Fluorine compounds
The present invention relates to novel compounds containing fluorinated end groups and to the use thereof in, for example, dirt-repellent coatings.
1. A compound of formulae (I′)
(Rf—CHF—CF 2 —S—CHR) m -L-(X) n (I′)
wherein
Rf=a perfluorinated alkyl group, optionally containing heteroatoms,
R=H or an alkyl group,
L is a single bond or a saturated, branched or unbranched alkylene group which optionally contains functional groups,
X is an acrylate group, a methacrylate group, an alkoxysilane group, a silanol group or a halosilane group,
m is ≥1, and
n is ≥1.
2. The compound according to claim 1 , wherein Rf is CF 3 —(CF 2 ) 0-3 —, CF 3 —(CF 2 ) 0-3 —O—, CF 3 —(CF 2 ) 0-3 —O—(CF 2 ) 1-3 —, CF 3 —(CF 2 ) 0- 3 —O—(CF 2 ) 1-3 —O—, CF 3 —(CF 2 ) 0-3 —O—(CF 2 ) 1-3 —O—CF 2 —, CF 3 —(CF 2 ) 0-3 —O—(CF 2 —O) 1-8 —, or CF 3 —(CF 2 ) 0-3 —O—(CF 2 —O) 1-8 —CF 2 —.
3. The compound according to claim 1 , wherein Rf is CF 3 —(CF 2 ) 1-2 —, CF 3 —(CF 2 ) 1-2 —O—, CF 3 —O—(CF 2 ) 1-3 —, CF 3 —O—(CF 2 ) 1-2 —O—, CF 3 —(CF 2 ) 1-2 —O—CF 2 —, CF 3 —O—(CF 2 ) 1-2 —O—CF 2 —, CF 3 —O—(CF 2 —O) 1-8 —, or CF 3 —O—(CF 2 —O) 1-8 —CF 2 —.
4. The compound according to claim 1 , wherein R is H or C 1 -C 3 alkyl.
5. The compound according to claim 1 , wherein R is H or a methyl group.
6. The compound according to claim 1 , wherein X is —SiR′ 3 in which R′ in each case, independently of one another, is alkyl, OH, halogen, alkoxy or aryloxy, and at least one R′ is not an alkyl group.
7. The compound according to claim 6 , wherein R′ is an alkoxy group OR″ in which R″ is C 1 -C 4 -alkyl.
8. The compound according to claim 7 , wherein R″ is C 1 - or C 2 -alkyl.
9. The compound according to claim 1 , wherein m and n, independently of one another, are each to 1-3.
10. The compound according to claim 1 , wherein said compound is of formulae (I′a) to (I′h)
wherein
Rf=a perfluorinated alkyl group, optionally containing heteroatoms,
R″=C 1 -C 4 -alkyl, and
R′″=H or an alkyl group, and
R 1 =H or C 1 -C 4 -alkyl.
11. The compound according to claim 10 , wherein Rf is CF 3 —(CF 2 ) 1-2 —, CF 3 —(CF 2 ) 1-2 —O—, CF 3 —O—(CF 2 ) 1-3 — or CF 3 —O—(CF 2 ) 1-2 —O—.
12. The compound according to claim 1 , wherein
Rf is CF 3 —(CF 2 ) 1-2 —, CF 3 —(CF 2 ) 1-2 —O—, CF 3 —O—(CF 2 ) 1-3 —, CF 3 —O—(CF 2 ) 1-3 —O—, CF 3 —(CF 2 ) 1-2 —O—CF 2 —, CF 3 —O—(CF 2 ) 1-2 —O—CF 2 —, CF 3 —O—(CF 2 O) 1-8 — or CF 3 —O—(CF 2 —O) 1-8 —CF 2 —;
R is H or CH 3 ;
L is a single bond or a C 1 -C 4 -alkylene group, which is optionally branched and optionally contains a functional group;
X is an alkoxysilane group —Si(OR″ 3 ) 3 ;
R″ is C 1 - or C 2 -alkyl;
m is 1 or 2; and
n is 1.
13. The compound according to claim 1 , wherein
Rf is CF 3 —(CF 2 ) 1-2 —, CF 3 —(CF 2 ) 1-2 —O—, CF 3 —O—(CF 2 ) 1-3 —, CF 3 —O—(CF 2 ) 1-3 —O—, CF 3 —(CF 2 ) 1-2 —O—CF 2 —, CF 3 —O—(CF 2 ) 1-2 —O—CF 2 —, CF 3 —O—(CF 2 O) 1-8 — or CF 3 —O—(CF 2 —O) 1-8 —CF 2 —;
R is H or CH 3 ;
L is a single bond or a C 1 -C 4 -alkylene group, which is optionally branched and optionally contains one or more heteroatoms a functional group, or both one or more heteroatoms and a functional group;
m is 1 or 2; and
n is 1.
14. The compound according to claim 1 , wherein said compound is selected from the following compounds:
15. A method of providing a dirt-repellent surface to a substrate comprising applying to said substrate at least one compound according to claim 1 .
16. A process for the degradation of a fluorine-containing compound according to claim 1 , said process comprising:
a) biological degradation, an abiotic degradation, or both a biological and abiotic degradation of the carbon skeleton of the fluorine-containing compound with formation of fluorine-containing compound,
b) conversion of the fluorine-containing compound formed in a) into a gas phase,
c) degradation of the fluorine-containing compound from compounds formed in b) into a low-molecular-weight compound by UV irradiation in the gas phase,
d) conversion of the low-molecular-weight compound formed in c) from the gas phase into a liquid phase, a solid phase, or both liquid and solid phases, and
e) mineralization of the low-molecular-weight compounds from d) in the liquid phase, solid phase, or both the liquid and solid phases.
17. A composition comprising at least one compound according to claim 1 and a support which is suitable for the respective application and optionally further additives.
18. A coated article having a whose coating has been produced using at least one compound according to claim 1 .
19. A process for the preparation of a compound of formula (F) according to claim 1 , said process comprising:
a) reacting a perfluoroalkyl vinyl ether of the formula Rf—CF═CF 2 with a mercaptoalcohol of the formula (HS)x-alkyl-(OH)y to obtain a compound of the formula (Rf—CHF—CF 2 —S) x -alkyl-(OH) y , and
b) reacting the compound prepared in a) with an unsaturated acid or acid anhydride, where Rf is a perfluorinated alkyl group, optionally containing heteroatoms, and x and y are, independently of one another, ≥1.