POLYMERIZABLE PHOTOCHROMIC COMPOSITIONS WITH MULTIPLE INITIATORS

• US 20070257238A1
• Filed: 04/05/2007
• Published: 11/08/2007
• Est. Priority Date: 05/05/2006
• Status: Abandoned Application

• Current Assignee: Transitions Optical, Inc. (EssilorLuxottica SA)
• Original Assignee: Transitions Optical, Inc. (EssilorLuxottica SA)
• Inventors: Stewart, Kevin, Misura, Michael
• Application Number:
  US11/696,895
• Publication Number:
  US 20070257238A1
• Time in Patent Office: Days
• US Class Current: 252/586
• CPC Class Codes: C08F 4/38 Mixtures of peroxy-compounds
• CPC Class Codes: C09K 2211/14 Macromolecular compounds
• CPC Class Codes: C09K 9/02 Organic tenebrescent materials

Abstract

Provided is a method of preparing a photochromic polymeric article including: (a) providing a fluid polymerizable composition of: at least one monomer; a first initiator for inducing polymerization of the monomer at a first temperature; and a second initiator for inducing further polymerization at a second temperature higher than the first temperature; (b) heating the polymerizable composition to at least the first temperature whereby the first initiator induces polymerization of the monomer at the first temperature to produce a polymerizate; (c) heating the polymerizate of (b) to at least the second temperature to further polymerize the polymerizate; and (d) contacting the polymerizate with an organic photochromic substance to incorporate the organic photochromic substance into the polymerizate. Photochromic articles prepared by the method are also provided.

Claims

1. A method of preparing a photochromic polymeric article comprising:

(a) providing a fluid polymerizable composition comprising a mixture of;

at least one monomer;

a first initiator for inducing polymerization of the monomer at a first temperature; and

a second initiator for inducing further polymerization at a second temperature higher than the first temperature;

(b) heating the polymerizable composition to at least the first temperature whereby the first initiator induces polymerization of the monomer at the first temperature to produce a polymerizate;

(c) heating the polymerizate of (b) to at least the second temperature to further polymerize the polymerizate; and

(d) contacting the polymerizate with an organic photochromic substance to incorporate the organic photochromic substance into the polymerizate.

2. The method of claim 1 wherein the polymerizate produced in step (b) has a Barcol hardness of 50 to 70.

3. The method of claim 1 wherein the polymerizate procedure in step (b) has a double bond conversion of 75 to 90% of the double bonds in the fluid polymerizable composition.

4. The method of claim 1 wherein in (c), the polymerizate is contacted with a stabilizer composition.

5. The method of claim 4 wherein the stabilizer composition comprises a hindered amine light stabilizer.

6. The method of claim 1 wherein the first initiator comprises diisopropyl peroxydicarbonate, di(n-propylperoxydicarbonate, di(sec-butyl)peroxydicarbonate, di(2-ethylhexyl)peroxydicarbonate, 1,1-dimethyl-3-hydoxybutylperoxyneodecanoate, a-cumylperoxynecodecanoate, t-amylperoxyneodecanoate and/or t-butylperoxyneodecanoate.

7. The method of claim 1 wherein the second initiator is selected from the group consisting of t-butylperoxy 2-ethylhexyl carbonate, OO-t-butyl O-isopropyl monoperoxycarbonate, OO-t-amyl-O-(2-ethylhexyl)monoperoxycarbonate, t-butylperbenzoate, and/or t-amylperbenzoate.

10. A photochromic article produced according to the method of claim 1.

8. A method of preparing a photochromic polymeric article comprising:

(a) providing a fluid polymerizable composition comprising a monomer;

curing the polymerizable composition to produce a polymerizate having a double bond conversion of 80 to 90% of the double bond in the fluid polymerizable composition;

(b) contacting a surface of the polymerizate with a stabilizer composition;

(c) contacting said surface of the polymerizate with a photochromic composition; and

(d) curing said surface of the polymerizate.

9. The method of claim 8 wherein the polymerizable composition comprises a first initiator for polymerizing the monomer at a first temperature, and a second initiator for polymerizing the monomer at a second temperature higher than the first temperature, said curing step (b) comprising heating the polymerizable composition to at least the first temperature to polymerize the monomer.

11. A photochromic article produced according to the method of claim 8.