RSC Advances
COMMUNICATION
A novel glycopolymeric ultraviolet absorber
covering UV-A and UV-B ranges†
Cite this: RSC Adv., 2014, 4, 22617
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Yanfeng Tang, Pengfei Gao, Miao Wang, Jinli Zhu and Xiangjian Wanb
*
Received 28th February 2014
Accepted 1st May 2014
DOI: 10.1039/c4ra01768d
In this communication, a novel biocompatible polymeric ultraviolet improved by introducing hydrophilic monomers, such as acrylic
absorber (UVA), poly(HAB-co-OAG-co-AMC) (PHOA), covering UV-A acid and its derivatives, polyethylene and glycol.
and UV-B ranges was designed and prepared. The photo-antioxidant
Herein, we aimed to (1) improve the biocompatibility of
tests indicate that there is a synergism between UV-A and UV-B polymeric UVA, and (2) cover both UV-A and UV-B ranges. As we
monomers. The cytotoxic experiments demonstrate that PHOA has all know, glucose as a carbohydrate has many advantages, i.e.
good biocompatibility.
outstanding biocompatibility, biodegradability and non-
toxicity.12–15 Hence, a novel glycopolymeric UVA was designed
and prepared through the linkage of UV-A, UV-B and glucosyl
monomers by radical copolymerization. The desired polymeric
UVA, poly(HAB-co-OAG-co-AMC) (PHOA), was characterized by
Introduction
1
The radiation emitted by the sun in the range from 100 to 400
nm is classied into UV-C (100–280 nm), UV-B (280–315 nm)
and UV-A (315–400 nm).1 Almost all UV-C radiation, which is
harmful to organisms, is absorbed by the higher layers of the
atmosphere,2,3 whereas UV-A and UV-B ranges can traverse
through the atmospheric layers. It was reported that the
excessive UV-B radiation could cause premature skin ageing,
sunburns, allergies and even skin cancer.4 However, UV-A
radiation is less harmful, and its overdose can also result in
similar effects as described above. Therefore, human skin has to
be protected against radiation of UV-A and UV-B types. The
studies of ultraviolet absorbers (UVAs) have attracted a great
deal of attention in recent years. To date, most reported UVAs
are small molecules, including benzophenone, cinnamate,
hindered amine and triazine.2,5–8
In general, these small molecules have excellent UV
absorption ability; however, they suffer from several drawbacks,
such as being readily absorbed by skin, being incompatible with
other composites and poor hydrophilicity. In order to overcome
these problems, polymeric UVAs have been developed.9–11 Not
only is the shortcoming of being absorbed easily by skin solved
due to increased molecular weight, but also incompatibility
with other ingredients and poor hydrophilicity are drastically
Fourier transform infrared (FT-IR) spectroscopy and H NMR.
Its UV absorption performance was investigated by UV-Vis
spectroscopy and photo-antioxidant tests. Cytotoxic activity
experiments were conducted to evaluate its biocompatibility.
UV-A monomer 2-hydroxy-4-acryloxy benzophenone (HAB)
was prepared according to the procedure described in a
previous study16 (Scheme 1a), and the UV-B monomer 4-(acryl-
oxy)methyl cinnamate (AMC) was synthesized by two steps
(Scheme 1b). PHOA was prepared from HAB, AMC and 3-O-allyl-
1,2,5,6-di-O-isopropynylene-a-D-glucose (OAIG) (Scheme 1c).
FT-IR spectra of poly(HAB-co-OAIG-co-AMC) (PHIA) and
PHOA are shown in Fig. 1. It is obvious that the strong peak at
3318 cmÀ1 can be assigned to the vibration of OH of the glycosyl
group. The presence of this peak reveals that the isopropyl
groups protecting the glycosyl ones were removed by hydrolysis
and PHOA was successfully prepared from PHIA. The peak at
about 1758 cmÀ1 is assigned to the vibration of the carbonyl
group (C]O). The peaks at 1629 cmÀ1, 1601 cmÀ1, 1506 cmÀ1
,
and 1445 cmÀ1 are ascribed to the absorption of aromatic rings,
and the absorption band at 1100–1250 cmÀ1 is the typical
vibration of C–O of the ester bond.
From the GPC spectrum (Fig. 2), it is found that the molec-
ular weight of PHOA is about 13 542. Only one peak in GPC and
FT-IR data shows that the three monomers have copolymerized
into PHOA.
The chemical structures of PHIA and PHOA were also char-
acterized by 1H NMR in d6-DMSO (Fig. 3). The spectrum of PHIA
exhibits the typical peaks of protected glycosyl groups at 1.31
aSchool of Chemistry and Chemical Engineering, Nantong University, Nantong 226019,
PR China. E-mail: jinlizhu@ntu.edu.cn
bSchool of Chemistry, Nankai University, Tianjian, 300071, PR China
† Electronic supplementary information (ESI) available: Details of experimental
operation, images and additional spectra. See DOI: 10.1039/c4ra01768d
This journal is © The Royal Society of Chemistry 2014
RSC Adv., 2014, 4, 22617–22620 | 22617
Tang, Yanfeng
