CN1970640B - Ocular colorant and colorful ocular material using same - Google Patents
Ocular colorant and colorful ocular material using same Download PDFInfo
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- CN1970640B CN1970640B CN2005101248626A CN200510124862A CN1970640B CN 1970640 B CN1970640 B CN 1970640B CN 2005101248626 A CN2005101248626 A CN 2005101248626A CN 200510124862 A CN200510124862 A CN 200510124862A CN 1970640 B CN1970640 B CN 1970640B
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Abstract
The invention discloses an eyepiece colorant as formula I or formula II.
Description
Technical field
The present invention relates to as contact lens and ophthalmic lens eyepiece (ocularlense) tinting materials such as (intraocular lenses), and the coloured eyepiece material that uses this tinting material.
Background technology
Known coloured ophthalmic lens, in this ophthalmic lens, regulate about 400nm extremely the light transmissivity of the blue region of about 500nm to slow down retina photodamaged (retinal light damage) or as the counter measure of cyanopsia.In these coloured ophthalmic lenss, by yellow colorants, red stain, orange colorant etc. being mediated to as in the hard intraocular lens material such as PMMA, ophthalmic lens can be coloured to yellow, redness, orange etc. with material.A kind of invention for the treatment of the soft ophthalmic lens of cyanopsia is also proposed, the following acquisition of described soft ophthalmic lens: a small amount of tinting material is added in the flexible and soft intraocular lens material, with obtain colored soft ophthalmic lens (referring to, JP-A-7-24052).
Owing to have a dense molecular structure, stand to mediate the wash-out (bleeding) of the tinting material in it hardly as hard intraocular lens material such as PMMA.Yet when tinting material is added into the soft intraocular lens material that is ready to use in soft ophthalmic lens, the problem that occurs is: because the reason of the coarse particales structure (coarse molecular structure) of soft intraocular lens material, tinting material will come out by wash-out from soft intraocular lens material.
Summary of the invention
Technical problem to be solved by this invention provides the eyepiece that can use and not have a wash-out problem with tinting material and coloured eyepiece material of using this tinting material, has realized the present invention for solving these problems that occur in the prior art.
The present inventor finds that the compound that following general formula I and II represent is suitable as for example eyepiece such as contact lens and ophthalmic lens tinting material,
(in formula I and II, Y represents H or CH
3N is the integer of 1-5).In the compound that general formula I is represented, Y is CH
3With n be that 1 compound can be especially suitable for use as the eyepiece tinting material.In the compound that general formula I I represents, Y is CH
3With n be that 2 compound can be especially suitable for use as the eyepiece tinting material.
And, coloured eyepiece contains 0.003 weight % or more but be no more than eyepiece that the general formula I of 0.03 weight % represents with tinting material and 0.0003 weight % or more but be no more than the eyepiece tinting material that the general formula I I of 0.003 weight % represents with material, the content of each tinting material is all based on gross weight, control the optical transmission of about 400nm to 500nm blue region, show light transmission character thus near human lens (humanlens).
Tinting material of the present invention can be advantageously utilised in the eyepiece, for example in soft contact lens and the ophthalmic lens, and after wearing not from eyepiece wash-out come out.
Description of drawings
The ophthalmic lens that Fig. 1 is to use tinting material of the present invention the to obtain figure of the transmissivity of body material.
Embodiment
Below, the mode of the present invention of implementing will be described.
＜preparation eyepiece tinting material 〉
The method of the synthetic compound of representing with the general formula I of tinting material as eyepiece of the present invention of specific implementation at first, is described.The compound that general formula I is represented can be coloured to yellow with coloured eyepiece.In addition, this compound advantageously with eyepiece with material (monomer) copolymerization, therefore hardly from eyepiece wash-out come out.Can prepare the compound that general formula I is represented according to for example following reaction formula.
More specifically, the compound (wherein n is the integer of 1-5) that supply general formula III and IV represent under acidic conditions, the stirring and refluxing scheduled time under preset temperature.Then, add the solvent of predetermined amount, for example pure (for example, methyl alcohol) or ether, the mixture of reaction gained obtains the compound that general formula V represents when the preset temperature continuously stirring.
Next, the compound that general formula V is represented is added in the anhydrous methylene chloride.(wherein Y is H or CH to the compound that the above-mentioned general formula VI of interpolation represents in it
3) and 4-Dimethylamino pyridine, and the mixture of gained stirred the scheduled time.In time limit, in the solution that obtains, add N-ethyl-N '-(3-dimethylamino-propyl) carbodiimide hydrogen chlorate at preset time, and the mixture scheduled time of stirring reaction gained.Therefore, can obtain the required compound that general formula I is represented, it can be used as the eyepiece tinting material.
Next, the method for the synthetic compound of representing with the general formula I I of tinting material as eyepiece of the present invention of specific implementation is described.The compound that general formula I I represents can be coloured to redness with coloured eyepiece.In addition, this compound advantageously with eyepiece with material (monomer) copolymerization, therefore hardly from eyepiece wash-out come out.Can prepare the compound that general formula I I represents according to following reaction formula.
More specifically, the compound that general formula X I is represented (wherein n is the integer of 1-5) is added in the anhydrous methylene chloride.(wherein Y is H or CH to the compound that the above-mentioned general formula VI of interpolation represents in it
3) and 4-Dimethylamino pyridine, and the mixture of gained stirred the scheduled time.In time limit, in the solution that obtains, add N-ethyl-N '-(3-dimethylamino-propyl) carbodiimide hydrogen chlorate at preset time, and the mixture scheduled time of stirring reaction gained.Therefore, can obtain the required compound that general formula I I represents, it can be used as the eyepiece tinting material.
Can prepare the compound that general formula X I represents according to following reaction formula.
More specifically, sodium bisulfite is dissolved in the water, and it inwardly adds formlinata aquae concentratac.After the stirring, in it, add the compound (wherein n is the integer of 1-5) that general formula VII represents, and the mixture of stirring reaction gained in the given time, thereby solution A obtained.Independently, concentrated hydrochloric acid is dissolved in the water, and in it, adds the compound (aniline) that general formula VIII represents, then cooling.In time limit, in this solution, dropwise add sodium nitrite in aqueous solution at the fixed time, the mixture of stirring reaction gained at low temperatures, thus obtain solution B.Be added in the above-mentioned solution A the solution B of gained is disposable, and under preset temperature mixture scheduled time of reaction gained.In addition, aqueous sodium hydroxide solution is added in the above-mentioned solution, and the mixture of reaction gained.Then, be settled out reaction product, and the purifying throw out that obtains like this, thereby the compound that general formula I X represents obtained.
The compound that the general formula I X that so obtains is represented is added in the hydrochloric acid, and with ice-cooled.In the solution that obtains, dropwise add sodium nitrite in aqueous solution, stir the mixture scheduled time of gained.Be added in the sodium hydroxide solution the solution of gained is disposable, described sodium hydroxide solution contains the dissolving compound of being represented by general formula X (2-Naphthol) within it, reaction then, thus obtain the compound that general formula X I represents.
＜prepare coloured ophthalmic lens 〉
Next, illustrate that the eyepiece that utilizes above-mentioned general formula I and II to represent prepares the method for coloured ophthalmic lens with tinting material.
As for the intraocular lens material of using in this embodiment, can use conventional those that use.Specially suitable is that using is soft and flexible intraocular lens material when room temperature.The example of this softish intraocular lens material comprises straight chain, side chain and ring-type (methyl) alkyl acrylate, for example (methyl) methyl acrylate, (methyl) ethyl propenoate, (methyl) propyl acrylate, (methyl) n-butyl acrylate, (methyl) tert-butyl acrylate, (methyl) isobutyl acrylate, (methyl) vinylformic acid n-pentyl ester, (methyl) vinylformic acid tert-pentyl ester, (methyl) Ethyl acrylate, (methyl) vinylformic acid 2-methyl butyl ester, (methyl) vinylformic acid heptyl ester, (methyl) Octyl acrylate, (methyl) 2-EHA, (methyl) vinylformic acid ester in the ninth of the ten Heavenly Stems, (methyl) decyl acrylate, (methyl) dodecylacrylate, (methyl) vinylformic acid stearyl, (methyl) vinylformic acid ring pentyl ester, (methyl) cyclohexyl acrylate and ethylene glycol amyl ether acrylate.Use in them one or more and the multipolymer that obtains can be used as soft propylene acids body material.Term used herein " (methyl) vinylformic acid--ester " expression " vinylformic acid--ester " or " methacrylic acid---ester ".
In purpose is to obtain can to use following substances under the situation of soft ophthalmic lens on possess hydrophilic property surface, and for example, the N-vinyl lactam is as N-vinyl pyrrolidone, alpha-methylene-N-Methyl pyrrolidone and N-caprolactam; (methyl) acrylate of hydroxyl is as (methyl) Hydroxyethyl acrylate, (methyl) Propylene glycol monoacrylate, (methyl) vinylformic acid hydroxy butyl ester, (methyl) vinylformic acid dihydroxyl propyl ester, (methyl) vinylformic acid dihydroxyl dibutylester, diglycol monotertiary (methyl) acrylate, triglycol list (methyl) acrylate and dipropylene glycol list (methyl) acrylate; (methyl) vinylformic acid; (methyl) acrylamide, N-methyl (methyl) acrylamide, N-ethyl (methyl) acrylamide, N-hydroxyethyl (methyl) acrylamide, N, N-dimethyl (methyl) acrylamide, N, N-diethyl (methyl) acrylamide, N-ethylamino ethyl (methyl) acrylamide etc.
Can also use their multipolymer, for example, the multipolymer of the multipolymer of Jia Jibingxisuanyizhi and methyl methacrylate, methacrylic acid 2-ethylhexyl and butyl methacrylate and the combinations such as multipolymer of methacrylic acid 2-ethylhexyl and lauryl methacrylate.
For utilizing above-mentioned eyepiece material preparation colour soft body material (or its material), can be with above-mentioned (methyl) acrylate and various vinyl-based copolymerisable monomer combination, so that ophthalmic lens has required hardness, repellency (repellency) and opening speed (opening speed) as main raw.After adding the tinting material that obtains in linking agent, polymerization starter, ultraviolet absorbers and the above-mentioned preparation, this mixture is put into die cavity (mold form) or container, carry out polymerization then.Because tinting material and intraocular lens material (for example (methyl) acrylate) copolymerization, so tinting material wash-out from soft body material hardly.
Although the red type tinting material that yellow type tinting material that above-mentioned general formula I is represented or general formula I I represent can use separately, the preferred combination of using these tinting materials is more to be similar to the human lenticular color of yellowing owing to wearing out.Under the situation of the combination of using these tinting materials, the content of the yellow colorants that general formula I is represented is preferably 0.001 weight % or bigger, but be no more than 0.1 weight %, 0.003 weight % or bigger more preferably, but be no more than 0.03 weight %, the total amount of the soft body material of using based on the intraocular lens material of acquisition like this (coloured body material).On the other hand, the content of the red stain that general formula I I represents is preferably 0.0001 weight % or bigger, but be no more than 0.01 weight %, more preferably 0.0003 weight % or bigger, but be no more than 0.03 weight %, the total amount of the soft body material of using based on the intraocular lens material of acquisition like this (coloured body material).Using with lower ratio under these tinting material situations, so the colour soft body material that obtains only has unconspicuous color, and it is meaningless therefore to add these tinting materials.Using with higher ratio under the situation of these tinting materials, so the soft body material that obtains can not actually use because tone is too dark.
Because soft body material at room temperature should be softness and flexible, so the ratio of components of various (methyl) acrylic acid or the like copolymerisable monomer is determined in the following manner, this mode makes generation preferably have 10 ℃ or lower, more preferably has the soft body material of 5 ℃ or lower glass transition temp.
As for the linking agent that uses in the polymerization, can use by ethylene glycol bisthioglycolate (methyl) acrylate, 1 4-butyleneglycol two (methyl) acrylate, 1, the linking agent of representative such as 6-hexylene glycol two (methyl) acrylate.As for polymerization starter, preferably use 2,2-Diisopropyl azodicarboxylate, the two methyl pentane nitriles of azo, bitter almond oil camphor, methyl-o-benzoyl yl benzoic acid ester etc.
Preferred embodiment as for the UV absorption agent, can mention by 2-(2 '-hydroxyl-5 '-the methacryloxyethyl phenyl)-the coupling type benzotriazole category UV absorption agent of 2H-benzotriazole representative and by the coupling type benzophenone UV absorption agent of 2-hydroxyl-5-glycidyl benzophenone representative etc.
This polymerization can be legal by hot polymerization, the UV polymerization waits and carries out, although it changes with the polymerization starter that is added.For example by being refrigerated to the degree that allows cutting, the colour soft body material that hardens and so obtain.Then, be cut to desired shape.So, can obtain the colour soft ophthalmic lens.Perhaps, the colour soft ophthalmic lens can followingly obtain: with main raw, linking agent, polymerization starter, UV absorption agent and tinting material are introduced in the die cavity, then polymerization and this mixture that hardens.
Although use at room temperature be the soft body material of flexible as material to be colored in this embodiment, the present invention is not limited to this.That is to say that tinting material of the present invention also can be used for by at room temperature being in the ophthalmic lens made of non-flexible hard substrate material.Tinting material of the present invention not only can be used in the ophthalmic lens, also can be used in other eyepiece, for example in the contact lens.Eyepiece of the present invention both can be used in the monolithic type product with material, also can be used in three type products, optical element and supporting member are molded over together with being integrated in the described monolithic type product, construct optical element and supporting member in described three type products separately, then they are being integrated.
Embodiment
(embodiment 1)
＜preparation eyepiece yellow colorants 4-(5 '-hydroxyl-3 '-methyl isophthalic acid '-phenyl-4 '-the pyrazolyl methylene radical)-1-(4 '-the methacryloxy aminomethyl phenyl)-3-antazoline base-5-ketone 〉
Under argon gas stream, with 3-methyl isophthalic acid-phenyl-2-pyrazolinyl-5-ketone (150 grams, 861mmol) be added into dry DMF (dimethyl formamide) (210ml) in, and with ice-cooled.At 2-9 ℃, in 30 minutes introversive dropwise add in it phosphoryl chloride (57.0ml, 629mmol), the mixture 2.5 hours of reaction gained in the time of 40-50 ℃ then.After being cooled to room temperature, in 1 hour, it dropwise is added in the frozen water (3.1kg).Next, in the water-bath with 24 ℃ of its immersions, and stirred 16 hours.Filter the crystal that collecting precipitation comes out, (139.5 grams 692mmol), are yellow crystals thereby obtain compound that above-mentioned general formula III represents.
Under argon gas stream, (204.5 grams 937mmol) are added in the anhydrous chloroform (10.2L) with 4-(3-methyl-5-oxo-2-pyrazolinyl-1-yl) phenylformic acid.Add triethylamine (1.02L, 7.34mol) afterwards, with the mixture of ice-cooled gained.At 1-7 ℃, in 20 minutes introversive its dropwise add the chlorocarbonic acid ethyl ester (511mL, 3.13mol), the mixture 2 hours of reaction gained in the time of 16-21 ℃.After with the THF extraction, at room temperature, in 6 minutes, in it, add sodium borohydride (85.1 grams, aqueous solution 2.25mmol) (2.45L).When 28-35 ℃ of reaction after 2 hours, enriched mixture under reduced pressure.In the aqueous solution of acquisition like this, add 5% hydrochloric acid (900mL), thereby the pH value is adjusted to 4.Next, with chloroform (4L * 3) extraction.Use chloroform/methanol as launching solvent, by the column chromatography purification extract.So, the compound that acquisition general formula X II represents (99.6 grams, 488mmol).
The compound that general formula III is represented (98.7 grams, 488mmol) and the compound represented of general formula X II be added in the acetate (540mL), in 30 minutes, with this mixture heating up to 104 ℃.When after 15 minutes, it being cooled to room temperature, and in it, adding methyl alcohol (1.43L) 104-113 ℃ of backflow.When 1-3 ℃ stir 2 hours after, filter the crystal that collecting precipitation obtains, and use chloroform/methanol as launching solvent, pass through column chromatography purification.So (78.6 grams 277mmol), are yellow crystals to the compound that acquisition general formula X III represents.
The compound that above-mentioned general formula V represents (wherein n is 1).
The compound that the general formula X III that so obtains is represented (78.6 grams 277mmol) are added in the anhydrous methylene chloride (11.8L), and in it, add methacrylic acid (23.9 grams, 277mmol) and 4-dimethylaminopyridine (44.5 restrain, 364mmol).At 17 ℃, in 20 minutes, add N-ethyl-N '-(3-dimethylaminopropyl) carbodiimide hydrogen chlorate (75.4 grams, 394mmol), then this mixture was reacted 19 hours again, use methylene dichloride then, pass through column chromatography purification as launching solvent.By the compound of drying under reduced pressure purifying acquisition at room temperature, (60.9g 133mmol), is yellow crystals to the eyepiece that acquisition general formula X IV represents with the target tinting material.
General formula I represents that (wherein Y is CH to compound
3With n be 1).
＜preparation eyepiece red stain 1-[4 '-4 " the methacryloxyethyl phenylazo) phenylazo]-beta naphthal 〉
At room temperature, (97.8 grams 940mmol) are dissolved in the water (4.73L), and (76.3 grams 940mmol), stirred 10 minutes then to add 37% formlinata aquae concentratac in it with sodium bisulfite.Then add 4-amino-benzene ethyl alcohol (87.5g, 940mmol).After determining to form homogeneous solution, at room temperature this solution of restir is 1.5 hours, obtains solution A.
The vitriol oil (175mL) is dissolved in the water (3.5L).(129 grams 940mmol) afterwards, add ice (875 gram), and mixture are cooled to 1 ℃ in it when adding aniline.(69.7 grams 1.01mol) be dissolved in the water (350L), and at-1 to 1 ℃, the solution with gained in 20 minutes dropwise are added in the said mixture with Sodium Nitrite.After 30 minutes, obtain solution B-1 to 1 ℃ of reaction.
Be added in the solution A solution B is disposable, and 20 ℃ of reactions 30 minutes.Further, in it, add sodium hydroxide (347 grams, 8.68mol)/water (2.28L).In 3 hours, with the mixture heating up to 95 of gained ℃, then 94-101 ℃ of reaction 2 hours.After being cooled to room temperature, the tarry product that filtering-depositing comes out washes with water, and uses methanol extraction.By under reduced pressure concentrating, obtain the tarry product (105 gram) of burgundy.Then, use toluene/ethyl acetate=7/3 as launching solvent, by column chromatography purification, (39.8 grams 165mmol), are the yellowish brown crystal to obtain compound that general formula X V represents thus.
(75.6 grams 313mmol) are added in concentrated hydrochloric acid (90.9mL)/water (1.66L) compound that general formula X V is represented, and add ice (600 gram) with ice-cooled.Next, at-1 to 0 ℃, in 5 minutes, in it, dropwise add Sodium Nitrite (27.2 grams, 394mmol)/water (150mL), and in 0 to 1 ℃ of mixture that stirs gained down 30 minutes.With this solution disposable be added into by with 2-Naphthol (45.1 the gram, 313mmol) be dissolved in sodium hydroxide (38.0 the gram, 950mmol)/water (3.8L) in and the preparation solution in.After reaction 3 hours, filter the crystal that collecting precipitation comes out, and wash with water.Use THF as launching solvent, by column chromatography purification, (107.7 grams 271mmol), are red crystals to obtain compound that general formula X VI represents.
The compound that above-mentioned general formula X I represents (wherein n is 2).
The compound that general formula X VI is represented (107.7 grams 271mmol) are added in the anhydrous methylene chloride (9.96L), and in it, add methacrylic acid (21.6 grams, 251mmol) and 4-dimethylaminopyridine (36.8 restrain, 301mmol).Next, in 10 minutes, interpolation N-ethyl-N '-(dimethylaminopropyl) carbodiimide hydrogen chlorate in it (62.5g, 326mmol).After reaction 18 hours, use toluene/ethyl acetate=conduct in 50: 1 to launch solvent, by column chromatography, the purification reaction mixture.So (27.9g 61.1mmol), is red crystals to the eyepiece that acquisition general formula X VII represents with the target tinting material.
(wherein Y is CH to the compound that above-mentioned general formula I I represents
3With n be 2).
Yellow colorants with the above-mentioned acquisition of 0.006 weight %, 0.0008 the red stain of weight %, 53.9 the ethylene glycol phenyl ether acrylate of weight %, 39.7 the positive butyl ester of the methacrylic ester of weight %, 4.0 the n-butyl acrylate of weight %, 2.0 weight % as 1 of linking agent, the 4-butylene glycol dimethacrylate, 0.3 the 2-as ultraviolet absorbers of weight % (2 '-hydroxyl-5 '-methacryloxypropyl-3 '-tert-butyl-phenyl)-5-chloro-2H-benzotriazole and trace be as 2 of polymerization starter, the 2-Diisopropyl azodicarboxylate mixes, in the test tube of packing into then.Then, this mixture of polymerization is 24 hours in 60 ℃ thermostat container, and polymerization is 24 hours in 95 ℃ baking oven, and polymerization in 95 ℃ vacuum oven then obtains orange ophthalmic lens thus with soft body material (eyepiece body material).
To be shaped to diameter be 6mm and thickly be the sheet of 1mm with body material with the ophthalmic lens that so obtains, and measure its transmissivity (HITACHI, the spectrophotometer U-4000 of Ltd. manufacturing).The results are shown in the table 1.As shown in table 1, the nearly all light of the sheet absorbing wavelength of acquisition in 350nm to 400nm ultraviolet region, also the light of absorbing wavelength in 400nm to 500nm promptly, shows near human lenticular optical absorption property.
The sheet that obtains is immersed in the acetone, and in 60 ℃ baking oven, preserved 72 hours.When after so preserving 72 hours under the heating, take out this sheet, and observe its outward appearance.The result is not observe decolouring.And, measure transmissivity.The result is not observe transmission change.
(comparative example 1)
Prepare ophthalmic lens with orange soft body material with the condition identical with embodiment 1, different is: use yellow colorants Yellow AG (by NIPPON KAYAKU, CO.Ltd. make) and red stain Sudan I (by KISHIDA CHEMICAL Co., Ltd. makes).As embodiment 1, to be shaped to diameter be 6mm and thickly be the sheet of 1mm with body material with the ophthalmic lens that so obtains, and use acetone treatment.After with acetone treatment, this sheet decolours fully.
(comparative example 2)
Prepare ophthalmic lens with blue soft body material with the condition identical with embodiment 1, different is: use tinting material Kayalon Polyster Navy Blue ES-SF300 R-822 (by NIPPONKAYAKU, CO.Ltd. makes).As embodiment 1, to be shaped to diameter be 6mm and thickly be the sheet of 1mm with body material with the ophthalmic lens that so obtains, and use acetone treatment.After with acetone treatment, this sheet decolours fully.
The application is incorporated herein by reference its full content at this based on the Japanese patent application JP 2004-326341 that submitted on November 10th, 2004, as abundant description its.
Claims (9)
1. eyepiece tinting material, it is represented by following general formula I:
Wherein Y represents H or CH
3N is the integer of 1-5.
2. the tinting material of claim 1, wherein Y represents CH
3With n be 1.
3. eyepiece tinting material, it is represented by following general formula I I:
Wherein Y represents H or CH
3N is the integer of 1-5.
4. the tinting material of claim 3, wherein Y represents CH
3With n be 2.
5. coloured eyepiece material, it comprises following at least a:
The tinting material that following general formula I is represented:
Wherein Y represents H or CH
3N is the integer of 1-5; With
The tinting material that following general formula I I represents:
Wherein Y represents H or CH
3N is the integer of 1-5.
6. the material of claim 5, it comprises the tinting material that tinting material that general formula I is represented and general formula I I represent.
7. the material of claim 6, wherein the amount of the tinting material represented of general formula I is the 0.001-0.1 weight % of the material of the tinting material that comprises that tinting material that general formula I is represented and general formula I I represent, and the amount of the tinting material that general formula I I represents is the 0.0001-0.01 weight % of the material of the tinting material that comprises that tinting material that general formula I is represented and general formula I I represent.
8. the material of claim 7, wherein the amount of the tinting material represented of general formula I is the 0.003-0.03 weight % of the material of the tinting material that comprises that tinting material that general formula I is represented and general formula I I represent, and the amount of the tinting material that general formula I I represents is the 0.0003-0.003 weight % of the material of the tinting material that comprises that tinting material that general formula I is represented and general formula I I represent.
9. the material of claim 7, the glass transition temp of the material of the tinting material that tinting material of representing comprising general formula I and general formula I I represent is 10 ℃ or lower.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2005101248626A CN1970640B (en) | 2005-11-23 | 2005-11-23 | Ocular colorant and colorful ocular material using same |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2005101248626A CN1970640B (en) | 2005-11-23 | 2005-11-23 | Ocular colorant and colorful ocular material using same |
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| CN1970640A CN1970640A (en) | 2007-05-30 |
| CN1970640B true CN1970640B (en) | 2011-08-31 |
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| KR101786302B1 (en) * | 2016-03-03 | 2017-10-17 | (주)메디오스 | The method for producing blue light blocking soft contact lens |
Citations (6)
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|---|---|---|---|---|
| US3984199A (en) * | 1972-03-16 | 1976-10-05 | Cassella Farbwerke Mainkur Aktiengesellschaft | Water-insoluble monoazo dyestuffs |
| EP0131468A2 (en) * | 1983-07-11 | 1985-01-16 | Iolab Corporation | Ultraviolet absorbing polymers comprising 2-hydroxy-5-acrylyloxalkylphenyl-2H-benzotriazoles |
| US5662707A (en) * | 1993-10-18 | 1997-09-02 | Alcon Laboratories, Inc. | Polymerizable yellow dyes and their use in ophthalmic lenses |
| EP0899590A2 (en) * | 1997-08-29 | 1999-03-03 | Nidek Co., Ltd | Ultraviolet absorbing base material |
| CN1290699A (en) * | 1999-04-07 | 2001-04-11 | 保谷健康护理株式会社 | New pyrazolone compound and eye plastic lens made therefrom |
| CN1510457A (en) * | 2002-12-20 | 2004-07-07 | 尼德克株式会社 | Colouring pigment of eye lense and stained eye lense therewith |
-
2005
- 2005-11-23 CN CN2005101248626A patent/CN1970640B/en active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3984199A (en) * | 1972-03-16 | 1976-10-05 | Cassella Farbwerke Mainkur Aktiengesellschaft | Water-insoluble monoazo dyestuffs |
| EP0131468A2 (en) * | 1983-07-11 | 1985-01-16 | Iolab Corporation | Ultraviolet absorbing polymers comprising 2-hydroxy-5-acrylyloxalkylphenyl-2H-benzotriazoles |
| US5662707A (en) * | 1993-10-18 | 1997-09-02 | Alcon Laboratories, Inc. | Polymerizable yellow dyes and their use in ophthalmic lenses |
| EP0899590A2 (en) * | 1997-08-29 | 1999-03-03 | Nidek Co., Ltd | Ultraviolet absorbing base material |
| CN1290699A (en) * | 1999-04-07 | 2001-04-11 | 保谷健康护理株式会社 | New pyrazolone compound and eye plastic lens made therefrom |
| CN1510457A (en) * | 2002-12-20 | 2004-07-07 | 尼德克株式会社 | Colouring pigment of eye lense and stained eye lense therewith |
Non-Patent Citations (1)
| Title |
|---|
| JP特开平7-24052A 1995.01.27 |
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