Polymerizable composition for optical material, optical material obtained from same composition, and plastic lens

Patent metadata

Field	Value
Publication number	US-9778396-B2
Application number	US-201314406963-A
Country	US
Kind code	B2
Filing date	Jun 19, 2013
Priority date	Jun 26, 2012
Publication date	Oct 3, 2017
Grant date	Oct 3, 2017

Abstract

A polymerizable composition for an optical material includes (A) one or more isocyanate compounds selected from aliphatic isocyanate compounds and alicyclic isocyanate compounds, (B) an active hydrogen compound having two or more functional groups, and (C) a photochromic compound.

First claim

The invention claimed is:

1. A polymerizable composition for an optical material comprising:
(A) one or more isocyanate compounds selected from aliphatic isocyanate compounds and alicyclic isocyanate compounds;
(B) an active hydrogen compound having two or more functional groups; and
(C) a photochromic compound,
wherein the isocyanate compound (A) is one or more selected from the group consisting of 1,6-hexamethylene diisocyanate, 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, isophorone diisocyanate, and compounds represented by the following formula (1)

wherein in the formula (1), Q 1 and Q 2 may be identical or different and represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms; and X 1 and X 2 may be identical or different and represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and

wherein the photochromic compound (C) is represented by the following formula

2. The polymerizable composition for an optical material according to claim 1 ,
wherein the isocyanate compound (A) includes the compounds represented by Formula (1).

3. The polymerizable composition for an optical material according to claim 1 ,
wherein the alicyclic isocyanate compound is bis(isocyanatocyclohexyl)methane.

4. The polymerizable composition for an optical material according to claim 1 ,
wherein the active hydrogen compound (B) is one or more selected from the group consisting of polyol compounds, polythiol compounds, and thiol compounds having a hydroxyl group.

5. The polymerizable composition for an optical material according to claim 1 ,
wherein the active hydrogen compound (B) is one or more selected from the group consisting of pentaerythritol tetrakis(2-mercaptoacetate), pentaerythritol tetrakis(3-mercaptopropionate), bis(mercaptoethyl) sulfide, 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 2,5-dimercapto-1,4-dithiane, 1,1,3,3-tetrakis(mercaptomethylthio) propane, 4,6-bis(mercaptomethylthio)-1,3-dithiane, 2-(2,2-bis(mercaptomethylthio)ethyl)-1,3-dithietane, trimethylolpropane tris(3-mercaptopropionate), and compounds represented by Formula (2)

wherein a and b independently represent an integer of 1 to 4, and c represents an integer of 1 to 3; Z is hydrogen or a methyl group, and in the case in which a plurality of Zs are present, they may be identical or different.

6. An optical material comprised of the polymerizable composition according to claim 1 .

7. A plastic lens including a base material comprised of the polymerizable composition according to claim 1 .

8. A method for manufacturing a plastic lens comprising:
a step of mixing (A) one or more isocyanate compounds selected from aliphatic isocyanate compounds and alicyclic isocyanate compounds, (B) an active hydrogen compound having two or more functional groups, and (C) a photochromic compound in one batch to prepare a polymerizable composition for an optical material; and
a step of forming a lens base material by polymerizing the polymerizable composition in a mold,
wherein the isocyanate compound (A) is one or more selected from the group consisting of 1,6-hexamethylene diisocyanate, 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, isophorone diisocyanate, and compounds represented by the following formula (1)

wherein in the formula (1), Q 1 and Q 2 may be identical or different and represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms; and X 1 and X 2 may be identical or different and represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and

wherein the photochromic compound (C) is represented by the following formula (6),

Assignees

• Mitsui Chemicals Inc

Inventors

• Ryu Akinori

Classifications

• C09K9/02

  Organic tenebrescent materials · CPC title

• G02B1/041 Primary

  Lenses · CPC title

• G02C7/10

  Filters, e.g. for facilitating adaptation of the eyes to the dark; Sunglasses · CPC title

• C08G18/3876

  containing mercapto groups · CPC title

• C08G18/38

  having heteroatoms other than oxygen (C08G18/32 takes precedence) · CPC title