Bleaching agent, preparation and use of the same with polymerizable compositions for optical materials

Patent metadata

Field	Value
Publication number	US-12534548-B2
Application number	US-202017774680-A
Country	US
Kind code	B2
Filing date	Nov 11, 2020
Priority date	Nov 12, 2019
Publication date	Jan 27, 2026
Grant date	Jan 27, 2026

Abstract

The present invention relates to a bleaching agent comprising: (A) a polymerizable component comprising an aromatic ester compound including two or more allyloxycarbonyl groups, (B) a colouring component comprising particles of a blue pigment (b1), (C) a polymeric dispersing agent to disperse the particles of the colouring component (B) in the polymerizable component (A), the particles of the colouring component (B) having an average size equal to or lower than 400 nm. The present invention also relates to the preparation and use of the above bleaching agent with polymerizable compositions for optical materials.

First claim

The invention claimed is:

1 . A bleaching agent comprising:
(A) a polymerizable component, (B) a colouring component comprising particles of a blue pigment (b1), (C) a polymeric dispersing agent to disperse the particles of the colouring component (B) in the polymerizable component (A),
wherein the particles of the colouring component (B) have a z-average size equal to or lower than 400 nm, as measured by Dynamic Light Scattering technique according to the method ISO 22412:2017,
wherein the polymeric dispersing agent (C) comprises a polymeric part and one or more pigment affinitive-groups selected from: carboxylic group, sulphate group, sulphonate group, amine salts, phosphate group, phosphonate group, carbamate group, urea group, amide group or amine group, and
wherein said polymerizable component (A) is a mixture of compounds selected from the group consisting of the following Formulas (3), (4) and (5);

wherein in the Formula (4), X represents a divalent group derived from a linear or branched aliphatic diol having 2 to 8 carbon atoms or a trivalent to hexavalent group derived from a linear or branched aliphatic polyol having 3 to 10 carbon atoms and having 3 to 6 hydroxyl groups, and n is an integer of 2 to 6;

wherein in the Formula (5), X represents a divalent group derived from a linear or branched aliphatic diol having 2 to 8 carbon atoms or a trivalent to hexavalent group derived from a linear or branched aliphatic polyol having 3 to 10 carbon atoms and having 3 to 6 hydroxyl groups, m and n represent integers of 0 to 6, and the sum of m and n is an integer of 2 to 6; with the proviso that when no compounds of Formula (3) and (4) are present, in the Formula (5) n represents integers of 1 to 6 and the sum of m and n is an integer of 2 to 6.

2 . Bleaching agent according to claim 1 , wherein said colouring component (B) is contained in the range of 0.1% to 5.0% by weight with respect to said component (A).

3 . Bleaching agent according to claim 1 , wherein said polymeric dispersing agent (C) is contained in the range of 0.1% to 10% by weight with respect to said component (A).

4 . Bleaching agent according to claim 1 , wherein said polymerizable component (A) is a compound having the following Formula 1:

wherein in the Formula (1):
n is an integer of 2 to 6,
R 1 indicates a hydrogen atom or a methyl group, a plurality of present R 1 's may be the same or different,
X is a divalent to hexavalent organic group derived from an aromatic compound having 6 to 12 carbon atoms.

5 . Bleaching agent according to claim 1 , wherein the colouring component (B) includes particles of one or more further pigments (b2), different from the blue pigment (b1).

6 . Bleaching agent according to claim 5 , wherein the weight ratio between the particles of the pigment (b1) and the particles of the pigment (b2) is within the range of from 5:1 to 15:1.

7 . Bleaching agent according to claim 1 , wherein the particles of the colouring component (B) have a z-average size equal to or lower than 280 nm, as measured by Dynamic Light Scattering technique according to the method ISO 22412:2017.

8 . Bleaching agent according to claim 1 , wherein the particles of the colouring component (B) have a z-average size equal to or higher than 20 nm as measured by Dynamic Light Scattering technique according to the method ISO 22412:2017.

9 . A Process for preparing a bleaching agent according to claim 1 comprising the following steps in sequence:
providing a pre-mixture by mixing:
(A) a polymerizable component,
(B) a colouring component comprising particles of a blue pigment (b1),
(C) a polymeric dispersing agent to disperse the particles of the colouring component (B) in the polymerizable component (A),
homogenizing the pre-mixture to obtain a bleaching agent in which the particles of the colouring component (B) have a z-average size equal to or lower than 400 nm, as measured by Dynamic Light Scattering technique according to the method ISO 22412:2017,
wherein the polymeric dispersing agent (C) comprises a polymeric part and one or more pigment affinitive-groups selected from: carboxylic group, sulphate group, sulphonate group, amine salts, phosphate group, phosphonate group, carbamate group, urea group, amide group or amine group, and
wherein said polymerizable component (A) is a mixture of compounds selected from the group consisting of the following Formulas (3), (4) and (5);

wherein in the Formula (4), X represents a divalent group derived from a linear or branched aliphatic diol having 2 to 8 carbon atoms or a trivalent to hexavalent group derived from a linear or branched aliphatic polyol having 3 to 10 carbon atoms and having 3 to 6 hydroxyl groups, and n is an integer of 2 to 6;

wherein in the Formula (5), X represents a divalent group derived from a linear or branched aliphatic diol having 2 to 8 carbon atoms or a trivalent to hexavalent group derived from a linear or branched aliphatic polyol having 3 to 10 carbon atoms and having 3 to 6 hydroxyl groups, m and n represent integers of 0 to 6, and the sum of m and n is an integer of 2 to 6; with the proviso that when no compounds of Formula (3) and (4) are present, in the Formula (5) n represents integers of 1 to 6 and the sum of m and n is an integer of 2 to 6.

10 . Process according to claim 9 , wherein, in the step of providing a pre-mixture, said colouring component (B) is mixed in the range of 0.1% to 5.0% by weight with respect to said component (A).

11 . Process according to claim 9 , wherein, in the step of providing a pre-mixture, said polymeric dispersing agent (C) is mixed in the range of 0.1% to 10% by weight with respect to said component (A).

12 . Process according to claim 9 , wherein the step of homogenizing the pre-mixture is carried out by sonication by means of a sonotrode.

13 . Process according to claim 9 , wherein the step of homogenizing the pre-mixture is a high-pressure homogenization (HPH) step.

14 . A polymerizable composition for an optical material comprising:
(A) a polymerizable component, (B) a colouring component comprising particles of a blue pigment (b1); (C) a polymeric dispersing agent to disperse the particles of the colouring component (B) in the polymerizable component (A); (D) an ultraviolet absorbing agent; and (E) a radical polymerization initiator,
wherein the particles of the colouring component (B) have a z-average size equal to or lower than 400 nm, as measured by Dynamic Light Scattering technique according to the method ISO 22412:2017,
the polymeric dispersing agent (C) comprises a polymeric part and one or more pigment affinitive-groups selected from: carboxylic group, sulphate group, sulphonate group, amine salts, phosphate group, phosphonate group, carbamate group, urea group, amide group or amine group, and
wherein said polymerizable component (A) is a mixture of compounds selected from the group consisting of the following Formulas (3), (4) and (5):

Assignees

• Mitsui Chemicals Inc

Inventors

• Vecchione Andrea
• Forestieri Roberto
• Mariani Francesco
• Bos Willem

Classifications

• C08F18/18 Primary

  Diallyl phthalate · CPC title

• C08F2/48

  by ultraviolet or visible light · CPC title

• C08F18/16 Primary

  with alcohols containing three or more carbon atoms · CPC title

• G02B1/04

  made of organic materials, e.g. plastics (G02B1/08 takes precedence) · CPC title

• C08F2/44

  Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers · CPC title