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Preparation method of cationization hyaluronic acid

A hyaluronic acid and cationization technology, which is applied in the field of preparation of cationized hyaluronic acid, can solve the problems of energy waste, many post-processing steps, and difficulty in repeating, and achieve low cost of use, simple operation, and moderate degree of cationization Effect

Inactive Publication Date: 2018-02-27
YANGZHOU ZHONGFU BIOTECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The first method is to react at room temperature in an aqueous medium, but we have experimented many times and it is difficult to repeat their results by this method
The second method is in 65% ethanol aqueous solution, at 60 O Reaction at about C for 1 hour, but its disadvantage is that there are many post-processing steps, even if the solvent can be recovered, energy will be wasted

Method used

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  • Preparation method of cationization hyaluronic acid
  • Preparation method of cationization hyaluronic acid
  • Preparation method of cationization hyaluronic acid

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preparation example Construction

[0020] The invention provides a preparation method of cationized hyaluronic acid, in aqueous medium, under the action of alkali and phase transfer catalyst, 25~40 o Under the condition of C, let hyaluronic acid (sodium) react with the cationization reagent-glycidyltrimethylammonium chloride, after the reaction, add ethanol to precipitate the cationized hyaluronic acid.

[0021] The reaction formula described above is as follows:

[0022]

[0023] Part of R in the above formula is hydrogen, and part of it is a group containing a quaternary ammonium salt.

[0024] In the embodiment of the present invention, the cationizing agent is glycidyltrimethylammonium chloride, and the mass ratio of the agent to hyaluronic acid (sodium) is 1:1.

[0025] In the embodiments of the present invention, the alkali is NaOH, and the mass ratio of NaOH to hyaluronic acid (sodium) is 0.5-1:20.

[0026] In the embodiment of the present invention, the phase transfer catalyst is cetyltrimethylammo...

Embodiment 1

[0036] Synthesis reaction: 20 grams of hyaluronic acid (the molecular weight of Zhongfu hyaluronic acid is 1.40-1.6 million Da, the same below), 20 grams of cationic reagent, 2 grams of phase transfer catalyst (tsab), 40 ml of water, 3 M sodium hydroxide 6 ml of the solution was added to a 1-liter three-necked round-bottomed flask, and the temperature was lower than 30 o C conditions for 3 hours. Slowly add 350 ml of absolute ethanol to the flask under stirring to precipitate cationized hyaluronic acid. Suction filtration (or decantation) to remove the liquid phase. Wash the filter cake (or the solid phase part) with 75% (volume ratio) alcohol for 3 times. 300 ml of 75% alcohol for the first time, stirred for half an hour, 200 ml of 75% alcohol for the second and third times, stirred for 20 minutes, and suction filtration or decantation was used for solid-liquid separation. The solid was dried with more than 99% (or acetone) isopropanol for more than 12 hours, filtered, and...

Embodiment 2

[0043] ② Group pilot stage, add 200 grams of hyaluronic acid, 200 grams of cationization reagent, 2 grams of phase transfer catalyst (tsab), 400 milliliters of water, and 60 milliliters of 3 M sodium hydroxide solution into a 5-liter three-necked round-bottomed flask in, at 25 oC conditions for 3 hours. Slowly add 3500 milliliters of absolute ethanol to the flask under stirring to precipitate the cationized hyaluronic acid. Suction filtration (or decantation) to remove the liquid phase. Wash the filter cake (or the solid phase part) with 75% (volume ratio) alcohol for 3 times. 3000 ml of 75% alcohol for the first time, stirred for half an hour, 2000 ml of 75% alcohol for the second and third times, stirred for 20 minutes, and suction filtration or decantation was used for solid-liquid separation. The solid was dried with more than 99% (or acetone) isopropanol for more than 12 hours, filtered, and then dried by freeze-drying to obtain 255.3 grams of cationized sodium hyaluro...

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Abstract

The invention relates to the field of macromolecule hydratant preparation, and particularly relates to a preparation method of novel cationization hyaluronic acid easily compatible to body compositions. According to the method, in water, under the action of alkali and a phase transfer catalyst, hyaluronic acid (sodium) and cationic reagent-glycidol trimethyl ammonium chloride are coupled to obtainthe cationization hyaluronic acid (sodium). The preparation method of the novel cationization hyaluronic acid provided by the invention adopts the water as a reaction medium so as to be reacted at room temperature or at the temperature slightly higher than the room temperature, is easy to control, high in cationization degree, completely in conformity with ideas of energy conservation, high efficiency, green and environmental protection, and suitable for industrialization.

Description

technical field [0001] The invention relates to the field of compound preparation, in particular to a preparation method of cationized hyaluronic acid. Background technique [0002] Hyaluronic acid (structural formula I), also known as uronic acid and hyaluronic acid, is a disaccharide unit polysaccharide composed of D-glucuronic acid and N-acetylglucosamine. The basic structure is composed of two disaccharide units D-glucose Large polysaccharides composed of uronic acid and N-acetylglucosamine. Unlike other mucopolysaccharides, it does not contain sulfur. Its hyaluronic molecule can carry more than 500 times of water, which is recognized as the best moisturizing ingredient today, and is widely used in skin care products and cosmetics. [0003] [0004] (I) [0005] Hyaluronic acid is negatively charged because it contains carboxyl functional groups. The surface of human skin and hair is also negatively charged. Good moisturizing effect. [0006] In order to make hya...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/08
CPCC08B37/0072
Inventor 魏涛朱翔张克伦孙斌
Owner YANGZHOU ZHONGFU BIOTECH CO LTD