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Preparation method and application of trithiocarbonic acid ester compound containing isocyanate group

A technology of trithiocarbonate and isocyanate group, which is applied in the field of preparation of trithiocarbonate compounds, can solve the problems of inability to prepare the target compound containing isocyanate group, etc., and achieves strong operability, easy adjustment of sequence structure, and ease of use. The effect of adjustment

Inactive Publication Date: 2014-04-23
ZHEJIANG SCI-TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] But the end of the compound of formula ③ structure and the compound of formula ④ structure are both carboxyl groups, which will react with isocyanate groups. Therefore, it is impossible to prepare the target substance containing isocyanate groups through the technical scheme disclosed in the above patent application.

Method used

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  • Preparation method and application of trithiocarbonic acid ester compound containing isocyanate group
  • Preparation method and application of trithiocarbonic acid ester compound containing isocyanate group
  • Preparation method and application of trithiocarbonic acid ester compound containing isocyanate group

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] (1) Preparation of 2-(n-butyltrithiocarbonate)propanecyanide

[0068] In general, the synthesis is divided into two steps, and the reaction scheme is as follows:

[0069]

[0070] C 4 h 9 SC(S)C(S)SC 4 h 9 +AIBN→2C 4 h 9 SC(S)SC(CH 3 ) 2 CN

[0071] 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.

[0072] The y...

Embodiment 2

[0077] (1) Preparation of trithiocarbonate compounds containing isocyanate groups

[0078] Put the following reagents into a 250mL three-necked flask equipped with a reflux condenser, a nitrogen inlet, and a feed port: 20 grams of dioxane, 0.4617 grams of the product of the formula 16 structure prepared in Example 1, and 0.0183 grams of azodicyanovaleric acid and N,N-dimethylacrylamide 9.0372 grams. After the above device was passed through high-purity (99.99%) nitrogen for 1 hour, it was immersed in a 70°C water bath, and after 18 hours of reaction, an intermediate product was obtained; continue to add 15 grams of dioxane and 0.027 g of azodicyanovaleric acid to the three-necked flask. gram, 2.5 grams of isocyanate group-containing monomers with the structure of formula 10 and 5 grams of styrene (that is, the structure of formula 14), continue to react in a 75 ° C water bath for 12 hours, then cool down, stop the reaction, and obtain the product. The product was poured into ...

Embodiment 3

[0081] (1) Preparation of trithiocarbonate compounds containing isocyanate groups

[0082] The following reagents were dropped into a 250mL three-necked flask equipped with a reflux condenser, a nitrogen inlet, and a feed port: 18 grams of dioxane, 0.7067 grams of the product of the formula 16 structure prepared in Example 1, 0.0328 grams of azobisisobutyronitrile and N,N-Dimethacrylamide 9.0372 g. After passing high-purity (99.99%) nitrogen to the above device for 0.5 hours, immerse in a 70°C water bath, and react for 18 hours to obtain an intermediate product; continue to add 6 grams of dioxane and 0.0164 grams of azobisisobutyronitrile into the three-necked flask 1.39 grams of isocyanate group-containing monomers with the structure of formula 12 and 5.8 grams of n-butyl acrylate (that is, the structure of formula 13) were reacted in a 75°C water bath for 12 hours, then the temperature was lowered, and the reaction was stopped to obtain the product. The product was poured i...

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Abstract

The invention discloses a trithiocarbonic acid ester compound containing isocyanate group, and the compound has a structure of formula I. The invention also discloses a preparation method of the trithiocarbonic acid ester compound containing an isocyanate group. The method comprises a first step of copolymerization reaction by a compound having a structure of formula II and a water-soluble monomer which forms a chain unit D under the effect of a radical initiator, and a second step of copolymerization reaction of the obtained product with a monomer B having an isocyanate group and a hydrophobic monomer A, so the compound having the structure of formula I is obtained. The preparation method has the characteristics of being simple, good operationality and reappearance, etc. The invention further discloses an application of the trithiocarbonic acid ester compound containing isocyanate group in preparing polymer microspheres, which enables the isocyanate groups to gather on the surfaces of the polymer microspheres.

Description

technical field [0001] The invention relates to the field of preparation of trithiocarbonate compounds, in particular to a trithiocarbonate compound containing isocyanate groups and its preparation method and application. Background technique [0002] Due to the low content of volatile organic compounds (VOC) in water-based coatings, it is safe and convenient to use, and it is easy to use and is not limited by the application. Therefore, in the past 30 years, the amount has increased year by year, and it has become the main product of coatings. However, so far, there are still many problems to be solved in waterborne coating systems. For example: latex particles with a hard core-soft shell structure can improve the film-forming properties of latex to a certain extent, but the strength of the coating film is not high, and it needs to be enhanced by the cross-linking reaction between the particles in the film-forming process. [0003] The isocyanate group is a functional grou...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F293/00C08F220/54C08F220/56C08F220/28C08F212/14C08F220/36C08F212/08C08F220/18C08F226/02C08F2/24B01J13/14
Inventor 杨雷孙鹏周利展杨海戚栋明
Owner ZHEJIANG SCI-TECH UNIV