JP5982684B2 - Wettable silicone hydrogel contact lenses and related compositions and methods - Google Patents

Description

[Cross-reference for related applications]
This application includes US Patent Application No. 60 / 804,911 filed on June 15, 2006; US Patent Application No. 60 / 887,513 filed on January 31, 2007; and US Patent Application filed on March 13, 2007 Claim the benefit of 60 / 894,609 priority. The entire contents of these applications are incorporated herein by reference.
(Field of the Invention)
The present invention relates to silicone hydrogel ophthalmic devices and related compositions and methods. More particularly, the present invention relates to wettable molded silicone hydrogel contact lenses and related compositions and methods.

Silicone hydrogel contact lenses have become popular because wearers can wear them for a longer time than non-silicone hydrogel contact lenses. Depending on the individual lens, for example, one day, one week, two weeks, or one month silicone hydrogel contact lenses can be worn, or for one day, one week, two weeks, or one month A silicone hydrogel contact lens can be formulated. The benefits for lens wearers associated with silicone hydrogel contact lenses may be due, at least in part, to the combination of the hydrophilic component and the hydrophobic properties of the silicon-containing polymer material of the contact lens.
Non-silicone hydrogel contact lenses, such as 2-hydroxyethyl methacrylate (HEMA) based hydrogel contact lenses, are often manufactured in non-polar resin contact lens molds, such as polyolefin-based resin contact lens molds. In other words, a lens precursor composition for a non-silicone hydrogel contact lens is polymerized in a non-polar resin contact lens mold to produce a HEMA-based polymer lens product or a polymerized lens product. Due to the hydrophilic nature of the polymer component of HEMA-based contact lenses, HEMA-based contact lenses are compatible with the eye and are acceptable to the eye even though they are produced using a non-polar resin mold Has surface wettability.
However, existing silicone hydrogel contact lenses obtained from nonpolar resin molds have a hydrophobic lens surface. In other words, the surface of such a silicone hydrogel contact lens has low wettability and is therefore not compatible or acceptable to the eye. For example, such silicone hydrogel contact lenses can be associated with increased fat deposition, protein deposition, and irritation to lens wearers. Surface treatment or surface modification is used on the surface of such silicone hydrogel contact lenses or lens products to increase the hydrophilicity and wettability of the lens surface. Examples of surface treatments for silicone hydrogel lenses include coating the surface of the lens, adsorption of chemical species on the surface of the lens, changing the chemical nature of chemical groups on the surface of the lens or changing the electrostatic charge. Disclosed is a surface treatment comprising coating a polymerized lens surface with a plasma gas or treating the mold prior to forming a polymerized lens using a plasma gas on the surface of a contact lens mold. Yes. Contact lens surface treatment requires more machinery and time to produce contact lenses than manufacturing methods that do not use surface treatment or modification. Furthermore, surface treated silicone hydrogel contact lenses may exhibit low surface wettability when wearing the lens and / or when handled by a lens wearer. For example, increasing the handling of surface treated lenses can cause the hydrophilic surface to decompose or wear.

  An alternative approach to increasing the wettability and ophthalmic compatibility of silicone hydrogel lenses is a silicone hydrogel contact lens precursor composition in the presence of a different composition containing a polymer wetting agent such as polyvinylpyrrolidone (PVP). ) Is polymerized. This type of lens can be interpreted as a “silicone hydrogel contact lens with a polymer internal wetting agent”. Further, these lenses can be interpreted as constituting an “interpenetrating polymer network (IPN)” that includes high molecular weight polymers such as PVP. As will be appreciated by those skilled in the art, an IPN represents a combination of two or more different polymers in network form, with at least one polymer in the presence of the other polymer and any covalent bond between the polymers. Without being synthesized and / or cross-linked. An IPN can be composed of two separate but two types of chains that form a network, proximal or interpenetrating. Examples of IPN include sequential IPN, simultaneous IPN, semi-IPN and homo-IPN. Silicone hydrogel contact lenses containing the polymeric wetting agent IPN avoid the problems associated with surface treatment, but these lenses cannot retain their ophthalmic compatibility, such as long-term surface wettability. For example, because the internal wetting agent is not covalently bonded to other polymerized lens-forming components, the internal wetting agent leaches out of the lens while worn by the lens wearer, thereby surface wettability over time. Can be reduced and the discomfort of the lens wearer can increase.

As an alternative to the use of surface treatment or polymer wetting agent IPN, as described above, using polar resin molds instead of nonpolar resin molds to produce eye-acceptable surface wettable silicone hydrogel contact lenses I know I can. For example, silicone hydrogel contact lenses formed in ethylene-vinyl alcohol or polyvinyl alcohol based molds have desirable surface wettability. An example of a useful polar resin used in the manufacture of contact lens molds for the production of non-surface treated silicone hydrogel contact lenses without the IPN polymer wetting agent is sold by Nippon Gosei Co., Ltd. under the trade name SOARLITE ^TM An ethylene-vinyl alcohol copolymer resin such as an ethylene-vinyl alcohol copolymer resin. In addition to its polarity, SOARLITE ^TM has been described as having the following properties: extremely high mechanical strength, antistatic properties, low shrinkage when used in the molding process, excellent oil and solvent resistance, Small coefficient of thermal expansion and good friction resistance.
While SOARLITE ^™ based molds provide a desirable alternative for producing silicone hydrogel contact lenses that can be adapted to the eye without the use of surface treatments or polymer wetting agents IPN, SOARLITE ^™ molds are polypropylene molds It is more difficult to deform than a non-polar resin mold or is not flexible, and is relatively difficult to process as compared to a non-polar resin mold.
Examples of documents that may be relevant to the manufacture of such silicone hydrogel contact lenses include: U.S. Pat. Nos. 4,121,896; 4,495,313; 4,565,348; 4,640,489; 4,889,664; 4,985,186; 5,094,609; 5,260,000; 5,607,518; 5,760,100; 5,850,107; 5,935,492; 6,099,852; 6,367,929; 6,822,016; 6,867,245; 6,867,245; And US Patent Publication Nos. 20030125498; 20050154080; and 20050191335.

U.S. Pat.No. 4,121,896

In view of the above, it is easier to manufacture than silicone hydrogel lenses obtained from SOARLITE ^TM contact lens molds and requires the use of a polymer wetting agent IPN such as surface treatment or PVP IPN to achieve ophthalmic compatibility. There continues to be a need for eye-compatible silicone hydrogel contact lenses. Existing problems are compatible with eyes such as silicone hydrogel contact lenses with non-polar resin or polyolefin-based contact lens mold parts, with surface wettability compatible with the eye, without the use of surface treatments or polymer wetting agents IPN To obtain a functional silicone hydrogel contact lens.

〔Overview〕
The contact lenses, lens products, compositions, and methods of the present invention attempt to address the needs and problems associated with existing silicone hydrogel contact lenses. Surprisingly, by supplying a relatively large amount of removable material to the pre-extracted polymerized silicone hydrogel contact lens product that is extracted and hydrated to yield a silicone hydrogel contact lens, It has been discovered that compatible silicone hydrogel contact lenses can be obtained. A pre-extracted polymerized silicone hydrogel lens product having at least one removable material, including a removable component, i.e., an extractable material, etc. (at least of the pre-extracted polymerized silicone hydrogel lens product) About 10% by weight of the removable component) can be extracted and hydrated to form a silicone hydrogel contact lens with ophthalmically acceptable surface wettability as described herein. . The lens allows for comfortable wearing in the patient's eyes for a long period of time, for example, at least 1 day, at least 1 week, at least 2 weeks, or about 1 month without the need to remove the lens from the eye It has oxygen permeability, surface wettability, modulus, moisture content, ionoflux, and design.

The silicone hydrogel contact lens includes a lens body having surfaces such as an anterior surface and a posterior surface that are wettable to the eye. The surface wettability of the silicone hydrogel contact lens is related to the amount of removable components present in the polymerized silicone hydrogel contact lens product prior to extraction. The lens body of the present silicone hydrogel contact lens does not require a surface treatment or a polymer wetting agent IPN to obtain an eye-acceptable surface wettability. The lens body of the present silicone hydrogel contact lens does not require the use of a polar resin mold, such as a SOARLITE ^™ based mold, in order to obtain eye-acceptable surface wettability. Furthermore, the lens does not require further machining after a curing or delensing procedure. However, certain embodiments of the present invention may optionally include surface treatment, use of polymer wetting agent IPN, and / or polar resin molds, or post-curing machining or post-lens machining. Will be understood.
One aspect of the present invention relates to a silicone hydrogel contact lens. The silicone hydrogel contact lens includes a lens body having an eye-acceptable surface wettability. In certain embodiments, the lens body can be interpreted as including a silicone hydrogel material and can have a dry weight that does not exceed 90% of the dry weight of the lens body prior to extraction. The dry weight can be interpreted as the weight of the lens body that does not contain a noticeable amount of water or any amount of water. In another specific embodiment, the lens body is a lens body obtained from a polymerized silicone hydrogel contact lens product prior to extraction having a removable component in an amount of at least 10% (w / w). Can be interpreted. In other words, the polymerized silicone hydrogel contact lens product prior to extraction has at least 10% (w / w) removable components. In a further embodiment, the lens body extracts an extractable component from the polymerized silicone hydrogel contact lens product prior to extraction to produce an extracted polymerized silicone hydrogel contact lens product and the extracted The polymerized silicone hydrogel contact lens product can be interpreted to be a lens body made by hydrating to produce a silicone hydrogel contact lens with eye-acceptable surface wettability. The pre-extracted polymerized silicone hydrogel contact lens product has an extractable component content of at least 10% (w / w) of the pre-extracted lens body.

It is a flowchart which shows the process of the manufacturing method of a silicone hydrogel contact lens. 2 is a flowchart showing the composition, lens product, and contact lens of the present invention.

In some embodiments, the pre-extracted polymerized silicone hydrogel contact lens product having a removable component content of at least 10% (w / w) is substantially or completely non-reactive, such as a diluent. There are no additives. For example, such a pre-extracted lens product is obtained from a polymerizable composition free of diluents, compatibilizers, or other non-reactive additives. As used herein, a polymerizable composition without a diluent, compatibilizer, or other non-reactive additive may be referred to as a “bulk formulation” or “bulk composition”. The bulk formulation is a pre-extracted polymerized silicone hydrogel of the present invention that is free of non-reactive additives and has an extractable component content of at least 10% (w / w) of the lens body prior to extraction. A contact lens product can be formed.
The additional formulation or polymerizable composition may contain one or more additives, thereby extracting much more in the polymerized lens product before extraction compared to the lens product obtained from the bulk formulation. Possible components may be present. For example, if the pre-extracted polymerized silicone hydrogel contact lens product obtained from the bulk formulation has an extractable component content of 15%, the same with the addition of 15% (w / w) amount of diluent The second pre-extracted polymerized silicone hydrogel contact lens product obtained from the formulation can be interpreted as having an extractable component content of 30% (w / w). After the extraction and hydration procedure, the dry weight of the silicone hydrogel contact lens obtained from the lens product before extraction will be 70% of the dry weight of the lens product before extraction.
Another aspect of the invention relates to a polymerized silicone hydrogel contact lens product prior to extraction. The lens product can be interpreted as, for example, a product produced from a curing or polymerization procedure in a mold cavity and not subjected to an extraction procedure or in contact with an extraction composition. In certain embodiments, the contact lens product has a dry weight that is at least 10% greater than the dry weight of the body member after subjecting the body member to an extraction step to form an extracted polymerized silicone hydrogel contact lens product. It includes a body member before being extracted. For example, the body member prior to extraction may comprise an extractable content of at least 10% (w / w) of the body member prior to extraction. In a further embodiment, the extractable component content is greater than 15% (w / w) of the body member prior to extraction and less than 80% (w / w) of the body member prior to extraction. In some embodiments, the extractable component content is greater than 20% (w / w) of the body member prior to extraction and less than 75% (w / w) of the body member prior to extraction. The pre-extracted body member of the pre-extracted polymerized silicone hydrogel contact lens product of the present invention can include one or more removable additives, such as additives that can be removed during the extraction procedure. For example, the body member can include one or more compatibilizers, mold release aids, de-lens aids, wettability enhancers, and ionoflux reducers. These removable additives can be interpreted as non-reactive additives or can be interpreted as reactive additives that can be removed from the polymerized silicone hydrogel contact lens product during the extraction procedure.

  Another aspect of the invention relates to a polymerizable silicone hydrogel contact lens precursor composition. The polymerizable silicone hydrogel contact lens precursor composition of the present invention comprises a lens forming component, such as a monomeric material, and one or more optional additives as described herein, with a substantial amount of a removable component. A polymerized silicone hydrogel contact lens product is formed. In certain embodiments, the polymerizable silicone hydrogel contact lens precursor composition comprises a polymerizable silicon-containing component and a polymerizable non-silicon-containing component. The two components are formulated as a polymerizable silicone hydrogel contact lens precursor composition. A portion of this precursor composition is removed from the polymerized silicone hydrogel contact lens product made from the precursor composition. This portion is present in an amount of at least 10% (w / w) of the polymerized silicone hydrogel contact lens product prior to extraction. In some embodiments, the precursor composition includes a first monomer having a first reactivity ratio and a second monomer having a second reactivity ratio that is lower than the first reactivity ratio. As will be appreciated by those skilled in the art, the reactivity ratio can be defined as the ratio of the reaction rate constant of adding each propagating species's own monomer to the rate constant of the addition of other monomers. The composition may include a cross-linking agent having a reactivity ratio similar to the first reactivity ratio. In certain embodiments, the lens precursor composition may include one or more removable additives. For example, embodiments of the lens precursor composition may include one or more compatibilizers that can be removed, mold release aids, de-lens aids, wettability enhancers, and ionoflux reducers.

Yet another aspect of the present invention relates to a method for producing an eye compatible silicone hydrogel contact lens. In certain embodiments, the method forms a lens body comprising a silicone hydrogel material and having an eye-acceptable surface wettability and a dry weight not exceeding 90% of the dry weight of the lens body prior to extraction. The process of carrying out is included. The method includes the step of extracting an extractable component from the polymerized silicone hydrogel contact lens product prior to extraction (wherein the extractable component content is at least the polymerized silicone hydrogel contact lens product prior to extraction). 10% (w / w)). The method may also include the step of forming a pre-extracted silicone hydrogel contact lens product of the present invention and a polymerizable silicone hydrogel contact lens precursor composition useful in the manufacture of the silicone hydrogel contact lens of the present invention.
Further embodiments of the lens, lens product, composition and method will be apparent from the following description, drawings, examples and claims. As will be apparent from the foregoing description and the following description, each feature and every feature disclosed in this specification, and every combination and every combination of features, is characterized by the fact that the features included in the combination are consistent with each other. It is included in the scope of the present invention as a condition. In addition, any feature or combination may be specifically excluded from any embodiment of the present invention. Additional aspects and advantages of the present invention are set forth in the following description and claims, particularly when considered in conjunction with the accompanying examples and drawings.

[Detailed explanation]
FIG. 1 shows a method for producing a silicone hydrogel contact lens. The illustrated method is a cast molding method for silicone hydrogel contact lenses. Cast molded contact lenses do not need to be adapted to be further machined and modified for use on the eye. A silicone hydrogel contact lens of the present invention produced using a cast molding procedure such as that shown in FIG. 1 can be interpreted as a cast molded silicone hydrogel contact lens. Furthermore, if no further machining is used to change the lens design, the lens can be interpreted as a fully molded silicone hydrogel contact lens.

As used herein, the term “hydrogel” refers to a network or matrix of polymer chains, some or all of which are water soluble and may contain a high percentage of water. Hydrogel refers to polymeric materials, including contact lenses, that are water swellable or water swelled. Thus, the hydrogel may be unhydrated and water swellable, or partially hydrated and swollen with water, or fully hydrated and swollen with water. The term “silicone hydrogel” or “silicone hydrogel material” refers to a hydrogel comprising a silicon component or a silicone component. For example, a silicone hydrogel includes one or more hydrophilic silicon-containing polymers. Silicone hydrogel contact lenses are contact lenses, including vision correction contact lenses, that include a silicone hydrogel material.
A silicone-containing component is a component that contains at least one [—Si—O—Si] group in a monomer, macromer or prepolymer. The silicone-containing component may have O attached to Si in an amount greater than 20% by weight of the total molecular weight of the silicone-containing component, such as greater than 30% by weight. Useful silicone-containing components include polymerizable functional groups such as acrylate, methacrylate, acrylamide, methacrylamide, N-vinyl lactam, N-vinylamide, and styryl functional groups. Some silicone-containing components useful in this lens are found in US Pat. Nos. 3,808,178; 4,120,570; 4,136,250; 4,153,641; 4,740,533; 5,034,461 and 5,070,215, and EP080539.
Further examples of suitable silicone-containing monomers are polysiloxanylalkyl (meth) acrylic monomers, including but not limited to methacryloxypropyltris (trimethylsiloxy) silane, pentamethyldisiloxanylmethyl methacrylate, and And methyldi (trimethylsiloxy) methacryloxymethylsilane.
One useful class of silicone-containing components is poly (organosiloxane) prepolymers such as α, ω-bismethacryloxy-propyl polydimethylsiloxane. Another example is mPDMS (monomethacryloxypropyl-terminated mono-n-butyl terminated polydimethylsiloxane). Another useful class of silicone-containing ingredients includes, but is not limited to, silicone-containing vinyl carbonate or vinyl carbamate monomers, but is not limited to 1,3-bis [4- (vinyloxycarbonyloxy) but-1-yl]. Tetramethylsiloxane 3- (vinyloxycarbonylthio) propyl- [tris (trimethylsiloxysilane); 3- [tris (trimethylsiloxy) silyl] propylallylcarbamate; 3- [tris (trimethylsiloxy) silyl] propylvinylcarbamate; trimethylsilyl Examples of suitable materials include substances represented by the following formula: ethyl vinyl carbonate, and trimethylsilylmethyl vinyl carbonate.

  Another example of a suitable material is a substance represented by the following formula.

In addition to the silicon-containing component, the lens, lens product, and composition may include one or more hydrophilic components. Hydrophilic components include those components that when combined with the remaining reactive components can give the resulting lens a moisture content of at least about 20%, such as at least about 25%. Suitable hydrophilic components may be present in an amount of about 10 to about 60% by weight based on the weight of all reactive components. About 15 to about 50% by weight, for example, about 20 to about 40% by weight. The hydrophilic monomer that can be used to produce the polymer for the lens has at least one polymerizable double bond and at least one hydrophilic functional group. Examples of polymerizable double bonds are acrylic, methacrylic, acrylamide, methacrylamide, fumarate, malein, styryl, isopropenylphenyl, O-vinyl carbonate, O-vinyl carbamate, allyl, O-vinyl acetyl and N-vinyl lactam And N-vinylamide double bond. Such hydrophilic monomers are themselves used as crosslinking agents. “Acrylic type” or “acrylic-containing” monomers include N, N-dimethylacrylamide (DMA), 2-hydroxyethyl acrylate, glycerol methacrylate, 2-hydroxyethyl methacrylamide, polyethylene glycol monomethacrylate, methacrylic acid, acrylic acid and its Acrylic groups (CR′H═CRCOX) that are also known to polymerize readily, such as mixtures, wherein R is H or CH ₃ , R ′ is H, alkyl or carbonyl, and X is O Or N).
Hydrophilic vinyl-containing monomers that can be incorporated into the lens material include N-vinyl lactam (e.g., N-vinylpyrrolidone (NVP)), N-vinyl-N-methylacetamide, N-vinyl-N-ethylacetamide, N And monomers such as -vinyl-N-ethylformamide, N-vinylformamide, N-2-hydroxyethyl vinylcarbamate, and N-carboxy-β-alanine N-vinyl ester. In one embodiment, the hydrophilic vinyl-containing monomer is NVP.
Other hydrophilic monomers that can be utilized in the present lenses include polyoxyethylene polyols having one or more terminal hydroxyl groups replaced with functional groups containing polymerizable double bonds. Examples include polyethylene glycol having one or more terminal hydroxyl groups replaced with a functional group containing a polymerizable double bond. Examples include reacting with one or more molar equivalents of end-capping groups such as isocyanatoethyl methacrylate (“IEM”), methacrylic anhydride, methacryloyl chloride, vinyl benzoyl chloride, etc. Or polyethylene glycol which has one or more polymerizable terminal olefinic groups bonded via a linking component such as an ester group.
Further examples are the hydrophilic vinyl carbonate or vinyl carbamate monomers disclosed in US Pat. No. 5,070,215, and the hydrophilic oxazolone monomers disclosed in US Pat. No. 4,190,277. Other suitable hydrophilic monomers will be apparent to those skilled in the art. More preferred hydrophilic monomers that can be incorporated into the polymer of the present invention include N, N-dimethylacrylamide (DMA), 2-hydroxyethyl acrylate, glycerol methacrylate, 2-hydroxyethyl methacrylamide, N-vinylpyrrolidone (NVP), polyethylene glycol Examples thereof include hydrophilic monomers such as monomethacrylate and polyethylene glycol dimethacrylate. In some embodiments, hydrophilic monomers such as DMA, NVP and mixtures thereof are used.
Additional examples of materials used to make silicone hydrogel contact lenses include those disclosed in US Pat. No. 6,867,245.

The illustrated method includes the step 102 of placing a lens precursor composition on or in a contact lens mold member. In the context of this application, the lens precursor composition can be interpreted as a polymerizable silicone hydrogel lens precursor composition 202, as shown in FIG. A polymerizable silicone hydrogel lens precursor composition can be interpreted as a pre-polymerization or pre-curing composition suitable for polymerization. In the present specification, the polymerizable composition of the present invention may be referred to as a monomer mix or a reaction mixture. Preferably, the polymerizable composition or lens precursor composition does not polymerize prior to curing or polymerization of the composition. However, the polymerizable composition or lens precursor composition may be partially polymerized prior to undergoing the curing process. The lens precursor composition is supplied to a container, dispensing device, or contact lens mold prior to the curing or polymerization procedure, as described herein. Returning to FIG. 1, the lens precursor composition is placed on the lens forming surface of the female contact lens mold member. The female contact lens mold member can be interpreted as the first contact lens mold member or the front contact lens mold member. For example, a female contact lens mold member has a lens forming surface that defines a front or front surface of a contact lens manufactured from the contact lens mold.
The first contact lens mold member is placed in contact with the second contact lens mold member to form a contact lens mold having a contact lens shaped cavity. Accordingly, the method shown in FIG. 1 includes the step 104 of closing the contact lens mold by placing two contact lens mold members in contact to form a contact lens shaped cavity. A polymerizable silicone hydrogel lens precursor composition 202 is in the contact lens shaped cavity. The second contact lens mold member can be interpreted as a male contact lens mold member or a rear contact lens mold member. For example, the second contact lens mold member includes a lens forming surface that defines a rear surface of a contact lens manufactured in the contact lens mold.
In step 106, the method cures the polymerizable silicone hydrogel lens precursor composition to form a polymerized silicone hydrogel contact lens product 204 prior to extraction, as shown in FIG. During curing, the lens forming component of the polymerizable silicone hydrogel lens precursor composition polymerizes to form a polymerized lens product. Therefore, the curing process can be interpreted as a polymerization process. Curing step 106 may include subjecting the polymerizable lens precursor composition to radiation effective to polymerize the components of the lens precursor composition. For example, the curing step 106 may include subjecting the polymerizable lens precursor composition to a polymerization amount of heat, ultraviolet (UV) radiation, or the like. The curing step may include a step of curing the composition in an oxygen free environment. For example, the curing process can occur in the presence of nitrogen or other inert gas.

The polymerized silicone hydrogel contact lens product 204 before being extracted refers to the polymerized product prior to undergoing an extraction procedure that removes substantially all extractable components from the polymerized product. Prior to contact with the extraction composition, the polymerized silicone hydrogel contact lens product prior to extraction can be provided on or in a contact lens mold, extraction tray, or other device. For example, in the lens cavity of the contact lens mold after the curing procedure, or on or in one contact lens mold member after the release of the contact lens mold, or the extraction tray or other after the de-lensing procedure and before the extraction procedure The polymerized silicone hydrogel contact lens product prior to extraction can be provided on or in the device. The polymerized silicone hydrogel contact lens product prior to extraction includes a lens-forming component, such as a lens-shaped silicon-containing polymer network or matrix, and a removable component that can be removed from the lens-forming component. Removable components can be construed to include unreacted monomers, oligomers, partially reacted monomers, or other materials that are no longer covalently bonded or otherwise immobilized with respect to the lens-forming component. . The removable component includes one or more additives such as diluents and other organic additives that can be extracted from the polymerized lens product during the extraction procedure, as discussed herein. Can also be interpreted. Thus, the removable component material is not cross-linked to the polymer backbone, network, or matrix of the lens body, or is otherwise linear, non-cross-linked, of the extractable material that is not fixed in relation thereto. Or branched polymers may also be included.
After curing the polymerizable lens precursor composition, the method includes a mold release step 108 of the contact lens mold. The mold release process refers to the process of separating two mold parts of the mold containing the polymerized contact lens product or polymerized device before being extracted, for example a male mold and a female mold. The polymerized silicone hydrogel contact lens product prior to extraction is on one of the released mold members. For example, the polymerized silicone hydrogel contact lens product can be on a male mold member or a female mold member.
Next, as shown in FIG. 1, during the delensing step 110, the polymerized silicone hydrogel contact lens product 204 prior to extraction on the contact lens mold member is separated from the contact lens mold member. The Depending on which mold member the polymerized contact lens product remains attached during the release of the contact lens mold, it is polymerized before being extracted from the male mold member or the female mold member. The contact lens product is delensed.
After delensing the silicone hydrogel contact lens product before extraction, the method includes a step 112 of extracting extractable material from the silicone hydrogel contact lens product before extraction. The extraction step 112 results in an extracted silicone hydrogel contact lens product 206, as shown in FIG. The extraction step 112 refers to a procedure in which the polymerized silicone hydrogel contact lens product prior to extraction is contacted with one or more extraction compositions. For example, a polymerized silicone hydrogel contact lens product or a batch of polymerized silicone hydrogel contact lens products can be contacted with one or more volumes of liquid extraction medium. The extraction medium can include one or more solvents. For example, the extraction medium includes ethanol, methanol, propanol, and other alcohols. As extraction medium, a mixture of alcohol and water, for example a mixture of 50% ethanol and 50% deionized water, or a mixture of 70% ethanol and 30% deionized water, or 90% ethanol and 10% deionized water. Also included is a mixture of ionic water. Alternatively, the extraction medium may be substantially or completely alcohol free and may include one or more agents that facilitate removal of hydrophobic unreacted components from the polymerized silicone hydrogel lens product. For example, the extraction medium may comprise, consist essentially of, or consist entirely of water, buffer, and the like. The extraction step 112 can be performed at various temperatures. For example, extraction can occur at room temperature (eg, about 20 ° C.), or extraction can occur at elevated temperatures (eg, about 25 ° C. to about 100 ° C.). Further, in certain embodiments, the extraction step 112 may include contacting the lens product with a mixture of alcohol and water, which may be the last step in a multi-step extraction procedure.
After extracting the polymerized silicone hydrogel contact lens product prior to extraction, the method includes a step 114 of hydrating the extracted polymerized silicone hydrogel contact lens product. The hydration step 114 comprises contacting the extracted polymerized silicone hydrogel contact lens product or one or more batches of the product with water or an aqueous solution, as shown in FIG. 2, to hydrate the silicone hydrogel contact lens. Forming 208 may be included. For example, the extracted polymerized silicone hydrogel contact lens product can be hydrated by placing it in two or more separate volumes of water, or deionized water. In certain embodiments, the hydration step 114 may be combined with the extraction step 112 so that both steps are performed at a single station on the contact lens production line. The hydration step 114 is performed in a container at room temperature or at a high temperature, and may be performed at high pressure if desired. For example, hydration can occur in water at a temperature of about 120 ° C. (eg, 121 ° C.) and a pressure of 103 kPa (15 psi).
As is apparent from the above, the pre-extracted polymerized silicone hydrogel contact lens product and the extracted polymerized silicone hydrogel contact lens product can be interpreted as water swellable products or elements and are hydrated. Silicone hydrogel contact lenses can be interpreted as products or elements swollen with water. As used herein, a silicone hydrogel contact lens refers to a silicone hydrogel element that has undergone a hydration process. Thus, a silicone hydrogel contact lens can be interpreted as a fully hydrated silicone hydrogel contact lens, a partially hydrated silicone hydrogel contact lens, or a dehydrated silicone hydrogel contact lens. A dehydrated silicone hydrogel contact lens refers to a contact lens that has undergone a hydration procedure and subsequently dehydrated to remove water from the lens.
After hydrating the extracted silicone hydrogel contact lens product to produce the silicone hydrogel contact lens, the method includes packaging 116 the silicone hydrogel contact lens 208. For example, the silicone hydrogel contact lens 208 can be placed in a blister pack or other suitable container containing a volume of liquid, such as saline, such as buffered saline. Examples of liquids suitable for the lens include phosphate buffered saline and borate buffered saline. As shown in step 118, the blister pack or container can be sealed and subsequently sterilized. For example, the packaged silicone hydrogel contact lens can be exposed to sterilizing amounts of radiation or heat, such as by autoclaving, gamma radiation, e-beam radiation, or ultraviolet light.

The eye-compatible silicone hydrogel contact lens of the present invention is obtained by supplying a relatively large amount of removable material to the polymerized silicone hydrogel contact lens product prior to extraction. Polymerization prior to extraction with one or more removable materials, such as extractable materials, that is at least 10% (W / W) of the removable component, ie, the weight of the polymerized silicone hydrogel contact lens product prior to extraction. The resulting silicone hydrogel lens product can be extracted and hydrated to form a silicone hydrogel contact lens having an eye-acceptable surface wettability. The lens allows the lens to be worn comfortably in the human eye for long periods of time, such as at least 1 day, at least 1 week, at least 2 weeks, or about 1 month without having to remove the lens from the eye Oxygen permeability, surface wettability, modulus, moisture content, ionoflux, design, and combinations thereof.
As used herein, “eye-compatible silicone hydrogel contact lens” refers to a silicone hydrogel contact lens that can be worn by the human eye without substantial human experience or report such as eye irritation. Can be interpreted. Eye-compatible silicone hydrogel contact lenses have eye-acceptable surface wettability, typically significant corneal swelling, corneal dehydration ("dry eye"), epithelial arcuate lesions (superior-epithelial arcuate lesion) ("SEAL") or other significant discomfort is not caused or is not accompanied by such discomfort. Silicone hydrogel contact lenses with ophthalmically acceptable surface wettability are such that the lens wearer will experience or report discomfort associated with placing or wearing the silicone hydrogel contact lens in the eye, It can be construed to mean a silicone hydrogel contact lens that does not adversely affect the tear film of the lens wearer's eye. Eye-compatible silicone hydrogel contact lenses meet the clinical acceptance requirements of daily or long-wearing contact lenses.
The silicone hydrogel contact lens includes a lens body having an eye-acceptable wettable surface, such as an anterior surface and a posterior surface. Wettability represents the hydrophilicity of one or more surfaces of a contact lens. As used herein, if a lens receives a score of 3 or more in a wettability assay performed as follows, the surface of the lens is considered wettable or is considered to have acceptable wettability to the eye. Immerse the contact lens in distilled water and remove it from the water to determine the length of time it takes for the water film to retract from the lens surface (e.g. water break up time (water BUT or WBUT )). This assay gives a lens grade with a linear score of 1-10, with a score of 10 pointing to the lens where the drop retracts from the lens over 20 seconds. A silicone hydrogel contact lens having a BUT of water of more than 5 seconds, such as at least 10 seconds, more desirably at least 15 seconds, can be a silicone hydrogel contact lens having an eye-acceptable surface wettability. Wettability can also be determined by measuring the contact angle on one or both sides of the lens. The contact angle may be a dynamic contact and a static contact angle. A smaller contact angle generally means that the wettability of the contact lens surface is high. For example, the wettable surface of a silicone hydrogel contact lens can have a contact angle of less than about 120 degrees. However, in certain embodiments of the lens, the lens has a contact angle not exceeding 90 degrees, and in further embodiments, the silicone hydrogel contact lens has an advancing contact angle of less than about 80 degrees.

Polymerized compositions of the present invention, such as polymerized silicone hydrogel contact lens products prior to extraction, in polymerizable compositions of the present invention, such as the polymerizable silicone hydrogel contact lens precursor compositions of the present invention. It has been discovered that by adjusting the amount or type of reactive component or combination of reactive and non-reactive components therein, a silicone hydrogel contact lens having surface wettability acceptable to the eye can be obtained. The silicone hydrogel contact lens with surface wettability acceptable to the eye of the present invention does not require a surface treatment or polymer wetting agent IPN to provide surface wettability, and a polar resin contact to provide surface wettability There is no need for manufacturing in a lens mold. For example, without a surface treatment or polymer wetting agent IPN, a silicone hydrogel contact lens having a surface wettability acceptable to the eye of the present invention can be obtained from a nonpolar resin contact lens mold or a hydrophobic resin contact lens mold. it can.
In this specification, “a non-polar resin contact lens mold” or “a hydrophobic resin contact lens mold” refers to a contact lens mold formed or manufactured from a non-polar resin or a hydrophobic resin. Thus, nonpolar resin-based contact lens molds can include nonpolar or hydrophobic resins. For example, such contact lens molds may include one or more polyolefins or may be formed from a polyolefin resin material. Examples of nonpolar resin contact lens molds used in the context of this application include polyethylene contact lens molds, polypropylene contact lens molds, and polystyrene contact lens molds. Nonpolar resin-based contact lens molds typically have a hydrophobic surface. For example, a nonpolar resin mold or a hydrophobic resin mold may have a static contact angle of about 90 degrees or greater as determined by a captive bubble method. With such a contact angle, normal silicone hydrogel contact lenses made from the mold have surface wettability that is clinically unacceptable.

Polymerization prior to extraction by supplying relatively slowly reacting monomers to the polymerizable composition, for example by supplying two or more monomer types of different reactivity to the same polymerizable composition The amount of removable component in the resulting silicone hydrogel contact lens product can be adjusted. Slowly reacting monomers, such as monomers that do not fully crosslink into the network during the curing procedure, in the polymerizable composition are relatively large amounts of removable components in the polymerized silicone hydrogel contact lens product. Can give. Non-fully crosslinked materials such as unreacted or partially reacted monomers, oligomers, linear polymers, slightly crosslinked components, etc. are extracted from the polymerized components of the polymerized silicone hydrogel contact lens product.
There are removable additives in certain polymerizable compositions and polymerized silicone hydrogel contact lens products of the present invention. For example, some of the polymerizable compositions and polymerized silicone hydrogel contact lens products of the present invention contain one or more additives that can be removed from the polymerized silicone hydrogel contact lens product during the extraction procedure.
The term “additive” in the context of the present application means a compound or chemical agent that is supplied to the polymerizable silicone hydrogel contact lens precursor composition or the polymerized silicone hydrogel contact lens product prior to extraction. Not necessary for the production of silicone hydrogel contact lenses. However, the inclusion of removable additives facilitates the processing of contact lenses during the manufacture of contact lenses compared to silicone hydrogel contact lenses obtained from the same precursor composition without the additives or combinations thereof, One or more properties of the silicone hydrogel contact lens may be improved. As used herein, the additive can be removed from the polymerized silicone hydrogel contact lens product prior to extraction. For example, the additive is substantially non-reactive or non-reactive with the other components of the polymerizable silicone hydrogel lens precursor composition. For example, the additive is not substantially a covalently integral part of the resulting polymerized lens product. Depending on their molecular weight and shape, most if not all additives can be extracted from the polymerized silicone hydrogel contact lens product. Thus, additives in the composition can be extracted from the polymerized silicone hydrogel contact lens product during the extraction procedure.
In certain embodiments, the additive may be referred to as a diluent, an agent that does not substantially react, or an extractable. The diluent may be an alcohol or non-alcohol material. Diluents may be present in an amount from about 1% to about 60% (w / w) of the lens precursor composition. Other undiluted base additives may be present in amounts less than about 10% (w / w) if desired. Additives supplied in the present composition assist in the formation of a polymerizable silicone hydrogel contact lens precursor composition, for example by facilitating the formation of a homogeneous composition or a composition that does not phase separate; Polymerized silicone hydrogel contact lens product prior to extraction by promoting release of the contact lens mold and / or by promoting delensing of the contact lens product from the contact lens mold Improve the adjustment of the physical parameters of the contact lens, for example by reducing the variability of the physical parameters of the contact lens in a population of contact lenses, for example in different batches of contact lenses To improve the wettability of contact lens surfaces, for example Improving the wettability of the contact lens; positively affecting the modulus of the contact lens by, for example, reducing the modulus or increasing the modulus as desired; and, for example, a lens product without additives By reducing the ion flux of the contact lens as compared to the contact lens obtained from the above, it is possible to positively influence the ion flux of the contact lens. Therefore, the additives supplied in the composition include compatibilizers, mold release aids, de-lens aids, physical parameter modifiers, wettability enhancers, influencing agents, ionophores. It can be interpreted as a flux reducing agent or a combination of any one or more of these. The improvement or improvement obtained with the additive is the same polymerizable silicone hydrogel contact lens precursor composition lacking the additive or the polymerized silicone hydrogel contact lens product before extraction, or such polymerization. This is evident when compared to silicone hydrogel contact lenses obtained from possible compositions or polymerized products.
The compatibilizer disclosed herein can improve or enhance the miscibility of the components of the precursor composition of the present invention. For example, compatibilizers can reduce the phase separation associated with silicon-containing polymers and other lens-forming components as compared to formulations without compatibilizers.
Supplying removable additives to certain inventive polymerizable compositions and polymerized products includes exposing the contact lens or lens product to a surface treatment or including an IPN of a polymer wetting agent such as PVP Without facilitating the production of silicone hydrogel contact lenses having, for example, eye-compatible surface wettability. For example, the additive is homogeneously distributed throughout the polymerization composition and is substantially, if not completely, removed from the polymerized overall product during the extraction procedure. Furthermore, the additives disclosed herein are not polymer wetting agents that are mixed with the composition prior to polymerization and subsequently mixed into the polymerized object to form an IPN. The contact lenses are produced with little physical or dimensional variability between batches, and as a result, the yield of clinically acceptable, eye-compatible silicone hydrogel contact lenses can be improved. . Additives can be in liquid or solid form and can include hydrophobic or amphiphilic compounds or agents.
Additives, including diluents, useful in the present compositions and lens products include hydrophilic groups linked to hydrophobic groups, such as hydroxyl groups with alkane chains, siloxane molecular backbone linked to hydrophilic PEG sections. And so on. Examples of additives include, but are not limited to, polydimethylsiloxane-co-PEG polymer having a molecular weight of about 10,000 daltons or less, ethylene glycol stearate, diethylene glycol monolaurate, C ₂ -C ₂₄ alcohol and / or C ₂ -C ₂₄ amine. Additives include one or more polar or hydrophilic end groups such as, but not limited to, hydroxyl, amino, sulfhydryl, phosphate and carboxyl groups, and other additives present in the composition of the additive. It is also possible to promote miscibility with the material. The additive may be present in an amount from about 2% (w / w) to about 60% (w / w) in the polymerizable silicone hydrogel precursor composition. For example, the composition includes one or more additives present in an amount of about 5% to about 50% (w / w). Further examples of polymerizable compositions include one or more additions present in an amount of about 20% or about 25% or about 30% or about 35% or about 40% or about 45% or about 50% or about 55% Contains agents.

The silicone hydrogel contact lens includes a lens body having an eye-acceptable surface wettability. For example, the lens body of the present silicone hydrogel contact lens has a front surface and a rear surface, and each surface has surface wettability acceptable to the eye.
In one embodiment, the lens body of the silicone hydrogel contact lens comprises a silicone hydrogel material. The lens body has a dry weight not exceeding 90% of the dry weight of the lens body before extraction. For example, the lens body of the polymerized silicone hydrogel contact lens product prior to extraction has a dry weight of X. After the extraction procedure, the lens body of the extracted polymerized silicone hydrogel contact lens product has a dry weight of 0.9X or less. As described above, the polymerized silicone hydrogel contact lens product prior to extraction can be contacted with several volumes of a plurality of organic solvents and hydrated to produce a silicone hydrogel contact lens. Next, the hydrated silicone hydrogel contact lens is dehydrated and weighed to determine the dry weight of the lens body of the silicone hydrogel contact lens. For example, in one method, the polymerized silicone hydrogel contact lens product prior to extraction is de-lensed from the contact lens mold and weighed to dry weight the polymerized silicone hydrogel contact lens product prior to extraction. give. The unextracted lens product is then contacted with alcohol for about 6 hours and then hydrated with water. The hydrated lens is then dried for about 1 hour at about 80 ° C. and then for about 2 hours at about 80 ° C. under vacuum. The dried lens is weighed to determine the dry weight of the lens body of the silicone hydrogel contact lens. The dry weight is compared to determine the amount of extractable material present in the polymerized silicone hydrogel contact lens product prior to extraction. A pre-extracted polymerized lens product having an extractable component content of about 40% comprises a silicone hydrogel contact lens lens body having a dry weight that is about 60% of the pre-extracted lens product. Generate. A pre-extracted polymerized lens product having an extractable component content of about 70% comprises a lens body of a silicone hydrogel contact lens having a dry weight that is about 30% of the pre-extracted lens product. Generate.
The following equation can be used to determine the amount of extractables present in the polymerized silicone hydrogel contact lens product prior to extraction, ie the extractable component content.
E = ((dry weight of lens product before extraction−dry weight of extracted and hydrated contact lens) / dry weight of lens product before extraction) × 100.
E is the percentage of extractables present in the lens product before being extracted.
For example, the polymerized silicone hydrogel contact lens product prior to extraction can have a dry weight of about 20 mg. When the silicone hydrogel contact lens obtained from the product has a dry weight of about 17 mg, the silicone hydrogel contact lens has a dry weight that is 85% of the dry weight of the lens product before being extracted. including.
The pre-extracted lens product can be interpreted as having an extractable component content of about 15% (w / w). As another example, the polymerized silicone hydrogel contact lens product before extraction has a dry weight of about 18 mg, and the dehydrated silicone hydrogel contact lens obtained from the lens product has a dry weight of about 13 mg. If so, the silicone hydrogel contact lens comprises a lens body having a dry weight that is about 72% of the lens product prior to extraction. The pre-extracted polymerized silicone hydrogel contact lens product has an extractable component content of about 28% (w / w).
In certain embodiments, the dry weight of a silicone hydrogel contact lens (ie, a silicone hydrogel contact lens that has undergone extraction and hydration procedures) is greater than 25% of the dry weight of the lens body prior to extraction. For example, the dry weight of the lens body after extraction can be about 25% to about 90% of the dry weight of the lens body before extraction. The lens of some embodiments includes a lens body having a dry weight of about 50% to about 85% of the dry weight of the lens body before being extracted.
As discussed herein, lens precursor compositions without removable additives or silicone hydrogel contact lens products prior to extraction (eg, lens products obtained from “bulk formulations”) The silicone hydrogel contact lens obtained from) has an extractable component content in the pre-extracted lens product of greater than 10%, such as at least 15%, at least 20%, at least 25% or more. In some cases, it may have surface wettability acceptable to the eye. Inclusion of one or more removable additives in the precursor composition or the polymerized pre-extracted lens product increases the extractable component content compared to the bulk product lens product and is consequently acceptable to the eye. The resulting silicone hydrogel contact lens has surface wettability.
Accordingly, the present silicone hydrogel contact lens comprising a lens body having a dry weight greater than 90% of the dry weight of the lens body prior to extraction is a contact lens obtained from a bulk formulation and a formulation or lens comprising one or more removable substances It can be interpreted as a contact lens obtained from the product.

In contrast, previous descriptions of silicone hydrogel contact lenses obtained from diluent-containing formulations do not include formulations without diluent, which have a high extractable component content. Such lenses often require a surface treatment or polymeric IPN to give the silicone hydrogel contact lens an acceptable surface wettability to the eye.
Although the pre-extracted polymerized silicone hydrogel contact lens product of the present invention has a relatively large amount of extractable material, the extracted form of the present silicone hydrogel contact lens has little extractable material in the lens body. Absent. In certain embodiments, the amount of extractable material remaining in the extracted lens is from about 0.1% to about 4%, such as from about 0.4% to about 2% (w / w). These additional extractable materials can be determined by contacting the extracted contact lens with an additional amount of a powerful solvent, such as chloroform.
If the lens body of the silicone hydrogel contact lens has a dry weight that does not exceed 90% of the dry weight of the lens body before extraction, the hydrated lens body of the silicone hydrogel contact lens is compatible with the eye, and Has surface wettability acceptable to the eye. In contrast, a silicone hydrogel contact lens prior to extraction (with a removable component content that is less than 10% (w / w) of the lens product, such as about 5 to about 8% (w / w)) Is obtained from a non-polar resin contact lens mold, the hydrated silicone hydrogel contact lens thus produced does not have eye-acceptable surface wettability. Thus, such a non-wetting lens can be interpreted as a lens comprising a lens body having a dry weight of more than 90%, for example 92%, of the lens body before extraction.
In addition, the extractable component is present in the polymerizable silicone hydrogel lens precursor composition and the polymerized silicone hydrogel contact lens product prior to extraction and distributed throughout them, so that the surface treated silicone The lens product and contact lens can be distinguished from hydrogel contact lenses. Distinguishing the lens product and the contact lens from the silicone hydrogel contact lens with the polymer wetting agent IPN because the extractable component is extractable from the lens product and is substantially absent from the hydrated contact lens. Can do.
The silicone hydrogel contact lens may comprise a lens body obtained from a non-polar resin contact lens mold. This lens body has substantially the same surface morphology when examined in a hydrated and dehydrated state. Furthermore, such a hydrated lens body may have a surface roughness that is slightly lower than the surface roughness of the dehydrated lens body. For example, the lens body of the present lens may have a surface that includes a nanometer-sized peak that is evident when analyzing the root mean square (RMS) roughness data of the lens surface. The lens body may include regions between peaks that provide reduced roughness but swell differentially as compared to peaks to provide a substantially similar surface morphology. For example, when the lens body hydrates, the peak height may decrease, but the peak shape remains substantially the same.
Additionally or alternatively, embodiments of silicone hydrogel contact lenses molded from the non-polar resin molds of the present invention can be used in electronic scanning electron microscopes, transmission electron microscopes, or scanning transmission electron microscopes. When examined under a microscope, it may include a lens body having a silicon rich domain and a silicon poor domain that can be visually identified. A silicon poor domain is interpreted as a region in the lens that is substantially or completely free of silicon based on chemical analysis. The silicon poor domain may be larger than that in a surface treated silicone hydrogel contact lens or a silicone hydrogel contact lens comprising a polymer wetting agent IPN. The size of the silicon rich domain, the silicon poor domain, or both domains can be determined using conventional image analysis software and devices, such as an image analysis system available from Bioquant (Tennessee). An image analysis software system can be used to define the boundary between the silicon rich domain and the silicon poor domain and determine the cross-sectional area, diameter, volume, etc. of the domain. In certain embodiments, the silicon poor domain has a cross-sectional area that is at least 50%, at least 60%, at least 70%, at least 80%, or at least 90% greater than the silicon pore domain of other silicone hydrogel contact lenses.

In another embodiment, the silicone hydrogel contact lens is obtained from a polymerized silicone hydrogel contact lens product (having a removable component content of at least 10% (w / w) of the lens product) prior to extraction. Including the lens body. The range body of the polymerized silicone hydrogel contact lens prior to extraction is free or free of removable or non-reactive additives such as diluents, compatibilizers and the like. Such lens bodies are obtained from bulk formulations as described herein. These lens bodies have a removable component content of at least 10% (w / w), and in certain embodiments, the lens bodies are at least 15% (w / w), at least 20% (w / w), at least 25 % (w / w), about 30% (w / w), or more of the removable component content. For example, in certain embodiments, the polymerized contact lens product prior to extraction has 10% (w / w) to about 30% (w / w) extractable components and is non-reactive additive There is no. In a further embodiment, the polymerized contact lens product prior to extraction has an extractable component content of 15% (w / w) to about 30% (w / w) and is free of non-reactive additives. . In further embodiments, the lens body may include one or more non-reactive additives and a removable component content that is greater than the amount present in a similar lens body without non-reactive additives. In certain embodiments, the removable component content does not exceed 75% (w / w) of the lens product. Thus, embodiments of the present silicone hydrogel contact lenses are from pre-extracted polymerized silicone hydrogel contact lens products having a removable component content greater than 10% (w / w) and less than 75% (w / w). Includes the resulting lens body. For example, some pre-extracted polymerized silicone hydrogel contact lens products have a removable component content of about 15% (w / w) to about 65% (w / w). The removable components include extractable materials or extractables that are extracted during the extraction procedure. Further, the removable component may include other materials, such as volatile materials, that can be passively or actively removed from the polymerized silicone hydrogel contact lens product prior to extraction prior to extraction. For example, some of the removable components can evaporate between the mold release process and the extraction process.
In certain embodiments, the removable component of the polymerized silicone hydrogel contact lens product prior to extraction comprises at least one removable additive. As discussed herein, the removable additive may be a non-reactive additive or a reactive additive that results in a product that can be removed from the polymerized silicone hydrogel contact lens product prior to extraction. It's okay. Examples of removable additives that may be included in the pre-extracted polymerized silicone hydrogel contact lens product of the present invention include compatibilizers, mold release aids, de-lens aids, wettability enhancers, ionoflux reduction Agents, modulus affecting agents, chain transfer agents, and combinations thereof.
In certain embodiments, the removable component comprises a hydrophobic additive, an amphiphilic additive, or a combination thereof. For example, the removable component can include one or more additives selected from the group consisting of reactive alcohols, non-reactive hydrophilic silicone polymers, and combinations thereof. As a further example, the additive may be selected from the group consisting of ethylene glycol stearate, diethylene glycol monolaurate, C ₂ -C ₂₄ alcohol, C ₂ -C ₂₄ amine, polydimethylsiloxane-co-PEG, and combinations thereof. . In some embodiments, the additive is selected from the group consisting of decanol, ethoxyethanol, polydimethylsiloxane-co-PEG, and combinations thereof. In at least some embodiments, the additive can be interpreted as a substance other than the polymerized composition that is mixed with the polymerizable silicone hydrogel contact lens precursor composition during formation of the lens body.
Polydimethylsiloxane-co-PEG (PDMS-co-PEG) can be interpreted as a hydrophilic silicone-containing material, also referred to herein as silicone oil. These hydrophilic silicone materials are generally soluble in water and alcohol. Hydrophilic silicone-containing materials useful in the compositions and lens products of the present invention can be interpreted as compatibilizers. Further, such materials can be interpreted as mold release aids and de-lens aids. For example, a polymerized silicone hydrogel contact lens product made of a hydrophilic silicone-containing material can be selectively attached to and detached from a single mold member, such as a male mold member of a contact lens mold. Easy to lens. In addition, silicone oil reduces the water content in silicone hydrogel contact lenses, helps maintain wettability of silicone hydrogel contact lenses, and reduces ionoflux in contact lenses compared to lenses made from compositions without silicone oil. can do. Typically, the silicone oil provided in the present formulation and lens product has a molecular weight of less than about 3000 Daltons. For example, the silicone oil in the present compositions and products has a molecular weight of about 100 daltons to about 3000 daltons. In some embodiments, the silicone oil has a molecular weight of about 300 daltons to about 1000 daltons. In some specific embodiments, the silicone oil has a molecular weight of about 600 daltons and a non-siloxane content of about 75%. Silicone oil can be interpreted as a surfactant and can be interpreted as a substance having a silicon-containing skeleton linked to long PEG chains.

In another embodiment, the silicone hydrogel contact lens is a process that extracts extractable components from a polymerized silicone hydrogel contact lens product prior to extraction to produce an extracted polymerized silicone hydrogel contact lens product. Includes manufactured lens body. The extractable component is provided in an amount of at least 10% (w / w) of the polymerized silicone hydrogel contact lens product prior to extraction. The manufacturing process of the lens body further includes the step of hydrating the extracted polymerized silicone hydrogel contact lens product to produce a silicone hydrogel contact lens having an eye-acceptable surface wettability.
As discussed herein, the extractable component may be present in an amount from 10% to about 75% (w / w) of the polymerized silicone hydrogel contact lens product prior to extraction. Alternatively, the polymerized silicone hydrogel contact lens product prior to extraction can be interpreted as having an extractable component content of 10% to about 75% (w / w). For example, the extractable component may be present in an amount from about 15% to about 65% (w / w) of the polymerized silicone hydrogel contact lens product prior to extraction.
In certain embodiments, the extractable component of the polymerized silicone hydrogel contact lens product prior to extraction includes at least one removable additive as described herein. For example, the extractable component can include a compatibilizer, a mold release aid, a de-lens aid, a wettability enhancer, an ionoflux reducer, a modulus effect agent, and combinations thereof, as described herein.

The lens of a particular embodiment includes a lens body without surface treatment that provides acceptable surface wettability to the eye. In other words, the lens body of the silicone hydrogel contact lens is a non-surface-treated lens body. Alternatively, the lens body is manufactured without surface treatment of the lens body to provide acceptable surface wettability to the eye. For example, the lens body of the present lens embodiment does not include a plasma treatment or additional coating provided to make the surface of the lens body more acceptable to the eye. However, the lens has surface wettability that is acceptable to the eye, depending on the amount of removable material present in the polymerized silicone hydrogel contact lens product prior to extraction, so that it may optionally include a surface treatment. There may also be embodiments.
In addition, embodiments of the present lens include a lens body that is free of an interpenetrating polymer network of polymeric wetting agents that provides eye-acceptable surface wettability. In other words, the lens body of the present lens embodiment has an eye-acceptable surface wettability and does not include a polymer wetting agent IPN such as polyvinylpyrrolidone (PVP). For example, the lens body of the present lens is made without contacting the polymerizable silicone hydrogel contact lens precursor composition with a polymer wetting agent.

Particular embodiments of the lens include a lens body that is a cast molded element obtained from a non-polar resin contact lens mold. A polymerized silicone hydrogel contact lens product can be interpreted as a product polymerized or cured in a non-polar resin contact lens mold. Alternatively, the polymerized silicone hydrogel contact lens product is produced in a non-polar resin contact lens mold. As discussed herein, such contact lens molds are molds that are manufactured using or based on nonpolar or hydrophobic resin materials. Such materials typically have a relatively large contact angle on their lens forming surface. For example, a nonpolar resin or hydrophobic resin mold may have a contact angle greater than about 90 degrees. Examples of suitable nonpolar resin molds that can be used in the lenses of these embodiments include resin materials containing one or more polyolefins. Some examples of suitable resin materials include polyethylene, polypropylene, and polystyrene, and other materials that have similar hydrophobic properties. Nonpolar resin-based molds are not based on polar resins such as polyvinyl alcohol or ethylene vinyl alcohol copolymers.
In a further embodiment, the lens includes a lens body that includes a combination of the above features. For example, a silicone hydrogel contact lens may comprise a lens body without surface treatment and without the polymer wetting agent IPN. As another example, a silicone hydrogel contact lens may include a lens body that has no surface treatment, no polymer wetting agent IPN, and is a cast molded element obtained from a non-polar resin contact lens mold.

Some embodiments of the present silicone hydrogel contact lens include one or more comfort enhancers (in silicone hydrogel contact lenses without the enhancer) that enhance the comfort of the contact lens perceived by the lens wearer or group of lens wearers. To enhance comfort compared to). An example of a comfort enhancer that can be included in the present lens is a dehydration reducing agent. Another example of a comfort enhancer is a tear film stabilizer. Another example of a comfort enhancer is an agent that reduces dehydration and stabilizes the tear film of the eye on which the contact lens is placed. Comfort enhancers include polymeric materials that have an affinity for water. In certain embodiments, the polymeric material includes one or more amphiphilic groups. Examples of suitable materials include materials that contain a polymerizable phospholipid, such as a phosphorylcholine component. In some embodiments, the lens includes a lens body that includes units of methacrylate phosphorylcholine monomer. In a further embodiment, the lens comprises 2-methacryloyloxyethyl phosphorylcholine (MPC). MPC can be obtained from companies such as Biocompatibles Limited (Great Britain) and NOF Corporation (Tokyo, Japan) or can be produced as described in US Pat. Nos. 5,981,786; 6,420,453; and 6,423,761.
As discussed herein, the comfort of the silicone hydrogel lens is enhanced by including one or more removable comfort enhancers in the lens precursor composition and the silicone hydrogel contact lens product prior to extraction. You can also. For example, some of the removable materials described herein include agents that reduce the ionoflux of the lens compared to lenses obtained from the same composition without the removable material. Reducing the ionoflux of the lens can help reduce lens wearer's cornea dehydration and reduce corneal staining caused by lens wear.
As discussed herein, the lens has features and characteristics that allow the wearer to wear the lens for extended periods of time. For example, this lens can be worn as a daily wear lens, a 1 week wear lens, a 2 week wear lens, or a 1 month wear lens. The lens includes a hydrated lens body having surface wettability, modulus, ionoflux, oxygen permeability, and moisture content that contributes to the comfort and usefulness of the lens. In certain embodiments, the lens has an advancing contact angle less than about 95 degrees, a tensile modulus less than about 1.6 MPa, an ionoflux less than about 7 × 10 ⁻³ mm ² / min, at least about 5.25035 × 10 ⁻¹⁶ m. Includes a hydrated lens body having characteristics selected from the group consisting of oxygen permeability (Dk) of ² · s ⁻¹ · Pa ⁻¹ (70 barr ), water content of at least about 30% by weight, and combinations thereof . However, in other embodiments, the ionoflux may be greater than 7 × 10 ⁻³ mm ² / min and still does not cause corneal dehydration staining or other clinical problems. For example, if the silicone hydrogel contact lens includes a comfort enhancer such as a phosphorylcholine component, such as MPC, the ionoflux can be about 25 × 0 ⁻³ mm ² / min, but is still clinically acceptable.
The lens may include a hydrated lens body having an anterior contact angle of less than 120 degrees, front, back, or front and back. In certain embodiments, the lens body has a lens surface advancing contact angle of less than 90 degrees, for example, the lens body is about 85 degrees, about 80 degrees, about 75 degrees, about 70 degrees, about 65 degrees, A lens surface advancing contact angle of about 60 degrees, about 55 degrees, or about 50 degrees. The lens body may have a receding contact angle of the lens surface of less than 80 degrees, for example, the lens body is about 75 degrees, about 70 degrees, about 65 degrees, about 60 degrees, about 55 degrees, about 50 degrees, Or it may have a receding contact angle of the lens surface of about 45 degrees. The hysteresis, i.e. the difference between the advancing contact angle and the receding contact angle, may be about 5 degrees to about 35 degrees. However, in certain embodiments, the hysteresis is greater than 25 degrees and may still be clinically acceptable. For example, if the silicone hydrogel contact lens includes a comfort enhancer such as a phosphorylcholine component, eg, MPC, the hysteresis can be about 60 degrees, but is still clinically acceptable.
The advancing contact angle can be determined by routine methods known to those skilled in the art. For example, the advancing and receding contact angles of a contact lens can be measured using conventional drop shape methods, such as the sessile drop method or captive bubble method. The Kruss DSA 100 instrument (Kruss GmbH, Hamburg) can be used to determine the advancing and receding contact angles of silicone hydrogel contact lenses as described in the following literature (DA Brandreth: "Dynamic contact angles and contact angle hysteresis ", Journal of Colloid and Interface Science, vol. 62, 1977, pp. 205-212 and R. Knapikowski, M. Kudra: Kontaktwinkelmessungen nach dem Wilhelmy-Prinzip-Ein statistischer Ansatz zur Fehierbeurteilung", Chem. Technik , vol. 45, 1993, pp. 179-185, and US Pat. No. 6,436,481).
As an example, the advancing contact angle and the receding contact angle can be determined by a captive bubble method using phosphate buffered saline (PBS; pH = 7.2). Prior to testing, the lens is flattened on a quartz surface and rehydrated with PBS for 10 minutes. An air bubble is placed on the surface of the lens using an automatic injection system. By increasing or decreasing the air bubble size, a receding angle (a plateau obtained when the bubble size is increased) and an advancing angle (a plateau obtained when the bubble size is reduced) can be obtained.
The lens may additionally or alternatively include a lens body that exhibits a water break-up time (BUT) greater than 5 seconds. For example, embodiments of the present lens comprising a lens body having a BUT of water for at least 15 seconds, such as 20 seconds or more, may have surface wettability acceptable to the eye.
The lens may include a lens body having a modulus less than 1.6 MPa. In certain embodiments, the modulus of the lens body is less than 1.0 MPa. For example, the lens body can have a modulus of about 0.9 MPa, about 0.8 MPa, about 0.7 MPa, about 0.6 MPa, about 0.5 MPa, about 0.4 MPa, or about 0.3 MPa. An example of the silicone hydrogel contact lens has a modulus of about 0.55 MPa. The modulus of the lens body is selected to provide a comfortable lens when placed on the eye and to accommodate lens handling by the lens wearer.
Routine methods known to those skilled in the art can be used to determine the modulus of the lens body. For example, a contact lens piece of about 4 mm width is cut out from the center of the lens and obtained by a tensile test using Instron 3342 (Instron Corporation) at a rate of 10 mm / min in air at 25 ° C. and at least 75% humidity. The tensile modulus (unit: MPa) can be determined from the initial slope of the resulting stress-strain curve.

The ionoflux of the lens body of the lens can be less than about 5 × 10 ⁻³ mm ² / min. Some lens bodies of this lens may have an ionoflux up to about 7 × 10 ⁻³ mm ² / min, but the ionoflux is less than about 5 × 10 ⁻³ mm ² / min and the contact lens is When MPC is not included, it is thought that dehydration staining of the cornea can be reduced. In certain embodiments, the ion flux of the lens body is about 4.5 × 10 ⁻³ mm ² / min, about 4 × 10 ⁻³ mm ² / min, about 3.5 × 10 ⁻³ mm ² / min, about 3 × 10 ^−3. mm ² / min or less. However, as described herein, the ionoflux may be greater than 7 × 10 ⁻³ mm ² / min and still does not cause corneal dehydration staining or other clinical problems. For example, if the silicone hydrogel contact lens includes a comfort enhancer such as a phosphorylcholine component, eg, MPC, the ionoflux can be about 25 × 10 ⁻³ mm ² / min, but is still clinically acceptable.
Routine methods known to those skilled in the art can be used to determine the ionoflux of the lens body of the lens. For example, the ionoflux of a contact lens or lens body can be measured using a technique substantially similar to the “ionoflux technique” described in US Pat. No. 5,849,811. For example, the lens to be measured can be placed in a lens holding device between the male part and the female part. The male and female portions include a lens and a flexible sealing ring positioned between the respective male and female portions. After positioning the lens in the lens holding device, the lens holding device is placed in a threaded lid. The lid is screwed onto the glass tube to define the donor chamber. The donor chamber can be filled with 16 ml of 0.1 molar NaCl solution. The receiving chamber can be filled with 80 ml of deionized water. Receive a conductivity meter lead and immerse it in deionized water in the chamber, and add a stir bar to the chamber. Place the receiving chamber in a thermostat and keep the temperature at about 35 ° C. Finally, the donor chamber is dipped into the receiving chamber. Beginning 10 minutes after immersion in the receiving chamber of the donor chamber, conductivity measurements can be taken every 2 minutes for about 20 minutes. The conductivity versus time data will be substantially linear.
The lens body of this lens typically has high oxygen permeability. For example, the lens body has a Dk oxygen permeability of no less than 60 barrers. Embodiments of the present lens include a lens body having a Dk of about 80 barrer , about 90 barrer , about 100 barrer , about 110 barrer , about 120 barrer , about 130 barrer , about 140 barrer or more.
Routine methods known to those skilled in the art can be used to determine the Dk of the lens. For example, the Dk value can be determined using the Mocon method as described in US Pat. No. 5,817,924. The Dk value can be determined using commercially available equipment under the Mocon Ox-Tran System model selection.
The lens also includes a lens body having a water content acceptable to the eye. For example, embodiments of the present lens include a lens body having a moisture content no less than 30%. In some embodiments, the lens body has a moisture content of about 35%, about 40%, about 45%, about 50%, about 55%, about 60%, or about 65%.
The water content of the lens can be determined using routine methods known to those skilled in the art. For example, a hydrated silicone hydrogel contact lens can be removed from the aqueous liquid and wiped to remove excess water on the surface and weighed. The dried lens can be weighed after the weighed lens is dried in an oven at 80 ° C. under vacuum. The weight difference can be determined by subtracting the weight of the dry lens from the weight of the hydrated lens. The water content (%) is (weight difference / hydrated weight) × 100.

In addition to the unique values identified above, the lens may have a range of values between any combination of the unique values identified above. For example, the contact lens has a moisture content of about 45% to about 55%, an ionoflux value of about 3.9 to about 5.3, a static contact angle of about 35 degrees to about 45 degrees, and a forward contact of about 55 degrees to about 75 degrees. Angle, a receding contact angle of about 47 to about 55 degrees, a hysteresis of about 11 degrees to about 25 degrees, a Young modulus of about 0.47 MPa to about 0.51 MPa, an elongation of about 140% to about 245%, and combinations thereof Can do.
In some specific embodiments of the present silicone hydrogel contact lens, the lens body has a BUT of water for more than 20 seconds, a modulus of less than 0.5 MPa, an ionoflux of less than 5, and a moisture content of about 55%.
The silicone hydrogel contact lens is a vision correction or vision enhancement contact lens. The lens may be a spherical lens or an aspheric lens. The lens may be a multifocal lens such as a single focus lens or a bifocal lens. In some embodiments, the lens is a rotationally stabilized lens, such as a rotationally stabilized toric contact lens. The rotationally stabilized contact lens may be a contact lens that includes a lens body that includes a ballast. For example, the lens body may have prism ballast, peri ballast, and / or one or more thinned upper and lower regions.
The lens also includes a lens body that includes a peripheral region. The peripheral region may include a rounded portion. For example, the peripheral region may include a rounded trailing edge surface, a rounded leading edge surface, or a combination thereof. In certain embodiments, the periphery is completely rounded from the front surface to the rear surface. Therefore, it can be interpreted that the lens body of the present lens can include a rounded periphery.

The lens addresses the problems associated with existing silicone hydrogel contact lenses, but may still include a lens body with a thickness profile that is comfortable for the lens wearer. The rigidity of the lens body can be adjusted by changing the thickness of the lens body and the modulus of the lens body. For example, the stiffness of a region of a contact lens is defined as the product of the lens Young's modulus and the square of the lens thickness in the specified region. Thus, certain embodiments of the present lens have a center stiffness of less than about 0.007 MPa-mm ² (e.g., a stiffness at the center of the lens or the center of the visual zone), a stiffness of the lens nucleus junction less than about 0.03 MPa-mm ^2. Or a combination thereof. The lens nucleus junction is defined as the junction between the lens nucleus zone and the bevel, or for a lens without a bevel, a point approximately 1.2 mm from the lens edge (see US Pat. No. 6,849,671). In other embodiments, the present lenses may comprise higher center rigidity than 0.007 MPa-mm ^2, the rigidity of about 0.03 MPa-mm ² higher lenticular junction, or a combination thereof.

The silicone hydrogel contact lenses have little variability in physical parameters such as physical dimensions between lenses or lens batches. For example, in certain embodiments, additives can be added to the polymerizable silicone hydrogel contact lens precursor composition to reduce the variability of the physical attributes of the lens. With such physical parameter adjusting additives, the variability between any two batches of lenses can be less than 2%. For example, the variability of one or more batches of the lens may be from about 0.5% to about 1.9%. For example, the diameter and base curve of the lens can be adjusted within 1.6% of a predetermined value. More specifically, if the target contact lens diameter is 14.0 mm and the actual diameter of the contact lens in the batch of contact lenses varies from about 13.6 mm to about 14.4 mm, one or more during contact lens manufacture Can be used to produce contact lenses having a diameter in the range of about 13.8 mm to about 14.2 mm with reduced variability. Similar adjustments can be made to reduce changes in lens thickness, sagittal depth, basic curvature, and the like. The additive may be a diluent or compatibilizer and may be supplied in an amount up to about 5% (w / w). Thus, the addition of diluents or other additives can help to reduce or adjust the distortion between the present contact lenses. In addition, changing the active or reactive components present in the polymerizable composition as well as diluents or additives may target physical properties such as lens modulus between different batches of lenses. Can be helpful.
The silicone hydrogel contact lens may be provided in a sealed package. For example, the silicone hydrogel contact lens may be provided in a sealed blister pack or other similar container suitable for delivery to a lens wearer. Within the package, the lens may be stored in an aqueous solution such as saline. Some suitable solutions include phosphate buffered saline and borate buffer. The solution may optionally include a bactericidal agent or may be free of a bactericidal or preservative. The solution may optionally contain a surfactant such as poloxamer.
The lens in the sealed package is preferably sterile. For example, the lens may be sterilized before sealing the package, or it can be sterilized in a sealed package. The sterile lens may be a lens exposed to a sterilizing amount of radiation. For example, the lens may be an autoclaved lens, a gamma irradiated lens, a lens exposed to ultraviolet light, and the like.

Another aspect of the invention relates to a polymerized silicone hydrogel contact lens product prior to extraction. For example, it relates to a lens product that has been polymerized but not subjected to an extraction procedure, as described herein.
As described above, when a pre-extracted polymerized silicone hydrogel contact lens product having a relatively high amount of removable material, such as extractables, is produced, the lens is made using a non-polar resin contact lens mold. And provides a silicone hydrogel contact lens with surface wettability that is acceptable to the eye, even when the surface treatment of the polymeric wetting agent IPN is not included.
The embodiment of the polymerized silicone hydrogel contact lens product before extraction of the present invention is based on the dry weight of the body member after forming the polymerized silicone hydrogel contact lens product extracted by subjecting the body member to an extraction procedure. Including a body member before extraction having a dry weight of at least 10% greater. For example, the polymerized silicone hydrogel contact lens product prior to extraction has an extractable component content of at least 10% (w / w) of the lens product. In some embodiments, the polymerized silicone hydrogel contact lens product prior to extraction has an extractable component content that does not exceed 75% of the lens product. In a further embodiment, the extractable component content is about 15% to about 65% (w / w) of the extracted lens product. In a further embodiment, the extractable component content is about 15% to about 50% (w / w) of the extracted lens product.
Since the lens is obtained from a non-polar resin contact lens mold, an embodiment of the pre-extracted silicone hydrogel contact lens product of the present invention is provided in contact with the non-polar resin contact lens mold. Such products. For example, one embodiment is a pre-extracted product provided in a closed contact lens mold or a pre-extracted product provided on one mold member of a released contact lens mold. Good. In some embodiments, the lens product prior to extraction is in contact with the male contact lens mold member.
Embodiments of the pre-extracted silicone hydrogel contact lens product of the present invention also include a body member that includes one or more removable additives, such as non-reactive additives. Additives include each of the above-described additives and all additives, and combinations of these additives are also included. Thus, the lens product before extraction is selected from the group consisting of compatibilizers, mold release aids, de-lens aids, wettability enhancers, ionoflux reducers, comfort agents, and combinations thereof. It can be interpreted that the above additives may be included.
In some embodiments, the lens product comprises a body member prior to extraction that includes units of a methacrylate phosphorylcholine-monomer such as 2-methacryloyloxyethyl phosphorylcholine.

Another aspect of the invention relates to a polymerizable silicone hydrogel contact lens precursor composition. The precursor composition of the present invention may comprise a polymerizable silicon-containing component and a polymerizable non-silicon-containing component. These two components are formulated as a polymerizable silicone hydrogel contact lens precursor composition. A portion of the precursor composition can be removed from the polymerized silicone hydrogel contact lens product produced from the precursor composition. This portion that can be removed is present in an amount of at least 10% (w / w) of the polymerized silicone hydrogel contact lens product.
In certain embodiments, the non-silicon-containing component of the precursor composition comprises a first monomer having a first reactivity ratio and a second monomer having a second reactivity ratio that is less than the first reactivity ratio. Including. For example, if the first monomer has a reactivity ratio of about 3, the second monomer has a reactivity ratio of less than about 3. The second reactivity ratio is less than about 10%, less than about 20%, less than about 30%, less than about 40%, less than about 50%, less than about 60%, less than about 70% of the first reactivity ratio, It can be less than about 80%, or less than about 90%. In some embodiments, the second monomer has a reactivity ratio of 0.5 and the first monomer has a reactivity ratio of 3. The lens product and lens of the present invention can be manufactured using reactive components with different reactivity ratios during the formation of the polymerization product. Since the higher reactivity ratio component is usually more reactive than the lower reactivity ratio component, the first monomer with the higher reactivity ratio will react more in a given time. In some embodiments, the precursor composition also includes a crosslinker having a reactivity ratio that is comparable to the first reactivity ratio than the second reactivity ratio. Accordingly, the type of reactive component in the precursor composition of the present invention affects the amount of removable component present in the polymerized lens product, the dry weight of the silicone hydrogel contact lens, and the wettability of the lens. obtain.

Further, the precursor composition of the present invention may include one or more initiators. A thermal initiator can be interpreted as having a “kick-off” temperature. By selecting a thermal initiator with a higher kick-off temperature, and by using a relatively low amount of initiator, the ionoflux of the lens can be reduced and the removable components described herein Can affect the amount of. For example, one thermal initiator used in the precursor composition of the present invention is a 2,2′-azobis (2,4- Dimethylpentanenitrile) (VAZO-52). The second thermal initiator used in the precursor composition of the present invention is azo-bis-isobutyronitrile (VAZO-88) having a kick-off temperature of about 90 ° C. Eye-compatible silicone hydrogel contact lenses can be obtained from precursor compositions containing about 0.2 parts VAZO-52 or about 0.1 parts VAZO-88. Further, the curing methods disclosed herein for polymerizing polymerizable compositions can include one or more temperature steps.
Embodiments of the precursor composition of the present invention may include one or more removable or extractable hydrophobic or amphiphilic additives, such as the specific additives described above. The one or more additives may be present in an amount from about 1% to about 60% (w / w). In some embodiments, one or more additives are present in an amount from about 30% (w / w) to about 60% (w / w). In some compositions, at least two different additives are provided.

Specific embodiments of the precursor composition of the present invention include polymerizable silicone hydrogel contact lens precursor compositions supplied in non-polar resin contact lens molds. Other embodiments include the composition in a storage container such as a bottle, or a dispensing device such as a manual or automatic pipetting device.
An example of a precursor composition of the present invention is a dimethacryloyl silicone-containing macromer, α-ω-bis (methacryloyloxyethyliminocarboxyethyloxypropyl) -poly (dimethylsiloxane) -poly (trifluoropropylmethylsiloxane) -poly (ω A polymerizable silicon-containing component consisting of -methoxy-poly (ethylene glycol) propylmethylsiloxane) (M3U) and N-vinyl-N-methylacetamide (VMA), isobornyl methacrylate (IBM), ethoxyethyl methacrylate (EOEMA) ), Tri (ethylene glycol) dimethacrylate (TEGDMA), triethylene glycol divinyl ether (TEGDVE), and 2,2'-azobis (2,4-dimethylpentanenitrile) (VAZO-52) Containing ingredients. The IBM in this composition appears to increase the stiffness of the extracted silicone hydrogel contact lens compared to a substantially identical lens without IBM. The silicon-containing component can comprise about 30 to about 40% (w / w) of the composition, and the non-silicon-containing component can comprise about 60 to about 70% (w / w) of the composition. . In one embodiment, M3U is supplied in an amount of about 30 to about 40%, VMA is supplied in an amount of about 45 to about 50%, MMA is supplied in an amount of about 15 to about 20%, and IBM is about It is supplied in an amount of 5%, EOEMA is supplied in an amount of 15%, TEGDMA or TEGDMA and TEGDVE are supplied in an amount of about 0.2%, and VAZO-52 is supplied in an amount of about 0.5%.
Another example of a precursor composition of the present invention comprises the above components, an ultraviolet absorber and a colorant (which may be a reactive dye or pigment particle). The UV absorber may be supplied in an amount of about 0.9% and the colorant may be supplied in an amount of about 0.1%. The UV absorber may be a strong UV absorber that exhibits a relatively high absorption value in the UV-A range of about 320-380 nm, but is relatively transparent at about 380 nm. For example, photopolymerizable hydroxybenzophenone as a UV absorber and photopolymerizable benzotriazole, such as 2-hydroxy-4-acryloyloxyethoxybenzophenone (commercially available from Cytec Industries as CYASORB® UV416), 2 -Hydroxy-4- (2-hydroxy-3-methacrylyloxy) propoxybenzophenone, and photopolymerizable benzotriazole commercially available from Noramco as NORBLOC® 7966. Other photopolymerizable UV absorbers include polymerizable ethylenically unsaturated triazines, salicylates, aryl-substituted acrylates, polymerizable versions of other useful UV absorbers, and mixtures of these UV absorbers.

Another embodiment of the precursor composition of the present invention comprises a polymerizable silicon-containing component comprising M3U and a polymerizable non-silicon-containing component comprising VMA, methyl methacrylate (MMA), TEGDMA, and VAZO-52. .
Further examples of the precursor composition of the present invention include the components of the previous embodiments, UV absorbers and colorants. This embodiment may also include a block copolymer of polydimethylsiloxane (PDMS) and polyethylene glycol (PEG). In this specification, this block copolymer is abbreviated as PDMS-co-PEG. An example of DMS-co-PEG has a PEG content of 75% and a molecular weight of about 1400. Another example of a useful PDMS-co-PEG material has a molecular weight of about 300 to about 3000 daltons. PDMS-co-PEG may be present in an amount from about 10% (w / w) to about 40% (w / w). For example, the precursor composition may be in an amount of 12% (w / w), 20% (w / w), 25% (w / w), 29% (w / w), or 30% (w / w). PDMS-co-PEG may be included.
Another embodiment of the precursor composition of the present invention is a polymerizable non-silicon comprising a polymerizable silicon-containing component comprising M3U and VMA, IBM, MMA, TEGDMA, UV absorber, colorant, and VAZO-64. Containing ingredients. Embodiments of these compositions can have a higher modulus than the other embodiments disclosed herein.
Another embodiment of the precursor composition of the present invention is a polymerizable non-silicon comprising a polymerizable silicon-containing component comprising M3U and 1-vinyl-2-pyrrolidone (NVP), MMA, TEGDMA, and VAZO-52. Containing ingredients. In such embodiments, the silicon-containing component comprises about 30 to about 40% (w / w) of the composition, and the non-silicon-containing component is about 60 to about 70% (w / w) of the composition. Configure w). For example, M3U may be present in an amount from about 35% to about 38%. NVP is present in an amount of about 45 to about 50%, MMA is present in an amount of about 15 to about 20%, TEGDMA is present in an amount of about 0.1 to about 0.8%, and VAZO-52 is about 0.1 to about It can be present in an amount of 0.6%.
Another embodiment includes the same ingredients and decanol as before. Decanol can be supplied in an amount of about 5% (w / w) to about 30% (w / w). For example, embodiments have about 5% (w / w), about 10% (w / w), about 15% (w / w), about 20% (w / w), about 25% (w / w) Or about 30% (w / w) of decanol. Decanol can be effective as both a compatibilizer and a diluent. Thus, decanol can help reduce phase separation of the components of the lens precursor composition. One specific example of a decanol-containing formulation is 35% M3U, about 45% to about 55% NVP, about 13% to about 20% MMA, about 0.1% TEGDMA, about 0.6% (VAZO-52), And about 30% or less of decanol.
The NVP-containing precursor composition may also include a release aid, such as a release aid that includes a hydrophilic silicone component, a polyalkylene oxide component, or a combination thereof.
The present NVP-containing precursor composition may also include a diluent selected from the group consisting of hexanol, ethoxyethanol, isopropanol (IPA), propanol, decanol, silicone oil, and combinations thereof. The diluent can be present in an amount of about 10% to about 30% (w / w). A composition with a relatively high concentration of diluent appears to have a lower ionoflux value, a reduced modulus, an increased elongation, and a BUT of water longer than 20 seconds.
The diluent-containing NVP-containing precursor composition comprises units of methacrylate phosphorylcholine-monomer, such as 2-methacryloyloxyethyl phosphorylcholine. MPC may be present in an amount from about 1% (w / w) to about 15% (w / w) of the composition. For example, if the composition comprises about 2.5% MPC, about 5% MPC, about 7% MPC, about 10% MPC, or about 12% MPC, a silicone hydrogel contact lens that is compatible with the eye. Can be manufactured. The composition may include an alcohol-based diluent.
For example, some compositions contain about 5% decanol.
Embodiments of the present NVP-containing composition, including the embodiments described above, also include (3-methacryloxy-2-hydroxypropyloxy) propylbis (trimethylsiloxy) methylsilane (SiGMA).

Another aspect of the present invention relates to a method for producing a silicone hydrogel contact lens.
In certain embodiments, the method comprises the step of extracting the body of the lens prior to extraction from the silicone hydrogel contact lens product prior to extraction (having a removable component content of at least 10% (w / w) of the lens product). Forming a silicone hydrogel contact lens body having a dry weight not exceeding 90% of the dry weight and having an eye-acceptable surface wettability.
The forming step of the method can include extracting an extractable from the pre-extracted silicone hydrogel contact lens product.
The method cures a polymerizable silicone hydrogel contact lens precursor composition and removes the polymerized silicone hydrogel contact lens product (at least 10% (w / w) of the lens product) prior to extraction. A step of forming a content). As discussed herein, the curing process may be heat curing or ultraviolet curing. Curing can occur in non-polar resin contact lens molds, such as polyolefin-based contact lens molds.
The method can include combining a polymerizable silicon-containing component and a polymerizable non-silicon-containing component to form a polymerizable silicone hydrogel contact lens precursor composition. Embodiments of this method may include the step of adding a removable additive to the polymerizable silicone hydrogel contact lens precursor composition. Additives may be added to the final monomer mixture, or additives may be added to either the silicon-containing component or the non-silicon-containing component prior to mixing the two components. The additive may be any additive described herein, or a combination of the additives.
The method may include adding an ultraviolet absorber, a colorant, and combinations thereof to the lens precursor composition. As is apparent from the above description, the method is carried out without surface treatment of the lens, without forming a lens with the polymer wetting agent IPN, without using a polar resin mold, or a combination thereof. Without it, silicone hydrogel contact lenses can be manufactured.

In view of the disclosure herein, embodiments of the present silicone hydrogel contact lenses are subject to an extraction procedure, from a polymerizable silicone hydrogel contact lens precursor composition, to a polypropylene molded nitrogen cured polymerized silicone hydrogel contact lens. Efficient removal of extractables from the product (wet-enhancing monomer, compatibilizing amount of one or more additives, and high amounts of extractables are distributed throughout the composition and the lens product) Can be interpreted as including a lens body. This lens body has surface wettability that is acceptable to the eye.
Using the present compositions and methods, problems associated with the use of polar resin molds, such as difficulty in separating mold halves upon polymerization; problems with elaborate and expensive post-polymerization procedures such as plasma etching, irradiation Invented a silicone hydrogel contact lens that was ocularly compatible, while avoiding the problems associated with chemical modification; and the polymer wetting agent IPN.

〔Example〕
The following examples illustrate certain aspects and advantages of the present invention, which should not be construed as limiting the invention.
The examples refer to the following well-known chemicals, but sometimes they are also represented by the abbreviations shown below.
PP: Propylene
PEG: Polyethylene glycol
IBM: Isobornyl methacrylate
VMA: N-vinyl-N-methylacetamide (freshly distilled under vacuum)
M3U: M3-U; α-ω-bis (methacryloyloxyethyliminocarboxyethyloxypropyl) -poly (dimethylsiloxane) -poly (trifluoropropylmethylsiloxane) -poly (ω-methoxy-poly (ethylene glycol) propylmethyl Siloxane); dimethacryloyl silicone-containing macromer M3U used in the following examples is represented by the following formula, where n is 121, m is 7.6, h is 4.4, Mn = 12,800, and Mw = 16,200.

EOENA: Ethoxyethyl methacrylamide
VAZO-52: 2,2'-azobis (2,4-dimethylpentanenitrile) (V-52; thermal initiator)
VAZO-64: Azo-bis-isobutyronitrile (V-64; thermal initiator)
PDMS: Polydimethylsiloxane
PDMS-co-PEG: Block copolymer of polydimethylsiloxane and PEG containing 75% PEG, 600 MW (Gelest's DBE712)
HEMA: 2-hydroxyethyl methacrylate
NVP: 1-vinyl-2-pyrrolidone (freshly distilled under vacuum)
HOB: 2-hydroxylbutyl methacrylate
FM0411M: FM-0411M; methacryloyloxyethyliminocarboxyethyloxypropyl-poly (dimethylsiloxy) -butyldimethylsilane
FM0411M: The one used in the following examples is represented by the following formula, where n = 13 to 16 and Mw is 1500.

TAIC: 1,3,5-triallyl-1,3,5-triazine-2,4,6 (1H, 3H, 5H) -trione (triallyl isocyanurate)
AOT: Aerosol OT; Bis (2-ethylhexyl) sulfosuccinic acid sodium salt
TPO: Biphenyl (2,4,6-trimethylbenzoyl) phosphine oxide
IPA: Isopropyl alcohol
N, N-DMF: DMF; N, N-dimethylformamide
HMP: 4-hydroxy-4-methyl-2-pentanone
TEGDMA: Triethylene glycol dimethacrylate
TEGDVE: Triethylene glycol divinyl ether
MMA: Methyl methacrylate
VM: Vinyl methacrylate
PTA: Pentaerythritol triacrylate
TPTMA: Trimethylolpropane trimethacrylate
SiGMA: (3-Methacryloxy-2-hydroxypropyloxy) propylbis (trimethylsiloxy) methylsilane
Pr: Propanol
Hx: Hexanol
DA: Decanol
DVG: Divinyl glycol
EE: Ethoxyethanol
UV416: 2- (4-benzoyl-3-hydroxyphenoxy) ethyl acrylate
M3U Tint: A dispersion of βCu-phthalocyanine in M3U (% w / w). Cu-phthalocyanine is available from BASF as Heliogen Blue K7090.

Example 1
Silicone hydrogel contact lens fabrication:
The compounds shown in Examples 2-55 were weighed and mixed to form a mixture. The mixture was filtered through a 0.2-5.0 micron syringe filter into a bottle. The mixture was stored for up to about 2 weeks. This mixture is interpreted as a polymerizable silicone hydrogel contact lens precursor composition. In Examples 2 to 55, the unit weight was given in addition to the respective weight percent of each compound (expressed in terms of weight on a weight basis; w / w). In the final silicone hydrogel contact lens, the weight percent of the compound is closely related to the unit amount present in the precursor composition.
A volume of the precursor composition was placed in contact with the lens-defining surface of a female non-polar resin mold member, such as a polypropylene mold member. A male mold member of nonpolar resin, for example, a polypropylene male mold member, was placed in contact with the female mold member to form a contact lens mold comprising a contact lens shaped cavity containing the precursor composition.
The contact lens mold was placed in a nitrogen flushed oven to thermally cure the precursor composition. The contact lens mold was exposed to a temperature of about 80 ° C. for about 1 hour or longer.
After polymerization of the precursor composition, the contact lens mold was released and the polymerized silicone hydrogel contact lens product prior to extraction was de-lensed from one of the mold members. The unlensed lens product before extraction was weighed to determine its dry weight.
The delensed lens product was extracted and hydrated by contacting the lens product with multiple volumes of alcohol (eg, ethanol) and deionized water. The hydrated silicone hydrogel contact lens was weighed and then dehydrated in an oven, and the dry weight of the dehydrated silicone hydrogel contact lens was weighed again.
As described herein, properties such as contact angle (including dynamic and static contact angles), oxygen permeability, ion flux, modulus, elongation, tensile strength, moisture content, etc. were determined. The wettability of the hydrated silicone hydrogel contact lens was also examined by measuring the water break-up time. Eye compatibility was further examined during a dispensing study in which contact lenses were placed in human eyes for 1 hour, 3 hours, or more than 6 hours before clinical evaluation.

(Example 2)
Polymerizable silicone hydrogel contact lens precursor compositions were obtained by mixing and filtering the following specified amounts of compounds and as described in Example 1.

  Silicone hydrogel contact lenses obtained from this formulation were relatively easy to process and had acceptable compatibility. These contact lenses have an equilibrium water content of about 54%, a BUT of water longer than 20 seconds, a static contact angle of about 48 °, an ion flux of about 3.8, a Young modulus of about 0.5 MPa, and an elongation of about 227%. Had. These silicone hydrogel contact lenses had an extractable amount of 16.9 ± 0.3%.

Example 3
Polymerizable silicone hydrogel contact lens precursor compositions were obtained by mixing and filtering the following specified amounts of compounds and as described in Example 1.

  Silicone hydrogel contact lenses obtained from this formulation were relatively easy to process and had acceptable compatibility. These contact lenses have an equilibrium water content of about 54%, a BUT of water longer than 30 seconds, a static contact angle of about 34 °, an advancing contact angle of about 78 °, a receding contact angle of about 48 °, and an ion flux of about 6. A Young's modulus of about 0.7 MPa, and an elongation of about 186%. These silicone hydrogel contact lenses had an extractable amount of 17.5 ± 0.5%.

(Example 4)
Polymerizable silicone hydrogel contact lens precursor compositions were obtained by mixing and filtering the following specified amounts of compounds and as described in Example 1.

  Silicone hydrogel contact lenses obtained from this formulation were relatively easy to process and were compatible with mPC. These contact lenses have an equilibrium water content of about 25%, a BUT of water longer than 18 seconds, a static contact angle of about 36 °, an advancing contact angle of about 76 °, a receding contact angle of about 49 °, and an ion flux of about 6. A Young's modulus of about 0.7 MPa, and an elongation of about 167%.

Example 5
Polymerizable silicone hydrogel contact lens precursor compositions were obtained by mixing and filtering the following specified amounts of compounds and as described in Example 1.

  Silicone hydrogel contact lenses obtained from this formulation were relatively easy to process and were compatible with mPC. These contact lenses have an equilibrium water content of about 54%, a BUT of water longer than 20 seconds, a static contact angle of about 37 °, an advancing contact angle of about 76 °, a receding contact angle of about 48 °, and an ion flux of about 3.5. And a Young's modulus of about 0.6 MPa and an elongation of about 304%.

Example 6
Polymerizable silicone hydrogel contact lens precursor compositions were obtained by mixing and filtering the following specified amounts of compounds and as described in Example 1.

  Silicone hydrogel contact lenses obtained from this formulation exhibited acceptable mold release and delensability. These contact lenses have an equilibrium water content of about 53%, a BUT of water longer than 20 seconds, a static contact angle of about 34 °, an ion flux of about 5, a Young's modulus of about 0.4 MPa, and an elongation of about 197%. Had.

Example 7
Polymerizable silicone hydrogel contact lens precursor compositions were obtained by mixing and filtering the following specified amounts of compounds and as described in Example 1.

  Silicone hydrogel contact lenses obtained from this formulation had a modulus of about 0.6 MPa to about 0.9 MPa.

(Example 8)
Polymerizable silicone hydrogel contact lens precursor compositions were obtained by mixing and filtering the following specified amounts of compounds and as described in Example 1.

  Silicone hydrogel contact lenses obtained from this formulation had eye-acceptable surface wettability. These contact lenses have an equilibrium water content of about 52%, a BUT of water longer than 20 seconds, a static contact angle of about 42 °, an advancing contact angle of about 73 °, a receding contact angle of about 48 °, and an ion flux of about 3.9. A Young's modulus of about 0.5 MPa, and an elongation of about 242%. These silicone hydrogel contact lenses had an extractable amount of 43.4 ± 3.1%.

Example 9
Polymerizable silicone hydrogel contact lens precursor compositions were obtained by mixing and filtering the following specified amounts of compounds and as described in Example 1.

  The pre-extracted polymerized silicone hydrogel contact lens product obtained from this formulation had an extractable component content of about 26%. Silicone hydrogel contact lenses obtained from this formulation had eye-acceptable surface wettability.

Example 10
Polymerizable silicone hydrogel contact lens precursor compositions were obtained by mixing and filtering the following specified amounts of compounds and as described in Example 1.

  Silicone hydrogel contact lenses obtained from this formulation had eye-acceptable surface wettability.

Example 11
Polymerizable silicone hydrogel contact lens precursor compositions were obtained by mixing and filtering the following specified amounts of compounds and as described in Example 1.

  Silicone hydrogel contact lenses obtained from this formulation had eye-acceptable surface wettability.

Example 12
Polymerizable silicone hydrogel contact lens precursor compositions were obtained by mixing and filtering the following specified amounts of compounds and as described in Example 1.

  Silicone hydrogel contact lenses obtained from this formulation had eye-acceptable surface wettability.

Example 13
Polymerizable silicone hydrogel contact lens precursor compositions were obtained by mixing and filtering the following specified amounts of compounds and as described in Example 1.

  The pre-extracted polymerized silicone hydrogel contact lens product obtained from this formulation had an extractable component content of about 17%.

Example 14
Polymerizable silicone hydrogel contact lens precursor compositions were obtained by mixing and filtering the following specified amounts of compounds and as described in Example 1.

  The pre-extracted polymerized silicone hydrogel contact lens product obtained from this formulation had an extractable component content of about 36%. Silicone hydrogel contact lenses obtained from this formulation had eye-acceptable surface wettability.

Example 15
Polymerizable silicone hydrogel contact lens precursor compositions were obtained by mixing and filtering the following specified amounts of compounds and as described in Example 1.

  Silicone hydrogel contact lenses obtained from this formulation showed a water BUT longer than 20 seconds.

Example 16
Polymerizable silicone hydrogel contact lens precursor compositions were obtained by mixing and filtering the following specified amounts of compounds and as described in Example 1.

  Silicone hydrogel contact lenses obtained from this formulation showed a water BUT longer than 20 seconds.

Example 17
Polymerizable silicone hydrogel contact lens precursor compositions were obtained by mixing and filtering the following specified amounts of compounds and as described in Example 1.

  Silicone hydrogel contact lenses obtained from this formulation exhibited a BUT of water of less than 5 seconds.

Example 18
Polymerizable silicone hydrogel contact lens precursor compositions were obtained by mixing and filtering the following specified amounts of compounds and as described in Example 1.

Example 19
Polymerizable silicone hydrogel contact lens precursor compositions were obtained by mixing and filtering the following specified amounts of compounds and as described in Example 1.

Example 20
Polymerizable silicone hydrogel contact lens precursor compositions were obtained by mixing and filtering the following specified amounts of compounds and as described in Example 1.

Example 21
Polymerizable silicone hydrogel contact lens precursor compositions were obtained by mixing and filtering the following specified amounts of compounds and as described in Example 1.

Example 22
Polymerizable silicone hydrogel contact lens precursor compositions were obtained by mixing and filtering the following specified amounts of compounds and as described in Example 1.

Example 23
Polymerizable silicone hydrogel contact lens precursor compositions were obtained by mixing and filtering the following specified amounts of compounds and as described in Example 1.

  Silicone hydrogel contact lenses obtained from this formulation had eye-acceptable surface wettability. These contact lenses have an equilibrium water content of about 63%, a BUT of water longer than 19 seconds, a static contact angle of about 39 °, an advancing contact angle of about 93 °, a receding contact angle of about 46 °, and a Young of about 0.4 MPa. It had a modulus and an elongation of about 109%.

Example 24
Polymerizable silicone hydrogel contact lens precursor compositions were obtained by mixing and filtering the following specified amounts of compounds and as described in Example 1.

  Silicone hydrogel contact lenses obtained from this formulation had eye-acceptable surface wettability.

Example 25
Polymerizable silicone hydrogel contact lens precursor compositions were obtained by mixing and filtering the following specified amounts of compounds and as described in Example 1.

  Silicone hydrogel contact lenses obtained from this formulation had eye-acceptable surface wettability.

Example 26
Polymerizable silicone hydrogel contact lens precursor compositions were obtained by mixing and filtering the following specified amounts of compounds and as described in Example 1.

  Silicone hydrogel contact lenses obtained from this formulation had eye-acceptable surface wettability.

Example 27
Polymerizable silicone hydrogel contact lens precursor compositions were obtained by mixing and filtering the following specified amounts of compounds and as described in Example 1.

  Silicone hydrogel contact lenses obtained from this formulation had eye-acceptable surface wettability. These contact lenses have an equilibrium water content of about 63%, a BUT of water longer than 25 seconds, an ion flux of about 17, a static contact angle of about 43 °, an advancing contact angle of about 94 °, and a receding contact angle of about 48 °. A Young's modulus of about 0.3 MPa, an elongation of about 166%, and a tensile strength of about 0.3.

Example 28
Polymerizable silicone hydrogel contact lens precursor compositions were obtained by mixing and filtering the following specified amounts of compounds and as described in Example 1.

  Silicone hydrogel contact lenses obtained from this formulation had eye-acceptable surface wettability.

Example 29
Polymerizable silicone hydrogel contact lens precursor compositions were obtained by mixing and filtering the following specified amounts of compounds and as described in Example 1.

  Silicone hydrogel contact lenses (cured by UV irradiation) obtained from this formulation had eye-acceptable surface wettability.

Example 30
Polymerizable silicone hydrogel contact lens precursor compositions were obtained by mixing and filtering the following specified amounts of compounds and as described in Example 1.

  Silicone hydrogel contact lenses obtained from this formulation had eye-acceptable surface wettability.

Example 31
Polymerizable silicone hydrogel contact lens precursor compositions were obtained by mixing and filtering the following specified amounts of compounds and as described in Example 1.

  Silicone hydrogel contact lenses obtained from this formulation had eye-acceptable surface wettability. These contact lenses have an equilibrium water content of about 54%, a BUT of water longer than 17 seconds, a static contact angle of about 36 °, an advancing contact angle of about 87 °, a receding contact angle of about 44 °, and an ion flux of about 8. A Young's modulus of about 0.5 MPa, an elongation of about 335%, and a tensile strength of about 0.4.

Example 32
Polymerizable silicone hydrogel contact lens precursor compositions were obtained by mixing and filtering the following specified amounts of compounds and as described in Example 1.

  Silicone hydrogel contact lenses obtained from this formulation had eye-acceptable surface wettability. These contact lenses have an equilibrium water content of about 66%, a BUT of water longer than 17 seconds, a static contact angle of about 33 °, an advancing contact angle of about 81 °, a receding contact angle of about 45 °, and a Young of about 0.4 MPa. It had a modulus, an elongation of about 131%, and a tensile strength of about 0.3.

Example 33
Polymerizable silicone hydrogel contact lens precursor compositions were obtained by mixing and filtering the following specified amounts of compounds and as described in Example 1.

  Silicone hydrogel contact lenses obtained from this formulation had eye-acceptable surface wettability. These contact lenses have an equilibrium water content of about 63%, a BUT of water longer than 19 seconds, an ionoflux of about 18, a static contact angle of about 37 °, an advancing contact angle of about 101 °, and a receding contact angle of about 46 °. A Young's modulus of about 0.4 MPa, an elongation of about 155%, and a tensile strength of about 0.4.

Example 34
Polymerizable silicone hydrogel contact lens precursor compositions were obtained by mixing and filtering the following specified amounts of compounds and as described in Example 1.

  Silicone hydrogel contact lenses obtained from this formulation had eye-acceptable surface wettability. The amount of extractable present in the polymerized lens product is estimated to be greater than 10% and about 40-42%.

Example 35
Polymerizable silicone hydrogel contact lens precursor compositions were obtained by mixing and filtering the following specified amounts of compounds and as described in Example 1.

  Silicone hydrogel contact lenses obtained from this formulation had eye-acceptable surface wettability. The amount of extractable present in the polymerized lens product is estimated to be greater than 10% and about 40-42%.

Example 36
Polymerizable silicone hydrogel contact lens precursor compositions were obtained by mixing and filtering the following specified amounts of compounds and as described in Example 1.

  Silicone hydrogel contact lenses obtained from this formulation had eye-acceptable surface wettability. These silicone hydrogel contact lenses had an equilibrium water content of 61.3 ± 0.05% and an extractable content of 17.5 ± 0.5%.

Example 37
Polymerizable silicone hydrogel contact lens precursor compositions were obtained by mixing and filtering the following specified amounts of compounds and as described in Example 1.

  Silicone hydrogel contact lenses obtained from this formulation had eye-acceptable surface wettability. These silicone hydrogel contact lenses had an equilibrium water content of 61.3 ± 0.05% and an extractable content of 17.5 ± 0.5%.

Example 38
Polymerizable silicone hydrogel contact lens precursor compositions were obtained by mixing and filtering the following specified amounts of compounds and as described in Example 1.

  Silicone hydrogel contact lenses obtained from this formulation had eye-acceptable surface wettability. These silicone hydrogel contact lenses had an equilibrium water content of 54.6 ± 1.27% and an extractable content of 23.6 ± 0.1%.

Example 39
Polymerizable silicone hydrogel contact lens precursor compositions were obtained by mixing and filtering the following specified amounts of compounds and as described in Example 1.

  Silicone hydrogel contact lenses obtained from this formulation had eye-acceptable surface wettability. These contact lenses have about 55% equilibrium water content, about 7 ion flux, about 34 ° static contact angle, about 65 ° advancing contact angle, about 50 ° receding contact angle, about 0.6 MPa Young modulus, It had an elongation of about 238% and a Dk of about 109. These hydrogel contact lenses had an extractable amount of 23.6 ± 0.1%.

Example 40
Polymerizable silicone hydrogel contact lens precursor compositions were obtained by mixing and filtering the following specified amounts of compounds and as described in Example 1.

  Silicone hydrogel contact lenses obtained from this formulation had eye-acceptable surface wettability. These silicone hydrogel contact lenses had an equilibrium water content of 47.6 ± 0.5% and an extractable content of 48.9 ± 0.7%.

Example 41
Polymerizable silicone hydrogel contact lens precursor compositions were obtained by mixing and filtering the following specified amounts of compounds and as described in Example 1.

  Silicone hydrogel contact lenses obtained from this formulation had eye-acceptable surface wettability. These contact lenses have an equilibrium water content of about 55%, an ion flux of about 6, a static contact angle of about 35 °, an advancing contact angle of about 73 °, a receding contact angle of about 49 °, a Young modulus of about 0.3 MPa, It had an elongation of about 265% and a Dk of about 98.

Example 42
Polymerizable silicone hydrogel contact lens precursor compositions were obtained by mixing and filtering the following specified amounts of compounds and as described in Example 1.

  Silicone hydrogel contact lenses obtained from this formulation had eye-acceptable surface wettability. These contact lenses have an equilibrium water content of about 46%, an ionoflux of about 4, a static contact angle of about 40 °, an advancing contact angle of about 78 °, a receding contact angle of about 54 °, a Young modulus of about 0.4 MPa, It had an elongation of about 219% and a Dk of about 129. These hydrogel contact lenses had an extractable amount of 50.2 ± 0.8%.

Example 43
Polymerizable silicone hydrogel contact lens precursor compositions were obtained by mixing and filtering the following specified amounts of compounds and as described in Example 1.

  Silicone hydrogel contact lenses obtained from this formulation had eye-acceptable surface wettability.

Example 44
Polymerizable silicone hydrogel contact lens precursor compositions were obtained by mixing and filtering the following specified amounts of compounds and as described in Example 1.

  Silicone hydrogel contact lenses obtained from this formulation had eye-acceptable surface wettability.

Example 45
Polymerizable silicone hydrogel contact lens precursor compositions were obtained by mixing and filtering the following specified amounts of compounds and as described in Example 1.

  Silicone hydrogel contact lenses obtained from this formulation had eye-acceptable surface wettability.

Example 46
Polymerizable silicone hydrogel contact lens precursor compositions were obtained by mixing and filtering the following specified amounts of compounds and as described in Example 1.

  Silicone hydrogel contact lenses obtained from this formulation had eye-acceptable surface wettability.

Example 47
Polymerizable silicone hydrogel contact lens precursor compositions were obtained by mixing and filtering the following specified amounts of compounds and as described in Example 1.

  Silicone hydrogel contact lenses obtained from this formulation had eye-acceptable surface wettability. These contact lenses have an equilibrium water content of about 60%, an ion flux of about 11, a static contact angle of about 46 °, an advancing contact angle of about 102 °, a receding contact angle of about 51 °, a Young modulus of about 0.2 MPa, It had an elongation of about 150% and a tensile strength of about 0.2.

Example 48
Polymerizable silicone hydrogel contact lens precursor compositions were obtained by mixing and filtering the following specified amounts of compounds and as described in Example 1.

  Silicone hydrogel contact lenses obtained from this formulation had eye-acceptable surface wettability. These contact lenses have an equilibrium water content of about 61%, an ion flux of about 14, a static contact angle of about 40 °, an advancing contact angle of about 106 °, a receding contact angle of about 52 °, a Young modulus of about 0.2 MPa, It had an elongation of about 224%, a tensile strength of about 0.3, and a Dk of about 69.

Example 49
Polymerizable silicone hydrogel contact lens precursor compositions were obtained by mixing and filtering the following specified amounts of compounds and as described in Example 1.

  Silicone hydrogel contact lenses obtained from this formulation had eye-acceptable surface wettability.

Example 50
Polymerizable silicone hydrogel contact lens precursor compositions were obtained by mixing and filtering the following specified amounts of compounds and as described in Example 1.

Example 51
Polymerizable silicone hydrogel contact lens precursor compositions were obtained by mixing and filtering the following specified amounts of compounds and as described in Example 1.

Example 52
Polymerizable silicone hydrogel contact lens precursor compositions were obtained by mixing and filtering the following specified amounts of compounds and as described in Example 1.

Example 53
Polymerizable silicone hydrogel contact lens precursor compositions were obtained by mixing and filtering the following specified amounts of compounds and as described in Example 1.

Example 54
Polymerizable silicone hydrogel contact lens precursor compositions were obtained by mixing and filtering the following specified amounts of compounds and as described in Example 1.

Example 55
Polymerizable silicone hydrogel contact lens precursor compositions were obtained by mixing and filtering the following specified amounts of compounds and as described in Example 1.

Example 56
Polymerizable silicone hydrogel contact lens precursor compositions were obtained by mixing and filtering the following specified amounts of compounds and as described in Example 1.

Example 57
Polymerizable silicone hydrogel contact lens precursor compositions were obtained by mixing and filtering the following specified amounts of compounds and as described in Example 1.

Example 58
Silicone hydrogel contacts were prepared from a non-polar resin lens mold from the lens precursor composition obtained as described in Example 1 by mixing and filtering the following specified amounts of the compound.

The R1 lens had an equilibrium water content of 63.1% and showed a water BUT of 4.7 seconds after 24 hours and 9 seconds after 4 days. The R1 lens product had an extractable content of about 16%.
The R3 lens had an equilibrium water content of 56% and showed a water BUT of 18 seconds after 24 hours and 20 seconds after 4 days. The R3 lens product had an extractable content of about 26%. R3 lens has 34.1 ° contact angle, 106.3 ° advancing contact angle, 52.4 ° receding contact angle, 53.9 ° hysteresis, 5.5 × 10 ⁻³ mm ² / min ionoflux, 0.42 MPa modulus, 135% elongation And tensile strength of 0.27 MPa.
The R7 lens had an equilibrium water content of 60.8% and showed a water BUT of 20 seconds after 24 hours and 20 seconds after 4 days. The R7 lens product had an extractable content of about 25%. R7 lens has 33.7 ° contact angle, 103.7 ° advancing contact angle, 53.9 ° receding contact angle, 49.8 ° hysteresis, 8.1 × 10 ⁻³ mm ² / min ionoflux, 0.33 MPa modulus, 139% elongation And tensile strength of 0.24 MPa.
The R8 lens had an equilibrium water content of 64.2% and showed a water BUT of 4.3 seconds after 24 hours and 9 seconds after 4 days. The R8 lens product had an extractable content of about 15%.
The R9 lens had an equilibrium water content of 63.9% and showed a water BUT of 1.3 seconds after 24 hours and 7 seconds after 4 days. The R9 lens product had an extractable content of about 13%.
The R0 lens had an equilibrium water content of 63.8% and showed a water BUT of 15 seconds after 24 hours and 20 seconds after 4 days. The R0 lens product had an extractable content of about 22%. R0 lens has 38 ° contact angle, 101.3 ° advancing contact angle, 48.7 ° receding contact angle, 52.6 ° hysteresis, 11.7 × 10 ⁻³ mm ² / min ionoflux, 0.42 MPa modulus, 191% elongation And tensile strength of 0.35 MPa.

Example 59
The effects of various cross-linking agents on the extractable component content were also evaluated. Silicone hydrogel contact lenses were produced in a non-polar resin lens mold without surface treatment or polymer IPN.
The components of the lens preparation are shown in the table below. The extractable component content was measured by changing the type and concentration of the crosslinking agent.

MIX#3：1:1比のTEGDMAとTEGDVE

MIX # 3: 1: 1 ratio of TEGDMA and TEGDVE

These results were derived from silicone hydrogel contact lens products with high extractable component content (e.g., greater than 16.9%), which contained VMA and IBM derived units and utilized dimethacrylate or trimethacrylate based crosslinkers. It shows that a silicone hydrogel contact lens was obtained. In contrast, lens products containing units derived from VMA and IBM and utilizing vinyl methacrylate or triallyl isocyanurate crosslinkers had lower extractable component content (eg, less than 10%). The lens product using triethylene glycol divinyl ether as the crosslinker had an extractable component content of 10.3%.
In this study, 80% of the contact lenses obtained with each of the formulation names T31A; T31C; T31C1; T31C2; T31E; T31F; and T31G showed water BUTs over 20 seconds. 60% of the T31 lenses showed a 10 second water BUT and only 40% of the T31B lens showed a 5 second water BUT.
Thus, in these lens formulations, dimethacrylate and trimethacrylate based crosslinkers can consistently provide silicone hydrogel contact lens products with high extractable components. Silicone hydrogel contact lenses obtained from this lens product have desirable surface wettability.
These data show that when these silicone hydrogel lens products have an extractable component content higher than 10%, or the silicone hydrogel contact lenses obtained therefrom do not exceed 90% of the dry weight of the respective lens product. It also supports that when having weight, the silicone hydrogel contact lens can have eye-acceptable surface wettability.

Example 60
The silicone hydrogel contact lens examples were compared to existing silicone hydrogel contact lenses as shown in the table below. Lens A is an Acuvue Advance contact lens (Johnson &Johnson); Lens B is an Acuvue Oasys contact lens (Johnson &Johnson); Lens C is an O ₂ Optix contact lens (Ciba Vision); and Lens D is a Biofinity contact lens (CooperVision) is there.

EWC：平衡含水量(%)
ACA：前進接触角(度)
RCA：後退接触角(度)
PSHCLP：重合したシリコーンヒドロゲルコンタクトレンズ生成物
SHCL：シリコーンヒドロゲルコンタクトレンズ(抽出及び水和後)

EWC: Equilibrium water content (%)
ACA: Advance contact angle (degrees)
RCA: receding contact angle (degrees)
PSHCLP: Polymerized silicone hydrogel contact lens product
SHCL: Silicone hydrogel contact lens (after extraction and hydration)

Example 61
The silicone hydrogel contact lens examples were compared to silicone hydrogel contact lenses obtained from non-polar resin contact lens molds using the Biofinity silicone hydrogel contact lens lens precursor composition. The lens precursor composition used in the manufacture of Biofinity silicone hydrogel contact lenses has an extractable amount of less than 10% (w / w), e.g. about 8% (w / w), before being polymerized silicone hydrogel contact A lens product is produced. When the precursor composition is cured, extracted and hydrated in a non-polar resin lens mold, the resulting silicone hydrogel contact lens has a dry weight of about 92% of the lens product prior to extraction. It has a lens body. The hydrated contact lenses so produced had surface wettability that was unacceptable to the eye. In contrast, the lens includes a lens body having a dry weight that does not exceed 90% of the polymerized silicone hydrogel contact lens product prior to extraction, and as described above, surface wettability acceptable to the eye. Have

While the disclosure herein refers to particular illustrated embodiments, these embodiments are presented by way of example and should not be construed as limiting. The intention of the above detailed description should be construed to include all variations, alternatives, and equivalents of the foregoing embodiments, so long as they are within the spirit and scope of the invention as defined by the further disclosure. is there.
In this specification, a number of publications and patents are cited. Each cited publication and patent is incorporated herein by reference in its entirety.

Moreover, this invention can be the following aspects.
[1]
A silicone hydrogel contact lens comprising a lens body comprising a silicone hydrogel material, wherein the lens body has acceptable surface wettability and a dry weight not exceeding 90% of the dry weight of the lens body before extraction. A silicone hydrogel contact lens.
[2]
The silicone hydrogel contact lens according to [1], wherein the lens body does not have a surface treatment that provides an acceptable surface wettability to the eye.
[3]
The silicone hydrogel contact lens according to [1] or [2], wherein the lens body does not have an interpenetrating polymer network of a polymer wetting agent that provides acceptable surface wettability to the eye.
[4]
The silicone hydrogel contact lens according to any one of [1] to [3], wherein the lens body is a cast molding element obtained from a non-polar resin contact lens mold.
[5]
The lens body is hydrated and has an advancing contact angle of less than about 120 degrees, a tensile modulus of less than about 1.6 MPa, an ion flux of less than about 7 10 ^-3 mm ² / min, and an oxygen permeability of at least about 70 barrer . And a silicone hydrogel contact lens according to any one of [1] to [4], comprising one or more features selected from a water content of at least about 30% by weight.
[6]
A silicone hydrogel contact lens comprising a lens body obtained from a pre-extracted polymerized silicone hydrogel contact lens product having a removable component content of at least 10% (w / w), said lens body comprising Silicone hydrogel contact lenses having ocular acceptable surface wettability.
[7]
The silicone hydrogel contact lens according to [6], wherein the lens body is a non-surface-treated lens body.
[8]
The silicone hydrogel contact lens according to [6] or [7], wherein the lens body does not have an interpenetrating polymer network of a polymer wetting agent that provides acceptable surface wettability to the eye.
[9]
The silicone hydrogel contact lens according to any one of [6] to [8], wherein the polymerized silicone hydrogel contact lens product is polymerized in a contact lens mold made of a nonpolar resin.
[10]
The lens body is hydrated and has an advancing contact angle of less than about 120 degrees, a tensile modulus of less than about 1.6 MPa, an ion flux of less than about 7 10 ^-3 mm ² / min, and an oxygen permeability of at least about 70 barrer . And a silicone hydrogel contact lens according to any one of [6] to [9], comprising one or more features selected from a water content of at least about 30% by weight.
[11]
The silicone hydrogel contact lens according to any one of [6] to [10], wherein the removable component of the polymerized silicone hydrogel contact lens product comprises at least one non-reactive additive.
[12]
[11] The at least one non-reactive additive is selected from one or more of a compatibilizer, a mold release aid, a de-lens aid, a wettability enhancer, and an ionoflux reducer. Silicone hydrogel contact lens.
[13]
The silicone hydrogel contact lens according to [11], wherein the at least one non-reactive additive is a hydrophobic or amphiphilic additive.
[14]
The silicone hydrogel contact lens according to [11], wherein the at least one non-reactive additive is a non-reactive alcohol, a non-reactive hydrophilic silicone polymer, or a combination thereof.
[15]
The at least one non-reactive additive is selected from one or more of ethylene glycol stearate, diethylene glycol monolaurate, C ₂ -C ₂₄ alcohol, C ₂ -C ₂₄ amine, and polydimethylsiloxane-co-PEG. The silicone hydrogel contact lens according to [11].
[16]
The silicone hydrogel contact lens according to [11], wherein the at least one non-reactive additive is decanol, polydimethylsiloxane-co-PEG, or a combination thereof.
[17]
The silicone hydrogel contact lens according to any one of [6] to [17], wherein the lens body includes a unit obtained from a methacrylate phosphorylcholine monomer.
[18]
The silicone hydrogel contact lens according to [17], wherein the lens body includes a unit obtained from 2-methacryloyloxyethyl phosphorylcholine.
[19]
A polymerized silicone hydrogel contact lens product prior to extraction, wherein the body member prior to extraction has been subjected to an extraction procedure to form an extracted polymerized silicone hydrogel contact lens product. A polymerized silicone hydrogel contact lens product prior to extraction having a dry weight at least 10% greater than the dry weight of the subsequent body member.
[20]
The polymerized silicone hydrogel contact lens production of [19], wherein the body member before extraction has a removable component content of 10% (w / w) to about 75% (w / w) of the body member object.
[21]
The polymerized silicone hydrogel contact lens product according to [19] or [20], which is provided in contact with a nonpolar resin contact lens mold member.
[22]
The polymerized silicone hydrogel contact lens product according to any one of [19] to [21], wherein the body member before extraction contains at least one non-reactive additive.
[23]
[22] The at least one non-reactive additive is selected from one or more of a compatibilizer, a mold release aid, a de-lens aid, a wettability enhancer, and an ionoflux reducer. Polymerized silicone hydrogel contact lens product.
[24]
The polymerized silicone hydrogel contact lens product according to [22], wherein the at least one non-reactive additive is a hydrophilic additive or an amphiphilic additive.
[25]
The polymerized silicone hydrogel contact lens product of [22], wherein the at least one non-reactive additive is a non-reactive alcohol, a non-reactive hydrophilic silicone polymer, or a combination thereof.
[26]
The at least one non-reactive additive is selected from one or more of ethylene glycol stearate, diethylene glycol monolaurate, C ₂ -C ₂₄ alcohol, C ₂ -C ₂₄ amine, and polydimethylsiloxane-co-PEG. The polymerized silicone hydrogel contact lens product according to [22].
[27]
The polymerized silicone hydrogel contact lens product of [22], wherein the at least one non-reactive additive is decanol, polydimethylsiloxane-co-PEG, or a combination thereof.
[28]
The polymerized silicone hydrogel contact lens product according to any one of [19] to [27], wherein the body member before extraction contains units obtained from a methacrylate phosphorylcholine-monomer.
[29]
Polymerizable silicone hydrogel contact lens precursor composition comprising a non-silicon-containing component polymerizable with a polymerizable silicon-containing component as a polymerizable silicone hydrogel contact lens precursor composition, said polymerizable silicone hydrogel contact lens A portion of the precursor composition is removable from the polymerized silicone hydrogel contact lens product made from the polymerizable silicone hydrogel contact lens precursor composition and at least 10% of the polymerized silicone hydrogel contact lens product ( A polymerizable silicone hydrogel contact lens precursor composition present in an amount of w / w).
[30]
The polymerizable non-silicon-containing component includes a first monomer having a first reactivity ratio and a second monomer having a second reactivity ratio lower than the first reactivity ratio. ] The polymerizable silicone hydrogel contact lens precursor composition according to claim 1.
[31]
The polymerizable silicone hydrogel contact lens precursor composition according to [30], wherein the polymerizable non-silicon-containing component further comprises a crosslinking agent having a reactivity ratio similar to the first reactivity ratio.
[32]
The polymerizable silicon-containing component is M3U, and the polymerizable non-silicon-containing component comprises N-vinyl-N-methylacetamide, methyl methacrylate, tri (ethylene glycol) dimethacrylate, and an initiator, 29] The polymerizable silicone hydrogel contact lens precursor composition according to [29].
[33]
The polymerizable silicone hydrogel contact lens precursor composition according to any one of [29] to [32], wherein the non-silicon-containing component further comprises an ultraviolet absorber and a colorant.
[34]
The polymerizable silicone hydrogel contact lens precursor composition according to any one of [29] to [33], further comprising a block copolymer of polydimethylsiloxane and polyethylene glycol.
[35]
The polymerizable silicon-containing component is M3U, and the polymerizable non-silicon-containing component comprises 1-vinyl-2-pyrrolidone, methyl methacrylate, tri (ethylene glycol) dimethacrylate, and an initiator. ] The polymerizable silicone hydrogel contact lens precursor composition according to claim 1.
[36]
The polymerizable silicone hydrogel contact lens precursor composition according to [35], wherein the polymerizable non-silicon-containing component further comprises decanol.
[37]
The polymerizable silicone hydrogel contact lens precursor composition according to [36], wherein the decanol is present in an amount of about 5% (w / w) to about 30% (w / w) of the composition.
[38]
The polymerizable silicone hydrogel contact lens precursor composition according to [35], further comprising a block copolymer of polydimethylsiloxane and polyethylene glycol.
[39]
The polymerizable silicone hydrogel contact lens precursor composition according to [38], further comprising a hydrophilic silicone-containing release aid or polyalkylene oxide release aid.
[40]
The polymerizable silicone hydrogel contact lens precursor composition according to [35], wherein the non-silicon-containing component further comprises a diluent selected from the group consisting of hexanol, ethoxyethanol, isopropanol, propanol, decanol, and combinations thereof. .
[41]
The polymerizable silicone hydrogel contact lens precursor composition according to [40], further comprising a unit of methacrylate phosphorylcholine-monomer.
[42]
[29] The polymerizable silicone hydrogel contact lens precursor composition according to any one of [29] to [41], further comprising an extractable hydrophobic additive or an extractable amphiphilic additive.
[43]
Said additive, ethylene glycol stearate, diethylene glycol monolaurate, C ₂ -C ₂₄ alcohols, C ₂ -C ₂₄ amines, and are selected from one or more polydimethyl siloxane -co-PEG, according to [42] A polymerizable silicone hydrogel contact lens precursor composition.
[44]
The polymerizable silicone hydrogel contact lens precursor composition according to [42], wherein the additive is decanol, polydimethylsiloxane-co-PEG, or a combination thereof.
[45]
The polymerizable silicone hydrogel contact lens precursor composition according to [44], wherein the additive comprises polydimethylsiloxane-co-PEG having a molecular weight in the range of about 300 to about 30,000 Daltons.
[46]
The polymerizable silicone hydrogel contact lens precursor composition according to [44], wherein the additive comprises polydimethylsiloxane-co-PEG having a molecular weight of less than about 3,000 daltons.
[47]
The polymerizable silicone hydrogel contact lens precursor composition according to [42], wherein the additive is present in an amount ranging from about 1% to about 60% of the composition.
[48]
The polymerizable silicone hydrogel contact lens precursor composition according to [42], comprising at least two different additives.
[49]
The polymerizable silicone hydrogel contact lens precursor composition according to [42], which is provided in a nonpolar resin contact lens mold.
[50]
A method for producing a silicone hydrogel contact lens, wherein the silicone hydrogel contact lens product prior to extraction has a removable component content of at least 10% (w / w) of the lens product prior to extraction. Forming a silicone hydrogel contact lens body having a dry weight that does not exceed 90% of the dry weight of the lens body and an ophthalmically acceptable surface wettability.
[51]
50. The method of [50], wherein the forming step comprises extracting an extractable from the silicone hydrogel contact lens product prior to extraction.
[52]
A polymerizable silicone hydrogel contact lens precursor composition is cured to have a polymerized silicone hydrogel contact lens product prior to extraction having a removable component content of at least 10% (w / w) of the lens product. The method according to [50] or [51], further comprising a step of forming what has.
[53]
The method according to [52], wherein the polymerizable silicone hydrogel contact lens precursor composition is cured in a contact lens mold of a nonpolar resin.
[54]
[52] The method according to [52], further comprising the step of adding a removable additive to the polymerizable silicone hydrogel contact lens precursor composition.
[55]
The removable additive is selected from the group consisting of compatibilizers, mold release aids, de-lens aids, wettability enhancers, modulus reducers, ionoflux reducers, and combinations thereof [54] The method described in 1.
[56]
56. The method of any one of claims 52 to 55, further comprising adding an additive selected from the group consisting of a UV absorber, a colorant, and combinations thereof to the lens precursor composition.
[57]
Any one of [50] to [56], wherein the silicone hydrogel contact lens is produced without surface-treating the lens or without forming the lens with an interpenetrating polymer network of a polymer wetting agent. The method described in 1.

Claims (18)

A method of producing a silicone hydrogel contact lens having ocular acceptable surface wettability comprising:
Providing a polymerizable silicone hydrogel contact lens precursor composition in a contact lens-shaped cavity of a non-polar resin contact lens type, wherein the polymerizable silicone hydrogel contact lens precursor composition comprises a silicon-containing component; A non-silicon-containing component, the non-silicon-containing component comprising N-vinylpyrrolidone monomer, N-vinyl-N-methylacetamide monomer, N-vinyl-N-ethylacetamide monomer, N-vinyl-N-ethylformamide monomer, N-vinylformamide monomer, N-2-hydroxyethyl vinyl carbamate monomer, N-carboxy-β-alanine N-vinyl ester monomer, or a combination thereof, and the contact lens mold includes a first contact lens mold member and Combination of second contact lens mold members Processes including
Polymerizing the polymerizable silicone hydrogel contact lens precursor composition in the non-polar resin contact lens mold to form a polymerized silicone hydrogel contact lens product prior to extraction, wherein the polymerized prior to extraction; The silicone hydrogel contact lens product has an alcohol removable component in an amount of at least 10% by weight based on the dry weight of the polymerized silicone hydrogel contact lens product prior to extraction, wherein the removable The component comprises unreacted monomer, partially reacted monomer, or both in an amount of at least 10% by weight based on the dry weight of the polymerized silicone hydrogel contact lens product prior to extraction;
The pre-extracted polymerized silicone hydrogel contact lens product is extracted and hydrated by contacting the pre-extracted polymerized silicone hydrogel contact lens product with an extraction medium containing alcohol to obtain a pre-extraction polymerized hydrogel contact lens product. Manufacturing a silicone hydrogel contact lens having a dry weight of 90% or less of the dry weight of the polymerized silicone hydrogel contact lens product; and packaging the silicone hydrogel contact lens in a contact lens package;
Including methods.   The method of claim 1, wherein the removable component is present in an amount of at least 15 wt% based on the dry weight of the polymerized silicone hydrogel contact lens product prior to extraction.   The method of claim 1, wherein the non-silicon containing component of the precursor composition comprises an N-vinyl pyrrolidone monomer.   The method of claim 1, wherein the non-silicon containing component of the precursor composition comprises N-vinyl-N-methylacetamide monomer.   The non-silicon-containing component of the precursor composition is N, N-dimethylacrylamide monomer, 2-hydroxyethyl acrylate monomer, glycerol methacrylate monomer, 2-hydroxyethyl methacrylamide monomer, polyethylene glycol monomethacrylate monomer, or polyethylene glycol dimethacrylate The method of claim 1, further comprising a monomer, or a combination thereof.   The method of claim 1, wherein the non-silicon-containing component comprises a hydrophilic component in an amount of 10% to 60% by weight relative to the weight of all reactive components of the precursor composition.   The method of claim 1, wherein the extraction occurs at a temperature of 20 ° C. to 100 ° C.   The method of claim 1, wherein the extraction medium comprises ethanol, methanol or propanol.   The method of claim 1, wherein the extraction medium comprises water.   The method of claim 1, wherein the precursor composition further comprises a removable additive that does not covalently bind to the polymerized silicone hydrogel contact lens product prior to extraction.   11. The method of claim 10, wherein the additive is a diluent in an amount of 1% to 60% by weight of the precursor composition.   The method of claim 1, wherein the silicone hydrogel contact lens comprises the removable component in an amount of 0.1 wt% to 4 wt%.   The method of claim 1, wherein the silicone hydrogel contact lens has an oxygen permeability not less than 60 barrer.   The method of claim 1, wherein the silicone hydrogel contact lens has an equilibrium water content of at least 30% by weight.   The method of claim 14, wherein the silicone hydrogel contact lens has an equilibrium water content of 35% to 65% by weight. The silicone hydrogel contact lens has an advancing contact angle of less than 120 degrees, a tensile modulus of less than 1.6 MPa, an ionoflux of less than 7 × 10 ⁻³ mm ² / min, an oxygen permeability of at least 70 barrer, or at least 30% by weight. The method of claim 1, having an equilibrium water content, or a combination thereof.   2. The precursor composition of claim 1, wherein the precursor composition comprises a first monomer having a first reactivity ratio and a second monomer having a second reactivity ratio that is lower than the first reactivity ratio. Method.   The method of claim 1, wherein the precursor composition comprises a methacrylate phosphorylcholine monomer.

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