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Synthesis method of siloxane-substituted maleimide

A technology of maleimide and alkyl siloxane, which is applied in the field of polymer monomer synthesis, can solve the problems of easy hydrolysis of siloxane and cumbersome synthesis process, etc. convenient effect

Inactive Publication Date: 2015-03-25
SHANGHAI AIMO JINSHAN PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method has disadvantages such as cumbersome synthesis process and easy hydrolysis of siloxane in the dehydration process. Therefore, it is necessary to develop a new synthesis method

Method used

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  • Synthesis method of siloxane-substituted maleimide
  • Synthesis method of siloxane-substituted maleimide
  • Synthesis method of siloxane-substituted maleimide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] The synthesis of embodiment 11-bromopentyltrimethoxysilane

[0029]

[0030] In an argon atmosphere, add trimethoxysilane (24.00g, 0.20mol) and bromopentene-1 (BrCH 2 CH 2 CH 2 CH=CH 2 ) (30.00g, 0.20mol) of the mixed solution, drop 30 drops of Karstedt catalyst (isopropanol solution of chloroplatinic acid). The mixture was heated to 80°C and maintained at this temperature for 24 hours. The obtained reaction mixture was quickly distilled under reduced pressure (below 100° C.) to obtain the target product with a yield of 30%. 1 H NMR (400MHz, CDCl 3 ,293K)δ:3.56(s,9H,OCH 3 ),3.37-3.42(s,2H,-CH 2 -Br),1.82-1.86(s,2H,-CH 2 -CH 2 -Br),1.38-1.45(s,4H,Si-CH 2 CH 2 CH 2 ),0.62-0.64(s,2H,Si-CH 2 ).

Embodiment 21

[0031] The synthesis of embodiment 21-bromohexyl triethoxysilane

[0032]

[0033] In an argon atmosphere, add trimethoxysilane (22.00 g, 0.18 mol) and bromohexene-1 (BrCH 2 CH 2 CH 2 CH 2 CH=CH 2 ) (30.00g, 0.18mol) of the mixed solution, drop 30 drops of Karstedt catalyst (isopropanol solution of chloroplatinic acid). The mixture was heated to 80°C and maintained at this temperature for 24 hours. The obtained reaction mixture was quickly distilled under reduced pressure (less than 100° C.) to obtain the target product with a yield of 35%. 1 H NMR (400MHz, CDCl 3 ,293K)δ:3.56(s,9H,OCH 3 ),3.37-3.42(s,2H,-CH 2 -Br),1.82-1.86(s,2H,-CH 2 -CH 2 -Br),1.38-1.45(s,6H,Si-CH 2 CH 2 CH 2 CH 2 ),0.62-0.64(s,2H,Si-CH 2 ).

Embodiment 31

[0034] Synthesis of Example 31-Bromododecyltrimethoxysilane

[0035] The synthesis of A, bromododecene-1

[0036]

[0037] Under cooling in an ice bath, bromohexene-1 (Br(CH 2 ) 4 CH=CH 2 ) (40.00g, 0.31mol), the addition was completed, and the mixture was stirred for 30 minutes under ice-bath cooling. The obtained Grignard reagent was transferred to the dropping funnel and slowly dropped into an ice-bath cooled mixture consisting of: Br(CH 2 ) 6 Br (77.4g, 0.4mol), Li 2 CuCl 4(0.1M solution in THF, 20ml) and THF (100ml). After dropping, the reaction mixture was further stirred for 30 minutes under cooling in an ice bath, and then the solvent was removed by evaporation. The obtained residue was treated with dilute hydrochloric acid and then extracted with n-hexane. After removal of the solvent, the crude product was obtained as an oil. Rectification under reduced pressure gave the pure product with a yield of 60%. 1 H NMR (400MHz, CDCl 3 ,293K)δ:5.75-5.85(s,1H,C...

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Abstract

The invention belongs to the field of synthesis of polymer monomers, and specifically relates to a synthesis method of siloxane-substituted maleimide which can be used as an active coupling agent of glass fibers for greatly improving the combination force of the glass fibers and organic resins. The traditional manufacturing method of such coupling agent is a two-step method and comprises the steps of enabling amino alkyl siloxane and maleic anhydride to react to generate maleamic acid alkyl siloxane; synthesizing the siloxane-substituted maleimide through amic acid under the effect of a dehydrating agent. The invention provides a novel synthesis method for preparing a target product through raw materials that are alkali metal salt of maleimide and halogen alkyl siloxane by an one-step mode in the presence of a polar aprotic solvent, aims at overcoming the shortages that the traditional synthesis method is cockamamie in process and the dehydrating easily leads to hydrolyzing of siloxane. The method, by being compared with the traditional synthesis method, has the advantages that the after-treatment is convenient, the siloxane is avoided electrolyzing, and the product is high in purity.

Description

technical field [0001] The invention belongs to the field of macromolecular monomer synthesis, and in particular relates to a method for synthesizing maleimides substituted by alkyl siloxanes. Background technique [0002] As an effective surface treatment agent for glass fibers and fillers, silane coupling agents have been widely used in glass fiber manufacturing, rubber and plastic processing industries. In recent years, with the development of nanotechnology, silane coupling agents have been valued as surface coating agents for certain nanoparticles. [0003] The chemical structure of the silane coupling agent is that one end of the molecule is siloxane, and the other end is a long-chain alkyl group with active functional groups (epoxy, amino and vinyl). Through hydrolysis, the silane coupling agent can form an oligomer (or sol) that has a certain molecular weight but is still soluble in the solvent. Using such an oligomer to treat glass fiber or silica can pass siloxane...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/18
Inventor 姜标
Owner SHANGHAI AIMO JINSHAN PHARM CO LTD
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