IP Library Granted Patent US 9,523,004
Granted Patent B2
US 9,523,004 · App. 13/508,870 · Granted Dec 20, 2016

Surface treatment composition, process for producing the same, and surface-treated article

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Quick Facts
Patent No.
US 9,523,004
App. No.
13/508,870
Granted
Dec 20, 2016
Kind
B2
Abstract

A surface treatment composition comprising (i) an organosilicon compound having an alkoxysilane functional group at the end of a fluorocontaining polyether chain and (ii) fluorocontaining polyether compound s, wherein a content of the fluorocontaining polyether compounds in the surface treatment composition is less than 25 mol % based on the surface treatment composition.

Claims (30)

1. A surface treatment composition comprising an organosilicon compound represented by the general formula (A):

F—(CF 2 ) q —(OC 3 F 6 ) m —(OC 2 F 4 ) n —(OCF 2 ) o —(CH 2 ) p —X—(CH 2 ) r —C 3 H 6 —Si(X′) 3-a (R 1 ) a   (A)

wherein q is an integer from 1 to 3; m, n, and o are independently integers from 0 to 200; p is 1 or 2; X is oxygen or a bivalent organic group; r is an integer from 0 to 17; R 1 is a C 1-22 linear or branched hydrocarbon group that does not have an unsaturated aliphatic bond; a is an integer from 0 to 2; and X′ is hydrolysable group,

wherein a total content of fluorine-containing compounds represented by the general formulas (B) and (C) in the surface treatment composition is less than 25 mol % based on the surface treatment composition, and wherein a content of the fluorine-containing compound represented by general formula (C) is at least 0.1 mol % based upon the surface treatment composition:

F—(CF 2 ) q —(OC 3 F 6 ) m —(OC 2 F 4 ) n —(OCF 2 ) o —F  (B)

wherein q, m, n and o are the same as described above,

F—(CF 2 ) q —(OC 3 F 6 ) m —(OC 2 F 4 ) n —(OCF 2 ) o —(CH 2 ) p —X—(CH 2 ) r —CH═CHCH 3   (C)

wherein q, m, n, o, p, r and X are the same as described above.

2. The surface treatment composition according to claim 1 , wherein, in the general formula (A), the hydrolysable group X′ is at least one selected from an alkoxy (—OR) group and an alkylamino group of (—NHR or —NR 2 ) wherein R is independently a C 1 -C 22 linear or branched alkyl group and two R groups may form a part of a cyclic amino group, and the integer a is 0.

3. The surface treatment composition according to claim 2 , wherein, in the general formula (A), the hydrolysable group X′ is an alkylamino group of (—NHR or —NR 2 ) wherein R is the same as described in claim 2 , and the integer a is 0.

4. The surface treatment composition according to claim 1 , wherein the organosilicon compound represented by the general formula (A) is represented by a general formula (i-d-i) or (i-d-ii):

F—(CF 2 ) q —(OC 3 F 6 ) m —(OC 2 F 4 ) n —(OCF 2 ) o —CH 2 O—(CH 2 ) r —C 3 H 6 —Si—(HNR) 3   (i-d-i)

or

F—(CF 2 ) q —(OC 3 F 6 ) m —(OC 2 F 4 ) n —(OCF 2 ) o —CH 2 O—(CH 2 ) r —C 3 H 6 —Si(NR 2 ) 3   (i-d-ii)

wherein q, m, n, o, r and R are the same as described in claim 1 , and fluorine-containing compounds represented by the general formulas (B) and (C) are represented respectively by general formulas (ii) and (i-c-d):

F—(CF 2 ) q —(OC 3 F 6 ) m —(OC 2 F 4 ) n —(OCF 2 ) o —F  (ii)

and

F—(CF 2 ) q —(OC 3 F 6 ) m —(OC 2 F 4 ) n —(OCF 2 ) o —CH 2 O—(CH 2 ) r —CH═CHCH 3   (i-c-d).

5. The surface treatment composition according to claim 1 , wherein the content of the fluorine-containing compound represented by the general formula (C) is 1.0 mol % or more and less than 25 mol % based on the surface treatment composition.

6. The surface treatment composition according to claim 1 , wherein the content of the fluorine-containing compounds represented by the general formulas (B) and (C) is less than 15 mol % based on the surface treatment composition.

7. The surface treatment composition according to claim 1 , wherein, in the general formulas (A) and (C), p is 1 and X is oxygen, that is, (A) and (C) are represented by the general formulas (i-d) and (i-c-d), respectively:

F—(CF 2 ) q —(OC 3 F 6 ) m —(OC 2 F 4 ) n —(OCF 2 ) o —CH 2 O—(CH 2 ) r —C 3 H 6 —Si(X′) 3-a (R 1 ) a   (i-d)

wherein q, m, n, o, r, a, X′ and R 1 are the same as described in claim 1 ,

F—(CF 2 ) q —(OC 3 F 6 ) m —(OC 2 F 4 ) n —(OCF 2 ) o —CH 2 O—(CH 2 ) r —CH═CHCH 3   (i-c-d)

wherein q, m, n, o and r are the same as described in claim 1 .

8. A surface-treated article, which comprises

a base material, and

a layer formed by applying the surface treatment composition according to claim 1 on a surface of the base material.

9. The surface-treated article according to claim 8 , wherein the base material is a transparent material comprising an antireflective optical layer.

10. The surface-treated article according to claim 8 which is selected from corrective and non-corrective lenses including single vision or multi-vision lenses like bifocal, trifocal and progressives lenses, which may be either segmented or non-segmented.

Assignments (9)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 6, 2018
From: ESSILOR INTERNATIONAL (COMPAGNIE GÉNÉRALE D'OPTIQUE)
To: ESSILOR INTERNATIONAL
Reel/Frame 045853/0275 →
CHANGE OF NAME Recorded Mar 29, 2018
From: DOW CORNING CORPORATION
To: DOW SILICONES CORPORATION
Reel/Frame 045381/0992 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 20, 2012
From: KLEYER, DON LEE
To: DOW CORNING CORPORATION
Reel/Frame 028993/0310 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 20, 2012
From: HUPFIELD, PETER CHESHIRE
To: DOW CORNING LIMITED
Reel/Frame 028993/0368 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 20, 2012
From: DOW CORNING LIMITED
To: DOW CORNING CORPORATION
Reel/Frame 028993/0387 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 20, 2012
From: HAYASHI, MASAYUKI
To: DOW CORNING TORAY CO., LTD.
Reel/Frame 028993/0454 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 20, 2012
From: DOW CORNING TORAY CO., LTD
To: DOW CORNING CORPORATION
Reel/Frame 028993/0472 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 20, 2012
From: YOSHIDA, TOMOHIRO; ITAMI, YASUO; MAEDA, MASAHIKO; MASUTANI, TETSUYA
To: DAIKIN INDUSTRIES, LTD.
Reel/Frame 028993/0601 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 20, 2012
From: HERVIEU, GREGORY; CALBA, PIERRE-JEAN
To: ESSILOR INTERNATIONAL
Reel/Frame 028993/0282 →