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JP-2026514358-A - Silicone hydrogel

JP2026514358AJP 2026514358 AJP2026514358 AJP 2026514358AJP-2026514358-A

Abstract

Silicone hydrogels are composed of one or more monofunctional silicone monomers represented by the structure of formula I (a) [Chemical Formula 1] ( b ) a polymerization product of a monomer mixture containing one or more silicone hydrogel - forming silicone comonomers . ​ ​ ​ ​ [Selection Diagram] None

Inventors

  • ディベラ、ジェイムズ アンソニー ジュニア
  • エーハン、ウェンディ ジー．
  • アワスティー、アロク クマール

Assignees

  • ボシュ ＋ ロム アイルランド リミテッド

Dates

Publication Date
20260511
Application Date
20240131
Priority Date
20230322

Claims (20)

  1. A silicone hydrogel which is a polymerization product of a monomer mixture, wherein the monomer mixture is (a) One or more monofunctional silicone monomers represented by the structure of formula I ( b ) A silicone hydrogel comprising one or more silicone hydrogel - forming silicone comonomers . ​ ​ ​ ​ ​ ​ ​ ​
  2. The silicone hydrogel according to claim 1, wherein in the monofunctional silicone monomer, R1 , R2 , R3 , and R4 are independently hydrogen, a C1 - C12 alkyl group, a C1 - C12 haloalkyl group, a C3 - C12 cycloalkyl group, a C3 - C12 heterocycloalkyl group, a C2 - C12 alkenyl group, a C2 - C12 haloalkenyl group, a C6 - C12 aromatic group, and a C6 - C12 heteroaromatic group, and R5 , R6 , and R7 are independently linear or branched C1 - C12 alkyl groups, x is 1 to 6, and y is 3 to 15.
  3. The silicone hydrogel according to claim 1, wherein in the monofunctional silicone monomer, R1 , R2 , R3 , and R4 are independently hydrogen and a C1 - C6 alkyl group, R5 , R6 , and R7 are independently linear or branched C1 - C6 alkyl groups, x is 1 to 6, and y is 3 to 15.
  4. The silicone hydrogel according to claim 1, wherein in the monofunctional silicone monomer, R1 , R2 , R3 , and R4 are independently C1 - C3 alkyl groups, R5 and R6 are independently C1 - C3 alkyl groups, R7 is a linear or branched C3 - C6 alkyl group, x is 2-4, and y is 3-15.
  5. The silicone hydrogel according to claim 1, wherein in the monofunctional silicone monomer, R1 , R2 , R3 , R4 , R5 , and R6 are methyl, R7 is a linear or branched C3 - C6 alkyl group, x is 2-4, and y is 3-15.
  6. The silicone hydrogel according to any one of claims 1 to 5, wherein the one or more silicone hydrogel-forming silicone comonomers comprise one or more non-bulky organosilicon-containing monomers.
  7. The silicone hydrogel according to claim 6, wherein the one or more non-bulky organosilicon-containing monomers contain at least one [siloxanil] or at least one [silyl-alkyl-siloxanil] repeating unit in the monomer, macromer, or prepolymer.
  8. The aforementioned one or more non-bulky organosilicon-containing monomers include one or more non-bulky organosilicon-containing monomers represented by the structure of formula I: The silicone hydrogel according to claim 6, wherein L is an ethylenically unsaturated polymerizable group, V is a linking group or bond, R1 , R2 , R3 , R4 , R5 , R6 , R7 , R8 , and R9 are independently hydrogen, alkyl group, haloalkyl group, cycloalkyl group, heterocycloalkyl group, alkenyl group, haloalkenyl group, or aryl group, R10 and R11 are independently hydrogen or alkyl group (at least one of R10 and R11 is hydrogen), y is 2 to 7, and n is 1 to 100.
  9. The silicone hydrogel according to claim 8, wherein V is a (meth)acrylate, L is a C1 - C12 alkylene group, R1 , R2 , R3 , R4 , R5 , R6 , R7 , R8 and R9 are independently C1 - C12 alkyl groups, R10 and R11 are independently H or C1 - C12 alkyl groups, y is 2-7, and n is 3-8.
  10. The silicone hydrogel according to claim 8, wherein V is (meth)acrylate, L is a C1 - C6 alkyl group, R1 , R2 , R3 , R4 , R5 , R6 , R7 , R8 and R9 are independently a C1 - C6 alkyl group, R10 and R11 are independently H or a C1 - C6 alkyl group, y is 2-7, and n is 1-20.
  11. The one or more silicone hydrogel-forming silicone comonomers include one or more polysiloxane prepolymers represented by the structure of formula III: A silicone hydrogel according to any one of claims 1 to 10, wherein each V is independently a reactive functional terminal group, R17 to R22 are independently linear or branched, substituted or unsubstituted C1 to C30 alkyl groups, substituted or unsubstituted C3 to C30 cycloalkyl groups, substituted or unsubstituted C4 to C30 cycloalkylalkyl groups, substituted or unsubstituted C3 to C30 cycloalkenyl groups, substituted or unsubstituted C6 to C30 aryl groups, and substituted or unsubstituted C7 to C30 arylalkyl groups, and L is a linking group.
  12. The silicone hydrogel according to claim 11, wherein V is an amine-containing reactive functional terminal group.
  13. The silicone hydrogel according to claim 12, wherein the amine-containing reactive functional terminal group is a (meth)acrylamide-containing reactive functional terminal group.
  14. The monomer mixture (a) a silicone hydrogel according to any one of claims 1 to 13, comprising about 5% to about 40% by weight of one or more monofunctional silicone monomers based on the total weight of the monomer mixture, and (b) a silicone hydrogel according to any one of claims 1 to 13, comprising about 10% to about 60% by weight of one or more silicone hydrogel-forming silicone comonomers based on the total weight of the monomer mixture.
  15. The monomer mixture (a) a silicone hydrogel according to any one of claims 1 to 13, comprising about 7% to about 15% by weight of one or more monofunctional silicone monomers based on the total weight of the monomer mixture, and (b) a silicone hydrogel according to any one of claims 1 to 13, comprising about 15% to about 50% by weight of one or more silicone hydrogel-forming silicone comonomers based on the total weight of the monomer mixture.
  16. The silicone hydrogel according to any one of claims 1 to 15, wherein the monomer mixture further comprises one or more hydrophilic comonomers.
  17. The silicone hydrogel according to claim 16, wherein the one or more hydrophilic comonomers are selected from the group consisting of acrylamide, vinyl lactam, and hydroxyl group-containing (meth)acrylate.
  18. The monomer mixture The silicone hydrogel according to claim 16 or 17, comprising about 20% to 50% by weight of one or more hydrophilic comonomers based on the total weight of the monomer mixture.
  19. The silicone hydrogel according to any one of claims 1 to 18, wherein the monomer mixture further comprises one or more crosslinking agents, one or more reactive ultraviolet absorbers, and one or more reactive blue light absorbers.
  20. A silicone hydrogel according to any one of claims 1 to 19, having an equilibrium water content of approximately 50% to approximately 80% by weight.

Description

Priority Claim This application claims priority to U.S. Provisional Patent Application No. 63/453,851, entitled “Silicone Hydrogels,” filed on 22 March 2023, the entirety of which is incorporated herein by reference. Hydrogels are a desirable class of materials for many biomedical applications, including contact lenses and intraocular lenses. Hydrogels are hydrated, crosslinked polymer systems containing water in equilibrium. Silicone hydrogels are a known class of hydrogels characterized by containing silicone-containing substances. Typically, silicone-containing monomers are copolymerized with hydrophilic monomers by free radical polymerization, with either the silicone-containing monomer or the hydrophilic monomer acting as a crosslinking agent (defined as a monomer having multiple polymerizable functional groups), or another crosslinking agent may be used. In an exemplary embodiment, the silicone hydrogel is: (a) One or more monofunctional silicone monomers represented by the structure of formula I (wherein R1 , R2 , R3 and R4 are independently hydrogen, C1 - C12 alkyl groups, C1 - C12 haloalkyl groups, C3 - C12 cycloalkyl groups, C3- C12 heterocycloalkyl groups, C2 - C12 alkenyl groups, C2 -C12 haloalkenyl groups, C6 - C12 aryl groups and C6 - C12 heteroaryl groups, R5 , R6 and R7 are independently linear or branched C1 - C12 alkyl groups, x is 1-6, and y is 3-15), and (b) A polymerization product of a monomer mixture containing one or more silicone hydrogel-forming silicone comonomers. In another exemplary embodiment, a method for preparing a silicone hydrogel is: (a) Curing a monomer mixture in a mold, wherein the monomer mixture is: (i) One or more monofunctional silicone monomers represented by the structure of formula I (wherein R1, R2 , R3 , R4 , R5 , R6 , R7 , x and y are as defined herein), and (ii) A material containing one or more silicone hydrogel-forming silicone comonomers, which is curable, (b) The process includes releasing the silicone hydrogel from the mold. The various exemplary embodiments described herein relate to silicone hydrogels with improved oxygen permeability and methods for producing the same. Hydrogels are a desirable class of material for contact lenses. Hydrogels are hydrated, cross-linked polymer systems that contain water in equilibrium. Hydrogel lenses offer relatively high oxygen permeability, as well as desirable biocompatibility and comfort. Oxygen permeability (Dk) is a crucial factor in contact lens design for maintaining the eye health of contact lens wearers. For example, contact lenses must allow sufficient oxygen to reach the cornea for long-term corneal health. Since the cornea does not receive oxygen from the blood supply like other tissues, contact lenses must also allow oxygen from the surrounding air to reach the cornea. Because "soft" contact lenses conform closely to the shape of the eye, oxygen cannot easily bypass the lens. Therefore, soft contact lenses must allow oxygen to diffuse through the lens and reach the cornea. Another ophthalmic fit requirement for soft contact lenses is that the lens must not adhere too strongly to the eye. For example, consumers must be able to easily remove the lens from their eye for disinfection, cleaning, or disposal. However, the lens must also be movable on the eye to facilitate tear flow between the lens and the eye. This tear flow allows debris such as foreign particles or dead epithelial cells to be swept away from under the lens and eventually through the tear film. Therefore, contact lenses must not adhere so strongly to the eye that proper movement of the lens on the eye is hindered. Soft contact lens materials are manufactured by polymerizing and crosslinking hydrophilic monomers such as 2-hydroxyethyl methacrylate (HEMA) and N-vinylpyrrolidone (NVP). Polymers produced by polymerizing these hydrophilic monomers exhibit significant hydrophilicity themselves and can absorb large amounts of water into the polymer matrix. Because of their water-absorbing ability, these polymers are often called "hydrogels." These hydrogels are optically transparent and have high hydration water levels, making them useful materials for manufacturing soft contact lenses. However, these hydrogels are known to have low oxygen permeability. Silicone hydrogels (SiHy), such as contact lenses, manufactured from hydrated cross-linked polymer materials containing silicone and a certain amount of water within a lens polymer matrix in equilibrium, are becoming increasingly popular compared to conventional hydrogels due to their high oxygen permeability and minimal adverse effects on corneal health. However, incorporating silicone into contact lens materials can undesirably affect the hydrophilicity and wettability of the silicone hydrogel because silicone is hydrophobic and tends to migrate to the lens surface exposed to air. Therefore, optimal contact lenses must possess at least excellent oxygen permeability and excellent tear film wett