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Benzocyclobutene monomers containing siloxane and imide structure and synthesis and application thereof

A technology of benzocyclobutene and synthesis method, which is applied in chemical instruments and methods, compounds of group 4/14 elements of the periodic table, organic chemistry, etc., and can solve the problems of high water absorption, high dielectric constant, polyimide The problem of amine refractory/solubility has been solved, and the effects of high production efficiency, pure product and simple preparation method have been achieved.

Active Publication Date: 2012-06-20
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the large rigidity and high polarity of the imide ring make most polyimides have problems such as refractory / solubility, darker color, high dielectric constant, and high water absorption, which seriously restricts Its scope of application

Method used

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  • Benzocyclobutene monomers containing siloxane and imide structure and synthesis and application thereof
  • Benzocyclobutene monomers containing siloxane and imide structure and synthesis and application thereof
  • Benzocyclobutene monomers containing siloxane and imide structure and synthesis and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Example 1 Synthesis of monomer BCB-SiO-0 (I, n=0):

[0022] (a) 1.34 g (0.01 mol) of 1,1,3,3-tetramethyldisiloxane, 3.28 g (0.02 mol) of 5-norbornene-2,3-dioic anhydride and 0.032 mL of Karstedt catalyst ( Pt, ~2%) was dissolved in 10mL of toluene, stirred and reacted at 110°C for 15 hours. After the reaction solution was cooled to room temperature, 0.4 g of activated carbon was added, and stirring was continued for 0.5 hours. After filtration, toluene solvent was distilled off under reduced pressure, washed twice with anhydrous diethyl ether (2*10 mL), and vacuum-dried at 80°C for 4 hours to obtain 3.5 g of a viscous product with a yield of 75.6%.

[0023] 1 H NMR (500 MHz, CDCl 3 ) δ: 0.05-0.08 (m, 12H), 0.65 (t, 2H), 1.55-1.68 (m, 8H), 2.72-2.9 (m, 4H), 3.41-3.45(m, 4H). FTIR (KBr) : 1857 and 1775cm -1 (anhydride, ν C=O ), 1224cm -1 (ν C-Si ), 1084cm -1 (ν Si-O-Si ).

[0024] (b) Add the product obtained in step (a) (1.26g, 10.58mmol), 4-aminobenzocyclo...

Embodiment 2

[0026] Example 2 Synthesis of monomer BCB-SiO-6 (I, n≈6):

[0027] (a) 5.76 g of hydrogen-terminated polysiloxane (molecular weight ≈580 g / mol), 3.28 g (0.02 mol) of 5-norbornene-2,3-diacid anhydride, and 0.032 mL of Karstedt catalyst (Pt, ~2% ) was dissolved in 10 mL of toluene, stirred and reacted at 110°C for 14 hours. After the reaction solution was cooled to room temperature, 0.5 g of activated carbon was added, and stirring was continued for 0.5 hours. After removing the activated carbon by filtration, distilling off the toluene solvent under reduced pressure, washing with anhydrous diethyl ether (2*10 mL), and vacuum drying at 80°C for 4 hours, 7.0 g of a viscous product was obtained, with a yield of 77.1%.

[0028] 1 H NMR (500 MHz, CDCl 3) δ: 0.05-0.11 (m, 55H), 0.66 (t, 2H), 1.54-1.80 (m, 8H), 2.81-2.85 (d, 4H), 3.41-3.58(m, 4H). FTIR (KBr) : 1859 and 1782cm -1 (anhydride, ν C=O ), 1222cm -1 (ν C-Si ), 1087cm -1 (ν Si-O-Si ).

[0029] (b) Add the produc...

Embodiment 3

[0031] Example 3 Curing of monomer BCB-SiO-0 (I, n=0):

[0032] A certain amount of powdered monomer BCB-SiO-0 synthesized in Example 1 was dissolved in a small amount of CH 2 Cl 2 solvent, which is then injected into specific molds. Remove CH by volatilization at 100°C 2 Cl 2 Finally, the reaction was carried out according to the following conditions: 210°C / 1h, 250°C / 1h, 270°C / 1h, and a light yellow resin with mechanical properties was obtained. The resin structure is characterized as follows: FTIR (KBr): 1776 and 1713cm -1 (ν C=O ), 1373cm -1 (ν C-N ), 1501cm -1 (δ C-H ). Thermogravimetric analysis: The initial thermal decomposition temperature (1% weight loss) of the cured resin is 468°C.

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Abstract

The invention belongs to the technical field of polymer dielectric materials and in particular relates to benzocyclobutene monomers containing siloxane and imide structure and a synthesis method and application of the Benzocyclobutene monomers. Hydrosilylation reaction is allowed to take place between hydrogen-terminated polysiloxane / siloxane and 5-norbornylene-2,3-dianhydride in the presence of platinum catalysts to produce an intermediate compound, and imidization reaction is allowed to take place between the intermediate compound and 4-aminobenzocyclobutene to obtain the target monomers. The monomers have good solubility, and can be directly formed by thermal polymerization or dissolved in solvents to make films by spin-coating, followed by curing. The polymerization process is simple and free of byproducts. The cured resins have the characteristics of good heat resistance, low dielectric constant and low hydroscopicity; and the mechanical properties of the cured resins can be regulated by changing siloxane structure.

Description

technical field [0001] The invention belongs to the technical field of polymer dielectric materials, in particular to a synthesis method and application of a class of benzocyclobutene monomers containing siloxane and imide structures and resins thereof. Background technique [0002] The presence of imide structure endows polyimide (PI) materials with excellent heat resistance, chemical stability and mechanical properties. Therefore, PI has been widely used in aerospace, automobile industry, electronics industry and many other fields. However, the large rigidity and high polarity of the imide ring make most polyimides have problems such as refractory / solubility, dark color, high dielectric constant, and high water absorption, which seriously restricts its scope of application. For this reason, the modification of PI has been widely concerned. Among them, the performance of polyimide containing siloxane structure has been improved in terms of solubility, adhesion, hygroscopi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/10C08G77/388C08J3/24C08G61/12
Inventor 杨军肖斐
Owner FUDAN UNIV
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