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Ester-group-containing diamine type fluorenyl benzoxazine

A technology of ester-based diamine type and fluorenylbenzene, which is applied in the field of organic polymer materials, can solve the problems of limited application and high brittleness of polybenzoxazine resin, and achieve the effects of shortening reaction time, improving toughness and processing performance

Inactive Publication Date: 2012-10-03
HARBIN ENG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the pendant fluorenyl groups in the existing fluorenyl benzoxazine resins, the polybenzoxazine resins are more brittle, which limits the further application of such resins

Method used

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  • Ester-group-containing diamine type fluorenyl benzoxazine
  • Ester-group-containing diamine type fluorenyl benzoxazine
  • Ester-group-containing diamine type fluorenyl benzoxazine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Add 4.64g (0.01mol) 9,9-bis(4-aminobenzoic acid methyl) fluorene, 1.9g (0.02mol) phenol, 1.2 g (0.04mol) paraformaldehyde and 60mL xylene. Heat to 150°C and reflux for 6 hours. After the reaction, cool to room temperature, add ethanol, wash the precipitate several times, filter, and vacuum dry to obtain white powder 9,9-bis(4-aminobenzoic acid methyl)fluorene - Phenylbenzoxazine monomer (BAPMFp), yield 72.3%.

[0026] H NMR test results (500M, CDCl 3 , ppm): 6.61~7.92 (m, 24H, Ar-H), 5.40 (d, 4H, O-CH 2 -N), 4.71 (d, 4H, Ar-CH 2 -N), 4.66 (d, 4H, O-CH 2 -C); infrared spectrum test results (KBr, cm □1 ):2888 (stretching vibration of methylene), 1708 (stretching vibration of ester carbonyl), 1606 and 1455 (skeleton vibration of benzene ring), 1322 (swinging vibration of methylene on oxazine ring), 1101 and 1227 (C-O-C symmetry and asymmetric stretching vibration), 1182 (C-N-C symmetric and asymmetric stretching vibration), 954 (C-H out-of-plane bending vibration of ...

Embodiment 2

[0029] Except that the raw material phenol was changed to m-cresol, and the mass was 2.16g, other conditions were the same as in Example 1, and finally light yellow 9,9-bis(4-aminobenzoic acid methyl)fluorene-m-cresolyl benzoxazine was obtained Monomer (BAPMF-m-mp), yield 67.8%.

[0030] H NMR test results (500M, CDCl 3 , ppm): 6.65~7.93 (m, 22H, Ar-H), 5.42 (d, 4H, O-CH 2-N), 4.74 (d, 4H, Ar-CH 2 -N), 4.66 (d, 4H, O-CH2-C), 2.26 (d, 6H, -CH 3 ); infrared spectrum test results (KBr, cm -1 ): 2884, 1709, 1607, 1455, 1325, 1227, 1101, 1183 and 956.

[0031] Curing and testing conditions are the same as in Example 1, polybenzoxazine resin (poly(BAPMF-m-mp)), T g : 166,T 5 :379,Y C : 33%.

Embodiment 3

[0033] Except that the raw material phenol is used instead of p-cresol, and the reaction time is 15h, other conditions are the same as in Example 2, and finally obtain light yellow 9,9-bis(4-aminobenzoic acid methyl) fluorene-p-phenol benzoxazine mono body (BAPMF-p-mp), the yield was 61.2%.

[0034] H NMR test results (500M, CDCl 3 , ppm): 6.65~7.93 (m, 22H, Ar-H), 5.42 (d, 4H, O-CH 2 -N), 4.74 (d, 4H, Ar-CH 2 -N), 4.67 (d, 4H, O―CH2―C), 2.24 (d, 6H, -CH 3 ); infrared spectrum test results (KBr, cm -1 ): 2897, 1708, 1609, 1455, 1323, 1226, 1099, 1182 and 954.

[0035] Curing and testing conditions are the same as in Example 1, polybenzoxazine resin (poly(BAPMF-p-mp)), T g : 155,T 5 : 355, Y C : 31%.

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Abstract

The invention provides an ester-group-containing diamine type fluorenyl benzoxazine, which comprises the following structure shown as the accompanying drawing, in the formula, A is fluorenyl containing C1 to C4 alkyl groups, fluorenyl containing substituted or unsubstituted aromatic ring or fluorenyl containing phenoxy ethyl, and R1 is one kind of materials from hydrogen, methyl, methoxy group, trifluoromethyl or cyanogroup. The ester-group-containing fluorenyl diamine monomers are used as amine resources for synthesizing the ester-group-containing diamine type fluorenyl benzoxazine. Flexible ester groups are introduced in the benzoxazine monomer molecular structure for improving the toughness and the processing performance of the benzoxazine. The ester-group-containing diamine type fluorenyl benzoxazine prepared by a method provided by the invention can be used in the fields of advanced composite material base resin, electronic encapsulating materials, insulation materials, laminated materials and the like.

Description

technical field [0001] The invention relates to an organic polymer material, in particular to an ester group-containing diamine type fluorenyl benzoxazine monomer. Background technique [0002] In the 1970s, Schreiber first reported the use of benzoxazine oligomers to modify epoxy resins in patents (German patent 2217099, "Phenolic resin as electric insulator"). In the 1980s, Higginbottom first discovered the crosslinking reaction of multifunctional benzoxazines in the research of coating materials (US Patent 4501864, "Polymerizable compositions comprising polyamines and poly(dihydrobenzoxazines)"). In 1994, Ishida and Ning first completed the performance research on polybenzoxazines (Ning X, Ishida H. Phenolic materials via ring-opening polymerization-synthesis and characterization of bisphenol-A based benzoxazines and their polymers.J Polym Sci A Polym Chem, 1994, 32:1121-1129P). A large number of studies have found that benzoxazine resin is a new type of resin material ...

Claims

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Application Information

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IPC IPC(8): C07D265/16C08G73/06
Inventor 刘文彬何轩宇王军李新张庆伟
Owner HARBIN ENG UNIV
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