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α-Butyl cyanoacrylate derivative and preparation method thereof

A technology of butyl cyanoacrylate and butyl cyanoacetate, which is applied in the field of α-butyl cyanoacrylate derivatives and its preparation, can solve the problems of different degradation speeds, unsatisfactory compatibility, cohesive force and fluidity Insufficient adjustment and other problems, to achieve the effect of short reaction time, cheap and easy-to-obtain catalyst, and low viscosity

Active Publication Date: 2016-03-02
GUANGZHOU BAIYUN MEDICAL ADHESIVE CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the compatibility of these regulators with medical adhesives such as α-cyanoacrylic acid is not ideal, and their degradation speeds are different, and it is difficult to participate in the polymerization of medical adhesives, so the adjustment of their adhesion and fluidity is not perfect.

Method used

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  • α-Butyl cyanoacrylate derivative and preparation method thereof
  • α-Butyl cyanoacrylate derivative and preparation method thereof
  • α-Butyl cyanoacrylate derivative and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0044] The preparation method of α-cyano-α-pentenoic acid butyl ester described in the present embodiment comprises the steps:

[0045] (1) In a 250mL two-necked flask equipped with a magnetic stirrer, add butyl cyanoacetate 35.3g (250mmol), zinc acetate dihydrate 0.68g (3mmol) and propionaldehyde 29.1g (500mmol) successively, in Stir the reaction at 60°C for 5h;

[0046] (2) Recover excess propionaldehyde under reduced pressure, then add 60mL dichloromethane, transfer the reaction solution to a 250mL separatory funnel, wash three times with 100mL brine (NaCl solution) each time, separate the organic layer, and wash with anhydrous Magnesium sulfate was dried overnight, filtered, and the filtrate was removed from the solvent with a rotary evaporator;

[0047] (3) The resulting liquid was distilled under reduced pressure, and the fraction at 105-115° C. (230 Pa) was collected to obtain 38.6 g of a colorless oily liquid with a purity of 99.2% and a yield of 84.5% (calculated as ...

Embodiment 2

[0051] The preparation method of the alpha-cyano-alpha-hexenoic acid butyl ester described in the present embodiment comprises the steps:

[0052] (1) In a 250mL two-necked flask equipped with a magnetic stirrer, add 35.3g (250mmol) of butyl cyanoacetate, 0.68g (3mmol) of zinc acetate dihydrate and 36.0g (500mmol) of butyraldehyde in turn. Stir the reaction at 60°C for 5h;

[0053] (2) Recover excess propionaldehyde under reduced pressure, then add 60mL dichloromethane, transfer the reaction solution to a 250mL separatory funnel, wash three times with 100mL brine (NaCl solution) each time, separate the organic layer, and wash with anhydrous Magnesium sulfate was dried overnight, filtered, and the filtrate was removed from the solvent with a rotary evaporator;

[0054] (3) The resulting liquid was distilled under reduced pressure, and the fraction at 105-115° C. (230 Pa) was collected to obtain 38.6 g of a colorless oily liquid with a purity of 99.2% and a yield of 84.5% (calc...

Embodiment 3

[0058] The preparation method of α-cyano-α-pentenoic acid butyl ester described in the present embodiment comprises the steps:

[0059] (1) In a three-necked flask equipped with a thermometer, reflux condenser and mechanical stirring, add 70.8g (502mmol) of butyl cyanoacetate, 1.6g (7mmol) of zinc acetate dihydrate and 30.8g (630mmol) of propionaldehyde, methanol 100mL, reflux and stir at 70±5℃ for 2h;

[0060] (2) dry overnight with anhydrous magnesium sulfate, filter, and the filtrate is desolvated with a rotary evaporator;

[0061] (3) The resulting liquid was distilled under reduced pressure, and the fraction at 110-115° C. (230 Pa) was collected to obtain 83.2 g of a colorless oily liquid with a purity of 99.4% and a yield of 90.9% (calculated as butyl cyanoacetate).

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Abstract

The invention relates to an alpha-butyl cyanoacrylate derivative and a preparation method thereof. The structure of the alpha-butyl cyanoacrylate derivative has the following general formula. The preparation method comprises: with n-butyl cyanoacetate and formaldehyde as raw materials, the alpha-butyl cyanoacrylate derivative is prepared from a condensation reaction in the presence of a catalyst by virtue of vacuum distillation. The reaction is simple to operate, high in total yield and is suitable for industrial production. The prepared alpha-butyl cyanoacrylate derivative is free of shear strength, low in viscosity, good in fluidity, and can be used as a regulator of alpha-butyl cyanoacrylate medical adhesives. The formula is shown in the specification, wherein n is equal to 1-6.

Description

technical field [0001] The invention relates to the field of biomedicine, in particular to a butyl α-cyanoacrylate derivative and a preparation method thereof. Background technique [0002] α-Cyanoacrylate medical glue was successfully developed by EastmanKodark Company of the United States in 1958 and introduced to the market. It has good biocompatibility and adhesiveness, is solvent-free, does not require heating and pressure, and has a wide range of adhesion. , high strength, instant curing, basically non-toxic. At present, this kind of medical glue has been widely used in clinical practice, mainly used for bonding and fixing, replacing sutures, rapid hemostasis, filling and plugging, etc., and solved many problems beyond the reach of traditional surgical methods. The medical glue that has been used and is being studied Adhesives can be divided into soft tissue medical adhesives, dental medical adhesives, orthopedic medical adhesives, skin pressure sensitive adhesives, e...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C255/23C07C253/30
Inventor 曾仑张雷栗雪艳李晶史志伟
Owner GUANGZHOU BAIYUN MEDICAL ADHESIVE CO LTD
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