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Method for preparing polytriazole through catalysis of recyclable supported cuprous catalyst and prepared polytriazole

A copper catalyst, supported technology, applied in the field of polymer preparation, can solve problems such as the influence of photoelectric properties of polymers, and achieve the effects of improving photoelectric properties, increasing contact area, and high economic benefits

Inactive Publication Date: 2013-11-27
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, if it is not removed, the catalyst residue will have a great impact on the photoelectric properties of the polymer. If it is used in the biomedical field, copper also has strong biological toxicity (Toxicology2003, 189, 147). Therefore, it is necessary to reduce the amount of copper in the polymer. Residues appear to be necessary

Method used

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  • Method for preparing polytriazole through catalysis of recyclable supported cuprous catalyst and prepared polytriazole
  • Method for preparing polytriazole through catalysis of recyclable supported cuprous catalyst and prepared polytriazole
  • Method for preparing polytriazole through catalysis of recyclable supported cuprous catalyst and prepared polytriazole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment approach

[0052] 1, Drying of A-21

[0053] Weigh 20g of wet commercially available A-21 resin (CAS No.: 9049-93-8), soaked in 100mL methanol for 0.5h, filtered, and repeated three times. The same method was used to wash three times with dichloromethane, and the obtained resin particles were dried overnight in a vacuum oven. Finally, light yellow spherical A-21 resin pellets.

[0054] 2. Preparation of supported click polymerization catalyst

[0055] Weigh 2.0g dry Add A-21 resin, 190mg CuI, into a 100mL single-necked bottle, add 30mL of degassed acetonitrile, and gently stir at room temperature for 17h under the protection of nitrogen. Acetonitrile was filtered off, followed by washing twice with 15 mL of acetonitrile and dichloromethane, and drying to obtain light green resin particles.

[0056] 3. Synthesis of azide and alkyne monomers

[0057] The synthesis methods of several first monomers and second monomers selected by the present invention are based on the applicant'...

Embodiment 1

[0061] The supported catalyst catalyzes the click polymerization of azide and alkyne to synthesize polymer P1:

[0062] Alkyne monomer 1a (18.6 mg, 0.1 mmol), azide monomer 2a (47.9 mg, 0.1 mmol) and 15.0 mg CuIA-21 supported catalyst were added to a 10 mL polymerization tube. After evacuating and filling with nitrogen for 3 times, 1.0 mL of tetrahydrofuran was injected, and after the monomers were completely dissolved, the temperature was raised to 60°C for 8 hours of reaction. The reaction mother liquor was diluted with 5 mL of chloroform, filtered and added dropwise to 200 mL of rapidly stirring n-hexane to obtain a white flocculent precipitate. Stand overnight, filter, and dry to obtain 57.2 mg of polymer (yield: 86.1%) and copper content of 180 ppm. The weight average molecular weight was 45500, and the molecular weight distribution was 1.81. IR(KBr),ν(cm -1 ):2938,2094,1506,1232,829,575. 1 H NMR (400MHz, CDCl 3 ):δ(TMS,ppm):7.66,7.12,6.93,6.78,5.15,4.37,3.91,1.95,1....

Embodiment 2

[0068] CuI-Catalyzed Click Polymerization of Azides and Alkynes to Synthesize Polymer P1

[0069] Alkyne monomer 1a (18.6 mg, 0.1 mmol), azide monomer 2a (47.9 mg, 0.1 mmol) and 0.76 mg CuI were added to a 10 mL polymerization tube. After evacuating and filling with nitrogen for 3 times, inject 1.0 mL of N,N-dimethylformamide, and after the monomers are completely dissolved, raise the temperature to 60°C for 8 hours to react. The reaction mother liquor was diluted with 5 mL of chloroform, filtered and added dropwise into 200 mL of rapidly stirring n-hexane to obtain a brown flocculent precipitate. Stand overnight, filter and dry to obtain 52.5 mg of polymer (yield 79.0%) and copper content 4282 ppm. The weight average molecular weight was 33700, and the molecular weight distribution was 1.86. Other characterization results are the same as in Example 1.

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Abstract

The invention discloses a method for preparing polytriazole through catalysis of a recyclable supported cuprous catalyst and prepared polytriazole. The method comprises the following steps: under the catalysis of a supported click polymerization catalyst, a nitrine monomer and an alkyne monomer are subjected to click polymerization reaction in an organic solvent so as to form polytriazole. The method realizes the click polymerization reaction through catalysis of the supported cuprous catalyst, and has the advantages that the activity is high, the condition is gentle, the stereoselectivity is high, and the solubility of polymer is excellent, and the copper content of the polymer prepared by utilizing the reaction is low. In addition, after the supported cuprous catalyst used by the reaction is recycled for 4 times, the reaction activity of the supported cuprous catalyst is not subjected to obvious change.

Description

technical field [0001] The invention belongs to the field of polymer preparation, and in particular relates to a method for preparing polytriazole catalyzed by a recyclable supported monovalent copper catalyst and the prepared polytriazole. Background technique [0002] In 2001, the American chemist Sharpless proposed the concept of "click chemistry", which refers to a class of chemical reactions with the advantages of high efficiency, good stereoselectivity, mild reaction conditions, and simple product separation and operation (Angew.Chem.Int.Ed. .2001, 40, 2004). In 2002, the Meldal of Denmark and the Sharpless research group of the United States independently discovered that monovalent copper can catalyze the cycloaddition reaction of azide and terminal alkyne (J.Org.Chem.2002, 67, 3057; Angew.Chem.Int. Ed. 2011, 40, 2004). Since the alkyne and azide groups are relatively easy to introduce into the desired monomer structure, and the reaction conditions are mild, the fun...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G73/08
CPCY02P20/584
Inventor 吴海强秦安军唐本忠孙景志
Owner ZHEJIANG UNIV
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