US3978161A
Expired / Lapsed
US
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Metalation of polymers
Assignee: Aerojet Rocketdyne Holdings Inc
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Filing: 1975-07-29
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Granted: 1976-08-31
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Expires: 1995-07-29
Abstract
Abstract Hydrocarbon polymers are readily metalated in solution in a hydrocarbon solvent with metallic sodium, potassium, rubidium and/or cesium utilizing a chelating polytertiary amine or a crown polyether.
Inventors
- 👤 Stuart D. Nielsen
- 👤 Ivan G. Hargis
- 👤 Russell A. Livigni
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 09:02
CPC Classifications
C; C08; C08F; C08F8/00; C08F8/42; C08C; C08C19/00; C08C19/26
Claims Analysis
Total Claims: 7
Claim 1
Independent Claim
136 words
The method for metalating a hydrocarbon polymer having aliphatic ethylenic unsaturation and having replaceable hydrogen atoms in the polymer chain which comprises reacting said polymer in solution in a liquid hydrocarbon solvent which is essentially free of aliphatic unsaturation and of sodium oxide with metallic sodium in admixture with a hydrocarbon polytertiary amine free of aliphatic unsaturation and having from 2 to 4 tertiary nitrogen atoms as a chelating agent at a temperature of from about 0° to 100°C. and for a time sufficient to effect bonding of said sodium to said polymer by means of a direct carbon to sodium bond, said chelating agent being used in an amount of from about 0.1 to 2.5 moles per gram atom of said sodium and said chelating agent being unreactive with the carbanion formed on said polymer.
Claim 2
Independent Claim
136 words
The method for metalating a hydrocarbon polymer having aliphatic ethylenic unsaturation and having replaceable hydrogen atoms in the polymer chain which comprises reacting said polymer in solution in a liquid hydrocarbon solvent which is essentially free of aliphatic unsaturation and of sodium oxide with metallic sodium in admixture with a hydrocarbon polytertiary amine free of aliphatic unsaturation and having from 2 to 4 tertiary nitrogen atoms as a chelating agent at a temperature of from about 0° to 100°C. and for a time sufficient to effect bonding of said sodium to said polymer by means of a direct carbon to sodium bond, said chelating agent being used in an amount of from about 0.1 to 2.5 moles per gram atom of said sodium and said chelating agent being unreactive with the carbanion formed on said polymer.
Claim 3
Dependent Claim
46 words
The method according to claim 1 in which said amine is selected from the group consisting of tetramethylethylene diamine, sparteine, tetramethyl-1,2-diamino cyclohexane, tris-(2-dimethylaminoethyl) amine, pentamethyl diethylene triamine, hexamethyltriethylene tetramine, triethylene diamine, N,N'-dimethyl piperazine,tetramethyl-1,4-diamino cyclohexane, tetraethylethylene diamine, tetradecylethylene diamine, and tetraoctyl hexylenediamine, and mixtures of the same.
Claim 4
Dependent Claim
36 words
The method according to claim 1 in which said solvent is selected from the group consisting of hexane, heptane, octane, nonane, cyclohexane, cycloheptane, cyclooctane, cyclopentane, decane, dodecane, 2,5-dimethylhexane, 1,3-dimethyl cyclohexane, and isopropyl cyclohexane and mixtures thereof.
Claim 5
Dependent Claim
37 words
The method according to claim 1 where the temperature is from about 40° to 90°C. and said chelating agent is used in an amount of from about 0.2 to 1.5 moles per gram atom of said sodium.
Claim 6
Dependent Claim
24 words
The method according to claim 4 in which said polymer is selected from the group consisting of polybutadiene-1,3 and copolymers of butadiene-1,3 and styrene.
Claim 7
Dependent Claim
14 words
The method according to claim 4 in which said polytertiary amine is tetramethylethylene diamine.
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) | 1979-08-31 | 1980-03-01 | 1980-08-31 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-08-31 | 1984-03-01 | 1984-08-31 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-08-31 | 1988-03-01 | 1988-08-31 | $7700.00 | Window Closed / Lapsed |