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US3720646A Expired / Lapsed US ⏱️ 0.0 years remaining

Perfluoropolyethers modified with quinone compounds in the polymeric chain and process for their preparation

Assignee: Montedison SpA
•
Filing: 1971-03-02
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Granted: 1973-03-13
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Expires: 1991-03-02
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Abstract

Abstract Modified perfluoropolyethers containing, within the polymeric chain, repeating units derived from a quinone compound, are obtained by reacting a peroxidic oxygen-containing perfluoropolyether with a quinone compound, either at an elevated temperature between about 100* and 350* C or under radiation with ultraviolet light at least a portion of which is in the 200-300 millimicron range, whereby the peroxidic bridges are gradually replaced by the quinone units. The reaction is believed to proceed by a free-radical mechanism. The resulting products may be linear, branched, or cross-linked, depending upon the reaction conditions, ratio of reactants, and nature of the starting materials. The products are essentially unvulcanized rubbers which can be vulcanized by common vulcanizing agents such as diamines.

Inventors

  • 👤 D Sianesi
  • 👤 R Fontanelli
  • 👤 A Grazioli

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-05 09:06
CPC Classifications
C; C08; C08G; C08G65/00; C08G65/002; C08G65/005; C08G65/007; F; F24; F24H; F24H1/00; F24H1/22; F24H1/24; F24H1/30; F24H1/32

Claims Analysis

Total Claims: 13
Claim 1
Independent Claim 260 words
A process for the preparation of a modified perfluoropolyether which comprises reacting (1) a starting perfluoropolyether containing peroxidic oxygen and having the formula: (A - O (CF2O)Q- (CF2-CF2O)R-(O)S-B) A - O- (CF2O)Q-(CF2-CF2O)R-(O)Z-D wherein the recurring units have a random distribution along the polymeric chain; each of A and D are terminal groups selected from the group consisting of -CF3, -COF and -CF2-COF; Q and R are each integers from 1 to 150, Z is an integer from one to 50; the sum (Q+R) is a number between about 11 and 200; the ratio Q/R is a number between about 0.2 and 5; and the ratio Z/(Q+R) is a number between about 0.01 and 0.4; with (2) a quinone compound selected from the group consisting of o- and p-benzoquinone, the partially and completely halogenated o- and p-benzoquinones, the halogenated and unhalogenated o- and p- naphthoquinones, and halogenated and unhalogenated anthraquinone, wherein the halogens are selected from the group consisting of fluorine, chlorine and bromine, said reaction being performed either (i) in the presence of ultraviolet light, at least a portion of the radiations of which have a wavelength between about 200 and 300 millimicrons, at a temperature of about 20* to 30* C., or (ii) at an elevated temperature between about 100* and 350* C., whereby to cause a gradual breaking down of the peroxidic bridges of the perfluoropolyether and the insertion at the peroxidic bridge sites, within the perfluoropolyether macromolecular chains, of 0.1 to 10 percent by weight based on the weight of the modified perfluoropolyether of quinone monomeric units.
Claim 2
Dependent Claim 260 words
A process for the preparation of a modified perfluoropolyether which comprises reacting (1) a starting perfluoropolyether containing peroxidic oxygen and having the formula: (A - O (CF2O)Q- (CF2-CF2O)R-(O)S-B) A - O- (CF2O)Q-(CF2-CF2O)R-(O)Z-D wherein the recurring units have a random distribution along the polymeric chain; each of A and D are terminal groups selected from the group consisting of -CF3, -COF and -CF2-COF; Q and R are each integers from 1 to 150, Z is an integer from one to 50; the sum (Q+R) is a number between about 11 and 200; the ratio Q/R is a number between about 0.2 and 5; and the ratio Z/(Q+R) is a number between about 0.01 and 0.4; with (2) a quinone compound selected from the group consisting of o- and p-benzoquinone, the partially and completely halogenated o- and p-benzoquinones, the halogenated and unhalogenated o- and p- naphthoquinones, and halogenated and unhalogenated anthraquinone, wherein the halogens are selected from the group consisting of fluorine, chlorine and bromine, said reaction being performed either (i) in the presence of ultraviolet light, at least a portion of the radiations of which have a wavelength between about 200 and 300 millimicrons, at a temperature of about 20* to 30* C., or (ii) at an elevated temperature between about 100* and 350* C., whereby to cause a gradual breaking down of the peroxidic bridges of the perfluoropolyether and the insertion at the peroxidic bridge sites, within the perfluoropolyether macromolecular chains, of 0.1 to 10 percent by weight based on the weight of the modified perfluoropolyether of quinone monomeric units.
Claim 3
Dependent Claim 13 words
The process of claim 1 wherein the sum (Q+R) is greater than 50.
Claim 4
Dependent Claim 15 words
The process of claim 1 wherein the ratio Q/R is between about 0.3 and 3.
Claim 5
Dependent Claim 15 words
The process of claim 1 wherein the ratio Z/(Q+R) is between about 0.05 and 0.2.
Claim 6
Dependent Claim 14 words
The process of claim 1 which is performed in the absence of free oxygen.
Claim 7
Dependent Claim 13 words
The process of claim 1 which is performed in the absence of solvent.
Claim 8
Dependent Claim 22 words
The process of claim 1 which is performed in the presence of a fluorinated solvent which is liquid under the reaction conditions.
Claim 9
Dependent Claim 11 words
The process of claim 1 which is performed under elevated pressure.
Claim 10
Dependent Claim 16 words
The process of claim 1 wherein the reaction temperature is between about 150* and 250* C.
Claim 11
Dependent Claim 21 words
The process of claim 1 wherein the quinone compound is selected from the group consisting of p-benzoquinone, tetrafluoro-p-benzoquinone, tetrachloro-p-benzoquinone and tetrabromo-p-benzoquinone.
Claim 12
Dependent Claim 26 words
The process of claim 1 wherein the molar ratio of the quinone compound to the peroxidic oxygen groups in said starting perfluoropolyether is less than 5.
Claim 13
Dependent Claim 21 words
The process of claim 7 wherein the fluorinated solvent is selected from the group consisting of CF2Cl2, C2F3Cl3, hexafluorobenzene and perfluorocyclobutane.

References Cited (Backward Citations)

US3544537A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1976-03-12 1976-09-11 1977-03-13 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1980-03-12 1980-09-11 1981-03-13 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1984-03-12 1984-09-11 1985-03-13 $7700.00 Window Closed / Lapsed

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