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Cardanol-based trithiocarbonate and its synthesis method and application

A technology of thiol compounds and carboxyl groups, applied in the field of chemistry, can solve the problems of inability to use coatings, inks, adhesives, polymers, poor water resistance, poor scratch resistance, etc., and achieves a wide range of applicable monomers and broad application prospects. , the effect of a simple synthesis method

Inactive Publication Date: 2014-10-29
JIANGXI SCI & TECH NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Traditional emulsion polymerization often uses small-molecule emulsifiers, and these small-molecule emulsifiers will eventually enter the polymer product, which will adversely affect the product. For example, the small-molecule emulsifier will migrate to the surface, making the polymer water-resistant Deterioration, and affect the optical, electrical and surface properties of the product (M.Save,Y.Guillaneuf andR.G.Gilbert.Aust.J.Chem.2006,59,693-711.)
[0005] The disadvantages of linear polymers are low mechanical strength, poor scratch resistance, weak chemical corrosion resistance, and easy aging, so people often make cross-linked polymers for use
However, if it is directly made into a cross-linked polymer, it cannot be used in coatings, inks, and adhesives because it is a thermosetting resin that only swells and does not dissolve.

Method used

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  • Cardanol-based trithiocarbonate and its synthesis method and application
  • Cardanol-based trithiocarbonate and its synthesis method and application
  • Cardanol-based trithiocarbonate and its synthesis method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] The preparation of embodiment 1 4-bromobutyl cardanol ether (IVa)

[0027] The target compound was prepared from cardanol, 1,4-dibromobutane and alkali.

[0028] 1,4-Dibromobutane (2.70g, 12.5mmol), sodium bicarbonate (8.4g, 100mmol) and tetrahydrofuran (5mL) were added to the reaction flask, then cardanol (1.21g, 4mmol) was slowly added dropwise into the reaction mixture. After adding the material, react at room temperature for 24h. Add 100mL of water to the system, separate the layers, add anhydrous sodium sulfate to the organic phase to dry, and finally evaporate the solvent to obtain a yellow oil. The crude product was purified by silica gel column (eluent: ether / dichloromethane=1 / 1, volume ratio) to obtain pure product (1.25g, 71%).

[0029] 1 H NMR (400MHz, CDCl 3 ):δ7.24-7.15(m,1H),6.83-6.71(m,3H),5.89-5.82(m,0.3H),5.49-5.34(m,3H),5.12-5.00(m,0.6H) ,4.02(t,2H,J=6.0Hz),3.54-3.44(m,5H),2.88-2.81(m,2H),2.63(m,2H),2.16-2.00(m,8H),1.99-1.92 (2H),1.66-1.57(m,2H)...

Embodiment 2

[0031] Example 2 Preparation of Cardanol-based Reversible Addition-Fragmentation Chain Transfer Reagent (Ia) Using Compound IVa Synthesized in Example 1

[0032] The target compound was prepared from compound IVa, carbon disulfide, 3-mercaptopropionic acid and base.

[0033] Sodium carbonate (0.74g, 7mmol), 3-mercaptopropionic acid (0.75g, 7mmol), and acetone (30mL) were added to the reaction flask, the mixture was stirred at reflux temperature for 30min, cooled, 2mL of carbon disulfide was added, and then the mixture was Stir at room temperature for 1 h. Compound IVa (3.0g, 7mmol) was slowly added into the reaction system, and then reacted at room temperature for 2h. After the reaction was completed, it was concentrated under reduced pressure to obtain a yellow oil. The oil was dissolved in dichloromethane, washed 5 times with water, dried over anhydrous sodium sulfate, filtered and concentrated to obtain a crude product. The crude product was purified by silica gel column...

Embodiment 3

[0037] Example 3 Reversible addition-fragmentation chain transfer polymerization of methyl methacrylate (MMA) using the cardanol-based reversible addition-fragmentation chain transfer reagent (Ia) prepared in Example 2

[0038] Methyl methacrylate (3.00 g, 30 mmol), cardanol group reversible addition-fragmentation chain transfer reagent (Ia) (0.54 g, 1.0 mmol), potassium persulfate (0.13 g, 0.57 mmol) were dissolved in acetonitrile (25 mL )middle. Under ice-water cooling, the reaction flask was first evacuated, then filled with nitrogen, and repeated three times. The reaction solution was heated to 70° C. and kept constant, and then sodium sulfite (0.15 g, 1.25 mmol) was added for reaction. After 4 hours, the heating was stopped, and water or lower alcohols such as methanol and ethanol were added to the reaction flask, and a precipitate was generated, and the solid was filtered out, and the solid was dried in a vacuum oven at 65° C. for 24 h. Monomer conversion was determine...

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Abstract

The invention relates to the field of chemical synthesis, and discloses cardanol trithiocarbonate and a preparation method thereof, wherein the preparation method comprises the following steps: cardanol is etherified with dihalide, and then reacts with carbon disulfide and a mercaptan compound to obtain a final product. The cardanol trithiocarbonate can be used as reversible addition-fragmentation chain transfer reagent, and can be used for preparing light-cured resins.

Description

technical field [0001] The invention relates to the field of chemistry, in particular to the synthesis of a cardanol-based reversible addition-fragmentation chain transfer (RAFT) reagent and its application in prepared resin. Background technique [0002] In recent years, with the increasingly scarce fossil resources and energy, people pay more and more attention to the research of other alternative resources. Among them, renewable resources from animals and plants have become one of the research hotspots. Cashew nut shell liquid (CNSL) is a liquid component extracted from the cashew nut shell. It is a by-product of cashew nut processing, of which cardanol content accounts for about 90%. If these by-products are not used but discharged into the environment, it will pollute the environment. At present, the annual output of cashew nut shell oil in the world is about 500,000 tons, which is a rich and cheap renewable resource. From the current point of view, the use of cardan...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C329/00C08F2/38
Inventor 程传杰涂远明王晓季肖强
Owner JIANGXI SCI & TECH NORMAL UNIV
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