Process for the manufacture of functional PFPE derivative
A process for the manufacture of a functional (per)fluoropolyether derivative comprising at least one triazole group, such process comprising: (1) reacting a (per)fluoropolyether hydroxyl derivative having at least one hydroxyl group [derivative (PFPE-OH)] with an activating agent, to yield an activated (per)fluoropolyether hydroxyl derivative comprising at least one activated hydroxyl group [derivative (a-PFPE-OH)];(2) reacting said activated (per)fluoropolyether hydroxyl derivative [derivative (a-PFPE-OH)] with at least one azide salt to yield a functional (per)fluoropolyether derivative comprising at least one azido group [derivative (PFPE-N 3 )] ; and (3) reacting said functional (per)fluoropolyether derivative comprising at least one azido group [derivative (PFPE-N 3 )] with a hydrocarbon compound having a terminal alkyne group to yield a functional (per)fluoropolyether derivative comprising at least one triazole group [derivative (PFPE-azole)].
1. A (per)fluoropolyether triazole derivative comprising at least one fluoropolyoxyalkene chain (R f ) and at least one triazole group [derivative (PFPE-azole)], said derivative (PFPE-azole) complying with the following formula:
T Az2 —O—R f —T Az1
wherein:
—R f is a fluoropolyoxyalkene chain comprising repeating units R°, said repeating units being selected from the group consisting of:
(i) —CFXO—, wherein X is F or CF 3 ,
(ii) —CFXCFXO—, wherein X, equal or different at each occurrence, is F or CF 3 , with the provision that at least one of X is —F,
(iii) —CF 2 CF 2 CF 2 O—,
(iv) —CF 2 CF 2 CF 2 CF 2 O—, and
(v) —(CF 2 ) j —CFZ—O—, wherein j is an integer from 0 to 3, and Z is a group of general formula: —OR f 'T 3 , wherein R f ' is a fluoropolyoxyalkene chain comprising a number of repeating units from 0 to 10, said recurring units selected from the group consisting of: —CFXO—, —CF 2 CFXO—, —CF 2 CF 2 CF 2 O—, and —CF 2 CF 2 CF 2 CF 2 O—, with each of X being independently F or CF 3 , and T 3 being a C 1 -C 3 perfluoroalkyl group, and
—T Az1 and T AZ2 , equal to or different from each other, are independently selected from the group consisting of:
non-functional groups free from hydroxyl groups; and
functional triazole groups comprising an azole group of formula:
with R H being a hydrocarbon group, optionally fluorinated, with the proviso that at least one of T Az1 and T Az2 is an azole-containing group.
2. The derivative (PFPE-azole) of claim 1 , complying with the following formula (1):
T Az2 —O—(CFX 1 O ) c1 (CFX 2 CFX 3 O) c2 (CF 2 CF 2 CF 2 O) c3 (CF 2 CF 2 CF 2 CF 2 O) c4 —T Az1 wherein
—X 1 , X 2 , X 3 equal to or different from each other and at each occurrence are independently —F or —CF 3 ;
—T Az1 and T Az2 , equal to or different from each other, have same meaning as defined in claim 1 ;
—c1, c2 , c3, and c4, equal to or different from each other, are independently integers ≧0, such that and cl+c2+c3+c4 is in the range 5 to 2000; with the provision that should at least two of c1, c2, c3 and c4 be different from zero, the different recurring units are statistically distributed along the chain.
3. A method for making a lubricating composition or polymer material, comprising using the derivative (PFPE-azole) of claim 1 as an additive-in a lubricating composition or in a polymer material.
4. The derivative (PFPE-azole) of claim 2 , wherein c1+c2+c3+c4 is between 10 and 500.
5. The derivative (PFPE-azole) of claim 2 , wherein the non-functional groups free from hydroxyl groups are each independently selected from —CF 3 , —CF 2 —CF 3 , —CF 2 Cl, —CF 2 CF 2 Cl, —CF 2 —COF, —COF and mixtures thereof.
6. A lubricating composition or polymer material comprising the derivative (PFPE-azole) of claim 1 .