Alkyl Hydroxylamines Stabilize Choline Hydroxide Color

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Solution Overview

Problem

Choline hydroxide compositions used in the agricultural chemical industry and semiconductor applications tend to decompose over time, leading to coloration and precipitation issues due to the formation of volatile components and their adducts, which existing stabilizers like sodium borohydride and hydroxylamine salts cannot effectively address at low concentrations for long-term stabilization.

Innovation Solution

The use of alkyl hydroxylamines, hydrazides, and hydrazines as stabilizers at concentrations below 1000 ppm, such as diethylhydroxylamine (DEHA) and carbodihydrazide, which react with acetaldehyde decomposition products to form non-chromophore derivatives, effectively stabilizing choline hydroxide solutions at low levels, maintaining a Gardner Color change less than 2.0 after six months.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If existing stabilizers like sodium borohydride and hydroxylamine salts are used, then some stabilization effect is achieved, but they cannot effectively prevent coloration and decomposition at low concentrations for long-term stability

Engineering Contradiction:
Improvelong-term stabilization effectivenessVSAvoidstabilizer concentration level
Core Design Contradiction:
ReliabilityVSQuantity of substance

Solution Approach 1:

The patent changes the chemical structure parameters of stabilizers by introducing nitrogen-containing functional groups (hydroxylamine, hydrazide, hydrazine moieties) to achieve superior stabilization at lower concentrations. This structural modification enables the stabilizer to effectively scavenge acetaldehyde and prevent coloration at concentrations below 1000 ppm, resolving the contradiction between long-term effectiveness and low concentration usage.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs composite stabilizer systems combining nitrogen-containing functional groups with specific molecular structures (aromatic rings, alkyl chains) to create synergistic effects. This composite approach enhances stabilization efficiency, allowing effective long-term protection at low concentrations by combining multiple functional elements within the stabilizer molecule.

Inventive Principle:
Principle #40Composite materials

2Duration of action of stationary object

If choline hydroxide is stabilized for long periods, then decomposition is prevented, but coloration occurs due to formation of volatile components and their adducts

Engineering Contradiction:
Improvestabilization durationVSAvoidcoloration and precipitation
Core Design Contradiction:
Duration of action of stationary objectVSObject-generated harmful factors

Solution Approach 1:

The patent converts the harmful acetaldehyde decomposition product into a beneficial target for stabilization by designing stabilizers that specifically react with acetaldehyde through nitrogen-containing functional groups. The acetaldehyde that would normally cause coloration and precipitation is instead captured and converted into stable adducts by the stabilizer, transforming the harm into a controlled interaction that prevents degradation.

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

Solution Approach 2:

The nitrogen-containing stabilizers act as intermediary substances between the choline hydroxide and the harmful acetaldehyde decomposition products. These stabilizers mediate the interaction by preferentially reacting with acetaldehyde to form stable complexes, thereby preventing acetaldehyde from causing coloration and precipitation while extending the stabilization duration.

Inventive Principle:
Principle #24Intermediary (Mediator)

3Reliability

If high concentrations of stabilizers like TMA are used, then short-term stabilization is achieved, but the solution turns black after one week at 40° C

Engineering Contradiction:
Improvestabilization effectivenessVSAvoidblack coloration
Core Design Contradiction:
ReliabilityVSObject-generated harmful factors

Solution Approach 1:

The patent changes the chemical composition parameters by incorporating nitrogen-containing functional groups (hydroxylamine, hydrazide, hydrazine) that fundamentally alter the stabilization mechanism. These structural changes enable the stabilizer to prevent black coloration at low concentrations by effectively scavenging acetaldehyde through nitrogen-based chemistry, avoiding the degradation issues seen with conventional stabilizers like TMA.

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

These nitrogen-based stabilizers prevent coloration and precipitation in choline hydroxide solutions, ensuring long-term stability and maintaining low color indices even at high pH levels, making them suitable for agricultural applications where low stabilizer levels are required.

Implementation Method 1

react with acetaldehyde decomposition products to form non-chromophore derivatives

Methodology Applied
Scientific EffectChemical reaction: Chemical Bonding

Implementation Method 2

prevent coloration and precipitation in choline hydroxide solutions

Methodology Applied
Scientific EffectAbsorption: Absorption (physical)

Data Source

PatentUS10264785B2Using novel amines to stabilize quaternary trialkylalkanolamines
Publication Date: 2019.04.23 HUNTSMAN PETROCHEMICAL LLC
  • US10264785B2 patent drawing
  • US10264785B2 patent drawing

AI summary

New stabilizers for solutions of choline hydroxide and related quaternary trialkylalkanolamines are disclosed. The stabilizers are alkyl hydroxylamines, hydrazines, hydrazides, or derivates thereof, including compounds containing more than one such functionality. The new stabilizers are effective at concentrations less than about 1000 ppm, and choline hydroxide solutions stabilized with the compounds described herein typically have Gardner Color change less than about 2.0 after six months at reasonable temperatures.