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

Patent metadata

Field	Value
Publication number	US-10934451-B2
Application number	US-201314411248-A
Country	US
Kind code	B2
Filing date	Jun 26, 2013
Priority date	Jun 26, 2012
Publication date	Mar 2, 2021
Grant date	Mar 2, 2021

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. A liquid polymerizable composition suitable for preparing a transparent optical article, said composition comprising:
a liquid monomer composition comprising:
a 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 or S,
n=0,
m and p, identical or different, represent an integer from 0 to 4,
Q represents a polymerizable function selected from the group consisting of acrylate, methacrylate, and thiol, and
the other(s) among R 1 a, R 2 a and R 3 a, identical or different, represent(s) an hydrogen atom, a phenyl, an C1-C6 alkoxy, C1-C6 alkylthio, aryloxy, arylthio, aryl C1-C6 alkoxy, or aryl C1-C6 alkylthio, or

a mixture of two different monomers M1 and M2 which are 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=X and M1 and M2 further contain functions which are able to react together to form a polymer, and
ZrO 2 nanoparticles homogeneously dispersed in said monomer of formula (I) 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 liquid polymerizable composition is transparent after polymerization so that it is suitable for preparing a transparent optical article,
wherein the amount of said ZrO 2 nanoparticles in the polymerizable composition is comprised between 5 and 50% w/w, based on the total weight of the liquid polymerizable composition,
wherein the particle size of the ZrO 2 nanoparticles is less than 50 nm, and
wherein said liquid polymerizable composition after polymerization has a refractive index higher than 1.511 at 594 nm.

2. The liquid polymerizable composition of claim 1 , wherein said phosphine oxide of formula (Ia) is selected from the group consisting of:

3. The liquid polymerizable composition of claim 1 , wherein the amount of said ZrO 2 nanoparticles in the polymerizable composition is comprised between 10 and 40% w/w, based on the total weight of the liquid polymerizable composition.

4. The liquid polymerizable composition of claim 1 , wherein the amount of said ZrO 2 nanoparticles in the polymerizable composition is comprised between 30 and 35% w/w, based on the total weight of the liquid polymerizable composition.

5. The liquid polymerizable composition of claim 1 , wherein said ZrO 2 nanoparticles have a particle size between 30 nm and 5 nm.

6. The liquid polymerizable composition of claim 1 , further comprising a mold release agent, a photostabilizer, an antioxidant, a dye-anti-coloring agent, a filler, a UV light absorber or an optical brightener.

Assignees

• Nikon Corp
• Essilor Int

Inventors

• Feuillade Mathieu
• Cantagrel Guillaume

Classifications

• C08G75/045 Primary

  from mercapto compounds and unsaturated compounds · CPC title

• C08K2201/011

  Nanostructured additives · CPC title

• C08F30/02

  containing phosphorus · CPC title

• C09D143/02 Primary

  Homopolymers or copolymers of monomers containing phosphorus · CPC title

• C08F130/02 Primary

  containing phosphorus · CPC title