Synthesis of Condensation Polymers Derived From Silylated Monomers Under Phase Transfer Catalysis

Lembach

2010

J. Chil. Chem. Soc.

This work describes the synthesis of aliphatic diacids and diamines containing a silarylene moiety in the structure. These compounds can be employed as monomers for the synthesis of poly(amides) and poly(esters) or other condensation polymers. Thus, bis(p-methylphenylen)(R)phenylsilanes were obtained from p-bromotoluene and dicloro(R)phenylsilane (R= Me, Ph). Also, the dibenzyl nitrile compounds bis(p-(cyanomethyl)phenylen)(R)phenylsilanes were synthesized from the respective bis(p-(bromomethyl)phenylen) (R)phenylsilanes derivatives. The hydrolysis of the dibenzyl nitrile derivatives gives the respective diacids bis(p-(carboxymethyl)phenylen)(R)phenylsilanes with low yield. A direct Grignard reaction type was also studied using as precursors the dibenzyl bromide compounds. In a second stage, the synthesis of the phenethylamine bis(p-(2-aminoethyl)phenylen)(R)phenylsilane was studied by the reduction of the dibenzyl nitrile compounds. All compounds were characterized by IR-TF, 1 H, 13 C and 29 Si NMR.

Section: Resultsmentioning

confidence: 99%

Section: Bis(p-methylphenylen)(r)phenylsilanes (1)mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

DIFUNCTIONAL SILARYLENE-CONTAINING ALIPHATIC COMPOUNDS: SYNTHESIS AND CHARACTERIZATION OF BIS(p (CARBOXYMETHYL)PHENYL)(R)PHENYLSILANE AND BIS(p-(2-AMINOETHYL)PHENYL)(R)PHENYLSILANE (R = Me, Ph)

Lembach

2010

J. Chil. Chem. Soc.

“…12,19 The diacids, bis(4-carboxyphenyl) dimethylsilane (2a) and bis(4-carboxyphenyl)ethylmethylsilane (2b), were obtained by oxidation of the ditolyl compounds, according to a described procedure. 15 These diacids were reduced with LiAlH 4 in THF in order to obtain the dialcohols bis(4-hydroxymethylphenyl)dimethylsilane (3a) or bis(4-hydroxymethylphenyl)ethylmethylsilane (3b), according to the procedure described by Mingal et al 15 All compounds were characterized by FT-IR and 1 H, 13 C and 29 Si NMR spectroscopy, and the results were in agreement with the proposed structures.…”

Section: Precursors and Monomers Synthesismentioning

confidence: 99%

“…2,[10][11][12][13] Likewise, it has been reported the preparation of polycondensation materials that include the ester and other functional groups. 4,6,14 On the other hand, Migdal et al 15 reported the synthesis of a series of dimethylsilylen-containing aliphatic poly(esters).…”

Section: Introductionmentioning

confidence: 99%

Silicon-Containing Aromatic Poly(esters) Derived From Bis(4-Carboxyphenyl)methyl-R-Silane and Bis(4-(Hydroxymethyl) Phenyl)methyl-R-Silane: Synthesis, Characterization and Thermal Studies

Pino

2012

J. Chil. Chem. Soc.

This work describes the synthesis, characterization and thermal studies of poly(esters) (PEs) containing two Si atoms in the main chain, derived from aromatic diacids and aliphatic dialcohols in which the Si atom is bonded to methyl and/or ethyl groups. PEs were characterized by FT-IR and 1 H, 13 C and 29 Si spectroscopy and the results were in agreement with the proposed structures. Poly(esters) were soluble in polar aprotic solvents, such as DMSO and DMF, and acetone, and partially soluble in ethanol. The inherent viscosity and glass transition and thermal decomposition temperatures, h inh , Tg and TDT respectively, were determined. These results showed that PE-2 and PE-4, derived from the dialcohol with the -Si(CH 3 )(CH 2 CH 3 )-moiety as central element, had the larger values of h inh , Tg, TDT and the residual weight after heating at 900 °C, indicating that the specific structure of aliphatic dialcohols control the reaction.

Poly(amides) and poly(imides) containing silicon and germanium in the main chain: Synthesis, characterization and thermal studies

J of Applied Polymer Sci

Leiva

et al. 2006

Poly(amides) and poly(imides) containing the heteroatoms Si or Ge in the main chain and bonded to four carbon atoms were synthesized and characterized by IR and 1 H, 13 C and 29 Si NMR. The acid dichlorides bis(4-chloroformylphenyl)-dimethylgermane, bis(4-chloroformylphenyl)-diphenylgermane, bis(4-chloroformylphenyl)-dimethylsilane, and bis(4-chloroformylphenyl)-diphenylsilane were synthesized from the ditolyl derivatives, which were oxidized to the respective diacids. The dianhydrides bis(3,4-dicarboxyphenyl)-dimethylgermane dianhydride, bis(3,4-dicarboxyphenyl)-diphenylgermane dianhydride, bis(3,4-dicarboxyphenyl)-dimethylsilane dianhydride, and bis(3,4-dicarboxyphenyl)-diphenylsilane dianhydride were synthesized from the dixylyl derivatives, which were oxidized to the tetraacids. Fully aromatic diamines also containing Si or Ge were synthesized from 4-bromo-N,N-bis(trimethylsilyl)-aniline and diphenyl-dichlorosilane or germane. The ditolyl and dixylyl derivatives were synthesized from 4-bromo-toluene or 4-bromo-xylene and dimethyl-or diphenyl-dichlorogermane, dimethyl-or diphenyl-dichlorosilane. The glass transition temperatures and the thermal stability were determined showing in general that the polymers with Si atom in the main chain presented higher values of both parameters due to the higher ionic character of the CÀ ÀSi bond compared with the CÀ ÀGe one, and due to the lower size of the Si atom that presents lower rotational barriers.