Hydroxy-Amino Polymer Synthesis via DMC Catalyst
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Solution Overview
Problem
Existing methods for producing hydroxy-amino polymers limit the distance between amino and hydroxyl functionalities to no more than seven covalent bond lengths and restrict the incorporation of multiple amine groups, leading to structural limitations and by-product formation.
Innovation Solution
A process involving the reaction of an H-functional starter compound with an unsaturated cyclic carboxylic acid anhydride and an alkylene oxide, using a double metal cyanide catalyst, allows for the controlled introduction of amino groups into hydroxy-functional polymers, enabling varying distances between amino and hydroxyl functionalities and multiple amine incorporation.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Length of moving object
If existing methods are used to introduce amino groups into polymers, then amino functionality is achieved, but the distance between amino and hydroxyl groups is limited to maximum seven covalent bond lengths and multiple amine incorporation is restricted
Solution Approach 1:
The process segments the introduction of amino groups into controlled steps using a diene compound as an intermediary. The diene compound first reacts with the polymer containing electron-deficient double bonds, then subsequent amino addition occurs at controlled positions, enabling multiple amine groups to be incorporated at desired distances from hydroxyl groups rather than being limited to direct addition scenarios.
Solution Approach 2:
A diene compound serves as an intermediary between the polymer backbone and amino groups. This intermediary enables flexible structural configuration by allowing the amino groups to be introduced through the diene moiety rather than directly to the polymer, thereby achieving variable distances and multiple incorporations that would otherwise be structurally constrained.
2Adaptability or versatility
If direct addition of amines to polymers with electron-deficient double bonds is performed, then amino groups are introduced, but structural flexibility and multiple amine incorporation are limited
Solution Approach 1:
The diene compound is preliminarily incorporated into the polymer structure before amino group addition. This preliminary action creates a flexible structural platform that can subsequently accommodate multiple amino groups at controlled positions, enabling both structural flexibility and precise positioning control that direct addition methods cannot achieve.
Solution Approach 2:
The use of a diene compound introduces dynamic structural possibilities, allowing the polymer to accommodate varying numbers of amino groups at different distances from hydroxyl groups. This dynamic approach enables adaptation of the molecular structure to achieve desired property profiles rather than being constrained by fixed structural patterns.
3Quantity of substance
If conventional esterification or condensation methods are used, then double bonds are introduced into precursors, but hydroxy functionality is reduced and by-products are formed
Solution Approach 1:
The method extracts the double bond introduction step from traditional esterification/condensation pathways that sacrifice hydroxy groups. Instead, electron-deficient double bonds are directly incorporated into the polymer backbone through controlled reactions, and the diene compound subsequently adds to these double bonds, eliminating the need for hydroxy-sacrificing condensation reactions and their associated by-products.
Solution Approach 2:
The process changes the reaction parameters and mechanism from conventional esterification to a two-step addition process. This parameter change enables double bond incorporation without compromising hydroxy functionality, as the addition reactions proceed through different mechanistic pathways that do not generate the same by-products as condensation reactions.
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
This process enables the production of hydroxy-amino polymers with flexible structural configurations and increased amine functionality, avoiding by-product formation and allowing for broader property profiles, including enhanced reactivity towards isocyanate groups.
Implementation Method 1
using a double metal cyanide catalyst, allows for the controlled introduction of amino groups into hydroxy-functional polymers
Implementation Method 2
The addition of amines to polymers containing (meth)acrylate groups, including (meth)acrylate-containing polyethers, is known per se
Data Source
AI summary
The invention relates to a method for producing a hydroxy-aminopolymer, comprising the following steps: a) reacting at least one H-functional starter compound carrying at least one Zerewitinoff-active H-atom with an unsaturated cyclical carboxylic acid anhydride and at least one alkylene oxide compound in order to obtain a pre-polymer carrying hydroxyl groups; b) adding a primary amine and/or ammonia to the double bonds of the pre-polymer that carries hydroxyl groups obtained according to step a) in order to obtain the hydroxyl-aminopolymer, wherein the reaction of the H-functional starter compound with the unsaturated cyclical carboxylic acid and/or the addition of the alkylene oxide compound is carried out by using a double metal cyanide catalyst (DMC catalyst). The invention further relates to a hydroxyl aminopolymer that can be obtained according to the above-mentioned method, wherein the substance ratio between the alkylene oxide compound and the carboxylic acid anhydride is at least 1.1:1, and to the use of said hydroxyl-aminopolymer for producing a polyurethane urea polymer.