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Residual Olefins in Polypropylene

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Residual Olefins in Polypropylene Applications of Ultraviolet Resonance Raman Spectroscopy: Residual Olefins in Polypropylene P. M. RTT.I.OUGH,* V. L. DeVITO, and S. A. ASHER* She///Deve/opment Company, WesthoUowResearch Center, P. O. Box 1380, Houston, Texas 77251-1380 (P.M.K~); and Department of Chemistry, Universkly of Pitteburgh, Pittsburgh, Pennsylvania 15260 (V.L.D., S.A.S.) Ultraviolet mmo~n~ ]lRmAn spectroleopy is used to probe laser excitation which falls within an electronic retddual olefln in polypropyl~ Ration of the olefln band to absorption of the sample. Since the resonance is with nonr~onantly enhanced polymer mod~ inea'u~ with in- a particular chromophore, the only vibrations which creasing olefln content. No UV photodamage is evident for are enhanced are those associated with this samples which are moved through the laser beam. In chromophore. Thus, resonance excitation of chromo- contrast, an increase in intensity of the o|~/Sn band as a phores is a possible way of overcoming the concen- function of irradiation time is seen in stationary samples of tration problems associated with normal Raman polymer, which probably end{cares photo-oxidative degra- spectroscopy while maintaining vibrational specificity. dation. In the specific example under discussion here, we Index Headings: Ultraviolet resonance 1p~mAn~ Polypropylene; excite in the ultraviolet near 220 nm in resonance OlefmJ. with olefin groups. We demonstrate that UV res- onance Raman spectra of polypropylene excited at 220 nm monitors the olefin content. INTRODUCTION The determination of low levels of olefin content in polymers is a difficult problem whether it is done by EXPERIMENTAL chemical or by spectroscopic methods. Chemical The experimental apparatus has been previously methods, such as Iodine Number, can suffer from described in detail. 2 The tunable UV excitation source interferences such as side reactions or from the need was a frequency-doubled Nd:YAG pumped dye laser to use solvent systems incompatible with the polymer. operated at a 20 Hz repetition rate. The visible dye All previously employed spectroscopic methods also laser output was frequency doubled and mixed with have difficulties. For example, proton NMR does not the Nd:YAG fundamental to generate laser light directly detect the olefin bond and is blind to between 217 and 260 nm. The Raman-scattered light completely substituted olefins. 13C NMR directly was dispersed with a SPEX Triplemate mono- detects the olefinic carbons but can be obscured by chromator and detected with the use of a PARC aromatic resonances if they are present. Vibrational optical multichannel analyzer (OMA). The usual time spectroscopies such as infrared and Raman, on the required to obtain a spectrum was 5 minutes. other hand, are directly sensitive to the olefin group Sampling was done with the use of a 135 degree without being obscured by aromatics. The C=C bond front-surface scattering geometry to minimize stretch, however, is inherently weak in the IR. Thus interference from direct reflection from the exciting IR techniques cannot easily be used to measure laser and to minimize self-absorption of the residual amounts of olefln. The C=C bond is a strong Raman-scattered light by the sample. The samples Raman scatterer, but the normal Raman effect is themselves were standard 250-~m-thick plaques weak, and it is usually difficult to detect concentra- which were held to a sample holder on the shaft of a tions below 10,000 to 5,000 ppm. In addition, quanti- motor with double-sided tape. The samples were tation in Raman spectroscopy is difficult and usually spun at approximately 1800 rpm to minimize the requires a suitable internal standard since laser pow- amount of time any one portion of the annular area er and focusing conditions are difficult to reproduce was in the beam in order to minimize degradation of accurately from sample to sample. 1 the sample (vide infra). Band positions reported are However, one spectroscopic method, resonance accurate to ± 5 cm -1 and were calibrated according to Raman, offers a unique way to enhance the detection the known positions of the Raman lines from limit of specific chromophores. The Raman signal acetonitrile. from a sample can be enhanced by six to eight orders of magnitude by exciting the Raman spectrum using RESULTS AND DISCUSSION The Raman spectrum of a polypropylene sample Received 1 March 1991 obtained with UV excitation (Fig. 1) compares well *Authors to whom correspondence should be sent. with a published Raman spectrum of isotactic Note: This article was prepared on a desk top publishing system polypropylene obtained with visible excitation. 3 Only and furnished as camera ready copy. bands associated with UV absorbing chromophores Volume 45, Number 7, 1991 ooo3-7028/91/4507-106752.oo/0 APPLIED SPECTROSCOPY 1067 © 1991 Society for Applied Spectroscopy ..••. 3.54. mJ/cml 2.12 mJ/cm z ~'i.2o .,hl/¢mi 0.64 rnJ/cm ! 46o a6o .do looo lioo 1~o labo labo 2ooo ill ~ ,,,w, loho ll~ll 1,1bo lilo lixl ~ ~ z,~o WovenumbePa (cm--1) WQvenumber (¢m--1) FIG. 1. RarnJan spectrum of isotactic polypropylene excited at 220 FiG. 2. Laser damage / laser power study of spun polypropylene film. nm. Frequency-labeled bands are not seen in a Raman spectrum of this sample excited by visible light. reaction to form olefins and oxygen-containing spe- cies. We suggest that UV excitation leads to the pro- should be resonantly enhanced. Since the polypropyl- duction of the olefin band seen in Fig. 3. Oxygen-con- ene skeleton consists mainly of singly bonded species taining species would not be seen here due to a lack of (which should absorb only in the vacuum UV), resonance enhancement and to their rapid destruction resonance enhancement of the backbone is not in the beam. expected. The major bands in this spectrum are Figure 4 is the UVRR spectrum of a solution of the consistent with the expected nonresonant excitation of antioxidant AO 330 in acetonitrile. On the basis of the polypropylene by the UV laser. Careful compar- this spectrum, the band at 1590 cm -1 in the poly- ison of the UV-excited and the visible-wavelength- propylene spectra is assigned to an antioxidant such excited Raman spectra shows that the UV-excited as AO 330 or BHT. This antioxidant may have been Raman spectrum contains two bands which do not introduced into the samples during an extraction pro- appear in the visible-wavelength-excited spectrum. cedure of the polypropylene with xylene which con- These bands appear at approximately 1590 and 1640 rained an antioxidant. cm -1. The band at 1640 cm "1 occurs in the expected A suitable internal standard is required for group frequency region for carbon-carbon double bond quantitative comparisons of olefin content. One pos- stretching, while the band at 1590 cm "1 is somewhat sible method of quantitation is to ratio the olefin band lower in frequency than would be normally expected to a band from a suitable polypropylene backbone for assignment to this type of vibration (vide infra). mode whose intensity is effectively constant since it is Because of the high energy carried per photon in not resonantly enhanced (vide supra), and which is the UV, care must be taken to prevent degradation of present at essentially identical concentrations in com- the sample. Figure 2 demonstrates that as long as the parison to the residual olefin. The relative ratio of the sample was spun at a reasonable rate, no changes in 1640 cm "1 olefin band to the 1460 cm -1 methylene the spectrum occurred over approximately a thirtyfold deformation band increases as a function of the olefin change in excitation energy flux density. However, if content for the samples studied here. the sample is not spun, the band at approximately 1640 cm "1 begins to increase rapidly in intensity, CONCLUSIONS eventually overwhelming the rest of the spectrum (Fig. 3). This spectral change does not result from These UV Raman spectral data demonstrate that it laser heating since calculations indicate temperature is possible to detect residual olefins in polymers by increases of only a few degrees. Photo-oxidative resonance enhancement of the ~-~* transition. degradation of polypropylene is a likely mechanism. While quantitative Raman spectroscopy is com- This degredation process has been reviewed by plicated due to the necessity for reproducing beam Carlsson and Wiles.4 These authors suggest that characteristics and focusing with differing samples, it photo-instability in polypropylene derives from hydro- is expected that by ratioing the olefin band to peroxide complexes formed by thermal oxidation of aliphatic hydrocarbon bands UVRR can be used as a the polymer melt and during the processsing of poly- semiquantitative rapid screening technique to probe mer films. Radicals can also be produced from for olefin content. photo-reduction of halides and hydroxides from any catalyst residues present. Hydroperoxides decompose under UV excitation to alkoxy radicals, which can then undergo bond scission in a Norrish Type II 1068 Volume45, Number 7, 1991 J 8 r.J c.) 4oo eoo aoo looo 12oo 14oo ~eoo ~eoo ~o 22oo 2,oo ,6o abo eoo lobo l~bo ~4bo ~eoo ~ebo ~ 22"oo 2-oo Wovenurnber8 (crn- 1) Wavenumber8 (cm-- 1) FIG. 3. Laser damage to stationary sample of polypropylene fi]m. FIG. 4. Raman spectrum of a solution of AO330 in acetonitrile Zero minute exposure refers to spun sample. excited at 220 nm excitation. The solvent spectrum has been subtracted. ACKNOWLEDGMENTS P.M.K. would like to acknowledge John D. Webb of Shell Development Company for first suggesting to him that UVRR could 1. H. BarRn•ka, A. LabudzlnAka, and J. Terpin~ki, Laser Raman be used to study residual olet'ms in polypropylene, and Shell Spectrometry: Analytical Applications (John Wiley & Sons, Development Company for allowing him to publish this work.
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