Preparation methods of benzocyclobutene functionalized cage type polysilsesquioxane (POSS) and resins of benzocyclobutene functionalized cage type polysilsesquioxane

A benzocyclobutene functional, polysilsesquioxane technology, applied in the direction of coating, can solve problems such as limiting the application of materials, and achieve the effects of low dielectric properties, excellent heat resistance, and high thermal stability

Inactive Publication Date: 2017-11-07
SOUTHWEAT UNIV OF SCI & TECH
4 Cites 8 Cited by

AI-Extracted Technical Summary

Problems solved by technology

[0007] In the prior art, there are many reports on benzocyclobutene resins abroad, such as: U.S.Pat.5882836, 1999; Journal of Polymer Science, Part A: Polymer Chemistry, 2011, 49, 381-391; Chinese patent CNL200710111698. 4 etc. U.S. Patent (U.S.Pat.5882836, 1999) utilizes 4-bromobenzocyclobutene and tetramethyldivinyldisiloxane to bridge the tetramethyldivinylsiloxane prepared by HECK reaction The benzocyclobutene (...
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Method used

Above-mentioned embodiment 31~34 the present invention is with BCB-POSS as adding, joins in DVSBCB, because there is common group BCB, after curing, POSS can be well dispersed in the material, optimizes material effectively electrical properties.
[0122] The above-mentioned embodiments 18-21 can effec...
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Abstract

The invention discloses preparation methods of benzocyclobutene functionalized cage type polysilsesquioxane (POSS), shown in a formula (IV), and resins of the benzocyclobutene functionalized cage type POSS. The preparation method of the benzocyclobutene functionalized cage type POSS comprises the steps of adding a toluene solution of OVPOSS and 4-(1,1-dimethyl-1-hydrogen)silicon-base benzocyclobutene into a reactor, replenishing the reactor with nitrogen for protecting, adding a tetrahydrofuran solution of chloroplatinic acid, carrying out a reaction at the temperature of 60-90 DEG C, separating and purifying the materials obtained after the reaction is finished so as to obtain the benzocyclobutene functionalized cage type POSS. The benzocyclobutene functionalized cage type POSS can be further prepared into body polymers or solution polymers, and can be added into matrix resins so as to form nano composite materials. According to the preparation methods, the POSS is cleverly introduced into the benzocyclobutene resin by means of a simple and efficient hydrosilylation reaction. The resins prepared by the methods provided by the invention have excellent heat stability, mechanical properties and electrical properties, thus being suitable for being used as interlayer dielectric films or packaging materials in the fields such as micro-electronics industry and national defense aerospace. The formula (IV) is described in the description.

Application Domain

Technology Topic

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  • Preparation methods of benzocyclobutene functionalized cage type polysilsesquioxane (POSS) and resins of benzocyclobutene functionalized cage type polysilsesquioxane
  • Preparation methods of benzocyclobutene functionalized cage type polysilsesquioxane (POSS) and resins of benzocyclobutene functionalized cage type polysilsesquioxane
  • Preparation methods of benzocyclobutene functionalized cage type polysilsesquioxane (POSS) and resins of benzocyclobutene functionalized cage type polysilsesquioxane

Examples

  • Experimental program(41)

Example Embodiment

[0050] Example 1:
[0051] Benzocyclobutene functionalized cage polysilsesquioxane is characterized in that the compound has the chemical structural formula shown in (IV):
[0052]
[0053] Where:
[0054]
[0055] 0 1 <8, R+R 1 = 8.

Example Embodiment

[0056] Example 2:
[0057] The preparation method of cage type [1,1-dimethyl,1-(4'-benzocyclobutenyl)silylethyl]vinylsilsesquioxane (abbreviated as BCB-POSS), the steps are: dry Add 6.33g cage octaethylene silsesquioxane (OVPOSS) to the anaerobic bottle equipped with a magnetic stirrer. Blow nitrogen for 10 minutes to remove the oxygen in the system. Add [4-(1,1- (Dimethyl-1-hydrogen))silylbenzocyclobutene (4-DMHSBCB for short) 16.2g, (catalyst) H with a molar concentration of 0.025M 2 PtCl 6 100 μL of the tetrahydrofuran solution and 50 mL of toluene, the mixture was reacted at 80° C. for 72 hours under a nitrogen atmosphere, and thin-layer chromatography monitored whether the reaction of the reaction raw material OVPOSS was complete. After the reaction, cool the reacted material to room temperature, add ethanol 5 times the mass of the reacted material, precipitate, and filter; add 5 times the mass of the reacted material to the solid obtained after filtration, precipitate and filter; Then add ethanol 5 times the mass of the reacted material to the solid obtained after the reaction, precipitate, and filter; the solid obtained after filtration (ie, the precipitate) is placed in a vacuum drying oven at a pressure of -0.09~-0.095MPa and a temperature of 80 After drying for 20 hours at ℃, a paste product is obtained, namely the prepared cage-type [1,1-dimethyl,1-(4'-benzocyclobutenyl)silylethyl]vinylsilsesquioxane ( Referred to as BCB-POSS), the yield is 85%.
[0058] The structure is characterized as follows: infrared spectrum IR (KBr coating film, cm-1): 3058, 3019, 2962, 2227, 1595, 1462, 1400, 1295, 1253, 1092, 1021, 881, 799.4, 633; 1 H NMR(600MHz, CDCl 3 )δ:0.33-0.41(6H,-SiCH 3 ),0.69-1.11(4H,-SiCH 2 -), 3.27(4H, -CH 2 -),5.7-6.1(n,-SiC 2 H 5 ), 7.12-7.45 (3H, -ArH).

Example Embodiment

[0059] Example 3:
[0060] The preparation method of cage type [1,1-dimethyl,1-(4'-benzocyclobutenyl)silylethyl]vinylsilsesquioxane (abbreviated as BCB-POSS), the steps are: dry Add 6.33g cage octaethylene silsesquioxane (OVPOSS for short) into an anaerobic bottle equipped with a magnetic stirrer. Blow nitrogen for 30 minutes to remove oxygen in the system. Add [4-(1,1- (Dimethyl-1-hydrogen)]silyl benzocyclobutene (4-DMHSBCB for short) 24.3g, (catalyst) H with a molar concentration of 0.025M 2 PtCl 6 200 μL of the tetrahydrofuran solution and 60 mL of toluene, the mixture was reacted at 85° C. for 60 hours under a nitrogen atmosphere, and the reaction material OVPOSS was monitored by thin layer chromatography to see if the reaction was complete. After the reaction, cool the reacted material to room temperature, add ethanol of 10 times the mass of the reacted material, precipitate, and filter; add ethanol to the solid obtained after filtration with 10 times the mass of the reacted material, precipitate and filter; Then add ethanol 10 times the mass of the reacted material to the solid obtained after the reaction, precipitate and filter; the solid obtained after filtration (ie, the precipitate) is placed in a vacuum drying oven at a pressure of -0.09~-0.095MPa and a temperature of 90 After drying for 12 hours at ℃, a paste product is obtained, namely the prepared cage-type [1,1-dimethyl,1-(4'-benzocyclobutenyl)silylethyl]vinylsilsesquioxane ( Referred to as BCB-POSS), the yield is 88%.
[0061] The structure is characterized as follows: infrared spectrum IR (KBr coating film, cm-1): 3058, 3019, 2962, 2227, 1595, 1462, 1400, 1295, 1253, 1092, 1021, 881, 799.4, 633; 1 H NMR(600MHz, CDCl 3 )δ:0.33-0.41(6H,-SiCH 3 ),0.69-1.11(4H,-SiCH 2 -), 3.27(4H, -CH 2 -),5.7-6.1(n,-SiC 2 H 5 ), 7.12-7.45 (3H, -ArH).
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PUM

PropertyMeasurementUnit
Thermal decomposition temperature495.0°C
tensileMPa
Particle sizePa
strength10

Description & Claims & Application Information

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