Spacered Urea (Meth)acrylate Synthesis for Anhydrous Adhesives

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Solution Overview

Problem

Existing urea (meth)acrylates, such as N-(2-methacryloyloxyethyl) ethylene urea (MEEU) and N-(2-methacrylamidoethyl) ethylene urea (N-MEEU), are limited by restricted synthesis methods, require aqueous solutions, and produce undesired byproducts, hindering their use in non-aqueous media and applications like 3D printing, and lack structural diversity for improved adhesion, corrosion resistance, and scrub resistance.

Innovation Solution

Synthesis of urea-containing alcohols or amines with (meth)acrylates via direct esterification, transesterification, or ester aminolysis to produce novel urea (meth)acrylates with varied structures, allowing for enhanced adhesion, corrosion protection, and scrub resistance, and enabling use in anhydrous forms without laborious purification steps.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If traditional synthesis methods for MEEU and N-MEEU are used, then wet adhesion properties are improved, but structural diversity is limited and synthesis complexity increases

Engineering Contradiction:

Improvewet adhesion propertiesVSAvoidstructural diversity

Core Design Contradiction:

ReliabilityVSAdaptability or versatility

Solution Approach 1:

The invention segments the synthesis approach by separating the urea moiety introduction from the (meth)acrylate functionalization. This is achieved through a two-step process: first introducing the urea group via isocyanate reaction, then adding the polymerizable (meth)acrylate group in a subsequent step. This segmentation enables independent optimization of each functional group and allows for diverse structural variations.

Inventive Principle:

Principle #1Segmentation

Solution Approach 2:

The invention creates a universal platform for synthesizing diverse urea-containing (meth)acrylates by using intermediate compounds with universal reactivity. The hydroxyl or amine groups in the intermediates can react with various isocyanates, and the resulting isocyanate groups can subsequently react with different (meth)acrylates, enabling one intermediate to lead to multiple final products with different properties.

Inventive Principle:

Principle #6Universality (Multi-functionality)

2Reliability

If MEEU or N-MEEU are used to improve wet adhesion, then adhesion performance is enhanced, but manufacturing complexity increases due to laborious purification steps

Engineering Contradiction:

Improveadhesion performanceVSAvoidpurification process

Core Design Contradiction:

ReliabilityVSEase of manufacture

Solution Approach 1:

The invention extracts and eliminates the problematic purification step by designing a synthesis route that produces water as the only byproduct. The esterification or aminolysis reactions with (meth)acrylic acid directly yield the desired urea (meth)acrylate and water, which can be easily removed by evaporation or phase separation, avoiding laborious purification procedures.

Inventive Principle:

Principle #2Taking out (Extraction)

Solution Approach 2:

The invention converts the potentially harmful byproducts (such as HCl from traditional methods) into beneficial water molecules through careful selection of reaction pathways. By using esterification or aminolysis with (meth)acrylic acid instead of acid chlorides or anhydrides, the harmful acidic byproducts are replaced with water, simplifying the manufacturing process.

Inventive Principle:

Principle #22Blessing in disguise (Convert harm into benefit)

3Reliability

If aqueous solutions of MEEU or N-MEEU are used, then wet adhesion is improved, but adaptability to non-aqueous media is reduced

Engineering Contradiction:

Improvewet adhesionVSAvoidcompatibility with non-aqueous media

Core Design Contradiction:

ReliabilityVSAdaptability or versatility

Solution Approach 1:

The invention changes the physical-chemical parameters of the monomer by synthesizing it in anhydrous form rather than as an aqueous solution. This parameter change (from aqueous to anhydrous state) maintains the adhesive functionality while expanding compatibility to non-aqueous media, enabling use in applications like 3D printing and solvent-free systems.

Inventive Principle:

Principle #35Parameter changes

Solution Approach 2:

Instead of accepting the conventional approach of providing urea (meth)acrylates as aqueous solutions, the invention inverts the approach by synthesizing and providing them in anhydrous form. This inversion fundamentally changes the application scope from water-based to both water-based and non-aqueous applications.

Inventive Principle:

Principle #13The other way round (Inversion)

4Productivity

If activated (meth)acrylic acid derivatives are used for synthesis, then reaction efficiency is improved, but harmful byproducts are generated

Engineering Contradiction:

Improvereaction efficiencyVSAvoidbyproduct formation

Core Design Contradiction:

ProductivityVSObject-generated harmful factors

Solution Approach 1:

The invention converts the harmful byproducts (HCl, etc.) generated by using activated derivatives into beneficial water molecules by switching to esterification or aminolysis reactions with (meth)acrylic acid. These reactions maintain high efficiency while producing only water as a byproduct, which is easily removed and environmentally benign.

Inventive Principle:

Principle #22Blessing in disguise (Convert harm into benefit)

Solution Approach 2:

The invention changes the reaction parameters by selecting different reaction pathways (esterification or aminolysis) with different byproduct profiles. By adjusting the reaction conditions and choosing appropriate reagents, the harmful byproducts are replaced with water, maintaining productivity while eliminating harmful emissions.

Inventive Principle:

Principle #35Parameter changes

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 novel urea (meth)acrylates provide improved adhesion to various substrates, enhanced corrosion protection, and increased scrub resistance, suitable for coatings and adhesives, overcoming the limitations of traditional urea (meth)acrylates by offering structural diversity and anhydrous formulations.

Implementation Method 1

Synthesis of urea-containing alcohols or amines with (meth)acrylates via direct esterification

Methodology Applied

Scientific EffectEsterification:

Implementation Method 2

Synthesis of urea-containing alcohols or amines with (meth)acrylates via direct esterification, transesterification

Methodology Applied

Scientific EffectTransesterification:

Implementation Method 3

Synthesis of urea-containing alcohols or amines with (meth)acrylates via direct esterification, transesterification, or ester aminolysis

Methodology Applied

Scientific EffectEster aminolysis:

Implementation Method 4

the polymerizable unit ultimately enables the incorporation of urea moieties into polymeric materials

Methodology Applied

Scientific EffectPolymerization:

Data Source

PatentUS12351542B2Spacered urea (meth)acrylates

Publication Date: 2025.07.08 EVONIK OPERATIONS GMBH

AI summary

A novel urea (meth)acrylate can be prepared by a process involving reacting a urea containing alcohol or amine with a (meth)acrylate, (meth)acryloyl chloride, (meth)acrylic acid, or (meth)acrylic anhydride. A binder composition includes at least one repeating unit derived from the urea (meth)acrylate. The binder composition can be used in adhesive and coating applications.