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Fluorescent aliphatic polyamide imide as well as preparation method and application thereof

A polyamide-imide and aliphatic technology, which is applied in the field of fluorescent aliphatic polyamide-imide and its preparation, can solve the problems of no report on fluorescent aliphatic polyamide-imide, difficult processing and molding of aromatic PAI, etc. , to achieve the effects of wide application range, short reaction time and low preparation cost

Active Publication Date: 2016-08-24
JIANGSU INST OF NUCLEAR MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Chinese patent document CN102241822A discloses an aliphatic polyamide-imide, which has good solubility and can be completely dissolved after being heated to 60°C in organic solvents NMP, DMF, DMAc or DMSO, with a solubility of >6g / 100mL, which overcomes the The inadequacies of poor solubility and difficult processing and molding of aromatic PAI
[0004] There is no report of fluorescent aliphatic polyamide-imide so far

Method used

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  • Fluorescent aliphatic polyamide imide as well as preparation method and application thereof
  • Fluorescent aliphatic polyamide imide as well as preparation method and application thereof
  • Fluorescent aliphatic polyamide imide as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Example 1 Synthesis of Intermediate Thiolactone-Maleimide Monomer (Ⅱ)

[0057]

[0058] (1) Synthesis of 2-bromo-2-methyl-nitrogen-(2-oxotetrahydrothiophen-3-yl)propionamide (c)

[0059]

[0060] Homocysteine ​​thiolactone (7.10g, 46.3mmol) and triethylamine (11.2g, 110.9mmol) were dissolved in 150mL of chloroform, placed in an ice bath, and argon flowed. 2-Bromoisobutyryl bromide (12.65 g, 55.5 mmol) was slowly dropped into the reaction solution, and stirred overnight at room temperature. After the reaction, the reaction solution was diluted with dichloromethane (150 mL), filtered and washed with water (60 mL*3). Combined organic phases, anhydrous MgSO 4 After drying and filtering, a light yellow oily liquid was obtained. After column chromatography (ethyl acetate / n-hexane=1:2), white crystals were obtained. Yield: 49.7%.

[0061] The structural confirmation data is as follows: 1 HNMR (300MHz, CDCl 3 , ppm) δ7.04(s, 1H), 4.45(dt, J=13.0Hz, J=6.5Hz, 1H), 3....

Embodiment 2

[0074] Example 2 Synthesis of Fluorescent Aliphatic Polyamide-imide PAI1

[0075]

[0076] Polycondensation reaction: thiolactone-maleimide monomer (36.3mg, 0.1mmol) was dissolved in 1mL DMSO, argon flowed, then 1,3-propylenediamine (7.4mg, 0.1mmol) was added, stirred at room temperature , dynamic NMR tracking. After the reaction, the reaction solution was precipitated in acetone and dried in vacuum for 3 hours.

[0077] The equivalent reaction of thiolactone-maleimide and 1,3-propanediamine does not need to add a base as a catalyst. 1,3-Propanediamine will undergo ring-opening reaction with thiolactone and Michael addition reaction with maleimide at the same time. We followed the reaction with NMR, and the experimental results are shown in Figure 1(a) and Figure 1(b).

[0078] By Fig. 1 (a) and Fig. 1 (b) as can be seen, the double bond proton signal peak (δ=7.08ppm, h) of maleimide and the methine proton signal peak of homocysteine ​​thiolactone (δ=7.08ppm, h) gradu...

Embodiment 3

[0081] Example 3 Synthesis of Fluorescent Aliphatic Polyamide-imide PAI2

[0082]

[0083] Polycondensation reaction: thiolactone-maleimide monomer (36.3mg, 0.1mmol) was dissolved in 1mL DMSO, and argon was added, then 2,2-dimethyl-1,3-propylenediamine (0.1 mmol), stirring at room temperature, and dynamic NMR tracking. After the reaction, the reaction solution was precipitated in acetone and dried in vacuum for 3 hours.

[0084] Structure confirmation data such as image 3 shown.

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Abstract

The invention relates to fluorescent aliphatic polyamide imide as well as a preparation method and application thereof. The fluorescent aliphatic polyamide imide is of a structure as shown in a formula (I) (described in the specification) and has fluorescence in a solvent and when in solid state respectively, solid fluorescence and solution fluorescence are obviously different, and in the solvent, fluorescence intensity is reduced along with enhancement of solvent polarity; meanwhile, sulfydryl contained in a side chain is beneficial to subsequent modification of polyamide imide.

Description

technical field [0001] The invention belongs to the field of polymer chemistry, and in particular relates to a fluorescent aliphatic polyamide-imide and its preparation method and application. Background technique [0002] Polyamide-imide is a class of advanced engineering materials that combines the excellent mechanical strength, thermal stability and flexibility of polyamide and polyimide. Recently, polyamideimides have received much attention as membrane materials, gel electrolytes for solar cells, and fluorescent polymers. Generally speaking, polyamide-imides are non-fluorescent, and only aromatic or semi-aromatic polyamide-imides modified with fluorescent moieties have fluorescence. Professor Endo proposed the basic principle of designing strong fluorescent polyimides: cycloaliphatic diamines and aromatic dianhydrides containing flexible units must be used. In contrast, aliphatic polyamides exhibit neither absorption nor fluorescence due to the forbidden transition an...

Claims

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Application Information

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IPC IPC(8): C08G73/14C09K11/06C07D409/14
CPCC07D409/14C08G73/14C09K11/06C09K2211/1466
Inventor 严骏杰杨敏潘栋辉徐宇平杨润琳王立振赵富宽张波
Owner JIANGSU INST OF NUCLEAR MEDICINE
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