IP Library Granted Patent US 12,071,511
Granted Patent B2
US 12,071,511 · App. 17/331,096 · Granted Aug 27, 2024

Polyether group-containing compound

Inventors: Tsuneo Yamashita (Osaka, JP); Takashi Nomura (Osaka, JP); Kaori Ozawa (Osaka, JP); Hisashi Mitsuhashi (Osaka, JP)
Assignee: DAIKIN INDUSTRIES, LTD.
C08G65/336C07D251/46C07D251/52C07F7/1876C08G65/333C08G65/3348C08G77/46C07F7/0812
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Quick Facts
Patent No.
US 12,071,511
App. No.
17/331,096
Granted
Aug 27, 2024
Kind
B2
Abstract

A polyether group-containing compound of the formula (I). In each of the compound of the formula (I), one or two R— are represented by (Rf-X f1 -PE-X f2 ) α —X 1 —, and one or two R— are represented by R Si —. The symbols are as defined in the description.

Claims (116)

1. A polyether group-containing compound of the formula (I):

wherein

one or two R— groups are represented by (Rf-X f1 -PE-X f2 ) α —X 1 —, and one or two R— groups are represented by R Si —;

the total number of (Rf-X f1 -PE-X f2 ) α —X 1 — and R Si — is 3;

α is an integer of 1 to 9;

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

PE is each independently at each occurrence a group represented by formula: —(OC 6 F 12 ) a —(OC 5 F 10 ) b —(OC 4 F 8 ) c —(OC 3 X 10 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 or more and 200 or less, the sum of a, b, c, d, e, and f is at least 1, 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 X 10 is each independently at each occurrence a hydrogen atom, a fluorine atom, or a chlorine atom;

X f1 is represented by (X f11 ) z ;

X f11 is an alkylene group having 1 to 6 carbon atoms wherein a hydrogen atom is optionally replaced with a fluorine atom;

z is each independently at each occurrence 0 or 1;

X f2 is represented by (O) y or (NH) y ;

y is each independently at each occurrence 0 or 1;

X 1 is each independently at each occurrence (—(R 11 ) n16 —) 2 N—(R 12 ) n17 —, —(R 11 ) n16 —X 11 —, or —R 13 —,

R 11 each independently at each occurrence represents —(CH 2 ) n11 —, an o-, m-, or p-phenylene group which may be substituted with one or more fluorine atoms;

n11 is an integer of 1 to 20;

R 12 each independently at each occurrence represents —(CH 2 ) n12 —, an o-, m-, or p-phenylene group which may be substituted with one or more fluorine atoms;

n12 is an integer of 1 to 20;

X 11 is each independently at each occurrence —O—, —(OR 61 ) n14 —, —S—, —C(═O)—, —C(═O)O—, —O—C(═O)—, —O—C(═O)—O—, —Si(R 62 ) 2 —, —(Si(R 62 ) 2 O) n15 —Si(R 62 ) 2 —, —NR 3 C(═O)—, —C(═O)NR 3 —, —NR 3 C(═O)NR 3 —, —NR 3 C(═O)O—, —O—C(═O)NR 3 —, —NR 3 _, —SO 2 NR 3 —, or —SO 2 —;

R 61 is each independently at each occurrence a C 1-6 alkylene group;

n14 is each independently at each occurrence an integer of 1 to 5;

R 62 is each independently at each occurrence a phenyl group, a C 1-6 alkyl group, or a C 1-6 alkoxy group;

n15 is each independently at each occurrence an integer of 1 to 100;

R 3 is each independently at each occurrence a hydrogen atom, a phenyl group, or an alkyl group having 1 to 6 carbon atoms;

n16 each independently at each occurrence is 0 or 1;

n17 is 0 or 1;

R 13 is each independently at each occurrence —(CH 2 ) n13 —;

n13 is an integer of 1 to 20;

R Si — is each independently at each occurrence represented by any of the following formulae (A1) to (A4):

(R a m 1R b 3-m 1Si) β2 —X a3 —  (A2)

(R f3 p3 R f2 p2 R f1 p1 Si) β3 —X a4 —  (A3)

(R g3 q3 R g2 q2 R g1 q1 C) β4 —X a5 —  (A4)

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

R b is each independently at each occurrence a hydrogen atom or an alkyl group having 1 to 20 carbon atoms;

m1 is each independently at each occurrence an integer of 0 to 3;

X a1 , X a3 , X a4 , and X a5 are each independently at each occurrence (—(R 71 ) n21 —) 2 N—(R 72 ) n22 —, —(R 71 ) n21 —X 3 —(R 72 ) n22 —, —R 73 —, or —Y—O—;

R 71 is each independently at each occurrence —(CH 2 ) n23 —, an o-, m-, or p-phenylene group, which may be substituted with one or more fluorine atoms;

n23 is each independently at each occurrence an integer of 1 to 20;

R 72 is each independently at each occurrence —(CH 2 ) n24 —, an o-, m-, or p-phenylene group, which may be substituted with one or more fluorine atoms;

n24 is each independently at each occurrence an integer of 1 to 20;

n21 is each independently at each occurrence 0 or 1;

n22 is each independently at each occurrence 0 or 1;

the sum of n21 and n22 is 1 or more;

X 3 is each independently at each occurrence —O—, —(OR 74 ) n25 —, —S—, —C(═O)—, —C(═O)O—, —O—C(═O)—, —O—C(═O)—O—, —Si(R 75 ) 2 —, —(Si(R 75 ) 2 O) n26 —Si(R 75 ) 2 —, —NR 3 C(═O)—, —C(═O)NR 3 —, —NR 3 C(═O)NR 3 —, —NR 3 C(═O)O—, —O—C(═O)NR 3 —, —NR 3 —, —SO 2 NR 3 —, or —SO 2 —;

R 74 is each independently at each occurrence a C 1-6 alkylene group;

n25 is each independently at each occurrence an integer of 1 to 5;

R 75 is each independently at each occurrence a phenyl group, a C 1-6 alkyl group, or a C 1-6 alkoxy group;

n26 is each independently at each occurrence an integer of 1 to 100;

R 3 is each independently at each occurrence a hydrogen atom, a phenyl group, or an alkyl group having 1 to 6 carbon atoms;

R 73 is each independently at each occurrence —(CH 2 ) n27 —;

n27 is an integer of 1 to 20; and

Y is a di- to hexavalent hydrocarbon group and has a silicon atom and/or a siloxane bond;

X a2 is a single bond or a divalent organic group;

β1, β2, β3, and β4 are each independently at each occurrence an integer of 1 to 9;

t is each independently at each occurrence an integer of 2 to 10;

R 31 is each independently at each occurrence a hydrogen atom or a halogen atom;

R 32 is each independently at each occurrence a hydrogen atom or a monovalent organic group;

in formula (A1), there is at least one R a m 1R b 3-m 1Si— wherein m1 is 1 to 3, and in formula (A2), there is at least one R a m 1R b 3-m 1Si— wherein m1 is 1 to 3;

R f1 is each independently at each occurrence R 41 r1 R 42 r2 R 43 r3 Si-Z 1 —;

Z 1 is each independently at each occurrence an oxygen atom or a divalent organic group;

R 41 is each independently at each occurrence R f1 ′;

R f1 ′ has the same definition as that of R f1 ;

in R f1 , the number of Si atoms linearly connected via the group Z 1 is up to 5;

R 42 is each independently at each occurrence a hydroxyl group or a hydrolyzable group;

R 43 is each independently at each occurrence a hydrogen atom or a monovalent organic group;

r1 is each independently at each occurrence an integer of 0 to 3;

r2 is each independently at each occurrence an integer of 0 to 3;

r3 is each independently at each occurrence an integer of 0 to 3;

in each R 41 f1 R 42 f2 R 43 f3 Si-Z 1 —, the sum of r1, r2, and r3 is 3;

R f2 is each independently at each occurrence a hydroxyl group or a hydrolyzable group;

R f3 is each independently at each occurrence a hydrogen atom or a monovalent organic group;

p1 is each independently at each occurrence an integer of 0 to 3;

p2 is each independently at each occurrence an integer of 0 to 3;

p3 is each independently at each occurrence an integer of 0 to 3;

in each R f3 p3 R f2 p2 R f1 p1 Si—, the sum of p1, p2, and p3 is 3, and in formula (A3), there are at least two Si atoms to which a hydroxyl group or a hydrolyzable group binds;

R g1 is each independently at each occurrence R 51 s1 R 52 s2 R 53 s3 C-Z 2 —;

Z 2 is each independently at each occurrence an oxygen atom or a divalent organic group;

R 51 is each independently at each occurrence R g1 ′;

R g1 ′ has the same definition as that of R g1 ;

in R g1 , the number of C atoms linearly connected via the group Z 2 is up to 5;

R 52 is each independently at each occurrence R a m 1R b 3-m 1Si-Z 3 —;

Z 3 is each independently at each occurrence an oxygen atom or a divalent organic group;

R 53 is each independently at each occurrence a hydrogen atom, a hydroxyl group, or a monovalent organic group;

s1 is each independently at each occurrence an integer of 0 to 3;

s2 is each independently at each occurrence an integer of 0 to 3;

s3 is each independently at each occurrence an integer of 0 to 3;

in each R 51 s1 R 52 s2 R 53 s3 C-Z 2 —, the sum of s1, s2, and s3 is 3;

R g2 is each independently at each occurrence R a m 1R b 3-m 1Si-Z 4 —;

Z 4 is each independently at each occurrence an oxygen atom or a divalent organic group;

R g3 is each independently at each occurrence a hydrogen atom, a hydroxyl group, or a monovalent organic group;

q1 is each independently at each occurrence an integer of 0 to 3;

q2 is each independently at each occurrence an integer of 0 to 3; and

q3 is each independently at each occurrence an integer of 0 to 3;

in each R g3 q3 R g2 q2 R g1 q1 C—, the sum of q1, q2, and q3 is 3, and in formula (A4), there are at least two R a m 1R b 3-m 1Si— wherein m1 is 1 to 3.

2. The polyether group-containing compound according to claim 1 ,

wherein the sum of n16 and n17 is 1 or more.

3. The polyether group-containing compound according to claim 1 , wherein α is 2.

4. The polyether group-containing compound according to claim 1 , wherein α is 1.

5. The polyether group-containing compound according to claim 1 , wherein m1 is 2 or 3.

6. The polyether group-containing compound according to claim 1 , wherein m1 is 3.

7. The polyether group-containing compound according to claim 1 , wherein p1 is 3, and r2 is 3.

8. The polyether group-containing compound according to claim 1 , wherein in formula (A4), q2 is 3, and m1 is 3.

9. The polyether group-containing compound according to claim 1 , wherein β1, β2, β3, or β4 is 1.

10. The polyether group-containing compound according to claim 1 , wherein Rf is a perfluoroalkyl group having 1 to 16 carbon atoms.

11. The polyether group-containing compound according to claim 1 , wherein PE is a group represented by any of the following formulae (a) to (c):

—(OC 3 F 6 ) d —  (a)

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 —  (b)

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 an integer of 10 or more and 200 or less; 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; and

(R 6 —R 7 ) g —  (c)

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 is a combination of two or three groups selected from these groups; and

g is an integer of 2 to 100.

Assignments (3)
CHANGE OF ADDRESS Recorded Jan 11, 2023
From: DAIKIN INDUSTRIES LTD.
To: DAIKIN INDUSTRIES LTD.
Reel/Frame 062355/0740 →
CORRECTIVE ASSIGNMENT TO CORRECT THE ASSIGNEE NAME PREVIOUSLY RECORDED AT REEL: 056362 FRAME: 0224. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT . Recorded Jun 10, 2021
From: YAMASHITA, TSUNEO; NOMURA, TAKASHI; OZAWA, KAORI; MITSUHASHI, HISASHI
To: DAIKIN INDUSTRIES, LTD.
Reel/Frame 056541/0055 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 26, 2021
From: YAMASHITA, TSUNEO; NOMURA, TAKASHI; OZAWA, KAORI; MITSUHASHI, HISASHI
To: DAIKIN INDUSTRIES. LTD.
Reel/Frame 056362/0224 →
Priority Claims (1)
JP 2018-225935 · Nov 30, 2018 · national
Continuity (2)
Continuation PCTJP2019046418 · Nov 27, 2019
Related Publication 20210284798A1 · Sep 16, 2021