Liquid polymerizable composition comprising mineral nanoparticles and its use to manufacture an optical article

Patent metadata

Field	Value
Publication number	US-12173176-B2
Application number	US-202017247869-A
Country	US
Kind code	B2
Filing date	Dec 28, 2020
Priority date	Jun 26, 2012
Publication date	Dec 24, 2024
Grant date	Dec 24, 2024

Abstract

Disclosed is a liquid polymerizable composition including a phosphine oxide or a phosphine sulphide monomer composition 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. An ophthalmic lens or an optical lens for an optical instrument, comprising an optical substrate coated with a cured product of a liquid polymerizable composition comprising:
a liquid monomer composition as a continuous phase containing:
phosphine oxide of formula (Ia):

wherein:
at least one among R 1 a, R 2 a and R 3 a, identical or different, represents:
—(R4) n —X—(R5-Y) m —(R6) p -Q wherein:
R4, R5 and R6, identical or different, represent a C1-C6 alkylene group, one or several carbon atoms of which may be replaced with a phenylene group,
X and Y, identical or different, represent O, S, or —NR—, wherein R is a C1-C6 alkyl group,
n, m and p, identical or different, represent an integer from 0 to 4,
Q represents a polymerizable function, preferably chosen from acrylate, methacrylate, thioacrylate, thiomethacrylate, or thiol,
and the other(s) among R 1 a, R 2 a and R 3 a, identical or different, represent(s) a hydrogen atom, phenyl, C1-C6alkoxy, C1-C6alkylthio, aryloxy, arylthio, aryl C1-C6alkoxy, or aryl C1-C6alkylthio,
or a mixture of two different monomers M1 and M2 as a continuous phase, said monomers M1 and M2 being able to react together and form the phosphine oxide of formula (Ia), wherein M1 or M2 or both M1 and M2 contain the function P=O and M1 and M2 further contain functions which are able to react together to form a polymer,

and mineral nanoparticles homogeneously dispersed in said phosphine oxide of formula (Ia), or in said mixture of two different monomers M1 and M2 which are able to react together and form the phosphine oxide of formula (Ia),
wherein said mineral nanoparticles are selected from the group consisting of ZnS, ZrO 2 , TiO 2 and BaTiO 3 ,
wherein the phosphine oxide of formula (Ia) is from 50% to 95% by weight of the liquid polymerizable composition.

2. The ophthalmic lens or optical lens for an optical instrument of claim 1 , wherein R1, R2 and R3 bearing no polymerizable function, identical or different, represent(s) a phenyl, aryloxy, arylthio, arylC1-C10alkyloxy, or aryl C1-C10alkylthio.

3. The ophthalmic lens or optical lens for an optical instrument of claim 1 , wherein said phosphine oxide of formula (Ia) is selected from the group consisting of:

4. The ophthalmic lens or optical lens for an optical instrument of claim 1 , wherein said nanoparticles have a particle size less than 50 nm.

5. The ophthalmic lens or optical lens for an optical instrument of claim 1 , wherein said nanoparticles are ZnS nanoparticles coated with one or more thiol-containing compounds.

6. The ophthalmic lens or optical lens for an optical instrument of claim 5 , wherein said ZnS nanoparticles are coated with mercaptoethanol, thiophenol, mercaptophenol, or a mixture thereof.

7. The ophthalmic lens or optical lens for an optical instrument of claim 5 , wherein said nanoparticles of ZnS are coated with a mixture of mercaptoethanol and thiophenol, wherein a process for forming the coated ZnS nanoparticles comprises mixing a zinc source, mercaptoethanol and thiophenol with a molar ratio of mercaptoethanol and thiophenol over Zn of a zinc source comprised between 2.0 and 0.1.

8. The ophthalmic lens or optical lens for an optical instrument of claim 5 , wherein said nanoparticles of ZnS are coated with mercaptoethanol, wherein a process for forming the coated ZnS nanoparticles comprises mixing a zinc source and mercaptoethanol with a molar ratio of mercaptoethanol over Zn of a zinc source comprised between 1.3 and 1.6.

9. The ophthalmic lens or optical lens for an optical instrument of claim 5 , wherein said nanoparticles of ZnS have crystal size comprised between 3 and 10 nm, and the particle size of the nanoparticles of ZnS coated with said thiol-containing compound(s) is comprised between 4 and 80 nm.

10. The ophthalmic lens or optical lens for an optical instrument of claim 1 , wherein the amount of said mineral nanoparticles in the liquid polymerizable composition is comprised between 5 and 50% w/w based on the total weight of the liquid polymerizable composition.

11. The ophthalmic lens or optical lens for an optical instrument according to claim 1 , wherein the optical substrate is a thermoplastic resin or a thermoset or photocured resin.

Assignees

• Nikon Corp
• Essilor Int

Inventors

• Feuillade Mathieu
• Cantagrel Guillaume

Classifications

• C08K2003/2244

  of zirconium · CPC title

• C08K2003/2241

  Titanium dioxide · CPC title

• C08K9/04

  Ingredients treated with organic substances {(treated with macromolecular compounds C08K9/08)} · CPC title

• C08K3/22

  of metals · CPC title

• C08F30/02

  containing phosphorus · CPC title