[논문]Compatibility of POSS Composites with Silicone Monomers and Application to Contact Lenses Material

Lee, Min-Jae; Lee, Kyungmun; Sung, A-Young

doi:10.5012/jkcs.2020.64.6.354

Compatibility of POSS Composites with Silicone Monomers and Application to Contact Lenses Material 원문보기

대한화학회지 = Journal of the Korean Chemical Society, v.64 no.6, 2020년, pp.354 - 359

Lee, Min-Jae (Department of Optometry & Vision Science, Daegu Catholic University) , Lee, Kyungmun (Devision of Research & Development, Vision Science Co., Ltd.) , Sung, A-Young (Department of Optometry & Vision Science, Daegu Catholic University)

Abstract ▼ AI-Helper

This research was conducted to analyze the compatibility of used monomers and produce the high functional contact lens material containing silicone monomers. Silicone monomer (Sil-OH), Trimethylsilylmethacrylate (TSMA) were used as additives for the basic combination of Polyhedral Oligomeric Silsesquioxane (POSS), methyl methacrylate (MMA) and methyl acrylate (MA). And also, the materials were copolymerized with ethylene glycol dimethacrylate (EGDMA) as the cross-linking agent, AIBN (thermal polymerization initiator) as the initiator. It is judged that the fabricated lenses of all combinations are optically excellent and thus used monomers have good compatibility. Measurement of the optical and physical characteristics of the manufactured hydrophilic lens material were varied in each case. Especially TSMA with POSS increases the oxygen permeability and Sil-OH with POSS increases the wettability by the addition of Sil-OH. These materials were considered to have compatibility each other, so it can be used in functional contact lens material.

주제어

표/그림 (12)

그림 Figure 1. Chemical structures of monomer. (a) POSS, (b) Sil-OH (n=49.20), (c) TSMA.
표 Table 1. Percent composition of samples (Unit: wt %)
$Figure 2. Comparison of the relation between refractive index and water content of samples.$ 그림 Figure 2. Comparison of the relation between refractive index and water content of samples.
표 Table 2. Optical transmittance distribution of samples
표 Table 3. Contact angle & water content of samples
그림 Figure 3. Comparison of the relation between DK and water con-tent of samples.
그림 Figure 4. Typical DSC thermogram analysis of sample. (a) PS50 heating state, (b) PS50 cooling state, (c) PT50 heating state, (d) PT50 cooling state.
$Figure 5. Comparison of the relation between refractive index and water content of samples.$ 그림 Figure 5. Comparison of the relation between refractive index and water content of samples.
그림 Figure 6. Contact angle of samples.
그림 Figure 7. Contact angle image of samples. (a) PS50, (b) PT50.
그림 Figure 8. Comparison of the relation between DK and water content of samples.
표 Table 4. Optical transmittance distribution of samples

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제안 방법

Based on POSS, silicone monomer (Sil-OH) and trimethylsilylmethacrylate (TSMA) were added as additives by ratio, and then polymerized through a thermal polymerization method. After measuring and evaluating the physical properties of the contact lens produced through the cast mold technique, the compatibility of POSS and the organic groups was evaluated to assess the usability of the lens material.
For the polymerization of a highly oxygen-permeable lens material, mixtures were prepared by adding POSS at a 1~10% ratio to the basic combination of DMA, MMA, MA, EGDMA, and AIBN, and the samples prepared as such were named P1, P3, P5, P7, and P10, respectively. To optimize the shape of the lens while maintaining its basic properties, the P10 sample, which had the best oxygen permeability, was selected, and Sil-OH and TSMA were added at a rate of 10, 30, 50, and 100%, respectively.
In the experiment in this study, POSS was intended to be grafted onto a highly oxygen-permeable hydrogel lens material by utilizing a material that has excellent gas permeability and improved mechanical properties. Based on POSS, silicone monomer (Sil-OH) and trimethylsilylmethacrylate (TSMA) were added as additives by ratio, and then polymerized through a thermal polymerization method.
The optical transmittance, refractive index, water content, wettability, oxygen permeability, eluate, and differential scanning calorimetry (DSC) of the produced polymers were measured to analyze the optical, physical, and thermal properties. The relationships between the refractive index and the water content, the contact angle and the water content, and the oxygen permeability and the water content were compared.
To optimize the shape of the lens while maintaining its basic properties, the P10 sample, which had the best oxygen permeability, was selected, and Sil-OH and TSMA were added at a rate of 10, 30, 50, and 100%, respectively. The prepared samples were then named PS10, PS30, PS50, PS100, PT10, PT30, PT50, and PT100, respectively.

대상 데이터

and synthesized Sil-OH were used, while for TSMA and N, N-dimethylacrylamide (DMA), TCI products were selected. For methyl methacrylate (MMA), methyl acrylate (MA), and azobisisobutyronitrile (AIBN), Junsei products were selected. For the crosslinking agent, ethylene glycol dimethacrylate (EGDMA), Sigma-Aldrich products were selected.
For methyl methacrylate (MMA), methyl acrylate (MA), and azobisisobutyronitrile (AIBN), Junsei products were selected. For the crosslinking agent, ethylene glycol dimethacrylate (EGDMA), Sigma-Aldrich products were selected. The molecular weight of Sil-OH was 2165 Mw and the viscosity was measured as 40.
For the hydrogel lens material that was used in the experiment, POSS from Hybrid Plastics Co. and synthesized Sil-OH were used, while for TSMA and N, N-dimethylacrylamide (DMA), TCI products were selected. For methyl methacrylate (MMA), methyl acrylate (MA), and azobisisobutyronitrile (AIBN), Junsei products were selected.
To optimize the shape of the lens while maintaining its basic properties, the P10 sample, which had the best oxygen permeability, was selected, and Sil-OH and TSMA were added at a rate of 10, 30, 50, and 100%, respectively. The prepared samples were then named PS10, PS30, PS50, PS100, PT10, PT30, PT50, and PT100, respectively. The stirring solution was mixed for 60 minutes after mixing according to the mixing ratio, and for polymer polymerization, each sample was heat-treated in an oven at 135℃ for 120 minutes.

이론/모형

The refractive indices of the prepared hydrophilic hydrogel lenses were measured based on ISO 18396-4:2006 using an ABBE refractometer (ATAGO DR-A1, Japan), and were measured five times per sample, respectively, and an average value was used. The water content was measured based on ISO 1869-4:2006 using the gravimetric method, and were measured five times per sample, respectively, and an average value was used. The weights of the dried and watercontaining samples were measured using an electronic balance (XS205 DualRange, METTLER TOLEDO) and were then calculated using the corresponding calculation formula.

성능/효과

09×10^-11 cm²/sec (mlO2/ml×mmHg) according to the TSMA addition ratio. Based on the experiment results of this study, it is thought that the gas permeability increased due to the characteristics of the silicone material, owing to the increased oxygen permeability regardless of the change in water content. The relationship between the oxygen permeability and the water content of each combination is shown in Fig.
The results of the thermal analysis of the polymer prepared in this study showed that silicone monomer lowered the glass transition temperature to increase the elasticity of the lens, and trimethylsilylmethacrylate showed a single peak, confirming that the polymerization was more stable. The additive that was used in this study showed good compatibility with the existing POSS, and was shown to maintain optical transparency. In addition, the wettability was maintained irrespective of the water content, and the oxygen permeability was also maintained or slightly increased.
Contact angle. The measurement of the contact angles of the prepared lenses showed that the contact angle decreased from PS10 102.74° to PS100 89.30° according to the Sil-OH addition ratio, and increased from PT10 75.46° to PT100 80.01° according to the TSMA addition ratio. In contrast to the results of the previous studies, where the wettability also tended to increase when the water content was high, ¹⁸ the results of this study are judged to indicate a change in wettability regardless of the water content depending on the surface properties of the silicone material.
index and water content. The measurement of the refractive indices of the manufactured lenses showed that the refractive index increased from P1 1.369 to P10 1.390 according to the POSS addition ratio, and that the water content decreased from P1 75.24% to P10 60.79%. It is thus judged that the water content decreases as the amount of POSS increases, and the refractive index increases due to the increase in the crosslink density between the molecules.
Refractive index and water content. The measurement of the refractive indices of the prepared lenses showed that the refractive index increased from PS10 1.397 to PS100 1.433 according to the Sil-OH addition ratio, and that the water content decreased from PS10 60.66% to PS100 42.35%. Conversely, the addition of TSMA decreased the refractive index of PT10 from 1.
Optical transmittance. The measurement of the spectral transmittance to determine the optical properties of the manufactured lenses showed that the PS group had 66.51-29.45% UV-B transmittance, 88.89-80.07% UV-A transmittance, and 92.57-89.75% visible light transmittance. Although there was no significant difference in percentage, the transmittance was slightly lower in the UV-B region, showing a 55.
Optical transmittance. The result of the spectral transmittance to determine the optical properties of the manufactured lenses showed that the UV-B was 74.68-76.78%, the UV-A was 89.51-90.57%, and the visible light transmittance was 92.61% regardless of the POSS content in all the groups. It is thus considered that the structure of POSS does not have a significant influence in both the ultraviolet and visible regions.
In addition, the cage-type structure makes it possible to make highly oxygen-permeable materials by increasing the gas permeability in the molecular structure. The results of the thermal analysis of the polymer prepared in this study showed that silicone monomer lowered the glass transition temperature to increase the elasticity of the lens, and trimethylsilylmethacrylate showed a single peak, confirming that the polymerization was more stable. The additive that was used in this study showed good compatibility with the existing POSS, and was shown to maintain optical transparency.
The results of this study showed that polyhedral oligomeric silsesquioxanes does not affect the optical transparency of the lens, and increases the refractive index and lowers the water content. In addition, the cage-type structure makes it possible to make highly oxygen-permeable materials by increasing the gas permeability in the molecular structure.

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