Protected Iridoid Derivatives for Stable Tanning

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Solution Overview

Problem

Existing tanning methods using aglycone forms of iridoids or seco-iridoids face limitations due to high reactivity, leading to stability, storability, and toxicity issues, and require expensive enzymatic hydrolysis for activation.

Innovation Solution

The use of protected iridoid or seco-iridoid derivatives, where the dihydropyranyloxy moiety is protected with an acyclic acetal group, which can be easily removed under acidic conditions to release the active aglycone form for tanning processes.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If aglycone forms of iridoids or seco-iridoids are used as tanning agents, then tanning effectiveness is improved, but stability and storability deteriorate due to high reactivity

Engineering Contradiction:
Improvetanning effectivenessVSAvoidstability and storability
Core Design Contradiction:
ReliabilityVSStability of the object's composition

Solution Approach 1:

The patent applies preliminary protection by introducing an acyclic acetal group to the dihydropyranyloxy moiety of iridoid or seco-iridoid compounds before tanning. This preliminary action creates a stable protected derivative that can be stored and handled safely, then activated in situ during the tanning process to provide the desired tanning effectiveness without the stability issues of the free aglycone form.

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The protected iridoid or seco-iridoid derivative acts as an intermediary form between the stable glycoside and the reactive aglycone. This intermediary compound combines the stability of protected forms with the ability to release the active aglycone form during tanning, resolving the contradiction between stability and reactivity.

Inventive Principle:
Principle #24Intermediary (Mediator)

2Reliability

If aglycone forms of iridoids or seco-iridoids are used as tanning agents, then tanning effectiveness is improved, but toxicity increases

Engineering Contradiction:
Improvetanning effectivenessVSAvoidtoxicity
Core Design Contradiction:
ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The patent applies preliminary protection by introducing an acyclic acetal group to the dihydropyranyloxy moiety of iridoid or seco-iridoid compounds before tanning. This preliminary action creates a stable protected derivative that can be stored and handled safely, then activated in situ during the tanning process to provide the desired tanning effectiveness without the stability issues of the free aglycone form.

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The protected iridoid or seco-iridoid derivative acts as an intermediary form between the stable glycoside and the reactive aglycone. This intermediary compound combines the stability of protected forms with the ability to release the active aglycone form during tanning, resolving the contradiction between stability and reactivity.

Inventive Principle:
Principle #24Intermediary (Mediator)

3Stability of the object's composition

If glycoside forms of iridoids or seco-iridoids are used, then stability and storability are improved, but activation requires expensive enzymatic hydrolysis

Engineering Contradiction:
Improvestability and storabilityVSAvoidactivation cost and complexity
Core Design Contradiction:
Stability of the object's compositionVSEase of manufacture

Solution Approach 1:

The protected iridoid or seco-iridoid derivative acts as an intermediary form between the stable glycoside and the reactive aglycone. This intermediary compound combines the stability of protected forms with the ability to release the active aglycone form during tanning, resolving the contradiction between stability and reactivity.

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The patent changes the chemical parameter of the protecting group from a glycoside to an acyclic acetal derivative. This parameter change allows the compound to be activated under mild acidic conditions rather than requiring expensive enzymatic hydrolysis, while maintaining the stability benefits of protected forms.

Inventive Principle:
Principle #35Parameter changes

4Stability of the object's composition

If glycoside forms of iridoids or seco-iridoids are used, then stability and storability are improved, but activation under mild conditions is difficult

Engineering Contradiction:
Improvestability and storabilityVSAvoidease of activation
Core Design Contradiction:
Stability of the object's compositionVSEase of operation

Solution Approach 1:

The protected iridoid or seco-iridoid derivative acts as an intermediary form between the stable glycoside and the reactive aglycone. This intermediary compound combines the stability of protected forms with the ability to release the active aglycone form during tanning, resolving the contradiction between stability and reactivity.

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The patent changes the chemical parameter of the protecting group from a glycoside to an acyclic acetal derivative. This parameter change allows the compound to be activated under mild acidic conditions rather than requiring expensive enzymatic hydrolysis, while maintaining the stability benefits of protected forms.

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

This approach provides stable, less toxic tanning agents that can be easily activated under mild conditions, enhancing the efficiency and quality of the tanning process while reducing costs.

Implementation Method 1

This acetal protecting group can be easily removed before and/or during a tanning process, typically using acidic conditions, thereby releasing the active aglycone form.

Methodology Applied
Scientific EffectHydrolysis: Hydrolysis

Implementation Method 2

The effectiveness of tanning is usually reflected by its ability to stabilize collagen, namely to limit collagen denaturation and impart good resistance to enzymatic hydrolysis.

Methodology Applied
Scientific EffectCross-linking: Chemical Bonding

Data Source

PatentEP4379068B1Iridoid or seco-iridoid derivatives and their use in a tanning process
Publication Date: 2025.06.04 HERMES SELLIER (SOCIETE PAR ACTIONS SIMPLIFIEE)
  • EP4379068B1 patent drawingFigure 1
  • EP4379068B1 patent drawingFigure 2
  • EP4379068B1 patent drawingFigure 3

AI summary

The present invention relates to the field of tanning. More particularly, the present invention relates to particular iridoid or seco-iridoid derivatives, and their use in a tanning process. It also relates to a process for cross-linking collagen using such derivatives.