CN101096451A - Novel material for contact lens and synthesizing method thereof - Google Patents
Novel material for contact lens and synthesizing method thereof Download PDFInfo
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- CN101096451A CN101096451A CNA2007100248577A CN200710024857A CN101096451A CN 101096451 A CN101096451 A CN 101096451A CN A2007100248577 A CNA2007100248577 A CN A2007100248577A CN 200710024857 A CN200710024857 A CN 200710024857A CN 101096451 A CN101096451 A CN 101096451A
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- polyglutamic acid
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- contact lens
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Abstract
The invention discloses a new material of contact lens and synthesizing method with structural formula as follows (n is 2-3000; m is 2-4X104), which comprises the following steps: dissolving gamma-polyglutamic acid into water; adding fitful crosslinking agent; stirring evenly; adjusting pH value to 3.5-7.0 to react under 30-100 deg. c for 28-100h; fetching the product to adsorb water sufficiently. The invention has simple synthesizing path, strong operatable property and good biological compatibility, which possesses larger social and economic benefit.
Description
Technical field
The invention belongs to field of new, relate to novel material for contact lens and synthetic method thereof.
Background technology
China wears contact lens, and the person accounts for about 3% (U.S., Japan and other countries account for 10%) of total population, continuous progress and improvement along with production technique and material, this population ratio has the trend of continuous rising, it is reported, China soft lens market increased by 10%, 2003 year in 2002 and then increases by 14%.And because contact lens belong to consumption class daily necessities, so its market demand is undoubtedly huge.
Since the hard mirror of first plastics forties in 20th century came out, contact lens were developed rapidly.According to the difference of hardness, usually contact lens are divided into hard mirror and soft lens two portions:
1, hard mirror Development of Materials stage and characteristics
| Developmental stage | Advantage | Shortcoming |
| Polymethylmethacrylate (PMMA) | Transmittance height, antisolvent precipitation, stable performance, be easy to processing | Oxygen-permeable is lower; Just wear uncomfortable |
| Cellulose acetate butyrate (CAB) | Oxygen permeability is better than PMMA slightly, and is durable | Be easy to warpage after the suction |
| Siloxanes | Oxygen permeability is good | Wettability is poor especially, is easy to adsorb the lipid throw out |
| Siloxanes/alkylmethacrylate polymer (SMA) | Eyeglass is transparent, stable, oxygen-permeable is good, have good hardness | Influence stability, wearing quality and the wettability of eyeglass |
2, soft lens Development of Materials stage and characteristics
| Developmental stage | Advantage | Shortcoming |
| Poly hydroxy ethyl acrylate (PHEMA) | Soft, good springiness | Oxygen-permeable is relatively poor |
| Non-HEMA material (as: multipolymer of MMA and NVP) | Higher modulus of elasticity and tensile strength | Water content is low slightly |
| Biomimetic material (as: biomimetic material of phosphoryl choline derivative) | Eyeglass is preserved moisture, antisolvent precipitation | The time of wearing is short |
| Hydrogel material | High-moisture, softness | Oxygen-permeable, thermostability are poor slightly |
In sum, contact lenses material aspect also exists following defective:
(1) oxygen permeability of hydrogel material and its water content are linear, in order to improve the oxygen transmission rate of contact lenses, must improve its water content.But, improve the strength degradation that water content causes hydrogel, need to increase the thickness of contact lenses material, and cause the decline of oxygen transmission rate like this.
(2) raising of hydrogel water content causes protein and lipoid in the tear to deposit on contact lenses easily, not only contact lenses is polluted, and also can influence its printing opacity homogeneity, causes bacteria breed.
(3) the high hydrogel material of water content also dewaters in wearing process easily.After the dehydration, the transmittance of contact lenses and printing opacity homogeneity descend, and capture the moisture on the cornea.
Therefore, the research direction of hydrogel class contact lenses material when being to guarantee that the contact lenses material has higher moisture and oxygen flow ability, improves its intensity and moisture retention.
(γ-PGA) water-absorbing resin is a kind of biodegradable macromolecular material with tridimensional network to gamma-polyglutamic acid-, and is nontoxic, has better biocompatibility, thermostability, moisture retention, environmental friendliness.Its range of application is wide, given play to big effect (Shih I day by day in fields such as agricultural, gardening, medicine, medical treatment, oil, chemical, daily necessities, environmental protection, building materials, food, Yah Y.The production of poly-(γ-glutanmic acid) frommicroorganisms and its various applications.Bioresource Technology.2001,79:207-225).If the change reaction conditions, the degree of depth is crosslinked, and this resin will be expected to become the novel material of contact lens, yet there are no report both at home and abroad, is worth and using value so this is studied very high theory.
Summary of the invention
The objective of the invention is to overcome the deficiency of above-mentioned traditional eyewear, provide a kind of high-moisture percentage, high transmission rate, good biocompatibility, moisture retention good, the high-permeability contact lens material that human body is had no side effect.
Another object of the present invention provides the synthetic method of above-mentioned contact lens material.
The present invention is with gamma-polyglutamic acid-(γ-Polyglutamic Acid, abbreviation γ-PGA) adopt chemical crosslink technique to make super-high molecular weight gamma-polyglutamic acid (being called for short HMPGA) also as novel material for contact lens.
The objective of the invention is to realize by following technical measures:
A kind of contact lens material, its structural formula is as follows:
Wherein: n is 2～3000, and m is 2～4 * 10
4
This material prepares by following method:
Gamma-polyglutamic acid-is dissolved in the water, adds proper amount of cross-linking agent, stir, regulating pH is 3.5～7.0, and 30～100 ℃ of reactions 28～100 hours, reaction product was taken out abundant suction and got final product.
Described contact lens material, wherein the molecular weight of gamma-polyglutamic acid-is 2～5,000,000 dalton.
Described contact lens material, wherein linking agent is polyethyleneglycol diglycidylether, glycol ether glycidyl ether or diglycidyl ether of ethylene glycol.The molecular weight polyethylene glycol that adopts in the polyethyleneglycol diglycidylether can be 200～3000 dalton.
Described contact lens material, wherein the consumption of gamma-polyglutamic acid-, water and linking agent is: γ-PGA monomer and H
2The mol ratio of O is 1: 19～1: 100, and the monomeric mol ratio of linking agent and γ-PGA is 1: 5～1: 25.
The synthetic method of described contact lens material, this method is that gamma-polyglutamic acid-is dissolved in the water, and adds proper amount of cross-linking agent, stirs, and regulating pH is 3.5～7.0, and 30～100 ℃ of reactions 28～100 hours, reaction product was taken out abundant suction and is got final product.
Described synthetic method, wherein the molecular weight of gamma-polyglutamic acid-is 2～5,000,000 dalton.
Described synthetic method, wherein linking agent is polyethyleneglycol diglycidylether, glycol ether glycidyl ether or diglycidyl ether of ethylene glycol.The molecular weight polyethylene glycol that adopts in the polyethyleneglycol diglycidylether can be 200～3000 dalton.
Described synthetic method is characterized in that the consumption of gamma-polyglutamic acid-, water and linking agent is: γ-PGA monomer and H
2The mol ratio of O is 1: 19～1: 100; The monomeric mol ratio of linking agent and γ-PGA is 1: 5～1: 25.
Below the present invention is elaborated:
With the gamma-polyglutamic acid-is raw material, uses water as solvent, adds proper amount of cross-linking agent (as diglycidyl ether of ethylene glycol, glycol ether glycidyl ether or polyethyleneglycol diglycidylether), according to mol ratio γ-PGA (monomer): H
2O=1: 19～1: 100; Linking agent: γ-PGA (monomer)=fed intake in 1: 25～1: 5 at 30 ℃～90 ℃, reacted 28～100 hours under pH=3.5～7.0 conditions, and reaction is shown in (II)
Beneficial effect of the present invention:
Synthetic route provided by the invention is simple, workable, the product good biocompatibility, human body is had no side effect, has high-moisture percentage (water absorbent rate reaches 220g/g), average transmittance is 98%, the DSC curve shows that this material has good thermostability in the human body temperature scope, can be used as the application of novel material for contact lens, has bigger social benefit and economic benefit.
Embodiment
The invention will be further elaborated by the following examples.
Embodiment 1:
Getting the 2g gamma-polyglutamic acid-is dissolved in the 6g distilled water, add the 2.4g diglycidyl ether of ethylene glycol, stir, the pH value to 4.3 of sodium hydroxide conditioned reaction thing with 10%, then, the reaction 35h time immerses product in the water in 70 ℃ thermostat water bath, take out behind the 24h, the product water absorbent rate is that 220g/g, average transmittance are 98%.
Embodiment 2:
Getting the 2g gamma-polyglutamic acid-is dissolved in the 14g distilled water, add 1.8g glycol ether glycidyl ether, stir, the pH value to 3.8 of sodium hydroxide conditioned reaction thing with 10%, then, the reaction 50h time immerses product in the water in 50 ℃ thermostat water bath, take out behind the 24h, the product water absorbent rate is that 340g/g, average transmittance are 64%.
Embodiment 3:
Getting the 2g gamma-polyglutamic acid-is dissolved in the 30g distilled water, add 3.2g polyethyleneglycol diglycidylether (molecular weight of polyethyleneglycol diglycidylether is 800), stir, the pH value to 7.0 of sodium hydroxide conditioned reaction thing with 10%, then, the reaction 45h time immerses product in the water in 100 ℃ thermostat water bath, take out behind the 24h, the product water absorbent rate is that 490g/g, average transmittance are 53%.
Embodiment 4～15: synthetic parameters and effect see Table 1.
Table 1:HMPGA synthesis condition is to the influence of water absorbent rate, transmittance
| Sequence number | The linking agent title | Proportioning (mol ratio) | The pH value | Temperature of reaction (℃) | Reaction times (h) | Water absorbent rate (g/g) | Transmittance | |
| γ-PGA monomer/H 2O | Linking agent/γ-PGA monomer | |||||||
| 4 | Diglycidyl ether of ethylene glycol | 1∶24 | 1∶8 | 4.3 | 60 | 30 | 600 | 82％ |
| 5 | 1∶22 | 1∶5 | 4.3 | 70 | 35 | 240 | 90％ | |
| 6 | 1∶20 | 1∶6 | 3.8 | 80 | 40 | 210 | 43％ | |
| 7 | 1∶22 | 1∶6 | 4.3 | 70 | 35 | 220 | 99％ | |
| 8 | The glycol ether glycidyl ether | 1∶100 | 1∶20 | 6.0 | 40 | 35 | 740 | 21％ |
| 9 | 1∶75 | 1∶13 | 5.0 | 60 | 45 | 1020 | 51％ | |
| 10 | 1∶50 | 1∶10 | 4.0 | 80 | 55 | 1120 | 60％ | |
| 11 | 1∶25 | 1∶7 | 3.5 | 90 | 65 | 560 | 70％ | |
| 12 | Polyethylene Glycol Bisglycidyl Ether (300) | 1∶24 | 1∶8 | 4.3 | 60 | 30 | 600 | 82％ |
| 13 | 1∶22 | 1∶5 | 4.3 | 70 | 35 | 240 | 90％ | |
| 14 | 1∶20 | 1∶6 | 3.8 | 80 | 40 | 210 | 43％ | |
| 15 | 1∶22 | 1∶6 | 4.3 | 70 | 35 | 220 | 99％ | |
| 16 | Polyethylene Glycol Bisglycidyl Ether (1000) | 1∶100 | 1∶25 | 7.0 | 30 | 28 | 560 | 19％ |
| 17 | 1∶50 | 1∶15 | 5.5 | 50 | 50 | 870 | 55％ | |
| 18 | 1∶30 | 1∶10 | 4.5 | 70 | 70 | 900 | 38％ | |
| 19 | Polyethylene Glycol Bisglycidyl Ether (1500) | 1∶19 | 1∶5 | 3.5 | 90 | 100 | 700 | 24％ |
| 20 | 1∶30 | 1∶10 | 4.5 | 70 | 70 | 900 | 38％ | |
| 21 | 1∶20 | 1∶6 | 3.8 | 80 | 40 | 210 | 43％ | |
| 22 | Polyethylene Glycol Bisglycidyl Ether (2500) | 1∶22 | 1∶6 | 4.3 | 70 | 35 | 220 | 99％ |
| 23 | 1∶24 | 1∶8 | 4.3 | 60 | 30 | 600 | 82％ | |
| 24 | 1∶100 | 1∶25 | 7.0 | 30 | 28 | 560 | 19％ | |
Claims (8)
1. contact lens material is characterized in that its structural formula is as follows:
Wherein: n is 2～3000, and m is 2～4 * 10
4
This material prepares by following method:
Gamma-polyglutamic acid-is dissolved in the water, adds proper amount of cross-linking agent, stir, regulating pH is 3.5～7.0, and 30～100 ℃ of reactions 28～100 hours, reaction product was taken out abundant suction and got final product.
2, contact lens material according to claim 1, the molecular weight that it is characterized in that gamma-polyglutamic acid-is 2～5,000,000.
3, contact lens material according to claim 1 is characterized in that linking agent is polyethyleneglycol diglycidylether, glycol ether glycidyl ether or diglycidyl ether of ethylene glycol.
4, contact lens material according to claim 1 is characterized in that the consumption of gamma-polyglutamic acid-, water and linking agent is: gamma-polyglutamic acid-monomer and H
2The mol ratio of O is 1: 19～1: 100, and the monomeric mol ratio of linking agent and gamma-polyglutamic acid-is 1: 5～1: 25.
5, the synthetic method of contact lens material as claimed in claim 1, it is characterized in that this method is that the r-polyglutamic acid is dissolved in the water, add proper amount of cross-linking agent, stir, regulating pH is 3.5～7.0,30～100 ℃ of reactions 28～100 hours, reaction product was taken out fully to absorb water and is got final product.
6, synthetic method according to claim 5, the molecular weight that it is characterized in that the r-polyglutamic acid is 2～5,000,000.
7, synthetic method according to claim 5 is characterized in that linking agent is polyethyleneglycol diglycidylether, glycol ether glycidyl ether or diglycidyl ether of ethylene glycol.
8, synthetic method according to claim 5 is characterized in that the consumption of gamma-polyglutamic acid-, water and linking agent is: gamma-polyglutamic acid-monomer and H
2The mol ratio of O is 1: 19～1: 100, and the monomeric mol ratio of linking agent and gamma-polyglutamic acid-is 1: 5～1: 25.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2007100248577A CN101096451A (en) | 2007-07-05 | 2007-07-05 | Novel material for contact lens and synthesizing method thereof |
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|---|---|---|---|
| CNA2007100248577A CN101096451A (en) | 2007-07-05 | 2007-07-05 | Novel material for contact lens and synthesizing method thereof |
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| CN101096451A true CN101096451A (en) | 2008-01-02 |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102816326A (en) * | 2012-08-15 | 2012-12-12 | 中科院广州化学有限公司 | Polyglutamic acid macromolecule cross-linking agent containing carbon-carbon double bonds, preparation method and application thereof |
| WO2015017191A1 (en) * | 2013-08-02 | 2015-02-05 | Bausch & Lomb Incorporated | Hydrogel monomer mix containing added water |
| CN105462247A (en) * | 2014-09-12 | 2016-04-06 | 季叶俊 | Poly glutamic acid contact lens material and preparation method thereof |
| CN105917270A (en) * | 2013-11-15 | 2016-08-31 | 视觉力学有限责任公司 | Contact lens with a hydrophilic layer |
| US10525170B2 (en) | 2014-12-09 | 2020-01-07 | Tangible Science, Llc | Medical device coating with a biocompatible layer |
| US11181754B2 (en) | 2012-08-27 | 2021-11-23 | Tangible Science, Llc | Contact lens with a hydrophilic layer |
| TWI798452B (en) * | 2019-06-17 | 2023-04-11 | 晶碩光學股份有限公司 | Contact lens product |
-
2007
- 2007-07-05 CN CNA2007100248577A patent/CN101096451A/en active Pending
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102816326A (en) * | 2012-08-15 | 2012-12-12 | 中科院广州化学有限公司 | Polyglutamic acid macromolecule cross-linking agent containing carbon-carbon double bonds, preparation method and application thereof |
| CN102816326B (en) * | 2012-08-15 | 2014-01-15 | 中科院广州化学有限公司 | Polyglutamic acid macromolecule cross-linking agent containing carbon-carbon double bonds, preparation method and application thereof |
| US11181754B2 (en) | 2012-08-27 | 2021-11-23 | Tangible Science, Llc | Contact lens with a hydrophilic layer |
| WO2015017191A1 (en) * | 2013-08-02 | 2015-02-05 | Bausch & Lomb Incorporated | Hydrogel monomer mix containing added water |
| US9389336B2 (en) | 2013-08-02 | 2016-07-12 | Bausch & Lomb Incorporated | Hydrogel monomer mix containing added water |
| CN105917270A (en) * | 2013-11-15 | 2016-08-31 | 视觉力学有限责任公司 | Contact lens with a hydrophilic layer |
| US11433628B2 (en) | 2013-11-15 | 2022-09-06 | Tangible Science, Inc. | Contact lens with a hydrophilic layer |
| CN105462247A (en) * | 2014-09-12 | 2016-04-06 | 季叶俊 | Poly glutamic acid contact lens material and preparation method thereof |
| US10525170B2 (en) | 2014-12-09 | 2020-01-07 | Tangible Science, Llc | Medical device coating with a biocompatible layer |
| US11260150B2 (en) | 2014-12-09 | 2022-03-01 | Tangible Science, Inc. | Medical device coating with a biocompatible layer |
| TWI798452B (en) * | 2019-06-17 | 2023-04-11 | 晶碩光學股份有限公司 | Contact lens product |
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