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US3956247A Expired / Lapsed US ⏱️ 0.0 years remaining

Halogenation of EPDM in solution in the presence of epoxide and, optionally, poly(alkylene ether) glycol

Assignee: Uniroyal Chemical Co Inc
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Filing: 1975-01-15
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Granted: 1976-05-11
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Expires: 1995-01-15
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Abstract

Abstract Solution halogenation of EPDM (rubbery terpolymer of ethylene, an alpha mono-olefin, and a nonconjugated diene) in the presence of an epoxy compound such as epoxidized soybean oil with or without a poly(alkylene ether) glycol yields a halogenated EPDM of excellent viscosity stability and limited gel content.

Inventors

  • 👤 Vincent Russell Landi
  • 👤 Eliot K. Easterbrook

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-29 13:18
CPC Classifications
C; C08; C08F; C08F8/00; C08F8/18; C08F8/20; C08F8/22

Claims Analysis

Total Claims: 34
Claim 1
Independent Claim 101 words
A method of halogenating an elastomeric, unsaturated, vulcanizable terpolymer of ethylene, an alpha-monoolefin having 3 to 8 carbon atoms and a copolymerizable non-conjugated diene, comprising providing a solution of said terpolymer in an inert organic solvent, adding to said solution a halogen selected from the group consisting of chlorine, bromine, iodine and their interhalogen compounds, and an epoxide, subjecting the solution to a temperature within the range of from -30 to 100°C, whereby the said terpolymer becomes halogenated in the presence of said epoxide, and thereafter recovering from the solution a halogenated terpolymer characterized by viscosity stability and low gel content.
Claim 2
Independent Claim 101 words
A method of halogenating an elastomeric, unsaturated, vulcanizable terpolymer of ethylene, an alpha-monoolefin having 3 to 8 carbon atoms and a copolymerizable non-conjugated diene, comprising providing a solution of said terpolymer in an inert organic solvent, adding to said solution a halogen selected from the group consisting of chlorine, bromine, iodine and their interhalogen compounds, and an epoxide, subjecting the solution to a temperature within the range of from -30 to 100°C, whereby the said terpolymer becomes halogenated in the presence of said epoxide, and thereafter recovering from the solution a halogenated terpolymer characterized by viscosity stability and low gel content.
Claim 3
Dependent Claim 20 words
A method as in claim 1 in which a poly(alkylene ether) glycol is present in the solution during the halogenation.
Claim 4
Dependent Claim 15 words
A method as in claim 2 in which the poly(alkylene ether) glycol is polypropylene glycol.
Claim 5
Dependent Claim 15 words
A method as in claim 1 in which the terpolymer is an ethylene-propylene-non-conjugated diene terpolymer.
Claim 6
Dependent Claim 13 words
A method as in claim 4 in which the non-conjugated diene is 5-ethylidene-2-norbornene.
Claim 7
Dependent Claim 16 words
A method as in claim 1 in which the halogen is bromine, chlorine, or bromine chloride.
Claim 8
Dependent Claim 12 words
A method as in claim 6 in which the halogen is bromine.
Claim 9
Dependent Claim 13 words
A method as in claim 6 in which the halogen is bromine chloride.
Claim 10
Dependent Claim 12 words
A method as in claim 6 in which the halogen is chlorine.
Claim 11
Dependent Claim 21 words
A method as in claim 1 in which the epoxide is epoxidized soybean oil, vinylcyclohexene dioxide, methyl 10,11-epoxyundecanoate, or propylene oxide.
Claim 12
Dependent Claim 14 words
A method as in claim 10 in which the epoxide is epoxidized soybean oil.
Claim 13
Dependent Claim 13 words
A method as in claim 10 in which the epoxide is vinylcyclohexene dioxide.
Claim 14
Dependent Claim 13 words
A method as in claim 10 in which the epoxide is methyl 10,11-epoxyundecanoate.
Claim 15
Dependent Claim 13 words
A method as in claim 10 in which the epoxide is propylene oxide.
Claim 16
Dependent Claim 27 words
A method as in claim 1 in which calcium stearate is added to the solution subsequent to the halogenation and prior to the recovery of the terpolymer.
Claim 17
Independent Claim 190 words
A method of halogenating an elastomeric, unsaturated, vulcanizable terpolymer of ethylene, an alpha-monoolefin having 3 to 8 carbon atoms and a copolymerizable non-conjugated diene, comprising providing a solution in an inert organic solvent containing from 3 to 15% by weight of said terpolymer, adding to said solution from 1 to 10 parts by weight of halogen per 100 parts by weight of said terpolymer, said halogen being selected from the group consisting of chlorine, bromine, iodine and their interhalogen compounds, and an epoxide selected from the group consisting of epoxidized soybean oil, epoxidized higher fatty acid ester, epoxide of a diolefin polymer, bisphenol A-epichlorohydrin reaction product, and epoxide of a monomeric olefinically unsaturated hydrocarbon in amount sufficient to provide from 0.05 to 2 moles of epoxide group per gram atom of halogen present, subjecting the resulting solution to a temperature of from 20° to 80°C. in the absence or near absence of light, whereby the said terpolymer becomes halogenated in the presence of said epoxide, and thereafter recovering from the solution a halogenated terpolymer containing from 0.25% to 10% halogen by weight, characterized by viscosity stability and low gel content.
Claim 18
Independent Claim 190 words
A method of halogenating an elastomeric, unsaturated, vulcanizable terpolymer of ethylene, an alpha-monoolefin having 3 to 8 carbon atoms and a copolymerizable non-conjugated diene, comprising providing a solution in an inert organic solvent containing from 3 to 15% by weight of said terpolymer, adding to said solution from 1 to 10 parts by weight of halogen per 100 parts by weight of said terpolymer, said halogen being selected from the group consisting of chlorine, bromine, iodine and their interhalogen compounds, and an epoxide selected from the group consisting of epoxidized soybean oil, epoxidized higher fatty acid ester, epoxide of a diolefin polymer, bisphenol A-epichlorohydrin reaction product, and epoxide of a monomeric olefinically unsaturated hydrocarbon in amount sufficient to provide from 0.05 to 2 moles of epoxide group per gram atom of halogen present, subjecting the resulting solution to a temperature of from 20° to 80°C. in the absence or near absence of light, whereby the said terpolymer becomes halogenated in the presence of said epoxide, and thereafter recovering from the solution a halogenated terpolymer containing from 0.25% to 10% halogen by weight, characterized by viscosity stability and low gel content.
Claim 19
Dependent Claim 46 words
A method as in claim 16 in which there is further added to the said solution, prior to the halogenation, up to 5% by weight, based on the weight of the terpolymer, of a poly(alkylene ether) glycol having a molecular weight of from 200 to 10,000.
Claim 20
Dependent Claim 29 words
A method as in claim 17 in which the amount of poly(alkylene ether) glycol employed is from 0.25 to 2.5 parts, per 100 parts by weight of the terpolymer.
Claim 21
Dependent Claim 16 words
A method as in claim 18 in which the said poly(alkylene ether) glycol is polypropylene glycol.
Claim 22
Dependent Claim 15 words
A method as in claim 16 in which the terpolymer is an ethylene-propylene-non-conjugated diene terpolymer.
Claim 23
Dependent Claim 13 words
A method as in claim 20 in which the non-conjugated diene is 5-ethylidene-2-norbornene.
Claim 24
Dependent Claim 16 words
A method as in claim 16 in which the halogen is bromine, chlorine, or bromine chloride.
Claim 25
Dependent Claim 12 words
A method as in claim 22 in which the halogen is bromine.
Claim 26
Dependent Claim 13 words
A method as in claim 22 in which the halogen is bromine chloride.
Claim 27
Dependent Claim 12 words
A method as in claim 22 in which the halogen is chlorine.
Claim 28
Dependent Claim 21 words
A method as in claim 16 in which the epoxide is epoxidized soybean oil, vinylcyclohexene dioxide, methyl 10,11-epoxyundecanoate, or propylene oxide.
Claim 29
Dependent Claim 14 words
A method as in claim 26 in which the epoxide is epoxidized soybean oil.
Claim 30
Dependent Claim 13 words
A method as in claim 26 in which the epoxide is vinylcyclohexene dioxide.
Claim 31
Dependent Claim 13 words
A method as in claim 26 in which the epoxide is methyl 10,11-epoxyundecanoate.
Claim 32
Dependent Claim 13 words
A method as in claim 26 in which the epoxide is propylene oxide.
Claim 33
Dependent Claim 8 words
The product of the method of claim 1.
Claim 34
Dependent Claim 8 words
The product of the method of claim 16.

References Cited (Backward Citations)

GB917100A Cited
US3524826A Cited
US3753960A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1979-05-11 1979-11-10 1980-05-11 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1983-05-11 1983-11-10 1984-05-11 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1987-05-11 1987-11-10 1988-05-11 $7700.00 Window Closed / Lapsed

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