Preparation method of polymerizable non-ionic fluorine-containing short chain surfactant

A surfactant, non-ionic technology, applied in the field of preparation of polymerizable non-ionic fluorine-containing short-chain surfactants, can solve the problem of reducing surface/interface energy, limiting the application of polymerizable emulsifiers, reducing surface activity, etc. problems, achieve high surface activity and polymerizability, easy access, and stable performance

Active Publication Date: 2019-05-17
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although cross-linking is beneficial to the improvement of the performance of UV-curable resins, it is very unfavorable for conventional emulsion polymerization, which will lead to adverse consequences such as gels.
Therefore, although the technical route of this invention contributes to the application of the surfactant described in the patent in the field of UV-curable resins, it limits its application as a polymerizable emulsifier in conventional emulsion polymerization
In addition, other by-products of the inventive route, such as the superhydrophobic by-products of three fluorocarbon chains and the complete hydrophilic by-products of three polyethylene glycol chains, will also lead to a reduction in the surface activity of the resulting target product, which cannot obtain optimal Surface / interface energy reduction effects
At the same time, the surfactant uses highly toxic dibutyltin dilaurate as a catalyst in the synthesis process, which poses certain safety risks to organisms and the environment, especially when it is used in the production of products that are in close contact with the human body. Strict restrictions

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Example 1: Place the activated 3A molecular sieves in short-chain fluoroalcohols and hydroxyalkyl acrylates respectively, seal them overnight, and remove moisture; at 100~120°C, under the conditions of a vacuum of 0.009MPa, polyethylene glycol Distill under reduced pressure to remove water; dry the three-necked bottle, agitator, and feeding tube at 100-120°C for 2-4 hours, take it out and put it in a desiccator to cool; Add 2.22 g of isophorone diisocyanate, 2.64 g of 2-perfluorobutyl ethyl alcohol and 10 μL of organic bismuth catalyst, heat to 55 ° C in a water bath with stirring, and react for 6 hours; raise the temperature to 75 ° C, add 8 g of Polyethylene glycol, react for 8 hours; then lower the temperature to 65°C, add 2.22g of isophorone diisocyanate, and react for 6 hours; finally lower the temperature to 55°C, add 1.16g of hydroxyethyl acrylate, and continue to react for 8 hours. A polymerizable nonionic fluorine-containing short-chain surfactant is obtained. ...

Embodiment 2

[0033] Example 2: Place the activated 3A molecular sieves in short-chain fluoroalcohols and hydroxyalkyl acrylates respectively, seal them overnight, and remove moisture; at 100~120°C, under the conditions of a vacuum of 0.009MPa, the polyethylene glycol Distill under reduced pressure to remove water; dry the three-necked bottle, agitator, and feeding tube at 100-120°C for 2-4 hours, take it out and put it in a desiccator to cool; Add 2.22 g of isophorone diisocyanate, 1.5 g of pentafluoropropanol and 10 μL of organic bismuth catalyst, heat to 55 ° C in a water bath with stirring, and react for 6 hours; raise the temperature to 75 ° C, add 6 g of polyethylene glycol with a number average molecular weight of 600 , reacted for 8 hours; then lowered the temperature to 65°C, added 2.22g of isophorone diisocyanate, and reacted for 6 hours; finally lowered the temperature to 55°C, added 1.16g of hydroxyethyl acrylate, and continued to react for 8 hours to obtain polymerizable non- I...

Embodiment 3

[0034] Example 3: Place the activated 3A molecular sieves in short-chain fluoroalcohols and hydroxyalkyl acrylates respectively, seal them overnight, and remove moisture; at 100~120°C, under the condition of a vacuum of 0.009MPa, the polyethylene glycol Distill under reduced pressure to remove water; dry the three-necked bottle, agitator, and feeding tube at 100-120°C for 2-4 hours, take it out and put it in a desiccator to cool; Add 2.22g of isophorone diisocyanate, 1.68g of 1,1,1,3,3,3-hexafluoro-2-propanol and 10 μL of organic bismuth catalyst, stir and heat to 55°C in a water bath, and react for 6 hours; 75°C, add 6g of polyethylene glycol with a number average molecular weight of 600, and react for 8 hours; then cool down to 65°C, add 2.22g of isophorone diisocyanate, and react for 6 hours; finally cool down to 55°C, add 1.3g of formazan hydroxyethyl acrylate, and continue to react for 8 hours to obtain a polymerizable nonionic fluorine-containing short-chain surfactant. ...

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PUM

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Abstract

The invention discloses a preparation method of a polymerizable non-ionic fluorine-containing short chain surfactant. The surfactant is obtained in the modes that firstly, short-chain fluorol and isophorone diisocyanate react in the same mole ratio to obtain an intermediate I with a monoisocyanate group, then the intermediate I is coupled with polyethylene glycol in the same mole ratio to obtain an intermediate II with monohydroxyl, then the intermediate II is coupled with isophorone diisocyanate in the same mole ratio to obtain an intermediate III with one end provided with an isocyanate group, and finally the intermediate III and hydroxyalkyl acrylate generate a coupling reaction in the same mole ratio. The preparation method has the advantages that the surfactant has polymerization andhigh surfactivity, meanwhile, a short fluorine-carbon chain in the surfactant enables the surfactant to have the low bioaccumulation, a polyurethane structure enables the surfactant to have good later-period environmental degradation, organic solvents are not used in the synthesis process, and thus environmental friendliness is achieved; and the surfactant can be used as a waterproof and oil-proofassistant, a coating leveling agent and the like, and has wide application prospects.

Description

technical field [0001] The invention relates to a preparation method of a surfactant, in particular to a preparation method of a polymerizable nonionic fluorine-containing short-chain surfactant. Background technique [0002] As a special surfactant, fluorine-containing surfactant has the characteristics of "three highs" and "two phobias", that is, high surface activity, high heat resistance and high chemical stability, and the fluorocarbon chain is both hydrophobic and repellent. Oil. In view of its excellent performance, fluorosurfactants are widely used in fire extinguishing, paint leveling, fabric or leather finishing, etc. [0003] Traditional fluorosurfactants are mainly represented by perfluorooctanesulfonic acid (PFOS) and perfluorooctanoic acid (PFOA), but related studies have shown that these long fluorocarbon chain (CnFn+1,n≥7) compounds have high toxicity , environmental persistence and bioaccumulation. Therefore, the United Nations Environment Program (EPA) d...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G18/75C08G18/67C08G18/48C08G18/28B01F17/00C09K23/00
Inventor 金勇周荣金泓宇龙晨辉
Owner SICHUAN UNIV
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