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Preparation, Characterization, and Crystallization of Naphthalene-Labeled Polypropylene

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Preparation, Characterization, and Crystallization of Naphthalene-Labeled Polypropylene Polymer Journal, Vol. 32, No. 12, pp 995~993 (2000) Preparation, Characterization, and Crystallization of Naphthalene-Labeled Polypropylene Jun YANG, t Guangxin CHEN, Wanjun LIU, and Jingjiang LIU State Key Laboratory of Poymer Physics and Chemistry, Changchun Institute ofApplied Chemistry, Chinese Academy ofSciences, Changchun 130022, People's Republic of China (Received April 10, 2000; Accepted August 18, 2000) ABSTRACT: Naphthalene-labeled polypropylene (PP) was prepared by melt reaction of maleic anhydride-grafted­ polypropylene (PP-g-MA) with 1-aminonaphthalene in a Barabender mixer chamber. The structure of the product was analyzed with fourier transform infrared (FT-IR), ultraviolet (UV) and fluorescence. The results showed that naphthyl groups grafted onto the PP molecular chains through the imide bonds formed between MA and 1-aminonaphthalene. 4 The content of the chromophores was 1.8 X 10 ·· mo! g - i measured by elemental analysis. Isothermal crystallization be­ havior was studied by differential scanning calorimeter (DSC). Labeled PP had a higher crystallization rate than PP-g­ MA. Wide-angle X-Ray diffraction (WAXD) analysis revealed that labeled PP had higher crystallinity than PP-g-MA. KEY WORDS Melt Reaction I Excimer Fluorescence/ Polypropylene/Naphthalene/ Excimer formation has been widely used to study poly­ DSC analysis of isothermal crystallization revealed that mer physics and processing. This fluorescence quench­ labeled PP has a higher crystallization rate than PP-g­ ing can give information about miscibility of polymer MA as well as a higher crystallinity measured by blends, 1 residual strains in polymer materials,2 chain WAXD. To our knowledge, labeling fluorescent chromo­ folding,3 distribution of functional groups grafted onto a phores to a polymer in melt instead of in solution is polymer backbone,4 chain interactions,5 and conforma­ scarcely reported. The advantage of melt reaction is that tion and dynamics of polymers in dilute solution.6 These this method can produce a wide variety of products than experiments all require polymers to which appropriate the reaction in solution. fluorescent groups are attached. Pyrene and naphtha­ lene are commonly fluorescent probes for this purpose EXPERIMENTAL because ofrelatively higher quantum yield. Many routes have been reported for the preparation of Isotactic polypropylene (model 1300) with melt index polymer probes containing small amounts of fluorescent of 1.20 g/10 min was purchased from Yanshan Petrol­ chromophores. Free-radical copolymerization and poly­ chemicals Co. (Beijing China). Dicumyl peroxide (DCP) mer functional reactions in solution are the main meth­ and maleic anhydride (MAH) were of reagent grade and ods. Cheng7 prepared copolymers of 1-naphthylmethyl used without further purification. 1-Aminonaphthalene methacrylate and methyl methacrylate by free radical was purchased from Xingzhong Chemical Factory in polymerization. Li5 prepared pyrenyl-labeled polysty­ Shanghai, China. rene by copolymerization of styrene and a py-monomer. PP-g-MA was first manufactured by melt mixing of PP The py-monomer is synthesized from 1-pyrenylmethanol melt and MAH in the presence of DCP at 180°C in a Ba­ with m/p-chloromethyl styrene. Mathew et al. 3 synthe­ rabender mixing chamber as described in the litera­ sized the pyrenyl-labeled polystyrene (PS) with the same ture.10 The content of maleic anhydride in PP-g-MA was structure. However, they followed the second route. PS 1.7 wt% as measured by titration. Naphthalene-labeled was chloromethylated first and then 1-pyrenemethanol PP was prepared by melt mixing of PP-g-MA with 1- was added. Similarly, Liaw, et al. 8 incorporated naphthyl aminonaphthalene in excess in a Barabender mixing group into a cationic copolymer and its photophysical re­ chamber. Mixing temperature was controlled at 180°C sponse was used to probe solution behavior on the micro­ and the rotation speed was 50 rpm. Identical processing scopic level. Zhao1 prepared naphthalene-labeled linear was performed for PP-g-MA sample without addition of low density polyethylene (LLDPE) by grafting maleic 1-aminonaphthalene, to obtain a comparative sample anhydride (MA) onto LLDPE first and then the product with the same thermal history. Labeled PP and unla­ reacted with aminonaphthalene in xylene solution. Jao9 beled PP-g-MA were purified by repeated dissolving and reacted maleated ethylene-propylene copolymer with 1- precipitation using a system of xylene and methanol, sol­ pyrenebutylhydrazine in mineral lubricating oil solution vent and precipitation agent, respectively, under a nitro­ to introduce the fluorescent probes. gen atmosphere. This article reports the preparation of naphthalene­ Naphthalene-labeled PP was analyzed on a JFS 66 V labeled polypropylene (PP) by melt reaction of maleated FT-IR spectrophotometer. UV absorption spectra were PP with 1-aminonaphthalene. Characterization indi­ obtained with an UV-2101PC spectrophotometer and cated the succinic anhydride groups on the PP-g-MA film samples of 30 µm in thickness were used. Steady­ chains to react with 1-aminonaphthalene thoroughly. state fluorescence spectra were measured using a SPEX tTo whom correspondence should be addressed (E-mail: [email protected]). 995 J. y ANG et al. pp~ =O Scheme 1. 283nm labeledPP f: j C::cu I' 4500 4000 3500 3000 2500 2000 1500 1000 500 0 .c.. ' 0 Wavenumber (cm·') i <( PP-g-MA Figure 1. FT-IR spectra of PP-g-MA and labeled PP. / 212 spectrometer. Measurement was taken with front­ face geometry from polymer films at an excitation wave­ length of 280 nm. Elemental analysis was performed on 250 300 350 400 450 500 a Vario EL elemental analyzer made in Germany. Wavelength (nm) Crystallization kinetic experiments were carried out 2. lN absorption spectra of PP-g-MA and labeled PP. using a Perkin-Elmer DSC-7 calibrated with indium and Figure zinc standards. Isothermal crystallization kinetics were performed by first heating the sample quickly (at 80°C min -l) to 220°C: in the DSC, holding it at 220°C for 10 1729 cm -l is observed. This new band is attributed to min to eliminate residual and small nuclei that might the absorption of the imide group formed between the 1 act as seed crystals, and then cooling (at ~80°C min- ) pendant succinic anhydride and 1-aminonaphthalene, as the melt to the designated crystallization temperatures, shown in Scheme 1. Similar results were obtained by Tc. Exothermal curves of heat flow as a function of time Jao, et al. 9 In their report, the new band was observed at 1 were recorded and investigated. All operations were per­ 1730 cm - , as a proof of the quantitative conversion of formed under a nitrogen purge. Sample weights were the succinic anhydride to imide. In our work, the clear from 4-6 mg. Relative crystallinity Xt was determined band at 1729 cm - l and disappearance of the two bands by at 1863 cm -l and 1785 cm -l give evidence that the at­ tached succinic anhydride quantitatively reacts with 1- aminonaphthalene. UV absorption spectra of PP-g-MA and labeled PP are (1) shown in Figure 2. The absorption between 270-300 nm is the typical absorption of naphthalene monomers. The peak position is at 283 nm. In the spectrum of PP-g­ MA, characteristic absorption bands of naphthalene are where dH/dt is the rate of heat flow, t0 is the time at not observed in the wavelengths measured in this work. which the sample attained the isothermal condition, as The presence of naphthyl groups in the labeled PP was indicated by a flat base line on the thermal curve after confirmed from these results. the initial spike. Figure 3 gives uncorrected emission spectra of PP-g­ Wide-angle X-Ray diffraction profiles of labeled PP MA and labeled PP at excitation wavelength of 280 nm. and PP-g-MA were obtained using a PW 1700 Philips In the spectrum oflabeled PP, the peak at 337 nm corre­ diffractometer with Cu-Ka, Ni-filtered radiation. The sponds to the isolated naphthalene monomer and broad measurement condition was 40 KV and 30 mA. band at 400 nm corresponds to the excimer complex. Ex­ cimer emission is often structureless relative to the fine RESULTS AND DISCUSSION structure of monomer emission.11 In the spectrum of PP­ g-MA, the peaks mentioned above were not observed. Structure Analysis This indicates again that the labeled PP contains naph­ FT-IR spectra of PP-g-MA and labeled PP are shown thalene chromophores. in Figure 1. Absorbance bands at 1863 cm - l and 1785 The chromophore content oflabeled polymer is usually cm -l for the carbonyl group of the succinic anhydride at­ determined by UV absorption in solution. In this work, tached to the PP backbone were observed in the spec­ unfortunately, no solvent for labeled PP was found at trum of PP-g-MA. These two bands disappeared in the ambient temperature. Hence, an elemental analysis was spectrum of labeled PP and a new absorbance band at used to determine the content of naphthyl groups at- 996 Polym. J., Vol. 32, No. 12, 2000 Naphthalene-Labeled PP Prepared by Melt Reaction 100 - j 337nm lj .. / /"/. 80 J· I / /. >< if i l /. 60 § 0 400nm Ji .. / ;· -•-12s c Ii l " l -•-127 °c 40 I • l0 •. 1 _,._ 129 °c Cll > /1 j l I :;:; -T-131 °C IQ 20 al ii l1· /""''"" 0:: ff 11/. -•-133°C PP-g-MA 0 .. /. 4 6 10 12 14 16 18 20 22 24 26 28 30 Crystallization time t (min) 250 300 350 400 450 500 550 600 Figure 5. Development of relative crystallinity X, with crystalli­ Wavelength (nm) zation time for isothermal melt crystallization oflabeled PP. Figure 3. Typical fluorescence spectra of PP-g-MA and labeled PP. 05 • .. • labeled PP • • .. " • • .. " • 00 • • • .. " • • ::;; • • .. " • X • • .. " • ' -0 5 • • .. " • PP-g-MA " 125°C ..5 • .. • • ..!... -1.0 " 127°C 0) • ..2 .
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