IP Library Granted Patent US 12,503,551
Granted Patent B2
US 12,503,551 · App. 17/649,566 · Granted Dec 23, 2025

Fluorine-containing isocyanul compound

Inventor: Masatoshi Nose (Cheonan-si, KR)
Assignee: DAIKIN INDUSTRIES, LTD.
C08G65/007C07D251/32C09D4/00C09D5/1662
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 12,503,551
App. No.
17/649,566
Granted
Dec 23, 2025
Kind
B2
Abstract

A compound of formula (I) having the structure shown below: wherein R B , R F1 , R A1 , X a and X b are as defined herein.

Claims (70)

1 . A compound of the following formula (1):

wherein:

R F1 is Rf 1 —R F —O q —;

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

R F is a divalent fluoropolyether group;

q is 0 or 1;

X a is a single bond or divalent organic group;

R A1 is —R A6 —R A4 —OR AC or —R A6 —R A5 —(OR AC ) 2 ;

R A4 is a C 1-10 alkylene group;

R A5 is a trivalent hydrocarbon group having 1 to 10 carbon atoms;

R A6 is a single bond or —C 1-10 alkylene-O—;

R Ac is a (meth)acryloyl group;

X b is —X c —X d —;

X c is —[(R c1 ) t1 —(X c1 ) t2 ]—X c2 —;

R c1 is each independently at each occurrence a single bond or a C 1-12 alkylene group;

X c1 is each independently at each occurrence O, NR x1 , S, SO, or SO 2 ;

R x1 is each independently at each occurrence a hydrogen atom or a C 1-6 alkyl group;

X c2 is O or NR x2 ;

R x2 is each independently at each occurrence a hydrogen atom or a C 1-6 alkyl group;

t1 is an integer of 1 to 6; and

t2 is an integer of 1 to 6,

wherein in [(R c1 ) t1 —(X c1 ) t2 ], the occurrence order of R c1 and X c1 is not limited in the formula;

X d is —CO—NR d2 —, —OCO—NR d2 —, —NR d2 —CO—, or —NR d2 —COO—;

R d2 is a hydrogen atom or a C 1-6 alkyl group; and

R B is R F1 —X a — or R A1 —X b —.

2 . The compound according to claim 1 ,

wherein R F is each independently a group of the formula:

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

wherein R Fa is each independently at each occurrence a hydrogen atom, a fluorine atom, or a chlorine atom; and

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 in parenthesis with a, b, c, d, e, or f, is not limited in the formula.

3 . The compound according to claim 2 , wherein R Fa is a fluorine atom.

4 . The compound according to claim 1 ,

wherein X a is a group of the following formula:

—(CX 121 X 122 ) x1 —(X a1 ) y1 —(CX 123 X 124 ) z1 —

wherein

X 121 to X 124 are each independently H, F, OH, or —OSi(OR 121 ) 3 , where three R 121 are each independently an alkyl group having 1 to 4 carbon atoms;

X a1 is —C(═O)NH—, —NHC(═O)—, —O—, —C(═O)O—, —OC(═O)—, —OC(═O)O—, or —NHC(═O)NH—, wherein the left side of each bond is bonded to CX 121 X 122 ; and

x1 is an integer of 0 to 10, y1 is 0 or 1, and z1 is an integer of 1 to 10.

5 . The compound according to claim 1 ,

wherein X a is a group of —(CH 2 ) m22 —, wherein m22 is an integer of 1 to 3.

6 . The compound according to claim 1 ,

wherein R A1 is —R A4 —OR AC or —R A5 —(OR AC ) 2 ;

R A4 is a C 1-10 alkylene group;

R A5 is a trivalent hydrocarbon group having 1 to 10 carbon atoms; and

R AC is a (meth)acryloyl group.

7 . The compound according to claim 1 ,

wherein X b is —X c —X d —;

X c is each independently at each occurrence O, NR x1 , S, SO, or SO 2 ;

X d is —CO—NR d2 —, —OCO—NR d2 —, —NR d2 —CO—, or —NR d2 —COO—; and

R d2 is a hydrogen atom or a C 1-6 alkyl group.

8 . The compound according to claim 1 ,

wherein R A1 is —R A5 —(OR AC ) 2 ;

R A5 is a trivalent hydrocarbon group having 4 to 6 carbon atoms; and

R AC is a (meth)acryloyl group.

9 . The compound according to claim 1 ,

wherein X c is —R cl′ —X c1 —R c1 ″—X c2 —;

R c1′ is a C 1-6 alkylene group;

R cl″ is a C 1-12 alkylene group;

X c1 is O, NR x1 , S, SO, or SO 2 ;

R x1 is each independently at each occurrence a hydrogen atom or a C 1-6 alkyl group;

X c2 is O or NR x2 ; and

R x2 is each independently at each occurrence a hydrogen atom or a C 1-6 alkyl group.

10 . The compound according to claim 1 ,

wherein X c is —R c1′ —X c1 —R c1″ —X c2 —;

R c1″ is a C 2-4 alkylene group;

R c1″ is a C 2-12 alkylene group;

X c1 is S; and

X c2 is O.

11 . The compound according to claim 1 ,

wherein R B is R A1 —X b —.

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 Feb 1, 2022
From: NOSE, MASATOSHI
To: DAIKIN INDUSTRIES, LTD.
Reel/Frame 058842/0294 →
Priority Claims (4)
JP 2019-143218 · Aug 2, 2019 · national
JP 2019-165215 · Sep 11, 2019 · national
JP 2019-228924 · Dec 19, 2019 · national
JP 2020-076866 · Apr 23, 2020 · national
Continuity (2)
Continuation PCTJP2020029570 · Jul 31, 2020
Related Publication 20220204690A1 · Jun 30, 2022
References Cited (8)
US 20040181008A1 · Hanazawa et al. · 2004 [cited by applicant]
US 20200024241A1 · Yamashita et al. · 2020 [cited by applicant]
WO 03002628A1 · 2003 [cited by applicant]
WO 2018056413A1 · 2018 [cited by applicant]
WO WO2018056413 · 2018 [cited by examiner]
International Search Report for PCT/JP2020/029570 dated Oct. 20, 2020 (PCT/ISA/210). [cited by applicant]
International Preliminary Report on Patentability dated Feb. 8, 2022 with a Translation of the Written Opinion of the International Searching Authority in Application No. PCT/JP2020/029570. [cited by applicant]
Extended European Search Report dated May 31, 2023 in European Application No. 20850700.4. [cited by applicant]