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Preparation method of aliphatic diamine with high steric hindrance effect

An aliphatic binary, high steric hindrance technology, which is applied in the fields of special chemicals and fine chemicals, can solve the problems of low purity and high functionality of curing agents, and achieve good yellowing resistance

Pending Publication Date: 2020-11-10
江苏湘园化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The polyvalent secondary amine curing agent prepared by the method disclosed in the above patent can be used in epoxy resin curing occasions that do not require high purity, but when used as a polyurethane (urea) curing agent and chain extender, the purity of the curing agent is not high or Excessive functionality limits applications

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  • Preparation method of aliphatic diamine with high steric hindrance effect
  • Preparation method of aliphatic diamine with high steric hindrance effect
  • Preparation method of aliphatic diamine with high steric hindrance effect

Examples

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Effect test

Embodiment 1

[0025] Embodiment 1: A kind of preparation method of the aliphatic dibasic secondary amine of high steric hindrance effect

[0026] The object of the present invention is to provide an environment-friendly preparation method of linear / branched aliphatic secondary secondary amines with high product yield, high purity, convenient operation, non-toxic and pollution-free low reactivity. The target product can impart good flexibility to the product while significantly reducing the reactivity.

[0027]This secondary amine has two substituted alkyl groups on the α-carbon of the amino group, that is, the substituent on the N atom belongs to the secondary carbon-substituted alkyl group, and the steric hindrance effect is obvious, which effectively reduces the reactivity of the secondary amino group. And can give the product good flexibility. However, the synthesis of aliphatic dibasic secondary amines containing large alkyl substituents on the amino group is difficult.

[0028] The s...

Embodiment 2

[0048] Embodiment 2: A kind of preparation method of the aliphatic secondary amine of high steric hindrance effect

[0049] Add 88.2 g (1.0 mol) of 1,4-butylene diamine, 426.7 g (3.0 mol) of diisobutyl ketone and 0.9 g of platinum carbon catalyst into a stainless steel high-pressure reaction vessel, close the feeding port, and replace the reaction vessel with nitrogen The air was replaced with hydrogen for 3 times and the nitrogen was replaced with hydrogen for 3 times, then the temperature was raised, the temperature was controlled at 60°C, the pressure of hydrogen was not higher than 6.0 MPa, and the reaction was carried out for 10 hours under these conditions, and then the temperature was gradually increased, and the maximum reaction temperature was controlled within 92°C , after a total reaction of 25 hours, the temperature was lowered to 28°C, the hydrogen was vented, and the residual hydrogen was replaced with nitrogen, and the pressure was returned to normal. The reacti...

Embodiment 3

[0051] Embodiment 3: A kind of preparation method of the aliphatic dibasic secondary amine of high steric hindrance effect

[0052] Put 102.8g (1.0 mol) of 1,5-pentanediamine, 274.1g (2.4 mol) of 2,4-dimethyl-3-pentanone and 5g of palladium-carbon catalyst into a stainless steel high-pressure reaction vessel, and replace the reaction with nitrogen Air in container 3 times. Replace the nitrogen with hydrogen for 3 times, raise the temperature, control the hydrogen pressure to 3.0~3.5 MPa, the initial reaction temperature is 60°C, gradually increase the temperature as the reaction progresses, the maximum reaction temperature is controlled within 95°C, after the hydrogenation reaction for 20 hours , lower the temperature, vent the hydrogen, replace the residual hydrogen with nitrogen, and return to normal pressure. The reaction product is filtered, and the filter residue is used as a catalyst for recycling. First distill off excess 2,4-dimethyl-3-pentanone, by-product water and...

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Abstract

The invention discloses a preparation method of aliphatic diamine with a high steric hindrance effect. The method comprises the following steps: by taking aliphatic binary primary amine and ketone asraw materials, reducing an intermediate product diketimine of the aliphatic binary primary amine and the ketone into a binary secondary amine product of which one substituent group of each secondary amino group is a high-steric hindrance alkyl group at the temperature of 40-160 DEG C under the reaction pressure of 0.5-8Mpa in a hydrogen atmosphere by adopting a catalyst. The aliphatic diamine withthe high steric hindrance effect synthesized by the invention has lower reaction activity due to the steric hindrance effect of substituted alkyl on N atoms, and can be used as a slow chain extenderor curing agent of polyurea, polyurethane urea and epoxy resin.

Description

technical field [0001] The invention belongs to the technical field of special chemicals and fine chemicals, and relates to a method for preparing aliphatic secondary secondary amines with high steric hindrance effect. Background technique [0002] Polyurethane / polyurea and epoxy resin have a wide range of applications, and it is impossible for one curing agent to meet all the needs. The development of multi-variety and multi-performance chain extenders is particularly important. [0003] Diamine compounds are chain extenders or curing agents for polyurethane (polyurea) elastomers and epoxy resin materials, and can also be used to synthesize polyamides. Mainly in elastic polyurethane materials (including cast polyurethane elastomers, plastic polyurethane paving materials, polyurethane waterproof coatings, adhesives, sealants, potting adhesives, sprayed polyurethane urea and sprayed polyurea, reaction injection molding polyurethane materials) In the field of non-foaming poly...

Claims

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Application Information

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IPC IPC(8): C07C209/26C07C211/09
CPCC07C209/26C07C211/09
Inventor 周建刘益军王静怡
Owner 江苏湘园化工有限公司
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