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Preparation method of high-performance carboxyl-terminated low-molecular-weight fluorine-containing polymer

A low molecular weight, polymer technology, applied in the direction of additive processing, etc., can solve the problems of product thermal, chemical stability and functionalization, and achieve the effect of mild conditions

Active Publication Date: 2021-01-29
SHENYANG INSTITUTE OF CHEMICAL TECHNOLOGY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] With the deepening of research, it is found that although the oxidative degradation method can be used to prepare carboxyl-terminated low-molecular-weight fluorine-containing polymers with controllable molecular weight and functional group content, the chain contains unsaturated double bonds, which will affect the thermal and chemical stability of the final product. and subsequent functionalization will have some impact

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  • Preparation method of high-performance carboxyl-terminated low-molecular-weight fluorine-containing polymer

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] 10g of carboxyl-terminated low-molecular-weight fluoropolymer (carboxyl-terminated vinylidene fluoride-hexafluoropropylene binary copolymer, number average molecular weight 3500, double bond content of 1.47mol% or 0.17mmol / g, thermal decomposition temperature of 208°C, fluorine Content 64%), dissolved in 100ml tetrahydrofuran, placed in a 500ml single-necked flask. Add the fluorinating reagent N-fluoro-N'-(chloromethyl)triethylenediamine bis(tetrafluoroborate) (60.22mg, 0.17mmol) and the nucleophile silver fluoride (21.57mg, 0.17mmol) in sequence After 4 hours of reaction, the hydrogenation reagent lithium aluminum hydride (6.45mg, 0.17mmol) and the electrophile N-bromosuccinimide (30.26mg, 0.17mmol) were added, and the temperature was raised to 25°C for 4 hours of reaction. After the reaction, the organic phase was left to stand and collected, and the solvent was removed, and the product was vacuum-dried at 50-70° C. for 24 hours.

[0026] The product was subjected to...

Embodiment 2

[0029] Take 10g of carboxyl-terminated low-molecular-weight fluorine-containing polymer (carboxyl-terminated vinylidene fluoride-hexafluoropropylene binary copolymer, number average molecular weight 3200, double bond content of 1.15mol% or 0.12mmol / g, thermal decomposition temperature of 230°C, fluorine Content 63.8%), dissolved in 110ml acetone, placed in a 500ml single-necked flask. 1-Fluoro-4-methyl-1,4-diazabicyclo[2.2.2]octane tetrafluoroborate (57.57mg, 0.18mmol), potassium fluoride (10.46mg, 0.18mmol), After reacting for 4 hours, sodium borohydride (6.81mg, 0.18mmol) and N-fluorobenzenesulfonimide (56.76mg, 0.18mmol) were added, the temperature was raised to 30°C, and the reaction was carried out for 5 hours. After the reaction, the organic phase was left to stand and collected, and the solvent was removed, and the product was vacuum-dried at 50-70° C. for 24 hours.

[0030] product 19 According to F-NMR, the characteristic peak intensity corresponding to the double b...

Embodiment 3

[0033] 10g of carboxyl-terminated low-molecular-weight fluoropolymer (carboxyl-terminated vinylidene fluoride-hexafluoropropylene binary copolymer, number average molecular weight 2600, double bond content of 0.95mol% or 0.10mmol / g, thermal decomposition temperature 232°C, fluorine Content 62.7%), dissolved in 120ml of acetonitrile, placed in a 500ml single-necked flask. Add triethylamine hydrofluoride (32.24mg, 0.20mmol) and diethylaminosulfur trifluoride (24.18mg, 0.15mmol) successively. After 4 hours of reaction, add potassium borohydride (10.79mg, 0.20mmol), N-iodosuccinimide (33.75mg, 0.15mmol) was heated up to 35°C and reacted for 5 hours. After the reaction, the organic phase was left to stand and collected, and the solvent was removed, and the product was vacuum-dried at 50-70° C. for 24 hours.

[0034] product 19 According to F-NMR, the characteristic peak intensity corresponding to the double bond structure is obviously weakened, the calculated double bond content ...

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Abstract

The invention discloses a preparation method of a high-performance carboxyl-terminated low-molecular-weight fluorine-containing polymer, belonging to a polymer preparation method. According to the invention, a carboxyl-terminated low-molecular-weight fluorine-containing polymer containing double bonds in a chain and prepared by an oxidative degradation method is used as a raw material, a fluorinated addition reaction system and method for the fluorine-containing polymer are created, N-fluoro-N'-(chloromethyl)triethylenediamine bis(tetrafluoroborate) or a hydrogen fluoride complex and the likeare used as fluorinating reagents, lithium aluminum hydride or borohydride is used as a hydrogenation reagent, silver fluoride and the like are used as nucleophilic reagents, and N-bromosuccinimide and the like are used as electrophilic reagents, so a fluorine content is increased while saturation of double bonds in a chain is realized, and the thermal stability of the polymer is greatly improved.The method is simple in process, mild in reaction conditions and high in efficiency; a saturation rate reaches 80% or above, the fluorine content of the produced polymer is higher than 66%, and the polymer can serve as a fluorine-containing precursor of a functional polymer and an additive manufacturing (3D printing) raw material and can also be applied as a high-performance adhesive, a joint mixture, a coating, a processing compounding agent and the like.

Description

technical field [0001] The invention relates to a method for preparing a polymer, in particular to a method for preparing a high-performance carboxyl-terminated low-molecular-weight fluorine-containing polymer. Background technique [0002] Functionalized low molecular weight fluoropolymer not only has a main chain structure and monomer composition similar to solid fluororubber, but also has excellent thermal stability, oil resistance and chemical resistance, and has incomparable fluidity and plasticity of solid fluororubber , is easier to process, form and cure, and is an indispensable and irreplaceable important high-performance material in the transportation, defense and aviation industries. [0003] At present, the production and R&D technology of functionalized low molecular weight fluoropolymers are mainly concentrated in DuPont, 3M, Russian Lebedev Synthetic Rubber Research Institute and Daikin Corporation of Japan. The research on preparation, functionalization and ...

Claims

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Application Information

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IPC IPC(8): C08F8/20C08F214/22B33Y70/00
CPCC08F8/20B33Y70/00C08F214/22
Inventor 李东翰段佳玉康海澜方庆红杨凤李龙韩文驰
Owner SHENYANG INSTITUTE OF CHEMICAL TECHNOLOGY
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