Fluorinated aryl epoxide compounds
View Patent ↗A fluorinated aromatic epoxy compound having a fluorinated ether tail and a pendant epoxy functional group. These compounds are particularly useful as starting materials for producing various water and oil repellents and soil resists.
1. A compound represented by the following Formula (I):
wherein
R f is —CF 3 , —C 2 F 5 , or —CF 2 CFXCF 3 ;
X is —F, or —OC 3 F 7 ;
Y is —H, —Cl, or —Br;
each R is independently, —H, or C 1 to C 10 alkyl;
R v is —H, or C 1 to C 10 alkyl;
R w is —H, or C 1 to C 10 alkyl;
R x is —H, C 1 to C 10 alkyl;
R y is —H, C 1 to C 10 alkyl;
R z is —H, C 1 to C 10 alkyl;
Z is selected from the group consisting of
wherein each R is independently selected from —H or a C 1 to C 10 alkyl;
a is an integer from 1 to 5;
b is an integer from 1 to 5;
c is 0 or 1;
d is an integer from 1 to 10;
m is an integer from 1 to 10;
n is an integer from 1 to 10; and
* indicates a point of attachment.
2. The compound of claim 1 , wherein R f is —CF 3 .
3. The compound of claim 1 , wherein R f is —C 2 F 5 .
4. The compound of claim 1 , wherein R f is —CF 2 CFXCF 3 and X is —F.
5. The compound of claim 1 , wherein R f is —CF 2 CFXCF 3 and X is —OC 3 F 7 .
6. The compound of claim 1 , wherein Z is a single bond, —(CH 2 ) n O—, —OCH 2 CH 2 ) m O—, or —(CH 2 ) n (OCH 2 CH 2 ) m O—.
7. The compound of claim 1 , wherein Y is H.
8. The compound of claim 1 , wherein Y is Cl.
9. The compound of claim 1 wherein Y is Br.
10. The compound of claim 1 , wherein R x , R y , and R z are H.
11. A method for producing compounds of Formula (I)
wherein
R f is —CF 3 , —C 2 F 5 , or —CF 2 CFXCF 3 ;
X is —F, or —OC 3 F 7 ;
Y is —H, —Cl, or —Br;
each R is independently, —H, or C 1 to C 10 alkyl;
R v is —H, or C 1 to C 10 alkyl;
R w is —H, or C 1 to C 10 alkyl;
R x is —H, or C 1 to C 10 alkyl;
R y is —H, or C 1 to C 10 alkyl;
R 1 is —H, or C 1 to C 10 alkyl;
Z is selected from the group consisting of
wherein each R is independently selected from —H or a C 1 to C 10 alkyl;
a is an integer from 1 to 5;
b is an integer from 1 to 5;
c is 0 or 1;
d is an integer from 1 to 10;
m is an integer from 1 to 10;
n is an integer from 1 to 10; and
* indicates a point of attachment;
comprising contacting a compound of Formula (XXI)
wherein
R 1 is —OH, —(CR 2 ) n OH, —(OCR 2 CR 2 ) m OH, —(CR 2 ) n (OCR 2 CR 2 ) m OH, —(OCR 2 CR 2 ) m (CR 2 ) n OH
each R is independently, —H, or C 1 to C 10 alkyl;
a is an integer from 1 to 5;
b is an integer from 1 to 5;
m is an integer from 1 to 10;
n is an integer from 1 to 10
with one or more compounds of formula (XVI)
wherein
R f is —CF 3 , —C 2 F 5 , or —CF 2 CFXCF 3 ; and
X is —F, or —OC 3 F 7 ;
in the presence of a base and a solvent having a donatable Y group wherein Y is H, Cl or Br, and
then contacting the resulting product with epichlorohydrin (or substituted epichlorohydrin of formula (XXI)
wherein
R y is —H, or C 1 to C 10 alkyl;
R w is —H, or C 1 to C 10 alkyl;
R x is —H, or C 1 to C 10 alkyl;
R y is —H, or C 1 to C 10 alkyl;
R z is —H, or C 1 to C 10 alkyl; and
d is an integer from 1 to 10
in the presence of an aqueous base in aqueous solution and a catalyst.
12. The method of claim 11 , wherein the solvent is tetrahydrofuran, carbon tetrachloride, or carbon tetrabromide.
13. The method of claim 12 , wherein the solvent is tetrahydrofuran.
14. The method of claim 11 , wherein the base is potassium carbonate, sodium carbonate, or potassium bicarbonate.
15. The method of claim 14 , wherein the base is potassium carbonate.