EP1490429A2 - Compositions a base de polymeres cationiques a groupes amidinium et de liquides ioniques - Google Patents

Compositions a base de polymeres cationiques a groupes amidinium et de liquides ioniques

Info

Publication number
EP1490429A2
EP1490429A2 EP03704653A EP03704653A EP1490429A2 EP 1490429 A2 EP1490429 A2 EP 1490429A2 EP 03704653 A EP03704653 A EP 03704653A EP 03704653 A EP03704653 A EP 03704653A EP 1490429 A2 EP1490429 A2 EP 1490429A2
Authority
EP
European Patent Office
Prior art keywords
alkyl
composition according
polymer
group
aryl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP03704653A
Other languages
German (de)
English (en)
Inventor
Friedrich-Georg Schmidt
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Evonik Operations GmbH
Original Assignee
CREAVIS GESELLSCHAFT fur TECHNOLOGIEUND INNOVATION MBH
CREAVIS GES fur TECHNOLOGIEUN
Creavis Gesellschaft fuer Technologie und Innovation mbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by CREAVIS GESELLSCHAFT fur TECHNOLOGIEUND INNOVATION MBH, CREAVIS GES fur TECHNOLOGIEUN, Creavis Gesellschaft fuer Technologie und Innovation mbH filed Critical CREAVIS GESELLSCHAFT fur TECHNOLOGIEUND INNOVATION MBH
Publication of EP1490429A2 publication Critical patent/EP1490429A2/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L101/00—Compositions of unspecified macromolecular compounds
    • C08L101/12—Compositions of unspecified macromolecular compounds characterised by physical features, e.g. anisotropy, viscosity or electrical conductivity
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/02—Polyamines
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
    • C08L79/02—Polyamines

Definitions

  • the present invention relates to compositions containing cationic polymers with cyclic non-aromatic units which have an amidinium group and an ionic liquid and their use.
  • Ionic liquids have been the subject of various research projects for several years.
  • An ionic liquid is generally understood to be a liquid that consists exclusively of ions.
  • ionic liquids are liquid and relatively low-viscosity even at low temperatures ( ⁇ 100 ° C).
  • high-temperature salt melts have been successfully used as reaction media in preparative applications, the fact that ionic liquids are already in the liquid state below 100 ° C allows them to be used as a replacement for conventional organic solvents in chemical processes.
  • Immobilized ionic liquids are known for example from EP-A-0 553 009 and US-A-5,693,585. Both references describe a calcined support containing an ionic liquid consisting of aluminum chloride and an alkylated ammonium chloride or imidazolium chloride. The immobilized ionic liquids are used as catalysts in alkylation reactions.
  • WO-A-01/32308 describes ionic liquids which are immobilized on a functionalized carrier which carries or contains a component of the ionic liquid or a precursor of such a component.
  • the ionic liquid can be immobilized on the anion by treating a carrier with an anion source before the ionic liquid is applied or formed.
  • the ionic liquid can be immobilized in that the cation is covalently bound to the support or is embedded in the support.
  • the immobilized ionic liquids are used as catalysts, e.g. B. used for the Friedel-Crafts reaction.
  • a polymer complex which consists of a polypyridinium salt and as an ionic liquid of a pyridinium salt and aluminum chloride.
  • the polypyridinium salt in this case represents the ionic liquid instead of the pyridinium salt and enables the polymer complexes to form thin layers, which results from the enormous increase in viscosity compared to the pure ionic liquid.
  • the new polymer complexes have a high ionic conductivity and, like other polymer electrolytes, are of interest for use in batteries and display devices.
  • US-A-6,025,457 discloses "molten salt type" polyelectrolytes which contain a molten salt polymer which is formed by reacting an imidazolium derivative bearing a substituent at the 1- and 3-positions with at least one organic acid or an organic acid compound having an acid amide or acid imide bond is obtained, wherein at least one component, i.e. H. said imidazolium derivative or said organic acid compound is a polymerizable monomer or a polymer.
  • These polyelectrolytes also show high ionic conductivity at room temperature and have good mechanical properties.
  • JP-A-10265673 discloses the production of solid polymer electrolytes in the form of ion-conducting films by polymerizing hydroxyethyl methacrylate and ethylene glycol dimethacrylate in the presence of an ionic liquid based on 1-butylpyridinium tetrafluoroborate.
  • JP-A-10265674 relates to compositions of polymers e.g. As polyacrylonitrile and polyethylene oxide, and ionic liquids.
  • the ionic liquids contain, for example, LiBF 4 and l-ethyl-3-methylimidazolium tetrafluoroborate) Solid electrolytes, antistatic agents and shields are given as uses.
  • Watanabe et al. in Solid State Ionics 86-88 (1996), 353-356 disclose that salt mixtures of trimethylmethylammonium benzoate, lithium acetate and lithium bis (trifluoromethylsulfonyl) imide which are liquid at temperatures below 100 ° C. are compatible with polyacrylonitrile and polyvinylbutyral and result in systems , from which film-forming polymer electrolytes can be produced.
  • a disadvantage of the mixtures of nonionic polymer and ionic liquid is that the ion density is not too high.
  • the object of the present invention is to provide a new polymer composition which u. a. high ion density, i. H. good conductivity, with adjustable glass transition temperature and good processability and manufacturability.
  • composition which contains a cationic polymer with cyclic non-aromatic units which contain an amidinium group and an ionic liquid fulfills this task.
  • the cyclic non-aromatic units of the cationic polymer which contain an amidinium group can be arranged in the main chain of the polymer, in the side chains of the polymer or in both the main chain and in the side chains.
  • the cyclic non-aromatic units which contain an amidinium group are preferably substituted or unsubstituted 5-, 6- or 7-rings, particularly preferably substituted or unsubstituted imidazolinium, tetrahydropyrimidium and tetrahydro-1,3 diazepinium groups, with imidazolinium and tetrahydropyrimidinium groups being most preferred.
  • the cyclic non-aromatic units can also be 8 rings or larger rings.
  • the cyclic non-aromatic units of the cationic polymer which contain an amidinium group, are arranged in the main chain of the polymer. They can then be linked to the main chain via C or N atoms of the cyclic unit.
  • the cyclic non-aromatic units which contain an amidinium group are preferably linked via the two N atoms to the main chain of the polymer.
  • a cationic polymer which contains the following structural unit in the main chain is particularly advantageous:
  • N 2 is particularly preferred, ie the cyclic non-aromatic units which contain an amidinium group are preferably imidazolinium groups. Alternatively, however, the cyclic non-aromatic units which contain an amidinium group can also be present in the side chains of the polymer.
  • the type of polymer ie the structure of the main chain, is not essential to the invention.
  • Illustrative examples of polymer skeletons with side chains which contain the cyclic non-aromatic units which contain an amidinium group are vinyl polymers, in particular polyacrylates, polyglycosides, polyorganosiloxanes, polyethers, polyesters, polyamides and polyurethanes.
  • the main chain can of course also be constructed from different structural units, so that the corresponding copolymers are present.
  • the cyclic non-aromatic units which contain an amidinium group and are arranged in the side chains of the polymer can have the following structures, for example:
  • R 5 is selected from H, -CH 3 , -C 2 H 5 , -C 3 H 7 and -C 4 H and can be the same or different within one unit;
  • R 6 is an unbranched or branched alkyl radical having 1 to 18 carbon atoms and can be the same or different within one unit, and
  • R 7 is H or R 6 .
  • compositions which contain cationic polymers with different cyclic non-aromatic units which have an amidinium group also fall under the present invention.
  • the weight average molecular weight of the cationic polymer in a preferred embodiment is 500 to 1,500,000, more preferably 500 to 200,000 and most preferably 20,000 to 50,000.
  • the counterions of the cationic polymer can be any anion that does not react with the cationic polymer; mixtures of different anions are also suitable.
  • Suitable anions include halide, i. H. Chloride, bromide and iodide, preferably iodide; Phosphate; Halogenophosphates, preferably hexafluorophosphate;
  • alkyl phosphates Nitrate; Sulfate; Bisulfate; alkyl sulfates; aryl sulfates; perfluorinated aryl and alkyl sulfates, preferably octyl sulfate; Sulfonate, alkyl sulfonates; arylsulphonates; perfluorinated aryl and alkyl sulfonates, preferably triflate; perchlorate;
  • Tetrarchloroaluminat tetrafluoroborate
  • Alkyl borates preferably B (C 2 H 5 ) 3 C 6 H ⁇ 3 ⁇
  • tosylate saccharinate
  • Alkyl carboxylates and bis (perfluoroalkylsulfonyl) amide anions preferably that
  • the most preferred counterions are iodide, hexafluorophosphate, alkyl sulfates, especially octyl sulfate, tetrafluoroborate and the bis (trifluoromethylsulfonyl) amide anion.
  • the counterion of the cationic polymer can be an anion which is suitable for generating liquid-crystalline states, for example an anion of the general formula
  • H / O means that the rings can independently be aromatic or saturated; r and s are each independently 0, 1 or 2 and r + s>2; z is a single bond, -C 2 H 2 -, -C 2 H5-, -CF 2 O-, -OCF 2 -,
  • R and R are each, independently of one another, an unsubstituted alkyl radical having up to 15 C atoms, a single radical having -C ⁇ or -CF 3 or an at least monosubstituted alkyl radical having up to 15 C atoms, with one or several -CH 2 groups each independently of one another by -O-, -S-, -C ⁇ C-, -CO-,
  • a preferred liquid crystal phase forming anion has the following general formula:
  • compositions according to the invention Mixtures of different polymers with cyclic non-aromatic units containing an amidinium group or mixtures of one or more polymers with cyclic non-aromatic units containing an amidinium group with another polymer can also be used in the compositions according to the invention.
  • cationic polymers bearing the cyclic non-aromatic moieties in the side chains can be blended with an uncharged polymer that conforms to or is similar to the main chain structure of the cationic polymer.
  • the cationic polymers with cyclic non-aromatic units which contain an amidinium group can be prepared by various processes.
  • a monomer which already contains the cyclic non-aromatic units which contain an amidinium group or a non-quaternized amidine group in the polymerization reaction which leads to polymers with the cationic amidinium groups in the side chains, there are also those Possibility of introducing the cyclic non-aromatic units which contain an amidinium group only after the actual polymerization reaction.
  • a cyclic amidinium group into a side chain of the polymer
  • R 4 , R 5 , R 6 , R 7 and u are defined as before for structures (II) and (III); Et stands for the ethyl radical and X " is a weakly nucleophilic anion, for example tetrafluoroborate or hexafluorophosphate
  • X is a weakly nucleophilic anion, for example tetrafluoroborate or hexafluorophosphate
  • Polymers with imidazolinium, tetrahydropyrimidinium and tetrahydro-1,3-diacepinium groups in the main chain can also be prepared by reaction with an orthoester.
  • an orthoester for example, the reaction of linear or predominantly linear polyethylene amine with an orthoester according to the following scheme (iii)
  • Polymers in which the cyclic non-aromatic units are arranged in the main chain and linked to it via C atoms can also be prepared by reaction with an orthoester.
  • an orthoester preferably an orthoethyl ester
  • the reaction of polyvinylamine with an orthoester, preferably an orthoethyl ester, according to scheme (iv) leads to a cationic polymer with tetrahydropyrimidinium groups in the main chain.
  • R 3 is as defined for structural unit (I).
  • the anions X " introduced in the synthesis with orthoesters can later be exchanged for other desired counterions.
  • the cationic polymers can have different states of aggregation, from liquid to soft, gel-like, glass-like, hard to partially crystalline. Due to the ion density and the type of anions, as well as the hydrophilicity of the polymer, u. a. the electrical properties, such as B. influences the ionic conductivity or the specific volume resistance.
  • the ionic liquid is preferably a salt with a cation selected from imidazolium ions, pyridinium ions, ammonium ions and phosphonium ions according to the following structures
  • R and R ' are each independently H, an alkyl, olefin or aryl group, or from substituted or unsubstituted imdidazolinium, tetrahydropyrimidinium and tetrahydro-l, 3-diazepinium ions, and an anion selected from the group Group consisting of halides, ie chloride, bromide and iodide, preferably iodide; Phosphate; Halogenophosphates, preferably hexafluorophosphate; alkyl phosphates; Nitrate; Sulfate; Bisulfate; Alkyl sulfates, preferably octyl sulfate; aryl sulfates; perfluorinated aryl and alkyl sulfates; Sulfonate, alkyl sulfonates; arylsulphonates; perfluorinated aryl and alkyl sulfonates,
  • Preferred anions of the ionic liquid are iodide, hexafluorophosphate, alkyl sulfates, in particular octyl sulfate, tetrafluoroborate and the bis (trifluoromethylsulfonyl) amide anion.
  • compositions according to the invention can be prepared using the customary methods known to those skilled in the art. Examples include:
  • composition according to the invention has a high ionic conductivity and is easy to process.
  • an ionic liquid in the composition according to the invention brings about a decrease in the intra- and intermolecular interactions between the functional groups of the cationic polymer and thus generally
  • the ionic liquid thus acts as a plasticizer in the cationic polymer. Increasing the fluidity of the melt of the cationic
  • Polymers is given by the solvent-like character of the ionic liquids, the particular advantage in the non-volatility of the ionic liquids also in the
  • Processing temperatures of the composition It can either
  • Processing temperatures are used at which the previously used plasticizers or processing aids already have an excessively high vapor pressure and lead to outgassing, or the cationic polymer can be caused by the plasticizing
  • a decisive advantage of the present invention is that the ionic liquid - in contrast to previously known plasticizers - does not negatively or only positively influence the conductivity of the cationic polymer in the composition.
  • the electrical properties of the composition according to the invention can be adapted over a wide range by selecting the cations and anions used, which can produce antistatic and, in some cases, semiconducting properties.
  • compositions according to the invention improves the adhesive behavior of the composition according to the invention to polar surfaces or surfaces swollen or dissolved by the ionic liquid. From the above-mentioned special advantages of the compositions according to the invention, depending on their specific properties, there are many different possible uses of the compositions, e.g. B.
  • composition of the invention can also be used as a miscible or self-segregating additive for other polymers, for example to modify the viscosity (i.e. as a plasticizer) and / or the conductivity.
  • a plasticizer i.e. as a plasticizer
  • This enables, for example, the thermoplastic processing of various polymers, which would otherwise be very difficult or impossible at all, e.g. B. of polyaramides, ionomers, polyesters, polyamides and polyether ketones.
  • the cationic polymer is ionically bound to liquid-crystal phase-forming anions
  • liquid-crystalline polymers are obtained in combination with ionic liquids, which enable simple production of thin layers and the adjustment of their optical and thermal properties.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Secondary Cells (AREA)
  • Hybrid Cells (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
  • Conductive Materials (AREA)
  • Primary Cells (AREA)

Abstract

La présente invention concerne des compositions qui renferment un liquide ionique et un polymère cationique à unités cycliques non aromatiques présentant un groupe amidinium, ainsi que l'utilisation de ces compositions.
EP03704653A 2002-04-04 2003-02-19 Compositions a base de polymeres cationiques a groupes amidinium et de liquides ioniques Withdrawn EP1490429A2 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10214872 2002-04-04
DE10214872A DE10214872A1 (de) 2002-04-04 2002-04-04 Zusammensetzungen aus kationischen Polymeren mit Amidinium-Gruppen und ionischen Flüssigkeiten
PCT/EP2003/001652 WO2003085050A2 (fr) 2002-04-04 2003-02-19 Compositions a base de polymeres cationiques a groupes amidinium et de liquides ioniques

Publications (1)

Publication Number Publication Date
EP1490429A2 true EP1490429A2 (fr) 2004-12-29

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Country Status (8)

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US (1) US20050143517A1 (fr)
EP (1) EP1490429A2 (fr)
JP (1) JP2005527667A (fr)
CN (1) CN1643051A (fr)
AU (1) AU2003206925A1 (fr)
CA (1) CA2479941A1 (fr)
DE (1) DE10214872A1 (fr)
WO (1) WO2003085050A2 (fr)

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Publication number Publication date
WO2003085050A2 (fr) 2003-10-16
DE10214872A1 (de) 2003-10-16
JP2005527667A (ja) 2005-09-15
US20050143517A1 (en) 2005-06-30
AU2003206925A8 (en) 2003-10-20
WO2003085050A3 (fr) 2004-03-25
CN1643051A (zh) 2005-07-20
CA2479941A1 (fr) 2003-10-16
AU2003206925A1 (en) 2003-10-20

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