Photochromic curable composition

• US 9,588,257 B2
• Filed: 07/10/2012
• Issued: 03/07/2017
• Est. Priority Date: 07/11/2011
• Status: Active Grant

• Current Assignee: Tokuyama Corporation
• Original Assignee: Tokuyama Corporation
• Inventors: Otani, Toshiaki, Takenaka, Junji, Momoda, Junji, Izumi, Shinobu
• Primary Examiner(s): Ahvazi, Bijan
• Application Number:
  US14/129,822
• Publication Number:
  US 20140146285A1
• Time in Patent Office: 1,701 Days
• Field of Search: 252/586, 351/159.61, 351/163, 522/71, 523/105, 523/107, 427/162
• US Class Current: 1/1
• CPC Class Codes: C08F 2/44 Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
• CPC Class Codes: C08F 2/46 Polymerisation initiated by wave energy or particle radiation
• CPC Class Codes: C08F 222/102 of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
• CPC Class Codes: C08F 222/1025 of aromatic dialcohols
• CPC Class Codes: C08F 230/08 containing silicon
• CPC Class Codes: C08F 230/085 the monomer being a polymerisable silane, e.g. (meth)acryloyloxy trialkoxy silanes or vinyl trialkoxysilanes
• CPC Class Codes: C08F 290/06 Polymers provided for in subclass C08G
• CPC Class Codes: C08G 65/3322 acyclic
• CPC Class Codes: C08G 77/14 containing silicon bound to oxygen-containing groups C08G77/045 takes precedence
• CPC Class Codes: C08G 77/20 containing silicon bound to unsaturated aliphatic groups C08G77/045 takes precedence
• CPC Class Codes: C08G 77/442 containing vinyl polymer sequences
• CPC Class Codes: C08G 77/46 containing polyether sequences
• CPC Class Codes: C08L 83/12 containing polyether sequences
• CPC Class Codes: C09D 133/06 of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
• CPC Class Codes: C09D 171/02 Polyalkylene oxides
• CPC Class Codes: C09D 183/12 containing polyether sequences
• CPC Class Codes: C09D 4/00 Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
• CPC Class Codes: C09D 5/29 for multicolour effects
• CPC Class Codes: G02B 1/041 Lenses
• CPC Class Codes: G02B 1/10 Optical coatings produced by application to, or surface treatment of, optical elements G02B1/08 takes precedence
• CPC Class Codes: G02B 5/23 : Photochromic filters
• CPC Class Codes: G02C 7/102 : Photochromic filters

Abstract

A photochromic curable composition comprising, as radically polymerizable component (A), a silsesquioxane component (A1) having a radically polymerizable group and a bifunctional radically polymerizable monomer (A2) represented by the following general formula (1),

• • wherein a is a number of 0 to 30, and b is a number of 0 to 30 on condition that an average value of a+b is 2 to 30,
  • R¹, R², R³ and R⁴ are each a hydrogen atom or a methyl group, and
  • A is a divalent organic group on condition that the number of carbon atoms is 1 to 20, and a photochromic compound (B).

Claims

1. A photochromic coating agent comprising a photochromic curable composition which includes:

as radically polymerizable component (A), a silsesquioxane component (A1) having a radically polymerizable group and a bifunctional radically polymerizable monomer (A2), and a photochromic compound (B);

said silsesquioxane component (A1) being contained in an amount of 1 to 150 parts by mass per 100 parts by mass of the bifunctional radically polymerizable monomer (A2);

said silsesquioxane component (A1) having a weight average molecular weight of 2,000 to 10,000 and containing said radically polymerizable groups in a number at a ratio of 70 to 100% per the total number of substituents bonded to the silicon atoms; and

said bifunctional radically polymerizable monomer (A2) being represented by the following general formula (1);

2. The photochromic coating agent according to claim 1, wherein said silsesquioxane component (A1) contains a silsesquioxane that has a cage structure.

3. The photochromic coating agent according to claim 1, wherein said bifunctional radically polymerizable monomer (A2) contains a long-chain bifunctional radically polymerizable monomer (A2′

) having an average value a+b of 6 to 30 in the above general formula (1).

4. The photochromic coating agent according to claim 3, wherein said long-chain bifunctional radically polymerizable monomer (A2′

) is a low-hardness monomer of which the homopolymer has an L-scale Rockwell hardness of not more than 40.

5. The photochromic coating agent according to claim 1, wherein said photochromic compound (B) is a compound having an indeno[2,1-f]naphtho[1,2-b]pyran skeleton.

6. The photochromic coating agent according to claim 1, wherein said photochromic compound (B) is contained in an amount of 0.01 to 20 parts by mass per 100 parts by mass of said radically polymerizable component (A).

7. The photochromic coating agent according to claim 1, further containing a photo polymerization initiator or a thermal polymerization initiator.

8. The photochromic coating agent according to claim 1, further containing other radically polymerizable monomer (A3) that corresponds to neither said silsesquioxane component (A1) nor said bifunctional radically polymerizable monomer (A2), the other radically polymerizable monomer (A3) being contained in an amount of 1 to 300 parts by mass per 100 parts by mass of said bifunctional radically polymerizable monomer (A2).

9. The photochromic coating agent according to claim 8, wherein the other radically polymerizable monomer (A3) contains a polyfunctional radically polymerizable monomer represented by the following general formula (2):

10. The photochromic coating agent according to claim 1 having a viscosity of 20 to 500 cps at 25°

C.

11. A photochromic lens having a photochromic coating obtained by curing the photochromic coating agent of claim 1 on a surface of a lens material.

12. The photochromic lens according to claim 11, wherein the photochromic coating has a thickness of 10 to 100 μ

m.