Hydroxymethylcarboxamido-Substituted Silanole for Stable Polymers

Resolve Bottlenecks,
Find Innovative Solutions
Generate Solutions

Solution Overview

Problem

Hydroxysilanes are challenging to produce in high purity and exhibit poor storage stability due to self-condensation, limiting their use in silane-functional polymers, which are needed for applications like adhesives and coatings.

Innovation Solution

A hydroxysilane of the formula (I) is synthesized using readily available commercial raw materials, with a hydroxyl group of high reactivity and improved storage stability, allowing it to be used as an adhesion promoter and crosslinker in curable compositions, particularly reacting with isocyanates to form thermally stable silane-functional compounds.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If hydroxysilanes are produced using conventional methods, then they can be used as adhesion promoters and crosslinkers, but they exhibit poor storage stability due to self-condensation and low purity

Engineering Contradiction:
Improvestorage stabilityVSAvoidpurity
Core Design Contradiction:
ReliabilityVSManufacturing precision

Solution Approach 1:

The patent changes the chemical structure parameters by introducing a hydroxymethylcarboxamido group with specific substituents (R1a, R1b, R2, R3) that modify the reactivity and stability characteristics of the hydroxysilane, enabling high purity production and improved storage stability simultaneously

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates a composite molecular structure combining silane group, hydroxyl group, and hydroxymethylcarboxamido group in a specific configuration that prevents self-condensation while maintaining reactivity, achieving both high purity and storage stability

Inventive Principle:
Principle #40Composite materials

2Ease of manufacture

If mercaptosilanes are used to form silane-functional compounds with isocyanates, then the compounds can be produced easily, but they have unpleasant odor and form thiourethanes with low thermal stability

Engineering Contradiction:
Improveease of conversion with isocyanatesVSAvoidthermal stability
Core Design Contradiction:
Ease of manufactureVSTemperature

Solution Approach 1:

The patent changes the functional group from mercapto to hydroxymethylcarboxamido, fundamentally altering the chemical parameters to achieve high thermal stability in the resulting urethane bonds while eliminating unpleasant odors and maintaining ease of manufacture

Inventive Principle:
Principle #35Parameter changes

3Ease of manufacture

If aminosilanes are used to form silane-functional compounds with isocyanates, then the compounds can be produced easily, but they form ureas with high viscosity and limited heat resistance

Engineering Contradiction:
Improveease of conversion with isocyanatesVSAvoidheat resistance
Core Design Contradiction:
Ease of manufactureVSStrength

Solution Approach 1:

The patent changes the amino group to a hydroxymethylcarboxamido group, modifying the chemical parameters to produce urethanes with moderate viscosity and superior heat resistance, while maintaining ease of conversion with isocyanates

Inventive Principle:
Principle #35Parameter changes

4Ease of manufacture

If known hydroxysilanes from US Pat. No. 5,587,502 are used, then they can be produced, but they are of too low purity and have low hydroxyl group reactivity

Engineering Contradiction:
Improveproduction capabilityVSAvoidpurity
Core Design Contradiction:
Ease of manufactureVSManufacturing precision

Solution Approach 1:

The patent changes the molecular structure by introducing the hydroxymethylcarboxamido substituent with specific radical configurations that enhance both the purity of the product and the reactivity of the hydroxyl group, overcoming the limitations of previously known hydroxysilanes

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 hydroxysilane enables the production of silane-functional polymers with excellent strength, elasticity, and heat resistance, providing effective adhesion to various substrates and maintaining stability over time.

Implementation Method 1

reacting it with isocyanates to form thermally stable silane-functional compounds

Methodology Applied
Scientific EffectChemical reaction (hydroxyl-isocyanate addition): Chemical Bonding

Implementation Method 2

They serve, among other things, as adhesion promoters or crosslinkers

Methodology Applied
Scientific EffectHydrolysis: Hydrolysis

Implementation Method 3

crosslinkable by means of moisture

Methodology Applied
Scientific EffectCondensation reaction: Condensation

Implementation Method 4

The polymers obtained in this way quickly cure with moisture to form elastic materials

Methodology Applied
Scientific EffectMoisture-curing: Chemical Bonding

Data Source

PatentEP3027628B1Hydroxymethylcarboxamido-substituted silanole for hardenable silane-terminating polymers
Publication Date: 2020.07.15 SIKA TECH AG
  • EP3027628B1 patent drawing
  • EP3027628B1 patent drawing
  • EP3027628B1 patent drawing

AI summary

The present invention relates to specific hydroxysilanes of formula (I), a method for the production thereof, the use thereof as a constituent of moisture-curing compositions, and silane-functional compounds produced therefrom, in particular silane-functional polymers and isocyanatosilanes. The hydrosilanes can be produced in a simple process with a high degree of purity and are storage-stable after production. Production from the reaction of lactides with aminosilanes is particularly advantageous. Hydroxysilane of formula (I), where n is 1 or 2. The other variables are as defined in the claims.