Preparation method of novel crosslinking agent based on cyclodextrin derivative

A technology of cyclodextrin and cross-linking agent is applied in the field of preparation of new cross-linking agent, which can solve the problems of material toughness decrease, and achieve the effect of improving toughness and strength and increasing cross-linking reaction sites.

Inactive Publication Date: 2014-01-01
TIANJIN POLYTECHNIC UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Traditional cross-linking agents can connect linear molecules together to form a network structure. Although the strength is improved, as the degree of cross-linking continues to increase, the cross-linked material has the defect that the toughness decreases significantly.

Method used

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  • Preparation method of novel crosslinking agent based on cyclodextrin derivative
  • Preparation method of novel crosslinking agent based on cyclodextrin derivative

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Experimental program
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Effect test

Embodiment 1

[0023] Dissolve PEG-4000 (20g, 5mmol) in dichloromethane solution (100ml), add p-toluenesulfonyl chloride (3.81g, 20mmol) in triethylamine (28ml) solution, mix well, react at room temperature for 12h, and use 150ml of 1mol / L Extract with dilute hydrochloric acid, add excess sodium carbonate solution to the organic phase, stir well until no bubbles are generated, filter, and concentrate the filtrate with a rotary evaporator. (temperature about 40 degrees), remove dichloromethane, drip the concentrated filtrate into excess ether, get white precipitate, suction filter, then dissolve the suction filtrate in 10ml of dichloromethane, filter the insoluble matter, and The solution was dropped into excess diethyl ether to obtain a white precipitate, which was filtered by suction and dried in vacuum for 24 hours to obtain a white product. The final yield is above 90%.

Embodiment 2

[0025] Dissolve cyclodextrin (25.6g, 26.4mmol) in 200ml of water to form a solution, dissolve the p-tosylated polyethylene glycol (5.98g, 1.386mmol) prepared above in 136ml of distilled water, and dissolve p-toluenesulfonyl Add the aqueous solution of polyethylene glycol to the aqueous solution of cyclodextrin, ultrasonically treat for 30 minutes, stir overnight at room temperature, centrifuge the formed inclusion complex, and then put it in a vacuum drying oven to dry at 70°C to obtain the inclusion complex , the molar ratio of cyclodextrin to p-tosylated polyethylene glycol is 19:1. The final yield is above 92%.

Embodiment 3

[0027] 3,5-Dimethylphenol (10.32g, 84mmol) was dissolved in 144ml of DMF, and then slowly added dropwise into a round bottom flask of sodium hydride (4.0g). The solution turned brown and nitrogen was used as a protective gas during this process. Take the clathrate (13.94g) and dissolve it in 56ml of DMF, then add the above brown solution and stir for 12h. Divide the reaction solution into two beakers, add about 200ml of anhydrous methanol respectively, and filter to obtain a precipitate. Wash the precipitate with methanol twice, 20ml each time, dissolve the obtained precipitate in 40ml DMSO, then add 240ml of anhydrous methanol to obtain a precipitate, filter to obtain the precipitate, and wash with anhydrous methanol twice, each time 20ml. Then dissolve the precipitate in DMSO, add water to form a precipitate, filter the precipitate, and finally vacuum dry the precipitate in a vacuum drying oven at 110° C. overnight. The final yield was around 39%.

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Abstract

The invention relates to a novel crosslinking agent based on a cyclodextrin derivative and a preparation method thereof. The provided crosslinking agent making method has the characteristics of commercialized raw materials, convenient operation, green and environmental protection. At the same time, because of the movable properties of the cyclodextrin derivative, the cyclodextrin derivative based novel crosslinking agent is endowed with movable properties, thereby realizing movable crosslinking and increasing the cross-linking reaction sites to improve the cross-linking effect. The making method comprises: an inclusion process for mixing p-tosylation polyethylene glycol which has two ends subjected to p-tosylation with cyclodextrin molecules to obtain pseudopolyrotaxane; an end capping process for subjecting the pseudopolyrotaxane and a phenol derivative to an end capping reaction so as to obtain hydrogen removed 3, 5-dimethylphenol as an end capping agent to block two ends; and a process of reacting polyrotaxane with allyl glycidyl ether in the solvent dimethyl sulfoxide to obtain the novel crosslinking agent.

Description

technical field [0001] The invention relates to a preparation method of a novel cross-linking agent based on cyclodextrin derivatives, specifically, cyclodextrin and polyethylene glycol are used as basic materials, and a series of processes such as p-toluenesulfonylation, inclusion and end capping are carried out. process to prepare cyclodextrin derivatives. Then, using cyclodextrin derivatives as raw materials, a novel cross-linking agent based on cyclodextrin derivatives was prepared by reacting with allyl glycidyl ether (AGE) in the solvent dimethyl sulfoxide (DMSO). The raw materials of the invention are mostly commercial products, the operation is simple and the yield is high. Background technique [0002] With the continuous expansion of the application range of cross-linking agents in the field of polymer materials (rubber and thermosetting resins), higher requirements are put forward for cross-linking agents. Traditional crosslinking agents can connect linear molec...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F283/06C08F251/02C08B37/16C08G65/48C08G81/00
Inventor 林立刚王安栋董美美李巧玲张潮张龙辉刘春雨孙辉
Owner TIANJIN POLYTECHNIC UNIV
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