IP Library Patent Application 15106357
Patent Application
App. No. 15/106,357

LIQUID POLYMERIZABLE COMPOSITION COMPRISING AN AMIDE OR A THIOAMIDE DERIVATIVE MONOMER AND MINERAL NANOPARTICLES DISPERSED THEREIN, AND ITS USE TO MANUFACTURE AN OPTICAL ARTICLE

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Patent No.
US None
App. No.
15/106,357
Abstract

A liquid polymerizable composition including an amide or a thioamide 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.

Claims (67)

1 - 23 . (canceled)

24 . A liquid polymerizable composition comprising:

a liquid monomer composition containing a monomer of formula (I):

wherein:

R represents a hydrogen atom or a methyl group,

A represents a hydrocarbon chain comprising 1, 2, 3 or 4 carbon atoms,

Y is an oxygen atom or a sulphur atom

X is —O—, —S— or —NR2-,

R1 and R2, identical or different, are a hydrogen atom or a C1-C6 alkyl, and

B represents a C1-C6 alkyl, aryl, heteroaryl, aryl C1-C6alkyl or heteroaryl C1-C6alkyl,

or B is absent and R1 and X form a 5-membered heterocycle, such as a 2-imidazolidinone, optionally substituted on —NH—, 2-oxazolidinone or 2-thiazolidinone,

or B represents:

wherein:

R′ represents a hydrogen atom or a methyl group,

A′ represents a hydrocarbon chain comprising 1, 2, 3 or 4 carbon atoms,

Y′ is an oxygen atom or a sulphur atom,

X′ is —O—, —S— or —NR2′-,

R1′ and R2′, identical or different, are a hydrogen atom or a C1-C6 alkyl, and

Q represents a hydrocarbon chain comprising 1, 2, 3 or 4 carbon atoms substituted with an aryl, heteroaryl, aryl C1-C6alkyl, aryloxy, arylthio, aryl C1-C10alkyloxy, aryl C1-C10alkylthio, heteroaryl C1-C6alkyl, heteroaryl C1-C10alkyloxy, or heteroaryl C1-C10alkylthio, and

mineral nanoparticles homogeneously dispersed in said monomer composition.

25 . The liquid polymerizable composition of claim 24 , wherein said mineral nanoparticles are chosen among ZnS, ZrO 2 , TiO 2 or BaTiO 3 .

26 . The liquid polymerizable composition of claim 24 , wherein in formula (I), Y is an oxygen atom.

27 . The liquid polymerizable composition of claim 24 , wherein in formula (I), Y is a sulphur atom.

28 . The liquid polymerizable composition of claim 24 , wherein in formula (I), B is absent and R1 and X form a 2-imidazolidinone, optionally substituted on —NH—, 2-oxazolidinone or 2-thiazolidinone.

29 . The liquid polymerizable composition of claim 28 , wherein the monomer of formula (I) is the following one:

30 . The liquid polymerizable composition of claim 24 , wherein in formula (I), Y is an oxygen atom and X is —NH— or Y is an oxygen atom and X is —O—.

31 . The liquid polymerizable composition of claim 30 , wherein the monomer of formula (I) is one of the following ones:

32 . The liquid polymerizable composition of claim 24 , wherein in formula (I), B represents:

wherein:

R′ represents a hydrogen atom or a methyl group, in particular a hydrogen atom,

A′ represents a hydrocarbon chain comprising 1, 2, 3 or 4 carbon atoms, in particular is —CH2-CH2,

X′ is —O—,

R1′ is a hydrogen atom or a C1-C6 alkyl, in particular a hydrogen atom,

Q represents a hydrocarbon chain comprising 1, 2, 3 or 4 carbon atoms substituted with an aryl, heteroaryl, aryl C1-C6alkyl, aryloxy, arylthio, aryl C1-C10alkyloxy, aryl C1-C10alkylthio, heteroaryl C1-C6alkyl, heteroaryl C1-C10alkyloxy, or heteroaryl C1-C10alkylthio.

33 . The liquid polymerizable composition of claim 32 , wherein the monomer of formula (I) is the following one:

34 . The liquid polymerizable composition of claim 24 , wherein said nanoparticles have a particle size less than 50 nm, preferably between 30 nm and 5 nm.

35 . The liquid polymerizable composition of claim 24 , wherein said nanoparticles are chosen among of ZnS nanoparticles coated with one or more thiol-containing compounds, such as mercaptoethanol, thiophenol, mercaptophenol, or a mixture thereof.

36 . The liquid polymerizable composition of claim 35 , wherein said nanoparticles of ZnS are coated with a mixture of mercaptoethanol and thiophenol, preferably with a molar ratio of mercaptoethanol and thiophenol over Zn comprised between 2.0 and 0.1, preferably between 0.6 and 0.3.

37 . The liquid polymerizable composition of claim 35 , wherein said nanoparticles of ZnS are coated with mercaptoethanol preferably with a molar ratio of mercaptoethanol over ZnS is comprised between 1.3 and 1.6.

38 . The liquid polymerizable composition of claim 35 , wherein said nanoparticles of ZnS have crystal size comprised between 3 nm and 10 nm, and the particle size of the nanoparticles of ZnS coated with said thiol-containing compound(s) is comprised between 4 nm and 80 nm.

39 . The liquid polymerizable composition of claim 24 , wherein the amount of said mineral nanoparticles in the polymerizable composition is comprised between 5% w/w and 60% w/w, preferably between 10% w/w and 50% w/w, based on the total weight of the liquid polymerizable composition.

40 . An optical substrate coated with the liquid composition according to claim 24 .

41 . An optical article cured of the liquid composition according to claim 24 .

42 . 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 24 .

43 . The optical substrate according to claim 40 , wherein the article is an ophthalmic lens or an optical lens for optical instrument.

44 . The optical article according to claim 41 , wherein the article is an ophthalmic lens or an optical lens for optical instrument.

45 . 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 represents a hydrogen atom or a methyl group,

A represents a hydrocarbon chain comprising 1, 2, 3 or 4 carbon atoms,

Y is an oxygen atom or a sulphur atom

X is —O—, —S— or —NR2-,

R1 and R2, identical or different, are a hydrogen atom or a C1-C6 alkyl, and

B represents a C1-C6 alkyl, aryl, heteroaryl, aryl C1-C6alkyl or heteroaryl C1-C6alkyl,

or B is absent and R1 and X form a 5-membered heterocycle, such as a 2-imidazolidinone, optionally substituted on —NH—, 2-oxazolidinone or 2-thiazolidinone

or B represents:

wherein:

R′ represents a hydrogen atom or a methyl group,

A′ represents a hydrocarbon chain comprising 1, 2, 3 or 4 carbon atoms,

Y′ is an oxygen atom or a sulphur atom,

X′ is —O—, —S— or —NR2′-,

R1′ and R2′, identical or different, are a hydrogen atom or a C1-C6 alkyl, and

Q represents a hydrocarbon chain comprising 1, 2, 3 or 4 carbon atoms substituted with aryl, heteroaryl, aryl C1-C6alkyl, aryloxy, arylthio, aryl C1-C10alkyloxy, aryl C1-C10alkylthio, heteroaryl C1-C6alkyl, heteroaryl C1-C10alkyloxy, or heteroaryl C1-C10alkylthio,

said process comprising the step of dispersing said mineral nanoparticles in said monomer composition.

46 . The process according to claim 45 , wherein said mineral nanoparticles are chosen among ZnS, ZrO 2 , TiO 2 or BaTiO 3 .

Assignments (4)
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 Aug 3, 2016
From: ASSIGNEE: NIKON AND ESSILOR INTERNATIONAL JOINT RESEARCH CENTER CO., LTD
To: ESSILOR INTERNATIONAL (COMPAGNIE GENERALE D'OPTIQUE); NIKON CORPORATION
Reel/Frame 039332/0916 →
CORRECTIVE ASSIGNMENT TO CORRECT THE NAME OF THE ASSIGNEE PREVIOUSLY RECORDED ON REEL 039002 FRAME 0443. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT OF ASSIGNORS INTEREST. Recorded Jul 1, 2016
From: CANTAGREL, GUILLAUME
To: NIKON AND ESSILOR INTERNATIONAL JOINT RESEARCH CENTER CO., LTD
Reel/Frame 039230/0001 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 24, 2016
From: CANTAGREL, GUILLAUME
To: NIKON AND ESSILOR INTERNATION JOINT RESEARCH CENTER CO., LTD
Reel/Frame 039002/0443 →