Process for making oil-free compositions containing phospholipids

Abstract

The present invention relates to a method for extracting oil from an oil-containing phospholipid composition, comprising: (a) providing an oil-containing phospholipid composition, the composition comprising phospholipids and oil, the oil being in an amount of 80% by weight based on the total weight of the oil composition; (b) mixing water with the oil-containing phospholipid composition to obtain an aqueous composition, the weight ratio of the composition to water being 6.0:1.0 to 1.3:1.0; (c) separating the aqueous composition into an oil-enriched fraction and an oil-depleted fraction, the oil-depleted fraction comprising water and phospholipids; (d) removing the separated oil-enriched fraction to obtain an aqueous oil-depleted fraction comprising phospholipids; and (e) optionally drying the aqueous oil-depleted fraction to obtain a dried oil-depleted fraction comprising phospholipids.

Description

[Technical Field]

[0001] The present invention relates to a method for extracting oil from an oil composition comprising phospholipids. The present invention further relates to oil-free compositions comprising phospholipids obtained by the method of the present invention and their use in foods, beverages, nutritional products, dietary supplements, feeds, personal care applications, pharmaceutical applications, and industrial applications. [Background technology]

[0002] Phospholipid-containing plant compositions are by-products of oil production.As natural emulsifiers with excellent technical and nutritional physiological properties, these compositions are highly valuable in various industries, especially in the food industry.Today, more than 800 million people consume phospholipid-containing products every day.More and more synthetic emulsifiers and stabilizers are replacing them.

[0003] The demand for natural processed products, including those that contain phospholipids, is also increasing.In many food applications, there is a change towards using cleaner raw materials.In particular, the oil-free compositions that contain phospholipids are highly desirable due to their high emulsifying ability and excellent water dispersibility.Unfortunately, such oil-free compositions are typically produced using organic solvents, such as acetone, which is undesirable for certain products.Therefore, there is a need for cleaner oil-free compositions that contain phospholipids.

[0004] "Degumming" is the name given to a process in which, among other things, phospholipids are removed from a raw oil. A simple degumming process simply involves mixing water with oil and separating the resulting mixture into an oil component and an aqueous component containing, among other things, a portion of the phospholipids. An example of such a process is given in CA-A-522398, which describes a water degumming process for rice bran oil. Rice bran oil contains a high proportion of wax, and the process described in CA-A-522398 involves heating an oil / water mixture to hydrate the gums and then slowly cooling the mixture to allow the wax crystals to coalesce and separate with the aqueous component. Reheating the separated aqueous or sludge component is said to allow for the extraction of the wax as well as the entrained oil.

[0005] Another attempt to remove phospholipids from triglyceride oils is described in US-A-4162260, which proposes removing impurities from triglyceride oils by increasing the level of hydratable phosphatides before degumming.

[0006] However, there is a problem in known processes such as degumming process, because it is very difficult to extract most of the oil.Even when the process is repeated many times, a large amount of oil still exists in the composition that contains phospholipids.Therefore, there is a need for a process that can extract most of the oil content and provide the phospholipid composition that is essentially free of oil. Summary of the Invention [Means for solving the problem]

[0007] The present invention provides a method for extracting oil from an oil-containing phospholipid composition, comprising: a) providing an oil-containing phospholipid composition, the composition comprising phospholipids and oil, the oil being in an amount of 20 to 80 wt. % based on the total weight of the oil composition; b) mixing water with the oil-containing phospholipid composition to obtain an aqueous composition, wherein the weight ratio of the composition to water is 6.0:1.0 to 1.3:1.0; c) separating the aqueous composition into an oil-enriched fraction and an oil-depleted fraction, the oil-depleted fraction comprising water and phospholipids; d) removing the separated oil-enriched fraction to obtain an aqueous oil-depleted fraction comprising phospholipids; e) optionally drying the aqueous oil-depleted fraction to obtain a dry oil-depleted fraction comprising phospholipids.

[0008] The inventors have observed that the method according to the present invention (hereinafter "the method of the present invention") can produce an oil-depleted composition comprising phospholipids in an efficient and economical manner. Specifically, the oil-depleted composition obtained by the method of the present invention may contain some residual oil, in such small amounts that to the inventors' knowledge has not been achieved before.

[0009] Other advantages of the present invention will become apparent from the detailed description set forth below.

[0010] Detailed Description of the Invention The present invention relates to a method for extracting oil from a composition comprising phospholipids and oil (hereinafter the method of the invention).

[0011] The oil-containing phospholipid composition comprises phospholipids and oil, and the oil is present in an amount of 20 to 80% by weight based on the total weight of the oil composition. Preferably, the amount of oil contained in the composition is 25 to 75% by weight, and most preferably 30 to 70% by weight.

[0012] The oil-containing phospholipid composition can be obtained from a raw oil, for example, by degumming the raw oil. The raw oil can be obtained, for example, from plants, animals, algae, and / or microorganisms by pressing or extraction methods, for example, using organic solvents. Hot pressing and cold pressing methods are known for recovering raw oils. Extraction processes, such as hexane extraction, can also be used. However, various alternative measures are contemplated. As used herein, a raw oil does not necessarily have to be obtained directly from a living organism, but may have already been used for its intended purpose one or more times, such as in the case of frying oil or industrial oil. Specifically, as used herein, the term "raw oil" encompasses a composition of biological origin that can be obtained from plants, algae, animals, and / or microorganisms, and preferably has a water content of up to 10% by weight and at least 75% by weight of alkane and / or cyclic aromatic and / or mono-, di-, or triglyceride (acylglyceride) fractions based on the weight of the oil.

[0013] When the raw oil is obtained from algae, the algal oil is preferably selected from the group consisting of Neochloris oleoabundan oil, Scenedesmus dimorphus oil, Euglena gracilis oil, Phaeodactylum tricornutum oil, Pleurochrysis carterae oil, Prymnesium parvum oil, Tetraselmis chui oil, Tetraselmis suecica oil, Isochrysis galbana oil, Nannochloropsis salina oil, Botryococcus braunii oil, Dunaliella tertiolecta oil, Nannochloris oil, Spirulina oil, Chlorophyceae oil, Bacilliarophyta oil, or a mixture of the aforementioned oils.

[0014] Preferably, the raw oil is a vegetable oil, such as acai oil, acrocomia oil, almond oil, babassu oil, blackcurrant seed oil, borage seed oil, rapeseed oil, cashew oil, castoreum oil, coconut oil, coriander oil, corn oil, cottonseed oil, cranberry oil, linseed oil, grapeseed oil, hazelnut oil, other nut oils, hemp seed oil, potato coral oil, jojoba oil, macadamia nut oil, mango kernel oil, cardamom oil, mustard oil, ox foot oil, olive oil, palm oil, palm kernel oil, palm olein oil, peanut oil, pecan oil, pine kernel oil, pistachio oil, poppy oil, rice germ oil, safflower oil, camellia oil, sesame oil, shea butter oil, soybean oil, sunflower oil, tall oil, camellia oil, walnut oil, genetically modified organisms (GMOs). The oil is selected from the group consisting of "natural" grade oils having fatty acid compositions that have been modified through genetically modified organisms (GMOs) or traditional breeding, and mixtures of the aforementioned oils.

[0015] Most preferably, the raw oil is a vegetable oil selected from the group consisting of sunflower oil, safflower oil, canola oil, rapeseed oil, rice bran oil, olive oil, soybean oil, corn oil, cottonseed oil, sesame seed oil, palm olein, palm kernel olein, their corresponding high oleic varieties, and mixtures of two or more thereof. High oleic varieties are oils containing at least 40%, at least 50%, at least 60%, at least 70%, preferably at least 80% oleic acid based on their fatty acid profile. Particularly preferred liquid oils are sunflower oil, rapeseed oil, soybean oil, palm olein (mono- or bisected), and palm kernel oil.

[0016] The content of the oil-containing phospholipid composition used according to the present invention depends on the raw oil used as the source from which the composition is obtained. For purposes of the present invention, an oil composition contains phospholipids and 20-80% by weight of oil, where the oil is an oil naturally occurring in the raw oil. The oil composition may also contain waxes, gums, glucosides, and the like, as well as water. Preferably, the oil composition contains water in an amount of up to 50% by weight, more preferably up to 35% by weight, and most preferably up to 25% by weight, based on the weight of the composition, with the amount of oil in the composition being within the required 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.

[0017] The oil-containing phospholipid composition contains phospholipids. Depending on the raw oil, the nature and content of phospholipids in the oil composition may vary. Phospholipids (also called phosphatides) are phosphorus-containing organic substances with fatty properties. Phospholipids are classified into non-hydratable phospholipids (NHP) and hydratable phospholipids (HP). Examples of hydratable or partially hydratable phospholipids include phosphatidylinositol or its salt, phosphatidylcholine, and phosphatidylethanolamine. An example of a non-hydratable phospholipid is a salt of phosphatidic acid (e.g., its calcium or magnesium salt). Typical examples of cations of phospholipids include sodium, potassium, calcium, etc.

[0018] Preferably, the oil-containing phospholipid composition is obtained from the feedstock oil by a degumming operation. In this operation, water is typically added to the feedstock oil to precipitate phospholipids and facilitate their removal from the feedstock oil. If the phospholipids are hydratable, they are hydrated by adding water to the feedstock oil. The precipitated phospholipids can be separated from the oil using centrifugal force. Non-hydratable phospholipids can be converted to a hydratable form, for example, by adding an acid, and / or can be removed by filtration or using a solvent. Specifically, the addition of acid can include the addition of a dilute acid, or, equally preferably, the addition of a concentrated acid in conjunction with the subsequent addition of water. The addition of acid is called acid degumming, while the addition of water is known as water degumming. Preferably, acid degumming is carried out by dispersing an acid or anhydride having a pH of at least 0.5 as measured in a molar aqueous solution at 20°C in the feedstock, dispersing 0.2 to 5% water by weight of the feedstock in the mixture so obtained, and maintaining the resulting mixture at a temperature below 40°C for at least 5 minutes before separating it into oil and sludge fractions.

[0019] After degumming, (i) a degummed oil fraction is obtained, which, however, still has a residual fraction of phospholipids, mainly non-hydratable phospholipids, and (ii) a phospholipid-rich sludge fraction is obtained, containing mainly hydratable phospholipids, as well as oil and some water. The sludge fraction is used for the purposes of the present invention, and for convenience, is referred to herein as an oil-containing phospholipid composition. The degumming process can be easily and routinely carried out to provide an oil-containing phospholipid composition suitable for use in the present invention.

[0020] Preferably, the oil-containing phospholipid composition contains phospholipids in an amount of at least 20% by weight, more preferably at least 40% by weight, and most preferably at least 60% by weight, based on the weight of the composition (as measured by the Acetone Insoluble (AI) method presented in the Methods section), provided that the amount of oil in the composition is within the required range. The amount of phospholipids is preferably up to 75% by weight, more preferably up to 73% by weight, and most preferably up to 70% by weight. Those skilled in the art can easily adjust the AI ​​concentration by varying the parameters of the degumming process, such as the amount of water used for degumming (using lower amounts of water results in higher AI).

[0021] The method of the present invention further suggests a step in which water is mixed with the oil-containing phospholipid composition in a carefully selected ratio. The inventors have observed that oil extraction from the composition is enhanced when the weight ratio of the composition to water is between 6.0:1.0 and 1.3:1.0. 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, more preferably between 5.0:1.0 and 1.5:1.0, 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. Mixing water with the oil-containing phospholipid composition can be carried out by conventional means in the art, for example, using mixers such as static mixers, dynamic mixers, and high-shear mixers, and centrifugal pumps.

[0022] Preferably, the oil-containing phospholipid composition is heated to a temperature of at most 90°C, more preferably at most 80°C, most preferably at most 70°C, before mixing with water in step b of the method of the present invention. Preferably, the temperature of the composition before mixing with water is at least 30°C, more preferably at least 40°C, most preferably at least 50°C.

[0023] Preferably, the temperature of the water mixed with the oil-containing phospholipid composition in step b of the method of the present invention is at most 95° C., more preferably at most 85° C., most preferably at most 75° C. Preferably, the temperature of the water in the oil composition before mixing with the water is at least 30° C., more preferably at least 40° C., most preferably at least 50° C.

[0024] Water can be mixed with oil-containing phospholipid composition by known means, for example, using a static or dynamic mixer.Preferably, mixing is carried out under stirring with a speed of up to 10,000 rpm, preferably up to 5,000 rpm, more preferably up to 1,000 rpm.Preferably, the stirring speed is at least 100 rpm, more preferably at least 200 rpm, most preferably at least 300 rpm.

[0025] Preferably, the mixing is carried out with stirring at a speed of 100 to 10,000 rpm, the water having a temperature of 30 to 95°C, and the oil-containing phospholipid composition having a temperature of 30 to 90°C. It is contemplated that under certain stirring conditions, such as high stirring speeds, some of the stirring energy may be converted into heat, resulting in an increase in the temperature of the aqueous solution. Preferably, the aqueous composition has a temperature of at most 90°C, more preferably at most 85°C, and most preferably at most 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.

[0026] 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 5.0 to 8.5, more preferably 5.5 to 8.0, and most preferably 6.0 to 7.5. The pH of the aqueous composition can be adjusted by well-known means, such as by adding a base (or alkali), preferably a food-grade base, or by using a pH buffer. A buffer (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, or vice versa. When a small amount of a strong acid or base is added, the pH changes very little. Buffers are used in a wide variety of applications, such as food, personal care, and pharmaceutical applications, as a means of maintaining a nearly constant pH. Preferably, a food-grade base is utilized to adjust the pH of the aqueous environment, non-limiting examples of which include ammonium hydroxide or aqueous 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 with any pH meter known in the art after performing its calibration (if required) and using the pH as indicated in the operating instructions.

[0027] As used herein, an aqueous composition refers to a liquid composition containing water, non-limiting examples of which include pure water (e.g., reverse osmosis water), aqueous solutions, and water suspensions. Within the context of the present invention, a preferred aqueous environment is purified water or tap water. Preferably, the aqueous composition contains at least 30% by weight of water, more preferably at least 40% by weight, even more preferably at least 50% by weight, even more preferably at least 60% by weight, even more preferably at least 70% by weight, even more preferably at least 80% by weight, and most preferably at least 90% by weight of water, based on the total weight of the composition. The remaining weight percent up to 100% may include additives; preservatives; vitamins; sterols such as phytosterols; antioxidants such as polyphenols; beneficial minerals for human nutrition; whole plant extracts; celluloses such as microfibrillated cellulose and cellulose gels; dextrins; maltodextrins; sugars such as sucrose, glucose; polyols such as mannitol, erythritol, glycerol, sorbitol, xylitol, maltitol; proteins or protein hydrolysates such as plant or vegetable proteins and dairy proteins; oils and fats; surfactants; lecithin; guarmannans and / or galactomannans, such as guar gum, xanthan gum, locust bean gum, cassia gum, tara gum, konjac gum, alginates, agar, gellan gum, carrageenan and beta-1,3 glucan; native starches; modified starches; and combinations thereof.

[0028] The aqueous composition is then separated into an oil-enriched fraction and an oil-depleted fraction. The oil-depleted fraction contains water, phospholipids, and may also contain residual amounts of oil. The final composition of the oil-depleted fraction depends on the feedstock used according to the invention and may contain, inter alia, trace amounts of waxes, gums, glucosides, and the like.

[0029] The inventors have observed that the initial steps of the process of the invention (i.e., steps prior to the separation step) facilitate the separation step in which the amount of oil in the oil-depleted 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, i.e., a temperature of the aqueous composition of at most 90°C, more preferably at most 85°C, and most preferably at most 80°C. 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 adjusted or maintained by passing it through a heat exchanger, for example a plate or tube heat exchanger, or by the use of microwave heating.

[0030] Preferably, the separation step is carried out for about 1 hour to about 120 hours to allow the oil-rich phase to efficiently separate from the oil-depleted fraction. Thus, separation of the aqueous composition into an oil-rich phase and an oil-depleted fraction can be effected, most preferably in the absence of organic solvents.

[0031] Preferably, the separation of the aqueous composition into an oil-rich phase and an oil-depleted fraction is carried out using centrifugal force. Alternatively, sedimentation may be used.

[0032] In the centrifuge, the separation occurs in two phases with different densities, and these phases are discharged from the centrifuge through a drain. The centrifuge used is preferably a separator with a rotating shaft (which may be vertical or horizontal) designed to separate two liquid phases with different densities. Preferably, the separation is carried out using centrifugal force 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.

[0033] Preferably, the oil-depleted fraction is dried, e.g., freeze-dried or vacuum-dried, to a moisture content of at most 5.0 wt.%, more preferably at most 2.0 wt.%, and most preferably at most 1.0 wt.%. Preferably, the moisture content is at least 0.1 wt.%, more preferably at least 0.3 wt.%, and most preferably at least 0.5 wt.%. The dried oil-depleted fraction can be ground into a powder, as a powdered oil-depleted fraction is easier to handle and more economical to transport.

[0034] It is contemplated that after carrying out the initial steps of the process (e.g., steps a-d), the oil-depleted fraction may still contain oil in a greater amount than desired (e.g., 20-40% by weight). This may be the case when the oil-containing phospholipid composition used as the starting or input material in the method of the present invention contains a large amount of oil, e.g., more than 30% by weight. In this case, the method of the present invention can be applied to the oil-depleted fraction several times, e.g., at least once, more preferably at least twice, to reduce the amount of additional oil contained by the oil-depleted fraction, preferably to less than 10% by weight, more preferably to a maximum of 9% by weight, and most preferably to a maximum of 8% by weight.

[0035] Preferably, steps c) to d) are repeated at least once, i.e. the oil-depleted fraction obtained in step d) is again treated according to the process of the invention, i.e. separated into the fractions indicated in step c) and the oil-enriched fraction removed in step d). Preferably, steps c) to d) are repeated at least twice, most preferably at least three times.

[0036] The present invention further relates to a water-deoiled phospholipid composition (hereinafter for convenience referred to as the composition of the invention) comprising water, phospholipid, and oil, said composition having an AI of 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, wherein the weight percentages are expressed relative to the total weight of the composition.

[0037] Preferably, the composition of the present invention has an oil content of up to 10% by weight, a water content of up to 5% by weight, and an AI of at least 85% by weight. Preferably, the oil content is up to 9% by weight, more preferably up to 8% by weight, more preferably up to 7% by weight, more preferably up to 6% by weight, more preferably up to 5% by weight, more preferably up to 4% by weight, and most preferably up to 3% by weight. Preferably, the oil content is at least 0.1% by weight, more preferably at least 0.5% by weight, and most preferably at least 1% by weight. Preferably, the water content is 5% by weight, more preferably up to 4% by weight, more preferably up to 3% by weight, more preferably up to 2% by weight, and most preferably up to 1% by weight. Preferably, the water 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. 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, 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, based on the total weight of the composition, and the combined amount of 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.

[0038] The composition of the present invention preferably has an AI of at least 89% by weight, with the amount of oil being at most 9.0% by weight and the amount of water being at most 2% by weight. Preferably, the oil is present in an amount of 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.

[0039] The composition of the present invention preferably has an AI of at least 90% by weight, with the amount of oil being at most 8.0% by weight and the amount of water being at most 2% by weight. Preferably, the oil is present in an amount of 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.

[0040] The composition of the present invention preferably has an AI of at least 91% by weight, with an oil content of at most 7.0% by weight and a water content of at most 2% by weight. Preferably, the oil content 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.

[0041] The composition of the present invention preferably has an AI of at least 92% by weight, with an oil content of up to 6.0% by weight and water content of up to 2% by weight. Preferably, the oil content is up to 5.0% by weight, more preferably up to 4.0% by weight, and most preferably up to 3.0% by weight.

[0042] The composition of the present invention preferably has an AI of at least 93% by weight, with the amount of oil being at most 5.0% by weight and the amount of water being at most 2.0% by weight. Preferably, the amount of oil is at most 3.0% by weight.

[0043] Preferably, the inventive composition of the present invention is obtained by a de-oiling method using water, i.e., a water-de-oiled phospholipid composition. Preferably, the inventive composition is obtained by the method of the present invention. A characteristic of a water-de-oiled phospholipid composition is that it contains tocopherol, a compound that is typically absent or present in very low amounts when de-oiling is carried out using organic solvents. Preferably, the de-oiled phospholipid composition contains at least 0.01 wt. % tocopherol, more preferably at least 0.03 wt. %, and most preferably at least 0.05 wt. % of tocopherol, based on the total weight of the composition. Additionally, the water-de-oiled phospholipid composition can also contain zeaxanthin and / or lutein, which are carotenoids known for their antioxidant properties. These carotenoids are preferably present in an amount of 0.10 to 0.25 mg / 100 g of the water-de-oiled phospholipid composition, while being substantially absent in the solvent-de-oiled phospholipid composition.

[0044] The present invention further relates to food or feed products containing the compositions and nutrients of the present invention.

[0045] The composition of the present invention is very suitable for use in producing a wide variety of food products. Examples of foods that contain the composition of the present invention or are produced by using the composition of the present invention and to which the present invention also relates include various beverages, including high-quality beverages such as coffee, black tea, powdered green tea, cocoa, adzuki bean soup, juice, soybean juice, etc.; dairy beverages such as raw milk, processed milk, lactic acid beverages, calcium-fortified beverages, and the like, as well as nutritionally enriched beverages such as dietary fiber beverages; dairy products such as butter, cheese, yogurt, coffee creamer, whipped cream, custard cream, custard pudding, etc.; ice cream, soft serve ice cream, lacto ice cream, ice milk, sherbet, frozen yogurt, etc.; processed fatty foods such as mayonnaise, margarine, spreads, shortening, etc.; flavorings such as soups, stews, sauces, TARE (flavored sauces), dressings, etc. These include seasonings, various paste-like condiments such as kneaded mustard, various fillings characterized as jams and flour pastes, various gel- or paste-like foods including red bean jam, jelly, and foods for people with swallowing disabilities, foods containing grains as a main ingredient such as bread, noodles, pasta, pizza pie, and corn flakes, Japanese, American, and European cakes such as candy, cookies, biscuits, pancakes, chocolate, and mochi, seafood pastes such as boiled fish balls and fish balls, livestock products such as ham, sausages, and hamburger steaks, prepared dishes such as cream croquettes, pastes for Chinese cuisine, gratins, and dumplings, delicately flavored foods such as salted fish and vegetables pickled in sake lees, liquid foods such as liquid foods supplied in tubes, supplements, and pet foods. These foods are all encompassed within the scope of the present invention, regardless of their form or processing operation during preparation, as seen in retort pouch foods, frozen foods, and microwaveable foods.

[0046] The present invention also relates to a cocoa-based composition comprising the water-deoiled phospholipid composition of the present invention and cocoa mass, wherein the phospholipid composition is present in an amount of 0.05% to 5.0% by weight, preferably 0.1% to 1.0% by weight, based on the weight of the cocoa-based composition. The cocoa-based composition may also contain cocoa butter. The cocoa mass is typically obtained by crushing cocoa beans.

[0047] The present invention also relates to a product comprising the composition and surfactant system of the present invention. Preferably, the surfactant system is present in an amount of 0.1 to 50% by weight, more preferably 5 to 30% by weight, and even more preferably 10 to 25% by weight, based on the weight of the product. Generally, surfactants are selected from the group consisting of surfactants and surfactant-based surfactants, as described in "Surface Active Agents," Vol. 1, by Schwartz & Perry, Interscience 1949, Vol. 2, by Schwartz, Perry & Berch, Interscience 1958, and / or the current edition of "McCutcheon's Emulsifiers and Detergents," published by Manufacturing Confectioners Company, or "Tenside-Taschenbuch," by H. Stache, 2002. nd Edn., Carl Hauser Verlag, 1981, “Handbook of Industrial Surfactants” (4 thThe surfactants may be selected from surfactants described in well-known textbooks, such as "Surfactants for Cleaning, Washing, and Drying," by Michael Ash and Irene Ash, Synapse Information Resources, 2008. The type of surfactant selected may depend on the type of application for which the product is intended. The surfactant system may contain one type of surfactant or a mixture of two or more surfactants. Synthetic surfactants preferably form the majority of the surfactant system. Therefore, the surfactant system preferably contains one or more surfactants selected from one or more of anionic surfactants, cationic surfactants, nonionic surfactants, amphoteric surfactants, and zwitterionic surfactants. More preferably, the one or more detergent surfactants are anionic, nonionic, or a combination of anionic and nonionic surfactants. Mixtures of synthetic anionic and nonionic surfactants, or fully anionic mixed surfactant systems or mixtures of anionic surfactants, nonionic surfactants, and amphoteric or zwitterionic surfactants, may all be used according to the formulator's choice regarding the required cleaning duty and the required dosage of the cleaning composition. Preferably, the surfactant system contains one or more anionic surfactants. More preferably, the surfactant system comprises one or more anionic surfactants selected from the group consisting of lauryl ether sulfates and linear alkyl benzene sulfonates.

[0048] For specific applications, the product comprising the surfactant system also preferably comprises 1-8 wt. % of an inorganic salt, preferably selected from sulfates and carbonates, more preferably MgSO4 and Na2SO4, even more preferably MgSO4. Preferably, the product comprising the surfactant system is a cleaning composition, more preferably a hand dishwashing composition. The product may further comprise suspended particles and / or air bubbles.

[0049] The present invention further relates to a cosmetic comprising the composition of the present invention. Cosmetics are herein understood to mean products used, for example, to enhance the appearance or fragrance of the human or animal body. In addition to the composition of the present invention, the cosmetic may contain any additional cosmetic ingredients, for example, any ingredients commonly used in the formulation of such cosmetics. Examples of cosmetics include skin care cream lotions, fragrances, lipsticks, finger and toe nail polish, facial makeup, hair color and hair spray, moisturizers, gels, deodorants, hand sanitizers, baby products, bath additives, foam additives, butters, and the like. The cosmetic of the present invention may be in any form or shape, for example, a liquid or cream emulsion.

[0050] The present invention further relates to a pharmaceutical product comprising the composition of the present invention and a drug or drug-releasing agent. A drug is herein understood to be a substance intended for use in the diagnosis, cure, mitigation, treatment, or prevention of disease. The drug may be of natural origin, e.g., animal, microbial, or plant origin, or of chemical origin, i.e., chemical synthesis, or a combination thereof.

[0051] Any feature of a particular embodiment of the present invention may be utilized in any other embodiment of the present invention. The term "comprising" is intended to mean "including," but not necessarily "consisting of" or "composed of." In other words, the listed steps or options need not be exhaustive. It should be noted that the examples given in the following description are intended to clarify the invention and are not intended to limit the invention to those examples themselves. Similarly, unless otherwise indicated, all percentages are weight / weight percentages. Except in the examples and comparative experiments, or where otherwise explicitly stated, all numbers, materials, and / or physical properties in this description indicating amounts of materials or reaction conditions should be understood to be modified by the word "about." Unless otherwise specified, numerical ranges expressed in the format "x to y" are understood to include x and y. For a particular feature, when multiple preferred ranges are described in the format "x to y," it is understood that all ranges combining the different endpoints are also contemplated. For purposes of the present invention, ambient temperature (or room temperature) is defined as a temperature of about 20 degrees Celsius.

[0052] Measurement method RO water means reverse osmosis (RO) low conductivity water (milli-Q Ultrapure Millipore 18.2MΩ.cm). Acetone-insoluble matter (AI) was determined according to Lange R., Fiebig 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 called acetone-insoluble matter (AI). AI can also be determined according to AACC International Method 58-35.01 - "Acetone-Insoluble Lecithin," but the former method is preferred. Moisture content (MC): The moisture content of the sample was determined by weighing the sample, placing the sample in a pre-drying container, and then heating the container containing the sample in an oven at 105°C overnight. The moisture content (wt%) was calculated as MC = (A1 - A2) / A1 x 100, where A1 was the weight of the sample before drying in the oven and A2 was the weight of the resulting dried sample. Dry substance content (DS) is determined according to the formula: DS(%)=100%-MC(%). Phospholipid composition: The phospholipid composition, i.e., the amount of PC, PA, PI, and PE, as well as their hydrolyzed fractions, is determined using a liquid-chromatographic method and applied to an emulsifier composition with an AI set at 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 required amount of acetone-soluble parts (mainly triglycerides) of the composition to bring the AI ​​amount to 60%. The identification and quantification of the various phospholipid components can be performed using thin-layer chromatography (TLC), high performance liquid chromatography (HPLC), and, for phospholipids only, by HPLC. 31P nuclear magnetic resonance spectroscopy, 31 This can be conveniently done by different methods, including P-NMR. Suitable methods are disclosed in London E., Feigenson GW (1979): Phosphorous NMR Analysis of Phospholipids in Detergents, J. Lipid Res. 20:408-412, Aitzetmuller K. (1984): HPLC and Phospholipids, Part I: General Considerations, Fette, Seifen, Anstrichm. 86:318-322, and Aloisi JD, Sherma J., Fried B. (1990): Comparison of Mobile Phases for Separation and Quantification of Lipids by One-Dimensional TLC and Presorbent High Performance Silica Gel Plates, J. Liq. Chromatogr. 13:3949-3961. Ionic strength (I) and pH adjustment: The loading dispersion was standardized tap water (1.00 g / L NaCl and 0.155 g / L CaCl2.2H2O) with an ionic strength of 0.02 M, adjusted with reverse osmosis (RO) low-conductivity water (milli-Q Ultrapure Millipore 18.2 MΩ.cm). The pH was adjusted with 1 M NaOH, and the ionic strength was adjusted by spiking the required mass of salt, NaCl, or CaCl2.2H2O. The ionic strength I (in molarity M) of the solution was determined according to the following formula: I=0.5([A]Z A 2 +[B]Z B 2 +[C]Z C 2 +...) where [A], [B], and [C] are the molar concentrations of ions A, B, and C, and Z A , Z B , ZC are the respective charges. Skoog, West & Holler (1996). Fundamentals of Analytical Chemistry, 7 th See the "Immuno-Equivalents of Immuno-Equivalents" edition (Harcourt Brace & Company, Orlando). In fact, I = c (in M) for a [1:1] electrolyte (NaCl, NaOH), and I = 3c for a [2:1] electrolyte (CaCl).

[0053] The present invention will now be illustrated with the aid of the following examples and comparative experiments, but is not limited thereto.

[0054] Example 1: 225 gr of oil-containing phospholipid composition obtained by degumming raw sunflower oil, having an oil content of 31% by weight and an AI of 63.2% by weight, was preheated to 55° C. and mixed with 75 g of RO water having a temperature of 55° C. in a ratio of 3:1 to form an aqueous composition. The aqueous composition was heated to a maximum of 70° C. in a thermostatic bath and homogenized by stirring (IKA stirring unit DW25, propeller stirrer, diameter 5 cm) at 300 rpm, stirring and maintaining at the set temperature for 1 hour. After 1 hour, 4.53 g of oil that had accumulated on the surface of the aqueous mixture was removed with a pipette.

[0055] The remaining aqueous composition was centrifuged twice (first and second times) (Centrifuge Sigma 3K-15 with rotor 11133) for 1 hour each time at 40°C and 5500 rpm. In both cases, the separated oil-enriched fraction was removed. The oil-depleted fraction, containing water, phospholipids, and a residual amount of oil (approximately 17 g), was frozen overnight at -20°C and then reheated to 40°C.

[0056] An amount of 0.7 g of RO water was added to the unfrozen, heated sample, which was centrifuged again (third centrifugation) at 40°C and 5500 rpm for 1 hour. The obtained oil-enriched fraction was separated. A total of 65 g of oil was removed from the sample.

[0057] 75 g of the water-containing oil-depleted fraction was freeze-dried (Zirbus Technologies Vac05 / Christ Alpha 2-4 with corresponding metal plates) to a moisture content of 1.1% and ground. The AI ​​was determined to be 91.1%.

[0058] Example 2 Example 1 was repeated with the difference that all centrifugation times were increased from 1 hour to 2 hours. The final AI after drying and grinding was 92.4%.

[0059] Example 3 Example 2 was repeated with the difference that the first centrifugation time was increased from 2 hours to 2.5 hours, while the other two centrifugation steps were kept at 2 hours. The final AI after drying and grinding was 94.1%.

[0060] Example 4 Example 3 was repeated with a second batch of oil-containing phospholipid composition containing sunflower oil (33% oil, 63.3% AI, 44.5% phospholipids). The final AI after drying and milling was 91.7% and 94.1%.

[0061] Example 5 Example 1 was repeated with the difference that the complete centrifugation time was increased to 6.5 hours (without any stops and no water was added during the centrifugation step) and the composition to water ratio was 1.5: 1. The final AI after drying and grinding was 93.3%.

[0062] Comparative experiment Example 5 was repeated (Comparative Experiments A and B), with the difference being that different composition to water ratios were used. Example 1 was repeated (Comparative Experiments C and D), with the difference being that different composition to water ratios were used. Details are provided in Table 1.

[0063] [Table 1]

[0064] Example 6 An oil-containing phospholipid composition obtained by degumming raw sunflower oil, having an oil content of 36.5% by weight and an AI of 63.5% by weight, was preheated to 55°C and mixed with RO water having a temperature of 55°C to form an aqueous composition (see ratios in Table 2). The aqueous composition was heated to a maximum of 70°C in a thermostatic bath and homogenized by stirring at 650 rpm (IKA stirring unit DW25, propeller stirrer, 5 cm diameter), and maintained at the set temperature for 2 hours. After that time, the oil accumulated on the surface of the aqueous mixture was removed with a pipette. The remaining aqueous composition was centrifuged (Sigma 3K-15 Centrifuge with rotor 11133) at 35 or 40°C and 5500 rpm for 1 hour. The separated oil-enriched fraction was removed. The oil-depleted fraction, containing water, phospholipids, and a residual amount of oil, was either frozen overnight at -40°C or directly freeze-dried. The water-containing oil-depleted fraction was freeze-dried (Zirbus Technologies Vac05 with corresponding metal plates) to a moisture content of less than 1.5% and ground. The measured AI content is presented in Table 2.

[0065] [Table 2]

[0066] Example 7 An oil-containing phospholipid composition obtained by degumming raw sunflower oil, having an oil amount of 36.2 wt. % and an AI of 63.8 wt. %, was preheated to 55°C and mixed with RO water having a temperature of 55°C to form an aqueous composition (see ratios in Table 3). The aqueous composition was then heated to a maximum of 70°C in a thermostatic bath and homogenized by stirring (IKA stirring unit DW25, propeller stirrer, diameter 5 cm) at about 300 rpm, stirring and maintaining at the set temperature for 1 hour.

[0067] The aqueous composition was centrifuged (Centrifuge Sigma 3K-15 with rotor 11133) at 40° C. and 5500 rpm for 6.5 hours (see FIG. 3). The separated oil-enriched fraction was removed directly with a pipette or with the aid of a spatula or spoon after freezing the sample overnight at −20° C. The oil-depleted fraction, containing water, phospholipids, and residual amounts of oil, was either frozen overnight at −40° C. or −20° C. or directly freeze-dried.

[0068] The water-containing oil-depleted fraction was freeze-dried (Zirbus Technologies Vac05 / Christ Epsilon 2-4 LSCplus with corresponding metal plates or in a container) to a moisture content of less than 1.5% and ground. The AIs are presented in Table 3.

[0069] [Table 3]

[0070] Example 9 The oil-depleted fraction of Example 4 was used in a chocolate recipe as follows: a dark chocolate sample was melted for 24 hours, after which the fraction was added in an amount of 0.1-0.7% by weight at 45°C and blended for 15 minutes using an IKA stirrer operating at 350 rpm. After mixing, the mixture was transferred to a pot and allowed to crystallize.

[0071] Yield stress measurements were performed on chocolate samples as follows: the samples were melted at 45°C for 24 hours and then stirred in an IKA stirrer for 90 seconds at 300 rpm. Measurements were performed on an Anton Paar Rheometer (MCR51) following the IOCC2000 method. Yield stress values ​​were calculated using the Casson method. All measurements were performed in duplicate. A comparative experiment was carried out as described above, but instead of the fraction, commercially available acetone-deoiled lecithin was used (EmulPur® from Cargill).

[0072] The experiments demonstrated that the yield stress values ​​of the samples with the water-deoiled composition of the present invention were nearly identical to those achieved using commercially available lecithin.

Claims

1. 1. A method for extracting oil from an oil-containing phospholipid composition, comprising: (a) providing the oil-containing phospholipid composition, the composition comprising phospholipids and oil, the oil being in an amount of 20-80% by weight, based on the total weight of the oil-containing phospholipid composition; (b) mixing an extraction solvent consisting of water with the oil-containing phospholipid composition to obtain an aqueous composition, wherein the weight ratio of composition to water is between 6.0:1.0 and 1.3:1.0; (c) separating the aqueous composition into an oil-enriched fraction and an oil-depleted fraction using centrifugation, wherein the oil-depleted fraction comprises water and phospholipids; (d) removing the separated oil-enriched fraction to obtain an aqueous oil-depleted fraction comprising phospholipids; (e) freeze-drying the aqueous oil-depleted fraction to obtain a dry oil-depleted fraction comprising phospholipids.

2. 2. The method of claim 1, wherein the amount of oil contained by the oil-containing phospholipid composition is 40 to 78% by weight, more preferably 50 to 76% by weight, and most preferably 60 to 75% by weight.

3. 3. The method of claim 1 or 2, wherein the oil-containing phospholipid composition is obtained by degumming a raw oil.

4. The raw oil is a vegetable oil, and the vegetable oil is acai oil, acrocomia oil, almond oil, babassu oil, blackcurrant seed oil, borage seed oil, rapeseed oil, cashew oil, castoreum oil, coconut oil, coriander oil, corn oil, cottonseed oil, cranberry oil, linseed oil, grapeseed oil, hazelnut oil, other nut oils, hemp seed oil, potato coral oil, jojoba oil, macadamia nut oil, mango kernel oil, cardamom oil, mustard oil, or cow's foot oil.

4. The method of claim 3, wherein the oil is selected from the group of oils consisting of olive oil, palm oil, palm kernel oil, palm olein oil, peanut oil, pecan oil, pine kernel oil, pistachio oil, poppy oil, rice germ oil, safflower oil, camellia oil, sesame oil, shea butter oil, soybean oil, sunflower oil, tall oil, camellia oil, walnut oil, "natural" grade oils having fatty acid compositions modified through genetically modified organisms (GMO) or traditional breeding, and mixtures of the foregoing oils.

5. 5. The method according to any one of claims 1 to 4, wherein the oil-containing phospholipid composition contains phospholipids in an amount of at least 20% by weight, more preferably at least 40% by weight, and most preferably at least 60% by weight, based on the weight of the composition, as determined by Lange R., Fiebig HJ. (1999) : Separation of phospholipids, DGF Standard Method, Fett / Lipid 101: 77-79 or the acetone insolubles method according to AACC International Method 58-35.

01.

6. 6. The method of any one of claims 1 to 5, wherein the weight ratio of composition to water is from 5.0:1.0 to 1.5:1.0, more preferably from 4.0:1.0 to 2.0:1.0, and most preferably from 3.5:1.0 to 2.5:1.

0.

7. 7. The method of any one of claims 1 to 6, wherein the oil-containing phospholipid composition is heated to 90°C or less, more preferably 80°C or less, and most preferably 70°C or less, before mixing with the water in step b.

8. 8. The method according to any one of claims 1 to 7, wherein the temperature of the water mixed with the oil-containing phospholipid composition in step b is 95°C or less, more preferably 85°C or less, and most preferably 75°C or less.

9. 9. The method of any one of claims 1 to 8, wherein the separation step is carried out for a period of from 1 hour to 120 hours.

10. 10. The method according to any one of claims 1 to 9, wherein the separation of the aqueous composition into the oil-rich phase and the oil-depleted fraction is carried out using centrifugal force.

11. 11. The method according to any one of claims 1 to 10, wherein the oil-depleted fraction is dried to a moisture content of maximum 5.0 wt.%, more preferably maximum 2.0 wt.%, most preferably maximum 1.0 wt.%.

12. The method of any one of claims 1 to 11, wherein steps c) to d) are repeated at least once.

Images