PDMS‐Containing Alternating Copolymers Obtained by Click Polymerization

Bretzler, Victor; Grübel, Matthias; Meister, Simon; Rieger, Bernhard

doi:10.1002/macp.201400178

Cited by 17 publications

(9 citation statements)

References 40 publications

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“…We noticed examples of successful application of click chemistry methods using PDMS polymer matrices − and decided to combine these functions with traditional reactions for synthesizing functional PDMS-oligomers and use the resulting oligomers to obtain carboxyl-containing PDMSs that have rich prospects for application in various technical fields. − …”

Section: Introductionmentioning

confidence: 99%

Acid-Catalyzed Rearrangement of Azidopropyl-Siloxane Monomers for the Synthesis of Azidopropyl-Polydimethylsiloxane and Their Carboxylic Acid Derivatives

et al. 2021

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In this work, we were the first to show the possibility of synthesizing polydimethylsiloxanes (PDMSs) with azidopropyl-functional groups at the silicon atom by the classical methods for PDMS synthesis, that is, ring-opening polymerization (ROP) and catalytic rearrangement of siloxanes in the presence of a strong acid (CF3SO3H). The suggested method was used to obtain PDMSs containing azidopropyl-functional groups at both ends of the polymer chain (telechelics) as well as PDMSs with irregular structures containing different fractions (5–50%) of azidopropyl-functional groups in the main polymer chain. The suggested method also proved to be efficient for synthesizing PDMSs containing both azidopropyl- and hydridosilyl-functional groups simultaneously. As a result, PDMSs with different mutual arrangements of two types of functional groups along the PDMS chain were obtained. The method for the catalytic rearrangement of low-molecular-weight siloxanes that we used made it possible to obtain azidopropyl-functional PDMSs in a wide range of molecular weights from 2000 to 88,000 according to gel permeation chromatography (GPC) data. The possibility of further modification of the resulting azidopropyl-functional PDMS, as well as multifunctional PDMSs containing azidopropyl- and hydridosilyl-functional groups simultaneously, by azide-alkyne cycloaddition reactions was demonstrated. The polymers obtained were characterized by 1H and 29Si NMR spectroscopy and by GPC.

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Section: Introductionmentioning

confidence: 99%

Acid-Catalyzed Rearrangement of Azidopropyl-Siloxane Monomers for the Synthesis of Azidopropyl-Polydimethylsiloxane and Their Carboxylic Acid Derivatives

et al. 2021

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“…Besides the merits inherited from multicomponent reactions (MCRs), such as high atom economy, step effectiveness, environmental benefits, simple and inexpensive reactants, operational simplicity and synthetic efficiency, such MCPs compared to other polymerizations is the great structural diversity of the products that could be obtained through various combinations of multiple monomers. 21,22 Most importantly, instead of only linking functional monomeric units together in a polymer chain, MCPs could build new functional units embedded in the main chains of polymers directly. With these advantages, MCPs could perform as a powerful tool for the development of functional polymer materials with great efficiency and synthetic simplicity.…”

Section: Introductionmentioning

confidence: 99%

Multicomponent Cyclopolymerization of Alkynes, Isocyanides and Isocyanates Toward Heterocyclic Polymers

Wang¹,

Li²,

Peng³

et al. 2021

Preprint

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Multicomponent cyclopolymerization (MCCP) based on isocyanides, among the tremendous synthetic methodologies, is a powerful tool for the preparation of functional heterocyclic polymers like poly(maleimide)s (PMDs), which should be further developed. In this work, an atom-economic and catalyst-free MCCP of activated alkynes, diisocyanides and diisocyanates was fully explored. The PMDs with high weight-average molecular weights (Mw up to 29 000) were facilely produced in satisfactory yields (up to 85%). The resultant polymers showed excellent solubility, high thermal stability, and good film-forming ability, and their thin films possessed high refraction indices (RI) in a range of 1.613 to 1.708 at 632.8 nm. Therefore, this work not only supplements the isocyanide-based multicomponent cyclopolymerizations but also enriches the family of polymerization reactions based on triple-bond building blocks.

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“…Schmidt et al combined organic dialkynes and oligo (siloxanes) to develop telechelic polymers having thermoplastic elastomeric characteristics, through click chemistry . Bretzler et al established the structure‐property relationship of PDMS‐containing alternating copolymers obtained by click reaction . Terminal cross‐linking of the chemically tuned telechelic polymers can be utilized as means to prepare membranes and elastomers for various applications.…”

Section: Introductionmentioning

confidence: 99%

Azide telechelics chain extended by click reaction: Synthesis, characterization, and cross‐linking

Sunitha

Unnikrishnan

Nair

2018

Polymers for Advanced Techs

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Azide telechelics of poly(dimethylsiloxane) (PDMS), polypropylene oxide (PPO), and polyethylene oxide (PEO) were synthesized from the corresponding epoxy telechelics and characterized. These oligomeric azides were chain extended by reaction with bispropargyl ether of bisphenol A (BPEBA) through a copper-catalyzed azide-alkyne cycloaddition (CuAAC) reaction. PDMS manifested a faster reaction in contrast to PPO or PEO. The chain-extended polymers underwent cross-linking above 170°C through thermal cleavage of residual (terminal) azide groups. This was manifested in their rheograms and was further substantiated by FTIR and NMR spectroscopic analyses. Dynamic mechanical analyses of the cross-linked polymers exhibited characteristic transitions of hard and soft segments, implying microphase separation in the system. Microscopic evaluation of the thermally cross-linked sample revealed a porous morphology with microsized to nanosized pores. KEYWORDS azide telechelics, propargyl ether, thermal cross-linking, triazole, click reaction 1 | INTRODUCTION Telechelic polymers evince a lot of interest because of their various applications such as precursors for the synthesis of multiblock copolymers and synthesis aid for a large number of branched and complex polymeric structures. 1,2 For example, hydroxyl-terminated polybutadiene (HTPB) is a well-known telechelic system used as a propellant binder and as adhesive, sealant, elastomer, 3 etc. End-functional poly(dimethylsiloxane) (PDMS) is another example of a very useful synthesis intermediate widely used in adhesives, sealants, and coatings formulations 4 in space research. The possibility to externally steer the morphology and the associated physical properties of telechelic polymers renders them important and versatile building blocks for modern materials science. 2,3Diverse methods such as anionic, cationic, ring opening, group transfer, free radical, step-growth polymerization, and chain scission processes are adopted for the syntheses of these telechelic polymers. [5][6][7][8] The criticality in synthesis of telechelic polymers lies in the quantitative introduction and subsequent conversion of the functional group at the chain ends. Living polymerization technique is a good technique for getting telechelic polymers with narrow molecular weight distribution. 9,10 However, the properties of polymers obtained by end-linking of telechelic oligomers depend strongly on stoichiometry, side reactions, extent of conversion, etc. The relative reactivities of the groups, substitution effects, side groups, etc play a major role 11,12 in deciding the success factor. Different types of synthesis strategies such as Diels-Alder, [13][14][15] thiol-ene, [16][17][18][19] and azide-alkyne 20,21 figure under the title of "click chemistry." Of these, the Diels-Alder belongs to a class of thermoreversible reactions. 22 Copper-catalyzed azide-alkyne cyclo addition (CuAAC) is shown to be the most effective and versatile, since it is highly specific and efficient, requires mild conditions, 23 has ...

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PDMS‐Containing Alternating Copolymers Obtained by Click Polymerization

Cited by 17 publications

References 40 publications

Acid-Catalyzed Rearrangement of Azidopropyl-Siloxane Monomers for the Synthesis of Azidopropyl-Polydimethylsiloxane and Their Carboxylic Acid Derivatives

Acid-Catalyzed Rearrangement of Azidopropyl-Siloxane Monomers for the Synthesis of Azidopropyl-Polydimethylsiloxane and Their Carboxylic Acid Derivatives

Multicomponent Cyclopolymerization of Alkynes, Isocyanides and Isocyanates Toward Heterocyclic Polymers

Azide telechelics chain extended by click reaction: Synthesis, characterization, and cross‐linking

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