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Method for preparing hyperbranched polymer by adopting consecutive click chemical reaction

A technology of hyperbranched polymer and click chemistry, which is applied in the field of synthesizing hyperbranched polymers containing thioether and alkynyl groups, can solve the problems that monomers cannot be purchased commercially, lengthy preparation time, low comprehensive yield, etc. Wide range of monomers, wide application prospects, high yield effect

Active Publication Date: 2011-08-17
杭州德烯科技集团有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although great progress has been made, there are still bottlenecks that need to be broken through: 1. The reported monomer coupling strategy enables the synthesis of hyperbranched polymers using commercial asymmetric monomers through traditional polycondensation methods, which represents a new step in the synthesis of A major advance in strategy, but still suffers from lengthy preparation times (often several days) (Gao et al., Prog. Polym. Sci. 2004, 29 , 183); 2. It has been reported that a single click chemistry reaction can be achieved by using AB 2 or A 2 +B 3 However, there are still some methodological problems, such as: the monomers used cannot be purchased commercially, the synthesis is cumbersome and the overall yield is low (Perrier et al. J. Am. Chem. Soc. 2009, 131 , 18075), easy gel, etc.

Method used

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  • Method for preparing hyperbranched polymer by adopting consecutive click chemical reaction
  • Method for preparing hyperbranched polymer by adopting consecutive click chemical reaction
  • Method for preparing hyperbranched polymer by adopting consecutive click chemical reaction

Examples

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Embodiment 1

[0015] Step 1), under nitrogen protection, 3,6-dioxa-1,8-octanedithiol (3.64 g, 20 mmol), methanol (6.4 g, 200 mmol), KOH ( 1.12 g, 20 mmol), propargyl bromide (2.41 g, 20.4 mmol), at 15 o Reaction at C for 0.5 hour, filtered to remove the generated KBr salt precipitate, evaporated under reduced pressure to remove methanol;

[0016] Step 2), under nitrogen protection, dissolve the product obtained in step 1) in 40 mL of toluene, add 2 mol% of photosensitive free radical initiator benzoin dimethyl ether (102.5 mg), irradiate with ultraviolet light, and polymerize for 5 hours , through methanol precipitation, separation and drying to obtain a hyperbranched polymer (the number average molecular weight is 7800; the weight average molecular weight is 150000; the degree of branching is 0.44).

Embodiment 2

[0018] Step 1), under nitrogen protection, 3,6-dioxa-1,8-octanedithiol (3.64 g, 20 mmol), methanol (6.4 g, 200 mmol), KOH ( 1.01 g, 18 mmol), propargyl bromide (2.12 g, 18 mmol), at -20 o Reaction at C for 5 hours, filtered to remove the generated KBr salt precipitate, evaporated under reduced pressure to remove methanol;

[0019] Step 2), under nitrogen protection, dissolve the product obtained in step 1) in 40 mL of toluene, add 2 mol% of photosensitive free radical initiator benzoin dimethyl ether (102.5 mg), irradiate with ultraviolet light, and polymerize for 5 hours , the hyperbranched polymer was obtained by methanol precipitation, separation and drying.

Embodiment 3

[0021] Step 1), under nitrogen protection, 3,6-dioxa-1,8-octanedithiol (3.64 g, 20 mmol), methanol (0.32 g, 10 mmol), KOH ( 1.23 g, 22 mmol), propargyl bromide (2.60 g, 22 mmol), at 30 o Reaction at C for 0.5 hour, filtered to remove the generated KBr salt precipitate, evaporated under reduced pressure to remove methanol;

[0022] Step 2), under nitrogen protection, dissolve the product obtained in step 1) in 40 mL of toluene, add 2 mol% of photosensitive free radical initiator benzoin dimethyl ether (102.5 mg), irradiate with ultraviolet light, and polymerize for 5 hours , the hyperbranched polymer was obtained by methanol precipitation, separation and drying.

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Abstract

The invention discloses a method for preparing a hyperbranched polymer by adopting consecutive click chemical reaction, comprising the following steps: (1) adding 1 mole of dithiol compound, 0.5-10 moles of solvent, and 0.9-1.1 moles of base and 0.9-1.1 moles of compound containing alkynyl and halogen into a reactor in sequence in the presence of nitrogen to carry out sulfydryl-halogen reaction for 0.5-5 hours between minus 20 DEG C and 30 DEG C, filtering and removing generated precipitates, and carrying out decompressing evaporation to remove the solvent; (2) dissolving the products of reaction, which are obtained in the step (1), into 0.25-10 moles of solvent in the presence of nitrogen, adding 0.005-0.05 mole of photosensitive free radical initiator or thermosensitive free radical initiator, irradiating with ultraviolet light or heating at 40-90 DEG C to generate free radicals, carrying out sulfydryl-halogen reaction for 0.5-24 hours, precipitating, separating and drying to obtain the hyperbranched polymer. The method ensures that the tedious AB2 monomer synthesis and purification step is omitted, is fast and efficient and is simple in process. The prepared hyperbranched polymer containing a large number of thioether bonds and alkynyls has a wide application prospect in the fields of high-performance materials, additives and the like.

Description

technical field [0001] The invention relates to a method for continuously click-chemically preparing hyperbranched polymers, in particular to a method for synthesizing hyperbranched polymers containing thioether and alkynyl groups. Background technique [0002] Hyperbranched polymers (Hyperbranched polymers) are a class of highly branched macromolecules with a three-dimensional ellipsoidal structure, which is a subclass of branched polymers, and its research began in the 1980s. Compared with linear polymers, it has many unique properties, such as: high solubility, low viscosity, internal branched backbone, internal cavity, binding sites, a large number of terminal functional groups, etc. Compared with another large class of highly branched polymers, dendrimers, its molecular design is more variable and its synthesis method is simpler. Hyperbranched polymers have been widely used in coatings, processing aids, pharmaceutical carriers, metal nanocatalyst templates and other fi...

Claims

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Application Information

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IPC IPC(8): C08G75/04C08G75/045
Inventor 高超韩金
Owner 杭州德烯科技集团有限公司
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