Composite optical articles

• US 8,848,288 B2
• Filed: 03/02/2012
• Issued: 09/30/2014
• Est. Priority Date: 03/04/2011
• Status: Active Grant

• Current Assignee: PPG Industries Ohio Incorporated (Nouryon BV)
• Original Assignee: PPG Industries Ohio Incorporated (Nouryon BV)
• Inventors: Retsch, William H. Jr.
• Primary Examiner(s): Tran, Thao T.
• Application Number:
  US13/410,370
• Publication Number:
  US 20120224139A1
• Time in Patent Office: 942 Days
• Field of Search: 428/423.3, 428/213, 359/485.01, 359/489.14, 359/642, 528/59, 528/65
• US Class Current: 359/485.01
• CPC Class Codes: C08G 18/3234 cycloaliphatic
• CPC Class Codes: C08G 18/324 containing only one aromatic ring
• CPC Class Codes: C08G 18/3876 containing mercapto groups
• CPC Class Codes: C08G 18/722 Combination of two or more aliphatic and/or cycloaliphatic polyisocyanates
• CPC Class Codes: C08G 18/758 containing two or more cycloaliphatic rings
• CPC Class Codes: C08L 75/04 Polyurethanes
• CPC Class Codes: C08L 81/00 Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen or carbon only; Compositions of polysulfones; Compositions of derivatives of such polymers
• CPC Class Codes: G02B 1/041 Lenses
• CPC Class Codes: G02B 5/23 Photochromic filters
• CPC Class Codes: Y10T 428/2495 Thickness [relative or absolute]
• CPC Class Codes: Y10T 428/31554 Next to second layer of polyamidoester

Abstract

Provided is a composite optical article including (a) a polymeric base layer comprising a sulfur-containing urethane-based material having a refractive index of at least 1.57; and (b) a polymeric outer layer cast over a surface of the base layer (a) comprising (i) a poly(urea-urethane) material having a refractive index of less than 1.57, and (ii) a photochromic compound and/or a static dye. The thickness of the base layer (a) is greater than the thickness of the outer layer (b).

Claims

1. A composite optical article comprising:

(a) a polymeric base layer comprising a sulfur-containing urethane-based material having a refractive index of at least 1.57, wherein the sulfur-containing urethane-based material comprises the reaction product of the following components;

(A) a polyisocyanate;

(B) a thioether-functional, oligomeric polythiol prepared by reacting together;

(1) a compound having at least two thiol functional groups;

(2) a compound having triple bond functionality; and

optionally,

(3) a compound having at least two double bonds; and

, optionally,

(C) a compound different from (B) containing active hydrogens; and

(b) a polymeric outer layer cast over a surface of the base layer (a) comprising

(i) a poly(urea-urethane) material having a refractive index of less than 1.57, and

(ii) a photochromic compound and/or a static dye,

wherein the thickness of the base layer (a) is greater than the thickness of the outer layer (b), and wherein the thickness of the outer layer (b) ranges from 0.5 millimeter to 1.0 millimeter.

2. The optical article of claim 1, wherein the base layer (a) has an optical power.

3. The optical article of claim 1, wherein the base layer (a) has a refractive index ranging from 1.57 to 1.70.

4. The optical article of claim 1, wherein the reactive compound (A) comprises a diisocyanate or a mixture of a diisocyanate and a polyisocyanate having more than two isocyanate functional groups.

5. The optical article of claim 1, wherein the compound (1) having at least two thiol functional groups comprises a dithiol, a compound having more than two thiol functional groups, or a mixture of a dithiol and a compound having more than two thiol functional groups.

6. The optical article of claim 1, wherein the compound (2) having triple bond functionality comprises propargyl alcohol, propargyl chloride, propargyl bromide, propargyl acetate, propargyl propionate, propargyl benzoate, phenyl acetylene, phenyl propargyl sulfide, 1,4-dichloro-2-butyne, 2-butyne-1,4-diol, 3-butyne-2-ol, 2-pentyne, 1-hexyne, 2-hexyne, 3-hexyne, 3-hexyne-2,5-diol, and/or mixtures thereof.

7. The optical article of claim 1, wherein the compound (3) having at least two double bonds is present and comprises acyclic non-conjugated dienes, acyclic polyvinyl ethers, allyl-(meth)acrylates vinyl-(meth)acrylates, di(meth)acrylate esters of diols, di(meth)acrylate esters of dithiols, di(meth)acrylate esters of poly(alkyleneglycol) diols, monocyclic non-aromatic dienes, polycyclic non-aromatic dienes, aromatic ring-containing dienes, diallyl esters of aromatic ring dicarboxylic acids, and/or divinyl esters of aromatic ring dicarboxylic acids.

8. The optical article of claim 1, wherein the compound (C) is present and comprises a compound having at least two active hydrogen-containing groups comprising primary amine groups, secondary amine groups, hydroxyl groups, and/or thiol groups.

9. The optical article of claim 1, wherein the outer layer (b) has a refractive index ranging from 1.50 to 1.55.

10. The optical article of claim 1, wherein the outer layer (b) comprises the reaction product of:

(a) a prepolymer having isocyanate functional groups comprising the reaction product of;

(i) at least one polyol; and

(ii) at least one polyisocyanate; and

(b) at least one polyamine, wherein the number of isocyanato groups of the polyisocyanate reactants is greater than the number of hydroxyl groups of the polyol reactants.

11. The optical article of claim 10, wherein the polyol (i) is selected from simple diols, ester diols, polyester diols, polyether diols, or mixtures thereof.

12. The optical article of claim 11, wherein the polyol (i) comprises a polyester diol comprised of poly(caprolactone diol).

13. The optical article of claim 10, wherein the polyamine (b) is selected from the group consisting of aliphatic polyamines, alicyclic polyamines, aromatic polyamines, and mixtures thereof.

14. The optical article of claim 1, wherein the photochromic compound (ii) is present and comprises an organic photochromic material selected from the group consisting of pyrans, oxazines, fulgides, fulgimides, diarylethenes, and mixtures thereof.

15. The optical article of claim 1, further comprising a polarizer disposed between the base layer (a) and the outer layer (b).

16. The optical article of claim 1 which is a lens.

17. The optical article of claim 16 which is an ophthalmic lens.