Hydrogel intraocular lens and method of its formation

FIELD: medicine.

SUBSTANCE: claimed invention is aimed at manufacturing intraocular lens (IOL), for introduction of posterior eye chamber in form of PC Phakic lens. IOL is formed from hydrogel material, formed by cross-linked polymer and copolymer component. Lens includes UV chromophore, which is benzotriazole.

EFFECT: IOL hydrogel material usually has relatively high index of refraction and/or possesses desirable degree of protection against irradiation.

12 cl, 3 tbl

 

Cross-reference to related application

The present application claims priority from provisional patent application U.S. serial No. 61/039896, filed on March 27, 2008

The technical field of the invention

The present invention relates to ophthalmic materials devices and, more particularly, to intraocular lens (IOL), formed from acrylate hydrogel material having a desired refractive index, the desired degree of protection from radiation, the desired ion permeability, or a combination thereof.

Background of the invention

The present invention is directed to ophthalmic devices and, in particular, intraocular lens (IOL). IOLs have been developed and introduced in different parts of the eye and can be used to compensate or correct the vision, provide the natural lens of the eye, or can replace the natural lens of the eye. Lenses that compensate for or correct vision without replacement of the natural lens, usually called Phakic lenses, while lenses that replace the natural crystalline lens, usually called Aphakic lenses. The Phakic lenses can be positioned in the anterior chamber (AC) of the eye (lens AC Phakic) or posterior chamber (PC) of the eye (lens PC Phakic).

IOL can be made of several materials. Recently, one of the ako, there was a trend towards the use of soft, foldable material, which are easier to enter into the eye through a small incision in the eye. In General, materials such lenses are divided into the following categories: hydrogels; silicones and dehydrogenase acrylic materials.

Usually it is desirable that the material of the IOL had a relatively high refractive index, so that the IOL can be relatively thin and still show a relatively high degree of vision correction. In particular, this is true in the case of PC lenses Phakic. Historically, however, hydrogel materials usually showed undesirable low indices of refraction. Therefore, researchers have spent the time and effort to search hydrogel materials having higher refractive indices. Examples of such materials are discussed in U.S. patents№№: 4036814; 4123407; 4123408; 4430458; 4495313; 4680336; 4620954; 4749761; 4866148; 4889664; 5135965; 5824719; 5936052; 6015842 and 6140438, and in patent publication U.S. 2002/0128417, all of which are fully incorporated here by reference for all purposes.

Although these new materials have provided the desired refractive indices, they also have disadvantages. In particular, it was found that these materials can have unwanted degrees of degradation when exposed to electromagnetic radiation, especially ultraviolet (UV) radiation. This degradative to suppress or impair the ability of the IOL to correct the vision of the individual and could potentially cause other problems with vision, such as blurred vision or spots.

There are many known compounds (for example, UV chromophores), which was introduced in the composition of the ophthalmic lens (e.g., IOLs and contact lenses to protect the eye tissues from harmful electromagnetic radiation. Such compounds can absorb the dangerous UV radiation, so it does not reach the eye tissue. At the same time, however, these compounds usually do not protect yourself ophthalmic lenses from dangerous radiation and can in many cases to accelerate the degradation of ophthalmic lenses, because the dangerous rays are absorbed within the lens. This type of degradation can be particularly harmful for IOL, because such lenses are commonly implanted in the eye for long periods of time, and during these periods of time the radiation may be undesirable to change the characteristics (for example, refractive index, optical power, the ability to deletion or the like) of the lens.

Hydrogel lenses can be quite sensitive to degradation from UV and other radiation. In addition, this degradation can be increased with the inclusion of some lenses UV chromophores. There is very little protective compounds that are suitable for use in hydrogel IOL (especially PC IOL Phakic), where these compounds do not enhance the degradation or the state Duma of the connection to protect the IOL material from dangerous electromagnetic radiation.

In addition, hydrogel lenses are often required relatively high concentrations of UV chromophores to provide the desired degree of UV absorption. However, such concentrations can reduce ion permeability or other desired properties of the lens.

Thus, there is a need in the hydrogel IOL, which includes effective, resistant to UV connection including a material such IOL has the desired degree of resistance to degradation, which could otherwise be caused by exposure to electromagnetic radiation. In addition, it would be particularly desirable that the material of the IOL had a relatively high refractive index and relatively high ion permeability and/or a relatively low refractive index and/or optical power due to the effects of radiation.

The invention

The present invention is directed to hydrogel material, suitable for use as an intraocular lens, and IOL formed in this material. Intraocular lens can be made with the possibility of introducing into the rear chamber or anterior chamber of the eye and can be made in the form of lenses Phakic or Aphakic. Preferably, however, the lens is made according to the size and shape of the lens PC Phakic. The lens and/or hydrogel lens material is usually formed of cross-school is th acrylate polymer. The lens and/or hydrogel material also typically includes a UV chromophore, and this UV chromophore usually includes benzotriazole (for example, 2-(2-hydroxyphenyl)benzotriazol). Preferably, the UV chromophore greatly enhances the stability of the lens to degradation under the action of electromagnetic radiation.

UV chromophores suitable for use in the materials of the ophthalmic devices of the present invention, represented by formula (A).

,

for formula (A)

R1represents a substituted or unsubstituted With1-C6alkyl, halogen, OH, C1-C12alkoxy, optionally substituted, phenoxy or optionally substituted, naphthyloxy, where the optional substituents are C1-C6alkyl, C1-C6alkoxy, OH, -(CH2CH2O)n- or -(CH2CH(CH3)O)n-;

R2represents a C1-C12alkyl, (CH2CH2O)n, (CH2CH(CH3)O)nor CH2CH2CH2(Si(CH3)2O)mSi(CH3)2CH2CH2CH2;

X is absent if R2represents (CH2CH2O)nor (CH2CH(CH3)O)notherwise X represents O, NR4or S;

R3absent or represents C(=O)C(=O)CjH 2jC1-C6alkyl, phenyl or C1-C6alkylphenyl;

R4represents H or methyl;

R5represents H, C1-C6alkyl or phenyl;

R6represents H, C1-C12alkyl or C1-C12alkyloxy (e.g., methoxy);

R7represents a C1-C6alkyl or is absent;

m is 1-9;

n is 2-10; and

j is 1-6.

In preferred variants of the invention, the polymeric material includes a first monomer comprising one or more nitrogen-containing monomers, preferably circular, and most preferably heterocyclic nitrogen-containing monomers. It is assumed that the polymeric material of the hydrogel may include vanillacream, and most preferably may include a copolymer of NVP and methacrylate. In a very preferred embodiment of the invention vanillacream includes NVP-co-hydroxynitrile, NVP-co-allmaterial or a combination thereof.

Detailed description of the invention

The present invention is intended to provide an intraocular lens (IOL), which is formed from a hydrogel material and which includes resistant to radiation ingredient or compound (i.e. ultraviolet (UV) chromophore). Resistant to UV connection b the children usually help hydrogel material to resist degradation, which he would otherwise experience due to exposure to electromagnetic radiation, especially UV radiation.

As used herein, the term "hydrogel" or "hydrogel material" means material that contains more than 30% by weight of water, when such material is located in the aquatic environment in the human eye.

As used herein, the term "electromagnetic radiation" includes all the light in the electromagnetic spectrum, whether visible or invisible.

The hydrogel material used for the formation of the IOL of the present invention will typically include a polymeric material. The polymeric material may consist of a single polymer or a number or mixture of polymers. The polymeric material may include a thermoplastic polymer and will normally include a thermosetting or termotehnica polymer. The polymeric material may include polymers with a single repeating element, copolymers, or both.

Preferably, the polymeric material of the hydrogel comprises a copolymer component or formed partially, completely or almost completely from the copolymer component, which consists of a copolymer with a mixture of the first monomer and the second monomer.

In preferred variants of the invention, the first monomer can be represented by a nitrogen-containing monomers, site is preferably circular and most preferably heterocyclic nitrogen-containing monomers. Especially preferred are heterocyclic N-vinyl monomers, for example, N-vinylacetate. Preferred N-vinylacetate are pyrrolidone, piperidone and caprolactam and derivatives thereof, such as N-vinyl-2-piperidone, N-vinyl-2-pyrrolidone, N-vinylcaprolactam or their derivatives. It is assumed that at least 80%, 90% or more by weight of the first monomer may consist of any one of these monomers or from any combination thereof.

As a Supplement or alternative to N-vinylacetal, can be used heterocyclic N-vinyl monomers, such as N-vinylimidazole, N-vinylamine or N-vinylphthalimide.

Alternative or additional nitrogen-containing heterocyclic monomers to the monomers mentioned above are aminopropane (meth)acrylic compounds, for example, (meth)acrylamide or N-substituted derivative. Preferred are those which are mono - or disubstituted, for example, alkilany, hydroxyalkylated or aminoalkylated substituents. Specific examples of such materials are N-methylacrylamide, N-izopropilakrilamid, N-diacetonitrile, N,N-dimethylacrylamide, N,N-dimethylaminoethylacrylate, N,N-dimethylaminoethylacrylate, N-methylaminopropane or methacrylamides similar to any of the above.

The second monomer, copolym REGO material typically has the formula 1, below:

,

where X represents N or CH3;

m is 0-10;

Y is absent or represents O, S or NR, where R represents H, CH3CnH2n+1(n=1-10), ISO-OC3H7C6H5or CH2With6H5;

Ar is any aromatic ring which can be unsubstituted or substituted CH3With2H5the h3H7ISO-C3H7The co3With6H11With6H5or CH2With6H5;

Suitable monomers of structure (I) include, but are not limited to: 2-ethylenemethacrylic; 2-ethylenemethacrylic; 2-ethylthiomethyl; 2-ethyldiethanolamine; 2-ethylenevinylacetate; 2-ethylenevinylacetate; fenilsalicilat; phenylacrylate; bezelmaterial; benzoylacrylate; 2-fenilatilmalonamid; 2-phenylethylamine; 3-phenylpropionitrile; 3-phenylpropylamine; 4-fenilmetilketil; 4-phenylbutyramide; 4-methylphenylethyl; 4-methylphenylacetic; 4-methylbenzonitrile; 4-methylbenzylamine; 2-2-methylphenylacetonitrile; 2-2-methylphenylethylamine; 2-3-methylphenylacetonitrile; 2-3-methylphenylethylamine; 2-4-methylphenylacetonitrile; 2-4-methylphenylethylamine; 2-(4-propylphenyl)ethyl methacrylate; 2-(4-propylphenyl)acrylate; 2-(4-(1-mutilat the l)phenyl)ethyl methacrylate; 2-(4-(1-methylethyl)phenyl)acrylate; 2-(4-methoxyphenyl)ethyl methacrylate; 2-(4-methoxyphenyl)acrylate; 2-(4-cyclohexylphenol)ethyl methacrylate; 2-(4-cyclohexylphenol)acrylate; 2-(2-chlorophenyl)ethyl methacrylate; 2-(2-chlorophenyl)acrylate; 2-(3-chlorophenyl)ethyl methacrylate; 2-(3-chlorophenyl)acrylate; 2-(4-chlorophenyl)ethyl methacrylate; 2-(4-chlorophenyl)acrylate; 2-(4-bromophenyl)ethyl methacrylate; 2-(4-bromophenyl)acrylate; 2-(3-phenylphenyl)ethyl methacrylate; 2-(3-phenylphenyl)acrylate; 2-(4-phenylphenyl)ethyl methacrylate; 2-(4-phenylphenyl)acrylate; 2-(4-benzoylphenyl)ethyl methacrylate; and 2-(4-benzoylphenyl)acrylate, and the like.

The preferred monomers of structure (I) are those in which m is 2-4, Y is absent or represents O, and Ar is phenyl. Most preferred are 2-phenylethylamine, 2-fenilatilmalonamid and combinations thereof. It is assumed that at least 80%, 90% or more by weight of the second monomer comprises one or both of these two monomers.

It should be understood that the copolymer component formed from the first monomer and the second monomer may include a number of different copolymers with any of the monomers mentioned in the group of monomers suitable as a first monomer, and any of the monomers mentioned in the group of monomers that are suitable as the second monomer. Copolymer component t is the train can be formed from a single copolymer. Preferred copolymers suitable for the copolymer component include, without limitation, N-vinyl-2-pyrrolidone - co-helmetcrest, N-vinyl-2-pyrrolidone - co-hydroxy(alkyl)methacrylate, or combinations thereof.

Copolymer component is typically at least 30%, more typically at least 60%, and even more typically at least 80% or even at least 90% by weight of addition polymer material or a hydrogel material, which forms IOL. Copolymer component is also typically less than approximately 99.5% by weight in hydrogel material, which forms IOL. Unless otherwise stated, percentages (e.g., mass percent) for ingredients hydrogel material are given as anhydrous interest or interest that does not include water or other aqueous medium, which will usually be impregnated with a hydrogel when exposed to a water environment. Such hydrogel material is usually completely solid with regard to such mass percent before the impact of the aquatic environment.

To initiate polymerization of the monomers and/or implementation of cross-stitching or heat polymers (e.g., copolymers), formed from these monomers typically use a hardener (e.g., the initiator). Examples of suitable curing agents include peroxide hardeners (i.e. l is the battle hardener, comprising a peroxide group), an oxide hardeners (i.e. any compound including an oxide group (for example, dioxide)or other well-known experts in this field. One example of the preferred peroxide curing agent is an organic peroxide initiator tert-butyl peroxy-2-ethylhexanoate. Such a curing agent is particularly suitable for heat curing. One example of oxide curing agent is an oxide, 2,4,6-trimethylbenzenesulfonyl. Such a curing agent is particularly suitable for curing blue light.

Can also be used in the curing accelerators. Various curing accelerators are known and can be used in prescribed amounts or quantities experimentally found suitable. Usually, the amount of curing agent, curing accelerator, or combinations thereof comprise between about 0.1% and about 8% by weight of hydrogel material.

The curing agents and curing accelerators can be used in different amounts, which will usually depend on the used monomers and polymers, any used for curing and environmental conditions (e.g. heat, light or otherwise) and/or other factors.

As discussed above, the hydrogel material of the present invention includes sustainably is to beam connection. Resistant to radiation of the connection can be a single compound or may be a mixture of many compounds.

As used here, "resistant to radiation connection" is a connection that would help such a hydrogel material, especially a polymer component of the hydrogel material to resist degradation (for example, changes in the shape, size, color, refractive index, ionic permeability, equilibrium water contents (RVS) or the like), which would otherwise be caused by exposure to electromagnetic radiation. Resistant to radiation connection can resist degradation, which could otherwise be caused by electromagnetic radiation in any part of the electromagnetic spectrum. However, it is in General preferred to resistant to radiation connection resisted degradation, which could otherwise be caused by exposure to UV radiation (i.e. electromagnetic radiation with a wavelength in the range of 100 nm or 150 nm to 400 nm), which may include middle UV (i.e. wavelengths in the range from 300 nm to 400 nm), the average UV (i.e. wavelengths in the range from 200 nm to 300 nm), vacuum ultraviolet (i.e. wavelengths in the range from 150 nm to 200 nm), or any combination.

Mostly, it was found that separate UV chromium is ora provide UV protection hydrogel materials of the present invention or, at least not significantly increase the degradation of IOL materials exposed to UV. In particular, it was shown that benzotriazole of the present invention to provide such characteristics.

Preferred benzotriazole include, without limitation, substituted 2-hydroxyphenyltriazine UV absorbers. UV chromophores suitable for use in the materials of the ophthalmic devices of the present invention, represented by formula (A)

,

for formula (A)

R1represents a substituted or unsubstituted C1-C6alkyl, halogen, OH, C1-C12alkyloxy, optionally substituted, phenoxy or optionally substituted, naphthyloxy, where the optional substituents are C1-C6alkyl, C1-C6alkoxy, OH, -(CH2CH2O)n- or -(CH2CH(CH3)O)n-;

R2represents a C1-C12alkyl, (CH2CH2O)n, (CH2CH(CH3)O)nor CH2CH2CH2(Si(CH3)2O)mSi(CH3)2CH2CH2CH2;

X is absent if R2represents (CH2CH2O)nor (CH2CH(CH3)O)notherwise X represents O, NR4or S;

R3missing or before the hat is C(=O), C(=O)CjH2jC1-C6alkyl, phenyl or C1-C6alkylphenyl;

R4represents H or methyl;

R5represents H, C1-C6alkyl or phenyl;

R6represents H, C1-C12alkyl or C1-C12alkyloxy (e.g., methoxy);

R7represents a C1-C6alkyl or is absent;

m is 1-9;

n is 2-10; and

j is 1-6.

Particularly preferred UV chromophores, which also have the formula (A), suitable for use in the materials of the ophthalmic devices of the present invention, represented by formula (I)

,

for formula (I)

R1represents halogen, OH, C1-C12alkyloxy, optionally substituted, phenoxy or optionally substituted, naphthyloxy, where the optional substituents are C1-C6alkyl, C1-C6alkoxy, OH, -(CH2CH2O)n- or -(CH2CH(CH3)O)n-;

R2represents a C1-C12alkyl, (CH2CH2O)n, (CH2CH(CH3)O)nor CH2CH2CH2(Si(CH3)2O)mSi(CH3)2CH2CH2CH2;

X is absent if R2represents (CH2CH2O)n 2CH(CH3)O)notherwise X represents O, NR4or S;

R3absent or represents C(=O)C(=O)CjH2jC1-C6alkyl, phenyl or C1-C6alkylphenyl;

R4represents H or methyl;

R5represents H, C1-C6alkyl or phenyl;

R6represents H or C1-C12alkyl;

m is 1-9;

n is 2-10; and

j is 1-6.

Preferably, in the formula (I) and/or (A)

R1represents Cl, Br, C1-C4alkoxy or phenoxy;

R2represents a C1-C6alkyl;

X represents O or NR4;

R3represents C(=O) or C1-C6alkylphenyl;

R4represents H or methyl;

R5represents H; and

R6represents a C4-C12t-alkyl.

Most preferably, in the formula (I) or (A)

R1represents methoxy;

R2represents a C2-C3alkyl;

X represents O;

R3represents C(=O);

R4represents H or methyl;

R5represents H; and

R6represents t-butyl.

The compounds of formula (a) and (I) can be obtained using methods known in this field the tee. Two preferred compounds of formulas (a) and (I) are 2-{2'-hydroxy-3'-tert-butyl-5'-[3"-(4"'-vinylbenzoate)propoxy]phenyl}-5-methoxy-2H-benzotriazol:

and 2-[2'-hydroxy-3'-tert-butyl-5'-(3"-methacryloxypropyl)phenyl]-5-methoxy-2H-benzotriazol:

.

In preferred embodiments, the implementation of UV chromophores of the present invention provide a cutoff transmittance over the wavelength of 385 and usually provide a cut-off in the short wavelength visible (410-430 nm) region of the electromagnetic spectrum. Then these chromophores can provide the desired protection of human tissues and/or the IOL material from UV radiation (<400 nm). The above benzotriazole are examples of such UV chromophores. As such, these UV chromophores can also be referred to as UV absorbers/short-wave visible light.

The materials of the devices of the present invention can also contain polymerized yellow dye, which reduces the blue light from the medium - to long-wavelength (430-500 nm). Such dyes and suitable UV chromophores described in owned by the same applicant of the patent application U.S. serial No. 11/871411, entitled "Intraocular Lenses with Unique Blue-Violet Cutoff and Blue Light Transmission Characteristics", filed October 12, 2007, which is fully incorporated here for all purposes.

what if not stated otherwise, "cut-off" means the wavelength at which the transmittance is not more than 1%. "1%cut-off" means the wavelength at which the transmittance is not more than 1%. "10%cutoff" means the wavelength at which the transmittance is not more than 10%.

As an additional benefit, it was found that these benzotriazole can be effective to resist degradation due to radiation even when used in relatively low concentrations. Thus, it is assumed that the effective number of benzotriazole in the hydrogel material is less than 3 mass%, more typically less than 1 mass% and even possibly less than 0.5% by weight of hydrogel material. The number of benzotriazole is typically more than about 0.02 mass%, and more typically more than about 0.1% by weight of hydrogel material. It should be understood, however, that these mass percent for resistant to radiation connections do not limit the number of resistant to radiation of a compound that can be used within the scope of the present invention, unless otherwise indicated.

Mainly, the use of benzotriazole formula (I), especially when used in lower concentrations, can give a hydrogel material or IOL increased ion permeability, increased RVS, increased ur the level of extractables. In preferred embodiments, the implementation of the hydrogel material of the present invention has a diffusion coefficient of ions (CBI), which is at least 15×10-7preferably, at least 17×10-7or at least 18×10-7and even possibly at least 20×10-7cm2/s at 35°C. it is Clear that the diffusion coefficient of the ions is a measure of ionic permeability. The above factors are given for the diffusion of chloride ions when using solutions of sodium chloride. The methodology for determining the diffusion coefficient of the ions is presented below.

Additionally or alternatively, the hydrogel material may have a percentage of RVS, which is at least 50%, more typically at least 53% and even possibly at least 55%. It is also assumed that the hydrogel material may have a percentage of extractable, of at least 13%. The percentage of RVS and the percentage of extractable determined according to the gravimetric methods. It should be noted that these values are the values before irradiation, however, these values will be increased after irradiation, especially in the case when the IOL material resists degradation from UV radiation.

The percentage of RVS can be defined for the present invention according to the following Protocol: 1) vzveshival the e hydrogel material in a completely or almost completely (i.e. less than 1% by weight of water) digidratirovannogo able to get digidrirovanny weight (Wd); 2) immersion hydrogel material in purified deionized water (e.g., vessel) for at least 24 hours at 37°C, in order to fully hydrate the material; and (3) weighing the fully hydrated material to get fully hydrated weight (Wh). Then use the following equation to determine the percentage of RVS:

the percentage of PBC=((Wh-Wd)/Wh)×100.

It should be understood that this type of protection from UV is particularly desirable for PC IOL Phakic. In particular, PC IOL Phakic are usually in the eye for extended periods of time (e.g. more than 6 months, a year, several years or more) in contrast, for example, disposable contact lenses. In fact, it is extremely desirable that these types of lenses had a long-term resistance to degradation caused by exposure to radiation. In addition, a particularly desirable to provide such protection hydrogel IOL PC Phakic because PC IOL Phakic usually placed in the posterior chamber of the eye with the natural lens of the eye, and hydrogel materials was one of the few materials suitable for use in this place. Such PC IOL Phakic will usually include, although not necessarily required, haptic cell battery (included) what you which are arranged at an angle to facilitate fixation of the IOL in the PC-camera.

In addition, as discussed above properties, especially the ionic permeability of the natural water circulation material to the eye may increase. This is especially important for PC IOL Phakic and may even allow the IOL of the present invention temporarily or more permanently in contact with the rear camera or stay on the natural lens of the eye, and not be far from that of the natural lens.

It is additionally assumed that the IOL of the present invention may include a number of additional or alternative ingredients, signs or other. Examples include, without limitation, materials, coatings, pharmaceuticals (therapeutic agent), functional groups on cell receptors, protein groups, regulating the viscosity of funds (for example, thickeners or thinners, solvents, combinations thereof or the like.

IOL of the present invention can be formed using several different methods or protocols. According to one preferred Protocol monomers (for example, comonomers) of the present invention, the curing agent and optionally a curing accelerator, resistant to radiation connection and any other desired ingredients combine the natural with the formation of masterbatches. Then uterine mixture is exposed to a stimulus (for example, environmental conditions such as heat or light (e.g. blue light), which initiates the polymerization and cross-linking monomers. Subjected to initiate masterbatches can be molded in a plate of the desired geometric shape and can be clamped in the clamping devices curing for the formation of the IOL.

Then cast plates usually utverjdayut by prolonged exposure to environmental conditions such as heat, light (e.g. blue light) or both. For example, in one embodiment, the cast plate is exposed to elevated temperature (e.g. about 70°C) during the first period of time (for example, approximately 2 hours), and then raised to a second temperature (for example, about 110°C) during the second period of time (e.g., at least 10 minutes). In the second exemplary embodiment, plate utverjdayut using blue light with a wavelength of about 405 nm to about 415 nm during the first period of time (for example, approximately 3 hours), and then subjected to exposure to elevated temperature (for example, about 110°C) during the second period of time (for example, approximately one hour). Preferably, initiation, curing, or both carry out the environment of low humidity (for example, less than 1 ppm water) with low oxygen content (less than 100 ppm).

Hydrogel materials formed in accordance with the present invention typically exhibit a relatively high refractive indices. The refractive index of the hydrogel material of the present invention at 25°C. is typically more than approximately 1,410, more typically more than about 1,415, even more typically more than 1,420 and maybe even more than 1.44 or more 1,47, when the refractive index of the material (fully hydrated) measured in accordance with BS EN ISO 11979-5:2000.

Applicants have specifically included the full contents of all cited references in this description. In addition, when an amount, concentration, or other value or parameter is given as either a range or the preferred range or a list of upper preferable values and lower preferable values, this should be understood as a special disclosing all ranges formed from any pair of any upper range limit or preferred value and any lower range limit or preferred value, regardless of whether disclosed whether the ranges separately. If there is any numerical range of values, unless otherwise indicated, this range is assumed to include its endpoints and all whole and fractional numbers within the range. It is not envisaged that the scope of the invention limited to the specific values that you specified when defining a range.

Other embodiments of the present invention will be obvious to experts in this area from consideration of the present description and the practical implementation of the present invention disclosed here. It is assumed that the present description and examples be considered only as exemplary, and the true scope and essence of the invention defined by the following claims and its equivalents.

Comparative examples

In table 1 below lists some of the compositions used to form hydrogels, which were tested to determine svetostoyjkostj or resistance to degradation by exposure to UV radiation:

64,50%
Table 1
NVPHEMAPEMAAMANMP (solvent)BHMAUV13bnzfneT21sLucerin TPO
A(entry checkpoints for important locations.)35,00%-0,50%10,00%---0,50%-
B35,00%59,00%-0,50%10,00%of 5.50%--0,50%-
C35,00%59,50%-0,50%10,00%to 5.00%--0,50%-
D35,00%60,00%-0,50%10,00%4,50%--0,50%-
E35,00%64,10% -0,50%10,00%-0,40%-0,50%-
F35,00%64,30%-0,50%10,00%-0,20%-0,50%-
G35,00%64,40%-0,50%10,00%-0,10%-0,50%-
H35,00%59,00%-0,50%10,00%--of 5.50%0,50%-
I35,00%59,50% -0,50%10,00%--to 5.00%0,50%-
J35,00%60,00%-0,50%10,00%--4,50%0,50%-
K69,88%-24,51%0,62%-to 5.00%--2,59%-
L69,70%-29,30%1,00%----1,00%1,00%
M69,65%-28,85% 1,00%--0,50%-1,00%1,00%
NVP - N-vinyl pyrrolidone
HEMA - 2-hydroxyethylmethacrylate
PEMA - poly(ethyl methacrylate)
AMA - alismataceae
NMP is N-methyl-2-pyrrolidone
BHMA - 2-[3-(2H-benzotriazol-2-yl)-4-hydroxyphenyl]ethyl methacrylate,
UV13 - 2-(2'-hydroxy-3'-tert-butyl-5'-(3"-methacryloyloxy)propoxyphenyl]-5-methoxy-2H-benzotriazol
bnzfne - 4-(2-acroloxidae)-2-hydroxybenzophenone
T21s - tert-BUTYLPEROXY-2-ethylhexanoate
Lucerin TPO - oxide, 2,4,6-trimethylbenzenesulfonyl

Songs include benzothiazolylsulfenamide (FNMA), substituted 2-hydroxyphenylacetate (UV-13) according to the above formula I or the benzophenone (bnzfne) as a UV chromophore. Referring to table 2 below, you can see that the samples with UV-13 provide a higher percentage of extractable higher RVS and more high ion permeability.

Table 2
Levels of extractable, RVS and ion permeability of UV materials PC Phakic
ID
(% of UV absorber (wt./wt.))
the former is R. (%)STD. off.The diffusion coefficient of ions
RVS (%)STD. off.D((cm2/sec)×10-7)STD. off.
Control (A)13,220,1155,730,0919,21,6
BHMA5.5 (B)12,100,1647,840,619,8-
BHMA5.0 (C)12,040,1748.38 per0,1110,2-
BHMA4.5 (D)12,190,3948,830,0710,6-
UV130.4 (E)to 13.090,670,0818,41,7
UV130.2 (F)13,300,1555,930,0621,72,6
UV130.1 (G)13,380,2755,860,2218,60,3
BNZFNE5.5 (H)12,740,1048,580,0712,1-
BNZFNE5.0 (I)12,640,2049,280,0715,3-
BNZFNE4.5 (J)12,630,2149,910,0217,4-

For comparison purposes, the test of UV radiation was applied to the test samples a and L, as well as samples of K and M. the Test Provo is or ISO 11979-5:2006 ophthalmic implants/intraocular lenses. After the test sample To demonstrated significant degradation due to the yellowing and a noticeable difference in the UV/visible spectra after the test at ~46 days exposure to ~100 W/m2UV-A at ~37°C, as provided in accordance with the ISO standard. In contrast, the samples that included UV-13 or not included UV chromophore, did not show similar degradation.

In addition, in table 3 below presents the results of measurements of the optical power in diopters for the sample (i.e. the sample without UV chromophore) and the sample is virtually identical to the sample (i.e. sample similar to sample A, but including UV 13), before exposure to UV, after 10 years of equivalent exposure to UV and after 20 years of equivalent effect.

Table 3
The results of measuring the optical power of materials PC Phakic after UV exposure
N=3 lens checkpoints for important locations.10 years each, N=3 lenses20 years old, N=6 lenses
Source.The checkpoints for important locations.The differenceSource.10 yearsThe difference Source.20 yearsThe difference
E UV13 0,5%-9,84-9,950,11-9,96-9,85-0,11-9,78-9,71-0,07
Article off.0,040,060,090,160,140,050,240,340,14
A-10,51-10,50-0,01-10,41-9,93-0,48-10,31-9,80-0,52
Article off.0,130,460,470,130,330,220,230,27 0,24

As you can see, the results of measuring the optical power for sample E did not change significantly, while the results of measuring the optical power on the sample And changed significantly. In fact, it appears that UV 13 serves to protect the IOL material from degradation by UV.

Measurement of diffusion coefficient of ions

The diffusion coefficients of ions for hydrogel materials of the present invention can be determined using a system with separation of solutions. In particular, the sample hydrogel material fitted between the first solution with a relatively high concentration of sodium chloride (NaCl) and the second solution with a relatively low concentration of NaCl or without NaCl. After that, use one or more of conductivity meters and probes conductivity for measuring changes in the conductivity of the first solution, second solution, or both. During such measurements, the first and second solutions must be constantly mixed and maintained at a temperature of 35°C. Then, the diffusion coefficient of ions (D) of the sample can be determined by relating the conductivity of the second solution with the diffusion coefficient of the ions, using the law of Fika and mass balance. In particular, the law Fika argues that the flow per unit area (J) is proportional to the concentration gradient (C), the measured p is erpendicular section (x), i.e.

J=-D(∂C/∂x).

The conservation of mass balance mathematically indicates that the increase in the concentration in one sample solution at time (t) must be equal to the decrease in the concentration of another solution, given the volume (V)related to each of the first and second solutions, ie,

Vh(dCh/dt)+V(dCl/dt)=0,

where the subscript h denotes the solution with a high concentration, and the subscript l denotes the solution with the lower concentration. Using these principles and methodologies, as well as skilled scientific calibration and rinsing, the specialist will be able to determine the diffusion coefficient of ions with a high degree of accuracy.

1. Ophthalmic device, comprising:
intraocular lens made with the possibility of introducing in the eye, and the eye has a front camera and rear camera, and a lens made according to the size and shape for insertion into the posterior chamber of the eye in the form of lenses PC Phakic, thus:
i. the lens is formed from a hydrogel material, which is formed of cross-linked polymer, and at least 60% by weight of this hydrogel material is a copolymer component formed from a first monomer selected from HEMA, PEMA, or both, and a second monomer that contains one or more monomers of N-vinylacetate; and
ii. the lens includes UV chromophore, and this UV chromophore includes benzur the azole according to the following formula:

for formula (A)
R1represents a substituted or unsubstituted C1-C6alkyl, halogen, OH, C1-C12alkyloxy, optionally substituted, phenoxy or optionally substituted, naphthyloxy, where the optional substituents are C1-C6alkyl, C1-C6alkoxy, OH, -(CH2CH2O)n- or -(CH2CH(CH3)O)n-;
R2represents a C1-C12alkyl, (CH2CH2O)n, (CH2CH(CH3)O)nor CH2CH2CH2(Si(CH3)2O)mSi(CH3)2CH2CH2CH2;
X is absent if R2represents (CH2CH2O)nor (CH2CH(CH3)O)notherwise X represents O, NR4or S;
R3absent or represents C(=O)C(=O)CjH2jC1-C6alkyl, phenyl or C1-C6alkylphenyl;
R4represents H or methyl;
R5represents H, C1-C6alkyl or phenyl;
R6represents H, C1-C12alkyl or C1-C12alkyloxy;
R7represents a C1-C6alkyl or is absent;
m is 1-9;
n is 2-10 and
j is 1-6;
while the equilibrium water contents (PBC) hydrogel is the first material is at least 50%.

2. Ophthalmologic device according to claim 1, and benzotriazol has the following formula:

this
R1represents halogen, OH, C1-C12alkyloxy, optionally substituted, phenoxy or optionally substituted, naphthyloxy, where the optional substituents are C1-C6alkyl, C1-C6alkoxy, OH, -(CH2CH2O)n- or -(CH2CH(CH3)O)n-;
R2represents a C1-C12alkyl, (CH2CH2O)n, (CH2CH(CH3)O)nor CH2CH2CH2(Si(CH3)2O)mSi(SH3)2CH2CH2CH2;
X is absent if R2represents (CH2CH2O)nor (CH2CH(CH3)O)notherwise X represents O, NR4or S;
R3absent or represents C(=O)C(=O)CjH2jC1-C6alkyl, phenyl or C1-C6alkylphenyl;
R4represents H or methyl;
R5represents H, C1-C6alkyl or phenyl;
R6represents H or C1-C12alkyl;
m is 1-9;
n is 2-10 and
j is 1-6.

3. Ophthalmologic device according to claim 1, and:
R1represents Cl, Br, C1-C4alkoxy or phenoxy;
R2/sub> represents a C1-C6alkyl;
X represents O or NR4;
R3represents C(=O) or C1-C6alkylphenyl;
R4represents H or methyl;
R5represents H and
R6represents a C4-C12t-alkyl.

4. Ophthalmologic device according to claim 1, and:
R1represents methoxy;
R2represents a C2-C3alkyl;
X represents O;
R3represents C(=O);
R4represents H or methyl;
R5represents H; and
R6represents t-butyl.

5. Ophthalmologic device according to claim 1, and UV chromophore is 2-{2'-hydroxy-3'-tert-butyl-5'-[3"-(4"'-vinylbenzoate)propoxy]phenyl}-5-methoxy-2H-benzotriazol:

or 2-[2'-hydroxy-3'-tert-butyl-5'-(3"-methacryloxypropyl)phenyl]-5-methoxy-2H-benzotriazol:

6. Ophthalmologic device according to any one of claims 1 to 5, with UV chromophore greatly enhances the stability of the lens to degradation under the action of electromagnetic radiation.

7. Ophthalmologic device according to claim 1, with the cross-linked polymer is a copolymer of NVP and methacrylate.

8. Ophthalmologic device according to claim 1, with the cross-linked polymer includes NVP-co-is hydroxyethylacrylate, NVP-co-allmaterial or a combination thereof.

9. Ophthalmologic device according to any one of claims 1 to 5, the hydrogel material has a refractive index that is at least 1,4.

10. Ophthalmologic device according to any one of claims 1 to 5, the hydrogel material includes at least 0.02 percent by weight, but less than 1% by weight of a UV chromophore.

11. Ophthalmic device of claim 10, with the hydrogel material includes less than 0.5% by weight of a UV chromophore.

12. Ophthalmologic device according to any one of claims 1 to 5, and the diffusion coefficient of ions hydrogel material is at least 17×10-7cm2/s at 35°C.



 

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