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US 11,919,834 B2Granted
Method of making perfluorocyclobutane-containing monomer
AssigneeSolvay Specialty Polymers Italy S.P.A.
InventorsRahul Shingte, Debaki Ghosh, Letanzio Bragante, Manuel Gregori, Stefano Millefanti, Emanuela Antenucci, Joel Pollino
Life of this patent
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Abstract
The invention pertains to a multi-step process for making polyfunctional aromatic compounds comprising two phenyl rings bearing reactive groups susceptible of polycondensation reaction to provide polycondensed polymers, said method using economic raw materials, and possessing high selectivity and overall yield.
Claims13
A method for manufacturing a compound of general formula [formula (I)]:
- wherein each of G and G′, equal to or different from each other, is independently selected from the group consisting of
- halogens selected from F, Cl, Br, I;
- —NRH1RH2, with RH1 and RH2 being independently H or a C1-C6, hydrocarbon group;
- —OH;
- nitrile group of formula —CN and nitro group of formula —NO2;
- —COY, with Y being —X, with X being a halogen selected from F, Cl, Br, I;
- —OH;
- —ORH3, —NRH1RH2, with RH3 being a C1-C12 hydrocarbon group;
- and RH1 and RH2 having the meaning detailed above;
- —SO2Y′, with Y′ being —OH, or being —X′, with X′ being a halogen selected from F, Cl, Br, I;
- -E-Ar—X″, with X″ being hydrogen, —OH, —Xoo, —C(O)X# with X# being —OH, or being —Xoo;
- with Xoo being a halogen selected from F, Cl, Br, I;
- -E- being a divalent bridging group selected from the group consisting of a bond, a C1-C6 carbon-containing bridging group;
- a sulphur-containing bridging group,
- a group of formula
- with Xz being —NH2;
- —NO2;
- —OH, —Xoo, —C(O)X# with X# being —OH, or being —Xoo;
- with Xoo being a halogen selected from F, Cl, Br, I;
- each of n, equal to or different from each other, is an integer of 1 to 3, said method comprising:
- Step (a):
- a step of reacting an anion of formula [formula (II)]:
- wherein G″ is a group G or G′, as described above, or is a precursor thereof, with tetrafluoroethylene at a temperature of at most 115° C. and at a pressure of at least 4 bar, so as to obtain a compound of formula [formula (III)]:
- Step (b):
- a step of dimerizing at least one compound of formula (III) obtained from step (a) by thermal treatment at a temperature exceeding 150° C., so as to obtain a compound of formula [formula (IV)]:
- wherein each of G″ and G′″ is a group G or G′, as described above, or is a precursor thereof, being understood that when G″ and G′″ are a group G or G′ as detailed above, compound of formula (IV) qualifies as a compound of formula (I);
- and
- Step (c):
- optionally, a step of reacting compound of formula (IV) in appropriate conditions to transform precursor groups G″ and G′″ of formula (IV) into groups G and G′ so as to obtain compound of formula (I) above.
26 more elements
Dependencies are inferred from the claim text.