A Novel Synthetic Approach to Networked Polymers without Volume Shrinkage on Cross-Linking Polymerization:  Cationic Copolymerization of a Monofunctional Epoxide and a Spiro Orthocarbonate Bearing Norbornene Backbone

Hino, Taro; Endō, Takeshi

doi:10.1021/ma030136s

Cited by 45 publications

(35 citation statements)

References 7 publications

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“…Norbornene can be commonly polymerized by three different mechanisms: ring-opening metathesis polymerization (ROMP), 39 cationic polymerization, 40 and vinyl addition polymerization. [41][42][43][44] Among these polymerization mechanisms, vinyl polymerized norbornene copolymers are Scheme I. Schematic on the preparation of luminescent PNB/QD composite nanorods.…”

Section: Resultsmentioning

confidence: 99%

Luminescent polynorbornene/quantum dot composite nanorods and nanotubes prepared from AAO membrane templates

Cho

Char

2009

Macromol. Res.

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Luminescent polynorbornene (PNB)/quantum dot (CdSe@ZnS; QD) composite nanorods and nanotubes were successfully prepared using anodic aluminum oxide (AAO) membranes of various pore sizes as templates. To protect QDs with high quantum yield from quenching during the phosphoric acid treatment used to remove the AAO templates, chemically stable and optically clear norbornene-maleic anhydride copolymers (P(NB-r-MA)) were employed as a capping agent for QDs. The amine-terminated QDs reacted with maleic anhydride moieties in P(NBr-MA) to form PNB-grafted QDs. The chemical-and photo-stability of QDs encapsulated with PNB copolymers were investigated by photoluminescence (PL) spectroscopy. By varying the pore size of the AAO templates from 40 to 380 nm, PNB/QD composite nanorods or nanotubes were obtained with a good dispersion of QDs in the PNB matrix.

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Section: Resultsmentioning

confidence: 99%

Luminescent polynorbornene/quantum dot composite nanorods and nanotubes prepared from AAO membrane templates

Cho

Char

2009

Macromol. Res.

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“…Renewed interest has arisen in the development of new spiro orthocarbonates (SOCs) because these monomers undergo double ring‐opening polymerization that may result in volume expansion 1–3. SOCs are two‐ring compounds with the central carbon atom connected to four oxygen atoms.…”

Section: Introductionmentioning

confidence: 99%

Novel diol spiro orthocarbonates derived from glycerol as anti‐shrinkage additives for the cationic photopolymerization of epoxy monomers

Ortiz

Duarte

Gómez

et al. 2010

Polymer International

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Shrinkage that takes place during polymerizations induces internal stress in polymeric materials generating a series of problems like poor adhesion to substrates and delamination in coatings or microcracks and microvoids in composites. Some additives like spiro orthocarbonates can reduce or eliminate this shrinkage. This paper deals with the synthesis of novel diol spiro orthocarbonates (DIOL SOCs) and their effect as anti‐shrinkage additives in the photopolymerization of the monomer 3,4‐epoxycyclohexyl‐3′, 4′‐epoxycyclohexanecarboxylate. It was found that increasing the concentration of the DIOL SOCs resulted in higher conversion of the monomer due to the presence of hydroxyl groups. The viscoelastic properties of the polymer products were also measured. It was observed that at 5 mol% of the mixture of DIOL SOCs there was an increase in the storage modulus due to the crosslinking produced by the bifunctional SOCs. However, at higher concentrations, a decrease in the storage modulus was observed. The level of shrinkage using the DIOL SOCs at 20 mol% was reduced by 45% when compared to the case without any additive. DIOL SOCs can be easily prepared by reacting glycerol with tetraethylorthocarbonate. These additives reduced significantly the level of shrinkage of the polyether derived from the diepoxycyclohexane monomer. Copyright © 2010 Society of Chemical Industry

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“…Some kinds of bicyclic monomers such as spiroorthoesters (SOEs), spiroorthocarbonates (SOCs) and bicycloorthoesters (BOEs) have been reported to maintain their volume or actually expand during the double ring-opening polymerization. [7][8][9][10] SOEs can be readily synthesized from epoxides and lactones [11,12] and undergo cationic…”

Section: Introductionmentioning

confidence: 99%

Microwave‐Accelerated Polymerization of 2‐Phenoxymethyl‐1,4,6‐trioxaspiro[4,4]nonane with Diglycidyl Ether of Bisphenol A

Canadell¹,

Mantecón²,

Cádiz³

2007

Macro Chemistry & Physics

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The cationic copolymerization of 2‐phenoxymethyl‐1,4,6‐trioxaspiro[4,4]nonane with DGEBA under microwave irradiation using ytterbium and lanthanum triflates as initiators is described. A comparison with thermal heating showed a great enhancement in the reaction rates and a higher SOE incorporation in the network. The double ring opening of SOE reduces the usual shrinkage of epoxy resins on curing, and it was lower under microwave irradiation. Moreover, the ytterbium triflate initiator lead to a higher incorporation of linear ester moieties in the network than lanthanum triflate.

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A Novel Synthetic Approach to Networked Polymers without Volume Shrinkage on Cross-Linking Polymerization: Cationic Copolymerization of a Monofunctional Epoxide and a Spiro Orthocarbonate Bearing Norbornene Backbone

Cited by 45 publications

References 7 publications

Luminescent polynorbornene/quantum dot composite nanorods and nanotubes prepared from AAO membrane templates

Luminescent polynorbornene/quantum dot composite nanorods and nanotubes prepared from AAO membrane templates

Novel diol spiro orthocarbonates derived from glycerol as anti‐shrinkage additives for the cationic photopolymerization of epoxy monomers

Microwave‐Accelerated Polymerization of 2‐Phenoxymethyl‐1,4,6‐trioxaspiro[4,4]nonane with Diglycidyl Ether of Bisphenol A

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