DOA 8,0%
2. Cithrol GMS/AS 6,0%
3. Crodamol PMP 5,0%
4. BaseCB3929 5,0%
5. Antaron V-220 2,0%
6. Emulgin B 2 1,2%
7. Emutgin B l 0,8%
8. Carbopol 980 0,1%
9. water, dem. 4,9%
10. phospholipid composition 6,0%
according to example 2 Il. octyl methoxycinnamate 6,0% 211177 3 12. propylene glycol 2,0%
13. Aloe vera gel 2/912800 2,0%
14. water, dem. 47,0%
15. Panthenol 50 P 2,0%
16. perfume oil Lafetto 0,3%
100.034 17. EuxylK400 0,1%
18. triethanolamine lO% 1,6%
The ingredients 10, 11 and 14 were dispersed until the formation of particles with a mean size of appr. 200 nm. To this dispersion the ingredients 12 and 13, as well as the gel consisting of ingredients 8 and 9, were admixed. This whole phase was then added to the combination of the ingredients 1 to 7 which had been melted and homogenised.
s The joint phases were cooled to a temperature of about 35 C. The generated product was mixed with the ingredients 15, 16, 17 and 18 and cooled to room temperature under stirring.
20 Experimental example G.
A caring cream G was produced from the following ingredients:
1. Emulgin B 1 2,0%
2. Syncrowax BB 4 2,0%
3. Crodawax GP 200 3,0%
4. Cithrol GMS/AS 4,0%
5. Dow DC 345 5.0%
6. Promyristyl PM 3 10,0%
7. Miglyol 812 10,0%
8. phospholipidcomposition 4,0%
according to example 2 9. water, dem. 57,7%
10. propylene glycol 2,0%
I E perfume oil 0,2~/o 12. EuxylK400 0,1%.
For the production of the caring cream G, the ingredients 8 to 10 were dispersed at 70 C. To this dispersion were admixed at 70 C the homogenised phase, which comprised 40 the ingredients 1 to 7 and had been prepared by the melting of the products I to 7 at 70 C and mixing them with each other. The mixture was cooled under stirring to about 40 C and mixed at this temperature with the ingredients 11 and 12.
Subsequently the cream was cooled to room temperature under stirring.
In order to investigate, if the products produced accordin~ to the experimental examples C to G provoked any skin irritations, an investigation hl volunteers was performed.
5 For this purpose for each of the experimental example preparations a selection of 50 vohmteers was made, who, according to their own judgement, showed a high sensitivity to cosmetic preparations.
In each volunteer 0,5 g of every preparation were applied on a localised site at the o lower arm (area appr. 4 cm2) 5 times with intervals of 2 h each time .
Before the following application a visual control was performed, if any skin irritation had occurred. The results of this investigation are depicted in the following table 3.
15 table 3.
Investigation of skin irritation in 50 volunteers per preparation Preparation according to number of volunteers with skin irritation after application experimental example 1 st appl. 2nd appl. 3rd appl. 4th appl. 5th appl.
E O O O O
G O O O O O
-Furthermore, all of the products which had been investigated in volunteers according to the above description were investigated in a stability test. In this investigation the preparations were kept at a relative humidity of 65% and a temperature of 40 C for a period of 30 days.
0 During the storage period and thereafter, the smell and the consistency were checked, without any changes to be observed .
.
according to example 2 Il. octyl methoxycinnamate 6,0% 211177 3 12. propylene glycol 2,0%
13. Aloe vera gel 2/912800 2,0%
14. water, dem. 47,0%
15. Panthenol 50 P 2,0%
16. perfume oil Lafetto 0,3%
100.034 17. EuxylK400 0,1%
18. triethanolamine lO% 1,6%
The ingredients 10, 11 and 14 were dispersed until the formation of particles with a mean size of appr. 200 nm. To this dispersion the ingredients 12 and 13, as well as the gel consisting of ingredients 8 and 9, were admixed. This whole phase was then added to the combination of the ingredients 1 to 7 which had been melted and homogenised.
s The joint phases were cooled to a temperature of about 35 C. The generated product was mixed with the ingredients 15, 16, 17 and 18 and cooled to room temperature under stirring.
20 Experimental example G.
A caring cream G was produced from the following ingredients:
1. Emulgin B 1 2,0%
2. Syncrowax BB 4 2,0%
3. Crodawax GP 200 3,0%
4. Cithrol GMS/AS 4,0%
5. Dow DC 345 5.0%
6. Promyristyl PM 3 10,0%
7. Miglyol 812 10,0%
8. phospholipidcomposition 4,0%
according to example 2 9. water, dem. 57,7%
10. propylene glycol 2,0%
I E perfume oil 0,2~/o 12. EuxylK400 0,1%.
For the production of the caring cream G, the ingredients 8 to 10 were dispersed at 70 C. To this dispersion were admixed at 70 C the homogenised phase, which comprised 40 the ingredients 1 to 7 and had been prepared by the melting of the products I to 7 at 70 C and mixing them with each other. The mixture was cooled under stirring to about 40 C and mixed at this temperature with the ingredients 11 and 12.
Subsequently the cream was cooled to room temperature under stirring.
In order to investigate, if the products produced accordin~ to the experimental examples C to G provoked any skin irritations, an investigation hl volunteers was performed.
5 For this purpose for each of the experimental example preparations a selection of 50 vohmteers was made, who, according to their own judgement, showed a high sensitivity to cosmetic preparations.
In each volunteer 0,5 g of every preparation were applied on a localised site at the o lower arm (area appr. 4 cm2) 5 times with intervals of 2 h each time .
Before the following application a visual control was performed, if any skin irritation had occurred. The results of this investigation are depicted in the following table 3.
15 table 3.
Investigation of skin irritation in 50 volunteers per preparation Preparation according to number of volunteers with skin irritation after application experimental example 1 st appl. 2nd appl. 3rd appl. 4th appl. 5th appl.
E O O O O
G O O O O O
-Furthermore, all of the products which had been investigated in volunteers according to the above description were investigated in a stability test. In this investigation the preparations were kept at a relative humidity of 65% and a temperature of 40 C for a period of 30 days.
0 During the storage period and thereafter, the smell and the consistency were checked, without any changes to be observed .
.
Claims (25)
1. A phospholipid composition with a content of at least 20 % by weight phosphatidylcholine, wherein said composition comprises at least 20 % by weight N-acylphosphatidylethanolamine as well as less than 3 % by weight phosphatidylethanolamine besides the usual ingredients.
2. The composition according to claim 1, wherein the composition comprises between 22 % by weight and 40 % by weight, in particular between 25 % by weight and 30 %by weight phosphatidylcholine.
3. The composition according to one of the preceding claims, wherein the composition comprises between 21 % by weight and 40 % by weight, in particular between 24 %
by weight and 28 % by weight N-acylphosphatidylethanolamine.
by weight and 28 % by weight N-acylphosphatidylethanolamine.
4. The composition according to one of the preceding claims, wherein the composition comprises between 0,01 % by weight and 1,5 % by weight phoshatidylethanolamine.
5. The composition according to one of the preceding claims, wherein the composition comprises at least 30 % negatively charged phospholipids.
6. The composition according to one of the preceding claims, wherein the composition comprises % by weight - 30 % by weight phosphatidylcholine 24 % by weight - 28 % by weight N-acylphosphatidylethanolamine 0.01 % by weight - 1.5 % by weight phosphatidylethanolamine 40.5 % by weight - 50.99 % by weight other ingredients
7. The composition according to one of the preceding claims wherein said N-acylphosphatidylethanolamine comprises N-oleoylphosphatidylethanolamine, N-palmitoylphosphatidylcholine, N-stearylphosphatidylethanolamine, N-miristoylphosphatidylethanolamine anWor N-acetylphosphatidylethanolamine, alone or as a mixture.
8. The composition, according to claim 7, wherein said N-acylphosphatidylethanolamine comprises at least 90 % by weight N-acetylphosphatidylethanolamine.
9. The composition, according to one of the preceding claims, wherein the composition is prepared in a solvent, leading to a fluid preparation.
10. The composition according to claim 9, wherein said fluid preparation comprises 70 % by weight to 90 % by weight of the solid phospholipid composition and as a solvent 30 % by weight to 10 % by weight propylene glycol.
11. A process for the preparation of the phospholipid composition according to one of the preceding claims, wherein the starting material is acylated crude lecithin and said crude lecithin is treated with methanol and the methanol-soluble fraction is isolated.
12. The process according to claim 11, wherein the treatment is performed at a temperature between 5° C and 35° C.
13. The process according to claims 11 or 12, wherein said treatment with methanol is performed for a period of between 30 min and 3 hours.
14. The process according to one of the claims 11 to 1 3, wherein the methanol-soluble fraction is dried at a temperature between 70° C and 120° C to isolate the phospholipid composition.
15. The process according to one the claims 11 to 14, wherein the mass ratio of acylated crude phosphatide to methanol varies between 1:3 and 1:5.
16. The process according to one of the claims 11 to 15, wherein the isolated methanol-soluble fraction, after the removal of the methanol, is dissolved in a suitable solvent, in particular propylene glycol.
17. Use of the phospholipid composition according to one of the claims 1 to 10 as ingredient for the production of foodstuffs, luxury products, cosmetics and/or pharmaceuticals.
18. The use of the phospholipid composition according to one of the claims 1 to 10 as emulsifier, dispersifier, active ingredient and/or preservative agent in cosmetic compositions.
19. The use of the phospholipid composition according to one of the claims 1 to 10 as emulsifier, dispersifier and/or preservative agent in foodstuffs or luxury products.
20. The use of the phospholipid composition according to one of the claims 1 to 10 as emulsifier, dispersifier, active ingredient and/or preservative agent in pharmaceutical preparations.
21. The use of the phospholipid composition according to one of the claims 1 to 10 as emulsifier, dispersifier and/or preservative agent in perfume or perfume starting material.
22. Foodstuff, wherein said foodstuff comprises a phospholipid composition as emulsifier, dispersifier and/or preservative, which phospholipid composition comprises at least 20 % by weight phosphatidylcholine, at least 20 % by weight N-acylphosphatidylethanolamine and less than 3 % by weight phosphatidylethanolamine besides the usual excipients.
23. Luxury product, wherein said luxury product comprises a phospholipid composition as emulsifier, dispersifier and, or preservative agent, which phospholipid composition comprises at least 20 % by weight phosphatidylcholine, at least 20 % by weight N-acylphosphatidylethanolamine and than 3 % by weight phosphatidyiethanolamine besides the usual excipients.
24. Cosmetic preparation, wherein said cosmetic preparation comprises a phospholipid composition as emulsifier, dispersifier, preservative agent and/or active ingredient, which phospholipid composition comprises at least 20 % by weight phosphatidylcholine, at least 20 % by weight N-acylphosphatidylethanolamine and less than 3 % by weight phosphatidylethanolamine besides the usual excipients.
25. Pharmaceutical preparation, wherein said pharmaceutical product comprises a phospholipid composition as emulsifier, dispersifier, active ingredient and/or preservative agent, which phospholipid composition comprises at least 20 % by weight phosphatidylcholine, at least 20 % by weight N-acylphosphatidylethanolamine and less than 3 % by weight phosphatidylethanolamine besides the usual excipients.
Applications Claiming Priority (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP4242959.5 | 1992-12-18 | ||
| DE4242959 | 1992-12-18 | ||
| DEP4242960.9 | 1992-12-18 | ||
| DE4242960 | 1992-12-18 | ||
| DEP4302074.7 | 1993-01-26 | ||
| DE4302074 | 1993-01-26 | ||
| DEP4305554.0 | 1993-02-24 | ||
| DE4305554A DE4305554C2 (en) | 1992-12-18 | 1993-02-24 | Phospholipidic composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2111773A1 true CA2111773A1 (en) | 1994-06-19 |
Family
ID=27435660
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002111773A Abandoned CA2111773A1 (en) | 1992-12-18 | 1993-12-17 | Phospholipid composition |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP0604806A3 (en) |
| JP (1) | JPH06279467A (en) |
| CA (1) | CA2111773A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8361496B2 (en) | 2004-06-24 | 2013-01-29 | Idexx Laboratories Inc. | Phospholipid gel compositions for drug delivery and methods of treating conditions using same |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2776300B1 (en) * | 1998-03-23 | 2000-08-11 | Pernod Ricard | NEW LIMPID ANCOHOLIC CONTAINING POTENTIALLY ALCOHOLIC BEVERAGE AND DILUTED DISORDERED DILUTION |
| CA2432136A1 (en) * | 2000-12-28 | 2002-07-11 | Kiyoshi Ebihara | Pharmaceutical emulsion preparation |
| JP4634040B2 (en) * | 2002-02-12 | 2011-02-16 | ウンザー ディ ピストレージ エルヴィラ エ チ． エッセ．ア．エッセ． | Phospholipid mixture, phosphobioflavone complex, and composition containing the phosphorioflavone complex |
| ITMI20041280A1 (en) * | 2004-06-24 | 2004-09-24 | Hunza Di Pistolesi Elvira & C | DIETETIC AND COSMETIC PHARMACEUTICAL PREPARATION FOR THE TREATMENT OF CELLULITE ALOPECIA OBESITY AND SKIN AGING |
| CN104853614A (en) * | 2012-10-24 | 2015-08-19 | 卡吉尔公司 | Phospholipid-containing emulsifier composition |
| JP2018050521A (en) * | 2016-09-28 | 2018-04-05 | 株式会社Ｊ−オイルミルズ | Milk yield improving agent for mammals |
| CN114403224A (en) * | 2021-12-20 | 2022-04-29 | 蚌埠市和平乳业有限责任公司 | High-stability modified milk and preparation method thereof |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3125448A1 (en) * | 1981-06-27 | 1983-01-13 | A. Nattermann & Cie GmbH, 5000 Köln | "NEW ACARICID COMPOSITION, METHOD FOR THE PRODUCTION AND USE THEREOF" |
| DE3312166A1 (en) * | 1983-04-02 | 1984-10-11 | Hoechst Ag, 6230 Frankfurt | LIPOTENSIDE, METHOD FOR INSULATION AND THEIR USE |
| DE3616594C2 (en) * | 1986-05-16 | 1994-07-28 | Kampffmeyer Muehlen | Baking agent for bread dough |
| ES2076203T3 (en) * | 1988-12-22 | 1995-11-01 | Kanebo Ltd | COSMETIC COMPOSITION. |
-
1993
- 1993-12-10 EP EP93119922A patent/EP0604806A3/en not_active Withdrawn
- 1993-12-17 CA CA002111773A patent/CA2111773A1/en not_active Abandoned
- 1993-12-20 JP JP5345110A patent/JPH06279467A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8361496B2 (en) | 2004-06-24 | 2013-01-29 | Idexx Laboratories Inc. | Phospholipid gel compositions for drug delivery and methods of treating conditions using same |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0604806A3 (en) | 2000-07-19 |
| JPH06279467A (en) | 1994-10-04 |
| EP0604806A2 (en) | 1994-07-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |