Synthesis of polymers with hydroxyl end groups by atom transfer radical polymerization

Coessens, Veerle; Matyjaszewski, Krzysztof

doi:10.1002/(sici)1521-3927(19990301)20:3<127::aid-marc127>3.3.co;2-u

Cited by 35 publications

(66 citation statements)

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“…Compared to living ionic polymerization techniques, ATRP shows insensitivity to water or other protic species,54, 55 high versatility in terms of monomer eligibility46 and access to well‐defined end‐functional polymers56, 57 or macromonomers 58–60. First efforts employing controlled radical polymerization in continuous flow were made by Zhu et al who successfully developed a column reactor with supported CuBr‐HMTETA catalyst for the homogeneous bulk ATRP of methyl methacrylate 61.…”

Section: Radical Polymerizationsmentioning

confidence: 99%

Microstructured Reactors for Polymer Synthesis: A Renaissance of Continuous Flow Processes for Tailor‐Made Macromolecules?

Wilms

Klos

Frey

2008

Macro Chemistry & Physics

119

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Organic synthesis in microfluidic devices has attracted increasing interest in recent years. However, little efforts had been undertaken to exploit this novel technology for polymer chemistry until several recent studies demonstrated the interesting potential of microreactors for the synthesis and modification of polymers. In fact, anionic polymerizations in continuous capillary flow‐tube systems were established already in 1962 in pioneering work by Szwarc. Subsequent work focused on detailed kinetic analyses in such reactors. The present article explores different current strategies developed by several research groups to realize bulk and solution polymerizations using continuous flow microreactors. Inherent benefits and limitations of these systems compared to traditional laboratory set‐ups are discussed. We present a variety of recent pioneering and advanced approaches to realize free radical, controlled radical, cationic and anionic polymerizations in microtechnological reaction devices. In some cases, surprisingly narrow molecular weight distributions have been obtained, demonstrating the promising potential of this approach for the tailoring of polymer structures.

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Section: Radical Polymerizationsmentioning

confidence: 99%

Microstructured Reactors for Polymer Synthesis: A Renaissance of Continuous Flow Processes for Tailor‐Made Macromolecules?

Wilms

Klos

Frey

2008

Macro Chemistry & Physics

119

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“…Water traces in the chain extender were completely removed before its use by heating at 60 °C under vacuum for 5 h. Various α , α ′ ‐dihydroxyl‐poly(butyl acrylate)s (PBA(OH) 2 ) were prepared by atom transfer radical polymerization (ATRP) with CuBr/PMDETA ( N , N , N′ , N′ , N″ ‐pentamethyldiethylenetriamine) as a catalytic system according to ref. 12 and ref. 13 In this study, the experiments were carried out with PBA(OH) 2 with a molar mass of 2 500 g · mol −1 (measured using 1 H NMR) and a commercial PCL with a molar mass of 4 000 g · mol −1 .…”

Section: Experimental Partmentioning

confidence: 94%

Relationship Between Architecture and Adhesion in Polyurethane‐Based Copolymers, 2

Baron

Rodríguez‐Hernández

Papon

2005

Macro Chemistry & Physics

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Summary: This study describes the chain extension, with polycaprolactone diols, of polyurethane‐graft‐poly(butyl acrylate)s which were first prepared by the step growth polymerization of a mixture of diphenylmethane‐4,4′‐diisocyanate (MDI) and α,α′‐dihydroxyl‐poly(butyl acrylate)s. The success of the chain extension reaction was studied and confirmed by 1H NMR, SEC and DSC analysis. The incorporation of polycaprolactone sequences in the polyurethane chains modified their specific adhesive properties, bringing cohesion to the material, as demonstrated by tack measurements.

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“…[8][9][10] The halogen atom, considered as harmful to the environment, has been replaced through different standard organic procedures such as nucleophilic substitution, free-radical chemistry, or electrophilic addition, [8] which allows polymers with, for example, hydroxy, [11] phosphonium, [12] allyl, [13,14] or other specific [15,16] end groups to be obtained. These last functions make these polymers reactive for the synthesis of graft or block copolymers, for example.…”

Section: Communicationmentioning

confidence: 99%

A New Route for the Modification of Halogen End Groups to Amino End‐Functionalized Poly(tert‐butyl acrylate)s

Monge

Giani

Ruiz

et al. 2007

Macromol. Rapid Commun.

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The synthesis of primary amine end‐functional poly(tert‐butyl acrylate)s has been achieved by using the Gabriel reaction. Polymerization of tert‐butyl acrylate was first achieved by atom transfer radical polymerization using ethyl‐2‐bromoisobutyrate or paramethoxyphenyl‐2‐bromoisobutyrate as initiator. Both resulting polymers, with a bromide‐end atom, were converted into phthalimido intermediates which then were successfully hydrolyzed using potassium hydroxide in tert‐butyl alcohol to result in poly(tert‐butyl acrylate)s terminated by a primary amine function. End group interconversions were followed by 1H NMR, FT‐IR, and MALDI‐TOF MS measurements. All the results proved that quantitative transformations were achieved at each step. Moreover, the method developed is very easy to carry out.magnified image

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Synthesis of polymers with hydroxyl end groups by atom transfer radical polymerization

Cited by 35 publications

References 0 publications

Microstructured Reactors for Polymer Synthesis: A Renaissance of Continuous Flow Processes for Tailor‐Made Macromolecules?

Microstructured Reactors for Polymer Synthesis: A Renaissance of Continuous Flow Processes for Tailor‐Made Macromolecules?

Relationship Between Architecture and Adhesion in Polyurethane‐Based Copolymers, 2

A New Route for the Modification of Halogen End Groups to Amino End‐Functionalized Poly(tert‐butyl acrylate)s

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