Thermally curable benzoxazine-modified vegetable oil as a coating material

Journal of Coatings Technology and Research

Volumn 10, Issue 4, 2013, Pages 559-569

  Yildirim, Can ^a   Erciyes, A Tuncer ^a   Yagci, Yusuf ^a,b  

^a ISTANBUL TECHNICAL UNIVERSITY   (Turkey)

^b KING ABDULAZIZ UNIVERSITY   (Saudi Arabia)

Author keywords

Benzoxazine; Coating; Thermoset; Triglyceride; Vegetable oil

Indexed keywords

ACETAL RESINS; COATINGS; CURING; DIFFERENTIAL SCANNING CALORIMETRY; MONOMERS; PLATING; SPECTRUM ANALYSIS; THERMOSETS; VEGETABLE OILS;

BENZOXAZINE; BENZOXAZINE MONOMERS; COATING MATERIAL; PARAFORMALDEHYDES; SYNTHETIC APPROACH; THERMALLY ACTIVATED; TOLUENE DIISOCYANATES; TRIGLYCERIDE;

SUNFLOWER OIL;

EID: 84879169762     PISSN: 15470091     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11998-013-9472-8     Document Type: Article

References (71)

1. Scroeder, HM, Terrill, RL, "Styrenated Drying Oils." J. Am. Oil Chem. Soc., 26 153-157 (1949)
2. Hoogsteen, HM, Young, AE, "Styrenation of Dehydrated Castor Oil." Ind. Eng. Chem., 42 1587-1591 (1950)
3. Saxena, MS, Chand, V, Vasishta, AK, "Styrenation of Tobacco Seed Oil for Surface Coatings." Paintindia, 28 23-26 (1978)
4. Eksik, O, Tasdelen, MA, Erciyes, AT, Yagci, Y, "In Situ Synthesis of Oil-Based Polymer/Silver Nanocomposites by Photoinduced Electron Transfer and Free Radical Polymerization Processes." Composite Interfaces, 17 357-369 (2010)
5. Erkal, FS, Usta, S, Erciyes, AT, Yagci, Y, "Styrenation of Triglyceride Oils by Macromonomer Technique." J. Coat. Technol., 72 107-110 (2000)
6. Gultekin, M, Beker, U, Erkal, FS, Erciyes, AT, Yagci, Y, "Styrenation of Castor Oil Linseed Oil By Macromer Method." Macromol. Mater. Eng., 283 15-20 (2000)
7. Akbas, T, Beker, UG, Guner, FS, Erciyes, AT, Yagci, Y, "Drying and Semidrying Macromonomers. III. Styrenation of Sunflower and Linseed Oils." J. Appl. Polym. Sci., 88 2373-2376 (2003)
8. Erkal, FS, Erciyes, AT, Yagci, Y, "A New Method for the Styrenation of Triglyceride Oils for Surface Coatings." J. Coat. Technol., 65 37-43 (1993)
9. Kabasakal, OS, Guner, FS, Erciyes, AT, Yagci, Y, "Styrenation of Oils Based on Secondary Esters of Castor Oil." J. Coat. Technol., 67 47-51 (1995)
10. Alemdar, N, Erciyes, AT, Yagci, Y, "Styrenation of Triglyceride Oil by Nitroxide Mediated Radical Polymerization." Prog. Org. Coat., 66 99-106 (2009)
11. Alemdar, N, Erciyes, AT, Yagci, Y, "Styrenation of Air-Blown Linseed Oil by Nitroxide-Mediated Radical Polymerization." Prog. Org. Coat., 67 55-59 (2010)
12. Erciyes, AT, Kabasakal, OS, Guner, FS, "Use of Methylolated Abietic Acid and Toluene Diisocyanate in the Modification of Triglyceride Oils." J. Coat. Technol., 63 83-88 (1991)
13. Guner, FS, Gumusel, A, Calica, S, Erciyes, AT, "Study of Film Properties of Some Urethane Oils." J. Coat. Technol., 74 55-59 (2002)
14. Cumurcu, A, Erciyes, AT, "Synthesis and Properties of Alkoxysilane-Functionalized Urethane Oil/Titania Hybrid Films." Prog. Org. Coat., 67 317-323 (2010)
15. Cumurcu, A, Erciyes, AT, "Synthesis and Properties of Alkoxysilane-Functionalized Styrenated Oil Based Polyester." Prog. Org. Coat., 71 147-152 (2011)
16. Demir, K, Kiskan, B, Aydogan, B, Yagci, Y, "Thermally Curable Main-Chain Benzoxazine Prepolymers Via Polycondensation Route." React. Funct. Polym., (2012). doi: 10.1016/j.reactfunctpolym.2012.04.016
17. Kiskan, B, Colak, D, Muftuoglu, AE, Cianga, I, Yagci, Y, "Synthesis and Characterization of Thermally Curable Benzoxazine-Functionalized Polystyrene Macromonomers." Macromol. Rapid Commun., 26 819-824 (2005)
18. Kiskan, B, Yagci, Y, "Synthesis and Characterization of Naphtoxazine Functional Poly(epsilon-caprolactone)." Polymer, 46 11690-11697 (2005)
19. Tasdelen, MA, Kiskan, B, Yagci, Y, "Photoinitiated Free Radical Polymerization Using Benzoxazines as Hydrogen Donors." Macromol. Rapid Commun., 27 1539-1544 (2006)
20. Yildirim, A, Kiskan, B, Demirel, AL, Yagci, Y, "Synthesis, Characterization and Properties of Naphtoxazine-Functional Poly(propyleneoxide) s." Eur. Polym. J., 42 3006-3014 (2006)
21. Ergin, M, Kiskan, B, Gacal, B, Yagci, Y, "Thermally Curable Polystyrene via Click Chemistry." Macromolecules, 40 4724-4727 (2007)
22. Kiskan, B, Demiray, G, Yagci, Y, "Thermally Curable Polysvinyl Chloride Via Click Chemistry." J. Polym. Sci. Part A: Polym. Chem., 46 3512-3518 (2008)
23. Baqar, M, Agag, T, Ishida, H, Qutubuddin, S, "Polymerization Behavior of Methylol-Functional Benzoxazine Monomer." React. Funct. Polym., (2012). doi: 10.1016/j.reactfunctpolym.2012.04.017
24. Altinkok, C, Kiskan, B, Yagci, Y, "Synthesis and Characterization of Sulfone Containing Main Chain Oligobenzoxazine Precursors." J. Polym. Sci. Part A: Polym. Chem., 49 2445-2450 (2011)
25. Kiskan, B, Yagci, Y, "Synthesis and Characterization of Thermally Curable Polyacetylenes by Polymerization of Propargyl Benzoxazine Using Rhodium Catalyst." Polymer, 49 2455-2460 (2008)
26. Kiskan, B, Yagci, Y, Ishida, H, "Synthesis, Characterization and Properties of New Thermally Curable Polyetheresters Containing Benzoxazine Moieties in the Main Chain." J. Polym. Sci. Part A: Polym. Chem., 46 414-420 (2008)
27. Kiskan, B, Aydogan, B, Yagci, Y, "Synthesis, Characterization, and Thermally Activated Curing of Oligosiloxanes Containing Benzoxazine Moieties in the Main Chain." J. Polym. Sci. Part A: Polym. Chem., 47 804-811 (2009)
28. Kukut, M, Kiskan, B, Yagci, Y, "Self-Curable Benzoxazine Functional Polybutadienes Synthesized by Click Chemistry." Des. Mon. Polym., 12 167-176 (2009)
29. Koz, B, Kiskan, B, Yagci, Y, "A Novel Benzoxazine Monomer with Methacrylate Functionality and Its Thermally Curable (Co)polymers." Polym. Bull., 66 165-174 (2011)
30. Tuzun, A, Kiskan, B, Alemdar, N, Erciyes, AT, Yagci, Y, "Benzoxazine Containing Polyester Thermosets with Improved Adhesion and Flexibility." J. Polym. Sci. Part A: Polym. Chem., 48 4279-4284 (2010)
31. Aydogan, B, Sureka, D, Kiskan, B, Yagci, Y, "Polysiloxane-Containing Benzoxazine Moieties in the Main Chain." J. Polym. Sci. Part A: Polym. Chem., 48 5156-5162 (2010)
32. Kiskan, B, Demirel, AL, Kamer, O, Yagci, Y, "Synthesis and Characterization of Nanomagnetite Thermosets Based on Benzoxazines." J. Polym. Sci. Part A: Polym. Chem., 46 6780-6788 (2008)
33. Demir, KD, Tasdelen, MA, Uyar, T, Kawaguchi, AW, Sudo, A, Endo, T, Yagci, Y, "Synthesis of Polybenzoxazine/Clay Nanocomposites by in Situ Thermal Ring-Opening Polymerization Using Intercalated Monomer." J. Polym. Sci. Part A: Polym. Chem., 49 4123-4220 (2011)
34. Calo, E, Maffezzoli, A, Mele, G, Martina, F, Mazzetto, SE, Tarzia, A, Stifani, C, "Synthesis of a Novel Cardanol-Based Benzoxazine Monomer and Environmentally Sustainable Production of Polymers and Bio-composites." Green Chem., 9 754-759 (2007)
35. Zuniga, C, Larrechi, MS, Lligadas, G, Ronda, JC, Galia, M, Cadiz, V, "Polybenzoxazines from renewable diphenolic acid." J. Polym. Sci: Polym. Chem., 49 1219-1227 (2011)
36. Zuniga, C, Lligadas, G, Ronda, JC, Galia, M, Cadiz, V, "Renewable Polybenzoxazines Based in Diphenolic Acid." Polymer, 53 1617-1623 (2012)
37. Zuniga, C, Lligadas, G, Ronda, JC, Galia, M, Cadiz, V, "Self-Foaming Diphenolic Acid Benzoxazine." Polymer, 53 3089-3095 (2012)
38. Ronda, JC, Lligadas, C, Galia, M, Cadiz, V, "A Renewable Approach to Thermosetting Resins." React. Funct. Polym., (2012). doi: 10.1016/j.reactfunctpolym.2012.03.015
39. DIN 53152, Deutsche Normen Herausgegeben vom Deutschen Normenausschuss (DNA), October 1959.
40. ASTM 3359-90, Annual Book of ASTM Standards, pp. 511-514. American Society for Testing and Materials, Philadelphia, PA, 1991
41. ASTM D 2134-93, Annual Book of ASTM Standards, pp. 198-200. American Society for Testing and Materials, Philadelphia, PA, 1991
42. ASTM D 1647-89, Annual Book of ASTM Standards, pp. 236-237. American Society for Testing and Materials, Philadelphia, PA, 1991
43. Cocks, LV, van Rede, C, Laboratory Handbook for Oil and Fat Analysis. American Press, London and New York, 1966
44. Rodrigues, CEC, Silva, FA, Marsaioli, A, Meirelles, AJA, "Deacidification of Brazil Nut and Macadamia Nut Oils by Solvent Extraction: Liquid-Liquid Equilibrium Data at 298.2 K." J. Chem. Eng. Data, 50 517-523 (2005)
45. Monick, JA, Treybal, RE, "Separation of Monoglycerides, Diglycerides and Triglycerides by Liquid-Liquid Extraction." J. Am. Oil. Chem. Soc., 33 193-197 (1956)
46. Kuhrt, NH, Welch, EA, "Method of Obtaining Concentrated Monoglycerides." US Patent 2,727,913, 1955.
47. Chattopadhyay, DK, Raju, KVSN, "Structural Engineering of Polyurethane Coatings for High Performance Applications." Prog. Polym. Sci., 32 352-418 (2007)
48. Ajithkumar, S, Kansara, SS, Patel, NK, "Kinetics of Castor Oil Based Polyol-Toluene Diisocyanate Reactions." Eur. Polym. J., 34 1273-1276 (1998)
49. Stanton, JM, "Isocyanate Modified Drying Oils." J. Am. Oil Chem. Soc., 36 503-507 (1959)
50. Agag, T, Jin, L, Ishida, H, "A New Synthetic Approach for Difficult Benzoxazines: Preparation and Polymerization of 4,4′-diaminodiphenyl Sulfone-Based Benzoxazine Monomer." Polymer, 50 5940-5944 (2009)
51. Lin, CH, Lin, HT, Chang, SL, Hwang, HJ, Hu, YM, Taso, YR, Su, WC, "Benzoxazines with Tolyl, p-hydroxyphenyl or p-carboxyphenyl linkage and the Structure-Property Relationship of Resulting Thermosets." Polymer, 50 2264-2272 (2009)
52. Ning, L, Ning, WD, Kang, YS, "Hydrogen-Bonding Properties of Segmented Polyether Poly(urethane urea) Copolymer." Macromolecules, 30 4405-4409 (1997)
53. Allen, DJ, Ishida, H, "Effect of Phenol Substitution on the Network Structure and Properties of Linear Aliphatic Diamine-Based Benzoxazines." Polymer, 50 613-626 (2009)
54. Takeichi, T, Guo, Y, Agag, T, "Synthesis and Characterization of Poly(urethane-benzoxazine) Films as Novel Type of Polyurethane/Phenolic Resin Composites." J. Polym. Sci. Part A: Polym. Chem., 38 4165-4176 (2000)
55. Baqar, M, Agag, T, Ishida, H, Qutubuddin, S, "Poly(benzoxazine-co- urethane)s: A New Concept for Phenolic/Urethane Copolymers Via One-Pot Method." Polymer, 52 307-317 (2011)
56. Sudo, A, Mori, A, Endo, T, "Promoting Effects of Urethane Derivatives of Phenols on the Ring-Opening Polymerization of 1,3-Benzoxazines." J. Polym. Sci. Part A: Polym. Chem., 49 2183-2190 (2011)
57. Ates, S, Dizman, C, Aydogan, B, Kiskan, B, Torun, L, Yagci, Y, "Synthesis, Characterization and Thermally Activated Curing of Polysulfones with Benzoxazine End Groups." Polymer, 52 1504-1509 (2011)
58. Yang, WP, Macosko, CW, Wellinghoff, ST, "Thermal Degradation of Urethanes Based on 4,4-Diphenylmethane Diisocyanate and 1,4-Butanediol (MDI/BDO)." Polymer, 27 1235-1240 (1986)
59. Choudhury, RBR, "The Preparation and Purification of Monoglcerides. I. Glycerolysis of Oils." J. Am. Oil Chem. Soc., 37 483-486 (1960)
60. Choudhury, RBR, "The Preparation and Purification of Monoglcerides. II. Direct Esterification of Fatty Acids with Glycerol." J. Am. Oil. Chem. Soc., 39 345-347 (1962)
61. Feuge, RO, Gross, AT, "Modification of Vegatable Oils. IX. Purification of Technical Monoglyceride." J. Am. Oil Chem. Soc., 27 117-122 (1950)
62. Schuchardt, U, Sercheli, R, Vargas, RM, "Transesterification of Vegatable Oils: A Review." J. Braz. Chem. Soc., 9 199-210 (1998)
63. Mattil, KF, Sims, RJ, "The Glycerolysis of Fat in Tertiary Aromatic Nitrogenous Bases to Increase Monoglyceride Yield." J. Am. Oil Chem. Soc., 29 59-61 (1952)
64. Cheng, SF, Choo, YM, Ma, AN, Chuah, CH, "Rapid Synthesis of Palm-Based Monoacylglycerols." J. Am. Oil Chem. Soc., 82 791-795 (2005)
65. McKinney, RS, Goldblatt, LA, "Preparation and Some Properties of Tung Oil Monoglycerides." J. Am. Oil Chem. Soc., 34 585-587 (1957)
66. Emtir, MM, Guner, FS, Kabasakal, OS, Erciyes, AT, Ekinci, E, "Kinetics of Esterification Reaction Between Glycerol and Oleic Acid." Lipid/Fett, 97 347-351 (1995)
67. Mohsen-Nia, MN, Khodayari, A, "De-Acidification of Sunflower Oil By Solvent Extraction:(Liquid + Liquid) Equilibrium Data at T(303.15 and 313.15) K." J. Chem. Thermodyn., 40 1325-1329 (2008)
68. Pina, CG, Meirelles, AJA, "Deacidification of Corn Oil By Solvent Extraction In A Perforated Rotating Disc Column." J. Am. Oil Chem. Soc., 77 553-559 (2000)
69. Turkay, S, Civelekoglu, H, "Deacidification of Sulfur Olive Oil. I. Single-Stage Liquid-Liquid Extraction of Miscella with Ethyl Alcohol." J. Am. Oil Chem. Soc., 68 83-86 (1991)
70. Turkay, S, Civelekoglu, H, "Deacidification of Sulfur Olive Oil. II. Multi-Stage Liquid-Liquid Extraction of Miscella with Ethyl Alcohol." J. Am. Oil Chem. Soc., 68 818-821 (1991)
71. Kolstad, JJ, Benson, RD, Bloomer, SD, Tsobanakis, P, "Method of Preparation of Purified Glycerides, and, Producs." US Patent 6,153,773, 2000