# US 2016/0259093 A1 · Method for improving the edging of an optical article by providing a temporary layer of an organic matter

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- Number: US 2016/0259093 A1
- Document ID: US20160259093A1
- Status: Published application
- Kind: A1
- Application number: 15/155,635
- Filed: 2016-05-16
- Published: 2016-09-08
- Earliest claimed: 2005-12-19
- Assignees: Essilor International (Compagnie Generale d'Optique)
- Applicants: Essilor International (Compagnie Generale D'Optique)
- Inventors: Dominique CONTE; Gérald FOURNAND; Agnès JALLOULI; Laurianne VAGHARCHAKIAN
- Web page: https://patentgrep.com/patent/US20160259093A1

## CPC

- B29D 11/00932: {Combined cutting and grinding thereof}
- G02B 1/18: Coatings for keeping optical surfaces clean, e.g. hydrophobic or photo-catalytic films (G02B1/16 takes precedence)
- B24B 9/146: {Accessories, e.g. lens mounting devices}
- B24B 13/005: Blocking means, chucks or the like; Alignment devices
- B29D 11/00865: {Applying coatings; tinting; colouring (printing, marking or copying processes B41M; identification in general G09F3/00; producing decorative effects in general B44C; positioning or marking of lenses B24B13/0055)}
- G02B 1/041: {Lenses}
- Y10T 428/265: 1 mil or less
- Y10T 428/31504: Composite [nonstructural laminate]
- B29D: PRODUCING PARTICULAR ARTICLES FROM PLASTICS OR FROM SUBSTANCES IN A PLASTIC STATE (making granules B29B9/00; making preforms B29B11/00)
- G02B: OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- B24B: MACHINES, DEVICES, OR PROCESSES FOR GRINDING OR POLISHING (grinding of gear teeth B23F, of screw-threads B23G1/36; by electro-erosion B23H; abrasive or related blasting B24C; tools for grinding, buffing or sharpening B24D; polishing compositions C09G1/00; abrasives C09K3/14; electrolytic etching or polishing C25F3/00; grinding arrangements for use on assembled railway tracks E01B31/17); DRESSING OR CONDITIONING OF ABRADING SURFACES; FEEDING OF GRINDING, POLISHING, OR LAPPING AGENTS
- Y10T: TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION

## Abstract

Methods for edging optical articles comprising two main faces, at least one of which being coated with an outermost layer comprising fixing the optical article to a chuck with a holding pad that adheres to both the optical article and the chuck, wherein the surface of the holding pad contacting the optical comprises an adhesive material; and edging the optical article with an edging device; wherein prior to fixing the optical article to the chuck, at least one temporary layer of an organic material is formed onto said outermost layer of the optical article, the organic material of the temporary layer comprising at least one organic compound having a fluorinated functional moiety and at least one linking functional moiety capable of establishing at least one intermolecular bond or interaction with the adhesive material of the holding pad. Optical articles obtained via these methods.

## Claims

### Claim 1

An optical article having two main faces, at least one of which is coated with an outermost layer, wherein at least one temporary layer of an organic material is formed on said outermost layer of said optical article, the organic material of the temporary layer comprising at least one organic compound having a fluorinated functional moiety, and a linking functional moiety; wherein said at least one temporary layer can be removed in a liquid medium and/or through mechanical action; and wherein said outermost layer of the optical article is an anti-fouling top coat.

### Claim 2 (depends on 1)

The optical article of claim 1, wherein said at least one organic compound has a main chain with two terminal positions, the first terminal position being occupied by the fluorinated functional moiety, and the second terminal position being occupied by the linking functional moiety.

### Claim 3

(canceled)

### Claim 4 (depends on 1)

The optical article of claim 1, wherein the anti-fouling top coat is a hydrophobic and/or oleophobic surface coating.

### Claim 5 (depends on 4)

The optical article of claim 4, wherein the hydrophobic and/or oleophobic surface coating is deposited on a mono- or multilayered anti-reflection coating or on a hard coating.

### Claim 6 (depends on 1)

The optical article of claim 1, wherein the fluorinated functional moiety is a linear perfluoroalkyl group with less than four carbon atoms.

### Claim 7 (depends on 1)

The optical article of claim 1, wherein the linking functional moiety is capable of establishing at least one intermolecular bond or interaction with an adhesive material of a holding pad.

### Claim 8 (depends on 7)

The optical article of claim 7, wherein the linking functional moiety is able to form at least one hydrogen bond with the adhesive material of said holding pad.

### Claim 9 (depends on 7)

The optical article of claim 7, wherein the adhesive material is a pressure sensitive adhesive (PSA).

### Claim 10 (depends on 1)

The optical article of claim 1, wherein the fluorinated functional moiety and the linking functional moiety are connected with a linking arm selected from the group consisting of:
alkylene groups, linear or branched, substituted or not substituted;
cycloalkylene groups, substituted or not substituted;
alkenylene or alkynylene groups, substituted or not substituted;
divalent heteroarylene groups, substituted or not substituted;
arylene groups, substituted or not substituted;
acyl(cyclo)alkylene groups, acyl(cyclo)alkenylene groups, acyl(cyclo)alkynylene groups, acyl(cyclo)arylene groups, the acyl function being —C(O)—;
acyloxy(cyclo)alkylene groups, acyloxy(cyclo)alkenylene groups, acyloxy(cyclo) alkynylene groups, acyloxy(cyclo)arylene groups, the acyloxy function being —C(O)O—;
oxy(cyclo)alkylene groups, oxy(cyclo)alkenylene groups, oxy(cyclo)alkynylene groups, oxy(cyclo)arylene groups;
thio(cyclo)alkylene groups, thio(cyclo)alkenylene groups, thio(cyclo)alkynylene groups, thio(cyclo)arylene groups, sulfo (—SO2—) derivatives thereof, sulfoxy (—S(O)—) derivatives thereof;
amino(cyclo)alkylene groups, amino(cyclo)alkenylene groups, amino(cyclo)alkynylene groups, amino(cyclo)arylene groups;
alkylamino(cyclo)alkylene groups, alkylamino(cyclo)alkenylene groups, alkylamino(cyclo) alkynylene groups, alkylamino(cyclo)arylene groups;
arylamino(cyclo)alkylene groups, arylamino(cyclo)alkenylene groups, arylamino(cyclo) alkynylene groups, arylamino(cyclo)arylene groups;
NHC(O), OC(O), C(O), NHS(O)2, NHS(O), OC(O)OC(O), C(O)C(O) groups, which may be connected to the fluorinated functional moiety (RF,H) group as defined below:
diorganosilylene groups, optionally substituted with an alkylene, arylene, alkenylene or alkynylene group; and
combinations of groups from the same or a different category.

### Claim 11 (depends on 1)

The optical article of claim 1, wherein the fluorinated functional moiety and the linking functional moiety are connected with a C1-C4 n-alkyl group.

### Claim 12 (depends on 1)

The optical article of claim 1, wherein the temporary layer imparts to the optical article a surface energy of at least 12 mJ/m2.

### Claim 13 (depends on 12)

The optical article of claim 12, wherein the temporary layer imparts to the optical article a surface energy of at least 15 mJ/m2.

### Claim 14 (depends on 1)

The optical article of claim 1, wherein the temporary layer imparts to the optical article a surface energy of 12 to 15 mJ/m2 and an hysteresis of the water contact angle of at least 8°.

### Claim 15 (depends on 14)

The optical article of claim 14, wherein the temporary layer imparts to the optical article a surface energy of 12 to 15 mJ/m2 and an hysteresis of the water contact angle of at least 9°.

### Claim 16 (depends on 15)

The optical article of claim 15, wherein the temporary layer imparts to the optical article a surface energy of 12 to 15 mJ/m2 and an hysteresis of the water contact angle of at least 10°.

### Claim 17 (depends on 1)

The optical article of claim 1, wherein the physical thickness of the temporary layer ranges from 5 to 50 nm.

### Claim 18 (depends on 1)

The optical article of claim 1, wherein the outermost layer of the optical article has a surface energy lower than or equal to 14 mJoules/m2.

### Claim 19 (depends on 1)

The optical article of claim 1, wherein the outermost layer of the optical article has a surface energy lower than or equal to 12 mJoules/m2.

### Claim 20 (depends on 1)

The optical article of claim 1, wherein said at least one temporary layer can be removed with one or more of an acidic aqueous solution having a molarity ranging from 0.01 to 1 N, a soapy aqueous solution, friction, wiping, and ultrasounds.

### Claim 21 (depends on 1)

The optical article of claim 1, wherein the anti-fouling top coat is obtained from a composition comprising a fluorosilane of formula:
wherein RF represents a perfluoroalkyl group, Z represents a fluorine atom or a trifluoromethyl group, a, b, c, d and e each independently represent 0 or an integer equal to or higher than 1, provided that a+b+c+d+e is not less than 1 and the order of the repeating units parenthesized by subscripts a, b, c, d and e occurring in the above formula is not limited to that shown; Y represents a hydrogen atom or an alkyl group containing 1 to 4 carbon atoms; X represents a hydrogen, bromine or iodine atom; R1 represents a hydroxyl group or a hydrolyzable substituent group; R2 represents a hydrogen atom or a monovalent hydrocarbon group; I represents 0, 1 or 2; m represents 1, 2 or 3; and n″ represents an integer equal to or higher than 1.