Fluorosurfactants

Patent metadata

Field	Value
Publication number	US-9481643-B2
Application number	US-201314416003-A
Country	US
Kind code	B2
Filing date	Jul 16, 2013
Priority date	Jul 18, 2012
Publication date	Nov 1, 2016
Grant date	Nov 1, 2016

Abstract

The present invention relates to novel compounds containing fluorinated end groups, to the use thereof as surface-active substances, and to compositions comprising these compounds.

First claim

The invention claimed is:

1. A compound of formula (I)
(R f -A a -C c ) n -(spacer) m -X o   (I)

wherein either a) or b) provides the definitions for the elements of formula (I)
a)
Rf=CF 3 —CF 2 —CF 2 —O—CF(CF 3 )—CH 2 —,
A=—O—CH 2 —CHR′—,
R′=H or alkyl,
C=alkylene, O, —OCO— or —NR″—,
R″=H, alkyl or (CH 2 CHR′″) m′ —R″″,
m′=an integer of 1 to 100,
R′″ and R″″=independently of one another, H or alkyl, in which one or more non-adjacent C atoms are optionally replaced by O or N,
spacer=a saturated or unsaturated, branched or unbranched hydrocarbon unit, optionally containing heteroatoms,
X=an anionic, cationic, non-ionic or amphoteric hydrophilic group,
non-ionic
hydrophilic
group=is R 4 —(O—CH 2 CHR 5 ) m″ —, —CH(OH)—CH 2 —NH-Sach, or —Y—(CH 2 —CH 2 —O) v —R 4′ ,
m″=an integer of 1 to 100,
R 4 and R 5 =independently of one another H or C 1 -C 4 -alkyl,
Sach=a sugar,
Y=S, O or NH,
R 4′ =H or alkyl and
v=1-100,
a=0 or 1, and a=1, if X=an anionic hydrophilic group,
n=2, 3, 4, 5 or 6,
c=0 or 1,
m=0 or 1, and
o=1, 2, 3 or 4, and o=0 if R″=—(CH 2 CHR′″) m′ —R″″, wherein R′″ and/or R″″=alkyl, wherein one or more non-adjacent C atoms have been replaced by O or N,
or
b)
Rf=CF 3 —CF 2 —CF 2 —O—CF(CF 3 )—CO—,
A=—O—CH 2 —CHR′—,
R′=H or alkyl,
C=alkylene, O, —OCO— or —NR″—,
R″=H, alkyl or (CH 2 CHR′″) m′ —R″″,
m′=an integer of 1 to 100,
R′″ and R″″=independently of one another, H or alkyl, in which one or more non-adjacent C atoms are optionally replaced by O or N,
spacer=a saturated or unsaturated branched or unbranched hydrocarbon unit, optionally containing heteroatoms,
X=an anionic, cationic, non-ionic or amphoteric hydrophilic group,
non-ionic
hydrophilic
group=is R 4 —(O—CH 2 CHR 5 ) m″ —, —CH(OH)—CH 2 —NH-Sach, or —Y—(CH 2 —CH 2 —O) v —R 4′ ,
m″=an integer of 1 to 100,
R 4 and R 5 =independently of one another H or C 1 -C 4 -alkyl,
Sach=a sugar,
Y=S, O or NH,
R 4′ =H or alkyl,
v=1-100,
a=0 or 1,
n=2, 3, 4, 5 or 6,
c=0 or 1,
m=1, and
o=1, 2, 3 or 4, and o=0 if R″=—(CH 2 CHR′″) m′ —R″″, wherein where R′″ and/or R″″=alkyl, wherein one or more non-adjacent C atoms have been replaced by O or N,
and wherein
the following compounds are excluded:
Rf′—O—CH 2 CH(OSO 3 Na)—CH 2 —O—CH 2 —CH—(C 2 H 5 )—C 4 H 9 ,
Rf′—O—CH 2 CH(OSO 3 H)—(CH 2 ) 5 —CH 3 ,
Rf′—O—CO—CH 2 —CH(OSO 3 Na)—CO—O—Rf′,
Rf″—CH 2 —CH(SO 3 Na)—Rf″,
Rf″—CH 2 —CH(CH 2 SO 3 Na)—Rf″ and
Rf″—CH—(CH 3 )CH(SO 3 Na)—Rf″,
wherein
Rf′=CF 3 CF 2 CF 2 —O—CF(CF 3 )—CH 2 —, and
Rf″=CF 3 CF 2 CF 2 —O—CF(CF 3 )—CO—NHCH 2 CH 2 —O—CO—.

2. The compound of claim 1 , wherein a) provides the definitions for the elements of formula (I), and wherein
R′=H or CH 3 ,
C=C 1 -C 4 -alkylene, O or —OCO—,
spacer=aliphatic or aromatic hydrocarbon unit, optionally containing Heteroatoms,
n=1, 2, or 3,
c=1, and
o=1 or 2.

3. A compound of claim 1 , wherein a) provides the definitions for the elements of formula (I), and which is of formula (II)

wherein
Rf=CF 3 —CF 2 —CF 2 —O—CF(CF 3 )—CH 2 —,
A=—O—CH 2 —CHR′—,
R′=H, CH 3 , C 2 H 5 ,
a=0 or 1,
X=an anionic, cationic non-ionic or amphoteric hydrophilic group,
non-ionic
hydrophilic
group=R 4 —(O—CH 2 CHR 5 ) m″ —,—CH(OH)—CH 2 —NH-Sach, or —Y—(CH 2 —CH 2 —O) v —R 4′ ,
m″=an integer of 1 to 100,
R 4 and R 5 =independently of one another H or C 1 -C 4 -alkyl,
Sach=a sugar,
Y=S, O or NH,
R 4′ =H or alkyl,
v=1-100,
R 1 =hydrogen or —CH 2 —COO—(A) a —Rf, and
R 2 =hydrogen, —CH 2 —COO—(A) a —Rf or X.

4. The compound of claim 3 , which is of formula (II-a):

wherein
Rf=CF 3 —CF 2 —CF 2 —O—CF(CF 3 )—CH 2 —,
A=—O—CH 2 —CHR′—,
R′=H, CH 3 , C 2 H 5 ,
a=0 or 1, and
X=as defined for the compound of formula (II).

5. The compound of claim 3 , which is of formula (II-b):

wherein
Rf=CF 3 —CF 2 —CF 2 —O—CF(CF 3 )—CH 2 —,
A=—O—CH 2 —CHR′—,
R′=H, CH 3 , C 2 H 5 ,
a=0 or 1, and
X=as defined for the compound of formula (II).

6. The compound of claim 3 , which is of formula (II-c):

wherein
Rf=CF 3 —CF 2 —CF 2 —O—CF(CF 3 )—CH 2 —,
A=—O—CH 2 —CHR′—,
R′=H, CH 3 , C 2 H 5 ,
a=0 or 1, and
X=as defined for the compound of formula (II).

7. The compound of claim 3 , which is of formula (II-d):

wherein a) provides the definitions for the elements of formula (I), and wherein
Rf=CF 3 —CF 2 —CF 2 —O—CF(CF 3 )—CH 2 —,
A=—O—CH 2 —CHR′—,
R′=H, CH 3 , C 2 H 5 ,
a=0 or 1, and
X=as defined for the compound of formula (II).

8. The compound of claim 1 , wherein b) provides the definitions for the elements of formula (I), and wherein characterised
C=NR″—,
R″=H, alkyl or —(CH 2 CHR″′) m′ —R″″,
m′=an integer of 1 to 100,
R′″=H or C 1 -C 4 -alkyl,
R″″=alkyl, in which one or more non-adjacent C atoms have been replaced by O,
spacer=linear or branched alkylene,
X=as defined for the compound of formula (I),
a=0,
n=2 or 3,
c=1,
m=1, and
o=1 or 2, and o=0 if R″=—(CH 2 CHR′″) m′ —R″″.

9. A compound of claim 1 , wherein b) provides the definitions for the elements of formula (I), and which is of formula (III)

wherein
Rf=CF 3 —CF 2 —CF 2 —O—CF(CF 3 )—CO— or =Rf′,
Rf′=CF 3 —CF 2 —CF 2 —O—CF(CF 3 )—CH 2 —O—CH 2 —CHR′—,
p=1-10,
q=1-10,
R′=H or alkyl,
R″=H, alkyl or (CH 2 CHR′″) m′ —R″″,
m′=an integer of 1 to 100,
R′″ and R″″=independently of one another, H or alkyl, in which one or more non-adjacent C atoms are optionally replaced by O or N,
D and D′=H or X, wherein at least one group is equal to X if R″=H or alkyl,
X=an anionic, cationic, non-ionic or amphoteric hydrophilic group,
non-ionic
hydrophilic
group=R 4 —(O—CH 2 CHR 5 ) m″ —, —CH(OH)—CH 2 —NH-Sach, or —Y—(CH 2 —CH 2 —O) v —R 4′ ,
m″=an integer of 1 to 100,
R 4 and R 5 =independently of one another H or C 1 -C 4 -alkyl,
Sach=a sugar,
Y=S, O or NH,
R 4′ =H or alkyl,
v=1-100.

10. The compound of claim 9 , wherein X is not —SO 3 − .

11. The compound of claim 9 , wherein
Rf=CF 3 —CF 2 —CF 2 —O—CF(CF 3 )—CO—, R″=H or alkyl and D and/or D′=X.

12. A compound of claim 1 , wherein a) provides the definitions for the elements of formula (I), and which is of claim 1 , formula (IV)
R f -A a -C-(spacer)mX  (IV)

wherein
Rf=CF 3 —CF 2 —CF 2 —O—CF(CF 3 )—CH 2 —,
A=—O—CH 2 —CHR′—,
R′=H or alkyl,
C=alkylene or O,
X=an anionic ,cationic non-ionic or amphoteric hydrophilic group,
non-ionic
hydrophilic
group=R 4 —(O—CH 2 CHR 5 ) m″ —, —CH(OH)—CH 2 —NH-Sach, or —Y—(CH 2 —CH 2 —O) v —R 4′ ,
m″=an integer of 1 to 100,
R 4 and R 5 =independently of one another H o

Assignees

• Merck Patent Gmbh

Inventors

• Friedrich Reiner
• Jonschker Gerhard
• Schooren Fanny
• Depner Christian
• Schellenberger Steffen

Classifications

• C07C43/12

  containing halogen · CPC title

• C07C19/08

  containing fluorine · CPC title

• C07C43/137

  containing halogen · CPC title

• C07C211/15

  the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups · CPC title

• C07C309/17 Primary

  containing carboxyl groups bound to the carbon skeleton · CPC title