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Fluorosilicone acrylate and preparation method thereof

A technology of fluorosilicon acrylate and polyfluoroalkyl silicon acrylate, which is applied in the field of synthesis of acrylate monomers and polymer materials, and can solve the problem of carbon-carbon double bond free radicals that do not have the characteristics of densely packed fluorine-containing alkyl groups. Insufficient polymerization reactivity, poor accumulation density of fluorine-containing alkyl groups, etc., achieve the effect of simple equipment requirements, realization of anti-repellent function, significant and effective anti-repellent function

Inactive Publication Date: 2015-10-14
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are also acrylic acid esters such as fluorine-containing alkyl itaconate and fluorine-containing alkyl butenedioic acid esters that have been reported. The multiple fluoroalkyl groups of these monomers are bonded to each other through structures such as ethylene groups as bridging groups. In the enolate structure, the density of the fluorine-containing alkyl group is poor
Chinese invention patent "a fluorine-silicon modified acrylate adhesive and its preparation method and application" (CN103224765A) discloses a fluorine-containing silicone unsaturated monomer, and the provided vinyl-terminated fluorine-containing polysilicon Although oxane bonds the fluoroalkyl group to the molecular structure of the monomer through the silicon atom, because the fluoroalkyl group is not bonded to the same silicon atom, it does not have the structural characteristics of densely packed fluoroalkyl groups
And the unsaturated group used in the fluorine-containing silicone unsaturated monomer is silicon vinyl (Si-CH=CH 2 ), its carbon-carbon double bond radical polymerization reactivity is much lower than that of acrylates, so when using monomers to prepare fluoropolymer emulsions, the conventional polymerization process cannot completely react and obtain stable emulsions

Method used

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  • Fluorosilicone acrylate and preparation method thereof
  • Fluorosilicone acrylate and preparation method thereof
  • Fluorosilicone acrylate and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] 1. Hydrosilylation reaction

[0026] In a three-necked flask equipped with magnetic stirring, a thermometer and a reflux condenser, add 6.31 grams of allyl methacrylate, 0.005 grams of chloroplatinic acid and 20 grams of toluene, stir to dissolve, raise the temperature to 70 ° C, and drop it within 1 hour 5.20 g of dimethyl monochlorohydrogen silane. After reacting at 70° C. for 3 hours, the reaction was stopped. The solvent toluene and unreacted dimethyl monochlorohydrosilane were distilled off under reduced pressure, the distillation temperature was 40° C., and the vacuum degree was 15 mmHg to obtain a silicon-containing acrylate intermediate. FT-IR (KBr): 2956.4, 2892.7, 1720.0, 1635.4, 1453.1, 1256.3, 1166.7, 1055.7, 842.3 cm -1 . 1 H NMR (400 MHz, CDCl 3 ): δ 6.10 (C H H=CCH 3 ), 5.56 (CH H =CCH 3 ), 4.13 (SiCH 2 CH 2 C H 2 ), 1.94 (CH 2 =CC H 3 ), 1.78 (SiCH 2 C H 2 CH 2 ), 0.88 (SiC H 2 CH 2 CH 2 ), 0.43 (SiC H 3 ).

[0027] 2. Fluoroalk...

Embodiment 2

[0035] 1. Hydrosilylation reaction

[0036] In a three-necked flask equipped with magnetic stirring, a thermometer and a reflux condenser, add 5.6 grams of allyl acrylate, 0.005 grams of chloroplatinic acid and 20 grams of toluene, stir to dissolve, raise the temperature to 70 ° C, and drop the first formazan within 1 hour 6.90 grams of dichlorohydrogensilane. After reacting at 70° C. for 3 hours, the reaction was stopped. The solvent toluene and unreacted monomethyldichlorohydrogensilane were distilled off under reduced pressure at a distillation temperature of 40° C. and a vacuum of 15 mmHg to obtain a silicon-containing acrylate intermediate. FT-IR (KBr): 2959.7, 2931.4, 2891.9, 1720.0, 1637.1, 1453.1, 1261.1, 1166.6, 799.0 cm -1 . 1 H NMR (400 MHz, CDCl 3 ): δ 6.11 (C H H=CCH 3 ), 5.57 (CH H =CCH 3 ), 4.15 (SiCH 2 CH 2 C H 2 ), 1.94 (CH 2 =CC H 3 ), 1.87 (SiCH 2 C H 2 CH 2 ), 1.16 (SiC H 2 CH 2 CH 2 ), 0.76 (SiC H 3 ).

[0037] 2. Fluoroalkylation...

Embodiment 3

[0045] 1. Hydrosilylation reaction

[0046] In a three-necked flask equipped with magnetic stirring, a thermometer and a reflux condenser, add 6.50 grams of allyl methacrylate, 0.01 grams of chloroplatinic acid and 15 grams of xylene, stir to dissolve, raise the temperature to 72 ° C, drop in 1.5 hours Complete 7.60 g of trichlorohydrogensilane. After reacting at 72° C. for 3 hours, the reaction was stopped. The solvent xylene and unreacted trichlorohydrosilane were distilled off under reduced pressure at a distillation temperature of 50° C. and a vacuum of 10 mmHg to obtain a silicon-containing acrylate intermediate. FT-IR (KBr): 2958.8, 2929.4, 2895.4, 1720.1, 1636.4, 1452.9, 1262.1, 1167.1, 1043.8, 815.8 cm -1 .

[0047] 2. Fluoroalkylation reaction

[0048] In a three-necked flask equipped with magnetic stirring, a thermometer and a reflux condenser, add 49.05 grams of 3,3,4,4,5,5,6,6,6-nonafluorobutylbromoethane, 10.8 grams of magnesium chips and 240 grams of tetrahydr...

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Abstract

The invention discloses fluorosilicone acrylate and a preparation method thereof, and specifically relates to polyfluoroalkylsilicone acrylate or polyfluoroalkylsilicone methacrylate and a preparation method thereof. According to the technical scheme of the invention, allyl enoate reacts with hydroxyl chlorosilane, such that silicon-containing acrylate is prepared through a hydrosilylation reaction; fluorine-containing alkyl magnesium bromide is subjected to a reaction with silicon-containing acrylate, such that fluorosilicone acrylate is obtained through fuoroalkylation. The obtained fluorosilicone acrylate contains a carbon-carbon double bond facilitating free radical polymerization and free radical copolymerization, and can be used for preparing a fluorine-containing polymer under a mild reaction condition. The monomer molecule of fluorosilicone acrylate comprises a plurality of fluoroalkyl groups in a densely packed state, such that the prepared polymer can provide a better resisting effect. The fluorosilicone acrylate preparation method has the advantages of simple process, mild reaction conditions, and low equipment requirement. The method is suitable for industrialized productions.

Description

technical field [0001] The invention relates to a fluoroalkyl silicon acrylate and a preparation method thereof, in particular to a fluoroalkyl silicon acrylate monomer and a preparation method thereof, and belongs to the field of synthesis of acrylate monomers and polymer materials. Background technique [0002] Acrylic acid ester monomers are an important monomer in the synthesis of water and oil repellent materials, and fluorine-containing acrylate monomers have excellent surface properties and repellent functions and are widely used. The polymerized double bond is the main raw material for the synthesis of fluorine-containing polymers. [0003] It is precisely because of the fluoroalkyl groups contained in the side chains of fluoropolymers, these fluoroalkyl groups protect and shield the polymer main chain with a zigzag chain structure, so that the polymer film has low surface energy, thus providing excellent water and oil repellency Function. Increasing the carbon cha...

Claims

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Application Information

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IPC IPC(8): C07F7/08
Inventor 蔡露李战雄臧雄袁艳华
Owner SUZHOU UNIV