Patent US4118360A successfully refreshed from Google Patents.
US4118360A
Expired / Lapsed
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Oil extended elastomeric compositions
Assignee: ExxonMobil Technology and Engineering Co
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Filing: 1977-11-29
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Granted: 1978-10-03
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Expires: 1997-11-29
Abstract
Abstract This invention relates to an improved process for the manufacture of a blend composition of a neutralized sulfonated elastomeric polymer which includes the steps of sulfonating an elastomeric polymer dissolved in a solvent to form an acid form of the sulfonated elastomeric polymer. The solution of the acid form of the sulfonated elastomeric polymer is quenched with an oxirane to form a polymeric hydroxyalkyl sulfonate. A non-polar backbone process oil is added thereby plasticizing the polymeric backbone of the hydroxyalkyl sulfonate. The hydroxyalkyl sulfonate is reacted with a metal carboxylate to form equal molar portions of a solid gel-free neutralized sulfonated elastomeric polymer and a hydroxyalkyl carboxylate ester.
Inventors
- 👤 Henry S. Makowski
- 👤 Charles P. O'Farrell
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 21:11
CPC Classifications
C; C08; C08C; C08C19/00; C08C19/30; C08C19/20; C08F; C08F8/00
Claims Analysis
Total Claims: 35
Claim 1
Independent Claim
197 words
A process for the manufacture of a sulfonated elastomeric blend, which comprises the following steps: (a) dissolving an elastomeric polymer in a solvent to form a cement; (b) sulfonating with a sulfonating agent said elastomeric polymer in said cement to form an acid form of a sulfonated elastomeric polymer; (c) reacting said acid form of said sulfonated elastomeric polymer with an oxirane to form a hydroxyalkylated sulfonated polymer, said oxirane having the general formula: ##STR6## wherein R 1 , R 2 , R 3 and R 4 are independently selected from the group consisting essentially of hydrogen and C 1 to C 18 straight and branched chain acyclic, alicyclic, aryl, alkylaryl, arylalkyl radicals and their functional derivatives; (d) recovering said hydroxyalkyl sulfonated polymer from said cement; (e) adding about 5 to about 200 parts per hundred by weight of a non-polar process oil to 100 parts of said hydroxyalkylated sulfonated polymer to form a blend of said oil and said hydroxyalkyl sulfonated polymer; and (f) reacting said blend of said oil and said hydroxyalkyl sulfonated polymer with a metal containing base to form a neutralized sulfonated elastomeric polymer and a hydroxyalkyl carboxylate ester having the formula: ##STR7##
Claim 2
Dependent Claim
197 words
A process for the manufacture of a sulfonated elastomeric blend, which comprises the following steps: (a) dissolving an elastomeric polymer in a solvent to form a cement; (b) sulfonating with a sulfonating agent said elastomeric polymer in said cement to form an acid form of a sulfonated elastomeric polymer; (c) reacting said acid form of said sulfonated elastomeric polymer with an oxirane to form a hydroxyalkylated sulfonated polymer, said oxirane having the general formula: ##STR6## wherein R 1 , R 2 , R 3 and R 4 are independently selected from the group consisting essentially of hydrogen and C 1 to C 18 straight and branched chain acyclic, alicyclic, aryl, alkylaryl, arylalkyl radicals and their functional derivatives; (d) recovering said hydroxyalkyl sulfonated polymer from said cement; (e) adding about 5 to about 200 parts per hundred by weight of a non-polar process oil to 100 parts of said hydroxyalkylated sulfonated polymer to form a blend of said oil and said hydroxyalkyl sulfonated polymer; and (f) reacting said blend of said oil and said hydroxyalkyl sulfonated polymer with a metal containing base to form a neutralized sulfonated elastomeric polymer and a hydroxyalkyl carboxylate ester having the formula: ##STR7##
Claim 3
Dependent Claim
20 words
A process according to claim 1, wherein said elastomeric polymer has about 0.1 to about 10 mole percent olefinic unsaturation.
Claim 4
Dependent Claim
25 words
A process according to claim 1, wherein said elastomeric polymer is selected from the group consisting essentially of EPDM elastomers, butyl rubbers, and mixtures thereof.
Claim 5
Dependent Claim
43 words
A process according to claim 3, wherein said EPDM elastomer consists essentially of about 45 to about 80 weight percent of ethylene, from about 10 to about 53 wt.% of an alpha-olefin, and about 2 to about 10 wt.% of a diene monomer.
Claim 6
Dependent Claim
12 words
A process according to claim 4, wherein said diene monomer is non-conjugated.
Claim 7
Dependent Claim
30 words
A process according to claim 5, wherein said diene monomer is selected from the group consisting essentially of 1,4-hexadiene, dicyclopentadiene, alkenyl substituted norbornenes, alkylidene substituted norbornenes, methylene norbornene, and tetrahydroindiene.
Claim 8
Dependent Claim
11 words
A process according to claim 4, wherein said diene is 1,4-hexadiene.
Claim 9
Dependent Claim
11 words
A process according to claim 4, wherein said diene is 5-ethylidene-2-norbornene.
Claim 10
Dependent Claim
35 words
A process according to claim 1, wherein said elastomeric polymer has an Mn of about 10,000 to about 200,000 and a Mooney viscosity at 212° F. at 8 minutes of about 5 to about 60.
Claim 11
Dependent Claim
41 words
A process according to claim 1, wherein said sulfonating agent is selected from the group consisting essentially of a mixture of sulfuric acid and acetic anhydride, an acyl sulfate, complexes of sulfur trioxide donor with a Lewis base and mixtures thereof.
Claim 12
Dependent Claim
22 words
A process according to claim 1, wherein said sulfonation occurs in a temperature range of about -100° C. to about 100° C.
Claim 13
Dependent Claim
30 words
A process according to claim 1, wherein said solvent is selected from the group consisting essentially of halogenated aliphatic hydrocarbons, halogenated aromatic hydrocarbons, aromatic hydrocarbons, aliphatic hydrocarbons and mixtures thereof.
Claim 14
Dependent Claim
34 words
A process according to claim 1, wherein said acid form of said sulfonated elastomeric polymer contains about 10 to about 50 meq SO 3 H groups per 100 grams of said sulfonated elastomeric polymer.
Claim 15
Dependent Claim
24 words
A process according to claimm 1, wherein said process oil is selected from the group consisting essentially of aromatics, naphthenics, paraffinics and mixtures thereof.
Claim 16
Dependent Claim
21 words
A process according to claim 1, wherein said process oil is a paraffinic oil having an Mn of at least 300.
Claim 17
Dependent Claim
19 words
A process according to claim 1, wherein said process oil has less than about 6 wt.% of polar compounds.
Claim 18
Dependent Claim
30 words
A process according to claim 1, wherein said process oil is incorporated into said neutralized sulfonated elastomeric polymer at a concentration level of less than about 200 parts per hundred.
Claim 19
Dependent Claim
20 words
A process according to claim 1, wherein said recovery of said hydroxyalkyl sulfonate from said cement further includes steam stripping.
Claim 20
Dependent Claim
72 words
A process according to claim 1, wherein said neutralized sulfonated elastomeric polymer has about 15 to about 40 meq. SO 3 H groups per 100 grams of said sulfonated elastomeric polymer, at least 90 percent of said hydroxyalkyl sulfonate groups being neutralized with a metal counterion selected from the group consisting essentially of lead, aluminum, iron, antimony, Groups I-A, II-A, I-B and II-B of the Periodic Table of Elements and mixtures thereof.
Claim 21
Dependent Claim
52 words
A process according to claim 1, wherein said neutralizing agent is a metallic salt of a carboxylic acid, a metal ion of said metallic salt being selected from the group consisting essentially of iron, lead, aluminum, antimony, Groups I-A, II-A, I-B and II-B of the Periodic Table of Elements and mixtures thereof.
Claim 22
Dependent Claim
126 words
A solid, gel-free elastomeric blend composition consisting essentially of: (a) 100 parts by weight of a neutralized sulfonated elastomeric polymer having about 10 to about 50 meq. of sulfonate groups per 100 grams of said polymer, at least 90 percent of said sulfonate groups being neutralized with a metal counterion; (b) about 2 to about 50 parts per hundred of a hydroxyalkyl carboxylate ester having the formula: ##STR8## wherein R 1 , R 2 , R 3 and R 4 are independently selected from the group consisting of hydrogen, C 1 to C 18 straight and branched chain acyclic, alicyclic, aryl, alkylaryl, and arylalkyl groups and functional derivatives thereof and mixtures thereof; and (c) about 5 to about 200 parts per hundred of a process oil.
Claim 23
Dependent Claim
126 words
A solid, gel-free elastomeric blend composition consisting essentially of: (a) 100 parts by weight of a neutralized sulfonated elastomeric polymer having about 10 to about 50 meq. of sulfonate groups per 100 grams of said polymer, at least 90 percent of said sulfonate groups being neutralized with a metal counterion; (b) about 2 to about 50 parts per hundred of a hydroxyalkyl carboxylate ester having the formula: ##STR8## wherein R 1 , R 2 , R 3 and R 4 are independently selected from the group consisting of hydrogen, C 1 to C 18 straight and branched chain acyclic, alicyclic, aryl, alkylaryl, and arylalkyl groups and functional derivatives thereof and mixtures thereof; and (c) about 5 to about 200 parts per hundred of a process oil.
Claim 24
Dependent Claim
21 words
A composition according to claim 21, wherein said concentration of said process oil is less than about 150 parts per hundred.
Claim 25
Dependent Claim
20 words
A composition according to claim 21, wherein said process oil has less than about 6 wt.% of polar type compounds.
Claim 26
Dependent Claim
18 words
A composition according to claim 21, wherein said process oil has an Mn or about at least 300.
Claim 27
Dependent Claim
22 words
A composition according to claim 21, wherein said process oil is selected from the group consisting essentially of paraffinics, napthenics and aromatics.
Claim 28
Dependent Claim
21 words
A composition according to claim 21, wherein said process oil is a paraffinic having an Mn of at least about 300.
Claim 29
Dependent Claim
29 words
A composition according to claim 21, wherein said sulfonated elastomeric polymer is derived from an unsulfonated elastomeric polymer selected from the group consisting of butyl rubber, and EPDM terpolymers.
Claim 30
Dependent Claim
42 words
A composition according to claim 27, wherein said EPDM terpolymer consists essentially of about 45 to about 80 wt.% of ethylene, from about 10 to about 53 wt.% of an alpha-olefin, and about 2 to about 10 wt.% of a diene monomer.
Claim 31
Dependent Claim
11 words
A composition according to claim 28, wherein said alpha-olefin is propylene.
Claim 32
Dependent Claim
11 words
A composition according to claim 28, wherein said diene is non-conjugated.
Claim 33
Dependent Claim
30 words
A composition according to claim 28, wherein said diene is selected from the group consisting essentially of 1,4 hexadiene, dicyclopentadiene, alkenyl substituted norbornenes, alkylidene substituted norbornenes, methylene norbornene, and tetrahydroindene.
Claim 34
Dependent Claim
11 words
A composition according to claim 28, wherein said diene is 5-ethylidene-2-norbornene.
Claim 35
Dependent Claim
37 words
A composition according to claim 21, wherein said metal counterion is selected from the group consisting essentially of lead, aluminum, iron, antimony, Groups I-A, II-A, I-B and II-B of the Periodic Table of Elements and mixtures thereof.
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) | 1981-10-02 | 1982-04-03 | 1982-10-03 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-10-02 | 1986-04-03 | 1986-10-03 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-10-02 | 1990-04-03 | 1990-10-03 | $7700.00 | Window Closed / Lapsed |