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Synthesis and Biocompatibility of New Contact Lenses Based On Derivatives

of 2-Hydroxy Ethyl Meth Acrylate and 2-Ethyl Hexyl Methacrylate

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International Journal of Research Studies in Biosciences (IJRSB)
Volume 3, Issue 3, March 2015, PP 1-9
ISSN 2349-0357 (Print) & ISSN 2349-0365 (Online)
[Link]

Synthesis and Biocompatibility of New Contact Lenses Based

On Derivatives of 2-Hydroxy Ethyl Meth Acrylate and 2-Ethyl
Hexyl Methacrylate
[Link] A. Muter
Chemistry Department
College of Education University of Al-Qadisiya, Iraq
mohammeddw73@[Link]

Abstract: In the contact lens industry, copolymerization is extensively used in the synthesis of hydrogel
materials .Almost all hydrogel materials are copolymers. By polymerizing various combinations of
monomers, the physical and chemical properties of a lens can be modified. This work describes the
synthesis of new soft contact lenses based on2-hydroxyl ethyl methacrylate (HEMA) and 2-ethylhexy
methacrylate (EHMA) monomers by free radical polymerization in the presence of ethylene glycol
dimethacrylate (EGDMA) and 1, 6-Hexanediol diacrylate (HDODA) as a crosslinking agent and benzoyl
peroxide as an initiator. FTIR was performed to find out the total conversion of HEMA and EHMA
monomers into a hydrogel contact lens.
The swelling was measured for all the hydrogels at 34°C, and it found that the hydrophilic hydrogels
swelling more than hydrophobic hydrogels. Oxygen permeability (DK) was measured by Morgan &Efron
equation, the results show, the hydrophilic hydrogels display higher oxygen permeability towards the
cornea more than hydrophobic hydrogels. The amount of proteins adsorbed on the membrane surface of
hydrogels contact lenses was calculated, the results show that albumin deposits in higher concentrations on
hydrophobic surfaces, with comparison to relatively hydrophilic surfaces. The transparency of all hydrogel
was examined using UV-visible spectrophotometer and the results show that all hydrogel contact lenses
allow range of light transmittance 57-94.6%, at wavelengths between 400-700 (nm).
Keyword: Hydrogel, Contact lenses, Oxygen permability, Proteinadsorption, Transmittance
measurement, swelling.

1. INTRODUCTION
Contact lenses are defined as thin curved disks made out of a clear material and can be classified
in a number of ways, yet the two main categories are the hard and the soft lenses depending on the
material used for their manufacture. A further division of the soft lens category can be made into
two sub categories, hydrophobic and hydrophilic sub categories. Thus, the development of contact
lens materials takes three specific directions. The first is that hydrogel with high water content,
the second is the rigid gas-permeable lenses with enhanced oxygen permeability's. And the third,
surface is the modification of silicone elastomer lenses. Such polymeric systems are expected to
improve the water content of the contact lenses and the permeability to oxygen as well [Garrett et
al. 2002].
Copolymerization in contact lenses' industry is extensively used in the synthesis of materials.
Almost all hydrogel materials are copolymers. The physical and chemical properties of a lens can
be modified polymerizing various combination of monomers. Also, through varying the ratio of
the same two monomers, materials can be created having various water contents, refracture
indices, hardness, mechanic strengths and oxygen permeability as well. Many varied hydrogel
contact lens materials are available containing 30% to 80 % by weight of water and are based on
lightly crosslinked (0.5-1.0)% combination of various monomer including, for example, 2-
hydroxyethyl methacrylate (HEMA), acrylamide (AAm), acrylic acid (AA),ethylene glycol
dimethacrylate (EGDMA), Poly vinyl alcohols (PVA), chitosan (Cs), ethylhexyl methacrylate
(EHMA), poly vinyl pyrrolidone (PVP), Methylacrylate (MA) and Methyl cellulose (MC). Of all
poly (HEMA) cross-linked with EGDMA is the basis of many types of soft contact lenses [Pedley

©ARC Page | 1
Dr. Mohammed A. Muter

et al. 1980]. A useful property of hydrogel contact lenses is water imbibition of hydrogels because
the greater the amount of water content of a lens, the greater the amount of dissolved oxygen in
the lens and, in turn, the greater the amount of atmospheric oxygen that can reach the cornea
[Refojoet al.1991]. Water imbibition is the ability of the contact lens to absorb water and swell. It
is a property that depends on the ratio of hydrophilic to hydrophobic functional groups on the
polymer and on the nature of these groups as well [Refojo.1991].It is one of the most
contaminants that is most frequently occurring on contact lenses, and it results from the
interaction between the tear film and polymer of a contact lens[Michaudet al. 1998;Merindano et
al.1998].Yet the hydrogels used in soft contact lenses and containing AA adsorbs considerably
more protein than other gels [Holly1984 ;Sack et al.1987].The hydrogel spoilage from tear film is
one of the major problems with hydrophilic contact lenses. Such spoilage of contact lenses is
because of the different factor such as calcium films, organic plaques and protein films [Bohnertet
al.1988]. The important thing for the wearers of contact lenses and for practitioners is
transmittance properties of theses contact lenses. And this is not only for ultraviolet radiation
(UVR) protective properties, but also for visual performance [Garrettet al.1999; Gallagher et al.
2006].
The present study includes polymerization of 2-HEMA and 2-EHMA by free radical
polymerization to produce hydrogel contact lenses and study swelling measured, protein
adsorption, oxygen permeability and transmittance for these hydrogel lenses.
2. EXPERIMENTAL
2.1. The Materials
Hydroxylethyl methacrylate (MERCK), Methylacrylate (ALDRICH), Chitosan (ACROS),
Ethylhexyl methacrylate (MERCK), acrylic acid (MERCK), Sodium hydroxide (BDH), Acetic
acid(BDH), Phosphate buffered saline (HIMEDA), Benzoyl peroxide (HIMEDA), Ethylene
glycol dimethacrylate (MERCK), Bovine serum albumin (HIMEDA), Sodium dodecyl Sulfate
(HIMEDA) and 1,6 hexandioldiacrylate (ALDRICH).
2.2. Apparatus
(Oven)Trivp International Crop. Italy, (FTIR 8400S) Fourier Transform infrared
spectrophotometer,Shimadzu,Jaban,(UV-1800PC),Ultraviolet-visiblespectrophotometer,
Shimadaz, Italy, was used to measure transmittance of hydrogel contact lenses.(UV-1650 PC)
Ultra violet-visible spectrophotometer, Shimadaz, Jaban, was used to the measure of protein
adsorption.(Hotplate stir)[Link](PH meter)Hanna, Romania.
2.3. Polymerization (HEMA)-Based Hydrogels
A (0.015) mole of HEMA with different moles of EGDMA (0.0025, 0.0037, 0.005, 0.006, 0.007)
as a crosslinking agent have been polymerized. The polymerization was initiated by using 0.0012
mole benzoyl peroxide dissolved in 5 ml DMF was used an initiator. The mixture was refluxing
for 6hrs at 80°[Link] gas was bubbled throughout solutions about 6hrs. When polymerization
has been completed, the hydrogel was removed carefully, and then the hydrogel was dried under
vacuum at (37°C) for overnight. The dry hydrogel of each was weighed [Ferreira et al. 2006].
2.4. Copolymerization
2.4.1. Copolymerization of (HEMA-co-AAm)
HEMA with AAm by using three different percentage molar ratios (10%,30%,50%).When mixed
AAm with HEMA,1ml of N,N,N´,N´-tetramethlene ethylene diamine (TEMED) was added as an
accelerator. Then added 0.0025 moles (EGDMA) as crosslinking agent and 0.0012 moles of BPO
dissolved in 5 ml DMF was used an initiator. The mixture was refluxing for 6 hrs at 80°C,
nitrogen gas was bubbled throughout the solutions for 6 hrs. When polymerization has been
complete, the hydrogels was removed carefully, then the hydrogels were dried in a vacuum oven
at (37°C) for overnight. The dry hydrogel of each was weighed [Sadeghi 2010].
2.4.2. Copolymerization of (HEMA-co-AA)
The copolymer was synthesized from the reaction of HEMA with AA by using three different
percentage molar ratios (10%, 30%, 50%).AA was prepared by naturalization sodium hydroxide

International Journal of Research Studies in Biosciences (IJRSB) Page | 2

Synthesis and Biocompatibility of New Contact Lenses Based On Derivatives of 2-Hydroxy Ethyl
Meth Acrylate and 2-Ethyl Hexyl Methacrylate

before use. Then the solutions were added to HEMA monomer. Then added 0.001 moles1,6-
Hexanediol diacrylate (HDODA) as crosslinking agent and 0.0012moles of BPO dissolved in 5
ml DMF was used an initiator. The mixture was refluxing for 6 hours at 80°C, nitrogen gas was
bubbled throughout the solutions for 6 hrs. When polymerization has been complete, the
hydrogels were removed carefully, then the hydrogels was dried in a vacuum oven at (37°C) for
overnight. The dry hydrogel of each was weighed. [Renjha et al .2013]
2.5. Terpolymerization with HEMA
The terpolymer was synthesized from reaction of HEMA with the monomers (Cs, MC, EHMA,
PVA), using three different percentage molar ratios(40%,40%,20%).Cs or MC was dissolved in
acetic acid solution as shown in Table [Link] the other hand (10)gm of PVA was dissolved in 90 ml
distillate water. The solution was refluxed at 90°C for 6 hours and kept at room temperature for
24 hours before using. When mixed (Cs, MC, EHMA, PVA), with HEMA, 0.0025 moles
(EGDMA) were added as crosslinking agent and 0.0012 moles of BPO dissolved in 5 ml DMF
was used an initiator. The mixture was refluxing for 6 hrs at 80°C, nitrogen gas was bubbled
throughout the solutions for 6 hrs. When polymerization has been complete, the hydrogels was
removed carefully, then the hydrogels was dried in a vacuum oven at (37°C) for overnight. The
dry hydrogel of each was weighed Standard formulations for the 3 hydrogels used in this study
are listed in Table 2[Bengani et al.2012].
Table1. Percentage of Cs, MC in acetic acid
Cs, MC % Wight (gm) Vml acetic acid 0.1 (moles)
10% 0.2 15
30% 0.6 30
50% 1 50
Table2. Different terpolymer used in this study
Material Percentage weight% Crosslinking 0.0025 (moles)
HEMA 40 40 40 40 EGDMA
EHMA 20 - - - EGDMA
MC 40 - - - EGDMA
PVA - 20 - - EGDMA
Cs - 40 - - EGDMA

2.6. Polymerization of (EHMA) Based Hydrogel

A(0.01) moles EHMA with a different concentrations of HDODA (0.001,0.002,
0.003,0.004,0.005) moles as acrosslinking agent was polymerized. The polymerization begins
when using (0.0012) moles of benzoyl peroxide was used an initiator. The mixture was refluxing
for 6 hrs at 80°C, nitrogen gas bubbled throughout the solutions for 6 hours. When polymerization
has been complete, the hydrogel was removed carefully, then the hydrogels was dried in a
vacuum oven at (37°C) for overnight. The dry hydrogel of each was weighed [Bengani et
al.2012].
2.7. Terpolymerization of EHMA
The terpolymer was synthesized from reaction of EHMA with the monomers PVP and MA by
using three different percentage molar ratios (40%,40%,20%) as shown in Table [Link] mixing
EHMA with PVP and MA, 0.001 moles (HDODA) were added as crosslinking agent and 0.0012
moles of BPO dissolved in 5 ml DMF was used an initiator. The mixture was refluxing for 6 hrs
at 80°C, nitrogen was bubbled throughout the solutions for 6 hrs. When polymerization has been
complete, the hydrogels was removed carefully, then the hydrogels was dried in vacuum oven at
37°C for overnight. The dry hydrogel of each was weighed [Bengani et al.2012].
Table3. Terpolymer used EHMA in this study
Material EHMA MA PVP Crosslinking 0.01( mole)
% 40 20 40 HDODA

International Journal of Research Studies in Biosciences (IJRSB) Page | 3

Dr. Mohammed A. Muter

2.8. Swelling Measurement

The equilibrium water content in the distillate water was determined by the ratio of the weight of
water in the hydrogel to the total weight of the hydrogel at hydration equilibrium. EWC was
calculated by using the following equation.
Ws-Wd
EWC = x100
Ws
Where Ws and Wdcorrespondto the weight of the swollen sample and dried sample, respectively
[Jones 2005].
2.9. Oxygen Permeability
The relationship between EWC and oxygen permeability has been found to be (Morgan &Efron
equation):
Dk=1.67e 0.0397EWC
Where ‘EWC’ is the Equilibrium water content of the material. The units of Dkare known as
Barrer: [Morgan 1998]
2.10. Protein Adsorption
The hydrogel membranes were immersed in phosphate buffer solution (PBS, pH 7.4) 5ml for 24
hrs. After this step soaking the hydrogel membranes in a single protein solution of Bovine serum
albumin for 3 hrs at 34 °C the typical surface temperature of the human eye, the concentration of
protein solution was 0.5mg/ml. After adsorption the hydrogel membranes were placed gently in to
PBS for 5 second to remove excess solution adhering to the hydrogel membranes. The
membranes were then inserted into a glass tube containing 1wt% aqueous solution of sodium
dodecyl sulfate (SDS) to remove the proteins adsorbed on the membranes. The amount of proteins
adsorbed on the membrane surface was calculated from the concentration of proteins in the SDS
solution using the Bradford assay reagent kit [Higuchiaet al .2003].
2.11. Transparency Measurement
The transparency of the membrane was examined using UV-visible spectrophotometer, the
sample was prepared by solvent evaporation method and immersed in distill water for 24 hours to
reach swelling equilibrium. The measurement was performed from 200 to 700 (nm) wavelength at
room temperature [Li et al.2011].
3. RESULTS& DISCUSSION
3.1. Synthesis and Characterization
3.1.1. Synthesis and Characterization of Hydrogel (HEMA-co-AA)
CH3 O O
HDODA / BPO /DMF
H
CH2 C C O CH2
2
OH + CH2 C C O H
80° C /6 h /N2
HEMA AA

CH3
H2
C C CH2 CH CH2 CH C
H2
C O
C O C O
O
O
OH
CH2

CH2 (CH2)6

OH O
CH3 C O
C C H2C C CH2 CH C
H2 H H2
C O
C O
O
OH
CH2

CH2

OH

Scheme (3-1) Copolymerization and Crosslinking with EGDMA of (HEMA-co-AA)

International Journal of Research Studies in Biosciences (IJRSB) Page | 4
Synthesis and Biocompatibility of New Contact Lenses Based On Derivatives of 2-Hydroxy Ethyl
Meth Acrylate and 2-Ethyl Hexyl Methacrylate

The (HEMA-co-AA) was synthesized from the reaction of (HEMA) with (AA) by using different
percentage ratios (10%, 30%, 50%) in presence of HDODA as acrosslinking agent and BPO as an
initiator by refluxing it with DMF as solvent for 6 hours. The mixture was gently stirred while
nitrogen purged through the mixture to remove any dissolved oxygen. This reaction was shown in
Scheme 1.
FTIR Spectrum
The FTIR Spectrum of (HEMA-co-AA),is shown in Figure 1 ,which indicates the absorption band
at 3433cm-1 to (-OH str group), 3402cm-1 to(COOH str group)2938cm-1,2829cm-1 to(C-Hstr
aliphatic polymer backbone), 1750cm-1 (C=O str ester group),1149cm-1 to (C-O-C str) and 1082
cm-1to(-C-O of C-OH str)[Silverstien et al.2011 ; Pretsch et al .2009; Pavia et al.2009;Rao.1963 ].
3.2. Synthesis and Characterization of Hydrogel (HEMA-co-AAm)
The (HEMA-co-AAm) was synthesized from the reaction of (HEMA) with (AAm) by using
different percentage ratios (10%,30%,50%) in the presence of EGDMA as a crosslinking agent,
BPO as aninitiator,and1ml of TEMED was added as accelerator by refluxing it with DMF as
solvent for 6 hrs. The mixture was gently stirred while nitrogen was purged through the mixture
to remove any dissolved oxygen. This reaction was shown in Scheme 2.
CH 3 O O
EGDMA / BPO /DMF
CH2 C C O CH2 OH + CH2 C C NH2
2 H 80 °C /6 h /N2/TEMED

CH3 CH3
H2 H2 H
C C CH2 C C C C
H2
C O
C O C O
O
O
CH2 CH2 NH2

CH2 CH2

OH O
C O
CH3
C C H2C C CH2 CH C
H2 H2
C O
CH3 C O
O
H2N
CH2

CH2

OH

Scheme (3-2) Copolymerization and Crosslinking with EGDMA of (HEMA-co-AAm)

FTIR Spectrum
FTIR Spectrum of (HEMA-co-AAm),is shown in Figure 2 ,which indicates the absorption band
at; 3355cm-1 to (-OH str group), 3311cm-1 to (N-H str group), 2947cm-1, 2885cm-1 to (C-H str
group of polymer backbone),1720cm-1 to (ester group, C=O str group), 1674 cm-1 to (N-H-
C=O)1380cm-1 to (C-N), 1157 cm-1 to (C-O-C str group) and 1080 cm-1 to (-C-O of C-OH
str)[Silverstien et al.2011 ; Pretsch et al .2009; Pavia et al.2009; Rao.1963].
3.3. Synthesis and Characterization of Hydrogel (HEMA-co-MC-co- EHMA)
O
CH3 O
O O
CH2 C C O CH2 OH + + O
2 O
O O n

HEMA O
MC EHMA
EGDMA / BPO /DMF

80 °C /6 h /N2

CH3 H3C CH3

H H
MCO C H2C C H2C C H2 C CH C OCM
CMe C O C O C O CMe m
C O O O O C O
O CH2 CH2 CH2 O
H2C H2C H2C
O OH OH OH O
C O C O
CH2 CH
CH CH2
n
CH3 CH3
H2
MCO CH C C CH2 C CH2 CH OCM
C O C O

O O

.
Scheme (3-3) Copolymerization and Crosslinking with EGDMA of (HEMA-co-MC-co-EHMA)

International Journal of Research Studies in Biosciences (IJRSB) Page | 5

Dr. Mohammed A. Muter

The (HEMA-co-MC-co-EHMA) was synthesized from the reaction of HEMA with MC and
EHMA in the presence of EGDMA as a crosslinking agent and BPO as an initiator by refluxing it
with DMF as solvent for 6 hours. The mixture was gently stirred nitrogen was purged through the
mixture to remove any dissolved oxygen. This reaction was shown in Scheme 3.
FTIR Spectrum
The FTIR Spectrum of (HEMA-co-MC-co-EHMA), is shown in Figure 3 ,which indicated
absorption band; The peak in the range of 3440 cm-1is very broad to hydroxyl group (-OH str),
2923cm-1 ,2854cm-1 to (C-H str of polymer backbone ),1728 cm-1 to (ester group, C=O
str),1149cm-1 ,1072 cm-1 to (C-O-C str) and 1026 cm-1 to (-C-O of C-OH str).[Silverstien et
al.2011 ; Pretsch et al .2009; Pavia et al.2009; Rao.1963]
3.4. Synthesis and Characterization of Hydrogel (HEMA-co-Cs-co-PVA)
The (HEMA-co-Cs-co-PVA) was synthesized from the reaction of (HEMA) with(Cs) and PVA
by using different percentage ratios(10%,30%,50%) in the presence of EGDMA as a crosslinking
agent and BPO as an initiator by refluxing it with DMF as solvent for 6 hours. The mixture was
gently stirred while nitrogen purged through the mixture to remove any dissolved oxygen. This
reaction was shown in Scheme 4.
CH3 O
OH
CH2 C C O CH2 OH
2
OH + O
+ CH2 CH
NH O
HO n
HEMA C O
HO OH
CH3 x
NH2 PVA
Chitosan

EGDMA / BPO /DMF

80 ° C /6 h /N2

CH3 CH3 CH3

H2
C C H2C C CH2 C C
H2
C O C O
O
O
m
O=C
HO HO
CH3
O
O C
NH2 OH
NH OH CH2
O 2
O
HO
HO x O
CH 3 C O

C C CH2 C CH2 CH
H2
CH3
C O n
O
HO

HO

NH2 OH CH 3
O C
OH
O NH

HO
HO x

Scheme (3-4) Copolymerization and Crosslinking with EGDMA of (HEMA–co-Cs-co-PVA)

FTIR Spectrum
The FTIR Spectrum of (HEMA-co-Cs-co-PVA), is shown in Figure 4 ,which indicated absorption
band at 3379cm-1 to (-OH str group), 3352cm-1 to (N-H str), 2931cm-1 ,2885 cm-1 to (C-H str of
polymer backbone),1720 cm-1 to (ester group, C=O str), 1658cm-1 to (N-H-C=O), 1072 cm-1 to
(C-O-C str) ,1018 cm-1to (-C-O of C-OH str) and 1157cm-1 to (C-N str)[Silverstien et al.2011 ;
Pretsch et al .2009; Pavia et al.2009; Rao.1963].
3.5. Synthesis and Characterization of Hydrogel (EHMA-co-PVP-co-MA)
The (EHMA-co-PVP-co-MA) was synthesized from the reaction of (EHMA) with (PVP) and MA
in the presence of HDODA as a crosslinking agent and BPO as aninitiator by refluxing it with
DMF as solvent for 6 hours. The mixture was gently stirred while nitrogen purged through the
mixture to remove any dissolved oxygen. This reaction was shown in Scheme 5.
FTIR Spectrum
The FTIR Spectrum of (EHMA-co-PVP-co-MA),is shown in Figure 5 ,which indicates the
absorption band; 2947cm-1,2862cm-1to (C-H str of polymer backbone),1735 cm-1 to (ester group,
C=O str),the absorption band 1450cm-1,1388 cm-1 were assigned to the characteristic vibration of
International Journal of Research Studies in Biosciences (IJRSB) Page | 6
Synthesis and Biocompatibility of New Contact Lenses Based On Derivatives of 2-Hydroxy Ethyl
Meth Acrylate and 2-Ethyl Hexyl Methacrylate

the pyrrolidone ring, 1164 cm-1 to (C-O-C str) and 1064 cm-1 to (-C-O of C-OH str)[Silverstien et
al.2011 ; Pretsch et al .2009; Pavia et al.2009; Rao.1963].
3.6. Water Content
3.6.1. Effect of Acrylic acid on Water Content of Hydrogel HEMA
In order to increase the water content and the oxygen permeability of contact lenses the polar
monomer, acrylic acid (AA) and 2-hydroxyethyl methacrylate (HEMA) are polymerized into
hydrogels. Hydrogels (AA-co-HEMA) have been extensively studied in the biomedical and
pharmaceutical fields for a variety of applications including soft contact lenses. The EWC is the
most significant single property of the gel since it is the water held within the polymer substrate
that gives hydrogels their unique properties. When added AA to a soft lens polymer formulation,
it results in a soft lens with ionized groups (negatively charged) within the polymer matrix,
allowing the lens to absorb more water. The conversion of the carboxyl group (CO2H) to the more
hydrophilic ionized form (the carboxyl ate anion, CO2-) produces an increase in water
content[Castillo et al.1986].This is commonly achieved by treating AA with sodium hydroxide,
the carboxylic acid groups are neutralized, as illustrated in the following equation:
R-CO2H + NaOH→ R-CO2Na + H2O
Figure 6: Equilibrium Water Content (EWC) for Different Ratios of AA (10%, 30% ,50%) :
3.6.2. Effect of Acrylamide on the Water Content of Hydrogel HEMA
The use of Acryl amide as a co-polymer with 2-HEMA in order to increase the water content of
hydrogels contact lenses which provide hydrogen bonding with water molecules in the site of
amine groups[Thakur et al.2011]Figure 7: Equilibrium Water Content (EWC) for Different Ratios
of AAm (10%,30% ,50%).
3.6.3. Effect of Terpolymer on Water Content
Chitosan, poly vinyl alcohols and Methyl cellulose, are hydrophilic polymers and used in many
biomedical applications such as contact lenses because of non toxic and higher water content,
which contain many hydroxyl groups in both polymers that make hydrogen bonding with water
molecules,so increase the water content of hydrogels 2-HEMA,on other hand ethylhexyl
methacrylate and methylacrylate are hydrophobic monomers which reduce the water content
because of content methyl groups which decrease the water content of hydrogels contact
lenses[Moradi et al.2003]. Figure 8: Equilibrium Water content (EWC) for different ratios of
Terpolymer (HEME-co-PVA-co-Cs),(HEMA-co-EHMA-co-MC)and(EHMA-co-PVP-MA)
3.7. Protein Adsorption
During contact lens wear, tear film components such as lipids, mucines and proteins tend to
deposit on and within the lens material and may cause discomfort, reduced vision and
inflammatory reactions, The concentration of albumin in the tear film is relatively low compared
to the concentration in blood serum, but this value increases markedly under various conditions,
including when the eye is closed, during contact lens wear and in various dry eye states [Tigheet
al.2006].
Synthesized contact lens materials with various concentrations of relatively hydrophobic (MA,
EHMA) and hydrophilic (HEMA, AA, Cs, MC, PVA, AAm) components reported that increasing
levels of hydrophilic components decreased albumin deposition. Concentrations on hydrophobic
surfaces, as compared to relatively hydrophilic surfaces discern electrostatic attraction has a
strong impact on albumin deposition. The negatively charged albumin is more likely to deposit on
neutral or positively charged substrates than on materials with a net negative charge.Figure9 show
the effect of albumin deposition of lens material. Where 1-(HEMA-co-AA), 2-(EHMA-co-AAm),
3-(HEMA-co-PVA-co-Cs), 4-(HEMA-co-EHMA-co-MC), 5-(EHMA –co-PVP –co-MA)
3.8. Transmittance Measurement
The synthesized polymer must be transparent in order to be suitable for contact lenses. The UVR
spectrum is subdivided into three bands: UVC (100–280 (nm), UVB (280–315 (nm) and UVA
(315–400 (nm).The results show that all contact lenses tested allowed relatively uniform range of
International Journal of Research Studies in Biosciences (IJRSB) Page | 7
Dr. Mohammed A. Muter

transmittance of approximately 57-95.6% , at wavelengths between 400-700(nm) and below 240

(nm)will be less than 1% transmittance for all contact lenses[Bergmanson [Link].1997]. The
percentages of light transmission at 290(nm) for terpolymer (HEMA-co-MC-co-EHMA),(
HEMA-co-PVA-co-Cs) and (EHMA-co-MA-co-PVP) are (13.8,11.7 and 27.2)% respectively a
higher than copolymer (HEMA-co-AA) and (HEMA-co-AAm) are (6.1,8.3)% respectively. The
percentage of light transmission at 400 (nm) for terpolymer (HEMA-co-MC-co-EHMA),(HEMA-
co-PVA-co-Cs) and (EHMA-co-MA-co-PVP) give higher light transmittance(73, 82.3 and
94.2)%than copolymer give the light transmittance lower than terpolymer (HEMA-co-AA),
(HEMA-co-AAm) (57,69)%respectively.Figure10: Transmittance of Copolymer and Terpolymer
in the visible light wave range of 400-700 (nm).
3.9. Oxygen Permeability
The Oxygen permeability increase logarithmically with increase water content. It is essentially
governed by EWC in conventional hydrogels. This occurs since oxygen is able to pass through the
water rather than through the material itself. The relationship between EWC and oxygen
permeability has been found to be (Morgan &Efron equation)[Morgan [Link].1998]. Dk=1.67e
0.0397EWC
.Figure 11: Show Oxygen Permeability of Lens Material.Where1-(HEMA-co-AA),2-(
HEMA-co-AAm), 3-(HEMA-co-Cs-co-PVA), 4-(HEMA-co-MC-co-EHMA), 5-(EHMA-co-MA-
co-PVP)
4. CONCLUSION
The results show the equilibrium water content increases with increasing hydrophilic groups in
hydrogels contact lenses. The oxygen permeability (Dk) increases logarithmically with increasing
water content of hydrogel contact lenses which increases permeability of oxygen and carbon
dioxide to promote normal corneal metabolism. Protein adsorption of hydrogel contact lenses
shows that albumin deposits in higher concentrations on hydrophobic surfaces as compared to
relatively hydrophilic surfaces. The transmittance of light (%T) was studied by UV
Spectrophotometer, the transmittance of hydrogels contact lenses shows that all hydrogel contact
lenses exhibited light transparency in the range 57-94.6 %.
ACKNOWLEDGMENTS
The authors gratefully acknowledge partial support of this work of Chemistry University of
Qadisiyah.
REFERENCES
Bergmanson J.P. and Sheldon T.M. (1997).Ultraviolet radiation revisited. CLAOJ.23,196-204.
Bengani C.L., Leclerc J., and Chauhan A.; 2012. Lysozyme transport in PHEMA hydrogel
contact lenses ,Journal of Colloid and Interface Science ,386:441-450
Bohnert J.L., Horbett T.A., Ratner B.D., Royce F.H. ;1988 .Adsorption of proteins from artificial
tear solutions to contact lens materials. Invest Ophthalmol Vis Sci; 29:362–373.
Castillo E.J., Koenig J.L., and Anderson J.M.; 1986. Protein adsorption on hydrogels,
Biomaterials, 6, 338-345.
Ferreira p., Calvinho p.,Cabrita S.A., Schacht E., and Gil H.M.; 2006. Synthesis and
characterization of new methacrylate based hydrogels, Brazilian Journal of
PharmaceuticalSciences, 42(3):239-2274
Gallagher R.P., and Lee, T.K. ; 2006 .Adverse effects of ultraviolet radiation: a brief Review.
ProgBiophysMolBiol; 92:119–31.
Garrett Q., Garrett R.W, MilthorpeB.K; 1999 .Lysozyme sorption in hydrogel contact lenses.
Invest Ophthalmol Vis Sci.; 40:897–903.
Higuchia A.,Sugiyamaa K.,Yoona B., Sakuraib M., Haraa M,.Sumitac M.,Sugawarac S., and
Shirai T .; 2003. Serum protein adsorption and platelet adhesion on pluronict-adsorbed
polysulfone membranes, Biomaterials, 24: 3235–3245
Holly F.J. [Link] aspects of contact lens biocompatibility. Colloids Surface; 10:343–350.
Jones L.; 2005. Contact lenses fitting today: Silicone hydrogel part 1: Technological
developments, continuing Education and Training, 23-28.
International Journal of Research Studies in Biosciences (IJRSB) Page | 8
 Synthesis and Biocompatibility of New Contact Lenses Based On Derivatives of 2-Hydroxy Ethyl
Meth Acrylate and 2-Ethyl Hexyl Methacrylate

Li L., Wang H.J., and Xin Z.; 2011 .Synthesis and biocompatibility of novel Silicon hydrogel
containing phosphorylcholine , European polymer Journal,47:1795-1803.
Merindano, M.D., Canals,M., Saona C., Potau J and Costa J. ;1998 .Observation of deposits on
disposable contact lenses by bio-light and scanning electron microscopy. Cont Lens Anterior
Eye; 21:9-55.
Michaud,L., and Giasson,C. (1998) .Comparing the extent of protein build-up on several
disposable lenses by two spectrophotometric methods, Cont Lens Anterior Eye; 21: 8-104.
Moradi O., Modarress H., and Norouzi M.; 2003 .The Effects of Concentration, pH, and Ionic
Strength on Lysozyme Adsorption onto AA and HEMA Contact Lenses, Iranian Polymer
Journal ,12(6):477-484.
Morgan P.B., EfronN ; 2002 Trends in UK contact lens prescribing 2002. Optician. J, 223(5849),
28–30
Morgan P.B, and EfronN.; [Link] oxygen performance of contemporary hydrogel contact
lenses. Contact Lens and Anterior Eye; 21(1): 3-6.
Pavia L.D., Lampman L.G.,KrisS.G., and Vyvyan R.J.; 2009. Introduction to Spectrophotometer
4 [Link] general learning.
Pedley D.G., Skelly P.J., Tighe B.J.; 1980 Hydrogels in biomedical applications. Br PolymerJ,
12:99 –110.
Pretsch E., Buhlmann P., and Baderscher M.; 2009. Structure determine of Organic compound
4thed .springer-Verlag Berlin Heidelberg.
RaoC.M.R.; 1963 . Chemical application of infrared spectroscopy. academic press, New York.
RefojoM.F.; 1991. Water imbibition. In: Dabezies OH, editor. Contact Lenses: The CLAO Guide
to Basic Science and Clinical [Link] York: Grune and Stratton, 9:1–4.
Renjha M.N. and Khan S.; 2013. Chitosan/(poly vinyl alcohol) Based Hydrogels for Biomedical
Application ,Journal of pharmacy and Alternative Medicine ,2(1):30-40.
Sack R.A, Jones B., Antignani A., Libow R., Harvey H.; 1987. Specificity and biological activity
of the protein deposited on the hydrogel surface: relationship of polymer structure to biofilm
formations. Invest Ophthalmol Vis Sci; 28:842–849.
Sadeghi M.; 2010 .Synthesis and Swelling Behaviors of graft copolymer Based on Chitosan-g-
poly(AA-co-HEMA), International Journal of Chemical Engineering and Applications,
1:4:354-358
Silverstien R.M, Webster F.X and Kiemle D.J.; 2005. Spectrometric identification of Organic
compound 7thed . Joun Wiley and Sons.
Tighe B.; 2006 .Contact Lens Materials. In: Phillips A, Speedwell L, editors. Contact Lenses.
Edinburgh: Butterworth-Heinemann, pp 59 - 78.
Thakur A.,WanchooR.K.,and Singh P.; 2011. Hydrogels of Poly (acrylamide-co-acrylicacid): In-
vitro Study on Release of Gentamicin Sulfate, Chem. Biochem. Eng. Q. 25 (4): 471–482

International Journal of Research Studies in Biosciences (IJRSB) Page | 9

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