We propose three approaches to obtain flame-retardant benzoxazines. In the first approach, we synthesize a novel benzoxazine (dopot-m) from a phosphorus-containing triphenol (dopotriol), formaldehyde, and methyl amine. Dopot-m is copolymerized with a commercial benzoxazine [6',6-bis(3-phenyl-3,4-dihydro-2H-1,3-benzoxazineyl)methane (F-a)] or diglycidyl ether of bisphenol A (DGEBA). The thermal properties and flame retardancy of the F-a/dopot-m copolymers increase with the content of dopot-m. As for the dopot-m/DGEBA curing system, the glass-transition temperature of the dopot-m/DGEBA copolymer is 252 degrees C, which is higher than that of poly (dopot-m). The 5% decomposition temperature of the dopot-m/DGEBA copolymer increases from 323 to 351 degrees C because of the higher crosslinking density caused by the reaction of phenolic OH and epoxy. In the second approach, we incorporate the element phosphorus into benzoxazine via the curing reaction of dopotriol. and F-a. After the curing, the thermal properties of the F-a/dopotriol copolymers are almost the same as those of neat poly(F-a), and this implies that we can incorporate the flame-retardant element phosphorus into the polybenzoxazine without sacrificing any thermal properties. In the third approach, we react dopo with electron-deficient benzoxazine to incorporate the element phosphorus. After the curing, the glass-transition temperatures of polybenzoxazines decrease slightly with the content of dopo, mainly because of the smaller crosslinking density of the resultant polybenzoxazines. (c) 2006 Wiley Periodicals, Inc
A novel phosphorus-containing trifunctional novolac (dopotriol) was synthesized through the addition reaction of 9,10-dihydro-9-oxa-10-phosphaphenanthrene 10-oxide and rosolic acid. The structure of dopotriol was confirmed with NMR spectroscopy and elemental analyses. The dopotriol was blended with phenol novolac in the ratios of 10/0, 8/2, 6/4, 4/6, 2/8, and 0/10 to serve as a curing agent for diglycidyl ether of bisphenol A. Thermal properties, such as the glass-transition temperature, thermal decomposition temperature, and flame retardancy, moisture absorption, and dielectric properties of the cured epoxy resins were evaluated. The activity and activation energy of curing were studied with the methods of Kissinger and Ozawa by dynamic differential scanning calorimetry scans. The glass-transition temperatures of the cured epoxy resins were 138-159 degrees C, increasing with the phosphorus content. This is rarely seen in the literature after the addition of a flame-retardant element. The flame retardancy increased with the phosphorus content, and a UL-94 V-0 grade was achieved with a phosphorus content of 1.87%. Similar dielectric properties and moisture absorption were observed for these phosphorus-containing epoxy resins, and this implied that the addition of phosphorus to epoxy did not affect the dielectric properties and moisture absorption. (c) 2005 Wiley Periodicals, Inc
We synthesized a novel phosphorus‐containing triamine [9,10‐dihydro‐9‐oxa‐10‐phosphaphenanthrene 10‐yl‐tris(4‐aminophenyl) methane (dopo‐ta)] from the nucleophilic addition of 9,10‐dihydro‐9‐oxa‐10‐phosphaphenanthrene 10‐oxide and pararosaniline chloride, using triethylamine as an acid receiver. We confirmed the structure of dopo‐ta by IR, mass, and NMR spectra and elemental analysis. dopo‐ta served as a curing agent for diglycidyl ether of bisphenol A (DGEBA) and dicyclopentadiene epoxy (hp7200). Properties such as the glass‐transition temperature (Tg), thermal decomposition temperature, flame retardancy, moisture absorption, and dielectric properties of the cured epoxy resins were evaluated. The Tg's of cured DGEBA/dopo‐ta and hp7200/dopo‐ta were 171 and 190 °C, respectively. This high Tg phenomenon is rarely seen in the literature after the introduction of a flame‐retardant element. The flame retardancy increased with the phosphorus content, and a UL‐94 V‐0 grade was achieved with a phosphorus content of 1.80 wt % for DGEBA/dopo‐ta/diamino diphenylmethane (DDM) systems and 1.46 wt % for hp7200/dopo‐ta/DDM systems. The dielectric constants for DGEBA/dopo‐ta and hp7200/dopo‐ta were 2.91 and 2.82, respectively, implying that the dopo‐ta curing systems exhibited low dielectric properties. © 2005 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 43: 5971–5986, 2005
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