IP Library Granted Patent US 12,391,797
Granted Patent B2
US 12,391,797 · App. 17/692,474 · Granted Aug 19, 2025

Fluoropolyether group containing compound and method for producing the same

Inventors: Kentarou Hiraga (Osaka, JP); Akinari Sugiyama (Osaka, JP); Fumihiko Yamaguchi (Osaka, JP); Takashi Nomura (Osaka, JP); Shouta Shibutani (Osaka, JP); Shingo Okuno (Osaka, JP)
Assignee: DAIKIN INDUSTRIES, LTD.
C08G65/007C08G65/18C08G65/26C07C69/34C08G65/02
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Quick Facts
Patent No.
US 12,391,797
App. No.
17/692,474
Granted
Aug 19, 2025
Kind
B2
Abstract

A fluoropolyether-containing compound of the following formula (1a): R a —R 2 —R 1 —R b (1a) wherein the symbols are as defined in the specification. Also disclosed is a fluoropolyether-containing compound of the following formula (1b): R a —R 2′ —R 1 —R b (1b), as well as a method for producing a compound of the formula (A): FOC—R 2 —R 1 —COOR 12 (A) wherein the symbols are as defined in the specification.

Claims (47)

1. A fluoropolyether-containing compound of the following formula (1a):

wherein

R a is COF, COOR 11 , CH 2 OH, or CHO;

R b is COF, COOR 11 , CH 2 OH, or CHO;

wherein R a and R b are groups different from each other;

R 11 is each independently a hydrogen atom or an alkyl group having 1 to 6 carbon atoms optionally substituted with fluorine;

R 1 is a perfluoroalkylene group having 2 to 10 carbon atoms;

R 5a is CF 2 CF 2 CH 2 ;

R 6a is a linear alkylene group having 1 to 9 carbon atoms substituted with fluorine; and

n is an integer of 2 to 200.

2. The fluoropolyether-containing compound according to claim 1 ,

wherein R 6a is a linear alkylene group having 1 to 3 carbon atoms substituted with fluorine.

3. The fluoropolyether-containing compound according to claim 1 ,

wherein R 6a is a linear alkylene group having 2 carbon atoms substituted with fluorine.

4. The fluoropolyether group-containing compound according to claim 1 , wherein R a is COF, R b is COOR 11 , and R 11 is an alkyl group having 1 to 6 carbon atoms.

5. The fluoropolyether group-containing compound according to claim 1 , wherein R 1 is a perfluoroalkylene group having 2 to 6 carbon atoms.

6. A fluoropolyether-containing compound of the following formula (1b):

wherein

R a is COF, COOR 11 , CH 2 OH, or CHO;

R b is COF, COOR 11 , CH 2 OH, or CHO;

provided that

if R a is COF or COOR 11 , R b is CH 2 OH or CHO, or

if R b is COF or COOR 11 , R a is CH 2 OH or CHO;

R 11 is each independently a hydrogen atom or an alkyl group having 1 to 6 carbon atoms optionally substituted with fluorine;

R 1 is an a perfluoroalkylene group having 2 to 10 carbon atoms;

R 2′ is —R 6b —(OR 5b ) n —O—;

R 5b is CF 2 CF 2 CH 2 ;

R 6b is CF 2 CH 2 ; and

n is an integer of 2 to 200.

7. A method for producing a compound of the formula (A):

wherein

R 1 is a perfluoroalkylene group having 2 to 10 carbon atoms;

R 2 is —R 6 —(OR 5 ) n —O—;

R 5 is a linear alkylene group having 2 to 10 carbon atoms substituted with fluorine;

R 6 is a linear alkylene group having 1 to 9 carbon atoms substituted with fluorine;

R 12 is an alkyl group having 1 to 6 carbon atoms optionally substituted with fluorine; and

n is an integer of 2 to 200,

the method comprising:

reacting an acid fluoride compound of the formula (a):

wherein

R 13 is an alkylene group having 1 to 9 carbon atoms optionally substituted with fluorine; and

R 12 is an alkyl group having 1 to 6 carbon atoms optionally substituted with fluorine,

with a cyclic ether compound of the formula (b):

wherein R 15 is a linear alkylene group having 2 to 10 carbon atoms substituted with fluorine.

8. The production method according to claim 7 , wherein R 13 is a perfluoroalkylene group having 1 to 9 carbon atoms.

9. The production method according to claim 7 , wherein R 15 is a linear alkylene group having 2 to 4 carbon atoms substituted with fluorine.

10. The production method according to claim 7 , wherein R 15 is CF 2 CF 2 CH 2 .

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 Mar 11, 2022
From: HIRAGA, KENTAROU; SUGIYAMA, AKINARI; YAMAGUCHI, FUMIHIKO; NOMURA, TAKASHI; SHIBUTANI, SHOUTA; OKUNO, SHINGO
To: DAIKIN INDUSTRIES, LTD.
Reel/Frame 059244/0344 →
Priority Claims (2)
JP 2019-167534 · Sep 13, 2019 · national
JP 2020-008580 · Jan 22, 2020 · national
Continuity (2)
Continuation PCTJP2020032914 · Aug 31, 2020
Related Publication 20220235177A1 · Jul 28, 2022
References Cited (37)
US 3250808A · Milian, Jr. · 1966 [cited by examiner]
US 4131740A · England · 1978 [cited by examiner]
US 4138426A · England · 1979 [cited by examiner]
US 4247713A · England · 1981 [cited by examiner]
US 4334082A · Resnick · 1982 [cited by examiner]
US 4357282A · Anderson · 1982 [cited by examiner]
US 4390720A · Resnick · 1983 [cited by examiner]
US 4845268A · Ohsaka · 1989 [cited by examiner]
US 4904417A · Ohsaka · 1990 [cited by examiner]
US 4973742A · Ohsaka · 1990 [cited by examiner]
US 5506309A · Bierschenk · 1996 [cited by examiner]
US 5539059A · Bierschenk · 1996 [cited by examiner]
US 6136331A · Morita · 2000 [cited by examiner]
US 8513459B2 · Ikeda · 2013 [cited by examiner]
US 20010050351A1 · Saito et al. · 2001 [cited by applicant]
US 20070178133A1 · Rolland · 2007 [cited by applicant]
US 20100101245A1 · Bivens et al. · 2010 [cited by applicant]
US 20140123876A1 · Fontana · 2014 [cited by examiner]
US 20140135244A1 · Tonelli et al. · 2014 [cited by applicant]
US 20140243547A1 · Fontana · 2014 [cited by examiner]
JP 53132519A · 1978 [cited by applicant]
JP 60137928A · 1985 [cited by examiner]
JP 60202122A · 1985 [cited by examiner]
JP 2002037880A · 2002 [cited by applicant]
JP 2009161532A · 2009 [cited by examiner]
JP 2010254738A · 2010 [cited by examiner]
JP 2014517131A · 2014 [cited by applicant]
JP 2014520106A · 2014 [cited by examiner]
RU 2461599C2 · 2012 [cited by applicant]
WO WO9003410A1 · 1990 [cited by examiner]
WO WO0226686A1 · 2002 [cited by examiner]
WO WO0226687A1 · 2002 [cited by examiner]
WO WO2013042732A1 · 2013 [cited by examiner]
International Preliminary Report on Patentability with the translation of Written Opinion dated Mar. 24, 2022 from the International Bureau in International application No. PCT/JP2020/032914. [cited by applicant]
Extended European Search Report dated Jul. 27, 2023 in European Application No. 20864031.8. [cited by applicant]
E. J. Soloski, et al., “Synthesis of Perfluoro (Polyether) Difunctional Compounds”, Journal of Fluorine Chemistry, 1978, pp. 601-612, vol. 11 (12 pages total). [cited by applicant]
International Search Report for PCT/JP2020/032914 dated Nov. 17, 2020 [PCT/ISA/210]. [cited by applicant]