CN114790263A - Material for manufacturing contact lenses and contact lenses made of same - Google Patents
Material for manufacturing contact lenses and contact lenses made of same Download PDFInfo
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- CN114790263A CN114790263A CN202110105874.3A CN202110105874A CN114790263A CN 114790263 A CN114790263 A CN 114790263A CN 202110105874 A CN202110105874 A CN 202110105874A CN 114790263 A CN114790263 A CN 114790263A
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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
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/12—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polysiloxanes
- C08F283/124—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polysiloxanes on to polysiloxanes having carbon-to-carbon double bonds
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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
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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
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- Health & Medical Sciences (AREA)
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Abstract
The present invention relates to materials for making contact lenses and contact lenses made therefrom. The material for making contact lenses includes a first component, a second component, at least one hydrophilic monomer, and at least one photoinitiator. The first component and the second component are respectively expressed by the following formula (1) and the following formula (2), wherein Z1 is a first silica gel monomer, n11 to 1.5, o1 between 1 and 2, Z2 is a second silicone rubber monomer, n2 between 1 and 5, o2 between 1 and 2.
Description
Technical Field
The present invention relates to a material for manufacturing contact lenses and contact lenses thereof, and more particularly, to a silicone-containing material for manufacturing contact lenses and contact lenses thereof.
Background
Silica hydrogel (silica hydrogel) is the main material currently on the market for manufacturing soft contact lenses, and combines the high oxygen permeability of "silica" and the hydrophilicity of "hydrogel", so that oxygen can directly pass through the lens to contact with the cornea to maintain sufficient oxygen content, and the lens has high water content to improve the comfort, therefore, the silica hydrogel contact lenses can reduce the uncomfortable symptoms caused by oxygen deficiency of the cornea or water deficiency of the eyes, and further prolong the wearing time of users.
However, to further enhance comfort, many manufacturers and research teams modify the composition and structure of the silicone gel to further optimize the oxygen permeability and water content of the contact lens. For example, european patent publication No. EP2443484B1 discloses a silicone hydrogel comprised of (a) one or more siloxane-containing homopolymers and (B) one or more biomedical device-forming monomers, wherein the homopolymers may be urethane monomers and the monomers are hydrophilic monomers selected from the group consisting of methacrylic acid, acrylic acid, hydroxyethyl 2-methacrylate, hydroxyethyl 2-acrylate, N-vinylpyrrolidone, N-vinylcaprolactone, methacrylamide, N-dimethylacrylamide, ethylene glycol dimethacrylate and mixtures thereof. Further, U.S. Pat. No. US 9464159B 2 discloses a contact lens consisting of (a) at least one polyol of formula (I), (B) at least one diisocyanate or polyisocyanate, and (c) at least one OH-terminal chain extender. In addition, U.S. patent publication No. US20180340036A, U.S. patent publication No. US10676575B2, U.S. patent publication No. US9708450B2, etc. also disclose other improved structural compositions of silicone adhesives.
However, the existing silicone hydrogel contact lenses still have the problems of insufficient oxygen content and water content under the condition of maintaining the necessary mechanical properties. Therefore, how to manufacture contact lenses capable of improving wearing comfort and maintaining necessary mechanical properties at the same time is a major issue to be solved in the art.
Disclosure of Invention
An object of the present invention is to solve the problem of insufficient oxygen and water content of known silicone hydrogel contact lenses.
To achieve the above object, the present invention provides a material for manufacturing a contact lens, comprising:
a first component represented by the following formula (1),
wherein Z1 is a first silicone rubber monomer, n1 is between 1 and 1.5, and o1 is between 1 and 2;
a second component represented by the following formula (2),
wherein Z2 is a second silicone rubber monomer, n2 is between 1 and 5, and o2 is between 1 and 2;
at least one hydrophilic monomer; and
at least one photoinitiator.
In one embodiment, wherein the first silicone gum monomer Z1 is represented by the following formula (4),
wherein m1 is between 1 and 3.
In one embodiment, wherein the second silicone rubber monomer Z2 is represented by the following formula (5),
wherein m2 is between 1 and 3.
In one embodiment, the method further comprises:
a third component represented by the following formula (3),
wherein Z3 is a third silicone rubber monomer, n3 is between 4 and 6, and o3 is between 4 and 5.
In one embodiment, the third silicone rubber monomer Z3 is represented by formula (6);
wherein m3 is 1.
In one embodiment, the hydrophilic monomer includes at least one of the group consisting of 2-hydroxyethyl methacrylate, N-vinylpyrrolidone, methacrylic acid and N, N-dimethylacrylamide, or a combination thereof.
In one embodiment, the solvent further comprises isopropyl alcohol.
In one embodiment, the adhesive further comprises a cross-linking agent, wherein the cross-linking agent is trimethylolpropane trimethacrylate.
The invention also provides a contact lens which is made of the material.
The present invention further provides a material for manufacturing a contact lens, comprising:
a first component represented by the following formula (1);
wherein Z1 is a first silicone rubber monomer, n1 is between 1 and 1.5, and o1 is between 1 and 2;
a third component represented by the following formula (3),
wherein Z3 is a third silicone rubber monomer, n3 is between 4 and 6, o3 is between 4 and 5;
at least one hydrophilic monomer; and
at least one photoinitiator.
In one embodiment, the first silicone gum monomer Z1 is represented by formula (4) below;
wherein m1 is between 1 and 3.
In one embodiment, the third silicone rubber monomer Z3 is represented by formula (6);
wherein m3 is 1.
In one embodiment, the method further comprises:
a second component represented by the following formula (2),
wherein Z2 is a second silicone rubber monomer, n2 is between 1 and 5, and o2 is between 1 and 2.
In one embodiment, the second silicone rubber monomer Z2 is represented by the following formula (5);
wherein m2 is between 1 and 3.
In one embodiment, the hydrophilic monomer comprises 2-hydroxyethyl methacrylate, N-vinylpyrrolidone, methacrylic acid, N-dimethylacrylamide, or a mixture or combination of any of the foregoing.
In one embodiment, the solvent further comprises isopropyl alcohol.
In one embodiment, the adhesive further comprises a cross-linking agent, wherein the cross-linking agent is trimethylolpropane trimethacrylate.
The invention further provides a contact lens made of the material.
Detailed Description
As used herein, the term "first component" refers to a silicon-containing monomeric structural unit represented by the following formula (1):
wherein Z1 is a first silicone rubber monomer, n1 is between 1 and 1.5, and o1 is between 1 and 2.
In one embodiment, o1 is 1, i.e., the "first component" is a silicon-containing monomeric structural unit represented by the formula:
in one embodiment, the "first component" further refers to a silicon-containing monomer structural unit represented by the following formula (1'):
as used herein, the term "second component" refers to a silicon-containing monomer structural unit represented by the following formula (2):
wherein Z2 is a second silicone rubber monomer, n2 is between 1 and 5, and o2 is between 1 and 2.
In one embodiment, o2 is 1, i.e., the "second component" is a silicon-containing monomeric structural unit represented by the formula:
in one embodiment, the "second component" further refers to a silicon-containing monomer structural unit represented by the following formula (2'):
as used herein, the term "third component" refers to a structural unit represented by the following formula (3):
wherein Z3 is a third silicone rubber monomer, n3 is between 4 and 6, and o3 is between 4 and 5.
In one embodiment, o3 is 1, i.e., the "third component" is a silicon-containing monomeric structural unit represented by the formula:
in one embodiment, the "third component" further refers to a silicon-containing monomer structural unit represented by the following formula (3'):
the n1, o1, n2, o2, n3 and o3 can be integers or non-integers.
The invention provides a material for manufacturing a contact lens, according to one embodiment, the material comprises a first component, a second component, at least one hydrophilic monomer and at least one photoinitiator; according to another embodiment, the material comprises a first component, a third component, at least one hydrophilic monomer and at least one photoinitiator; according to another embodiment, the material includes a first component, a second component, a third component, at least one hydrophilic monomer, and at least one photoinitiator.
In one embodiment, the first silicone gum monomer Z1 is represented by the following formula (4):
wherein m1 is between 1 and 3.
In one embodiment, the second silicone gum monomer Z2 is represented by the following formula (5):
wherein m2 is between 1 and 3.
The m1 and m2 may be integers or non-integers.
In one embodiment, the third silicone gum monomer Z3 is represented by the following formula (6):
wherein m3 is 1.
The hydrophilic monomer has at least one functional group with a polymerizable double bond and at least one functional group with hydrophilicity, wherein the functional group with the polymerizable double bond is a monomer containing acrylic acid or vinyl. In one embodiment, the hydrophilic monomer includes at least one of the group consisting of 2-hydroxyethyl methacrylate (HEMA), N-vinyl pyrrolidone (NVP), methacrylic acid (MAA), and N, N-Dimethylacrylamide (DMA), or a combination thereof; the photoinitiator may be any initiator that is excited by light (e.g., ultraviolet light) to chemically chain the first component, the second component, and/or the third component with the hydrophilic monomer. In one embodiment, the photoinitiator may be used
1173 (2-Hydroxy-2-methyl-1-phenyl-1-propanone) or
819 (phenylbis (2,4,6-trimethylbenzoyl) phosphine oxide (phenyl bis (2,4,6-trimethylbenzoyl) -phosphine oxide)).
In one embodiment, the material further comprises a solvent, which may be isopropyl alcohol (IPA), and a crosslinking agent, which may be trimethylolpropane trimethacrylate (TMPTMA).
In one embodiment, the weight average molecular weight (Mw) of formula (1) is between 1700 and 2100, and the molecular weight distribution (Mw/Mn) is between 1.5 and 2.0; formula (2) has a weight average molecular weight (Mw) between 3000 and 4560 and a molecular weight distribution (Mw/Mn) between 1.5 and 2.0; formula (3) has a weight average molecular weight (Mw) of between 2246 and 3219 and a molecular weight distribution (Mw/Mn) of between 1.5 and 2.0.
In one embodiment, the material for manufacturing the contact lens comprises formula (1), formula (2) and/or formula (3), and an additive, wherein the weight percentage of formula (1) (i.e., the first component) is between 35 wt.% and 50 wt.%, the weight percentage of formula (2) (i.e., the second component) is between 0 wt.% and 20 wt.%, the weight percentage of formula (3) (i.e., the third component) is between 0 wt.% and 20 wt.%, and the weight percentage of the additive is between 15 wt.% and 35 wt.%. The additive includes the sum of the hydrophilic monomer, the photoinitiator, the solvent and the cross-linking agent.
The oxygen permeability (Dk) of the contact lens prepared by the material can be between 70 and 115, the water content can be between 30 and 45 percent, and the Young modulus can be between 0.2 and 1.2.
The following preparation examples are provided to illustrate the synthesis of silicon-containing monomer-containing silica gels of the present invention of the formula (1), formula (2) and formula (3).
Examples
[ PREPARATION EXAMPLE 1 ]
In a three-necked flask, 80mL of Tetrahydrofuran (THF), 40g of α - [3- [1,3,3, 3-tetramethyl-1- (trimethylsilyl-oxo) disiloxane ] -propyl- ω -hydroxypolyoxyethylene (monomerobinol terminated polydisiloxane), 13.69g of ε -Caprolactone (ε -Caproalactone) and 0.0040g of dibutyltin dilaurate were added and mixed to form a solution A. The solution A was stirred at 120 ℃ for 6 hours to perform ring-opening polymerization (ROP), and after the reaction, the reactant was washed with pure water and subjected to dehydration and filtration treatment to obtain an intermediate represented by the following formula (1a) and having a weight-average molecular weight (Mw) of 1200.
m1 is between 1 and 3, n1 is between 1 and 1.5.
Further, the intermediate was mixed with 2.52g of isophorone diisocyanate (IPDI), reacted at 45 ℃ for 5 hours, and 0.0025g of dibutyltin dilaurate (dibutyl tin dilaurate) was further added dropwise to form a solution B. Subsequently, 1.48g of 2-hydroxyethyl methacrylate (HEMA) and 0.0015g of dibutyltin dilaurate (dibutyl tin dilaurate) were added dropwise to the solution B and reacted at 45 ℃ for 3 hours.
Finally, Tetrahydrofuran (THF) in the solution B was removed by evaporation to obtain a product represented by the following formula (1B) having a weight average molecular weight (Mw) of 1800.
m1 is between 1 and 3, n1 is between 1 and 1.5, and o1 is between 1 and 2.
[ PREPARATION EXAMPLE 2 ]
In a three-necked flask, 100mL of Tetrahydrofuran (THF), 50g of α - [3- [1,3,3, 3-tetramethyl-1- (trimethylsilyl-oxo) disiloxane ] -propyl- ω -hydroxypolyoxyethylene (monocarbinol terminated polydimethysiloxane), 5.8g of ε -Caprolactone (ε -Caprolactone) and 0.0040g of dibutyltin dilaurate were added and mixed to form a solution C. The solution C was stirred at 120 ℃ for 6 hours to effect ring-opening polymerization. After the reaction, the reaction product was washed with pure water and subjected to dehydration and filtration treatment to obtain an intermediate represented by the following formula (2a) and having a weight average molecular weight (Mw) of 3018.
n2 is between 1 and 5, and m2 is between 1 and 3.
Further, the intermediate was mixed with 11.12g of isophorone diisocyanate (IPDI) and reacted at 45 ℃ for 5 hours, and 0.001g of dibutyltin dilaurate (dibutyl tin dilaurate) was further added dropwise to form a solution D. Subsequently, 6.6g of 2-hydroxyethyl methacrylate (HEMA) and 0.006g of dibutyltin dilaurate were added dropwise to the solution D and reacted at 45 ℃ for 3 hours.
The Tetrahydrofuran (THF) in the solution D was finally removed by evaporation to obtain a product represented by the following formula (2b) having a weight average molecular weight (Mw) of 3760.
m2 is between 1 and 3, n2 is between 1 and 5, and o2 is between 1 and 2.
[ PREPARATION EXAMPLE 3 ]
120mL of Tetrahydrofuran (THF), 54.4g of tetrakis (2-hydroxyethoxy) silane (tetrakis (2-hydroxyethoxy) silane), 91.32g of ε -Caprolactone (ε -Caproalactone) and 0.0054g of dibutyltin dilaurate were added to a three-necked flask to mix to obtain a solution E, and the solution E was stirred at 120 ℃ for 6 hours to perform ring-opening polymerization. After the reaction, the reaction mixture was washed with a large amount of water and dehydrated and filtered to obtain an intermediate of the following formula (3a) having a weight average molecular weight (Mw) of 738.
m3 is 1, n3 is between 4 and 6.
Further, the intermediate was mixed with 117.84g of isophorone diisocyanate (IPDI) and reacted at 45 ℃ for 5 hours, and 0.017g of dibutyltin dilaurate (dibutyl tin dilaurate) was further added dropwise to form a solution F. Then, 104.12g of 2-hydroxyethyl methacrylate (HEMA) and 0.014g of dibutyltin dilaurate (dibutyl tin dilaurate) were dropped into the solution F and reacted at 45 ℃ for 3 hours. The Tetrahydrofuran (THF) in the solution F was finally removed by evaporation to obtain a product represented by the following formula (3b) having a weight average molecular weight (Mw) of 2575.
m3 is 1, n3 is between 4 and 6, and o3 is between 4 and 5.
Table 1 below is an experimental example prepared from the materials disclosed herein to illustrate the specific efficacy of the contact lenses of the present invention. The formula (1), the formula (2) and the formula (3) are the silicon hydrogel components, HEMA, NVP, MAA and DMA are hydrophilic monomers,
is a photo initiator, IPA is a solvent, and TMPTMA is a cross-linking agent. In addition, the unit of table 1 is weight (g).
TABLE 1
The materials of the above experimental examples were mixed at 55mW/m 2 The ultraviolet light of (2) for 100 seconds to cure the lens, thereby forming a contact lens. And tests of oxygen permeability, water content and Young's modulus were performed for these experimental examples 1 to 4, and the test results are shown in Table 2 below, in which the oxygen permeability, water content and Young's modulus were measured according to the industry ISO standards.
TABLE 2
| Experimental example 1 | Experimental example 2 | Experimental example 3 | Experimental example 4 | |
| Oxygen permeability (Dk) | 84 | 70 | 100 | 115 |
| Water content ratio | 45％ | 32％ | 43％ | 40％ |
| Young's modulus | 0.7 | 1.2 | 0.2 | 0.4 |
As can be seen from Table 2, contact lenses made from the materials disclosed herein have high oxygen transmission rates (Dk) ranging from 70 to 115, high water contents ranging from 30% to 45%, and low Young's modulus ranging from 0.2 to 1.2. When a user wears the contact lens, more oxygen contacts the cornea and maintains the moisture of eyes, and meanwhile, the foreign body sensation of the contact lens touching the eyes is reduced, so that the wearing comfort is improved, and the wearing time can be prolonged.
Claims (14)
1. A material for use in the manufacture of contact lenses, comprising:
a first component represented by the following formula (1),
wherein Z1 is a first silicone rubber monomer, n1 is between 1 and 1.5, and o1 is between 1 and 2;
a second component represented by the following formula (2),
wherein Z2 is a second silicone rubber monomer, n2 is between 1 and 5, and o2 is between 1 and 2;
at least one hydrophilic monomer; and
at least one photoinitiator.
2. The material of claim 1, wherein the first silicone gum monomer Z1 is represented by formula (4),
wherein m1 is between 1 and 3.
3. The material of claim 1, wherein the second silicone gum monomer Z2 is represented by the following formula (5),
wherein m2 is between 1 and 3.
4. The material of claim 1, further comprising:
a third component represented by the following formula (3),
wherein n3 is between 4 and 6, o3 is between 4 and 5, and Z3 is a third silica gel monomer represented by the following formula (6);
wherein m3 is 1.
5. The material of claim 1, wherein the hydrophilic monomer comprises at least one of the group consisting of 2-hydroxyethyl methacrylate, N-vinyl pyrrolidone, methacrylic acid, and N, N-dimethylacrylamide, or a combination thereof.
6. The material of claim 1, further comprising a solvent that is isopropyl alcohol and a cross-linking agent that is trimethylolpropane trimethacrylate.
7. A contact lens made from the material of any one of claims 1 to 6.
8. A material for use in the manufacture of contact lenses, comprising:
a first component represented by the following formula (1);
wherein Z1 is a first silicone rubber monomer, n1 is between 1 and 1.5, and o1 is between 1 and 2;
a third component represented by the following formula (3),
wherein Z3 is a third silicone rubber monomer, n3 is between 4 and 6, and o3 is between 4 and 5;
at least one hydrophilic monomer; and
at least one photoinitiator.
9. The material of claim 8, wherein the first silicone monomer Z1 is represented by formula (4);
wherein m1 is between 1 and 3.
10. The material of claim 8, wherein the third silicone gum monomer Z3 is represented by formula (6);
wherein m3 is 1.
11. The material of claim 8, further comprising:
a second component represented by the following formula (2),
wherein n2 is between 1 and 5, o2 is between 1 and 2, and Z2 is a second silica gel monomer represented by formula (5);
wherein m2 is between 1 and 3.
12. The material of claim 8, wherein the hydrophilic monomer comprises 2-hydroxyethyl methacrylate, N-vinyl pyrrolidone, methacrylic acid, N-dimethylacrylamide, or a combination thereof.
13. The material of claim 8, further comprising a solvent that is isopropanol and a crosslinking agent that is trimethylolpropane trimethacrylate.
14. A contact lens made from the material of any one of claims 8 to 13.
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| Application Number | Priority Date | Filing Date | Title |
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| CN202110105874.3A CN114790263A (en) | 2021-01-26 | 2021-01-26 | Material for manufacturing contact lenses and contact lenses made of same |
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| Application Number | Priority Date | Filing Date | Title |
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| CN202110105874.3A CN114790263A (en) | 2021-01-26 | 2021-01-26 | Material for manufacturing contact lenses and contact lenses made of same |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101948409A (en) * | 2010-08-04 | 2011-01-19 | 辽宁恒星精细化工有限公司 | Hydroxyethyl methacrylate-modified isophorone diisocyanate and preparation method thereof |
| CN103224596A (en) * | 2013-03-18 | 2013-07-31 | 明基材料有限公司 | Contact lens material, contact lens and manufacturing method of contact lens |
| TW201346375A (en) * | 2012-05-11 | 2013-11-16 | Benq Materials Corp | Method for forming contact lenses and contact lenses therefrom |
| CN112048052A (en) * | 2019-06-06 | 2020-12-08 | 亮点光学股份有限公司 | High oxygen permeation and high oxygen permeation hydrophilic polymer material |
-
2021
- 2021-01-26 CN CN202110105874.3A patent/CN114790263A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101948409A (en) * | 2010-08-04 | 2011-01-19 | 辽宁恒星精细化工有限公司 | Hydroxyethyl methacrylate-modified isophorone diisocyanate and preparation method thereof |
| TW201346375A (en) * | 2012-05-11 | 2013-11-16 | Benq Materials Corp | Method for forming contact lenses and contact lenses therefrom |
| CN103224596A (en) * | 2013-03-18 | 2013-07-31 | 明基材料有限公司 | Contact lens material, contact lens and manufacturing method of contact lens |
| CN112048052A (en) * | 2019-06-06 | 2020-12-08 | 亮点光学股份有限公司 | High oxygen permeation and high oxygen permeation hydrophilic polymer material |
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