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Silicon-containing benzoxazine resin as well as preparation method and application thereof

A benzoxazine and benzoxazine-based technology, which is applied in the field of benzoxazine resin-silicon-containing benzoxazine monomers and polymers, can solve the problem of polycyclic benzoxazine synthesis, which has not been reported yet, etc. problems, to achieve excellent heat resistance, low surface energy, and good hydrophobicity

Active Publication Date: 2011-07-27
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] However, the above-mentioned synthesis of polybenzoxazine modified with silicone resin mainly focuses on the synthesis of monocyclic benzoxazine monomers based on monohydric phenols, and the synthesis of polycyclic benzoxazines based on polyhydric phenols has not been reported yet.

Method used

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  • Silicon-containing benzoxazine resin as well as preparation method and application thereof
  • Silicon-containing benzoxazine resin as well as preparation method and application thereof
  • Silicon-containing benzoxazine resin as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0078] Example 1 Bis(3-triethoxysilane-n-propyl-3,4-dihydro-2H-1,3-benzoxazinyl)isopropane (BZB-550)

[0079] Add 15 mL of chloroform and 3.2 g (0.1 mol) of paraformaldehyde into a 100 mL three-necked flask in sequence, and stir evenly. Dissolve 11.0g of γ-aminopropyltriethoxysilane (KH-550) (0.05mol) in 12mL of chloroform, stir evenly and add it to the paraformaldehyde solution, heat up to 85°C for 10min, add 5.7g ( 0.025mol) bisphenol A, reflux for 3h. The generated water was removed by liquid separation, and the solvent was removed by rotary evaporation to obtain a colorless and transparent liquid with a yield of 84%.

[0080] Elemental Analysis: C 37 h 62 N 2 o 8 Si 2 , % of theory: C, 61.8%; H, 8.69%; N, 3.9%. Analytical values: C, 62.1%; H, 8.44%; N, 3.84%.

[0081] That 1 H NMR spectrum as figure 1 As shown, the FTIR spectrum is as figure 2 shown.

[0082] 1 H NMR (CDCl 3 , 300MHz, δ): 3.93ppm (s, Ar-CH 2 -N), 4.82ppm (s, O-CH 2 -N), 1.59ppm(-C(CH 3 )...

Embodiment 23

[0083] Example 23-(Methyl-dimethoxysilane)-n-propyl-3,4-dihydro-2H-1,3-benzoxazine (BZS-660)

[0084] 15 mL of dioxane and 3.2 g (0.1 mol) of paraformaldehyde were successively added into a 100 mL three-necked flask, and stirred evenly. Dissolve 8.16g of γ-aminopropylmethyldimethoxysilane (KH-660) (0.05mol) in 12mL of dioxane, stir evenly and add it to the paraformaldehyde solution, raise the temperature to 90°C for 10min, add 4.7g (0.05mol) of phenol was refluxed for 3h. The generated water was removed by liquid separation, and the solvent was removed by rotary evaporation to obtain a colorless and transparent liquid with a yield of 86%.

[0085] Elemental Analysis: C 14 h 23 NO 3 Si, theoretical %: C, 59.75%; H, 8.24%; N, 4.98%; Analytical values: C, 61.1%; H, 8.06%, N, 4.87%.

[0086] Its FTIR spectrum is as Figure 4 shown.

[0087] 1H NMR (CDCl3, 300MHz, δ): 3.95ppm (s, Ar-CH2-N), 4.86ppm (s, O-CH2-N), 2.64-2.769ppm (t, N-CH2-C), 1.60- 1.62(m, C-CH2-C), 0.68-0.74(...

Embodiment 3

[0088] Example 3 Bis(3-methyl-dimethoxysilane-n-propyl-3,4-dihydro-2H-1,3-benzoxazinyl)isopropane (BZB-660)

[0089] Add 15 mL of chloroform and 7.8 mL (0.1 mol) of formaldehyde solution to a 100 mL three-neck flask in sequence, and stir evenly. Dissolve 8.16g of KH-660 (0.05mol) in 12mL of chloroform, stir evenly and add it to the paraformaldehyde solution, heat up to 85°C for 10min, add 5.7g (0.025mol) of bisphenol A, and reflux for 3h. The generated water was removed by liquid separation, and the solvent was removed by rotary evaporation to obtain a colorless and transparent liquid with a yield of 82%.

[0090] Elemental Analysis: C 31 h 50 N 2 o 6 Si 2 , Theoretical %: C, 61.76%; H, 8.36%; N, 4.65%; Analytical value: C, 61.62%; H, 8.246%; N, 4.78%.

[0091] Its FTIR spectrum is as Figure 5 shown.

[0092] 1 H NMR (CDCl 3 , 300MHz, δ): 3.95ppm (s, Ar-CH 2 -N), 4.86ppm (s, O-CH 2 -N), 1.59ppm(-C(CH 3 ) 2 -), 2.64-2.769ppm (t, N-CH 2 -C), 1.60-1.62(m, C-CH 2 ...

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Abstract

The invention discloses a silicon-containing benzoxazine resin. A monomer of the silicon-containing benzoxazine resin is synthesized through Mannich reaction according to theoretical mole ratio by taking phenols compounds, formaldehyde and amine compounds as reactive raw materials; and a polymer of the silicon-containing benzoxazine resin is obtained by carrying out hydrolytic condensation and heating ring-opening polymerization reaction on the monomer. Silicon-containing benzoxazine has higher carbon residual rate, glass transition temperature and silicon content and lower surface energy, thereby having potential application prospect in preparing ablation resisting materials, heat resisting material, flame-retardant materials and waterproof materials; and in addition, the invention has the advantages of simplicity, convenience and easy operation of a synthesis method of a benzoxazine monomer and a solidification process of poly-benzoxazine without specific equipment requirements and can carry out industrial production in a general plant.

Description

technical field [0001] The present invention relates to a new type of benzoxazine resin—silicon-containing benzoxazine monomer and polymer, as well as its preparation method and application, belonging to the technical field of introducing silicon-modified polybenzoxazine at the molecular level . Background technique [0002] Benzoxazine resin is a newly developed new type of phenolic resin. It is a kind of intermediate containing heterocyclic structure synthesized from phenolic compounds, aldehydes and amine compounds. Under the action of heating and / or catalyst Ring-opening polymerization occurs to form a nitrogen-containing network similar to phenolic resin. Compared with the traditional phenolic resin, the advantage of benzoxazine resin is that it has the heat resistance and flame retardancy of ordinary thermosetting phenolic resin or thermoplastic phenolic resin. At the same time, the resin does not release small molecules during the molding and curing process, and the ...

Claims

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Application Information

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IPC IPC(8): C07F7/18C08G77/452C09D183/10C09D5/00
Inventor 鲁在君张廷廷刘盈高星朱春莉
Owner SHANDONG UNIV
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