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Indandione compounds and its preparing process and application

A technology of indanedione and indanedihydroxydiketone, which is applied in the field of indanedione compounds, can solve the problems of low reliability, complicated preparation method, high production cost, etc., and achieve high reliability, simple detection method, Effects that are not easy to imitate

Inactive Publication Date: 2002-10-30
TIANJIN GUARD T & D
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] However, the above-mentioned patents have never pointed out and verified that the disclosed compound has both photomagnetic and photochromic functions
If a material with only a single function is used in anti-counterfeiting technology, it is easier to be copied, so its reliability is low
Moreover, the preparation methods of the compounds disclosed in the above-mentioned patents are comparatively complicated. Starting from the synthesis of binindrone, Grignard reagent addition, high-temperature dehydration, Zn / ZnCl 2 Reduction, a total of four steps, the production cost is relatively high

Method used

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  • Indandione compounds and its preparing process and application
  • Indandione compounds and its preparing process and application
  • Indandione compounds and its preparing process and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] 3,3'-Diethyl-3,3'-dihydroxy-2,2'-diindan-1,1'-dione

[0029] The first step: the synthesis of 2,2'-diindan-1,1',3,3'-tetraketone Add 25.0 grams of phthalic anhydride and 20.0 grams of succinic acid into a 500-milliliter four-necked flask equipped with a thermometer, a reflux condenser and mechanical stirring, and stir and heat until the solids are completely melted. When all the solids are melted, add 6.0 g of anhydrous potassium acetate, react at 210°C for 2 hours, after cooling, add hot water to boil for 2 hours, and filter. The resulting precipitate was dissolved in methanol, and 50 ml of 2 mol / l sodium methoxide solution was rapidly added dropwise under stirring, and the reaction was refluxed for 0.5 hour, cooled, and filtered. The resulting precipitate was boiled with distilled water for 1 hour and filtered. The filtrate was neutralized to acidity with 1mol / l hydrochloric acid solution, and a purple-red precipitate was precipitated. The purple-red precipitate w...

Embodiment 2

[0036] 3,3'-Dipropyl-3,3'-dihydroxy-2,2'-diindan-1,1'-dione

[0037] The first step: the synthesis of 2,2'-diindan-1,1',3,3'-tetraketone

[0038] The synthesis steps are the same as in Example 1.

[0039] Step 2: Synthesis of Bifunctional Photomagnetic Chromogenic Compounds

[0040] Add 24.0 g of 2,2'-diindan-1,1',3,3'-tetraketone and 500 ml of benzene After the addition, react at room temperature for 12 hours under the protection of nitrogen, and continue to stir for a period of time. After the reaction is completed, it is hydrolyzed with saturated ammonium chloride solution and left standing, and a yellow precipitate insoluble in the two phases is precipitated. The precipitate was purified by column chromatography and recrystallized with dichloromethane to obtain yellow bifunctional photomagnetic color crystal 3,3'-dipropyl-3,3'-dihydroxy-2,2'-biindane-1 , 1'-diketone 14.3 g, yield: 45.5%. The single crystal structure of the compound is as Figure 4 shown.

[0...

Embodiment 3

[0044] 3,3'-Diphenyl-3,3'-dihydroxy-2,2'-diindan-1,1'-dione

[0045] The first step: the synthesis of 2,2'-diindan-1,1',3,3'-tetraketone

[0046] Mix 20 grams of nindanhydrin with 600 milliliters of sulfuric acid solution, which is prepared from 300 milliliters of concentrated sulfuric acid and 300 milliliters of water, and react for 30 minutes under back distillation. A dark purple solid precipitated out and was filtered. Dissolve the solid with 600 ml of glacial acetic acid, boil for half an hour, cool, pour this solution into a 2000 ml ice-water bath, and precipitate a dark reddish-brown solid. Wash the dark reddish-brown solid with water to remove residual acid solution, dry it, and recrystallize it in toluene to obtain 9.3 g of dark purple-brown needle-like crystals of 2,2'-bisindane-1,1',3,3'-tetraketone , Yield: 57.1%. Melting point: 280-282°C.

[0047] Step 2: Synthesis of Bifunctional Photomagnetic Chromogenic Compounds

[0048] In the ether solution of pheny...

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Abstract

A novel indandione compound is disclosed, which is the indandihydroxydione and is prepared by simple two-step process. Said compound is an unsaturated one using the keto containing 6-section ring as the part of its ring and the can be as photomagnetic and photochromic material used in antiforge field.

Description

technical field [0001] The technical solution claimed in the present invention relates to an unsaturated compound containing a six-membered ring ketone group as a component of the ring, that is, an indandione compound, and a preparation method of such compounds and as a photoinduced magnetic and photoinduced Application of color-changing materials. Background technique [0002] In the research of special materials such as photochromism and photomagnetism, indanediones have attracted people's attention. JP0436257 describes indanediones having the following structural formula. It is pointed out in the article that these compounds have photochromic properties. [0003] JP04 180604 introduces indanediones having the following structural formula. It is pointed out in the article that this kind of compound has photomagnetic properties, and is used as an organic magnetic material that can generate magnetism after being illuminated. [0004] However, the above-mentioned patent...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/747C07D207/333C07D263/32C07D333/22C09D5/16C09D11/12C09D11/50
Inventor 孟继本李明智徐黎立董轶望王辉初春李平雷涛李永刚谢伟
Owner TIANJIN GUARD T & D
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