Nitrogen-containing heterocyclic fluorocarbon surfactant synthesized by adopting photoreaction-click reaction method and preparation of water-phase micelle of nitrogen-containing heterocyclic fluorocarbon surfactant

A click reaction and fluorocarbon surface technology is applied in the field of organic photochemistry to achieve the effects of simple and easy synthesis method, simple preparation, and simple purification operation.

Active Publication Date: 2021-10-22
山东盛安贝新材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the photochemical synthesis of functional fluorocarbon surfactants has not been reported

Method used

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  • Nitrogen-containing heterocyclic fluorocarbon surfactant synthesized by adopting photoreaction-click reaction method and preparation of water-phase micelle of nitrogen-containing heterocyclic fluorocarbon surfactant
  • Nitrogen-containing heterocyclic fluorocarbon surfactant synthesized by adopting photoreaction-click reaction method and preparation of water-phase micelle of nitrogen-containing heterocyclic fluorocarbon surfactant
  • Nitrogen-containing heterocyclic fluorocarbon surfactant synthesized by adopting photoreaction-click reaction method and preparation of water-phase micelle of nitrogen-containing heterocyclic fluorocarbon surfactant

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028]The first step is to invest in N- (3-lamnopropyl) -N- (for methoxy sulfonyl) methacrylamide (676 mg, 0.002 mol) and 1-iodide perfluoroctane. (1416 mg, 0.0013 mol), an optical catalyst IR of a molar ratio of N- (3-azide-propylene) -N- (for methoxy sulfonyl) methacrylamide is added to a photocatalytic IR of 3% (38 mg, 0.00006 mol) (PPY) 3 And the molar ratio of N- (3-azide-propylene) -N- (for methoxysulfonyl) methacrylamide is 2 (830 mg, 0.002 mol) of potassium phosphate K 3 PO 4 , 15 ml of the organic solvent dioxane (Dioxane) was added as a solvent, and an ultraviolet-visible light was used as a photolraction container and stirred for 24 h, and a photochemical molecule was closed, and the reaction product was subjected to silica gel column chromatography isolation purification (eluent ethyl acetate : Petroleum ether volume ratio V: v = 5: 1) Butketate (860 mg, 62%). The ultraviolet-visible light source is Bluewave15W / CM 2 LED Prime Uva Spot Curing System, Penang, Malaysi...

Embodiment 2

[0035] The first step is to invest N- (3-laminated nitrogen-based) -N- (methoxy sulfonyl) methacrylamide (338 mg, 0.001 mol) and 1-iodide perfluoroctane. (708 mg, 0.0013 mol), an optical catalyst IR of a molar ratio of N- (3-azide-propylene) -N- (for methoxy sulfonyl) methacrylamide is added. (PPY) 3 And the molar ratio of N- (3-azide-propylene) -N- (for methoxyulfonyl) methacrylamide is 2 (415 mg, 0.002 mol) of potassium phosphate K 3 PO 4 The 7 ml of the organic solvent dioxane (Dioxane) was added as a solvent, and the ultraviolet-visible light was used as a photoreactive reaction vessel and stirred for 24 h, and the inner closed loop reaction in photochemical molecules was carried out, and the reaction product was subjected to silica gel column chromatography isolation purification (eluent ethyl acetate : Petroleum ether volume ratio V: v = 5: 1) Butketate (402 mg, 58%). The ultraviolet-visible light source is Bluewave15W / CM 2 LED Prime Uva Spot Curing System, Penang, Malay...

Embodiment 3

[0042] The first step is to invest in N- (3-lamnopropyl) -N- (for methoxy sulfonyl) methacrylamide (676 mg, 0.002 mol) and 1-iodide perfluoroctane. (1416 mg, 0.0013 mol), an optical catalyst IR of a molar ratio of N- (3-azide-propylene) -N- (for methoxy sulfonyl) methacrylamide is added to a photocatalytic IR of 3% (38 mg, 0.00006 mol) (PPY) 3 And the molar ratio of N- (3-azide-propylene) -N- (for methoxysulfonyl) methacrylamide is 2 (830 mg, 0.002 mol) of potassium phosphate K 3 PO 4 , 15 ml of the organic solvent dioxane (Dioxane) was added as a solvent, and an ultraviolet-visible light was used as a photolraction container and stirred for 24 h, and a photochemical molecule was closed, and the reaction product was subjected to silica gel column chromatography isolation purification (eluent ethyl acetate : Petroleum ether volume ratio V: v = 5: 1) Butketate (943 mg, 68%). The ultraviolet-visible light source is Bluewave15W / CM 2 LED Prime Uva Spot Curing System, Penang, Malays...

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Abstract

The invention belongs to the crossing field of organic photochemistry, organic fluorine chemistry and medicinal surfactant chemistry, and particularly relates to a nitrogen-containing heterocyclic fluorocarbon surfactant synthesized by adopting a photoreaction-click reaction method and preparation of a water-phase micelle of the nitrogen-containing heterocyclic fluorocarbon surfactant. An intermediate 1-N-(3-azidopropyl)-3-methyl-3-perfluorooctyl-5-methoxyl-indolone is synthesized by adopting a photoreaction, photochemical intramolecular ring-closure reaction is carried out by using ultraviolet-visible light irradiation, and under the catalysis of copper sulfate/sodium ascorbate, the intermediate and monopropynyl-monomethyl-polyethylene glycol are subjected to a click reaction, and the nitrogen heterocyclic ring fluorocarbon surfactant is prepared. The green synthesis method is simple and easy to implement, low-toxicity, efficient and commercialized green chemical reagents are used in the synthesis process, and the synthesis method is atom-economical. The preparation method passes a small-amount synthesis test in a laboratory and is successful. Then, water-phase micelles of the nitrogen-containing heterocyclic fluorocarbon surfactant are prepared and are characterized.

Description

Technical field [0001] The present invention belongs to organic photochemical, organoic fluorochemistry, and pharmaceutically acceptable chemical crossains, and more particularly Preparation. Background technique [0002] The present invention is intended to illustrate the contents of the present invention, and should not be understood that the applicant is clearly considered or estimated by the applicant to express the application for the present invention, the applicant is approved. The prior art of the day. [0003] The fluorocarbon surfactant is replaced by a fluorine atom, i.e., a fluorocarbon chain, is replaced by a fluorine atom. Strong bonding capacity of fluorine atom and carbon atom (4.86 × 10 5 J / mol) is given to the fluorocarbon surfactant with a variety of special properties, the shield of the fluorine atoms increases the stability of the fluorocarbon type surfactant to make it chemically resistant to chemical properties and thermal stability. The surface tension o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/06B01F17/42B01F17/32B01J13/00C09K23/32C09K23/42
CPCC07D403/06B01J13/0065Y02P20/584
Inventor 姜珍华盛瑞隆赵嘉邵昌尧司洪福许传昊周法政许延想
Owner 山东盛安贝新材料有限公司
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