WO2006087156A1 - Nanoemulsions comprising lipoaminoacids and monoglycerides, diglycerides and polyglycerides of fatty acids - Google Patents
Nanoemulsions comprising lipoaminoacids and monoglycerides, diglycerides and polyglycerides of fatty acids Download PDFInfo
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- WO2006087156A1 WO2006087156A1 PCT/EP2006/001277 EP2006001277W WO2006087156A1 WO 2006087156 A1 WO2006087156 A1 WO 2006087156A1 EP 2006001277 W EP2006001277 W EP 2006001277W WO 2006087156 A1 WO2006087156 A1 WO 2006087156A1
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- Prior art keywords
- nanoemulsions
- fatty acids
- lipoaminoacids
- monoglycerides
- diglycerides
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Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/04—Dispersions; Emulsions
- A61K8/06—Emulsions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/37—Esters of carboxylic acids
- A61K8/375—Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- 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
- A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
- A61K2800/21—Emulsions characterized by droplet sizes below 1 micron
-
- 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
- A61K2800/41—Particular ingredients further characterized by their size
- A61K2800/413—Nanosized, i.e. having sizes below 100 nm
-
- 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
- A61K9/10—Dispersions; Emulsions
- A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
- A61K9/1075—Microemulsions or submicron emulsions; Preconcentrates or solids thereof; Micelles, e.g. made of phospholipids or block copolymers
Definitions
- This invention relates to nanoemulsions containing lipoaminoacids and monoglycerides, diglycerides and polyglycerides of fatty acids as emulsifiers.
- Nanoemulsions are emulsions wherein the particle size of the internal phase is normally under 100 nm. This particle size is usually obtained by drastically reducing the interface tension of the system. According to Stokes' law, the sedimentation rate of the particles is directly proportional to twice the square of the particle diameter. Hence the smaller the particle size, the more stable the dispersion obtained.
- Nanoemulsions can be used as a vehicle for transparent or translucent active ingredients with a particularly attractive appearance. Nanoemulsions are advantageously used in numerous applications. However, nanoemulsions are a system with a very delicate balance wherein even the addition of a single non-compatible component can jeopardise the stability and coagulation of the particles. Another known problem of nanoemulsions is their inability to incorporate large amounts of oil.
- nanoemulsions have a relatively high content of emulsifiers such as fatty acids or ethoxylated or propoxylated fatty acids which, however, present problems of unsatisfactory skin tolerability and local toxicity.
- emulsifiers such as fatty acids or ethoxylated or propoxylated fatty acids which, however, present problems of unsatisfactory skin tolerability and local toxicity.
- the problem of skin irritability is particularly felt, because nanoemulsions represent the ideal cosmetic and pharmaceutical vehicle for cosmetic active constituents; they easily permeate the first cell layer of the epidermis, and then release the necessary active constituents.
- Nanoemulsions recently studied and developed as a vehicle for cosmetic, dermatological and pharmaceutical active ingredients are described, for example, in US 2004445159 Al and EP-Al-1160005.
- the nanoemulsions obtained so far contain synthetic surfactants deriving from ethylene or propylene oxide or phosphoric esters with a high surface energy which is advantageous in terms of stability but promotes penetration of the epidermis, leading to problems of skin intolerance, reddening and allergies due to ethylene and/or propylene oxide derivatives.
- phospholipids as emulsifiers has not yet proved wholly satisfactory as regards cosmetic emollient characteristics. It has now been discovered that stable, well-tolerated nanoemulsions can be obtained which are able to carry cosmetic or pharmaceutical active ingredients with a variety of chemico-physical characteristics by using at least one lipoaminoacid or a mixture thereof, associated with monoglycerides, diglycerides or polyglycerides of fatty acids, either individually or combined with one another.
- the nanoemulsions according to the invention can contain a high percentage of lipids, and do not contain emulsifiers deriving from ethylene or propylene oxide, phosphoric esters, sulphated derivatives, etc.. They present a high level of skin tolerability and have a particle size of between 50 and 500 nm, and preferably between 50 and 100 nm.
- Lipoaminoacids are obtained by reaction between fatty acids and at least one aminoacid or a mixture of aminoacids chosen from among glutamic acid, glycine, proline, arginine, valine, leucine, alanine, isoleucine, tryptophan, methionine, phenylalanine, serine, threonine, cysteine, tyrosine, asparagine, glutamine, aspartic acid, lysine, histidine, sarcosine, ornithine and desmosine.
- aminoacids chosen from among glutamic acid, glycine, proline, arginine, valine, leucine, alanine, isoleucine, tryptophan, methionine, phenylalanine, serine, threonine, cysteine, tyrosine, asparagine, glutamine, aspartic acid, lysine, histidine, sarcos
- lipoaminoacids can be obtained by reaction between fatty acids and carnitine, creatine or peptides such as carnosine, glutathione and their physiologically equivalent derivatives.
- the lipoaminoacids can be salified with alkaline metals, alkaline earths or amine bases, for example in the form of potassium, sodium, magnesium, triethanolamine or methylpropanolamine salts.
- the fatty acids are preferably chosen from among octanoic, decanoic, lauric, myristic, palmitic, oleic, stearic, linoleic, linolenic, erucic and behenic acid or mixtures thereof; alternatively, fatty acids obtained from coconut, palm, olive, sunflower, peanut, soya or sweet almond oil or other vegetable oils can be used.
- Lipoaminoacids are present in the nanoemulsions according to the invention in percentages of between 0.1 and 15% in weight of the total nanoemulsion, and preferably between 1 and 4%, while monoglycerides, diglycerides and polyglycerides of fatty acids are present in percentages of between 0.2 and 10% in weight of the total nanoemulsion, and preferably between 1 and 4%.
- Lipoaminoacids are already used in cosmetics because they easily permeate the first layer of the epidermis, where they release the aminoacid portion and fatty acids that promote the restructuring and defence of the skin.
- Glycerol and polyglycerol esters of fatty acids represent the "co-emulsifier"; they are all soluble in the oily phase of the nanoemulsion, have a low interface energy, and do not affect the natural state of aggregation of the lipids and hydrophilic cutaneous substances.
- the nanoemulsions according to the invention can contain a large amount of lipids.
- the nanoemulsions according to the invention are highly homogenous monophase systems, and have an appearance ranging from semitransparent to sheer with beige/blue highlights, typical of nanoemulsions.
- the nanoemulsion preparation methods described so far involve the use of high pressures and temperatures; as a result, they are not easily reproduced at industrial level, and are expensive.
- the nanoemulsions to which this invention relates can be obtained with conventional emulsifying methods but with the advantage of considerable energy saving, in terms of both the mechanical energy required by the emulsifying devices and as regards heat, as they can be produced by pre-heating only the fatty phase containing the lipoaminoacid and the monoglycerides, diglycerides and polyglycerides of fatty acids, with a low input of mechanical energy.
- the industrial manufacturing processes are therefore reproducible and economical.
- the nanoemulsion obtained with the lipoaminoacid is dermatologically compatible, safe in toxicological terms, and can easily carry active constituents such as vitamins, alpha hydroxy acids, aminoacids, medicinal plant extracts and other cosmetologically functional substances to the surface skin layers.
- the nanoemulsions thus obtained can be used in the cosmetic, dermopharmaceutical and pharmaceutical industries due to their increased biological activity and skin penetration ability, and the improvement in the normal natural barrier functions of the cutaneous hydrolipid film.
- nanoemulsions according to the invention have low viscosity; they can be used "as is” and delivered by nebuliser spray or viscosified with conventional gelling agents.
- the nanoemulsions according to the invention are also distinguished by their exceptional stability, even though they are free of viscosity at both high and low lipid concentrations.
- the nanoemulsion according to the invention can contain between 1 and 60% of fatty phase and between 40 and 99% of water, demonstrating the great versatility of the system.
- potassium lauroyl wheat amino acids 90 g is dissolved in a phase consisting of 80 g octyl palmitate, 30 g palm monoglycerides, 10 g jojoba oil and 5 g vitamin E.
- the mixture is heated to 60-70 0 C and the water is then added by degrees, taking care to ensure that the first part (approx. 20%) is well absorbed.
- a translucent lipogel is formed which, with the addition of the rest of the water, forms a nanoemulsion whose particles have a diameter of approx. 80 nm.
- Moisturising substances (20 g sodium lactate and 20 g sodium PCA), fragrance and preservative are added at the end.
- Heat shock means 3 cycles of 24 hours each at 4°C and 40 0 C alternately
- 60 g sodium lauroyl oat amino acids is dissolved in a phase consisting of 60 g caprylic/capric triglyceride, 20 g polyglyceryl isostearate, 1O g sweet almond oil and 2 g vitamin A palmitate.
- the mixture is heated to 60-70 0 C and the water is then added by degrees, taking care to ensure that the first part
- a translucent lipogel is formed which, with the addition of the rest of the water, forms a nanoemulsion whose particles have a diameter of approx. 80 nm.
- Moisturising substances are added at the end.
- Heat shock means 3 cycles of 24 hours each at 4°C and 40 0 C alternately
- 35 g sodium lauroyl glycine and 35 g lauroyl glutamate, 30% active are dissolved in a phase consisting of 30 g glyceryl oleate, 60 g cetearyl isononanoate, 1O g jojoba oil and 2 g vitamin A palmitate.
- the mixture is heated to 60-70 0 C and the water is then added by degrees, taking care to ensure that the first part (approx. 20%) is well absorbed.
- a translucent lipogel is formed which, with the addition of the rest of the water, forms a nanoemulsion whose particles have a diameter of approx. 80 nm.
- the moisturising substance (5 g D-panthenol), fragrance and preservative are added at the end.
- Heat shock means 3 cycles of 24 hours each at 4 0 C and 40 0 C alternately
- 80 g potassium lauroyl oat amino acids, 30% active is dissolved in a phase consisting of 30 g glyceryl oleate, 60 g cetearyl isononanoate, 20 g decyl oleate, 20 g isopropyl palmitate, 20 g octyl palmitate and 10 g caprylic/capric triglyceride.
- the mixture is heated to 60-70 0 C and water is then added by degrees, taking care to ensure that the first part (approx. 20%) is well absorbed.
- a translucent lipogel is formed which, when all the water is added, forms a nanoemulsion whose particles have a diameter of approx. 80 nm.
- the moisturising substance (2 g Vitis vinifera), fragrance and preservative are added at the end.
- Heat shock means 3 cycles of 24 hours each at 4°C and 4O 0 C alternately
Abstract
Disclosed are nanoemulsions comprising lipoaminoacids and monoglycerides, diglycerides and polyglycerides of fatty acids as emulsifying system, and their use in the cosmetic, dermatological and pharmaceutical fields.
Description
NANOEMULSIONS COMPRISING LIPOAMINOACIDS AND MONO- GLYCERIDES, DIGLYCERIDES AND POLYGL YCERIDES OF FATTY ACIDS
This invention relates to nanoemulsions containing lipoaminoacids and monoglycerides, diglycerides and polyglycerides of fatty acids as emulsifiers.
Nanoemulsions are emulsions wherein the particle size of the internal phase is normally under 100 nm. This particle size is usually obtained by drastically reducing the interface tension of the system. According to Stokes' law, the sedimentation rate of the particles is directly proportional to twice the square of the particle diameter. Hence the smaller the particle size, the more stable the dispersion obtained.
Nanoemulsions can be used as a vehicle for transparent or translucent active ingredients with a particularly attractive appearance. Nanoemulsions are advantageously used in numerous applications. However, nanoemulsions are a system with a very delicate balance wherein even the addition of a single non-compatible component can jeopardise the stability and coagulation of the particles. Another known problem of nanoemulsions is their inability to incorporate large amounts of oil.
To eliminate these problems, known nanoemulsions have a relatively high content of emulsifiers such as fatty acids or ethoxylated or propoxylated fatty acids which, however, present problems of unsatisfactory skin tolerability and local toxicity. The problem of skin irritability is particularly felt, because nanoemulsions represent the ideal cosmetic and pharmaceutical vehicle for cosmetic active constituents; they easily permeate the first cell layer of the epidermis, and then release the necessary active constituents.
Nanoemulsions recently studied and developed as a vehicle for
cosmetic, dermatological and pharmaceutical active ingredients are described, for example, in US 2004445159 Al and EP-Al-1160005.
The nanoemulsions obtained so far contain synthetic surfactants deriving from ethylene or propylene oxide or phosphoric esters with a high surface energy which is advantageous in terms of stability but promotes penetration of the epidermis, leading to problems of skin intolerance, reddening and allergies due to ethylene and/or propylene oxide derivatives.
The use of phospholipids as emulsifiers has not yet proved wholly satisfactory as regards cosmetic emollient characteristics. It has now been discovered that stable, well-tolerated nanoemulsions can be obtained which are able to carry cosmetic or pharmaceutical active ingredients with a variety of chemico-physical characteristics by using at least one lipoaminoacid or a mixture thereof, associated with monoglycerides, diglycerides or polyglycerides of fatty acids, either individually or combined with one another.
The nanoemulsions according to the invention can contain a high percentage of lipids, and do not contain emulsifiers deriving from ethylene or propylene oxide, phosphoric esters, sulphated derivatives, etc.. They present a high level of skin tolerability and have a particle size of between 50 and 500 nm, and preferably between 50 and 100 nm.
Lipoaminoacids are obtained by reaction between fatty acids and at least one aminoacid or a mixture of aminoacids chosen from among glutamic acid, glycine, proline, arginine, valine, leucine, alanine, isoleucine, tryptophan, methionine, phenylalanine, serine, threonine, cysteine, tyrosine, asparagine, glutamine, aspartic acid, lysine, histidine, sarcosine, ornithine and desmosine.
Alternatively, lipoaminoacids can be obtained by reaction between fatty acids and carnitine, creatine or peptides such as carnosine, glutathione and
their physiologically equivalent derivatives.
The lipoaminoacids can be salified with alkaline metals, alkaline earths or amine bases, for example in the form of potassium, sodium, magnesium, triethanolamine or methylpropanolamine salts. The fatty acids are preferably chosen from among octanoic, decanoic, lauric, myristic, palmitic, oleic, stearic, linoleic, linolenic, erucic and behenic acid or mixtures thereof; alternatively, fatty acids obtained from coconut, palm, olive, sunflower, peanut, soya or sweet almond oil or other vegetable oils can be used. Lipoaminoacids are present in the nanoemulsions according to the invention in percentages of between 0.1 and 15% in weight of the total nanoemulsion, and preferably between 1 and 4%, while monoglycerides, diglycerides and polyglycerides of fatty acids are present in percentages of between 0.2 and 10% in weight of the total nanoemulsion, and preferably between 1 and 4%.
Lipoaminoacids are already used in cosmetics because they easily permeate the first layer of the epidermis, where they release the aminoacid portion and fatty acids that promote the restructuring and defence of the skin. Glycerol and polyglycerol esters of fatty acids represent the "co-emulsifier"; they are all soluble in the oily phase of the nanoemulsion, have a low interface energy, and do not affect the natural state of aggregation of the lipids and hydrophilic cutaneous substances.
The nanoemulsions according to the invention, like the normal emulsions used in cosmetics, can contain a large amount of lipids. The nanoemulsions according to the invention are highly homogenous monophase systems, and have an appearance ranging from semitransparent to sheer with beige/blue highlights, typical of nanoemulsions.
The nanoemulsion preparation methods described so far involve the use
of high pressures and temperatures; as a result, they are not easily reproduced at industrial level, and are expensive. However, the nanoemulsions to which this invention relates can be obtained with conventional emulsifying methods but with the advantage of considerable energy saving, in terms of both the mechanical energy required by the emulsifying devices and as regards heat, as they can be produced by pre-heating only the fatty phase containing the lipoaminoacid and the monoglycerides, diglycerides and polyglycerides of fatty acids, with a low input of mechanical energy. The industrial manufacturing processes are therefore reproducible and economical. The nanoemulsion obtained with the lipoaminoacid is dermatologically compatible, safe in toxicological terms, and can easily carry active constituents such as vitamins, alpha hydroxy acids, aminoacids, medicinal plant extracts and other cosmetologically functional substances to the surface skin layers. The nanoemulsions thus obtained can be used in the cosmetic, dermopharmaceutical and pharmaceutical industries due to their increased biological activity and skin penetration ability, and the improvement in the normal natural barrier functions of the cutaneous hydrolipid film.
The nanoemulsions according to the invention have low viscosity; they can be used "as is" and delivered by nebuliser spray or viscosified with conventional gelling agents.
The nanoemulsions according to the invention are also distinguished by their exceptional stability, even though they are free of viscosity at both high and low lipid concentrations. For example, the nanoemulsion according to the invention can contain between 1 and 60% of fatty phase and between 40 and 99% of water, demonstrating the great versatility of the system.
The following examples illustrate the invention in greater detail. EXAMPLE NO. 1
90 g of potassium lauroyl wheat amino acids is dissolved in a phase consisting of 80 g octyl palmitate, 30 g palm monoglycerides, 10 g jojoba oil and 5 g vitamin E. The mixture is heated to 60-700C and the water is then added by degrees, taking care to ensure that the first part (approx. 20%) is well absorbed.
At first a translucent lipogel is formed which, with the addition of the rest of the water, forms a nanoemulsion whose particles have a diameter of approx. 80 nm. Moisturising substances (20 g sodium lactate and 20 g sodium PCA), fragrance and preservative are added at the end.
Appearance: Translucent straw-coloured emulsion
Particle diameter: 50 nm
Centrifuge 10,000 rpm for 5 min: OK Heat shock: OK
("Heat shock" means 3 cycles of 24 hours each at 4°C and 400C alternately)
Stability at 3O0C for 6 months: OK
EXAMPLE NO. 2
60 g sodium lauroyl oat amino acids is dissolved in a phase consisting of 60 g caprylic/capric triglyceride, 20 g polyglyceryl isostearate, 1O g sweet almond oil and 2 g vitamin A palmitate. The mixture is heated to 60-700C and the water is then added by degrees, taking care to ensure that the first part
(approx. 20%) is well absorbed.
At first a translucent lipogel is formed which, with the addition of the rest of the water, forms a nanoemulsion whose particles have a diameter of approx. 80 nm. Moisturising substances (glycerin, fragrance and preservative) are added at the end.
Appearance: Translucent straw-coloured emulsion
Particle diameter: 100 nm
Centrifuge 10,000 rpm for 5 min: OK Heat shock: OK
("Heat shock" means 3 cycles of 24 hours each at 4°C and 400C alternately)
Stability at 300C for 6 months: OK
EXAMPLE NO. 3
35 g sodium lauroyl glycine and 35 g lauroyl glutamate, 30% active, are dissolved in a phase consisting of 30 g glyceryl oleate, 60 g cetearyl isononanoate, 1O g jojoba oil and 2 g vitamin A palmitate. The mixture is heated to 60-700C and the water is then added by degrees, taking care to ensure that the first part (approx. 20%) is well absorbed.
At first a translucent lipogel is formed which, with the addition of the rest of the water, forms a nanoemulsion whose particles have a diameter of approx. 80 nm. The moisturising substance (5 g D-panthenol), fragrance and preservative are added at the end.
Appearance: Translucent straw-coloured emulsion
Particle diameter: 70 nm
Centrifuge 10,000 rpm for 5 min: OK Heat shock: OK
("Heat shock" means 3 cycles of 24 hours each at 40C and 400C alternately)
Stability at 30°C for 6 months: OK
EXAMPLE NO. 4
80 g potassium lauroyl oat amino acids, 30% active, is dissolved in a phase consisting of 30 g glyceryl oleate, 60 g cetearyl isononanoate, 20 g decyl oleate, 20 g isopropyl palmitate, 20 g octyl palmitate and 10 g caprylic/capric triglyceride. The mixture is heated to 60-700C and water is then added by degrees, taking care to ensure that the first part (approx. 20%) is well absorbed.
At first a translucent lipogel is formed which, when all the water is added, forms a nanoemulsion whose particles have a diameter of approx. 80 nm. The moisturising substance (2 g Vitis vinifera), fragrance and preservative are added at the end.
Appearance: Ivory white translucent emulsion
Particle diameter: 60 nm Centrifuge 10,000 rpm for 5 min
Heat shock: OK
("Heat shock" means 3 cycles of 24 hours each at 4°C and 4O0C alternately)
Stability at 300C for 6 months: OK EXAMPLE NO. 5
20 g of magnesium lauroyl glutamate and 30 g of sodium cocoyl glycine, 30% active, are dissolved in a phase consisting of 30 g glyceryl olivate, 3O g decyl oleate, 20 g decyl oleate, 60 g octyl palmitate, 60 g cetearyl octanoate and 1O g wheatgerm oil. The mixture is heated to 60-700C and water is then added by degrees, taking care to ensure that the first part (approx. 20%) is well absorbed. At first a translucent lipogel is formed which, when all the water is added, forms a nanoemulsion whose particles have a diameter of approx. 80 nm. Moisturising substances (1O g sorbitol and 1O g D-panthenol), fragrance and preservative are added at the end.
Appearance: White/beige/blue emulsion Particle diameter: 100 nm
Centrifuge 10,000 rpm for 5 min
Heat shock: OK
("Heat shock" means 3 cycles of 24 hours each at 4°C and 4O0C
alternately)
Stability at 300C for 6 months: OK
Claims
1. Nanoemulsions comprising lipoaminoacids and monoglycerides, diglycerides or polyglycerides of fatty acids, either individually or combined with one another.
2. Nanoemulsions as claimed in claim 1, wherein the lipoaminoacids are obtained by reaction between fatty acids and at least one aminoacid or mixture of aminoacids chosen from among glutamic acid, glycine, proline, arginine, valine, leucine, alanine, isoleucine, tryptophan, methionine, phenylalanine, serine, threonine, cysteine, tyrosine, asparagine, glutamine, aspartic acid, lysine, histidine, sarcosine, ornithine and desmosine.
3. Nanoemulsions as claimed in claim 1, wherein the lipoaminoacids are obtained by reaction between fatty acids and carnitine, creatine, carnosine, glutathione and their physiologically equivalent derivatives.
4. Nanoemulsions as claimed in claim 1, 2 or 3, wherein the lipoaminoacids are salified with alkaline metals, alkaline earths or amine bases.
5. Nanoemulsions as claimed in claim 4, wherein the lipoaminoacids take the form of potassium, sodium, magnesium, triethanolamine or methylpropanolamine salts.
6. Nanoemulsions as claimed in any of claims 2 to 5, wherein the fatty acids are chosen from among octanoic, decanoic, lauric, myristic, palmitic, oleic, stearic, linoleic, linolenic, erucic and behenic acid or mixtures thereof.
7. Nanoemulsions as claimed in any of claims 2 to 5, wherein the fatty acids derive from coconut, palm, olive, sunflower, peanut, soya or sweet almond oil, or other vegetable oils.
8. Nanoemulsions as claimed in any of claims 1 to 7, wherein the lipoaminoacids are present in percentages of between 0.1 and 15% in weight of the total nanoemulsion.
9. Nanoemulsions as claimed in any of claims 1 to 8, wherein the monoglycerides, diglycerides and polyglycerides of fatty acids are present in percentages of between 0.2 and 10% in weight of the total nanoemulsion.
10. Nanoemulsions as claimed in any of claims 1 to 9, also containing active ingredients.
11. Nanoemulsions as claimed in claim 10, wherein the active ingredients are cosmetic or dermatological active ingredients.
12. Nanoemulsions as claimed in claim 11, wherein the active ingredients are chosen from among vitamins, polysaccharides, sugars, alpha hydroxyacids, micropigments, aminoacids, peptides, proteins and other active constituents of medicinal plants.
13. Nanoemulsions as claimed in any of claims 1 to 12, having a particle size of between 50 and 500 nm.
14. Cosmetic or pharmaceutical compositions comprising the nanoemulsions claimed in claims 1-13.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI2005A000218 | 2005-02-15 | ||
| ITMI20050218 ITMI20050218A1 (en) | 2005-02-15 | 2005-02-15 | NANOEMULSIONS INCLUDING LIPOAMINO ACIDS MONOGLYCERIDES DIGLYCERIDES POLYGLYCERIDES OF FATTY ACIDS |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2006087156A1 true WO2006087156A1 (en) | 2006-08-24 |
Family
ID=36190521
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP2006/001277 WO2006087156A1 (en) | 2005-02-15 | 2006-02-13 | Nanoemulsions comprising lipoaminoacids and monoglycerides, diglycerides and polyglycerides of fatty acids |
Country Status (2)
| Country | Link |
|---|---|
| IT (1) | ITMI20050218A1 (en) |
| WO (1) | WO2006087156A1 (en) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008104717A2 (en) * | 2007-02-14 | 2008-09-04 | Commissariat A L'energie Atomique | Method for preparing nano-emulsions |
| EP2222340A1 (en) * | 2007-11-28 | 2010-09-01 | Commonwealth Scientific and Industrial Research Organisation | Nanoemulsions |
| EP2366376A1 (en) * | 2010-03-05 | 2011-09-21 | Dr. Straetmans Chemische Produkte GmbH | Solubiliser preparation |
| US8168611B1 (en) | 2011-09-29 | 2012-05-01 | Chemo S.A. France | Compositions, kits and methods for nutrition supplementation |
| US8183227B1 (en) | 2011-07-07 | 2012-05-22 | Chemo S. A. France | Compositions, kits and methods for nutrition supplementation |
| WO2012009778A3 (en) * | 2010-07-22 | 2013-02-07 | Evidence Soluções Farmacêuticas Ltda Epp | A stable topical composition and a process for producing a stable topical composition |
| WO2012089184A3 (en) * | 2010-12-28 | 2013-07-04 | Gabriele Blume | Colloidal carrier system with penetration properties for encapsulating lipophilic active agents and oils for topical use |
| US9180210B2 (en) | 2008-08-14 | 2015-11-10 | Commissariat A L'energie Atomique Et Aux Energies Alternatives | Nanocrystal nano-emulsion |
| US9289517B2 (en) | 2008-08-14 | 2016-03-22 | Commissariat A L'energie Atomique Et Aux Energies Alternatives | Fluorescent emulsion of indocyanine green |
| US10092506B2 (en) | 2008-08-14 | 2018-10-09 | Commissariat A L'energie Atomique Et Aux Energies Alternatives | Encapsulation of lipophilic or amphiphilic therapeutic agents in nano-emulsion |
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| WO1998015255A1 (en) * | 1996-10-10 | 1998-04-16 | Beiersdorf Ag | Cosmetic or dermatological microemulsions |
| EP1160005A1 (en) * | 2000-05-22 | 2001-12-05 | L'oreal | Nanoemulsion based on anionic polymers, and uses thereof especially in the cosmetic, dermatological, pharmaceutical and/or ophthalmic fields |
| EP1174180A1 (en) * | 2000-07-21 | 2002-01-23 | Clariant GmbH | Fine emulsions |
| EP1250906A2 (en) * | 2001-04-20 | 2002-10-23 | Hans Schwarzkopf GmbH & Co. KG | Compositions for skin and/or hair treatment |
| EP1502644A2 (en) * | 2003-07-28 | 2005-02-02 | Cognis Deutschland GmbH & Co. KG | Combination of emulsifiers, emulsion containing the same and process for preparing the same. |
-
2005
- 2005-02-15 IT ITMI20050218 patent/ITMI20050218A1/en unknown
-
2006
- 2006-02-13 WO PCT/EP2006/001277 patent/WO2006087156A1/en not_active Application Discontinuation
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998015255A1 (en) * | 1996-10-10 | 1998-04-16 | Beiersdorf Ag | Cosmetic or dermatological microemulsions |
| EP1160005A1 (en) * | 2000-05-22 | 2001-12-05 | L'oreal | Nanoemulsion based on anionic polymers, and uses thereof especially in the cosmetic, dermatological, pharmaceutical and/or ophthalmic fields |
| EP1174180A1 (en) * | 2000-07-21 | 2002-01-23 | Clariant GmbH | Fine emulsions |
| EP1250906A2 (en) * | 2001-04-20 | 2002-10-23 | Hans Schwarzkopf GmbH & Co. KG | Compositions for skin and/or hair treatment |
| EP1502644A2 (en) * | 2003-07-28 | 2005-02-02 | Cognis Deutschland GmbH & Co. KG | Combination of emulsifiers, emulsion containing the same and process for preparing the same. |
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008104717A3 (en) * | 2007-02-14 | 2009-02-19 | Commissariat Energie Atomique | Method for preparing nano-emulsions |
| WO2008104717A2 (en) * | 2007-02-14 | 2008-09-04 | Commissariat A L'energie Atomique | Method for preparing nano-emulsions |
| EP2222340A1 (en) * | 2007-11-28 | 2010-09-01 | Commonwealth Scientific and Industrial Research Organisation | Nanoemulsions |
| US9649275B2 (en) | 2007-11-28 | 2017-05-16 | Commonwealth Scientific And Industrial Research Organisation | Nanoemulsions |
| EP2222340A4 (en) * | 2007-11-28 | 2013-01-23 | Commw Scient Ind Res Org | Nanoemulsions |
| US9180210B2 (en) | 2008-08-14 | 2015-11-10 | Commissariat A L'energie Atomique Et Aux Energies Alternatives | Nanocrystal nano-emulsion |
| US10092506B2 (en) | 2008-08-14 | 2018-10-09 | Commissariat A L'energie Atomique Et Aux Energies Alternatives | Encapsulation of lipophilic or amphiphilic therapeutic agents in nano-emulsion |
| US9289517B2 (en) | 2008-08-14 | 2016-03-22 | Commissariat A L'energie Atomique Et Aux Energies Alternatives | Fluorescent emulsion of indocyanine green |
| EP2366376A1 (en) * | 2010-03-05 | 2011-09-21 | Dr. Straetmans Chemische Produkte GmbH | Solubiliser preparation |
| WO2012009778A3 (en) * | 2010-07-22 | 2013-02-07 | Evidence Soluções Farmacêuticas Ltda Epp | A stable topical composition and a process for producing a stable topical composition |
| US9572770B2 (en) | 2010-07-22 | 2017-02-21 | Evidence Solucões Farmacêuticas Ltda Epp | Stable topical composition and a process for producing a stable topical composition |
| WO2012089184A3 (en) * | 2010-12-28 | 2013-07-04 | Gabriele Blume | Colloidal carrier system with penetration properties for encapsulating lipophilic active agents and oils for topical use |
| US9161921B2 (en) | 2010-12-28 | 2015-10-20 | Gabriele Blume | Colloidal carrier system with penetration properties for encapsulating lipophilic active agents and oils for topical use |
| US8183227B1 (en) | 2011-07-07 | 2012-05-22 | Chemo S. A. France | Compositions, kits and methods for nutrition supplementation |
| US8545896B2 (en) | 2011-09-29 | 2013-10-01 | Chemo S. A. France | Compositions, kits and methods for nutrition supplementation |
| US8168611B1 (en) | 2011-09-29 | 2012-05-01 | Chemo S.A. France | Compositions, kits and methods for nutrition supplementation |
Also Published As
| Publication number | Publication date |
|---|---|
| ITMI20050218A1 (en) | 2006-08-16 |
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