Photocromic composition

Patent metadata

Field	Value
Publication number	US-9377664-B2
Application number	US-201214111393-A
Country	US
Kind code	B2
Filing date	Apr 12, 2012
Priority date	Apr 13, 2011
Publication date	Jun 28, 2016
Grant date	Jun 28, 2016

Abstract

Provided is a photochromic composition which can function as an adhesive layer for bonding optical sheets made from a polycarbonate resin or the like and a laminated article using said composition exhibits excellent tight adhesion, heat resistance and photochromic properties. In particular, provided is a photochromic composition which can prevent an elution of the composition from the optical sheets when embedding and polymerizing in a polymerizable monomer. The photochromic composition comprises a polyurethane resin (A) having an isocyanurate structure and a photochromic compound (B).

First claim

The invention claimed is:

1. An optical article having a multilayer structure wherein two optical sheets or optical films facing each other are bound via an adhesive layer comprising a photochromic composition comprising a polyurethane resin (A) having an isocyanurate structure and a photochromic compound (B), wherein said polyurethane resin (A) having the isocyanurate structure is the polyurethane resin obtained by reacting,
a polyol compound (A1) having two or more hydroxyl groups in the molecule, and having a number-average molecular weight of 400 to 3,000,
an isocyanurate compound (A2a) having an isocyanurate structure and three isocyanate groups in the molecule,
a diisocyanate compound (A2b) having two isocyanate groups in the molecule, and
a chain extender (A3) having two or more groups capable of reacting with the isocyanate groups in the molecule, and having a molecular weight of 50 to 300.

2. The optical article as set forth in claim 1 , having the multilayer structure wherein at least one of the two optical sheets or optical films facing each other is made of polycarbonate resin.

3. A production method of the optical article as set forth in claim 1 , comprising:
a step of preparing a photochromic adhesive sheet comprising the polyurethane resin (A) having the isocyanurate structure and the photochromic compound (B), by extending a photochromic composition comprising a polyurethane resin (A) having an isocyanurate structure, a photochromic compound (B), and an organic solvent (D), wherein said polyurethane resin (A) having the isocyanurate structure is the polyurethane resin obtained by reacting,
a polyol compound (A1) having two or more hydroxyl groups in the molecule, and having a number-average molecular weight of 400 to 3,000,
an isocyanurate compound (A2a) having an isocyanurate structure and three isocyanate groups in the molecule,
a diisocyanate compound (A2b) having two isocyanate groups in the molecule, and
a chain extender (A3) having two or more groups capable of reacting with the isocyanate groups in the molecule, and having a molecular weight of 50 to 300 on a flat and smooth base material, then removing the organic solvent (D) by drying and separating said flat and smooth base material; and
a step of forming said multilayer structure by binding the two optical sheets or optical films by placing said photochromic adhesive sheet in between the two optical sheets or optical films facing each other.

4. The optical article as set forth in claim 1 , wherein an amount ratio of the components (A1), (A2a), (A2b) and (A3) used when obtaining the polyurethane resin (A) having the isocyanurate structure satisfies n1:n2a:n2b:n3=0.30 to 0.90:0.01 to 0.50:0.50 to 0.99:0.10 to 0.70, wherein n2a+n2b=1 and 0.9≦n1+n3≦1.1, when a total mol number of a hydroxyl group included in said component (A1) is n1, a total mol number of an isocyanate group included in said component (A2a) is n2a, a total mol number of the isocyanate group included in said component (A2b) is n2b, and a total mol number of a group capable of reacting with the isocyanate group included in said component (A3) is n3.

5. The optical article as set forth in claim 1 , wherein the polyurethane resin (A) having the isocyanurate structure is a non-reactive polyurethane resin, to which a reaction terminator (A4), having one group capable of reacting with the isocyanate group, is bound to a terminal end of the molecule.

6. The optical article as set forth in claim 5 , wherein an amount ratio of the components (A1), (A2a), (A2b), (A3) and (A4) used when obtaining the non-reactive polyurethane resin satisfies n1:n2a:n2b:n3:n4=0.30 to 0.89:0.01 to 0.50:0.50 to 0.99:0.10 to 0.69:0.01 to 0.20, wherein n2a n2b=1 and 0.9≦n1+n3+n4≦1.1, when a total mol number of the hydroxyl group included in said component (A1) is n1, a total mol number of the isocyanate group included in said component (A2a) is n2a, a total mol number of the isocyanate group included in said component (A2b) is n2b, a total mol number of a group capable of reacting with the isocyanate group included in said component (A3) is n3, and a total mol number of the group capable of reacting with the isocyanate group included in said component (A4) is n4.

7. The optical article as set forth in claim 1 , wherein 30 mass % or more of a total amount of said isocyanurate compound (A2a) and said diisocyanate compound (A2b) is at least one isocyanate compound selected from the group consisting of aliphatic isocyanate compounds and alicyclic isocyanate compounds.

8. The optical article as set forth in claim 1 , wherein the photochromic composition further comprising an isocyanate compound (C) having at least one isocyanate group in the molecule.

9. The optical article as set forth in claim 8 , wherein a molecular weight of said isocyanate compound (C) is less than 1,000 and said isocyanate compound (C) is not a polymer.

10. The optical article as set forth in claim 1 , wherein the photochromic composition comprises 0.1 to 20 parts by mass of said photochromic compound (B) to 100 parts by mass of said polyurethane resin (A) having the isocyanurate structure.

11. The optical article as set forth in claim 1 , wherein the photochromic composition further comprises 0.01 to 20 parts by mass of an isocyanate compound (C) having at least one isocyanate group in the molecule to 100 parts by mass of said polyurethane resin (A) having the isocyanurate structure.

12. The production method as set forth in claim 3 , wherein the photochromic composition comprises 0.1 to 20 parts by mass of said photochromic compound (B) to 100 parts by mass of said polyurethane resin (A) having the isocyanurate structure.

13. The production method as set forth in claim 12 , wherein the photochromic composition further comprises 0.01 to 20 parts by mass of an isocyanate compound (C) having at least one isocyanate group in the molecule to 100 parts by mass of said polyurethane resin (A) having the isocyanurate structure.

14. The production method as set forth in claim 12 , wherein the photochromic composition further comprises 5 to 900 parts by mass of said organic solvent (D) to 100 parts by mass of said polyurethane resin (A) having the isocyanurate structure.

15. The production method as set forth in claim 12 , wherein the photochromic composition further comprises 0.01 to 20 parts by mass of an isocyanate compound (C) having at least one isocyanate group in the molecule and 5 to 900 parts by mass of said organic solvent (D) to 100 parts by mass of said polyurethane resin (A) having the isocyanurate structure.

Assignees

• Hiraren Toshimitsu
• Mori Katsuhiro
• Shimizu Yasutomo
• Tokuyama Corp

Inventors

• Hiraren Toshimitsu
• Mori Katsuhiro
• Shimizu Yasutomo

Classifications

• C09K2211/1033

  with oxygen · CPC title

• C08K5/1545

  Six-membered rings · CPC title

• C08K5/0041

  Optical brightening agents, organic pigments · CPC title

• C08G18/792

  formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates · CPC title

• C09K2211/1007

  Non-condensed systems · CPC title