Plastic polarized lens, method for producing the same, and polarized film

1. A plastic polarized lens comprising:

a polarized film and

layers comprising a thiourethane-based resin stacked over both surfaces of the polarized film,

wherein the polarized film contains a dichroic dye and an organic coloring compound represented by the following general formula (1):

wherein A 1 to A 8 each independently represent a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydroxy group, an amino group, a carboxyl group, a sulfone group, a linear, branched, or cyclic alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, a monoalkylamino group having 1 to 20 carbon atoms, a dialkylamino group having 2 to 20 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, a heteroaryl group, an alkylthio group having 1 to 20 carbon atoms, or an arylthio group having 1 to 20 carbon atoms, or may form a ring other than an aromatic ring through a linking group, and M represents two hydrogen atoms, a divalent metal atom, a trivalent mono-substituted metal atom, a tetravalent di-substituted metal atom, or an oxy metal.

2. The plastic polarized lens according to claim 1 , wherein the organic coloring compound is represented by the following general formula (1 a):

wherein t-C 4 H 9 represents a tertiary butyl group, four tertiary butyl groups correspond to A 1 or A 2 , A 3 or A 4 , A 5 or A 6 , and A 7 or A 8 , respectively in the formula (1), and represent a position isomer structure, four groups that are not tertiary butyl groups in A 1 to A 8 represent a hydrogen atom; M represents a divalent copper atom, a divalent palladium atom, or divalent vanadium oxide (—V(═O)—).

3. The plastic polarized lens according to claim 1 , wherein the polarized film is comprised of a thermoplastic polyester.

4. The plastic polarized lens according to claim 3 , wherein the polarized film is shaped under the condition of the temperature T 1 represented by the following formula:

Glass transition temperature of the thermoplastic polyester+20° C.≦ T 1≦Glass transition temperature of the thermoplastic polyester+120° C.

5. The plastic polarized lens according to claim 3 , wherein the thermoplastic polyester is a polyethylene terephthalate.

6. The plastic polarized lens according to claim 1 , wherein the oranic coloring compound is contained in the amount of 50 to 7000 ppm and the dichroic dye is contained in the amount of 0.005 parts by weight to 4 parts by weight with respect to 100 parts by weight of the resin in the polarized film.

7. The plastic polarized lens according to claim 1 , wherein the thiourethane-based resin is obtained by reacting

(A) at least one kind of isocyanate compounds selected from the group consisting of a polyisocyanate compound, an isocyanate compound having an isothiocyanate group, and a polyisothiocyanate compound with

(B) at least one kind of active hydrogen compounds selected from the group consisting of thiol compounds and polythiol compounds having a hydroxy group.

8. The plastic polarized lens according to claim 7 , wherein the isocyanate compound (A) is a diisocyanate compound and the active hydrogen compound (B) is a polythiol compound.

9. The plastic polarized lens according to claim 7 , wherein the isocyanate compound (A) is at least one kind of diisocyanate compound selected from the group consisting of 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, and m-xylylene diisocyanate, and

the active hydrogen compound (B) is at least one kind of polythiol compound selected from the group consisting of pentaerythritoltetrakis(3-mercaptopropionate), 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, and 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane.

10. The plastic polarized lens according to claim 1 , further comprising the adhesive layer on at least one surface of the polarized film.

11. The plastic polarized lens according to claim 1 , wherein the refractive index at e-line of the thiourethane-based resin is in a range of 1.57 to 1.70.

12. The plastic polarized lens according to claim 1 , wherein the refractive index at e-line of the thiourethane-based resin is in a range of 1.59 to 1.70.

13. A method of producing a plastic polarized lens, comprising:

producing a resin film containing an organic coloring compound represented by the following general formula (1) and a dichroic dye;

shaping the resin film to obtain a polarized film;

fixing the polarized film in a lens casting mold in a state in which the polarized film is apart from the mold;

injecting a monomer mixture into the space between both surfaces of the polarized film and the mold; and

stacking layers comprising a thiourethane-based resin over both surfaces of the polarized film by polymerizing and curing the monomer mixture:

wherein A 1 to A 8 each independently represent a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydroxy group, an amino group, a carboxyl group, a sulfone group, a linear, branched, or cyclic alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, a monoalkylamino group having 1 to 20 carbon atoms, a dialkylamino group having 2 to 20 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, a heteroaryl group, an alkylthio group having 1 to 20 carbon atoms, or an arylthio group having 1 to 20 carbon atoms, or may form a ring other than an aromatic ring through a linking group, and M represents two hydrogen atoms, a divalent metal atom, a trivalent mono-substituted metal atom, a tetravalent di-substituted metal atom, or an oxy metal.

14. The method of producing a plastic polarized lens according to claim 13 , wherein the organic coloring compound is represented by the following general formula (1a):

wherein t-C 4 H 9 represents a tertiary butyl group, four tertiary butyl groups correspond to A 1 or A 2 , A 3 or A 4 , A 5 or A 6 , and A 7 or A 8 , respectively, in the formula (1), and represent a position isomer structure, four groups that are not tertiary butyl groups in A 1 to A 8 represent a hydrogen atom; M represents a divalent copper atom, a divalent palladium atom, or divalent vanadium oxide (—V(═O)—).

15. The method of producing a plastic polarized lens according to claim 13 , wherein the resin film is a thermoplastic polyester film.

16. The method of producing a plastic polarized lens according to claim 15 , wherein the step of shaping the resin film includes:

shaping the thermoplastic polyester film under the temperature condition of the glass transition temperature of the thermoplastic polyester+20° C. or higher and the glass transition temperature+120° C. or lower.

17. The method of producing a plastic polarized lens according to claim 15 , wherein the thermoplastic polyester is a polyethylene terephthalate.

18. The method of producing a plastic polarized lens according to claim 13 , wherein the monomer mixture includes:

(A) at least one kind of isocyanate compounds selected from the group consisting of a polyisocyanate compound, an isocyanate compound having an isothiocyanate group, and a polyisothiocyanate compound,

(B) at least one kind of active hydrogen compound selected from the group consisting of thiol compounds and polythiol compounds having a hydroxy group.

19. The method of producing a plastic polarized lens according to claim 18 , wherein the isocyanate compound (A) is a diisocyanate compound and the active hydrogen compound (B) is a polythiol compound.

20. The method of producing a plastic polarized lens according to claim 18 , wherein the isocyanate compound (A) is at least one kind of diisocyanate compounds selected from the group consisting of 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, and m-xylylene diisocyanate, and

the active hydrogen compound (B) is at least one kind of polythiol compounds selected from the group consisting of pentaerythritoltetrakis(3-mercaptopropionate), 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, and 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane.

21. The method of producing a plastic polarized lens according to claim 13 , further comprising:

subjecting at least one surface of the polarized film to a surface modification treatment before the fixing the polarized film.

22. The method of producing a plastic polarized lens according to claim 13 , further comprising:

forming an adhesive layer over at least one surface of the polarized film before the fixing the polarized film.

23. The method of producing a plastic polarized lens according to claim 13 , further comprising:

subjecting at least one surface of the polarized film to a surface modification treatment; and

forming an adhesive layer over the surface that has been subjected to a surface modification treatment,

before the fixing the polarized film.

24. The method of producing a plastic polarized lens according to claim 13 , wherein the viscosity at 20° C. of the monomer mixture is 200 mPa·s or less in the injecting step.

25. The method of producing a plastic polarized lens according to claim 13 , wherein the dichroic dye is represented by the following formulae (5) to (12):

26. A polarized film comprising a resin, a dichroic dye and an organic coloring compound represented by the following general formula (1):

wherein A 1 to A 8 each independently represent a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydroxy group, an amino group, a carboxyl group, a sulfone group, a linear, branched, or cyclic alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, a monoalkylamino group having 1 to 20 carbon atoms, a dialkylamino group having 2 to 20 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, a heteroaryl group, an alkylthio group having 1 to 20 carbon atoms, or an arylthio group having 1 to 20 carbon atoms, or may form a ring other than an aromatic ring through a linking group, and M represents two hydrogen atoms, a divalent metal atom, a trivalent mono-substituted metal atom, a tetravalent di-substituted metal atom, or an oxy metal.

27. The polarized film according to claim 26 , wherein the organic coloring compound is represented by the following general formula (1a):

wherein t-C 4 H 9 represents a tertiary butyl group, four tertiary butyl groups correspond to A 1 or A 2 , A 3 or A 4 , A 5 or A 6 , and A 7 or A 8 , respectively, in the formula (1), and represent a position isomer structure, four groups that are not tertiary butyl groups in A 1 to A 8 represent a hydrogen atom; M represents a divalent copper atom, a divalent palladium atom, or divalent vanadium oxide (—V(═O)—).

28. The polarized film according to claim 26 , wherein the resin is a thermoplastic polyester.

29. The polarized film according to claim 28 , wherein the thermoplastic polyester is a polyethylene terephthalate.

30. The polarized film according to claim 26 , wherein the organic coloring compound is contained in the amount of 50 to 7000 ppm and the dichroic dye is contained in the amount of 0.005 parts by weight to 4 parts by weight with respect to 100 parts by weight of the resin in the polarized film.

31. A method for producing the polarized film according to claim 26 , comprising:

producing a resin film containing the organic coloring compound and the dichroic dye; and

shaping the resin film.

32. The method for producing the polarized film according to claim 31 , wherein the resin film is a thermoplastic polyester film.

33. The method for producing the polarized film according to claim 32 , wherein shaping the resin film includes:

shaping the thermoplastic polyester film under the temperature condition of from the glass transition temperature of the thermoplastic polyester+20° C. to the glass transition temperature+120° C.

34. The method for producing the polarized film according to claim 31 , wherein the dichroic dye is represented by the following formulae (5) to (12):

35. The plastic polarized lens according to claim 1 , wherein the dichroic dye is represented by the following formulae (5) to (12):

36. The polarized film according to claim 26 , wherein the dichroic dye is represented by the following formulae (5) to (12):

37. The plastic polarized lens according to claim 1 , wherein at least one surface of the polarized film is surface modified.