Liquid polymerizable composition comprising an anhydride derivative monomer and mineral nanoparticles dispersed therein, and its use to manufacture an optical article

Patent metadata

Field	Value
Publication number	US-10428221-B2
Application number	US-201315105266-A
Country	US
Kind code	B2
Filing date	Dec 20, 2013
Priority date	Dec 20, 2013
Publication date	Oct 1, 2019
Grant date	Oct 1, 2019

Abstract

A liquid polymerizable composition including an anhydride derivative monomer with mineral nanoparticles homogeneously dispersed therein, as well as its use for the preparation of a transparent polymeric material having a high refractive index and its use in the optical field.

First claim

The invention claimed is:

1. A liquid polymerizable composition comprising:
a liquid monomer composition containing a monomer of formula (I):

wherein:
R and R′, identical or different, represent a hydrogen atom or a methyl group,
X is —O—, —S—, —NR1- or —CR2R3-,
R1 is selected from the group consisting of aryl, heteroaryl, aryl C1-C6 alkyl and heteroaryl C1-C6 alkyl, R2 and R3, identical or different, are selected from the group consisting of aryl, heteroaryl, aryl C1-C6 alkyl, heteroaryl C1-C6 alkyl, aryloxy, arylthio, aryl C1-C10 alkyloxy, heteroaryl C1-C10 alkyloxy, aryl C1-C10 alkylthio, and heteroaryl C1-C10 alkylthio, and
mineral nanoparticles homogeneously dispersed in said monomer composition, wherein said mineral nanoparticles consist of a material selected from the group consisting of ZnS, ZrO 2 , TiO 2 and BaTiO 3 .

2. The liquid polymerizable composition of claim 1 , wherein in formula (I), R and R′ are identical.

3. The liquid polymerizable composition of claim 1 , wherein in formula (I), X is —O—, —NR1- or —CR2R3-.

4. The liquid polymerizable composition of claim 1 , wherein in formula (I), X is —O—.

5. The liquid polymerizable composition of claim 1 , wherein in formula (I), X is —NR1- and R1 is selected from the group consisting of aryl, heteroaryl, aryl C1-C6 alkyl and heteroaryl C1-C6 alkyl.

6. The liquid polymerizable composition of claim 1 , wherein in formula (I), X is —CR2R3- and R2 and R3, identical or different, are selected from the group consisting of aryl, heteroaryl, aryl C1-C6 alkyl, heteroaryl C1-C6 alkyl, aryloxy, arylthio, aryl C1-C10 alkyloxy, heteroaryl C1-C10 alkyloxy, aryl C1-C10 alkylthio, and heteroaryl C1-C10 alkylthio.

7. The liquid polymerizable composition of claim 1 , wherein said nanoparticles have a particle size less than 50 nm.

8. The liquid polymerizable composition of claim 1 , wherein the amount of said mineral nanoparticles in the polymerizable composition is comprised between 5% w/w and 60% w/w, based on the total weight of the liquid polymerizable composition.

9. An optical substrate coated with the liquid composition according to claim 1 .

10. The optical substrate according to claim 9 , wherein the article is an ophthalmic lens or an optical lens for optical instrument.

11. An optical article cured of the liquid composition according to claim 1 .

12. An optical article comprising:
(a) an optical substrate, and
(b) a coating obtained by thermal and/or UV curing of the liquid polymerizable composition according to claim 1 .

13. The optical article according to claim 12 , wherein the article is an ophthalmic lens or an optical lens for optical instrument.

14. The liquid polymerizable composition of claim 1 , wherein the monomer of formula (I) is methacrylic anhydride.

15. The liquid polymerizable composition of claim 1 , wherein said nanoparticles have a particle size between 30 nm and 5 nm.

16. The liquid polymerizable composition of claim 1 , wherein the amount of said mineral nanoparticles in the polymerizable composition is comprised between 10% w/w and 50% w/w, based on the total weight of the liquid polymerizable composition.

17. A process for increasing the refractive index of a polymeric material obtained by thermal and/or UV curing of a liquid monomer composition containing a monomer of formula (I):

wherein:
R and R′, identical or different, represent a hydrogen atom or a methyl group,
X is —O—, —S—, —NR1- or —CR2R3-,

R1 is selected from the group consisting of aryl, heteroaryl, aryl C1-C6 alkyl and heteroaryl C1-C6 alkyl, R2 and R3, identical or different, are selected from the group consisting of aryl, heteroaryl, aryl C1-C6 alkyl, heteroaryl C1-C6 alkyl, aryloxy, arylthio, aryl C1-C10 alkyloxy, heteroaryl C1-C10 alkyloxy, aryl C1-C10 alkylthio, and heteroaryl C1-C10 alkylthio, and
said process comprising the step of homogeneously dispersing mineral nanoparticles in said monomer composition, wherein said mineral nanoparticles consist of a material selected from the group consisting of ZnS, ZrO 2 , TiO 2 and BaTiO 3 .

Assignees

• Essilor Int
• Nikon Corp

Inventors

• Cantagrel Guillaume

Classifications

• G02B2207/101

  Nanooptics · CPC title

• C09D7/62

  modified by treatment with other compounds · CPC title

• C08K2003/2244

  of zirconium · CPC title

• G02B1/041

  Lenses · CPC title

• G02B1/043

  Contact lenses · CPC title