Research upon Sultones.

Furukawa, Kiyohisa; Okada, Takeshi; Tamai, Iwao; Oda, Ryohei

doi:10.1246/nikkashi1898.59.221

Cited by 11 publications

(7 citation statements)

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“…Furthermore, we sought quantitative relationships in reaction of sulfonated LDPE films with thiourea. The five‐ and six‐membered ring sultones are known to react with a variety of nucleophiles12 and are believed to react with thiourea as shown in Scheme with fission of the carbonoxygen bond,20 resulting in the formation of a sulfonic acid group and CHSCNHNH 2 . In this reaction, the molar quantity of S element increases at 1 mol by treatment with 1 mol thiourea, while the one of N element increases at 2 moles.…”

Section: Resultsmentioning

confidence: 99%

Study of sulfonation mechanism of low‐density polyethylene films with fuming sulfuric acid

Kaneko¹,

Kumagai²,

Nakamura³

et al. 2003

J of Applied Polymer Sci

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Sulfonation of low-density polyethylene (LDPE) films with fuming sulfuric acid was studied by X-ray photoelectron spectroscopy (XPS) and attenuated total reflectance (ATR) infrared spectroscopy. The ATR spectra showed the formation of CAC double bonds and multiple sulfur atom containing groups for the sulfonation of LDPE films. This led us to propose that the abstraction reaction of hydride ion by sulfur trioxide (SO 3 ) in fuming sulfuric acid might account for the formation of the CAC double bonds. It was considered that after the abstraction reaction, these double bonds react with SO 3 , resulting in the production of alkene sulfonic acids and sultones, along with the formation of sulfate groups as a result of reaction of the double bonds with sulfuric acid. Experimental data by treatment of the sulfonated LDPE films with KOH and thiourea supported the proposed idea, estimating the approximate molar ratio of the products.

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Section: Resultsmentioning

confidence: 99%

Study of sulfonation mechanism of low‐density polyethylene films with fuming sulfuric acid

Kaneko¹,

Kumagai²,

Nakamura³

et al. 2003

J of Applied Polymer Sci

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show abstract

“…In addition to KOH treatment, another chemical modification was carried out by treating the sulfonated PP films (30 min) with thiourea in refluxing ethanol 16. In our previous study on the sulfonation of LDPE films with fuming sulfuric acid, we confirmed the formation of sultones by thiourea treatment, and proposed a new sulfonation mechanism, as shown in Scheme 12.…”

Section: Resultsmentioning

confidence: 85%

Sulfonation of Poly(propylene) Films with Fuming Sulfuric Acid

Kaneko

Sato

2005

Macro Chemistry & Physics

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Summary: Sulfonation is one of the most commonly used methods for the surface modification of polymers. In this study, the sulfonation of poly(propylene) (PP) films with fuming sulfuric acid has been investigated with the focus on the surface reaction. Analysis of the sulfonated PP films by X‐ray photoelectron spectroscopy (XPS), attenuated total reflectance (ATR) infrared spectroscopy, and chemical modification demonstrated the formation of CC double bonds and sulfate groups in the sulfonation process. These results and a comparison with low‐density polyethylene (LDPE) films led us to propose a new sulfonation mechanism involving hydride abstraction and the formation of β‐sultones.

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“…Since C C bonds are unlikely to be produced by treatment with thiourea, it seems appropriate to assume that a reaction between the sultones and thiourea occurred as shown in Scheme 1 (illustrating the case of g-sultone), resulting in the formation of C-S-C bonding. [22] Another effect of the thiourea treatment is the decrease of the number of multiple peaks in the region 1 250-1 080 cm À1 . This is probably because g-and d-sultones, which show multiple absorbance bands in the region 1 250-1 080 cm À1 , reacted with thiourea to produce alkene sulfonic acid, causing the decrease in their number.…”

Section: Thiourea Treatmentmentioning

confidence: 99%

Photosulfonation of Low‐Density Polyethylene Films

Kaneko¹,

Sato

2004

Macro Chemistry & Physics

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Summary: Photosulfonation of low‐density polyethylene (LDPE) films by UV irradiation in the presence of gaseous sulfur dioxide (SO2) and oxygen (O2) was studied by attenuated total reflectance (ATR) infrared spectroscopy and X‐ray photoelectron spectroscopy (XPS). The ATR and XPS analysis and chemical modification of UV‐irradiated LDPE films demonstrated the generation of CC double bonds and sultones in the reaction. These results indicated the possibility that sulfur trioxide (SO3) was produced during the photosulfonation. New pathways for the SO3 reaction with LDPE films, resulting in the formation of sulfonic acid groups, were proposed.Overview of the mechanism proposed for the photosulfonation of low‐density polyethylene by SO3 (produced upon UV‐irradiation of gaseous SO2 and O2).imageOverview of the mechanism proposed for the photosulfonation of low‐density polyethylene by SO3 (produced upon UV‐irradiation of gaseous SO2 and O2).

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Research upon Sultones.

Cited by 11 publications

References 0 publications

Study of sulfonation mechanism of low‐density polyethylene films with fuming sulfuric acid

Study of sulfonation mechanism of low‐density polyethylene films with fuming sulfuric acid

Sulfonation of Poly(propylene) Films with Fuming Sulfuric Acid

Photosulfonation of Low‐Density Polyethylene Films

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