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Triazole ring and ether bond-containing maleimide, and preparation method and use of resin thereof

A technology of maleimide and triazole ring, which is applied in the field of preparation of maleimide and its resin, can solve the problems of poor solubility and high melting point, achieve high glass transition temperature and decomposition temperature, good toughness, Effect of excellent machinability characteristics

Inactive Publication Date: 2013-04-24
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] M.Save [M.Sava, Journal of Applied Polymer Science, 2006, 101, 567] synthesized a series of maleimides whose main chain contains amide bonds, but their solubility is poor, and they can only be dissolved in DMF at room temperature And NMP, the melting point is also higher ((a) 324 ~ 327 ° C, (b) 232 ~ 236 ° C, (c) 237 ~ 240 ° C, (d) 102 ~ 107 ° C), its performance has a lot to do with the main chain structure relation

Method used

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  • Triazole ring and ether bond-containing maleimide, and preparation method and use of resin thereof
  • Triazole ring and ether bond-containing maleimide, and preparation method and use of resin thereof
  • Triazole ring and ether bond-containing maleimide, and preparation method and use of resin thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Synthesis of TA-BMI

[0031] 1.88g (0.01mol) 1,4-diazidemethylbenzene, 4.99g (0.022mol) propargyloxyphenylmaleimide, 0.25g (0.001mol) CuSO 4 ·5H 2 0, 0.40g (0.002mol) sodium ascorbate and 15mLDMF add 100mL one-necked flask, under magnetic stirring, room temperature reaction 48h; After reaction finishes, reactant is poured into the deionized water precipitation of 1600mL, and suction filtration separates the solid initial product; The initial product was washed with 15 mL of acetone and dried to obtain a light yellow TA-BMI solid with a yield of 98%. FT-IR (KBr, cm -1 ), 3130 (-H, triazole ring), 3097 (=C-H, imide ring), 1712 (C=O), 1251, 1051 (Ar-O-), 1149 (C-N-C), 836 (C=C , imide ring). 1 H NMR (DMSO, TMS) δ [subscript indicates structural position]: 7.15(d, 4H, H a ), 7.33 (d, 4H, H b ), 7.10 (d, 4H, Hc ), 5.15(s, 4H, H d ), 8.30(s, 2H, H e ), 5.60(s, 4H, H f ), 7.22(d, 4H, H g ), its structural formula is:

[0032]

[0033] TA-BMI is soluble in strong ...

Embodiment 2

[0035] Synthesis of TA2-BMI

[0036] 2.64g (0.01mol) 4,4'-diazidemethylbiphenyl, 4.99g (0.022mol) propargyloxyphenylmaleimide, 0.25g (0.001mol) CuSO 4 ·5H 2 0, 0.40g (0.002mol) sodium ascorbate and 20mL DMF add 100mL one-necked flask, under magnetic stirring, room temperature reaction 48h; After reaction finishes, reactant is poured into the deionized water precipitation of 1800mL, and suction filtration separates solid initial product; The initial product was washed with 20 mL of acetone and dried to obtain a light yellow TA2-BMI solid with a yield of 96%. FT-IR (KBr, cm -1 ), 3141 (-H, triazole ring), 3099 (=C-H, imide ring), 1711 (C=O), 1246, 1050 (Ar-O-), 1151 (C-N-C), 830 (C=C , imide ring). 1 H NMR (DMSO, TMS) δ [subscript indicates structural position]: 7.15(d, 4H, H a ), 7.23(d, 4H, H b ), 7.11 (d, 4H, H c ), 5.19 (s, 4H, H d ), 8.36(s, 2H, H e ), 5.67(s, 4H, H f ), 7.41(d, 4H, H g ), 7.68 (d, 4H, H h ), its structural formula is:

[0037]

[0038] TA2-...

Embodiment 3

[0040] Synthesis of TA3-TMI

[0041] 2.85g (0.01mol) 1,3,5-trimethyl-2,4,6-triazidemethylbenzene, 7.49g (0.033mol) propargyloxyphenylmaleimide, 0.375g (0.0015mol)CuSO 4 ·5H 2 O, 0.59g (0.003mol) sodium ascorbate and 25mL DMF were added to a 100mL single-necked flask, and under magnetic stirring, the room temperature was reacted for 48h; after the reaction was completed, the reactant was poured into 2000mL of deionized water for precipitation, and the solid primary product was isolated by suction filtration; The initial product was washed with 25 mL of acetone and dried to obtain light yellow TA3-TMI solid with a yield of 93%. FT-IR (KBr, cm -1 ), 3139 (-H, triazole ring), 3099 (=C-H, imide ring), 1713 (C=O), 1244, 1047 (Ar-O-), 1149 (C-N-C), 831 (C=C , imide ring), 1397 (-CH 3 ). 1 H NMR (DMSO, TMS) δ [subscript indicates structural position]: 7.21(d, 6H, H a ), 7.11(d, 12H, H b ), 5.12(s, 6H, H d ), 8.11(s, 3H, H e ), 5.71(s, 6H, H f ), 2.40(s, 9H, H i ), its stru...

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Abstract

The invention relates to triazole ring and ether bond-containing maleimide, and a preparation method and use of resin thereof. Triazole ring and ether bond-containing polymaleimide is synthesized by performing 1,3-dipolar cycloaddition reaction on raw materials consisting of propargyloxy phenyl maleimide and trinitrides; and the novel maleimide resin is prepared by modifying the maleimide by adopting diallyl bisphenol A. The invention has the advantages that: the prepared modified maleimide resin has high processability and high resistance to high temperature; and the maleimide and the modified resin thereof can be applied as resin substrates of electric appliance insulating materials, wear-resistant materials, aerospace structural materials and the like.

Description

【Technical field】 [0001] The invention relates to the technical field of functional resins, in particular to a preparation method and application of a maleimide containing a triazole ring and an ether bond and a resin thereof. 【Background technique】 [0002] Bismaleimide (BMI) is a bifunctional thermosetting resin with maleimide as the active terminal group. BMI resin has excellent properties such as high temperature resistance, radiation resistance, heat and humidity resistance, high modulus and small thermal expansion coefficient. For this reason, countries attach great importance to the research, development and application of BMI resins. So far, a series of BMI resins with excellent performance have been developed and widely used in aviation, aerospace and electronic and electrical fields. In 1948, American Searle obtained the synthesis patent of BMI [US.2444536, 1948]. Since then, people have improved the Searle synthesis method and synthesized various BMI monomers wi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D403/14C08F222/40C08F212/34C08L35/06C08L25/18
Inventor 杜磊黄发荣王晓飞万里强扈艳红
Owner EAST CHINA UNIV OF SCI & TECH