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US4209554A Expired / Lapsed US ⏱️ 0.0 years remaining

Polydentate metal salts used in the process for the deactivation of glass surfaces and capillary columns therewith

Assignee: SCM Glidco Organics Corp
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Filing: 1979-02-22
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Granted: 1980-06-24
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Expires: 1999-02-22
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Abstract

Abstract Phosphonium salts are prepared by reacting polydentate phosphines containing two or more trivalent phosphorus atoms with alkyl or aralkyl halides. Treatment of glass surfaces and glass capillary columns with these salts substantially eliminates tailing of peaks and allow the high temperature separation and characterization of polar compounds by gas chromatography at temperatures of 300° C.

Inventors

  • 👤 Sean G. Traynor
  • 👤 George Marcelin

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-01 13:57
CPC Classifications
B; B01; B01D; B01D53/00; B01D53/02; B01D53/025; C; C03; C03C; C03C17/00; C03C17/28; C07; C07F; C07F9/00; C07F9/02; C07F9/28; C07F9/54; C07F9/5449

Claims Analysis

Total Claims: 10
Claim 1
Independent Claim 281 words
A process for deactivating glass capillary columns which comprises treating the internal surfaces of a capillary column with one or more deactivating polydentate salts either prior to or in conjunction with the application of liquid substrate capable of separating complex mixtures of compounds using gas chromatographic techniques wherein the said columns are operated up to 300° C. and above and wherein the salts comprise the reaction product of (a) a polydentate compound containing two or more quaternizable group V-A elements of the following formula: (1) R 1 R 2 MAMR 1 R 2 ; (2) (R 1 R 2 MA) 3 M; (3) (R 1 R 2 MA) 2 MR 3 ; (4) (R 1 R 2 MA) 2 MAM(AMR 1 R 2 ) 2 ; and ##STR2## wherein M is independently a group V-A element selected from the group consisting of phosphorus, antimony and arsenic; R 1 , R 2 and R 3 are the same or different C 1-20 alkyl radical, or an aromatic radical containing up to twelve carbon atoms and A represents a straight chain or branched lower alkylene radical containing from 2 to 6 carbons; n is an integer from 1 to 6; and (b) a quaternary salt forming mono or difunctional alkyl or aralkyl halide selected from the group consisting of (1) R 4 X; (2) ArR 5 X; (3) XR 6 X; and (4) XCH 2 MCH 2 X wherein X is halogen; R 4 is an alkyl radical containing 2 to 6 carbon atoms; R 6 is lower alkylene radical containing 2 to 6 carbon atoms; Ar is a mono or divalent aryl radical which may contain one or more halogen ring substituents.
Claim 2
Dependent Claim 281 words
A process for deactivating glass capillary columns which comprises treating the internal surfaces of a capillary column with one or more deactivating polydentate salts either prior to or in conjunction with the application of liquid substrate capable of separating complex mixtures of compounds using gas chromatographic techniques wherein the said columns are operated up to 300° C. and above and wherein the salts comprise the reaction product of (a) a polydentate compound containing two or more quaternizable group V-A elements of the following formula: (1) R 1 R 2 MAMR 1 R 2 ; (2) (R 1 R 2 MA) 3 M; (3) (R 1 R 2 MA) 2 MR 3 ; (4) (R 1 R 2 MA) 2 MAM(AMR 1 R 2 ) 2 ; and ##STR2## wherein M is independently a group V-A element selected from the group consisting of phosphorus, antimony and arsenic; R 1 , R 2 and R 3 are the same or different C 1-20 alkyl radical, or an aromatic radical containing up to twelve carbon atoms and A represents a straight chain or branched lower alkylene radical containing from 2 to 6 carbons; n is an integer from 1 to 6; and (b) a quaternary salt forming mono or difunctional alkyl or aralkyl halide selected from the group consisting of (1) R 4 X; (2) ArR 5 X; (3) XR 6 X; and (4) XCH 2 MCH 2 X wherein X is halogen; R 4 is an alkyl radical containing 2 to 6 carbon atoms; R 6 is lower alkylene radical containing 2 to 6 carbon atoms; Ar is a mono or divalent aryl radical which may contain one or more halogen ring substituents.
Claim 3
Dependent Claim 29 words
The process of claim 1 wherein the polydentate salt is prepared from a phosphine selected from the group consisting of (a) 1,1,4,4-tetraphenyl 1,4-diphosphabutane; (b) tris(2-diphenylphosphinoethyl)phosphine; (c) 1,1,4,7,7-pentaphenyl-1,4,7-triphosphaheptane; (d) 1,1,4,7,10,10-hexaphenyl-1,4,7,10-tetraphosphadecane.
Claim 4
Dependent Claim 15 words
The process of claim 1 wherein the said phosphines are substantially completely quaternized with benzylbromide.
Claim 5
Dependent Claim 13 words
The process of claim 1 wherein the said phosphine is quaternized with 1,4-dibromobutane.
Claim 6
Dependent Claim 13 words
The process of claim 1 wherein the said phosphine is quaternized with α,α'-dibromo-p-xylene.
Claim 7
Dependent Claim 10 words
The process of claim 3 wherein the phosphine is 1,1,4,7,7-pentaphenyl-1,4,7-triphosphaheptane.
Claim 8
Dependent Claim 10 words
The process of claim 3 wherein the phosphine is 1,1,4,7,10,10-hexaphenyl-1,4,7,10-tetraphosphadecane.
Claim 9
Dependent Claim 154 words
A process for preparing glass capillary columns useful in analyzing complex mixtures of compounds by gas chromatographic techniques at operating temperatures up to 300° C. and above which comprises (a) pretreating the internal surfaces of a capillary column with one or more hydrogen halides at column temperatures in the range of 300° C. to 450° C. for 1 to 4 hours; (b) cooling the treated column under a nitrogen purge to room temperature; (c) under a positive inert gas pressure treating the column with a solution of one or more surface deactivating polydentate salts prepared from polydentate phosphines containing two or more trivalent phosphorus atoms or their antimony or arsenic analogs; (d) drying the column under an inert atmosphere; (e) coating the cooled column with a liquid substrate useful in separating complex mixtures of organic compounds; and (f) conditioning the coated column at temperatures up to the maximum operating temperature of the chromatographic substrate.
Claim 10
Dependent Claim 154 words
A process for preparing glass capillary columns useful in analyzing complex mixtures of compounds by gas chromatographic techniques at operating temperatures up to 300° C. and above which comprises (a) pretreating the internal surfaces of a capillary column with one or more hydrogen halides at column temperatures in the range of 300° C. to 450° C. for 1 to 4 hours; (b) cooling the treated column under a nitrogen purge to room temperature; (c) under a positive inert gas pressure treating the column with a solution of one or more surface deactivating polydentate salts prepared from polydentate phosphines containing two or more trivalent phosphorus atoms or their antimony or arsenic analogs; (d) drying the column under an inert atmosphere; (e) coating the cooled column with a liquid substrate useful in separating complex mixtures of organic compounds; and (f) conditioning the coated column at temperatures up to the maximum operating temperature of the chromatographic substrate.

References Cited (Backward Citations)

US3488922A Cited
US3722181A Cited
US4054432A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1983-06-24 1983-12-24 1984-06-24 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1987-06-24 1987-12-24 1988-06-24 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1991-06-24 1991-12-24 1992-06-24 $7700.00 Window Closed / Lapsed

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