Composition containing crystal choline and preparation method thereof
By introducing double bonds and carboxylate ions into the glycerol phospholipid choline molecule, the problem of glycerol phospholipid choline easily absorbing water and agglomeration in feed is solved, which improves dispersion and compatibility, improves animal health and feed stability, and promotes nutrient absorption.
Patent Information
- Application Number
- CN202510588406.4
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2025-05-08
- Publication Date
- 2025-08-15
- Estimated Expiration
- 2045-05-08
AI Technical Summary
In the prior art, glycerol phospholipid choline easily absorbs moisture in feed, causing particle agglomeration, affecting dispersion uniformity and absorption efficiency, and may cause gastrointestinal irritation and intestinal diseases, destroying feed stability and storage period.
Double bonds are introduced by reacting maleic anhydride with glycerol phospholipid choline and polymerizing with sodium acrylate to form a polymerized structure, introducing carboxylate ions, neutralizing ammonium charge, inhibiting particle agglomeration, improving dispersion and compatibility, and reducing the risk of gastrointestinal stimulation.
Effectively inhibit pellet agglomeration, ensure feed stability and composition uniformity, improve animal absorption efficiency, reduce intestinal diseases risks, optimize nutrient absorption, and improve animal growth performance.
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Abstract
Description
Technical Field
[0001] The present invention relates to the technical field of feed, and in particular to a composition containing crystalline choline and a preparation method thereof. Background Art
[0002] As an amphoteric surfactant with both a hydrophilic phosphorylcholine group and a hydrophobic fatty acid chain, glycerophospholipid choline plays an important role in multiple fields due to its excellent emulsification and biocompatibility. In cosmetics, it not only acts as a skin conditioner to improve dry and rough skin texture and maintain skin softness, smoothness, and elasticity, but also increases skin moisture content and reduces water loss through its moisturizing properties. In the field of pharmaceutical intermediates, as a key component of biomembranes, it participates in nerve impulse transmission and cell membrane synthesis and repair, and has significant effects on improving memory and cognitive function. It is widely used in the treatment of neurological diseases such as multiple sclerosis and Alzheimer's disease. In the feed industry, it acts as a nutritional supplement to promote animal lipid metabolism, optimize fat utilization, and reduce deposition, thereby improving growth performance and increasing feed conversion rate.
[0003] In the feed industry, existing technologies usually physically mix glycerophosphatidylcholine directly into feed raw materials in appropriate proportions according to different animal species, growth stages and feed types, or add it after making it into premixes or inclusion compounds with other nutrients to facilitate its dispersion in the feed and facilitate its effect after ingestion by animals.
[0004] However, the application of glycerophosphatidylcholine in the prior art has obvious defects. Because its molecular structure contains multiple active groups and contains hygroscopic ammonium groups, it is very easy to absorb moisture in the environment in the feed formula, especially under storage conditions with high humidity, and particles are prone to agglomeration. This agglomeration will not only affect the uniformity of the dispersion of glycerophosphatidylcholine in the feed, resulting in uneven intake of effective ingredients when the animal ingests it, but will also reduce its absorption efficiency in the animal body, weakening the function of promoting lipid metabolism, etc. On the other hand, the agglomeration after water absorption may also cause phase separation problems during the placement of the feed, that is, physical separation from other ingredients, destroying the stability of the feed formula, affecting product quality and storage period, and adversely affecting the production, transportation and long-term storage of the feed. In addition, the presence of active groups and the agglomeration and phase separation phenomena will not only change the physical properties of the feed, but also increase the risk of irritation of the feed to the gastrointestinal tract of the animal, leading to intestinal diseases such as diarrhea in the animal, thereby interfering with the normal absorption and digestion of nutrients, and ultimately having an adverse effect on the growth and development of the animal.
[0005] In summary, a new technical solution is urgently needed to solve the problems existing in the existing technology. Summary of the Invention
[0006] Based on this, the present invention provides a composition containing crystalline choline and a preparation method thereof. The present invention introduces a double bond into the molecular structure through a chemical reaction between maleic anhydride and glycerophosphatidylcholine, and then through polymerization with sodium acrylate, while forming a polymeric structure, further introduces carboxylate ions into the modified glycerophosphatidylcholine molecular chain. Through the above technical solution, particle agglomeration and system phase separation can be effectively suppressed, ensuring feed stability and ingredient uniformity. It can also improve the dispersibility of glycerophosphatidylcholine in feed, avoid reducing animal absorption efficiency, and reduce the risk of irritation to the animal's gastrointestinal mucosa, 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 with glycerophosphatidylcholine and then polymerizing 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, mixing maleic anhydride and glycerophosphatidylcholine, stirring and reacting to obtain glycerophosphatidylcholine containing double bonds;
[0016] S2, blending the double-bond-containing glycerophosphatidylcholine and sodium acrylate, adding an initiator, and heating for reaction to obtain modified glycerophosphatidylcholine;
[0017] S3. Mix all ingredients uniformly to obtain a composition containing crystalline choline.
[0018] Furthermore, in step S1, the molar ratio of maleic anhydride to glycerophosphatidylcholine is 1:(1-5).
[0019] Furthermore, in step S2, the mass ratio of the double-bond-containing glycerophospholipid choline to sodium acrylate is 1:(0.1-0.9).
[0020] Furthermore, in step S2, the heating temperature is 60-80°C.
[0021] Another object of the present invention is to provide an application of the composition containing crystalline choline.
[0022] The present invention has the following beneficial effects:
[0023] The present invention introduces a double bond in the molecular structure by the chemical reaction of maleic anhydride and glycerophospholipid choline, and then, by polymerization with sodium acrylate, while forming a polymeric structure, further introduces a carboxylate ion in the modified glycerophospholipid choline molecular chain. By this modification method, the carboxylate radical forms a dynamic equilibrium with the original ammonium group in the molecule by electrostatic attraction, effectively neutralizes the positive charge of the ammonium group, significantly suppresses particle agglomeration and system phase separation, improves the compatibility with other components, and solves the problem of poor feed stability and uneven effective ingredients caused by agglomeration. On the other hand, the branched structure formed by the polymerization reaction utilizes a steric effect to hinder the close packing between the modified glycerophospholipid choline molecules, further improves its dispersion uniformity in the feed formula, ensures the balance of the effective ingredient intake by animals, and avoids the problem of low absorption efficiency caused by uneven dispersion. In addition, the newly introduced group regulates the reactivity of the modified glycerophospholipid choline active group by electronic effect and steric hindrance, reducing the risk of excessive action of the modified glycerophospholipid choline active group on the gastrointestinal mucosa of the animal. The stable and uniform dispersion properties avoid irritation caused by excessive local concentrations, thereby reducing the likelihood of intestinal diseases such as diarrhea in animals, ensuring normal absorption and digestion of nutrients in the animal body, and providing strong support for their healthy growth. This series of mechanisms of action, through charge neutralization and three-dimensional conformation regulation, not only optimizes molecular properties and system stability, but also effectively reduces the risk of feed irritation to the animal's gastrointestinal tract. This overcomes the shortcomings of existing technologies using glycerophosphatidylcholine and provides a higher-quality technical solution for feed production. DETAILED DESCRIPTION
[0024] In order to more clearly illustrate the technical solutions of the present invention, the following examples are given. Unless otherwise stated, the raw materials, reactions and post-processing methods mentioned in the examples are common raw materials on the market and technical methods well known to those skilled in the art.
[0025] The terms "preferred," "preferably," "more preferred," and the like, used herein, refer to embodiments of the invention that may provide certain benefits under certain circumstances. However, other embodiments may also be preferred under the same or other circumstances. Furthermore, the recitation of one or more preferred embodiments does not imply that other embodiments are not useful, nor is it intended to exclude other embodiments from the scope of the invention.
[0026] It should be understood that, except in any operating examples, or where otherwise indicated, all numbers expressing, for example, quantities of ingredients used in the specification and claims are to be understood as being modified in all instances by the term "about." Accordingly, unless indicated to the contrary, the numerical parameters set forth in the following specification and appended claims are approximations that may vary depending upon the desired properties to be obtained by the present 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 salts: sodium chloride: calcium hydrogen phosphate: magnesium sulfate: potassium dihydrogen sulfate = 3:3:2:5, m / m / m / m.
[0030] The water in the present invention is all deionized water.
[0031] The "parts" in the present invention refer 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 with glycerophosphatidylcholine and then polymerizing with sodium acrylate.
[0037] The method for preparing the above-mentioned composition containing crystalline choline comprises the following steps:
[0038] S1. Using dichloromethane as a solvent, maleic anhydride and glycerophosphatidylcholine were mixed (maleic anhydride: glycerophosphatidylcholine = 1:2, n / n), and the mixture was stirred at room temperature for 5 h. After the reaction, the product was separated and purified with a dichloromethane-methanol mixed solvent (dichloromethane: methanol = 1:1, v / v), and then vacuum-dried. It was then purified with a tetrahydrofuran-water mixed solvent (tetrahydrofuran: water = 1:1, v / v) and vacuum-dried to obtain a glycerophosphatidylcholine containing a double bond;
[0039] S2. Using a methanol-water mixed solvent (methanol:water=1:1, v / v) as a solvent, the double-bond glycerophosphatidylcholine and sodium acrylate were blended (double-bond glycerophosphatidylcholine:sodium acrylate=1:0.5, m / m), sodium persulfate (1 wt% of the reactant) was added, and the mixture was heated at 80° C. for 12 h, filtered, and dried to obtain a modified glycerophosphatidylcholine;
[0040] S3. Mix all the ingredients uniformly according to the above mass fractions 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 with glycerophosphatidylcholine and then polymerizing 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 with glycerophosphatidylcholine and then polymerizing 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 not performed. In step S3, the modified glycerophospholipid choline is replaced by glycerophospholipid choline containing double bonds. The amounts of other ingredients and the preparation method are the same as those in Example 1.
[0054] Comparative Example 2
[0055] A composition containing crystalline choline. The difference between this comparative example and Example 1 is that step S1-2 is not performed. In step S3, the mass of the modified glycerophosphatidylcholine is replaced by a physical mixture of glycerophosphatidylcholine and sodium acrylate (glycerophosphatidylcholine: sodium acrylate = 1:0.5, m / m). The amounts of other ingredients and the preparation method are the same as those in Example 1.
[0056] Test Case
[0057] Performance tests were performed on the crystalline choline-containing compositions of Examples 1-3 and Comparative Examples 1-2.
[0058] Test method:
[0059] (1) The properties of the composition containing crystalline choline were observed on day 0 and after storage at room temperature for 6 months.
[0060] (2) Clean and chop alfalfa to a length of 2-3 cm, then compost it for fermentation for 4 days. The moisture content is adjusted to 5%. The treated alfalfa is mixed with a composition containing choline crystals in a ratio of 1:6 by weight to form a pig feed.
[0061] 180 30-day-old piglets of similar weight were randomly divided into nine groups of 20 each. Each group was housed in single-pen pens of identical size and environment. They were fed and managed according to standard farm procedures using the aforementioned feed, with free access to food and water. The trial lasted for 90 days. Testing items: ① The piglets in each pen were weighed on an empty stomach at 9:00 a.m. on the start and end days of the trial, and their average daily weight gain was calculated. ② The piglets' defecation was observed daily after the start of the trial, and the number of piglets with diarrhea and their duration were recorded. The diarrhea rate was calculated by dividing the number of piglets with diarrhea in each replicate by the total number of piglets housed.
[0062] The test results are shown in Table 1.
[0063] Table 1 Performance test results
[0064]
[0065]
[0066] The test results show that the composition containing choline crystals of the present invention has a uniform color, is dry, has no agglomeration, and has stable properties after being stored for 6 months. Pigs fed with the composition containing choline crystals of the present invention have better digestion and do not experience abdominal distension, diarrhea, etc. The composition has a better nutritional effect and can effectively promote rapid growth of pigs, with a higher 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 embodied 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 illustrative and non-restrictive, and the scope of the invention is defined by the appended claims rather than the foregoing description, and it is intended that all variations that come within the meaning and range of equivalents of the claims be embraced therein.
[0068] In addition, it should be understood that although this specification is described in terms of implementation methods, not every implementation method contains only one independent technical solution. This narrative method of the specification is only for the sake of clarity. Those skilled in the art should regard the specification as a whole. The technical solutions in each embodiment can also be appropriately combined to form other implementation methods that can be understood by those skilled in the art.
Claims
1. A composition containing crystalline choline, characterized in that The composition includes the following components in parts by weight: The modified glycerophosphatidylcholine is a product obtained by reacting maleic anhydride with glycerophosphatidylcholine and then polymerizing with sodium acrylate.
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 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).
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 consists 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. The method for preparing the composition containing crystalline choline according to any one of claims 1 to 5, characterized in that: The steps include: S1, mixing maleic anhydride and glycerophosphatidylcholine, stirring and reacting to obtain glycerophosphatidylcholine containing double bonds; S2, blending the double-bond-containing glycerophosphatidylcholine and sodium acrylate, adding an initiator, and heating for reaction to obtain modified glycerophosphatidylcholine; S3. Mix all ingredients uniformly to obtain a composition containing crystalline choline.
7. The method for preparing the composition containing crystalline choline according to claim 6, characterized in that: In step S1, the molar ratio of maleic anhydride to glycerophosphatidylcholine is 1:(1-5).
8. The method for preparing the composition containing crystalline choline according to claim 6, characterized in that: In step S2, the mass ratio of the double-bond-containing glycerophospholipid choline to sodium acrylate is 1:(0.1-0.9).
9. The method for preparing the composition containing crystalline choline according to claim 6, characterized in that: In step S2, the heating temperature is 60-80°C.
10. Use of the composition containing crystalline choline according to any one of claims 1 to 5.
Citation Information
Patent Citations
Composition containing choline chloride and preparation method thereof
CN118000305A
Choline fodder additive - contg choline salt and malt germ - and / or hydrolysed starch[DE]Cholinpraeparat
DE2022072A1