Pentaerythritol ester plasticizer

Hercolube [Aqualon], TM for synthetic lubricant base stocks. J15 Saturated aliphatic ester of pentaerythritol for plasticizing vinylidene chloride. 

Pentaerythritol esters can be used instead of phthalic acid esters when low volatility is one of the major factors in the choice of plasticizer for PVC. Pentaerythriol triacrylate can be used to plasticize PVC and to produce-cross-links under UV radiation. Such plasticized cross-linked PVC has some application in the cable industry. 

In the mid-1970s, Hercules Chemical Company introduced two polyol ester plasticizers, Hercoflex 600 and Hercoflex 707. These plasticizers were prepared by the esterification of pentaerythritol and dipentaerythritol with a mixture of short-chain acids, predominately C6 acid. Although a few PVC applications and patents were developed, because of high costs, they have met with limited commercial success in PVC, although the products continue to be sold into the elastomer market in both North America and in Europe. A PVC plasticizer based on the pentaerythritol ester prepared with predominately C5 acids plus lesser amounts of C7 and C9 acids was patented in 1995 [41] as a low smoke plasticizer. The pentaerythritol ester prepared from C5 acids [42] is now being promoted by the Perstorp Group as a new phthalate alternative under the product brand Pevalen. 

Since Maly first esterified rosin in 1865, practically every conceivable ester of rosin has been prepared, including the glycerol ester, called ester gum, introduced in 1900 for lacquers and printing inks. The methyl ester of hydrogenated rosin is used as a plasticizer in lacquers. Pentaerythritol esters, unmodified and modified with maleic anhydride and phenol-formaldehyde, are used in varnishes. In 1937, the coatings industry used 20 million pounds of phenolic resins modified with ester gum in 1987,66 million pounds were used. Phenolic resins modified with up to 80% ester gum were called 4-hour enamels. Because these enamels possess excellent resistance to hot water and alkali, ester gum replaced damar, copal, and kauri gums in paints, lacquers, and enamels in combination with tung oil. 

Polyols. Several important polyhydric alcohols or polyols are made from formaldehyde. The principal ones include pentaerythritol, made from acetaldehyde and formaldehyde trimethylolpropane, made from -butyraldehyde and formaldehyde and neopentyl glycol, made from isobutyraldehyde and formaldehyde. These polyols find use in the alkyd resin (qv) and synthetic lubricants markets. Pentaerythritol [115-77-5] is also used to produce rosin/tall oil esters and explosives (pentaerythritol tetranitrate). Trimethylolpropane [77-99-6] is also used in urethane coatings, polyurethane foams, and multiftmctional monomers. Neopentyl glycol [126-30-7] finds use in plastics produced from unsaturated polyester resins and in coatings based on saturated polyesters. 

Cy—oxo-derived acids are the principal derivatives of the C —oxo aldehydes, and ia analogy to oxo aldehyde market appHcations, are used chiedy to make neopolyol esters, ie, those based on neopentyl glycol, trimethylolpropane, or pentaerythritol. These synlubes are employed almost entirely ia aeromotive appHcations. Heptanoic acid is also employed to make tetraethylene glycol diheptanoate, a plasticizer used with poly(vinyl butyral). 

Pentaerythritol tetranitrate (PETN) (3) is a powerful explosive which exhibits considerable brisance on detonation (VOD 8310 m/s at = 1.77 g/cm ). It is the most stable and least reactive of the common nitrate ester explosives. The relatively high sensitivity of PETN to friction and impact means that it is usually desensitized with phlegmatizers like wax and the product is used in detonation cord, boosters and as a base charge in detonators. Pentaerythritol tetranitrate can be mixed with synthetic polymers to form plastic bonded explosives (PBXs) like detasheet and Semtex-IA. A cast mixture of PETN and TNT in equal proportions is known as pentolite and has seen wide use as a military explosive and in booster charges. The physical, chemical and explosive properties of PETN commend its use as a high explosive. 

Although this phenol can be used in gasoline, it is too volatile for use in most plastics, especially in thin sections, as in fibers and films. For these uses, analogues of higher molecular weight, such as the ester of pentaerythritol (13.6), are used. 

The most important costabilizers in PVC formulations used mainly in combination with mixed metal salts are alkyl-aryl-phosphites to improve early color. Epoxy compounds, for example, epoxidized fatty esters such as epoxidized soy bean oil, react directly with HCl or substitute labile chlorine atoms, for example, in the presence of zinc ions. Furthermore, the epoxidized fatty esters act as plasticizers. Polyols such as pentaerythritol or dipentaerythritol and P-diketones act as complexing agents and deactivate the negative effect of the formed zinc chloride. Hydrotalcites... 

A novel flame retarding plasticizer is based on polyetltylene stibnite phosphate esters. It contains all essential elements present in compounds having flame retarding properties, such as Sb, P, and halogens. The plasticizer has the advantage of a uniform distribution of antimony oxide which is formed in situ but it is not sufficiently stable at elevated temperamres and to hydrolysis. " Low smoke generation was obtained with a novel plasticizer based on pentaerythritol. ... 

Other Low-Volatility Monomeric Plasticizers Aside from phthalates, trimellitates, and epoxidized oils, the only other low-volatility monomeric-type plasticizers currently available are shorter-chain fatty acid esters of pentaerythritol (PE) and dipentaerythritol (DPE). The PE ester is in the molecular weight range of the trimellitates and DTDP and thus has comparable volatility to these types of plasticizers. The DPE ester (actually a blend of PE and DPE esters) approaches the higher-molecular-weight range of the epoxidized oils. Both of these products are characterized by low viscosity. 

When mixed esters of polyols are prepared using, in part, a dibasic acid, the product is an ester lubricant that is a low polymer. This leads to a high order of resistance to extraction, bloom, or deposition. Pentaerythritol adipate-stearate is used in clear rigid PVC compounds as an efficient multifunctional lubricant, despite its relatively high cost. The corresponding adipate-oleate, a liquid, is more generally used in plasticized compounds in conjunction with mixed metal stabilizers, particularly if the latter are relatively nonlubricating. 

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