Azelaic acid polyester

Other polyethers which have found limited application are polyethylene oxides) and some mixed polyester-polyethers such as Peedo-120 (Union Carbide), a diester of poly (1,4-butylene oxide )diol and azelaic acid. 

The segmented polyamide elastomers are synthesized from MDI (4,4 -diisocyanato-diphenylmethane) and dicarboxylic acids and a carboxylic acid terminated aliphatic polyester, polycarbonate or polyether prepolymer with an average molecular weight of M = 500-5000. The dicarboxylic acids used as hard segment extenders are adipic and azelaic acid. Also, poly(ester amide) alloys are obtained using nylon-6,6 or polyesters (PEA/PBT). 

The polyesters made from polyols like glycol, glycerol, pentaerythritol and dicar-boxylic acids like adipic, sebacetic, azelaic acids as starting materials easily reach a molecular weight above 1,000 Daltons. It is well established that molecules with molecular weights above 1,000 normally show a very reduced bioavailability. Data show that esters are in principle hydrolyzed, however those at higher molecular... 

The synthesis of dimeric fatty acids is based on the reaction between a fatty acid with one double bond (oleic acid) and a fatty acid with two double bonds (linoleic acid) or three double bonds (linolenic acid), at higher temperatures in the presence of solid acidic catalysts (for example montmorillonite acidic treated clays). Dimerised fatty acids (C36) and trimerised fatty acids (C54) are formed. The dimer acid is separated from the trimeric acid by high vacuum distillation. By using fatty dimeric acids and dimeric alcohols in the synthesis of polyesters and of polyester polyurethanes, products are obtained with an exceptional resistance to hydrolysis, noncrystalline polymers with a very flexible structure and an excellent resistance to heat and oxygen (Chapter 12.5). Utilisation of hydrophobic dicarboxylic acids, such as sebacic acid and azelaic acid in polyesterification reactions leads to hydrolysis resistant polyurethanes. 

A very important acid is azelaic acid obtained industrially by the ozonolysis of vegetable oils (HOOCfCHJ COOH). Azelaic acid is important as a raw material for polyester-based PU adhesives. 

Azelaic acid (AA), 1,9-nonanedioic acid or heptane-1,7-dicarboxylic acid, is used in manifold application areas. AA is offered in the pharmaceutical field for the treatment of acne and rosacea due to its antibacterial effect [1,2]. However, AA is much more widely applied as a monomer for the production of polymers such as alkyd resins, polyamides, and impact-proof polyesters or for the synthesis of plasticizers, lubricants, lithium complex greases, corrosion inhibitors, dielectric fluids, heat-transfer fluids, metal to glass fluxes, emulsion breakers, waxes, tobacco sheet plasticizers, hot-melt coatings and adhesives, water-soluble coating resins, hydraulic fluids, fungicides, insecticides, and so on [3-7]. 

MDI Polyester dicarboxyhc acids, azelaic acid Segmented poly(amide) elastomers... 

Blending of starch with aliphatic polyesters improves their processability and biodegradability Particularly suitable polyesters are poly(s caprolactone) and its copolymers, or polymers of higher melting point formed by the reaction of 1,4-butandiol with succinic acid or with sebacic acid, azelaic acid, or polydactic acid), poly(hydroxyalkanoates), and aliphatic-aromatic polyesters. 

Interesting products previously developed with the Mater-Bi technology include starch and ethylene-vinyl alcohol (EVOH) copolymers starch and PVA starch and aliphatic polyesters, in particular PCL. It is also possible to use aliphatic polyesters such as those formed by the reaction of glycols such as 1,4-BDO with succinic acid, sebacic acid, adipic acid, azelaic acid, dodecandioic acid or brassylic acid. 

In recent years, Novamont developed a family of aliphatic-aromatic copolyesters with its aliphatic dicarboxylic acid component predominantly based on long chain dicarboxylic acids of natural origin (sebacic acid, azelaic acid and brassylic acid) [56-58]. Compared with aliphatic-aromatic polyesters where the aliphatic dicarboxylic component is a shorter carbon chain length, such as BTA polyesters, these copolyesters do not show the sudden decrease of biodegradation properties above... 

The main monomers for the most common biodegradable polyester production, which can now be obtained from renewable resources are succinic acid, 1,4-butanediol, 1,2-ethanediol, sebacic acid and azelaic acid. 

About 1 million tons of plasticizers are used annuaUy in Western Europe, mainly in the plasticization of PVC. The vast majority of plasticizers (around 90%) are esters of phthalic add (phthalates) with a wide variety of long chain alcohols containing up to 13 carbon atoms. The remainder are also esters or polyesters and include those based on adipic, trimellitic, phosphoric, sebacic or azelaic acids. When considering the possible health aspects of plasticizers it is logical therefore to concentrate on phthalates. 

The physical properties of the copolymers vary with melt point. The copolymers are more flexible as the composition approaches the eutectic point. Indeed, copolymers around the 50/ SO mole ratio of terephthalic/sebacic acid are elastomeric in nature, and were extensively studied by DuPont as elastic fibers. Eutectics are also observed in ethylene terephthalate/adi-pate and butylene terephthalate/sebacate copolymers. Introduction of an additional monomer, for example, sebacic acid or azelaic acid in butylene terephthalate/iosphthalate polymers, results in further modification of the properties. In general, introduction of the aliphatic chains results in lowering of the melting point, increased flexibility, greater adhesion properties, and in the case of crystalline polyesters, a faster ciystallization rate. 

Azelaic acid 9 polyester plasticizer oleic acid 8 28... 

The main part of dicarboxylic acids is used in the manufacture of polyester fibers, and the azelaic acid esters ( -hexyl, cyclohexyl-, wo-octyl-and 2-ethylhexyl ester) are excellent plastisizers and S5mthetic lubricants. 

Azelaic, sebacic, dodecanedioic, and brassyhc acids may be used in copolyetheresteramides (111). Two patents describe additional apphcations for the C-9—C-40 diacids for the preparation of polyester carbonates (112), and the copolymerization of epoxides and carbon dioxide by reaction of either glutaric or adipic acids with zinc oxide (113). 

In the context of this chapter, the use of thermoplastic starch in blends with thermoplastic resins is of the main interest. As shown in Table 16.11, several blends have been developed, e.g., with vinyl alcohol copolymers (EVAl), polyolefins, aliphatic polyesters such as poly-e-caprolactone (PCL) and its copolymers, or polymers of glycols (e.g., 1,4-butanediol) with succinic, sebacic, adipic, azelaic, decanoic or brassihc acids, PCL + PVC. Compatibilization is possible by amylose/EVAl V-type complexes, starch grafted polyesters, chain extenders like diisocyanates, epoxies, etc. [Bastioli et al., 1992, 1993]. 

In standard classification for vinyl plastics used in biomedical applications, a plasticizer is specified with prefix letter The letter is followed by a number from 1 to 14 which characterizes the type of plasticizer (e g., 1 - none, 2 - adipic acid derivative, 3 -azelaic, 4 - benzoic, 5 - citric, 6 - isophthalic, 7 - myristic, 8 - phosphoric, 9 - phthalic, 10 - sebacic, 11 - terephthalic, 12 - poly ether, 13 - polyethylene glycol, 14 - polyesters, 999 - other). The second letter specifies secondary plasticizer (e.g., A - none, B - alkyl epoxy stearates, C - epoxidized tall oil, D - epoxidized soybean oil, E - epoxidized linseed oil, F - epoxidized sunflower oil, Z - other). This classification is used to guide design engineers. Classification is not applicable to long-term implants. If there is a conflict between provisions of this standard and detailed specification for a particular device, the latter takes precedence. 

Polyester plasticizer n. Any of a broad class of plasticizers characterized by having many ester groups in each molecule. They are synthesized from three components (1) A dibasic acid such as adipic, azelaic, lauric, or sebacic acid. (2) A glycol (dihydric alcohol). (3) A monofunctional chain terminator such as a monobasic acid. Molecular weights are low - from 500 to 5,000. Polyester plasticizers are noted for their permanence and resistance to extraction. 

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