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JP-7857303-B2 - Silicone hydrogel contact lenses

JP7857303B2JP 7857303 B2JP7857303 B2JP 7857303B2JP-7857303-B2

Inventors

  • ピョン スンヒ
  • ラ ミラエ
  • ハム ヒョンウン

Assignees

  • インテロジョ インコーポレーテッド

Dates

Publication Date
20260512
Application Date
20221026
Priority Date
20220520

Claims (15)

  1. A method for manufacturing a silicone hydrogel contact lens having an oxygen permeability of 80 × 10⁻¹¹ (cm² / s) [mlO₂ / (ml·mmHg)] to 120 × 10⁻¹¹ ( cm² / s) [ mlO₂ /(ml·mmHg)] and a water content of 50% to 60% , 10-40% by weight of silicon-containing macromers, A polyethylene glycol having a molecular weight of 200 to 1,000 g/mol in 1 to 20% by weight, The process involves polymerizing a silicone hydrogel contact lens forming composition containing a crosslinking agent and an initiator. In the composition, the difference ΔδD, ΔδP, and ΔδH of the dispersion force (δD), dipole attraction force (δP), and hydrogen bonding force (δH) that determine the Hansen solubility parameter of the silicon-containing macromer and the polyethylene glycol, respectively, satisfies the following conditions: -6.0MPa 1/2 ≦△δD≦1.0MPa 1/2 1.5MPa 1/2 ≦△δP≦3.5MPa 1/2 4.0MPa 1/2 ≦△δH≦8.0MPa 1/2 A method for producing silicone hydrogel contact lenses, wherein the polymerization is carried out in a manner in which at least 95% of the polyethylene glycol is removed from the composition by thermal polymerization at a temperature of 100°C to 110°C or by UV light polymerization.
  2. A method for producing a silicone hydrogel contact lens according to claim 1 , wherein the polyethylene glycol is PEG200, PEG400, or PEG1000.
  3. The method for producing a silicone hydrogel contact lens according to claim 1 , wherein the silicon-containing macromer contains a siloxane chain and has one or two acrylic functional groups.
  4. The method for producing a silicone hydrogel contact lens according to claim 1 , wherein the silicon-containing macromer has a weight-average molecular weight of 500 Da to 2,500 Da.
  5. The method for producing a silicone hydrogel contact lens according to claim 1 , wherein the silicone hydrogel contact lens forming composition further comprises a hydrophilic monomer.
  6. The method for producing a silicone hydrogel contact lens according to claim 5, wherein the hydrophilic monomer is at least one selected from N,N-dimethylacrylamide, 2-hydroxyethyl methacrylate, glycerol monomethacrylate, 2-hydroxyethyl methacrylate, polyethylene glycol monomethacrylate, methacrylic acid, acrylic acid, N-vinylpyrrolidone, N-vinyl-N-methylacetamide, N-vinyl-N-ethylacetamide, N-vinyl-N-ethylformamide, N -vinylformamide, and combinations thereof.
  7. The method for producing a silicone hydrogel contact lens according to claim 5 , wherein the composition for forming the silicone hydrogel contact lens contains 20 to 239 parts by weight of the hydrophilic monomer per 100 parts by weight of the silicon macromer.
  8. The method for producing a silicone hydrogel contact lens according to claim 5 , wherein the silicone hydrogel contact lens forming composition contains 10 to 50% by weight of the hydrophilic monomer.
  9. The method for producing a silicone hydrogel contact lens according to claim 1 , wherein the silicone hydrogel contact lens forming composition further comprises a silicon monomer.
  10. The method for producing a silicone hydrogel contact lens according to claim 9, wherein the silicon-containing monomer is at least one selected from α,ω-bismethacryloxypropyl polydimethylsiloxane (SiGMA), 3-methacryloxypropyl tris(trimethylsiloxy)silane (TRIS), monomethacryloxypropyl-terminated polydimethylsiloxane, polydimethylsiloxane, 3 -methacryloxypropyl bis(trimethylsiloxy)methylsilane, methacryloxypropyl pentamethyldisiloxane, or combinations thereof.
  11. The method for producing a silicone hydrogel contact lens according to claim 9 , wherein the silicone hydrogel contact lens forming composition contains 10 to 20% by weight of the silicon-containing monomer.
  12. The method for producing a silicone hydrogel contact lens according to claim 1, wherein the crosslinking agent comprises at least one selected from allyl methacrylate (AMA), divinylbenzene (DVB), triethylene glycol dimethacrylate (TrEGDMA), triallyl isocyanurate ( TAIC ), ethylene glycol dimethyl acrylate (EGDMA), ethylenediamine dimethacrylamide, glycerol dimethacrylate, and combinations thereof.
  13. The initiators include lauryl peroxide, benzoyl peroxide, isopropyl percarbonate, azobisisobutyronitrile, aromatic α-hydroxyketone, alkoxybenzoin, acetophenone, tert-butylperoxine decanoate, acylphosphine oxide, tertiary amine, diketone, 1-hydroxycyclohexylphenyl ketone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, bis(2,6-dimethoxybenzoyl)-2,4,4-trimethylpentylphosphine oxide (DMBAPO), and bis(2,4,6-trimethylbenzoyl). A method for producing a silicone hydrogel contact lens according to claim 1, comprising at least one selected from phenylphosphine oxide, 2,4,6 -trimethylbenzyldiphenylphosphine oxide, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, benzoin methyl ester, camphorquinone, 4-(N,N-dimethylamino)ethyl benzoate, Irgacure 819, Irgacure 1700, Irgacure 1800, Irgacure 819, Irgacure 1850, Lucilin TPO initiator, and combinations thereof.
  14. The method for producing a silicone hydrogel contact lens according to claim 1 , wherein the silicone hydrogel contact lens forming composition further comprises at least one selected from a UV blocking agent, a pigment, a diluent, and a combination thereof.
  15. The difference between the dispersion force (δD), dipole attractive force (δP), and hydrogen bonding force (δH) that determine the Hansen solubility parameters of the silicon-containing macromer and the polyethylene glycol, ΔδD, ΔδP, and ΔδH, respectively, is: -0.8MPa 1/2 ≦△δD≦0.3MPa 1/2 , 2.0MPa 1/2 ≦△δP≦2.5MPa 1/2 , A method for manufacturing a silicone hydrogel contact lens according to claim 1 , satisfying the condition 4.5 MPa 1/2 ≤ ΔδH ≤ 5.7 MPa 1/2 .

Description

This disclosure relates to a composition for forming silicone hydrogel contact lenses, a silicone hydrogel contact lens manufactured from the composition, the composition, or a method for manufacturing a silicone hydrogel contact lens. Contact lenses are widely used for cosmetic purposes in addition to vision correction, and the market for cosmetic contact lenses continues to grow. Research into developing new cosmetic contact lenses is active, resulting in a constant stream of new products with various physical properties. Zanini et al., U.S. Patent No. 7,789,507, discloses an ophthalmic lens formed from a reaction mixture comprising a high molecular weight hydrophilic polymer, an effective amount of hydroxyl-functionalized silicone-containing monomer, and an effective amount of polyethylene glycol for facilitating lens removal from device-forming mold components, wherein the polyethylene glycol comprises one or more of PEG2000, mPEG, and PEGDME. The embodiments of this disclosure are described below in detail so that they can be readily implemented by those skilled in the art. Because this disclosure can be embodied in various forms, it should not be construed as being limited to the embodiments described herein. The cornea receives oxygen through contact with oxygen dissolved in tears and oxygen in the air, but contact lenses placed on the cornea can potentially obstruct this oxygen supply. Therefore, the oxygen permeability of contact lenses is an important consideration, especially when developing new contact lenses to improve eye health. In the case of contact lens materials, a composition containing a mixture of multiple monomers and an initiator is injected into a mold, and polymerization occurs while crosslinking reactions are triggered by instantaneous energy. The lens functions as a polymer material produced by this polymerization reaction, and the properties of the contact lens, such as refractive index, mechanical strength, wettability, and oxygen permeability, are determined by the components of the composition. <Definition> In this specification, the term "hydrogel" refers to a crosslinked polymer material that, when hydrated, can retain at least 10% by weight of water in the matrix of the crosslinked polymer. In this specification, "silicon-containing macromer" refers to 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- CH2 - CH2 )n-OH. Generally, n has a value of 4 or greater. In this specification, "hydrophilic monomer" refers to a monomer having polymerizable functional groups such as olefin groups and acrylic groups, and hydrophilic functional groups such as hydroxyl groups, amines, and pyrrolidones, and having a molecular weight of less than 500 Da. In this specification, "silicon-containing monomer" refers to a monomer that contains silicon and has an ethylenically unsaturated group, and has a weight-average molecular weight of less than 500 Da. <Silicone hydrogel contact lenses and polymer compositions> This disclosure provides a silicone hydrogel contact lens comprising a polymer composition prepared by polymerization of a silicone hydrogel contact lens forming composition. The silicone hydrogel contact lens forming composition comprises about 10 to about 40% by weight of a silicon-containing macromer, about 1 to about 20% by weight of polyethylene glycol having a molecular weight of about 200 to about 1,000 g/mol, and a crosslinking agent or initiator, wherein the polymerization is carried out by thermal polymerization at a temperature of about 100°C to about 110°C or by UV photopolymerization, in which at least about 95% of the polyethylene glycol is removed from the polymer composition. The polyethylene glycol in the silicone hydrogel contact lens forming composition can be any PEG having a molecular weight of about 200 to about 1,000 g/mol. For the manufacture of silicone hydrogel contact lenses, it is undesirable to use high molecular weight polyethylene glycol, such as 2,000 to 6,000 g/mol. This is because such high molecular weight PEGs are not sufficiently removed from the composition during polymerization, and the resulting polymer cannot achieve desired properties such as high oxygen permeability and high water content. In one embodiment, the polyethylene glycol is selected from the group consisting of PEG200, PEG300, PEG400, PEG600, PEG800, and PEG1000. In a specific embodiment, the polyethylene glycol is PEG200, PEG400, or PEG1000. The polymer composition is prepared by polymerization of a silicone hydrogel contact lens forming composition. In one embodiment, polymerization is carried out by thermal polymerization at a temperature of approximately 100°C to approximately 110°C. In another embodiment, polymerization is carried out by UV photopolymerization. In various embodiments, the polymerization step is c