Mixed Aryl-Alkyl Diester Plasticizer for Water-Borne Adhesives

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Solution Overview

Problem

Existing benzoate esters are limited in their ability to lower the glass transition temperature and increase viscosity in water-borne adhesives, and they are not suitable for more polar polymers, leading to restricted utility and potential cost inefficiencies.

Innovation Solution

The development of mixed alkyl/aryl diester compositions derived from benzoic acid, aliphatic monocarboxylic acid, and diols, which can be used as plasticizers, solvents, and modifiers, allowing for varying physical properties such as melting point, viscosity, and volatility by adjusting the molar ratio of aromatic to aliphatic acids and the number of carbon atoms in the diol, thereby enhancing compatibility and utility in adhesive compositions.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Temperature

If conventional benzoate esters are used as plasticizers in water-borne adhesives, then the adhesive formulation is simple, but the glass transition temperature cannot be sufficiently lowered and viscosity cannot be sufficiently increased

Engineering Contradiction:
Improveglass transition temperatureVSAvoidester composition complexity
Core Design Contradiction:
TemperatureVSDevice complexity

Solution Approach 1:

The patent employs composite ester compositions combining aromatic carboxylic acids (benzoic acid derivatives) with aliphatic carboxylic acids (C1-C3 acids such as acetic, propionic, or butyric acid) to create mixed diesters and monoesters. This composite approach allows the plasticizer to simultaneously achieve lower glass transition temperatures and higher viscosity in water-borne adhesives, resolving the limitation of conventional single-type benzoate esters.

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The patent systematically varies compositional parameters including the ratio of aromatic to aliphatic acid components, the specific chain length of aliphatic acids (C1-C3), and the molecular weight of diols to optimize plasticizer performance. By adjusting these parameters, the formulation achieves desired glass transition temperatures and viscosity levels while maintaining compatibility with water-borne adhesive systems.

Inventive Principle:
Principle #35Parameter changes

2Adaptability or versatility

If conventional benzoate esters are used, then the formulation is straightforward, but compatibility with more polar polymers is insufficient leading to restricted utility

Engineering Contradiction:
Improvecompatibility with polar polymersVSAvoidplasticizer composition complexity
Core Design Contradiction:
Adaptability or versatilityVSDevice complexity

Solution Approach 1:

The mixed ester composition combines aromatic esters (which provide compatibility with traditional polymers) and aliphatic esters (which enhance compatibility with polar polymers through their polar carbonyl groups and shorter hydrocarbon chains). This composite structure enables the plasticizer to effectively plasticize both conventional and polar polymers such as polyvinyl alcohol, polyacrylic acid, and polymethacrylic acid, significantly expanding utility.

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The patent introduces functional differentiation within the plasticizer molecule by combining aromatic rings (for structural stability and traditional polymer compatibility) with aliphatic chains containing polar carbonyl groups (for enhanced interaction with polar polymer chains). This local quality variation within the molecular structure enables broad compatibility across different polymer types.

Inventive Principle:
Principle #3Local quality

3Stress or pressure

If existing plasticizers are used to increase viscosity, then the adhesive performance is limited, but using mixed diesters requires more complex composition design

Engineering Contradiction:
ImproveviscosityVSAvoidcomposition design complexity
Core Design Contradiction:
Stress or pressureVSDevice complexity

Solution Approach 1:

The patent utilizes the strong influence of aliphatic acid chain length (C1-C3) on plasticizer viscosity and polarity. By selecting specific chain lengths and combining them with aromatic acid components in optimized ratios, the formulation achieves high viscosity necessary for adhesive applications. The presence of both polar carbonyl groups and adjustable hydrocarbon chain lengths provides fine-tuned control over viscosity while maintaining compositionality that can be systematically designed.

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 mixed diester compositions effectively lower the glass transition temperature and increase viscosity in water-borne adhesives, expanding their utility to more polar polymers while maintaining desirable properties, resulting in cost savings and improved performance.

Implementation Method 1

The present ester compositions are particularly useful as plasticizers for aqueous adhesive compositions... effectively lower the glass transition temperature

Methodology Applied
Scientific EffectPlasticization:

Implementation Method 2

increase viscosity in water-borne adhesives

Methodology Applied
Scientific EffectViscosity enhancement:

Data Source

PatentUS8207253B2Mixed aryl/alkyl diester compositions
Publication Date: 2012.06.26 EASTMAN SPECIALTIES HOLDINGS CORP

AI summary

Novel ester compositions are prepared by reacting 1) at least one diol, glycol or oligomeric glycol with 2) a mixture of at least one aromatic monocarboxylic acid and at least one aliphatic monocarboxylic acid containing from 2 to 4 carbon atoms. The compositions are effective plasticizers for a variety of polymers, particularly those employed in water-borne adhesives. The freezing point of the present ester mixtures and their efficacy as plasticizers and other types of additives and/or modifiers for a variety of polymer compositions can be varied by adjusting the relative concentrations of the aromatic and aliphatic acids used to prepare the ester composition.