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JP-2026514359-A - Monofunctional silicone monomers and silicone hydrogels formed therefrom

JP2026514359AJP 2026514359 AJP2026514359 AJP 2026514359AJP-2026514359-A

Abstract

Monofunctional silicone monomers are given by formula I: [Chemistry I] It is represented by the structure, In the formula, R1 , R2 , R3 , R4 , R5 , R6 , R7 , x, and y are as defined herein. The optically transparent ophthalmic device is a polymerization product of a monomer mixture comprising (a) one or more monofunctional silicone monomers represented by the structure of formula I, and (b) one or more ophthalmic device-forming hydrophilic 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. Formula I: A monofunctional silicone monomer represented by the structure, A monofunctional silicone monomer in which R1 , R2 , R3 , and R4 are independently hydrogen, alkyl group, haloalkyl group, cycloalkyl group, heterocycloalkyl group, alkenyl group, haloalkenyl group, aryl group, and heteroaryl group, R5 , R6 , and R7 are independently linear or branched alkyl groups, x is 1 to 6, and y is 3 to 5.
  2. The monofunctional silicone monomer according to claim 1, wherein 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 5.
  3. The monofunctional silicone monomer according to claim 1, wherein R1 , R2 , R3 , and R4 are independently hydrogen and C1 - C6 alkyl groups, R5 , R6 , and R7 are independently linear or branched C1 -C6 alkyl groups, x is 1 to 6 , and y is 3 to 5.
  4. The monofunctional silicone monomer according to claim 1, wherein 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 3-5.
  5. The monofunctional silicone monomer according to claim 1, wherein 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 3-5.
  6. An ophthalmic device which is a polymerization product of a monomer mixture, wherein the monomer mixture is (a) Equation I: (b) an ophthalmic device comprising one or more monofunctional silicone monomers represented by the structure (wherein R1 , R2 , R3 and R4 are independently hydrogen, alkyl groups, haloalkyl groups, cycloalkyl groups, heterocycloalkyl groups, alkenyl groups, haloalkenyl groups, aryl groups and heteroaryl groups, R5 , R6 and R7 are independently linear or branched alkyl groups, x is 1 to 6 and y is 3 to 5), and (b) one or more ophthalmic device-forming hydrophilic comonomers.
  7. The ophthalmic device according to claim 6, 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 5.
  8. The ophthalmic device according to claim 6, wherein in the monofunctional silicone monomer, R1 , R2 , R3 , and R4 are independently hydrogen and C1 - C6 alkyl groups, R5 , R6 , and R7 are independently linear or branched C1 - C6 alkyl groups, x is 1 to 6, and y is 3 to 5.
  9. The ophthalmic device according to claim 6, 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 3-5.
  10. The ophthalmic device according to claim 6, 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 3-5.
  11. The ophthalmic device according to any one of claims 6 to 10, wherein the one or more ophthalmic device-forming hydrophilic comonomers are selected from the group consisting of unsaturated carboxylic acids, acrylamides, vinyl lactams, hydroxyl group-containing (meth)acrylates, hydrophilic vinyl carbonates, hydrophilic vinyl carbamates, hydrophilic oxazolones, and poly(alkene glycols) functionalized with polymerizable groups.
  12. The ophthalmic device according to any one of claims 6 to 10, wherein the one or more ophthalmic device-forming hydrophilic comonomers are selected from the group consisting of acrylamide, vinyl lactam, and hydroxyl group-containing (meth)acrylate.
  13. The monomer mixture is An ophthalmic device according to any one of claims 6 to 12, comprising, based on the total weight of the monomer mixture, about 1% by weight to about 40% by weight of one or more monofunctional silicone monomers, and, based on the total weight of the monomer mixture, about 10% by weight to about 80% by weight of one or more ophthalmic device-forming hydrophilic comonomers.
  14. The ophthalmic device according to any one of claims 6 to 13, wherein the monomer mixture further comprises one or more non-functionalized comfort polymers.
  15. The ophthalmic device according to claim 14, wherein the one or more non-functionalized comfort polymers include a polyvinylpyrrolidone polymer.
  16. The ophthalmic device according to claim 15, wherein the weight-average molecular weight of the polyvinylpyrrolidone polymer is at least about 10,000.
  17. The ophthalmic device according to claim 15, wherein the weight-average molecular weight of the polyvinylpyrrolidone polymer is approximately 10,000 to approximately 250,000.
  18. The ophthalmic device according to any one of claims 15 to 17, wherein the one or more non-functionalized comfort polymers are present in the monomer mixture in an amount of at least 6% by weight, based on the total weight of the monomer mixture.
  19. The ophthalmic device according to any one of claims 15 to 17, wherein the one or more non-functionalized comfort polymers are present in the monomer mixture in an amount ranging from 6% to about 10% by weight, based on the total weight of the monomer mixture.
  20. The ophthalmic device according to any one of claims 6 to 19, wherein the monomer mixture further comprises one or more functionalized comfort polymers.

Description

Priority Claim This application claims priority to U.S. Provisional Patent Application No. 63/453,850, “Monofunctional Silicone Monomers and Silicone Hydrogels Formed Therefrom,” filed on 22 March 2023, the entire contents of which are incorporated herein by reference. In the field of biomedical devices such as contact lenses, various physical and chemical properties, such as optical clarity, oxygen permeability, wettability, material strength, and stability, are only a fraction of the factors that must be carefully balanced to provide a usable contact lens. For example, good oxygen permeability is a crucial property for any contact lens material, as the cornea receives its oxygen supply solely from contact with the atmosphere. Wettability is also important, as a lens that is not sufficiently wet will not remain lubricated and therefore cannot be comfortably worn in the eye. Thus, an optimal contact lens would possess at least excellent oxygen permeability and excellent tear film wettability. Hydrogels are a desirable class of materials for many biomedical applications, including contact lenses and intraocular lenses. Hydrogels are hydrated crosslinked polymer systems that contain water at equilibrium. Silicone hydrogels are a known class of hydrogels characterized by the inclusion of a silicone-containing substance. Typically, the silicone-containing monomer is copolymerized with a hydrophilic monomer by free radical polymerization, with either the silicone-containing monomer or the hydrophilic monomer acting as a crosslinker (a crosslinker is defined as a monomer having multiple polymerizable functional groups), or a separate crosslinker may be used. An advantage of silicone hydrogels over non-silicone hydrogels is that, due to the inclusion of the silicone-containing monomer, silicone hydrogels generally have higher oxygen permeability. According to an exemplary embodiment, the monofunctional silicone monomer is of formula I: It is represented by the structure, In the formula, 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 aryl group, and a C6 - C12 heteroaryl group; R5 , R6 , and R7 are independently linear or branched C1 - C12 alkyl groups; x is 1-6; and y is 3-5. According to another exemplary embodiment, an ophthalmic device is a polymerization product of a monomer mixture, wherein the monomer mixture is: (a) Equation I: One or more monofunctional silicone monomers represented by the structure (wherein R1 , R2, R3 , R4 , R5 , R6 , R7 , x and y are as defined herein), and (b) An ophthalmic device comprising one or more ophthalmic device-forming hydrophilic comonomers. According to yet another exemplary embodiment, an ophthalmic device is a polymerization product of a monomer mixture, wherein the monomer mixture is: (a) Equation I: One or more monofunctional silicone monomers represented by the structure (wherein R1 , R2, R3 , R4 , R5 , R6 , R7 , x and y are as defined herein), (b) One or more ophthalmic device-forming hydrophilic comonomers, and (c) An ophthalmic device comprising one or more non-functionalized comfort polymers. According to yet another exemplary embodiment, a method for fabricating an ophthalmic device 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 curing agent containing one or more ophthalmic device-forming hydrophilic comonomers. (b) Including dry demolding of ophthalmic devices from molds. The various exemplary embodiments described herein relate to the use of silicone monomers and silicone hydrogels with improved optical transparency in the formation of ophthalmic devices. Silicone hydrogels (SiHy), such as contact lenses made from hydrated crosslinked polymer materials containing silicone and a certain amount of water in equilibrium within the polymer matrix of the lens, are becoming increasingly popular due to their high oxygen permeability, which minimizes adverse effects on corneal health. However, incorporating silicone into contact lens materials can undesirably affect the hydrophilicity and wettability of the silicone hydrogel. This is because silicone is hydrophobic and has a strong tendency to migrate to the lens surface exposed to air. Therefore, contact lens manufacturers have made considerable efforts to develop SiHy contact lenses with hydrophilic and wettable surfaces. One method for modifying the hydrophilicity and wettability of SiHy contact lenses is to add hydrophilic monomers to the monomer mixture used to form the SiHy contact lenses. However, it has been discovered that adding monofunctional silicone monomers to a monomer mixture containing one or more ophthalmic devi