CN113004528A - Contact lens and surfactant for contact lens - Google Patents
Contact lens and surfactant for contact lens Download PDFInfo
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- CN113004528A CN113004528A CN202010366355.8A CN202010366355A CN113004528A CN 113004528 A CN113004528 A CN 113004528A CN 202010366355 A CN202010366355 A CN 202010366355A CN 113004528 A CN113004528 A CN 113004528A
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- surfactant
- lens
- contact lens
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- 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
- C08G77/46—Block-or graft-polymers containing polysiloxane sequences containing polyether sequences
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
- G02B1/041—Lenses
- G02B1/043—Contact lenses
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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 discloses a surfactant for contact lenses, which has the following structural formula:
wherein k and l are integers, k is 10-20, l is 10-20, X is-OH, -COOH, -NH2，–NH，–CO–NH2R，–CO–NHRR'，–(O–CH2‑CH2)nOr- (O-CH)2–CH(CH3)–)n–(O–CH2–CH2)mM and n are integers, m is 5-10, n is 5-10, R is H, CH3Or CH2COOR ', R' is a hydrocarbon group having not more than 20 carbon atoms, R1Is C1-C6 alkyl; the surfactant of the present invention is a siloxane copolymer (molecular weight 10)000-20,000 Da), has excellent Si-O-Si chain flexibility, and is easy to control morphology.
Description
Technical Field
The invention relates to the technical field of contact lenses, in particular to a contact lens and a surfactant for the contact lens.
Background
The tear layer of existing corneal contact lenses is not sufficiently fluid and tear exchange is not maximally utilized. The lacrimal fluid layer contains countless antibodies and nutrients, which are vital to the maintenance of the cornea health. In general, contact lenses are clinically administered to maintain corneal tissue integrity and health by maximizing the tear layer formed between the lens and the cornea. Although the conventional contact lenses mainly comprising silicon have high oxygen permeability, the chemical properties of the contact lenses are water repellency, but the corneal tissue is hydrophilic, so that the conventional similar products lack the utilization of the flow of a lacrimal fluid layer, cause insufficient comfort and are contradictory to physiological metabolism.
Disclosure of Invention
To solve the problems mentioned in the background above, the present invention provides a contact lens and a surfactant for use in the contact lens.
In order to achieve the purpose, the invention adopts the following technical scheme:
in a first aspect of the invention, there is provided a surfactant for use in a contact lens having the formula:
wherein k and l are integers, k is 10-20, l is 10-20, X is a hydrophilic group in a single or oligomeric form, and R is a hydrophilic group in a single or oligomeric form1Is C1-C6 alkyl, cyclohexyl or phenyl, R is H, CH3Or CH2COOR ', R' is a hydrocarbon group having not more than 20 carbon atoms.
Wherein X is selected from-OH, -COOH, -NH2，–NH，–CO–NH2R，–CO–NHRR'，–(O–CH2-CH2)nOr- (O-CH)2–CH(CH3)–)n–(O–CH2–CH2)mWherein m and n are integers, m is 5-10, n is 5-10, R is H, CH3Or CH2COOR ', R' is a hydrocarbon group having not more than 20 carbon atoms.
Wherein the molecular weight of the surfactant is 10,000-20,000 Da.
In a second aspect of the present invention, a contact lens is provided, which comprises the following raw materials: the above-mentioned surfactant.
Wherein the mass dosage range of the surfactant is 3-5%.
Compared with the prior art, the invention has the following beneficial effects: the surfactant is a siloxane copolymer, is prepared from a siloxane skeleton and hydrophilic branched chains (such as ethylene oxide), has excellent Si-O-Si chain flexibility, and is easy to control the form, so that the hydrophilic groups of the surfactant are easy to expose on the surface of a lens when the surfactant is self-assembled, and the hydrophobic groups are folded into a spiral central core to be used as an oxygen transmission channel to increase the permeability of oxygen in a contact lens; the surfactant is added into the contact lens, so that the surface tension gradient of the contact lens can be promoted, water molecules in a capillary channel below the contact lens are driven by the surface tension gradient through the Gibbs-Marangoni effect convection principle, the sufficient exchange of tears on the corneal surface below the lens is promoted, and the physiological metabolism speed of corneal cells is improved; the surfactants of the present invention are added to contact lenses in place of the modified siloxane oligomers commonly used today, resulting in higher performance and lower cost contact lenses.
Drawings
The invention is described in further detail below with reference to the following figures and detailed description:
FIG. 1 is a schematic diagram of the operation of the surfactant of the present invention;
FIG. 2 is a schematic representation of capillary convection phenomena in the sub-lens tear layer of the surfactants of the present invention;
FIG. 3 is a graph showing the trend of oxygen permeability (Dk) as the silicone surfactant content increases in the contact lenses of the invention.
Detailed Description
The following description of the embodiments of the present invention is provided for illustrative purposes, and other advantages and effects of the present invention will become apparent to those skilled in the art from the present disclosure.
Example one
A surfactant for use in a contact lens, having the formula:
wherein k and l are integers, k is 10-20, l is 10-20, X is a hydrophilic group in a single or oligomeric form, and R is a hydrophilic group in a single or oligomeric form1Is C1-C6 alkyl, cyclohexyl or phenyl, R is H, CH3Or CH2COOR ', R' is a hydrocarbon group having not more than 20 carbon atoms.
Preferably, X is selected from-OH, -COOH, -NH2，–NH，–CO–NH2R，–CO–NHRR'，–(O–CH2-CH2)nOr- (O-CH)2–CH(CH3)–)n–(O–CH2–CH2)mWherein m and n are integers, m is 5-10, n is 5-10, R is H, CH3Or CH2COOR ', R' is a hydrocarbon group having not more than 20 carbon atoms.
The surfactant comprises a siloxane skeleton and a hydrophilic branch chain (such as ethylene oxide), has excellent Si-O-Si chain flexibility, and is easy to conform to form control.
The preparation method of the surfactant comprises the following steps:
45 g of methylhydrogensiloxane-dimethylsiloxane copolymer having a molecular weight of 8500-9500 and 27 g of an allyl poly (ene/propylene oxide) (PEG-PPG) copolymer having a molecular weight of about 850 (the PEG/PPG ratio is 1: 1) were subjected to hydrosilylation in a three-neck round-bottom flask. Speier catalyst used (H)2PtCl6) The concentration was 40ppm and the reaction temperature was maintained at 65 ℃. After 2 hours, 1.4 grams of charcoal was added at room temperature and the solution was stirred for 2 hours. After filtration, the solvent was evaporated under vacuum at 60 ℃ for 24 hours to give the product, surfactant 1.
trimethylsiloxy-terminated methylhydrogensiloxane dimethylsiloxane copolymer having a molecular weight of 5500-6500 (available from Gelest Inc.) 11 g was hydrosilylated in a three-neck round bottom flask with Allyl polyethylene glycol (Allyl PEG) copolymer having a molecular weight of about 1500 (Tiwan Surfactants Inc.) 3.3 g. Karstedt's catalyst, purchased from Sigma-Aldrich, was added to the solution to give a final concentration of 30ppm of platinum in the reaction mixture. The flask was heated and refluxed at 70 ℃ with slow stirring for 1 hour. The resultant product was then placed on a vacuum line for 24 hours to remove the solvent, thus synthesizing surfactant 4.
Example two
(1) Preparation of lens 1: lens 1 was prepared with the following HCL24 formulation, with the following percentages by mass.
HCL24 formulation: 43% 3-tris (trimethylsiloxy) silylpropylmethacrylate; 23% trifluoroethyl methacrylate; 12.5% methacrylic acid; 12.5% of methyl methacrylate; 5% ethylene glycol dimethacrylate; 3.65% of 1, 3-bis (3-methacryloxypropyl) tetrakis- (trimethylsiloxy) disiloxane; 0.35% 2, 2' -azobis (isobutyronitrile), or Irgacure 819(BASF) was used as photoinitiator.
Copolymerization is carried out by adopting the formula, and a copolymerization mixture is injected into a mold made of two pieces of oleophobic glass, wherein the two pieces of oleophobic glass are separated by a polytetrafluoroethylene separator. The mold was placed in a nitrogen-filled chamber and then exposed to 365mm ultraviolet light (UV9W-2, Lightning Enterprises, limigton, ME) for 5-10 minutes; the mould is then heated in an oven at 70 ℃ for 24-48 hours and then at a temperature of 90 ℃ for 24-36 hours. The resulting rods were then cut into buttons about 3-4 mm thick, and then cut into lenses. The lenses were made for oxygen transmission and contact angle testing.
(2) Preparation of lens 2: lens 2 was prepared by adding 3% by weight of surfactant 1 to the above HCL24 formulation and reducing the 3-tris (trimethylsiloxy) silylpropylmethacrylate formulation accordingly.
(3) Preparation of lens 3: lens 3 was prepared with the following GP formulation.
GP formula: 56% 3-tris (trimethylsiloxy) silylpropylmethacrylate; 25% trifluoroethyl methacrylate; 2% methacrylic acid; 7% of methyl methacrylate; 4% ethylene glycol dimethacrylate; 5.65% of 1, 3-bis (3-methacryloxypropyl) tetrakis- (trimethylsiloxy) disiloxane; 0.35% 2, 2' -azobis (isobutyronitrile) as thermal polymerization initiator or Irgacure 819(BASF) as photoinitiator.
The process for the preparation of lens 3 is carried out in the same manner as lens 1.
(4) Preparation of lens 4: to the GP formulation, 5% (mass percent) surfactant 4 was added and the 3-tris (trimethylsiloxy) silylpropylmethacrylate ratio was decreased accordingly to produce lens 4.
The surface tension gradient measurements of the lens center and the lens edge were performed on lens 1, lens 2, lens 3, and lens 4, respectively, and the measurement results are shown in table 1.
TABLE 1
Wherein, because the center of the lens contacts with the eyeball, the temperature is close to the body temperature in use, so the surface tension gradient test temperature of the center of the lens is 36 ℃. And the lens edge was in contact with air, the surface tension gradient test temperature was 20 c at room temperature. The difference in surface tension gradient is the difference between the surface tension gradient at the center of the lens and at the edge of the lens, and this temperature induced gradient difference causes natural convection of the tear layer.
As shown in table 1, the addition of surfactant 1 and surfactant 4 in HCL24 and GP both increased the surface tension and increased the gradient difference between the center and edge of the lens, which facilitated tear flow and increased tear exchange rate.
FIG. 2 is a schematic diagram of capillary convection phenomena in the tear layer under the lens, where γ represents the surface tension of the lens, and since γ is high at the edge and low at the center, the movement of water molecules on the surface of the lens from the low γ to the high γ region will drive the adjacent boundary layer to generate convection flow. In the figure, 100 μm is the lens height, and 7-10 μm is the tear thickness.
EXAMPLE III
As can be seen from FIG. 3, as the amount of surfactant 2 was increased, the oxygen transmission rate (Dk) of the resulting contact lens increased, and HCL24 showed a greater Dk dependence than GP due to the higher methyl acrylate content of HCL24, the added surfactantThe agent increases O due to enhanced penetration of oxygen molecules in methyl acrylate2Permeability throughout the material.
The addition of the surfactant 2 increases the oxygen permeability of the obtained lens, and the working principle is shown in figure 1. The surfactant added to the lens self-assembles in the tear layer, wherein the hydrophilic groups of the surfactant are exposed at the lens surface and fold the hydrophobic groups into a central core of a helix, forming a helically folded oxygen transport channel, facilitating the transport of oxygen.
It should be understood that the structures, ratios, sizes, and the like shown in the drawings and described in the specification are only used for matching with the disclosure of the specification, so as to be understood and read by those skilled in the art, and are not used to limit the conditions under which the present invention can be implemented, so that the present invention has no technical significance, and any structural modification, ratio relationship change, or size adjustment should still fall within the scope of the present invention without affecting the efficacy and the achievable purpose of the present invention. In addition, the terms "upper", "lower", "left", "right", "middle" and "one" used in the present specification are for clarity of description, and are not intended to limit the scope of the present invention, and the relative relationship between the terms and the terms is not to be construed as a scope of the present invention.
The foregoing embodiments are merely illustrative of the principles and utilities of the present invention and are not intended to limit the invention. Any person skilled in the art can modify or change the above-mentioned embodiments without departing from the spirit and scope of the present invention. Accordingly, it is intended that all equivalent modifications or changes which can be made by those skilled in the art without departing from the spirit and technical spirit of the present invention be covered by the claims of the present invention.
Claims (5)
1. A surfactant for use in a contact lens, characterized by the formula:
wherein k and l are integers, k is 10-20, l is 10-20, X is a hydrophilic group in a single or oligomeric form, and R is a hydrophilic group in a single or oligomeric form1Is C1-C6 alkyl, cyclohexyl or phenyl, R is H, CH3Or CH2COOR ', R' is a hydrocarbon group having not more than 20 carbon atoms.
2. The surfactant for use in a contact lens of claim 1, wherein X is selected from the group consisting of-OH, -COOH, -NH2，–NH，–CO–NH2R，–CO–NHRR'，–(O–CH2-CH2)nOr- (O-CH)2–CH(CH3)–)n–(O–CH2–CH2)mWherein m and n are integers, m is 5-10, n is 5-10, R is H, CH3Or CH2COOR ', R' is a hydrocarbon group having not more than 20 carbon atoms.
3. The surfactant for use in a contact lens of claim 1, wherein said surfactant has a molecular weight of 10,000 to 20,000 Da.
4. A contact lens, comprising the following raw materials: a surfactant as claimed in any one of claims 1 to 3.
5. The contact lens of claim 4, wherein the surfactant is present in an amount ranging from 3% to 5% by mass.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2019113279769 | 2019-12-20 | ||
| CN201911327976 | 2019-12-20 |
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| Publication Number | Publication Date |
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| CN113004528A true CN113004528A (en) | 2021-06-22 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN202010366355.8A Pending CN113004528A (en) | 2019-12-20 | 2020-04-30 | Contact lens and surfactant for contact lens |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101932632A (en) * | 2008-02-08 | 2010-12-29 | 旭化成爱美株式会社 | Hydrophilic polysiloxane macromonomer, and production and use of the same |
| CN102323629A (en) * | 2004-08-27 | 2012-01-18 | 库柏维景国际控股公司 | Silicone hydrogel contact lens |
| US20150240092A1 (en) * | 2012-08-22 | 2015-08-27 | Zhijun Wang | Surface Control Additive For Radiation Curing System, Preparation Method Therefor And Application Thereof |
| CN109867808A (en) * | 2018-12-24 | 2019-06-11 | 南京美思德新材料有限公司 | A kind of high rebound foam organic silicon surfactant and preparation method |
-
2020
- 2020-04-30 CN CN202010366355.8A patent/CN113004528A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102323629A (en) * | 2004-08-27 | 2012-01-18 | 库柏维景国际控股公司 | Silicone hydrogel contact lens |
| CN101932632A (en) * | 2008-02-08 | 2010-12-29 | 旭化成爱美株式会社 | Hydrophilic polysiloxane macromonomer, and production and use of the same |
| US20150240092A1 (en) * | 2012-08-22 | 2015-08-27 | Zhijun Wang | Surface Control Additive For Radiation Curing System, Preparation Method Therefor And Application Thereof |
| CN109867808A (en) * | 2018-12-24 | 2019-06-11 | 南京美思德新材料有限公司 | A kind of high rebound foam organic silicon surfactant and preparation method |
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