Photochromic compositions and articles comprising polyether oligomers
A photochromic, composition technology, applied in optics, optical components, optical components, etc., which can solve the problems of different fading rates, unnoticeable color changes of mixtures, and reduced fading rates.
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Embodiment 1
[0448] step 1
[0449] Polyethylene glycol methacrylate succinate (526g / mol)
[0450]
[0451] Poly(ethylene glycol) (560) methacrylate (7.56g, 13.5mmol), succinic anhydride (1.35g, 13.5mmol), triethylamine (1.38g, 13.6mmol) and 4-dimethylaminopyridine (0.014g, 1.15×10 -4 mol) solution in dichloromethane (50ml) in N 2 Heating under slow reflux for 1 hour. The solvent was removed in vacuo to afford the title compound as a colorless viscous oil (8.94 g, 99%) pure enough for further reaction.
[0452] 1 H NMR ((CD 3 ) 2 CO) δ = 1.92 (3H, s), 2.51 (2H, d J 5.49), 2.55 (2H, d J 5.49), 3.58 (34H, bs), 3.66 (2H, t J 4.94), 3.72 (2H, t J 4.94), 4.17 (2H, t J 4.76), 4.25 (2H, t J 4.76), 5.64 (1H, s), 6.08 (1H, s).
[0453] step 2
[0454]9'-(Polyethylene glycol)(526)methacrylate-succinyloxy))-1,3,3-trimethylspiro[indoline-2,3'-[3H]naphtho [2,1-b][1,4]oxazine]
[0455]
[0456] 4-Dimethylaminopyridine (0.025g, 2.05×10 -4 mol) was added to polyethylene glycol methacryla...
Embodiment 2
[0463] Step 1. Succinyl Chloride Polyethylene Glycol (526) Methacrylate
[0464]
[0465] Magnetic stirring the polyethylene glycol methacrylate (526g / mol) succinic acid (4.66g, 8.09mmol), thionyl chloride (2.64g, 1.6mL, 22.3mmol) and three drops A solution of DMF in dichloromethane (50 mL) was refluxed under nitrogen for 2 hours. The solvent was removed in vacuo, thus obtaining the desired product (4.5 g, 95%) as a pink gel, sufficiently pure for further use.
[0466] 1H NMR ((CH3)2O)δ1.92(3H, s), 2.75(2H, t J 6.0), 3.34(2H, t J 6.0), 3.40(2H, m), 3.59(30H, bs), 3.67 (2H, m), 3.73 (2H, m), 4.23 (4H, m), 5.64 (1H, s), 6.08 (1H, s).
[0467] Step 2. 5-Methylcarboxylate-6-(poly(ethylene glycol)(526)methacrylate succinyloxy)-2,2-bis(4-methoxyphenyl)-2H- Naphtho[1,2-b]pyran
[0468]
[0469] A solution of polyethylene glycol methacrylate (526) succinyl chloride (prepared in step 1) (0.36 g, 0.766 mmol) in dichloromethane (5 mL) was slowly added to 5-methylcarboxylate- 6...
Embodiment 3
[0477] Dyes were tested by dissolving them in standard monomer mixtures followed by simple heat curing. The selected monomer mixture is polyethylene glycol 400 dimethacrylate (known as 9G) and 2,2'-bis[4-methacryloyloxyethoxy]phenyl] in a weight ratio of 1:4 A mixture of propane (known as Nouryset 110) (shown below), and 0.4% AIBN initiator. This formulation will be referred to as Monomer Mix A. Dye is added to the formulation such that the dye concentration ranges from 0.3 mg / g to 5 mg / g. The mixture was polymerized at 75°C for 16 hours in a small gasket between microscope slides to obtain test lenses of approximately 14 mm in diameter and 2 mm in thickness. The Tg of the test lens made from 9G and Nouryset 110 only was 120°C.
[0478]
[0479] All measurements can be performed on custom optical benches. The optical bench consists of a Cary 50 Bio UV-visible spectrophotometer equipped with a Cary Peltier accessory for temperature control, a 280W Thermol--Oriel xenon ar...
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