Journal ArticleDOI
Guanidine and Amidine Organocatalysts for Ring-Opening Polymerization of Cyclic Esters
Bas G. G. Lohmeijer,Russell C. Pratt,Frank A. Leibfarth,John W. Logan,David A. Long,Andrew P. Dove,Fredrik Nederberg,Jeongsoo Choi,Charles G. Wade,Robert M. Waymouth,James L. Hedrick +10 more
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TLDR
In this article, the ring-opening polymerization (ROP) of cyclic esters such as lactide (LA), δ-valerolactone (VL), and e-caprolactone(CL) was achieved.Abstract:
1,5,7-Triazabicyclo[4.4.0]dec-5-ene (TBD), N-methyl-TBD (MTBD), and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) are effective organocatalysts for the ring-opening polymerization (ROP) of cyclic esters such as lactide (LA), δ-valerolactone (VL), and e-caprolactone (CL). TBD is shown to polymerize LA, VL, and CL in a fast and controlled manner, whereas MTBD and DBU polymerized LA and addition of a thiourea cocatalyst led to the ROP of VL and CL being achieved. Each of the catalysts produced polymers displaying high end group fidelity, good correlation between theoretical and observed molecular weight, and linear relationships between conversion and molecular weight. The enhanced activity of TBD relative to MTBD and DBU is attributed to its bifunctionality, enabling the simultaneous activation of both the cyclic ester monomer and the alcohol group of the initiator/propagating species. Temperature-dependent NMR studies generated individual association constants for MTBD with benzyl alcohol and thiourea with VL. ...read more
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Journal ArticleDOI
Polymerization of trimethylene carbonates using organic phosphoric acids
Jiaqi Liu,Saide Cui,Zhenjiang Li,Songquan Xu,Jiaxi Xu,Pan Xianfu,Liu Yaya,He Dong,Herui Sun,Kai Guo +9 more
TL;DR: In this article, the homopolymerization of trimethylene carbonates (TMC) and their diblock copolymerization to PTMC-b-PVL and PTMCb-PCL were carried out using benzyl alcohol (BnOH) as the initiator and 1,1′-binaphthyl-2,2′-diyl hydrogen phosphate (BNPH) as a catalyst in toluene at room temperature.
Journal ArticleDOI
Organocatalytic Copolymerization of a Cyclic Carbonate Bearing Protected 2,2-bis(hydroxymethyl) Groups and d,l-lactide. Effect of Hydrophobic Block Chemistry on Nanoparticle Properties
Yanet Elised Aguirre-Chagala,Yanet Elised Aguirre-Chagala,José Luís Guedes dos Santos,Rafael Herrera-Nájera,Margarita Herrera-Alonso +4 more
TL;DR: In this paper, the organocatalytic copolymerization of a derivative of trimethylene carbonate bearing protected 1,3-diols and d,l-lactide was studied.
Journal ArticleDOI
Synthesis of ferrocene-functionalized monomers for biodegradable polymer formation
Brianna M. Upton,Raymond M. Gipson,Selma Duhović,Brian R. Lydon,Nicholas M. Matsumoto,Heather D. Maynard,Paula L. Diaconescu +6 more
TL;DR: In this article, cyclic carbonate and δ-valerolactone substrates functionalized with ferrocene were synthesized via alkyne-azide "click" cycloaddition.
Patent
Polymer and method for producing the same
Taichi Nemoto,Nobuyuki Mase,Takeshi Sako,Idzumi Okajima,Shunsuke Mori,Chiaki Tanaka,Yoshitaka Yamauchi,Jyun Ishiduka +7 more
TL;DR: In this paper, a method for polymerizing a ring-opening polymerizable monomer in a compressive fluid with a metal-free organic catalyst to produce a polymer is described.
Journal ArticleDOI
Direct ring-opening of lactide with amines: application to the organo-catalyzed preparation of amide end-capped PLA and to the removal of residual lactide from PLA samples
Aurélie Alba,Aurélie Alba,Olivier Thillaye du Boullay,Olivier Thillaye du Boullay,Blanca Martin-Vaca,Blanca Martin-Vaca,Didier Bourissou,Didier Bourissou +7 more
TL;DR: In this paper, a two-step one-pot strategy was developed in which primary or secondary amines were reacted with an excess of lactide prior to the addition of the ROP catalyst, DBU.
References
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Journal ArticleDOI
Controlled ring-opening polymerization of lactide and glycolide.
TL;DR: This work focuses on the characterization of the phytochemical components of Lactide ROP and their role in the regulation of cell reprograming.
Journal ArticleDOI
Polymerization of Lactide with Zinc and Magnesium β-Diiminate Complexes: Stereocontrol and Mechanism
Bradley M. Chamberlain,Ming Cheng,David Roger Moore,Tina M. Ovitt,Emil B. Lobkovsky,Geoffrey W. Coates +5 more
TL;DR: The substituents on the beta-diiminate ligand exert a significant influence upon the course of the polymerizations, affecting both the degree of stereoselectivity and the rate of polymerization.
Journal ArticleDOI
A review of biodegradable polymers: uses, current developments in the synthesis and characterization of biodegradable polyesters, blends of biodegradable polymers and recent advances in biodegradation studies
TL;DR: A review of the uses of biodegradable polymers in terms of their relevance within current plastic waste management of packaging materials, biomedical applications and other uses is presented in this paper.
Journal ArticleDOI
Extension of the self-consistent spectrophotometric basicity scale in acetonitrile to a full span of 28 pKa units: unification of different basicity scales.
Ivari Kaljurand,Agnes Kütt,Lilli Sooväli,Toomas Rodima,Vahur Mäemets,and Ivo Leito,Ilmar A. Koppel +6 more
TL;DR: The earlier compiled self-consistent spectrophotometric basicity scale in acetonitrile (AN) was expanded to range from 3.8 to 32.0 pK(a) units, that is 28 orders of magnitude, and 54 new relative basicity measurements were carried out and 37 new compounds were introduced to the scale.
Journal ArticleDOI
Stereochemistry of Lactide Polymerization with Chiral Catalysts: New Opportunities for Stereocontrol Using Polymer Exchange Mechanisms
Tina M. Ovitt,Geoffrey W. Coates +1 more
TL;DR: A polymer exchange mechanism is proposed to account for the PLA microstructures resulting from rac-4, which polymerizes meso-lactide to syndiotactic poly(lactic acid) (PLA) and heterotactic and isotactic stereoblock PLA, respectively.