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PVP compound with terminal containing dithioester, topological polymer, and preparation methods for PVP compound with terminal containing dithioester and topological polymer

A technology of dithioesters and compounds, which is applied in the field of synthesis of antifouling compounds, can solve problems such as difficulty in realization, difficulty in large-area use, and difficulty in scale-up, and achieve the effects of excellent adhesion and excellent biocompatibility

Active Publication Date: 2020-05-12
JIANGHAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these preparation methods require special functional groups on the surface of the substrate for grafting polymer chains, and at the same time, a certain grafting density is required to achieve good anti-protein and marine biological adhesion effects, so this method is difficult to realize industrially Large, difficult to scale and use in large areas

Method used

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  • PVP compound with terminal containing dithioester, topological polymer, and preparation methods for PVP compound with terminal containing dithioester and topological polymer
  • PVP compound with terminal containing dithioester, topological polymer, and preparation methods for PVP compound with terminal containing dithioester and topological polymer
  • PVP compound with terminal containing dithioester, topological polymer, and preparation methods for PVP compound with terminal containing dithioester and topological polymer

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preparation example Construction

[0035] For the second solution of the present invention, the present invention provides a kind of preparation method of the PVP compound containing dithioester at the end, comprising the following steps:

[0036] Compound I is reacted with α-bromoisobutyryl bromide from a compound containing a hydroxyl group at the end, compound I is reacted with potassium ethyl xanthate to obtain compound II, and compound II reacts with N-ethylene under the action of the first initiator Pyrrolidone reaction to obtain a PVP compound containing a dithioester at the end;

[0037] Among them, the compound having a hydroxyl group at the terminal is a monohydric alcohol or a polyhydric alcohol.

[0038] The preparation method of the PVP compound containing a dithioester at the terminal provided in the second solution of the present invention is used to prepare the PVP compound containing a dithioester at the terminal provided in the first solution of the present invention.

[0039] Specifically, c...

Embodiment 1

[0080] The preparation of the PVP compound containing dithioester at the end:

[0081]

[0082] Add ethylene glycol ((2.0g, 32.3mmol), anhydrous tetrahydrofuran (50mL) and triethylamine (10.7mL) into the reaction kettle, stir well and add α-bromoisobutyryl bromide (17.8g, 77.28mmol ), after stirring at room temperature for 12h, slowly add diluted hydrochloric acid solution (10wt%) (10mL).The organic phase was washed with aqueous sodium bicarbonate solution (5wt%), and then concentrated to obtain the crude product after drying over anhydrous magnesium sulfate, and the crude product was washed with methanol Recrystallize twice to obtain EG-Br.

[0083] Weigh EG-Br (0.72g, 2mmol), potassium ethyl xanthate (1.92g, 12mmol) and absolute ethanol (20mL) in a reaction flask, and stir the reaction at room temperature for 16h. Filtration, after the filtrate was diluted with dichloromethane, washed three times with deionized water (50mL), the organic phase was dried and concentrated c...

Embodiment 2

[0089] The preparation of the PVP compound containing dithioester at the end:

[0090] Referring to the synthetic route of the PVP compound with dithioester at the end of the linear structure provided in Example 1, the molar ratio of EG-CTA to N-vinylpyrrolidone is selected as 1:400, and the dithioester at the end of the linear structure is synthesized PVP compound (L-PVP) (n=200).

[0091] Preparation of topological polymers:

[0092] In the reaction bottle, add the PVP compound (L-PVP) (n=200) (13.45g, 0.3mmol) containing dithioester at the end of the linear structure, azobisisobutylcyanide (AIBN) (16.4mg, 0.3mmol ), a polymerizable catechol monomer DMA (5.10 g, 24.6 mmol) and dimethylformamide (20 mL), reacted at 60 ° C for 6 h under the protection of argon. The reaction system was lowered to room temperature, precipitated in diethyl ether, filtered, the precipitate was washed twice with hot methanol, and the obtained solid was vacuum-dried to obtain a topological polymer...

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Abstract

The invention discloses a PVP compound with a terminal containing dithioester, a topological polymer, and preparation methods for the PVP compound with the terminal containing the dithioester and thetopological polymer. The PVP compound with the terminal containing the dithioester has a structure as shown in a formula which is described in the specification. In the formula, R1 is a substituted ester group; R2 is selected from the group consisting of C1-C6 alkyl groups; and n is in a range of 50-200. The PVP block in the PVP compound with the terminal containing the dithioester provided by theinvention enables the PVP compound to show excellent biocompatibility, hydrophilicity, stability and antifouling property; the topological polymer provided by the invention is obtained by a reactionbetween the PVP compound with the terminal containing the dithioester and a polymerizable catechol monomer, has excellent adhesion capacity with the surface of a base material, and can be used as an antifouling material.

Description

technical field [0001] The invention relates to the technical field of synthesis of antifouling compounds, in particular to a PVP compound containing a dithioester at the end, a topological polymer and a preparation method thereof. Background technique [0002] Hydrophilic polymers are often used as materials that resist adhesion of proteins and marine organisms. Among them, polyethylene glycol (PEG) is the most in-depth research and the most widely used non-ionic hydrophilic substance with anti-adhesion to proteins and marine organisms. Take the anti-protein adhesion mechanism of PEG materials as an example to illustrate: during the process of protein adsorption to the substrate surface, the protein compresses the PEG chain to generate a repulsive elasticity, which makes it difficult for the protein to approach the substrate; Hydrogen-bonded water molecules are squeezed out during the compression process, resulting in thermodynamic instability and osmotic pressure, which w...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F126/10C08F293/00C08F220/58C09D153/00C09D139/06C09D5/16
CPCC08F126/10C08F293/00C08F220/58C09D153/00C09D139/06C09D5/1662C09D5/1668
Inventor 万晓波穆有炳
Owner JIANGHAN UNIVERSITY
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