Synthesis of Photosensitive Cyclopropane-Containing Polymers

Article abstract of DOI:10.1134/S1070427219090052

New cyclopropyl methacrylate monomers were prepared, their radical polymerization was performed, and the composition and structure of the polymers obtained, containing reactive UV-sensitive fragments, were determined. Experiments on photochemical cross-li

Full text of DOI:10.1134/S1070427219090052

ISSN 1070-4272, Russian Journal of Applied Chemistry, 2019, Vol. 92, No. 9, pp. 1215−1222. © Pleiades Publishing, Ltd., 2019.
Russian Text © The Author(s), 2019, published in Zhurnal Prikladnoi Khimii, 2019, Vol. 92, No. 9, pp. 1131−1139.
MACROMOLECULAR COMPOUNDS
AND POLYMERIC MATERIALS
Synthesis of Photosensitive Cyclopropane-Containing Polymers
K. G. Guliyeva,*, A. E. Rzayevaa, and A. M. Guliyeva
a Institute of Polymer Materials, National Academy of Sciences of Azerbaijan, Sumgayit, Az5004 Azerbaijan
*e-mail: ipoma@science.az
Received November 20, 2018
Revised April 15, 2019
Accepted July 5, 2019
Abstract—New cyclopropyl methacrylate monomers were prepared, their radical polymerization was performed,
and the composition and structure of the polymers obtained, containing reactive UV-sensitive fragments, were
determined. Experiments on photochemical cross-linking revealed photosensitivity of the polymers synthesized.
The materials based on them are optically transparent and can be used in microelectronics and optics.
Keywords: cyclopropane, photosensitivity, optical transparency, phenyl-substituted cyclopropyl methacrylate
DOI: 10.1134/S1070427219090052
Macromolecules containing various photoreactive
fragments in macrochains exhibit a valuable set of
properties. Such polymers can be cross-linked under the
action of radiation, which allows preparation of resists
for microelectronics. Therefore, preparation of new
types of photosensitive polymers for microelectronics
attracts much attention of researchers [1–5].
EXPERIMENTAL
The IR spectra of the polymer films were determined
with an AgilentCary 630 FTIR device, and the Н
1
NMR spectra, with a Bruker AFR-300 spectrometer in
CDCl3; the chemical shifts were determined relative
to tetramethylsilane. The purity of the compounds
synthesized was checked by gas–liquid (GLC) and thin-
layer (TLC) chromatography. The GLC analysis was
performed with LKhM-8 MD (model 3) and Tsvet-100
chromatographs. Apiezon-L (15%), XE-60 (5%), and
poly(ethylene glycol adipate) (PEGA) (5%) were used
as liquid phases. The supports were Chromaton and
Celite-547; the carrier gas was helium. TLC analysis was
performed using glass plates of sizes 60 × 130, 130 ×
180, and 230 × 300 mm with 1–2 mm thick unfixed SiO2
layer and Silufol UV plates of sizes 30 × 60 and 160 ×
160 mm with the fixed adsorbent layer.
Polymers containing cyclopropane units with various
functional substituents in macromolecules are of much
interest, because they exhibit a balanced set of properties,
including photosensitivity and optical transparency, and
can be used in polymer resists and optically transparent
materials in microelectronics and optics. One of the
ways of preparing polymers containing cyclopropane
units with reactive functional groups is polymerization
of new monomers [6–9].
In this study, we prepared new cyclopropane-con-
taining methacrylate monomers, analyzed the relation-
ships of their radical polymerization, and determined
the properties of the polymer samples obtained.
The purity of all the starting compounds was 98–
99.9%. The starting compounds had the following
characteristics: styrene (Acros Organics), bp 145°С,
nD20 1.5462, d420 0.9090; p-chlorostyrene (Alfa Aesar),
We suggested a new strategy of the synthesis of
functionally substituted polymethacrylate with pendant
functional cyclopropane fragments, capable of forming
photosensitive elastic films. We also studied the struc-
ture and properties of the polymers with the aim of de-
veloping new photosensitive and transparent polymers.
bp 191–192°С, nD20 1.5650, d4 1.0868; p-nitrostyrene
20
(Alfa Aesar), bp 93–96°С, nD20 1.5753, d420 1.1632;
ethyl diazoacetate (synthesized by us), bp 140–
141°C, nD20 1.4610, d420 1.085; methacryloyl chloride
(synthesized by us), bp 95–96°C, nD20 1.4420, d420 1.070.
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GULIYEV et al.
1216
Reaction of ethoxycarbonylcarbene with phenyl-
(0.25 mol) of ethyl 2-phenylcyclopropanecarboxylate
was added over a period of 2.0–2.5 h. The temperature
of the reaction medium was maintained in the range
25–35°С. After the whole amount of the ester was
added, the mixture was stirred for an additional 30 min.
After that, distilled water and then 5% HCl were added
dropwise. The ether layer was separated, and the aqueous
layer was extracted with ether (2 × 20 mL). The ether
extracts were combined with the ether layer and dried
over calcined Na2SO4. After distillation of the diethyl
ether, the products were isolated by vacuum distillation.
Compounds 5 and 6 were prepared similarly.
substituted styrenes. A mixture of 0.6 mol of styrene
or p-phenyl-substituted styrene and 0.2 g of anhydrous
copper sulfate (catalyst) was heated to 40–50°С, and
0.5 mol of ethyl diazoacetate was added dropwise with
stirring at a rate of 10–12 g h–1.After the whole amount of
ethyl diazoacetate was added and the nitrogen evolution
ceased, the mixture was cooled to room temperature.
The catalyst (СuSO4) was filtered off and extracted
several times with diethyl ether, and the organic phases
were combined. Then, the ether was distilled off, and
the residue was distilled in a vacuum. The first fraction
contained excess styrene or phenyl-substituted styrene,
and then the main fraction (products 1–3) was distilled.
The IR spectra of 4–6 contain absorption bands in
the ranges 3095–3100 (νС–Н ring); 2980, 2940, 2880
(νС–Н aliph); 2900–3100 cm–1 (ОН).
The IR spectra of 1–3 contain absorption bands at
3095–3100, 1030–1035 (νС–H ring); 2980, 2940, 2880
(νC–H aliph), 750–760 (νC–Cl); 1690, 1720 (νC=O); 1450–
1500; 1570–1620, 1335, and 1525 cm–1 (NO2, for 3);
and out-of-plane C–H bending vibration bands of
monosubstituted benzene at 690–750 cm–1 for 1.
2-Phenyl-1-hydroxymethylcyclopropane (4). Yield
92%, bp 125–130°С (9 mm Hg), nD20 1.5110, d420 1.335,
1
МRD = 43.235. Н NMR spectrum, δ, ppm: 6.92 m
(5Нarom), 1.93 m (1Н, СHcyclopropane), 2.61 m (1Н,
СHcyclopropane), 1.63 m (1Н, СН2cyclopropane), 1.65 m (1Н,
СН2cyclopropane), 3.86 d (2Н, СН2О), 3.64 s (1Н, ОН).
Found, %: С 81.25, Н 8.05. С10H12O. Calculated, %:
С 81.08, Н 8.10.
2-Phenyl-1-ethoxycarbonylcyclopropane (1). Yield
90%, bp 68–70°С (3 mm Hg), nD20 1.5125, d420 1.08.
1Н NMR spectrum, δ, ppm: 6.95 m (5Нarom), 1.92 m
(1Н, СHcyclopropane), 2.56 m (1Н, СHcyclopropane), 1.65 m
(1Н, СН2cyclopropane), 1.62 m (1Н, СН2cyclopropane), 3.85 q
(2Н, СН2), 0.96 t (3Н, СН3). Found, %: С 75.20, Н 7.91.
С12H14O2. Calculated, %: С 75.79, Н 7.37.
2-p-Chlorophenyl-1-hydroxymethylcyclopropane
(5). Yield 94%, bp 135–142°С (9 mm Hg), nD20 1.5225,
1
d420 1.478, МRD = 48.998. Н NMR spectrum, δ, ppm:
7.14 m (4Нarom), 2.05 m (1Н, СHcyclopropane), 2.57 m
(1Н, СHcyclopropane), 1.66 m (1Н, СН2cyclopropane), 1.72 m
(1Н, СН2cyclopropane), 3.91 d (2Н, СН2О), 3.68 s (1Н,
ОН). Found, %: С 65.20, Н 6.75, Сl 19.94. С10H11OСl.
Calculated, %: С 65.75, Н 6.03, Сl 19.45.
2-p-Chlorophenyl-1-ethoxycarbonylcyclopropane
(2). Yield 82%, bp 85–87°С (3 mm Hg), nD20 1.5640,
1
d420 1.32. Н NMR spectrum, δ, ppm: 7.10 m (4Нarom),
2.08 m (1Н, СHcyclopropane), 2.55 m (1Н, СHcyclopropane),
1.71 m (1Н, СН2cyclopropane), 1.65 m (1Н, СН2cyclopropane),
4.0 q (2Н, СН2), 1.0 t (3Н, СН3). Found, %: С 64.28,
Н 5.32, Сl 15.75. С12H13O2Cl. Calculated, %: С 64.14,
Н 5.79, Cl 15.81.
2-p-Nitrophenyl-1-hydroxymethylcyclopropane (6).
Yield 93%, bp 131–149°С (2 mm Hg), nD20 1.5190,
1
d420 1.524, МRD= 49.998. Н NMR spectrum, δ, ppm:
7.55 m (4Нarom), 2.17 m (1Н, СHcyclopropane), 2.60 m (1Н,
СHcyclopropane), 1.65 m (1Н, СН2cyclopropane), 1.69 m (1Н,
СН2cyclopropane), 3.98 d (2Н, СН2О), 3.71 s (1Н, ОН).
Found, %: С 62.22, Н 5.40, N 7.80. С10H11O3N.
Calculated, %: С 62.18, Н 5.69, N 7.25.
2-p-Nitrophenyl-1-ethoxycarbonylcyclopropane
(3). Yield 65%, bp 140–142°С (3 mm Hg), nD20 1.5610,
1
d420 1.30. Н NMR spectrum, δ, ppm: 7.50 m (4Нarom),
2.09 m (1Н, СHcyclopropane), 2.68 m (1Н, СHcyclopropane),
1.67 m (1Н, СН2cyclopropane), 1.63 m (1Н, СН2cyclopropane),
4.13 q (2Н, СН2), 1.12 t (3Н, СН3). Found, %: С 61.11,
Н 5.63, N 5.80. С12H13O4N. Calculated, %: С 61.28,
Н 5.53, N 5.95.
Synthesis of 2-p-phenyl-substituted cyclopropylme-
thyl methacrylates. A flask equipped with a reflux con-
denser was charged with 0.5 mol (74 g) of 2-phenyl-
1-hydroxymethyl cyclopropane and heated in pyridine
at 40°С for 2 h, after which 0.6 mol of methacryloyl
chloride in 30 mL of absolute benzene was added drop-
wise. After the reaction completion, the liquid phase was
separated and dried, the light fractions were distilled off,
Synthesis of 2-p-phenyl-substituted 1-hydroxymethyl-
cyclopropanes. A 500-mL three-necked flask equipped
with a power-driven stirrer, a dropping funnel, and a
reflux condenser was charged with 9.1 g (0.25 mol) of
LiAlH4 in 200 mL of absolute diethyl ether, and 85 g
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SYNTHESIS OF PHOTOSENSITIVE CYCLOPROPANE-CONTAINING POLYMERS
1217
and the main fraction was distilled in a vacuum. Com-
pounds 8 and 9 were prepared similarly.
off, avoiding the film peel-off. The photoresist thickness
wasmeasuredwithanMII-4Linnikmicrointerferometer.
The resist film thickness after drying for 10 min at room
temperature and then for 20 min at 25°C/10 mmHg was
0.2–0.3 μm.
The IR spectra of 7–9 contain absorption bands at
1435–1440, 3095–3100 (νС–Н ring), 2880, 2940, 2980
(νС–Н aliph), 750–760 (νC–Cl), 1365 and 1335 cm–1 (NO2).
The pieces with the deposited photoresist were
exposed on an installation with a point light source
through a phototemplate.
2-Phenylcyclopropylmethyl
methacrylate
(7).
Yield 95%, bp 95–110°С (3 mm Hg), nD20 1.4040,
1
d420 0.878, МRD = 60.027. Н NMR spectrum, δ, ppm:
7.25 m (5Нarom), 1.91 m (1Н, СHcyclopropane), 2.58 m (1Н,
СHcyclopropane), 1.58 m (1Н, СН2cyclopropane), 1.60 m (1Н,
СН2cyclopropane), 4.08 d (2Н, СН2О), 5.48 s (1Н, СН2vinyl),
5.89 s (1Н, СН2vinyl), 1.57 s (3Н, СН3–С=). Found, %:
С 77.45, Н 7.83. С14H16O2. Calculated, %: С 77.78, Н 7.40.
The development was performed in a jet installation.
A 1 : 2 mixture of dioxane with isopropyl alcohol at 18–
25°С was used as a developer. The extent of the photo-
chemical polymerization (cross-linking) of photoresist
base molecules under UV irradiation served as a crite-
rion of the photosensitivity of the negative photoresists.
2-p-Chlorophenylcyclopropylmethyl methacrylate
(8). Yield 96%, bp 110–115°С (3 mm Hg), nD20 1.4105,
A DRT-220 mercury lamp was used as a UV radiation
source (current 2.2 А, distance from the radiation source
15 cm, velocity of the exposure meter shutter 720 mm h–1,
exposure time 5–20 s). The content of the insoluble poly-
mer was calculated from the residue weight.
1
d420 0.970, МRD = 63.787. Н NMR spectrum, δ, ppm:
7.36 m (4Нarom), 1.88 m (1Н, СHcyclopropane), 2.63 m
(1Н, СHcyclopropane), 1.58 m (1Н, СН2cyclopropane), 1.64 m
(1Н, СН2cyclopropane), 4.11 d (2Н, СН2О), 5.49 s (1Н,
СН2vinyl), 5.92 s (1Н, СН2vinyl), 1.66 s (3Н, СН3–С=).
Found, %: С 67.24, Н 5.57, Сl 14.81. С14H15O2Сl. Cal-
culated, %: С 67.07, Н 5.98, Сl 14.17.
The photosensitivity is a quantity reciprocal to the
UV dose absorbed by the photoresist, i.e., to the dose
required for converting the photoresist to the insoluble
state. It is measured in cm2 W–1 s–1 = cm2 J–1:
2-p-Nitrophenylcyclopropylmethyl
methacrylate
(9). Yield 94%, bp 117–125°С (3 mm Hg), nD20 1.4080,
1
d420 0.950, МRD = 67.585. Н NMR spectrum, δ, ppm:
7.60 m (4Нarom), 2.18 m (1Н, СHcyclopropane), 2.70 m (1Н,
СHcyclopropane), 1.66 m (1Н, СН2cyclopropane), 1.72 m (1Н,
СН2cyclopropane), 4.22 d (2Н, СН2О), 5.66 s (1Н, СН2vinyl),
6.01 s (1Н, СН2vinyl), 1.89 s (3Н, СН3–С=). Found, %:
С 64.73, Н 5.18, N 5.66. С14H15O4N. Calculated, %:
С 64.36, Н 5.75, N 5.36.
where H is the exposure (or UV irradiation dose) (J cm);
E, intensity (W cm–2); and τ, irradiation time (s).
RESULTS AND DISCUSSION
To cross-link the copolymers, we prepared 2–10%
polymer solutions and applied them onto a 60 × 90 mm
glass support by centrifugation at 2500 rpm. After that,
the photoresist was kept for no less than 20 min to
enhance its adhesion to the support. Then, the parts of the
photoresist film protruding beyond the support were cut
First, we studied the compounds formed by the
reactions of ethoxycarbonylcarbene with styrene
and p-substituted styrenes under the conditions of
thermocatalytic decomposition of ethyl diazoacetate in
the presence of anhydrous CuSO4 (Scheme 1).
Scheme 1.
R = H (1, 4), Cl (2, 5), NO2 (3, 6).
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GULIYEV et al.
1218
Scheme 2.
δ, ppm
δ, ppm
δ, ppm
δ, ppm
Fig. 1. NMR spectra of the synthesized compounds: (1) 2-phenyl-1-ethoxycarbonylcyclopropane, (2) 2-phenyl-1-
hydroxymethylcyclopropane, (3) 2-phenylcyclopropylmethyl methacrylate, and (4) poly(2-phenylcyclopropylmethyl methacrylate).
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SYNTHESIS OF PHOTOSENSITIVE CYCLOPROPANE-CONTAINING POLYMERS
1219
The IR spectra and GLC data show that the
compounds synthesized are mixtures of two geometric
isomers, cis and trans (relative to the three-membered
ring); the ratio of these isomers is trans : cis = 70 : 30.
The product purity was checked by GLC and was higher
than 99.2% in all the cases.
Phenyl and p-substituted phenyl derivatives of
cyclopropylmethyl methacrylate (7–9) were prepared
by the reaction in Scheme 2.
The radical polymerization was performed in the bulk
and in a benzene solution in sealed ampules at 70°С in
the presence of azobis(isobutyronitrile) (AIBN) (0.3%
relative to the monomer weight). The polymers obtained
are white powders soluble in aromatic and chlorinated
hydrocarbons and insoluble in aliphatic hydrocarbons
Time, min
and lower alcohols.
Fig. 2. Conversionasafunctionofthepolymerizationtime.The
curve nos. are compound nos.: (7) 2-phenylcyclopropylmethyl
methacrylate, (8) 2-p-chlorophenylcyclopropylmethyl meth-
acrylate, (9) 2-p-nitrophenylcyclopropylmethyl methacrylate,
and (А) p-chlorophenyl methacrylate.
The structure of the polymers obtained was deter-
mined by IR and NMR spectroscopy and by elemental
analysis. The IR spectra of the polymers contain the car-
bonyl absorption bands at 1730 cm–1, compared to 1720
cm–1 in the spectra of the initial monomers. The shift of
the C=O absorption maximum is due to opening of the
double bond with the break of the conjugation and elec-
tron density redistribution in the system.
on the polymerization time under the chosen standard
conditions. Figure 2 shows the kinetic curves of the
polymerization of monomers 7–9 and p-chlorophenyl
methacrylate (А). The polymerization of chlorophenyl
methacrylate occurred in the bulk at 70°С under similar
conditions. Comparison of the kinetic curves shows
that the synthesized monomers 7–9 and p-chlorophenyl
methacrylate appreciably differ in the polymerization
In the spectra of the polymers obtained from
monomers 7–9, the stretching and bending vibrations of
the benzene rings are observed at 1608, 1580, 1496, and
1456 cm–1. The absorption bands at 1035–1040 cm–1,
observed in the IR spectra of both the monomers and
polymers, can be assigned to cyclopropane groups. The
bands in the regions of 900–1000 and 1640–1645 cm–1,
belonging to bending and stretching vibrations of the
vinyl double bond and observed in the spectra of the
monomers, disappear in the spectra of the polymers.
In the NMR spectra of the polymers (Fig. 1), there are
well-defined proton signals of the benzene (δ = 6.80–
7.60 ppm) and cyclopropane (δ = 0.25–2.60 ppm) rings;
the vinyl proton signals (δ = 4.50–5.05 ppm) are absent
in the spectra of the polymers.
Thus, the spectroscopic analysis shows that the
polymerization occurs exclusively via the double bond
of the vinyl group, with the pendant reactive fragments
λ, nm
(
) remaining unchanged.
Fig. 3. UV spectra of the synthesized compounds. The curve
nos. are compound nos.: (7) 2-phenylcyclopropylmethyl
methacrylate,
(8)
2-p-chlorophenylcyclopropylmethyl
To evaluate the polymerization ability of monomers
7–9, we studied the dependence of the polymer yield
methacrylate, and (9) 2-p-nitrophenylcyclopropylmethyl
methacrylate.
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GULIYEV et al.
1220
ability and can be ranked in the following order: А > 9 >
8 > 7. This fact is probably associated with the effect
of the chlorophenyl group via O atom on the carbonyl
group conjugated with the vinyl moiety.
is due to the presence of such strongly absorbing groups
as
, which enhance the UV
The observed order of the monomer activity in radical
polymerization is not directly associated with the conju-
gation effect, although the UV spectra (Fig. 3) of these
monomers demonstrate changes in the absorption band.
Probably, steric factors play an important role in the chain
propagation step. The relative stability of the radical re-
sponsible for the chain propagation can be another impor-
tant factor influencing the course of the polymerization.
sensitivityofthepolymerandarepronetophotochemical
transformations leading to the polymer chain cross-
linking. The carbonyl group is the main functional group
in the polymer. The polymer contains various absorbing
groups such as (
), Cl, and (
).
Therefore, such polymers should be photosensitive. The
UV irradiation of the polymer films leads to opening
of the cyclopropane rings and their recombination with
the probable formation of the cyclohexane ring acting
as a cross-linking group. In the process, the polymer
becomes insoluble. Presumably, the reaction occurs by
the mechanism described in [1, 11].
As we found, the radical polymerization of all
the monomers in the bulk is accompanied by self-
acceleration. The onset of the self-acceleration is
observed at ~25% conversion of the monomers, in
agreement with the data of [10].
The synthesized polymers containing UV-sensitive
reactive groups are valuable objects for photochemical
studies and can serve as a basis for the development
of photosensitive materials. The presence of reactive
groups in the polymer macromolecules makes it
interesting to study the photochemical cross-linking of
the polymer under the action of UV radiation. Intense
occurrence of photochemical processes in the polymer
The cross-linking of macromolecular chains under
the action of actinic radiation occurs considerably faster
than the oxidation. We performed experiments with
different polymer concentrations in thin films. The UV
spectra of the polymer films contain absorption bands
at ~275 and ~285 nm. To determine the pathways
and mechanism of the photochemical reaction, we
Scheme 3.
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SYNTHESIS OF PHOTOSENSITIVE CYCLOPROPANE-CONTAINING POLYMERS
1221
ν, cm–1
Fig. 4. IR spectra of the poly(2-phenylcyclopropylmethyl methacrylate) film, (1) unirradiated and irradiated for (2) 5, (3) 10, and
(4) 25 s.
studied the IR spectra (Fig. 4) in various steps of the
UV irradiation. The UV irradiation leads to a decrease
in the intensity and then to the disappearance of the
absorption bands at 1720 and 1035 cm–1, corresponding
to the carbonyl and cyclopropane groups in the pendant
chains of the macromolecule. This fact suggests that the
photochemical cross-linking occurs via opening of the
cyclopropane ring with the participation of the carbonyl
group. Our studies demonstrate the possibility of the
synthesis of a new valuable photosensitive polymer
(35–40 cm2 J–1) as a base of a photosensitive material.
The film thickness is an important factor in irradiation.
Good results were obtained in experiments with 0.2–
0.3 μm thick films. After irradiation for 30–80 s (40–
75% conversion), the polymer films become insoluble
in organic solvents in which they dissolved at room
temperature before irradiation.
The synthesized polymers can be used as
photosensitive polymer materials, and also in optics as
optically transparent materials.
CONCLUSIONS
(1) New polyfunctional monomers, cyclopropyl
methacrylates, were synthesized, their radical homopo-
lymerization was performed, and the composition and
structure of the polymers based on the corresponding
monomers was determined.
(2) UV-induced cross-linking of the polymers was
studied. The synthesized polymers exhibit relatively
high photosensitivity (35–40 cm2 J–1) and are good
optically transparent materials.
CONFLICT OF INTEREST
The authors declare that they have no conflict of interest.
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The synthesized polymers also have good optical
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