U.S. patent application number 13/076665 was filed with the patent office on 2011-10-06 for adjustable chromophore compounds and materials incorporating such compounds.
Invention is credited to Joseph I. Weinschenk, III.
Application Number | 20110245818 13/076665 |
Document ID | / |
Family ID | 44148789 |
Filed Date | 2011-10-06 |
United States Patent
Application |
20110245818 |
Kind Code |
A1 |
Weinschenk, III; Joseph I. |
October 6, 2011 |
ADJUSTABLE CHROMOPHORE COMPOUNDS AND MATERIALS INCORPORATING SUCH
COMPOUNDS
Abstract
The present invention is directed to adjustable chromophore
compounds and materials (e.g., ophthalmic lens materials)
incorporating those compounds. The adjustable chromophore compounds
include a chemical moiety that structurally changes upon exposure
to predetermined electromagnetic radiation (e.g., two photon
radiation) as well as lens materials, particularly intraocular lens
materials that incorporate those compounds.
Inventors: |
Weinschenk, III; Joseph I.;
(Fort Worth, TX) |
Family ID: |
44148789 |
Appl. No.: |
13/076665 |
Filed: |
March 31, 2011 |
Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
|
|
61320442 |
Apr 2, 2010 |
|
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Current U.S.
Class: |
606/4 ; 252/586;
548/261 |
Current CPC
Class: |
B29D 11/00461 20130101;
B01J 19/123 20130101; C08K 5/3475 20130101; G02B 1/043 20130101;
B01J 19/127 20130101; C07D 249/20 20130101; A61L 2430/16 20130101;
C08L 33/08 20130101; C08L 33/08 20130101; G02B 1/043 20130101; A61L
27/50 20130101; C08K 5/3475 20130101 |
Class at
Publication: |
606/4 ; 548/261;
252/586 |
International
Class: |
A61F 9/007 20060101
A61F009/007; C07D 249/20 20060101 C07D249/20; G02B 5/23 20060101
G02B005/23 |
Claims
1. An adjustable chromophore comprising: a compound of the formula:
B--X; wherein: v) B is a base chromophore compound; and vi) X is an
adjustable chemical moiety that forms a remaining chemical moiety
(C) upon exposure to predetermined electromagnetic radiation
thereby forming the compound: B--C; vii) the compound B--C provided
greater light absorption than the compound B--X; and viii) the
remaining chemical moiety (C) includes a conjugated double
bond.
2. A chromophore as in claim 1 wherein the base chromophore
compound is selected from the group consisting of benzotriazoles,
benzophenones, azo dyes and cinnamate esters.
3. A chromophore as in claim 2 wherein the base chromophore
compound is a benzotriazole.
4. A chromophore as in claim 1 wherein the compound B--C absorbs a
significant amount of UV light, blue light or both.
5. A chromophore as in claim 3 wherein the compound B--C absorbs a
significant amount of blue light.
6. A chromophore as in claim 1 wherein the adjustable chemical
moiety X is a cyclic moiety.
7. A chromophore as in claim 1 wherein the adjustable chemical
moiety X is dicyclopentadiene.
8. A lens comprising: a polymeric material; and the adjustable
chromophore compound of claim 1 distributed within the polymeric
material; wherein the material can absorb light at progressively
greater wavelengths as greater amounts of the compound B--C are
formed from the adjustable compound B--X.
9. A method of adjusting a lens in vivo or in vitro comprising:
directing the predetermined electromagnetic radiation at the
polymeric material of claim 8 to form the compound B--C either
prior to or after implantation of the lens in the eye.
10. An adjustable chromophore system, comprising: a compound of the
formula: B--X or B--C as part of the reactive system:
B--X.revreaction.B--C wherein: i) B is a base chromophore compound;
ii) X is an adjustable chemical moiety that forms remaining
chemical moiety (C) upon exposure to first predetermined
electromagnetic radiation thereby forming the compound B--C; iii)
the compound B--C provides greater light absorption than the
compound B--X; iv) the remaining chemical moiety (C) includes a
conjugated double bond; and v) optionally, the compound B--C forms
the compound B--X upon exposure to second predetermined
electromagnetic radiation either with or without the aid of a
separable group (S).
11. A system as in claim 10 wherein the base chromophore compound
is selected from the group consisting of benzotriazoles,
benzophenones, azo dyes and cinnamate esters.
12. A system as in claim 11 wherein the base chromophore compound
is a benzotriazole.
13. A system as in claim 10 wherein the compound B--C absorbs a
significant amount of UV light, blue light or both.
14. A system as in claim 10 wherein the compound B--C absorbs a
significant amount of blue light.
15. A system as in claim 10 wherein the adjustable chemical moiety
X is a cyclic moiety.
16. A system as in claim 10 wherein the adjustable chemical moiety
X is dicyclopentadiene.
17. A lens comprising: a polymeric material; and the adjustable
chromophore system of claim 10 distributed within the polymeric
material.
18. A method of adjusting a lens in vivo or in vitro comprising:
directing the predetermined first or second electromagnetic
radiation at the lens of claim 17 to form the compound B--C or B--X
either prior to or after implantation of the lens in the eye.
19. An adjustable chromophore system, comprising: a compound of the
formula: B--X or B--C as part of the reactive system:
B--X.revreaction.B--C wherein: i) B is a base chromophore compound;
ii) X is an adjustable chemical moiety that forms remaining
chemical moiety (C) upon exposure to first predetermined
electromagnetic radiation thereby forming the compound B--C; iii)
the compound B--C provides greater light absorption than the
compound B--X; iv) the remaining chemical moiety (C) includes a
conjugated double bond; v) the compound B--C forms the compound
B--X upon exposure to second predetermined electromagnetic
radiation either with or without the aid of a separable group (S);
vi) the base chromophore compound is selected from the group
consisting of benzotriazoles, benzophenones, azo dyes and cinnamate
esters; vii) the compound B--C absorbs a significant amount of UV
light, blue light or both; and viii) the adjustable chemical moiety
X is a cyclic moiety.
20. A lens comprising: a polymeric material; and the adjustable
chromophore system of claim 19 distributed within the polymeric
material.
21. A method of adjusting a lens in vivo or in vitro comprising:
directing the predetermined first or second electromagnetic
radiation at the lens of claim 20 to form the compound B--C or B--X
either prior to or after implantation of the lens in the eye.
Description
CROSS REFERENCE TO RELATED APPLICATION
[0001] This application claims priority under 35 U.S.C. .sctn.119
to U.S. Provisional Patent Application Ser. No. 61/320,442, filed
Apr. 2, 2010, the entire contents of which are incorporated herein
by reference.
TECHNICAL FIELD OF THE INVENTION
[0002] The present invention is related to adjustable chromophore
compounds and materials (e.g., ophthalmic lens materials)
incorporating those compounds. More particularly, the present
invention is related to adjustable chromophore compounds that
includes a chemical moiety that structurally changes upon exposure
to predetermined electromagnetic radiation (e.g., two photon
radiation) as well as lens materials (e.g., intraocular lens
materials) that incorporate those compounds.
BACKGROUND OF THE INVENTION
[0003] Chromophore compounds are molecules that absorb light and
such light absorption is desirable for a wide range of products.
They are particularly important and useful in lenses of many
different types. As examples, chromophores have been incorporated
into lenses of sunglasses, lenses of spectacles, contact lenses and
intraocular lenses (IOLs). As such, a significant amount of
research has been performed investigating a wide variety of
compounds with light absorption characteristics.
[0004] It is typical for lenses such as those mentioned above to be
formed of polymeric or glass matrices. Advantageously, the
chromophores can be dispersed or distributed throughout portions or
the entirety of the matrices and the concentrations of the
chromophores can be substantially homogeneous throughout the
matrices or the concentrations can be varied in certain portions of
the matrices.
[0005] For lenses, the amount and type (e.g., wavelength) of light
absorption provided by any particular chromophore typically depends
upon the amount and type (e.g., chemical structure) of chromophore
used in a particular lens. This type and amount of chromophore is
typically predetermined and provides the lens with a particular
predetermined light absorption profile. While this is generally
acceptable for most lenses, there are circumstances in which it may
be desirable to change the absorption characteristics of a
chromophore after it has been incorporated into a lens thereby
changing the absorption profile provided by the lens itself.
[0006] As one example, individuals having intraocular lens (IOLs)
may be particularly desirous of having the ability to change the
absorption profile provided by the chromophores in their lenses.
Individuals that will be exposed to greater amounts of sunlight due
to geographical changes, activity (e.g., employment) changes or
other changes in their lives may desire a change in the absorption
profile of their IOLs. Individuals that have or develop sensitivity
to particular wavelengths of light may desire a change in the
absorption profile. It would also be desirable to be able to tune
the absorption profile of an IOL for all individuals receiving
IOLs.
[0007] It is also the case that some chromophore compounds tend to
degrade over time due to absorption of light. In this circumstance,
it would be desirable to be able to adjust the absorption profile
of the lens to compensate for the degradation of the
chromophores.
[0008] In view of the above, it would be particularly desirable to
provide a chromophore with adjustable light absorption
characteristics. It would also be particularly desirable to provide
such chromophore compound within a product (e.g., lens) wherein the
absorption profile of the lens could be adjusted after
incorporation of the chromophore compound into the lens.
SUMMARY OF THE INVENTION
[0009] In one embodiment, the present invention is directed to an
adjustable chromophore comprising a compound of the formula:
B--X;
[0010] wherein: [0011] i) B is a base chromophore compound; and
[0012] ii) X is an adjustable chemical moiety that forms a
remaining chemical moiety (C) upon exposure to predetermined
electromagnetic radiation thereby forming the compound:
[0012] B--C; [0013] iii) the compound B--C provided greater light
absorption than the compound B--X; and [0014] iv) the remaining
chemical moiety (C) includes a conjugated double bond.
[0015] The present invention is also directed to a lens comprising
a polymeric material and the adjustable chromophore compound, as
described herein, distributed within the polymeric material. The
material that includes the chromophore compound can typically
absorb light at progressively greater wavelengths as greater
amounts of the compound B--C are formed from the adjustable
compound B--X.
[0016] The present invention is also directed to a method of
adjusting a lens in vivo or in vitro. The method includes directing
predetermined electromagnetic radiation as described herein at the
above described lens to form the compound B--C either prior to or
after implantation of the lens in the eye.
[0017] The present invention is also directed to an adjustable
chromophore system, comprising a compound of the formula:
B--X or B--C
[0018] as part of the reactive system:
B--X.revreaction.B--C
[0019] wherein: [0020] i) B is a base chromophore compound; and
[0021] ii) X is an adjustable chemical moiety that forms remaining
chemical moiety (C) upon exposure to first predetermined
electromagnetic radiation thereby forming the compound B--C: [0022]
iii) the compound B--C provides greater light absorption than the
compound B--X; and [0023] iv) the remaining chemical moiety (C)
includes a conjugated double bond; and [0024] v) optionally, the
compound B--C forms the compound B--X upon exposure to second
predetermined electromagnetic radiation either with or without the
aid of a separable group (S).
[0025] The base chromophore of the lens, the system or the
adjustable chromophore is preferably selected from the group
consisting of benzotriazoles, benzophenones, azo dyes and cinnamate
esters. The compound B--C typically absorbs a significant amount of
UV light, blue light or both. Moreover, the adjustable chemical
moiety X is a preferably a cyclic moiety such as
dicyclopentadiene.
BRIEF DESCRIPTION OF THE DRAWINGS
[0026] FIGS. 1A and 1B are respectively, a top and sectional view
of a contact lens in accordance with an aspect of the present
invention.
[0027] FIGS. 2A and 2B are respectively, a top and sectional view
of an intraocular lens in accordance with an aspect of the present
invention.
DETAILED DESCRIPTION OF THE INVENTION
[0028] The present invention is predicated upon the provision of an
adjustable chromophore compound and/or system. The absorption
characteristics (e.g., absorption profile) of the chromophore
compound will be adjustable upon exposure to predetermined
electromagnetic radiation. The present invention is also predicated
upon the provision of products, particularly lenses (e.g., lens of
sunglasses, lenses of spectacles, IOLs, contact lenses or the
like), that incorporate the adjustable chromophore compounds and/or
system of the present invention such that the absorption profile of
those products can be adjusted.
[0029] The adjustable chromophore compound will typically have the
following chemical structure:
B--X
wherein: B is a base chromophore compound; and X is an adjustable
chemical moiety that forms a separable group (S) and a remaining
chemical moiety (C) upon exposure to the predetermined
electromagnetic radiation thereby forming the compound:
B--C;
Typically, the remaining chemical moiety (C) includes a conjugated
double bond. Advantageously, such conjugated double bond provides
significant adjustment to the absorption characteristics (e.g.,
absorption profile) of resultant chromophore compound B--C relative
to the adjustable chromophore compound B--X.
[0030] A great number of chromophores are known and may be used as
the base chromophore compound (B). In a preferred embodiment,
however, the base chromophore compound is selected from the group
consisting of benzotriazoles, benzophenones, azo dyes and cinnamate
esters. In a highly preferred embodiment the base chromophore
compound is a benzotriazole or benzophenone, but is most typically
a benzotriazole. Examples of benzotriazoles suitable as the base
chromophore compound are disclosed in U.S. Pat. Nos. 4,528,311 and
7,396,942; and U.S. Patent Application Nos. 2010/0012889 and
2008/0090937, all of which are fully incorporated herein in their
entirety by reference for all purposes. Other examples of
potentially suitable base chromophore compounds are disclosed in US
Patent Application Publication Nos.: 2007/0077214; 2008/0242818;
and 2002/0025401, all of which are fully incorporated herein in
their entirety by reference for all purposes.
[0031] The adjustable chemical moiety (X) can be any moiety that
can be separated into the remaining chemical moiety (C) and the
separable group (S) upon exposure to the predetermined
electromagnetic radiation. Typically, the chemical moiety (X) is
cyclical and, upon separation into the chemical moiety (C) and the
separable group (S), provides the chemical moiety (C) with a
conjugated double bond. Schematically, such a reaction would be as
follows:
X.fwdarw.C+S
Or
##STR00001##
Examples of moieties suitable for use as the adjustable chemical
moiety (X) include, without limitation, dicyclopentadiene,
dicyclohexadiene, cyclobutane, cyclohexene or the like. It shall be
understood that the structures of the chemical moiety (C) and the
separable group (S) will be dictated by the structure of the
chemical moiety (X) and, in certain circumstance, vice-versa. It
will also be understood that the separable group (S) could be bound
within a polymer matrix of the polymer, could be entangled in the
polymer matrix, but may not be either.
[0032] The adjustable chromophore system of the present invention
includes an adjustable chromophore compound of the present
invention and that adjustable chromophore compound can be adjusted
to the resultant chromophore compound is B--C but that adjustment
is then reversible such that the resultant chromophore compound
B--C can be adjusted back to the adjustable compound B--X. Thus,
the adjustable chromophore system includes a compound of the
formula:
B--X,B--C or both
as part of the reactive system:
B--X.revreaction.B--C+S
wherein: B is the base chromophore compound; and X is the
adjustable chemical moiety that forms separable group (S) and
remaining chemical moiety (C) upon exposure to a first
predetermined electromagnetic radiation thereby forming the
compound B--C where the remaining chemical moiety (C) includes a
conjugated double bond. It is then possible that the separation of
the adjustable chemical moiety (X) into the remaining chemical
moiety (C) and the separable group (S) may be reversible upon
exposure to a different predetermined electromagnetic radiation to
form the compound B--X. In such instance, the system will be able
to add to the level of absorption provided by the system or
subtract from the amount of absorption provided by the system
depending upon the electromagnetic radiation provided thereto.
[0033] The chromophore compound B--X and chromophore compound B--C
can include an electron donating chemical moiety (D), an electron
withdrawing chemical moiety (W) or both and those moieties will
typically remain with the chromophore compound B--C after the
adjustable moiety (X) is separated into the remaining moiety (C)
and the separable group (S). The donating moiety (D) and the
withdrawing moiety (W) can be part of the base chromophore compound
(B), the adjustable chemical moiety (X) and/or the remaining
chemical moiety (C). Typically, if the donating moiety (D) is part
of the base chromophore compound (B), then the withdrawing moiety
(W) is part of the adjusting chemical moiety (X) and the remaining
chemical moiety (C) and vice versa.
[0034] A variety of suitable electron withdrawing moieties (W) will
be evident to the skilled artisan. Examples of suitable electron
withdrawing moieties (W) include cyano groups, carbonyls, esters,
amides, sulfonyls, halogens, combinations thereof or the like. In a
preferred embodiment, the withdrawing moiety (W) is a halogen
(e.g., a halogen itself or a halogen inclusive group) such as
fluorine (F), chlorine (Cl), carbon trifluoride (CF.sub.3) or the
like. A variety of suitable electron donating moieties (D) will
also be evident to the skilled artisan. Examples of suitable
donating moieties (D) include, without limitation, alkyl groups
such as methyl groups and ethyl groups, alkoxy groups, amino groups
or the like.
[0035] Advantageously, the donating moiety (D), the withdrawing
moiety (W) or both can aid in polarizing the chromophore compound
B--C. Such polarization can aid the ability of the chromophore
compound B--C in absorbing light, particularly additional
wavelengths of light (e.g., higher or longer wavelengths of light).
Moreover, such polarization can be significantly blocked by the
adjustable chemical moiety (X) such that the light absorption
ability of the chromophore compound B--X is significantly reduced
(e.g., can be less than 80% or even 60%) relative to the light
absorbing ability of the chromophore compound B--C.
[0036] The adjustable moiety (X) can additionally or alternatively
include a mobilization inhibiting moiety (Z) and that moiety will
typically remain with the separable group (S) after the adjustable
moiety (X) is separated into the remaining moiety (C) and the
separable group (S). Such a mobilization inhibiting moiety (Z) is
particularly useful for situation where the chromophore compound
B--X is incorporated into a matrix (e.g., a polymer or glass
matrix) for maintaining the separable group (S) in the matrix after
the adjustable moiety (X) is separated into the remaining moiety
(C) and the separable group (S). Typically, the mobilization
inhibiting moiety is capable of entangling in the matrix.
Preferably, the mobilization inhibiting moiety (Z) is or includes a
substituted or unsubstituted alkyl group (e.g., an alkane chain)
with a carbon chain or carbon based group having a carbon atoms in
the range of C.sub.4-C.sub.20, more typically C.sub.5-C.sub.12 and
even possibly C.sub.6-C.sub.10.
[0037] The chromophore compounds and/or system of the present
invention can be incorporated into a variety of different products.
Most significantly, however, they can be incorporated into lenses
of products such as sunglasses or spectacles or into contact lenses
or IOLs. The chromophore compounds and system can be incorporated
into these lenses whether they are formed of glass or polymeric
material or a combination thereof. Typically, these materials,
whether thermoset or thermoplastic, will form a matrix and the
compounds and/or system can be distributed or dispersed throughout
the entirety or a portion of the matrix.
[0038] The chromophore compounds and/or system of the present
invention can be incorporated into matrices of materials commonly
used to form sunglasses or spectacles. Such materials can include
glass or polymeric materials such as polystyrene, polycarbonate,
acrylics, combinations thereof or the like.
[0039] The chromophore compounds and/or system of the present
invention can be incorporated into contact lenses, IOLs or both.
Contact lenses and IOLs typically includes matrices formed of
acrylate based materials (i.e., materials that are formed of at
least 20%, at least 50% or more acrylate monomers such as
phenylethyl methacrylate and hydroxyethyl methacrylate), silicone
materials or the like. The skilled artisan will understand that
chromophore compounds generally have been included in these types
of lenses and/or matrices and the chromophore compounds of the
present invention can be incorporated in a similar manner.
[0040] The adjustment of the chromophore compound of the present
invention can occur prior to incorporation into a product or
material matrix, but preferably occurs thereafter. As suggested,
the adjustment is caused by exposure of the chromophore compounds,
particularly the adjustable moiety (X) to predetermined
electromagnetic radiation. The particularly radiation employed to
form the adjustable moiety (X) into the remaining moiety (C) and
the separable group (S), or vice versa, will depend upon the
chemical structure of those groups and/or moieties. That
electromagnetic radiation can be from the visible part of the
electromagnetic spectrum or from the non-visible part of the
electromagnetic spectrum. In preferred embodiments, the
predetermined electromagnetic radiation is provided as relatively
intense ultraviolet (UV) radiation. In another preferred
embodiment, the predetermined radiation is provided as infrared
(IR) radiation. In one particularly preferred embodiment, the
electromagnetic radiation is provided as two-photon radiation that
is typically from the visible portion of the electromagnetic
spectrum. Advantageously, the two photon radiation can be provided
as light from the visible portion of the electromagnetic
spectrum.
[0041] The predetermined electromagnetic radiation is provided from
a light source such as a laser or other light or energy source that
can direct the radiation at the chromophores or at the materials
into which the chromophores have been incorporated. Most commonly,
the predetermined electromagnetic radiation will have a wavelength
and/or frequency configured to result in the following reaction
scheme:
B--X.fwdarw.B--C+S
wherein the adjustable chromophore compound B--X is exposed to the
predetermined radiation to produce the chromophore compound B--C
and the separable group (S). Moreover, within the system of the
present invention, a second predetermined electromagnetic radiation
will have a wavelength and/or frequency configured to cause the
reversal of that reaction.
[0042] It will also be understood, particularly with reference to
Example 4 below, that the chromophore compound B--X can be
converted directly to B--C without the formation of a separable
group. This scheme can occur, as it does in Example 4, according to
the following reaction scheme:
B--X--B.revreaction.B--C+B--C
Alternatively, the chemical entity which would normally be the
separable group (S) might be or become chemically bonded with and
be part of the base chromophore such that system of the present
invention could occur according to the following scheme:
B--X.revreaction.B--C
[0043] In this invention, the chromophore compound B--C will
typically provide a significantly greater amount of light
absorption than the adjustable chromophore compound B--X. Moreover,
it is possible and often desirable that, as more of the chromophore
compound B--C is formed, greater amounts of light at greater
wavelengths are absorbed. In this scenario, the absorption cutoff
of the material that include the chromophore compound B--C will
move toward progressively higher wavelengths as more and more of
the chromophore compound B--C is formed.
[0044] As a quantification of this change in absorption, it is
desirable for a material including compound B--X to absorb at least
80% of light at a first wavelength and less than 20% of light at a
second wavelength when less than 25% of a starting amount or
concentration of compound B--X has been converted to compound B--C
and separable group (S), but for the material to absorb at least
80% of light at the first wavelength and at least 80% of light at
the second wavelength after at least 75% of the starting amount or
concentration of the compound B--X has been converted to compound
B--C. In such a situation, the first wavelength is at least 5
nanometers, more preferably at least 10 nanometers and even
possibly at least 15 nanometers less than the second
wavelength.
[0045] As suggested above, it is also contemplated that the
chromophore compound B--C and separable group (S) can be exposed to
predetermined radiation to produce adjustable chromophore compound
B--X. As a quantification of this absorption, it is desirable for a
material including compound B--C and separable group (S) to absorb
at least 80% of light at a first wavelength and light at a second
wavelength when less than 25% of a starting amount or concentration
of compound B--C and separable group (S) has been converted to
compound B--X but for the material to absorb at least 80% of light
at the first wavelength but less than 20% of light at the second
wavelength after at least 75% of the starting amount or
concentration the compound B--C and the separable group (S) has
been converted to compound B--X. In such a situation, the first
wavelength is at least 5 nanometers, more preferably at least 10
nanometers and even possibly at least 15 nanometers less than the
second wavelength.
[0046] For ophthalmic lenses, particularly IOLs and/or contact
lenses, the chromophores B--X and/or B--C are typically designed to
provide substantial absorption (e.g., at least 50% and even at
least 80%) of light at wavelengths in the UV range up to and even
into portions of the blue light range. As such, the first and
second wavelengths, as discussed above, will typically be in the UV
to blue portions of the electromagnetic spectrum. Thus, in
preferred embodiments, the first and second wavelengths are both
preferably in the range of 300 to 500, more preferably 380 to 470
and even more preferably 390 to 440 nanometers.
[0047] The skilled artisan will understand that the IOLs and
contact lenses that will receive the chromophore compounds of the
present invention will be sized and shaped suitably for application
to the eye. With reference to FIGS. 1A and 1B, a contact lens 10
will typically have a largest outer perimeter (e.g., largest
peripheral circumference) 12 of at least 2, more typically at least
3 and even more typically at least 4 centimeters. The largest
perimeter 12 will also typically be less than 10, more typically
less than 6 and even more typically less than 5.5 centimeters. The
contact lens will also typically include a concave surface 14
opposing a convex surface 16. With reference to FIGS. 2A and 2B, an
IOL 20 will typically have a largest outer perimeter (e.g., largest
peripheral circumference) 22 of at least 1.5, more typically at
least 2.0 and even more typically at least 3.2 centimeters. The
largest perimeter 22 will also typically be less than 7, more
typically less than 5 and even more typically less than 4.5
centimeters. Aphakic IOLs will also typically include a first
convex surface 24 opposing a second convex surface 26 whereas
phakic IOLs may have convex surfaces like the aphakic IOLs or
convex/concave surfaces like the contact lenses.
[0048] While these absorption adjustments can occur in vitro, it is
also contemplated that they may occur in vivo. For example, and
without limitation, both contact lenses and IOLs may be adjusted
after application or implantation of those lenses to a mammalian
eye, particularly a human eye. This is particularly the case where
visible light (e.g., two photon light) is used to adjust the
absorption characteristics. A discussion of techniques of using two
photon light to adjust refractive index of implanted IOLs is
provided in US Patent Publication No. 2009/0157178, which is fully
incorporated herein by reference for all purposes. Advantageously,
such techniques might also be used to adjust the chromophores of
the present invention.
[0049] As a further advantage of the present invention, the
predetermined radiation can be directed at particular portions of
the lens to enhance light absorption in particular pre-selected
regions of the lens while other regions of the lens will exhibit
less absorption. For an IOL, for example, it might be desirable to
enhance the light absorption of a nucleus portion of the IOL while
leaving the peripheral portion of the IOL to exhibit less light
absorption. Such an IOL would then exhibit the greater light
absorption when light is bright and the pupil of the eye is small
and would exhibit less absorption when there is less light and the
pupil of the eye is larger. In such an embodiment, the nucleus
region will typically have a concentration of the chromophore
compound B--C that is greater than 120% and more typically greater
than 150% of the concentration at a peripheral region of the lens.
Such nucleus regions and such peripheral regions will both be at
least 10% of the overall volume of the IOL excluding any
haptics.
EXAMPLES
Example 1
##STR00002##
[0050] Example 1 above illustrates one exemplary embodiment of the
invention. As can be seen, a chromophore compound B--X includes a
benzotriazole base chromophore
[0051] (B) and an adjustable moiety (X), which is a
dicyclopentadiene. The adjustable moiety (X) includes a
mobilization inhibiting group (Z), which is preferably an alkane
chain, and an electron donating moiety (D), which is preferably an
alkoxy group. The base chromophore compound (B) includes an
electron withdrawing group (W), which is preferably one of the
halogen or halogenated groups discussed above. As can be seen, upon
exposure to predetermined radiation, the chromophore compound B--X
becomes the chromophore compound B--C and separable group (S) with
the chromophore compound B--C having a conjugated double bond and
the electron donating group (D) as well as the remaining group (C).
The base chromophore (B) then includes the electron withdrawing
group (W). Further, the separable group (S) includes the
mobilization inhibiting group (Z).
Example 2
##STR00003##
[0052] Example 2 above illustrates another exemplary embodiment of
the invention. As can be seen, a chromophore compound B--X includes
a benzotriazole base chromophore (B) and an adjustable moiety (X),
which is a dicyclopentadiene. The adjustable moiety (X) includes a
mobilization inhibiting group (Z), which is preferably an alkane
chain, and an electron withdrawing moiety (W), which is preferably
a halogen group. The base chromophore compound (B) includes an
electron donating group (D), which is preferably an alkoxy group.
As can be seen, upon exposure to predetermined radiation, the
chromophore compound B--X becomes the chromophore compound B--C and
separable group (S) with the chromophore compound B--C having a
conjugated double bond and the electron withdrawing group (W) as
well as the remaining group (C). The base chromophore (B) then
includes the electron donating group (D). Further, the separable
group (S) includes the mobilization inhibiting group (Z).
Example 3
##STR00004##
[0053] Example 3 above illustrates another exemplary embodiment of
the invention. As can be seen, a chromophore compound B--X includes
a benzotriazole base chromophore (B) and an adjustable moiety (X),
which is a dicyclopentadiene. In this example, a cyclic moiety of
the base chromophore (B) and the dicyclopentadiene share a common
bond. The adjustable moiety (X) includes a mobilization inhibiting
group (Z), which is preferably an alkane chain. Further, the base
chromophore (B) includes an electron withdrawing moiety (W), which
is preferably a halogen group and an electron donating group (D),
which preferably includes an alkoxy group. As can be seen, upon
exposure to predetermined radiation, the chromophore compound B--X
become the chromophore compound B--C and separable group (S) with
the chromophore compound B--C having a conjugated double bond as
the remaining group (C) and the electron withdrawing group (W). The
base chromophore (B) also includes the electron donating group (D).
Further, the separable group (S) includes the mobilization
inhibiting group (Z).
Example 4
##STR00005##
[0054] Example 4 above illustrates another exemplary embodiment of
the system of the invention. As can be seen, a pair of base
chromophore compounds (B), which are both benzotriazoles are both
bonded to a single adjustable moiety (X), which is a cyclobutane,
to form the compound B--X--B. Each of the base chromophore
compounds (B) include both an electron withdrawing moiety (W),
which is preferably a halogen group and an electron donating group
(D), which preferably includes an alkoxy group. As can be seen,
upon exposure to predetermined radiation, the chromophore compound
B--X--B becomes two separate chromophore compounds B--C with each
of the chromophore compounds B--C having a remaining group (C) with
a conjugated double bond. Moreover, upon exposure to a second
predetermined radiation, the chromophore compounds B--C can be
reacted to become the single chromophore compound B--X--B.
[0055] Applicants specifically incorporate the entire contents of
all cited references in this disclosure. Further, when an amount,
concentration, or other value or parameter is given as either a
range, preferred range, or a list of upper preferable values and
lower preferable values, this is to be understood as specifically
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 ranges are separately disclosed. Where a
range of numerical values is recited herein, unless otherwise
stated, the range is intended to include the endpoints thereof, and
all integers and fractions within the range. It is not intended
that the scope of the invention be limited to the specific values
recited when defining a range.
[0056] Other embodiments of the present invention will be apparent
to those skilled in the art from consideration of the present
specification and practice of the present invention disclosed
herein. It is intended that the present specification and examples
be considered as exemplary only with a true scope and spirit of the
invention being indicated by the following claims and equivalents
thereof.
* * * * *