Carbohydrate-Derived Monomers for PET-Like Biodegradable Polymers
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Solution Overview
Problem
Current biodegradable polymers derived from renewable resources, such as polylactic acid, polybutyl succinate, and polyhydroxyalkonates, fail to meet the mechanical and processability standards required for replacing non-biodegradable plastics like polyethylene terephthalate (PET), and existing alternatives like poly(ethylene furanoate) face issues with commercialization due to multi-step reactions and non-biodegradability.
Innovation Solution
Development of polymerizable monomers from renewable resources, specifically carbohydrates, through acetalization with functionalized aldehydes, allowing for the production of polymers with good thermal and mechanical properties, including polyesters, polyamides, and other types, using a simple synthetic process.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Object-affected harmful factors
If renewable polymers like polylactic acid and polyhydroxyalkanoates are used, then environmental sustainability is improved, but mechanical properties and processability deteriorate compared to petroleum-based plastics
Solution Approach 1:
The patent changes the chemical structure parameters of renewable monomers by introducing aromatic rings and adjusting functional group positions, transforming the mechanical properties of the resulting polymers to match or exceed petroleum-based plastics while maintaining renewable sourcing
Solution Approach 2:
The patent creates composite-like structures within the polymer chains by incorporating rigid aromatic rings into the polymer backbone, combining the flexibility of renewable sources with the strength of aromatic structures to achieve both sustainability and mechanical performance
2Object-affected harmful factors
If poly(ethylene furanoate) is used as a renewable alternative to PET, then renewable resource usage is improved, but commercialization feasibility deteriorates due to complex multi-step production processes
Solution Approach 1:
The patent performs preliminary actions by pre-functionalizing carbohydrate molecules with polymerizable groups before polymerization, eliminating the need for complex multi-step synthesis routes and intensive separations required by conventional PEF production
Solution Approach 2:
The patent extracts and removes the complex multi-step synthesis sequence and intensive separation steps from the production process, achieving direct polymerization from renewable carbohydrates to simplify the overall manufacturing pathway
3Object-affected harmful factors
If poly(ethylene furanoate) is used as a renewable polymer, then renewable resource content is improved, but biodegradability deteriorates as reports indicate it is non-biodegradable
Solution Approach 1:
The patent applies local quality by incorporating biodegradable carbohydrate-derived segments at specific locations within the polymer chain, creating localized biodegradable regions that enable overall polymer biodegradation while maintaining renewable resource content
4Strength
If dianhydrohexitols like isosorbide are used to prepare renewable polyesters, then thermal and mechanical properties are improved, but reactivity deteriorates due to low reactivity of secondary alcohol groups
Solution Approach 1:
The patent changes the reactivity parameters by introducing highly reactive functional groups (carboxylic acid, aldehyde, vinyl, azide, amine) that can readily react with the secondary alcohol groups of dianhydrohexitols, overcoming the inherent low reactivity while maintaining the thermal and mechanical benefits
5Object-affected harmful factors
If isosorbide is produced by acid catalyzed dehydration of D-sorbitol, then renewable diol production is improved, but manufacturing complexity deteriorates due to laborious purification steps
Solution Approach 1:
The patent performs preliminary action by conducting the acid-catalyzed dehydration and purification steps earlier in the process chain, integrating them into the overall synthesis pathway to simplify downstream processing and reduce the number of separate purification operations required
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 monomers provide polymers with thermal and mechanical properties comparable to PET, are biodegradable, and can be manufactured directly from biomass with a straightforward process, offering a sustainable alternative to traditional plastics.
Implementation Method 1
The invention provides for a method for the preparation of the compound according to the invention or a composition comprising at least two different compounds according to the invention, having one of the structures (I), (II) or (V) wherein R1, R2, R3, R10, n, and p are as defined herein, comprising the steps of a. providing a carbohydrate or a lignocellulose-containing composition; b. adding an aldehyde optionally comprising at least one functional group selected from the group consisting of carboxylic acid, carboxylic amide, ether, alkyne, alkene, aldehyde, chloride, hydroxyl, and azide, carboxylic acid ester, aldehyde, vinyl, and amine to the carbohydrate or to the lignocellulose-containing composition to obtain a mixture; c. heating the mixture under acidic conditions
Data Source
AI summary
Described is a compound having the structure (I), (II) or (V), Formulae (I), (II), (V), wherein R1 is —H, —CH2OH or —CH(OH)CH2OH; R2 is —H, —OH, or —CH2OH; R3 is —H, —OH, or —CH2OH; n is 0 or 1; p is 0 or 1; R10 is hydrogen or a hydrocarbon moiety with 1 to 20 carbon atoms, wherein each hydrogen atom of the hydrocarbon moiety may optionally be substituted with a C1-C4-alkyl group or a halogen atom; R is either —Z—F or Y and wherein Z is a hydrocarbon moiety with 0 to 10 carbon atoms, optionally substituted with 1 to 4 C1-C4-alkyl groups or 1 to 4 halogen atoms, and F is —COOH, —CH(COOH)2, —COOR4, —CHO, —CH(CHO)2, —C2H3, —C2H, —N3, —NH2, —NHR7, —OH, —CH(CH2OH)2, wherein R4 is a C1-C4-alkyl group and R7 is a C1-C4-alkyl group and wherein Y is hydrogen or a linear, branched or cyclic organic residue having 1 to 20 carbon atoms with the proviso that if R is Y and n is 0 at least one of R1 or R2 is not hydrogen. Also described is a method for the preparation of the compound, a polymer derived from the compound as well as a method for the preparation of the polymer.