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SILANES I ORGANOFUNCTIONAL
3
Organofunctional silanes –
Organic X Si OR HO Inorganic
polymer substrate
X Si O
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MOLECULAR BRIDGES FORGE
STABLE BONDS
Fig. 2: Adhesion promotion Fig. 3: Surface modification Fig. 4: Crosslinking
R X
X X X O O
O O
O O O Si
O X
Si O Si
HO Si O Si O Si OH O Si O O
O O O Si HO Si
OR
X
X
X
X
Substrate Polymer Polymer
Organofunctional silanes enhance adhe- Organofunctional silanes improve com- Organofunctional silanes function as
sion of coatings, adhesives and sealants patibility and enable inorganic fillers to crosslinkers for organic polymers, e. g. in
to a wide variety of substrates. bond chemically to organic resins. moisture-curing adhesives and sealants,
in paints and varnishes and in thermo-
plastics.
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CHEMICAL BONDING TO
ORGANIC POLYMERS
The particular function and the nature Fig. 5: Endcapping
of the organic polymer will determine
the choice of silane as well as the way
in which it bonds chemically to the
polymer.
Vinyl- or methacryloxysilane
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Fig. 7: Copolymerization Table 1: Compatibility of polymers and organofunctional silanes
Polymer Organofunctional group on silane
Polyacrylate Amino
C CH2 C CH2
Epoxy
Methacrylic
CO2R Vinyl
Si Butyl rubber, neoprene, phenolic resin, Amino
Vinyl- or
Acrylate/ methacryl- polyamide, polyether, epoxy resin, melamine Epoxy
methacrylate oxysilane Polyester Methacrylic
Polyolefin Amino
Vinyl
C CH2 C CH2 Polysulfide Epoxy
Vinyl
CO2R Polyurethane Amino
Epoxy
Si Isocyanate
EPR, EPDM, SBR Vinyl, Mercapto
Radical Grafting
Copolymerization
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THE LENGTH OF THE BRIDGE DETERMINES
THE REACTIVITY – The “α EFFEcT“
The nature of the “bridge construction” Fig. 8 Fig. 10
determines the application proper-
ties. a-Silanes, that is, silanes with a OR OR
methylene bridge instead of the usual
propylene spacer between the silicon X (CH2)3 Si OR X CH2 Si OR
atom and the functional group, are
highly reactive and accordingly have OR OR
huge application potential.
Fig. 9 Fig. 11
CH3 CH3
X (CH2)3 Si OR X CH2 Si OR
OR OR
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Fig. 12: Schematic diagram of the “a effect” Practical Consequences of the
“a Effect”
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Hydrolysis of Unsaturated Silanes Fig. 13: Rate of hydrolysis of unsaturated silanes (acetone/water mixture, pH 4)
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Fig. 14: Skin-formation times of silane-terminated polyethers in adhesive formulations The key advantages of GENIOSIL®
a-silanes are:
Skin-formation times
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GENIOSIL ® FOR
ADHESIVES AND SEALANTS
Silane crosslinking is a key technology
for state-of-the-art adhesives and
sealants. GENIOSIL® a-silanes offer
unforeseen advantages.
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For highly reactive adhesive and sealant
systems, such as the a-silane-cross-
linking polymers described in the next
chapter, vinyltrimethoxysilane is only of
limited suitability as a water scavenger.
However, the carbamate- and methacryl-
oxy-functional a-silanes are an excellent
alternative for such systems.
GENIOSIL® as Crosslinker
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Fig. 15: Synthesis of STP-U from NCO-prepolymers and aminosilanes
(catalyst)
(catalyst)
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Advantages of GENIOSIL® a-STP-E
polymers in adhesives and sealants:
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Product overview GENIOSIL ®
OrganofuncTional SILANEs
Product name Chemical name Structural formular Molecular Density Flash Boiling CAS-No
GENIOSIL® weight (25 °C) point point
Functional group [g/ml] [°C] [°C]
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Product name Chemical name Structural formular Molecular Density Flash Boiling CAS-No
GENIOSIL® weight (25 °C) point point
Functional group [g/ml] [°C] [°C]
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Product overview
Non-funcTional SILANEs
Product name Chemical name Structural formular Molecular Density Flash Boiling CAS-No
Functional group weight (25 °C) point point
[g/ml] [°C] [°C]
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ExpErtisE and sErvicE nEtwork
on FivE continEnts
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