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US4431761A Expired / Lapsed US ⏱️ 0.0 years remaining

Ethynyl and substituted ethynyl-terminated polysulfones

Assignee: National Aeronautics and Space Administration
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Filing: 1982-10-08
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Granted: 1984-02-14
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Expires: 2002-10-08
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Abstract

Abstract Ethynyl and substituted ethynyl-terminated polysulfones and a process for preparing the same are disclosed. These polysulfones are thermally cured to induce cross-linking and chain extension, producing a polymer system with improved solvent resistance and use temperatures. Also disclosed are substituted 4-ethynylbenzoyl chlorides as precursors to the substitutetd ethynyl-terminated polysulfones and a process for preparing the same.

Inventors

  • 👤 Paul M. Hergenrother

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-05 16:16
CPC Classifications
C; C08; C08L; C08L81/00; C08L81/06; C08G; C08G65/00; C08G65/34; C08G65/48; C08G75/00; C08G75/20; C08L71/00

Claims Analysis

Total Claims: 9
Claim 1
Independent Claim 92 words
The class of ethynyl or substituted ethynyl-terminated polysulfones of the general formula: ##STR6## where PS is a polysulfone with a molecular weight between 1000 and 50,000 g/mole, and X is selected from the group consisting of: Si(CH 3 ) 3 ; H; straight or branched organic radials having 4 to 10 carbon atoms; substituted aromatic groups of the formula: ##STR7## where R is selected from the group consisting of: straight or branched organic radicals having from 1 to 12 carbon atoms, H, and ##STR8## and halogenated derivatives of all of the above.
Claim 2
Dependent Claim 92 words
The class of ethynyl or substituted ethynyl-terminated polysulfones of the general formula: ##STR6## where PS is a polysulfone with a molecular weight between 1000 and 50,000 g/mole, and X is selected from the group consisting of: Si(CH 3 ) 3 ; H; straight or branched organic radials having 4 to 10 carbon atoms; substituted aromatic groups of the formula: ##STR7## where R is selected from the group consisting of: straight or branched organic radicals having from 1 to 12 carbon atoms, H, and ##STR8## and halogenated derivatives of all of the above.
Claim 3
Dependent Claim 12 words
The cross-linked polymer recovered by thermally treating a polysulfone of claim 1.
Claim 4
Dependent Claim 26 words
The polymer of claim 2 wherein the thermal treatment consists of heating to temperatures from 150°-400° C. for times ranging from 5 minutes to 4 hours.
Claim 5
Dependent Claim 116 words
A process for preparing ethynyl and substituted ethynyl-terminated polysulfones comprised of: disolving a polysulfone, having a molecular weight between 1000 and 50,000 g/mole, in a mixture of chlorinated organic solvent and an organic base, adding dropwise with stirring a solution of 4-bromobenzoyl chloride in a chlorinated organic solvent at temperatures ranging from 10°-50° C., and allowing this mixture to stir 3 hours, precipitating the 4-bromobenzoyl-terminated polymer with a non-solvent, drying the precipitate, and dissolving it in a highly polar solvent, adding an organic base, dichlorobis(triphenylphosphine)palladium, and a substituted acetylene under an inert atmosphere, stirring the mixture for 0.5 to 4 hours at 50°-100° C., and precipitating the resulting substituted ethynyl-terminated polymer with cold dilute aqueous acid.
Claim 6
Dependent Claim 116 words
A process for preparing ethynyl and substituted ethynyl-terminated polysulfones comprised of: disolving a polysulfone, having a molecular weight between 1000 and 50,000 g/mole, in a mixture of chlorinated organic solvent and an organic base, adding dropwise with stirring a solution of 4-bromobenzoyl chloride in a chlorinated organic solvent at temperatures ranging from 10°-50° C., and allowing this mixture to stir 3 hours, precipitating the 4-bromobenzoyl-terminated polymer with a non-solvent, drying the precipitate, and dissolving it in a highly polar solvent, adding an organic base, dichlorobis(triphenylphosphine)palladium, and a substituted acetylene under an inert atmosphere, stirring the mixture for 0.5 to 4 hours at 50°-100° C., and precipitating the resulting substituted ethynyl-terminated polymer with cold dilute aqueous acid.
Claim 7
Dependent Claim 78 words
The process of claim 4 wherein the substituted acetylene is of the formula HC.tbd.C--X, where X is selected from the group consisting of: Si(CH 3 ) 3 ; straight or branched organic radical having 4 to 10 carbon atoms; substituted aromatic groups of the formula: ##STR9## where R is selected from the group consisting of: straight or branched organic radicals having from 1 to 12 carbon atoms, H, and ##STR10## and halogenated derivatives of all of the above.
Claim 8
Dependent Claim 126 words
A process for preparing ethynyl and substituted ethynyl-terminated polysulfones comprising dissolving a polysulfone, having a molecular weight between 1000 and 50,000 g/mole, in a mixture of a chlorinated organic solvent and an organic base, adding a substituted 4-ethynylbenzoyl chloride of the formula: ##STR11## stirring for 0.5 to 4 hours and quenching in a non-solvent to precipitate the resulting substituted ethynyl-terminated polysulfone; where Z is selected from the group consisting of: Si(CH 3 ) 3 ; H; straight or branched organic radicals having from 1 to 10 carbon atoms; substituted aromatic groups of the formula: ##STR12## where R is selected from the group including: straight or branched organic radicals having from 1 to 12 carbon atoms, H, and ##STR13## and halogenated derivatives of all of the above.
Claim 9
Dependent Claim 126 words
A process for preparing ethynyl and substituted ethynyl-terminated polysulfones comprising dissolving a polysulfone, having a molecular weight between 1000 and 50,000 g/mole, in a mixture of a chlorinated organic solvent and an organic base, adding a substituted 4-ethynylbenzoyl chloride of the formula: ##STR11## stirring for 0.5 to 4 hours and quenching in a non-solvent to precipitate the resulting substituted ethynyl-terminated polysulfone; where Z is selected from the group consisting of: Si(CH 3 ) 3 ; H; straight or branched organic radicals having from 1 to 10 carbon atoms; substituted aromatic groups of the formula: ##STR12## where R is selected from the group including: straight or branched organic radicals having from 1 to 12 carbon atoms, H, and ##STR13## and halogenated derivatives of all of the above.

References Cited (Backward Citations)

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US3539657A Cited
US3654192A Cited
US3748306A Cited
US4108926A Cited
US4229560A Cited
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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) 1987-02-13 1987-08-15 1988-02-14 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1991-02-13 1991-08-15 1992-02-14 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1995-02-13 1995-08-15 1996-02-14 $7700.00 Window Closed / Lapsed

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