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Polymer synthesis method using carbon-carbon double bond construction

A synthesis method and technology of carbon double bonds, applied in the field of polymer preparation, can solve problems such as harsh reaction conditions, and achieve the effects of mild synthesis conditions, convenient synthesis, and variable structure

Active Publication Date: 2017-03-15
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The method of preparing polymers by constructing carbon-carbon double bonds in the above scheme is limited to the use of diazoacetyl compound monomers, which are dangerous and have harsh reaction conditions

Method used

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  • Polymer synthesis method using carbon-carbon double bond construction
  • Polymer synthesis method using carbon-carbon double bond construction
  • Polymer synthesis method using carbon-carbon double bond construction

Examples

Experimental program
Comparison scheme
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preparation example Construction

[0035] (1) Preparation of monomer

[0036] All bis-dibromo monomers can be prepared by the existing common synthetic methods. The molecular structures of bis-dibromo compounds used in the examples are shown in the following and Table 1.

[0037]

[0038] Table 1 Different dibromo compound monomers and their abbreviations

[0039] Monomer abbreviation Monomer name A1

1,4-bis(dibromomethyl)benzene A2

Ethyl 2,5-bis(dibromomethyl)benzoate A3

2,5-bis(dibromomethyl)phenol acetate A4

2,5-bis(dibromomethyl)phenylhexyl ether B1

2,5-Dihexyloxy-1,4-bis(dibromomethyl)benzene B2

2,5-Dioctyloxy-1,4-bis(dibromomethyl)benzene C1

1,4-bis(dibromoethyl)benzene D1

3,5-bis(dibromomethyl)anisole D2

3,5-bis(dibromomethyl)tert-butylbenzene D3

Ethyl 3,5-bis(dibromomethyl)benzoate E1

2,2-bis(4-dibromomethylphenyl)hexafluoropropane E2

4,4’-Bis(dibromomethyl)phenyl ketone E3

4,4’-Bis(dibromomethyl)phenylsulfone

[0040] (2) Polymerization method

[0041] Deoxidize a certain stoichiometric ratio of bis-dibrom...

Embodiment 1

[0046] Example 1 Synthesis of TPMA

[0047] 16.4g of 2-chloromethylpyridine hydrochloride was dissolved in 40mL of deionized water, cooled in an ice bath, and 20mL of 5M NaOH aqueous solution was slowly added, and the solution turned pink. Add 80mL CH containing 5.4g 2-(aminomethyl)pyridine 2 Cl 2 The solution was warmed to room temperature. Use a micro syringe to add 20 mL of 5M NaOH aqueous solution, and drop it in 50 hours. Stop the reaction, wash the organic phase with 3×10 mL 15% NaOH aqueous solution, combine the organic phases, anhydrous MgSO 4 Dry, filter, and concentrate. Extract the product with ether under boiling state, remove insoluble matter, cool, crystallize the product in ether, and filter. Continue recrystallization 3 times to obtain pale yellow needle-like crystals with a yield of 37%. 1 H NMR(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

[0048] Example 2 Monomer A 1 Synthesis

[0049] 11.7 g of N-bromosuccinimide, 0.3 g of benzoyl peroxide, 4.7 mL of p-xylene, and 50 mL of carbon tetrachloride were sequentially added to a 100 mL three-necked flask, and nitrogen was bubbled for 10 minutes, and refluxed for 1.5 hours. The reaction was stopped, filtered, and the filtrate was concentrated to obtain a pale yellow solid. The crude product was recrystallized with n-hexane to obtain white crystals, which were dried in vacuum with a yield of 60%. 1 H NMR(400MHz, CDCl 3 ):

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Abstract

The invention relates to preparation of polymers and provides a polymer synthesis method using carbon-carbon double bond construction. The method comprises injecting a deoxygenated solvent into a reactor, adding a compound containing double alpha, alpha-dihalo functional groups as monomers, copper and polyamine into the reactor, stirring the materials, carrying out deoxygenation, carrying out polymerization based on carbon-carbon double bond formation at a temperature of 0-60 DEG C for 0.25-12h under conditions of a monomer molar concentration of 0.01-0.1M and a mole ratio of the monomer, copper to polyamine of 1: 1: 1 to 1: 3: 3, and carrying out separation and purification to remove the unreacted copper and copper complex so that a carbon-carbon double bond-containing polymer is obtained. The method has the advantages of mild synthesis conditions, convenient synthesis of a dibromo-compound and product structure controllability. The method is a convenient and efficient novel method for synthesizing a polymer with a carbon-carbon double bond in a main chain. The method can prepare a polyaromatic hydrocarbon with a novel structure and can produce a main chain-conjugated polymer with photoelectric functions under relatively mild conditions.

Description

Technical field [0001] The invention relates to the field of preparation methods of polymers, and particularly relates to a new method for preparing polymers by the construction of carbon-carbon double bonds. Background technique [0002] The preparation of polymers from small molecule monomers is a process of forming new chemical bonds between monomers. So far, the chemical bonds formed in the polymerization process are mainly single bonds. For example, the addition reaction of olefins forms a new carbon-carbon single bond; the condensation polymerization of acid alcohol forms a new carbon-oxygen single bond. The synthesis methods of polymers are constantly enriched and developed, but the method of forming polymers through the construction of double bonds is rarely reported. [0003] [0004] Earlier literature reported the polymerization of α,α-dibromotoluene in the presence of metallic magnesium, and a polymer with an average molecular weight of less than 1100g / mol was obtained...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/02
CPCC08G61/02C08G2261/11C08G2261/3422
Inventor 曹花王齐
Owner ZHEJIANG UNIV
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