IP Library Granted Patent US 10,689,522
Granted Patent B2
US 10,689,522 · App. 15/536,700 · Granted Jun 23, 2020

Fluorine compounds

Inventor: Reiner Friedrich (Seeheim-Jugenheim, DE)
Assignee: Merck Patent GmbH
C09D5/00C07C69/653C07F7/1804C09D4/00C09D183/08
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Quick Facts
Patent No.
US 10,689,522
App. No.
15/536,700
Granted
Jun 23, 2020
Kind
B2
Abstract

The present invention relates to compounds of the formula (I) (Rf-CHF—CF 2 —CHR) m -L-(X) n , where Rf=a perfluorinated alkyl group, optionally containing heteroatoms, R=H or an alkyl group, L=a single bond or a divalent organic group, X=an anchor group, m is ≥1 and n is ≥1, and to the use thereof in, for example, dirt-repellent coatings.

Claims (49)

1. A compound of the formula (I)

(Rf-CHF—CF 2 —CHR) m -L-(X) n   (I)

where

a)

Rf is a group selected from 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 and CF 3 —(CF 2 ) 0-3 —O—(CF 2 —O) 1-8 —CF 2 —

R=H or an alkyl group,

L=a single bond or a saturated, branched or unbranched alkylene group, optionally containing heteroatoms and/or functional groups,

X=an ethylenically unsaturated group, an alkoxysilane group, a silanol group or a halosilane group,

m is ≥1

and n is ≥1

or

b)

Rf is CF 3 —(CF 2 ) 0-3 —,

R=an alkyl group,

L=a single bond or a saturated, branched or unbranched alkylene group, optionally containing heteroatoms and/or functional groups,

X=an alkoxysilane group, a silanol group or a halosilane group,

m is ≥1

and n is ≥1,

or

c)

Rf is where CF 3 —(CF 2 ) 0-3 —O— the compounds conform to the formulae (III) to (VIII) where R″=C 1 -C 4 -alkyl and R′″=H or an alkyl group,

where R″=C1-C4-alkyl and R′″=H or an alkyl group.

2. A compound according to claim 1 , wherein Rf is CF 3 —(CF 2 ) 1-2 —O—, CF 3 —O—(CF 2 ) 1-2 —, 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 — and CF 3 —O—(CF 2 —O) 1-8 —CF 2 —.

3. A compound according to claim 1 , wherein R in a) is equal to H or C1-C3 alkyl.

4. A compound according to claim 1 , wherein R in a) is equal to H or a methyl group.

5. A compound according to claim 1 , wherein L is a saturated, branched or unbranched alkylene group, optionally containing heteroatoms and/or functional groups.

6. A compound according to claim 1 , wherein X is an ethylenically unsaturated group, an alkoxysilane group, or a halosilane group.

7. A compound according to claim 1 , wherein X is an acrylate or methacrylate group.

8. A compound according to claim 1 , wherein X is equal to —SiR′ 3 , where the groups R′ are, independently of one another, equal to alkyl, OH, halogen, alkoxy or aryloxy, where at least one group R′ is not an alkyl group.

9. A compound according to claim 8 , wherein

R′ an alkoxy group OR″, where R″ equal to C1-C4-alkyl.

10. A compound according to claim 9 , wherein

R″ is equal to C1- or C2-alkyl.

11. A compound according to claim 1 , wherein m and n, independently of one another, are equal to 1-3.

12. A compound according to claim 1 , of formulae

where Rf=a group selected from 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 — and CF 3 —(CF 2 ) 0-3 —O—(CF 2 —O) 1-8 —CF 2 —,

R″=C1-C4-alkyl and R′″=H or an alkyl group.

13. A compound according to claim 12 , wherein

Rf is equal to CF 3 —(CF 2 ) 1-2 —O—, CF 3 —O—(CF 2 ) 1-2 — or CF 3 —O—(CF 2 ) 1-3 —O—.

14. A compound according to claim 1 , that is

15. A composition comprising at least one compounds according to claim 1 and a support which is suitable for the respective application and optionally further additives.

16. A coated article whose coating has been produced using at least one compound according to claim 1 .

17. A method for the production of functional coatings and surface modifications, which comprises including a compound according to claim 1 in a functional coating or surface modification.

18. A process for the degradation of fluorine-containing compounds of claim 1 comprising the following steps:

a) biological and/or abiotic degradation of the carbon skeleton of the fluorine-containing compounds with formation of fluorine-containing compounds,

b) conversion of the fluorine-containing compounds formed in step a) into a gas phase,

c) degradation of the fluorine-containing compounds formed in step a) into low-molecular-weight compounds by UV irradiation in the gas phase,

d) conversion of the low-molecular-weight compounds formed in step c) from the gas phase into a liquid and/or solid phase,

e) mineralisation of the low-molecular-weight compounds formed in step c) in the liquid and/or solid phase.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 28, 2025
From: MERCK PATENT GMBH
To: SUSONITY COMMERCIAL GMBH
Reel/Frame 072287/0400 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 16, 2017
From: FRIEDRICH, REINER
To: MERCK PATENT GMBH
Reel/Frame 042729/0384 →
Priority Claims (1)
EP 14004336 · Dec 19, 2014 · regional
Continuity (1)
Related Publication 20170349761A1 · Dec 7, 2017