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Patent US6150426 - Compositions containing particles of highly fluorinated ion exchange polymer - Google PatentsSearch Images Maps Play YouTube News Gmail Drive More »Sign inPatentsSolid and liquid compositions containing particles of highly fluorinated ion-exchange polymer having sulfonate functional groups with an ion exchange ratio of less than about 33. The compositions contain at least about 25% by weight of polymer particles having a particle size of about 2 nm to about 30...http://www.google.com/patents/US6150426?utm_source=gb-gplus-sharePatent US6150426 - Compositions containing particles of highly fluorinated ion exchange polymerAdvanced Patent SearchTry the new Google Patents, with machine-classified Google Scholar results, and Japanese and South Korean patents.Publication numberUS6150426 APublication typeGrantApplication numberUS 08/950,457Publication dateNov 21, 2000Filing dateOct 15, 1997Priority dateOct 15, 1996Fee statusPaidAlso published asCA2268629A1, CN1233267A, DE69705854D1, DE69705854T2, EP0932646A1, EP0932646B1, US6552093, US6916853, US7166685, US7714028, US7893118, US20030176515, US20050119357, US20050171220, US20080227875, US20100174003, WO1998016581A1Publication number08950457, 950457, US 6150426 A, US 6150426A, US-A-6150426, US6150426 A, US6150426AInventorsDennis Edward Curtin, Edward George Howard, Jr.Original AssigneeE. I. Du Pont De Nemours And CompanyExport CitationBiBTeX, EndNote, RefManPatent Citations (24), Non-Patent Citations (4), Referenced by (171), Classifications (19), Legal Events (6) External Links: USPTO, USPTO Assignment, EspacenetCompositions containing particles of highly fluorinated ion exchange polymer
1. A process for preparing an aqueous liquid composition comprising particles of a highly fluorinated ion-exchange polymer having sulfonate functional groups with an ion exchange ratio of less than about 33, said process comprising contacting in a pressurized vessel said polymer with an aqueous liquid dispersion medium under conditions which cause the polymer to form particles, at least about 25% by weight of said particles having a particle size of about 2 nm to about 30 nm, said dispersion medium being substantially free of water miscible organic compounds, cooling the contents of said vessel to a temperature of less than about 100° C., and recovering an aqueous liquid composition comprising particles of said highly fluorinated ion-exchange polymer.
2. The process of claim 1 wherein said contacting is performed in a dispersion medium at a temperature of about 150° C. to about 350° C., the contents of said vessel being agitated sufficiently to subject said contents of said vessel to a shear rate of at least about 150 sec-1.
9. The process of claim 2 wherein said contacting with said dispersion medium is performed at a temperature of about 220 to about 300° C.
12. A process for preparing an aqueous liquid composition comprising particles of a highly fluorinated ion-exchange polymer having sulfonate functional groups with an ion exchange ratio of less than about 33, said process comprising contacting in a pressurized vessel said polymer with an aqueous liquid dispersion medium under conditions which cause the polymer to form particles, at least about 25% by weight of said particles having a particle size of about 2 nm to about 30 nm, cooling the contents of said vessel to a temperature of less than about 100° C., and recovering an aqueous liquid composition comprising particles of said highly fluorinated ion-exchange polymer, said dispersion medium comprising 0.5 to 75% by weight of a dispersion assist additive selected from the group consisting of nonreactive, substantially water immiscible organic compounds and carbon dioxide.
14. A process for preparing an aqueous liquid composition comprising particles of a highly fluorinated ion-exchange polymer having sulfonate functional groups with an ion exchange ratio of less than about 33, said process comprising contacting in a pressurized vessel said polymer with an aqueous liquid dispersion medium under conditions which cause the polymer to form particles, at least about 25% by weight of said particles having a particle size of about 2 nm to about 30 nm, cooling the contents of said vessel to a temperature of less than about 100° C., and recovering an aqueous liquid composition comprising particles of said highly fluorinated ion-exchange polymer, said process further comprising removing liquid components of said aqueous liquid composition to produce a solid composition.
16. A process for preparing an aqueous liquid composition comprising particles of a highly fluorinated ion-exchange polymer having sulfonate functional groups with an ion exchange ratio of less than about 33, said process comprising contacting in a pressurized vessel said polymer with an aqueous liquid dispersion medium under conditions which cause the polymer to form particles, at least about 25% by weight of said particles having a particle size of about 2 nm to about 30 nm, cooling the contents of said vessel to a temperature of less than about 100° C., and recovering an aqueous liquid composition comprising particles of said highly fluorinated ion-exchange polymer, said process further comprising contacting the recovered liquid composition with H2 O2.
The invention also provides a process for preparing an aqueous liquid composition comprising particles of highly fluorinated ion-exchange polymer having sulfonate functional groups and having an ion exchange ratio of less than about 33. The process includes contacting the polymer in a pressurized vessel with an aqueous liquid dispersion medium under conditions which cause the polymer to form particles with at least about 25% by weight of said particles having a particle size of about 2 nm to about 30 nm. The contents of the vessel is cooled to a temperature of less than about 100° C. and an aqueous liquid composition comprising particles of the highly fluorinated ion-exchange polymer is recovered. Preferably, the dispersion medium for use in the process is substantially free of water miscible alcohols, the temperature is about 150° C. to about 300° C., and the contents of the vessel is agitated sufficiently to subject the contents of the vessel to a shear rate of at least about 150 sec-1.
The SAXS patterns of compositions in accordance with the invention show a sharp peak that shifts to lower q (or scattering angle) upon dilution. This suggests that the peak can be attributed to the nature of inter-particle interference. Thus, an averaged inter-particle distance (d) can be estimated from the peak position, q.sub.(max), in the plots of I·q2, following Bragg's Law:
In I·q2 plots, one can also see a secondary peak, which is located at about 0.2q.sub.(max), for compositions in accordance with the invention. The SAXS patterns suggest the presence of a large amount of particles of averaged particle size of less than 11.4 nm which are arranged in a fairly ordered fashion to rise to the sharp SAXS peaks and secondary peaks. The liquid composition made as in U.S. Pat. No. 4,433,082 have a very different pattern with only a shoulder in the range of q where the invention shows the strong peak. Assuming that this shoulder is a result of inter-particle interference as in the compositions of the invention, the compositions of the invention clearly have a much higher percentage of particles in the particle size range of about 2 nm to 30 nm.
A process for preparing compositions in accordance with the invention comprises contacting the highly fluorinated ion exchange polymer in a pressurized vessel with an aqueous liquid dispersion medium under conditions which cause the polymer to form particles with at least about 25% by weight of said particles having a particle size of about 2 nm to about 30 nm. Preferably, the temperature employed is about 1 50° C. to about 350° C. Most preferably, a temperature of about 220 to about 300° C. is used.
With reference to the organic compound dispersion assist additives, "substantially water immiscible" is intended to mean that the solubility of the compound in water at 25° C. is less than 0.2% by weight. These compounds provide improved dispersion properties to the aqueous medium but are readily separated from the liquid product after processing.
In a preferred form of the process, the recovered liquid composition is contacted with H2 O2 for the purposes of decreasing odor and/or color. The compositions sometimes are contaminated with sulfur containing impurities because dimethyl sulfoxide is sometimes used to swell the polymer during hydrolysis to increase the reaction rate and the odor is believed to be due to sulfur containing impurities. Preferably, the recovered liquid composition is heated while it is contacted with H2 O2, most preferably to about 90-100° C.
Coalescence temperatures vary with polymer composition. A typical coalescence temperature for a TFE/PDMOF (--SO3 H) (IXR 14.7) (EW1080) copolymer is approximately 175° C. With the same polymer with an IXR of 23 (EW of 1500), the coalescence temperature is somewhat higher, i.e., approximately 225° C. With a TFE/POPF (--SO3 H) (IXR 12) (EW778) copolymer, the coalescence temperature is somewhat higher at the low IXR (low EW) values, i.e., approximately 225° C. Preferably, liquid components are removed from the composition by heating to a temperature of less than about 100C. Freeze-drying is another preferred method to remove the liquid components since it produces a friable solid material which may be handled and redispersed particularly easily. Spray drying at a temperature less that the coalescence temperature is also effective for making redispersible powdered compositions.
A 400 ml shaker tube made of an acid resistant alloy sold under the trademark HASTELLOY® C-276 by the Haynes Company is charged with 200 ml of water, 50 ml of benzene, and 25 g of a TFE/PDMOF copolymer having an IXR of 14.7 (EW of 1080). The TFE/PDMOF copolymer is in bead form with the --SO2 F groups of the copolymer having been hydrolyzed and acid exchanged to the --SO3 H form. The copolymer contains 13% by weight of absorbed water.
TABLE 1______________________________________Part  TFE/PDMOF g            IXR     EW   Org. Cmpd.                                  % Solids______________________________________1     67         14.7    1080 Benzene  22.7  2 100  14.7 1080 Benzene 32.2a  3 35 23 1500 Benzene 6.8  4 50 23 1500 Benzene 13.2b  5 25 14.7 1080 FC-75c 8.3  6 25 14.7 1080 Toluene 10.0  7 25 14.7 1080 Cyclohexane 9.3  8 25 14.7 1080 Naphthalene 17.0  9 25 14.7 1080 Fluorobenzene 14.3  10 25 14.7 1080 n-Heptane 8.0  11 25 14.7 1080 Benzene 7.0d  12 43.6e    14.7 1080 Benzene 23.0  14  60d 14.7 1080 Biphenyl 16.1______________________________________ a = forms paste b = 12 hour time c = FC75 is perfluoro butyl tetrahydrafurane d = Ran at 170° C. e = Hydrolyzed TFE/PDMOF copolymer is in the form of hot waterwashed film
Two liquid compositions are made using the same conditions, 5 hours at 230° C., but one example is carried out in a shaker tube of the type used in Example 1 and the other in a stirred autoclave. It is estimated that the stirred autoclave provides a shear rate of approximately 15,000 sec-1 The shaker tube provides substantially less shear, i.e., shear rate of approximately 160 sec-1. Each Part described below used excess TFE/PDMOF (--SO3 H form) (IXR 14.7 or 14.5) (EW1080 or 1070) so that some unchanged material remains in each after 5 hours.
Liquid compositions are made as in Example 4, Part 2, except that 800 g TFE/PDMOF (--SO3 H form) (IXR 14.7) (EW1070) and 2500 ml water are used and the composition is formed at 255° C. for 2 hours. The liquid composition contains 23.5% solids. No solid TFE/PDMOF remains in the vessel.
A liquid composition is made in a shaker tube of the same type as used in Example 1 using 70 g TFE/POPF (--SO3 H form) (IXR 12) (EW 778), 100 ml H2 O and 30 ml benzene and heated at 230° C. for 5 hours with shaking. The vessel was not shaken during the cooling. The clear liquid product contains 33.1% solids and had a viscosity approximating that of ethylene glycol. Compared to TFE/PDMOF (--SO3 H form) (IXR 14.7) (EW 1080), this viscosity is extremely low for this concentration.
A film is cast from 10% by weight solids dispersion of TFE/PDMOF (--SO3 H form) (IXR 14.5) (EW1070) in dimethylformamide onto a glass slide at room temperature. The film is exposed to the air until dry and then is heated to 65° C. for 5 minutes. The resulting film is colorless, transparent and smooth. The procedure is repeated with a 10% by weight solids dispersion TFE/PDMOF (IXR 14.5) (EW1070) in N-methyl pyrrolidone to produce a similar film.
A TFE/PDMOF(--SO3 H) liquid composition is prepared by the method described in Grot, U.S. Pat. No. 4,433,082. A 250 gallon HASTELLOY® (Haynes Company) tank, fitted with a two-stage prop-style agitator and oil-heated jacket, is filled with a liquid medium containing 209 kg of de-ionized water, 91 kg of 1-propanol and 43 kg of methanol, plus 32 kg of TFE/PDMOF(--SO3 H) (IXR 14.5) (EW1070) in bead form. This mixture is heated to a temperature of 232° C., then held at that condition for a period of 3 hours. After cooling to a temperature below 30° C. and venting ether vapors, some solid material remains in the vessel which is removed when the solution is passed through a filter. The product composition produced by this process contains approximately 9% by weight of TFE/PDMOF(--SO3 H) (IXR 14.5) (EW1070), which is diluted to approximately 5% by weight using water, 1-propanol and 2-propanol.
The above-described 5% by weight TFE/PDMOF (--SO3 H form) liquid composition is concentrated to 14% solids by vacuum distillation at 58° C. By using this vacuum distillation procedure, substantially all of the alcohols present in the composition are removed with the distillate. Upon cooling to room temperature, the concentrate set to a gel. When a sample of the gel is added to water, a fluid liquid composition again results indicating that conversion to a gel does not disastrously alter the particle structure in the composition.
A shaker tube is charged with 60 g TFE/PDMOF (--SO3 H form) (IXR 14.7) (EW1080) as beads and 250 ml H2 O. After sealing the vessel, 40 g CO2 is pumped in. The vessel was shaken at 230° C. for 5 hours at autogenous pressure (approx. 4300 psi-29600 kPa). The shaking is stopped and the vessel is cooled to room temperature. The gas is vented through a tube into a catch pan to collect the product that formed. The material remaining in the vessel is combined with that in the catch pan and placed in a separatory funnel to remove a small amount of white foam. No solid polymer remains in the vessel. The colorless and clear liquid composition contains 22.0% solids.
Sample 1--TFE/PDMOF (IXR 14.5) (EW 1070) composition prepared as in Example 4, Part 2, i.e., prepared in water at 230° C. for 5 hours except also containing benzene.
Sample 2--TFE/PDMOF (IXR 14.5) (EW 1070) composition of Example 5, i.e., prepared in water only at 255° C. for 2 hours.
Sample 3--TFE/PDMOF (IXR 23) (EW 1500) composition prepared as in Example 2, Part 3, i.e, prepared in water with benzene at 230° C. for 5 hours.
Sample 4--TFE/POPF (IXR 12) (EW 778) composition prepared as in Example 6, i.e., prepared in water with benzene at 230° C. for 5 hours (60 g polymer, 200 ml water, 50 ml benzene, 20% solids).
TABLE 3______________________________________Stability of Films in 100° C. H2 O  Coalescence     SampleTemp. ° C.         1     2           3   4______________________________________150           -     -           -   -  175 + + - -  200 + + - +  225   + +______________________________________
A 26.2% solids colloid is made according to the procedure of Example 1, Part 1, except that it is made in a stirred autoclave using 780 g TFE/PDMOF (--SO3 H) (IXR 14.5) (EW1070) film, 2 l water, and 500 ml benzene. The colloid is applied to the top surface of a fired but not glazed porous ceramic plate measuring 51/4"×51/4"×0.31" (13.3 cm×13.3 cm×0.79 cm). The colloid penetrates into the top surface of the plate and forms a film when dried at room temperature. The film formed is tested for gas tightness by flooding the top of the plate, i.e., the TFE/PDMOF film side, with n-heptane and contacting the underside with the open end of a rubber tube supplying N2 at 7 inches H2 O (1.7 kPa) pressure on under side of the plate. No bubbles form in the heptane.
In one hour, the control DRIERITE® turns lavender color caused by the presence of both pink and blue CoCl. The DRIERITE® inside the dome turns lavender in 20 minutes and completely pink in 11/2 hours indicating transport of vapor across the plate coated with TFE/PDMOF. After 5 hours, the control is still lavender in color.
To 10 g of the TFE/PDMOF (--SO3 H form) colloid (21% solids) prepared as in Example 4, Part 2, is added 0.03 g of the surfactant n-C7 F15 CO2 --NH4 + sold under the trademark FC-143 by 3M, of Minneapolis, Minn. dissolved in 1 ml H2 O. This gives a clear fluid liquid which wet a PTFE fiber bundle sold under the trademark TEFLON® by the DuPont Company (400-60-0 Merge IT O13 6.7 DPF Lot 12272). The fiber is soaked in the colloid for 15 minutes. After shaking off the excess liquid, the fiber is dried and then heated to 200° C. for a few seconds to coalesce the TFE/PDMOF. The bundle of fibers is now stiff and obviously coated.
Aqueous Perfloroalkoxy Dispersion--(Teflon® 335--DuPont) Product: Thick, but pours.
Aqueous PTFE Dispersion--(Teflon® 3170--DuPont) Product: Thick, but pours
Aqueous Fluorinated Ethylene Propylene Dispersion--(Teflon® 1201--DuPont)
TABLE 5__________________________________________________________________________    Age           H2 O                Benzene                      Time                         Temp.                              Solids  Sample mo. IXR EW (g) ml ml hrs. ° C. Content__________________________________________________________________________1   5.5 14.7      1080 (25)             200 50   5  230  10  2 5.5 14.7 1080 (20) 200 0 5 230 6.6  3 5 23 1500 (30) 200 50 5 230 8.0  4 5 14.7  1080 (436) 200 50 5 230 23.0  5 3.5 14.5  1070 (600) 2000 0 5 230 15.8__________________________________________________________________________
The amount of 1500 EW polymer in the clear liquid relative to the amount charged is used to determine the solution yield. The "Wt % Goal" column in the Table assumes that all 100% of charged polymer is dispersed. This example illustrates that the solution yield as a percentage of the polymer charged is a function of the temperature of the run and not of the amount charged or length of time at temperature. At 260° C. (Parts 2 to 5), about 48% is dispersed into the clear liquid phase and the rest is recovered as undispersed pellets no matter what the dilution or heating time. At 300° C. (Parts 6 to 8) all polymer goes into the liquid phase. Furthermore the insoluble fraction of pellets recovered from Parts 2 to 5 at 260° C. are dispersed fully into the liquid phase at 300° C. (Part 8) and no insoluble pellets remain.
TABLE 6______________________________________Wt %   Shaker Tube                 Time Weight %                             Solution  Part Goal Temperature (hr) Solution Yield Comments______________________________________1*   14.9   230° C.                 5    6.8    45.7% Example 2,   Part 3  2 16.7 260° C. 5 8.4% 50.4% Pellets remain  3 9.1 260° C. 5 4.0 44% Pellets remain  4 9.1 260° C. 24 4.4 48.4% Pellets remain  5 13.0 260° C. 8 6.5 49.8% Pellets remain  6 9.1 300° C. 5 9.0 98.9% Clear liquid  7 15.0 300° C. 5 14.6 97.3 Pellets gone  8 9.1 300° C. 5 6.7 87.9 Insolubles   from 260° C.   runs______________________________________ *Example 2, Part 3 repeated here (contains benzene).
To 100 grams of the liquid composition made by the procedure of Example 5 (14.5 IXR--1070 EW polymer containing 0.026 equivalents --SO3 H groups) and 20 milliliters of water is added with stirring over 7 minutes a solution of 0.62 grams (0.026 equivalents) of lithium hydroxide in 20 milliliters of water. The resulting clear liquid contains 24.6% solids. The solution remains clear, is very light amber in color, has a moderate viscosity and is free flowing for months. It is readily cast on KAPTON® polyimide film (DuPont Company) and cured at 225° C. to give a clear colorless coating which can be peeled off as smooth strong clear films. The cast films of lithium salt (--SO3 Li) of 1070 EW polymer are particularly good at remaining light colored after high temperature cures compared with the proton form (--SO3 H).
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Du Pont De Nemours And CompanyIonomer composite membranes, methods for making and using* Cited by examinerClassifications U.S. Classification521/28, 524/167, 524/755International ClassificationC08J3/09, B01J39/16, C08J3/03, C08J7/04, C08L27/18, C08J3/16, D01F6/32, C08J5/18Cooperative ClassificationC08J2327/18, D01F6/32, C08J5/18, C08J2327/12, C08J3/16European ClassificationC08J5/18, C08J3/16, D01F6/32Legal EventsDateCodeEventDescriptionFeb 26, 1998ASAssignmentOwner name: E. I. DU PONT DE NEMOURS AND COMPANY, DELAWAREFree format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:CURTIN, DENNIS EDWARD;HOWARD, EDWARD GEORGE, JR.;REEL/FRAME:009059/0052;SIGNING DATES FROM 19980216 TO 19980217Apr 14, 2004FPAYFee paymentYear of fee payment: 4May 9, 2008FPAYFee paymentYear of fee payment: 8Apr 25, 2012FPAYFee paymentYear of fee payment: 12Apr 15, 2015ASAssignmentOwner name: THE CHEMOURS COMPANY FC, LLC, DELAWAREFree format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:E. I. DU PONT DE NEMOURS AND COMPANY;REEL/FRAME:035432/0023Effective date: 20150414Jun 10, 2015ASAssignmentOwner name: JPMORGAN CHASE BANK, N.A., NEW YORKFree format text: SECURITY AGREEMENT;ASSIGNORS:THE CHEMOURS COMPANY FC LLC;THE CHEMOURS COMPANY TT, LLC;REEL/FRAME:035839/0675Effective date: 20150512RotateOriginal ImageGoogle Home - Sitemap - USPTO Bulk Downloads - Privacy Policy - Terms of Service - About Google Patents - Send FeedbackData provided by IFI CLAIMS Patent Services