Synthesis and properties of phosphorus-containing bio-based epoxy resin from itaconic acid

Science China Chemistry

Volumn 57, Issue 3, 2014, Pages 379-388

  Ma, Songqi ^a   Liu, Xiaoqing ^a   Jiang, Yanhua ^a   Fan, Libo ^a   Feng, Jianxiang ^a   Zhu, Jin ^a  

^a NINGBO INSTITUTE OF MATERIALS TECHNOLOGY AND ENGINEERING   (China)

Author keywords

bio based; DOPO; epoxy resin; flame retardancy; itaconic acid

Indexed keywords

CURING; EPOXY RESINS; GLASS; MECHANICAL PROPERTIES; PHOSPHORUS; THERMOGRAVIMETRIC ANALYSIS;

BIO-BASED; DEGRADATION TEMPERATURES; DOPO; FLAME RETARDANCY; HEXAHYDROPHTHALIC ANHYDRIDES; ITACONIC ACID; REACTIVE FLAME RETARDANTS; THERMAL AND MECHANICAL PROPERTIES;

RESINS;

EID: 84895925300     PISSN: 16747291     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11426-013-5025-3     Document Type: Article

References (58)

1. Bucknall CB, Gilbert AH. Toughening tetrafunctional epoxy-resins using polyetherimide. Polymer, 1989, 30(2): 213-217
2. Lee MC, Ho TH, Wang CS. Synthesis of tetrafunctional epoxy resins and their modification with polydimethylsiloxane for electronic application. J Appl Polym Sci, 1996, 62: 217-225
3. Lin ST, Huang SK. Thermal degradation study of siloxane-DGEBA epoxy copolymers. Eur Polym J, 1997, 33(3): 365-373
4. Raquez JM, Del Glise M, Lacrampe MF, Krawczak P. Thermosetting (bio)materials derived from renewable resources: A critical review. Prog Polym Sci, 2010, 35(4): 487-509
5. Flint S, Markle T, Thompson S, Wallace E. Bisphenol A exposure, effects, and policy: A wildlife perspective. J Environ Manage, 2012, 104: 19-34
6. Chrysanthos M, Galy J, Pascault JP. Preparation and properties of bio-based epoxy networks derived from isosorbide diglycidyl ether. Polymer, 2011, 52(16): 3611-3620
7. Miyagawa H, Mohanty AK, Misra M, Drzal LT. Thermo-physical and impact properties of epoxy containing epoxidized linseed oil, 1-anhydride-cured epoxy. Macromol Mater Eng, 2004, 289(7): 629-635
8. Miyagawa H, MisrA M, Drzal LT, Mohanty AK. Fracture toughness and impact strength of anhydride-cured biobased epoxy. Polym Eng Sci, 2005, 45(4): 487-495
9. Gupta AP, Ahmad S, Dev A. Modification of novel bio-based resin-epoxidized soybean oil by conventional epoxy resin. Polym Eng Sci, 2011, 51(6): 1087-1091
10. Fombuena V, Sanchez-Nacher L, Samper MD, Juarez D, Balart R. Study of the properties of thermoset materials derived from epoxidized soybean oil and protein fillers. J Am Oil Chem Soc, 2013, 90(3): 449-457
11. Stemmelen M, Pessel F, Lapinte V, Caillol S, Habas JP, Robin JJ. A fully biobased epoxy resin from vegetable oils: From the synthesis of the precursors by thiol-ene reaction to the study of the final material. Polym Sci Pol Chem, 2011, 49(11): 2434-2444
12. Hofmann K, Glasser W. Engineering plastics from lignin, 23. Network formation of lignin-based epoxy resins. Macromol Chem Phys, 1994, 195(1): 65-80
13. Hofmann K, Glasser WG. Engineering plastics from lignin. 22. Cure of lignin based epoxy resins. J Adhes, 1993, 40(2-4): 229-241
14. El Mansouri NE, Yuan QL, HUANG FR. Synthesis and characterization of kraft lignin-based epoxy resins. BioResources, 2011, 6(3): 2492-2503
15. El Mansouri NE, Yuan QL, Huang FR. Characterization of alkaline lignins for use in phenol-formaldehyde and epoxy resins. Bio Resources, 2011, 6(3): 2647-2662
16. Koike T. Progress in development of epoxy resin systems based on wood biomass in Japan. Polym Eng Sci, 2012, 52(4): 701-717
17. Liu XQ, Zhang JW. High-performance biobased epoxy derived from rosin. Polym int, 2010, 59(5): 607-609
18. Liu XQ, Huang W, Jiang YH, Zhu J, Zhang CZ. Preparation of a bio-based epoxy with comparable properties to those of petroleum-based counterparts. Express Polym Lett, 2012, 6(4): 293-298
19. Deng LL, Shen MM, Yu J, Wu K, Ha CY. Preparation, characterization, and flame retardancy of novel rosin-based siloxane epoxy resins. Ind Eng Chem Res, 2012, 51(24): 8178-8184
20. Patel M, Patel R, Patel V. Effects of reactive diluent diepoxidized cardanol and epoxy fortifier on curing kinetics of epoxy resin. J Therm Anal Calorim, 1989, 35(1): 47-57
21. Aouf C, Lecomte J, Villeneuve P, Dubreucq E, Fulcrand H. Chemoenzymatic functionalization of gallic and vanillic acids: Synthesis of bio-based epoxy resins prepolymers. Green Chem, 2012, 14(8): 2328-2336
22. Aouf C, Nouailhas H, Fache M, Caillol S, Boutevin B, Fulcrand H. Multi-functionalization of gallic acid. Synthesis of a novel bio-based epoxy resin. Eur Polym J, 2013, 49(6): 1185-1195
23. Cao L, Liu X, Na H, Wu Y, Zheng W, Zhu J. How a bio-based epoxy monomer enhanced the properties of diglycidyl ether of bisphenol A (DGEBA)/graphene composites. J Mater Chem A, 2013, 1(16): 5081-5088
24. Werpy T, Petersen G. Eds. Top Value Added Chemicals from Biomass. Volume I-Results of Screening for Potential Candidates from Sugars and Synthesis Gas. PNNL, NREL, EERE report, 2004
25. Ma SQ, Liu XQ, Jiang YH, Tang ZB, Zhang CZ, Zhu J. Bio-based epoxy resin from itaconic acid and its thermosets cured with anhydride and comonomers. Green Chem, 2013, 15(1): 245-254
26. Zhang C, Huang JY, Liu SM, Zhao JQ. The synthesis and properties of a reactive flame-retardant unsaturated polyester resin from a phosphorus- containing diacid. Polym Adv Technol, 2011, 22(12): 1768-1777
27. Laverty JJ. Hydrosilylation of unsaturated polyesters. J Polym Sci: Polym Lett Edition, 1973, 11(5): 327-332
28. Lin CH, Wu CY, Wang CS. Synthesis and properties of phosphorus-containing advanced epoxy resins. II. J Appl Polym Sci, 2000, 78(1): 228-235
29. Shieh JY, Wang CS. Effect of the organophosphate structure on the physical and flame-retardant properties of an epoxy resin. Polym Sci Pol Chem, 2002, 40(3): 369-378
30. Grand AF, Wilkie CA. Fire Retardancy of Polymeric Materials. Marcel Dekker inc., New York, 2000
31. The European Parliament and the European Council: Off. J. Eur. Union, 2003, Directive 2002/96/EC of 27
32. Ravichandran S, Nagarajan S, Ku BC, Coughlin B, Emrick T, Kumar J, Nagarajan R. Halogen-free ultra-high flame retardant polymers through enzyme catalysis. Green Chem, 2012, 14(3): 819-824
33. Wang ZF, Liu WQ, Hu CH, Ma SQ. Study on the modification of epoxy resin by a phosphorus- and silica-containing hybrid. J Appl Polym Sci, 2011, 121(4): 2213-2219
34. Wang X, Hu Y, Song L, Xing WY, Lu HD. Preparation, flame retardancy, and thermal degradation of epoxy thermosets modified with phosphorous/nitrogen- containing glycidyl derivative. Polym Adv Technol, 2012, 23(2): 190-197
35. Xiong YQ, Zhang XY, Liu J, Li MM, Guo F, Xia XN, Xu WJ. Synthesis of novel phosphorus-containing epoxy hardeners and thermal stability and flame-retardant properties of cured products. J Appl Polym Sci, 2012, 125(2): 1219-1225
36. Zhang WC, Li XM, Fan HB, Yang RJ. Study on mechanism of phosphorus-silicon synergistic flame retardancy on epoxy resins. Polym Degrad Stabil, 2012, 97(11): 2241-2248
37. Zang L, Wagner S, Ciesielski M, Muller P, Doring M. Novel star-shaped and hyperbranched phosphorus-containing flame retardants in epoxy resins. Polym Adv Technol, 2011, 22(7): 1182-1191
38. Wang X, Hu Y, Song L, Yang HY, Xing WY, Lu HD. Synthesis and characterization of a DOPO-substitued organophosphorus oligomer and its application in flame retardant epoxy resins. Prog Org Coat, 2011, 71(1): 72-82
39. Hou M, Liu W, Su Q, Liu Y. Synthesis of a novel phosphorus-containing polysiloxane and its use as the modifier of thermal properties of an epoxy resin. Polimery, 2007, 52(11-12): 836-840
40. Wang CS, Shieh JY. Synthesis and properties of epoxy resins containing 2-(6-oxid-6H-dibenz[c,e] [1,2]oxaphosphorin-6-yl)1,4-benzenediol. Polymer, 1998, 39(23): 5819-5826
41. Wang XD, Zhang Q. Synthesis, characterization, and cure properties of phosphorus-containing epoxy resins for flame retardance. Eur Polym J, 2004, 40(2): 385-395
42. Liu YL, Wu CS, Chiu YS, Ho WH. Preparation, thermal properties, and flame retardance of epoxy-silica hybrid resins. Polym Sci Pol Chem, 2003, 41(15): 2354-2367
43. Perret B, Schartel B, Stöß K, Ciesielski M, Diederichs J, Döring M, Krämer J, Altstädt V. Novel DOPO-based flame retardants in high-performance carbon fibre epoxy composites for aviation. Eur Polym J, 2011, 47(5): 1081-1089
44. g flame retardancy approach for epoxy resins. Polym Degrad Stabil, 2008, 93(2): 557-560
45. Hou MH, Liu WQ, Su QQ, Liu YF. Studies on the thermal properties and flame retardancy of epoxy resins modified with polysiloxane containing organophosphorus and epoxide groups. Polym J, 2007, 39(7): 696-702
46. Wang X, Hu Y, Song L, Xing WY, Lu HD. Thermal degradation mechanism of flame retarded epoxy resins with a DOPO-substitued organophosphorus oligomer by TG-FTIR and DP-MS. J Anal Appl Pyrolysis, 2011, 92(1): 164-170
47. Gu J, Dang J, Wu Y, Xie C, Han Y. Flame-retardant, thermal, mechanical and dielectric properties of structural non-halogenated epoxy resin composites. Polym-Plast Technol Eng, 2012, 51(12): 1198-1203
48. Wang CS, Shieh JY. Phosphorus-containing epoxy resin for an electronic application. J Appl Polym Sci, 1999, 73(3): 353-361
49. Yu D, Liu W, Liu Y. Synthesis, thermal properties, and flame retardance of phosphorus-containing epoxy-silica hybrid resins. Polym Composite, 2010, 31(2): 334-339
50. Yu D, Liu W, Liu Y. Study on heat resistance and flame retardation of polyfunctional epoxy-silica-phosphorus hybrid resins. Chem Lett, 2008, 37(11): 1118-1119
51. Höfer R, Selig M. 10.02-Green chemistry and green polymer chemistry. Polym Sci: A Compr Ref, 2012, 5-14
52. Hofer R. History of the Sustainability concept-renaissance of renewable resources. Sustainable Solutions for Modern Economies, RSC Publishing: Cambridge, 2009, 1-11
53. Liu XQ, Xin WB, Zhang JW. Rosin-based acid anhydrides as alternatives to petrochemical curing agents. Green Chem, 2009, 11(7): 1018-1025
54. Tao ZQ, Yang SY, Chen JS, Fan L. Synthesis and characterization of imide ring and siloxane-containing cycloaliphatic epoxy resins. Eur Polym J, 2007, 43(4): 1470-1479
55. Kissinger HE. Variation of peak temperature with heating rate in differential thermal analysis. J Ind Natl Bur Stand, 1956, 57: 217-221
56. Ozawa T. A modified method for kinetic analysis of thermoanalytical data. J Therm Anal, 1976, 9: 369-373
57. Liu, Y. L, Chou CI. The effect of silicon sources on the mechanism of phosphorus-silicon synergism of flame retardation of epoxy resins. Polym Degrad Stabil, 2005, 90(3): 515-522
58. Liu FH, Wang ZG, Wang YL, Zhang B. Copolymer networks from carboxyl-containing polyaryletherketone and diglycidyl ether of bisphenol-A: Preparation and properties. J Polym Sci Pt B-Polym Phys, 2010, 48(23): 2424-2431