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POLYFUNCTIONAL MACROMONOMERS OBTAINED FROM OF 2, 2-BIS (HYDROXYMETHYL) PROPANOIC ACID AND TALL OIL..

Tuesday, February 18, 2014  
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EA Murillo, C Mejia

ABSTRACT
During the last years, the researching have been focused toward the synthesis of friendly
environmentally materials obtained from renewable resources to reduce the dependence of
petrochemistry industries and to obtain friendly environmentally materials [1-4].
Different macromonomers of 2,2-Bis(hydroxymethyl)propanoic acid (DMPA) modified with tall
oil fatty acids (TOFA), which is obtained from renewable resources, were prepared with oil length
(LO) 50 (LO50), 60 (LO60), 70 (LO70) and 80 (LO80) by a esterification reaction. The structural,
thermal, rheological and films properties of the macromonomers (LO50, LO60, LO70 and LO80)
obtained were studied by acid value, hydroxyl value, infrared analysis (IR), nuclear magnetic
resonance (RMN), mass spectrometry (MS) ultraviolet absorption (UV), dynamic light scattering
(DLS), differential scanning calorimetric (DSC), thermogravimetric analysis (TGA), rheological
analysis, drying time, gloss, flexibility, adhesion and chemical resistance against to solvent.
The acid value obtained of the macromonomers was around to 80 mg KOH/g of sample (this value was obtained so, to guarantee the presence of –COOH groups into macromonomers). The
macromonomers exhibited a reduction in the hydroxyl value with the content of TOFA employed
in the synthesis. Though IR and RMN analyses were evidenced the formations of the
macromonomers and the presence of double bond carbon-carbon, acid groups and OH groups, in their structure. The mass spectrometry analysis showed different molecular ions of repetitive units of DMPA and DMPA units grafted with fatty acids. UV analysis allowed determinate that the
absorption due to double bond carbon-carbon (-C=C-) increased with the content of TOFA
(LO80LO70LO60LO50). The macromonomer hydrodynamic dimensions were mainly
nanometrics. The glass transition temperature decreased with the content of TOFA. The thermal
stability of the macromonomers was higher than 200 °C. The rheological behavior presented by
the macromonomers was Newtonian and the viscosity values () were lower than 2.7 Pa.s. The
properties of drying time, gloss, flexibility, adhesion and chemical resistance were goods.
Since the macromonomers exhibited low viscosity, double bonds, OH groups and COOH groups,
good thermal stability and good film properties, they can be employed as plasticizer, reactive
diluents to alkyd resins, crosslinking agent and functionalizing agent. Furthermore this
macromonomers can be used to obtain environmentally alkyd resins (waterborne or with high solid content).

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References
1Haseebuddin, S.; Parmar, R.; Waghoo, G.; Ghosh, S. Prog. Org. Coat. 2009, 64, 446.
2Manczyk, K.; Szewczyk, P. Prog. Org. Coat. 2002, 44, 99.
3Murillo, E.A.; Lopez, B. L.; Brostow, W. Prog. Org. Coat. 2012, 72, 292.
4Akbarinezhad, E.; Ebrahimi, M.; Kassiriha, S. M.; Khorasani, M. Prog. Org. Coat. 2009 65, 217.