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US 12,122,875 B2Granted
Method of making mixture of polymers
AssigneeSolvay Specialty Polymers Italy S.P.A.
InventorsGiovanni Fontana, Marco Galimberti, Vito Tortelli
Life of this patent
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Abstract
The present invention relates to a process for the synthesis of partially and fully fluorinated polyether (PFPE) polymers, 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.
Claims15
A polymer mixture (FHCH2F) comprising variable amounts of any of compounds of formula:
- (a)
- F—CRH1RH2-EH-CRH1RH2—O—[CF2—Rf—CF2O—CRH1RH2-EH-CRH1RH2—O]n*—CF2—Rf—CF2O—CRH1RH2-EH-CRH1RH2—F [formula (FHCH2F-CH2F)];
- (b)
- F—CRH1RH2-EH-CRH1RH2—O—[CF2—Rf—CF2O—CRH1RH2-EH-CRH1RH2—O]n**—CF2—Rf—C(O)—F [formula (FHCOF-CH2F)];
- (c)
- F—C(O)—OCRH1RH2-EH-CRH1RH2—O—[CF2—Rf—CF2O—CRH1RH2-EH-CRH1RH2—O]n′—C(O)—F [formula (FHFOR-FOR)];
- (d)
- F—CRH1RH2-EH-CRH1RH2—O—[CF2—Rf—CF2O—CRH1RH2-EH-CRH1RH2—O]n′—C(O)—F [formula (FHCH2F-FOR)];
- (e)
- F—C(O)—OCRH1RH2-EH-CRH1RH2—O—[CF2—Rf—CF2O—CRH1RH2-EH-CRH1RH2—O]n″—CF2—Rf—C(O)—F [formula (FHCOF-FOR)]
- (f)
- F—C(O)Rf—CF2OCRH1RH2-EH-CRH1RH2—O—[CF2—Rf—CF2O—CRH1RH2-EH-CRH1RH2—O]n′″—CF2—Rf—C(O)—F [formula (FHCOF-COF)]
- wherein:
- n*, n**, n′, n″, and n′″ are integers such that the molecular weight as measured by NMR analysis of the polymer mixture (FHCH2F) is from 210 to 50 000;
- wherein the polymer mixture (FHCH2F) is synthesized from at least:
- at least one perfluoro compound,
- wherein the compound (F) is a compound of the formula:
- F—C(═O)—Rf—C(═O)—F
- wherein Rf is a divalent, perfluoro linear or branched (oxy)alkylene chain, wherein said alkylene chain comprises from 1 to 10 carbon atoms and is optionally interrupted by one or more oxygen atoms;
- and wherein compound (F) is selected from the group consisting of:
- (F-i) FC(O)—CF2—C(O)F;
- (F-ii) FC(O)—CF2—CF2—C(O)F;
- (F-iii) FC(O)—CF2—CF2—CF2—C(O)F;
- (F-iv) FC(O)—CF2—CF2—CF2—CF2—C(O)F;
- and
- (F-v) FC(O)—CF2—O—CF2—C(O)F;
- and
- at least one hydrogenated compound,
- wherein the polymer mixture (FHCH2F) comprises a partially fluorinated polyether backbone having two chain ends, wherein said 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), wherein
- EH 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;
- each of RH1 and RH2, equal to or different from each other at each occurrence, is independently H or a C1-C6 hydrocarbon group;
- and
- wherein in polymer mixture (FHCH2F):
- the concentration of compound of formula (FHCH2F-CH2F), is higher than the concentration of compound of formula (FHFOR-FOR);
- and/or
- the concentration of compound of formula (FHCOF-CH2F), is higher than the concentration of compound of formula (FHCOF-FOR).
33 more elements
A polymer mixture (FFCF3) comprising variable amounts of any of compounds of formula:
- (a″)
- F—CRF1RF2-EF-CRF1RF2—O—[CF2—Rf—CF2O—CRF1RF2-EF-CRF1RF2—O]n*—CF2—Rf—CF2O—CRF1RF2-EF-CRF1RF2—F [formula (FFCF3-CF3)];
- (b″)
- F—CRF1RF2-EF-CRF1RF2—O—[CF2—Rf—CF2O—CRF1RF2-EF-CRF1RF2—O]n**—CF2—Rf—C(O)—F [formula (FFCOF-CF3)];
- (c″)
- F—C(O)—OCRF1RF2-EF-CRF1RF2—O—[CF2—Rf—CF2O—CRF1RF2-EF-CRF1RF2—O]n′—C(O)—F [formula (FFFOR-FOR)];
- (d″)
- F—CRF1RF2-EF-CRF1RF2—O—[CF2—Rf—CF2O—CRF1RF2-EF-CRF1RF2—O]n′—C(O)—F [formula (FFCF3-FOR)];
- (e″)
- F—C(O)—OCRF1RF2-EF-CRF1RF2—O—[CF2—Rf—CF2O—CRF1RF2-EF-CRF1RF2—O]n″—CF2—Rf—C(O)—F [formula (FFCOF-FOR)]
- (f″)
- F—C(O)Rf—CF2—O—CRF1RF2-EF-CRF1RF2—O—[CF2—Rf—CF2O—CRF1RF2-EF-CRF1RF2—O]n″—CF2—Rf—C(O)—F [formula (FFCOF-COF)];
- and optionally further comprising one or more of the following compounds:
- (b″decarb)
- F—CRF1RF2-EF-CRF1RF2—O—[CF2—Rf—CF2O—CRF1RF2-EF-CRF1RF2—O]n**—CF2—Rf—F [formula (FFF-CF3)];
- (e″decarb)
- F—C(O)—OCRF1RF2-EF-CRF1RF2—O—[CF2—Rf—CF2O—CRF1RF2-EF-CRF1RF2—O]n″—CF2—Rf—F [formula (FFF-FOR)]
- (f″decarb)
- F—Rf—CF2—O—CRF1RF2-EF-CRF1RF2—O—[CF2—Rf—CF2O—CRF1RF2-EF-CRF1RF2—O]n′″—CF2—Rf—F [formula (FFF-F)],
- wherein:
- n*, n**, n′, n″, and n′″ are integers such that the molecular weight as measured by NMR analysis of the polymer mixture (FFCF3) is of from 210 to 50 000, —Rf is a divalent, perfluoro linear or branched (oxy)alkylene chain, wherein said alkylene chain comprises from 1 to 10 carbon atoms and is optionally interrupted by one or more oxygen atoms;
- EF is selected from a bond, a —O— group and a divalent linear or branched perfluoro(oxy)alkylene group, wherein said perfluoro(oxy)alkylene group comprises from 1 to 8 carbon atoms and is optionally interrupted by one or more than one ethereal oxygen atom, and
- each of RF1 and RF2, equal to or different from each other, is independently F or a C1-C6 fluorocarbon group;
- and
- wherein in polymer mixture (FFCF3):
- the concentration of compound of formula (FFCF3-CF3) is higher than the concentration of compound of formula (FFFOR-FOR);
- and/or
- the concentration of compound of formula (FFCOF-CF3) is higher than the concentration of compound of formula (FFCOF-FOR).
25 more elements
Dependencies are inferred from the claim text.