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Structure, synthesis and use of 2-ethyle-2-allyloxymethyl-1,3-propylene carbonate

A technology of propylene glycol carbonate and allyloxymethyl, which is applied in the field of biomedical polymers, can solve the problems of residual protective group, low yield, affecting the application of polymers, etc., and achieves the effects of high application value and simple preparation method.

Inactive Publication Date: 2015-07-01
CHANGZHOU HIGH TECH RES INST OF NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the existence of the protective groups on these side groups, the synthesis of monomers is difficult, the yield is low, and the polymerization activity of cyclic monomers is affected, and even the polymerization reaction cannot be carried out.
In addition, the subsequent polymer deprotection reaction is not easy to carry out completely, often resulting in the residue of the protecting group, which affects the application of the polymer.

Method used

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  • Structure, synthesis and use of 2-ethyle-2-allyloxymethyl-1,3-propylene carbonate
  • Structure, synthesis and use of 2-ethyle-2-allyloxymethyl-1,3-propylene carbonate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Compound of Example 1 b : 2,2-Dimethyl-5-ethyl-5-hydroxymethyl-[1,3]-dioxane

[0021] Add trimethylolpropane to a 500 mL three-necked round bottom flask equipped with a condenser and a mechanical stirrer a (67.09g, 0.5mol) and acetone 400mL. After the trimethylolpropane was completely dissolved, 0.5 g of p-toluenesulfonic acid was added to the system, followed by stirring and reacting at room temperature for 16 hours. Then 1 g of potassium carbonate was added, and after stirring at room temperature for 1 hour, excess acetone was recovered by rotary evaporation. The resulting mixture was distilled under reduced pressure at 5mmHg / 110-112°C to obtain the ketal compound b A total of 68g, yield 78%. 1 H NMR (CDCl 3 , 300MHz), δ: 0.8 (t, C H 3 CH 2 , 3H), 1.25 (q, CH 3 C H 2 ,2H), 1.39 (s, CCH 3 , 3H), 1.43 (s, CCH 3 , 3H), 1.72 (br, OH, 1H), 3.66 (s, C H 2 O, 2H), 3.67 (s, C H 2 O, 2H), 3.76 (d,C H 2 OH,2H).

Embodiment 2

[0022] Compound of Example 2 c : 2,2-Dimethyl-5-ethyl-5-allyloxy-[1,3]-dioxane

[0023] In a 500mL three-necked round bottom flask equipped with a condenser, a constant pressure dropping funnel and a mechanical stirrer, add the ketal compound in sequence b (61g, 0.35mol), tetrabutylammonium bisulfate (11.9g, 0.035mol) and 300ml of 50wt% NaOH solution. The reaction solution was cooled to 0°C, and allyl chloride (107.1 g, 1.14 mol) was slowly added dropwise to the stirring reaction mixture. Thereafter, the reaction solution was heated to 40° C., stirred for 18 hours, and cooled to room temperature after the reaction. Subsequently, 300 mL of dichloromethane was added, allowed to stand, and the organic phase was separated and washed three times with distilled water, and dried over magnesium sulfate. Then, the desiccant was filtered off, dichloromethane and excess allyl chloride were recovered by rotary evaporation, and the residue obtained was subjected to vacuum distillati...

Embodiment 3

[0024]Example 3 compound d : 2-Ethyl-2-allyloxymethyl-1,3-propanediol

[0025] In a 500mL three-neck round bottom flask equipped with a condenser and a mechanical stirrer, the compounds were added sequentially c (64.3g, 0.3mol), methanol 200mL and 1mol / L hydrochloric acid 200mL, heated up to 40°C, and stirred for 24 hours. After the reaction, the reaction solution was concentrated by rotary evaporation, and the residue was dissolved in 100 mL of ether, washed with distilled water until neutral, and dried over magnesium sulfate. The resulting solution was spin-dried and distilled under reduced pressure at 10mmHg / 130-131°C to obtain the diol compound d A total of 48.9g, yield 93.6%. 1 H NMR (CDCl 3 , 300 MHz), δ:0.85 (t, C H 3 CH 2 , 3H) , 1.33 (q, CH 3 C H 2 , 2H), 2.53 (br, OH, 2H), 3.46 (s, C H 2 O, 2H), 3.62 (d, C H 2 OH, 2H), 3.74 (d, C H 2 OH, 2H), 3.98 (d, C H 2 CH=CH 2 , 2H), 5.24 (m, CH=C H 2 , 2H), 5.89 (m, H C=CH 2 , 1H).

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PUM

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Abstract

The invention discloses a structure, use and synthesis method of 2-ethyle-2-allyloxymethyl-1,3-propylene carbonate monomer. The synthesis method comprises the following steps: with trimethylolpropane as raw material, firstly protecting two hydroxyls, and allyl etherizing the other hydroxyls, de-protecting to obtain glycol precursor, cyclizing to obtain a carbonate monomer containing double-bond lateral groups. The polymer prepared from the monomer can realize the physical, chemical and biological performance modification for the polycarbonate through a series of reactions such as hydrogenation, addition, cycloaddition, epoxidation and cross-linking reaction of the lateral group double bonds so as to obtain the functionalized polycarbonate to meet different requirements of biomedicine applications.

Description

Technical field [0001] The invention involves the structure, synthesis and use of 2-ethyl-2-hydrauloxymethyl-1,3-propyl carbonate monomers, which belongs to the field of biomedical polymer. Background technique [0002] Activated polycarbonate is an important type of biodegradable / absorbing polymer.It has extensive physical, chemical and biological properties, and there are many types, and the structure can be adjusted to meet different biomedical needs. On the other hand, carbonate is generated after degradation of carbon dioxide and neutral alcohol, which can avoid polymerization to avoid polymerization.Lactic acid (PLA), polyethylene acid (PGA), etc. caused by carboxylic acid substances caused by degradation process.The biochemical polycarbonate has become increasingly widely used in the aspects of absorbing surgical sutures, drug control release, implanted materials in the body, and tissue regeneration. [0003] During the degradation of ordinary polycarbonate such as polytes...

Claims

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Application Information

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IPC IPC(8): C07D319/06C08G64/30C08G64/02
CPCC07D319/06C08G64/0291C08G64/30
Inventor 冯磊王琼陈强
Owner CHANGZHOU HIGH TECH RES INST OF NANJING UNIV
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