Aliphatic Diisocyanate Crosslinking with Reactive Intermediates

Solution Overview

Problem

There is a need for alternative cross-linking agents that can produce curable compositions with properties similar to polyurethane coatings, such as durability, hardness, toughness, color stability, high gloss, and chemical resistance, while avoiding the potential concerns associated with standard polyurethane production methods.

Innovation Solution

The development of a composition comprising the reaction product of an aliphatic diisocyanate and reactive intermediates like oxazolidinones, benzoic sulfimides, and α-ketoamides, which crosslink to form curable compositions like coatings, adhesives, and films with desired properties.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If standard polyurethane production methods are used, then durability and chemical resistance are achieved, but concerns about component safety and environmental impact arise

Engineering Contradiction:
Core Design Contradiction:
ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The patent changes the chemical parameters by using alternative crosslinking agents (oxazolidinones, benzoic sulfimides, 1H-indole-2,3-diones, succinamides, N-hydroxysuccinamides, 4-hydroxy-3-methoxybenzaldehydes, α-ketoamides, piperazines, benzofuranones, 3,4-dihydroxycyclobut-3-ene-1,2-diones, squaric acid esters, anilines, and α-ketoamide phenols) instead of traditional polyurethane crosslinkers. This substitution maintains the crosslinking function while eliminating harmful components, thereby preserving durability (parameter_id: 27) while reducing component safety concerns (parameter_id: 30).

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs alternative crosslinking agents that are safer and more environmentally friendly substitutes for traditional polyurethane components. These alternative agents achieve the same crosslinking effect with reduced toxicity and environmental impact, effectively replacing harmful substances while maintaining the desired performance characteristics.

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

2Object-affected harmful factors

If alternative crosslinking agents are used, then component safety is improved, but maintaining equivalent physical properties becomes challenging

Engineering Contradiction:
Core Design Contradiction:
Object-affected harmful factorsVSManufacturing precision

Solution Approach 1:

The patent systematically evaluates multiple alternative crosslinking agents with different chemical structures and reactivities. By selecting from a diverse range of compounds (oxazolidinones, benzoic sulfimides, 1H-indole-2,3-diones, succinamides, N-hydroxysuccinamides, 4-hydroxy-3-methoxybenzaldehydes, α-ketoamides, piperazines, benzofuranones, 3,4-dihydroxycyclobut-3-ene-1,2-diones, squaric acid esters, anilines, and α-ketoamide phenols), the invention optimizes the chemical parameters to achieve both safety improvements and consistent physical properties.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates composite curable compositions by combining alternative crosslinking agents with isocyanate-reactive functional groups in specific formulations. This composite approach allows tuning of the material properties to match or exceed traditional polyurethane performance while using safer chemical components.

Inventive Principle:
Principle #40Composite materials

3Stability of the object's composition

If traditional crosslinking methods are used, then color stability and gloss are achieved, but environmental and health concerns increase

Engineering Contradiction:
Core Design Contradiction:
Stability of the object's compositionVSObject-generated harmful factors

Solution Approach 1:

The patent substitutes traditional polyurethane crosslinking chemistry with alternative chemical systems that exhibit comparable or superior color stability and gloss. The selected alternative crosslinking agents (particularly aromatic compounds like 4-hydroxy-3-methoxybenzaldehydes and heterocyclic compounds like 1H-indole-2,3-diones) provide UV resistance and color stability while eliminating the environmental and health concerns associated with conventional polyurethane components.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs environmentally friendly alternative crosslinking agents that replace harmful traditional chemicals. These substitutes maintain the aesthetic properties (color stability and gloss) while reducing environmental impact, effectively trading harmful substances for safer alternatives without sacrificing performance.

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

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 solution achieves curable compositions with durability, color stability, high gloss, and chemical resistance similar to polyurethane-based products, addressing the need for alternative cross-linking approaches that retain key performance characteristics.

Implementation Method 1

the reaction product of an aliphatic diisocyanate, and a reactive intermediate made from one selected from the group consisting of oxazolidinones, benzoic sulfimides (saccharins), 1H-indole-2,3-diones (isatins), succinamides, N-hydroxysuccinamides, 4-hydroxy-3-methoxybenzaldehydes (vanillins), α-ketoamides, piperazines, benzofuranones, 3,4-dihydroxycyclobut-3-ene-1,2-diones (squaric acids), squaric acid esters, α-ketoamides, anilines, and α-ketoamide, phenols

Methodology Applied
Scientific EffectChemical Bonding: Chemical Bonding

Data Source

PatentUS11427673B2Alternative crosslinking mechanisms for polyurethane-based systems
Publication Date: 2022.08.30
  • US11427673B2 patent drawing
  • US11427673B2 patent drawing
  • US11427673B2 patent drawing

AI summary

The present invention provides compositions comprising the reaction product of an aliphatic diisocyanate, and a reactive intermediate made from one selected from the group consisting of oxazolidinones, benzoic sulfimides (saccharins), 1H-indole-2,3-diones (isatins), succinamides, N-hydroxysuccinamides, 4-hydroxy-3-methoxybenzaldehydes (vanillins), α-ketoamides, piperazines, benzofuranones, 3,4-dihydroxycyclobut-3-ene-1,2-diones (squaric acids), squaric acid esters, α-ketoamides, anilines, and α-ketoamide, phenols. The aliphatic diisocyanate comprises one selected from the group consisting of isocyanurates, biurets, iminooxadiazine diones, urethanes, uretdiones, carbodiimides, and allophanates. The resulting compositions may be useful in producing coatings, adhesives, sealants, castings, composites and films having durability, color stability, high gloss, and chemical resistance properties similar to those made from polyurethane.