Polysiloxanes with groups containing nitrogen

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Solution Overview

Problem

Existing amino-functional polysiloxanes used in textile softening compositions lack variability in nitrogen content and chain length, leading to reduced substantivity and permanence on textiles, with existing production methods either resulting in unstable products or requiring complex synthesis to achieve desired properties.

Innovation Solution

End-capped polysiloxanes modified with lateral amino functions and additional lateral or terminal functional groups in defined ratios, allowing for adjustable nitrogen content and chain length, are produced through a condensation process involving aminoalkyl-dialkoxysilanes and hydroxy-functional polydimethylsiloxanes, ensuring stable and reproducible textile softening agents.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Adaptability or versatility

If linear polydimethylsiloxanes are terminally modified with amino groups, then amino-functional polysiloxanes can be produced, but the degree of modification is not variable and nitrogen content cannot be independently adjusted

Engineering Contradiction:
Improvevariability of nitrogen content and chain lengthVSAvoidcomplexity of production process
Core Design Contradiction:
Adaptability or versatilityVSDevice complexity

Solution Approach 1:

The invention segments the polysiloxane structure into distinct functional components: amino-functional segments (from aminoalkyl-dialkoxysilanes) and chain-length controlling segments (from hydroxy-functional polydimethylsiloxanes). This segmentation allows independent adjustment of nitrogen content and chain length by varying the ratios and types of starting materials, resolving the contradiction between adaptability and process complexity.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The invention applies local quality by introducing amino functional groups at specific lateral positions on the polysiloxane chain rather than uniform terminal modification. This localized functionalization enables precise control over nitrogen content and distribution, allowing independent adjustment of substantivity properties while maintaining chain length variability.

Inventive Principle:
Principle #3Local quality

2Reliability

If chain length is increased to extend polymer chain, then substantivity can be maintained, but viscosity becomes very high and handling becomes difficult

Engineering Contradiction:
Improvesubstantivity on textilesVSAvoidhandling ease
Core Design Contradiction:
ReliabilityVSEase of operation

Solution Approach 1:

The invention changes the structural parameters of the polysiloxane by introducing lateral amino functional groups and using end-capping with trimethylsilyl groups. This modifies the molecular architecture to reduce intermolecular interactions, thereby lowering viscosity while maintaining chain length and substantivity. The parameter change in molecular structure resolves the contradiction between reliability and ease of operation.

Inventive Principle:
Principle #35Parameter changes

3Productivity

If acid-catalyzed condensation polymerization is used, then production cost is reduced and reaction time is shortened, but hydrolytic stability decreases due to lack of end-capping

Engineering Contradiction:
Improveproduction efficiencyVSAvoidhydrolytic stability
Core Design Contradiction:
ProductivityVSReliability

Solution Approach 1:

The invention applies preliminary action by pre-forming hydroxy-functional polydimethylsiloxanes with controlled chain lengths before the condensation polymerization step. This preliminary preparation allows the subsequent acid-catalyzed reaction to proceed efficiently while ensuring the final product achieves proper end-capping and hydrolytic stability, resolving the contradiction between productivity and reliability.

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The invention uses hydroxy-functional polydimethylsiloxanes as intermediary compounds that bridge the gap between simple polysiloxane synthesis and amino-functionalized products. These intermediaries enable controlled chain length and facilitate subsequent condensation with aminoalkyl-dialkoxysilanes, achieving both high productivity and hydrolytic stability through this intermediary step.

Inventive Principle:
Principle #24Intermediary (Mediator)

4Ease of manufacture

If base-catalyzed equilibration is used for production, then amino-modified polysiloxanes can be produced, but gel-like precipitation and growth occur during handling of aqueous emulsions

Engineering Contradiction:
Improvemanufacturability of amino-modified polysiloxanesVSAvoidstorage stability and resistance to gel precipitation
Core Design Contradiction:
Ease of manufactureVSStability of the object's composition

Solution Approach 1:

The invention extracts the problematic base-catalyzed equilibration step and replaces it with acid-catalyzed condensation polymerization followed by end-capping. This extraction of the problematic process step eliminates the source of gel-like precipitation while maintaining the ability to produce amino-modified polysiloxanes, resolving the contradiction between ease of manufacture and compositional stability.

Inventive Principle:
Principle #2Taking out (Extraction)

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 resulting polysiloxanes exhibit enhanced substantivity and permanence on textiles, maintaining softening effects through multiple wash cycles and improving fabric handle and hydrophilicity, while ensuring stable storage and handling properties.

Implementation Method 1

a process in which different functional silanes can be reacted in a condensation process with terminally hydroxy-functional polydimethylsiloxanes

Methodology Applied
Scientific EffectCondensation: Condensation

Data Source

PatentEP2444447B1Polysiloxanes with groups containing nitrogen
Publication Date: 2020.03.25 EVONIK OPERATIONS GMBH
  • EP2444447B1 patent drawing
  • EP2444447B1 patent drawing
  • EP2444447B1 patent drawing

AI summary

Polysiloxane compound (I), is new. Polysiloxane compound of formula (M aD1 bD2 cD3 dD4 eT fQ g) (I) or their ionic adduct with protic reactant of formula (H +>A ->) (II), is new. M : [R2R1 2SiO 1 / 2]; D1 : [R1 2SiO 2 / 2]; D2 : [R1Si(R7NHR3)O 2 / 2]; D3 : [R1SiR4O 2 / 2]; D4 : [R1SiR5O 2 / 2]; T : [R1SiO 3 / 2]; Q : [SiO 4 / 2]; R1 : optionally branched, optionally saturated 1-30C hydrocarbon or aromatic 6-30C hydrocarbon; R2 : R1, alkoxy or OH; R3 : H or hydrocarbon substituted with N, where at least 50%, preferably at least 70% of the R2 is R1; R4 : optionally branched, saturated or olefinically unsaturated 8-30C hydrocarbon, preferably decyl, dodecyl, tetradecyl, hexadecyl or octadecyl; R5 : optionally branched, optionally saturated polar OH substituted 1-30C amide, OH-substituted 1-30C carbamate, ethoxylated 1-30C amine, 1-30C guanidine or 1-30C alkylenyl guanidine; R7 : optionally branched, optionally saturated, divalent 1-30C hydrocarbon; a : 2-20; b : 10-5000; c : 1-500; d, e : 0-500; e, g : 0-20; and A -> : anion. Provided that at least one of the indices d and e is not equal to 0 and when d is 0, then e is not equal to 0 and when e is 0, then d is not equal to 0. Independent claims are also included for: (1) a composition comprising (I); and (2) the preparation of (I).