Zwitterionic Polymeric Anti-Microbial Compounds for Coating Immobilization

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Solution Overview

Problem

Existing anti-microbial polyurethane dispersions face issues with poor immobilization of anti-microbial compounds on coated surfaces, requiring substantial organic solvents in manufacturing, and limited compatibility with various polymeric binders.

Innovation Solution

Development of polymeric anti-microbial compounds with specific building blocks that provide amphiphilic character and surface active properties, allowing for improved immobilization and solubility in polar solvents, enabling their use with a wide range of binders and reducing solvent requirements.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If polyurethane dispersions comprising anti-microbial compound are used, then anti-microbial function is provided, but the anti-microbial compound is poorly immobilized on the coating surface and easily released

Engineering Contradiction:
Improveanti-microbial functionVSAvoidimmobilization of anti-microbial compound
Core Design Contradiction:
ReliabilityVSStability of the object's composition

Solution Approach 1:

The invention changes the chemical parameters of the anti-microbial compound by introducing a zwitterionic structure with both positive and negative charge centers. This structural modification enables strong ionic bonding with the polymeric binder while maintaining surface immobilization, resolving the contradiction between providing anti-microbial function and ensuring stable immobilization on the coating surface.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates a composite structure within the anti-microbial compound by combining hydrophobic and hydrophilic regions in a zwitterionic architecture. The hydrophobic regions interact with the polymeric binder while the charged regions provide ionic bonding capability, resulting in a composite material that simultaneously achieves immobilization and functional stability.

Inventive Principle:
Principle #40Composite materials

2Stability of the object's composition

If substantial amounts of organic solvents are used during dispersion manufacture, then stable dispersion is achieved, but the solvents remain present as substantial ingredients in the final product

Engineering Contradiction:
Improvedispersion stabilityVSAvoidorganic solvent content
Core Design Contradiction:
Stability of the object's compositionVSLoss of substance

Solution Approach 1:

The invention changes the solvent system parameters by transitioning from organic solvents to polar solvents (such as water or alcohols). The zwitterionic structure of the anti-microbial compound is specifically designed to be soluble in polar solvents, enabling stable dispersion formulation with reduced or eliminated organic solvent content in the final product.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention discards the use of substantial amounts of organic solvents in the final product formulation. By designing the anti-microbial compound with inherent solubility in polar solvents, the process eliminates the need for organic solvents to be present as substantial ingredients in the finished coating, thereby reducing harmful substance content.

Inventive Principle:
Principle #34Discarding and recovering

3Stability of the object's composition

If anti-microbial compound is ionically bonded to free carboxylic acid group of polyurethane, then immobilization is achieved, but application is limited to polyurethane dispersions only

Engineering Contradiction:
Improveimmobilization of anti-microbial compoundVSAvoidcompatibility with polymeric binders
Core Design Contradiction:
Stability of the object's compositionVSAdaptability or versatility

Solution Approach 1:

The invention creates a universal anti-microbial compound structure with zwitterionic characteristics that can interact with multiple types of polymeric binders through ionic bonding. The dual charge centers can bond with both acidic and basic groups on various polymer chains, making the compound compatible with polyurethanes, acrylics, vinyls, and other polymeric binders, thereby achieving broad applicability while maintaining immobilization.

Inventive Principle:
Principle #6Universality (Multi-functionality)

Solution Approach 2:

The zwitterionic structure acts as an intermediary that facilitates ionic bonding between the anti-microbial function and diverse polymeric binders. The positive and negative charge centers serve as mediating groups that can interact with different functional groups on various polymer chains, enabling the anti-microbial compound to be effectively immobilized on multiple types of binders beyond just polyurethane.

Inventive Principle:
Principle #24Intermediary (Mediator)

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 compounds effectively prevent bleeding of anti-microbial agents from coated surfaces, provide excellent permanent anti-microbial properties, and are soluble in various solvents, enhancing their compatibility and effectiveness with diverse polymeric binders while minimizing solvent use.

Implementation Method 1

The compounds according to the present invention comprise a zwitterionic structure which provides at least two charge centers per molecule, at least one positive and at least one negative charge center

Methodology Applied
Scientific EffectIonic bonding: Chemical Bonding

Implementation Method 2

the compounds according to the present invention comprise a zwitterionic structure which provides at least two charge centers per molecule, at least one positive and at least one negative charge center, having opposite signs

Methodology Applied
Scientific EffectAmphiphilic character: Amphiphiles

Implementation Method 3

providing excellent permanent anti-microbial properties, and are soluble in various solvents, enhancing their compatibility and effectiveness with diverse polymeric binders

Methodology Applied
Scientific EffectSurfactant action: Surfactant

Data Source

PatentEP3456750B1Anti microbial compounds and their use
Publication Date: 2020.04.22 CRODA INT PLC
  • EP3456750B1 patent drawing
  • EP3456750B1 patent drawing
  • EP3456750B1 patent drawing

AI summary

The present invention relates to compounds comprising building blocks according to the general formulae as shown in Fig. 1., wherein [BB1] is building block 1; [BB2] is building block 2; R1 is H or CH3, Z is a bridging group, selected from the group consisting of ester groups (-C(=O)O-) and amide groups (-C(=O)-NH-), X is an element selected from nitrogen, phosphorus, oxygen and sulfur; i is an integer which is 2 in case of nitrogen and phosphorus and 1 in case of oxygen and sulfur; Rj denotes groups which may be the same or different and comprise a C1-C20 hydrocarbyl group; Rk is a C7-C50 hydrocarbyl group; Y- is a negatively charged ion; and wherein the molar fraction of [BB2] in a molecule of the compound is between 0.3 and 1 and the weight average molecular weight of the compound is between 1.000 and 100.000 g/mol, determined with GPC. The invention further relates to compositions comprising such compounds and the use of such compounds as surfactants in a method for coating objects and in a method for preparing a latex composition.