Plastic polarized lens and method of producing the same

Abstract

A plastic polarized lens of the present invention, comprising: a polarized film containing thermoplastic polyester, a coat layer containing a urethane-based resin comprised of a structural unit derived from compound having hydroxyl group and a structural unit derived from aromatic diisocyanate, which is formed over at least one surface of the polarized film and a substrate layer containing a thiourethane-based resin, which is formed over at least the coat layer of the coat layer-attached polarized film.

What is claimed is: 
     
         1 . A plastic polarized lens, comprising:
 a polarized film containing thermoplastic polyester,   a coat layer containing a urethane-based resin comprised of a structural unit derived from compound having hydroxyl group and a structural unit derived from aromatic diisocyanate, which is formed over at least one surface of the polarized film and   a substrate layer containing a thiourethane-based resin, which is formed over at least the coat layer of the coat layer-attached polarized film.   
     
     
         2 . The plastic polarized lens according to  claim 1 ,
 wherein, the compound having hydroxyl group is a trimethylolpropane and the aromatic diisocyanate is a tolylene diisocyanate.   
     
     
         3 . The plastic polarized lens according to  claim 2 ,
 wherein the coat layer further contains a silane coupling agent.   
     
     
         4 . The plastic polarized lens according to  claim 1 ,
 wherein, the compound having hydroxyl group is a polybutadiene having a hydroxyl group on the terminal and the aromatic diisocyanate is a diphenylmethane diisocyanate.   
     
     
         5 . The plastic polarized lens according to  claim 1 ,
 wherein the coat layer and the substrate layer are stacked in order over both surfaces of the polarized film.   
     
     
         6 . The plastic polarized lens according to  claim 1 ,
 wherein the thiourethane-based resin is obtained by reacting isocyanate compound(s) (A) with active hydrogen compound(s) (B) and   wherein the isocyanate compound(s) (A) is at lease one selected from a group consisting of a polyisocyanate compound, an isocyanate compound having an isothiocyanate group and a polyisothiocyanate, and the active hydrogen compound(s) (B) is at least one selected from a group consisting of a thiol compound having a hydroxyl group and a polythiol compound.   
     
     
         7 . The plastic polarized lens according to  claim 1 ,
 wherein the polarized film is shaped under a condition of a temperature T represented by the following formula,
   glass transition temperature of thermoplastic polyester+5° C.≦T≦melting point of thermoplastic polyester.  (Formula)
 
   
     
     
         8 . The plastic polarized lens according to  claim 1 ,
 wherein the polarized film is a polyethylene terephthalate film.   
     
     
         9 . The plastic polarized lens according to  claim 6 ,
 wherein the isocyanate compound(s) (A) is at least one of diisocyanate compounds selected from a group consisting of m-xylylene diisocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, 4,4′-diphenylmethane diisocyanate, 2,5-bis(isocyanatomethyl)-bicyclo[2.2.1]-heptane, 2,6-bis(isocyanatomethyl)-bicyclo[2.2.1]-heptane, bis(4-isocyanatocyclohexyl)methane, 1,3-bis(isocyanatomethyl)cyclohexane, 1,4-bis(isocyanatomethyl)cyclohexane, and hexamethylene diisocyanate, and   the active hydrogen compound(s) (B) is at least one of polythiol compounds selected from a group consisting of pentaerythritol tetrakis(3-mercaptopropionate), 5,7-dimercaptomethyl-1,1′-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,8-dimercaptomethyl-1,1′-dimercapto-3,6,9-trithiaundecane, 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 2,5-dimercaptomethyl-1,4-dithiane, 1,1,3,3-tetrakis(mercaptomethylthio)propane, 4,6-bis(mercaptomethylthio)-1,3-dithiane, and 2-(2,2-bis(mercaptomethylthio)ethyl)-1,3-dithietane.   
     
     
         10 . The plastic polarized lens according to  claim 2 ,
 wherein a refractive index at e-line of the thiourethane-based resin is in a range of 1.50 to 1.70.   
     
     
         11 . A method of producing a plastic polarized lens, comprising:
 forming a coat layer containing a urethane-based resin comprised of a structural unit derived from compound having hydroxyl group and a structural unit derived from aromatic diisocyanate, over at least one surface of a polarized film containing thermoplastic polyester;   fixing the coat layer-attached polarized film into a lens casting mold, in a state separated from an inner surface of the mold;   injecting a monomer mixture into a gap between at least the coat layer of the coat layer-attached polarized film and the inner surface of the mold; and   stacking a substrate layer containing a thiourethane-based resin over at least the coat layer of the coat layer-attached polarized film by polymerizing and curing the monomer mixture.   
     
     
         12 . The method of producing a plastic polarized lens according to  claim 11 ,
 wherein, the compound having hydroxyl group is a trimethylolpropane and the aromatic diisocyanate is a tolylene diisocyanate.   
     
     
         13 . The method of producing a plastic polarized lens according to  claim 12 ,
 wherein the coat layer further contains a silane coupling agent.   
     
     
         14 . The method of producing a plastic polarized lens according to  claim 11 ,
 wherein, the compound having hydroxyl group is a polybutadiene having a hydroxyl group on the terminal and the aromatic diisocyanate is a diphenylmethane diisocyanate.   
     
     
         15 . The method of producing a plastic polarized lens according to  claim 11 ,
 wherein the forming a coat layer includes forming the coat layer over both surfaces of the polarized film.   
     
     
         16 . The method of producing a plastic polarized lens according to  claim 11 , further comprising:
 shaping the polarized film under a condition of a temperature equal to or higher than a glass transition temperature of thermoplastic polyester +5° C. and equal to or lower than a melting point of thermoplastic polyester, before the forming a coat layer.   
     
     
         17 . The method of producing a plastic polarized lens according to  claim 12 , further comprising:
 a step of shaping the polarized film under a condition of a temperature equal to or higher than a glass transition temperature of thermoplastic polyester +5° C. and equal to or lower than a melting point of thermoplastic polyester, after the forming a coat layer.   
     
     
         18 . The method of producing a plastic polarized lens according to  claim 12 ,
 wherein, in the injecting a monomer mixture, a viscosity at 20° C. of the monomer mixture is not more than 200 mPa·s.   
     
     
         19 . A urethane-based resin-coated polarized film comprising:
 a polarized film containing thermoplastic polyester and   a coat layer containing a urethane-based resin comprised of a structural unit derived from compound having hydroxyl group and a structural unit derived from aromatic diisocyanate, which is formed over at least one surface of the polarized film.   
     
     
         20 . The urethane-based resin-coated polarized film according to  claim 19 ,
 wherein, the compound having hydroxyl group is a trimethylolpropane and the aromatic diisocyanate is a tolylene diisocyanate.   
     
     
         21 . The urethane-based resin-coated polarized film according to  claim 20 ,
 wherein the coat layer further contains a silane coupling agent.   
     
     
         22 . The urethane-based resin-coated polarized film according to  claim 19 ,
 wherein, the compound having hydroxyl group is a polybutadiene having a hydroxyl group on the terminal and the aromatic diisocyanate is a diphenylmethane diisocyanate.   
     
     
         23 . A method of producing a urethane-based resin-coated polarized film, comprising:
 forming a coat layer containing a urethane-based resin comprised of a structural unit derived from compound having hydroxyl group and a structural unit derived from aromatic diisocyanate, over at least one surface of a polarized film containing thermoplastic polyester.   
     
     
         24 . The method of producing a urethane-based resin-coated polarized film according to  claim 23 ,
 wherein, the compound having hydroxyl group is a trimethylolpropane and the aromatic diisocyanate is a tolylene diisocyanate.   
     
     
         25 . The method of producing a urethane-based resin-coated polarized film according to  claim 24 ,
 wherein the coat layer further contains a silane coupling agent.   
     
     
         26 . The method of producing a urethane-based resin-coated polarized film according to  claim 23 ,
 wherein, the compound having hydroxyl group is a polybutadiene having a hydroxyl group on the terminal and the aromatic diisocyanate is a diphenylmethane diisocyanate.