Novel method for preparing polymer on basis of carbon free radical coupling reaction

A coupling reaction and polymer technology, which is applied in the field of polymer preparation, can solve the problem that the polymer is not characterized in detail, and achieve the effects of variable structure, convenient synthesis and simple synthesis conditions.

Active Publication Date: 2016-04-06
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Yagci et al. reported that using dibromo-p-xylene as a monomer to prepare parylene by free radical coupling reaction, but the polymer was not characterized in detail (Designed Monomers and Polymerization, 2007, 10, 575)

Method used

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  • Novel method for preparing polymer on basis of carbon free radical coupling reaction
  • Novel method for preparing polymer on basis of carbon free radical coupling reaction
  • Novel method for preparing polymer on basis of carbon free radical coupling reaction

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]

[0034] Table 1 Different dibromo compound monomers and their abbreviations

[0035] monomer abbreviation

monomer name

R 1

R 2

R 3

A

1,4-bis(1-bromoethyl)benzene

-

-

-

B1

Methyl 2,5-Dibromomethylbenzoate

-CH 3

-

-

B2

2,5-Dibromomethylbenzoic acid ethyl ester

-C 2 h 5

-

-

B3

Propyl 2,5-Dibromomethylbenzoate

-C 3 h 7

-

-

B4

2,5-Dibromomethylbenzoic acid isopropyl ester

-iso-C 3 h 7

-

-

B5

Butyl 2,5-dibromomethylbenzoate

-C 4 h 9

-

-

B6

2,5-Dibromomethylbenzoic acid isobutyl ester

-iso-C 4 h 9

C

Bis(4-bromomethylphenyl) ether

...

Embodiment 1

[0042] The synthesis of embodiment 1TPMA

[0043] 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 2solution, 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. Continue to recrystallize 3 times to obtain pale yellow needle-like crystals, yield 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

[0044] The synthesis of embodiment 2 monomer A

[0045] 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 the field of preparation methods of polymers and aims to provide a novel method for preparing a polymer on the basis of a carbon free radical coupling reaction. The novel method for preparing the polymer on the basis of the carbon free radical coupling reaction comprises steps as follows: a dibromide compound, copper and polyamine ae added to a reactor, a deoxidized solvent is added after deoxidization, a product is obtained through a reaction, then the product passes through a neutral alumina column firstly and then is subjected to reduced pressure distillation for removal of an eluting agent added during column passing or addition of a precipitant, and the required polymer is obtained. The synthesis condition is simple, the dibromide compound is convenient to synthesize, the structure is changeable, and the method is a novel convenient and efficient polymer synthesis method; polyaromatic hydrocarbon, polyester, polyether, polysulfone and the like which adopt novel structures can be prepared with the method.

Description

technical field [0001] The invention relates to the field of polymer preparation methods, in particular to a new method for preparing polymers based on carbon free radical 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 field of polymer synthe...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/02C08G61/12
CPCC08G61/02C08G61/121C08G2261/11C08G2261/3424C08G2261/344
Inventor 王齐刘喆
Owner ZHEJIANG UNIV
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