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

Patent metadata

Field	Value
Publication number	US-9523004-B2
Application number	US-201013508870-A
Country	US
Kind code	B2
Filing date	Nov 10, 2010
Priority date	Nov 11, 2009
Publication date	Dec 20, 2016
Grant date	Dec 20, 2016

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.

First claim

The invention claimed is:

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.

Assignees

• Hervieu Gregory
• Calba Pierre-Jean
• Kleyer Don Lee
• Hayashi Masayuki
• Hupfield Peter Cheshire
• Yoshida Tomohiro
• Itami Yasuo
• Maeda Masahiko
• Masutani Tetsuya
• Essilor Int
• Dow Corning
• Daikin Ind Ltd

Inventors

• Hervieu Gregory
• Calba Pierre-Jean
• Kleyer Don Lee
• Hayashi Masayuki
• Hupfield Peter Cheshire
• Yoshida Tomohiro
• Itami Yasuo
• Maeda Masahiko
• Masutani Tetsuya

Classifications

• C09D5/1675

  Polyorganosiloxane-containing compositions · CPC title

• C09D5/006 Primary

  Anti-reflective coatings · CPC title

• Y10T428/31663

  As siloxane, silicone or silane · CPC title