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Crosslinkers based on dibenzalacetone derivatives

A technology of amidophenyl and methoxyformylphenyl, which is applied in the field of cross-linking agents based on dibenzylideneacetone derivatives, and can solve the problem of high cost

Inactive Publication Date: 2002-01-09
EASTMAN CHEM CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This trifunctional amine is very expensive for most applicators used in coatings

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment Embodiment 1

[0020] Examples Example 1: 1,5-bis-(4'-methoxyformylphenyl)-1,4-pentadien-3-one (1)

[0021] 1,5-Bis-(4'-methoxyformylphenyl)-1,4-pentadien-3-one 1 was obtained by the method described in US Patent 5,025,086. Example 2: 1,5-bis-(4'-methoxyformylphenyl)-3-pentanone (2)

Embodiment 2

[0021] 1,5-Bis-(4'-methoxyformylphenyl)-1,4-pentadien-3-one 1 was obtained by the method described in US Patent 5,025,086. Example 2: 1,5-bis-(4'-methoxyformylphenyl)-3-pentanone (2)

[0022] Procedures for obtaining this material are described earlier in US Patent 4,965,399 employing a wide range of hydrogenation conditions. The materials used throughout the application were prepared as follows.

[0023] 1,5-bis-(4'-methoxyformylphenyl)-1,4-pentadien-3-one (52.56 g, 0.15 mol), 5% palladium on carbon (3.0 g) and THF (800 mL). The air was evacuated and the flask was filled with hydrogen in two helium balloons (about 4 liters each). The emptying step of each balloon was repeated three times, and the mixture was stirred rapidly at room temperature (approximately 25°C). After stirring overnight, a sample was removed, filtered through filter aid and detected by FDMS. Over 24 hours, the entire mixture was filtered through a Dicalite(R) filter aid (available from Aldrich Chemica...

Embodiment 3

[0023] 1,5-bis-(4'-methoxyformylphenyl)-1,4-pentadien-3-one (52.56 g, 0.15 mol), 5% palladium on carbon (3.0 g) and THF (800 mL). The air was evacuated and the flask was filled with hydrogen in two helium balloons (about 4 liters each). The emptying step of each balloon was repeated three times, and the mixture was stirred rapidly at room temperature (approximately 25°C). After stirring overnight, a sample was removed, filtered through filter aid and detected by FDMS. Over 24 hours, the entire mixture was filtered through a Dicalite(R) filter aid (available from Aldrich Chemical Company) in a fritted glass funnel, washed with THF and concentrated in vacuo to yield a quantity of white solid. Example 3: 1.5-bis-(4'-amidophenyl)-3-iminopentane (3)

[0024] Route 1: Suspension (300 mL) of 1,5-bis-(4'-methoxyformylphenyl)-3-pentanone (5.40 g, 15.2 mmol) in concentrated ammonia water at room temperature (about 25 °C) under rapid stirring for four days. Some of the suspension ad...

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PUM

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Abstract

The present invention relates to the composition, process of preparation, and use of novel derivatives prepared from 1,5-bis-(4'-carbomethoxyphenyl)-1,4-pentadien-3-one. These novel compositions can act as crosslinkers with polyfunctional monomeric, oligomeric, and / or polymeric anhydrides, esters, carboxylic acids, isocyantes, epoxies, carbonates, acetoacetates, and alkoxylated melamines.

Description

Background of the invention [0001] Dibenzylideneacetone derivatives are generally prepared by reacting two moles of benzaldehyde derivatives with one mole of acetone, usually under basic conditions. Aldol reactions of this type are known and have been specifically described by Blount and Zoeller in U.S. Pat. Formylphenyl)-1,4-pentadien-3-one. [0002] Hydrogenation of the dibenzylideneacetone backbone (pentadienone units) with a homogeneous or heterogeneous catalyst gives a 3-pentanone or 3-pentanol structure, which is particularly advantageous for the development of coatings, especially cross-linked Multifunctional derivatives of coupling agents. Only Blount and Zoeller in U.S. Patent 5,025,086 describe a hydrogenation process for the preparation of cycloaliphatic derivatives of dibenzylideneacetone, more specifically 1,5-bis-(4'-methoxycarbonylcyclohexyl)-3 -pentanol and 1,5-bis-(4'-methoxycarbonylcyclohexyl)-3-pentanone. [0003] In the cited references, the use of dibe...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C29/149C07B61/00C07C31/27C07C209/70C07C211/18C07C211/27C07C231/12C07C237/24C07C237/32C09D201/02
CPCC09D201/02C07C237/24C07C211/27C07C2101/14C07C211/18C07C31/27C07C237/32C07C2601/14
Inventor P·C·黑德特M·L·埃利奥特
Owner EASTMAN CHEM CO
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