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Process for the modification of aromatic polymers via Friedel-Crafts reactions to produce novel polymers and the use thereof

Assignee: Standard Oil Co
•
Filing: 1986-01-30
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Granted: 1987-08-04
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Expires: 2006-01-30
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Abstract

Abstract A process for the addition of pendant groups to polyarylenes comprises the steps of charging a reaction vessel with a solution of a polyarylene and a Friedel-Crafts catalyst; said polyarylene having the formula ##STR1## adding to the reaction vessel a pendant forming group G, wherein G is selected from the group consisting of sulfonyl halides, sulfonamide halides, alkylhalides, acylhalides and phosphorus acid halides; heating the contents of the reaction vessel to form a substituted polyarylene having the formula ##STR2## and thereafter recovering the substituted polyarylene. The substituted polyarylenes are novel and have utility as a semipermeable membrane and a process for the separation of gases therewith is also provided.

Inventors

  • 👤 Elena S. Percec
  • 👤 George S. Li

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-01 10:25
CPC Classifications
C; C08; C08G; C08G75/00; C08G75/02; C08G75/0204; C08G75/0286; B; B01; B01D; B01D71/00; B01D71/06; B01D71/50; B01D71/52; B01D71/522; B01D71/66; B01D71/69; C08G65/00; C08G65/34; C08G65/48; C08G65/485; Y; Y10; Y10S; Y10S525/00; Y10S525/905

Claims Analysis

Total Claims: 17
Claim 1
Independent Claim 205 words
Novel substituted polyarylene polymers as semipermeable membranes useful for the separation of gases from a mixture containing at least two fractions into enriched fractions of each having the formula ##STR21## wherein each R is independently a C 1 to C 8 aliphatic or a C 5 to C 7 cycloaliphatic radical, an aryl radical having the formula ##STR22## wherein each R 1 is independently a C 1 to C 8 aliphatic radical and p is an integer of 0 to 4, each radical being free of a tertiary alpha-carbon atom; A is hydrogen, halogen, an aliphatic or an aryl radical; Y is a dilvalent oxygen or sulflur atom or a carbonate group; n is an integer of from about 75 to about 10,000; and wherein G is present in at least five percent of said polyarylene units and is selected from the group consisting of alkyl sulfonyl groups having the formula ##STR23## where R a is a C 1 to C 20 aliphatic radical; sulfonamide groups having the formula ##STR24## where R 2 and is a C 1 to C 20 aliphatic or aryl radical of the formula ##STR25## or a naphthyl radical where R 1 and p are as described above and phosphorus groups.
Claim 2
Dependent Claim 205 words
Novel substituted polyarylene polymers as semipermeable membranes useful for the separation of gases from a mixture containing at least two fractions into enriched fractions of each having the formula ##STR21## wherein each R is independently a C 1 to C 8 aliphatic or a C 5 to C 7 cycloaliphatic radical, an aryl radical having the formula ##STR22## wherein each R 1 is independently a C 1 to C 8 aliphatic radical and p is an integer of 0 to 4, each radical being free of a tertiary alpha-carbon atom; A is hydrogen, halogen, an aliphatic or an aryl radical; Y is a dilvalent oxygen or sulflur atom or a carbonate group; n is an integer of from about 75 to about 10,000; and wherein G is present in at least five percent of said polyarylene units and is selected from the group consisting of alkyl sulfonyl groups having the formula ##STR23## where R a is a C 1 to C 20 aliphatic radical; sulfonamide groups having the formula ##STR24## where R 2 and is a C 1 to C 20 aliphatic or aryl radical of the formula ##STR25## or a naphthyl radical where R 1 and p are as described above and phosphorus groups.
Claim 3
Dependent Claim 35 words
Novel substituted polyarylene polymers, as set forth in claim 1, wherein Y is oxygen, R is methyl, A is hydrogen and said halogens are selected from the group consisting of F, Cl, Br and I.
Claim 4
Dependent Claim 19 words
Novel substituted polyarylene polymers as set forth in claim 2, wherein R 2a of said alkyl sulfonyl is hexadecyl.
Claim 5
Dependent Claim 18 words
Novel substituted polyarylene polymers as set forth in claim 2, wherein R 2 of said sulfonamide is methyl.
Claim 6
Dependent Claim 43 words
Novel substituted polyarylene polymers as set forth in claim 1, wherein the gases in said mixture are selected from the group consisting of hydrogen, helium, oxygen, nitrogen, carbon monoxide, carbon dioxide, hydrogen sulfide, ammonia, water vapor and C 1 to C 4 hydrocarbons.
Claim 7
Dependent Claim 21 words
Novel substituted polyarylene polymers as set forth in claim 5, wherein said mixture of gases comprises carbon dioxide, methane and nitrogen.
Claim 8
Dependent Claim 221 words
A process for the separation of gases from a mixture containing at least two gases into two fractions, one fraction being enriched with at least one of said gases and the other fraction being depleted in same, comprising the step of: contacting the gaseous mixture with a semipermeable membrane in such a manner that a portion of the gaseous mixture selectively passes through the membrane resulting in the enriched fraction being on one side of the membrane and the depleted fraction being on the other side of the membrane, said semipermeable membrane comprising a substituted polyarylene polymer having the formula ##STR26## wherein each R is independently a C 1 to C 8 aliphatic or a C 5 to C 7 cycloaliphatic radical, an aryl radical having the formula ##STR27## wherein each R 1 is independently a C 1 to C 8 aliphatic radical and p is an integer of 0 to 4, each radical being free of a tertiary alpha-carbon atom; A is hydrogen, halogen, an aliphatic or an aryl radical; Y is a divalent oxygen or sulfur atom or a carbonate group; n is an integer of from about 75 to 10,000; and wherein G is present in at least five percent of said polyarylene units and is selected from the group consisting of alkyl sulfonyl, sulfonamide and phosphorus groups.
Claim 9
Dependent Claim 221 words
A process for the separation of gases from a mixture containing at least two gases into two fractions, one fraction being enriched with at least one of said gases and the other fraction being depleted in same, comprising the step of: contacting the gaseous mixture with a semipermeable membrane in such a manner that a portion of the gaseous mixture selectively passes through the membrane resulting in the enriched fraction being on one side of the membrane and the depleted fraction being on the other side of the membrane, said semipermeable membrane comprising a substituted polyarylene polymer having the formula ##STR26## wherein each R is independently a C 1 to C 8 aliphatic or a C 5 to C 7 cycloaliphatic radical, an aryl radical having the formula ##STR27## wherein each R 1 is independently a C 1 to C 8 aliphatic radical and p is an integer of 0 to 4, each radical being free of a tertiary alpha-carbon atom; A is hydrogen, halogen, an aliphatic or an aryl radical; Y is a divalent oxygen or sulfur atom or a carbonate group; n is an integer of from about 75 to 10,000; and wherein G is present in at least five percent of said polyarylene units and is selected from the group consisting of alkyl sulfonyl, sulfonamide and phosphorus groups.
Claim 10
Dependent Claim 28 words
A process, as set forth in claim 7, wherein said alkyl sulfonyls have the formula ##STR28## where R 2a is a C 1 to C 20 aliphatic radical.
Claim 11
Dependent Claim 46 words
A process, as set forth in claim 7, wherein said sulfonamides have the formula ##STR29## where R 2 is a C 1 to C 20 aliphatic or aryl radical of the formula ##STR30## or a naphthyl radical where R 1 and p are as described above.
Claim 12
Dependent Claim 72 words
A process, as set forth in claim 7, wherein said phosphorus groups have the formula --P--(R.sub.5).sub.3-q where R 5 is selected from the group consisting of R 4 and O-R 4 and mixtures thereof where R 4 is a C 1 to C 20 aliphatic or an aryl radical of the formula ##STR31## where R 1 and p are as described above and q is an integer of from 1 to 3.
Claim 13
Dependent Claim 33 words
A process, as set forth in claim 7, wherein Y is oxygen, R is methyl, A is hydrogen and said halogens are selected from the group consisting of F, Cl, Br and I.
Claim 14
Dependent Claim 17 words
A process, as set forth in claim 8, wherein R 2a of said alkyl sulfonyl is hexadecyl.
Claim 15
Dependent Claim 16 words
A process, as set forth in claim 9, wherein R 2 of said sulfonamide is methyl.
Claim 16
Dependent Claim 41 words
A process, as set forth in claim 11, wherein the gases in said mixture are selected from the group consisting of hydrogen, helium, oxygen, nitrogen, carbon monoxide, carbon dioxide, hydrogen sulfide, ammonia, water vapor and C 1 to C 4 hydrocarbons.
Claim 17
Dependent Claim 19 words
A process, as set forth in claim 14, wherein said mixture of gases comprises carbon dioxide, methane and nitrogen.

References Cited (Backward Citations)

US3350844A Cited
US3780496A Cited
US4427419A Cited
US4431793A Cited
US4488886A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1990-08-03 1991-02-02 1991-08-04 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1994-08-03 1995-02-02 1995-08-04 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1998-08-03 1999-02-02 1999-08-04 $7700.00 Window Closed / Lapsed

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