Curable photochromic compositions and optical articles prepared therefrom
The present invention provides a curable, organic polymeric photochromic composition comprising: a photochromic amount of at least one photochromic material; a polymeric polyol having carbonate groups along its backbone and having a number average molecular weight greater than 5000 g/mole; and a curing agent having reactive functional groups capable of reacting with hydroxyl groups on the polymeric polyol. After curing and after the Photochromic Performance Test the composition demonstrates a T 1/2 fade rate of less than 200 seconds. Also provided is a photochromic article comprising a rigid substrate and a photochromic organic polymeric coating applied to a surface of the substrate. The photochromic organic polymeric coating comprises the composition described above.
1. A curable, organic polymeric photochromic composition comprising:
a) a photochromic amount of at least one photochromic material;
b) a polymeric polyol having carbonate groups along its backbone and having a number average molecular weight greater than 5000 g/mole, wherein the polymeric polyol has a polydispersity index less than or equal to 1.50; and
c) a curing agent having reactive functional groups capable of reacting with hydroxyl groups on the polymeric polyol b); wherein after curing and the Photochromic Performance Test, the composition demonstrates a T 1/2 fade rate of less than 90 seconds.
2. The composition of claim 1 , wherein the polymeric polyol has a number average molecular weight greater than 6000 g/mole up to and including 20,000 g/mole.
3. A photochromic article comprising:
(a) a rigid substrate,
(b) a photochromic organic polymeric coating applied to a surface of said substrate, said photochromic coating comprising:
i) a photochromic amount of at least one photochromic material;
ii) a polymeric polyol having carbonate groups along its backbone and having a number average molecular weight greater than 5000 g/mole, wherein the polymeric polyol has a polydispersity index less than or equal to 1.50; and
iii) a curing agent having reactive functional groups capable of reacting with hydroxyl groups on the polymeric polyol b); wherein after application of the coating to the substrate, after curing, and after the Photochromic Performance Test, the composition demonstrates a T 1/2 fade rate of less than 90 seconds.
4. The article of claim 3 , wherein the polymeric polyol has a number average molecular weight greater than 6000 g/mole up to and including 20,000 g/mole.
5. The article of claim 3 , wherein the rigid substrate is an organic polymeric substrate chosen from thermoset or thermoplastic materials having a refractive index of at least 1.48.
6. The article of claim 5 , wherein the organic polymeric substrate comprises a thermoset substrate prepared from polymerizable compositions comprising allyl diglycol carbonate monomer(s), a substrate prepared from thermoplastic polycarbonates, a substrate prepared from polyurea urethanes or a substrate prepared from compositions comprising the reaction product of polyfunctional isocyanate(s) and/or isothiocyanate(s) with polythiol(s) or polyepisulfide monomer(s).
7. The article of claim 6 , wherein the thermoset substrate is diethylene glycol bis(allyl carbonate).
8. The article of claim 3 , wherein the photochromic material is an organic photochromic material comprising photochromic spirooxazines, benzopyrans, naphthopyrans, fulgides, metal dithizonates, diarylethenes or mixtures of such photochromic materials.
9. The article of claim 8 , wherein the photochromic material is a naphthopyran comprising naphtho[1,2-b]pyrans, naphtho[2,1-b]pyrans, spiro-9-fluoreno[1,2-b]pyrans, phenanthropyrans, quinopyrans and/or indeno-fused naphthopyrans.
10. The article of claim 8 , wherein the photochromic material is a spirooxazine comprising naphthoxazines and/or spiro(indoline)pyridobenzoxazines.
11. The article of claim 3 , wherein the article is a lens.