Photochromic Composition and Optical Article Using Photochromic Composition

• US 20140043586A1
• Filed: 04/16/2012
• Published: 02/13/2014
• Est. Priority Date: 04/18/2011
• Status: Active Grant

• Current Assignee: Tokuyama Corporation
• Original Assignee: Tokuyama Corporation
• Inventors: Hiraren, Toshimitsu, Mori, Katsuhiro, Shimizu, Yasutomo
• Granted Patent: US 9,513,407 B2
• Time in Patent Office: Days
• US Class Current: 351/159.61
• CPC Class Codes: C08G 18/0809 containing cationic or cationogenic groups
• CPC Class Codes: C08G 18/0823 containing carboxylate salt groups or groups forming them
• CPC Class Codes: C08G 18/10 Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
• CPC Class Codes: C08G 18/12 using two or more compounds having active hydrogen in the first polymerisation step
• CPC Class Codes: C08K 5/0041 Optical brightening agents, organic pigments
• CPC Class Codes: C09K 2211/1007 Non-condensed systems
• CPC Class Codes: C09K 2211/1011 Condensed systems
• CPC Class Codes: C09K 2211/1029 containing one nitrogen atom as the heteroatom
• CPC Class Codes: C09K 2211/1033 with oxygen
• CPC Class Codes: C09K 2211/1088 containing oxygen as the only heteroatom
• CPC Class Codes: C09K 9/02 Organic tenebrescent materials
• CPC Class Codes: G02B 1/041 Lenses
• CPC Class Codes: G02B 5/23 Photochromic filters
• CPC Class Codes: G02C 7/102 Photochromic filters
• CPC Class Codes: G02F 2202/14 photochromic
• CPC Class Codes: Y10T 156/10 Methods of surface bonding and/or assembly therefor

Abstract

To provide a photochromic composition which functions as an adhesive layer for bonding two optical sheets that are formed of a polycarbonate resin or the like, so that a laminate that is obtained by bonding two optical sheets with the composition being sandwiched therebetween has excellent adhesion, heat resistance and photochromic properties. In particular, to provide a photochromic composition which is capable of forming an adhesive layer that is not decreased in the adhesion between the optical sheets even in cases where the adhesive layer is in contact with hot water. Provided is a photochromic composition which contains a urethane polymer having a polymerizable group (component A) and a photochromic compound (component B).

Claims

1. A photochromic composition comprising an urethane polymer (A) having polymerizable group within a molecule, a photochromic compound (B), and a monomer having a polymerizable group which is added depending on the needs, wherein

said polymerizable group is any one selected from the group consisting of silanol group or a group capable of forming a silanol group by hydrolysis, (meth)acrylate group, epoxy group, and vinyl group, and

a mol number of the polymerizable group per 100 gram of an entire component having the polymerizable group included in the photochromic composition is

(1) 10 mmol or more and 250 mmol or less, in case the polymerizable group is a silanol group or a group forming the silanol group by hydrolysis;

(2) 10 mmol or more and 200 mmol or less, in case the polymerizable group is (meth)acrylate group, epoxy group, or vinyl group.

2. The photochromic composition as set forth in claim 1 wherein said urethane polymer (A) is a prepolymer obtained by reacting;

a polyol compound (A1) of a number average molecular weight of 400 to 3000 having two or more of hydroxyl groups within a molecule,

a polyisocyanate compound (A2) having two or more isocyanate groups within a molecule,

a chain extender (A3) of a molecular weight of 50 to 300 having two or more groups capable of reacting with isocyanate group in a molecule, and

a compound (A4) having one or two groups capable of reacting with isocyanate group within a molecule and having said polymerizable group in the molecule.

3. The photochromic composition as set forth in claim 2 wherein an amount ratio of (A1) component, (A2) component, (A3) component, and (A4) component used for obtaining said urethane polymer (A) is n1:

n2;

n3;

n4=0.33 to 0.85;

1;

0.1 to 0.65;

0.01 to 0.3, and 0.9≦

n1+n3+n4≦

1.1 wherein;

a total mol number of the hydroxyl group included in said (A1) component is n1,

a total mol number of isocyanate group included in said (A2) component is n2,

a total mol number of a group capable of reacting with isocyanate group included in said (A3) component is n3, and

a total mol number of a group capable of reacting with isocyanate group included in said (A4) component is n4.

4. The photochromic composition as set forth in claim 1 further comprising a polymerization initiator.

5. The photochromic composition as set forth in claim 1 further comprising an isocyanate compound (C) having at least one isocyanate group within a molecule.

6. The photochromic composition as set forth in claim 5 wherein a molecular weight of said isocyanate compound (C) is 100 or more and less than 1000.

7. The photochromic composition as set forth in claim 1 further comprising an organic solvent (D).

8. The photochromic composition as set forth in claim 1 wherein 0.1 to 20 parts by mass of said photochromic compound (B) is included with respect to 100 parts by mass of said urethane polymer (A).

9. The photochromic composition as set forth in claim 1 wherein 0.1 to 20 parts by mass of said photochromic compound (B) and 0.1 to 30 parts by mass of monomer having the polymerizable group are included with respect to 100 parts by mass of said urethane polymer (A).

10. The photochromic composition as set forth in claim 5 further including 0.1 to 20 parts by mass of said isocyanate compound (C) with respect to 100 parts by mass of said urethane polymer (A).

11. The photochromic composition as set forth in claim 7 further including 5 to 900 parts by mass of the organic solvent (D) with respect to 100 parts by mass of said urethane polymer (A).

12. An optical article having a laminated structure by binding two optical sheets or optical films facing against each other via an adhesive layer obtained from the photochromic composition as set forth in claim 1.

13. The optical article as set forth in claim 12 wherein at least one of said two optical sheets or the optical films facing against each other in said laminated structure is made of polycarbonate resin.

14. A production method of the optical article as set forth in claim 12, comprising:

preparing a photochromic adhesive sheet comprising the urethane polymer (A), the photochromic compound (B), and the monomer having the polymerizable group blended depending on the needs, by removing the organic solvent (D) by drying after extending the photochromic composition as set forth in claim 7 on the flat and smooth base material, then further releasing the flat and smooth base material, and

making a laminated structure by polymerizing the polymerizable group after binding two optical sheets or the optical films by placing said photochromic adhesive sheet between the two optical sheets or the optical films facing against each other.