Photochromic composition and optical article using photochromic composition

Patent metadata

Field	Value
Publication number	US-9513407-B2
Application number	US-201214112255-A
Country	US
Kind code	B2
Filing date	Apr 16, 2012
Priority date	Apr 18, 2011
Publication date	Dec 6, 2016
Grant date	Dec 6, 2016

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).

First claim

The invention claimed is:

1. A photochromic composition, comprising:
an urethane polymer (A) having a polymerizable group within a molecule,
a photochromic compound (B),
an isocyanate compound (C) having at least one isocyanate group within a molecule, and
an optional monomer having the polymerizable group,
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) being a polymerizable group imparting compound which can introduce the polymerizable group at the end terminal of said urethane polymer (A),
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,
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 n1+n3+n4=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, and
wherein a mol number of the polymerizable group per 100 gram of a total of said urethane polymer (A) and said optional monomer 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 further comprising a polymerization initiator.

3. The photochromic composition as set forth in claim 1 wherein a molecular weight of said isocyanate compound (C) is 100 or more and less than 1000.

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

5. 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).

6. 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).

7. The photochromic composition as set forth in claim 1 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).

8. The photochromic composition as set forth in claim 4 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).

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

10. The optical article as set forth in claim 9 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.

11. A production method of a photochromic laminated sheet, comprising:
preparing a photochromic adhesive sheet comprising the urethane polymer (A), the photochromic compound (B), and the optional monomer having the polymerizable group blended, by removing the organic solvent (D) by drying after extending the photochromic composition as set forth in claim 4 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.

12. A photochromic laminated sheet, comprising:
two optical sheets or optical films facing each other;
an adhesive layer comprising the photochromic composition as set forth in claim 1 between the two optical sheets or optical films, thereby binding the two optical sheets or optical films and forming a laminate structure.

13. A production method of a photochromic laminated sheet, comprising:
(1) preparing a photochromic adhesive sheet comprising:
applying the photochromic composition as set forth in claim 4 on a flat and smooth base material,
drying to remove the organic solvent; and
releasing the base material;

(2) placing the adhesive sheet between two optical sheets or optical films facing each other, thereby binding the two optical sheets or optical films; and
(3) polymerizing the polymerizable group, thereby making a laminated structure.

Assignees

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

Inventors

• Hiraren Toshimitsu
• Mori Katsuhiro
• Shimizu Yasutomo

Classifications

• C09K2211/1088

  containing oxygen as the only heteroatom · CPC title

• C09K2211/1033

  with oxygen · CPC title

• C08G18/12

  using two or more compounds having active hydrogen in the first polymerisation step · CPC title

• Y10T156/10

  Methods of surface bonding and/or assembly therefor · CPC title

• C09K2211/1007

  Non-condensed systems · CPC title