IP Library Granted Patent US 10,934,451
Granted Patent B2
US 10,934,451 · App. 14/411,248 · Granted Mar 2, 2021

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

Inventors: Mathieu Feuillade (Kawasaki, JP); Guillaume Cantagrel (Kawasaki, JP)
Assignees: Nikon Corporation; Essilor International
C09D143/02C08F30/02C08F130/02C08F230/02C08G75/045C08G75/12C08K3/22C08K9/04C08K2003/2241C08K2003/2244Y10T428/31935
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Quick Facts
Patent No.
US 10,934,451
App. No.
14/411,248
Granted
Mar 2, 2021
Kind
B2
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.

Claims (23)

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.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 6, 2018
From: ESSILOR INTERNATIONAL (COMPAGNIE GÉNÉRALE D'OPTIQUE)
To: ESSILOR INTERNATIONAL
Reel/Frame 045853/0275 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 29, 2015
From: NIKON AND ESSILOR INTERNATIONAL JOINT RESEARCH CENTER CO., LTD
To: NIKON CORPORATION; ESSILOR INTERNATIONAL (COMPAGNIE GENERALE D'OPTIQUE)
Reel/Frame 034843/0878 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 13, 2015
From: FEUILLADE, MATHIEU; CANTAGREL, GUILLAUME
To: NIKON AND ESSILOR INTERNATIONAL JOINT RESEARCH CENTER CO., LTD
Reel/Frame 034692/0618 →