IP Library Granted Patent US 12,391,798
Granted Patent B2
US 12,391,798 · App. 17/647,057 · Granted Aug 19, 2025

Fluoropolyether group-containing silane compound

Inventors: Hideyuki Ikeuchi (Osaka, JP); Masato Naitou (Osaka, JP); Motoshi Matsui (Osaka, JP); Takashi Nomura (Osaka, JP)
Assignee: DAIKIN INDUSTRIES, LTD.
C08G65/336C08G65/333C07F7/081C07F7/1804C07F7/188C09D5/1625
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Quick Facts
Patent No.
US 12,391,798
App. No.
17/647,057
Granted
Aug 19, 2025
Kind
B2
Abstract

A fluoropolyether group-containing silane compound of the formula (1a) or the formula (1b), the symbols of which are as defined herein: R F1 —X A —R Si   (1a) R Si —X A —R F2 —X A —R Si   (1b).

Claims (69)

1. A fluoropolyether group-containing silane compound of the formula (Ia) or the formula (Ib):

R F1 —X A —R Si   (1a)

R Si —X A —R F2 —X A —R Si   (1b)

wherein

R F1 is each independently at each occurrence Rf 1 —R F —O q —;

R F2 is —Rf 2 p —R F —O g —;

Rf 1 is each independently at each occurrence a C 1-16 alkyl group optionally substituted with one or more fluorine atoms;

Rf 2 is a C 1-6 alkylene group optionally substituted with one or more fluorine atoms;

R F is each independently at each occurrence a divalent fluoropolyether group;

p is 0 or 1;

q is each independently at each occurrence 0 or 1;

X A is each independently at each occurrence —X 1 r1 —W—X 2 r2 —;

X 1 is a divalent organic group;

W is a 5-membered heterocyclic ring having two or more heteroatoms;

at least one of the heteroatoms is a N atom;

X 2 is a divalent organic group;

r1 is 0 or 1;

r2 is 0 or 1;

R Si is each independently at each occurrence represented by the formula (S1):

-A 1 (Z 1 —Si R 11 n R 12 3-n ) m R e 3-m   (S1)

A 1 is C or Si;

Z 1 is each independently at each occurrence a divalent organic group;

R 11 is each independently at each occurrence a hydroxyl group or a hydrolyzable group;

R 12 is each independently at each occurrence a hydrogen atom or a monovalent organic group;

n is each independently at each occurrence an integer of 1 to 3;

R e is each independently at each occurrence a hydrogen atom, a hydroxyl group, or a monovalent organic group; and

m is each independently at each occurrence 2 or 3.

2. The fluoropolyether group-containing silane compound according to claim 1 , wherein R F is each independently at each occurrence a group represented by the formula:

—(OC 6 F 12 ) a —(OC 5 F 10 ) b —(OC 4 F 8 ) c —(OC 3 F 6 ) d —(OC 2 F 4 ) e —(OCF 2 ) f —

wherein

a, b, c, d, e and f are each independently an integer of 0 to 200, the sum of a, b, c, d, e and f is 1 or more, and the occurrence order of the respective repeating units enclosed in parentheses provided with a, b, c, d, e or f is not limited in the formula.

3. The fluoropolyether group-containing silane compound according to claim 1 , wherein R F is each independently at each occurrence represented by the following formula (f1), (f2), (f3), (f4), or (f5):

—(OC 3 F 6 ) d —  (f1)

wherein d is an integer of 1 to 200;

—(OC 4 F 8 ) c —(OC 3 F 6 ) d —(OC 2 F 4 ) e —(OCF 2 ) f —  (f2)

wherein c and d are each independently an integer of 0 or more and 30 or less, e and f are each independently an integer of 1 or more and 200 or less;

the sum of c, d, e, and f is 2 or more; and

the occurrence order of the respective repeating units enclosed in parentheses provided with a subscript c, d, e, or f is not limited in the formula;

—(R 6 —R 7 ) g —  (f3)

wherein R 6 is OCF 2 or OC 2 F 4 ;

R 7 is a group selected from OC 2 F 4 , OC 3 F 6 , OC 4 F 8 , OC 5 F 10 , and OC 6 F 12 , or a combination of two or three groups independently selected from these groups; and

g is an integer of 2 to 100;

—(OC 6 F 12 ) a —(OC 5 F 10 ) b —(OC 4 F 8 ) c —(OC 3 F 6 ) d —(OC 2 F 4 ) e —(OCF 2 ) f —  (f4)

wherein e is an integer of 1 or more and 200 or less, a, b, c, d, and f are each independently an integer of 0 or more and 200 or less, the sum of a, b, c, d, e, and f is at least 1, and the occurrence order of the respective repeating units enclosed in parentheses provided with a, b, c, d, e, or f is not limited in the formula; and

—(OC 6 F 12 ) a —(OC 5 F 10 ) b —(OC 4 F 8 ) c —(OC 3 F 6 ) d —(OC 2 F 4 ) e —(OCF 2 ) f —  (f5)

wherein f is an integer of 1 or more and 200 or less, a, b, c, d, and e are each independently an integer of 0 or more and 200 or less, the sum of a, b, c, d, e, and f is at least 1, and the occurrence order of the respective repeating units enclosed in parentheses provided with a, b, c, d, e, or f is not limited in the formula.

4. The fluoropolyether group-containing silane compound according to claim 1 , wherein the two or more heteroatoms are two or more N atoms.

5. The fluoropolyether group-containing silane compound according to claim 1 , wherein the two or more heteroatoms are at least one N atom and at least one heteroatom other than N atom.

6. The fluoropolyether group-containing silane compound according to claim 5 , wherein the at least one heteroatom other than N atom is O atom.

7. The fluoropolyether group-containing silane compound according to claim 1 , wherein X 1 and X 2 are each independently at each occurrence a divalent organic group represented by —(R 51 ) p5 —(X 51 ) q5 —:

wherein

R 51 represents —(CH 2 ) s5 —;

s5 is an integer of 1 to 20;

X 51 represents-(X 52 ) l5 —;

X 52 each independently at each occurrence represents a group selected from the group consisting of —O—, —C(O)O—, —CONR 54 —, —O—CONR 54 —, and —NR 54 —;

R 54 each independently at each occurrence represents a hydrogen atom, a phenyl group, or a C 1-6 alkyl group;

l5 is an integer of 1 to 10;

p5 is 0 or 1; and

q5 is 0 or 1, provided that the occurrence order of respective repeating units enclosed in parentheses provided with p5 or q5 is not limited.

8. The fluoropolyether group-containing silane compound according to claim 1 , wherein X 1 and X 2 are each independently at each occurrence a C 1-20 alkylene group.

9. The fluoropolyether group-containing silane compound according to claim 1 , wherein r1 is 0 and r2 is 1.

10. The fluoropolyether group-containing silane compound according to claim 1 , wherein r1 is 0, r2 is 1, X 2 is —(CH 2 ) s5 —, and s5 is an integer of 1 to 3.

11. The fluoropolyether group-containing silane compound according to claim 1 , wherein Z 1 is

a C 1-6 alkylene group,

—(CH 2 ) z1 —O—(CH 2 ) z2 , or

—(CH 2 ) z3 -phenylene-(CH 2 ) z4 —,

wherein z1 to z4 are each independently an integer of 0 to 6.

12. The fluoropolyether group-containing silane compound according to claim 1 , wherein m is 3.

13. The fluoropolyether group-containing silane compound according to claim 1 , wherein n is 3.

Assignments (2)
CHANGE OF ADDRESS Recorded Jan 11, 2023
From: DAIKIN INDUSTRIES LTD.
To: DAIKIN INDUSTRIES LTD.
Reel/Frame 062355/0697 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 5, 2022
From: IKEUCHI, HIDEYUKI; NAITOU, MASATO; MATSUI, MOTOSHI; NOMURA, TAKASHI
To: DAIKIN INDUSTRIES, LTD.
Reel/Frame 058555/0665 →
Priority Claims (1)
JP 2019-176062 · Sep 26, 2019 · national
Continuity (2)
Continuation PCTJP2020034141 · Sep 9, 2020
Related Publication 20220127418A1 · Apr 28, 2022
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