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CN116338979A - Blue light filtering ophthalmic lens - Google Patents

Blue light filtering ophthalmic lens Download PDF

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Publication number
CN116338979A
CN116338979A CN202111600598.4A CN202111600598A CN116338979A CN 116338979 A CN116338979 A CN 116338979A CN 202111600598 A CN202111600598 A CN 202111600598A CN 116338979 A CN116338979 A CN 116338979A
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ophthalmic lens
linear
blue light
blue
substrate
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陈冠宏
曹郁涵
李年加
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Yongsheng Optics Co ltd
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Yongsheng Optics Co ltd
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    • GPHYSICS
    • G02OPTICS
    • G02CSPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
    • G02C7/00Optical parts
    • G02C7/02Lenses; Lens systems ; Methods of designing lenses
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00Use of organic ingredients
    • C08K5/16Nitrogen-containing compounds
    • C08K5/34Heterocyclic compounds having nitrogen in the ring
    • C08K5/3467Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
    • C08K5/3472Five-membered rings
    • C08K5/3475Five-membered rings condensed with carbocyclic rings
    • GPHYSICS
    • G02OPTICS
    • G02BOPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
    • G02B1/041Lenses
    • GPHYSICS
    • G02OPTICS
    • G02BOPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
    • G02B1/041Lenses
    • G02B1/043Contact lenses
    • GPHYSICS
    • G02OPTICS
    • G02BOPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00Optical elements other than lenses
    • G02B5/20Filters
    • GPHYSICS
    • G02OPTICS
    • G02CSPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
    • G02C7/00Optical parts
    • G02C7/02Lenses; Lens systems ; Methods of designing lenses
    • G02C7/04Contact lenses for the eyes

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  • Physics & Mathematics (AREA)
  • Health & Medical Sciences (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Ophthalmology & Optometry (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
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Abstract

The invention discloses a blue light filtering ophthalmic lens, which has a db value less than 2, the ophthalmic lens comprises a blue light filtering compound and a substrate, wherein db = (b #) 1 –(b*) 0 This (b) 1 B is the value of b for the ophthalmic lens, and the (b) 0 Is the b-value of a control lens.

Description

Blue light filtering ophthalmic lens
Technical Field
The present invention relates to an ophthalmic lens for filtering blue light, and more particularly, to an ophthalmic lens for filtering blue light which is not yellowish or colorless and transparent.
Background
With the rapid development of technology, the relationship between electronic products and people is also becoming more and more intimate, and the relationship has taken a very important position in daily life. However, most display parts of electronic products, such as liquid crystal display screens, mobile phone screens, etc., need to have a full color rendering degree in the visible light band to make the products more acceptable to consumers, so that the above products mostly emit a large amount of blue light.
Blue light or blue light generally refers to light having a wavelength between 380nm and 460nm, which has a higher energy in the visible. When the electronic product is used, blue light can penetrate through human eyes to reach retina, and long-term irradiation of the retina can cause the attenuation of pigment epithelial cells, so that vision is damaged. Therefore, if the user uses the electronic products to make eyes receive blue light for a long time, irreversible damage can be caused to the eyes.
In order to reduce or avoid damage to the human eye caused by blue light, many lenses or products for filtering blue light, such as blue-light protection glasses, blue-light filtering protection films, etc., are commercially available. A conventional blue light filter lens is mostly manufactured by adding a substance having a blue light filtering property to a base material of the lens so as to block blue light from directly irradiating eyes of a user. However, the blue light filtering material is usually used for filtering blue light in visible light, and meanwhile, the lens is in a yellowish appearance, so that the product is not good in sales, and the purchase will of consumers is reduced.
Disclosure of Invention
An object of the present invention is to provide an ophthalmic lens for blue light filtration that is not yellowish or colorless transparent.
In order to achieve the above-mentioned objective, the present invention provides an ophthalmic lens for filtering blue light, which has a db value less than 2, the ophthalmic lens comprising a blue light filtering compound and a substrate, wherein db= (b) 1 –(b*) 0 This (b) 1 B is the value of b for the ophthalmic lens, and the (b) 0 Is the b-value of a control lens.
In order to achieve the above objective, the present invention provides an ophthalmic lens for filtering blue light, having a db value less than 2 and a blue blocking ratio between 10 and 60%, the ophthalmic lens comprising a blue light filtering compound and a substrate, wherein db= (b:) 1 –(b*) 0 This (b) 1 B is the value of b for the ophthalmic lens, and the (b) 0 Is the b-value of a control lens.
The b values are the values of the blue-yellow coordinate axes of the lens in the CIELAB color space.
In some embodiments of the invention, the blue-filtering compound is present in an amount of 0.4 to 10%,1 to 10%, or 5 to 10% by weight.
According to the present invention, an ophthalmic lens as described above may have a thickness of 0.04 to 2.00mm, or a thickness of 0.04 to 1.80mm, or a thickness of 0.04 to 1.50 mm.
In order to achieve the above-mentioned objective, the present invention provides an ophthalmic lens for filtering blue light, wherein the thickness of the ophthalmic lens is between 0.04 and 1.5mm, the blue light blocking rate of the ophthalmic lens is between 10 and 60%, and the ophthalmic lens comprises a substrate and a blue light filtering compound having the structural formula (a):
Figure BDA0003432985590000021
wherein R1 is hydrogen, a C1 to C10 linear or branched alkyl, a C6 to C15 aralkyl, -R2-X, -O-R2-X, or-N-R2-X; wherein R2 is a C1 to C10 linear or branched alkylene group, a hydroxyl-substituted C1 to C10 linear or branched alkylene group, or a C1 to C10 linear or branched alkylene group interrupted by an ester group, X is-OH, -OC (O) R3, -NH2, -NC (O) R3, -NCO, -COOH, or-COOR 3; wherein R3 is a C1 to C10 linear or branched alkyl group, or a C3 to C10 linear or branched alkenyl group.
In some embodiments of the invention, the blue-filtering compound is present in an amount of 0.4 to 10% by weight.
In order to achieve the above object, the present invention provides an ophthalmic lens for filtering blue light, which is prepared by a method comprising the steps of: mixing a blue light filtering compound and a substrate to obtain a mixed solution, wherein the weight percentage of the blue light filtering compound is 0.4 to 10.0 percent, and the weight percentage of the substrate is 90.0 to 99.6 percent; adding the mixed solution into a forming die; and causing a polymerization reaction of the mixed solution in the forming mold to obtain the ophthalmic lens, wherein the ophthalmic lens has a db value less than or equal to 2, wherein db= (b) 1 –(b*) 0 This (b) 1 B is the value of b for the ophthalmic lens, and the (b) 0 Is one ofB values for control lenses.
In order to achieve the above object, the present invention provides an ophthalmic lens for filtering blue light, which is prepared by a method comprising the steps of: mixing a blue light filtering compound and a substrate to obtain a mixed solution, wherein the weight percentage of the blue light filtering compound is 0.4 to 10.0 percent, and the weight percentage of the substrate is 90.0 to 99.6 percent; adding the mixed solution into a forming die; and causing a polymerization reaction of the mixed solution in the forming mold to obtain the ophthalmic lens; wherein the ophthalmic lens has a blue blocking rate of between 10 and 60%; and wherein the blue-filtering compound is a compound having the structural formula (a):
Figure BDA0003432985590000031
wherein R1 is hydrogen, a C1 to C10 linear or branched alkyl, a C6 to C15 aralkyl, -R2-X, -O-R2-X, or-N-R2-X; wherein R2 is a C1 to C10 linear or branched alkylene group, a hydroxyl-substituted C1 to C10 linear or branched alkylene group, or a C1 to C10 linear or branched alkylene group interrupted by an ester group, X is-OH, -OC (O) R3, -NH2, -NC (O) R3, -NCO, -COOH, or-COOR 3; wherein R3 is a C1 to C10 linear or branched alkyl group, or a C3 to C10 linear or branched alkenyl group.
In preparing the blue-filtering ophthalmic lenses of the present invention, 90.0 to 90.6 weight percent of the substrate may be employed.
According to the present invention, the substrate as described above may contain a hydrophilic substance, a polymerization initiator, a crosslinking agent, or a combination thereof.
The hydrophilic agent includes, but is not limited to, one or more of 2-hydroxyethyl methacrylate (2-Hydroxyethyl methacrylate, HEMA), methacrylic acid (2-methylpropenoic acid, MAA), acrylic Acid (AA), N-Vinyl-2-pyrrolidone (NVP), N-Dimethylacrylamide (DMAA), glycidyl methacrylate (Glycerol methacrylate, GMA), diethylaminoethyl methacrylate (2- (dimethyl amine) ethyl methacrylate, DEAEMA).
The polymerization initiator includes, but is not limited to, a thermal initiator or a photoinitiator.
The thermal initiator includes, but is not limited to, one or a combination of more than one of 2,2' -Azobisisobutyronitrile (AIBN), azobisisoheptonitrile (ADVN), benzoyl Peroxide (BPO).
The photoinitiator includes, but is not limited to, one or a combination of more than one of phenyl bis (2, 4, 6-trimethylbenzoyl) -phosphine oxide, 2-hydroxy-2-methyl-1-phenyl-1-propanone.
The crosslinking agent includes, but is not limited to, one or a combination of more than one of Ethylene Glycol Dimethacrylate (EGDMA), triethylene glycol dimethacrylate (TrEGDMA), tetraethylene glycol dimethacrylate (TEGDMA), polyethylene glycol dimethacrylate (PEGDMA), propylene-terminated ethylene oxide dimethylsiloxane-ethylene oxide ABA block copolymer, trimethylolpropane trimethacrylate (Trimethylolpropane trimethacrylate, TMPTMA).
In addition, the substrate may also include a non-hydrophilic material. The non-hydrophilic materials include, but are not limited to, (3-methacryloxy-2-hydroxypropoxy) propylbis (trimethylsiloxy) Methyl (methyldi (trimethylsiloxy) silylpropylglyceryl methacrylate, SIGMMA), methacryloxypropyltris (trimethylsiloxy) silane (3- (methylacryloxy) -propyltris (trimethylsiloxy) -silane, TRIS), polydimethylsiloxane (PDMS), or a combination of one or more of them.
According to the invention, the bluing compound as described previously may be a compound having the structural formula (a):
Figure BDA0003432985590000041
wherein R1 is hydrogen, a C1 to C10 linear or branched alkyl, a C6 to C15 aralkyl, -R2-X, -O-R2-X, or-N-R2-X; wherein R2 is a C1 to C10 linear or branched alkylene group, a hydroxyl-substituted C1 to C10 linear or branched alkylene group, or a C1 to C10 linear or branched alkylene group interrupted by an ester group, X is-OH, -OC (O) R3, -NH2, -NC (O) R3, -NCO, -COOH, or-COOR 3; wherein R3 is a C1 to C10 linear or branched alkyl group, or a C3 to C10 linear or branched alkenyl group.
The ophthalmic lens of the present invention is preferably a contact lens, such as a soft contact lens, a hard contact lens, an embedded ophthalmic lens or an artificial lens.
Drawings
Fig. 1 shows the transmittance (T%) of lenses 12-16 at each wavelength.
Detailed Description
Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs.
The term "a" as used herein, unless otherwise indicated, refers to the number of at least one (one or more).
In one aspect, the present invention provides a blue-light-filtering ophthalmic lens having a db value of less than 2, the ophthalmic lens comprising a blue-light-filtering compound and a substrate, wherein db = (b ×) is provided 1 –(b*) 0 This (b) 1 B is the value of b for the ophthalmic lens, and the (b) 0 Is the b-value of a control lens.
In another aspect, the present invention provides a blue-light-filtering ophthalmic lens having a db value of less than 2 and a blue-light blocking ratio of between 10 and 60%, the ophthalmic lens comprising a blue-light-filtering compound and a substrate, wherein db= (b) 1 –(b*) 0 This (b) 1 B is the value of b for the ophthalmic lens, and the (b) 0 Is the b-value of a control lens.
For example, the control lens is a lens without blue light filtering compound.
The b values are the values of the blue-yellow coordinate axes of the lens in the CIELAB color space. Relevant definitions regarding the CIELAB color space can be found, for example, in US 5,751,845 or US 2019/0151161.
In some embodiments of the invention, the blue-filtering compound is present in an amount of 0.4 to 10% by weight.
According to the present invention, the blue-filtering compound may be 0.4 to 10%,1 to 10%,1.5 to 10%,2 to 10%,2.5 to 10%,3 to 10%,3.5 to 10%,4 to 10%,4.5 to 10%, or 5 to 10% by weight.
According to the present invention, an ophthalmic lens as previously described may have a thickness of 0.04 to 2mm, a thickness of 0.04 to 1.95mm, a thickness of 0.04 to 1.90mm, a thickness of 0.04 to 1.85mm, a thickness of 0.04 to 1.80mm, a thickness of 0.04 to 1.75mm, a thickness of 0.04 to 1.70mm, a thickness of 0.04 to 1.65mm, a thickness of 0.04 to 1.60mm, a thickness of 0.04 to 1.55mm, or a thickness of 0.04 to 1.50 mm.
The ophthalmic lenses as described above may have a blue blocking rate of 10 to 60%, a blue blocking rate of 20 to 60%, a blue blocking rate of 30 to 60%, a blue blocking rate of 40 to 60%, or a blue blocking rate of 50 to 60%.
In yet another aspect, the present invention provides a blue light filtering ophthalmic lens, wherein the ophthalmic lens has a thickness of 0.04 to 1.5mm, a blue light blocking rate of 10 to 60%, and the ophthalmic lens comprises a substrate and a blue light filtering compound having the structural formula (a):
Figure BDA0003432985590000061
wherein R1 is hydrogen, a C1 to C10 linear or branched alkyl, a C6 to C15 aralkyl, -R2-X, -O-R2-X, or-N-R2-X; wherein R2 is a C1 to C10 linear or branched alkylene group, a hydroxyl-substituted C1 to C10 linear or branched alkylene group, or a C1 to C10 linear or branched alkylene group interrupted by an ester group, X is-OH, -OC (O) R3, -NH2, -NC (O) R3, -NCO, -COOH, or-COOR 3; wherein R3 is a C1 to C10 linear or branched alkyl group, or a C3 to C10 linear or branched alkenyl group.
In some embodiments of the invention, the blue-filtering compound is present in an amount of 0.4 to 10% by weight.
In another aspect, the present invention provides a blue-light-filtering ophthalmic lens made by a method comprising the steps ofThe preparation method comprises the following steps: mixing a blue light filtering compound and a substrate to obtain a mixed solution, wherein the weight percentage of the blue light filtering compound is 0.4 to 10.0 percent, and the weight percentage of the substrate is 90.0 to 99.6 percent; adding the mixed solution into a forming die; and causing a polymerization reaction of the mixed solution in the forming mold to obtain the ophthalmic lens, wherein the ophthalmic lens has a db value less than or equal to 2, wherein db= (b) 1 –(b*) 0 This (b) 1 B is the value of b for the ophthalmic lens, and the (b) 0 Is the b-value of a control lens.
For example, the control lens is a lens without blue light filtering compound. The b values are the values of the blue-yellow coordinate axes of the lens in the CIELAB color space.
In yet another aspect, the present invention provides a blue light filtering ophthalmic lens prepared by a method comprising the steps of: mixing a blue light filtering compound and a substrate to obtain a mixed solution, wherein the weight percentage of the blue light filtering compound is 0.4 to 10.0 percent, and the weight percentage of the substrate is 90.0 to 99.6 percent; adding the mixed solution into a forming die; and causing a polymerization reaction of the mixed solution in the forming mold to obtain the ophthalmic lens; wherein the ophthalmic lens has a blue blocking rate of between 10 and 60%; and wherein the blue-filtering compound is a compound having the structural formula (a):
Figure BDA0003432985590000071
wherein R1 is hydrogen, a C1 to C10 linear or branched alkyl, a C6 to C15 aralkyl, -R2-X, -O-R2-X, or-N-R2-X; wherein R2 is a C1 to C10 linear or branched alkylene group, a hydroxyl-substituted C1 to C10 linear or branched alkylene group, or a C1 to C10 linear or branched alkylene group interrupted by an ester group, X is-OH, -OC (O) R3, -NH2, -NC (O) R3, -NCO, -COOH, or-COOR 3; wherein R3 is a C1 to C10 linear or branched alkyl group, or a C3 to C10 linear or branched alkenyl group.
In preparing the blue-filtering ophthalmic lenses of the present invention, 90.0 to 90.6 weight percent of the substrate may be employed.
According to the present invention, the substrate may contain a hydrophilic substance, a non-hydrophilic substance, a polymerization initiator, a crosslinking agent, or a combination thereof.
The hydrophilic substances include, but are not limited to, one or more of 2-hydroxyethyl methacrylate (2-Hydroxyethyl methacrylate, HEMA), methacrylic acid (2-methylpropenoic acid, MAA), acrylic Acid (AA), N-Vinyl-2-pyrrolidone (NVP), N-Dimethylacrylamide (DMAA), glycidyl methacrylate (Glycerol methacrylate, GMA), diethylaminoethyl methacrylate (2- (dimethyl amine) ethyl methacrylate, DEAEMA), and other equivalent compounds.
The polymerization initiator includes, but is not limited to, a thermal initiator or a photoinitiator. It will be appreciated that the thermal initiator is capable of initiating a chemical reaction (polymerization) of the substrate and the blue-filtering compound upon heating, whereas the photoinitiator is capable of initiating a chemical reaction (polymerization) of the substrate and the blue-filtering compound upon illumination.
The thermal initiator includes, but is not limited to, one or a combination of more than one of 2,2' -Azobisisobutyronitrile (AIBN), azobisisoheptonitrile (ADVN), benzoyl Peroxide (BPO).
The photoinitiator includes, but is not limited to, one or a combination of more than one of phenyl bis (2, 4, 6-trimethylbenzoyl) -phosphine oxide, 2-hydroxy-2-methyl-1-phenyl-1-propanone.
Preferably, the substrate may further comprise a cross-linking agent. The crosslinking agent includes, but is not limited to, one or more of Ethylene Glycol Dimethacrylate (EGDMA), triethylene glycol dimethacrylate (TrEGDMA), tetraethylene glycol dimethacrylate (TEGDMA), polyethylene glycol dimethacrylate (PEGDMA), propylene-terminated ethylene oxide dimethylsiloxane-ethylene oxide ABA block copolymers, trimethylolpropane trimethacrylate (Trimethylolpropane trimethacrylate, TMPTMA), other equivalent compounds, or combinations thereof.
In addition, the substrate may further comprise a non-hydrophilic substance. The non-hydrophilic materials include, but are not limited to, (3-methacryloxy-2-hydroxypropoxy) propylbis (trimethylsiloxy) Methyl (methyldi (trimethylsiloxy) silylpropylglyceryl methacrylate, SIGMMA), methacryloxypropyltris (trimethylsiloxy) silane (3- (methylacryloxy) -propyltris (trimethylsiloxy) -silane, TRIS), polydimethylsiloxane (PDMS), other equivalent compounds, one or a combination of more than one.
For example, the substrate may have three forms including hydrophilic materials, including non-hydrophilic materials, or including both hydrophilic and non-hydrophilic materials.
According to the invention, the bluing compound as described previously may be a compound having the structural formula (a):
Figure BDA0003432985590000081
wherein R1 is hydrogen, a C1 to C10 linear or branched alkyl, a C6 to C15 aralkyl, -R2-X, -O-R2-X, or-N-R2-X; wherein R2 is a C1 to C10 linear or branched alkylene group, a hydroxyl-substituted C1 to C10 linear or branched alkylene group, or a C1 to C10 linear or branched alkylene group interrupted by an ester group, X is-OH, -OC (O) R3, -NH2, -NC (O) R3, -NCO, -COOH, or-COOR 3; wherein R3 is a C1 to C10 linear or branched alkyl group, or a C3 to C10 linear or branched alkenyl group.
According to the present invention, the blue-filtering compound may be a compound having the structural formula (a):
Figure BDA0003432985590000091
wherein R1 is hydrogen, a C1 to C10 linear or branched alkyl, a C6 to C15 aralkyl, -R2-X, -O-R2-X, or-N-R2-X; wherein R2 is a C1 to C10 linear or branched alkylene group, a hydroxyl-substituted C1 to C10 linear or branched alkylene group, or a C1 to C10 linear or branched alkylene group interrupted by an ester group, X is-OH, -OC (O) R3, -NH2, -NC (O) R3, -NCO, -COOH, or-COOR 3; wherein R3 is a C1 to C10 linear or branched alkyl group, or a C3 to C10 linear or branched alkenyl group.
According to some embodiments of the present invention, an ophthalmic lens having a db value of less than 2 is prepared by a process comprising the steps of: mixing a blue light filtering compound and a substrate to obtain a mixed solution, wherein the weight percentage of the blue light filtering compound is 1 to 10 percent, and the weight percentage of the substrate is 90 to 99 percent; adding the mixed solution into a forming die; and causing a polymerization reaction of the mixed solution in the forming mold to obtain the ophthalmic lens.
The prepared ophthalmic lenses may have a thickness of 0.04 to 2mm, 0.04 to 1.95mm, 0.04 to 1.90mm, 0.04 to 1.85mm, 0.04 to 1.80mm, 0.04 to 1.75mm, 0.04 to 1.70mm, 0.04 to 1.65mm, 0.04 to 1.60mm, 0.04 to 1.55mm, or 0.04 to 1.50 mm.
In addition, the prepared ophthalmic lenses may have a blue blocking rate of 10 to 60%, a blue blocking rate of 20 to 60%, a blue blocking rate of 30 to 60%, a blue blocking rate of 40 to 60%, or a blue blocking rate of 50 to 60%.
According to the present invention, the bluing compound used to prepare ophthalmic lenses may be a compound having the structural formula (a):
Figure BDA0003432985590000101
wherein R1 is hydrogen, a C1 to C10 linear or branched alkyl, a C6 to C15 aralkyl, -R2-X, -O-R2-X, or-N-R2-X; wherein R2 is a C1 to C10 linear or branched alkylene group, a hydroxyl-substituted C1 to C10 linear or branched alkylene group, or a C1 to C10 linear or branched alkylene group interrupted by an ester group, X is-OH, -OC (O) R3, -NH2, -NC (O) R3, -NCO, -COOH, or-COOR 3; wherein R3 is a C1 to C10 linear or branched alkyl group, or a C3 to C10 linear or branched alkenyl group.
The blue-filtering compound used in the present invention may have the structural formula (A1):
Figure BDA0003432985590000102
the blue-filtering compound used in the present invention may have the structural formula (A2):
Figure BDA0003432985590000103
which contains an unsaturated vinyl group.
The ophthalmic lens of the present invention is preferably a contact lens, such as a soft contact lens, a hard contact lens, an embedded ophthalmic lens or an artificial lens.
The following examples serve to further illustrate embodiments of the invention, which are illustrative and not limiting.
Example 1: preparation of ophthalmic lenses with different raw materials and raw material ratios
Lenses 1 to 11 were prepared according to the raw materials and the weight ratios thereof shown in table 1 below.
TABLE 1 raw materials weight ratio Table
Figure BDA0003432985590000111
Wherein HEMA is 2-hydroxyethyl methacrylate (2-Hydroxyethyl methacrylate), EGDMA is ethylene glycol dimethacrylate, and AIBN is 2,2' -azobisisobutyronitrile.
Taking lens 2 as an example, 0.40% by weight of a compound of formula (a), 99.20% by weight of HEMA, 0.20% by weight of EGDMA, and 0.20% by weight of AIBN were prepared, and the prepared various raw materials were filtered and mixed uniformly and placed into a molding die. Then, heating or irradiation is performed to cause copolymerization of the raw materials in the forming mold. After completion of the reaction, the lenses were peeled from the forming mold and used for subsequent analysis.
Example 2: blue light filtering capability analysis
The average blue light transmittance (%) of the lenses 1 to 11 prepared in example 1 in the wavelength range of 380 to 460nm was measured by an ultraviolet-visible light spectroluminance meter (for example, a spectroluminance meter of the model Agilent Cary 60), respectively, and the respective blue light blocking ratios (%) thereof were calculated, and were used as parameters for evaluating the power of the lens filter Lan Guangneng.
First, the lenses to be tested are equilibrated by immersing them in standard saline for at least 30 minutes. The 1cm diameter quartz cuvette was carefully removed, washed 3 times with pure water and 3 times with standard saline. And wiping the outside of the quartz tube with mirror paper, checking whether the tube wall is dirty or fingerprint, and if so, repeating the cleaning step until the quartz tube is clean or replacing the quartz colorimetric tube. The lenses were carefully placed into a cuvette and cut to the appropriate square size as needed. And starting the spectro-luminance meter and the software. The wavelength of the lens transmittance test is 380-460 nm in the blue light wavelength range. The measurement range is 380-460 nm, and the spectrum scanning bandwidth is 1nm. 8 minutes of full standard saline was added to the cuvette, and blank correction (blank) was performed on a set spectroluminance meter. Taking out the colorimetric tube, carefully placing the colorimetric tube into the lens, and confirming that the center of the lens is positioned at the light source passing position of the luminance meter. The transmittance (T%) of the lens at 380-460 nm is measured and the measurement result is stored. And the corresponding blue light filtering capacity value is calculated through the following formula 1 and formula 2:
Figure 1
light blocking Rate (%) = 100-average light transmittance (2)
The measured and calculated values for lenses 1-11 are recorded in table 2 below.
TABLE 2 blue light filtering capability values
Figure BDA0003432985590000122
As shown in table 2, lens 1 by itself still had a somewhat slight blue blocking rate (about 0.4%) without any blue filtering material added.
In the case of adding a yellow dye as a contrast compound as a blue light filtering material, a small amount (about 0.1%) was added to make the lenses exhibit a yellow appearance, which cannot meet the object of the present invention, so that the proportion of the yellow dye was reduced in lenses 7 to 11 (see table 1), and it was tested whether or not it still had the desired blue light filtering effect. The results show that a blue blocking rate of 6 to 22% can be achieved with 0.01 to 0.1% yellow dye.
Generally, the blue blocking rate of the lens is at least 10% and is considered to have the effect of filtering blue light.
In the lenses using the yellow dye, the blue blocking ratio of the lenses 7 and 8 was less than 10%, and the blue blocking ratio of the lenses 9 to 11 was more than 10%. Lenses 2 to 6 using the compound of formula (A) have a blue blocking ratio of about 10 to about 60%.
Example 3: transparency degree analysis
A color difference meter (for example, a color difference meter with a model number of MSEZ-4000S) is calibrated, and after calibration, the lens is aligned to a lens of a control group (lens 1 prepared in example 1), and the color difference meter displays the absolute value of the color of the lens of the control group by pressing a measurement key: l, a, b.
Next, the test was repeated with the measuring lens aligned with a test set of lenses (one of lenses 2-11 prepared in example 1), and the color difference meter displayed the absolute value of the test set of lenses: l, a, b.
According to the positive and negative of the color difference value, the color difference between the test group lens and the control group lens can be obtained: l represents black and white, and positive values of L represent that the lenses of the test group are whiter than the lenses of the control group, and negative values represent blacker; a represents red and green, a represents positive value, the lenses of the test group are redder than the lenses of the control group, and negative value represents greener; b represents yellow blue, b represents positive values, and negative values represent blue.
In the present invention, it was found that whether the appearance of the lens is yellowish can be determined by calculating db by the following equation 3:
(db*) test group lens =(b*) Test group lens –(b*) Lens for control group (3)
The measured and calculated values for lenses 1-11 are shown in Table 3 below, along with the apparent color and blue blocking ratio of the lenses.
TABLE 3 color difference value/appearance color/blue blocking ratio control
Figure BDA0003432985590000131
Figure BDA0003432985590000141
Lens 1 was free of any blue-filter material added, had a clear, colorless appearance for visual observation, and had a b-value of 0.00 representing yellowish green information. Lens 1 was used as a control lens.
Lenses 7 to 11 are lenses made using yellow dye. Among them, lenses 7 to 8, although showing a transparent and colorless appearance, had a blue blocking rate of less than 10% (see table 2), and did not have the required blue light filtering ability; while the blue blocking ratio of the lenses 9 to 11 was more than 10% (see table 2), the appearance thereof was observed to be yellowish by visual observation as shown in table 3.
Lenses 2 to 6 are lenses made using compounds of formula (a) which are transparent and colorless in appearance when viewed visually, and have a db value of between 0.08 and 0.87. In addition, lenses 8 with db values up to 2.01 still exhibit a clear colorless appearance, and it is inferred that lenses with db values less than 2 exhibit a non-yellowish or clear colorless appearance.
Example 4: other embodiments
Table 4 below provides relevant parameters for lenses 12-16 of other embodiments of the present invention.
TABLE 4 parameters relating to lenses 12-16
Figure BDA0003432985590000142
Fig. 1 shows the transmittance (T%) of each of the lenses 12 to 16 at each wavelength.
The foregoing description is only of the preferred embodiments of the invention and is not intended to limit the scope of the invention, i.e., all changes and modifications that come within the meaning and range of equivalency of the shape, construction, features and spirit of the invention are to be embraced by the claims.

Claims (20)

1. An ophthalmic lens for blue light filtering, characterized in that it has a db value less than or equal to 2, the ophthalmic lens comprising a blue light filtering compound and a substrate, wherein db= (b) 1 –(b*) 0 This (b) 1 B is the value of b for the ophthalmic lens, and the (b) 0 Is the b-value of a control lens.
2. An ophthalmic lens for blue light filtration, characterized in that it has a db value of less than or equal to 2 and a blue light blocking ratio of between 10 and 60%, the ophthalmic lens comprising a blue light filtering compound and a substrate, wherein db= (b) 1 –(b*) 0 This (b) 1 B is the value of b for the ophthalmic lens, and the (b) 0 Is the b-value of a control lens.
3. Ophthalmic lens according to claim 1, characterized in that it has a thickness of 0.04 to 2.00 mm.
4. The ophthalmic lens of claim 1 wherein the blue-filtering compound is present in an amount of 0.4 to 10% by weight.
5. Ophthalmic lens according to claim 2, characterized in that it has a thickness of 0.04 to 2.00 mm.
6. The ophthalmic lens of claim 2 wherein the blue-filtering compound is present in an amount of 0.4 to 10% by weight.
7. An ophthalmic lens for filtering blue light, characterized in that the thickness of the ophthalmic lens is between 0.04 and 1.5mm, the blue light blocking rate of the ophthalmic lens is between 10 and 60%, and the ophthalmic lens comprises a blue light filtering compound having the structural formula (a):
Figure FDA0003432985580000011
wherein R1 is hydrogen, a C1 to C10 linear or branched alkyl, a C6 to C15 aralkyl, -R2-X, -O-R2-X, or-N-R2-X; wherein R2 is a C1 to C10 linear or branched alkylene group, a hydroxyl-substituted C1 to C10 linear or branched alkylene group, or a C1 to C10 linear or branched alkylene group interrupted by an ester group, X is-OH, -OC (O) R3, -NH2, -NC (O) R3, -NCO, -COOH, or-COOR 3; wherein R3 is a C1 to C10 linear or branched alkyl group, or a C3 to C10 linear or branched alkenyl group.
8. The ophthalmic lens of claim 7 wherein the blue-filtering compound is present in an amount of 0.4 to 10% by weight.
9. An ophthalmic lens for filtering blue light, characterized in that it is prepared by a process comprising the steps of:
mixing a blue light filtering compound and a substrate to obtain a mixed solution, wherein the weight percentage of the blue light filtering compound is 0.4 to 10.0 percent, and the weight percentage of the substrate is 90.0 to 99.6 percent;
adding the mixed solution into a forming die; and
generating a polymerization reaction of the mixed solution in the forming mold to obtain the ophthalmic lens, wherein the ophthalmic lens has a db value less than or equal to 2, wherein db= (b) 1 –(b*) 0 This (b) 1 B is the value of b for the ophthalmic lens, and the (b) 0 Is one ofB values for control lenses.
10. An ophthalmic lens for filtering blue light, characterized in that it is prepared by a process comprising the steps of:
mixing a blue light filtering compound and a substrate to obtain a mixed solution, wherein the weight percentage of the blue light filtering compound is 0.4 to 10.0 percent, and the weight percentage of the substrate is 90.0 to 99.6 percent;
adding the mixed solution into a forming die; and
generating a copolymerization reaction of the mixed solution in the forming mold to obtain the ophthalmic lens;
wherein the ophthalmic lens has a blue blocking rate of between 10 and 60%; and
Wherein the blue-filtering compound is a blue-filtering compound having the structural formula (a):
Figure FDA0003432985580000021
wherein R1 is hydrogen, a C1 to C10 linear or branched alkyl, a C6 to C15 aralkyl, -R2-X, -O-R2-X, or-N-R2-X; wherein R2 is a C1 to C10 linear or branched alkylene group, a hydroxyl-substituted C1 to C10 linear or branched alkylene group, or a C1 to C10 linear or branched alkylene group interrupted by an ester group, X is-OH, -OC (O) R3, -NH2, -NC (O) R3, -NCO, -COOH, or-COOR 3; wherein R3 is a C1 to C10 linear or branched alkyl group, or a C3 to C10 linear or branched alkenyl group.
11. The ophthalmic lens of any one of claims 1 to 10 wherein the substrate is a soft contact lens substrate, a hard contact lens substrate, an embedded ophthalmic lens substrate or an artificial lens substrate.
12. The ophthalmic lens of any one of claims 1 to 10 wherein the substrate comprises a hydrophilic material, a polymerization initiator, a crosslinking agent, or a combination thereof.
13. Ophthalmic lens according to any one of claims 8 to 10, characterized in that the weight percentage of the substrate is 90.0 to 90.6%.
14. The ophthalmic lens of any one of claims 1 to 5 and 9 wherein the blue-filtering compound is a compound having the structural formula (a):
Figure FDA0003432985580000031
wherein R1 is hydrogen, a C1 to C10 linear or branched alkyl, a C6 to C15 aralkyl, -R2-X, -O-R2-X, or-N-R2-X; wherein R2 is a C1 to C10 linear or branched alkylene group, a hydroxyl-substituted C1 to C10 linear or branched alkylene group, or a C1 to C10 linear or branched alkylene group interrupted by an ester group, X is-OH, -OC (O) R3, -NH2, -NC (O) R3, -NCO, -COOH, or-COOR 3; wherein R3 is a C1 to C10 linear or branched alkyl group, or a C3 to C10 linear or branched alkenyl group.
15. The ophthalmic lens of claim 12, wherein the hydrophilic agent comprises one or more of 2-hydroxyethyl methacrylate (HEMA), methacrylic acid (MAA), acrylic Acid (AA), N-vinyl-2-pyrrolidone (NVP), N-Dimethylacrylamide (DMAA), glycidyl Methacrylate (GMA), diethylaminoethyl methacrylate (DEAEMA).
16. The ophthalmic lens of claim 12 wherein the polymerization initiator comprises a thermal initiator or a photoinitiator.
17. The ophthalmic lens of claim 16 wherein the thermal initiator comprises one or a combination of more than one of 2,2' -Azobisisobutyronitrile (AIBN), azobisisoheptonitrile (ADVN), benzoyl Peroxide (BPO).
18. The ophthalmic lens of claim 16 wherein the photoinitiator comprises one or a combination of more than one of phenyl bis (2, 4, 6-trimethylbenzoyl) -phosphine oxide, 2-hydroxy-2-methyl-1-phenyl-1-propanone.
19. The ophthalmic lens of claim 12, wherein the crosslinking agent comprises one or a combination of more than one of Ethylene Glycol Dimethacrylate (EGDMA), triethylene glycol dimethacrylate (TrEGDMA), tetraethylene glycol dimethacrylate (TEGDMA), polyethylene glycol dimethacrylate (PEGDMA), propylene-terminated ethylene oxide dimethylsiloxane-ethylene oxide ABA block copolymer, trimethylolpropane trimethacrylate (TMPTMA).
20. The ophthalmic lens of claim 12 wherein the substrate comprises a non-hydrophilic material comprising one or more of (3-methacryloxy-2-hydroxypropoxy) propyl bis (trimethylsiloxy) methyl (SIGMMA), methacryloxypropyl TRIS (trimethylsiloxy) silane (TRIS), polydimethylsiloxane (PDMS) or a combination thereof.
CN202111600598.4A 2021-12-24 2021-12-24 Blue light filtering ophthalmic lens Pending CN116338979A (en)

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