Mannich base as well as preparation method and uses thereof

A technology of Mannich base and dimeric cyclohexanone, which is applied in the field of Mannich base and its preparation, and can solve the problems of color-changing compositions with special importance

Inactive Publication Date: 2008-05-21
YUEYANG CHANGDE CHEM IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are also ketimine crosslinkers based on low molecular weight ketones and amines, but their discoloration during preparation or storage precludes their use in compositions where color is of special importance
[0004] At present, there are reports on aldehyde modification and alcohol modification of dicyclohexanone-based fractions obtained from oil X, but no dicyclohexanone-based fractions have been used to synthesize Mannich The report of base, more do not see the report of this synthesis Mannich base as epoxy resin curing agent

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044]This embodiment is an illustration of the saponification treatment of the dimer raw material of cyclohexanone obtained from the cyclohexanone by-product (commonly known as X oil) used in the present invention. Get dimeric cyclohexanone total content and be 34.4% (w / w) X oil 600g, drop in the 1000ml reactor, start to stir, drip the sodium hydroxide that is configured based on all ketones 3% (w / w) 30% (w / w) aqueous solution, react at room temperature for 30 minutes, then add an appropriate amount of sulfuric acid to neutralize the pH of the reaction solution to 7-8, and then stop stirring. After phase separation, the lower saline phase was separated off. Then wash with water twice, and under negative pressure of 960KPa, distill and collect fractions at 150° C. to 220° C. to obtain 234.5 g of dicyclohexanone (content: 80.1%), with a yield of 91.1%.

Embodiment 2

[0046] Get 100.0 g of dicyclohexanone with a total ketone content of 80.1% (w / w) prepared in Example 1, and put it into a 250 ml reactor. Ventilate nitrogen and start stirring. Add 26.7g of ethylenediamine dropwise at room temperature. After the addition, continue to slowly add 13.3g of paraformaldehyde solid. The addition is completed within 60 minutes. The temperature of the addition process is controlled at 60°C. After the addition was complete, the reaction was carried out at room temperature for 8 h. The product was obtained by removing 7.9 g of water from the reaction material under a negative pressure of 990 Kpa, with a yield of 95.0%.

Embodiment 3

[0048] Get 100.0 g of dicyclohexanone with a total ketone content of 80.1% (w / w) prepared in Example 1, and put it into a 250 ml reactor. Nitrogen was blown and stirring was started, and 50.7g of 1,2-diaminocyclohexane was added at room temperature, and 44.3g of 30% formaldehyde aqueous solution was added dropwise after the addition was completed, and the addition was completed within 60 minutes. The temperature of the addition process was controlled at 60°C. After the addition was complete, the temperature was raised to 80° C. for 2 h. Remove 39.0 g of water from the reaction material under a negative pressure of 990 Kpa to obtain the product with a yield of 94.7%.

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Abstract

The present invention relates to a mannich base which is synthesized by the mannich reaction of dimeric cyclohexanone and formaldehyde with at least one kind of polyamine, wherein, the dimeric cyclohexanone is the dimer of the cyclohexanone, comprising the single or mixed form of 2-(1-cyclohexenyl) cyclohexanone, 2-(1-cyclohexyl) cyclohexanone and 2-(1-cyclohexylidene) cyclohexanone. The concrete preparation method of the product of the present invention is characterized in that by-product containing dimeric cyclohexanone autoclave liquid during the process of the cyclohexanone production is processed for the saponification treatment to collect the dimeric cyclohexanone by distilling (or obtain the dimeric cyclohexanone product directly), the dimeric cyclohexanone and the formaldehyde react with at least one kind of the polyamine for one to ten hours under 10 DEG C to 100 DEG C to be dehydrated to obtain the product. The product of the present invention is mainly used as curing agent to be applied in an epoxy system or a polyurethane system.

Description

technical field [0001] The invention relates to a Mannich base and its preparation method and application. Background technique [0002] 2-(1-cyclohexenyl)cyclohexanone is a dimer of condensation and dehydration of cyclohexanone, with a boiling range of 150°C to 180°C at a pressure of 400Pa. In industry, the direct condensation of cyclohexanone is generally used to produce 2(1-cyclohexenyl)cyclohexanone. In addition, it can also be recovered from the by-product still liquid (commonly known as X oil) in the production process of cyclohexanone - when cyclohexane liquid-phase air oxidation produces cyclohexanol / cyclohexanone mixture, the column still in the product rectification process The heavy components in the product account for 5% to 10% of the output of cyclohexanol / cyclohexanone, mainly various condensation products of cyclohexanone, and mainly dicyclohexanone. [0003] Mannich bases are well known to professionals as curing agents for epoxy resins and polyurethanes. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C225/12C07C225/14C08K11/00
Inventor 黄金城高林辉何双林屈铠甲何嘉勇
Owner YUEYANG CHANGDE CHEM IND
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