Novel method for preparing copolymer based on co-coupling reaction of two different kinds of carbon free radicals

A coupling reaction and free radical technology, applied in the field of polymer preparation, to achieve the effect of simple synthesis conditions, convenient synthesis, and variable structure

Active Publication Date: 2016-04-20
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are few reports on the preparation of polymers from small molecules by free radical coupling reaction

Method used

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  • Novel method for preparing copolymer based on co-coupling reaction of two different kinds of carbon free radicals
  • Novel method for preparing copolymer based on co-coupling reaction of two different kinds of carbon free radicals
  • Novel method for preparing copolymer based on co-coupling reaction of two different kinds of carbon free radicals

Examples

Experimental program
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Effect test

preparation example Construction

[0031] (1) Preparation of monomer

[0032] All dibromo monomers can be prepared by existing common synthesis methods, and the molecular structures of the dibromo compounds used in the examples are shown in Table 1 below.

[0033] The molecular structural formulas of eight kinds of dibromocompounds A, B, C, D, E, F, G, H are as follows respectively:

[0034]

[0035] Table 1 Different dibromo compound monomers and their abbreviations

[0036] monomer abbreviation

monomer name

A

1,4-bis(1-bromoethyl)benzene

B

1,4-Dibromomethylbenzene

C

1,3-Dibromomethyl-2-fluorobenzene

D

Methyl 2,5-Dibromomethylbenzoate

E

Methyl 3,5-Dibromomethylbenzoate

F

Bis(4-bromomethylphenyl) ether

G

Bis(4-bromomethylphenyl)sulfone

H

1,4-bis(1-bromo-1-methylethyl)benzene

[0037] (2) Polymerization method

[0038] The measured two kinds of dibromo compounds and ligands, copper powder (also can be...

Embodiment 1

[0043] The synthesis of embodiment 1TPMA

[0044] Dissolve 16.4g of 2-chloromethylpyridine hydrochloride in 40mL of deionized water, cool in an ice bath, slowly add 20mL of 5M NaOH aqueous solution, and the solution turns pink. Add 80 mL of CH containing 5.4 g of 2-(aminomethyl)pyridine 2 Cl 2 solution, warmed to room temperature. Add 20 mL of 5M NaOH aqueous solution with a micro-syringe, and drop it in 50 hours. Stop the reaction, wash the organic phase with 3×10mL15% NaOH aqueous solution, combine the organic phases, anhydrous MgSO 4 Dry, filter and concentrate. The product was extracted with diethyl ether in a boiling state, the insoluble matter was removed, cooled, the product was crystallized in diethyl ether, and filtered. The recrystallization was continued for 3 times to obtain pale yellow needle crystals with a yield of 37%. 1 HNMR (400MHz, CDCl 3 ): 8.54-8.53 (d, 3H), 7.67-7.64 (t, 3H), 7.60-7.58 (d, 3H), 7.16-7.13 (t, 3H), 3.89 (s, 6H).

Embodiment 2

[0045] The synthesis of embodiment 2 monomer A

[0046] Add 11.7g of N-bromosuccinimide, 0.3g of benzoyl peroxide, 4.7mL of 1,4-diethylbenzene, and 50mL of carbon tetrachloride into a 100mL three-necked flask in turn, blow nitrogen gas for 10 minutes, and reflux for 1.5 hours . Stop the reaction, filter, and concentrate the filtrate to obtain a light yellow solid. The crude product was recrystallized from n-hexane to obtain white crystals, which were dried in vacuo with a yield of 60%. 1 HNMR (400MHz, CDCl 3 ): 7.41 (s, 4H, ArH), 5.22-5.17 (q, 2H, 2CHBrCH 3 ), 2.04-2.03 (d, 6H, 2CHBrCH 3 ). Elemental analysis results: theoretical value (%): C, 41.13; H, 4.14; measured value (%): C, 40.97; H, 4.12.

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Abstract

The invention relates to a preparation method of a polymer, and provides a novel method for preparing a copolymer based on a co-coupling reaction of two different kinds of carbon free radicals. The novel method for preparing the copolymer based on the co-coupling reaction of the two different kinds of carbon free radicals comprises the steps that the mixture of two kinds of dibromo compounds, copper and polyamine are added into a reactor, a deoxy solvent is added after deoxidation, a reaction is carried out at 20-80 DEG C for 1-4 h, then unreacted copper and copper complex are removed, and therefore the needed polymer is obtained. The method is the novel polymer synthesis method which is convenient to implement and efficient, the synthesis condition is simple, the dibromo compounds are convenient to synthesize, the structure is variable, and polyaromatic hydrocarbon, polyester, polyether, polysulfone and the like of the novel structure can be prepared.

Description

technical field [0001] The invention relates to the field of polymer preparation methods, in particular to a new method for preparing copolymers based on two different carbon free radical co-coupling reactions. Background technique [0002] Although free radical addition reaction has been widely used in polymer synthesis, another efficient reaction in free radical reaction—coupling reaction is rarely used in polymer synthesis. This is because, in addition to coupling reactions, free radicals can also undergo side reactions such as disproportionation reactions and chain transfer reactions. In addition, due to the non-selectivity of the reaction between free radicals, there are many kinds of products. Therefore, the coupling reaction can be applied to the synthesis of polymers by suppressing other side reactions of free radicals, expanding the field of polymer synthesis methodology. Due to the high reactivity of free radicals, this reaction has certain advantages in the fiel...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/02C08G61/12
CPCC08G61/02C08G61/025C08G61/121C08G2261/312C08G2261/334C08G2261/41
Inventor 王齐刘喆
Owner ZHEJIANG UNIV
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