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Fluoroalkylsilane treated
multi-color red granite is both
hydrophobic and
oleophobic.
Gelest Inc.
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Morrisville, PA 19067
Phone (215) 547-1015
Fax: (215) 547-2484
www.gelest.com
*1028_Hydrophobicity_Cvr. 2011_Layout 1 3/20/11 9:43 PM Page 2
)3 Enhance Adhesion
altered to match the
HOCH 2
CH 2
NCH 2
CH 2CH 2
Si(OEt
requirements of various
Correspondence: 11 East Steel Rd.
Increase Mechanical Properties
Propertie
dispersion of pig- N
New Coupling Agents
for Metal Substrates !
For further information consult our web site at: www.gelest.com surface properties.
ments and fillers CH 3O
Si
OCH 3
CH 3 New Coupling Agents for Vapor Phase
Deposition !
New Coupling Agents
for Proteins !
This 80-page
and immobilize catalysts and biomaterials. deposition technologies and silane chemistries
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This 48 page brochure describes chem- provided by Gelest that allow end-users to modify their
surface modification with an emphasis on istry, techniques, applications and physical
For commercial and micro-particles to achieve optimum surface properties
Gelest Inc. making surfaces hydrophobic or hydrophilic properties of silane coupling agents. for composite, separation, dispersion and other
bulk quantities contact: Stroofstrasse 27 Geb.2901 applications.
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Carbon-Carbon Bond Formation, Introduction of Aryl, Vinyl and Ethynyl Groups
Hydrophobicity, Hydrophilicity
and Silane Surface Modification
by Barry Arkles
TABLE OF CONTENTS
Silanes and Surface Modification . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2
Water, Hydrophobicity and Hydrophilicity . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 3
Wettability and Contact Angle . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 4
Critical Surface Tension and Adhesion . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 5
How does a Silane Modify a Surface? . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .6
Selecting a Silane for Surface Modification . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 7
Hydrophobic Surface Treatments . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 8
Superhydrophobicity and Oleophobicity . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 9
Hydrophilic Surface Treatments . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 10
Range of Water Interaction with Surfaces . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 11
Reacting with the Substrate . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 12
Special Topics:
Dipodal Silanes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 13
Linker Length. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 14
Embedded/Tipped Polarity . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 15
Partition, Orientation and Self-Assembly in Bonded Phases . . . . . . . . . . . . . . . . . . . 16
Modification of Metal Substrates . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 17
Difficult Substrates . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 18
Applying a Silane Surface Treatment . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 19
Biomimetic Silane Surface Treatments . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 21
Alkylphosphonic Acid Surface Treatments . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 21
Hydrophobic Silane Selection Guide. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 22
Silane Properties:
Hydrophobic Silanes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 30
Hydrophobic Silanes - Dipodal . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 60
Hydrophobic Silanes - Polymeric . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 63
Hydrophilic Silanes - Polar . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 64
Hydrophilic Silanes - Hydrogen Bonding . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 66
Hydrophilic Silanes - Hydroxylic . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 71
Hydrophilic Silanes - Ionic / Charge Inducible. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 72
Hydrophilic Silanes - Polymeric . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 74
Hydrophilic Silanes - Epoxy / Masked . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 76
Silyl Hydrides . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 77
UV Active and Fluorescent Silanes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 78
References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 80
Hydrophobicity, Hydrophilicity and Silane Surface Modification
Barry Arkles ©2011 Gelest, Inc.
OCH2CH3
CH3CH2CH2CH2CH2CH2CH2CH2— Si— OCH2CH3
OCH2CH3
organic substitution allows permanent property modification
In contrast with silanes utilized as coupling agents in adhesive applications, silanes used to
modify the surface energy or wettability of substrates under normal conditions do not impart
chemical reactivity to the substrate. They are often referred to as non-functional silanes.
The main classes of silanes utilized to effect surface energy modification without imparting
reactivity are:
3
*1028_Hydrophobicity 2011_Silane Coupling Agents-2003 2/23/11 7:49 PM Page 4
Hydrolysis Considerations
Water for hydrolysis may come from several sources.
It may be added, it may be present on the substrate surface,
or it may come from the atmosphere. The degree of polymer-
ization of the silanes is determined by the amount of water
available and the organic substituent. If the silane is added to
water and has low solubility, a high degree of polymerization is
favored. Multiple organic substitution, particularly if phenyl or
B. Arkles, CHEMTECH, 7, 766, 1977
tertiary butyl groups are involved, favors formation of stable
monomeric silanols.
Anhydrous Deposition of Silanes
The thickness of a polysiloxane layer is also determined by
the concentration of the siloxane solution. Although a monolay- R
er is generally desired, multilayer adsorption results from solu- H3C Si CH3
tions customarily used. It has been calculated that deposition OCH 3
from a 0.25% silane solution onto glass could result in three to
eight molecular layers. These multilayers could be either inter- +
connected through a loose network structure, or intermixed, OH
or both, and are, in fact, formed by most deposition techniques.
The orientation of functional groups is generally horizontal,
but not necessarily planar, on the surface of the substrate. Δ - CH3OH
The formation of covalent bonds to the surface proceeds
with a certain amount of reversibility. As water is removed, R
generally by heating to 120°C for 30 to 90 minutes or evacuation H3C Si CH3
for 2 to 6 hours, bonds may form, break, and reform to relieve
O
internal stress.
OH
H
Selecting A Silane for Surface Modification - H
O
Inorganic Substrate Perspective
O
O H
Factors influencing silane surface modification selection include: H H O
HO
OH
Concentration of surface hydroxyl groups
Type of surface hydroxyl groups
Hydrolytic Stability of the bond formed
Physical dimensions of the substrate or substrate features
1) CH3SiCl3 2)
toluene
trace H20 ethanol extraction
The methylsilicone
phase separates in
ethanol to form a
covalently attached
fibrillar network.
Automotive side windows are treated with fluoroalkylsilanes to provide Fiber diameter is
self-cleaning properties. Water beads remove soil as they are blown ~20 nm. Ellipsometry
over the glass substrate during acceleration. indicates a film thick-
SEM image ness of ~20 nm.
than 100% relative humidity. If water remains bound to a substrate under conditions of less than 100%
relative humidity, the surface is considered hygroscopic. Another description of hygroscopic water
is a boundary layer of water adsorbed on a surface less than 200nm thick that cannot be removed
without heating. A measure of the relative hygroscopic nature of surfaces is given by the water
activity, the ratio of the fugacity, or escaping tendency, of water from a surface compared to the fugacity
of pure water.
The hydrophilicity of a surface as measured or determined by contact angle is subject to inter-
ference by loosely bound oils and other contaminants. Heats of immersion and water activity
measurements are less subject to this interference. Measurements of silane-modified surfaces
demonstrate true modification of the intrinsic surface properties of substrates. If the immobilized
hydrophilic layer is in fact a thin hydrogel film, then swelling ratios at equilibrium water absorbtion
can provide useful comparative data.
The majority of surface modifications are affected by the hydrolytic E-Glass 0.10-0.12
deposition of trialkoxysilanes. Specific Wetting Surface (SWS) is a Silica, ground 1-2
value determined empirically for the amount of silane required to obtain Silica, diatomaceous 1-3.5
minimum uniform multilayer coverage on a substrate. Calcium silicate 2.6
Clay, kaolin 7
Talc 7
amount of silane (g) = amount of substrate (g) x surface area of filler (m2/g)
Silica, fumed 150-250
specific wetting surface
Specific Wetting Surface (SWS) numbers are found throughout this brochure.
Monolayer Deposition
Monolayer deposition is a widely used term, but the definition of a monolayer is usually contextual. The
simplest definition is that there is an attachment of a surface treatment molecule to every surface atom. However,
coverage of this type is probably never the case. In general, monolayer coverage refers to the reaction of the sur-
face treatment molecule with available hydroxyl groups on the surface, but this is also almost never achieved. For
example, hydrated fumed silica has 4.4-4.6 –OH/nm2. A high surface fumed silica has a surface area of 3.25 x 1020
nm2/gram and thus 1.5 x 1021 hydroxyls. If this is divided by Avogadro’s number, 6.02 x 1023, 2.4 x10-3 moles of
silane are required to provide coverage on 1 gram of fumed silica. Monolayer bonding of a silane with a molecu-
lar weight of 200 would deposit 0.5 g silane per gram of silica. In fact, most monolayer depositions of silanes
result in about 10% of the calculated requirement, i.e. 0.5g silane per gram of fumed silica.
PLEASE INQUIRE ABOUT BULK QUANTITIES
12
*1028_Hydrophobicity 2011_Silane Coupling Agents-2003 2/23/11 7:51 PM Page 13
Special Topics
Dipodal Silanes
Dipodal silanes are silanes employed in surface modifi-
cation that possess two silicon atoms capable of bonding to
surfaces through oxane bonds. Functional dipodal silanes
and combinations of non-functional dipodal silanes with
functional silanes have significant impact on substrate
bonding, hydrolytic stability and mechanical strength of Multilayer printed circuit boards use dipodal
many composites systems. They possess enabling activity silanes to maintain the integrity of the bond
in many coatings, particularly primer systems and aqueous between metal and resins by reducing
interfacial water adsorption.
immersion applications. The effect is thought to be a result
of both the increased crosslink density of the interphase and
a consequence of the fact that the resistance to hydrolysis of
dipodal materials (with the ability to form six bonds to a
substrate) is estimated at close to 100,000 times greater
than conventional coupling agents (with the ability to form
only three bonds to a substrate).
100.0
(C2H5O)3Si CH2CH2CH2CH2CH2CH2CH2CH2 Si(OC2H5)3
Water contact angle
80.0 SIB1824.0
SIB1831.0 SIB1829.0
40.0 SIB1824.0
SIO6715.0
20.0 SIB1829.0
SID4632.0 Hydrophilic Dipodal Silanes
0.0
0hr
24hr
72hr
168hr
336hr
504hr
840hr
1176hr
1680hr
2352hr
3024hr
3696hr
4368hr
5040hr
5712hr
6752hr
8064hr
8736hr
9408hr
10080hr
10752hr
11592hr
H H H
N N CH2CH2 N
CH2 CH2 CH2 CH2
CH2 CH2 CH2 CH2
Glass surfaces treated with: bridged dipodal silane SIB1824.0 1,8-bis CH2 CH2 CH2 CH2
(triethoxysilyl)octane; conventional silane SIO6715.0 n-octyltriethoxysilane; (CH3O)3Si Si(OCH 3)3 (CH3O)3Si Si(OCH 3)3
pendant dipodal silane SIB1829.0 1,2-bis(trimethoxysilyl)decane; SIB1834.0
SIB1833.0
conventional silane, SID4632.0 n-decyltriethoxysilane.
(CH3O)3SiCH2CH2CH2 O
S S O
(C2H5O)3Si NCH 2CH2OH C O(CH2CH2O)CHC
CH n
H H N 2 2 N H
C C CH2 CH2
CH2 CH2 CH2
Hydrophobic coatings applied to antennas H CH2 CH2 CH2
inhibit the formation of adsorbed water Si(OC H )
2 OH53 CH2 CH2 CH2 CH2
NCH 2CH 2
layers which become dielectric layers that (CH3O)3SiCH2CH2CH2
(C2H5O)3Si
(C2H5O)3Si Si(OC2HSi(OC
5)3
2H 5)3
Silanes with short linker length Silanes with extended linker length
OCH 3
CH3 Cl
CH3CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2 Si OCH 3
H3C Si O Si Cl SIT8572.6 OCH 3
CH3 Cl SIH5925.0
Cl
OCH 2CH3
N C CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2 Si Cl
N C CH2CH2 Si OCH 2CH3 SIC2445.0 Cl
OCH 2CH3 SIC2456.3
OC2H5 Cl
SIH6175.0 CH2CH2CH2CH2 Si Cl
HO CH2 Si OC2H5
Cl
OC2H5 SIP6724.9
O OCH 3 Cl
CH3COCH 2Si OCH 3 CH3OCH 2CH2O CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2 Si Cl
SIA0055.0
OCH 3 Cl
SIM6491.5
ties for hydrogen-bonding. The number of PEG units has rela- 41500.0
40000.0
tively small impact on contact angle of the tipped silanes 33625.0
although an increase in number of PEG units does correlate to 30000.0
decreased water contact angle. PEG units embedded in silanes
have a stronger effect on contact angle than PEG units in the 20000.0
tipped analogs. Hexadecane contact angle seems to be con- 10000.0
trolled by the number of carbon atoms in the carbon chain, 1850.0
although a step-change increase in contact angle is observed 0.0
with C18-PEG silanes. C12PEG3Si C8Si C12Si C18Si
Polarity is generally associated with hydrophilicity. Non- (SIT8163.3) (SIO6715.0) (SID4632.0)) (SIO6645.0))
polarity is generally associated with hydrophobicity. In the case Dispersion viscosity of different silane treated titanium dioxide pigment at 65%
loading in mineral oil. DodecanoylPEG3silane (SIT8186.3) with embedded
of surface treatments, it may be that the term hydrophobic polarity provides lower viscosity than octyl-, dodecyl- and octadecylsilanes.
(“water-hating” or “water fearing”) suggests a too simplistic
explanation. It appears not so much that hydrocarbons hate 65 wgt% red iron oxide in Ethylhexylpalmitate
water, but that water hates hydrocarbons. Hydrocarbons appear 600000.0
.0
.0
000
193
500
.0
200000.0
155
50
147
136
52
Embedded Polarity
10
0
100000.0
25.
Un
(S
PE IM6
SI
(S
(S
(S
C1 4632
C1 645
C8 15
(S
IO
2P 63
A0
ID
IO
tre
G6 49
2S .0
8S .0
67
Si .0)
6
EG .3
61
ate
-9 2.7
i )
0.0
C3 )
3S )
d
Si
i
15
*1028_Hydrophobicity 2011_Silane Coupling Agents-2003 2/24/11 11:19 AM Page 16
micro-contact printing and other soft lithog- SAMs of C18-Silane crystallization oxide
raphy methods. Here the silane may effect a Substrate (2-3nm)
Substrate
simple differential adsorption, or if function-
alized have a direct sensor effect.
Modification of
Metal Substrates
The optimum performance of silanes is associated
with siliceous substrates. While the use of silanes has
been extended to metal substrates, both the effective-
ness and strategies for bonding to these less-reactive
substrates vary. Four approaches of bonding to metals
have been used with differing degrees of success. In
all cases, selecting a dipodal or polymeric silane is
preferable to a conventional trialkoxy silane. Octysilane adsorbed on gold figure courtesy of
M. Banaszak-Holl
Metals that form hydrolytically stable surface
oxides, e.g. aluminum, tin, titanium. These oxidized Metals that form stable hydrides, e.g. titanium,
surfaces tend to have sufficient hydroxyl functionality zirconium, nickel. In a significant departure from tra-
to allow coupling under the same conditions applied to ditional silane coupling agent chemistry, the ability of
the siliceous substrates discussed earlier. certain metals to form so-called amorphous alloys with
hydrogen is exploited in an analogous chemistry in
Metals that form hydrolytically or mechanically which hydride functional silanes adsorb and then coor-
unstable surface oxides, e.g. iron, copper, zinc. dinate with the surface of the metal. Most silanes of
These oxidized surfaces tend to dissolve in water lead- this class possess only simple hydrocarbon substitution
ing to progressive corrosion of the substrate or form a such as octylsilane. However they do offer organic
passivating oxide layer without mechanical strength. compatibility and serve to markedly change wet-out
The successful strategies for coupling to these sub- of the substrate. Both hydride functional silanes and
strates typically involve two or more silanes. One treated metal substrates will liberate hydrogen in the
silane is a chelating agent such as a diamine, presence of base or with certain precious metals such
polyamine or polycarboxylic acid. A second silane is as platinum and associated precautions must be taken.
selected which has a reactivity with the organic com- (see p77.) H
ponent and reacts with the first silane by co-condensa- H2C CH(CH 2)8CH2Si H
tion. If a functional dipodal or polymeric silane is not SIU9048.0 H
selected, 10-20% of a non-functional dipodal silane
typically improves bond strength. Coupling Agents for Metals*
Metals that do not readily form oxides, e.g. Metal Class Screening Candidates
nickel, gold and other precious metals. Bonding to
these substrates requires coordinative bonding, typical- Copper Amine SSP-060 SIT8398.0
ly a phosphine, sulfur (mercapto), or amine functional
silane. A second silane is selected which has a reac- Gold Sulfur SIT7908.0 SIP6926.2
tivity with the organic component. If a functional Phosphorus SID4558.0 SIB1091.0
dipodal or polymeric silane is not selected, 10-20%
of a non-functional dipodal silane typically improves Iron Amine SIB1834.0 WSA-7011
bond strength. Sulfur SIB1824.6 SIM6476.0
organofunctional silanes. In some cases polymeric silanes with Hydroxylation by Water Plasma & Steam Oxidation
multiple sites for interaction with the substrate are used. Some of Various metals and metal oxides including silicon and
these, such as the polyethylenimine functional silanes can couple silicon dioxide can achieve high surface concentrations
to high sodium glasses in an aqueous environment. of hydroxyl groups after exposure to H2O/O2 in high
energy environments including steam at 1050° and
water plasma1.
1. N. Alcanter et al, in “Fundamental & Applied Aspects of Chemically
Modified Surfaces” ed. J. Blitz et al, 1999, Roy. Soc. Chem., p212.
Applying Silanes
Deposition from aqueous alcohol solutions is the most facile method for Fig. 1 Reactor for slurry
preparing silylated surfaces. A 95% ethanol-5% water solution is adjusted to treatment of powders.
pH 4.5-5.5 with acetic acid. Silane is added with stirring to yield a 2% final Separate filtration and
concentration. Five minutes should be allowed for hydrolysis and silanol for- drying steps are required.
mation. Large objects, e.g. glass plates, are dipped into the solution, agitated
gently, and removed after 1-2 minutes. They are rinsed free of excess materials by dipping briefly in
ethanol. Particles, e.g. fillers and supports, are silylated by stirring them in solution for 2-3 minutes
and then decanting the solution. The particles are usually rinsed twice briefly with ethanol. Cure of
the silane layer is for 5-10 mins at 110°C or 24 hours at room temperature (<60% relative humidity).
Deposition from aqueous solution is employed for most commercial fiberglass systems. The
alkoxysilane is dissolved at 0.5-2.0% concentration in water. For less soluble silanes, 0.1% of a non-
ionic surfactant is added prior to the silane and an emulsion rather than a solution is prepared. The
solution is adjusted to pH 5.5 with acetic acid. The solution is either sprayed onto the substrate or
employed as a dip bath. Cure is at 110-120°C for 20-30 minutes.
Stability of aqueous silane solutions varies from 2-12 hours for the simple alkyl silanes.
Poor solubility parameters limit the use of long chain alkyl and aromatic silanes by this method.
Distilled water is not necessary, but water containing fluoride ions must be avoided.
Integral blend methods are used in composite formulations. In this method the silane is
used as a simple additive. Composites can be prepared by the addition of alkoxysilanes to
dry-blends of polymer and filler prior to compounding. Generally 0.2 to 1.0 weight percent of
silane (of the total mix) is dispersed by spraying the silane in an alcohol carrier onto a pre-
blend. The addition of the silane to non-dispersed filler is not desirable in this technique since
it can lead to agglomeration. The mix is dry-blended briefly and then melt compounded.
Vacuum devolatization of byproducts of silane reaction during melt compounding is neces-
sary to achieve optimum properties. Properties are sometimes enhanced by adding 0.5-1.0%
of tetrabutyl titanate or benzyldimethylamine to the silane prior to dispersal.
Chlorosilanes can also be deposited from alcohol solution. Anhydrous alcohols, particularly
ethanol or isopropanol are preferred. The chlorosilane is added to the alcohol to yield a 2-5%
solution. The chlorosilane reacts with the alcohol producing an alkoxysilane and HCl. Progress
Fig. 3 Twin-cone blenders with
of the reaction is observed by halt of HCl evolution. Mild warming of the solution (30-40°C)
intensive mixing bars are used
promotes completion of the reaction. Part of the HCl reacts with the alcohol to produce small
quantities of alkyl halide and water. The water causes formation of silanols from alkoxysilanes. for bulk deposition of silanes
The silanols condense on the substrate. Treated substrates are cured for 5-10 mins. at 110°C or onto powders.
allowed to stand 24 hours at room temperature.
(215) 547-1015 FAX: (215) 547-2484 www.gelest.com
19
*1028_Hydrophobicity 2011_Silane Coupling Agents-2003 2/23/11 7:51 PM Page 20
Spin-On
Spin-On applications can be made under hydrolytic conditions
which favor maximum functionalization and polylayer deposition or
dry conditions which favor monolayer deposition. For hydrolytic
deposition 2-5% solutions are prepared (see deposition from aqueous
alcohol). Spin speed is low, typically 500 rpm. Following spin-depo-
sition a hold period of 3-15 minutes is required before rinse solvent. Figure 6.
Dry deposition employs solvent solutions such as methoxypropanol Spray
application
or ethyleneglycol monoacetate (EGMA). Aprotic systems utilize of silanes
toluene or THF. Silane solutions are applied at low speed under a on large
nitrogen purge. If strict monolayer deposition is preferred, the sub- structures.
strate should be heated to 50°. In some protocols, limited polylayer
formation is induced by spinning under an atmospheric ambient with
55% relative humidity.
Spray application
Formulations for spray applications vary widely depending on
end-use. They involve alcohol solutions and continuously hydrolyzed
aqueous solutions employed in architectural and masonry applica- Figure 7.
tions. The continuous hydrolysis is effected by feeding mixtures of Spray &
silane containing an acid catalyst such as acetic acid into a water contact roller
stream by means of a venturi (aspirator). Stable aqueous solutions application of
(see water-borne silanes), mixtures of silanes with limited stability silanes on
fiberglass.
(4-8 hours) and emulsions are utilized in textile and fiberglass appli-
cations. Complex mixtures with polyvinyl acetates or polyesters
enter into the latter applications as sizing formulations.
OMPH062
octadecylphosphonic acid
OMPH058
dodecylphosphonic acid
P
O O O
Methyl-Silanes. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 22
Linear Alkyl-Silanes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 24
Branched Alkyl-Silanes. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 26
Aromatic-Silanes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 28
Fluorinated Alkyl-Silanes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 30
Dialkyl-Silanes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 30
Methyl-Silanes very hydrophobic, hydrolysates stable to 425°C, acceptable performance to 600°C reported, volatile
3 Hydrolyzable Groups
Hydrolyzable Groups Product Code Product Name
chloro SIM6520.0 methyltrichlorosilane
methoxy SIM6560.0 methyltrimethoxysilane
ethoxy SIM6555.0 methyltriethoxysilane
propoxy SIM6579.0 methyltri-n-propoxysilane
methoxyalkoxy SIM6585.0 methyltris(methoxyethoxy)silane
acetoxy SIM6519.0 methyltriacetoxysilane
dimethylamine SIT8712.0 tris(dimethylamino)methylsilane
other amine SIT8710.0 tris(cyclohexylamino)methylsilane
silazane (NH)
oxime SIM6590.0 methyltris(methylethylketoximino)silane
Methyl-SiloxanylSilanes
3 or more Hydrolyzable Groups
Hydrolyzable Groups Product Code Product Name
2 silicon atom compounds
chloro SIT8572.6 trimethylsiloxytrichlorosilane
ethoxy SIT7095.0 tetraethoxy-1,3-dimethyldisiloxane
acetoxy
3 silicon atom compounds
chloro
methoxy
ethoxy
chloro
oligomeric polysiloxanes
chloro
methoxy
ethoxy
amine/silazane
silanol
selected specialties
SID4236.0 dimethyltetramethoxydisiloxane
SID3372.0 dichlorotetramethyldisiloxane
SIT7534.0 tetramethyldiethoxydisiloxane
SIP6717.0 pentamethylacetoxydisiloxane
SID3360.0 dichlorohexamethyltrisiloxane
SIB1843.0 bis(trimethylsiloxy)methylmethoxysilane
SID3394.0 1,5-diethoxyhexamethyltrisiloxane
SIB1837.0 bis(trimethylsiloxy)dichlorosilane
Space Shuttle tiles
are treated with
DMS-K05 chlorine terminated polydimethylsiloxane dimethylethoxysilane to
DMS-XM11 methoxy terminated polydimethylsiloxane reduce water absorption.
DMS-XE11 ethoxy terminated polydimethylsiloxane
DMS-N05 dimethylamine terminated polydimethylsiloxane
DMS-S12 silanol terminated polydimethylsiloxane
SID4125.0 dimethylethoxysilane
SIT8719.5 [tris(trimethylsiloxy)silylethyl]dimethylchlorosilane
24
*1028_Hydrophobicity 2011_Silane Coupling Agents-2003 2/23/11 7:52 PM Page 25
SID4591.0 dipropyltetramethyldisilazane
SIB1934.0 n-butyldimethylchlorosilane
SIH6165.6 hexylmethyldichlorosilane
SIH5845.0 heptylmethyldichlorosilane
Control
Glasscla
d ® 18
25
*1028_Hydrophobicity 2011_Silane Coupling Agents-2003 2/23/11 7:52 PM Page 26
C 12
SIA0325.0 adamantylethyltrichlorosilane
C 16
SIT8162.4 7-(trichlorosilylmethyl)pentadecane
C 18 silahydrocarbon
chloro SID4401.5 (di-n-octylmethylsilyl)ethyltrichlorosilane
C 24
chloro
C 28
chloro SIT8162.0 13-(trichlorosilylmethyl)heptacosane
SII6452.5 isobutyldimethylchlorosilane
SII6452.8 isobutylmethyldimethoxysilane
SID4065.0 (3,3-dimethylbutyl)dimethylchlorosilane
SIT7906.0 thexyldimethylchlorosilane
SIC2468.0 cyclohexylmethyldichlorosilane SIC2465.0 cyclohexyldimethylchlorosilane
SIC2469.0 cyclohexylmethyldimethoxysilane
SIB0994.0 bicycloheptyldimethylchlorosilane
SII6456.6 isooctyldimethylchlorosilane
SID4074.0 (dimethylchlorosilyl)methylpinane
SID4401.0 (di-n-octylmethylsilyl)ethyldimethylchlorosilane
SIC2266.5 11-(chlorodimethylsilylmethyl)tricosane
SIC2266.0 13-(chlorodimethylsilylmethyl)heptacosane
SIP6736.8 phenylmethylbis(dimethylamino)silane
SIP6736.3 (6-phenylhexyl)dimethylchlorosilane
SIM6511.0 (p-methylphenethyl)methyldichlorosilane
SIB1972.5 p-(t-butyl)phenethyldimethylchlorosilane
SIM6492.4 3-(p-methoxyphenyl)propylmethyldichlorosilane
SIP6723.0 m-phenoxyphenyldimethylchlorosilane
SIN6598.0 p-nonylphenoxypropyldimethylchlorosilane
DiAlkyl Silanes
2 Hydrolyzable Groups
Highest Carbon # Next Carbon # Hydrolyzable Groups Product Code Product Name
C2 C2
chloro SID3402.0 diethyldichlorosilane
ethoxy SID3404.0 diethyldiethoxysilane
C3 C3
chloro SID3537.0 diisopropyldichlorosilane
methoxy SID3538,0 diisopropyldimethoxysilane
C4 C4
chloro SID3203.0 di-n-butyldichlorosilane
methoxy SID3214.0 di-n-butyldimethoxysilane
methoxy SID3530.0 diisobutyldimethoxysilane
ethoxy SID3528.0 diisobutyldiethoxysilane
C4 C3
methoxy SII6452.6 isobutylisopropyldimethoxysilane
C5 C5
chloro SID3390.0 dicyclopentyldichlorosilane
methoxy SID3391.0 dicyclopentyldimethoxysilane
C6 C6
chloro SID3510.0 di-n-hexyldichlorosilane
chloro SID3382.0 dicyclohexyldichlorosilane
C8 C8
chloro SID4400.0 di-n-octyldichlorosilane
methoxy SID4400.4 di-n-octyldimethoxysilane
30
*1028_Hydrophobicity 2011_Silane Coupling Agents-2003 2/23/11 7:53 PM Page 31
SIN6597.4
31
*1028_Hydrophobicity 2011_Silane Coupling Agents-2003 2/23/11 7:53 PM Page 32
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2 n
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76
*1028_Hydrophobicity 2011_Silane Coupling Agents-2003 2/23/11 7:56 PM Page 77
Silyl Hydrides
Silyl Hydrides are a distinct class of silanes that behave and react very differently than conventional
silane coupling agents. Their application is limited to deposition on metals (see discussion on p. 17).
They liberate hydrogen on reaction and should be handled a with appropriate caution.
name MW bp/mm (mp) D420 nD20
.%
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MethylHydrosiloxane homopolymers are used as water-proofing agents, reducing agents and as components in some
foamed silicone systems.
polyMethylHydrosiloxanes, Trimethylsiloxy terminated Tg: -119° V.T.C: 0.50 CAS: [63148-57-2] TSCA
Molecular Mole % Equivalent Specific Refractive
COMMERCIAL
SIB1824.8
O
BIS(4-TRIETHOXYSILYLPROPYL-3-METHOXY- 777.07
10-3 M in THF
PHENYL)-1,6-HEPTANE-3,5-DIONE tech-90
O
C39H60O12Si2
UV: 220, 232(max), 354(broad)
CH3O
metal chelating chromophore
HMIS: 2-1-1-X 500mg/$180.00
(C2H5O)3SiCH2CH2CH2O
SID4352.0
NH(CH 2)3Si(OC2H5)3 3-(2,4-DINITROPHENYLAMINO)PROPYL- 387.46 (27-30°)mp 1.5665 10-5 M in THF
TRIETHOXYSILANE, 95% N-[3-(TRIETHOXYSILYL)PROPYL]-2,4-DINITROPHENYLAMINE
O2N C15H25N3O7Si viscous liquid or solid flashpoint: >110°C (230°F)
UV: 222, 258, 350(max), 410
forms χ2 non-linear optical sol-gel materials by corona poling1,2.
1. E. Toussaere et al, Non-Linear Optics, 2, 37, 1992
NO 2 2. B. Lebeau et al, J. Mater. Chem., 4, 1855, 1994
[71783-41-0] HMIS: 2-1-0-X 25g/$54.00 100g/$176.00
HO O SIH6198.0
2-HYDROXY-4-(3-METHYLDIETHOXYSILYL- 388.54
CH 3 PROPOXY)DIPHENYLKETONE, 95% viscosity, 25°: 100-125 cSt.
(C2H 5O) 2SiCH 2CH 2CH 2O
C21H28O5Si monomer for UV opaque fluids
HMIS: 2-1-1-X 25g/$86.00
SIH6200.0
2-HYDROXY-4-(3-TRIETHOXYSILYLPROPOXY)- 418.56 1.54525 10-5 M in THF
HO O
DIPHENYLKETONE, 95% viscosity, 25°: 125-150 cSt.
C22H30O6Si density: 1.12 UV: 230, 248, 296(max), 336
strong UV blocking agent for optically clear coatings, abosrbs from 210-420nm
(C2H 5O) 3SiCH 2CH 2CH 2O UV blocking agent1.
B. Anthony, US Pat. 4,495,360, 1985
[79876-59-8] TSCA HMIS: 2-1-1-X 25g/$60.00 100g/$195.00
SIM6502.0
10-4 M in THF
O-4-METHYLCOUMARINYL-N-[3-(TRIETHOXY- 423.54 (88-90°)mp
CH3
SILYL)PROPYL]CARBAMATE UV: 223, 281, 319.5(max)
O C20H29NO7Si soluble: THF
(CH3CH2O)3SiCH2CH2CH2NHCO
O O immobilizeable fluorescent compound1.
1. B. Arkles, US Pat. 4,918,200, 1990
[129119-78-4] HMIS: 2-2-1-X 10g/$120.00
OH O SIT8186.2
7-TRIETHOXYSILYLPROPOXY-5-HYDROXY- 458.58
FLAVONE UV: 350nm (max)
(C2H5O)3SiCH2CH2CH2O O C24H30O7Si
HMIS: 2-1-1-X 1.0g/$48.00 5.0g/$192.00
SIT8187.0
N-(TRIETHOXYSILYLPROPYL)DANSYLAMIDE 454.66 115-9°/0.1 1.5421 10-5 M in THF
(C2H5O)3SiCH2CH2CH2HNSO 2 5-DIMETHYLAMINO-N-(3-TRIETHOXYSILYLPROPYL)-
NAPTHALENE-1-SULFONAMIDE viscous liquid - soluble in toluene THF
C21H34N2O5SSi density: 1.12 UV: 222(max), 256, 354
fluorescent- employed as a tracer in UV cure composites
fluorescence probe for crosslinking in silicones1.
N(CH 3)2 1. P. Leezenberg et al, Chem. Mat., 7, 1784, 1995
[70880-05-6] TSCA HMIS: 2-1-1-X 0.5g/$84.00 1.0g/$148.00
CH3 SIT8188.8
N 2-(2-TRIETHOXYSILYLPROPOXY-5-METHYL- 429.59
N PHENYL)BENZOTRIAZOLE
N C22H31N3O4Si UV: 300, 330(max)
O
CH2CH2CH2Si(OCH 2CH3)3 UV blocking agent/stabilizer
HMIS: 2-1-1-X 10g/$94.00
SIT8191.0
3-(TRIETHOXYSILYLPROPYL)-p-NITRO- 370.48 (54-5°)mp
(C2H5O)3SiCH2 10-3 M in THF
BENZAMIDE
CH2 C16H26N2O6Si
O UV max: 224, 260, 292(s)
CH2
O2N C N used to prepare diazotizable supports for enzyme immobilization1.
H H. Weetall, US Pat., 3,652,761
[60871-86-5] TSCA HMIS: 2-1-1-X 25g/$60.00
SIT8192.4
10-3 M in THF
O N-TRIETHOXYSILYLPROPYL-O-QUININE- 571.79 (82-4°)mp
(C2H5O)3SiCH2CH2CH2HNCO N
URETHANE, 95% soluble: warm toluene
CH3O C30H45N3O6Si
UV max: 236(s), 274, 324, 334
N fluorescent, optically active silane
HMIS: 2-1-1-X 5.0g/$120.00
Chiral Silanes
name MW bp/mm (mp) D420 nD20
CH3
SIM6472.6
(-)-MENTHYLDIMETHYLMETHOXYSILANE 228.45
CH3
C13H28OSi
Si OCH 3
H3C
reagent for chiral separatioms
CH3
CH HMIS: 3-2-1-X 5.0g/$188.00
H3C
SIP6731.5
(R)-N-1-PHENYLETHYL-N’-TRIETHOXYSILYL- 368.55 1.0525
PROPYLUREA flashpoint: > 110°C(>230°F)
C18H32N2O4Si
optically active silane; treated surfaces resolve enantiomers
[68959-21-7] TSCA HMIS: 2-1-0-X 25g/$76.00
SIP6731.6
(S)-N-1-PHENYLETHYL-N’-TRIETHOXYSILYL- 368.55 1.0525
PROPYLUREA flashpoint: > 110°C(>230°F)
C18H32N2O4Si
optically active silane; treated surfaces resolve enantiomers
[68959-21-7] TSCA HMIS: 2-1-0-X 25g/$76.00
SIT8190.0
(S)-N-TRIETHOXYSILYLPROPYL-O-MENTHO- 406.63 0.98525 1.4526
CARBAMATE flashpoint: > 110°C(>230°F)
C20H41NO5Si optically active
[68479-61-8] TSCA HMIS: 2-1-1-X 10g/$64.00
SIT8192.4
O N-TRIETHOXYSILYLPROPYL-O-QUININE- 571.79 (82-4°)mp
(C2H5O)3SiCH2CH2CH2HNCO N URETHANE, 95% soluble: warm toluene
C30H45N3O6Si
CH3O fluorescent, optically active silane
HYDROLYTIC SENSITIVITY: 7 Si-OR reacts slowly with moisture/water
N HMIS: 2-1-1-X 5.0g/$120.00
Surface Modification with Silanes: What’s not covered in “Hydrophobicity, Hydrophilicity and
Silane Surface Modification”?
Silanes which are expected to form covalent bonds after deposition onto surfaces are discussed in
the Gelest brochure entitled “Silane Coupling Agents: Connecting Across Boundaries”
Aminosilanes which are important in some hydrophilic surface treatments are covered in detail.
Further Reading
Silane Coupling Agents - General References and Proceedings
1. B. Arkles, Tailoring Surfaces with Silanes, CHEMTECH, 7, 766-778, 1977.
2. E. Plueddemann, “Silane Coupling Agents,” Plenum, 2nd edition, 1990.
3. K. Mittal, “Silanes and Other Coupling Agents,” VSP, 1992.
4. D. Leyden and W. Collins, “Silylated Surfaces,” Gordon & Breach, 1980.
5. D. E. Leyden, “Silanes, Surfaces and Interfaces,” Gordon & Breach 1985.
6. J. Steinmetz and H. Mottola, “Chemically Modified Surfaces,” Elsevier, 1992.
7. J. Blitz and C. Little, “Fundamental & Applied Aspects of Chemically Modified Surfaces,”
Royal Society of Chemistry, 1999.
)3 Enhance Adhesion
altered to match the
HOCH 2
CH 2
NCH 2
CH 2CH 2
Si(OEt
requirements of various
Correspondence: 11 East Steel Rd.
Increase Mechanical Properties
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New Coupling Agents
for Metal Substrates !
For further information consult our web site at: www.gelest.com surface properties.
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bulk quantities contact: Stroofstrasse 27 Geb.2901 applications.
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