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Article in Press ARTICLE IN PRESS Prog. Polym. Sci. xx (2004) xxx–xxx www.elsevier.com/locate/ppolysci Oligo- and polysilo xanes Yoshimoto Abe*, Takahiro Gunji Department of Pure and Applied Chemistry, Faculty of Science and Technology, Tokyo University of Science, 2641 Yamazaki, Noda, Chiba 278-8510, Japan Received 14 January 2003; revised 5 August 2003; accepted 21 August 2003 Abstract The article reviews the work on the synthesis, properties, and structure of curious oligo- and polysiloxanes which have been done mainly by the authors, referring the related papers. So far as oligosiloxanes, the topic is especially focused on sila- functional siloxanes as the building block for the synthesis of ladder or cube oligosiloxanes, while the another is the polysiloxanes derived from silicic acid and trimethoxysilanes RSi(OMe)3 which are able to form fibers and flexible free- standing films. The review also refers to the new routes for the selective synthesis of sila-functional oligosiloxanes in addition to the reaction control based on the relative reactivity of sila-functional groups. Finally, the application of polysiloxanes as the precursors to ceramics, high performance coatings, and interlayer low dielectric materials are described. q 2003 Elsevier Ltd. All rights reserved. Keywords: Sila-functional oligosiloxanes; New synthetic routes; Siloxanenols; Cube; Ladder; Polysilicic acid esters; Partially silylated silicic acids; Polysilsesquioxanes; Spinnablility; Flexible free-standing films; Ceramic precursor; Coatings; Interlayer low dielectrics Contents 1. Introduction ................................................................... 000 2. Commercially available sila-functional oligosiloxanes . ................................. 000 3. Formation of siloxanes ........................................................... 000 3.1. Various oligo- and polysiloxanes ............................................... 000 3.2. Reactivity of sila-functional groups.............................................. 000 3.3. Siloxane bond formation ..................................................... 000 4. Polysiloxanes .................................................................. 000 4.1. Polysilicic acid esters and their properties ......................................... 000 4.2. Polysiloxanes capable of forming fibers and films . ................................. 000 4.3. Highly polymerized TEOS stable to self-condensation ................................ 000 4.4. Flexible free-standing films from RSi(OMe)3 ...................................... 000 4.5. Base-catalyzed hydrolytic polycondensation of RSi(OMe)3 ............................ 000 5. Linear and cyclic sila-functional oligosiloxanes ......................................... 000 5.1. Facile synthesis routes ....................................................... 000 5.1.1. Vapor phase hydrolysis................................................. 000 5.1.2. Oxidative condensation of dimethyldichlorosilane with dimethyl sulfoxide ........... 000 * Corresponding author. Tel.: þ81-4-7124-1501x3608; fax: þ81-4-7123-9890. E-mail address: [email protected] (Y. Abe). 0079-6700/03/$ - see front matter q 2003 Elsevier Ltd. All rights reserved. doi:10.1016/j.progpolymsci.2003.08.003 ARTICLE IN PRESS 2 Y. Abe, T. Gunji / Prog. Polym. Sci. xx (2004) xxx–xxx 5.1.3. Linear siloxanes with definite chain length by ring opening reaction of Dn ........... 000 5.2. IR and NMR spectra ........................................................ 000 5.3. Disiloxanols............................................................... 000 5.4. Cyclotetrasiloxane tetrols ..................................................... 000 6. Ladder oligosilsesquioxane ........................................................ 000 7. Cube siloxanes ................................................................. 000 8. Application of oligo- and polysiloxanes............................................... 000 8.1. Ceramic precursors ......................................................... 000 8.2. High performance coatings .................................................... 000 8.3. Interlayer low dielectrics for electronic devices ..................................... 000 Acknowledgements ................................................................ 000 References ....................................................................... 000 1. Introduction versatile as starting materials. The synthesis and uses of sila-functional oligosiloxanes are very limited, Polysiloxanes are versatile materials, many hav- although they can be potential building blocks for ing excellent chemical, physical, and electrical polysiloxanes and polysilsesquioxanes. The key to properties; polydimethylsiloxane is an important develop the methods for the synthesis of such example of this class of polymers. The only precursors should be the controlled reactions of disadvantage, nevertheless it is one of the excellent silanes with sila-functional groups, with special properties, of siloxanes is the fact that they are not attention to the reactivity of sila-functional groups. able to form fibers and films because of their low Subsequently, di- and trifunctional silanes would be interactions between molecules. In order to afford precursors, with hydrolysis, condensation or elimin- new functions, the structure of polysiloxanes has ation is as the preferred reactions to provide been modified by side chain functionalization or oligosiloxanes. change in the main chain. The dimension of the This review article will focus on the syntheses, macromolecular structure is a key factor in the properties, and applications of sila-functional oligo- generation of new properties: ladder and sheet are and polysiloxanes and silsesquioxanes with linear, two-dimensional structures, while cross-linked cage, cyclic, ladder, cage, and cube structures. cube, and spheres are three-dimensional structures. Such structures may find use as materials with characteristic thermal, optical, electrical, and mech- 2. Commercially available sila-functional anical properties. The state of association or oligosiloxanes aggregation of the macromolecules must also be considered. Recent research trends involve the A variety of organosilicon compounds are com- synthesis and properties of sila-functional oligo- mercially available. However, so far as oligosiloxanes and polysiloxanes, silsesquioxanes such as cage, and silsesquioxanes are concerned, very limited cube, and ladder structures, and their applications as products are available as reagents including sila- functional materials. functional oligosiloxanes and oligosilsesquioxanes Although research on siloxanes is attractive like ladder, cage, and cube. The same is also true because of the multitude of potential applications, for sila-functional silanes. Moreover, as illustrated by convenient and selective methods for the synthesis of the examples listed in Tables 1 and 2, based on sila-functional silanes and oligosiloxanes are lacking catalogues issued by several sources [1], the available Even silanes with sila-functional groups such as reagents are often expensive. R42n 2 mSi(OR)nXm or (RO)42nSiXn (m ¼ 1; 2; Sila-functional silanes R42nSiXn (n ¼ 2; 3: R ¼ n ¼ 1 , 3, R ¼ alkyl, alkenyl, aryl; X ¼ halogen, alkyl, alkenyl, aryl; X ¼ H, halogen, OR) are versatile 0 OR , OH, NR2, OCOR, NCO) are not reagents, whereas silanes R42nSiXn (n ¼ 2; 3; ARTICLE IN PRESS Y. Abe, T. Gunji / Prog. Polym. Sci. xx (2004) xxx–xxx 3 Nomenclature Mw/Mn polydispersity NMR nuclear magnetic resonance Bp boiling point ORTEP Oak Ridge thermal ellipsoid plot Bu butyl group, CH CH CH CH – 3 2 2 2 Oct octyl, (CH ) (CH ) – But tert-butyl group, (CH ) C– 3 2 2 7 3 3 PC polycarbonate D hexamethylcyclotrisiloxane, (Si(CH ) O) 3 3 2 3 PEOS polyethoxysiloxanes D octamethylcyclotetrasiloxane, 4 PET polyethylene terephthalate (Si(CH ) O) 3 2 4 PMSQ polymethylsilsesquioxane D decamethylcyclopentasiloxane, 5 PP polypropylene (Si(CH ) O) 3 2 3 PSSX partially silylated siloxane DABCO 1,4-diazabicyclo[2.2.2]octane PVSQ polyvinylsilsesquioxane DE degree of esterification Ph phenyl, C H – DS degree of silylation 6 5 Pri isopropyl, (CH ) CH– Decomp. decomposition 3 2 Qn Siloxane unit, Si(OSi ) (OR) ðn ¼ Et ethyl, CH CH – 0.5 n 42n 3 2 1–4Þ SEC size exclusion chromatography (or GPC, SOG spin-on-glass gel permeation chromatography) SUS304 stainless steel HDPE high density polyethylene TEOS tetraethoxysilane HPLC high performance liquid chromatography THF tetrahydrofuran IR spectrum infrared absorption spectrum TMOS tetramethoxysilane JIS K5400 Japan Industrial Standard No. K5400 T (5%) temperature at the weight loss of 5% MS mass spectroscopy d Tn siloxane unit, RSi(OSi ) (OR) ðn ¼ Me methyl group, CH – 0.5 n 32n 3 1–3Þ MeOH methanol Vi vinyl, CH yCH– M number average molecular weight 2 n m-CPBA meta-chloroperbenzoic acid Mp melting point d solubility parameter Mw weight average molecular weight X ¼ OH, OCOCH3,NR2, NCO) and especially Table 1. It may be noted that only siloxanes with i t (RO)42nSiXn (n ¼ 1 , 4; R ¼ Me, Et, Pr ,Bu; n ¼ 1 , 4 are commercially available, as shown at 0 X ¼ halogen, OR , OH, NR2, OCOCH3, NCO) are the bottom of Table 1. Cyclic oligodimethylsiloxanes so limited as to be supplied for commercial uses. D3,5 are the raw materials for the production of Many of them may be purchased as order-made or silicone. Usually, the only variations of the functional obtained as a component product of reaction mixtures group found with sila-functional cyclosiloxanes or a by-product.
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