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Thermal shrinkage-reversible polyarylamide with dibenzo 8-membered ring (DBCOD) structure containing main chain and preparation method thereof

A technology of polyarylamide and eight-membered ring, which is applied in the field of reversible heat-shrinkable polyarylamide containing dibenzo eight-membered ring structure in the main chain and its preparation field, achieving the effect of simple and feasible synthetic route and correct product structure

Active Publication Date: 2017-09-15
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, so far, no polymers containing a dibenzo eight-membered ring structure in the main chain have been reported, and there is no dibasic acid monomer 5,6,11,12-tetrahydrodi Benzo[a,e][8]annulene-2,8-dicarboxylic acid or 5,6,11,12-tetrahydrodibenzo[a,e][8]annulene-2,9-di The synthesis method of carboxylic acid

Method used

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  • Thermal shrinkage-reversible polyarylamide with dibenzo 8-membered ring (DBCOD) structure containing main chain and preparation method thereof
  • Thermal shrinkage-reversible polyarylamide with dibenzo 8-membered ring (DBCOD) structure containing main chain and preparation method thereof
  • Thermal shrinkage-reversible polyarylamide with dibenzo 8-membered ring (DBCOD) structure containing main chain and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Example 1, 5,6,11,12-tetrahydrodibenzo[a,e][8]annulene-2,9-dicarboxylic acid preparation of

[0034] Step 1: Add methyltriphenylphosphine iodide (21.0g, 52mmol) into a pre-dried 250mL Shrek tube, replace nitrogen three times, then add 40mL ultra-dry tetrahydrofuran through a syringe to form a milky white suspension. At 20°C, add potassium tert-butoxide (5.83g, 52mmol) and continue stirring for 15-30min, then slowly add dibenzocycloheptanone (8.33g, 40.0mmol) through a syringe, and continue stirring at 40°C Reaction 10 ~ 15h. After removing the ylide produced by the reaction through silica gel, 7.67 g of white powder (compound 1) was obtained after column chromatography purification (dichloromethane:n-hexane=1:10), with a yield of 93%. 1 H NMR (400MHz, Acetone-d 5 )δ7.34(d,J=7.0Hz,2H),7.25–7.11(m,6H),5.40(s,2H),3.11(s,4H). 13 C NMR (101MHz, Acetone-d 5 )δ152.44, 141.26, 138.51, 129.15, 128.15, 127.99, 126.43, 116.91, 33.24. MS (ESI) m / z [M-H] + 205.2.

[0035] St...

Embodiment 2

[0039] Example 2, 5,6,11,12-tetrahydrodibenzo[a,e][8]annulene-2,8-dicarboxylic acid preparation of

[0040] Step 1 is the same as Step 1 in Example 1.

[0041] Step 2, add 30mL of anhydrous methanol to a 100mL three-necked reaction flask, heat to 80°C, add silver nitrate (1.43g, 8.4mmol), stir well to dissolve; continue to add iodine (1.07g, 4.2mmol) and compound 1 (814mg, 4mmol), immediately add 30mL of dioxane, keep the temperature under reflux reaction for 24h; distill off the solvent under reduced pressure, add 50mL of dichloromethane and 50mL of water, separate the organic phase, and wash three times with anhydrous sulfuric acid The organic phase was dried over sodium, concentrated under reduced pressure to obtain a yellow oily solid, and purified by column chromatography (dichloromethane: n-hexane = 1:8) to obtain 433 mg of white powder (compound 2), with a yield of 52%. 1 H NMR (400MHz, Acetone-d 5 )δ7.39–6.95(m,6H),4.18(s,2H),3.34(qd,J=8.8,2.2Hz,4H). 13 C NMR (101...

Embodiment 3

[0045] Embodiment 3, the synthesis of polyarylamide A

[0046] Polyarylamide was prepared by Yamazaki-Higashi phosphorylation polycondensation reaction technique. Add 492.6mg (1.5mmol) of 5,6,11,12-tetrahydrodibenzo[a,e][8]annulene-2,9-dicarboxylic acid to a 25mL Shrek tube, 3,4'-di Aminodiphenyl ether 300.3mg (1.5mmol), 1.0mL triphenyl phosphite, 0.6mL pyridine, 300.0mg calcium chloride and 3.0mL ultra-dry N-methyl-2-pyrrolidone (NMP), freeze-thaw and replace nitrogen After three times, it was placed in an oil bath at 120°C for 10 hours. After the reaction liquid was lowered to room temperature, it was slowly poured into 200 mL of methanol to obtain a fibrous precipitate. The product was further washed with methanol and hot water, and dried in vacuum for 24 hours to obtain polyarylamide.

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Abstract

The invention belongs to the technical field of polymer materials and particularly relates to polyarylamide with a dibenzo 8-membered ring (DBCOD) structure containing main chain and a preparation method thereof. The invention also relates to DBCOD-containing diacids: 5, 6, 11, 12-tetrahydro dibenzo [a, e] [8] annulene-2, 8-dicarboxylic acid and 5, 6, 11, 12-tetrahydro dibenzo [a, e] [8] annulene-2, 9-dicarboxylic acid and a preparation method thereof. According to the preparation method of the polyacrylamide, a Yamazaki-Higashi phosphorylation condensation polymerization is adopted and the thermal shrinkage coefficient of the polyarylamide is adjusted through changing the feeding proportion of diacid monomers in the preparation process. The polyacrylamide provided by the invention has excellent solution film forming property and thermal stability and especially unique reversible thermal shrinkage and cold expansion characteristics, which are related to the conformation change of 8-membered rings; and the polyarylamide can serve as a thermal shrinkage material.

Description

technical field [0001] The invention belongs to the technical field of polymer materials, and in particular relates to a polyarylamide whose main chain contains a dibenzo eight-membered ring structure and a preparation method thereof. The invention also relates to a dibasic acid 5 containing a dibenzo eight-membered ring (DBCOD) ,6,11,12-tetrahydrodibenzo[a,e][8]annulene-2,8-dicarboxylic acid and 5,6,11,12-tetrahydrodibenzo[a,e][ 8] Annulene-2,9-dicarboxylic acid and process for its preparation. Background technique [0002] Materials with thermal shrinkage and cold expansion (that is, negative thermal expansion coefficient) can be used to prepare composite materials with zero expansion coefficient that does not change with temperature and whose expansion coefficient can be greatly adjusted due to their abnormal thermal shrinkage properties. At the same time, this type of material can also be used to prepare photosensitive or thermosensitive materials because of its fast ph...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G69/32C08J5/18C07C51/285C07C63/46
CPCC07C1/2076C07C13/547C07C45/00C07C47/546C07C49/675C07C51/285C07C63/46C08G69/32C08J5/18C08J2377/10
Inventor 汪长春王昭
Owner FUDAN UNIV
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