IP Library Granted Patent US 11,692,061
Granted Patent B2
US 11,692,061 · App. 16/944,864 · Granted Jul 4, 2023

Fluoro (poly) ether group-containing silane compound

Inventors: Hisashi Mitsuhashi (Osaka, JP); Takashi Nomura (Osaka, JP); Masato Naitou (Osaka, JP); Shinya Takano (Osaka, JP); Yuusuke Watanabe (Osaka, JP); Kaori Ozawa (Osaka, JP); Peter Hupfield (Dusseldorf, DE)
Assignee: DAIKIN INDUSTRIES, LTD.
C08G65/336C08G65/007C08G65/226C09D5/1675C09D171/02C09K3/18C08G77/46
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Quick Facts
Patent No.
US 11,692,061
App. No.
16/944,864
Granted
Jul 4, 2023
Kind
B2
Abstract

A fluoro(poly)ether group-containing silane compound represented by any of the formulae (A1), (A2), (B1), (B2), (C1), or (C2). In the formulae, PFPE is each independently at each occurrence a group represented by the formula: —(OC 3 F 6 ) d —, wherein the repeating unit OC 3 F 6 of the formula includes a branched structure, and d is an integer of 2 or more and 200 or less. The symbols are as defined in the description.

Claims (41)

1. A fluoro(poly)ether group-containing silane compound represented by any of the formulae (B1), and (B2):

Rf-PFPE—X 3 —SiR a k1   (B1)

R a k1 Si—X 3 —PFPE—X 3 —SiR a k1   (B2)

wherein:

Rf each independently at each occurrence represents an alkyl group having 1 to 16 carbon atoms which is optionally substituted by one or more fluorine atoms;

-PFPE-X 3 — represents —(OC 3 F 6 ) d —(OCF(CF 3 ))—X 10 —CONH—X 11 —, or —(OC 3 F 6 ) d —(OCF(CF 3 ))—X 10 —(OR 35 ) n4 —X 11 —;

—X 3 -PFPE-X 3 — represents —X 11 —NHCO—X 10 —(OC 3 F 6 ) d —(OCF(CF 3 ))—X 10 —CONH—X 11 —, or —X 11 —(R 35 O) n4 —X 10 —(OC 3 F 6 ) d —(OCF(CF 3 ))—X 10 —(OR 35 ) n4 —X 11 —;

wherein the repeating unit OC 3 F 6 of the formula has a branched structure, and d is an integer of 2 or more and 200 or less;

X 10 is each independently at each occurrence a single bond or R 36 ;

R 36 is a C 1-20 alkylene group which is optionally substituted by one or more fluorine atoms;

X 11 is each independently at each occurrence a C 1-20 alkylene group;

R 35 is each independently at each occurrence a C 1-6 unsubstituted alkylene group;

n4 is each independently at each occurrence an integer of 1 to 5;

R a each independently at each occurrence represents —Z 3 —SiR 72 3 ;

Z 3 each independently at each occurrence represents C 1-6 alkylene group;

R 72 each independently at each occurrence represents a hydroxyl group or a hydrolyzable group;

k1 is 3.

2. The fluoro(poly)ether group-containing silane compound according to claim 1 , wherein the repeating unit OC 3 F 6 in PFPE is represented by OCF(CF 3 )CF 2 , and

d is an integer of 2 or more and 200 or less.

3. The fluoro(poly)ether group-containing silane compound according to claim 1 , which is represented by the formula (B1).

4. A surface-treating agent comprising the fluoro(poly)ether group-containing silane compound according to claim 1 .

5. The surface-treating agent according to claim 4 , further comprising a solvent.

6. The surface-treating agent according to claim 4 , further comprising:

one or more other components selected from a fluorine-containing oil, a silicone oil, an alcohol, a catalyst, a transition metal, a halide ion, and a compound containing an atom with an unshared electron pair in a molecular structure.

7. The surface-treating agent according to claim 4 , which is used as an antifouling coating agent or a waterproof coating agent.

8. A pellet comprising the surface-treating agent according to claim 4 .

9. An article comprising:

a base material; and

a layer on a surface of the base material, the layer being formed of the surface-treating agent according to claim 4 .

10. The article according to claim 9 having a contact angle of water on a surface of 100 degrees or more,

wherein a ratio of a contact angle of water after irradiation to the contact angle is 83% or more, and

the contact angle of water after irradiation is a contact angle on the surface after irradiation with ultraviolet rays of 310 nm at an illumination intensity of 0.63 W/m 2 for 96 hours.

11. A compound represented by the formula (c1-3) or (c2-3):

wherein:

Rf each independently at each occurrence represents an alkyl group having 1 to 16 carbon atoms which is optionally substituted by one or more fluorine atoms;

-PFPE-X 10 — is represented by —(OCF(CF 3 )CF 2 ) d —(OCF(CF 3 ))—, or —(OCF(CF 3 )CF 2 ) d —(OCF(CF 3 ))—R 36 —;

—X 10 -PFPE-X 10 — is represented by —(OCF(CF 3 )CF 2 ) d —(OCF(CF 3 ))—, or —R 36 —(OCF(CF 3 )CF 2 ) d —(OCF(CF 3 ))—R 36 —;

d is an integer of 2 or more and 200 or less;

R 36 is a C1-20 alkylene group which is optionally substituted by one or more fluorine atoms;

X 11 is each independently at each occurrence a C 1-20 alkylene group which is optionally substituted by one or more fluorine atoms; and

Y 11 is each independently at each occurrence a single bond or C 1-4 alkylene group.

Assignments (2)
CHANGE OF ADDRESS Recorded Jan 11, 2023
From: DAIKIN INDUSTRIES LTD.
To: DAIKIN INDUSTRIES LTD.
Reel/Frame 062355/0740 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 31, 2020
From: MITSUHASHI, HISASHI; NOMURA, TAKASHI; NAITOU, MASATO; TAKANO, SHINYA; WATANABE, YUUSUKE; OZAWA, KAORI; HUPFIELD, PETER
To: DAIKIN INDUSTRIES, LTD.
Reel/Frame 053371/0628 →
Priority Claims (1)
JP 2018-017571 · Feb 2, 2018 · national
Continuity (2)
Continuation PCTJP2019003488 · Jan 31, 2019
Related Publication 20200354520A1 · Nov 12, 2020