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Organic fluorine-silicon surface treatment agent and preparation method thereof

A silicon surface and treatment agent technology, which is applied in the field of organofluorine silicon surface treatment agent and its preparation, can solve the problems of poor stability, low conversion rate, poor surface activity, etc., and achieve excellent high and low temperature resistance, oil resistance and solvent resistance. Effect

Active Publication Date: 2016-02-17
ZHEJIANG HAPPY CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are two main problems in the synthesis of fluorine-containing surfactants using hexafluoropropylene trimer as a fluorine-containing precursor material: one is that the perfluoroalkyl chain of hexafluoropropylene trimer is shorter than that of PFOS and PFOA, and it has branched chain structure, so the surface activity of hexafluoropropylene trimer derivatives is relatively poor, and has not been widely used; the second is that hexafluoropropylene trimer is derivatized as a fluorine-containing precursor material, and the reaction type is mainly vinyl fluoride Nucleophilic substitution, generally the compounds derived by alkyl nucleophiles have poor stability, and it is necessary to select a chemically stable linking chain structure to improve its stability
The introduction of connecting chains makes the synthesis route more complex, while the conversion rate decreases and the production cost rises, which limits the widespread use of hexafluoropropylene trimer surfactants

Method used

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  • Organic fluorine-silicon surface treatment agent and preparation method thereof
  • Organic fluorine-silicon surface treatment agent and preparation method thereof
  • Organic fluorine-silicon surface treatment agent and preparation method thereof

Examples

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Effect test

Embodiment 1

[0037] An organosilicon-fluorine surface treatment agent, which uses hexafluoropropylene trimer as a modifier, ethylene glycol dimethyl ether as a solvent, and triethylamine as a catalyst, through aminopropyltriethoxysilane -NH 2 The group undergoes a nucleophilic substitution reaction with the double-bond fluorine atom of the hexafluoropropylene trimer to synthesize a fluorosilicone compound as shown in the structural formula (VI).

[0038] (VI):

[0039] Concrete reaction steps are as follows:

[0040] Add 90ml of ethylene glycol dimethyl ether, 6.9g of triethylamine, and 30.6g of hexafluoropropylene trimer into the reaction bottle, stir evenly, raise the temperature to 30°C and add 17g of aminopropyltriethoxysilane dropwise, and dropwise The time is 50min, the dropwise addition is completed, and the temperature is raised to 60°C for 3h; after the reaction is completed, distill under reduced pressure at 0.1Mpa and 90°C for 2h to remove the solvent glycol dimethyl ether, ca...

Embodiment 2

[0042] An organosilicon fluorine surface treatment agent, which uses hexafluoropropylene trimer as a modifier, ethylene glycol dimethyl ether as a solvent, and triethylamine as a catalyst, through aminoethylaminopropylmethyl dimethyl -NH of oxysilane 2 The group undergoes a nucleophilic substitution reaction with the double-bond fluorine atom of the hexafluoropropylene trimer to synthesize a fluorosilicone compound as shown in structural formula (VII).

[0043] (Ⅶ):

[0044] Concrete reaction steps are as follows:

[0045] Add 100ml of ethylene glycol dimethyl ether, 6.9g of triethylamine, and 30.6g of hexafluoropropylene trimer to the reaction flask in sequence, stir evenly, raise the temperature to 30°C, and add aminoethylaminopropylmethyldimethoxy 14g of silane, the dropping time is controlled to be 50min. After the dropping is completed, the temperature is raised to 50°C for 3h; after the reaction is completed, vacuum distillation is carried out at 0.1Mpa and 90°C for ...

Embodiment 3

[0047] An organosilicon fluorine surface treatment agent, is that hexafluoropropylene trimer is used as a modifier, ethylene glycol dimethyl ether is used as a solvent, and triethylamine is used as a catalyst, and the general structural formula (Ⅲ) is -NH on the side chain amino silicone oil 2 The group reacts with the double bond fluorine atom of the hexafluoropropylene trimer to undergo a nucleophilic substitution reaction to synthesize a fluorosilicone polymer as shown in the general structural formula (Ⅷ).

[0048] (Ⅷ):

[0049] Concrete reaction steps are as follows:

[0050] Add 70ml of ethylene glycol dimethyl ether, 1.7g of triethylamine, and 40g of side chain amino silicone oil shown in formula (III) to the reaction flask in sequence, and stir under nitrogen protection, and add 7.4 g of hexafluoropropylene trimer dropwise at room temperature. g. Control the dropping time for 30 minutes. After the dropping, add 30ml of ethylene glycol dimethyl ether to maintain ro...

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Abstract

The invention discloses an organic fluorine-silicon surface treatment agent and a preparation method thereof. According to the organic fluorine-silicon surface treatment agent, amino silane coupling agents, amino-polysiloxane and epoxy polysiloxane serve as basic reactants, hexafluoropropene trimer serves as a modifying agent, glycol dimethyl ether serves as solvent, triethylamine serves as a catalyst, and the organic fluorine-silicon surface treatment agent is a fluorine-silicon oxidane compound synthesized through a reaction or a fluorine-silicon oxidane polymer with a perfluoroalkyl group introduced to a side chain. According to the organic fluorine-silicon surface treatment agent and the preparation method thereof, it is not needed to generate a reaction intermediate through a link chain structure in the first place, the synthesis route is simple, the conversion rate is high, and the prepared organic fluorine-silicon compound has high surface activity and high stability and can be used for water resistance, oil resistance and stain repellent finishing of fiber fabric as well as waterproof and stain repellent treatment of metal and building materials.

Description

technical field [0001] The invention relates to an organic fluorosilicon compound, in particular to an organic fluorosilicon surface treatment agent and a preparation method thereof. Background technique [0002] Due to its unique low surface tension and chemical stability, fluorosilicone surfactants are widely used in various fields such as material protection, architectural coatings, textiles, industrial cleaning, fire extinguishing and pesticides. For example, the reaction product of fluorosilicone can be used as a surface treatment agent for textiles and other materials, endowing the material with excellent water repellency, oil repellency, stain resistance and tactility. In order to simultaneously provide water and oil repellency and softness to substrates such as textiles, a water and oil repellent composition comprising a provided perfluoroalkyl group and a softness-providing silicone compound has been widely used. At present, the synthesis of organofluorosilicon sur...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G77/385C07F7/18D06M13/513D06M15/643
Inventor 陶海峰雷志涛徐山山
Owner ZHEJIANG HAPPY CHEM
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