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A kind of hyperbranched polysulfide polyamine hydrochloride and preparation method thereof

A technology of polyamine hydrochloride and amine hydrochloride, which is applied in the direction of chemicals used in biological control, antibacterial drugs, disinfectants, etc., can solve the cumbersome synthesis steps, reduce the number of effective functional groups, and limit the antibacterial effect of products Performance and other issues, to achieve the effect of fast diffusion speed and significant bactericidal effect

Active Publication Date: 2021-04-16
YANTAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the existing dendrimers are synthesized by an iterative method, and the synthesis steps are very cumbersome. For example, the synthetic products of each step of the reaction must be purified to prepare the polymer
Compared with dendritic polymers, the synthesis method of hyperbranched polymers is simple, but due to the randomness (that is, uncontrollability) of polymer chemical reactions, there are defects in the structure of hyperbranched polymers, and these defects embedding parts Quaternary ammonium salt functional groups, which reduce the number of effective functional groups that actually come into contact with the bacterial cell membrane, therefore, also limit the antibacterial properties of the product

Method used

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  • A kind of hyperbranched polysulfide polyamine hydrochloride and preparation method thereof
  • A kind of hyperbranched polysulfide polyamine hydrochloride and preparation method thereof
  • A kind of hyperbranched polysulfide polyamine hydrochloride and preparation method thereof

Examples

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Embodiment 1

[0047] A kind of synthetic method of hyperbranched polythioether polyamine hydrochloride, one of synthetic reaction route is as follows:

[0048]

[0049]

[0050] The above is the reaction route of Example 1 taking propargyl glycidyl ether and cysteamine hydrochloride as an example for the synthesis of hyperbranched polythioether polyamine hydrochloride as starting materials, wherein, a, b, c, d, e, f is a positive integer, which is the number of molecules of the compound participating in the reaction, and the products (1)-(4) correspond to the α-epoxy-ω-amine hydrochloride intermediates of 0-3 times of epoxy-amine reaction respectively.

[0051] The specific operation steps are as follows:

[0052] S1: Add 0.336g (3mmol) of propargyl glycidyl ether, 0.681g (6mmol) of cysteamine hydrochloride, and 0.035g (0.15mmol) of benzoin dimethyl ether into a 10ml single-necked round-bottomed flask containing small magnets and 6.1 g methanol. After nitrogen protection for 30min, ...

Embodiment 2

[0065] A kind of synthetic method of hyperbranched polythioether polyamine hydrochloride, comprises the following steps:

[0066] S1: Add 0.671g (6mmol) propargyl glycidyl ether, 1.021g (9mmol) cysteamine hydrochloride, 0.014g (0.06mmol) and 15.3g methanol to a 25ml single-necked round bottom flask containing a small magnet - Water (volume ratio 9:1). At a light intensity of 6000μW / cm 2 Irradiate and react under ultraviolet light for 12 hours to obtain a light yellow transparent solution

[0067]S2: Turn on the stirring device, and raise the temperature to 60°C, and then add 0.81g (4.5mmol) sodium methoxide solution at a uniform speed within 10 hours to the α-epoxy-ω-amine hydrochloride solution obtained in step S1 (mass fraction is 30%), then continue to react for 60 hours.

[0068] S3: After the reaction, centrifuge to remove solid sodium chloride, concentrate the supernatant with a rotary evaporator and precipitate in anhydrous ether three times, collect the precipitated...

Embodiment 3

[0072] A kind of synthetic method of hyperbranched polythioether polyamine hydrochloride, comprises the following steps:

[0073] S1: Dissolve 0.456g (4mmol) of allyl glycidyl ether, 0.409g (3.6mmol) of cysteamine hydrochloride, and 0.009 (0.04mmol) of photoinitiator α,α'-diethoxyacetophenone in 7.8g of methanol-ethanol (volume ratio 4:1) mixed solution, and then at a light intensity of 9000μW / cm 2 After 8 hours of reaction in an ice-water bath under the irradiation of ultraviolet light, a solution of α-epoxy-ω-amine hydrochloride was obtained.

[0074] S2: Turn on the stirring device, and raise the temperature to 60°C, and then add 0.335g (1.8mmol) of sodium methoxide at a uniform rate within 15 hours to the α-epoxy-ω-amine hydrochloride solution obtained in step S1 Methanol solution (mass fraction is 30%), reacted at 60°C for 48 hours.

[0075] S3: After the reaction, centrifuge to remove solid sodium chloride, concentrate the supernatant with a rotary evaporator and preci...

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Abstract

The invention discloses a hyperbranched polysulfide polyamine hydrochloride and a preparation method thereof. The present invention affects the primary amine groups in the reaction system by adjusting the addition method of the sodium methoxide solution, thereby changing the process of the entire chemical reaction, and the competition relationship between the primary amine group and the secondary amine group and the addition reaction of the epoxy group, thereby regulating The degree of branching and the number of useful functional groups of hyperbranched polysulfide fungicides. Use ultraviolet light to trigger allyl glycidyl ether and cysteamine hydrochloride solution in equimolar amounts to obtain the intermediate compound, then slowly add sodium methoxide solution, react at 60°C for 8-24 hours, and obtain hyperbranched polysulfide polyamine Hydrochloride fungicide. Among them, under stirring conditions, slowly dropwise add 1 / 2 molar sodium methoxide solution of the intermediate to obtain a product with a branching degree of 0.92 and a molecular weight distribution coefficient of 1.24. The periphery of the molecule contains 15.9 quaternary ammonium salt groups, and its aqueous solution has the highest bactericidal efficiency.

Description

technical field [0001] The invention relates to a hyperbranched polythioether polyamine hydrochloride and a preparation method thereof, belonging to the technical field of new polymer materials. Background technique [0002] Polymers are a class of organic materials that use various methods to link small molecular monomers through chemical bonds. Such materials generally have the characteristics of low density, excellent corrosion resistance, and good comprehensive performance, and have been widely used as plastics, rubber, fibers, etc. Like traditional metals and inorganic materials, the structure of polymer materials (such as molecular composition, molecular chain topology, condensed matter structure, etc.) directly affects its performance. Moreover, polymers have very good application prospects in many fields such as resin modifiers, drug delivery and release, and sensors. Hyperbranched polymers can be regarded as dendritic polymers with imperfect structures, and their ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G83/00A01P1/00A61P31/04
CPCA61P31/04C08G83/005
Inventor 郑耀臣刘健张谦班庆福高正国高璇
Owner YANTAI UNIV
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