Urea-Containing Silane Synthesis in Water

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Solution Overview

Problem

The existing production process for urea-containing silanes is complex and requires multiple organic solvent steps, making it inefficient and environmentally unfavorable.

Innovation Solution

A process that synthesizes urea-containing silanes without organic solvents by reacting diamines with isocyanatosilanes in water, reducing the number of process steps and eliminating the need for solvent removal and change, while achieving high yields and purity.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of manufacture

If the known production process is used, then urea-containing silanes can be produced, but the process is complex with many process steps and requires organic solvents

Engineering Contradiction:
Improveprocess complexityVSAvoidnumber of process steps
Core Design Contradiction:
Ease of manufactureVSQuantity of substance

Solution Approach 1:

The patent combines multiple separate process steps (neutralization, extraction, drying, solvent removal, solvent change, reaction, precipitation, washing) into a single integrated aqueous phase reaction process. The diamine hydrochloride salt reacts directly with isocyanatosilane in water to form the urea-containing silane product, eliminating the need for sequential processing steps and organic solvents.

Inventive Principle:
Principle #5Merging (Combining)

Solution Approach 2:

The patent changes the solvent parameter from organic solvents (CH2Cl2, THF, Pentane) to water as the reaction medium. This parameter change fundamentally simplifies the process by eliminating solvent removal steps, extraction steps, and drying steps, while maintaining product formation through the aqueous phase reaction.

Inventive Principle:
Principle #35Parameter changes

2Productivity

If organic solvents are used in the known process, then the reaction can proceed, but environmental impact increases and additional purification steps are required

Engineering Contradiction:
Improvereaction efficiencyVSAvoidenvironmental impact
Core Design Contradiction:
ProductivityVSObject-affected harmful factors

Solution Approach 1:

The patent replaces expensive, environmentally harmful organic solvents with water, which is inexpensive, non-toxic, and environmentally benign. Water serves as both the reaction medium and can be easily removed without specialized equipment, eliminating the need for costly solvent recovery systems and reducing environmental impact.

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

Solution Approach 2:

The patent converts the typically problematic aqueous environment into a beneficial reaction medium. By performing the reaction in water, the process eliminates the need for multiple solvent removal and purification steps, turning what would normally require complex handling into a simplified process that reduces environmental impact while maintaining productivity.

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

3Manufacturing precision

If multiple solvent steps are performed, then product purification can be achieved, but time consumption and process complexity increase

Engineering Contradiction:
Improveproduct purityVSAvoidprocess time
Core Design Contradiction:
Manufacturing precisionVSLoss of time

Solution Approach 1:

The patent performs preliminary neutralization of the diamine hydrochloride salt in the aqueous reaction medium before the main reaction occurs. This preliminary action ensures the diamine is in the correct form for reaction with isocyanatosilane, and the entire process including purification occurs in a single aqueous phase, eliminating the need for time-consuming sequential purification steps.

Inventive Principle:
Principle #10Preliminary action

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 process achieves high yields (>50%) of urea-containing silanes with reduced residual impurities and solvent content, simplifying the production and minimizing environmental impact, and allows for the use of urea-containing silanes as adhesion promoters and crosslinking agents.

Implementation Method 1

reacting diamines with isocyanatosilanes in water

Methodology Applied
Scientific EffectChemical reaction: Chemical Bonding

Implementation Method 2

reacting diamines with isocyanatosilanes in water

Methodology Applied
Scientific EffectSolvation: Solvation

Data Source

PatentEP2944642B1Process for preparing urea-containing silanes
Publication Date: 2017.05.10 EVONIK OPERATIONS GMBH
  • EP2944642B1 patent drawing
  • EP2944642B1 patent drawing
  • EP2944642B1 patent drawing

AI summary

The invention relates to a process for the production of urea-containing silanes of general formula I, wherein a diamine of general formula II H2N-RSSR-NH2 (II) is reacted with isocyanate silane of general formula III (R1)3Si-R-NCO (III) in water.