Polyesteramine Synthesis via Segmented Esterification
Find Innovative SolutionsGenerate Solutions
Solution Overview
Problem
There is a need for new cationic oligomeric or polymer compounds with improved properties such as ease of preparation, stability, reduced synthesis cost, enhanced toxicity and biodegradability, and improved technical performance for applications in industries like hygiene, cosmetics, and oil and gas, which current fatty alkylamines and quaternary ammonium derivatives do not adequately meet.
Innovation Solution
The development of a family of polyesteramines and polyesterquats obtained through the condensation of alkoxylated fatty amines with dicarboxylic acids and alkanolamines, followed by potential quaternization, offering improved properties and versatility in applications.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If new cationic oligomeric or polymer compounds are developed to improve technical performance and environmental properties, then effectiveness and biodegradability are improved, but synthesis complexity and cost increase
Solution Approach 1:
The synthesis is divided into two independent stages: first forming polyesteramine intermediates from alkoxylated fatty amines and dicarboxylic acids, then quaternizing with alkyl halides. This segmentation allows each stage to be optimized separately and simplifies process control while achieving complex molecular structures with improved effectiveness and biodegradability.
Solution Approach 2:
The polyesteramine intermediates are prepared in advance through condensation reactions before the final quaternization step. This preliminary action enables better control over molecular weight and structure, ensuring improved technical performance while maintaining manageable synthesis complexity through staged preparation.
2Reliability
If polymeric or oligomeric structures with higher molecular weights are used to improve effectiveness, then technical performance is improved, but ease of manufacture decreases
Solution Approach 1:
The molecular weight and degree of polymerization are controlled by adjusting the molar ratios of reactants (alkoxylated fatty amine to dicarboxylic acid) and controlling reaction conditions such as temperature and time. This allows optimization of effectiveness while maintaining ease of manufacture through parameter adjustment rather than complex process changes.
Solution Approach 2:
The manufacturing process is segmented into distinct condensation and quaternization stages, each with controlled duration and conditions. This segmentation makes the production of high molecular weight compounds more manageable by breaking down the overall process into controllable steps, improving ease of manufacture while achieving desired effectiveness.
3Ease of manufacture
If conventional fatty alkylamines are used, then ease of preparation is maintained, but environmental properties and biodegradability are insufficient
Solution Approach 1:
The invention creates composite molecular structures combining alkoxylated fatty amine chains with dicarboxylic acid backbones and quaternary ammonium groups. This composite structure maintains the ease of preparation from readily available starting materials while incorporating biodegradable ester linkages and reduced toxicity through the specific molecular architecture, thus improving environmental properties without sacrificing manufacturing simplicity.
Solution Approach 2:
The chemical structure is modified by introducing biodegradable ester bonds through dicarboxylic acid incorporation and controlling the alkoxyl chain length and composition. These parameter changes improve biodegradability and reduce toxicity while maintaining ease of preparation from commercially available alkoxylated fatty amines and dicarboxylic acids.
Applied Scientific Principles
This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.
Function Achieved in This Case
The resulting compounds demonstrate ease of preparation, stability, and enhanced performance as surfactants, corrosion inhibitors, and in various industrial applications, with improved adsorption, viscosifying, and emulsifying properties, making them suitable for diverse industrial uses.
Implementation Method 1
condensation by esterification of: A/ at least one alkoxylated fatty amine of formula (I), or of the partial or total quaternization product of said alkoxylated fatty amine
Implementation Method 2
one or more of the nitrogen atoms is (are) quaternized by reaction with a reagent of formula R5
Data Source
AI summary
The present invention relates to compounds that can be obtained by the condensation by esterification of: A/ at least one alkoxylated fatty amine of formula (I), or of the product of partial or total quaternization of said alkoxylated fatty amine of formula (I): wherein R1, AO, B, n, m, s and y are as defined in the description, B/ with at least one dicarboxylic acid, or a derivative thereof, of the following formula (II): wherein D and RA are as defined in the description, C/ with at least one (alkyl)alkanolamine derivative of the following formula (III) or the product of partial or total quaternization of said (alkyl)alkanolamine derivative of the following formula (III): wherein A"O, u, u' and R7 are as defined in the description, and D/ with at least one fatty acid of the following formula (V): wherein R11 is as defined in the description. The invention further relates to the use of said compound as a surfactant, biocide, anti-corrosion agent, wetting agent, in the fields of hygiene, cosmetics, detergents, human and animal health, agrochemicals, the textile industry, the mining industry, the fertilizer industry, the bitumen industry, road construction, road maintenance and sealing, the water treatment industry, and more generally in the chemical, oil and gas industries.