(Meth)Acrylate Urethane Oligomers With Segmented Backbones for Low Viscosity

Resolve Bottlenecks,
Find Innovative Solutions
Generate Solutions

Solution Overview

Problem

Existing (meth)acrylate-functionalized urethane oligomers do not adequately enhance the tensile properties of cured articles, such as films, and often exhibit high viscosity and poor compatibility with reactive diluents.

Innovation Solution

Development of (meth)acrylate-functionalized oligomers with a segmented or statistical oligomeric backbone structure, comprising first and second segments linked by polyisocyanate moieties, and end-capped with (meth)acrylate groups, ensuring a Hansen Solubility Parameter Distance Relative Energy Difference between segments of 4 to 9, which can be photocured to improve tensile strength and reduce viscosity.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Strength

If conventional (meth)acrylate-functionalized urethane oligomers are used, then the oligomers can be synthesized through standard methods, but the tensile properties of cured articles are not adequately enhanced

Engineering Contradiction:
Improvetensile propertiesVSAvoidperformance enhancement
Core Design Contradiction:
StrengthVSReliability

Solution Approach 1:

The oligomer backbone is divided into distinct first and second segments with different chemical compositions and properties. This segmentation allows each segment to contribute specific characteristics to the cured article, with the first segment providing tensile strength enhancement and the second segment providing complementary properties, thereby resolving the contradiction between achieving enhanced tensile properties and maintaining overall performance reliability

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The invention creates a composite oligomer structure combining two different segment types within a single oligomer molecule. This composite approach allows the integration of multiple functional characteristics - including tensile strength enhancement from the first segment and additional properties from the second segment - into a unified material that reliably delivers improved performance

Inventive Principle:
Principle #40Composite materials

2Ease of operation

If conventional (meth)acrylate-functionalized urethane oligomers are used, then the oligomers can be synthesized through standard methods, but the viscosity is high

Engineering Contradiction:
ImproveviscosityVSAvoidsynthesis complexity
Core Design Contradiction:
Ease of operationVSEase of manufacture

Solution Approach 1:

Dividing the oligomer into two segments with different molecular characteristics reduces overall viscosity while maintaining synthesizability. The segmented structure prevents excessive chain entanglement and improves fluidity, making the oligomer easier to handle and process without requiring overly complex synthesis procedures

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The invention modifies molecular parameters by selecting segment precursors with specific number average molecular weights (at least 250 daltons each) and controlling the Hansen solubility parameter difference. These parameter changes optimize the balance between viscosity reduction and synthesis feasibility, ensuring the oligomer remains manufacturable while achieving desired flow characteristics

Inventive Principle:
Principle #35Parameter changes

3Adaptability or versatility

If conventional (meth)acrylate-functionalized urethane oligomers are used, then the oligomers can be synthesized through standard methods, but compatibility with reactive diluents is poor

Engineering Contradiction:
Improvecompatibility with reactive diluentsVSAvoidperformance consistency
Core Design Contradiction:
Adaptability or versatilityVSReliability

Solution Approach 1:

The first and second segments are designed with different local chemical qualities and Hansen solubility parameters. This local quality differentiation enables the oligomer to interact favorably with various reactive diluents through specific segment-diluent interactions, improving compatibility while maintaining consistent overall performance through the complementary nature of the two segments

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The composite oligomer structure combines segments with different solubility characteristics, creating a material that can adapt to and compatibly mix with diverse reactive diluents. This composite approach enhances versatility in formulation options while preserving performance consistency through the balanced contribution of both segments

Inventive Principle:
Principle #40Composite materials

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 new oligomers provide improved tensile strength and lower viscosity, enhancing the performance of cured compositions used in coatings, adhesives, and additive manufacturing resins.

Implementation Method 1

curable compositions which function as coatings, adhesives, sealants, additive manufacturing resins, molding resins and the like

Methodology Applied
Scientific EffectPhotocuring: Photopolymerisation

Data Source

PatentUS12492283B2(meth)acrylate-functionalized oligomers and methods of preparing and using such oligomers
Publication Date: 2025.12.09 ARKEMA FRANCE SA
  • US12492283B2 patent drawing
  • US12492283B2 patent drawing

AI summary

(Meth)acrylate-functionalized oligomers having a) an oligomeric backbone comprised of first segments and second segments and b) (meth)acrylate-functionalized end groups are provided. Such oligomers are useful as components of curable compositions. The first segments, second segments and (meth)acrylate-functionalized end groups are linked together by linking moieties derived from a polyisocyanate. The first segments are residues of a first segment precursor containing a plurality of repeating units and a plurality of isocyanate-reactive functional groups and having a number average molecular weight of at least 250 daltons. The second segments are residues of a second segment precursor, different from the first segment precursor, containing a plurality of repeating units and a plurality of isocyanate-reactive functional groups and having a number average molecular weight of at least 250 daltons. The first segment and the second segment exhibit a Hansen Solubility Parameter Distance Relative Energy Difference of at least about 4 and not more than about 9.