US3870841A
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US
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Flexible polymeric compositions comprising a normally plastic polymer sulfonated to about 0.2 to about 10 mole % sulfonate
Assignee: ExxonMobil Technology and Engineering Co
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Filing: 1972-10-02
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Granted: 1975-03-11
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Expires: 1992-10-02
Abstract
Abstract Flexible polymeric compositions are prepared by introducing sulfonate groups into a plastic polymer and plasticizing the ionomer so formed. Plasticization may be limited to plasticizing the amorphous backbone. Preferably the ionic domains of the ionomer are also plasticized using a plasticizer which is effective at processing temperature but ineffective at use temperature. The products of this invention are flexible and have utility as simulated leathers, wire coating insulation, etc.
Inventors
- 👤 Henry S Makowski
- 👤 Robert D Lundberg
- 👤 Gopal H Singhal
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 11:57
CPC Classifications
C; C08; C08K; C08K5/00; C08K5/0008; C08K5/0016; C08C; C08C19/00; C08C19/20; C08F; C08F28/00
Claims Analysis
Total Claims: 50
Claim 1
Independent Claim
72 words
A flexible composition comprising: a normally plastic polymer sulfonated to about 0.2 to about 10 mole percent sulfonate, said plastic polymer being substantially amorphous and having a softening point between about 25*C and 260*C; and b. about 20 to about 500 parts per hundred by weight based on the sulfonated plastic polymer of a polymer chain plasticizer, said plasticizer being a normally liquid compound having a boiling point of at least 120*C.
Claim 2
Dependent Claim
72 words
A flexible composition comprising: a normally plastic polymer sulfonated to about 0.2 to about 10 mole percent sulfonate, said plastic polymer being substantially amorphous and having a softening point between about 25*C and 260*C; and b. about 20 to about 500 parts per hundred by weight based on the sulfonated plastic polymer of a polymer chain plasticizer, said plasticizer being a normally liquid compound having a boiling point of at least 120*C.
Claim 3
Dependent Claim
72 words
A FLEXIBLE COMPOSITION COMPRISING: A NORMALLY PLASTIC POLYMER SULFONATED TO ABOUT 0.2 TO ABOUT 10 MOLE PERCENT SULFONATE, SAID PLASTIC POLYMER BEING SUBSTANTIALLY AMORHPOUS AND HAVING A SOFTENING POINT BETWEEN ABOUT 25*C AND 260*C; AND B. ABOUT 20 TO ABOUT 500 PARTS PER HUNDRED BY WEIGHT BASED ON THE SULFONATED PLASTIC POLYMER OF A POLYMER CHAIN PLASTICZER, SAID PLASTICIZER BEING A NORMALLY LIQUID COMPPOUND HAVING A BOILING POINT OF AT LEAST 12*C.
Claim 4
Dependent Claim
72 words
A FLEXIBLE COMPOSITION COMPRISING: A NORMALLY PLASTIC POLYMER SULFONATED TO ABOUT 0.2 TO ABOUT 10 MOLE PERCENT SULFONATE, SAID PLASTIC POLYMER BEING SUBSTANTIALLY AMORHPOUS AND HAVING A SOFTENING POINT BETWEEN ABOUT 25*C AND 260*C; AND B. ABOUT 20 TO ABOUT 500 PARTS PER HUNDRED BY WEIGHT BASED ON THE SULFONATED PLASTIC POLYMER OF A POLYMER CHAIN PLASTICZER, SAID PLASTICIZER BEING A NORMALLY LIQUID COMPPOUND HAVING A BOILING POINT OF AT LEAST 12*C.
Claim 5
Dependent Claim
13 words
The composition of claim 1 wherein the chain plasticizer is a phosphate ester.
Claim 6
Dependent Claim
81 words
The composition of claim 1 wherein the sulfonate group is neutralized with a compound selected from the group consisting of (1) ammonia, (2) primary amines, (3) secondary amines, (4) tertiary amines, and (5) a metal compound wherein the metal compound is a salt, hydroxide, oxide, alkoxide or carboxylate wherein the metal is selected from the group consisting of lead, tin, antimony and metals of Groups IA, IIA, IB and IIB of the Periodic Table of the Elements and (6) mixtures thereof.
Claim 7
Dependent Claim
36 words
The composition of claim 3 wherein the sulfonate content is about 0.5 to about 6 mole percent and the chain plasticizer is present at about 25 to about 250 parts per hundred based on the polymer.
Claim 8
Dependent Claim
40 words
The composition of claim 4 wherein the number of sulfonate groups per 100 monomer units is from about 1.0 to about 3 and the chain plasticizer is included in the composition at about 30 to about 100 parts per hundred.
Claim 9
Dependent Claim
34 words
The composition of claim 3 wherein the plastic polymer is a polymer of at least one monomer selected from the group consisting of vinyl aromatics, vinyl acylates, alkyl methacrylates, vinyl cyanides and mixtures thereof.
Claim 10
Dependent Claim
23 words
The composition of claim 6 wherein the chain plasticizer is a normally liquid organic compound having a boiling point of at least 120*C.
Claim 11
Dependent Claim
35 words
The composition of claim 6 wherein the plastic polymer is a polymer of at least one monomer selected from the group consisting of styrene, t-butyl styrene, vinyl toluene, chlorostyrene, dichlorostyrene, alpha-methyl styrene and mixtures thereof.
Claim 12
Dependent Claim
23 words
The composition of claim 8 wherein the chain plasticizer is a normally liquid organic compound having a boiling point of at least 120*C.
Claim 13
Dependent Claim
19 words
The composition of claim 6 wherein the polymer is the polymerization product of at least two of said monomers.
Claim 14
Dependent Claim
56 words
The composition of claim 3 wherein the plastic polymer is the polymerization reaction product of (1) at least one monomer selected from the group consisting of styrene, t-butyl styrene, vinyl toluene, chlorostyrene, dichlorostyrene and alpha-methyl styrene and (2) a diene wherein the mole percent unsaturation of the polymer is about 1 to about 15 mole percent.
Claim 15
Dependent Claim
22 words
The composition of claim 11 wherein the plasticizer is a normally liquid organic compound having a boiling point of at least 120*C.
Claim 16
Dependent Claim
13 words
The composition of claim 11 wherein the diene is isoprene, butadiene or 5-ethylidene-2-norbornene.
Claim 17
Dependent Claim
13 words
The composition of claim 13 wherein the monomer is t-butylstyrene, chlorostyrene or dichlorostyrene.
Claim 18
Dependent Claim
30 words
The composition of claim 3 wherein the polymer is polystyrene and the chain plasticizer is a dialkyl phthalate wherein the alkyl group comprises about 1 to about 10 carboN atoms.
Claim 19
Dependent Claim
18 words
The composition of claim 15 wherein the phthalate is dibutyl phthalate, dihexyl phthalate, dioctyl phthalate, or mixtures thereof.
Claim 20
Dependent Claim
29 words
The composition of claim 3 wherein the polymer is t-butyl styrene and the chain plasticizer is a dialkyl phthalate wherein the alkyl groups comprise at least 5 carbon atoms.
Claim 21
Dependent Claim
29 words
The composition of claim 3 wherein the polymer is t-butyl styrene and the chain plasticizer is a non-volatile normally liquid hydrocarbon with a solubility parameter of less than 9.0.
Claim 22
Dependent Claim
14 words
The composition of claim 18 wherein the chain plasticizer is a rubber process oil.
Claim 23
Dependent Claim
26 words
The composition of claim 3 wherein the polymer is t-butyl styrene and the chain plasticizer is an organic acid ester comprising at least 10 carbon atoms.
Claim 24
Dependent Claim
32 words
The composition of claim 20 wherein the ester is a polyester of an aliphatic glycol and an aliphatic dibasic acid wherein the ratio of methylene groups to oxygen is at least 5.
Claim 25
Dependent Claim
63 words
The composition of claim 3 wherein a domain plasticizer at a level of about 1 to about 50 weight percent based on sulfonated polymer is included, said domain plasticizer being a compound which acts to reversibly disrupt the association of the sulfonate groups at the temperature of forming the flexible compositions and is inactive at the temperature of use of the flexible compositions.
Claim 26
Dependent Claim
13 words
The composition of claim 22 wherein the domain plasticizer is a fugitive plasticizer.
Claim 27
Dependent Claim
26 words
The composition of claim 23 wherein the domain plasticizer is an alcohol, an amine or a mercaptan having a boiling point of less than 125* C.
Claim 28
Dependent Claim
17 words
The composition of claim 22 wherein the domain plasticizer has a boiling point of greater than 120*C.
Claim 29
Dependent Claim
23 words
The composition of claim 25 wherein the domain plasticizer is a normally liquid organic compound having a solubility parameter of at least 9.5.
Claim 30
Dependent Claim
24 words
The composition of claim 25 wherein the domain plasticizer is a compound containing functional groups with a bond moment of at least 0.6 Debyes.
Claim 31
Dependent Claim
44 words
The composition of claim 25 wherein the domain plasticizer is an alcohol, a carboxylic acid ester, a carboxylic acid amide, an amine, an alkylated area, guanidine, a hydrocarbon-substituted guanidine, a sulfonamide, a sulfone, a sulfonate, a phosphate, a phosphonate, a phosphonamide, or a phosphoramide.
Claim 32
Dependent Claim
53 words
The composition of claim 28 wherein the domain plasticizer is (1) N-ethyltoluenesulfonamide, (2) ditolyl guanidine, or (3) a metal compound wherein the metal compound is a carboxylate, sulfonate or phosphonate and the metal is lead, tin, antimony or a metal of Groups IA, IIA, IB, IIB of the Periodic Table of the Elements.
Claim 33
Dependent Claim
13 words
The composition of claim 29 wherein the metal carboxylate is a metal stearate.
Claim 34
Dependent Claim
11 words
The composition of claim 30 wherein the stearate is zinc stearate.
Claim 35
Dependent Claim
34 words
The composition of claim 3 wherein the polymer is a vinyl acetate copolymer wherein vinylacetate is copolymerized with at least one monomer selected from the group consisting of vinyl aromatics, dienes and mixtures thereof.
Claim 36
Dependent Claim
11 words
The composition of claim 32 wherein the vinyl aromatic is styrene.
Claim 37
Dependent Claim
13 words
The composition of claim 32 wherein the diene is butadiene, isoprene or 5-ethylidene-2-norbornene.
Claim 38
Dependent Claim
31 words
The composition of claim 32 wherein the chain plasticizer is dinonyl adipate, triethyl citrate, dioctyl fumarate, dibutyl maleate, tributyl phosphate, tricresyl phosphate, diethyl phthalate, dibutyl phthalate, dicyclohexyl phthalate or mixtures thereof.
Claim 39
Dependent Claim
30 words
The composition of claim 3 wherein the polymer is methyl methacrylate copolymerized with a minor amount of a second monomer wherein said monomer is a vinyl aromatic or a diene.
Claim 40
Dependent Claim
19 words
The composition of claim 36 wherein the vinyl aromatic is styrene and the diene is butadiene, isoprene or 5-ethylidene-2-norbornene.
Claim 41
Dependent Claim
14 words
The composition of claim 3 wherein the metal is sodium, potassium, calcium or barium.
Claim 42
Dependent Claim
28 words
The composition of claim 3 whereIn the polymer is a copolymer of styrene and a second monomer selected from the group consisting of alkyl acrylates or alkyl methacrylates.
Claim 43
Dependent Claim
11 words
The composition of claim 39 wherein the second monomer is methylmethacrylate.
Claim 44
Dependent Claim
32 words
The composition of claim 3 wherein the polymer is a vinyl acetate copolymer wherein vinylacetate is copolymerized with a second monomer wherein said second monomer is a sulfonic acid or sulfonate compound.
Claim 45
Dependent Claim
12 words
The composition of claim 41 wherein the second monomer is 2-sulfo-ethyl methacrylate.
Claim 46
Dependent Claim
31 words
The composition of claim 41 wherein the chain plasticizer in dinonyl adipate, triethyl citrate, dioctyl fumarate, dibutyl maleate, tributyl phosphate, tricresyl phosphate diethyl phthalate, dibutyl phthalate, dicyclohexyl phthalate or mixtures thereof.
Claim 47
Dependent Claim
130 words
A processable composition comprising a. a normally plastic polymer sulfonated to about 0.2 to about 10 mole percent sulfonate, said plastic polymer being substantially amorphous and having a softening point between about 25*C. and 260*C.; b. about 20 to about 500 parts per hundred by weight based on the sulfonated plastic polymer of a polymer chain plasticizer; and c. a fugitive domain plasticizer, said fugitive plasticizer being included at about 1 to about 50 weight percent based on sulfonated polymer, said fugitive domain plasticizer being a compound which acts to disrupt the association of the sulfonate groups at the temperature of forming said processable composition and has a boiling point of less than 120*C.; whereby removal of the fugitive plasticizer converts the processable composition to a flexible substantially intractable composition.
Claim 48
Dependent Claim
130 words
A processable composition comprising a. a normally plastic polymer sulfonated to about 0.2 to about 10 mole percent sulfonate, said plastic polymer being substantially amorphous and having a softening point between about 25*C. and 260*C.; b. about 20 to about 500 parts per hundred by weight based on the sulfonated plastic polymer of a polymer chain plasticizer; and c. a fugitive domain plasticizer, said fugitive plasticizer being included at about 1 to about 50 weight percent based on sulfonated polymer, said fugitive domain plasticizer being a compound which acts to disrupt the association of the sulfonate groups at the temperature of forming said processable composition and has a boiling point of less than 120*C.; whereby removal of the fugitive plasticizer converts the processable composition to a flexible substantially intractable composition.
Claim 49
Dependent Claim
25 words
The composition of claim 44 wherein the domain plasticizer is an alcohol, an amine or a mercaptan having a boiling point of less than 125*C.
Claim 50
Dependent Claim
25 words
The composition of claim 44 wherein the fugitive plasticizer is methyl alcohol, isopropyl alcohol, n-butyl alcohol, triethyl phosphate, ethyl amine, triethyl amine, or ethane thiol.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1978-03-10 | 1978-09-09 | 1979-03-11 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1982-03-10 | 1982-09-09 | 1983-03-11 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1986-03-10 | 1986-09-09 | 1987-03-11 | $7700.00 | Window Closed / Lapsed |