Refractive index of poly(thiocarbonate)s and poly(dithiocarbonate)s

Marianucci, Elisabetta; Berti, Corrado; Pilati, Francesco; Manaresi, P.; Guaita, Marino; Chiantore, Oscar

doi:10.1016/0032-3861(94)90361-1

Cited by 63 publications

(56 citation statements)

References 8 publications

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“…The high refractive indices observed make these polymers, particularly poly(dithiocarbonate)s, potentially interesting for optical applications (i.e., lenses and optical fibers) (303).…”

Section: Polymers Containing Thiocarbonylthio -S-co-s-and Oxycarbonylmentioning

confidence: 99%

Sulfur‐Containing Polymers

Kultys

2010

Encyclopedia of Polymer Science and Technology

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Sulfur-containing polymers, when considering their structure, make up a complex group of macromolecular compounds of varied and often remarkable features that determine their versatile applications.The presence of sulfur atoms in polymer structure, depending on the kind of functional group, can improve some important properties, such as mechanical, electrical, and optical, and then adhesion to metals, resistance to heat, chemicals, radiation, and bacteria, biocompatibility, and so on. These are their more important functional groups: sulfide -S-, polysulfide -S n -, sulfonyl -SO 2 -, sulfinyl -SO-, sulfo -SO 3 H, as well as some organic groups containing sulfur atoms, such as thioester -Sulfur-containing polymers can be used as high performance engineering plastics, chemically stable ion-exchange membranes in electromembrane processes, proton-conducting electrolytes, as well as optical, optoelectronic, and photochemical materials. Some polymers are employed in biomedical applications, for example, sulfopolymers as biomembranes and blood-compatible materials, and polysulfates and polysulfonates as antithrombotic or antiviral agents. The presence of sulfur, particularly in the form of disulfide bridges, plays an important role in biopolymers.The purpose of this review is mainly to present recent advances in the area of sulfur-containing polymers that may not yet have commercial applications. Nevertheless, older but still significant material has been included at the beginning of the discussion of each class. Poly(monosulfide)sPolymers containing a monosulfide linkage in both the main chain and the pendent group are the subject of many detailed studies. A few reviews of the synthesis and properties of all types of polymers have been published (1-4); like the one covering polymer with sulfur in the main chain that appeared in 1992 (3). Polysulfides with controlled and well-defined structures can be easily prepared. Nevertheless, the only commercial poly(monosulfide) is Ryton [Philips Petroleum Co., poly(thio-1,4-phenylene) more frequently referred to as poly(p-phenylene sulfide) or poly(phenylene sulfide) (PPS)].

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“…The high refractive indices observed make these polymers, particularly poly(dithiocarbonate)s, potentially interesting for optical applications (i.e., lenses and optical fibers) (303).…”

Section: Polymers Containing Thiocarbonylthio -S-co-s-and Oxycarbonylmentioning

confidence: 99%

Sulfur‐Containing Polymers

Kultys

2010

Encyclopedia of Polymer Science and Technology

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“…4 (236,237). The high refractive indices observed make these polymers, particularly poly(dithiocarbonate)s, potentially interesting for optical applications (ie, lenses and optical fibers) (238).…”

Section: Sulfur-containing Polymers 365mentioning

confidence: 99%

Sulfur‐Containing Polymers

Kultys¹

2001

Encyclopedia of Polymer Science and Technology

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Vol. 4 SULFUR-CONTAINING POLYMERS 337Nevertheless, the only commercial poly(monosulfide) is Ryton [Philips Petroleum Co., poly(thio-1,4-phenylene) more frequently referred to as poly(p-phenylene sulfide) or poly(phenylene sulfide) (PPS)]. Much effort has been devoted to preparing aromatic compounds in view of their significance as reactive intermediates for the synthesis of high performance linear aromatic polymers by ring-opening polymerization (ROP) (5). In an attempt to develop a novel synthetic method for the preparation of high molecular weight poly(thioarylene)s, macrocyclic aromatic sulfides and disulfides have been intensively prepared (6-14). The coordination chemistry of macrocyclic polysulfides has also received considerable attention during the past years. The thiacrown ether polymer ligands can be used as ion-exchange resins, metal ion adsorbents, and polymeric phase-transfer catalysts (15,16). Molecular systems in which tetrathiafulvalene is incorporated into macrocycles with supplementary donor atoms are potential electroactive cation sensors (17). The π -conjugated polymers have been extensively studied because of their attractive electronic properties. SULFUR-CONTAINING POLYMERSVol. 4The novel partially crystalline polymer (3) with number-average molecular weight (M n ) of up to 5700 was prepared under various conditions by catalyzed self-condensation of 3-hydroxypropyl methoxycarbonylethyl sulfide (4) or 3-hydroxypropyl carboxyethyl sulfide (5) (22). The degree of crystallinity, melting temperature (T m ), T g , and temperature of initial decomposition (T d ) were 36-46%, 37-47 • C, −61 to −70 • C, and 164-260 • C, respectively. The monomers (4) and (5) were prepared by an addition of methyl 3-mercaptopropionate and 3-mercaptopropionic acid with allyl alcohol [107-18-6] catalyzed by AIBN [2,2 -azobis(2-methylpropionitrile), azobisisobutyronitrile, azodiisobutyrodinitrile, 2,2 -azobis(2-methylpropanenitrile), α,α -azodiisobutyronitrile, 2,2 -azobis(isobutyronitrile), 2,2 -dicyano-2,2 -azopropane, Porofor-57, 2,2 -dimethyl-2,2azodipropionitrile, 2,2(-azobis(2-methylpropionitrile))] [78-67-1].An addition of conjugate 1,4-benzenedithiol (A) to 1,4-divinylbenzene (1,4diethenylbenzene, p-divinylbenzene) (B) [105-06-6] was investigated in detail in the presence of the AIBN initiator in toluene at 75 • C (23). It was found that the polymerization proceeded without an induction period, to give a white polymer with a high molecular weight [weight-average molecular weight (M w ) = 110,000] in ∼90% yield for 2 h. In addition, it was confirmed by 1 H nmr, ir, and the sulfur contents that the polymer had an alternating structure of A and B units.The synthesis and radical addition behavior of optically active cysteinebased monomers with mercapto and olefin groups have also been studied (24). N-4-vinylbenzoyl-L-cysteine methyl ester polymerized satisfactorily to afford the corresponding polysulfide (with M n in the range of 7000-23,000) in good yields.A novel one-pot synthesis of sulfur-containing polymers incl...

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“…In recent years, much attention has been paid to sulfur-containing polymers because of their extraordinarily high optical and thermal properties. 1 The most common way to obtain sulfur-containing polymers is the reaction of dithiols with dihalides and phosgene derivatives. 2 Ringopening reactions of cyclic thio compounds can be considered an attractive alternative polymerization route.…”

Section: Introductionmentioning

confidence: 99%

“…11 This work deals with the sub-stituent effect of five-member cyclic dithiocarbonates on cationic ring-opening polymerization and the mechanistic aspects of the polymerization. 1 H and 13 C NMR spectra were recorded on JEOL EX-90 ( 1 H, 90 MHz) and EX-400 ( 1 H, 400 MHz; 13 C, 100 MHz) spectrometers with chloroform-d (CDCl 3 ) as a solvent. The chemical shifts are given in parts per million against tetramethylsilane (TMS) as an internal standard.…”

Section: Introductionmentioning

confidence: 99%

Substituent effect on the cationic ring‐opening polymerization of acyloxymethyl five‐member cyclic dithiocarbonates

Steblyanko

Choi

Sanda

et al. 2001

J. Polym. Sci. A Polym. Chem.

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Five-member cyclic dithiocarbonates were synthesized by the reactions of carbon disulfide with benzoic, p-anisic, p-chlorobenzoic, 1-naphthalenecarboxylic, pnitrobenzoic, and p-(tert-butyl)benzoic glycidyl esters, and their cationic ring-opening polymerizations were carried out with methyl trifluoromethane sulfonate and trifluoromethane sulfonic acid as initiators at room temperature to 80°C. Polymers with number-average molecular weights of 3400 -24,900 were obtained in high yields, and their structures were estimated by NMR and IR spectroscopy. The monomers showed a clear difference in the polymerization rate according to the substituents. The rate of polymerization decreased in the order of p-chlorobenzoic Ն benzoic Ͼ 1-naphthalenecarboxylic Ͼ p-nitro-benzoic Ͼ p-tert-butylbenzoic Ͼ p-anisic. The data of the reaction kinetics, NMR studies, and molecular orbital calculations proved a plausible mechanism involving the participation of p-substituted benzoyloxymethyl groups to stabilize the cationic propagating end. The polymers showed decomposition temperatures with 5% weight loss ranging from 200 to 260°C. No glass-transition temperatures for the polymers were observed below 200°C by differential scanning calorimetry.

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Refractive index of poly(thiocarbonate)s and poly(dithiocarbonate)s

Cited by 63 publications

References 8 publications

Sulfur‐Containing Polymers

Sulfur‐Containing Polymers

Sulfur‐Containing Polymers

Substituent effect on the cationic ring‐opening polymerization of acyloxymethyl five‐member cyclic dithiocarbonates

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