US4220739A
Expired / Lapsed
US
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Method for sulfonating organic materials
Assignee: Dow Chemical Co
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Filing: 1978-07-28
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Granted: 1980-09-02
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Expires: 1998-07-28
Abstract
Abstract Organic materials such as polyethylene, polystyrene and polypropylene are more efficiently sulfonated by contacting them with an essentially dry gaseous mixture of sulfur trioxide and chlorine. Sulfonated organic polymers prepared by this process are adhesive, antistatic and highly impermeable to oleophilic materials such as gasoline, and common hydrocarbon solvents.
Inventors
- 👤 Wilhelm E. Walles
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 15:00
CPC Classifications
C; C08; C08F; C08F8/00; C08F8/34; C08F8/36
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
106 words
A process for sulfonating organic compounds which comprises contacting a sulfonatable organic compound which have hydrogen atoms bonded to carbon atoms which are replaceable by sulfonic acid groups with an essentially dry gaseous mixture comprising sulfur trioxide and suitably active halogen selected from the group consisting of fluorine, bromine, chlorine or mixtures thereof which inherently form interhalogen compounds, wherein the amount of sulfur trioxide is sufficient to provide a desired degree of sulfonation and the amount of halogen is sufficient to accelerate the rate of sulfonation at least 10 percent relative to the rate of sulfonation achieved by using sulfur trioxide in the absence of halogen.
Claim 2
Dependent Claim
106 words
A process for sulfonating organic compounds which comprises contacting a sulfonatable organic compound which have hydrogen atoms bonded to carbon atoms which are replaceable by sulfonic acid groups with an essentially dry gaseous mixture comprising sulfur trioxide and suitably active halogen selected from the group consisting of fluorine, bromine, chlorine or mixtures thereof which inherently form interhalogen compounds, wherein the amount of sulfur trioxide is sufficient to provide a desired degree of sulfonation and the amount of halogen is sufficient to accelerate the rate of sulfonation at least 10 percent relative to the rate of sulfonation achieved by using sulfur trioxide in the absence of halogen.
Claim 3
Dependent Claim
24 words
The process of claim 2 wherein the mixture is a gaseous mixture of sulfur trioxide, chlorine and a dry gas inert to the sulfonation.
Claim 4
Dependent Claim
14 words
The process of claim 2 wherein the dry gas is dry air or nitrogen.
Claim 5
Dependent Claim
15 words
The process of claim 3 wherein the organic compound is a normally solid organic polymer.
Claim 6
Dependent Claim
18 words
The process of claim 4 wherein the polymer is a polymer of an α-olefin or a monovinylidene aromatic.
Claim 7
Dependent Claim
10 words
The process of claim 5 wherein the polymer is polyethylene.
Claim 8
Dependent Claim
41 words
The process of claim 6 wherein the amount of sulfur trioxide is from about 0.1 to 50 volume percent of the dry mixture and the amount of halogen is from about 0.1 to about 99 volume percent of the dry mixture.
Claim 9
Dependent Claim
42 words
The process of claim 6 wherein the amount of sulfur trioxide is from about 5 to about 20 volume percent of the dry mixture and the amount of halogen is from about 20 to about 80 volume percent of the dry mixture.
Claim 10
Dependent Claim
14 words
The process of claim 1 wherein the organic compound is a sulfonatable organic polymer.
Claim 11
Dependent Claim
103 words
The process of claim 9 wherein the polymer is an addition homopolymer or copolymer of one or more of the following monomers: aliphatic a-monoolefins, aliphatic conjugated and nonconjugated polyenes including dienes and trienes, halogenated aliphatic olefins, a,b-ethylenically unsaturated carboxylic acids, vinyl esters of nonpolymerizable carboxylic acids, alkyl esters of a,b-ethylenically unsaturated carboxylic acids, monovinylidene aromatic monomers, a,b-ethylenically unsaturated nitriles and other ethylenically unsaturated monomers which polymerize across the ethylenic bond to form polymers having a linear carbon to carbon backbone molecular structure of a plurality of free hydrogen atoms attached to the chain and/or attached to carbon atoms of substituents of the chain.
Claim 12
Dependent Claim
25 words
The process of claim 8 wherein the process is carried out at a sulfonation temperature in the range from about 10° to about 50° C.
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) | 1983-09-02 | 1984-03-03 | 1984-09-02 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-09-02 | 1988-03-03 | 1988-09-02 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-09-02 | 1992-03-03 | 1992-09-02 | $7700.00 | Window Closed / Lapsed |