1,3-diketoamide polymers for self-curing low-VOC coatings
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Solution Overview
Problem
Current low-VOC coatings face challenges with hydrolytic instability and require additional treatments like heat or UV light for cross-linking, which limits their application and adds costs, while existing self-curing coatings with additives can degrade and affect the final coating's color and odor.
Innovation Solution
Development of 1,3-diketoamide functional polymers with vinyl ether groups that can be polymerized to create self-curing coatings, offering enhanced hydrolytic stability and thermal resistance without the need for additional treatments, using monomers like 3-oxo-N-(3-(vinyloxy)propyl)butanamide and copolymerizable monomers for improved performance.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Object-generated harmful factors
If water-based systems or low solvent/high solids formulations are used as low-VOC alternatives, then VOC emissions are reduced, but the coatings require additional heat or UV light treatment for cross-linking which limits application and increases cost
Solution Approach 1:
The polymer contains built-in auto-oxidizing functionality that enables self-curing without external heat or UV treatment. The 1,3-diketoamide groups spontaneously cross-link through oxidation in air, making the system self-sufficient and eliminating the need for additional curing equipment or energy input.
Solution Approach 2:
The invention changes the chemical structure parameter by incorporating 1,3-diketoamide functional groups into the polymer backbone, which fundamentally alters the curing mechanism from requiring external energy input to spontaneous auto-oxidation, thereby resolving the contradiction between low VOC and simple application.
2Device complexity
If AAEM-based self-curing coatings are used, then additional cross-linking treatment is eliminated, but the coatings become hydrolytically labile and may degrade under hydrolyzing conditions
Solution Approach 1:
The invention changes the chemical structure by replacing the hydrolytically unstable AAEM groups with 1,3-diketoamide functional groups that possess inherent hydrolytic stability while retaining auto-oxidizing capability, thus simultaneously maintaining both self-curing property and compositional stability.
Solution Approach 2:
The patent replaces the unstable AAEM-based polymer structure with a more stable 1,3-diketoamide polymer structure that does not require protective additives, effectively substituting a degradable system with a durable one while maintaining the self-curing mechanism.
3Stability of the object's composition
If additives such as ammonia are added to AAEM-based coatings to minimize degradation, then hydrolytic stability is improved, but the color and odor of the final coating are adversely impacted
Solution Approach 1:
The invention extracts and eliminates the need for ammonia or other protective additives by fundamentally changing the polymer chemistry to use hydrolytically stable 1,3-diketoamide groups, thereby removing the source of the problem that would otherwise require additive-based solutions that compromise color and odor.
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 1,3-diketoamide functional polymers provide hydrolytically stable, self-curing coatings that maintain hardness and chemical resistance, achieving high gel fraction without additional cross-linking agents, thus overcoming the limitations of existing low-VOC coatings.
Implementation Method 1
subjecting at least one 1,3-diketoamide functional monomer having a vinyl ether group, or precursors thereto, to polymerization to thereby provide a polymer comprising 1,3-diketoamide functional moieties
Implementation Method 2
a few 'self-curing' coatings have been developed that utilize an auto-oxidizing polymer, such as those containing the monomer Acetoacetoxyethyl methacrylate (AAEM), which cross-links in the absence of any additional treatment
Data Source
AI summary
A 1,3-diketoamide functional monomer represented by the following formula (1):wherein R and Y are independently selected from the group consisting of hydrogen, an alkyl group having from 1 to 10 carbon atoms, an aryl group having from 6 to 20 carbon atoms, and an aralkyl group having from 7 to 20 carbon atoms; and wherein X and Z are independently selected from the group consisting of an alkyl group having from 1 to 10 carbon atoms, an aryl group having from 6 to 20 carbon atoms, and an aralkyl group having from 7 to 20 carbon atoms. Also disclosed are emulsion, suspension, and solution polymers comprising residues from the 1,3-diketoamide functional monomer of formula 1 and, optionally, one or more additional ethylenically unsaturated monomers. Both latex and self-curing coating compositions described herein exhibit excellent hydrolytic stability, including increased retention of 1,3-diketo functionality.