Preparation of oil-modified polycaprolactone and its further modification with benzoxazine for coating purposes

Progress in Organic Coatings

Volumn 76, Issue 1, 2013, Pages 137-146

  Taşdelen Yücedaǧ, Çiǧdem ^a   Erciyes, A Tuncer ^a  

^a ISTANBUL TECHNICAL UNIVERSITY   (Turkey)

Author keywords

Benzoxazine; Coating; Oil modified polycaprolactone; Polycaprolactone; Sunflower oil

Indexed keywords

2 ,4-TOLUENE DIISOCYANATE; BENZOXAZINE; BENZOXAZINE MONOMERS; CAPROLACTONE; CURED BLENDS; CURED FILMS; CURING PROCESS; DRYING PROCESS; FILM PROPERTIES; OIL FRACTIONS; POLYBENZOXAZINE; SOFT FILM; STANNOUS OCTOATE; SUNFLOWER OIL; URETHANE LINKAGE; WEIGHT RATIOS;

BLENDING; COATINGS; CURING; DRYING; ESTERS; FRACTURE MECHANICS; MONOMERS; POLYCAPROLACTONE; RING OPENING POLYMERIZATION; TOLUENE; VEGETABLE OILS;

FILM PREPARATION;

EID: 84869099273     PISSN: 03009440     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.porgcoat.2012.08.022     Document Type: Article

References (46)

1. F. Shahidi Sixth ed. Bailey's Industrial Oil and Fat Products vol. 6 2005 John Wiley & Sons New Jersey
2. J. Dullius, C. Ruecker, V. Oliveira, R. Ligabue, and S. Einloft Chemical recycling of post-consumer PET: alkyd resins synthesis Prog. Org. Coat. 57 2006 123 127
3. F.S. Güner, Y. Yaǧci, and A.T. Erciyes Polymers from triglyceride oils Prog. Polym. Sci. 31 2006 633 670
4. C. Jérôme, and P. Lecomte Recent advances in the synthesis of aliphatic polyesters by ring-opening polymerization Adv. Drug Deliv. Rev. 60 2008 1056 1076
5. G. Rossi, I. Giannakopoulos, L. Monticelli, N.K.J. Rostedt, S.R. Puisto, C. Lowe, A.C. Taylor, I. Vattulainen, and T. Ala-Nissila A MARTINI coarse-grained model of a thermoset polyester coating Macromolecules 44 2011 6198 6208
6. B.A.J. Noordover, R. Duchateau, R.A.T.M. van Benthem, W. Ming, and C.E. Koning Enhancing the functionality of biobased polyester coating resins through modification with citric acid Biomacromolecules 8 2007 3860 3870
7. M.A. Woodruff, and D.W. Hutmacher The return of a forgetten polymer-polycaprolactone in the 21st century Prog. Polym. Sci. 35 2010 1217 1256
8. L. Liu, Y. Wang, X. Shen, and Y. Fang Preparation of chitosan-g- polycaprolactone copolymers through ring-opening polymerization of ε-caprolactone onto phthaloyl-protected chitosan Biopolymers 78 2005 163 170
9. F.A. Sheikh, N.A.M. Barakat, M.A. Kanjwal, S. Aryal, M.S. Khil, and H.-Y. Kim Novel self-assembled amphiphilic poly(ε-caprolactone)-grafted- poly(vinyl alcohol) nanoparticles: hydrophobic and hydrophilic drugs carrier nanoparticles J. Mater. Sci. Mater. Med. 20 2009 821 831
10. M.S. Kim, H. Hyun, Y.H. Cho, K.S. Seo, W.Y. Jang, S.K. Kim, G. Khang, and H.B. Lee Preparation of methoxy poly(ethyleneglycol)-block-poly(caprolactone) via activated monomer mechanism and examination of micellar characterization Polym. Bull. 55 2005 149 156
11. C.Y. Gong, S. Shi, P.W. Dong, B. Yang, X.R. Qi, G. Guo, Y.C. Gu, X. Zhao, Y.Q. Wei, and Z.Y. Qian Biodegradable in situ gel-forming controlled drug delivery system based on thermosensitive PCL-PEG-PCL-hydrogel: Part 1. Synthesis, characterization, and acute toxicity evaluation J. Pharm. Sci. 98 2009 4684 4694
12. R. Jayakumar, and H. Tamura Synthesis, characterization and thermal properties of chitin-g-poly(ε-caprolactone) copolymers by using chitin gel Int. J. Biol. Macromol. 43 2008 32 36
13. L. Najemi, T. Jeanmaire, A. Zerroukhi, and M. Raihane Organic catalyst for ring opening polymerization of ε-caprolactone in bulk. Route to starch-graft-polycaprolactone Starch/Stärke 62 2010 147 154
14. B. Kiskan, and Y. Yagci Synthesis and characterization of naphthoxazine functional poly(ε-caprolactone) Polymer 46 2005 11690 11697
15. S.-A. Gârea, H. Iovu, A. Nicolescu, and C. Deleanu Thermal polymerization of benzoxazine monomers followed by GPC, FTIR and DETA Polym. Test. 26 2007 162 171
16. S. Rimdusit, S. Pirstpindvong, W. Tanthapanichakoon, and S. Damrongsakkul Toughening of polybenzoxazine by alloying with urethane prepolymer and flexible epoxy: a comparative study Polym. Eng. Sci. 45 2005 288 296
17. S.F. Li Synthesis of benzoxazine-based phenolic resin containing furan groups Chin. Chem. Lett. 21 2010 868 871
18. M. Baqar, T. Agag, H. Ishida, and S. Qutubuddin Poly(benzoxazine-co- urethane)s: a new concept for phenolic/urethane copolymers via one-pot method Polymer 52 2011 307 317
19. Y.-C. Su, W.-C. Chen, K.-L. Ou, and F.-C. Chang Study of morphologies and dielectric constants of nanoporous materials derived from benzoxazine- terminated poly(ε-caprolactone)/polybenzoxazine co-polymers Polymer 46 2005 3758 3766
20. H. Ishida, and Y.-H. Lee Synergism observed in polybenzoxazine and poly(ε-caprolactone) blends by dynamic mechanical and thermogravimetric analysis Polymer 42 2001 6971 6979
21. T. Takeichi, and T. Agag High performance polybenzoxazines as novel thermosets High Perform. Polym. 18 2006 777 797
22. 13C NMR spectroscopy Polymer 46 2005 8068 8078
23. H. Ishida, and Y.-H. Lee Study of hydrogen bonding and thermal properties of polybenzoxazine and poly-(ε-caprolactone) blends J. Polym. Sci. B: Polym. Phys. 39 2001 736 749
24. S. Zheng, H. Lü, and Q. Guo Thermosetting blends of polybenzoxazine and poly(ε-caprolactone): phase behavior and intermolecular specific interactions Macromol. Chem. Phys. 205 2004 1547 1558
25. J.M. Stanton Isocyanate-modified drying oils J. Am. Oil Chem. Soc. 36 1959 503 507
26. L.V. Cocks, and C.V. Rede Laboratory Handbook for Oil and Fat Analysis 1966 Academic Press New York
27. M. Xie, J. Shi, L. Ding, J. Li, H. Han, and Y. Zhang Cyclic poly(ε-caprolactone) synthesized by combination of ring-opening polymerization with ring-closing metathesis, ring closing enyne metathesis, or click reaction J. Polym. Sci. A: Polym. Chem. 47 2009 3022 3033
28. B. Koz, B. Kiskan, and Y. Yagci A novel benzoxazine monomer with methacrylate functionality and its thermally curable (co)polymers Polym. Bull. 66 2011 165 174
29. S. Rimdusit, C. Liengvachiranon, S. Tiptipakorn, and C. Jubsilp Thermomechanical characteristics of benzoxazine-urethane copolymers and their carbon fiber-reinforced composites J. Appl. Polym. Sci. 113 2009 3823 3830
30. DIN 53152, Deutsche Normen, DeutsherNormenausschuss (DNA) October, 1959.
31. ASTM D3359-90, Standard test methods for measuring adhesion by tape test. Method B, Annual Book of ASTM Standards, vol. 06.01, 1991, 511 pp.
32. ASTMD 1647-89, Standard test methods for resistance of dried films varnishes to water and alkali, Annual Book of ASTM Standards, vol. 06.01, 1991, 236 pp.
33. C.B. Liu, C.Y. Gong, M.J. Huang, J.W. Wang, Y.F. Pan, Y.D. Zhang, G.Z. Li, M.L. Gou, K. Wang, M.J. Tu, Y.Q. Wei, and Z.Y. Qian Thermoreversible gel-sol behavior of biodegradable PCL-PEG-PCL triblock copolymer in aqueous solutions J. Biomed. Mater. Res. B: Appl. Biomater. 84 2008 165 175
34. A. Harrane, R. Meghabar, and M. Belbachir Kinetics of the ring opening polymerization of ε-caprolactone catalysed by a proton exchanged montmorillonite clay React. Funct. Polym. 66 2006 1696 1702
35. W. Yuan, J. Yuan, M. Zhou, and X. Sui Synthesis, characterization, and thermal properties of dendrimer-star, block-comb copolymers by ring-opening polymerization and atom transfer radical polymerization J. Polym. Sci. A: Polym. Chem. 44 2006 6575 6586
36. J.M. Oh, S.H. Lee, J.S. Son, G. Khang, C.H. Kim, H.J. Chun, B.H. Min, J.H. Kim, and M.S. Kim Ring-opening polymerization of ε-caprolactone by poly(propyleneglycol) in the presence of a monomer activator Polymer 50 2009 6019 6023
37. F. Sanda, H. Sanada, Y. Shibasaki, and T. Endo Star polymer synthesis from ε-caprolactone utilizing polyol/protonic acid initiator Macromolecules 35 2002 680 683
38. D.J. Allen, and H. Ishida Effect of phenol substitution on the network structure and properties of linear aliphatic diamine-based benzoxazines Polymer 50 2009 613 626
39. J. Wang, M.-Q. Wu, W.-B. Liu, S.-W. Yang, J.-W. Bai, Q.-Q. Ding, and Y. Li Synthesis, curing behavior and thermal properties of fluorene containing benzoxazines Eur. Polym. J. 46 2010 1024 1031
40. T. Takeichi, Y. Guo, and S. Rimdusit Performance improvement of polybenzoxazine by alloying with polyimide: effect of preparation method on the properties Polymer 46 2005 4909 4916
41. A.T. Erciyes, F.S. Erkal, and O.S. Kabasakal Investigation of urethane oils based on Ecballium elaterium and P. mahaleb seed oils J. Coat. Technol. 64 1992 61 64
42. O. Persenaire, M. Alexandre, P. Degée, and P. Dubois Mechanisms and kinetics of thermal degradation of poly(ε-caprolactone) Biomacromolecules 2 2001 288 294
43. H.Y. Low, and H. Ishida Mechanistic study on the thermal decomposition of polybenzoxazines: effects of aliphatic amines J. Polym. Sci. B: Polym. Phys. 36 1998 1935 1946
44. H.Y. Low, and H. Ishida Structural effects of phenols on the thermal and thermo-oxidative degradation of polybenzoxazines Polymer 40 1999 4365 4376
45. N.N. Ghosh, B. Kiskan, and Y. Yagci Polybenzoxazines - new high performance thermosetting resins: synthesis and properties Prog. Polym. Sci. 32 2007 1344 1391
46. T. Takeichi, and Y. Guo Preparation and properties of poly(urethane-benzoxazine)s based on monofunctional benzoxazinme monomer Polym. J. 33 2001 437 443