CN109422990A - Photochromic ophthalmic lenses and preparation method thereof - Google Patents

Photochromic ophthalmic lenses and preparation method thereof Download PDF

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Publication number
CN109422990A
CN109422990A CN201710724390.0A CN201710724390A CN109422990A CN 109422990 A CN109422990 A CN 109422990A CN 201710724390 A CN201710724390 A CN 201710724390A CN 109422990 A CN109422990 A CN 109422990A
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CN
China
Prior art keywords
photochromic
compound
cyclodextrin
ophthalmic lenses
preparation
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Pending
Application number
CN201710724390.0A
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Chinese (zh)
Inventor
简秀纹
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Hongfujin Precision Industry Shenzhen Co Ltd
Hon Hai Precision Industry Co Ltd
Original Assignee
Hongfujin Precision Industry Shenzhen Co Ltd
Hon Hai Precision Industry Co Ltd
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Priority to CN201710724390.0A priority Critical patent/CN109422990A/en
Publication of CN109422990A publication Critical patent/CN109422990A/en
Pending legal-status Critical Current

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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
    • C08B37/0015—Inclusion compounds, i.e. host-guest compounds, e.g. polyrotaxanes
    • 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
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/20—Esters of polyhydric alcohols or phenols, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/42—Block-or graft-polymers containing polysiloxane sequences
    • C08G77/442—Block-or graft-polymers containing polysiloxane sequences containing vinyl polymer sequences
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04—Homopolymers or copolymers of esters
    • C08L33/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/10—Block- or graft-copolymers containing polysiloxane sequences
    • G—PHYSICS
    • G02—OPTICS
    • G02C—SPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
    • G02C7/00—Optical parts
    • G02C7/10—Filters, e.g. for facilitating adaptation of the eyes to the dark; Sunglasses
    • G02C7/102—Photochromic filters

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Ophthalmology & Optometry (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Molecular Biology (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Materials Engineering (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Eyeglasses (AREA)

Abstract

A kind of preparation method of photochromic ophthalmic lenses, including one photochromic compound-cyclodextrin inclusion compound and a Gel Precursor are provided, the photochromic compound-cyclodextrin inclusion compound is the cyclodextrin that envelope has photochromic compound；Photochromic compound-the cyclodextrin inclusion compound and the gel precursor are mixed to obtain a mixture；And the mixture is placed in a mold and heats the mold, a gel-in-matrix is formed to make the Gel Precursor that polymerization reaction occur, and it is scattered in the photochromic compound-cyclodextrin inclusion compound in the gel-in-matrix, so that the photochromic ophthalmic lenses be made.

Description

Photochromic ophthalmic lenses and preparation method thereof
Technical field
The present invention relates to eye lens field more particularly to a kind of photochromic ophthalmic lenses and this is photochromic ophthalmically acceptable The preparation method of eyeglass.
Background technique
There is photochromic compounds excellent photochromic invertibity can such as under ultraviolet light change colour rapidly, When not having ultraviolet light, primary colors can be restored rapidly, to be expected to obtain in many fields, such as eye lens, biomimetic material field To application.However, it is generally insoluble in water and hydrophilic solvent because photochromic compounds are hydrophobic material, so that its Application range is limited.
Summary of the invention
In view of this, it is necessary to provide a kind of systems for preparing photochromic ophthalmic lenses using photochromic compounds Preparation Method is able to solve problem above.
In addition, there is a need to provide a kind of photochromic ophthalmic lenses as made from above-mentioned preparation method.
The present invention provides a kind of preparation method of photochromic ophthalmic lenses, comprising: provides one photochromic compound-ring Cyclodextrin inclusion compound and a Gel Precursor, the photochromic compound-cyclodextrin inclusion compound are that envelope has photochromicization Close the cyclodextrin of object；Photochromic compound-the cyclodextrin inclusion compound and the gel precursor are mixed to obtain a mixing Object；And the mixture is placed in a mold and heats the mold, to make the Gel Precursor that polymerization reaction occur And a gel-in-matrix is formed, and be scattered in the photochromic compound-cyclodextrin inclusion compound in the gel-in-matrix, to make Obtain the photochromic ophthalmic lenses.
It is described photochromic ophthalmically acceptable the present invention also provides a kind of photochromic ophthalmic lenses, including an eye lens ontology Eyeglass further includes the photochromic compound-cyclodextrin inclusion compound being scattered in the gel-in-matrix, the photochromic compound- Cyclodextrin inclusion compound is the cyclodextrin that envelope has photochromic compound.
In the present invention, since the outer rim of the molecular structure of cyclodextrin is hydrophilic, cyclodextrin inclusion technique, which can be used, to be made Photochromic compound-the cyclodextrin inclusion compound formed has hydrophily, and it is former not change the photochromic compound Some photochromic functions, to make photochromic compound that can have wider application in photochromic ophthalmic lenses.
Detailed description of the invention
Fig. 1 is the structural schematic diagram for the photochromic ophthalmic lenses that a better embodiment of the invention provides.
Main element symbol description
Eye lens ontology 10
Photochromic compound-cyclodextrin inclusion compound 20
Photochromic ophthalmic lenses 100
The present invention that the following detailed description will be further explained with reference to the above drawings.
Specific embodiment
A better embodiment of the invention provides a kind of preparation method of photochromic ophthalmic lenses 100 (please referring to Fig. 1). Wherein, the photochromic ophthalmic lenses 100 can be the frame eyeglasses with photochromic function.The preparation method includes Following steps:
Step 1 provides one photochromic compound-cyclodextrin inclusion compound.
Photochromic compound-the cyclodextrin inclusion compound is the cyclodextrin that envelope has photochromic compound.Specifically, Since the inner cavity of the molecular structure of cyclodextrin is hydrophobic, it is thus possible to provide a hydrophobic binding site and envelope photochromicization Close object.Meanwhile photochromic compound generally has hydrophobicity, and the outer rim of the molecular structure of cyclodextrin is hydrophilic, therefore can adopt Make the photochromic compound-cyclodextrin inclusion compound to be formed that there is hydrophily with cyclodextrin inclusion technique, and does not change institute State the original photochromic function of photochromic compound.
In the present embodiment, the photochromic compound can be selected from spiro-pyrans (spiropyrans), spiral shell pyridine pah (spiroperimidines), diarylethene (diarylethenes), fulgide (fulgides), hexa-aryl bi-imidazole (hexaarylbiimidazole), azobenzene (azobenzenes) and benzodihydropyran (benzopyrylospiran) At least one of Deng.The cyclodextrin can be the modified cyclodextrin after acrylic modified.
The chemical structural drawing of the modified cyclodextrin are as follows:
In the present embodiment, the photochromic compound-cyclodextrin inclusion compound can be made by the following method: by institute It states photochromic compound to be dissolved in one kind of ethyl alcohol, tetrahydrofuran and acetone and form a photochromic solution, the light Causing concentration of the electrochromic compound in the photochromic solution is 0.0001mol/L-0.1mol/L；By the cyclodextrin Yu Shui and form a cyclodextrin aqueous solution, concentration of the cyclodextrin in the cyclodextrin aqueous solution be 0.00001mol/L- 0.1mol/L；Above-mentioned photochromic solution and cyclodextrin aqueous solution are mixed to obtain a mixed solution, so that the cyclodextrin packet Photochromic compound described in network and form the photochromic compound-cyclodextrin inclusion compound；By the photochromic chemical combination Object-cyclodextrin inclusion compound is separated from the mixed solution.
Step 2 provides a Gel Precursor.The Gel Precursor includes hydrophilic monomer, crosslinking agent and initiator.
The hydrophilic monomer can be selected from 2- methacrylate (HEMA), N, N- dimethylacrylamide (DMA), methyl methacrylate (MMA), n-vinyl pyrrolidone (NVP), polyethylene glycol methacrylate-styrene polymer (PEGMA), Three (trimethyl silicon substrate) silane (TRIPS), dimethyl silicone polymer (PDMS), poly glycol ester (PEGMA), acrylic acid Hydroxyethyl ester (HEA), hydroxypropyl methacrylate (HPMA), dimethylaminoethyl methacrylate (DMAEMA) and third At least one of e pioic acid methyl ester (MA) etc..
The crosslinking agent can be selected from ethylene glycol dimethacrylate (EGDMA), trimethylol propane trimethyl acrylic acid At least one of ester (TMPTMA) and N, N'- methylene diacrylamine (MBAA) etc..
The initiator is thermal initiator.The thermal initiator can be selected from 2,2 '-azos two (2,4- methyl pentane nitrile), 2, 2 '-azos two (2- methyl propionitrile), 2,2 '-azos two (2- methylbutyronitrile), 2,2 '-azodiisobutyronitriles (AIBN) and peroxide At least one of compound (such as benzoyl peroxide).
Step 3, it is mixed to obtain one to mix the photochromic compound-cyclodextrin inclusion compound and the gel precursor Close object.
In the present embodiment, in the mixture, the mass percent of the hydrophilic monomer is 56%- 99.82%, the mass percent of the crosslinking agent is 0.03%-21.82%, and the mass percent of the initiator is 0.042%-18.62%, the mass percent of the photochromic compound-cyclodextrin inclusion compound are 0.08%-15.37%.
In the present embodiment, which can also further comprise a solvent.The solvent can be hydrophilic solvent.? In present embodiment, the solvent is the mixture of alcohol compound or alcohol compound and water, and more specifically, the solvent is Ethyl alcohol.
The mixture is placed in a mold and heats the mold by step 4, so that the Gel Precursor be made to occur Polymerization reaction and form a gel-in-matrix, and the photochromic compound-cyclodextrin inclusion compound is made to be scattered in the gel-in-matrix In, so that the photochromic ophthalmic lenses 100 be made.
In the present embodiment, the temperature of the heating is 60 degrees Celsius -90 degrees Celsius, and the time is -5 hours 0.5 hour.
Metering system when the cyclodextrin is the modified cyclodextrin after acrylic modified, on modified cyclodextrin Acid groups can generate covalent bond with each component reaction of the gel precursor, that is, the photochromic compound-cyclodextrin Inclusion compound can be by the covalently bonded together in the gel-in-matrix.
The present invention is specifically described below by embodiment.
Embodiment 1
The photochromic solution and 100L concentration for configuring the spiro-pyrans that 100L concentration is 0.01mol/L are 0.01mol/L's The two is mixed to form after inclusion compound and separates obtained photochromic compound-ring from mixed solution by cyclodextrin aqueous solution Cyclodextrin inclusion compound；Mixing HEMA, EGDMA, AIBN and the photochromic compound-cyclodextrin inclusion compound obtain mixture, The mass percent of HEMA, EGDMA, AIBN and the photochromic compound-cyclodextrin inclusion compound in the mixture Respectively 97.515%, 0.045%, 0.12% and 2.32%；The mixture is placed in mold to and is heated the mold, institute The temperature for stating heating is 70 degrees Celsius, and the time is 2 hours, so that the photochromic ophthalmic lenses 100 be made.
Embodiment 2
Configuring the spiral shell that 100L concentration is 0.01mol/L, the photochromic solution of pyridine and 100L concentration are 0.01mol/L's pah The two is mixed to form after inclusion compound and separates obtained photochromic compound-ring from mixed solution by cyclodextrin aqueous solution Cyclodextrin inclusion compound；Mix HEMA, NVP, TRIPS, EGDMA, AIBN, ethyl alcohol and the photochromic compound-cyclodextrin packet It closes object and obtains mixture, HEMA, NVP, TRIPS, EGDMA, AIBN, ethyl alcohol and the photochromic compound-cyclodextrin packet Close mass percent of the object in the mixture be respectively 9.18%, 23.12%, 31.21%, 0.045%, 0.12%, 31.085% and 5.24%；The mixture is placed in mold to and is heated the mold, the temperature of the heating is 65 Celsius Degree, the time is 4 hours, so that the photochromic ophthalmic lenses 100 be made.
Referring to Fig. 1, better embodiment of the present invention also provides a kind of photochromic ophthalmic as made from above-mentioned preparation method With eyeglass 100 comprising a gel-in-matrix 10 and the photochromic compound being scattered in the gel-in-matrix 10-cyclodextrin packet Close object 20.
In the present embodiment, the photochromic compound-cyclodextrin inclusion compound is in the photochromic ophthalmic lenses In mass percent be 0.08%-15.37%.
In addition, for those of ordinary skill in the art, can make in accordance with the technical idea of the present invention other each Kind changes and modifications, and all these changes and deformation all should belong to the protection scope of the claims in the present invention.

Claims (14)

1. a kind of preparation method of photochromic ophthalmic lenses, comprising:
One photochromic compound-cyclodextrin inclusion compound and a Gel Precursor, the photochromic compound-ring paste are provided Inclusion compounds are the cyclodextrin that envelope has photochromic compound；
Photochromic compound-the cyclodextrin inclusion compound and the gel precursor are mixed to obtain a mixture；And
The mixture is placed in a mold and heats the mold, to make the Gel Precursor generation polymerization reaction and shape At a gel-in-matrix, and it is scattered in the photochromic compound-cyclodextrin inclusion compound in the gel-in-matrix, so that institute be made State photochromic ophthalmic lenses.
2. the preparation method of photochromic ophthalmic lenses as described in claim 1, which is characterized in that the photochromic chemical combination Object is in spiro-pyrans, spiral shell pah pyridine, diarylethene, fulgide, hexa-aryl bi-imidazole, azobenzene and benzodihydropyran At least one.
3. the preparation method of photochromic ophthalmic lenses as described in claim 1, which is characterized in that the cyclodextrin is through first Modified cyclodextrin after base is acrylic acid modified.
4. the preparation method of photochromic ophthalmic lenses as described in claim 1, which is characterized in that the Gel Precursor includes Hydrophilic monomer, crosslinking agent and initiator.
5. the preparation method of photochromic ophthalmic lenses as claimed in claim 4, which is characterized in that the hydrophilic monomer choosing From 2- methacrylate, N, N- dimethylacrylamide, n-vinyl pyrrolidone, is gathered methyl methacrylate Glycolmethacrylate, three (trimethyl silicon substrate) silane, dimethyl silicone polymer, poly glycol ester, acrylic acid At least one in hydroxyethyl ester, hydroxypropyl methacrylate, dimethylaminoethyl methacrylate and methyl acrylate Kind.
6. the preparation method of photochromic ophthalmic lenses as claimed in claim 4, which is characterized in that the crosslinking agent is selected from second Diol dimethacrylate, trimethylol-propane trimethacrylate and N, in N'- methylene diacrylamine extremely Few one kind.
7. the preparation method of photochromic ophthalmic lenses as claimed in claim 4, which is characterized in that the initiator is selected from 2, 2 '-azos two (2,4- methyl pentane nitrile), 2,2 '-azos two (2- methyl propionitrile), 2,2 '-azos two (2- methylbutyronitrile), 2, At least one of 2 '-azodiisobutyronitriles and peroxide.
8. the preparation method of photochromic ophthalmic lenses as claimed in claim 4, which is characterized in that in the mixture, The mass percent of the hydrophilic monomer is 56%-99.82%, and the mass percent of the crosslinking agent is 0.03%- 21.82%, the mass percent of the initiator is 0.042%-18.62%, and the photochromic compound-is cyclodextrin encapsulated The mass percent of object is 0.08%-15.37%.
9. the preparation method of photochromic ophthalmic lenses as described in claim 1, which is characterized in that the mixture can also be into one Step includes a solvent, and the solvent is the mixture of alcohol compound or alcohol compound and water.
10. the preparation method of photochromic ophthalmic lenses as described in claim 1, which is characterized in that photochromicization Closing the preparation of object-cyclodextrin inclusion compound includes:
The photochromic compound is dissolved in one kind of ethyl alcohol, tetrahydrofuran and acetone and to form one photochromic molten Liquid, concentration of the photochromic compound in the photochromic solution are 0.0001mol/L-0.1mol/L；
The cyclodextrin is formed into a cyclodextrin aqueous solution in water, the cyclodextrin is in the cyclodextrin aqueous solution Concentration is 0.00001mol/L-0.1mol/L；
Above-mentioned photochromic solution and cyclodextrin aqueous solution are mixed to obtain a mixed solution, so that described in the cyclodextrin envelope Photochromic compound and form the photochromic compound-cyclodextrin inclusion compound；And
Photochromic compound-the cyclodextrin inclusion compound is separated from the mixed solution.
11. a kind of photochromic ophthalmic lenses, including an eye lens ontology, which is characterized in that the photochromic ophthalmically acceptable mirror Piece further includes the photochromic compound-cyclodextrin inclusion compound being scattered in the gel-in-matrix, the photochromic compound-ring Cyclodextrin inclusion compound is the cyclodextrin that envelope has photochromic compound.
12. photochromic ophthalmic lenses as claimed in claim 11, which is characterized in that the photochromic compound is selected from spiral shell Pyrans, spiral shell pah in pyridine, diarylethene, fulgide, hexa-aryl bi-imidazole, azobenzene and benzodihydropyran at least one Kind.
13. the preparation method of photochromic ophthalmic lenses as claimed in claim 11, which is characterized in that the cyclodextrin is warp Modified cyclodextrin after acrylic modified.
14. the preparation method of photochromic ophthalmic lenses as claimed in claim 11, which is characterized in that photochromicization Closing mass percent of the object-cyclodextrin inclusion compound in the photochromic ophthalmic lenses is 0.08%-15.37%.
CN201710724390.0A 2017-08-22 2017-08-22 Photochromic ophthalmic lenses and preparation method thereof Pending CN109422990A (en)

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Application Number Priority Date Filing Date Title
CN201710724390.0A CN109422990A (en) 2017-08-22 2017-08-22 Photochromic ophthalmic lenses and preparation method thereof

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110028323A (en) * 2019-03-08 2019-07-19 国装新材料技术(江苏)有限公司 Supermolecule ceramic forerunner based on cyclodextrin inclusion complex and preparation method thereof

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110028323A (en) * 2019-03-08 2019-07-19 国装新材料技术(江苏)有限公司 Supermolecule ceramic forerunner based on cyclodextrin inclusion complex and preparation method thereof

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