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Method for synthesizing polyhexamethylene biguanide from monoguanidine intermediate

A technology for polyhexamethylene biguanide and an intermediate is applied in the field of polybiguanide compound synthesis, can solve the problems of difficult control of the reaction process, difficult polycondensation reaction, low content of biguanide groups, etc., and achieves short production cycle and simple preparation process. Effect

Active Publication Date: 2021-12-10
DALIAN BIO CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] However, the problem with the one-step method is that the sodium chloride produced by the reaction cannot be removed, and the reaction process is difficult to control.
The main problem that this route exists is that polycondensation reaction is difficult to carry out completely, and the product biguanide group content that obtains is lower, and the ammonium chloride that produces is difficult to remove

Method used

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  • Method for synthesizing polyhexamethylene biguanide from monoguanidine intermediate
  • Method for synthesizing polyhexamethylene biguanide from monoguanidine intermediate
  • Method for synthesizing polyhexamethylene biguanide from monoguanidine intermediate

Examples

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Effect test

Embodiment 1

[0042] A method for synthesizing polyhexamethylene biguanide by a monoguanidine intermediate, the steps are as follows:

[0043] (1) Monomer synthesis: Add hexamethylenediamine hydrochloride (18.9g, 0.1mol), methanol 150g, sodium dicyandiamide (8.9g, 0.1mol) into the reaction kettle, heat up to reflux, stir for 2h, filter , to obtain the filtrate containing monoguanidine intermediate 1-(6-aminohexyl)-3-cyanoguanidine, the filter cake is rinsed 2 times with methanol, each with methanol 20g, and the rinse solution is combined with the filtrate;

[0044] (2) Polymerization reaction: Heating the combined filtrate in step (1), steaming out methanol (recovery), remaining viscous jelly (~22g) in the kettle, adding appropriate amount of water to aid dissolution, continuing to heat up to 140°C, stirring Polymerization reaction 4h, obtain polyhexamethylene biguanide crude product;

[0045] (3) Purification: Add 80 g of deionized water to the crude product of polyhexamethylene biguanide...

Embodiment 2

[0048] A method for synthesizing polyhexamethylene biguanide by a monoguanidine intermediate, the steps are as follows:

[0049] (1) Synthesis of monomers: add hexamethylenediamine (11.6g, 0.1mol) and 150g of n-butanol in the reaction kettle, dropwise add 22.8g of 32% hydrochloric acid, stir and heat up, and azeotropically distill off water until the temperature of the kettle is 112°C. Add sodium dicyandiamide (8.9g, 0.1mol) to the kettle again, heat up to reflux, stir and react for 2h, filter to obtain the filtrate containing monoguanidine intermediate 1-(6-aminohexyl)-3-cyanoguanidine , the filter cake is rinsed twice with n-butanol, each with 20 g of n-butanol, and the rinse solution is combined with the filtrate;

[0050] (2) Polymerization reaction: Heating the combined filtrate in step (1), after steaming out n-butanol, the remaining viscous jelly (~22g, target ion C 8 h 18 N 5 + , The theoretical molecular weight is 184.16, the test value is 183.98, and the positive...

Embodiment 3

[0054] A method for synthesizing polyhexamethylene biguanide by a monoguanidine intermediate, the steps are as follows:

[0055](1) Monomer synthesis: add hexamethylenediamine (11.6g, 0.1mol) and 150g ethanol to the reaction kettle, add dropwise 23.1g of 85% phosphoric acid, stir and heat up to reflux (~80°C), then add bis Sodium cyanamide (8.9g, 0.1mol), warming up to reflux, stirred for 4h, filtered to obtain the filtrate containing the monoguanidine intermediate 1-(6-aminohexyl)-3-cyanoguanidine, the filter cake was rinsed with ethanol Wash twice, each time with 20 g of ethanol, and combine the eluent and the filtrate;

[0056] (2) Polymerization reaction: Heating the combined filtrate in step (1), steaming out the ethanol, leaving a viscous jelly (~25g) in the kettle, adding an appropriate amount of water to help dissolve, continue to heat up to 155°C, and stir for 3h , to obtain the crude product of polyhexamethylene biguanide;

[0057] (3) Purification: Add 80 g of dei...

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Abstract

The invention provides a method for synthesizing polyhexamethylene biguanide from a monoguanidine intermediate, and relates to the technical field of synthesis of polyhexamethylene biguanide compounds. The method comprises the following steps: firstly, taking dicyandiamide salt and hexanediamine or hexanediamine salt as raw materials, carrying out unilateral reaction to generate a monoguanidine intermediate, carrying out simple treatment, and conducting heating and auto-polymerization to obtain PHMB. The method not only can avoid the complicated treatment process in the traditional synthesis of the biguanide intermediate, but also can avoid the defects that the salt content of the product produced by a one-pot method is too high and is difficult to remove, the synthesis and post-treatment processes are simple, the product quality is easy to control, and the method is a simple, convenient and efficient synthesis method.

Description

technical field [0001] The invention relates to the technical field of synthesis of polybiguanide compounds, in particular to a method for synthesizing polyhexamethylene biguanide from a monoguanidine intermediate. Background technique [0002] Polyhexamethylene biguanide (PHMB) is a high-efficiency, multi-purpose cationic polymer (the anion is generally chloride ion, and it can also be other anions), which has a strong ability to kill bacteria and viruses, and has a broad spectrum of bacteria and The antibacterial effect lasts for a long time, and the bactericidal effect is less affected by factors such as ambient temperature, pH and organic matter. It is widely used in the fields of medicine, leather processing, industrial and civilian water, etc. It is often used in sanitary wipes, household disinfectants, aquaculture, wound disinfection, gynecological lotion, hand disinfectants, disinfectants in beverage and food processing industries, and sewage treatment. Flocculation...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G73/00
CPCC08G73/00
Inventor 强新新王金凤张晓娜安金星江雨瞳杨兆辉赵建新顾振鹏
Owner DALIAN BIO CHEM
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