Tri-functional uv-absorbing compounds and use thereof
A compound and ultraviolet absorber technology, applied in the field of compounds for preparing ophthalmic lenses, can solve the problems of uneven photopolymerization, invalid composition, etc.
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[0127] Essentially all materials known in the art for making molds can be used to make molds for ophthalmic lenses. For example, polymeric materials such as polyethylene, polypropylene, polystyrene, PMMA, cyclic olefin copolymers (e.g. COC from Ticona GmbH of Frankfurt, Germany and Summit, New Jersey; and From Zeon Chemicals LP, Louisville, KY) et al. Other materials that allow transmission of UV light such as quartz glass and sapphire can be used.
[0128] Once the lens-forming material is poured into the mold, the lens-forming material cures (ie, polymerizes) and produces the polymer matrix and final lens. The technique for carrying out the polymerization step will vary depending on the choice of lens forming material. In one aspect, when the lens-forming material includes a prepolymer comprising one or more actinically crosslinkable ethylenically unsaturated groups, the mold containing the mixture can be exposed to actinic radiation in a steric confinement to Polyme...
Embodiment 1
[0137] This example illustrates the preparation of a trifunctional UV absorber according to the invention, UVA1, based on the following scheme.
[0138] step 1:
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[0140] Step-2:
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[0142] A mixture of 500 mg (2.22 mmol) 1, 245 mg (2.45 mmol) succinic anhydride, 247 mg (2.47 mmol) TEA and 10 ml toluene was refluxed for 5 hours under nitrogen atmosphere. The reaction mixture was cooled to ambient temperature, the solvent was evaporated under reduced pressure, the residue was dissolved in 10 ml ethyl acetate and washed with 5 ml 1N HCl. Dilute the organic layer in Na 2 SO 4 Dry on top. The solvent was removed under reduced pressure and the resulting Intermediate 2 was dried under vacuum at 30 °C. 1H-NMR (400MHz, DMSO-D 6 )δ results are: 1.35 (s, 6H), 2.47-2.54 (m, 4H), 4.27-4.26 (d, J=4Hz, 2H), 4.370-4.358 (d, J=4.8Hz, 2H), 5.68 (bs, 1H, OH), 7.03-7.01 (d, J=8.8Hz, 2H), 8.22-8.19 (d, J=8.8Hz, 2H), 12.24 (bs, 1H, COOH). Mass was determined to be 325 ...
Embodiment 2
[0145] This example illustrates the synthesis of a trifunctional UV absorber of the invention, UVA2, according to the following scheme.
[0146] step 1
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[0148] step 2
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[0150] NaH 60% (0.246 g, 6 mmol) was added to a stirred solution of compound-1 (1 g, 3 mmol) and 2 ml HMPA in 20 ml dry THF at 0° C. under nitrogen atmosphere. After 10 min, a solution of dimethylmalonyl chloride (3 mmol, freshly prepared from dimethylmalonic acid and oxalyl chloride) in dry THF was added dropwise to the reaction mixture at 0°C. The reaction mixture was stirred at 0 °C for 1 h, then the reaction mixture was quenched with 1N HCl (20 ml), extracted with DCM, and dissolved in Na 2 SO 4 Dry over and concentrate under reduced pressure to give crude intermediate (2).
[0151] The crude intermediate (2) above was dissolved in THF (20ml), treated with 0.2M (10ml) LiOH in water and stirred overnight at ambient temperature. THF was evaporated under reduced pressure and the r...
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