Isosorbide Monoesters as Broad pH Antimicrobial Preservatives

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Solution Overview

Problem

Existing preservatives used in industries such as cosmetics, pharmaceuticals, and crop protection are often expensive and require high concentrations for effective microbial protection, and many are based on synthetic materials, lacking efficacy across a broad pH range.

Innovation Solution

The use of isosorbide monoesters with specific alkyl or alkenyl groups as antimicrobially active compounds, which are more cost-effective, based on renewable raw materials, and exhibit broad-spectrum preservative performance, including fungicidal activity across a wider pH range compared to organic acids.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional preservatives are used, then microbial protection is achieved, but production cost increases and synthetic raw materials are required

Engineering Contradiction:
Improvemicrobial protectionVSAvoidproduction cost
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The patent changes the chemical structure parameters by using isosorbide monoesters with specific fatty acid chains (C6-C18) instead of conventional preservatives. This structural parameter change enables renewable raw material usage while maintaining antimicrobial efficacy, thereby reducing production cost and eliminating synthetic material dependence without compromising microbial protection

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention employs composite material structure by combining isosorbide core with various fatty acid esters to create a family of compounds with enhanced antimicrobial properties. This composite approach allows leveraging the natural antimicrobial characteristics of fatty acids while using renewable isosorbide backbone, achieving both cost reduction and effective microbial protection

Inventive Principle:
Principle #40Composite materials

2Reliability

If high concentrations of preservatives are used, then satisfactory preservation is achieved, but cost and formulation complexity increase

Engineering Contradiction:
Improvepreservation performanceVSAvoiduse concentration
Core Design Contradiction:
ReliabilityVSQuantity of substance

Solution Approach 1:

The patent changes the antimicrobial activity parameter of the preservative compounds through specific molecular structure design. The isosorbide monoesters with C6-C18 fatty acids exhibit inherently higher antimicrobial activity compared to conventional preservatives, enabling effective preservation at lower concentrations and reducing both material costs and formulation complexity

Inventive Principle:
Principle #35Parameter changes

3Ease of manufacture

If organic acids are used as preservatives, then cost is reduced, but pH range activity is limited

Engineering Contradiction:
ImprovecostVSAvoidpH range activity
Core Design Contradiction:
Ease of manufactureVSAdaptability or versatility

Solution Approach 1:

The invention changes the chemical parameter of pH range by using isosorbide monoesters that maintain antimicrobial activity across a broader pH spectrum compared to organic acids. The ester structure provides enhanced stability and activity both at low pH (3.5-6) and higher pH levels, making the preservative adaptable to diverse formulation pH requirements while maintaining cost-effectiveness through renewable raw materials

Inventive Principle:
Principle #35Parameter changes

Data Source

PatentUS9730450B2Use of isosorbide monoesters as antimicrobial active substances
Publication Date: 2017.08.15 CLARIANT INT LTD
  • US9730450B2 patent drawing
  • US9730450B2 patent drawing
  • US9730450B2 patent drawing

AI summary

The use of one or more compounds of the formula (I)in whichR is a straight-chain or branched saturated alkyl group having 5 to 11 carbon atoms or a straight-chain or branched mono- or polyunsaturated alkenyl group having 5 to 11 carbon atomsas antimicrobially active compound is described.The use is preferably in cosmetic, dermatological or pharmaceutical compositions, in crop protection formulations, in washing or cleaning compositions or in paints or coatings.