US4381387A
Expired / Lapsed
US
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Quaterpolymers of the tetrafluoroethylene/ethylene type
Assignee: Hoechst AG
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Filing: 1981-06-22
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Granted: 1983-04-26
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Expires: 2001-06-22
Abstract
Abstract Quaterpolymers are described which are composed of the following copolymerized monomer units (in mole %): (a) 55 to 30% of tetrafluoroethylene, (b) 60 to 40% of ethylene, (c) 10 to 1.5% of hexafluoropropylene and (d) 2.5 to 0.05% of a vinyl monomer which has "bulky" side chains and which can be, for example, a perfluorinated olefin, a perfluorinated vinyl ether, a perfluoroalkyl-substituted vinyl compound, a vinyl or allyl ether or an allyl or vinyl ester. The tensile strength and, in particular, the elongation at break at elevated temperatures is improved by the incorporation of both hexafluoropropylene and "bulky" vinyl monomers. The quaterpolymers are suitable for the manufacture of extruded articles, monofilaments and wire-coatings.
Inventors
- 👤 Reinhard A. Sulzbach
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 08:26
CPC Classifications
C; C08; C08F; C08F214/00; C08F214/18; C08F214/26; C08F214/265; C08F210/00; C08F210/02; H; H01; H01B; H01B3/00; H01B3/18; H01B3/30; H01B3/44; H01B3/443; H01B3/445; Y; Y10; Y10T; Y10T428/00; Y10T428/31504; Y10T428/3154; Y10T428/31544
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
348 words
A thermoplastic fluorine-containing quaterpolymer having a melting point between 245° and 280° C. measured as the minimum of the melting curve by differential thermal analysis and consisting essentially of copolymerized units, in mole percent, of (a) from 55% to 30% tetrafluoroethylene, (b) from 60% to 40% ethylene, (c) from 10% to 1.5% hexafluoropropylene, and (d) from 2.5% to 0.05% of a vinyl monomer selected from one of the classes consisting of (d 1 ) perfluorinated olefins of the formula CF.sub.2 ═CF--Rf1 wherein RF1 is a perfluoroalkyl group having from 2 to 10 carbon atoms, (d 2 ) perfluorinated vinyl ethers of the formula CF.sub.2 ═CF--O--Rf2 wherein Rf2 is a perfluoroalkyl group having from 2 to 10 carbon atoms, (d 3 ) perfluorinated vinyl ethers of the formula ##STR11## wherein n is an integer from 1 to 4, (d 4 ) perfluorinated vinyl ethers of the formula ##STR12## wherein n is 1 or zero, (d 5 ) perfluoro-2-methylene-4-methyl-1.3-dioxolane, (d 6 ) perfluorinated vinyl ethers of the formula CF.sub.2 ═CF--O--(CF.sub.2).sub.n --COX.sub.1 wherein X 1 is F, OH, OR 1 , or NR 2 R 3 , R 1 is an alkyl group having from 1 to 3 carbon atoms, R 2 and R 3 each are H or identical with R 1 , and n is an integer from 1 to 10, (d 7 ) perfluorinated vinyl ethers of the formula ##STR13## wherein X 2 is COOR 4 , COOH, or CN, R 4 is an alkyl group having from 1 to 4 carbon atoms, and n is an integer from 1 to 4, (d 8 ) perfluoroalkyl-substituted vinyl compounds of the formula CH.sub.2 ═CH--Rf3 wherein Rf3 is a perfluoroalkyl group having from 2 to 10 carbon atoms, (d 9 ) 1.1.1-trifluoro-2-(trifluoromethyl)-4-pentene-2-ol, (d 10 ) allyl-2-hydroxyhexafluoroisopropyl ether, (d 11 ) fluorinated allyl ethers of the formula CH.sub.2 ═CR.sub.5 --CH.sub.2 --O--CF.sub.2 --CFX.sub.3 H wherein X 3 is F, Cl or trifluoromethyl, and R 5 is H or CH 3 and (d 12 ) fluorinated vinyl ethers of the formula CH.sub.2 ═CH--O--CF.sub.2 --CFX.sub.3 H wherein X 3 is F, Cl or trifluoromethyl.
Claim 2
Dependent Claim
348 words
A thermoplastic fluorine-containing quaterpolymer having a melting point between 245° and 280° C. measured as the minimum of the melting curve by differential thermal analysis and consisting essentially of copolymerized units, in mole percent, of (a) from 55% to 30% tetrafluoroethylene, (b) from 60% to 40% ethylene, (c) from 10% to 1.5% hexafluoropropylene, and (d) from 2.5% to 0.05% of a vinyl monomer selected from one of the classes consisting of (d 1 ) perfluorinated olefins of the formula CF.sub.2 ═CF--Rf1 wherein RF1 is a perfluoroalkyl group having from 2 to 10 carbon atoms, (d 2 ) perfluorinated vinyl ethers of the formula CF.sub.2 ═CF--O--Rf2 wherein Rf2 is a perfluoroalkyl group having from 2 to 10 carbon atoms, (d 3 ) perfluorinated vinyl ethers of the formula ##STR11## wherein n is an integer from 1 to 4, (d 4 ) perfluorinated vinyl ethers of the formula ##STR12## wherein n is 1 or zero, (d 5 ) perfluoro-2-methylene-4-methyl-1.3-dioxolane, (d 6 ) perfluorinated vinyl ethers of the formula CF.sub.2 ═CF--O--(CF.sub.2).sub.n --COX.sub.1 wherein X 1 is F, OH, OR 1 , or NR 2 R 3 , R 1 is an alkyl group having from 1 to 3 carbon atoms, R 2 and R 3 each are H or identical with R 1 , and n is an integer from 1 to 10, (d 7 ) perfluorinated vinyl ethers of the formula ##STR13## wherein X 2 is COOR 4 , COOH, or CN, R 4 is an alkyl group having from 1 to 4 carbon atoms, and n is an integer from 1 to 4, (d 8 ) perfluoroalkyl-substituted vinyl compounds of the formula CH.sub.2 ═CH--Rf3 wherein Rf3 is a perfluoroalkyl group having from 2 to 10 carbon atoms, (d 9 ) 1.1.1-trifluoro-2-(trifluoromethyl)-4-pentene-2-ol, (d 10 ) allyl-2-hydroxyhexafluoroisopropyl ether, (d 11 ) fluorinated allyl ethers of the formula CH.sub.2 ═CR.sub.5 --CH.sub.2 --O--CF.sub.2 --CFX.sub.3 H wherein X 3 is F, Cl or trifluoromethyl, and R 5 is H or CH 3 and (d 12 ) fluorinated vinyl ethers of the formula CH.sub.2 ═CH--O--CF.sub.2 --CFX.sub.3 H wherein X 3 is F, Cl or trifluoromethyl.
Claim 3
Dependent Claim
154 words
A thermoplastic fluorine-containing quaterpolymer having a melting point between 245° and 280° C. measured as the minimum of the melting curve by differential thermal analysis and consisting essentially of copolymerized units, in mole percent, of (a) from 55% to 30% tetrafluoroethylene, (b) from 60% to 40% ethylene, (c) from 10% to 1.5% hexafluoropropylene, and (d) from 2.5% to 0.05% of a vinyl monomer selected from one of the classes consisting of (d 1 ) perfluorinated olefins of the formula CF.sub.2 ═CF--Rf1 wherein Rf1 is a perfluoroalkyl group having from 2 to 10 carbon atoms, (d 2 ) perfluorinated vinyl ethers of the formula CF.sub.2 ═CF--O--Rf2 wherein Rf2 is a perfluoroalkyl group having from 2 to 10 carbon atoms, (d 3 ) perfluorinated vinyl ethers of the formula ##STR14## wherein n is an integer from 1 to 4, and (d 4 ) perfluorinated vinyl ethers of the formula ##STR15## wherein n is 1 or zero.
Claim 4
Dependent Claim
154 words
A thermoplastic fluorine-containing quaterpolymer having a melting point between 245° and 280° C. measured as the minimum of the melting curve by differential thermal analysis and consisting essentially of copolymerized units, in mole percent, of (a) from 55% to 30% tetrafluoroethylene, (b) from 60% to 40% ethylene, (c) from 10% to 1.5% hexafluoropropylene, and (d) from 2.5% to 0.05% of a vinyl monomer selected from one of the classes consisting of (d 1 ) perfluorinated olefins of the formula CF.sub.2 ═CF--Rf1 wherein Rf1 is a perfluoroalkyl group having from 2 to 10 carbon atoms, (d 2 ) perfluorinated vinyl ethers of the formula CF.sub.2 ═CF--O--Rf2 wherein Rf2 is a perfluoroalkyl group having from 2 to 10 carbon atoms, (d 3 ) perfluorinated vinyl ethers of the formula ##STR14## wherein n is an integer from 1 to 4, and (d 4 ) perfluorinated vinyl ethers of the formula ##STR15## wherein n is 1 or zero.
Claim 5
Dependent Claim
153 words
A thermoplastic fluorine-containing quaterpolymer having a melting point between 245° and 280° C. measured as the minimum of the melting curve by differential thermal analysis and consisting essentially of copolymerized units, in mole percent, of (a) from 55% to 30% tetrafluoroethylene, (b) from 60% to 40% ethylene, (c) from 10% to 1.5% hexafluoropropylene, and (d) from 2.5 to 0.05% of a vinyl monomer selected from one of the classes consisting of (d 8 ) perfluoroalkyl-substituted vinyl compounds of the formula CH.sub.2 ═CH--Rf3 wherein Rf3 is a perfluoroalkyl group having from 2 to 10 carbon atoms, (d 9 ) 1.1.1-trifluoro-2-(trifluoromethyl)-4-pentene-2-ol, (d 11 ) fluorinated allyl ethers of the formula CH.sub.2 ═CR.sub.5 --CH.sub.2 --O--CF.sub.2 -CFX.sub.3 H wherein X 3 is F, Cl, or trifluoromethyl, and R 5 is H or CH 3 , and (d 12 ) fluorinated vinyl ethers of the formula CH.sub.2 ═CH--O--CF.sub.2 --CFX.sub.3 H wherein X 3 is F, Cl, or trifluoromethyl.
Claim 6
Dependent Claim
153 words
A thermoplastic fluorine-containing quaterpolymer having a melting point between 245° and 280° C. measured as the minimum of the melting curve by differential thermal analysis and consisting essentially of copolymerized units, in mole percent, of (a) from 55% to 30% tetrafluoroethylene, (b) from 60% to 40% ethylene, (c) from 10% to 1.5% hexafluoropropylene, and (d) from 2.5 to 0.05% of a vinyl monomer selected from one of the classes consisting of (d 8 ) perfluoroalkyl-substituted vinyl compounds of the formula CH.sub.2 ═CH--Rf3 wherein Rf3 is a perfluoroalkyl group having from 2 to 10 carbon atoms, (d 9 ) 1.1.1-trifluoro-2-(trifluoromethyl)-4-pentene-2-ol, (d 11 ) fluorinated allyl ethers of the formula CH.sub.2 ═CR.sub.5 --CH.sub.2 --O--CF.sub.2 -CFX.sub.3 H wherein X 3 is F, Cl, or trifluoromethyl, and R 5 is H or CH 3 , and (d 12 ) fluorinated vinyl ethers of the formula CH.sub.2 ═CH--O--CF.sub.2 --CFX.sub.3 H wherein X 3 is F, Cl, or trifluoromethyl.
Claim 7
Dependent Claim
52 words
The quaterpolymer of claim 1 which consists essentially of (a) from 55% to 40% tetrafluoroethylene, (b) from 55% to 45% ethylene, (c) from 8% to 3% hexafluoropropylene, and (d) from 1% to 0.1% of a vinyl monomer selected from one of the classes of from (d 1 ) to (d 12 ).
Claim 8
Dependent Claim
52 words
The quaterpolymer of claim 1 which consists essentially of (a) from 55% to 40% tetrafluoroethylene, (b) from 55% to 45% ethylene, (c) from 5% to 3% hexafluoropropylene, and (d) from 0.8% to 0.2% of a vinyl monomer selected from one of the classes of from (d 1 ) to (d 12 ).
Claim 9
Dependent Claim
34 words
The quaterpolymer of claim 1 in which the vinyl monomer (d) is a perfluorinated olefin of the formula CF 2 ═CF--Rf1 wherein Rf1 is a perfluoroalkyl group having from 2 to 5 carbon atoms.
Claim 10
Dependent Claim
35 words
The quaterpolymer of claim 1 in which the vinyl monomer (d) is a perfluorinated vinyl ether of the formula CF 2 ═CF--O-RF2 wherein Rf2 is a perfluoroalkyl group having from 2 to 4 carbon atoms.
Claim 11
Dependent Claim
28 words
The quaterpolymer of claim 1 in which the vinyl monomer (d) is a perfluorinated ether of the formula ##STR16## wherein n is an integer of 1 or 2.
Claim 12
Dependent Claim
20 words
The quaterpolymer of claim 1 in which the vinyl monomer (d) is a perfluorinated vinyl ether of the formula ##STR17##
Claim 13
Dependent Claim
35 words
The quaterpolymer of claim 1 in which the vinyl monomer (d) is a perfluoroalkyl-substituted vinyl compound of the formula CH 2 ═CH--Rf3 wherein Rf3 is a perfluoroalkyl group having from 2 to 6 carbon atoms.
Claim 14
Dependent Claim
13 words
The quaterpolymer of claim 1 in which the vinyl monomer (d) is 1.1.1-trifluoro-2-(trifluoromethyl)-4-pentene-2-ol.
Claim 15
Dependent Claim
40 words
The quaterpolymer of claim 1 in which the vinyl monomer (d) is an allyl ether of the formula CH.sub.2 ═CR.sub.5 -CH.sub.2 -O-CF.sub.2 -CFX.sub.3 H wherein R 5 =H or CH 3 and X 3 =F, Cl or CF 3 .
Claim 16
Dependent Claim
22 words
The quaterpolymer of claim 1 in which the vinyl monomer (d) is a vinyl ether of the formula CH.sub.2 ═CH--O--CF.sub.2 --CF.sub.2 H.
Claim 17
Dependent Claim
30 words
The quaterpolymer of anyone of claims 1 to 11 having a melt flow index of from 5 to 200 g/min measured at 300° C. under a load of 11 kg.
Claim 18
Dependent Claim
30 words
The quaterpolymer of anyone of claims 1 to 11 having a melt flow index of from 15 to 50 g/min measured at 300° C. under a load of 11 kg.
Claim 19
Dependent Claim
12 words
The quaterpolymer of claim 1 in the form of an extruded article.
Claim 20
Dependent Claim
11 words
The quaterpolymer of claim 1 in the form of a filament.
Claim 21
Dependent Claim
12 words
The quaterpolymer of claim 1 in the form of a wire coating.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1986-04-25 | 1986-10-25 | 1987-04-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-04-25 | 1990-10-25 | 1991-04-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-04-25 | 1994-10-25 | 1995-04-26 | $7700.00 | Window Closed / Lapsed |