New Poly(Hydroxylauric-co-Lactic Acid) Liquid Polymer for Dissolving Lipophilic Drugs


  • Florentino C. Sumera Institute of Chemistry, University of the Philippines, Diliman, Quezon City 1101
  • Shienna Marie A. Pontillas Natural Sciences Research Institute, University of the Philippines, Diliman, Quezon City 1101
  • Josanelle Angela V. Bilo Natural Sciences Research Institute, University of the Philippines, Diliman, Quezon City 1101
  • John Marty Mateo Natural Sciences Research Institute, University of the Philippines, Diliman, Quezon City 1101 Institute of Plant Breeding, University of the Philippines, Los Baños, Laguna 4031



poly(hydroxylauric acid-co-lactic acid), liquid polyester, lactic acid, hydroxy-lauric acid, polycondensation, injectables


A liquid, biocompatible polyester based polymer, which could facilitate injectable formulations by simple mixing with the active substance (drug) is much needed by the pharmaceutical companies. A favourite candidate is polylactic acid (PLA) which is biocompatible and biodegradable. However PLA is solid with high crystallinity. Thus, in this research, hydroxylauric acid (HOLA) was copolymerized with lactic acid (LA) in different ratios by polycondensation technique at 180 °C, without a metal catalyst and avoiding the formation of interfering lactides, to provide a liquid polyester. The copolymers molecular weights were determined by Gel Permeation Chromatography (GPC) and their physical states indicated as solid or liquid were noted. The structures as polyesters were confirmed by FT-IR and 1H NMR spectroscopy. Poly(HOLA:LA)  products from reactant ratios 0:100 is solid, while ratios of 20:80, 40:60 are mixed (paste) and 60:40, 80:20 and 100:0 are liquids. Thus, the liquid polyesters from the polycondensation of HOLA and LA without catalyst  were picked as potential candidates for dissolving hydrophobic drugs that could be used as injectables in controlled drug delivery experiments.


Asmus LR, Gurny R, Möller M. Solutions as solutions – Synthesis and use of a liquid polyester excipient to dissolve lipophilic drugs and formulate sustained-release parenterals. European Journal of Pharmaceutics and Biopharmaceutics 2011;79(3):584-591. Available from: doi: 10.1016/j.ejpb.2011.07.007.

Bitner B, Morlock M, Coli H, Winter G, Kissel T. Recombinant influence of the erythropoietin (rhEPO) loaded poly(lactide-co-glycolide) microspheres: influence of the encapsulation technique and polymer purity on microsphere characteristics. Eur J Pharma Biopharm 1998;45(3):295-305. Available from: doi: 10.1016/S0939-6411(98)00012-5.

Casalme L, Sumera FC. Preparation of hydroxylauric acids for environmental and biomaterial use. Phil J Sci 2013;142(2):175-184.

Casalme L, Sumera FC. Synthesis and Characterization of Poly(ester-urethanes) based on Hydroxylauric acids and L-Lactic acid. Quezon City, Philippines: Natural Sciences Research Institute, University of the Philippines Diliman; 2012.

Deno NC, Jedziniak EJ, Messer LA, Meyer MD, Stroud SG, Tomezsko ES. The hydroxylation of alkanes and alkyl chains. Tetrahedron 1977;33(19):2503-2508. Available from: doi: 10.1016/0040-4020(77)80072-0.

Domb AJ, Nudelman R. Biodegradable polymers derived from natural fatty acids. J Poly Sci A Poly Chem. J. Polym. Sci. A Polym. Chem 1995;33(4):717-725. Available from: doi: 10.1002/pola.1995.080330413.

Slivniak R, Domb AJ. Lactic Acid and Ricinoleic Acid Based Copolyesters. Macromolecules 2005;38(13):5545-5553. Available from: doi: 10.1021/ma0503918.

Drumright RE, Gruber PR, Henton DE. Polylactic Acid Technology. Adv. Mater 2000;12(23):1841-1846. Available from: doi: 10.1002/1521-4095(200012)12:23<1841::AID-ADMA1841>3.0.CO;2-E.

Hiltunen K, Seppala JV, Harkonen M. Effect of catalyst and polymerization condition on the preparation of low molecular weight lactic acid polymers. Macromol. Macromolecules 1997;30(3):373-379. Available from: doi: 10.1021/ma960919w.

Hyon SH, Jamshidi K, Ikada Y. Effects of residual monomer on the degradation of DL-lactide polymer. Polym Int. Polym. Int 1998;46(3):196-202. Available from: doi: 10.1002/(SICI)1097-0126(199807)46:3<196::AID-PI914>3.0.CO;2-Y.

Ikada Y, Tsuji H. Biodegradable polyesters for medical and ecological applications. Macromol. Rapid Commun 2000 Feb;21(3):117-132. Available from: doi: 10.1002/(SICI)1521-3927(20000201)21:3<117::AID-MARC117>3.0.CO;2-X.

Kricheldorf HR, Hachmann-Thiessen H. Copolymerization of epsiloncaprolactone and glycolide – a comparison of bismuth (III) hexanoate and tin(II) octanoate as initiators. J Polym Sci Polym Chem;43(15):3268-3277. Available from: doi: 10.1002/pola.20795.

Maharana T, Mohanty B, Negi YS. Melt–solid polycondensation of lactic acid and its biodegradability. Progress in Polymer Science 2009;34(1):99-124. Available from: doi: 10.1016/j.progpolymsci.2008.10.001.

Middleton JC, Tipton AJ. Synthetic biodegradable polymers as orthopedic devices. Biomaterials. Biomaterials 2000;21(23):2335-2346. Available from: doi: 10.1016/S0142-9612(00)00101-0.

Rothen-Weinhold A, Oudry N, Schwach-Abdellaoui K, Frutiger-Hughes S, Hughes GJ, Jeannerat D, et al. Formation of peptide impurities in polyester matrices during implant manufacturing. European Journal of Pharmaceutics and Biopharmaceutics 2000;49(3):253-257. Available from: doi: 10.1016/S0939-6411(00)00066-7.

Stjerndal A, Finne-Wistrand A, Albertsson AC, Backesjo CM, Lindgren U. Minimization of residual tin in the controlled Sn(II) octoate-catalyzed polymerization of epsilon caprolactone. J Biomed Mater Res 2008 Dec;87(4):1086-1091. Available from: doi: 10.1002/jbm.a.31733.

Soderagard A, Solt M. Properties of lactic acid based polymers and their correlation with composition. Prog Polym Sci. Progress in Polymer Science 2002;27(6):1123-1163. Available from: doi: 10.1016/S0079-6700(02)00012-6.

Trimaille T, Möller M, Gurny R. Synthesis and ring-opening polymerization of new monoalkyl-substituted lactides. J. Polym. Sci. A Polym. Chem;42(17):4379-4391. Available from: doi: 10.1002/pola.20251.

Trimaille T, Gurny R, Moller M. Synthesis and properties of novel poly(hexyl substituted lactides) for pharmaceutical applications. Chimia. CHIMIA 2005;59(6):348-352. Available from: doi: 10.2533/000942905777676344.

Trimaille T, Gurny R, Möller M. Poly(hexyl-substituted lactides): Novel injectable hydrophobic drug delivery systems. J. Biomed. Mater. Res 2007;80A(1):55-65. Available from: doi: 10.1002/jbm.a.30888.

Wang SG, Cui WG, Zei Bei J . Bulk and surface modifications of polylactide. Anal Bioanal Chem;381(3):547-556. Available from: doi: 10.1007/s00216-004-2771-2.




How to Cite

Sumera, F. C., Pontillas, S. M. A., Bilo, J. A. V., & Mateo, J. M. (2017). New Poly(Hydroxylauric-co-Lactic Acid) Liquid Polymer for Dissolving Lipophilic Drugs. KIMIKA, 28(1), 20–25.



Research Articles