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Rhodamine-based fluorescent indicator for indicating aging degree of rubber and preparation method of indicator

A technology of aging degree and indicator, which is applied in chemical instruments and methods, luminescent materials, organic chemistry, etc., can solve the problems that rubber products cannot be used, aging performance damages detection objects, etc., and achieves low production cost, low price, and simple process Effect

Inactive Publication Date: 2011-08-10
FUJIAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The evaluation of this aging performance often destroys the tested object and cannot be applied to the rubber products in use.

Method used

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  • Rhodamine-based fluorescent indicator for indicating aging degree of rubber and preparation method of indicator
  • Rhodamine-based fluorescent indicator for indicating aging degree of rubber and preparation method of indicator
  • Rhodamine-based fluorescent indicator for indicating aging degree of rubber and preparation method of indicator

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] 1. Preparation of 9,10-dimethyl-2,3-anthracenedicarboxylic anhydride

[0022] Dissolve 8g of 9,10-dimethyl-2,3-anthracenedicarboxylic acid in 200mL of acetic anhydride, and react under reflux for 1 hour. After cooling to room temperature, 3.6 g of 9,10-dimethyl-2,3-anthracene dicarboxylic anhydride was obtained by filtration, with a yield of 60%. 1H NMR (CDCl 3 ): δ: 3.23 (s 6H), 7.72 7.75 (m, 2H), 8.42 8.46 (m, 2H), 9.12 (s, 2H). MS (EI ): m / z 276 (M ). Mp: 278℃ .

[0023]

[0024] 2. Preparation of 9-[2-(3-carboxy-9,10-dimethyl)anthracene]-6-amino-3H-oxanthene-3-imine

[0025] 3g of 9,10-dimethyl-2,3-anthracene dicarboxylic anhydride and 6g of m-aminophenol were dissolved in 60mL of methanesulfonic acid, and reacted at 90°C for 9 hours under the protection of nitrogen. After cooling, the reaction solution was poured into 2000 mL of distilled water, and the precipitate was filtered out and vacuum-dried at 70°C for 20 hours to obtain a red powder. Dissolve this ...

Embodiment 2

[0028] 1. Preparation of 9,10-dimethyl-2,3-anthracenedicarboxylic anhydride

[0029] Dissolve 9g of 9,10-dimethyl-2,3-anthracenedicarboxylic acid in 300mL of acetic anhydride, and react under reflux for 2 hours. After cooling to room temperature, 4.6 g of 9,10-dimethyl-2,3-anthracene dicarboxylic anhydride was obtained by filtration, with a yield of 65%. 1H NMR (CDCl 3 ): δ: 3.23 (s 6H), 7.72 7.75 (m, 2H), 8.42 8.46 (m, 2H), 9.12 (s, 2H). MS (EI ): m / z 276 (M ). Mp: 278℃ .

[0030]

[0031] 2. Preparation of 9-[2-(3-carboxy-9,10-dimethyl)anthracene]-6-amino-3H-oxanthene-3-imine

[0032] 4g of 9,10-dimethyl-2,3-anthracene dicarboxylic anhydride and 8g of NN-diethyl-m-aminophenol were dissolved in 80mL of 98% sulfuric acid, and reacted at 70°C for 12 hours under the protection of nitrogen. After cooling, the reaction solution was poured into 2000 mL of distilled water, and the precipitate was filtered out and vacuum-dried at 65° C. for 24 hours to obtain a red powder. Di...

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Abstract

The invention relates to an indicator for indicating the aging degree of rubber, which is characterized in that: 9,10-dimethyl-2,3-anthracenedicarboxylate is mixed with acetic anhydride to obtain 9,10-dimethyl-2,3-anthracenedimethanoic anhydride by means of reflux reaction; and 9,10-dimethyl-2,3-anthracenedimethanoic anhydride and meta-aminophenol which is twice in weight as much as 9,10-dimethyl-2,3-anthracenedimethanoic anhydride are dissolved in a strongly acidic medium, reaction is performed for 9 to 12 hours at 68 to 90 DEG C, and a 9-[2-(3-carboxyl-9,10-dimethyl)anthracene]-6-amino-3H-xanthene ring-3-imine indicator is obtained by filtration, drying, extraction and benzene recrystallization. The compound prepared according to the method disclosed by the invention can be reacted with singlet oxygen, oxyradical or peroxy radical to generate fluorescent light. The fluorescent light of the indicator gets stronger as the concentration of active oxygen in the rubber increases. By mixing the indicator with various rubbers by certain weight proportions, the aging degree of rubber can be indicated vividly through color change.

Description

technical field [0001] The invention relates to an indicator capable of indicating the aging degree of rubber, in particular to a rhodamine-based fluorescent indicator responsive to active oxygen, which is used for indicating the aging degree caused by automatic catalytic oxidation of rubber. Background technique [0002] During the storage and use of rubber or rubber products, the surface gradually changes color, blooms, becomes sticky and soft, cracks, becomes brittle and hardens, etc. At the same time, the physical and mechanical properties of the rubber decrease, and the strength and elongation decrease sharply. The rate increases, the dielectric properties weaken, so that it loses its use value. These phenomena are called rubber aging. In a variety of use environments, the factors that cause rubber aging are quite complicated. Under the action of different factors, the aging mechanism is also different. Among them, thermal (photo) oxygen aging is the most common and ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/82C09K11/07
Inventor 高勇钱庆荣黄宝铨曹长林许兢陈庆华黄婷
Owner FUJIAN NORMAL UNIV
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