Silanes

<p>Alkyl Silane - Dipodal Surface Bonding<br>Aliphatic, fluorinated aliphatic or substituted aromatic hydrocarbon substituents are the hydrophobic entities which enable silanes to induce surface hydrophobicity. The organic substitution of the silane must be non-polar. The hydrophobic effect of the organic substitution can be related to the free energy of transfer of hydrocarbon molecules from an aqueous phase to a homogeneous hydrocarbon phase. A successful hydrophobic coating must eliminate or mitigate hydrogen bonding and shield polar surfaces from interaction with water by creating a non-polar interphase. Although silane and silicone derived coatings are in general the most hydrophobic, they maintain a high degree of permeability to water vapor. This allows coatings to breathe and reduce deterioration at the coating interface associated with entrapped water. Since ions are not transported through non-polar silane and silicone coatings, they offer protection to composite structures ranging from pigmented coatings to rebar reinforced concrete. A selection guide for hydrophobic silanes can be found on pages 22-31 of the Hydrophobicity, Hydrophilicity and Silane Surface Modification brochure.<br>Non Functional Alkoxy Silane<br>Silane coupling agents have the ability to form a durable bond between organic and inorganic materials to generate desired heterogeneous environments or to incorporate the bulk properties of different phases into a uniform composite structure. The general formula has two classes of functionality. The hydrolyzable group forms stable condensation products with siliceous surfaces and other oxides such as those of aluminum, zirconium, tin, titanium, and nickel. The organofunctional group alters the wetting or adhesion characteristics of the substrate, utilizes the substrate to catalyze chemical transformations at the heterogeneous interface, orders the interfacial region, or modifies its partition characteristics, and significantly effects the covalent bond between organic and inorganic materials.<br>Dipodal Silane<br>Dipodal silanes are a series of adhesion promoters that have intrinsic hydrolytic stabilities up to ~10,000 times greater than conventional silanes and are used in applications such as plastic optics, multilayer printed circuit boards and as adhesive primers for ferrous and nonferrous metals. They have the ability to form up to six bonds to a substrate compared to conventional silanes with the ability to form only three bonds to a substrate. Many conventional coupling agents are frequently used in combination with 10-40% of a non-functional dipodal silane, where the conventional coupling agent provides the appropriate functionality for the application, and the non-functional dipodal silane provides increased durability. Also known as bis-silanes additives enhance hydrolytic stability, which impacts on increased product shelf life, ensures better substrate bonding and also leads to improved mechanical properties in coatings as well as composite applications.<br>1-(Triethoxysilyl)-2-(diethoxymethylsilyl)ethane<br>Forms abrasion resistant sol-gel coatingsLower toxicity, easier to handle than bis(triethoxysilyl)ethane, SIB1817.0Improves hydrolytic stability of silane adhesion promotion systemsUsed in surface modification<br></p>

<p>2-(3,4-Epoxycyclohexyl)ethyltriethoxysilane;(2-triethoxysilylethyl)cyclohexyloxirane<br>Epoxy functional trialkoxy silaneAdhesion promoter for water-borne coatings on alkaline substratesUsed in microparticle surface modificationCoupling agent for UV cure and epoxy systemsEpoxy silane treated surfaces convert to hydrophilic-diols when exposed to moisture<br></p>

<p>Specialty Silicon-Based Blocking Agent<br>Used as a protecting group for reactive hydrogens in alcohols, amines, thiols, and carboxylic acids. Organosilanes are hydrogen-like, can be introduced in high yield, and can be removed under selective conditions. They are stable over a wide range of reaction conditions and can be removed in the presence of other functional groups, including other protecting groups. The tolerance of silylated alcohols to chemical transformations summary is presented in Table 1 of the Silicon-Based Blocking Agents brochure.<br>Alkyl Silane - Conventional Surface Bonding<br>Aliphatic, fluorinated aliphatic or substituted aromatic hydrocarbon substituents are the hydrophobic entities which enable silanes to induce surface hydrophobicity. The organic substitution of the silane must be non-polar. The hydrophobic effect of the organic substitution can be related to the free energy of transfer of hydrocarbon molecules from an aqueous phase to a homogeneous hydrocarbon phase. A successful hydrophobic coating must eliminate or mitigate hydrogen bonding and shield polar surfaces from interaction with water by creating a non-polar interphase. Although silane and silicone derived coatings are in general the most hydrophobic, they maintain a high degree of permeability to water vapor. This allows coatings to breathe and reduce deterioration at the coating interface associated with entrapped water. Since ions are not transported through non-polar silane and silicone coatings, they offer protection to composite structures ranging from pigmented coatings to rebar reinforced concrete. A selection guide for hydrophobic silanes can be found on pages 22-31 of the Hydrophobicity, Hydrophilicity and Silane Surface Modification brochure.<br>Bis(trimethylsiloxy)dichlorosilane; 3,3-Dichlorohexamethyltrisiloxane<br>Sterically-hindered for the protection of diolsSummary of selective deprotection conditions is provided in Table 7 through Table 20 of the Silicon-Based Blocking Agents brochure<br></p>

<p>n-Butylaminopropyltrimethoxysilane; N-[3-(trimethoxysilyl)propyl]butylamine; N-[3-(trimethoxysilyl)propyl]-n-butylamine<br>Secondary amino functional trialkoxy silaneReacts with isocyanate resins to form urethane moisture cureable systemsUsed in microparticle surface modificationInternal secondary amine coupling agent for UV cure and epoxy systemsAdvanced cyclic analog available: SIB1932.4<br></p>

<p>Halogen Functional Trialkoxy Silane<br>Silane coupling agents have the ability to form a durable bond between organic and inorganic materials to generate desired heterogeneous environments or to incorporate the bulk properties of different phases into a uniform composite structure. The general formula has two classes of functionality. The hydrolyzable group forms stable condensation products with siliceous surfaces and other oxides such as those of aluminum, zirconium, tin, titanium, and nickel. The organofunctional group alters the wetting or adhesion characteristics of the substrate, utilizes the substrate to catalyze chemical transformations at the heterogeneous interface, orders the interfacial region, or modifies its partition characteristics, and significantly effects the covalent bond between organic and inorganic materials.<br>3-Chloropropyltrimethoxysilane; 1-Chloro-3-(trimethoxysilyl)propane<br>Viscosity, 20 °: 0.56 cStγc of treated surfaces: 40.5 mN/mSpecific wetting surface: 394 m2/gVapor pressure, 100 °C: 40 mmAdhesion promoter for styrene-butadiene rubber, SBR, hot-melt adhesivesPowder flow control additive for dry powder fire extinguishing media<br></p>

<p>Bridging Silicon-Based Blocking Agent<br>Used as a protecting group for reactive hydrogens in alcohols, amines, thiols, and carboxylic acids. Organosilanes are hydrogen-like, can be introduced in high yield, and can be removed under selective conditions. They are stable over a wide range of reaction conditions and can be removed in the presence of other functional groups, including other protecting groups. The tolerance of silylated alcohols to chemical transformations summary is presented in Table 1 of the Silicon-Based Blocking Agents brochure.<br>Alkyl Silane - Conventional Surface Bonding<br>Aliphatic, fluorinated aliphatic or substituted aromatic hydrocarbon substituents are the hydrophobic entities which enable silanes to induce surface hydrophobicity. The organic substitution of the silane must be non-polar. The hydrophobic effect of the organic substitution can be related to the free energy of transfer of hydrocarbon molecules from an aqueous phase to a homogeneous hydrocarbon phase. A successful hydrophobic coating must eliminate or mitigate hydrogen bonding and shield polar surfaces from interaction with water by creating a non-polar interphase. Although silane and silicone derived coatings are in general the most hydrophobic, they maintain a high degree of permeability to water vapor. This allows coatings to breathe and reduce deterioration at the coating interface associated with entrapped water. Since ions are not transported through non-polar silane and silicone coatings, they offer protection to composite structures ranging from pigmented coatings to rebar reinforced concrete. A selection guide for hydrophobic silanes can be found on pages 22-31 of the Hydrophobicity, Hydrophilicity and Silane Surface Modification brochure.<br>Diethyldichlorosilane; Dichlorodiethylsilane; DES<br>ΔHvap: 41.9 kJ/molDipole moment: 2.4 debyeSurface tension: 30.3 mN/mVapor pressure, 21 °C: 10 mmThermal conductivity: 0.134 W/m°CSimilar to, but more stable derivatives than dimethylsilylenesSummary of selective deprotection conditions is provided in Table 7 through Table 20 of the Silicon-Based Blocking Agents brochure<br></p>

<p>Alkyl Silane - Conventional Surface Bonding<br>Aliphatic, fluorinated aliphatic or substituted aromatic hydrocarbon substituents are the hydrophobic entities which enable silanes to induce surface hydrophobicity. The organic substitution of the silane must be non-polar. The hydrophobic effect of the organic substitution can be related to the free energy of transfer of hydrocarbon molecules from an aqueous phase to a homogeneous hydrocarbon phase. A successful hydrophobic coating must eliminate or mitigate hydrogen bonding and shield polar surfaces from interaction with water by creating a non-polar interphase. Although silane and silicone derived coatings are in general the most hydrophobic, they maintain a high degree of permeability to water vapor. This allows coatings to breathe and reduce deterioration at the coating interface associated with entrapped water. Since ions are not transported through non-polar silane and silicone coatings, they offer protection to composite structures ranging from pigmented coatings to rebar reinforced concrete. A selection guide for hydrophobic silanes can be found on pages 22-31 of the Hydrophobicity, Hydrophilicity and Silane Surface Modification brochure.<br>n-Octadecyldimethylchlorosilane; Dimethyl-n-octadecylchlorosilane; Chlorodimethyloctadecylsilane; Chlorodimethylsilyl-n-octadecane<br>Contains 5-10% C18 isomersEmployed in bonded HPLC reverse phases<br></p>

<p>Alkenylsilane Cross-Coupling Agent<br>The cross-coupling reaction is a highly useful methodology for the formation of carbon-carbon bonds. It involves two reagents, with one typically being a suitable organometallic reagent - the nucleophile - and the other a suitable organic substrate, normally an unsaturated halide, tosylate or similar - the electrophile.<br>Vinyltrimethylsilane; Ethenyltrimethylsilane; Trimethylsilylethene; Trimethylvinylsilane<br>Viscosity, 20 °C: 0.5 cStΔHcomb: 4,133 kJ/molΔHfus: 7.7 kJ/molCopolymerization parameters- e,Q: 0.04, 0.029Forms polymers which can be fabricated into oxygen enrichment membranesPolymerization catalyzed by alkyllithium compoundsReacts w/ azides to form trimethylsilyl-substituted aziridinesUndergoes Heck coupling to (E)-β-substituted vinyltrimethylsilanes, which can then be cross-coupled furtherExtensive review of silicon based cross-coupling agents: Denmark, S. E. et al. "Organic Reactions, Volume 75" Denmark, S. E. ed., John Wiley and Sons, 233, 2011<br></p>

<p>Mixed m-, p-isomers<br></p>

<p>(N,N-Dimethyl-3-aminopropyl)trimethoxysilane; N-(3-trimethoxysilyl)propyl-N,N-dimethylamine<br>Tertiary amino functional trialkoxy silaneDerivatized silica catalyzes Michael reactions<br></p>

<p>Alkyl Silane - Conventional Surface Bonding<br>Aliphatic, fluorinated aliphatic or substituted aromatic hydrocarbon substituents are the hydrophobic entities which enable silanes to induce surface hydrophobicity. The organic substitution of the silane must be non-polar. The hydrophobic effect of the organic substitution can be related to the free energy of transfer of hydrocarbon molecules from an aqueous phase to a homogeneous hydrocarbon phase. A successful hydrophobic coating must eliminate or mitigate hydrogen bonding and shield polar surfaces from interaction with water by creating a non-polar interphase. Although silane and silicone derived coatings are in general the most hydrophobic, they maintain a high degree of permeability to water vapor. This allows coatings to breathe and reduce deterioration at the coating interface associated with entrapped water. Since ions are not transported through non-polar silane and silicone coatings, they offer protection to composite structures ranging from pigmented coatings to rebar reinforced concrete. A selection guide for hydrophobic silanes can be found on pages 22-31 of the Hydrophobicity, Hydrophilicity and Silane Surface Modification brochure.<br>n-Octyldimethyl(dimethylamino)silane; Dimethylaminooctyldimethylsilane<br></p>

<p>Bridging Silicon-Based Blocking Agent<br>Used as a protecting group for reactive hydrogens in alcohols, amines, thiols, and carboxylic acids. Organosilanes are hydrogen-like, can be introduced in high yield, and can be removed under selective conditions. They are stable over a wide range of reaction conditions and can be removed in the presence of other functional groups, including other protecting groups. The tolerance of silylated alcohols to chemical transformations summary is presented in Table 1 of the Silicon-Based Blocking Agents brochure.<br>Alkyl Silane - Conventional Surface Bonding<br>Aliphatic, fluorinated aliphatic or substituted aromatic hydrocarbon substituents are the hydrophobic entities which enable silanes to induce surface hydrophobicity. The organic substitution of the silane must be non-polar. The hydrophobic effect of the organic substitution can be related to the free energy of transfer of hydrocarbon molecules from an aqueous phase to a homogeneous hydrocarbon phase. A successful hydrophobic coating must eliminate or mitigate hydrogen bonding and shield polar surfaces from interaction with water by creating a non-polar interphase. Although silane and silicone derived coatings are in general the most hydrophobic, they maintain a high degree of permeability to water vapor. This allows coatings to breathe and reduce deterioration at the coating interface associated with entrapped water. Since ions are not transported through non-polar silane and silicone coatings, they offer protection to composite structures ranging from pigmented coatings to rebar reinforced concrete. A selection guide for hydrophobic silanes can be found on pages 22-31 of the Hydrophobicity, Hydrophilicity and Silane Surface Modification brochure.<br>Hexamethylcyclotrisilazane; Hexamethylcyclotrisilazane; 2,2,4,4,6,6-Hexamethylcyclotrisilazane<br>Viscosity, 20 °C: 1.7 cStΔHform: 553 kJ/molDielectric constant: 1000Hz: 2.57Dipole moment: 0.92 debyePolymerizes to polydimethylsilazane oligomer in presence of Ru/H2Modifies positive resists for O2 plasma resistanceSilylates diols with loss of ammoniaSimilar in reactivity to HMDS, SIH6110.0Summary of selective deprotection conditions is provided in Table 7 through Table 20 of the Silicon-Based Blocking Agents brochure<br></p>

<p>Trialkylsilyl Blocking Agent<br>Used as a protecting group for reactive hydrogens in alcohols, amines, thiols, and carboxylic acids. Organosilanes are hydrogen-like, can be introduced in high yield, and can be removed under selective conditions. They are stable over a wide range of reaction conditions and can be removed in the presence of other functional groups, including other protecting groups. The tolerance of silylated alcohols to chemical transformations summary is presented in Table 1 of the Silicon-Based Blocking Agents brochure.<br>Triethylchlorosilane; Chlorotriethylsilane; TES-Cl<br>Stability of ethers intermediate between TMS and TBS ethersGood for 1°, 2°, 3° alcoholsCan be cleaved in presence of TBS, TIPS and TBDPS ethersUsed primarily for the protection of alcoholsCan be used to protect amines and carboxylic acidsSummary of selective deprotection conditions is provided in Table 7 through Table 20 of the Silicon-Based Blocking Agents brochure<br></p>

<p>Phenyl-Containing Blocking Agent<br>Used as a protecting group for reactive hydrogens in alcohols, amines, thiols, and carboxylic acids. Organosilanes are hydrogen-like, can be introduced in high yield, and can be removed under selective conditions. They are stable over a wide range of reaction conditions and can be removed in the presence of other functional groups, including other protecting groups. The tolerance of silylated alcohols to chemical transformations summary is presented in Table 1 of the Silicon-Based Blocking Agents brochure.<br>Aromatic Silane - Conventional Surface Bonding<br>Aliphatic, fluorinated aliphatic or substituted aromatic hydrocarbon substituents are the hydrophobic entities which enable silanes to induce surface hydrophobicity. The organic substitution of the silane must be non-polar. The hydrophobic effect of the organic substitution can be related to the free energy of transfer of hydrocarbon molecules from an aqueous phase to a homogeneous hydrocarbon phase. A successful hydrophobic coating must eliminate or mitigate hydrogen bonding and shield polar surfaces from interaction with water by creating a non-polar interphase. Although silane and silicone derived coatings are in general the most hydrophobic, they maintain a high degree of permeability to water vapor. This allows coatings to breathe and reduce deterioration at the coating interface associated with entrapped water. Since ions are not transported through non-polar silane and silicone coatings, they offer protection to composite structures ranging from pigmented coatings to rebar reinforced concrete. A selection guide for hydrophobic silanes can be found on pages 22-31 of the Hydrophobicity, Hydrophilicity and Silane Surface Modification brochure.<br>Diphenylmethylchlorosilane; Methyldiphenylchlorosilane; Chloro(methyl)diphenylsilane<br>Viscosity: 5.3 cStΔHvap: 623.7 kJ/molSurface tension: 40.0 mN/mVapor pressure, 125 °C: 3 mmThermal conductivity: 0.112 W/m°Cα-Silylates esters, lactones; precursors to silyl enolatesC-Silylates carbamates as shown in the enantioselective example w/ a neryl carbamateStability versus other silyl ethers studiedSummary of selective deprotection conditions is provided in Table 7 through Table 20 of the Silicon-Based Blocking Agents brochure<br></p>