Polymers from sugars and unsaturated fatty acids: ADMET polymerisation of monomers derived from d -xylose, d -mannose and castor oil

Piccini, Marco; Leak, David J.; Chuck, Christopher J.; Buchard, Antoine

doi:10.1039/c9py01809c

Cited by 55biodegradable polymer synthesis and propertiesPolymer composites and self-healingCatalysis for Biomass Conversion

Polymers from sugars and unsaturated fatty acids: ADMET polymerisation of monomers derived from d -xylose, d -mannose and castor oil

Open access

Piccini, Marco, Leak, David J., Chuck, Christopher J., Buchard, Antoine·2020·Polymer Chemistry

DOI 10.1039/c9py01809c

Open this paper in CoChat — free account Open PDF

Abstract

High molecular weight renewable polyesters are synthesised from an unsaturated fatty acid and structurally unmodified, hemicellulosic sugars, with post-polymerisation modification inducing semicrystallinity and allowing casting of transparent films.

The claims and statistics of this paper haven’t been checked yet.

Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.

Integrity signals

Registry

Crossref · 10.1039/c9py01809c

Cites

42 of 42 references verified0 citation errors · 0 not checkable

Statistics

Claims the paper makes

The claims and statistics of this paper haven’t been checked yet.

Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.

Claims other papers make about this one

Each is checked against this paper’s own text: does it say what the citing paper says it does?

For lactide, ε-caprolactone (Cap) has proven to be a suitable counterpart.
“For lactide (LL), ϵ‐caprolactone (in this publication: Cap) has proven to be a suitable counterpart. [9]”
From Master of Chaos and Order: Opposite Microstructures of PCL‐co‐PGA‐co‐PLA Accessible by a Single Catalyst** (2022) · cites this paper as [9]

Self-check

Percentages, sums and reported differences re-computed from the paper’s own numbers.

The self-check needs the paper’s full text.

Sustainable polymers from renewable resources
Zhu, Y., Romain, C., & Williams, C. K. (2016) · Nature · doi:10.1038/nature21001 · Cited by 2,762 · see citing works
Monomers, Polymers and Composites from Renewable Resources
Belgacem, M. N., & Gandini, A. (2008) · Elsevier eBooks · doi:10.1016/b978-0-08-045316-3.x0001-4 · Cited by 1,497 · see citing works
Biopolymers from Renewable Resources
Kaplan, D. L. (1998) · Springer eBooks · doi:10.1007/978-3-662-03680-8 · Cited by 982 · see citing works
Plant oils: The perfect renewable resource for polymer science?!
de Espinosa, L. M., & Meier, M. A. R. (2010) · European Polymer Journal · doi:10.1016/j.eurpolymj.2010.11.020 · Cited by 646 · see citing works
From monomers to polymers from renewable resources: Recent advances
Gandini, A., & Lacerda, T. M. (2015) · Progress in Polymer Science · doi:10.1016/j.progpolymsci.2014.11.002 · Cited by 621 · see citing works
4-Dialkylaminopyridines: super acylation and alkylation catalysts
Scriven, E. F. V. (1983) · Chemical Society Reviews · doi:10.1039/cs9831200129 · Cited by 573 · see citing works
Production of bio-based 2,5-furan dicarboxylate polyesters: Recent progress and critical aspects in their synthesis and thermal properties
Papageorgiou, G. Z., Papageorgiou, D. G., Terzopoulou, Z. N., & Bikiaris, D. Ν. (2016) · European Polymer Journal · doi:10.1016/j.eurpolymj.2016.08.004 · Cited by 459 · see citing works
Isosorbide as a Renewable Platform chemical for Versatile Applications—Quo Vadis?
Rose, M., & Palkovits, R. (2011) · ChemSusChem · doi:10.1002/cssc.201100580 · Cited by 440 · see citing works
Polymers from sugars: cyclic monomer synthesis, ring-opening polymerisation, material properties and applications
Gregory, G. L., López‐Vidal, E. M., & Buchard, A. (2017) · Chemical Communications · doi:10.1039/c6cc09578j · Cited by 146 · see citing works
Self-citation
Polycarbonates Derived from Glucose via an Organocatalytic Approach
Mikami, K., Lonnecker, A. T., Gustafson, T. P., Zinnel, N. F., Pai, P., Russell, D. H., & Wooley, K. L. (2013) · Journal of the American Chemical Society · doi:10.1021/ja402319m · Cited by 132 · see citing works
Use of a Renewable and Degradable Monomer to Study the Temperature-Dependent Olefin Isomerization during ADMET Polymerizations
Fokou, P. A., & Meier, M. A. R. (2009) · Journal of the American Chemical Society · doi:10.1021/ja808679w · Cited by 131 · see citing works
Acyclic Diene Metathesis with a Monomer from Renewable Resources: Control of Molecular Weight and One‐Step Preparation of Block Copolymers
Rybak, A., & Meier, M. A. R. (2008) · ChemSusChem · doi:10.1002/cssc.200800047 · Cited by 127 · see citing works
Green Polymerization Methods
(2011) · Wiley eBooks · doi:10.1002/9783527636167 · Cited by 123 · see citing works
Isosorbide-based Polymethacrylates
Gallagher, J. J., Hillmyer, M. A., & Reineke, T. M. (2015) · ACS Sustainable Chemistry & Engineering · doi:10.1021/sc5008362 · Cited by 106 · see citing works
Polymers from Sugars and CO2: Synthesis and Polymerization of a d -Mannose-Based Cyclic Carbonate
Gregory, G. L., Jenisch, L. M., Charles, B., Kociok-Köhn, G. I., & Buchard, A. (2016) · Macromolecules · doi:10.1021/acs.macromol.6b01492 · Cited by 99 · see citing works
Self-citation
Poly-amido-saccharides: Synthesis via Anionic Polymerization of a β-Lactam Sugar Monomer
Dane, E. L., & Grinstaff, M. W. (2012) · Journal of the American Chemical Society · doi:10.1021/ja305900r · Cited by 94 · see citing works
Versatile Copolymers from [ l ]-Lactide and [ d ]-Xylofuranose
Chen, X., & Gross, R. A. (1998) · Macromolecules · doi:10.1021/ma980895o · Cited by 93 · see citing works
Sustainable Polyesters Derived from Glucose and Castor Oil: Building Block Structure Impacts Properties
Shearouse, W. C., Lillie, L. M., Reineke, T. M., & Tolman, W. B. (2015) · ACS Macro Letters · doi:10.1021/acsmacrolett.5b00099 · Cited by 87 · see citing works
Polymers from sugars and CO 2 : ring-opening polymerisation and copolymerisation of cyclic carbonates derived from 2-deoxy- d -ribose
Gregory, G. L., Kociok-Köhn, G. I., & Buchard, A. (2017) · Polymer Chemistry · doi:10.1039/c7py00236j · Cited by 78 · see citing works
Self-citation
Aliphatic Polycarbonates with Controlled Quantities of d -Xylofuranose in the Main Chain
Shen, Y., Chen, X., & Gross, R. A. (1999) · Macromolecules · doi:10.1021/ma990029r · Cited by 72 · see citing works
Polycarbonates from Sugars: Ring-Opening Polymerization of 1,2-O-Isopropylidene- d -Xylofuranose-3,5- Cyclic Carbonate (IPXTC)
Shen, Y., Chen, X., & Gross, R. A. (1999) · Macromolecules · doi:10.1021/ma981791g · Cited by 70 · see citing works
Structure/property relationships in copolymers comprising renewable isosorbide, glucarodilactone, and 2,5-bis(hydroxymethyl)furan subunits
Lillie, L. M., Tolman, W. B., & Reineke, T. M. (2017) · Polymer Chemistry · doi:10.1039/c7py00575j · Cited by 68 · see citing works
Advancing the Development of Highly-Functionalizable Glucose-Based Polycarbonates by Tuning of the Glass Transition Temperature
Song, Y. H., Ji, X., Dong, M., et al. (2018) · Journal of the American Chemical Society · doi:10.1021/jacs.8b10675 · Cited by 66 · see citing works
Glycolipid Polymer Synthesized from Natural Lactonic Sophorolipids by Ring-Opening Metathesis Polymerization
Gao, W., Hagver, R., Shah, V., Xie, W., Gross, R. A., Ilker, M. F., Bell, C., Burke, K. A., & Coughlin, E. B. (2006) · Macromolecules · doi:10.1021/ma0620159 · Cited by 57 · see citing works
Organocatalyzed ROP of a Glucopyranoside Derived Five-Membered Cyclic Carbonate
Felder, S. E., Redding, M. J., Noël, A., et al. (2018) · Macromolecules · doi:10.1021/acs.macromol.7b01785 · Cited by 56 · see citing works
Functionalized Polylactides: Preparation and Characterization of [ l ]-Lactide-co-Pentofuranose
Kumar, R., Gao, W., & Gross, R. A. (2002) · Macromolecules · doi:10.1021/ma020041a · Cited by 53 · see citing works
Synthetic, Functional Thymidine-Derived Polydeoxyribonucleotide Analogues from a Six-Membered Cyclic Phosphoester
Tsao, Y.-Y. T., & Wooley, K. L. (2017) · Journal of the American Chemical Society · doi:10.1021/jacs.7b01116 · Cited by 49 · see citing works
CO 2 -Driven stereochemical inversion of sugars to create thymidine-based polycarbonates by ring-opening polymerisation
Gregory, G. L., Hierons, E. M., Kociok-Köhn, G. I., Sharma, R. I., & Buchard, A. (2017) · Polymer Chemistry · doi:10.1039/c7py00118e · Cited by 48 · see citing works
Self-citation
Combined Molecular Dynamics Simulations and Experimental Studies of the Structure and Dynamics of Poly-Amido-Saccharides
Chin, S. L., Lu, Q., Dane, E. L., Domı́nguez, L., McKnight, C. J., Straub, J. E., & Grinstaff, M. W. (2016) · Journal of the American Chemical Society · doi:10.1021/jacs.6b01837 · Cited by 43 · see citing works
Functional Polycarbonate of a d -Glucal-Derived Bicyclic Carbonate via Organocatalytic Ring-Opening Polymerization
Lonnecker, A. T., Lim, Y. H., & Wooley, K. L. (2017) · ACS Macro Letters · doi:10.1021/acsmacrolett.7b00362 · Cited by 40 · see citing works
Synthesis of Altrose Poly-amido-saccharides with β-N-(1→2)- d -amide Linkages: A Right-Handed Helical Conformation Engineered in at the Monomer Level
Xiao, R., Dane, E. L., Zeng, J., et al. (2017) · Journal of the American Chemical Society · doi:10.1021/jacs.7b07405 · Cited by 40 · see citing works
Ring-Opening Metathesis Polymerization of a Naturally Derived Macrocyclic Glycolipid
Peng, Y., Decatur, J. D., Meier, M. A. R., et al. (2013) · Macromolecules · doi:10.1021/ma400291c · Cited by 39 · see citing works
A Synthetic Bioinspired Carbohydrate Polymer with Mucoadhesive Properties
Balijepalli, A. S., Sabatelle, R. C., Chen, M., et al. (2019) · Angewandte Chemie International Edition · doi:10.1002/anie.201911720 · Cited by 33 · see citing works
Glycolipid Biomaterials: Solid-State Properties of a Poly(sophorolipid)
Zini, E., Gazzano, M., Scandola, M., et al. (2008) · Macromolecules · doi:10.1021/ma800496f · Cited by 31 · see citing works
Sugar-based bicyclic monomers for aliphatic polyesters: a comparative appraisal of acetalized alditols and isosorbide
Zakharova, E. A., de Ilarduya, A. M., León, S., & Muñoz‐Guerra, S. (2016) · Designed Monomers & Polymers · doi:10.1080/15685551.2016.1231038 · Cited by 30 · see citing works
Poly(sophorolipid) Structural Variation: Effects on Biomaterial Physical and Biological Properties
Peng, Y., Munoz‐Pinto, D. J., Chen, M., Decatur, J. D., Hahn, M. S., & Gross, R. A. (2014) · Biomacromolecules · doi:10.1021/bm501255j · Cited by 26 · see citing works
Biologically Active Branched Polysaccharide Mimetics: Synthesis via Ring-Opening Polymerization of a Maltose-Based β-Lactam
Xiao, R., Zeng, J., & Grinstaff, M. W. (2018) · ACS Macro Letters · doi:10.1021/acsmacrolett.8b00302 · Cited by 24 · see citing works
ADMET polymerization of α,ω-unsaturated glycolipids: synthesis and physico-chemical properties of the resulting polymers
Hibert, G., Grau, E., Pintori, D., et al. (2017) · Polymer Chemistry · doi:10.1039/c7py00788d · Cited by 23 · see citing works
Regioisomeric Preference in Ring-Opening Polymerization of 3′,5′-Cyclic Phosphoesters of Functional Thymidine DNA Analogues
Tsao, Y.-Y. T., Smith, T. H., & Wooley, K. L. (2018) · ACS Macro Letters · doi:10.1021/acsmacrolett.7b00858 · Cited by 23 · see citing works
A Synthetic Bioinspired Carbohydrate Polymer with Mucoadhesive Properties
Balijepalli, A. S., Sabatelle, R. C., Chen, M., et al. (2019) · Angewandte Chemie · doi:10.1002/ange.201911720 · Cited by 20 · see citing works
Ring‐Opening Metathesis Polymerization of Biomass‐Derived Levoglucosenol
Debsharma, T., Behrendt, F. N., Laschewsky, A., et al. (2019) · Angewandte Chemie · doi:10.1002/ange.201814501 · Cited by 17 · see citing works
Organometallics and Renewables
Meier, M. A. R., Bruijnincx, P. C. A., & Weckhuysen, B. M. (2012) · Topics in organometallic chemistry · doi:10.1007/978-3-642-28288-1 · Cited by 16 · see citing works

Flagged first, then by citations

Research works printed but not linked: 40

R. T. Mathers and M. A. R. Meier, Wiley-VCH, 2011, pp. 9-27.
L. Montero de Espinosa and M. A. R. Meier, Eur. Polym. J., 2011, 47, 837-852.
A. Gandini and T. M. Lacerda, Prog. Polym. Sci., 2015, 48, 1- 39.
Y. Zhu, C. Romain and C. K. Williams, Nature, 2016, 540, 354-362.
H. Tsuji, in Bio-Based Plastics: Materials and Applications, ed. S. Kabasci, John Wiley & Sons, Ltd, 2014, pp. 171-239.
M. Rose and R. Palkovits, ChemSusChem, 2012, 5, 167-176.
E. Zakharova, A. Martínez de Ilarduya, S. León and S. Muñoz-Guerra, Des. Monomers Polym., 2017, 20, 157-166.
R. T. Mathers and M. A. R. Meier, Wiley-VCH, 2011, pp. 29-56.
G. Z. Papageorgiou, D. G. Papageorgiou, Z. Terzopoulou and D. N. Bikiaris, Eur. Polym. J., 2016, 83, 202-229.
G. L. Gregory, E. M. López-Vidal and A. Buchard, Chem. Commun., 2017, 53, 2198-2217.
X. Chen and R. A. Gross, Macromolecules, 1999, 32, 308- 314.
Y. Shen, X. Chen and R. A. Gross, Macromolecules, 1999, 32, 2799-2802.
Y. Shen, X. Chen and R. A. Gross, Macromolecules, 1999, 32, 3891-3897.
R. Kumar, W. Gao and R. A. Gross, Macromolecules, 2002, 35, 6835-6844.
K. Mikami, A. T. Lonnecker, T. P. Gustafson, N. F. Zinnel, P.-J. Pai, D. H. Russell and K. L. Wooley, J. Am. Chem. Soc., 2013, 135, 6826-6829.
A. T. Lonnecker, Y. H. Lim and K. L. Wooley, ACS Macro Lett., 2017, 6, 748-753.
S. E. Felder, M. J. Redding, A. Noel, S. M. Grayson and K. L. Wooley, Macromolecules, 2018, 51, 1787-1797.
Y. Song, X. Ji, M. Dong, R. Li, Y.-N. Lin, H. Wang and K. L. Wooley, J. Am. Chem. Soc., 2018, 140, 16053-16057.
G. L. Gregory, L. M. Jenisch, B. Charles, G. Kociok-Köhn and A. Buchard, Macromolecules, 2016, 49, 7165-7169.
G. L. Gregory, E. M. Hierons, G. Kociok-Köhn, R. I. Sharma and A. Buchard, Polym. Chem., 2017, 8, 1714-1721.
G. L. Gregory, G. Kociok-Köhn and A. Buchard, Polym. Chem., 2017, 8, 2093-2104.
Y.-Y. T. Tsao and K. L. Wooley, J. Am. Chem. Soc., 2017, 139, 5467-5473.
Y.-Y. T. Tsao, T. H. Smith and K. L. Wooley, ACS Macro Lett., 2018, 7, 153-158.
E. L. Dane and M. W. Grinstaff, J. Am. Chem. Soc., 2012, 134, 16255-16264.
S. L. Chin, Q. Lu, E. L. Dane, L. Dominguez, C. J. McKnight, J. E. Straub and M. W. Grinstaff, J. Am. Chem. Soc., 2016, 138, 6532-6540.
R. Xiao, E. L. Dane, J. Zeng, C. J. McKnight and M. W. Grinstaff, J. Am. Chem. Soc., 2017, 139, 14217-14223.
R. Xiao, J. Zeng and M. W. Grinstaff, ACS Macro Lett., 2018, 7, 772-777.
M. W. Grinstaff, A. S. Balijepalli, R. C. Sabatelle, M. Chen and B. Suki, Angew. Chem., Int. Ed., 2020, 59, 704-710.
P. A. Fokou and M. A. R. Meier, J. Am. Chem. Soc., 2009, 131, 1664-1665.
W. C. Shearouse, L. M. Lillie, T. M. Reineke and W. B. Tolman, ACS Macro Lett., 2015, 4, 284-288.
L. M. Lillie, W. B. Tolman and T. M. Reineke, Polym. Chem., 2017, 8, 3746-3754.
G. Hibert, E. Grau, D. Pintori, S. Lecommandoux and H. Cramail, Polym. Chem., 2017, 8, 3731-3739.
W. Gao, R. Hagver, V. Shah, W. C. Xie, R. A. Gross, M. F. Ilker, C. Bell, K. A. Burke and E. B. Coughlin, Macromolecules, 2007, 40, 145-147.
E. Zini, M. Gazzano, M. Scandola, S. R. Wallner and R. A. Gross, Macromolecules, 2008, 41, 7463-7468.
Y. Peng, J. Decatur, M. A. R. Meier and R. A. Gross, Macromolecules, 2013, 46, 3293-3300.
Y. Peng, D. J. Munoz-Pinto, M. Chen, J. Decatur, M. Hahn and R. A. Gross, Biomacromolecules, 2014, 15, 4214-4227.
T. Debsharma, F. N. Behrendt, A. Laschewsky and H. Schlaad, Angew. Chem., 2019, 131, 6790-6793.
J. J. Gallagher, M. A. Hillmyer and T. M. Reineke, ACS Sustainable Chem. Eng., 2015, 3, 662-667.
E. F. V. Scriven, Chem. Soc. Rev., 1983, 12, 129-161.
A. Rybak and M. A. R. Meier, ChemSusChem, 2008, 1, 542- 547.

Sorted by citations

Control of Crystallinity and Stereocomplexation of Synthetic Carbohydrate Polymers from <scp>d</scp>‐ and <scp>l</scp>‐Xylose
McGuire, T. M., Bowles, J., Deane, E., Farrar, E. H. E., Grayson, M. N., & Buchard, A. (2021) · Angewandte Chemie International Edition · doi:10.1002/anie.202013562 · Cited by 55 · see citing works
Self-citation
Master of Chaos and Order: Opposite Microstructures of PCL‐co‐PGA‐co‐PLA Accessible by a Single Catalyst**
Rittinghaus, R. D., Zenner, J., Pich, A., Kol, M., & Herres‐Pawlis, S. (2022) · Angewandte Chemie International Edition · doi:10.1002/anie.202112853 · Cited by 32 · see citing works

Authors: Piccini, M., Leak, D. J., Chuck, C. J., & Buchard, A.
Affiliations: University of Bath (GB)
Corresponding author: Buchard, Antoine
ORCID: Piccini, Marco
Leak, David J.
Chuck, Christopher J.
Buchard, Antoine
Venue: Polymer Chemistry
Publisher: Royal Society of Chemistry (RSC)
Published: 2020
Volume: 11
Issue: 15
Pages: 2681-2691
ISSN: 1759-9954 (ISSN-L)
1759-9962
DOI: 10.1039/c9py01809c
OpenAlex: W3011179685
Cited by: 55
References: 42
Citations by year: 2026: 6 · 2025: 11 · 2024: 6 · 2023: 11 · 2022: 12 · 2021: 5 · 2020: 4
FWCI: 2.08
Type: journal article
Language: en
Open access: hybrid
doi.org
Licence: cc-by
creativecommons.org/licenses/by/3.0/ (vor, 72 d)
Locations: Polymer Chemistry (publishedVersion, cc-by)
Funders: Engineering and Physical Sciences Research Council (EP/L016354/1)
Royal Society (UF/160021 fellowship)
Topics: Physical Sciences › Materials Science › Biomaterials › biodegradable polymer synthesis and properties
Physical Sciences › Materials Science › Polymers and Plastics › Polymer composites and self-healing
Physical Sciences › Engineering › Biomedical Engineering › Catalysis for Biomass Conversion
Keywords: hemicellulose sugars, D-xylose, D-mannose, castor oil, unsaturated fatty acids, transparent films, bio-based polymers

About these checks

Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.

Statistics and arithmetic are recomputed, not judged.

Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.

What counts as a claim ›How we measure confidence ›How we check this ›

Are you an author, or do you see a problem with this page? Request a review

Polymers from sugars and unsaturated fatty acids: ADMET polymerisation of monomers derived from d -xylose, d -mannose and castor oil

Abstract

Integrity signals

Claims the paper makes

Claims other papers make about this one

Self-check

Cites

Cited by

Related

Record

About these checks