Cationic ring‐opening polymerization of six‐membered cyclic carbonates with ester groups

Nemoto, Nobukatsu; Sanda, Fumio; Endō, Takeshi

doi:10.1002/pola.1108

Cited by 23 publications

(27 citation statements)

References 26 publications

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“…A novel polystyrenebased low-density material with no shrinkage was synthesized and investigated. 88,89 The schematic concept is summarized in Fig. 5.…”

Section: E Polystyrene and Polyhipe (High Internal Phase Emulsion)mentioning

confidence: 99%

“…By contrast, cyclic carbonates and thiocarbonates undergo cationic and anionic ring opening polymerization resulting in volume expansion. [86][87][88] By combination of conventional free-radical polymerization and volume expansion ring opening polymerization, it would be possible to counteract the shrinkage with volume expansion during the polymerization process. A novel polystyrenebased low-density material with no shrinkage was synthesized and investigated.…”

Section: E Polystyrene and Polyhipe (High Internal Phase Emulsion)mentioning

confidence: 99%

“…In the second step, the linear PS-based copolymers are gelled by ring-opening polymerization of the pendant cyclic moiety resulting in no volume change. For this purpose, two monomers 5-(4-vinylbenzyl) oxymethyl-5-methyl-1,3-dioxane-2-thione) 87 and 4-vinylphenyloxirane were synthesized, 88 and then used to synthesize polystyrene based copolymerization.…”

Section: E Polystyrene and Polyhipe (High Internal Phase Emulsion)mentioning

confidence: 99%

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A review of low density porous materials used in laser plasma experiments

2018

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This review describes and categorizes the synthesis and properties of low density porous materials, which are commonly referred to as foams and are utilized for laser plasma experiments. By focusing a high-power laser on a small target composed of these materials, high energy and density states can be produced. In the past decade or so, various new target fabrication techniques have been developed by many laboratories that use high energy lasers and consequently, many publications and reviews followed these developments. However, the emphasis so far has been on targets that did not utilize low density porous materials. This review therefore, attempts to redress this balance and endeavors to review low density materials used in laser plasma experiments in recent years. The emphasis of this review will be on aspects of low density materials that are of relevance to high energy laser plasma experiments. Aspects of low density materials such as densities, elemental compositions, macroscopic structures, nanostructures, and characterization of these materials will be covered. Also, there will be a brief mention of how these aspects affect the results in laser plasma experiments and the constrictions that these requirements put on the fabrication of low density materials relevant to this field. This review is written from the chemists' point of view to aid physicists and the new comers to this field.

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“…A novel polystyrenebased low-density material with no shrinkage was synthesized and investigated. 88,89 The schematic concept is summarized in Fig. 5.…”

Section: E Polystyrene and Polyhipe (High Internal Phase Emulsion)mentioning

confidence: 99%

Section: E Polystyrene and Polyhipe (High Internal Phase Emulsion)mentioning

confidence: 99%

Section: E Polystyrene and Polyhipe (High Internal Phase Emulsion)mentioning

confidence: 99%

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A review of low density porous materials used in laser plasma experiments

2018

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“…5‐Methyl‐5‐benzoyloxymethyl‐1,3‐dioxan‐2‐one (11) :30 Conditions: [ Al t Bu ]: 5 mol %; [PPNI]: 10 mol %; T : 110 °C, p (CO 2 ): 40 bar, time: 65 h; conversion: 80 %. Isolated by column chromatography (EtOAc/hexane 1:2 to 1:1 v/v) in 65 % yield.…”

Section: Methodsmentioning

confidence: 99%

Highly Chemoselective Catalytic Coupling of Substituted Oxetanes and Carbon Dioxide

Rintjema

Guo

Martín

et al. 2015

Chemistry A European J

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Abstract:The chemo--selective coupling of oxetanes and carbon dioxide to afford functional, heterocyclic organic compounds known as six--membered cyclic carbonates remains a challenging topic. Here we describe an effective method for their synthesis relying on the use of Al--catalysis. The catalytic reactions can be carried out with excellent selectivity for the cyclic carbonate product tolerating various (functional) groups present in the 2--and 3--position(s) of the oxetane ring, and the presented methodology is the first general approach towards the formation of six--membered cyclic carbonates (6MCCs) through oxetane/CO 2 coupling chemistry. Apart from a series of substituted six--membered cyclic carbonates, also the unprecedented room temperature coupling of oxetanes and CO 2 is disclosed giving, depending on the structural features of the substrate, a variety of five--and six--membered heterocyclic products. A mechanistic rationale is presented for their formation and support for the intermediary presence of a carbonic acid derivative is given. The presented functional carbonates may hold great promise as building blocks in organic synthesis and the development of new, biodegradable polymers.

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“…[5][6][7][8][9][10] Homopolymerization of sixand seven-membered cyclic carbonates (6CC and 7CC) have been reported before. [1,3,[11][12][13][14][15][16][17][18][19][20] A typical property of cyclic carbonates is their volume expansion during polymerization in contrast to the usual contracting monomers such as vinyl monomers; [21,22] therefore, the cyclic carbonates are regarded as versatile monomers from the viewpoint of precise molding. In the field of material science, the copolymerization of the cyclic carbonates with other monomers as a means of controlling volume shrinkage is an important application.…”

Section: Introductionmentioning

confidence: 99%

Cationic Copolymerization Behavior of Glycidyl Phenyl Ether with Seven‐Membered Cyclic Carbonate

Morikawa

Sudo

Nishida

et al. 2005

Macro Chemistry & Physics

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Summary: To clarify the cationic copolymerization behavior of epoxide and cyclic carbonate, the copolymerization behavior of glycidyl phenyl ether (GPE) with seven‐membered cyclic carbonate (7CC) was carried out using methyl trifluoromethanesulfonate (MeOTf) as a cationic initiator. The addition of 7CC accelerated the consumption rate of GPE, and the resulting copolymers were richer in 7CC‐derived unit compared to the feed ratio of 7CC. During the copolymerization, a large amount of five‐membered cyclic carbonate having a phenoxymethyl group (PM‐5CC) was produced as a by‐product, which suggests the corresponding spiroorthocarbonate was formed as an intermediate and that residual oxytetramethylene (OTM) unit was incorporated into the copolymer sequence. From 1H NMR analysis, it was found that the copolymers had a statistically random sequence consisting of GPE, 7CC, and OTM units. magnified image

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Cationic ring‐opening polymerization of six‐membered cyclic carbonates with ester groups

Cited by 23 publications

References 26 publications

A review of low density porous materials used in laser plasma experiments

A review of low density porous materials used in laser plasma experiments

Highly Chemoselective Catalytic Coupling of Substituted Oxetanes and Carbon Dioxide

Cationic Copolymerization Behavior of Glycidyl Phenyl Ether with Seven‐Membered Cyclic Carbonate

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