Poly(2-ethyl hexyl acrylate-co-methyl allyl polyethylene glycols ether–co-acrylic acid)

pressure-sensitive adhesives: Synthesis, Characterization, Investigations of Adhesive

and Thermal Properties
Berna Körpınara,b, Ece Atman Çaya, Hakan Akata*
a
Department of Chemistry, Faculty of Science, Ege University, 35100, Bornova, Izmir, Turkey
b
Department of Chemistry, Arts and Science Faculty, Celal Bayar University, 45140, Manisa, Turkey

*Corresponding Author: hakan.akat@ege.edu.tr, Tel:+902323888264

*Orcid Id: https://orcid.org/0000-0003-4002-5352
ABSTRACT

In the present study, solvent-based acrylic copolymers were successfully synthesized by

“solution polymerization” using methyl allyl polyethylene glycols ether, acrylic acid, and 2-
ethyl hexyl acrylate for the fabrication of high-performance pressure-sensitive adhesive tapes.
Different techniques (NMR, FTIR, TGA/DTG, Contact Angles, PSAs Test) were used to
characterize the physical and thermal properties of the copolymers. The obtained copolymers
were investigated as a possible adhesive for permanent or removable applications such as
security labels for power equipment, foil tape for HVAC ductwork, automotive interior trim
assembly, and sound/vibration dampening films. When the contact angles of the synthesized
copolymers were examined, it was observed that while the amount of acrylic acid in the
copolymer content was constant, the contact angle increased with the increase in the
percentage of HPEG. In addition, while the amount of HPEG was constant in the copolymers,
it was observed that the contact angle decreased with the increase in the percentage of acrylic
acid. As a result, it was determined that the obtained copolymers showed hydrophilic
character and wetted the contact surface. When the thermal properties of the copolymers were
examined, while the acrylic acid ratio was constant, the thermal stability increased with
increasing HPEG amount. While the HPEG ratio is constant in the copolymer content, the
decrease in thermal stability with increasing acrylic acid is thought to be due to
decarboxylation. Also, The 7 percent reduction in DTG curves is evidence of decarboxylation
of copolymers. According to the results of the pressure-sensitive adhesive test, it was
observed that the surface wetting degree of the copolymers changed in direct proportion to the
amount of acrylic acid increased and inversely proportional to the amount of HPEG, and the
potential of the adhesives obtained in addition to being high-performance pressure sensitive
adhesive tapes.

Keywords Solvent-based acrylic adhesive, Polyethylene Glycol Monomethylallyl Ether

(HPEG), acrylic acid, 2-ethylhexylacrylate(2-EHA), solution polymerization, PSAs

1. Introduction
Pressure-sensitive adhesives (PSAs) are a class of materials that can quickly adhere
to any surface under minimal pressure load. Pressure-sensitive adhesives (PSA) form a
strong bond with short contact times and under light pressure. PSAs adhere immediately
to a substrate (the material on which the PSA is applied) without the need for activating
agents(heat, water, solvent, etc.). Acrylic, silicone, polyurethane, or rubber-based
synthetic polymers are the preferred adhesive materials for use in commercial PSA
systems because of their excellent performance. Acrylics can be optimized for the
formulation of a PSA product by varying certain preparation parameters. Acrylics are
typically random copolymers of 2-ethylhexyl acrylate (2-EHA) with a short side chain and
low glass transition temperature (Tg) of n-butyl acrylate (BA), along with side-chain
acrylic, that sets Tg such as methyl acrylate and an acrylic acid (AA), which improves
adhesion to polar substrates and optimizes the elongation properties of the material. PSAs
can be applied as solvent-based, water-based (dispersions), or solvent-free systems[1].
Surface energy also affects the strength of the pressure-sensitive bond. Surface energy is a
measure of an adhesive's ability to wet and adhere to a surface[2]. Better wetting also
promotes surface penetration where microscopic surface irregularities can be filled to
produce adhesive locks that increase the strength of the mechanical bond[3,4]. Adhesives
with a lower FYE than the free surface energy (FYE) of a substrate will readily wet the
substrate surface and form strong adhesive bonds[5]. If adequate contact is maintained
between the substrate and the adhesive, physical interactions or bonds between the atoms
of the two surfaces will cause the surface to become wet. Wetting can be due to (a) acid-
base interactions, (b) the formation of weak hydrogen bonds, or (c) van der Waals forces
(dipole-dipole and dispersion forces).

Acrylic pressure-sensitive adhesives are divided into 3 types. These; are solvent-based,
water-based, and solvent-free acrylic adhesives. The solvent-based pressure-sensitive
adhesive market is developing rapidly and is finding a variety of uses. These adhesives are
frequently used in the production of single or double-sided tapes, labels, self-adhesive
bioelectrodes, decorative PVC markings, drug delivery systems and marking tapes[6,7]
Acrylic polymers consist of a combination of soft (with low Tg), hard (with high Tg)
functional monomers[8]. Soft monomers such as n-butyl, 2-ethylhexyl, n-octyl
acrylate[9,10] are effective in tack adhesion, which has the feature of sticking without
pressure and peel adhesion, which has the feature of peeling off the surface after applying
pressure. Hard monomers such as methyl and ethyl acrylate affect the cohesion properties
described as internal adhesion at the molecular level[11] Functional monomers such as
acrylic acid and acrylic amide contain a reactive moiety for crosslinking reactions. Acrylic
polymers are most widely used as PSA in commercial products such as tapes, labels, and
protective films due to their low cost, non-toxicity, transparency, and good weather
resistance[12]. Abusafieh et al synthesized a cross-linked poly(methyl methacrylate-
acrylic acid) copolymer, which may be suitable for potential bone implant applications.
They obtained this copolymer with a structure containing both hydrophobic and
hydrophilic components, which can swell by absorbing the water in the environment in a
controlled manner when left in the saltwater environment. They emphasized that the
degree of swelling depends on the volumetric ratio of hydrophilic acrylic acid and
hydrophobic methyl methacrylate and that the obtained copolymer can be used in bone
implants by absorbing body fluid and providing better adhesion to the implant[13].
Kotiyan et al synthesized a pressure-sensitive adhesive for drug delivery into the skin by
using 2-ethylhexyl acrylate and acrylic acid monomers by radical solution polymerization
method. It has been proven that the obtained adhesive is suitable for use to transport drugs
into the skin due to its compatibility with the skin[14]. Liu et al. obtained a series of
acrylate-based coating materials with high ink absorption and fast-drying properties
(MBAH) by emulsion copolymerization method using methacrylate (MMA), butyl
acrylate (BA), allyl polyethylene glycol (APEG) and hydroxyethyl methacrylate (HEMA).
They discussed and analyzed the effect of hydrophilic APEG in MBAH. They are then
covered with MBAH polyester fabric. In conclusion, their study showed the possibility of
obtaining a new acrylate copolymer with high ink absorption properties and the potential
application of a series of acrylate-based coating materials obtained as practical finishing
agents for inkjet printing[15]. Diakoumakos et al. aimed to find the conditions under
which oligomeric acrylic polyol resins with a low polydispersity (D= Mw/Mn) and
relatively low viscosity can be synthesized using the free radical polymerization method
to be used as a resin in solid content coatings. It has been emphasized that the obtained
resins have lower polydispersity and a certain molecular weight, showing better coating
film properties[16]. Lu et al synthesized poly(butyl acrylate-vinyl acetate-acrylic acid)
based acrylic pressure-sensitive adhesives (PSAs) by solution polymerization for the
production of high-performance pressure-sensitive adhesive tapes. The synthesized PSAs
have emphasized that they have high shear strength[17]. Kowaski et al investigated the
adhesion properties of cross-linked pressure-sensitive acrylic adhesive (PSA) using
aluminum acetylacetonate on various substrates such as stainless steel, glass,
polyethylene, polypropylene, polytetrafluoroethylene, polycarbonate, and poly(methyl
methacrylate). They emphasized that the obtained acrylic adhesive showed high
stickiness[18].

In this study, solvent-based acrylic copolymers were synthesized and the potential
of the synthesized copolymers as pressure-sensitive adhesives was investigated. The
effects of HPEG, EHA, and AA in different ratios used in copolymer synthesis on
molecular weight (Mw), polydispersity (Mw/Mn), contact angles, thermal stability, and
dependence of adhesive properties on copolymer composition were investigated. The
effectiveness of the ratio of monomers containing hydrophilic ends in the copolymer
composition on the adhesive property was discussed according to the results obtained. It is
thought that this study will be a data source about other acrylic-based pressure-sensitive
adhesives in the literature.

2. Experimental
2.1 Materials

2-Ethylhexyl Acrylate(2-EHA, 99%, Merck, Cas Number:103-11-7, USA), Acrylic Acid

(AA, 99%, Merck, Cas Number:79-10-07, USA), Polyethylene Glycol Monomethylallyl
Ether (HPEG, Cas Number: 27252-80-8 Norchem LLC), 2,2'-Azobisizobutyronitrile
(AIBN, 99%, Aldrich, Cas Number:78-67-1), Ethyl Acetate (99%, Merck, Cas Number:
141-78-6, USA), Methyl Alcohol (99%, Merck, USA).

2.2 Synthesis of Solvent-Based Acrylic Copolymers

The copolymers were synthesized by radical polymerization in ethyl acetate solvent

containing 1% AIBN initiator and different ratios of 2-EHA(75%), AA(10%), and
HPEG(15%) monomers. All copolymers obtained in the pure form were dried in a
vacuum oven and characterized. The copolymer compositions and the molecular weights
and polydispersity indexes of the obtained copolymers are given in Table 1.

2.3 Measurement Water Contact Angles of the pure water-copolymers interface

The water contact angle is the angle that meets the liquid-vapor boundary of a drop and
the solid surface. It measures the wettability of a solid surface by a liquid with the
Young's equation. The theoretical explanation of the contact is due to consideration of the
thermodynamic equilibrium between the three phases: liquid phase, solid phase, and gas
or vapor phase. Solid-vapor interface energy, solid-liquid interface energy, and liquid-
vapor interface energy then equilibrium contact angle is determined by Young's
equation[19,20]. The water contact angles of the pure water-copolymers interface were
measured with the help of the Attension Theta Flex Theta Optical Tensiometer device
according to ASTM D5946[21,22].

2.4 PSAs Test

Exact and suitable test methods for PSAs are needed to appoint that a given adhesive will
perform satisfactorily for its intended use. Characteristics of PSAs are categorized by peel
adhesion, cohesive strength, and tack. Tack is the dominant property of PSAs. To
determine the tack property, various testing methods are suggested, for example, rolling
ball tack test, probe tack test, and loop tack test. The loop tack test is one well-known
method. The ends of an adhesive strip are folded to form a teardrop shape. The bottom of
the loop is brought in contact with a rigid substrate at a constant rate until the contact
length in the longitudinal direction reaches a certain amount (usually 25.4mm). After a
short contact time (usually 1 sec), the top of the loop is brought upward at the same rate as
in the bonding phase until detachment occurs. The pulling force is recorded as a tack
curve[23]. The “Loop Tack” test is used to measure the tack force/strength of a pressure-
sensitive adhesive (PSA) according to ASTM D638-14. The "Loop Tack" test was used to
measure the bond strength/strength of pressure-sensitive adhesives (PSA) obtained
according to ASTM D638-14[24,25]. For this, loops were made with tapes with the label
on the outside of the loop. The ring universal tester is placed on the upper handle of the
machine. The loop was brought into contact with the 1 cubic inch fixed at the ‘12
inch/min speed’ of the universal testing machine. When the tape made contact with the
entire face of 1 on the square surface, its direction was reversed and the ring was pulled at
the same rate. The maximum force/stress required to remove the loop from 1 square
surface was recorded.

The peel test is the most commonly used method for measuring adhesion in flexible
packaging. The peel test comes in a variety of forms, varying in angle and apparatus.
Based on the practical consideration of the adhesive bond, peel tests are usually
determined at peel angles θ of 90° or 180° or in a T-peel configuration. The peel strength
is measured as the amount of force acting on the width of the bonding surface when
peeled at a constant velocity. The ‘Peel test is used for the peel adhesion of single-coated
adhesive tape when peeled at a 180 degree angle forpressure sensitive adhesive (PSA)
according to ASTM D3330. For this, test materials were prepared in a rigid layer such as a
few strips of tape and a metal plate to be tested. The tape was applied to the substrate with
even pressure using a hand-held roller. The tape was then pulled from the plate at a 180
degree angle at a given ratio and peel adhesion was measured[26].

3. Results and discussion

3.1 Characterization

The ‘solution polymerization technique’ is used in the synthetic approach for the direct
synthesis of polymers. The copolymers were successfully synthesized using solution
polymerization as seen in Fig.1. The spectrum obtained as a result of the 1H-NMR
analysis was evaluated (Fig. 2a-2b). While a singlet peak of around 4 ppm was observed
in the 1H-NMR spectrum of the copolymer without HPEG, a doublet peak was observed at
the same chemical shift value in the 1H-NMR spectrum of the copolymer containing
HPEG. The evidence that the synthesis of the copolymers desired to be synthesized was
carried out successfully was obtained.

Fourier transform infrared spectroscopy (FTIR) spectra of synthesized copolymers were

acquired using a PerkinElmer FTIR spectrometer. Fig. 3 shows FTIR spectra of the
copolymers. The FTIR absorption bands for C–H stretching of the copolymers take place
at 2850 and 2940 cm-1. While the characteristic strong absorption band of carbonyl and the
 ether group appears at 1720 cm-1 1170 cm-1 (C-O-C); C–H bending appears at 1380 cm-1.
Looking at Fig. 2, the peak of C=C sp2 hybridization on the straight chain, which is
present in both acrylic acid, HPEG, and 2-EHA is seen at about 1600 cm -1 and is not
visible after copolymers synthesis.

Molecular weights and polydispersities of the linear polymers were determined by gel
permeation chromatography (GPC) using a Viscotek GPC max autosampler system
consisting of a pump, three ViscoGEL GPC columns (G2000HHR, G3000HHR, and
G4000HHR), a Viscotek UV detector, and a Viscotek differential refractive index (RI)
detector with THF as eluent at a flow rate of 1.0 mL/min at 30 °C. As the molecular
weights of the obtained copolymers were compared, the highest molecular weight was
found in Experiment 5 containing 2-EHA:AA:HPEG at 75:5:20 ratios, and the lowest
molecular weight in Experiment 15 containing 70:10:20 ratios. The polydispersities of the
copolymers were determined as 2.12 and 3.99, respectively. In addition, when Table 1 is
examined, it was seen that the polydispersity of the copolymers decreases with the
increasing amount of HPEG in the copolymer content, and as a result, the polymer chain
lengths are equal or close to each other. On the other hand, the increasing amount of
acrylic acid in the copolymer composition decreased the polydispersity.

Table 1. Copolymer compositions, molecular weight, and polydispersity

Copolymer compositions Molecular Weight Polydispersity

EHA:AA:HPEG Mw Mn Mw/Mn
Exp. 1 90:10:0 83045 22028 3.77
Exp. 2 90:5:5 93350 29081 3.21
Exp. 3 80:10:10 44648 12830 3.48
Exp. 4 70:10:20 47730 13835 3.45
Exp. 5 75:10:15 238910 71961 3.32
Exp. 6 80:5:15 119500 29950 3.99
Exp. 7 85:5:10 93350 29081 3.21
Exp. 8 85:10:5 85417 24405 3.50
Exp. 9 75:5:20 81093 21625 3.75
Exp. 10 95:5:0 92408 23634 3.91
Exp. 11 95:0:5 148561 70076 2.12
Exp. 12 90:5:5 114008 37751 3.02
Exp. 13 85:10:5 63865 20535 3.11
Exp. 14 80:15:5 54739 16895 3.24
Exp. 15 80:20:0 44380 12864 3.45

Fig. 1 Synthesis of solvent-based Acrylic copolymers via radical polymerization

Fig. 2 NMR spectrum of copolymers with HPEG(2a), without HPEG (2b)

 Fig.3 FT-IR spectra of all copolymers

The thermal stability of obtained copolymers was investigated using thermogravimetric

analysis. TG measurements of polymer samples were obtained on PerkinElmer Diamond
TA/TGA between 25 and 600 °C at a constant heating rate of 10 °C/min in a 100 mL/min
nitrogen atmosphere. When TGA and DTG thermograms(Fig. 4a,4b,) are examined while
the acrylic acid ratio was constant, the thermal stability increased with increasing HPEG
amount. While the HPEG ratio is constant in the copolymer content, the decrease in
thermal stability with increasing acrylic acid is thought to be due to decarboxylation. Also,
the 7 percent reduction in DTG curves(Fig.5a,5b) is evidence of decarboxylation of
copolymers. Also, ıt was observed that the maximum degradation rates increased with the
increase in the amount of acrylic acid in the copolymer content, while the increase in the
amount of HPEG did not affect the change in the maximum degradation rates.
Fig. 4a TGA thermogram of copolymers with an increased ratio of HPEG

Fig. 4b TGA thermogram of copolymers with an increased ratio of AA

Fig. 5a DTG curve of copolymers with an increased ratio of HPEG

Fig. 5b DTG curve of copolymers with an increased ratio of AA

The contact angles of the pure water-copolymer interface were measured with the help of
the Attension Theta Flex Theta Optical Tensiometer device. When the contact angles of
the synthesized copolymers(Table 2) were examined, it was observed that while the
amount of acrylic acid in the copolymer content(Fig.6) was constant, the contact angle
increased with the increase in the percentage of HPEG. In addition, while the amount of
HPEG was constant(Fig.7) in the copolymers, it was observed that the contact angle
decreased with the increase in the percentage of acrylic acid. As a result, it was
determined that the obtained copolymers showed hydrophilic character and wetted the
contact surface.

Table 2. Contact Angles of the pure water-copolymers interface

Experiment AA HPEG 2-EHA Average Contact Angle

1 10 0 90 17,5
13 10 5 85 52,4

3 10 10 80 63,1

5 10 15 75 72,7

4 10 20 70 107,6

11 0 5 95 24,2 
12 5 5 90 40,4

8 10 5 85 52,4

14 15 5 80  63,1

15 20 5 75  86,9

10 5 0 95  8,9
2 5 5 90 22,8

7 5 10 85 40,4

6 5 15 80 59,1

9 5 20 75 74
 Fig. 6 Average Contact Angles images of exp.1,2,3,4,5 with an increased ratio of HPEG

Fig. 7 Average Contact Angles images of exp. 6,7,8,9,10 with an increased ratio of AA

3.2 PSAs Test

The loop tack test of synthesized copolymers was acquired using loop tack devotrans
DVT BPD NN 200N device, which is a single column model used in capacities up to 3
kN. The Peel test of obtained copolymers was acquired using PA-1000-180 180° Peel
Adhesive Testing Machine. Loop tack and Peel adhesion test results of synthesized
polymers are given in Table 3a-3b. When the table is examined, the best loop tack and
peel result was obtained in Trial 12 containing AA:HPEG:2-EHA at 10:5:85 ratios. It
was observed that the surface wetting degree of the copolymers changed inversely
with the increasing amount of HPEG.
Table 3a. Loop Tack-Peel Test result when HPEG amount is constant in the
copolymer composition

 Copolymer Composition Experiment 6 Experiment 12 Experiment 10

AA 0 10 20
HPEG 5 5 5
2-EHA 95 85 75
Loop Tack(N)
0.5/0.8 17.4/21.4 1.2/0.8
/Peel (N/25 mm)

Table 3b. Loop Tack-Peel Test result when AA amount is constant in the copolymer
composition

Copolymer Composition  Experiment 1 Experiment 3 Experiment 5

AA 5 5 5
HPEG 0 10 20
2-EHA 95 85 75
Loop Tack(N)/Peel (N/25
1.83/10.7 0.75/3.3 0.5/3.5
mm)

When the loop tack and peel tests of copolymers are compared with the studies in the
literature Marquez et al obtained a peel result in the range of 7-15 N/25mm and a tack
result in the range of 7-27 N/25mm[27]. Zhang et al obtained peel results in the range
of 3.5-19 N/25mm with 2-EHA, MMA, BA, and HPA monomers[28]. Czech et al
obtained peel values in the range of 1.6-21.5 N/25mm with 2-EHA, AA, EAcr, MA
monomers[29]. Zhu et al 2020 obtained 14.78-19.39 N/25mm tack, 18.64-22.68 N/25
mm peel results with BA, HEA, and AA monomers and in the presence of HDDA
crosslinker[30]. Tobing et al obtained 2.625-8.325 N/25 mm 90⁰ peel in the adhesive
synthesized by solution polymerization technique with BA and AA monomers, and
3.95-5.25 N/25mm 90⁰ peel in the adhesive synthesized by emulsion polymerization
with the same amount and same monomers[31].
4. Conclusion

Poly(2-ethyl hexyl acrylate-co-methyl allyl polyethylene glycols ether-co-acrylic

acid) pressure-sensitive adhesives were synthesized by solution polymerization. Different
techniques (NMR, FTIR, TGA/DTG, Contact Angles, PSAs Test) were used to
characterize the physical and thermal properties of the copolymers. The effects of HPEG,
EHA, and AA in different ratios used in copolymer synthesis on molecular weight (Mw),
polydispersity (Mw/Mn), contact angles, thermal stability, and dependence of adhesive
properties on copolymer composition were investigated. It was observed that the contact
angle decreased with the increasing amount of AA, and the contact angle increased with
increasing HPEG ratio in the composition of the copolymers. According to the TGA/DTG
curves of copolymers, while the acrylic acid ratio was constant, the thermal stability
increased with increasing HPEG amount. However, the thermal stability of the
copolymers decreased as decarboxylation occurred with an increasing amount of AA. It
was observed that increasing the amount of both AA and HPEG in the copolymer
composition increased the molecular weight. When the loop tack and peel table tables of
the copolymer are examined, the best loop tack and peel result was obtained in experiment
12 containing AA:HPEG:2-EHA at 10:5:85 ratios.

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