A novel benzoxazine monomer with methacrylate functionality and its thermally curable (co)polymers

Polymer Bulletin

Volumn 66, Issue 2, 2011, Pages 165-174

  Koz, Banu ^a   Kiskan, Baris ^a   Yagci, Yusuf ^a  

^a ISTANBUL TECHNICAL UNIVERSITY   (Turkey)

Author keywords

Benzoxazine; Copolymer; Methacrylate; Polybenzoxazine; Thermal curing; Thermoset

Indexed keywords

BENZOXAZINE; BENZOXAZINE MONOMERS; CHEMICAL COMPOSITIONS; CURING BEHAVIOR; ESTERIFICATION REACTIONS; ETHYL METHACRYLATES; METHACRYLATE; METHACRYLOYL CHLORIDE; NMR SPECTROSCOPY; POLYBENZOXAZINE; THERMAL CURING; THERMAL GRAVIMETRIC ANALYSIS; THERMAL PROPERTIES;

BOUNDARY ELEMENT METHOD; CHLORINE COMPOUNDS; COPOLYMERIZATION; COPOLYMERS; CURING; DIFFERENTIAL SCANNING CALORIMETRY; ESTERIFICATION; ESTERS; FREE RADICALS; FUNCTIONAL POLYMERS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMER BLENDS; POLYMERS; STYRENE; THERMODYNAMIC PROPERTIES; THERMOGRAVIMETRIC ANALYSIS; THERMOSETS;

FREE RADICAL POLYMERIZATION;

EID: 79751535835     PISSN: 01700839     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00289-010-0261-6     Document Type: Article

References (30)

1. JA Cid YX Wang H Ishida 1999 Cationic polymerization of benzoxazine monomers by boron trifluoride complex Polym Polym Compos 7 (Pubitemid 129588354)
2. YX Wang H Ishida 1999 Cationic ring-opening polymerization of benzoxazines Polymer 40 4563 4570 1:CAS:528:DyaK1MXjtFGntLo%3D 10.1016/S0032-3861(99)00074-9 (Pubitemid 29339477)
3. F Kasapoglu I Cianga Y Yagci T Takeichi 2003 Photoinitiated cationic polymerization of monofunctional benzoxazine J Polym Sci A 41 3320 3328 1:CAS:528:DC%2BD3sXosFSgur0%3D 10.1002/pola.10913 (Pubitemid 37326610)
4. NN Ghosh B Kiskan Y Yagci 2007 Polybenzoxazines-new high performance thermosetting resins: Synthesis and properties Prog Polym Sci 32 1344 1391 1:CAS:528:DC%2BD2sXhtFeis7vL 10.1016/j.progpolymsci.2007.07.002 (Pubitemid 47513190)
5. WJ Burke 1949 3,4-Dihydro-1,3,2H-Benzoxazines. Reaction of p-substituted phenols with N,N-dimethylolamines J Am Chem Soc 71 609 612 1:CAS:528: DyaH1MXhslGnsA%3D%3D 10.1021/ja01170a063
6. WJ Burke C Weatherbee 1950 3,4-Dihydro-1,3,2H-benzoxazines. Reaction of polyhydroxybenzenes with N-methylolamines J Am Chem Soc 72 4691 4694 1:CAS:528:DyaG3MXhtlyqsA%3D%3D 10.1021/ja01166a094
7. B Kiskan Y Yagci H Ishida 2008 Synthesis, characterization, and properties of new thermally curable polyetheresters containing benzoxazine moieties in the main chain J Polym Sci A 46 414 420 1:CAS:528: DC%2BD1cXhtFeitr8%3D 10.1002/pola.22392
8. B Kiskan B Koz Y Yagci 2009 Synthesis and characterization of fluid 1,3-benzoxazine monomers and their thermally activated curing J Polym Sci A 47 6955 6961 1:CAS:528:DC%2BD1MXhsVymur7N 10.1002/pola.23735
9. R Andreu JA Reina JC Ronda 2008 Carboxylic acid-containing benzoxazines as efficient catalysts in the thermal polymerization of benzoxazines J Polym Sci A 46 6091 6101 1:CAS:528:DC%2BD1cXhtFCrtbjN 10.1002/pola.22921
10. Z Brunovska H Ishida 1999 Thermal study on the copolymers of phthalonitrile and phenylnitrile-functional benzoxazines J Appl Polym Sci 73 2937 2949 1:CAS:528:DyaK1MXkvFCjs70%3D 10.1002/(SICI)1097-4628(19990929)73: 14<2937::AID-APP18>3.0.CO;2-E (Pubitemid 30517279)
11. Pei DF, Gu Y, Cai XX (1998) Structure and curing behavior of a new dibenzoxazine precursor containing allyl group. Acta Polym Sin: 595-598
12. T Agag T Takeichi 2001 Novel benzoxazine monomers containing p-phenyl propargyl ether: Polymerization of monomers and properties of polybenzoxazines Macromolecules 34 7257 7263 1:CAS:528:DC%2BD3MXmsFyisLk%3D 10.1021/ma0107915 (Pubitemid 33025845)
13. B Kiskan F Dogan YY Durmaz Y Yagci 2008 Synthesis, characterization and thermally-activated curing of azobenzene-containing benzoxazines Des Monomer Polym 11 473 482 1:CAS:528:DC%2BD1cXhtlSrtrrK 10.1163/156855508X328167
14. Y Yagci B Kiskan NN Ghosh 2009 Recent advancement on polybenzoxazine: a newly developed high performance thermoset J Polym Sci A 47 5565 5576 1:CAS:528:DC%2BD1MXht1Wit7%2FM 10.1002/pola.23597
15. B Kiskan D Colak AE Muftuoglu I Cianga Y Yagci 2005 Synthesis and characterization of thermally curable benzoxazine-functionalized polystyrene macromonomers Macromol Rapid Commun 26 819 824 1:CAS:528:DC%2BD2MXkvFCktrw%3D 10.1002/marc.200500079 (Pubitemid 40812014)
16. B Kiskan Y Yagci 2005 Synthesis and characterization of naphthoxazine functional poly(epsilon-caprolactone) Polymer 46 11690 11697 1:CAS:528:DC%2BD2MXht1eltrjM 10.1016/j.polymer.2005.09.061 (Pubitemid 41653364)
17. MA Tasdelen B Kiskan Y Yagci 2006 Photoinitiated free radical polymerization using benzoxazines as hydrogen donors Macromol Rapid Commun 27 1539 1544 1:CAS:528:DC%2BD28XhtFWqtLjK 10.1002/marc.200600424 (Pubitemid 44535771)
18. A Yildirim B Kiskan AL Demirel Y Yagci 2006 Synthesis, characterization and properties of naphthoxazine-functional poly(propyleneoxide)s Eur Polym J 42 3006 3014 1:CAS:528:DC%2BD28XhtFSnu7%2FI 10.1016/j.eurpolymj.2006.07.019 (Pubitemid 44572293)
19. B Kiskan Y Yagci 2007 Thermally curable benzoxazine monomer with a photodimerizable coumarin group J Polym Sci A 45 1670 1676 1:CAS:528: DC%2BD2sXkslGhu7k%3D 10.1002/pola.21934 (Pubitemid 46715397)
20. B Kiskan Y Yagci E Sahmetlioglu L Toppare 2007 Preparation of conductive polybenzoxazines by oxidative polymerization J Polym Sci A 45 999 1006 1:CAS:528:DC%2BD2sXis1aksbk%3D 10.1002/pola.21848 (Pubitemid 46479697)
21. B Kiskan B Aydogan Y Yagci 2009 Synthesis, characterization, and thermally activated curing of oligosiloxanes containing benzoxazine moieties in the main chain J Polym Sci A 47 804 811 1:CAS:528:DC%2BD1MXhvFCku7s%3D 10.1002/pola.23197
22. H Kimura A Matsumoto H Sugito K Hasegawa K Ohtsuka A Fukuda 2001 New thermosetting resin from poly(p-vinylphenol) based benzoxazine and epoxy resin J Appl Polym Sci 79 555 565 1:CAS:528:DC%2BD3cXoslajsL0%3D 10.1002/1097- 4628(20010118)79:3<555::AID-APP190>3.0.CO;2-H (Pubitemid 32085753)
23. B Gacal L Cianga T Agag T Takeichi Y Yagci 2007 Synthesis and characterization of maleimide (Co)polymers with pendant benzoxazine groups by photoinduced radical polymerization and their thermal curing J Polym Sci A 45 2774 2786 1:CAS:528:DC%2BD2sXhtVOqtL7I 10.1002/pola.22034 (Pubitemid 47146860)
24. M Ergin B Kiskan B Gacal Y Yagci 2007 Thermally curable polystyrene via click chemistry Macromolecules 40 4724 4727 1:CAS:528:DC%2BD2sXlsFOrsbg%3D 10.1021/ma070549j (Pubitemid 47110769)
25. B Kiskan G Demiray Y Yagci 2008 Thermally curable polyvinyl chloride via click chemistry J Polym Sci A 46 3512 3518 1:CAS:528:DC%2BD1cXmvFWns78%3D 10.1002/pola.22685
26. M Kukut B Kiskan Y Yagci 2009 Self-curable benzoxazine functional polybutadienes synthesized by click chemistry Des Monomers Polym 12 167 176 1:CAS:528:DC%2BD1MXlsFSqtLY%3D 10.1163/156855509X412108
27. B Kiskan Y Yagci 2008 Synthesis and characterization of thermally curable polyacetylenes by polymerization of propargyl benzoxazine using rhodium catalyst Polymer 49 2455 2460 1:CAS:528:DC%2BD1cXlslGrurs%3D 10.1016/j.polymer.2008.03.031
28. K Hemvichian HD Kim H Ishida 2005 Identification of volatile products and determination of thermal degradation mechanisms of polybenzoxazine model oligomers by GC-MS Polym Degrad Stab 87 213 224 1:CAS:528:DC%2BD2cXhtFeitrjF 10.1016/j.polymdegradstab.2003.11.005 (Pubitemid 40154913)
29. T Uyar Z Koyuncu H Ishida J Hacaloglu 2008 Polymerisation and degradation of an aromatic amine-based naphthoxazine Polym Degrad Stab 93 2096 2103 1:CAS:528:DC%2BD1cXhsVSqsLbM 10.1016/j.polymdegradstab.2008.09.003
30. S Mehta S Biederman S Shivkumar 1995 Thermal-degradation of foamed polystyrene J Mater Sci 30 2944 2949 1:CAS:528:DyaK2MXmtlOitro%3D 10.1007/BF00349667