[go: up one dir, main page]

WO2025012621A1 - Formulation de lentilles de contact et lentille de contact - Google Patents

Formulation de lentilles de contact et lentille de contact Download PDF

Info

Publication number
WO2025012621A1
WO2025012621A1 PCT/GB2024/051767 GB2024051767W WO2025012621A1 WO 2025012621 A1 WO2025012621 A1 WO 2025012621A1 GB 2024051767 W GB2024051767 W GB 2024051767W WO 2025012621 A1 WO2025012621 A1 WO 2025012621A1
Authority
WO
WIPO (PCT)
Prior art keywords
formula
compound
component
formulation
methacrylate
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
PCT/GB2024/051767
Other languages
English (en)
Inventor
Laura SIMPSON
Ian Gibson
Katarzyna PISKORCZYK
David Morsley
William Mitchell
Robert Andrew Broad
Yuwen Liu
Yuan SUN
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
CooperVision International Ltd
Original Assignee
CooperVision International Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from GBGB2311167.7A external-priority patent/GB202311167D0/en
Application filed by CooperVision International Ltd filed Critical CooperVision International Ltd
Publication of WO2025012621A1 publication Critical patent/WO2025012621A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
    • G02B1/041—Lenses
    • G02B1/043—Contact lenses

Definitions

  • the present invention relates to novel silicone hydrogel contact lens formulations, and an ophthalmic lens, particularly a contact lens and more particularly a silicone hydrogel contact lens comprising the reaction product of a polymerizable composition.
  • Silicone hydrogel contact lenses have proven to be acceptable alternatives to hydrogel contact lenses. Contact lens manufacturers are often presented with introducing new contact lenses to satisfy market demand. Thus, there is an ongoing need to develop new silicone hydrogel contact lenses to address this demand.
  • silicone hydrogel contact lenses In the development of silicone hydrogel contact lenses, it is difficult to predict whether a new silicone hydrogel contact lens formulation will result in clinically acceptable silicone hydrogel contact lenses. Achieving a successful fit, an acceptable level of comfort, an acceptable handling experience, and an acceptable improvement in vision is impacted by various changes in lens chemistry, lens design, and manufacturing processes. For example, changing the formulation of a silicone hydrogel contact lens can alter the oxygen permeability, the water content, the lens surface wettability, and mechanical properties such as modulus, tensile strength, and elasticity. Thus, it is unpredictable as to what combination of chemicals in the formulation will result in desired lens properties.
  • a suitable silicone hydrogel contact lens formulation can be formed using a reaction mixture comprising a silicone component and a silicone-free component.
  • the silicone component comprises, and preferably consists essentially of, two compounds, Formula 1 : wherein Ri is selected from either hydrogen or a methyl group; R 2 is selected from either hydrogen or a C1.4 hydrocarbon group; m represents an integer of from 0 to 10; n represents an integer of from 4 to 100; a and b represent integers of 1 or more; a+b is from 20 to 500; b/(a+b) is from 0.01 to 0.22, and the configuration of siloxane units includes a random configuration; and [0006] Formula 2: where n is an integer from 10 to 25.
  • the compound of Formula 1 and the compound of Formula 2 are at a weight ratio of from 50:50 to 80:20.
  • the weight ratio of the compound of Formula 1 to the compound of Formula 2 is 53:47 to 77:23.
  • Ri is selected from either hydrogen or a methyl group
  • R 2 is selected from either hydrogen or a C1.4 hydrocarbon group
  • m is 0
  • n represents an integer of from 4 to 15
  • a represents an integer from 50 to 250
  • b represents an integer from 5 to 50
  • the configuration of siloxane units includes a random configuration, wherein the ratio of a:b is from 5:1 to 30:1 , preferably 10:1 to 20:1.
  • the silicone component additionally comprises an additional silicone compound of Formula 3: wherein m represents an integer of from 3 to 12, n represents an integer from 1 to 10, R 1 is selected from an alkyl group having from 1 to 4 carbon atoms, R 2 is either a hydrogen atom or a methyl group, and R 3 is either a hydrogen atom or a methyl group.
  • n 1
  • R 1 is a butyl group
  • R 2 is H
  • R 3 is a methyl group
  • the silicone component consists essentially of Formula 1 , Formula 2 and Formula 3.
  • the silicone-free component comprises an N-vinyl amide component and a methacrylate component.
  • the methacrylate component comprises, preferably consists essentially of, and more preferably consists of hydroxybutyl methacrylate (HOB) and isobornyl methacrylate (IBM). It is critical that the HOB and IBM are present in the formulation at a ratio from 60:40 to 90:10. In a preferred embodiment, the weight ratio of HOB to IBM is from 70:30 to 90:10. In a particularly preferred embodiment, the weight ratio of HOB to IBM is from 85:15 to 90:10, more preferably the ratio is about 88:12. In another embodiment, the weight ratio of HOB to IBM is preferably from 75:25 to 80:20, more preferably about 77:23.
  • HOB hydroxybutyl methacrylate
  • IBM isobornyl methacrylate
  • the N-vinyl amide component comprises N-vinyl N-methyl acetamide (VMA).
  • the N-vinyl amide component also comprises N-vinyl pyrrolidone (NVP).
  • NVP N-vinyl pyrrolidone
  • the ratio of NVP to VMA is preferably from 70:30 to 30:70.
  • the N-vinyl amide component consists essentially of and more preferably consists of NVP and VMA.
  • the weight ratio of the compound of Formula 1 to the compound of Formula 2 is from 50:50 to 75:25, preferably from 65:35 to 70:30; [0021] In a second aspect of the present invention, the compound of Formula 2 is present in an amount of at least 12 weight percent;
  • the compound of Formula 1 is present in an amount of less than 38 weight percent
  • the weight ratio of the compound of Formula 2 to the total of the methacrylate component is greater than 0.9:1 ;
  • the weight ratio of compound of Formula 1 to the compound of Formula 2 is less than 3:1 ;
  • the total amount of mono(meth)acrylate compounds in the composition is greater than 26 weight percent.
  • One or more of these aspects can be combined. It has been identified that by restricting the range of components as defined in one or more of these aspects, the tensile strength of the resultant lens can be reduced and the lens thereby improved, without negatively impacting on the other lens properties.
  • the contact lens formulation comprises a silicone component which consists essentially of Formula 1 and Formula 2, wherein the ratio of Formula 1 to Formula 2 is from 53:47 to 57:43.
  • the N-vinyl amide component consists essentially of NVP and VMA, wherein the ratio of NVP:VMA is from 68:32 to 72:28.
  • the methacrylate component consists essentially of HOB and IBM, wherein the ratio of HOB to IBM is from 85:15 to 90:10. It is preferred that the silicone component is from 45 to 55 weight percent of the formulation. It is further preferred that the methacrylate component is from 10 to 20 weight percent of the formulation. It is yet further preferred that the N-vinyl amide component is from 30 to 40 weight percent of the formulation.
  • the contact lens formulation comprises a silicone component which consists essentially of Formula 1 and Formula 2, wherein the ratio of Formula 1 to Formula 2 is from 73:27 to 77:23.
  • the N-vinyl amide component consists essentially of NVP and VMA, wherein the ratio of NVP:VMA is from 32:68 to 28:72.
  • the methacrylate component consists essentially of HOB and IBM, wherein the ratio of HOB to IBM is from 85:15 to 90:10. It is preferred that the silicone component is from 45 to 55 weight percent of the formulation. It is further preferred that the methacrylate component is from 10 to 20 weight percent of the formulation. It is yet further preferred that the N-vinyl amide component is from 30 to 40 weight percent of the formulation.
  • the contact lens formulation comprises a silicone component which consists essentially of Formula 1 , Formula 2 and Formula 3, wherein Formula 3 is present in an amount of less than 0.6 weight percent of the formulation, wherein the ratio of Formula 1 to Formula 2 is from 60:40 to 65:35.
  • the N-vinyl amide component consists essentially of VMA.
  • the methacrylate component consists essentially of HOB and IBM, wherein the ratio of HOB to IBM is from 75:25 to 80:20. It is preferred that the silicone component is from 45 to 55 weight percent of the formulation. It is further preferred that the methacrylate component is from 5 to 15 weight percent of the formulation. It is yet further preferred that the N-vinyl amide component is from 30 to 40 weight percent of the formulation.
  • the formulation further comprises at least one of: a photoinitiator, a thermal initiator; a crosslinking monomer; a UV blocker; and a tinting agent.
  • a silicone hydrogel contact lens comprising the polymerized reaction product of the formulation of any preceding embodiment is disclosed.
  • the silicone hydrogel contact lens may have a tensile strength from 0.4 MPa to 1 .0 MPa.
  • the silicone hydrogel contact lens typically has a tensile strength less than or equal to 1 .0 MPa, and preferably less than or equal to 0.9 MPa.
  • the silicone hydrogel contact lens typically has a tensile strength of at least 0.4 MPa, and more preferably at least 0.5 MPa. In at least some preferred embodiments, the silicone hydrogel contact lens has a tensile strength from 0.5 MPa to 0.9 MPa.
  • the silicone hydrogel contact lens can have a sessile drop contact angle less than 30 degrees, more preferably less than 25 degrees.
  • the silicone hydrogel contact lens can have an equilibrium water content from 45 to 55 wt%.
  • the silicone hydrogel contact lens can have an oxygen permeability of greater than 100 barrers, preferably greater than 110 barrers, more preferably greater than 120 barrers, and especially from 110 to 140 barrers.
  • the silicone hydrogel contact lens can have a Young’s modulus less than or equal to 1.1 MPa, preferably less than or equal to 1.0 MPa.
  • the Young’s modulus is preferably at least 0.3 MPa, more preferably at least 0.5 MPa.
  • a preferred range is from 0.5 MPa to 0.95 MPa.
  • the silicone hydrogel contact lens can have a chord diameter from 13.5 to 15.5 mm and a base curve from 7.5 to 9.5 mm.
  • the skilled person is aware of other suitable chord diameters and base curves.
  • Silicone hydrogel contact lenses are described herein that have good dimensional stability, are ophthalmically-acceptable, and can be manufactured without the use of volatile organic solvents or diluents in the formulations.
  • the silicone hydrogel contact lenses comprise a polymeric lens body that is the reaction product of a polymerizable composition or silicone hydrogel contact lens formulation comprising a silicone component and a silicone-free component.
  • the silicone component comprises, or consists essentially of two compounds, Formula 1 and Formula 2. It is critical that the compound of Formula 1 and the compound of Formula 2 are at a ratio of from 50:50 to 80:20.
  • references herein to ‘at least one’ of a type of ingredient refer to both a) a single ingredient, and b) a combination of two or more ingredients of the same type.
  • references to ‘a total amount’ of a particular component (i.e., a combination of two or more ingredients of the same type) in a polymerizable composition refer to the sum of the amounts of all ingredients of the same type.
  • a “monomer” refers to any molecule capable of reacting with other molecules that are the same or different, to form a polymer or copolymer. Thus, the term encompasses polymerizable pre-polymers and macromers, there being no size-constraint of the monomer unless indicated otherwise.
  • a “siloxane monomer” contains at least one Si — O group, and is typically either “mono-functional” or “multi-functional”, meaning that it has either one polymerizable group or two or more polymerizable groups, respectively.
  • a “non-siloxane monomer” is a monomer that does not contain any Si — O groups.
  • a “silicone component” is a component or portion of the silicone hydrogel contact lens formulation which is composed of all of the siloxane monomers.
  • a “silicone-free component” is a component or portion of the silicone hydrogel contact lens formulation which is composed of all of the non-siloxane monomers
  • N-vinyl amide component is a component or portion of the silicone-free component of the silicone hydrogel contact lens formulation which is composed of at least one non-siloxane monomer that has a vinyl group bound directly to a nitrogen atom.
  • a “methacrylate component” is a component or portion of the silicone-free component of the silicone hydrogel contact lens formulation which is composed of at least one non-siloxane monomer that has a single polymerizable methacrylate group.
  • a “(meth)acrylate-containing monomer” is any non-siloxane monomer that has a single polymerizable (meth)acrylate group (e.g., methyl methacrylate, etc.).
  • a siloxane monomer having at least one polymerizable (meth)acrylate group is referred to herein as a “(meth)acrylate-containing siloxane monomer”.
  • “(Meth)acrylate” covers both methacrylate groups and acrylate groups. Where only methacrylate or acrylate is covered, it will be referred to explicitly.
  • Consists of means that a formulation or component contains only the listed components, compounds, or monomers.
  • Consists essentially of means that a formulation or component contains the listed compounds or monomers but can also contain other monomers or compounds which fall within the definition of that formulation or component such as dimeric or polymeric impurities. These additional monomer or compounds can be present in an amount which does not have an impact on the final lens formulation. Additional monomers or reactive entities can be present in an amount of less than 5%, 2%, 1 %, 0.5% or 0.1 % based on the total amount of the specific formulation or component.
  • a “polymerizable composition” is a composition comprising polymerizable ingredients, where the composition has not yet been subjected to conditions that result in polymerization of the polymerizable ingredients.
  • the present silicone hydrogel contact lens formulations are considered polymerizable compositions.
  • the term “molecular weight”, as used herein, refers to the absolute number average molecular weight Mn (in units of Daltons (Da) or g/mol) of the monomer.
  • the number average molecular weight is typically determined using GPC, using polystyrene standards.
  • the number average molecular weight may be determined by identification of the number average molecular weight on a technical data sheet or specification sheet provided by a chemical supplier to a contact lens manufacturer.
  • a value is given for repeat groups in a structural formula, such as Formula 1 , Formula 2 or Formula 3 it is an average value. The skilled person would understand that a complex molecule of this kind contains a mixture of components.
  • total formulation or “total contact lens formulation” refers to all formulation ingredients excluding diluents and/or solvents that are not incorporated into the final polymeric contact lens material. It can be understood that when a weight percent of an ingredient of the total formulation is provided, it refers to the weight percent of that ingredient based on the total weight of the formulation.
  • ratio refers to weight ratio.
  • weight ratio refers to the ratio between the weight of a first component and the weight of a second component in the formulation.
  • a silicone hydrogel contact lens formulation comprising a silicone component; and a silicone-free component is disclosed herein.
  • the silicone component comprises, or consists essentially of, or in some embodiments consists of, a bi-functional (meth)acrylate-containing siloxane monomer and a mono-functional methacrylate-containing siloxane monomer.
  • the bi-functional (meth)acrylate-containing siloxane monomer is represented by Formula 1 : wherein Ri is selected from either hydrogen or a methyl group; R 2 is selected from either hydrogen or a C1.4 hydrocarbon group; m represents an integer of from 0 to 10; n represents an integer of from 4 to 100; a and b represent integers of 1 or more; a+b is from 20-500; b/(a+b) is from 0.01-0.22, and the configuration of siloxane units includes a random configuration.
  • the bi-functional (meth)acrylate-containing siloxane monomer of Formula 1 can have an average molecular weight Mw of at least 8,000, 10,000, 12,000 or 15,000 Da.
  • the bifunctional (meth)acrylate-containing siloxane monomer of Formula 1 can have an average molecular weight Mw of less than 25,000, 20,000 12,000, 11 ,000, 10,000 or 9,000 Da.
  • the bi-functional (meth)acrylate-containing siloxane monomer has an average molecular weight Mw of from 8,000 to 20,000 Da.
  • the bi- functional (meth)acrylate-containing siloxane monomer of Formula 1 has an average molecular weight Mw of from 8,000 to 11 ,000 Da.
  • the bi-functional (meth)acrylate-containing siloxane monomer of Formula 1 has an average molecular weight Mw of from 15,000 to 20,000 Da.
  • Ri is selected from either hydrogen or a methyl group
  • R 2 is selected from either hydrogen or a C1-4 hydrocarbon group
  • m is 0
  • n represents an integer of from 4 to 15
  • a represents an integer from 50 to 250
  • b represents an integer from 5 to 50
  • the configuration of siloxane units includes a random configuration, wherein the ratio of a: b is from 5:1 to 30:1 , preferably 10:1 to 20:1.
  • Ri is a methyl group. It is preferred that R 2 is H or a methyl group, and more preferably a methyl group. It is additionally preferred that m is 0. It is preferred that n is from 6 to 9.
  • a is from 60 to 100, more preferably from 70 to 80, and b is from 4 to 8, more preferably from 5 to 8. It is further preferred that Ri is methyl, R 2 is methyl, m is 0 and n is from 7 to 8.
  • a particularly preferred bi-functional (meth)acrylate-containing siloxane monomer has a CAS Registry Number of: 1216820-69-7.
  • a is from 140 to 220, more preferably from 150 to 200, and b is from 8 to 15, more preferably from 9 to 13. It is further preferred that Ri is methyl, R 2 is methyl, m is 0 and n is from 7 to 8.
  • the mono-functional methacrylate-containing siloxane monomer is represented by Formula 2: where n is an integer from about 10 to 25, preferably from 13 to 18.
  • the mono-functional methacrylate-containing siloxane monomer of Formula 2 has an average molecular weight of less than 2,000, preferably less than 1 ,800 Da, and greater than 800, preferably greater than 1 ,000 Da.
  • the mono-functional methacrylate-containing siloxane monomer may have an average molecular weight of from 1 ,000 to 1 ,800 Da.
  • the mono-functional methacrylate-containing siloxane monomer has a CAS registry number of 697234-76-7.
  • Siloxane monomers of Formula 2 are described in US. Pat. No. 6,310,169 (incorporated herein by reference).
  • the compound of Formula 1 and the compound of Formula 2 are at a weight ratio of from 50:50 to 80:20.
  • the weight ratio of the compound of Formula 1 to the compound of Formula 2 is from 53:47 to 77:23.
  • the weight ratio is from 52:48 to 58:42.
  • the weight ratio is from 60:40 to 65:35.
  • the weight ratio is from 70:30 to 77:23.
  • the weight ratio is about 55:45, about 63:37 or about 75:25.
  • the silicone component comprises an additional silicone compound, which is a mono-functional (meth)acrylate-containing siloxane monomer of Formula 3: wherein m represents an integer of from 3 to 12, n represents an integer from 1 to 10, R 1 is selected from an alkyl group having from 1 to 4 carbon atoms, and each of R 2 and R 3 of Formula 3 is independently selected from a hydrogen atom or a methyl group.
  • m represents an integer of from 3 to 12
  • n represents an integer from 1 to 10
  • R 1 is selected from an alkyl group having from 1 to 4 carbon atoms
  • each of R 2 and R 3 of Formula 3 is independently selected from a hydrogen atom or a methyl group.
  • n 1 . It is further preferred that R 1 is a butyl group, R 2 is H, and R 3 is a methyl group.
  • the silicone component consists essentially, preferably consists of Formula 1 , Formula 2 and Formula 3.
  • the weight percent of the silicone component is greater than 48%, 48.5%, or 49%. In some embodiments the weight percent of the silicone component is less than 53%, 52.5%, 52%, 51.5%, 51%, or 50.5%. In some embodiments any one of the lower limits of the weight percent of the silicone component is combined with any one of the upper limits of the weight percent of the silicone component.
  • the silicone component can be present in the formulation from 48% (wt/wt) to 53% (wt/wt), preferably from 48% to 51 %.
  • the amount of the compound of Formula 2 is greater than 12 weight percent of the total composition. It is further preferred that the amount of the compound of Formula 2 is less than 25 weight percent.
  • the compound of Formula 2 can be present in the formulation from 12 to 25 % (wt/wt).
  • the amount of the compound of Formula 1 is less than 38 weight percent. It is further preferred that the amount of the compound of Formula 1 is greater than 26 weight percent.
  • the compound of Formula 1 can be present in the formulation from 26 to 38 % (wt/wt).
  • the amount of the compound of Formula 2 is greater than 12 weight percent and the amount of the compound of Formula 1 is less than 38 weight percent.
  • the silicone component of the present formulations is free of a hydroxy-functionalized siloxane compound, is free of TRIS, or is free of both.
  • the silicone-free component comprises an N-vinyl amide component (c); and a methacrylate component (d).
  • the N-vinyl amide component comprises N-vinyl N-methyl acetamide (VMA).
  • the N-vinyl amide component optionally further comprises N-vinyl pyrrolidone (NVP). It is further preferred that the N-vinyl amide component consists essentially of, and preferably consists of NVP and VMA.
  • the ratio of NVP to VMA is from 70:30 to 30:70. In some embodiments the ratio is about 70:30. In some embodiments the ratio is about 30:70.
  • the polymerizable composition has a weight ratio of total amount of N-vinyl amide component to total amount of (meth)acrylate-containing siloxane monomer (i.e. the mono- and bi-functional (meth)acrylate-containing siloxane monomers) of from about 40:60 to 45:55. It is further preferred that the ratio is from 41 :59 to 42:58.
  • the weight percent of the N-vinyl amide component is greater than 34%, or 34.5%. In some embodiments the weight percent of the N-vinyl amide component is less than 40%, 39%, 37% or 36.5%. In some embodiments any one of the lower limits of the weight percent of the N-vinyl amide component is combined with any one of the upper limits of the weight percent of the N-vinyl amide component. In some embodiments the weight percent of the N-vinyl amide component is between 34.5% and 35.5%.
  • the N-vinyl amide component consists essentially of, and preferably consists of VMA.
  • the polymerizable composition has a weight ratio of total amount of N-vinyl amide component to total amount of (meth)acrylate- containing siloxane monomer (i.e., the mono- and bi-functional (meth)acrylate-containing siloxane monomers) of from about 40:60 to 45:55. It is further preferred that the ratio is from 44:56 to 45:55.
  • the weight percent of the N-vinyl amide component is greater than 35%, or 38%.
  • the weight percent of the N-vinyl amide component is less than 40% or 39%.
  • any one of the lower limits of the weight percent of the N-vinyl amide component is combined with any one of the upper limits of the weight percent of the N-vinyl amide component.
  • the weight percent of the N-vinyl amide component is between 38% and 39%.
  • the total amount of the compound of Formula 2 and the N-vinyl amide component is at least 47 weight percent, preferably at least 50 weight percent.
  • the total amount of the compound of Formula 2 and the N-vinyl amide component is less than 70 weight percent, preferably less than 60 weight percent.
  • the methacrylate component (d) comprises, and in some embodiments consists essentially of, and in some embodiments consists of, hydroxybutyl methacrylate (HOB) and isobornyl methacrylate (IBM), wherein the hydroxybutyl methacrylate and isobornyl methacrylate are present in the formulation at a weight ratio from 60:40 to 90:10.
  • the ratio of HOB to IBM is greater than 65:35, 70:30, 75:25, 80:20, 85:15, or 87:13.
  • the ratio of HOB to IBM is less than 90:10, 89.5:10.5, 89:11 , or 88.5:11 .5.
  • any one of the lower limits of ratio of HOB to IBM is combined with any one of the upper limits of the ratio of HOB to IBM.
  • the ratio of HOB to IBM is between 85:15 and 90:10 or is about 88:12.
  • silicone-free methacrylate-containing monomers are known in the field and can be present in the contact lens formulation.
  • exemplary silicone-free methacrylate-containing monomers include methyl methacrylate (MMA), tert butyl methacrylate (tBMA), 2-hydroxyethyl methacrylate (HEMA), ethylene glycol methyl ether methacrylate (EGMA), and combinations thereof.
  • a preferred additional silicone-free methacrylate-containing monomer is methyl methacrylate (MMA).
  • these additional methacrylate-containing monomers are present in a total amount of less than 5%, more preferably less than 3% by weight, yet more preferably less than 1 % by weight of the contact lens formulation and even more preferably in the minor amounts as defined above where the methacrylate component consists essentially of HOB and IBM. It is particularly preferred that there are no other methacrylate-containing monomers.
  • the ratio of HOB to IBM is from 60:40 to 65:35 or where the total amount of IBM is greater than 5 weight percent, it is preferred in one embodiment that the ratio of the compound of Formula 1 to the compound of Formula 2 is less than or equal to 3:1 , preferably from 50:50 to 75:25, more preferably from 65:35 to 70:30.
  • the amount of the compound of Formula 2 is greater than 12 weight percent of the total composition. This is particularly the case where the ratio of HOB to IBM is from 60:40 to 65:35 or where the total amount of IBM is greater than 5 weight percent. It is further preferred that the amount of the compound of Formula 2 is less than 25 weight percent.
  • the amount of the compound of Formula 1 is less than 38 weight percent. This is particularly the case where the ratio of HOB to IBM is from 60:40 to 65:35 or where the total amount of IBM is greater than 5 weight percent. It is further preferred that the amount of the compound of Formula 1 is greater than 26 weight percent.
  • the amount of the compound of Formula 2 is greater than 12 weight percent and the amount of the compound of Formula 1 is less than 38 weight percent.
  • the polymerizable composition may have a weight ratio of compound of Formula 2 to total amount of non-siloxane methacrylate-containing monomer of greater than 0.9: 1 , preferably greater than 1 :1. This is particularly the case where the ratio of HOB to IBM is from 60:40 to 65:35 or where the total amount of IBM is greater than 5 weight percent.
  • the total amount of mono-functional methacrylate- containing non-silicone and siloxane monomers collectively is greater than 26 weight percent, and preferably greater than 30 weight percent. This is particularly the case where the ratio of HOB to IBM is from 60:40 to 65:35 or where the total amount of IBM is greater than 5 weight percent.
  • the formulation further comprises one or more additional components which are common in contact lens formulations.
  • additional components include a photoinitiator, a thermal initiator, a cross-linking agent, UV blockers and a tinting agent.
  • the polymerizable composition may additionally comprise at least one non- siloxane cross-linking agent.
  • a “cross-linking agent” is any compound having a molecular weight of less than about 2,000 Da. with two or more ethylenically unsaturated groups.
  • a cross-linking agent can react with functional groups on two or more polymer chains so as to bridge one polymer to another.
  • TAIC is particularly preferred as the cross-linker in the formulations of the present invention.
  • the cross-linker is preferably used in an amount of from 0.03 to 0.2 weight percent of the contact lens formulation.
  • the composition additionally can comprise one or more tinting agents.
  • Preferred tinting agents are reactive tinting agents and particularly tinting agents identified as “Reactive Blue” dyes.
  • composition can additionally comprise one or more UV blockers.
  • Contact lenses can be made from the polymerizable compositions described herein using curing and other processing methods known in the field, such as cast molding, spin casting, injection molding, forming a polymerized rod that is subsequently lathed, etc.
  • the polymerizable composition is cast molded between molds formed of a thermoplastic polymer.
  • the thermoplastic polymer is typically a non-polar material, such as polypropylene, but polar mold materials, such as ethylene vinyl alcohol, are also used in the field.
  • a first mold member defining the front surface of the contact lens referred to as a “female mold member”
  • a second mold member defining the back (i.e. eyecontacting) surface of the contact lens referred to as the “male mold member” is coupled to the female mold member to form a mold assembly having a lens-shaped cavity with the amount of polymerizable composition therebetween
  • the polymerizable composition within the contact lens mold assembly is polymerized using any suitable curing method. Typically, the polymerizable composition is exposed to polymerizing amounts of heat or ultraviolet light (UV). In the case of UV-curing, also referred to as photopolymerization, the polymerizable composition typically comprises a photoinitiator such as benzoin methyl ether, 1 -hydroxycyclohexylphenyl ketone, Darocur or Irgacur (available from Ciba Specialty Chemicals). Photopolymerization methods for contact lenses are described in U.S. Pat. No. 5,760,100 incorporated herein by reference.
  • the polymerizable composition typically comprises a thermal initiator.
  • thermal initiators include 2,2'-azobis(2,4- dimethylpentanenitrile) (VAZO-52), 2,2'-Azobis(2-methylpropanenitrile) (VAZO-64), and 1 ,1'-azo bis(cyanocyclohexane) (VAZO-88).
  • the contact lens mold assemblies containing the contact lens formulations are cured by exposing the contact lens mold assemblies to heat or UV light for a time ranging from about 1 hour to about 5 hours. Additional thermal polymerization methods for contact lenses are described in US Publ. no. 2007/0296914 and U.S. Pat. No. 7,854,866, incorporated herein by reference.
  • the polymerized material between the mold members of the mold assembly has the shape of a contact lens, and is referred to herein as a “polymeric lens body”.
  • the male and female mold members are demolded, i.e. separated, and the polymeric lens body is removed, i.e. delensed, from the mold member to which it is adhered.
  • demolding and delensing are referred to as demolding and delensing, respectively, and a variety of such methods are known to those of ordinary skill in the field.
  • the demolding and delensing processes can comprise a single process step, such as when the molds are separated using a liquid which also removes the polymeric lens body from the mold.
  • the polymeric lens body typically remains on one of the mold members and is delensed in a subsequent process step.
  • Delensing can also be a wet or dry process.
  • delensing is carried out by a “float off’ method in which the mold member to which a polymeric lens body is adhered is immersed in water. The water may optionally be heated (e.g. up to about 100° C.). Typically, the polymeric lens bodies float off of the mold members in about ten minutes.
  • Dry delensing can be carried out manually, for example using tweezers to remove the polymeric lens bodies from the mold member, or they can be removed using an automated mechanical process, such as described in U.S. Pat. No. 7,811 ,483 (incorporated herein by reference). Additional demolding and delensing methods for silicone hydrogel contact lenses are described in US Publ No. 2007/0035049 (incorporated herein by reference).
  • the polymeric lens body is washed to remove unreacted or partially reacted ingredients from the polymeric lens body and to hydrate the polymeric lens body.
  • the contact lenses can be exposed to organic solvents, such as ethanol, isopropyl alcohol, industrial methylated spirts, and the like, or water, or mixtures thereof. Exemplary washing methods are described in US Pat. Publ. No. 2007/0296914 (incorporated herein by reference) and in Example 1 below.
  • the hydrated polymeric lens body is typically placed into a blister package, glass vial, or other appropriate container, all referred to herein as “packages.”
  • a packaging solution is also added to the container, which is typically a buffered saline solution such as phosphate- or borate-buffered saline.
  • the packaging solution may optionally contain additional ingredients such as a comfort agent, a hydrophilic polymer, a surfactant or other additive that prevents the lens from sticking to the container, etc.
  • the package is sealed, and the sealed polymeric lens body is sterilized by autoclaving.
  • the final product is a sterile, packaged ophthalmically-acceptable contact lens.
  • the contact lens may be characterized by one or more of the following properties: contact angle, oxygen permeability, tensile strength, Young’s modulus, and equilibrium water content, as detailed below.
  • the contact lens may have a contact angle of less than about 30°, or 25°, where the contact angle is the static advancing contact angle as determined using a sessile drop method.
  • contact lenses to be tested are soaked in phosphate buffered solution (PBS) for at least 12 hours.
  • PBS phosphate buffered solution
  • the lenses are removed from the PBS and shaken to remove excess water. A 4 mm diameter section of each lens is cut with a lens cutter.
  • the surface of the contact lens section to be tested is blotted dried by placing it face down on a microscope lens wipe and gently dragging the lens section across the wipe using rubber tipped tweezers until no liquid is observed absorbing into the wipe.
  • the lens section is placed on a microscope slide, ensuring that it lies flat with the blotted surface facing upwards.
  • the microscope slide is placed on the sample stage so that the longer side of the lens section is perpendicular to the camera.
  • the syringe is moved to fit in the viewing screen and the image is adjusted until a maximum is reached in the median window.
  • the water is dispensed onto the lens.
  • the image of the drop is captured.
  • the average contact angle measurement of 5 lens sections is taken to be the contact angle for the particular surface (i.e. posterior or anterior) of the contact lens.
  • the Dk values provided in the Examples below were determined using a Rehder 201T Oxygen Permometer/polarographic cell following the polarographic method described in ISO18369-4:2017 section 4.4.3.
  • the contact lens may have a Young’s modulus (i.e. tensile modulus) of at least 0.3 MPa or 0.5 MPa, to 0.95 MPa, 1 .0 MPa or 1 .1 MPa. In preferred embodiments, the contact lens has a Young's modulus from 0.3 MPa to 1 .1 MPa, and preferably from 0.5 to 0.95 MPa.
  • Young’s modulus i.e. tensile modulus
  • the contact lenses have a tensile strength of less than or equal to 1.0 MPa, preferably less than or equal to 0.9 MPa.
  • the contact lens typically has a tensile strength of at least 0.4 MPa, more preferably at least 0.5 MPa.
  • Preferred embodiments of the present contact lenses have a tensile strength from 0.5 MPa to 0.9 MPa.
  • the modulus, elongation, and tensile strength values reported herein were determined using an Instron Model 3342, 3343, or 5944 mechanical testing system (Instron Corporation, Norwood, Mass., USA) and Bluehill Materials Testing Software, using a custom- built rectangular contact lens cutting die with 4 mm spacing to prepare the rectangular sample strip.
  • the modulus was determined inside a chamber having a relative humidity of least 70%.
  • a lens was soaked in phosphate buffered solution (PBS) for at least 10 minutes prior to testing. While holding the lens concave side up, a central strip of the lens was cut using the cutting die.
  • the thickness of the strip was determined using a calibrated gauge (Rehder electronic thickness gauge, Rehder Development Company, Castro Valley, Calif., USA).
  • the strip was loaded into the grips of the calibrated Instron apparatus, with the strip fitting over at least 75% of the grip surface of each grip.
  • a test method designed to determine the maximum load (N), the tensile strength (MPa), the strain at maximum load (% elongation) and the mean and standard deviation of the tensile modulus (MPa) was run, and the results were recorded.
  • the contact lens may have an equilibrium water content (EWC) of at least about 30 wt. %, 40 wt. % or 45 wt. % and up to about 50 wt%, 55 wt%, 60 wt. % or 70 wt. %.
  • the contact lens may have an EWC from 40 to 60 wt%.
  • EWC equilibrium water content
  • excess surface water is wiped off the lens and the lens is weighed to obtain the hydrated weight.
  • the lens is dried in an oven at 105° C, and weighed.
  • the weight difference is determined by subtracting the weight of the dry lens from the weight of the hydrated lens.
  • the wt. % EWC of the lens (weight difference/hydrated weight)x100.
  • the contact angle is ⁇ 30° and the equilibrium water content is most preferably at least 45 wt. % and up to 55 wt%.
  • the exemplary components of the polymerizable composition disclosed herein are typically combined in embodiments of the invention.
  • the polymerizable composition of the invention advantageously includes the exemplary mono-functional (meth)acrylate-containing siloxane monomers disclosed herein in combination with the exemplary bi-functional (meth)acrylate-containing siloxane monomers disclosed herein and in combination with the exemplary N-vinyl amide components disclosed herein and in combination with the exemplary (meth)acrylate components disclosed herein.
  • the lenses were either cured using ultraviolet light for about 1 hour (Examples 1 and 2 and Comparative Examples) or heat for about 5 hours (Example 3).
  • the skilled person is aware of suitable methods for curing contact lens formulations.
  • the cured polymers were removed from the contact lens molds and washed to remove unreacted materials by contacting them with organic solvent, water, or combinations thereof, and then the washed contact lenses were placed in a package and sterilized in an autoclave to provide a sterilized packaged contact lens.
  • the contact lenses of all Examples and Comparative Examples were transparent and flexible, and also had good water wettability.
  • the particular selection of selection of the formulation of the present invention can cause such a significant reduction in the tensile strength of the resulting lens.
  • the lenses of the present invention retain the other advantageous features seen in prior art lenses formed using the same combination of siloxane monomers, such as high Dk and good sessile drop contact angle.

Landscapes

  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Eyeglasses (AREA)
  • Macromonomer-Based Addition Polymer (AREA)

Abstract

L'invention concerne des formulations de lentilles de contact en hydrogel de silicone. Les formulations ont un composant silicone et un composant sans silicone. Le composant silicone comprend deux ou trois composés représentés par la formule 1, la formule 2 ou la formule 3. Le composant sans silicone comprend un composant méthacrylate et un composant N-vinyl amide. Le composant méthacrylate comprend du méthacrylate d'hydroxybutyle (HOB) et du méthacrylate d'isobornyle (IBM). Le composant N-vinyl amide comprend du N-vinyl N-méthyl acétamide. Lorsque les composés de formule 1 et de formule 2 sont présents dans les formulations dans un rapport spécifié l'un par rapport à l'autre, la fourniture du HOB et de l'IBM dans des quantités spécifiques pour obtenir les rapports spécifiés conduit à des lentilles de contact en hydrogel de silicone souhaitées. L'invention concerne également les lentilles de contact en hydrogel de silicone.
PCT/GB2024/051767 2023-07-11 2024-07-05 Formulation de lentilles de contact et lentille de contact Pending WO2025012621A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US202363526045P 2023-07-11 2023-07-11
US63/526,045 2023-07-11
GBGB2311167.7A GB202311167D0 (en) 2023-07-20 2023-07-20 Contact lens formulation and contact lens
GB2311167.7 2023-07-20

Publications (1)

Publication Number Publication Date
WO2025012621A1 true WO2025012621A1 (fr) 2025-01-16

Family

ID=91954115

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB2024/051767 Pending WO2025012621A1 (fr) 2023-07-11 2024-07-05 Formulation de lentilles de contact et lentille de contact

Country Status (1)

Country Link
WO (1) WO2025012621A1 (fr)

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5760100A (en) 1994-09-06 1998-06-02 Ciba Vision Corporation Extended wear ophthalmic lens
US6310169B1 (en) 1999-03-08 2001-10-30 Chisso Corporation Polymerizable terminal group-containing polyorganosiloxane and production process for the same
US20070035049A1 (en) 2005-08-09 2007-02-15 Coopervision Inc. Systems and methods for removing lenses from lens molds
US20070296914A1 (en) 2006-06-15 2007-12-27 Ye Hong Wettable Silicone Hydrogel Contact Lenses and Related Compositions and Methods
US7811483B2 (en) 2006-06-01 2010-10-12 Coopervision International Holding Company, Lp Delensing of ophthalmic lenses using gas
US7854866B2 (en) 2007-05-18 2010-12-21 Coopervision International Holding Company, Lp Thermal curing methods and systems for forming contact lenses
US8129442B2 (en) 2008-02-08 2012-03-06 Coopervision International Holding Company, Lp Hydrophilic polysiloxane macromonomer, and production and use of the same
US20120220689A1 (en) * 2011-02-28 2012-08-30 Coopervision International Holding Company, Lp Silicone Hydrogel Contact Lenses
JP6023589B2 (ja) * 2009-10-01 2016-11-09 クーパーヴィジョン インターナショナル ホウルディング カンパニー リミテッド パートナーシップ シリコーンヒドロゲルコンタクトレンズおよびシリコーンヒドロゲルコンタクトレンズの製造方法

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5760100A (en) 1994-09-06 1998-06-02 Ciba Vision Corporation Extended wear ophthalmic lens
US5760100B1 (en) 1994-09-06 2000-11-14 Ciba Vision Corp Extended wear ophthalmic lens
US6310169B1 (en) 1999-03-08 2001-10-30 Chisso Corporation Polymerizable terminal group-containing polyorganosiloxane and production process for the same
US20070035049A1 (en) 2005-08-09 2007-02-15 Coopervision Inc. Systems and methods for removing lenses from lens molds
US7811483B2 (en) 2006-06-01 2010-10-12 Coopervision International Holding Company, Lp Delensing of ophthalmic lenses using gas
US20070296914A1 (en) 2006-06-15 2007-12-27 Ye Hong Wettable Silicone Hydrogel Contact Lenses and Related Compositions and Methods
US7854866B2 (en) 2007-05-18 2010-12-21 Coopervision International Holding Company, Lp Thermal curing methods and systems for forming contact lenses
US8129442B2 (en) 2008-02-08 2012-03-06 Coopervision International Holding Company, Lp Hydrophilic polysiloxane macromonomer, and production and use of the same
JP6023589B2 (ja) * 2009-10-01 2016-11-09 クーパーヴィジョン インターナショナル ホウルディング カンパニー リミテッド パートナーシップ シリコーンヒドロゲルコンタクトレンズおよびシリコーンヒドロゲルコンタクトレンズの製造方法
US20120220689A1 (en) * 2011-02-28 2012-08-30 Coopervision International Holding Company, Lp Silicone Hydrogel Contact Lenses

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
no. 697234-76-7

Similar Documents

Publication Publication Date Title
AU2012223594B2 (en) Silicone hydrogel contact lenses
EP2681614B1 (fr) Lentilles de contact en hydrogel de silicone mouillables
EP2492718B1 (fr) Lentilles de contact à hydrogel en silicone
WO2007146312A2 (fr) Lentilles de contact en hydrogel de silicone mouillable et compositions et procédés associés
GB2623152A (en) Contact lens formulation and contact lens
WO2025012621A1 (fr) Formulation de lentilles de contact et lentille de contact
WO2025012623A2 (fr) Formulation pour lentille de contact et lentille de contact
WO2025012624A2 (fr) Formulation pour lentille de contact et lentille de contact
WO2025012622A2 (fr) Formulation de lentilles de contact et lentille de contact
GB2633454A (en) Contact lens formulation and contact lens
GB2623153A (en) Contact lens formulation and contact lens
GB2633455A (en) Contact lens formulation and contact lens
GB2633456A (en) Contact lens formulation and contact lens
EP1955842A1 (fr) Lentilles de contact à hydrogel en silicone mouillable, et compositions et procédés associés
GB2633452A (en) Contact lens formulation and contact lens
GB2700031A (en) Contact lens formulation and contact lens
GB2629236A (en) Contact Lens Formulation and Contact Lens
GB2629223A (en) Tinted silicone hydrogel contact lens formulations and contact lenses
HK1189275B (en) Silicone hydrogel contact lenses
HK1187693B (en) Wettable silicone hydrogel contact lenses
HK1194091B (en) Silicone hydrogel contact lenses
HK1214368A1 (zh) 含伯胺的硅酮水凝胶隐形眼镜片与相关组合物和方法

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 24743463

Country of ref document: EP

Kind code of ref document: A1