US4208486A
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Stabilization of organic amide solvents and polymer solutions thereof
Assignee: ExxonMobil Technology and Engineering Co
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Filing: 1978-12-08
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Granted: 1980-06-17
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Expires: 1998-12-08
Abstract
Abstract Organic amides, solutions of polymers thereof, which polymers are subject to hydrolysis and degradation in the presence of amines, and polymers isolated therefrom are stabilized by the presence of aromatic sulfonic acid esters of aliphatic, arylaliphatic and alicyclic alcohols and polyols.
Inventors
- 👤 Tad L. Patton
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 19:36
CPC Classifications
C; C08; C08L; C08L79/00; C08L79/04; C08L79/08; C08K; C08K5/00; C08K5/36; C08K5/41; C08K5/42
Claims Analysis
Total Claims: 38
Claim 1
Independent Claim
51 words
A solution of polymers in an organic amide solvent stabilized against degradation in the presence of amines, containing dissolved therein a stabilizing amount of an aromatic sulfonic acid ester of an aliphatic, arylaliphatic or alicyclic polyol, the polymers being selected from the group consisting of polyparabanic acids, poly(iminoimidazolidinediones), polyimides, and polyhydantoins.
Claim 2
Dependent Claim
51 words
A solution of polymers in an organic amide solvent stabilized against degradation in the presence of amines, containing dissolved therein a stabilizing amount of an aromatic sulfonic acid ester of an aliphatic, arylaliphatic or alicyclic polyol, the polymers being selected from the group consisting of polyparabanic acids, poly(iminoimidazolidinediones), polyimides, and polyhydantoins.
Claim 3
Dependent Claim
84 words
The stabilized solution of claim 1, wherein the aromatic sulfonic acid ester is a compound having one of the following structures: ##STR5## wherein AR is an unsubstituted or substituted aryl or alkylaryl group having 6 to 18 carbon atoms, wherein substituents are selected from alkoxy, halogen, alkoxy carbonyl, acyl, nitro, hydroxy and carbonyl; R is a divalent aliphatic, arylaliphatic or alicyclic group; wherein R' is a divalent aliphatic group having 2 to 4 carbon atoms; and n is an integer from 2 to 100.
Claim 4
Dependent Claim
12 words
The stabilized solution of claim 2, wherein the polymers are polyparabanic acids.
Claim 5
Dependent Claim
53 words
The stabilized solution of claim 2, wherein the aromatic sulfonic acid ester is selected from the group consisting of ethylene bis (benzene sulfonate), ethylene bis (p-toluenesulfonate), trimethylene bis (p-toluenesulfonate), tetramethylene bis (p-toluenesulfonate), ethylene (p-toluenesulfonate, benzene sulfonate), xylylene bis (benzene sulfonate), xylylene bis (p-toluenesulfonate), cyclohexylene bis (p-toluenesulfonate), ethylene bis (naphthalene sulfonate), and mixtures thereof.
Claim 6
Dependent Claim
16 words
The stabilized solution of claim 2, wherein the aromatic sulfonic acid ester is ethylene bis (p-toluenesulfonate).
Claim 7
Dependent Claim
33 words
The stabilized solution of claim 1, wherein said aromatic sulfonic acid ester is present in said polymer solution in an amount sufficient to react with all amines present and generated in said solution.
Claim 8
Dependent Claim
23 words
The stabilized solution of claim 1, wherein the organic amide solvent is selected from dimethylformamide, diethylformamide, N,N-dimethylacetamide, N,N-diethylacetamide, N,N-dimethylpropionamide, N,N-dimethylbutyramide, N-methylpyrrolidone and N-ethylpyrrolidone.
Claim 9
Dependent Claim
18 words
The stabilized solution of claim 7, wherein the organic amide solvent is selected from dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.
Claim 10
Dependent Claim
31 words
The stabilized solution of claim 3, wherein said organic amide solvent is dimethylformamide, said polymer is a polymer of 1,4-phenylene-methylene-1,4-phenylene-1,3-(imidazolidine-2,3,4-trione), and said aromatic sulfonic acid ester is ethylene bis (p-toluene sulfonate).
Claim 11
Independent Claim
59 words
A method of stabilizing solutions of polymers in organic amide solvents, said polymers being subjected to degradation in the presence of amines, comprising dissolving in said solution a stabilizing amount of an aromatic sulfonic acid ester of an aliphatic, arylaliphatic or alicyclic polyol, wherein the polymers are selected from the group consisting of polyparabanic acids, poly(iminoimidazolidinediones), polyimides, and polyhydantoins.
Claim 12
Independent Claim
59 words
A method of stabilizing solutions of polymers in organic amide solvents, said polymers being subjected to degradation in the presence of amines, comprising dissolving in said solution a stabilizing amount of an aromatic sulfonic acid ester of an aliphatic, arylaliphatic or alicyclic polyol, wherein the polymers are selected from the group consisting of polyparabanic acids, poly(iminoimidazolidinediones), polyimides, and polyhydantoins.
Claim 13
Dependent Claim
28 words
The method of claim 10, wherein said aromatic sulfonic acid ester is dissolved in the organic amide solvent prior to dissolving said polymer in said organic amide solvent.
Claim 14
Dependent Claim
11 words
The method of claim 10, wherein the polymers are polyparabanic acids.
Claim 15
Dependent Claim
82 words
The method of claim 10, wherein the aromatic sulfonic acid ester is a compound having one of the following structures: ##STR6## wherein AR is unsubstituted or substituted aryl or alkylaryl group having 6 to 18 carbon atoms, wherein substituents are selected from alkoxy, halogen, alkoxy carbonyl, acyl, nitro, hydroxy and carbonyl; R is a divalent aliphatic, arylaliphatic or alicyclic group; wherein R' is a divalent aliphatic group having 2 to 4 carbon atoms; and n is an integer from 2 to 100.
Claim 16
Dependent Claim
52 words
The method of claim 13, wherein the aromatic sulfonic acid ester is selected from the group consisting of ethylene bis (benzene sulfonate), ethylene bis (p-toluenesulfonate), trimethylene bis (p-toluenesulfonate), tetramethylene bis (p-toluenesulfonate), ethylene (p-toluenesulfonate, benzene sulfonate), xylylene bis (benzene sulfonate), xylylene bis (p-toluenesulfonate), cyclohexylene bis (p-toluenesulfonate), ethylene bis (naphthalene sulfonate), and mixtures thereof.
Claim 17
Dependent Claim
15 words
The method of claim 10, wherein the aromatic sulfonic acid ester is ethylene bis (p-toluenesulfonate).
Claim 18
Dependent Claim
32 words
The method of claim 10, wherein said aromatic sulfonic acid ester is present in said polymer solution in an amount sufficient to react with all amines present and generated in said solution.
Claim 19
Dependent Claim
22 words
The method of claim 10, wherein the organic amide solvent is selected from dimethylacetamide, diethylformamide, N,N-dimethylacetamide, N,N-diethylacetamide, N,N-dimethylpropionamide, N,N-dimethylbutyramide, N-methylpyrrolidone and N-ethylpyrrolidone.
Claim 20
Dependent Claim
17 words
The method of claim 17, wherein the organic amide solvent is selected from dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.
Claim 21
Dependent Claim
30 words
The method of claim 12, wherein said organic amide solvent is dimethylformamide, said polymer is a polymer of 1,4-phenylenemethylene-1,4-phenylene-1,3- (imidazolidine-2,4,5-trione), and said aromatic sulfonic acid ester is ethylene bis p-toluenesulfonate.
Claim 22
Dependent Claim
43 words
A stabilized polymer subject to degradation in the presence of amines containing a stabilizing amount of an aromatic sulfonic acid ester of an aliphatic, arylaliphatic or alicyclic polyol the polymers being selected from the group consisting of polyparabanic acids, poly(iminoimidazolidinediones), polyimides, and polyhydantoins.
Claim 23
Dependent Claim
43 words
A stabilized polymer subject to degradation in the presence of amines containing a stabilizing amount of an aromatic sulfonic acid ester of an aliphatic, arylaliphatic or alicyclic polyol the polymers being selected from the group consisting of polyparabanic acids, poly(iminoimidazolidinediones), polyimides, and polyhydantoins.
Claim 24
Dependent Claim
12 words
The stabilized polymer of claim 20, wherein the polymers are polyparabanic acids.
Claim 25
Dependent Claim
84 words
The stabilized polymer of claim 20, wherein the aromatic sulfonic acid ester is a compound having one of the following structures: ##STR7## wherein AR is an unsubstituted or substituted aryl or alkylaryl group having 6 to 18 carbon atoms, wherein substituents are selected from alkoxy, halogen, alkoxy carbonyl, acyl, nitro hydroxy and carbonyl; R is a divalent aliphatic, arylaliphatic or alicyclic group; wherein R' is a divalent aliphatic group having 2 to 4 carbon atoms; and n is an integer from 2 to 100.
Claim 26
Dependent Claim
53 words
The stabilized polymer of claim 22, wherein the aromatic sulfonic acid ester is selected from the group consisting of ethylene bis (benzene sulfonate), ethylene bis (p-toluenesulfonate), trimethylene bis (p-toluenesulfonate), tetramethylene bis (p-toluenesulfonate), ethylene (p-toluenesulfonate, benzene sulfonate), xylylene bis (benzene sulfonate), xylylene bis (p-toluenesulfonate), cyclohexylene bis (p-toluenesulfonate), ethylene bis (naphthalene sulfonate), and mixtures thereof.
Claim 27
Dependent Claim
16 words
The stabilized polymer of claim 23, wherein the aromatic sulfonic acid ester is ethylene bis (p-toluenesulfonate).
Claim 28
Dependent Claim
33 words
The stabilized polymer of claim 20, wherein said aromatic sulfonic acid ester is present in said polymer solution in an amount sufficient to react with all amines present and generated in said polymer.
Claim 29
Dependent Claim
18 words
The stabilized polymer of claim 20, wherein said polymer contains a residual amount of an organic amide solvent.
Claim 30
Dependent Claim
22 words
The stabilized polymer of claim 20, wherein the organic amide solvent is selected from dimethylformamide, diethylformamide, N,N-dimethylacetamide, N,N-diethylacetamide, N,N-dimethylpropionamide, N,N-dimethylbutyramide,N,-methylpyrrolidone and N-ethylpyrrolidone.
Claim 31
Dependent Claim
18 words
The stabilized polymer of claim 20, wherein the organic amide solvent is selected from dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.
Claim 32
Dependent Claim
32 words
The stabilized polymer of claim 21, wherein said organic amide solvent is dimethylformamide, said polymer is a polymer of 1,4- phenylene-methylene-1,4-phenylene-1,3-(imidazolidine-2,4,5-trione), and said aromatic sulfonic acid ester is ethylene bis (p-toluene sulfonate).
Claim 33
Dependent Claim
34 words
Stabilized films of polyparabanic acid subject to degradation in the presence of amines, said film containing a stabilizing amount of an aromatic sulfonic acid ester of an aliphatic, arylaliphatic or alicyclic alcohol or polyol.
Claim 34
Dependent Claim
34 words
Stabilized films of polyparabanic acid subject to degradation in the presence of amines, said film containing a stabilizing amount of an aromatic sulfonic acid ester of an aliphatic, arylaliphatic or alicyclic alcohol or polyol.
Claim 35
Dependent Claim
102 words
The stabilized films of claim 30 wherein the aromatic sulfonic acid ester is a compound having one of the following structures: ##STR8## wherein AR is an unsubstituted or substituted aryl or alkylaryl group having 6 to 18 carbon atoms, wherein substitutents are selected from alkoxy, halogen, alkoxy carbonyl, acyl, nitro, hydroxy and carbonyl; wherein R is a divalent aliphatic, arylaliphatic or alicyclic group; wherein R' is a divalent aliphatic group having 2 to 4 carbon atoms; and n is an integer of from 2 to 100; and R" is an aliphatic, arylaliphatic or alicyclic group having from 1 to 18 carbon atoms.
Claim 36
Dependent Claim
15 words
The stabilized films of claim 31 wherein said aromatic sulfonic acid ester is methyl p-toluenesulfonate.
Claim 37
Dependent Claim
14 words
The stabilized films of claim 31 wherein said film is a clear solid film.
Claim 38
Dependent Claim
13 words
The stabilized films of claim 31 wherein said film is a microcellular film.
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) | 1983-06-17 | 1983-12-17 | 1984-06-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-06-17 | 1987-12-17 | 1988-06-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-06-17 | 1991-12-17 | 1992-06-17 | $7700.00 | Window Closed / Lapsed |