Silylation of triacylglycerol: an easy route to new biosiloxanes

Kadib, Abdelkrim El; Castel, Annie; Delpech, Fabien; Rivière, P.

doi:10.1016/j.chemphyslip.2007.05.002

Cited by 14 publications

(19 citation statements)

References 39 publications

(42 reference statements)

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“…The surfaces were prepared by grafting a natural phospholipid precursor bearing unsaturated fatty chains to PMHS films on glass or silicon. Additionally, very few studies have reported the hydrosilylation of unsaturated fatty acid derivatives [27,[63][64][65][66][67][68][69][70]. The catalytic hydrosylilation process to PMHS films gave surfaces of high densities of phospholipid 6 that are highly hydrophilic and strongly resistant to several proteins [61,62] (fibrinogen adsorption < 5 ng/cm 2 ) in comparison with other zwitterionic materials (sulfobetaine, carboxybetaine) [71,72].…”

Section: Introductionmentioning

confidence: 99%

Controlled structure and hydrophilic property of polymethylhydrosiloxane thin films attached on silicon support and modified with phosphorylcholine group

2020

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Thin films of crosslinked polymethylhydrosiloxane (PMHS) are grafted on silica using sol-gel process allowing subsequent coupling of molecules by hydrosilylation grafting to Si-H groups.The aim was to fabricate stable polysiloxane film on solid supports with well-characterized functionalities and surface properties for various applications. The pristine PMHS surface was modified with phosphorylcholine group by reaction at room temperature or 40 °C catalyzed by Karsted's catalyst with a phospholipid molecule containing linoleoyl chains to form hydrophilic surfaces as a model. The purpose was to characterize precisely the structure and composition of virgin and treated PMHS films in relation with the wetting properties by using IR and X-ray photoelectron spectroscopies (XPS). The surface properties were studied by pure water contact *Manuscript Click here to view linked References 2 angle measurements in air by using sessile drops and captive bubbles, atomic force microscopy, and scanning electron microscopy. The modified surfaces are highly hydrophilic with contact angle varying from 40 to 0°. Analysis of the composition of the surface showed that the reaction of linoleoyl chains gives the 2:1 (Si:phospholipid) hydrosilylation adducts resultant from one fold addition of methylhydrosilane on each linoleoyl chain. The graft yield in terms of molecular percentage determined by XPS in various conditions was correlated in good agreement with wetting properties and previous protein adsorption measurements for comparison purpose.

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Section: Introductionmentioning

confidence: 99%

Controlled structure and hydrophilic property of polymethylhydrosiloxane thin films attached on silicon support and modified with phosphorylcholine group

2020

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“…Recently, El Kadib et al [48] showed for a silylation reaction that there were two forms of silylated product (i.e. O-and C-silyl forms.…”

Section: Silylation Of Yttrium Triacetatementioning

confidence: 99%

Two synthesis routes of organometallic precursors for the elaboration of SiCNYO pre‐alloyed nanopowders

Chehaidi

Foucaud

Maı̂tre

et al. 2010

Applied Organom Chemis

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International audienceTwo routes were simultaneously investigated to prepare organometallic precursors. They were characterized by NMR and FTIR techniques. In the first route, yttrium acetate was silylated by trimethylchlorosilane before its dissolution in hexamethydisilazane. That leads to a liquid precursor containing Si–C–N–Y–O–H elements. In the second route, a precursor with the same elements was elaborated by dissolution of an amminolysed yttrium compound in tetramethyldisiloxane. The amminolysed yttrium compound was obtained through the amminolysis of the yttrium trichloride by triethylamine [N(C2H5)3]

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“…[15,16] Amine functional groups have been targeted with the goal of reaching hardeners for bio-based epoxy resins. [22,23] Creation of a Si-modified bio-based oil involves attaching silane groups to a previously epoxidized natural oil via an aminosilane molecule, such as 3-aminopropyltriethoxysilane (APTES). [4,17,[19][20][21] The insertion of elements such as silicon and titanium is a very interesting way to modify vegetable oils, since it opens the way to cross-link oils through the sol-gel process.…”

Section: Introductionmentioning

confidence: 99%

“…The insertion of elements such as silicon and titanium is a very interesting way to modify vegetable oils, since it opens the way to cross‐link oils through the sol‐gel process. The catalyzed hydrosilylation of vegetable oils has been explored to reach mesoporous materials and biosiloxanes . Creation of a Si‐modified bio‐based oil involves attaching silane groups to a previously epoxidized natural oil via an aminosilane molecule, such as 3‐aminopropyltriethoxysilane (APTES) .…”

Section: Introductionmentioning

confidence: 99%

Preparation and Spectroscopic Characterization of Si‐Coated Vegetable Oils and their Application in In Situ Curing of Hybrid Coatings

Maurin‐Pasturel

Lemor²,

Robin

et al. 2019

Euro J Lipid Sci & Tech

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The modification of natural oils with heteroatoms leads to materials that can be employed in various areas thanks to their specific properties. Here, a solventless chemical modification of epoxidized linseed oil with an aminosilane without a catalyst is developed, and a detailed study of the chemical reactions involved during the process is reported. The mechanism results in two competitive reactions: the ring‐opening of epoxides and trans‐amidification of triglycerides with the amine functional group of aminosilane. These competitive reactions are shown by infrared spectroscopy (FTIR) and 1H, 13C, and 2D nuclear magnetic resonance (NMR). Even if the epoxy ring‐opening remains the major route, the trans‐amidification cannot be ignored. These modified oils are very reactive under atmospheric conditions by cross‐linking according to a polycondensation of the −Si(OMe)3 moieties or via a sol‐gel process and lead to a rapid hardening. The final material gives hydrophobic and glossy coatings on cellulose and glass. Practical Applications: This paper details the easy route to convert vegetable oils into coatings by crosslinking under mild conditions. These bio‐based materials can be applied as oil‐based impregnating products for exterior wood protection and in the hydrophobization of paper. Epoxidized linseed oil is chemically modified with an amino silane to make it reactive under atmospheric conditions. The chemical reaction is detailed and side reactions identified. Polycondensation of the grafted alkoxysilanes leads to hydrophobic coatings on cellulose and glass.

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Silylation of triacylglycerol: an easy route to new biosiloxanes

Cited by 14 publications

References 39 publications

Controlled structure and hydrophilic property of polymethylhydrosiloxane thin films attached on silicon support and modified with phosphorylcholine group

Controlled structure and hydrophilic property of polymethylhydrosiloxane thin films attached on silicon support and modified with phosphorylcholine group

Two synthesis routes of organometallic precursors for the elaboration of SiCNYO pre‐alloyed nanopowders

Preparation and Spectroscopic Characterization of Si‐Coated Vegetable Oils and their Application in In Situ Curing of Hybrid Coatings

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