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US4184988A
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Process for the sulfonation of an elastomeric polymer
Assignee: ExxonMobil Technology and Engineering Co
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Filing: 1978-10-16
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Granted: 1980-01-22
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Expires: 1998-10-16
Abstract
Abstract An improved process for the sulfonation of an unsaturated elastomeric polymer to form a sulfonated elastomeric polymer, wherein a cement which contains an elastomeric polymer dissolved in a nonreactive solvent is contacted with a sulfonating agent at between about -100 DEG C. and +100 DEG C. for a period of time sufficient to result in sulfonation of the elastomeric polymer wherein the improvement includes the use of a sulfonating agent which is formed from mixtures of acyl sulfate <IMAGE> with carboxylic acid anhydrides <IMAGE> with carboxylic acid halides <IMAGE> or with both, wherein R is selected from the group consisting of CH3-, C2H5-, C3H7-, C4H9-, C5H11, C6H13 or C6H5 and mixtures thereof. The molar ratio of <IMAGE> is at least one.
Inventors
- 👤 Henry S. Makowski
- 👤 Robert D. Lundberg
- 👤 Jan Bock
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 19:59
CPC Classifications
C; C08; C08C; C08C19/00; C08C19/20; C08F; C08F8/00; C08F8/34; C08F8/36; C08F8/44; C08F2800/00; C08F2800/20
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
187 words
A process for sulfonating an unsaturated polymer to form a sulfonated polymer, which comprises the steps of: (a) forming a cement of said unsaturated polymer in a non-reactive solvent; and (b) contacting said cement with a sulfonating agent at a temperature of about -100° C. to about +100° C. for a sufficient period of time to form a sulfonated polymer having about 15 to about 50 meq. of sulfonate groups per 100 grams of said sulfonated polymer, said sulfonating agent being a mixture of RCO 2 SO 3 H and a second reagent which is selected from the group consisting of (RCO) 2 O and RCO X , a molar ratio of said second reagent to said RCO 2 SO 3 H being at least about one, wherein R is selected from the group consisting of CH 3 --, C 2 H 5 --, C 3 H 7 --, C 4 H 9 --, C 5 H 11 --, C 6 H 13 --, and C 6 H 5 CH 2 and mixtures thereof, and X is selected from the group consisting of F, Cl and Br.
Claim 2
Dependent Claim
187 words
A process for sulfonating an unsaturated polymer to form a sulfonated polymer, which comprises the steps of: (a) forming a cement of said unsaturated polymer in a non-reactive solvent; and (b) contacting said cement with a sulfonating agent at a temperature of about -100° C. to about +100° C. for a sufficient period of time to form a sulfonated polymer having about 15 to about 50 meq. of sulfonate groups per 100 grams of said sulfonated polymer, said sulfonating agent being a mixture of RCO 2 SO 3 H and a second reagent which is selected from the group consisting of (RCO) 2 O and RCO X , a molar ratio of said second reagent to said RCO 2 SO 3 H being at least about one, wherein R is selected from the group consisting of CH 3 --, C 2 H 5 --, C 3 H 7 --, C 4 H 9 --, C 5 H 11 --, C 6 H 13 --, and C 6 H 5 CH 2 and mixtures thereof, and X is selected from the group consisting of F, Cl and Br.
Claim 3
Dependent Claim
17 words
The process of claim 1, wherein such sulfonating agent is formed prior to addition to said cement.
Claim 4
Dependent Claim
16 words
The process of claim 1, wherein said sulfonating agent is formed in situ in said cement.
Claim 5
Dependent Claim
26 words
The process of claim 1, wherein such sulfonating agent is formed from a mixture of said (RCO) 2 O and concentrated H 2 SO 4 .
Claim 6
Dependent Claim
26 words
The process of claim 1, wherein said sulfonating agent is formed from a mixture of said (RCO) 2 O, RCOCl and H 2 SO 4 .
Claim 7
Dependent Claim
23 words
The process of claim 1, wherein said sulfonating agent is formed from a mixture of said (RCO) 2 O and ClSO 3 H.
Claim 8
Dependent Claim
22 words
The process of claim 1, wherein such sulfonating agent is formed from a mixture of RCOCl and H 2 SO 4 .
Claim 9
Dependent Claim
18 words
The process according to claim 1, wherein said cement contains at least about 0.1 wt. % of water.
Claim 10
Dependent Claim
12 words
The process according to claim 1, wherein said elastomeric polymer is neoprene.
Claim 11
Dependent Claim
26 words
The process according to claim 1, wherein said elastomeric polymer is selected from the group consisting of Butyl rubbers, styrene-butadiene copolymers, isoprene-styrene copolymers, and EPDM terpolymers.
Claim 12
Dependent Claim
28 words
The process according to claim 1, wherein said sulfonated elastomeric polymer has about 20 to about 40 meq. sulfonate groups per 100 grams of said sulfonated elastomeric polymer.
Claim 13
Dependent Claim
46 words
The process according to claim 1, further including neutralizing at least about 95% of said sulfonate groups with a metal counterion selected from the group consisting of antimony, iron, lead and Groups I-A, II-A, I-B and II-B of the Periodic Table of Elements and mixtures thereof.
Claim 14
Dependent Claim
35 words
The process according to claim 12, further including adding an ionic plasticizer at a concentration level of at least about 3 parts by weight per 100 parts by weight of said neutralized sulfonated elastomeric polymer.
Claim 15
Dependent Claim
39 words
The process according to claim 13 further including an additive to said neutralized sulfonated elastomeric polymer at a concentration level of less than about 300 parts by weight per 100 parts by weight of said neutralized sulfonated elastomeric polymer.
Claim 16
Dependent Claim
28 words
The process according to claim 14, wherein said additive is selected from the group consisting of oils, fillers, waxes, pigments, a metallic hydroxide and stabilizers and mixtures thereof.
Claim 17
Dependent Claim
30 words
The process according to claim 1, wherein said non-reactive solvent is selected from the group consisting of aliphatic hydrocarbons, chlorinated aliphatics, aromatic hydrocarbons, and chlorinated aromatic hydrocarbons and mixtures thereof.
Claim 18
Dependent Claim
52 words
The process of claim 1 wherein at least 70% of the amount of sulfonating agent present in the reaction zone that does not exceed the stoichiometric amount of sulfonating agent required to react with all available sites of unsaturation in said elastomeric polymer is converted to sulfonate groups on said elastomeric polymer.
Claim 19
Dependent Claim
21 words
The process of claim 1, wherein said elastomeric polymer dissolved in such non-reactive solvent contains at least 0.2 wt. % water.
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) | 1983-01-21 | 1983-07-23 | 1984-01-22 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-01-21 | 1987-07-23 | 1988-01-22 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-01-21 | 1991-07-23 | 1992-01-22 | $7700.00 | Window Closed / Lapsed |