Search

JP-2026514312-A - Grafted ophthalmic devices containing inactivation regions, and processes for their preparation and use.

JP2026514312AJP 2026514312 AJP2026514312 AJP 2026514312AJP-2026514312-A

Abstract

An ophthalmic device is disclosed, the ophthalmic device comprising: (a) a step of providing a reactive composition, the reactive composition comprising (i) a polymerization initiator capable of forming two or more free radical groups upon first activation, wherein at least one of the free radical groups is further activatable by subsequent activation, (ii) one or more ethylenically unsaturated compounds, and (iii) a crosslinking agent; (b) a step of subjecting the reactive composition to a first activation step such that the reactive composition polymerizes thereto form a crosslinked substrate network containing covalently bonded activatable free radical initiators; and (c) inactivating at least a portion of the covalently bonded activatable free radical initiators in one or more selected regions of the crosslinked substrate network. An ophthalmic device manufactured by a process comprising: (d) a step of ensuring that the crosslinked substrate network contains retained covalently bonded activatable free radical initiators outside one or more selected regions and optionally within one or more selected regions; (b) a step of contacting the crosslinked substrate network with a grafting composition containing one or more ethylenically unsaturated compounds, wherein the contact is carried out under conditions such that the grafting composition penetrates into the crosslinked substrate network; and (e) a step of activating the retained covalently bonded activatable free radical initiators so that the grafting composition polymerizes with the crosslinked substrate network, thereby forming a grafted polymer network outside the selected regions and optionally partially within the selected regions.

Inventors

  • ウィドマン・マイケル・エフ
  • マハルビ・グラーム

Assignees

  • ジョンソン・アンド・ジョンソン・ビジョン・ケア・インコーポレイテッド

Dates

Publication Date
20260511
Application Date
20240221
Priority Date
20240130

Claims (20)

  1. An ophthalmic device, a) A step of providing a reactive composition, wherein the reactive composition comprises (i) a polymerization initiator capable of forming two or more free radical groups upon first activation, wherein at least one of the free radical groups is further activatable by subsequent activation, (ii) one or more ethylenically unsaturated compounds, and (iii) a crosslinking agent. b) A step of subjecting the reactive composition to a first activation step, wherein the reactive composition polymerizes thereto to form a crosslinked substrate network containing covalently bonded activatable free radical initiators, c) A step of inactivating at least a portion of the covalently bonded activatable free radical initiator in one or more selected regions of the crosslinked substrate network so that the crosslinked substrate network contains retained covalently bonded activatable free radical initiator outside of the one or more selected regions, d) A step of contacting the crosslinked substrate network with a grafting composition containing one or more ethylenically unsaturated compounds, wherein the contact is carried out under conditions such that the grafting composition penetrates into the crosslinked substrate network. e) A step of activating the retained covalently bonded activatable free radical initiator so that the grafted composition polymerizes with the crosslinked substrate network, thereby forming a grafted polymer network outside the selected region, An ophthalmic device formed by a process that includes [a specific term].
  2. The ophthalmic apparatus according to claim 1, wherein the inactivation in step (c) is spatially varied within the ophthalmic apparatus.
  3. The ophthalmic apparatus according to claim 1 or 2, wherein the inactivation step (c) is achieved by irradiation at a wavelength capable of activating the initiator, and the initiation is performed in an atmosphere containing oxygen gas.
  4. The ophthalmic device according to claim 1, wherein the grafting composition in step (d) contains a crosslinking agent.
  5. The ophthalmic device according to claim 1, wherein the grafting composition in step (d) does not contain a crosslinking agent.
  6. The ophthalmic device according to claim 1, wherein in step (c), only a portion of the covalently bonded activatable free radical initiator is inactivated in the selected region, and step (e) partially comprises forming a grafted network within the selected region.
  7. The ophthalmic apparatus according to claim 1, wherein the one or more ethylenically unsaturated compounds in step (a) comprises one or more polymerizable groups independently selected from (meth)acrylate, (meth)acrylamide, styryl, vinyl, N-vinyl lactam, N - vinylamide, O -vinyl ether, O-vinyl carbonate, O-vinylcarbamate, C2-12 alkenyl, C2-12 alkenylphenyl, C2-12 alkenylnaphthyl, and C2-6 alkenylphenyl-C1-6 alkyl.
  8. The ophthalmic apparatus according to claim 1, wherein the one or more ethylenically unsaturated compounds in step (d) comprise one or more polymerizable groups independently selected from (meth)acrylate, (meth)acrylamide, styryl, vinyl, N-vinyl lactam, N - vinylamide, O -vinyl ether, O-vinyl carbonate, O-vinylcarbamate, C2-12 alkenyl, C2-12 alkenylphenyl, C2-12 alkenylnaphthyl, and C2-6 alkenylphenyl-C1-6 alkyl.
  9. The polymerization initiator is a bisacylphosphine oxide, a bisacylphosphine oxide, a diazo compound, a diperoxide compound, azobis(monoacylphosphine oxide), azobis(monoacylphosphine oxide), peroxybis(monoacylphosphine oxide), peroxybis(monoacylphosphine oxide), azobis(α-hydroxyketone), peroxybis(α-hydroxyketone), azobis(1,2-diketone), peroxybis(1,2-diketone), a germanium-based compound, tert-butyl 7-methyl-7-(tert-butylazo)peroxyoctanoate, or a combination thereof, as described in claim 1.
  10. The ophthalmic device according to claim 1, wherein the polymerization initiator is bisacylphosphine oxide or bis(acyl)phosphine oxide.
  11. The ophthalmic device according to claim 1, wherein the hydrogel is in the form of a hydrogel, the reactive composition contains one or more silicone-containing components, and the grafting composition contains one or more hydrophilic reactive components.
  12. The ophthalmic device according to claim 1, wherein the reactive composition, the grafting composition, or both the reactive composition and the grafting composition contain one or more additives selected from UV absorbers, phototautomorphic compounds, pharmaceutical compounds, nutritional supplements, antimicrobial compounds, reactive colorants, pigments, copolymerizable dyes, nonpolymerizable dyes, release agents, wetting agents, and other release agents.
  13. The ophthalmic apparatus according to claim 1, further comprising the step of contacting the crosslinked substrate network with a second grafting composition containing one or more ethylenically unsaturated compounds, thereby activating retained covalently bonded, activatable free radical initiators, so that the second grafting composition polymerizes with the crosslinked substrate network outside the selected region and optionally partially within the selected region.
  14. The ophthalmic device according to claim 1, wherein steps (a) and (b) are performed within a mold assembly comprising a front mold and a rear mold, the front mold and the rear mold defining and sealing a cavity in the shape of the ophthalmic device between them, and process steps (c), (d), and (e) are performed within the mold assembly after the rear mold has been removed.
  15. The ophthalmic device according to claim 1, wherein the ophthalmic device is selected from the group consisting of contact lenses, intraocular lenses, punctal plugs, and ocular implants.
  16. The ophthalmic device according to claim 15, wherein the ophthalmic device is a contact lens or an intraocular lens.
  17. An ophthalmic device which is a reaction product of a composition, wherein the composition is a) A crosslinked substrate network containing covalently bonded activatable free radical initiators outside of one or more select regions and optionally partially within said one or more select regions, b) An ophthalmic device comprising a grafting composition containing one or more ethylenically unsaturated compounds, wherein the grafting composition is localized in the crosslinked substrate network that holds covalently activatable free radical initiators.
  18. The ophthalmic device according to claim 17, wherein the concentration of the retained covalently bonded, activatable free radical initiator varies spatially within the crosslinked substrate network.
  19. The ophthalmic device according to claim 17 or 18, wherein the crosslinked substrate network is a reaction product of a reactive composition comprising (i) a polymerization initiator capable of forming two or more free radical groups upon first activation, wherein at least one of the free radical groups is further activatable by subsequent activation, (ii) one or more ethylenically unsaturated compounds, and (iii) a crosslinking agent.
  20. The polymerization initiator is a bisacylphosphine oxide, a bisacylphosphine oxide, a diazo compound, a diperoxide compound, azobis(monoacylphosphine oxide), azobis(monoacylphosphine oxide), peroxybis(monoacylphosphine oxide), peroxybis(monoacylphosphine oxide), azobis(α-hydroxyketone), peroxybis(α-hydroxyketone), azobis(1,2-diketone), peroxybis(1,2-diketone), a germanium-based compound, tert-butyl 7-methyl-7-(tert-butylazo)peroxyoctanoate, or a combination thereof, as described in claim 19.

Description

(Cross-reference of related applications) This application claims priority to U.S. Patent Application No. 18/426,780, filed on 30 January 2024, and U.S. Provisional Patent Application No. 63/492,499, filed on 28 March 2023, both of which are incorporated herein by reference. (Field of invention) The present invention relates to ophthalmic devices such as contact lenses containing a grafted polymer network, and to processes for preparing and using ophthalmic devices. The development of polymer materials prepared from individual components that contribute to desired properties is an ongoing goal in many product areas. For example, polymer materials exhibiting oxygen permeability and hydrophilicity are desirable for numerous applications in the medical device field, such as ophthalmic devices. A common challenge in forming polymer materials that attempt to combine properties is that the individual components from which the final material is made often do not mix easily with each other. For example, in the field of contact lenses, silicone hydrogels have been found to provide lenses with significantly increased oxygen permeability, and therefore can reduce corneal edema and hypervascularity that may be associated with conventional hydrogel lenses. Silicone hydrogels have generally been prepared by polymerizing a mixture containing at least one silicone-containing monomer or silicone-containing reactive macromer and at least one hydrophilic monomer. However, because the silicone and hydrophilic components are often miscible, silicone hydrogel lenses can be difficult to manufacture. In addition to the overall compatibility of the reactants, in some applications, it is desirable to form products from different materials, and that these materials be localized to specific areas rather than dispersed throughout. For example, in the field of ophthalmic devices, processes that allow for localized modifications of devices (such as contact lenses) can enable manufacturers to produce products with customized lens powers or other desirable properties. This document describes a voxel-based lithography apparatus that can be used to implement several embodiments of the present invention.This document illustrates the design of mold jigs according to various embodiments of the present invention.The projection image of the inactivation and grafting process used in Example 1 is shown.Microscopic images of the inactivated and grafted contact lenses from Example 1 are shown.An example of carrying out the method according to the present invention is shown. Unless otherwise specified, all scientific and technical terms used herein have the same meanings as those generally understood by those skilled in the art in the field to which this invention pertains. All publications, patent applications, patents, and other references referenced herein are incorporated herein by reference. Unless otherwise stated, a numerical range, such as "from 2 to 10" or "between 2 and 10," includes the numbers defining that range (e.g., 2 and 10). Unless otherwise stated, ratios, percentages, and parts are expressed by weight. The term "number-average molecular weight" refers to the number-average molecular weight ( Mn ) of the sample. The term "weight-average molecular weight" refers to the weight-average molecular weight ( Mw ) of the sample. The term "polydispersion index" (PDI) refers to the ratio of Mw divided by Mn and represents the molecular weight distribution of the sample. If the type of "molecular weight" is not specified or is not clear from the context, it is intended to mean the number-average molecular weight. As used herein, the term "about" means a range of ±10 percent of the number it modifies. For example, the phrase "about 10" would include both 9 and 11. As used herein, the term "(meth)" refers to an optional methyl substitution. Therefore, terms such as "(meth)acrylate" refer to both methacrylate and acrylate. Regardless of where the chemical structure is described, it should be understood that any combination of disclosed alternative options for substituents in the structure is permitted. Therefore, if a structure contains substituents R * and R ** , each containing a list of three possible groups, then nine combinations are disclosed. The same applies to combinations of properties. The average number of repeating units in a polymer sample is known as the "degree of polymerization." When a common chemical formula for a polymer sample, e.g., [ *** ] n , is used, "n" represents the degree of polymerization of that sample, and the formula should be interpreted as representing the number-average molecular weight of the polymer sample. In this specification, the term "individual" includes humans and vertebrates. As used herein, the term “ophthalmic device” refers to any device located inside or above the eye, including on the surface of the eye, or in any part of the eye. These devices may provide optical correction, cosmetic enhancement