US4146532A
Expired / Lapsed
US
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Fluoroelastomer composition with diazobicycloundecenium
Assignee: Daikin Industries Ltd
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Filing: 1977-04-27
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Granted: 1979-03-27
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Expires: 1997-04-27
Abstract
Abstract A fluoroelastomer composition comprising (a) a fluoroelastomer having stabilized end group derived from an isoparaffin selected from the group consisting of isobutane, isopentane and isohexane, (b) at least one member selected from the group consisting of bivalent metal oxides, bivalent metal hydroxides and mixtures of bivalent metal oxide or metal hydroxide with metal salt of weak acid, (c) an aromatic polyhydroxy compound and (d) a quaternary ammonium compound of 8-alkyl- (or 8-aralkyl-)1,8-diazabicyclo[5.4.0]-7-undecenium, provides a fluoro-rubber having low compression set and excellent elastic properties and has excellent processing and storage properties. The fluoroelastomer can be cured with appropriate induction time and fast cure rate by the use of a specific curing agent system mentioned above.
Inventors
- 👤 Yutaka Kometani
- 👤 Shinichi Nakagawa
- 👤 Takeshi Suzuki
- 👤 Yasuyoshi Furukawa
- 👤 Tsuneo Nakagawa
- 👤 Masayasu Tomoda
- 👤 Masahiko Oka
- 👤 Tutomu Terada
- 👤 Yutaka Ueta
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 21:02
CPC Classifications
C; C08; C08K; C08K5/00; C08K5/16; C08K5/34; C08K5/3442; C08K5/3462; C08K5/3465; C08K13/00; C08K13/02
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
242 words
In a fluoroelastomer composition comprising (a) a fluoroelastomeric copolymer of vinylidene fluoride and at least one other copolymerizable fluorine-containing monomer prepared by copolymerizing vinylidene fluoride and said other copolymerizable fluorine-containing monomer in an aqueous medium in the presence of an inorganic free-radical initiator selected from the group consisting of sodium, potassium or ammonium persulfates, perphosphates, perborates and percarbonates and hydrogen peroxide in the presence of an isoparaffin selected from the group consisting of isobutane, isopentane and isohexane, (b) at least one member selected from the group consisting of bivalent metal oxides, bivalent metal hydroxides and mixtures of a bivalent metal oxide or a bivalent metal hydroxide with a metal salt of a weak acid, (c) an aromatic polyhydroxy compound and (d) a quaternary ammonium compound having the following general formula: ##STR2## wherein R is an alkyl group having from 1 to 24 carbon atoms or an aralkyl group having from 7 to 20 carbon atoms, and X - is an anion selected from the group consisting of a halide ion, hydroxylate ion, alkoxylate ion, carboxylate ion, phenoxide ion, sulfonate ion, sulfate ion, sulfite ion and carbonate ion, the improvement which comprises employing a fluoroelastomer having ionic end groups derived from an inorganic free-radical initiator and nonionic end groups derived from an isoparaffin selected from the group consisting of isobutane, isopentane and isohexane and a ratio of the nonionic end groups to all end groups in the polymer chain of 5 to 85%.
Claim 2
Dependent Claim
242 words
In a fluoroelastomer composition comprising (a) a fluoroelastomeric copolymer of vinylidene fluoride and at least one other copolymerizable fluorine-containing monomer prepared by copolymerizing vinylidene fluoride and said other copolymerizable fluorine-containing monomer in an aqueous medium in the presence of an inorganic free-radical initiator selected from the group consisting of sodium, potassium or ammonium persulfates, perphosphates, perborates and percarbonates and hydrogen peroxide in the presence of an isoparaffin selected from the group consisting of isobutane, isopentane and isohexane, (b) at least one member selected from the group consisting of bivalent metal oxides, bivalent metal hydroxides and mixtures of a bivalent metal oxide or a bivalent metal hydroxide with a metal salt of a weak acid, (c) an aromatic polyhydroxy compound and (d) a quaternary ammonium compound having the following general formula: ##STR2## wherein R is an alkyl group having from 1 to 24 carbon atoms or an aralkyl group having from 7 to 20 carbon atoms, and X - is an anion selected from the group consisting of a halide ion, hydroxylate ion, alkoxylate ion, carboxylate ion, phenoxide ion, sulfonate ion, sulfate ion, sulfite ion and carbonate ion, the improvement which comprises employing a fluoroelastomer having ionic end groups derived from an inorganic free-radical initiator and nonionic end groups derived from an isoparaffin selected from the group consisting of isobutane, isopentane and isohexane and a ratio of the nonionic end groups to all end groups in the polymer chain of 5 to 85%.
Claim 3
Dependent Claim
22 words
The composition of claim 1, wherein said fluoroelastomer having stabilized end groups has an end group stabilization ratio of 5 to 30%.
Claim 4
Dependent Claim
30 words
The composition of claim 1, wherein said quaternary ammonium compound is present in an amount of 0.2 to 10 parts by weight per 100 parts by weight of the fluoroelastomer.
Claim 5
Dependent Claim
30 words
The composition of claim 1, wherein said quaternary ammonium compound is present in an amount of 0.3 to 3 parts by weight per 100 parts by weight of the fluoroelastomer.
Claim 6
Dependent Claim
48 words
The composition of claim 1, wherein said quaternary ammonium compound is a member selected from the group consisting of 8-methyl-1,8-diaza-bicyclo[5.4.0]-7-undecenium chloride, 8-methyl-1,8-diaza-bicyclo[5.4.0]-7-undecenium iodide, 8-methyl-1,8-diaza-bicyclo[5.4.0]-7-undecenium hydroxide, 8-methyl-1,8-diaza-bicyclo[5.4.0]-7-undecenium methylsulfate, 8-ethyl-1,8-diaza-bicyclo[5.4.0]-7-undecenium bromide, 8-propyl-1,8-diaza-bicyclo[5.4.0]-7-undecenium bromide, 8-dodecyl-1,8-diaza-bicyclo[5.4.0]-7-undecenium chloride, 8-dodecyl-1,8-diaza-bicyclo[5.4.0]-7-undecenium hydroxide, 8-eicosyl-1,8-diaza-bicyclo[5.4.0]-7-undecenium chloride, 8-tetracosyl-1,8-diaza-bicyclo[5.4.0.]-7-undecenium chloride, 8-benzyl-1,8-diaza-bicyclo[5.4.0]-7-undecenium chloride, 8-benzyl-1,8-diaza-bicyclo[5.4.0]-7-undecenium hydroxide, 8-phenethyl-1,8-diaza-bicyclo[5.4.0]-7-undecenium chloride and 8-(3-phenylpropyl)-1,8-diaza-bicyclo[5.4.0]-7-undecenium chloride.
Claim 7
Dependent Claim
29 words
The composition of claim 1, wherein said ingredient (b) is present in an amount of 2 to 30 parts by weight per 100 parts by weight of the fluoroelastomer.
Claim 8
Dependent Claim
29 words
The composition of claim 1, wherein said ingredient (b) is present in an amount of 5 to 20 parts by weight per 100 parts by weight of the fluoroelastomer.
Claim 9
Dependent Claim
30 words
The composition of claim 1, wherein said aromatic polyhydroxy compound is present in an amount of 0.5 to 5 parts by weight per 100 parts by weight of the fluoroelastomer.
Claim 10
Dependent Claim
30 words
The composition of claim 1, wherein said aromatic polyhydroxy compound is present in an amount of 1 to 2 parts by weight per 100 parts by weight of the fluoroelastomer.
Claim 11
Dependent Claim
15 words
The composition of claim 1, wherein said aromatic polyhydroxy compound is hydroquinone, 2,2-bis(4-hydroxyphenyl)propane or 2,2-bis(4-hydroxyphenyl)perfluoropropane.
Claim 12
Dependent Claim
17 words
The composition of claim 1, wherein said fluoroelastomer is a terpolymer of vinylidene fluoride, tetrafluoroethylene and hexafluoropropene.
Claim 13
Dependent Claim
24 words
The composition of claim 1, wherein said fluorine-containing monomer is trifluoroethylene, tetrafluoroethylene, trifluorochloroethylene, trifluoropropene, hexafluoropropene, pentafluoropropene, vinyl fluoride or perfluoro methyl perfluoro vinyl ether.
Claim 14
Dependent Claim
16 words
The composition of claim 1, wherein said fluoroelastomer is a copolymer of vinylidene fluoride and hexafluoropropene.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-03-26 | 1982-09-25 | 1983-03-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-03-26 | 1986-09-25 | 1987-03-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-03-26 | 1990-09-25 | 1991-03-27 | $7700.00 | Window Closed / Lapsed |