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Ring-opening polymerization method of cyclic monomer

A cyclic monomer, ring-opening polymerization technology, applied in the field of green catalytic synthesis, can solve the problems of difficult preparation of metal catalysts and enzyme catalysts, inability to adapt to new requirements, unfavorable material stability, etc., and achieve narrow molecular weight distribution index, wide range, The effect of high product yield

Active Publication Date: 2020-08-28
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the product has a low molecular weight and a wide molecular weight distribution, which is not conducive to the stability of the material
And with the increasing demand for medical materials and nanomaterials, the quality and performance requirements of materials have been improved, and the shortcomings of metal residues in metal catalysts and difficult preparation of enzyme catalysts have been unable to meet the new requirements.

Method used

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  • Ring-opening polymerization method of cyclic monomer
  • Ring-opening polymerization method of cyclic monomer
  • Ring-opening polymerization method of cyclic monomer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0078] The preparation of carbocation Lewis acid 18, under the protection of anhydrous inert gas, 2.8g (15.4mmol) benzophenone, 23.1ml (in tetrahydrofuran, substance concentration is 1mol / L) phenylmagnesium bromide, use Anhydrous tetrahydrofuran was used as a solvent, and reacted at 60 degrees Celsius. After 2 hours of reaction, the reaction was complete, and 0.54ml (30mmol) of water was added to quench the reaction. After rotary evaporation, drying and recrystallization, 2.5g of triphenylmethanol was obtained. 62.5%. Dissolve 2.5g (9.6mmol) triphenylmethanol in anhydrous ether, cool down to 0°C, add 2.1ml (14.4mmol) tetrafluoroborate diethyl ether dicomplex dropwise to the reaction, and a yellow solid precipitates out immediately. After filtration and drying, 2.7g carbocation Lewis acid 18 was obtained, and its hydrogen spectrum structure was as follows: figure 1 shown.

[0079] In a 10mL polymerization tube, add δ-valerolactone (0.27ml, 3mmol), carbocation Lewis acid 18 (0...

Embodiment 2

[0081] Carbocation Lewis acid 18 was prepared as in Example 1.

[0082] In a 10mL polymerization tube, add ε-caprolactone (0.33ml, 3mmol), carbocation Lewis acid 18 (0.033g, 0.1mmol), triphenylamine (0.0245g, 0.1mmol), benzyl alcohol (10.3μL, 0.1mmol), finally add 1mL of dichloromethane as a solvent, stir magnetically for 2.5 hours at 30°C, stop the reaction, slowly drop the resulting solution into cold methanol, a white polymer precipitates, centrifuge and vacuum dry to obtain snow-white Product 0.32g, transformation efficiency 95%, the number average molecular weight M of polycaprolactone n It is 3.4kg / mol, and the molecular weight distribution PDI is 1.10. The hydrogen spectrum of the product is as Figure 4 As shown, the size exclusion chromatography of the product is shown as Figure 5 shown.

Embodiment 3

[0084] Carbocation Lewis acid 18 was prepared as in Example 1.

[0085] In a 10 mL polymerization tube, add trimethylene carbonate (0.3063 g, 3 mmol), carbocation Lewis acid 18 (0.033 g, 0.1 mmol), triphenylamine (0.0245 g, 0.1 mmol), benzyl alcohol (10.3 μL, 0.1mmol), finally add 1mL of toluene as a solvent, stir magnetically for 2.5 hours at 60°C, stop the reaction, slowly drop the resulting solution into cold methanol, and a colorless and transparent oily substance precipitates out. After centrifugation and vacuum drying, a colorless and transparent viscous Thick thing 0.29g, transformation rate is 95%, the number average molecular weight M of polytrimethylene carbonate n It was 3.2 kg / mol, and the molecular weight distribution PDI was 1.15.

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Abstract

The invention belongs to the field of organic synthesis, and particularly relates to a ring-opening polymerization method of a cyclic monomer, which adopts the specific scheme that ring-opening polymerization of the cyclic monomer is catalyzed by Lewis acid-base pairs in the presence of an initiator. Lewis acid-base pairs are used as a catalyst; on one hand, the range of the ring-opening polymerization catalyst is expanded; on the other hand, compared with a strong acid or strong alkali catalyst reported before, the catalyst has the characteristics of high catalytic efficiency and mildness, and the catalytic system activates the monomer and activates the initiator or chain end at the same time through a bifunctional activation mechanism, and has the characteristic of high efficiency compared with a reported monomer activation mechanism or chain end activation mechanism. By adopting the catalyst, the polyester product with the target molecular weight can be synthesized in a controlled manner as required, the molecular weight distribution index is relatively narrow, the product yield is high, the product conversion rate is high, and no monomer or metal residue exists.

Description

technical field [0001] The invention belongs to the technical field of green catalytic synthesis, and in particular relates to a method for ring-opening polymerization of cyclic monomers. Background technique [0002] Biodegradable polymer materials can be divided into natural polymer materials and synthetic polymer materials according to their sources. Among them, natural polymer materials mainly include polysaccharides and proteins, including natural polymers such as chitin, hyaluronic acid, collagen, fibrin, etc., which can be obtained directly from organisms and have a wide range of sources; synthetic polymer materials include biosynthetic materials and Two categories of chemically synthesized materials. Compared with natural polymer materials, synthetic polymer materials can be physically and chemically modified according to the application field of the material, so that the properties of the material and the application are more consistent. [0003] Among many synthe...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G63/87C08G63/84C08G63/08C08G64/30C08G65/04
CPCC08G63/87C08G63/84C08G63/823C08G63/08C08G64/30C08G65/04C08G64/0208C08G64/305C08G65/2609C08G65/18C08G65/2672C08G65/2654C08G2230/00
Inventor 郭凯姚志威李振江张婵朱玥嘉张磊罗子堃
Owner NANJING UNIV OF TECH
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