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US 12,252,583 B2Granted
Method of making mixture of polymers
AssigneeSolvay Specialty Polymers Italy S.P.A.
InventorsGiovanni Fontana, Marco Galimberti, Vito Tortelli
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Abstract
The present invention relates to a process for the synthesis of partially and fully fluorinated polyether (PFPE) polymers comprising cyclic moieties in the backbone chain, to PFPE polymers obtained therefrom and to the use of said PFPE polymers as intermediate compounds for the manufacture of additives for plastic and glass coating.
Claims7
A method for the synthesis of a mixture of polymers said polymers comprising a partially fluorinated polyether backbone possessing a plurality of recurring units including at least one cyclic group;
- said process comprising:
- Step (I):
- a step of contacting:
- at least one fluorinated compound comprising at least two acyl-fluoride groups;
- and
- at least one hydrogenated compound comprising at least two fluoroformate groups of formula —CRH1RH2—O—C(O)F, wherein each of RH1 and RH2, equal to or different from each other at each occurrence, is independently H or a C1-C6 hydrocarbon group, in the presence of at least one fluoride-containing compound, wherein:
- (i) at least one compound (F) is a compound (FC) of formula:
- F—C(═O)-Ef-Rcf-Ef-C(═O)—F
- wherein:
- each of Ef, equal to or different from each other, is a bond, or a divalent fluorocarbon group, possibly comprising one or more than one heteroatoms selected from Cl, N, O and S;
- Rcf is a divalent fluorocarbon cyclic group, which may be a cycloaliphatic or a cycloaromatic group, which may comprise one or more than one cyclic moiety, and which may comprise one or more than one heteroatom included in the cycle, said heteroatom being selected from N, O and S;
- and/or
- (ii) at least one compound (H) is a compound (HC) of formula:
- F—C(═O)O—CRH1RH2-EHC-RHC-EHC-CRH1-RH2—OC(═O)—F
- wherein:
- each of EHC is selected from a bond, a —O— group and a divalent linear or branched (oxy)alkylene group, wherein said (oxy)alkylene group comprises from 1 to 8 carbon atoms and is optionally interrupted by one or more than one ethereal oxygen atom;
- RHC is divalent hydrocarbon cyclic group, which may be a cycloaliphatic or a cycloaromatic group, which may comprise one or more than one cyclic moiety, and which may comprise one or more than one heteroatom included in the cycle, said heteroatom being selected from N, O and S;
- each of RH1 and RH2, equal to or different from each other at each occurrence, is independently H or a C1-C6 hydrocarbon group;
- to provide a polymer mixture (FHcyclic);
- Step (II):
- heating said polymer (FHcyclic) obtained in Step (I) at a temperature exceeding 120° C., for a duration of at least 4 hours and in the presence of a fluoride-containing compound comprising at least one of (i) a metal fluoride of formula MeFy, with Me being a metal having y valence, y being 1 or 2, selected from the group consisting of NaF, CaF2, AgF, RbF, CsF, KF, and combinations thereof;
- and (ii) an (alkyl)ammonium fluoride of formula NRHN4F, with each of RHN, equal to or different from each other being, independently, a H or an alkyl group,
- so effecting the thermolysis of at least a fraction of the chain ends of polymer (FHcyclic) of formula —CRH1RH2—OC(═O)F to groups —CRH1RH2—F,
- to provide polymer mixture (FHcyclic_CH2F);
- Step (IIIA):
- reacting polymer mixture (FHcyclic_CH2F) under esterification conditions in the presence of an alcohol of formula RhOH, with Rh being a C1-C3 hydrocarbon group;
- to provide for polymer mixture (FHcyclic_CH2F-ester/carbonate), and then
- Step (III):
- fluorinating polymer mixture (FHcyclic_CH2F-ester/carbonate) to provide for corresponding fluorinated polymer mixture (FFcyclic_CF3-ester/carbonate).
26 more elements
Dependencies are inferred from the claim text.