Ricinoleic acid polymers

Fatty acids have been used previously in the development of polymers for biomedical applications as they are considered to be inert, inexpensive and biocompatible. The main fatty acids which are used as a base for synthesis of biomedical polymers (polyanhydrides) are stearic acid (/), erucic acid (C22 unsaturated fatty acid) dimer (2), bile acid dimer (i), ricinoleic acid 4) and other fatty acids (5), middle long carbon chain (C12 - 15) dibasic acids, such as dodecanedioic, brassylic acid, tetradecandioic acid and pentadecandioic acid (/). 

The incorporation of fatty acids into a polyanhydride chain was investigated using two fatty acids lithocholic acid and ricinoleic acid. Lithocholic acid containing polyanhydrides (Figure 2) were prepared by two step synthesis. Polyanhydrides reached molecular weights of 21000-115000 Da, depending on the polymer composition. Release of model drugs from these polymers showed sustained release of 5FU for almost 3 weeks and triamcinolone for 4 weeks (22). 

Ricinoleic acid is a bifunctional fatty acid containing a hydroxy group along the fatty chain. The presence of both carboxylic and hydroxyl groups allows incorporation of ricinoleic acid into a polymer backbone by formation of an ester bond. The synthesis of poly(ester-anhydride) contains two steps trans-... 

To evaluate the in-vivo gelation mechanism of the polymer, mice were injected with three different volumes of polymer. The polymer remained at the injection site and maintained its shape for 24h post injection as happens when oil is injected in the subcutaneous space. Based on data presented in this work we can classify poly(sebacic-co-ricinoleic acid) as in-situ organogel forming. 

Hayes, D.G. Lipase-catalyzed synthesis of poly-hydric alcohol-poly(ricinoleic acid) ester star polymers. Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 2005, 46 (1), 276-277. 

Other modifications of vegetable oils in polymer chemistry include the introduction of alkenyl functions, the study of novel polyesters and polyethers and the synthesis of semi-interpenetrating networks based on castor oil (the triglyceride of ricinoleic acid) [42], and also the production of sebacic acid and 10-undecenoic acid from castor oil [44]. Additionally, the recent application of metathesis reactions to unsaturated fatty acids has opened a novel avenue of exploitation leading to a variety of interesting monomers and polymers, including aliphatic polyesters and polyamides previously derived from petrochemical sources [42, 45]. 

Castor Oil and Transesterification Derivatives of Castor Oil and Other Oils. Castor oil, consisting mainly of a triglyceride of ricinoleic (12-hydroxyoleic) acid (90% ricinoleic acid, 10% nonhydroxy acids, largely oleic and linoleic acids), is a frequent hydroxyl component of urethane coatings. On the basis of the hydroxyl number, castor oil is 70% trifunctional and 30% difunctional. The presence of castor oil in urethane polymers... 

AI3-00400 Bakers P-6 Baryl Butyl 12-acetoxyoleate Butyl 0-acetylrioinoleate EINECS 205-393-4 Flexricin P 6 NSC 2319 9-Octadeoenolc acid, 12-(acetyloxy)-, butyl ester 9-Octadecenoio acid, 12-(acetyloxy)-, butyl ester, (R-(Z))- 9-Octadecenoic acid, 12-(acetyloxy)-, butyl ester, (R- Z))- (9C1) 9-Octadecenoic acid, 12-(acetyloxy)-, butyl ester, (9Z,12R)- Ricinoleic acid, butyl ester, acetate, A plasticizer used with vinyl polymers, Harcros. 

Figure 22.2 [A] General triglyceride structure and fatty acid percentage composition of common plant oil. [B] Fatty acids commonly used in polymer chemistry [a] oleic acid, [b] linoleic acid, (c) linolenic acid, [d] erucic acid, [e] petroselinic acid, [f] ricinoleic acid, [g] vernolic acid, [h] 10-undecenoic acid (reprinted with permission of Montero de Espinosa et al., 2011, Elsevier [10]].

Chem. Descrip. Ricinoleic acid CAS 141-22-0 EINECS/ELINCS 205-470-2 Uses Chemical intermediate lubricant and rust inhibitor in sol. cutting oils basis for grease, soaps, resin plasticizers, and ethoxylated derivs. modifier for coatings and adhesive polymers used in inks, coatings, plastics, cosmetics and toiletries Regulatory FDA approval... 

Ricinolic acid. See Ricinoleic acid Ricino Viscoii. See PEG-25 castor oil Ricinus communis oil Ricinus oil. See Castor (Ricinus communis) oil Ricon 100. See Styrene/butadiene polymer Ricon 130-, Ricon 131, Ricon 142] Ricon 152] Ricon 153. See 1,2-Polybutadiene Ricon 154. See Vinyl butadiene Ricon 156] Ricon 157] Ricon 159] Ricon 160. 

Formaldehyde/toluenesulfonamide polymer Glyceryl rosinate Neopentyl glycol dibenzoate Ricinoleic acid Sucrose benzoate coating modifier, heat-sealable Hydrogenated rosin... 

The reaction of excess amounts of methyl acrylate and the self-metathesis products of monounsaturated fatty acids like methyl ester of oleic acid with ethylene, produces valuable monomers for polycondensation polymers, as well as precursors for detergents in the presence of a suitable metathesis catalyst. In oleochemistry, azaleic and pelargonic acid were obtained industrially by ozonolysis of oleic acid. Non-linear fatty acid derivatives with two double bonds, (ricinoleic acid maleate) and one double bond (ricinoleic acid succinate) were produced from ricinoleic acid by esterification with maleic and succinic anhydride, respectively. Hydrogenation of this ricinoleic acid succinate yielded 12-hydroxystearic acid succinate which is a monomer for vegetable oil-based polyester. 

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