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Preparation method of polymercaptan curing agent

A polythiol and curing agent technology, which is applied in the direction of mercaptan preparation, ether preparation, and alkylene oxide preparation ether, etc. It can solve the problems of difficult reaction, difficulty in obtaining products with high thiol content, and difficult reaction.

Inactive Publication Date: 2018-11-16
SHANDONG EFIRM BIOCHEMISTRY & ENVIRONMENTAL PROTECTION CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, although a general synthetic route for the preparation of polythiol by using thiourea has been theoretically proposed, there are few reports about its detailed preparation process, because in the actual preparation process, the reaction is very difficult, and the reaction is difficult to occur and proceed smoothly. More difficult to obtain high sulfhydryl content products

Method used

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  • Preparation method of polymercaptan curing agent
  • Preparation method of polymercaptan curing agent
  • Preparation method of polymercaptan curing agent

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preparation example Construction

[0034] The invention provides a kind of preparation method of polythiol curing agent, it is characterized in that, comprises the following steps:

[0035] a) under the action of a phase transfer catalyst, reacting chlorinated polyether polyol shown in formula (1) with thiourea in an aqueous solution to obtain an intermediate;

[0036] b) carrying out alkaline hydrolysis reaction of the intermediate and an alkaline substance to generate polythiol shown in formula (2);

[0037]

[0038] Among them, R is selected from and one of

[0039] The degrees of polymerization p, m and n are each independently selected from 0 to 5, and p, m and n are not 0 at the same time;

[0040] The phase transfer catalyst is selected from one or more of quaternary ammonium salt compounds and quaternary phosphonium salt compounds.

[0041] In the preparation method provided by the present invention, the chlorinated polyether polyol shown in formula (1) is reacted with thiourea in water under t...

Embodiment 1

[0073] Add 40.00g (0.159mol hydroxyl) compound of formula 3 (p=1, m=1, n=1, R is 1) and 4.8g boron trifluoride to a 100mL four-necked flask equipped with a thermometer and a stirrer, and start Stir and heat to 70°C, slowly add 19.22g (0.207mol) of epichlorohydrin dropwise at 70°C, and keep warm at 70°C for 1 hour after the dropwise addition, to obtain 59.34g of a light yellow transparent intermediate having the structure of formula 1.

[0074] Continue to add 8.90g of tetrabutylammonium bisulfate and 80% thiourea aqueous solution (containing thiourea 20.26g, 0.269mol) to the system, and stir and react at 70°C for 3h; then add 123.08g of 25% thiourea Sodium carbonate solution (containing 0.290 mol of sodium carbonate), stirred and reacted at 70°C for 2h; cut out the upper oil phase, adjusted the pH value to 5-6 with dilute hydrochloric acid, then washed with 40.00g of 70°C deionized water, and then spun The water was distilled off to obtain a colorless and transparent polythiol...

Embodiment 2

[0077] Add 40.00g (0.159mol hydroxyl) compound of formula 3 (p=1, m=1, n=1, R is 1) and 4.8g boron trifluoride 5H to the 100mL four-neck flask equipped with thermometer and stirrer 2 O, start stirring and heat to 70°C, slowly add 17.74g (0.191mol) of epichlorohydrin dropwise at 70°C, keep warm at 70°C for 1h after the dropwise addition, and obtain a light yellow transparent intermediate with the structure of formula 1 57.86g.

[0078] Continue to add 8.68g tetrabutylammonium bisulfate and 80% thiourea aqueous solution (containing thiourea 18.86g, 0.248mol) to the system, stir and react at 70°C for 3h; then add 113.32g 25% thiourea Sodium carbonate solution (containing 0.267 mol of sodium carbonate), stirred and reacted at 70°C for 2h; cut out the upper oil phase, adjusted the pH value to 5-6 with dilute hydrochloric acid, then washed with 40.00g of 70°C deionized water, and then spun The water was distilled off to obtain a colorless and transparent polythiol.

[0079] Accord...

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Abstract

The invention provides a preparation method of a polymercaptan curing agent. The method comprises the following steps: (a) under the action of a phase transfer catalyst, enabling chloride polyether polyol shown in formula (1) to react with thiourea in a water solution to obtain an intermediate; (b) enabling the intermediate and alkaline matter to be subjected to alkaline hydrolysis reaction to generate polymercaptan shown in formula (2); wherein R is selected from one of groups with formulas shown in the description; polymerization degrees p, m and n are respectively and independently selectedfrom 0-5, and p, m and n cannot be 0 simultaneously; the phase transfer catalyst is selected from one or a plurality of quaternary ammonium salt compounds and quaternary phosphonium salt compounds. The preparation method provided by the invention can be used for successively preparing polymercaptan, the problem that the polymercaptan is difficult to generate through a thiourea leaching process, and the products with high sulfydryl content are obtained and have good product chroma.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a preparation method of a polythiol curing agent. Background technique [0002] After the epoxy resin cross-links with the curing agent, it can be used as a building structural adhesive with excellent performance. It is currently the most widely used adhesive in the field of building structural adhesives. However, the common epoxy resin curing agent is difficult to cure when the temperature is low (<15°C), which limits its application in winter. [0003] At present, one way to solve the problem of low-temperature curing is to modify fatty amines, introduce active groups into fatty amines, and react with epoxy resins to cure at low temperatures; another method is to use mercaptan curing agents. Mercaptan curing agent is a new type of epoxy resin curing agent. Its end group has more than two mercapto groups, which can be used as active groups to cross-link with epoxy ...

Claims

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Application Information

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IPC IPC(8): C07C323/12C07C319/02C07C41/03C07C43/13C07C335/32C08G59/66
CPCC07C41/03C07C319/02C07C335/32C08G59/66C07C43/137C07C323/12
Inventor 邹月马韵升巩智远郭龙龙易先君张建林陈梅梅
Owner SHANDONG EFIRM BIOCHEMISTRY & ENVIRONMENTAL PROTECTION CO LTD
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