Heterograft copolymers of poly(ε‐caprolactone) prepared by combination of ATRA “grafting onto” and ATRP “grafting from” processes
Abstract
This paper aims at reporting on the synthesis of a heterograft copolymer by combining the “grafting onto” process based on atom transfer radical addition (ATRA) and the “grafting from” process by atom transfer radical polymerization (ATRP). The statistical copolymerization of ε‐caprolactone (εCL) and α‐chloro‐ε‐caprolactone (αClεCL) was initiated by 2,2‐dibutyl‐2‐stanna‐1,3‐dioxepane (DSDOP), followed by ATRA of parts of the chlorinated units of poly(αClεCL‐co‐εCL) on the terminal double bond of α‐MeO,ω‐CH 2CHCH 2CO 2‐poly(ethylene oxide) (PEO). The amphiphilic poly(εCL‐g‐EO) graft copolymer collected at this stage forms micelles as supported by dynamic light scattering (DLS) and transmission electron microscopy (TEM). The unreacted pendant chloro groups of poly(εCL‐g‐EO) were used to initiate the ATRP of styrene with formation of copolymer with two populations of randomly distributed grafts, that is PEO and polystyrene. © 2006 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 44: 6015–6024, 2006
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With vinyl acetic acid as olefin, not all chlorinated units are reduced and consequently no ATRA occurs.
“The situation is even worst when vinyl acetic acid is substituted for 3-buten-1-ol.With this olefin, no all the chlorinated units are reduced and consequently no ATRA occurs.”
From Recent advances in the synthesis of aliphatic polyesters by ring-opening polymerization☆ (2008) · cites this paper as [149]
18 chlorinated units per chain are lost by reduction during ATRA.
“However, 18 chlorinated units per chain are lost by reduction during ATRA.”
From Recent advances in the synthesis of aliphatic polyesters by ring-opening polymerization☆ (2008) · cites this paper as [149]
Reducing activity of catalyst (HMTETA instead of Me6TREN) leads to ATRA with a moderate yield of 32% after 24 h.
“This problem was solved by reducing the activity of the catalyst (HMTETA is used instead of Me 6 TREN) leading to ATRA with a moderate yield of 32% after 24 h.”
From Recent advances in the synthesis of aliphatic polyesters by ring-opening polymerization☆ (2008) · cites this paper as [149]
ATRA of α-methoxy, ω-acrylate-PEO (Mn PEO=750) onto poly(αClεCL-co-εCL) (Mn=17,500; 48 αClεCL units) yields a graft copolymer, with 9 PEO grafts.
“Moreover, ATRA of commercially available α-methoxy, ω-acrylate-PEO (Mn (PEO = 750) onto poly(αClεCL-co-εCL) (Mn= 17,500 ; 48 αClεCL units) yields a graft copolymer, with 9 PEO grafts [149].”
From Recent advances in the synthesis of aliphatic polyesters by ring-opening polymerization☆ (2008) · cites this paper as [149]
α-chlorocyclohexanone is easily converted into parent lactone (αClεCL) by one-step oxidation with m-CPBA with high yield, the chlorine atom of the lactone being activated by proximity of the ester group.
“α-chlorocyclohexanone is easily converted into the parent lactone (αClεCL) by one-step oxidation with m-CPBA with high yield, the chlorine atom of the lactone being activated by the proximity of the ester group (Scheme 15) [148,149].”
From Recent advances in the synthesis of aliphatic polyesters by ring-opening polymerization☆ (2008) · cites this paper as [149]
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- Authors
- Riva, R., Rieger, J., Jérôme, R., & Lecomte, P.
- Affiliations
- University of Liège (BE)
- Corresponding author
- Jérôme, R.
- ORCID
- Venue
- Journal of Polymer Science Part A: Polymer Chemistry
- Publisher
- Wiley
- Published
- 2006-09-12
- Volume
- 44
- Issue
- 20
- Pages
- 6015-6024
- ISSN
- 0887-624X (ISSN-L)
- 1099-0518
- OpenAlex
- W2013926801
- Cited by
- 48
- References
- 25
- Citations by year
- 2024: 1 · 2023: 1 · 2022: 1 · 2019: 2 · 2017: 2 · 2016: 2 · 2015: 2 · 2014: 3 · 2013: 1 · 2012: 10
- FWCI
- 3.41
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Journal of Polymer Science Part A Polymer Chemistry (publishedVersion)
- Open Repository and Bibliography (University of Liège) (submittedVersion)
- Topics
- Physical Sciences › Chemistry › Organic Chemistry › Advanced Polymer Synthesis and Characterization
- Physical Sciences › Materials Science › Biomaterials › biodegradable polymer synthesis and properties
- Physical Sciences › Materials Science › Polymers and Plastics › Polymer Synthesis and Characterization
- Keywords
- polycaprolactone, atom transfer radical addition, atom transfer radical polymerization, grafting onto, grafting from, poly(ethylene oxide), amphiphilic copolymers, micelles, polystyrene
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