Aminosiloxane Ester Copolymer Synthesis for Hair Care Stability

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Solution Overview

Problem

Existing methods for producing amine-terminated polyorganosiloxanes for hair care applications face issues such as instability, high costs, and the presence of residual impurities like SiH or allylamine, which are undesirable for hair care products.

Innovation Solution

The development of an aminosiloxane ester copolymer, specifically formulated and processed using a combination of terminal primary amino-functional polyorganosiloxanes and bis-acryloyloxy-alkanes, which are reacted under controlled conditions to produce a stable and efficient hair care product.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If amine-terminated polyorganosiloxanes are made by condensation, then the product can be obtained, but the product suffers from instability as shown by viscosity changes and development of ammonia odor after aging

Engineering Contradiction:
ImprovestabilityVSAvoidammonia odor and viscosity changes
Core Design Contradiction:
ReliabilityVSObject-generated harmful factors

Solution Approach 1:

The invention changes the chemical structure parameters by incorporating ester groups into the polyorganosiloxane chain, creating an aminosiloxane ester copolymer with improved stability. The specific parameter change is the introduction of ester linkages between the siloxane backbone and amino groups, which prevents the degradation pathways that cause ammonia odor and viscosity changes in traditional amine-terminated polyorganosiloxanes.

Inventive Principle:
Principle #35Parameter changes

2Reliability

If primary amine terminated polyorganosiloxanes are made by equilibration, then the product can be obtained, but the process is expensive requiring costly starting materials and catalysts and multiple process steps

Engineering Contradiction:
Improveproduct qualityVSAvoidmanufacturing cost and complexity
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The invention segments the synthesis process into simpler steps using readily available starting materials. Instead of requiring complex equilibration processes with expensive catalysts, the method uses straightforward condensation reactions between amino-functional siloxanes and acrylate esters, reducing both the number of steps and the cost of materials required.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The invention employs inexpensive, commercially available starting materials such as amino-functional polydimethylsiloxane and acrylate esters, replacing the costly starting materials and catalysts traditionally required for synthesizing primary amine terminated polyorganosiloxanes. This approach uses cheap, easily obtainable chemicals to achieve the desired product.

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

3Productivity

If allylamine or its derivatives are used for hydrosilylation chemistry, then amine-terminated polyorganosiloxanes can be formed, but the product contains residual SiH or allylamine that must be removed through extensive washing

Engineering Contradiction:
Improveproduction efficiencyVSAvoidresidual impurities
Core Design Contradiction:
ProductivityVSLoss of substance

Solution Approach 1:

The invention converts the potential harm of residual impurities into a benefit by designing a synthesis pathway that inherently produces a stable, non-reactive end product. The aminosiloxane ester copolymer structure ensures that no residual SiH or allylamine groups remain after reaction, as the esterification process completes the chemical transformation, eliminating the need for extensive washing steps to remove impurities.

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

4Productivity

If ammonolysis of chloropropyl terminated siloxanes is used, then amine-terminated polyorganosiloxanes can be produced, but residual ammonium chloride salt remains requiring extensive washing to remove

Engineering Contradiction:
Improveproduction rateVSAvoidresidual salt
Core Design Contradiction:
ProductivityVSLoss of substance

Solution Approach 1:

The invention takes out the problematic salt formation step from the synthesis pathway. By using direct condensation between amino-functional siloxanes and acrylate esters, the method eliminates the ammonolysis reaction that produces ammonium chloride salt. The esterification reaction produces only water as a byproduct, which can be easily removed without extensive washing, thus extracting the harmful salt formation step from the process.

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 aminosiloxane ester copolymer provides enhanced stability and performance in hair care applications, eliminating the drawbacks of previous methods such as viscosity changes and ammonia odor, while ensuring the removal of residual impurities, thus offering a cost-effective and sustainable solution.

Implementation Method 1

When amine compound and acryl compound are mixed, there is a reaction which produces an acryl functional silicon compound. This reaction is known as the Michael-type addition.

Methodology Applied
Scientific EffectMichael-type addition: Chemical Bonding

Implementation Method 2

An emulsion comprises: (I) a liquid continuous phase comprising water, and (II) a discontinuous phase dispersed in the liquid continuous phase

Methodology Applied
Scientific EffectEmulsion: Emulsion

Data Source

PatentEP4363488B1Aminosiloxane ester copolymer and methods for the preparation and use of the copolymer
Publication Date: 2025.04.16 DOW SILICONES CORP
  • EP4363488B1 patent drawing
  • EP4363488B1 patent drawing
  • EP4363488B1 patent drawing

AI summary

An aminosiloxane ester copolymer, an emulsion containing the copolymer, and processes for making the copolymer and the emulsion are provided. The copolymer and the emulsion may be formulated into hair care compositions, such as conditioners and styling products.