WO1999038897A1 - Polymeres sulfones reticules et leur procede de preparation - Google Patents
Polymeres sulfones reticules et leur procede de preparation Download PDFInfo
- Publication number
- WO1999038897A1 WO1999038897A1 PCT/CA1999/000078 CA9900078W WO9938897A1 WO 1999038897 A1 WO1999038897 A1 WO 1999038897A1 CA 9900078 W CA9900078 W CA 9900078W WO 9938897 A1 WO9938897 A1 WO 9938897A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- polymer
- crosslinking
- radicals
- organic
- optionally
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/20—Manufacture of shaped structures of ion-exchange resins
- C08J5/22—Films, membranes or diaphragms
- C08J5/2206—Films, membranes or diaphragms based on organic and/or inorganic macromolecular compounds
- C08J5/2218—Synthetic macromolecular compounds
- C08J5/2231—Synthetic macromolecular compounds based on macromolecular compounds obtained by reactions involving unsaturated carbon-to-carbon bonds
- C08J5/2243—Synthetic macromolecular compounds based on macromolecular compounds obtained by reactions involving unsaturated carbon-to-carbon bonds obtained by introduction of active groups capable of ion-exchange into compounds of the type C08J5/2231
- C08J5/225—Synthetic macromolecular compounds based on macromolecular compounds obtained by reactions involving unsaturated carbon-to-carbon bonds obtained by introduction of active groups capable of ion-exchange into compounds of the type C08J5/2231 containing fluorine
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F214/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
- C08F214/18—Monomers containing fluorine
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/44—Preparation of metal salts or ammonium salts
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/20—Manufacture of shaped structures of ion-exchange resins
- C08J5/22—Films, membranes or diaphragms
- C08J5/2206—Films, membranes or diaphragms based on organic and/or inorganic macromolecular compounds
- C08J5/2218—Synthetic macromolecular compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2327/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers
- C08J2327/02—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers not modified by chemical after-treatment
- C08J2327/12—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms
Definitions
- the present invention relates to ion exchange resins of the type
- cationic, in particular in membrane form preferably partially or
- electrochemicals such as fuel cells, chlorine-soda processes,
- FC CF ⁇ O-CF ) CF-O ' • (CF 2 t-C0 2 CH 3
- X is F, Cl or CF 3 ;
- - n is 0 to 10 inclusive
- Aromatic polymers of the polyimide or polyether sulfone sulfone type have
- sulfonate and carboxylate includes proton, cation of an alkali metal (Li + , Na + , K + );
- onium type, such as oxonium, ammonium, pyridinium, guanidinium, amidinium,
- organometallic cation such as metallocenium
- the membrane does not have good dimensional stability and swells so
- TFE Tetrafluoroethylene
- the perfluorocarbon portion of the polymer allows easy diffusion of the species
- Faradaic efficiency mainly in methanol fuel cells.
- Non-fluorinated systems such as sulfonated polyimides or polyethers
- the present invention relates to a sulfone polymer comprising a fraction
- crosslinking bonds carry an ionic charge. More specifically, the links of
- crosslinking are of the type:
- - Y includes N or CR in which R comprises H, CN, F, SO 2 R 3 , C ] _ 20 substituted alkyl
- R 3 includes F, C 2Q substituted or unsubstituted alkyl; C ⁇ o aryl substituted or not
- M + comprises an inorganic or organic cation
- Q comprises a divalent radical C ⁇ alkyl, C ⁇ o oxaalkyle, C, _ 20 azaalkyle, C ⁇
- halogens by one or more halogens, and in which the chain comprises one or more
- r is 0 or 1.
- M + comprises the proton, the cation of a
- alkyl alkenyl, oxaalkyl, oxaalkenyl, azaalkyl radicals
- heteroatoms such as nitrogen, oxygen or sulfur
- the metal preferably comprises an alkali metal, an alkali metal
- the organometallic cation includes a
- metallocenium an arene-metallocenium, an alkylsilyl, an alkylgermanyl or a
- alkyltin and the organic cation comprises a group R "O + (onium), NR" + (ammo ⁇
- organic contains at least two R "radicals different from H, these radicals can be
- the present invention further comprises a method of crosslinking
- crosslinking bonds carry an ionic charge
- crosslinking bonds The preferred crosslinking agents have the formula:
- crosslinks i.e., links, between the sulfonyl groups attached to
- adjacent polymer chains including those with a perfluorinated backbone, for example,
- FC CF- 0- CF 2 -CF- ( CF 2 -CF -SO, FI
- the crosslinking can be carried out while the polymer - 8 -
- the present invention also relates to the molding of the crosslinked polymer in the form
- membranes for use in a pile
- polymer chain is also part of the invention.
- R - A includes M, Si (R ') 3 , Ge (R') 3 or Sn (R ') 3 in which R' is C ,. lg alkyl;
- - L comprises a labile group such as a halogen (F, Cl, Br), a heterocycle
- the cation M + can itself be solvated or complexed to increase its
- solubility and / or its reactivity For example, if M is a proton, the latter can be
- a tertiary base having a strong nucleophilic character such as
- cross-linking agent A 2 Y " (M + ) can be formed in situ by
- a strong base for example an organometallic or an amino dialkyl
- organometallic crosslinking agents include organo-
- crosslinking in addition to improving the mechanical properties, has no harmful effect on the
- DABCO 1,4-diazabicyclo- [2,2,2,] - octane. - 11 -
- the crosslinking reaction can take place when the
- group Y is already on the precursor of the polymer, for example in the case of a
- the crosslinking reaction can involve all of the groups
- crosslinking reagents can be any crosslinking reagent that can be used.
- the polymer is molded into the desired form before crosslinking, by
- the preferred solvents are polyhalocarbons,
- THF tetrahydrofuran
- glymes glymes
- tertiary alkylamides such as
- temperatures are chosen as compatible with usual solvents, from -10 ° C to
- a latex of the molding polymer is preferably mixed in
- non-solvent fluids such as ordinary hydrocarbons or
- filling organic or inorganic, such as powders, fibers or filaments
- woven or not can be added to the polymers before the crosslinking reaction to
- halogen organic particularly fluorinated
- crosslinkers such as M [(CH 3 ) 3 SiO], M [(CH 3 ) 3 SiNSO 2 R F ] or M [(CH 3 ) 3 SiC (R) SO 2 R F ], or
- crosslinking agent and the non-crosslinking ionogenic agent are mixed
- the crosslinked polymer obtained according to the process of the present invention can be any crosslinked polymer obtained according to the process of the present invention.
- reaction side products which are either volatile, such as
- crosslinked polymer (CH 3 ) 3 SiF or (CH 3 ) 3 SiCl.
- the crosslinked polymer can be washed using
- a suitable solvent such as water or an organic solvent in which it is insoluble.
- ion exchange or electrophoresis can be used to change the
- chlorosulfonated form in chlorosulfonated form is formed into a film by pressing and calendering at 150 ° C.
- a film 50 microns thick is cut into squares 4 cm wide and immersed in
- DMEU dimethylethyleneuree
- boiling temperature is less than 10%.
- polypropylene are immersed in a glass tank and covered with a solution of
- perfluorovinyloxyethane-sulfonyl of example 3 is treated with a solution of 800 mg
- methanesulfonamide of formula Na [Si (CH 3 ) 3 NSO 2 CF 3 ] in the diglyme at 125 °.
- the polymer is in the form of granules of
- the compound [CF3S ⁇ 2C (MgCl) 2S ⁇ 2CF2] 2CF2 is prepared from the acid fluoride
- reaction sequence is done in the same container ("one pot” synthesis) in ether
- a 4-trifluorovinyl-benzenesulfonyl fluoride polymer is prepared by
- cyclopentanone is spread using a template and the solvent is dried in dry air.
- polymer film obtained has a thickness of 24 microns. 100 cm 2 of this membrane are
- reaction medium (50:50 v / v).
- the reaction medium is maintained at 80 ° C for 10 hours and the sub-
- reaction products are eliminated by successive washings in THF, methanol and
- Example 7 The poly (4-trifluorovinyl-benzenesulfonyl fluoride) of Example 7 is spread in the form
- This assembly is placed in a
- the reactor is closed and kept at 115 ° C for 4 hours under
- FC-75® (3M, USA). The suspension is spread using a template on a strip
- the fluoropolymer is crosslinked by hot pressing at 100 Kg.cm "2 and 150 ° C for 1
- sulfonamide is obtained by treatment with a hydrochloric acid solution and rinsed.
- the sodium salt is obtained by immersion in a 10% solution of carbonate
- the membrane is placed in a reactor containing 100 ml
- the sulfonamide functions -SO 2 NH 2 are treated with a
- An experimental fuel cell is made from a membrane
- the experimental cell is tested with a hydrogen supply
- the open circuit voltage is 1.2 V and the curve
- platinum-ruthenium 50:50 allows the use as methanol fuel with a
- An experimental fuel cell is made from a membrane
- platinum from example 11 is applied on both sides of the membrane by screen printing
- the experimental fuel cell using this assembly has performances
- the electrolysis of sodium chloride is carried out in a cell with two
- DSA type (“dimension stable electrode") and made of titanium covered with a
- the membrane prepared according to Example 4 is used for the preparation
- the cathode is a
- cathodic is immersed in water. Faradic yield of ozone and 20%) under
- methoxyacetophenone is complete in 45 minutes at room temperature.
- the catalyst is removed by simple filtration and reusable.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Fuel Cell (AREA)
Abstract
Description
Claims
Priority Applications (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA2283668A CA2283668C (fr) | 1998-01-30 | 1999-01-29 | Polymeres sulfones reticules et leur procede de preparation |
DE69916715T DE69916715T2 (de) | 1998-01-30 | 1999-01-29 | Vernetzte sulfonierte polymere und verfahren zur herstellung davon |
EP99902478A EP0973809B1 (fr) | 1998-01-30 | 1999-01-29 | Polymeres sulfones reticules et leur procede de preparation |
JP53874999A JP4477149B2 (ja) | 1998-01-30 | 1999-01-29 | 架橋したスルホン化ポリマーおよびその製造法 |
US09/906,702 US20020002240A1 (en) | 1998-01-30 | 2001-07-18 | Cross-linked sulphonated polymers and method for preparing same |
US10/094,047 US6649703B2 (en) | 1998-01-30 | 2002-03-08 | Cross-linked sulphonated polymers and their preparation process |
US10/813,692 US7034082B2 (en) | 1998-01-30 | 2003-05-14 | Cross-linked sulphonated polymers and their preparation process |
US11/380,133 US7674560B2 (en) | 1998-01-30 | 2006-04-25 | Cross-linked sulphonated polymers and their preparation process |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA2,228,467 | 1998-01-30 | ||
CA 2228467 CA2228467A1 (fr) | 1998-01-30 | 1998-01-30 | Nouvelles techniques et nouveaux procedes pour la reticulation de membranes echangeuses d'ions, et applications |
CA 2236197 CA2236197A1 (fr) | 1998-04-28 | 1998-04-28 | Nouvelles techniques et nouveaux procedes pour la reticulation de membranes d'echange ionique et applications connexes |
CA2,236,197 | 1998-04-28 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US09/390,648 Continuation US6670424B1 (en) | 1998-01-30 | 1999-09-07 | Ross-linked sulphonated polymers and their preparation process |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1999038897A1 true WO1999038897A1 (fr) | 1999-08-05 |
Family
ID=25680017
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/CA1999/000078 WO1999038897A1 (fr) | 1998-01-30 | 1999-01-29 | Polymeres sulfones reticules et leur procede de preparation |
Country Status (5)
Country | Link |
---|---|
US (5) | US6670424B1 (fr) |
EP (2) | EP0973809B1 (fr) |
JP (1) | JP4477149B2 (fr) |
DE (2) | DE69916715T2 (fr) |
WO (1) | WO1999038897A1 (fr) |
Cited By (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6090895A (en) * | 1998-05-22 | 2000-07-18 | 3M Innovative Properties Co., | Crosslinked ion conductive membranes |
WO2001027167A1 (fr) * | 1999-10-12 | 2001-04-19 | Millipore Corporation | Compositions polymeres de fluorocarbone possedant des groupes fonctionnels hydrophiles et procede |
JP2001319521A (ja) * | 2000-05-09 | 2001-11-16 | Toyota Central Res & Dev Lab Inc | 電解質の改質方法及び改質電解質 |
WO2001096268A2 (fr) * | 2000-06-13 | 2001-12-20 | HYDRO-QUéBEC | ÉLASTOMÈRES RÉTICULABLES FLUORÉS BROMOSULFONÉS À BASE DE FLUORURE DE VINYLIDÈNE PRÉSENTANT UNE FAIBLE Tg ET PROCÉDÉS POUR LEURS PRÉPARATIONS |
JP2003086202A (ja) * | 2001-09-14 | 2003-03-20 | Central Glass Co Ltd | 電気化学ディバイス用固体高分子電解質及びその製造法 |
WO2003022892A2 (fr) * | 2001-09-01 | 2003-03-20 | Universität Stuttgart Institut Für Chemische Verfahrenstechnik | Oligomeres et polymeres contenant des groupes sulfinate et procedes de fabrication de ces composes |
US6896777B2 (en) | 2001-02-26 | 2005-05-24 | Solvay Solexis S.P.A. | Porous hydrophilic membranes |
US6902676B2 (en) | 2001-02-26 | 2005-06-07 | Ausimont S.P.A. | Porous hydrophilic membranes |
US6921482B1 (en) * | 1999-01-29 | 2005-07-26 | Mykrolis Corporation | Skinned hollow fiber membrane and method of manufacture |
EP1845125A1 (fr) * | 2006-04-12 | 2007-10-17 | Asahi Glass Company, Limited | Film pour structure de membrane |
US7648034B2 (en) | 2001-04-27 | 2010-01-19 | Millipore Corporation | Coated membranes and other articles |
US7649025B2 (en) | 2002-10-17 | 2010-01-19 | Toyo Boseki Kabushiki Kaisha | Composite ion-exchange membrane |
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WO2018077668A1 (fr) * | 2016-10-28 | 2018-05-03 | Solvay Specialty Polymers Italy S.P.A. | Procédé de réticulation de polymères |
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JP4899238B2 (ja) * | 2000-06-21 | 2012-03-21 | 株式会社豊田中央研究所 | 複合化架橋電解質 |
CA2328433A1 (fr) * | 2000-12-20 | 2002-06-20 | Hydro-Quebec | Elastomeres nitriles fluorosulfones reticulables a faible tg a base de fluorure de vinylidene et ne contenant ni du tetrafluoroethylene ni de groupement siloxane |
US20020160272A1 (en) * | 2001-02-23 | 2002-10-31 | Kabushiki Kaisha Toyota Chuo | Process for producing a modified electrolyte and the modified electrolyte |
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US8058319B2 (en) | 2006-06-01 | 2011-11-15 | E.I. Du Pont De Nemours And Company | Process to prepare fluoropolymer dispersions and membranes |
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US20070281198A1 (en) * | 2006-06-01 | 2007-12-06 | Lousenberg Robert D | Membranes electrode assemblies prepared from fluoropolymer dispersions |
JP2009269960A (ja) * | 2008-05-01 | 2009-11-19 | Tokyo Institute Of Technology | 塩構造を有するポリマー、およびその製造方法 |
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US5691081A (en) | 1995-09-21 | 1997-11-25 | Minnesota Mining And Manufacturing Company | Battery containing bis(perfluoroalkylsulfonyl)imide and cyclic perfluoroalkylene disulfonylimide salts |
US5795496A (en) | 1995-11-22 | 1998-08-18 | California Institute Of Technology | Polymer material for electrolytic membranes in fuel cells |
US5962546A (en) | 1996-03-26 | 1999-10-05 | 3M Innovative Properties Company | Cationically polymerizable compositions capable of being coated by electrostatic assistance |
EP1312603A1 (fr) | 1998-01-30 | 2003-05-21 | Hydro-Quebec | Dérivés bis-sulfonyles polymérisables et leur utilisation dans la préparation de membranes échangeuses d'ions |
US6090895A (en) | 1998-05-22 | 2000-07-18 | 3M Innovative Properties Co., | Crosslinked ion conductive membranes |
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- 1999-01-29 EP EP99902478A patent/EP0973809B1/fr not_active Expired - Lifetime
- 1999-01-29 WO PCT/CA1999/000078 patent/WO1999038897A1/fr active IP Right Grant
- 1999-01-29 DE DE69916715T patent/DE69916715T2/de not_active Expired - Lifetime
- 1999-01-29 DE DE69940033T patent/DE69940033D1/de not_active Expired - Lifetime
- 1999-01-29 EP EP03024852A patent/EP1400539B1/fr not_active Expired - Lifetime
- 1999-01-29 JP JP53874999A patent/JP4477149B2/ja not_active Expired - Lifetime
- 1999-09-07 US US09/390,648 patent/US6670424B1/en not_active Expired - Lifetime
-
2001
- 2001-07-18 US US09/906,702 patent/US20020002240A1/en not_active Abandoned
-
2002
- 2002-03-08 US US10/094,047 patent/US6649703B2/en not_active Expired - Lifetime
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2003
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Cited By (24)
Publication number | Priority date | Publication date | Assignee | Title |
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US6090895A (en) * | 1998-05-22 | 2000-07-18 | 3M Innovative Properties Co., | Crosslinked ion conductive membranes |
US6921482B1 (en) * | 1999-01-29 | 2005-07-26 | Mykrolis Corporation | Skinned hollow fiber membrane and method of manufacture |
US7288600B2 (en) | 1999-10-12 | 2007-10-30 | Entegris, Inc. | Fluorocarbon polymeric compositions having hydrophilic functional groups and process |
WO2001027167A1 (fr) * | 1999-10-12 | 2001-04-19 | Millipore Corporation | Compositions polymeres de fluorocarbone possedant des groupes fonctionnels hydrophiles et procede |
JP2001319521A (ja) * | 2000-05-09 | 2001-11-16 | Toyota Central Res & Dev Lab Inc | 電解質の改質方法及び改質電解質 |
JP4595159B2 (ja) * | 2000-05-09 | 2010-12-08 | 株式会社豊田中央研究所 | 電解質の改質方法及び改質電解質 |
WO2001096268A2 (fr) * | 2000-06-13 | 2001-12-20 | HYDRO-QUéBEC | ÉLASTOMÈRES RÉTICULABLES FLUORÉS BROMOSULFONÉS À BASE DE FLUORURE DE VINYLIDÈNE PRÉSENTANT UNE FAIBLE Tg ET PROCÉDÉS POUR LEURS PRÉPARATIONS |
WO2001096268A3 (fr) * | 2000-06-13 | 2002-05-16 | Hydro Quebec | ÉLASTOMÈRES RÉTICULABLES FLUORÉS BROMOSULFONÉS À BASE DE FLUORURE DE VINYLIDÈNE PRÉSENTANT UNE FAIBLE Tg ET PROCÉDÉS POUR LEURS PRÉPARATIONS |
US6896777B2 (en) | 2001-02-26 | 2005-05-24 | Solvay Solexis S.P.A. | Porous hydrophilic membranes |
US6902676B2 (en) | 2001-02-26 | 2005-06-07 | Ausimont S.P.A. | Porous hydrophilic membranes |
US7648034B2 (en) | 2001-04-27 | 2010-01-19 | Millipore Corporation | Coated membranes and other articles |
WO2003022892A2 (fr) * | 2001-09-01 | 2003-03-20 | Universität Stuttgart Institut Für Chemische Verfahrenstechnik | Oligomeres et polymeres contenant des groupes sulfinate et procedes de fabrication de ces composes |
WO2003022892A3 (fr) * | 2001-09-01 | 2003-08-14 | Univ Stuttgart Inst Fuer Chemi | Oligomeres et polymeres contenant des groupes sulfinate et procedes de fabrication de ces composes |
JP2003086202A (ja) * | 2001-09-14 | 2003-03-20 | Central Glass Co Ltd | 電気化学ディバイス用固体高分子電解質及びその製造法 |
US7649025B2 (en) | 2002-10-17 | 2010-01-19 | Toyo Boseki Kabushiki Kaisha | Composite ion-exchange membrane |
EP1845125A1 (fr) * | 2006-04-12 | 2007-10-17 | Asahi Glass Company, Limited | Film pour structure de membrane |
US7732045B2 (en) | 2006-04-12 | 2010-06-08 | Asahi Glass Company, Limited | Film for membrane structure |
WO2010117845A2 (fr) | 2009-04-06 | 2010-10-14 | Entegris, Inc. | Membranes poreuses non démouillées |
US9359480B2 (en) | 2009-04-06 | 2016-06-07 | Entegris, Inc. | Non-dewetting porous membranes |
US10179842B2 (en) | 2009-04-06 | 2019-01-15 | Entegris, Inc. | Non-dewetting porous membranes |
WO2018077668A1 (fr) * | 2016-10-28 | 2018-05-03 | Solvay Specialty Polymers Italy S.P.A. | Procédé de réticulation de polymères |
KR20190077404A (ko) * | 2016-10-28 | 2019-07-03 | 솔베이 스페셜티 폴리머스 이태리 에스.피.에이. | 중합체의 가교 방법 |
US11059922B2 (en) | 2016-10-28 | 2021-07-13 | Solvay Specialty Polymers Italy S.P.A. | Method for cross-linking polymers |
KR102487719B1 (ko) | 2016-10-28 | 2023-01-16 | 솔베이 스페셜티 폴리머스 이태리 에스.피.에이. | 중합체의 가교 방법 |
Also Published As
Publication number | Publication date |
---|---|
DE69940033D1 (de) | 2009-01-15 |
DE69916715D1 (de) | 2004-06-03 |
US6670424B1 (en) | 2003-12-30 |
US7034082B2 (en) | 2006-04-25 |
EP0973809B1 (fr) | 2004-04-28 |
US20020002240A1 (en) | 2002-01-03 |
US20050027022A1 (en) | 2005-02-03 |
US6649703B2 (en) | 2003-11-18 |
US20020091201A1 (en) | 2002-07-11 |
EP1400539A1 (fr) | 2004-03-24 |
EP1400539B1 (fr) | 2008-12-03 |
DE69916715T2 (de) | 2005-04-21 |
US20070010628A1 (en) | 2007-01-11 |
JP2001522401A (ja) | 2001-11-13 |
EP0973809A1 (fr) | 2000-01-26 |
JP4477149B2 (ja) | 2010-06-09 |
US7674560B2 (en) | 2010-03-09 |
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