CN113968932B - Soft contact lenses and methods of making same - Google Patents

Soft contact lenses and methods of making same Download PDF

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Publication number
CN113968932B
CN113968932B CN202111237642.XA CN202111237642A CN113968932B CN 113968932 B CN113968932 B CN 113968932B CN 202111237642 A CN202111237642 A CN 202111237642A CN 113968932 B CN113968932 B CN 113968932B
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soft contact
contact lens
methacrylate
vitamin
heating
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CN113968932A (en
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李珈仪
李朝华
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Shenzhen Dashicheng Optical Technology Co ltd
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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
    • 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
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
    • 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
    • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/32—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals
    • C08F220/325—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals containing glycidyl radical, e.g. glycidyl (meth)acrylate
    • 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
    • C08F226/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
    • C08F226/06—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
    • C08F226/10—N-Vinyl-pyrrolidone
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/05—Alcohols; Metal alcoholates
    • 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

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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)
  • Physics & Mathematics (AREA)
  • Ophthalmology & Optometry (AREA)
  • General Health & Medical Sciences (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Eyeglasses (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

The invention discloses a soft contact lens and a preparation method thereof, wherein the soft contact lens comprises a thermal synthetic polymer, and the thermal synthetic polymer comprises the following raw materials: 2-hydroxyethyl methacrylate, glycerol methacrylate, ethylene glycol methacrylate and N-vinylpyrrolidone. According to the technical scheme, the thermally synthesized polymer comprises 2-hydroxyethyl methacrylate, glyceryl methacrylate, ethylene glycol methacrylate and N-vinyl pyrrolidone, and the thermally synthesized polymer has a high water content and can well relieve xerophthalmia by adding the four substances.

Description

Soft contact lenses and methods of making same
Technical Field
The invention relates to the technical field of contact lens production, in particular to a soft contact lens and a preparation method thereof.
Background
Contact lenses, also known as contact lenses, are lenses that are worn on the cornea of the eye to correct vision or protect the eye. It includes three kinds of hard, semi-hard and soft according to the hardness of the material.
Hard contact lenses hardly contain moisture due to insufficient oxygen permeability, and on the contrary, soft contact lenses contain moisture, can provide comfort for eyeballs, and are suitable for people of different age groups. However, wearing soft contact lenses is prone to bacterial growth, which can cause various problems with the cornea, such as: soft contact lenses generally cover a wider portion than the cornea, and the soft contact lenses are less movable, thereby causing insufficient space for circulation of tears, poor oxygen supply, excessive evaporation of tears or imbalance in tear components, and further causing damage to the surface of the eyeball or having a irritating feeling and a foreign body feeling. Therefore, in order to maintain a healthy eye state even when worn for a long time, it is necessary to study a soft contact lens that can alleviate xerophthalmia.
Currently, some soft contact lenses on the market alleviate xerophthalmia by adding 2-hydroxyethyl methacrylate (HEMA) monomer and a neutralizing agent, but this method has limited effect in alleviating or preventing xerophthalmia.
Disclosure of Invention
The invention mainly aims to provide a soft contact lens and a preparation method thereof, and aims to provide a soft contact lens capable of relieving xerophthalmia.
To achieve the above object, the present invention provides a soft contact lens comprising a thermally neutral synthetic polymer, the thermally neutral synthetic polymer comprising the following raw materials: 2-hydroxyethyl methacrylate, glycerol methacrylate, ethylene glycol methacrylate and N-vinylpyrrolidone.
Optionally, the thermally synthesized polymer comprises the following raw materials in parts by weight: 100 portions of 2-hydroxyethyl methacrylate, 0.1 to 5 portions of glycerol methacrylate, 0.1 to 5 portions of ethylene glycol methacrylate and 0.1 to 10 portions of N-vinyl pyrrolidone.
Optionally, the soft contact lens further comprises vitamin a.
Optionally, in the soft contact lens, the weight ratio of the vitamin a to the thermally synthetic polymer is (0.1 to 10): 100.
optionally, the vitamin a comprises at least one of polyethoxy retinoamide, retinoic acid, retinol, retinyl acetate, and retinyl palmitate.
The present invention also provides a method for producing a soft contact lens as described above, comprising the steps of:
s10, uniformly stirring and mixing 2-hydroxyethyl methacrylate, glyceryl methacrylate, ethylene glycol methacrylate and N-vinyl pyrrolidone to form a mixture;
and S20, injecting the mixture into a mold, heating and reacting to generate the soft contact lens.
Optionally, step S20 includes:
s201, injecting the mixture into a mold, heating at 70-90 ℃ for 70-90 min, and then heating at 90-110 ℃ for 10-30 min to obtain the soft contact lens.
Optionally, step S20 includes:
s202, injecting the mixture into a mold, heating at 70-90 ℃ for 70-90 min, then heating at 90-110 ℃ for 10-30 min, and then heating at 100-120 ℃ for 10-30 min to obtain the soft contact lens.
Optionally, in step S10, vitamin a is added after stirring and mixing, and mixing is performed uniformly.
According to the technical scheme, the thermally synthesized polymer comprises 2-hydroxyethyl methacrylate, glyceryl methacrylate, ethylene glycol methacrylate and N-vinyl pyrrolidone, and the thermally synthesized polymer has a high water content and can well relieve xerophthalmia by adding the four substances.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the embodiments or the prior art will be briefly described below, it is obvious that the drawings in the following description are only some embodiments of the present invention, and for those skilled in the art, other related drawings can be obtained according to the drawings without creative efforts.
FIG. 1 is a graph of light intensity absorbed at 300nm versus time for a solution in PBS according to one embodiment of a soft contact lens provided herein.
The implementation, functional features and advantages of the objects of the present invention will be further explained with reference to the accompanying drawings.
Detailed Description
The technical solutions in the embodiments of the present invention will be described clearly and completely below, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
In addition, if there is a description of "first", "second", etc. in an embodiment of the present invention, the description of "first", "second", etc. is for descriptive purposes only and is not to be construed as indicating or implying relative importance or implicitly indicating the number of technical features indicated. Thus, a feature defined as "first" or "second" may explicitly or implicitly include at least one such feature. In addition, the meaning of "and/or" appearing throughout includes three juxtapositions, exemplified by "A and/or B" including either A or B or both A and B. In addition, technical solutions between various embodiments may be combined with each other, but must be realized by a person skilled in the art, and when the technical solutions are contradictory or cannot be realized, such a combination should not be considered to exist, and is not within the protection scope of the present invention.
The wearing of soft contact lenses is prone to bacterial growth, which can cause various problems with the cornea, such as: soft contact lenses generally cover a wider area than the cornea, and the soft contact lenses are less movable, so that there is insufficient space for circulation of tears, oxygen is not smoothly supplied, and thus tears are excessively evaporated or the constituent components of tears are not uniform, thereby causing damage to the surface of the eyeball or having a stimulating feeling and a foreign body feeling. Therefore, in order to maintain a healthy eye state even when worn for a long time, it is necessary to study a soft contact lens that can alleviate xerophthalmia.
Currently, some soft contact lenses on the market alleviate xerophthalmia by adding 2-hydroxyethyl methacrylate (HEMA) monomer and a neutralizing agent, but this method has limited effect in alleviating or preventing xerophthalmia.
In view of the above, the present invention provides a soft contact lens, which can be a colorless or blue common lens, and can also be a colored cosmetic pupil lens. The soft contact lens comprises a thermally neutral synthetic polymer comprising the following raw materials: 2-hydroxyethyl methacrylate, glycerol methacrylate, ethylene glycol methacrylate and N-vinylpyrrolidone.
According to the technical scheme, the thermally synthesized polymer comprises 2-hydroxyethyl methacrylate, glycidyl Methacrylate (GMA), ethylene glycol methacrylate (EGDMA) and N-vinyl pyrrolidone (NVP), and the four substances are added, so that the thermally synthesized polymer has high water content in a single polymerization process, and can well relieve xerophthalmia.
Specifically, the hydroxyethyl 2-methacrylate has a structure represented by the following formula (1). Formula (1):
Figure BDA0003316255600000041
HEMA can be purchased on the market, has better stability on pH, temperature, osmotic pressure and the like, and has better water absorption property due to hydroxyl in a side chain, and the water content of the contact lens can be greatly improved to be more than 36wt% by adding HEMA.
The glycerol methacrylate has a structure represented by the following formula (2). Formula (2):
Figure BDA0003316255600000042
GMA is commercially available and by adding GMA, the stability of the polymer system can be increased and stabilized. When the weight ratio of GMA to HEMA is controlled to be in the range of 0.1-5.
The ethylene glycol methacrylate has a structure represented by the following formula (3). Formula (3):
Figure BDA0003316255600000051
EGDMA is commercially available and the stability of the polymer system can be further improved by the addition of EGDMA. However, the amount of EGDMA should not be too large, which would increase the hardness of the synthetic polymer in heat, decrease the stretchability, and decrease the water content, and therefore, the weight ratio of EGDMA to HEMA is preferably 0.1 to 5.
The N-vinylpyrrolidone has a structure represented by the following formula (4). Formula (4):
Figure BDA0003316255600000052
NVP is commercially available, and is added to increase the water content of soft contact lenses to 50-80 wt%, so that the wettability and oxygen permeability of the soft contact lenses are improved. When the weight ratio of NVP to HEMA is controlled within the range of 0.1-10.
Preferably, in some embodiments, the thermally synthesized polymer comprises the following parts by weight of the starting materials: 100 portions of 2-hydroxyethyl methacrylate, 0.1 to 5 portions of glycerol methacrylate, 0.1 to 5 portions of ethylene glycol methacrylate and 0.1 to 10 portions of N-vinyl pyrrolidone. When the four components are combined according to the specific proportion, the thermally-neutralized synthetic polymer with moderate hardness, high water content, good oxygen permeability and stable quality can be obtained.
In some embodiments, the soft contact lens further comprises vitamin a. The vitamin A is absorbed by the synthetic polymer in heat, so that the pharmacological effect of the vitamin A can be given to the lens, the effect of relieving xerophthalmia is further achieved, the synthetic polymer in heat can be slowly released in a body fluid environment after absorbing the vitamin A, the lens can have the effect of relieving xerophthalmia all the time during use, and in addition, the function of ultraviolet resistance can be given to the lens. Specifically, the soft contact lens (containing vitamin a) provided by the invention is put into a PBS solution similar to human body fluid, the solution is collected every hour, and the absorbance at 300nm of the solution is measured, and as a result, as shown in fig. 1, it can be seen from the figure that the content of the vitamin a in the solution is higher and higher along with the increase of time, that is, the vitamin a in the soft contact lens provided by the invention is released into the body fluid at a constant speed and slowly during the use period, so as to play a role in relieving eyeball dryness; in addition, the amount of light absorbed in 1 to 6 hours is controlled to 0.3 to 1.2, and the soft contact lens containing vitamin A also has an ultraviolet ray blocking function in terms of absorbing light in the ultraviolet ray region.
By using vitamin A with proper content, the effects of ultraviolet resistance and xerosis can be effectively realized, raw materials can be saved, and the quality of the lens can be ensured. Based on this, in some embodiments, the weight ratio of the vitamin a to the hot synthetic polymer in the soft contact lens is (0.1-10): 100.
wherein, the vitamin A can be any vitamin A material which can be directly purchased in the market. Preferably, in some embodiments, the vitamin a comprises at least one of polyethoxy retinoamide, retinoic acid, retinol, retinyl acetate, and retinyl palmitate.
The present invention also provides a method for producing a soft contact lens as described above, comprising the steps of:
and S10, uniformly stirring and mixing the 2-hydroxyethyl methacrylate, the glycerol methacrylate, the ethylene glycol methacrylate and the N-vinyl pyrrolidone to form a mixture.
Wherein the addition amount of each raw material component is as follows: 100 portions of 2-hydroxyethyl methacrylate, 0.1 to 5 portions of glycerol methacrylate, 0.1 to 5 portions of ethylene glycol methacrylate and 0.1 to 10 portions of N-vinyl pyrrolidone.
In addition, in some embodiments, the raw materials further include vitamin a, in this case, the vitamin a is added after being stirred and mixed uniformly, and the step S10 includes: stirring and uniformly mixing 2-hydroxyethyl methacrylate, glyceryl methacrylate, ethylene glycol methacrylate and N-vinyl pyrrolidone, adding vitamin A, and mixing to form a mixture.
Wherein the vitamin A comprises at least one of polyethoxy retinol, retinoic acid, retinol, retinyl acetate and retinyl palmitate; in the soft contact lens, the weight ratio of the vitamin A to the heat synthetic polymer is (0.1-10): 100.
and S20, injecting the mixture into a mold, heating to react, and generating the soft contact lens.
By baking at a specific temperature, the 2-hydroxyethyl methacrylate, the glycerol methacrylate, the ethylene glycol methacrylate and the N-vinyl pyrrolidone can be reacted to generate a thermally synthesized polymer. In some embodiments, step S20 may be implemented as follows:
step S201, injecting the mixture into a mold, heating at 70-90 ℃ for 70-90 min, and then heating at 90-110 ℃ for 10-30 min to obtain the soft contact lens.
In other embodiments, step S20 may also operate as follows:
s202, injecting the mixture into a mold, heating at 70-90 ℃ for 70-90 min, then heating at 90-110 ℃ for 10-30 min, and then heating at 100-120 ℃ for 10-30 min to obtain the soft contact lens.
The preparation method of the soft contact lens is simple and convenient and is convenient to operate.
The technical solutions of the present invention are further described in detail with reference to specific examples, which should be understood that the following examples are only illustrative and not limiting.
Example 1
The raw material formula comprises: 100 parts of 2-hydroxyethyl methacrylate, 1 part of glycerol methacrylate, 1 part of ethylene glycol methacrylate, 1 part of N-vinyl pyrrolidone and 1.5 parts of vitamin A.
The preparation method comprises the following steps:
the components are weighed according to the formula for later use. Uniformly stirring and mixing 2-hydroxyethyl methacrylate, glycerol methacrylate, ethylene glycol methacrylate and N-vinyl pyrrolidone, adding vitamin A, and mixing to form a mixture.
Injecting the mixture into a mold, heating at 80 deg.C for 80min, and further heating at 100 deg.C for 20min to obtain soft contact lens.
Example 2
Except that the formula of the raw materials is adjusted to 100 parts of 2-hydroxyethyl methacrylate, 0.1 part of glycerol methacrylate, 0.1 part of ethylene glycol methacrylate, 0.1 part of N-vinyl pyrrolidone and 0.1 part of vitamin A; the vitamin A was the same as in example 1 except that it was polyethoxy retinoamide.
Example 3
Except that the formula of the raw materials is adjusted to 100 parts of 2-hydroxyethyl methacrylate, 5 parts of glycerol methacrylate, 5 parts of ethylene glycol methacrylate, 10 parts of N-vinyl pyrrolidone and 12 parts of vitamin A; vitamin A is the same as in example 1 except that it includes a mixture of retinoic acid and retinol.
Example 4
Except that the formula of the raw materials is adjusted to 100 parts of 2-hydroxyethyl methacrylate, 2 parts of glycerol methacrylate, 1 part of ethylene glycol methacrylate, 1 part of N-vinyl pyrrolidone and 5 parts of vitamin A; vitamin a was the same as in example 1 except that it included a mixture of retinol, retinyl acetate, and retinyl palmitate.
Example 5
Except that the formula of the raw materials is adjusted to 100 parts of 2-hydroxyethyl methacrylate, 1 part of glycerol methacrylate, 2 parts of ethylene glycol methacrylate, 0.1 part of N-vinyl pyrrolidone and 2 parts of vitamin A; vitamin A includes retinyl palmitate "and is otherwise the same as in example 1.
Example 6
Except that the formula of the raw materials is adjusted to 100 parts of 2-hydroxyethyl methacrylate, 0.8 part of glycerol methacrylate, 2 parts of ethylene glycol methacrylate, 5 parts of N-vinyl pyrrolidone and 2 parts of vitamin A; vitamin A was the same as in example 1 except that it included polyethoxy retinoamide ".
Example 7
The raw material formulation was the same as in example 1.
The preparation method comprises the following steps:
weighing the components according to the formula for later use. Uniformly stirring and mixing 2-hydroxyethyl methacrylate, glycerol methacrylate, ethylene glycol methacrylate and N-vinyl pyrrolidone, adding vitamin A, and mixing to form a mixture.
The mixture was injected into a mold and heated at 70 ℃ for 70min and then at 110 ℃ for 10min to obtain soft contact lenses.
Example 8
The raw material formulation was the same as in example 1.
The preparation method comprises the following steps:
the components are weighed according to the formula for later use. Uniformly stirring and mixing 2-hydroxyethyl methacrylate, glycerol methacrylate, ethylene glycol methacrylate and N-vinyl pyrrolidone, adding vitamin A, and mixing to form a mixture.
Injecting the mixture into a mold, heating at 90 deg.C for 90min, and further heating at 90 deg.C for 10min to obtain soft contact lens.
Example 9
The raw material formulation was the same as in example 3.
The preparation method comprises the following steps:
weighing the components according to the formula for later use. Stirring and uniformly mixing 2-hydroxyethyl methacrylate, glyceryl methacrylate, ethylene glycol methacrylate and N-vinyl pyrrolidone, adding vitamin A, and mixing to form a mixture.
Injecting the mixture into a mold, heating at 80 deg.C for 80min, further heating at 100 deg.C for 20min, and then heating at 110 deg.C for 20min to obtain soft contact lens.
The above description is only a preferred embodiment of the present invention, and is not intended to limit the scope of the present invention, and all equivalent structural changes made by using the content of the present specification or other related technical fields within the spirit of the present invention are included in the scope of the present invention.

Claims (6)

1. A soft contact lens comprising a thermally neutral synthetic polymer, said thermally neutral synthetic polymer comprising the following raw materials: 2-hydroxyethyl methacrylate, glycerol methacrylate, ethylene glycol methacrylate and N-vinyl pyrrolidone;
wherein 100 parts of 2-hydroxyethyl methacrylate, 0.1-5 parts of glycerol methacrylate, 0.1-5 parts of ethylene glycol methacrylate and 0.1-10 parts of N-vinyl pyrrolidone; the soft contact lens further comprises vitamin a; the weight ratio of the vitamin A to the heat synthetic polymer is (0.1-10): 100.
2. the soft contact lens of claim 1, wherein the vitamin a comprises at least one of polyethoxy retinoamide, retinoic acid, retinol, retinyl acetate, and retinyl palmitate.
3. A method of manufacturing a soft contact lens as claimed in any one of claims 1 to 2, comprising the steps of:
s10, uniformly stirring and mixing 2-hydroxyethyl methacrylate, glycerol methacrylate, ethylene glycol methacrylate and N-vinyl pyrrolidone to form a mixture;
and S20, injecting the mixture into a mold, heating and reacting to generate the soft contact lens.
4. A method of making a soft contact lens as in claim 3, wherein step S20 comprises:
s201, injecting the mixture into a mold, heating at 70-90 ℃ for 70-90 min, and then heating at 90-110 ℃ for 10-30 min to obtain the soft contact lens.
5. A method of making a soft contact lens as in claim 3, wherein step S20 comprises:
s202, injecting the mixture into a mold, heating at 70-90 ℃ for 70-90 min, then heating at 90-110 ℃ for 10-30 min, and then heating at 100-120 ℃ for 10-30 min to obtain the soft contact lens.
6. A method for producing a soft contact lens as claimed in claim 3, wherein in step S10, vitamin a is added after the mixing and stirring, and the mixing is performed uniformly.
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