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Polyurea compositions from polyaspartic esters and secondary heterocyclic amines derived aspartic esters

A technology of aspartic acid ester and composition, applied in the field of polyurea coating composition, can solve the problems of premature gelation of polyurea coating, application of mixture, etc.

Active Publication Date: 2020-12-18
EVONIK OPERATIONS GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This can lead to premature gelation of polyurea coatings and make it difficult to apply these mixtures to the substrate to be coated

Method used

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  • Polyurea compositions from polyaspartic esters and secondary heterocyclic amines derived aspartic esters
  • Polyurea compositions from polyaspartic esters and secondary heterocyclic amines derived aspartic esters
  • Polyurea compositions from polyaspartic esters and secondary heterocyclic amines derived aspartic esters

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] Example 1. Preparation of a polyaspartate / aspartate mixture from diethyl maleate, 4,4'-diaminodicyclohexylmethane (PACM) and piperidine.

[0068] When equipped with N 2 A 2-liter glass reactor with gas inlet tube, thermocouple and addition funnel was charged with 4,4'-diaminodicyclohexylmethane (PACM) (470.72 g, 2.0 moles) and heated to 80°C. Diethyl maleate (688.8 g, 4 moles) was added slowly while maintaining the temperature at 80-85°C. The mixture was kept at this temperature for 6 hours. An oliquot sample analyzed by gas chromatography showed the presence of 5% by weight (0.32 moles) of diethyl fumarate. Piperidine (27.48 g, 0.32 mol) was added and the mixture was allowed to reach ambient temperature. After 3 days, no diethyl fumarate was detected by gas chromatography.

Embodiment 2

[0069] Example 2. Preparation of a polyaspartate / aspartate mixture from diethyl maleate, 4,4'-diaminodicyclohexylmethane (PACM) and pyrrolidine.

[0070] When equipped with N 2 A 2-liter glass reactor with gas inlet tube, thermocouple and addition funnel was charged with 4,4'-diaminodicyclohexylmethane (PACM) (470.72 g, 2.0 moles) and heated to 80°C. Diethyl maleate (688.8 g, 4 moles) was added slowly while maintaining the temperature at 80-85°C. The mixture was kept at this temperature for 6 hours. A sample analyzed by gas chromatography showed the presence of 5% by weight (0.32 moles) of diethyl fumarate. Pyrrolidine (22.90 g, 0.32 mol) was added and the mixture was allowed to reach ambient temperature. After 3 days, no diethyl fumarate was detected by gas chromatography.

Embodiment 3

[0071] Example 3. Preparation of a polyaspartate / aspartate mixture from diethyl maleate, 4,4'-diaminodicyclohexylmethane (PACM) and piperazine.

[0072] When equipped with N 2 A 2-liter glass reactor with gas inlet tube, thermocouple and addition funnel was charged with 4,4'-diaminodicyclohexylmethane (PACM) (470.72 g, 2.0 moles) and heated to 80°C. Diethyl maleate (688.8 g, 4 moles) was added slowly while maintaining the temperature at 80-85°C. The mixture was kept at this temperature for 6 hours. A sample analyzed by gas chromatography showed the presence of 5% by weight (0.32 moles) of diethyl fumarate. Piperazine (27.69 g, 0.32 mol) was added and the mixture was allowed to reach ambient temperature. After 7 days, no diethyl fumarate was detected by gas chromatography.

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Abstract

The present invention relates to a polyurea coating composition comprising (A) a polyisocyanate; (B) a polyaspartic ester; and (C) an aspartic ester. The polyaspartic ester (B) is represented by the structure (I), where Z = a cycloalkyl, alkyl or aryl group, R1, R2 = alkyl groups containing 1-10 carbon atoms; and n = 2-4. The aspartic ester (C) is derived from a secondary heterocyclic amine in a 3-7 membered ring compound bearing at least one secondary amine functionality. This invention also relates to use of a polyurea coating composition comprising (A)-(C) for the preparation of a polyureacoating. This invention further relates to a process for preparing a polyaspartic / aspartic ester mixture in-situ by initially reacting an ester of fumaric acid or maleic acid with a polyamine and thenreacting the unreacted ester of fumaric acid or maleic acid to completion with a secondary heterocyclic amine. This method makes it possible to prepare a polyurea coating without maleic acid or fumaric acid esters thereby providing a safer and more environmentally friendly product.

Description

Background technique [0001] Polyurea coating compositions having a polyisocyanate binder component and a polyaspartate curing agent for reacting with the polyisocyanate are known in the art. They have been used to make coatings resistant to weathering, abrasion and solvents. Additionally, they can be made rigid and elastic. [0002] EP-A-0,403,921 describes the combination of secondary polyamine-containing polyaspartic esters with lacquer polyisocyanates for the production of coatings without or with a minimal amount of solvent. In EP-A-0,531,249, polyaspartate coating compositions are used in combination with hydroxyl-containing resins, polyaldimines or ketimines as isocyanate-reactive components. [0003] Polyaspartates are usually prepared by reaction of polyamines with dialkyl esters of maleic acid or fumaric acid. If the preparation starts from maleic acid esters, there is a rapid isomerization to fumaric acid esters, which then react with the polyamines to form polyas...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G18/73C09D175/02C08G18/38C12P13/20
CPCC08G18/3821C08G18/73C09D175/02C09D7/40
Inventor G·S·拉尔S·法策尔S·M·博伊斯
Owner EVONIK OPERATIONS GMBH
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