Photochromic coating exhibiting improved performance and reduced yellowness
View Patent ↗An acrylate-based optical coating composition containing a blend of monomers, a metal salt, a Hindered Amine Light Stabilizer (HALS), an antioxidant (AO), an initiator and a photochromic dye. The initiator has a range of free radical energy that is below a predetermined level. The cure process is controlled by the catalyst and initiator in combination with the HALS and AO to avoid deleterious reactions that can increase yellowness. The composition is well suited to be applied to a lens and cured in the mold to form a coating with reduced yellowness having high adhesion and abrasion-resistant properties. A photochromic segmented bifocal lens is produced with low photochromic fatigue and favorable % T values.
1. A thermally curable photochromic coating composition comprising:
a mixture having two different classes of monomers, where the two classes of monomers are selected from the group consisting of: (a) monofunctional (meth)acrylate; (b) difunctional (meth)acrylate; (c) a combination of a monofunctional (meth)acrylate and a difunctional (meth)acrylate; (d) multifunctional (meth)acrylate; and (e) aliphatic urethane diacrylate;
a metal salt catalyst;
a Hindered Amine Light Stabilizer (HALS) selected from the group consisting of propanedioic acid [(4-(methoxyphenyl)-methylene]-bis(1,2,2,6,6-pentamethyl-4-piperidinyl) ester and phenyl-(3,5-di-tert.butyl-4-hydrox-benzyl)-malonic acid-bis-(1,2,2,6,6-penta-methyl-4-piperidinyl)ester;
an antioxidant;
an initiator; and
a photochromic dye.
2. The composition according to claim 1 , wherein the metal salt is selected from the group consisting of a metal ester of 2-naphthoic acid, a metal ester of 2-ethylhexanoic acid, a metal ester of octoate material, tin-2-ethylhexanoate, bismuth carboxylate, cobalt naphthenate and combinations thereof.
3. The composition according to claim 1 , wherein the HALS is phenyl-(3,5-di-tert.butyl-4-hydroxy-benzyl)-malonic acid-bis-(1,2,2,6,6-penta-methyl-4-piperidinyl)ester.
4. The composition according to claim 1 , wherein the antioxidant is a sterically hindered phenolic compound or a pentaerythritol tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate]hindered phenolic compound.
5. The composition according to claim 1 , wherein the initiator is selected from the group consisting of an organic peroxide which presents a free radical energy less than about 113 kcal/mol at 298 K, t-amylperoxy-2-ethylhexyl carbonate organic peroxide, and t-butylperoxy-2-ethylhexylcarbonate.
6. The composition according to claim 1 , wherein the monofunctional (meth)acrylate is selected from the group consisting of isobornylacrylate, hydroxypropylmethacrylate, benzyl acrylate and combinations thereof.
7. The composition according to claim 1 , wherein the difunctional (meth) acrylate is selected from the group consisting of polyethyleneglycol (600) dimethacrylate, ethoxylated (8) bisphenol A dimethacrylate, ethoxylated (10) bisphenol A diacrylate, and ethoxylated (30) bisphenol A dimethacrylate.
8. The composition according to claim 1 , wherein the multifunctional (meth)acrylate is selected from the group consisting of hexafunctional aliphatic urethane acrylate and dipentaerythritol pentaacrylate.
9. The composition according to claim 1 , wherein the aliphatic urethane diacrylate is selected from the group consisting of aliphatic polyester urethane diacrylate, aliphatic urethane diacrylate diluted with a reactive diluent 1,6-hexanediol diacrylate, aliphatic urethane diacrylate diluted with a reactive diluent isobornyl acrylate and combinations thereof.
10. A thermally curable photochromic coating composition comprising:
one or more monomers independently selected from the group consisting of (a) monofunctional (meth)acrylate; (b) difunctional (meth)acrylate; and (c) a combination of a monofunctional (meth)acrylate and a difunctional (meth)acrylate present in an amount from 10% to 25% by weight of the composition;
monomers of (d) multifunctional (meth)acrylate present in an amount from 20% to 40% by weight of the composition:
monomers of (e) aliphatic urethane diacrylate present in an amount from 50% to 70% by weight of the composition:
a metal salt present in an amount from 0.10 parts per hundred monomer (phm) to 0.30 phm;
a Hindered amine light stabilizer (FLALS) is present in an amount from 1.00 phm to 5.00 phm;
an antioxidant present in an amount from 0.20 phm to 0.50 phm;
an initiator present in an amount from 1.00 phm to 2.00 phm; and
a photochromic dye present in an amount from 1.00 phm. to 5.00 phm.
11. The composition according to claim 1 , wherein the monomer of (a) monofunctional (meth)acrylate comprises a mixture of isobornyl acrylate in an amount from 1% to 5% by weight of the composition and benzyl acrylate or 2-hydroxypropylmethacrylate in an amount from 10% to 21% by weight of the composition.
12. A thermaly curable photochromic coating composition comprising:
a mixture of monomers including isobornylacrylate present in an amount of 5% by weight of the composition, hydroxypropylmethamlate present in an amount of 10% by weight of the composition, aliphatic urethane diacrylate present in an amount of 18% by weight of the composition, hexafunctional aliphatic urethane acrylate present in an amount of 33% by weight of the composition, and aliphatic urethane diacrylate present in an amount of 34% by weight of the composition:
a metal salt including tin-2-ethythexanoate present in an amount of 0.14 phm;
a Hindered amine light stabilizer (HALS) including bis (1,2,2,6,6-pentamethyl-4-piperidinyl)-[[3,5-bis-(1,1-dimethylethyl)-4-hydroxyphenyl]methyl]butylmalonate or phenyl-(3,5-di-tert.butyl-4-hydroxy-benzyl)-malonic acid-Ns-(1,2,2,6,6-penta-methyl-4-piperidinyl)ester present in an amount of 1 part per hundred monomer (phm);
an antioxidant including pentaerythritol tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl) propionate]hindered phenolic compound present in an amount of 0.25 phm;
an initiator comprises including t-amylperoxy-2-ethylhexyl carbonate organic peroxide present in an amount of 1.5 phin; and
a photochromic dye present in an amount of 2.0 to 4.0 phm.
13. The composition according to claim 1 , further comprising a thermoplastic polyurethane (TPU) present in an amount from 0.5 parts per hundred monomer (phm) to 5.0 phm.
14. The composition according to claim 10 , further comprising a thermoplastic polyurethane (TPU) present in an amount from 0.5 parts per hundred monomer (phm) to 5.0phm.
15. The composition according to claim 12 , further comprising a thermoplastic polyurethane (TPU) present in an amount from 0.5 parts per hundred monomer (phm) to 5.0phm.