Process for preparing an oil-free composition comprising phospholipids

Abstract

The present invention relates to a method for extracting oil from an oil-containing phospholipid composition, said method comprising the steps of: (a) providing said oil-containing phospholipid composition, said composition comprising phospholipids and oil, the amount of said oil being between 20 and 80 wt% relative to the total weight of the oil composition; (b) mixing water with the oil-containing phospholipid composition to obtain a water-containing composition, wherein the weight ratio of composition to water is between 6.0:1.0 and 1.3:1.0; (c) separating said water-containing composition into an oil-rich fraction and an oil-poor fraction, said oil-poor fraction comprising water and phospholipids; and (d) removing said separated oil-rich fraction to obtain a water-containing oil-poor fraction comprising phospholipids; (e) optionally drying said water-containing oil-poor fraction to obtain a dried oil-poor fraction comprising phospholipids.

Description

Technical Field

[0001] This invention relates to a method for extracting oil from an oil composition containing phospholipids. The invention also relates to an oil-free phospholipid composition obtained by the method of the invention, and its use in food, beverages, nutritional products, dietary supplements, animal feed, personal care applications, pharmaceutical applications, and industrial applications. Background Technology

[0002] Phospholipid-containing plant compositions are byproducts of oil production. As natural emulsifiers with excellent technical and nutritional-physiological properties, these compositions are highly valuable across various industries, particularly the food industry. Today, over 800 million people consume phospholipid-containing products daily. They are increasingly replacing synthetic emulsifiers and stabilizers.

[0003] Demand for naturally processed products, including those containing phospholipids, is also rising. In many food applications, a shift is occurring towards cleaner ingredients. Specifically, oil-free compositions containing phospholipids are highly desirable due to their high emulsifying power and excellent water dispersibility. Unfortunately, such oil-free compositions are typically produced using organic solvents (such as acetone), which is undesirable for some products. Therefore, there is a need for cleaner, oil-free compositions containing phospholipids.

[0004] "Degumming" is a term given to methods for removing phospholipids, particularly from crude oil. Simple degumming methods involve mixing only water and oil and separating the resulting mixture into an oil component and an aqueous component, which contains, in particular, some phospholipids. An example of such a method is given in CA-A-522398, which describes a water degumming method for rice bran oil. Rice bran oil contains a high proportion of wax, and the method described in CA-A-522398 involves heating the oil / water mixture to hydrate the gum, then slowly cooling the mixture to allow wax crystals to coalesce, and thus separating them from the aqueous component. It is thought that reheating the separated aqueous or sludge component allows for the extraction of wax as well as any entrained oil.

[0005] US-A-4 162 260 describes another attempt to remove phospholipids from triglyceride oils, which proposes removing impurities from triglyceride oils by increasing the content of hydrated phospholipids before degumming.

[0006] However, known methods (such as degumming methods) have problems because it is difficult to extract most of the oil. Even after repeating the method many times, a significant amount of oil remains in the phospholipid-containing composition. Therefore, there is a need for a method that can extract most of the oil content and provide a substantially oil-free phospholipid composition. Summary of the Invention

[0007] This invention provides a method for extracting oil from an oil-containing phospholipid composition, the method comprising the following steps:

[0008] a) Provides an oil-containing phospholipid composition comprising phospholipids and oil, wherein the amount of oil is between 20% by weight and 80% by weight relative to the total weight of the oil composition;

[0009] b) Mixing water with an oil-containing phospholipid composition to obtain an aqueous composition, wherein the weight ratio of the composition to water is between 6.0:1.0 and 1.3:1.0;

[0010] c) Separating the aqueous composition into an oil-rich fraction and an oil-lean fraction, the oil-lean fraction comprising water and phospholipids; and

[0011] d) Remove the separated oil-rich fraction to obtain a water-containing oil-poor fraction containing phospholipids;

[0012] e) Optionally, the aqueous lean oil fraction is dried to obtain a dried lean oil fraction containing phospholipids.

[0013] The inventors have observed that the method according to the invention (hereinafter “the method of the invention”) can produce lean oil compositions containing phospholipids in an efficient and economical manner. Specifically, the lean oil compositions obtained by the method of the invention may contain a small amount of residual oil, such a small amount that it has never been achieved to date with the inventors’ knowledge.

[0014] Other advantages of the invention will become apparent from the detailed description given below. Detailed Implementation

[0015] This invention relates to a method for extracting oil from a composition comprising phospholipids and oil (hereinafter referred to as the method of this invention).

[0016] The oil-containing phospholipid composition comprises phospholipids and oil, wherein the amount of oil is between 20% by weight and 80% by weight relative to the total weight of the oil composition. Preferably, the composition contains between 25% by weight and 75% by weight, and most preferably between 30% by weight and 70% by weight.

[0017] Oil-containing phospholipid compositions can be obtained from crude oil, for example, by degumming the crude oil. Crude oil can be obtained from plants, animals, algae, and / or microorganisms, for example, by pressing or extraction using organic solvents. Hot pressing and cold pressing methods are known for recovering crude oil. Extraction methods, such as hexane extraction, can also be used. However, various alternative supply variants are contemplated. The crude oil herein does not necessarily have to be obtained directly from living organisms, but may have been used once or multiple times for its intended purpose, as in the case of frying oils or industrial oils. Specifically, as used herein, the term "crude oil" encompasses compositions of biological origin, which may be obtained from plants, algae, animals, and / or microorganisms, and preferably has a water content of up to 10% by weight relative to the weight of the oil, and a fraction of at least 75% by weight of alkanes and / or cyclic aromatics and / or monoglycerides / diglycerides / triglycerides (acylglycerols).

[0018] If the crude oil is derived from algae, the algal oil is preferably selected from: oil-rich Neochlorisoleoabundans, Scenedesmus dimorphus, Euglena gracilis, Phaeodactylum tricornutum, Pleurochrysis carterae, Prymnesium parvum, Tetraselmis chui, Tetraselmis suecica, Isochrysis galbana, Nannochloropsis salina, and Botryococcus. oils such as braunii, Dunaliella tertiolecta, Nannochloris, Spirulina, Chlorophyceae, Bacilliarophyta, or mixtures thereof.

[0019] Preferably, the crude oil is a vegetable oil. Preferably, the vegetable oil is selected from the following oils: acai oil, prickly palm oil, almond oil, babassu oil, blackcurrant seed oil, borage seed oil, rapeseed oil, cashew oil, coconut oil, coriander oil, corn oil, cottonseed oil, sea buckthorn seed oil, flaxseed oil, grapeseed oil, hazelnut oil, other nut oils, jojoba oil, macadamia nut oil, mango kernel oil, oxalis oil, mustard oil, cow's hoof oil; olive oil, palm oil, palm kernel oil, palm oil extract, peanut oil, pecan oil, pine nut oil, pistachio oil, rice germ oil, safflower oil, camellia oil, sesame oil, shea butter, soybean oil, sunflower oil, ailanthus oil, walnut oil, "natural" grade oils having fatty acid compositions improved through genetically modified organisms (GMOs) or conventional breeding, and mixtures of the aforementioned oils.

[0020] Most preferably, the crude oil is selected from the following vegetable oils: sunflower oil, safflower oil, rapeseed oil, rice bran oil, olive oil, soybean oil, corn oil, cottonseed oil, sesame oil, or palm oil extract, palm kernel oil, their corresponding high-oleic acid varieties, and mixtures of two or more of them. In terms of fatty acid distribution, the high-oleic acid variety is an oil containing at least 40%, at least 50%, at least 60%, at least 70%, and preferably at least 80% oleic acid. Particularly preferred liquid oils are sunflower oil, rapeseed oil, soybean oil, palm oil extract (mono- or di-fractional), and palm kernel oil.

[0021] The content of the phospholipid-containing composition used according to the present invention will depend on the crude oil from which the composition is obtained. For the purposes of the present invention, the oil composition contains phospholipids and between 20% and 80% by weight of oil, which is an oil naturally present in crude oil. The oil composition may also contain waxes, gums, glucosides, etc., and water. Preferably, the oil composition contains at most 50% by weight, more preferably at most 35% by weight, and most preferably at most 25% by weight of water relative to the weight of the composition, provided that the amount of oil in the composition is within the desired range. Preferably, the amount of water is at least 1% by weight, more preferably at least 3% by weight, and most preferably at least 5% by weight.

[0022] Oil-containing phospholipid compositions contain phospholipids. The nature and content of phospholipids in the composition can vary depending on the crude oil. Phospholipids (also called phospholipids) are phosphorus-containing organic substances with fatty properties. Phospholipids differentiate into non-hydrated phospholipids (NHP) and hydrated phospholipids (HP). Examples of hydrated or partially hydrated phospholipids include phosphatidylinositol or its salts, phosphatidylcholine, and phosphatidylethanolamine. Examples of non-hydrated phospholipids are salts of phosphatidic acids (e.g., their calcium or magnesium salts). Typical examples of cations in phospholipids are sodium, potassium, calcium, etc.

[0023] Preferably, the oil-containing phospholipid composition is obtained from crude oil through a degumming operation. In this operation, water is typically added to the crude oil to precipitate the phospholipids and aid in their removal from the crude oil. If the phospholipids are hydrated, they are hydrated by adding water to the crude oil. The precipitated phospholipids can be separated from the oil by centrifugation. Non-hydrated phospholipids can be converted to a hydrated form, for example, by adding an acid, and / or can be removed by filtration or the use of a solvent. Specifically, adding an acid may include adding a diluted acid or, equally preferably, adding a concentrated acid in combination with subsequent addition of water. Adding acid is referred to as acid degumming, while adding water is referred to as water degumming. Preferably, acid degumming is carried out by dispersing an acid or anhydride in the crude oil having a pH of at least 0.5, as measured in a molar aqueous solution at 20°C, and dispersing 0.2% to 5% water by weight of the crude oil in the resulting mixture, and holding the resulting mixture at a temperature below 40°C for at least 5 minutes, and then separating it into an oil fraction and a sludge fraction.

[0024] After degumming, (i) a degummed oil fraction is obtained, which still contains residual phospholipid fractions, primarily non-hydratable phospholipids, and (ii) a phospholipid-rich sludge fraction is obtained, which primarily contains hydratable phospholipids and contains oil and some water. The sludge fraction is used for the purposes of this invention and is referred to herein as an oil-containing phospholipid composition for simplicity. The degumming method can be readily and routinely carried out to provide an oil-containing phospholipid composition suitable for use in this invention.

[0025] Preferably, the oil-containing phospholipid composition contains phospholipids in an amount (as measured by the acetone-insoluble matter (AI) method shown in the Method section) of at least 20% by weight relative to the weight of the composition, more preferably at least 40% by weight, and most preferably at least 60% by weight, provided that the oil content of the composition is within the desired range. The amount of phospholipids is preferably at most 75% by weight, more preferably at most 73% by weight, and most preferably at most 70% by weight. The AI ​​concentration can be easily adjusted by a skilled technician, for example, by changing parameters of the degumming process, such as the amount of water used for degumming (using a lower amount of water will result in a higher AI).

[0026] The method of the present invention also implies a step of mixing water with the oil-containing phospholipid composition in a carefully selected ratio. The inventors have observed that when the weight ratio of the composition to water is between 6.0:1.0 and 1.3:1.0, it is advantageous to extract oil from the composition. Preferably, the weight ratio of the composition to water is between 6.0:1.0 and 1.5:1.0, more preferably between 5.5:1.0 and 1.5:1.0, even more preferably between 5.0:1.0 and 1.5:1.0, even more preferably between 4.0:1.0 and 2.0:1.0, and most preferably between 3.5:1.0 and 2.5:1.0. The mixing of water with the oil-containing phospholipid composition can be carried out using conventional equipment in the art, such as mixers, including static mixers, dynamic mixers, high-shear mixers, and centrifugal pumps.

[0027] Preferably, before mixing the water in step b of the method of the present invention, the oil-containing phospholipid composition is heated to a temperature of up to 90°C, more preferably up to 80°C, and most preferably up to 70°C. Preferably, the temperature of the composition before mixing with water is at least 30°C, more preferably at least 40°C, and most preferably at least 50°C.

[0028] Preferably, in step b of the method of the present invention, the temperature of the water mixed with the oil-containing phospholipid composition is at most 95°C, more preferably at most 85°C, and most preferably at most 75°C. Preferably, the water temperature of the oil composition before mixing is at least 30°C, more preferably at least 40°C, and most preferably at least 50°C.

[0029] Known devices, such as static or dynamic mixers, can be used to mix the water with the oil-containing phospholipid composition. Preferably, the mixing is carried out with stirring at a speed of up to 10,000 rpm, more preferably up to 5,000 rpm, and more preferably up to 1,000 rpm. Preferably, the stirring speed is at least 100 rpm, more preferably at least 200 rpm, and most preferably at least 300 rpm.

[0030] Preferably, mixing is carried out under stirring at a speed between 100 rpm and 10,000 rpm, the water temperature is between 30°C and 95°C, and the temperature of the oil-containing phospholipid composition is between 30°C and 90°C. It is anticipated that during certain stirring conditions (e.g., high stirring speeds), a portion of the stirring energy can be converted into heat, thus increasing the temperature of the aqueous solution. Preferably, the aqueous composition has a temperature of up to 90°C, more preferably up to 85°C, and most preferably up to 80°C. Preferably, the aqueous composition has a temperature of at least 40°C, more preferably at least 50°C, and most preferably at least 60°C.

[0031] The aqueous composition preferably has a pH of at least 5.0, more preferably at least 5.5, and most preferably at least 6.0. Preferably, the pH of the aqueous composition is at most 8.5, more preferably at most 8.0, and most preferably at most 7.5. Preferably, the pH is between 5.0% and 8.5, more preferably between 5.5 and 8.0, and most preferably between 6.0 and 7.5. The pH of the aqueous composition can be adjusted in well-known ways, for example by adding a base (or alkali), preferably a food-grade alkali, or by using a pH buffer. A buffer solution (more precisely, a pH buffer or hydrogen ion buffer) is an aqueous solution consisting of a mixture of a weak acid and its conjugate base, and vice versa. When a small amount of a strong acid or base is added to it, its pH changes very little. Buffer solutions are used as a way to maintain the pH at a nearly constant value in various applications, such as food, personal care, and pharmaceutical applications. Preferably, a food-grade alkali is used to adjust the pH of the aqueous environment. Non-limiting examples include ammonium hydroxide or ammonia, sodium hydroxide, sodium bicarbonate, potassium hydroxide, potassium carbonate and calcium hydroxide, quicklime / calcium oxide, calcium carbonate, and mixtures thereof. The pH can be measured using any pH meter known in the art, after it has been calibrated (if necessary) and used as shown in the operating instructions.

[0032] The term "aqueous composition" herein refers to a liquid composition containing water, and non-limiting examples include pure water (e.g., reverse osmosis water), aqueous solutions, and aqueous suspensions. In the context of this invention, the preferred aqueous environment is purified water or tap water. Preferably, based on the total weight of the composition, the aqueous composition contains at least 30% by weight of water, more preferably at least 40% by weight of water, even more preferably at least 50% by weight of water, even more preferably at least 60% by weight of water, even more preferably at least 70% by weight of water, even more preferably at least 80% by weight of water, and most preferably at least 90% by weight of water. Up to 100% of the remaining weight may contain additives; preservatives; vitamins; sterols, such as phytosterols; antioxidants, such as polyphenols; minerals beneficial to human nutrition; whole plant extracts; cellulose, such as microfibrillated cellulose and cellulose gels; dextrins; maltodextrins; sugars, such as sucrose and glucose; polyols, such as mannitol, erythritol, glycerol, sorbitol, xylitol, and maltitol; proteins or protein hydrolysates, such as plant or vegetable proteins and dairy proteins; oils and fats; surfactants; lecithin; glucomannans and / or galactomannans, such as guar gum, xanthan gum, locust bean gum, cinnamon gum, tara gum, konjac gum, alginates, agar, gellan gum, carrageenan, and β1,3-glucan; native starch; modified starch; and combinations thereof.

[0033] The aqueous composition is then separated into an oil-rich fraction and an oil-lean fraction. The oil-lean fraction contains water, phospholipids, and may also contain residual oil. The final composition of the oil-lean fraction depends on the crude oil used according to the invention and may contain particularly small amounts of waxes, gums, glucosides, etc.

[0034] The inventors have observed that the initial steps of the method of the present invention (i.e., the steps prior to the separation step) favor the separation step because the amount of oil in the lean fraction is at most 10% by weight, more preferably at most 9% by weight, and most preferably at most 8% by weight, relative to the mass of the fraction. Preferably, the separation step is carried out at a temperature of at most 90°C, more preferably at most 85°C, and most preferably at most 80°C (i.e., the temperature of the aqueous composition). Preferably, the temperature of the aqueous composition is at least 5°C, more preferably at least 15°C, and most preferably at least 30°C. Suitably, the temperature of the aqueous composition is regulated or maintained by passing through a heat exchanger, such as a plate heat exchanger or a tubular heat exchanger, or by using microwave heating.

[0035] Preferably, the separation step is carried out for about 1 hour to about 120 hours to ensure effective separation of the oil-rich phase and the oil-lean fraction. Therefore, it is possible, and most preferably, to separate the aqueous composition into an oil-rich phase and an oil-lean fraction in the absence of organic solvents.

[0036] Preferably, the aqueous composition is separated into an oil-rich phase and an oil-lean fraction by centrifugation. Alternatively, sedimentation may be used.

[0037] In a centrifuge, the liquids are separated into two phases of different densities, which flow out of the centrifuge through drain pipes. The centrifuge used is preferably a separator (vertical or horizontal) with a rotating axis, designed to separate two liquid phases of different densities. Preferably, the separation is carried out by centrifugation under a separation force of at least 1500 G, more preferably at least 3000 G, and most preferably at least 5000 G. Preferably, the centrifugation is carried out for at least 5 minutes, more preferably at least 15 minutes, and most preferably at least 30 minutes. Preferably, the aqueous composition during the centrifugation step has a temperature of at most 60°C, more preferably at most 55°C, and most preferably at most 50°C. Preferably, the temperature is at least 5°C, more preferably at least 15°C, and most preferably at least 25°C.

[0038] Preferably, the lean oil fraction is dried, for example, freeze-dried or vacuum-dried, to a moisture content of up to 5.0% by weight, more preferably up to 2.0% by weight, and most preferably up to 1.0% by weight. Preferably, the moisture content is at least 0.1% by weight, more preferably at least 0.3% by weight, and most preferably at least 0.5% by weight. The dried lean oil fraction can be ground into powder, as such powdered lean oil fraction is easier to handle and more economical to transport.

[0039] It is anticipated that after the initial steps of the method (e.g., steps a. to d.), the lean oil fraction may still contain more oil than desired (e.g., between 20% and 40% by weight). This may be the case when the oleophospholipid composition used as a starting or input material for the method of the present invention contains a large amount of oil, for example, more than 30% by weight. In this case, the method of the present invention may be applied to the lean oil fraction multiple times, for example, at least once more, more preferably at least twice, in order to further reduce the oil content of the lean oil fraction, preferably to less than 10% by weight, more preferably to at most 9% by weight, and most preferably to at most 8% by weight.

[0040] Preferably, steps c)-d) are repeated at least once more, that is, the lean fraction obtained in step d) is processed again by the method according to the invention, i.e., it is separated into the specified fraction in step c) and the rich fraction in step d) is removed. Preferably, steps c)-d) are repeated at least twice, and most preferably at least three times.

[0041] The present invention also relates to a water-de-oiled phospholipid composition (hereinafter referred to as the composition of the present invention for simplicity) comprising water, phospholipids and oil, said composition having at least 85% by weight, preferably at least 87% by weight, more preferably at least 89% by weight, more preferably at least 90.0% by weight, more preferably at least 91.0% by weight, more preferably at least 92.0% by weight, and most preferably at least 94.0% by weight of AI, the weight percentage being expressed relative to the total weight of said composition.

[0042] Preferably, the composition of the present invention comprises at most 10% by weight of oil, at most 5% by weight of water, and at least 85.0% by weight of Al. Preferably, the amount of oil is at most 9.0% by weight, more preferably at most 8.0% by weight, more preferably at most 7.0% by weight, more preferably at most 6.0% by weight, more preferably at most 5.0% by weight, more preferably at most 4.0% by weight, and most preferably at most 3.0% by weight. Preferably, the amount of oil is at least 0.1% by weight, more preferably at least 0.5% by weight, and most preferably at least 1.0% by weight. Preferably, the amount of water is 5.0% by weight, more preferably at most 4.0% by weight, more preferably at most 3.0% by weight, more preferably at most 2.0% by weight, and most preferably at most 1.0% by weight. Preferably, the amount of water is at least 0.1% by weight, more preferably at least 0.3% by weight, and most preferably at least 0.5% by weight. Preferably, the AI ​​is at least 87% by weight, more preferably at least 89% by weight, more preferably at least 90.0% by weight, more preferably at least 91.0% by weight, more preferably at least 92.0% by weight, and most preferably at least 94.0% by weight. Preferably, relative to the total weight of the composition, the AI ​​is at least 87% by weight, more preferably at least 89% by weight, more preferably at least 90.0% by weight, more preferably at least 91.0% by weight, more preferably at least 92.0% by weight, and most preferably at least 94.0% by weight, and the amount of combined oil and water is at most 10.0% by weight, more preferably at most 8.0% by weight, and most preferably at most 6.0% by weight.

[0043] The composition of the present invention preferably has at least 89% by weight of AI, wherein the amount of oil is at most 9.0% by weight, and the amount of water is at most 2% by weight. Preferably, the amount of oil is at most 8.0% by weight, more preferably at most 7.0% by weight, more preferably at most 6.0% by weight, more preferably at most 5.0% by weight, more preferably at most 4.0% by weight, and most preferably at most 3.0% by weight.

[0044] The composition of the present invention preferably has at least 90% by weight of AI, wherein the amount of oil is at most 8.0% by weight, and the amount of water is at most 2% by weight. Preferably, the amount of oil is at most 7.0% by weight, more preferably at most 6.0% by weight, more preferably at most 5.0% by weight, more preferably at most 4.0% by weight, and most preferably at most 3.0% by weight.

[0045] The composition of the present invention preferably has at least 91% by weight of AI, wherein the amount of oil is at most 7.0% by weight, and the amount of water is at most 2% by weight. Preferably, the amount of oil is at most 6.0% by weight, more preferably at most 5.0% by weight, more preferably at most 4.0% by weight, and most preferably at most 3.0% by weight.

[0046] The composition of the present invention preferably has at least 92% by weight of AI, wherein the amount of oil is at most 6.0% by weight, and the amount of water is at most 2% by weight. Preferably, the amount of oil is at most 5.0% by weight, more preferably at most 4.0% by weight, and most preferably at most 3.0% by weight.

[0047] The composition of the present invention preferably has at least 93% by weight of AI, wherein the amount of oil is at most 5.0% by weight, and the amount of water is at most 2.0% by weight. Preferably, the amount of oil is at most 3.0% by weight.

[0048] Preferably, the composition of the present invention is obtained by using a water-based deoiling method, i.e., a water-deoiled phospholipid composition. Preferably, the composition of the present invention is obtained by the method of the present invention. The water-deoiled phospholipid composition is characterized by containing tocopherol, a compound that is typically absent or present in very low amounts when deoiled using organic solvents. Preferably, the deoiled phospholipid composition contains at least 0.01% by weight of tocopherol relative to the total weight of the composition, more preferably at least 0.03% by weight, and most preferably at least 0.05% by weight. Additionally, the water-deoiled phospholipid composition may also contain zeaxanthin and / or lutein, which are carotenoids and whose antioxidant properties are known. These carotenoids are preferably present in amounts between 0.10 mg / 100 g of the water-deoiled phospholipid composition and 0.25 mg / 100 g of the water-deoiled phospholipid composition, while being practically absent in solvent-deoiled phospholipid compositions.

[0049] The present invention also relates to a food or feed product comprising the composition of the present invention and nutrients.

[0050] The compositions of this invention are highly suitable for producing a wide variety of food products. Examples of food products (containing or manufactured using the compositions of this invention) also covered by this invention include: trendy beverages such as coffee, black tea, green tea powder, cocoa, red bean soup, fruit juice, soy milk, etc.; dairy-containing beverages such as raw milk, processed milk, lactic acid drinks, etc.; various beverages, including nutrient-rich beverages such as calcium-fortified beverages and beverages containing dietary fiber, etc.; dairy products such as butter, cheese, yogurt, coffee brighteners, whipped cream, milk cake cream, milk pudding, etc.; frozen products such as ice cream, soft cream, milk ice, frozen milk, frozen fruit syrup, frozen yogurt, etc.; processed fatty food products such as mayonnaise, margarine, spreads, shortening, etc.; soups; stews; condiments such as sauces, tARE (seasoning sauces). Seasonings, etc.; various paste-like condiments, represented by kneaded mustard; various fillers, typically jams and flour pastes; various gel or paste-like food products, including red bean paste, jelly, and foods for people with impaired swallowing; food products containing grains as a main component, such as bread, noodles, pasta, pizza, tortilla chips, etc.; Japanese, American, and European pastries, such as candy, cookies, biscuits, muffins, chocolate, rice cakes, etc.; kneaded seafood products, represented by boiled fish cakes, fish cakes, etc.; livestock products, represented by ham, sausages, hamburgers, steaks, etc.; everyday meals, such as cream croquettes, Chinese porridge, creamed roasted vegetables, dumplings, etc.; umami foods, such as salted fish sausages, sake-pickled vegetables, etc.; liquid diets, such as tube-fed liquid foods, etc.; supplements; and pet food. Regardless of any differences in the form and processing methods of the food products during preparation, such as those seen in steamed, boiled, frozen, microwaved, etc., all these food products are covered within the scope of this invention.

[0051] The present invention also relates to a cocoa-based composition comprising the water-de-oiled phospholipid composition of the present invention and cocoa protein, wherein the amount of the phospholipid composition is between 0.05% by weight and 5.0% by weight, preferably between 0.1% by weight and 1.0% by weight, relative to the weight of the cocoa-based composition. The cocoa-based composition may also contain cocoa butter. Cocoa protein is typically obtained by grinding cocoa beans.

[0052] This invention also relates to a product comprising the composition of the invention and a surfactant system. Preferably, the amount of the surfactant system relative to the weight of the product is from 0.1% to 50% by weight, more preferably from 5% to 30% by weight, and even more preferably from 10% to 25% by weight. Generally, the surfactant may be selected from surfactants described in well-known textbooks, such as: “Surface Active Agents,” Volume 1, Schwartz & Perry, Interscience 1949, Volume 2, Schwartz, Perry & Berch, Interscience 1958, and / or the current edition of “McCutcheon's Emulsifiers and Detergents,” published by Manufacturing Confectioners Company, or “Tenside-Taschenbuch,” H. Stache, 2nd edition, Carl Hauser Verlag, 1981; “Handbook of Industrial Surfactants” (4th edition), Michael Ash and Irene Ash; Synapse Information Resources, 2008. The type of surfactant selected may depend on the intended application of the product. A surfactant system may comprise one type of surfactant, or a mixture of two or more surfactants. The synthetic surfactant preferably forms the main component of the surfactant system. Therefore, the surfactant system preferably comprises one or more surfactants selected from one or more of the following: anionic surfactants, cationic surfactants, nonionic surfactants, amphoteric surfactants, and zwitterionic surfactants. More preferably, one or more detergent surfactants are combinations of anionic surfactants, nonionic surfactants, or anionic and nonionic surfactants. Mixtures of synthetic anionic and nonionic surfactants, or entirely anionic mixed surfactant systems, or mixtures of anionic surfactants, nonionic surfactants, and amphoteric or zwitterionic surfactants may be used entirely according to the formulation personnel's selection for the desired cleaning purpose and the required dosage of the cleaning composition. Preferably, the surfactant system comprises one or more anionic surfactants. More preferably, the surfactant system comprises one or more anionic surfactants selected from lauryl ether sulfates and linear alkylbenzene sulfonates.

[0053] For certain applications, products containing a surfactant system preferably also contain 1% to 8% by weight of an inorganic salt, preferably selected from sulfates and carbonates, more preferably selected from MgSO4 and Na2SO4, and even more preferably MgSO4. Preferably, the product containing the surfactant system is a cleaning composition, more preferably a hand-washing dishwashing composition. The product may also include suspended particles and / or bubbles.

[0054] This invention also relates to cosmetic products comprising the compositions of this invention. Cosmetic products, as used herein, are understood, for example, as products used to enhance the appearance or odor of a human or animal body. In addition to the compositions of this invention, cosmetic products may also include any other cosmetic ingredients, such as any ingredients commonly used in formulations of said cosmetic products. Examples of cosmetic products include skin care creams, lotions, perfumes, lipsticks, nail polish and toenail polish, facial cosmetics, hair dyes and hairsprays, moisturizers, gels, deodorants, hand sanitizers, baby products, bath oils, bubble baths, butters, etc. The cosmetic products of this invention can be in any form or shape, such as liquids or creams / lotions.

[0055] This invention also relates to a pharmaceutical product comprising the composition of this invention and a drug or drug release agent. A drug, as understood herein, is a substance intended for the diagnosis, cure, relief, treatment, or prevention of disease. Drugs may be derived from natural sources, such as animal, microbial, or plant sources; chemical sources, i.e., derived from chemical synthesis; or combinations thereof.

[0056] Any feature of a specific embodiment of the invention may also be used in any other embodiment of the invention. The word “comprising” is intended to mean “including” but not necessarily “consisting of” or “made up of”. In other words, the listed steps or options are not necessarily exhaustive. It should be noted that the examples given in the following description are intended to illustrate the invention and are not intended to limit the invention to these examples alone. Similarly, unless otherwise specified, all percentages are weight / weight percentages. Except in the examples and comparative experiments, or where otherwise expressly indicated, all figures indicating the amount of material or reaction conditions, physical properties of the material and / or uses in this specification should be understood to be modified by the word “about”. Unless otherwise specified, numerical ranges expressed in the format “x to y” should be understood to include both x and y. When multiple preferred ranges are described in the format “x to y” for a particular feature, it should be understood that all ranges combining different endpoints may also be conceived. For the purposes of this invention, ambient temperature (or room temperature) is defined as a temperature of about 20 degrees Celsius.

[0057] Measurement methods

[0058] ● RO waterThis refers to reverse osmosis (RO) low conductivity water (milli-Q Ultrapure Millipore).

[0059] 18.2 MΩ·cm

[0060] ● Acetone insoluble matter (AI) is determined according to Lange R., Fiemon HJ (1999): Separation of Phospholipids, Standard Methods of DGF, Fett / Lipid 101:77-79. This method is based on the solubility of lecithin components (such as triglycerides, fatty acids, sterols, and other acetone-soluble components) and the insolubility of phospholipids and glycophospholipids in acetone under the test conditions. The latter is referred to as acetone-insoluble matter (AI). AI can also be determined according to AACC International Method 58-35.01 – “Acetone-Insoluble Lecithin”, however, the former method is preferred.

[0061] ● Moisture Content (“MC”): The moisture content of the sample is determined by weighing the sample, placing it in a pre-dried container, and then heating the container containing the sample in an oven at 105°C overnight. The moisture content (in weight %) is calculated as MC = (A1 - A2) / A1 × 100, where A1 is the weight of the sample before drying in the oven and A2 is the weight of the resulting dried sample.

[0062] ● Dry matter content ("DS") Measured according to the following formula: DS(%) = 100% - MC(%).

[0063] ● Phospholipid composition The phospholipid composition, namely the amounts of PC, PA, PI, and PE and their hydrolyzed fractions, is determined using liquid chromatography applied to the emulsifier composition, wherein the AI ​​of the emulsifier composition is set to 60% relative to the total weight of the emulsifier composition. The AI ​​amount can be adjusted by adding (or, for example, extracting with acetone) the necessary amount of the acetone-soluble fraction of the composition (primarily triglycerides) to achieve an AI amount of 60%. The identification and quantification of various phospholipid components can be conveniently performed using various methods, including thin-layer chromatography (TLC), high-performance liquid chromatography (HPLC), and methods specifically for phospholipids. 31 P nuclear magnetic resonance spectroscopy (P nuclear magnetic resonance spectroscopy) 31 Suitable methods are disclosed in the following literature: London E., Feigenson G.W. (1979): Phosphorous NMR Analysis of Phospholipids in Detergents, J.LipidRes. 20:408-412;

[0064] Aitzetmüller K. (1984): HPLC and Phospholipids, Part I: General Considerations, Fette, Seifen, Anstrichm.86:318-322; and Aloisi J.D., ShermaJ., Fried B. (1990): Comparison of Mobile Phases for Separation and Quantification of Lipids by One-Dimensional TLC and Preadsorbent HighPerformance Silica Gel Plates, J. Liq. Chromatogr. 13:3949-3961.

[0065] ● Ionic strength (I) and pH adjustment The supporting dispersion liquid is standardized tap water with an ionic strength of 0.02 M (1.00 g / L NaCl and 0.155 g / L CaCl2·2H2O) prepared by reverse osmosis (RO) low conductivity water (milli-QUltrapure Millipore 18.2 MΩ·cm). The pH is adjusted with 1 M NaOH, and the ionic strength is adjusted by adding the required mass of salt, NaCl, or CaCl2·2H2O. The ionic strength I (in molar concentration M) of the solution is determined according to the following formula:

[0066] I = 0.5([A]Z A 2 +[B]Z B 2 +[C]Z C 2 +…)

[0067] Where [A], [B], and [C] represent the molar concentrations of ions A, B, and C, and Z represents the concentration of ions Z. A Z B Z C Let these be their respective charges. See Skoog, West & Holler (1996).

[0068] Fundamentals of Analytical Chemistry, 7th Edition (Harcourt Brace&

[0069] Company, Orlando). In fact, for a [1:1] electrolyte (NaCl, NaOH)

[0070] For the [2:1] electrolyte (CaCl2), I = c (in terms of M), and for the [2:1] electrolyte (CaCl2), I = 3c.

[0071] The invention will now be described with the aid of the following embodiments and comparative experiments, but is not limited thereto.

[0072] Example 1 :

[0073] 225g of an oil-containing phospholipid composition (31% by weight of oil and 63.2% by weight of AI) obtained by degumming sunflower oil was preheated to 55°C and mixed with 75g of RO water at 55°C in a 3:1 ratio to form an aqueous composition. The aqueous composition was then heated to 70°C in a constant temperature bath, homogenized by stirring at 300 rpm (IKA stirring unit DW25, propeller stirrer diameter 5cm), and maintained at the stirring and set temperature for 1 hour.

[0074] One hour later, 4.53g of oil accumulated on the surface of the aqueous mixture was removed with a pipette.

[0075] The remaining aqueous composition was centrifuged twice (first and second times) in a Sigma 3K-15 centrifuge with rotor 11133, each time at 40°C and 5500 rpm for 1 hour. In both cases, the separated oil-rich fraction was removed. The oil-lean fraction, containing water, phospholipids, and residual oil (approximately 17 g), was frozen overnight at -20°C and then heated back to 40°C.

[0076] A certain amount of 0.7 g of RO water was added to the unfrozen, heated sample, and the sample was centrifuged again at 40 °C and 5500 rpm (a third centrifugation) for 1 hour. The resulting oil-rich fraction was separated. A total of 65 g of oil was removed from the sample.

[0077] The lean oil fraction containing 75g of water was freeze-dried (using a Zirbus Technologies Vac05 / Christ Alpha 2-4 with a corresponding metal plate) to a moisture content of 1.1% and then ground. The measured alkalinity (AI) was 91.1%.

[0078] Example 2

[0079] Example 1 was repeated, except that all centrifugation times were increased from 1 hour to 2 hours. The final AI after drying and grinding was 92.4%.

[0080] Example 3

[0081] Example 2 was repeated, except that the first centrifugation time was increased from 2 hours to 2.5 hours, while the other two centrifugation steps remained at 2 hours. The final AI after drying and grinding was 94.1%.

[0082] Example 4

[0083] Example 3 was repeated using a second batch of an oil-containing phospholipid composition comprising sunflower oil (33% oil, 63.3% AI, 44.5% phospholipids). The final AI after drying and milling was 91.7% and 94.1%.

[0084] Example 5

[0085] Example 1 was repeated, except that the total centrifugation time was increased to 6.5 hours (without any stops during the centrifugation step and without the addition of water), and the composition-to-water ratio was 1.5:1. The final AI after drying and grinding was 93.3%.

[0086] Comparative Experiment

[0087] Example 5 was repeated, except that a different composition-to-water ratio was used (Comparative Experiments A and B). Example 1 was repeated, except that a different composition-to-water ratio was used (Comparative Experiments C and D). Details are shown in Table 1.

[0088] Table 1

[0089] Comparative Experiment ratio AI (%) A 0.4:1 83.1 B 1:1 81.4 C 6.1:1 83.5 D 19:1 75.2

[0090] Example 6

[0091] The oil-containing phospholipid composition (36.5 wt% oil and 63.5 wt% AI) obtained by degumming sunflower oil was preheated to 55°C and mixed with RO water at 55°C to form an aqueous composition (see ratios in Table 2). The aqueous composition was heated to 70°C in a constant temperature bath, homogenized by stirring at 650 rpm (IKA stirring unit DW25, propeller stirrer diameter 5 cm), and held at the stirring and set temperature for 2 hours. Afterward, the oil accumulated on the surface of the aqueous mixture was removed by pipetting. The remaining aqueous composition was centrifuged (Sigma 3K-15 centrifuge with rotor 11133) for 1 hour at 35°C or 40°C and 5500 rpm. The separated oil-rich fraction was removed. The oil-lean fraction, containing water, phospholipids, and residual oil, was frozen overnight at -40°C or directly freeze-dried.

[0092] The water-containing lean oil fraction was freeze-dried (using a Zirbus Technologies Vac05 with a corresponding metal plate) to a water content of less than 1.5% and then ground. The measured AI content is shown in Table 2.

[0093] Table 2

[0094]

[0095] Example 7

[0096] The oil-containing phospholipid composition (oil content 36.2 wt% and AI 63.8 wt%) obtained by degumming raw sunflower oil was preheated to 55°C and mixed with RO water at 55°C to form an aqueous composition (see ratios in Table 3). The aqueous composition was then heated to 70°C in a constant temperature bath, homogenized by stirring at approximately 300 rpm (IKA stirring unit DW25, propeller stirrer diameter 5 cm), and maintained at the stirring and set temperature for 1 hour.

[0097] The aqueous composition was centrifuged (Sigma 3k-15 centrifuge with rotor 11133) for 6.5 hours at 40°C and 5500 rpm (see Table 3). After freezing the sample to -20°C overnight, the separated oil-rich fraction was removed directly with a pipette or by means of a scraper or spoon. The oil-lean fraction containing water, phospholipids, and residual oil was frozen overnight at -40°C or -20°C or directly freeze-dried.

[0098] The water-containing lean oil fraction was freeze-dried (using a Zirbus Technologies Vac05 / Christ Epsilon 2-4LSCplus with the corresponding metal plate or in a container) until the water content was less than 1.5% and then ground. AI is shown in Table 3.

[0099] Table 3

[0100]

[0101] Example 9

[0102] The lean fraction from Example 4 was used in a chocolate formulation as follows: a dark chocolate sample was melted for 24 hours, and then the fraction was added at 45°C in an amount between 0.1% and 0.7% by weight, and mixed for 15 minutes using an IKA mixer operating at 350 rpm. After mixing, the mixture was transferred to a pot and allowed to crystallize.

[0103] The yield stress of the chocolate samples was measured as follows: the samples were melted at 45°C for 24 hours and then stirred at 300 rpm for 90 seconds using an IKA stirrer. Measurements were performed using an Anton Paar rheometer (MCR 51) according to the IOCC 2000 method. Yield stress values ​​were calculated using the Casson method. All measurements were performed in duplicate.

[0104] As described above, comparative experiments were conducted; however, lecithin deoiled using commercial acetone (derived from Cargill's) was used. () replaces the aforementioned classification.

[0105] Experiments show that the yield stress values ​​of samples having the water-de-oiled composition of the present invention are almost similar to those achieved using commercial lecithin.

Claims

1. A method for extracting oil from an oil-containing phospholipid composition, the method comprising the following steps: (a) Provides an oil-containing phospholipid composition comprising phospholipids and oil, wherein the amount of oil is between 20% by weight and 80% by weight relative to the total weight of the oil-containing phospholipid composition; (b) Mixing water with the oil-containing phospholipid composition to obtain an aqueous composition, wherein the weight ratio of the oil-containing phospholipid composition to water is between 6.0:1.0 and 1.3:1.0; (c) Separating the aqueous composition into an oil-rich fraction and an oil-lean fraction, the oil-lean fraction comprising water and phospholipids; and (d) Remove the separated oil-rich fraction to obtain a water-containing oil-poor fraction containing phospholipids; (e) Optionally, the aqueous lean oil fraction is dried to obtain a dried lean oil fraction containing phospholipids. The aqueous composition therein has a pH range between 5.0 and 8.

5.

2. The method according to claim 1, wherein the amount of oil contained in the oil-containing phospholipid composition is between 40% by weight and 78% by weight.

3. The method according to claim 1, wherein the amount of oil contained in the oil-containing phospholipid composition is between 50% by weight and 76% by weight.

4. The method according to claim 1, wherein the amount of oil contained in the oil-containing phospholipid composition is between 60% by weight and 75% by weight.

5. The method according to claim 1, wherein the oil-containing phospholipid composition is obtained by degumming crude oil.

6. The method according to claim 5, wherein the crude oil is a vegetable oil, and the vegetable oil is selected from the following oils: acai oil, prickly palm oil, almond oil, babassu oil, blackcurrant seed oil, borage seed oil, rapeseed oil, cashew oil, coconut oil, coriander oil, corn oil, cottonseed oil, sea buckthorn seed oil, flaxseed oil, grapeseed oil, hazelnut oil, jojoba oil, macadamia nut oil, mango kernel oil, oxalis oil, mustard oil, cow's hoof oil, olive oil, palm oil, palm kernel oil, peanut oil, pecan oil, pine nut oil, pistachio oil, rice germ oil, safflower oil, camellia oil, sesame oil, shea butter, soybean oil, sunflower oil, ailanthus oil, walnut oil, and mixtures of the foregoing oils.

7. The method of claim 6, wherein the palm oil is palm oil extract.

8. The method of claim 5, wherein the crude oil is a vegetable oil, and the vegetable oil is selected from nut oils.

9. The method of claim 5, wherein the crude oil is a vegetable oil, and the vegetable oil is selected from natural-grade oils having a fatty acid composition improved by genetically modified organisms or conventional breeding.

10. The method of claim 1, wherein the oil-containing phospholipid composition contains phospholipids in an amount of at least 20 wt% relative to the weight of the composition.

11. The method of claim 1, wherein the oil-containing phospholipid composition contains phospholipids in an amount of at least 40% by weight relative to the weight of the composition.

12. The method of claim 1, wherein the oil-containing phospholipid composition contains phospholipids in an amount of at least 60% by weight relative to the weight of the composition.

13. The method according to claim 1, wherein in step (b), the weight ratio of the oil-containing phospholipid composition to water is between 5.0:1.0 and 1.5:1.

0.

14. The method according to claim 1, wherein in step (b), the weight ratio of the oil-containing phospholipid composition to water is between 4.0:1.0 and 2.0:1.

0.

15. The method according to claim 1, wherein in step (b), the weight ratio of the oil-containing phospholipid composition to water is between 3.5:1.0 and 2.5:1.

0.

16. The method of claim 1, wherein the oil-containing phospholipid composition is heated to up to 90°C before mixing the water in step b.

17. The method of claim 1, wherein the oil-containing phospholipid composition is heated to up to 80°C before mixing the water in step b.

18. The method of claim 1, wherein the oil-containing phospholipid composition is heated to a temperature of up to 70°C before mixing the water in step b.

19. The method according to claim 1, wherein the temperature of the water mixed with the oil-containing phospholipid composition in step b is at most 95°C.

20. The method of claim 1, wherein the temperature of the water mixed with the oil-containing phospholipid composition in step b is at most 85°C.

21. The method according to claim 1, wherein the temperature of the water mixed with the oil-containing phospholipid composition in step b is at most 75°C.

22. The method of claim 1, wherein the separation step is performed for 1 hour to 120 hours.

23. The method of claim 1, wherein the separation of the aqueous composition into the oil-rich fraction and the oil-lean fraction is performed by centrifugation.

24. The method of claim 1, wherein the lean oil fraction is dried to a water content of up to 5.0% by weight.

25. The method of claim 1, wherein the lean oil fraction is dried to a water content of at most 2.0% by weight.

26. The method of claim 1, wherein the lean oil fraction is dried to a water content of at most 1.0 wt%.

27. The method of claim 24, wherein the drying is freeze drying or vacuum drying.

28. The method according to any one of the preceding claims, wherein steps c)-d) are repeated at least once more.

29. A deoiled phospholipid composition, said deoiled phospholipid composition being obtained using the method of any one of the preceding claims, said deoiled phospholipid composition comprising water, phospholipids and oil, wherein the amount of oil is at most 10% by weight, the amount of water is at most 5% by weight and has at least 85.0% by weight of acetone insoluble matter, said weight percentage being expressed relative to the total weight of the composition, wherein said composition contains at least 0.01% by weight of tocopherol relative to the total weight of the composition.

30. The deoiled phospholipid composition of claim 29, wherein the composition contains at least 0.03% by weight of tocopherol relative to the total weight of the composition.

31. The deoiled phospholipid composition according to claim 29, wherein the composition contains at least 0.05% by weight of tocopherol relative to the total weight of the composition.

32. A food product comprising the composition and nutrients according to any one of claims 29-31.

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