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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
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Filing: 1984-10-03
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Granted: 1986-06-24
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Expires: 2004-10-03
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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 catalysts; 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 2026-10-30 17:46
CPC Classifications
B; B01; B01D; B01D71/00; B01D71/06; B01D71/52; B01D71/522; B01D71/50; B01D71/66; C; C08; C08G; C08G65/00; C08G65/34; C08G65/48; C08G65/485; C08G75/00; C08G75/02; C08G75/0204; C08G75/0286; Y; Y10; Y10S; Y10S525/00; Y10S525/905; Y10T; Y10T428/00; Y10T428/29; Y10T428/2913; Y10T428/2973; Y10T428/2975

Claims Analysis

Total Claims: 11
Claim 1
Independent Claim 347 words
A process for the addition of pendant groups to polyarylene comprising the steps of charging a reaction vessel with a solution of a polyarylene and a Friedel-Crafts catalyst, said polyarylene having the formula ##STR21## wherein said 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## where said each R 1 is independently a C 1 to C 8 aliphatic radical and p is an integer of 0 to 4, each said 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 and n is an integer of from about 75 to about 10,000; adding to said reaction vessel a pendant forming group G, wherein G is derived from a compound selected from the group consisting of sulfonyl halides having the formula ##STR23## where X is a halogen and R 2 is a C 1 to C 20 aliphatic or a naphthyl radical; a sulfonamide halide having the formula ##STR24## where R 2 is as above and can be the same or different; alkylhalides having the formula R.sub.3 --X where X is a halogen and R 3 is a C 5 to C 20 aliphatic radical; acylhalides having the formula ##STR25## where X is a halogen and R 4 is a C 5 to C 20 aliphatic or an aryl radical of the formula ##STR26## and where R 1 and p are as described above, phosphorus acid halides having the formula X.sub.q --P--(R.sub.5).sub.3-q where X is a halogen; R 5 is selected from the group consisting of R 4 , O--R 4 and mixtures thereof and q is an integer of from 1 to 3; heating the contents of said reaction vessel to form a substituted polyarylene having the formula ##STR27## where G is present in at least five percent of the polyarylene units and R, A, Y, G and n are as described and, thereafter recovering said substituted polyarylene.
Claim 2
Dependent Claim 347 words
A process for the addition of pendant groups to polyarylene comprising the steps of charging a reaction vessel with a solution of a polyarylene and a Friedel-Crafts catalyst, said polyarylene having the formula ##STR21## wherein said 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## where said each R 1 is independently a C 1 to C 8 aliphatic radical and p is an integer of 0 to 4, each said 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 and n is an integer of from about 75 to about 10,000; adding to said reaction vessel a pendant forming group G, wherein G is derived from a compound selected from the group consisting of sulfonyl halides having the formula ##STR23## where X is a halogen and R 2 is a C 1 to C 20 aliphatic or a naphthyl radical; a sulfonamide halide having the formula ##STR24## where R 2 is as above and can be the same or different; alkylhalides having the formula R.sub.3 --X where X is a halogen and R 3 is a C 5 to C 20 aliphatic radical; acylhalides having the formula ##STR25## where X is a halogen and R 4 is a C 5 to C 20 aliphatic or an aryl radical of the formula ##STR26## and where R 1 and p are as described above, phosphorus acid halides having the formula X.sub.q --P--(R.sub.5).sub.3-q where X is a halogen; R 5 is selected from the group consisting of R 4 , O--R 4 and mixtures thereof and q is an integer of from 1 to 3; heating the contents of said reaction vessel to form a substituted polyarylene having the formula ##STR27## where G is present in at least five percent of the polyarylene units and R, A, Y, G and n are as described and, thereafter recovering said substituted polyarylene.
Claim 3
Dependent Claim 30 words
A process for the addition of pendant groups, as set forth in claim 1, wherein said polyarylene and Friedel-Crafts catalyst are dissolved in an organic solvent to form a solution.
Claim 4
Dependent Claim 47 words
A process for the addition of pendant groups, as set forth in claim 2, wherein said step of heating is conducted at a temperature range of from about 0° to about 80° C. and for a period of time of from about four to about 16 hours.
Claim 5
Dependent Claim 25 words
A process for the addition of pendant groups, as set forth in claim 3, wherein Y is oxygen, R is methyl and A is hydrogen.
Claim 6
Dependent Claim 29 words
A process for the addition of pendant groups, as set forth in claim 4, wherein said halogens are selected from the group consisting of F, Cl, Br and I.
Claim 7
Dependent Claim 34 words
A process for the addition of pendant groups, as set forth in claim 5, wherein G is sulfonyl, X of said sulfonyl halide is Cl and R 2 of said sulfonyl halide is hexadecyl.
Claim 8
Dependent Claim 34 words
A process for the addition of pendant groups, as set forth in claim 5, wherein G is sulfonamide, X of said sulfonamide halide is Cl and R 2 of said sulfonamide halide is methyl.
Claim 9
Dependent Claim 18 words
A process for the addition of pendant groups, as set forth in claim 5, wherein G is alkyl.
Claim 10
Dependent Claim 18 words
A process for the addition of pendant groups, as set forth in claim 5, wherein G is acyl.
Claim 11
Dependent Claim 18 words
A process for the addition of pendant groups, as set forth in claim 5, wherein G is phosphonyl.

References Cited (Backward Citations)

US3350844A Cited
US3780496A Cited
US4427419A Cited
US4431793A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1989-06-23 1989-12-23 1990-06-24 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1993-06-23 1993-12-23 1994-06-24 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1997-06-23 1997-12-23 1998-06-24 $7700.00 Window Closed / Lapsed

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