DD278691A3 - METHOD FOR PRODUCING UV-ABSORBENT OPTICAL MATERIALS - Google Patents

Abstract

The invention relates to a method for the production of UV-absorbing materials, in particular for use in visual aids such as intraocular lenses, trays or spectacle lenses, which can be used primarily in aphakic eyes application. The object of the invention is to improve the optical properties as well as the material properties of UV-absorbing optical materials. The object of the invention is to develop a method for producing a UV-absorbing material for visual aids, which is intended to protect the ocular fundus against damage caused by high-energy UV radiation while improving the Wellenlaengenvariation the absorption edge, especially when used on aphakic eyes. The object is achieved by means of a process for the preparation of UV-absorbing optical materials, in particular for use in vision aids by copolymerization of methyl methacrylate or 2 hydroxyethyl methacrylate with a comonomer and optionally further polymerizable compounds according to the invention by using a ungranched anthracene derivative of general formula I as comonomer becomes. Formula I

Description

Y: -X-COO; -X-CO-NH; -X-; -

X is an alkylene or arylene radical or is absent and

R is a polymerizable organic radical.

Field of application of the invention

The invention relates to a method for the production of UV-aboorbierenden optical materials, in particular for use in Sehhilfon such as intraocular lenses, trays or spectacle lenses, which can be found primarily in aphaken eyes application.

Characteristic of the known technical solutions

So far, visual aids such as trays and intraocular lenses were mainly made of polymethylmethacrylate (PMMA). A comparison of the transmission properties of PMMA and the human eye lens shows that PMMA material has an absorption edge shifted by about 100 nm to shorter wavelengths. When the human lens is replaced by a PMMA intraocular lens or when wearing an adhesive shell in aphakia, radiation with wavelengths of 300 to 400 nm thus reaches the retina unprotected. The retina of aphakic eyes is thus exposed to a higher retinal radiation intensity.

By adding conventional UV absorbers to the polymeric material, the transmission properties of PMMA can be better adapted to those of the human crystalline lens (Vieweg-Essser: Kunststoffhandbuch Vol. IX., Polymethyl methacrylate, Munich, Carl-Hanser-Verlag 1975).

The decisive disadvantages of these UV-absorbing materials is that the added low molecular weight UV absorbers ζ. B. can be washed out by ocular fluids. Chemical binding of the UV absorber to the polymer prevents its extraction. So describes z. For example, U.S. Patent 4,304,895 discloses the incorporation of substituted benzophenone derivatives (e.g., 2,2'-dihydroxy-4,4'-methacryloxybenzophenone) in PMMA to produce cornelene trapping dishes. The resulting materials have absorption edges that cut the short-wave radiation range to a maximum of 390 nm even at high benzophenone derivative concentrations. The benzophenone derivatives used are also not resistant to hydrolysis and have free phenolic OH groups which could be physiologically active. Moreover, it may in the use of vinyl derivatives of known UV absorbers to other problems, such. B. slow polymerization or formation of low molecular weight products that arise from the chain transferring or terminating effect of such compounds, as it is z. 1, Wiley-Intersci., Publ., 1967, p. 57, I. Brandrup, EH Immergut, Polymer Handbook, Wiley-Intersci. Publ. 1975, p. II-53).

Object of the invention

The aim of the invention is to improve the optical and the material properties of UV-absorbing optical materials, in particular of visual aids.

Explanation of the essence of the invention

The object of the invention is a method for producing a UV-absorbing material for Sehhilfei; to develop, especially in the application of aphakic eyes to protect the ocular fundus from damage by enerc, ie ^r eche UV radiation while improving the wavelength variation of the absorption edge.

The object is achieved by means of a process for the preparation of UV-absorbing optical materials, in particular for vision aids, by copolymerization of methacrylate or 2-hydroxyethyl methacrylate with a comonomer in concentrations of 0.3-0.7% by weight in%, optionally with further polymerizable compounds according to the invention in that is used as Comonomei an unsaturated anthracene derivative of the general formula I.

(Formol I)

and Y: -X-COO-; -X-CO-NH; -X-; -, wherein X represents an alkylene or arylene radical or is omitted and R is a polymerizable organic radical.

The substitution of anthracene is preferably in the 1-, 2- or 9-position.

The mass fraction of the anthracene derivative is in a range of 0.001 to 10% by mass.

By suitable choice of the substitution of the anthracene and the copolymeric composition, the absorption edge of the material is varied in the range between 320 and 450. Thus, it has been found that the polymer-bound anthracene derivatives form UV-opaque, transparent grains, the UV absorber due to its polymer bond z. B. is not leachable by an aqueous medium such as physiological saline.

If Y represents a COO group, then RCOO- represents a polymerizable acyl radical, eg. As the acrylic acid, methacrylic acid or other unsaturated acid. If Y is absent, then R represents a polymerizable alkyl radical of, for example, In addition, other comonomers can control the physical properties of the material by influencing the hydrophilicity / hydrophobicity or by crosslinking. Accordingly, the incorporation of 2-hydroxyethyl methacrylate causes an increase in the hydrophilicity, styrene derivatives, however, a hydrophobing and the use of Dimethacrylatvernetzern an increase in stability.

The novel process can preferably be carried out as radical copolymerization in bulk, it being possible to use conventional initiators, such as dibunozoyl peroxide or azobisisobutyronitrile.

The UV-absorbing material produced by the method according to the invention has a high chemical stability compared to known UV-absorbing materials which are used as optically active media in vision aids. The wavelength variation of the absorption edge can be carried out in a wide range, which significantly expands the possible uses of this material.

embodiments

The. The invention will be explained in more detail by means of the following examples:

Example 1:

Be 98g methyl methacrylate for the production of UV-absorbing materials, 0.5mA .-% 9-vinyl anthracene and 0.05 mA .-% dibenzoyl peroxide in sealed ampoules first 10h at 6O ⁰ C, then 10h at 70 ° C, 10h at 8O ⁰ C and finally heated to 120 C for 40 h. After cooling, a clear, transparent cylinder body is obtained which can be sliced down by mechanical processing. The polished discs show the transmission properties given in Table 1, with no detectable organic constituents being released from the samples thus prepared in physiological saline solution at a temperature of 40 ^° C.

Example 2:

It is prepared according to Example 1, a material, being used as the polymerizable UV absorber 0.5Ma .-% 1-vinyl anthracene application. The transmission properties are shown in Table 1.

Example 3:

It is prepared according to Example 1, a material in which 0.5Ma .-% 2-vinylanthracene is used as the polymerizable UV absorber. The transmission properties are shown in Table 1.

Table 1; Transmission of polymer samples of a layer thickness of 1 mm at different concentrations of the UV absorber

concentration 1-VA " ¹ 0.3 0 9-VA 1-VA 0.5 9-VA 1-VA 0.7 0 9-VA UV absorbers 2-VA 0 transm 2-VA 2-VA 0 (Nm) Transmission (%) 0 0 0 ission (%) 0 Transmission (%) 0 0 350 0 0 0 0 0 0 0 0 0 360 0 0 0 0 0 0 0 0 0 370 0 1 0.3 0 0 0 0 0 0 380 0 10 2.5 0 0 0.2 0 0.2 0 390 0 65 29 0 0 12 0 31 3.4 400 0.2 86 69 1.1 0 54 0 68 36 410 7 91 81 39 2.1 71 0 80 57 420 57 92 87 71 49 81 21 82 51 430 81 91 79 78 86 57 80 440 86 92 84 86 89 69 82 450 89 89 76

VA = vinyl anthracene

Claims (2)

Process for the preparation of UV-absorbing optical materials, in particular for vision aids, by copolymerization of methyl methacrylate or 2-hydroxyethyl methacrylate with a comonomer in concentrations of 0.3-0.7 parts by weight in%, optionally with further polymerizable compounds, characterized in that the comonomer used is an unsaturated anthracene derivative of the general formula I, i ^: iu * nu: l I. · '""^' ^