Polymerizable composition for optical material and optical material

Patent metadata

Field	Value
Publication number	US-2016237198-A1
Application number	US-201415028751-A
Country	US
Kind code	A1
Filing date	Oct 20, 2014
Priority date	Oct 21, 2013
Publication date	Aug 18, 2016
Grant date	—

Abstract

Disclosed is a polymerizable composition for an optical material containing polyisocyanate (a) which is obtained from a plant-derived raw material and includes a modified product of aliphatic polyisocyanate, alicyclic polyisocyanate (b), and polyol (c) which has a hydroxyl value of 300 mgKOH/g to 650 mgKOH/g and the average number of functional groups of 2 or more and less than 7, and which is obtained from a plant-derived raw material.

First claim

1 . A polymerizable composition for an optical material, comprising:
polyisocyanate (a) which is obtained from a plant-derived raw material and includes a modified product of aliphatic polyisocyanate; alicyclic polyisocyanate (b); and polyol (c) which has a hydroxyl value of 300 mgKOH/g to 650 mgKOH/g and the average number of functional groups of 2 or more and less than 7, and which is obtained from a plant-derived raw material.

2 . A polymerizable composition for an optical material, comprising:
polyisocyanate (a) which is obtained from a plant-derived raw material and includes a modified product of aliphatic polyisocyanate; alicyclic polyisocyanate (b); (poly)glycerin fatty acid esters (e) represented by General Formula (1); and polyol (d) which is a plant-derived compound;

wherein in General Formula (1), R represents a C5 to C19 alkyl group or a C5 to C19 alkenyl group, the alkyl group or the alkenyl group may have a straight chain or a branched chain; X represents a hydrogen atom or a RCO group, wherein R represents a C5 to C19 alkyl group or a C5 to C19 alkenyl group), a plurality of Xs may be identical to each other or different from each other; and n represents an integer of 0 to 3.

3 . The polymerizable composition for an optical material according to claim 1 ,
wherein the modified product is an isocyanurate of aliphatic polyisocyanate, and an isocyanurate monokaryon is contained in the amount of 10 weight % or more in the polyisocyanate (a).

4 . The polymerizable composition for an optical material according to claim 1 ,
wherein a molar ratio ((b)/(a)+(b)) of an isocyanate group of the alicyclic polyisocyanate (b) with respect to the total number of isocyanate groups of the polyisocyanate (a) and the alicyclic polyisocyanate (b) is 0.5 or more and less than 0.8.

5 . The polymerizable composition for an optical material according to claim 1 , further comprising:
polyol (d) which is a plant-derived compound, wherein a molar ratio ((b)/(a)+(b)) of an isocyanate group of the alicyclic polyisocyanate (b) with respect to the total number of isocyanate groups of the polyisocyanate (a) and the alicyclic polyisocyanate (b) is 0.8 to 0.95.

6 . The polymerizable composition for an optical material according to claim 5 , wherein a molar ratio ((d)/(c)+(d)) of a hydroxyl group of the polyol (d) with respect to the total number of hydroxyl groups of the polyol (c) and the polyol (d) is 0.5 to 0.9.

7 . The polymerizable composition for an optical material according to claim 2 , wherein a molar ratio ((d)/(e)+(d)) of a hydroxyl group of the polyol (d) with respect to the total number of hydroxyl groups of the (poly)glycerin fatty acid esters (e) and the polyol (d) is 0.5 to 0.9.

8 . The polymerizable composition for an optical material according to claim 2 , further comprising:
polyol (c) which has a hydroxyl value of 300 mgKOH/g to 650 mgKOH/g and the average number of functional groups of 2 or more and less than 7, and which is obtained from a plant-derived raw material.

9 . The polymerizable composition for an optical material according to claim 8 ,
wherein a molar ratio ((b)/(a)+(b)) of an isocyanate group of the alicyclic polyisocyanate (b) with respect to the total number of isocyanate groups of the polyisocyanate (a) and the alicyclic polyisocyanate (b) is 0.2 to 0.85.

10 . The polymerizable composition for an optical material according to claim 1 ,
wherein the polyol (c) is obtained by using at least one selected from glycerin, sorbitol, isosorbide, sucrose, 1,4-butanediol, 1,3-butanediol, and 1,3-propanediol which are plant-derived raw materials as a raw material.

11 . The polymerizable composition for an optical material according to claim 10 ,
wherein the polyol (c) is at least one selected from polyether polyol, polyester polyol, polycarbonate polyol, and polyacryl polyol.

12 . The polymerizable composition for an optical material according to claim 2 ,
wherein the polyol (d) is at least one selected from glycerin, sorbitol, isosorbide, sucrose, 1,3-butanediol, 1,4-butanediol, and 1,3-propanediol.

13 . The polymerizable composition for an optical material according to claim 1 , further comprising:
a non-metal catalyst.

14 . A polyurethane molded product which is obtained by polymerizing and curing the polymerizable composition for an optical material according to claim 1 .

15 . The polyurethane molded product according to claim 14 ,
wherein a degree of biomass is 20% or more and less than 50%.

16 . A polyurethane molded product which is obtained by polymerizing and curing the polymerizable composition for an optical material according to claim 2 .

17 . The polyurethane molded product according to claim 16 ,
wherein a degree of biomass is 20% to 75%.

18 . The polyurethane molded product according to claim 14 , wherein Tg is 60° C. or higher.

19 . An optical material which is comprised of the polyurethane molded product according to claim 14 .

20 . A plastic spectacle lens which is comprised of the optical material according to claim 19 .

21 . A plastic polarization lens in which a layer obtained by polymerizing and curing the polymerizable composition for an optical material according to claim 1 is laminated over at least one surface of a polarizing film.

22 . A process for producing a plastic spectacle lens, comprising:
a step of injecting the polymerizable composition for an optical material according to claim 1 into a lens casting mold; and a step of polymerizing and curing the polymerizable composition for an optical material.

23 . A process for producing a plastic polarization lens, comprising:
a step of fixing a polarizing film into a lens casting mold in a state in which at least one surface of the polarizing film is separated from a mold; a step of injecting the polymerizable composition for an optical material according to claim 1 into a gap between the polarizing film and the mold; and
a step of laminating a layer comprised of a polyurethane resin over at least one surface of the polarizing film by polymerizing and curing the polymerizable composition for an optical material.

24 . The polymerizable composition for an optical material according to claim 2 ,
wherein the modified product is an isocyanurate of aliphatic polyisocyanate, and an isocyanurate monokaryon is contained in the amount of 10 weight % or more in the polyisocyanate (a).

25 . The polymerizable composition for an optical material according to claim 7 , further comprising:
polyol (c) which has a hydroxyl value of 300 mgKOH/g to 650 mgKOH/g and the average number of functional groups of 2 or more and less than 7, and which is obtained from a plant-derived raw material.

26 . The polymerizable composition for an optical material according to claim 8 ,
wherein the polyol (c) is obtained by using at least one selected from glycerin, sorbitol, isosorbide, sucrose, 1,4-butanediol, 1,3-butanediol, and 1,3-propanediol which are plant-derived raw materials as a raw material.

27 . The polymerizable composition for an optical material according to claim 5 ,
wherein the polyol (d) is at least one selected from glycerin, sorbitol, isosorbide, sucrose, 1,3-butanediol, 1,4-butanediol, and 1,3-propanediol.

Assignees

• Mitsui Chemicals Inc

Inventors

• Tsukada Hidetaka
• Goto Kenichi
• Miyata Atsushi
• Nakagawa Toshihiko
• Yamasaki Satoshi
• Morita Hirokazu

Classifications

• C08G18/161

  containing two or more components to be covered by at least two of the groups C08G18/166, C08G18/18 or C08G18/22 · CPC title

• B32B2307/42

  Polarizing, birefringent, filtering · CPC title

• B32B27/36

  comprising polyesters · CPC title

• C08G18/4009

  Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64 · CPC title

• G02B5/3033

  in the form of a thin sheet or foil, e.g. Polaroid · CPC title