Open Journal of Polymer Chemistry, 2021, 11, 31-54

https ://www.sci rp.org/journal /ojpchem

ISSN Online: 2165-6711
ISSN Print: 2165-6681

Silane Terminated Prepolymers: An Alternative

to Silicones and Polyurethanes

Ravindra V. Gadhave1*, Chaitali R. Gadhave2, Pritam V. Dhawale1

Department of Polymer and Surface Engineering, Institute of Chemical Technology, Mumbai, India
1

Department of Microbiology, Savitribai Phule Pune University, Pune, India

2

How to cite this paper: Gadhave, R.V., Abstract

Gadhave, C.R. and Dhawale, P.V. (2021) Si-
lane Terminated Prepolymers: An Alterna- Silane terminated prepolymers for adhesives, sealants and coatings are of great
tive to Silicones and Polyurethanes. Open industrial importance. They are very important because of their low toxicity
Journal of Polymer Chemistry, 11, 31-54.
over polyurethanes, silicones, and solvent-based products. Hence, many pieces
https://doi.org/10.4236/ojpchem.2021.113003
of literature which deal with the synthesis, properties and applications of this
Received: August 19, 2021 Silane terminated polymers hybrid system exist. Silylated polyether (MS poly-
Accepted: August 27, 2021 mers) and Silylated Polyurethane Polymers (SPUR) are the bases for numer-
Published: August 30, 2021
ous sealants, adhesives and coatings used worldwide. A hybrid system mixed with
Copyright © 2021 by author(s) and organic-polyurethane proportion and inorganic-alkoxysilane proportion com-
Scientific Research Publishing Inc. bines the benefits of conventional polyurethane and silicone-based products.
This work is licensed under the Creative This article re views the che mistry of MS polymers and SPUR and their ad-
Commons Attribution International
vantages and disadvantages in silyl terminated prepolymer-based adhesives, sea-
License (CC BY 4.0).
http://creativecommons.org/licenses/by/4.0/ lants and coatings as we ll as provides i nformation on differe nt end applica-
Open Access tions.

Keywords
Silanes, Silane Terminated Polyethers, Silane-Terminated Polyurethanes,
Adhesives, Sealants, Coatings

1. Introduction
Hybrid Chemistry: Silane Terminated Prepolymers
Silane-terminated prepolymers have been used as resins for sealants, adhesives,
and coatings for over 30 years due to many reasons. “Silane terminated polymers-
Hybrid” is of increasing interest because they can be formulated to provide the
best properties of two or more families of polymeric materials while limiting their
individual inherent weaknesses. The silyl terminated adhesives, sealants and coat-
ings systems are also isocyanate-free systems. They also provide better adhesion,

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R. V. Gadha ve et al.

abrasion resistance, better stability and low-temperature e xtrudability than sili-

cone and polyurethane sealants [1] [2].
Silane terminated prepolymers can be formulated into one-component, two-
compone nt, and isoc yanate-free products, where, due to their low viscosity,
solve nts can be exc luded. It is be neficial that the products c ure without bubble
formation e ven under unfavorable weather conditions. Nowadays, many wood
flooring adhesi ves are based on silane termi nated polymers, as are several as-
sembly adhesives and exterior waterproofing systems. In these kinds of applica-
tions, the elasticity of the cured materials and their wide adhesion profile are of
particular importance. Applications in which bonded joints or waterproofing
membranes are e xposed to high dynamic loads remain the domain of polyure-
thane chemistry. Recently, adhesives used i n the automotive or white goods in-
dustry are, for example, Silane terminated polymers based, including waterproofing
membranes for roofs, balconies, and patios. After curing, all these industrial adhe-
sives, sealants and coatings are highly elastic and have high tear and tensile strength
[3].
This article reviews the advantages and disadvantages of silyl termi nated pre-
polymer-based adhesives, sealants and coatings and provides information on dif-
ferent end applications. Both silylated polyether (MS polymers) and Silylated Po-
lyurethane Polymers (SPUR) are discussed here.

2. An Overview of Silanes
2.1. Chemistry
Silicon (Si) belongs to the main Group 14 (formerly IVA) with carbon (C), ger-
manium ( Ge), tin (Sn), and lead ( Pb) on the periodic table and it has four va-
lence electrons. The difference between the two groups is a partial filling e lectron
configuration of 3d - 5d orbitals in Group 14 [4]. The empty 3d orbital of Si makes
it chemically different from other Group 14 elements, in terms of structure, reactiv-
ity and thereby physical and chemical properties [5] [6]. Carbon (6C) is a typical
non-metal and silicon (14Si) is a metalloid, semi-metal (a semi-conductor). Silicon
is found as silica and numerous silicates, aluminous silicates in earth. Carbon
can form endlessly long chains with other carbon atoms -(-C-C-)n-. Si licon can
also bond to other silicon atoms (-Si-Si-)n- but with far shorter chain length (only
up to 2 - 3 units) and such compounds are, in contrary, unstable. This is owing
to the C-C bond energy ( 356 kJ/mol) which is much higher than the Si-Si bond
energy (226 kJ/mol). However, Silicon can form indefinitely long chains, but with
oxygen atoms to form a siloxane linkage (-O-Si-O-)n because of a very strong Si-O
bond energy (286 KJ/mol). Silicon compounds are more reactive than carbon com-
pounds because of the presence of vacant 3d orbital.
Organosilicon compounds are widely found in adhesives, coatings, caulks, and
sealers. Other remarkable uses include both plant and agricultural control chemi-
cals (fungicides and herbicides). The term silane, once limited to silicon hydrides,
has grown to include functional silanes, where one or more hydrogen atoms are
replaced by a radical such as Cl, F, CH3, etc. Si lanes find e xtensive use as pre-

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 R. V. Gadha ve et al.

cursors in the chemical industry, as reagent in the production of high purity sil-
icon, as surface modifiers for adhesion of various coating, as the transition com-
pound from organic to inorganic materials, as precursors in producing a range
of products, including si licones, and many other uses [5].
Organo si lanes are synthesized from SiO2, silica one of the most abundant
materials in the earth through a series of reaction. Silica is reduced to silicon which
reacts with hydrogen chloride to yield trichlorosilane, HSiCl3. Then, trichlorosilane
reacts with alkene and finally followed by alcoholysis, i.e., reaction with alcohol,
to form the functional silanes. A silane coupling agent, which is a trialkoxysilane,
contains two functional groups at the ends of its molecular backbone, and which
connect an unpolymerized resin matrix and an inorganic substrate (surface). A gen-
eral formula or such bifunctional silane is L-(CH2)k-Si-(OR)3, where L is an orga-
nofunctional group (e.g., methacrylate, acrylate, isocyanato, epoxy), and these grou-
ps provide the organic compatibility which allows the silane to form interpene-
trating networks, or in the case of reactive organofunctional silanes, to co-react with
the coating polymer and (CH2) is a linker (spacer) group that k separates the or-
ganofunctional group and the Si atom. OR is a hydrolysable alkoxyl group (me-
thoxy, ethoxy).
At ambient temperature, silane is activated by acid (acetic acid) to form sila-
nol (SiOH) before they can bond to the inorganic substrate. The general formula
of an alkoxy silane shows two classes of moieties attached to the silicon atom:
Alkyl and aryl silanes are utilized to improve gloss, hiding power, mixing time,
and other properties related to improved pigme nt dispersion. Alkyl and aryl si-
lanes are also utilized to provide hydrophobic surfaces in applications such as wa-
ter repellents. The X represents alkoxy moieties, most typically methoxy or etho-
xy, which react with the various forms of hydroxyl groups and liberate metha-
nol or ethanol. These groups (Table 1) can provide the linkage with i norganic
substrates, pigment, or filler to improve coating integrity and adhesion. The me-
thoxy groups are also capable of reacting with hydroxy functional polymers [5]
[6].

2.2. Activation and Hydrolysis of Silane

Organofunctional silanes contain two different reactive functional groups that
can react and couple with various inorganic and organic materials. Thus, they act
as adhesion promoters to join dissimilar materials. These functional silane coupl-
ing age nts are first activated by hydrolysis (=SiOR=SiOH) before they can bond,
via hydroxyl groups on the substrate surface.
The first step of hydrolysis of silane to silanol (=SiOH) takes place by the fast
and reversible protonation of the alkoxy group of the silane at pH 4 ash shown
in Figure 1. Then, it undergoes a bimolecular nucleophilic substitution (SN2) reac-
tion at the central silicon atom. This first involves the backside attack by a water
molecule (nuc leophile) to the central silicon atom (electrophile), to give a pen-
ta-coordinate trigonal bipyramidal transition state. A new bond is then formed
between the nuc leophile and the silicon center, and a bond is cleaved between

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R. V. Gadha ve et al.

Table 1. Classification and uses of silanes [7].

Inorganic silanes
● Precursor to production of organ silanes
● Precursor to production of electronic and solar grade silicons
● Reducing agent
● Used to produce Integrated Circuit (IC) devices and electrical isolation for IC interconnects
Amino silanes
● Promotes adhesion to various substrates, serves as coupling agent, and is used as resin additives
● Used with sulphur and peroxide cured rubber, polyester, Polyolefins, styrenics and acrylics
● Used with ethylene to copolymerize for moisture induced coupling of polyethylene
● Used with polyethylene for moisture induced coupling
● Surface modifier for mineral fillers as plastics

Epoxy silanes
● Adhesion promoter
● Surface treatment for fillers and reinforcement fillers

Methacryl silanes
● Used for free-radical, crosslinked polyester, rubber, poly(olefins), styrenics, and acrylics
● Promotes adhesion and serves as coupling agent including moisture crosslinking of acrylics
● Coupling agent between fillers and fiberglass to resins

Alkyl silanes
• Silicone synthesis
• Hydrophobic surface treatment

Phenyl silanes
● Improves thermal stability of both surfaces and silane coupling agents
● Hydrophobic treatment of both surfaces and silane coupling agents
● Use in synthesis of silanes and siloxanes

Organ chlorosilanes
● Protecting agents for intermediates in pharmaceutical synthesis (methyl chlorosilanes)
● Use in synthesis of silanes and siloxanes

Figure 1. Silane hydrolysis mechanism in an acidic medium (OR is an alkoxy group an d Y is an organofunctional group).

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 R. V. Gadha ve et al.

the leaving group (alcohol) and the silicon center. Finally, this gives the product
with inversion of confi guration after the hydrolysis process [6] [ 7] [8].

2.3. Factors Affecting Silane Hydrolysis

The rate of silane hydrolysis depends among others on the silane molecular struc-
ture, its concentration, pH, temperature, humidity, and solvent system. Ethanol is
usually a part of the solvent system as si lanes dissolve easily i n ethanol but not in
water. The bulkiness of alkoxy groups would affect the rate of hydrolysis. For si-
lane coupling agents with bulky alkoxy groups, the steric repulsion of water mov-
ing towards to the silicon atom is increased as shown in Figure 2.
This said, the hydrolysis rate decreases with the large size of alkoxy groups:
pentoxy < butoxy < propoxy < ethoxy < methoxy. The silane hydrolysis is strongly
pH dependent. The silane hydrolysis rate is fast at acidic and alkaline medium, but
it reaches a minimum at neutral pH for alkoxysilanes. Temperature is an impor-
tant parameter: the hydrolysis reaction rate increases with temperature that fol-
lows the Arrhenius law. The hydrolysis rate is dependent on the nature of co-solvent
in the solvent mixture. The hydrolysis rate depends on the hydrophilicity of the
solvent. As the hydrophilicity decreases from methanol, ethanol, and propan-1-ol,
the hydrolysis rate decreases [5] [9].
The silanes employed in improving adhesion and surface modification were
usually alkoxysilanes. Before or during application and bonding processes alkox-
ysilanes were hydrolysed, initiating a complex cascade of reactions. In vast ma-
jority of silane surface treatment applications, the alkoxy groups of trialkoxy si-
lanes were hydrolysed to form silane-containing species. The silanol-containing spe-
cies were highly reactive intermediates which were responsible for bond forma-
tion with the substrate. Hydrolysis of trialkoxy groups may occ ur during for-
mal preparation of aqueous solution or the reaction of the silane with adsorbed
moisture on substrate surfaces. In principle, if si lanol materials were stable,
they would be prefe rred for surface treatments. Most silanes employe d in sur-
face treatments do not form stable monomeric silanols. Silanols usually condense

Figure 2. The steric effect of alkoxy groups on silane hydrolysis of tripropoxyvinylsilane and
Trimethoxyvinylsilane.

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R. V. Gadha ve et al.

with themselves or with alkoxysilanes to form siloxanes. Trialkoxysilanes are

stable sources for silanols, but they have low intrinsic viscosity, low solubility in
aqueous solutions and by-products of hydrolysis which may be undesirable from
a flammability and toxic perspective. Alkoxysilanes undergo hydrolysis by both
base- and acid-catalysed mechanisms. In contact with high-purity (18 × 106 Ω·cm)
water under neutral, low-ionic conditions in non-glass containers, alkoxysilanes
bearing chlorosilanes and acetoxysilanes, the products of alkoxysilanes hydroly-
sis don’t propagate the hydrolysis reaction. In contact with tap water hydrolysis
of alkoxysilanes was substantial, if not complete within hours. The same factors
which accelerate the hydrolysis of alkoxysilanes also accelerate the condensation
of silanols with other si lanols and their alkoxy precursor’s [10].

2.4. Classification of Silanes

2.4.1. Functional Silanes
Organofunctional silanes contain two different reactive functional groups that
can react and couple with various inorganic and organic materials. Thus, they act
as adhesion promoters to increase the union of dissimilar materials. The hydro-
lysable functional groups react to the surface hydroxyl groups of i norganic sub-
strates. The organic functional groups react with functional groups of resins (Table
2). Wide selections of the organofunctional groups of the silanes can react with
different functional groups of dental resin composites. For example, epoxy resins
with amino or epoxy silanes, vinyl or acrylate resins with vinyl or methacrylate
silanes, etc.
α-silane s and γ-silane s
The re lative ly slow crossli nking kinetics of the standard si lane termi nated
polymers are due to the molecular structure of the terminal silyl group. With

Table 2. Performance comparison of Silane terminated prepolymers, Polyurethane, and

Silicone Sealants [43].

Silane terminated
Property Polyurethane Silicone
prepolymers

Environmental friendliness 10 5 9
Non-bubbling 10 6 10
Low temperature gunnability 10 8 10
Stain resistance 8 8 5
Weather resistance 8 6 10
Adhesion to various substrates 10 5 8
Mechanical properties 10 10 10
Heat resistance, mechanical stability 9 8 10
Non-dirt pickup 10 10 5
Storage stability 10 7 9
Paintability with water-based paint 10 10 3

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 R. V. Gadha ve et al.

γ-alkoxysilanes, the moisture induced crosslinking reaction takes place consi-

derably more slowly than with the highly reactive α-alkoxysilanes. In α-silanes,
the electron donor is attached to the silicon atom via a methylene group. With
this configuration, the alkoxy groups are activated, so that the crosslinking reac-
tion is accelerated considerably. This is the difference between α and γ -silanes as
shown in Figure 3, α- and γ -alkoxysilanes in organofunctional alkoxysilanes, at
least one of the four groups bound to the silicon atom is an alkoxy group (–OR).
Depending on the number of alkoxy groups, a distinction is made between bi-
functional (two alkoxy group) and trifunctional silanes (three alkoxy group).
The alkoxy groups are able to hydrolyze. The reaction with water leads to the
formation of a siloxane network. In addition to the alkoxy groups, there is a func-
tional organic group on the silicon atom (X). Via X, a silane can also bind to an
organic molecule. This is how Silane-terminated prepolymers are produced. An
important structural feature of organofunctional alkoxysi lanes is the length of
the hydrocarbon chai n in the reactive organic group.
The γ -silanes used industrially so far contain a propyle ne group in their re-
active organic group (–CH2–CH2–CH2–) as spacer between the silicon atom and
the organofunctional group, so that X is in the γ -position (relative to the Si atom).
In α-silanes, the considerably shorter methylene group (–CH2–) is located be-
tween the silicon atom and X. In this case, X is α-terminal. The length of the hy-
drocarbon chain has a major influence on how firmly the alkoxy groups are bound
to the silicon atom, and thus on the speed of crosslinking in the presence of mois-
ture.
The α-effect, in α-alkoxysilanes, the reason for this effect is an electronic inte-
raction between the silicon atom and the electron donor in the α-position. As a
result of back-bonding, the electron density is shifted from the donor to the sili-
con atom, and the Si-O bonds are weakened. The alkoxy groups split off more
easily and hydrolysis is accelerated [11].

2.4.2. Non-Functional Silanes

Non-functional silanes contain only reactive alkoxy (-OR) functional groups that
after hydrolysis to silanol groups react with surface hydroxyl groups of i norganic
substrates. A bis-functional silane has two silicon atoms, each containing three
hydrolysable alkoxy groups and they are also called cross-linking or dipodal si-
lane. The purpose of this cross-linking silane is to connect the silane molecules

Figure 3. α- and γ-alkoxysilanes in organofunctional alkoxysilanes.

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R. V. Gadha ve et al.

more extensively by forming three-dimensional siloxane networks and inter-

connecting with the functional silanes. Thus, a rigid siloxane network is formed
and as a result, more energy is required to break apart the cross-linking network.
Furthermore, the penetration of water molecules into the inner interfacial layer
becomes more and more difficult as the degree of the cross-linking siloxane net-
work increases [5] [6].

3. Silane Coupling Agents

Silane coupli ng age nts can form a durable bond between organic and i norganic
materials. Interfaces involving such materials have become a dynamic area of che-
mistry in which surfaces have been modified to generate desired heterogeneous
environments or to incorporate the bulk properties of different phases into a uni-
form composite structure [8]. Coupling agent formula is shown in Figure 4. Coupl-
ing age nts bind organic polymers to fillers such as fiberglass/silica or mineral fil-
lers like talc, mica, clay, and wollastonite. Silane as a coupling agent, silanes he lp
to improve bonding and mixing as we ll as to increase the matrix stre ngth be-
tween these polymers and fillers [ 6].
The general formula for a silane coupling agent typically shows the two c lasses
of functionality. X is a hydrolysable group typically alkoxy, acyloxy, halogen or
amine. The R group is a nonhydrolyzable organic radical that may possess a func-
tionality that imparts desired characteristics.

4. Silane Terminated Polyurethane

In 2004 O’Connor et al. [12] were the first to review the synthesis methods and
development of silyl-terminated polyurethanes for construction applications. The
use of organofunctional silanes as crosslinking units for polyurethanes was first
reported in the early 1970s by a patent by 3 M [13]. Brode and Conte [14] followed
shortly and synthesized SPUR prepolymer with different aliphatic and mercapto
silanes. In the early 1980’s Berger et al. [15] improved this new technology by
using secondary amino bis-silanes which significantly improved the properties of
the adhesives, sealants, and coatings with respect to flexibility and curing times.
In the first step a conventional polyurethane prepolymer is formed by reaction
of a polyol with an excess amount of a diisocyanate. The free isocyanate groups
are then end-capped with compounds containing reactive alkoxysilane groups.
After application the alkoxysilane end groups undergo hydrolysis and condensa-
tion reactions in the presence of moisture giving the cured prepolymers desired.

Figure 4. Formula for a silane coupling agent.

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 R. V. Gadha ve et al.

In 2006, Xu et al. [16] reported the synthesis and shape memory effects of
Si-O-Si cross-linked hybrid polyurethanes. The first step is the synthesis of a si-
lane end-capper by Michael addition of aminosilane and acrylate. In the second
step a diisocyanate and polyol compound are reacted to give the polyurethane
backbone having free isocyanate groups. In the third step the isocyanate-terminated
polyurethane reacts with the silane end-capper and results in the inorganic-organic
hybrid material. The same synthesis strategy was applied by Nomura et al. in
2007 [17] and is shown in Figure 5.
Subramani et al. [18] [19] [20] used a slightly different route to prepare the
SPUR desired. A polyol is reacted with a dimethylol propionic acid (DMPA) and
a diisocyanate in the first step. The free isocyanate groups of the polyurethane
are then end-capped with an amino alkoxysilane. Furthermore, acetone is added
in order to reduce the viscosity of the polymer and triethylamine to neutralize
the COOH groups. Sardon et al. [21] used the same reaction pathway by using
acetone as solvent of the reaction. After functionalization of the polyurethane with
an aminoalkoxysilane the emulsification process is started by the addition of wa-
ter, and acetone is removed by distillation. The reaction scheme of this synthetic
route is shown i n Fig ure 6.

Figure 5. Synthesis pathway for SPUR’s.

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R. V. Gadha ve et al.

Triethoxysilane and linseed polyol as inorganic and organic precursors were

used by Akram et al. [22]. This so-called Si/li nseed polyol is further treated with
a diisocyanate to give organic-inorganic hybrid polyurethane composites. Ve-
ga-Baudrit et al. [ 23] investigated the properties of thermoplastic polyurethanes
by agglomeration of nano silica particles within a polyurethane matrix. The ther-
moplastic polyurethane is prepared by the standard prepolymer method and mixed
with the nano silica in 2-butanone.

4.1. Steps of Silane Terminated Polyurethane Synthesis

4.1.1. Polyurethane Formation
The network formation process of diol-diisocyanate systems catalyzed by dibu-
tyltin dilaurate was investigated by Dusek et al. [24] in 1990. The most impor-
tant reactions that occur are summarized in Fig ure 7. They claim that the molar

Figure 6. Synthesis of STPUs [21].

Figure 7. Isocyanate side reactions.

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 R. V. Gadha ve et al.

ratio OH/NCO has an impact on the importance of the side reactions. Side reac-
tions cannot be inhibited if isocyanate is in excess. However, at lower tempera-
tures (≤60˚C) the formation of biuret and allophanate is very slow.

4.1.2. End-Capping
The end-capping reaction is done with di- or tri-functional ami no silanes [ 25]
[26]. The ami no groups are reacted with the free isocyanates to give stable urea
groups. A tri-functional silane having three methoxy or ethoxy groups induces high-
er cross linking and faster cure. Methoxy si lanes as end-cappers also lead to fast-
er cure rates than those of ethoxy silanes [27].
Isocyanate functional silanes couple with the polyol. Alkanolamine functional
silanes react with the isocyanate to form urethane linkages, while amine si lanes
react with the isocyanates to yield urea linkages as shown in Fig ure 8 [28].

Figure 8. Polyurethane coupling reaction.

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R. V. Gadha ve et al.

Secondary amino silanes have the general ability to convert isocyanate func-
tional urethane prepolymers to systems that crosslink in the presence of water
and a tin catalyst as shown i n Figure 9. The preferred amino si lanes are second-
ary containing methyl, ethyl or butyl substitutions on nitrogen.
From an industrial viewpoint, much attention has been paid to one-component,
solvent-free urethane elastic adhesives based on the isocyanate-terminated po-
lyurethanes. However, these Isocyanate-terminated polyurethanes have several
drawbacks, such as a slow curing speed, a low bonding strength due to foaming
by carbon dioxide ge nerated by the reaction of isocyanate groups with water,
and toxicity of the isocyanate groups. These inadequacies motivated led to develop
alkoxy si lyl compounds with amino groups, which can be used as end-capping
silane age nts to modify the isocyanate groups of polyurethanes as shown i n Fig-
ure 10.

Figure 9. Moisture curable silylated polyurethane.

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 R. V. Gadha ve et al.

Figure 10. Reaction of isocyanate terminated Polyurethane prepolymer with primary amino silane and an active hy-
drogen compoun d.

Michael addition is known as a process in which an amino group reacts quan-

titatively with an α, β-unsaturated carbonyl group under mild conditions. The
Michael addition technology was applied to synthesize novel silane end cappers
by the reaction of a commercial primary amino silane (3-amino propyl trimethoxy
silane) and a variety of acrylates. The resulting trialkoxysilane compound having
mainly secondary ami ne groups could be successfully use d as an end-capping
agent for the termi nal isoc yanate groups of conve ntional polyure thanes. The
physical properties, the curing speed, the te nsile shear bond strength, and the
adherence were found to be controlled by the structures of the silane end cappers,
the main chain of the polyurethane, and the composition of the silane end cap-

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R. V. Gadha ve et al.

per and the isocyanate-terminated polyurethane in the feed [29] [30] [31] [ 32]
[33].
As the silane-end capping agents are costly. Wang and their team members
[34], two silane-terminated Polyurethane prepolymer were synthesized by end
capping with γ -amino propyl trimethoxy silane (APTMS). First Silylated prepo-
lymer was partially end capped with APTMS, while free NCO groups are free and
Second Si lylated prepolymer was end capped partially with APTMS and partially
with active hydrogen compounds which has an inert group attached to it such as
Methanol. Both pre-polymers were formulated with same formulations and second
silyated polyurethane pre-polymer shows better mechanical properties [34] [35].
Silylated polyurethane obtainable by Ralf Baetzge n and their team members
comprising the following steps as shown in Fig ure 11 [36].
The silylated Polyurethane are suitable for use i n a preparation as an adhesive,
sealants, or a coating agent. Modified-silane adhesives and sealants have a po-
lyether backbone and the reactive terminal and Crosslinkable termi nal groups
are alkoxy groups. These hybrid Polyurethanes have the advantages of being free
from terminal isocyanates groups [ 37] [ 38] [39].

Figure 11. Synthesis of SPUR using isocyanate silanes.

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 R. V. Gadha ve et al.

5. Silane Terminated Polyethers

All commercially available silane modified polymers contain alkoxy silyl groups
and are thus able to crosslink in the presence of moisture [40]. They differ in their
organic structure, notably the manner the silyl groups are linked to the polymer
backbone and the distance between the silyl groups and the backbone. In the case
of silane-terminated polyethers, the silyl groups are coupled to the ends of the
polyether backbone via an alkylene unit and a urethane group. The alkylene unit
can either be a methylene group, in which case it is a silane terminated polyeth-
er, or a propyle ne group, in which case it is a silane terminated polyether. The
length of the alkyle ne unit in-flue nces the reactivity of the alkoxysilylations of
silane-terminated polyethers cure rapidly without needing a tin catalyst; the pres-
ence of a catalytic primary amino compound will suffice to kick off the catalytic
reaction.

5.1. Silane Terminated Prepolymers-Chemistry

α-silane-terminated polyether is used as resin, the fully cured adhesive offers a
combination of strength and elasticity that is ideal for various applications. The
α-effect makes the innovative resin highly reactive. The setting speed can be ad-
justed by the choice of catalyst system, and even tin-free catalyst systems are poss-
ible. The high reactivity characteristic of α-silanes is retained even whe n the y are
attached to organic polymers. α-silane terminated polymers always crosslink very
quickly. Figure 12 and Figure 13 illustrates α and γ silane terminated prepoly-
mers.
Even dimethoxysilyl and triethoxysilyl end groups are more reactive in α-silane-
terminated polyethers than the trimethoxysilyl end groups of γ -silane-terminated
polyethers. Difunctional silanes have the advantage that they release less metha-
nol during the crosslinking process. In addition, a lower crosslinking de nsity is
obtained with them than with trifunctional silanes, thus favoring the formation
of a more elastic vulcanizate. Alkoxysilanes with an α-terminal isocyanate group
have proven particularly useful in reacting with organic polymers as shown in Fig-
ure 12. There are three reasons for this: first, the isocyanate group (–N=C=O)
permits bonding to various organic base polymers. Second, the bonding reaction
is easy to control, and third, the reaction is quantitative. In the resulting α-silane-
terminated polymer, the terminal silyl groups are irreversibly joined to the poly-
mer chain via a stable urethane bond; the product contains no free isocyanate
groups [41].

5.2. Fast Curing Technology

Chemical modification of the silane functional group is another tool to improve
the properties of the silane-terminated polyether’s. The current market trend
requires adhesives with very fast strength development and faster curing. Draw-
back of these systems is however that most of these adhesive’s lack in elongation
or elasticity. The first generation of MS Polymer with the dimethoxy-methyl silyl

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R. V. Gadha ve et al.

Figure 12. Synthesis of α silane terminated prepolymers.

end groups has an exce llent e lastic behavior but is relatively low in reactivity.
Faster curing systems were later deve loped by replacing the dimethoxymethyl
silyl group with trimethoxysilyl groups, as consequence that elongation dropped,

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 R. V. Gadha ve et al.

Figure 13. α and γ silane terminated prepolymers.

certainly with the si lylated-ed polyurethane types. The next step was the devel-
opment of very fast curing systems, such as the α-type MS polymer, which keeps
the inherent low elongation, resulti ng in more brittle products.

5.3. High Strength Technology

The second-generation MS Polymer modified with polyacrylate can control the
morphology. By redesigni ng of the backbone and polymer structure, glass tran-
sition temperature (Tg) of the polymer can be controlled and consequently the
compatibility of the polymers before and after curing can be manipulated. Acrylic
domains are formed in a polyether matrix and these acrylic domains e nhance the
strength significantly. Moreover, the acrylic domains will provide an improved ad-
hesion to plastic substrates.

6. Curing Mechanism: MS & SPUR Adhesives, Sealants, and

Coatings
The silane groups provide a non-isocyanate curing mechanism, better adhesion
to various substrates, and excellent storage stability. These reactive end-groups
cures in the presence of moisture in the atmosphere and an appropriate catalyst
by means of an alkoxy reaction that is different than the conventional silicone cure
mechanism. The water reacts with the silane group to produce si lanol. Further
reaction of the silanol with either another silanol or methoxysilane produces three-

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R. V. Gadha ve et al.

dimensional siloxane linkages. The crosslinking reaction proceeds in two steps

illustrated in the Figure 14 and Figure 15 below.
Step 1:

Figure 14. Conversion from methoxysilane to silanol.

Step 2:

Figure 15. Condensation of silanol groups to form siloxane crosslink.

To make the curing mechanism happe n, both water (e.g., ambient moisture)
and a catalyst are required.

7. Key Properties and Performance of MS and SPUR

1) Heal th and Safety during Formul ation and Application: Perhaps the
most compelling value proposition associated with MS Polymer adhesives, sea-
lants and coatings are their lack of free isocyanates and solvents. Their absence
broadens the range of formulation possibilities and allows the end product to
meet stringent e nvironmental regulations.
2) Lack of I soc yanates: The silyl-terminated polymer eliminates the need for
isocyanate. Isocyanates are highly reactive chemicals. Consequently, formula-
tions containing isocyanates must be protected from contact with reactive
agents, includi ng moisture, as this will drastically decrease shelf life. Isocyanates
are also considered to be hazardous materials to use. Since no isocyanates are
present, bubbling during curi ng is not a concern as it often is with polyurethane
systems. Bubbles can damage the integrity of the sealant or adhesive. MS Poly-
mer sealants do no bubble on the surface at all. The sealants and coatings surface
is kept smooth and intact.
3) Lack of Solvents: The low viscosity of Silane terminated prepolymers al-
lows for a solvent-free formulation that is less dependent on temperature change.
Therefore, formulations are easy to process and have low temperature gunnabil-
ity. The absence of solvent provides environmentally friendly sealants that meet
environmental regulations regarding volatile organic contents (VOCs), out-gassing,
and toxicity. Furthermore, the lack of solvents protects the formulator from the
rising cost of solve nt raw materials and VOC mitigating facilities.
4) Applications: One-part Silane terminated prepolymers based adhesives,

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 R. V. Gadha ve et al.

sealants and coatings cure relative ly fast eve n at low temperatures. Thus, they
find use in applications where property development speed is important Once
cured, Silane terminated prepolymers based adhesives, sealants and coatings also
exhibit little dirt pick up when compared to silicone-based systems.
5) Pe rformance during Service : The rise in Silane terminated prepolymers
based adhesives, sealants and coatings popularity has been primarily due to its
versatility and well-balanced properties [42].
Compared with the other two types of sealants, Si lane terminated prepolymers
based adhesives, sealants and coatings have we ll balanced properties and per-
formance. Some of the unique properties of Silane termi nated prepolymers are:
● Environmental friendli ness (solvent free and -NCO free)
● Low temperature gunnability and flowability
● Silane terminated prepolymers based sealants do not stain as some silicone
sealants do because of low molecular weight silicon materials that bleed from
the surface of sealed joints.
● Silane terminated prepolymers adhesives, sealants and coatings provide good
paintability unlike silicone sealants.
● Silane terminated prepolymers shows no cracking, splitti ng, discoloration or
adhesion failure after seve n years of testi ng in desert climate.
● Silane terminated prepolymers based adhesives, sealants and coatings pro-
vide adhesion to various substrates including metals, plastics, wood, and ce-
ramics.
● Shelf life is excellent although must be protected from moisture.
Performance Comparison of Silane terminated prepolymers, Polyurethane, and
Silicone based Sealants is shown in Table 2.

8. Applications of Silane Terminated Prepolymers

Adhesives, sealants and coatings, as the y are used in many fields, require a series
of different properties for unique function. Costumers are looking for high-per-
formance construction adhesives and sealants useful for a various type of appli-
cations. In modern construction, water-based and solve nt-free systems are do-
minating due to their low toxicity with regard to the environment [44] [45]. These
types of adhesives and sealants avoid strong curing shrinkage, which typically
appears in solvent-based systems, and, additionally, the liberation of volatile com-
pounds is reduced. Polyurethanes have grown commercially as adhesives, sealants
and coatings as the y have excelle nt adhesion to a wide range of materials, perfect
abrasion resistance, good flexibility and hardness. These properties make them
useful for products such as coatings, adhesives and sealants. So-called Silyl-Termi-
nated Polyurethanes (STPU) combine the advantages of polyurethane and sili-
cone sealants [46].
That’s why such cases call for low-modulus e lastic hybrid sealants that require
only a little force to stretch or compress. When the strain is removed, they largely
return to their original form. These types of sealants absorb the components’ move-

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R. V. Gadha ve et al.

ments and thus lessen the strain on the joint edges. In practice, a sealant may al-
so be required to bond the two substrates together. Experts refer to this as an
adhesive sealant or elastic adhesive. While such an allrounder should be capable
of transferring forces, it should also be e lastic, so that it can accommodate the
component’s movement. This is the case for assembly adhesives, for example,
which should be strong yet elastic [47]. There are many applications in which
the bonded joint must be not only strong but also elastic. Elasticity becomes more
important as soon as the bonded joint is subjected to a dynamic load. Since elas-
tic adhesives deform reversibly and can absorb dynamic loads in the process,
they have become firmly established in many applications. It would be unthink-
able today to assemble the bodywork of buses, railroad cars, campers, mobile homes
and refrigerated trucks, for example, without elastic adhesives. Elastic adhesives
are also becoming increasingly common in aircraft construction and shipbuild-
ing. The binders used in elastic adhesives derive mainly from two polymer classes,
namely polyurethanes (PUR) and silane terminated polymers. Polyurethanes cros-
slink using isocyanate chemistry. Silane-terminated prepolymers crosslink via
the alkoxysi lane units attached to the ends of the polymer chain. These polymers
form highly stable silicon-oxygen-silicon bonds when they cure, which is typical
of silicones. Aside from unde niable advantages, all the commercially available
binders suitable for formulating elastic adhesives also have some specific disad-
vantages. Polyurethane systems, for example, cure to produce materials with very
high tensile strengths. However, in terms of their elongation at break and adhe-
sion to various substrates (without pretreatment), they are inferior to the vulca-
nizates of adhesives formulate d with si lane-te rminated polyethe rs. Si lane-ter-
minated polyurethane s, which could be described as a combination of the two
systems, are either not very easy to compound because of their high viscosity
[48].

9. Futuristic Developments
The advantages arising from ne w molecular design for the silylated polymer
were improved elastic recovery and better through cure, eve n in deep layers or
for bonding of large surface areas. Moreover, improved adhesion to a very wide
variety of substrates was achieved by adaptation of the polymer backbone, for
example by adjusti ng its polarity and crystallinity. These properties allowed the
use of polymers in applications that were pre viously addressed only with diffi-
culty [49].

10. Conclusion
Combining different polymer chemistries to develop new products can be chal-
lenging, but the potential benefits of success are making this a hot topic in the
adhesives, sealants and coatings industries. Silylated prepolymers are considered
to be “hybrid” molecules because they provide the best properties of polyurethane
and silicone whi le limiting their inherent weaknesses. In addition to their unique

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 R. V. Gadha ve et al.

performance and application properties, these polymers have achieved wide-

spread acceptance due to their solvent-free and isocyanate-free nature. Here, we
discussed the chemistry, advantages and disadvantages of Silylated prepolymers-
based adhesives, sealants and coatings and provides information on different end
applications. In order to cope with the current and future market requirements,
the new generation of silane-terminated polymer technologies has greater impor-
tance in terms of final applications like low viscous reactive diluents, non-ye-
llowing polyacrylate modified high strength polymers and fast curing elastic po-
lymers. Comparisons to conventional silicones, polyurethanes and acrylic dem-
onstrate that Silylated prepolymers-based products offer excellent properties for
applications requiring long-term exposure to chemicals. Since its introduction,
additional development work in health care, aerospace, automotive and electronic
applications has continued.

Conflicts of Interest
The authors declare no conflicts of interest regarding the publication of this pa-
per.

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