Abstract
Novel surface active maleate and methacrylate monomers based on derivatives of ω-hydroxy carboxylic acids have been synthesized. The monomers are comprised of hydrophobic alkyl chains and hydrophilic poly(ethylene glycol), quaternary ammonium, sulfonate and carboxylic fragments. Synthesized monomers sufficiently reduce surface tension at the aqueous solution-air interface. The copolymerization of synthesized monomers with 5-tert-butylperoxy-5-methyl-2-hexene-3-yne monomer and N-vinylpyrrolidone in solvent and emulsion copolymerization of synthesized peroxide containing surface active monomer with styrene have been carried out. The synthesized surface active monomers have been shown to be suitable emulsifiers for obtaining polystyrene colloid dispersions. It has been ascertained that the surface active copolymers obtained can form stable interpolyelectrolyte complexes with oppositely charged polymers.
Similar content being viewed by others
Abbreviations
- IPEC:
-
Interpolyelectrolyte complex
- Surfmer:
-
Surface active monomer
- VEP:
-
5-tert-Butylperoxy-5-methyl-2-hexene-3-yne
References
Kulsherstha AS, Mahapatro A (2008) Polymers of biomedical application. ACS Symp Ser 977:1–7
Vincenzini P, D’arrigo G (2008) Shape-memory polymers for biomedical application. Adv Sci Technol 54:96–102
Ulery BD, Nair LS, Laurencin CT (2011) Biomedical applications of biodegradable polymers. J Polym Sci B Polym Phys 49:832–864
Ward MA, Georgiou TK (2011) Thermoresponsive polymers for biomedical applications. Polymers 3:1215–1242
Guimard NK, Gomez N, Schmidt CE (2007) Conducting polymers in biomedical engineering. Prog Polym Sci 32:876–921
Zhang Y, Chu D, Zheng M, Kissel T (2012) Biocompatible and degradable poly(2-hydroxyethyl methacrylate) based polymers for biomedical applications. Polym Chem 3:2752–2759
Tian H, Tang Z, Zhuang X, Chen X, Jing X (2012) Biodegradable synthetic polymers: preparation, functionalization and biomedical application. Prog Polym Sci 37:237–280
Puskas JE, Chen Y (2004) Biomedical application of commercial polymers and novel polyisobutylene-based thermoplastic elastomers for soft tissue replacement. Biomacromolecules 4:1141–1154
George PM, Lyckman AW, LaVan DA, Hegde A, Leung Y, Avasare R, Testa C, Alexander PM, Langer R, Sur M (2005) Fabrication and biocompatibility of polypyrrole implants suitable for neural prosthetics. Biomaterials 17:3511–3519
Hassler C, Boretius T, Stieglitz T (2011) Polymers for neural implants. J Polym Sci B Polym Phys 49:18–33
Sabir MI, Xu X, Li L (2009) A review on biodegradable polymeric materials for bone tissue engineering applications. J Mater Sci 44:5713–5724
Liechty WB, Kryscio DR, Slaughter BV, Peppas NA (2010) Polymers for drug delivery systems. Annual Rev Chem Biomol Eng 1:149–173
Larson N, Ghandehari H (2012) Polymeric conjugates for drug delivery. Chem Mater 24:840–853
Pan H, Kopecek J (2008) Multifunctional water-soluble polymers for drug delivery. Fundam Biomed Technol 4:81–142
Abulateefeh SR, Spain GS, Aylott JW, Chan WC, Garnett MC, Alexander C (2011) Thermoresponsive polymer colloids for drug delivery and cancer therapy. Macromol Biosci 11:1722–1734
Kim S, Kim JH, Jeon O, Kwon IC, Park K (2009) Engineered polymers for advanced drug delivery. Eur J Pharm Biopharm 71:420–430
Vilar G, Tulla-Puche J, Albericio F (2012) Polymers and drug delivery systems. Curr Drug Deliv 9:367–394
Shaik RM, Korsapati M, Panati D (2012) Polymers in controlled drug delivery systems. Int J Pharma Sci 2:112–116
Hunter AC, Moghimi SM (2010) Cationic carriers of genetic material and cell death: a mitochondrial tale. Biochimica Biophysica Acta 1797:1203–1209
Srinivas R, Sanjoy S, Chaudhuri A (2009) Cationic amphiphiles: promising carriers of genetic materials in gene therapy. Chem Soc Rev 38:3326–3338
Zhu L, Mahato RI (2010) Lipid and polymeric carrier-mediated nucleic acid delivery. Expert Opin Drug Deliv 7:1209–1226
Hajji P, David L, Gerard JF, Kaddami H, Pascault JP, Vigier G (1999) Synthesis-morphology-mechanical properties relationships of polymer-silica nanocomposite hybrid materials. MRS Proc 576:357
Pyun J (2007) Nanocomposite materials from functional polymers and magnetic colloids. Polym Rev 47:231–263
Sung D, Park S, Jon S (2012) Facile immobilization of biomolecules onto various surfaces using epoxide-containing antibiofouling polymers. Langmuir 28:4507–4514
Ho K, Cole N, Chen R, Willcox MD, Rice SA, Kumar N (2012) Immobilization of antibacterial dihydropyrrol-2-ones on functional polymer supports to prevent bacterial infections in vivo. Antimicrob Agents Chemother 56:1138–1141
Shen L (2011) Biocompatible polymer/quantum dots hybrid materials: current status and future developments. J Funct Biomater 2:355–372
Nagai K (1994) Polymerization of surface active monomers and applications. Macromolecular Symposia 84:29–36
Kohut AM, Hevus OI, Voronov SA (2004) Synthesis and properties of 4-(ω-methoxyoligodimethylsiloxanyl)butylmaleate; a new surfmer. J Appl Polymer Sci 93:310–313
Ottewill RH, Satgurunathan R (1988) Non-ionic lattices in aqueous media. Part 2. Stability to add electrolytes. J Colloid Polym Sci 266:543–547
Gramain P, Frere Y (1986) Preparation of monomethoxy-poly(ethylene oxide) acrylate and methacrylate and its polymerization: self-gelling polymers. Polym Commun 27:16–18
Tsaur SL, Fitch RM (1987) Preparation and properties of polystyrene model: i. Preparation of surface active monomers and model colloids derived therefrom. J Colloid Interface Sci 115:450–462
Volkov V, Rodionova R (2006) Synthesis and properties of synthetic polymer latexes with copolymerized emulsifiers. Fibre Chem 38:359–364
Hevus O, Kohut A, Fleychuk R, Zaichenko A, Pashinnik V, Shermolovich Y (2007) Novel surface active maleate monomers for obtaining non–emulsified latexes. React Eng 2:F5–F6
Yoshimura T, Koide Y, Shosenji H, Esumi K (2002) Preparation and surface active properties of telomere type anionic surfactant from maleic anhydride. J Surfact Deterg 5:257–262
Nilson K, Mellin L, Nederberg F, Bowden T (2007) Addition of thiol-containing ligands to a surface-active Michael acceptor. Macromolecules 40:901–908
Mekkil S, Saidi-Besbes S, Elaisarri A, Valour JP (2010) Synthesis of new anionic and cationic polymerizable surfactants for emulsion polymerization of styrene. Macromolecular Symposia 286:100–106
Hevus O, Kohut A, Fleychuk R, Mitina N, Zaichenko O (2007) Colloid systems based on the basis of novel reactive surfmers. Macromolecular Symposia, Selected Contributions from the 3rd International Symposium on “React 2007” 254:117–121
Jaeger W, Bohrisch J, Laschewsky A (2010) Synthetic polymers with quaternary nitrogen atoms—synthesis and structure of the most used type of cationic polyelectrolytes. Prog Polym Sci 35:511–577
Narain R, Armes S (2003) Synthesis and aqueous solutions properties of novel sugar methacrylate based homopolymers and block copolymers. Biomacromolecules 4:1746–1758
Klee EJ, Lehmann U (2010) Novel 2-(ω-phosphonooxy-2-oxaalkyl)acrylate monomers for self-etching self-priming one part adhesive. Beilstein J Org Chem 6:766–772
Cho HG (2010) Preparation and characterization of novel acrylic monomers. J Applied Polym Sci 116:736–742
Li W, Matjaszewski K (2011) Cationic surface-active monomers as reactive surfactants for AGET emulsion ATRP of n-butyl methacrylate. Macromolecules 44:5578–5585
Senhaji O, Robin JJ, Achchoubi M, Boutevin B (2004) Synthesis and characterization of new methacrylic phosphonated monomer surface active monomer. Macromolecular Chem Phys 205:1039–1050
Soula O, Gyout A, Williams N (1993) Styrenic surfmer in emulsion copolymerization of acrylic monomers. Copolymerization and film properties. J Polym Sci Part A: Polym Chem Ed 37:4202–4217
Narain R, Jhurry D, Wulf G (2002) Synthesis and characterization of polymers containing linear sugar moieties as side groups. Eur Polym J 38:273–280
Ito K, Tanaka H, Tanaka K (1991) Poly(ethylene oxide) macromonomers. Micellar polymerization in water. Macromolecules 24:2348–2354
Mishra MK (1994) Macromolecular design: concept and practice. Polymer Frontiers International Inc., New York, pp 161–227
Terao K, Nakamura Y, Norisuye T (1999) Solution properties of polymacromonomers consisting of polystyrene. 2. Chain dimensions and stiffness in cyclohexane and toluene. Macromolecules 32:711–716
Furukashi H, Kawaguchi S, Itsuno S (1997) Synthesis, polymerization, and dispersion copolymerization of poly(ethylene oxide) macromonomers carrying methacryloyloxyalkyl end groups. Colloid Polym 275:227–233
Maniruzzaman M, Kawaguchi S, Ito K (2000) Micellar copolymerization of styrene with poly(ethylene oxide) macromonomer in water: approach to unimolecular nanoparticles via pseudo-living radical polymerization. Macromolecules 33:1583–1592
Ito K, Hashimura K, Itsuno S (1991) Poly(ethylene oxide) macromonomers. 8. Preparation and polymerization of hydroxypoly(ethylene oxide) macro-monomers. Macromolecules 24:3977–3981
Busci A, Forkada J, Gibanel S (1998) Monodisperse polystyrene latex particles functionalized by the macromonomer technique. Macromolecules 31:581–620
Yoshinaga K, Nakashima F, Nishi T (1999) Polymer modification of colloidal particles by spontaneous polymerization of surface active monomers. Colloid Polym Sci 277:136–144
Cheng CJ, Fu LQ, Bai XX, Liu SJ, Shen L, Fan WQ, Li HX (2013) Facile synthesis of gemini surface active ATRP initiator and its use in soap free AGET ATRP mini-emulsion polymerization. Chem Pap 67:336–341
O’Donell J, Schumacher GE, Antonucci JM, Skrtic D (2009) Structure-composition-property relationships in polymeric amorphous calcium phosphate-based dental composites. Materials 2:1929–1954
Dahlgren AG, Claesson PM, Audebert R (1994) Highly charged cationic polyelectrolytes on mica: influence of polyelectrolyte concentration on surface forces. J Colloid Interface Sci 166:343–349
Tang MX, Szoka FC (1997) The influence of polymer structure on the interactions of cationic polymers with DNA and morphology of the resulting complexes. Gene Ther 8:823–832
Kawadkar J, Chauhan MK (2010) The potential of thiolated polymers for peptide drug delivery. Int J Pharma Biol Arch 1:209–218
Zaichenko A, Mitina N, Shevchuk O, Rayevska K, Lobaz V, Skorohoda T, Stoika R (2008) Development of novel linear, block and branched oligoelectrolytes and functionally targeting nanoparticles. Pure Appl Chem 80:2309–2326
Kohut A, Fleychuk R, Hevus O, Voronov S (2007) Macroinitiators on the basis of new peroxide surface active monomers. Chem Chem Technol 1:83–86
Hevus I, Pikh Z (2007) Novel surface active succinate monomers and initiators for obtaining reactive polymers. Macromolecular Symposia 254:103–108
Buller K, Pearson D (1973) Organic synthesis [Russian translation], vol 2. Mir, Moscow
Kostruba A, Zaichenko A, Mitina N, Rayevska K, Hertsyk K (2008) Kinetics of the formation and structure of oligoperoxide nanolayers and grafted polymer brushes on glass plate surface. Central Eur J Phys 6:454–461
Reichardt C, Welton T (2011) Solvents and solvents effects in organic chemistry. Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Liu YL, Huang CT (2006) Investigation of oxidation of cyclic ketones and synthesis of ω-bromoalkanoic acids. Int J Appl Sci Eng 4:235–241
Abele S, Zicmanis A, Graillat C et al (1999) Cationic and zwitterionic polymerizable surfactants: quaternary ammonium dialkyl maleates. 1. Synthesis and characterization. Langmuir 15:1033–1044
Organicum (1979) Practicum in organic chemistry [Russian translation], Vol. 2. Mir, Moscow
Hubbart P, Brittain JW (1998) Mechanism of amine-catalyzed ester formation from an acid chloride and alcohol. J Org Chem 63:677–683
Borzenkov M, Dolynska L, Kochubei V, Nadashkevic Z, Hevus O (2011) The obtaining of functional surface-active monomers based on tert-butylperoxy-6-hydroxyhexanoate. Chem Chem Technol 5:363–366
Herk A (2005) Chemistry and technology of emulsion polymerization. Blackwell Publishing Ltd, Chennai
Dahneke BE (1983) Measurement of suspended particles by quasielastic light scattering. Wiley, New York
Oxley J, Smith J, Brady J, Dubnikova F, Kosloff R, Zeiri L, Zeiri Y (2008) Raman and infrared fingerprint spectroscopy of peroxide-based explosives. Appl Spectrosc 62:906–915
Lin IJ, Moudgil BM, Somasundaran P (1973) Estimation of the effective number of -CH2- groups in long-chain surface active agents. Colloid Polym Sci 252:407–414
Pompe T, Zschoche S, Herold N et al (2003) Maleic anhydride—a versatile platform for molecular biosurface engineering. Biomacromolecules 4:1072–1079
Cheng K, Ram IM (2013) Advanced delivery and therapeutic applications of RNAI. Wiley, New York
Arshady R (1992) Suspension, emulsion and dispersion polymerization: a methodological survey. Colloid Polym Sci 270:717–732
Cho I, Lee KW (1985) Morphology of latex particles formed by poly(methyl methacrylate)-seeded, emulsion polymerization of styrene. J Appl Polym Sci 30:1903–1926
Monteiro JM, Barbeyrac J (2001) Free-radical polymerization of styrene in emulsion using a reversible addition-fragmentation chain transfer agent with a low transfer constant: effect on rate, particle size, and molecular weight. Macromolecules 34:4416–4423
Author information
Authors and Affiliations
Corresponding author
About this article
Cite this article
Borzenkov, M., Mitina, N., Lobaz, V. et al. Synthesis and Properties of Novel Surface Active Monomers Based on Derivatives of 4-Hydroxybutyric Acid and 6-Hydroxyhexanoic Acid. J Surfact Deterg 18, 133–144 (2015). https://doi.org/10.1007/s11743-014-1640-z
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11743-014-1640-z