KR101863823B1 - Hydrogel contact lenses composition, including copolymerized hydrophilic terpolymers and silicones - Google Patents

Abstract

The present invention relates to a hydrogel contact lens composition comprising a copolymerized hydrophilic terpolymer and silicon, wherein hydrophilic acryl-based monomers are polymerized with monomers which can maintain mechanical strength, thereby enhancing light transmittance and oxygen permeability. For the purpose, the composition of the present invention comprises 30.0-60.0 wt% of N,N-dimethyl acrylamide, 7.5-10.0 wt% of copolymerized terpolymer, 5.5-10.0 wt% of N-vinylpyrrolidone, 5.0-10.0 wt% of 2-hydroxyethylmethacrylate, 2.0-5.0 wt% of ethylene glycol dimethacrylate, 10.0-15.0 wt% of glycerol monomethacrylate, and 10.0-20.0 wt% of a silicon monomer.

Description

Hydrogel contact lenses compositions comprising copolymerized hydrophilic terpolymers and silicones (Hydrogel contact lenses composition, including copolymerized hydrophilic terpolymers and silicones)

The present invention relates to a hydrogel contact lens composition comprising a copolymerized hydrophilic terpolymer and silicone capable of improving light transmittance and oxygen permeability through polymerization (polymerization) between hydrophilic acrylic monomers and monomers capable of maintaining mechanical strength .

In general, contact lenses are suitable for use with appropriate cornea, such as adequate tensile strength, bio compatibility, toxicity, optical transparency, refractive index, surface wettability, Water content, swelling, oxygen transmissibility, flexibility, and the like must be met.

Particularly, considering the problems and side effects of ophthalmic diseases caused by long-term wearing of contact lenses, the oxygen transmissibility requirement is very important.

Therefore, in order to improve the oxygen permeability of the contact lens, research and development of a material having excellent oxygen permeability has been actively carried out. An example of this is a prepolymer containing silicon.

Korean Patent No. 10-0901806 discloses a polyurethane resin composition for optical lens molding and an impact-resistant synthetic resin lens as a technology related to a lens manufactured by applying the above prepolymer.

The above-mentioned technique is a process for preparing a prepolymer obtained by reacting a substituted polyisocyanate having two or more isocyanate groups with a polyol having two or more hydroxyl groups, an internal mold release agent, and 4,4'-methylene bis (2-chloroaniline) As an essential ingredient.

However, such a lens made by applying such a prepolymer has a problem of wettability with a stain deposited product, and also has a problem that an oxygen permeability does not reach the corneal oxygen requirement rate, resulting in inconvenience to the user .

Korean Patent Laid-Open No. 10-2008-0059926 (Jul. 1, 2008) Korean Patent No. 10-1123644 (Feb. 28, 2012) Korean Patent No. 10-0346485 (July 16, 2002)

It is an object of the present invention to provide a hydrogel contact lens composition containing a copolymerized hydrophilic terpolymer and silicon having excellent oxygen permeability and light transmittance.

The composition of the present invention is characterized by comprising 30.0 to 60.0% by weight of N, N-dimethyl acrylamide, 7.5 to 10.0% by weight of a copolymerized terpolymer, N-vinylpyrrolidone (N 5.5 to 10.0% by weight of vinylpyrrolidone, 5.0 to 10.0% by weight of 2-hydroxyethylmethacrylate, 2.0 to 5.0% by weight of ethylene glycol dimethylacrylate, glycerol monomethacrylate 10.0 - 15.0% by weight of glycerol monomethacrylate, and 10.0 - 20.0% by weight of silicone monomers.

delete

Further, the silicone monomers may contain,

Of the present invention.

In addition, the terpolymer is a polymer composed of three kinds of monomers.

The hydrogel contact lens composition comprising the copolymerized hydrophilic terpolymer of the present invention having the above-described structure and silicone can be used for a long period of time because it has excellent light transmittance and oxygen permeability and can reduce the dryness and redness of the user's eyes. It is effective.

The hydrogel contact lens composition comprising the copolymerized hydrophilic terpolymer of the present invention and silicon,

30.0 to 60.0 wt% of N, N-dimethyl acrylamide, 7.5 to 10.0 wt% of copolymerized terpolymer, 5.5 to 10.0 wt% of N-vinylpyrrolidone, 5.0 to 10.0% by weight of 2-hydroxyethylmethacrylate, 2.0 to 5.0% by weight of ethylene glycol dimethylacrylate, 10.0 to 15.0% by weight of glycerol monomethacrylate, And 10.0 - 20.0% by weight of a silicone monomer. The copolymerization is carried out by reacting two or more raw materials, monomers or monomers of a polymer through a chemical reaction to produce a compound having a high molecular weight.

N, N-dimethyl acrylamide is a material prepared by hydrolyzing acrylonitrile (a decomposition reaction occurring due to the action of water molecules during chemical reaction), and when polymerized in water, (Polyacrylamide gel) can be synthesized in an arbitrary shape. In addition, it has a low adsorptivity and a good water-holding property, and is resistant to heat, alkali, and surfactant.

The N, N-dimethyl acrylamide may contain from 30.0 to 60.0% by weight of the total composition. When the N, N-dimethyl acrylamide is used in an amount of more than 60.0% by weight, column may not be easily separated, and when it is less than 30.0% by weight, denaturation may easily occur due to heat, acid alkali or the like.

The terpolymer is a polymer composed of three kinds of monomers and is contained in an amount ranging from 7.5% by weight to 10.0% by weight in the total composition so that mechanical strength with acrylic monomers can be maintained And the mixing of the hydrophilic monomers (acrylic) and the hydrophobic monomers (silicon) between the monomers is naturally carried out. When the amount of the terpolymer is more than 10.0% by weight, the mixing of the hydrophilic monomer and the hydrophobic monomer between the monomers as described above is unnatural. If the terpolymer is less than 7.5% by weight, the mechanical stiffness may be remarkably lowered.

The N-vinylpyrrolidone is usually called 'NVP' and has a substrate as a hydrophilic monomer. On the other hand, the N-vinylpyrrolidone may contain 5.5 to 10.0% by weight of the total composition. If it exceeds 10.0% by weight, the tensile strength and wettability of the contact lens are deteriorated If it is less than 5.5% by weight, the radical reaction by the thermal initiator of the monomers (reaction for generating a free radical) is not formed, and thus the substrate as a hydrophilic monomer can not be exerted.

2-hydroxyethylmethacrylate (2-hydroxyethylmethacrylate) is a hydrophilic acrylic monomer, which is a type of polymer having stereoregularity, and performs monomer-based crosslinking.

On the other hand, the 2-hydroxyethylmethacrylate may contain 5.0 wt.% To 10.0 wt.% Of the total composition. If it exceeds 10.0 wt.%, The molecules having stereoregularity The arrangement is irregularly tempered and light transmittance is markedly deteriorated. When it is less than 5.0% by weight, the copolymerization reaction becomes difficult.

The ethylene glycol dimethylacrylate serves as a crosslinking agent for synthesizing the respective components and may contain from 2.0 wt% to 5.0 wt% of the total composition. When the amount of ethylene glycol dimethylacrylate is more than 5.0% by weight, the synthesis of the polymer is excessive and hydrophobic monomers and functionalized hydrophilic monomers can be integrated. When the amount of ethylene glycol dimethylacrylate is less than 2.0% by weight, The content thereof is extremely small, making it difficult to synthesize or bond the components.

The glycerol monomethacrylate is a monomer-based crosslinked copolymer and may contain from 10.0% to 15.0% by weight of the total composition. When the glycerol monomethacrylate is more than 15.0% by weight, the polymer is excessively synthesized in the same manner as the ethylene glycol dimethylacrylate described above, and hydrophilic monomers and hydrophilic functionalized hydrophilic reactors Monomers can be integrated, and when the content is less than 10.0% by weight, the synthesis or the bonding between the respective components is difficult due to the insufficient content.

Meanwhile, in the present invention, the silicone monomer has a chemical structure formed as follows,

Monomer: 40 to 60% by weight of a polymer (mocromer): 40 to 60% by weight.

Hereinafter, the present invention will be described more specifically by way of Examples and Experimental Examples.

[Example 1]

(a) 10 g (0.086 mol) of a copolymerized terpolymer and 100 ml of ethylene glycol dimethylacrylate were placed in a 250 ml shrunk flask and the copolymerized terpolymer . Next, 30 mL of hydrogel type 2-hydroxyethylmethacrylate (HEMA) (b) was added dropwise to the shrunk flask under a low temperature and argon atmosphere using a funnel (DROP FUNNEL) (DROPWISE) and stirred for 24 hours.

When the reaction is carried out in a low temperature environment as described above, the reaction proceeds slowly, so that the yield of the product can be increased, and the reactivity of the product by reaction with hydrogen chloride (HCl) can be reduced.

Next, the solution obtained from the reaction was filtered using a filter to remove impurities and foreign substances, and the solution was lyophilized under reduced pressure to a concentration of about 10 ml. The concentrated solution was then polymer extracted with 400 ml of acetone. Thereafter, it was dried with a vacuum filter to obtain a polyphosphazene substituted with a vinyl group and 2-hydroxyethylmethacrylate.

Meanwhile, in order to examine the chemical structure of the polyphosphazene substituted with 2-hydroxyethylmethacrylate, ¹ H-NMR spectrum was measured using a Bruker AC-300 MHz spectrometer .

(a) polyphosphazene in which a copolymerized terpolymer is substituted with a vinyl group and (b) 2-hydroxyethyl methacrylate (HEMA), a vinyl group and 2-hydroxyethyl methacrylate The process for preparing a polyphosphazene is described in the following reaction scheme.

[Example 2]

The copolymer obtained in Example 1 and the polyphosphazene substituted with 2-hydroxyethylmethacrylate were cast by a cast mold, A hydrogel contact lens including a hydrophilic terpolymer and silicon was prepared.

(C) N-vinylpyrrolidone (NVP) and (d) ethylene glycol di (meth) acrylate were added to a polyphosphazene substituted with a vinyl group and 2-hydroxyethylmethacrylate. Ethylene glycol dimethylacrylate (EGDME) was added to the mold, and the mixture was maintained at 70 ° C for 40 minutes. Subsequently, the hydrogel contact lens was finally completed by heating at 80 DEG C for 40 minutes and then heat-treating at 100 DEG C for 40 minutes, that is, by copolymerizing.

(A) polyphosphazene substituted with a vinyl group, (b) 2-hydroxyethylmethacrylate (HEMA), (c) N-vinylpyrrolidone (NVP) Four hydrogel contact lenses P1, P2, P3 and P4 were prepared by varying the composition ratios of ethylene glycol dimethylacrylate (EGDMA) and (d) ethylene glycol dimethylacrylate (EGDMA) Respectively.

Polyphosphazene substituted with a vinyl group HEMA NVP EGDMA P1 1.96 wt% 92.65 wt% 4.90 wt% 0.49 wt% P2 4.76 wt% 90.00 wt% 4.76 wt% 0.48 wt% P3 6.54 wt% 88.32 wt% 4.67 wt% 0.47 wt% P4 9.09 wt% 85.91 wt% 4.55 wt% 0.45 wt%

[Experimental Example 1] Effect of the hydrogel contact lens according to the present invention

Water content, optical transmittance, and oxygen transmittance were measured to confirm the effect of the hydrogel contact lens of P1, P2, P3, and P4 of Example 2 above.

The hydrogels contact lenses of P1, P2, P3 and P4 of Example 2 were immersed in 0.9% sodium chloride (NaCl) physiological saline solution for 24 hours and then measured by the gravimetric method of ISO 18369-4 . The light transmittance (%) was measured using TM-2 of TOPCON in the visible light range (380 - 720 nm). The oxygen permeability (Dk / t) was measured with an O ₂ permeator 201T manufactured by Rdhder Development Company. On the other hand, in order to increase the accuracy of the measurement, the measurement was repeated three times each, and the average of the measured values is shown in Table 2 below.

Moisture content (%) Light transmittance (%) The oxygen permeability (Dk / t) P1 35.45 89 52 P2 32.21 89 79 P3 30.89 88 90 P4 28.00 89 101

Referring to Table 2, it can be seen that the hydrogel contact lens according to the present invention is excellent as a contact lens because it has an excellent oxygen transmission rate and a water content of about 30%. In addition, since the hydrogel contact lens according to the present invention has excellent light transmittance and oxygen transmittance, it is possible to reduce dryness and redness of eyes, and consequently it can be concluded that the lens is suitable for wearing for a long time.

Claims (4)

30.0 to 60.0 wt% of N, N-dimethyl acrylamide, 7.5 to 10.0 wt% of copolymerized terpolymer, 5.5 to 10.0 wt% of N-vinylpyrrolidone, 5.0 to 10.0% by weight of 2-hydroxyethylmethacrylate, 2.0 to 5.0% by weight of ethylene glycol dimethylacrylate, 10.0 to 15.0% by weight of glycerol monomethacrylate, , 10.0 - 20.0% by weight of a silicone monomer,
The silicone monomers may include,

Wherein the chemical structure of the hydrogel contact lens composition is a chemical structure of the hydrophilic polymer. delete delete The method according to claim 1,
Wherein the terpolymer is a polymer consisting of three kinds of monomers. The composition according to claim 1, wherein the terpolymer is a polymer comprising three kinds of monomers.