Silicon-containing aromatic diamine and preparation method thereof

An aromatic binary, hydrosilation reaction technology, applied in chemical instruments and methods, compounds of periodic table Group 4/14 elements, organic chemistry, etc., can solve and/or synthetic methods are complicated to operate and difficult to scale industrial Production, three wastes and other serious problems, to achieve the effect of high industrial production value, convenient synthesis of similar compounds, and mild conditions

Inactive Publication Date: 2015-08-26
QUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] Therefore, the existing silicon-containing aromatic diamines have poor performance, and/or the synthesis method is compl...

Method used

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  • Silicon-containing aromatic diamine and preparation method thereof
  • Silicon-containing aromatic diamine and preparation method thereof
  • Silicon-containing aromatic diamine and preparation method thereof

Examples

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Embodiment 1

[0028] Embodiment 1 The synthesis of methylphenyl bis (4-aminophenethyl) silane

[0029] At 0°C, slowly add a mixture of 12.2g (0.10mol) of methylphenylsilane and 50mL of toluene dropwise to 4mL of 2.0mM isopropanol solution of chloroplatinic acid and 26.2g (0.22mol) of 4-vinylaniline 80mL of toluene solution, stirred at 25°C for 16h, evaporated the solvent under reduced pressure, and recrystallized the residue from butyl acetate to obtain 34.3g of methylphenylbis(4-aminophenethyl)silane as a light off-white solid product. The rate is 95.3%, and the content is 98.4%. Elemental analysis measured value (calculated value) / %: C 76.88 (76.67), H 7.85 (7.78), N 7.91 (7.78). MS (m / z): 361 [M+H] + .

Embodiment 2

[0030] Example 2 Synthesis of diphenyl di(3-aminophenethyl)silane

[0031] At 5°C, a mixture of 18.4g (0.10mol) of diphenylsilane and 50mL of benzene was slowly added dropwise to a 100mL benzene solution containing 1.2g of platinum dioxide and 26.2g (0.22mol) of 3-vinylaniline, The reaction was stirred at 20°C for 20 hours, the solvent was evaporated under reduced pressure, and the residue was recrystallized from ethyl lactate to obtain 39.5 g of off-white solid product diphenylbis(3-aminophenethyl)silane, with a yield of 93.6% and a content of 98.6% . Elemental analysis measured value (calculated value) / %: C 79.77 (79.62), H 7.32 (7.11), N 6.78 (6.64). MS (m / z): 423[M+H] + .

Embodiment 3

[0032] Example 3 Synthesis of methyl (3,3,3-trifluoropropyl) bis (3-aminophenethyl) silane

[0033] At 0°C, a mixture of 14.2 g (0.10 mol) of methyl (3,3,3-trifluoropropyl) silane and 60 mL of dichloromethane was slowly added dropwise to 1,3-divinyl-1,1 , 1.2g of 3,3-tetramethyldisiloxane platinum and 27.4g (0.23mol) of 3-vinylaniline in 80mL of dichloromethane solution, stirred and reacted at 20°C for 15h, evaporated the solvent under reduced pressure, and the residue Recrystallized from dimethyl carbonate to obtain 37.0 g of off-white solid product methyl(3,3,3-trifluoropropyl)bis(3-aminophenethyl)silane, with a yield of 97.3% and a content of 98.2%. Elemental analysis measured value (calculated value) / %: C 62.99 (63.16), H 7.00 (7.11), N 7.56 (7.37). MS (m / z): 381 [M+H] + .

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Abstract

The invention provides silicon-containing aromatic diamine and a preparation method thereof. Di-substituted silane and 4-vinylaniline or 3-aminostyrene are taken as raw materials and have a hydrosilation one-pot reaction under the action of a platinum catalyst, and di-substituted di(amino-phenethyl) silane is prepared. In the compound, two benzene rings containing amino are linked with the same silicon atom through two carbon atoms respectively, and the compound has excellent flexibility, flame retardancy and heat resistance. A synthetic process has the characteristics of easiness in obtaining of raw materials, simplicity in operation, mild conditions, high product yield, low cost, environmental protection and the like, and silicon-containing aromatic diamine has higher industrial production value.

Description

technical field [0001] The invention relates to a silicone material monomer containing silicon-containing aromatic diamine and a preparation method thereof. Background technique [0002] Due to the excellent heat resistance, flexibility and flame retardancy of silicon-containing materials, silicon-containing polymer material monomers such as silicon-containing diamines, dihydric phenols, and dibasic acids can be used in polyamides and polyimides. Introducing silicon element into materials such as polyester, polycarbonate, and epoxy resin to obtain chemically modified new polymer materials is an important development direction of the organic silicon industry and the polymer material industry. [0003] Aromatic diamines such as p-phenylenediamine, 4,4'-biphenylenediamine, diaminodiphenyl ether, 4,4'-diaminodiphenylmethane, etc., are widely used in the preparation of aromatic polyamides, aromatic Materials such as polyimide are also commonly used as curing agents for epoxy res...

Claims

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Application Information

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IPC IPC(8): C07F7/10C07F7/12C08G59/50
Inventor 郑土才潘向军赵芝清李杰金懿吕延文
Owner QUZHOU UNIV
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