CN101663053A - Have unique indigo plant-purple by with the intraocular lens of blue light transmissison characteristic - Google Patents

Have unique indigo plant-purple by with the intraocular lens of blue light transmissison characteristic Download PDF

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CN101663053A
CN101663053A CN200780038094A CN200780038094A CN101663053A CN 101663053 A CN101663053 A CN 101663053A CN 200780038094 A CN200780038094 A CN 200780038094A CN 200780038094 A CN200780038094 A CN 200780038094A CN 101663053 A CN101663053 A CN 101663053A
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ocular devices
formula
devices material
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D·L·金克尔森
J·I·魏因申克三世
M·卡拉克勒
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Novartis AG
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Alcon Universal Ltd
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Abstract

The invention discloses ocular devices material with improved optical transmission characteristics.This material comprises the combination of certain UV absorbent and blue light absorption chromophore.

Description

Have unique indigo plant-purple by with the intraocular lens of blue light transmissison characteristic
Technical field
The present invention relates to improved ocular devices material.Especially, the present invention relates to have the implantable ophthalmic lenses of improved optical transmission characteristics.
Background technology
Past, benzotriazole UV absorbers, for example oMTP (chemical compound 1) is added in intraocular lens (IOL) material, with the UV radiation in the protective environment.In general, the UV absorbent has polymerisable residue in its chemical constitution, for example vinyl, acrylic or methacrylic acid official can so that when polymerization, be covalently bound in the IOL material.According to concentration, these benzotriazole UV absorbers of great majority provide 1 to 10% UV transmission to end in the 390-410 nanometer range.
Figure G200780038094XD00011
Chemical compound 1
Recently, also in IOL, add polymerisable weld, to absorb deleterious blue ray radiation.As seen United States Patent (USP) 5,470,932 and 5,543,504 for example.Most of welds absorb blue light in wide wave-length coverage, and make common blue light in 500 to 400 nanometers progressively weaken according to the concentration of used weld.If transmitted spectrum is precipitous by being desirable in indigo plant-purple zone, so conventional weld can not provide precipitous ending in this zone.As seen US 2005/0243272, and it discloses the ocular devices of the purple light transmission filter disc with high selectivity, this filter disc optionally about 400 nanometers of wavelength-filtered to the light of about 450nm, but seldom absorption or absorbing wavelength be not higher than the light of 450 nanometers.
Brief summary of the invention
Developed and be especially suitable for use as IOL, also can be used as the ocular devices material of other ocular devices (for example contact lens, artificial cornea or corneal ring or corneal inlay).These materials comprise the combination of specific UV absorbent and polymerizable weld.Compare with the crystalline lens of mankind's nature, these materials have improved optical transmission characteristics, particularly at short wavelength's blue light region.
By using specific benzotriazole UV absorbers and, can change the optical absorption characteristics of IOL in conjunction with the polymerizable weld, with provide indigo plant-purple by (in the 400-430 nanometer range～1%T), and provide the transmission of the blue light that weakens 500 to 400 nanometers.Material of the present invention has following optical transmission characteristics (based on " plate " material sample of rectangular film or thick about 0.8-1 millimeter).They will have transmission and end in the indigo plant-purple zone (400-440 nanometer) of UV-visible spectrum.This indigo plant-purple is by being to characterize by the wavelength that is reached for 1% and 10% transmission value.Therefore, by being 410 to 430 nanometers, end for 10%T is 420 to 440 nanometers to preferred indigo plant-purple cutoff wavelength for 1%T.Preferred indigo plant-purple also is provided in the table 1 by scope.
By in-transmissison characteristic of blue region (440-460 nanometer) need be in the transillumination (＞70%) and the conversion of the major part between the absorbing light of high level.Transmission range for 440,450 and 460 nanometers is listed in the table 1.In this scope, motility can be arranged, thus can be approaching with youthful crystalline lens, maybe can provide maximum protection to the impaired patients'benefit of retinal function.
At last, high transmission part (470-500 nanometer) is the scope of blue light region, in this scope, allows more light transmission to pass the light transmission of intraocular lens until maximum possible.Compare with short wavelength's compound-violet, this part of blue spectrum is less to amphiblestroid infringement, and higher transmission is fine.The scope of the preferred characteristics in high transmit blue district is also listed in the table 1.
Table 1 transmissison characteristic
Figure G200780038094XD00031
The accompanying drawing summary
Fig. 1 and Fig. 2 have shown the absorbance of the ocular devices material of embodiment 1 and 2.
Detailed Description Of The Invention
Except as otherwise noted, all components amount is all shown based on % (w/w) (" % by weight ") Show.
Wavelength when unless otherwise, " cut-off " refers to that the light transmission is no more than 1%. " 1% cut-off " Refer to the wavelength when the light transmission is no more than 1%. " 10% cut-off " is when referring to that the light transmission is no more than 10% Wavelength.
According to the concentration of UV absorbent, typical BTA or benzophenone UV absorbent for The IOL material all provides precipitous cut-off at the wavelength less than 400 nanometers. But, some replacement 2-hydroxy phenyl benzotriazole UV absorbers is in visible (410-430 nanometer) zone of the short wavelength of spectrum The transmission cut-off can be provided, and the protection for UV radiation (＜400 nanometer) is provided. Be suitable for Represented by formula (I) in the UV/ of ocular devices material of the present invention short-wavelength visible light absorbent.
Figure G200780038094XD00041
Wherein for formula (I)
R 1Halogen, OH, C1-C 12Alkoxyl, optionally substituted phenoxy group or substituted naphthoxy optionally, wherein said non-essential substituting group is C1-C 6Alkyl, C1-C 6Alkoxyl, OH ,-(CH2CH 2O) n-or-(CH2CH(CH 3)O) n-；
R 2Be C 1-C 12Alkyl, (CH 2CH 2O) n, (CH 2CH (CH 3) O) n, or CH 2CH 2CH 2(Si (CH 3) 2O) mSi (CH 3) 2CH 2CH 2CH 2
If R 2Be (CH 2CH 2O) nOr (CH 2CH (CH 3) O) n, then X does not exist, otherwise X is O, NR 4Or S;
R 3Do not exist or C (=O), C (=O) C jH 2j, C 1-C 6Alkyl, phenyl or C 1-C 6Alkyl phenyl;
R 4Be H or methyl;
R 5Be H, C 1-C 6Alkyl or phenyl;
R 6Be H or C 1-C 12Alkyl;
N is 2-10; With
J is 1-6.
Preferably, in formula (I),
R 1Be Cl, Br, C 1-C 4Alkoxyl or phenoxy group;
R 2Be C 1-C 6Alkyl;
X is O or NR 4
R 3Be C (=O) or C 1-C 6Alkyl phenyl;
R 4Be H or methyl;
R 5Be H; With
R 6Be C 4-C 12Tertiary alkyl.
Most preferably, in formula (I),
R 1It is methoxyl group;
R 2Be C 2-C 3Alkyl;
X is O;
R 3Be C (=O);
R 4Be H or methyl;
R 5Be H; With
R 6It is the tert-butyl group.
Formula (I) chemical compound can prepare with method as known in the art.Two kinds of preferred formulas (I) chemical compound be 2-{2 '-hydroxyl-3 '-tert-butyl group-5 ' [3 " (4 " '-vinyl benzyloxy base) propoxyl group] phenyl-5-methoxyl group-2H-benzotriazole:
Figure G200780038094XD00051
And 2-[2 '-hydroxyl-3 '-tert-butyl group-5 '-(3 " the methacryloxy propoxyl group) phenyl]-5-methoxyl group-2H-benzotriazole:
Figure G200780038094XD00052
Device material of the present invention comprises and weakens medium wavelength to the polymerizable weld of long wavelength (430-500nm) blue light.Many such welds are known, and comprise the dyestuff that for example has following structure:
Figure G200780038094XD00061
And describe in the United States Patent (USP) 7,098,283,6,878,792,6,320,008 and 6,310,215 those.Be applicable to that preferred polymerizable weld in the device material of the present invention is those shown in the formula (II):
Wherein for formula (II),
R ' and R " are H or CH independently 3
R 6And R 7Be H, C independently 1-C 20Alkyl, OCH 3, OC 2H 5, OC 3H 7Or OC 4H 9
I and j are 1 or 2 independently;
R 8, R 9, R 10And R 11Independently for have maximum 10 atoms, by carbon, hydrogen, silicon, oxygen, nitrogen, phosphorus, sulfur, chlorine, bromine or fluorine separately or the non-ring type organic spacer group that constitutes of combination in any;
K and m are 1 to 6 independently;
L and n are 0 to 6 independently;
X is O, NH, NR 5With
R 5=C 1-C 10Alkyl.
Most preferred formula (II) chemical compound is N, N-pair-(2-methacryloxyethyl)-(4-phenylazo) aniline:
Figure G200780038094XD00071
The polymerizable weld shown in the formula (III) more preferably:
Figure G200780038094XD00072
Wherein for formula (III),
R is H or CH 3
R 1Be H, C 1-C 10Alkyl, OCH 3, OC 2H 5, OC 3H 7, or OC 4H 9
A and b are 1 or 2 independently;
R 2Be R 1, OH, NH 2, NHR 5, N (R 5) 2, SH, SR 5, OR 5, OSi (R 5) 3Or Si (R 5) 3
R 3Be directly connected on the dyestuff residue, and constitute by alkyl with maximum 6 carbon atoms;
R 4Be have maximum 10 atoms, by carbon, hydrogen, silicon, oxygen, nitrogen, phosphorus, sulfur, chlorine, bromine or fluorine separately or the non-ring type organic spacer group that constitutes of combination in any;
X is O, NH, NR 5
R 5Be C 1-C 10Alkyl;
D, e, g and h are 0 to 4 integer independently; With
C and f are 1 to 4 integer independently.
Most preferred formula (III) chemical compound is N-2-[3-(2 '-methylbenzene azo group)-4-hydroxy phenyl] the ethyl-methyl acrylamide:
Figure G200780038094XD00081
Formula (II) and (III) shown in the polymerizable weld be known, and be described in United States Patent (USP) 5,470, in 932, the whole contents of this patent merges to herein by reference.
Ocular devices material of the present invention comprises UV absorbent shown in a certain amount of formula (I) and a certain amount of polymerizable weld, so that this material has above-mentioned desired transmissison characteristic.This material is generally with 0.5-4%, preferred 1-3%, most preferably the amount of 1.5-2.5% comprises the UV/ short-wavelength visible light absorbent shown in the formula (I).This material is usually with 0.001-0.5%, preferred 0.01-0.1%, most preferably the amount of 0.01-0.05% comprises polymerisable weld.
The monomer of many formation devices is as known in the art, and comprises acrylic monomer and the monomer that contains siloxanes.As seen, for example, United States Patent (USP) 7,101,949,7,067,602,7,037,954,6,872,793,6,852,793,6,846,897,6,806,337,6,528,602 and 5,693,095.Under the situation that is IOL, any known IOL material all is applicable to compositions of the present invention.More preferably, the monomer of described formation device comprises the monomer shown in the formula (IV):
Figure G200780038094XD00082
Wherein:
A is H, CH 3, CH 2CH 3Or CH 2OH;
B is (CH 2) mOr [O (CH 2) 2] z
C is (CH 2) w
M is 2-6;
Z is 1-10;
Y does not exist or O, S or NR ', and condition is that then B is (CH if Y is O, S or NR ' 2) m
R ' is H, CH 3, C N 'H 2n '+1(n '=1-10), different-OC 3H 7, C 6H 5Or CH 2C 6H 5
W is 0-6, and condition is m+w≤8; With
D is H, C 1-C 4Alkyl, C 1-C 4Alkoxyl, C 6H 5, CH 2C 6H 5Or halogen.
Preferred formula (IV) monomer is that wherein A is H or CH 3, B is (CH 2) m, m is that 2-5, Y do not exist or O, w are that 0-1 and D are those of H.Most preferably methacrylic acid 2-phenylethylester, methacrylic acid 4-phenyl butyl ester, methacrylic acid 5-phenylpentyl ester, methacrylic acid 2-benzyloxy ethyl ester, methacrylic acid 3-benzyloxy propyl diester and their corresponding acrylate.
Formula (IV) monomer is known, and the preparation of available known method.For example, can in reaction vessel, required monomeric conjugated alcohol and methyl methacrylate, butyl titanate (catalyst) and polymerization be pressed down formulation (for example 4-benzyloxy phenol) merging.Then with the heating of this reaction vessel, make and react completely to promote reaction and to distill out byproduct of reaction.Other synthetic schemes relates to and methacrylic acid is added in the conjugated alcohol and uses carbodiimide catalyzed, or conjugated alcohol is mixed with methacrylic chloride and alkali (for example pyridine or triethylamine).
Material of the present invention comprises altogether the monomer of at least 75%, preferred at least 80% formation device usually.
Except the UV absorbent and polymerizable weld of the monomer that forms device, formula (I), material of the present invention also comprises cross-linking agent.The cross-linking agent that is used for device material of the present invention can be any terminal alkene formula unsaturated compound with the unsaturated group that surpasses.Suitable crosslinking agent for example comprises: ethylene glycol dimethacrylate; Diethylene glycol dimethacrylate; Allyl methacrylate; 1, the ammediol dimethylacrylate; 2, the ammediol dimethylacrylate; 1, the 6-hexanediol dimethacrylate; 1, the 4-butanediol dimethylacrylate; CH 2=C (CH 3) C (=O) O-(CH 2CH 2O) pC (=O) C (CH 3)=CH 2, p=1-50 wherein; And CH 2=C (CH 3) C (=O) O (CH 2) tO-C (=O) C (CH 3)=CH 2, T=3-20 wherein; And their corresponding acrylate.Preferred cross-linking monomer is CH 2=C (CH 3) C (=O) O-(CH 2CH 2O) pC (=O) C (CH 3)=CH 2, wherein p makes that its number-average molecular weight is about 400, about 600 or about 1000.
Usually, the total amount of cross-linking agent composition is at least 0.1 weight %, and according to classification and the concentration and the required physical characteristic of all the other components, can reach about 20 weight %.The preferred cross-linking agents component concentration ranges is 0.1-17% (w/w).
The suitable polymerization initiators of device material of the present invention comprises thermal initiator and light trigger.Preferred thermal initiator comprises the peroxy radical initiator, for example (peroxide-2-ethyl) caproic acid tertiary butyl ester and peroxide two carbonic acid two-(tert-butylcyclohexyl) ester (can
Figure G200780038094XD00101
16 available from Akzo ChemicalsInc., Chicago, Illinois).Initiator exists with 5% (w/w) or amount still less usually.Because radical initiator can be in a part that chemically becomes formed polymer, therefore when determining the amount of other composition, in the amount of initiator is not included in usually.
Preferably, select each component and ratio thereof, so that device material of the present invention has following characteristic: make material of the present invention be specially adapted to the IOL that will insert by 4 millimeters or otch still less.For the purpose of convenient, this device material can be described as lens material.
Measure in 589 nanometers (sodium lamp) by abbe's refractometer, lens material preferably has the dry state refractive index at least about 1.50.For given optical diameter, being lower than optics that 1.50 material makes by refractive index must be thicker than the optics of the identical performance of being made by the material of high index of refraction more.Therefore, being lower than the IOL optics that about 1.50 material makes by refractive index generally needs bigger IOL to implant otch.
The glass transition temperature of described lens material (" Tg ", it has influence on the folding of material and launches performance) preferably is lower than about 25 ℃, more preferably less than about 15 ℃.Tg in 10 ℃ of/minute mensuration, and is defined as the half-peak height that thermal capacitance increases by differential scanning calorimetry.
Described lens material has at least 75%, preferred at least 90%, most preferably at least 100% percentage elongation (breaking strain).This character shows that lens generally do not break, tear or ftracture when folding.The percentage elongation of polymer samples is determined by dumb-bell shape extension test sample, 20 millimeters of this sample total lengths, 11 millimeters of clamping director degree, 2.49 millimeters of overall widths, 0.833 millimeter of the width of narrow portion, 8.83 millimeters of chamfer radius, 0.9 millimeter of thickness.Under the standard laboratory conditions of 23 ± 2 ℃ and 50 ± 5% relative humiditys, use the pull test instrument that sample is tested.The clamping spacing is made as 11 millimeters, and crosshead speed is made as 500 mm/min, and the tractive sample is to damaging.Displacement when breaking strain is recorded as damage is with respect to the mark of initial clamping spacing.Fracture strength is to calculate under the maximum load of sample, the normally load during sample breakage (the supposition prime area keeps constant).Young's modulus is calculated by the instant slope of the load-deformation curve in linear elasticity district.25% secant modulus is calculated as the collinear slope that draws on the load-deformation curve between 0% strain and 25% strain.100% secant modulus is calculated as the collinear slope that draws on the load-deformation curve between 0% strain and 100% strain.
By the IOL of material of the present invention structure can be any design that can be curled or be folded into little cross section, can lay by less otch.For example, this IOL can be so-called monolithic or multi-disc design, comprises optics and sense of touch part.Opticator is the part as lens.Sense of touch part links to each other with opticator, and opticator is remained on tram in the eye.Optics and sense of touch part can be made by identical or different material.The multi-disc lens gain the name be because optics and sense of touch partly be separately make and then sense of touch partly be connected on the opticator.In single element lens, optics and sense of touch part are formed by one piece material.According to material, from this material, cut or cut the sense of touch part then to make IOL.
Except IOL, material of the present invention also is applicable to and uses other ocular devices, for example contact lens, artificial cornea and corneal ring or corneal inlay.
Further explain the present invention by following embodiment, these embodiment are used for explaining and unrestricted the present invention.
Embodiment 1: comprise 2-[2 '-hydroxyl-3 '-tert-butyl group-5 '-(3 " methacryloxy propoxyl group) phenyl]-5-methoxyl group-2H-benzotriazole (" UV13 ") and N-2-[3-(2 '-methylbenzene azo group)-4-hydroxy phenyl] acrylic device of ethyl-methyl acrylamide (" AL8739 ")
With acrylic acid 2-phenylethylester (PEA), methacrylic acid 2-phenylethylester (PEMA) and 1,4-butanediol diacrylate (BDDA) prepares the 60 gram monomers dilution formulations of being made up of these three kinds of monomers with the mixed of 65: 30: 3.2 weight portions together thus.0.5 gram UV13 is dissolved in the 19.5 gram PEA/PEMA/BDDA formulations, with preparation 2.5%UV raw sorbent formulation.At last, 0.25 gram AL8739 is dissolved in the 9.75 gram PEA/PEMA/BDDA formulations, comprises the second preparation of raw material thing of 0.25%AL8739 with preparation.
By with the ratio shown in the table 2 two kinds of preparation of raw material things being mixed with PEA/PEMA/BDDA dilution formulation, preparation comprises 0.2 to 2% UV13 and the AL8739 of 0.01-0.04% and 17 kinds of PEA/PEMA/BDDA formulations of a control sample that does not contain AL8739 (17).
The preparation scheme of the PEA/PEMA formulation of table 2 UV13 and AL8739
Figure G200780038094XD00131
Use Perkin-Elmer Lambda 35 instruments, by UV-visible light transmission spectrographic method, analyze each formulation in the quartz cell of 1 millimeter optical path length, this provides reasonable related with the IOL central thickness.After carrying out background correction with the PEA/PEMA/BDDA formulation, from 300 to 800 nanometers are analyzed each 16 kinds of formulations.The gained transmitted spectrum as shown in Figure 1.
In each formulation, add 0.5% pair-(4-tert-butylcyclohexyl peroxide) two carbonic esters (Perkadox-16, Akzo Corp.) initiator, mix its dissolving by eddy current.After the mixing, make the membrane filter of each formulation, and purge with nitrogen by 0.2 μ m.At last, each formulation is dropped in polypropylene mould, by in the programmable stove of temperature 80 ℃ solidify 1 hour, solidified 1 hour and solidify the rectangular membrane (" plate ") that formed 1 * 2 cm x～1 millimeter in 1 hour at 90 ℃ at 100 ℃.
After curing, with the film demoulding, putting into, the polypropylene fabric capsule of labelling is used for further processing.With acetone membrane sample is carried out Soxhlet and extracts, at air drying, and 60 ℃ in a vacuum dry (＜0.1 inch of mercury) to remove residual acetone.
Embodiment 2: have the 2%UV13 of different content AL8739 chromophore and the comparative example of 2%oMTP
This embodiment provides conventional benzotriazole UV absorbers oMTP (neighbour-methylallyl Tinuvin P) and the comparison that is used for the UV/ short-wavelength visible light absorbent of material of the present invention.0.250 gram oMTP is dissolved in 9.752 gram embodiment, the 1 described PEA/PEMA/BDDA monomer diluent, prepare another raw material 2.56%oMTP solution.When preparation as described below contrasts formulation, also use the preparation of raw material thing solution that contains 0.25%AL8739 polymerizable weld.
By according to the scheme that provides in the table 3 in conjunction with preparation of raw material thing solution, prepare 5 kinds and contain 2%oMTP and 0,0.01,0.02,0.03 and the oMTP formulation of 0.04%AL8739 polymerizable weld.
Table 3 contains the preparation scheme of the PEA/PEMA formulation of oMTP and AL8739 blue light chromophore
Figure G200780038094XD00151
In each formulation, add 0.5% pair-(4-tert-butylcyclohexyl peroxide) two carbonic esters (Perkadox-16, Akzo Corp.) initiator, mix making its dissolving by eddy current.After the mixing, make the membrane filter of each formulation, and purge with nitrogen by 0.2 μ m.At last, each formulation is dropped in polypropylene mould, by in the programmable stove of temperature 80 ℃ solidify 1 hour, solidified 1 hour and solidify the rectangular membrane that formed 1 * 2 cm x～1 millimeter in 1 hour at 90 ℃ at 100 ℃.
After curing, with the film demoulding, putting into, the polypropylene fabric capsule of labelling is used for further processing.With acetone membrane sample is carried out Soxhlet and extracts, at air drying, and 60 ℃ in a vacuum dry (＜0.1 inch of mercury) to remove residual acetone.Behind extraction and the vacuum drying, use Perkin-Elmer Lambda 35 instruments that are equipped with LabSphere RSA-PE-20 integrating sphere, by UV-visible light transmission spectrographic method, from 300-800 nanometer analyzing film sample.Similarly, also use UV-visible light transmission analysis of spectral method from the film 1-4 of embodiment 1 and 17 plates to make comparisons.
The result as shown in Figure 2, this figure provide embodiment 1 formulation 1-4,17 and the spectrum of the 1-5 of embodiment 2 relatively.Table 4 provide from Fig. 2 transmission data for 1% and the wavelength that ends of 10%UV.Clearly, compare with the UV/ short-wavelength visible light absorbent (for example UV13) of formula (I), conventional benzotriazole UV absorbers, oMTP for example, (410-430 nanometer) do not provide significantly and ends in the short-wavelength visible light district.Totally weakening by adding AL8739 polymerizable weld of the blue light of 400-500 nanometer is maintained, and the %T value representation by providing in 450 nanometers.
For all embodiment 1 (UV13 and AL8739) formulation 1-4,1% terminates in that between the 421-423 nanometer, 10% terminates in the scope of 426.5 to 432 nanometers.Different therewith, in embodiment 2 (oMTP and AL8739) formulation 1-4,1% of formulation 1-4 terminates in the scope of 396.5 to 399 nanometers, and 10% terminates in the scope of 401.5 to 413 nanometers.This contrast shows, by UV13 formulation (embodiment 1), has realized improved the ending with respect to oMTP formulation (embodiment 2) at short-wavelength visible light zone (410-430).450 nanometer transmissions are indications that blue light weakens, and for variant AL8739 concentration, the difference between UV13 and the oMTP formulation is about 6%T.
The comparison of the UV-visible data of table 4 embodiment 1 and 2 formulations
Figure G200780038094XD00171
By some the present invention has been described preferred embodiment; But should be appreciated that the present invention can also be embodied in other concrete form or change in and do not deviate from its special or basic feature.Therefore, will be understood that above-mentioned embodiment all is illustrative rather than restrictive in all respects, protection scope of the present invention is to define by appended claim rather than by top description.

Claims (19)

1. ocular devices material comprises:
A) the UV/ short-wavelength visible light absorbent of formula (I):
Figure A2007800380940002C1
Wherein for formula (I)
R 1Be halogen, OH, C 1-C 12Alkoxyl, optionally substituted phenoxy group or optionally substituted naphthoxy, wherein said non-essential substituent group is C 1-C 6Alkyl, C 1-C 6Alkoxyl, OH ,-(CH 2CH 2O) n-or-(CH 2CH (CH 3) O) n-;
R 2Be C 1-C 12Alkyl, (CH 2CH 2O) n, (CH 2CH (CH 3) O) n, or CH 2CH 2CH 2(Si (CH 3) 2O) mSi (CH 3) 2CH 2CH 2CH 2
If R 2Be (CH 2CH 2O) nOr (CH 2CH (CH 3) O) n, then X does not exist, otherwise X is O, NR 4Or S;
R 3Do not exist or C (=O), C (=O) C jH 2j, C 1-C 6Alkyl, phenyl or C 1-C 6Alkyl phenyl;
R 4Be H or methyl;
R 5Be H, C 1-C 6Alkyl or phenyl;
R 6Be H or C 1-C 12Alkyl;
N is 2-10; With
J is 1-6;
B) weaken the polymerizable weld of the light of wavelength in the 430-500 nanometer range;
C) monomer of formation device, its amount is 75 weight % or more; With
D) cross-linking agent,
The amount of wherein said UV/ short-wavelength visible light absorbent and the amount of described polymerizable weld are enough to make described ocular devices material to have following optical transmission characteristics:
Figure A2007800380940003C1
2. ocular devices material as claimed in claim 1, wherein in formula (I),
R 1Be Cl, Br, C 1-C 4Alkoxyl or phenoxy group;
R 2Be C 1-C 6Alkyl;
X is O or NR 4
R 3Be C (=O) or C 1-C 6Alkyl phenyl;
R 4Be H or methyl;
R 5Be H; With
R 6Be C 4-C 12Tertiary alkyl.
3. ocular devices material as claimed in claim 2, wherein in formula (I),
R 1It is methoxyl group;
R 2Be C 2-C 3Alkyl;
X is O;
R 3Be C (=O);
R 4Be H or methyl;
R 5Be H; With
R 6It is the tert-butyl group.
4. ocular devices material as claimed in claim 1, wherein said UV/ short-wavelength visible light absorbent formula (I) be selected from by 2-{2 '-hydroxyl-3 '-tert-butyl group-5 ' [3 " (4 " '-vinyl benzyloxy base) propoxyl group] phenyl-5-methoxyl group-2H-benzotriazole and 2-[2 '-hydroxyl-3 '-tert-butyl group-5 '-(3 " methacryloxy propoxyl group) phenyl]-group that the 5-methoxyl group-the 2H-benzotriazole is formed.
5. ocular devices material as claimed in claim 1, wherein said polymerizable weld select free style (II) dyestuff, formula (III) dyestuff and
Figure A2007800380940004C1
The group of forming;
Wherein for formula (II),
R ' and R " are H or CH independently 3
R 6And R 7Be H, C independently 1-C 20Alkyl, OCH 3, OC 2H 5, OC 3H 7Or OC 4H 9
I and j are 1 or 2 independently;
R 8, R 9, R 10And R 11Independently for have maximum 10 atoms, by carbon, hydrogen, silicon, oxygen, nitrogen, phosphorus, sulfur, chlorine, bromine or fluorine separately or the non-ring type machine spacer groups that constitutes of combination in any;
K and m are 1 to 6 independently;
L and n are 0 to 6 independently;
X is O, NH, NR 5With
R 5=C 1-C 10Alkyl;
Figure A2007800380940005C1
Wherein for formula (III),
R is H or CH 3
R 1Be H, C 1-C 10Alkyl, OCH 3, OC 2H 5, OC 3H 7, or OC 4H 9
A and b are 1 or 2 independently;
R 2Be R 1, OH, NH 2, NHR 5, N (R 5) 2, SH, SR 5, OR 5, OSi (R 5) 3Or Si (R 5) 3
R 3Be directly connected on the dyestuff residue, and constitute by alkyl with maximum 6 carbon atoms;
R 4Be have maximum 10 atoms, by carbon, hydrogen, silicon, oxygen, nitrogen, phosphorus, sulfur, chlorine, bromine or fluorine separately or the non-ring type organic spacer group that constitutes of combination in any;
X is O, NH, NR 5
R 5Be C 1-C 10Alkyl;
D, e, g and h are 0 to 4 integer independently; With
C and f are 1 to 4 integer independently.
6. ocular devices material as claimed in claim 5, wherein said polymerizable weld is selected from by N, and N-is two-(2-methacryloxyethyl)-(4-phenylazo) aniline and N-2-[3-(2 '-methylbenzene azo group)-4-hydroxy phenyl] group formed of ethyl-methyl acrylamide.
7. ocular devices material as claimed in claim 1, the amount of wherein said UV/ short-wavelength visible light absorbent are 0.5-4 weight %.
8. ocular devices material as claimed in claim 7, the amount of wherein said UV/ short-wavelength visible light absorbent are 1-3 weight %.
9. ocular devices material as claimed in claim 7, the amount of wherein said UV/ short-wavelength visible light absorbent are 1.5-2.5 weight %.
10. ocular devices material as claimed in claim 1, the amount of wherein said polymerizable weld are 0.001-0.5 weight %.
11. ocular devices material as claimed in claim 10, the amount of wherein said polymerizable weld are 0.01-0.1 weight %.
12. ocular devices material as claimed in claim 10, the amount of wherein said polymerizable weld are 0.01-0.05 weight %.
13. ocular devices material as claimed in claim 1, the monomer of wherein said formation device are selected from by acrylic monomer or contain the group that the monomer of siloxanes is formed.
14. ocular devices material as claimed in claim 13, the monomer of wherein said formation device are the monomers of formula (IV):
Figure A2007800380940007C1
Wherein for formula (IV):
A is H, CH 3, CH 2CH 3Or CH 2OH;
B is (CH 2) mOr [O (CH 2) 2] z
C is (CH 2) w
M is 2-6;
Z is 1-10;
Y does not exist or O, S or NR ', and condition is that then B is (CH if Y is O, S or NR ' 2) m
R ' is H, CH 3, C N 'H 2n '+1(n '=1-10), different-OC 3H 7, C 6H 5Or CH 2C 6H 5
W is 0-6, and condition is m+w≤8; With
D is H, C 1-C 4Alkyl, C 1-C 4Alkoxyl, C 6H 5, CH 2C 6H 5Or halogen.
15. ocular devices material as claimed in claim 14, wherein for formula (IV), A is H or CH 3, B is (CH 2) m, m is 2-5, and Y does not exist or O, and w is 0-1, and D is H.
16. ocular devices material as claimed in claim 15, the monomer of wherein said formation device are selected from the group of being made up of methacrylic acid 2-phenylethylester, methacrylic acid 4-phenyl butyl ester, methacrylic acid 5-phenylpentyl ester, methacrylic acid 2-benzyloxy ethyl ester, methacrylic acid 3-benzyloxy propyl diester and their corresponding acrylate.
17. ocular devices material as claimed in claim 1, wherein said cross-linking agent is selected from by ethylene glycol dimethacrylate; Diethylene glycol dimethacrylate; Allyl methacrylate; 1, the ammediol dimethylacrylate; 2, the ammediol dimethylacrylate; 1, the 6-hexanediol dimethacrylate; 1, the 4-butanediol dimethylacrylate; CH 2=C (CH 3) C (=O) O-(CH 2CH 2O) pC (=O) C (CH 3)=CH 2, p=1-50 wherein; And CH 2=C (CH 3) C (=O) O (CH 2) tO-C (=O) C (CH 3)=CH 2, T=3-20 wherein; And the group of their corresponding acrylate compositions.
18. ocular devices material as claimed in claim 1, the amount of wherein said cross-linking agent are 0.1-20 weight %.
19. ocular devices material as claimed in claim 1, wherein this ocular devices is selected from by intraocular lens, contact lens, artificial cornea, or the group of corneal ring or corneal inlay composition.
CN200780038094A 2006-10-13 2007-10-12 Have unique indigo plant-purple by with the intraocular lens of blue light transmissison characteristic Pending CN101663053A (en)

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104395387A (en) * 2012-06-26 2015-03-04 诺华股份有限公司 2-amino benzophenone UV-absorbers for ophthalmic lens materials
CN104693646A (en) * 2015-03-16 2015-06-10 南京工业大学 Transparent plasticized PVC (Polyvinyl Chloride) functional film and preparation method
CN106773319A (en) * 2017-01-24 2017-05-31 深圳市华星光电技术有限公司 Display device and preparation method thereof
CN108603946A (en) * 2016-02-08 2018-09-28 依视路国际公司 Including the blue light of benzotriazole UV absorbers blocks optical material
CN109716217A (en) * 2016-09-20 2019-05-03 依视路国际公司 The optical goods of blue light cut-off, high UV cut-off and the high grade of transparency

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104395387A (en) * 2012-06-26 2015-03-04 诺华股份有限公司 2-amino benzophenone UV-absorbers for ophthalmic lens materials
CN104693646A (en) * 2015-03-16 2015-06-10 南京工业大学 Transparent plasticized PVC (Polyvinyl Chloride) functional film and preparation method
CN108603946A (en) * 2016-02-08 2018-09-28 依视路国际公司 Including the blue light of benzotriazole UV absorbers blocks optical material
CN108603946B (en) * 2016-02-08 2021-07-27 依视路国际公司 Blue light blocking optical materials comprising benzotriazole UV absorbers
CN109716217A (en) * 2016-09-20 2019-05-03 依视路国际公司 The optical goods of blue light cut-off, high UV cut-off and the high grade of transparency
CN106773319A (en) * 2017-01-24 2017-05-31 深圳市华星光电技术有限公司 Display device and preparation method thereof

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