IP Library Granted Patent US 9,103,969
Granted Patent B2
US 9,103,969 · App. 12/922,136 · Granted Aug 11, 2015

Curable coating composition modified with a cleavable surfactant for improving adhesion in multilayered coating stacks

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Quick Facts
Patent No.
US 9,103,969
App. No.
12/922,136
Granted
Aug 11, 2015
Kind
B2
Abstract

The present invention is dedicated to a process for improving the adhesion properties between a first coating obtained from a curable composition and a second coating, through the incorporation of a cleavable surfactant in said curable composition and subsequent cleavage thereof. Said process comprises: depositing onto the substrate of an optical article a first layer of a first curable composition comprising at least one cleavable surfactant, curing at least partially said first curable composition, thereby forming a first coating, forming a second coating onto said first coating, wherein, after said first curable composition has been deposited onto the substrate, and before deposition of the second coating, said optical article is subjected to a treatment step resulting in a cleavage of at least a portion of the cleavable surfactant. Curable compositions containing cleavable surfactants and optical articles having deposited thereon stacks of coatings formed by the above process are also described.

Claims (23)

1. A process for preparing an optical article, comprising:

(a) providing an optical article comprising a substrate having an exposed surface,

(b) depositing onto said exposed surface of the substrate a first layer of a first curable composition comprising at least one cleavable surfactant, wherein the cleavable surfactant is selected from the group consisting of:

(i) a compound of formula IX or X:

in which the polar head is a polar group, the hydrophobic tail is a hydrophobic group, R1, R2 and R3 independently represent H, aryl, alkyl, halogen, a hydrophobic tail or a polar head or any group compatible with the conditions of a Diels-Alder cycloaddition reaction;

(ii) a compound of formula XI:

in which R5, R6, R7 and R8 independently represent H, aryl, alkyl, halogen, or any group compatible with the conditions of a Diels-Alder cycloaddition reaction, with the proviso that at least one of R5, R6, R7 and R8 is an alkyl group of formula CmH2m+1, wherein m is an integer ranging from 6 to 24, the R4 groups independently represent hydrophilic groups, and n is an integer ranging from 1 to 5; and

(iii) sodium dodecyl sulfate, sodium dodecyl benzene sulfonate, or a mixture of both;

(c) curing at least partially said first curable composition, thereby forming a first coating,

(d) forming a second coating onto said first coating, and

(e) obtaining an optical article comprising a substrate successively coated with said first coating and said second coating, said first coating adhering to said second coating,

wherein, after said first curable composition has been deposited onto the exposed surface of the substrate, and before step (d), said optical article is subjected to a treatment step resulting in a cleavage of at least a portion of the cleavable surfactant, and

wherein no surface treatment with energetic species selected from ions, radicals, photons or electrons is performed on the first coating before proceeding to step (d).

2. The process of claim 1 , wherein said first coating is a sol-gel coating or a (meth)acrylate based coating.

3. The process of claim 1 , wherein the first curable composition further comprises at least one compound of formula:

R n Si(X) 4-n   (I)

or a hydrolyzate thereof, in which the R groups are identical or different and represent monovalent organic groups linked to the silicon atom through a carbon atom, the X groups are identical or different and represent hydrolyzable groups, and n is an integer equal to 1 or 2.

4. The process of claim 3 , wherein the first curable composition does not comprise any surfactant that is not capable of being cleaved by said treatment step.

5. The process of claim 1 , wherein the first curable composition further comprises at least one compound of formula:

R n′ Y m Si(X) 4-n′-m   (II)

or hydrolyzates thereof, in which the R groups are identical or different and represent monovalent organic groups linked to the silicon atom through a carbon atom, the Y groups are identical or different and represent monovalent organic groups linked to the silicon atom through a carbon atom and containing at least one epoxy function, the X groups are identical or different and represent hydrolysable groups, m and n′ are integers such that m is equal to 1 or 2 and n′+m=1 or 2.

6. The process of claim 1 , wherein the thickness of the first coating ranges from 1 to 15 μm.

7. The process of claim 1 , wherein the thickness of the first coating ranges from 5 to 250 nm.

Assignments (2)
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 Jun 7, 2012
From: BITEAU, JOHN
To: ESSILOR INTERNATIONAL (COMPAGNIE GENERALE D'OPTIQUE)
Reel/Frame 028337/0008 →