WO2015082943A1 - Method of entrapment of plant oils and specifically olive oil with the use of specialized edible liposomes without phospholipids for use and applications on foods and specifically on meat, dairy and fish products - Google Patents

Method of entrapment of plant oils and specifically olive oil with the use of specialized edible liposomes without phospholipids for use and applications on foods and specifically on meat, dairy and fish products Download PDF

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Publication number
WO2015082943A1
WO2015082943A1 PCT/GR2014/000067 GR2014000067W WO2015082943A1 WO 2015082943 A1 WO2015082943 A1 WO 2015082943A1 GR 2014000067 W GR2014000067 W GR 2014000067W WO 2015082943 A1 WO2015082943 A1 WO 2015082943A1
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oil
product
liposome
edible
plant
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PCT/GR2014/000067
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French (fr)
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WO2015082943A4 (en
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YIOURNAS.Konstantinos
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Sales Development Consultants Ltd
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Publication of WO2015082943A4 publication Critical patent/WO2015082943A4/en

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/69—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
    • A61K47/6905—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit the form being a colloid or an emulsion
    • A61K47/6911—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit the form being a colloid or an emulsion the form being a liposome
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
    • A23D7/005—Edible oil or fat compositions containing an aqueous phase, e.g. margarines characterised by ingredients other than fatty acid triglycerides
    • A23D7/0053—Compositions other than spreads
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
    • A23D7/01—Other fatty acid esters, e.g. phosphatides
    • A23D7/011—Compositions other than spreads
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
    • A23D7/02—Edible oil or fat compositions containing an aqueous phase, e.g. margarines characterised by the production or working-up
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L13/00—Meat products; Meat meal; Preparation or treatment thereof
    • A23L13/40—Meat products; Meat meal; Preparation or treatment thereof containing additives
    • A23L13/42—Additives other than enzymes or microorganisms in meat products or meat meals
    • A23L13/43—Addition of vegetable fats or oils; Addition of non-meat animal fats or oils; Addition of fatty acids
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L17/00—Food-from-the-sea products; Fish products; Fish meal; Fish-egg substitutes; Preparation or treatment thereof
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
    • A23L29/10—Foods or foodstuffs containing additives; Preparation or treatment thereof containing emulsifiers
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/115—Fatty acids or derivatives thereof; Fats or oils
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L35/00—Food or foodstuffs not provided for in groups A23L5/00 – A23L33/00; Preparation or treatment thereof
    • A23L35/10—Emulsified foodstuffs
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23P—SHAPING OR WORKING OF FOODSTUFFS, NOT FULLY COVERED BY A SINGLE OTHER SUBCLASS
    • A23P10/00—Shaping or working of foodstuffs characterised by the products
    • A23P10/30—Encapsulation of particles, e.g. foodstuff additives
    • 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
    • A61K9/127—Liposomes

Definitions

  • the liposome structures are concentric lipid spheres consisting of about 4 to 7 spherical membranes pushed to the surface of the structure, thus creating an "empty" space in the center available for loading with lipophylic materials, hydrophylic materials, or both.
  • the membranes resemble to a great degree those of living animal cells.
  • the available volume for loading is about 80% the volume of the liposome. In this space it is possible to entrap lipophylic materials up to 40% of the volume and in the remaining space hydrophylic materials.
  • the outer surface is always hydrophylic and could be charged positive or negative (the result of the selection of the membrane building materials). Thus, they are held electrostatically in the lattice of the final food product under normal atmospheric pressure without the use of vacuum.
  • the lipophylic membrane building materials of this specific liposome system along with the plant oils for loading are charged in an appropriate double wall vessel with temperature controls, equipped with an impeller type mixer and homogenizer.
  • the temperature to be achieved is regulated to reach the melting point of the solids under continuous agitation until the entire mass is clear.
  • the hydrophylic materials in this case deionized water
  • the temperature is regulated so it approaches the temperature of the lipophylic materials without exceeding it.
  • the homogenizer of the vessel with the lipophylic phase is energized and the hydrophylic phase is rapidly transferred by means of an appropriate pump into the vessel with the lipophylic phase.
  • the hydraulic and mechanical shear generated by the homogenizer forms the liposomes and simultaneously entraps a microscopic mass of the oil in the center of the vesicle, (entrapment of oils up to 40% of the liposome volume).
  • the final product at room temperature has the texture of a thick cream and color almost white with neutral taste. It is stored in the refrigerator at 4 degrees C in appropriate sealed containers without preservatives. Storage time is at least three months at 4 degrees C.
  • the liposome product is characterized by its ability to go through the pasteurization process at 77-80° C and in time appropriate for full pasteurization (1 to 3 hours) depending on product, without breaking up.
  • the product After very thorough mixing, the product is homogenously dispersed throughout the mass, then it is encased in the appropriate membrane casing and goes through pasteurization specific by product.
  • the product is added after the pasteurization process and only when the temperature has come down to 40-42 degrees C with simultaneous addition of bacterial cultures specific for the final product (yogurt, cheeses).
  • the final product which begins as skimmed milk has olive oil entrapped in liposomes homogenously dispersed at a percentage chosen by the manufacturer.
  • the liposomes without phospholipids belong to a unique category of liposomes manufactured by a unique process.
  • the liposomes without phospholipids can be formed by a broad spectrum of emulsifiers.
  • the liposome has from one or two up to seven bilayer membranes encasing a large amorphous "empty" space. Each membrane consists of emulsifier molecules in a double row. This space occupies the greater part of the liposome volume and it is capable of large loading with lipophylic and hydrophylic substances.
  • the liposomes without phospholipids can be manufactured very fast in large volumes with a cost very similar to those of a simple emulsion.
  • the purpose of the invention is to replace the animal fat with plant oils and specifically with olive oil by using a specific edible liposome system without phospholipids capable of remaining intact during the pasteurization temperatures. This is accomplished by the proper selection of the building materials of the liposome membranes and the correct ratio among them.
  • l The lipophylic membrane building materials along with the plant oils to be encapsulated are charged into a proper double wall vessel with controlled temperature and equipped with a propeller type mixer and homogenizer. The temperature is regulated so it reaches the melting point of the solids and maintained until the entire mass is clear. 2.
  • the hydrophylic components in this case dionized water
  • the temperature is regulated so it approaches the final temperature of the lipophylic phase without going above it.
  • the hydraulic and mechanical shear that is generated by the homogenizer forms the liposomes and at the same time entraps a microscopic quantity of oil in each liposome. (Entrapment of oils up to 40% of the liposome volume).
  • the resulting mass is quickly cooled with the homogenizer running until the product approaches room temperature.
  • the final product is the complete encapsulation of plant oils (olive oil) inside the liposome system without free oil existing outside the formed liposomes.
  • the final product has a creamy but solid texture slightly off white with almost neutral taste. It is stored in the refrigerator at temperatures around 4 degrees C in sealed containers without preservatives. The storage time is at least three months at 4 degrees C.
  • the product is added towards the end of the process and it is evenly dispersed throughout the mass under atmospheric pressure without the use of vacuum.
  • the final meat products are encased in the appropriate casings and go through the pasteurization process specific for each product.
  • the product is added after the pasteurization process at temperatures around 40 -42 degrees C, with the simultaneous addition of microorganisms appropriate for each product ( yogurt, cheeses, etc).
  • the final product which starts as skim milk has encapsulated olive oil uniformly dispersed throughout the mass at a percentage chosen by the manufacturer. 3.1n the fish products sector the product is added towards the end of the process and is uniformly dispersed under normal atmospheric pressure without the use of vacuum.

Abstract

In our case, the liposome system is fully edible and made up with ingredients allowed by the food code. Specifically, it is made from products of plant fatty acids, phytosterols, emulsifiers and plant waxes. The selection and the ratio of the above mentioned ingredients is regulated so the system remains whole and intact at the temperature-time exposure requirement for the specific meat, dairy and fish products. With this specialized liposome system we are succeeding in replacing the animal fats with edible oils and specifically olive oil. The olive oil is uniformly dispersed in microscopic encapsulated quantities in the edible liposome system and it is held firmly in the lattice of the final product at atmospheric pressure without the use of vacuum.

Description

Method of entrapment of plant oils and specifically olive oil with the use of specialized edible liposomes without phospholipids for use and applications on foods and specifically on meat, dairy and fish products.
In this specific class of liposomes without phospholipids (Paucilamellar) the liposome structures are concentric lipid spheres consisting of about 4 to 7 spherical membranes pushed to the surface of the structure, thus creating an "empty" space in the center available for loading with lipophylic materials, hydrophylic materials, or both.
The membranes resemble to a great degree those of living animal cells. The available volume for loading is about 80% the volume of the liposome. In this space it is possible to entrap lipophylic materials up to 40% of the volume and in the remaining space hydrophylic materials.
In other words, in the same space lipophylic and hydrophylic materials coexist. The size of this unique class of liposomes without phospholipids varies from about 300 nanometers to about 1000 nanometers (one micron).
The outer surface is always hydrophylic and could be charged positive or negative (the result of the selection of the membrane building materials). Thus, they are held electrostatically in the lattice of the final food product under normal atmospheric pressure without the use of vacuum.
1. The lipophylic membrane building materials of this specific liposome system along with the plant oils for loading are charged in an appropriate double wall vessel with temperature controls, equipped with an impeller type mixer and homogenizer. The temperature to be achieved is regulated to reach the melting point of the solids under continuous agitation until the entire mass is clear.
2. The hydrophylic materials (in this case deionized water) are charged in a similar vessel and the temperature is regulated so it approaches the temperature of the lipophylic materials without exceeding it. 3. The homogenizer of the vessel with the lipophylic phase is energized and the hydrophylic phase is rapidly transferred by means of an appropriate pump into the vessel with the lipophylic phase.
The hydraulic and mechanical shear generated by the homogenizer forms the liposomes and simultaneously entraps a microscopic mass of the oil in the center of the vesicle, (entrapment of oils up to 40% of the liposome volume).
Quick cooling of the mass follows with the continuous use of the homogenizer until the product approaches room temperature. In the final product we have complete encapsulation of the plant oil (olive oil) in the liposome system without any free oil remaining outside the vesicles.
The final product at room temperature has the texture of a thick cream and color almost white with neutral taste. It is stored in the refrigerator at 4 degrees C in appropriate sealed containers without preservatives. Storage time is at least three months at 4 degrees C.
The liposome product is characterized by its ability to go through the pasteurization process at 77-80° C and in time appropriate for full pasteurization (1 to 3 hours) depending on product, without breaking up.
From this point on the product is considered as an intermediate food ingredient and is sold as such. The containers are sealed and ready for use in the food industry.
1. In the process meat sector the product is added towards the end of the process under regular atmospheric pressure without use of a vacuum.
After very thorough mixing, the product is homogenously dispersed throughout the mass, then it is encased in the appropriate membrane casing and goes through pasteurization specific by product.
2. In the dairy products sector the product is added after the pasteurization process and only when the temperature has come down to 40-42 degrees C with simultaneous addition of bacterial cultures specific for the final product (yogurt, cheeses). The final product, which begins as skimmed milk has olive oil entrapped in liposomes homogenously dispersed at a percentage chosen by the manufacturer.
The liposomes without phospholipids belong to a unique category of liposomes manufactured by a unique process.
They were developed in order to solve problems inherent to phospholipid liposomes, specifically, their difficulty in manufacturing, their very small loading capacity, great manufacturing cost, very sensitive and unstable behavior and high cost of raw materials.
The liposomes without phospholipids can be formed by a broad spectrum of emulsifiers. In our case, the liposome has from one or two up to seven bilayer membranes encasing a large amorphous "empty" space. Each membrane consists of emulsifier molecules in a double row. This space occupies the greater part of the liposome volume and it is capable of large loading with lipophylic and hydrophylic substances. The liposomes without phospholipids can be manufactured very fast in large volumes with a cost very similar to those of a simple emulsion.
The purpose of the invention is to replace the animal fat with plant oils and specifically with olive oil by using a specific edible liposome system without phospholipids capable of remaining intact during the pasteurization temperatures. This is accomplished by the proper selection of the building materials of the liposome membranes and the correct ratio among them. l .The lipophylic membrane building materials along with the plant oils to be encapsulated are charged into a proper double wall vessel with controlled temperature and equipped with a propeller type mixer and homogenizer. The temperature is regulated so it reaches the melting point of the solids and maintained until the entire mass is clear. 2. The hydrophylic components (in this case dionized water) are added in a similar vessel and the temperature is regulated so it approaches the final temperature of the lipophylic phase without going above it.
3. The homogenizer of the vessel holding the lipophylic phase is engaged and the hydrophylic phase with a proper transfer pump is quickly added to the lipophylic phase.
The hydraulic and mechanical shear that is generated by the homogenizer forms the liposomes and at the same time entraps a microscopic quantity of oil in each liposome. (Entrapment of oils up to 40% of the liposome volume).
The resulting mass is quickly cooled with the homogenizer running until the product approaches room temperature. The final product is the complete encapsulation of plant oils (olive oil) inside the liposome system without free oil existing outside the formed liposomes. At room temperature, the final product has a creamy but solid texture slightly off white with almost neutral taste. It is stored in the refrigerator at temperatures around 4 degrees C in sealed containers without preservatives. The storage time is at least three months at 4 degrees C.
From this point forward it is considered as an intermediate foot ingredient and is sold as such. The containers are sealed and ready for use in the food industry.
1. In the meat products sector the product is added towards the end of the process and it is evenly dispersed throughout the mass under atmospheric pressure without the use of vacuum.
The final meat products are encased in the appropriate casings and go through the pasteurization process specific for each product.
2. In the dairy products sector the product is added after the pasteurization process at temperatures around 40 -42 degrees C, with the simultaneous addition of microorganisms appropriate for each product ( yogurt, cheeses, etc).
The final product which starts as skim milk has encapsulated olive oil uniformly dispersed throughout the mass at a percentage chosen by the manufacturer. 3.1n the fish products sector the product is added towards the end of the process and is uniformly dispersed under normal atmospheric pressure without the use of vacuum.
References:
1. Gebicki, J.M. and Hicks, M., 1976, Preparation and properties of vesicles enclosed by fatty acid membranes. Chem.Phys. Lipids 16, 142-160.
2. Hargreaves, W. R. And Dreamer, D. W., 1978, Liposomes from ionic, single chain amphiphiles, Biochemistry 17, 3759-3768.
3. unitake, T., Nakashima, N., Hayashida, S., and Yonemori, K.1979. Chiral, synthetic bilayer membranes. Chem. Lett., 1413- 1416.
4. Schenk, P., Ausborn, m., Bendas, F., Nuhn, P., Arndt, D. and Meyer, H. W. The preparation and characterization of lipid vesicles containing esters of sucrose and fatty acids, 1989, J. Microencapsulation 6, 95-103
5. Wallach, D.F.H. and Philippot, J., 1989, Method of manufacturing unilamellar lipid vesicles. U.S. Patent 4, 853,228.
6. Wallach, D.F.H. , 1989, Method of producing high-aquerous volume multilamellar vesicles. U.S. Patent 4, 855. 090
7. Wallach, D.F.H. and Yiournas, C, 1990, Method and apparatus for producing lipid vesicles. U.S. Patent 4, 895. 452.
8. Scott, H. L. and Kalaskar, S., 1989, Lipid chains and cholesterol in model membranes, Biochemistry 28, 3687-3691.

Claims

1. Method of entrapping of plant oils in a specialized edible liposome system without phospholipids, which is characterized by the following steps.
A. The lipophylic components of the edible liposome membranes are charged into a double wall vessel with controlled temperature and equipped with an impeller type mixer and homogenizer. In the same vessel the plant oil to be entrapped is also added. The components that are added are:
1. Plant oil (olive oil)
2. phytosterols
3. Plant wax derived from a Brazillian palm tree (palm wax)
4. emulsifiers (esters of fatty acids with propylene glycol )
5. emulsifier - polysorbate 80
B. A similar vessel is charged with the hydrophylic phase which in this case is dionized water.
C. The lipophylic phase is heated under continuous agitation until it becomes clear and maintained at 80-82 degrees C. The hydrophylic phase is also heated and maintained at 75- 77 degrees C.
D. The two phases are brought into contact quickly under continuous homogenization. Progressive cooling follows until the product approaches 30 degrees C.
E. Next, the product is transferred into appropriate containers and is stored in the refrigerator at 4 degrees C.
2. Method of entrapment of plant oils in a specialized edible liposome system without phospholipids according to claim number one (1) , where the plant oils could be corn oil, sunflower seed oil, soybean oil, argan oil, linseed oil, and any other edible oil.
3. Method of entrapment of plant oils in a specialized edible liposome system without phospholipids according to claim number one (1 ), where the plant oil is olive oil.
4. The liposome product which is produced according to the method of claims 1 and 3, characterized in that it has the ability to remain intact during the pasteurization process, i.e at 77-80 degrees C and for the time required for full pasteurization, from 1 to 3 hours depending on the meat product.
5. Use of the liposome product according to claims 1 , 3, and 4 in the manufacturing process of meat products, dairy products, fish products, and bread products.
6. Use of the liposome product according to claims 1 , 3 and 4 in meat and dairy production processing by replacing the animal fat with olive oil and phytosterols.
7. The product produced according to claim 1 characterized in that it remains whole and intact at a pasteurization temperature of 77-80 degrees C.
8. The product produced according to claim 1 characterized in that it remains whole and intact at the pasteurization temperature for 1 -3 hours according to product pasteurization time required.
9. The liposome product according to the previous claims characterized in that it has encapsulated olive oil up to 40% of its volume.
10. The final liposome product, characterized in that no free plant oil is present in the participating liposomes.
PCT/GR2014/000067 2013-12-05 2014-12-03 Method of entrapment of plant oils and specifically olive oil with the use of specialized edible liposomes without phospholipids for use and applications on foods and specifically on meat, dairy and fish products WO2015082943A1 (en)

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Application Number Priority Date Filing Date Title
GR20130100675 2013-12-05
GR20130100675A GR1008481B (en) 2013-12-05 2013-12-05 Method for the confinement of plant oils (olive oil) with use of specific edible liposomes without phospholipids- application of said method in food, charcuterie, dairy products and fish preparations

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WO2015082943A1 true WO2015082943A1 (en) 2015-06-11
WO2015082943A4 WO2015082943A4 (en) 2015-07-30

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US4855090A (en) 1987-03-13 1989-08-08 Micro-Pak, Inc. Method of producing high aqueous volume multilamellar vesicles
US4895452A (en) 1988-03-03 1990-01-23 Micro-Pak, Inc. Method and apparatus for producing lipid vesicles
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WO1995016436A1 (en) * 1993-12-15 1995-06-22 Micro-Pak, Inc. Lipid vesicles containing avocado oil unsaponifiables
WO1995022989A1 (en) * 1994-02-24 1995-08-31 Micro-Pak, Inc. Vaccines containing paucilamellar lipid vesicles as immunological adjuvants
US5756014A (en) * 1997-04-11 1998-05-26 Igen, Inc. Heat resistant lipid vesicles
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Title
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