A composition containing crystalline choline and a method for its preparation

Abstract

The application provides a composition containing crystalline choline, which comprises the following components in mass fractions: 20-25 parts of soybean meal, 10-14 parts of peanut meal, 6-10 parts of corn flour, 1-2 parts of vitamins, 6-10 parts of rice bran, 3-5 parts of inorganic salt and 1-3 parts of modified glycerophospholipid choline; wherein the modified glycerophospholipid choline is a product after maleic anhydride and glycerophospholipid choline react, and a product after the product and sodium acrylate polymerize. The modified glycerophospholipid choline is added, the carboxylate and ammonium group charge are neutralized, the polymerization branched chain stereo conformation is regulated, the particle agglomeration and system phase separation can be effectively inhibited, the feed stability and ingredient uniformity can be ensured, the dispersibility of glycerophospholipid choline in the feed can be improved, the animal absorption efficiency is prevented from being reduced, the stimulation risk of the gastrointestinal mucosa of the animal is reduced, the intestinal diseases are reduced, the nutrient substance absorption and digestion are ensured, and an efficient solution is provided for the feed production.

Description

Technical Field

[0001] This invention relates to the field of feed technology, specifically to a composition containing crystalline choline and its preparation method. Background Technology

[0002] Glycerylphospholipid choline, an amphoteric surfactant possessing both hydrophilic phosphocholine groups and hydrophobic fatty acid chains, plays a vital role in multiple fields due to its excellent emulsifying and biocompatibility. In cosmetics, it not only acts as a skin conditioner to improve dry and rough skin, maintaining its softness, smoothness, and elasticity, but also increases skin moisture content and reduces water loss through its moisturizing properties. In the pharmaceutical intermediate field, as a key component of biological membranes, it participates in nerve impulse transmission and cell membrane synthesis and repair, showing significant effects on improving memory and cognitive function, and is widely used in the treatment of neurological diseases such as multiple sclerosis and Alzheimer's disease. In the feed industry, as a nutritional fortifier, it promotes lipid metabolism in animals, optimizes fat utilization, and reduces deposition, thereby improving growth performance and increasing feed conversion rate.

[0003] In the feed industry, existing technologies typically involve directly and physically mixing glycerophospholipids and choline into feed ingredients in appropriate proportions, depending on the animal species, growth stage, and feed type. Alternatively, they can be added after being formulated into premixes or packaged feeds with other nutrients, in order to facilitate dispersion in the feed and allow the animal to exert its effects after ingestion.

[0004] However, the application of glycerophosphatidylcholine in existing technologies has significant drawbacks. Due to the presence of multiple active groups in its molecular structure, including hygroscopic ammonium groups, it readily absorbs moisture from the environment in feed formulations, especially under high humidity storage conditions, leading to particle aggregation. This aggregation not only affects the uniformity of glycerophosphatidylcholine dispersion in feed, resulting in uneven intake of the effective components by animals, but also reduces its absorption efficiency in the animal body, weakening its functions such as promoting lipid metabolism. Furthermore, aggregation after water absorption may cause phase separation during feed storage, i.e., physical separation from other components, compromising the stability of the feed formulation, affecting product quality and shelf life, and adversely impacting feed production, transportation, and long-term storage. In addition, the presence of active groups, as well as aggregation and phase separation, not only alters the physical properties of the feed but may also increase the risk of gastrointestinal irritation in animals, leading to intestinal diseases such as diarrhea, thereby interfering with the normal absorption and digestion of nutrients, ultimately adversely affecting animal growth and development.

[0005] In conclusion, a new technical solution is urgently needed to address the problems existing in the current technology. Summary of the Invention

[0006] Based on this, the present invention provides a composition containing crystalline choline and a method for preparing the same. The present invention introduces double bonds into the molecular structure through a chemical reaction between maleic anhydride and glycerophosphatidylcholine. Subsequently, through polymerization with sodium acrylate, carboxylate ions are further introduced into the modified glycerophosphatidylcholine molecular chain while forming a polymeric structure. This technical solution effectively inhibits particle aggregation and phase separation, ensuring feed stability and component uniformity. It also improves the dispersibility of glycerophosphatidylcholine in feed, preventing reduced absorption efficiency in animals and reducing the risk of irritation to the gastrointestinal mucosa, thus providing an efficient solution for feed production.

[0007] One object of the present invention is to provide a composition containing crystalline choline, comprising the following components in parts by weight:

[0008]

[0009] The modified glycerophosphatidylcholine is a product obtained by reacting maleic anhydride and glycerophosphatidylcholine, and then polymerizing it with sodium acrylate.

[0010] Furthermore, the vitamin is selected from one or more of vitamin A, vitamin B, vitamin C, vitamin D, vitamin E, or vitamin K.

[0011] Furthermore, the vitamins are composed of vitamin A, vitamin C, vitamin D, vitamin E and vitamin K in a mass ratio of (1-5):(1-5):(2-8):(5-10):(2-8).

[0012] Furthermore, the inorganic salt is selected from one or more of sodium chloride, calcium hydrogen phosphate, magnesium sulfate, or potassium dihydrogen sulfate.

[0013] Furthermore, the inorganic salt is composed of sodium chloride, calcium hydrogen phosphate, magnesium sulfate, and potassium dihydrogen sulfate in a mass ratio of (1-5):(1-5):(1-5):(4-8).

[0014] Another object of the present invention is to provide a method for preparing the above-mentioned composition containing crystalline choline, comprising the following steps:

[0015] S1. Maleic anhydride and glycerophosphatidylcholine are mixed and stirred to react, yielding glycerophosphatidylcholine containing double bonds.

[0016] S2. The double-bonded glycerophosphatidylcholine and sodium acrylate are mixed together, an initiator is added, and the mixture is heated to react, thereby obtaining modified glycerophosphatidylcholine.

[0017] S3. Mix all the ingredients thoroughly to obtain a composition containing crystalline choline.

[0018] Further, in step S1, the molar ratio of maleic anhydride and glycerophospholipid choline is 1:(1-5).

[0019] Further, in step S2, the mass ratio of the double-bonded glycerophosphatidylcholine to sodium acrylate is 1:(0.1-0.9).

[0020] Furthermore, in step S2, the heating temperature is 60-80℃.

[0021] Another object of the present invention is to provide the application of the above-described composition containing crystalline choline.

[0022] The present invention has the following beneficial effects:

[0023] This invention introduces double bonds into the molecular structure through the chemical reaction of maleic anhydride and glycerophosphatidylcholine. Subsequently, through polymerization with sodium acrylate, carboxylate ions are further introduced into the modified glycerophosphatidylcholine molecular chain while forming a polymeric structure. Through this modification, the carboxylate ions and the existing ammonium groups in the molecule form a dynamic equilibrium through electrostatic attraction, effectively neutralizing the positive charge of the ammonium groups, significantly inhibiting particle aggregation and phase separation, and improving compatibility with other components. This solves the problems of poor feed stability and uneven distribution of active ingredients caused by aggregation. On the other hand, the branched structure formed by the polymerization reaction utilizes steric hindrance to prevent the close packing of modified glycerophosphatidylcholine molecules, further improving its dispersion uniformity in feed formulations, ensuring a balanced intake of active ingredients by animals, and avoiding low absorption efficiency due to uneven dispersion. Furthermore, the newly introduced groups, through electronic effects and steric hindrance, regulate the reactivity of the active groups of modified glycerophosphatidylcholine, reducing the risk of excessive interaction with the animal's gastrointestinal mucosa. The stable and uniform dispersion characteristics avoid irritation caused by excessively high local concentrations, thereby reducing the likelihood of intestinal diseases such as diarrhea in animals. This ensures the normal absorption and digestion of nutrients in the animal's body, providing strong support for healthy animal growth. This series of mechanisms of action, through charge neutralization and stereoconformity regulation, not only optimizes molecular properties and system stability but also effectively reduces the risk of feed irritation to the animal's gastrointestinal tract. It overcomes the shortcomings of existing technologies in the application of glycerophospholipids and choline, providing a superior technical solution for feed production. Detailed Implementation

[0024] To more clearly illustrate the technical solution of the present invention, the following embodiments are provided. Unless otherwise stated, the raw materials, reactions, and post-processing methods appearing in the embodiments are all commercially available raw materials and technical methods well known to those skilled in the art.

[0025] The terms "preferred," "more preferably," and "more suitable" used in this invention refer to embodiments of the invention that provide certain beneficial effects under certain circumstances. However, other embodiments may also be preferred under the same or other circumstances. Furthermore, the description of one or more preferred embodiments does not imply that other embodiments are unavailable, nor is it intended to exclude other embodiments from the scope of this invention.

[0026] It should be understood that, except in any operational instance or otherwise indicated, the amounts or all figures representing ingredients used, for example, in the specification and claims, should be understood to be modified by the term "about" in all cases. Therefore, unless otherwise stated, the numerical parameters set forth in the following specification and appended claims are approximate values ​​varying according to the desired performance to be obtained according to the invention.

[0027] The present invention uses the following raw materials:

[0028] Vitamins: Vitamin A: Vitamin C: Vitamin D: Vitamin E: Vitamin K = 3:2:3:6:5, m / m / m / m / m.

[0029] Inorganic salt: Sodium chloride: Calcium hydrogen phosphate: Magnesium sulfate: Potassium dihydrogen sulfate = 3:3:2:5, m / m / m / m.

[0030] All water used in this invention is deionized water.

[0031] In this invention, "parts" refers to parts by mass.

[0032] Example 1

[0033] A composition containing crystalline choline, comprising the following components in parts by weight:

[0034]

[0035]

[0036] The modified glycerophosphatidylcholine is a product obtained by reacting maleic anhydride and glycerophosphatidylcholine, and then polymerizing it with sodium acrylate.

[0037] The method for preparing the above-mentioned composition containing crystalline choline includes the following steps:

[0038] S1. Using dichloromethane as a solvent, maleic anhydride and glycerophosphatidylcholine were mixed (maleic anhydride:glycerophosphatidylcholine = 1:2, n / n) and stirred at room temperature for 5 hours. After the reaction was complete, the product was separated and purified using a dichloromethane-methanol mixed solvent (dichloromethane:methanol = 1:1, v / v), then dried under vacuum, and then purified again using a tetrahydrofuran-water mixed solvent (tetrahydrofuran:water = 1:1, v / v), and dried under vacuum to obtain glycerophosphatidylcholine containing double bonds.

[0039] S2. Using a methanol-water mixed solvent (methanol:water = 1:1, v / v) as the solvent, the double-bonded glycerophosphatidylcholine and sodium acrylate were blended (double-bonded glycerophosphatidylcholine:sodium acrylate = 1:0.5, m / m), and sodium persulfate (1 wt% of reactants) was added. The mixture was heated at 80°C for 12 h, filtered, and dried to obtain modified glycerophosphatidylcholine.

[0040] S3. Mix all the ingredients evenly according to the above-mentioned mass proportions to obtain a composition containing crystalline choline.

[0041] Example 2

[0042] A composition containing crystalline choline, comprising the following components in parts by weight:

[0043]

[0044] The modified glycerophosphatidylcholine is a product obtained by reacting maleic anhydride and glycerophosphatidylcholine, and then polymerizing it with sodium acrylate.

[0045] The preparation method of the above-mentioned composition containing crystalline choline is the same as that in Example 1.

[0046] Example 3

[0047] A composition containing crystalline choline, comprising the following components in parts by weight:

[0048]

[0049]

[0050] The modified glycerophosphatidylcholine is a product obtained by reacting maleic anhydride and glycerophosphatidylcholine, and then polymerizing it with sodium acrylate.

[0051] The preparation method of the above-mentioned composition containing crystalline choline is the same as that in Example 1.

[0052] Comparative Example 1

[0053] A composition containing crystalline choline. The difference between this comparative example and Example 1 is that step S2 is omitted. In step S3, the modified glycerophosphatidylcholine is replaced by glycerophosphatidylcholine containing double bonds. The amounts of other components and the preparation method are the same as in Example 1.

[0054] Comparative Example 2

[0055] A composition containing crystalline choline, the difference between this comparative example and Example 1 is that steps S1-2 are omitted, and in step S3, the modified glycerophosphatidylcholine is replaced by a physical mixture of glycerophosphatidylcholine and sodium acrylate (glycerophosphatidylcholine:sodium acrylate = 1:0.5, m / m), while the dosage of other components and the preparation method are the same as in Example 1.

[0056] Test case

[0057] The compositions containing crystalline choline in Examples 1-3 and Comparative Examples 1-2 were subjected to performance tests.

[0058] Test method:

[0059] (1) Observe the properties of the composition containing crystalline choline after 0 days and after 6 months of storage at room temperature.

[0060] (2) Take alfalfa, clean it, then crush it to a length of 2-3 cm, then pile it up for fermentation for 4 days, and adjust its moisture content to 5%. Mix the alfalfa treated above with a composition containing crystalline choline at a weight ratio of 1:6 and use it as pig feed.

[0061] One hundred and eighty 30-day-old piglets of similar weight were randomly divided into nine groups of 20 each. Each group was housed in a single-pen with identical dimensions and environment. They were fed and managed according to standard pig farm procedures using the aforementioned feed, with free access to feed and water. The experiment lasted 90 days. Test items: ① On the start and end days of the experiment, piglets in each pen were weighed at 09:00 AM on an empty stomach to calculate the average daily weight gain; ② After the start of the experiment, the defecation of piglets was observed daily, and the number of individuals experiencing diarrhea and the duration of diarrhea were recorded. The diarrhea rate was calculated by dividing the number of piglets with diarrhea per replicate by the total number of piglets.

[0062] The test results are shown in Table 1.

[0063] Table 1 Performance Test Results

[0064]

[0065]

[0066] The test results above show that the composition containing crystalline choline of the present invention, after being stored for 6 months, is uniform in color, dry, and free from agglomeration, and has stable properties. Pigs fed with the composition containing crystalline choline of the present invention have better digestion and do not experience bloating or diarrhea. The nutritional effect is better, which can effectively promote the rapid growth of pigs and increase the average daily weight gain.

[0067] It will be apparent to those skilled in the art that the present invention is not limited to the details of the exemplary embodiments described above, and that the invention can be implemented in other specific forms without departing from the spirit or essential characteristics of the invention. Therefore, the embodiments should be considered in all respects as exemplary and non-limiting, and the scope of the invention is defined by the appended claims rather than the foregoing description. Thus, it is intended that all variations falling within the meaning and scope of equivalents of the claims be included within the present invention.

[0068] Furthermore, it should be understood that although this specification describes embodiments, not every embodiment contains only one independent technical solution. This narrative style is merely for clarity. Those skilled in the art should consider the specification as a whole, and the technical solutions in each embodiment can also be appropriately combined to form other embodiments that can be understood by those skilled in the art.

Claims

1. A composition containing crystalline choline, characterized in that, The ingredients include the following parts by weight: 20-25 parts soybean meal 10-14 parts peanut meal 6-10 parts cornmeal 1-2 servings of vitamins 6-10 parts rice bran 3-5 parts of inorganic salts Modified glycerophosphatidylcholine 1-3 parts; The preparation method of modified glycerophosphatidylcholine includes the following steps: S1. Using dichloromethane as a solvent, maleic anhydride and glycerophospholipid choline were mixed at a molar ratio of 1:2 and stirred at room temperature for 5 h. After the reaction was complete, the product was separated and purified with a dichloromethane-methanol mixed solvent at a volume ratio of 1:1, then dried under vacuum, and then purified with a tetrahydrofuran-water mixed solvent at a volume ratio of 1:1 and dried under vacuum to obtain glycerophospholipid choline containing double bonds. S2. Using a methanol-water mixture with a volume ratio of 1:1 as the solvent, the glycerophosphatidylcholine containing double bonds and sodium acrylate are mixed at a mass ratio of 1:0.

5. 1 wt% of sodium persulfate is added to the reactants, and the mixture is heated at 80°C for 12 h. After filtration and drying, modified glycerophosphatidylcholine is obtained.

2. The composition containing crystalline choline according to claim 1, characterized in that, The vitamin is selected from one or more of vitamin A, vitamin B, vitamin C, vitamin D, vitamin E, or vitamin K.

3. The composition containing crystalline choline according to claim 2, characterized in that, The vitamins consist of vitamins A, C, D, E, and K in a mass ratio of (1-5):(1-5):(2-8):(5-10):(2-8).

4. The composition containing crystalline choline according to claim 1, characterized in that, The inorganic salt is selected from one or more of sodium chloride, calcium hydrogen phosphate, magnesium sulfate, or potassium dihydrogen sulfate.

5. The composition containing crystalline choline according to claim 4, characterized in that, The inorganic salt is composed of sodium chloride, calcium hydrogen phosphate, magnesium sulfate and potassium dihydrogen sulfate in a mass ratio of (1-5):(1-5):(1-5):(4-8).

6. A method for preparing the composition containing crystalline choline according to any one of claims 1-5, characterized in that, Includes the following steps: S1. Using dichloromethane as a solvent, maleic anhydride and glycerophospholipid choline were mixed at a molar ratio of 1:2 and stirred at room temperature for 5 h. After the reaction was complete, the product was separated and purified with a dichloromethane-methanol mixed solvent at a volume ratio of 1:1, then dried under vacuum, and then purified with a tetrahydrofuran-water mixed solvent at a volume ratio of 1:1 and dried under vacuum to obtain glycerophospholipid choline containing double bonds. S2. Using a methanol-water mixture with a volume ratio of 1:1 as the solvent, the glycerophosphatidylcholine containing double bonds and sodium acrylate are mixed at a mass ratio of 1:0.

5. 1 wt% of sodium persulfate is added to the reactants, and the mixture is heated at 80°C for 12 h. After filtration and drying, modified glycerophosphatidylcholine is obtained. S3. Mix all the ingredients thoroughly to obtain a composition containing crystalline choline.

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