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Terminal alkynyl containing RAFT chain transfer agent and preparation method and application thereof

A technology of chain transfer agent and terminal alkyne is applied in the field of reversible addition-fragmentation chain transfer radical polymerization chain transfer agent and its preparation, which can solve the problems of incapable of polymer modification and the like

Inactive Publication Date: 2016-07-27
FOSHAN CENT FOR FUNCTIONAL POLYMER MATERIALS & FINE CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] At present, most of the RAFT chain transfer agents do not have groups that can participate in the click reaction, and the polymer cannot be further modified by click chemistry, so it cannot be directly applied to the combination of click chemistry and RAFT polymerization to prepare polymers with specific structures and functions.

Method used

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  • Terminal alkynyl containing RAFT chain transfer agent and preparation method and application thereof
  • Terminal alkynyl containing RAFT chain transfer agent and preparation method and application thereof
  • Terminal alkynyl containing RAFT chain transfer agent and preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0032] A kind of preparation of the RAFT chain transfer agent containing terminal carboxyl group:

[0033] (1) the mass fraction is that 50% sodium hydroxide solution (4gNaOH, 0.1mol) joins in the mixed solution of tert-butyl mercaptan (9.02g, 0.1mol) and distilled water (15ml) under stirring state, then Add 5ml of acetone, continue to stir for 30min; add dropwise carbon disulfide (8.37g, 0.11mol) to the ice-cooled system to obtain an orange solution; continue to stir for 30min, then add dropwise 2-bromopropionic acid (15.30g, 0.10mol) Into the system, and keep the temperature below 20°C, then dropwise add sodium hydroxide solution (4gNaOH, 0.1mol) with a mass fraction of 50%, and when the temperature of the system is at room temperature, add 15ml of distilled water; Add 25ml of distilled water to the system, keep the system in an ice bath, then add 15ml of concentrated hydrochloric acid solution dropwise until the system is acidic, and stir to keep the system at a low tempera...

Embodiment 2

[0038] A kind of preparation of the RAFT chain transfer agent containing terminal carboxyl group:

[0039] (1) 50% sodium hydroxide solution (4gNaOH, 0.1mol) is joined in the mixed solution of tert-butylmercaptan (9.02g, 0.1mol) and distilled water (15ml) under stirring state, then Add 5ml of acetone, and continue to stir for 30min; Add dropwise carbon disulfide (9.14g, 0.12mol) to the ice-cooled system to obtain an orange solution; Continue to stir for 30min, then add dropwise 2-bromopropionic acid (15.30g, 0.10mol) to system, and maintain the temperature below 20°C, then dropwise add sodium hydroxide solution (4gNaOH, 0.1mol) with a mass fraction of 50%, and when the temperature of the system is at room temperature, add 15ml of distilled water; Add 25ml of distilled water to keep the system under ice bath conditions, then add 15ml of concentrated hydrochloric acid solution dropwise until the system is acidic, and stir to keep the system at a low temperature; the yellow oil a...

Embodiment 3

[0044] A kind of preparation of the RAFT chain transfer agent containing terminal carboxyl group:

[0045] (1) 50% sodium hydroxide solution (4gNaOH, 0.1mol) is joined in the mixed solution of tert-butylmercaptan (9.02g, 0.1mol) and distilled water (15ml) under stirring state, then Add 5ml of acetone, continue to stir for 30min; then add dropwise carbon disulfide (8.37g, 0.11mol) to the ice-cooled system to obtain an orange solution; continue to stir for 30min, then add dropwise 2-bromopropionic acid (16.83g, 0.11mol) Into the system, and keep the temperature below 20°C, then dropwise add sodium hydroxide solution (4gNaOH, 0.1mol) with a mass fraction of 50%, and when the temperature of the system is at room temperature, add 15ml of distilled water; Add 25ml of distilled water to the system, keep the system in an ice bath, then add 15ml of concentrated hydrochloric acid solution dropwise until the system is acidic, and stir to keep the system at a low temperature; the yellow o...

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Abstract

The invention belongs to the field of organic synthesis and discloses a terminal alkynyl containing RAFT chain transfer agent and a preparation method and application thereof.The RAFT chain transfer agent has a structure shown in the description.The preparation method comprises the steps that tert-butyl mercaptan serves as a start raw material and reacts with carbon disulfide under the action of alkali to form trithiocarbonate; under the alkaline catalytic action, the obtained trithiocarbonate reacts with bromo propionate, and after acidification, terminal carboxylgroup containing RAFT chain transfer agent is obtained; the terminal carboxylgroup containing RAFT chain transfer agent is re-crystalized through n-hexane, and then under the action of EDC.HC1 and DMAP, the terminal carboxylgroup containing RAFT chain transfer agent and propargyl alcohol generate terminal alkynyl containing trithiocarbonate.The rough product is subjected to extraction and column chromatography, and then the product is obtained.The terminal alkynyl containing RAFT chain transfer agent can achieve RAFT polymerization and click reaction and prepare block polymer with specific structures and functions.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and particularly relates to a reversible addition-fragmentation chain transfer free radical polymerization chain transfer reagent (RAFT reagent) containing a terminal alkyne functional group and a preparation method and application thereof. Background technique [0002] Since the mechanism of RAFT living free radical polymerization was proposed, researchers began to invest in the research of RAFT reagents. The RAFT reagents that have been reported so far mainly include: (1) dithioester, (2) trithiocarbonate, (3) dithiocarbonate, (4) dithiocarbamic acid according to their different structures. ester. RAFT chain transfer agent (CTA) is the active center of RAF polymerization, its structure directly affects the polymerization process of RAFT polymerization and the molecular weight dispersion of polymers, and different types of free radical monomers are also suitable for RAFT chain transfer with dif...

Claims

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Application Information

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IPC IPC(8): C07C329/00C08F2/38
CPCC07C329/00C08F2/38
Inventor 廖兵黄利平庞浩黄健恒王璐雍奇文
Owner FOSHAN CENT FOR FUNCTIONAL POLYMER MATERIALS & FINE CHEM
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