Esterified Lignin Composition for Non-Polar Hydrocarbon Miscibility

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Solution Overview

Problem

Lignin-based compounds face challenges in achieving compatibility with non-polar hydrocarbons, polymers, and fillers, leading to solubility and miscibility issues, odor problems, and volatility at high temperatures, limiting their industrial applications.

Innovation Solution

A composition comprising two distinct lignin constituents, modified by covalently bonding oxygen atoms from hydroxyl groups to organic residues with 1-22 carbon atoms, ensuring a weight average molecular weight above 200 g/mol, a polydispersity index above 1.20, and specific hydroxyl and methoxyl group content, allowing high miscibility and solubility in non-polar hydrocarbons while maintaining odor neutrality.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Object-affected harmful factors

If lignin biopolymers are used to replace non-polar hydrocarbons, then environmental sustainability is improved, but solubility and miscibility in non-polar hydrocarbons deteriorates

Engineering Contradiction:
Improveenvironmental sustainabilityVSAvoidsolubility in non-polar hydrocarbons
Core Design Contradiction:
Object-affected harmful factorsVSStability of the object's composition

Solution Approach 1:

The patent applies parameter changes by modifying the chemical structure of lignin biopolymers through esterification with fatty acids. This chemical modification changes the polarity and molecular weight parameters of lignin, enabling it to dissolve in non-polar hydrocarbon solvents while maintaining its biopolymer nature and environmental sustainability.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates composite materials by combining modified lignin biopolymers with non-polar hydrocarbon solvents. The esterified lignin acts as a polymer component that is compatible with hydrocarbon-based media, forming a composite system that maintains both the biopolymer's sustainability and the hydrocarbon's solubility properties.

Inventive Principle:
Principle #40Composite materials

2Stability of the object's composition

If lignin monomers are used to improve solubility in non-polar hydrocarbons, then miscibility is improved, but vapor pressure increases causing odor and volatility issues

Engineering Contradiction:
Improvemiscibility in non-polar hydrocarbonsVSAvoidodor and volatility
Core Design Contradiction:
Stability of the object's compositionVSObject-generated harmful factors

Solution Approach 1:

The patent creates composite materials by combining modified lignin biopolymers with non-polar hydrocarbon solvents. The esterified lignin acts as a polymer component that is compatible with hydrocarbon-based media, forming a composite system that maintains both the biopolymer's sustainability and the hydrocarbon's solubility properties.

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The patent applies parameter changes by modifying the chemical structure of lignin biopolymers through esterification with fatty acids. This chemical modification changes the polarity and molecular weight parameters of lignin, enabling it to dissolve in non-polar hydrocarbon solvents while maintaining its biopolymer nature and environmental sustainability.

Inventive Principle:
Principle #35Parameter changes

3Ease of manufacture

If functional groups are introduced into lignin biopolymers to improve compatibility with polymers, then processability is improved, but solubility in non-polar hydrocarbons deteriorates

Engineering Contradiction:
Improveprocessability with polymersVSAvoidsolubility in non-polar hydrocarbons
Core Design Contradiction:
Ease of manufactureVSStability of the object's composition

Solution Approach 1:

The patent applies local quality by selectively introducing specific functional groups (ester groups from fatty acids) at specific locations on the lignin biopolymer structure. This localized modification provides the necessary compatibility with polymers for processing while maintaining overall solubility in non-polar hydrocarbons through the hydrophobic fatty acid chains.

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The patent applies parameter changes by modifying the chemical structure of lignin biopolymers through esterification with fatty acids. This chemical modification changes the polarity and molecular weight parameters of lignin, enabling it to dissolve in non-polar hydrocarbon solvents while maintaining its biopolymer nature and environmental sustainability.

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 composition achieves high miscibility and solubility in non-polar hydrocarbons, reducing volatility, and maintains mechanical properties, enabling broad industrial applications without odor issues, including partial or complete replacement of petrochemicals.

Implementation Method 1

the OH groups of the lignin or lignin derivative are in part esterified

Methodology Applied
Scientific EffectEsterification:

Implementation Method 2

The OH groups of the lignin are etherified

Methodology Applied
Scientific EffectEtherification:

Implementation Method 3

the solubility of lignin in or the miscibility with less polar solvents, such as ethyl acetate, for example, is only very low. For non-polar hydrocarbons such as alkanes

Methodology Applied
Scientific EffectHydrophobic interaction:

Data Source

PatentEP4606865A1Lignin constituents containing composition and its applications
Publication Date: 2025.08.27 HANSEN & ROSENTHAL GMBH & CO KG
  • EP4606865A1 patent drawingFigure 1
  • EP4606865A1 patent drawing
  • EP4606865A1 patent drawing

AI summary

The present invention relates to a composition comprising at least two lignin constituents A) and B), wherein at least a part of the oxygen atoms originating from OH-groups present in the chemical structure of at least one of A) and B) is covalently bonded to at least one kind of organic residues selected from organic residues comprising 1 to 22 carbon atoms, wherein the Mw of all lignin constituents is > 200 g/mol, their polydispersity index is >1.20, the sum of aromatic and aliphatic hydroxyl groups of all lignins is 0 or ≤ 2.00 mmol/g, the sum of aliphatic hydroxyl groups of all lignins is 0 or < 0.25 mmol/g, the methoxyl group content of all lignins is in a range of 1.0 wt.-% to 20.0 wt.-%, based on the total weight of all lignin constituents being present, and the number of unsubstituted aromatic C-H bonds per aromatic ring of each chemical structure of each lignin constituent is on average ≥ 2 and ≤ 4, to a process for preparing the composition, to a mixture of said composition and at least one hydrocarbon, a use of said composition in polymer-containing formulations, coating formulations, pharmaceutical formulations and cosmetic formulations, e.g., as plasticizer, plasticizer oil, and/or process oil, and to a polymer formulation comprising at least one polymer and said composition.