Trithiocarbonate compound containing epoxy group, preparation method and application thereof

A technology of trithiocarbonate and epoxy group is applied in the field of epoxy group-containing trithiocarbonate compound and its preparation, which can solve the problems of inability to prepare epoxy group-containing target substances and the like, and achieves the Good application prospects, easy adjustment, good reproducibility

Inactive Publication Date: 2012-10-24
ZHEJIANG SCI-TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] However, the terminals of the compound of formula ③ structure and the compound of formula ④ structure are both carboxyl groups, which will react with epoxy groups. Therefore, the target substance containing epoxy groups cannot be prepared by the technical scheme disclosed in the above-mentioned patent application.

Method used

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  • Trithiocarbonate compound containing epoxy group, preparation method and application thereof
  • Trithiocarbonate compound containing epoxy group, preparation method and application thereof
  • Trithiocarbonate compound containing epoxy group, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] (1) Preparation of 2-(n-butyltrithiocarbonate)propanecyanide

[0063] In general, the synthesis is divided into two steps, and the reaction scheme is as follows:

[0064]

[0065] C 4 h 9 SC(S)C(S)SC 4 h 9 +AIBN→2C 4 h 9 SC(S)SC(CH 3 ) 2 CN

[0066] Dissolve 3.85g of potassium tert-butoxide (BuOK) in 19.65g of tetrahydrofuran, and pour it into a 2000ml three-necked glass reaction kettle after completely dissolving. The solvent is 1000ml of n-heptane, and slowly add 3.09g of n-butyl at 5℃~10℃. Mercaptan, stirred mechanically for 30 minutes under nitrogen protection; then slowly added 2.63g carbon disulfide with a constant pressure funnel, the process continued for 20 minutes, continued to stir for 10 minutes after the addition, and then placed at 20°C~23°C for 4h, at 16°C~18°C Add 4.34 g of solid iodine particles in batches, the process lasts about 40 min, and react at room temperature 25°C for 15 h to generate a yellow-brown reaction product.

[0067] The y...

Embodiment 2

[0072] (1) Preparation of trithiocarbonate compounds containing epoxy groups.

[0073] Put the following reagents into a 500mL three-necked flask equipped with a reflux condenser, a nitrogen inlet, and a feed port: 25 grams of dioxane, 1.50 grams of the product of the formula 18 structure prepared in Example 1, and 0.06 grams of azodicyanovaleric acid. g and N,N-dimethylacrylamide 13 g. After passing high-purity (99.99%) nitrogen to the above device for 1 hour, immerse in a 70°C water bath and react for 15 hours to obtain an intermediate product; continue to add 25 grams of dioxane and 0.08 grams of azobiscyanovaleric acid to the three-necked flask , 5.6 grams of monomer B containing epoxy groups with the structure of formula 13 and 3.5 grams of n-butyl acrylate with the structure of formula 15, continue to react in a 70°C water bath for 1.5 hours, then cool down, stop the reaction, and pour the product into a 200mL ring In hexane, the precipitate was collected on a Buchner f...

Embodiment 3

[0076] (1) Preparation of trithiocarbonate compounds containing epoxy groups.

[0077] In a 500mL three-necked flask equipped with a reflux condenser, a nitrogen inlet, and a feed port, the following reagents were dropped: 20 grams of dioxane, 0.54 grams of the product of the formula 18 structure prepared in Example 1, and 0.03 grams of azodicyanovaleric acid. g and N,N-dimethylacrylamide 7.0 g. After passing high-purity (99.99%) nitrogen to the above device for 1 hour, immerse in a 70°C water bath and react for 15 hours to obtain an intermediate product; continue to add 10 grams of dioxane and 0.08 grams of azodicyanovaleric acid to the three-necked flask 1.026 grams of epoxy-group-containing monomers of formula 12 and 0.576 grams of n-butyl acrylate of formula 15 were reacted in a water bath at 70°C for 2 hours, then the temperature was lowered to stop the reaction, and the product was poured into 200 mL of cyclohexane The precipitate was collected with a Buchner funnel. T...

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Abstract

The invention discloses a trithiocarbonate compound containing an epoxy group, as shown in formula I. The trithiocarbonate compound containing the epoxy group has an amphiphilic structure of both hydrophilicity and lipophilicity, wherein the epoxy group is between the hydrophilic chain segment and the oleophylic chain segment. The invention also discloses a preparation method for the trithiocarbonate compound containing the epoxy group. The preparation method is simple and practicable. A first step copolymerization is carried out between a compound having a structure of formula II and a water-soluble monomer D in the presence of a radical initiator, and a second step copolymerization is carried out with an epoxy group-containing monomer B and a hydrophobic monomer A, so the compound having the structure of formula I is obtained. The preparation method has the characteristics of simpleness and practicality, mild reaction condition, strong operationality, good reappearance, and the like. The invention further discloses an application of the trithiocarbonate compound containing the epoxy group in preparing polymer microspheres, enabling the epoxy groups to be enriched on surfaces of the polymer microspheres.

Description

technical field [0001] The invention relates to the field of trithiocarbonate compounds, in particular to a trithiocarbonate compound containing an epoxy group and a preparation method and application thereof. Background technique [0002] Surface cross-linked latex particles (SCL, Shell cross-linked latexes) can be used as micro-nano containers for wrapping drugs, spices, pesticides, etc., and are widely used in the fields of medicine, chemical industry, and biology. Synthesizing latex particles with reactive functional groups on the surface, and the subsequent reaction of the functional groups is one of the methods for efficiently synthesizing the above-mentioned SCL. [0003] Among the many functional groups, the epoxy group has high reactivity, and can undergo nucleophilic addition reaction with basic compounds containing active hydrogen, such as amine groups, and can react with acidic groups containing active hydrogen, such as carboxyl groups. , alcoholic hydroxyl grou...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F293/00C08F220/54C08F220/56C08F220/28C08F2/24C08F112/08C08F120/18
Inventor 杨雷孙鹏杨海周利展戚栋明
Owner ZHEJIANG SCI-TECH UNIV
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