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US 11,427,680 B2Granted
(Per)fluoropolyether polymers
AssigneeSolvay Specialty Polymers Italy S.P.A.
InventorsCristiano Monzani, Vito Tortelli, Marco Galimberti, Roberto Valsecchi, Patrizia Maccone
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Abstract
The present invention relates to a novel process for the synthesis of (per)fluoropolyether polymers, to certain novel (per)fluoropolyether polymers. The present invention also relates to the use of the (per)fluoropolyether polymers thus obtained as intermediate compounds for the manufacture of further polymers suitable for use as lubricants, notably for magnetic recording media (MRM).
Claims17
A process (PFH) for the synthesis of at least one polymer (FH), said polymer (FH) comprising a partially fluorinated polyether backbone having two chain ends, wherein said chain ends comprise at least one group selected from hydroxy group, allyl group and vinyl group, said process (PFH) comprising:
- (I) contacting at least one compound (F), wherein compound (F) is a perfluoro compound comprising at least two unsaturated groups selected from vinyl groups and allyl groups, with at least one compound (H), wherein compound (H) is a fully or partially hydrogenated compound comprising at least two hydroxy groups,
- to provide a polymer (FH),
- said polymer (FH) being characterized in that its backbone comprises recurring unit(s) derived from said at least one compound (F) alternately arranged with recurring unit(s) derived from said at least one compound (H).
A polymer (FH*) comprising a partially fluorinated polyether backbone having two chain ends, wherein
- each of said chain ends comprises a group selected from hydroxy group, allyl group or vinyl group;
- and
- said backbone complies with structure (RFH-I):
- —[CF2CFH(CF2)zORCFO(CF2)z*CFHCF2—ORHO]y— (RFH-I)
- wherein
- each of z and z* is independently 0 or 1;
- RCF is a perfluoro alkylene chain comprising from 1 to 20 carbon atoms and optionally interrupted by one or more oxygen atoms;
- RH is a linear or branched alkylene chain comprising from 2 to 12 carbon atoms, said alkyl chain optionally comprising one or more fluorine atoms and optionally being interrupted by one or more oxygen atoms;
- and
- y is an integer, such that the average number molecular weight of the backbone of said polymer (FH) as determined by NMR analysis is from 306 to 50000.
7 more elements
A process (PPFPE) for the synthesis of a polymer (PFPE), said polymer (PFPE) comprising a perfluorinated polyether backbone having two chain ends, wherein each chain end comprises at least one group selected from
- —OC(═O)F and perfluorinated alkyl chain comprising from 2 to 3 carbon atoms, said process (PPFPE) comprising:
- (III) contacting at least one polymer (FH) or polymer (FH*) with a source of fluorine, to provide polymer (PFPE), wherein:
- polymer (FH) is a polymer comprising a partially fluorinated polyether backbone having two chain ends, wherein
- each of said chain ends comprise at least one group selected from hydroxy group, allyl group and vinyl group;
- and
- said backbone comprises recurring unit(s) derived from at least one compound (F), wherein compound (F) is a perfluoro compound comprising at least two unsaturated groups selected from vinyl groups and allyl groups, alternately arranged with recurring unit(s) derived from at least one compound (H), wherein compound (H) is a fully or partially hydrogenated compound comprising at least two hydroxy groups;
- and
- polymer (FH*) is a polymer comprising a partially fluorinated polyether backbone having two chain ends, wherein
- each of said chain ends comprises a group selected from hydroxy group, allyl group or vinyl group;
- and
- said backbone complies with structure (RFH-I):
- —[CF2CFH(CF2)zORCFO(CF2)z*CFHCF2—ORHO]y— (RFH-I)
- wherein
- each of z and z* is independently 0 or 1;
- RCF is a perfluoro alkylene chain comprising from 1 to 20 carbon atoms and optionally interrupted by one or more oxygen atoms;
- RH is a linear or branched alkylene chain comprising from 2 to 12 carbon atoms, said alkyl chain optionally comprising one or more fluorine atoms and optionally being interrupted by one or more oxygen atoms;
- and
- y is an integer, such that the average number molecular weight of the backbone of said polymer (FH) as determined by NMR analysis is from 306 to 50000.
15 more elements
A perfluoropolyether polymer (PFPE), said polymer (PFPE) comprising a perfluoropolyether backbone having two chain ends,
- wherein:
- each chain end comprises at least one group selected from —OC(═O)F and perfluorinated alkyl chain comprising from 2 to 3 carbon atoms and
- said backbone complies with structure (Rpf-I):
- —[CF2CF2(CF2)zORCFO—(CF2)z*CF2CF2—ORFO]y— (Rpf-I)
- wherein
- RCF is a perfluoro alkyl chain comprising from 1 to 20 optionally interrupted by one or more oxygen atoms;
- RF is a perfluoro alkyl chain comprising from 2 to 12 carbon atoms, optionally interrupted by one or more oxygen atoms;
- each of z and z* is independently 0 or 1;
- and
- y is an integer, such that the average number molecular weight of the backbone of said polymer (PFPE) as determined by NMR analysis is from 414 to 70 000;
- with the proviso that:
- when both z and z* are 0, at least one of said moiety RCF and said moiety RF is different from —CF2CF2— and —CF2CF2CF2CF2—;
- and
- when both z and z* are 1, at least one of moiety RCF and moiety RF is different from —CF2CF2CF2—.
11 more elements
A process (PPFPE-EST) for the synthesis of a polymer (PFPEEST), said polymer (PFPEEST) comprising a perfluorinated polyether backbone complying with formula (Rpf-I):
- —[CF2CF2(CF2)zORCFO—(CF2)z*CF2CF2—ORFO]y— (Rpf-I)
- wherein
- RCF is a perfluoro alkyl chain comprising from 1 to 20 optionally interrupted by one or more oxygen atoms;
- RF is a perfluoro alkyl chain comprising from 2 to 12 carbon atoms, optionally interrupted by one or more oxygen atoms;
- each of z and z* is independently 0 or 1;
- and
- y is an integer, such that the average number molecular weight of the backbone of said polymer (PFPE) as determined by NMR analysis is from 414 to 70 000,
- and having two chain ends, wherein at least one chain end comprises at least one group of formula —C(═O)O—Ralk, wherein Ralk is a linear or branched alkyl chain comprising from 1 to 10 carbon atoms, said process (PPFPE-EST) comprising:
- (II) contacting said at least one polymer (FH) or polymer (FH*) , with at least one compound selected from F2C(═O), ClFC(═O), or BrFC(═O);
- (III) contacting the at least one polymer obtained after step (II) with a source of fluorine, to provide polymer (PFPE);
- and
- (IV) contacting the at least one polymer obtained in step (III) with at least one compound of formula Ralk—OH, wherein Ralk is a linear or branched alkyl chain comprising from 1 to 10 carbon atoms, to provide polymer (PFPEEST), wherein:
- polymer (FH) is a polymer comprising a partially fluorinated polyether backbone having two chain ends, wherein
- each of said chain ends comprise at least one group selected from hydroxy group, allyl group and vinyl group;
- and
- said backbone comprises recurring unit(s) derived from at least one compound (F), wherein compound (F) is a perfluoro compound comprising at least two unsaturated groups selected from vinyl groups and allyl groups, alternately arranged with recurring unit(s) derived from at least one compound (H), wherein compound (H) is a fully or partially hydrogenated compound comprising at least two hydroxy groups;
- and
- polymer (FH*) is a polymer comprising a partially fluorinated polyether backbone having two chain ends, wherein
- each of said chain ends comprises a group selected from hydroxy group, allyl group or vinyl group;
- and
- said backbone complies with structure (RFH-I):
- —[CF2CFH(CF2)zORCFO(CF2)z*CFHCF2—ORHO]y— (RFH-I)
- wherein
- each of z and z* is independently 0 or 1;
- RCF is a perfluoro alkylene chain comprising from 1 to 20 carbon atoms and optionally interrupted by one or more oxygen atoms;
- RH is a linear or branched alkylene chain comprising from 2 to 12 carbon atoms, said alkyl chain optionally comprising one or more fluorine atoms and optionally being interrupted by one or more oxygen atoms;
- and
- y is an integer, such that the average number molecular weight of the backbone of said polymer (FH) as determined by NMR analysis is from 306 to 50000.
25 more elements
A polymer (PFPEEST) comprising a perfluoropolyether backbone complying with formula (Rpf-I):
- —[CF2CF2(CF2)zoRCFo—(CF2)z*CF2CF2—ORFO]y— (Rpf-I)
- wherein
- RCF is a perfluoro alkyl chain comprising from 1 to 20 optionally interrupted by one or more oxygen atoms;
- RF is a perfluoro alkyl chain comprising from 2 to 12 carbon atoms, optionally interrupted by one or more oxygen atoms;
- each of z and z* is independently 0 or 1;
- and
- y is an integer, such that the average number molecular weight of the backbone of
- said polymer (PFPE) as determined by NMR analysis is from 414 to 70 000,
- and having two chain ends, wherein at least one chain end, and preferably both said chain comprises at least one group —C(═O)O—Ralk, wherein Ralk is a linear or branched alkyl chain comprising from 1 to 10 carbon atoms.
6 more elements
A polymer (PFPEOH) comprising a perfluoropolyether backbone complying with formula (Rpf-I):
- —[CF2CF2(CF2)zORCFO—(CF2)z*CF2CF2—ORFO]y— (Rpf-I)
- wherein
- RCF is a perfluoro alkyl chain comprising from 1 to 20 optionally interrupted by one or more oxygen atoms;
- RF is a perfluoro alkyl chain comprising from 2 to 12 carbon atoms, optionally interrupted by one or more oxygen atoms;
- each of z and z* is independently 0 or 1;
- and
- y is an integer, such that the average number molecular weight of the backbone of
- said polymer (PFPE) as determined by NMR analysis is from 414 to 70 000,
- and having two chain ends, wherein at least one chain end comprises a group of formula —CF2CH2OH,
- with the proviso that the backbone of said polymer (PFPEOH) is different from —[(C2F4O)a(C4F8O)b]y— wherein each of a, b and y is an integer higher than 1.
7 more elements
A polymer (PFPEOH-X) comprising a perfluoropolyether backbone complying with formula (Rpf-I):
- —[CF2CF2(CF2)zORCFO—(CF2)z*CF2CF2—ORFO]y— (Rpf-I)
- wherein
- RCF is a perfluoro alkyl chain comprising from 1 to 20 optionally interrupted by one or more oxygen atoms;
- RF is a perfluoro alkyl chain comprising from 2 to 12 carbon atoms, optionally interrupted by one or more oxygen atoms;
- each of z and z* is independently 0 or 1;
- and
- y is an integer, such that the average number molecular weight of the backbone of
- said polymer (PFPE) as determined by NMR analysis is from 414 to 70 000,
- and having two chain ends, wherein at least one chain end comprises a group of formula —CF2CH2O—R1, wherein R1 is a linear or branched alkyl chain comprising from 1 to 16 carbon atoms and substituted with at least 2 groups —OH.
6 more elements
The polymer (PFPEOH-X) according to 14, wherein both said chain ends comprise a group complying with one of the following formulae:
- —CF2CH2O—CH2CH(OH)CH2OH (PFPEOH-X1)
- —CF2CH2O—CH2CH(OH)CH2OCH2CH(OH)CH2OH (PFPEOH-X2).
A polymer (PFPEOH-MD) complying with the following formula
- Ce-B-A-B-Ce
- wherein:
- each Ce is a group of formula —CF2CH2O—R1, wherein R1 is a hydrogen atom, linear or branched alkyl chain comprising from 1 to 16 carbon atoms and substituted with at least 2 groups —OH;
- each B is a group complying with formula (Rpf-I):
- —[CF2CF2(CF2)zORCFO—(CF2)z*CF2CF2—ORFO]y— (Rpf-I)
- wherein
- RCF is a perfluoro alkyl chain comprising from 1 to 20 optionally interrupted by one or more oxygen atoms;
- RF is a perfluoro alkyl chain comprising from 2 to 12 carbon atoms, optionally interrupted by one or more oxygen atoms;
- each of z and z* is independently 0 or 1;
- and
- y is an integer, such that the average number molecular weight of the backbone of said polymer (PFPE) as determined by NMR analysis is from 414 to 70 000;
- and
- A is a divalent alkyl chain comprising from 3 to 20 carbon atoms, said alkyl chain being substituted with at least one —OH group(s) and being optionally substituted with at least one fluorine atom.
10 more elements
A method for lubricating a magnetic recording media (MRM), said method comprising providing a magnetic recording media (MRM) comprising at least one magnetic layer, optionally covered by at least one carbon overcoat, and applying at least one of polymer (PFPEOH), polymer (PFPEOH-X) and/or polymer (PFPEOH-MD) onto said magnetic layer or onto said carbon overcoat, wherein:
- polymer (PFPEOH) is a polymer comprising a perfluoropolyether backbone complying with formula (Rpf-I) and having two chain ends, wherein at least one chain end comprises a group of formula —CF2CH2OH, with the proviso that the backbone of said polymer (PFPEOH) is different from —[(C2F4O)a(C4F8O)b]x— wherein each of a, b and y is an integer higher than 1;
- polymer (PFPEOH-X) is a polymer comprising a perfluoropolyether backbone complying with formula (Rd-I) and having two chain ends, wherein at least one chain end comprises a group of formula —CF2CH2O—R1, wherein R1 is a linear or branched alkyl chain comprising from 1 to 16 carbon atoms and substituted with at least 2 groups —OH;
- and
- polymer (PFPEOH-MD) is a polymer complying with the following formula
- Ce-B-A-B-Ce
- wherein:
- each Ce is a group of formula —CF2CH2O—R1, wherein R1 is a hydrogen atom, linear or branched alkyl chain comprising from 1 to 16 carbon atoms and substituted with at least 2 groups —OH;
- each B is a group complying with formula (Rpf-I);
- and
- A is a divalent alkyl chain comprising from 3 to 20 carbon atoms, said alkyl chain being substituted with at least one —OH group(s) and being optionally substituted with at least one fluorine atom,
- and wherein formula (Rpf-I) is:
- —[CF2CF2(CF2)zORCFO—(CF2)z*CF2CF2—ORFO]y— (Rpf-I)
- wherein
- RCF is a perfluoro alkyl chain comprising from 1 to 20 optionally interrupted by one or more oxygen atoms;
- RF is a perfluoro alkyl chain comprising from 2 to 12 carbon atoms, optionally interrupted by one or more oxygen atoms;
- each of z and z* is independently 0 or 1;
- and
- y is an integer, such that the average number molecular weight of the backbone of said polymer (PFPE) as determined by NMR analysis is from 414 to 70 000.
15 more elements
Dependencies are inferred from the claim text.