KR20240003019A - Silicone hydrogel contact lenses - Google Patents

Abstract

Provided is a silicone hydrogel contact lens comprising a polymer of a silicon-containing macromonomer and polyethylene glycol.

Description

Silicone hydrogel contact lenses{SILICONE HYDROGEL CONTACT LENSES}

The present invention relates to a composition for forming a silicone hydrogel contact lens and a silicone hydrogel contact lens manufactured using the same.

In the case of contact lenses, the market size is continuously growing because they are widely used for cosmetic purposes other than to correct vision. Therefore, various research and new technological developments are underway, and based on this, new contact lenses with optimal physical properties are being released.

The purpose of the present invention is to provide a silicone hydrogel contact lens that exhibits high oxygen permeability, high moisture content, and excellent durability.

The objects of the present invention are not limited to the objects mentioned above, and other objects and advantages of the present invention that are not mentioned can be understood by the following description and will be more clearly understood by the examples of the present invention. Additionally, it will be readily apparent that the objects and advantages of the present invention can be realized by the means and combinations thereof indicated in the patent claims.

In one embodiment of the present invention, a composition for forming a silicone hydrogel contact lens is provided including a silicon-containing macromer and polyethylene glycol.

In one embodiment of the present invention, a silicone hydrogel contact lens is provided comprising a polymer of a silicone-containing macromer and polyethylene glycol.

The silicon-containing macromonomer includes a siloxane chain and a urethane bond, and may have one or two acrylic functional groups.

The polyethylene glycol may have a weight average molecular weight of 200 to 6000 g/mol.

The polymer of the silicon-containing macromonomer may be a hydrophilic monomer, a silicon-containing monomer, or a copolymer of all of these.

The silicone hydrogel contact lens may have a water content in the range of 40% to 65% and an oxygen permeability (Dk) of 70 to 120.

The silicone hydrogel contact lens has a tensile strength of 4 kgf/mm ² to 8 kgf/mm ² , an elongation of 100% to 200%, a tensile modulus of elasticity of 0.3 kgf/mm ² to 1.0 kgf/mm ² , and oxygen The permeability is 70 Х 10 ^-11 (cm ² /s) [ml O ₂ /(ml·mmHg)] to 120 Х 10 ^-11 (cm ² /s) [ml O ₂ /(ml·mmHg)], and the water content is This may be 45% to 65%.

The composition for forming a silicone hydrogel contact lens includes: 10 to 40% by weight of the silicone-containing macromonomer; 1 to 20% by weight of the polyethylene glycol; 10 to 50% by weight of hydrophilic monomer; 10 to 20% by weight of silicone-containing monomer; and the remainder of additives including a crosslinking agent and an initiator.

The silicone hydrogel contact lens exhibits high oxygen permeability, high moisture content, and excellent durability.

In addition to the above-described effects, specific effects of the present invention are described below while explaining specific details for carrying out the invention.

Hereinafter, embodiments of the present invention will be described in detail so that those skilled in the art can easily implement the present invention. The present invention may be implemented in many different forms and is not limited to the embodiments described herein.

When a lens is inserted into the eye, it is placed on the cornea. Since the cornea has no blood vessels, it must receive oxygen from the air. At this time, if a lens that is not permeable to oxygen is worn on the eye, oxygen may not be delivered and disease may result.

In the case of contact lens materials, a polymerization reaction proceeds as a crosslinking reaction occurs due to instantaneous energy after a composition containing a plurality of monomers and an initiator is injected into the mold. At this time, the physical properties of the final product, contact lenses, are determined depending on how the composition is designed.

In one embodiment of the present invention, a silicone hydrogel contact lens comprising a polymer of a silicone-containing macromonomer and polyethylene glycol is provided.

When manufacturing existing hydrogel contact lenses, there is a limit to increasing oxygen permeability when the moisture content is high. In addition, it was confirmed that when the moisture content was increased, the Young's modulus decreased due to the characteristics of the hydrogel. In the case of Young's modulus, if the lens wearer is low, the lens wearer may feel comfortable, but a decrease in durability becomes a problem. In the case of durability, the degree can be measured by strength and elongation. Therefore, the high moisture content of the lens has been faced with the limitation that it may have a negative effect on oxygen permeability and durability.

The silicone hydrogel contact lens not only satisfies high oxygen permeability and high water content at the same time by using polyethylene glycol, but also exhibits excellent durability.

As used herein, “hydrogel” refers to a crosslinked polymer material that, when hydrated, can contain at least 10% by weight water within the matrix of the crosslinked polymer.

In this specification, “silicon-containing macromonomer” is a monomer that contains silicon and has an ethylenically unsaturated group, and has a weight average molecular weight of 500 Da or more.

In this specification, “polyethylene glycol” is represented by the formula H-(O-CH ₂ -CH ₂ ) _n -OH, and n generally has a value of 4 or more.

In this specification, “hydrophilic monomer” refers to a polymer of less than 500 Da having a polymerizable functional group of an olefin or acryl group and a hydrophilic functional group such as a hydroxyl group, an amine group, or pyrrolidone. It is a monomer.

In this specification, “silicon-containing monomer” is a monomer that contains silicon, has an ethylenically unsaturated group, and has a weight average molecular weight of less than 500 Da.

The silicone hydrogel contact lens may be manufactured by thermal polymerization or photopolymerization of a composition for forming a silicone hydrogel contact lens containing a silicone-containing macromonomer, a hydrophilic monomer, and polyethylene glycol.

Typically, silicone-containing polymers have high oxygen permeability. Accordingly, contact lenses using silicone materials have high oxygen permeability, but on the other hand, their water content is lowered due to their hydrophobic nature. If the content of hydrophilic monomer is increased in the polymer to increase the water content, the oxygen permeability decreases again. In this way, because the oxygen permeability and moisture content of contact lenses using existing silicone materials are in a complementary relationship (trade off), it is difficult to obtain a contact lens that satisfies the characteristics of high oxygen permeability and high moisture content at the same time.

The silicone hydrogel contact lens includes a polymer in which silicon-containing macromonomers are polymerized, and both oxygen permeability and moisture content satisfy predetermined standards or higher.

The polyethylene glycol is used as a processing aid during the polymerization of the silicone hydrogel contact lens, and plays roles such as dispersion, viscosity, and high hardness depending on the type of material forming the polymer, and also depending on the composition ratio of the composition. This can have a significant impact on the properties of the polymer formed. Since the terminal group of polyethylene glycol is a hydroxy group, it does not participate in the polymerization reaction and affects the formation of the structure by the gyration radius.

Accordingly, in the composition for forming the silicone hydrogel contact lens, the polyethylene glycol is involved in controlling the physical properties of the hydrogel, and as a result, the characteristics of high oxygen permeability and high moisture content of the silicone hydrogel contact lens can be achieved. make it possible

Since the silicone hydrogel contact lens is made of the silicon-containing macromonomer-based polymer, it has the characteristic of high oxygen permeability, and as described above, the polyethylene glycol acts as a processing aid to increase water content, thereby achieving high oxygen permeability. and high moisture content characteristics can be achieved.

In one embodiment, the silicon-containing macromonomer includes at least a plurality of siloxane repeating units [-Si-O-] and one or two acrylic functional groups.

In one embodiment, the silicone-containing macromer has a urethane bond.

In one embodiment, the weight average molecular weight of the silicon-containing macromer may be 500 Da to 2500 Da.

Specific examples of the silicon-containing macromonomer include methacryloxypropyltris(trimethylsiloxy)silane, monomethacryloxyalkyl terminated poly dimethylsiloxane, 3-{alpha-(trimethylsilyl)poly[oxy(dimethylisilylene) )]}Propyl 2-methylprop-2-enoate, mono-butyl terminated polydimethylsiloxane, methacrylooxypropyl terminated polydimethylsiloxane, mono vinyl terminated polydimethylsiloxane, bis(divinyl) terminated Terminated polydimethylsiloxane, alpha-monovinyl-monophenyl-Ω-monohydride terminated polymethylsiloxane, etc. are mentioned, but are not limited thereto, and may include one or more types thereof.

In one embodiment, the silicon-containing macromonomer is a compound represented by Formula 1, a compound represented by Formula 2, a compound represented by Formula 3, a compound represented by Formula 4, a compound represented by Formula 5, and combinations thereof. It may include at least one selected from the group consisting of.

<Formula 1>

In Formula 1,

x is an integer from 1 to 30, y is an integer from 5 to 30,

R ₁ is hydrogen or C1-C6 alkyl,

R ₂ to R ₅ are each independently C1-C8 alkyl, tri C1-C8 alkylsiloxy, phenyl, naphthyl, substituted C1-C8 alkyl, substituted phenyl, or substituted naphthyl, wherein alkyl The substituent is at least one selected from the group consisting of C1-C8 alkoxycarbonyl, C1-C8 alkyl, C1-C8 alkoxy, amide, trifluoromethyl, halogen, hydroxyl, carboxyl, C1-C8 alkylcarbonyl, and formyl. and the substituents of phenyl and naphthyl are at least selected from the group consisting of C1-C8 alkoxycarbonyl, C1-C8 alkyl, C1-C8 alkoxy, amide, halogen, hydroxyl, carboxyl, C1-C8 alkylcarbonyl, and formyl. It is one.

<Formula 2>

In Formula 2,

x and y are each independently an integer of 1 to 10, o is an integer of 1 to 60, p is an integer of 1 to 10, q is an integer of 1 to 10, and o, p and q The siloxane structural unit that can be repeated represents a random copolymer structure that can be connected in any order,

R ₁ to R ₂ are each independently hydrogen or C1-C6 alkyl,

R ₃ to R ₆ are each independently hydrogen, C1-C8 alkyl, tri C1-C8 alkylsiloxy, phenyl, naphthyl, substituted C1-C8 alkyl, substituted phenyl, or substituted naphthyl, wherein , the alkyl substituent is selected from the group consisting of C1-C8 alkoxycarbonyl, C1-C8 alkyl, C1-C8 alkoxy, amide, trifluoro methyl, halogen, hydroxyl, carboxyl, C1-C8 alkylcarbonyl and formyl. is at least one, and the substituents of phenyl and naphthyl are C1-C8 alkoxycarbonyl, C1-C8 alkyl, C1-C8 alkoxy, amide, halogen, hydroxyl, carboxyl, C1-C8 alkylcarbonyl, formyl and -(CH ₂ ) _z1 -(O-CH ₂ -CH ₂ ) _z2 (z1 is an integer from 1 to 4, and z2 is an integer from 3 to 12).

<Formula 3>

In Formula 3 above,

x is each independently an integer from 1 to 27, y is an integer from 3 to 27,

R ₁ and R ₂ are each independently hydrogen or C1-C8 alkyl,

R ₃ and R ₄ are each independently hydrogen, C1-C6 alkyl, tri C1-C6 alkylsiloxy, phenyl, naphthyl, substituted C1-C6 alkyl, substituted phenyl, or substituted naphthyl, where , the alkyl substituent is selected from the group consisting of C1-C6 alkoxycarbonyl, C1-C6 alkyl, C1-C6 alkoxy, amide, trifluoro methyl, halogen, hydroxyl, carboxyl, C1-C6 alkylcarbonyl and formyl. at least one, and the substituents of phenyl and naphthyl are selected from the group consisting of C1-C6 alkoxycarbonyl, C1-C6 alkyl, C1-C6 alkoxy, amide, halogen, hydroxyl, carboxyl, C1-C6 alkylcarbonyl and formyl. There is at least one selected.

<Formula 4>

In Formula 4 above,

x is each independently an integer from 1 to 27, y is an integer from 3 to 27,

R ₁ and R ₂ are each independently hydrogen or C1-C8 alkyl,

R ₃ and R ₄ are each independently hydrogen, C1-C6 alkyl, tri C1-C6 alkylsiloxy, phenyl, naphthyl, substituted C1-C6 alkyl, substituted phenyl, or substituted naphthyl, where , the alkyl substituent is selected from the group consisting of C1-C6 alkoxycarbonyl, C1-C6 alkyl, C1-C6 alkoxy, amide, trifluoro methyl, halogen, hydroxyl, carboxyl, C1-C6 alkylcarbonyl and formyl. at least one, and the substituents of phenyl and naphthyl are selected from the group consisting of C1-C6 alkoxycarbonyl, C1-C6 alkyl, C1-C6 alkoxy, amide, halogen, hydroxyl, carboxyl, C1-C6 alkylcarbonyl and formyl. There is at least one selected.

<Formula 5>

In Formula 5 above,

x is an integer from 1 to 8, y is an integer from 3 to 10,

R ₁ to R ₄ are each independently hydrogen or C1-C6 alkyl,

R ₅ is C1-C8 alkyl, tri C1-C8 alkylsiloxy, phenyl, naphthyl, substituted C1-C8 alkyl, substituted phenyl, or substituted naphthyl, wherein the substituent of alkyl is C1-C8 alkoxycarbohydrate. At least one selected from the group consisting of nyl, C1-C8 alkyl, C1-C8 alkoxy, amide, halogen, hydroxyl, carboxyl, C1-C8 alkylcarbonyl, and formyl, and the substituents of phenyl and naphthyl are C1-C8 alkoxy. It is at least one selected from the group consisting of carbonyl, C1-C8 alkyl, C1-C8 alkoxy, amide, halogen, hydroxyl, carboxyl, C1-C8 alkylcarbonyl, and formyl.

In one embodiment, the composition for forming a silicone hydrogel contact lens may include 10 to 40% by weight of the silicone-containing macromonomer.

In one embodiment, the polyethylene glycol may have a weight average molecular weight in the range of 200 to 6000 g/mol, and specifically, may have a weight average molecular weight in the range of 200 to 800 g/mol.

In one embodiment, the composition for forming a silicone hydrogel contact lens may include 1 to 20% by weight of polyethylene glycol as a processing aid.

In one embodiment, the silicone hydrogel contact lens may contain 1 to 20% by weight of polyethylene glycol.

The physical properties of the final product, a contact lens, are determined depending on how the composition of each component of the composition for forming the silicone hydrogel contact lens is designed. There may be many factors in the physical properties of contact lenses, but for example, they can be designed by mainly considering three factors: moisture content, oxygen permeability, and durability. Here, durability can be divided into strength, elongation, and Young's modulus. Considering the physical properties of such contact lenses, the composition for forming a silicone hydrogel contact lens may further include other components in addition to the silicone-containing macromonomer and the polyethylene glycol.

In one embodiment, the composition for forming a silicone hydrogel contact lens may further include a hydrophilic monomer, and the polymer of the silicone-containing macromer may be a copolymer of hydrophilic monomers.

The hydrophilic monomer participates in radical polymerization of the composition for forming the silicone hydrogel contact lens, and structural units based on the hydrophilic monomer are included in the polymer. The silicon-containing macromonomer and the hydrophilic monomer are polymerized through a radical reaction initiated by heat or light to form a polymer.

The hydrophilic monomers include, for example, N,N-dimethylacrylamide, 2-hydroxyethyl methacrylate, glycerol monomethacrylate, 2-hydroxyethyl methacrylamide, polyethylene glycol monomethacrylate, and methacrylate. It can be acid, acrylic acid, N-vinyl pyrrolidone, N-vinyl-N-methyl acetamide, N-vinyl-N-ethyl acetamide, N-vinyl-N-ethyl formamide, N-vinyl formamide, etc. It is not limited to this, and may include one or more types of these.

In one embodiment, the composition for forming a silicone hydrogel contact lens may include 10 to 50% by weight of the hydrophilic monomer. The composition for forming a silicone hydrogel contact lens can implement a contact lens having high water content characteristics while containing a hydrophilic monomer in a relatively low content of the above range compared to commercially available contact lenses.

In one embodiment, the composition for forming a silicone hydrogel contact lens may further include a silicone-containing monomer and a crosslinking agent. The polymer of the silicon-containing macromonomer may be a copolymer in which silicon-containing monomers are copolymerized.

The silicon-containing monomer is, for example, α,ω-bismethacryloxypropylpolydimethylsiloxane (SiGMA), 3-methacryloxypropyltris(trimethylsiloxy)silane (TRIS), monomethacryloxypropyl terminated poly It may be dimethylsiloxane, polydimethylsiloxane, 3-methacryloxypropylbis(trimethylsiloxy)methylsilane, methacryloxypropylpentamethyl disiloxane, etc., but is not limited thereto, and may include one or more types thereof.

In one embodiment, the composition for forming a silicone hydrogel contact lens may include 10 to 20% by weight of the silicone-containing monomer.

In one embodiment, the composition for forming a silicone hydrogel contact lens may further include a crosslinking agent.

The crosslinking agent is, for example, allyl methacrylate (AMA), divinylbenzene (DVB), triethylene glycol dimethacrylate (TrEGDMA), triallyl isocyanurate (TAIC), ethylene glycol dinethylacrylate. It may be EGDMA, ethylenediamine dimethacrylamide, glycerol dimethacrylate, etc., but is not limited thereto, and may include one or more types thereof.

In one embodiment, the composition for forming a silicone hydrogel contact lens may include 0.1 to 10% by weight of the crosslinking agent.

In one embodiment, the composition for forming a silicone hydrogel contact lens may further include an initiator. The initiator may be a thermal initiator or a photoinitiator that initiates a radical reaction by heat or light such as infrared or ultraviolet rays.

The initiator may be, for example, compounds such as lauryl peroxide, benzoyl peroxide, isopropyl percarbonate, azobisisobutyronitrile, etc., or aromatic alpha-hydroxy ketone, alkoxyoxybenzoin, acetophenone, tert-butyl It may include a photoinitiator such as peroxine adecanoate, acyl phosphine oxide, tertiary amine, diketone, or mixtures thereof. Examples of photoinitiators include 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methyl-1-phenyl-propan-1-one, bis(2,6-dimethoxybenzoyl)-2,4,4- Trimethylpentyl phosphine oxide (DMBAPO), bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide (Irgacure 819), 2,4,6-trimethylbenzyldiphenyl phosphine oxide, 2,4, Examples include 6-trimethylbenzoyl diphenylphosphine oxide, benzoin methyl ester, camphorquinone, and ethyl 4-(N,N-dimethylamino)benzoate, and can be used alone or in combination. Examples of commercially available visible light photoinitiators include Irgacure 819, Irgacure 1700, Irgacure 1800, Irgacure 819, Irgacure 1850 (manufacturer: Ciba Specialty Chemicals), Lucirin TPO initiator, etc. It is not limited to this, and may include one or more types of these.

In one embodiment, the composition for forming a silicone hydrogel contact lens may include 0.1 to 10% by weight of the initiator.

In one embodiment, the composition for forming a silicone hydrogel contact lens can be added to the composition for manufacturing a contact lens, such as a UV blocker, pigment, antioxidant, plasticizer, wetting agent, lubricant, viscosity reducer, compatibility increaser, etc. It may further contain substances known as additives.

The composition for forming silicone hydrogel contact lenses can be used to manufacture silicone hydrogel contact lenses using a generally known process for manufacturing contact lenses.

For example, the composition for forming a silicone hydrogel contact lens, formulated as described in detail above, is injected into a mold, polymerized using heat or ultraviolet or infrared light to form a lens, and then dried. Silicone hydrogel contact lenses can be manufactured by separating the lens from the mold and going through a hydration process.

The silicone hydrogel contact lens manufactured from the composition for forming the silicone hydrogel contact lens described in detail above exhibits physical properties that simultaneously satisfy high oxygen permeability and high moisture content.

In one embodiment, the silicone hydrogel contact lens has a moisture content in the range of 40% to 65% and an oxygen permeability of Dk 70 to Dk 120.

In one embodiment, the silicone hydrogel contact lens has a moisture content in the range of 50% to 60% and an oxygen permeability of Dk 80 to Dk 115.

In one embodiment, the silicone hydrogel contact lens has a moisture content in the range of 50% to 55% and an oxygen permeability of Dk 80 to Dk 115.

As described above, by appropriately mixing the silicone hydrogel contact lenses in consideration of the physical properties of the contact lenses to be manufactured, it is possible to obtain the silicone hydrogel contact lenses that take into account durability such as strength, elongation, and Young's modulus as well as moisture content and oxygen permeability.

In one embodiment, the silicone hydrogel contact lens has a tensile strength of 4 kgf/mm ² to 8 kgf/mm ² , an elongation of 100% to 200%, and a tensile modulus of elasticity of 0.3 kgf/mm ² to 1.0 kgf/ _mm ² , ^{and the oxygen permeability} _is 70 )] and has a moisture content of 45% to 65%.

Hereinafter, examples and comparative examples of the present invention will be described. The following example is only an example of the present invention, and the present invention is not limited to the following example.

(Example)

Example 1

As a silicon-containing macromonomer, a compound represented by the following formula (11) (weight average molecular weight 1000 Da) 30% by weight, as a hydrophilic monomer (NVP) 45% by weight, polyethylene glycol (weight average molecular weight 200 g/mol) 4% by weight, silicon A composition for forming a silicone hydrogel contact lens was prepared by mixing 19% by weight of the monomer (SiGMA), 1% by weight of the crosslinker (TEGDMA), and 1% by weight of the initiator (AIBN).

The composition for forming a silicone hydrogel contact lens was injected into a polypropylene mold, thermally polymerized at 110° C. to prepare a lens, dried, and separated from the mold. The separated lenses were hydrated in saline solution and sterilized at 120°C to prepare silicone hydrogel contact lenses.

<Formula 11>

In Formula 11 above,

R ₁ to R ₄ are methyl groups, R ₅ is a butyl group, and x=1 and y=15.

Example 2

A silicone hydrogel contact lens was manufactured in the same manner except that polyethylene glycol (weight average molecular weight 400 g/mol) was used instead of polyethylene glycol (weight average molecular weight 200 g/mol) used in Example 1.

Example 3

A silicone hydrogel contact lens was manufactured in the same manner except that polyethylene glycol (weight average molecular weight 1000 g/mol) was used instead of polyethylene glycol (weight average molecular weight 200 g/mol) used in Example 1.

Example 4

A silicone hydrogel contact lens was prepared in the same manner, except that a compound represented by the following formula (12) (weight average molecular weight 2000 g/mol) was used instead of the silicone-containing macromonomer used in Example 1.

<Formula 12>

In Formula 12 above,

R ₁ to R ₂ are methyl groups, R ₃ is an ethyl group substituted with trifluoro methyl group, R ₄ and R ₆ are methyl groups, R ₅ is an ethyl group substituted with polyethylene oxide, x=y=1, o=52, p=4, q=5.

Example 5

A silicone hydrogel contact lens was manufactured in the same manner except that polyethylene glycol (weight average molecular weight 400 g/mol) was used instead of polyethylene glycol (weight average molecular weight 200 g/mol) used in Example 4.

Example 6

A silicone hydrogel contact lens was manufactured in the same manner except that polyethylene glycol (weight average molecular weight 1000 g/mol) was used instead of polyethylene glycol (weight average molecular weight 200 g/mol) used in Example 4.

Example 7

A silicone hydrogel contact lens was manufactured in the same manner except that polyethylene glycol (weight average molecular weight 6000 g/mol) was used instead of polyethylene glycol (weight average molecular weight 200 g/mol) used in Example 4.

Example 8

A silicone hydrogel contact lens was manufactured in the same manner, except that polydimethylsiloxane (mPDMS, weight average molecular weight 800 Da) represented by the following formula (13) was used instead of the silicone-containing macromonomer used in Example 1.

<Formula 13>

In Formula 13 above,

R ₁ to R ₄ are methyl groups, R ₅ is a butyl group, x=3, and y=6.

Example 9

A silicone hydrogel contact lens was prepared in the same manner except that polyethylene glycol (weight average molecular weight 400 g/mol) was used instead of polyethylene glycol (weight average molecular weight 200 g/mol) used in Example 8.

Example 10

A silicone hydrogel contact lens was manufactured in the same manner as in Example 8, except that polyethylene glycol (weight average molecular weight 1000 g/mol) was used instead of polyethylene glycol (weight average molecular weight 200 g/mol).

Evaluation example 1

The physical properties of the silicone hydrogel contact lenses prepared with the various compositions for forming silicone hydrogel contact lenses prepared in Examples 1 to 10 were evaluated by the following method and are listed in Table 1.

(Strength, elongation, Young’s modulus evaluation)

Using a specimen that meets ASTM standards, install a jig for tensile testing at both ends of the specimen. After installation is complete, a load is applied to the jig at a certain speed and the mechanical properties of the sample are measured through the deformation that appears in the sample. Depending on the characteristics of each specimen, deformation or fracture occurs depending on the force applied, which are called tensile strain and tensile stress, respectively. The property of being deformed when a load is applied and then returning to its original form when the load is removed is called elasticity. The slope in the elastic region can be expressed as Young's modulus. In the case of elongation, it is defined as ε=ΔL/L0 as the ratio of the change (change in length of the specimen to the applied force) ΔL to the original gauge length of the specimen (the initial specimen length before force is applied to the specimen) L0, and is generally defined as ε=ΔL/L0. It is expressed as a percentage.

(moisture content)

The moisture content of the lens was measured using gravimetry. Remove moisture from the lens surface and measure its weight. Dry at 100 ℃ to 110 ℃ (60 ℃ ± 5 ℃ if the lens material is denatured) until there is no change in weight and then measure the weight. Lenses are used in sizes from 100 mg to 300 mg, and the weight is measured in units of 0.1 mg. Moisture content (W _H20 ) is calculated as a percentage using the following formula.

(m1: Lens weight before drying, m2: Lens weight after drying)

(Oxygen permeability)

The oxygen permeability (Dk) of a lens is expressed by the diffusion coefficient (D), which is the ability to pass through the material, and the dissolution coefficient (k), which indicates the degree to which oxygen dissolves in the material. In the present invention, measurement was performed using a polarographic method according to ISO 18369.

division robbery
[kgf/mm ² ] elongation
[%] Young's modulus
[kgf/mm ² ] Oxygen permeability (Dk)
10 ^-11 (cm ² /s)[mL O ₂ /(mL·mmHg)] moisture content
(%) Example 1 6.47 174.17 0.46 96.76 53.72 Example 2 6.38 170.16 0.41 98.00 53.14 Example 3 7.08 177.91 0.44 99.35 53.76 Example 4 6.79 136.61 0.57 81.66 49.31 Example 5 6.30 136.59 0.62 82.36 49.58 Example 6 7.36 136.05 0.51 80.71 49.13 Example 7 6.43 138.98 0.67 79.78 48.70 Example 8 10.49 150.29 1.56 80.73 43.59 Example 9 10.35 143.68 1.29 80.93 43.33 Example 10 11.07 158.69 1.41 79.62 44.45

As described above, the present invention has been described with reference to the embodiments, but the present invention is not limited to the embodiments disclosed herein, and various modifications may be made by those skilled in the art within the scope of the technical idea of the present invention. It is obvious that it can be done. In addition, although the operational effects according to the configuration of the present invention were not explicitly described and explained in the above description of the embodiments of the present invention, it is natural that the predictable effects due to the configuration should also be recognized.

Claims (15)

Silicone hydrogel contact lenses comprising a polymer of silicon-containing macromers and polyethylene glycol.
According to paragraph 1,
The silicon-containing macromonomer includes a siloxane chain and a urethane bond and has one or two acrylic functional groups.
Silicone hydrogel contact lenses.
According to paragraph 1,
The polyethylene glycol has a weight average molecular weight of 200 to 6000 g/mol.
Silicone hydrogel contact lenses.
According to paragraph 1,
The polymer of the silicon-containing macromonomer is a hydrophilic monomer, a silicon-containing monomer, or a copolymer of all of these.
Silicone hydrogel contact lenses.
According to paragraph 4,
The hydrophilic monomers include N,N-dimethylacrylamide, 2-hydroxyethyl methacrylate, glycerol monomethacrylate, 2-hydroxyethyl methacrylamide, polyethylene glycol monomethacrylate, methacrylic acid, acrylic acid, N -Vinyl pyrrolidone, N-vinyl-N-methyl acetamide, N-vinyl-N-ethyl acetamide, N-vinyl-N-ethyl formamide, N-vinyl formamide and a group consisting of combinations thereof containing at least one selected from
Silicone hydrogel contact lenses.
According to paragraph 4,
The silicon-containing monomers include α,ω-bismethacryloxypropylpolydimethylsiloxane (SiGMA), 3-methacryloxypropyltris(trimethylsiloxy)silane (TRIS), monomethacryloxypropyl terminated polydimethylsiloxane, and polydimethylsiloxane. Containing at least one selected from the group consisting of siloxane, 3-methacryloxypropylbis(trimethylsiloxy)methylsilane, methacryloxypropylpentamethyl disiloxane, and combinations thereof.
Silicone hydrogel contact lenses.
According to paragraph 1,
It has a water content in the range of 40% to 65% and an oxygen permeability (Dk) of 70 to 120.
Silicone hydrogel contact lenses.
According to paragraph 1,
The tensile strength is 4 kgf/mm ² to 8 kgf/mm ² , the elongation is 100% to 200%, the tensile modulus of elasticity is 0.3 kgf/mm ² to 1.0 kgf/mm ² , and the oxygen permeability is 70 × 10 ^-11. (cm ² /s) [ml O ₂ /(ml·mmHg)] to 120 × 10 ^-11 (cm ² /s) [ml O ₂ /(ml·mmHg)], and the moisture content is 45% to 65%.
Silicone hydrogel contact lenses.
A composition for forming a silicone hydrogel contact lens comprising a silicone-containing macromonomer and polyethylene glycol.
According to clause 9,
The silicon-containing macromonomer includes a siloxane chain and a urethane bond and has one or two acrylic functional groups.
Composition for forming silicone hydrogel contact lenses.
According to clause 9,
The polyethylene glycol has a weight average molecular weight of 200 to 6000 g/mol.
Composition for forming silicone hydrogel contact lenses.
According to clause 9,
10 to 40% by weight of the silicon-containing macromonomer;
1 to 20% by weight of the polyethylene glycol;
10 to 50% by weight of hydrophilic monomer;
10 to 20% by weight of silicone-containing monomer; and
The remainder of additives including crosslinking agent and initiator;
Composition for forming silicone hydrogel contact lenses.
According to clause 12,
The hydrophilic monomers include N,N-dimethylacrylamide, 2-hydroxyethyl methacrylate, glycerol monomethacrylate, 2-hydroxyethyl methacrylamide, polyethylene glycol monomethacrylate, methacrylic acid, acrylic acid, N -Vinylpyrrolidone, N-vinyl-N-methyl acetamide, N-vinyl-N-ethylacetamide, N-vinyl-N-ethylformamide, N-vinylformamide, and a group consisting of combinations thereof containing at least one selected from
Composition for forming silicone hydrogel contact lenses.
According to clause 12,
The silicon-containing monomers include α,ω-bismethacryloxypropylpolydimethylsiloxane (SiGMA), 3-methacryloxypropyltris(trimethylsiloxy)silane (TRIS), monomethacryloxypropyl terminated polydimethylsiloxane, and polydimethylsiloxane. Containing at least one selected from the group consisting of siloxane, 3-methacryloxypropylbis(trimethylsiloxy)methylsilane, methacryloxypropylpentamethyl disiloxane, and combinations thereof.
Composition for forming silicone hydrogel contact lenses.
According to clause 9,
The composition for forming a silicone hydrogel contact lens further comprises at least one selected from the group consisting of a UV blocker, a pigment, and a combination thereof.
Composition for forming silicone hydrogel contact lenses.