Optical material and use thereof

Patent metadata

Field	Value
Publication number	US-9857503-B2
Application number	US-201414917302-A
Country	US
Kind code	B2
Filing date	Sep 10, 2014
Priority date	Sep 10, 2013
Publication date	Jan 2, 2018
Grant date	Jan 2, 2018

Abstract

An optical material of the present invention has the following characteristics (1) to (4) in a transmittance curve which is measured at a thickness of 2 mm of the optical material.
(1) the transmittance curve has a maximum transmittance value at 400 nm to 440 nm and the maximum transmittance thereof is 50% or more. (2) the transmittance curve has a minimum transmittance value at 471 nm to 500 nm. (3) The transmittance at 540 nm is 60% or more. (4) The minimum transmittance value at 471 nm to 500 nm is seven-tenths or less of the maximum transmittance at 400 nm to 440 nm and is seven-tenths or less of the transmittance at 540 nm.

First claim

The invention claimed is:

1. An optical material comprising polythiourethane and 5 to 100 ppm of organic dye which is one or more compounds selected from porphyrin-based compounds represented by the following General Formula (A), in which a transmittance curve measured at a thickness of 2 mm thereof satisfies the following characteristics (1) to (4),
(1) the transmittance curve has a maximum transmittance value in a wavelength range of 400 nm to 440 nm and the maximum transmittance thereof is 50% or more,
(2) the transmittance curve has a minimum transmittance value in a wavelength range of 471 nm to 500 nm,
(3) the transmittance at a wavelength of 540 nm is 60% or more, and
(4) the minimum transmittance value in the wavelength range of 471 nm to 500 nm is seven-tenths or less of the maximum transmittance in the wavelength range of 400 nm to 440 nm and is seven-tenths or less of the transmittance at 540 nm,

wherein X 1 to X 8 each independently represent a hydrogen atom, a straight or branched alkyl group, an ethynyl group, an ethynyl group substituted with the straight or branched alkyl group, an ethynyl group having a phenyl group, or an ethynyl group having a phenyl group substituted with the straight or branched alkyl group; all of X 1 to X 8 are not hydrogen atoms at same time; R 1 to R 4 each independently represent a hydrogen atom, and a straight or branched alkyl group; and M represents two hydrogen atoms, a divalent metal atom, a trivalent substituted metal atom, a tetravalent substituted metal atom, a hydroxylated metal atom, or an oxidized metal atom.

2. The optical material according to claim 1 ,
wherein the minimum transmittance value in the wavelength range of 471 nm to 500 nm is 60% or less.

3. The optical material according to claim 1 ,
wherein the polythiourethane is comprised of a constituent unit derived from a polyisocyanate compound and a constituent unit derived from a polythiol compound,
wherein the polyisocyanate compound is at least one kind selected from 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, m-xylylene diisocyanate, dicyclohexylmethane diisocyanate, bis(isocyanatomethyl)cyclohexane, isophorone diisocyanate, 1,6-hexamethylene diisocyanate, and 1,5-pentamethylene diisocyanate, and
wherein the polythiol compound is at least one kind selected from 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, pentaerythritol tetrakis(3-mercaptopropionate), bis(mercaptoethyl)sulfide, pentaerythritol tetrakis(2-mercaptoacetate), 2,5-bis(mercaptomethyl)-1,4-dithiane, 1,1,3,3-tetrakis(mercaptomethylthio)propane, 4,6-bis(mercaptomethylthio)-1,3-dithiane, and 2-(2,2-bis(mercaptomethylthio)ethyl)-1,3-dithietane.

4. A plastic spectacle lens comprised of the optical material according to claim 1 .

5. A plastic spectacle lens,
wherein a lens base material is comprised of the optical material according to claim 1 .

6. The optical material according to claim 1 ,
wherein the amount of the organic dyes is 5 ppm to 50 ppm.

7. A composition for an optical material, comprising:
polythiourethane or a resin monomer wherein the resin monomer is a polyisocyanate compound and a polythiol compound; and
at least one kind of organic dye which is one or more compounds selected from porphyrin-based compounds represented by the following General Formula (A),
wherein the amount of the organic dye is 0.0005 parts by weight to 0.01 parts by weight with respect to 100 parts by weight in total of the polythiourethane or the resin monomer,

wherein X 1 to X 8 each independently represent a hydrogen atom, a straight or branched alkyl group, an ethynyl group, an ethynyl group substituted with the straight or branched alkyl group, an ethynyl group having a phenyl group, or an ethynyl group having a phenyl group substituted with the straight or branched alkyl group; all of X 1 to X 8 are not hydrogen atoms at same time; R 1 to R 4 each independently represent a hydrogen atom, and a straight or branched alkyl group; and M represents two hydrogen atoms, a divalent metal atom, a trivalent substituted metal atom, a tetravalent substituted metal atom, a hydroxylated metal atom, or an oxidized metal atom, and
wherein the optical material formed from the composition exhibits a transmittance curve measured at a thickness of 2 mm that satisfies the following characteristics (1) to
(1) the transmittance curve has a maximum transmittance value in a wavelength range of 400 nm to 440 nm and the maximum transmittance thereof is 50% or more,
(2) the transmittance curve has a minimum transmittance value in a wavelength range of 471 nm to 500 nm,
(3) the transmittance at a wavelength of 540 nm is 60% or more, and
(4) the minimum transmittance value in the wavelength range of 471 nm to 500 nm is seven-tenths or less of the maximum transmittance in the wavelength range of 400 nm to 440 nm and is seven-tenths or less of the transmittance at 540 nm.

8. The composition for an optical material according to claim 7 ,
wherein the polyisocyanate compound is at least one kind selected from 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, m-xylylene diisocyanate, dicyclohexylmethane diisocyanate, 1,3-bis(isocyanatomethyl)cyclohexane, 1,4-bis(isocyanatomethyl)cyclohexane, isophorone diisocyanate, 1,6-hexamethylene diisocyanate, and 1,5-pentamethylene diisocyanate, and
wherein the polythiol compound is at least one kind selected from 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, pentaerythritol tetrakis(3-mercaptopropionate), bis(mercaptoethyl)sulfide, pentaerythritol tetrakis(2-mercaptoacetate), 2,5-bis(mercaptomethyl)-1,4-dithiane, 1,1,3,3-tetrakis(mercaptomethylthio)propane, 4,6-bis(mercaptomethylthio)-1,3-dithiane, and 2-(2,2-bis(mercaptomethylthio)ethyl)-1,3-dithietane.

9. A process for producing a molded product, comprising:
a step of obtaining the composition for an optical material according to claim 7 by mixing the organic dyes with the polythiourethane or the resin monomer; and
a step of curing the composition for an optical material.

10. The process for producing a molded product according to claim 9 ,
wherein the resin monomer is a polyisocyanate compound and a polythiol compound.

11. The process for producing a molded product according to claim 9 ,
wherein the resin monomer is the polyisocyanate compound and the polythiol compound,
wherein the polyisocyanate compound is at least one kind selected from 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, m-xylylene diisocyanate, dicyclohexylmethane diisocyanate, 1,3-bis(isocyanatomethyl)cyclohexane, 1,4-bis(isocyanatomethyl)cyclohexane, isophorone diisocyanate, 1,6-hexamethylene diisocyanate, and 1,5-pentamethylene diisocyanate, and
wherein the polythiol compound is at least one kind selected from 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-dimercapto

Assignees

• Mitsui Chemicals Inc
• Yamamoto Chemicals Inc

Inventors

• Kojima Kouya
• Hashimoto Toshiya
• Kakinuma Naoyuki
• Kinoshita Satoshi
• Sasaki Hiroyuki

Classifications

• C08K5/0041

  Optical brightening agents, organic pigments · CPC title

• G02B1/041 Primary

  Lenses · CPC title

• G02C7/104

  having spectral characteristics for purposes other than sun-protection · CPC title

• C08K5/0091

  Complexes with metal-heteroatom-bonds · CPC title

• G02C7/108

  Colouring materials · CPC title