Functional Polyesters from Renewable Monomers Through a New Reaction Mechanism

Lead Research Organisation: University of Edinburgh
Department Name: Sch of Chemistry

Abstract

The polymer industry is intimately involved in every aspect of our lives, producing commodity plastics, modern electronics, biomedical materials, and much more. However, the vast majority of these polymers are derived from petroleum resources, creating both economic uncertainty and environmental risk. Biodegradable polyesters like poly(lactic acid) have provided one of the most promising solutions to this challenge, building plastics from renewable resources through a catalysed polymerisation reaction. Despite the hype and expectation, these renewable polymers account for less than 5% of all commercial polymers.

Why this limitation? Replacing all commodity plastics is difficult because of the limited range of properties accessible with PLA and its copolymers. One strategy to overcome this final roadblock is to develop polyesters with different functional groups - however current synthetic methods provide low yields of monomer feedstocks or derive from toxic reagents. This proposal builds on an important recent discovery of a new synthetic strategy to target these structurally divergent plastics. New monomers, built entirely from renewable resources, can be ring-opened to afford plastics with a broad range of functional groups. The products have the potential to transform traditional polymer markets, potentially serving as biodegradable mimics of polystyrene, as new biodegradable feedstocks for health applications, and as commodity plastics with a significantly broader range of thermal properties. Importantly, this project will also address the first stages of monomer and polymer scale up, moving the discovery from laboratory towards an industrial scale to facilitate commercialisation and materials testing of the new plastics.

Planned Impact

Who will benefit from this research?
(1) The UK polymer industry and their global partners.
(2) Residents of the UK and abroad.
(3) The academic community and future employers of trained highly qualified personnel.

How will they benefit from this research?

(1) The UK polymer industry employs nearly 300,000 people and has annual sales worth over 2% of UK GDP. These polymer products are predominantly derived from petroleum resources and are commodity polymers with narrow profit margins. Biodegradable polymers are increasingly considered as eco-friendly alternatives to polyolefin materials, but properties often do not meet desired specifications. We are developing a simple, scalable strategy to diversify the UK polymer base, a strategy essential to continued economic growth in the polymer sector. More specifically, we are developing polyesters materials with applications in the commodity and specialty industries, and have already attracted significant interest from industry who will assess and advise on our progress. Importantly, in initial discussions it is apparent that each company seeks a different target - the broad scope of this strategy has the potential to deliver impact in multiple industries from packaging to healthcare to specialty polymers. The four partners will form an industrial advisory board and engage with us during the course of this project (see letters of support from Revolymer, Dart, Synthomer and DuPont).

(2) There are clear environmental and economic factors driving UK's global leading efforts to promote sustainability. Our efforts to develop bio-sourced speciality plastics will impact these goals. A key message to policy makers and the general public, especially with the growing strength the of UK's petroleum industry, is that environmental progress and sustainability can be paired with economic diversification and efficient use of resources. This proposal develops biodegradable polymers with a clean and green reaction, and importantly is flexible enough to install a range of functional groups. All of our systems are designed to degrade. By proving the utility of this strategy on a UK scale it is expected that IP may be out-licensed to the larger global polymer community and to global partners to further increase the impact of the research. In particular, the biodegradable polystyrene target of isotactic poly(mandelic acid) is a key area of sustainable growth.

In the long term, this will have a significant impact on the general public as well. We envisage three potential long-term benefits from this research program: (i) Less waste, less toxicity and improved sustainability for the production of specialty plastics will lead to safer products and reduced waste. (ii) The jobs in the polymer and manufacturing sectors that drive our economy will be more secure if new, diverse polymer products emerge through commercialisation of these polymer functionalisation strategies. (iii) New products, new plastics and new materials with improved properties and new-to-the-world applications will be developed, providing advances in our livelihoods. Communicating these benefits of a new world plastics industry is an essential step.

(3) As outlined in the academic beneficiaries section, we are developing a platform for global researchers to exploit. In addition, an important impact of this research programme will be the training of the postdoctoral researchers involved in the project, who will become specialist in the interfacial areas of small molecule catalysis and polymer synthesis, broadening their experience, employability and leadership.

Related Projects

Project Reference Relationship Related To Start End Award Value
EP/P026095/1 01/08/2017 30/12/2018 £497,594
EP/P026095/2 Transfer EP/P026095/1 01/01/2019 31/01/2020 £214,899
 
Title Think Plastic: Materials and Making 
Description Exhibition at Royal Botanical Gardens in Edinburgh. The 'Think Plastic: Materials and Making' exhibition brings together artists and scientists to explore the possibilities of transferring sustainable, recyclable and environmentally responsible plastics from the laboratory into artwork. Through their collaborations, the artists invite us to follow them in reconsidering our relationship with plastic by exploring the intriguing and complex world of this amazing, but controversial, substance. I led the artist team as they understood their new material landscape. 
Type Of Art Artwork 
Year Produced 2020 
Impact 4-month exhibition on plastics, sparking conversations around sustainability, permanence, circularity and our ideas of waste. 
URL https://www.rbge.org.uk/whats-on/think-plastic-materials-and-making/34337
 
Description We have developed the ROP of dioxalone monomers, including the scale-up of poly(mandelic acid) synthesis as a biodegradable polystyrene mimic. We have discovered a competing reaction which affords an immortal polymerisation which can be overcome by using a unique dynamic vacuum polymerisation set-up. We have also developed a family of new monomers that allows for the retention of the acetal linkage to give polymers with faster degradation rates. The ability to scale these reactions up in large reactors has enabled us to work with partners on exploring the properties of this work, including as high Tg thermoplastics and short chain viscosity modifiers. We have also developed a next-generation family of monomers with pendant rings and interesting thermal properties - this has opened up an additional area of academic research following on from the original applications.
Exploitation Route We are exploring the development of the poly(mandelic acid) materials with a number of industry partners. We are exploring our ability to exploit the immortal polymerisation to make short chain oligomeric materials with a number of industry partners. Both projects have momentum pushing towards KT into industry.
Sectors Agriculture, Food and Drink,Chemicals,Environment,Manufacturing, including Industrial Biotechology

 
Description This work cemented our reputation in sustainable materials, giving me a platform to talk to the public and policy makers to ensure the right innovations and legislations are being pursued. It has opened doors to collaborate with social scientists to explore the realities around plastic waste with the general public. In parallel, we have been translating the work into industry, as shown by the specific industry partnerships. In addition to those reported, we're negotiating a number of additional contracts.
First Year Of Impact 2019
Sector Chemicals,Education,Environment,Manufacturing, including Industrial Biotechology,Retail
Impact Types Societal,Economic,Policy & public services

 
Description Cryo-FIB-SEM-CT: a 'three-in-one' imaging facility for opaque soft matter
Amount £1,313,346 (GBP)
Funding ID EP/P030564/1 
Organisation Engineering and Physical Sciences Research Council (EPSRC) 
Sector Public
Country United Kingdom
Start 04/2017 
End 03/2018
 
Description In-bottle Sustainable Formulations - University of Manchester and Unilever
Amount £148,000 (GBP)
Organisation Unilever 
Sector Private
Country United Kingdom
Start 10/2019 
End 10/2020
 
Description RE3 - Rethinking Resources and Recycling
Amount £801,550 (GBP)
Funding ID EP/S025200/1 
Organisation Engineering and Physical Sciences Research Council (EPSRC) 
Sector Public
Country United Kingdom
Start 01/2019 
End 06/2020
 
Description University of Manchester and Superglass Insulation Limited
Amount £182,824 (GBP)
Funding ID 511440 
Organisation Innovate UK 
Sector Public
Country United Kingdom
Start 04/2019 
End 04/2022
 
Description BASF 
Organisation BASF
Country Germany 
Sector Private 
PI Contribution PDRA has also been conducting semi-structured interview to identify their major concerns and issues with the plastic recycling industry
Collaborator Contribution Took part in semi-structured interviews and attended Discussion Day workshop
Impact BASF
Start Year 2019
 
Description Unilever 
Organisation Unilever
Country United Kingdom 
Sector Private 
PI Contribution Invited to contribute to several workshops and meetings. Gave presentations on their strength and concerns in the plastics recycling industry. PDRA has also been conducting semi-structured interview to identify their major concerns and issues with the plastic recycling industry.
Collaborator Contribution Took part in several workshops during work packages 1 and 2 of the RE3 Project. Gave semi-structured interviews and attended Discussion Day workshop for the One Bin project. Providing packaging materials, industrial expertise and knowledge surrounding current materials used in packaging and their shortcomings for the Degradables project
Impact Unilever have signed an NDA and are a confirmed project partners who wish to continue to explore the One Bin project with us including applications for further funding
Start Year 2019
 
Description Disruptive Innovation Festival 
Form Of Engagement Activity A talk or presentation
Part Of Official Scheme? No
Geographic Reach International
Primary Audience Public/other audiences
Results and Impact Participation in Disruptive Innovation Festival event with Mike Werner (Google's sustainable chemistry champion) discussing materials, plastics and sustainability.
Year(s) Of Engagement Activity 2018
 
Description Greater Manchester Green Summit 2019 
Form Of Engagement Activity A talk or presentation
Part Of Official Scheme? No
Geographic Reach Regional
Primary Audience Policymakers/politicians
Results and Impact Plenary Lecture for Green Summit of Greater Manchester Combined Authority on circular plastics. Over 500 attendees at lecture, plus follow-on sandpit event.
Year(s) Of Engagement Activity 2019
 
Description Sustainable Artists Collaboration / Royal Botanical Gardens 
Form Of Engagement Activity Participation in an activity, workshop or similar
Part Of Official Scheme? No
Geographic Reach Local
Primary Audience Industry/Business
Results and Impact Working with ceramicists and fibre artists on improving sustainability in their artwork through use of sustainable plastics and polymers. Integrating materials from Royal Botanical Garden into research.
Year(s) Of Engagement Activity 2017,2018