Thermally Curable Acetylene-Containing Main-Chain Benzoxazine Polymers via Sonogashira Coupling Reaction

被引:126
作者
Demir, Kubra Dogan [1 ]
Kiskan, Baris [1 ]
Yagci, Yusuf [1 ]
机构
[1] Istanbul Tech Univ, Fac Sci & Letters, Dept Chem, TR-34469 Istanbul, Turkey
关键词
RING-OPENING POLYMERIZATION; HIGH-PERFORMANCE THERMOSETS; ARYL PROPARGYL ETHERS; PHENOLIC MATERIALS; CLICK CHEMISTRY; CURING KINETICS; POLYBENZOXAZINES; MONOMERS; PRECURSORS; MOIETIES;
D O I
10.1021/ma1029746
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
Propargyl containing thermally curable benzoxazine precursors in the main chain have been synthesized from iodo functional bisbenzoxazine and diacetylenes by Sonogashira coupling reaction. For this purpose, 4,4'-isopropylidenediphenol (Bisphenol A) was reacted with formaldehyde and iodoaniline to form diiodobisbenzoxazine (DIBB). Sonogashira coupling reaction between DIBB and diacetylene bisether (DABE) or diacetylene bisbenzoxazine (DABB) catalyzed by palladium tetrakistriphenylphosphine yields the corresponding main-chain polybenzoxazine precursors with the molecular weights around 2300-3500 Da. The structures of the monomers and the resulting polymers are confirmed by FT-IR and H-1 NMR spectral analysis. Curing behaviors of both the monomer and polymers were studied by differential scanning calorimetry (DSC). Thermal properties of the cured polymers were also investigated by thermogravimetric analysis (TGA).
引用
收藏
页码:1801 / 1807
页数:7
相关论文
共 47 条
[1]   Effect of hydroxyphenylmaleimide on the curing behaviour and thermomechanical properties of rubber-modified polybenzoxazine [J].
Agag, T ;
Takeichi, T .
HIGH PERFORMANCE POLYMERS, 2001, 13 (02) :S327-S342
[2]   Novel benzoxazine monomers containing p-phenyl propargyl ether:: Polymerization of monomers and properties of polybenzoxazines [J].
Agag, T ;
Takeichi, T .
MACROMOLECULES, 2001, 34 (21) :7257-7263
[3]   High-molecular-weight AB-type benzoxazines as new precursors for high-performance thermosets [J].
Agag, Tarek ;
Takeichi, Tsutomu .
JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2007, 45 (10) :1878-1888
[4]   Low-Viscosity Polyether-Based Main-Chain Benzoxazine Polymers: Precursors for Flexible Thermosetting Polymers [J].
Agag, Tarek ;
Geiger, Samuel ;
Alhassan, Saeed M. ;
Qutubuddin, Syed ;
Ishida, Hatsuo .
MACROMOLECULES, 2010, 43 (17) :7122-7127
[5]   STERIC AND ELECTRONIC FACTORS WHICH EFFECT THERMAL CYCLIZATION OF META-SUBSTITUTED ARYL PROPARGYL ETHERS - SYNTHESIS OF 5-SUBSTITUTED AND 7-SUBSTITUTED 3-CHROMENES [J].
ANDERSON, WK ;
LAVOIE, EJ ;
WHITKOP, PG .
JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (07) :881-884
[6]   THERMAL CYCLIZATION OF SUBSTITUTED ARYL PROPARGYL ETHERS - SCOPE AND REGIOSELECTIVITY OF REACTION IN SYNTHESIS OF SUBSTITUTED 3-CHROMENES [J].
ANDERSON, WK ;
LAVOIE, EJ .
JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (22) :3832-3835
[7]   Carboxylic acid-containing benzoxazines as efficient catalysts in the thermal polymerization of benzoxazines [J].
Andreu, R. ;
Reina, J. A. ;
Ronda, J. C. .
JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2008, 46 (18) :6091-6101
[8]   Studies on the thermal polymerization of substituted benzoxazine monomers: Electronic effects [J].
Andreu, R. ;
Reina, I. A. ;
Ronda, J. C. .
JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2008, 46 (10) :3353-3366
[9]   Polysiloxane-Containing Benzoxazine Moieties in the Main Chain [J].
Aydogan, Binnur ;
Sureka, Dilek ;
Kiskan, Baris ;
Yagci, Yusuf .
JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2010, 48 (22) :5156-5162
[10]   3,4-DIHYDRO-1,3,2H-BENZOXAZINES - REACTION OF POLYHYDROXYBENZENES WITH N-METHYLOLAMINES [J].
BURKE, WJ ;
WEATHERBEE, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1950, 72 (10) :4691-4694