Isosorbide applications

Isosorbide polyurethanes, especially those based on aliphatic isocyanates, may be useful in the same applications as conventional polyurethanes i.e. thermoplastics, coatings, and foams. In fact, excellent rigid foams have been obtained from P(I-MDI)(5). Isosorbide has a low melting point of 61°C and it is suitable for use in reactive injection molding processes alone or in the form of a mixture with other conventional diols. In addition, its polymers may also find specific applications due to the anticipated high complexation ability of the two tetrahydrofuran rings in their isosorbide units. 

There is a growing interest in polymers which contain tetrahydrofuran rings in their main chains because of their good/excellent ability to complex with different cations. The applications, however, are limited by difficult multi-step preparations. Isomannide polymers appear to be attractive candidates and easy alternatives in such applications. Isomannide polyurethanes have been prepared by the same procedure described for isosorbide polyurethanes in the experimental section. Their properties are under investigation. 

DLSA are rigid diols. They have the same skeleton as isosorbide and LAGA. For instance, 1,4 3,6-dilactone of mannosaccharic acid is a dicarbonyl derivative of iso-mannide and monocarbonyl derivative of the lactone of the anhydromannonic acid. Therefore, DLSA could find applications as diols and their polymers are expected to have similar properties to that of isosorbide and LAGA polymers. 

Keywords a,co-Alkanediamines, l,4 3,6-Dianhydrohexitols, Aldaric acids, Aldo-nolactones, Aminoalditols, o-Glucitol, Diaminoalditols, D-Mannitol, D-Xyhtol application, Erythritols, Isoidide, Isomannide, Isosorbide, L-Arabinitol, Lipase-catalysis, Polyamides, Polycarbonates, Polyesteramides, Polyesters, Polyethers, Polyureas, Polyurethanes, Super-acid, Tartaric acids... 

The application of phase-transfer conditions for the successful synthesis of di-0-methylisosorbide was demonstrated.179 The same group investigated the alkylation of isosorbide with a series of alkyl bromides, involving a solid-liquid phase transfer in weakly hydrated organic mixtures.180... 

The continuous worldwide application of isosorbide dinitrate and, since the early eighties, of isosorbide 5-mononitrate also, has given rise to a very great number of publications on different aspects of these drugs. It would be beyond the scope of this report to include all of the work on these two important compounds. The present synopsis is therefore restricted to other novel isohexide derivatives and to some new pharmaceutical applications of known compounds. 

In an application dealing with antithrombotic and antihypertensive compositions, the disulfite 163 of isosorbide was mentioned as one of the possible active ingredients 225 Cardiovascular activities were also claimed for a large... 

Isosorbide, an l,4 3,6-dianhydrohexitol, is readily obtained from the double dehydration of sorbitol. Amongst other chemical derivatives, diesters and diethers of sorbitol have already found application as solvents or plasticizers. Functionalization of the two alcohols groups attached to the rather rigid V-shaped framework of the two... 

Nitrates were used to produce a favourable effect on portal hypertension isosorbide dinitrate, isosorbide mononitrate (55,69,134,136,145,217,218) and glyceryl trinitrate (92, 149). Glyceryl trinitrate can easily be controlled owing to its short half-life of 5 minutes. It is also effective upon transdermal application (10 mg/day). 

Fig. 2 Mean plasma isosorbide dinitrate concentrations after application of isosorbide dinitrate (5 mg) to the buccal and sublingual mucosa in six healthy male volunteer subjects. (Redrawn from Ref.. )...

Fatty esters of sorbitan are commercially available as "Span" surfactants and have many applications. A common industrial route for the production of the Span esters is based on a two-step procedure, with acid-catalyzed sorbitol cyclization to sorbitan, followed by high-temperature alkali-catalyzed transeslerification. Alternatively, the cyclization and esterification can be conducted exclusively with acid catalysts, resulting in the isosorbide dicstcr, which can be applied as plasticizer. Conventional catalysts include p-TsOH and a sulfonic acid resin. 

Synthetic Applications of Phase-tranter Processes 301 Tab. 6.17. Reaction of monobenzyloxy isosorbide with X-R-X under the action of MW irradiation. 

It has been shown that application of previously synthesized ethers of isosorbide was beneficial and enabled the preparation of polyethers in better yields than the polyethers obtained in direct reactions of isosorbide and dibromo or dimesyl alkanes [47, 48]. Moreover, the molecular weights of the polyethers were higher than of those prepared in the earlier work [47] and the molecular weight distributions of new polyethers were similar or lower. Such a microwave-assisted procedure can contribute to the synthesis of alternating polyethers and further modification of their properties. 

Another application of immobilized CAL-B has been discovered by Roche scientists for the synthesis of isosorbide monoacetate (82, Scheme 24) [3]. In... 

Prolonged-release (or slow-release) preparations are useful for water-soluble drugs with short biological half-lives. Hydrophobic CyDs, such as ethylated CyDs, with low aqueous solubilities have been demonstrated to work as slow-release carriers of water-soluble drugs such as isosorbide dinitrate, diltiazem hydrochloride, and 5-fluorouracil [19, 38, 39]. For example, 15 has the most prominent retarding effect for water-soluble molsidomine and diltiazem hydrochloride, after oral administration in dogs. The release of isosorbide dinitrate from 16 film was retarded and the plasma drug level after topical application of the film to rat abdominal skin was maintained at 100 ng mL for about 10 h [41]. 

In the field of plasticizers for PVC, some isosorbide esters give functional performance equivalent to some of the most widely criticized phthalates, such as DEHP. ° As phthalates are used in a wide number of applications (PVC plasticizer, cosmetics, inks, lubricants, etc.) there is significant potential for isosorbide derivatives as an alternative to phthalates. 

Dimethyl isosorbide (DMI) is a colourless liquid with excellent solvent properties. DMI has extremely low toxicity and facilitates the penetration of active ingredients through the epidermis. It has shown interesting properties in the delivery of substances like lactic acid, hydrocortisone, vitamin C and hyalmonic acid. It is a solvent with clear potential for cosmetic and pharmaceutical applications. 

The rate constants for production of the RNS described in Table 1 vary from the order of 10 (mol/L) s to the diffusion limiting rate, which suggests an indirect and sometimes undesirable action of NO, in biological medium. Some known NO-donor agents such as glyceryl trinitrate, pen-taerythrityl tetranitrate, isosorbide mononitrate, and sodium nitroprusside (SNP) have current application in clinical therapy. Diazeniumdiolates,... 

In this chapter we will discuss four types of biomass derived monomers and their application in polyesters three building blocks with a more or less unique structure from the 2004 DoF report (i.e. succinic acid, FDCA, and isosorbide), and one true drop-in replacement (i.e. bio-terephthalic acid). For each type of building block the chemical structure, raw material source, and synthesis will be described. The synthesis and properties of the polyesters will then be discussed and, depending on the type of material, current and future commercial applications will be described. 

The first patents in which isosorbide based polyesters are described are from the 1960s. Most of these were aimed at fibre applications and involved co-polyesters with terephthalic acid and other monomers [18-21]. 

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