CONF'Department of Chemistry, Colorado State University, Fort Colllins, CO Department of Chemistry, University of California, Imine, CA
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1 'p / /r07,./ ;If") f LJ y L"d POLYMERIZATION OF THE CIS- AND TRANS- ISOMERS OF BIS(TRIETH0XYS1LYL)- 2-BUTENE AND COMPARISON OF THEIR STRUCTURAL PROPERTIES 5 F ) N b - - 9s-Cp9 70c R. M. SHALTOUTt, D.A. LOY*t, J. P. CARPENTERt, K. DORHOUTS,K. J. SHEA tencapsulants and Foams Department, Sandia National Laboratories, Albuquerque, NM , daloy@,sandia.gov CONF'Department of Chemistry, Colorado State University, Fort Colllins, CO Department of Chemistry, University of California, Imine, CA yv(y+o5--received 3UN 2 5 l998 ABSTRACT The cis and trans isomers of bis-(triethoxysilyl)-2-butene were polymerized by the@& gel method under various conditions. The trans isomer formed gels under all conditions. The cis isomer formed gels only under basic conditions. Under acidic conditions it formed soluble resins of molecular weight ranging from to Daltons. Solid state and solution 29Si NMR revealed that the trans isomer formed condensed gels, and that the resins formed by the cis isomer contained cyclic monomers andor ordered oligomers. -TI INTRODUCTION Hydrolysis and condensation of monomers of the general form, (EtO)$i-R-Si(OEt)3 (equation 1; R = arylene-, alkylene-, and alkenylene- bridging groups) results in the formation of highly crosslinked polymeric gels. Properties, such as porosity, of these materials have been shown to be affected by the nature of the organic bridging group, R. Rigid spacers such as arylene-, alkynylene-, or alkenylene- bridging groups afford microporous materials. Monomers with flexible alkylene-spacers longer than five carbons in length polymerize under acidic conditions to give non-porous materials'. Short alkylene spacers such as the ethylene-, propylene-, and butylene- bridging groups permit the monomers to readily undergo cyclization reactions that, under acidic conditions, lengthen gelation from minutes to months2. The preferred ring sizes formed in these cyclizations reactions was six and seven membered rings. Similarly, sol-gel polymerization of ethenylene-bridged monomers revealed that the cis-monomer could undergo intramolecular condensation reactions to form the five membered cyclic disilsesquioxane and a bicyclic dimer composed of two seven membered rings. The trans monomer, on the other hand, polymerized rapidly to give gels with no indication of cyclic disilsesquioxane structures3. R3Si-R1-S& H20 Acid or base catalyst Network Polymer + H20 or ROH (1) Recently, we have focused our research on rigid bridged systems to determine if the substitution geometry has an effect on the products. In particular, an isomer of cis geometry would be expected to be more likely to form cyclic products than a trans isomer (equation 2). For example, if R' is trans or cis ethenylene, the products differ3. The trans isomer formed insoluble gels, and the cis-monomer underwent intramolecular condensation reactions to form A
2 DISCLAIMER This report was prepared as an account of work sponsored by an agency of the United States Government. Neither the United States Government nor any agency thercof, nor any of their employm, makes any warranty, express or implied, or assumes any legal liability or responsibility for the accuracy, completeness, or usefulness of any information, apparatus, product, or process disclosed, or represents that its use would not infringe privately owned rights. Reference herein to any specific commercial product, process, or service by trade name, trademark, manufacturer. or otherwise does not necessarily constitute or imply its endorsement, rcwmmendation, or favoring by the United States Government or any agency thereof. The views and opinions of authors expressed herein do not necessarily state or reflect those of the United States Government or any agency thereof.
3 the five membered cyclic disilsesquioxane and a bicyclic dimer composed of two seven membered rings which can go on to form gels. Here we have extended the study of the effects of substitution geometry to the cis and trans 2-butenylene-bridged monomers. Lengthening the bridging group from the 2-carbon ethenylen-bridged system to the four carbon-bridge while still keeping the carbon-carbon double bond, was intended to have two effects. The cis-butenylene monomer should be able to undergo a cyclization reaction to form a seven-membered cyclic disilsesquioxane. The trans double bond would still be expected to prevent the formation of monomeric cyclic disilsesquioxanes, but the more flexible bridging group, due to the extra methylene units, should make the resultant gels more compliant. This, in turn, should permit the pores to collapse during drying and cause the formation of non-porous gels. HO OH \ I,Si Si, h - / R \ 0 RQ,Si \ I OH Si, / R \ /\,Si Si, + H2OrnOH (2) / R \ EXPERIMENT Synthesis of Starting Materials The cis and trans isomers of bis-(triethoxysilyl)-2-butene were prepared by the copper (I) catalyzed silation of cis and transl,4-dichloro-2-butene with trichlorosilane followed by esterification with triethylorthoformate (Fig. 1). The trans isomer has been previously prepared435. The cis isomer is a new compound and was fully characterized as follows. H NMR (400 MHz, C6D6): 6 = 5.35 (t, 2H, SiCH2CH=CHCH2Si), 3.77 (9, 12H, OCH2CH3), 1.55 (d, 4H, SiCH2CH=CHCH2Si), 1.17 (t, 18H, OCH2CH3). 13C NMR (100.5 MHz, C6D6) 6 = 58.1 (OCH2CH3), 18.7 (OCH2CH3), 18.5 (SiCH2CH=CHCH2Si), 17.1 (, SiCH2CH=CHCH2Si). 29Si NMR (79.5 MHz, C6D6): 6 = The soluble polymers were analyzed using a Polymer Labs PL-GPC210 equipped with 2 mixed bed 5-micron Polymer Labs columns in series, a refractive index detector, and a Precision Detectors PD2040 dual-angle (15 O and 90 ) laser light scattering detector. The instrument was calibrated using a 50,000 g/mol narrow polystyrene standard. The mobile phase was THF at a flow rate of 1.O ml/min. CUCl +- Et3N ) HSiC13 Et20 C b S i u S c 1 3 HC(OEt)3 u (OEt)3Siu Fig. 1. Synthesis of Cis Bis-(triethoxysilyl)-2-butene Si(OEt),
4 Sol Gel Polvmerization The monomers were polymerized under a variety of conditions which involved varying the solvent (THF or ethanol) and the catalyst (HC1, NaOH or NH3). The monomer concentration was maintained at 0.4 M and the water/monomer ratio at 6/1 equivalents. To determine if there were differences between the products from the cis and trans isomers the polymers were tested by several physical techniques. Solid state and solution 29Si NMR revealed differences in extent of polymerization and presence or absence of fine structure (indicating cyclics/oligomers). Nitrogen sorption porosimetry and Scanning Electron Microscopy showed differences in pore sizes and molecular weight measurements on soluble polymers indicated extent of polymerization. Also, differences in gelation time were good indicators of reactivity differences. RESULTS AND DISCUSSION The sol gel polymerization of the two monomers led to gel formation under most conditions studied (Table I). The exceptions were the cis isomer under acidic conditions (entries 1 and 3, Table I) which did not gel even after several months. The products, though ungelled, were relatively high molecular weight polymers with molecular weights of 8.8 X lo4 (entry 1) and 1.8 X lo5 Daltons (entry 3). Table I. Gelation Time Expt. # Cis/Trans Catalyst Solvent Gel Time Cis Trans Cis Trans Cis Trans Cis Trans HC1 HCl HC1 HCl NH3 NH3 NaOH NaOH EtOH EtOH THF THF THF THF EtOH EtOH No gel 14 days No gel 3 days 2 months 28 days 1 hour 1 hour The solid state 29Si NMR spectra of the materials that gelled under basic conditions (entries 6, 7 and 8 in Table I) were very similar - all displaying three broad peaks assigned to TI, T2 and T3 silicons with the T3 peak being largest and the T' the smallest. Under acidic conditions, the gelled polymers (trans only, entries 2 and 4) were almost identical in structure. It was apparent from the data that basic conditions resulted in more condensed polymers than acidic conditions. Solution 29% NMR of ungelled cis-butyenylene-bridged polysilsesquioxanes were quite different. As shown in Fig. 3, the spectra contain many sharp peaks due to monomeric cyclics, cyclic oligomers and their hydrolysis products. The broader resonances farther upfield represent less well defined, higher condensed silsesquioxanes. In an attempt to determine the identity of the compounds giving rise to the sharp peaks, we synthesized the cyclic disilsesquioxane and its dimer shown in Fig. 4 and measured their NMR spectra. Although neither was observed in the solution NMR's of the polymers, the chemical shifts of several prominant, sharp resonances are consistent with their hydrolysis products.
5 The X-ray crystal structure of the tricyclic dimer (Fig. 5) is of interest because it indicates that the dimer has a cis syndiotactic geometry. If the oligomerization process could be continued with the same stereochemical preference, a highly regular cis-syndiotactic ladder polymer would be obtained. Furthermore, the presence of the carbon-carbon double bond in the butenylene bridging group could provide the means for controlling the polymer tacticity through coordination to transition metals. B. Cis/HCl/THF, t, I I Fig 3. Solution 29Si NMR of Soluble Polymers. 29~i NMR: ppm 29Si NMR: ppm Fig. 4. Compounds (or derivatives Thereof) That May Be Present in Soluble Resins.
6 Fig. 5. X-Ray Structure of ClbH42Si404. The gels that formed from the cis and trans monomers were examined by nitrogen sorption porosimetry. All the gels were non-porous except the two that formed within one hour (entries 7 and 8, Table I). Surface area analyses of gels that formed quickly exhibited mesoporous structure by nitrogen sorption porosimetry and a rough aggregate structure by scanning electron microscopy. CONCLUSIONS We have synthesized the cis and trans isomers of 1,4-bis(triethoxysily1)-2-butene monomers and polymerized them under acid and base catalyzed sol-gel conditions. As expected the trans system formed crosslinked, insoluble gels. The cis isomer, by nature of its geometry, formed high molecular weight, soluble polymeric products under acidic conditions. We were able to prepare and isolate both the cyclic disilsesquioxane monomer, and its dimer.
7 . Comparison of their spectral characterization with that of the soluble polymers suggests that the cyclics are present within the polymers. The synthesis of a dimer likely present at some early stage of the polymerization suggests that we may be able to control the reaction and form rigid polymers with controllable tacticity. In addition, most of the gels were found to be non-porous indicating that the gels were, in fact, more compliant than ethenylene-bridged polysilsesquioxanes. REFERENCES 1. H. W. Oviatt, K. J. Shea, J. H. Small, Chem. Mater. 5, 943 (1993). 2. D. A. Loy, J. P. Carpenter, S. A. Myers, R. A. Assink,, J. H. Small, J. Greaves, K. J. Shea, e J. Am. Chem. SOC. 118,8501, (1996). 3. J. P. Carpenter, S. A. Yamanaka, M. D. McClain, D. A. Loy, J. A. Greaves, S. Hobson, K. J. Shea, J. Am. Chem. SOC. Submitted,(1998). 4. R. J. P. Corriu, J. 5. E. Moreau, P. Thiapot, M. W. C. Man, J. Mater. Chem. 4, 987, (1994) 5. Z. Foltynowicz, B. Marciniec, Appl. Organomet. Chem. 11,667 (1997).
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