CN110804131B - Preparation method of long-acting photochromic compound based on cyclodextrin modification and application of long-acting photochromic compound in contact lenses - Google Patents
Preparation method of long-acting photochromic compound based on cyclodextrin modification and application of long-acting photochromic compound in contact lenses Download PDFInfo
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- CN110804131B CN110804131B CN201910985785.5A CN201910985785A CN110804131B CN 110804131 B CN110804131 B CN 110804131B CN 201910985785 A CN201910985785 A CN 201910985785A CN 110804131 B CN110804131 B CN 110804131B
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F251/00—Macromolecular compounds obtained by polymerising monomers on to polysaccharides or derivatives thereof
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
- C08B37/0012—Cyclodextrin [CD], e.g. cycle with 6 units (alpha), with 7 units (beta) and with 8 units (gamma), large-ring cyclodextrin or cycloamylose with 9 units or more; Derivatives thereof
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K9/00—Tenebrescent materials, i.e. materials for which the range of wavelengths for energy absorption is changed as a result of excitation by some form of energy
- C09K9/02—Organic tenebrescent materials
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- G—PHYSICS
- G02—OPTICS
- G02C—SPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
- G02C7/00—Optical parts
- G02C7/02—Lenses; Lens systems ; Methods of designing lenses
- G02C7/04—Contact lenses for the eyes
- G02C7/049—Contact lenses having special fitting or structural features achieved by special materials or material structures
Abstract
The invention relates to a long-acting photochromic compound based on cyclodextrin modification and application thereof in contact lenses, wherein the cyclodextrin modified compound comprises the following components: at least one photochromic group; at least one hindered amine or hindered phenol light stabilizer group; at least one ultraviolet light absorber group; the long-acting photosensitive cyclodextrin compound is formed by bonding the photochromic micromolecules, the light stabilizer and the ultraviolet absorber into the cyclodextrin molecules, so that the light resistance of photochromic groups is obviously enhanced under the action of the light stabilizer and the ultraviolet absorber, and the photochromic service life of the photochromic contact lens is prolonged.
Description
Technical Field
The invention belongs to the field of functional molecular materials, relates to the technical field of photochromism, and particularly relates to a preparation method of a long-acting photochromic compound based on cyclodextrin modification and application of the long-acting photochromic compound in contact lenses.
Background
As with human skin, our eyes also need to be "sun protected". The long-term exposure of human eyes to ultraviolet rays can cause asthenopia, strabismus and visual deterioration, and serious eye diseases such as cataract and the like. Therefore, the photochromic contact lenses which can automatically adjust the color depth according to the ultraviolet intensity and the temperature, have rich colors, are convenient and can protect eyes have great market value. Important characteristics of photochromic contact lenses are the facility to adapt to various light conditions, providing optimum light transmission for ambient brightness, and in particular all weather uv radiation and sun glare protection.
At present, the research on photochromic contact lenses focuses on two major directions of photochromic ink and photochromic material introduced into a substrate material of the contact lenses, but the existing schemes have defects. A method of manufacturing photochromic contact lenses, such as the type represented by CN200380101704.8, discloses contact lenses having photochromic materials in the central or pupillary region of the lens and a method of manufacturing such lenses by incorporating photochromic monomers into the contact lenses, primarily by curing, wherein the controllability of the curing operation involved is poor and the photochromic monomers are also likely to self-polymerize and free; for another example, CN103087581A, the patent describes a photochromic ink printing paste, in which photochromic dye is mixed into the ink by doping, and the dissociation of photochromic small molecules also occurs; further, as a method of manufacturing colored contact lenses of the type represented by CN1961223, a method of manufacturing colored silicone hydrogel contact lenses is provided. Although the photochromic glasses belong to colored glasses, the thinking is developed for the research and development of the photochromic glasses, and the photochromic glasses have no photochromic performance; for another example, CN104059319A, the patent discloses a method for infiltrating 6 '-azacyclo-substituted-9' -acyloxy-esterified spirooxazine photochromic material onto the surface of contact lens by infiltration. The surface of the contact lens is covered in a permeation mode, on one hand, the covering of the photochromic material on the surface of the contact lens cannot be controlled to be uniform, the attractiveness of the contact lens is affected, and on the other hand, the permeation method inevitably causes the migration of the photochromic material, so that the potential safety hazard of wearing of human eyes is caused. Moreover, none of the above patents address the aging, i.e., useful life, of contact lenses incorporating photochromic materials.
Disclosure of Invention
In view of the defects of photochromic contact lenses and the limitations of aging yellowing, photochromic failure and the like of photochromic materials in the contact lenses, the invention provides a preparation method of a long-acting photochromic compound based on cyclodextrin modification and application of the long-acting photochromic compound in the contact lenses. Photochromic groups, hindered amine light stabilizer groups and ultraviolet absorbent groups are introduced into cyclodextrin molecules, and the photosensitive efficiency of the photochromic contact lenses is enhanced, the service life of the contact lenses is prolonged and the yellowing problem is solved through the coordination effect among the three groups.
In order to achieve the purpose, the technical scheme adopted by the invention is as follows:
a long-acting photochromic compound based on cyclodextrin modification, the cyclodextrin-modified compound comprising the following components: 1) at least one photochromic group; 2) at least one hindered amine or hindered phenol light stabilizer group; 3) at least one ultraviolet light absorber group.
Preferably, the photochromic group comprises photochromic small molecules, and the photochromic small molecules are at least one of spiropyrans and derivatives thereof, spirooxazines and derivatives thereof; the photochromic small molecule comprises a reactive group, and the reactive group is carboxyl or alkynyl.
Preferably, the number of the photochromic group substituted for the cyclodextrin group is 1 to 4.
Preferably, the hindered amine light stabilizer group is an amino group; the number of the hindered amine light stabilizer groups for substituting cyclodextrin groups is 0-2.
Preferably, the cyclodextrin molecule is alpha-cyclodextrin and its derivatives, beta-cyclodextrin and its derivatives.
Preferably, the group of the cyclodextrin derivative is azide or carboxyl.
Preferably, the ultraviolet light absorber group is an amino group; the absorption wavelength of the ultraviolet light absorber is 200-340 nm.
Preferably, the number of the cyclodextrin groups substituted by the ultraviolet absorbent group is 1 to 2.
The long-acting photochromic compound modified based on cyclodextrin is applied to the preparation of contact lenses.
The addition proportion of the photochromic compound in the base material of the contact lens is 0.1 to 10 percent.
This patent chooses natural macromolecule cyclodextrin as the carrier of photochromism micromolecule for use to branch grafting hinders amine light stabilizer molecule and ultraviolet absorber molecule on cyclodextrin simultaneously, photochromism cyclodextrin after will modifying is applied to the contact lens matrix material system in, fix photochromism micromolecule with cyclodextrin, reduce the micromolecule migration or separate out, reduce the cytotoxicity of photochromism material, increase biocompatibility, the tubular structure of cyclodextrin has also improved contact lens's oxygen permeability simultaneously. And the photochromic material, the hindered amine or hindered phenol light stabilizer molecule and the ultraviolet absorbent molecule are grafted in the same molecule to generate a synergistic effect, so that the service life of the photochromic contact lens is prolonged, the photochromic effect is more obvious, and the aging and yellowing problems are solved within a certain time range.
The invention bonds photochromic micromolecules, light stabilizer and ultraviolet absorber into cyclodextrin molecule to form the long-acting photosensitive cyclodextrin compound, and has the following advantages: 1) under the action of a light stabilizer and an ultraviolet light absorber, the light resistance of the photochromic group is obviously enhanced, and the color change life of the photochromic contact lens is prolonged; 2) the photochromic group is fixed on the cyclodextrin biomacromolecule, so that the migration of the cyclodextrin biomacromolecule from the contact lens matrix is difficult, and the problems of easy migration and overflow of a single photochromic micromolecule added into the contact lens are solved. Meanwhile, two molecules of photochromic materials are grafted on one cyclodextrin molecule, and compared with the addition of a single photochromic micromolecule, the photochromic density is increased, and the photochromic effect is more obvious. 3) The biomacromolecule cyclodextrin enables the color-changing compound to have good biocompatibility. 4) The cyclodextrin is in a hollow cylinder shape with wide top and narrow bottom, and two open ends, so that oxygen molecules can pass through the cyclodextrin, and the oxygen permeability of the contact lens is improved;
compared with the prior art, the invention has the following beneficial effects due to the adoption of the technology:
1. firstly, the cyclodextrin is a macromolecule, and photochromic micromolecules, ultraviolet absorbers and hindered amine (or hindered phenol) light stabilizers are fixed on the cyclodextrin, so that migration or precipitation of the photochromic micromolecules, the ultraviolet absorbers and the hindered amine (or hindered phenol) light stabilizers is reduced; secondly, the cyclodextrin is used as a biological material and has good biocompatibility, so that the photochromic material and the hindered amine light stabilizer have better dispersibility in the contact lens, and the cytotoxicity of the photochromic small molecule and the hindered amine light stabilizer to the matrix material is reduced; in addition, the cyclodextrin unique molecular capsule space structure can improve the oxygen permeability of the contact lens material, so that the photochromic contact lens prepared by the method has the advantages of excellent photochromic property, good biocompatibility and high oxygen permeability;
2. according to the invention, at least two molecules of photochromic materials are grafted on one cyclodextrin molecule, and compared with the addition of a single photochromic micromolecule, the photochromic density is increased, and the photochromic effect is more obvious;
3. according to the invention, hindered amine (or hindered phenol) photostable groups and ultraviolet absorbent groups are grafted on cyclodextrin, firstly, hindered amine photostabilizer (or hindered phenol), ultraviolet absorbent and photochromic molecules form a coordination effect, the coordination effect is formed among the hindered amine photostabilizer, the ultraviolet absorbent and the photochromic molecules, the coordination effect is applied to a contact lens material matrix by a doping, group reaction or copolymerization method, and the photochromic molecules are enhanced in photosensitive stability and anti-fatigue capability by the synergistic effect between the photochromic small molecules and the hindered amine (or hindered phenol) photostabilizer, namely, the hindered amine (or hindered phenol) photostabilizer; the ultraviolet absorbent absorbs ultraviolet rays in a non-excitation waveband, so that the aging of the contact lens caused by the ultraviolet rays is reduced, and the service life of the contact lens is prolonged;
4. the response time of the photochromic contact lens obtained by the invention to sunlight is 0-5s, and the half fading time is 0-10 s, so that the application requirements of human eyes can be met;
5. the preparation method is easy to implement, is suitable for hydrophilic gel, silicon hydrogel, fluorosilicone hydrogel and silicon rubber contact lens materials in the current market, and has high market value.
Drawings
FIG. 1 is a UV-VIS absorption spectrum of a cyclodextrin-modified long-acting photochromic compound prepared in accordance with one embodiment;
FIG. 2 is a graph of the UV-VIS transmission spectra of a cyclodextrin modified long-acting photochromic compound prepared in accordance with one embodiment;
Detailed Description
The present invention will be further illustrated with reference to the following specific embodiments.
Example 1:
preparation of Spirooxazine-COOH (photochromic Material 1)
Equimolar amounts of 1- (. beta. -carboxyethyl) -2, 3, 3-trimethylindolium iodonium, 1-nitrosonaphthol, and triethylamine were dissolved in 80mL of ethanol and refluxed for 3 hours to give Spirooxazine-COOH, which was designated as photochromic material 1.
Example 2:
preparation of Spiropyran-COOH (photochromic Material 2)
Equimolar amounts of 1- (. beta. -carboxyethyl) -2, 3, 3-trimethyl-3H-indolium iodide and 2-hydroxy-5-nitrobenzaldehyde were dissolved in 10mL of acetone and refluxed for 4 hours to give Spiropyran-COOH, which was designated as photochromic material 2.
Example 3:
preparation of Spirooxazine-OH (photochromic Material 3)
1-nitroso-2, 7-dihydroxynaphthalene, 1, 2, 3, 3-tetramethyl-3H-indolium iodide, in ethanol and triethylamine, mixing evenly, refluxing and reacting for 5 hours at 80 ℃, obtaining Spirooxazine-OH which is marked as photochromic material 3.
Example 4:
preparation of photochromic hydrophilic gel contact lenses 1
1) Preparation of carboxymethyl- β -cyclodextrin: transferring a proper amount of 25 mass percent sodium hydroxide solution into a round-bottom flask, adding a certain amount of beta-cyclodextrin, stirring while heating to completely dissolve the beta-cyclodextrin, dropwise adding a certain amount of chloroacetic acid aqueous solution into the beta-CD alkaline solution while stirring, and reacting at room temperature for 9 hours to obtain the carboxymethyl-beta-cyclodextrin.
2) And (2) taking carboxymethyl-beta-cyclodextrin with equal molecular weight, a hindered amine light stabilizer Luchem HA-R100 and an ultraviolet absorbent 2- (4-benzyl-3-p-hydroxyphenyl) acethydrazide with equal molecular weight, dispersing into 100mL of water mixed solution containing equal molar weight of NHS and EDC, and reacting for 12 hours to obtain the composite beta-cyclodextrin 1.
3) The equal molecular weight of the composite beta-cyclodextrin 1 and Spirooxazine-COOH (photochromic material 1) is dissolved in 50mL of N, N-dimethylformamide, 0.18g of potassium carbonate is added, and the mixture is refluxed for 3 hours at 100 ℃ under the protection of nitrogen, so that the photochromic compound 1 is obtained.
4) Dissolving photochromic compound 1 (0.1%) in hydroxyethyl methacrylate, initiator and cross-linking agent, mixing, injecting into a mold, and copolymerizing at 100 deg.C. And soaking the lens in normal saline for 30min to obtain the photochromic hydrophilic gel contact lens 1.
Example 5:
preparation of photochromic hydrophilic gel contact lenses 2
1) And (2) taking carboxymethyl-beta-cyclodextrin with equal molecular weight, a hindered amine light stabilizer Luchem HA-R100 and an ultraviolet absorbent 2- (4-benzyl-3-p-hydroxyphenyl) acethydrazide with equal molecular weight, dispersing into 100mL of water mixed solution containing equal molar weight of NHS and EDC, and reacting for 12 hours to obtain the composite beta-cyclodextrin 1.
2) Compound beta-cyclodextrin 1 and Spiropyran-COOH (photochromic material 2) with equal molecular weight are taken and dissolved in 50mL of N, N-dimethylformamide, 0.18g of potassium carbonate is added, and the mixture is refluxed for 3 hours at 100 ℃ under the protection of nitrogen, so that the photochromic compound 2 is obtained.
3) Dissolving photochromic compound 2 (1%) in hydroxyethyl methacrylate, initiator and cross-linking agent, mixing, injecting into a mould, and copolymerizing at 100 deg.C. And soaking the lens in normal saline for 30min to obtain the photochromic hydrophilic gel contact lens 2.
Example 6:
preparation of photochromic hydrophilic gel contact lenses 3
1) Preparation of carboxymethyl- β -cyclodextrin: transferring a proper amount of 25 mass percent sodium hydroxide solution into a round-bottom flask, adding a certain amount of beta-cyclodextrin, stirring while heating to completely dissolve the beta-cyclodextrin, dropwise adding a certain amount of chloroacetic acid aqueous solution into the beta-CD alkaline solution while stirring, and reacting at room temperature for 9 hours to obtain the carboxymethyl-beta-cyclodextrin.
2) And (2) taking carboxymethyl-beta-cyclodextrin with equal molecular weight, hindered amine light stabilizer Luchem HA-R100 and ultraviolet absorbent 2- (4-benzyl-3-p-hydroxyphenyl) acethydrazide with equal molecular weight, dispersing into 100mL of water mixed solution containing NHS and EDC with equal molar weight, and reacting for 12 hours to obtain the composite beta-cyclodextrin 1.
3) The equal molecular weight of the composite beta-cyclodextrin 1, Spirooxazine-COOH (photochromic material 1) and Spiropyran-COOH (photochromic material 2) are dissolved in 50mLN, N-dimethylformamide, 0.18g of potassium carbonate is added, and the mixture is refluxed for 3 hours at 100 ℃ under the protection of nitrogen, so that the photochromic compound 3 is obtained.
4) Dissolving photochromic compound 3 (5%) in hydroxyethyl methacrylate, initiator and cross-linking agent, mixing, injecting into a mould, and copolymerizing at 100 deg.C. And soaking the lens in normal saline for 30min to obtain the photochromic hydrophilic gel contact lens 3.
Example 7:
1. preparation of photochromic Compound 4
1)N 3 -synthesis of beta-cyclodextrin. Transferring a proper amount of 25 percent (mass percentage concentration) sodium hydroxide solution into a round-bottom flask, adding a certain amount of beta-cyclodextrin, stirring the beta-cyclodextrin under warm conditions to completely dissolve the beta-cyclodextrin, dropwise adding a mixed solution of p-toluenesulfonic acid and acetonitrile, and reacting for 6 hours at normal temperature to obtain a target product.
2) And (3) synthesizing propynyl spirooxazine. Equal molecular weight of Spirooxazine-OH (photochromic material 3) and bromopropyne are taken to be dissolved in dichloromethane and triethylamine and stirred for 10 hours at room temperature to obtain the target product.
3) And (3) synthesizing beta-cyclodextrin-Spirooxazine-OH. Taking equal molecular weight of N 3 Dissolving beta-cyclodextrin and propynyl spirooxazine in methanol solution, adding CuBr 2 And refluxing the aqueous solution of pentamethyl-tetraethylene amine and the DMF solution of azoisobutyronitrile at 60 ℃ for 30 minutes to obtain the beta-cyclodextrin-Spirooxazine-OH photochromic material 4.
4) Preparing carboxymethyl-beta-cyclodextrin on the basis of a beta-cyclodextrin-Spirooxazine-OH photochromic material 4: transferring a proper amount of 25 mass percent sodium hydroxide solution into a round-bottom flask, adding a certain amount of beta-cyclodextrin, stirring while heating to completely dissolve the beta-cyclodextrin, dropwise adding a certain amount of chloroacetic acid aqueous solution into the beta-CD alkaline solution while stirring, and reacting at room temperature for 9 hours to obtain the carboxymethyl-beta-cyclodextrin.
5) Equal molecular weight carboxymethyl-beta-cyclodextrin, hindered amine light stabilizer Luchem HA-R100 and ultraviolet absorbent 2- (4-benzyl-3-p-hydroxyphenyl) acethydrazide are taken and dispersed into 100mL water mixed solution containing equal molar weight NHS and EDC, and the photochromic compound 4 is obtained after reaction for 12 hours.
2. Preparation of photochromic hydrophilic gel contact lenses 4
6) Dissolving photochromic compound 4 (10%) in hydroxyethyl methacrylate, initiator and cross-linking agent, mixing, injecting into a mould, and copolymerizing at 100 deg.C. And soaking the lens in normal saline for 30min to obtain the photochromic hydrophilic gel contact lens 4.
The photochromic contact lenses produced in examples 4-7 were tested for performance and the results are shown in Table 1:
TABLE 1 Properties of photochromic contact lenses
| Photochromic contact lens serial number | Response time to ultraviolet light | Half fade time t 1/2 |
| 1 | 1-2s | 5-6s |
| 2 | 1-2s | 6-10s |
| 3 | 1-2s | 6-10s |
| 4 | 1-2s | 5-6s |
FIG. 1 is a graph showing UV-VIS absorption spectra of cyclodextrin-modified long-acting photochromic compound (Spirooxazine-COOH) prepared in example one, irradiated with UV light for 0s, 10s, 20s, and 30s, respectively.
FIG. 2 is a graph showing UV-VIS spectra of cyclodextrin-modified long-acting photochromic compound (Spirooxazine-COOH) prepared in example one, irradiated with UV light for 0s, 10s, 20s, and 30s, respectively.
The above embodiments are merely preferred embodiments of the present invention, and should not be construed as limiting the present invention, the scope of the present invention should be defined by the claims, and equivalents including technical features described in the claims are intended to be included in the scope of the present invention, that is, equivalent modifications within the scope of the present invention are also within the scope of the present invention.
Claims (10)
1. A long-acting photochromic compound based on cyclodextrin modification is characterized in that the cyclodextrin modified compound comprises the following components: 1) at least one photochromic group; 2) at least one hindered amine or hindered phenol light stabilizer group; 3) at least one ultraviolet light absorber group.
2. A long-acting photochromic compound modified based on cyclodextrin as claimed in claim 1, wherein: the photochromic group is at least one of spiropyrans and derivatives thereof, spirooxazines and derivatives thereof; the photochromic group comprises a reactive group, and the reactive group is a carboxyl group or an alkynyl group.
3. A long-acting photochromic compound modified based on cyclodextrin as claimed in claim 2, wherein: the number of the photochromic group substituted cyclodextrin group is 1-4.
4. The long-acting photochromic compound modified based on cyclodextrin as claimed in claim 1, wherein: the number of hindered amine light stabilizer groups substituted for cyclodextrin groups is 0-2 and is not 0.
5. A long-acting photochromic compound modified based on cyclodextrin as claimed in claim 1, wherein: the cyclodextrin molecule is alpha-cyclodextrin and derivatives thereof or beta-cyclodextrin and derivatives thereof.
6. The long-acting photochromic compound modified based on cyclodextrin as claimed in claim 5, wherein: the group of the cyclodextrin derivative is azide or carboxyl.
7. A long-acting photochromic compound modified based on cyclodextrin as claimed in claim 1, wherein: the absorption wavelength of the ultraviolet light absorber is 200-340 nm.
8. The long-acting photochromic compound modified based on cyclodextrin as claimed in claim 7, wherein: the number of the ultraviolet absorbent groups substituted by cyclodextrin groups is 1-2.
9. Use of long-acting photochromic compounds modified on the basis of cyclodextrins according to claims 1 to 8 for the preparation of contact lenses.
10. Use according to claim 9, characterized in that: the addition proportion of the photochromic compound in the base material of the contact lens is 0.1 to 10 percent.
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| KR20020064267A (en) * | 2002-07-22 | 2002-08-07 | 조경래 | Contact lens that color changed and manufacturing process thereof |
| CN100596332C (en) * | 2008-08-20 | 2010-03-31 | 东南大学 | Medicine-carrying contact lens and preparation method thereof |
| WO2018030257A1 (en) * | 2016-08-10 | 2018-02-15 | 株式会社トクヤマ | Photochromic curable composition, use thereof, and polyrotaxane monomers |
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