Compositions and methods for manufacturing ophthalmological lenses

FIELD: polymer materials.

SUBSTANCE: invention provides composition containing from about 50 to about 80% of component selected from group consisting of di(meth)acylate of ethoxylated bisphenol A, di(meth)acylate of non-ethoxylated bisphenol A, di(meth)acylate of propoxylated bisphenol A, epoxy(meth)acrylates of bisphenol A, and mixtures thereof; from more than 0 to about 30% of component selected from group consisting of tetrahydeofuryl (meth)acrylate, isobornyl (meth)acrylate, cyclohexyl (meth)acrylate, and mixtures thereof; from more than 0 to about 15% of component selected from group consisting of dipentaerythritol penta(meth)acrylate, trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, tri(meth)acrylate of ethoxylated or propoxylated trimethylolpropane, tri(meth)acrylate of ethoxylated or propoxylated glycerol, pentaerythritol tetra(meth)acrylate, bis-trimethylolpropane tetra(meth)acrylate, dipentaerythritol hexa(meth)acrylate, and combinations thereof. Such composition is suited to manufacture eyeglass lenses.

EFFECT: expanded possibilities in manufacture of polymer-based lenses, including multifocal ones.

21 cl, 3 tbl, 18 ex

 

This invention relates to ophthalmic lenses. In particular, the invention provides compositions for the production of lenses by casting.

The prior art inventions

The use of spectacle lenses for the correction of ametropia is well known. For example, a multi-focus lenses, such as progressive summarizing lens, is used to treat senile hyperopia. There are several known methods of manufacturing ophthalmic lenses. Such methods include casting preliminary preparations for the lenses and the subsequent polishing and grinding of workpieces with the formation of lenses, casting the whole of the lens and the coating of the surface layer by molding the optical capsule or preformed blank with the formation of the lens.

Applying a layer by molding the optical preformed workpiece is preferable because it can reduce the number of molds required for obtaining all the necessary spacing of the lenses. However, the known polymers for use in the casting of the whole lens can be suitable for surface application by moulding on preformed billet. For example, the polymer used in the coating of the surface layer by casting on a preformed billet must adhere to the workpiece. In addition, the unknown is panorama the result is compression of the applied layer of the casting. Therefore, the invention provides compositions suitable for applying a layer by molding preformed blanks with the formation of the lenses.

Description of the invention and its preferred executions

This invention provides compositions for the production of ophthalmic lenses, including multi-focal spectacle lenses, such as progressive summarizing lenses and methods of making compositions according to the invention. The compositions are suitable for use in the manufacture of ophthalmic lenses by casting surface layer on a preformed blank (preform). Under "optical preformed billet" or "preform" understand optically transparent product that can refract light and suitable for use in the manufacture of eyeglass lenses. Preferably the lens is obtained by the use of compositions according to the invention is a spectacle lens, more preferably multicentric, most preferably progressive summarizing lens.

In one embodiment, the invention provides a composition consisting mainly of from about 50 to 80 weight percent of diacrylate ethoxylated bisphenol a, diacrylate methoxyethanol bisphenol a, diacrylate propoxyethanol bisphenol a, epoxy is Krylatov bisphenol or mixtures thereof, from about 5 to about 40 weight percent of benzoylacrylate, from about 0 to about 30 weight percent of tetrahydrofurfurylamine, isobutylacetate, cyclohexylacetate or mixtures thereof, and from about 0 to about 15 weight percent of pentaacetate of dipentaerythritol, triacrylate of trimethylolpropane, triacrylate pentaerythritol, triacrylate ethoxylated or propoxyethanol of trimethylolpropane, triarilmetanovogo or propoxyethanol glycerin, tetraacrylate pentaerythritol, tetraacrylate of detromethorphan, exactimate of dipentaerythritol or combinations thereof. Instead of the above acrylates can be used corresponding methacrylates or derivatives of styrene, but preferably use the acrylates.

The opening of this invention is that the composition of the invention is able to provide the layer casting having a sufficiently high modulus of deformation resistance at voltages that may occur during processing, such as lateral compression, cutting grooves in the periphery of the lens. In addition, the layer casting has a glass transition temperature ("TD") above the room temperature, so that the layer supports the dimensional stability even under extreme ambient conditions. Optionally, the layer of casting shows adhesion to the surface on which of the cast, sufficient to resist delaminating, if the lens is subjected to lateral compression and inserted into a frame. Finally, a layer of the casting also has a refractive index from about 1.55V to about 1,56 in dry condition.

Preferably use component ethoxylated bisphenol of the formula:

where each of x and y independently of one another have the value 1, 2 or 3 and x+y=2 or 3. Suitable components ethoxylated bisphenol a commercially available. In the composition of the invention, the mass percent of ethoxylated bisphenol a can be from about 50 to about 80, preferably from about 55 to about 65 weight percent by weight of the total polymeric composition. Preferably the degree of amoxilonline diacrylate bisphenol a is equal to or less than about 6. Can be used a mixture of ethoxylated bisphenol a, providing that about 80 mass% or more has at least 4 to 5 ethoxylated structural elements.

The discovery of this invention is that when using relatively short-chained components bisphenol get cured polymer with a high refractive index. Additionally, the use of about 50 or more weight percent short-chained component bis is the enol And the layer casting provides that, that the AP layer at least on 15°C above room temperature, and that he (layer) has a modulus above about 1500 MPa.

Benzoylacrylate preferably used in the compositions of the invention in a mass percent of about 5 to about 40, preferably about 10 to about 30 weight percent by weight of the total polymeric composition. The discovery of the invention is that benzoylacrylate preferably selected in comparison with phenoxyethylacrylate as high amoxilonline in such a composition layer of the casting becomes sensitive to oxidation and eventually turns yellow.

Preferably tetrahydrofurfurylamine used in amounts from about 0 to about 30, preferably from about 2 to about 30 and more preferably from about 5 to about 15 weight percent. Pentakill of dipentaerythritol also preferably used in the compositions of the invention in a mass percent of about 0 to about 15, preferably from about 0.5 to about 8, more preferably from about 2 to about 8 weight percent. Each of these components are commercially available.

Specialist in the art understands that the curing composition of the invention may be made by any suitable method of curing, including, but not limited to, curing ultrafioletowymi light, thermal, microwave and infrared radiation, and only one of them or in combination. Preferably UV-curing applied using UV light both high and low intensity. Thus, in a preferred embodiment of the invention provides a method for the production of lenses comprising, consisting essentially of and consisting of the following stages: a) UV-light of low intensity at injection-molding machine (Assembly) and a composition comprising, consisting mainly consisting of from about 50 to 80 weight percent of diacrylate ethoxylated bisphenol a, from about 5 to 40 weight percent of benzoylacrylate, from about 0 to about 30 tetrahydrofurfurylamine and from about 0 to about 15 pentaacetate of dipentaerythritol, under conditions suitable to convert at least about 50 percent or more reactive groups of the composition; and b) the subsequent impact on the composition of the UV light of high intensity under conditions suitable to complete the curing of the composition.

In the first stage of the method of the invention injection-molding machine is exposed to ultraviolet light of low intensity. For the purposes of the invention UV-light of low intensity is UV light with an intensity of about 0.5 to about 50, preferably primer is from 1 to about 5 mW/cm 2. Suitable wavelengths for carrying out this stage of the process are from about 300 to about 450, preferably from about 360 to about 400 nm. Impacts of low intensity is carried out in terms of wavelength and time suitable to convert at least 50 percent or more reactive groups of the molding composition and, preferably, while maintaining the polymerization rate so low as possible; and the velocity is the speed at which avoid defects caused undesirable puckering. Specialist in the art understands that the specified speed is dependent on several factors, including, without limitation, the used composition and layer thickness of the casting. Maintaining a low polymerization rate reached by the application of UV light of low intensity and, possibly, one or more photoinitiator at a concentration of about 1 mass% or less based on the total weight of the composition, including periods of newscastle cycle impacts of low intensity, and combinations thereof.

The exposure time of low intensity depends on the composition of the casting on preformed workpiece, the type and quantity of initiator used, the viscosity of the molding composition, the nature of the reactive groups, the thickness of the s layer, who should be cast, and the intensity of the UV light. Usually the total exposure time is up to about 130 seconds, preferably from 5 seconds to about 130 seconds, more preferably from about 60 seconds to about 120 seconds.

Impacts of low intensity preferably carry out (spend) in one stage. However, some set of lenses may require exposure to low intensity in two or more stages with application periods newscastle UV light from about 5 to about 60 seconds between each exposure to low intensity. Preferably the exposure time periods of from about 30 to about 60 seconds interspersed with periods of newscastle from about 5 to about 60 seconds.

After exposure to low-intensity injection-molding machine (Assembly) exposed to UV light of high intensity under conditions suitable to complete the curing of the molding composition. The intensity of UV light for the specified stage can range from about 50 to about 2000, preferably from about 500 to about 1500 mW/cm2. The wavelength at which can be produced effects may be and preferably is the same as that used when conducting the impact of low intensity. The same factors that determine the time in which the effects of low intensity are crucial for the effects of high intensity. Typically, the exposure time is from about 3 seconds to about 60 seconds, preferably from about 5 seconds to about 15 seconds. The influence of high intensity can be and preferably is carried out as a single continuous exposure. However, exposure to high intensity can also be carried out using alternating periods of exposure to UV and periods newscastle.

Stage low - and high-intensity polymerization can be carried out at ordinary temperature and atmospheric pressure. Preferably the composition is applied hot and the polymerization process is carried out at a temperature of about the glass transition temperature TD utverzhdenii song, or above it. Under "cause hot" understand that the composition is heated prior to casting to its approximate Dt. Heating can be accomplished in any suitable way, including, without limitation, furnace, heat circulating pump or a combination of both. Polymerization at a preferred temperature also perform any suitable way, including, but not limited to, maintaining the camera curing at a preferred temperature by means of forced air.

UV low and high intensity can be checked in any form, which ensure which ensures uniform distribution of light injection device. A convenient and preferred method is the impact on the injection device of UV light at the location of the source of UV light below the injection device. Sources of UV light of low intensity include, without limitation, mercury and xenon arc lamps, incandescent lamps fluorescent type or the like, and combinations thereof. Sources of UV light of high intensity are, without limitation, mercury, xenon, mercury-xenon arc lamp that emits microwave lamp FUSION™ or the like, and combinations thereof. Suitable sources of UV light used in the invention, commercially available.

Molding installation or Assembly composed of one or more "parts" (parts) plastic injection moulds, optical preformed blanks (preforms) and molding compositions. Used half / half molds made from any suitable material, including, but not limited to, glass or plastic. Used preformed blanks in the injection molding installation can be made from any suitable material, including, but not limited to, polycarbonates, such as polycarbonates of bisphenol a, carbonates alidigitaly, such as ballingarrane diethylene glycol (CR-39TM), complex allyl esters, such as treelistener, triallists is at and triethylcitrate, acrylic esters, acrylates, methacrylates, such as methyl-, ethyl - and butylmethacrylate and acrylates, derivatives of styrene, polyesters, phosphines oxides of polyethers and the like, and combinations thereof. Preformed workpiece can be obtained by any convenient means, including, without limitation, injection molding, injection press molding, the molding sheet thermoplastic, molding or the like.

Applicable in the invention initiators are those which are able to initiate the polymerization molding of the polymer by the selected method of polymerization with participation without restriction of harmonization, photoinitiators and combinations thereof. Preferably the selected photoinitiator. Suitable initiators are not limited to photoinitiator, generating free radicals, fotonation initiators, photosmovie initiators and mixtures thereof. Suitable initiators that generate free radicals, are, without limitation, methylbenzofuran, aromatic ketones, including, without limitation, 2-hydroxy-2-methyl-1-phenylpropane-1-it, 1-hydroxycyclohexane, 2,2-di-sec-butoxyethanol, 2,2-diethoxyacetophenone, 2,2-diethoxy-2-phenylacetophenone, 2,2-dimethoxy-2-phenylacetophenone, simple benzoylmethylene ether, simple benzonitrile ether, benzoin, benzil, benzyldimethyl the , benzyldimethyl, 2,2-dihydroxybenzophenone, benzylideneacetophenone, benzophenone and acetophenone, oxide, 2,4,6-trimethylbenzenesulfonyl and the like, and combinations thereof. Suitable initiators that generate free radicals, which are commercially available or known methods for their preparation.

The amount of initiator used depends on the type of initiator, as well as on the composition of the used composition. Generally, the amount of initiator will be an amount effective to initiate polymerization, from about 0.1 to about 5 weight percent by weight of the polymer composition, preferably from about 0.1 to about 1 weight percent. In addition to a suitable initiator composition of the invention may contain any desired additives, including, but not limited to, suturing, regulating the viscosity agents, and the like, and combinations thereof.

The viscosity of the molding composition can be from about 5 to about 500, preferably less than about 300, more preferably from about 5 to about 300, most preferably from about 5 to about 100 centipoise, measured at 25°With a Brookfield viscometer. Specialists in the art will understand that the mass percent of mono - and polyfunctional monomers must be controlled in such a way as to achieve the desired viscosity.

Consequently, the sustained fashion, the glass transition temperature or AP used utverzhdenii composition preferably greater than 45°C. the Specialists in the art will understand that the AP utverzhdenii composition should not be significantly different, preferably not more than about 1 to about 10°With, from that of the material used for molding the optical preformed blanks. Preferably TD utverzhdenii composition and optical material preformed workpiece is essentially the same. Additionally, the specialist in the art will understand that the desired TD utverzhdenii compositions can be achieved through the selection of monomers and their concentrations.

The mixture of the selected monomers may be from about 0.4 to about 0.6 equivalent of reactive groups per 100 g of composition. Preferably used a mixture of monomers contains from about 0.4 to about 0.6 equivalent of reactive groups per 100 g of composition. The amount of injection of the composition should be an amount effective to form a surface, and this number depends on the selected song, the parameters of the desired surface, which must be formed, and the size and shape of the surface on which the composition to be molded. Generally, the amount used of the composition extending t is from about 2 to about 20,

Casting the composition on a preformed blank with the formation of the surface layer or layers may be performed by any known method. Suitable methods of applying one or more surface layers by moulding on preformed billet proposed in patents. USA Nos. 5147585, 5178800, 5219497, 5316702, 5358672, 5480600, 5512371, 5531940, 5702819, 5793465, 5859685, 5861934 and 5907386 listed here as references.

Typically molding composition is distributed in the molding device, using any suitable methods, such as the use of a piston pump. Preferably the injection unit consists of half molds and optical preformed workpiece, where the workpiece acts as the second half of the form. The composition may be distributed in such a way as to form, after curing convex or concave surface, or both, preferably a convex surface on the preformed workpiece. Preferably half of the form set, the polymer is spread on the surface of the halves of the form and preformed workpiece is then brought into contact with the polymer by placing the preformed billet on the composition. After half form and preformed billet are chelation is determined as being way in the injection device may be allocated additional composition to ensure the removal of air bubbles and voids.

Preferably used half or halves of the molds are larger in diameter than the optical preformed billet. This allows the sealing composition without the use of gaskets, sealing rings or similar devices. In these cases, in which the radius of curvature of the surface of the preformed workpiece in contact with the composition and half forms less than half of the forms, it may be necessary to use intermediate means. Under "intermediate means" understand any device that is suitable for use in maintaining the desired distance between the surface of the halves of the form and surface of the optical preformed workpiece in contact with the composition. An exemplary device for use as an intermediate means, without limitation, are tapes, gaskets, O-rings and the like.

Possible, and preferably, in the subsequent disassembly of the injection device, the lens is heated for a time and at a temperature sufficient to relieve stresses generated in the polymerization process. Heating may be carried out in any convenient way is om, including, without limitation, the use of thermal, infrared or microwave energy, or combinations thereof. Preferably the lens is heated using thermal energy, within about 1 to about 30, preferably from about 5 to about 15 minutes at a temperature of from about 50 to about 125, preferably from about 80 to about 110°C.

The invention will be clarified with the following, not limiting examples.

Examples 1-18 (see table 1-3)

Was used the following procedure for forming lenses using the compositions and methods of the invention. Was used molding composition of the following composition: SR™285 - tetrahydrofurfurylamine; SR™349 - diacrylate ethoxylated bisphenol a (3 mol); SR™399 pentakill of dipentaerythritol and IRGACURE™ 184 - 1-hydroxycyclohexane. Mass percentages shown in the tables. Approximately 3.0 g of each composition were distributed on the concave side of the glass forms, which had 81 mm in diameter. 70-mm polycarbonate optical preformed billet was placed on the composition and with a pipette and distributed additional composition to ensure the absence of air bubbles or voids between the glass form and preformed billets.

The source of UV-light was placed below the stack is annoy form. The composition was then subjected to UV-light intensity of approximately 2.5 mW/cm2and a wavelength of about 300-380 nm for 2 minutes, followed by intensity of approximately 700 mW/cm2and a wavelength of 300-380 nm for 18 sec. The lens formed from the composition and preformed blanks, were picked out manually and annealed for 10 min at 100°in a convection oven.

1. Composition containing

from about 50 to about 80 wt.% component selected from the group consisting of di(meth)acrylate ethoxylated bisphenol a, di(meth)acrylate methoxyethanol bisphenol a, di(meth)acrylate propoxyethanol bisphenol a, epoxy(meth)acrylates of bisphenol a and mixtures thereof;

from about 5 to about 40 wt.% benzyl(meth)acrylate;

from more than 0 to about 30 wt.% component selected from the group consisting of tetrahydrofurfuryl(meth)acrylate, isobornyl(meth)acrylate, cyclohexyl(meth)acrylate or mixtures thereof; and

from more than 0 to about 15 wt.% component selected from the group consisting of Penta(meth)acrylate of dipentaerythritol, three(meth)acrylate of trimethylolpropane, three(meth)acrylate of pentaerythritol, three(meth)acrylate ethoxylated or propositionalization, three(meth)acrylate ethoxylated or propoxyethanol glycerol, Tetra(meth)acrylate of pentaerythritol, Tetra(meth)acrylate of detromethorphan, hexa(meth)acrylate of dipentaerythritol and their combinations.

2. The composition according to claim 1, characterized in that used bisphenol of the formula

where each of x and y independently of one another have the value 1, 2 or 3 and x+y=2 or 3.

3. The composition according to claim 2, characterized in that diacrylate ethoxylated bisphenol a is present in an amount of from about 55 to about 65 wt.%.

4. The composition according to claim 3, characterized in that the degree of amoxilonline diacrylate bisphenol a is equal to or less than about 6.

5. Composition according to any one of claim 2, 3 or 4, characterized in that benzoylacrylate taken in an amount from about 10 to about 30 wt.%, tetrahydrofurfurylamine used in an amount of from about 5 to about 15 wt.% and pentakill of dipentaerythritol used in an amount of from about 2 to about 8 wt.%.

6. The spectacle lens containing preformed blank and the layer containing from about 50 to about 80 wt.% component selected from the group consisting of di(meth)acrylate ethoxylated bisphenol a, di(meth)acrylate methoxyethanol bisphenol a, di(meth)acrylate propoxyethanol bisphenol a, epoxy(meth)and is relativ bisphenol or mixtures thereof; from about 5 to about 40 wt.% benzyl(meth)acrylate; from more than 0 to about 30 wt.% component selected from the group consisting of tetrahydrofurfuryl(meth)acrylate, isobornyl(meth)acrylate, cyclohexyl(meth)acrylate or mixtures thereof; and from greater than 0 to about 15 wt.% component selected from the group consisting of Penta(meth)acrylate of dipentaerythritol, three(meth)acrylate of trimethylolpropane, three(meth)acrylate of pentaerythritol, three(meth)acrylate ethoxylated or propoxyethanol of trimethylolpropane, three(meth)acrylate ethoxylated or propoxyethanol glycerol, Tetra(meth)acrylate of pentaerythritol, Tetra(meth)acrylate of detromethorphan, hexa(meth)acrylate of dipentaerythritol and their combinations.

7. The spectacle lens according to claim 6, characterized in that the component bisphenol a layer has the formula

where each of x and y independently of one another have the value 1, 2 or 3 and x+y=2 or 3.

8. The spectacle lens according to claim 6, characterized in that diacrylate ethoxylated bisphenol a layer is present in an amount of from about 55 to about 65 wt.%.

9. The spectacle lens of claim 8, characterized in that the degree of amoxilonline diacrylate bisphenol a is equal to or less than about 6.

10. The spectacle lens according to any one of claims 7, 8 or 9, characterized in that benzoylacrylate taken in an amount from about 10 to example is about 30 wt.%, tetrahydrofurfurylamine used in an amount of from about 5 to about 15 wt.% and pentakill of dipentaerythritol used in an amount of from about 2 to about 8 wt.%.

11. The method of manufacturing ophthalmic lenses containing stages: a) exposure to ultraviolet light of low intensity from about 0.5 to about 50 mW/cm2at a wavelength of from about 300 to about 450 nm on an injection molding device, and forming a layer of an effective amount of the composition under item 1, and the UV-light low intensity perform under conditions suitable to convert at least 50 percent or more reactive groups of the composition; and b) the subsequent impact on the composition of the UV light of high intensity from about 50 to about 2000 mW/cm2at a wavelength of from about 300 to about 450 nm under conditions suitable for essentially complete curing of the composition and formation of the lens.

12. The method according to claim 11, characterized in that stage a) and (b) perform at about Tg utverzhdenii composition.

13. The method according to claim 11, characterized in that it additionally contains up to stage (a) heating the composition to about Tg utverzhdenii composition.

14. The method according to item 12, characterized in that the impact of low intensity perform within from about 5 to about 300, and exposure to high intensity of halogen with exceptiona is performed for from about 3 to about 60 C.

15. The method according to 14, characterized in that the total time of exposure to ultraviolet light is about 130 or less.

16. The method according to claim 11, characterized in that the composition contains from about 50 to about 80 wt.% diacrylate ethoxylated bisphenol a, from about 5 to about 40 wt.% benzoylacrylate, from over 0 to about 30 wt.% tetrahydrofurfurylamine and from more than 0 to about 15 wt.% pentaacetate of dipentaerythritol.

17. The method according to 17, characterized in that the component bisphenol has the formula

where each of x and y independently of one another have the value 1, 2 or 3 and x+y=2 or 3.

18. The method according to p, characterized in that diacrylate ethoxylated bisphenol taken in an amount from about 55 to about 65 wt.%.

19. The method according to p, characterized in that the degree of amoxilonline diacrylate bisphenol a is equal to or less than about 6.

20. The method according to any of p, 19 or 20, characterized in that benzoylacrylate taken in an amount from about 10 to about 30 wt.%, tetrahydrofurfurylamine used in an amount of from about 5 to about 15 wt.% and pentakill of dipentaerythritol used in an amount of from about 2 to about 8 wt.%.

21. The method according to claim 11 or 17, characterized in that after stage b) further comprises the stage of heating the lens with POM is using thermal energy within from about 1 to about 30 minutes at a temperature of from about 50 to about 125° C.



 

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