Novel polymer systems with very bulky organosilicon side chain substituents

Kowalewska, Anna; Stańczyk, Włlodzimierz A.; Boileau, Sylvie; Lestel, Laurence; Smith, J. David

doi:10.1016/s0032-3861(98)00222-5

Cited by 45 publications

(30 citation statements)

References 13 publications

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“…8,9 Correspondenceto:M.D.Guiver(E-mail:michael.guiver@ nrc.ca) Polymeric materials with bulky silicon side groups result in significant changes in polymer properties such as gas permeability and permselectivity; mechanical, thermal and surface properties; and photochemical reactivity. 10 Polymers containing silicon substituents either in the main chain or attached as side groups are of particular interest for gas-separation membranes because of their potential ability to hinder chain motions and to disrupt chain packing, thereby improving gas permeability with minimal loss in selectivity.…”

Section: Introductionmentioning

confidence: 99%

Modified polysulfones. IV. Synthesis and characterization of polymers with silicon substituents for a comparative study of gas‐transport properties

Guiver¹,

Robertson²,

Rowe³

et al. 2001

J. Polym. Sci. A Polym. Chem.

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Wepreviouslyconductedadetailedstudyofgas-transportandotherpropertiesofaseriesofsiliconderivativesofUdelpolysulfone(PSf)andRadelpolyphenylsulfone;wenowreportthedetailsoftheirpreparationbythereactionoflithiated polymerintermediateswithchlorosilylalkylarylelectrophiles.Ortho-sulfone-substitutedpolymerswithpendanttrimethylsilyl,dimethylphenylsilyl,anddiphenylmethylsilylandothergroupswereobtainedbydirectmetalationfollowedbythereactionofthe dilithiatedintermediatewiththeappropriatesilylelectrophile.Inaddition,thestructuralregularityandgeometryofthedilithiatedsitewasalsoexploitedtointroduce siliconintothemainchainbythereactionofdichlorosilylelectrophiles,leadingtothe formationofanewtricyclicheteroatomring.Ortho-etherPSfderivativeswereobtained fromadibrominatedpolymerviathelithiationofbrominatedpolymerandreaction withasilylelectrophile.Thedegreeofsubstitutionofthesilylgroupswas2.0orless fromdilithiatedpolymersandwasdependentontheelectrophilereactivityandreaction conditions.AdetailedstructuralcharacterizationofthepolymersbyNMRandIRspectroscopyisreportedinadditiontoglass-transitiontemperaturesandthermalstabilities.

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Section: Introductionmentioning

confidence: 99%

Modified polysulfones. IV. Synthesis and characterization of polymers with silicon substituents for a comparative study of gas‐transport properties

Guiver¹,

Robertson²,

Rowe³

et al. 2001

J. Polym. Sci. A Polym. Chem.

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“…The attachment of the organosilyl groups to the macromolecular chain should lead to important modification of the polymer properties, such as gas permeability and permselectivity parameters, mechanical, thermal and surface properties, as well as photochemical reactivity [1,8]. Reports in the literature express some interest in this area, as a number of polymers, modified by silyl groups of various steric bulk, were synthesized and their properties studied [9][10][11][12][13].…”

Section: Resultsmentioning

confidence: 99%

“…The preparation of polymers containing very bulky tris(trimethylsilyl)methyl groups with three organosilyl substituents bound to the central carbon atom is a new and interesting field in polymer and silicon chemistry [8]. We herein report the synthesis and properties of new polysiloxanes containing 3-(2,3-epoxypropoxy)propyl(EP-PMS) and chloromethyl phenethyl groups (ClPh-PMS) by hydrosilylation of allyl glycidyl ether (AGE) and chloromethyl styrene (CMS) each with polymethylsiloxane (PMS), followed by the attachment of Tsi groups to the resulting polymers by the reaction between tris(trimethylsilyl)methyl lithium (TsiLi) and epoxide or benzyl chloride groups.…”

Section: Introductionmentioning

confidence: 99%

Trisyl modification of epoxy- and chloromethyl-polysiloxanes

Safa

Bahadori

Tofangdarzadeh

et al. 2008

JICS

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The new bulky organosilicon compound HC(Me 2 SiCH 2 CH 2 CH 2 OCH 2 CycloCHCH 2 O) 3 was synthesized by hydrosilylation of tris(dimethylsilyl)methane (HMe 2 Si) 3 CH and allyl glycidyl ether (AGE) in the presence of H 2 PtCl 6 as a catalyst. Polysiloxanes containing 3-(2,3-epoxypropoxy)propyl and chloromethylphenethyl groups were synthesized by hydrosilylation of AGE and chloromethyl styrene (CMS) with hydrogen-containing polymethylsiloxane (PMHS). Both types of polymers could be modified by incorporation of the highly sterically-demanding tris(trimethylsilyl)methyl [trisyl = (Me 3 Si) 3 C] substituent. The trisyl (Tsi) groups were attached to the obtained polymers as side chains by reacting excess trisyl lithium with benzyl chloride and epoxy groups. The epoxy groups possess a higher reactivity for TsiLi than the chloromethyl groups. The ring opening reaction between the epoxy groups and TsiLi is fast. The modification increases the rigidity of the polymers as shown by differential scanning calorimetry analysis. The incorporation of the Tsi groups into the polymer structure creates macromolecules of novel architecture with potential use as membranes for fluid separation. All the resulting polymers were characterized by FT-IR and 1 H NMR spectroscopy.

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“…In the literature, there are examples of some interesting polymers that were modified by silyl groups [8 -10]. Attaching silyl groups to macromolecular chains leads to important modifications of polymer properties, such as mechanical, thermal and surface properties, as well as photochemical reactivity [11]. On the other hand, some silyl derivatives of polymers such as styrene showed membrane properties.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of new monomer and polymers of hindered silyl styrene

Assadi

Golipour

2007

Designed Monomers and Polymers

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Abstract-In this paper we report the synthesis of a new hindered organosilicon derivative of styrene monomer, homo-polymer and co-polymers. This new monomer was synthesized from reaction of the lithiated derivative of para-methyl styrene with tris(trimethylsilyl)silylchloride in room temperature. Homo-polymerization or co-polymerization was done using a free radical polymerization method using α,α -azobis(isobutyronitrile) (AIBN) as a initiator. Incorporation of this bulky group to polymers showed a high glass transition temperature compared to polystyrene without this group. Monomer and polymers and compositions of poly(para-sisylmethylstyrene) in co-polymers was characterized by spectroscopy. Since, some important polymer properties have been modified by incoporating silyl groups, this work can be an important case in polymer chemistry.

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Novel polymer systems with very bulky organosilicon side chain substituents

Cited by 45 publications

References 13 publications

Modified polysulfones. IV. Synthesis and characterization of polymers with silicon substituents for a comparative study of gas‐transport properties

Modified polysulfones. IV. Synthesis and characterization of polymers with silicon substituents for a comparative study of gas‐transport properties

Trisyl modification of epoxy- and chloromethyl-polysiloxanes

Synthesis and characterization of new monomer and polymers of hindered silyl styrene

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